JP6917410B2 - N,n’−ジアリール尿素誘導体及びそれを用いた感熱記録材料 - Google Patents
N,n’−ジアリール尿素誘導体及びそれを用いた感熱記録材料 Download PDFInfo
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- JP6917410B2 JP6917410B2 JP2019097706A JP2019097706A JP6917410B2 JP 6917410 B2 JP6917410 B2 JP 6917410B2 JP 2019097706 A JP2019097706 A JP 2019097706A JP 2019097706 A JP2019097706 A JP 2019097706A JP 6917410 B2 JP6917410 B2 JP 6917410B2
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- Prior art keywords
- phenyl
- bis
- ureido
- group
- benzene
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- 229910052757 nitrogen Inorganic materials 0.000 title claims description 56
- 239000000463 material Substances 0.000 title claims description 55
- -1 alicyclic hydrocarbon Chemical class 0.000 claims description 136
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
- 125000000962 organic group Chemical group 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 12
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 12
- 239000000975 dye Substances 0.000 claims description 11
- 239000000981 basic dye Substances 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 4
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 279
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 227
- 150000007945 N-acyl ureas Chemical class 0.000 description 99
- 230000015572 biosynthetic process Effects 0.000 description 58
- 238000003786 synthesis reaction Methods 0.000 description 58
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 53
- 239000010410 layer Substances 0.000 description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 35
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 238000000576 coating method Methods 0.000 description 23
- 239000000243 solution Substances 0.000 description 21
- 239000011248 coating agent Substances 0.000 description 20
- 229920005989 resin Polymers 0.000 description 20
- 239000011347 resin Substances 0.000 description 20
- 229920002451 polyvinyl alcohol Polymers 0.000 description 19
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 19
- 239000004372 Polyvinyl alcohol Substances 0.000 description 17
- 239000011230 binding agent Substances 0.000 description 16
- 238000002329 infrared spectrum Methods 0.000 description 16
- 238000003860 storage Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 14
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 14
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 11
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 11
- 239000000123 paper Substances 0.000 description 11
- 239000000049 pigment Substances 0.000 description 11
- QKMMHCHOLCPWIV-UHFFFAOYSA-N [3-[[4-methyl-3-[[3-(4-methylphenyl)sulfonyloxyphenyl]carbamoylamino]phenyl]carbamoylamino]phenyl] 4-methylbenzenesulfonate Chemical compound CC1=CC=C(C=C1)S(=O)(=O)OC2=CC=CC(=C2)NC(=O)NC3=CC(=C(C=C3)C)NC(=O)NC4=CC(=CC=C4)OS(=O)(=O)C5=CC=C(C=C5)C QKMMHCHOLCPWIV-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000003973 paint Substances 0.000 description 9
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 230000035945 sensitivity Effects 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- 239000001023 inorganic pigment Substances 0.000 description 7
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- UCJDXUDIBPLNQX-UHFFFAOYSA-N [3-[[3-[[3-(4-methylphenyl)sulfonyloxyphenyl]carbamoylamino]phenyl]carbamoylamino]phenyl] 4-methylbenzenesulfonate Chemical compound CC1=CC=C(C=C1)S(=O)(=O)OC2=CC=CC(=C2)NC(=O)NC3=CC(=CC=C3)NC(=O)NC4=CC(=CC=C4)OS(=O)(=O)C5=CC=C(C=C5)C UCJDXUDIBPLNQX-UHFFFAOYSA-N 0.000 description 6
- 239000012752 auxiliary agent Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 229920000126 latex Polymers 0.000 description 6
- 239000004816 latex Substances 0.000 description 6
- 239000012860 organic pigment Substances 0.000 description 6
- 235000019698 starch Nutrition 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 5
- 235000012211 aluminium silicate Nutrition 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 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 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 229920002678 cellulose Polymers 0.000 description 5
- 235000010980 cellulose Nutrition 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 5
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000011241 protective layer Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 4
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 239000010419 fine particle Substances 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000001254 oxidized starch Substances 0.000 description 4
- 235000013808 oxidized starch Nutrition 0.000 description 4
- 239000002985 plastic film Substances 0.000 description 4
- 229920006255 plastic film Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229920003048 styrene butadiene rubber Polymers 0.000 description 4
- KKVMJJXFKMILSZ-AWEZNQCLSA-N (2s)-3-phenyl-2-(phenylcarbamoylamino)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)NC=1C=CC=CC=1)C1=CC=CC=C1 KKVMJJXFKMILSZ-AWEZNQCLSA-N 0.000 description 3
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical class C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 3
- BBQLCKFJEDETJU-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-phenylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1=CC=CC=C1 BBQLCKFJEDETJU-UHFFFAOYSA-N 0.000 description 3
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 3
- 229940018563 3-aminophenol Drugs 0.000 description 3
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 3
- FKZIDBGIZLBDDF-UHFFFAOYSA-N 4-(4-prop-2-enoxyphenyl)sulfonylphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(OCC=C)C=C1 FKZIDBGIZLBDDF-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XYGQXVWSAAKKQS-UHFFFAOYSA-N [3-[6-[[3-(4-methylphenyl)sulfonyloxyphenyl]carbamoylamino]hexylcarbamoylamino]phenyl] 4-methylbenzenesulfonate Chemical compound CC1=CC=C(C=C1)S(=O)(=O)OC2=CC=CC(=C2)NC(=O)NCCCCCCNC(=O)NC3=CC(=CC=C3)OS(=O)(=O)C4=CC=C(C=C4)C XYGQXVWSAAKKQS-UHFFFAOYSA-N 0.000 description 3
- PVDSCVPYCVASKG-UHFFFAOYSA-N [3-[[3-[[[3-(4-methylphenyl)sulfonyloxyphenyl]carbamoylamino]methyl]cyclohexyl]methylcarbamoylamino]phenyl] 4-methylbenzenesulfonate Chemical compound CC1=CC=C(C=C1)S(=O)(=O)OC2=CC=CC(=C2)NC(=O)NCC3CCCC(C3)CNC(=O)NC4=CC(=CC=C4)OS(=O)(=O)C5=CC=C(C=C5)C PVDSCVPYCVASKG-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 3
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- 239000013078 crystal Substances 0.000 description 3
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- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 3
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000000034 method Methods 0.000 description 3
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- 229920000647 polyepoxide Polymers 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 3
- HGWDEINNQMROCA-HNNXBMFYSA-N (2s)-2-[(3-methylphenyl)carbamoylamino]-3-phenylpropanoic acid Chemical compound CC1=CC=CC(NC(=O)N[C@@H](CC=2C=CC=CC=2)C(O)=O)=C1 HGWDEINNQMROCA-HNNXBMFYSA-N 0.000 description 2
- OQOLSESLQNHUPJ-NSHDSACASA-N (2s)-2-[(3-methylphenyl)carbamoylamino]-4-methylsulfanylbutanoic acid Chemical compound CSCC[C@@H](C(O)=O)NC(=O)NC1=CC=CC(C)=C1 OQOLSESLQNHUPJ-NSHDSACASA-N 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- RUTYWCZSEBLPAK-UHFFFAOYSA-N (4-methylphenyl)sulfonylurea Chemical group CC1=CC=C(S(=O)(=O)NC(N)=O)C=C1 RUTYWCZSEBLPAK-UHFFFAOYSA-N 0.000 description 2
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 2
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
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- UIFAEJQCFLEWCF-UHFFFAOYSA-N 1-methyl-4-[2-(4-methylphenoxy)ethoxy]benzene Chemical compound C1=CC(C)=CC=C1OCCOC1=CC=C(C)C=C1 UIFAEJQCFLEWCF-UHFFFAOYSA-N 0.000 description 2
- PVJZBZSCGJAWNG-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonyl chloride Chemical compound CC1=CC(C)=C(S(Cl)(=O)=O)C(C)=C1 PVJZBZSCGJAWNG-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
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- XCSGHNKDXGYELG-UHFFFAOYSA-N 2-phenoxyethoxybenzene Chemical compound C=1C=CC=CC=1OCCOC1=CC=CC=C1 XCSGHNKDXGYELG-UHFFFAOYSA-N 0.000 description 2
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- MRCPLHFCTBSYJQ-UHFFFAOYSA-N [3-(carbamoylamino)phenyl] 4-methylbenzenesulfonate Chemical compound Cc1ccc(cc1)S(=O)(=O)Oc1cccc(NC(N)=O)c1 MRCPLHFCTBSYJQ-UHFFFAOYSA-N 0.000 description 2
- UXUJNYJFNUMBLW-UHFFFAOYSA-N [3-[[3-[[3-(benzenesulfonyloxy)phenyl]carbamoylamino]-4-methylphenyl]carbamoylamino]phenyl] benzenesulfonate Chemical compound CC1=C(C=C(C=C1)NC(=O)NC2=CC(=CC=C2)OS(=O)(=O)C3=CC=CC=C3)NC(=O)NC4=CC(=CC=C4)OS(=O)(=O)C5=CC=CC=C5 UXUJNYJFNUMBLW-UHFFFAOYSA-N 0.000 description 2
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- 125000006239 protecting group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical class CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
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- 239000013053 water resistant agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- YSNBXPSRZKHQQC-UHFFFAOYSA-L zinc;2-carboxy-5-(octoxycarbonylamino)phenolate Chemical compound [Zn+2].CCCCCCCCOC(=O)NC1=CC=C(C([O-])=O)C(O)=C1.CCCCCCCCOC(=O)NC1=CC=C(C([O-])=O)C(O)=C1 YSNBXPSRZKHQQC-UHFFFAOYSA-L 0.000 description 1
Images
Landscapes
- Heat Sensitive Colour Forming Recording (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
更に近年は4,4’−イソプロピリデンジフェノールや4,4’−ビスフェノールスルホンなどは、環境ホルモンや変異原性などの環境衛生上の問題が指摘されているため、これらの問題のない非フェノール系顕色剤が求められているのが実情である。
[1] 下記一般式(1)で表されるN,N’−ジアリール尿素誘導体。
R1は、C1〜C12の飽和若しくは不飽和の脂肪族炭化水素基、C3〜C12の脂環式炭化水素基、C7〜C12のアラルキル基、又は、C6〜C12のアリール基である。
R2はメチル基である。aは0〜2の整数である。nは0又は1である。)
本発明のN,N’−ジアリール尿素誘導体は、下記一般式(1)で表される。
ジメチルシクロヘキサンジイル基、
本発明の一般式(1)で表されるN,N’−ジアリール尿素誘導体は、下記式(3)で示されるアミノフェノール化合物及び下記式(4)で示されるジイソシアナート化合物を反応させた後、式(5)で表されるハロゲン化スルホニル化合物を脱酸剤存在下に作用させることによって容易に得ることができる。
本発明の感熱記録材料は、常温で無色ないし淡色の塩基性染料と、加熱により該塩基性染料と接触して呈色し得る顕色剤とを含有する感熱記録層を支持体上に設けた感熱記録材料であって、前記顕色剤が、前記のN,N’−ジアリール尿素誘導体を含有する。
このように微分散された分散液に、必要により顔料、バインダー、助剤等を混合撹拌することで感熱記録層塗料は調整される。
下塗り層の組成は、目的のより適宜選択すればよいが、一般に、バインダー、顔料などが含まれる。
保護層に用いられるバインダー、顔料、助剤は、上記の感熱記録層で用いられるものを使用される。
2,4−ビス(3−[3−{p−トルエンスルホニルオキシ}フェニル]ウレイド)トルエンの合成(合成例1)
2,4−ビス(3−[3−{ベンゼンスルホニルオキシ}フェニル]ウレイド)トルエンの合成(合成例2)
2,4−ビス(3−[3−{2−メシチレンスルホニルオキシ}フェニル]ウレイド)トルエンの合成(合成例3)
2,6-ビス(3−[4−{p−トルエンスルホニルオキシ}フェニル]ウレイド)トルエンの合成(合成例4)
1,6−ビス(3−[3−{p−トルエンスルホニルオキシ}フェニル]ウレイド)ヘキサンの合成(合成例5)
1,3−ビス(3−[3−{p−トルエンスルホニルオキシ}フェニル]ウレイド)ベンゼンの合成(合成例6)
1,3−ビス([3−{3−(p−トルエンスルホニルオキシ)フェニル}ウレイド]メチル)シクロヘキサンの合成(合成例7)
1,3−ビス([3−{3−(p−トルエンスルホニルオキシ)フェニル}ウレイド]メチル)ベンゼンの合成(合成例8)
プラスチック中空粒子(商品名:ローペイクSN−1055:中空率:55%、固形分26.5%)100部、焼成カオリンの50%分散液100部、スチレン−ブタジエン系ラテックス(商品名:L−1571 固形分48%)25部、酸化澱粉の10%水溶液50部および水20部を混合して、アンダーコート用塗料を作成した。
[感熱記録用塗料の作成]
A液(染料分散液の調製)
3−(N,N−ジブチルアミノ)−6−メチル−7−アニリノフルオラン 10部
10%ポリビニルアルコール水溶液 10部
水 16.7部
2,4−ビス(3−[3−{p−トルエンスルホニルオキシ}フェニル]ウレイド)トルエン(合成例1) 20部
10%ポリビニルアルコール水溶液 20部
水 33.3部
1,2−ビス(m−トリルオキシ)エタン 15部
10%ポリビニルアルコール水溶液 15部
水 25部
A液(染料剤分散液) 36.7部
B液(顕色剤分散液) 73.3部
C液(増感剤分散液) 55.0部
支持体として坪量が53gの上質紙(酸性紙)にアンダーコート用塗料を乾燥後の面積当たりの質量が6g/m2となるように塗布および乾燥し、その後、感熱記録層用塗料を、乾燥後の面積当たりの質量が3.8g/m2になるように塗布乾燥した。
このシートをス−パーカレンダーで平滑度(JISP8155:2010)が900〜1200sになるように処理して感熱記録材料を作成した。
1.感熱記録性試験(発色試験)
作成した感熱記録材料について、感熱記録紙印字試験機(大倉電気社製TH−PMD)を用い、印加エネルギー0.38mJ/dotで印加した。記録部の印字濃度はマクベス反射濃度計RD−914で測定した。これを試験前サンプル(ブランク)トした。
感熱記録性試験で印加エネルギー0.38mJ/dotで記録した感熱記録材料を試験温度40℃、90%RHの環境下に24時間放置した後、試験片の印字部画像濃度と未印字部の濃度をマクベス反射濃度計で測定した。
感熱記録性試験で印加エネルギー0.38mJ/dotで記録した感熱記録材料を試験温度60℃の恒温環境下に24時間放置した後、試験片の印字部画像濃度と未印字部の濃度をマクベス反射濃度計で測定した。
感熱記録性試験で印加エネルギー0.38mJ/dotで記録した感熱記録材料を5000Luxに100時間暴露しその後、画像濃度をマクベス反射濃度計で測定した。
感熱記録性試験で印加エネルギー0.38mJ/dotで記録した感熱記録材料を水中に15時間浸漬しその後、試験片を風乾させ、画像濃度と未印字部をマクベス反射濃度計で測定した。
感熱記録性試験で印加エネルギー0.38mJ/dotで記録した感熱記録材料にサラダオイル中に10分間浸漬しその後、試験片の油をふき取り、画像濃度をマクベス反射濃度計で測定した。
感熱記録性試験で印加エネルギー0.38mJ/dotで記録した感熱記録材料にサラダオイル中に3時間浸漬しその後、試験片の油をふき取り、画像濃度をマクベス反射濃度計で測定した。この実施例による感熱記録材料の各種試験結果は、表1に記載の通りであった。
実施例1のB液の2,4−ビス(3−[3−{p−トルエンスルホニルオキシ}フェニル]ウレイド)トルエン(合成例1)を2,4−ビス(3−[3−{ベンゼンスルホニルオキシ}フェニル]ウレイド)トルエン(合成例2)に代える以外は実施例1と同様の操作をおこなった。
この実施例による感熱記録材料の各種試験結果は、表1に記載の通りであった。
実施例1のB液の2,4−ビス(3−[3−{p−トルエンスルホニルオキシ}フェニル]ウレイド)トルエン(合成例1)を2,4−ビス(3−[3−{2−メシチレンスルホニルオキシ}フェニル]ウレイド)トルエン(合成例3)に代える以外は実施例1と同様の操作をおこなった。
この実施例による感熱記録材料の各種試験結果は、表1に記載の通りであった。
実施例1のB液の2,4−ビス(3−[3−{p−トルエンスルホニルオキシ}フェニル]ウレイド)トルエン(合成例1)を2,6−ビス(3−[4−{p−トルエンスルホニルオキシ}フェニル]ウレイド)トルエン(合成例4)に代える以外は実施例1と同様の操作をおこなった。
この実施例による感熱記録材料の各種試験結果は、表1に記載の通りであった。
実施例1のB液の2,4−ビス(3−[3−{p−トルエンスルホニルオキシ}フェニル]ウレイド)トルエン(合成例1)を1,6−ビス(3−[3−{p−トルエンスルホニルオキシ}フェニル]ウレイド)ヘキサン(合成例5)に代える以外は実施例1と同様の操作をおこなった。
この実施例による感熱記録材料の各種試験結果は、表1に記載の通りであった。
実施例1のB液の2,4−ビス(3−[3−{p−トルエンスルホニルオキシ}フェニル]ウレイド)トルエン(合成例1)を1,3−ビス(3−[3−{p−トルエンスルホニルオキシ}フェニル]ウレイド)ベンゼン(合成例6)に代える以外は実施例1と同様の操作をおこなった。
この実施例による感熱記録材料の各種試験結果は、表1に記載の通りであった。
実施例1のB液の2,4−ビス(3−[3−{p−トルエンスルホニルオキシ}フェニル]ウレイド)トルエン(合成例1)を1,3−ビス([3−{3−(p−トルエンスルホニルオキシ)フェニル}ウレイド]メチル)シクロヘキサン(合成例7)に代える以外は実施例1と同様の操作をおこなった。
実施例1のB液の2,4−ビス(3−[3−{p−トルエンスルホニルオキシ}フェニル]ウレイド)トルエン(合成例1)を1,3−ビス([3−{3−(p−トルエンスルホニルオキシ)フェニル}ウレイド]メチル)ベンゼン(合成例8)に代える以外は実施例1と同様の操作をおこなった。
実施例1のB液の2,4−ビス(3−[3−{p−トルエンスルホニルオキシ}フェニル]ウレイド)トルエン(合成例1)を4,4’−イソプロピリデンジフェノール(ビスフェノールA)に代える以外は実施例1と同様の操作をおこなった。この参照例による感熱記録材料の各種試験結果は、表1に記載の通りであった。
実施例1のB液の2,4−ビス(3−[3−{p−トルエンスルホニルオキシ}フェニル]ウレイド)トルエン (合成例1)を4,4’−ジヒドロキシジフェニルスルホン(ビスフェノールS)に代える以外は実施例1と同様の操作をおこなった。この参照例による感熱記録材料の各種試験結果は、表1に記載の通りであった。
実施例1のB液の2,4−ビス(3−[3−{p−トルエンスルホニルオキシ}フェニル]ウレイド)トルエン(合成例1)を4−アリルオキシ−4’−ヒドロキシジフェニルスルホンに代える以外は実施例1と同様の操作をおこなった。この参照例による感熱記録材料の各種試験結果は、表1に記載の通りであった。
実施例1のB液の2,4−ビス(3−[3−{p−トルエンスルホニルオキシ}フェニル]ウレイド)トルエン (合成例1)を4−ヒドロキシ−4’−イソプロピルオキシ−ジフェニルスルホンに代える以外は実施例1と同様の操作をおこなった。この参照例による感熱記録材料の各種試験結果は、表1に記載の通りであった。
実施例1のB液の2,4−ビス(3−[3−{p−トルエンスルホニルオキシ}フェニル]ウレイド)トルエン(合成例1)をN−3−(p−トルエンスルホニルオキシ)フェニル−N’−(p−トルエンスルホニル)−尿素に代える以外は実施例1と同様の操作をおこなった。この参照例による感熱記録材料の各種試験結果は、表1に記載の通りであった。
実施例1のB液の2,4−ビス(3−[3−{p−トルエンスルホニルオキシ}フェニル]ウレイド)トルエン (合成例1)をN−[2−(3−フェニルウレイド)フェニル]ベンゼンスルホンアミドに代える以外は実施例1と同様の操作をおこなった。この参照例による感熱記録材料の各種試験結果は、表1に記載の通りであった。
Claims (3)
- 下記一般式(1)で表されるN,N’−ジアリール尿素誘導体。
R1は、C1〜C12の飽和若しくは不飽和の脂肪族炭化水素基、C3〜C12の脂環式炭化水素基、C7〜C12のアラルキル基、又は、C6〜C12のアリール基である。
R2はメチル基である。aは0〜2の整数である。nは0又は1である。) - 常温で無色ないし淡色の塩基性染料と、加熱により該染料と接触して呈色し得る顕色剤とを含有する感熱記録層を支持体上に設けた感熱記録材料であって、顕色剤として、請求項1又は2に記載のN,N’−ジアリール尿素誘導体を含有する感熱記録材料。
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