JPH0316781A - Material for thermal recording - Google Patents
Material for thermal recordingInfo
- Publication number
- JPH0316781A JPH0316781A JP1151304A JP15130489A JPH0316781A JP H0316781 A JPH0316781 A JP H0316781A JP 1151304 A JP1151304 A JP 1151304A JP 15130489 A JP15130489 A JP 15130489A JP H0316781 A JPH0316781 A JP H0316781A
- Authority
- JP
- Japan
- Prior art keywords
- group
- acid
- compound
- electron
- color
- 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 43
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 239000003086 colorant Substances 0.000 claims abstract description 14
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 10
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 8
- 238000002844 melting Methods 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid group Chemical group C(C(=O)O)(=O)O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N fumaric acid group Chemical group C(\C=C\C(=O)O)(=O)O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 5
- 238000010030 laminating Methods 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 230000001568 sexual effect Effects 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 abstract description 10
- 239000000725 suspension Substances 0.000 abstract description 10
- 238000004040 coloring Methods 0.000 abstract description 4
- 230000008018 melting Effects 0.000 abstract description 3
- 238000006467 substitution reaction Methods 0.000 abstract 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- KIWSYRHAAPLJFJ-DNZSEPECSA-N n-[(e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enyl]pyridine-3-carboxamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/CNC(=O)C1=CC=CN=C1 KIWSYRHAAPLJFJ-DNZSEPECSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 description 43
- 238000000576 coating method Methods 0.000 description 42
- -1 Lactone compounds Chemical class 0.000 description 41
- 239000011248 coating agent Substances 0.000 description 37
- 239000002253 acid Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 12
- 150000002989 phenols Chemical class 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- 150000001991 dicarboxylic acids Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910000019 calcium carbonate Inorganic materials 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 150000004780 naphthols Chemical class 0.000 description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 3
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000011230 binding agent Substances 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 3
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 239000000843 powder Substances 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
- 239000008117 stearic acid Substances 0.000 description 3
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 2
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 2
- WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- XJMMNTGIMDZPMU-UHFFFAOYSA-N 3-methylglutaric acid Chemical compound OC(=O)CC(C)CC(O)=O XJMMNTGIMDZPMU-UHFFFAOYSA-N 0.000 description 2
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
- NPFYZDNDJHZQKY-UHFFFAOYSA-N 4-Hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 NPFYZDNDJHZQKY-UHFFFAOYSA-N 0.000 description 2
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- TXXHDPDFNKHHGW-CCAGOZQPSA-N Muconic acid Natural products OC(=O)\C=C/C=C\C(O)=O TXXHDPDFNKHHGW-CCAGOZQPSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 150000001408 amides Chemical class 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
- 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
- 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 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- TXXHDPDFNKHHGW-UHFFFAOYSA-N muconic acid Chemical compound OC(=O)C=CC=CC(O)=O TXXHDPDFNKHHGW-UHFFFAOYSA-N 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 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
- 150000003839 salts Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000010998 test method Methods 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
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- KDUWXMIHHIVXER-UHFFFAOYSA-N 2'-hydroxypropiophenone Chemical compound CCC(=O)C1=CC=CC=C1O KDUWXMIHHIVXER-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- UWEZBKLLMKVIPI-UHFFFAOYSA-N 2,5-dinitrophenol Chemical compound OC1=CC([N+]([O-])=O)=CC=C1[N+]([O-])=O UWEZBKLLMKVIPI-UHFFFAOYSA-N 0.000 description 1
- JCRIDWXIBSEOEG-UHFFFAOYSA-N 2,6-dinitrophenol Chemical compound OC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O JCRIDWXIBSEOEG-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- QKJAZPHKNWSXDF-UHFFFAOYSA-N 2-bromoquinoline Chemical compound C1=CC=CC2=NC(Br)=CC=C21 QKJAZPHKNWSXDF-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- BCKXMQIYWWTZDP-UHFFFAOYSA-N 2-hydroxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1O BCKXMQIYWWTZDP-UHFFFAOYSA-N 0.000 description 1
- FQEORPZFSMZRSP-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonitrile Chemical compound C1=CC=CC2=C(C#N)C(O)=CC=C21 FQEORPZFSMZRSP-UHFFFAOYSA-N 0.000 description 1
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- QVIKUAVXSRNDPS-UHFFFAOYSA-N 2-methoxynaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(OC)=CC=C21 QVIKUAVXSRNDPS-UHFFFAOYSA-N 0.000 description 1
- AQYCMVICBNBXNA-UHFFFAOYSA-N 2-methylglutaric acid Chemical compound OC(=O)C(C)CCC(O)=O AQYCMVICBNBXNA-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
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- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UHDKXFCUGVGVDP-UHFFFAOYSA-N n-ethyl-2-hydroxybenzamide Chemical compound CCNC(=O)C1=CC=CC=C1O UHDKXFCUGVGVDP-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 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
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical class C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 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
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- ZNOZEKFDBJRBMI-UHFFFAOYSA-M sodium;4-(2-ethylhexoxy)-4-oxo-3-sulfobutanoate Chemical compound [Na+].CCCCC(CC)COC(=O)C(S(O)(=O)=O)CC([O-])=O ZNOZEKFDBJRBMI-UHFFFAOYSA-M 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229920006027 ternary co-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
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- JRBNKLYSGIHONX-UHFFFAOYSA-L zinc;1-carboxynaphthalen-2-olate Chemical compound [Zn+2].C1=CC=C2C(C(=O)O)=C([O-])C=CC2=C1.C1=CC=C2C(C(=O)O)=C([O-])C=CC2=C1 JRBNKLYSGIHONX-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Heat Sensitive Colour Forming Recording (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野コ
本発明は感熱記録用材料に関する。さらに詳しくは発色
感度が極めて高く、かつ白色度に優れる感熱記録用材料
に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a heat-sensitive recording material. More specifically, the present invention relates to a heat-sensitive recording material that has extremely high color development sensitivity and excellent whiteness.
［従来の技術コ
感熱．記録用材料は電子受容性顕色性物質（以下発色剤
ともいう）と電子受容性の顕色性物質（以下顕色剤と略
記する）とを熱で溶融させ両者を会合させて発色させる
原理を利用してつくられている。[Conventional technology: Heat sensitive. The principle behind recording materials is that an electron-accepting color-developing substance (hereinafter also referred to as a color-developing agent) and an electron-accepting color-developing substance (hereinafter abbreviated as a color-developing agent) are melted with heat and brought together to form a color. It is made using.
感熱記録材料は、近年、ファクシミリ％ ＰＯＳラベ
ルなど各種の記録用に用いられている。Thermosensitive recording materials have recently been used for various recording purposes such as facsimile % POS labels.
この発色剤としてはクリスタルバイオレットラクトンな
どのラクトン化合物が使用され、また顕色剤としては固
体酸性物質、フェノール化合物、有機酸またはそれらの
金属化合物などが用いられている。Lactone compounds such as crystal violet lactone are used as color formers, and solid acidic substances, phenol compounds, organic acids, or metal compounds thereof are used as color developers.
さらに、近年情報の高速化が著しく要望され、種々の高
速機器が開発されてきた。これに伴い高感度の感熱記録
用材料も開発されてきた。たとえば、発色剤、顕色剤に
併用して感度向上を計る方法として、アセト酢酸アニリ
ドの併用（特開昭５２−１０８７４８号）、アルキル化
ビフェニルの併用（特開昭５３−３９１３９号）、ステ
アリン酸アミドと飽和脂肪酸の併用（特開昭５４−１３
９７４０号）、フタル酸アルキルエステルの併用（特開
昭５７−１１１１ｉ６９０号）、フ．タル酸ジベンジル
エステルの併用（特開昭５８−９８２８５号）、シュウ
酸ジ（ｐ−プチルオキシカルボニルフェニル）の併川（
特開昭８２−８３１８４号）、シュウ酸ジベンジルエス
テル）の併用（特開昭８４−１５８３号）、芳香族多価
カルポン酸のポリアリーロキシアルキルエステルの併用
（特開昭６４−８７２９１号）など、感度の良い顕色剤
として、Ｐ−ヒドロキシ安息香酸（特開昭５４−７４７
８２号〉、ビスヒドロキシフェニル酢酸（特開昭５９−
７９７９３号）、２−（４−ヒドロキシフェニル）−２
−（３−イソブロビルー４−ヒドロキシフェニル）プロ
パン（％ｌＪ１１１？１５９−１７８０９４号）などが
報告されている。Furthermore, in recent years there has been a significant demand for faster information, and various high-speed devices have been developed. Along with this, highly sensitive heat-sensitive recording materials have also been developed. For example, methods for improving sensitivity by using color formers and developers in combination include acetoacetanilide (Japanese Unexamined Patent Publication No. 52-108748), alkylated biphenyl (Japanese Unexamined Patent Publication No. 53-39139), and stearin. Combined use of acid amide and saturated fatty acid (Unexamined Japanese Patent Publication No. 54-13
No. 9740), combined use of phthalic acid alkyl ester (JP-A-57-1111i690), F. Combined use of dibenzyl tarate (JP-A No. 58-98285), dibenzyl oxalate (p-butyloxycarbonylphenyl)
JP-A-82-83184), oxalic acid dibenzyl ester) (JP-A-84-1583), polyaryloxyalkyl ester of aromatic polycarboxylic acid (JP-A-64-87291) P-hydroxybenzoic acid (JP-A-54-747
No. 82>, bishydroxyphenylacetic acid (Unexamined Japanese Patent Publication No. 1983-
79793), 2-(4-hydroxyphenyl)-2
-(3-isobroby-4-hydroxyphenyl)propane (%lJ111?159-178094) and the like have been reported.
［発明が解決しようとする課題］
しかル、従来の感熱記録用材料はまだ発色感度が不十分
であり、感度アップによる副作用、すなわち白色度の低
下を免れない。[Problems to be Solved by the Invention] However, conventional heat-sensitive recording materials still have insufficient color development sensitivity, and cannot avoid side effects due to increased sensitivity, that is, a decrease in whiteness.
［課題を解決するための手段コ
本発明者らは、改善された高感度、高白色性を有する感
熱記録用材料を得るべく、鋭意検討した結果本発明に到
達した。[Means for Solving the Problems] The present inventors have arrived at the present invention as a result of intensive studies in order to obtain a heat-sensitive recording material having improved high sensitivity and high whiteness.
すなわち、本発明は一般式
Ｒｓ Ｏ− （ＸＯ）−−Ｒｅ （１）｛式中％Ｒ
ｌはフェノール類残基、Ｒｔは脂肪族炭化水素基、脂肪
族モノカルボン酸残基または、Ｒ ｓ （ Ｏ Ｘ ）
。ＯＲＪ［Ｒ３は脂肪族ジカルポン酸残基またはーＣＨ
２−であり、Ｒａはフェノール類残基； ただしＲ２が
Ｒ１ｉ肪燐あヒ水噴、秀！ｒ２，シ獅方赤モ１１１７％
冫斬残〜鳴店には、Ｒ＋は −ＯＲｓ基（Ｒｓは炭素
数６以下の炭化水素基である），一Ｎｏｔ基、−ＣＯＯ
Ｒｓ基、− Ｃ Ｏ Ｎ Ｈ Ｒ ｓ基および一〇ＯＲ
ｓ基からなる群よである）、−ＮＯ２基を有したフェノ
ール類残基であり、Ｒ２がーＲ ３（ Ｏ Ｘ ） −
０ Ｒ ａの場合はＲ＋および／またはＲａＬｊ−
ＯＲ＠基、一ＮＯ２基、−ＣＯＯＲ６基、− Ｃ Ｏ
Ｎ Ｈ Ｒ ｓ基および一ＣＯＲｓ基からなる群よで
ある）、−ＮＯ２基を有したフェノール類残基である］
、Ｘは低級アルキレン基、ｍおよびｎは１〜３の整数で
ある｝で表される化合物（Ａ）を電子受容性顕色性物質
と電子供与性無色発色剤とを熱溶融させ発色させる原理
に基づいた感熱記録用材料上に含有させてなることを特
徴とする感熱記録用材料である。That is, the present invention provides the general formula Rs O- (XO)--Re (1) {in the formula %R
l is a phenol residue, Rt is an aliphatic hydrocarbon group, an aliphatic monocarboxylic acid residue, or R s (O X )
. ORJ[R3 is an aliphatic dicarboxylic acid residue or -CH
2-, and Ra is a phenolic residue; however, R2 is R1i fatty phosphorus ahi water fountain, Hide! r2, shishikata red mo 1117%
In Meizan Zan~Meiten, R+ is -ORs group (Rs is a hydrocarbon group having 6 or less carbon atoms), -Not group, -COO
Rs group, -C O N H R s group and 10OR
s group), is a phenolic residue having -NO2 group, and R2 is -R3(OX)-
If 0 Ra, then R+ and/or RaLj−
OR@ group, -NO2 group, -COOR6 group, -C O
A group consisting of NHRs group and one CORs group), a phenol residue having -NO2 group]
, X is a lower alkylene group, and m and n are integers of 1 to 3} The principle of coloring the compound (A) represented by } by thermally melting an electron-accepting color-developing substance and an electron-donating colorless coloring agent. This is a heat-sensitive recording material characterized in that it is contained on a heat-sensitive recording material based on.
本発明に於て残基とは、ある化合物から一〇｝１基を除
いた基を意味する。In the present invention, the term "residue" refers to a group obtained by removing one group from a certain compound.
一般式０）において、Ｒ２がＦＩ％ｄ４’ｌｈＪ，４ｂ
ｉ（ＩＡ １ｎ＋ｓｐａＲＸｈモｌφぶ満残一には、Ｒ
１は −ＯＲｓ基（ Ｒ ｓは炭素数６以下の炭化水
素基である）、 Ｎｏｗ基、Ｃ ０ ０ Ｒ ｓ基、−
ＣＯＮＨＲｓ基および一〇ＯＲｓ基からなる群よである
）、−ＮＯ２基を有したフェノール類残基であり、Ｒ２
がーＲ ｓ （ Ｏ Ｘ ） − ０ Ｒ ａの場合は
Ｒ，および／またはＲ ４ １本−ＯＲｓ基、 ＮＯ
ｔ基、−ＣＯＯＲｓ基、− Ｃ Ｏ Ｎ Ｈ Ｒ ｓ基
および一〇Ｏ Ｒ ｓ基からなる群よである）、−ＮＯ
２基を有したフェノール類残基であり これらの異なっ
た基は複数個ベンゼン核またはナフタリン核へ置換され
ていてもよい。In general formula 0), R2 is FI%d4'lhJ,4b
i(IA 1n+spaRXhmolφ) is R
1 is -ORs group (Rs is a hydrocarbon group having 6 or less carbon atoms), Now group, C00Rs group, -
It is a group consisting of CONHRs group and 10ORs group), is a phenolic residue having -NO2 group, and R2
-R s (OX) - 0 In the case of Ra, R and/or R 4 -ORs group, NO
t group, -COORs group, -C O N H R s group and 10O R s group), -NO
It is a phenol residue having two groups, and a plurality of these different groups may be substituted with a benzene nucleus or a naphthalene nucleus.
上記置換基を有したフェノール類としては一般式
（Ｚ）ｈ− （Ａ ｒ） 一ＯＨ （１）［式中
、Ａｒはベンゼン核またはナフタリン核、Ｚは−ＯＲ＠
基、 −ＳＲｓ基、 − Ｃ ０ ０ Ｒ ｓ基、 一
ＣＯ Ｎ Ｈ Ｒ ｖ．基，−ＣＯＲｉ基（Ｒｓは炭素
数６以下の炭化水素基）．ＮＯ＊基、ＣＮ基、ｋは１〜
３の整数である。コで表される化合物があげられる。一
般式（１）において、Ｒｓの炭素数６以下の炭化水素と
してはメチル、エチル、ｎ−プロビル、イソプロビル、
ｎ−ブチル、イソブチル、ｓｅｃ−ブチル．ｔｅｒｔ−
ブチル、ぺ冫チル、ヘキシノレなどの直鎖または分岐の
アルキル基； ビニル、アリル、ブロペニル、インプロ
ペニル、２−ブテニル、エチニル、２−プロビニルなど
の直鎖または分岐のアアルケニル基およびアルキニル基
； フェニル、シクロペンチル、シクロヘキシル基など
の炭素環式基をあげることができる。Phenols having the above substituents have the general formula (Z)h- (Ar) 1OH (1) [wherein, Ar is a benzene nucleus or naphthalene nucleus, and Z is -OR@
group, -SRs group, -C00Rs group, -CONHR v. group, -CORi group (Rs is a hydrocarbon group having 6 or less carbon atoms). NO* group, CN group, k is 1~
It is an integer of 3. Examples include compounds represented by . In general formula (1), the hydrocarbons having 6 or less carbon atoms in Rs include methyl, ethyl, n-propyl, isopropyl,
n-butyl, isobutyl, sec-butyl. tert-
Straight chain or branched alkyl groups such as butyl, pentyl, hexynol; straight chain or branched aalkenyl and alkynyl groups such as vinyl, allyl, propenyl, impropenyl, 2-butenyl, ethynyl, 2-provinyl; phenyl , cyclopentyl, cyclohexyl and other carbocyclic groups.
好ましくはメチル、ｔｅｒｔ−ブチル、アリル、フェニ
ル基である。Preferred are methyl, tert-butyl, allyl, and phenyl groups.
置換基を有したフェノール類の化合物を具体的に示すと
次のとうりである。Specific examples of phenolic compounds having substituents are as follows.
０−メトキシフェノール、ｐ一エトキシフェノール、４
−メトキシ−１−ナフトールなどのアルコキシ化フェノ
ールおよびアルコキシ化ナフトール； ４−メチルチオ
フェノール、４−エチルチオフェノール、４−メチルチ
オーｌ−ナフトールなどのアルコチオキシ化フェノール
およびアルコチオキシ化ナフトール； ｐ−ヒドロキシ
安息香酸メチルエステル、ｍ−ヒドロキシ安息香酸エチ
ルエステル、０−ヒドロキシ安Ｊｉ香酸フェニルエステ
ル、ｐ−ヒドロキシ安息香酸シクロヘキシルエステル、
２−ヒドロキシル−３−ナフトエ酸メチルエステル、２
−ヒドロキシル−３−ナフトエ酸フェニルエステルなど
のアルコキシカルボニル化フェノールおよびアルコキシ
カルボニル化ナフトール； ２−ヒドロキシ安息香酸メ
チルアミド、２ーヒドロキシ安息香酸エチルアミド、２
−ヒドロキシ安息香酸アリルアミド、２−ヒドロキシ安
息香酸アニリド、２−ヒドロキシ−３−ナフトエ酸メチ
ルアミド、２−ヒドロキシ−３−ナフトエ酸アニリドな
どのアルキルアミノカルボニル化フェノールおよびアル
キルアミノカルボニル化ナフトーノレ； ４−ヒドロキ
シフェニノレメチノレケトン、２−ヒドロキシフェニル
エチルケトン、２−ヒドロキシベンゾフェノン、４−ヒ
ドロキシベンゾフェノン、２−ヒドロキシナフチルメチ
ルケトンなどのアシル化フェノールおよびアシル化ナフ
トール；ｍ−ニトロフェノール、０−二トロフェノール
、ｐ−ニトロフェノール、２． ４−シニトロフェノ
ール、２．６−ジニトロフェノール、２，５−ジニトロ
フェノール、１一二トロナフトール、２．４−ジニトロ
ナフトールなどのニトロ化フェノールおよび二トロ化ナ
フトール：゜Ｏ−シアノフェノール、ｐ−シアノフェノ
ール、１−シアノ−２一ナフトールなどのシアノ化フェ
ノールおよびシアノ化ナフトールなどがあげられる。0-methoxyphenol, p-ethoxyphenol, 4
- alkoxylated phenols and naphthols such as methoxy-1-naphthol; alkoxylated phenols and naphthols such as 4-methylthiophenol, 4-ethylthiophenol, 4-methylthiol-1-naphthol; p-hydroxybenzoic acid methyl ester , m-hydroxybenzoic acid ethyl ester, 0-hydroxybenzoic acid phenyl ester, p-hydroxybenzoic acid cyclohexyl ester,
2-hydroxyl-3-naphthoic acid methyl ester, 2
-Alkoxycarbonylated phenols and alkoxycarbonylated naphthols such as hydroxyl-3-naphthoic acid phenyl ester; 2-hydroxybenzoic acid methylamide, 2-hydroxybenzoic acid ethylamide, 2
- alkylaminocarbonylated phenols and alkylaminocarbonylated naphthonoles such as hydroxybenzoic acid allylamide, 2-hydroxybenzoic acid anilide, 2-hydroxy-3-naphthoic acid methylamide, 2-hydroxy-3-naphthoic acid anilide; 4-hydroxyphenylated Acylated phenols and naphthols such as noremethynoleketone, 2-hydroxyphenylethylketone, 2-hydroxybenzophenone, 4-hydroxybenzophenone, 2-hydroxynaphthylmethylketone; m-nitrophenol, 0-nitrophenol, p -nitrophenol, 2. Nitrated phenols and ditrated naphthols such as 4-sinitrophenol, 2,6-dinitrophenol, 2,5-dinitrophenol, 1-dinitronaphthol, 2,4-dinitronaphthol: ゜O-cyanophenol, p -cyanophenol, cyanated phenol such as 1-cyano-2-naphthol, and cyanated naphthol.
置換基を有したフェノール類の好ましい置換基は−ＯＲ
ｓ基、−ＣＯＯＲｉ基、− Ｃ Ｏ Ｎ Ｈ Ｒ ｓ基
、− Ｃ Ｏ Ｒ ｓ基、ＮＯ２基である。A preferred substituent of the phenols having a substituent is -OR
s group, -COORi group, -CONHRs group, -CORs group, and NO2 group.
Ｒ２の脂肪族炭化水素基としては、炭素数１以上、好ま
しくは１−１８の直鎖または分岐のアルキル基、または
炭素数２以上、好ましくは２〜２２のアルケニル基があ
げられる。Examples of the aliphatic hydrocarbon group for R2 include a linear or branched alkyl group having 1 or more carbon atoms, preferably 1-18 carbon atoms, or an alkenyl group having 2 or more carbon atoms, preferably 2-22 carbon atoms.
アルキル基としては、メチル、エチル、プロビル、ブチ
ル、ヘキシル、ヘプチル、オクチル、インオクチル、デ
シノレ、ドデシノレ、ぺ冫タデシノレ、ヘキサデシル、
ヘプタデシル、オクタデシル基などが、またアルケニル
基としてはドデセニル、オクタデセニル基などがあげら
れる。Examples of alkyl groups include methyl, ethyl, proyl, butyl, hexyl, heptyl, octyl, inoctyl, decyl, dodecyl, peptyl, hexadecyl,
Examples of the alkenyl group include heptadecyl and octadecyl groups, and examples of the alkenyl group include dodecenyl and octadecenyl groups.
Ｒ２の脂肪族モノカルボン酸残基を構成する脂肪族モノ
カルボン酸としては、炭素数が通常！〜３０，好ましく
は８〜２０の直鎖または分岐の飽和または不飽和脂肪族
モノカルボン酸、たとえばギ酸、酢酸、プロビオン酸、
カプロン酸、カブリン酸、ラウリ冫酸、ミリスチン酸、
パルミチン酸、ステアリン酸、イソステアリン酸、エル
シン酸などの飽和脂肪族モノカルボン酸； オレイン酸
、リノール酸、リノレイン酸などの不飽和脂肪族モノカ
ルボン酸；および牛脂脂肪酸、パーム油脂肪酸、大豆油
脂肪酸などの天然油脂より７８られる脂肪族モノカルボ
ン酸があげられる。これらのうちで好ましいものは、８
〜２０の飽和または不飽和モノカルボン酸であり、特に
好ましいものはステアリン酸である。The aliphatic monocarboxylic acid constituting the aliphatic monocarboxylic acid residue of R2 usually has the number of carbon atoms! ~30, preferably 8 to 20 linear or branched saturated or unsaturated aliphatic monocarboxylic acids, such as formic acid, acetic acid, probionic acid,
caproic acid, capric acid, lauric acid, myristic acid,
Saturated aliphatic monocarboxylic acids such as palmitic acid, stearic acid, isostearic acid, and erucic acid; Unsaturated aliphatic monocarboxylic acids such as oleic acid, linoleic acid, and linoleic acid; and beef tallow fatty acid, palm oil fatty acid, soybean oil fatty acid, etc. 78 aliphatic monocarboxylic acids derived from natural oils and fats. Among these, preferred are 8
~20 saturated or unsaturated monocarboxylic acids, particularly preferred is stearic acid.
Ｒ，（７） シカルポン酸残基を構成するジカルボン酸
としては、炭素数２〜１Ｂのジカルポン酸、たとえばシ
ュウ酸、マロン酸、コハク酸、グルタル酸、アジビン酸
などの脂肪族飽和ジカルボン酸（酸無水物でもよい）；
ハロゲノマロン酸、八ロゲノコハク酸、トリブロムコ
ハク酸などのハロゲノジカルボン酸； メチルコハク酸
、α−メチルグルタル酸、β−メチルグルタル酸などの
アルキル置換ジカルボン酸； マレイン酸、フマル酸
、イタコン酸、シトラコン酸、メサコン酸、グルタ，コ
ン酸、ムコン酸、シスーシスムコン酸、カロチノイド、
，アセチレンジカルポン酸などの脂肪族不飽和ジカルボ
ン酸やこれらジカルボン酸とメチル、エチル、プロビル
アルコールなどの低級アルコールとのエステルなどをあ
げることができる。これらのうち好ましくは、シュウ酸
、フマル酸、マロン酸、ｍ水コハク酸および無水マレイ
ン酸である。R, (7) Dicarboxylic acids constituting the dicarboxylic acid residue include dicarboxylic acids having 2 to 1B carbon atoms, such as aliphatic saturated dicarboxylic acids (acids) such as oxalic acid, malonic acid, succinic acid, glutaric acid, adivic acid, may be anhydrous);
Halogenodicarboxylic acids such as halogenomalonic acid, octarogenosuccinic acid, and tribromosuccinic acid; Alkyl-substituted dicarboxylic acids such as methylsuccinic acid, α-methylglutaric acid, and β-methylglutaric acid; maleic acid, fumaric acid, itaconic acid, and citraconic acid , mesaconic acid, gluta, conic acid, muconic acid, ciscismuconic acid, carotenoid,
, aliphatic unsaturated dicarboxylic acids such as acetylene dicarboxylic acid, and esters of these dicarboxylic acids and lower alcohols such as methyl, ethyl, and proyl alcohol. Among these, oxalic acid, fumaric acid, malonic acid, m-hydrosuccinic acid and maleic anhydride are preferred.
Ｘの低級アルキレン基としては、炭素数２〜４のアルキ
レン基たとえば、エチレン、プロピレン、あるいはブチ
レン基があげられ、好ましくはエチレン基である。Examples of the lower alkylene group for X include alkylene groups having 2 to 4 carbon atoms, such as ethylene, propylene, or butylene groups, with ethylene being preferred.
ｍおよびｎは好ましくは夏である。m and n are preferably summer.
一般式（１）で示される化合物（Ａ）を具体的に示せば
下記の通りである。The specific examples of the compound (A) represented by the general formula (1) are as follows.
置換基を有したフェノール類はフェノール類と略記した
。Phenols with substituents are abbreviated as phenols.
［１Ｆ（ポリ）アルキレングリコールフェニル類エーテ
ルと脂肪族アルコールとのジエーテル
［：２］（ポリ〉アルキレングリコールフェニル類エー
テルと脂肪族モノカルボン酸とのモノエステル［３］（
ポリ）アルキレングリコールフェニル類エーテルと脂肪
族ジカルポン酸とのジエステル［４］（ポリ）アルキレ
ングリコールフェニル類エーテルとホルマリンとのジア
セタール
などがあげられる。[1F (Poly)Diether of alkylene glycol phenyl ether and aliphatic alcohol [:2] (Monoester of poly(poly)alkylene glycol phenyl ether and aliphatic monocarboxylic acid [3] (
Diesters of poly)alkylene glycol phenyl ethers and aliphatic dicarboxylic acids [4] Diacetals of (poly)alkylene glycol phenyl ethers and formalin, and the like.
化合物（Ａ）は種類の異なるものを二種以上併用しても
よい。Two or more different types of compounds (A) may be used in combination.
一般式（１）で表される化合物（Ａ）、いわゆる増感剤
、は任意の方法で製造することができ、たとえば置換基
を有したフェノール類にアルキレンオキサイドを付加さ
せＣ （ＸＯ） １１１ （ＯＸ） ．を構成］、次
いでジカルボン酸類を反応させて（Ｒ２を構成）、ジエ
ステル化することによって得ることができる。The compound (A) represented by the general formula (1), a so-called sensitizer, can be produced by any method. For example, by adding alkylene oxide to a phenol having a substituent, C (XO) 111 ( OX). ] and then react with dicarboxylic acids (constituting R2) to diesterify.
置換基を有したフェノール類にアルキレンオキサイドを
付加させる方法は公知の方法、たとえば苛性ソーダ、苛
性カリ、金属ナトリウム、メチラ一トなどのアルカリ性
触媒を用い、加圧下、１６０〜１９０℃で付加させるこ
とにより行うことができる。The alkylene oxide can be added to a phenol having a substituent using a known method, for example, by using an alkaline catalyst such as caustic soda, caustic potash, metallic sodium, or methylate under pressure at 160 to 190°C. be able to.
アルキレンオキサイドの付加モル数はｍおよびｎが１〜
３の範囲で任意に変えうるがそれぞれｌが好ましい。The number of moles of alkylene oxide added is m and n from 1 to
It can be changed arbitrarily within the range of 3, but 1 is preferable in each case.
置換基を有したフェノール類のポリオキシアルキレン付
加物とジカルボン酸類との反応は通常の方法、たとえば
硫酸、ｌ）−｝ルエンスルホン酸、燐酸などの酸性触媒
または苛性ソーダ、苛性カリな１５０〜２５０℃で反応
を行うことができる。The reaction between a polyoxyalkylene adduct of a phenol having a substituent and a dicarboxylic acid can be carried out using a conventional method, for example, using an acidic catalyst such as sulfuric acid, l)-}luenesulfonic acid, or phosphoric acid, or using caustic soda or caustic potassium at 150 to 250°C. reactions can be carried out.
本発明の感熱記録用材料において、 一般式（ｌ）で示
される化合物（Ａ）の使用ｍは顕色剤１００部に対して
、通常１〜２００重量部、好ましくは３〜ｌＯＯｍ量部
、特に好ましくは１０〜？Ｏｆｆｉ量部の範囲である。In the heat-sensitive recording material of the present invention, the amount of the compound (A) represented by the general formula (l) is usually 1 to 200 parts by weight, preferably 3 to 100 m parts, particularly Preferably 10~? Offi quantity range.
化合物（Ａ）の使用量が！未満では感熱記録としての感
度向上効果に乏し＜、２００を越えると感度向上効果は
もはや飽和状態にあり不経済である。The amount of compound (A) used! If it is less than 200, the effect of improving sensitivity in thermal recording is poor, and if it exceeds 200, the effect of improving sensitivity is already saturated and is uneconomical.
本発明の感熱記録用材料にわいて記録層上を構成する発
色剤としては、従来の感熱または感圧記録材料に使用さ
れているものを使用することができる。たとえばトリア
リールメタン系、ジフェニルメタン系、キサンテン系、
フェノチアジン系、スピロビラン系などの発色剤が好ま
しく用い６れる。As the coloring agent constituting the recording layer in the heat-sensitive recording material of the present invention, those used in conventional heat-sensitive or pressure-sensitive recording materials can be used. For example, triarylmethane, diphenylmethane, xanthene,
Coloring agents such as phenothiazine type and spirobilane type are preferably used6.
トリアリールメタン系発色剤としては、３・３−ビス（
ｐ−ジメチルアミノフェニル）一Ｂ−ジメチルアミノフ
タリド（クリスタルバイオレットラクトン以下ＣＶＬと
略記ｄ、３・３−ビス（ｐ−ジメチルアミノフェニル）
フタリド、３−（ｐ−ジメチルアミノフェニル）−３−
（１・２−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）一３−（２−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−フェニルインドール−
３−イル）フタリド、３・３−ビス（１・２−ジメチノ
レインドール−３−イノレ）−５−ジメチルアミノフタ
リド、３・３−ビスー（ｌ・２−ジメチルイ・冫ドーノ
レ−３−イノレ）一トジメチノレアミノフタリド、３・
３−ビス（トエチルカルパゾール−３−イル）−５−ジ
メチルアミノフタリド、３・３−ビス（２−フェニルイ
ンドール−３−イル）一トジメチルアミノフタリド、３
−ｐ−ジメチルアミノフェニル−３−（１−メチルビロ
ール−２−イル）一トジメチルアミノフタリドなどがあ
げられる。As a triarylmethane coloring agent, 3,3-bis(
p-dimethylaminophenyl) -B-dimethylaminophthalide (crystal violet lactone, hereinafter abbreviated as CVL, d,3,3-bis(p-dimethylaminophenyl)
Phthalide, 3-(p-dimethylaminophenyl)-3-
(1,2-dimethylindol-3-yl)phthalide,
3-(p-dimethylaminophenyl)-3-(2-methylindol-3-yl)phthalide, 3-<p-dimethylaminophenyl)-3-(2-phenylindole-
3-yl)phthalide, 3,3-bis(1,2-dimethynoreindol-3-inole)-5-dimethylaminophthalide, 3,3-bis(l,2-dimethyl-3-inole) ) Monodimethynoleaminophthalide, 3.
3-bis(toethylcarpazol-3-yl)-5-dimethylaminophthalide, 3,3-bis(2-phenylindol-3-yl)-dimethylaminophthalide, 3
-p-dimethylaminophenyl-3-(1-methylpyrrol-2-yl) monotodimethylaminophthalide and the like.
ジフェニルメタン系発色剤としては、４・４′−ビスジ
メチルアミノペンズヒドリンベンジルエーテル、Ｎ−ハ
ロフェニルロイコオーラミン、Ｎ−２・４・５−トリク
ロロフェニルロイコオーラミンなどがあげられる。Examples of diphenylmethane color formers include 4,4'-bisdimethylaminopenzhydrin benzyl ether, N-halophenylleucoauramine, and N-2,4,5-trichlorophenylleucoauramine.
キサンテン系発色剤としては、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、３
−ジメチルアミノー６−メトキシフルオラン、３−シエ
チルアミノー７−メトキシフルオラン、３−ジエチルア
ミノー７−クロローＢ−メチルフルオラン、３−ジエチ
ルアミノー７−（アセチルメチルアミノ）フルオラン、
３−ジエチノレアミノ−７−（ジベンジルアミノ）フノ
レヘオラン、３−ジエチルアミノー７−（メチルベンジ
ルアミノ）フルオラン、３−ジエチルアミノー７−（ク
ロロエチルメチノレアミノ）フルオラン、３−ジエチル
アミノー７−（ジエチルアミノ）フルオランなどがあげ
られる。As the xanthene coloring agent, rhodamine B-anilinolactam, rhodamine B (p-nitroanilino)lactam, rhodamine B (p-chloroanilino)lactam, 3
-dimethylamino-6-methoxyfluorane, 3-ethylamino-7-methoxyfluorane, 3-diethylamino-7-chloroB-methylfluorane, 3-diethylamino-7-(acetylmethylamino)fluorane,
3-diethylamino-7-(dibenzylamino)funoleheolan, 3-diethylamino-7-(methylbenzylamino)fluoran, 3-diethylamino-7-(chloroethylmethylamino)fluoran, 3-diethylamino-7-(diethylamino) Examples include fluoran.
フェノチアジン系発色剤としては、べ冫ゾイルロイコメ
チレンブルー ｐ−ニトロベンゾイルロイコメチレンブ
ルーなどがあげられる。Examples of the phenothiazine coloring agent include benzyl leucomethylene blue, p-nitrobenzoyl leucomethylene blue, and the like.
スピロピラン系発色剤としては、３−メチルースビロー
ジナフトピラン、３−エチルースピロージナフトビラン
、３・３′−ジクロロースピロージナフトピラン、３一
ペンジルースビロージナフトピラン、３−メチルーナフ
ト−（３−メトキシーベンゾ）一スピロビラン、３−プ
ロピノレースビロージベンゾジビランなどがあげられる
。Examples of spiropyran-based coloring agents include 3-methylsuvirozinaphthopyran, 3-ethylsupirozinaphthopyran, 3,3'-dichlorospirosinaphthopyran, 3-penzylosuvirozinaphthopyran, and 3-methylnaphthopyran. Examples include (3-methoxybenzo)-spirobilane and 3-propinolacevirodibenzodibiran.
これらの発色剤は単独でまたは２Ｎ以上混合して用いて
もよい。These coloring agents may be used alone or in a mixture of 2N or more.
一方、顕色剤としては、発色剤に対して加熱時に反応し
てこれを発色させる種々の電子受容性物質が適用される
。このような電子受容性物質としてはフェノール性物質
、有機または無機の酸性物質あるいはその塩などが使用
でき、その具体例としては下記のものがあげられる。On the other hand, as the color developer, various electron-accepting substances that react with the color former when heated to develop color can be used. As such an electron-accepting substance, a phenolic substance, an organic or inorganic acidic substance, or a salt thereof can be used, and specific examples thereof include the following.
たとえば、没食子酸、サリチル酸， ３−１ｓｏ−プ
ロビルサリチル酸、３−シクロへキシルサリチル酸、３
・５−ジーｔａｒｔ−プチルサリチル酸、３・５−ジー
α−メチルベンジルサリチル酸などの置換サリチル酸；
４・４′−イソプロピリデンフェノール，４・４′−イ
ンプロビリデンビス（２−クロロフェノール）、４・４
′−インプロピリデンビス（２・トジブロモフェノール
）、４・４′−イソプロピリデンビス（２・６−ジクロ
口フェノール）、４・４′−インプロピリデンビス（２
−メチノレフェノーノレ）、４・４′−イソブロピリデ
ンビス（２・６−ジメチノレフェノール）、４・４’−
ｓｅｅ−プチリデンジフェノール、４・４′−イソプロ
ピリデンビス（２−ｔｅｒｔ−プチノレフェノール）、
４・４′−シクロヘキシリデンジフェノール、４・４′
−シクロヘキシリデンビス（２−メチノレフェノール）
，１ ４−ｔｅｒｔ−プチルフェノール、４−フェニル
フェノ一ル、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、３・５−キシレノール、チ
モール、メチル−４−ヒドロキシベンゾエート、４−ヒ
ドロキシアセトフェノン、ニボラック型フェノール樹脂
、２・２′−チオビス（４・Ｂ−ジクロロフェノール）
、カテコーノレ、レゾルシン、ヒドロキノン、フロログ
リシン、フロログリシンカルポン酸， ４−ｔａｒｔ
−オクチルカテコーノレ、２・２′−メチレンビス（←
クロロフェノーノレ）、２・２’−メチレンビス（４−
メチルーｓ−ｔａｒｔプチルフェノール）、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ビル、ｐ−ヒドロキシ
安息香酸プチル、Ｐ−ヒドロキシ安息香酸−ｎ−オクチ
ル、ｐ−ヒドロキシ安息香酸ベンジル（以下ＰＯＢと略
記）、ｐ−ヒドロキシ安息香酸一ｐ−クロロベンジル、
ｐ−ヒドロキシ安息香酸−ｏ−’ｙロロベンジル、ｐ−
ヒドロキシ安息香酸−ｐ−メチルベンジル、サリチル酸
亜鉛、ｌ−ヒドロキシ−２−ナフトエ酸、２−ヒドロキ
シートナフトエＭ、２−ヒドロキシートナフトエ酸亜鉛
、４−ヒドロキシジフェニルスルフォン、４−ヒドロキ
シ−４′−クロロジフェニルスルフォン、ビス（４−ヒ
ドロキシフェニル）スルフィド、２−ヒドロキシ−Ｐ−
トルイル酸、３・５−シ−ｔｅｒｔ−プチルサリチル酸
亜鉛、３・５−ジーｔｅｒｔ−プチルサリチル酸亜鉛、
安息香酸、酒石酸、シュウ酸、コハク酸、ステアリン酸
、クエン酸、マレイン酸、４−ヒドロキシフタル酸、ホ
ウ酸などである。For example, gallic acid, salicylic acid, 3-1so-probylsalicylic acid, 3-cyclohexylsalicylic acid, 3
- Substituted salicylic acids such as 5-di-tart-butylsalicylic acid and 3,5-di-α-methylbenzylsalicylic acid;
4,4'-isopropylidenephenol, 4,4'-impropylidene bis(2-chlorophenol), 4,4
'-Impropylidene bis (2-dibromophenol), 4,4'-isopropylidene bis (2,6-dichlorophenol), 4,4'-impropylidene bis (2-dibromophenol),
-methynolephenol), 4,4'-isobropylidene bis(2,6-dimethynolephenol), 4,4'-
see-butylidene diphenol, 4,4'-isopropylidene bis(2-tert-butylidenephenol),
4,4'-cyclohexylidene diphenol, 4,4'
-Cyclohexylidenebis(2-methynolephenol)
, 1 4-tert-butylphenol, 4-phenylphenol, 4-hydroxydiphenoxide, α-naphthol, β-naphthol, 3,5-xylenol, thymol, methyl-4-hydroxybenzoate, 4-hydroxyacetophenone, Nivolac type phenolic resin, 2,2'-thiobis(4,B-dichlorophenol)
, catechone, resorcinol, hydroquinone, phloroglycin, phloroglycincarboxylic acid, 4-tart
-Octylcatechonole, 2,2'-methylenebis(←
chlorophenol), 2,2'-methylenebis(4-
methyl-s-tartbutylphenol), 2,2'-
Dihydroxydiphenyl, ethyl p-hydroxybenzoate, probyl p-hydroxybenzoate, butyl p-hydroxybenzoate, n-octyl p-hydroxybenzoate, benzyl p-hydroxybenzoate (hereinafter abbreviated as POB), p-hydroxy monop-chlorobenzyl benzoate,
p-Hydroxybenzoic acid-o-'y lolobenzyl, p-
p-methylbenzyl hydroxybenzoate, zinc salicylate, l-hydroxy-2-naphthoic acid, 2-hydroxynaphthoic acid M, zinc 2-hydroxynaphthoate, 4-hydroxydiphenylsulfone, 4-hydroxy-4'-chloro Diphenylsulfone, bis(4-hydroxyphenyl)sulfide, 2-hydroxy-P-
Toluic acid, zinc 3,5-tert-butylsalicylate, zinc 3,5-tert-butylsalicylate,
These include benzoic acid, tartaric acid, oxalic acid, succinic acid, stearic acid, citric acid, maleic acid, 4-hydroxyphthalic acid, and boric acid.
これらの顕色剤は単独または２Ｗ以上混合して用いても
よい。These color developers may be used alone or in a mixture of 2W or more.
発色剤と顕色剤の使用比率は、発色剤１００重量部に対
して、顕色剤は通常５〜１００重量部、好ましくは１０
〜７０重量部、特に好ましくは２０〜５０重量部である
。顕色剤の使用量が５重量部未満の場合は所望の発色濃
度がです、また１００重量部を越えると発色濃度は平衡
に達し、もはやこれ以上の使用は不経済である。The ratio of the color former to the color developer is usually 5 to 100 parts by weight, preferably 10 parts by weight per 100 parts by weight of the color former.
~70 parts by weight, particularly preferably 20-50 parts by weight. If the amount of color developer used is less than 5 parts by weight, the desired color density will be low, and if it exceeds 100 parts by weight, the color density will reach equilibrium and it is no longer economical to use any more.
次に本発明の感熱記録用材料の製造法について述べる。Next, a method for producing the heat-sensitive recording material of the present invention will be described.
本発明にわける化合物（Ａ）、または発色剤、または顕
色剤を別々に分散し懸濁溶液を製造する。A suspension solution is prepared by separately dispersing the compound (A) according to the present invention, a color former, or a color developer.
続いてそれぞれの！！！！濁溶液を混合し、該混合物（
塗工液）を支持体に塗工し感熱記録用材料を製造する。Next, each! ! ! ! Mix the cloudy solution and add the mixture (
Coating liquid) is coated on a support to produce a heat-sensitive recording material.
詳細には、本発明における化合物（Ａ）、または発色剤
、または顕色剤と結合剤を水中で必要ならば界面活性剤
（２−エチルへキシルスルホサクシネートソーダ塩、ナ
フタレンスルホン酸ソーダ塩ホルマリン綜合物など）と
共にポールミル、アトライダーまたはサンドグラインダ
ーなどの粉砕機によってｌＯμ以下、好ましくは３μ以
下の粒子に扮砕、分散し塗工液とする。場合によっては
本発明における化合物（Ａ）、または発色剤、または顕
色剤を前もって微粉状態に細粉砕してから結合剤、界面
活性剤などを含む水中で分散し塗工液としてもよい。In detail, the compound (A) of the present invention, or a color former, or a color developer and a binder, is mixed in water with a surfactant (2-ethylhexyl sulfosuccinate sodium salt, naphthalene sulfonate sodium salt, formalin), if necessary. A coating liquid is obtained by crushing and dispersing the particles together with a pulverizer such as a pole mill, an atrider, or a sand grinder into particles of 10μ or less, preferably 3μ or less. In some cases, the compound (A), color former, or color developer of the present invention may be pulverized in advance into a fine powder and then dispersed in water containing a binder, a surfactant, etc. to prepare a coating solution.
上記結合剤としては、ポリビニルアルコール、デンプン
およびその誘導体、メトキシセルロース、ヒドロキシエ
チルセルロース、カルボキシメチルセルロース、メチル
セルロース、エチルセルロースなどのセルロース誘導体
；ポリアクリル酸ソーダ、ポリビニルビロリドン、アク
リル酸アミド／アクリル酸エステル共重合体、アクリル
酸アミド／アクリル酸エステル／メタアクリル酸３元共
重合体、スチレン／無水マレイン酸共重合体アルカリ塩
、インブチレン／無水マレイン酸共重合体アルカリ塩、
ポリアクリルアミド、アルギン酸ソーダ、ゼラチン、カ
ゼインなどの水溶性高分子の他、ポリ酢酸ビニル、ポリ
ウレタン、スチレン／ブタジエン共重合体、ポリアクリ
ル酸、ポリアクリル酸エステル、塩化ビニル／酢酸ビニ
ル共重合体、ポリブチルメタクリレート、エチレン／酢
酸ビニル共重合体、スチレン／ブタジエン／アクリル系
共重合体などのラテックスを用いることができる。Examples of the binder include polyvinyl alcohol, starch and its derivatives, cellulose derivatives such as methoxycellulose, hydroxyethylcellulose, carboxymethylcellulose, methylcellulose, and ethylcellulose; polysodium acrylate, polyvinylpyrrolidone, and acrylic acid amide/acrylic ester copolymer. acrylamide/acrylic ester/methacrylic acid ternary copolymer, styrene/maleic anhydride copolymer alkali salt, imbutylene/maleic anhydride copolymer alkali salt,
In addition to water-soluble polymers such as polyacrylamide, sodium alginate, gelatin, and casein, polyvinyl acetate, polyurethane, styrene/butadiene copolymer, polyacrylic acid, polyacrylic ester, vinyl chloride/vinyl acetate copolymer, and Latex such as butyl methacrylate, ethylene/vinyl acetate copolymer, styrene/butadiene/acrylic copolymer, etc. can be used.
塗工液は各化合物の懸濁溶液を下記表−１で示すように
組み合わせて混合する。The coating solution is prepared by combining suspension solutions of each compound as shown in Table 1 below.
表−１
表一ｌのＯ印はたとえば塗工液（ｂ）は本発明における
化合物（Ａ）の懸濁溶液と発色剤の懸濁溶液を混合する
ことを意味する。Table 1 The O mark in Table 1 means that, for example, the coating liquid (b) is a mixture of a suspension solution of the compound (A) in the present invention and a suspension solution of a color former.
また各塗工液に必要に応じてこの種の感熱記録材料に普
通に用いられている補助添加成分、たとえば填料、熱可
融性物質、潤滑剤などを併用することができる。填料と
しては、たとえば炭酸カルシウム、シリカ、酸化亜鉛、
酸化チタン、水酸化アルミニウム、水酸化亜鉛、硫酸バ
リウム、クレカオリン、タルク、表面処理された炭酸カ
ルシウムやシリカなどの無機系微粉末の他、尿素／ホル
マリン樹脂、スチレン／メタクリル酸共重合体、ボリス
チレン樹脂などの有機系の微粉末があげられる。熱可融
性物質、潤滑剤としては、たとえば高級脂肪酸またはそ
のエステル、アミドもしくは金属塩の他、各種ワックス
類、芳香族カルボン酸とアミンとの縮合物、安息香酸フ
ェニルエステル、高級直鎖グリコール、３・４−エポキ
シーへキサヒドロフタル酸ジアルキル、高級ケトン、そ
の他の熱可融性物質などの５０〜２００℃程度の融点を
有するものがあげられる。Further, each coating liquid may contain, if necessary, auxiliary additive components commonly used in this type of heat-sensitive recording material, such as fillers, thermofusible substances, lubricants, and the like. Examples of fillers include calcium carbonate, silica, zinc oxide,
In addition to inorganic fine powders such as titanium oxide, aluminum hydroxide, zinc hydroxide, barium sulfate, crekaolin, talc, and surface-treated calcium carbonate and silica, urea/formalin resin, styrene/methacrylic acid copolymer, and polystyrene resin Examples include organic fine powders such as. Examples of thermofusible substances and lubricants include higher fatty acids or their esters, amides, or metal salts, as well as various waxes, condensates of aromatic carboxylic acids and amines, benzoic acid phenyl esters, higher linear glycols, Examples include dialkyl 3,4-epoxy hexahydrophthalate, higher ketones, and other thermofusible substances having a melting point of about 50 to 200°C.
支持体は紙、合成紙、合成樹脂フィルムなどがあげられ
るが、紙が好ましい。Examples of the support include paper, synthetic paper, and synthetic resin film, with paper being preferred.
塗工方法としては下記ＣＩ）〜（■）の方法で行うこと
ができる。すなわち、支持体に先の塗工液（ａ）〜（ｇ
）をエアナイフコーター ブレンドコーター 口−ルコ
ーター ワイブプレスなどの方法により感熱記録層を形
成することができる。As a coating method, the following methods CI) to (■) can be used. That is, the coating liquids (a) to (g) are applied to the support.
) can be used to form a heat-sensitive recording layer using a method such as an air knife coater, blend coater, mouth coater, or wipe press.
（Ｉ）支持体上に塗工液（ａ）を塗工する。第１図に得
られた感熱記録用材料を示す。第１図において、１は支
持体、２は化合物（Ａ）と発色剤と顕色剤の鹿合した層
である。(I) Coating the coating liquid (a) onto the support. FIG. 1 shows the heat-sensitive recording material obtained. In FIG. 1, 1 is a support, and 2 is a layer of compound (A), a color former, and a color developer.
（ＩＩ）支持体上に塗工液（ｄ）を塗工しさらにその上
層に塗工液（ｅ）を塗エする。第２図に得られた感熱記
録用材料を示す。第２図において、５は発色剤と顕色剤
の混合した層、６は化合物（Ａ）の層である。(II) Coating liquid (d) is applied onto the support, and coating liquid (e) is further applied on top of the coating liquid (d). FIG. 2 shows the heat-sensitive recording material obtained. In FIG. 2, 5 is a layer containing a mixture of a color former and a color developer, and 6 is a layer of compound (A).
（ＩＩＩ）支持体上に塗工液（ｅ）を塗工し、さらにそ
の上層に塗工液（ｄ）を塗工する。第３図に得られた感
熱記録用材料を示す。第３図において、６は化合物（Ａ
）の層、５は発色剤と顕色剤の混合した層である。(III) Coating liquid (e) is applied onto the support, and coating liquid (d) is further applied on top of the coating liquid (e). FIG. 3 shows the heat-sensitive recording material obtained. In Figure 3, 6 is a compound (A
), layer 5 is a layer containing a mixture of a color former and a color developer.
（ＩＶ）支持体上に塗工液（ｇ）、塗工液（ｅ）、塗工
液Ｃｆ＞を順次積層するように塗工する。第４図に得ら
れた感熱記録用材料を示す。第４図において、８は顕色
剤の層、６は化合物（Ａ）の一層、７は発色剤の層であ
る。(IV) Coating liquid (g), coating liquid (e), and coating liquid Cf> are sequentially coated onto the support so as to be laminated. FIG. 4 shows the heat-sensitive recording material obtained. In FIG. 4, 8 is a color developer layer, 6 is a layer of compound (A), and 7 is a color former layer.
（Ｖ）支持体上に塗工液（ｆ）、塗工液（ｅ）、塗工液
（ｇ）を順次積層するように塗工する。得られた感熱記
録用材料を第５図に示す。第５図において、６は化合物
（Ａ）の層、７は発色剤の層、８は顕色剤の層である。(V) Coating liquid (f), coating liquid (e), and coating liquid (g) are sequentially layered on the support. The obtained thermosensitive recording material is shown in FIG. In FIG. 5, 6 is a layer of compound (A), 7 is a layer of color former, and 8 is a layer of color developer.
（Ｖｌ）支持体上に塗工液（ｂ）を塗工し、さらにその
上層に塗工液（ｃ）を塗工する。得られたｇ熱記録用材
料を第６図に示す。第６図において、３は化合物（Ａ）
と発色剤の混合した層、４は化合物（Ａ）と顕色剤の混
合した層である。(Vl) Coating liquid (b) is coated on the support, and coating liquid (c) is further coated on top of the coating liquid (b). The obtained g-thermal recording material is shown in FIG. In Figure 6, 3 is compound (A)
4 is a layer containing a mixture of compound (A) and a color developer, and 4 is a layer containing a mixture of compound (A) and a color developer.
（■）支持体上に塗工液（ｃ）を塗工し、さらにその上
層に塗工液（ｂ）を塗工する。得られた感熱記録用材料
を第７図に示す。第７図にわいて、４は化合物（Ａ）と
顕色剤の混合した層、３は化合物（Ａ）と発色剤の混合
した層である。(■) Coating liquid (c) is applied onto the support, and coating liquid (b) is further applied on top of the coating liquid (c). The obtained thermosensitive recording material is shown in FIG. In FIG. 7, 4 is a layer containing a mixture of compound (A) and a color developer, and 3 is a layer containing a mixture of compound (A) and a color former.
好ましい塗工方法および感熱記録用材料は（ＩＩ），（
■）および（■）である。Preferred coating methods and heat-sensitive recording materials are (II), (
■) and (■).
各層の塗工厚は感熱記録用材料．の形態およびその他の
条件により決定される。塗工量は特に限定されるもので
はないが、乾燥重量で通常０．５〜２０ｇ／ｗＰｓ
好ましくはｌ−１５ｇ／ｍ”、特に好ましくは３〜１０
ｇ／一である。The coating thickness of each layer is that of heat-sensitive recording material. Determined by the form and other conditions. The coating amount is not particularly limited, but is usually 0.5 to 20 g/wPs in terms of dry weight.
Preferably l-15 g/m", particularly preferably 3-10
g/one.
［実施例コ
以下、実施例により本発明をさらに説明するが、本発明
はこれに限定されるものではない。実施例中の部および
％は重■基準である。また実施例中の試験法を下記に示
す。[Example] The present invention will be further explained below with reference to Examples, but the present invention is not limited thereto. Parts and percentages in the examples are based on weight. Further, the test methods in the examples are shown below.
（試験法）
（１）発色性
感熱記録紙をＦｕｌｌ Ｍｏｄｅ Ａ−３ ７ｒａｎｓ
ｓｌｏｎ Ｆａｃｓｌｓ目ｅ ［（株）リコー製］の
試験機を用い発色させ、ＭｕｌｔＩ Ｓｐｅｃｔｒｏ
Ｃｏｌｏｕｒ ）ｌａｔｅｒ ＭＳＣ−２型 ［スガ機
械ｃ株）製コを用いて発色画像部の色濃度（Ｃ゜）を測
定した。この値は数値が大きい程発色濃度の高いことを
示す。(Test method) (1) Color-forming thermosensitive recording paper Full Mode A-3 7rans
Color was developed using a tester [manufactured by Ricoh Co., Ltd.], and Multi Spectro
The color density (C°) of the colored image area was measured using a MSC-2 model (manufactured by Suga Kikai Co., Ltd.). The larger the value, the higher the color density.
（２）白色度（地肌カプリ）
感熱記録紙の発色させる前のハンター白度、Ｂ値を上記
測定器で測定した。，この値は数値が大きい程白色度の
高いことを示す。(2) Whiteness (background capri) The Hunter whiteness and B value of the heat-sensitive recording paper before color development were measured using the above-mentioned measuring device. , This value indicates that the larger the value, the higher the degree of whiteness.
（３）耐湿性試験
発色性試験で発色させた画像部を４５゜Ｃ ，９０％Ｒ
ｌ｛の恒温恒湿槽中に２４時間放置後画像部の色濃度゜
（Ｃ・・）を測色した。(3) Moisture resistance test Color developed image area at 45°C, 90%R
After being left in a constant temperature and humidity bath for 24 hours, the color density of the image area (C...) was measured.
（４）耐可塑性試験
プラスチック消しゴムを発色性試験で発色させた画像部
の上にのせ２４時間放置後、画像部の色濃度（Ｃ゜）を
測色した。(4) Plasticity Resistance Test A plastic eraser was placed on the image area that had been colored in the color development test, and after being left for 24 hours, the color density (C°) of the image area was measured.
実施例１〜３、比較例１〜２
下記のＡ， ＢおよびＣ液をそれぞれポールミルにて
２４時間粉砕、分散した後、各液を充分混合し塗工液イ
〜へを作成した。この塗工液を上質紙（坪ｆｉ５０ｇ／
ｍ”）上に乾燥固形分量６ｇ／一となるようにドクター
ブレードで塗工し、乾燥後、感熱記録紙（実施例１〜３
）を作成した。Examples 1 to 3, Comparative Examples 1 to 2 The following liquids A, B, and C were respectively pulverized and dispersed in a Pall mill for 24 hours, and then each liquid was thoroughly mixed to prepare coating liquids A to I. Apply this coating liquid to high-quality paper (tsubo fi 50g/
m") using a doctor blade to give a dry solid content of 6 g/1, and after drying, heat-sensitive recording paper (Examples 1 to 3)
)It was created.
比較例１〜２として、Ａ液の本発明における化合物（Ａ
）の代わりに比較のための増感剤Ｈ−１（従来の化合物
）、Ｈ−２（従来の化合物）を用いて同様に行い、感熱
紙（比較例１〜２）を作成した。As Comparative Examples 1 and 2, the compound of the present invention (A
) The same procedure was carried out using sensitizers H-1 (conventional compound) and H-2 (conventional compound) for comparison to prepare thermal papers (Comparative Examples 1 and 2).
表−２ＣＡ液：増感剤の懸濁溶液コ
化合物（３）；
化合物（４）；
化合物（５）；
化合物（１）；
化合物（２）；
（部）
化合物（６〉；炭酸カルシウム
｛１物（７）； ヒドロキシエチルセルロース（５％
水溶液）
［Ｂ液：発色剤の懸濁溶液コ
３−（Ｎ−エチルＮ−ペンチルアミノ−６−メチル−７
−アニリノフルオラン［山田化学（株）製Ｓ−２０５１
＝１０部ヒドロキシエチルセ
ルロース ４０１１（（５％水溶液）
水
５０部［Ｃ液：顕色剤の＠濁溶液コ
ビスフェノールＡ ３０部炭酸カ
ルシウム １０部ポリビニルアル
コール
４０部
［記録紙の性能］
（５９Ａ水溶液）
水
２０部
表−３［塗工液コ
表−４
（部）
表−４から明らかなように本発明の感熱記録紙の発色性
は従来の感熱記録紙（比較例１、２）より著しくすぐれ
ていた。Table-2 CA solution: Suspension solution of sensitizer Compound (3); Compound (4); Compound (5); Compound (1); Compound (2); (Part) Compound (6>; Calcium carbonate {1) Material (7); Hydroxyethyl cellulose (5%
Aqueous solution) [Liquid B: Color former suspension solution 3-(N-ethyl N-pentylamino-6-methyl-7
-Anilinofluorane [S-2051 manufactured by Yamada Chemical Co., Ltd.
= 10 parts Hydroxyethylcellulose 4011 ((5% aqueous solution) Water
50 parts [Liquid C: Color developer @ cloudy solution Cobisphenol A 30 parts Calcium carbonate 10 parts Polyvinyl alcohol 40 parts [Performance of recording paper] (59A aqueous solution) Water 20 parts Table 3 [Coating liquid Table 4 (Part) As is clear from Table 4, the color development of the thermal recording paper of the present invention was significantly superior to that of the conventional thermal recording paper (Comparative Examples 1 and 2).
本発明の感熱記録紙の白色度（ハンター白度），耐湿性
および耐可塑剤性は従来の感熱記録紙（比較例１、２）
と比べすぐれていた。The whiteness (Hunter whiteness), moisture resistance, and plasticizer resistance of the thermal recording paper of the present invention were compared to that of conventional thermal recording paper (Comparative Examples 1 and 2).
It was superior compared to
実施例４〜６、比較例３
下記のＤ液およびＥ液をボールミルにて２４時間粉砕、
分故した後塗工液とした。この塗工液を上質紙（坪量Ｂ
ａｇ／ｍ２）に（Ｉ）、（ＶＩ）および（■）の方法、
すなわち（Ｉ）は紙にＤ液／Ｅ液の混合液（１／１重量
比）を乾燥固形分量８ｇ／一となるようにドクターブレ
ードにて塗工し乾燥した。（Ｖｌ）は紙に塗工液Ｄ液を
乾燥固形分量４ｇ／ｍｌとなるようにドクターブレード
にて塗工し、続いてこの層上に塗工液Ｅ液を同様に塗工
、乾燥した。（■）は（Ｖｌ）の逆で、先にＥ液を塗工
し、次いでＤ液を塗工した。塗工量は（Ｖｌ）と同じと
した。Examples 4 to 6, Comparative Example 3 The following solutions D and E were ground in a ball mill for 24 hours.
After separation, it was used as a coating liquid. Apply this coating liquid to high-quality paper (basis weight B
ag/m2) by methods (I), (VI) and (■),
Specifically, for (I), a mixed solution of liquid D/liquid E (1/1 weight ratio) was applied to paper using a doctor blade so that the dry solid content was 8 g/1, and then dried. For (Vl), Coating Liquid D was applied to paper using a doctor blade so that the dry solid content was 4 g/ml, and then Coating Liquid E was similarly applied onto this layer and dried. (■) is the opposite of (Vl), in which liquid E was applied first, and then liquid D was applied. The coating amount was the same as (Vl).
［Ｄ液：増感剤と発色剤の混合懸濁溶液］３−ジエチル
アミノー６−メチル７−アニリノフルオラン
３０部炭酸カルシウム
５部ポリビニルアルコール ３５部（５％
水溶液）
水
４０部
［Ｅ液：増感剤と顕色剤の混合懸濁液］ビスフェノール
Ａ ２０部ビス（４−ヒドロキシフ
ェニル）酢酸−ｎ−プチルエステル
１０部炭酸カルシウム
５部ポリビニルアルコール ３５部（５％水
溶液）
水 ２
５部塗工方法（Ｉ）、（ＶＩ）および（■）で作成した
感熱記録紙をそれぞれ実施例４〜６とした。[Liquid D: mixed suspension solution of sensitizer and color former] 3-diethylamino-6-methyl 7-anilinofluorane
30 parts calcium carbonate
5 parts Polyvinyl alcohol 35 parts (5%
Aqueous solution) 40 parts of water [Liquid E: mixed suspension of sensitizer and color developer] 20 parts of bisphenol A bis(4-hydroxyphenyl)acetic acid-n-butyl ester
10 parts calcium carbonate
5 parts Polyvinyl alcohol 35 parts (5% aqueous solution) Water 2
Thermal recording papers prepared by the 5-part coating methods (I), (VI) and (■) were designated as Examples 4 to 6, respectively.
また比較例３として、Ｄ液およびＥ液の本発明における
化合物（Ａ）の代わりにフタル酸ジフェニルエステルを
用いて（Ｉ）の塗工方法で塗工し感熱記録紙（比較例３
）を作成した。Further, as Comparative Example 3, phthalic acid diphenyl ester was used in place of the compound (A) in the present invention in Liquid D and Liquid E, and the thermal recording paper was coated by the coating method of (I) (Comparative Example 3).
)It was created.
５部
［記録紙の性能］
表−５
表−５から明らかなよつに本発明の感熱記録紙の白色度
、発色度、耐湿性および耐可塑剤性は、従来の感熱記録
紙（比較例４）よりすぐれていた。Part 5 [Performance of recording paper] Table 5 As is clear from Table 5, the whiteness, color development, moisture resistance, and plasticizer resistance of the thermal recording paper of the present invention are higher than that of the conventional thermal recording paper (comparative example). 4) It was better.
また、塗工方法において（Ｖｌ）の方法が感熱記録紙を
作る上で最もすぐれていた。Furthermore, among the coating methods, method (Vl) was the most excellent for producing thermal recording paper.
〔発明の効果］
本発明における化合物（Ａ）を含有する感熱記録用材料
は、従来のものに比べて著しく発色感度がよく、且つ白
色度（地肌カブリ）にすぐれている。[Effects of the Invention] The heat-sensitive recording material containing the compound (A) of the present invention has significantly better coloring sensitivity and whiteness (background fog) than conventional materials.
また、画像部は耐湿性、耐可塑剤性など高品位の堅牢度
を提供する。In addition, the image area provides high quality fastness such as moisture resistance and plasticizer resistance.
第１図〜第７図は本発明の感熱記録用材料の説明図（断
面図）である。
１・・・支持体、 ２・・・化合物（Ａ）と発色剤
と顕色剤の混合した層、 ３・・・化合物（Ａ）と発
色剤の混合した層、 ４・・・化合物（Ａ）と顕色剤
の混合した層、 ５・・・発色剤と顕色剤の混合した
層化合物（Ａ） ６・・・化合物（Ａ）の層、 ７・
・・発色剤の層、 ８・・・顕色剤の層
１
１ｌ
１ ｚ ｔ３
手続補正書
′ｇ３
口
１ ＋ １１
嘔 ５
口
′Ｓ も
図
１７
日
１．事件の表示
平成元年特許願第１５１３０４号
２．発明の名称
感熱記録用材料
３．補正をする者
事件との関係 特許出願人
住所 京都市東山区一橋野本町１１番地のｌ４．補正命
令の日付 自発
５．補正により増加する発明の数 ０６．補正の対
象
明細書の「図面の簡単な説明」の欄および図面
７．補正の内容
別紙の通り。図面については元の図面を別（１）明細書
第４０頁第８〜９行の「５・・・ 発色剤と顕色剤の混
合した層化合物（Ａ）」を「５・・・発色剤と顕色剤の
混合した層」に訂正する。
第１図
第２図
第３図FIGS. 1 to 7 are explanatory views (cross-sectional views) of the heat-sensitive recording material of the present invention. DESCRIPTION OF SYMBOLS 1... Support, 2... Layer containing a mixture of compound (A), a color former, and a color developer, 3... Layer containing a mixture of compound (A) and a color former, 4... Compound (A) ) and a color developer, 5... layer compound (A), a mixture of a color former and a color developer, 6... a layer of compound (A), 7.
...Layer of color former, 8...Layer of color developer 1 1l 1 z t3 Procedural amendment'g3 口1 + 11 小 5 口'S Also shown in Figure 17 Day 1. Display of the case 1989 Patent Application No. 151304 2. Name of the invention Thermosensitive recording material 3. Relationship with the case of the person making the amendment Patent applicant address: 14, 11 Hitotsubashino Honmachi, Higashiyama-ku, Kyoto City. Date of amendment order Voluntary5. Number of inventions increasing due to amendment 06. The “Brief Description of Drawings” column of the specification subject to amendment and Drawing 7. The details of the amendment are as shown in the attached sheet. Regarding the drawings, please refer to the original drawings separately. and a color developer." Figure 1 Figure 2 Figure 3
Claims (1)
化水素基、脂肪族モノカルボン酸残基または、−Ｒ＿３
（ＯＸ）＿■ＯＲ＿４［Ｒ＿３は脂肪族ジカルボン酸残
基または−ＣＨ＿２−であり、Ｒ＿４はフェノール類残
基；ただしＲ＿２が脂肪族炭化水素基または脂肪族モノ
カルボン酸残基の場合には、Ｒ＿１は−ＯＲ＿５基（Ｒ
＿５は炭素数６以下の炭化水素基である）、−ＮＯ＿２
基、−ＣＯＯＲ＿５基、−ＣＯＮＨＲ＿５基および−Ｃ
ＯＲ＿５基からなる群より選ばれる置換基を有したフェ
ノール類残基であり、Ｒ＿２が−Ｒ＿３（ＯＸ）＿■Ｏ
Ｒ＿４の場合はＲ＿１および／またはＲ＿４は−ＯＲ＿
５基、−ＮＯ＿２基、−ＣＯＯＲ５基、−ＣＯＮＨＲ＿
５基および−ＣＯＲ＿５基からなる群より選ばれる置換
基を有したフェノール類残基である］、Ｘは低級アルキ
レン基、ｍおよびｎは１〜３の整数である｝で表される
化合物（Ａ）を電子供与性無色発色剤と電子受容性顕色
性物質とを熱溶融させ発色させる原理に基づいた感熱記
録用材料上に含有させてなることを特徴とする感熱記録
用材料。 ２、Ｒ＿３の脂肪酸ジカルボン酸残基がシュウ酸残基ま
たはフマル酸残基である請求項１記載の材料。 ３、ｍおよびｎが１である請求項１または２記載の材料
。 ４、感熱記録用材料において支持体上に電子供与性無色
発色剤と電子受容性顕色性物質の混合した層、その上に
一般式（１）で表される化合物（Ａ）の層を積層してな
ることを特徴とする請求項１〜３のいずれか記載の材料
。 ５、感熱記録用材料において支持体上に一般式（１）で
表される化合物（Ａ）と電子供与性無色発色剤の混合し
た層、その上に該化合物（Ａ）と電子受容性顕色性物質
の混合した層を積層してなることを特徴とする請求項１
〜４のいずれか記載の材料。 ６、感熱記録用材料において支持体上に一般式（１）で
表される化合物（Ａ）と電子受容性顕色性物質の混合し
た層、その上に該化合物（Ａ）と電子供与性無色発色剤
の混合した層を積層してなることを特徴とする請求項１
〜５のいずれか記載の材料。[Claims] 1. General formula R_1-O-(XO)_■-R_2 (1) {In the formula, R_1 is a phenol residue, R_2 is an aliphatic hydrocarbon group, an aliphatic monocarboxylic acid residue Or -R_3
(OX)_■OR_4 [R_3 is an aliphatic dicarboxylic acid residue or -CH_2-, R_4 is a phenol residue; However, if R_2 is an aliphatic hydrocarbon group or an aliphatic monocarboxylic acid residue, R_1 is -OR_5 group (R
_5 is a hydrocarbon group having 6 or less carbon atoms), -NO_2
group, -COOR_5 group, -CONHR_5 group and -C
It is a phenolic residue having a substituent selected from the group consisting of OR_5 groups, and R_2 is -R_3(OX)_■O
If R_4 then R_1 and/or R_4 is -OR_
5 groups, -NO_2 groups, -COOR5 groups, -CONHR_
5 groups and -COR_5 groups], X is a lower alkylene group, m and n are integers from 1 to 3} ) on a heat-sensitive recording material based on the principle of heat-melting an electron-donating colorless coloring agent and an electron-accepting color-developing substance to develop color. 2. The material according to claim 1, wherein the fatty acid dicarboxylic acid residue of R_3 is an oxalic acid residue or a fumaric acid residue. 3. The material according to claim 1 or 2, wherein m and n are 1. 4. In a heat-sensitive recording material, a layer containing a mixture of an electron-donating colorless color former and an electron-accepting color developing substance is laminated on a support, and a layer of a compound (A) represented by general formula (1) is laminated thereon. The material according to any one of claims 1 to 3, characterized in that it is made of: 5. In a heat-sensitive recording material, a layer containing a mixture of the compound (A) represented by the general formula (1) and an electron-donating colorless coloring agent on a support, and a layer containing the compound (A) and an electron-accepting color developer thereon. Claim 1 characterized in that it is formed by laminating layers in which a sexual substance is mixed.
4. The material according to any one of items 4 to 4. 6. In a heat-sensitive recording material, a layer containing a mixture of the compound (A) represented by the general formula (1) and an electron-accepting color developing substance on a support, and a layer containing the compound (A) and an electron-donating colorless substance on the support. Claim 1 characterized in that it is formed by laminating layers in which a coloring agent is mixed.
5. The material according to any one of items 5 to 5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1151304A JPH0316781A (en) | 1989-06-14 | 1989-06-14 | Material for thermal recording |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1151304A JPH0316781A (en) | 1989-06-14 | 1989-06-14 | Material for thermal recording |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0316781A true JPH0316781A (en) | 1991-01-24 |
Family
ID=15515745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1151304A Pending JPH0316781A (en) | 1989-06-14 | 1989-06-14 | Material for thermal recording |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0316781A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10899698B2 (en) | 2010-10-26 | 2021-01-26 | Ethox Chemicals, Llc | Bis(aryloxyalkyl) esters of aromatic polycarboxylic acids and method of preparation |
-
1989
- 1989-06-14 JP JP1151304A patent/JPH0316781A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10899698B2 (en) | 2010-10-26 | 2021-01-26 | Ethox Chemicals, Llc | Bis(aryloxyalkyl) esters of aromatic polycarboxylic acids and method of preparation |
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