JPH04219280A - Sensitizer for thermal recording and thermal recording material - Google Patents
Sensitizer for thermal recording and thermal recording materialInfo
- Publication number
- JPH04219280A JPH04219280A JP2226360A JP22636090A JPH04219280A JP H04219280 A JPH04219280 A JP H04219280A JP 2226360 A JP2226360 A JP 2226360A JP 22636090 A JP22636090 A JP 22636090A JP H04219280 A JPH04219280 A JP H04219280A
- Authority
- JP
- Japan
- Prior art keywords
- sensitizer
- acid
- layer
- heat
- 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 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 12
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical group SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims abstract description 12
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 7
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 7
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 239000003086 colorant Substances 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N fumaric acid group Chemical group C(\C=C\C(=O)O)(=O)O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 6
- 125000001142 dicarboxylic acid group Chemical group 0.000 claims description 3
- -1 dimethyl terephthalate compound Chemical class 0.000 abstract description 74
- 230000035945 sensitivity Effects 0.000 abstract description 13
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 9
- 239000000194 fatty acid Substances 0.000 abstract description 9
- 229930195729 fatty acid Natural products 0.000 abstract description 9
- 150000004665 fatty acids Chemical class 0.000 abstract description 9
- 239000004014 plasticizer Substances 0.000 abstract description 7
- 150000003839 salts Chemical class 0.000 abstract description 7
- 229910052751 metal Inorganic materials 0.000 abstract description 6
- 239000002184 metal Substances 0.000 abstract description 6
- 239000000314 lubricant Substances 0.000 abstract description 5
- 206010034972 Photosensitivity reaction Diseases 0.000 abstract 1
- 230000036211 photosensitivity Effects 0.000 abstract 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 abstract 1
- 238000000576 coating method Methods 0.000 description 40
- 239000011248 coating agent Substances 0.000 description 35
- 239000007788 liquid Substances 0.000 description 32
- 239000000243 solution Substances 0.000 description 18
- 239000002253 acid Substances 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 239000000725 suspension Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 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 9
- 239000000126 substance Substances 0.000 description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 150000001991 dicarboxylic acids Chemical class 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000005690 diesters Chemical class 0.000 description 6
- 229930185605 Bisphenol Natural products 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 5
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000011981 development test Methods 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000010298 pulverizing process Methods 0.000 description 4
- 239000008117 stearic acid 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
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 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
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- KZTYYGOKRVBIMI-UHFFFAOYSA-N S-phenyl benzenesulfonothioate Natural products C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 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
- 150000001350 alkyl halides Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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
- SCBGJZIOPNAEMH-UHFFFAOYSA-N 2,2-bis(4-hydroxyphenyl)acetic acid Chemical compound C=1C=C(O)C=CC=1C(C(=O)O)C1=CC=C(O)C=C1 SCBGJZIOPNAEMH-UHFFFAOYSA-N 0.000 description 2
- ZVLOLTTVYNWVHH-UHFFFAOYSA-N 2-[1-(2-hydroxyphenyl)-1-phenylethyl]phenol Chemical compound C=1C=CC=C(O)C=1C(C=1C(=CC=CC=1)O)(C)C1=CC=CC=C1 ZVLOLTTVYNWVHH-UHFFFAOYSA-N 0.000 description 2
- JLDOPTPEFOPANL-UHFFFAOYSA-N 2-cyclohexyl-4-[1-(5-cyclohexyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C2CCCCC2)=C(O)C=C(C)C=1C(CCC)C(C(=CC=1O)C)=CC=1C1CCCCC1 JLDOPTPEFOPANL-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
- XJMMNTGIMDZPMU-UHFFFAOYSA-N 3-methylglutaric acid Chemical compound OC(=O)CC(C)CC(O)=O XJMMNTGIMDZPMU-UHFFFAOYSA-N 0.000 description 2
- MTMKZABGIQJAEX-UHFFFAOYSA-N 4,4'-sulfonylbis[2-(prop-2-en-1-yl)phenol] Chemical compound C1=C(CC=C)C(O)=CC=C1S(=O)(=O)C1=CC=C(O)C(CC=C)=C1 MTMKZABGIQJAEX-UHFFFAOYSA-N 0.000 description 2
- ZTILAOCGFRDHBH-UHFFFAOYSA-N 4-(4-propan-2-yloxyphenyl)sulfonylphenol Chemical compound C1=CC(OC(C)C)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 ZTILAOCGFRDHBH-UHFFFAOYSA-N 0.000 description 2
- 229940090248 4-hydroxybenzoic acid Drugs 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
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- JPIYZTWMUGTEHX-UHFFFAOYSA-N auramine O free base Chemical compound C1=CC(N(C)C)=CC=C1C(=N)C1=CC=C(N(C)C)C=C1 JPIYZTWMUGTEHX-UHFFFAOYSA-N 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
- 235000010290 biphenyl Nutrition 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 125000002704 decyl group Chemical group [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])* 0.000 description 2
- JJXVDRYFBGDXOU-UHFFFAOYSA-N dimethyl 4-hydroxybenzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC=C(O)C=C1C(=O)OC JJXVDRYFBGDXOU-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-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
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-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
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000005419 hydroxybenzoic acid derivatives Chemical class 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
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 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
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 2
- 150000005209 naphthoic acids Chemical class 0.000 description 2
- 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 2
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- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
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- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
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- 238000010998 test method Methods 0.000 description 2
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 150000003751 zinc Chemical class 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 1
- 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
- XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 description 1
- GRUKYNOFYJVELY-UHFFFAOYSA-N 1,3-bis[(4-hydroxyphenyl)sulfanyl]propan-2-one Chemical compound C1=CC(O)=CC=C1SCC(=O)CSC1=CC=C(O)C=C1 GRUKYNOFYJVELY-UHFFFAOYSA-N 0.000 description 1
- RUTJJFYMKNSTIA-UHFFFAOYSA-N 1,3-thiazole-2,4-dicarboxylic acid Chemical compound OC(=O)C1=CSC(C(O)=O)=N1 RUTJJFYMKNSTIA-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
- 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
- RBYXVXBZHQRMHJ-UHFFFAOYSA-N 1-docosyl-3-octadecylurea Chemical compound CCCCCCCCCCCCCCCCCCCCCCNC(=O)NCCCCCCCCCCCCCCCCCC RBYXVXBZHQRMHJ-UHFFFAOYSA-N 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 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
- 238000003825 pressing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000004576 sand Substances 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
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-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
- 230000003068 static effect Effects 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 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
- 229920001897 terpolymer Polymers 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 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
- QODCFQHJGUTALY-UHFFFAOYSA-L zinc;1h-indole-2-carboxylate Chemical compound [Zn+2].C1=CC=C2NC(C(=O)[O-])=CC2=C1.C1=CC=C2NC(C(=O)[O-])=CC2=C1 QODCFQHJGUTALY-UHFFFAOYSA-L 0.000 description 1
- JFTNAXDYYMQUHC-UHFFFAOYSA-L zinc;4-nitrobenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=C([N+]([O-])=O)C=C1.[O-]C(=O)C1=CC=C([N+]([O-])=O)C=C1 JFTNAXDYYMQUHC-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]
本発明は感熱記録用増感剤および感熱記録用材料に関す
る。さらに詳しくは感熱記録紙用などの増感剤および感
熱記録紙などの感熱記録用材料に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a heat-sensitive recording sensitizer and a heat-sensitive recording material. More specifically, the present invention relates to a sensitizer for heat-sensitive recording paper and a heat-sensitive recording material such as heat-sensitive recording paper.
[従来の技術]
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が
求められている。感熱記録紙などの感熱記録用材料は紙
などの支持体上に形成される層に含まれる電子供与性無
色発色剤と電子受容性顕色性物質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
。[Prior Art] In recent years, there has been a significant demand for faster information processing, and various high-speed devices have been developed. Along with this, there is a demand for highly sensitive heat-sensitive recording materials. Heat-sensitive recording materials such as heat-sensitive recording paper develop color by melting an electron-donating colorless coloring agent and an electron-accepting color-developing substance contained in a layer formed on a support such as paper with heat and causing the two to associate. It is made using the principle of
上記発色剤、顕色性物質に併用して感度向上を図るため
の増感剤として、従来たとえば、フタル酸ジフェニルエ
ステル(特開昭57−116690号公報)、ベンジル
ビフェニル類(特開昭60−82382号公報)、β,
β’−ビス−P−メトキシフェノキシエチルエーテルと
1,4−ビスβ,β’フェノキシエトキシベンゼンとの
混合物(特開昭64−31680号公報)および、テレ
フタル酸とモノオキシエチレンメチルフェニルエーテル
とのジエステル(特開平2−6180号公報)などが提
案されている。Conventional sensitizers used in combination with the above color forming agents and color developing substances to improve sensitivity include phthalic acid diphenyl ester (Japanese Unexamined Patent Publication No. 57-116690), benzyl biphenyls (Japanese Unexamined Patent Publication No. 116690/1983), 82382), β,
A mixture of β'-bis-P-methoxyphenoxyethyl ether and 1,4-bisβ,β'phenoxyethoxybenzene (JP-A-64-31680) and a mixture of terephthalic acid and monooxyethylene methylphenyl ether. Diesters (Japanese Unexamined Patent Publication No. 2-6180) and the like have been proposed.
[発明が解決しようとする課題]
しかし、これら増感剤を用いた感熱記録用材料ではまだ
発色感度が不十分で、とくにスティッキング防止のため
にステアリン酸亜鉛、ステアリン酸カルシウムなどの高
級脂肪酸金属塩などの滑剤を通常、添加されるが、その
場合発色感度が低下する。また感度アップによる副作用
、すなわち白色度、耐光性、耐湿性および耐可塑剤性の
低下を免れないという問題があつた。[Problems to be solved by the invention] However, the color development sensitivity of heat-sensitive recording materials using these sensitizers is still insufficient, and in particular higher fatty acid metal salts such as zinc stearate and calcium stearate are used to prevent sticking. Usually, a lubricant is added, but in this case, color development sensitivity decreases. In addition, there was a problem in that side effects due to increased sensitivity, namely, reductions in whiteness, light resistance, moisture resistance, and plasticizer resistance, were unavoidable.
[課題を解決するための手段]
本発明者らは、これらの問題を解決すべく鋭意検討した
結果本発明に到達した。すなわち、本発明はテレフタル
酸ジメチルエステル(A)、一般式
{式中、R1は置換基を有していてもよい(チオ)フェ
ノール類残基、Xは炭素数1〜4のアルキレン基、Yは
OまたはS原子、R2は脂肪族炭化水素基、脂肪族モノ
カルボン酸残基または式[式中、R3はジカルボン酸残
基または−CH2−、R4は置換基を有していてもよい
(チオ)フェノール類残基、Xは1〜4のアルキレン基
、YはOまたはS原子、nは1〜3の整数を表す。]で
示される基、mは1〜3の整数を表す。}で示される化
合物(B)、および必要により一般式
[式中、R5およびR6は置換基を有していてもよいフ
ェノール類残基、YはOまたはS原子を表す。[Means for Solving the Problems] The present inventors have arrived at the present invention as a result of intensive studies to solve these problems. That is, the present invention provides terephthalic acid dimethyl ester (A), general formula {wherein R1 is a (thio)phenol residue which may have a substituent, X is an alkylene group having 1 to 4 carbon atoms, Y is an O or S atom, R2 is an aliphatic hydrocarbon group, an aliphatic monocarboxylic acid residue or a formula [wherein R3 is a dicarboxylic acid residue or -CH2-, R4 may have a substituent] thio)phenol residue, X represents an alkylene group of 1 to 4, Y represents an O or S atom, and n represents an integer of 1 to 3. ], m represents an integer of 1 to 3. }, and optionally the general formula [wherein R5 and R6 are phenol residues which may have substituents, and Y represents an O or S atom.
]で示される化合物(C)からなることを特徴とする感
熱記録用増感剤;および支持体上に形成される層に少な
くとも電子供与性無色発色剤と電子受容性顕色性物質を
含有し、且つ熱により発色する感熱記録用材料において
上記増感剤を支持体上に形成される層に含有することを
特徴とする感熱記録用材料である。A sensitizer for heat-sensitive recording characterized by comprising the compound (C) represented by , and a heat-sensitive recording material which develops color by heat, characterized in that the above-mentioned sensitizer is contained in a layer formed on a support.
本発明において、残基とはある化合物から−OH基また
は−SH基を除いた基を意味する。In the present invention, a residue means a group obtained by removing an -OH group or a -SH group from a certain compound.
一般式(1)において、R1およびR4で示される基の
うち置換基を有していてもよい(チオ)フェノール類残
基を構成する(チオ)フェノール類としては、たとえば
(チオ)フェノール、置換基を有する(チオ)フェノー
ル、(チオ)ナフトール、置換基を有する(チオ)ナフ
トールなどがあげられる。また上記の置換基の具体例と
しては、アルキル基[メチル、エチル、n−ブチル、t
ert−ブチル、ヘキシル、オクチル、ノニル、デシル
、ジメチル、ジノニル基など]、アルケニル基[イソプ
ロペニル、アリル基など]、アラルキル基[ベンジル、
フェネチル基など]、アリール基[フェニル、トリル、
キシリル、ビフェニル、ナフチル、クミル基など]、シ
クロアルキル基[シクロヘキシル基など]、アルコキシ
基[メトキシ、エトキシ基など]、アリーロキシ基[フ
ェノキシ基など]、アルキルチオ基[メチルチオ、エチ
ルチオ基など]、アリールチオ基[フェニルチオ基など
]、アルコキシカルボニル基[メトキシカルボニル、エ
トキシカルボニル、tert−ブトキシカルボニル基な
ど]、アリーロキシカルボニル基[フェノキシカルボニ
ル基など]、アシル基[アセチル、プロピオニル、ブチ
リル、イソブチリル基など]、アリーロイル基[ベンゾ
イル基など]、ハロゲン基[クロル、ブロム基など]、
シアノ基、ニトロ基などがあげられる。R1およびR4
は同一でも、異なつていてもよい。In general formula (1), among the groups represented by R1 and R4, the (thio)phenols constituting the (thio)phenol residue which may have a substituent include, for example, (thio)phenol, substituted Examples include (thio)phenol having a group, (thio)naphthol, and (thio)naphthol having a substituent. Specific examples of the above substituents include alkyl groups [methyl, ethyl, n-butyl, t
ert-butyl, hexyl, octyl, nonyl, decyl, dimethyl, dinonyl group, etc.], alkenyl group [isopropenyl, allyl group, etc.], aralkyl group [benzyl,
phenethyl group], aryl group [phenyl, tolyl,
xylyl, biphenyl, naphthyl, cumyl group, etc.], cycloalkyl group [cyclohexyl group, etc.], alkoxy group [methoxy, ethoxy group, etc.], aryloxy group [phenoxy group, etc.], alkylthio group [methylthio, ethylthio group, etc.], arylthio group [Phenylthio group, etc.], alkoxycarbonyl group [methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl group, etc.], aryloxycarbonyl group [phenoxycarbonyl group, etc.], acyl group [acetyl, propionyl, butyryl, isobutyryl group, etc.], aryloyl group groups [such as benzoyl groups], halogen groups [chloro, bromo groups, etc.],
Examples include cyano group and nitro group. R1 and R4
may be the same or different.
本発明においてR2を示す基のうち脂肪族炭化水素基と
しては、炭素数が通常1〜18の直鎖または分岐のアル
キル基、および炭素数が通常2〜22のアルケニル基が
あげられる。アルキル基の具体例としては、メチル、エ
チル、プロピル、ブチル、ヘキシル、ヘプチル、オクチ
ル、イソオクチル、デシル、ドデシル、ペンタデシル、
ヘキサデシル基などが、またアルケニル基の具体例とし
てはドデセニル、オクタデセニル基などがあげられる。Among the groups representing R2 in the present invention, examples of aliphatic hydrocarbon groups include linear or branched alkyl groups, which usually have 1 to 18 carbon atoms, and alkenyl groups, which usually have 2 to 22 carbon atoms. Specific examples of alkyl groups include methyl, ethyl, propyl, butyl, hexyl, heptyl, octyl, isooctyl, decyl, dodecyl, pentadecyl,
Examples of the alkenyl group include hexadecyl group, and dodecenyl and octadecenyl groups.
R2を示す基のうち、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1〜
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があげられる。この具体
例としては、ギ酸、酢酸、プロピオン酸、カプロン酸、
カプリン酸、ラウリン酸、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;並び
に牛脂脂肪酸、パーム油脂肪酸、大豆油脂肪酸などの天
然油脂より得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、炭素数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。Among the groups representing R2, the aliphatic monocarboxylic acids constituting the aliphatic monocarboxylic acid residues usually have 1 to 1 carbon atoms.
30, preferably 8 to 20 linear or branched saturated or unsaturated aliphatic monocarboxylic acids. Specific examples include formic acid, acetic acid, propionic acid, caproic acid,
Saturated aliphatic monocarboxylic acids such as capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, erucic acid; oleic acid, linoleic acid,
Examples include unsaturated aliphatic monocarboxylic acids such as linoleic acid; and aliphatic monocarboxylic acids obtained from natural oils and fats such as beef tallow fatty acid, palm oil fatty acid, and soybean oil fatty acid. Among these, preferred are saturated or unsaturated monocarboxylic acids having 8 to 20 carbon atoms, and particularly preferred is stearic acid.
R3を示す基のうちジカルボン酸残基を構成するジカル
ボン酸としては炭素数2〜18のジカルボン酸があげら
れる。この具体例としては、シュウ酸、マロン酸、(無
水)コハク酸、グルタル酸、アジピン酸などの脂肪族ジ
カルボン酸(酸無水物も含む)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
互換ジカルボン酸;ハロゲノマロン酸、ハロゲノコハク
酸、トリブロムコハク酸などのハロゲノジカルボン酸;
(無水)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−ム
コン酸、カロチノイド、アセチレンジカルボン酸などの
脂肪族不飽和ジカルボン酸;(無水)フタル酸、テレフ
タル酸などの芳香族ジカルボン酸(酸無本物も含む);
シクロプロパン−1,1−ジカルボン酸,1−メチル−
1,2−ペンタンジカルボン酸、1,1−シクロヘキサ
ンジカルボン酸、1,3−シクロヘキサンジエン−1,
2−ジカルボン酸などの脂環式ジカルボン酸;フラン−
2,3−ジカルボン酸、フラン−2,5−ジメチル−3
,4−ジカルボン酸,3−メチルインドール−2,5−
ジカルボン酸、2,4−チアゾールジカルボン酸、4,
5−イミダゾールジカルボン酸などのヘテロ原子を含む
ジカルボン酸(酸無水物も含む);並びにこれらジカル
ボン酸とメチル、エチル、プロピ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。Among the groups representing R3, dicarboxylic acids constituting the dicarboxylic acid residue include dicarboxylic acids having 2 to 18 carbon atoms. Specific examples include aliphatic dicarboxylic acids (including acid anhydrides) such as oxalic acid, malonic acid, succinic acid (anhydride), glutaric acid, adipic acid, methylsuccinic acid, α-methylglutaric acid, β-methylglutaric acid. Alkyl-compatible dicarboxylic acids such as; halogenodicarboxylic acids such as halogenomalonic acid, halogenosuccinic acid, tribromosuccinic acid;
(Anhydrous) Aliphatic unsaturated dicarboxylic acids such as maleic acid, fumaric acid, itaconic acid, citraconic acid, mesaconic acid, glutaconic acid, muconic acid, cis-muconic acid, carotenoids, acetylene dicarboxylic acid; (Anhydrous) phthalic acid, terephthalic acid Aromatic dicarboxylic acids such as acids (including non-acidic acids);
Cyclopropane-1,1-dicarboxylic acid, 1-methyl-
1,2-pentanedicarboxylic acid, 1,1-cyclohexanedicarboxylic acid, 1,3-cyclohexanediene-1,
Alicyclic dicarboxylic acids such as 2-dicarboxylic acids; furan-
2,3-dicarboxylic acid, furan-2,5-dimethyl-3
,4-dicarboxylic acid,3-methylindole-2,5-
dicarboxylic acid, 2,4-thiazoledicarboxylic acid, 4,
Examples include dicarboxylic acids (including acid anhydrides) containing heteroatoms such as 5-imidazoledicarboxylic acid; and esters of these dicarboxylic acids and lower alcohols such as methyl, ethyl, and propyl alcohol.
これらのうち好ましいものは、シュウ酸、マロン酸、無
水コハク酸、無水マレイン酸、フマル酸および無水フタ
ル酸である。またR3を示す基としては、−CH2−も
好ましい。Preferred among these are oxalic acid, malonic acid, succinic anhydride, maleic anhydride, fumaric acid and phthalic anhydride. Also preferred as the group representing R3 is -CH2-.
本発明において、Xを示す炭素数1〜4のアルキレン基
としては、たとえば、メチレン、エチレン、プロピレン
およびブチレン基、好ましくはメチレンおよびエチレン
基があげられる。また、mおよびnは好ましくは1であ
る。In the present invention, examples of the C1-C4 alkylene group represented by X include methylene, ethylene, propylene and butylene groups, preferably methylene and ethylene groups. Further, m and n are preferably 1.
該一般式(1)で示される化合物(B)の具体例を下記
の通り[1]〜[10]に示す。Specific examples of the compound (B) represented by the general formula (1) are shown in [1] to [10] below.
[なお、置換基を有していてもよい(チオ)フェノール
類(フェノール、ナフトールを含む)はフェノール類お
よびチオフェノール類と略記した。][1](ポリ)ア
ルキレングリコールフェニル類エーテルとアルキルハラ
イドとのエーテル[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
ルと芳香族ジカルボン酸とのジエステル
など
[4](ポリ)アルキレングリコールフェニル類エーテ
ルと脂肪族ジカルボン酸とのジエステル
など
[5](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
[6](ポリ)アルキレングリコールチオフェニル類エ
ーテルとアルキルハライドとのエーテル
[7](ポリ)アルキレングリコールチオフェニル類エ
ーテルと脂肪族モノカルボン酸とのモノエステル
など
[8](ポリ)アルキレングリコールチオフェニル類エ
ーテルと芳香族ジカルボン酸とのジエステル
など
[9](ポリ)アルキレングリコールチオフェニル類エ
ーテルと脂肪族ジカルボン酸とのジエステル
など
[10](ポリ)アルキレングリコールチオフェニル類
エーテルとホルマリンとのジアセタール
など
以上例示した化合物(B)のうち好ましいものは、[1
]、[3]、[4]および[5]で例示した各化合物で
あり、特に好ましいのは、エチレングリコールフェニル
類エーテルとフタル酸とのジエステル、エチレングリコ
ールフェニル類エーテルとシュウ酸とのジエステルおよ
びエチレングリコールフェニル類エーテルとフマル酸と
のジエステルである。[Note that (thio)phenols (including phenol and naphthol) that may have substituents are abbreviated as phenols and thiophenols. ] [1] Ether of (poly)alkylene glycol phenyl ether and alkyl halide [2] Monoester of (poly)alkylene glycol phenyl ether and aliphatic monocarboxylic acid [3] (poly)alkylene glycol phenyl ether and aromatic dicarboxylic acids, etc. [4] Diesters of (poly)alkylene glycol phenyl ethers and aliphatic dicarboxylic acids, etc. [5] Diacetals of (poly)alkylene glycol phenyl ethers and formalin, etc. [6] ( Ethers of poly)alkylene glycol thiophenyl ethers and alkyl halides [7] Monoesters of (poly)alkylene glycol thiophenyl ethers and aliphatic monocarboxylic acids, etc. [8] (Poly)alkylene glycol thiophenyl ethers Diesters with aromatic dicarboxylic acids, etc. [9] Diesters between (poly)alkylene glycol thiophenyl ethers and aliphatic dicarboxylic acids, etc. [10] Diacetals between (poly)alkylene glycol thiophenyl ethers and formalin, etc. Preferable compounds among compounds (B) are [1
], [3], [4] and [5], particularly preferred are diesters of ethylene glycol phenyl ether and phthalic acid, diesters of ethylene glycol phenyl ether and oxalic acid, and It is a diester of ethylene glycol phenyl ether and fumaric acid.
化合物(B)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 (B) may be used in combination.
一般式(1)で表される化合物(B)は、任意の方法で
製造することができ、この製法を例示すると該置換基を
有していてもよいフェノール類に炭素数1〜4のアルキ
レンオキサイドを付加させ[(XO)m、(OX)G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
。上記の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、メチラー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。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。The compound (B) represented by the general formula (1) can be produced by any method. To illustrate this production method, the phenol which may have a substituent is added to an alkylene having 1 to 4 carbon atoms. It can be obtained by adding an oxide [constituting (XO)m, (OX)G], then reacting with a dicarboxylic acid (constituting R2), and diesterifying it. The above-mentioned method for adding the alkylene oxide is a known method, for example, using an alkaline catalyst such as caustic soda, caustic potash, metallic sodium, or methylate, under pressure,
This can be carried out by adding at 160 to 190°C. The number of moles of alkylene oxide added is m and n
can be arbitrarily changed within the range of 1 to 3.
上記ジカルボン酸類の反応は通常の方法、たとえば硫酸
、P−トルエンスルホン酸、リン酸などの酸性触媒また
は苛性ソーダ、苛性カリなどのアルカリ性触媒の存在下
、常圧または減圧下、150〜250℃で反応を行うこ
とができる。The reaction of the dicarboxylic acids mentioned above is carried out in a conventional manner, for example, in the presence of an acidic catalyst such as sulfuric acid, P-toluenesulfonic acid, or phosphoric acid, or an alkaline catalyst such as caustic soda or caustic potash, under normal pressure or reduced pressure, at 150 to 250°C. It can be carried out.
一般式(2)において、R5およびR6の一般式(1)
のR1、R4として例示したものと同じでよい。また、
R5およびR6は同一でも異なつていてもよい。R5Y
CH2−基およびR6YCH2−基相互のフェノール環
への結合の位置は、o、m、p位のいずれでもよくp位
が好ましい。In general formula (2), R5 and R6 have general formula (1)
They may be the same as those exemplified as R1 and R4. Also,
R5 and R6 may be the same or different. R5Y
The bonding position between the CH2- group and the R6YCH2- group to the phenol ring may be any of the o, m, and p positions, with the p position being preferred.
一般式(2)で示される化合物(C)の具体例を示せば
下記[1]および[2]に示す。Specific examples of the compound (C) represented by the general formula (2) are shown in [1] and [2] below.
[1]置換基を有していてもよいフェノール類とP−キ
シレンハライドとのジエーテル
など
[2]置換基を有していてもよいチオフェノール類とキ
シレンハライドとのジエーテル
など
以上例示した化合物(C)のうち好ましいものは、[1
]で例示した化合物であり、特に好ましいものはフェノ
ールとP−キシレンハライドとのジエーテル、メチルフ
ェノールとP−キシレンハライドとのジエーテル、およ
びメトキシフェノールとP−キシレンハライドとのジエ
ーテルである。[1] Dieters of phenols that may have substituents and P-xylene halide, etc. [2] Dieters of thiophenols that may have substituents and xylene halide, etc. Compounds exemplified above ( Among C), preferred are [1
Of the compounds exemplified above, particularly preferred are diethers of phenol and P-xylene halide, diethers of methylphenol and P-xylene halide, and diethers of methoxyphenol and P-xylene halide.
化合物(C)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 (C) may be used in combination.
本発明において該電子供与性無色発色剤(以下発色剤と
略記)としては、特に限定はなく、たとえば公知の感熱
または感圧記録材料に使用されているものがあげられる
。この公知の発色剤としては、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、スピロピラン系などの発色剤があげられる
。In the present invention, the electron-donating colorless coloring agent (hereinafter abbreviated as coloring agent) is not particularly limited, and includes, for example, those used in known heat-sensitive or pressure-sensitive recording materials. Examples of the known coloring agents include triarylmethane-based, diphenylmethane-based, xanthene-based, phenothiazine-based, and spiropyran-based coloring agents.
トリアリールメタン系発色剤の具体例としては、3.3
−ビス(p−ジメチルアミノフェニル)−6−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)、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)−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−フエニルイン
ドール−3−イル)フタリド,3.3−ビス(1.2−
ジメチルインドール−3−イル)−5−ジメチルアミノ
フタリド、3.3−ビス−(1.2−ジメチルインドー
ル−3−イル)−6−ジメチルアミノフタリド、3.3
−ビス(9−エチルカルバゾール−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)−5−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−メチルピ
ロール−2−イル)−6−ジメチルアミノフタリドなど
があげられる。Specific examples of triarylmethane color formers include 3.3
-Bis(p-dimethylaminophenyl)-6-dimethylaminophthalide (crystal violet lactone, hereinafter abbreviated as CVL), 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-phenylindol-3-yl)phthalide, 3.3-bis(1.2-
dimethylindol-3-yl)-5-dimethylaminophthalide, 3.3-bis-(1.2-dimethylindol-3-yl)-6-dimethylaminophthalide, 3.3
-bis(9-ethylcarbazol-3-yl)-5-dimethylaminophthalide, 3.3-bis(2-phenylindol-3-yl)-5-dimethylaminophthalide,
Examples include 3-p-dimethylaminophenyl-3-(1-methylpyrrol-2-yl)-6-dimethylaminophthalide.
ジフェニルメタン系発色剤としては、4・4’−ビス−
ジメチルアミノベ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。As a diphenylmethane color former, 4,4'-bis-
Dimethylaminobenzhydrin benzyl ether, N-
Examples include halophenyl leuco auramine and N-2.4.5-trichlorophenyl leuco auramine.
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(p−ニトロアニリノ)ラクタ
ム、ローダミン(O−クロロアニリノ)ラクタム、3−
ジエチルアミノ−7,8−ベンゾフルオラン、ローダミ
ン−B−(P−クロロアニリノラクタム)、2−アニリ
ノ−3−メチル−6−ジメチルアミノフルオラン、2−
アニリノ−3−メチル−6−N−エチルアミノフルオラ
ン、2−アニリノ−3−メチル−6−N−メチル−N−
(イソプロピル)アミノフルオラン、2−アニリノ−3
−メチル−6−N−メチル−N−シクロヘキシルアミノ
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−ジ
ブチルアミノフルオラン、2−アニリノ−3−クロロ−
6−ジメ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−イソアミルアミノフルオラ
ン、2−アニリノ−3−クロロ−6−ジエチルアミノフ
ルオラン、2−アニリノ−3−クロロ−6−N−メチル
−N−エチルアミノフルオラン、2−アニリノ−3−ク
ロロ−6−N−メチル−N−(イソプロピル)アミノフ
ルオラン、2−アニリノ−3−クロロ−6−N−メチル
−N−シクロヘキシルアミノフルオラン、2−アニリノ
−3−クロロ−6−N−メチル−N−ペンチルアミノフ
ルオラン、2−(P−メチルアニリノ)−3−メチル−
6−ジメチルアミノフルオラン、2−(P−メチルアニ
リノ)−3−メチル−6−N−メチル−N−エチルアミ
ノフルオラン、2−(P−メチルアニリノ)−3−メチ
ル−6−N−メチル−N−(イソプロピル)アミノフル
オラン、2−(P−メチルアニリノ)−3−メチル−6
−N−メチル−N−ペンチルアミノフルオラン、2−(
P−メチルアニリノ)−3−メチル−6−N−メチル−
N−シクロヘキシルアミノフルオラン、2−(P−メチ
ルアニリノ)−3−メチル−6−N−エチル−N−ペン
チルアミノフルオラン、2−(P−メチルアニリノ)−
3−クロロ−6−ジメチルアミノフルオラン、2−(P
−メチルアニリノ)−3−クロロ−6−ジエチルアミノ
フルオラン、2−(P−メチルアニリノ)−3−クロロ
−6−N−メチル−N−エチルアミノフルオラン、2−
(P−メチルアニリノ)−3−クロロ−6−N−メチル
−N−(イソプロピル)アミノフルオラン、2−(P−
メチルアニリノ)−3−クロロ−6−N−メチル−N−
シクロヘキシルアミノフルオラン、2−(P−メチルア
ニリノ)−3−クロロ−6−N−メチル−N−ペンチル
アミノフルオラン、2−(P−メチルアニリノ)−3−
クロロ−6−N−エチル−N−ペンチルアミノフルオラ
ン、2−(P−メチルアニリノ)−3−クロロ−6−N
−メチル−N−フリルメチルアミノフルオラン、2−(
P−メチルアニリノ)−3−エチル−6−N−メチル−
N−フリルメチルアミノフルオランなどがあげられる。Examples of xanthene coloring agents include rhodamine-B-anilinolactam, rhodamine (p-nitroanilino)lactam, rhodamine (O-chloroanilino)lactam, and 3-
Diethylamino-7,8-benzofluorane, Rhodamine-B-(P-chloroanilinolactam), 2-anilino-3-methyl-6-dimethylaminofluorane, 2-
Anilino-3-methyl-6-N-ethylaminofluorane, 2-anilino-3-methyl-6-N-methyl-N-
(isopropyl)aminofluorane, 2-anilino-3
-Methyl-6-N-methyl-N-cyclohexylaminofluorane, 2-anilino-3-methyl-6-diethylaminofluorane, 2-anilino-3-methyl-6-dibutylaminofluorane, 2-anilino-3 -chloro-
6-dimethylaminofluorane, 2-anilino-3-methyl-6-N-ethyl-N-isoamylaminofluorane, 2-anilino-3-chloro-6-diethylaminofluorane, 2-anilino-3-chloro- 6-N-methyl-N-ethylaminofluorane, 2-anilino-3-chloro-6-N-methyl-N-(isopropyl)aminofluorane, 2-anilino-3-chloro-6-N-methyl- N-cyclohexylaminofluorane, 2-anilino-3-chloro-6-N-methyl-N-pentylaminofluorane, 2-(P-methylanilino)-3-methyl-
6-dimethylaminofluorane, 2-(P-methylanilino)-3-methyl-6-N-methyl-N-ethylaminofluorane, 2-(P-methylanilino)-3-methyl-6-N-methyl- N-(isopropyl)aminofluorane, 2-(P-methylanilino)-3-methyl-6
-N-methyl-N-pentylaminofluorane, 2-(
P-methylanilino)-3-methyl-6-N-methyl-
N-cyclohexylaminofluorane, 2-(P-methylanilino)-3-methyl-6-N-ethyl-N-pentylaminofluorane, 2-(P-methylanilino)-
3-chloro-6-dimethylaminofluorane, 2-(P
-Methyanilino)-3-chloro-6-diethylaminofluorane, 2-(P-methylanilino)-3-chloro-6-N-methyl-N-ethylaminofluorane, 2-
(P-methylanilino)-3-chloro-6-N-methyl-N-(isopropyl)aminofluorane, 2-(P-
methylanilino)-3-chloro-6-N-methyl-N-
Cyclohexylaminofluorane, 2-(P-methylanilino)-3-chloro-6-N-methyl-N-pentylaminofluorane, 2-(P-methylanilino)-3-
Chloro-6-N-ethyl-N-pentylaminofluorane, 2-(P-methylanilino)-3-chloro-6-N
-Methyl-N-furylmethylaminofluorane, 2-(
P-methylanilino)-3-ethyl-6-N-methyl-
Examples include N-furylmethylaminofluorane.
フェノチアジン系発色剤としては、ベンゾイルロイコメ
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 color former include benzoyl leucomethylene blue and p-nitrobenzoyl leucomethylene blue.
スピロピラン系発色剤としては、3−メチル−スピロ−
ジナフトピラン、3−エチル−スピロ−ジナフトピラン
、3.3’−ジクロロ−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−メチル−ナフ
ト−(3−メトキシ−ベンゾ)−スピロピラン、3−プ
ロピル−スピロ−ジベンゾジピランなどがあげられる。As a spiropyran coloring agent, 3-methyl-spiro-
dinaphthopyran, 3-ethyl-spiro-dinaphthopyran, 3,3'-dichloro-spiro-dinaphthopyran, 3-
Examples include benzyl-spiro-dinaphthopyran, 3-methyl-naphtho-(3-methoxy-benzo)-spiropyran, and 3-propyl-spiro-dibenzodipyran.
インドリルフタリド系発色剤としては、3,3−ビス(
1−エチル−2−メチルインドール−3−イル)フタリ
ド、3,3−ビス(1−オクチル−2−メチルインドー
ル−3−イル)フタリド、3−(2−エトキシ−4−ジ
エチルアミノフェニル)−3−(1−エチル−2−メチ
ルインドール−3−イル)フタリド、3−(2−エトキ
シ−4−ジブチルアミノフェニル)−3−(1−エチル
−2−メチルインドール−3−イル)フタリド、3−(
2−アミルオキシ−4−ジエチルアミノフェニル)−3
−(1−エチル−2−メチルインドール−3−イル)フ
タリド、3−(2−エトキシ−4−ジエチルアミノフェ
ニル)−3−(1−オクチル−2−メチルインドール−
3−イル)フタリドなどがあげられる。As an indolylphthalide coloring agent, 3,3-bis(
1-Ethyl-2-methylindol-3-yl)phthalide, 3,3-bis(1-octyl-2-methylindol-3-yl)phthalide, 3-(2-ethoxy-4-diethylaminophenyl)-3 -(1-ethyl-2-methylindol-3-yl)phthalide, 3-(2-ethoxy-4-dibutylaminophenyl)-3-(1-ethyl-2-methylindol-3-yl)phthalide, 3 −(
2-amyloxy-4-diethylaminophenyl)-3
-(1-ethyl-2-methylindol-3-yl)phthalide, 3-(2-ethoxy-4-diethylaminophenyl)-3-(1-octyl-2-methylindole-
Examples include 3-yl) phthalide.
ピリジン系発色剤としては3−(2−エトキシ−4−ジ
エチルアミノフェニル)−3−(1−オクチル−2−メ
チルインドール−3−イル)−7−アザフタリド、3−
(2−エトキシ−4−ジエチルアミノフェニル)−3−
(1−エチル−2−メチルインドール−3−イル)−4
−アザフタリド、3−(2−ヘキシルオキシ−4−ジエ
チルアミノフェニル)−3−(1−エチル−2−メチル
インドール−3−イル)−4−アザフタリドなどがあげ
られる。Examples of pyridine-based coloring agents include 3-(2-ethoxy-4-diethylaminophenyl)-3-(1-octyl-2-methylindol-3-yl)-7-azaphthalide, 3-
(2-ethoxy-4-diethylaminophenyl)-3-
(1-ethyl-2-methylindol-3-yl)-4
-azaphthalide, 3-(2-hexyloxy-4-diethylaminophenyl)-3-(1-ethyl-2-methylindol-3-yl)-4-azaphthalide, and the like.
フルオレン系発色剤としては3’,6’−ビスジエチル
アミノ−5−ジエチルアミノスピロ(インベンゾフラン
−1,9’−フルオレン)−3’−オン、3’,6’−
ビスジエチルアミノ−7−ジエチルアミノ−2−メチル
スピロ(1,3−ベンゾオキサジン−4,9’−フルオ
レン)−3’−オン、3’,6’−ビスジエチルアミノ
−7−ジエチルアミノスピロ(2−ヒドロ−1,3−ベ
ンゾオキサジン−4,9’−フルオレン)−2−オンな
どがあげられる。Examples of fluorene color formers include 3',6'-bisdiethylamino-5-diethylaminospiro(inbenzofuran-1,9'-fluorene)-3'-one, 3',6'-
Bisdiethylamino-7-diethylamino-2-methylspiro(1,3-benzoxazine-4,9'-fluorene)-3'-one, 3',6'-bisdiethylamino-7-diethylaminospiro(2-hydro-1 , 3-benzoxazin-4,9'-fluoren)-2-one, and the like.
これらの発色剤は、単独でまたは二種以上混合して用い
てもよい。These color formers may be used alone or in combination of two or more.
一方、該電子受容性顕色性物質(以下顕色剤と略記)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顕色剤物質が適用される。このよ
うな顕色剤としてはたとえばフェノール性物質、有機ま
たは無機の酸性物質あるいはその塩などがあげられる。On the other hand, as the electron-accepting color-developing substance (hereinafter abbreviated as color-developing agent), various electron-accepting color-developing substances can be used that react with the color former when heated to develop color. Examples of such color developers include phenolic substances, organic or inorganic acidic substances, and salts thereof.
またその具体例としては、たとえば「紙パルプ技術タイ
ムス、(株)テックタイム、30巻6号〜31巻3号」
にて連載されている「感熱記録紙用顕色剤(1)〜(完
)、志賀喬著」および「同誌32巻4号〜32巻10号
」の「感熱記録紙用顕色剤(1)〜(完)、志賀喬著」
に記載されているものがあげられる。具体的には下記の
ものがあげられる。Specific examples include "Paper and Pulp Technology Times, Tech Time Co., Ltd., Vol. 30, No. 6 to Vol. 31, No. 3"
``Color developer for thermal recording paper (1) - (complete), written by Takashi Shiga'' serialized in ``Color developer for thermal recording paper (1) - (complete),'' written by Takashi Shiga, and ``Color developer for thermal recording paper (1)'' published in ``Volume 32, No. 4 to Vol. 32, No. ) ~ (complete), written by Takashi Shiga”
These include those listed in . Specifically, the following can be mentioned.
(1)ビスフェノール系顕色剤
(1−1)非含硫ビスフェノール系顕色剤2−(4−ヒ
ドロキシフェニル)プロパン、2−(3’−ヒドロキシ
フェニル)プロパン、テトラブロムビスフェノールA、
4,4’−イソプロピリデンジフェノール、4,4’−
ブチリデンビス(2−t−ブチル−5−メチルフェノー
ル)などのビスフェノールA誘導体化合物、4,4’−
メチレンビス(2−シクロヘキシル−5−メチルフェノ
ール)、4,4’−イソプロピリデンビス(2−シクロ
ヘキシル−5−メチルフェノール)、 4,4’−ブチ
リデンビス(2−シクロヘキシル−5−メチルフェノー
ル)、4,4’−シクロヘキシリデンビス(2−シクロ
ヘキシル−5−メチルフェノール)、3,3−ビス(3
−シクロヘキシル−4−ヒドロキシ−5−メチルフェノ
ール)ブタン酸エチル、4−[1,1−ビス(4−ヒド
ロキシフェニル)エチル]ビフェニル、2−[1,1−
ビス(4−ヒドロキシフェニル)エチル]ナフタレン、
1−フェニル−1,1−ビス(4−ヒドロキシフェニル
)ブタン、1,1−ビス p−ヒドロキシフェニル)シ
クロヘキサン、4,4’−ブチリデンビス(2−シクロ
ヘキシル−5−メチルフェノール)、メチル−フェニル
−メチリデンビスフェノールなどのビスフェノールA系
関連化合物、1,1−ビス(4−ヒドロキシフェニル)
酢酸、2,2−ビス(4−ヒドロキシフェニル)プロピ
オン酸、ビス(4−ヒドロキシフェニル)酢酸メチルエ
ステル、ビス(4−ヒドロキシフェニル)酢酸−n−ブ
チル、ビス(4−ヒドロキシフェニル)酢酸プロパギル
、ビス(4−ヒドロキシフェニル)酢酸シンナミル、ビ
ス(4−ヒドロキシフエニル)酢酸ベンジル、ビス(4
−ヒドロキシフェニル)酢酸フェニル、ビス(4−ヒド
ロキシフェニル)酢酸フェネチル、ビス(4−ヒドロキ
シフェニル)酢酸−β−(4’−エトキシフェノキシ)
エチル、2,2−ビス(4−ヒドロキシフェニル)酢酸
−3−フェノキシプロピル、2,2−ビス(4−ヒドロ
キシフェニル)吉草酸−β−(4’−メチルフェノキシ
)エチル、ビス(4−ヒドロキシフェニル)ステアリン
酸アミド、1,3−ビス(4−ヒドロキシフェニル)プ
ロパン、2,4−ビス(4−ヒドロキシフェニル)−4
−メチルペンタン、1,3−ジ[2−(4−ヒドロキシ
フェニル)−2−プロピル]ベンゼン、1,3−ジ[2
−(3,5−ジメチル−4−ヒドロキシフェニル)−2
−プロピル]−ベンゼン、ビスフェノール1,1−ビス
(ヒドロキシフェニル)−1−フェニルエタンなどのビ
ス(ヒドロキシフェニル)酸系化合物(1−2)含硫ビ
スフェノール系顕色剤4,4’ジヒドロキシフェニルジ
フェニルスルホン、2,4’ジヒドロキシフェニルジフ
ェニルスルホン、ビス−(3−アリル−4−ヒドロキシ
フェニル)スルホン、ビス−(3−アリル−4−ヒドロ
キシフェニル)スルホン、3−3’−スルホニルビス(
4−ヒドロキシ安息香酸メチルエステル)、1,3−ビ
ス(p−ヒドロキシアニリノスルホニル)ベンゼンなど
のビスフェノールスルホン誘導体;4−ヒドロキシ−4
’−ベンジロキシジフェニルスルホン、4−ヒドロキシ
−4’−イソプロポキシジフエニルスルホンなどのビス
フェノールスルホンのモノエーテル;ビス(3,5−ジ
メチル−4−ヒドロキシフェニル)スルフィド、ビス(
2−メチル−5−イソプロピル−4−ヒドロキシフェニ
ル)スルフィド,4,4’−チオビス(6−ter−ブ
チル−3−メチルフェノール)、1,5−ジ(4−ヒド
ロキシフェニルチオ)−3−オキシペンタン、1,8−
ジ(4−ヒドロキシチオ)−3,6−ジオキサオクタン
、1,3−ジ(4−ヒドロキシフェニルチオ)アセトン
、1,7−ジ(4−ヒドロキシフェニルチオ)−3,5
−ジオン、1,2−ジ(4−ヒドロキシフェニルチオ)
フェニルエタン、1,2−ジ(4−ヒドロキシフェニル
チオ)−1−(4−クロロフェニル)エタン、4−ヒド
ロキシフェニルチオ−4−ヒドロキシフェニル)酢酸メ
チル、ビス(4−ヒドロキシフェニルチオ)酢酸メチル
、4−ベンジルオキシフェニル−4−ヒドロキシフェニ
ルスルフィドなどのビスフェノールスルフィド
(2)ヒドロキシアリールカルボン酸系顕色剤(2−1
)ヒドロキシ安息香酸系顕色剤p−ヒドロキシ安息香酸
、m−ヒドロキシ安息香酸、サルチル酸、p−ヒドロキ
シ安息香酸メチル、p−ヒドロキシ安息香酸ベンジル、
p−ヒドロキシ安息香酸−β−p−メトキシフェノキシ
エチル、p−ヒドロキシ安息香酸−β−フェノキシエチ
ル、p−ヒドロキシ安息香酸−β−p−メトキシフェノ
キシエチル、p−ヒドロキシ安息香酸−2−(o−ヒド
ロキシフェニルチオ)エチルなどのヒドロキシ安息香酸
およびp−ヒドロキシ安息香酸エステル;2,4−ジヒ
ドロキシ安息香酸オクタデシル、2,4−ジヒドロキシ
安息香酸−β−p−エトキシフェノキシエチル、2,4
−ジヒドロキシ安息香酸−β−メタアリロキシエチル、
2,4−ジヒドロキシ安息香酸−β−エチルオキシエチ
ル、2,4−ジヒドロキシ−β−フェニルチオエチル、
1,4−シクロヘキサンジメタノール−ビス−(p−ヒ
ドロキシ安息香酸)エステル、1,4−エチレングリコ
ール−ビス−(p−ヒドロキシ安息香酸)エステルなど
のヒドロキシ安息香酸誘導体
(2−2)サリチル酸系顕色剤
サリチル酸金属塩(Zn、Mg、Ca、Al)、4−テ
トラデシルオキシサリチル酸、4−β−p−トリオキシ
エトキシサリチル酸、3,5−ジ−(α−メチルベンジ
ル)サリチル酸、3,5−ジ−(α,α−ジメチルベン
ジル)サリチル酸、3,5−ジ−ter−ブチルサリチ
ル酸、3−イソプロペニル−5−ter−ブチルサリチ
ル酸、3−ビニル−5−シクロヘキサン酸、3ビニル−
5−ベンジルサリチル酸、5−ミリストイルサリチル酸
、5−フェニルアセチルサリチル酸、メチルフェノキシ
アセチルサリチル酸、4−ミリストイルアミノサリチル
酸、4−フェニルアセチルアミノサリチル酸、2,2−
ビス(3−カルボキシ−4−ヒドロキシフェニル)プロ
パン、1,4−ビス(3−カルボキシ−4−ヒドロキシ
クミル)ベンゼン、ビス(2−ヒドロキシ−3−カルボ
キシ−5−α−フェネチルフェニル)メタンなどのサリ
チル酸誘導体
(2−3)その他のヒドロキシアリールカルボン酸系顕
色剤
4−ヒドロキシフタル酸ジメチル、3,4,5,6−テ
トラクロロフタル酸−モノ−2−ヒドロキシエチルの亜
鉛塩、3,4,5,6−テトラクロロフタル酸−モノ−
3−ヒドロキシ−2,2−ジメチルプロピルの亜鉛塩な
どのフタル酸誘導体、没食子酸−P−クロロベンジル、
没食子酸ベンジル、没食子酸−p−ビニルベンジルなど
の没食子酸誘導体;1−ヒドロキシ−4−ベンジルオキ
シ−2−ナフトエ酸、1−アシルオキシ−4−ベンジル
オキシ−2−ナフトエ酸、2−アシルオキシ−4−ベン
ジルオキシ−1−ナフトエ酸、これらの酸のZn、Mg
などの多価金属塩等のナフトエ酸誘導体
(2−4)その他のカルボン酸系顕色剤o−クマル酸メ
チル、p−クマル酸メチル、o−クマル酸エチル、p−
クマル酸ベンジル、o−クマル酸ナフチルメチル、イン
ドール−2−カルボン酸亜鉛、インドール−2−カルボ
ン酸カルシウム、1−メチルインドール−2−カルボン
酸亜鉛、p−ニトロ安息香酸亜鉛、p−ニトロ安息香酸
錫、L−アスコルビン酸など(3)スルホン系顕色剤
4−ヒドロキシベンゼンスルホン酸メチル、4−ヒドロ
キシ−3−メチル−5−ブロモベンゼンスルホン酸エチ
ル、4−ヒドロキシ−3,5−ジブロモベンゼンスルホ
ン酸エチル、4−ヒドロキシ−4’−メチルジフェニル
スルホン、3’,4’トリメチレン−4−ヒドロキシジ
フェニルスルホン、2−(4−ヒドロキシベンゼンスル
ホニル)ナフタレン、1−(4−ヒドロキシベンゼンス
ルホニル)ナフタレン、3−アリル−4−ヒドロキシ−
4’−メチルジフェニルスルホン、3−アリル−4−ヒ
ドロキシ−4’−メトキシジフェニルスルホン、3−ア
リル−4−ヒドロキシ−4’−(2−フェノキシエトキ
シ)ジフェニルスルホン、3,4−ジヒドロキシフェニ
ル−p−トリルスルホン、2,2’−ビス(4−ヒドロ
キシベンゼンスルホニル)エチルエーテル、4−ヒドロ
キシ−4’−イソプロポキシジフェニルスルホン、4−
ヒドロキシ−4’−クロロジフェニルスルホン、3,5
−ジ−β−フエノキシエトキシカルボニルベンゼンスル
ホン酸、2−β−ナフトキシエトキシナフタレン−6−
スルホン酸などのスルホン系顕色剤;N−ベンゼンスル
ホニル−m−アミノフェノール、N−(α−ナフタレン
スルホニル)−m−アミノフエノール、1,3−ビス(
ρ−ヒドロキシアニリノスルホニルベンゼン、N−(2
−フェノキシエチル)−4−ヒドロキシベンゼンスルホ
ンアミド、N−(3−フェノキシプロピル)−4−ヒド
ロキシベンゼンスルホンアミド、N−(フェニルスルホ
ニル)−p−トルエンスルホンアミド、n−ブチル−N
−(o−カルボキシフェニルスルホニル)−p−アミノ
ベンゾエート、N−(ジメチルスルファモイル)−p−
トルエンスルホンアミド、N,N’−ジフェニルスルホ
ンアミドなどのスルホンアミド化合物;α−ナフタレン
スルホニルクロリド、p−フェニルベンゼンスルホニル
クロリドなどのスルホニルクロリド化合物
これらの顕色剤は単独または二種以上混合して用いても
よい。(1) Bisphenol color developer (1-1) Non-sulfur containing bisphenol color developer 2-(4-hydroxyphenyl)propane, 2-(3'-hydroxyphenyl)propane, tetrabromobisphenol A,
4,4'-isopropylidenediphenol, 4,4'-
Bisphenol A derivative compounds such as butylidene bis(2-t-butyl-5-methylphenol), 4,4'-
Methylenebis(2-cyclohexyl-5-methylphenol), 4,4'-isopropylidenebis(2-cyclohexyl-5-methylphenol), 4,4'-butylidenebis(2-cyclohexyl-5-methylphenol), 4, 4'-cyclohexylidene bis(2-cyclohexyl-5-methylphenol), 3,3-bis(3
-cyclohexyl-4-hydroxy-5-methylphenol)ethyl butanoate, 4-[1,1-bis(4-hydroxyphenyl)ethyl]biphenyl, 2-[1,1-
bis(4-hydroxyphenyl)ethyl]naphthalene,
1-phenyl-1,1-bis(4-hydroxyphenyl)butane, 1,1-bis p-hydroxyphenyl)cyclohexane, 4,4'-butylidenebis(2-cyclohexyl-5-methylphenol), methyl-phenyl- Bisphenol A related compounds such as methylidene bisphenol, 1,1-bis(4-hydroxyphenyl)
Acetic acid, 2,2-bis(4-hydroxyphenyl)propionic acid, bis(4-hydroxyphenyl)acetic acid methyl ester, bis(4-hydroxyphenyl)acetate-n-butyl, bis(4-hydroxyphenyl)propargyl acetate, Bis(4-hydroxyphenyl)cinnamyl acetate, bis(4-hydroxyphenyl)benzyl acetate, bis(4-hydroxyphenyl)acetate
-Hydroxyphenyl)phenyl acetate, bis(4-hydroxyphenyl)phenethyl acetate, bis(4-hydroxyphenyl)acetic acid -β-(4'-ethoxyphenoxy)
Ethyl, 2,2-bis(4-hydroxyphenyl)acetate-3-phenoxypropyl, 2,2-bis(4-hydroxyphenyl)valerate-β-(4'-methylphenoxy)ethyl, bis(4-hydroxy phenyl) stearamide, 1,3-bis(4-hydroxyphenyl)propane, 2,4-bis(4-hydroxyphenyl)-4
-Methylpentane, 1,3-di[2-(4-hydroxyphenyl)-2-propyl]benzene, 1,3-di[2
-(3,5-dimethyl-4-hydroxyphenyl)-2
-propyl]-benzene, bisphenol Bis(hydroxyphenyl) acid compounds such as 1,1-bis(hydroxyphenyl)-1-phenylethane (1-2) Sulfur-containing bisphenol color developer 4,4' dihydroxyphenyl diphenyl Sulfone, 2,4'-dihydroxyphenyldiphenylsulfone, bis-(3-allyl-4-hydroxyphenyl)sulfone, bis-(3-allyl-4-hydroxyphenyl)sulfone, 3-3'-sulfonylbis(
4-hydroxybenzoic acid methyl ester), bisphenolsulfone derivatives such as 1,3-bis(p-hydroxyanilinosulfonyl)benzene; 4-hydroxy-4
Monoethers of bisphenolsulfones such as '-benzyloxydiphenylsulfone, 4-hydroxy-4'-isopropoxydiphenylsulfone; bis(3,5-dimethyl-4-hydroxyphenyl)sulfide, bis(
2-Methyl-5-isopropyl-4-hydroxyphenyl) sulfide, 4,4'-thiobis(6-ter-butyl-3-methylphenol), 1,5-di(4-hydroxyphenylthio)-3-oxy Pentane, 1,8-
Di(4-hydroxythio)-3,6-dioxaoctane, 1,3-di(4-hydroxyphenylthio)acetone, 1,7-di(4-hydroxyphenylthio)-3,5
-dione, 1,2-di(4-hydroxyphenylthio)
Phenylethane, 1,2-di(4-hydroxyphenylthio)-1-(4-chlorophenyl)ethane, methyl 4-hydroxyphenylthio-4-hydroxyphenyl)acetate, methyl bis(4-hydroxyphenylthio)acetate, Bisphenol sulfide such as 4-benzyloxyphenyl-4-hydroxyphenyl sulfide (2) Hydroxyarylcarboxylic acid color developer (2-1
) Hydroxybenzoic acid color developer p-hydroxybenzoic acid, m-hydroxybenzoic acid, salicylic acid, methyl p-hydroxybenzoate, benzyl p-hydroxybenzoate,
p-hydroxybenzoic acid-β-p-methoxyphenoxyethyl, p-hydroxybenzoic acid-β-phenoxyethyl, p-hydroxybenzoic acid-β-p-methoxyphenoxyethyl, p-hydroxybenzoic acid-2-(o- Hydroxybenzoic acid and p-hydroxybenzoic acid esters such as hydroxyphenylthio)ethyl; octadecyl 2,4-dihydroxybenzoate, β-p-ethoxyphenoxyethyl 2,4-dihydroxybenzoate, 2,4
-β-methallyloxyethyl dihydroxybenzoate,
2,4-dihydroxybenzoic acid-β-ethyloxyethyl, 2,4-dihydroxy-β-phenylthioethyl,
Hydroxybenzoic acid derivatives (2-2) salicylic acid derivatives such as 1,4-cyclohexanedimethanol-bis-(p-hydroxybenzoic acid) ester and 1,4-ethylene glycol-bis-(p-hydroxybenzoic acid) ester Coloring agents Salicylic acid metal salts (Zn, Mg, Ca, Al), 4-tetradecyloxysalicylic acid, 4-β-p-trioxyethoxysalicylic acid, 3,5-di-(α-methylbenzyl)salicylic acid, 3,5 -di-(α,α-dimethylbenzyl)salicylic acid, 3,5-di-ter-butylsalicylic acid, 3-isopropenyl-5-ter-butylsalicylic acid, 3-vinyl-5-cyclohexanoic acid, 3-vinyl-
5-Benzylsalicylic acid, 5-myristoylsalicylic acid, 5-phenylacetylsalicylic acid, methylphenoxyacetylsalicylic acid, 4-myristoylaminosalicylic acid, 4-phenylacetylaminosalicylic acid, 2,2-
Bis(3-carboxy-4-hydroxyphenyl)propane, 1,4-bis(3-carboxy-4-hydroxycumyl)benzene, bis(2-hydroxy-3-carboxy-5-α-phenethylphenyl)methane, etc. salicylic acid derivatives (2-3) Other hydroxyarylcarboxylic acid color developers dimethyl 4-hydroxyphthalate, zinc salt of mono-2-hydroxyethyl 3,4,5,6-tetrachlorophthalate, 3, 4,5,6-tetrachlorophthalic acid mono-
Phthalic acid derivatives such as the zinc salt of 3-hydroxy-2,2-dimethylpropyl, P-chlorobenzyl gallate,
Gallic acid derivatives such as benzyl gallate and p-vinylbenzyl gallate; 1-hydroxy-4-benzyloxy-2-naphthoic acid, 1-acyloxy-4-benzyloxy-2-naphthoic acid, 2-acyloxy-4 -benzyloxy-1-naphthoic acid, Zn, Mg of these acids
Naphthoic acid derivatives (2-4) such as polyvalent metal salts such as and other carboxylic acid color developers o-methyl coumarate, p-methyl coumarate, o-ethyl coumarate, p-
Benzyl coumarate, naphthylmethyl o-coumarate, zinc indole-2-carboxylate, calcium indole-2-carboxylate, zinc 1-methylindole-2-carboxylate, zinc p-nitrobenzoate, p-nitrobenzoic acid Tin, L-ascorbic acid, etc. (3) Sulfonic color developer Methyl 4-hydroxybenzenesulfonate, Ethyl 4-hydroxy-3-methyl-5-bromobenzenesulfonate, 4-hydroxy-3,5-dibromobenzenesulfone Ethyl acid, 4-hydroxy-4'-methyldiphenylsulfone, 3',4'trimethylene-4-hydroxydiphenylsulfone, 2-(4-hydroxybenzenesulfonyl)naphthalene, 1-(4-hydroxybenzenesulfonyl)naphthalene, 3 -Allyl-4-hydroxy-
4'-methyldiphenylsulfone, 3-allyl-4-hydroxy-4'-methoxydiphenylsulfone, 3-allyl-4-hydroxy-4'-(2-phenoxyethoxy)diphenylsulfone, 3,4-dihydroxyphenyl-p -Tolylsulfone, 2,2'-bis(4-hydroxybenzenesulfonyl)ethyl ether, 4-hydroxy-4'-isopropoxydiphenylsulfone, 4-
Hydroxy-4'-chlorodiphenylsulfone, 3,5
-di-β-phenoxyethoxycarbonylbenzenesulfonic acid, 2-β-naphthoxyethoxynaphthalene-6-
Sulfonic color developers such as sulfonic acid; N-benzenesulfonyl-m-aminophenol, N-(α-naphthalenesulfonyl)-m-aminophenol, 1,3-bis(
ρ-hydroxyanilinosulfonylbenzene, N-(2
-phenoxyethyl)-4-hydroxybenzenesulfonamide, N-(3-phenoxypropyl)-4-hydroxybenzenesulfonamide, N-(phenylsulfonyl)-p-toluenesulfonamide, n-butyl-N
-(o-carboxyphenylsulfonyl)-p-aminobenzoate, N-(dimethylsulfamoyl)-p-
Sulfonamide compounds such as toluenesulfonamide and N,N'-diphenylsulfonamide; sulfonyl chloride compounds such as α-naphthalenesulfonyl chloride and p-phenylbenzenesulfonyl chloride These color developers may be used alone or in combination of two or more. It's okay.
本発明の増感剤においてテレフタル酸ジメチルエステル
(A)と一般式(1)で示される化合物(B)との重量
比は通常25:75〜80:20、好ましくは30:2
0〜75:25、特に好ましくは35:65〜70:3
0である。(A)が、25未満の場合は感熱記録紙用と
しての感度および耐可塑剤性が低下する。また、(A)
が80を越えると感度が低下する。本発明の増感剤にお
いて(A)および(B)に一般式(2)で示される化合
物(C)を併用すると、更に感度がシャープになる。(
A)+(B)と(C)との重量比は通常95:0〜50
:50、好ましくは90:10〜55:45である。化
合物(C)が50を越えると逆に(A)、(B)のみの
場合より感度は低下する。In the sensitizer of the present invention, the weight ratio of terephthalic acid dimethyl ester (A) to the compound (B) represented by general formula (1) is usually 25:75 to 80:20, preferably 30:2.
0-75:25, particularly preferably 35:65-70:3
It is 0. If (A) is less than 25, the sensitivity and plasticizer resistance for thermal recording paper will decrease. Also, (A)
When the value exceeds 80, the sensitivity decreases. When the compound (C) represented by the general formula (2) is used in combination with (A) and (B) in the sensitizer of the present invention, the sensitivity becomes even sharper. (
The weight ratio of A) + (B) and (C) is usually 95:0 to 50
:50, preferably 90:10 to 55:45. Conversely, when compound (C) exceeds 50, the sensitivity becomes lower than when only (A) and (B) are used.
本発明の(A)、(B)および必要により(C)からな
る増感剤は通常各成分を微粉にし混合して使用する。The sensitizer consisting of (A), (B) and, if necessary, (C) of the present invention is usually used after each component is ground into fine powder and mixed.
本発明の感熱記録用材料において、本発明の増感剤の使
用量は顕色剤100重量部に対して、通常1〜200重
量部、好ましくは3〜100重量部、特に好ましくは1
0〜70重量部である。該増感剤の使用量が1重量部未
満では感熱記録としての感度向上効果が低下し、200
重量部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。In the heat-sensitive recording material of the present invention, the amount of the sensitizer of the present invention used is usually 1 to 200 parts by weight, preferably 3 to 100 parts by weight, particularly preferably 1 to 100 parts by weight.
It is 0 to 70 parts by weight. If the amount of the sensitizer used is less than 1 part by weight, the effect of improving sensitivity as a thermosensitive recording will decrease, and the
If the amount exceeds parts by weight, the sensitivity improvement effect is already saturated and it is uneconomical.
また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発色濃度
が低下し、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 to 70 parts by weight, particularly preferably 20 to 50 parts by weight per 100 parts by weight of the color former. . If the amount of the color developer used is less than 5 parts by weight, the color density will decrease, and if it exceeds 100 parts by weight, the color density will reach an equilibrium, making it uneconomical to use any more.
本発明において該支持体としては紙、合成紙、合成樹脂
フィルムなど好ましくは、紙があげられる。In the present invention, the support is preferably paper, such as paper, synthetic paper, or synthetic resin film.
次に本発明の感熱記録用材料の製造法を例示する。Next, a method for producing the heat-sensitive recording material of the present invention will be illustrated.
増感剤、発色剤および顕色剤を各々含有する懸濁溶液を
製造する。続いてそれぞれの懸濁溶液単独または各種塗
工方法に応じて決められる組合せからなる懸濁溶液混合
物を塗工液とし支持体に塗工し感熱記録用材料を製造す
る。A suspension solution containing each of a sensitizer, a color former, and a color developer is prepared. Subsequently, each suspension solution alone or a suspension solution mixture consisting of a combination determined according to various coating methods is used as a coating solution and coated on a support to produce a heat-sensitive recording material.
各懸濁溶液の製法を例示すると増感剤と結合剤、発色剤
と結合剤および顕色剤と結合剤をそれぞれ水中で必要に
より界面活性剤(2−エチルヘ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
縮合物など)と共にボールミル、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10μ以下、好
ましくは3μ以下の粒子に粉砕、分散し各懸濁溶液が得
られる。An example of how to prepare each suspension solution is to prepare a sensitizer and a binder, a color former and a binder, a color developer and a binder in water, and optionally a surfactant (2-ethylhexylsulfosuccinate soda salt, naphthalenesulfonic acid). A suspension solution is obtained by pulverizing and dispersing the powder into particles of 10 μm or less, preferably 3 μm or less, using a pulverizer such as a ball mill, atrider, or sand grinder.
上記結合剤としては、たとえば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、ポリビニルピロリド
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、イソブチレン/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, ethylcellulose; sodium polyacrylate, polyvinylpyrrolidone, acrylic amide/acrylic ester copolymer,
Acrylic acid amide/acrylic ester/methacrylic acid terpolymer, styrene/maleic anhydride copolymer alkali salt, isobutylene/maleic anhydride copolymer alkali salt, polyacrylamide, sodium alginate, gelatin, casein, etc. In addition to water-soluble polymers, polyvinyl acetate, polyurethane, styrene/butadiene copolymer, polyacrylic acid, polyacrylic acid ester, vinyl chloride/
Latexes such as vinyl acetate copolymer, polybutyl methacrylate, ethylene/vinyl acetate copolymer, and styrene/butadiene/acrylic copolymer can be used.
塗工液は下記表−1で示すように各種の塗工方法に応じ
、懸濁溶液3液混合、2液混合または1液単独のものと
する。As shown in Table 1 below, the coating solution may be a mixture of 3 suspensions, a mixture of 2 suspensions, or a single suspension depending on the various coating methods.
また各塗工液に必要に応じてこの種の感熱記録材料に通
常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、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、クレー、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、ポリ
スチレン樹脂などの有機系の微粉末があげられる。熱可
融性物質としては、たとえばステアリン酸アミド、ステ
アリン酸メチレンビスアミド、オレイン酸アミド、ヤシ
脂肪酸アミドなどの高級脂肪酸アミド、エチレンビスス
テアリルアミドなどのビスアミド、N−デシル−N’−
ラウリル尿素、N−ステアリル−N’−ドコシル尿素な
どの尿素系化合物、その他公知の熱可融性物質などで5
0〜200℃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, titanium oxide, aluminum hydroxide, zinc hydroxide, barium sulfate, clay, kaolin, talc, and surface-treated inorganic fine powders such as calcium carbonate and silica. Examples include organic fine powders such as urea/formalin resin, styrene/methacrylic acid copolymer, and polystyrene resin. Examples of thermofusible substances include stearic acid amide, stearic acid methylene bisamide, oleic acid amide, higher fatty acid amide such as coconut fatty acid amide, bisamide such as ethylene bis stearyl amide, N-decyl-N'-
5 with urea-based compounds such as lauryl urea, N-stearyl-N'-docosyl urea, and other known thermofusible substances.
Examples include those having a melting point of 0 to 200°C.
滑剤としてはステアリン酸亜鉛、ステアリン酸カルシウ
ム塩、ステアリン酸マグネシウム塩、ステアリン酸鉛、
ステアリン酸カドミニウム塩、ステアリン酸バリウム塩
、ステアリン酸アルミニウムなどの高級脂肪酸金属塩の
他に、ステアリン酸、ポリエチレン、カルナバロウ、密
ロウ、パラフィンワックスなどのワックス類があげられ
る。As lubricants, zinc stearate, calcium stearate, magnesium stearate, lead stearate,
Examples include higher fatty acid metal salts such as cadmium stearate, barium stearate, and aluminum stearate, as well as waxes such as stearic acid, polyethylene, carnauba wax, beeswax, and paraffin wax.
塗工液を支持体に塗工する方法としては、たとえば支持
体に塗工液をエアナイフコーター、ブレンドコーター、
ロールコーター、ワイブプレスなどの方法により塗工し
する。また、感熱記録層の形成方法としては、たとえば
表−1に示す塗工液a〜gから選ばれる組合せを各々変
えた下記(I)〜(VII)の方法で感熱記録層を形成
することができる。Examples of methods for applying the coating liquid to the support include applying the coating liquid to the support using an air knife coater, a blend coater,
Coating is done using methods such as roll coater or wipe press. Further, as a method for forming the heat-sensitive recording layer, for example, the heat-sensitive recording layer may be formed by the following methods (I) to (VII) in which the combinations selected from coating liquids a to g shown in Table 1 are changed. can.
(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は増感剤と発色剤と顕色剤の混合した層である
。(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 containing a mixture of a sensitizer, 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)を塗工する。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は増感剤の層である。(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 forming agent and a color developer, and 6 is a layer containing a sensitizer.
(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は増感剤の層
、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 FIG. 3, 6 is a layer of a sensitizer, and 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(f)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は増感剤の層、7は発色剤の層である。(IV) Coating solution (g), coating solution (e), and coating solution (f) are coated on the support in a layered manner. FIG. 4 shows the heat-sensitive recording material obtained. In FIG. 4, 8 is a color developer layer, 6 is a sensitizer layer, 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は増感剤
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 sensitizer layer, 7 is a color former layer, and 8 is a color developer layer.
(VI)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。得られた感熱記録用材
料を第6図に示す。第6図において、3は増感剤と発色
剤の混合した層、4は増感剤と顕色剤の混合した層であ
る。(VI) Coating liquid (b) is coated on the support, and coating liquid (c) is further coated on top of the coating liquid (b). The obtained thermosensitive recording material is shown in FIG. In FIG. 6, 3 is a layer containing a mixture of a sensitizer and a color former, and 4 is a layer containing a mixture of a sensitizer and a color developer.
(VII)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図において、4は増感剤と顕
色剤の混合した層、3は増感剤と発色剤の混合した層で
ある。(VII) 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 in which a sensitizer and a color developer are mixed, and 3 is a layer in which a sensitizer and a color former are mixed.
これらのうち、好ましい感熱記録層の形成方法(II)
(VI)および(VII)である。Among these, preferred method for forming a thermosensitive recording layer (II)
(VI) and (VII).
各層の塗工厚は、感熱記録用材料の形態おょびその他の
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/m2、好ま
しくは1〜15g/m2、特に好ましくは3〜10g/
m2である。The coating thickness of each layer is determined depending on the form of the heat-sensitive recording material and other conditions. The coating amount is not particularly limited, but is usually 0.5 to 20 g/m2, preferably 1 to 15 g/m2, particularly preferably 3 to 10 g/m2 in terms of dry weight.
It is m2.
[実施例]
以下、実施例により本発明をさらに説明するが、不発明
はこれに限定されるものではない。実施例中の部および
%は重量基準である。また実施例中の試験法を下記に示
す。[Examples] Hereinafter, the present invention will be further explained with reference to Examples, but the invention is not limited thereto. Parts and percentages in the examples are by weight. Further, the test methods in the examples are shown below.
(試験法)
(1)発色性
1)動的発色性試験
作成した感熱記録紙をMSI型サーマルヘッド印字装置
を用い動作時間(パルス幅)と発色濃度の関係を試験し
た。0.1〜1.0msec、電圧22V。発色濃度は
マクベス濃度計(マクベス社製)を用い反射濃度を測定
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 Development 1) Dynamic Color Development Test The prepared thermal recording paper was tested for the relationship between operating time (pulse width) and color density using an MSI type thermal head printing device. 0.1 to 1.0 msec, voltage 22V. The color density was determined by measuring the reflection density using a Macbeth densitometer (manufactured by Macbeth). The larger the value, the higher the color density.
2)静的発色性試験
作成した感熱記録紙を熱傾斜ヒートシーラーを用い温度
幅70℃〜100℃、印圧2kg/cm、圧着時間2秒
の条件で発色させ色濃度を測定した。濃度計は1)に同
じ。2) Static color development test The prepared thermosensitive recording paper was colored using a thermal gradient heat sealer under conditions of a temperature range of 70° C. to 100° C., a printing pressure of 2 kg/cm, and a pressing time of 2 seconds, and the color density was measured. The concentration meter is the same as 1).
(2)白色度(地肌カブリ)
感熱記録紙の発色させる前のハンター白度、B値を M
ulti Spectro Colour Meter
MSC−2型を用い測定した。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 fog) Hunter whiteness before coloring of thermal recording paper, B value is M
ulti Spectro Color Meter
Measurement was performed using MSC-2 type. The larger the value, the higher the degree of whiteness.
(3)耐光性
発色性試験で発色させた画像部をフェードメーターを用
い80℃、72時間照射し、照射部色濃度を測定した。(3) Light resistance The colored image area was irradiated for 72 hours at 80° C. using a fade meter, and the color density of the irradiated area was measured.
濃度計は1)に同じ。The concentration meter is the same as 1).
(4)耐湿性試験
発色性試験で発色させた面像部を45℃、90%RHの
恒温恒湿槽中に24時間放置後画像部の色濃度を測定し
た。濃度計は1)に同じ。(4) Humidity Resistance Test The surface image area colored in the color development test was left in a constant temperature and humidity bath at 45° C. and 90% RH for 24 hours, and then the color density of the image area was measured. The concentration meter is the same as 1).
(5)耐可塑剤性試験
プラスチック消しゴムを発色性試験で予め発色させた画
像部の上にのせ24時間放置後、面像部の色濃度を測定
した。濃度計は1)に同じ。(5) Plasticizer Resistance Test A plastic eraser was placed on the image area that had been colored in advance in the color development test, and after being left for 24 hours, the color density of the surface image area was measured. The concentration meter is the same as 1).
実施例1〜6、比較例1〜7
製造例1〜6および比較製造例1〜7
表−2に示す各化合物を各々細粉砕し、各々表−2(1
)に示す比率で混合して本発明の増感剤■〜■を得た。Examples 1 to 6, Comparative Examples 1 to 7 Production Examples 1 to 6 and Comparative Production Examples 1 to 7 Each of the compounds shown in Table-2 was finely ground, and
) to obtain sensitizers ① to ② of the present invention.
また比較製造例の増感剤■〜■は各々表−2(2)に示
す各化合物を細粉砕して得た。比較製造例の増感剤■、
■は表−2(2)に示す各化合物を150℃にて混合溶
融し、冷却後細粉砕して得た。Sensitizers (1) to (2) of Comparative Production Examples were each obtained by finely pulverizing each compound shown in Table 2 (2). Comparative production example sensitizer■,
(2) was obtained by mixing and melting the compounds shown in Table 2 (2) at 150°C, cooling and finely pulverizing the mixture.
表−3〜5に各々にA、BBおよびCC液をそれぞれボ
ールミルにて24時間粉砕、分散した後、各液を表−7
に示す組合せで充分混合し実施例1〜6の塗工液を作成
した、この塗工液を上質紙(坪量50g/m2)上に乾
燥固形分量6g/m2となるようにドクターブレードで
塗工し、乾燥後、実施例1〜6の本発明の感熱記録用材
料を作成した。Tables 3 to 5 show that after pulverizing and dispersing liquids A, BB and CC in a ball mill for 24 hours, each liquid was added to Table 7.
The coating liquids of Examples 1 to 6 were prepared by thoroughly mixing the combinations shown in .This coating liquid was coated with a doctor blade on high-quality paper (basis weight 50 g/m2) so that the dry solid content was 6 g/m2. After processing and drying, heat-sensitive recording materials of the present invention of Examples 1 to 6 were prepared.
また、AA液の代わりに表−6に示す従来の増感剤の懸
濁溶液を各々用い、且つ表−7に示す組合せの代わりに
表−8に示す組合せを用いる以外は上記同様に行い、表
−8に示す比較例1〜7の塗工液および感熱記録用材料
を作成した。得られた実施例1〜6および比較例1〜7
の感熱記録用材料の各性能を測定した結果を表−9〜1
1に示す。In addition, the same procedure as above was carried out except that the conventional sensitizer suspension solutions shown in Table 6 were used instead of the AA solution, and the combinations shown in Table 8 were used instead of the combinations shown in Table 7. Coating liquids and heat-sensitive recording materials of Comparative Examples 1 to 7 shown in Table 8 were prepared. Obtained Examples 1 to 6 and Comparative Examples 1 to 7
Tables 9 to 1 show the results of measuring each performance of the heat-sensitive recording material.
Shown in 1.
性はいずれも従来の感熱記録紙に比べすぐれていた。Both properties were superior to conventional thermal recording paper.
とくに比較例1および2では使用した増感剤■はmpが
142℃、増感剤■はmpが192℃(いずれも従来の
増感剤)と高いため感度が著しく悪いものであった。In particular, in Comparative Examples 1 and 2, the sensitizer (2) used had a high mp of 142°C, and the sensitizer (2) had a high mp of 192°C (both conventional sensitizers), resulting in extremely poor sensitivity.
製造例7
製造例1〜6と同様にして表−12に示す化合物を各々
細粉砕し、混合し本発明の増感剤■を得た。Production Example 7 In the same manner as in Production Examples 1 to 6, the compounds shown in Table 12 were each finely ground and mixed to obtain a sensitizer (2) of the present invention.
実施例7〜9、比較例8
下記のDDおよびEE液をボールミルにて24時間粉砕
、分散し懸濁溶液を得た。この溶液を上質紙(坪量60
g/m2)に(I),(VI)および(VII)の方法
、すなわち(I)は紙にDD液とEE液の混合液(1/
1重量比)を乾燥固形分量8g/m2となるようにドク
ターブレードにて塗工し乾燥した。(VI)は紙に塗工
液DD液を乾燥固形分量4g/m2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EE液
を同様に塗工、乾燥した。(VII)は(VI)の逆で
、先にEE液を塗工し、次いでDD液を塗工した。塗工
量は(VI)と同じとした。Examples 7 to 9, Comparative Example 8 The following DD and EE solutions were ground and dispersed in a ball mill for 24 hours to obtain a suspension solution. Spread this solution on high-quality paper (basis weight 60)
g/m2) to methods (I), (VI) and (VII), that is, (I) is a mixture of DD liquid and EE liquid (1/2 g/m2) on paper.
1 weight ratio) with a doctor blade to a dry solid content of 8 g/m 2 and dried. For (VI), the coating liquid DD was applied to paper using a doctor blade so that the dry solid content was 4 g/m 2 , and then the coating liquid EE was similarly applied onto this layer and dried. (VII) is the opposite of (VI), in which the EE liquid was applied first, and then the DD liquid was applied. The coating amount was the same as (VI).
[DD液:増感剤と発色剤の混合懸濁溶液]増感剤■
10部
2−アニリノ−3−メチル−6−ジブチルアミノフルオ
ラン 15部
ステアリン酸亜鉛 5部
炭酸カルシウム 5部
ポリビニルアルコール(10%水溶液) 35部水 3
0部
[EE液:増感剤と顕色剤の混合懸濁液]増感剤■ 1
0部
ビスフェノールA 20部
ステアリン酸亜鉛 5部
1,5−ジ(4−ヒドロキシフェニルチオ)−3−オキ
サペンタン 10部
炭酸カルシウム 5部
ポリビニルアルコール(10%水溶液) 35部水 1
5部
塗工方法(I)、(VI)および(VII)で作成した
感熱記録材料をそれぞれ実施例7、8および9とした。[DD solution: mixed suspension solution of sensitizer and color former] Sensitizer ■
10 parts 2-anilino-3-methyl-6-dibutylaminofluorane 15 parts zinc stearate 5 parts calcium carbonate 5 parts polyvinyl alcohol (10% aqueous solution) 35 parts water 3
0 parts [EE liquid: mixed suspension of sensitizer and developer] Sensitizer ■ 1
0 parts Bisphenol A 20 parts Zinc stearate 5 parts 1,5-di(4-hydroxyphenylthio)-3-oxapentane 10 parts Calcium carbonate 5 parts Polyvinyl alcohol (10% aqueous solution) 35 parts Water 1
Thermal recording materials prepared by the 5-part coating methods (I), (VI) and (VII) were designated as Examples 7, 8 and 9, respectively.
また比較例8として、DDおよびEE液の増感剤■の代
わりに、P−ベンジルビフエニルを用いて(I)の塗工
方法で塗工し感熱記録材料(比較例8)を作成した。次
いで実施例7〜9および比較例8の感熱記録材料の性能
を測定した結果を表−13〜15に示す。Further, as Comparative Example 8, a heat-sensitive recording material (Comparative Example 8) was prepared by using P-benzylbiphenyl instead of the sensitizer (1) in the DD and EE solutions and applying the coating method in (I). Next, the results of measuring the performance of the heat-sensitive recording materials of Examples 7 to 9 and Comparative Example 8 are shown in Tables 13 to 15.
表−8〜10から明らかなように本発明の感熱記録材料
の発色性、耐光性、耐湿性および耐可塑剤性は従来の感
熱記録材料ものに比べすぐれていた。As is clear from Tables 8 to 10, the color development, light resistance, moisture resistance, and plasticizer resistance of the heat-sensitive recording materials of the present invention were superior to those of conventional heat-sensitive recording materials.
また、(VI)の塗工方法による感熱記録用材料(実施
例8)が最もすぐれていた。Furthermore, the heat-sensitive recording material (Example 8) produced by the coating method (VI) was the most excellent.
[発明の効果]
本発明の増感剤を含有する本発明の感熱記録用材料は、
従来のものに比べて高級脂肪酸金属塩などの滑剤を添加
した場合でも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。[Effect of the invention] The thermal recording material of the invention containing the sensitizer of the invention has the following properties:
Compared to conventional products, even when a lubricant such as a higher fatty acid metal salt is added, the color development sensitivity is significantly better and the whiteness (background fog) is excellent.
また、画像部は耐光性、耐湿性および耐可塑剤性など高
品位の性能を提供する。Additionally, the image area provides high quality performance such as light fastness, moisture resistance and plasticizer resistance.
これらの効果を奏することから、本発明の増感剤および
感熱記録用材料はファクシミリ、POSラベルなどの各
種の記録用材料に有用である。Because of these effects, the sensitizer and heat-sensitive recording material of the present invention are useful for various recording materials such as facsimiles and POS labels.
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…増感剤と発色剤と顕色剤の混合した層
、3…増感剤と発色剤の混合した層、4…増感剤と顕色
剤の混合した層、5…発色剤と顕色剤の混合した層6…
増感剤の層、7…発色剤の層、
8…顕色剤の層FIGS. 1 to 7 are explanatory views (cross-sectional views) of the heat-sensitive recording material of the present invention. 1...Support, 2...A layer containing a mixture of a sensitizer, a color former and a color developer, 3...A layer containing a mixture of a sensitizer and a color former, 4...A layer containing a mixture of a sensitizer and a color developer, 5 ...Layer 6 containing a mixture of color forming agent and color developer...
Sensitizer layer, 7...color former layer, 8...color developer layer
Claims (7)
般式 {式中、R1は置換基を有していてもよい(チオ)フェ
ノール類残基、Xは炭素数1〜4のアルキレン基、Yは
OまたはS原子、R2は脂肪族炭化水素基、脂肪族モノ
カルボン酸残基または式[式中、R3はジカルボン酸残
基または−CH2−、R4は置換基を有していてもよい
(チオ)フェノール類残基、Xは炭素数1〜4のアルキ
レン基、YはOまたはS原子、nは1〜3の整数を表す
。]で示される基、mは1〜3の整数を表す。}で示さ
れる化合物(B)、 および必要により一般式 [式中、R5およびR6は、置換基を有していてもよい
(チオ)フェノール類残基、YはOまたはS原子を表す
。]で示される化合物(C)からなることを特徴とする
感熱記録用増感剤。Claim 1: Terephthalic acid dimethyl ester (A), general formula {wherein R1 is a (thio)phenol residue which may have a substituent, X is an alkylene group having 1 to 4 carbon atoms, Y is an O or S atom, R2 is an aliphatic hydrocarbon group, an aliphatic monocarboxylic acid residue or a formula [wherein R3 is a dicarboxylic acid residue or -CH2-, R4 may have a substituent] thio)phenol residue, X represents an alkylene group having 1 to 4 carbon atoms, Y represents an O or S atom, and n represents an integer of 1 to 3. ], m represents an integer of 1 to 3. }, and optionally a compound represented by the general formula [wherein R5 and R6 are (thio)phenol residues which may have a substituent, and Y represents an O or S atom. ] A sensitizer for thermal recording characterized by comprising a compound (C) represented by the following.
求項1記載の増感剤。2. The sensitizer according to claim 1, wherein the content of (A) is 25% by weight or more.
ウ酸残 基またはフマル酸残基である請求項1または2記載の増
感剤。3. The sensitizer according to claim 1 or 2, wherein R1 is a phenol residue and R2 is an oxalic acid residue or a fumaric acid residue.
供与 性無色発色剤と電子受容性顕色性物質を含有し、且つ熱
により発色する感熱記録用材料において、請求項1〜3
のいずれか記載の増感剤を支持体上に形成される層に含
有することを特徴とする感熱記録用材料。4. A heat-sensitive recording material which contains at least an electron-donating colorless coloring agent and an electron-accepting color developer in a layer formed on a support, and which develops color when heated.
A heat-sensitive recording material, characterized in that a layer formed on a support contains the sensitizer according to any one of the above.
色発 色剤および該電子受容性顕色性物が混合した層と該増感
剤の層とを積層 した層である請求項4記載の感熱記録用材料。5. A layer formed on the support is a laminated layer of a layer containing a mixture of the electron-donating colorless color former and the electron-accepting color developer, and a layer of the sensitizer. 4. The heat-sensitive recording material described in 4.
該電子供与性無色発色剤が混合した層と、該増感 剤および該電子受容性顕色性物質が混合した層とを積層
した層である請求項4記載の感熱記録用材料。6. The layer formed on the support is a layer in which the sensitizer and the electron-donating colorless coloring agent are mixed, and a layer in which the sensitizer and the electron-accepting color developer are mixed. 5. The heat-sensitive recording material according to claim 4, which is a laminated layer of.
該電子受容性顕色性物質が混合した層と該増感剤 および電子供与性無色発色剤が混合した層とを積層した
層である請求項4記載の感熱記録用材料。7. The layer formed on the support is a laminate of a layer containing a mixture of the sensitizer and the electron-accepting color developer and a layer containing a mixture of the sensitizer and the electron-donating colorless color former. 5. The heat-sensitive recording material according to claim 4, which is a layer comprising:
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2226360A JPH04219280A (en) | 1990-08-27 | 1990-08-27 | Sensitizer for thermal recording and thermal recording material |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2226360A JPH04219280A (en) | 1990-08-27 | 1990-08-27 | Sensitizer for thermal recording and thermal recording material |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH04219280A true JPH04219280A (en) | 1992-08-10 |
Family
ID=16843930
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2226360A Pending JPH04219280A (en) | 1990-08-27 | 1990-08-27 | Sensitizer for thermal recording and thermal recording material |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH04219280A (en) |
-
1990
- 1990-08-27 JP JP2226360A patent/JPH04219280A/en active Pending
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