JPH0447988A - Thermal recording material - Google Patents
Thermal recording materialInfo
- Publication number
- JPH0447988A JPH0447988A JP2156682A JP15668290A JPH0447988A JP H0447988 A JPH0447988 A JP H0447988A JP 2156682 A JP2156682 A JP 2156682A JP 15668290 A JP15668290 A JP 15668290A JP H0447988 A JPH0447988 A JP H0447988A
- Authority
- JP
- Japan
- Prior art keywords
- group
- ethyl
- electron
- compound
- methyl
- 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.)
- Pending
Links
- 239000000463 material Substances 0.000 title claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 150000001408 amides Chemical class 0.000 claims abstract description 4
- 239000004202 carbamide Substances 0.000 claims abstract description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 238000004040 coloring Methods 0.000 abstract description 8
- 229910052751 metal Inorganic materials 0.000 abstract description 7
- 239000002184 metal Substances 0.000 abstract description 7
- 239000002904 solvent Substances 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 4
- 150000002989 phenols Chemical class 0.000 abstract description 4
- 150000003839 salts Chemical class 0.000 abstract description 4
- 229920003986 novolac Polymers 0.000 abstract description 3
- 239000000440 bentonite Substances 0.000 abstract description 2
- 229910000278 bentonite Inorganic materials 0.000 abstract description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004927 clay Substances 0.000 abstract description 2
- WLNBMPZUVDTASE-HXIISURNSA-N (2r,3r,4s,5r)-2-amino-3,4,5,6-tetrahydroxyhexanal;sulfuric acid Chemical compound [O-]S([O-])(=O)=O.O=C[C@H]([NH3+])[C@@H](O)[C@H](O)[C@H](O)CO.O=C[C@H]([NH3+])[C@@H](O)[C@H](O)[C@H](O)CO WLNBMPZUVDTASE-HXIISURNSA-N 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- -1 furkyl group Chemical group 0.000 description 21
- 125000001424 substituent group Chemical group 0.000 description 13
- 239000000975 dye Substances 0.000 description 12
- 239000010410 layer Substances 0.000 description 11
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 description 5
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 239000011241 protective layer Substances 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- RIFJZWMZWXKUSM-UHFFFAOYSA-N 19-aminononadecan-1-ol Chemical compound NCCCCCCCCCCCCCCCCCCCO RIFJZWMZWXKUSM-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 230000000052 comparative effect Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 125000004953 trihalomethyl group Chemical group 0.000 description 3
- 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
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000007864 aqueous solution 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- GJNDMSSZEBNLPU-UHFFFAOYSA-N octadecylurea Chemical compound CCCCCCCCCCCCCCCCCCNC(N)=O GJNDMSSZEBNLPU-UHFFFAOYSA-N 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 150000004961 triphenylmethanes Chemical class 0.000 description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- IOGPZWCEELGKFR-UHFFFAOYSA-N 1-(2,3-dimethylphenyl)sulfonyl-2,3-dimethylbenzene Chemical compound CC1=CC=CC(S(=O)(=O)C=2C(=C(C)C=CC=2)C)=C1C IOGPZWCEELGKFR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SOEIMWZLWIMMBM-UHFFFAOYSA-N 2-chloro-4-[1-(3-chloro-4-hydroxyphenyl)-2-ethylbutyl]phenol Chemical compound C=1C=C(O)C(Cl)=CC=1C(C(CC)CC)C1=CC=C(O)C(Cl)=C1 SOEIMWZLWIMMBM-UHFFFAOYSA-N 0.000 description 1
- XDZMPRGFOOFSBL-UHFFFAOYSA-N 2-ethoxybenzoic acid Chemical compound CCOC1=CC=CC=C1C(O)=O XDZMPRGFOOFSBL-UHFFFAOYSA-N 0.000 description 1
- SKFOLYBAPCHLNS-UHFFFAOYSA-N 2-hexylperoxybenzoic acid Chemical compound CCCCCCOOC1=CC=CC=C1C(O)=O SKFOLYBAPCHLNS-UHFFFAOYSA-N 0.000 description 1
- UXDLAKCKZCACAX-UHFFFAOYSA-N 2-hydroxy-3,5-bis(1-phenylethyl)benzoic acid Chemical compound C=1C(C(C)C=2C=CC=CC=2)=C(O)C(C(O)=O)=CC=1C(C)C1=CC=CC=C1 UXDLAKCKZCACAX-UHFFFAOYSA-N 0.000 description 1
- RIMIAFGFELSXIR-UHFFFAOYSA-N 2-hydroxy-4-octadecoxybenzoic acid Chemical compound CCCCCCCCCCCCCCCCCCOC1=CC=C(C(O)=O)C(O)=C1 RIMIAFGFELSXIR-UHFFFAOYSA-N 0.000 description 1
- QTFBYOXLXAGBKB-UHFFFAOYSA-N 2-hydroxy-4-pentadecoxybenzoic acid Chemical compound CCCCCCCCCCCCCCCOC1=CC=C(C(O)=O)C(O)=C1 QTFBYOXLXAGBKB-UHFFFAOYSA-N 0.000 description 1
- ZCPCQTFJJJQCGQ-UHFFFAOYSA-N 2-hydroxy-4-pentadecylbenzoic acid Chemical compound CCCCCCCCCCCCCCCC1=CC=C(C(O)=O)C(O)=C1 ZCPCQTFJJJQCGQ-UHFFFAOYSA-N 0.000 description 1
- DYSSLYHWHAUXRB-UHFFFAOYSA-N 2-hydroxy-5-tetradecylbenzoic acid Chemical compound CCCCCCCCCCCCCCC1=CC=C(O)C(C(O)=O)=C1 DYSSLYHWHAUXRB-UHFFFAOYSA-N 0.000 description 1
- WLTCCDHHWYAMCG-UHFFFAOYSA-N 2-phenylmethoxynaphthalene Chemical compound C=1C=C2C=CC=CC2=CC=1OCC1=CC=CC=C1 WLTCCDHHWYAMCG-UHFFFAOYSA-N 0.000 description 1
- UYMBCDOGDVGEFA-UHFFFAOYSA-N 3-(1h-indol-2-yl)-3h-2-benzofuran-1-one Chemical class C12=CC=CC=C2C(=O)OC1C1=CC2=CC=CC=C2N1 UYMBCDOGDVGEFA-UHFFFAOYSA-N 0.000 description 1
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- DDZACMDGXVXOOH-UHFFFAOYSA-N 4-(4-methylphenyl)phenol Chemical compound C1=CC(C)=CC=C1C1=CC=C(O)C=C1 DDZACMDGXVXOOH-UHFFFAOYSA-N 0.000 description 1
- QBZPUSKHVURBGP-UHFFFAOYSA-N 4-[2-[2-(4-hydroxyphenyl)sulfanylethoxymethoxy]ethylsulfanyl]phenol Chemical compound C1=CC(O)=CC=C1SCCOCOCCSC1=CC=C(O)C=C1 QBZPUSKHVURBGP-UHFFFAOYSA-N 0.000 description 1
- QPOOMDFMBUZOQS-UHFFFAOYSA-N 4-dodecoxy-2-hydroxybenzoic acid Chemical compound CCCCCCCCCCCCOC1=CC=C(C(O)=O)C(O)=C1 QPOOMDFMBUZOQS-UHFFFAOYSA-N 0.000 description 1
- BJHIPIOXPKTZQO-UHFFFAOYSA-N 4-hexoxy-2-hydroxybenzoic acid Chemical compound CCCCCCOC1=CC=C(C(O)=O)C(O)=C1 BJHIPIOXPKTZQO-UHFFFAOYSA-N 0.000 description 1
- UCPHBOBSDYLTRD-UHFFFAOYSA-N 6-hexylidenecyclohexa-2,4-dien-1-ol Chemical compound C(CCCCC)=C1C(C=CC=C1)O UCPHBOBSDYLTRD-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000594009 Phoxinus phoxinus Species 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 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
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- 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 1
- 235000021240 caseins Nutrition 0.000 description 1
- 125000006011 chloroethoxy group Chemical group 0.000 description 1
- 239000006258 conductive agent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 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 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- MDQRDWAGHRLBPA-UHFFFAOYSA-N fluoroamine Chemical compound FN MDQRDWAGHRLBPA-UHFFFAOYSA-N 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- HSEMFIZWXHQJAE-UHFFFAOYSA-N hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(N)=O HSEMFIZWXHQJAE-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 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 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- VENJCACPSJGPCM-UHFFFAOYSA-N n-phenylhexadecanamide Chemical compound CCCCCCCCCCCCCCCC(=O)NC1=CC=CC=C1 VENJCACPSJGPCM-UHFFFAOYSA-N 0.000 description 1
- ZOLJFBQEKSZVCB-UHFFFAOYSA-N n-phenyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC1=CC=CC=C1 ZOLJFBQEKSZVCB-UHFFFAOYSA-N 0.000 description 1
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000005506 phthalide group Chemical group 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 150000004654 triazenes Chemical class 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Landscapes
- Heat Sensitive Colour Forming Recording (AREA)
Abstract
Description
【発明の詳細な説明】
(発明の分野)
本発明は感熱記録材料に関するものであり、さらに詳細
には電子供与性無色染料と電子受容性化合物を含有する
発色層を支持体上に設けた感熱記録材料に関する。DETAILED DESCRIPTION OF THE INVENTION (Field of the Invention) The present invention relates to a heat-sensitive recording material, and more particularly to a heat-sensitive recording material in which a coloring layer containing an electron-donating colorless dye and an electron-accepting compound is provided on a support. Concerning recording materials.
(従来技術)
電子供与性無色染料と電子受容性化合物を使用した記録
材料は、感圧紙、感熱紙、感光感圧紙、通電感熱記録紙
、感熱転写紙等として既によく知られている。たとえば
英国特許第2.140,449号、米国特許第4,48
0,052号、同第4.436.920号、特公昭60
−23992号、特開昭57−179836号、同60
−123556号、同60−123557号などに詳し
い。特に、感熱記録材料は特公昭43−4160号、特
公昭45−14039号公報等に詳しい。(Prior Art) Recording materials using electron-donating colorless dyes and electron-accepting compounds are already well known as pressure-sensitive paper, thermal paper, light-sensitive pressure-sensitive paper, electrically conductive thermal recording paper, thermal transfer paper, and the like. For example, British Patent No. 2,140,449, U.S. Patent No. 4,48
No. 0,052, No. 4.436.920, Special Publication No. 1986
-23992, JP-A-57-179836, JP-A No. 60
-123556, 60-123557, etc. for details. In particular, heat-sensitive recording materials are detailed in Japanese Patent Publications No. 43-4160 and Japanese Patent Publication No. 45-14039.
これらの感熱記録システムはファクシミリ、プリンター
、ラベル等の多分野に応用され、ニーズが拡大している
。従来は、高速記録、低エネルギー印字、ヘッドマツチ
ング性等に対する要望が強かったが、最近では、用途拡
大とともに、高感度でありながら、地肌保存性の優れた
感熱記録材料に対する要望が強まってきている。特に事
務用品として良く用いられる溶剤ペン・ジアゾ複写材料
・のりなどの接着剤等溶剤を用いられている製品を用い
た場合の耐性、更には印字の保存状態に於ける耐性等で
あり、これらの要求を満たすために、従来、保護層によ
る検討、耐溶剤性のある顕色剤の使用など多くの提案が
なされている。しかしながら、これらの方法では高感度
を実現することはできていない。また6位にアリールオ
キシ基またはアリールチオ基で置換されたアルキルアミ
ノ基を有するフルオラン誘導体を用いれば耐溶剤性を付
与できることを本発明者等は見出したが、該発色剤を使
用しても、十分な感度を得るにはいたっていなかった。These thermal recording systems are being applied to a wide range of fields such as facsimiles, printers, and labels, and their needs are expanding. In the past, there was a strong demand for high-speed recording, low-energy printing, head matching properties, etc., but recently, with the expansion of applications, there has been a growing demand for heat-sensitive recording materials that are highly sensitive and have excellent background preservation. There is. In particular, it is the resistance when using products that use solvents, such as adhesives such as solvent pens, diazo copying materials, and glue, which are often used as office supplies, and furthermore, the resistance in the storage state of printing, etc. In order to meet these demands, many proposals have been made, including consideration of protective layers and use of solvent-resistant color developers. However, these methods have not been able to achieve high sensitivity. In addition, the present inventors have found that solvent resistance can be imparted by using a fluoran derivative having an alkylamino group substituted with an aryloxy group or an arylthio group at the 6-position. However, I was not able to obtain sufficient sensitivity.
(発明の目的)
本発明の目的は発色特性をはじめとする諸性能に十分な
性能を付与し、かつ耐溶剤性を有した感熱記録材料を提
供することにある。(Objective of the Invention) An object of the present invention is to provide a heat-sensitive recording material which has sufficient performance in various properties including coloring properties and has solvent resistance.
(発明の構成)
本発明の目的は、電子供与性無色染料と電子受容性化合
物及び熱可融性化合物を含有してなる感熱記録材料にお
いて、該電子供与性無色染料として6位にアリールオキ
シ基またはアリールチオ基で置換されたアルキル7ミノ
基を有するフルオラン誘導体を含有し、かつ熱可融性化
合物として芳香環及び/又はアミド及び/又はウレアを
含む炭化水崇化合物を少なくとも1種以上含有すること
を特徴とする感熱記録材料により達成された。(Structure of the Invention) An object of the present invention is to provide a heat-sensitive recording material containing an electron-donating colorless dye, an electron-accepting compound, and a thermofusible compound, with an aryloxy group at the 6-position as the electron-donating colorless dye. Or it contains a fluoran derivative having an alkyl 7-mino group substituted with an arylthio group, and contains at least one hydrocarbon compound containing an aromatic ring and/or an amide and/or urea as a thermofusible compound. This was achieved using a heat-sensitive recording material characterized by:
本発明に使用される電子供与性無色染料は6位にアリー
ルオキシ基またはアリールチオ基で置換されたアリルア
ミノ基を有するフルオラン誘導体であるが、なかでも下
記−形式(1〕で示されるものが好ましい。The electron-donating colorless dye used in the present invention is a fluoran derivative having an arylamino group substituted with an aryloxy group or an arylthio group at the 6-position, and among them, those represented by the following format (1) are preferred.
〔1〕
(式中、R1およびR3はアルキル基、アルケニル基、
アルキニル基、アリール基、水素原子を、R2は水素原
子、フルキル基、アルコキシ基、ハロゲン原子を、R4
は水素原子アルキル基、アルケニル基、アルキニル基、
7リール基、アルコキシ基、アリールオキシ基、フルキ
ルチオ基、ハロゲン原子、置換7ミノ基、シアノ基、ニ
トロ基、アシル基、トリハロメチル基、スルファモイル
基を、×は酸素原子または硫黄原子を、Arおよび環へ
はへテロ原子を含んでいてもよい芳香環を、nは1〜1
0の整数、mは1〜3の整数を表す。[1] (wherein R1 and R3 are an alkyl group, an alkenyl group,
Alkynyl group, aryl group, hydrogen atom, R2 is hydrogen atom, furkyl group, alkoxy group, halogen atom, R4
is a hydrogen atom alkyl group, alkenyl group, alkynyl group,
7-aryl group, alkoxy group, aryloxy group, furkylthio group, halogen atom, substituted 7-mino group, cyano group, nitro group, acyl group, trihalomethyl group, sulfamoyl group, × represents oxygen atom or sulfur atom, Ar and The ring is an aromatic ring that may contain a heteroatom, and n is 1 to 1.
An integer of 0 and m represent an integer of 1 to 3.
牛サンテン環または環へは同一または異種の置換基を複
数個有していても良く、その場合の置換基はアルコキシ
基、ハロゲン原子、ニトロ基を表す。The bovine santhene ring or rings may have a plurality of the same or different substituents, and in this case, the substituents represent an alkoxy group, a halogen atom, or a nitro group.
上記−形式〔1〕においてR1で表される基は更に、フ
ルキル基、アルケニル基、アルキニル基、アリール基、
アルコキシ基、アリールオキシ基、アルキルチオ基、ハ
ロゲン原子、置換アミノ基、シアノ基、ニトロ基、7シ
ル基、トリハロメチル基、スルファモイル基、ヘゲ0環
残基等で置換されていてもろい。これらの置換基は更に
置換基を有していてもよい。R1としては、
H−CHz l−C−R2,−I Y Z 。The group represented by R1 in the above-format [1] further includes a furkyl group, an alkenyl group, an alkynyl group, an aryl group,
It may be substituted with an alkoxy group, an aryloxy group, an alkylthio group, a halogen atom, a substituted amino group, a cyano group, a nitro group, a 7-syl group, a trihalomethyl group, a sulfamoyl group, a Hege O-ring residue, or the like. These substituents may further have a substituent. As R1, H-CHzl-C-R2, -IYZ.
−CIl R2,−)、−〇。 R2,OC,R2,−
、Y Z 。-CIl R2, -), -〇. R2,OC,R2,-
,YZ.
(nは2〜10の整数、mは1〜5の整数、Yおよび2
は水素原子、アルキル基、アルケニル基、アルキニル基
、アリール基、アルコキシ基、アリールオキシ基、アル
キルチオ基、ハロゲン原子、置換アミノ基、シアノ基、
ニトロ基、アシル基、トリハロメチル基、スルファモイ
ル基、ヘテロ残基を示す。)が好ましい。(n is an integer from 2 to 10, m is an integer from 1 to 5, Y and 2
is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group, a halogen atom, a substituted amino group, a cyano group,
Indicates a nitro group, acyl group, trihalomethyl group, sulfamoyl group, and hetero residue. ) is preferred.
Rとして特にはメチル基、エチル基、プロピル基、ブチ
ル基等が好ましい。Particularly preferred R is a methyl group, ethyl group, propyl group, butyl group, or the like.
上式中、R2で表される基はアルキル基、アルケニル基
、フルキニル基、アルコキシ基、ハロゲン原子が好まし
く、特にメチル基、エチル基、メトキシ基、メトキシメ
チル基、メチルチオ基、塩素原子が好ましい。In the above formula, the group represented by R2 is preferably an alkyl group, an alkenyl group, a furkynyl group, an alkoxy group, or a halogen atom, and particularly a methyl group, an ethyl group, a methoxy group, a methoxymethyl group, a methylthio group, or a chlorine atom.
上式中、R3で表される基は水素原子、炭素原子数1〜
8のフルキル基が好ましく、特に水素原子、エチル基が
好ましい。In the above formula, the group represented by R3 is a hydrogen atom, and has 1 to 1 carbon atoms.
8 is preferable, and a hydrogen atom and an ethyl group are particularly preferable.
R4は水素原子、アルキル基、7リール基、アルコキシ
基、アルケニル基が好ましく、更に、ハロゲン原子、ア
ルコキシ基などの置換基を有していても良い。R4 is preferably a hydrogen atom, an alkyl group, a heptadyl group, an alkoxy group, or an alkenyl group, and may further have a substituent such as a halogen atom or an alkoxy group.
R4はベンゼン環上に1〜3個置換可能であり、複数個
の場合、同一であっても異なっていても良い。1 to 3 R4s can be substituted on the benzene ring, and in the case of multiple R4s, they may be the same or different.
R3が水素原子の場合、R4は水素原子または炭素原子
1〜8のアルキル基が好ましくい。R1がエチル基の場
合、R4はトリフルオロメチル基、ニトロ基、シアノ基
、スルファモイル基などが好ましい。When R3 is a hydrogen atom, R4 is preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. When R1 is an ethyl group, R4 is preferably a trifluoromethyl group, a nitro group, a cyano group, a sulfamoyl group, or the like.
上式中、環へはベンゼン環、ナフタレン環、ピリジン環
、ビリミダジン環、インドール環などが好ましく、特に
ベンゼン環が好ましい。In the above formula, the ring is preferably a benzene ring, a naphthalene ring, a pyridine ring, a birimidazine ring, an indole ring, etc., and a benzene ring is particularly preferred.
環Aが同一または異種の置換基で置換されている場合は
、置換基としては、ハロゲン原子、ニトロ基、シアノ基
、アルコキシ基などが好ましく、特に塩素原子、フッ素
原子が好ましい。When ring A is substituted with the same or different substituents, the substituent is preferably a halogen atom, a nitro group, a cyano group, an alkoxy group, etc., and a chlorine atom or a fluorine atom is particularly preferable.
上式中Arで表される芳香環は、ベンゼン環、ナフタレ
ン環、ピリジン環、フラン環、クマリン環などが好まし
く、特にベンゼン環、ナフタレン環が好ましい。The aromatic ring represented by Ar in the above formula is preferably a benzene ring, a naphthalene ring, a pyridine ring, a furan ring, a coumarin ring, etc., and a benzene ring or a naphthalene ring is particularly preferred.
Arの置換基としては、飽和又は不飽和のフルキル基、
ジクロフルキル基、7リール基、ヒドロキシ基、アルコ
キシ基、フルキスチオ基、7り−ルオキシ基、アリール
チオ基、ハロゲン原子、ジアルキル7ミ八Lカルボニル
基、カルボオキシ基、カルボキシル基、カルバモイル基
、フルコキシ力ルボニル基、7シル基、シアノ基、ニト
ロ基、スルホニル基、イソシアナート基、複素環残基な
どが好ましい。これらの置換基は更に、同様な置換基を
有していてもよく、フルキル基について一例を示せば、
フルコキシフルキル基、ハロフルキル基、アラルキル基
、ヒドロキシフェニル置倹フルキル基などが挙げられる
。また置換基を介して、数個のフェノール性化合物を分
子内に有していてもよい。As a substituent for Ar, a saturated or unsaturated furkyl group,
Dichlorofurkyl group, 7-lyl group, hydroxy group, alkoxy group, furkisthio group, 7-lyloxy group, arylthio group, halogen atom, dialkyl 7m8L carbonyl group, carboxyl group, carboxyl group, carbamoyl group, flukoxycarbonyl group, Preferable examples include a 7-syl group, a cyano group, a nitro group, a sulfonyl group, an isocyanate group, and a heterocyclic residue. These substituents may further have similar substituents; for example, for a furkyl group,
Examples include a flukoxyfurkyl group, a halofurkyl group, an aralkyl group, and a hydroxyphenyl-substituted furkyl group. Furthermore, the molecule may contain several phenolic compounds via substituents.
Arの置換基としては特に、メチル基、エチル基、イソ
プロピル基、t−ブチル基、ベンジル基、メトキシメチ
ル基、フェノキシメチル基、シクロヘキシル基、メトキ
シ基、エトキシ基、フェノキシメトキシ基、フェノキシ
エトキシ基、フェノキプロポキシ基、クロロエトキシ基
、メチルチオ基、エチルチオ基、フェニルチオエトキシ
基、フェノキシ基、ニルチオ基、フェノキシエチルチオ
基、アセチル基、7セトキシ基、メトキシカルボニル基
、ジアノ基、ホルミル基、トリフルオロメチル基、ジエ
チル7ミノ基、塩素原子、フッ素原子などが好ましい。In particular, substituents for Ar include methyl group, ethyl group, isopropyl group, t-butyl group, benzyl group, methoxymethyl group, phenoxymethyl group, cyclohexyl group, methoxy group, ethoxy group, phenoxymethoxy group, phenoxyethoxy group, Phenoxypropoxy group, chloroethoxy group, methylthio group, ethylthio group, phenylthioethoxy group, phenoxy group, nylthio group, phenoxyethylthio group, acetyl group, 7-cetoxy group, methoxycarbonyl group, diano group, formyl group, trifluoromethyl A diethyl 7-mino group, a chlorine atom, a fluorine atom, and the like are preferred.
上記−形式〔1〕中、nで示される整数2〜6が好まし
く、−(CH,)、−で示される2価の基は直鎖でも枝
分かれしていてもよい。In the above -format [1], n is preferably an integer of 2 to 6, and the divalent group represented by -(CH,) or - may be linear or branched.
本発明に係わるフルオラン誘導体の具体例を示すと、2
−7ニリノー3−メチル−6−N−エチル−N−(2−
フェノキシエチル)アミノフルオラン、2−7ニリノー
3−メチル−6−N−エチル−N−(3−フェノキシプ
ロピル)7ミノフルオラン、2−7ニリノー3−メチル
−6−N−エチル−N−(3−(4−メトキシフェノキ
シ)プロピル)7ミノフルオラン、2−7ニリノー3−
メチル−6−N−エチル−N−(3−(4−メチルチオ
フェノキシ)プロピル)アミノフルオラン褒2−7ニリ
ノー3−メチル−6−N−エチル−N−(3−L4−メ
トキシフェニルチオ)プロピル)アミノフルオラン、2
−7ニリノー3−メチル−6−N−エチル−N−(3−
(3−メチルフェノキシ)プロピル)7ミノワルオラン
、2−7二リノー3−メチル−6−N−エチル−N−〔
3−(3,5−ジフルオロフェノキシ)プロピル〕アミ
ノフルオラン、2−7ニリノー3−メチル−6−N−エ
チル−N−[3−(2−ナフチルオキシ)ブOピル〕7
ミノフルオラン、2−7ニリノー3−メチル−6−N−
エチル−N−(3−(4−(2−フェノキシエトキシ)
フェノキジンプロピル)アミノフルオラン、2−p−エ
チルアニリノ−3−メチル−6−N−エチル−N−(2
−(4−メトキシ−1−ナフチルオキシ)エチル〕7ミ
ノフルオラン、2−N−メチル−N−(3−トリフルオ
ロメチルフェニル)アミノフルオラン。Specific examples of the fluoran derivatives according to the present invention are as follows:
-7nilino3-methyl-6-N-ethyl-N-(2-
phenoxyethyl)aminofluorane, 2-7nilino3-methyl-6-N-ethyl-N-(3-phenoxypropyl)7minofluorane, 2-7nilino3-methyl-6-N-ethyl-N-(3 -(4-methoxyphenoxy)propyl)7minofluorane, 2-7nilino3-
Methyl-6-N-ethyl-N-(3-(4-methylthiophenoxy)propyl)aminofluorane 2-7nilino3-methyl-6-N-ethyl-N-(3-L4-methoxyphenylthio) propyl) aminofluorane, 2
-7nilino3-methyl-6-N-ethyl-N-(3-
(3-methylphenoxy)propyl) 7 minowalorane, 2-7 dilino 3-methyl-6-N-ethyl-N-
3-(3,5-difluorophenoxy)propyl]aminofluorane, 2-7nilino3-methyl-6-N-ethyl-N-[3-(2-naphthyloxy)butyl]7
Minofluorane, 2-7nilino-3-methyl-6-N-
Ethyl-N-(3-(4-(2-phenoxyethoxy))
phenoxidinepropyl)aminofluorane, 2-p-ethylanilino-3-methyl-6-N-ethyl-N-(2
-(4-methoxy-1-naphthyloxy)ethyl]7minofluorane, 2-N-methyl-N-(3-trifluoromethylphenyl)aminofluorane.
2−N−エチル−N−(2,4−ジメチル7ミノ)−6
−N−エチル−N−(3−(4−メチルチオフェノキシ
)ブOビル〕7ミノフルオラン。2-N-ethyl-N-(2,4-dimethyl7mino)-6
-N-Ethyl-N-(3-(4-methylthiophenoxy)buOvir]7minofluorane.
2−7ニリノー3−メチル−6−N−エチル−N−)2
− (4−(4−メトキシフェノキシ)フェノキシ)エ
チル)7ミノフルオラン、2−7ニリノー3−メチル−
6−N−エチル−N−(2−(2−メチルフェノキシ)
エチル)アミノフルオラン、2−7ニリノー3−メチル
−6−N−エチル−N−(2−(3−メチルフェノキシ
)エチル】アミノフルオラン、2−7ニリノー3−メチ
ル−5−N−エチル−N−(2−(4−メチルフェノキ
シ)エチル〕7ミノフルオラン、2−7二リノー3−メ
チル−5−N−エチル−N−(2−(2−エチルフェノ
キシ)エチル)7ミノフルオラン、2−7ニリノー3−
メチル−6−N−エチル−N−(2−(3−エチルフェ
ノキシ)エチルコアミノフルオラン、2−7ニリノー3
−メチル−6−N−エチル−N−(2−(4−エチルフ
ェノキシ)エチル)7ミノフルオラン、2−7ニリノー
3−メチル−6−N−エチル−N−(2−(2−メトキ
シフェノキシ)エチルコアミノフルオラン、2−7ニリ
ノー3−メチル−6−N−エチル−N−(2−(3−メ
トキシフェノキシ)エチル)アミノフルオラン、2−7
ニリノー3−メチル−6−N−エチル−N−(2−(4
−メトキシフェノキシ)エチル)アミノフルオラン、2
−7ニリノー3−メチル−6−N−エチル−N−(2−
(3,5−ジフルオO〕zノキシ)エチル)アミノフル
オラン、2−7ニリノー3−メチル−6−N−エチル−
N−(2−(4−フルオロフェノキシ)エチル)アミノ
フルオラン、2−7ニリノー3−メチル−6−N−エチ
ル−N−(2−(4−りOロフェノキシ)エチル)アミ
ノフルオラン、2−7ニリノー3−メチル−6−N−エ
チル−N−(2−(4−メチルチオフェノキシ)エチル
)7ミノフルオラン、2−7ニリノー3−メチル−6−
N−エチルートー(2−(4−エチルチオフェノキシ)
エチル)アミノフルオラン。2-7nilino3-methyl-6-N-ethyl-N-)2
- (4-(4-methoxyphenoxy)phenoxy)ethyl)7minofluorane, 2-7nilino3-methyl-
6-N-ethyl-N-(2-(2-methylphenoxy)
ethyl)aminofluorane, 2-7nilino3-methyl-6-N-ethyl-N-(2-(3-methylphenoxy)ethyl)aminofluorane, 2-7nilino3-methyl-5-N-ethyl -N-(2-(4-methylphenoxy)ethyl)7minofluorane, 2-7dilino3-methyl-5-N-ethyl-N-(2-(2-ethylphenoxy)ethyl)7minofluorane, 2- 7 Nilino 3-
Methyl-6-N-ethyl-N-(2-(3-ethylphenoxy)ethylcoaminofluorane, 2-7 Nilino 3
-Methyl-6-N-ethyl-N-(2-(4-ethylphenoxy)ethyl)7minofluorane, 2-7nilino3-methyl-6-N-ethyl-N-(2-(2-methoxyphenoxy)) Ethylcoaminofluorane, 2-7 Nilino 3-methyl-6-N-ethyl-N-(2-(3-methoxyphenoxy)ethyl)aminofluorane, 2-7
Nilino 3-methyl-6-N-ethyl-N-(2-(4
-methoxyphenoxy)ethyl)aminofluorane, 2
-7nilino3-methyl-6-N-ethyl-N-(2-
(3,5-difluoro[znoxy)ethyl)aminofluorane, 2-7nilino3-methyl-6-N-ethyl-
N-(2-(4-fluorophenoxy)ethyl)aminofluorane, 2-7nilino-3-methyl-6-N-ethyl-N-(2-(4-fluorophenoxy)ethyl)aminofluorane, 2-7 Nilino 3-methyl-6-N-ethyl-N-(2-(4-methylthiophenoxy)ethyl)7minofluorane, 2-7 Nilino 3-methyl-6-
N-ethylthio(2-(4-ethylthiophenoxy)
ethyl) aminofluorane.
2−7ニリノー3−メチル−6−N−エチル−N−(4
−(4−エチルフェノキ)ブチル〕7ミノフルオラン、
2−7ニリノー3−メチル−6−N−エチルーN−(1
−メチル−2−フェノキシエチル)アミノフルオラン、
2−7ニリノー3−メチル−6−N−エチル−N−(4
−(4−メトキシフェノキシ)ブチル〕7ミノフルオラ
ン、2−7ニリノー3−メチル−6−N−エチル−N−
(4−(3−メチルフェノキシ)ブチル)アミノフルオ
ラン、2−7ニリノー3−メチル−6−N−エチル−N
−(2−(2−メチルフェノキシ)エチル)7ミノフル
オラン、2−7ニリノー3−メチル−6−N−エチル−
N−(2−(2−メチルフェノキシ)エチルコアミノフ
ルオラン、2−p−エチル7ニリノー3−メチル−6−
N−エチル−N−(2−(4−エチルフェノキシ)エチ
ル)7ミノフルオラン、2−N−メチル−N−(3−ト
リフルオロメチルフェニル)7ミノー6−N−エチル−
N−(2−(2−エチルフェノキシ)エチル)アミノフ
ルオラン、2−エチル−(2,4−ジメチルフェニル)
7ミノー6−N−(2−(4−メトキシフェノキシ)エ
チル)7ミノフルオラン、2−7ニリノー3−メチル−
6−N−テトラヒドロフルフリル−N−(2−(4−エ
チルフェノキシ)エチル〕7ミノフルオラン。2-7 Nilino 3-methyl-6-N-ethyl-N-(4
-(4-ethylphenoxy)butyl]7minofluorane,
2-7 Nilino 3-methyl-6-N-ethyl-N-(1
-methyl-2-phenoxyethyl)aminofluorane,
2-7 Nilino 3-methyl-6-N-ethyl-N-(4
-(4-methoxyphenoxy)butyl]7minofluorane, 2-7nilino3-methyl-6-N-ethyl-N-
(4-(3-methylphenoxy)butyl)aminofluorane, 2-7nilino-3-methyl-6-N-ethyl-N
-(2-(2-methylphenoxy)ethyl)7minofluorane, 2-7nilino3-methyl-6-N-ethyl-
N-(2-(2-methylphenoxy)ethylcoaminofluorane, 2-p-ethyl7nilino3-methyl-6-
N-ethyl-N-(2-(4-ethylphenoxy)ethyl)7minofluorane, 2-N-methyl-N-(3-trifluoromethylphenyl)7mino6-N-ethyl-
N-(2-(2-ethylphenoxy)ethyl)aminofluorane, 2-ethyl-(2,4-dimethylphenyl)
7 minnow 6-N-(2-(4-methoxyphenoxy)ethyl) 7 minofluorane, 2-7 nilino 3-methyl-
6-N-tetrahydrofurfuryl-N-(2-(4-ethylphenoxy)ethyl)7minofluorane.
2−7ニリノー3−メチル−6−N−トリル−N−(2
−(4−エチルフェノキシ)エチル】7ミノフルオラン
、2−7ニリノー3−メチル−6−N−シフOへキシル
−N−(2−(4−エチルフェノキシ)エチル)アミノ
フルオラン、2−7二リノー3−メトキシ−6−N−エ
チル−N−(2−(4−エチルフェノキシ)エチル)7
ミノフルオラン、2−7ニリノー3−クロロ−6−N−
エチル−N−(2−(4−エチルフェノキシ)エチル〕
7ミノフルオラン、2−7ニリノー3−n−へキシル−
6−N−エチル−N−(2−(4−エチルフェノキシ)
エチル)アミノフルオラン、2−(2,4−ジメチル)
アニリノ−3−メチ ルー6−N−エチル−N−(3−
(4−エチルフェノキシ)エチル)7ミノフルオラン、
2−o−フルオロ7ニリノー3−メチル−6−N−エチ
ル−N−(3−(4−エチルフェノキシ)ブOピル〕ア
ミノフルオラン+2 o−クロロ7ニリノー3−メチ
ル−6−N−エチル−N−(3−(4−エチルフェノキ
シ)ブOピル〕7ミノフルオラン。2-7 Nilino 3-methyl-6-N-tolyl-N-(2
-(4-ethylphenoxy)ethyl]7minofluorane, 2-7nilino3-methyl-6-N-SchifOhexyl-N-(2-(4-ethylphenoxy)ethyl)aminofluorane, 2-7 Rino-3-methoxy-6-N-ethyl-N-(2-(4-ethylphenoxy)ethyl)7
Minofluorane, 2-7nilino-3-chloro-6-N-
Ethyl-N-(2-(4-ethylphenoxy)ethyl)
7minofluorane, 2-7nilino-3-n-hexyl-
6-N-ethyl-N-(2-(4-ethylphenoxy)
ethyl)aminofluorane, 2-(2,4-dimethyl)
Anilino-3-methyl-6-N-ethyl-N-(3-
(4-ethylphenoxy)ethyl)7minofluorane,
2-o-fluoro7nilino3-methyl-6-N-ethyl-N-(3-(4-ethylphenoxy)buOpyr)aminofluorane+2 o-chloro7nilino3-methyl-6-N-ethyl -N-(3-(4-ethylphenoxy)buOpyr)7minofluorane.
2−7ニリノー3−メチル−6−N−エチル−N−(2
−フェノキシプロビル)7ミノフルオランなどが挙げら
れる。2-7 Nilino 3-methyl-6-N-ethyl-N-(2
-phenoxyprovir) 7minofluorane, and the like.
本発明に係わる電子供与性無色染料は従来より公知のト
リフェニルメタン系化合物、フルオラン系化合物、フェ
ノチアジン系化合物、インドリルフタリド系化合物、ロ
イコオーラミン系化合物、ローダミンラクタム系化合物
、トリフェニルメタン系化合物、トリアゼン系化合物、
スピロピラン系化合物、フルオレン系化合物など各種の
化合物と併用できる。The electron-donating colorless dyes according to the present invention include conventionally known triphenylmethane compounds, fluoran compounds, phenothiazine compounds, indolylphthalide compounds, leucoauramine compounds, rhodamine lactam compounds, and triphenylmethane compounds. compounds, triazene compounds,
It can be used in combination with various compounds such as spiropyran compounds and fluorene compounds.
フタリド類の具体例は米国特許再発行特許明細1i第2
3024号、米国特許明細書第3491111号、同第
3491112号、同第3491116号及び同第35
09174号、フルオラン類の具体例は米国特許明細書
第3624107号、同第3627787号、同第36
41011号、同第3462828号、同第36813
90号、同第3920510号、同第3959571号
、スピロピラン類の具体例は米国特許明細第39718
08号、ピリジン系及びピラジン系化合物類は米国特許
明細書第3776424号、同第3853869号、同
第4246318号、フルオラン系化合物の具体例は特
願昭61−240989号等に記載されている。Specific examples of phthalides are given in U.S. Patent Reissue Patent Specification 1i No. 2.
No. 3024, US Pat. No. 3,491,111, US Pat. No. 3,491,112, US Pat.
No. 09174, specific examples of fluorans are U.S. Patent Specifications No. 3,624,107, U.S. Pat.
No. 41011, No. 3462828, No. 36813
No. 90, No. 3920510, No. 3959571, and specific examples of spiropyrans are U.S. Patent Specification No. 39718.
No. 08, pyridine-based and pyrazine-based compounds are described in US Pat. No. 3,776,424, US Pat. No. 3,853,869, and US Pat.
本発明に係わる電子受容性化合物化合物はフェノール誘
導体、芳香族カルボン酸の金属塩、酸性白土、ベントナ
イト、ノボラック樹脂、金属処理ノボラック樹脂、金属
錯体などが用いられる。これらの例は特公昭40−93
09号、特公昭45−14039号、特開昭52−14
0483号、特開昭48−51510号、特開昭57−
210886号、特開昭58−87089号、特開昭5
9−11286号、特開昭60−176795号、特開
昭61−95988号等に記載されている。The electron-accepting compound used in the present invention includes phenol derivatives, metal salts of aromatic carboxylic acids, acid clay, bentonite, novolac resins, metal-treated novolac resins, metal complexes, and the like. These examples are
No. 09, JP 45-14039, JP 52-14
No. 0483, JP-A-48-51510, JP-A-57-
No. 210886, JP-A-58-87089, JP-A-Sho 5
9-11286, JP-A-60-176795, JP-A-61-95988, etc.
これらの一部を例示すれば、フェノール性化合物として
は、2.2’−ビス(4−ヒドロキシフェニル)プロパ
ン、4−フェニルフェノール、1,1− ビス(3−ク
ロo−4−ヒドロキシフェニル) シクロヘキサン、1
.1− ビス(4−ヒドロキシフェニル)シクロヘキサ
ン、1,1− ビス(3−クロロ−4−ヒドロキシフェ
ニル)−2−エチルブタン、4.4″−5ec−インオ
クチリデンジフェノール、4,4′−5ec−ブチリデ
ンジフェノール、4−p−メチルフェニルフェノール、
4.4′−メチルシフOへキシリデンフェノール、4゜
4′−イソペンチリデンフェノール、ビス(3−7リー
ルー4−ヒドロキシフェニル)スルホン、4−ヒドロキ
シフェニル−3゛4° ジメチルフェニルスルホン、4
−(4−イソブOボキシフェニルスルホニル)フェノー
ル、ビス(2−(4−ヒドロキシフェニルチオ)エトキ
シ)メタン、P−ヒトOキシ安息香酸ベンジル等がある
。サリチル酸誘導体としては4−ペンタデシルサリチル
酸、3,5−ジ(α−メチルベンジル)サリチル酸、3
.5−ジ(ter−オクチル)サリチル酸、5−α−(
p−α−メチルベンジルフェニル) エチルサリチル酸
、3−α−メチルベンジル−5−tar−オクチルサリ
チル酸、5−テトラデシルサリチル酸、4−へキシルオ
キシサリチル酸、4−シフOへキシルオキシサリチル酸
、4−デシルオキシサリチル酸、4−ドデシルオキシサ
リチル酸、4−ペンタデシルオキシサリチル酸、4−オ
クタデシルオキシサリチル酸等、及びこれらの亜鉛、ア
ルミニウム、カルシウム、銅等の塩がある。これらのう
ちビスフェノール類が好ましい。To give some examples of these, phenolic compounds include 2,2'-bis(4-hydroxyphenyl)propane, 4-phenylphenol, and 1,1-bis(3-chloroo-4-hydroxyphenyl). Cyclohexane, 1
.. 1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(3-chloro-4-hydroxyphenyl)-2-ethylbutane, 4.4″-5ec-inoctylidene diphenol, 4,4′-5ec -butylidene diphenol, 4-p-methylphenylphenol,
4.4'-Methylschif-O hexylidenephenol, 4゜4'-isopentylidenephenol, bis(3-7ly-4-hydroxyphenyl)sulfone, 4-hydroxyphenyl-3゛4° dimethylphenylsulfone, 4
-(4-isobuOboxyphenylsulfonyl)phenol, bis(2-(4-hydroxyphenylthio)ethoxy)methane, benzyl P-humanOoxybenzoate, and the like. Salicylic acid derivatives include 4-pentadecylsalicylic acid, 3,5-di(α-methylbenzyl)salicylic acid, 3
.. 5-di(ter-octyl)salicylic acid, 5-α-(
p-α-methylbenzylphenyl) ethylsalicylic acid, 3-α-methylbenzyl-5-tar-octylsalicylic acid, 5-tetradecylsalicylic acid, 4-hexyloxysalicylic acid, 4-SchiffO hexyloxysalicylic acid, 4-decyl Examples include oxysalicylic acid, 4-dodecyloxysalicylic acid, 4-pentadecyloxysalicylic acid, 4-octadecyloxysalicylic acid, and their salts such as zinc, aluminum, calcium, and copper. Among these, bisphenols are preferred.
本発明に係わるアミド化合物は下記一般式(11) で
表され、ウレア化合物は下記一般式(III)で表され
る。The amide compound according to the present invention is represented by the following general formula (11), and the urea compound is represented by the following general formula (III).
RI CON HR2(II)
R3−NHCONH2(II+)
(RI R3は置換基があってもよいアルキル基、
R3は水素原子またはフエ平ル基、R4はアルキル基で
あり、フェニル基でIIされていても良く、nは1〜5
の整数を示す。)
一般式(11)〜(IV)の具体例としてはメチロール
ステアリルアミド、ステアリン酸アミド、パルミチン酸
アミド、テトラコハク酸アミド、N−フェニルステアリ
ン酸アミド、N−フェニルパルミチン酸アミド、N−ス
テアリル尿素、N−バルミチル尿素、p−ベンジルビフ
ェニルなどがあげられる。RI CON HR2 (II) R3-NHCONH2 (II+) (RI R3 is an alkyl group that may have a substituent,
R3 is a hydrogen atom or a phenyl group, R4 is an alkyl group, which may be a phenyl group, and n is 1 to 5.
indicates an integer. ) Specific examples of general formulas (11) to (IV) include methylolstearylamide, stearic acid amide, palmitic acid amide, tetrasuccinic acid amide, N-phenylstearic acid amide, N-phenylpalmitic acid amide, N-stearylurea, Examples include N-balmitylurea and p-benzylbiphenyl.
次に本発明の代表的感熱発色層の製法について述べる。Next, a typical method for producing a heat-sensitive coloring layer of the present invention will be described.
電子供与性無色染料、電子受容性化合物、増感剤は、ポ
リビニールアルコール等の水溶性高分子水溶液とともに
ボールミル、サンドミル等を用い数ミクロン以下まで分
散される。増感剤は、電子供与性無色染料、電子受容性
化合物のいずれ、または両方に加え、同時に分散するか
、場合によっては予め電子供与性無色染料ないし電子受
容性化合物との共融物を作成し、分散しても良い。The electron-donating colorless dye, the electron-accepting compound, and the sensitizer are dispersed to a size of several microns or less together with an aqueous solution of a water-soluble polymer such as polyvinyl alcohol using a ball mill, sand mill, or the like. The sensitizer is added to either the electron-donating colorless dye or the electron-accepting compound, or both, and is dispersed simultaneously, or in some cases, a eutectic product is prepared in advance with the electron-donating colorless dye or the electron-accepting compound. , may be dispersed.
これらの分散物は、分散後混合され、必要に応じ顔料、
界面活性剤、バインダー、金属石鹸、ワックス、酸化防
止剤、紫外線吸収剤等を加え感熱塗液とする。得られた
感熱塗液は、上質紙、下塗り層を有する上質紙、合成紙
、プラスチックフィルム等に塗布乾燥された後、キャレ
ンダー処理により平滑性を付与し、目的の感熱記録材料
となる。These dispersions are mixed after dispersion, and pigments and
Add surfactant, binder, metal soap, wax, antioxidant, ultraviolet absorber, etc. to make a heat-sensitive coating liquid. The obtained heat-sensitive coating liquid is coated and dried on high-quality paper, high-quality paper with an undercoat layer, synthetic paper, plastic film, etc., and then smoothed by calendering to obtain the desired heat-sensitive recording material.
この際、JIS−8119で規定される平滑度が500
秒以上、特に、800秒以上の支持体を用いるのがドツ
ト再現性の点から特に好ましい。平滑度が500秒以上
の支持体を得るには、■ 合成紙やプラスチックフィル
ムのような平滑度の高いものを使用する
■ 支持体上に顔料を主成分とする下塗り層を設ける
■ スーパーキャレンダー等を使用し支持体の平滑度を
高くする
等の手段がある。At this time, the smoothness specified by JIS-8119 is 500.
From the viewpoint of dot reproducibility, it is particularly preferable to use a support that lasts for at least 80 seconds, particularly for at least 800 seconds. To obtain a support with a smoothness of 500 seconds or more, ■ Use something with high smoothness such as synthetic paper or plastic film ■ Provide an undercoat layer containing pigment as the main component on the support ■ Super Calender There are methods such as increasing the smoothness of the support by using .
バインダーとしては、25℃の水に対して5重量%以上
溶解する化合物が好ましく、具体的には、ポリビニルア
ルコール(カルボキシ変性、イタコン酸変性、マレイン
酸変性、シリカ変性等の変性ポリビニルアルコールを含
む)、メチルセルロース、カルボキシメチルセルロース
、デンプン類(変性デンプンを含む)、ゼラチン、アラ
ビアゴム、カゼイン、スチレン−無水マレイン酸共重合
体加水分解物、ポリアクリルアミド、酢酸ビニル−ポリ
アクリル酸共重合体の鹸化物等があげられる。これらの
バインダーは分散時のみならず、塗膜強度を向上させる
目的で使用されるが、この目的に対してはスチレン・ブ
タジェン共重合物、酢酸ビニル共重合物、7クリロニト
リル・ブタジェン共重合物、アクリル酸メチル・ブタジ
ェン共重合物、ポリ塩化ビニリデンのごとき合成高分子
のラテックス系のバインダーを併用することもできる。The binder is preferably a compound that dissolves 5% by weight or more in water at 25°C, and specifically, polyvinyl alcohol (including modified polyvinyl alcohols such as carboxy-modified, itaconic acid-modified, maleic acid-modified, and silica-modified polyvinyl alcohols). , methylcellulose, carboxymethylcellulose, starches (including modified starches), gelatin, gum arabic, casein, styrene-maleic anhydride copolymer hydrolyzate, polyacrylamide, saponified vinyl acetate-polyacrylic acid copolymer, etc. can be given. These binders are used not only for dispersion but also for the purpose of improving coating film strength. , methyl acrylate-butadiene copolymer, and synthetic polymer latex binder such as polyvinylidene chloride can also be used in combination.
また、必要に応じこれらバインダーの種類に応じて、適
当なバインダーの架橋剤を添加しても良い。Further, a crosslinking agent suitable for the binder may be added depending on the type of the binder, if necessary.
顔料としては、炭酸カルシウム、硫酸バリウム、リトポ
ン、ロウ石、カオリン、シリカ、非晶質シリカなどがあ
る。Pigments include calcium carbonate, barium sulfate, lithopone, waxite, kaolin, silica, amorphous silica, and the like.
金属石鹸としては、高級脂肪酸金属塩が用いられ、ステ
アリン酸亜鉛、ステアリン酸カルシウム、ステアリン酸
アルミニウムなどが用いられる。As the metal soap, higher fatty acid metal salts are used, such as zinc stearate, calcium stearate, aluminum stearate, and the like.
更に必要に応じて界面活性剤、帯電防止剤、紫外線吸収
剤、消泡剤、導電剤、蛍光染料、着色染料などを添加し
てもよい。Furthermore, surfactants, antistatic agents, ultraviolet absorbers, antifoaming agents, conductive agents, fluorescent dyes, coloring dyes, etc. may be added as necessary.
塗布された感熱記録材料は乾燥されキャレンダー等の処
理をほどこして使用に供される。The coated heat-sensitive recording material is dried and subjected to a process such as a calender before being used.
また、必要に応じて感熱発色層の上に保護層を設けても
良い。保護層は感熱記録材料の保護層として公知の物で
あればいづれのものでも使用することができる。Further, a protective layer may be provided on the heat-sensitive coloring layer if necessary. As the protective layer, any one known as a protective layer for heat-sensitive recording materials can be used.
さらに、必要に応じて感熱記録材料の支持体の感熱発色
層とは反対の面にバックコート層を設けても良い。バッ
クコート層はr熱記録材料のバックコート層として公知
の物であればいずれのものでも使用することができる。Furthermore, if necessary, a back coat layer may be provided on the opposite side of the support of the heat-sensitive recording material from the heat-sensitive coloring layer. As the back coat layer, any material known as a back coat layer for thermal recording materials can be used.
以下実施例を示し本発明を具体的に説明するが、本発明
は以下実施例のみに限定されるものではない。EXAMPLES The present invention will be specifically explained below with reference to Examples, but the present invention is not limited only to the Examples below.
(実施例−1)
電子供与性無色染料として 2−7ニリノー3−メチル
−6−N−エチル−N−(3−メチルフェノキシプロピ
ル)7ミノフルオラン電子受容性化合物としてビスフェ
ノールA、熱可融性化合物としてメチロールステ7リル
アミド、各々209を1009の5%ポリビニルアルコ
ール(クラレ PVA−105)水溶液と共に一昼夜ボ
ールミルで分散し、平均粒径を1.5μm以下にし、各
々の分散液を得た。また、炭酸カルシウム809をヘキ
サメタリン酸ソーダ0.5%溶液1609と共にホモジ
ナイザーで分散し、顔料分散液を得た。(Example-1) 2-7nilino3-methyl-6-N-ethyl-N-(3-methylphenoxypropyl)7minofluoran as an electron-donating colorless dye Bisphenol A as an electron-accepting compound, a thermofusible compound Each of methylolster-7lylamide and 209 was dispersed with a 5% aqueous solution of polyvinyl alcohol (Kuraray PVA-105) of 1009 in a ball mill for one day and night, and the average particle size was adjusted to 1.5 μm or less to obtain each dispersion. Further, calcium carbonate 809 was dispersed with a 0.5% sodium hexametaphosphate solution 1609 using a homogenizer to obtain a pigment dispersion.
以上のようにして作成した各分散液を電子供与性無色染
料分散液59、電子受容性化合物分散液109、β−ナ
フチルベンジルエーテル分散液109、炭酸カルシウム
分散液を59の割合で混合しさらに21%ステアリン酸
亜鉛エマルジョン39を添加して感熱塗液を得た。この
感熱発色層塗布液を坪量509/m2の上質紙上にワイ
ヤーバーを用いて塗布層の乾燥重置が59フイになるよ
うに塗布し、50℃で1分間乾燥して感熱記録紙を得た
。Each of the dispersions prepared as described above was mixed with 59 parts of an electron-donating colorless dye dispersion, 109 parts of an electron-accepting compound dispersion, 109 parts of a β-naphthylbenzyl ether dispersion, and 59 parts of a calcium carbonate dispersion. A heat-sensitive coating liquid was obtained by adding 39% zinc stearate emulsion. This heat-sensitive coloring layer coating solution was applied onto a high-quality paper with a basis weight of 509/m2 using a wire bar so that the dry overlap of the coated layer was 59 ft, and was dried at 50°C for 1 minute to obtain heat-sensitive recording paper. Ta.
(実施例−2)
実施例−1のメチロールステアリルアミドの代わりに、
ステアリル尿素を使用した以外は実施例−1と同様に感
熱記録材料を得た。(Example-2) Instead of methylolstearylamide in Example-1,
A heat-sensitive recording material was obtained in the same manner as in Example-1 except that stearyl urea was used.
(実施例−3)
実施例−1のメチロールステアリルアミドの代わりに、
p−ベンジルビフェニルを用いて感熱塗液を調製した以
外は同様の方法により感熱記録紙を得た。(Example-3) Instead of methylolstearylamide in Example-1,
A heat-sensitive recording paper was obtained in the same manner except that p-benzylbiphenyl was used to prepare the heat-sensitive coating liquid.
(実施例−4)
実施例−1の2−7ニリノー3−メチル−6−N−(4
−メトキシフェノキシプロピル)アミノフルオランの代
わりに、2−7ニリノー3−メチル−6−N−エチル−
N−(3−メチルフェノキシプロピル)アミノフルオラ
ンを用いた以外は実施例−1と同様にして感熱記録材料
を得た。(Example-4) 2-7nilino-3-methyl-6-N-(4
-methoxyphenoxypropyl)aminofluorane instead of 2-7nilino3-methyl-6-N-ethyl-
A heat-sensitive recording material was obtained in the same manner as in Example 1 except that N-(3-methylphenoxypropyl)aminofluorane was used.
(比較例−1)
実施例−1のメチロールステ7リルアミドを使用しなか
った以外は実施例〒1と同様の方法により感熱記録材料
を得た。(Comparative Example-1) A heat-sensitive recording material was obtained in the same manner as in Example 1, except that the methylolster-7-lylamide of Example 1 was not used.
(比較例−2)
実施例−1の2−7ニリノー3−メチル−6−N−エチ
ル−N−(4−メトキシフェノキシプロピル)7ミノフ
ルオランの代わりに、2−7ニリノー3−メチル−6−
ジニチル7ミノフルオランを使用した以外は実施例−1
と同様にして感熱記録材料を得た。(Comparative Example-2) Instead of 2-7nilino-3-methyl-6-N-ethyl-N-(4-methoxyphenoxypropyl)7minofluorane in Example-1, 2-7nilino-3-methyl-6-
Example-1 except that dinityl 7minofluorane was used
A heat-sensitive recording material was obtained in the same manner as above.
(比較例−3)
実施例−1のメチロールステフリルアミドの代わりにp
−ヒドロキシメチルベンジルエステルを使用した以外は
実施例−1と同様にして感熱記録材料を得た。(Comparative Example-3) In place of methylolstefurylamide in Example-1, p
A heat-sensitive recording material was obtained in the same manner as in Example-1 except that -hydroxymethylbenzyl ester was used.
以上のようにして得られた感熱記録紙を、キャレンダー
で表面処理し、平滑度がベック平滑度として300±5
0秒になるよう調整し、感熱記録材料を得た。The surface of the thermal recording paper obtained as described above was treated with a calender, and the smoothness was 300±5 as Beck smoothness.
The temperature was adjusted to 0 seconds to obtain a heat-sensitive recording material.
感熱記録紙の評価は以下の様に行った。The thermal recording paper was evaluated as follows.
■発色濃度は京セラ製印字試験機で印字エネルギー30
mJ/mm’ でEl1字し発色濃度をマクベス濃度計
で測定した。この値が高いほうが、感熱記録紙の感度が
高い。■Color density was determined by Kyocera printing tester at printing energy of 30.
The color density was measured using a Macbeth densitometer using mJ/mm'. The higher this value is, the higher the sensitivity of the thermal recording paper is.
■耐熱性評価は、60”030%RHで24時間放置後
の、白地部の濃度および発色濃度が1.3の印字部(京
セラ製印字試験機で印字)の濃度をマクベス濃度計で測
定した。白地部の濃度が低く、印字部の濃度が高いもの
が、保存性が高い。■For heat resistance evaluation, the density of the white background area and the density of the printed area (printed with a Kyocera printing tester) with a color development density of 1.3 were measured using a Macbeth densitometer after being left at 60" 30% RH for 24 hours. .Those with low density in the white background area and high density in the printed area have a high shelf life.
■耐薬品性評価は、エタノールQ、lccをスポイトで
感熱記録材料上に滴下し、カブリを目視で以下のように
評価した。(2) For chemical resistance evaluation, ethanol Q, LCC was dropped onto the heat-sensitive recording material using a dropper, and fogging was visually evaluated as follows.
Q カブリが発生していない
x カブリが発生している
第1表
表の結果かられかるように、本発明の感熱記録材料は高
感度で高温度保管状態における白地部および印字部の保
存性く、耐薬品性も良好な感熱記録材料であることがわ
かる。Q: No fogging: x: Fogging: As can be seen from the results in Table 1, the heat-sensitive recording material of the present invention has high sensitivity, and the storage stability of the white background area and printed area under high temperature storage conditions. It can be seen that this is a heat-sensitive recording material with good chemical resistance.
Claims (1)
合物を含有してなる感熱記録材料において、該電子供与
性無色染料として6位にアリールオキシ基またはアリー
ルチオ基で置換されたアルキルアミノ基を有するフルオ
ラン誘導体を含有し、かつ熱可融性化合物として芳香環
及び/又はアミド及び/又はウレアを含む炭化水素化合
物を少なくとも1種以上含有することを特徴とする感熱
記録材料。In a heat-sensitive recording material containing an electron-donating colorless dye, an electron-accepting compound, and a thermofusible compound, the electron-donating colorless dye has an alkylamino group substituted with an aryloxy group or an arylthio group at the 6-position. 1. A heat-sensitive recording material characterized in that it contains a fluoran derivative having the following properties, and at least one hydrocarbon compound containing an aromatic ring and/or amide and/or urea as a thermofusible compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2156682A JPH0447988A (en) | 1990-06-15 | 1990-06-15 | Thermal recording material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2156682A JPH0447988A (en) | 1990-06-15 | 1990-06-15 | Thermal recording material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0447988A true JPH0447988A (en) | 1992-02-18 |
Family
ID=15633023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2156682A Pending JPH0447988A (en) | 1990-06-15 | 1990-06-15 | Thermal recording material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0447988A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19822763B4 (en) * | 1997-10-31 | 2007-05-03 | Mitsubishi Denki K.K. | Power semiconductor device and manufacturing method of a power semiconductor device |
-
1990
- 1990-06-15 JP JP2156682A patent/JPH0447988A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19822763B4 (en) * | 1997-10-31 | 2007-05-03 | Mitsubishi Denki K.K. | Power semiconductor device and manufacturing method of a power semiconductor device |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH07149044A (en) | Thermal recording material | |
| JPH0447988A (en) | Thermal recording material | |
| JPH0447987A (en) | Thermal recording material | |
| JPH0410977A (en) | Thermal recording material | |
| JPH1016402A (en) | Heat-sensitive recording material | |
| JPH0486288A (en) | Thermal recording material | |
| JPH0486287A (en) | Thermal recording material | |
| JPH03182388A (en) | Thermal recording material | |
| JPH06171233A (en) | Thermosensible recording material | |
| JPH0486286A (en) | Thermal recording material | |
| JPH02215585A (en) | Recording material | |
| JPH02223474A (en) | Heat-sensitive recording material | |
| JPH0410978A (en) | Thermal recording material | |
| JP2672183B2 (en) | Thermal recording material | |
| JPH07149045A (en) | Thermal recording material | |
| JPH054449A (en) | Heat-sensitive recording material | |
| JPH04135788A (en) | Thermal recording material | |
| JPS60178086A (en) | Thermal recording material | |
| JPH03292186A (en) | heat sensitive recording material | |
| JPH04122683A (en) | Thermal recording material | |
| JPH0321489A (en) | Thermal recording material | |
| JPH0732747A (en) | Heat-sensitive recording material | |
| JPH0270481A (en) | Thermal recording material | |
| JP2000118148A (en) | Thermal recording medium | |
| JPH03288691A (en) | Thermal recording material |