JP7413090B2

JP7413090B2 - 感熱記録体

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Publication number: JP7413090B2
Authority: JP; Japan
Prior art keywords: heat; sensitive recording; copolymer; group; monomer
Prior art date: 2020-03-06
Legal status : Active

Application number

JP2020038886A

Other languages

English (en)

Japanese (ja)

Other versions

JP2021138083A5 (enExample

JP2021138083A (ja

Inventor

健二平井

賢太郎川▲崎▼

佳美緑川

佑香村田

Current Assignee

Nippon Paper Industries Co Ltd

Original Assignee

Nippon Paper Industries Co Ltd

Priority date

2020-03-06

Filing date

2020-03-06

Publication date

2024-01-15

2020-03-06 Application filed by Nippon Paper Industries Co Ltd filed Critical Nippon Paper Industries Co Ltd

2020-03-06 Priority to JP2020038886A priority Critical patent/JP7413090B2/ja

2020-12-08 Priority to EP20900008.2A priority patent/EP4056605A4/en

2020-12-08 Priority to US17/784,584 priority patent/US12053997B2/en

2020-12-08 Priority to PCT/JP2020/045602 priority patent/WO2021117702A1/ja

2020-12-08 Priority to CN202080085525.3A priority patent/CN114786957B/zh

2021-09-16 Publication of JP2021138083A publication Critical patent/JP2021138083A/ja

2022-01-14 Publication of JP2021138083A5 publication Critical patent/JP2021138083A5/ja

2024-01-15 Application granted granted Critical

2024-01-15 Publication of JP7413090B2 publication Critical patent/JP7413090B2/ja

Status Active legal-status Critical Current

2040-03-06 Anticipated expiration legal-status Critical

Links

239000000463 material Substances 0.000 title claims description 40
239000000178 monomer Substances 0.000 claims description 98
239000010410 layer Substances 0.000 claims description 58
-1 polyoxyethylene chain Polymers 0.000 claims description 54
239000000839 emulsion Substances 0.000 claims description 50
239000011241 protective layer Substances 0.000 claims description 43
229920000178 Acrylic resin Polymers 0.000 claims description 37
239000004925 Acrylic resin Substances 0.000 claims description 37
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 32
229920001577 copolymer Polymers 0.000 claims description 30
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 20
125000005370 alkoxysilyl group Chemical group 0.000 claims description 19
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 16
QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 10
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 9
239000011258 core-shell material Substances 0.000 claims description 8
239000004094 surface-active agent Substances 0.000 claims description 8
230000000379 polymerizing effect Effects 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
239000002245 particle Substances 0.000 claims description 6
238000000576 coating method Methods 0.000 description 38
239000011248 coating agent Substances 0.000 description 36
239000007788 liquid Substances 0.000 description 32
239000010408 film Substances 0.000 description 31
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 25
239000011247 coating layer Substances 0.000 description 23
229920005989 resin Polymers 0.000 description 23
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239000000975 dye Substances 0.000 description 19
239000006185 dispersion Substances 0.000 description 16
FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 15
238000000034 method Methods 0.000 description 15
239000000126 substance Substances 0.000 description 14
239000007864 aqueous solution Substances 0.000 description 13
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OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 9
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 6
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ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 6
239000011230 binding agent Substances 0.000 description 6
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KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 6
239000002609 medium Substances 0.000 description 6
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230000015572 biosynthetic process Effects 0.000 description 5
239000003431 cross linking reagent Substances 0.000 description 5
230000007423 decrease Effects 0.000 description 5
238000011161 development Methods 0.000 description 5
125000000524 functional group Chemical group 0.000 description 5
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
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KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
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229920002472 Starch Polymers 0.000 description 4
125000005336 allyloxy group Chemical group 0.000 description 4
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 4
230000004888 barrier function Effects 0.000 description 4
230000000903 blocking effect Effects 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 4
239000000314 lubricant Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000011259 mixed solution Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
230000035945 sensitivity Effects 0.000 description 4
CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
239000008399 tap water Substances 0.000 description 4
235000020679 tap water Nutrition 0.000 description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 3
229920000298 Cellophane Polymers 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
235000010724 Wisteria floribunda Nutrition 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
229910001870 ammonium persulfate Inorganic materials 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
230000006378 damage Effects 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
238000009472 formulation Methods 0.000 description 3
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229920003023 plastic Polymers 0.000 description 3
239000004033 plastic Substances 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
239000004800 polyvinyl chloride Substances 0.000 description 3
229920000915 polyvinyl chloride Polymers 0.000 description 3
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
229910000077 silane Inorganic materials 0.000 description 3
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229920001909 styrene-acrylic polymer Polymers 0.000 description 3
238000012360 testing method Methods 0.000 description 3
239000001993 wax Substances 0.000 description 3
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 3
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
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 2
XAAILNNJDMIMON-UHFFFAOYSA-N 2'-anilino-6'-(dibutylamino)-3'-methylspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound C=1C(N(CCCC)CCCC)=CC=C(C2(C3=CC=CC=C3C(=O)O2)C2=C3)C=1OC2=CC(C)=C3NC1=CC=CC=C1 XAAILNNJDMIMON-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
OPQSLUUXOWKRPQ-UHFFFAOYSA-N 4-[4-[4-[4-(4-propan-2-yloxyphenyl)sulfonylphenoxy]butoxy]phenyl]sulfonylphenol Chemical compound C1=CC(OC(C)C)=CC=C1S(=O)(=O)C(C=C1)=CC=C1OCCCCOC1=CC=C(S(=O)(=O)C=2C=CC(O)=CC=2)C=C1 OPQSLUUXOWKRPQ-UHFFFAOYSA-N 0.000 description 2
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
241000283070 Equus zebra Species 0.000 description 2
239000001856 Ethyl cellulose Substances 0.000 description 2
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
239000002033 PVDF binder Substances 0.000 description 2
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XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
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238000009833 condensation Methods 0.000 description 2
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235000014113 dietary fatty acids Nutrition 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
238000010828 elution Methods 0.000 description 2
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235000019325 ethyl cellulose Nutrition 0.000 description 2
239000005038 ethylene vinyl acetate Substances 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
229940015043 glyoxal Drugs 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229920006284 nylon film Polymers 0.000 description 2
UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
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239000005020 polyethylene terephthalate Substances 0.000 description 2
239000005033 polyvinylidene chloride Substances 0.000 description 2
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OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 2
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YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
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150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
BIQGQLXQLYTHRA-UHFFFAOYSA-N (2-phenylnaphthalen-1-yl) hydrogen carbonate Chemical compound C1=CC2=CC=CC=C2C(OC(=O)O)=C1C1=CC=CC=C1 BIQGQLXQLYTHRA-UHFFFAOYSA-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
JZLWSRCQCPAUDP-UHFFFAOYSA-N 1,3,5-triazine-2,4,6-triamine;urea Chemical compound NC(N)=O.NC1=NC(N)=NC(N)=N1 JZLWSRCQCPAUDP-UHFFFAOYSA-N 0.000 description 1
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
LJSLYKNKVQMIJY-UHFFFAOYSA-N 1,4-diethoxynaphthalene Chemical compound C1=CC=C2C(OCC)=CC=C(OCC)C2=C1 LJSLYKNKVQMIJY-UHFFFAOYSA-N 0.000 description 1
UGRMITBWUVWUEB-UHFFFAOYSA-N 1-$l^{1}-oxidanyl-3-methylbenzene Chemical group CC1=CC=CC([O])=C1 UGRMITBWUVWUEB-UHFFFAOYSA-N 0.000 description 1
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-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
NNORAMKREOSIBW-UHFFFAOYSA-N 1-methyl-3-[(4-phenylphenyl)methoxy]benzene Chemical group CC1=CC=CC(OCC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 NNORAMKREOSIBW-UHFFFAOYSA-N 0.000 description 1
HUOKHAMXPNSWBJ-UHFFFAOYSA-N 2'-chloro-6'-(diethylamino)-3'-methylspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(Cl)=C(C)C=C1OC1=CC(N(CC)CC)=CC=C21 HUOKHAMXPNSWBJ-UHFFFAOYSA-N 0.000 description 1
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
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