JPH04156381A - Thermally sensitive material - Google Patents
Thermally sensitive materialInfo
- Publication number
- JPH04156381A JPH04156381A JP2279310A JP27931090A JPH04156381A JP H04156381 A JPH04156381 A JP H04156381A JP 2279310 A JP2279310 A JP 2279310A JP 27931090 A JP27931090 A JP 27931090A JP H04156381 A JPH04156381 A JP H04156381A
- Authority
- JP
- Japan
- Prior art keywords
- heat
- liquid
- sensitivity
- compound
- recording layer
- 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 15
- 239000011230 binding agent Substances 0.000 claims abstract description 11
- -1 benzene compound Chemical class 0.000 claims abstract description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000126 substance Substances 0.000 claims abstract description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 18
- 230000035945 sensitivity Effects 0.000 abstract description 14
- 238000002844 melting Methods 0.000 abstract description 7
- 230000008018 melting Effects 0.000 abstract description 7
- 238000003860 storage Methods 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 4
- 238000004040 coloring Methods 0.000 abstract description 4
- 238000006467 substitution reaction Methods 0.000 abstract 2
- 239000007788 liquid Substances 0.000 description 29
- 239000003973 paint Substances 0.000 description 11
- 238000011161 development Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 9
- 239000000975 dye Substances 0.000 description 7
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 239000004372 Polyvinyl alcohol Substances 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000002220 fluorenes Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- BMOAQMNPJSPXIU-UHFFFAOYSA-N ethyl 2-(3-fluoro-4-nitrophenyl)propanoate Chemical compound CCOC(=O)C(C)C1=CC=C([N+]([O-])=O)C(F)=C1 BMOAQMNPJSPXIU-UHFFFAOYSA-N 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 150000004893 oxazines Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229940043267 rhodamine b Drugs 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 150000004897 thiazines Chemical class 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- WAOCEEXLEFNWKA-UHFFFAOYSA-N (4-chlorophenyl)methyl 4-hydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OCC1=CC=C(Cl)C=C1 WAOCEEXLEFNWKA-UHFFFAOYSA-N 0.000 description 1
- BYFJLAHGKYACPI-UHFFFAOYSA-N (4-methylphenyl)methyl 4-hydroxybenzoate Chemical compound C1=CC(C)=CC=C1COC(=O)C1=CC=C(O)C=C1 BYFJLAHGKYACPI-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical class C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- SXUHHYZFGARGGI-UHFFFAOYSA-N 1,4-dibenzyl-2,5-dimethoxybenzene Chemical compound COC=1C=C(CC=2C=CC=CC=2)C(OC)=CC=1CC1=CC=CC=C1 SXUHHYZFGARGGI-UHFFFAOYSA-N 0.000 description 1
- GVTXARZQXQLUBQ-UHFFFAOYSA-N 1,4-dibenzyl-2,5-dimethylbenzene Chemical group CC=1C=C(CC=2C=CC=CC=2)C(C)=CC=1CC1=CC=CC=C1 GVTXARZQXQLUBQ-UHFFFAOYSA-N 0.000 description 1
- BKFBBDCOHSXATN-UHFFFAOYSA-N 1-[3,7-bis(diethylamino)phenoxazin-10-yl]ethanone Chemical compound C1=C(N(CC)CC)C=C2OC3=CC(N(CC)CC)=CC=C3N(C(C)=O)C2=C1 BKFBBDCOHSXATN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QWQJPPOEEGYTIW-UHFFFAOYSA-N 1-fluoro-1-phenylhydrazine Chemical compound NN(F)C1=CC=CC=C1 QWQJPPOEEGYTIW-UHFFFAOYSA-N 0.000 description 1
- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 description 1
- DXYZIGZCEVJFIX-UHFFFAOYSA-N 2'-(dibenzylamino)-6'-(diethylamino)spiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound C=1C(N(CC)CC)=CC=C(C2(C3=CC=CC=C3C(=O)O2)C2=C3)C=1OC2=CC=C3N(CC=1C=CC=CC=1)CC1=CC=CC=C1 DXYZIGZCEVJFIX-UHFFFAOYSA-N 0.000 description 1
- PKKDWPSOOQBWFB-UHFFFAOYSA-N 2,4-dichloro-6-[(3,5-dichloro-2-hydroxyphenyl)methyl]phenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1CC1=CC(Cl)=CC(Cl)=C1O PKKDWPSOOQBWFB-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- XGAYQDWZIPRBPF-UHFFFAOYSA-N 2-hydroxy-3-propan-2-ylbenzoic acid Chemical compound CC(C)C1=CC=CC(C(O)=O)=C1O XGAYQDWZIPRBPF-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
- 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
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
- NMWKWBPNKPGATC-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2-benzofuran-1(3H)-one Chemical compound ClC1=C(Cl)C(Cl)=C2COC(=O)C2=C1Cl NMWKWBPNKPGATC-UHFFFAOYSA-N 0.000 description 1
- JSUKRBMPOXGCPR-UHFFFAOYSA-N 4-(benzenesulfonyl)phenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=CC=C1 JSUKRBMPOXGCPR-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- NJESAXZANHETJV-UHFFFAOYSA-N 4-methylsalicylic acid Chemical compound CC1=CC=C(C(O)=O)C(O)=C1 NJESAXZANHETJV-UHFFFAOYSA-N 0.000 description 1
- XURABDHWIADCPO-UHFFFAOYSA-N 4-prop-2-enylhepta-1,6-diene Chemical class C=CCC(CC=C)CC=C XURABDHWIADCPO-UHFFFAOYSA-N 0.000 description 1
- BXAVKNRWVKUTLY-UHFFFAOYSA-N 4-sulfanylphenol Chemical class OC1=CC=C(S)C=C1 BXAVKNRWVKUTLY-UHFFFAOYSA-N 0.000 description 1
- KAUQJMHLAFIZDU-UHFFFAOYSA-N 6-Hydroxy-2-naphthoic acid Chemical compound C1=C(O)C=CC2=CC(C(=O)O)=CC=C21 KAUQJMHLAFIZDU-UHFFFAOYSA-N 0.000 description 1
- KJKQQOHAWQQUDD-UHFFFAOYSA-N 6-hydroxynaphthalene-2-carboxylic acid;zinc Chemical compound [Zn].C1=C(O)C=CC2=CC(C(=O)O)=CC=C21 KJKQQOHAWQQUDD-UHFFFAOYSA-N 0.000 description 1
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- MOZDKDIOPSPTBH-UHFFFAOYSA-N Benzyl parahydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OCC1=CC=CC=C1 MOZDKDIOPSPTBH-UHFFFAOYSA-N 0.000 description 1
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 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
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- OUXHZAJDCBMTNQ-UHFFFAOYSA-N bis(4-hydroxy-3-methylphenyl) sulfite Chemical compound C1=C(O)C(C)=CC(OS(=O)OC=2C=C(C)C(O)=CC=2)=C1 OUXHZAJDCBMTNQ-UHFFFAOYSA-N 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 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 1
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 1
- 229940043351 ethyl-p-hydroxybenzoate Drugs 0.000 description 1
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000005165 hydroxybenzoic acids Chemical class 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- QTWZICCBKBYHDM-UHFFFAOYSA-N leucomethylene blue Chemical compound C1=C(N(C)C)C=C2SC3=CC(N(C)C)=CC=C3NC2=C1 QTWZICCBKBYHDM-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- GKFFBAQBFJBIDR-UHFFFAOYSA-N methyl 2,2-bis(4-hydroxyphenyl)acetate Chemical compound C=1C=C(O)C=CC=1C(C(=O)OC)C1=CC=C(O)C=C1 GKFFBAQBFJBIDR-UHFFFAOYSA-N 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
- 239000000203 mixture Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- RIKCMEDSBFQFAL-UHFFFAOYSA-N octyl 4-hydroxybenzoate Chemical compound CCCCCCCCOC(=O)C1=CC=C(O)C=C1 RIKCMEDSBFQFAL-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012766 organic filler Substances 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
- 238000011056 performance test Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 229960000790 thymol Drugs 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
- 230000002747 voluntary effect Effects 0.000 description 1
- 239000003232 water-soluble binding agent Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Heat Sensitive Colour Forming Recording (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
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、高感度で、耐光性、耐湿性に優れ感熱特性を改良
した感熱記録材料に関するものであり、特に発色感度及
び耐熱性を改良した感熱記録紙に関するものである。Detailed Description of the Invention (Field of Industrial Application) The present invention relates to a heat-sensitive recording material, and more particularly to a heat-sensitive recording material that is highly sensitive, has excellent light resistance and moisture resistance, and has improved heat-sensitive characteristics. In particular, it relates to a heat-sensitive recording paper with improved color development sensitivity and heat resistance.
（従来の技術）
感熱記録紙の記録層として具備すべき性能は耐自己発色
性、耐圧力発色性、耐光性、ｉｌ熱消色性、消色性、お
よびｉＪ水性などの感熱特性に優れていることであるが
、現在これらを完全に満足するものは得られていない。(Prior art) The recording layer of thermosensitive recording paper should have excellent heat-sensitive properties such as self-coloring resistance, pressure coloring resistance, light fastness, il thermal decolorizing property, decolorizing property, and iJ aqueous property. However, at present we have not found anything that completely satisfies these requirements.
一方、社会の要請による記録の高速伝送化に伴い、記録
装置自体の高速化は勿論であるがこれに対応し得る高感
度、即ち低エネルギーで濃度高く発色する感熱記録材料
が要求されている。On the other hand, as society demands higher speed recording transmission, there is a need not only for the speed of the recording apparatus itself to increase, but also for heat-sensitive recording materials with high sensitivity, that is, low energy and high density color development.
従来、発色感度を向上させるため、特開昭５７−１１６
６９０、特開昭５７−６４５９２ 、特開昭５８−１１
２７８８、特公昭５９−３０５５７、特開昭６０−５６
５８８、特開昭６０−８２３８２、特開昭６１−２７２
１８９、特開昭６３−１２６７８４、および特開昭６４
−４０３７３号公報などに、各種の化合物を感熱記録層
中に加える提案がある。Conventionally, in order to improve color development sensitivity, Japanese Patent Application Laid-Open No. 57-116
690, JP-A-57-64592, JP-A-58-11
2788, JP 59-30557, JP 60-56
588, JP-A-60-82382, JP-A-61-272
189, JP-A-63-126784, and JP-A-64
There are proposals to add various compounds to the heat-sensitive recording layer, such as in Japanese Patent No. 40373.
（発明が解決しようとする問題点）
本発明者らは、既知の電子供与性無色染料を発色剤とし
て用いて、従来公知の方法および上記した各特許公報に
記載されている方法に従い、感熱記録紙を製造し、感熱
記録紙として具備すべき性能について試験したところ、
発色感度が優れ、がっ、画像の安定性に優れた化合物は
地肌カブリおよび画像保存性試験後の地肌カブリが大き
く、感熱記録材料の高感度化の目的には不十分なもので
あった。(Problems to be Solved by the Invention) The present inventors used a known electron-donating colorless dye as a coloring agent to produce a thermosensitive recording medium according to a conventionally known method and the method described in each of the above-mentioned patent publications. When paper was manufactured and tested for the performance it should have as a thermal recording paper,
Compounds with excellent color development sensitivity and excellent image stability exhibited large background fog and background fog after image storage stability tests, and were unsatisfactory for the purpose of increasing the sensitivity of heat-sensitive recording materials.
（問題点を解決するための手段）
本発明者らは、既知の電子供与性無色染料を用いた感熱
記録材料について、上記の欠点を改良すべく鋭意研究し
た結果、本発明を完成したものであり、画像保存性試験
後の地肌を汚すことなく発色感度、及び耐熱性を改良し
た感熱記録紙を提供するものである。(Means for Solving the Problems) The present inventors have completed the present invention as a result of intensive research to improve the above-mentioned drawbacks of heat-sensitive recording materials using known electron-donating colorless dyes. The present invention provides a heat-sensitive recording paper that has improved color development sensitivity and heat resistance without staining the background after an image preservation test.
すなわち本発明は、
無色またはやや淡色を帯びた電子供与性無色染料と該電
子供与性無色染料を熱時発色させる酸性物質と結着剤と
を基本的に有する記録層を支持体上に設けてなる感熱記
録紙において、前記記録層中に一般式
（式中Ｒ１，Ｒｚは、低級アルキル基、置換されていて
もよい低級アルキル基、アルコキシ基、アラルキル基、
置換されていてもよいアラルキル基、ｎは、１から３の
整数。）で表される置換ベンゼン化合物を含有すること
を特徴とした感熱記録材料である。That is, the present invention provides a recording layer on a support that basically includes a colorless or slightly pale colorless electron-donating dye, an acidic substance that causes the colorless electron-donating dye to develop color when heated, and a binder. In the thermal recording paper, the recording layer contains a compound having the general formula (wherein R1 and Rz are a lower alkyl group, an optionally substituted lower alkyl group, an alkoxy group, an aralkyl group,
an optionally substituted aralkyl group, n is an integer from 1 to 3; ) is a heat-sensitive recording material characterized by containing a substituted benzene compound represented by:
本発明で用いる一般式（１）で表される化合物は、融点
を調節することで任意の感度の感熱記録材料を提供する
ことができるが、保存安定性と感度の面か゛ら融点４０
°Ｃから１５０°Ｃのものが好ましく、特に６０°Ｃか
ら１２０°Ｃのものが好ましい。The compound represented by the general formula (1) used in the present invention can provide a heat-sensitive recording material with any sensitivity by adjusting the melting point, but from the viewpoint of storage stability and sensitivity, the melting point is 40
A temperature of 150°C to 150°C is preferred, and a temperature of 60°C to 120°C is particularly preferred.
次頁に本発明の一般式（１）で表される化合物の具体例
を示すが本発明はこれらに限定されるものではない。Specific examples of the compound represented by the general formula (1) of the present invention are shown on the next page, but the present invention is not limited thereto.
本発明に使用する電子供与性無色染料としては、トリア
リルメタン系化合物、ジフェニルメタン系化合物、キサ
ンチン系化合物、チアジン系化合物、オキサジン系化合
物、スピロピラン系化合物、フルオレン系化合物などが
知られている。Known electron-donating colorless dyes used in the present invention include triallylmethane compounds, diphenylmethane compounds, xanthine compounds, thiazine compounds, oxazine compounds, spiropyran compounds, and fluorene compounds.
これらの一部を例示すれば、トリアリルメタン系化合物
として、３，３−ビス（Ｐ−ジメチルアミノフェニル）
−６−シフチルアミノフタリド（ＣＶＩ、ｌ、３．３−
ビス（Ｐ−ジメチルアミノフェニルフタリド）、１−（
Ｐ−ジメチルアミノフェニル１３−（１，３−ジメチル
インドール−３−イル）フタリド、３−（Ｐ−ジメチル
アミノフェニル） −３−（２−メチルインドール−３
−イル）フタリド、３，３−ビス（（２−（４−メトキ
シフェニル）−２−（４−ジメチルアミノフェニル）エ
チニル） ） −４，５，６，７テトラクロロフタリド
、３．３−ビス（（Ｌ １−ビス（４−ピロリジロノフ
ェニル）エチレン−２−イル） ） −１１，５，６，
７テトラクロロフタリド等があり、キザンテン化合物と
しては、ローダミンＢ−アニリノラクタム、ローダミン
Ｂ（Ｐ−ニトロアニリノ）ラクタム、ローダミンＢ（Ｐ
−クロロアニリノ）ラクタム、２−ジベンジルアミノ−
６−ジエチルアミノフルオラン、２−アニリノ−６−ジ
エチルアミノフルオラン、２−アニリノ−３−メチル−
６−ジエチルアミノフルオラン、２−アニリノ−３−メ
チル−６−（Ｎ−シクロへキシル−Ｎ−メチル）アミノ
フルオラン、２−ｏ−クロロアニリノ−６−ジエチルア
ミノフルオラン、２−０−クロロアニリノ−６−ジブチ
ルアミノフルオラン、２−ｐ−クロロアニリノ−６−ジ
エチルアミノフルオラン、２−オクチルアミノ−６−ジ
エチルアミノフルオラン、２−Ｔ）−アセチルアニリノ
−６−ジエチルアミノフルオラン、２−エトキシエチル
アミノ−３−クロロ−６−ジエチルアミノフルオラン、
２−アニリノ−３−クロロ−６−ジエチルアミノフルオ
ラン、２−ジフェニルアミノ−６−ジエチルアミノフル
オラン、２−アニリノ−６−（Ｎ−エチル−Ｎ−）リル
）アミノフルオラン、２−アニリノ−３−メチル−６−
（Ｎ−エチル−１１−１−リル）アミノフルオラン、２
−アニリノ−３−メチル−６−（Ｎ−メチル−Ｎ−ｎ−
プロピル）アミノフルオラン、２−アニリノ−３−メト
キシ−６−ジブチルアミノフルオラン、２−アニリノ−
３−メチル−６−Ｎ、Ｎ−ジブチルアミノフルオラン、
２−アニリノ−３−メチル−６−（Ｎ−エチル−Ｎ−テ
トラヒドロフルフリル）アミノフルオラン、２−アニリ
ノ−３−メチル−６−（Ｎ−ｎ−ブチル−Ｎ−テトラヒ
ドロフルフリル）アミノフルオラン、２−アニリノ−３
−メチル−６−（Ｎ−エチル−Ｎ−イソアミル）アミノ
フルオラン、２−り四ロー３−メチル−６−ｐ−（ｐ−
フェニルアミノフェニル）アミノアニリノフルオラン、
２−ｐ−フェニルウレイドアニリノ−６−Ｎ−シクロヘ
キシル−Ｎ−メチルアミノフルオラン等があり、フルオ
レン系化合物としては、３’、 ６ ’ビスジエチルア
ミノー５−ジエチルアミノスピロ（イソヘンシフラン−
１，９−フルオレン）−３’−オン、３’、 ６ ’ビ
スジエチルアミノー５−ジブチルアミノスピロ（イソヘ
ンシフラン−１，９−フル第レン）−３′−オン等があ
り、ペンタジェン系化合物としては、１−（α−メトキ
シ（４−Ｎ、Ｎ−ジメチルアミノ）ベンジル）−３−（
４−Ｎ、Ｎ−ジメチルアミノベンジリデン）−５−メチ
ル−シクロヘキセン等があり、チアジン系化合物として
は、ペンゾイルリューコメチレンブルー、ｐ−ニトロベ
ンジルリューコメチレンブルー等があり、オキサジン系
化合物としては、３．７−ビス（ジエチルアミノ）−１
０−ベンゾイル−フェノキサジン、３．７−ビス（ジエ
チルアミノ）−１０−アセチルフェノキサジン等があり
、スピロ系化合物としては、３−メチルスピロ−ジナフ
トピラン、３−ベンジルスピロ−ジナフトピラン、３−
プロピルスピロ−ジベンゾビラン等がある。Some examples of these include 3,3-bis(P-dimethylaminophenyl) as a triallylmethane compound.
-6-Cyphtylaminophthalide (CVI, l, 3.3-
Bis(P-dimethylaminophenyl phthalide), 1-(
P-dimethylaminophenyl 13-(1,3-dimethylindol-3-yl)phthalide, 3-(P-dimethylaminophenyl)-3-(2-methylindole-3
-yl)phthalide, 3,3-bis((2-(4-methoxyphenyl)-2-(4-dimethylaminophenyl)ethynyl)) -4,5,6,7tetrachlorophthalide, 3.3- Bis((L 1-bis(4-pyrrolidylonophenyl)ethylene-2-yl) ) -11,5,6,
7 tetrachlorophthalide, etc., and xanthene compounds include rhodamine B-anilinolactam, rhodamine B (P-nitroanilino)lactam, rhodamine B (P
-chloroanilino)lactam, 2-dibenzylamino-
6-diethylaminofluorane, 2-anilino-6-diethylaminofluorane, 2-anilino-3-methyl-
6-diethylaminofluorane, 2-anilino-3-methyl-6-(N-cyclohexyl-N-methyl)aminofluorane, 2-o-chloroanilino-6-diethylaminofluorane, 2-0-chloroanilino-6 -dibutylaminofluorane, 2-p-chloroanilino-6-diethylaminofluorane, 2-octylamino-6-diethylaminofluorane, 2-T)-acetylanilino-6-diethylaminofluorane, 2-ethoxyethylamino- 3-chloro-6-diethylaminofluorane,
2-anilino-3-chloro-6-diethylaminofluorane, 2-diphenylamino-6-diethylaminofluorane, 2-anilino-6-(N-ethyl-N-)lyl)aminofluorane, 2-anilino-3 -methyl-6-
(N-ethyl-11-1-lyl)aminofluorane, 2
-anilino-3-methyl-6-(N-methyl-N-n-
propyl)aminofluorane, 2-anilino-3-methoxy-6-dibutylaminofluorane, 2-anilino-
3-methyl-6-N,N-dibutylaminofluorane,
2-anilino-3-methyl-6-(N-ethyl-N-tetrahydrofurfuryl)aminofluorane, 2-anilino-3-methyl-6-(N-n-butyl-N-tetrahydrofurfuryl)aminofluoran Oran, 2-anilino-3
-Methyl-6-(N-ethyl-N-isoamyl)aminofluorane, 2-di-4-3-methyl-6-p-(p-
phenylaminophenyl) aminoanilinofluorane,
Examples of fluorene compounds include 2-p-phenylureidoanilino-6-N-cyclohexyl-N-methylaminofluorane, and examples of fluorene compounds include 3',6'bisdiethylamino-5-diethylaminospiro(isohensifuran-
1,9-fluorene)-3'-one, 3',6'bisdiethylamino-5-dibutylaminospiro(isohensyfuran-1,9-fluorene)-3'-one, etc., and pentadiene compounds include , 1-(α-methoxy(4-N,N-dimethylamino)benzyl)-3-(
Examples of thiazine compounds include penzoyl leucomethylene blue and p-nitrobenzyl leucomethylene blue, and oxazine compounds include 3.7- Bis(diethylamino)-1
There are 0-benzoyl-phenoxazine, 3,7-bis(diethylamino)-10-acetylphenoxazine, etc., and spiro-based compounds include 3-methylspiro-dinaphthopyran, 3-benzylspiro-dinaphthopyran, 3-
Examples include propyl spiro-dibenzobilane.
これらは、単独または、混合して用いられる。These may be used alone or in combination.
本発明は、これら電子供与性無色染料に限定されるもの
ではない。The present invention is not limited to these electron-donating colorless dyes.
本発明に用いられる電子受容性化合物（顕色剤）として
は、フェノール系化合物、有機酸あるいはその金属塩、
ヒドロキシ安息香酸エステル等が好ましく、具体的には
次のようなものがあげられる。Examples of the electron-accepting compound (developer) used in the present invention include phenolic compounds, organic acids or metal salts thereof,
Hydroxybenzoic acid esters are preferred, and specific examples include the following.
サルチル酸、３−イソプロピルサリチル酸、３゜５−ジ
ーｔｅｒ、−ブチルサリチル酸、３．５−ジ−α−メチ
ルベンジルサリチル酸、４．４′−イソプロビリ′デン
ジフェノール、４．４’−イソプロピリデンビス（２−
クロロフェノール）、４．４’−イソプロピリデンビス
（２，６−ジクロロフェノール） 、４．４’−イソプ
ロピリデンビス（２，６−シフチルフエノール）、４．
４’−イソプロピリデンビス（２−ｔｅｒ。Salicylic acid, 3-isopropylsalicylic acid, 3゜5-di-ter,-butylsalicylic acid, 3.5-di-α-methylbenzylsalicylic acid, 4.4'-isopropylidene diphenol, 4.4'-isopropylidene bis( 2-
chlorophenol), 4.4'-isopropylidene bis(2,6-dichlorophenol), 4.4'-isopropylidene bis(2,6-cyphthylphenol), 4.
4'-isopropylidene bis(2-ter.
−ブチルフェノール） 、４．４’−シクロへキシリデ
ンビスフェノール、４．４’−シクロへキシリデンビス
（２−メチルフェノール）、４−ｔｅ乙−ブチルフェノ
ール、４−フェニルフェノール、４−ヒドロキシジフェ
ノキシド、α−ナフトール、β−ナフトール、３Ｉ５−
キシレノール、チモール、メチル−ビス（４−ヒドロキ
シフェニル）アセテート、ｎ−ブチル−ビス（４−ヒド
ロキシフェニル）アセテート、４．４′−チオジフェノ
ール、ビス（４−ヒドロキシ−３−メチルフェニル）ス
ルフイツト、４．４′−ジフェノールスルホン、４−イ
ソプロホキシー４′−ヒドロキシジフェニルスルホン、
１．７−ジ（４−ヒドロキシフェニルチオ）−３，５−
ジオキサへブタン、フロログリシンカルボン酸、４−ｔ
ｅｒ、−オクチルカテコール、２．２’−メチレンビス
（４−クロロフェノールＬ２，２’−メチレンビス（４
−メチル−６ｔｅｒ、−ブチルフェノール）、２．２′
−ジヒドロキシジフェニル、ｐ−ヒドロキシ安息香酸エ
チル、Ｐ−ヒドロキシ安息香酸プロピル、ｐ−ヒドロキ
シ安息香酸ブチル、Ｐ−ヒドロキシ安息香酸ベンジル、
ｐ−ヒドロキシ安息香酸−ｐ−クロロベンジル、ｐ−ヒ
ドロキシ安息香酸−〇−クロロベンジル、ｐ−ヒドロキ
シ安息香酸−ｐ−メチルベンジル、ｐ−ヒドロキシ安息
香酸−ｎ−オクチル、安息香酸、サリチル酸亜鉛、１−
ヒドロキシ−２−ナフトエ酸、２−ヒドロキシ−６−ナ
フトエ酸、２−ヒドロキシ−６−ナフトエ酸亜鉛、４−
ヒドロキシジフェニルスルホン、４−ヒドロキシ−４′
−クロロジフェニルスルホン、２−ヒドロキシ−ｐ−ト
ルイル酸、３．５−ｔｅｒ、 −ブチルサリチル酸亜鉛
、３．５− ｔｅｒ、−プチルサリチル酸銀、酒石酸、
しゅろ酸、マレイン酸、クエン酸、コハク酸、ステアリ
ン酸、４−ヒドロキシエチル酸、はう酸、チオ尿素誘導
体、４−ヒドロキシチオフェノール誘導体等がある。-butylphenol), 4.4'-cyclohexylidenebisphenol, 4.4'-cyclohexylidenebis(2-methylphenol), 4-te-butylphenol, 4-phenylphenol, 4-hydroxydiphenoxide, α- naphthol, β-naphthol, 3I5-
Xylenol, thymol, methyl-bis(4-hydroxyphenyl) acetate, n-butyl-bis(4-hydroxyphenyl) acetate, 4,4'-thiodiphenol, bis(4-hydroxy-3-methylphenyl) sulfite, 4.4'-diphenolsulfone, 4-isoprofoxy 4'-hydroxydiphenylsulfone,
1,7-di(4-hydroxyphenylthio)-3,5-
Dioxahebutane, phloroglycin carboxylic acid, 4-t
er, -octylcatechol, 2,2'-methylenebis(4-chlorophenol L2,2'-methylenebis(4
-methyl-6ter, -butylphenol), 2.2'
-dihydroxydiphenyl, ethyl p-hydroxybenzoate, propyl p-hydroxybenzoate, butyl p-hydroxybenzoate, benzyl p-hydroxybenzoate,
p-chlorobenzyl p-hydroxybenzoate, 〇-chlorobenzyl p-hydroxybenzoate, p-methylbenzyl p-hydroxybenzoate, n-octyl p-hydroxybenzoate, benzoic acid, zinc salicylate, 1 −
Hydroxy-2-naphthoic acid, 2-hydroxy-6-naphthoic acid, zinc 2-hydroxy-6-naphthoic acid, 4-
Hydroxydiphenylsulfone, 4-hydroxy-4'
-chlorodiphenylsulfone, 2-hydroxy-p-toluic acid, 3.5-ter, -zinc butylsalicylate, 3.5-ter, -silver butylsalicylate, tartaric acid,
Examples include oxalic acid, maleic acid, citric acid, succinic acid, stearic acid, 4-hydroxyethylic acid, oxalic acid, thiourea derivatives, and 4-hydroxythiophenol derivatives.
発色剤と顕色剤との混合物を支持体シート上に結着させ
る結着剤としては水溶性または非水溶性の結着剤を用い
る。代表的なものとしてはポリビニルアルコール、メチ
ルセルローズ、ヒドロキシエチルセルローズ、カルボキ
シメチルセルローズ、アラビアゴム、でん粉、ゼラチン
、カゼイン、ポリビニルピロリドン、スチレン−無水マ
レイン酸共重合物、ポリアクリル酸アミド、ポリアクリ
ル酸塩、テルペン樹脂および石油樹脂等があるが、本発
明で特に好適に使用しうる結着剤は水溶性結着剤であり
、その代表的なものはポリビニルアルコールである。A water-soluble or water-insoluble binder is used as the binder for binding the mixture of color former and color developer onto the support sheet. Typical examples include polyvinyl alcohol, methyl cellulose, hydroxyethyl cellulose, carboxymethyl cellulose, gum arabic, starch, gelatin, casein, polyvinylpyrrolidone, styrene-maleic anhydride copolymer, polyacrylic acid amide, and polyacrylate. , terpene resins, petroleum resins, etc., but the binder that can be particularly preferably used in the present invention is a water-soluble binder, and a typical example thereof is polyvinyl alcohol.
次に本発明の感熱記録材料を用いた感熱記録紙の具体的
な製造例を示す。Next, a specific example of manufacturing a heat-sensitive recording paper using the heat-sensitive recording material of the present invention will be shown.
感熱記録紙を製造する際に記録層中における上記した各
成分および結着剤のそれぞれの重量比は、発色剤に対し
本発明化合物の一般式（１）で表される化合物の総量は
０，５〜１０倍、好ましくは１〜４倍であり、結着剤は
０．３〜３倍、好ましくは０．５〜２倍である。発色剤
および顕色剤は、好ましくはそれぞれ別々にボールミル
、ダイノーミル、サンドミルまたはペイントコンディシ
ョナーなどの分散機を用いて分散し、また、本発明にか
かわる一般式（１）で表される化合物は単独、または発
色剤と共に、または顕色剤と共に分１１ダシてもよく、
結着剤を含有する水あるいは有機媒体中で、好ましくは
結着剤が溶解している水を媒体として分散し、粉砕して
１〜６μ、好まし、くは１〜３μの粒径とした懸濁液を
つくる。必要ならば消泡剤、分散剤または増白剤などを
加えて分散し、粒砕してもよい。When producing heat-sensitive recording paper, the weight ratio of each of the above-mentioned components and binder in the recording layer is such that the total amount of the compound represented by the general formula (1) of the compound of the present invention is 0, It is 5 to 10 times, preferably 1 to 4 times, and the binder is 0.3 to 3 times, preferably 0.5 to 2 times. The color forming agent and the color developer are preferably dispersed separately using a dispersing machine such as a ball mill, a dyno mill, a sand mill, or a paint conditioner, and the compound represented by the general formula (1) according to the present invention is dispersed alone, Alternatively, it may be mixed with a color former or a color developer,
Disperse in water or an organic medium containing a binder, preferably water in which the binder is dissolved, and pulverize to a particle size of 1 to 6 μm, preferably 1 to 3 μm. Make a suspension. If necessary, an antifoaming agent, dispersant, or brightener may be added for dispersion and pulverization.
次に上記したそれぞれを別々に分散し、粉砕した各成分
の懸濁液を記録層中における各成分の重量比が上記した
ように混合して熱感記録層を形成させるための塗料とす
る。この塗料を紙の表面にワイヤーバーＮ０．６〜Ｎｏ
、２０を用い、乾燥後の固形物の重量が３〜Ｌｏｇ／ｎ
（になるように塗布し、室温〜７０°Ｃの送風乾燥機中
で乾燥することにより感熱記録紙を製造する。必要に応
じ熱ヘットの対融着性、筆記性などを改善するために無
機または有機充填剤を塗料に加えてもよい。Next, each of the above-mentioned components is separately dispersed, and a suspension of the pulverized components is mixed so that the weight ratio of each component in the recording layer is as described above to prepare a paint for forming a heat-sensitive recording layer. Apply this paint to the surface of the paper with wire bar No. 0.6 to No.
, 20, and the weight of the solid after drying is 3 to Log/n.
(Thermal recording paper is manufactured by coating the paper so that Alternatively, organic fillers may be added to the paint.
（発明の効果）
このようにして得られた感熱記録紙は、感熱特性のうち
、特に発色感度が極めて優れており、さらには感熱記録
紙としての商品価値を損ねる白化現象もなく、耐熱性お
よび耐熱地肌のカブリも優れた、従来既知の感熱記録紙
の欠点を良く克服するものであった。(Effects of the Invention) The heat-sensitive recording paper thus obtained has excellent heat-sensitive properties, particularly color development sensitivity, and also has no whitening phenomenon that impairs its commercial value as a heat-sensitive recording paper, and has excellent heat resistance and It also has excellent heat-resistant background fog, which effectively overcomes the drawbacks of conventionally known heat-sensitive recording papers.
（実施例）
以下に本発明を実施例により具体的に説明するが、本発
明はこれらの実施例によって限定されるものではない。(Examples) The present invention will be specifically explained below using Examples, but the present invention is not limited by these Examples.
実施例 Ｉ
Ａ液（染料分散′ａ、）
２−アニリノ−３−メチ刀へ〇−
ジブチルアミノフルオラン ・・・・８ 部ステアリン
酸アマイド ・・・・・・４ 部１０％ポリビニルアル
コール
水溶液 ・・・・・・・・・・・・４０ 部水 ・
・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・
２８ 部Ｂ液（顕色剤分散液）
ＢＰＡ・・・・・・・・・・・・・５部ステアリン酸亜
鉛 ・・・・・・・・３ 部２．５−ジヘンジルーＰ−
キシレン
（化合物ａ、融点９５〜９７°Ｃ）・・・・６ 部４．
４′−ブチリデンビス−（３−メチル−５−ｔｅ乙−ブ
チル）フェノール ・・・１．５部１０％ポリビニルア
ルコール ・・１０ 部水 ・ ・ ・ ・ ・ ・
・ ・ ・ ・ ・ ・ ・ ・ ５４．５部Ｃ液（
フィラー分散液）
３０％カルシウムカーボ不−１・分散液り液（結着剤液
）
１０％ポリビニルアルコ−ル
上記組成物の各法、Ａ，ＢおよびＣをダイノーミルＫＤ
Ｌ分散機で粒径１．５〜３μまで粉砕する。Example I Solution A (dye dispersion 'a,) 2-anilino-3-methoxydibutylaminofluorane 8 parts Stearamide 4 parts 10% polyvinyl alcohol aqueous solution・・・・・・・・・・・・40 Part water ・
・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ ・
28 Part B liquid (color developer dispersion) BPA・・・・・・・・・・・・5 parts Zinc stearate・・・・・・3 Parts 2.5-Dihenjiru P-
Xylene (compound a, melting point 95-97°C)...6 parts 4.
4'-Butylidenebis-(3-methyl-5-te-butyl)phenol...1.5 parts 10% polyvinyl alcohol...10 parts Water...
・ ・ ・ ・ ・ ・ ・ ・ 54.5 parts of liquid C (
Filler dispersion) 30% calcium carbonate dispersion (binder liquid) 10% polyvinyl alcohol
Grind to a particle size of 1.5 to 3μ using an L disperser.
次に下記の割合で各法を混合して感熱塗料とする。Next, each method is mixed in the following proportions to prepare a heat-sensitive paint.
Ａ液 ・・・・・・・・・・・・・ ４ 部Ｂ液 ・・
・・・・・・・・・・・１６ 部Ｃン１（（・・・・・
・・・・・・・・１０部り液・・・・・・・・・・・・
・８部
この混合塗料を上質紙の表面にＮｏ． １ ８のワイヤ
ーバーを用い、乾燥後の固形分重量が７ｇ／ｆｆｌにな
るように塗布し、送風乾燥機中に入れ乾燥した。A liquid ・・・・・・・・・・・・・・・ 4 parts B liquid ・・・
・・・・・・・・・・・・16 Part C-1 ((・・・・・・
・・・・・・・・・10 parts liquid・・・・・・・・・・・・
・8 parts Apply this mixed paint to the surface of high-quality paper. Using a No. 18 wire bar, the coating was applied so that the solid content weight after drying was 7 g/ffl, and the coating was placed in a blow dryer to dry.
このようにして感熱記録紙を得た。A thermosensitive recording paper was thus obtained.
実施例 ２
実施例１中のＢ液中の２，５−ジベンジル−ｐ−キシレ
ンを２＋５−ジヘンジルヒドロキノンジエチルエーテル
（化合物ｂ、融点９４〜９６°Ｃ）に変えた他は、Ｂ液
作成と全く同じに行いＰ．液分散液を得た。Example 2 Prepare Solution B except that 2,5-dibenzyl-p-xylene in Solution B in Example 1 was changed to 2+5-dihenzylhydroquinone diethyl ether (compound b, melting point 94-96°C) Do exactly the same as P. A liquid dispersion was obtained.
次に下記の割合で各法を混合して感熱５料とする。Next, each method was mixed in the proportions shown below to prepare five heat-sensitive materials.
Ａン（（（・・・・・・・・・・・４部Ｈ液 ・・・・
・・・・・・・・・１６ 部Ｃ液 ・・・・・・・・・
・・・・１０ 部り液 ・・・・・・・・・・・・・
８ 部以下上記塗料を用い、実施例１と全く同様に行い
、感熱記録紙を得た。A (((......4 parts H solution...
・・・・・・・・・16 part C liquid ・・・・・・・・・
・・・・・・10 parts liquid ・・・・・・・・・・・・・・・
A thermosensitive recording paper was obtained in exactly the same manner as in Example 1 using 8 parts or less of the above paint.
実施例３
Ｂ液中の本発明化合物２，５−ジベンジル−ｐ−キシレ
ンを２．５−ジベンジルヒドロキノンジメチルエーテル
（化合物Ｃ１融点１０２〜１０３°Ｃ）に変えた他は、
Ｂ液作成と全く同じに行いＦ液分散液を得た。Example 3 The present compound 2,5-dibenzyl-p-xylene in solution B was changed to 2,5-dibenzylhydroquinone dimethyl ether (compound C1 melting point 102-103°C).
A dispersion of liquid F was obtained in exactly the same manner as in the preparation of liquid B.
次に下記の割合で各法を混合して感熱塗料とする。Next, each method is mixed in the following proportions to prepare a heat-sensitive paint.
Ａ液 ・・・・・・・・・・・・・ ４ 部Ｈ液 ・・
・・・・・・・・・・・１６ 部Ｃ液 ・・・・・・・
・・・・・・１０ 部り液 ・・・・・・・・・・・・
・ ８ 部以下上記塗料を用い、実施例１と全く同様に
行い、感熱記録紙を得た。A liquid ・・・・・・・・・・・・ 4 parts H liquid ・・・
・・・・・・・・・・・・16 part C liquid ・・・・・・・
・・・・・・10 parts liquid ・・・・・・・・・・・・
- Using 8 parts or less of the above coating material, the same procedure as in Example 1 was carried out to obtain thermal recording paper.
対照例 １
Ｂ液中の本発明化合物２．５−ジベンジル−Ｐ−キシレ
ンを４−ベンジルビフェニルに変えた他は、Ｂ液作成と
全く同じに行いＧ液分散液を得た。Control Example 1 A dispersion of liquid G was obtained in exactly the same manner as in the preparation of liquid B, except that 2.5-dibenzyl-P-xylene of the present invention compound in liquid B was changed to 4-benzylbiphenyl.
次に下記の割合で各法を混合して感熱塗料とする。Next, each method is mixed in the following proportions to prepare a heat-sensitive paint.
Ａ液 ・・・・・・・・・・・・・ ４ 部Ｇ液 ・・
・・・・・・・・・・・１６ 部Ｃ液 ・・・・・・・
・・・・・・１０ 部り液 ・・・・・・・・・・・・
・ ８ 部以下上記塗料を用い、実施例１と全く同様に
行い、感熱記録紙を得た。A liquid ・・・・・・・・・・・・・・・ 4 parts G liquid ・・・
・・・・・・・・・・・・16 part C liquid ・・・・・・・
・・・・・・10 parts liquid ・・・・・・・・・・・・
- Using 8 parts or less of the above coating material, the same procedure as in Example 1 was carried out to obtain thermal recording paper.
対照例 ２
Ｂ液中の本発明化合物２．５−ジベンジル−Ｐ−キシレ
ンを２−ベンジルオキシナフタレンに変えた他は、Ｂ液
作成と全く同じに行いＨ液分散液を得た。Control Example 2 A dispersion of liquid H was obtained in exactly the same manner as in the preparation of liquid B, except that the compound of the present invention, 2.5-dibenzyl-P-xylene in liquid B, was changed to 2-benzyloxynaphthalene.
次に下記の割合で各法を混合して感熱塗料とする。Next, each method is mixed in the following proportions to prepare a heat-sensitive paint.
Ａ液 ・・・・・・・・・・・・・ ４ 部Ｈ液 ・・
・・・・・・・・・・・１６ 部Ｃ液 ・・・・・・・
・・・・・・１０ 部り液 ・・・・・・・・・・・
・・ ８ 部以下上記塗料を用い、実施例１と全く同様
に行い、感熱記録紙を得た。A liquid ・・・・・・・・・・・・ 4 parts H liquid ・・・
・・・・・・・・・・・・16 part C liquid ・・・・・・・
・・・・・・10 parts liquid ・・・・・・・・・・・・
... 8 parts or less of the above paint was carried out in exactly the same manner as in Example 1 to obtain thermal recording paper.
実施例１、実施例２、実施例３及び対照例１、対照例２
で得られた感熱記録紙について、それぞれ２０ｃｍ幅の
所定用紙にカットして、ユリロール製ミニカレンダーで
平滑度が３００秒になるようにカレンダー処理を行い、
性能試験を行った。Example 1, Example 2, Example 3 and Comparative Example 1, Comparative Example 2
The thermal recording paper obtained in step 1 was cut into 20 cm wide sheets and calendered using a mini calender manufactured by Yuriroll to achieve a smoothness of 300 seconds.
A performance test was conducted.
結果を表−１中の実施例および表−２中の対照例の欄に
示す。The results are shown in the Examples column in Table 1 and the Control Example column in Table 2.
表−１
表−２
注−１＝発色濃度を縦軸に、発色エネルギーを横軸にグ
ラフ化した発色濃度−発色エネルギー曲線において、松
下電子部品■製、動的発色試験機条件で感熱記録紙を発
色させた。発色部分をマクベス反射濃度計ＲＤ−９１８
で測定し、反射濃度１．０を示す発色エネルギーをＪｌ
、０とし、このときのエネルギー（ｍｊ／闘２）を発色
感度と名称した。Table-1 Table-2 Note-1 = Color density-color energy curve graphed with color density on the vertical axis and color energy on the horizontal axis. colored. Macbeth reflection densitometer RD-918 for colored part
The coloring energy that shows a reflection density of 1.0 is Jl.
, 0, and the energy (mj/to2) at this time was named color development sensitivity.
注−２：上記性−１の条件下の未発色部分を地肌ＤＯと
した。Note-2: The uncolored area under the conditions of property-1 above was defined as background DO.
注−３：印字発色後の耐熱保存性を表し、上記性−１の
条件で発色したＪ １．０の部分を６０’Ｃ，２４時間
後の発色濃度Ｄ２を測定し、発色残存率−（Ｄ２／１．
０） Ｘ １００を求め、これを耐熱性とした。Note-3: Indicates the heat-resistant storage stability after printing color development, and the color development density D2 was measured after 24 hours at 60'C for the J 1.0 part that was colored under the conditions of property-1 above, and the color retention rate - ( D2/1.
0) X 100 was determined, and this was defined as heat resistance.
注−４二上記法−３の未発色部分を６０゛Ｃ１２４時間
後の発色濃度を測定し、これを耐熱地肌Ｄ３と名称した
。Note 4 2 The color density of the uncolored portion obtained in the above method 3 was measured after 124 hours at 60°C, and this was designated as heat-resistant skin D3.
本発明の感熱記録材料は表１及び表２から明かなよ・う
に従来公知の増感剤を含有した感熱記録紙と比較し、地
肌カブリが白く良好で、発色感度および耐熱保存性の向
上が著しい、感熱記録紙として優れた性能が得られた。As is clear from Tables 1 and 2, the heat-sensitive recording material of the present invention has whiter background fog and improved color development sensitivity and heat-resistant storage stability compared to heat-sensitive recording paper containing conventionally known sensitizers. Remarkably excellent performance as a thermal recording paper was obtained.
保土谷化学工業株式会社 手続補正書（自発） 平成２年１２月１７目Hodogaya Chemical Industry Co., Ltd. Procedural amendment (voluntary) December 17th, 1990
Claims (1)
子供与性無色染料を熱時発色させる酸性物質と結着剤と
を基本的に有する記録層を支持体上に設けてなる感熱記
録紙において、前記記録層中に一般式 ▲数式、化学式、表等があります▼（１） （式中Ｒ＿１、Ｒ＿２は、低級アルキル基、置換されて
いてもよい低級アルキル基、アルコキシ基、アラルキル
基、置換されていてもよいアラルキル基、ｎは、１から
３の整数。）で表される置換ベンゼン化合物を含有する
ことを特徴とした感熱記録材料。[Claims] A recording layer is provided on a support, which basically includes a colorless or slightly pale colorless electron-donating dye, an acidic substance that causes the colorless electron-donating dye to develop color when heated, and a binder. In the thermal recording paper made of 1. A heat-sensitive recording material, comprising a substituted benzene compound represented by a group, an aralkyl group, an optionally substituted aralkyl group, n is an integer from 1 to 3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2279310A JPH04156381A (en) | 1990-10-19 | 1990-10-19 | Thermally sensitive material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2279310A JPH04156381A (en) | 1990-10-19 | 1990-10-19 | Thermally sensitive material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04156381A true JPH04156381A (en) | 1992-05-28 |
Family
ID=17609385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2279310A Pending JPH04156381A (en) | 1990-10-19 | 1990-10-19 | Thermally sensitive material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04156381A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7865420B1 (en) | 2001-01-22 | 2011-01-04 | Voyager Technologies, Inc. | Real time electronic commerce telecommunication system and method |
-
1990
- 1990-10-19 JP JP2279310A patent/JPH04156381A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7865420B1 (en) | 2001-01-22 | 2011-01-04 | Voyager Technologies, Inc. | Real time electronic commerce telecommunication system and method |
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