JPWO2013154006A1 - Thermal recording material - Google Patents
Thermal recording material Download PDFInfo
- Publication number
- JPWO2013154006A1 JPWO2013154006A1 JP2014510126A JP2014510126A JPWO2013154006A1 JP WO2013154006 A1 JPWO2013154006 A1 JP WO2013154006A1 JP 2014510126 A JP2014510126 A JP 2014510126A JP 2014510126 A JP2014510126 A JP 2014510126A JP WO2013154006 A1 JPWO2013154006 A1 JP WO2013154006A1
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- JP
- Japan
- Prior art keywords
- compound
- acid
- recording material
- bis
- heat
- 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
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- 239000000463 material Substances 0.000 title claims abstract description 32
- -1 phenol compound Chemical class 0.000 claims abstract description 81
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 44
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 30
- 229920003986 novolac Polymers 0.000 claims abstract description 14
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000004040 coloring Methods 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 18
- 229920005989 resin Polymers 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000007788 liquid Substances 0.000 description 19
- 239000011248 coating agent Substances 0.000 description 18
- 238000000576 coating method Methods 0.000 description 18
- 239000002245 particle Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000004372 Polyvinyl alcohol Substances 0.000 description 12
- 239000000975 dye Substances 0.000 description 12
- 229920002451 polyvinyl alcohol Polymers 0.000 description 12
- 239000000945 filler Substances 0.000 description 11
- 239000000654 additive Substances 0.000 description 10
- 239000011230 binding agent Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 9
- 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 8
- 238000011161 development Methods 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- 239000001993 wax Substances 0.000 description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical class C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 4
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Chemical class 0.000 description 4
- 239000002184 metal Chemical class 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- RMVRSNDYEFQCLF-UHFFFAOYSA-N phenyl mercaptan Natural products SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 3
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 3
- 239000004816 latex Substances 0.000 description 3
- 229920000126 latex Polymers 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000005011 phenolic resin Substances 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- 229920005992 thermoplastic resin Polymers 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-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
- YFHKLSPMRRWLKI-UHFFFAOYSA-N 2-tert-butyl-4-(3-tert-butyl-4-hydroxy-5-methylphenyl)sulfanyl-6-methylphenol Chemical compound CC(C)(C)C1=C(O)C(C)=CC(SC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 YFHKLSPMRRWLKI-UHFFFAOYSA-N 0.000 description 2
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 2
- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 150000008378 aryl ethers 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 class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 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
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 239000004088 foaming agent Substances 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 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 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003413 spiro compounds Chemical class 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea group Chemical class NC(=S)N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
- BITJPPJAVHCIOK-UHFFFAOYSA-N (2-hydroxy-4-methoxy-5-methylphenyl)-phenylmethanone Chemical compound C1=C(C)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 BITJPPJAVHCIOK-UHFFFAOYSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 1
- FWHYSYZWOFUAAH-UHFFFAOYSA-N (4-methylphenyl) 2,4,6-trimethylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1OS(=O)(=O)C1=C(C)C=C(C)C=C1C FWHYSYZWOFUAAH-UHFFFAOYSA-N 0.000 description 1
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- DDMUCNBBNKTNCX-UHFFFAOYSA-N 1,3-bis(3-chlorophenyl)thiourea Chemical compound ClC1=CC=CC(NC(=S)NC=2C=C(Cl)C=CC=2)=C1 DDMUCNBBNKTNCX-UHFFFAOYSA-N 0.000 description 1
- QCZZSANNLWPGEA-UHFFFAOYSA-N 1-(4-phenylphenyl)ethanone Chemical group C1=CC(C(=O)C)=CC=C1C1=CC=CC=C1 QCZZSANNLWPGEA-UHFFFAOYSA-N 0.000 description 1
- YBRXHRWLEFCFEG-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-methylbenzene Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C1=CC=CC=C1 YBRXHRWLEFCFEG-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
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- IYQIAVRZWFMVGZ-UHFFFAOYSA-N 1-methoxy-4-(2-phenoxyethoxy)benzene Chemical compound C1=CC(OC)=CC=C1OCCOC1=CC=CC=C1 IYQIAVRZWFMVGZ-UHFFFAOYSA-N 0.000 description 1
- VGMACPCJKUXETI-UHFFFAOYSA-N 1-methoxy-4-[2-(4-methoxyphenoxy)ethoxy]benzene Chemical compound C1=CC(OC)=CC=C1OCCOC1=CC=C(OC)C=C1 VGMACPCJKUXETI-UHFFFAOYSA-N 0.000 description 1
- OAGNKYSIOSDNIG-UHFFFAOYSA-N 1-methyl-3-[2-(3-methylphenoxy)ethoxy]benzene Chemical compound CC1=CC=CC(OCCOC=2C=C(C)C=CC=2)=C1 OAGNKYSIOSDNIG-UHFFFAOYSA-N 0.000 description 1
- JWSWULLEVAMIJK-UHFFFAOYSA-N 1-phenylmethoxynaphthalene Chemical compound C=1C=CC2=CC=CC=C2C=1OCC1=CC=CC=C1 JWSWULLEVAMIJK-UHFFFAOYSA-N 0.000 description 1
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 description 1
- JHJUYGMZIWDHMO-UHFFFAOYSA-N 2,6-dibromo-4-(3,5-dibromo-4-hydroxyphenyl)sulfonylphenol Chemical compound C1=C(Br)C(O)=C(Br)C=C1S(=O)(=O)C1=CC(Br)=C(O)C(Br)=C1 JHJUYGMZIWDHMO-UHFFFAOYSA-N 0.000 description 1
- QFKZBYXKHJHWSO-UHFFFAOYSA-N 2-(4-aminophenyl)-3-[4-(dimethylamino)phenyl]propanenitrile Chemical compound C1=CC(N(C)C)=CC=C1CC(C#N)C1=CC=C(N)C=C1 QFKZBYXKHJHWSO-UHFFFAOYSA-N 0.000 description 1
- LROZSPADHSXFJA-UHFFFAOYSA-N 2-(4-hydroxyphenyl)sulfonylphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=CC=C1O LROZSPADHSXFJA-UHFFFAOYSA-N 0.000 description 1
- ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 description 1
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- ITLDHFORLZTRJI-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-5-octoxyphenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1N1N=C2C=CC=CC2=N1 ITLDHFORLZTRJI-UHFFFAOYSA-N 0.000 description 1
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- WLTCCDHHWYAMCG-UHFFFAOYSA-N 2-phenylmethoxynaphthalene Chemical compound C=1C=C2C=CC=CC2=CC=1OCC1=CC=CC=C1 WLTCCDHHWYAMCG-UHFFFAOYSA-N 0.000 description 1
- NQQDJQMOEYVMCD-UHFFFAOYSA-N 2-tert-butyl-4-[1-(3-tert-butyl-4-hydroxy-5-methylphenyl)butyl]-6-methylphenol Chemical compound C=1C(C)=C(O)C(C(C)(C)C)=CC=1C(CCC)C1=CC(C)=C(O)C(C(C)(C)C)=C1 NQQDJQMOEYVMCD-UHFFFAOYSA-N 0.000 description 1
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- GPNYZBKIGXGYNU-UHFFFAOYSA-N 2-tert-butyl-6-[(3-tert-butyl-5-ethyl-2-hydroxyphenyl)methyl]-4-ethylphenol Chemical compound CC(C)(C)C1=CC(CC)=CC(CC=2C(=C(C=C(CC)C=2)C(C)(C)C)O)=C1O GPNYZBKIGXGYNU-UHFFFAOYSA-N 0.000 description 1
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- XTUPUYCJWKHGSW-UHFFFAOYSA-L zinc;2-carboxy-4,6-bis(1-phenylethyl)phenolate Chemical compound [Zn+2].C=1C(C(C)C=2C=CC=CC=2)=C(O)C(C([O-])=O)=CC=1C(C)C1=CC=CC=C1.C=1C(C(C)C=2C=CC=CC=2)=C(O)C(C([O-])=O)=CC=1C(C)C1=CC=CC=C1 XTUPUYCJWKHGSW-UHFFFAOYSA-L 0.000 description 1
- NDPSWYMNYJXGGH-UHFFFAOYSA-L zinc;3-acetyloxynaphthalene-2-carboxylate Chemical compound [Zn+2].C1=CC=C2C=C(C([O-])=O)C(OC(=O)C)=CC2=C1.C1=CC=C2C=C(C([O-])=O)C(OC(=O)C)=CC2=C1 NDPSWYMNYJXGGH-UHFFFAOYSA-L 0.000 description 1
- MLVWCBYTEFCFSG-UHFFFAOYSA-L zinc;dithiocyanate Chemical compound [Zn+2].[S-]C#N.[S-]C#N MLVWCBYTEFCFSG-UHFFFAOYSA-L 0.000 description 1
- MTYHLWRUYCUTPA-UHFFFAOYSA-L zinc;naphthalene-1-carboxylate Chemical compound [Zn+2].C1=CC=C2C(C(=O)[O-])=CC=CC2=C1.C1=CC=C2C(C(=O)[O-])=CC=CC2=C1 MTYHLWRUYCUTPA-UHFFFAOYSA-L 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/333—Colour developing components therefor, e.g. acidic compounds
- B41M5/3331—Macromolecular compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/323—Organic colour formers, e.g. leuco dyes
- B41M5/327—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
- B41M5/3275—Fluoran compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/333—Colour developing components therefor, e.g. acidic compounds
- B41M5/3333—Non-macromolecular compounds
- B41M5/3335—Compounds containing phenolic or carboxylic acid groups or metal salts thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/333—Colour developing components therefor, e.g. acidic compounds
- B41M5/3333—Non-macromolecular compounds
- B41M5/3335—Compounds containing phenolic or carboxylic acid groups or metal salts thereof
- B41M5/3336—Sulfur compounds, e.g. sulfones, sulfides, sulfonamides
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Abstract
ロイコ染料、顕色剤、及び、4−t−ブチルフェノールを含むフェノール化合物とホルムアルデヒドとから形成されるフェノールノボラック樹脂を含有する感熱発色層を備える、感熱記録材料が開示される。Disclosed is a heat-sensitive recording material comprising a heat-sensitive color developing layer containing a leuco dye, a developer, and a phenol novolac resin formed from a phenol compound containing 4-t-butylphenol and formaldehyde.
Description
本発明は、感熱記録材料に関する。 The present invention relates to a heat-sensitive recording material.
感熱記録材料は、一般に、無色又は淡色の染料と、顕色剤とを主成分として含有する感熱発色層を紙、フィルム、合成紙等の支持体上に形成した構造を有する。加熱により染料と顕色剤が溶融及び接触して起こる化学反応により感熱発色層が発色して、発色記録を得る。 The heat-sensitive recording material generally has a structure in which a heat-sensitive coloring layer containing a colorless or light-colored dye and a developer as main components is formed on a support such as paper, film or synthetic paper. The heat-sensitive color forming layer develops color by a chemical reaction that occurs when the dye and the developer are melted and brought into contact with heating to obtain a color record.
近年、小売店、コンビニエンスストア、ス−パーマーケット等におけるPOSシステムへの移行、交通機関における自動化システムに伴って、ラベル類、乗車券及び回数券等への感熱記録材料の使用が普及している。これらの用途においては、感熱記録材料の高い保存安定性が望まれている。 In recent years, with the shift to POS systems in retail stores, convenience stores, supermarkets, etc., and the use of automation systems in transportation, the use of heat-sensitive recording materials for labels, tickets, coupon tickets, etc. has become widespread. . In these applications, high storage stability of the thermosensitive recording material is desired.
これまでにも、感熱記録材料の顕色剤等についての検討がなされている(例えば、特許文献1、2)。 So far, studies have been made on the color developer of the heat-sensitive recording material (for example, Patent Documents 1 and 2).
しかし、従来の感熱記録材料は、光によって画像部(発色部分)が退色したり、地肌部(発色部分以外の部分)での発色が進行したりし易い傾向があり、特に耐光性の点で更なる改善が求められている。 However, conventional heat-sensitive recording materials tend to cause fading of the image area (colored portion) due to light, or color development on the background portion (portion other than the colored portion), particularly in terms of light resistance. Further improvement is required.
そこで、本発明は、感熱記録材料の耐光性の更なる向上を主な目的とする。 Therefore, the main object of the present invention is to further improve the light resistance of the thermosensitive recording material.
本発明は、ロイコ染料、顕色剤、及び、4−t−ブチルフェノールを含むフェノール化合物とホルムアルデヒドとから形成されるフェノールノボラック樹脂を含有する感熱発色層を備える感熱記録材料に関する。 The present invention relates to a thermosensitive recording material comprising a thermosensitive coloring layer containing a phenol novolac resin formed from a leuco dye, a developer, and a phenol compound containing 4-t-butylphenol and formaldehyde.
本発明者らの知見によれば、顕色剤に加えて、顕色助剤として上記特定のフェノールノボラック樹脂を用いることにより、感熱記録材料の耐光性を改善することが可能である。 According to the knowledge of the present inventors, it is possible to improve the light resistance of the heat-sensitive recording material by using the specific phenol novolac resin as a color developing aid in addition to the color developer.
顕色剤は、フェノール性水酸基を有し上記フェノールノボラック樹脂とは異なるフェノール化合物、及びウレア基を有する尿素化合物から選ばれる少なくとも1種の化合物を含んでもよい。これら化合物を含む顕色剤と、上記顕色助剤との組み合わせにより、従来と比較して特に顕著な耐光性向上の効果を得ることができる。 The developer may contain at least one compound selected from a phenol compound having a phenolic hydroxyl group and different from the phenol novolac resin and a urea compound having a urea group. The combination of the color developer containing these compounds and the color development aid can provide a particularly remarkable effect of improving light resistance as compared with the conventional color developer.
本発明によれば、感熱記録材料の耐光性の更なる向上を図ることができる。また、本発明に係る感熱記録材料は、良好な耐熱性及び耐水性も有する。 According to the present invention, the light resistance of the thermosensitive recording material can be further improved. The heat-sensitive recording material according to the present invention also has good heat resistance and water resistance.
以下、本発明の好適な実施形態について詳細に説明する。ただし、本発明は以下の実施形態に限定されるものではない。 Hereinafter, preferred embodiments of the present invention will be described in detail. However, the present invention is not limited to the following embodiments.
図1は、感熱記録材料の一実施形態を示す断面図である。図1に示す感熱記録材料10は、主として、シート状の支持体1と、支持体1の一方の面側に設けられた感熱発色層3とから構成される。感熱発色層3と支持体1との間に中間層5が更に設けられていてもよい。
FIG. 1 is a cross-sectional view showing an embodiment of a heat-sensitive recording material. A heat-
支持体1としては、紙、プラスチックシート、合成紙等が用いられる。 As the support 1, paper, plastic sheet, synthetic paper, or the like is used.
感熱発色層3は、発色性化合物としてのロイコ染料と、顕色剤と、4−t−ブチルフェノールを含むフェノール化合物とホルムアルデヒドとから形成されるフェノールノボラック樹脂とを含有する。
The
上記フェノールノボラック樹脂は、顕色剤との組み合わせにより発色性能を改良するために用いられる顕色助剤として、感熱発色層に含有される。このフェノールノボラック樹脂は、例えば、4−t−ブチルフェノール及びフェノールとホルムアルデヒドとから、酸触媒の存在下で合成することができる。酸触媒の存在下で合成された上記フェノールノボラック樹脂において、6以上の核(ベンゼン環)を有する縮合物の割合は、20質量%以上、又は50質量%以上であってもよい。これにより、本発明による効果がより顕著に奏される。 The phenol novolac resin is contained in the heat-sensitive color developing layer as a color development aid used for improving the color development performance in combination with a color developer. This phenol novolac resin can be synthesized, for example, from 4-t-butylphenol and phenol and formaldehyde in the presence of an acid catalyst. In the above phenol novolak resin synthesized in the presence of an acid catalyst, the proportion of the condensate having 6 or more nuclei (benzene rings) may be 20% by mass or more, or 50% by mass or more. Thereby, the effect by this invention is show | played more notably.
感熱発色剤に含まれる顕色剤として、電子受容性の種々の化合物、例えば、フェノール性水酸基を有し上記フェノールノボラック樹脂とは異なるフェノール化合物、フェニル基に結合したチオール基を有するチオフェノール化合物、ウレア基を有する尿素化合物、チオウレア基を有するチオ尿素化合物、有機酸及びその金属塩を使用することができる。 As the color developer contained in the heat-sensitive color former, various electron-accepting compounds, for example, a phenol compound having a phenolic hydroxyl group and different from the phenol novolak resin, a thiophenol compound having a thiol group bonded to a phenyl group, Urea compounds having a urea group, thiourea compounds having a thiourea group, organic acids and metal salts thereof can be used.
顕色剤としてのフェノール化合物は、4−t−ブチルフェノールを含まないフェノール化合物とホルムアルデヒドとから形成されるフェノール樹脂(例えば、フェノールとホルムアルデヒドとから形成されるフェノールノボラック樹脂)、ビスフェノールA及びビスフェノールS等のビスフェノール化合物であってもよい。フェノール化合物は、例えば、α−ナフトール、β−ナフトール、p−オクチルフェノール、4−t−オクチルフェノール、p−t−ブチルフェノール、p−フェニルフェノール、1,1−ビス(p−ヒドロキシフェニル)プロパン、2,2−ビス(p−ヒドロキシフェニル)プロパン(別名:ビスフェノールA又はBPA)、2,2−ビス(p−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、1,1−ビス(4−ヒドロキシフェニル)−1−フェニルエタン、2,2−ビス(4−ヒドロキシ−3−メチルフェニル)プロパン、2,2−ビス(3−フェニル−4−ヒドロキシフェニル)プロパン4,4’−シクロヘキシリデンジフェノール、2,2−ビス(3,5−ジブロム−4−ヒドロキシフェニル)プロパン(別名:テトラブロモビスフェノールA)、4,4’−イソプロピリデンビス(2−t−ブチルフェノール)、2,2’−メチレンビス(4−クロロフェノール)、4,4’−イソプロピリデンビス(o−メチルフェノール)、4,4’−セカンダリーブチリデンビスフェノール、4,4’−イソプロビリデンビス(2−クロロフェノール)、4,4’−ブチリデンビス(6−ターシャリーブチル−2−メチルフェノール)、4,4’−ジヒドロキシジフェニルスルホン、2,4’−ジヒドロキシジフェニルスルホン、4−イソプロポキシ−4’−ヒドロキシジフェニルスルホン、4−ヒドロキシ−4’−アリルオキシジフェニルスルホン、4−ベンジルオキシ−4’−ヒドロキシ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、4,4’−ジフェノールスルホキシド、p−ヒドロキシ安息香酸エチル、p−ヒドロキシ安息香酸イソプロピル、p−ヒドロキシ安息香酸ベンジル、プロトカテキユ酸ベンジル、没食子酸ステアリル、没食子酸ラウリル、没食子酸オクチル、4−ヒドロキシフタル酸ジベンジル、4−ヒドロキシフタル酸ジメチル、サリチルアニリド、5−クロロ−サリチルアニリド、ビス−(4−ヒドロキジフェニル)酢酸ブチルエステル、ビス−(4−ヒドロキシフェニル)酢酸ベンジルエステル、1,3−ビス(4−ヒドロキシクミル)ベンゼン、1,4−ビス(4−ヒドロキシクロル)ベンゼン、5−ヒドロキシイソフタル酸エチル、3,4−ジヒドロキシ−4’−メチルジフェニルスルホン、下記式(1)で表されるビスフェノール化合物、及び下記式(2)で表されるビスフェノールS誘導体から選ばれる。式(1)中、Rはメチル基及びエチル基等のアルキル基を示し、好ましくはメチル基である。 The phenol compound as the developer is a phenol resin formed from a phenol compound not containing 4-t-butylphenol and formaldehyde (for example, a phenol novolak resin formed from phenol and formaldehyde), bisphenol A, bisphenol S, etc. The bisphenol compound may be used. Examples of the phenol compound include α-naphthol, β-naphthol, p-octylphenol, 4-t-octylphenol, pt-butylphenol, p-phenylphenol, 1,1-bis (p-hydroxyphenyl) propane, 2, 2-bis (p-hydroxyphenyl) propane (also known as bisphenol A or BPA), 2,2-bis (p-hydroxyphenyl) butane, 1,1-bis (p-hydroxyphenyl) cyclohexane, 1,1-bis (4-hydroxyphenyl) -1-phenylethane, 2,2-bis (4-hydroxy-3-methylphenyl) propane, 2,2-bis (3-phenyl-4-hydroxyphenyl) propane 4,4′- Cyclohexylidene diphenol, 2,2-bis (3,5-dibromo-4-hydroxypheny ) Propane (also known as tetrabromobisphenol A), 4,4′-isopropylidenebis (2-t-butylphenol), 2,2′-methylenebis (4-chlorophenol), 4,4′-isopropylidenebis ( o-methylphenol), 4,4′-secondary butylidene bisphenol, 4,4′-isopropylidene bis (2-chlorophenol), 4,4′-butylidene bis (6-tertiarybutyl-2-methylphenol) 4,4′-dihydroxydiphenylsulfone, 2,4′-dihydroxydiphenylsulfone, 4-isopropoxy-4′-hydroxydiphenylsulfone, 4-hydroxy-4′-allyloxydiphenylsulfone, 4-benzyloxy-4 ′ -Hydroxydiphenylsulfone, bis (3-allyl-4- Droxyphenyl) sulfone, 4,4′-diphenol sulfoxide, ethyl p-hydroxybenzoate, isopropyl p-hydroxybenzoate, benzyl p-hydroxybenzoate, benzyl protocatechuate, stearyl gallate, lauryl gallate, gallic acid Octyl, 4-hydroxyphthalic acid dibenzyl, 4-hydroxyphthalic acid dimethyl, salicylanilide, 5-chloro-salicylanilide, bis- (4-hydroxydiphenyl) acetic acid butyl ester, bis- (4-hydroxyphenyl) acetic acid benzyl ester, 1,3-bis (4-hydroxycumyl) benzene, 1,4-bis (4-hydroxychloro) benzene, ethyl 5-hydroxyisophthalate, 3,4-dihydroxy-4′-methyldiphenylsulfone, 1) It is selected from a sphenol compound and a bisphenol S derivative represented by the following formula (2). In the formula (1), R represents an alkyl group such as a methyl group or an ethyl group, and is preferably a methyl group.
顕色剤としてのチオフェノール化合物は、例えば、4,4’−チオビスフェノール、4,4’−チオビス(6−ターシャリーブチル−2−メチルフェノール)、1,3−ビス(4−ヒドロキシフェニルチオ)−プロパン、及び1,8−ビス(4−ヒドロキシフェニルチオ)−2−ヒドロキシプロパンから選ばれる。 Examples of the thiophenol compound as the developer include 4,4′-thiobisphenol, 4,4′-thiobis (6-tertiarybutyl-2-methylphenol), 1,3-bis (4-hydroxyphenylthio). ) -Propane and 1,8-bis (4-hydroxyphenylthio) -2-hydroxypropane.
顕色剤としての尿素化合物は、例えば、尿素樹脂、及び下記式(3)で表されるスルホニルウレア化合物から選ばれる。 The urea compound as the developer is selected from, for example, a urea resin and a sulfonylurea compound represented by the following formula (3).
顕色剤としてのチオ尿素化合物は、例えば、N,N’−ジフェニルチオ尿素、及びN,N’−ジ(m−クロロフェニル)チオ尿素から選ばれる。 The thiourea compound as the developer is selected from, for example, N, N′-diphenylthiourea and N, N′-di (m-chlorophenyl) thiourea.
顕色剤としての有機酸金属塩は、例えば、1−アセチルオキシ−2−ナフトエ酸亜鉛、2−アセチルオキシ−1,ナフトエ酸亜鉛、2−アセチルオキシ−3−ナフトエ酸亜鉛、α,α−ビス(4−ヒドロキジフェニル)−α−メチルトルエン、チオシアン酸亜鉛のアンチピリン錯体、及び3,5−ジ(α−メチルベンジル)サリチル酸亜鉛塩から選ばれる。 Examples of the organic acid metal salt as the developer include zinc 1-acetyloxy-2-naphthoate, 2-acetyloxy-1, zinc naphthoate, zinc 2-acetyloxy-3-naphthoate, α, α- It is selected from bis (4-hydroxydiphenyl) -α-methyltoluene, an antipyrine complex of zinc thiocyanate, and 3,5-di (α-methylbenzyl) salicylic acid zinc salt.
顕色剤として用いられ得るその他の化合物として、例えば2,4’−ジフェニルスルホンがある。 Another compound that can be used as a developer is, for example, 2,4'-diphenylsulfone.
これら化合物は、単独で又は複数種を組み合わせて用いられる。 These compounds are used alone or in combination of two or more.
式(1)のビスフェノール化合物は、例えば、フェノールとグリオキシル酸とを酸性の反応液中で反応させて、下記式(1A)で示されるヒドロキシカルボン酸化合物を生成させる工程と、反応液を水と混合して得た水性液をアルカリ性に調整し、水性液から不純物を有機溶媒により抽出する工程と、水性液を酸性に調整し、水性液からヒドロキシカルボン酸化合物を有機溶媒により抽出する工程と、水性液から抽出されたヒドロキシカルボン酸化合物をエステル化して、式(1)で示されるビスフェノール化合物を生成させる工程と、をこの順に備える方法により得ることができる。 The bisphenol compound of formula (1) includes, for example, a step of reacting phenol and glyoxylic acid in an acidic reaction solution to produce a hydroxycarboxylic acid compound represented by the following formula (1A), Adjusting the aqueous liquid obtained by mixing to alkaline, extracting the impurities from the aqueous liquid with an organic solvent, adjusting the aqueous liquid to acidic, and extracting the hydroxycarboxylic acid compound from the aqueous liquid with an organic solvent; The step of esterifying the hydroxycarboxylic acid compound extracted from the aqueous liquid to produce the bisphenol compound represented by the formula (1) can be obtained by a method comprising in this order.
感熱発色層中の発色性化合物として用いられるロイコ染料は、一般に感圧記録紙又は感熱記録紙に用いられている化合物から、適宜選択することができる。ロイコ染料(発色性化合物)は、例えば、フルオラン系化合物、トリアリールメタン系化合物、スピロ系化合物、ジフェニルメタン系化合物、チアジン系化合物、ラクタム系化合物、及びフルオラン系化合物からなる群より選ばれる少なくとも1種の化合物である。 The leuco dye used as the color-forming compound in the heat-sensitive color developing layer can be appropriately selected from compounds generally used for pressure-sensitive recording paper or heat-sensitive recording paper. The leuco dye (color-forming compound) is, for example, at least one selected from the group consisting of a fluoran compound, a triarylmethane compound, a spiro compound, a diphenylmethane compound, a thiazine compound, a lactam compound, and a fluoran compound. It is a compound of this.
フルオラン系化合物としては、例えば3−ジエチルアミノ−6−メチル−7−アニリノフルオラン、3−ジブチルアミノ−6−メチル−7−アニリノフルオラン、3−ジペンチルアミノ−6−メチル−7−アニリノフルオラン、3−(N−メチル−N−シクロヘキシルアミノ)−6−メチル−7−アニリノフルオラン、3−(N−エチル−N−イソペンチルアミノ)−6−メチル−7−アニリノフルオラン、3−(N−エチル−N−イソブチルアミノ)−6−メチル−7−アニリノフルオラン、3−[N−エチル−N−(3−エトキシプロピル)アミノ]−6−メチル−7−アニリノフルオラン、3−(N−エチル−N−ヘキシルアミノ)−6−メチル−7−アニリノフルオラン、3−(N−メチル−N−プロピルアミノ)−6−メチル−7−アニリノフルオラン、3−(N−エチル−N−テトラヒドロフリルアミノ)−6−メチル−7−アニリノフルオラン、3−ジエチルアミノ−6−メチル−7−(p−クロロアニリノ)フルオラン、3−ジエチルアミノ−6−メチル−7−(p−フルオロアニリノ)フルオラン、3−[N−エチル−N−(p−トリル)アミノ]−6−メチル−7−アニリノフルオラン、3−ジエチルアミノ−6−メチ5ル−7−(p−トルイジノ)フルオラン、3−ジエチルアミノ−7−(o−クロロアニリノ)フルオラン、3−ジブチルアミノ−7−(o−クロロアニリノ)フルオラン、3−ジエチルアミノ−7−(o−フルオロアニリノ)フルオラン、3−ジブチルアミノ−7−(o−フルオロアニリノ)フルオラン、3−ジエチルアミノ−7−(3,4−ジクロロアニリノ)フルオラン、3−ピロリジノ−6−メチル−7−アニリノフルオラン、3−ジエチルアミノ−6−クロロ−7−エトキシエチルアミノフルオラン、3−ジエチルアミノ−6−クロロ−7−アニリノフルオラン、3−ジエチルアミノ−7−クロロフルオラン、3−ジエチルアミノ−7−メチルフルオラン、3−ジエチルアミノ−7−オクチルフルオラン、及び3−[N−エチル−N−(p−トリル)アミノ]−6−メチル−7−フェネチルフルオランが挙げられる。 Examples of the fluorane compound include 3-diethylamino-6-methyl-7-anilinofluorane, 3-dibutylamino-6-methyl-7-anilinofluorane, 3-dipentylamino-6-methyl-7-aniline. Linofluorane, 3- (N-methyl-N-cyclohexylamino) -6-methyl-7-anilinofluorane, 3- (N-ethyl-N-isopentylamino) -6-methyl-7-anilino Fluorane, 3- (N-ethyl-N-isobutylamino) -6-methyl-7-anilinofluorane, 3- [N-ethyl-N- (3-ethoxypropyl) amino] -6-methyl-7 -Anilinofluorane, 3- (N-ethyl-N-hexylamino) -6-methyl-7-anilinofluorane, 3- (N-methyl-N-propylamino) -6-methyl-7 Anilinofluorane, 3- (N-ethyl-N-tetrahydrofurylamino) -6-methyl-7-anilinofluorane, 3-diethylamino-6-methyl-7- (p-chloroanilino) fluorane, 3-diethylamino -6-methyl-7- (p-fluoroanilino) fluorane, 3- [N-ethyl-N- (p-tolyl) amino] -6-methyl-7-anilinofluorane, 3-diethylamino-6- Methyl-5- (p-toluidino) fluorane, 3-diethylamino-7- (o-chloroanilino) fluorane, 3-dibutylamino-7- (o-chloroanilino) fluorane, 3-diethylamino-7- (o-fluoro) Anilino) fluorane, 3-dibutylamino-7- (o-fluoroanilino) fluorane, 3-diethylamino-7- (3,4 Dichloroanilino) fluorane, 3-pyrrolidino-6-methyl-7-anilinofluorane, 3-diethylamino-6-chloro-7-ethoxyethylaminofluorane, 3-diethylamino-6-chloro-7-anilinofluor Oran, 3-diethylamino-7-chlorofluorane, 3-diethylamino-7-methylfluorane, 3-diethylamino-7-octylfluorane, and 3- [N-ethyl-N- (p-tolyl) amino]- 6-methyl-7-phenethylfluorane is mentioned.
トリアリールメタン系化合物としては、例えば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(別名:クリスタルバイオレットラクトン又はCVL)、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−ジメチルアミノインドール−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−フェニルインドール−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−(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、及び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が挙げられる。
Examples of triarylmethane compounds include 3,3-bis (p-dimethylaminophenyl) -6-dimethylaminophthalide (also known as crystal violet lactone or CVL), 3,3-bis (p-dimethylaminophenyl). Phthalide, 3- (p-dimethylaminophenyl) -3- (1,2-dimethylaminoindol-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-
スピロ系化合物としては、例えば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−プロピルスピロベンゾピラン、3−メチルナフト−(3−メトキシベンゾ)スピロピラン、及び1,3,3−トリメチル−6−ニトロ−8’−メトキシスピロ(インドリン−2,2’−ベンゾピラン)が挙げられる。 Examples of the spiro compound include 3-methylspirodinaphthopyran, 3-ethylspirodinaphthopyran, 3,3′-dichlorospirodinaphthopyran, 3-benzylspirodinaphthopyran, 3-propylspirodinaphthopyran, 3 -Methylnaphtho- (3-methoxybenzo) spiropyran and 1,3,3-trimethyl-6-nitro-8'-methoxyspiro (indoline-2,2'-benzopyran).
ジフェニルメタン系化合物としては、例えばN−ハロフェニル−ロイコオーラミン、4,4−ビス−ジメチルアミノフェニルベンズヒドリルベンジルエーテル、及びN−2,4,5−トリクロロフェニルロイコオーラミンが挙げられる。 Examples of the diphenylmethane compound include N-halophenyl-leucooramine, 4,4-bis-dimethylaminophenylbenzhydrylbenzyl ether, and N-2,4,5-trichlorophenylleucooramine.
チアジン系化合物としては、例えばベンゾイルロイコメチレンブルー、及びp−ニトロベンゾイルロイコメチレンブルーが挙げられる。 Examples of thiazine compounds include benzoyl leucomethylene blue and p-nitrobenzoyl leucomethylene blue.
ラクタム系化合物としては、例えばローダミンBアニリノラクタム、及びローダミンB−p−クロロアニリノラクタムが挙げられる。 Examples of the lactam compound include rhodamine B anilinolactam and rhodamine Bp-chloroanilinolactam.
フルオレン系化合物としては、例えば3,6−ビス(ジメチルアミノ)フルオレンスピロ(9,3’)−6’−ジメチルアミノフタリド、3,6−ビス(ジメチルアミノ)フルオレンスピロ(9,3’)−6’−ピロリジノフタリド、及び3−ジメチルアミノ−6−ジエチルアミノフルオレンスピロ(9,3’)−6’−ピロリジノフタリドが挙げられる。 Examples of the fluorene compound include 3,6-bis (dimethylamino) fluorene spiro (9,3 ′)-6′-dimethylaminophthalide and 3,6-bis (dimethylamino) fluorene spiro (9,3 ′). -6'-pyrrolidinophthalide and 3-dimethylamino-6-diethylaminofluorene spiro (9,3 ')-6'-pyrrolidinophthalide.
以上挙げたロイコ染料としての発色性化合物は、単独又は複数種を組み合わせて用いられる。 The chromogenic compounds as the leuco dyes mentioned above are used singly or in combination.
感熱発色層は、好ましくは結合剤を更に含有する。結合剤としては、水溶性化合物、又は水分散性化合物若しくはエマルションが用いられる。水溶性化合物は、例えば、メチルセルロース、エチルセルロース、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、アセチルセルロース、ポリビニルアルコール(PVA)、カルボキシル基変性ポリビニルアルコール、スルホン酸基変性ポリビニルアルコール、シリル基変性ポリビニルアルコール、ポリビニルピロリドン、ポリアクリルアミド、ポリアクリル酸、デンプン及びその誘導体、カゼイン、ゼラチン、水溶性イソプレンゴム、スチレン/無水マレイン酸共重合体、並びにイソ(又はジイソ)ブチレン/無水マレイン酸共重合体から選ばれる。水分散性化合物又はエマルションは、例えば、スチレン/ブタジエンラテックス、カルボキシル化スチレン/ブタジエンラテックス、アクリル酸エステル系共重合体、スチレン/アクリル酸系共重合体、エチレン/酢酸ビニル系共重合体、アクリル/ウレタン系共重合体、アクリル/ポリエステル系共重合体、及びアクリル/シリコン系共重合体から選ばれる。 The thermosensitive coloring layer preferably further contains a binder. As the binder, a water-soluble compound, a water-dispersible compound or an emulsion is used. Examples of the water-soluble compound include methyl cellulose, ethyl cellulose, methoxy cellulose, hydroxyethyl cellulose, carboxymethyl cellulose, acetyl cellulose, polyvinyl alcohol (PVA), carboxyl group-modified polyvinyl alcohol, sulfonic acid group-modified polyvinyl alcohol, silyl group-modified polyvinyl alcohol, and polyvinylpyrrolidone. , Polyacrylamide, polyacrylic acid, starch and derivatives thereof, casein, gelatin, water-soluble isoprene rubber, styrene / maleic anhydride copolymer, and iso (or diiso) butylene / maleic anhydride copolymer. Water dispersible compounds or emulsions include, for example, styrene / butadiene latex, carboxylated styrene / butadiene latex, acrylic acid ester copolymers, styrene / acrylic acid copolymers, ethylene / vinyl acetate copolymers, acrylic / It is selected from urethane copolymers, acrylic / polyester copolymers, and acrylic / silicon copolymers.
4−t−ブチルフェノールを含むフェノール化合物とホルムアルデヒドとから形成されるフェノールノボラック樹脂の量は、感熱発色層の質量を基準として、1〜50質量%、又は1〜30質量%であってもよい。ロイコ染料の量は、通常1〜50質量%であり、5〜30質量%であってもよい。顕色剤の量は、通常1〜70質量%であり、10〜50質量%であってもよい。感熱発色層中の結合剤の量は、通常1〜90質量%である。顕色剤のロイコ染料に対する質量比は、通常0.5〜20倍であり、1〜5倍であってもよい。各成分の量がこれら数値範囲内であることにより、本発明の効果がより顕著に奏される。 The amount of the phenol novolac resin formed from the phenolic compound containing 4-t-butylphenol and formaldehyde may be 1 to 50% by mass or 1 to 30% by mass based on the mass of the thermosensitive coloring layer. The amount of the leuco dye is usually 1 to 50% by mass and may be 5 to 30% by mass. The amount of the developer is usually 1 to 70% by mass and may be 10 to 50% by mass. The amount of the binder in the thermosensitive coloring layer is usually 1 to 90% by mass. The mass ratio of the developer to the leuco dye is usually 0.5 to 20 times and may be 1 to 5 times. When the amount of each component is within these numerical ranges, the effects of the present invention are more remarkably exhibited.
感熱発色層は、必要に応じて、増感剤、安定剤、充填剤、界面活性剤、及びその他の添加剤等を含んでいてもよい。増感剤、安定剤及び充填剤の量は、通常各々0〜80質量%である。界面活性剤及びその他の添加剤は、各々任意の割合、例えば通常各々0〜30質量%の範囲で感熱発色層に加えられる。 The heat-sensitive color forming layer may contain a sensitizer, a stabilizer, a filler, a surfactant, and other additives as necessary. The amount of the sensitizer, stabilizer and filler is usually 0 to 80% by mass. The surfactant and other additives are each added to the thermosensitive coloring layer in an arbitrary ratio, for example, usually in the range of 0 to 30% by mass.
増感剤は、常温で固体であり、融点を有することが好ましく。増感剤の融点は好ましくは約70℃以上である。増感剤としては、例えば動植物性ワックス、合成ワックスなどのワックスや高級脂肪酸、高級脂肪酸アミド、高級脂肪酸アニリド、ナフタレン誘導体、芳香族エーテル、芳香族カルボン酸誘導体、芳香族スルホン酸エステル誘導体、炭酸又はシュウ酸ジエステル誘導体、ビフェニル誘導体、ターフェニル誘導体、スルホン誘導体が用いられる。 The sensitizer is preferably solid at room temperature and has a melting point. The melting point of the sensitizer is preferably about 70 ° C or higher. Examples of the sensitizer include waxes such as animal and vegetable waxes and synthetic waxes, higher fatty acids, higher fatty acid amides, higher fatty acid anilides, naphthalene derivatives, aromatic ethers, aromatic carboxylic acid derivatives, aromatic sulfonic acid ester derivatives, carbonic acid or Oxalic acid diester derivatives, biphenyl derivatives, terphenyl derivatives, and sulfone derivatives are used.
ワックスとしては、例えば木蝋、カルナウバ蝋、シェラック、パラフィン、モンタン蝋、酸化パラフィン、ポリエチレンワックス、酸化ポリエチレンが挙げられる。高級脂肪酸としては、例えばステアリン酸、ベヘン酸が挙げられる。高級脂肪酸アミドとしては、例えばステアリン酸アミド、オレイン酸アミド、N−メチルステアリン酸アミド、エルカ酸アミド、メチロールベヘン酸アミド、メチレンビスステアリン酸アミド、エチレンビスステアリン酸アミドが挙げられる。高級脂肪酸アニリドとしては、例えばステアリン酸アニリド、リノール酸アニリドが挙げられる。ナフタレン誘導体の具体例としては、例えば1−ベンジルオキシナフタレン、2−ベンジルオキシナフタレン、1−ヒドロキシナフトエ酸フェニルエステル等が挙げられる。芳香族エーテルとしては、例えば1,2−ジフェノキシエタン、1,4−ジフェノキシブタン、1,2−ビス(3−メチルフェノキシ)エタン、1,2−ビス(4−メトキシフェノキシ)エタン、1,2−ビス(3,4−ジメチルフェニル)エタン、1−フェノキシ−2−(4−クロロフェノキシ)エタン、1−フェノキシ−2−(4−メトキシフェノキシ)エタン、1,2−ジフェノキシメチルベンゼンが挙げられる。芳香族カルボン酸誘導体としては、例えば、p−ベンジルオキシ安息香酸ベンジルエステル、テレフタル酸ジベンジルエステルが挙げられる。芳香族スルホン酸エステル誘導体としては、例えばp−トルエンスルホン酸フェニルエステル、フェニルメシチレンスルホナート、4−メチルフェニルメシチレンスルホナートが挙げられる。炭酸又はシュウ酸ジエステル誘導体としては、例えば炭酸ジフェニル、シュウ酸ジベンジル、シュウ酸ジ(4−クロロベンジル)、シュウ酸ジ(4−メチルベンジル)が挙げられる。ビフェニル誘導体としては、例えばp−ベンジルビフェニル、p−アセチルビフェニル、p−アリルオキシビフェニルが挙げられる。ターフェニル誘導体としては、例えばm−ターフェニル、ターフェニル異性体混合物等が挙げられる。スルホン誘導体としては、例えばジフェニルスルホン、4−メチルジフェニルスルホン、塩素化ジフェニルスルホンが挙げられる。これらの増感剤は、これらの中から一種又は二種以上を適宜選択して、所望により使用される。 Examples of the wax include wood wax, carnauba wax, shellac, paraffin, montan wax, oxidized paraffin, polyethylene wax, and oxidized polyethylene. Examples of higher fatty acids include stearic acid and behenic acid. Examples of the higher fatty acid amide include stearic acid amide, oleic acid amide, N-methyl stearic acid amide, erucic acid amide, methylol behenic acid amide, methylene bis stearic acid amide, and ethylene bis stearic acid amide. Examples of the higher fatty acid anilide include stearic acid anilide and linoleic acid anilide. Specific examples of naphthalene derivatives include 1-benzyloxynaphthalene, 2-benzyloxynaphthalene, 1-hydroxynaphthoic acid phenyl ester, and the like. Examples of the aromatic ether include 1,2-diphenoxyethane, 1,4-diphenoxybutane, 1,2-bis (3-methylphenoxy) ethane, 1,2-bis (4-methoxyphenoxy) ethane, 1 , 2-bis (3,4-dimethylphenyl) ethane, 1-phenoxy-2- (4-chlorophenoxy) ethane, 1-phenoxy-2- (4-methoxyphenoxy) ethane, 1,2-diphenoxymethylbenzene Is mentioned. Examples of the aromatic carboxylic acid derivative include p-benzyloxybenzoic acid benzyl ester and terephthalic acid dibenzyl ester. Examples of the aromatic sulfonic acid ester derivative include p-toluenesulfonic acid phenyl ester, phenyl mesitylene sulfonate, and 4-methylphenyl mesitylene sulfonate. Examples of the carbonic acid or oxalic acid diester derivative include diphenyl carbonate, dibenzyl oxalate, di (4-chlorobenzyl) oxalate, and di (4-methylbenzyl) oxalate. Examples of the biphenyl derivative include p-benzylbiphenyl, p-acetylbiphenyl, and p-allyloxybiphenyl. Examples of the terphenyl derivative include m-terphenyl and a terphenyl isomer mixture. Examples of the sulfone derivative include diphenyl sulfone, 4-methyldiphenyl sulfone, and chlorinated diphenyl sulfone. These sensitizers are appropriately used by selecting one or two or more of these sensitizers.
安定剤として、例えば、酸化防止若しくは老化防止効果を付与するフェノール誘導体及びアミン誘導体、又は、紫外線吸収剤としてのベンゾトリアゾール系化合物及びベンゾフェノン系化合物が使用できる。 As the stabilizer, for example, a phenol derivative and an amine derivative imparting an antioxidant or antiaging effect, or a benzotriazole compound and a benzophenone compound as an ultraviolet absorber can be used.
フェノール誘導体及びアミン誘導体としては、例えば、2,2’−メチレンビス(4−メチル−6−tーブチルフェノール)、2,2’−メチレンビス(4−エチル−6−t−ブチルフェノール)、4,4’−ブチリデンビス(6−t−ブチル−2−メチルフェノール)、4,4’−チオビス(6−t−ブチル−2−メチルフェノール)、1,1,3−トリス(2−メチル−4−ヒドロキシ−5−t−ブチルフェニル)ブタン、1,1,3−トリス(2−メチル−4−ヒドロキシ−5−シクロヘキシルフェニル)ブタン、テトラメチルビスフェノールS、テトラブロモビスフェノールS、4,4’−チオビス(2−メチルフェノール)、4,4’−チオビス(2−クロロフェノール)、セバシン酸ビス(2,2,6,6−テトラメチル−4−ピペリジニル)、テトラキス(1,2,2,6,6−ペンタメチル−4−ピペリジル)−1,2,3,4−ブタンテトラカルボキシレート、テトラキス(1,2,2,6,6−テトラメチル−4−ピペリジル)−1,2,3,4−ブタンテトラカルボキシレートが挙げられる。 Examples of phenol derivatives and amine derivatives include 2,2′-methylenebis (4-methyl-6-tert-butylphenol), 2,2′-methylenebis (4-ethyl-6-tert-butylphenol), 4,4 ′. -Butylidenebis (6-t-butyl-2-methylphenol), 4,4'-thiobis (6-t-butyl-2-methylphenol), 1,1,3-tris (2-methyl-4-hydroxy-) 5-t-butylphenyl) butane, 1,1,3-tris (2-methyl-4-hydroxy-5-cyclohexylphenyl) butane, tetramethylbisphenol S, tetrabromobisphenol S, 4,4′-thiobis (2 -Methylphenol), 4,4′-thiobis (2-chlorophenol), bis (2,2,6,6-tetramethyl-4-sebacate) Peridinyl), tetrakis (1,2,2,6,6-pentamethyl-4-piperidyl) -1,2,3,4-butanetetracarboxylate, tetrakis (1,2,2,6,6-tetramethyl-) 4-piperidyl) -1,2,3,4-butanetetracarboxylate.
ベンゾトリアゾール系化合物としては、例えば2−(2’−ヒドロキシ−5’−メチル−フェニル)−ベンゾトリアゾール、2−(2’−ヒドロキシ−3’,5’−ジ−t−ブチルフェニル)−5−クロロベンゾトリアゾール、2−(2′−ヒドロキシ−3′−t−ブチル−5′−メチルフェニル)−5−クロロベンゾトリアゾール、2−(2’−ヒドロキシ−5’−t−オクチルフェニル)−ベンゾトリアゾール、2−(2’−ヒドロキシ−4’−オクトキシフェニル)−ベンゾトリアゾール、2−(2’−ヒドロキシ−3’,5’−ジ−t−ブチルフェニル)−ベンゾトリアゾール、2−(2’−ヒドロキシ−3’,5’−ジ−t−アミルフェニル)−ベンゾトリアゾール、メチレン−ビス[2−(2’−ヒドロキシ−5’−ドデカニルフェニル)ベンゾトリアゾール]が挙げられる。 Examples of the benzotriazole compounds include 2- (2′-hydroxy-5′-methyl-phenyl) -benzotriazole and 2- (2′-hydroxy-3 ′, 5′-di-t-butylphenyl) -5. -Chlorobenzotriazole, 2- (2'-hydroxy-3'-t-butyl-5'-methylphenyl) -5-chlorobenzotriazole, 2- (2'-hydroxy-5'-t-octylphenyl)- Benzotriazole, 2- (2′-hydroxy-4′-octoxyphenyl) -benzotriazole, 2- (2′-hydroxy-3 ′, 5′-di-t-butylphenyl) -benzotriazole, 2- ( 2′-hydroxy-3 ′, 5′-di-t-amylphenyl) -benzotriazole, methylene-bis [2- (2′-hydroxy-5′-dodecanyl phen Le) benzotriazole], and the like.
ベンゾフェノン系化合物としては、例えば2,4−ジヒドロキシベンゾフェノン、2−ヒドロキシ−4−メトキシベンゾフェノン、2,2’−ジヒドロキシ−4,4’−メトキシベンゾフェノン、2−ヒドロキシ−4−メトキシ−5−スルホベンゾフェノン、ビス(2−メトキシ−4−ヒドロキシ−5−ベンゾイルフェニルメタンが挙げられる。 Examples of the benzophenone compounds include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2,2′-dihydroxy-4,4′-methoxybenzophenone, 2-hydroxy-4-methoxy-5-sulfobenzophenone. Bis (2-methoxy-4-hydroxy-5-benzoylphenylmethane).
充填剤としては、例えば炭酸カルシウム、シリカ、ホワイトカーボン、タルク、クレー、アルミナ、酸化チタン、酸化亜鉛、水酸化アルミニウム、酸化アルミニウム、炭酸マグネシウム、酸化マグネシウム、水酸化マグネシウム、硫酸バリウム、ポリスチレン樹脂、尿素−ホルマリン樹脂、中空プラスチック顔料、発泡性中空プラスチック顔料が挙げられる。 Examples of the filler include calcium carbonate, silica, white carbon, talc, clay, alumina, titanium oxide, zinc oxide, aluminum hydroxide, aluminum oxide, magnesium carbonate, magnesium oxide, magnesium hydroxide, barium sulfate, polystyrene resin, urea -Formalin resin, hollow plastic pigment, foamable hollow plastic pigment.
界面活性剤としては、例えば、脂肪酸の金属石鹸類、ポリカルボン酸型高分子活性剤類、高級アルコールの硫酸エステル塩類、アルキルポリエーテルの硫酸エステル塩類、高級アルコールのエチレンオキサイド付加物類、アルキルアリールスルホン酸塩類、アルキルスルホン酸類、アリールスルホン酸類、リン酸エステル類、脂肪族リン酸エステル類、芳香族リン酸エステル類、ポリオキシエチレンアルキル硫酸エステル類、ポリオキシエチレンアリール硫酸エステル類、ポリオキシエチレンアルキルアリール硫酸エステル類、ジアルキルスルホコハク酸エステル類、アルキルベンゼンスルホン酸塩類、ポリオキシアルキレンアルキルエーテルリン酸エステル、ポリオキシアルキレンアリールエーテルリン酸エステル、ポリオキシアルキレンアルキルアリールエーテルリン酸エステル、アルキル硫酸ナトリウム、スルホコハク酸ジオクチルナトリウム塩、ポリアルキレングリコー9ル(例えば、ポリオキシエチレンノニルフェニルエーテル)、アセチレングリコール、アセチレングリコールのエチレンオキサイド付加物、アセチレングリコールのプロピレンオキサイド付加物、アセチレングリコールのエチレンオキサイド及びプロピレンオキサイド付加物等が挙げられる。 Surfactants include, for example, fatty acid metal soaps, polycarboxylic acid type polymer activators, sulfates of higher alcohols, sulfates of alkyl polyethers, ethylene oxide adducts of higher alcohols, alkylaryls. Sulfonates, alkyl sulfonic acids, aryl sulfonic acids, phosphate esters, aliphatic phosphate esters, aromatic phosphate esters, polyoxyethylene alkyl sulfate esters, polyoxyethylene aryl sulfate esters, polyoxyethylene Alkylaryl sulfates, dialkylsulfosuccinates, alkylbenzenesulfonates, polyoxyalkylene alkyl ether phosphates, polyoxyalkylene aryl ether phosphates, polyoxyalkylenes Alkyl aryl ether phosphate, sodium alkyl sulfate, dioctyl sulfosuccinate sodium salt, polyalkylene glycol 9 (eg, polyoxyethylene nonylphenyl ether), acetylene glycol, ethylene oxide adduct of acetylene glycol, propylene oxide addition of acetylene glycol Products, ethylene oxide and propylene oxide adducts of acetylene glycol, and the like.
その他の添加物としては、滑剤(例えばテアリン酸亜鉛、ステアリン酸カルシウム等の高級脂肪酸金属塩)、耐水化剤(例えばグリオキサール、グルタルアルデヒド、ジアルデヒド、エチレンジアミン、尿素−ホルムアルデヒド樹脂、メラミン−ホルムアルデヒド樹脂、ポリアミド樹脂、ポリアミドアミン−エピクロロヒドリン樹脂、アジピン酸ジヒドラジド、フタル酸ジヒドラジド、ホウ酸、ホウ砂、乳酸チタン、炭酸ジルコニウムアンモニウム、および炭酸ジルコニウムカリウム)、増粘剤(例えばキサンタンガム、カルボキシメチルセルロース)、消泡剤及び抑泡剤(例えばシリコンオイル、鉱物油)、蛍光増白剤、蛍光染料、着色染料、着色顔料等が用いられ得る。 Other additives include lubricants (for example, higher fatty acid metal salts such as zinc stearate and calcium stearate), water resistance agents (for example, glyoxal, glutaraldehyde, dialdehyde, ethylenediamine, urea-formaldehyde resin, melamine-formaldehyde resin, polyamide) Resin, polyamidoamine-epichlorohydrin resin, adipic acid dihydrazide, phthalic acid dihydrazide, boric acid, borax, titanium lactate, ammonium zirconium carbonate and potassium zirconium carbonate), thickener (eg xanthan gum, carboxymethylcellulose), Foaming agents and antifoaming agents (for example, silicon oil, mineral oil), fluorescent whitening agents, fluorescent dyes, colored dyes, colored pigments and the like can be used.
感熱発色層は、例えば、ロイコ染料、顕色剤及び上記フェノールノボラック樹脂を、それぞれ別々に、結合剤及び必要に応じて増感剤、安定剤、充填剤、その他の添加剤等と共に、水等の媒体を用いて湿式粉砕して各成分が分散した分散液を調製する工程と、各分散液を混合して塗布液を調製する工程と、この塗布液を中間層上に塗布し、塗布された塗布液を乾燥する工程とを含む方法により形成することができる。上記分散液を得るための湿式分散は、ボールミル、アトライター、サンドミルなどの分散機を用いて行うことができる。感熱発色層の乾燥質量は、通常2〜20g/m2であり、4〜10g/m2であってもよい。The thermosensitive coloring layer is, for example, a leuco dye, a developer, and the phenol novolak resin, separately with a binder and, if necessary, a sensitizer, a stabilizer, a filler, other additives, etc. A step of preparing a dispersion liquid in which each component is dispersed by wet pulverization using the above medium, a step of preparing a coating liquid by mixing the respective dispersion liquids, and applying and applying the coating liquid on the intermediate layer. And a step of drying the applied coating solution. The wet dispersion for obtaining the dispersion liquid can be performed using a disperser such as a ball mill, an attritor or a sand mill. The dry mass of the thermosensitive coloring layer is usually 2 to 20 g / m 2 and may be 4 to 10 g / m 2 .
中間層5は、発泡体であってもよいし、中間層5中に分散する微小な中空粒子を含有していてもよい。また、中間層5は、中空粒子を含有する発泡体であってもよい。
The
中空粒子(微小中空フィラー)は、内部に空隙が形成されている粒子であり、例えば、プラスチック、ガラス又はセラミックから形成される。中空粒子を形成する材料は、好ましくはプラスチックであり、その中でも特に好ましくは熱可塑性樹脂である。 Hollow particles (fine hollow fillers) are particles in which voids are formed, and are formed of, for example, plastic, glass, or ceramic. The material forming the hollow particles is preferably a plastic, and among them, a thermoplastic resin is particularly preferable.
中空粒子は球状であることが好ましい。中空粒子の平均粒径は、通常0.2〜10μm、好ましくは0.5〜3μmである。中空粒子の中空率(みかけの体積に対する内部の空隙の割合)は大きい程、断熱効果が大きくなるために好ましい。ただし、粒子径によって、中空率が制限される場合がある。中空粒子の中空率は、好ましくは30〜90体積%、より好ましくは50〜90体積%である。 The hollow particles are preferably spherical. The average particle diameter of the hollow particles is usually 0.2 to 10 μm, preferably 0.5 to 3 μm. The larger the hollow ratio of hollow particles (the ratio of internal voids to the apparent volume), the greater the heat insulation effect, which is preferable. However, the hollow ratio may be limited depending on the particle diameter. The hollow ratio of the hollow particles is preferably 30 to 90% by volume, more preferably 50 to 90% by volume.
中間層に含まれる中空粒子の量は、中間層の質量を基準として、通常10〜90質量%、好ましくは40〜80質量%である。 The amount of the hollow particles contained in the intermediate layer is usually 10 to 90% by mass, preferably 40 to 80% by mass, based on the mass of the intermediate layer.
中間層としての発泡体は、例えば、熱可塑性樹脂からなる殻を有し、その内部に低沸点溶媒を発泡剤として含有する発泡性中空粒子を発泡させることにより形成される。 The foam as the intermediate layer is formed, for example, by foaming foamable hollow particles having a shell made of a thermoplastic resin and containing therein a low boiling point solvent as a foaming agent.
中間層は、結合剤、充填剤、安定剤、分散剤、消泡剤及びその他の添加剤から選ばれる他の成分を含んでいてもよい。これらの成分は、一般に感圧記録紙や感熱記録紙に用いられているものから適宜選択することが可能であり、例えば、後述の感熱発色層と同様の材料が用いられる。 The intermediate layer may contain other components selected from binders, fillers, stabilizers, dispersants, antifoaming agents and other additives. These components can be appropriately selected from those generally used for pressure-sensitive recording paper and heat-sensitive recording paper. For example, the same materials as those for a heat-sensitive coloring layer described later are used.
通常、結合剤の量は10〜50質量%で、充填剤の量は10〜50質量%である。必要に応じて加えられる安定剤、界面活性剤、その他の添加剤は任意の割合で、例えば通常各々0〜30質量%の範囲でそれぞれ中間層に加えられる。 Usually, the amount of binder is 10-50% by weight and the amount of filler is 10-50% by weight. Stabilizers, surfactants, and other additives that are added as necessary are added to the intermediate layer in arbitrary proportions, for example, usually in the range of 0 to 30% by mass.
中間層は、例えば、中空粒子、結合剤及び充填剤と、必要に応じて界面活性剤及びその他の添加剤とを水に混合及び分散して中間層用の塗布液を調製し、この塗布液を支持体上に塗布し、塗膜を乾燥することによって、形成される。中間層の乾燥質量は、通常は2〜20g/m2、好ましくは5〜10g/m2である。中間層用の塗布液は、バーコーター、ドクターブレード、グラビアコーター等を使って塗布することができる。The intermediate layer is prepared by, for example, mixing and dispersing hollow particles, a binder and a filler, and if necessary, a surfactant and other additives in water to prepare a coating solution for the intermediate layer. Is formed on the support and the coating film is dried. The dry mass of the intermediate layer is usually 2 to 20 g / m 2 , preferably 5 to 10 g / m 2 . The coating solution for the intermediate layer can be applied using a bar coater, a doctor blade, a gravure coater or the like.
発泡体である中間層は、例えば、発泡性中空粒子、結合剤及び充填剤と、必要に応じて界面活性剤及びその他の添加剤とを水に混合及び分散して中間層用の塗布液を調製する。この塗布液を支持体上に塗布し、塗膜を乾燥し、更に発泡処理を行って、形成される。発泡処理は、例えば、塗膜を、ヒーターを有するドラムドラーヤー等の表面に密着させ、発泡性中空粒子の殻を形成する熱可塑性樹脂が軟化する温度(100〜150℃)に加熱することにより行われる。 The intermediate layer which is a foam is prepared by mixing and dispersing, for example, expandable hollow particles, a binder and a filler, and, if necessary, a surfactant and other additives in water to form a coating solution for the intermediate layer. Prepare. The coating liquid is applied onto a support, the coating film is dried, and further foamed to form. The foaming treatment is performed, for example, by bringing the coating film into close contact with the surface of a drum dryer having a heater and heating to a temperature (100 to 150 ° C.) at which the thermoplastic resin forming the foamed hollow particle shell is softened. Done.
本実施形態に係る感熱記録材料は、必要に応じて、上記の中間層及び感熱発色層以外の層を更に備えていてもよい。例えば、中間層と感熱発色層の間に、さらに別の中間層が設けられてもよいし、感熱発色層上にオーバーコート層が設けられてもよい。別の中間層及びオーバーコート層は、例えば、上述のような結合剤及び充填剤と、必要に応じて加えられるその他の添加物とを含有する。これらの追加の層は、中間層及び感熱発色層と同様に、各成分を含む塗布液を、塗布し、これを乾燥することにより形成することができる。 The heat-sensitive recording material according to the present embodiment may further include a layer other than the intermediate layer and the heat-sensitive color forming layer as necessary. For example, another intermediate layer may be provided between the intermediate layer and the thermosensitive coloring layer, or an overcoat layer may be provided on the thermosensitive coloring layer. Another intermediate layer and overcoat layer contain, for example, binders and fillers as described above, and other additives added as needed. These additional layers can be formed by applying a coating solution containing each component and drying it, as in the case of the intermediate layer and the thermosensitive coloring layer.
オーバーコート層は、例えば、結合剤、充填剤及び滑剤と、必要に応じて加えられる界面活性剤、耐水化剤及びその他の添加剤とを含む。オーバーコート層の乾燥質量は、通常1〜10g/m2である。The overcoat layer includes, for example, a binder, a filler, and a lubricant, and a surfactant, a water resistant agent and other additives which are added as necessary. The dry mass of the overcoat layer is usually 1 to 10 g / m 2 .
以下、実施例を挙げて本発明についてさらに具体的に説明する。ただし、本発明はこれら実施例に限定されるものではない。 Hereinafter, the present invention will be described more specifically with reference to examples. However, the present invention is not limited to these examples.
1.中間層の形成
下記材料を混合して、中間層用の塗布液を調製した。この塗布液を、坪量が64g/m2の上質紙上に塗布し、塗膜を乾燥して、7g/m2の中間層を形成した。
30%中空微粒子水分散液(材質=スチレン/アクリル酸エステル共重合体、平均粒径=1μm、中空率=54%) 640部
60%炭酸カルシウム水分散液 50部
48%カルボキシル基変性SBRラテックス 85部
水 225部1. Formation of Intermediate Layer The following materials were mixed to prepare a coating solution for the intermediate layer. This coating solution was applied onto fine paper having a basis weight of 64 g / m 2 , and the coating film was dried to form an intermediate layer of 7 g / m 2 .
30% hollow fine particle aqueous dispersion (material = styrene / acrylic acid ester copolymer, average particle size = 1 μm, hollow ratio = 54%) 640 parts 60% calcium carbonate aqueous dispersion 50 parts 48% carboxyl group-modified SBR latex 85 225 parts water
2.感熱発色層の形成
下記材料を含む3種の混合物中の固形分を、ビーズミルを用いてその平均粒径が1μmになるまで粉砕しながら分散させて、[A]液、[B]液及び[C]液を得た。
[A]液(ロイコ染料)
3−ジブチルアミノ−6−メチル−7−アニリノフルオラン 30部
ポリビニルアルコール(PVA) 5部
水 65部
[B]液(顕色剤)
ビスフェノールA(BPA) 30部
ポリビニルアルコール(PVA) 5部
水 65部
[C]液(顕色助剤)
4−t−ブチルフェノール及びフェノールとホルムアルデヒドとから形成されたフェノール樹脂(ショウノールCKP−963P、昭和電工株式会社製)
30部
ポリビニルアルコール(PVA) 5部
水 65部2. Formation of thermosensitive coloring layer The solids in the three kinds of mixture containing the following materials were dispersed while being pulverized using a bead mill until the average particle size became 1 μm, and the [A] liquid, [B] liquid and [ C] solution was obtained.
[A] Liquid (leuco dye)
3-dibutylamino-6-methyl-7-anilinofluorane 30 parts polyvinyl alcohol (PVA) 5 parts water 65 parts [B] solution (developer)
Bisphenol A (BPA) 30 parts Polyvinyl alcohol (PVA) 5 parts Water 65 parts [C] solution (development aid)
4-t-butylphenol and phenol resin formed from phenol and formaldehyde (Shonol CKP-963P, Showa Denko KK)
30 parts polyvinyl alcohol (PVA) 5 parts water 65 parts
次いで、上記[A]液、[B]液及び[C]液を含む下記組成を有する感熱発色層用の塗布液を調製した。この塗布液を、上記中間層上に塗布し、塗膜を乾燥して、6g/m2の感熱発色層を形成して、上質紙、中間層及び感熱発色層から構成される感熱記録材料を得た。
[A]液 50部
[B]液 100部
[C]液 100部
60%炭酸カルシウム水分散液 83部
20%シリカ水分散液 250部
36%ステアリン酸亜鉛水分散液 61部
10%完全鹸化型PVA水溶液 200部
水 156部Next, a coating solution for a thermosensitive coloring layer having the following composition containing the [A] solution, [B] solution and [C] solution was prepared. The coating solution is applied onto the intermediate layer, and the coating film is dried to form a thermosensitive coloring layer of 6 g / m 2 , and a thermosensitive recording material composed of fine paper, the intermediate layer, and the thermosensitive coloring layer is obtained. Obtained.
[A] liquid 50 parts [B] liquid 100 parts [C] liquid 100 parts 60% calcium carbonate aqueous dispersion 83 parts 20% silica aqueous dispersion 250 parts 36% zinc stearate aqueous dispersion 61
[C]液を配合しない、又は[C]液の顕色助剤をビスフェノールS誘導体に変更して塗布液を調製し、上記と同様に感熱発色層を形成させて、感熱記録材料を得た。さらに、[B]液の顕色剤をビスフェノールS(BPS)、4−ヒドロキシ−4’−イソプロポキシジフェニルスルホン、又は下記式(10)で表されるビスフェノール化合物(MBHA)に変更して、同様に感熱記録材料を作成した。 [C] The liquid was not blended, or the coating aid was prepared by changing the color developing aid of the [C] liquid to a bisphenol S derivative, and a thermosensitive coloring layer was formed in the same manner as above to obtain a thermosensitive recording material. . Furthermore, the developer of the [B] solution was changed to bisphenol S (BPS), 4-hydroxy-4′-isopropoxydiphenyl sulfone, or a bisphenol compound (MBHA) represented by the following formula (10), and the same A heat sensitive recording material was prepared.
3.評価(耐熱性)
画像を形成させてから、各感熱記録材料を90℃の恒温器中に24時間放置する耐熱性試験を行った。試験前後の画像部及び地肌部の反射濃度(マクベス反射濃度)を、マクベス反射濃度計(SpectroEyeLT、サカタエンジニアリング(株)製)を用いて測定した。
(耐光性)
画像を形成させてから、各感熱記録材料に対して蛍光灯により5000ルクスの光を100時間照射する耐光性試験を行った。試験前後の画像部及び地肌部の反射濃度(マクベス反射濃度)を、マクベス反射濃度計を用いて測定した。
(耐水性)
画像を形成させてから、各感熱記録材料を25℃の水道水に24時間曝す耐水性試験を行った。試験前後の画像部及び地肌部の反射濃度(マクベス反射濃度)を、マクベス反射濃度計を用いて測定した。3. Evaluation (heat resistance)
After the image was formed, each heat-sensitive recording material was subjected to a heat resistance test in which it was left in a thermostat at 90 ° C. for 24 hours. The reflection density (Macbeth reflection density) of the image part and the background part before and after the test was measured using a Macbeth reflection densitometer (SpectroEyeLT, manufactured by Sakata Engineering Co., Ltd.).
(Light resistance)
After the image was formed, each heat-sensitive recording material was subjected to a light resistance test in which light of 5000 lux was irradiated for 100 hours with a fluorescent lamp. The reflection density (Macbeth reflection density) of the image part and the background part before and after the test was measured using a Macbeth reflection densitometer.
(water resistant)
After the image was formed, a water resistance test was performed in which each heat-sensitive recording material was exposed to tap water at 25 ° C. for 24 hours. The reflection density (Macbeth reflection density) of the image part and the background part before and after the test was measured using a Macbeth reflection densitometer.
測定結果を表1及び表2に示す。残存率は、試験後の反射濃度の試験前の反射濃度に対する比率である。 The measurement results are shown in Tables 1 and 2. The residual ratio is a ratio of the reflection density after the test to the reflection density before the test.
表に示す結果から、顕色助剤として4−t−ブチルフェノール及びフェノールとホルムアルデヒドとから形成れたフェノール樹脂(963P)を用いた感熱記録材料は、耐光性試験において、顕色助剤としてビスフェノールS誘導体を用いた場合と比較しても画像部の濃度がより良好に維持されるとともに、地肌部の発色が効果的に抑えらることが確認された。また、耐熱性及び耐水性についても、実用的に十分なレベルが維持された。 From the results shown in the table, a heat-sensitive recording material using 4-t-butylphenol and a phenol resin (963P) formed from phenol and formaldehyde as a color development aid is bisphenol S as a color development aid in a light resistance test. It was confirmed that the density of the image area was maintained better than the case where the derivative was used, and the color development of the background area was effectively suppressed. Moreover, practically sufficient level was maintained also about heat resistance and water resistance.
1…支持体、3…感熱発色層、5…中間層、7…オーバーコート層、10…感熱記録材料。 DESCRIPTION OF SYMBOLS 1 ... Support body, 3 ... Thermal coloring layer, 5 ... Intermediate | middle layer, 7 ... Overcoat layer, 10 ... Thermal recording material.
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JPS511436B2 (en) * | 1971-10-30 | 1976-01-17 | ||
JPS5317347A (en) * | 1976-07-31 | 1978-02-17 | Mitsubishi Paper Mills Ltd | Heat sensitive recording paper of which long period image stability is improved |
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