AU3602901A - Novel color former and recording material - Google Patents
Novel color former and recording material Download PDFInfo
- Publication number
- AU3602901A AU3602901A AU36029/01A AU3602901A AU3602901A AU 3602901 A AU3602901 A AU 3602901A AU 36029/01 A AU36029/01 A AU 36029/01A AU 3602901 A AU3602901 A AU 3602901A AU 3602901 A AU3602901 A AU 3602901A
- Authority
- AU
- Australia
- Prior art keywords
- group
- compound
- urea
- urethane
- heat
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000463 material Substances 0.000 title claims description 205
- -1 urea-urethane compound Chemical class 0.000 claims description 579
- 150000001875 compounds Chemical class 0.000 claims description 258
- 239000000203 mixture Substances 0.000 claims description 203
- 239000010410 layer Substances 0.000 claims description 112
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 110
- 239000012948 isocyanate Substances 0.000 claims description 109
- OYQYHJRSHHYEIG-UHFFFAOYSA-N ethyl carbamate;urea Chemical compound NC(N)=O.CCOC(N)=O OYQYHJRSHHYEIG-UHFFFAOYSA-N 0.000 claims description 101
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 100
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 88
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 87
- 239000000975 dye Substances 0.000 claims description 81
- 239000005056 polyisocyanate Substances 0.000 claims description 81
- 229920001228 polyisocyanate Polymers 0.000 claims description 81
- 125000003277 amino group Chemical group 0.000 claims description 74
- 238000000034 method Methods 0.000 claims description 74
- 238000006243 chemical reaction Methods 0.000 claims description 70
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 65
- 150000007824 aliphatic compounds Chemical group 0.000 claims description 63
- 150000001491 aromatic compounds Chemical group 0.000 claims description 62
- 239000000758 substrate Substances 0.000 claims description 59
- 125000001424 substituent group Chemical group 0.000 claims description 57
- 150000002391 heterocyclic compounds Chemical group 0.000 claims description 55
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 50
- 239000002243 precursor Substances 0.000 claims description 49
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 48
- 230000008569 process Effects 0.000 claims description 48
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 150000003457 sulfones Chemical class 0.000 claims description 44
- 125000005843 halogen group Chemical group 0.000 claims description 42
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 40
- 239000002253 acid Substances 0.000 claims description 36
- 239000002904 solvent Substances 0.000 claims description 35
- 125000002560 nitrile group Chemical group 0.000 claims description 29
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 29
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 28
- 230000035945 sensitivity Effects 0.000 claims description 27
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 27
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 25
- 150000002989 phenols Chemical class 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 239000002270 dispersing agent Substances 0.000 claims description 23
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 229920003169 water-soluble polymer Polymers 0.000 claims description 20
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 19
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 229920000609 methyl cellulose Polymers 0.000 claims description 18
- 239000001923 methylcellulose Substances 0.000 claims description 18
- 235000010981 methylcellulose Nutrition 0.000 claims description 18
- 238000000576 coating method Methods 0.000 claims description 17
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 17
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 17
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 17
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 17
- 238000010330 laser marking Methods 0.000 claims description 17
- 230000005291 magnetic effect Effects 0.000 claims description 17
- 230000002378 acidificating effect Effects 0.000 claims description 16
- 239000011248 coating agent Substances 0.000 claims description 16
- 239000011247 coating layer Substances 0.000 claims description 16
- 238000000227 grinding Methods 0.000 claims description 16
- 239000000543 intermediate Substances 0.000 claims description 16
- 238000011161 development Methods 0.000 claims description 15
- 239000003085 diluting agent Substances 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000004202 carbamide Substances 0.000 claims description 14
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 14
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 13
- 239000012790 adhesive layer Substances 0.000 claims description 13
- 239000001023 inorganic pigment Substances 0.000 claims description 13
- 239000011241 protective layer Substances 0.000 claims description 13
- 239000003945 anionic surfactant Substances 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 12
- 238000002844 melting Methods 0.000 claims description 12
- 230000008018 melting Effects 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- ZTILAOCGFRDHBH-UHFFFAOYSA-N 4-(4-propan-2-yloxyphenyl)sulfonylphenol Chemical compound C1=CC(OC(C)C)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 ZTILAOCGFRDHBH-UHFFFAOYSA-N 0.000 claims description 11
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 11
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 claims description 10
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 10
- 239000007850 fluorescent dye Substances 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 claims description 10
- 239000011230 binding agent Substances 0.000 claims description 9
- HETXQHOFMGVMJT-UHFFFAOYSA-L disodium;2-(2-ethylhexyl)-2-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCC(CC)CC(S(O)(=O)=O)(C([O-])=O)CC([O-])=O HETXQHOFMGVMJT-UHFFFAOYSA-L 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 239000012860 organic pigment Substances 0.000 claims description 9
- 239000002245 particle Substances 0.000 claims description 9
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 150000003863 ammonium salts Chemical class 0.000 claims description 8
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 8
- 239000000194 fatty acid Substances 0.000 claims description 8
- 229930195729 fatty acid Natural products 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 7
- 229920001223 polyethylene glycol Polymers 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 claims description 6
- 229940037312 stearamide Drugs 0.000 claims description 5
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 4
- AGPLQTQFIZBOLI-UHFFFAOYSA-N 1-benzyl-4-phenylbenzene Chemical group C=1C=C(C=2C=CC=CC=2)C=CC=1CC1=CC=CC=C1 AGPLQTQFIZBOLI-UHFFFAOYSA-N 0.000 claims description 4
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 claims description 4
- 239000005995 Aluminium silicate Substances 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- 235000012211 aluminium silicate Nutrition 0.000 claims description 4
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002736 nonionic surfactant Substances 0.000 claims description 4
- 230000002441 reversible effect Effects 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 239000000314 lubricant Substances 0.000 claims description 3
- JTWBMEAENZGSOQ-UHFFFAOYSA-N 1,2-bis(phenoxymethyl)benzene Chemical compound C=1C=CC=C(COC=2C=CC=CC=2)C=1COC1=CC=CC=C1 JTWBMEAENZGSOQ-UHFFFAOYSA-N 0.000 claims description 2
- LROZSPADHSXFJA-UHFFFAOYSA-N 2-(4-hydroxyphenyl)sulfonylphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=CC=C1O LROZSPADHSXFJA-UHFFFAOYSA-N 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 235000019646 color tone Nutrition 0.000 claims description 2
- YGANSGVIUGARFR-UHFFFAOYSA-N dipotassium dioxosilane oxo(oxoalumanyloxy)alumane oxygen(2-) Chemical compound [O--].[K+].[K+].O=[Si]=O.O=[Al]O[Al]=O YGANSGVIUGARFR-UHFFFAOYSA-N 0.000 claims description 2
- 230000009477 glass transition Effects 0.000 claims description 2
- 230000001678 irradiating effect Effects 0.000 claims description 2
- 229910052627 muscovite Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000005022 packaging material Substances 0.000 claims description 2
- 239000010456 wollastonite Substances 0.000 claims description 2
- 229910052882 wollastonite Inorganic materials 0.000 claims description 2
- 238000009740 moulding (composite fabrication) Methods 0.000 claims 11
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- 229920005862 polyol Polymers 0.000 description 125
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 114
- 150000003077 polyols Chemical class 0.000 description 99
- 150000002513 isocyanates Chemical class 0.000 description 52
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 46
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 43
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 43
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 42
- 125000005442 diisocyanate group Chemical group 0.000 description 36
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 29
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 27
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 22
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 22
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- 229960004063 propylene glycol Drugs 0.000 description 19
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 17
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- MERLDGDYUMSLAY-UHFFFAOYSA-N 4-[(4-aminophenyl)disulfanyl]aniline Chemical compound C1=CC(N)=CC=C1SSC1=CC=C(N)C=C1 MERLDGDYUMSLAY-UHFFFAOYSA-N 0.000 description 12
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- YIMHRDBSVCPJOV-UHFFFAOYSA-N n'-(2-ethoxyphenyl)-n-(2-ethylphenyl)oxamide Chemical compound CCOC1=CC=CC=C1NC(=O)C(=O)NC1=CC=CC=C1CC YIMHRDBSVCPJOV-UHFFFAOYSA-N 0.000 description 1
- IAHNAHJRZNELLZ-UHFFFAOYSA-N n'-(2-methoxyphenyl)acetohydrazide Chemical compound COC1=CC=CC=C1NNC(C)=O IAHNAHJRZNELLZ-UHFFFAOYSA-N 0.000 description 1
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 1
- AUNYWGYRPIHMLM-UHFFFAOYSA-N n,1-diphenylmethanesulfonamide Chemical compound C=1C=CC=CC=1NS(=O)(=O)CC1=CC=CC=C1 AUNYWGYRPIHMLM-UHFFFAOYSA-N 0.000 description 1
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 1
- SHERLLWHOMUAER-UHFFFAOYSA-N n,n,2-trifluoroaniline Chemical compound FN(F)C1=CC=CC=C1F SHERLLWHOMUAER-UHFFFAOYSA-N 0.000 description 1
- ZDKHHQLHSMKXJO-UHFFFAOYSA-N n,n-dichloro-4-nitroaniline Chemical compound [O-][N+](=O)C1=CC=C(N(Cl)Cl)C=C1 ZDKHHQLHSMKXJO-UHFFFAOYSA-N 0.000 description 1
- DADSZOFTIIETSV-UHFFFAOYSA-N n,n-dichloroaniline Chemical compound ClN(Cl)C1=CC=CC=C1 DADSZOFTIIETSV-UHFFFAOYSA-N 0.000 description 1
- FSUMZUVANZAHBW-UHFFFAOYSA-N n,n-dimethoxyaniline Chemical compound CON(OC)C1=CC=CC=C1 FSUMZUVANZAHBW-UHFFFAOYSA-N 0.000 description 1
- KESXDDATSRRGAH-UHFFFAOYSA-N n-(4-hydroxyphenyl)butanamide Chemical compound CCCC(=O)NC1=CC=C(O)C=C1 KESXDDATSRRGAH-UHFFFAOYSA-N 0.000 description 1
- JVKWTDRHWOSRFT-UHFFFAOYSA-N n-(4-hydroxyphenyl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)NC1=CC=C(O)C=C1 JVKWTDRHWOSRFT-UHFFFAOYSA-N 0.000 description 1
- YASWBJXTHOXPGK-UHFFFAOYSA-N n-(4-hydroxyphenyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC1=CC=C(O)C=C1 YASWBJXTHOXPGK-UHFFFAOYSA-N 0.000 description 1
- JHOKTNSTUVKGJC-UHFFFAOYSA-N n-(hydroxymethyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCO JHOKTNSTUVKGJC-UHFFFAOYSA-N 0.000 description 1
- ZBCKLHSPIVVGMC-UHFFFAOYSA-N n-benzyl-n-fluoro-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(F)CC1=CC=CC=C1 ZBCKLHSPIVVGMC-UHFFFAOYSA-N 0.000 description 1
- JQBUMIBAURQBNA-UHFFFAOYSA-N n-butyl-2-hydroxybenzamide Chemical compound CCCCNC(=O)C1=CC=CC=C1O JQBUMIBAURQBNA-UHFFFAOYSA-N 0.000 description 1
- LCTOXAHEDJCUII-UHFFFAOYSA-N n-carbamoyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC(N)=O LCTOXAHEDJCUII-UHFFFAOYSA-N 0.000 description 1
- QEZIFBAXJMHDJP-UHFFFAOYSA-N n-chloro-4-fluoroaniline Chemical compound FC1=CC=C(NCl)C=C1 QEZIFBAXJMHDJP-UHFFFAOYSA-N 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- LCOZBMUWOGOTLA-UHFFFAOYSA-N n-fluoro-n-(trifluoromethyl)aniline Chemical compound FC(F)(F)N(F)C1=CC=CC=C1 LCOZBMUWOGOTLA-UHFFFAOYSA-N 0.000 description 1
- MEPMBCQGKRXQFC-UHFFFAOYSA-N n-methyl-n'-phenylacetohydrazide Chemical compound CC(=O)N(C)NC1=CC=CC=C1 MEPMBCQGKRXQFC-UHFFFAOYSA-N 0.000 description 1
- GYNAVKULVOETAD-UHFFFAOYSA-N n-phenoxyaniline Chemical compound C=1C=CC=CC=1NOC1=CC=CC=C1 GYNAVKULVOETAD-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- GJNDMSSZEBNLPU-UHFFFAOYSA-N octadecylurea Chemical compound CCCCCCCCCCCCCCCCCCNC(N)=O GJNDMSSZEBNLPU-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- AJCDFVKYMIUXCR-UHFFFAOYSA-N oxobarium;oxo(oxoferriooxy)iron Chemical compound [Ba]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O AJCDFVKYMIUXCR-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- QHDYIMWKSCJTIM-UHFFFAOYSA-N phenyl 1-hydroxynaphthalene-2-carboxylate Chemical compound C1=CC2=CC=CC=C2C(O)=C1C(=O)OC1=CC=CC=C1 QHDYIMWKSCJTIM-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000011827 silicon-based solvent Substances 0.000 description 1
- ZHROMWXOTYBIMF-UHFFFAOYSA-M sodium;1,3,7,9-tetratert-butyl-11-oxido-5h-benzo[d][1,3,2]benzodioxaphosphocine 11-oxide Chemical compound [Na+].C1C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2OP([O-])(=O)OC2=C1C=C(C(C)(C)C)C=C2C(C)(C)C ZHROMWXOTYBIMF-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000003232 water-soluble binding agent Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/42—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/333—Colour developing components therefor, e.g. acidic compounds
- B41M5/3333—Non-macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/40—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
- C07C311/47—Y being a hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
- C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
- C07C317/42—Y being a hetero atom
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/337—Additives; Binders
- B41M5/3375—Non-macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
W w' E5858 367/89 1 DESCRIPTION NOVEL COLOR-PRODUCING COMPOSITION AND RECORDING MATERIAL TECHNICAL FIELD The present invention relates to a novel urea-urethane compound. The present invention relates also to a novel color-producing composition obtained by 5 using the urea-urethane compound, and a recording material obtained by using the color-producing composi tion. The color-producing composition of the present invention is useful as a color-producing 10 composition for recording materials which use a recording energy such as heat, pressure or the like, and the present invention relates to, in particular, a color-producing composition capable of giving an improved storage stability to an uncolored portion (an 15 original recording material surface) and a developed color image, and a recording material, in particular, a heat-sensitive recording material, which is obtained by using the color-producing composition. BACKGROUND ART 20 Various chemical color-producing systems which use a recording energy such as heat, pressure or the like have been known. Of these systems, color- 2 producing systems usually composed of a two-component color-producing system consisting of a colorless or light-colored dye precursor and a developer capable of causing color development on contact with the dye 5 precursor have been known since early times and are commonly utilized in recording materials. There are, for example, pressure-sensitive recording materials which record using pressure, heat-sensitive recording materials which record using heat, and light-sensitive 10 recording materials which record using light. Pressure-sensitive recording materials have been generally used in the planar forms, similar to paper. In general, the pressure-sensitive recording material is obtained by dissolving a dye precursor in a 15 suitable solvent, emulsifying the resulting solution to several microns, and forming the emulsion into micro capsules. A first layer (also referre to herein as upper paper) of paper obtained by coating a substrate with the microcapsules and a second layer (also 20 referred to herein as under paper) of paper obtained by coating another substrate with a developer layer containing a developer are placed one upon the other so that the microcapsule-coated surface and the developer coated surface face each other. When a pressure is 25 applied to the resulting assembly by writing, striking or the like, the microcapsules are destroyed to release the contents including the dye precursor. The dye precursor transfers to the developer layer to come into 3 contact with the developer, so that color development reaction occurs, resulting in recording of an image. In recent years, a heat-sensitive recording method comprising recording by means of heat energy has 5 been often adopted in various information machines such as facsimiles, printers, recorders and the like. A heat-sensitive recording material used in the heat sensitive recording method has many excellent characteristics such as a high whiteness, appearance 10 and feel which are similar to those of ordinary planar paper, and an excellent aptitude for recording, for example, a high color development sensitivity. The heat-sensitive recording method is advantageous, for example, in that an apparatus used in the method is 15 small, requires no maintenance and produces no noise. Therefore, the range of use of the heat-sensitive recording method has been increased in various fields of, for instance, recorders for measurement, facsimiles, printers, terminals of computer, labels, 20 and automatic vending machines for railroad tickets or the like. In the heat-sensitive recording method, a recording material obtained by forming on a substrate a color-producing layer containing a two-component color 25 producing composition is mainly used, and the components of the heat-sensitive composition are brought into contact with each other by treating the recording material with heat supplied as the recording 4 energy from a thermal head, a hot stamp, laser beams or the like, whereby color development and recording are carried out. Many compositions used as the color producing composition are those obtained by using a 5 colorless or light-colored, electron-donating dye precursor (in particular, a leuco dye) and an acidic developer such as a phenolic compound. An example of a recording material obtained by using a dye precursor is thermal paper obtained by using a combination of 10 Crystal Violet lactone and 4,4'-isopropylidenediphenol (bisphenol A) as a heat-sensitive color-producing composition (see U.S. Patent 3539375, etc.). As the dye precursor and developer used in each of the recording methods described above, an 15 electron-donating compound and an electron-accepting compound, respectively, are mainly used. This is because the electron-donating compound and the electron-accepting compound have, for example, the following excellent characteristics: the dye precursor 20 as electron-donating compound and the developer as electron-accepting compound come into contact with each other to give a nearly instantaneous developed color image with a high density; and a nearly white appear ance can be obtained and various hues such as red, 25 orange, yellow, green, blue, black, etc. can be obtained. However, the developed color image obtained is so poor in chemical resistance that the record disappears easily on contact with a plasticizer 5 contained in a plastic sheet or an eraser, or a chemical contained in food or cosmetics. Also the developed color image is so poor in record storage stability that the record fades or, worse yet, 5 disappears when exposed to sunlight for a relatively short period of time. Therefore, color-producing compositions comprising the dye precursor and the developer are limited in their use to a considerable extent, and their improvement is eagerly desired. 10 In recent years, phenolic compounds represented by bisphenol A are considered unsuitable for use because they are likely to be endocrine disrupters, and hence a non-phenolic developer is preferred. 15 For fulfilling such a request, for example, JP-A-59-115887 and U.S. Patent 4521793 disclose recording materials comprising a combination of color producing compositions comprising an aromatic isocyanate compound and an imino compound, as recording 20 materials having a high shelf stability. These refer ences disclose various recording materials in which the two color-producing compositions are brought into contact with each other to be reacted, by application of recording energy such as heat, pressure, light or 25 the like. The references describe the fact that various colors such as red, orange, yellow, light brown, dark brown, etc. can be developed by properly selecting the color-producing compositions. However, 6 in the inventions disclosed in the references, the development of a black color is not yet sufficient and is eagerly desired in the case of recording materials commonly used at present. 5 JP-A-8-2111 and JP-A-8-2112 disclose heat sensitive recording materials having a color-producing layer containing a colorless or light-colored dye precursor and a urea compound, as heat-sensitive recording materials obtained by using a non-phenolic 10 developer. These recording materials, however, give a low coloring density and have an insufficient shelf stability. JP-A-5-116459 discloses a heat-sensitive recording material having a heat-sensitive color 15 producing layer containing a colorless or light-colored dye precursor and a sulfonylurea compound. This recording material, however, gives a low whiteness and has an insufficient shelf stability. DISCLOSURE OF THE INVENTION 20 The present invention is intended to provide a novel urea-urethane compound or urea-urethane composition that exhibits excellent performance characteristics when used as developer in a color producing composition. 25 The present invention is also intended to provide a novel color-producing composition excellent in image preservability and coloring density, and a 7 recording material, in particular, a heat-sensitive recording material, which is obtained by the use of the color-producing composition, by using any of various urea-urethane compounds or urea-urethane compositions. 5 In addition, the present invention relates to a novel color-producing composition possessing further improved performance characteristics by virtue of the addition of various additives to a urea-urethane compound or a urea-urethane composition and a dye 10 precursor, and a recording material obtained by using said color-producing composition. The present inventors earnestly investigated the synthesis of various compounds for color-producing composition and consequently found that specific 15 compounds exhibit surprisingly excellent performance characteristics, whereby the present invention has been accomplished. Furthermore, the present inventors found that specific compounds exhibit surprisingly excellent performance characteristics in combination with a 20 specific dye precursor, whereby the present invention has been accomplished. That is, the present invention is as follows. A first aspect of the invention is directed to a urea-urethane compound characterized by being 25 represented by the following formula (c) and having a molecular weight of 5,000 or less: 8 0 0 C C (c) R-0 N-A 1 -N N-A 2 H H H wherein R is an aliphatic compound residue, A, and A 2 are independently an aromatic compound residue, the nitrogen atoms of the urea group are directly bonded to 5 the carbon atoms, respectively, of the aromatic rings of A, and A 2 , and R, A, and A 2 may have one or more substituents. A second aspect of the invention is directed to a urea-urethane compound characterized by being 10 represented by the following formula (d): 0 0 C (d) R-O N- N N H H H wherein R is an aliphatic compound residue, hydrogen atom(s) of each benzene ring may be replaced by an aroma-tic compound residue, an aliphatic compound 15 residue, a heterocyclic compound residue, a hydroxyl group, a nitro group, a nitrile group, a carbamoyl group, a sulfamoyl group, a carboxyl group, a nitroso group, an amino group, an oxyamino group, a nitroamino group, a hydrazino group, a ureido group, an isocyanate 20 group, a mercapto group, a sulfo group or a halogen 9 atom, and R may have one or more substituents. A third aspect of the invention is directed to a urea-urethane compound characterized by being represented by the following formula (e) or (f), having 5 at least one urethane group and at least one urea group in a total number of not more than 10 and not less than 3, and having a molecular weight of 5,000 or less: 0 0 Il |I /C C /(e) R-O N--Y-N N- -a1 H H H i wherein R is an aliphatic compound residue, Y is an 10 aromatic compound residue, a heterocyclic compound residue or an aliphatic compound residue, a, is an aromatic, heterocyclic or aliphatic compound residue which is different from Y and has a valence of 2 or more, n is an integer of 2 or more, and each of the 15 residues may have one or more substituents; or 0 0 C CI 3i 0 N-Y-N N-Zj H H H L i n wherein Zi and Y are independently an aromatic compound residue or a heterocyclic compound residue, $1 is an aliphatic compound residue having a valence of 2 or 20 more, n is an integer of 2 or more, and each of the 10 residues may have one or more substituents. A fourth aspect of the invention is directed to a urea-urethane compound characterized by being represented by the following formula (g) or (h): 0 0 5 / \ (g) 1--O N N H (H H n wherein hydrogen atom(s) of each benzene ring may be replaced by an aromatic compound residue, an aliphatic compound residue, a heterocyclic compound residue, a hydroxyl group, a nitro group, a nitrile group, a 10 carbamoyl group, a sulfamoyl group, a carboxyl group, a nitroso group, an amino group, an oxyamino group, a nitroamino group, a hydrazino group, a ureido group, an isocyanate group, a mercapto group, a sulfo group or a halogen atom, 0 1 is an aliphatic compound residue having 15 a valence of 2 or more, n is an integer of 2 or more, and each of the residues may have one or more substituents; or 0 0 0 O H K H H Y' H Q H (h) wherein Rs are independently an aliphatic compound 20 residue, hydrogen atom(s) of each benzene ring may be replaced by an aromatic compound residue, an aliphatic 11 compound residue or a heterocyclic compound residue, each of the residues may have one or more substituents, y, is a group selected from the group consisting of -S0 2 -, -0-, - (S) n-, - (CH 2 ) n-, -CO-, -CONH-, -NH-, 5 -CH(COOR 1 )-, -C(CF 3
)
2 -, -CR 2
R
3 - and any of groups represented by the formulas (a): <5 O
CH
3
CH
3 -C K -- O O- (a)
CH
3 CH 3
-
O
0 0 12 or is absent, each of R 1 , R 2 and R 3 is an alkyl group, and n is 1 or 2. A fifth aspect of the invention is directed to a urea-urethane composition which is characterized 5 by comprising a urea-urethane compound and a diluent. A sixth aspect. of the invention is directed to a urea-urethane composition according to the fifth aspect of the invention, wherein the diluent is a urea compound and/or a urethane compound. 10 A seventh aspect of the invention is directed to a urea-urethane composition according to the fifth aspect of the invention, wherein the diluent is a compound obtained by reacting a polyisocyanate compound with a hydroxy compound or an amino compound. 15 An eighth aspect of the invention is directed to a urea-urethane composition obtained by reacting a polyisocyanate compound with a hydroxy compound and an amino compound, which is characterized by comprising 50 wt% or more of a urea-urethane compound having at least 20 one urea group and at least one urethane group in a total number of 2 to 10 in the molecular structure and having a molecular weight of 5,000 or less. A ninth aspect of the invention is directed to a urea-urethane composition according to the eighth 25 aspect of the invention, wherein the hydroxy compound is a phenolic compound. A tenth aspect of the invention is directed to a urea-urethane composition according to the eighth 13 aspect of the invention, wherein the hydroxy compound is an alcohol compound. An eleventh aspect of the invention is directed to a urea-urethane composition according to 5 any one of the eighth to tenth aspects of the invention, wherein the amino compound is an aromatic amino compound. A twelfth aspect of the invention is directed to a urea-urethane composition according to any one of 10 the eighth to eleventh aspects of the invention, wherein the polyisocyanate compound is an aromatic polyisocyanate compound. A thirteenth aspect of the invention is directed to a process for producing a urea-urethane 15 composition which is characterized by reacting a polyisocyanate compound with a hydroxy compound so that the ratio of the number of moles of the polyisocyanate compound to the number of hydroxyl equivalents of the hydroxy compound becomes 100/1 to 1/2, to form one or 20 more urethane groups from some of the isocyanate groups of the polyisocyanate compound, and then adding an amino compound thereto to react the same with the remaining isocyanate group(s) of the polyisocyanate compound to form one or more urea groups. 25 A fourteenth aspect of the invention is directed to a process for producing a urea-urethane composition which is characterized by reacting a polyisocyanate compound with an amino compound so that 14 the ratio of the number of moles of the polyisocyanate compound to the number of amino equivalents of the amino compound becomes 100/1 to 1/2, to form one or more urea groups from some of the isocyanate groups of 5 the polyisocyanate compound, and then adding a hydroxy compound thereto to react the same with the remaining isocyanate group(s) of the polyisocyanate compound to form one or more urethane groups. A fifteenth aspect of the invention is 10 directed to a process for producing a urea-urethane composition according to the thirteenth or fourteenth aspect of the invention, which is characterized by successively carrying out the reaction for forming one or more urethane groups and the reaction for forming 15 one or more urea groups. A sixteenth aspect of the invention is directed to a process for producing a urea-urethane composition which comprises reacting an amino compound with a polyisocyanate adduct obtained by the reaction 20 of a polyisocyanate compound with a hydroxy compound, so that the equivalent ratio of isocyanate group to amino group becomes 2/1 to 1/100, to form one or more urea groups, and then removing the unreacted amino compound. 25 A seventeenth aspect of the invention is directed to a process for producing a urea-urethane composition which comprises reacting a hydroxy compound with a polyisocyanate adduct obtained by the reaction 15 of a polyisocyanate compound with an amino compound, so that the equivalent ratio of isocyanate group to hydroxyl group becomes 2/1 to 1/100, to form one or more urethane groups, and then removing the unreacted 5 hydroxy compound. An eighteenth aspect of the invention is directed to a process for producing a urea-urethane composition according to any one of the thirteenth to seventeenth aspects of the invention, which is 10 characterized by carrying out the reaction for forming one or more urethane groups and/or the reaction for forming one or more urea groups, without a solvent, or carrying out the reaction for forming one or more urethane groups and the reaction for forming one or 15 more urea groups, by the use of the same solvent. A nineteenth aspect of the invention is directed to a process for producing a urea-urethane composition according to any one of the thirteenth to eighteenth aspects of the invention, wherein the 20 reaction for forming one or more urethane groups and/or the reaction for forming one or more urea groups are carried out at a temperature of 0 - 300 0 C. A twentieth aspect of the invention is directed to a process for producing a urea-urethane 25 composition according to any one of the thirteenth to nineteenth aspects of the invention, wherein the reaction for forming one or more urethane groups and/or the reaction for forming one or more urea groups are 16 carried out in the presence of a catalyst. A twenty-first aspect of the invention is directed to a color-producing composition comprising a developer comprising a urea-urethane compound. 5 A twenty-second aspect of the invention is directed to a color-producing composition comprising a developer comprising a urea-urethane compound, and a colorless or light-colored dye precursor. A twenty-third aspect of the invention is 10 directed to a color-producing composition according to the twenty-second aspect of the invention, wherein the colorless or light-colored dye precursor is a leuco dye. A twenty-fourth aspect of the invention is 15 directed to a color-producing composition according to the twenty-first to twenty-third aspects of the invention, wherein said developer is a urea-urethane compound according to any one of the first to fourth aspects of the invention, a urea-urethane composition 20 according to any one of the fifth to twelfth aspects of the invention, or a composition produced by a produc tion process according to any one of the thirteenth to twentieth aspects of the invention. A twenty-fifth aspect of the invention is 25 directed to a color-producing composition according to either of the twenty-third and twenty-fourth aspects of the invention, which is characterized in that the leuco dye is at least one leuco dye selected from triaryl- 17 methane type leuco dyes, fluoran type leuco dyes, fluorene type leuco dyes and diphenylmethane type leuco dyes. A twenty-sixth aspect of the invention is 5 directed to a color-producing composition according to either of the twenty-third and twenty-fourth aspects of the invention, which is characterized in that the leuco dye is a compound represented by the following formula (i): 0 4 Y5 y6 10 wherein both Y 2 and Y 3 are alkyl groups or alkoxyalkyl groups, Y 4 is a hydrogen atom, an alkyl group or an alkoxy group, and each of Y, and Y6 is a hydrogen atom, a halogen atom, an.alkyl group or an alkoxy group. A twenty-seventh aspect of the invention is 15 directed to a color-producing composition according to either of the twenty-third and twenty-fourth aspects of the invention, which is characterized in that the leuco dye is a compound represented by the following formula (j): 18
R
6 R 5 0 R7 0 C= (j) R8 R10
R
9 wherein each of R. and R. is a group represented by the formula (k) or the formula (1): R11 R15 (k) R1 R14
R
13 (wherein each of R 11 through R 15 is a hydrogen atom, a halogen atom, an alkyl group of 1 to 8 carbon atoms, an 5 alkoxy group of 1 to 8 carbon atoms, or -NRR 1 , wherein each of R 1 . and R 17 is an alkyl group of 1 to 8 carbon atoms), or 18 O N N _R19 i (wherein each of R 1 and R 9 is a hydrogen atom, an alkyl group of 1 to 8 carbon atoms, or a phenyl group), and 10 each of R 7 through R 1 . is a hydrogen atom, a halogen atom, an alkyl group of 1 to 8 carbon atoms, an alkoxy group of 1 to 8 carbon atoms, or -NR 20
R
21 wherein each of 19
R
2 0 and R 21 is an alkyl group of 1 to 8 carbon atoms. A twenty-eighth aspect of the invention is directed to a color-producing composition according to any one of the twenty-first to twenty-seventh aspects 5 of the invention, which is characterized in that the melting point of the urea-urethane compound developer is not higher than 500 0 C and not lower than 40 0 C. A twenty-ninth aspect of the invention is directed to a color-producing composition according to 10 any one of the twenty-first to twenty-seventh aspects of the invention, which is characterized in that the urea-urethane compound developer comprises a compound selected from compounds represented by the following general formula (V) or (VI): (V) K~'HK ,g H HK K~ H H H 15 wherein hydrogen atom(s) of each benzene ring may be replaced by an aromatic compound residue, an aliphatic compound residue, a heterocyclic compound residue, a nitro group, a hydroxyl group, a carboxyl group, a nitroso group, a nitrile group, a carbamoyl group, a 20 ureido group, an isocyanate group, a mercapto group, a sulfo group, a sulfamoyl group or a halogen atom, each of the residues may have one or more substituents, y is a group selected from the group consisting of -S0 2 -, -0-, -(S)n-, -(CH 2 )n-, -CO-, -CONH- and any of groups 20 represented by the formulas (a): OO
CH
3
H
3 CH3 OH3 (a) -C --- -O 0- a
CH
3 CH 3 --
OO
0 -0---O
O-
0 or is absent, and n is 1 or 2; and -N--j-* --- HO-(v) H H H H (VI) wherein hydrogen atom(s) of each benzene ring may be 5 replaced by an aromatic compound residue, an aliphatic 21 compound residue, a heterocyclic compound residue, a hydroxyl group, a nitro group, a nitrile group, a carbamoyl group, a sulfamoyl group, a carboxyl group, a nitroso group, an amino group, an oxyamino group, a 5 nitroamino group, a hydrazino group, a ureido group, an isocyanate group, a mercapto group, a sulfo group or a halogen atom, each of the residues may have one or more substituents, 8 is a group selected from the group consisting of -SO 2 -, -0-, -(S)n-, -(CH 2 )n-, -CO-, -CONH-, 10 -NH-, -CH(COOR 1 )-, -C(CF 3 ) 2 - and -CR 2
R
3 - or is absent, each of R 1 , R 2 and R 3 is an alkyl group, and n is 1 or 2. A thirtieth aspect of the invention is directed to a color-producing composition according to any one of the twenty-first to twenty-seventh aspects 15 of the invention, which is characterized in that the urea-urethane compound developer comprises a compound selected from compounds represented by the following structural formulas (XX) and (XXI): 0 /-~\ 0 H3C N -N () -N CH3 O NH HN. O d 0 0 0
(XX)
22 (XXI) CCH -O
O-C
O\ NH HN. 0 NH NH 0 0 A thirty-first aspect of the invention is directed to a color-producing composition according to any one of the twenty-first to thirtieth aspects of the 5 invention, which further comprises a heat-meltable material. A thirty-second aspect of the invention is directed to a color-producing composition according to the thirty-first aspect of the invention, which is 10 characterized in that the heat-meltable material is at least one compound selected from Q-naphthylbenzyl ether, p-benzylbiphenyl, 1,2-di(m-methylphenoxy)ethane, di-p-methylbenzyl oxalate, 1, 2-diphenoxymethylbenzene, m-terphenyl and stearamide. 15 A thirty-third aspect of the invention is directed to a color-producing composition according to the thirty-first aspect of the invention, wherein the heat-meltable material is that represented by the following structural formula (XVIII): 20 0-y I-
(XVIII)
23 wherein Y is any of -SO 2 -, -(S)n-, -0-, -CO-, -CH 2 -, -CH (C 6
H
5 ) -, -C (CH 3 ) 2-1 -COCO-, -C03- -COCH 2 CO-, -COOCH 2 -, -CONH-, -OCH 2 - and -NH-, n is 1 or 2, and hydrogen atom(s) of each benzene ring may be replaced by a 5 halogen atom, a hydroxyl group, a nitro group, a nitroso group, a nitrile group, an isocyanate group, an isothiocyanate group, a mercapto group, a sulfamoyl group, a sulfonic acid group, an amino group, an aromatic compound residue, an aliphatic compound 10 residue or a heterocyclic compound residue. A thirty-fourth aspect of the invention is directed to a color-producing composition according to the thirty-third aspect of the invention, wherein the heat-meltable material is that represented by the 15 following structural formula (XIX): 0 (XIX) 0 wherein hydrogen atom(s) of each benzene ring may be replaced by a halogen atom, a hydroxyl group, a nitro group, a nitroso group, a nitrile group, an isocyanate 20 group, an isothiocyanate group, a mercapto group, a sulfamoyl group, a sulfonic acid group, an amino group, an aromatic compound residue, an aliphatic compound residue or a heterocyclic compound residue. A thirty-fifth aspect of the invention is 25 directed to a color-producing composition according to 24 any one of the twenty-first to thirty-fourth aspects of the invention, which further comprises an isocyanate compound. A thirty-sixth aspect of the invention is 5 directed to a color-producing composition according to any one of the twenty-first to thirty-fourth aspects of the invention, which further comprises an isocyanate compound and an imino compound. A thirty-seventh aspect of the invention is 10 directed to a color-producing composition according to any one of the twenty-first to thirty-sixth aspects of the invention, which further comprises an amino compound. A thirty-eighth aspect of the invention is 15 directed to a color-producing composition according to any one of the twenty-first to thirty-seventh aspects of the invention, wherein the developer further comprises an acidic developer. A thirty-ninth aspect of the invention is 20 directed to a color-producing composition according to the thirty-eighth aspect of the invention, which is characterized in that the acidic developer is at least one developer selected from 2,2-bis(4-hydroxyphenyl) propane, 4-isopropyloxyphenyl-4'-hydroxyphenylsulfone, 25 bis(3-ally-4-hydroxyphenyl)sulfone, 2,4'-dihydroxy diphenylsulfone and 4,4'-[oxybis(ethyleneoxy-p phenylenesulfonyl)]diphenol. A fortieth aspect of the invention is 25 directed to a color-producing composition according to any one of the twenty-first to thirty-ninth aspects of the invention, which further comprises a fluorescent dye. 5 A forty-first aspect of the invention is directed to a color-producing composition according to any one of the twenty-first to fortieth aspects of the invention, which further comprises a shelf-stability imparting agent. 10 A forty-second aspect of the invention is directed to a recording material comprising a substrate and a color-producing layer formed thereon, said color producing layer comprising a urea-urethane compound according to any one of the first to fourth aspects of 15 the invention, a urea-urethane composition according to any one of the fifth to twelfth aspects of the invention, or a color-producing composition according to any one of the twenty-first to forty-first aspects of the invention. 20 A forty-third aspect of the invention is directed to a recording material according to the forty-second aspect of the invention, which is characterized in that a protective layer for the color producing layer is formed on the color-producing layer. 25 A forty-fourth aspect of the invention is directed to a recording material according to the forty-third aspect of the invention, which is characterized in that the protective layer comprises a 26 water-soluble polymer. A forty-fifth aspect of the invention is directed to a recording material according to either of the forty-third and forty-fourth aspects of the 5 invention, which is characterized in that the protec tive layer comprises an inorganic pigment and/or an organic pigment. A forty-sixth aspect of the invention is directed to a recording material according to any one 10 of the forty-third to forty-fifth aspects of the invention, which is characterized in that the protec tive layer comprises a lubricant. A forty-seventh aspect of the invention is directed to a recording material according to the 15 forty-second aspect of the invention, which is characterized in that an intermediate layer is formed on the substrate and that the color-producing layer is formed on said intermediate layer. A forty-eighth aspect of the invention is 20 directed to a recording material according to the forty-seventh aspect of the invention, which is characterized in that the intermediate layer comprises a water-soluble polymer. A forty-ninth aspect of the invention is 25 directed to a recording material according to either of the forty-seventh and forty-eighth aspects of the invention, which is characterized in that the inter mediate layer comprises an inorganic pigment and/or an 27 organic pigment. A fiftieth aspect of the invention is directed to a recording material according to the forty-second aspect of the invention, which is 5 characterized in that a back coating layer is formed on the substrate on the side reverse to the side having the color-producing layer formed thereon. A fifty-first aspect of the invention is directed to a recording material according to the 10 fiftieth aspect of the invention, which is character ized in that the back coating layer comprises a water soluble polymer. A fifty-second aspect of the invention is directed to a recording material according to either of 15 the fiftieth and fifty-first aspects of the invention, which is characterized in that the back coating layer comprises an inorganic pigment and/or an organic pigment. A fifty-third aspect of the invention is 20 directed to a recording material according to any one of the forty-second to fifty-second aspects of the invention, which is characterized by using at least one compound selected from water-soluble polymers and anionic surfactants, as a dispersing agent for the 25 urea-urethane compound. A fifty-fourth aspect of the invention is directed to a recording material according to any one of the forty-second to fifty-second aspects of the 28 invention, which is characterized by using at least one compound selected from poly(vinyl alcohol)s, modified poly(vinyl alcohol)s, methyl cellulose, hydroxypropyl methyl cellulose, condensed sodium naphthalene 5 sulfonate, polycarboxylic acid ammonium salts, water soluble low-molecular weight copolymers, and sodium 2 ethylhexylsulfosuccinate, as a dispersing agent for the urea-urethane compound. A fifty-fifth aspect of the invention is 10 directed to a recording material according to any one of the forty-second to fifty-fourth aspects of the invention, which is characterized by using at least one compound selected from water-soluble polymers, nonionic surfactants and anionic surfactants, as a dispersing 15 agent for a dye precursor. A fifty-sixth aspect of the invention is directed to a recording material according to any one of the forty-second to fifty-fourth aspects of the invention, which is characterized by using at least one 20 compound selected from methyl cellulose, hydroxy propylmethyl cellulose, polyethylene glycol fatty acid esters, polyoxyethylene alkyl ether sulfates and sodium 2-ethylhexylsulfosuccinate, as a dispersing agent for a dye precursor. 25 A fifty-seventh aspect of the invention is directed to a recording material according to any one of the forty-second to fifty-sixth aspects of the invention, which is a heat-sensitive recording 29 material. A fifty-eighth aspect of the invention is directed to a heat-sensitive recording material accord ing to the fifty-seventh aspect of the invention, which 5 is characterized in that the average particle size of the urea-urethane compound is not more than 5 pm and not less than 0.05 pm. A fifty-ninth aspect of the invention is directed to a heat-sensitive recording material accord 10 ing to the fifty-seventh and fifty-eighth aspects of the invention, which is characterized in that a liquid temperature at grinding of the urea-urethane compound is 60 0 C or lower. A sixtieth aspect of the invention is 15 directed to a heat-sensitive recording material accord ing to any one of the fifty-seventh to fifty-ninth aspects of the invention, which is characterized in that a pH at grinding of the urea-urethane compound is 5 to 10. 20 A sixty-first aspect of the invention is directed to a heat-sensitive recording material accord ing to any one of the fifty-seventh to sixtieth aspects of the invention, which is characterized by using at least one compound selected from water-soluble polymers 25 and anionic surfactants, as a dispersing agent for a heat-meltable material. A sixty-second aspect of the invention is directed to a heat-sensitive recording material accord- 30 ing to any one of the fifty-seventh to sixtieth aspects of the invention, which is characterized by using at least one compound selected from poly(vinyl alcohol)s, modified poly(vinyl alcohol)s, methyl cellulose, 5 hydroxypropylmethyl cellulose, condensed sodium naphthalenesulfonate, polycarboxylic acid ammonium salts, water-soluble low-molecular weight copolymers, and sodium 2-ethylhexylsulfosuccinate, as a dispersing agent for a heat-meltable material. 10 A sixty-third aspect of the invention is directed to a heat-sensitive recording material accord ing to any one of the fifty-seventh to sixty-second aspects of the invention, which is characterized in that the urea-urethane compound and a heat-meltable 15 material are finely ground together. A sixty-fourth aspect of the invention is directed to a heat-sensitive recording material accord ing to any one of the fifty-seventh to sixty-third aspects of the invention, which is characterized in 20 that the pH of the substrate surface to be coated with the heat-sensitive recording layer of the heat sensitive recording material is 3 to 9. A sixty-fifth aspect of the invention is directed to a process for producing a heat-sensitive 25 recording material according to any one of the fifty seventh to sixty-fourth aspects of the invention, which is characterized by applying on the substrate a heat sensitive coating liquid of pH 5 to 12 for forming the 31 heat-sensitive recording layer of the heat-sensitive recording material. A sixty-sixth aspect of the invention is directed to a recording material according to the 5 forty-second aspect of the invention, which is a heat sensitive magnetic recording material. A sixty-seventh aspect of the invention is directed to a heat-sensitive magnetic recording material according to the sixty-sixth aspect of the 10 invention, which is characterized in that a heat sensitive recording layer comprising a urea-urethane compound developer is formed on one side of the substrate, and a magnetic recording layer on the other side. 15 A sixty-eighth aspect of the invention is directed to a railroad ticket that is a heat-sensitive magnetic recording material according to the sixty sixth or sixty-seventh aspect of the invention. A sixty-ninth aspect of the invention is 20 directed to a ticket that is a heat-sensitive magnetic recording material according to the sixty-sixth or sixty-seventh aspect of the invention. A seventieth aspect of the invention is directed to a recording material according to the 25 forty-second aspect of the invention, which is a label for heat-sensitive recording. A seventy-first aspect of the invention is directed to a label for heat-sensitive recording 32 according to the seventieth aspect of the invention, which is characterized in that a heat-sensitive recording layer comprising a urea-urethane compound developer is formed on one side of the substrate, and 5 an adhesive layer on the other side. A seventy-second aspect of the invention is directed to a label for heat-sensitive recording according to the seventy-first aspect of the invention, which is characterized in that a back coating layer is 10 formed between the adhesive layer and the substrate. A seventy-third aspect of the invention is directed to a label for heat-sensitive recording according to either of the seventy-first and seventy second aspects of the invention, which is characterized 15 in that an intermediate layer is formed between the heat-sensitive recording layer and the substrate. A seventy-fourth aspect of the invention is directed to a label for heat-sensitive recording according to any one of the seventy-first to seventy 20 third aspects of the invention, which is characterized in that a protective layer is formed on the heat sensitive recording layer. A seventy-fifth aspect of the invention is directed to a recording material according to the 25 forty-second aspect of the invention, which is a multicolor heat-sensitive recording material. A seventy-sixth aspect of the invention is directed to a multicolor heat-sensitive recording 33 material according to the seventy-fifth aspect of the invention, wherein at least two heat-sensitive record ing layers are formed on one side of the substrate, said recording material being characterized in that at 5 least one of said heat-sensitive recording layers comprises a urea-urethane compound developer. A seventy-seventh aspect of the invention is directed to a multicolor heat-sensitive recording material according to the seventy-sixth aspect of the 10 invention, which is characterized in that an inter mediate layer is formed between the heat-sensitive recording layers. A seventy-eighth aspect of the invention is directed to a multicolor heat-sensitive recording 15 material characterized by comprising a substrate and two heat-sensitive recording layers laminated on one side of the substrate which have different color development temperatures, respectively, and undergo color development in different color tones, respec 20 tively, the upper heat-sensitive recording layer comprising either an agent used both as developer and tone reducer, or a reversible developer, and the lower heat-sensitive recording layer comprising a urea urethane compound developer. 25 A seventy-ninth aspect of the invention is directed to a multicolor heat-sensitive recording material according to the seventy-eighth aspect of the invention, which is characterized in that, of the two 34 heat-sensitive recording layers, the upper layer is a low-temperature color-producing layer capable of undergoing color development at a low temperature and undergoing achromatization at a high temperature, and 5 the lower layer is a high-temperature color-producing layer capable of undergoing color development at a high temperature. An eightieth aspect of the invention is directed to an article for laser marking characterized 10 by having on the surface a heat-sensitive recording layer comprising a urea-urethane compound developer. An eighty-first aspect of the invention is directed to an article for laser marking characterized by having on the surface a heat-sensitive recording 15 layer comprising a colorless or light-colored dye precursor, a urea-urethane compound developer and a recording sensitivity improving agent. An eighty-second aspect of the invention is directed to an article for laser marking according to 20 either of the eightieth and eighty-first aspects of the invention, which is characterized by having on the heat-sensitive recording layer a protective layer comprising an aqueous binder having a glass transition point of 20 - 80 0 C. 25 An eighty-third aspect of the invention is directed to an article for laser marking according to the eighty-first aspect of the invention, wherein the recording sensitivity improving agent is at least one 35 compound selected from aluminum hydroxide, muscovite, wollastonite and kaolin. An eighty-fourth aspect of the invention is directed to an article for laser marking according to 5 any one of the eightieth to eighty-third aspects of the invention, which is any of labels, packaging materials and containers. An eighty-fifth aspect of the invention is directed to a process for producing an article for 10 laser marking which is characterized by applying on a substrate a color-producing marking composition comprising a urea-urethane compound developer, and drying the thus treated substrate. An eighty-sixth aspect of the invention is 15 directed to a process for producing an article for laser marking which is characterized by applying on a substrate a color-producing marking composition comprising a colorless or light-colored dye precursor, a urea-urethane compound developer and a recording 20 sensitivity improving agent, and drying the thus treated substrate. An eighty-seventh aspect of the invention is directed to a method for marking an article which is characterized by irradiating the heat-sensitive 25 recording layer of an article for laser marking according to any one of the eightieth to eighty-fourth aspects of the invention, with laser beams. An eighty-eighth aspect of the invention is 36 directed to a color-producing marking composition characterized by comprising a urea-urethane compound developer. An eighty-ninth aspect of the invention is 5 directed to a color-producing marking composition characterized by comprising a colorless or light colored dye precursor, a urea-urethane compound developer and a recording sensitivity improving agent. BEST MODE FOR CARRYING OUT THE INVENTION 10 The present invention is explained below in detail. Each of the urea-urethane compounds of the first to fourth aspects of the present invention has both at least one urea group and at least one urethane 15 group. In the urea-urethane compounds of the first to fourth aspects of the present invention, an aliphatic compound residue is bonded to the terminal oxygen atom of the urethane group. Therefore, the 20 urea-urethane compounds can be obtained as compounds excellent in physical and chemical stability, in particular, heat stability. Moreover, the urea urethane compounds can be obtained by using relatively inexpensive materials. 25 In addition, a starting alcohol compound for the aliphatic compound residue bonded to the terminal oxygen atom of the urethane group can easily be removed 37 even if it remains unreacted in the synthetic reaction of the urea-urethane compound. Therefore, the urea urethane compounds can be obtained with a high purity. Preferable forms at the ends of the urea 5 group vary depending on the molecular size of the urea urethane compound. In the urea-urethane compound of the formula (c), each end of the urea group should be bonded to an aromatic compound residue. The aromatic compound residue is preferably an aromatic ring shown 10 in the formula (d). In the urea-urethane compounds of the formulas (e) and (f) having a relatively large molecular size, a group at each end of the urea group is, for example, as follows: in the formula (e), the group at each end may be any of an aromatic compound 15 residue, a heterocyclic compound residue and an aliphatic compound residue, and in the formula (f), the group at each end may be either an aromatic compound residue or a heterocyclic compound residue. In both the formulas (e) and (f), the group at each end of the 20 urea group is preferably an aromatic compound residue. The urea group and the urethane group are adjacent to each other through at least one compound residue (such a structure portion is hereinafter referred to as a urea-urethane structure portion). It is preferable 25 that only one compound residue be present between the urea group and the urethane group. In addition, this residue is preferably an aromatic ring. Although a concrete mechanism by which the 38 urea-urethane compounds of the first to fourth aspects of the present invention function as a developer is unknown, it is conjectured that the function is due to the interaction between the urea group and the urethane 5 group in the urea-urethane structure portion. The number of urea-urethane structure portions is two or more in the formulas (e) and (f). On the other hand, the number of urea-urethane structure portions is one in some cases in the urea-urethane compound of the 10 formula (c) or (d). In this case, the following is conjectured: in the urea-urethane compound of the formula (c) or (d), a residue to be bonded to each end of the urea group is limited to the most preferable residue, i.e., an aromatic compound residue in order to 15 enable the compound to function as a developer to a cetain extent; on the other hand, in the formulas (e) and (f), a residue to be bonded to each end of the urethane group need not always be an aromatic compound residue. 20 It is sufficient that the number of urea urethane structure portions present in the molecule be 1 to 10, preferably 1 to 5, more preferably 2 to 4. The urea-urethane compound may have in the molecule one or more other urea groups and urethane 25 groups in addition to the urea-urethane structure portion(s). The term "aliphatic" used in the case of the first to fourth aspects of the present invention 39 includes the term "alicyclic". The term "aliphatic compound residue" used in the case of the first to fourth aspects of the present invention means a residue bonded by the carbon atom of 5 the aliphatic hydrocarbon portion in the residue. The term "aromatic compound residue" used therein means a residue bonded by the carbon atom of the aromatic ring such as benzene ring in the residue. The term "heterocyclic compound residue" used therein means a 10 residue bonded by a carbon atom forming the hetero cyclic ring in the residue. Preferable examples of the substituents of the aliphatic compound residue, the heterocyclic compound residue and the aromatic compound residue are 15 alkyl groups, cycloalkyl groups, phenyl group, amide group, alkoxyl groups, nitro group, nitrile group, halogen atoms, formyl group, dialkylamino groups, toluenesulfonyl group and methanesulfonyl group. When it is considered that the urea-urethane 20 compounds of the first to fourth aspects of the present invention are used as a developer or in a heat sensitive recording material, the total number of one or more aliphatic urethane groups and one or more urea groups, which are present in the molecular structure of 25 each of the urea-urethane compounds of the first to fourth aspects of the present invention is not more than 11 and not less than 2, preferably not more than 11 and not less than 3, more preferably not more than 40 11 and not less than 4. The ratio of the urethane group(s) to the urea group(s) is preferably 1 : 3 to 3 : 1, more preferably 1 : 2 to 2 : 1, most preferably 1 : 1. The molecular weight of the urea-urethane 5 compounds is 5,000 or less, preferably 2,000 or less. In a heat-sensitive recording material, a compound having a melting point is preferably used. The melting point or the urea-urethane compounds of the first to fourth aspects of the present invention ranges 10 preferably from 400C to 5000C, more preferably from 60'C to 3000C, most preferably from 600C to 2500C. A process for synthesizing each of the urea urethane compounds of the first to fourth aspects of the present invention is not particularly limited. A 15 process in which the urea-urethane compound is synthesized by the reaction of an isocyanate compound with an alcohol compound and an amine compound is preferable because of its ease. A process for producing the urea-urethane 20 compound of the formula (c) of the first aspect of the present invention is not limited. This compound can be obtained, for example, by reacting an alcohol compound of the following formula (m) with an isocyanate compound of the following formula (n) and an amine 25 compound of the following formula (o) according to, for example, the reaction formula (A') or (B') shown below: R -OH (M) wherein R is an aliphatic compound residue which may 41 have one or more substituents;
OCN-A
1 -NCO (n) wherein A, is an aromatic compound residue which may have one or more substituents; and
A
2
-NH
2 (o) wherein A 2 is an aromatic compound residue which may 5 have one or more substituents. 0 Il R-OH + OCN-A 1 -NCO -P R-0 N-A 1 -NCO (A) H o 0 0 C0C C R-0C N-A 1 -NCO + A 2
-NH
2 + R-O0 N-A 1 -N N-A2 H H H H 0
A
2
-NH
2 + OCN-A 1 -NCO -- + OCN-A-N -A2 H (B') 0 0 0 R-OH + OCN-A 1
-
6 ' N-A 2 - R--O N-A--N N-A 2 H H H H H A process for producing the urea-urethane compound of the formula (d) of the second aspect of the present invention is not particularly limited. This compound can be obtained, for example, by reacting an 10 alcohol compound of the formula (m) with an isocyanate compound of the following formula (p) and an amine compound of the following formula (q) according to, for example, the reaction formula (C') or (D') shown below: 42 OCN -NCO (p) wherein hydrogen atom(s) of the benzene ring may be replaced by an aromatic compound residue, an aliphatic compound residue, a heterocyclic compound residue, a hydroxyl group, a nitro group, a nitrile group, a 5 carbamoyl group, a sulfamoyl group, a carboxyl group, a nitroso group, an amino group, an oxyamino group, a nitroamino group, a hydrazino group, a ureido group, an isocyanate group, a mercapto group, a sulfo group or a halogen atom, and each of the residues may have one or 10 more substituents; and
NH
2 (q) wherein hydrogen atom(s) of the benzene ring may be replaced by an aromatic compound residue, an aliphatic compound residue or a heterocyclic compound residue, and each of the residues may have one or more 15 substituents. 0 OCN4 NCO Nj C R-OH + OCN R-0 NCO (C') 0 0 0 R-0 Nb~C +-NH 2 R-0~ 43 0 -- NH2 + OCN+ -NCO - OCN N H (D') 0 0 0 R-OH + OCN - + R-O K~H H A process for producing the urea-urethane compound of the formula (e) of the third aspect of the present invention is not limited. This compound can be obtained, for example, by reacting an alcohol compound 5 of the general formula (m) with an isocyanate compound of the following general formula (r) and an amine compound of the following general formula (s) according to, for example, the reaction formula (E') or (F') shown below: 10 OCN-Y-NCO (r) wherein Y is an aromatic compound residue, a hetero cyclic compound residue or an aliphatic compound residue, and each of the residues may have one or more substituents; and 15 cXl iNH 2 ) (S) wherein at is an aromatic, aliphatic or heterocyclic compound residue having a valence of 2 or more, n is an integer of 2 or more, and each of the residues may have one or more substituents.
44 0 R-OH + OCN-Y-NCO--+- R-O' N-Y-NCO H (E') F 0 0- 0 n R-O N-Y-NCO + a NH 2 ) + R-0 'N-Y-N' 'N- a 1 H n H H H n L .fO NH 2) n + OCN-Y-NCO - OCN-Y-N/ N- a 1 L H i n(F') 0 0a n R-H + CN-Y-N/8' ___(x -0-R08N-Y-N/'-N -N a 1 H H H H
.
n n-n A process for producing the urea-urethane compound of the formula (f) of the third aspect of the present invention is not limited. This compound can be obtained, for example, by reacting an amine compound of 5 the following general formula (t) with an isocyanate compound of the general formula (r) and an alcohol compound of the following general formula (u) according to, for example, the reaction formula (G') or (H') shown below: 10
Z-NH
2 (t) wherein Zi is is an aromatic compound residue or a heterocyclic compound residue, and each of the residues may have one or more substituents; and 01 OH n (u) 45 wherein 01 is an aliphatic compound residue which has a valence of 2 or more and may have one or more substituents, and n is an integer of 2 or more. 0
Z
1
-NH
2 + OCN-Y-NCO - OCN-Y-N' N-Z 1 H H (G') 0 0 0 ni OCN-Y- Z1 + 010H J 6- -O ' Y -Z1 n 0 0 OH + n' OCN-Y-NCO +40- O-O Y-NCO (H') n 0 1 1- - >l-Y-NCO + n Z 1
-NH
2 -+ -- O' 0 'Y- 6 -Z1j n n A process for producing the urea-urethane 5 compound of the formula (g) of the fourth aspect of the present invention is not limited. This compound can be obtained, for example, by reacting an alcohol compound of the formula (u) with an isocyanate compound of the formula (p) and an amine compound of the formula (q) 10 according to, for example, the reaction formula (i') or (J') shown below: 46 0 4~~~ ~ OH+nOC-" 1 OH +in OCN- -NCO P p--O -- -NCO1 (i') 0 0 0 fplr{0-ON - -NCO + n -H Cr -O' - 0 OCN- NCO -' OCN 6N N- A% COH H (J') 0 0 0 n OCN- NN -> +N p-140H-I-p -' '-N N-Q 0- n SH H !0 Hn A process for producing the urea-urethane compound of the formula (h) of the fourth aspect of the present invention is not limited. This compound can be obtained, for example, by reacting an amine compound of 5 the following formula (XVII) with an isocyanate compound of the formula (p) and an alcohol compound of the general formula (m) according to, for example, the reaction formula (K') or (L') shown below:
NH
2 71
NH
2 (XVII) 10 wherein hydrogen atom(s) of each benzene ring may be replaced by an aromatic compound residue, an aliphatic compound residue, a heterocyclic compound residue, a nitro group, a hydroxyl group, a carboxyl group, a 47 nitroso group, a nitrile group, a carbamoyl group, a ureido group, an isocyanate group, a mercapto group, a sulfo group, a sulfamoyl group or a halogen atom, each of the residues may have one or more substituents, y 1 is 5 a group selected from the group consisting of -S0 2 -, -O-, -(S)n-, -(CH2)n-, -CO-, -CONH-, -NH-, -CH(COOR1)-, -C(CF3) 2 -, -CR 2
R
3 - and any of groups represented by the formulas (a): 48
CH
3
CH
3 -c -- 0 -- (a)
CH
3
CH
3 0-000 0 or is absent, each of R 1 , R 2 and R 3 is an alkyl group, and n is 1 or 2.
49 0 R-OH + OCN-j- -NCO - R-O N NCO H (K') O 2 R-O NK; G-NCO + H 2 N-- -- y& -NH 2 H 0 0 09 + R-0 N N N Y1 N N- -N/ 0-R H K H HKS K H H9 H H2N-- Y1 -NH2 + 2 OCN-- -NCO (L') 0 0 -O - OCN - N N-- Y- - N N -+NCO HH H 0 0 OCNI Nj- -NCO + 2R-OH H HK~ H HK 0 0 0 0 +P R-O N N/ N 1- N N N 0-R HK H H k H HK H The compounds of the formulas (m) to (u) which can be used for synthesis of the urea-urethane compounds of the above formulas (c) to (h) are explained below in further detail. 5 As the alcohol compound of the general formula (m), any alcohol compound may be used so long 50 as it has one or more OH groups bonded to one or more carbon atoms, respectively, of an aliphatic compound. Examples of the alcohol compound are the alcohols described in Solvent Handbook, Kodansha Scientific Co., 5 Ltd., the ninth impression (1989), pp. 327-420 and pp. 772-817. The alcohol compound includes, for example, aliphatic alcohols such as methanol, ethanol, propanol, isopropanol, n-butanol, isobutanol, sec-butanol, tert butanol, pentanol, cyclopentanol, tert-amyl alcohol, 2 10 pentanol, isoamyl alcohol, hexanol, 3-hexanol, cyclohexanol, cyclohexylmethanol, 4-methyl-2-pentanol, heptanol, isoheptanol, octanol, 2-ethyl-l-hexanol, capryl alcohol, nonyl alcohol, isononyl alcohol, decanol, undecyl alcohol, dodecyl alcohol, tridecyl 15 alcohol, tetradecyl alcohol, hexadecyl alcohol, octadecyl alcohol, isostearyl alcohol, etc.; unsaturated aliphatic alcohols such as ally alcohol, 2 methyl-2-propen-l-ol, crotyl alcohol, propargyl alcohol, etc.; aliphatic alcohols having an aromatic 20 compound residue bonded thereto, such as benzyl alcohol, cinnamyl alcohol, etc.; aliphatic alcohols having a heterocyclic compound residue bonded thereto, such as 2-pyridinemethanol, 3-pyridinemethanol, 4 pyridinemethanol, furfuryl alcohol, etc.; halogenated 25 aliphatic alcohols such as 2-chloroethanol, 1-chloro-3 hydroxypropane, etc.; glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene 51 glycol monoisopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monoisobutyl ether, ethylene glycol monohexyl ether, ethylene glycol monophenyl ether, diethylene glycol monomethyl ether, diethylene 5 glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monobutyl ether, diethylene glycol monoisobutyl ether, diethylene glycol monohexyl ether, diethylene glycol monophenyl ether, propylene glycol 10 monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monoisopropyl ether, propylene glycol monobutyl ether, propylene glycol monoisobutyl ether, propylene glycol monophenyl ether, dipropylene glycol monomethyl ether, 15 dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monoisopropyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monoisobutyl ether, dipropylene glycol monophenyl ether, etc.; diols such as ethylene glycol, 20 diethylene glycol, triethylene glycol, 1,3-propanediol, 1,2-propanediol, propylene glycol, dipropylene glycol, tripropylene glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, hexylene glycol, 1,9-nonanediol, neopentyl glycol, methylpentanediol, etc.; aliphatic 25 polyols such as glycerin, castor oil, trimethylol propane, trimethylolethane, hexanetriol, pentaery thritol, a-methyl glucoside, sorbitol, sucrose, etc.; polyols such as polyethylene glycols, polypropylene 52 glycols, polytetramethylene glycols, adipate-derived polyols, epoxy-modified polyols, polyether ester polyols, polycarbonate polyols, polycaprolactone diols, amine-modified polyols, polyether polyols obtained by 5 adding one of or a mixture of two or more of alkylene oxides (e.g. ethylene oxide and propylene oxide) to one of or a mixture of two or more of polyhydric alcohols (glycerin and propylene glycol), acryl polyols, fluorinated polyols, polybutadiene polyols, polyhydroxy 10 polyols, castor-oil-derived polyols, polymer polyols, halogen-containing polyols, phosphorus-containing polyols, etc.; and alkanolamines such as N,N-dialkyl ethanolamines, N,N-dialkylisopropanolamines, N alkyldiethanolamines, N-alkyldiisopropanolamines, 15 triethanolamine, triisopropanolamine, N,N,N',N' tetrakis(2-hydroxyethyl)ethylenediamine, N,N,N',N' tetrakis(2-hydroxypropyl)ethylenediamine, etc. Of the above-exemplified alcohol compounds, monoalcohols having one OH group are preferable, and 20 aliphatic alcohols and glycol ethers, which have 10 or less carbon atoms are more preferable. The isocyanate compound of the formula (n) is not particularly limited so long as it is an aromatic isocyanate having two or more isocyanate groups bonded 25 to carbon atoms, respectively. The isocyanate compound includes, for example, p-phenylene diisocyanate, m phenylene diisocyanate, o-phenylene diisocyanate, 2,5 dimethoxybenzene-1,4-diisocyanate, 2,4-toluene 53 diisocyanate, 2,6-toluene diisocyanate, diphenylmethane diisocyanate, o-tolidine diisocyanate, diphenyl ether diisocyanate, 1,5-naphthylene diisocyanate, dianisidine diisocyanate, 3,3'-dimethyl-4,4'-diphenylmethane 5 diisocyanate, triphenylmethane triisocyanate, tris(4 phenylisocyanate) thiophosphate, 4,4',4"-triisocyanato 2,5-dimethoxytriphenylamine and 4,4',4"-triisocyanato triphenylamine. As the isocyanate compound of the formula (n), there may also be used diisocyanate dimers 10 such as N,N'-(4,4'-dimethyl-3,3'-diphenyldiisocyanato) urethodione (Desmodule TT, a trade name), a toluene diisocyanate dimer; and diisocyanate trimers such as 4,4',4"-trimethyl-3,3',3"-triisocyanato-2,4,6 triphenylcyanurate. There may also be used water 15 adduct isocyanates of toluene diisocyanate, diphenyl methane diisocyanate and the like, such as 1,3-bis(3 isocyanato-4-methylphenyl)urea; polyol adducts such as trimethylolpropane adducts of toluene diisocyanate (Desmodule L and Coronate L, trade names); and amine 20 adducts. There may also be used compounds having two or more isocyanate groups, among the isocyanate compounds and isocyanate adduct compounds described in the specification of JP-A-10-76757 and the specifica tion of JP-A-10-95171 (the contents of these references 25 are hereby incorporated herein by reference). Of the above-exemplified isocyanate compounds, aromatic isocyanates having isocyanate groups bonded to a benzene ring are preferable. More 54 preferable are p-phenylene diisocyanate, m-phenylene diisocyanate, o-phenylene diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, diphenylmethane diisocyanate, o-tolidine diisocyanate, diphenyl ether 5 diisocyanate, 1,5-naphthylene diisocyanate, triphenyl methane triisocyanate, N,N'-(4,4'-dimethyl-3,3' diphenyldiisocyanato)urethodione (Desmodule TT, a trade name), 4,4',4"-trimethyl-3,3',3"-triisocyanato-2,4,6 triphenylcyanurate, 1,3-bis(3-isocyanato-4-methyl 10 phenyl)urea, and trimethylolpropane adducts of toluene diisocyanate (Desmodule L and Coronate L, trade names). Especially preferable examples of the isocyanate compound of the formula (n) are toluene diisocyanates. Of the toluene diisocyanates, 2.4-toluene diisocyanate 15 is preferable. Besides 2.4-toluene diisocyanate, mixtures of 2.4-toluene diisocyanate and 2,6-toluene diisocyanate are generally on the market and available at a low price and may also be used as the isocyanate compound of the formula (n). 20 As the amine compound of the general formula (o), there are mentioned, for example, aromatic amines such as aniline, o-toluidine, m-toluidine, p-toluidine, o-anisidine, p-anisidine, p-phenetidine, N,N-dimethyl p-phenylenediamine, N,N-diethyl-p-phenylenediamine, 25 2,4-dimethoxyaniline, 2,5-dimethoxyaniline, 3,4 dimethoxyaniline, p-aminoacetanilide, p-aminobenzoic acid, o-aminophenol, m-aminophenol, p-aminophenol, 2,3 xylidine, 2,4-xylidine, 3,4-xylidine, 2,6-xylidine, 4- 55 aminobenzonitrile, anthranilic acid, p-cresidine, 2,5 dichloroaniline, 2,6-dichloroaniline, 3,4-dichloro aniline, 3,5-dichloroaniline, 2,4,5-trichloroaniline, a-naphthylamine, aminoanthracene, o-ethylaniline, o 5 chloroaniline, m-chloroaniline, p-chloroaniline, N methylaniline, N-ethylaniline, N-propylaniline, N butylaniline, acetoacetic acid anilide, trimethyl phenylammonium bromide, 4,4'-diamino-3,3'-diethyl diphenylmethane, 4,4'-diaminobenzanilide, 3,5 10 diaminochlorobenzene, diaminodiphenyl ether, 3,3' dichloro-4,4'-diaminodiphenylmethane, 3,3'-dimethyl 4,4'-diaminodiphenylmethane, tolidine base, o phenylenediamine, m-phenylenediamine, p-phenylene diamine, 2-chloro-p-phenylenediamine, dianisidine, 15 methyl p-aminobenzoate, ethyl p-aminobenzoate, n-propyl p-aminobenzoate, isopropyl p-aminobenzoate, butyl p aminobenzoate, dodecyl p-aminobenzoate, benzyl p aminobenzoate, o-aminobenzophenone, m-aminoaceto phenone, p-aminoacetophenone, m-aminobenzamide, o 20 aminobenzamide, p-aminobenzamide, p-amino-N-methyl benzamide, 3-amino-4-methylbenzamide, 3-amino-4 methoxybenzamide, 3-amino-4-chlorobenzamide, p- (N phenylcarbamoyl)aniline, p-[N-(4-chlorophenyl) carbamoyllaniline, p-[N-(4-aminophenyl)carbamoyl] 25 aniline, 2-methoxy-5-(N-phenylcarbamoyl)aniline, 2 methoxy-5-[N-(2'-methyl-3'-chlorophenyl)carbamoyl] aniline, 2-methoxy-5-[N-(2'-chlorophenyl)carbamoyl] aniline, 5-acetylamino-2-methoxyaniline, 4-acetylamino- 56 aniline, 4-(N-methyl-N-acetylamino)aniline, 2,5 diethoxy-4-(N-benzoylamino)aniline, 2,5-dimethoxy-4-(N benzoylamino)aniline, 2-methoxy-4-(N-benzoylamino)-5 methylaniline, 4-sulfamoylaniline, 3-sulfamoylaniline, 5 2-(N-ethyl-N-phenylaminosulfonyl)aniline, 4-dimethyl aminosulfonylaniline, 4-diethylaminosulfonylaniline, sulfathiazole, 4-aminodiphenyl sulfone, 2-chloro-5-N phenylsulfamoylaniline, 2-methoxy-5-N,N-diethyl sulfamoylaniline, 2,5-dimethoxy-4-N-phenysulfamoyl 10 aniline, 2 -methoxy-5-benzylsulfonylaniline, 2 phenoxysulfonylaniline, 2-(2'-chlorophenoxy)sulfonyl aniline, 3 -anilinosulfonyl-4-methylaniline, bis[4-(m aminophenoxy)phenyl] sulfone, bis[4-(p-aminophenoxy) phenyl] sulfone, bis[3-methyl-4-(p-aminophenoxy)phenyl] 15 sulfone, 3,3'-dimethoxy-4,4'-diaminobiphenyl, 3,3' dimethyl-4,4'-diaminobiphenyl, 2,2'-dichloro-4,4' diamino-5,5'-dimethoxybiphenyl, 2,2',5,5'-tetrachloro 4,4'-diaminobiphenyl, o-tolidine sulfone, 2,4'-diamino biphenyl, 2,2'-diaminobiphenyl, 4,4'-diaminobiphenyl, 20 2,2'-dichloro-4,4'-diaminobiphenyl, 3,3'-dichloro-4,4' diaminobiphenyl, 2,2'-dimethyl-4,4'-diaminobiphenyl, 4,4'-thiodianiline, 2,2'-dithiodianiline, 4,4' dithiodianiline, 4,4'-diaminodiphenyl ether, 3,3' diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 25 4,4'-diaminodiphenylmethane, 3,4'-diaminodiphenyl methane, bis(3-amino-4-chlorophenyl) sulfone, bis(3,4 diaminophenyl) sulfone, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl 57 sulfone, 3,3'-diaminodiphenylmethane, 4,4-diamino diphenylamine, 4,4'-ethylenedianiline, 4,4'-diamino 2,2'-dimethyldibenzyl, 3,3'-diaminobenzophenone, 4,4' diaminobenzophenone, 1,4-bis(4-aminophenoxy)benzene, 5 1,3-bis(4-aminophenoxy)benzene, 1,3-bis(3-amino phenoxy)benzene, 9,9-bis(4-aminophenyl)fluorene, 2,2 bis(4-aminophenoxyphenyl)propane, 4,4'-bis(4-amino phenoxy)diphenyl, 3,3',4,4'-tetraaminodiphenyl ether, 3,3',4,4'-tetraaminodiphenyl sulfone, 3,3',4,4' 10 tetraaminobenzophenone, 3-aminobenzonitrile, 4 phenoxyaniline, 3-phenoxyaniline, 4,4'-methylenebis-o toluidine, 4,4'-(p-phenyleneisopropylidene)-bis-(2,6 xylidine), o-chloro-p-nitroaniline, o-nitro-p chloroaniline, 2,6-dichloro-4-nitroaniline, 5-chloro-2 15 nitroaniline, 2-amino-4-chlorophenol, o-nitroaniline, m-nitroaniline, p-nitroaniline, 2-methyl-4 nitroaniline, m-nitro-p-toluidine, 2-amino-5 nitrobenzonitrile, Metol, 2,4-diaminophenol, N-(0 hydroxyethyl)-o-aminophenol sulfate, sulfanilic acid, 20 metanilic acid, 4B acid, C acid, 2B acid, p-fluoro aniline, o-fluoroaniline, 3-chloro-4-fluoroaniline, 2,4-difluoroaniline, 2,3,4-trifluoroaniline, m aminobenzotrifluoride, m-toluylenediamine, 2 aminothiophenol, 2-amino-3-bromo-5-nitrobenzonitrile, 25 diphenylamine, p-aminodiphenylamine, octylated diphenylamine, 2-methyl-4-methoxydiphenylamine, N,N diphenyl-p-phenylenediamine, dianisidine, 3,3' dichlorobenzidine, 4,4'-diaminostilbene-2,2'-disulfonic 58 acid, benzylethylaniline, 1,8-naphthalenediamine, sodium naphthionate, Tobias acid, H acid, J acid, phenyl J acid, 1,4-diamino-anthraquinone, 1,4-diamino 2,3-dichloroanthraquinone, etc. 5 The aromatic isocyanate compound of the formula (p) includes 2,4-toluene diisocyanate, 2,6 toluene diisocyanate, m-phenylene diisocyanate, p phenylene diisocyanate, o-phenylene diisocyanate, etc. Of these, the toluene diisocynates are preferable, and 10 2,4-toluene diisocyanate is more preferable. The aromatic amine compound of the formula (q) is not particularly limited so long as it has one or more amino group directly bonded to one or more carbon atoms, respectively, of the benzene ring. In 15 addition, hydrogen atom(s) of the benzene ring may be replaced by an aromatic compound residue, an aliphatic compound residue, a heterocyclic compound residue, a hydroxyl group, a nitro group, a nitrile group, a carbamoyl group, a sulfamoyl group, a carboxyl group, a 20 nitroso group, an oxyamino group, a nitroamino group, a hydrazino group, a ureido group, an isocyanate group, a mercapto group, a sulfo group or a halogen atom. The aromatic amine compound of the formula (q) includes, for example, aromatic monoamines such as aniline, o 25 toluidine, m-toluidine, p-toluidine, o-anisidine, p anisidine, p-phenetidine, 2,4-dimethoxyaniline, 2,5 dimethoxyaniline, 3,4-dimethoxyaniline, p-amino acetanilide, carboxy-substituted anilines (e.g. p- 59 aminobenzoic acid), hydroxyl-substituted anilines (e.g. o-aminophenol, m-aminophenol, p-aminophenol and 2 amino-4-chlorophenol), 2,3-xylidine, 2,4-xylidine, 3,4 xylidine, 2,6-xylidine, nitrile-substituted anilines 5 (e.g. 4-aminobenzonitrile), anthranilic acid, p cresidine, halogen-substituted anilines (e.g. 2,5 dichloroaniline, 2,6-dichloroaniline, 3,4-dichloro aniline, 3,5-dichloroaniline, 2,4,5-trichloroaniline, o-chloroaniline, m-chloroaniline and p-chloroaniline), 10 a-naphthylamine, aminoanthracene, o-ethylaniline, methyl p-aminobenzoate, ethyl p-aminobenzoate, n-propyl p-aminobenzoate, isopropyl p-aminobenzoate, butyl p aminobenzoate, dodecyl p-aminobenzoate, benzyl p aminobenzoate, o-aminobenzophenone, m-aminoaceto 15 phenone, p-aminoacetophenone, m-aminobenzamide, o aminobenzamide, p-aminobenzamide, p-amino-N-methyl benzamide, 3-amino-4-methylbenzamide, 3-amino-4 methoxybenzamide, 3-amino-4-chlorobenzamide, carbamoyl anilines (e.g. p-(N-phenylcarbamoyl)aniline, p-[N-(4 20 chlorophenyl)carbamoyl]aniline, p-[N-(4-aminophenyl) carbamoyl]aniline, 2-methoxy-5-(N-phenylcarbamoyl) aniline, 2-methoxy-5-[N-(2'-methyl-3'-chlorophenyl) carbamoyl]aniline and 2-methoxy-5-[N-(2'-chlorophenyl) carbamoyl]aniline), 5-acetylamino-2-methoxyaniline, 4 25 acetylaminoaniline, 2-methoxy-4-(N-benzoylamino)-5 methylaniline, sulfamoylanilines (e.g. 4-sulfamoyl aniline, 3-sulfamoylaniline, 2-chloro-5-N-phenyl sulfamoylaniline, 2-methoxy-5-N,N-diethylsulfamoyl- 60 aniline and 2,5-dimethoxy-4-N-phenysulfamoylaniline), 2-(N-ethyl-N-phenylaminosulfonyl)aniline, 4-dimethyl aminosulfonylaniline, 4-diethylaminosulfonylaniline, sulfathiazole, 4-aminodiphenyl sulfone, 2-methoxy-5 5 benzylsulfonylaniline, 2-phenoxysulfonylaniline, 2-(2' chlorophenoxy)sulfonylaniline, 3-anilinosulfonyl-4 methylaniline, nitro-substituted anilines (e.g. o chloro-p-nitroaniline, o-nitro-p-chloroaniline, 2,6 dichloro-4-nitroaniline, 5-chloro-2-nitroaniline, o 10 nitroaniline, m-nitroaniline, p-nitroaniline, 2-methyl 4-nitroaniline, m-nitro-p-toluidine and 2-amino-5 nitrobenzonitrile), sulfanilic acid, metanilic acid, 4B acid, C acid, 2B acid, p-fluoroaniline, o-fluoro aniline, 3-chloro-4-fluoroaniline, 2,4-difluoroaniline, 15 2,3,4-trifluoroaniline, m-aminobenzotrifluoride, 2 amino-3-bromo-5-nitrobenzonitrile, etc.; aromatic monoamines having one or more substituents including carboxyl group, nitroso group, oxyamino group, nitroamino group, hydrazino group, ureido group, 20 isocyanate group, mercapto group, sulfo group, etc.; and aromatic diamines such as 4,4'-diamino-3,3' diethyldiphenylmethane, 4,4'-diaminobenzanilide, 3,5 diaminochlorobenzene, diaminodiphenyl ether, 3,3' dichloro-4,4'-diaminodiphenylmethane, 3,3'-dimethyl 25 4,4'-diaminodiphenylmethane, tolidine base, dianisidine, bis[4-(m-aminophenoxy)phenyl] sulfone, bis[4-(p-aminophenoxy)phenyl] sulfone, bis[3-methyl-4 (p-aminophenoxy)phenyl] sulfone, 3,3'-dimethoxy-4,4'- 61 diaminobiphenyl, 3,3'-dimethyl-4,4'-diaminobiphenyl, 2,2'-dichloro-4,4'-diamino-5,5'-dimethoxybiphenyl, 2,2',5,5'-tetrachloro-4,4'-diaminobiphenyl, o-tolidine sulfone, 2,4'-diaminobiphenyl, 2,2'-diaminobiphenyl, 5 4,4'-diaminobiphenyl, 2,2'-dichloro-4,4'-diamino biphenyl, 3,3'-dichloro-4,4'-diaminobiphenyl, 2,2' dimethyl-4,4'-diaminobiphenyl, 4,4'-thiodianiline, 2,2'-dithiodianiline, 4,4'-dithiodianiline, 4,4' diaminodiphenyl ether, 3,3'-diaminodiphenyl ether, 10 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl methane, 3,4'-diaminodiphenylmethane, bis(3-amino-4 chlorophenyl) sulfone, bis(3,4-diaminophenyl) sulfone, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfone, 3,3'-diamino 15 diphenylmethane, 4,4'-diaminodiphenylamine, 4,4' ethylenedianiline, 4,4'-diamino-2,2'-dimethyldibenzyl, 3,3'-diaminobenzophenone, 4,4'-diaminobenzophenone, 1,4-bis(4-aminophenoxy)benzene, 1,3-bis(4-amino phenoxy)benzene, 1,3-bis(3-aminophenoxy)benzene, 9,9 20 bis(4-aminophenyl)fluorene, 2,2-bis(4-aminophenoxy phenyl)propane, 4,4'-bis(4-aminophenoxy)diphenyl, dianisidine, 3,3'-dichlorobenzidine, etc. Of these, the aromatic monoamines are preferably used, and aniline or the aniline derivatives are more preferably 25 used. The isocyanate compound of the formula (r) is not particularly limited so long as it has two or more isocyanate groups bonded to carbon atoms, respectively.
62 This compound includes, for example, p-phenylene diisocyanate, m-phenylene diisocyanate, o-phenylene diisocyanate, 2,5-dimethoxybenzene-1,4-diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 5 diphenylmethane diisocyanate, o-tolidine diisocyanate, diphenyl ether diisocyanate, 1,5-naphthylene diisocyanate, dianisidine diisocyanate, 9-ethyl carbazole-3,6-diisocyanate, 3,3'-dimethyl-4,4' diphenylmethane diisocyanate, hexamethylene 10 diisocyanate, isophorone diisocyanate, triphenylmethane triisocyanate, tris(4-phenylisocyanate) thiophosphate, 4,4',4"-triisocyanato-2,5-dimethoxytriphenylamine, 4,4',4"-triisocyanatotriphenylamine, m-xylylene diisocyanate, lysine diisocyanate, dimer acid 15 diisocyanate, isopropylidene bis-4-cyclohexyl isocyanate, dicyclohexylmethane diisocyanate and methylcyclohexane diisocyanate. As the isocyanate compound of the formula (r), there may also be used diisocyanate dimers such as 20 N,N'-(4,4'-dimethyl-3,3'-diphenyldiisocyanato) urethodione (Desmodule TT, a trade name), a toluene diisocyanate dimer; and diisocyanate trimers such as 4,4',4"-trimethyl-3,3',3"-triisocyanato-2,4,6 triphenylcyanurate. There may also be used water 25 adduct isocyanates of toluene diisocyanate, diphenyl methane diisocyanate and the like, such as 1,3-bis(3 isocyanato-4-methylphenyl)urea; polyol adducts such as trimethylolpropane adducts of toluene diisocyanate 63 (Desmodule L and Coronate L, trade names); and amine adducts. There may also be used compounds having two or more isocyanate groups, among the isocyanate compounds and isocyanate adduct compounds described in 5 the specification of JP-A-10-76757 and the specifica tion of JP-A-10-95171 (the contents of these references are hereby incorporated herein by reference). Of the above-exemplified isocyanate compounds, aromatic isocyanates having isocyanate 10 groups bonded to a benzene ring are preferable. More preferable are p-phenylene diisocyanate, m-phenylene diisocyanate, o-phenylene diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, diphenylmethane diisocyanate, o-tolidine diisocyanate, diphenyl ether 15 diisocyanate, 1,5-naphthylene diisocyanate, triphenyl methane triisocyanate, N,N'-(4,4'-dimethyl-3,3' diphenyldiisocyanato)urethodione (Desmodule TT, a trade name), 4,4',4"-trimethyl-3,3',3"-triisocyanato-2,4,6 triphenylcyanurate, 1,3-bis(3-isocyanato-4-methyl 20 phenyl)urea, and trimethylolpropane adducts of toluene diisocyanate (Desmodule L and Coronate L, trade names). Especially preferable examples of the isocyanate compound of the formula (r) are toluene diisocyanates. Of the toluene diisocyanates, 2.4-toluene diisocyanate 25 is preferable. Besides 2.4-toluene diisocyanate, mixtures of 2.4-toluene diisocyanate and 2,6-toluene diisocyanate are generally on the market and available at a low price and may also be used as the isocyanate 64 compound of the formula (r). The amine compound of the general formula (s) is not particularly limited so long as it has two or more amino groups. This compound includes, for 5 example, aromatic amines such as 4,4'-diamino-3,3' diethyldiphenylmethane, 4,4'-diaminobenzanilide, 3,5 diaminochlorobenzene, diaminodiphenyl ether, 3,3' dichloro-4,4'-diaminodiphenylmethane, 3,3'-dimethyl 4,4'-diaminodiphenylmethane, tolidine base, 10 dianisidine, bis[4-(m-aminophenoxy)phenyl] sulfone, bis[4-(p-aminophenoxy)phenyll sulfone, bis[3-methyl-4 (p-aminophenoxy)phenyl] sulfone, 3,3'-dimethoxy-4,4' diaminobiphenyl, 3,3'-dimethyl-4,4'-diaminobiphenyl, 2,2'-dichloro-4,4'-diamino-5,5'-dimethoxybiphenyl, 15 2,2',5,5'-tetrachloro-4,4'-diaminobiphenyl, o-tolidine sulfone, 2,4'-diaminobiphenyl, 2,2'-diaminobiphenyl, 4,4'-diaminobiphenyl, 2,2'-dichloro-4,4'-diamino biphenyl, 3,3'-dichloro-4,4'-diaminobiphenyl, 2,2' dimethyl-4,4'-diaminobiphenyl, 4,4'-thiodianiline, 20 2,2'-dithiodianiline, 4,4'-dithiodianiline, 4,4' diaminodiphenyl ether, 3,3'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl methane, 3,4'-diaminodiphenylmethane, bis(3-amino-4 chlorophenyl) sulfone, bis(3,4-diaminophenyl) sulfone, 25 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfone, 3,3'-diamino diphenylmethane, 4,4'-diaminodiphenylamine, 4,4' ethylenedianiline, 4,4'-diamino-2,2'-dimethyldibenzyl, 65 3,3' -diaminobenzophenone, 4,4' -diaminobenzophenone, 1,4-bis(4-aminophenoxy)benzene, 1,3-bis(4-amino phenoxy)benzene, 1,3-bis(3-aminophenoxy)benzene, 9,9 bis(4-aminophenyl)fluorene, 2,2-bis(4-aminophenoxy 5 phenyl)propane, 4,4'-bis(4-aminophenoxy)diphenyl, dianisidine, 3,3'-dichlorobenzidine, tolidine base, o phenylenediamine, m-phenylenediamine, p-phenylene diamine, etc.; heterocyclic compound amines such as guanamine, acetoguanamine, 2,4-diamino-6-[2' 10 methylimidazolyl-(1)]ethyl-S-triazine, 2,3-diamino pyridine, 2, 5-diaminopyridine, 2,3, 5-triaminopyridine, bis(aminopropyl)piperazine, etc.; and aliphatic amines such as methanediamine, 1,2-diaminopropane, 1,3 diaminopropane, 1,4-diaminobutane, 1,3-diamino-2 15 hydroxypropane, ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, N-methyl 3,3'-iminobis(propylamine), hexamethylenediamine, bis(aminomethyl)cyclohexane, isophoronediamine, isopropylidenebis(aminocyclohexane), 4,4'-diamino 20 dicyclohexylmethane, xylylenediamine, etc. Of the above-exemplified amine compounds, the aromatic amines are preferable, and aniline derivatives having at least two amino groups and represented by the following formula (VIII) are especially preferable:
R
1
X
1 X2 R3 Y1 (VIII) R2 R4 66 wherein R 1 , R 2 , R 3 and R 4 are independently a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or an amino group, X, and X 2 are independently an amino group or a group represented by the formula (b): -O
NH
2 5 and Yi is any of -S0 2 -, -0-, -(S),-, -(CH 2 )n-, -CO-, -CONH-, -NH-, -CH (COOR 1 ) -, -C (CF 3 ) 2- -CR 2
R
3 - and a group represented by any of the formulas (a): 67
CH
3
CH
3
CH
3 CH 3 -C -- (a) I Ij
CH
3 CH 3 00 -- O
O--
0 or is absent, each of R 1 , R 2 and R 3 is an alkyl group, and n is 1 or 2. The amine compound of the general formula (t) includes aromatic amines such as aniline, o-toluidine, 5 m-toluidine, p-toluidine, o-anisidine, p-anisidine, p phenetidine, N, N-dimethyl-p-phenylenediamine, N, N diethyl-p-phenylenediamine, 2, 4-dimethoxyaniline, 2,5- 68 dimethoxyaniline, 3,4-dimethoxyaniline, p-amino acetanilide, p-aminobenzoic acid, o-aminophenol, m aminophenol, p-aminophenol, 2,3-xylidine, 2,4-xylidine, 3,4-xylidine, 2,6-xylidine, 4-aminobenzonitrile, 5 anthranilic acid, p-cresidine, 2,5-dichloroaniline, 2,6-dichloroaniline, 3,4-dichloroaniline, 3,5 dichloroaniline, 2,4,5-trichloroaniline, a-naphthyl amine, aminoanthracene, o-ethylaniline, o-chloro aniline, m-chloroaniline, p-chloroaniline, N 10 methylaniline, N-ethylaniline, N-propylaniline, N butylaniline, N,N-diglycidylaniline, N,N-diglycidyl-o toluidine, acetoacetic acid anilide, trimethylphenyl ammonium bromide, 4,4'-diamino-3,3'-diethyldiphenyl methane, 4,4'-diaminobenzanilide, 3,5-diaminochloro 15 benzene, diaminodiphenyl ether, 3,3'-dichloro-4,4' diaminodiphenylmethane, 3,3'-dimethyl-4,4'-diamino diphenylmethane, tolidine base, o-phenylenediamine, m phenylenediamine, p-phenylenediamine, 2-chloro-p phenylenediamine, dianisidine, methyl p-aminobenzoate, 20 ethyl p-aminobenzoate, n-propyl p-aminobenzoate, isopropyl p-aminobenzoate, butyl p-aminobenzoate, dodecyl p-aminobenzoate, benzyl p-aminobenzoate, o aminobenzophenone, m-aminoacetophenone, p-aminoaceto phenone, m-aminobenzamide, o-aminobenzamide, p 25 aminobenzamide, p-amino-N-methylbenzamide, 3-amino-4 methylbenzamide, 3-amino-4-methoxybenzamide, 3-amino-4 chlorobenzamide, p-(N-phenylcarbamoyl)aniline, p-[N-(4 chlorophenyl)carbamoyl]aniline, p-[N-(4-aminophenyl)- 69 carbamoyl]aniline, 2-methoxy-5-(N-phenylcarbamoyl) aniline, 2-methoxy-5-[N-(2'-methyl-3'-chlorophenyl) carbamoyl]aniline, 2-methoxy-5-[N-(2'-chlorophenyl) carbamoyl]aniline, 5-acetylamino-2-methoxyaniline, 4 5 acetylaminoaniline, 4-(N-methyl-N-acetylamino)aniline, 2,5-diethoxy-4-(N-benzoylamino)aniline, 2,5-dimethoxy 4-(N-benzoylamino)aniline, 2-methoxy-4-(N-benzoyl amino)-5-methylaniline, 4-sulfamoylaniline, 3 sulfamoylaniline, 2-(N-ethyl-N-phenylaminosulfonyl) 10 aniline, 4-dimethylaminosulfonylaniline, 4-diethyl aminosulfonylaniline, sulfathiazole, 4-aminodiphenyl sulfone, 2-chloro-5-N-phenylsulfamoylaniline, 2 methoxy-5-N,N-diethylsulfamoylaniline, 2,5-dimethoxy-4 N-phenysulfamoylaniline, 2-methoxy-5-benzylsulfonyl 15 aniline, 2-phenoxysulfonylaniline, 2-(2'-chloro phenoxy)sulfonylaniline, 3-anilinosulfonyl-4 methylaniline, bis[4-(m-aminophenoxy)phenyl] sulfone, bis[4-(p-aminophenoxy)phenyl] sulfone, bis[3-methyl-4 (p-aminophenoxy)phenyl] sulfone, 3,3'-dimethoxy-4,4' 20 diaminobiphenyl, 3,3'-dimethyl-4,4'-diaminobiphenyl, 2,2'-dichloro-4,4'-diamino-5,5'-dimethoxybiphenyl, 2,2',5,5'-tetrachloro-4,4'-diaminobiphenyl, o-tolidine sulfone, 2,4'-diaminobiphenyl, 2,2'-diaminobiphenyl, 4,4'-diaminobiphenyl, 2,2'-dichloro-4,4'-diamino 25 biphenyl, 3
,
3 '-dichloro-4,4'-diaminobiphenyl, 2,2' dimethyl-4,4'-diaminobiphenyl, 4,4'-thiodianiline, 2,2'-dithiodianiline, 4,4'-dithiodianiline, 4,4' diaminodiphenyl ether, 3,3'-diaminodiphenyl ether, 70 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl methane, 3,4'-diaminodiphenylmethane, bis(3-amino-4 chlorophenyl) sulfone, bis(3,4-diaminophenyl) sulfone, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl 5 sulfone, 3,4'-diaminodiphenyl sulfone, 3,3'-diamino diphenylmethane, 4,4-diaminodiphenylamine, 4,4' ethylenedianiline, 4,4'-diamino-2,2'-dimethyldibenzyl, 3,3'-diaminobenzophenone, 4,4'-diaminobenzophenone, 1,4-bis(4-aminophenoxy)benzene, 1,3-bis(4-amino 10 phenoxy)benzene, 1,3-bis(3-aminophenoxy)benzene, 9,9 bis(4-aminophenyl)fluorene, 2,2-bis(4-aminophenoxy phenyl)propane, 4,4'-bis(4-aminophenoxy)diphenyl, 3,3',4,4'-tetraaminodiphenyl ether, 3,3',4,4' tetraaminodiphenyl sulfone, 3,3',4,4'-tetraamino 15 benzophenone, 3-aminobenzonitrile, 4-phenoxyaniline, 3 phenoxyaniline, 4,4'-methylenebis-o-toluidine, 4,4'-(p phenyleneisopropylidene)-bis-(2,6-xylidine), o-chloro p-nitroaniline, o-nitro-p-chloroaniline, 2,6-dichloro 4-nitroaniline, 5-chloro-2-nitroaniline, 2-amino-4 20 chlorophenol, o-nitroaniline, m-nitroaniline, p nitroaniline, 2-methyl-4-nitroaniline, m-nitro-p toluidine, 2-amino-5-nitrobenzonitrile, Metol, 2,4 diaminophenol, N-(-hydroxyethyl)-o-aminophenol sulfate, sulfanilic acid, metanilic acid, 4B acid, C 25 acid, 2B acid, p-fluoroaniline, o-fluoroaniline, 3 chloro-4-fluoroaniline, 2,4-difluoroaniline, 2,3,4 trifluoroaniline, m-aminobenzotrifluoride, m toluylenediamine, 2-aminothiophenol, 2-amino-3-bromo-5- 71 nitrobenzonitrile, diphenylamine, p-aminodiphenylamine, octylated diphenylamine, 2-methyl-4-methoxydiphenyl amine, N,N-diphenyl-p-phenylenediamine, dianisidine, 3,3'-dichlorobenzidine, 4,4'-diaminostilbene-2,2' 5 disulfonic acid, benzylethylaniline, 1,8-naphthalene diamine, sodium naphthionate, Tobias acid, H acid, J acid, phenyl J acid, 1,4-diamino-anthraquinone, 1,4 diamino-2,3-dichloroanthraquinone, etc.; and heterocyclic compound amines such as 3-amino-1,2,4 10 triazole, 2-aminopyridine, 3-aminopyridine, 4 aminopyridine, a-amino-e-caprolactam, acetoguanamine, 2
,
4 -diamino-6-[2'-methylimidazolyl-(1)]ethyl-S triazine, 2,3-diaminopyridine, 2,5-diaminopyridine, 2,3,5-triaminopyridine, 1-amino-4-methylpiperazine, 1 15 (2-aminoethyl)piperazine, bis(aminopropyl)piperazine, N-(3-aminopropyl)morpholine, etc. Of these, the aromatic monoamines are preferably used. The alcohol compound of the general formula (u) is not particularly limited so long as it is a 20 polyol compound having two or more OH groups. The alcohol compound includes diols such as ethylene glycol, diethylene glycol, triethylene glycol, 1,3 propanediol, 1,2-propanediol, propylene glycol, dipropylene glycol, tripropylene glycol, 1,4 25 butanediol, 1,5-pentanediol, 1,6-hexanediol, hexylene glycol, 1,9-nonanediol, neopentyl glycol, methyl pentanediol, etc.; aliphatic polyols such as glycerin, castor oil, trimethylolpropane, trimethylolethane, 72 hexanetriol, pentaerythritol, a-methyl glucoside, sorbitol, sucrose, etc.; polyols such as polyethylene glycols, polypropylene glycols, polytetramethylene glycols, adipate-derived polyols, epoxy-modified 5 polyols, polyether ester polyols, polycarbonate polyols, polycaprolactone diols, amine-modified polyols, polyether polyols obtained by adding one of or a mixture of two or more of alkylene oxides (e.g. ethylene oxide and propylene oxide) to one of or a 10 mixture of two or more of polyhydric alcohols (e.g. glycerin and propylene glycol), acryl polyols, fluorinated polyols, polybutadiene polyols, polyhydroxy polyols, castor-oil-derived polyols, polymer polyols, halogen-containing polyols, phosphorus-containing 15 polyols, etc.; and alkanolamines such as N-alkyl diethanolamines, N-alkyldiisopropanolamines, triethanolamine, triisopropanolamine,
N,N,N',N'
tetrakis( 2 -hydroxyethyl)ethylenediamine,
N,N,N',N'
tetrakis(2-hydroxypropyl)ethylenediamine, etc. Of 20 these, the diols, the aliphatic polyols, the alkanol amines, and polyols having a molecular weight of 2,000 or less are preferably used. The amine compound of the general formula (XVII) includes, for example, aromatic diamines such as 25 4, 4 '-diamino-3,3'-diethyldiphenylmethane, 4,4'-diamino benzanilide, 3,5-diaminochlorobenzene, diaminodiphenyl ether, 3,3'-dichloro-4,4'-diaminodiphenylmethane, 3,3' dimethyl-4,4'-diaminodiphenylmethane, tolidine base, 73 dianisidine, bis[4-(m-aminophenoxy)phenyl] sulfone, bis[4-(p-aminophenoxy)phenyl] sulfone, bis[3-methyl-4 (p-aminophenoxy)phenyl] sulfone, 3,3'-dimethoxy-4,4' diaminobiphenyl, 3,3'-dimethyl-4,4'-diaminobiphenyl, 5 2,2'-dichloro-4, 4 '-diamino-5,5'-dimethoxybiphenyl, 2,2',5,5'-tetrachloro-4,4'-diaminobiphenyl, o-tolidine sulfone, 2,4'-diaminobiphenyl, 2,2'-diaminobiphenyl, 4,4'-diaminobiphenyl, 2,2'-dichloro-4,4'-diamino biphenyl, 3
,
3 '-dichloro-4,4'-diaminobiphenyl, 2,2' 10 dimethyl-4,4'-diaminobiphenyl, 4,4'-thiodianiline, 2,2'-dithiodianiline, 4,4'-dithiodianiline, 4,4' diaminodiphenyl ether, 3,3'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl methane, 3,4'-diaminodiphenylmethane, bis(3-amino-4 15 chlorophenyl) sulfone, bis(3,4-diaminophenyl) sulfone, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfone, 3,3'-diamino diphenylmethane, 4,4'-diaminodiphenylamine, 4,4' ethylenedianiline, 4,4'-diamino-2,2'-dimethyldibenzyl, 20 3,3'-diaminobenzophenone, 4,4'-diaminobenzophenone, 1,4-bis(4-aminophenoxy)benzene, 1,3-bis(4-amino phenoxy)benzene, 1,3-bis(3-aminophenoxy)benzene, 9,9 bis(4-aminophenyl)fluorene, 2,2-bis(4-aminophenoxy phenyl)propane, 4,4'-bis(4-aminophenoxy)diphenyl, 25 dianisidine, 3,3'-dichlorobenzidine, etc. Amine compounds of the general formula (XVII) in which y 1 is a sulfonyl group or a methylene group are preferable. For obtaining each of the urea-urethane 74 compounds of the first to fourth aspects of the present invention, the isocyanate and the corresponding reactants are mixed to be reacted in an organic solvent or without a solvent, after which filtration, crystal 5 lization, desolvation, etc. are carried out to collect crystals, whereby the desired compound is obtained. The reaction may be carried out by a method in which a material having two or more groups in the molecule is used in large excess and another material to be reacted 10 with the groups is added thereto in small portions. When this method is adopted, it is possible to react only one of the two or more groups. In the addition, it is preferable to stir the system thoroughly to effect sufficient dispersion of the added material 15 immediately after the addition. The above applies to any of the urea-urethane compounds exemplified herein. A method for the reaction is not limited to the above method and any method may be adopted so long as the same result as above can be obtained. As each of the 20 reactants, one or more compounds may be used depending on purposes. As the solvent, any solvent may be used so long as it does not react with an isocyanate group and the functional groups of the reactants. The solvent includes, for example, aliphatic hydrocarbons, 25 alicyclic hydrocarbons, aromatic hydrocarbons, chlorinated aliphatic hydrocarbons, chlorinated aromatic hydrocarbons, chlorinated alicyclic hydro carbons, and ketones. Methyl ethyl ketone, toluene and 75 the like are especially preferable which dissolve the isocyanate and in which the reaction product has a low solubility. The reaction product obtained by the above reaction procedure is not always a single compound, but 5 is obtained as a mixture of compounds different in the position of a substituent, in some cases. Specific examples of the urea-urethane compounds of the first to fourth aspects of the present invention are the following compounds ((S-1) to (S 10 70)). (S-1) H N oC2Hs O N N N H H H (S-2) i 7 0 N
C
2
H
5 , IC- NA:) ~ -- CI N" H H H (S-3) n- 4H 0 N n-C3H7N , H .C H H H
H
3 C H H H
H
3 C (S-5) 0 0 nCH, 0 N" NN11" N"' H H H 76
H
3 C (S-6) 0o o-4H, 0IIC-N 'N, N"" H H H
H
3 C (S-7) 0 0
S-CAH
9 , 0 I.C"- ~ N-,l H H H (S-8) 0 0 3 0 o lc* N a N I-lNa H H H
H
3 C 0I 0 (S-9)11 11 n-613,0 llc*,N N INNc H H H
H
3 C (S-10) 111 n-CloH21N- -C'- N. Nolll " H H H
H
3 C (S-11) I n-C 1 8H37N,,0I-1" CN):,Nllc o H H H
H
3 C (S-12) 00 a c 1C1N)"N *N. N"'
H
2 H H H (S-13)
CH
3 0iH 3
H
3 C ,'l A 3! N l IH 0 NN 0N N N N 0N
H
77 (S-14) H 11 _
H
3 C
C
2
H
5 2K 'A AK "k~ii AK, ,C2H5 0 N :::N N'a N N N 0 H H H H H H (S-15) 0 -C37K l ONA Nk 0i 111N .k[ .kA-C3H7 00N I N Na N X)N 0 (S-16)
~CH
3 1II
H
3 C~ i-37ol NI 6 I o : ) < )LN IK l.A l -C 3
H
7 0- 3 7 ~N A N N N ::N 0 (S-17) 0 fl 4 S%0~jA 0 0 0KACH o-A N Na0 N N Nk 0 ACH (S-18) 0 o 0 1 i-CAH, AK ja 1NK .1- Ik NN I -CAH H H H N N 0 (S-19) 0
S-C
4
H
9 ,~ 'Al A'a K kACH o N N N N 0 (S-20) ~CH3 N0 I N C 3 K P W 78 (S-21)
K>CH
3 1 C-O N )IOJ&OQN '-0-d
H
2 HH2HH (S-22) n-C 4 HgO-C 2
H
4 -OJI I" N NO-C 2 HCO-n-C 4
H
9 H HH H1 (S-23)
O-C
2
H
4 -0 Oo N N O-C2HgO 0 FI HH H H H (S-24) 0 OCHO3 O O
H
3 CfO-C 3
H
7 . S('Z IN 0 NO ' NI0 O-(C 3 H-0tCH 3 HYH H H~ H2 (S-25) H3C-O N -CH 3 3HH H (S-26)
CH
3 HHC o<0 0 : 0 H3fo a I" I4 IN N-CH 3 H H H (S-27) CH H3C H3C--O N:NkN N O-CH3 P W 79 (S-28) N N- I~ HC H H (S-29) CH O C-C N O-C-C O N I H2 H 2 H H (S-30) C H2 H 3 C H (S 3)N @N ~ H2-- O3 H30 H - -O - - - N0C- NN N H H -- N N (S-31) 0 r~CH3 CH 011011 H HH 2 H H ( -32) 0 H H H H
H
2 C- 0 H 3 C0 N N 0 H 3 CO H H HI N NJQ H H 80 (S-33)
CH
3 00 -N N N HH
H
2 C-O 0
CH
3 O
C
2 H---- --- N H r-a NN
H
2 C-O
CH
3 H H CNN NN H H (S-34)
H
3 C 0 0 N-- C-C-0-C-N N N (S-35) H3C I 0 C-N -O-C-NN ] 4 CH3 (S-36) 0 C H3Co N N N H H H (S-37) C N N N C25,0 I-CIN N ICN " H H H (S-38) n-C 3 H0N N N 0 N N N HH H 81 (339 9 ~CH 3 (S-39) N N N H H H
CH
3 (S-40) O N 9 n-C 4
H
9 e N CIN N H H H CH3 (S-4) N N N (S -44) n-CeH13 O N N N-c~lW H H H (S-42) n-C H 21 O N N (S -46) n-C H3 O l N N N H H H (S-4) N N N H H H o-61,,N N N N'O H H H (S-45) 0
CH
3 0 nC oH2- -c* N N N"' H H H (S-46) 0 j H 0 n-CISH 37 I 3-,0 I-cN NIc~ N'C H H H ( S - 4 7 ) 0C H 3 0 -C- ICIO" N N ANI"* N'
H
2 H H H 82 (S-48) HA 3 C11 CH3
H
3 C,-J A" Ilk~
~C
3 I I I N 0 H H HH HH (S-49)
H
3 C H
C
2
H
5 ... .,rN- 2
H
5 N N I N 0 H H HH (S-50) 00 0 -2C3Hi~'J %~ CH 7-,H A-CN3H7~ H H, H H (S-51) H3
~CH
3 '-37 N 2 A, 1: 'L Ii-C 3
H
7 0I~a I 'a N NJ H HH H (S-52) f-C 4
H
9 %2K0c l2K ,-C4H 9 ' CI I Ia N "k0 (S-53)
H
3 C ~ 0CH 3 i-CAH, K -. K '- 0 1 .~ - A -li-C 4
H
9 o' N:) N N'O I N N N0 (S-54) H3CX 0CH 3 S-C4H9.. 2K ~ .A 2 -C4H9 oN aN N N N N 0 H HH H H (S-55) 0 ~NN 83 (S-56) 03 00H N~ N N~N OCA
H
2 H H HI H (S-57)
H
3 C 0CH 3 n-C 4 Hg-O -C 2 H-O' N)chIN N N 0 , OCH40nC HH H HH (S-58)
H
3 C0 H 0L 0CH ~ A ~ K H H H H (S-5 9) HA 0 CH 3 (S-60)
H
3 C
H
2 ~ CH 3 0 0 I 0
H
3 C-N N N o N N 0-CH 3 H H H H H (S-61) H3 K>CH3
CH
3 H0 0C~i j 0 3C-Olk INN 0k -CH3 HH (S-62)
H
3 C CH 3
H
3 C-0o NN NNO-C-H 3 H H H (S-63) N N N OCC0 N~ N N H H H H H H 84 (S-64) N N C-C-O NN N I HI HI (S-65) pl H3CCH 3 0CH 3 0 [i0 0 H 2 1 N N rjNf):> O-C-CH-O I- Nj A ," HI HH H (S-66) H C C-H-H H C-N-r-O N H~ H' HS-6-) 0 OH 3 HC-O-C- N , N,1N H 2 -0 C H H 2C0 3 oH C-N NN O H~ H J: (S-60
H
3 C 3 0 -N H N I' HI H
H
2 C-/u 0 H 3 C Hl ' I H 2 I CH-C-C-0-C- ~ IH N N* 02 - H C H H H N N H H M W 85 (-69) Ja
H
3 0 11
H
2
H
2 N H3 N-C-C-0-C-N N N HH H _j3 (S-70)
HCH
3 0 H2 11 IC C--C-O-C-N N N HH H 4 Each of the urea-urethane compositions according to the fifth to twelfth aspects of the present invention and the urea-urethane compositions produced by the production processes of the thirteenth 5 to twentieth aspects of the invention preferably comprises 50 wt% or more, more preferably 60 wt% or more, further preferably 70 wt% or more of a urea urethane compound having in the molecule at least one urethane group (-NHCOO- group) and at least one urea 10 group (-NHCONH- group) in a total number of 2 to 10 and having a molecular weight of 5,000 or less. Such a urea-urethane composition can be used in combination with a colorless or light-colored dye precursor in order to obtain a color-producing composi 15 tion for a heat-sensitive recording material or a pressure-sensitive recording material. This color producing composition is so effective that it is excellent in both color-producing capability and print preservability.
86 The urea-urethane compound as the main constituent of the urea-urethane composition has at least one urea group and at least one urethane group in the molecule. The urea group and the urethane group 5 are preferably adjacent to each other through at least one compound residue (such a structure portion is hereinafter referred to as a urea-urethane structure portion). The total number of the urethane group(s) and the urea group(s) is not more than 10 and not less 10 than 2, preferably not more than 10 and not less than 3, more preferably not more than 10 and not less than 4. The ratio of urethane group(s) to urea group(s) in a molecule of the urea-urethane compound is 15 preferably 1 : 3 to 3 : 1, more preferably 1 : 2 to 2 1, most preferably 1 : 1. The molecular weight of the urea-urethane compound is 5,000 or less, preferably 2,000 or less. The content of the urea-urethane compound in 20 each of the urea-urethane compositions according to the fifth to twentieth aspects of the present invention is 50 wt% or more. Such a urea-urethane composition can be produced by a relatively simple production process. On the other hand, it can exhibit excellent performance 25 characteristics because of the high proportion of the urea-urethane compound capable of exhibiting excellent color-developing capability and preserving capability which are required of a color-producing composition.
87 In addition, as the urea-urethane compound, either a single compound or a mixture of two or more compounds including isomers may be used. Furthermore, a mixture of two or more 5 compounds including isomers may be used as the urea urethane compound in order to improve the color developing capability, preserving capability and the like. On the other hand, the urea-urethane compound 10 of the present invention may be properly diluted with a material that does not lessen the effects of the present invention. Such a diluent includes, for example, the heat-meltable materials, acidic developers, amine compounds, isocyanate compounds, urea 15 compounds, urethane compounds and the like, which are described hereinafter. Of these, the urea compounds and the urethane compounds, which have a structure similar to that of the urea-urethane compound, are preferable because they can improve the sensitivity. 20 In addition, compounds obtained by reacting a polyisocyanate compound with a hydroxy compound or an amino compound are preferable. Such a diluent is preferably contained in the resulting dilution in a proportion of 0.0001 to 50 wt% based on the total 25 weight of the urea-urethane compound and the diluent. The content of the diluent is more preferably 40 wt% or less, still more preferably 30 wt% or less, for the exhibition of the preserving capability. The content 88 of the diluent is more preferably 0.01 wt% or more, still more preferably 1 wt% or more, for improving the sensitivity. Such a diluent is produced during the synthetic reaction of the urea-urethane compound in 5 some cases. When the diluent is added, its addition during the synthetic reaction is preferable for improv ing the sensitivity. For example, preferable is a urea-urethane composition comprising a diluent and a urea-urethane compound having at least one urea group 10 and at least one urethane group in a total number of 2 to 10 in the molecular structure and having a molecular weight of 5,000 or less, which is characterized by comprising the diluent in a proportion of 0.0001 to 50 wt%. The same effect is observed also in the case of 15 the compositions of the eighth to twelfth aspects of the present invention and the compositions produced by the production processes of the thirteenth to twentieth aspects of the invention. Each of the urea-urethane compositions 20 according to the fifth to twentieth aspects of the present invention is preferably a colorless or light colored solid having a melting point, from the view point of utility in a heat-sensitive recording material. The melting point of the composition is 25 preferably 40*C to 300*C, more preferably 60 0 C to 260 0 C. As a process for producing any of the urea urethane compositions according to the fifth to 89 twentieth aspects of the present invention, there is preferably adopted a process of forming one or more urethane groups from at least one of the isocyanate groups of a polyisocyanate compound and the hydroxyl 5 group(s) of a hydroxy compound, and then forming one or more urea groups from the remaining unreacted isocyanate group(s) of the same polyisocyanate compound and the amino group(s) of an amino compound; or a process of forming one or more urea groups from at 10 least one of the isocyanate groups of a polyisocyanate compound and the amino group(s) of an amino compound, and then forming one or more urethane groups from the remaining unreacted isocyanate group(s) of the same polyisocyanate compound and the hydroxyl group(s) of a 15 hydroxy compound. When one or more urethane groups are formed from a polyisocyanate compound and a hydroxy compound, the urea-urethane composition can be efficiently obtained by using the polyisocyanate compound in an 20 excess amount over hydroxyl group(s), bonding the polyisocyanate compound to the hydroxy compound in an amount of one molecule per hydroxyl group of the hydroxy compound to react only one of the isocyanate groups of the polyisocyanate compound and leave at 25 least one of the isocyanate groups unreacted, and then reacting the remaining unreacted isocyanate group(s) with an amino compound to form one or more urea groups. In this case, it is preferable to form one or more 90 urethane groups by reacting the polyisocyanate compound with the hydroxy compound so that the ratio of the number of moles of the polyisocyanate compound to the number of hydroxyl equivalents of the hydroxy compound 5 becomes 100/1 to 1/2, and that the ratio of the number of isocyanate group equivalents of the polyisocyanate compound to the number of hydroxyl equivalents of the hydroxy compound becomes 1000/1 to 1/1. In adding the hydroxy compound to the 10 polyisocyanate compound, the hydroxy compound is preferably added in small portions so that the polyisocyanate compound is always present in the reaction system in an excess amount over hydroxyl group(s). Such an adding method is preferable particu 15 larly when the reaction is carried out at a ratio of the number of moles of the polyisocyanate compound to the number of hydroxyl equivalents of the hydroxy compound of near 1/1, for example, 5/1 to 1/2. Similarly, when one or more urea groups are 20 formed from a polyisocyanate compound and an amino compound, the urea-urethane composition can be efficiently obtained by using the polyisocyanate compound in an excess amount over amino group(s), bonding the polyisocyanate compound to the amino 25 compound in an amount of one molecule per amino group of the amino compound to react one of the isocyanate groups of the polyisocyanate compound and leave at least one of the isocyanate groups unreacted, and then 91 reacting the remaining unreacted isocyanate group(s) with a hydroxy compound to form one or more urethane groups. In this case, it is preferable to form one or more urea groups by reacting the polyisocyanate 5 compound with the amino compound so that the ratio of the number of moles of the polyisocyanate compound to the number of amino equivalents of the amino compound becomes 100/1 to 1/2, and that the ratio of the number of isocyanate group equivalents of the polyisocyanate 10 compound to the number of amino equivalents of the amino compound becomes 1000/1 to 1/1. In adding the amino compound to the poly isocyanate compound, the amino compound is preferably added in small portions so that the polyisocyanate 15 compound is always present in the reaction system in an excess amount over amino group(s). Such an adding method is preferable particularly when the reaction is carried out at a ratio of the number of moles of the polyisocyanate compound to the number of amino 20 equivalents of the amino compound of near 1/1, for example, 5/1 to 1/2. In a process for producing any of the urethane-urea compositions according to the fifth to twentieth aspects of the present invention, the 25 reaction of a polyisocyanate compound with a hydroxy compound for forming one or more urethane groups is preferably carried out without a solvent or by adding, dropping or pouring the hydroxy compound without a 92 solvent, a dilution of the hydroxy compound with a solvent or a dispersion of the hydroxy compound in a solvent continuously or by portions to a dilution of the polyisocyanate compound with a solvent or a 5 dispersion of the polyisocyanate compound in a solvent. Similarly, the reaction of a polyisocyanate compound with an amino compound for forming one or more urea groups may be carried out without a solvent or by adding, dropping or pouring the amino compound without 10 a solvent, a dilution of the amino compound with a solvent or a dispersion of the amino compound in a solvent continuously or by portions to a dilution of the polyisocyanate compound with a solvent or a disper sion of the polyisocyanate compound in a solvent. 15 The above production process comprising adding a hydroxy compound or an amino compound to a polyisocyanate compound in small portions is preferable particularly in the following case: in a reaction process for the production of the urea-urethane 20 composition, while leaving at least one of the isocyanate groups in molecules of the polyisocyanate compound, the other isocyanate group(s) is reacted with the hydroxy compound or the amino compound to form one or more urethane groups or urea groups, respectively. 25 Moreover, said production process is preferable when a hydroxy compound having two or more hydroxyl groups or an amino compound having two or more amino groups is reacted with a polyisocyanate compound having two or 93 more isocyanate groups. In carrying out the above reactions, it is preferable to stir the system thoroughly so that the hydroxy or amino compound added, dropped or poured into 5 the polyisocyanate is immediately and sufficiently dispersed. It is preferable to stir the reaction system thoroughly, for example, by adjusting the stir ring rate in a reactor, choosing an agitating blade or setting a baffle plate. 10 It is preferable to carry out the reaction for forming one or more urethane groups and the reaction for forming one or more urea groups, individu ally and successively. When they are carried out at the same time, the urea-urethane compound content of 15 the urea-urethane composition is undesirably decreased. It is preferable to carry out these urethane group forming reaction and urea group forming reaction continuously. In the process of the present invention, since separation and purification steps are not 20 necessary in the course of the production, the produc tion can be simplified by carrying out the two reaction steps continuously. In the production of any of the urea-urethane compositions according to the fifth to twentieth 25 aspects of the present invention, when a polyisocyanate adduct with a hydroxy compound is used which is an isocyanate already having one or more urethane groups in the molecule, the urea-urethane composition can be 94 obtained by reacting this adduct with an amino compound. In this case, it is preferable to form one or more urea groups by carrying out the reaction at an equivalent ratio of isocyanate group to amino group of 5 2/1 to 1/100, and remove the unreacted amino compound. In the production of any of the urea-urethane compositions according to the fifth to twentieth aspects of the present invention, when a polyisocyanate adduct with an amino compound is used which is an 10 isocyanate already having one or more urea groups in the molecule, the urea-urethane composition can be obtained by reacting this adduct with a hydroxy compound. In this case, it is preferable to form one or more urethane groups by carrying out the reaction at 15 an equivalent ratio of isocyanate group to hydroxyl group of 2/1 to 1/100, and remove the unreacted hydroxy compound. When a solvent is used for carrying out the reaction(s) in the production of any of the urea 20 urethane compositions according to the fifth to twentieth aspects of the present invention, the solvent is not particularly limited so long as it does not react with an isocyanate group and the like. The solvent includes, for example, aliphatic hydrocarbons, 25 alicyclic hydrocarbons, aromatic hydrocarbons, chlorinated aliphatic hydrocarbons, chlorinated aromatic hydrocarbons, chlorinated alicyclic hydro carbons, ketones and phosphoric esters. Acetone, 95 methyl ethyl ketone, toluene and the like are especially preferable which dissolve the isocyanate and in which the reaction product has a low solubility. When a high dissolving power for the isocyanate is 5 necessary, the phosphoric esters, in particular, trimethyl phosphate are preferable. When such a solvent is used, the formation of one or more urethane groups and the formation of one or more urea groups are preferably carried out in one and 10 the same solvent in order to make it easy to reuse the solvent and carry out the reaction for the urea group formation and the reaction for the urethane group formation continuously. The reaction temperature at which a poly 15 isocyanate is reacted with a hydroxy compound and/or an amino compound to form one or more urethane groups and/or one or more urea groups is OC to 3000C, prefer ably 5*C to 200 0 C, more preferably 100C to 1500C. The reaction temperature is properly adjusted depending on 20 the polyisocyanate compound, hydroxy compound and amino compound selected. It is also possible to carry out the urethane group formation and the urea group forma tion at different temperatures suitable for the formations, respectively. 25 A catalyst may be used for reacting a polyisocyanate with a hydroxy compound and/or an amino compound to form one or more urethane groups and/or one or more urea groups. The catalyst includes, for 96 example, tertiary amine compounds such as triethyl amine, 1,4-diazabicyclo(2,2,2)octane, etc.; and organic acid tin salts such as dibutyltin dilaurate, etc. Usually, the catalyst concentration is 1 to 10,000 ppm, 5 preferably 10 to 2,000 ppm, relative to the isocyanate compound. Of the above-exemplified catalysts, the tertiary amine compounds are preferable. A urea-urethane composition containing a urea-urethane compound having a plurality of urea 10 urethane structure portions in the molecule can be obtained by repeating the steps of the production process of the present invention two or more times by using, for example, an amino compound having two or more amino groups and a hydroxy compound having two or 15 more hydroxyl groups. Since a sufficiently high yield from reaction can be attained in each step, the production process of the present invention permits relatively easy production of a urea-urethane composi tion having high performance characteristics. 20 The polyisocyanate compound used in each of the fifth to twentieth aspects of the present invention is not particularly limited so long as it has two or more isocyanate groups bonded to carbon atoms, respec tively. The polyisocyanate compound includes, for 25 example, p-phenylene diisocyanate, m-phenylene diisocyanate, o-phenylene diisocyanate, 2,5-dimethoxy benzene-1,4-diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, diphenylmethane diisocyanate, 97 o-tolidine diisocyanate, diphenyl ether diisocyanate, 1,5-naphthylene diisocyanate, dianisidine diisocyanate, 9-ethylcarbazole-3,6-diisocyanate, 3,3'-dimethyl-4,4' diphenylmethane diisocyanate, hexamethylene 5 diisocyanate, isophorone diisocyanate, triphenylmethane triisocyanate, tris(4-phenylisocyanate) thiophosphate, 4,4',4"-triisocyanato-2,5-dimethoxytriphenylamine, 4,4',4"-triisocyanatotriphenylamine, m-xylylene diisocyanate, lysine diisocyanate, dimer acid 10 diisocyanate, isopropylidene bis-4-cyclohexyl isocyanate, dicyclohexylmethane diisocyanate and methylcyclohexane diisocyanate. As the polyisocyanate compound, there may also be used diisocyanate dimers such as N,N'-(4,4'-dimethyl-3,3'-diphenyldiisocyanato) 15 urethodione (Desmodule TT, a trade name), a toluene diisocyanate dimer; and diisocyanate trimers such as 4,4',4"-trimethyl-3,3',3"-triisocyanato-2,4,6 triphenylcyanurate. There may also be used water adduct isocyanates of toluene diisocyanate, diphenyl 20 methane diisocyanate and the like, such as 1,3-bis(3 isocyanato-4-methylphenyl)urea; polyol adducts such as trimethylolpropane adducts of toluene diisocyanate (Desmodule L and Coronate L, trade names); and amine adducts. There may also be used compounds having two 25 or more isocyanate groups, among the isocyanate compounds and isocyanate adduct compounds described in the specification of JP-A-10-76757 and the specifi cation of JP-A-10-95171 (the contents of these refer- 98 ences are hereby incorporated herein by reference). The above-exemplified compounds may be used singly or in combination. Of the above-exemplified compounds, prefer 5 able examples of the polyisocyanate compound are aromatic polyisocyanates having isocyanate groups bonded to a benzene ring, such as p-phenylene diisocyanate, m-phenylene diisocyanate, o-phenylene diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene 10 diisocyanate, diphenylmethane diisocyanate, o-tolidine diisocyanate, diphenyl ether diisocyanate, 1,5 naphthylene diisocyanate, triphenylmethane triisocyanate, N,N'-(4,4'-dimethyl-3,3'-diphenyl diisocyanato)urethodione (Desmodule TT, a trade name), 15 4,4',4"-trimethyl-3,3',3"-triisocyanato-2,4,6 triphenylcyanurate, 1,3-bis(3-isocyanato-4 methylphenyl)urea, trimethylolpropane adducts of toluene diisocyanate (Desmodule L and Coronate L, trade names), etc. Especially preferable examples of the 20 polyisocyanate compound are toluene diisocyanates. Of the toluene diisocyanates, 2.4-toluene diisocyanate is preferable. Besides 2.4-toluene diisocyanate, mixtures of 2.4-toluene diisocyanate and 2,6-toluene diiso cyanate are generally on the market and available at a 25 low price and may also be used as the polyisocyanate compound. As the hydroxy compound that is reacted with the polyisocyanate compound to form one or more 99 urethane groups, phenolic compounds and alcohol compounds are mentioned. The phenolic compounds include, for example, phenol, cresol, xylenol, p-ethylphenol, o-isopropyl 5 phenol, resorcinol, p-tert-butylphenol, p-tert octylphenol, 2-cyclohexylphenol, 2-allylphenol, 4 indanol, thymol, 2-naphthol, p-nitrophenol, o-chloro phenol, p-chlorophenol, 2,2-bis(4-hydroxyphenyl) propane, 2,2-bis(hydroxyphenyl)butane, 2,2-bis(hydroxy 10 phenyl)pentane, 2,2-bis(hydroxyphenyl)heptane, catechol, 3-methylcatechol, 3-methoxycatechol, pyrogallol, hydroquinone, methylhydroquinone, 4 phenylphenol, p,p'-biphenol, 4-cumylphenol, butyl bis(4-hydroxyphenyl)acetate, benzyl bis(4-hydroxy 15 phenyl)acetate, bis(4-hydroxyphenyl) sulfone, bis(3 methyl-4-hydroxyphenyl) sulfone, bis(3,5-dimethyl-4 hydroxyphenyl) sulfone, 4-hydroxyphenyl-4'-methylphenyl sulfone, 3-chloro-4-hydroxyphenyl-4'-methylphenyl sulfone, 3,4-dihydroxyphenyl-4'-methylphenyl sulfone, 20 4-isopropyloxyphenyl-4'-hydroxyphenyl sulfone, bis(2 allyl-4-hydroxyphenyl) sulfone, 4-hydroxyphenyl-4' benzyloxyphenyl sulfone, 4-isopropylphenyl-4' hydroxyphenyl sulfone, 4-hydroxy-4'-isopropoxydiphenyl sulfone, bis(2-methyl-3-tert-butyl-4-hydroxyphenyl) 25 sulfide, 4,4'-dihydroxydiphenyl ether, 4,4' thiodiphenol, 4,4'-dihydroxybenzophenone, 2,2-bis(4 hydroxyphenyl)hexafluoropropane, 4,4'-dihydroxy diphenylmethane, 3,3'-dihydroxydiphenylamine, bis(4- 100 hydroxy-3-methylphenyl) sulfide, bis(4-(2-hydroxy) phenyl) sulfone, 2,4-dihydroxybenzophenone, 2,2',4,4' tetrahydroxybenzophenone, phenyl salicylate, salicylanilide, methyl 4-hydroxybenzoate, benzyl 4 5 hydroxybenzoate, (4'-chlorobenzyl) 4-hydroxybenzoate, ethyl 1,2-bis(4'-hydroxybenzoate), pentyl 1,5-bis(4' hydroxybenzoate), hexyl 1,6-bis(4'-hydroxybenzoate), dimethyl 3-hydroxyphthalate, stearyl gallate, lauryl gallate, methyl gallate, 4-methoxyphenol, 4 10 (benzyloxy)phenol, 4-hydroxybenzaldehyde, 4-n octyloxysalicylic acid, 4-n-butyloxysalicylic acid, 4 n-pentyloxysalicylic acid, 3-n-dodecyloxysalicylic acid, 3-n-octanoyloxysalicylic acid, 4-n-octyloxy carbonylaminosalicylic acid and 4-n-octanoyloxy 15 carbonylaminosalicylic acid. Of the above-exemplified phenolic compounds, phenol, phenol derivatives represented by the following formula (w) and diphenol compounds represented by the following formula (XVI) are preferable. / \ OH (w) 20 wherein hydrogen atom(s) of the benzene ring may be replaced by an alkyl group, a cycloalkyl group, a phenyl group, an amide group, an alkoxyl group, a nitro group, a nitrile group, a halogen atom, a formyl group, a dialkylamino group, a toluenesulfonyl group, a 25 methanesulfonyl group or an OH group; and 101 HO 8 OH (XVI) wherein hydrogen atom(s) of each benzene ring may be replaced by a substituent which is preferably an aromatic compound residue, an aliphatic compound residue or a heterocyclic compound residue though the 5 substituent may be a hydroxyl group, a nitro group, a nitrile group, a carbamoyl group, a sulfamoyl group, a carboxyl group, a nitroso group, an amino group, an oxyamino group, a nitroamino group, a hydrazino group, a ureido group, an isocyanate group, a mercapto group, 10 a sulfo group or a halogen atom, each of the residues may have one or more substituents, 6 is a group selected from the group consisting of -S0 2 -, -0-, -(S)I-,
-(CH
2 ) -, -CO-, -CONH-, -NH-, -CH (COOR 1 ) -, -C (CF 3 ) 2 - and
-CR
2
R
3 - or is absent, R 1 , R 2 and R 3 are independently an 15 alkyl group, and n is 1 or 2. The term "aliphatic" used in the case of the fifth to twentieth aspects of the present invention includes the term "alicyclic". The term "aliphatic compound residue" used in 20 the case of the fifth to twentieth aspects of the present invention means a residue bonded by the carbon atom of the aliphatic hydrocarbon portion in the residue. The term "aromatic compound residue" used therein means a residue bonded by the carbon atom of 25 the aromatic ring such as benzene ring in the residue.
102 The term "heterocyclic compound residue" used therein means a residue bonded by the carbon atom forming the heterocyclic ring in the residue. Preferable examples of the substituent of the 5 aliphatic compound residue, heterocyclic compound residue or aromatic compound residue are alkyl groups, cycloalkyl groups, phenyl group, amide group, alkoxyl groups, nitro group, nitrile group, halogen atoms, formyl group, dialkylamino groups, toluenesulfonyl 10 group and methanesulfonyl group. As the alcohol compounds, compounds having at least one OH group bonded to the carbon atom of an aliphatic compound are mentioned. Examples of the alcohol compounds are the alcohols described in Solvent 15 Handbook, Kodansha Scientific Co., Ltd., the ninth impression (1989), pp. 327-420 and pp. 772-817. The alcohol compound includes, for example, aliphatic alcohols such as methanol, ethanol, propanol, isopropanol, n-butanol, isobutanol, sec-butanol, tert 20 butanol, pentanol, cyclopentanol, tert-amyl alcohol, 2 pentanol, isoamyl alcohol, hexanol, 3-hexanol, cyclo hexanol, cyclohexylmethanol, 4-methyl-2-pentanol, heptanol, isoheptanol, octanol, 2-ethyl-1-hexanol, capryl alcohol, nonyl alcohol, isononyl alcohol, 25 decanol, undecyl alcohol, dodecyl alcohol, tridecyl alcohol, tetradecyl alcohol, hexadecyl alcohol, octadecyl alcohol, isostearyl alcohol, etc.; unsaturated aliphatic alcohols such as ally alcohol, 2- 103 methyl-2-propen-1-ol, crotyl alcohol, propargyl alcohol, etc.; aliphatic alcohols having an aromatic compound residue bonded thereto, such as benzyl alcohol, cinnamyl alcohol, etc.; aliphatic alcohols 5 having a heterocyclic compound residue bonded thereto, such as 2-pyridinemethanol, 3-pyridinemethanol, 4 pyridinemethanol, furfuryl alcohol, etc.; halogenated aliphatic alcohols such as 2-chloroethanol, 1-chloro-3 hydroxypropane, etc.; glycol ethers such as ethylene 10 glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monoisobutyl ether, ethylene glycol monohexyl ether, ethylene glycol monophenyl 15 ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monobutyl ether, diethylene glycol monoisobutyl ether, diethylene glycol monohexyl ether, 20 diethylene glycol monophenyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monoisopropyl ether, propylene glycol monobutyl ether, propylene glycol monoisobutyl ether, propylene glycol 25 monophenyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monoisopropyl ether, dipropylene glycol monobutyl ether, dipropylene 104 glycol monoisobutyl ether, dipropylene glycol monophenyl ether, etc.; diols such as ethylene glycol, diethylene glycol, triethylene glycol, 1,3-propanediol, 1,2-propanediol, propylene glycol, dipropylene glycol, 5 tripropylene glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, hexylene glycol, 1,9-nonanediol, neopentyl glycol, methylpentanediol, etc.; aliphatic polyols such as glycerin, castor oil, trimethylol propane, trimethylolethane, hexanetriol, pentaery 10 thritol, a-methyl glucoside, sorbitol, sucrose, etc.; polyols such as polyethylene glycols, polypropylene glycols, polytetramethylene glycols, adipate-derived polyols, epoxy-modified polyols, polyether ester polyols, polycarbonate polyols, polycaprolactone diols, 15 amine-modified polyols, polyether polyols obtained by adding one of or a mixture of two or more of alkylene oxides (e.g. ethylene oxide and propylene oxide) to one of or a mixture of two or more of polyhydric alcohols (glycerin and propylene glycol), acryl polyols, 20 fluorinated polyols, polybutadiene polyols, polyhydroxy polyols, castor oil-derived polyols, polymer polyols, halogen-containing polyols, phosphorus-containing polyols, etc.; and alkanolamines such as N,N-dialkyl ethanolamines, N,N-dialkylisopropanolamines, N 25 alkyldiethanolamines, N-alkyldiisopropanolamines, triethanolamine, triisopropanolamine, N,N,N',N' tetrakis(2-hydroxyethyl)ethylenediamine, N,N,N',N' tetrakis(2-hydroxypropyl)ethylenediamine, etc.
105 Of the above-exemplified alcohol compounds, aliphatic alcohols having 10 or less carbon atoms, the glycol ethers, the diols, the aliphatic polyols, polyols having a molecular weight of 2,000 or less, and 5 the alkanolamines are preferable. The above-exemplified alcohol compounds may be used singly or in combination, and the above exemplified phenolic compounds may also be used singly or in combination. 10 As the amino compound that is reacted with the polyisocyanate compound to form one or more urea groups, any compound may be used so long as it has one or more amino groups bonded to carbon atoms, respec tively. The amino compound includes, for example, 15 aromatic amines such as aniline, o-toluidine, m toluidine, p-toluidine, o-anisidine, p-anisidine, p phenetidine, N,N-dimethyl-p-phenylenediamine, N,N diethyl-p-phenylenediamine, 2,4-dimethoxyaniline, 2,5 dimethoxyaniline, 3,4-dimethoxyaniline, p-amino 20 acetanilide, p-aminobenzoic acid, o-aminophenol, m aminophenol, p-aminophenol, 2,3-xylidine, 2,4-xylidine, 3,4-xylidine, 2,6-xylidine, 4-aminobenzonitrile, anthranilic acid, p-cresidine, 2,5-dichloroaniline, 2,6-dichloroaniline, 3,4-dichloroaniline, 3,5 25 dichloroaniline, 2,4,5-trichloroaniline, a-naphthyl amine, aminoanthracene, o-ethylaniline, o-chloro aniline, m-chloroaniline, p-chloroaniline, N-methyl aniline, N-ethylaniline, N-propylaniline, N-butyl- 106 aniline, N,N-diglycidylaniline, N,N-diglycidyl-o toluidine, acetoacetic acid anilide, trimethylphenyl ammonium bromide, 4,4'-diamino-3,3'-diethyldiphenyl methane, 4,4'-diaminobenzanilide, 3,5-diaminochloro 5 benzene, diaminodiphenyl ether, 3,3'-dichloro-4,4' diaminodiphenylmethane, 3,3'-dimethyl-4,4' diaminodiphenylmethane, tolidine base, o-phenylene diamine, m-phenylenediamine, p-phenylenediamine, 2 chloro-p-phenylenediamine, dianisidine, methyl p 10 aminobenzoate, ethyl p-aminobenzoate, n-propyl p aminobenzoate, isopropyl p-aminobenzoate, butyl p aminobenzoate, dodecyl p-aminobenzoate, benzyl p aminobenzoate, o-aminobenzophenone, m-aminoaceto phenone, p-aminoacetophenone, m-aminobenzamide, o 15 aminobenzamide, p-aminobenzamide, p-amino-N-methyl benzamide, 3-amino-4-methylbenzamide, 3-amino-4 methoxybenzamide, 3-amino-4-chlorobenzamide, p-(N phenylcarbamoyl)aniline, p-[N-(4-chlorophenyl) carbamoyl]aniline, p-[N-(4-aminophenyl)carbamoyl] 20 aniline, 2-methoxy-5-(N-phenylcarbamoyl)aniline, 2 methoxy-5-[N-(2'-methyl-3'-chlorophenyl)carbamoyl] aniline, 2-methoxy-5-[N-(2'-chlorophenyl)carbamoyl] aniline, 5-acetylamino-2-methoxyaniline, 4-acetylamino aniline, 4-(N-methyl-N-acetylamino)aniline, 2,5 25 diethoxy-4-(N-benzoylamino)aniline, 2,5-dimethoxy-4-(N benzoylamino)aniline, 2-methoxy-4-(N-benzoylamino)-5 methylaniline, 4-sulfamoylaniline, 3-sulfamoylaniline, 2-(N-ethyl-N-phenylaminosulfonyl)aniline, 4-dimethyl- 107 aminosulfonylaniline, 4-diethylaminosulfonylaniline, sulfathiazole, 4-aminodiphenyl sulfone, 2-chloro-5-N phenylsulfamoylaniline, 2-methoxy-5-N,N-diethyl sulfamoylaniline, 2,5-dimethoxy-4-N-phenysulfamoyl 5 aniline, 2-methoxy-5-benzylsulfonylaniline, 2 phenoxysulfonylaniline, 2-(2'-chlorophenoxy)sulfonyl aniline, 3-anilinosulfonyl-4-methylaniline, bis[4-(m aminophenoxy)phenyl] sulfone, bis[4-(p-aminophenoxy) phenyl] sulfone, bis[3-methyl-4-(p-aminophenoxy)phenyl] 10 sulfone, 3,3'-dimethoxy-4,4'-diaminobiphenyl, 3,3' dimethyl-4,4'-diaminobiphenyl, 2,2'-dichloro-4,4' diamino-5,5'-dimethoxybiphenyl, 2,2',5,5'-tetrachloro 4,4'-diaminobiphenyl, o-tolidine sulfone, 2,4' diaminobiphenyl, 2,2'-diaminobiphenyl, 4,4'-diamino 15 biphenyl, 2,2'-dichloro-4,4'-diaminobiphenyl, 3,3' dichloro-4,4'-diaminobiphenyl, 2,2'-dimethyl-4,4' diaminobiphenyl, 4,4'-thiodianiline, 2,2' dithiodianiline, 4,4'-dithiodianiline, 4,4' diaminodiphenyl ether, 3,3'-diaminodiphenyl ether, 20 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl methane, 3,4'-diaminodiphenylmethane, bis(3-amino-4 chlorophenyl) sulfone, bis(3,4-diaminophenyl) sulfone, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfone, 3,3'-diamino 25 diphenylmethane, 4,4-diaminodiphenylamine, 4,4' ethylenedianiline, 4,4'-diamino-2,2'-dimethyldibenzyl, 3,3'-diaminobenzophenone, 4,4'-diaminobenzophenone, 1,4-bis(4-aminophenoxy)benzene, 1,3-bis(4-amino- 108 phenoxy)benzene, 1,3-bis(3-aminophenoxy)benzene, 9,9 bis(4-aminophenyl)fluorene, 2,2-bis(4-aminophenoxy phenyl)propane, 4,4'-bis(4-aminophenoxy)diphenyl, 3,3',4,4'-tetraaminodiphenyl ether, 3,3',4,4' 5 tetraaminodiphenyl sulfone, 3,3',4,4'-tetraamino benzophenone, 3-aminobenzonitrile, 4-phenoxyaniline, 3 phenoxyaniline, 4,4'-methylenebis-o-toluidine, 4,4'-(p phenyleneisopropylidene)-bis-(2,6-xylidine), o-chloro p-nitroaniline, o-nitro-p-chloroaniline, 2,6-dichloro 10 4-nitroaniline, 5-chloro-2-nitroaniline, 2-amino-4 chlorophenol, o-nitroaniline, m-nitroaniline, p nitroaniline, 2-methyl-4-nitroaniline, m-nitro-p toluidine, 2-amino-5-nitrobenzonitrile, Metol, 2,4 diaminophenol, N-(f-hydroxyethyl)-o-aminophenol 15 sulfate, sulfanilic acid, metanilic acid, 4B acid, C acid, 2B acid, p-fluoroaniline, o-fluoroaniline, 3 chloro-4-fluoroaniline, 2,4-difluoroaniline, 2,3,4 trifluoroaniline, m-aminobenzotrifluoride, m toluylenediamine, 2-aminothiophenol, 2-amino-3-bromo-5 20 nitrobenzonitrile, diphenylamine, p-aminodiphenylamine, octylated diphenylamine, 2-methyl-4-methoxydiphenyl amine, N,N-diphenyl-p-phenylenediamine, dianisidine, 3,3'-dichlorobenzidine, 4,4'-diaminostilbene-2,2' disulfonic acid, benzylethylaniline, 1,8-naphthalene 25 diamine, sodium naphthionate, Tobias acid, H acid, J acid, phenyl J acid, 1,4-diamino-anthraquinone, 1,4 diamino-2,3-dichloroanthraquinone, etc.; heterocyclic compound amines such as 3-amino-1,2,4-triazole, 2- 109 aminopyridine, 3-aminopyridine, 4-aminopyridine, cx amino- E -caprolactam, acetoguanamine, 2,4-diamino-6-[2' methylimidazolyl-(1)]ethyl-S-triazine, 2,3-diamino pyridine, 2,5-diaminopyridine, 2,3,5-triaminopyridine, 5 1-amino-4-methylpiperazine, 1-(2-aminoethyl)piperazine, bis(aminopropyl)piperazine, N-(3-aminopropyl) morpholine, etc.; and aliphatic amines such as methylamine, ethylamine, dimethylamine, diethylamine, stearylamine, allylamine, diallylamine, isopropylamine, 10 diisopropylamine, 2-ethylhexylamine, ethanolamine, 3 (2-ethylhexyloxy)propylamine, 3-ethoxypropylamine, diisobutylamine, 3-(diethylamino)propylamine, di-2 ethylhexylamine, 3-(dibutylamino)propylamine, t butylamine, propylamine, 3-(methylamino)propylamine, 3 15 (dimethylamino)propylamine, 3-methoxypropylamine, methylhydrazine, 1-methylbutylamine, methanediamine, 1,4-diaminobutane, cyclohexanemethylamine, cyclohexyl amine, 4-methylcyclohexylamine, 2-bromoethylamine, 2 methoxyethylamine, 2-ethoxymethylamine, 2-amino-1 20 propanol, 2-aminobutanol, 3-amino-1,2-propanediol, 1,3 diamino-2-hydroxypropane, 2-aminoethanethiol, ethylene diamine, diethylenetriamine, hexamethylenediamine, etc. In addition, of the above-exemplified amino compounds, the aromatic amines are preferable, and 25 aniline derivatives having at least one amino group and represented by the following formula (z) or (VIII) are especially preferable: 110 R -NH2 (Z) R2 wherein R 1 and R 2 are independently a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or an amino group; or R, X, X2 R 3 R R3 (VIII) R2 R4 wherein R 1 , R 2 , R 3 and R 4 are independently a hydrogen 5 atom, a halogen atom, an alkyl group, an alkoxy group or an amino group, X 1 and X 2 are independently an amino group or a group represented by the formula (b): -- Oa NH2 (b) and Yi is any of -S0 2 -, -0-, - (S) n-, - (CH2) n-, -CO-, -CONH-, -NH-, -CH (COOR 1 ) -, -C (CF 3 )2-, -CR 2
R
3 - and a group 10 represented by any of the formulas (a): 111 O O CH
CH
3 --- -- Q -o- (a)
CH
3
CH
3 -- O O- - -(a O 0 L II -0o 0 or is absent, each of R 1 , R 2 and R 3 is an alkyl group, and n is 1 or 2. Such amine compounds may be used singly or in combination. 5 The urea-urethane compound used as a developer in each of the twenty-first and twenty-second aspects of the present invention refers to a compound 112 having at least one urea group (-NHCONH- group) and at least one urethane group (-NHCOO- group) in the molecule. It has been known that compounds having one 5 or more urea groups have color-developing effect, but they have not been practical because they give a low coloring density and have an insufficient shelf stability. However, surprisingly, a urea-urethane compound having at least one urea group and at least 10 one urethane group in the molecule is an excellent developer for a colorless or light-colored dye precursor, and a color-producing composition comprising the urea-urethane compound and the dye precursor and a recording material obtained by using the color 15 producing composition give a high coloring density and have an excellent shelf stability. Although a mechanism by which such a urea urethane compound exhibits an excellent color developing effect is unknown, it is conjectured that 20 the effect is due to the interaction between the urea group(s) and the urethane group(s) in the molecule. As the urea-urethane compound used as developer in each of the twenty-first and twenty-second aspects of the present invention, any compound may be 25 used so long as it has both at least one urea group (-NHCONH- group) and at least one urethane group (-NHCOO- group) in the molecule. The urea-urethane compound is preferably an aromatic compound or a 113 heterocyclic compound. In addition, the urea-urethane compound is preferably a compound in which an aromatic compound residue or heterocyclic compound residue is directly bonded to each end of each of the urea 5 group(s) and the urethane group(s). It is more prefer able that besides the urea group(s) (-NHCONH- group(s)) and urethane group(s) (-NHCOO- group(s)), one or more sulfonic acid groups (-SO 2 - groups), amide groups (-NHCO- groups) or isopropylidene groups (-C(CH 3
)
2 10 groups) be present in the molecule without binding directly to the urea group(s). The molecular weight of the urea-urethane compound is preferably 5,000 or less, more preferably 2,000 or less. The total number of urea group(s) and 15 urethane group(s) in the urea-urethane compound is preferably 20 or less, more preferably 10 or less. The ratio of urea group(s) to urethane group(s) in the molecular structure of the urea-urethane compound is preferably 1 : 3 to 3 : 1, in particular, 1 : 2 to 2 20 1. When used in a heat-sensitive recording material, the urea-urethane compound is preferably one that has a melting point. The melting point ranges preferably from 40 0 C to 500*C, in particular, from 60 0 C 25 to 300 0 C. A process for synthesizing the urea-urethane compound used as developer in each of the twenty-first and twenty-second aspects of the present invention is 114 not particularly limited so long as at least one urea group (-NHCONH- group) and at least one urethane group (-NHCOO- group) are formed. A process in which the urea-urethane compound is produced by the reaction of 5 an isocyanate compound with an OH group-containing compound and an amine compound is preferable because of its ease. In detail, in the case of the urea-urethane compound used as developer in the present invention, an 10 isocyanate having at least two isocyanate groups is used as a starting material and one or more urethane groups are formed by reacting all the isocyanate groups except at least one with an OH group-containing compound, after which one or more urea groups can be 15 formed by reacting the remaining isocyanate group(s) with an amine compound. It is also possible to form one or more urea groups by reacting all the isocyanate groups except at least one with an amine compound at first, and then form one or more urethane groups by 20 reacting the remaining isocyanate group(s) with an OH group-containing compound. The starting isocyanate is not particularly limited so long as it has two or more isocyanate groups. The starting isocyanate includes, for example, 25 p-phenylene diisocyanate, 2,5-dimethoxybenzene-1,4 diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, diphenylmethane diisocyanate, o-tolidine diisocyanate, diphenyl ether diisocyanate, 1,5- 115 naphthylene diisocyanate, dianisidine diisocyanate, 9 ethylcarbazole-3,6-diisocyanate, 3,3'-dimethyl-4,4' diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, triphenylmethane 5 triisocyanate, tris(4-phenylisocyanato)thiophosphate, 4,4',4"-triisocyanato-2,5-dimethoxytriphenylamine, 4,4', 4 "-triisocyanatotriphenylamine, m-xylylene diisocyanate, lysine diisocyanate, dimer acid diisocyanate, isopropylidene bis-4-cyclohexyl 10 isocyanate, dicyclohexylmethane diisocyanate and methylcyclohexane diisocyanate. As the starting isocyanate, there may also be used diisocyanate dimers such as N,N'-(4,4'-dimethyl-3,3'-diphenyldiiso cyanato)urethodione (Desmodule TT, a trade name), a 15 toluene diisocyanate dimer; and diisocyanate trimers such as 4,4',4"-trimethyl-3,3',3"-triisocyanato-2,4,6 triphenylcyanurate. There may also be used water adduct isocyanates of toluene diisocyanate, diphenyl methane diisocyanate and the like, such as 1,3-bis(3 20 isocyanato-4-methylphenyl)urea; polyol adducts such as trimethylolpropane adduct of toluene diisocyanate (Desmodule L, a trade name); and amine adducts. There may also be used compounds having two or more isocyanate groups, among the isocyanate compounds and 25 isocyanate adduct compounds described in the specifi cation of JP-A-8-225445 and the specification of JP-A 8-250623. Especially preferable examples of the 116 starting isocyanate are toluene diisocyanates. Of the toluene diisocyanates, 2.4-toluene diisocyanate is preferable. Besides 2.4-toluene diisocyanate, mixtures of 2.4-toluene diisocyanate and 2,6-toluene 5 diisocyanate are generally on the market and available at a low price and may also be used as the staring isocyanate. As the amine compound that is reacted with the starting isocyanate for the urea-urethane compound 10 as developer to form one or more urea groups, any compound may be used so long as it has one or more amino groups. The amine compound includes, for example, aromatic amines such as aniline, o-toluidine, m-toluidine, p-toluidine, o-anisidine, p-anisidine, p 15 phenetidine, N,N-dimethylaniline, N,N-diethylaniline, N,N-dimethyl-p-phenylenediamine, N,N-diethyl-p phenylenediamine, 2,4-dimethoxyaniline, 2,5-dimethoxy aniline, 3,4-dimethoxyaniline, p-aminoacetanilide, p aminobenzoic acid, o-aminophenol, m-aminophenol, p 20 aminophenol, 2,3-xylidine, 2,4-xylidine, 3,4-xylidine, 2,6-xylidine, 4-aminobenzonitrile, anthranilic acid, p cresidine, 2,5-dichloroaniline, 2,6-dichloroaniline, 3,4-dichloroaniline, 3,5-dichloroaniline, 2,4,5 trichloroaniline, a-naphthylamine, aminoanthracene, o 25 ethylaniline, o-chloroaniline, m-chloroaniline, p chloroaniline, N-methylaniline, N-ethylaniline, N propylaniline, N-butylaniline, N,N-diglycidylaniline, N,N-diglycidyl-o-toluidine, acetoacetic acid anilide, 117 trimethylphenylammonium bromide, 4,4'-diamino-3,3' diethyldiphenylmethane, 4,4'-diaminobenzanilide, 3,5 diaminochlorobenzene, diaminodiphenyl ether, 3,3' dichloro-4,4'-diaminodiphenylmethane, 3,3'-dimethyl 5 4,4'-diaminodiphenylmethane, tolidine base, o phenylenediamine, m-phenylenediamine, p-phenylene diamine, 2-chloro-p-phenylenediamine, dianisidine, methyl p-aminobenzoate, ethyl p-aminobenzoate, n-propyl p-aminobenzoate, isopropyl p-aminobenzoate, butyl p 10 aminobenzoate, dodecyl p-aminobenzoate, benzyl p aminobenzoate, o-aminobenzophenone, m-aminoaceto phenone, p-aminoacetophenone, m-aminobenzamide, o aminobenzamide, p-aminobenzamide, p-amino-N-methyl benzamide, 3-amino-4-methylbenzamide, 3-amino-4 15 methoxybenzamide, 3-amino-4-chlorobenzamide, p-(N phenylcarbamoyl)aniline, p-[N-(4-chlorophenyl) carbamoyl]aniline, p-[N-(4-aminophenyl)carbamoyll aniline, 2-methoxy-5-(N-phenylcarbamoyl)aniline, 2 methoxy-5-[N-(2'-methyl-3'-chlorophenyl)carbamoyl] 20 aniline, 2-methoxy-5-[N-(2'-chlorophenyl)carbamoyl] aniline, 5-acetylamino-2-methoxyaniline, 4-acetylamino aniline, 4-(N-methyl-N-acetylamino)aniline, 2,5 diethoxy-4-(N-benzoylamino)aniline, 2,5-dimethoxy-4-(N benzoylamino)aniline, 2-methoxy-4-(N-benzoylamino)-5 25 methylaniline, 4-sulfamoylaniline, 3-sulfamoylaniline, 2-(N-ethyl-N-phenylaminosulfonyl)aniline, 4-dimethyl aminosulfonylaniline, 4-diethylaminosulfonylaniline, sulfathiazole, 4-aminodiphenyl sulfone, 2-chloro-5-N- 118 phenylsulfamoylaniline, 2-methoxy-5-N,N-diethyl sulfamoylaniline, 2,5-dimethoxy-4-N-phenysulfamoyl aniline, 2-methoxy-5-benzylsulfonylaniline, 2 phenoxysulfonylaniline, 2-(2'-chlorophenoxy)sulfonyl 5 aniline, 3-anilinosulfonyl-4-methylaniline, bis[4-(m aminophenoxy)phenyl] sulfone, bis[4-(p-aminophenoxy) phenyll sulfone, bis[3-methyl-4-(p-aminophenoxy)phenyl] sulfone, 3,3'-dimethoxy-4,4'-diaminobiphenyl, 3,3' dimethyl-4,4'-diaminobiphenyl, 2,2'-dichloro-4,4' 10 diamino-5,5'-dimethoxybiphenyl, 2,2',5,5'-tetrachloro 4,4'-diaminobiphenyl, o-tolidine sulfone, 2,4' diaminobiphenyl, 2,2'-diaminobiphenyl, 4,4'-diamino biphenyl, 2,2'-dichloro-4,4'-diaminobiphenyl, 3,3' dichloro-4,4'-diaminobiphenyl, 2,2'-dimethyl-4,4' 15 diaminobiphenyl, 4,4'-thiodianiline, 2,2' dithiodianiline, 4,4'-dithiodianiline, 4,4' diaminodiphenyl ether, 3,3'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl methane, 3,4'-diaminodiphenylmethane, bis(3-amino-4 20 chlorophenyl) sulfone, bis(3,4-diaminophenyl) sulfone, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfone, 3,3'-diamino diphenylmethane, 4,4-diaminodiphenylamine, 4,4' ethylenedianiline, 4,4'-diamino-2,2'-dimethyldibenzyl, 25 3,3'-diaminobenzophenone, 4,4'-diaminobenzophenone, 1,4-bis(4-aminophenoxy)benzene, 1,3-bis(4-amino phenoxy)benzene, 1,3-bis(3-aminophenoxy)benzene, 9,9 bis(4-aminophenyl)fluorene, 2,2-bis(4-aminophenoxy- 119 phenyl)propane, 4,4'-bis(4-aminophenoxy)diphenyl, 3,3',4,4'-tetraaminodiphenyl ether, 3,3',4,4' tetraaminodiphenyl sulfone, 3,3',4,4'-tetraamino benzophenone, 3-aminobenzonitrile, 4-phenoxyaniline, 3 5 phenoxyaniline, 4,4'-methylenebis-o-toluidine, 4,4'-(p phenyleneisopropylidene)-bis-(2,6-xylidine), o-chloro p-nitroaniline, o-nitro-p-chloroaniline, 2,6-dichloro 4-nitroaniline, 5-chloro-2-nitroaniline, 2-amino-4 chlorophenol, o-nitroaniline, m-nitroaniline, p 10 nitroaniline, 2-methyl-4-nitroaniline, m-nitro-p toluidine, 2-amino-5-nitrobenzonitrile, Metol, 2,4 diaminophenol, N-(-hydroxyethyl)-o-aminophenol sulfate, sulfanilic acid, metanilic acid, 4B acid, C acid, 2B acid, p-fluoroaniline, o-fluoroaniline, 3 15 chloro-4-fluoroaniline, 2,4-difluoroaniline, 2,3,4 trifluoroaniline, m-aminobenzotrifluoride, m-toluylene diamine, 2-aminothiophenol, 2-amino-3-bromo-5 nitrobenzonitrile, diphenylamine, p-aminodiphenylamine, octylated diphenylamine, 2-methyl-4-methoxydiphenyl 20 amine, N,N-diphenyl-p- phenylenediamine, dianisidine, 3,3'-dichlorobenzidine, 4,4'-diaminostilbene-2,2' disulfonic acid, benzylethylaniline, 1,8-naphthalene diamine, sodium naphthionate, Tobias acid, H acid, J acid, phenyl J acid, 1,4-diamino-anthraquinone, 1,4 25 diamino-2,3-dichloroanthraquinone, etc.; heterocyclic compound amines such as 3-amino-1,2,4-triazole, 2 aminopyridine, 3-aminopyridine, 4-aminopyridine, a amino-s-caprolactam, acetoguanamine, 2,4-diamino-6-[2'- 120 methylimidazolyl-(1)]ethyl-S-triazine, 2,3-diamino pyridine, 2,5-diaminopyridine, 2,3,5-triaminopyridine, 1-amino-4-methylpiperazine, 1-(2-aminoethyl)piperazine, bis (aminopropyl)piperazine, N- (3-aminopropyl) 5 morpholine, etc.; and aliphatic amines such as methyl amine, ethylamine, dimethylamine, diethylamine, stearylamine, allylamine, diallylamine, isopropylamine, diisopropylamine, 2-ethylhexylamine, ethanolamine, 3 (2-ethylhexyloxy) propylamine, 3-ethoxypropylamine, 10 diisobutylamine, 3-(diethylamino)propylamine, di-2 ethylhexylamine, 3-(dibutylamino)propylamine, t butylamine, propylamine, 3-(methylamino)propylamine, 3 (dimethylamino)propylamine, 3-methoxypropylamine, methylhydrazine, 1-methylbutylamine, methanediamine, 15 1,4-diaminobutane, cyclohexanemethylamine, cyclohexyl amine, 4-methylcyclohexylamine, 2-bromoethylamine, 2 methoxyethylamine, 2-ethoxymethylamine, 2-amino-1 propanol, 2-aminobutanol, 3-amino-1,2-propanediol, 1,3 diamino-2-hydroxypropane, 2-aminoethanethiol, ethylene 20 diamine, diethylenetriamine, hexamethylenediamine, etc. Of the above-exemplified amine compounds, aniline derivatives having at least one amino group and represented by the following formula (VIII) are especially preferable:
R
1
X
1
X
2
R
3 Y1 (VIII) R 2 R4 121 wherein R 1 , R 2 , R 3 and R 4 are independently a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or an amino group, X, and X 2 are independently an amino group or a group represented by the formula (b): -- ONH2 (b) 5 and Yj is any of -S0 2 -, -0-, -(S) -, -(CH 2 )n-, -CO-, -CONH- and a group represented by any of the formulas (a): 122
CH
3 -- OQ O -0-0C
CH
3 - - - - O --- ( a)
CH
3
CH
3 O 0 L II -o ci 0 or is absent, and n is 1 or 2. As the OH group-containing compound that is reacted with the isocyanate to form one or more urethane groups, any compound may be used so long as it 5 contains one or more OH groups. The OH group containing compound includes, for example, phenols such as phenol, cresol, xylenol, p-ethylphenol, o-isopropyl- 123 phenol, resorcinol, p-tert-butylphenol, p-tert octylphenol, 2-cyclohexylphenol, 2-allylphenol, 4 indanol, thymol, 2-naphthol, p-nitrophenol, o-chloro phenol, p-chlorophenol, 2,2-bis(4-hydroxyphenyl) 5 propane, 2,2-bis(hydroxyphenyl)butane, 2,2-bis(hydroxy phenyl)pentane, 2,2-bis(hydroxyphenyl)heptane, catechol, 3-methylcatechol, 3-methoxycatechol, pyrogallol, hydroquinone, methylhydroquinone, 4 phenylphenol, p,p'-biphenol, 4-cumylphenol, butyl 10 bis(4-hydroxyphenyl)acetate, benzyl bis(4-hydroxy phenyl)acetate, bis(4-hydroxyphenyl) sulfone, bis(3 methyl-4-hydroxyphenyl) sulfone, bis(3,5-dimethyl-4 hydroxyphenyl) sulfone, 4-hydroxyphenyl-4'-methylphenyl sulfone, 3-chloro-4-hydroxyphenyl-4'-methylphenyl 15 sulfone, 3,4-dihydroxyphenyl-4'-methylphenyl sulfone, 4-isopropyloxyphenyl-4'-hydroxyphenyl sulfone, bis(2 allyl-4-hydroxyphenyl) sulfone, 4-hydroxyphenyl-4' benzyloxyphenyl sulfone, 4-isopropylphenyl-4' hydroxyphenyl sulfone, 4-hydroxy-4'-isopropoxydiphenyl 20 sulfone, bis(2-methyl-3-tert-butyl-4-hydroxyphenyl) sulfide, 4,4'-dihydroxydiphenyl ether, 4,4' thiodiphenol, 4,4'-dihydroxybenzophenone, 2,2-bis(4 hydroxyphenyl)hexafluoropropane, 4,4'-dihydroxy diphenylmethane, 3,3'-dihydroxydiphenylamine, bis(4 25 hydroxy-3-methylphenyl) sulfide, bis(4-(2-hydroxy) phenyl) sulfone, 2,4-dihydroxybenzophenone, 2,2',4,4' tetrahydroxybenzophenone, phenyl salicylate, salicylanilide, methyl 4-hydroxybenzoate, benzyl 4- 124 hydroxybenzoate, (4'-chlorobenzyl) 4-hydroxybenzoate, ethyl 1,2-bis(4'-hydroxybenzoate), pentyl 1,5-bis(4' hydroxybenzoate), hexyl 1,6-bis(4'-hydroxybenzoate), dimethyl 3-hydroxyphthalate, stearyl gallate, lauryl 5 gallate, methyl gallate, 4-methoxyphenol, 4 (benzyloxy)phenol, 4-hydroxybenzaldehyde, 4-n octyloxysalicylic acid, 4-n-butyloxysalicylic acid, 4 n-pentyloxysalicylic acid, 3-n-dodecyloxysalicylic acid, 3-n-octanoyloxysalicylic acid, 4-n-octyloxy 10 carbonylaminosalicylic acid, 4-n-octanoyloxycarbonyl aminosalicylic acid, etc. However, as such phenols, those having an amino group are not desirable. Since the amino group has a higher reactivity towards an isocyanate group than does an OH group, the amino group 15 reacts with the isocyanate group before the OH group, so that it is difficult in some cases to obtain the desired compound. The OH group-containing compound also includes alcohols such as methanol, ethanol, propanol, 20 butanol, pentanol, hexanol, heptanol, octanol, isopropanol, iosbutanol, isopentanol, 2-ethyl-1 hexanol, 1-decanol, 2-pentanol, 3-hexanol, tert butanol, tert-amyl alcohol, methyl Cellosolve, butyl Cellosolve, methyl Carbitol, allyl alcohol, 2-methyl-2 25 propen-1-ol, benzyl alcohol, 4-pyridinemethanol, phenyl Cellosolve, furfuryl alcohol, cyclohexanol, cyclohexyl methanol, cyclopentanol, 2-chloroethanol, 1-chloro-3 hydroxypropane, glycerin, glycerol, etc.; polyether 125 type polyols such as polypropylene glycols, polytetra methylene ether glycols, adipate-derived polyols, epoxy-modified polyols, polyether ester polyols, polycarbonate polyols, polycaprolactone diols, phenolic 5 polyols, amine-modified polyols, etc.; and polyols such as ethylene glycol, diethylene glycol, 1,3-propanediol, 1,2-propanediol, propylene glycol, dipropylene glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,6 hexane glycol, 1,9-nonanediol, acryl polyols, fluoro 10 carbon polyols, polybutadiene polyols, polyhydroxy polyols, trimethylolpropane, trimethylolethane, hexanetriol, phosphoric acid, neopentyl glycol, pentaerythritol, castor-oil-derived polyols, polymer polyols, methylpentanediol, halogen-containing polyols, 15 phosphorus-containing polyols, ethylenediamine, a methylglucoside, sorbitol, sucrose, etc. The urea-urethane compound used as developer in each of the twenty-first and twenty-second aspects of the present invention is preferably a urea-urethane 20 compound having a molecular structure in which the number of urea groups (A) and the number of urethane groups (B) satisfy the following numeral formula: 10 (A + B) 3 wherein each of A and B is an integer of 1 or more. 25 The urea-urethane compound in which the number of urea groups (A) and the number of urethane 126 groups (B) satisfy the numeral formula 10 > (A + B) > 3 (wherein each of A and B is an integer of 1 or more) is a compound having a molecular structure in which at least one urea group (-NHCONH- group) and at least one 5 urethane group (-NHCOO- group) are present in a total number of not more than 10 and not less than 3. Such a compound has not been reported and is quite novel. This novel compound is useful in the case of recording materials which use a recording energy 10 such as heat, pressure or the like. A process for synthesizing the urea-urethane compound in which the number of urea groups (A) and the number of urethane groups (B) satisfy the numeral formula 10 (A + B) L 3 (wherein each of A and B is 15 an integer of 1 or more) is not particularly limited so long as at least one urea group (-NHCONH- group) and at least one urethane group (-NHCOO- group) are formed in a total number of 3 to 10. A process in which the urea-urethane compound is produced by the reaction of 20 an isocyanate compound with an OH group-containing compound and an amine compound is preferable because of its ease. In detail, as the urea-urethane compound used as developer in each of the twenty-first and twenty 25 second aspects of the present invention, a urea urethane compound having at least one urea group and at least one urethane group in a total number of at least 3 can be obtained, for example, by using an isocyanate 127 having at least two isocyanate groups, as a starting material, reacting all the isocyanate groups except at least one with an OH group-containing compound to form one or more urethane groups, and then reacting the 5 remaining isocyanate groups of two molecules of the resulting urethane compound with each other by the use of water to bond them to each other. In addition, a urea-urethane compound having at least one urea group and at least one urethane group 10 in a total number of at least 3 can be obtained, for example, by using an isocyanate having at least two isocyanate groups, as a starting material, reacting all the isocyanate groups except at least one with an OH group-containing compound to form one or more urethane 15 groups, reacting the remaining isocyanate group(s) with an amine compound having two or more amino groups, to form one or more urea groups, and reacting the remaining amino group(s) with an isocyanate compound. Furthermore, a urea-urethane compound having 20 at least one urea group and at least one urethane group in a total number of at least 3 can be obtained also by reacting all the isocyanate groups except at least one with an amine compound at first to form one or more urea groups, reacting the remaining isocyanate group(s) 25 with a compound containing two or more OH groups, to form one or more urethane groups, and then reacting the resulting compound with an isocyanate compound. In this case, a urea-urethane compound having at least one 128 urea group and at least one urethane group in a total number of 3 to 10 can be obtained by using an isocyanate compound having two or more isocyanate groups, as the isocyanate to be lastly reacted, and 5 repeating a procedure of reacting the remaining isocyanate group(s) with a compound containing two or more OH groups or an amino compound having two or more amino groups. The starting isocyanate is not particularly 10 limited so long as it has two or more isocyanate groups. The starting isocyanate includes, for example, p-phenylene diisocyanate, 2,5-dimethoxybenzene-1,4 diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, diphenylmethane diisocyanate, o-tolidine 15 diisocyanate, diphenyl ether diisocyanate, 1,5 naphthylene diisocyanate, dianisidine diisocyanate, 9 ethylcarbazole-3,6-diisocyanate, 3,3'-dimethyl-4,4' diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, triphenylmethane 20 triisocyanate, tris(4-phenylisocyanate) thiophosphate, 4,4',4"-triisocyanato-2,5-dimethoxytriphenylamine, 4,4',4"-triisocyanatotriphenylamine, m-xylylene diisocyanate, lysine diisocyanate, dimer acid diisocyanate, isopropylidene bis-4-cyclohexyl 25 isocyanate, dicyclohexylmethane diisocyanate and methylcyclohexane diisocyanate. As the starting isocyanate, there may also be used diisocyanate dimers such as N,N'-(4,4'-dimethyl- 129 3
,
3 '-diphenyldiisocyanato)urethodione (Desmodule TT, a trade name), a toluene diisocyanate dimer; and diisocyanate trimers such as 4,4',4"-trimethyl-3,3',3" triisocyanato-2,4,6-triphenylcyanurate. There may also 5 be used water adduct isocyanates of toluene diiso cyanate, diphenylmethane diisocyanate and the like, such as 1,3-bis( 3 -isocyanato-4-methylphenyl)urea; polyol adducts such as trimethylolpropane adduct of toluene diisocyanate (Desmodule L, a trade name); and 10 amine adducts. There may also be used compounds having two or more isocyanate groups, among the isocyanate compounds and isocyanate adduct compounds described in the specification of JP-A-10-76757 and the specifica tion of JP-A-10-95171 (the contents of these references 15 are hereby incorporated herein by reference). Especially preferable examples of the starting isocyanate are toluene diisocyanates. Of the toluene diisocyanates, 2.4-toluene diisocyanate is preferable. Besides 2.4-toluene diisocyanate, mixtures 20 of 2.4-toluene diisocyanate and 2,6-toluene diiso cyanate are generally on the market and available at a low price and may also be used as the staring isocyanate. The mixtures of these toluene diisocyanate isomers are liquid at ordinary temperatures. 25 As the amine compound that is reacted with the starting isocyanate for the urea-urethane compound to form one or more urea groups, any compound may be used so long as it has one or more amino groups. The 130 amine compound includes, for example, aromatic amines such as aniline, o-toluidine, m-toluidine, p-toluidine, o-anisidine, p-anisidine, p-phenetidine, N,N-dimethyl aniline, N,N-diethylaniline, N,N-dimethyl-p-phenylene 5 diamine, N,N-diethyl-p-phenylenediamine, 2,4-dimethoxy aniline, 2,5-dimethoxyaniline, 3,4-dimethoxyaniline, p aminoacetanilide, p-aminobenzoic acid, o-aminophenol, m-aminophenol, p-aminophenol, 2,3-xylidine, 2,4 xylidine, 3,4-xylidine, 2,6-xylidine, 4-aminobenzo 10 nitrile, anthranilic acid, p-cresidine, 2,5-dichloro aniline, 2,6-dichloroaniline, 3,4-dichloroaniline, 3,5 dichloroaniline, 2 ,4,5-trichloroaniline, a-naphthyl amine, aminoanthracene, o-ethylaniline, o-chloro aniline, m-chloroaniline, p-chloroaniline, N-methyl 15 aniline, N-ethylaniline, N-propylaniline, N-butyl aniline, N,N-diglycidylaniline, N,N-diglycidyl-o toluidine, acetoacetic acid anilide, trimethylphenyl ammonium bromide, 4,4'-diamino-3,3'-diethyldiphenyl methane, 4,4'-diaminobenzanilide, 3,5-diaminochloro 20 benzene, diaminodiphenyl ether, 3,3'-dichloro-4,4' diaminodiphenylmethane, 3,3'-dimethyl-4,4' diaminodiphenylmethane, tolidine base, o-phenylene diamine, m-phenylenediamine, p-phenylenediamine, 2 chloro-p-phenylenediamine, dianisidine, methyl p 25 aminobenzoate, ethyl p-aminobenzoate, n-propyl p aminobenzoate, isopropyl p-aminobenzoate, butyl p aminobenzoate, dodecyl p-aminobenzoate, benzyl p aminobenzoate, o-aminobenzophenone, m-aminoaceto- 131 phenone, p-aminoacetophenone, m-aminobenzamide, o aminobenzamide, p-aminobenzamide, p-amino-N-methyl benzamide, 3 -amino-4-methylbenzamide, 3-amino-4 methoxybenzamide, 3 -amino-4-chlorobenzamide, p-(N 5 phenylcarbamoyl)aniline, p-[N-(4-chlorophenyl) carbamoyl]aniline, p-[N-(4-aminophenyl)carbamoyl] aniline, 2-methoxy-5-(N-phenylcarbamoyl)aniline, 2 methoxy-5-[N-(2'-methyl-3'-chlorophenyl)carbamoyl] aniline, 2-methoxy-5-[N-(2'-chlorophenyl)carbamoyl] 10 aniline, 5-acetylamino-2-methoxyaniline, 4-acetyl aminoaniline, 4-(N-methyl-N-acetylamino)aniline, 2,5 diethoxy-4-(N-benzoylamino)aniline, 2,5-dimethoxy-4-(N benzoylamino)aniline, 2-methoxy-4-(N-benzoylamino)-5 methylaniline, 4 -sulfamoylaniline, 3 -sulfamoylaniline, 15 2-(N-ethyl-N-phenylaminosulfonyl)aniline, 4-dimethyl aminosulfonylaniline, 4 -diethylaminosulfonylaniline, sulfathiazole, 4-aminodiphenyl sulfone, 2-chloro-5-N phenylsulfamoylaniline, 2-methoxy-5-N,N-diethyl sulfamoylaniline, 2,5-dimethoxy-4-N-phenysulfamoyl 20 aniline, 2 -methoxy-5-benzylsulfonylaniline, 2 phenoxysulfonylaniline, 2-(2'-chlorophenoxy)sulfonyl aniline, 3 -anilinosulfonyl-4-methylaniline, bis[4-(m aminophenoxy)phenyl] sulfone, bis[4-(p-aminophenoxy) phenyll sulfone, bis[3-methyl-4-(p-aminophenoxy)phenyl] 25 sulfone, 3
,
3 '-dimethoxy-4,4'-diaminobiphenyl, 3,3' dimethyl-4,4'-diaminobiphenyl, 2,2'-dichloro-4,4' diamino-5,5'-dimethoxybiphenyl, 2,2' ,,5'-tetrachloro 4 ,4'-diaminobiphenyl, o-tolidine sulfone, 2,4'- 132 diaminobiphenyl, 2,2'-diaminobiphenyl, 4,4'-diamino biphenyl, 2
,
2 '-dichloro-4,4'-diaminobiphenyl, 3,3' dichloro-4,4'-diaminobiphenyl, 2,2'-dimethyl-4,4' diaminobiphenyl, 4,4'-thiodianiline, 2,2'-dithio 5 dianiline, 4,4'-dithiodianiline, 4,4'-diaminodiphenyl ether, 3,3'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenylmethane, 3,4'-diamino diphenylmethane, bis(3-amino-4-chlorophenyl) sulfone, bis(3,4-diaminophenyl) sulfone, 4,4'-diaminodiphenyl 10 sulfone, 3,3'-diaminodiphenyl sulfone, 3,4'-diamino diphenyl sulfone, 3,3'-diaminodiphenylmethane, 4,4 diaminodiphenylamine, 4,4'-ethylenedianiline, 4,4' diamino-2,2'-dimethyldibenzyl, 3,3'-diaminobenzo phenone, 4 ,4'-diaminobenzophenone, 1,4-bis(4 15 aminophenoxy)benzene, 1,3-bis(4-aminophenoxy)benzene, 1,3-bis( 3 -aminophenoxy)benzene, 9,9-bis(4-aminophenyl) fluorene, 2,2-bis(4-aminophenoxyphenyl)propane, 4,4' bis(4-aminophenoxy)diphenyl, 3,3',4,4'-tetraamino diphenyl ether, 3,3',4,4'-tetraaminodiphenyl sulfone, 20 3,3', 4
,
4 '-tetraaminobenzophenone, 3-aminobenzonitrile, 4-phenoxyaniline, 3-phenoxyaniline, 4,4'-methylenebis o-toluidine, 4,4'-(p-phenyleneisopropylidene)-bis-(2,6 xylidine), o-chloro-p-nitroaniline, o-nitro-p chloroaniline, 2,6-dichloro-4-nitroaniline, 5-chloro-2 25 nitroaniline, 2-amino-4-chlorophenol, o-nitroaniline, m-nitroaniline, p-nitroaniline, 2-methyl-4-nitro aniline, m-nitro-p-toluidine, 2-amino-5-nitrobenzo nitrile, Metol, 2,4-diaminophenol, N-(-hydroxyethyl)- 133 o-aminophenol sulfate, sulfanilic acid, metanilic acid, 4B acid, C acid, 2B acid, p-fluoroaniline, o-fluoro aniline, 3-chloro-4-fluoroaniline, 2,4-difluoroaniline, 2,3,4-trifluoroaniline, m-aminobenzotrifluoride, m 5 toluylenediamine, 2-aminothiophenol, 2-amino-3-bromo-5 nitrobenzonitrile, diphenylamine, p-aminodiphenylamine, octylated diphenylamine, 2-methyl-4-methoxydiphenyl amine, N,N-diphenyl-p-phenylenediamine, dianisidine, 3,3'-dichlorobenzidine, 4,4'-diaminostilbene-2,2' 10 disulfonic acid, benzylethylaniline, 1,8-naphthalene diamine, sodium naphthionate, Tobias acid, H acid, J acid, phenyl J acid, 1,4-diaminoanthraquinone, 1,4 diamino-2,3-dichloroanthraquinone, etc.; heterocyclic compound amines such as 3-amino-1,2,4-triazole, 2 15 aminopyridine, 3-aminopyridine, 4-aminopyridine, ca amino-s-caprolactam, acetoguanamine, 2,4-diamino-6-[2' methylimidazolyl-(1)]ethyl-S-triazine, 2,3-diamino pyridine, 2,5-diaminopyridine, 2,3,5-triaminopyridine, 1-amino-4-methylpiperazine, 1-(2-aminoethyl)piperazine, 20 bis(aminopropyl)piperazine, N-(3-aminopropyl) morpholine, etc.; and aliphatic amines such as methylamine, ethylamine, dimethylamine, diethylamine, stearylamine, allylamine, diallylamine, isopropylamine, diisopropylamine, 2-ethylhexylamine, ethanolamine, 3 25 (2-ethylhexyloxy)propylamine, 3-ethoxypropylamine, diisobutylamine, 3-(diethylamino)propylamine, di-2 ethylhexylamine, 3-(dibutylamino)propylamine, t butylamine, propylamine, 3-(methylamino)propylamine, 3- 134 (dimethylamino) propylamine, 3-methoxypropylamine, methylhydrazine, 1-methylbutylamine, methanediamine, 1,4-diaminobutane, cyclohexanemethylamine, cyclohexyl amine, 4 -methylcyclohexylamine, 2-bromoethylamine, 2 5 methoxyethylamine, 2-ethoxymethylamine, 2-amino-1 propanol, 2-aminobutanol, 3-amino-1,2-propanediol, 1,3 diamino-2-hydroxypropane, 2-aminoethanethiol, ethylene diamine, diethylenetriamine, hexamethylenediamine, etc. Of the above-exemplified amine compounds, 10 aniline derivatives having at least one amino group and represented by the following formula (VIII) are especially preferable:
R
1
X
1 X2 R3 1 1 R (VIII) R2 R4 wherein R 1 , R 2 , R 3 and R 4 are independently a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group 15 or an amino group, X, and X 2 are independently an amino group or a group represented by the formula (b): --- O a NH2 (b) and Yi is any of -SO 2 -, -0-, - (S) n-, - (CH 2 )n-, -CO-, -CONH- and a group represented by any of the formulas (a): 135 & O CH --- O __ _ 0 CH 3
CH
3 CH 3 -- C c - -- Q --- (a) L . I
CH
3 CH 3 -0 0 or is absent, and n is 1 or 2. As the OH group-containing compound that is reacted with the isocyanate to form one or more urethane groups, any compound may be used so long as it 5 contains one or more OH groups. The OH group containing compound includes, for example, phenols such as phenol, cresol, xylenol, p-ethylphenol, o-isopropyl- 136 phenol, resorcinol, p-tert-butylphenol, p-tert octylphenol, 2-cyclohexylphenol, 2-allylphenol, 4 indanol, thymol, 2-naphthol, p-nitrophenol, o-chloro phenol, p-chlorophenol, 2,2-bis(4-hydroxyphenyl) 5 propane, 2,2-bis(hydroxyphenyl)butane, 2,2-bis(hydroxy phenyl)pentane, 2,2-bis(hydroxyphenyl)heptane, catechol, 3-methylcatechol, 3-methoxycatechol, pyrogallol, hydroquinone, methylhydroquinone, 4 phenylphenol, p,p'-biphenol, 4-cumylphenol, butyl 10 bis(4-hydroxyphenyl)acetate, benzyl bis(4-hydroxy phenyl)acetate, bis(4-hydroxyphenyl) sulfone, bis(3 methyl-4-hydroxyphenyl) sulfone, bis(3,5-dimethyl-4 hydroxyphenyl) sulfone, 4-hydroxyphenyl-4'-methylphenyl sulfone, 3-chloro-4-hydroxyphenyl-4'-methylphenyl 15 sulfone, 3,4-dihydroxyphenyl-4'-methylphenyl sulfone, 4-isopropyloxyphenyl-4'-hydroxyphenyl sulfone, bis(2 allyl-4-hydroxyphenyl) sulfone, 4-hydroxyphenyl-4' benzyloxyphenyl sulfone, 4-isopropylphenyl-4' hydroxyphenyl sulfone, 4-hydroxy-4'-isopropoxydiphenyl 20 sulfone, bis(2-methyl-3-tert-butyl-4-hydroxyphenyl) sulfide, 4,4'-dihydroxydiphenyl ether, 4,4' thiodiphenol, 4,4'-dihydroxybenzophenone, 2,2-bis(4 hydroxyphenyl)hexafluoropropane, 4,4'-dihydroxy diphenylmethane, 3,3'-dihydroxydiphenylamine, bis(4 25 hydroxy-3-methylphenyl) sulfide, bis(4-(2-hydroxy) phenyl) sulfone, 2,4-dihydroxybenzophenone, 2,2',4,4' tetrahydroxybenzophenone, phenyl salicylate, salicylanilide, methyl 4-hydroxybenzoate, benzyl 4- 137 hydroxybenzoate, (4'-chlorobenzyl) 4-hydroxybenzoate, ethyl 1,2-bis(4'-hydroxybenzoate), pentyl 1,5-bis(4' hydroxybenzoate), hexyl 1,6-bis(4'-hydroxybenzoate), dimethyl 3-hydroxyphthalate, stearyl gallate, lauryl 5 gallate, methyl gallate, 4-methoxyphenol, 4 (benzyloxy)phenol, 4-hydroxybenzaldehyde, 4-n octyloxysalicylic acid, 4-n-butyloxysalicylic acid, 4 n-pentyloxysalicylic acid, 3-n-dodecyloxysalicylic acid, 3-n-octanoyloxysalicylic acid, 4-n-octyloxy 10 carbonylaminosalicylic acid, 4-n-octanoyloxy carbonylaminosalicylic acid, etc. However, as such phenols, those having an amino group are not desirable. Since the amino group has a higher reactivity towards an isocyanate group than does an OH group, the amino 15 group reacts with the isocyanate group before the OH group, so that it is difficult in some cases to obtain the desired compound. The OH group-containing compound also includes alcohols such as methanol, ethanol, propanol, butanol, pentanol, hexanol, heptanol, 20 octanol, isopropanol, iosbutanol, isoheptanol, 2-ethyl 1-hexanol, 1-decanol, 2-pentanol, 3-hexanol, tert butanol, tert-amyl alcohol, methyl Cellosolve, butyl Cellosolve, methyl Carbitol, allyl alcohol, 2-methyl-2 propen-l-ol, benzyl alcohol, 4-pyridinemethanol, phenyl 25 Cellosolve, furfuryl alcohol, cyclohexanol, cyclohexyl methanol, cyclopentanol, 2-chloroethanol, 1-chloro-3 hydroxypropane, glycerin, glycerol, etc.; polyether type polyols such as polypropylene glycols, polytetra- 138 methylene ether glycols, adipate-derived polyols, epoxy-modified polyols, polyether ester polyols, polycarbonate polyols, polycaprolactone diols, phenolic polyols, amine-modified polyols, etc.; and polyols such 5 as ethylene glycol, diethylene glycol, 1,3-propanediol, 1, 2-propanediol, propylene glycol, dipropylene glycol, 1,4-butanediol, 1,5-pentanediol, 1, 6-hexanediol, 1,6 hexane glycol, 1,9-nonanediol, acryl polyols, fluoro carbon polyols, polybutadiene polyols, polyhydroxy 10 polyols, trimethylolpropane, trimethylolethane, hexanetriol, phosphoric acid, neopentyl glycol, pentaerythritol, castor-oil-derived polyols, polymer polyols, methylpentanediol, halogen-containing polyols, phosphorus-containing polyols, ethylenediamine, a 15 methylglucoside, sorbitol, sucrose, etc. As the urea-urethane compound used as developer in each of the twenty-first and twenty-second aspects of the present invention, urea-urethane compounds represented by any of the following general 20 formulas (I) to (VII) are also preferable: 0 0 || ||
X-O-C-N-Y
0 -N-C-N-Z (I) H H H wherein X and Z are independently an aromatic compound residue, a heterocyclic compound residue or an aliphatic compound residue, each of the residues may have one or more substituents, and YO is a group 25 selected from the group consisting of tolylene group, 139 xylylene group, naphthylene group, hexamethylene group and -#-CH 2 -4- group wherein -#- is a phenylene group; 0 0 0 X-0-C-N-Y-N-C-N-Y-N--C- X ("I) H H H H wherein X and Y are independently an aromatic compound residue, a heterocyclic compound residue or an 5 aliphatic compound residue, and each of the residues may have one or more substituents; 0 0 X-0-C-N-Y-N-C-Na (III) H H H n wherein X and Y are independently an aromatic compound residue, a heterocyclic compound residue or an aliphatic compound residue, a is a residue having a 10 valence of 2 or more, n is an integer of 2 or more, and each of the residues may have one or more substituents; o 0 Z-N-C-N-Y-N-C- (IV) H H H n wherein Z and Y are independently an aromatic compound residue, a heterocyclic compound residue or an aliphatic compound residue, P is a residue having a 15 valence of 2 or more, n is an integer of 2 or more, and each of the residues may have one or more substituents; NH - (V) 140 wherein hydrogen atom(s) of each benzene ring may be replaced by a substituent which is preferably an aromatic compound residue, an aliphatic compound residue or a heterocyclic compound residue though the 5 substituent may be a nitro group, a hydroxyl group, a carboxyl group, a nitroso group, a nitrile group, a carbamoyl group, a ureido group, an isocyanate group, a mercapto group, a sulfo group, a sulfamoyl group or a halogen atom, each of the residues may have one or more 10 substituents, y is a group selected from the group consisting of -SO 2 -, -0-, -(S)n-, -(CH 2 )n-, -CO-, -CONH and any of groups represented by the formulas (a); 141 OCHO -CH0
CH
3 CHH3 CH3 CH3 -C- --- -- ) O-- (a) I ' ' :I CH 3
CH
3 0 -- OQO0 --
-OO
0 or is absent, and n is 1 or 2; (VI) wherein hydrogen atom(s) of each benzene ring may be replaced by a substituent which is preferably an aromatic compound residue, an aliphatic compound 142 residue or a heterocyclic compound residue though the substituent may be a hydroxyl group, a nitro group, a nitrile group, a carbamoyl group, a sulfamoyl group, a carboxyl group, a nitroso group, an amino group, an 5 oxyamino group, a nitroamino group, a hydrazino group, a ureido group, an isocyanate group, a mercapto group, a sulfo group or a halogen atom, each of the residues may have one or more substituents, 6 is a group selected from the group consisting of -SO 2 -, -0-, 10 -(S) a-, -(CH 2 )n-, -CO-, -CONH-, -NH-, -CH(COOR 1 )-,
-C(CF
3
)
2 - and -CR 2
R
3 - or is absent, each of R 1 , R 2 and R 3 is an alkyl group, and n is 1 or 2; and 0 0 11 H H 11 H X--O-C-N-Y-N-C-N-Z (VII) wherein X, Y and Z are independently an aromatic compound residue, a heterocyclic compound residue or an 15 aliphatic compound residue, each of the residues may have one or more substituents, and each of X, Y and Z is preferably an aromatic compound residue or a hetero cyclic compound residue. The urea-urethane compounds of the formulas 20 (I) to (VII) are also quite novel. These novel compounds are useful in the case of recording materials which use a recording energy such as heat, pressure or the like. A process for producing the urea-urethane 143 compound of the formula (I) used in each of the twenty first and twenty-second aspects of the present inven tion is not limited. This compound can be obtained, for example, by reacting an OH group-containing 5 compound of the following general formula (IX) with an isocyanate compound of the following general formula (X) and an amine compound of the following general formula (XI) according to, for instance, the reaction formula (A) shown below: X-OH (IX) OCN-YO-NCO (X)
Z-NH
2 (XI) 10 wherein X and Z are independently an aromatic compound residue, a heterocyclic compound residue or an aliphatic compound residue, each of the residues may have one or more substituents, and Yo is a group selected from the group consisting of tolylene group, 15 xylylene group, naphthylene group, hexamethylene group and -4-CH 2 -#- group wherein -0- is a phenylene group. The term "aliphatic" used herein includes the term "alicyclic". 0 X-OH + OCN-Y 0 -NCO -CX-0- -- N-Y-NCO H 00 0 (A) X-0-C--N-YO-NCO + Z-NH 2 +* X-0-C-N-YO-N-C-N-Z H H H H 144 A process for producing the urea-urethane compound of the formula (II) used in each of the twenty-first and twenty-second aspects of the present invention is not limited. This compound can be 5 obtained, for example, by reacting an OH group containing compound of the general formula (IX) with an isocyanate compound of the following general formula (XII) and water according to, for instance, the reaction formula (B) shown below: OCN-Y-NCO (XII) 10 wherein Y is an aromatic compound residue, a heterocyclic compound residue or an aliphatic compound residue, and each of the residues may have one or more substituents. 0 X-OH +0CN-Y-NCO -- X-0- 6 - -Y-NCO (B) 2 (X-0-0--Y-NCO) + H 2 0-+ X-0-0-gY-N--rY-N-0-0-X A process for producing the urea-urethane 15 compound of the formula (III) used in each of the twenty-first and twenty-second aspects of the present invention is not limited. This compound can be obtained, for example, by reacting an OH group containing compound of the general formula (IX) with an 20 isocyanate compound of the general formula (XII) and an amine compound of the following general formula (XIII) according to, for instance, the reaction formula (C) or (D) shown below: 145 iNH2 )n(XIII) wherein a is a residue having a valence of 2 or more, and n is an integer of 2 or more. 0 X-OH +OCN-Y-NCO - X-0-6-N-Y-NCO (C) 00 0 n (X-0-6-N-Y-NCO) + a NH2 n +X-0---Y-N--i a 0n a(- NH 2 ) + n (OCN-Y-NCO) - a N-6-N-Y-NCO nH Hn a N-6-N-Y-NCO + n( X-OH (D) H H C)n IN X-0-0-r---r a A process for producing the urea-urethane compound of the formula (IV) used in each of the 5 twenty-first and twenty-second aspects of the present invention is not limited. This compound can be obtained, for example, by reacting an amine compound of the general formula (XI) with an isocyanate compound of the general formula (XII) and an OH group-containing 10 compound of the following general formula (XIV) according to, for instance, the reaction formula (E) or (F) shown below: P(OH) (XIV) 146 wherein 0 is a residue having a valence of 2 or more, and n is an integer of 2 or more. 0
Z-NH
2 + OCN-Y-NCO x Z-N---N-Y-NCO H H (E) 00 0 n Z-N-0-N-Y-NC + (OH ) + Z-N-0-N-Y-N-0-0 p (H H n)( H H H + n 0 0(OH) + n(OCN-Y-NCO) +P 0-6-N-Y-NCO H n 0 P 0-0-N-Y-NCO n Z-NH 2 (F) Hn+ Z-N-9-N-Y-N-0- P H H H 0 The compounds of the general formulas (IX) to (XIV) are explained below in further detail which can 5 be used for synthesis of the urea-urethane compounds of the above formulas (I) to (IV). The OH group-containing compound of the general formula (IX) is not particularly limited so long as it has one or more OH groups. This compound 10 includes, for example, monophenols such as phenol, cresol, xylenol, p-ethylphenol, o-isopropylphenol, resorcinol, p-tert-butylphenol, p-tert-octylphenol, 2 cyclohexylphenol, 2-allylphenol, 4-indanol, thymol, 2 naphthol, p-nitrophenol, o-chlorophenol, p-chloro 15 phenol, 4-phenylphenol, 4-hydroxyphenyl-4'-methylphenyl sulfone, 3-chloro-4-hydroxyphenyl-4'-methylphenyl 147 sulfone, 4 -isopropylphenyl-4'-hydroxyphenyl sulfone, 4 isopropyloxyphenyl-4'-hydroxyphenyl sulfone, 4 hydroxyphenyl-4'-benzyloxyphenyl sulfone, 4-isopropyl phenyl-4'-hydroxyphenyl sulfone, 4-hydroxy-4' 5 isopropoxydiphenyl sulfone, phenyl salicylate, salicylanilide, methyl 4-hydroxybenzoate, benzyl 4 hydroxybenzoate, (4'-chlorobenzyl) 4-hydroxybenzoate, ethyl 1,2-bis(4'-hydroxybenzoate), pentyl 1,5-bis(4' hydroxybenzoate), hexyl 1,6-bis(4'-hydroxybenzoate), 10 dimethyl 3-hydroxyphthalate, 4-methoxyphenol, 4 (benzyloxy)phenol, 4-hydroxybenzaldehyde, 4-n-octyloxy salcylic acid, 4 -n-butyloxysalcylic acid, 4-n pentyloxysalcylic acid, 3 -n-dodecyloxysalcylic acid, 3 n-octanoyloxysalcylic acid, 4 -n-octyloxycarbonyl 15 aminosalcylic acid, 4 -n-octanoyloxycarbonylamino salcylic acid, etc. The compound of the general formula (IX) also includes diphenols such as 2,2-bis(4 hydroxyphenyl)propane, 2,2-bis(hydroxyphenyl)butane, 2,2-bis(hydroxyphenyl)pentane, 2,2-bis(hydroxyphenyl) 20 heptane, catechol, 3-methylcatechol, 3-methoxycatechol, pyrogallol, hydroquinone, methylhydroquinone, 4 phenylphenol, 4,4'-biphenol, 4-cumylphenol, butyl bis(4-hydroxyphenyl)acetate, benzyl bis(4-hydroxy phenyl)acetate, bis(4-hydroxyphenyl) sulfone, bis(3 25 methyl-4-hydroxyphenyl) sulfone, bis(3,5-dimethyl-4 hydroxyphenyl) sulfone, 3,4-dihydroxyphenyl-4' methylphenyl sulfone, bis(2-allyl-4-hydroxyphenyl) sulfone, bis( 2 -methyl-3-tert-butyl-4-hydroxyphenyl) 148 sulfide, 4,4'-dihydroxydiphenyl ether, 4,4' thiodiphenol, 4,4'-dihydroxybenzophenone, 2,2-bis(4 hydroxyphenyl)hexafluoropropane, 4,4'-dihydroxy diphenylmethane, 3,3' -dihydroxydiphenylamine, bis(4 5 hydroxy-3-methylphenyl) sulfide, etc. However, as such OH group-containing compounds, those having an amino group are not desirable. When the amino group is present together with the OH group(s), the amino group has a higher reactivity towards an isocyanate group 10 than does the OH group and hence reacts with the isocyanate group before the OH group, so that it is difficult in some cases to obtain the desired compound. The compound of the general formula (IX) further includes monohydric alcohols such as methanol, ethanol, 15 propanol, butanol, pentanol, hexanol, heptanol, octanol, isopropanol, isobutanol, isopentanol, 2-ethyl 1-hexanol, 1-decanol, 2-pentanol, 3-hexanol, tert butanol, tert-amyl alcohol, methyl Cellosolve, butyl Cellosolve, methyl Carbitol, allyl alcohol, 2-methyl-2 20 propen-l-ol, benzyl alcohol, 4-pyridinemethanol, phenyl Cellosolve, furfuryl alcohol, cyclohexanol, cyclohexyl methanol, cyclopentanol, 2-chloroethanol, 1-chloro-3 hydroxypropane, glycerin, glycerol, etc. As the compound of the general formula (IX), there may also be 25 used polyether type polyols such as polypropylene glycols, polytetramethylene ether glycols, adipate derived polyols, epoxy-modified polyols, polyether ester polyols, polycarbonate polyols, polycaprolactone 149 diols, phenolic polyols, amine-modified polyols, etc.; and polyols such as ethylene glycol, diethylene glycol, 1,3-propanediol, 1,2-propanediol, propylene glycol, dipropylene glycol, 1,4-butanediol, 1,5-pentanediol, 5 1,6-hexanediol, 1,6-hexane glycol, 1,9-nonanediol, acryl polyols, fluorocarbon polyols, polybutadiene polyols, polyhydroxy polyols, trimethylolpropane, trimethylolethane, hexanetriol, phosphoric acid, neopentyl glycol, pentaerythritol, castor-oil-derived 10 polyols, polymer polyols, methylpentanediol, halogen containing polyols, phosphorus-containing polyols, ethylenediamine, cx-methylglucoside, sorbitol, sucrose, etc. Of these, the monophenols are preferably used. The isocyanate compound of the general 15 formula (X) includes 2,4-toluene diisocyanate, 2,6 toluene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, 1,5-naphthylene diisocyanate, m-xylylene diisocyanate, etc. Of these, the toluene diisocyanates are preferable. 20 The isocyanate compound of the general formula (XII) is not particularly limited so long as it has two or more isocyanate groups. This compound includes, for example, p-phenylene diisocyanate, 2,5 dimethoxybenzene-1,4-diisocyanate, 2,4-toluene 25 diisocyanate, 2,6-toluene diisocyanate, diphenylmethane diisocyanate, o-tolidine diisocyanate, 1,5-naphthylene diisocyanate, dianisidine diisocyanate, 9-ethyl carbazole-3,6-diisocyanate, 3,3'-dimethyl-4,4'- 150 diphenylmethane dilsocyanate, hexamethylene diiso cyanate, isophorone diisocyanate, triphenylmethane triisocyanate, tris(4-phenylisocyanato)thiophosphate, 4,4',4"-triisocyanato-2,5-dimethoxytriphenylamine, 5 4,4',4"-triisocyanatotriphenylamine, m-xylylene diisocyanate, lysine diisocyanate, dimer acid diiso cyanate, isopropylidene bis-4-cyclohexylisocyanate, dicyclohexylmethane diisocyanate and methylcyclohexane diisocyanate. As the isocyanate compound of the 10 general formula (XII), there may also be used diisocyanate dimers such as N,N'-(4,4'-dimethyl-3,3' diphenyldiisocyanato)urethodione (Desmodule TT, a trade name), a toluene diisocyanate dimer; and diisocyanate trimers such as 4,4',4"-trimethyl-3,3',3"-triiso 15 cyanato-2,4,6-triphenylcyanurate. There may also be used water adduct isocyanates of toluene diisocyanate, diphenylmethane diisocyanate and the like, such as 1,3 bis(3-isocyanato-4-methylphenyl)urea; polyol adducts such as trimethylolpropane adduct of toluene 20 diisocyanate (Desmodule L, a trade name); and amine adducts. There may also be used compounds having two or more isocyanate groups, among the isocyanate compounds and isocyanate adduct compounds described in 25 the specifications of JP-A-10-76757 and JP-A-10-95171. An especially preferable example of the isocyanate compound of the general formula (XII) is toluene diisocyanate.
151 The amine compound of the general formula (XI) is not particularly limited so long as it has one or more amino groups. This compound includes, for example, aromatic monoamines such as aniline, o 5 toluidine, m-toluidine, p-toluidine, o-anisidine, p anisidine, p-phenetidine, 2,4-dimethoxyaniline, 2,5 dimethoxyaniline, 3,4-dimethoxyaniline, p-amino acetanilide, p-aminobenzoic acid, o-aminophenol, m aminophenol, p-aminophenol, 2,3-xylidine, 2,4-xylidine, 10 3,4-xylidine, 2,6-xylidine, 4-aminobenzonitrile, anthranilic acid, p-cresidine, 2,5-dichloroaniline, 2,6-dichloroaniline, 3,4-dichloroaniline, 3,5 dichloroaniline, 2,4,5-trichloroaniline, a-naphthyl amine, aminoanthracene, o-ethylaniline, o-chloro 15 aniline, m-chloroaniline, p-chloroaniline, methyl p aminobenzoate, ethyl p-aminobenzoate, n-propyl p aminobenzoate, isopropyl p-aminobenzoate, butyl p aminobenzoate, dodecyl p-aminobenzoate, benzyl p aminobenzoate, o-aminobenzophenone, m-aminoaceto 20 phenone, p-aminoacetophenone, m-aminobenzamide, o aminobenzamide, p-aminobenzamide, p-amino-N methylbenzamide, 3-amino-4-methylbenzamide, 3-amino-4 methoxybenzamide, 3-amino-4-chlorobenzamide, p-(N phenylcarbamoyl)aniline, p-[N-(4-chlorophenyl) 25 carbamoyl]aniline, p-[N-(4-aminophenyl)carbamoyl] aniline, 2-methoxy-5-(N-phenylcarbamoyl)aniline, 2 methoxy-5-[N-(2'-methyl-3'-chlorophenyl)carbamoyl] aniline, 2-methoxy-5-[N-(2'-chlorophenyl)carbamoyl]- 152 aniline, 5-acetylamino-2-methoxyaniline, 4-acetyl aminoaniline, 2-methoxy-4-(N-benzoylamino)-5 methylaniline, 4-sulfamoylaniline, 3-sulfamoylaniline, 2- (N-ethyl-N-phenylaminosulfonyl) aniline, 4-dimethyl 5 aminosulfonylaniline, 4-diethylaminosulfonylaniline, sulfathiazole, 4-aminodiphenyl sulfone, 2-chloro-5-N phenylsulfamoylaniline, 2-methoxy-5-N,N-diethyl sulfamoylaniline, 2,5-dimethoxy-4-N-phenysulfamoyl aniline, 2-methoxy-5-benzylsulfonylaniline, 2 10 phenoxysulfonylaniline, 2-(2'-chlorophenoxy)sulfonyl aniline, 3-anilinosulfonyl-4-methylaniline, o-chloro-p nitroaniline, o-nitro-p-chloroaniline, 2, 6-dichloro-4 nitroaniline, 5-chloro-2-nitroaniline, 2-amino-4 chiorophenol, o-nitroaniline, m-nitroaniline, p 15 nitroaniline, 2-methyl-4-nitroaniline, m-nitro-p toluidine, 2-amino-5-nitrobenzonitrile, sulfanilic acid, metanilic acid, 4B acid, C acid, 2B acid, p fluoroaniline, o-fluoroaniline, 3-chloro-4-fluoro aniline, 2,4-difluoroaniline, 2,3,4-trifluoroaniline, 20 m-aminobenzotrifluoride, 2-amino-3-bromo-5-nitrobenzo nitrile, etc.; and aromatic diamines such as 4,4' diamino-3,3'-diethyldiphenylmethane, 4,4'-diamino benzanilide, 3, 5-diaminochlorobenzene, diaminodiphenyl ether, 3,3'-dichloro-4,4'-diaminodiphenylmethane, 3,3' 25 dimethyl-4,4'-diaminodiphenylmethane, tolidine base, dianisidine, bis[4-(m-aminophenoxy)phenyl] sulfone, bis[4-(p-aminophenoxy)phenyl] sulfone, bis[3-methyl-4 (p-aminophenoxy) phenyll sulfone, 3,3' -dimethoxy-4, 4'- 153 diaminobiphenyl, 3,3'-dimethyl-4,4'-diaminobiphenyl, 2,2'-dichloro-4,4'-diamino-5,5'-dimethoxybiphenyl, 2,2',5, 5 '-tetrachloro-4,4'-diaminobiphenyl, o-tolidine sulfone, 2,4'-diaminobiphenyl, 2,2'-diaminobiphenyl, 5 4,4'-diaminobiphenyl, 2,2'-dichloro-4,4'-diamino biphenyl, 3
,
3 '-dichloro-4,4'-diaminobiphenyl, 2,2' dimethyl-4,4'-diaminobiphenyl, 4,4'-thiodianiline, 2,2'-dithiodianiline, 4,4'-dithiodianiline, 4,4' diaminodiphenyl ether, 3,3'-diaminodiphenyl ether, 10 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl methane, 3,4'-diaminodiphenylmethane, bis(3-amino-4 chlorophenyl) sulfone, bis(3,4-diaminophenyl) sulfone, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfone, 3,3'-diamino 15 diphenylmethane, 4,4'-diaminodiphenylamine, 4,4' ethylenedianiline, 4,4'-diamino-2,2'-dimethyldibenzyl, 3,3'-diaminobenzophenone, 4,4'-diaminobenzophenone, 1,4-bis(4-aminophenoxy)benzene, 1,3-bis(4-amino phenoxy)benzene, 1,3-bis(3-aminophenoxy)benzene, 9,9 20 bis(4-aminophenyl)fluorene, 2,2-bis(4-aminophenoxy phenyl)propane, 4,4'-bis(4-aminophenoxy)diphenyl, dianisidine, 3,3'-dichlorobenzidine, etc. The amine compound of the general formula (XI) also includes, for example, heterocyclic compound amines such as 3-amino 25 1,2,4-triazole, 2-aminopyridine, 3-aminopyridine, 4 aminopyridine, a-amino-s-caprolactam, acetoguanamine, 2,4-diamino-6-[2'-methylimidazolyl-(l)lethyl-S triazine, 2,3-diaminopyridine, 2,5-diaminopyridine, 154 2,3,5-triaminopyridine, 1-amino-4-methylpiperazine, 1
(
2 -aminoethyl)piperazine, bis(aminopropyl)piperazine, N-(3-aminopropyl)morpholine, etc.; and aliphatic amines such as methylamine, ethylamine, stearylamine, 5 allylamine, isopropylamine, 2-ethylhexylamine, ethanolamine, 3-( 2 -ethylhexyloxy)propylamine, 3 ethoxypropylamine, 3-(diethylamino)propylamine, 3 (dibutylamino)propylamine, t-butylamine, propylamine, 3-(methylamino)propylamine, 3-(dimethylamino)propyl 10 amine, 3 -methoxypropylamine, methylhydrazine, 1 methylbutylamine, methanediamine, 1,4-diaminobutane, cyclohexanemethylamine, cyclohexylamine, 4-methyl cyclohexylamine, 2-bromoethylamine, 2-methoxy ethylamine, 2-ethoxymethylamine, 2-amino-1-propanol, 2 15 aminobutanol, 3 -amino-1,2-propanediol, 1,3-diamino-2 hydroxypropane, 2-aminoethanethiol, ethylenediamine, diethylenetriamine, hexamethylenediamine, etc. Of these, the aromatic monoamines are preferably used. The amine compound of the general formula 20 (XIII) is not particularly limited so long as it has two or more amino groups. This compound includes, for example, aromatic amines such as 4,4'-diamino-3,3' diethyldiphenylmethane, 4,4'-diaminobenzanilide, 3,5 diaminochlorobenzene, diaminodiphenyl ether, 3,3' 25 dichloro-4,4'-diaminodiphenylmethane, 3,3'-dimethyl 4,4'-diaminodiphenylmethane, tolidine base, dianisidine, bis[4-(m-aminophenoxy)phenyl] sulfone, bis[4-(p-aminophenoxy)phenyl] sulfone, bis[3-methyl-4- 155 (p-aminophenoxy)phenyl] sulfone, 3,3'-dimethoxy-4,4' diaminobiphenyl, 3,3'-dimethyl-4,4'-diaminobiphenyl, 2,2'-dichloro-4,4'-diamino-5,5'-dimethoxybiphenyl, 2,2',5,5'-tetrachloro-4,4'-diaminobiphenyl, o-tolidine 5 sulfone, 2,4'-diaminobiphenyl, 2,2'-diaminobiphenyl, 4,4'-diaminobiphenyl, 2,2'-dichloro-4,4'-diamino biphenyl, 3,3'-dichloro-4,4'-diaminobiphenyl, 2,2' dimethyl-4,4'-diaminobiphenyl, 4,4'-thiodianiline, 2,2'-dithiodianiline, 4,4'-dithiodianiline, 4,4' 10 diaminodiphenyl ether, 3,3'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl methane, 3,4'-diaminodiphenylmethane, bis(3-amino-4 chlorophenyl) sulfone, bis(3,4-diaminophenyl) sulfone, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl 15 sulfone, 3,4'-diaminodiphenyl sulfone, 3,3'-diamino diphenylmethane, 4,4'-diaminodiphenylamine, 4,4' ethylenedianiline, 4,4'-diamino-2,2'-dimethyldibenzyl, 3,3'-diaminobenzophenone, 4,4'-diaminobenzophenone, 1,4-bis(4-aminophenoxy)benzene, 1,3-bis(4-amino 20 phenoxy)benzene, 1,3-bis(3-aminophenoxy)benzene, 9,9 bis(4-aminophenyl)fluorene, 2,2-bis(4-aminophenoxy phenyl)propane, 4,4'-bis(4-aminophenoxy)diphenyl, dianisidine, 3,3'-dichlorobenzidine, tolidine base, o phenylenediamine, m-phenylenediamine, p-phenylene 25 diamine, etc. Of the above-exemplified amine compounds, aniline derivatives having at least two amino groups and represented by the following formula (VIII) are especially preferable: 156 R, X1 X 2 R3 (VIII) R2 R4 wherein R 1 , R 2 , R 3 and R 4 are independently a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or an amino group, X, and X 2 are independently an amino group or a group represented by the formula (b): --- O a NH2 (b) 5 and Yi is any of -SO 2 -, -0-, - (S) n-, - (CH 2 )-, -CO-, -CONH- and a group represented by any of the formulas (a) 157
CH
3 -0 0
O;H
3
CH
3
CH
3 CH3_ -c c- -O< O- (a)
CH
3
CH
3 0 00 or is absent, and n is 1 or 2. The OH group-containing compound of the general formula (XIV) is not particularly limited so long as it has two or more OH groups. This compound 5 includes, for example, diphenols such as 2,2-bis(4 hydroxyphenyl) propane, 2, 2-bis (hydroxyphenyl) butane, 158 2,2-bis(hydroxyphenyl)pentane, 2,2-bis(hydroxyphenyl) heptane, catechol, 3-methylcatechol, 3-methoxycatechol, pyrogallol, hydroquinone, methylhydroquinone, p,p' biphenol, butyl bis(4-hydroxyphenyl)acetate, benzyl 5 bis(4-hydroxyphenyl)acetate, bis(4-hydroxyphenyl) sulfone, bis(3-methyl-4-hydroxyphenyl) sulfone, bis( 3 ,5-dimethyl-4-hydroxyphenyl) sulfone, 3,4 dihydroxyphenyl-4'-methylphenyl sulfone, bis(2-allyl-4 hydroxyphenyl) sulfone, bis(2-methyl-3-tert-butyl-4 10 hydroxyphenyl) sulfide, 4,4'-dihydroxydiphenyl ether, 4,4'-thiodiphenol, 4,4'-dihydroxybenzophenone, 2,2 bis(4-hydroxyphenyl)hexafluoropropane, 4,4'-dihydroxy diphenylmethane, 3,3'-dihydroxydiphenylamine, bis(4 hydroxy-3-methylphenyl) sulfide, etc. However, as such 15 diphenols, those having an amino group are not desirable. Since the amino group has a higher reactivity towards an isocyanate group than does an OH group, the amino group reacts with the isocyanate group before the OH group, so that it is difficult in some 20 cases to obtain the desired compound. The OH group containing compound of the general formula (XIV) also includes polyether type polyols such as polypropylene glycols, polytetramethylene ether glycols, adipate derived polyols, epoxy-modified polyols, polyether 25 ester polyols, polycarbonate polyols, polycaprolactone diols, phenolic polyols, amine-modified polyols, etc.; and polyols such as ethylene glycol, diethylene glycol, 1,3-propanediol, 1,2-propanediol, propylene glycol, W 159 dipropylene glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,6-hexane glycol, 1,9-nonanediol, acryl polyols, fluorocarbon polyols, polybutadiene polyols, polyhydroxy polyols, trimethylolpropane, 5 trimethylolethane, hexanetriol, phosphoric acid, neopentyl glycol, pentaerythritol, castor-oil-derived polyols, polymer polyols, methylpentanediol, halogen containing polyols, phosphorus-containing polyols, ethylenediamine, a-methylglucoside, sorbitol, sucrose, 10 etc. A process for producing the urea-urethane compound of the formula (V) used in each of the twenty first and twenty-second aspects of the present inven tion is not limited. This compound can be obtained, 15 for example, by reacting a monophenol compound with an aromatic diisocyanate compound and a diamine compound of the following general formula (XV) according to, for instance, the reaction formula (G) or (H) shown below: H2N 7
NH
2 (XV) wherein hydrogen atom(s) of each benzene ring may be 20 replaced by a substituent which is preferably an aromatic compound residue, an aliphatic compound residue or a heterocyclic compound residue though the substituent may be a nitro group, a hydroxyl group, a carboxyl group, a nitroso group, a nitrile group, a 25 carbamoyl group, a ureido group, an isocyanate group, a 160 mercapto group, a sulfo group, a sulfamoyl group or a halogen atom, each of the residues may have one or more substituents, and y is any of -SO,-, -0-, -(S)n-, -(CH2)n-, -CO-, -CONH- and a group represented by any of 5 the formulas (a);
CH
3 -0-0-10 0
CH
3
CH
3 CH 3 -C -- - O- (a)
CH
3 CH 3 0 I I 00 or is absent, and n is 1 or 2.
161 -OH + OCN-- -NCO 0- --- NK -NCO (G) 2 -- O- -- N. NCO + H 2 N - y NH2 HH O- N0 NC H, Ho7 H OCN - + - 2 0 HH OCN- -N--N N- - N- -O H HKH H (H) K>K- _ K> 0 OH 0-NT N- --- y-N-u N N-8 -0'i1 HK kHK KTo H M ~ H A process for producing the urea-urethane compound of the formula (VI) used in each of the twenty-first and twenty-second aspects of the present invention is not limited. This compound can be 5 obtained, for example, by reacting an aniline deriva tive with an aromatic diisocyanate compound and a dihydroxy compound of the following general formula (XVI) according to, for instance, the reaction formula 162 (J) or (K) shown below: HO- SOH (XVI) wherein hydrogen atom(s) of each benzene ring may be replaced by a substituent which is preferably an aromatic compound residue, an aliphatic compound 5 residue or a heterocyclic compound residue though the substituent may be a hydroxyl group, a nitro group, a nitrile group, a carbamoyl group, a sulfamoyl group, a carboxyl group, a nitroso group, an amino group, an oxyamino group, a nitroamino group, a hydrazino group, 10 a ureido group, an isocyanate group, a mercapto group, a sulfo group or a halogen atom, each of the residues may have one or more substituents, 6 is any of -SO 2 -, -0-, -(S)n-, -(CH 2 )n-, -CO-, -CONH-, -NH-, -CH(COOR 1 )-, -C (CF 3 ) 2- and -CR 2
R
3 - or is absent, R 1 , R 2 and R 3 are 15 independently an alkyl group, and n is 1 or 2.
163 NH2+ OCN- -<NCO K N-C-N NCO H H (J) 2 -N-6-NK NCO + HO 1 OH H HHO- 1
-
K 0~C - -1N 0I H<0 0N- N N-0 N K~HAKH 6± -O--N± N 0KHH H1_ OCN_ -C- S O- -N NO + 2 C - N-0-O S f' O- -N N- O-N HQHK, , HH 8 H (K) The compounds usable for synthesizing the urea-urethane compound of the formula (V) or (VI) used in each of the twenty-first and twenty-second aspects of the present invention are explained below in detail. 5 The phenolic compound usable for synthesizing the urea-urethane compound of the formula (V) is not particularly limited so long as it has one or more OH groups on the benzene ring. In addition, hydrogen atom(s) of the benzene ring may be replaced by a 164 substituent other than OH group, i.e., an aromatic compound residue, an aliphatic compound residue, a heterocyclic compound residue, a nitro group, a carboxyl group, a nitroso group, a nitrile group, a 5 carbamoyl group, a ureido group, an isocyanate group, a mercapto group, a sulfo group, a sulfamoyl group or a halogen atom. Preferable examples of the phenolic compound are phenols such as phenol, cresol, xylenol, p 10 ethylphenol, o-isopropylphenol, resorcinol, p-tert butylphenol, p-tert-octylphenol, 2-cyclohexylphenol, 2 allylphenol, 4-indanol, thymol, 2-naphthol, nitro substituted phenols (e.g. p-nitrophenol), halogen substituted phenols (e.g. o-chlorophenol and p 15 chlorophenol), 4-phenylphenol, 4-hydroxyphenyl-4' methylphenyl sulfone, 3-chloro-4-hydroxyphenyl-4' methylphenyl sulfone, 4-isopropylphenyl-4'-hydroxy phenyl sulfone, 4-isopropyloxyphenyl-4'-hydroxyphenyl sulfone, 4-hydroxyphenyl-4'-benzyloxyphenyl sulfone, 4 20 isopropylphenyl-4'-hydroxyphenyl sulfone, 4-hydroxy-4' isopropoxydiphenyl sulfone, phenyl salicylate, salicylanilide, methyl 4-hydroxybenzoate, benzyl 4 hydroxybenzoate, (4'-chlorobenzyl) 4-hydroxybenzoate, dimethyl 3-hydroxyphthalate, 4-methoxyphenol, 4 25 (benzyloxy)phenol, 4-hydroxybenzaldehyde, 4-n-octyloxy salicylic acid, 4-n-butyloxysalicylic acid, 4-n pentyloxysalicylic acid, 3-n-dodecyloxysalicylic acid, 3 -n-octanoyloxysalicylic acid, 4-n-octyloxycarbonyl- 165 aminosalicylic acid, 4-n-octanoyloxycarbonyl aminosalicylic acid, etc. As the phenolic compound, there may also be used phenolic compounds having one or more substituents including carboxyl group, nitroso 5 group, nitrile group, carbamoyl group, ureido group, isocyanate group, mercapto group, sulfo group, sulfamoyl group, etc. However, as such phenols, those having an amino group are not desirable. Since the amino group has a higher reactivity towards an 10 isocyanate group than does an OH group, the amino group reacts with the isocyanate group before the OH group, so that it is difficult in some cases to obtain the desired compound. The aromatic diisocyanate compound usable for 15 synthesizing the urea-urethane compound of the formula (V) or (VI) is not particularly limited so long as it has two isocyanate groups bonded to its benzene ring. The aromatic diisocyanate compound includes, for example, p-phenylene diisocyanate, 2,5-dimethoxy 20 benzene-1,4-diisocyanate, 2,4-toluene diisocyanate and 2,6-toluene diisocyanate. Especially preferable examples of the aromatic diisocyanate compound are toluene diisocyanates. Of the toluene diisocyanates, 2,4-toluene diisocyanate is preferable. Besides 2,4 25 toluene diisocyanate, mixtures of 2.4-toluene diisocyanate and 2,6-toluene diisocyanate are generally on the market and available at a low price and may also be used as the aromatic diisocyanate. The mixtures of 166 these toluene diisocyanate isomers are liquid at ordinary temperatures. The diamine compound of the general formula (XV) which is usable for synthesizing the urea-urethane 5 compound of the formula (V) includes, for example, aromatic diamines such as 4,4'-diamino-3,3'-diethyl diphenylmethane, 4,4'-diaminobenzanilide, 3,5 diaminochlorobenzene, diaminodiphenyl ether, 3,3' dichloro-4,4'-diaminodiphenylmethane, 3,3'-dimethyl 10 4,4'-diaminodiphenylmethane, tolidine base, dianisidine, bis[4-(m-aminophenoxy)phenyl] sulfone, bis[4-(p-aminophenoxy)phenyl] sulfone, bis[3-methyl-4 (p-aminophenoxy)phenyl] sulfone, 3,3'-dimethoxy-4,4' diaminobiphenyl, 3,3'-dimethyl-4,4'-diaminobiphenyl, 15 2
,
2 '-dichloro-4,4'-diamino-5,5'-dimethoxybiphenyl, 2,2',5,5'-tetrachloro-4,4'-diaminobiphenyl, o-tolidine sulfone, 2,4'-diaminobiphenyl, 2,2'-diaminobiphenyl, 4,4'-diaminobiphenyl, 2,2'-dichloro-4,4'-diamino biphenyl, 3 ,3'-dichloro-4,4'-diaminobiphenyl, 2,2' 20 dimethyl-4,4'-diaminobiphenyl, 4,4'-thiodianiline, 2,2'-dithiodianiline, 4,4'-dithiodianiline, 4,4' diaminodiphenyl ether, 3,3'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl methane, 3 ,4'-diaminodiphenylmethane, bis(3-amino-4 25 chlorophenyl) sulfone, bis(3,4-diaminophenyl) sulfone, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfone, 3,3' diaminodiphenylmethane, 4,4'-diaminodiphenylamine, 167 4,4'-ethylenedianiline, 4,4'-diamino-2,2'-dimethyl dibenzyl, 3
,
31 -diaminobenzophenone, 4,4'-diaminobenzo phenone, 1,4-bis(4-aminophenoxy)benzene, 1,3-bis(4 aminophenoxy)benzene, 1,3-bis(3-aminophenoxy)benzene, 5 9,9-bis(4-aminophenyl)fluorene, 2,2-bis(4-aminophenoxy phenyl)propane, 4,4'-bis(4-aminophenoxy)diphenyl, dianisidine, 3,3'-dichlorobenzidine, etc. The aniline derivative usable for synthesiz ing the urea-urethane compound of the formula (VI) is 10 not particularly limited so long as it is an aniline compound having one or more amino groups on the benzene ring. In addition, hydrogen atom(s) of the benzene ring may be replaced by an aromatic compound residue, an aliphatic compound residue, a heterocyclic compound 15 residue, a hydroxyl group, a nitro group, a nitrile group, a carbamoyl group, a sulfamoyl group, a carboxyl group, a nitroso group, an amino group, an oxyamino group, a nitroamino group, a hydrazino group, a ureido group, an isocyanate group, a mercapto group, a sulfo 20 group or a halogen atom. Preferable examples of such an aniline compound are aniline, o-toluidine, m-toluidine, p toluidine, o-anisidine, p-anisidine, p-phenetidine, N,N-dimethyl-p- phenylenediamine, N,N-diethyl-p 25 phenylenediamine, 2,4-dimethoxyaniline, 2,5-dimethoxy aniline, 3,4-dimethoxyaniline, p-aminoacetanilide, carboxy-substituted anilines (e.g. p-aminobenzoic acid), hydroxyl-substituted anilines (e.g. o-amino- 168 phenol, m-aminophenol, 2-amino-4-chlorophenol and p aminophenol), 2,3-xylidine, 2,4-xylidine, 3,4-xylidine, 2,6-xylidine, nitrile-substituted anilines (e.g. 4 aminobenzonitrile), anthranilic acid, p-cresidine, 5 halogen-substituted anilines (e.g. 2,5-dichloroaniline, 2,6-dichloroaniline, 3,4-dichloroaniline, 3,5-dichloro aniline, 2, 4 ,5-trichloroaniline, o-chloroaniline, m chloroaniline and p-chloroaniline), a-naphthylamine, aminoanthracene, o-ethylaniline, methyl p-amino 10 benzoate, ethyl p-aminobenzoate, n-propyl p-amino benzoate, isopropyl p-aminobenzoate, butyl p-amino benzoate, dodecyl p-aminobenzoate, benzyl p-amino benzoate, o-aminobenzophenone, m-aminoacetophenone, p aminoacetophenone, m-aminobenzamide, o-aminobenzamide, 15 p-aminobenzamide, p-amino-N-methylbenzamide, 3-amino-4 methylbenzamide, 3 -amino-4-methoxybenzamide, 3-amino-4 chlorobenzamide, carbamoylanilines (e.g. p-(N-phenyl carbamoyl)aniline, p-[N-(4-chlorophenyl)carbamoyl] aniline, p-[N-(4-aminophenyl)carbamoyl]aniline, 2 20 methoxy-5-(N-phenylcarbamoyl)aniline, 2-methoxy-5-[N (2'-methyl-3'-chlorophenyl)carbamoyl]aniline and 2 methoxy-5-[N-(2'-chlorophenyl)carbamoyl]aniline), 5 acetylamino-2-methoxyaniline, 4-acetylaminoaniline, 4 (N-methyl-N-acetylamino)aniline, 2,5-diethoxy-4-(N 25 benzoylamino)aniline, 2,5-dimethoxy-4-(N-benzoylamino) aniline, 2-methoxy-4-(N-benzoylamino)-5-methylaniline, sulfamoylanilines (e.g. 4-sulfamoylaniline, 3 sulfamoylaniline, 2 -chloro-5-N-phenylsulfamoylaniline, 169 2-methoxy-5-N,N-diethylsulfamoylaniline and 2,5 dimethoxy-4-N-phenysulfamoylaniline), 2-(N-ethyl-N phenylaminosulfonyl)aniline, 4-dimethylamino sulfonylaniline, 4-diethylaminosulfonylaniline, 5 sulfathiazole, 4-aminodiphenyl sulfone, 2-methoxy-5 benzylsulfonylaniline, 2-phenoxysulfonylaniline, 2-(2' chlorophenoxy)sulfonylaniline, 3-anilinosulfonyl-4 methylaniline, nitro-substituted anilines (e.g. o chloro-p-nitroaniline, o-nitro-p-chloroaniline, 2,6 10 dichloro-4-nitroaniline, 5-chloro-2-nitroaniline, o nitroaniline, m-nitroaniline, p-nitroaniline, 2-methyl 4-nitroaniline, m-nitro-p-toluidine and 2-amino-5 nitrobenzonitrile), p-fluoroaniline, o-fluoroaniline, 3-chloro-4-fluoroaniline, 2,4-difluoroaniline, 2,3,4 15 trifluoroaniline, m-aminobenzotrifluoride, 2-amino-3 bromo-5-nitrobenzonitrile, etc. As the aniline derivative, there may also be used aniline derivatives having one or more substi tuents including carboxyl group, nitroso group, 20 oxyamino group, nitroamino group, hydrazino group, ureido group, isocyanate group, mercapto group, sulfo group, etc. The dihydroxy compound of the general formula (XVI) which is usable for synthesizing the urea 25 urethane compound of the formula (VI) includes diphenols such as 2,2-bis(4-hydroxyphenyl)propane, 2,2 bis(hydroxyphenyl)butane, 2,2-bis(hydroxyphenyl) pentane, 2,2-bis(hydroxyphenyl)heptane, 4,4'-biphenol, 170 butyl bis(4-hydroxyphenyl)acetate, benzyl bis(4 hydroxyphenyl)acetate, bis(4-hydroxyphenyl) sulfone, bis(3-methyl-4-hydroxyphenyl) sulfone, bis(3,5 dimethyl-4-hydroxyphenyl) sulfone, bis(2-allyl-4 5 hydroxyphenyl) sulfone, bis(2-methyl-3-tert-butyl-4 hydroxyphenyl) sulfide, 4,4'-dihydroxydiphenyl ether, 4,4'-thiodiphenol, 4,4'-dihydroxybenzophenone, 2,2 bis(4-hydroxyphenyl)hexafluoropropane, 4,4' dihydroxydiphenylmethane, 3,3'-dihydroxydiphenylamine, 10 bis(4-hydroxy-3-methylphenyl) sulfide, etc. However, as such diphenols, those having an amino group are not desirable. Since the amino group has a higher reactivity towards an isocyanate group than does an OH group, the amino group reacts with the isocyanate group 15 before the OH group, so that it is difficult in some cases to obtain the desired compound. A process for synthesizing the urea-urethane compound of the formula (VII) used in each of the twenty-first and twenty-second aspects of the present 20 invention is not particularly limited. This compound can be obtained, for example, by reacting an OH group containing compound of the general formula (IX) with an isocyanate compound of the general formula (XII) and an amine compound of the general formula (XI) according 25 to, for instance, the following reaction formula (L).
171 0 11 H X-OH + OCN-Y-NCO -0 X-0-C-N-Y-NCO o a a(L) 11 H 11 H H i H X-0-C-N-Y-NCO + Z-NH 2 -+ X-0-C-N-Y-N-C-N-Z As the substituent of X bonded to the urethane group of the urea-urethane compound of the general formula (VII), alkyl groups, alkenyl groups, phenyl group, cycloalkyl groups, amide group, alkoxyl 5 groups, nitro group, nitroso group, nitrile group, toluenesulfonyl group, methanesulfonyl group, acetyl group, halogen atoms, formyl group, dialkylamino groups and isocyanate group are preferable. Of such urea-urethane compounds of the 10 general formulas (I) to (VII) as developer, compounds of the general formulas (II) to (VI) are preferable and compounds of the general formulas (V) and (VI) are especially preferable. Furthermore, a compound of the following 15 structural formula (XX) or (XXI) is especially preferable. H3C NC -N y-CN CH3 , NH HN. O
(XX)
172
CH
3 03
H
3 C (XXI) N- O O- H3C O NH CH 3 HN O NH bH 0 In the case of the urea-urethane compound used as developer in each of the twenty-first and twenty-second aspects of the invention and the compounds of the formulas (I) to (IV) and (VII) as 5 developer, if a residue bonded to their urea group or urethane group is an aliphatic compound residue, the coloring density and the print-preserving capability are deteriorated in some cases. Therefore, the residue bonded to the urea group or urethane group is prefer 10 ably an aromatic compound residue or a heterocyclic compound residue. However, the deterioration of the coloring density and the print-preserving capability which is likely to be caused by the introduction of the aliphatic compound residue is reduced by an increase in 15 the total number of urea group(s) and urethane group(s) . In the case of compounds of the formula (III) and the formula (IV), even if an aliphatic compound residue is among residues bonded to the urea group(s) or urethane group(s), almost no problem about 20 performance characteristics is caused. The urea-urethane compound used in each of 173 the twenty-first and twenty-second aspects of the present invention may be obtained by mixing the isocyanate with the corresponding reactants in an organic solvent or without a solvent, reacting them, 5 and then collecting the resulting crystals by filtra tion. As each of the reactants, one or more compounds may be used depending on purposes. As the solvent, any solvent may be used so long as it does not react with an isocyanate group and the functional groups of the 10 reactants. The solvent includes, for example, aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, chlorinated aliphatic hydro carbons, chlorinated aromatic hydrocarbons, chlorinated alicyclic hydrocarbons, and ketones. Methyl ethyl 15 ketone, toluene and the like are especially preferable which dissolve the isocyanate and in which the reaction product has a low solubility. The reaction product obtained by the above reaction procedure is not always a single compound, but is obtained as a mixture of 20 compounds different in the position of a substituent, in some cases. Specific examples of the urea-urethane compound used in each of the twenty-first and twenty second aspects of the present invention are the follow 25 ing compounds ((E-1) to (E-43)).
174 (E-1) 0 N-C-N -CH 3 HN , R 0 0 (E-2) 0 K) N-C-N H H N o OCH 3 0 (E-3) 0 -~ HN, Co 0 0CH3 (E-4) 0
H
1 1 H CH N- C-N H N, Co 0
CH
3 175 (E-5) 1 H N, Co 0 0 CI (E-6)
H
3 CO- N-C-N CH 3 H N, Co 0 0 (E-7) HO HCO 0-C-N CH 3 HN, Co b 176 (E-9) 0 HCO 0-C-N-C-H HN HN~ CO
OCH
3 (E-10) 0 HN O-C-N
CH
3 Co
CH
3 (E-11)0 0--N -CH 3 (E-12) Q0-C-N
CH
3 HH N o
NHCH
177 (E-13)0 "H c1I:: CH 3 HN, CO NH
H
3 CO c N, (E-14)0 H CN-CH 3 K) &CN HNCN 00 C) 11
HN-C-CH
3 (E-15)0 0-. HH H2N-C 0 H Va H2H 11' (E- 16) 0 H3C Q) -C-Nti CH NH NH' c \\~o 01C., 00 (E-17) CH 3
H
3 C 00 178 (E-18)0 C\
H
3 Ca N N\C)Na C H 3 CC N 0 C) (E-19)
CH
3 CH 3 00 11H H1 N-C-NNC-0 OH 0 CC 0 0 0 O 0 (E-20)
CH-
3 S 0 0 N NH Q QHN~ ,0 00 O00 (E-21) 0 0
H
3 C- N-C-N NCNy ,) OH 3 C 0 0 0 0) 03 179 (E-22) CH 3 H3C 0 0, H 0HN. /0 0p 0 o 0 (E-23) CH 3 00 H HN I0 600 (E-24) 00 0NH HN. 4 0 0 0 (E-25)
H
3 C 0 0 H 0\d NH HN. 40
I
180 (E-2 6) HCN /H NH Q N 40 I c' 00 0b (E-27) H H \O H H 9 H~ H)rkCN (E-28) CH3
H
3 C CH Q' N0 'C, 00 (E-29) O 3 OH ,d r\H
H
3 C0 HN. I0c (E-30)
CH-
3 H 3 C 0~N0
C
3 HN0, dHH (E-31)
CH
3 H0 0 c~0 H03~ 0 CH H O- CH 3 a HN. 0,_6N HNC' NN (E-32) 0
H
3 a 0 H3C HN-0 OQ~Q -C-N Q CH3 H CN 3 H 0 (E-33)
H
3 C0 0 0 H O N-&0 QjQ 0-C-N ocNH 0 NHN 0 182 (E-34)
H
3 C O CH 3 QH Q GH2 0 H~ 0~NH HN. ,O0 NH NH (E-35) 0 (E-36) 11 N- C C 2IH- jj H H O -O H' 0 0 (E-37) 0 0N 0 c T8-NC0-40 (E-38) N- -O N O--N- 0 (E-39) N- NN- -OO--N-- 183 (E-40) 00 0 N- - N -O H H-G aOiO 2C2 0 (E-41)
H
3 C H3C N-C - H H H 0 \J HM 0 ONH HN O NH HN 11 -C' 0HN (E-42) 0H 3 C H
CH
3 H 0 NHN NHl HN oHN Q -NCO (E-43)
CH
3 C N
-H
3 C H3C -O>CK> 0 N-K NH HN O/9 NH
NH
2 184 (E-44) O-- _CH3 NH dc NH
CH
2
CH
3 The urea-urethane compound used as developer in the present invention is usually a colorless or light-colored compound that is solid at ordinary temperatures. 5 The molecular weight of the urea-urethane compound used as developer in the present invention is preferably 5,000 or less, more preferably 2,000 or less. The total number of urea group(s) and 10 urethane group(s) in the urea-urethane compound used as developer in the present invention is preferably 20 or less, more preferably 10 or less. The ratio of urea group(s) to urethane group(s) in the molecular struc ture of the urea-urethane compound is preferably 1 : 3 15 to 3 : 1, in particular, 1 : 2 to 2 : 1. For producing a recording material by using the urea-urethane compound as developer, the urea urethane compound of one kind or, if necessary, a combination of the urea-urethane compounds of two or 20 more kinds may be used. When used in a heat-sensitive recording material, the urea-urethane compound is preferably one that has a melting point. The melting point of the 185 urea-urethane compound used as developer in the present invention ranges preferably from 40 0 C to 500 0 C, in particular, from 60 0 C to 300 0 C. The colorless or light-colored dye precursor 5 used in the twenty-second aspect of the present invention is a compound well known as a color former used in pressure-sensitive recording materials and heat-sensitive recording materials and is not particularly limited. As the dye precursor, leuco dyes 10 are especially preferable, and triarylmethane type leuco dyes, fluoran type leuco dyes, fluorene type leuco dyes, diphenylmethane type leuco dyes and the like are more preferable. Typical examples of the leuco dyes are given below. 15 (1) Triarylmethane type compounds 3, 3-bis (p-dimethylaminophenyl) -6-dimethyl aminophthalide (Crystal Violet lactone), 3,3-bis(p dimethylaminophenyl)phthalide, 3-(p-dimethylamino phenyl)-3-(1,2-dimethylindol-3-yl)phthalide, 3-(p 20 dimethylaminophenyl)-3-(2-methylindol-3-yl)phthalide, 3-(p-dimethylaminophenyl)-3-(2-phenylindol-3 yl)phthalide, 3,3-bis(1,2-dimethylindol-3-yl)-5 dimethylaminophthalide, 3,3-bis(1,2-dimethylindol-3 yl)-6-dimethylaminophthalide, 3,3-bis(9-ethylcarbazol 25 3-yl)-5-dimethylaminophthalide, 3,3-bis(2-phenylindol 3-yl)-5-dimethylaminophthalide, 3-p-dimethylamino phenyl-3-(1-methylpyrrol-2-yl)-6- dimethylamino phthalide, etc.
186 (2) Diphenylmethane type compounds 4,4'-bis-dimethylaminophenylbenzhydryl benzyl ether, N-halophenylleucoauramines, N-2,4,5-trichloro phenylleucoauramine, etc. 5 (3) Xanthene type compounds Rhodamine B anilinolactam, Rhodamine B-p chloroanilinolactam, 3-dimethylamino-6-methyl-7-(m trifluoromethylanilino)fluoran, 3-diethylamino-6 methyl-fluoran, 3-diethylamino-7-methyl-fluoran, 3 10 diethylamino-7-chloro-fluoran, 3-diethylamino-7 dibenzylaminofluoran, 3-diethylamino-6-methyl-7 chlorofluoran, 3-diethylamino-7-octylaminofluoran, 3 diethylamino-7-phenylfluoran, 3-diethylamino-6-methyl 7-anilinofluoran, 3-diethylamino-6-methyl-7-p 15 methylanilinofluoran, 3-diethylamino-6-chloro-7 methylfluoran, 3-diethylamino-7-(3,4-dichloroanilino) fluoran, 3-diethylamino-7-(2-chloroanilino)fluoran, 3 diethylamino-6-methyl-7-(o,p-dimethylanilino)fluoran, 3-(N-ethyl-N-tolyl)amino-6-methyl-7-phenethylfluoran, 20 3-diethylamino-7-(4-nitroanilino)fluoran, 3-diethyl amino-6-methyl-7-(m-trifluoromethylanilino)fluoran, 3 diethylamino-6-methyl-7-(o-chloroanilino)fluoran, 3 diethylamino-6-methyl-7-(p-chloroanilino)fluoran, 3 diethylamino-6-methyl-7-(o-fluoroanilino)fluoran, 3 25 diethylamino-6-methyl-7-(p-n-butylanilino)fluoran, 3 diethylamino-6-methyl-7-n-octylaminofluoran, 3 diethylamino-6-chloro-7-anilinofluoran, 3-diethylamino 6-ethoxyethyl-7-anilinofluoran, 3-diethylamino- 187 benzo[a]fluoran, 3-diethylamino-benzo[c]fluoran, 3 diethylamino-6-methyl-7-benzylaminofluoran, 3 diethylamino-6-methyl-7-dibenzylaminofluoran, 3 diethylamino-7-di(p-methylbenzyl)aminofluoran, 3 5 diethylamino-6-methyl-7-diphenylmethylaminofluoran, 3 diethylamino-7-dinaphthylmethylaminofluoran, 10 diethylamino-4-dimethylaminobenzo[a]fluoran, 3 diethylamino-7,8-benzfluoran, 3-diethylamino-6-methyl 7-(m-trichloroanilino)fluoran, 3-diethylamino-7-(o 10 chloroanilino)fluoran, 3-dibutylamino-7-(o-chloro anilino)fluoran, 3-diethylamino-6-methyl-7-(2',4' dimethylanilino)fluoran, 3-(N,N-diethylamino)-5-methyl 7-(N,N-dibenzylamino)fluoran, 3-morpholino-7-(N propyltrifluoromethylanilino)fluoran, 3-pyrrolidino-7 15 trifluoromethylanilinofluoran, 3-diethylamino-5-chloro 7-(N-benzyl-trifluoromethylanilino)fluoran, 3 pyrrolidino-7-(di-p-chlorophenyl)methylaminofluoran, 3 diethylamino-5-chloro-7-(a-phenylethylamino)fluoran, 3 (N-ethyl-N-p-toluidino)-7-((a-phenylethylamino)fluoran, 20 3-diethylamino-7-(o-methoxycarbonylphenylethyl)fluoran, 3-diethylamino-5-methyl-7-(a-phenylethylamino)fluoran, 3-diethylamino-7-piperidinoaminofluoran, 2-chloro-3-(N methyltoluidino)-7-(p-N-butylanilino)fluoran, 3-(N ethyl-N-cyclohexylamino)-5,6-benzo-7-a-naphthylamino 25 4'-bromofluoran, 3-diethylamino-6-methyl-7-mesitidino 4',5'-benzofluoran, 3-dibutylamino-6-methyl-fluoran, 3 dibutylamino-6-methyl-7-chlorofluoran, 3-dibutylamino 6-methyl-7-anilinofluoran, 3-dibutylamino-6-methyl-7-p- 188 methylanilinofluoran, 3-dibutylamino-6-methyl-7-(o,p dimethylanilino)fluoran, 3-dibutylamino-6-methyl-7-(m trifluoromethylanilino)fluoran, 3-dibutylamino-6 methyl-7-(o-chloroanilino)fluoran, 3-dibutylamino-6 5 methyl-7-(p-chloroanilino)fluoran, 3-dibutylamino-6 methyl-7-(o-fluoroanilino)fluoran, 3-dibutylamino-6 methyl-7-(p-n-butylanilino)fluoran, 3-dibutylamino-6 methyl-7-n-octylaminofluoran, 3-dibutylamino-6-chloro 7-anilinofluoran, 3-dibutylamino-6-ethoxyethyl-7 10 anilinofluoran, 3-di-n-pentylamino-6-methyl-7-anilino fluoran, 3-di-n-pentylamino-6-methyl-7-(o,p-dimethyl anilino)fluoran, 3-di-n-pentylamino-6-methyl-7-(m trifluoromethylanilino)fluoran, 3-di-n-pentylamino-6 methyl-7-(o-chloroanilino)fluoran, 3-di-n-pentylamino 15 6-methyl-7-(p-chloroanilino)fluoran, 3-di-n pentylamino-6-methyl-7-(o-fluoroanilino)fluoran, 3 pyrrolidino-6-methyl-7-anilinofluoran, 3-piperidino-6 methyl-7-anilinofluoran, 3-cyclohexylamino-6-chloro fluoran, 3-dimethylamino-5,7-dimethylfluoran, 3-(N 20 methyl-N-isoamylamino)-6-methyl-7-anilinofluoran, 3-(N methyl-N-n-propylamino)-6-methyl-7-anilinofluoran, 3 (N-methyl-N-amylamino)-6-methyl-7-anilinofluoran, 3 (N,N-di-n-amylamino)-6-methyl-7-anilinofluoran, 3-(N methyl-N-isopropylamino)-6-methyl-7-anilinofluoran, 3 25 (N-ethyl-N-n-propylamino)-6-methyl-7-anilinofluoran, 3 (N-ethyl-N-isopropylamino)-6-methyl-7-anilinofluoran, 3-(N-ethyl-N-n-butylamino)-6-methyl-7-anilinofluoran, 3-(N-ethyl-N-isobutylamino)-6-methyl-7-anilinofluoran, 189 3-(N-ethyl-N-n-hexylamino)-6-methyl-7-p-methylanilino fluoran, 3-(N-ethyl-N-n-hexylamino)-6-methyl-7-(o,p dimethylanilino)fluoran, 3-(N-ethyl-N-n-hexylamino)-6 methyl-7-(m-trifluoromethylanilino)fluoran, 3-(N-ethyl 5 N-n-hexylamino)-6-methyl-7-(o-chloroanilino)fluoran, 3 (N-ethyl-N-isoamylamino)-6-methyl-7-anilinofluoran, 3 (N-ethyl-N-isoamylamino)-6-chloro-7-anilinofluoran, 3 (N-ethyl-N-3-methylbutylamino)-6-methyl-7-anilino fluoran, 3-(N-ethyl-N-p-toluidino)-6-methyl-7-anilino 10 fluoran, 3-(N-ethyl-N-p-toluidino)-6-methyl-7-(p methylanilino)fluoran, 3-(N-ethyl-N-p-toluidino)-6 methyl-7-(o,p-dimethylanilino)fluoran, 3-(N-ethyl-N tetrahydrofurfurylamino)-6-methyl-7-anilinofluoran, 3 (N-cyclohexyl-N-methylamino)-6-methyl-7-anilinofluoran, 15 3-(N-cyclohexyl-N-methylamino)-7-anilinofluoran, 3-(N ethyl-N-3-methoxypropylamino)-6-methyl-7-anilino fluoran, 3-(N-ethyl-N-3-ethoxypropylamino)-6-methyl-7 anilinofluoran, 2-(4-oxahexyl)-3-dimethylamino-6 methyl-7-anilinofluoran, 2-(4-oxahexyl)-3-diethylamino 20 6-methyl-7-anilinofluoran, 2-(4-oxahexyl)-3-dipropyl amino-6-methyl-7-anilinofluoran, 3,6-bis(diethylamino) fluoran-y- (2'-nitro) anilinolactam, 3,6-bis(diethyl amino) fluoran-y- (3'-nitro) anilinolactam, 3,6 bis (diethylamino) fluoran-y- (4'-nitro) anilinolactam, 25 3,6-bis(diethylamino)fluoran-y-anilinolactam, etc. (4) Thiazine type compounds benzoylleucomethylene blue, p-nitrobenzoyl leucomethylene blue, etc.
190 (5) Spiro-compounds 3-methylspirodinaphthopyran, 3-ethylspiro dinaphthopyran, 3,3-dichlorospirodinaphthopyran, 3 benzylspirodinaphthopyran, 3-methylnaphtho-(3-methoxy 5 benzo)spiropyran, 3-propylspirobenzopyran, etc. The leuco dyes also includes, for example, the following compounds that can absorb a near infrared ray: 3,6-bis(dimethylamino)fluorene-9-spiro-3'-(6' dimethylamino-phthalide), 3-diethylamino-6-dimethyl 10 aminofluorene-9-spiro-3'-(6'-dimethylaminophthalide), 3,6-bis(diethylamino)fluorene-9-spiro-3'-(6' dimethylaminophthalide), 3-dibutylamino-6-dimethyl aminofluorene-9-spiro-3'-(6'-dimethylaminophthalide), 3-dibutylamino-6-diethylaminofluorene-9-spiro-3'-(6' 15 dimethylaminophthalide), 3,6-bis(dimethylamino) fluorene-9-spiro-3'-(6'-diethylaminophthalide), 3 diethylamino-6-dimethylaminofluorene-9-spiro-3'-(6' diethylaminophthalide), 3-dibutylamino-6-dimethyl aminofluorene-9-spiro-3'-(6'-diethylaminophthalide), 20 3,6-bis(diethylamino)fluorene-9-spiro-3'-(6' diethylaminophthalide), 3,6-bis(dimethylamino)fluorene 9-spiro-3'-(6'-dibutylaminophthalide), 3-dibutylamino 6-diethylaminofluorene-9-spiro-3'-(6'-diethylamino phthalide), 3-diethylamino-6-dimethylaminofluorene-9 25 spiro-3'-(6'-dibutylaminophthalide), 3,3-bis[2-(4 dimethylaminophenyl)-2-(4-methoxyphenyl)ethenyl] 4,5,6,7-tetrachlorophthalide, etc. Of the above-exemplified leuco dyes, the 191 triarylmethane type leuco dyes, fluoran type leuco dyes, fluorene type leuco dyes and diphenylmethane type leuco dyes are preferable from the viewpoint of sensitivity and plasticizer resistance, and compounds 5 having a structure represented by the following chemical formula (i) or (j) are more preferable: Y2 (i) OC=O wherein both Y 2 and Y 3 are alkyl groups or alkoxyalkyl groups, Y 4 is a hydrogen atom, an alkyl group or an alkoxy group, and each of Y 5 and Y. is a hydrogen atom, 10 a halogen atom, an alkyl group or an alkoxy group; or
R
6 R 5
R
7 C=O (j)
R
8
R
10
R
9 wherein each of R 5 and R, is a group represented by the formula (k) or the formula (1): R11 R15 (k) R12 R14 R13 192 (wherein each of R 11 through R.
5 is a hydrogen atom, a halogen atom, a C,-C alkyl group, a C 1 -C alkoxy group or -NR 6 Rl, wherein each of R 1 . and R 1 , is a Cl-C 8 alkyl group); or {18 N R19i() 5 (wherein each of R 1 , and R 19 is a hydrogen atom, a Cl-C alkyl group or a phenyl group), and each of R 7 through
R
10 is a hydrogen atom, a halogen atom, a Cl-C alkyl group, a C,-C 8 alkoxy group or -NR 20
R
21 wherein each of R 20 and R 21 is a Cl-C 8 alkyl group. 10 Such colorless or light-colored dye precursors may be used in combination of two or more thereof if necessary. The urea-urethane compound as developer is used in a proportion of preferably 5 to 1,000 parts by 15 weight, more preferably 20 to 500 parts by weight, per 100 parts by weight of the colorless or light-colored dye precursor. As the proportion of the urea-urethane compound as developer, 5 parts by weight or more is sufficient to allow the dye precursor to develop a 20 color. At such a proportion, the coloring density is high. When the proportion of the urea-urethane compound as developer is 1,000 parts by weight or less, the urea-urethane compound as developer hardly remains as a surplus, and this is economically advantageous and 193 hence preferable. As the urea-urethane compound or urea urethane composition used as developer in the nineteenth aspect of the present invention, any of the 5 urea-urethane compounds of the first to fourth aspects of the present invention or any of the urea-urethane compositions of the fifth to twelfth aspects of the present invention can be used. Synthesis processes of these compounds and compositions are as already 10 described in detail in the explanations of the first to twelfth aspects of the present invention. The incorporation of an isocyanate compound into the color-producing composition of the present invention improves the shelf stability of the composi 15 tion. The isocyanate compound incorporated into the color-producing composition of the present invention refers to a colorless or light-colored, aromatic or heterocyclic isocyanate compound that is solid at ordinary temperatures. For example, one or more of the 20 following isocyanate compounds are used. The isocyanate compound incorporated includes 2,6-dichlorophenyl isocyanate, p-chlorophenyl isocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, 1,3-dimethylbenzene-4,6-diisocyanate, 25 1,4-dimethylbenzene-2,5-diisocyanate, 1-methoxybenzene 2,4-diisocyanate, 1-methoxybenzene-2,5-diisocyanate, 1 ethoxybenzene-2,4-diisocyanate, 2,5-dimethoxybenzene 1,4-diisocyanate, 2,5-diethoxylbenzene-1,4- 194 diisocyanate, 2,5-dibutoxybenzene-1,4-diisocyanate, azobenzene-4,4'-diisocyanate, diphenyl ether-4,4' diisocyanate, naphthalene-1,4-diisocyanate, naphthalene-1,5-diisocyanate, naphthalene-2,6 5 diisocyanate, naphthalene-2,7-diisocyanate, 3,3' dimethyl-biphenyl-4,4'-diisocyanate, 3,3'-dimethoxy biphenyl-4,4'-diisocyanate, diphenylmethane-4,4' diisocyanate, diphenyldimethylmethane-4,4' diisocyanate, benzophenone-3,3'-diisocyanate, fluorene 10 2,7-diisocyanate, anthraquinone-2,6-diisocyanate, 9 ethylcarbazole-3,6-diisocyanate, pyrene-3,8 diisocyanate, naphthalene-1,3,7-triisocyanate, biphenyl-2,4,4'-triisocyanate, 4,4',4"-triisocyanato 2,5-dimethoxytriphenylamine, 4,4',4"-triisocyanato 15 triphenylamine, p-dimethylaminophenyl isocyanate, tris(4-phenylisocyanato)thiophosphate, etc. If necessary, these isocyanates may be used in the form of a so-called block isocyanate, i.e., an addition compound with a phenol, lactam, oxime or the like, they 20 may be used in the form of a diisocyanate dimer such as 1-methylbenzene-2,4-diisocyanate dimer, or a diiso cyanurate trimer as an isocyanurate, and they may be used in the form of a polyisocyanate obtained as an adduct by the use of any of various polyols and the 25 like. There may also be used water adduct isocyanates of 2,4-toluene diisocyanate, diphenylmethane diisocyanate and the like, such as 1,3-bis(3 isocyanato-4-methylphenyl)urea; polyol adducts such as 195 trimethylolpropane adduct of toluene diisocyanate (Desmodule L, a trade name); phenol adduct isocyanates; amine adduct isocyanates; and the isocyanate compounds and isocyanate adduct compounds described in the 5 specification of JP-A-10-76757 and the specification of JP-A-10-95171. The isocyanate compound is used in a propor tion of preferably 5 to 500 parts by weight, more preferably 20 to 200 parts by weight, per 100 parts by 10 weight of the colorless or light-colored dye precursor. When the proportion of the isocyanate compound is 5 parts by weight or more, a sufficient improving effect on the shelf stability can be obtained and the coloring density is high. When the proportion of the isocyanate 15 compound is 500 parts by weight or less, the isocyanate compound hardly remains as a surplus, and this is economically advantageous and hence preferable. The incorporation of an imino compound into the color-producing composition of the present 20 invention further improves the shelf stability. The imino compound that can be incorporated into the color-producing composition of the present invention is a colorless or light-colored compound that has at least one imino group and is solid at ordinary 25 temperatures. Two or more imino compounds may be incorporated in combination, depending on purposes. As the imino compound, those described in JP-A-9-142032 can be mentioned, and the contents of this reference 196 are hereby incorporated herein by reference. Of the imino compounds described in the reference, imino isoindoline derivatives are preferable, and 1,3 diimino-4,5,6, 7 -tetrachloroisoindoline, 3-imino 5 4,5,6, 7 -tetrachloroisoindolin-1-one and 1,3-diimino 4,5,6, 7 -tetrabromoisoindoline are more preferable. The imino compound is used in a proportion of preferably 5 to 500 parts by weight, more preferably 20 to 200 parts by weight, per 100 parts by weight of the 10 colorless or light-colored dye precursor. When the proportion of the imino compound is 5 parts by weight or more, an improving effect on the shelf stability is obtained. When the proportion of the imino compound is 500 parts by weight or less, the imino compound hardly 15 remains as a surplus, and this is economically advantageous and hence preferable. In addition, the incorporation of an amino compound into the color-producing composition of the present invention improves the preservability of an 20 original recording material surface and print. The amino compound that can be incorporated is a colorless or light-colored substance having at least one primary, secondary or tertiary amino group. As such an amino compound, those described in JP-A-9-142032 can be 25 mentioned. Of the amino compounds described in this reference, aniline derivatives having at least one amino group and represented by the following formula (VIII) are especially preferable: 197
R
1 1 X 2
R
3 RR RR (VTII) wherein R 1 , R 2 , R 3 and R 4 are independently a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or an amino group, X, and X 2 are independently an amino group or a group represented by the formula (b): -- O NH2 (b) 5 and Yi is any of -So 2 -, -0-, - (S) n-, - (CH 2 ) n-, -co-, -CONH- and a group represented by any of the formulas (a): 198
CH
3
CH
3
CH
3
CH
3 - 1 1 ) 1- (a)
OH
3
-
3 0 11 or is absent, and n is 1 or 2. These amino compounds may be used singly or as a mixture thereof. For improving the print preservability in the plasticizer resistance, the 5 proportion of the amino compound is preferably 1 to 500 parts by weight per 100 parts by weight of the color less or light-colored dye precursor. When the content 199 of the amino compound is 1 part by weight or more per part of the urea-urethane compound, the print preservability can be improved. When the content is 500 parts by weight or less, performance character 5 istics of the resulting composition can be sufficiently improved and such a content is advantageous from the viewpoint of cost. The incorporation of also an acidic developer into the color-producing composition of the present 10 invention improves the sensitivity and enables the color-producing composition to produce a brilliant color. As the acidic developer that is used when the color-producing composition of the present invention is 15 used in a heat-sensitive recording material, conven tional electron-accepting materials are used and, in particular, phenol derivatives; aromatic carboxylic acid derivatives or their metal compounds; salicylic acid derivatives or their metal salts; N,N-diaryl 20 thiourea derivatives; sulfonylurea derivatives; etc. are preferable. The phenol derivatives are especially preferable. Specific examples of the phenol deriva tives are 2,2-bis(4-hydroxyphenyl)propane, 2,2 bis(hydroxyphenyl)butane, 2,2-bis(hydroxyphenyl) 25 pentane, 2,2-bis(hydroxyphenyl)heptane, 1,1-bis(4 hydroxyphenyl)cyclohexane, butyl bis(4-hydroxyphenyl) acetate, benzyl bis(4-hydroxyphenyl)acetate, bis(4 hydroxyphenyl) sulfone, bis(3-methyl-4-hydroxyphenyl) 200 sulfone, 4-hydroxyphenyl-4'-methylphenyl sulfone, 3 chloro-4-hydroxyphenyl-4'-methylphenyl sulfone, 3,4 dihydroxyphenyl-4'-methylphenyl sulfone, 4-isopropyl phenyl-4'-hydroxyphenyl sulfone, 4-isopropyloxyphenyl 5 4'-hydroxyphenyl sulfone, bis(2-allyl-4-hydroxyphenyl) sulfone, 4-hydroxyphenyl-4'-benzyloxyphenyl sulfone, 4 isopropylphenyl-4'-hydroxyphenyl sulfone, bis(2-methyl 3-tert-butyl-4-hydroxyphenyl) sulfide, methyl 4 hydroxybenzoate, benzyl 4-hydroxybenzoate, (4' 10 chlorobenzyl) 4-hydroxybenzoate, ethyl 1,2-bis(4' hydroxybenzoate), pentyl 1,5-bis(4'-hydroxybenzoate), hexyl 1,6-bis(4'-hydroxybenzoate), dimethyl 3-hydroxy phthalate, stearyl gallate, lauryl gallate, etc. The salicylic acid derivatives include 4-n-octyloxy 15 salicylic acid, 4-n-butyloxysalicylic acid, 4-n pentyloxysalicylic acid, 3-n-dodecyloxysalicylic acid, 3-n-octanoyloxysalicylic acid, 4-n-octyloxycarbonyl aminosalicylic acid, 4-n-octanoyloxycarbonylamino salicylic acid, etc. The sulfonylurea derivatives 20 include, for example, compounds containing one or more arylsulfonylaminoureido groups, such as 4,4-bis(p toluenesulfonylaminocarbonylamino)diphenylmethane, 4,4-bis(o-toluenesulfonylaminocarbonylamino)diphenyl methane, 4,4-bis(p-toluenesulfonylaminocarbonylamino) 25 diphenyl sulfide, 4,4-bis(p-toluenesulfonylamino carbonylamino)diphenyl ether, N-(p-toluenesulfonyl)-N' phenylurea, etc. In addition, there may also be used, for example, 4,4'-[oxybis(ethyleneoxy-p-phenylene- 201 sulfonyl)]diphenol and mixtures composed mainly of this compound (e.g. D-90 (a trade name, mfd. by Nippon Soda Co., Ltd.)). Of the above-exemplified acidic developers, 5 2,2-bis(4-hydroxyphenyl)propane, 4-isopropyloxyphenyl 4'-hydroxyphenyl sulfone, bis(3-allyl-4-hydroxyphenyl) sulfone, 2,4'-dihydroxydiphenyl sulfone and 4,4' [oxybis(ethyleneoxy-p-phenylenesulfonyl)]diphenol are especially preferable because they improve sensitivity 10 and make it possible to obtain a heat-sensitive recording material capable of producing a brilliant color. In order to improve fog, the thermal response and the like, it is also possible to add phenolic 15 compounds such as N-stearyl-N'-(2-hydroxyphenyl)urea, N-stearyl-N'-(3-hydroxyphenyl)urea, N-stearyl-N'-(4 hydroxyphenyl)urea, p-stearoylaminophenol, o-stearoyl aminophenol, p-lauroylaminophenol, p-butyrylamino phenol, m-acetylaminophenol, o-acetylaminophenol, p 20 acetylaminophenol, o-butylaminocarbonylphenol, o stearylaminocarbonylphenol, p-stearylaminocarbonyl phenol, 1,1,3-tris(3-tert-butyl-4-hydroxy-6-methyl phenyl)butane, 1,1,3-tris(3-tert-butyl-4-hydroxy-6 ethylphenyl)butane, 1,1,3-tris(3,5-di-tert-butyl-4 25 hydroxyphenyl)butane, 1,1,3-tris(3-tert-butyl-4 hydroxy-6-methylphenyl)propane, 1,2,3-tris(3-tert butyl-4-hydroxy-6-methylphenyl)butane, 1,1,3-tris(3 phenyl-4-hydroxyphenyl)butane, 1,1,3-tris(3-cyclohexyl- 202 4-hydroxy-5-methylphenyl)butane, 1,1,3-tris(3 cyclohexyl-4-hydroxy-6-methylphenyl)butane, 1,1,3 tetra(3-phenyl-4-hydroxyphenyl)propane, 1,1,3,3 tetra(3-cyclohexyl-4-hydroxy-6-methylphenyl)propane, 5 1,1-bis(3-tert-butyl-4-hydroxy-6-methylphenyl)butane, 1,1-bis(3-cyclohexyl-4-hydroxy-6-methylphenyl)butane, etc. The above-mentioned acidic developer is used in a proportion of preferably 5 to 500 parts by weight, 10 more preferably 20 to 200 parts by weight, per 100 parts by weight of the colorless or light-colored dye precursor. When the proportion of the acidic developer is 5 parts by weight or more, the color development of the dye precursor is satisfactory and the coloring 15 density is high. When the proportion of the acidic developer is 500 parts by weight or less, the acidic developer hardly remains, and this is economically advantageous and hence preferable. 20 Also when the color-producing composition of the present invention is used in a pressure-sensitive recording material, the incorporation of an acidic developer into the color-producing composition improves the coloring density and enables the pressure-sensitive 25 recording material to produce a brilliant color. Also as this acidic developer, an electron accepting material is used. The acidic developer includes, for example, inorganic compounds such as acid 203 clay, activated clay, attapulgite, bentonite, zeolite, colloidal silica, magnesium silicate, talc, aluminum silicate, etc.; phenol, cresol, butylphenol, octyl phenol, phenylphenol, chlorophenol, salicylic acid and 5 the like, or aldehyde condensation novolak resins derived therefrom and their metal salts; and salicylic acid derivatives such as 3-isopropylsalicylic acid, 3 phenylsalicylic acid, 3-cyclohexylsalicylic acid, 3,5 di-t-butylsalicylic acid, 3,5-di(a-methylbenzyl) 10 salicylic acid, 3,5-di-t-octylsalicylic acid, 3-methyl 5-benzylsalicylic acid, 3,5-di(a,a-dimethylbenzyl) salicylic acid, 3-phenyl-5-(a, a-dimethylbenzyl) salicylic, etc. and metal salts thereof. The incorporation of also a fluorescent dye 15 into the color-producing composition of the present invention improves the whiteness. As the fluorescent dye to be incorporated into the color-producing composition of the present invention, various well known ones can be used, and there are mentioned 20 stilbene derivatives, coumarin derivatives, pyrazoline derivatives, bisstyrylbiphenyl derivatives, naphthalimide derivatives, bisbenzoxazolyl derivatives, etc. Although the fluorescent dye is not limited to them, diaminostilbenedisulfonic acid derivatives are 25 especially preferable. As to the amount of the fluorescent dye used, the fluorescent dye is made present in an amount of preferably 0.01 to 3 wt%, more preferably 0.1 to 2 wt%, 204 based on the total weight (in terms of solids) of the color-producing composition. When the amount of the fluorescent dye used is more than 3 wt%, the color producing composition is colored in some cases. When 5 the amount is less than 0.01 wt%, the effect of the fluorescent dye on the whiteness is lessened. Next, the color-producing composition of the present invention may contain shelf-stability-imparting agents. The shelf-stability-imparting agents usable in 10 the present invention are additives such as image stabilizing agents, light stabilizers, antioxidants, etc. By using these shelf-stability-imparting agents in combination with a urea-urethane compound 15 developer (i.e. a developer comprising a urea-urethane compound) and a colorless and light-colored dye precursor, the light resistance of the color-producing composition can be improved and a recording material excellent in light resistance can be obtained. 20 The image-stabilizing agents as preferable examples of the shelf-stability-imparting agents used in the present invention include, for example, 1,1,3 tris(2-methyl-4-hydroxy-5-tert-butylphenyl)butane, 1,1,3-tris(2-methyl-4-hydroxy-5-cyclohexylphenyl) 25 butane, hindered phenol compounds [e.g. 4,4' butylidenebis(2-tert-butyl-5-methylphenol), 4,4' thiobis(2-tert-butyl-5-methylphenol), 2,2'-thiobis(6 tert-butyl-4-methylphenol) and 2,2'-methylenebis(6- 205 tert-butyl-4-methylphenol)], 4-benzyloxy-4'-(2 methylglycidyloxy)diphenyl sulfone, 4,4'-diglycidyloxy diphenyl sulfone, 1,4-diglycidyloxybenzene, sodium 2,2'-methylenebis(4,6-di-tert-butylphenyl)phosphate, 2 5 propanol derivatives and salicylic acid derivatives. Usually, these image-stabilizing agents are used in a proportion of preferably 5 to 1,000 parts by weight, more preferably 10 to 500 parts by weight, per 100 parts by weight of the colorless or light-colored dye 10 precursor. When the proportion of the image stabilizing agents is 5 parts by weight or more, the light resistance is good and the coloring density is high. When the proportion of the image-stabilizing agents is more than 1,000 parts by weight, their effect 15 on the light resistance is not heightened and moreover, such a proportion is economically disadvantageous. The light stabilizers as preferable examples of the shelf-stability-imparting agents used in the present invention include, for example, 2-(2'-hydroxy 20 5'-methylphenyl)benzotriazole, 2-(3',5'-di-t-butyl-2' hydroxyphenyl)benzotriazole, 2-(5'-t-butyl-2' hydroxyphenyl)benzotriazole, 2-[2'-hydroxy-5'-(1,1,3,3 tetramethylbutyl)phenyl]benzotriazole, 2-(3',5'-di-t butyl-2'-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3'-t 25 butyl-2'-hydroxy-5'-methylphenyl)-5-chlorobenzo triazole, 2-(2'-hydroxy-4'-octoxyphenyl)benzotriazole, 2-(3',S'-di-t-pentyl-2'-hydroxyphenyl)benzotriazole, 2 (3'-t-butyl-2'-hydroxy-5'-octyloxycarbonylethylphenyl)- 206 5-chlorobenzotriazole and the like; 4-hydroxy-, 4 methoxy-, 4-octoxy-, 4-decyloxy-, 4-dodecyloxy-, 4 benzyloxy-, 4,2',4'-trihydroxy-, 2'-hydroxy-4,4' dimethoxy- or 4-(2-ethylhexyloxy)-2-hydroxybenzophenone 5 derivatives and the like; 4-t-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis(4-t-butylbenzoyl)resorcinol, 2,4-di-t-butylphenyl 3,5-di-t-butyl-4-hydroxybenzoate, hexadecyl 3,5-di-t-butyl-4-hydroxybenzoate and the 10 like; ethyl a-cyano-0,0-diphenylacrylate, isooctyl a cyano-Q,$-diphenylacrylate, methyl a-carbomethoxy cinnamate, methyl a-cyano-$-methyl-p-methoxycinnamate and the like; bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis(2,2,6,6-tetramethyl-4-piperidyl) 15 succinate, bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, bis(l-octyloxy-2,2,6,6-tetramethyl-4 piperidyl) sebacate, bis(1,2,2,6,6-pentamethyl-4 piperidyl) adipate and the like; 4,4'-di-octyloxy oxanilide, 2,2'-diethoxyoxyoxanilide, 2,2'-di-octyloxy 20 5,5'-di-t-butyloxanilide, 2,2'-di-dodecyloxy-5,5'-di-t butyloxanilide, 2-ethoxy-2'-ethyloxanilide, N,N'-bis(3 dimethylaminopropyl)oxanilide, 2-ethoxy-5-t-butyl-2' ethoxyoxanilide and the like; and 2,4,6-tris(2-hydroxy 4-octyloxyphenyl)-1,3,5-triazine, 2-(2-hydroxy-4 25 octyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5 triazine, 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4 dimethylphenyl)-1,3,5-triazine, 2,4-bis(2-hydroxy-4 propyloxyphenyl-6-(2,4-dimethylphenyl)-1,3,5-triazine, 207 2-(2-hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethyl phenyl)-1,3,5-triazine and the like. Usually, these light stabilizers are used in a proportion of prefer ably 5 to 1,000 parts by weight, more preferably 10 to 5 500 parts by weight, per 100 parts by weight of the colorless or light-colored dye precursor. When the proportion of the light stabilizers is 5 parts by weight or more, the light resistance is good and the coloring density is high. When the proportion of the 10 light stabilizers is more than 1,000 parts by weight, their effect on the light resistance is not heightened and moreover, such a proportion is economically disadvantageous. The antioxidants as preferable examples of 15 the shelf-stability-imparting agents used in the present invention include, for example, 2,6-di-t-butyl 4-methylphenol, 2-t-4,6-dimethylphenol, 2,6-di-t-butyl 4-ethylphenol, 2,6-di-t-butyl-4-n-butylphenol, 2,6-di t-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methyl 20 phenol, 2-(a-methylcyclohexyl)-4,6-dimethylphenol, 2,6 dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-dinonyl-4-methylphenol, 2,6-di-t-butyl-4-methoxy methylphenol, 2,4-dimethyl-6-(1'-methyl-undeca-1'-yl) phenol,, 2,4-dimethyl-6-(1'-methyl-heptadeca-l'-yl) 25 phenol, 2,4-dimethyl-6-(l'-methyl-trideca-l'-yl) phenol, and mixtures thereof; 2,4-di-octylthiomethyl-6 t-butylphenol, 2,4-di-octylthiomethyl-6-methylphenol, 2,4-di-octylthiomethyl-6-ethylphenol, 2,6-di-dodecyl- 208 thiomethyl-4-nonylphenol, and mixtures thereof; 2,6-di t-butyl-4-methoxyphenol, 2,5-di-t-butylhydroquinone, 2,5-di-t-amylhydroquinone, 2,6-diphenyl-4-octadecyloxy phenol, 2,6-di-t-butylhydroquinone, 2,5-di-t-butyl-4 5 hydroxyanisole, 3,5-di-t-butyl-4-hydroxyanisole, 3,5 di-t-butyl-4-hydroxyphenyl stearate, bis(3,5-di-t butyl-4-hydroxyphenyl) adipate, and mixtures thereof; 2,4-bis-octylmercapto-6-(3,5-di-t-butyl-4-hydroxy anilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3,5 10 di-t-butyl-4-hydroxyanilino)-1,3,5-triazine, 2 octylmercapto-4,6-bis(3,5-di-t-butyl-4-hydroxyphenoxy) 1,2,3-triazine, 1,3,5-tris(3,5-di-t-butyl-4-hydroxy benzyl)-isocyanurate, 1,3,5-tris(4-t-butyl-3-hydroxy 2,6-dimethylbenzyl)isocyanurate, 2,4,6-tris(3,5-di-t 15 butyl-4-hydroxyphenylethyl)-1,3,5-triazine, 1,3,5 tris(3,5-di-t-butyl-4-hydroxyphenylpropionyl) hexahydro-1,3,5-triazine, 1,3,5-tris(3,5-dicyclohexyl 4-hydroxybenzyl)-isocyanurate and the like; 2,2' methylenebis(6-t-butyl-4-methylphenol), 2,2'-methylene 20 bis(6-t-butyl-4-ethylphenol), 2,2'-ethylidenebis(4,6 di-t-butylphenol), 2,2'-ethylidenebis(6-t-butyl-4 isobutylphenol), 4,4'-methylenebis(2,6-di-t-butyl phenol), 4,4'-methylenebis(6-t-butyl-2-methylphenol), 1,1-bis(5-t-butyl-4-hydroxy-2-methylphenyl)butane, 25 ethylene glycol bis[3,3'-bis(3'-t-butyl-4'-hydroxy phenyl) butyratel and the like; 1,3,5-tris(3,5-di-t butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, 1,4 bis(3,5-di-t-butyl-4-hydroxybenzyl)-2,3,5,6- 209 tetramethylbenzene, 2,4,6-tris(3,5-di-t-butyl-4 hydroxybenzyl)-phenol and the like. Usually, these antioxidants are used in a proportion of preferably 5 to 1,000 parts by weight, more preferably 10 to 500 5 parts by weight, per 100 parts by weight of the colorless or light-colored dye precursor. When the proportion of the antioxidants is 5 parts by weight or more, the light resistance is good and the coloring density is high. When the proportion of the anti 10 oxidants is more than 1,000 parts by weight, their effect on the light resistance is not heightened and moreover, such a proportion is economically disadvantageous. The color-producing composition of the 15 present invention can be made into a recording material by forming a color-producing layer of the composition on some substrate by a method such as coating. The structure of the recording material is varied depending on the kind of the recording material. 20 The color-producing composition of the present invention can be used in any of various record ing materials such as heat-sensitive recording materials, pressure-sensitive recording materials and the like, and is suitable particularly for the heat 25 sensitive recording materials. When the color-producing composition is used in a heat-sensitive recording material, a heat sensitive recording layer capable of producing a color 210 on heating is formed on a substrate. Specifically, the above-mentioned urea-urethane compound, the above mentioned colorless or light-colored dye precursor such as a leuco dye, the heat-meltable material described 5 hereinafter, and the like should be applied on a substrate, each in the form of a dispersion together with other necessary components to form a heat sensitive recording layer. The dispersion is prepared by finely grinding one or more compounds as each of the 10 components described above, with a sand grinder or the like in an aqueous solution containing a compound having dispersing capability, such as a water-soluble polymer, a surfactant or the like. The particle size of each of the dispersions thus obtained is preferably 15 adjusted to 0.1 to 10 pm, in particular, to about 1 pm. Specific examples of the compound having dispersing capability which can be used in the present invention are water-soluble polymers such as poly(vinyl alcohol)s, carboxylic acid-modified poly(vinyl 20 alcohol)s, sulfonic acid-modified poly(vinyl alcohol)s, methyl cellulose, hydroxypropylmethyl cellulose, hydroxypropyl cellulose, etc.; anionic surfactants such as condensed naphthalenesulfonates, polyoxyethylene alkyl ether sulfuric acid ester salts (e.g. sodium 25 polyoxyethylene lauryl ether sulfates, sodium polyoxy ethylene alkyl ether sulfates and sodium polyoxy ethylene alkyl phenyl ether sulfates), dialkylsulfo succinic acid ester sodium, alkylphosphates (e.g.
211 diethanolamine alkylphosphates and potassium alkylphosphates), specialty carboxylic acid-based polymers, etc.; nonionic surfactants such as polyoxy ethylene alkyl ethers, polyoxyethylene alky phenyl 5 ethers, polyoxyethylene sorbitan fatty acid esters, fatty acid monoglycerides, polyethylene glycol fatty acid esters, etc.; and cationic surfactants such as dicyanamidopolyamines, tertiary amine salts, quaternary ammonium salts, etc. Of these, the polyvinyl alcohols, 10 carboxylic acid-modified polyvinyl alcohols, sulfonic acid-modified polyvinyl alcohols and methyl cellulose are especially preferable. The above-exemplified compounds may be used singly or as a mixture thereof. When the urea-urethane compound developer 15 according to the present invention is used in a heat sensitive recording material, the adjustment of the average particle size of the urea-urethane compound developer to not more than 5 pm and not less than 0.05 pm makes it possible to obtain a heat-sensitive 20 recording material which has a sufficient color development sensitivity, gives a very stable printed developed color image, and has a good plasticizer resistance. The average particle size is more preferably not more than 3 pm and not less than 0.1 pm. 25 When the average particle size is less than 0.05 pm, the preservability of the original recording material surface against plasticizers is deteriorated. On the other hand, when the average particle size is more than 212 5 pm, the sensitivity of the heat-sensitive recording material is decreased. Particularly when the urea-urethane compound is subjected to wet grinding in an aqueous medium, the 5 temperature of the aqueous medium is preferably 60*C or lower. At the time of the grinding, the urea-urethane compound developer comes into contact with water, so that hydrolysis of its urethane group(s) proceeds depending on conditions. Therefore, the sensitivity of 10 a heat-sensitive recording material obtained by the use of the urea-urethane compound developer tends to be decreased. Particularly when the medium temperature at the grinding is higher than 60 0 C, the sensitivity is remarkably decreased. The medium temperature at the 15 grinding is more preferably 40*C or lower. In addition, when the urea-urethane compound developer is ground, it is preferably ground in a neutral pH range of 5 to 10. When the pH at the grind ing is lower than 5, an inorganic pigment and the like 20 are decomposed in the production of a heat-sensitive coating liquid, so that the sensitivity tends to be decreased. On the other hand, when the pH is higher than 10, the urea-urethane compound developer is hydrolyzed, so that the sensitivity is decreased in 25 some cases. Specific examples of dispersing agent usable for preparing a dispersion of the urea-urethane compound developer by grinding in the present invention are water-soluble polymers such as poly(vinyl 213 alcohol)s, carboxylic acid-modified poly(vinyl alcohol)s, sulfonic acid-modified poly(vinyl alcohol)s, methyl cellulose, hydroxypropylmethyl cellulose, hydroxypropyl cellulose, etc.; anionic surfactants such 5 as condensed naphthalenesulfonates, polyoxyethylene alkyl ether sulfuric acid ester salts (e.g. sodium polyoxyethylene lauryl ether sulfates, sodium polyoxy ethylene alkyl ether sulfates and sodium polyoxy ethylene alkyl phenyl ether sulfates), dialkylsulfo 10 succinic acid ester sodium, alkylphosphates (e.g. diethanolamine alkylphosphates and potassium alkyl phosphates), specialty carboxylic acid-based polymers, etc.; nonionic surfactants such as polyoxyethylene alkyl phenyl ethers, polyoxyethylene sorbitan fatty 15 acid esters, fatty acid monoglycerides, polyethylene glycol fatty acid esters, etc.; and cationic surfactants such as dicyanamidopolyamines, tertiary amine salts, quaternary ammonium salts, etc. Of these, the water-soluble polymers and the anionic surfactants 20 are especially preferable because they make it possible to obtain a heat-sensitive recording material that has a high sensitivity irrespective of conditions of dispersing the urea-urethane compound developer and has an improved preservability of the original recording 25 material surface against plasticizers irrespective of the average particle size of the urea-urethane compound developer. The poly(vinyl alcohol)s, modified poly(vinyl alcohol)s, methyl cellulose, hydroxypropyl- 214 methyl cellulose, condensed sodium naphthalene sulfonate, polycarboxylic acid ammonium salts, water soluble low-molecular weight copolymers and sodium 2 ethylhexylsulfosuccinate are more preferable. Of 5 these, methyl cellulose, hydroxypropylmethyl cellulose, condensed sodium naphthalenesulfonate, and water soluble low-molecular weight copolymers are still more preferable, and hydroxypropylmethyl cellulose is the most preferable. The above-exemplified dispersing 10 agents may be used singly or as a mixture thereof. As a dispersing agent usable for preparing a dispersion of the colorless or light-colored dye precursor by grinding in the present invention, the same compounds as those used as the dispersing agent 15 for dispersing the urea-urethane compound developer can be used. Of such compounds, the water-soluble polymers, the anionic surfactants and mixed dispersing agents of these two kinds of the compounds are especially preferable for improving a heat-sensitive 20 recording material in sensitivity and in preservability of the original recording material surface against plasticizers. Mixed dispersing agents consisting of methyl cellulose or hydroxypropylmethyl cellulose as a water-soluble polymer and a polyoxyethylene alkyl ether 25 sulfate or sodium 2-ethylhexylsulfosuccinate as an anionic surfactant are more preferable. A mixed dispersing agent of hydroxypropylmethyl cellulose and sodium 2 -ethylhexylsulfosuccinate is the most 215 preferable. The pH of a coating liquid containing the urea-urethane compound and the colorless or light colored dye precursor is preferably 5 to 12. 5 The heat-sensitive recording layer may contain, besides the components described above, pigments such as diatomaceous earth, talc, kaolin, calcined kaolin, calcium carbonate, magnesium carbonate, titanium oxide, zinc oxide, silicon oxide, 10 aluminum hydroxide, urea-formaldehyde resin, etc. In addition, the heat-sensitive recording layer may, if necessary, contain metal salts of higher fatty acids, such as zinc stearate, calcium stearate, etc.; and waxes such as paraffin, oxidized paraffin, polyethy 15 lenes, oxidized polyethylenes, stearamide, cator wax, etc., for the purpose of, for example, preventing the wear of a head and sticking. If necessary, the heat sensitive recording layer may also contain dispersing agents such as sodium dioctylsulfosuccinate, etc.; 20 ultraviolet absorbers of benzophenone type, benzotriazole type and the like; surfactants; fluorescent dyes; etc. As a binder usable for forming the heat sensitive recording layer, there can be mentioned, for 25 example, water-soluble binders such as starches, hydroxyethyl cellulose, methyl cellulose, carboxymethyl cellulose, gelatin, casein, poly(vinyl alcohol)s, modified poly(vinyl alcohol)s, sodium poly(acrylate)s, 216 acrylamide-acrylic ester copolymers, acrylamide-acrylic ester-methacrylic acid terpolymers, alkali salts of styrene-maleic anhydride copolymers, alkali salts of ethylene-maleic anhydride copolymers, etc.; and latex 5 type water-insoluble binders of styrene-butadiene copolymers, acrylonitrile-butadiene copolymers, methyl acrylate-butadiene copolymers, etc. As the substrate for the heat-sensitive recording layer, paper is mainly used, though any of 10 various woven fabrics, nonwoven fabrics, synthetic resin films, laminated papers, synthetic papers, metal foils, and composite sheets obtained by combining two or more of them may be used besides paper, depending on their purpose. The basis weight of the substrate is 15 preferably 40 g/m 2 to 200 g/m 2 . The substrate is preferably excellent in surface smoothness and flatness because a heat-sensitive recording material obtained by the use of the substrate is desired to have as high a flatness as possible. Therefore, the substrate is 20 preferably subjected to surface treatment by applying heat and pressure by means of any of a machine calender, soft calender, supercalender and the like. The surface pH of the substrate is preferably 3 to 9, more preferably 5 to 9, most preferably 6 to 8. 25 When the surface pH of the substrate is lower than 3, fog tends to occur. When the surface pH of the substrate is higher than 12, the urea-urethane compound developer is decomposed, so that the coloring density 217 is decreased in some cases. The heat-sensitive recording layer may be composed of either a single layer or two or more layers. The heat-sensitive recording layer may have, 5 for example, a multilayer structure formed by incorporating each color-producing component into one layer. A protective layer composed of a single layer or two or more layers may be formed on the heat sensitive recording layer, and an intermediate layer 10 composed of a single layer or two or more layers may also be formed between the substrate and the heat sensitive recording layer. The heat-sensitive recording layer can be obtained by mixing aqueous dispersions prepared by fine grinding of each color 15 producing component or any other component, with a binder and the like, applying the resulting mixture on the substrate, and drying the mixture. The coating amount of this coating liquid is preferably 1 to 15 g/m 2 when the coating liquid is in a dried state. 20 When the color-producing composition of the present invention is used in a heat-sensitive recording material, a heat-meltable material may be incorporated into the color-producing composition in order to improve the sensitivity. The heat-meltable material is 25 preferably one which has a melting point of 60*C to 180 0 C, in particular, one which has a melting point of 80 0 C to 140 0 C. The heat-meltable material includes, for example, benzyl p-benzyloxybenzoate, stearamide or 218 its emulsified product, palmitamide, N-methylol stearamide, -naphthyl benzyl ether, N-stearylurea, N,N'-distearylurea, phenyl $-naphthoate, phenyl 1 hydroxy-2-naphthoate, 0-naphthol (p-methylbenzyl) 5 ether, 1,4-dimethoxynaphthalene, 1-methoxy-4-benzyloxy naphthalene, N-stearoylurea, p-benzylbiphenyl, 1,2 di(m-methylphenoxy)ethane, 1-phenoxy-2-(4-chloro phenoxy)ethane, 1,4-butanediol phenyl ether, dimethyl terephthalate, m-terphenyl, dibenzyl oxalate and (p 10 chlorobenzyl) oxalate. In addition, 4,4'-dimethoxybenzophenone, 4,4'-dichlorobenzophenone, 4,4'-difluorobenzophenone, diphenyl sulfone, 4,4'-dichlorodiphenyl sulfone, 4,4' difluorodiphenyl sulfone, 4,4'-dichlorodiphenyl 15 disulfide, diphenylamine, 2-methyl-4-methoxydiphenyl amine, N,N'-diphenyl-p-phenylenediamine, 1-(N phenylamino)naphthalene, benzil, 1,3-diphenyl-1,3 propanedione, etc. are preferable as the heat-meltable material because they are very effective in improving 20 the sensitivity. As the heat-meltable material, there may also be used benzyl 4-hydroxybenzoate, 4-(benzyloxy)phenol, 2,4-dihydroxybenzophenone, 2,2',4,4'-tetrahydroxybenzo phenone, 4,4'-dihydroxybenzophenone, 2,2-bis(4-hydroxy 25 phenyl)propane, 4,4'-dihydroxydiphenyl sulfone, bis(3 methyl-4-hydroxyphenyl) sulfone, bis(3,5-dimethyl-4 hydroxyphenyl) sulfone, 3,4-dihydroxyphenyl-4' methylphenyl sulfone, bis(2-methyl-3-tert-butyl-4- 219 hydroxyphenyl) sulfide, 4,4'-dihydroxydiphenyl ether, 4,4'-thiodiphenol, 4,4'-dihydroxydiphenylmethane, 3,3' dihydroxydiphenylamine, bis(4-hydroxy-3-methylphenyl) sulfide, 4-hydroxy-4'-isopropoxydiphenyl sulfone, 4,4' 5 thiobisbenzenethiol, salicylanilide, 4,4'-diamino-3,3' diethyldiphenylmethane, 4 ,4'-diaminobenzanilide, 3,3' dichloro-4,4'-diaminodiphenylmethane, 3,3'-dimethyl 4
,
4 '-diaminodiphenylmethane, 4,4'-thiodianiline, 2,2' dithiodianiline, 4,4'-dithiodianiline, 4,4'-diamino 10 diphenyl ether, 3
,
3 '-diaminodiphenyl ether, 3,4' diaminodiphenyl ether, 4,4'-diaminodiphenylmethane, 3,4'-diaminodiphenylmethane, bis(3-amino-4-chloro phenyl) sulfone, bis(3,4-diaminophenyl) sulfone, 4,4' diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, 15 3,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl methane, 4,4'-diaminodiphenylamine, 3,3'-diaminobenzo phenone, 4
,
4 '-diaminobenzophenone, acetoacetic o chloroanilide, acetoacetic anilide, acetoacetic o toluidide, acetoacetic p-toluidide, acetoacetic o 20 anisidide, acetoacetic m-xylidide and p-acetotoluidide, etc. Of these, diphenyl sulfone, di-p-methylbenzyl oxalate, benzil, 0-naphthyl benzyl ether, p-benzyl biphenyl, 1,2-di(m-methylphenoxy)ethane, 1,2-diphenoxy 25 methylbenzene, m-terphenyl and stearamide are prefer ably used. In addition, employment of a heat-meltable material of the following structural formula (XVIII), 220 among the above-exemplified heat-meltable materials, in a heat-sensitive recording material is markedly effec tive in increasing the sensitivity of the recording material and improving the plasticizer resistance of a 5 print portion and the heat resistance of the original recording material surface. Heat-meltable materials represented by the structural formula (XIX) shown below are especially preferable. 0 _Y__0(XVIII) wherein Y is any of -SO 2 -, -(S)n-, -0-, -CO-, -CH 2 -, 10 -CH (C 6
H
5 ) -, -C (CH 3 ) 2-' -COCO-, -C0 3 -, -COCH 2 CO-, -COOCH 2 -, -CONH-, -OCH 2 - and -NH-, n is 1 or 2, and hydrogen atom(s) of each benzene ring may be replaced by a halogen atom, a hydroxyl group, a nitro group, a nitroso group, a nitrile group, an isocyanate group, an 15 isothiocyanate group, a mercapto group, a sulfamoyl group, a sulfone group, an amino group, an aromatic compound residue, an aliphatic compound residue or a heterocyclic compound residue. 0 K (XIX) 0 wherein hydrogen atom(s) of each benzene ring may be 20 replaced by a halogen atom, a hydroxyl group, a nitro group, a nitroso group, a nitrile group, an isocyanate group, an isothiocyanate group, a mercapto group, a 221 sulfamoyl group, a sulfone group, an amino group, an aromatic compound residue, an aliphatic compound residue or a heterocyclic compound residue. The above-exemplified heat-meltable materials 5 may be used singly or as a mixture thereof. For attaining a sufficient thermal response, the heat meltable material is used in a proportion of preferably 10 to 300 parts by weight, more preferably 20 to 250 parts by weight, per 100 parts by weight of the color 10 less or light-colored dye precursor. As a dispersing agent usable for preparing a dispersion of the heat-meltable material by grinding in the present invention, the same compounds as those used as the dispersing agent for dispersing the urea 15 urethane compound developer can be used. Of such compounds, the water-soluble polymers and the anionic surfactants are especially preferable for improving a heat-sensitive recording material in preservability of the original recording material surface against 20 plasticizers. The poly(vinyl alcohol)s, modified poly(vinyl alcohol)s, methyl cellulose, hydroxypropyl methyl cellulose, condensed sodium naphthalene sulfonate, polycarboxylic acid ammonium salts, water soluble low-molecular weight copolymers and sodium 2 25 ethylhexylsulfosuccinate are more preferable. Of these, the modified poly(vinyl alcohol)s, methyl cellulose, hydroxypropylmethyl cellulose, condensed sodium naphthalenesulfonate, polycarboxylic acid 222 ammonium salts are still more preferable, and hydroxypropylmethyl cellulose is the most preferable. The above-exemplified dispersing agents may be used singly or as a mixture thereof. 5 When the urea-urethane compound developer is ground, fine grinding of the developer together with the above-mentioned heat-meltable material (co grinding) further improves the sensitivity and plasticizer resistance of a heat-sensitive recording 10 material as compared with fine grinding of each compound followed by mixing of the ground compounds. The reason why these effects are obtained is not completely clear. Furthermore, the moisture resistance of the 15 non-print portion (the original surface) of a heat sensitive recording material can be improved by using at least one dispersing agent for the urea-urethane compound developer selected from methyl cellulose, hydroxypropylmethyl cellulose, condensed sodium 20 naphthalenesulfonate and water-soluble low-molecular weight copolymers, and at least one dispersing agent for the heat-meltable material selected from modified poly(vinyl alcohol)s, methyl cellulose, hydroxypropyl methyl cellulose, condensed sodium naphthalenesulfonate 25 and polycarboxylic acid ammonium salts. The color-producing composition of the present invention can be used in various heat-sensitive recording materials and is especially suitable for 223 heat-sensitive magnetic recording materials, labels for heat-sensitive recording, multicolor heat-sensitive recording materials, and heat-sensitive recording materials for laser marking. 5 When the color-producing composition of the present invention is used in a heat-sensitive magnetic recording material, the recording material is preferably in the following form: a heat-sensitive recording layer containing the urea-urethane compound 10 developer is formed on one side of a substrate and a magnetic recording layer is formed on the other side. The magnetic recording layer of the heat sensitive magnetic recording material is formed by coating a substrate with a coating material prepared by 15 uniformly dispersing ferromagnetic powder such as barium ferrite, strontium ferrite, Co-y-Fe 2
C
2 , y-Fe 2
(
2 or the like in an aqueous binder such as an aqueous emulsion resin, and drying the coated substrate. In this case, various additives such as antistatic agents 20 (e.g. carbon graphite), lubricants (e.g. wax), color pigments for hue adjustment, coating-film flexibilizers [e.g. poly(ethylene oxide)s], etc. may be added depend ing on their purpose. The heat-sensitive magnetic recording 25 material of the present invention is suitable as heat sensitive magnetic recording materials used as rail road tickets, tickets, prepaid cards, etc. When the color-producing composition of the 224 present invention is used in a label for heat-sensitive recording, the label is preferably in the following form: a heat-sensitive recording layer containing the urea-urethane compound developer is formed on one side 5 of a substrate and an adhesive layer is formed on the other side. The adhesive layer of this heat-sensitive recording material is composed mainly of a pressure sensitive adhesive. The pressure-sensitive adhesive 10 includes, for example, synthetic-rubber-based emulsion type adhesives, acrylic emulsion type adhesives, natural-rubber-based solvent type adhesives, acrylic solvent type adhesives and silicon-based solvent type adhesives. Of these, the acrylic emulsion type 15 adhesives are especially preferable. When a reverse-side layer (a back coating layer) is, if necessary, formed between the adhesive layer and the substrate in the label for heat-sensitive recording produced by a process according to the 20 present invention, taking-out of curl, prevention of electrostatic charge, and adjustment of coefficient of friction are possible in the label for heat-sensitive recording. As the components of a coating liquid for the reverse-side layer, a coating method for the 25 coating liquid, and the like, the same components, method and the like as in the formation of the heat sensitive recording layer may be employed. The dry spread of the coating liquid ranges preferably from 0.2 225 to 10.0 g/m 2 . The order of coating in the production of the label for heat-sensitive recording is not particularly limited. For example, either of the following orders 5 may be employed: the heat-sensitive recording layer is formed on one side of the substrate and then the back coating layer is formed on the other side, after which the adhesive layer is formed on the back coating layer; or the back coating layer is formed on one side of the 10 substrate and then the heat-sensitive recording layer is formed on the other side, after which the adhesive layer is formed on the back coating layer. As to a method for forming the adhesive layer on the back coating layer, a liquid for forming the 15 adhesive layer may be directly applied on the back coating layer and dried, or a material obtained by previously applying a liquid for forming the adhesive layer, on release paper, followed by drying may be attached to the back coating layer side of a heat 20 sensitive recording material having no adhesive layer formed thereon. In addition, the thermal response can be improved by forming an intermediate layer composed of a single layer or two or more layers, between the heat 25 sensitive recording layer and the substrate. The intermediate layer is composed mainly of an organic or inorganic pigment, hollow particles and an aqueous binder such as a water-soluble polymer or a latex. As 226 the organic or inorganic pigment and the aqueous binder, the same organic or inorganic pigment and aqueous binder as used in the heat-sensitive recording layer can be used. A method for forming the inter 5 mediate layer is not particularly limited. As this method, the same method as the method for forming the heat-sensitive recording layer can be adopted. The dry spread for forming the intermediate layer ranges preferably from 2.0 to 15.0 g/m 2 . 10 When the color-producing composition of the present invention is used in a multicolor heat sensitive recording material, this recording material is preferably in the following form: at least two heat sensitive recording layers are formed on one side of a 15 substrate and at least one of said heat-sensitive recording layers contains the urea-urethane compound developer. As the substrate used, there can be used synthetic paper produced by kneading a polyolefin resin 20 and a white inorganic pigment with heating, extruding the kneaded product through a die, stretching the extruded product in a lengthwise direction, laminating one or two films made of a polyolefin resin and a white inorganic pigment on each side of the stretched 25 product, and stretching the resulting assembly in a crosswise direction to make the same semitransparent or opaque; films obtained by kneading one of or a mixture of two or more of thermoplastic resins such as 227 polyethylenes, polypropylenes, ethylene-vinyl acetate copolymer resins, poly(vinyl chloride)s, polystyrenes, polyesters, etc. with heating, extruding the kneaded product through a die, and then stretching the kneaded 5 product biaxially; opaque films obtained by mixing a white inorganic pigment with any of the above exemplified resins, followed by biaxial stretching; and substrates produced from pulp fiber, such as woodfree paper, medium-duty paper, machine glazed paper, 10 regenerated paper, coated paper, etc. The substrates made of pulp fiber are preferably coated with a heat sensitive layer after previous formation of a layer for coating in order to improve the uniformity of image. The heat-sensitive color-producing layer 15 according to the present invention comprises as its main constituents an adhesive and a color-producing composition capable of causing color development reaction owing to the contact of materials with each other made by heating. Specific examples of the color 20 producing composition are combinations of a colorless or light-colored dye precursor and the above-mentioned urea-urethane developer capable of allowing said dye precursor to develop a color, on heating, and combinations of a diazo compound and a coupler capable 25 of developing a color by its reaction with a diazo compound. If necessary, crosslinking agents, pigments and heat-meltable materials may be incorporated into the color-producing composition. Usually, the coating 228 amount of the heat-sensitive color-producing layer is preferably 3 to 15 g/m 2 from the viewpoint of color development sensitivity and coloring density. As a color-developable dye, the colorless or 5 light-colored dye precursor already described is used which can develop a color when reacted with the urea urethane compound developer with heating. On the other hand, in a heat-sensitive recording layer comprising as its main constituents a 10 diazo compound and a coupler capable of developing a color by its reaction with said diazo compound, these compounds are a well-known light-decomposable diazo compound and a coupler capable of forming a pigment by its reaction with said diazo compound. If necessary, a 15 basic material and the like may be added in order to accelerate the reaction of the diazo compound with the coupler. The coupler and the basic material are preferably used as a mixture thereof in proportions of 10 to 1,000 parts by weight and 10 to 2,000 parts by 20 weight, respectively, per 100 parts by weight of the diazo compound. The term "light-decomposable diazo compound" used herein means a diazo type photosensitive material capable of forming a pigment by its reaction with a 25 coupling component on heating, such as a diazonium salt, diazosulfonate compound, diazoamino compound, quinonediazide compound or the like. The diazonium salt refers to a compound represented by the general 229 formula: Ar-N 2 -X~ wherein Ar is an aromatic portion, N 2 ' is a diazonium group, and X~ is a counter anion. Such compounds have 5 various maximum absorption wavelengths, depending on the positions and kinds of substituents of the Ar portion. Specific examples of the diazonium compound used in the present invention are 4-dimethylamino 10 benzenediazonium, 4 -diethylaminobenzenediazonium, 4 dipropylaminobenzenediazonium, 4-methylbenzylamino benzenediazonium, 4 -dibenzylaminobenzenediazonium, 4 ethylhydroxyethylaminobenzenediazonium, 4-diethylamino 2-methoxybenzenediazonium, 4-dimethyl-3-methylbenzene 15 diazonium, 4-benzoylamino-2, 5-diethoxybenzenediazonium, 4 -morpholinobenzenediazonium, 4-morpholino-2, 5 diethoxybenzenediazonium, 4-morpholino-2, 5 dibutoxybenzenediazonium, 4-anilinobenzenediazonium, 4 toluylmercapto-2, 5-diethoxybenzenediazonium, 4- (N,N 20 dioctylcarbamoyl) benzenediazonium, 2-octadecyloxy benzenediazonium, 4-( 4 -tert-octylphenoxy)benzene diazonium, 4- (2, 4 -di-tert-amylphenoxy)benzenediazonium, 2- ( 4 -tert-octylphenoxy)benzenediazonium, 5-chloro-2- (4 tert-octylphenoxy)benzenediazonium, 2,5-bis 25 octadecyloxybenzenediazonium, 2,4-bis-octadecyloxy benzenediazonium, 4-(N-octyllauroylamino)benzene- 230 diazonium, etc. Specific examples of the counter anion of the diazonium salt used in the present invention are Cl-1/2ZaCl;,
BF
4 , PF6, B(ph) 4, CnF 2 nu+COO (n is 3 to 9) CmF 2 m+SO 3 - (m is 2 to 8), (CkF 2 k+ 1 S0 2
)
2 CH~ (k is 1 to 18), 5 etc. The diazosulfonate compound used in the present invention is a compound represented by the general formula: Ar-N 2
-SO
3 Na 10 wherein Ar is an aromatic portion. Specific examples of the diazosulfonate compound used in the present invention are sodium benzenediazosulfonates having one or more substituents including 2-methoxy, 2-phenoxy, 2 methoxy-4-phenoxy, 2,4-dimethoxy, 2-methyl-4-methoxy, 15 2,4-dimethyl, 2,4,6-trimethyl, 2,4,6-trimethoxy, 2,4 dimethoxy-5-chloro, 2-methoxy-5-nitro, 2-methoxy-5 acetamido, 2-methoxy-5-N,N-diethylsulfonamido, 2 methoxy-5-N-phenylcarbamyl, 3-methyl, 4-methyl, 4 methoxy, 4-ethoxy, 4-phenyl, 4-phenoxy, 4-acetamido, 20 etc.; and sodium benzenediazosulfonates having one or more substituents including 4-(N-ethyl-N-benzylamino), 4-(N,N-dimethylamino), 4-(N,N-diethylamino), 4-(NN diethylamino)-3-chloro, 4-(N-ethylamino)-3-methyl, 4 (N,N-diethylamino)-2-methyl, 4-(N-ethyl-N-0-hydroxy 25 ethylamino), 4 -pyrrolidino-3-chloro, 4-pyrrolidino-3,5 dichloro, 4-morpholino, 4 -morpholino-3-chloro, 4 morpholino-2-methoxy, 4-morpholino-2,5-diethoxy, 4- 231 morpholino-2,5-dibutoxy, 4-(4'-tolylmercapto)-2,5 dibutoxy, 4-( 4 1 -tolylmercapto)-2,5-diethoxy, 4-(4' methoxybenzoylamino)-2,5-dibutoxy, 4-diphenylamino, etc. When any of these diazosulfonate compounds is 5 used, the diazosulfonate compound is preferably activated by light irradiation before printing. The diazoamino compound usable in the present invention is a compound obtained by coupling a diazo group with dicyandiamide, sarcosine, methyltaurine, N 10 ethylanthranilic acid-5-sulfonic acid, monoethanol amine, diethanolamine, guanidine or the like. The quinonediazide used in the present invention is considered as an internal-salt type diazonium salt from the viewpoint of structure and is, 15 for example, o-quinonediazide or o-naphthoquinone diazide. The quinonediazide includes salts, esters and amide compounds of 1,2-quinonediazide-4-sulfonic acid, 1,2-naphthoquinonediazide-5-sulfonic acid, 1,2 naphthoquinonediazide-4-sulfonic acid, etc. Specific 20 examples of the quinonediazide used in the present invention are sodium 1,2-quinonediazide-4-sulfonate, sodium 1,2-naphthoquinonediazide-5-sulfonate, sodium 1,2-naphthoquinonediazide-4-sulfonate, p-cumylphenyl 1,2-naphthoquinonediazide-5-sulfonate, p-cumylphenyl 25 1,2-naphthoquinonediazide-4-sulfonate, methyl 1,2 naphthoquinonediazide-5-sulfonate, ethyl 1,2 naphthoquinonediazide-5-sulfonate, 1,2-naphthoquinone diazide-5-sulfonic acid dimethylamide, esters of 1,2- 232 naphthoquinonediazide-5-sulfonic acid and a novolak resin, etc. In addition, these light-decomposable diazo compounds may be used singly or in combination. The coupler used in the present invention is 5 one that reacts with the diazo compound to form a pigment. For example, typical couplers capable of forming a yellow pigment are compounds which have a methylene group activated by a carbonyl group adjacent thereto and are represented by the general formula 10 RCOCH 2 CO-R' wherein R is an alkyl group or an allyl group, and R' is an aromatic amine. Magenta couplers are, for example, 1) cyanoacetyl derivatives of cyclic compounds, or 2) heterocyclic compounds having active methylene or any other coupling portion on the 15 heterocyclic ring. The magenta couplers include, for example, pyrazolone compounds and indazolone compounds. Cyan couplers include, for example, phenols and naphthols. Specific examples of the coupler used in the 20 present invention are 4-(p-toluenesulfonylamino)-co benzoylacetanilide, a-benzoyl-o-methoxyacetanilide, 2 cyanoacetyl-coumarone, 1-(2,4,6-trichlorophenyl)-3-p nitroamino-2-pyrazolon-5-one, resorcin, phloroglucin, 2,3-dihydroxynaphthalene, 2,6-dibromo-1,5-dihydroxy 25 naphthalene, N-(o-acetamidophenethyl)-1-hydroxy-2 napthoamide, etc. In addition, these couplers may be used singly or in combination. For smoother progress of the coupling 233 reaction of the diazo compound with the coupler under a basic atmosphere, a basic material is preferably incorporated into the heat-sensitive color-producing layer. As the basic material, a slightly water-soluble 5 or water-insoluble basic material or a material capable of producing an alkali on heating is used. The basic material includes, for example, nitrogen-containing compounds such as inorganic and organic ammonium salts, organic amines, amides, urea and thiourea and their 10 derivatives, thiazoles, pyrroles, pyrimidines, piperazines, guanidines, imidazoles, imidazolines, triazoles, morpholines, piperidines, amidines, formamidines, pyridines, etc. Specific examples of these compounds are 15 tricyclohexylamine, tribenzylamine, octadodecylbenzyl amine, stearylamine, allylurea, thiourea, methyl thiourea, allylthiourea, ethylenethiourea, 2-benzyl imidazole, 4 -phenylimidazole, 2-phenyl-4-methyl imidazole, 2 -undecylimidazoline, 2,4,5-trifuryl-2 20 imidazoline, 1, 2 -diphenyl-4,4-dimethyl-2-imidazoline, 2 -phenyl-2-imidazoline, 1,2, 3 -triphenylguanidine, 1,2 dicyclohexylguanidine, 1,2, 3 -tricyclohexylguanidine, guanidine trichloroacetate, N,N'-dibenzylpiperazine, 4,4'-dithiomorpholine, morpholinium trichloroacetate, 25 2 -aminobenzothiazole, 2 -benzoylhydrazinobenzothiazole, etc. These basic materials may be used singly or in combination. In the present invention, the storage 234 stability can be improved by adding a weakly acidic material such as citric acid, tartaric acid, oxalic acid, boric acid, phosphoric acid, pyrophosphoric acid or the like to the heat-sensitive color-producing layer 5 formed of a combination of the diazo compound and the coupler. Needless to say, the color-producing components used in the present invention can be used in a solid dispersion state attained by dispersing the 10 components in an aqueous solution of a water-soluble polymer, followed by coating and drying, as in a conventional method adopted in heat-sensitive recording materials. It is also possible to improve the green stability by encapsulating a color former to form 15 microcapsules and preventing the contact of the color former with a developer at ordinary temperatures by utilizing the isolating effect of the capsule walls, as described in JP-A-59-190886, JP-A-60-49991, JP-A-61 169281, etc. The microcapsules are characterized in 20 that they enable the color former and the developer to come into contact with each other only during heating at a certain temperature or higher. The temperature at the starting of the contact of the color former with the developer can be controlled by properly choosing a 25 material for the capsule wall, a core material for the capsule, additives, etc. As a material for the walls of the micro capsules in the present invention, there are mentioned 235 conventional materials for microcapsule wall, such as polyurethanes, polyureas, polyesters, polycarbonates, urea-formaldehyde resins, melamine resins, poly styrenes, styrene-methacrylate copolymers, gelatin, 5 poly(vinylpyrrolidone)s, poly(vinyl alcohol)s, etc. These polymers may be used singly or in combination. In the present invention, as the adhesive contained in the heat-sensitive color-producing layer, either water-soluble resins or water-dispersible resins 10 may be used. However, when any of these resins is mixed with dispersions of the above-mentioned color developable dye and developer, respectively, the resulting mixture should be free from coloration, aggregation and a high viscosity. In addition, a 15 coating film formed as heat-sensitive recording layer should be tough and should not have desensitizing effect. The content of the adhesive in the heat sensitive color-producing layer is preferably 8 to 20% based on the amount (in terms of solids) of the heat 20 sensitive color-producing layer. A content of less than 8% is disadvantageous in that the strength of the coating film is low. A content of more than 20% involves a problem of sensitivity decrease. In order to improve the water resistance of the heat-sensitive 25 color-producing layer, a crosslinking agent for curing the resin can be used. In the multicolor heat-sensitive recording material of the present invention, forming an inter- 236 mediate layer between heat-sensitive recording layers is effective in improving the thermal partitionment. The intermediate layer comprises as its main constituent the same resin as the water-soluble or 5 water-dispersible resin used as the adhesive in the heat-sensitive recording layers, and may further comprises pigments, crosslinking agents, etc. The coating amount of the intermediate layer is preferably 1.0 to 5.0 g/m 2 . When the coating amount is less than 10 1.0 g/m 2 , no sufficient preventive effect on diffusion between the recording layers can be obtained, resulting in a deteriorated quality of image. When the coating amount is more than 5.0 g/m 2 , the sensitivity is disadvantageously decreased. 15 As an especially preferable form of the multicolor heat-sensitive recording material of the present invention, there can be mentioned a multicolor heat-sensitive recording material in which two heat sensitive recording layers which have different color 20 development temperatures, respectively, and undergo color development in different color tones, respec tively, are laminated on one side of a substrate, and of these recording layers, the upper heat-sensitive recording layer contains either an agent used both as 25 developer and tone reducer, or a reversible developer, and the lower heat-sensitive recording layer contains the urea-urethane compound developer. Of these, the agent used both as developer 237 and tone reducer in the upper heat-sensitive recording layer is an amphoteric compound having an acidic group having a color-developing function and a basic group having an achromatizing function, which performs the 5 color-developing function on heating at a low tempera ture and performs the achromatizing function on heating at a high temperature. A typical example of the acidic group is phenolic hydroxyl group or carboxyl group. A typical example of the basic group is amino group. 10 Although the amphoteric compound may have the basic group as a functional group, it is preferably has the basic group as a portion of a salt compound, as in a complex of a phenolcarboxylic acid compound and an amine compound. Specific examples of such an agent 15 used -both as developer and tone reducer are as follows. The phenolcarboxylic acid compound that constitutes the agent used both as developer and tone reducer includes 2-hydroxybenzoic acid, 3-hydroxybenzoic acid, 4 hydroxybenzoic acid, 3,4-dihydroxybenzoic acid, 3,5 20 dihydroxybenzoic acid, 2,3-dihydroxybenzoic acid, 2,4 dihydroxybenzoic acid, 2,5-dihydroxybenzoic acid, 2,6 dihydroxybenzoic acid, gallic acid, bis(4-hydroxy phenyl)acetic acid, 3,3-bis(4-hydroxyphenyl)propionic acid, etc. 25 The amine compound that forms the salt or complex salt together with the phenolcarboxylic acid compound includes octylamine, nonylamine, decylamine, laurylamine, tetradecylamine, heptadecylamine, 238 stearylamine, behenylamine, 3 -methoxypropylamine, hexamethylenediamine, etc. The reversible developer is, for example, a phenolic compound or a phosphonic acid compound, which 5 has an aliphatic hydrocarbon group of 8 or more carbon atoms. Specific examples of such a reversible developer are those mentioned below. The reversible developer is not limited to those mentioned below, and any reversible developer may be used so long as it 10 performs a color-developing function on heating at a low temperature and performs an achromatizing function on heating at a high temperature. The reversible developer includes 4 (octadecylthio)phenol, 4-(dococylthio)phenol, 4 15 (octadecyloxy)phenol, 4-(dococyloxy)phenol,
N
octadecyl-4-hydroxybenzamide, 4'-hydroxydocosane anilide, N-(4-hydroxyphenyl)-N'-n-octadecylurea, docosylphosphonic acid, etc. When recording is conducted with a thermal printer or the like by using 20 the multicolor heat-sensitive recording material of the present invention, printing by heating at a low temperature causes color development only in the low temperature color-producing layer, and printing by heating at a high temperature causes achromatization in 25 the low-temperature color-producing layer in a print portion and causes color development only in the high temperature color-producing layer. Employment of the urea-urethane compound 239 makes it possible to obtain an article for laser marking which is sufficient in coloring density and gives such a very stable printed developed color image that the image is hardly discolored or faded even by 5 fats and oil, chemicals, fingerprints, etc. Therefore, the employment is especially advantageous from the viewpoint of long-term preservation of records. The heat-sensitive recording layer of the article for laser marking of the present invention 10 preferably contains a recording sensitivity improving agent. As the recording sensitivity improving agent usable therein, compounds capable of absorbing laser beams used for irradiation are used. Specific examples 15 thereof are various inorganic compounds such as aluminum hydroxide, wollastonite, bentonite, micas (e.g. muscovite and phlogopite), calcium silicate, talc, kaolin, clay, and silicate minerals (e.g. foyaite, hornblende and albite). Aluminum hydroxide, 20 muscovite, wollastonite and kaolin are especially preferable. These inorganic compounds may be used singly or as a mixture thereof. The proportions of the colorless or light colored dye precursor and recording sensitivity 25 improving agent used in the heat-sensitive recording layer in the present invention are not particularly limited and may be properly chosen depending on the kinds of the dye precursor and recording sensitivity 240 improving agent used. Usually, the recording sensi tivity improving agent can be used in a proportion of 10 to 5,000 parts by weight, preferably 100 to 2,000 parts by weight, per 100 parts by weight of the color 5 former. The contents of the dye precursor, the urea urethane compound developer and the recording sensi tivity improving agent in the heat-sensitive recording layer can be adjusted as follows: based on the total 10 weight (in terms of solids) of said layer, the content of the dye precursor ranges from 5 to 30 wt%, prefer ably from 10 to 25 wt%, the content of the urea urethane compound developer ranges from 10 to 60 wt%, preferably from 20 to 50 wt%, and the content of the 15 recording sensitivity improving agent ranges from 5 to 40 wt%, preferably from 10 to 30 wt%. The incorporation of also an acidic developer into the heat-sensitive recording layer of the article for laser marking of the present invention improves the 20 sensitivity and enables the article for laser marking to produce a brilliant color. As the acidic developer, the above-exemplified conventional electron-accepting materials are used. For further improving the sensitivity of the 25 article for laser marking of the present invention, a heat-meltable material can be incorporated into the heat-sensitive recording layer. The heat-meltable material is preferably one which has a melting point of 241 600C to 180*C, in particular, 800C to 140*C. The color-producing marking composition of the present invention can be obtained by using the above-mentioned colorless or light-colored dye 5 precursor, urea-urethane compound developer, recording sensitivity improving agent and aqueous binder and water as essential constituents, and mixing various assistants therewith if necessary. The water used in the color-producing marking 10 composition has a pH in a range of 5 to 12, preferably 6 to 9. When the pH is lower than 5, fog is caused. When the pH is higher than 12, there are likely to be undesirable influences such as loss of the color developing capability of the urea-urethane compound 15 developer. The water may be used in admixture with a water-soluble organic solvent such as methanol, ethanol or the like. In addition to the essential constituents described above, various assistants may, if necessary, 20 be incorporated into the color-producing marking composition used in the present invention, in order to, for example, facilitate the application of the composi tion on a substrate. The various assistants include, for example, dispersing agents (e.g. sodium dioctyl 25 sulfosuccinate, sodium dodecylbenzenesulfonate, lauryl alcohol sulfuric acid ester sodium salt, and fatty acid metal salts), opacifying agents (e.g. titanium oxide), defoaming agents, viscosity modifiers, fluorescent 242 dyes, and coloring agents. A substrate on which the color-producing marking composition of the present invention is printed (applied) is not particularly limited so long as it 5 requires marking. As the substrate, there are mentioned, for example, the predetermined portions of food containers, packaging materials, electronic parts and the like, and articles (e.g. substrates for label) to be attached thereto. As the substrates for label, 10 papers (e.g. paper and synthetic paper), synthetic resin films, plastics, metallized paper and synthetic paper, metallized films, metals, wood, etc. are properly used depending on their purpose. The color-producing marking composition is 15 prepared, for example, as follows. The binder is dissolved or dispersed in water or a solvent composed mainly of water. Among the color former, the developer, the recording sensitivity improving agent and the like, components that should be dispersed in 20 water or a solvent composed mainly of water are treated together or individually in water or an aqueous solvent, which contains a dispersing agent such as a poly(vinyl alcohol), by using a dispersing machine such as a ball mill, attritor, sand grinder or the like, 25 whereby one or more dispersions are prepared. The average particle size of each component after the dispersing operation is usually about 2 pt or less, preferably about 1 p or less. Then, the binder and the 243 dispersion(s) are mixed to obtain the color-producing marking composition of the present invention. The solid content of said color-producing marking composi tion is 20 to 70 wt%, preferably about 30 to about 65 5 wt%. The color-producing marking composition may be applied directly on the substrate, or it may be applied on the substrate that has been previously subjected to surface treatment, undercoating or the 10 like. The application can be carried out by using a suitable coater such as a roll coater, gravure coater, micro-gravure coater, knife coater, spray coater or the like. The thickness of the coating film (the heat sensitive recording layer) obtained by the application 15 and drying can be usually adjusted to 1 to 4 pt. When the thickness is less than 1 ij, color development by laser irradiation is not sufficient and moreover, the coating film tends to be peeled off. On the other hand, when the thickness is more than 4 pt, the drying 20 characteristics and the label attachability tend to be deteriorated. The drying is varied depending on coat ing conditions such as the speed of line and may be conducted either at room temperature, or by heating under conditions which do not cause color development 25 in the heat-sensitive recording layer. The protective layer of the article for laser marking of the present invention is formed by applying a transparent clear coating liquid on the heat- 244 sensitive recording layer. The clear coating liquid is an aqueous composition consisting of an aqueous binder, water and the like. As the aqueous binder used in the clear 5 coating liquid for the protective layer in the present invention, there are mentioned those obtained by using as a base a per se known water-soluble or water dispersible resin used in a coating material or ink. Such a resin has a hydrophilic group (e.g. carboxyl 10 group or amino group) optionally introduced thereinto for impartment of the water-solubility or water dispersibility. As said resin for the aqueous binder, a resin having a glass transition temperature in a range of 20 - 80*C, preferably 35 - 70'C is used. When 15 the glass transition temperature is lower than 20 0 C, the scuff resistance, chemical resistance, water resistance and the like of the protective layer are deteriorated. On the other hand, when the glass transition temperature is higher than 80 0 C, the protec 20 tive layer is brittle, is poor in flexibility and the like, and is easily cracked. Therefore, both of such glass transition temperatures are not desirable. If necessary, leveling agents, slip-properties-imparting agents, defoaming agents and the like may be incorpo 25 rated into said clear coating liquid in addition to the components described above. As the aqueous binder used in the clear coating liquid, an acrylic resin can be obtained by 245 using an alkyl (number of carbon atoms: 1 to 24) ester of acrylic acid or methacrylic acid as a main component in combination with any of, for example, unsaturated carboxylic acids such as acrylic acid, methacrylic 5 acid, maleic acid, etc.; hydroxy-containing unsaturated monomers such as hydroxyethyl acrylate, hydroxypropyl methacrylate, etc.; amino-containing unsaturated monomers such as acrylamide, methacrylamide, etc.; and other unsaturated monomers such as styrene, 10 acrylonitrile, vinyl acetate, vinyl chloride, etc., and copolymerizing the alkyl ester with such a comonomer. A polyester resin can be obtained by the ester reaction of a polybasic acid (including acid anhydrides) having two or more carboxyl groups in the molecule with a 15 polyhydric alcohol having two or more hydroxyl groups in the molecule. The glass transition point of such an aqueous binder can be adjusted to any temperature by properly choosing the kinds, combination and propor tions of components that constitute said binder. 20 Said clear coating liquid is prepared by dissolving or dispersing the above-mentioned aqueous binder in suitable water, and if necessary, is incorporated with leveling agents, slip-properties imparting agents, defoaming agents and the like. The 25 solid content of said clear coating liquid ranges preferably from 20 to 70 wt%, in particular, from 30 to 60 wt%. Said clear coating liquid can be printed 246 (applied) on the surface of a dried coating film formed as the heat-sensitive recording layer. A method for the printing (application) is not particularly limited. The application can be carried out by means of a roll 5 coater, gravure coater, micro-gravure coater, spray coater or the like. The thickness of the coating film thus formed can be usually adjusted to 3 to 10 p. When the thick ness is less than 3 p, the protection of the heat 10 sensitive recording layer afforded by said clear coating is not sufficient and the chemical resistance, rub resistance and the like are deteriorated. On the other hand, when the thickness is more than 10 p, the drying characteristics and physical performance of the 15 coating film tend to be deteriorated. Drying of said clear coating liquid is varied depending on coating conditions such as the speed of line and may be conducted either at room temperature, or by heating under conditions which do not cause color development 20 in the heat-sensitive recording layer. When the thus formed heat-sensitive recording layer of the article for marking is irradiated with laser beams, the irradiated portion is heated, so that the urea-urethane compound developer and the dye 25 precursor react with each other to develop a color, resulting in marking. Although the amount of energy of laser beams used for the irradiation is not particu larly limited, it is preferably 1.4 J (joule)/cm 2 or 247 less when the possibility of fracture of the coating film is taken into consideration. On the other hand, although the lower limit of the amount of energy required for color development is unknown because there 5 is no apparatus capable of producing low energy, sufficient color development takes place even at an amount of energy of 0.4 J/cm 2 . Therefore, the suitable amount of energy for color development by the irradia tion ranges from 0.4 to 1.4 j/cm 2 , in particular, from 10 0.45 to 1.2 J/cm 2 . As a laser used for the irradiation, a pulsed laser or a scanning laser is suitable. As to the kind of the laser, any of, for example, gas lasers, excimer lasers and semiconductor lasers may be used. Specific examples of the laser are carbon dioxide 15 lasers, mixed gas lasers, YAG lasers, ruby lasers, etc. As a method for irradiating a portion of a desirable form with laser beams, there are mentioned a method of irradiating the coating film with laser beams through a metal mask to irradiate the coating film with 20 laser beams in conformity with the form of the opening of the metal mask; and a method of inputting a desirable form to a computer and irradiating the coating film with laser beams in accordance with the desirable form in a manner of so-called drawing with a 25 single stroke. When the heat-sensitive recording layer is irradiated with laser beams, the irradiated portion is increased in temperature to undergo color develop ment caused by melting and mixing of the color- 248 producing components in the heat-sensitive recording layer, resulting in the appearance of letters or a figure, which has a clear desirable form. This color change by the irradiation can be carried out in a 5 moment because the energy density of laser beams is high. A label as the article for laser marking of the present invention can be produced by forming a heat-sensitive recording layer and a protective layer 10 by the above-mentioned methods on a substrate for label properly selected depending on its purpose from papers (e.g. paper and synthetic paper), synthetic resin films, plastics, metallized paper and synthetic paper, metallized films, metals, etc. Although the label thus 15 obtained can be used in all the fields of conventional labels, it is preferably used in the fields of, in particular, food, medicine, toiletries, publications, and electric and electronic parts, etc. A packaging material as the article for laser 20 marking of the present invention is produced by forming a heat-sensitive recording layer and a protective layer by the above-mentioned methods on any of various conventional packaging materials such as boxes, packing paper and packages, which are obtained by the use of a 25 substrate properly selected depending on its purpose from papers (e.g. paper and synthetic paper), synthetic resin films, plastics, metallized paper and synthetic paper, metallized films, metals, glass, wood, etc.
249 Although said packaging material can be used in all the fields of conventional packaging materials, it is preferably used in the fields of, in particular, food, medicine, toiletries, publications, and electric and 5 electronic parts, etc. A container as the article for laser marking of the present invention is produced by forming a heat sensitive recording layer and a protective layer on a substrate such as glass, plastic, metal or the like by 10 the above-mentioned methods. This food container can be used in all the fields of conventional food containers, such as the fields of bottles for liquors and refreshing drinks, retort-food containers, instant food containers, cosmetics containers, medicine 15 container, toiletry products, etc. When the color-producing composition of the present invention is used in a pressure-sensitive recording material, the recording material can have, for example, the forms disclosed in U.S. Patent Nos. 20 2505470, 2712507, 2730456, 2730457 and 3418250, etc. That is, various forms such as the following forms can be employed: a pressure-sensitive recording paper obtained by dissolving the dye precursor or a mixture of the dye precursors in a solvent consisting of one of 25 or a mixture of two or more of alkylated naphthalenes, alkylated diphenyls, alkylated diphenylmethanes, alkylated diarylethanes, synthetic oils (e.g. chlorinated paraffin), vegetable oils, animal oils, 250 mineral oils, etc., dispersing the resulting solution in a binder or incorporating the solution into micro capsules, applying the dispersion on a substrate or applying the microcapsules on a substrate together with 5 a binder, and placing the upper paper thus obtained and under paper coated with a dispersion of the urea urethane compound (and an amino compound and/or a developer, etc.), one upon the other so that their coated surfaces face each other; a pressure-sensitive 10 recording paper obtained by holding, between the above mentioned upper paper and under paper, an intermediate paper coated with a dispersion of the urea-urethane compound on one side and the dye precursor on the other side; a self-type pressure-sensitive recording paper 15 obtained by applying the above-mentioned dispersion of the urea-urethane compound (and an amino compound and/or a developer) and the above-mentioned dispersion containing the dye precursor, on the same surface of a substrate as a mixture or in a multilayer form; and a 20 self-type pressure-sensitive recording paper obtained by making each of the dye precursor and the urea urethane compound (and an amino compound and/or a developer) into microcapsules, and applying a mixture of the microcapsules of the two kinds on the same 25 surface of a substrate. As a process for producing microcapsules, there can be adopted, for example, the coacervation processes disclosed in U.S. Patent Nos. 2800457 and 251 2800458, the interfacial polymerization processes disclosed in JP-B-38-19574, JP-B-42-446, JP-B-42-771, etc., the in-situ processes disclosed in JP-B-36-9168, JP-B-51-9079, etc., the melt dispersion cooling 5 processes disclosed in Brit. Patent Nos. 952807 and 96 5074, etc., and the spray drying processes disclosed in U.S. Patent No. 311140, Brit. Patent No. 930422, etc. The color-producing composition of the present invention corresponds to the combination of a 10 dye precursor and a developer described in each of the above references and the like. For forming a pressure-sensitive recording layer, each component such as the urea-urethane compound may be used in the form of a solution or 15 dispersion in a solvent. In the case of a color producing system further comprising an amino compound and/or a developer, each component may be used in the form of a solution or dispersion in a solvent, or a combination of the urea-urethane compound, the amino 20 compound and optionally the developer may be used in the form of a solution or dispersion in a solvent. In the above-mentioned interfacial polymer ization processes adopted for forming microcapsules, a film is formed on an interface by using two kinds of 25 monomers, i.e., an oil monomer and a water-soluble monomer. There are known, for example, a process in which a polybasic acid chloride is used as an oil phase and a polyvalent amine as an aqueous phase, and a 252 polyamide film is formed on the interface; a process in which a polybasic acid chloride is used as an oil phase and a polyhydric hydroxy compound as an aqueous phase, and a polyester film is formed on the interface; a 5 process in which a polyvalent isocyanate is used as an oil phase and a polyhydric alcohol or a polyhydric phenol as an aqueous phase, and a polyurethane film is formed on the interface; and a process in which a polyvalent isocyanate is used as an oil phase and a 10 polyvalent amine as an aqueous phase, and a polyurea film is formed on the interface. Thus, when the interfacial polymerization process is adopted for producing microcapsules, an isocyanate compound is used in some cases as a reactive monomer for forming a film. 15 In this case, said isocyanate compound is consumed in forming a film for microcapsules and is not directly concerned with a developed color image, and it is absolutely necessary to use a water-soluble monomer together with the isocyanate compound. In these 20 points, its employment is distinguished from the employment of the isocyanate compound according to the present invention. Dispersions of compounds which are not made into microcapsules are prepared by finely grinding one 25 or more compounds as each component in an aqueous solution containing a compound having dispersing capability, such as a water-soluble polymer, a surfactant or the like. The urea-urethane compound may 253 be dispersed together with an amino compound and an acidic developer. As the substrate used in the pressure sensitive recording material, paper is mainly used, 5 though any of various woven fabrics, nonwoven fabrics, synthetic resin films, laminated papers, synthetic papers, metal foils, and composite sheets obtained by combining two or more of them may be used besides paper, depending on their purpose. 10 As a binder, conventional various binders can be used. The binder includes, for example, water soluble binders such as starches, hydroxyethyl cellulose, methyl cellulose, carboxymethyl cellulose, gelatin, casein, poly(vinyl alcohol)s, modified 15 poly(vinyl alcohol)s, sodium poly(acrylate)s, acrylamide-acrylic ester copolymers, acrylamide-acrylic ester-methacrylic acid terpolymers, alkali salts of styrene-maleic anhydride copolymers, alkali salts of ethylene-maleic anhydride copolymers, etc.; and latex 20 type water-insoluble binders of styrene-butadiene copolymers, acrylonitrile-butadiene copolymers, methyl acrylate-butadiene copolymers, etc. In the recording material of the present invention, the recording layer may contain a hindered 25 phenol compound or an ultraviolet absorber. The hindered phenol compound or ultraviolet absorber includes, for example, 1,1,3-tris(3'-cyclohexyl-4' hydroxyphenyl)butane, 1,1,3-tris(2-methyl-4-hydroxy-5- 254 tert-butylpheny)butane, 4,4'-thiobis(3-methyl-6-tert butylphenol), 1,3,5-trimethyl- 2,4,6-tris(3,5-di-tert butyl-4-hydroxybenzyl)benzene, 2,2'-dihydroxy-4,4' dimethoxybenzophenone, p-octylphenyl salicylate, 2-(2' 5 hydroxy-5'-methylpheny)benzotriazole, ethyl-2-cyano 3,3'-diphenyl acrylate and tetra(2,2,6,6-tetramethyl-4 piperidyl)-1,2,3,4-butanetetracarbonate. A method for forming the color-producing layer is not particularly limited. The color-producing 10 layer is formed, for example, by applying a coating liquid for the color-producing layer on a substrate by a suitable coating method such as free-fall curtain coating, air-knife coating, Bariber blade coating, Pure blade coating, short-dwell coating or the like, and 15 drying the thus treated substrate. The coating amount of the coating liquid for the color-producing layer is not particularly limited and is usually controlled in a range of 1 to 15 g/m 2 , preferably about 3 to about 10 g/m 2 , in terms of dry weight. 20 The thermal response can be improved by forming an intermediate layer between the heat sensitive recording layer and the substrate. In the case of conventional heat-sensitive recording materials, a technique for improving the color 25 development sensitivity, for example, by co-using a heat-meltable material in a color-producing layer has been employed. The improvement of the sensitivity by such a method is disadvantageous in that fog tends to 255 be caused by heat or friction. It facilitates the occurrence of fog particularly in heat-sensitive recording materials obtained by using the urea-urethane compound developer excellent in color development 5 sensitivity. In the case of conventional heat sensitive recording materials without print preserv ability, even if fog is caused, it disappears like a print, so that, in particular, fog in the case of using the recording material after long-term storage is 10 seldom taken into account. However, in the case of heat-sensitive recording materials obtained by using the urea-urethane compound developer especially excellent in long-term print preservability, the following problem characteristic of them is caused in 15 some cases: when fog is once caused, it is preserved and hence it is accumulated each time the recording material is stored and then used, so that the recording material surface becomes dirty when the recording material is used after long-term storage. In such a 20 case, by forming the intermediate layer, a practical color development sensitivity can be attained without using a heat-meltable material or by using only a small amount of a heat-meltable material, and a heat sensitive recording material can be obtained which is 25 so excellent in resistance to fog caused by heat or friction that the fog is hardly accumulated even if the recording material is used after long-term storage. The intermediate layer is composed mainly of 256 an organic or inorganic pigment, hollow particles and an aqueous binder such as a water-soluble polymer or a latex. As the organic or inorganic pigment and the aqueous binder, the same organic or inorganic pigment 5 and aqueous binder as used in the heat-sensitive recording layer can be used. A method for forming the intermediate layer is not particularly limited. As this method, the same method as the method for forming the heat-sensitive recording layer can be adopted. The 10 dry spread for forming the intermediate layer ranges preferably from 2.0 to 15.0 g/m 2 . In this case, the surface pH of the intermediate layer formed on the substrate is preferably 3 to 9, more preferably 5 to 9, most preferably 6 to 8. 15 In addition, in the present invention, the rub resistance of the resulting recording paper can be improved by forming a protective layer composed mainly of a water-soluble polymer, on the heat-sensitive recording layer if necessary. When the urea-urethane 20 compound developer of the present invention is used which is excellent in color development sensitivity and resistance of print to long-term storage, a trace of rubbing tends to be left because of the high sensi tivity. On the other hand, the trace of rubbing once 25 left is preserved for an indefinite time and hence traces of rubbing are accumulated each time the record ing material is stored and then used. Therefore, the paper surface becomes dirty in some cases when the 257 recording paper is used after long-term storage. In such a case, by forming the protective layer, the accumulation of traces of rubbing can be made difficult even if the recording paper is used after long-term 5 storage. Specific examples of the water-soluble polymer contained in the protective layer are the water-soluble polymer binders mentioned in relation to the above-mentioned heat-sensitive recording layer. The water-soluble polymer can be used together with a 10 conventional waterproofing agent capable of waterproof ing the water-soluble polymer. Specific examples of the waterproofing agent are formaldehyde, glyoxal, chrome alum, melamine, melamine-formaldehyde resins, polyamide resins, polyamide-epichlorohydrin resins, 15 etc. Furthermore, pigments, metal soaps, waxes, crosslinking agents, etc. are incorporated into the protective layer for the purpose of, for example, improving the matching with a thermal head during 20 printing and improving the water resistance of the protective layer. The pigments include zinc oxide, calcium carbonate, barium sulfate, titanium oxide, lithopone, talc, pagodite, kaolin, aluminum hydroxide, silica, 25 amorphous silica, etc. The amount of the pigments added is 0.5 to 4 times, preferably 0.8 to 3.5 times, the total weight of the polymers. When the amount is below the lower limit of the above range, the pigments 258 are not effective in improving the matching with a thermal head. When the amount is above the upper limit, the sensitivity of the heat-sensitive recording material is remarkably decreased, so that the 5 commercial value of the recording material is impaired. The metal soaps include, for example, emulsions of higher fatty acid metal salts such as zinc stearate, calcium stearate, aluminum stearate, etc. The metal soaps are added in a proportion of 0.5 to 20 10 wt%, preferably 1 to 10 wt%, based on the total weight of the protective layer. The waxes include, for example, emulsions of paraffin wax, microcrystalline wax, carnauba wax, methylolstearoamide, polyethylene wax, etc. The waxes are added in a proportion of 1 to 15 20 wt%, preferably 1 to 10 wt%, based on the total weight of the protective layer. In forming the protective layer on the heat sensitive recording layer, a surfactant is added to a coating liquid for forming the protective layer, in 20 order to obtain a uniform coating layer. The surfactant includes alkali metal salts of sulfosuccinic acids, fluorine-containing surfactants, etc. Specific examples of the surfactant are sodium salts or ammonium salts of di-(2-ethylhexyl)sulfosuccinic acid, di-(n 25 hexyl)sulfosuccinic acid, etc. In general, any surfactant is effective so long as it is anionic. Conventional auxiliary additives such as fillers, heat meltable materials (lubricants), surfactants, 259 fluorescent dyes, etc. may also be incorporated into the protective layer. Specific examples of the fillers, heat-meltable materials and fluorescent dyes are those mentioned in relation to the above-mentioned 5 heat-sensitive recording layer. The dry spread of the protective layer is preferably about 0.5 to about 10 g/m 2 , in particular, about 1 to about 5 g/m 2 . When a reverse-side layer (a back coating layer) is, if necessary, formed on the side reverse to 10 the recording layer of the recording material produced by the process of the present invention, curling of the resulting recording paper can be made difficult. Particularly in the case of the urea-urethane compound developer of the present invention, the formation of 15 the reverse-side layer is effective for the following reason: said developer is superior to other developers in dispersibility, gives a dispersion with a small particle size easily, and has a high sensitivity, but when a coating liquid prepared by mixing said developer 20 with other necessary components is applied on a substrate, the cohesive force of a binder is increased at the time of drying because of the small particle size of the developer, so that the recording layer is eaily shrunk, resulting in easy curling. As the 25 components of the coating liquid for the reverse-side layer and a coating method for the coating liquid, the same components and method as in the case of the protective recording layer may be employed. The dry 260 spread of the coating liquid ranges preferably from 0.2 to 10.0 g/m 2 . The present invention is explained in further detail with the following examples. 5 The analyses of materials and the evaluation of physical properties were carried out by the follow ing methods. <IR spectrum> Measured by diffuse reflectance spectroscopy 10 by the use of FTIR-8100M manufactured by Shimadzu Corp. <Mass spectrum> Measured by using JMS-HX100 manufactured by JEOL LTD., nitrobenzyl alcohol as a matrix, and xenon as a primary gas. 15 <Color development sensitivity of thermal paper> Coloring density at an applied voltage of 24 V and a pulse width of 1.5 msec was measured with an optical densitometer by using a printing tester manufactured by Ohkura Denki K.K., and a thermal head 20 KJT-256-8MG manufactured by Kyocera Co., Ltd. <Plasticizer resistance> A heat-sensitive recording material was held between vinyl chloride wrap films or in a vinyl chloride file, and a load of 300 g/cm 2 was applied 25 thereto from above. After standing at 40 0 C for 24 hours, the 'coloring density of the printed portion and the non-printed portion (the original recording material surface) was visually estimated. When there 261 was only a slight decrease in print density, the print preservability was rated as good. <Heat resistance> A heat-sensitive recording material was 5 allowed to stand at 60 0 C and 25% RH for 24 hours and the degree of fading of print was visually estimated. When the degree of fading is low, the print preservability was rated as good. In addition, a heat-sensitive recording 10 material was allowed to stand at 80 0 C and 25% RH for 24 hours and the degree of fading of print was visually estimated. When the degree of fading was low, the print preservability was rated as good. The coloring density of the original recording material surface was 15 also visually estimated. When the color development was slight, the preservability of original recording material surface was rated as good. <Coloring density of pressure-sensitive paper> Upper paper and under paper were placed one 20 upon the other so that their coated surfaces might face each other. A pressure was applied thereto from above to obtain a developed color image on the under paper. The color density of the developed color image was measured by means of a densitometer Macbeth RD917. 25 <Solvent resistance> Hand cream (Atrix, a trade name, mfd. by Kao Corp.) was thinly applied on the developed color image portion obtained in the coloring density estimation, 262 and after standing at ambient temperature for 7 days, the color density of print portion was visually estimated. When there was only a slight decrease in print density, the print preservability was rated as 5 good. Example 1 To 27.8 g of 2,4-toluene diisocyanate was added 111 g of toluene as a solvent, followed by adding dropwise thereto a solution of 7.4 g of aniline in 37 g 10 of toluene at room temperature over a period of 1 hour, and the reaction was carried out for another 1 hour. The white solid precipitated was recovered by filtra tion, washed with hexane and then dried overnight in a vacuum to obtain 20 g of white crystals. Subsequently, 15 5 g of the thus obtained compound was added to 50 mL of methanol, and the reaction was carried out at 60*C for 30 minutes, after which the excess methanol was removed by the use of an evaporator, and toluene was added to the residue to effect crystallization. The resulting 20 white crystals were recovered by filtration, washed with hexane and then dried overnight in a vacuum to obtain 5.4 g of white crystals. The melting point of these white crystals was 196'C. Analytical measurement of these white 25 crystals was as follows. Result of IR measurement: Characteristic peaks appeared at 1060 cm-', 263 1250 cm- 1 , 1600 cm-', 1650 cm-', 1670 cm- 1 , 1700 cm~ 1 and 3300 cm-1. The structural formula of the major component of this compound is presumed to be the structural 5 formula of the above-mentioned compound (S-1). Next, a dispersion was prepared by dispersing 2 g of this compound by grinding it together with 8 g of a 2.5 wt% aqueous solution of a poly(vinyl alcohol) (Gohseran L-3266, a trade name, mfd. by The Nippon 10 Synthetic Chemical Industry Co., Ltd.) in a paint shaker for 6 hours. The temperature of the dispersion immediately after the dispersing operation was 25*C. The diameter of dispersed particles of the compound was about 0.6 pm. 15 Another dispersion was prepared by dispersing 70 g of 3 -dibutylamino-6-methyl-7-anilinofluoran by grinding it together with 130 g of a 8 wt% poly(vinyl alcohol) aqueous solution in a sand grinder (mfd. by AIMEX CO., LTD.; vessel capacity 400 ml) at a number of 20 revolution of 2,000 rpm for 3 hours. Further another dispersion was prepared by dispersing 70 g of diphenyl sulfone by grinding it together with 130 g of a 5.4 wt% poly(vinyl alcohol) aqueous solution in a sand grinder (mfd. by AIMEX CO., 25 LTD.; vessel capacity 400 ml) at a number of revolution of 2,000 rpm for 3 hours. Still another dispersion was prepared by mixing 10 g of calcium carbonate with 30 g of water and 264 stirring the mixture by the use of a stirrer. A coating liquid was obtained by stirring and mixing the above-mentioned dispersions and other components in the following proportions (dry basis 5 proportions); the dispersion of the above-mentioned compound in terms of dry solids: 30 parts by weight, the 3-dibutylamino-6-methyl-7-anilinofluoran dispersion in terms of dry solids: 15 parts by weight, the diphenyl sulfone dispersion in terms of dry solids: 30 10 parts by weight, the calcium carbonate dispersion in terms of dry solids: 20 parts by weight, a zinc stearate dispersion (solid content: 16 wt%) in terms of dry solids: 10 parts by weight, and a 15 wt% poly(vinyl alcohol) in terms of dry solids: 7 parts by weight. 15 The coating liquid was applied on base paper with a basis weight of 50 g/m 2 by the use of a bar coater of rod number 10. After drying, supercalender ing was conducted to obtain a heat-sensitive recording material. The coating amount of the coating liquid was 20 4 g/m 2 in terms of dry weight. The result of evaluating the sensitivity of the heat-sensitive recording material obtained was so good that the optical density was 1.2. The result of estimating the degree of a thermal color change of the 25 original recording material surface (the heat resist ance) was so good that the color change was slight. The thermal fading of the print portion was desirably slight. These evaluation results are summarized in 265 Table 1. Example 2 To 17 g of 2,4-toluene diisocyanate was added 40 g of methyl ethyl ketone as a solvent, followed by 5 adding dropwise thereto 3.8 g of methanol, and the reaction was carried out with stirring at 60 0 C for 5 hours. Then, 9.9 g of 4,4'-diaminodiphenyl sulfone was added thereto, and the reaction was carried out with stirring at 60*C for 4 hours. After completion of the 10 reaction, the reaction solution was cooled to room temperature and poured into 800 g of acetonitrile, and the crystals precipitated were recovered by filtration, washed with hexane and then dried overnight in a vacuum to obtain 15 g of a compound as white crystals. 15 The melting point of the white crystals was 169 0 C, and their analytical measurements were as follows. Result of IR measurement: Characteristic peaks appeared at 1220 cm-1, 20 1550 cm~1, 1590 cm~', 1660 cm~1, 1740 cm~1 and 3300 cm~'. Result of mass spectrum measurement: [M+H]* was detected at m/z 661. The structural formula of the major component of this compound is presumed to be the structural 25 formula of the above-mentioned compound (S-13). Then, a heat-sensitive recording material was produced in the same manner as in Example 1 except for 266 using the compound obtained above, in place of the urea-urethane compound synthesized in Example 1, and was evaluated. The results obtained are summarized in Table 1. 5 Example 3 In 100 mL of ethyl acetate was dissolved 3.46 g of aniline, and the resulting solution was stirred at room temperature. A solution of 10 g of trimethylol propane adduct of toluene diisocyanate (Coronate L, a 10 trade name, mfd. by Nippon Polyurethane Industry Co., Ltd.; a 75% ethyl acetate solution) in 50 mL of ethyl acetate was added dropwise thereto over a period of 1 hour, and the reaction was carried out for another 30 minutes. The crystals formed were recovered by 15 filtration and dried overnight in a vacuum to obtain 5.1 g of a compound as white crystals. The melting point of the white crystals was 161*C, and their analytical measurement was as follows. Result of IR measurement: 20 Characteristic peaks appeared at 1070 cm~1, 1220 cm~1, 1550 cm-, 1600 cm-1, 1700 cm~1 and 3300 cm'. The structural formula of the major component of this compound is presumed to be the structural formula of the above-mentioned compound (S-33). 25 Then, a heat-sensitive recording material was produced in the same manner as in Example 1 except for using the compound obtained above, in place of the 267 urea-urethane compound synthesized in Example 1, and was evaluated. The results obtained are summarized in Table 1. Example 4 5 To 10.4 g of 2,4-toluene diisocyanate was added 20 g of methyl ethyl ketone as a solvent, followed by adding dropwise thereto a dilution of 3.7 g of 4,4'-diaminodiphenyl sulfone with 30 g of methyl ethyl ketone, and the reaction was carried out at 10 ambient temperature for 20 hours. After completion of the reaction, the methyl ethyl ketone was removed by concentration and then toluene was added to the residue, and the white solid precipitated was recovered by filtration, washed with hexane and then dried over 15 night in a vacuum to obtain 8.8 g of a compound as white crystals. Subsequently, 15 g of phenol and then a small amount of dibutyltin dilaurate were added to 4 g of the obtained compound, and the reaction was carried out at 50*C for 4 hours. After completion of 20 the reaction, toluene was added to the reaction solution and the crystals precipitated were recovered by filtration, washed with hexane and then dried overnight in a vacuum to obtain 5.2 g of a urea urethane compound as white crystals. 25 Then, 30 g of toluene was added as solvent to 10 g of 2,4-toluene diisocyanate, followed by adding thereto 30 g of phenol, and the reaction was carried 268 out at 1000C for 3 hours. After completion of the reaction, the toluene was removed by concentration and hexane was added to the residue. The white crystals precipitated were recovered by filtration, washed with 5 hexane and then dried overnight in a vacuum to obtain 15 g of a urethane compound as white crystals. The structural formula of the major component of this compound is presumed to be the structural formula of the compound (C-2) described hereinafter. 10 Next, 3 g of the above-mentioned urea urethane compound and 2 g of the urethane compound were mixed to obtain a urea-urethane composition. There after, 2 g of the urea-urethane composition was ground together with 8 g of a 2.5 wt% methyl cellulose aqueous 15 solution in a paint shaker for 45 minutes to be dispersed, whereby a dispersion was obtained. Then, a heat-sensitive recording material was produced in the same manner as in Example 1 except for using this dispersion of said composition in place of 20 the dispersion of the compound obtained in Example 1, and was evaluated. The results obtained are summarized in Table 1. Example 5 A heat-sensitive recording material was 25 produced in the same manner as in Example 4 except for using a urea-urethane composition obtained by mixing 4.5 g of the urea-urethane compound and 0.5 g of the 269 urethane compound which had been synthesized in Example 4, in place of the urea-urethane composition used in Example 4, and was evaluated. The results obtained are summarized in Table 1. 5 Example 6 A heat-sensitive recording material was produced in the same manner as in Example 4 except that in place of the urea-urethane composition used in Example 4, there was used 7.4 g of a urea-urethane 10 composition obtained as white crystals in the same manner as in Example 4 except for adding 2.2 g of diphenyl sulfone to the reaction system before the precipitation by the addition of toluene after the synthetic reaction of the urea-urethane compound, 15 stirring the resulting mixture, adding toluene to the mixture, recovering the crystals precipitated, by filtration, washing the crystals with hexane, and then drying the crystals overnight in a vacuum. The heat sensitive recording material was evaluated. The 20 results obtained are summarized in Table 1. Example 7 To 31.5 g of 2,4-toluene diisocyanate was added dropwise a solution of 21.5 g of 4,4'-diamino diphenyl sulfone in 60 mL of MEK at 70*C with stirring 25 at 300 to 500 rpm over a period of 4 hours, and the reaction was carried out for another 4 hours to obtain 270 a white viscous slurry reaction mixture. Then, the reaction mixture was cooled to 50*C, and 17.1 g of phenol was poured into the reaction mixture to be dissolved therein, after which 0.015 g of triethylamine 5 was added thereto as a catalyst, and the reaction was carried out for 4 hours to obtain a yellow, transparent and viscous reaction mixture. This reaction mixture was freed from the solvent and concentrated under reduced pressure to be solidified, after which the 10 resulting solid was ground and then dried overnight in a vacuum to obtain about 70 g of a urea-urethane composition as light-yellow powder. The melting point of the light-yellow powder was 160 - 180 0 C. In IR measurement of the powder, a 15 wide peak formed by overlapping of characteristic peaks due to urea group and urethane group, respectively, appeared at 1700 cm'. The content of the urea-urethane main consti tuent in the urea-urethane composition was 68% as 20 measured by liquid chromatography. Then, a heat-sensitive recording material was produced in the same manner as in Example 1 except for using the above-mentioned composition in place of the urea-urethane compound synthesized in Example 1, and 25 was evaluated. The results obtained are summarized in Table 1.
271 Example 8 To 158.5 g of 2,4-toluene diisocyanate was added 240 g of methyl ethyl ketone as a solvent, and 107.5 g of 4,4'-diaminodiphenyl sulfone was added 5 thereto in the form of powder at 300C with stirring at 400 rpm over a period of 8 hours. After 1 hour, 26 g of methyl ethyl ketone was added thereto and stirred for another 15 hours to obtain a white viscous slurry reaction mixture. Then, a solution of 89.5 g of phenol 10 in 15.8 g of methyl ethyl ketone was poured into the reaction mixture to be dissolved therein, after which 9.3 g of a 1 wt% solution of triethylamine in methyl ethyl ketone was added thereto as a catalyst over a period of 2 hours, and the reaction was continued for 1 15 hour. Thereafter, the reaction mixture was cooled to 20*C and continuously stirred for 3 hours to obtain a slurry containing slightly yellow crystals precipitated therein. The slurry was freed from the solvent and concentrated under reduced pressure to be solidified, 20 after which the resulting solid was ground and then dried overnight in a vacuum to obtain 355 g of a urea urethane composition as slightly yellow powder. The melting point of the slightly yellow powder was 130 - 170*C. In IR measurement of the 25 powder, a wide peak formed by overlapping of character istic peaks due to urea group and urethane group, respectively, appeared at 1700 cm'. The content of the urea-urethane main constituent in the urea-urethane 272 composition was 65% as measured by liquid chromato graphy. Then, a heat-sensitive recording material was produced in the same manner as in Example 1 except for 5 using the above-mentioned composition in place of the urea-urethane compound synthesized in Example 1, and was evaluated. The results obtained are summarized in Table 1. Example 9 10 To 27.8 g of 2,4-toluene diisocyanate was added 100 g of toluene as a solvent, followed by adding dropwise thereto a solution of 7.4 g of aniline in 37 g of toluene at room temperature over a period of 1 hour, and the reaction was carried out for another 1 hour. 15 The white solid precipitated was recovered by filtra tion, washed with hexane and then dried overnight in a vacuum to obtain 20 g of white crystals. Subsequently, 5 g of the thus obtained compound was added to 50 mL of methanol, and the reaction was carried out at 60*C for 20 30 minutes, after which the excess methanol was removed by the use of an evaporator, and the residue was dried overnight in a vacuum to obtain 5.4 g of a urea urethane composition as white crystals. The melting point of the white crystals was 196*C. In IR measure 25 ment of the crystals, characteristic peaks due to a urea-urethane compound appeared at 1670 cm-1 and 1700 cm-1. The content of the urea-urethane main constituent 273 in the urea-urethane composition was 92% as measured by liquid chromatography. Then, a heat-sensitive recording material was produced in the same manner as in Example 1 except for 5 using the above-mentioned composition in place of the urea-urethane compound synthesized in Example 1, and was evaluated. The results obtained are summarized in Table 1. Example 10 10 To 17 g of 2,4-toluene diisocyanate was added 40 g of methyl ethyl ketone as a solvent, followed by adding dropwise thereto 3.8 g of methanol, and the reaction was carried out with stirring at 60 0 C for 5 hours. Then, 9.9 g of 4,4'-diaminodiphenyl sulfone was 15 added thereto, and the reaction was carried out with stirring at 60*C for 4 hours. After completion of the reaction, the methyl ethyl ketone as solvent was removed by the use of an evaporator, and the residue was dried overnight in a vacuum to obtain 16 g of a 20 urea-urethane composition as white crystals. The melting point of the white crystals was 169 0 C. In IR analysis on the crystals, characteristic peaks due to a urea-urethane compound appeared at 1660 cm-1 and 1740 cm-1. The content of the urea-urethane main constituent 25 in the urea-urethane composition was 52% as measured by liquid chromatography. Then, a heat-sensitive recording material was 274 produced in the same manner as in Example 1 except for using the above-mentioned composition in place of the urea-urethane compound synthesized in Example 1, and was evaluated. The results obtained are summarized in 5 Table 1. Example 11 In 253 mL of toluene was dissolved 27.5 g of 2,4-toluene diisocyanate, followed by adding dropwise thereto a solution of 14.7 g of aniline in 85 mL of 10 toluene at 400C with stirring at 200 rpm over a period of 30 minutes, and the reaction was carried out for another 30 minutes. To the thus obtained white slurry were added 18.0 g of 2,2-bis(4-hydroxyphenyl)propane, 262 mL of toluene and 0.42 mg of triethylamine as 15 catalyst, and the stirring rate was increased to 400 rpm. In order to prevent the aggregation of particles in the slurry in the initial reaction by controlling the reaction rate, the reaction was carried out while raising the reaction temperature stepwise as follows: 20 600C for 5 h, 650C for 2 h, 700C for 1 h, and 75*C for 1 h. Then, 0.42 mg of triethylamine was added, and the reaction was carried out at 800C for another 8 h. The reaction mixture was cooled to room temperature and the resulting white crystals were recovered by filtration. 25 The white crystals were dried overnight in a vacuum to obtain 59 g of a urea-urethane composition as white crystals. The melting point of these white crystals 275 was 170 0 C. In IR analysis on the crystals, a wide characteristic peak due to urea-urethane appeared at 1720 cm'. The content of the urea-urethane main constituent in the urea-urethane composition was 81% as 5 measured by liquid chromatography. Then, a heat-sensitive recording material was produced in the same manner as in Example 1 except for using the above-mentioned composition in place of the urea-urethane compound synthesized in Example 1, and 10 was evaluated. The results obtained are summarized in Table 1. Examples 12 to 23 Heat-sensitive recording materials were produced in the same manner as in Example 8 except for 15 using 4,4'-dichlorodiphenyl sulfone (Example 12), 4,4' dihydroxydiphenyl sulfone (Example 13), 2,4'-dihydroxy diphenyl sulfone (Example 14), 4-(benzyloxy)phenol (Example 15), salicylanilide (Example 16), 4,4' diaminodiphenyl sulfone (Example 17), 4,4'-dichloro 20 benzophenone (Example 18), 4,4'-diaminodiphenylmethane (Example 19), 4,4'-dimethoxybenzophenone (Example 20), diphenyl carbonate (Example 21), 4,4'-dimethoxydiphenyl sulfone (Example 22) or 4,4'-diallyloxydiphenyl sulfone (Example 23) in place of diphenyl sulfone, and the 25 heat-sensitive recording materials were evaluated. The results obtained are summarized in Table 1.
276 Comparative Example 1 A heat-sensitive recording material was produced in the same manner as in Example 1 except for using 2,2-bis(4-hydroxyphenyl)propane in place of the 5 urea-urethane compound synthesized in Example 1, and was evaluated. The results obtained are summarized in Table 1. Comparative Example 2 To 17.4 g of 2,4-toluene diisocyanate was 10 added 5 mL of methyl ethyl ketone as a solvent, followed by adding dropwise thereto a solution of 3.2 g of methanol in 5 mL of methyl ethyl ketone, and the reaction was carried out with stirring at room tempera ture for 2 hours. Then, a solution of 7.3 g of n 15 butylamine in 100 mL of methyl ethyl ketone was added dropwise thereto with stirring at room temperature, and the resulting mixture was stirred for 1 hour. The crystals precipitated were recovered by filtration, washed with hexane and then dried overnight in a vacuum 20 to obtain 27 g of a compound as white crystals. The melting point of the white crystals was 156 0 C, and their analytical measurement was as follows. Result of IR measurement: Characteristic peaks appeared at 1240 cm-', 25 1550 cm', 1640 cm~1, 1720 cm-1 and 3300 cm 1 . The presumed structural formula of the major component of this compound is the formula (R-1) shown 277 hereinafter. Then, a heat-sensitive recording material was produced in the same manner as in Example 1 except for using the compound obtained above, in place of the 5 urea-urethane compound synthesized in Example 1, and was evaluated. The results obtained are summarized in Table 1. Comparative Example 3 To 10.0 g of 2,4-toluene diisocyanate was 10 added 100 g of toluene. While stirring the resulting mixture at 25 0 C, a solution of 15.5 g of stearylamine in 100 mL of toluene was added thereto, and the reaction was continued at 25 0 C for 22 hours. After completion of the reaction, the white solid 15 precipitated was recovered by filtration, washed with toluene and then dried overnight in a vacuum to obtain 20.4 g of white crystals. Thereafter, 5 g of the thus obtained compound was added to 50 mL of methyl ethyl ketone. While stirring the resulting mixture at 80*C, 20 a solution of 8.6 g of p-hydroxybenzylcarboxylic acid in 20 ml of methyl ethyl ketone and then 5 mg of dibutyltin laurate as catalyst were added thereto, and the reaction was continued at 80 0 C for 12 hours. After completion of the reaction, the reaction mixture was 25 cooled to room temperature, and the crystals precipitated were recovered by filtration, washed with methyl ethyl ketone and then dried overnight in a 278 vacuum to obtain 5.6 g of white crystals. Analytical measurements of these white crystals were as follows. Result of IR measurement: 5 Characteristic peaks appeared at 1220 cm~', 1520 cm-1, 1630 cm~1, 1710 cn~, 2900 cm-1 and 3300 cm-1. Result of mass spectrum measurement: [M+H]* was detected at m/z 596. The presumed structural formula of the major 10 component of this compound is the formula (R-2) shown hereinafter. A heat-sensitive recording material was produced in the same manner as in Example 1 except for using the compound obtained above, in place of the 15 urea-urethane compound synthesized in Example 1, and was evaluated. The results obtained are summarized in Table 1. Comparative Example 4 To 100 mL of dioxane was added 3.0 g of p 20 aminophenol. While stirring the resulting mixture at 50*C, a solution of 5.4 g of toluene sulfonylisocyanate in 30 mL of dioxane was added dropwise thereto over a period of 1 hour, and the reaction was continued at 50 0 C for 5 hours. After completion of the reaction, 25 the reaction solution was concentrated and then poured into hexane to effect crystallization, and the solid precipitated was recovered by filtration, washed with 279 hexane and then dried overnight in a vacuum to obtain 4.9 g of brown crystals. Thereafter, 2 g of the thus obtained compound was added to 50 mL of dioxane. While stirring the resulting mixture at 80'C, a solution of 5 3.8 g of octadecyl isocyanate in 10 mL of dioxane and then 2 mg of dibutyltin laurate as catalyst were added thereto, and the reaction was continued at 80*C for 20 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and the 10 crystals precipitated were recovered by filtration, washed with dioxane and then dried overnight in a vacuum to obtain 2.7 g of slightly pink crystals. Analytical measurement of these slightly pink crystals was as follows. 15 Result of IR measurement: Characteristic peaks appeared at 1230 cm~1, 1470 cm~1, 1510 cm~ 1 , 1570 cm- 1 , 1620 cm 1 , 1700 cm', 2900 cm' and 3300 cm-'. The presumed structural formula of the major 20 component of this compound is the formula (R-3) shown below. A heat-sensitive recording material was produced in the same manner as in Example 1 except for using the compound obtained above, in place of the 25 urea-urethane compound synthesized in Example 1, and was evaluated. The results obtained are summarized in Table 1.
280
CH
3 (R-1) 0 O 11 In
H
3 C-O CsN N C N-n-C 4 H H H H C H 3 C (R-2) HO-C- 0 N N N-(CH 2
)
1 7
CH
3 H H H 0 0 11 It 0 (R-3) C 1 2
H
25 -yNCO C \ N- CH3 H _ H H 11 - H Comparative Example 5 To 10 g of 2,4-toluene diisocyanate was added 50 g of toluene as a solvent, followed by adding thereto 30 g of aniline, and the reaction was carried 5 out at 25*C for 3 hours. After completion of the reaction, the white solid precipitated was recovered by filtration, washed with hexane and then dried overnight in a vacuum to obtain 17 g of a compound as white crystals. 10 The presumed structural formula of the major component of this compound is the structural formula of the compound (C-1) shown hereinafter. Next, 2 g of this compound was ground together with 8 g of a 2.5 wt% poly(vinyl alcohol) 15 aqueous solution in a paint shaker for 45 minutes to be dispersed, whereby a dispersion was obtained. Then, a heat-sensitive recording material was 281 produced in the same manner as in Example 1 except for using this dispersion of said compound in place of the dispersion of the compound obtained in Example 1, and was evaluated. The results obtained are summarized in 5 Table 1. Comparative Example 6 To 10 g of 2,4-toluene diisocyanate was added 30 g of toluene as a solvent, followed by adding thereto 30 g of phenol, and the reaction was carried 10 out at 100 0 C for 3 hours. After completion of the reaction, the toluene was removed by concentration and hexane was added to the residue, and the white solid precipitated was recovered by filtration, washed with hexane and then dried overnight in a vacuum to obtain 15 15 g of a compound as white crystals. The presumed structural formula of the major component of this compound is the structural formula of the compound (C-2) shown below. Next, 2 g of the obtained compound was ground 20 together with 8 g of a 2.5 wt% poly(vinyl alcohol) aqueous solution in a paint shaker for 45 minutes to be dispersed, whereby a dispersion was obtained. Then, a heat-sensitive recording material was produced in the same manner as in Example 1 except for 25 using this dispersion of said compound in place of the dispersion of the compound obtained in Example 1, and was evaluated. The results obtained are summarized in 282 Table 1. (C-1) 0 N-C-N CH 3 CO IH H HN, C=O NH 0 (C-2) 0 0-C-N H -Cs HN, CK=o Comparative Example 7 A heat-sensitive recording material was produced in the same manner as in Example 1 except for 5 using 1,3-diphenylurea in place of the urea-urethane compound synthesized in Example 1, and was evaluated. The results obtained are summarized in Table 1.
283 Table 1 Heat resistance Color Plasticizer Preserv developrent resistance Print ability of sensitivity (print preserv- original Total of thenal preserv- ability at recording evaluation paper ability) 60 0 C material surface at 80 0 C Example 1 1.2 0 0 Exaple 2 1.2 0 Example 3 1 . 1 0 0 Exaple 4 1.2 0 @ 0 O Exaple 5 1.2 @ @ @ @ Example 6 1. 2 0 0 Exaple 7 1.2 © 2 0 Exaple 8 1.2 9 @ 0 Exaple 9 1.2 A @ 0 0 Exaple 10 1.2 © @ 0 Example 11 1.2 0 @ 0 ~@ Example 12 1. 2 @ @ © Exaple 13 1.2 0 @ @ O~@ Exaple 14 1. 3 0 @ O~@ O~@ Exaple 15 1. 2 ~ @ 0 0 Exaple 16 1.2 @ @ © Example 17 1 . 1 0 © ~@ Example 18 1.2 @ @ 0 Exaple 19 1. 2 O~@ @ 0-@ O~ Exaple 20 1.3 0 @ @ O~@ Exaple 21 1.2 @ @ @ Example 22 1. 2 @ @ @ Example 23 1.2 @ © © Cmparative 1.3 A-0 Example 1 Comparative 0.3 X A X Example 2 Comparative 0.3 X A 0 X Example 3 Comparative 0 .4 X A 0 X Example 4 Comparative 0.5 0 Example 5 Comparative 0. 4 X x Q X Example 6 Comparative A X Example 7 0 . 6 284 1. Sensitivity becomes higher with an increase of optical density (OD value). 2. Plasticizer resistance (print preservability) @ - Substantially no fading. 5 0 - A slight color tone change without blur and the like. - Marked fading. X - Complete loss of the color of print. 3. Heat resistance (print preservability at 60*C) 10 @ - Substantially no fading. 0 - A slight color tone change without blur and the like. A Marked fading. X - Complete loss of the color of print. 15 4. Heat resistance (the preservability of an original recording material surface at 800C) @ ~ Substantially no fog was caused. o - Reading of a print portion was possible though there was a slight color tone change. 20 A - Reading of a print portion was difficult owing to fog. X - Reading of a print portion was impossible owing to serious fog. Example 24 25 While stirring 31.5 g of 2,4-toluene diisocyanate at 600C, a dilution of 21.5 g of 4,4' diaminodiphenyl sulfone with 120 ml of methyl ethyl 285 ketone was added dropwise thereto over a period of 4 hours, and the reaction was continued at 60 0 C for another 2 hours. After completion of the reaction, the reaction solution was cooled to room temperature and 5 then toluene was added thereto, and the white solid precipitated was recovered by filtration, washed with toluene and then dried overnight in a vacuum to obtain 47 g of a compound as white crystals. Subsequently, 9.5 g of phenol and 95 ml of methyl ethyl ketone were 10 added to 30 g of the obtained compound, followed by adding thereto 30 mg of triethylamine, and the reaction was carried out at 25*C for 4 hours. After completion of the reaction, toluene was added to the reaction solution and the crystals precipitated were recovered 15 by filtration, washed with toluene and then dried overnight in a vacuum to obtain 38.5 g of a compound as white crystals. IR measurement of these white crystals was carried out to find characteristic peaks appeared at 990 cm-', 1110 cm~1, 1320 cm~1, 1590 cm', 1700 cm-' and 20 3350 cm-'. Next, a dispersion was prepared by dispersing 2 g of the obtained compound by grinding it together with 8 g of a 2.5 wt% poly(vinyl alcohol) aqueous solution in a paint shaker for 6 hours. The tempera 25 ture of the dispersion immediately after the dispersing operation was 25 0 C. The diameter of dispersed particles of the compound was 0.6 ptm. Another dispersion was prepared by dispersing 286 70 g of 3 -dibutylamino-6-methyl-7-anilinofluoran by grinding it together with 130 g of a 5.4 wt% aqueous solution of hydroxypropylmethyl cellulose (Metlose 60SH-03, mfd. by Shin-Etsu Chemical Co., Ltd.) in a 5 sand grinder (mfd. by AIMEX CO., LTD.; vessel capacity 400 ml) at a number of revolution of 2,000 rpm for 3 hours. Further another dispersion was prepared by dispersing 70 g of diphenyl sulfone by grinding it 10 together with 130 g of a 8 wt% poly(vinyl alcohol) aqueous solution in a sand grinder (mfd. by AIMEX CO., LTD.; vessel capacity 400 ml) at a number of revolution of 2,000 rpm for 3 hours. Still another dispersion was prepared by 15 mixing 10 g of calcium carbonate with 30 g of water and stirring the mixture by the use of a stirrer. A coating liquid was obtained by stirring and mixing the above-mentioned dispersions and other components in the following proportions (dry basis 20 proportions); the dispersion of the above-mentioned compound in terms of dry solids: 20 parts by weight, the 3 -dibutylamino-6-methyl-7-anilinofluoran dispersion in terms of dry solids: 10 parts by weight, the diphenyl sulfone dispersion in terms of dry solids: 25 25 parts by weight, the calcium carbonate dispersion in terms of dry solids: 40 parts by weight, a zinc stearate dispersion (solid content: 16 wt%) in terms of dry solids: 20 parts by weight, and a 15 wt% poly(vinyl 287 alcohol) in terms of dry solids: 15 parts by weight. The coating liquid was applied on base paper with a basis weight of 50 g/m 2 by the use of a bar coater of rod number 10. The coating amount of the 5 coating liquid was 5 g/m 2 in terms of dry weight. After drying, supercalendering was conducted to obtain a heat-sensitive recording material. The result of evaluating the sensitivity of the heat-sensitive recording material obtained was so 10 good that the optical density was 1.3. The print preservability evaluated by the use of vinyl chloride wrap films was good. The whiteness of the original recording material surface was as good as 82. These evaluation results are summarized in Table 2. 15 Examples 25 and 26 Heat-sensitive recording materials were produced in the same manner as in Example 24 except for using 3 -diethylamino-6-methyl-7-anilinofluoran (Example 25) or 3,3-bis(p-dimethylaminophenyl)-6-dimethylamino 20 phthalide (Example 26) in place of 3-dibutylamino-6 methyl-7-anilinofluoran, and were evaluated. The results obtained are summarized in Table 2. Examples 27 to 29 Heat-sensitive recording materials were 25 produced in the same manner as in Example 24 except for using methyl cellulose (Metlose M-15, mfd. by Shin-Etsu 288 Chemical Co., Ltd.) (Example-27), a polyoxyethylene alkyl ether sulfate (Rebenol WX, mfd. by Kao Corp.) (Example 28) or sodium 2-ethylhexylsulfosuccinate (Neocol SWC, mfd. by Dai-ichi Kogyo Seiyaku Co., Ltd.) 5 (Example 29) in place of the hydroxypropylmethyl cellulose used in Example 24 for dispersing 3 dibutylamino-6-methyl-7-anilinofluoran, and the heat sensitive recording materials were evaluated. The results obtained are summarized in Table 2. 10 Example 30 A urea-urethane compound developer disper sion, a 3 -dibutylamino-6-methyl-7-anilinofluoran dispersion, a diphenyl sulfone dispersion and a calcium carbonate dispersion were prepared in the same manner 15 as in Example 24. On the other hand, a dispersion was prepared by dispersing 70 g of 2,2-bis(4-hydroxyphenyl)propane by grinding it together with 130 g of a 5.4 wt% poly(vinyl alcohol) aqueous solution in a sand grinder 20 (mfd. by AIMEX CO., LTD.; vessel capacity 400 ml) at a number of revolution of 2,000 rpm for 3 hours. A coating liquid was obtained by stirring and mixing the above-mentioned dispersions and other components in the following proportions (dry basis 25 proportions); the urea-urethane compound dispersion in terms of dry solids: 10 parts by weight, the 3 dibutylamino-6-methyl-7-anilinofluoran dispersion in 289 terms of dry solids: 10 parts by weight, the diphenyl sulfone dispersion in terms of dry solids: 20 parts by weight, the 2,2-bis(4-hydroxyphenyl)propane dispersion in terms of dry solids: 10 parts by weight, the calcium 5 carbonate dispersion in terms of dry solids: 20 parts by weight, a zinc stearate dispersion (solid content: 16 wt%) in terms of dry solids: 10 parts by weight, and a 15 wt% poly(vinyl alcohol) in terms of dry solids: 10 parts by weight. 10 A heat-sensitive recording material was produced in the same manner as in Example 24 except for using the coating liquid obtained above, and was evaluated. The results obtained are summarized in Table 2. 15 Examples 31 to 34 Heat-sensitive recording materials were produced in the same manner as in Example 30 except for using 4 -isopropyloxyphenyl-4'-hydroxyphenyl sulfone (D 8, a trade name, mfd. by Nippon Soda Co., Ltd.), 20 (Example 31), bis(3-allyl-4-hydroxyphenyl) sulfone (TG SA, a trade name, mfd. by Nippon Kayaku Co., Ltd.) (Example 32), 2,4'-dihydroxydiphenyl sulfone (24BPS, a trade name, mfd. by Nicca Chemical Co., Ltd.) (Example 33) or a mixture composed mainly of 4,4' 25 [oxybis(ethyleneoxy-p-phenylenesulfonyl)]diphenol
(D
90, a trade name, mfd. by Nippon Soda Co., Ltd.) (Example 34) in place of 2,2-bis(4-hydroxyphenyl)- 290 propane, and the heat-sensitive recording materials were evaluated. The results obtained are summarized in Table 2. Examples 35 to 64 5 Heat-sensitive recording materials were produced in the same manner as in each of Examples 30 to 34 except for using 0-naphthylbenzyl ether (BON, a trade name, mfd. by Ueno Fine Chemicals Industry Ltd.) (Examples 35 to 39), p-benzylbiphenyl (PBBP, a trade 10 name, mfd. by Nippon Steel Chemical Co., Ltd.) (Examples 40 to 44), 1,2-di(m-methylphenoxy)ethane
(KS
235, a trade name, mfd. by SANKOSHA CO., LTD.) (Examples 45 to 49), di-p-methylbenzyl oxalate (HS3520, a trade name, mfd. by Dainippon Ink and Chemicals, 15 Inc.) (Examples 50 to 54), 1,2-diphenoxymethylbenzene (PMB-2, a trade name, mfd. by Nicca Chemical Co., Ltd.) (Examples 55 to 59) or m-terphenyl (mtp, a trade name, mfd. by Nippon Steel Chemical Co., Ltd.) (Examples 60 to 64) in place of diphenyl sulfone, and the heat 20 sensitive recording materials were evaluated. The results obtained are summarized in Table 2. Examples 65 and 66 Heat-sensitive recording materials were produced in the same manner as in Example 24 except for 25 using a stearamide emulsified product (Highmicron G 270, a trade name, mfd. by Chukyo Yushi Co., Ltd.) 291 (Example 65) or acetoacetic o-chloroanilide (mfd. by Mitsuboshi Chemical Co., Ltd.) (Example 66) in place of diphenyl sulfone, and were evaluated. The results obtained are summarized in Table 2. 5 Example 67 A heat-sensitive recording material was produced in the same manner as in Example 30 except for adding a stilbene type fluorescent dye (Kayahol 3BS, a trade name, mfd. by Nippon Kayaku Co., Ltd.) to the 10 coating liquid prepared in Example 30, in a proportion of 1 part by weight per 100 parts by weight (in terms of dry solids) of the coating liquid, and was evaluated. The results obtained are summarized in Table 2. 15 Example 68 A dispersion was obtained by dispersing 70 g of 1,1,3-tris(2-methyl-4-hydroxy-5-tert-butylphenyl) butane by grinding it together with 130 g of a 5.4 wt% poly(vinyl alcohol) aqueous solution in a sand grinder 20 (mfd. by AIMEX CO., LTD.; vessel capacity 400 ml) at a number of revolution of 2,000 rpm for 3 hours. Then, a heat-sensitive recording material was produced in the same manner as in Example 30 except for adding the aforesaid 1,1,3-tris(2-methyl-4-hydroxy-5 25 tert-butylphenyl)butane dispersion to the coating liquid prepared in Example 30, in a proportion of 10 292 parts by weight per 100 parts by weight (in terms of dry solids) of the coating liquid, and was evaluated. The results obtained are summarized in Table 2. Example 69 5 To 30 g of 2,4-toluene diisocyanate was added 30 g of toluene as a solvent, followed by adding thereto 3.24 g of phenol, and the reaction was carried out at 100*C for 1 hour and 30 minutes. After comple tion of the reaction, the toluene was removed by 10 concentration and hexane was added to the residue, and the white solid precipitated was recovered by filtra tion, washed with hexane and then dried overnight in a vacuum to obtain 6.9 g of a compound as white crystals. Subsequently, 100 g of toluene was added as a solvent 15 to 5.0 g of the obtained compound, followed by adding thereto 3.50 g of aniline, and the reaction was carried out at 25*C for 3 hours. The crystals precipitated were recovered by filtration, washed with hexane and then dried overnight in a vacuum to obtain 5.5 g of a 20 compound as white crystals. IR measurement of these white crystals was carried out to find that character istic peaks appeared at 890 cm-1, 1000 cm-', 1030 cm~1, 1440 cm-1, 1720 cm-1 and 3350 cm-. Then, a heat-sensitive recording material was 25 produced in the same manner as in Example 68 except for using the compound obtained above, in place of the urea-urethane compound used in Example 68, and was 293 evaluated. The results obtained are summarized in Table 2. Examples 70 to 75 Heat-sensitive recording materials were 5 produced in the same manner as in Example 68 except for using 1,1,3-tris( 2 -methyl-4-hydroxy-5-cyclohexyl phenyl)butane (Adecaarcles DH-43, mfd. by Asahi Denka Kogyo K.K.) (Example 70), 4-benzyloxy-4'-(2,3-epoxy-2 methylprop-1-yloxy)diphenyl sulfone (NTZ-95, mfd. by 10 Nippon Soda Co., Ltd.), (Example 71), methylenebis(2 hydroxy-3-(benzotriazol-2-yl)-5-tert-octylphenyl) (Example 72), 2-(2'-hydroxy-5'-methylphenyl) benzotriazole (Adecaarcles DN-13, mfd. by Asahi Denka Kogyo K.K.) (Example 73), 1,3,5-tris(2,6-dimethyl-4 15 tert-butyl-3-hydroxybenzyl) isocyanurate (Adecaarcles DH-48, mfd. by Asahi Denka Kogyo K.K.) (Example 74) or sodium 2,2-methylenebis(4,6-di-tert-butylphenyl) phosphate (Adecaarcles F-85, mfd. by Asahi Denka Kogyo K.K.) (Example 75) in place of 1,1,3-tris(2-methyl-4 20 hydroxy-5-tert-butylphenyl)butane, and the heat sensitive recording materials were evaluated. The results obtained are summarized in Table 2. Comparative Example 8 A heat-sensitive recording material was 25 produced in the same manner as in Example 24 except for using 2
,
2 -bis(4-hydroxyphenyl)propane in place of the 294 urea-urethane compound synthesized in Example 24, and was evaluated. The results obtained are summarized in Table 2. Table 2 Plasticizer Sensitivity resistance Total of thermal (print Whiteness evaluation paper preserv ability) Example 24 1.3 @ 82 @ Example 25 1.3 @ 81 @ Example 26 1.3 @ 82 Example 27 1.3 © 82 Example 28 1.3 @ 82 @ Example 29 1.3 @ 82 @ Example 30 1.3 0-@ 81 0 Example 31 1.3 0~@ 81 0 Example 32 1.3 0~ @ 81 0 Example 33 1.3 O~© 81 0 Example 34 1.2 @ 81 0 Example 35 1. 4 0 82 O0~@ Example 36 1.4 0~@ 83 0 Example 37 1. 4 O~© 82 0 ~@ Example 38 1.3 O~© 82 0 ~_@ Example 39 1.2 @ 82 ~ Example 40 1.3 O~@ 82 0~@ Example 41 1.3 ~ 83 O Example 42 1.3 O~@ 82 O Example 43 1.3 0~@ 82 O Example 44 1.2 @ 82 0 Example 45 1.3 0~@ 83 O Example 46 1.3 O~@ 83 ~ Example 47 1.3 O~@ 82 O Example 48 1.3 O~@ 82 O Example 49 1.2 @ 82 O~@ Example 50 1.3 O @ 83 Example 51 1.4 O @ 82 0 Example 52 1. 4 O~@ 82 O Example 53 1.3 O~ 82 Example 54 1.2 © 82 O Example 55 1.3 0~@ 83 O Example 56 1.3 0~@ 82 O Example 57 1. 3 ~ 82 O Example 58 1.3 ~ @ 82 O Example 59 1.2 @ 82 O~@ Example 60 1.3 O~@ 82 0~@ 295 Plasticizer Sensitivity resistance Total of thermal (print Whiteness evaluation paper preserv ability) Example 61 1.3 ~ 82 ~ Example 62 1.3 O~@ 82 Example 63 1.3 O~@ 82 ~ Example 64 1.2 @ 82 ~ Example 65 1.3 Q~@ 83 @ Example 66 1.2 @ 82 @ Example 67 1.3 0 ~@ 85 0 ~@ Example 68 1.3 © 82 @ Example 69 1.3 © 82 © Example 70 1.3 @ 82 @ Example 71 1.3 @ 82 © Example 72 1.3 © 83 0~@ Example 73 1.3 0~@ 82 ~ Example 74 1.3 Q~ 82 Example 75 1.3 ~ @ 83 O Comparative 1 . 3 X 78 X Example 8 1. Sensitivity becomes higher with an increase of optical density (OD value). 2. Plasticizer resistance (print preservability) @ - Substantially no fading. 5 0 - A slight color tone change without blur and the like. A - Marked fading. X - Complete loss of the color of print. 3. Whiteness becomes higher with an increase of its 10 numeral value. Whiteness is sufficient in practice when its numeral value is 80 or more. <Rub resistance> The surface of a heat-sensitive recording material was strongly rubbed with a nail, and whether 296 color development had been caused in the rubbed portion was visually judged. When the recording material showed no remarkable trace of the rubbing, it was rated good in rub resistance. 5 <Accumulation of traces of rubbing> A cylinder (weight: 2 kg) having a face with a diameter of 5 cm was moved 50 times on one and the same portion with a length of 20 cm of the recording surface of each heat-sensitive recording material 10 produced, at a rate of 20 cm/sec, and then the record ing material was allowed to stand at room temperature for one week. After one week of the standing, whether a printed image could be read was visually judged. When the printed image could be sufficiently read, the 15 recording material was rated good. Example 76 A heat-sensitive coating liquid was obtained in the same manner as in Example 24. Then, the coating liquid was applied on base paper with a basis weight of 20 50 g/m 2 by the use of a bar coater of rod number 10. After drying, supercalendering was conducted to form a heat-sensitive color-producing layer on the substrate. The coating amount of the coating liquid was 5 g/m 2 in terms of dry weight. 25 Then, a dispersion was prepared by dispersing 40 g of kaolin by grinding it together with 60 g of a 0.7 % sodium hexametaphosphate aqueous solution in a 297 sand grinder (mfd. by AIMEX CO., LTD.; vessel capacity 400 ml) at a number of revolution of 2,000 rpm for 3 hours. A coating liquid for forming a protective 5 layer was obtained by stirring and mixing the kaolin dispersion and other components in the following proportions (dry basis proportions); the kaolin dispersion in terms of dry solids: 20 parts by weight, a zinc stearate dispersion (solid content: 16 wt%) in 10 terms of dry solids: 10 parts by weight, a carboxy modified poly(vinyl alcohol) aqueous solution in terms of dry solids: 40 parts by weight, and a polyacryl amidoepichlorohydrin crosslinking agent aqueous solution in terms of dry solids: 5 parts by weight. 15 The coating liquid for forming a protective layer was applied on the heat-sensitive color-producing layer by the use of a bar coater of rod number 5. After drying, supercalendering was conducted to obtain a heat-sensitive recording material. The coating 20 amount of the coating liquid for forming a protective layer was 2 g/m 2 in terms of dry weight. The result of evaluating the sensitivity of the heat-sensitive recording material obtained was so good that the optical density was 1.3. The print 25 preservability evaluated by the use of vinyl chloride wrap films was good. The surface of the heat-sensitive recording material was strongly rubbed with a nail and whether color development had been caused in the rubbed 298 portion was visually judged to find that there was no remarkable trace of the rubbing, namely, the rub resistance was good. The result of a long-term test for evaluating the rub resistance was so good that a 5 printed image could be sufficiently read. These evaluation results are summarized in Table 3. Examples 77 and 78 Heat-sensitive recording materials were produced in the same manner as in Example 76 except for 10 using a poly(vinyl alcohol) (Example 77) or an acrylic copolymer (Example 78) in place of the carboxy-modified poly(vinyl alcohol), and were evaluated. The results obtained are summarized in Table 3. Examples 79 to 81 15 Heat-sensitive recording materials were produced in the same manner as in Example 76 except for using aluminum hydroxide (Example 79), a crosslinkable poly(methyl methacrylate) resin (Example 80) or silica dioxide (Example 81) in place of kaolin, and were 20 evaluated. The results obtained are summarized in Table 3. Example 82 A coating liquid for intermediate layer was obtained by stirring and mixing a 33 wt% calcined 25 kaolin dispersion and a 50 wt% styrene/butadiene based 299 latex aqueous dispersion in proportions (dry basis proportions) of 100 parts by weight and 12 parts by weight, respectively. Then, a back coating liquid was obtained by 5 stirring and mixing a 20 wt% acrylic emulsion and a 10 wt% silica fine powder dispersion (Fineseal SP-10) in proportions (dry basis proportions) of 100 parts by weight and 7 parts by weight, respectively. The aforesaid coating liquid for intermediate 10 layer was applied on one side of base paper (50 g/m 2 ) in an amount of 10 g/M' 2 in terms of solids and dried, and the heat-sensitive coating liquid prepared in Example 76 was applied on the same side in an amount of 5 g/m 2 in terms of solids and dried, after which the coating 15 liquid for protective layer prepared in Example 76 was applied on the same side in an amount of 2 g/m 2 in terms of solids and dried. Then, the aforesaid back coating liquid was applied on the uncoated side in an amount of 1 g/m 2 in terms of solids and dried, and calendering was 20 conducted to produce a heat-sensitive recording material, which was evaluated. The results obtained are summarized in Table 3. Comparative Example 9 A heat-sensitive recording material was 25 produced in the same manner as in Example 76 except that no coating liquid for forming a protective layer was applied on the heat-sensitive color-producing 300 layer, and the recording material was evaluated. The results obtained are summarized in Table 3. Table 3 Plasticizer Sensitivity resistance Rub Accumulation Total of thermal (print Resistance of traces of evaluation paper preserv- rubbing ability) Example 76 1.3 @ @ @ Example 77 1.3 @ © @ @ Example 78 1.3 0 @ Example 79 1. 3 @ @ @ Example 80 1.3 0-© @ 0-@ Example 81 1.3 @ 5 @ Example 82 1. 4 @ @ @ Comparative 1.3 A X -A Example 9 1. Sensitivity becomes higher with an increase of optical density (OD value). 5 2. Plasticizer resistance (print preservability) @ - Substantially no fading. o - A slight color tone change without blur and the like. A - Marked fading. 10 X - Complete loss of the color of print. 3. Rub resistance @ - A trace of rubbing shows no development of a black color. o - A trace of rubbing shows slight color develop 15 ment but is not remarkable. A ~ A trace of rubbing shows color development to a limited extent and is remarkable.
301 X - A trace of rubbing shows development of a black color and is remarkable. 4. Accumulation of traces of rubbing @ - A good result is obtained without difficulty in 5 reading a printed image. 0 - Traces of rubbing show slight color development but a printed image can be sufficiently read. - ~ Traces of rubbing show color development, so that a printed image is difficult to read. 10 X - Traces of rubbing show development of a black color, so that a printed image cannot be read. Example 83 A dispersion was prepared by dispersing 2 g of the compound obtained in Example 24, by grinding it 15 together with 8 g of a 2.5 wt% aqueous solution of a poly(vinyl alcohol) (Gohsenol KL-05, mfd. by The Nippon Synthetic Chemical Industry Co., Ltd.) in a paint shaker for 6 hours. The temperature of the dispersion immediately after the dispersing operation was 25*C and 20 the pH of the dispersion was 8. The diameter of dispersed particles of the compound was 0.6 pm. Another dispersion was prepared by dispersing 70 g of 3 -dibutylamino-6-methyl-7-anilinofluoran by grinding it together with 130 g of a 5.4 wt% poly(vinyl 25 alcohol) aqueous solution in a sand grinder (mfd. by AIMEX CO., LTD.; vessel capacity 400 ml) at a number of revolution of 2,000 rpm for 3 hours.
302 Further another dispersion was prepared by dispersing 70 g of diphenyl sulfone by grinding it together with 130 g of a 5.4 wt% aqueous solution of a poly(vinyl alcohol) (Gohsenol KL-05, mfd. by The Nippon 5 Synthetic Chemical Industry Co., Ltd.) in a sand grinder (mfd. by AIMEX CO., LTD.; vessel capacity 400 ml) at a number of revolution of 2,000 rpm for 3 hours. Still another dispersion was prepared by mixing 10 g of calcium carbonate with 30 g of water and 10 stirring the mixture by the use of a stirrer. A coating liquid was obtained by stirring and mixing the above-mentioned dispersions and other components in the following proportions (dry basis proportions); the dispersion of the above-mentioned 15 compound in terms of dry solids: 30 parts by weight, the 3 -dibutylamino-6-methyl-7-anilinofluoran dispersion in terms of dry solids: 15 parts by weight, the diphenyl sulfone dispersion in terms of dry solids: 30 parts by weight, the calcium carbonate dispersion in 20 terms of dry solids: 20 parts by weight, a zinc stearate dispersion (solid content: 16 wt%) in terms of dry solids: 10 parts by weight, and a 15 wt% poly(vinyl alcohol) in terms of dry solids: 7 parts by weight. The pH of the coating liquid was 8.2. 25 Then, the coating liquid was applied on the surface of woodfree paper with a basis weight of 50 g/m 2 in an amount of 5 g/m 2 in terms of dry weight and dried, followed by supercalendering, to produce a heat- 303 sensitive recording material. The result of evaluating the color development sensitivity of the heat-sensitive recording material obtained was so good that the optical density was 1.3. The print preservability 5 evaluated by the use of vinyl chloride wrap films was so good that no fading occurred. The results obtained are summarized in Table 4. Example 84 A dispersion was prepared by dispersing 2 g 10 of the same urea-urethane compound as used in Example 83 and 2 g of diphenyl sulfone by grinding them together with 16 g of a 2.5 wt% aqueous solution of a modified poly(vinyl alcohol) (Gohsenol KL-05, mfd. by The Nippon Synthetic Chemical Industry Co., Ltd.) in a 15 paint shaker for 6 hours. Then, a heat-sensitive recording material was produced in the same manner as in Example 83 except for adding the aforesaid co-dispersion in a proportion of 60 parts by weight in terms of dry solids, in place of 20 the dispersion of the urea-urethane compound used in Example 83 and the diphenyl sulfone dispersion, and the recording material was evaluated. The results obtained are summarized in Table 4. Example 85 25 To 61 g of 2,4-toluene diisocyanate was added 450 g of toluene as a solvent, followed by adding 304 dropwise thereto a solution of 26 g of aniline in 150 g of toluene over a period of 6 hours, and the reaction was carried out at 5'C for 7 hours. After completion of the reaction, the white solid precipitated was 5 recovered by filtration, washed with toluene and then dried overnight in a vacuum to obtain 70 g of a compound as white crystals. Subsequently, 365 g of toluene was added as a solvent to 30 g of the obtained compound, followed by adding thereto 12.2 g of 2,2 10 bis(4-hydroxyphenyl)propane and 0.3 mg of triethyl amine, and the reaction was carried out with stirring at 60 0 C for 4 hours, at 70 0 C for 3 hours, and then at 80 0 C for 3 hours. After completion of the reaction, the reaction solution was cooled to room temperature, 15 and the crystals precipitated were recovered by filtration, washed with toluene and then dried overnight in a vacuum to obtain 42 g of a compound as white crystals. IR measurement of these white crystals was carried out to find that characteristic peaks 20 appeared at 750 cm-1, 840 cm', 1020 cm-1, 1500 cm', 1600 cm-1, 1720 cm' and 3320 cm~1. A dispersion was prepared by dispersing 2 g of this compound and 2 g of diphenyl sulfone by grind ing them together with 16 g of a 2.5 wt% aqueous 25 solution of a modified poly(vinyl alcohol) (Gohseran L 3266, mfd. by The Nippon Synthetic Chemical Industry Co., Ltd.) in a paint shaker for 6 hours. Then, a heat-sensitive recording material was 305 produced in the same manner as in Example 83 except for adding the co-dispersion of the above-mentioned compound and dipheny sulfone in a proportion of 60 parts by weight in terms of dry solids, in place of the 5 dispersion of the urea-urethane compound used in Example 83 and the diphenyl sulfone dispersion, and the recording material was evaluated. The results obtained are summarized in Table 4. Example 86 10 A dispersion was prepared by dispersing 2 g of the compound obtained in Example 69 and 2 g of dimethylbenzyl oxalate by grinding them together with 16 g of a 2.5 wt% aqueous solution of a modified poly(vinyl alcohol) (Gohseran L-3266, mfd. by The 15 Nippon Synthetic Chemical Industry Co., Ltd.) in a paint shaker for 6 hours. Then, a heat-sensitive recording material was produced in the same manner as in Example 83 except for adding the co-dispersion of the above-mentioned 20 compound and dimethylbenzyl oxalate in a proportion of 60 parts by weight in terms of dry solids, in place of the dispersion of the urea-urethane compound used in Example 83 and the diphenyl sulfone dispersion, and the recording material was evaluated. The results obtained 25 are summarized in Table 4.
306 Example 87 A dispersion was prepared by dispersing 2 g of the compound obtained in Example 2, by grinding it together with 8 g of a 2.5 wt% aqueous solution of 5 methyl cellulose (Metlose SM-15, mfd. by Shin-Etsu Chemical Co., Ltd.) in a paint shaker for 6 hours. Then, a heat-sensitive recording material was produced in the same manner as in Example 83 except for using the dispersion of the aforesaid compound in place 10 of the dispersion of the urea-urethane compound used in Example 83, and the recording material was evaluated. The results obtained are summarized in Table 4. Examples 88 to 92 Heat-sensitive recording materials were 15 produced in the same manner as in Example 83 except for using a polycarboxylic acid ammonium salt (Dispersant 5027, mfd. by Sunnopco Co., Ltd.) (Example 88), a water-soluble low-molecular weight copolymer (Discort N14, mfd. by Dai-ichi Kogyo Seiyaku Co., Ltd.) (Example 20 89), sodium 2-ethylhexylsulfosuccinate (Neocol SWC, mfd. by Dai-ichi Kogyo Seiyaku Co., Ltd.) (Example 90), hydroxypropylmethyl cellulose (Metlose 60SH-03, mfd. by Shin-Etsu Chemical Co., Ltd.) (Example 91), or condensed sodium naphthalenesulfonate (Roma D, mfd. by 25 Sunnopco Co., Ltd.) (Example 92) in place of the poly(vinyl alcohol) (Gohsenol KL-05, mfd. by The Nippon Synthetic Chemical Industry Co., Ltd.) used as a 307 dispersing agent for the urea-urethane compound in Example 83, and the heat-sensitive recording materials were evaluated. The results obtained are summarized in Table 4. 5 Examples 93 to 98 Heat-sensitive recording materials were produced in the same manner as in Example 83 except for using methyl cellulose (Metlose SM-15, mfd. by Shin Etsu Chemical Co., Ltd.) (Example 93), a water-soluble 10 low-molecular weight copolymer (Discort N14, mfd. by Dai-ichi Kogyo Seiyaku Co., Ltd.) (Example 94), sodium 2-ethylhexylsulfosuccinate (Neocol SWC, mfd. by Dai ichi Kogyo Seiyaku Co., Ltd.) (Example 95), hydroxy propylmethyl cellulose (Metlose 60SH-03, mfd. by Shin 15 Etsu Chemical Co., Ltd.) (Example 96), condensed sodium naphthalenesulfonate (Roma D, mfd. by Sunnopco Co., Ltd.) (Example 97) or a polycarboxylic acid ammonium salt (Dispersant 5027, mfd. by Sunnopco Co., Ltd.) (Example 98) in place of the poly(vinyl alcohol) 20 (Gosenol KL-05, mfd. by The Nippon Synthetic Chemical Industry Co., Ltd.) used as a dispersing agent for diphenyl sulfone in Example 83, and the heat-sensitive recording materials were evaluated. The results obtained are summarized in Table 4. 25 Examples 99 to 101 Heat-sensitive recording materials were 308 produced in the same manner as in Example 87 except for using methyl cellulose (Metlose SM-15, mfd. by Shin Etsu Chemical Co., Ltd.) (Example 99), hydroxypropyl methyl cellulose (Metlose 60SH-03, mfd. by Shin-Etsu 5 Chemical Co., Ltd.) (Example 100) or a modified poly(vinyl alcohol) (Gohseran L-3266, mfd. by The Nippon Synthetic Chemical Industry Co., Ltd.) (Example 101) in place of the poly(vinyl alcohol) (Gohsenol KL 05, mfd. by The Nippon Synthetic Chemical Industry Co., 10 Ltd.) used as a dispersing agent for diphenyl sulfone in Example 87, and the heat-sensitive recording materials were evaluated. The results obtained are summarized in Table 4. Example 102 15 A heat-sensitive recording material was produced in the same manner as in Example 99 except for using a modified poly(vinyl alcohol) (Gohseran L-3266, mfd. by The Nippon Synthetic Chemical Industry Co., Ltd.) in place of the methyl cellulose (Metlose SM-15, 20 mfd. by Shin-Etsu Chemical Co., Ltd.) used as a dispersing agent for the urea-urethane compound in Example 99, and the recording material was evaluated. The results obtained are summarized in Table 4. Examples 103 and 104 25 Heat-sensitive recording materials were produced in the same manner as in Example 89 except for 309 using methyl cellulose (Metlose SM-15, mfd. by Shin Etsu Chemical Co., Ltd.) (Example 103) or hydroxy propylmethyl cellulose (Metlose 60SH-03, mfd. by Shin Etsu Chemical Co., Ltd.) (Example 104) in place of the 5 poly(vinyl alcohol) (Gohsenol KL-05, mfd. by The Nippon Synthetic Chemical Industry Co., Ltd.) used as a dispersing agent for diphenyl sulfone in Example 89, and the heat-sensitive recording materials were evaluated. The results obtained are summarized in 10 Table 4. Examples 105 to 106 Heat-sensitive recording materials were produced in the same manner as in Example 91 except for using methyl cellulose (Metlose SM-15, mfd. by Shin 15 Etsu Chemical Co., Ltd.) (Example 105) or hydroxy propylmethyl cellulose (Metlose 60SH-03, mfd. by Shin Etsu Chemical Co., Ltd.) (Example 106) in place of the poly(vinyl alcohol) (Gohsenol KL-05, mfd. by The Nippon Synthetic Chemical Industry Co., Ltd.) used as a 20 dispersing agent for diphenyl sulfone in Example 91, and the heat-sensitive recording materials were evaluated. The results obtained are summarized in Table 4. Examples 107 and 108 25 Heat-sensitive recording materials were produced in the same manner as in Example 104 except 310 for using hydroxypropylmethyl cellulose (Metlose 60SH 03, mfd. by Shin-Etsu Chemical Co., Ltd.) (Example 107) or a mixed dispersing agent of hydroxypropylmethyl cellulose (Metlose 60SH-03, mfd. by Shin-Etsu Chemical 5 Co., Ltd.) and sodium 2-ethylhexylsulfosuccinate (Neocol SWC, mfd. by Dai-ichi Kogyo Seiyaku Co., Ltd.) (weight ratio: 1/1) (Example 108) in place of the poly(vinyl alcohol) used as a dispersing agent for 3 dibutylamino-6-methyl-7-anilinofluoran in Example 104, 10 and the heat-sensitive recording materials were evaluated. The results obtained are summarized in Table 4. Comparative Example 10 A heat-sensitive recording sheet was produced 15 in the same manner as in Example 83 except for using 2,2-bis(4-hydroxyphenyl)propane in place of the urea urethane compound used in Example 83, and was evaluated. The results obtained are summarized in Table 4. 20 Comparative Examples 11 and 12 The same urea-urethane compound as used in Example 83 was dispersed in the same manner as in Example 83 except for changing the dispersion time, and the average particle sizes of the resulting dispersions 25 were measured and found to be 0.04 ptm (Comparative Example 11) and 6.5 pm (Comparative Example 12). Heat- 311 sensitive recording sheets were produced in the same manner as in Example 83 except for using each of the above-mentioned dispersions, and were evaluated. The results obtained are summarized in Table 4. 5 Comparative Example 13 The same urea-urethane compound as used in Example 83 was dispersed in the same manner as in Example 83 except for maintaining the dispersing temperature at 65 0 C during the dispersing operation. 10 Except for using the dispersion thus obtained, a heat sensitive recording sheet was produced in the same manner as in Example 83, and was evaluated. The results obtained are summarized in Table 4. Comparative Example 14 15 The same urea-urethane compound as used in Example 83 was dispersed in the same manner as in Example 83 except for adjusting the pH of the disper sion medium used for the dispersing operation to 4. Except for using the dispersion thus obtained, a heat 20 sensitive recording sheet was produced in the same manner as in Example 83, and was evaluated. The results obtained are summarized in Table 4. Comparative Example 15 The same urea-urethane compound as used in 25 Example 83 was dispersed in the same manner as in 312 Example 83 except for adjusting the pH of the disper sion medium used for the dispersing operation to 11. Except for using the dispersion thus obtained, a heat sensitive recording sheet was produced in the same 5 manner as in Example 83, and was evaluated. The results obtained are summarized in Table 4. Comparative Example 16 The pH of the coating liquid prepared in Example 83 was adjusted to 4.0 with 1N-sulfuric acid. 10 Except for using the coating liquid thus adjusted, a heat-sensitive recording sheet was produced in the same manner as in Example 83, and was evaluated. The results obtained are summarized in Table 4. Comparative Example 17 15 The pH of the coating liquid prepared in Example 83 was adjusted to 12.5 with 1N-sodium hydroxide. Except for using the coating liquid thus adjusted, a heat-sensitive recording sheet was produced in the same manner as in Example 83, and was evaluated. 20 The results obtained are summarized in Table 4.
313 Table 4 Plasticizer Plasticizer resistance resistance Sensitivity of (print (preservability of Total thenial paper preserv- original recording evaluation ability) material surface) Example 83 1. 3 @ -@ Q Example 84 1.4 @ ~@ 0-© Example 85 1.3 O -@ @ O @ Exanrple 86 1.3 0 ~ @ Examrple 87 1.3 0 ~ @0 9 Example 88 1.3 @ 9 Example 89 1.3 @ @ 9 Example 90 1.2 @ @ Example 91 1.3 @ O~@ O~@ Example 92 1.2 © -@ 0-~9 Example 93 1.3 @@ @ Example 94 1 . 3 @ Example 95 1.3 @ @ Example 96 1.3 @ ~ @ 0~@ Example 97 1.3 @ O-@ O @ Exarrple 98 1.3 @ O-@ O @ Example 99 1.3 9 @ Example 100 1.3 © 3 @ Example 101 1. 4 5 @ Example 102 1. 4 @ @ Example 103 1. 3 @ @ Example 104 1.3 9 @ Exarrple 105 1.3 ©@ @ Example 106 1.3 @ @ Example 107 1.3 © @ Example 108 1.4 @ @ Comparative 1. 3 X X Examrple 10 Comparative 1.3 X X Example 11 CorTparative 0 .7 A X Example 12 Comparative 0. 8 X Example 13 Comparative 1. A X X Example 14 Coparative 0 .8 A X Exarrple 15 Cmparative 1. 1 A X Example 16 Comparative 0. 9 X X Example 17 x A 314 1. Sensitivity becomes higher with an increase of optical density (OD value). 2. Plasticizer resistance (print preservability) @ Substantially no fading. 5 0 ~ A slight color tone change without blur and the like. - Marked fading. X ~ Complete loss of the color of print. 3. Plasticizer resistance (the preservability of an 10 original recording material surface) @ - The original recording material surface is hardly colored. 0 ~ The original recording material surface is very slightly colored though there is a subtle color 15 tone change. A - The original recording material surface is markedly colored. X ~ The original recording material surface is so seriously colored that reading of print is 20 difficult. Example 109 The coating liquid prepared in Example 83 was applied on woodfree paper with a surface pH of 3.2 in an amount of 5 g/m 2 in terms of dry weight and dried, 25 followed by supercalendering, to produce a heat sensitive recording material. The result of evaluating the color development sensitivity of the heat-sensitive 315 recording material obtained was so good that the optical density was 1.3. The print preservability evaluated by the use of vinyl chloride wrap films was so good that no fading occurred. The preservability or 5 the original recording material surface was so good that the surface was hardly colored. The results obtained are summarized in Table 5. Examples 110 and 111 Heat-sensitive recording materials were 10 produced in the same manner as in Example 109 except for using woodfree paper with a surface pH of 5 (Example 110) or woodfree paper with a surface pH of 6.8 (Example 111) in place of the woodfree paper with a surface pH of 3.2, and were evaluated. The results 15 obtained are summarized in Table 5. Comparative Examples 18 and 19 Heat-sensitive recording materials were produced in the same manner as in Example 109 except for using woodfree paper with a surface pH of 2.8 20 (Comparative Example 18) or woodfree paper with a surface pH of 9.5 (Comparative Example 19) in place of the woodfree paper with a surface pH of 3.2, and were evaluated. The results obtained are summarized in Table 5.
316 Table 5 Plasticizer Plasticizer Sensitivity of resistance resistance Total thental paper (print (preservability of evaluation preserv- original recording ability) material surface) Example 109 1.3 @ -@ Example 110 1. 3 @ @ Example 111 1.3 @ @ Corparative 1.3 A X Example 18 Comparative 1.0 A Example 19 1 1. Sensitivity becomes higher with an increase of optical density (OD value). 2. Plasticizer resistance (print preservability) @ ~- Substantially no fading. 5 0 - A slight color tone change without blur and the like. A - Marked fading. X - Complete loss of the color of print. 3. Plasticizer resistance (the preservability of an 10 original recording material surface) @ -The original recording material surface is hardly colored. 0 - The original recording material surface is very slightly colored though there is a subtle color 15 tone change. - The original recording material surface is markedly colored. X - The original recording material surface is so seriously colored that reading of print is 317 difficult. Example 112 A) Preparation of a coating liquid for magnetic recording layer 5 A coating liquid for magnetic recording layer was prepared by subjecting 100 parts by weight of barium ferrite (coercive force: 2,700), 25 parts by weight of sodium polyacrylate (a 20 wt% aqueous solution), 100 parts by weight of a poly(vinylidene 10 chloride) (a 49 wt% dispersion), 15 parts by weight of carbon black (a 36 wt% dispersion), 10 parts by weight of paraffin wax (a 20 wt% dispersion obtained by the use of methyl cellulose) and 100 parts by weight of water to dispersion in a ball mill for 10 hours. 15 B) Preparation of a coating liquid for heat-sensitive recording layer A coating liquid for heat-sensitive recording layer was obtained in the same manner as in Example 24. Next, the coating liquid for magnetic record 20 ing layer prepared in A) was applied on one side of woodfree paper with a basis weight of 150 g/m 2 in an amount of 30 g/m 2 in terms of dry weight and dried to obtain a magnetic recording layer. Then, the coating liquid for heat-sensitive recording layer prepared in 25 B) was applied on the other side of the substrate having the aforesaid magnetic recording layer, in an amount of 6 g/m 2 in terms of dry weight and dried, 318 followed by supercalendering, to obtain a heat sensitive magnetic recording material. The result of evaluating the color develop ment sensitivity of the heat-sensitive recording layer 5 of the heat-sensitive magnetic recording material obtained was so good that the optical density was 1.3. The print preservability evaluated by the use of vinyl chloride wrap films was so good that no fading occurred. The results obtained are summarized in Table 10 6. Example 113 C) Preparation of a coating liquid for protective layer Twenty parts by weight of zinc stearate, 20 15 parts by weight of a 5 wt% methyl cellulose aqueous solution and 60 parts by weight of water were mixed and then subjected to dispersion in a sand grinder for 2 hours. Then, 20 parts by weight of a 10 wt% carboxy modified poly(vinyl alcohol) aqueous solution, 1.5 20 parts by weight of silica, 6.5 parts by weight of a 12.5 wt% polyamidoepichlorohydrin aqueous solution and 15.0 parts by weight of water were mixed and then subjected to dispersion in a sand grinder for 2 hours. Subsequently, 0.7 part by weight of the zinc 25 stearate dispersion obtained above, 45.0 parts by weight of the silica dispersion obtained above and 11.3 parts by weight of water were mixed to prepare a 319 coating liquid for protective layer. A heat-sensitive magnetic recording material was produced in the same manner as in Example 112 except for forming a protec tive layer by applying the aforesaid coating liquid for 5 protective layer on the heat-sensitive recording layer of the heat-sensitive magnetic recording material of Example 112 in an amount of 3 g/m 2 in terms of dry weight, followed by drying, and the heat-sensitive magnetic recording material was evaluated. The results 10 obtained are summarized in Table 6. Example 114 D) Preparation of a coating liquid for intermediate layer A coating liquid for intermediate layer was 15 prepared which was composed of 80 parts by weight (in terms of dry solids) of a 48% dispersion of polystyrene fine particles and 20 parts by weight (in terms of dry solids) of a 40% styrene-acrylic ester copolymer emulsion. 20 A heat-sensitive magnetic recording material was produced in the same manner as in Example 113 except for forming an intermediate layer by applying the aforesaid coating liquid between the heat-sensitive recording layer and substrate of the heat-sensitive 25 magnetic recording material of Example 113 in an amount of 8 g/m 2 in terms of dry weight, followed by drying, and the heat-sensitive magnetic recording material was 320 evaluated. The results obtained are summarized in Table 6. Comparative Example 20 A heat-sensitive recording sheet was produced 5 in the same manner as in Example 112 except for using 2,2-bis(4-hydroxyphenyl)propane in place of the urea urethane compound used in Example 112, and was evaluated. The results obtained are summarized in Table 6. Table 6 Plasticizer Sensitivity of resistance Total thermal paper (print evaluation preserv ability) Example 112 1.3 @ @ Example 113 1.2 @ Example 114 1.3 @ @ Comparative 1.3 X X Example 20 10 1. Sensitivity becomes higher with an increase of optical density (OD value). 2. Plasticizer resistance (print preservability) @ ~ Substantially no fading. 0 - A slight color tone change without blur and the 15 like. A - Marked fading. X - Complete loss of the color of print.
321 Example 115 A) Preparation of a coating liquid for heat-sensitive recording layer A coating liquid for heat-sensitive recording 5 layer was obtained in the same manner as in Example 24. The coating liquid for heat-sensitive record ing layer prepared in A) was applied on the surface of woodfree paper with a basis weight of 150 g/m2 in an amount of 7 g/m 2 in terms of dry weight and dried, 10 followed by supercalendering, to produce a sheet coated with a heat-sensitive recording layer. B) Production of a release sheet A mold release agent composed of oily dimethyl silicone was applied on base paper with a 15 basis weight of 40 g/m 2 in an amount of 1 g/m 2 by the use of a gravure coater to form a release layer. Then, an adhesive layer component consisting of 100 parts by weight of chlorinated rubber, 20 parts by weight of ester gum and 120 parts by weight of dibutyl phthalate 20 was applied on the release layer in an amount of 10 g/m 2 C) Production of a label for heat-sensitive recording The uncoated surface of the sheet coated with a heat-sensitive recording layer which had been 25 produced in the above item A) and the surface coated with an adhesive layer of the release sheet produced in the above item B) were stuck together so that they might face each other, whereby a label for heat- 322 sensitive recording was produced. The result of evaluating the color develop ment sensitivity of the obtained label for heat sensitive recording was so good that the optical 5 density was 1.3. The print preservability evaluated by the use of vinyl chloride wrap films was so good that no fading occurred. The results obtained are summarized in Table 7. Example 116 10 D) Preparation of a coating liquid for back coating layer A coating liquid for back coating layer was prepared by mixing 100 parts by weight of a styrene maleic acid copolymer with 50 parts by weight of 15 kaolin. A label for heat-sensitive recording was produced in the same manner as in Example 115 except for forming a back coating layer by applying the aforesaid coating liquid on the side reverse to the side coated with a heat-sensitive recording layer of 20 the label for heat-sensitive recording of Example 115 in an amount of 1 g/m 2 in terms of dry weight, followed by drying, and the label was evaluated. The results obtained are summarized in Table 7. Example 117 25 E) Preparation of a coating liquid for intermediate layer 323 A coating liquid for intermediate layer was prepared which was composed of 80 parts by weight (in terms of dry solids) of a 48% dispersion of polystyrene fine particles and 20 parts by weight (in terms of dry 5 solids) of a 40% styrene-acrylic ester copolymer emulsion. A label for heat-sensitive recording was produced in the same manner as in Example 116 except for forming an intermediate layer by applying the 10 aforesaid coating liquid between the heat-sensitive recording layer and substrate of the label for heat sensitive recording of Example 116 in an amount of 8 g/m 2 in terms of dry weight, followed by drying, and the label was evaluated. The results obtained are 15 summarized in Table 7. Example 118 F) Preparation of a coating liquid for protective layer Twenty parts by weight of zinc stearate, 20 20 parts by weight of a 5 wt% methyl cellulose aqueous solution and 60 parts by weight of water were mixed and then subjected to dispersion in a sand grinder for 2 hours. Then, 20 parts by weight of a 10 wt% carboxy modified poly(vinyl alcohol) aqueous solution, 1.5 25 parts by weight of silica, 6.5 parts by weight of a 12.5 wt% polyamidoepichlorohydrin aqueous solution and 15.0 parts by weight of water were mixed and then 324 subjected to dispersion in a sand grinder for 2 hours. Subsequently, 0.7 part by weight of the zinc stearate dispersion obtained above, 45.0 parts by weight of the silica dispersion obtained above and 11.3 5 parts by weight of water were mixed to prepare a coat ing liquid for protective layer. A label for heat sensitive recording was produced in the same manner as in Example 117 except for forming a protective layer by applying the aforesaid coating liquid on the heat 10 sensitive recording layer of the label for heat sensitive recording of Example 117 in an amount of 3 g/m 2 in terms of dry weight, followed by drying, and the label was evaluated. The results obtained are summarized in Table 7. 15 Comparative Example 21 A heat-sensitive recording sheet was produced in the same manner as in Example 115 except for using 2,2-bis(4-hydroxyphenyl)propane in place of the urea urethane compound used in Example 115, and was 20 evaluated. The results obtained are summarized in Table 7.
325 Table 7 Plasticizer Sensitivity of resistance Total thermal paper (print evaluation preserv ability) Example 115 1.3 0 ~ @ Example 116 1.3 0 ~ ~@ Example 117 1.4 0 ~ Example 118 1.3 @ Comparative 1.3 X X Example 21 1. Sensitivity becomes higher with an increase of optical density (OD value). 2. Plasticizer resistance (print preservability) @ © Substantially no fading. 5 0 - A slight color tone change without blur and the like. A - Marked fading. X - Complete loss of the color of print. Example 119 10 The coating materials for heat-sensitive color-producing layer and coating material for intermediate layer described below were applied on one side of a commercial poly(ethylene terephthalate) film of 75 pm in thickness (Lumilar E, a trade name, Toray 15 Industries, Inc.) so that the following multiple layers might be formed on the substrate in the following order: a cyan color development heat-sensitive record ing layer, an intermediate layer, a magenta color 326 development heat-sensitive recording layer, an inter mediate layer, a yellow color development heat sensitive recording layer, and an intermediate layer. The application was carried out by bar coating so that 5 the coating amounts of each heat-sensitive recording layer and each intermediate layer after drying might be 6.5 g/m 2 and 2.0 g/m 2 , respectively, whereby a multi color heat-sensitive recording material was obtained. - Preparation of a coating material for cyan color 10 development heat-sensitive recording layer Liquid A (a heat-sensitive color-developable dye dispersion) Twenty parts by weight of 3,3-bis(p dimethylaminophenyl)-6-dimethylaminophthalide, 20 parts 15 by weight of a 10% poly(vinyl alcohol) aqueous solution and 10 parts by weight of water were mixed and then subjected to dispersion and grinding in a sand grinder (mfd. by AIMEX CO., LTD.) to prepare a dispersion having an average particle size of 0.7 gm. 20 Liquid B (a developer dispersion) A urea-urethane compound was synthesized in the same manner as in Example 24, and a dispersion was prepared by dispersing 30 g of this compound by grinding it together with 120 g of a 2.5 wt% poly(vinyl 25 alcohol) aqueous solution in a sand grinder for 3 hours. The temperature of the dispersion immediately after the dispersing operation was 25 0 C. The diameter of dispersed particles of the compound was 0.6 pm.
327 A coating material for cyan color development heat-sensitive color-producing layer was prepared by mixing 30 parts by weight of the liquid A, 120 parts by weight of the liquid B, 52 parts by weight of a 60% 5 calcium carbonate slurry, 40 parts by weight of a 10% poly(vinyl alcohol) aqueous solution, 28 parts by weight of an SBR latex (L-1537, a trade name, ASAHI Chemical Industry, Co., Ltd.; solid content 50%), 11 parts by weight of stearamide (Celozol A-877, a trade 10 name, mfd. by Chukyo Yushi Co., Ltd.; solid content 26.5%) and 82 parts by weight of water. Preparation of a coating material for magenta color development heat-sensitive recording layer Liquid A (a heat-sensitive color-developable dye 15 dispersion) Twenty parts by weight of 4-N-(2-(2,4-di tert-amylphenoxy)butyryl)piperazinobenzenediazonium hexafluorophosphate, 20 parts by weight of a 10% poly(vinyl alcohol) aqueous solution and 10 parts by 20 weight of water were mixed and then subjected to dispersion and grinding in a sand grinder to prepare a dispersion having an average particle size of 0.7 prm. Liquid B (a coupler dispersion) Fifty parts by weight of 1-(2'-octylphenyl) 25 3-methyl-5-pyrazolone, 50 parts by weight of 1,2,3 triphenylguanidine, 50 parts by weight of a 10% poly(vinyl alcohol) aqueous solution and 25 parts by 328 weight of water were mixed and then subjected to dispersion and grinding in a sand grinder to prepare a dispersion having an average particle size of 1.0 pm. A coating material for magenta color develop 5 ment heat-sensitive color-producing layer was prepared by mixing 30 parts by weight of the liquid A, 90 parts by weight of the liquid B, 52 parts by weight of a 60% calcium carbonate slurry, 40 parts by weight of a 10% poly(vinyl alcohol) aqueous solution, 28 parts by 10 weight of an SBR latex (L-1537, a trade name, ASAHI Chemical Industry, Co., Ltd.; solid content 50%), 11 parts by weight of stearamide (Celozol A-877, a trade name, mfd. by Chukyo Yushi Co., Ltd.; solid content 26.5%) and 82 parts by weight of water. 15 Preparation of a coating material for yellow color development heat-sensitive recording layer Liquid A (a heat-sensitive color-developable dye dispersion) Twenty parts by weight of 2,5-dibutoxy-4 20 tolylthiobenzenebenzenediazonium hexafluorophosphate, 20 parts by weight of a 10% poly(vinyl alcohol) aqueous solution and 10 parts by weight of water were mixed and then subjected to dispersion and grinding in a sand grinder to prepare a dispersion having an average 25 particle size of 0.7 im. Liquid B (a coupler dispersion) Fifty parts by weight of 2-chloro-5-(3-(2,4- 329 di-tert-pentyl)phenoxypropylamino)acetanilide, 50 parts by weight of 1,2,3-triphenylguanidine, 50 parts by weight of a 10% poly(vinyl alcohol) aqueous solution and 25 parts by weight of water were mixed and then 5 subjected to dispersion and grinding in a sand grinder to prepare a dispersion having an average particle size of 1.0 pm. A coating material for yellow color develop ment heat-sensitive color-producing layer was prepared 10 by mixing 30 parts by weight of the liquid A, 90 parts by weight of the liquid B, 52 parts by weight of a 60% calcium carbonate slurry, 40 parts by weight of a 10% poly(vinyl alcohol) aqueous solution, 28 parts by weight of an SBR latex (L-1537, a trade name, ASAHI 15 Chemical Industry, Co., Ltd.; solid content 50%), 11 parts by weight of stearamide (Celozol A-877, a trade name, mfd. by Chukyo Yushi Co., Ltd.; solid content 26.5%) and 82 parts by weight of water. Preparation of a coating material (solid content: 20 15%) for intermediate layer A coating material for intermediate layer was prepared by mixing 42 parts by weight of a 60% kaolinite clay (average particle size: 0.6 sm) disper sion, 200 parts by weight of a carboxylic acid-modified 25 poly(vinyl alcohol) aqueous solution (Gohsenol T-330, a trade name, mfd. by The Nippon Synthetic Chemical Industry Co., Ltd.; solid content 10%), 100 parts by 330 weight of an acrylic emulsion (SC-2250, a trade name, mfd. by Nippon Shokubai Co., Ltd.; solid content 40%), 33 parts by weight of a dimethylolurea solution (J-001, a trade name, mfd. by Showa Denko K.K.; solid content 5 30%), 13 parts by weight of a 40% zinc stearate disper sion (Highmicron F-930, a trade name, mfd. by Chukyo Yushi Co., Ltd.; average particle size 0.9 pm), 70 parts by weight of heavy calcium carbonate (NS-1000, a trade name, mfd. by Nitto Funka Kogyo Co., Ltd.), 25 10 parts by weight of a urethane acrylate emulsion (EM90, a trade name, mfd. by Arakawa Chemical Industries Ltd.; solid content 40%), 5 parts by weight of a polysiloxane (SM7025, a trade name, mfd. by Dow Corning Toray Silicone Co., Ltd.; solid content 33%) and 40 parts by 15 weight of water. Example 120 An example of the production of a two-color heat-sensitive recording material is described below. (A) Leuco dye for high-temperature color 20 producing layer: 3-(4'-dibutylamino-2'-hydroxyphenyl) 3-(S'-anilino- 4 '-methyl-2'-methoxyphenyl)phthalide. (B) Leuco dye for low-temperature color producing layer: 3-diethylamino-7-chlorofluoran. (C) Developer: the urea-urethane compound 25 synthesized in Example 119. (D) Sensitizer: diphenyl sulfone. Forty grams of each of the above-mentioned 331 organic compounds (A) to (D) was mixed with 40 g of a 10% poly(vinyl alcohol) solution (degree of polymer ization 500, and degree of saponification 90%) and 20 g of water, and each of the thus obtained compositions 5 was subjected to dispersion in a vertical sand mill (a sand grinder manufactured by AIMEX CO., LTD.) so that the particle size might be 1 pm, whereby dispersions were prepared as liquids (A) to (D) corresponding to the compounds (A) to (D), respectively. 10 On the other hand, 40 g of light calcium carbonate (Brilliant 15, mfd. by Shiraishi Industrial Co., Ltd.; average particle size 0.15 pm) and 60 g of a 0.7% sodium hexametaphosphate solution were mixed, and the resulting composition was subjected to dispersion 15 in a Cowles dispersing machine. Separately, a 21% zinc stearate dispersion was prepared as a lubricant dispersion, a liquid (F), and a 10% poly(vinyl alcohol (NM11, mfd. by The Nippon Synthetic Chemical Industry Co., Ltd.) was prepared as 20 an adhesive liquid (G). Preparation of a coating liquid (I) for high temperature color development heat-sensitive layer A coating liquid for high-temperature color development heat-sensitive layer was prepared by 25 blending the above-mentioned liquids (A), (C), (D) and (G) so that their weight ratio after drying might be as follows: (A) : (C) : (E) : (G) = 20 : 40 : 25 : 15.
332 Formation of a high-temperature color development heat-sensitive layer A high-temperature color development heat sensitive layer was formed by applying the aforesaid 5 coating liquid (I) for high-temperature color develop ment heat-sensitive layer on woodfree paper (neutral paper) with a basis weight of 60 g/m 2 in an amount of 8 g/m 2 in terms of dry weight by means of a Mayer bar. Preparation of a coating liquid (II) for low 10 temperature color development heat-sensitive layer A coating liquid for low-temperature color development heat-sensitive layer was prepared by blending the above-mentioned liquids (B), (C), (D), (E), (F) and (G) so that their weight ratio after 15 drying might be as follows: (B) : (C) : (D) : (E) (F) : (G) = 10 : 20 : 20 : 20 : 10 : 10. Production of a two-color heat-sensitive recording material The coating liquid (II) for low-temperature 20 color development heat-sensitive layer was applied on the above-mentioned high-temperature color development heat-sensitive layer in an amount of 5 g/m 2 in terms of dry weight. Then, the Bekk smoothness (JIS-P8119) of the heat-sensitive recording surface was adjusted to 25 150 seconds by smoothing treatment by means of a supercalender, whereby a two-color heat-sensitive recording material was obtained.
333 Comparative Example 22 A multicolor heat-sensitive recording material was produced in the same manner as in Example 119 except for using 2,2-bis(4-hydroxyphenyl)propane in 5 place of the urea-urethane compound synthesized in Example 119, and was evaluated. The results obtained are summarized in Table 8. Comparative Example 23 A two-color heat-sensitive recording material 10 was produced in the same manner as in Example 120 except for using 2,2-bis(4-hydroxyphenyl)propane in place of the urea-urethane compound used in Example 120, and was evaluated. The results obtained are summarized in Table 8. 15 Evaluation of the multicolor heat-sensitive recording materials The multicolor heat-sensitive recording materials obtained in Examples 119 and 120 and Compara tive Examples 22 and 23 were subjected to printing by 20 the use of a commercial thermal printer (NC-1, a trade name, mfd. by Fuji Photo Film Co., Ltd.), and the quality of image and the image preservability were evaluated by the following methods. <Quality of image> 25 For 5 sheets of each recording material, the definition, contrast, density nonuniformity of image, 334 and the like were visually judged and they were evaluated in the following 5 grades; 0: good, O-A: somewhat good, A: mediocre, A-X: somewhat bad, X: bad. 5 <Image preservability> Each recording material was held between vinyl chloride wrap films or in a vinyl chloride file, and a load of 300 g/cm 2 was applied thereto from above. After standing at 40 0 C for 24 hours, the coloring 10 density of the printed portion and the non-printed portion (the original recording material surface) was visually estimated. When there was only a slight decrease in print density, the image preservability was rated good. 15 The results obtained are as shown in Table 8. That is, the recording materials of Examples 119 and 120 were good in quality of image and exhibited an excellent image preservability, while the recording materials of Comparative Examples 22 and 23 were 20 inferior to the recording materials of Examples 119 and 120. Table 8 Quality of Image Total image preservability evaluation Example 119 0 @ @ Example 120 0 © @ Comparative X Example 22 Comparative Example 23 335 1. Quality of image o -- Good. A - Mediocre. X -- Bad. 5 2. Print preservability @ - Substantially no fading. o - A slight color tone change without blur and the like. - Marked fading. 10 X - Complete loss of the color of print. Example 121 A urea-urethane compound was synthesized in the same manner as in Example 24, and a dispersion was prepared by dispersing 2 g of this compound by grinding 15 it together with 8 g of a 2.5 wt% poly(vinyl alcohol) aqueous solution in a paint shaker for 6 hours. The temperature of the dispersion immediately after the dispersing operation was 25 0 C. The diameter of dispersed particles of the compound was 0.6 tm. 20 Another dispersion was prepared by dispersing 70 g of 3 -dibutylamino-6-methyl-7-anilinofluoran by grinding it together with 130 g of a 5.4 wt% poly(vinyl alcohol) aqueous solution in a sand grinder (mfd. by AIMEX CO., LTD.; vessel capacity 400 ml) at a number of 25 revolution of 2,000 rpm for 3 hours. Further another dispersion was prepared by dispersing 70 g of diphenyl sulfone by grinding it 336 together with 130 g of a 5.4 wt% poly(vinyl alcohol) aqueous solution in a sand grinder (mfd. by AIMEX CO., LTD.; vessel capacity 400 ml) at a number of revolution of 2,000 rpm for 3 hours. 5 Still another dispersion was prepared by mixing 10 g of calcium carbonate with 30 g of water and stirring the mixture by the use of a stirrer. On the other hand, an aluminum hydroxide dispersion was prepared by treating a mixture of 60 10 parts by weight of aluminum hydroxide and 40 parts by weight of a 12.5 wt% poly(vinyl alcohol) aqueous solution for 2 hours by the use of a sand grinder to disperse aluminum hydroxide so that the average particle size might be about 1 pm. 15 A coating liquid was obtained by stirring and mixing the above-mentioned dispersions and other components in the following proportions (dry basis proportions); the dispersion of the above-mentioned compound in terms of dry solids: 20 parts by weight, 20 the 3-dibutylamino-6-methyl-7-anilinofluoran dispersion in terms of dry solids: 10 parts by weight, the diphenyl sulfone dispersion in terms of dry solids: 25 parts by weight, the calcium carbonate dispersion in terms of dry solids: 40 parts by weight, the aluminum 25 hydroxide dispersion in terms of dry solids: 13 parts by weight, a zinc stearate dispersion (solid content: 16 wt%) in terms of dry solids: 20 parts by weight, and a 15 wt% poly(vinyl alcohol) in terms of dry solids: 15 337 parts by weight. Subsequently, this coating liquid for heat sensitive recording layer was applied on aluminized paper at a rate of 50 m/min by the use of a gravure 5 coater (200 mesh; plate depth 20 pL). The aluminized paper thus treated was dried at 800C for 3 seconds to obtain a heat-sensitive recording layer of 2 [L in thickness. Then, a clear coating liquid composed of an aqueous dispersion of an acrylic resin (composed mainly 10 of methyl methacrylate units, 2-ethylhexyl acrylate units and styrene units, and having a glass transition point of about 400C) was applied on the coated surface of the aluminized paper to a thickness of 8 pL by the use of a roll coater and dried at 80*C for 10 seconds 15 to obtain metallized paper for laser marking according to the present invention. The metallized paper was irradiated with laser beams from a carbon dioxide laser. A clear mark could be obtained and the color developability was 20 good. A plasticizer resistance test was carried out by holding the metallized paper between wrap films, to find that the plasticizer resistance was so good that no fading of print portion was caused. The results obtained are summarized in Table 9. 25 Example 122 A urea-urethane compound was synthesized in the same manner as in Example 85, and a dispersion was 338 prepared by dispersing 2 g of this compound by grinding it together with 8 g of a 2.5 wt% poly(vinyl alcohol) aqueous solution in a paint shaker for 6 hours. Then, metallized paper for laser marking was 5 produced in the same manner as in Example 121 except for using the dispersion of the aforesaid compound in place of the dispersion of the compound obtained in Example 121, and using diphenyl sulfone in place of aluminum hydroxide, and was evaluated. The results 10 obtained are summarized in Table 9. Comparative Example 24 Metallized paper for laser marking was produced in the same manner as in Example 121 except for using 2
,
2 -bis(4-hydroxyphenyl)propane in place of 15 the urea-urethane compound synthesized in Example 121, and was evaluated. The results obtained are summarized in Table 9. <Color development sensitivity> An article for laser marking was irradiated 20 with laser beams in a dose of 0.6 J/cm 2 from a carbon dioxide laser (Unimark, mfd. by USHIO INC.) through a stencil capable of permitting appearance of figures. When a clear mark was obtained and the coloring density was high, the color development sensitivity was rated 25 good.
339 <Pasticizer resistance.> Three vinyl chloride wrap films were placed on each of the top and under surfaces of the marked article for laser marking, and the resulting assembly 5 was allowed to stand under a load of 300 kg/cm 2 at 40*C for 24 hours. After the standing, the color density of print portion was visually estimated. When there was only a slight decrease in print density, the print preservability was rated good. Table 9 Plasticizer Marking resistance Total sensitivity (print preserv- evaluation ability) Example 121 @ @ @ Example 122 O-@ @ @ Comparative O x Example 24 10 1. Marking sensitivity @ ~- Good color developability. A clear mark can be obtained. o - Somewhat insufficient color development without a problem about visibility. 15 X - Low color developability and unclear print. 2. Plasticizer resistance (print preservability) @ © Substantially no fading. o - A slight color tone change without blur and the like. 20 X - Complete loss of the color of print.
340 Example 123 (1) Production of upper paper A solution prepared by dissolving 2.5 parts by weight of 3-diethylamino-7-chlorofluoran in 80 parts 5 by weight of NISSEKI HISOL N-296 (an oil, a trade name, mfd. by Nippon Sekiyu Kagaku K.K.) was emulsified in 100 parts by weight of a 5% aqueous solution of pH 4.0 prepared by dissolving a styrene-maleic anhydride copolymer together with a small amount of sodium 10 hydroxide. On the other hand, when a mixture of 10 parts by weight of melamine, 25 parts by weight of a 37% aqueous formaldehyde solution and 65 parts by weight of water was adjusted to pH 9.0 with sodium hydroxide and heated at 60*C, the mixture became 15 transparent after 15 minutes and a melamine formaldehyde precondensate was obtained. The precondensate was added to the emulsion obtained above, and the resulting mixture was continuously stirred for 4 hours while maintaining the mixture at 60*C, and then 20 was cooled to room temperature. The solid content of the resulting microcapsule dispersion was 45%. The thus obtained microcapsule dispersion was applied on paper and dried to obtain upper paper. (2) Production of under paper 25 A dispersion was prepared by dispersing 15 g of a composition synthesized in the same manner as in Example 7, by grinding it together with 45 g of a 2 wt% poly(vinyl alcohol) aqueous solution in a paint shaker 341 at ambient temperature for 45 minutes. Another dispersion was prepared by mixing 60 g of calcium carbonate with 90 g of water and stirring the mixture by the use of a stirrer. 5 A coating liquid was prepared by mixing and stirring 40 parts by weight of the dispersion of the aforesaid composition, 125 parts by weight of the calcium carbonate dispersion and 120 parts by weight of a 10 wt% poly(vinyl alcohol) aqueous solution. 10 The coating liquid was applied on base paper with a basis weight of 40 g/m 2 by the use of a bar coater of rod number 10 to obtain under paper. The result of color density evaluation was so good that the optical density was 0.7. 15 The result of evaluating the solvent resist ance by the use of hand cream was so good that reading of a print portion was possible. The results obtained are summarized in Table 10. Comparative Example 25 20 A pressure-sensitive recording material was produced in the same manner as in Example 123 except for using activated clay as developer in place of the urea-urethane compound used in Example 123, and was evaluated. The results obtained are summarized in 25 Table 10.
342 Table 10 Coloring density of Solvent resistance pressure-sensitive (hand cream) paper Example 123 1.3 @ Comparative 0. 9 Example 25 1. Coloring density becomes higher with an increase of optical density (OD value). 2. Solvent resistance (hand cream) @ ~ Substantially no fading. 5 0 - A slight color tone change without blur and the like. A - Marked fading. X ~ Complete loss of the color of print. INDUSTRIAL APPLICABILITY 10 Employment of a specific urea-urethane compound makes it possible to provide at a low price a color-producing composition and a recording material which are excellent in image preservability and color development sensitivity.
Claims (89)
1. A urea-urethane compound characterized by being represented by the following formula (c) and having a molecular weight of 5,000 or less: 0 0 C c (c) R-0 N-A 1 -N N-A 2 H H H wherein R is an aliphatic compound residue, A, and A 2 are independently an aromatic compound residue, the nitrogen atoms of the urea group are directly bonded to the carbon atoms, respectively, of the aromatic rings of A, and A 2 , and R, A and A 2 may have one or more substituents.
2. A urea-urethane compound characterized by being represented by the following formula (d): 0 0 / ~ N.(d) R-0 N N H U JH H wherein R is an aliphatic compound residue, hydrogen atom(s) of each benzene ring may be replaced by an aromatic compound residue, an aliphatic compound residue, a heterocyclic compound residue, a hydroxyl group, a nitro group, a nitrile group, a carbamoyl group, a sulfamoyl group, a carboxyl group, a nitroso group, an amino group, an oxyamino group, a nitroamino group, a hydrazino group, a ureido group, an isocyanate group, a mercapto group, a sulfo group or a halogen 344 atom, and R may have one or more substituents.
3. A urea-urethane compound characterized by being represented by the following formula (e) or (f), having at least one urethane group and at least one urea group in a total number of not more than 10 and not less than 3, and having a molecular weight of 5,000 or less: 0 0 (e) R-O N--Y-N N--a1 H H H - - n wherein R is an aliphatic compound residue, Y is an aromatic compound residue, a heterocyclic compound residue or an aliphatic compound residue, a, is an aromatic, heterocyclic or aliphatic compound residue which is different from Y and has a valence of 2 or more, n is an integer of 2 or more, and each of the residues may have one or more substituents; or 0 0 C c 0 N-Y-N N-Z1 H H H wherein Z, and Y are independently an aromatic compound residue or a heterocyclic compound residue, P, is an aliphatic compound residue having a valence of 2 or more, n is an integer of 2 or more, and each of the residues may have one or more substituents.
4. A urea-urethane compound characterized by 345 being represented by the following formula (g) or (h): 0 0 Il II C (g) P1-0 N N H H H _n wherein hydrogen atom(s) of each benzene ring may be replaced by an aromatic compound residue, an aliphatic compound residue, a heterocyclic compound residue, a hydroxyl group, a nitro group, a nitrile group, a carbamoyl group, a sulfamoyl group, a carboxyl group, a nitroso group, an amino group, an oxyamino group, a nitroamino group, a hydrazino group, a ureido group, an isocyanate group, a mercapto group, a sulfo group or a halogen atom, 0i is an aliphatic compound residue having a valence of 2 or more, n is an integer of 2 or more, and each of the residues may have one or more substituents; or 0 0 0 0 R ---- -- i / \-- -N -- N/&O R (h) H H H kro- H HK H wherein Rs are independently an aliphatic compound residue, hydrogen atom(s) of each benzene ring may be replaced by an aromatic compound residue, an aliphatic compound residue or a heterocyclic compound residue, each of the residues may have one or more substituents, Yi is a group selected from the group consisting of -SO 2 -, -0-, - (S) n-, - (CH 2 ) n-, -CO-, -CONH-, -NH-, -CH(COOR 1 )-, -C(CF 3 ) 2 -, -CR 2 R 3 - and any of groups 346 represented by the formulas (a): O O CH 3 ---O -0 CH 3 CH 3 CH 3 -C - O O- (a) I Ij CH 3 CH 3 00--O - -O QO 0 or is absent, each of R 1 , R 2 and R 3 is an alkyl group, and n is 1 or 2.
5. A urea-urethane composition which is characterized by comprising a urea-urethane compound and a diluent.
6. A urea-urethane composition according to 347 claim 5, wherein the diluent is a urea compound and/or a urethane compound.
7. A urea-urethane composition according to claim 5, wherein the diluent is a compound obtained by reacting a polyisocyanate compound with a hydroxy compound or an amino compound.
8. A urea-urethane composition obtained by reacting a polyisocyanate compound with a hydroxy compound and an amino compound, which is characterized by comprising 50 wt% or more of a urea-urethane compound having at least one urea group and at least one urethane group in a total number of 2 to 10 in the molecular structure and having a molecular weight of 5,000 or less.
9. A urea-urethane composition according to claim 8, wherein the hydroxy compound is a phenolic compound.
10. A urea-urethane composition according to claim 8, wherein the hydroxy compound is an alcohol compound.
11. A urea-urethane composition according to any one of claims 8 to 10, wherein the amino compound is an aromatic amino compound.
12. - A urea-urethane composition according to any one of claims 8 to 11, wherein the polyisocyanate compound is an aromatic polyisocyanate compound.
13. A process for producing a urea-urethane composition, characterized by reacting a polyisocyanate 348 compound with a hydroxy compound so that the ratio of the number of moles of the polyisocyanate compound to the number of hydroxyl equivalents of the hydroxy compound becomes 100/1 to 1/2, to form one or more urethane groups from some of the isocyanate groups of the polyisocyanate compound, and then adding an amino compound thereto to react the same with the remaining isocyanate group(s) of the polyisocyanate compound to form one or more urea groups.
14. A process for producing a urea-urethane composition, characterized by reacting a polyisocyanate compound with an amino compound so that the ratio of the number of moles of the polyisocyanate compound to the number of amino equivalents of the amino compound becomes 100/1 to 1/2, to form one or more urea groups from some of the isocyanate groups of the polyiso cyanate compound, and then adding a hydroxy compound thereto to react the same with the remaining isocyanate group(s) of the polyisocyanate compound to form one or more urethane groups.
15. A process for producing a urea-urethane composition according to claim 13 or 14, characterized by successively carrying out the reaction for forming one or more urethane groups and the reaction for form ing one or more urea groups.
16. A process for producing a urea-urethane composition which comprises reacting an amino compound with a polyisocyanate adduct obtained by the reaction 349 of a polyisocyanate compound with a hydroxy compound, so that the equivalent ratio of isocyanate group to amino group becomes 2/1 to 1/100, to form one or more urea groups, and then removing the unreacted amino compound.
17. A process for producing a urea-urethane composition which comprises reacting a hydroxy compound with a polyisocyanate adduct obtained by the reaction of a polyisocyanate compound with an amino compound, so that the equivalent ratio of isocyanate group to hydroxyl group becomes 2/1 to 1/100, to form one or more urethane groups, and then removing the unreacted hydroxy compound.
18. A process for producing a urea-urethane composition according to any one of claims 13 to 17, characterized by carrying out the reaction for forming one or more urethane groups and/or the reaction for forming one or more urea groups, without a solvent, or carrying out the reaction for forming one or more urethane groups and the reaction for forming one or more urea groups, by the use of the same solvent.
19. A process for producing a urea-urethane composition according to any one of claims 13 to 18, wherein the reaction for forming one or more urethane groups and/or the reaction for forming one or more urea groups are carried out at a temperature of 0 - 300 0 C.
20. A process for producing a urea-urethane composition according to any one of claims 13 to 19, 350 wherein the reaction for forming one or more urethane groups and/or the reaction for forming one or more urea groups are carried out in the presence of a catalyst.
21. A color-producing composition comprising a developer comprising a urea-urethane compound.
22. A color-producing composition comprising a developer comprising a urea-urethane compound, and a colorless or light-colored dye precursor.
23. A color-producing composition according to claim 22, wherein the colorless or light-colored dye precursor is a leuco dye.
24. A color-producing composition according to claims 21 to 23, wherein said developer is a urea urethane compound according to any one of claims 1 to 4, a urea-urethane composition according to any one of claims 5 to 12, or a composition produced by a produc tion process according to any one of claims 13 to 20.
25. A color-producing composition according to either of claims 23 and 24, characterized in that the leuco dye is at least one leuco dye selected from triarylmethane type leuco dyes, fluoran type leuco dyes, fluorene type leuco dyes and diphenylmethane type leuco dyes.
26. A color-producing composition according to either of claims 23 and 24, characterized in that the leuco dye is a compound represented by the following formula (i): 351 Y2 Y3--N O y 4 Y C=O N-Od(i) IH Y6 C=O wherein both Y 2 and Y 3 are alkyl groups or alkoxyalkyl groups, Y 4 is a hydrogen atom, an alkyl group or an alkoxy group, and each of Y 5 and Y. is a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group.
27. A color-producing composition according to either of claims 23 and 24, characterized in that the leuco dye is a compound represented by the following formula (j): R 6 R 5 0 R7 C=0 (j) R0 R10 R9 wherein each of R. and RE is a group represented by the formula (k) or the formula (1): R11 R15 (k) R12 R14 R13 352 (wherein each of R 11 through R 15 is a hydrogen atom, a halogen atom, a C 1 -C 8 alkyl group, a C1-Ce alkoxy group, or -NR 16 R,, wherein each of R 16 and R 1 , is an alkyl group of 1 to 8 carbon atoms), or R18 N Q R 19 (1) (wherein each of R 1 and R 19 is a hydrogen atom, an alkyl group of 1 to 8 carbon atoms, or a phenyl group), and each of R, through R 10 is a hydrogen atom, a halogen atom, an alkyl group of 1 to 8 carbon atoms, an alkoxy group of 1 to 8 carbon atoms, or -NR 20 R 2 1 wherein each of R 20 and R 21 is an alkyl group of 1 to 8 carbon atoms.
28. A color-producing composition according to any one of claims 21 to 27, characterized in that the melting point of the urea-urethane compound developer is not higher than 500*C and not lower than 40'C.
29. A color-producing composition according to any one of claims 21 to 27, characterized in that the urea-urethane compound developer comprises a compound selected from compounds represented by the following general formula (V) or (VI): - .~ ~ 6 - N - ~ N ~ N - ~ O § N ] (V ) 1I H4 ijH HK, 7 H HK H wherein hydrogen atom(s) of each benzene ring may be replaced by an aromatic compound residue, an aliphatic 353 compound residue, a heterocyclic compound residue, a nitro group, a hydroxyl group, a carboxyl group, a nitroso group, a nitrile group, a carbamoyl group, a ureido group, an isocyanate group, a mercapto group, a sulfo group, a sulfamoyl group or a halogen atom, each of the residues may have one or more substituents, y is a group selected from the group consisting of -SO 2 -, -0-, -(S) -, -(CH 2 )n-, -CO-, -CONH- and any of groups represented by the formulas (a): 354 CH 3 OH 3 CH 3 CH 3 -0 0- (a) H 3 -H 3 -0--O- 0 11 or is absent, and n is 1 or 2; and -H H( V I) wherein hydrogen atom(s) of each benzene ring may be replaced by an aromatic compound residue, an aliphatic compound residue, a heterocyclic compound residue, a 355 hydroxyl group, a nitro group, a nitrile group, a carbamoyl group, a sulfamoyl group, a carboxyl group, a nitroso group, an amino group, an oxyamino group, a nitroamino group, a hydrazino group, a ureido group, an isocyanate group, a mercapto group, a sulfo group or a halogen atom, each of the residues may have one or more substituents, 5 is a group selected from the group consisting of -SO 2 -, -0-, -(S) .-, -(CH 2 ) n-, -CO-, -CONH-, -NH-, -CH (COOR1) -, -C (CF 3 ) 2 - and -CR 2 R 3 - or is absent, each of R 1 , R 2 and R 3 is an alkyl group, and n is 1 or 2.
30. A color-producing composition according to any one of claims 21 to 27, characterized in that the urea-urethane compound developer comprises a compound selected from compounds represented by the following structural formulas (XX) and (XXI): H3C NC-N S NCN CH3 O NH HN. 0 C C' 0 0 (XX) (XXI) CH 3 0H 3 0 H 3 C o- 0 o-ci Q9 NH HN. O NH b 00 356
31.~ A color-producing composition according to any one of claims 21 to 30, which further comprises a heat-meltable material.
32. A color-producing composition according to claim 31, characterized in that the heat-meltable material is at least one compound selected from 0 naphthylbenzyl ether, p-benzylbiphenyl, 1,2-di(m methylphenoxy)ethane, di-p-methylbenzyl oxalate, 1,2 diphenoxymethylbenzene, m-terphenyl and stearamide.
33. A color-producing composition according to claim 31, wherein the heat-meltable material is that represented by the following structural formula (XVIII): 0- Y - 0 (X V I I I )-C wherein Y is any of -SO 2 -, -(S)n-, -0-, -CO-, -CH 2 -, -CH (C 6 H 5 ) -, -C (CH 3 ) 2-1 -COCO-, -C0 3 -, -COCH 2 CO-, -COOCH 2 -, -CONH-, -OCH 2 - and -NH-, n is 1 or 2, and hydrogen atom(s) of each benzene ring may be replaced by a halogen atom, a hydroxyl group, a nitro group, a nitroso group, a nitrile group, an isocyanate group, an isothiocyanate group, a mercapto group, a sulfamoyl group, a sulfonic acid group, an amino group, an aromatic compound residue, an aliphatic compound residue or a heterocyclic compound residue.
34. A color-producing composition according to claim 33, wherein the heat-meltable material is that represented by the following structural formula (XIX): 357 0 0*-0 (XIX) OiO 0 wherein hydrogen atom(s) of each benzene ring may be replaced by a halogen atom, a hydroxyl group, a nitro group, a nitroso group, a nitrile group, an isocyanate group, an isothiocyanate group, a mercapto group, a sulfamoyl group, a sulfonic acid group, an amino group, an aromatic compound residue, an aliphatic compound residue or a heterocyclic compound residue.
35. A color-producing composition according to any one of claims 21 to 34, which further comprises an isocyanate compound.
36. A color-producing composition according to any one of claims 21 to 34, which further comprises an isocyanate compound and an imino compound.
37. A color-producing composition according to any one of claims 21 to 36, which further comprises an amino compound.
38. A color-producing composition according to any one of claims 21 to 37, wherein the developer further comprises an acidic developer.
39. A color-producing composition according to claim 38, characterized in that the acidic developer is at least one developer selected from 2,2-bis(4-hydroxy phenyl)propane, 4-isopropyloxyphenyl-4'-hydroxyphenyl sulfone, bis(3-ally-4-hydroxyphenyl)sulfone, 2,4' dihydroxydiphenylsulfone and 4,4'-[oxybis(ethyleneoxy- 358 p-phenylenesulfonyl)]diphenol.
40. A color-producing composition according to any one of claims 21 to 39, which further comprises a fluorescent dye.
41. A color-producing composition according to any one of claims 21 to 40, which further comprises a shelf-stability-imparting agent.
42. A recording material comprising a substrate and a color-producing layer formed thereon, said color producing layer comprising a urea-urethane compound according to any one of claims 1 to 4, a urea-urethane composition according to any one of claims 5 to 12, or a color-producing composition according to any one of claims 21 to 41.
43. A recording material according to claim 42, characterized in that a protective layer for the color producing layer is formed on the color-producing layer.
44. A recording material according to claim 43, characterized in that the protective layer comprises a water-soluble polymer.
45. A recording material according to either of claims 43 and 44, characterized in that the protective layer comprises an inorganic pigment and/or an organic pigment.
46. A recording material according to any one of claims 43 to 45, characterized in that the protective layer comprises a lubricant.
47. A recording material according to claim 42, 359 characterized in that an intermediate layer is formed on the substrate and that the color-producing layer is formed on said intermediate layer.
48. A recording material according to claim 47, characterized in that the intermediate layer comprises a water-soluble polymer.
49. A recording material according to either of claims 47 and 48, characterized in that the inter mediate layer comprises an inorganic pigment and/or an organic pigment.
50. A recording material according to claim 42, characterized in that a back coating layer is formed on the substrate on the side reverse to the side having the color-producing layer formed thereon.
51. A recording material according to claim 50, characterized in that the back coating layer comprises a water-soluble polymer.
52. A recording material according to either of claims 50 and 51, characterized in that the back coating layer comprises an inorganic pigment and/or an organic pigment.
53. A recording material according to any one of claims 42 to 52, characterized by using at least one compound selected from water-soluble polymers and anionic surfactants, as a dispersing agent for the urea-urethane compound.
54. A recording material according to any one of claims 42 to 52, characterized by using at least one 360 compound selected from poly(vinyl alcohol)s, modified poly(vinyl alcohol)s, methyl cellulose, hydroxypropyl methyl cellulose, condensed sodium naphthalene sulfonate, polycarboxylic acid ammonium salts, water soluble low-molecular weight copolymers, and sodium 2 ethylhexylsulfosuccinate, as a dispersing agent for the urea-urethane compound.
55. A recording material according to any one of claims 42 to 54, characterized by using at least one compound selected from water-soluble polymers, nonionic surfactants and anionic surfactants, as a dispersing agent for a dye precursor.
56. A recording material according to any one of claims 42 to 54, characterized by using at least one compound selected from methyl cellulose, hydroxy propylmethyl cellulose, polyethylene glycol fatty acid esters, polyoxyethylene alkyl ether sulfates and sodium 2 -ethylhexylsulfosuccinate, as a dispersing agent for a dye precursor.
57. A recording material according to any one of claims 42 to 56, which is a heat-sensitive recording material.
58. A heat-sensitive recording material according to claim 57, characterized in that the average particle size of the urea-urethane compound is not more than 5 pm and not less than 0.05 pm.
59. A heat-sensitive recording material according to claims 57 and 58, characterized in that a liquid 361 temperature at grinding of the urea-urethane compound is 60*C or lower.
60. A heat-sensitive recording material according to any one of claims 57 to 59, characterized in that a pH at grinding of the urea-urethane compound is 5 to 10.
61. A heat-sensitive recording material according to any one of claims 57 to 60, characterized by using at least one compound selected from water-soluble polymers and anionic surfactants, as a dispersing agent for a heat-meltable material.
62. A heat-sensitive recording material according to any one of claims 57 to 60, characterized by using at least one compound selected from poly(vinyl alcohol)s, modified poly(vinyl alcohol)s,'methyl cellulose, hydroxypropylmethyl cellulose, condensed sodium naphthalenesulfonate, polycarboxylic acid ammonium salts, water-soluble low-molecular weight copolymers, and sodium 2-ethylhexylsulfosuccinate, as a dispersing agent for a heat-meltable material.
63. A heat-sensitive recording material according to any one of claims 57 to 62, characterized in that the urea-urethane compound and a heat-meltable material are finely ground together.
64. A heat-sensitive recording material according to any one of claims 57 to 63, characterized in that the pH of the substrate surface to be coated with the heat-sensitive recording layer of the heat-sensitive 362 recording material is 3 to 9.
65. A process for producing a heat-sensitive recording material according to any one of claims 57 to 64, characterized by applying on the substrate a heat sensitive coating liquid of pH 5 to 12 for forming the heat-sensitive recording layer of the heat-sensitive recording material.
66. A recording material according to claim 42, which is a heat-sensitive magnetic recording material.
67. A heat-sensitive magnetic recording material according to claim 66, characterized in that a heat sensitive recording layer comprising a urea-urethane compound developer is formed on one side of the substrate, and a magnetic recording layer on the other side.
68. A railroad ticket that is a heat-sensitive magnetic recording material according to claim 66 or 67.
69. A ticket that is a heat-sensitive magnetic recording material according to claim 66 or 67.
70. A recording material according to claim 42, which is a label for heat-sensitive recording.
71. A label for heat-sensitive recording accord ing to claim 70, characterized in that a heat-sensitive recording layer comprising a urea-urethane compound developer is formed on one side of the substrate, and an adhesive layer on the other side.
72. A label for heat-sensitive recording 363 according to claim 71, characterized in that a back coating layer is formed between the adhesive layer and the substrate.
73. A label for heat-sensitive recording according to either of claims 71 and 72, characterized in that an intermediate layer is formed between the heat-sensitive recording layer and the substrate.
74. A label for heat-sensitive recording according to any one of claims 71 to 73, characterized in that a protective layer is formed on the heat sensitive recording layer.
75. A recording material according to claim 42, which is a multicolor heat-sensitive recording material.
76. A multicolor heat-sensitive recording material according to claim 75, wherein at least two heat-sensitive recording layers are formed on one side of the substrate, said recording material being characterized in that at least one of said heat sensitive recording layers comprises a urea-urethane compound developer.
77. A multicolor heat-sensitive recording material according to claim 76, characterized in that an intermediate layer is formed between the heat sensitive recording layers.
78. A multicolor heat-sensitive recording material characterized by comprising a substrate and two heat-sensitive recording layers laminated on one F W 364 side of the substrate which have different color development temperatures, respectively, and undergo color development in different color tones, respec tively, the upper heat-sensitive recording layer comprising either an agent used both as developer and tone reducer, or a reversible developer, and the lower heat-sensitive recording layer comprising a urea urethane compound developer.
79. A multicolor heat-sensitive recording material according to claim 78, characterized in that, of the two heat-sensitive recording layers, the upper layer is a low-temperature color-producing layer capable of undergoing color development at a low temperature and undergoing achromatization at a high temperature, and the lower layer is a high-temperature color-producing layer capable of undergoing color development at a high temperature.
80. An article for laser marking characterized by having on the surface a heat-sensitive recording layer comprising a urea-urethane compound developer.
81. An article for laser marking characterized by having on the surface a heat-sensitive recording layer comprising a colorless or light-colored dye precursor, a urea-urethane compound developer and a recording sensitivity improving agent.
82. An article for laser marking according to either of claims 80 and 81, characterized by having on the heat-sensitive recording layer a protective layer 365 comprising an aqueous binder having a glass transition point of 20 - 800C.
83. An article for laser marking according to claim 81, wherein the recording sensitivity improving agent is at least one compound selected from aluminum hydroxide, muscovite, wollastonite and kaolin.
84. An article for laser marking according to any one of claims 80 to 83, which is any of labels, packag ing materials and containers.
85. A process for producing an article for laser marking, characterized by applying on a substrate a color-producing marking composition comprising a urea urethane compound developer, and drying the thus treated substrate.
86. A process for producing an article for laser marking, characterized by applying on a substrate a color-producing marking composition comprising a colorless or light-colored dye precursor, a urea urethane compound developer and a recording sensitivity improving agent, and drying the thus treated substrate.
87. A method for marking an article, character ized by irradiating the heat-sensitive recording layer of an article for laser marking according to any one of claims 80 to 84, with laser beams.
88. A color-producing marking composition characterized by comprising a urea-urethane compound developer.
89. A color-producing marking composition 366 characterized by comprising a colorless or light colored dye precursor, a urea-urethane compound developer and a recording sensitivity improving agent.
Applications Claiming Priority (31)
Application Number | Priority Date | Filing Date | Title |
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JP2000057538 | 2000-03-02 | ||
JP2000-57693 | 2000-03-02 | ||
JP2000057693 | 2000-03-02 | ||
JP2000-57538 | 2000-03-02 | ||
JP2000058249 | 2000-03-03 | ||
JP2000059216A JP2001246849A (en) | 2000-03-03 | 2000-03-03 | New color former and heat sensitive recording material |
JP2000-58249 | 2000-03-03 | ||
JP2000-58279 | 2000-03-03 | ||
JP2000058823A JP2001246858A (en) | 2000-03-03 | 2000-03-03 | Heat-sensitive magnetic recording material |
JP2000058770A JP2001246857A (en) | 2000-03-03 | 2000-03-03 | Multicolor heat-sensitive recording material |
JP2000058861A JP2001246859A (en) | 2000-03-03 | 2000-03-03 | Heat-sensitive recording label |
JP2000058279A JP2001246854A (en) | 2000-03-03 | 2000-03-03 | Recording material |
JP2000059298 | 2000-03-03 | ||
JP2000-58468 | 2000-03-03 | ||
JP2000-59216 | 2000-03-03 | ||
JP2000058594A JP2001246856A (en) | 2000-03-03 | 2000-03-03 | Heat-sensitive recording sheet |
JP2000059047 | 2000-03-03 | ||
JP2000-58861 | 2000-03-03 | ||
JP2000-59298 | 2000-03-03 | ||
JP2000-58770 | 2000-03-03 | ||
JP2000058891A JP2001246860A (en) | 2000-03-03 | 2000-03-03 | Coloring marking agent, marking method and marking article |
JP2000-58823 | 2000-03-03 | ||
JP2000-59047 | 2000-03-03 | ||
JP2000058468A JP2001246855A (en) | 2000-03-03 | 2000-03-03 | Recording sheet |
JP2000-58891 | 2000-03-03 | ||
JP2000-58594 | 2000-03-03 | ||
JP2000-267302 | 2000-09-04 | ||
JP2000-267467 | 2000-09-04 | ||
JP2000267467A JP4577965B2 (en) | 2000-03-03 | 2000-09-04 | Thermal recording material and method for producing the same |
JP2000267302 | 2000-09-04 | ||
PCT/JP2001/001577 WO2001066515A1 (en) | 2000-03-02 | 2001-03-01 | Novel color former and recording material |
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AU3602901A true AU3602901A (en) | 2001-09-17 |
AU779924B2 AU779924B2 (en) | 2005-02-17 |
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KR (1) | KR100549037B1 (en) |
CN (1) | CN1303064C (en) |
AU (1) | AU779924B2 (en) |
CA (1) | CA2399054A1 (en) |
WO (1) | WO2001066515A1 (en) |
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CN102775810B (en) * | 2012-07-23 | 2014-12-03 | 烟台大学 | Fluorane color former and preparation method thereof |
US9126451B2 (en) * | 2013-12-18 | 2015-09-08 | Appvion, Inc. | Thermal recording materials |
BR112019003249B1 (en) | 2016-08-24 | 2022-10-18 | Nippon Soda Co., Ltd | MATERIAL AND REGISTRATION SHEET |
DE102018111224B4 (en) * | 2018-05-09 | 2020-12-10 | Papierfabrik August Koehler Se | Thermosensitive recording material |
WO2020117255A1 (en) * | 2018-12-06 | 2020-06-11 | Hewlett-Packard Development Company, L.P. | Imaging media |
JP2020132986A (en) * | 2019-02-25 | 2020-08-31 | 東京エレクトロン株式会社 | Composition for film deposition and film deposition method |
CN114890917A (en) * | 2022-05-25 | 2022-08-12 | 沈阳感光化工研究院有限公司 | Asymmetric branched non-phenolic color developing agent and synthesis method thereof |
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JPS452594B1 (en) * | 1966-11-28 | 1970-01-28 | ||
DE3100355A1 (en) * | 1981-01-08 | 1982-08-05 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING S-TRIAZINE UNITS AND COMPOUNDS WITH EPOXY GROUPS AND THE USE THEREOF AS BUILT-IN FILLERS IN THE PRODUCTION OF POLYURETHANE PLASTICS |
US4566981A (en) * | 1984-03-30 | 1986-01-28 | Minnesota Mining And Manufacturing Company | Fluorochemicals and fibrous substrates treated therewith: compositions of cationic and non-ionic fluorochemicals |
JPS6135444A (en) * | 1984-07-28 | 1986-02-19 | Konishiroku Photo Ind Co Ltd | Silver halide color photographic sensitive material |
DE58906333D1 (en) * | 1988-04-14 | 1994-01-20 | Ciba Geigy | Disperse dyes. |
EP0449975B1 (en) * | 1988-12-21 | 1997-04-23 | Battelle Memorial Institute | Non-tin-based, low toxicity anti-fouling agents |
WO1992020747A1 (en) * | 1991-05-17 | 1992-11-26 | Battelle Memorial Institute | Marine compositions bearing preferentially concentrated domains of non-tin, organo anti-fouling agents |
US5780483A (en) * | 1995-02-17 | 1998-07-14 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
JPH08311357A (en) * | 1995-05-17 | 1996-11-26 | Fuji Photo Film Co Ltd | Indolylazaphthalide compound and recording material using the compound |
DE69706260T2 (en) * | 1996-04-04 | 2002-06-13 | Oji Paper Co., Ltd. | REVERSIBLE HEAT-SENSITIVE RECORDING MATERIAL |
JPH10310633A (en) * | 1997-05-14 | 1998-11-24 | Nippon Soda Co Ltd | Stabilizer for cationic curing catalyst |
DE19816362A1 (en) * | 1998-04-03 | 1999-10-07 | Grace Gmbh | Matting agent based on coated silicon dioxide |
ATE457976T1 (en) * | 1998-09-04 | 2010-03-15 | Chemipro Kasei Kaisha Ltd | COLOR DEVELOPING COMPOUND AND RECORDING MATERIAL |
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- 2001-03-01 CN CNB018058116A patent/CN1303064C/en not_active Expired - Lifetime
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- 2001-03-01 CA CA002399054A patent/CA2399054A1/en not_active Abandoned
- 2001-03-01 KR KR1020027011356A patent/KR100549037B1/en active IP Right Grant
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KR100549037B1 (en) | 2006-02-02 |
CN1303064C (en) | 2007-03-07 |
CA2399054A1 (en) | 2001-09-13 |
WO2001066515A1 (en) | 2001-09-13 |
CN1496346A (en) | 2004-05-12 |
AU779924B2 (en) | 2005-02-17 |
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