JP6869344B2 - 記録材料及び化合物 - Google Patents
記録材料及び化合物 Download PDFInfo
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- JP6869344B2 JP6869344B2 JP2019523513A JP2019523513A JP6869344B2 JP 6869344 B2 JP6869344 B2 JP 6869344B2 JP 2019523513 A JP2019523513 A JP 2019523513A JP 2019523513 A JP2019523513 A JP 2019523513A JP 6869344 B2 JP6869344 B2 JP 6869344B2
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- 150000001875 compounds Chemical class 0.000 title claims description 60
- 239000000463 material Substances 0.000 title claims description 31
- 125000004122 cyclic group Chemical group 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 26
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- -1 urea urethane compound Chemical class 0.000 description 80
- 239000007788 liquid Substances 0.000 description 28
- 239000000975 dye Substances 0.000 description 26
- 239000006185 dispersion Substances 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- 238000012360 testing method Methods 0.000 description 22
- 238000011156 evaluation Methods 0.000 description 21
- 239000013078 crystal Substances 0.000 description 20
- 238000011161 development Methods 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 150000003457 sulfones Chemical class 0.000 description 17
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 16
- 239000012964 benzotriazole Substances 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 15
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 15
- 239000010410 layer Substances 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 14
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- NSMMFSKPGXCMOE-UHFFFAOYSA-N 2-[2-(2-sulfophenyl)ethenyl]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=CC1=CC=CC=C1S(O)(=O)=O NSMMFSKPGXCMOE-UHFFFAOYSA-N 0.000 description 11
- 229920002451 polyvinyl alcohol Polymers 0.000 description 11
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000004372 Polyvinyl alcohol Substances 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000945 filler Substances 0.000 description 9
- 239000005995 Aluminium silicate Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 235000012211 aluminium silicate Nutrition 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 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 7
- 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 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Chemical class 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-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
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 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 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000006096 absorbing agent Substances 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
- 239000004611 light stabiliser Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 4
- 229960004889 salicylic acid Drugs 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- JTWBMEAENZGSOQ-UHFFFAOYSA-N 1,2-bis(phenoxymethyl)benzene Chemical compound C=1C=CC=C(COC=2C=CC=CC=2)C=1COC1=CC=CC=C1 JTWBMEAENZGSOQ-UHFFFAOYSA-N 0.000 description 3
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical group C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 3
- SOTPAHSLPCKYOC-UHFFFAOYSA-N 1-(2-hydroxyphenyl)-3-phenylurea Chemical compound OC1=CC=CC=C1NC(=O)NC1=CC=CC=C1 SOTPAHSLPCKYOC-UHFFFAOYSA-N 0.000 description 3
- YYUJEEGDLCZLSE-UHFFFAOYSA-N 1-(3-hydroxyphenyl)-3-phenylurea Chemical compound OC1=CC=CC(NC(=O)NC=2C=CC=CC=2)=C1 YYUJEEGDLCZLSE-UHFFFAOYSA-N 0.000 description 3
- OAGNKYSIOSDNIG-UHFFFAOYSA-N 1-methyl-3-[2-(3-methylphenoxy)ethoxy]benzene Chemical compound CC1=CC=CC(OCCOC=2C=C(C)C=CC=2)=C1 OAGNKYSIOSDNIG-UHFFFAOYSA-N 0.000 description 3
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 3
- WLTCCDHHWYAMCG-UHFFFAOYSA-N 2-phenylmethoxynaphthalene Chemical compound C=1C=C2C=CC=CC2=CC=1OCC1=CC=CC=C1 WLTCCDHHWYAMCG-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 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 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920002125 Sokalan® Polymers 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 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 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 238000011981 development test Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 3
- 239000003094 microcapsule Substances 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 239000004584 polyacrylic acid Substances 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- QCZZSANNLWPGEA-UHFFFAOYSA-N 1-(4-phenylphenyl)ethanone Chemical group C1=CC(C(=O)C)=CC=C1C1=CC=CC=C1 QCZZSANNLWPGEA-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
- 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
- LROZSPADHSXFJA-UHFFFAOYSA-N 2-(4-hydroxyphenyl)sulfonylphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=CC=C1O LROZSPADHSXFJA-UHFFFAOYSA-N 0.000 description 2
- WXHVQMGINBSVAY-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 WXHVQMGINBSVAY-UHFFFAOYSA-N 0.000 description 2
- QKJAZPHKNWSXDF-UHFFFAOYSA-N 2-bromoquinoline Chemical compound C1=CC=CC2=NC(Br)=CC=C21 QKJAZPHKNWSXDF-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- XCSGHNKDXGYELG-UHFFFAOYSA-N 2-phenoxyethoxybenzene Chemical compound C=1C=CC=CC=1OCCOC1=CC=CC=C1 XCSGHNKDXGYELG-UHFFFAOYSA-N 0.000 description 2
- PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 description 2
- LZHCVNIARUXHAL-UHFFFAOYSA-N 2-tert-butyl-4-ethylphenol Chemical compound CCC1=CC=C(O)C(C(C)(C)C)=C1 LZHCVNIARUXHAL-UHFFFAOYSA-N 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
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- PRWJPWSKLXYEPD-UHFFFAOYSA-N 4-[4,4-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butan-2-yl]-2-tert-butyl-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(C)CC(C=1C(=CC(O)=C(C=1)C(C)(C)C)C)C1=CC(C(C)(C)C)=C(O)C=C1C PRWJPWSKLXYEPD-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- AJWUMVPXWNNESR-UHFFFAOYSA-N 6-n,6-n-diethyl-2-n-fluoro-3-methyloctane-2,6-diamine Chemical compound CCN(CC)C(CC)CCC(C)C(C)NF AJWUMVPXWNNESR-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
- 239000004215 Carbon black (E152) Substances 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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- ZKURGBYDCVNWKH-UHFFFAOYSA-N [3,7-bis(dimethylamino)phenothiazin-10-yl]-phenylmethanone Chemical compound C12=CC=C(N(C)C)C=C2SC2=CC(N(C)C)=CC=C2N1C(=O)C1=CC=CC=C1 ZKURGBYDCVNWKH-UHFFFAOYSA-N 0.000 description 2
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- 230000000181 anti-adherent effect Effects 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
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- 238000002076 thermal analysis method Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- B41M5/323—Organic colour formers, e.g. leuco dyes
-
- 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
-
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Description
本願は、2017年6月8日に出願された日本国特許出願第2017−113439号に対し優先権を主張し、その内容をここに援用する。
ジフェニルウレア構造を有する非フェノール系顕色剤は既に知られている。ジフェニルウレア自体(特許文献1参照)は発色性能に難があるが、顕色剤としての性能が改善された関連化合物として、特許文献2に記載されているウレアウレタン化合物、特許文献3又は4に記載されているジフェニルウレア構造とスルホンアミド構造を有する化合物等がある。
また関連化合物として、特許文献5や非特許文献1〜3に記載されたものがあるが、これらの用途としては医薬(抗動脈硬化剤あるいは抗有糸***剤)が知られるのみであり、記録材料用途は知られていない。
本発明者は、発色性能に優れた非フェノール系顕色剤につき更に探索を行った。
(1)発色性染料を含有する記録材料において、下記式(I)
R1〜R3は、それぞれ独立して、水素原子、ハロゲン原子、ニトロ基、シアノ基、直鎖、分岐もしくは環状のC1〜C6アルキルカルボニル基、直鎖、分岐もしくは環状のC1〜C6アルキル基、直鎖、分岐もしくは環状のC1〜C6アルコキシ基、C2〜C6アルケニル基、直鎖、分岐もしくは環状のC1〜C6フルオロアルキル基、N(R4)2基(式中、R4は水素原子、フェニル基、ベンジル基、又は直鎖、分岐もしくは環状のC1〜C6アルキル基を表す)、NHCOR5基(式中、R5は直鎖、分岐もしくは環状のC1〜C6アルキル基を表す)、置換されていてもよいフェニル基、又は置換されていてもよいベンジル基を表し、
n1及びn3は、それぞれ独立して、1〜5のいずれかの整数を表し、
ベンゼン環上の隣接するR3で表される基の2個が結合して、置換されていてもよい6員環を形成してもよく、
n2は1〜4のいずれかの整数を表す。)
で表される化合物からなる群から選ばれる少なくとも1種を含有することを特徴とする記録材料。
(2)支持体上に、(1)に記載の記録材料から形成されてなる記録材料層を有する記録シート。
(3)下記式(I)
R1〜R3は、それぞれ独立して、水素原子、ハロゲン原子、ニトロ基、シアノ基、直鎖、分岐もしくは環状のC1〜C6アルキルカルボニル基、直鎖、分岐もしくは環状のC1〜C6アルキル基、直鎖、分岐もしくは環状のC1〜C6アルコキシ基、C2〜C6アルケニル基、直鎖、分岐もしくは環状のC1〜C6フルオロアルキル基、N(R4)2基(式中、R4は水素原子、フェニル基、ベンジル基、又は直鎖、分岐もしくは環状のC1〜C6アルキル基を表す)、NHCOR5基(式中、R5は直鎖、分岐もしくは環状のC1〜C6アルキル基を表す)、置換されていてもよいフェニル基、又は置換されていてもよいベンジル基を表し、
n1及びn3は、それぞれ独立して、1〜5のいずれかの整数を表し、
ベンゼン環上の隣接するR3で表される基の2個が結合して、置換されていてもよい6員環を形成してもよく、
n2は1〜4のいずれかの整数を表す。)
で表される化合物からなる群から選ばれる少なくとも1種を顕色剤に用いる方法。
(4)下記式(I)
R1〜R3は、それぞれ独立して、水素原子、ハロゲン原子、ニトロ基、シアノ基、直鎖、分岐もしくは環状のC1〜C6アルキルカルボニル基、直鎖、分岐もしくは環状のC1〜C6アルキル基、直鎖、分岐もしくは環状のC1〜C6アルコキシ基、C2〜C6アルケニル基、直鎖、分岐もしくは環状のC1〜C6フルオロアルキル基、N(R4)2基(式中、R4は水素原子、フェニル基、ベンジル基、又は直鎖、分岐もしくは環状のC1〜C6アルキル基を表す)、NHCOR5基(式中、R5は直鎖、分岐もしくは環状のC1〜C6アルキル基を表す)、置換されていてもよいフェニル基、又は置換されていてもよいベンジル基を表し、
n1及びn3は、それぞれ独立して、1〜5のいずれかの整数を表し、
ベンゼン環上の隣接するR3で表される基の2個が結合して、置換されていてもよい6員環を形成してもよく、
n2は1〜4のいずれかの整数を表す。)
で表される化合物。
式(I)中、Xは、CH2、C=O、又はSO2を表す。
これらのうち、式(III)で表される化合物が、発色性等の性能の点で好ましい。
特に、X=COである場合には、式(III)又は式(IV)で表される化合物が好ましく、式(III)で表される化合物がさらに好ましい。またX=SO2である場合には、式(III)で表される化合物が好ましい。
水素原子;
フッ素原子、塩素原子、臭素原子、ヨウ素原子等のハロゲン原子;
ニトロ基;
シアノ基;
メチル、エチル、プロピル、イソプロピル、n−ブチル、イソブチル、sec−ブチル、t−ブチル、n−ペンチル、イソペンチル、ネオペンチル、n−ヘキシル、イソヘキシル、シクロプロピル、シクロブチル、2−メチルシクロプロピル、シクロプロピルメチル、シクロペンチル、シクロヘキシル等の直鎖、分岐もしくは環状のC1〜C6アルキル基;メトキシ、エトキシ、プロポキシ、イソプロポキシ、n−ブトキシ、イソブトキシ、sec−ブトキシ、t−ブトキシ、n−ペンチルオキシ、イソペンチルオキシ、n−ヘキシルオキシ、シクロプロポキシ、シクロブトキシ、2−メチルシクロプロポキシ、シクロプロピルメトキシ、シクロペンチルオキシ、シクロヘキシルオキシ等の直鎖、分岐もしくは環状のC1〜C6アルコキシ基;
メチルカルボニル、エチルカルボニル、プロピルカルボニル、イソプロピルカルボニル、n−ブチルカルボニル、イソブチルカルボニル、sec−ブチルカルボニル、t−ブチルカルボニル、n−ペンチルカルボニル、イソペンチルカルボニル、ネオペンチルカルボニル、n−ヘキシルカルボニル、イソヘキシルカルボニル、シクロプロピルカルボニル、シクロブチルカルボニル、2−メチルシクロプロピルカルボニル、シクロプロピルメチルカルボニル、シクロペンチルカルボニル、シクロヘキシルカルボニル等の直鎖、分岐もしくは環状のC1〜C6アルキルカルボニル基;
ビニル基、アリル基、イソプロペニル基、1−プロペニル基、2−プロペニル基、1−ブテニル基、2−ブテニル基、3−ブテニル基、1,3−ブタンジエニル基、又は2−メチル−2−プロペニル基等のC2〜C6アルケニル基;
トリフルオロメチル基、パーフルオロエチル基、パーフルオロプロピル基、パーフルオロブチル基、パーフルオロヘキシル基、パーフルオロシクロヘキシル基等の直鎖、分岐もしくは環状のC1〜C6フルオロアルキル基;
N(R4)2基(R4は水素原子、フェニル基、ベンジル基、又は直鎖、分岐もしくは環状のC1〜C6アルキル基を表す);
NHCOR5(R5は直鎖、分岐もしくは環状のC1〜C6アルキル基を表す);
置換されていてもよいフェニル基;
置換されていてもよいベンジル基等を挙げることができる。
また、R3がベンゼン環上で隣接する位置に少なくとも2個存在する場合には、これらの隣接するR3の2個が互いに結合して、それらが直接結合している前記ベンゼン環の炭素原子とともに、置換されていてもよい6員環を形成してもよい。具体的には、隣接するR3の2個が互いに結合して、置換されていてもよい1,3−ジブテン−1,4−イル基を形成することにより、前記ベンゼン環と共にナフタレン環(Xとの結合位置は1位又は2位のいずれかである。)を形成してなる化合物;
隣接するR3の2個が互いに結合して、置換されていてもよい1−ブテン−1,4−イル基を形成することにより、前記ベンゼン環と共に1,2−ジヒドロナフタレン環(Xとの結合位置は5位、6位、7位又は8位のいずれかである。)を形成してなる化合物;隣接するR3の2個が互いに結合して、置換されていてもよい2−ブテン−1,4−イル基を形成することにより、前記ベンゼン環と共に1,4−ジヒドロナフタレン環(Xとの結合位置は5位又は6位のいずれかである。)を形成してなる化合物;
隣接するR3の2個が互いに結合して、置換されていてもよいブタン−1,4−イル基を形成することにより、前記ベンゼン環と共にテトラリン環(Xとの結合位置は1位又は2位のいずれかである。)を形成してなる化合物;が例示される。
好ましくは、R1としては、水素原子、直鎖状のC1〜C6アルキル基、直鎖状のC1〜C6アルコキシ基、塩素原子またはニトロ基であり、R2としては、水素原子であり、R3としては、水素原子又は直鎖状のC1〜C6アルキル基である。
ここで、「置換されていてもよい」の置換基として、
フッ素原子、塩素原子、臭素原子、ヨウ素原子等のハロゲン原子;
メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、sec−ブチル基、t−ブチル基、n−ペンチル基、イソペンチル基、ネオペンチル基、t−ペンチル基、n−ヘキシル基、イソヘキシル基、1−メチルペンチル基、2−メチルペンチル基等のC1〜C6アルキル基;
メトキシ基、エトキシ基、n−プロポキシ基、イソプロポキシ基、n−ブトキシ基、sec−ブトキシ基、t−ブトキシ基等のC1〜C6のアルコキシ基等を挙げることができる。
式(I)で表される化合物は、製造可能であればどのような方法でも構わないが、公知の種々の方法、例えば下記に示す製造方法1〜4のいずれかで製造することができる。
式(I)で表される化合物は、一般式(V)
さらに、XがCH2である場合には、式(I)で表される化合物は、下記(1)及び(2)の工程を経て製造することもできる。
(1)一般式(VII)
(2)前記式(IX)で表されるフェノール誘導体と、一般式(X)
さらに、XがC=Oである場合には、式(I)で表される化合物は、製造方法2と同じ(1)工程の後、下記の(2’)工程を経て、製造することもできる。
(2’)前記式(IX)で表されるフェノール誘導体と、一般式(XI)
さらに、XがSO2である場合には、式(I)で表される化合物は、製造方法2と同じ(1)工程の後、下記の(2’’)工程を経て、製造することもできる。
(2’’)前記式(IX)で表されるフェノール誘導体と、一般式(XIII)
また、以上のようにして合成することができる化合物の一例を第1表に示す。
本発明の記録材料は発色性染料と式(I)で表される化合物の少なくとも1種とを含有する記録材料であればどの様な用途にも使用でき、例えば、感熱記録材料又は感圧複写材料等に利用することができる。
本発明の記録材料の中には、発色性染料並びに、式(I)で表される化合物以外に公知の顕色剤、画像安定剤、増感剤、填料、分散剤、酸化防止剤、減感剤、粘着防止剤、消泡剤、光安定剤、蛍光増白剤等を必要に応じ1種又は2種以上含有させることができる。他の成分の使用量は、それぞれ、発色性染料1質量部に対して、通常0.1〜15質量部、好ましくは1〜10質量部の範囲である。
ビスフェノールA、4,4’−sec−ブチリデンビスフェノール、4,4’−シクロヘキシリデンビスフェノール、2,2’−ビス(4−ヒドロキシフェニル)−3,3’−ジメチルブタン、2,2’−ジヒドロキシジフェニル、ペンタメチレン−ビス(4−ヒドロキシベンゾエート)、2,2−ジメチル−3,3−ジ(4−ヒドロキシフェニル)ペンタン、2,2−ジ(4−ヒドロキシフェニル)ヘキサン、2,2−ビス(4−ヒドロキシフェニル)プロパン、2,2−ビス(4−ヒドロキシフェニル)ブタン、2,2−ビス(4−ヒドロキシ−3−メチルフェニル)プロパン、4,4’−(1−フェニルエチリデン)ビスフェノール、4,4’−エチリデンビスフェノール、(ヒドロキシフェニル)メチルフェノール、2,2’−ビス(4−ヒドロキシ−3−フェニル−フェニル)プロパン、4,4’−(1,3−フェニレンジイソプロピリデン)ビスフェノール、4,4’−(1,4−フェニレンジイソプロピリデン)ビスフェノール、2,2−ビス(4−ヒドロキシフェニル)酢酸ブチル等のビスフェノール化合物;4,4’−ジヒドロキシジフェニルチオエーテル、1,7−ジ(4−ヒドロキシフェニルチオ)−3,5−ジオキサヘプタン、2,2’−ビス(4−ヒドロキシフェニルチオ)ジエチルエーテル、4,4’−ジヒドロキシ−3,3’−ジメチルジフェニルチオエーテル等の含硫黄ビスフェノール化合物;4−ヒドロキシ安息香酸ベンジル、4−ヒドロキシ安息香酸エチル、4−ヒドロキシ安息香酸プロピル、4−ヒドロキシ安息香酸イソプロピル、4−ヒドロキシ安息香酸ブチル、4−ヒドロキシ安息香酸イソブチル、4−ヒドロキシ安息香酸クロロベンジル、4−ヒドロキシ安息香酸メチルベンジル、4−ヒドロキシ安息香酸ジフェニルメチル等の4−ヒドロキシ安息香酸エステル類;安息香酸亜鉛、4−ニトロ安息香酸亜鉛等の安息香酸金属塩、4−[2−(4−メトキシフェニルオキシ)エチルオキシ]サリチル酸等のサリチル酸類;サリチル酸亜鉛、ビス[4−(オクチルオキシカルボニルアミノ)−2−ヒドロキシ安息香酸]亜鉛等のサリチル酸金属塩;4,4’−ジヒドロキシジフェニルスルホン(略称:4,4’−BPS)、2,4’−ジヒドロキシジフェニルスルホン、4−ヒドロキシ−4’−メチルジフェニルスルホン、4−ヒドロキシ−4’−イソプロポキシジフェニルスルホン、4−ヒドロキシ−4’−ブトキシジフェニルスルホン、4,4’−ジヒドロキシ−3,3’−ジアリルジフェニルスルホン、3,4−ジヒドロキシ−4’−メチルジフェニルスルホン、4,4’−ジヒドロキシ−3,3’,5,5’−テトラブロモジフェニルスルホン、4−アリルオキシ−4’−ヒドロキシジフェニルスルホン、2−(4−ヒドロキシフェニルスルホニル)フェノール、4,4’−スルホニルビス[2−(2−プロペニル)]フェノール、4−[{4−(プロポキシ)フェニル}スルホニル]フェノール、4−[{4−(アリロキシ)フェニル}スルホニル]フェノール、4−[{4−(ベンジロキシ)フェニル}スルホニル]フェノール、2,4−ビス(フェニルスルホニル)−5−メチル−フェノール等のヒドロキシスルホン類;4−フェニルスルホニルフェノキシ亜鉛マグネシウム、アルミニウム、チタン等のヒドロキシスルホン類の多価金属塩類;4−ヒドロキシフタル酸ジメチル、4−ヒドロキシフタル酸ジシクロヘキシル、4−ヒドロキシフタル酸ジフェニル等の4−ヒドロキシフタル酸ジエステル類;2−ヒドロキシ−6−カルボキシナフタレン等のヒドロキシナフトエ酸のエステル類;トリブロモメチルフェニルスルホン等のトリハロメチルスルホン類;N−フェニル−4−アミノベンゼンスルホンアミド、N−フェニル−3−ニトロベンゼンスルホンアミド、N−(2−メトキシフェニル)−p−トルエンスルホンアミド、ネオウリロン等のスルホンアミド化合物;1,2−ジフェニルウレア、N−フェニル−4−(3−フェニルウレイド)ベンゼンスルホンアミド、4−メチル−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、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、N−(2−(3−フェニルウレイド)フェニル)アセトアミド、4−メチル−N−(2−(3−フェニルウレイド)フェニル)ベンズアミド等のジフェニルウレア化合物;4,4’−ビス(p−トルエンスルホニルアミノカルボニルアミノ)ジフェニルメタン、N−(4−メチルフェニルスルホニル)−N’−(3−(4−メチルフェニルスルホニルオキシ)フェニル)ウレア(略称:PF−201)等のスルホニルウレア化合物;ヒドロキシアセトフェノン、p−フェニルフェノール、4−ヒドロキシフェニル酢酸ベンジル、p−ベンジルフェノール、ハイドロキノン−モノベンジルエーテル、2,4−ジヒドロキシ−2’−メトキシベンズアニリド、テトラシアノキノジメタン類、N−(2−ヒドロキシフェニル)−2−[(4−ヒドロキシフェニル)チオ]アセタミド、N−(4−ヒドロキシフェニル)−2−[(4−ヒドロキシフェニル)チオ]アセタミド、4−ヒドロキシベンゼンスルホンアニリド、4’−ヒドロキシ−4−メチルベンゼンスルホンアニリド、4,4’−ビス(4−メチル−3−フェノキシカルボニル)アミノフェニルウレイド))ジフェニルスルホン、3−(3−フェニルウレイド)ベンゼンスルホンアニリド、オクタデシルリン酸、ドデシルリン酸;又は下記式で表されるジフェニルスルホン架橋型化合物若しくはそれらの混合物等が挙げられる。
また、下記式で表されるジフェニルスルホン架橋型化合物若しくはそれらの混合物等が挙げられる。
分散剤は水、アルコール、ケトン、エステル、炭化水素等の溶剤に溶かして使用するほか、水又は他の溶媒中に乳化あるいはペースト状に分散させた状態で使用することも可能である。
本発明を感熱記録紙に使用する場合には、既知の使用方法と同様に行えばよく、例えば、本発明の化合物の微粒子及び発色性染料の微粒子のそれぞれをポリビニルアルコールやセルロース等の水溶性結合剤の水溶液中に分散された懸濁液を混合して紙等の支持体に塗布して乾燥することにより製造できる。
アンダーコート層分散液は、支持体の表面の平滑性を向上させるために用いるのであって、特に限定されるものではないが、填料、分散剤、水が含まれる方がよく、具体的には、填料としては焼成カオリン、炭酸カルシウム、分散剤としてはポリビニルアルコールが好ましい。
なお、焼成カオリンは、Ansilex(登録商標)−93を使用した。
(式(I)で表される化合物の製造方法)の項に記載した方法を用いて、各化合物を合成した。
[実施例1]1−(2−(ベンジルオキシ)フェニル)−3−フェニルウレア(化合物番号1)の合成
o−アミノフェノール10.9gをアセトニトリル200mlに加え、5℃まで冷却した。ここに、イソシアン酸フェニル(和光純薬社製、純度98%)11.9gを、温度が10℃以上にならないように滴下し、そのままの温度にて30分間反応を行った。反応終了後、析出した結晶をろ過し、白色結晶として1−(2−ヒドロキシフェニル)−3−フェニルウレアを得た(19.5g、収率85%)。
以上の方法で得られた1−(2−ヒドロキシフェニル)−3−フェニルウレア3.4g、及び10%水酸化ナトリウム水溶液7.0gをDMF15mlに加えた。ここに、室温にてベンジルクロリド2.1gを滴下した後、室温にて4時間反応を行い、更に60℃にて3時間反応を行った。反応終了後、室温に戻し、酢酸エチル50ml、及びn−ヘキサン20mlを加え、析出した結晶をろ過した。これを減圧下乾燥することにより、目的物を白色結晶として得た(2.2g、収率47%)。融点:172−173℃
実施例1と同様の方法で得られた合成中間体1−(2−ヒドロキシフェニル)−3−フェニルウレア3.0g、及びトリエチルアミン2.0gをアセトン50ml中に加えた。ここに40℃にてベンゾイルクロリド1.8gを滴下し、2時間反応を行った。反応終了後、不溶物をろ過にて取り除いた後に減圧下溶媒を留去した。残渣を66%エタノール75mlから再結晶を行った。析出した結晶をろ過し、減圧下乾燥させ、目的物を白色の結晶として得た(3.7g、収率98%)。融点:171−174℃
m−アミノフェノール10.9gをアセトニトリル200mlに加え、5℃まで冷却した。ここに、イソシアン酸フェニル11.9gを、温度が10℃以上にならないように滴下し、そのままの温度にて30分間反応を行った。反応終了後、析出した結晶をろ過し、白色結晶として1−(3−ヒドロキシフェニル)−3−フェニルウレアを得た(19.5g、収率85%)。
以上の方法で得られた1−(3−ヒドロキシフェニル)−3−フェニルウレア4.6g、及び炭酸カリウム1.4gをDMF20mlに加え、オイルバスにて90℃まで昇温した。ここに、ベンジルクロリド2.5gを滴下した後、90℃にて2時間反応を行った。反応終了後、1%塩酸100mlに反応液を滴下し、析出した結晶をろ過した。得られた結晶に酢酸エチル120mlを加え、還流下結晶を溶解した。n−ヘキサンを加え、室温まで冷却を行い、析出した結晶をろ過した。減圧下乾燥することにより、目的物を白色結晶として得た(3.7g、収率58%)。融点:179−182℃
実施例3と同様の方法で得られた合成中間体1−(3−ヒドロキシフェニル)−3−フェニルウレア4.6g、及びトリエチルアミン2.0gをアセトニトリル100ml中に加えた。ここに室温にてベンゾイルクロリド2.8gを滴下し、そのままの温度で1時間反応を行った。反応終了後、減圧下溶媒を留去し、残渣を酢酸エチル100mlに溶かし、5%塩酸100mlにて洗浄した。分液後、有機層を硫酸マグネシウムにて乾燥した。減圧下溶媒を留去し、残渣をアセトンから再結晶を行った。結晶をろ過し、減圧下乾燥させ、目的物を白色の結晶として得た(4.0g、収率60%)。融点:174−179℃
実施例3と同様の方法で得られた合成中間体1−(3−ヒドロキシフェニル)−3−フェニルウレア4.6g、及びトリエチルアミン2.1gをアセトン50ml中に加えた。ここに、p−トルエンスルホニルクロリド4.0gを加え、室温にて3時間反応した。反応終了後、反応液に1%塩酸を加え、析出した結晶をろ過した。得られた結晶を水で良く洗浄した後に、減圧下乾燥を行い、目的物を白色の結晶として得た(7.0g、収率91%)。融点:172−174℃
p−アミノフェノール5.5gを酢酸エチル50mlに加え、5℃まで冷却した。ここに、イソシアン酸フェニル6.0gを、温度が10℃以上にならないように滴下し、そのままの温度にて1時間反応を行った。反応終了後、析出した結晶をろ取し、アセトン100ml中に加えた。これに40℃にてベンゾイルクロリド7.0gを滴下し、30分間反応を行った。反応終了後、減圧下溶媒を留去し、目的物を白色の結晶として得た(12.6g、収率75%)。融点:215−216℃
1)感熱記録紙の作製
[評価サンプル3]
染料分散液(A液)
3−ジ−n−ブチルアミノ−6−メチル−7−アニリノフルオラン 16部
ポリビニルアルコール10%水溶液 84部
顕色剤分散液(B液)
化合物No.1(第1表参照) 16部
ポリビニルアルコール10%水溶液 84部
填料分散液(C液)
焼成カオリン 27.8部
ポリビニルアルコール10%水溶液 26.2部
水 71部
(部は質量部)
評価サンプル3の顕色剤分散液(B液)中、化合物No.1の代わりに第1表に示した各化合物を用いた以外は、評価サンプル3に記載の方法で感熱紙を作製した。なお、評価サンプル番号と顕色剤の関係を第2表に示した。
評価サンプル3の顕色剤分散液(B液)中、化合物No.1の代わりに、P−201(評価サンプル1)、又は4,4’−BPS(評価サンプル2)を用いた以外は、評価サンプル3に記載の方法で感熱紙を作製した。評価サンプル番号と顕色剤の関係を第2表に示した。
ここで、P−201は、N−p−トルエンスルホニル−N’−3−(p−トルエンスルホニルオキシフェニル)ウレアを、4,4‘−BPSは、4,4’−ジヒドロキシジフェニルスルホンを意味する。
評価サンプル1〜24で作製した感熱記録紙について、感熱紙発色試験装置(大倉電機製 TH−PMD型)を使用し、印字電圧17V、パルス幅1.8ms条件で市松模様に飽和発色させた。発色後の光学濃度を分光測色計(Spectroeye LT、X−rite社製)で測定した。その結果を第2表に示す。
評価サンプル1〜24に関して、試験前後の各試験紙について以下の各条件で保存性試験を行った。その結果を第3表にまとめて示した。
評価サンプル1〜24で作製した感熱記録紙の一部を切り取り、地肌の光学濃度を分光測色計(Spectroeye LT、X−rite社製)で測定した。その結果を第3表に示す。
評価サンプル1〜24で作製した感熱記録紙の一部を切り取り、恒温器(商品名:DK−400、YAMATO製)中で温度100℃で24時間保持した。保持した後の地肌の光学濃度を分光測色計(Spectroeye LT、X−rite社製)で測定した。その結果を第3表に示す。
評価サンプル1、2、8、11〜13、15、17〜21、23に関して、各試験紙について以下の条件で保存性試験を行った。その結果から判定した評価を第4表にまとめて示した。
評価サンプル1、2、8、11〜13、15、17〜21、23で作製した感熱記録紙の一部を切り取り、感熱紙発色試験装置(商品名:TH−PMH型、大倉電機製)を使用し、印字電圧17V、パルス幅1.8msの条件で発色させ、発色画像濃度を分光測色計(Spectroeye LT、X−rite社製)で測定した。その結果を第4表に示す。
評価サンプル1、2、8、11〜13、15、17〜21、23で作製した感熱記録紙の一部を切り取り、試験前と同様にして飽和発色させた。次いで、各試験紙を恒温器(商品名:DK−400、YAMATO製)中で温度100℃で24時間保持した。保持した後の地肌の光学濃度を分光測色計(Spectroeye LT、X−rite社製)で測定した。その結果を第4表に示す。
評価サンプル1、2、8、11〜13、15、17〜21、23で作製した感熱記録紙の一部を切り取り、試験前と同様にして飽和発色させた。次いで、各試験紙の発色面及び裏面に塩化ビニルラップフィルム(可塑剤が含まれているもの)を密着させ、その状態のまま、40℃で4時間保持した。試験後の光学濃度を分光測色計(Spectroeye
LT、X−rite社製)で測定した。その結果を第4表に示す。
評価サンプル1、2、8、11〜13、15、17〜21、23で作製した感熱記録紙の一部を切り取り、試験前と同様にして飽和発色させた。次いで、各試験紙を、35%エタノール溶液に25℃で1時間、浸漬させた。試験後の光学濃度を分光測色計(Spectroeye LT、X−rite社製)で測定した。その結果を第4表に示す。
Claims (4)
- 発色性染料を含有する記録材料において、下記式(I)
R1〜R3は、それぞれ独立して、水素原子、ハロゲン原子、ニトロ基、シアノ基、直鎖、分岐もしくは環状のC1〜C6アルキルカルボニル基、直鎖、分岐もしくは環状のC1〜C6アルキル基、直鎖、分岐もしくは環状のC1〜C6アルコキシ基、C2〜C6アルケニル基、直鎖、分岐もしくは環状のC1〜C6フルオロアルキル基、N(R4)2基(式中、R4は水素原子、フェニル基、ベンジル基、又は直鎖、分岐もしくは環状のC1〜C6アルキル基を表す)、NHCOR5基(式中、R5は直鎖、分岐もしくは環状のC1〜C6アルキル基を表す)、置換されていてもよいフェニル基、又は置換されていてもよいベンジル基を表し、
n1及びn3は、それぞれ独立して、1〜5のいずれかの整数を表し、
ベンゼン環上の隣接するR3で表される基の2個が結合して、置換されていてもよい6員環を形成してもよく、
n2は1〜4のいずれかの整数を表す。
ただし、XがSO 2 又はC=Oの場合は、R 1 及びR 2 はいずれも水素原子である場合を除く)
で表される化合物からなる群から選ばれる少なくとも1種を含有することを特徴とする記録材料。 - 支持体上に、請求項1に記載の記録材料から形成されてなる記録材料層を有する記録シート。
- 下記式(I)
R1〜R3は、それぞれ独立して、水素原子、ハロゲン原子、ニトロ基、シアノ基、直鎖、分岐もしくは環状のC1〜C6アルキルカルボニル基、直鎖、分岐もしくは環状のC1〜C6アルキル基、直鎖、分岐もしくは環状のC1〜C6アルコキシ基、C2〜C6アルケニル基、直鎖、分岐もしくは環状のC1〜C6フルオロアルキル基、N(R4)2基(式中、R4は水素原子、フェニル基、ベンジル基、又は直鎖、分岐もしくは環状のC1〜C6アルキル基を表す)、NHCOR5基(式中、R5は直鎖、分岐もしくは環状のC1〜C6アルキル基を表す)、置換されていてもよいフェニル基、又は置換されていてもよいベンジル基を表し、
n1及びn3は、それぞれ独立して、1〜5のいずれかの整数を表し、
ベンゼン環上の隣接するR3で表される基の2個が結合して、置換されていてもよい6員環を形成してもよく、
n2は1〜4のいずれかの整数を表す。
ただし、XがSO 2 又はC=Oの場合は、R 1 及びR 2 はいずれも水素原子である場合を除く)
で表される化合物からなる群から選ばれる少なくとも1種を顕色剤に用いる方法。 - 下記式(I)
R1〜R3は、それぞれ独立して、水素原子、ハロゲン原子、直鎖、分岐もしくは環状のC1〜C6アルキル基、直鎖、分岐もしくは環状のC1〜C6アルコキシ基、C2〜C6アルケニル基、直鎖、分岐もしくは環状のC1〜C6フルオロアルキル基、N(R4)2基(式中、R4は水素原子、フェニル基、ベンジル基、又は直鎖、分岐もしくは環状のC1〜C6アルキル基を表す)、NHCOR5基(式中、R5は直鎖、分岐もしくは環状のC1〜C6アルキル基を表す)、フェニル基、又はベンジル基を表し、
n1及びn3は、それぞれ独立して、1〜5のいずれかの整数を表し、
ベンゼン環上の隣接するR3で表される基の2個が結合して、前記ベンゼン環と共にナフタレン環を形成してもよく、
n2は1〜4のいずれかの整数を表す。
ただし、XがSO 2 又はC=Oの場合は、R 1 及びR 2 はいずれも水素原子である場合を除く)
で表される化合物。
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