JP6968434B2 - N,n’−ジアリール尿素誘導体及びその製造方法、並びに、それを用いた感熱記録材料 - Google Patents
N,n’−ジアリール尿素誘導体及びその製造方法、並びに、それを用いた感熱記録材料 Download PDFInfo
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- JP6968434B2 JP6968434B2 JP2019051776A JP2019051776A JP6968434B2 JP 6968434 B2 JP6968434 B2 JP 6968434B2 JP 2019051776 A JP2019051776 A JP 2019051776A JP 2019051776 A JP2019051776 A JP 2019051776A JP 6968434 B2 JP6968434 B2 JP 6968434B2
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- divalent
- hydrogen atoms
- bis
- phenyl
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- 229910052757 nitrogen Inorganic materials 0.000 title claims description 73
- 239000000463 material Substances 0.000 title claims description 54
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- -1 monocyclic aromatic hydrocarbon Chemical class 0.000 claims description 142
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 91
- 150000001875 compounds Chemical class 0.000 claims description 50
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 26
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 claims description 26
- 229920006395 saturated elastomer Polymers 0.000 claims description 25
- 229930195733 hydrocarbon Natural products 0.000 claims description 17
- 239000004215 Carbon black (E152) Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 10
- 239000000975 dye Substances 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 239000000981 basic dye Substances 0.000 claims description 9
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 7
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 150000003459 sulfonic acid esters Chemical class 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- QRWVOJLTHSRPOA-UHFFFAOYSA-N 1,3-bis(prop-2-enyl)urea Chemical class C=CCNC(=O)NCC=C QRWVOJLTHSRPOA-UHFFFAOYSA-N 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 description 73
- 238000003786 synthesis reaction Methods 0.000 description 73
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 66
- 239000010410 layer Substances 0.000 description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 43
- 238000012360 testing method Methods 0.000 description 38
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 30
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 23
- 229920005989 resin Polymers 0.000 description 21
- 239000011347 resin Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- CVBQNEVAKTZFTD-UHFFFAOYSA-N bis[3-[[3-(4-methylphenyl)sulfonyloxyphenyl]carbamoylamino]phenyl] benzene-1,3-disulfonate Chemical compound CC1=CC=C(C=C1)S(=O)(=O)OC2=CC=CC(=C2)NC(=O)NC3=CC(=CC=C3)OS(=O)(=O)C4=CC(=CC=C4)S(=O)(=O)OC5=CC=CC(=C5)NC(=O)NC6=CC(=CC=C6)OS(=O)(=O)C7=CC=C(C=C7)C CVBQNEVAKTZFTD-UHFFFAOYSA-N 0.000 description 19
- 229920002451 polyvinyl alcohol Polymers 0.000 description 19
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000004372 Polyvinyl alcohol Substances 0.000 description 17
- 238000000576 coating method Methods 0.000 description 17
- 238000003860 storage Methods 0.000 description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 16
- 239000011230 binding agent Substances 0.000 description 15
- 239000011248 coating agent Substances 0.000 description 14
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 14
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000003973 paint Substances 0.000 description 12
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- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
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- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 8
- 235000010290 biphenyl Nutrition 0.000 description 8
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
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- 239000001023 inorganic pigment Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000012752 auxiliary agent Substances 0.000 description 6
- ALIQZUMMPOYCIS-UHFFFAOYSA-N benzene-1,3-disulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC(S(Cl)(=O)=O)=C1 ALIQZUMMPOYCIS-UHFFFAOYSA-N 0.000 description 6
- 238000011161 development Methods 0.000 description 6
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- 229920000126 latex Polymers 0.000 description 6
- 239000004816 latex Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000012860 organic pigment Substances 0.000 description 6
- 235000019698 starch Nutrition 0.000 description 6
- BBQLCKFJEDETJU-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-phenylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1=CC=CC=C1 BBQLCKFJEDETJU-UHFFFAOYSA-N 0.000 description 5
- 239000005995 Aluminium silicate Substances 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 235000012211 aluminium silicate Nutrition 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 5
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- 239000011241 protective layer Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 150000003457 sulfones Chemical class 0.000 description 5
- 239000008096 xylene 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 4
- XLOFWIXHLWXUQN-UHFFFAOYSA-N bis[3-[[3-(4-methylphenyl)sulfonyloxyphenyl]carbamoylamino]phenyl] benzene-1,3-dicarboxylate Chemical compound CC1=CC=C(C=C1)S(=O)(=O)OC2=CC=CC(=C2)NC(=O)NC3=CC(=CC=C3)OC(=O)C4=CC(=CC=C4)C(=O)OC5=CC=CC(=C5)NC(=O)NC6=CC(=CC=C6)OS(=O)(=O)C7=CC=C(C=C7)C XLOFWIXHLWXUQN-UHFFFAOYSA-N 0.000 description 4
- MFGZXPGKKJMZIY-UHFFFAOYSA-N ethyl 5-amino-1-(4-sulfamoylphenyl)pyrazole-4-carboxylate Chemical compound NC1=C(C(=O)OCC)C=NN1C1=CC=C(S(N)(=O)=O)C=C1 MFGZXPGKKJMZIY-UHFFFAOYSA-N 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
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- RUTYWCZSEBLPAK-UHFFFAOYSA-N (4-methylphenyl)sulfonylurea Chemical compound CC1=CC=C(S(=O)(=O)NC(N)=O)C=C1 RUTYWCZSEBLPAK-UHFFFAOYSA-N 0.000 description 3
- XCSGHNKDXGYELG-UHFFFAOYSA-N 2-phenoxyethoxybenzene Chemical compound C=1C=CC=CC=1OCCOC1=CC=CC=C1 XCSGHNKDXGYELG-UHFFFAOYSA-N 0.000 description 3
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 3
- 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
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- 0 C[C@@](CCC1)(C(*)(*)OCCOCCO*CCC=CC=S)C=CC1[N+]([O-])=O Chemical compound C[C@@](CCC1)(C(*)(*)OCCOCCO*CCC=CC=S)C=CC1[N+]([O-])=O 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
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- XPNPQJYPKUUKRI-UHFFFAOYSA-N [3-[[3-[3-[3-[(3-acetyloxyphenyl)carbamoylamino]phenoxy]sulfonylphenyl]sulfonyloxyphenyl]carbamoylamino]phenyl] acetate Chemical compound CC(=O)OC1=CC=CC(=C1)NC(=O)NC2=CC(=CC=C2)OS(=O)(=O)C3=CC(=CC=C3)S(=O)(=O)OC4=CC=CC(=C4)NC(=O)NC5=CC(=CC=C5)OC(=O)C XPNPQJYPKUUKRI-UHFFFAOYSA-N 0.000 description 3
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- LHBFNEPVFKBQPS-UHFFFAOYSA-N bis[3-[[3-(benzenesulfonyloxy)phenyl]carbamoylamino]phenyl] benzene-1,3-disulfonate Chemical compound C1=CC=C(C=C1)S(=O)(=O)OC2=CC=CC(=C2)NC(=O)NC3=CC(=CC=C3)OS(=O)(=O)C4=CC(=CC=C4)S(=O)(=O)OC5=CC=CC(=C5)NC(=O)NC6=CC(=CC=C6)OS(=O)(=O)C7=CC=CC=C7 LHBFNEPVFKBQPS-UHFFFAOYSA-N 0.000 description 3
- FMNYAIDPSBEWRU-UHFFFAOYSA-N bis[4-[[4-(4-methylphenyl)sulfonyloxyphenyl]carbamoylamino]phenyl] benzene-1,3-disulfonate Chemical compound CC1=CC=C(C=C1)S(=O)(=O)OC2=CC=C(C=C2)NC(=O)NC3=CC=C(C=C3)OS(=O)(=O)C4=CC(=CC=C4)S(=O)(=O)OC5=CC=C(C=C5)NC(=O)NC6=CC=C(C=C6)OS(=O)(=O)C7=CC=C(C=C7)C FMNYAIDPSBEWRU-UHFFFAOYSA-N 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 3
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- 125000001424 substituent group Chemical group 0.000 description 3
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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 3
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- OQOLSESLQNHUPJ-NSHDSACASA-N (2s)-2-[(3-methylphenyl)carbamoylamino]-4-methylsulfanylbutanoic acid Chemical compound CSCC[C@@H](C(O)=O)NC(=O)NC1=CC=CC(C)=C1 OQOLSESLQNHUPJ-NSHDSACASA-N 0.000 description 2
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- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
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- 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 2
- UIFAEJQCFLEWCF-UHFFFAOYSA-N 1-methyl-4-[2-(4-methylphenoxy)ethoxy]benzene Chemical compound C1=CC(C)=CC=C1OCCOC1=CC=C(C)C=C1 UIFAEJQCFLEWCF-UHFFFAOYSA-N 0.000 description 2
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 2
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- DMZZUWOTJSCADW-UHFFFAOYSA-N bis[3-[(3-naphthalen-2-ylsulfonyloxyphenyl)carbamoylamino]phenyl] benzene-1,3-dicarboxylate Chemical compound C1=CC=C2C=C(C=CC2=C1)S(=O)(=O)OC3=CC=CC(=C3)NC(=O)NC4=CC(=CC=C4)OC(=O)C5=CC(=CC=C5)C(=O)OC6=CC=CC(=C6)NC(=O)NC7=CC(=CC=C7)OS(=O)(=O)C8=CC9=CC=CC=C9C=C8 DMZZUWOTJSCADW-UHFFFAOYSA-N 0.000 description 1
- JYFIFJNQCFZRDH-UHFFFAOYSA-N bis[3-[(3-naphthalen-2-ylsulfonyloxyphenyl)carbamoylamino]phenyl] benzene-1,3-disulfonate Chemical compound C1=CC=C2C=C(C=CC2=C1)S(=O)(=O)OC3=CC=CC(=C3)NC(=O)NC4=CC(=CC=C4)OS(=O)(=O)C5=CC(=CC=C5)S(=O)(=O)OC6=CC=CC(=C6)NC(=O)NC7=CC(=CC=C7)OS(=O)(=O)C8=CC9=CC=CC=C9C=C8 JYFIFJNQCFZRDH-UHFFFAOYSA-N 0.000 description 1
- SMPZPZIKYXMHPY-UHFFFAOYSA-N bis[3-[(3-naphthalen-2-ylsulfonyloxyphenyl)carbamoylamino]phenyl] benzene-1,4-dicarboxylate Chemical compound C1=CC=C2C=C(C=CC2=C1)S(=O)(=O)OC3=CC=CC(=C3)NC(=O)NC4=CC(=CC=C4)OC(=O)C5=CC=C(C=C5)C(=O)OC6=CC=CC(=C6)NC(=O)NC7=CC(=CC=C7)OS(=O)(=O)C8=CC9=CC=CC=C9C=C8 SMPZPZIKYXMHPY-UHFFFAOYSA-N 0.000 description 1
- QFWJBBBNFCZCRK-UHFFFAOYSA-N bis[3-[(3-phenoxyphenyl)carbamoylamino]phenyl] benzene-1,3-disulfonate Chemical compound C1=CC=C(C=C1)OC2=CC=CC(=C2)NC(=O)NC3=CC(=CC=C3)OS(=O)(=O)C4=CC(=CC=C4)S(=O)(=O)OC5=CC=CC(=C5)NC(=O)NC6=CC(=CC=C6)OC7=CC=CC=C7 QFWJBBBNFCZCRK-UHFFFAOYSA-N 0.000 description 1
- NRZJVPKAIMLBKT-UHFFFAOYSA-N bis[3-[(3-phenylmethoxyphenyl)carbamoylamino]phenyl] benzene-1,3-disulfonate Chemical compound C1=CC=C(C=C1)COC2=CC=CC(=C2)NC(=O)NC3=CC(=CC=C3)OS(=O)(=O)C4=CC(=CC=C4)S(=O)(=O)OC5=CC=CC(=C5)NC(=O)NC6=CC(=CC=C6)OCC7=CC=CC=C7 NRZJVPKAIMLBKT-UHFFFAOYSA-N 0.000 description 1
- ODKYGDSUYWSJEY-UHFFFAOYSA-N bis[3-[(3-propylsulfonyloxyphenyl)carbamoylamino]phenyl] benzene-1,3-disulfonate Chemical compound CCCS(=O)(=O)OC1=CC=CC(=C1)NC(=O)NC2=CC(=CC=C2)OS(=O)(=O)C3=CC(=CC=C3)S(=O)(=O)OC4=CC=CC(=C4)NC(=O)NC5=CC(=CC=C5)OS(=O)(=O)CCC ODKYGDSUYWSJEY-UHFFFAOYSA-N 0.000 description 1
- RELVKZWEZVSFBO-UHFFFAOYSA-N bis[3-[[3-(3-methylphenyl)sulfonyloxyphenyl]carbamoylamino]phenyl] benzene-1,3-disulfonate Chemical compound CC1=CC(=CC=C1)S(=O)(=O)OC2=CC=CC(=C2)NC(=O)NC3=CC(=CC=C3)OS(=O)(=O)C4=CC(=CC=C4)S(=O)(=O)OC5=CC=CC(=C5)NC(=O)NC6=CC(=CC=C6)OS(=O)(=O)C7=CC=CC(=C7)C RELVKZWEZVSFBO-UHFFFAOYSA-N 0.000 description 1
- OGMZWFULXQRFLF-UHFFFAOYSA-N bis[3-[[3-(4-chlorophenyl)sulfonyloxyphenyl]carbamoylamino]phenyl] benzene-1,3-disulfonate Chemical compound C1=CC(=CC(=C1)OS(=O)(=O)C2=CC=C(C=C2)Cl)NC(=O)NC3=CC(=CC=C3)OS(=O)(=O)C4=CC(=CC=C4)S(=O)(=O)OC5=CC=CC(=C5)NC(=O)NC6=CC(=CC=C6)OS(=O)(=O)C7=CC=C(C=C7)Cl OGMZWFULXQRFLF-UHFFFAOYSA-N 0.000 description 1
- BQNQUTSLOIETDK-UHFFFAOYSA-N bis[3-[[3-(4-methoxyphenyl)sulfonyloxyphenyl]carbamoylamino]phenyl] benzene-1,3-disulfonate Chemical compound COC1=CC=C(C=C1)S(=O)(=O)OC2=CC=CC(=C2)NC(=O)NC3=CC(=CC=C3)OS(=O)(=O)C4=CC(=CC=C4)S(=O)(=O)OC5=CC=CC(=C5)NC(=O)NC6=CC(=CC=C6)OS(=O)(=O)C7=CC=C(C=C7)OC BQNQUTSLOIETDK-UHFFFAOYSA-N 0.000 description 1
- AFWYGUDOOHLCBO-UHFFFAOYSA-N bis[3-[[3-(4-methylphenyl)sulfonyloxyphenyl]carbamoylamino]phenyl] benzene-1,2-disulfonate Chemical compound CC1=CC=C(C=C1)S(=O)(=O)OC2=CC=CC(=C2)NC(=O)NC3=CC(=CC=C3)OS(=O)(=O)C4=CC=CC=C4S(=O)(=O)OC5=CC=CC(=C5)NC(=O)NC6=CC(=CC=C6)OS(=O)(=O)C7=CC=C(C=C7)C AFWYGUDOOHLCBO-UHFFFAOYSA-N 0.000 description 1
- QYJDKKLLNVYCSS-UHFFFAOYSA-N bis[3-[[3-(butylcarbamoyloxy)phenyl]carbamoylamino]phenyl] benzene-1,3-disulfonate Chemical compound CCCCNC(=O)OC1=CC=CC(=C1)NC(=O)NC2=CC(=CC=C2)OS(=O)(=O)C3=CC(=CC=C3)S(=O)(=O)OC4=CC=CC(=C4)NC(=O)NC5=CC(=CC=C5)OC(=O)NCCCC QYJDKKLLNVYCSS-UHFFFAOYSA-N 0.000 description 1
- HMCNLBXHEQFCQB-UHFFFAOYSA-N bis[3-[[3-(hexylcarbamoyloxy)phenyl]carbamoylamino]phenyl] benzene-1,3-disulfonate Chemical compound CCCCCCNC(=O)OC1=CC=CC(=C1)NC(=O)NC2=CC(=CC=C2)OS(=O)(=O)C3=CC(=CC=C3)S(=O)(=O)OC4=CC=CC(=C4)NC(=O)NC5=CC(=CC=C5)OC(=O)NCCCCCC HMCNLBXHEQFCQB-UHFFFAOYSA-N 0.000 description 1
- KQXJTFIMPMVKTA-UHFFFAOYSA-N bis[3-[[3-(naphthalen-2-ylcarbamoyloxy)phenyl]carbamoylamino]phenyl] benzene-1,3-disulfonate Chemical compound C1=CC=C2C=C(C=CC2=C1)NC(=O)OC3=CC=CC(=C3)NC(=O)NC4=CC(=CC=C4)OS(=O)(=O)C5=CC(=CC=C5)S(=O)(=O)OC6=CC=CC(=C6)NC(=O)NC7=CC(=CC=C7)OC(=O)NC8=CC9=CC=CC=C9C=C8 KQXJTFIMPMVKTA-UHFFFAOYSA-N 0.000 description 1
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- NZZGQZMNFCTNAM-UHFFFAOYSA-N naphthalene-2,6-dicarbonyl chloride Chemical compound C1=C(C(Cl)=O)C=CC2=CC(C(=O)Cl)=CC=C21 NZZGQZMNFCTNAM-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- XNLBCXGRQWUJLU-UHFFFAOYSA-N naphthalene-2-carbonyl chloride Chemical compound C1=CC=CC2=CC(C(=O)Cl)=CC=C21 XNLBCXGRQWUJLU-UHFFFAOYSA-N 0.000 description 1
- OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- 235000013873 oxidized polyethylene wax Nutrition 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- KPBSJEBFALFJTO-UHFFFAOYSA-N propane-1-sulfonyl chloride Chemical compound CCCS(Cl)(=O)=O KPBSJEBFALFJTO-UHFFFAOYSA-N 0.000 description 1
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 125000006410 propenylene group Chemical group 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical class CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 239000013053 water resistant agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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- Heat Sensitive Colour Forming Recording (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
更に近年は4,4’−イソプロピリデンジフェノールや4,4’−ビスフェノールスルホンなどは、環境ホルモンや変異原性などの環境衛生上の問題が指摘されているため、これらの問題のない非フェノール系顕色剤が求められているのが実情である。
[1]下記一般式(1)で表されるN,N’−ジアリール尿素誘導体。
R1は、アルキル基、アルケニル基、アルキルオキシアルキル基、アラルキル基、アリール基、アルキルスルホニル基、アラルキルスルホニル基、アリールスルホニル基、アシル基、アルキルアミノカルボニル基、又は、アリールアミノカルボニル基である。
−O−Z−O−、R1−O−の少なくとも一方はスルホン酸エステルを含む。A、Bは水素原子若しくはメチル基である。a,bは1〜4の整数である。
nは1〜7の整数である。)
R2はC1〜C4のアルキル基、C1〜C3のアルコキシ基、又は、ハロゲン原子である。
cは1〜4の整数であり、nは1〜7の整数である。)
R1は、アルキル基、アルケニル基、アルキルオキシアルキル基、アラルキル基、アリール基、アルキルスルホニル基、アラルキルスルホニル基、アリールスルホニル基、アシル基、アルキルアミノカルボニル基、又は、アリールアミノカルボニル基である。
−O−Z−O−、R1−O−の少なくとも一方はスルホン酸エステルを含む。A、Bは水素原子若しくはメチル基である。a,bは1〜4の整数である。)
A、Bは水素原子若しくはメチル基である。a,bは1〜4の整数である。
nは1〜7の整数である。)
Xはハロゲン、アシルオキシ基、又は、イソシアネート基である。)
A、Bは水素原子若しくはメチル基である。a,bは1〜4の整数である。
nは1〜7の整数である。)
A、Bは水素原子若しくはメチル基である。a,bは1〜4の整数である。)
Xはハロゲン、アシルオキシ基、又は、イソシアネート基である。)
本発明のN,N’−ジアリール尿素誘導体は、前記一般式(1)で表される。また、本発明のN,N’−ジアリール尿素誘導体は、前記一般式(2)〜(8)で表されるものであってもよい。
好ましい2価の基としては、フェニレン基、ジフェニルジイル基、オキシビス(フェニレン)基(-Ph-O-Ph-基)、C2〜C6のアルキレン基、−C2H4OC2H4−基である。
1,3−ビス(3−{3−[3−(メタンスルホニルオキシ)フェニル]ウレイド}フェニルオキシカルボニル)ベンゼン、1,3−ビス(3−{3−[3−(ベンゼンスルホニルオキシ)フェニル]ウレイド}フェニルオキシカルボニル)ベンゼン、1,3−ビス(3−{3−[3−(2−ナフタレンスルホニルオキシ)フェニル]ウレイド}フェニルオキシカルボニル)ベンゼン
本発明のN,N’−ジアリール尿素誘導体は、合成中間体として有用な前記一般式(9)で表される化合物と前記一般式(10)で表される化合物を塩基存在下に反応させることによって合成することができる。前記一般式(9)で表される化合物は、一般式(11)で表される化合物と一般式(12)で表される芳香族アミン化合物を塩基存在下に反応させることによって合成することもできる。
(合成方法1)
式(5)(n=1〜7)の合成原料として有用な式(9)の化合物は、塩基存在下にN,N’-ビス(3-ヒドロキシフェニル)尿素と式(12)で表される2価の基を有する化合物を反応させることによって合成される。
式(5)(n=1〜7)の化合物は、式(9)の化合物と式(10)の化合物を塩基存在下に反応させることによって得ることができる。
反応方法2.式(5)(n=1)の化合物:
式(11)の化合物と式(12)の化合物を塩基存在下に反応させることによって得られる。式(11)の3-ヒドロキシ-3’-置換オキシ-ジフェニル尿素は、3,3’-ジフェニル尿素と式(10)で表される1価の反応性置換基(すなわち、ハロゲン、アシルオキシ基などの脱離基、又は、イソシアネート基)を有する化合物を塩基存在下に反応させて得ることができる。
無水酢酸、無水プロピオン酸、無水安息香酸などの酸無水物;
本発明の感熱記録材料は、常温で無色ないし淡色の塩基性染料と、加熱により該塩基性染料と接触して呈色し得る顕色剤とを含有する感熱記録層を支持体上に設けた感熱記録材料であって、前記顕色剤が、前記のN,N’−ジアリール尿素誘導体である。
下塗り層の組成は、目的のより適宜選択すればよいが、一般に、バインダー、顔料などが含まれる。
更に、感度の向上を図るため、発泡系樹脂を使用することもできる。
下塗り層は1層でも良く、場合によっては2層以上設けてもよい。
保護層に用いられるバインダー、顔料、助剤は、上記の感熱記録層で用いられるものを使用される。
光沢層としては、例えば電子線または紫外線硬化性化合物を主成分とする塗液を塗布後、電子線や紫外線を照射して硬化させる方法や超微粒子のコアシェル型アクリル樹脂を使用する方法等が挙げられる。
または更に、支持体の裏面側に帯電防止層を設けてもよい。
HPLC分析は島津製作所社製HPLC分析装置を用い、測定は溶離液:CH3CN/0.05%リン酸水=80/20(vol/vol%)、流速:0.8ml/min、カラム温度:40℃、検出波長:254nmの条件でおこなった。
1,3−ビス(3−{3−[3−(p−トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼンの合成
温度計、攪拌機を付した四ツ口フラスコにN-3-ヒドロキシフェニル-N'-3' -(p-トルエンスルホニルオキシ)フェニル尿素7.96g、酢酸エチル80g、トリエチルアミン2.5gを仕込み60℃に加温した後、酢酸エチルに溶解したベンゼン−1,3−ジスルホニルクロライド2.89gを滴下し4時間反応した。反応終了後、有機層を希薄NaOH水溶液、塩酸水溶液で水洗し、中和・水洗した。溶媒を留去した後、メタノールで結晶化した。
式(5):n=1〜7の化合物合成
式(5):n=1〜7の化合物合成
上記で得られた固形物を少量の酢酸エチル/THF溶媒に溶解し、その溶解液のシリカゲルクロマトグラフィーをおこなった。トルエン/酢酸エチル/酢酸=10/1/0.05(容量比)の溶離液を用いて、組成物の各成分を溶出単離した。各成分の溶出液をそれぞれ濃縮してn=1成分、n=2成分(図4にIRチャートを示す。図5に1H−NMRスペクトルを示す。図6にFDマススペクトルを示す。)、n=3成分(図7にIRチャートを示す。)、n=4成分(図8にIRチャートを示す。)、n=5成分(図9にIRチャートを示す。)、n=6成分(図10にIRチャートを示す。)の機器分析を行った。n=2成分は、式(5)のn=2成分であることを確認した。
1,3−ビス(3−{3−[3−(ベンゼンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼンの合成
合成例1のN−3−ヒドロキシフェニル−N’−3’−(p−トルエンスルホニルオキシ)フェニル尿素7.96gをN-3-ヒドロキシフェニル-N'-3'-(ベンゼンスルホニルオキシ)フェニル尿素7.68gに代える以外合成例1と同様の操作をして1,3-ビス(3-{3-[3-(ベンゼンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼンを合成した。図11にIRチャートを示す。
1,3−ビス(3−{3−[3−(メシチレンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼンの合成
合成例1のN-3-ヒドロキシフェニル-N'-3'-(p-トルエンスルホニルオキシ)フェニル尿素7.96をN-3-ヒドロキシフェニル-N'-3'-(メシチレンスルホニルオキシ)フェニル尿素8.58gに代える以外合成例1と同様の操作をして1,3-ビス(3-{3-[3-(メシチレンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼンを合成した。図12にIRチャートを示す。
4,4' -ビス(3-{3-[3-(p-トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ビフェニルの合成
合成例1のN-3-ヒドロキシフェニル-N'-3'-(p-トルエンスルホニルオキシ)フェニル尿素7.96gをN-3-ヒドロキシフェニル-N'-3'-(ベンゼンスルホニルオキシ)フェニル尿素7.96gに代え、ベンゼン-1,3-ジスルホニルクロライド2.89gをビフェニル-4,4’-スルホニルクロライド3.86gに代える以外合成例1と同様の操作をして4,4' -ビス(3-{3-[3-(p-トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ビフェニルを合成した。図13にIRチャートを示す。
1,3-ビス(4-{3-[4-(p-トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼンの合成
合成例1のN-3-ヒドロキシフェニル-N'-3'-(p-トルエンスルホニルオキシ)フェニル尿素7.96gをN-4-ヒドロキシフェニル-N'-4'-(p-トルエンスルホニルオキシ)フェニル尿素7.96gに代える以外合成例1と同様の操作をして1,3-ビス(4-{3-[4-(p-トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼンを合成した。図14にIRチャートを示す。
1,3-ビス(3-{3-[3-(p-トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシカルボニル)ベンゼンの合成
合成例1のベンゼン-1,3-ジスルホニルクロライド2.89gをイソフタル酸ジクロライド2.24gに代える以外合成例1と同様の操作をして、1,3-ビス(3-{3-[3-(p-トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシカルボニル)ベンゼンを合成した。図15にIRチャートを示す。
1,3-ビス(3-{3-[3-(メタンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼンの合成
合成例1のN-3-ヒドロキシフェニル-N'-3'-(p-トルエンスルホニルオキシ)フェニル尿素7.96gをN-3-ヒドロキシフェニル-N'-3'-(メタンスルホニルオキシ)フェニル尿素6.44に代える以外合成例1と同様の操作をして1,3-ビス(3-{3-[3-(メタンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼンを合成した。
1−メチル−2,4−ビス(3−{3−[3−(p−トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシカルボニルアミノ)ベンゼンの合成
合成例1のベンゼン-1,3-ジスルホニルクロライド2.89gをトリレン-2,4-ジイソシアネート1.92gに代える以外合成例1と同様の操作をして、1−メチル−2,4−ビス(3−{3−[3−(p−トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシカルボニルアミノ)ベンゼンを合成した。
4,4’−ビス(3−[3−{3−(p−トルエンスルホニルオキシ)フェニル}ウレイド]フェニルオキシスルホニル)ジフェニルエーテルの合成
合成例1のベンゼン−1,3−ジスルホニルクロライド2.89gに代えて4,4−オキシビス(ベンゼンスルホニルクロライド)3.86gに代える以外、合成例1と同様の操作をして4,4’−ビス(3−[3−{3−(p−トルエンスルホニルオキシ)フェニル}ウレイド]フェニルオキシスルホニル)ジフェニルエーテルを合成した。図16にIRチャートを示す。
プラスチック中空粒子(商品名:ローペイクSN−1055:中空率:55%、固形分26.5%)100部、焼成カオリンの50%分散液100部、スチレン−ブタジエン系ラテックス(商品名:L−1571 固形分48%)25部、酸化澱粉の10%水溶液50部および水20部を混合して、アンダーコート用塗料を作成した。
[感熱記録用塗料の作成]
A液(染料分散液の調製)
3−(N,N−ジブチルアミノ)−6−メチル−7−アニリノフルオラン 10部
10%ポリビニルアルコール水溶液 10部
水 16.7部
1,3-ビス(3-{3-[3-(p-トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼン (合成例1) 20部
10%ポリビニルアルコール水溶液 20部
水 33.3部
1,2−ビス(m−トリルオキシ)エタン 15部
10%ポリビニルアルコール水溶液 15部
水 25部
A液(染料剤分散液) 36.7部
B液(顕色剤分散液) 73.3部
C液(増感剤分散液) 55.0部
支持体として坪量が53gの上質紙(酸性紙)にアンダーコート用塗料を乾燥後の面積当たりの質量が6g/m2となるように塗布および乾燥し、その後、感熱記録層用塗料を、乾燥後の面積当たりの質量が3.8g/m2になるように塗布乾燥した。
このシートをス−パーカレンダーで平滑度(JISP8155:2010)が900〜1200sになるように処理して感熱記録材料を作成した。
1.感熱記録性試験(発色試験)
作成した感熱記録材料について、感熱記録紙印字試験機(大倉電気社製TH−PMD)を用い、印加エネルギー0.38mJ/dotで印加した。記録部の印字濃度はマクベス反射濃度計RD−914で測定した。これを試験前サンプル(ブランク)とした。
感熱記録性試験で印加エネルギー0.38mJ/dotで記録した感熱記録材料を試験温度40℃、90%RHの環境下に24時間放置した後、試験片の印字部画像濃度と未印字部の濃度をマクベス反射濃度計で測定した。
感熱記録性試験で印加エネルギー0.38mJ/dotで記録した感熱記録材料を試験温度60℃の恒温環境下に24時間放置した後、試験片の印字部画像濃度と未印字部の濃度をマクベス反射濃度計で測定した。
感熱記録性試験で印加エネルギー0.38mJ/dotで記録した感熱記録材料を5000Luxに100時間暴露しその後、画像濃度をマクベス反射濃度計で測定した。
感熱記録性試験で印加エネルギー0.38mJ/dotで記録した感熱記録材料を水中に15時間浸漬しその後、試験片を風乾させ、画像濃度と未印字部をマクベス反射濃度計で測定した。
感熱記録性試験で印加エネルギー0.38mJ/dotで記録した感熱記録材料にサラダオイル中に10分間浸漬しその後、試験片の油をふき取り、画像濃度をマクベス反射濃度計で測定した。
感熱記録性試験で印加エネルギー0.38mJ/dotで記録した感熱記録材料にサラダオイル中に3時間浸漬しその後、試験片の油をふき取り、画像濃度をマクベス反射濃度計で測定した。この実施例による感熱記録材料の各種試験結果は、表3に記載の通りであった。
実施例1のB液の1,3-ビス(3-{3-[3-(p-トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼン(合成例1)を合成例2の固形物に代える以外は実施例1と同様の操作をおこなった。
この実施例による感熱記録材料の各種試験結果は、表3に記載の通りであった。
実施例1のB液の1,3-ビス(3-{3-[3-(p-トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼン (合成例1)を合成例3のn=2の化合物に代える以外は実施例1と同様の操作をおこなった。
この実施例による感熱記録材料の各種試験結果は、表3に記載の通りであった。
実施例1のB液の1,3-ビス(3-{3-[3-(p-トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼンを 合成例4に代える以外は実施例1と同様の操作をおこなった。
この実施例による感熱記録材料の各種試験結果は、表3に記載の通りであった。
実施例1のB液の1,3-ビス(3-{3-[3-(p-トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼン (合成例1)を合成例5に代える以外は実施例1と同様の操作をおこなった。
この実施例による感熱記録材料の各種試験結果は、表3に記載の通りであった。
実施例1のB液の1,3-ビス(3-{3-[3-(p-トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼン (合成例1)を合成例6に代える以外は実施例1と同様の操作をおこなった。
この実施例による感熱記録材料の各種試験結果は、表3に記載の通りであった。
実施例1のB液の1,3-ビス(3-{3-[3-(p-トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼン (合成例1)を合成例7に代える以外は実施例1と同様の操作をおこなった。
この実施例による感熱記録材料の各種試験結果は、表3に記載の通りであった。
実施例1のB液の1,3-ビス(3-{3-[3-(p-トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼン (合成例1)を合成例8に代える以外は実施例1と同様の操作をおこなった。
この実施例による感熱記録材料の各種試験結果は、表3に記載の通りであった。
実施例1のB液の1,3-ビス(3-{3-[3-(p-トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼン (合成例1)を4,4’−イソプロピリデンジフェノール(ビスフェノールA)に代える以外は実施例1と同様の操作をおこなった。この参照例による感熱記録材料の各種試験結果は、表3に記載の通りであった。
実施例1のB液の1,3-ビス(3-{3-[3-(p-トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼン (合成例1)を4,4’−ジヒドロキシジフェニルスルホン(ビスフェノールS)に代える以外は実施例1と同様の操作をおこなった。この参照例による感熱記録材料の各種試験結果は、表3に記載の通りであった。
実施例1のB液の1,3-ビス(3-{3-[3-(p-トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼン (合成例1)を4−アリルオキシ−4’−ヒドロキシジフェニルスルホンに代える以外は実施例1と同様の操作をおこなった。この参照例による感熱記録材料の各種試験結果は、表3に記載の通りであった。
実施例1のB液の1,3-ビス(3-{3-[3-(p-トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼン (合成例1)を4−ヒドロキシ−4’−イソプロピルオキシ−ジフェニルスルホンに代える以外は実施例1と同様の操作をおこなった。この参照例による感熱記録材料の各種試験結果は、表3に記載の通りであった。
実施例1のB液の1,3-ビス(3-{3-[3-(p-トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼン (合成例1)をN−3−(p−トルエンスルホニルオキシ)フェニル−N’−(p−トルエンスルホニル)−尿素に代える以外は実施例1と同様の操作をおこなった。この参照例による感熱記録材料の各種試験結果は、表3に記載の通りであった。
実施例1のB液の1,3-ビス(3-{3-[3-(p-トルエンスルホニルオキシ)フェニル]ウレイド}フェニルオキシスルホニル)ベンゼン (合成例1)をN−(2−(3−フェニルウレイド)フェニル)−ベンゼンスルホンアミドに代える以外は実施例1と同様の操作をおこなった。この参照例による感熱記録材料の各種試験結果は、表3に記載の通りであった。
Claims (9)
- 下記一般式(1)で表されるN,N’−ジアリール尿素誘導体。
R1は、アルキル基、アルケニル基、アルキルオキシアルキル基、アラルキル基、アリール基、アルキルスルホニル基、アラルキルスルホニル基、アリールスルホニル基、アシル基、アルキルアミノカルボニル基、又は、アリールアミノカルボニル基である。
−O−Z−O−、R1−O−の少なくとも一方はスルホン酸エステルを含む。A、Bは水素原子若しくはメチル基である。a,bは1〜4の整数である。
nは1〜7の整数である。) - 下記一般式(2)で表される、請求項1に記載のN,N’−ジアリール尿素誘導体。
R2はC1〜C4のアルキル基、C1〜C3のアルコキシ基、又は、ハロゲン原子である。
cは1〜4の整数であり、nは1〜7の整数である。) - 下記一般式(3)で表される、請求項1に記載のN,N’−ジアリール尿素誘導体。
R1は、アルキル基、アルケニル基、アルキルオキシアルキル基、アラルキル基、アリール基、アルキルスルホニル基、アラルキルスルホニル基、アリールスルホニル基、アシル基、アルキルアミノカルボニル基、又は、アリールアミノカルボニル基である。
−O−Z−O−、R1−O−の少なくとも一方はスルホン酸エステルを含む。A、Bは水素原子若しくはメチル基である。a,bは1〜4の整数である。) - 下記一般式(9)で表される化合物と、下記一般式(10)で表される化合物とを、塩基存在下に反応させる、請求項1〜5のいずれか一項に記載のN,N’−ジアリール尿素誘導体の製造方法。
A、Bは水素原子若しくはメチル基である。a,bは1〜4の整数である。
nは1〜7の整数である。)
Xはハロゲン、アシルオキシ基、又は、イソシアネート基である。) - 下記一般式(9)で表されるジアリール尿素誘導体。
A、Bは水素原子若しくはメチル基である。a,bは1〜4の整数である。
nは1〜7の整数である。) - 下記一般式(11)で表される化合物と、下記一般式(12)で表される化合物とを、塩基存在下に反応させる、請求項1〜5のいずれか一項に記載のN,N’−ジアリール尿素誘導体の製造方法。
A、Bは水素原子若しくはメチル基である。a,bは1〜4の整数である。)
Xはハロゲン、アシルオキシ基、又は、イソシアネート基である。) - 常温で無色ないし淡色の塩基性染料と、加熱により該染料と接触して呈色し得る顕色剤とを含有する感熱記録層を支持体上に設けた感熱記録材料であって、前記顕色剤が、請求項1〜5のいずれか一項に記載のN,N’−ジアリール尿素誘導体を含有することを特徴とする感熱記録材料。
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