GB2395569A - Heat sensitive compositions comprising benzoic acid derivatives. - Google Patents
Heat sensitive compositions comprising benzoic acid derivatives. Download PDFInfo
- Publication number
- GB2395569A GB2395569A GB0326306A GB0326306A GB2395569A GB 2395569 A GB2395569 A GB 2395569A GB 0326306 A GB0326306 A GB 0326306A GB 0326306 A GB0326306 A GB 0326306A GB 2395569 A GB2395569 A GB 2395569A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- hydroxy
- bis
- heat sensitive
- benzoic acid
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 40
- 150000001558 benzoic acid derivatives Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 239000000463 material Substances 0.000 claims abstract description 30
- 239000003381 stabilizer Substances 0.000 claims abstract description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000003435 aroyl group Chemical group 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
- 231100000489 sensitizer Toxicity 0.000 claims description 15
- 239000000758 substrate Substances 0.000 claims description 8
- 239000006104 solid solution Substances 0.000 claims description 3
- -1 C6-C10aryl Chemical group 0.000 abstract description 78
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 52
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 38
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 38
- 239000006185 dispersion Substances 0.000 description 30
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 30
- 125000003944 tolyl group Chemical group 0.000 description 23
- 239000000123 paper Substances 0.000 description 16
- 239000005711 Benzoic acid Substances 0.000 description 15
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 15
- 235000010233 benzoic acid Nutrition 0.000 description 15
- WPYMKLBDIGXBTP-VQEHIDDOSA-N benzoic acid Chemical compound OC(=O)C1=CC=C[13CH]=C1 WPYMKLBDIGXBTP-VQEHIDDOSA-N 0.000 description 15
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 14
- 239000012964 benzotriazole Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 229920002451 polyvinyl alcohol Polymers 0.000 description 12
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 12
- 229920001577 copolymer Polymers 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000004372 Polyvinyl alcohol Substances 0.000 description 9
- 239000006096 absorbing agent Substances 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- 239000011230 binding agent Substances 0.000 description 8
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 8
- 239000011241 protective layer Substances 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- MGNPLIACIXIYJE-UHFFFAOYSA-N n-fluoroaniline Chemical compound FNC1=CC=CC=C1 MGNPLIACIXIYJE-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000004014 plasticizer Substances 0.000 description 6
- 150000003457 sulfones Chemical class 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 229920002401 polyacrylamide Polymers 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- UWDMKTDPDJCJOP-UHFFFAOYSA-N 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-carboxylate Chemical compound CC1(C)CC(O)(C(O)=O)CC(C)(C)N1 UWDMKTDPDJCJOP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 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
- 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 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 235000012343 cottonseed oil Nutrition 0.000 description 4
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 229960004889 salicylic acid Drugs 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000001856 Ethyl cellulose Substances 0.000 description 3
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 3
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 229910052570 clay Inorganic materials 0.000 description 3
- 239000002385 cottonseed oil Substances 0.000 description 3
- 229920001249 ethyl cellulose Polymers 0.000 description 3
- 235000019325 ethyl cellulose Nutrition 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229920000609 methyl cellulose Polymers 0.000 description 3
- 239000001923 methylcellulose Substances 0.000 description 3
- 235000010981 methylcellulose Nutrition 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- YGLZTWVJZMAGFG-UHFFFAOYSA-N (4-hydroxyphenyl) pentanoate Chemical compound CCCCC(=O)OC1=CC=C(O)C=C1 YGLZTWVJZMAGFG-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
- 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 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 2
- RZTDESRVPFKCBH-UHFFFAOYSA-N 1-methyl-4-(4-methylphenyl)benzene Chemical group C1=CC(C)=CC=C1C1=CC=C(C)C=C1 RZTDESRVPFKCBH-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 2
- CONFUNYOPVYVDC-UHFFFAOYSA-N 3,3-bis(1-ethyl-2-methylindol-3-yl)-2-benzofuran-1-one Chemical compound C1=CC=C2C(C3(C4=CC=CC=C4C(=O)O3)C3=C(C)N(C4=CC=CC=C43)CC)=C(C)N(CC)C2=C1 CONFUNYOPVYVDC-UHFFFAOYSA-N 0.000 description 2
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- IPAJDLMMTVZVPP-UHFFFAOYSA-N Crystal violet lactone Chemical compound C1=CC(N(C)C)=CC=C1C1(C=2C=CC(=CC=2)N(C)C)C2=CC=C(N(C)C)C=C2C(=O)O1 IPAJDLMMTVZVPP-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical class CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 229920000881 Modified starch Polymers 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 150000005130 benzoxazines Chemical class 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
- 235000021240 caseins Nutrition 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 2
- 239000006081 fluorescent whitening agent Substances 0.000 description 2
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- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 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 2
- 150000002596 lactones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 235000019426 modified starch Nutrition 0.000 description 2
- 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 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229960003742 phenol Drugs 0.000 description 2
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
- 239000000088 plastic resin Substances 0.000 description 2
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- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 2
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
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- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 2
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- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
- CSUUDNFYSFENAE-UHFFFAOYSA-N (2-methoxyphenyl)-phenylmethanone Chemical compound COC1=CC=CC=C1C(=O)C1=CC=CC=C1 CSUUDNFYSFENAE-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
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- ARVUDIQYNJVQIW-UHFFFAOYSA-N (4-dodecoxy-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(OCCCCCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 ARVUDIQYNJVQIW-UHFFFAOYSA-N 0.000 description 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- LJSLYKNKVQMIJY-UHFFFAOYSA-N 1,4-diethoxynaphthalene Chemical compound C1=CC=C2C(OCC)=CC=C(OCC)C2=C1 LJSLYKNKVQMIJY-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- RHDYQUZYHZWTCI-UHFFFAOYSA-N 1-methoxy-4-phenylbenzene Chemical group C1=CC(OC)=CC=C1C1=CC=CC=C1 RHDYQUZYHZWTCI-UHFFFAOYSA-N 0.000 description 1
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- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- ZCILODAAHLISPY-UHFFFAOYSA-N biphenyl ether Natural products C1=C(CC=C)C(O)=CC(OC=2C(=CC(CC=C)=CC=2)O)=C1 ZCILODAAHLISPY-UHFFFAOYSA-N 0.000 description 1
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical group OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 1
- GOJOVSYIGHASEI-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) butanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCC(=O)OC1CC(C)(C)NC(C)(C)C1 GOJOVSYIGHASEI-UHFFFAOYSA-N 0.000 description 1
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 1
- SODJJEXAWOSSON-UHFFFAOYSA-N bis(2-hydroxy-4-methoxyphenyl)methanone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1O SODJJEXAWOSSON-UHFFFAOYSA-N 0.000 description 1
- QWHCTYYBLDCYIT-UHFFFAOYSA-N bis[(4-chlorophenyl)methyl] oxalate Chemical compound C1=CC(Cl)=CC=C1COC(=O)C(=O)OCC1=CC=C(Cl)C=C1 QWHCTYYBLDCYIT-UHFFFAOYSA-N 0.000 description 1
- FPFZBTUMXCSRLU-UHFFFAOYSA-N bis[(4-methylphenyl)methyl] oxalate Chemical compound C1=CC(C)=CC=C1COC(=O)C(=O)OCC1=CC=C(C)C=C1 FPFZBTUMXCSRLU-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- OIVQLSUKOZNNCT-UHFFFAOYSA-N dibenzyl benzene-1,3-dicarboxylate Chemical compound C=1C=CC(C(=O)OCC=2C=CC=CC=2)=CC=1C(=O)OCC1=CC=CC=C1 OIVQLSUKOZNNCT-UHFFFAOYSA-N 0.000 description 1
- KKMCIRDYHDDOEL-UHFFFAOYSA-N dicyclohexyl 4-hydroxybenzene-1,2-dicarboxylate Chemical compound C1CCCCC1OC(=O)C1=CC(O)=CC=C1C(=O)OC1CCCCC1 KKMCIRDYHDDOEL-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IAJNXBNRYMEYAZ-UHFFFAOYSA-N ethyl 2-cyano-3,3-diphenylprop-2-enoate Chemical compound C=1C=CC=CC=1C(=C(C#N)C(=O)OCC)C1=CC=CC=C1 IAJNXBNRYMEYAZ-UHFFFAOYSA-N 0.000 description 1
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- RQAQWBFHPMSXKR-UHFFFAOYSA-N n-(4-chlorophenyl)-3-(phosphonooxy)naphthalene-2-carboxamide Chemical compound OP(O)(=O)OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=C(Cl)C=C1 RQAQWBFHPMSXKR-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
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 1
- 125000004370 n-butenyl group Chemical group [H]\C([H])=C(/[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- BYODQNZIFLYIPV-UHFFFAOYSA-N n-fluoro-3-(trifluoromethyl)aniline Chemical compound FNC1=CC=CC(C(F)(F)F)=C1 BYODQNZIFLYIPV-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-methyl phenol Natural products CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- FMJSMJQBSVNSBF-UHFFFAOYSA-N octocrylene Chemical compound C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(CC)CCCC)C1=CC=CC=C1 FMJSMJQBSVNSBF-UHFFFAOYSA-N 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- RWFHJEVTRVSDNX-UHFFFAOYSA-N phenol;propanoic acid Chemical compound CCC(O)=O.OC1=CC=CC=C1 RWFHJEVTRVSDNX-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 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
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 125000005506 phthalide group Chemical group 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- JFTNAXDYYMQUHC-UHFFFAOYSA-L zinc;4-nitrobenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=C([N+]([O-])=O)C=C1.[O-]C(=O)C1=CC=C([N+]([O-])=O)C=C1 JFTNAXDYYMQUHC-UHFFFAOYSA-L 0.000 description 1
- JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
-
- 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
- B41M5/3335—Compounds containing phenolic or carboxylic acid groups or metal salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Abstract
Heat sensitive compositions comprises a colour former compound, a developer and a stabilizer of formula (1) :- <EMI ID=1.1 HE=47 WI=96 LX=562 LY=1046 TI=CF> <PC>wherein R stands for hydrogen, C1-C8alkyl, C2-C8alkenyl, C6-C10aryl, aralkyl having seven to ten carbon atoms, aroyl, wherein aryl has 6 to 10 carbon atoms, and wherein aryl, aralkyl and aroyl radicals may be substituted one, two or three times by C1-C4alkyl, C1-C4alkoxy, or halogen, R1 stands for C1-C8alkyl, C2-C8alkenyl or C3-C10cycloalkyl, R2 stands for C1-C8alkyl or C6-C10aryl, which may be substituted one, two or three times by C1-C8alkyl, C1-C8alkoxy, or halogen. Disclosed also, is a heat sensitive recording material which comprises a stabilizer of formula (1) and use of a compound of formula (1) as a stabilizer in heat sensitive compositions and heat sensitive recording materials.
Description
Heat Sensitive ComDosition ComDrisinq Benzoic Acid Derivatives The present
invention relates to a heat sensitive composition, a heat sensitive recording material and the use of the heat sensitive composition. It more particularly relates to such recording material in the form of a supporting substrate, for example, a paper sheet, synthetic paper sheet or plastic resin film, and a thermosensitive coloured image- forming layer formed on a surface of the supporting substrate and comprising a colourless or pale coloured electron donative compound (colour forming compound), an organic electron acceptor (developer) and a compound that improves image stability (stabiliser) and a binder.
Heat sensitive recording has conventionally been used as a system for recording transferred information through the mediation of heat, by utilising a colour reaction between a colour forming compound and a developer.
The properties which are most desirable in a colour forming material, in addition to the effective development of colour, are thermal response, background whiteness and image
stability, especially light fastness of the developed colour, heat and moisture fastness of the developed colour, oil fastness of the developed colour, plasticiser resistance of the developed colour and water fastness of the developed colour.
A disadvantage of heat sensitive recording materials is the stability of the image in that the reaction of the colour former with the colour developing agent is reversible and thus the resultant coloured images fade particularly towards light over a prolonged period of time. In addition, the stability of the image is lowered when it is stored under severe conditions, for example at elevated temperatures and / or humidity, or when the recording material is brought into contact with water, an oily or fatty substance or plasticisers.
Therefore a need still exists to improve the above properties and to improve the archival capabilities of such recording materials.
Accordingly, it is an object of the present invention to provide heat sensitive compositions and heat sensitive recording materials with improved properties, especially to provide an increase in image stability whilst maintaining or improving the background whiteness of the
- 2 paper before imaging and the background whiteness of the undeveloped portion after
imaging. The present invention relates to a heat sensitive composition comprising a] a colour former compound b] a developer c] a stabiliser of formula (1) R' Rat HO, OH
R2 Go R2 COOR wherein R stands for hydrogen, C,-C8alkyl, C2-C8alkenyl, C6C,0aryl, aralkyl having seven to ten carbon atoms, aroyl, wherein aryl has 6 to 10 carbon atoms, and wherein aryl, aralkyl and aroyl radicals may be substituted one, two or three times by C,-C4alkyl, C,-C4alkoxy, or halogen, R. stands for C,-CBalkyl, C2-C8alkenyl or C=C,Ocycloalkyl, R2 stands for C,-C8alkyl or C6-C,0aryl, which may be substituted one, two or three times by C,-C8alkyl, C,-C8alkoxy, or halogen.
C,-C8alkyl may be linear or branched (where possible) and stands e.g. for methyl, ethyl, n-, i-
propyl, n-, i-, sec.-, tert.-butyl, n-pentyl, isoamyl, n-hexyl, n-heptyl, n-octyl, preferably for C,-
C4alkyl such as methyl, ethyl, n-, i-propyl, n-, i-, sec.-, tert.-butyl, most preferably for methyl or ethyl; C,-C8alkoxy stands for methoxy, ethoxy, n-propoxy, n-butoxyl, n-pentoxy, n-hexoxy, n-
heptoxy, n-octoxy, preferably for C,-C4alkoxy such as methoxy, ethoxy, npropoxy, n-butoxy;
C2-CBalkenyl can be linear or branched (where possible) and stands e.g. for ethenyl (vinyl), n-propenyl, 2-propenyl (ally!), isopropenyl (1methylvinyl), n-butenyl, n-pentenyl, n-hexenyl, n-heptenyl or n-octenyl, preferably for allyl; C3-CBcycioalkyl stands for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl, preferably cyclohexyl; halogen stands for fluorine, chlorine, bromine, iodine, aralkyl of 7-10 carbon atoms stands for benzyl, 2-phenylethyl, 3phenylpropyl, 4-phenylbutyl.
A preferred embodiment of this invention relates to a heat sensitive composition, in which the stabilizer has the formula (2) or (3) (2) R2 R2
BOOR R1 R1 ICY (3)
R2, R2
COOR The stabilisers of formulae (1), (2) and (3) are exemplified by but not limited to: 4-[bis(4-hydroxy-2,5-dimethylphenyl)methyl]benzoic acid, 4-[bis(4-hydroxy-2,5-di-tert butylphenyl)methyl]benzoic acid, 4-[bis(4hydroxy-2-tert-butyl-5-ethylphenyl)methyl]benzoic acid, 4-[bis(4-hydroxy2-isopropyl-5-methylphenyl)methyl]benzoic acid, 4-[bis(4-hydroxy-2 cyclohexyl-5-methylphenyl)methyl]benzoic acid, 4-[bis(4-hydroxy-2-tertbutyl-5
- 4 methylphenyl)methyl]benzoic acid, 4-[bis(4-hydroxy-2-methyl-5-
isopropylphenyl)methyl]benzoic acid, 4-[bis(4-hydroxy-2-cyclohexyl-5-(2-
methylphenyl)phenyl)methyl]benzoic acid, 4-[bis(4-hydroxy-2- (1,1dimethylpropyl)-5-
methylphenyl)methyl]benzoic acid, 3-[bis(4-hydroxy-2,5-dimethylphenyl) methyl]benzoic acid, 3-[bis(4-hydroxy-2,5-di-tert-
butylphenyl)methyl]benzoic acid, 3-[bis(4-hydroxy-2-tert-butyl-5ethylphenyl)methyl]benzoic acid, 3-[bis(4-hydroxy-2-isopropyl-5methylphenyl)methyl]benzoic acid, 3-[bis(4-hydroxy-2-
cyclohexyl-5-methylphenyl)methyl]benzoic acid, 3-[bis(4-hydroxy-2-tertbutyl-5-
methylphenyl)methyl]benzoic acid, 3-[bis(4-hydroxy-2-methyl-5-
isopropylphenyl)methyt]benzoic acid, 3-[bis(4-hydroxy-2-cyclohexyl-5-(2-
methylphenyl)phenyl)methyl]benzoic acid, 3-[bis(4-hydroxy-2- (1,1dimethylpropyl)-5-
methylphenyl)methyl]benzoic acid, 4-[bis(4-hydroxy-2,5-dimethylphenyl) methyl]benzoic acid methyl ester, 4-[bis(4-hydroxy-2,5-
di-tert-butylphenyl)methyl]benzoic acid methyl ester, 4-[bis(4-hydroxy-2tert-butyl-5-
ethylphenyl)methyl]benzoic acid methyl ester, 4-[bis(4-hydroxy-2isopropyl-5-
methylphenyl)methyl]benzoic acid methyl ester, 4-[bis(4-hydroxy-2cyclohexyl-5-
methylphenyl)methyl]benzoic acid methyl ester, 4-[bis(4-hydroxy-2-tertbutyl-5-
methylphenyl)methyl]benzoic acid methyl ester, 4-[bis(4-hydroxy-2-methyl5-
isopropylphenyl)methyl]benzoic acid methyl ester, 4-[bis(4-hydroxy-2cyclohexyl-5-(2-
methylphenyl)phenyl)methyl]benzoic acid methyl ester, 4-[bis(4-hydroxy-2(1,1-
dimethylpropyl)-5-methylphenyl)methyl]benzoic acid methyl ester, 3-[bis(4hydroxy-2,5-dimethylphenyl)methyl]benzoic acid methyl ester, 3-[bis(4hydroxy-2,5-
di-tert-butylphenyl)methyl]benzoic acid methyl ester, 3-[bis(4-hydroxy-2tert-butyl-5-
ethylphenyl)methyl]benzoic acid methyl ester, 3-[bis(4-hydroxy-2isopropyl-5-
methylphenyl)methyl]benzoic acid methyl ester, 3-[bis(4-hydroxy-2cyclohexyl-5-
methylphenyl)methyl]benzoic acid methyl ester, 3-[bis(4-hydroxy-2-tertbutyl-5-
methylphenyl)methyl]benzoic acid methyl ester, 3-[bis(4-hydroxy-2-methyl5-
isopropylphenyl)methyl]benzoic acid methyl ester, 3-[bis(4-hydroxy-2cyclohexyl-5-(2-
methylphenyl)phenyl)methyl]benzoic acid methyl ester, 3-[bis(4-hydroxy-2(1,1-
dimethylpropyl)-5-methylphenyl)methyl]benzoic acid methyl ester,
4-[bis(4-hydroxy-2,5-dimethylphenyl)methyl]benzoic acid ethyl ester, 4[bis(4-hydroxy-2,5-di-
tert-butylphenyl)methyl]benzoic acid ethyl ester, 4-[bis(4-hydroxy-2-tertbutyl-5-
ethylphenyl)methyl]benzoic acid ethyl ester, 4-[bis(4-hydroxy-2-isopropyl5-
methylphenyl)methyl]benzoic acid ethyl ester, 4-[bis(4-hydroxy-2cyclohexyl-5-
methylphenyl)methyl]benzoic acid ethyl ester, 4-[bis(4-hydroxy-2-tertbutyl-5-
methylphenyl)methyl]benzoic acid ethyl ester, 4-[bis(4-hydroxy-2-methyl-5-
isopropylphenyl)methyl]benzoic acid ethyl ester, 4-[bis(4-hydroxy-2cyclohexyl-5-(2-
methylphenyl)phenyl)methyl]benzoic acid ethyl ester, 4-[bis(4-hydroxy-2(1,1-
dimethylpropyl)-5-methylphenyl)methyl]benzoic acid ethyl ester, 3-[bis(4hydroxy-2,5-dimethylphenyl)methyl]benzoic acid ethyl ester, 3-[bis(4hydroxy-2,5-di-
tert-butylphenyl)methyl]benzoic acid ethyl ester, 3-[bis(4-hydroxy-2-tertbutyl-5-
ethylphenyl)methyl]benzoic acid ethyl ester, 3-[bis(4-hydroxy-2-isopropyl5-
methylphenyl)methyl]benzoic acid ethyl ester, 3-[bis(4-hydroxy-2cyclohexyl-5-
methylphenyl)methyl]benzoic acid ethyl ester, 3-[bis(4-hydroxy-2-tertbutyl-5-
methylphenyl)methyl]benzoic acid ethyl ester, 3-[bis(4-hydroxy-2-methyl-5-
isopropylphenyl)methyl]benzoic acid ethyl ester, 3-[bis(4-hydroxy-2cyclohexyl-5-(2-
methylphenyl)phenyl)methyl]benzoic acid ethyl ester, 3-[bis(4-hydroxy-2(1,1-
dimethylpropyl)-5-methylphenyl)methyl]benzoic acid ethyl ester.
All the exemplified stabilisers can be used singly or as a mixture with other stabilizers.
The weight ratio of the stabiliser, as represented by formulae (1), (2) and (3) to colour former can be in the range 0.05:1.0 to 1.0:1.0, preferably from 0.1:1.0 to 0.7:1.0, most preferably 0.5 (+0.05):1.0 (+0. 05).
The stabilisers of formulae (1), (2) and (3) can be prepared by the reaction of a phenol of formula (4) R1 OH (4) R2 with an aldehyde of formulae (5), (6), or (7)
- 6 CHO CHO CHO
POOH OH COOH
(5) (6) (7)
in the presence of a solvent such as water and a catalyst such as hydrochloric acid as described e.g. in Japanese patent JP2676902 B2.
The carboxylic acid esters of formulae (1), (2) and (3) where R is as defined, may be prepared by esterification of the corresponding, preferably isolated, carboxylic acid derivatives or - if R is chooser to be alkyl - by carrying out the condensation reaction of the substituted phenol and the carboxybenzaldehyde (5) to (7) with an aliphatic alcohol ROH as solvent. In a preferred embodiment, R stands for C'-C4alkyl, and most preferably ROH stands for methanol or ethanol.
The colour forming compounds are, for example, triphenylmethanes, lactones, benzoxazines, spiropyrans, fluorans, phthalides and azaphthalides, preferably fluorans.
Preferred colour farmers include, but are not limited to 3-diethylamino-6methylfluoran, 3-
dimethylamino-6-methyl-7-anilinofluoran (including the crystal modification disclosed in EP-A 928,794), 3-diethylamino-6-methyl-7anilinofluoran, 3-diethylamino-6-methyl-7-(2,4-
dimethylanilino) fluoran, 3-diethylamino-6-methyl-7-chlorofluoran, 3diethylamino-6-methyl-7-
(3-trifluoromethylanilino) fluoran, 3-diethylamino-6-methyl-7-(2chloroanilino) fluoran, 3-
diethylamino-6-methyl-7-(4-chloroanilino) fluoran, 3-diethylamino-6methyl-7-(2-fluoroanilino) fluoran, 3-diethylamino-6-methyl-7-(4-noctylanilino) fluoran, 3-diethylamino -7-(4-n-
octylanilino) fluoran, 3-diethylamino -7-(n-octylamino) fluoran, 3diethylamino -7-
(dibenzylamino) fluoran, 3-diethylamino-6-methyl-7-(dibenzylamino) fluoran, 3-diethylamino-
6-chloro-7-methylfluoran, 3-diethylamino-7-t-butylfluoran, 3-diethylamino -7-
carboxyethylfluoran, 3-diethylamino-6-chloro-7-anilinofluoran, 3diethylamino-6-methyl-7-(3-
methylanilino) fluoran, 3-diethylamino-6-methyl-7-(4-methylanilino) fluoran, 3-diethylamino-6-
ethoxyethyl-7-anilinofluoran, 3-diethylamino-7-methylfluoran, 3diethylamino-7-chlorofluoran, 3-diethylamino-7-(3-trifluoromethylanilino) fluoran, 3-diethylamino-7-(2-chloroanilino) fluoran, 3-diethylamino-7-(2fluoroanilino) fluoran, 3-diethylamino-benzo[a] fluoran, 3-diethylamino-
benzo[c] fluoran, 3-dibutylamino-7-dibenzylaminofluoran, 3-dibutylamino-7anilinofluoran, 3
- 7 diethylamino-7-anilinofluoran, 3-dibutylamino-6-methyl fluoran, 3dibutylamino-6-methyl-7-
anilinofluoran, 3-dibutylamino-6-methyl-7-(2,4-dimethylanilino) fluoran, 3-dibutylamino-6-
methyl-7-(2-chloroanilino) fluoran, 3-dibutylamino-6-methyl-7-(4chloroanilino) fluoran, 3-
dibutylamino-6-methyl-7-(2-fluoroaniiino) fluoran, 3-dibutylamino-6methyl-7-(3-
trifluoromethylanilino) fluoran, 3-dibutylamino-6-ethoxyethyl-7anilinofluoran, 3-dibutylamino-
6-chloro-anilinofluoran, 3-dibutylamino-6-methyl-7-(4-methylanilino) fluoran, 3-dibutylamino-
7-(2-chloroaniiino) fluoran, 3-dibutylamino-7-(2-fluoroanilino) fluoran, 3-dipentylamino-6-
methyi-7-anilinofluoran, 3-dipentylamino-6-methyl-7-(2-chloroanilino) fluoran, 3-
dipentylamino-6-methyl-7-(4-chloroanilino) fluoran 3-dipentylamino-7-(3-
trifluoromethylanilino) fluoran, 3-dipentylamino-6-chloro-7anilinofluoran, 3-dipentylamino-7-
(4-chloroanilino) fluoran, 3-pyrrolidino-6-methyl-7-anilinofluoran, 3piperidino-6-methyl-7-
anilinofluoran, 3-(N-methyl-N-propylamino)-6-methyl-7-anilinofluoran, 3(N-methyl-N-
cyclohexylamino)-6-methyl-7-anilinofluoran, 3-(N-ethyl-N-cyclohexylamino)6-methyl-7-
anilinofluoran, 3-(N-ethyl-p-toluidino)-6-methyl-7-anilinofluoran, 3-(Nethyl-N-isoamylamino)-
6-methyl-7-anilinofluoran, 3-(N-ethyl-N-isoamylamino)-6-chloro-7anilinofluoran, 3-(N-ethyl-N-
tetrahydrofurfurylamino)-6-methyl-7-anilinofluoran, 3-(N-ethyl-Nisobutylamino)-6-methyi-7-
anilinofluoran, 3-(N-butyl-N-isoamylamino)-6-methyl-7-anilinofluoran, 3(N-isopropyl-N-3-
pentylamino)-6-methyl-7-anilinofluoran, 3-(N-ethyl-N-ethoxypropylamino)-6methyl-7-
anilinofluoran, 3-cyclohexylamino-6-chlorofluoran, 2-methyl-6-p-(p-
dimethylaminophenyl)aminoanilinofluoran, 2-methoxy-6-p-(p-
dimethylaminophenyl)aminoanilinofluoran, 2-chloro-3-methyl-6-p-(p-
phenylaminophenyl)aminoanilinofluoran, 2-diethylamino-6-p-(p-
dimethylaminophenyl)aminoanilinofluoran, 2-phenyl-6-methyl--6-p-(p-
phenylaminophenyl)aminoanilinofluoran, 2-benzyl-6-p-(p-
phenylaminophenyl)aminoanilinofluoran, 3-methyl-6-p-(p-
dimethylaminophenyl)aminoanilinofluoran, 3-diethylamino-6-p-(p-
diethylaminophenyl)aminoanilinofluoran, 3-diethylamino-6-p-(p-
dibutylaminophenyl)aminoanilinofluoran, 2,4-dimethyl-6-[(4-dimethylamino) anilino] fluoran, 3-
[(4-dimethylaminophenyl)amino]-5,7-dimethylfluoran, 3,6,6'-
tris(dimethylamino)spiro[fluorene-9,3'-phthalide], 3,6,6'tris(diethylamino)spiro[fluorene-9,3'-
phthalide], 3,3-bis(p-dimethylaminophenyl)-6-dimethylaminophthalide, 3,3bis(p-
dimethylaminophenyl)phthalide, 3,3-bis-[2-(p-dimethylaminophenyl)-2-(p-
methoxyphenyl)ethenyl-4,5,6,7-tetrabromophthalide,
- 8 3,3-bis-2-(p-dimethylaminophenyl)-2-(p-methoxyphenyl)ethenyl-4,5,6,7tetrachlorophthalide, 3,3-bis[1,1-bis(4-pyrrolidinophenyl)ethylene-2-yl]4,5,6,7-tetrabromophthalide, 3,3-bis-[1-(4-
methoxyphenyl)-1-(4-pyrridinophenyl)ethylene-2-yl]-4,5,6,7tetrachlorophthaiide, 3-(4-
diethylamino-2-ethoxyphenyl)-3-(1-ethyl-2-methylindole-3-yl)-4azaphthalide, 3-(4-
diethylamino-2-ethoxyphenyl)-3-(1-octyl-2-methylindole-3-yl)-4azaphthalide, 3-(4-
cyclohexylethylamino-2-methoxyphenyl)-3-(1-ethyl-2-methylindole-3-yl)-4azaphthalide, 3,3-
bis(1-ethyl-2-methylindole-3-yl) phthalide, 3,3-bis(1-octyl-2methylindole-3-yl) phthalide, mixture of 2-phenyl-4-(4-diethylaminophenyl) -4-(4-methoxyphenyi)-6-methyl-7-
dimethylamino-3,1-benzoxazine and 2-phenyl-4-(4-diethylaminophenyl)-4-(4-
methoxyphenyl)-8-methyl-7-dimethylamino-3,1-benzoxazine, 4,4'-[1-
methylethylidene)bis(4, 1 -phenyleneoxy-4,2-quinazolinediyl)]bis[N, Ndiethylbenzenamine], bis(N-methyidiphenylamine)-4-yl-(N-butylcarbazole)-3yl-methane and mixtures thereof.
All of the above colour forming compounds can be used singly or as a mixture with other colour forming compounds; or they may also be used together with further black colour forming compounds.
Highly preferred are 3-diethylamino-6-methyl-7-anilinofluoran, 3diethylamino-6-methyl-7-(3-
methylanilino) fluoran, 3-diethylamino-6-methyl-7-(2,4-dimethylanilino) fluoran, 3-
dibutylamino-6-methyl-7-anilinofluoran, 3-dipentylamino-6-methyl-7anilinofluoran, 3-(N-
methyl-N-propylamino)-6-methyl-7-anilinofluoran, 3-(N-methyl-Ncyclohexylamino)-6-methyl-
7-anilinofluoran, 3-(N-ethyl-N-isoamylamino)-6-methyl-7-anilinofluoran, 3diethylamino-6-
chloro-7-anilinofluoran, 3-dibutylamino-7-(2-chloroanilino)fluoran, 3-(Nethyl-N-p-toluidino)-6-
methyl-7-anilinofluoran, 3-(N-ethyl-N-tetrahydrofurfurylamino)-6-methyl-7anilinofluoran, 3-(N-
ethyl-N-isobutylamino)-6-methyl-7-anilinofluoran, 3-N-ethyi-Nethoxypropylamino-6-methyl-7-
anilinofluoran, 2,4-dimethyl-6-[(4-dimethylamino)anilino]fluoran and mixtures thereof.
It is also possible to use solid solutions comprising at least two colour forming compounds as described in WO 00/12318.
The monophase solid solutions can be used singly or as a mixture with other colour forming compounds such as triphenylmethanes, lactones, fluorans, benzoxazines and spiropyrans; or they may also be used together with further black colour forming compounds. Examples of such other colour forming compounds are given hereinbefore.
- 9 - In addition, the heat sensitive composition contains a developer. Such developers are exemplified by, but not limited to 4,4'isopropylidene bisphenol, 4,4'-sec-butylidene bisphenol, 4,4'cyclohexyiidene bisphenol, 2,2-bis-(4-hydroxyphenyl)-4-methylpentane, 2,2-
dimethyl-3,3-di(4-hydroxyphenyl)butane, 2,2'-dihydroxydiphenyl, 1-phenyl1,1-bis(4-
hydroxyphenyl)butane, 4-phenyl-2,2-bis(4-hydroxyphenyl)butane, 1-phenyl-2, 2-bis(4-
hydroxyphenyl)butane, 2,2-bis(4'-hydroxy-3'-methylphenyl)-4-methylpentane, 2,2-bis(4'-
hydroxy-3'-tert-butylphenyl)-4-methylpentane, 4,4'-sec-butylidene-bis (2methylphenol), 4,4'-
isopropylidene-bis (2-tert-butylphenol), 2,2-bis(4'-hydroxy-3'isopropylphenyi)-4-
methylpentane, allyl-4,4-bis (4'-hydroxyphenyl) pentanoate, propargyl-4,4bis(4'-
hydroxyphenyl) pentanoate, n-propyl-4,4-bis (4'-hydroxyphenyl) pentanoate, 2,4-bis (phenylsulfonyl) phenol, 2-(4-methylsulfonyl)-4-(phenylsulfonyl) phenol, 2-(phenylsulfonyl)-4-
(4-methylsulfonyl) phenol, 2,4-bis (4-methylphenylsulfonyl) phenol, pentamethylene-bis(4-
hydroxybenzoate), 2,2-dimethyl-3,3-di(4-hydroxyphenyl)pentane, 2,2-di(4-
hydroxyphenyl)hexane, 4,4'-dihydroxydiphenyl thioether, 1,7-di(4hydroxyphenylthio)-3,5-
dioxaheptane, 2,2'-bis(4-hydroxyphenylthio)diethyl ether, 4,4'-dihydroxy3,3'-dimethylphenyl thioether; benzyl-4-hydroxybenzoate, ethyl-4hydroxybenzoate, propyl-4-hydroxybenzoate, isopropyl-4-hydroxybenzoate, butyl-4-hydroxybenzoate, isobutyl-4-hydroxybenzoate, 4,4'-
dihydroxydiphenyl sulfone, 2,4'-dihydroxydiphenyl sulfone, 4-hydroxy-4'methyidiphenyl sulfone, 4-hydroxy-4'-isopropoxydiphenyl sulfone, 4hydroxy-4'-butoxydiphenyl sulfone, 4,4'-
dihydroxy-3,3'-diallyidiphenyl sulfone, 3,4-dihydroxy-4'-methyidiphenyl sulfone, 4,4'-
dihydroxy-3,3',5,5'-tetrabromodiphenyl sulfone, 4,4'-bis (p-
toluenesulphonylaminocarbonylamino) diphenylmethane, N-p-toluenesulphonylN'-phenyl urea, N-p-toluenesulphonyl-N'-[3-0-p-toluenesulphonyl]phenyl urea, dimethyl 4-
hydroxyphthalate, dicyclohexyl 4-hydroxyphthalate, diphenyl 4hydroxyphthalate, 4-[2-(4-
methoxyphenyloxy)ethyloxy] salicylate, 3,5-di-tert-butylsalicylic acid, 3benzyl salicylic acid, 3-(a-methylbenzyl) salicylic acid, 3-phenyl-5-(a,adimethylbenzyl) salicylic acid, 3,5-di-a-
methylbenzyl salicylic acid; metal salts of salicylic acid, 2benzylsulfonylbenzoic acid, 3-
cyclohexyl-4-hydroxybenzoic acid, zinc benzoate, zinc 4-nitrobenzoate, 4(4'-
phenoxybutoxy)phthalic acid, 4-(2'-phenoxyethoxy)phthalic acid, 4-(3'-
phenylpropyloxy)phthalic acid, mono (2-hydroxyethyl) -5-nitro-isophthalic acid, 5-
benzyloxycarbonyl isophthalic acid, 5-(1'-phenylethanesulfonyl) isophthalic acid, bis(1,2-
dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one-O)bis(thiocyanato-N) zinc and mixtures thereof.
- lo -
The weight ratio of developer to colour former usually is chosen in the range of from 1:1 to 5:1, preferably from 2:1 to 3:1.
Another object of the present invention relates to a heat sensitive recording material, which comprises the inventive heat sensitive composition and a substrate.
In a preferred embodiment, the heat sensitive recording material comprises a sheet substrate and a thermosensitive coloured image forming layer formed on the surface of the supporting substrate, comprising the inventive heat sensitive composition, a colourless or pale coloured colour forming compound, a colour developing agent reactive with the colour former upon heating to thereby develop a colour, and a binder.
Usually the binder is added in an effective amount. As a rule the weight ratio of binder to colour former is chosen in the range of from 1:1 to 3:1.
Another preferred embodiment of the invention relates to the inventive heat sensitive recording material, wherein the recording material comprises a colour forming compound that will generate a blue image. Preferably the colour forming compound is selected from the group consisting of 3,3-bis(p-dimethylaminophenyl)-6-dimethylaminophthalide,3(4-
diethylamino-2-ethoxyphenyl)-3-(1-ethyl-2-methylindole-3-yl)-4azaphthalide, and 3-(4-
diethylamino-2-ethoxyphenyl)-3-( 1 -octyl-2-methylindole-3-yl)-4azaphthalide.
Another preferred embodiment of the invention relates to the inventive heat sensitive recording material, wherein the recording material comprises a colour forming compound that will generate a green image. Preferably the color forming compound is 3-diethylamino-7-
(dibenzylamino) fluoran.
Another preferred embodiment of the invention relates to the inventive heat sensitive recording material, wherein the recording material comprises a colour forming compound that will generate an orange image. Preferably the colour forming compound is selected from the group consisting of 3-diethylamino-7-t-butylfluoran and 3-diethylamino-7carboxyethylfluoran.
Another preferred embodiment of the invention relates to the inventive heat sensitive recording material, wherein the recording material comprises a colour forming compound that
will generate a red image. Preferably the colour forming compound is selected from the group consisting of 3,3-bis(1-ethyl-2methylindole-3-yl) phthalide, 3,3-bis(1-octyi-2-
methylindole-3-yl)phthalide, 9-(diethyiamino)-spiro[1 2H-benzo[a]xanthene12, 1 '(3'H)-
isobenzofuran]-3'-one, and 6-(N-ethyl-N-4-methylphenyl)amino-2methylfluoran.
In addition, the heat sensitive composition as well as the heat sensitive recording material of the invention can contain a sensitizer.
Representative examples of sensitiser are stearamide, methylol stearamide, p-
benzylbiphenyl, m-terphenyl, 2-benzyloxynaphthalene, 4-methoxybiphenyl, dibenzyl oxaiate, di(4-methylbenzyl) oxalate, di(4-chlorobenzyl) oxalate, dimethyl phthalate, dibenzyl terephthalate, dibenzyl isophthalate, 1,2diphenoxyethane, 1,2-bis(4-methylphenoxy) ethane, 1,2-bis(3-methylphenoxy) ethane, 4,4'-dimethylbiphenyl, phenyl-1-hydroxy-2-naphthoate, 4-
methylphenyl biphenyl ether, 1,2-bis(3,4-dimethylphenyl) ethane, 1,4diethoxynaphthalene, 1,4-diacetoxybenzene, 1,4-diproprionoxybenzene, oxylylene-bis(phenyl ether), 4-(m-
methylphenoxymethyl) biphenyl, p-hydroxyacetanilide, phydroxybutyranilide, p-
hydroxynonananilide, p-hydroxylauranilide, p-hydroxyoctadecananilide.
The above sensitisers are known or can be prepared according to known methods.
Usually the sensitizer is added in an effective amount. As a rule the weight ratio of sensitizer to color former is chosen in the range of from 1:1 to 3:1.
The heat sensitive composition and the heat sensitive recording material of the invention can be prepared according to conventional methods. For example, a colour former compound, a developer, optionally a sensitiser are pulverised separately in water or a suitable dispersing medium, such as aqueous polyvinyl alcohol, to form an aqueous or other dispersion. A compound of formula (1), (2) or (3) is treated in the same manner. The fine particle dispersions thus obtained are combined and - if the heat sensitive recording material is manufactured - then mixed with conventional amounts of binder, filler and lubricant.
Representative binders used for the heat sensitive recording material include polyvinyl alcohol (fully and partially hydrolysed), carboxy, amide, sulfonic and butyral modified polyvinyl alcohols, derivatives of cellulose such as hydroxyethyl cellulose, methyl cellulose, ethyl cellulose, carboxymethyl cellulose and acetyl cellulose, copolymer of styrene-maleic
- 12 anhydride, copolymer of styrene-butadiene, polyvinyl chloride, polyvinyl acetate, polyacrylamide, polyamide resin and mixtures thereof.
Exemplary fillers, which can be used include calcium carbonate, kaolin, calcined kaolin, aluminium hydroxide, talc, titanium dioxide, zinc oxide, silica, polystyrene resin, urea-
formaldehyde resin, hollow plastic pigment and mixtures thereof.
Representative lubricants for use in heat sensitive recording materials include stearamide, methylene bisstearamide, polyethylene, carnauba wax, paraffin wax, zinc stearate or calcium stearate and mixtures thereof.
Other additives can also be employed, if necessary. Such additives are for example fluorescent whitening agents and ultraviolet absorbers. The ultraviolet absorbers may be employed in either the thermosensitive colouring layer or in a protective layer, and if desired, may be used in microencapsulated form in the protective layer.
Representative examples of ultraviolet absorbers that may be used in the invention include phenyl salicylate, p-tert-butylphenyl salicylate, poctylphenyl salicylate and like salicylic acid type ultraviolet absorbers, 2,4-Dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-
octyloxybenzophenone, 2-hydroxy-4-dodecyloxybenzophenone, 2,2'-dihydroxy4-
methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2-hydroxy4-methoxy-
5-sulfobenzophenone and like benzophenone type ultraviolet absorbers; 2Ethylhexyl-2-cyano-3,3-diphenylacrylate, ethyl-2-cyano-3,3diphenylacrylate and like cyanoacrylate type ultraviolet absorbers, Bis(2, 2,6,6-tetramethyl-4-piperidyl) sebacate, bis(2,2,6,6-tetramethyl-4piperidyl) succinate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)-2-(3,5-ditert-butyl-4-hydroxybenzyl)-2-n-butyl malonate and like hindered amine type ultraviolet absorbers, 2-(2'-Hydroxyphenyl) benzotriazole, 2-(2'hydroxy-5'-methylphenyl) benzotriazole, 2-(2'-
hydroxy-5'-tert-butylphenyl)benzotriazole, 2-(2'-hydroxy-3,5'-di-tertbutylphenyl) benzotriazole, 2-(2'-hydroxy-3'-tert-butyl-5'-methylphenyl)5-chlorobenzotriazole, 2-(2'-
hydroxy-3,5'-di-tert-butylphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-3, 5'-di-tert
- 1 3 butylphenyl)-5-tert-butylbenzotriazole, 2-(2'-hydroxy-3,5'-di-tertamylphenyl) benzotriazole, 2-
(2'-hydroxy-3,5'-di-tert-amylphenyl)-5-tert-amyibenzotriazole, 2-(2'hydroxy-3,5'-di-tert-
amylphenyl)-5-methoxybenzotriazole, 2-[2'-hydroxy-3'-(3",4",5",6"tetrahydrophthalimido-
methyl)-5'-methylphenyl] benzotriazole, 2-(2'-hydroxy-5'-tert-octylphenyl) benzotriazole, 2-(2'-
hydroxy-3'-sec-butyl-5'-tert-butylphenyl) benzotriazole, 2-(2'-hydroxy-3'tert-amyi-5'-
phenoxyphenyl)-5-methylbenzotriazole, 2-(2'-hydroxy-5'-n-dodecylphenyl) benzotriazole, 2-
(2'-hydroxy-5'-sec-octyloxyphenyl)-5-phenylbenzotriazole, 2-(2'-hydroxy3'-tert-amyl-5'-
phenylphenyl)-5-methoxybenzotriazole, 2-[2'-hydroxy-3',5'-bis(a,adimethylbenzyl)-phenyl] benzotriazole and like benzotriazole ultraviolet absorbers, 2-(2'-Hydroxy-3'-dodecyl-5'-methylphenyl) benzotriazole, 2-(2'hydroxy-3'-undecyl-5'-
methylphenyl) benzotriazole, 2-(2'-hydroxy-3'-tridecyl-5'-methylphenyl) benzotriazole, 2-(2'-
hydroxy-3'-tetradecyl-5'-methylphenyl) benzotriazole, 2-(2'-hydroxy-3'pentadecyl-5'-
methylphenyl) benzotriazole, 2-(2'-hydroxy-3'-hexaadecyl-5'-methylphenyl) benzotriazole, 2-
[2'-hydroxy-4'-(2"-ethylhexyl)oxyphenyl] benzotriazole, 2-[2'-hydroxy-4'(2"-
ethylheptyl)oxyphenyl] benzotriazole, 2-[2'-hydroxy-4'-(2"-ethyloctyl) oxyphenyl] benzotriazole, 2-[2'-hydroxy-4'-(2"-propyloctyl)oxyphenyl] benzotriazole, 2-[2'-hydroxy-4'-(2"-
propylheptyl)oxyphenyl] benzotriazole, 2-[2'-hydroxy-4'-(2"-propylhexyl)oxyphenyl] benzotriazole, 2-[2'-hydroxy-4'-(1"-ethylhexyl)oxyphenyl] benzotriazole, 2-[2'-hydroxy-4'-(1"-
ethylheptyl)oxyphenyl] benzotriazole, 2-[2'-hydroxy-4'-(1"-ethyloctyl) oxyphenyl] benzotriazole, 2-[2'-hydroxy-4'-(1"-propyloctyl)oxyphenyl] benzotriazole, 2-[2'-hydroxy-4'-(1"-
propylheptyl)oxyphenyl] benzotriazole,, 2-[2'-hydroxy-4'-(1"-propylhexyl) oxyphenyl] benzotriazole, 2-(2'-hydroxy-3'-sec-butyl-5'-tert-butylphenyl)5-n-butylbenzotriazole, 2-(2'-
hydroxy-3'-sec-butyl-5'-tert-butylphenyl)-5'-tert-pentylbenzotriazole, 2(2'-hydroxy-3'-sec-
butyl-5'-tert-butylphenyl)-5-n-pentylbenzotriazole, 2-(2'-hydroxy-3'-secbutyl-5'-tert-
pentylphenyl)-5'-tert-butylbenzotriazole, 2-(2'-hydroxy-3'-sec-butyl-5'tert-pentylphenyl)-5'-n-
butylbenzotriazole, 2-(2'-hydroxy-3',5'-di-tert-butylphenyl)-5-secbutylbenzotriazole, 2-(2'-
hydroxy-3',5'-di-tert-pentylphenyl)-5-sec-butylbenzotriazole, 2-(2'hydroxy-3'-tert-butyl-5'-tert-
pentylphenyl)-5-sec-butylbenzotriazole, 2-(2'-hydroxy-3,5'-di-secbutylphenyl)-5-
chlorobenzotriazole, 2-(2'-hydroxy-3,5'-di-sec-butylphenyl)-5methoxybenzotriazole, 2-(2'-
hydroxy-3,5'-di-sec-butylphenyl)-5-tert-butylbenzotriazole, 2-(2'-hydroxy3,5'-di-sec-
butylphenyl)-5-n-butylbenzotriazole, octyl-5-tert-butyl-3-(5-chloro-2Hbenzotriazole-2-yl)-4-
hydroxybenzene propionate, condensate of methyl -3-[tert-butyl-5-(2Hbenzotriazole-2-yl)-4
- 14 hydroxyphenyl] propionate and polyethylene glycol (molecular weight: about 300) and like benzotriazole ultraviolet absorbers.
The coating liquid so obtained can be applied to a suitable substrate such as paper, plastic sheet and resin coated paper, and used as the heat sensitive recording material. The system of the invention can be employed for other end use applications using colour forming materials, for example, a temperature indicating material.
The quantity of the coating is usually in the range of 2 to 10 g/m2, most often in the range 4 to 8 gim2.
The recording material containing such a thermosensitive colouring layer can in addition contain a protective layer and, if desired, an undercoat layer. The undercoat layer may be interposed between the substrate and the thermosensitive colouring layer.
The protective layer usually comprises a water-soluble resin in order to protect the thermosensitive colouring layer. If desired, the protective layer may contain water-soluble resins in combination with waterinsoluble resins.
As such resins conventional resins can be employed. Specific examples are: polyvinyl alcohol; starch and starch derivatives; cellulose derivatives such as methoxycellulose, hydroxyethylcellulose, carboxymethylcellulose, methylcellulose and ethylcellulose; sodium polyacrylate; polyvinyl pyrrolidone; polyacrylamide/acrylic acid ester copolymers; acrylamide/acrylic acid ester/methacrylic acid copolymers; alkali metal salts of styrene/maleic anhydride copolymers; alkali metal salts of isobutylene/maleic anhydride copolymers; polyacrylamide; sodium alginate; gelatin; casein; water-soluble polyesters and carboxyl-group- modified polyvinyl alcohols.
The protective layer may also contain a water-resisting agent such as a polyamide resin, polyamido-epichlorhydrin resin, melamine-formaldehyde resin, formaldehyde, glyoxal or chromium alum.
Furthermore, the protective layer may contain fillers, such as finelydivided inorganic powders, e.g. of calcium carbonate, silica, zinc oxide, titanium oxide, aluminium hydroxide,
- 15 zinc hydroxide, barium sulphate, clay, talc, surface-treated calcium or silica, or a finely-
divided organic powder of, e.g., a urea-formaldehyde resin, a styrene/methacrylic acid copolymer or polystyrene.
The undercoat layer usually contains as its main components a binder resin and a filler.
Specific examples of binder resins for use in the undercoat layer are: polyvinyl alcohol; starch and starch derivatives; cellulose derivatives such as methoxycellulose, hydroxyethyicellulose, carboxymethylcellulose, methylcellulose and ethylcellulose; sodium polyacrylate; polyvinyl pyrrolidone; polyacrylamide/acrylic acid ester copolymers; acrylamide/acrylic acid ester/methacrylic acid copolymers; alkali metal salts of styrene/maleic anhydride copolymers; alkali metal salts of isobutylene/maleic anhydride copolymers; polyacrylamide; sodium alginate; gelatin; casein; water-soluble polymers such as water-soluble polyesters and carboxyl-group-modified polyvinyl alcohols; polyvinyl acetate; polyurethanes; styrene/butadiene copolymers; polyacrylic acid; polyacrylic acid esters; vinyl chloride/vinyl acetate copolymers; polybutylmethacrylate; ethylene/vinylacetate copolymers and styrene/butadiene acrylic derivative copolymers.
Specific examples of fillers for use in the undercoat layer are: finelydivided inorganic powders, e.g. of calcium carbonate, silica, zinc oxide, titanium oxide, aluminium hydroxide, zinc hydroxide, barium sulphate, clay, talc, surface-treated calcium, silica or calcined clay (e.g. Ansilex, Engelhard Corp.), and finely-divided organic powders of, e.g., urea-formaldehyde resins, styrene/methacrylic acid copolymers and polystyrene.
In addition, the undercoat layer may contain a water-resisting agent. Examples of such agents are given above.
In particular the invention provides exceptional resistance to plasticiser, oil and heat ageing whilst showing an improved background whiteness.
Examples
Examole 1: 4-[Bis(4-hydroxy-2,5-dimethylphenylmethyl]benzoic acid (8.0 9), ethanol (250 ml) and sulphuric acid 98% (4.0 9) are heated at reflux for 17 hours, cooled to 40 C and sodium bicarbonate (10.0 9) added. The reaction mass is filtered and the solvent removed from the filtrate. The resultant solid is washed with cold water to give 4-[bis(4-hydroxy-2,5
- 16 dimethylphenyl-methyl]benzoic acid ethyl ester in 86.0% theory yield and with a melting point of 212.9 - 213.8 C.
Example 2: Example 1 is repeated but with the ethanol being replaced by methanol as solvent. Yield of 4-[bis(4-hydroxy-2,5-dimethylphenyl-methyl] benzoic acid methyl ester: 90.6% theory, melting point 233.5 - 235.5 C.
ExamoIe 3: 4-carboxybenzaldehyde (6.0 9), 2-tert-butyl-5-methylphenol (16. 4 9), methanol (30.0 9) and hydrochloric acid 36% (13.0 9) are heated to reflux for 37 hours, cooled to room temperature and the reaction mass filtered. The filter cake is recrystallized from methanol/water to give white 4-[bis(4-hydroxy-2-tert-butyl-5-methylphenylmethyl]benzoic acid methyl ester, 80.0% theory yield and melting point 211.5 - 212.6 C.
Example 4: Dispersions A to D are prepared by grinding the compositions shown below in an attritor until an average particle size of 1-1.5,um is attained.
* DisDersion A (Colour Former) 3-dibutylamino-6-methyl-7-anilinofluoran 3. 01 parts Polyvinyl alcohol (10% aqueous solution) 10.50 parts Water 6.49 parts Dispersion B (Colour Developer) Colour developer 7.50 parts Polyvinyl alcohol (10% aqueous solution) 7.50 parts Water 22.50 parts Dispersion C (Sensitiser) Sensitiser 10.00 parts Polyvinyl alcohol (10% aqueous solution) 10.00 parts Water 20.00 parts Dispersion D (Stabiliser) Stabiliser 7.50 parts
- 1 7 Polyvinyl alcohol (10% aqueous solution) 7.50 parts Water 22.50 parts A thermal coating mixture is then prepared by combining together the following components: parts by weight Dispersion A 6.6 Dispersion B 12.5 Dispersion C 6.0 Dispersion D 2.5 Calcium Carbonate (25% aqueous dispersion) 13.2 Zinc stearate (33% aqueous dispersion) 1.5 Polyvinyl alcohol (10% aqueous solution) 6.5 fluorescent whitening agent (Ciba) TINOPALABP-X) 0.12 Water 2.58 This coating mixture is applied on one side of a base paper weighing 50 g/m2 in a coating weight of about 5.0 g/m2 and then dried. The resulting sheet is calendered by means of a laboratory calender to produce a recording sheet with excellent background whiteness.
Example 5: A coating mixture is prepared using 4-[bis(4-hydroxy-2,5-
dimethyphenyl)methyl]benzoic acid as stabiliser (Dispersion D) with Bisphenol A as developer (Dispersion B) and p-benzylbiphenyl as sensitiser (Dispersion C).
The heat sensitive recording paper obtained demonstrates good background whiteness of
the paper after application of the coating liquid and also after carrying out storage stability, i.e. resistance to light, heat and moisture, of the uncoloured portion of the coated paper.
Image stability is excellent and the performance against thermal paper coated without a stabiliser is summarised in Table 1. Additionally the recording paper obtained shows a high dynamic sensitivity.
Example 6: A coating mixture is prepared using 4-[bis(4-hydroxy-2,5-
dimethyphenyl)methyl]benzoic acid ethyl ester as stabiliser (Dispersion D) with 2,4'-
dihydroxydiphenylsulphone as developer (Dispersion B) and pbenzylbiphenyl as sensitiser (Dispersion C).
- 18 ExamoIe 7: A coating mixture is prepared using a mixture of 4-[bis(4hydroxy-2,5-
dimethyphenyl)methyl]benzoic acid (50%) and 4-[bis(4-hydroxy-2,5-
dimethyphenyl)methyl]benzoic acid ethyl ester (50%) as stabiliser (Dispersion D) with 2,4'-
dihydroxydiphenylsulphone as developer (Dispersion B) and pbenzylbiphenyl as sensitiser (Dispersion C).
Example 8: A coating mixture is prepared using 4-[bis(4-hydroxy-2,5-
dimethyphenyl)methyl]benzoic acid as stabiliser (Dispersion D) with 2,4'-
dihydroxydiphenylsulphone as developer (Dispersion B) and di(pmethylbenzyl)oxalate as sensitiser (Dispersion C).
Example 9: A coating mixture is prepared using 4-[bis(4-hydroxy-2,5-
dimethyphenyl)methyl]benzoic acid methyl ester as stabiliser (Dispersion D) with 2,4'-dihydroxydiphenylsulphone as developer (Dispersion B) and di(p-
methylbenzyl)oxalate as sensitiser (Dispersion C).
Example 10: A coating mixture is prepared using 4-[bis(4-hydroxy-2-tertbutyi-5-
methyphenyl)methyl]benzoic acid as stabiliser (Dispersion D) with 2,4'-
dihydroxydiphenylsulphone as developer (Dispersion B) and di(pmethylbenzyl)oxalate as sensitiser (Dispersion C).
Table 1
Example Initial Light- Heat and Plasticiser Cottonseed Water Image fastness Moisture resistance Oil Fastness Density Resistance resistance 5 O O + O O O
6 O O ++ + O +
7 O O + ++ O O
8 O O + O ++ O
9 O O O ++ O
10 O O ++ O O
Key: O Similar performance when compared to; against thermal paper coated without a stabiliser.
- 19 -
+ Improved performance when compared to against thermal paper coated without a stabiliser.
++ Superior performance when compared to against thermal paper coated without a stabiliser.
The different test methods are described as follows: Liahtfastness Tests (120 Hours Exposure): This test assesses the stability of the imaged and un-imaged thermal paper to sunlight.
An image is produced using an Atlantek thermal response tester model 200. The image including background is placed at a distance of 8cm below 40W fluorescent tubes emitting
artificial sunlight (approximately 1200 Lux) for 120 hours. The optical density of the image and background whiteness of the paper are measured before and after exposure with a
Macbeth 1200 series Densitometer.
Cottonseed Oil Resistance of Imane: This test assesses the stability of the image when exposed to cottonseed oil.
An image is produced using an Atlantek thermal response tester model 200. Cottonseed oil is then gravure printed onto the image, which is then stored at 40 C for 24 hours. The optical density of the image is measured using a Macbeth 1200 series Densitometer before and after exposure.
Plasticiser Resistance of Imane and Backaround:
This test assesses the stability of the image and background when exposed to PVC
containing 20-25% phthalate ester-type plasticiser.
An image is produced using an Atlantek thermal response tester model 200. The image is put into contact with the PVC under 107 g/cm2 pressure for 24 hours at 50 C. The optical density of the image and background are measured using a Macbeth 1200 series
Densitometer before and after exposure.
- 20 Waterfastness of Image: This test assesses the stability of the image after immersion in water.
An image is produced using an Atlantek thermal response tester model 200. The image is immersed in de-ionised water at room temperature for 3 hours. The optical density of the image is measured using a Macbeth 1200 series Densitometer before and after immersion.
Heat and Moisture Resistance of Image: This test assesses the effects of heat and moisture on the image.
An image is produced using an Atlantek thermal response tester model 200. The image is aged at 60 C at 70% R.H. for 24 hours. The optical density of the image is measured using a Macbeth 1200 series Densitometer before and after exposure.
Claims (6)
1. A heat sensitive composition comprising a] a colour former compound b] a developer c] a stabiliser of formula (1) J (1) COOR wherein R stands for hydrogen, C,-C8alkyl, C2-C8alkenyl, C6-C,0aryl, aralkyl having seven to ten carbon atoms, aroyl, wherein aryl has 6 to 10 carbon atoms, and wherein aryl, aralkyl and aroyl radicals may be substituted one, two or three times by C,-C4alkyl, C,-C4alkoxy, or halogen, R. stands for C,C8alkyl, C2-C8alkenyl or C3-C,0cycloalkyl, R2 stands for C,-C8alkyl or C6C,0aryl, which may be substituted one, two or three times by C,-C8alkyl, C,-C8alkoxy, or halogen.
2. A heat sensitive composition according to claim 1, wherein the heat sensitive composition comprises a sensitiser.
3. A heat sensitive composition according to claims 1 or 2, wherein as colour former compound a monophase solid solution comprising at least two colour former compounds is used.
4. A heat sensitive composition according to any one of claims 1 to 3, wherein the weightratio of compound of formula (1) to colour former is chosen in the range of 0.05:1. 0 to 1.0:1.0.
- 22
5. Heat sensitive recording material comprising the heat sensitive composition of claims 1 to 4 and a substrate.
6. Use of compound of formula (1) R' R' JJ ( 1)
R2, R2
COOR wherein R stands for hydrogen, C'-C8alkyl, C2-C8alkenyl, C6-C,0aryl, aralkyl having seven to ten carbon atoms, aroyl, wherein aryl has 6 to 10 carbon atoms, and wherein aryl, aralkyl and aroyl radicals may be substituted one, two or three times by C,-C4alkyl, C,-C4alkoxy, or halogen, R. stands for C,-C8alkyl, C2-C8alkenyl or C3-C,0cycloalkyl, R2 stands for C,-C8alkyl or C6-C,0aryl, which may be substituted one, two or three times by C,-C8alkyl, C,-C8alkoxy, or halogen, as stabiliser in heat sensitive compositions and heat sensitive recording materials.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0227205A GB0227205D0 (en) | 2002-11-20 | 2002-11-20 | Heat sensitive composition comprising benzoic acid derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB0326306D0 GB0326306D0 (en) | 2003-12-17 |
| GB2395569A true GB2395569A (en) | 2004-05-26 |
Family
ID=9948282
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB0227205A Ceased GB0227205D0 (en) | 2002-11-20 | 2002-11-20 | Heat sensitive composition comprising benzoic acid derivatives |
| GB0326306A Withdrawn GB2395569A (en) | 2002-11-20 | 2003-11-11 | Heat sensitive compositions comprising benzoic acid derivatives. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB0227205A Ceased GB0227205D0 (en) | 2002-11-20 | 2002-11-20 | Heat sensitive composition comprising benzoic acid derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (2) | GB0227205D0 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007013471A1 (en) * | 2005-07-25 | 2007-02-01 | Tokyo Ohka Kogyo Co., Ltd. | Compounds, process for production thereof, low-molecular compounds, positive resist compositions and process for formation of resist patterns |
-
2002
- 2002-11-20 GB GB0227205A patent/GB0227205D0/en not_active Ceased
-
2003
- 2003-11-11 GB GB0326306A patent/GB2395569A/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007013471A1 (en) * | 2005-07-25 | 2007-02-01 | Tokyo Ohka Kogyo Co., Ltd. | Compounds, process for production thereof, low-molecular compounds, positive resist compositions and process for formation of resist patterns |
Also Published As
| Publication number | Publication date |
|---|---|
| GB0326306D0 (en) | 2003-12-17 |
| GB0227205D0 (en) | 2002-12-24 |
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|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |