JP5967461B1 - UV curable adhesive composition and adhesive sheet - Google Patents
UV curable adhesive composition and adhesive sheet Download PDFInfo
- Publication number
- JP5967461B1 JP5967461B1 JP2016519896A JP2016519896A JP5967461B1 JP 5967461 B1 JP5967461 B1 JP 5967461B1 JP 2016519896 A JP2016519896 A JP 2016519896A JP 2016519896 A JP2016519896 A JP 2016519896A JP 5967461 B1 JP5967461 B1 JP 5967461B1
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- JP
- Japan
- Prior art keywords
- sensitive adhesive
- adhesive composition
- ultraviolet curable
- mass
- meth
- 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.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 36
- 230000001070 adhesive effect Effects 0.000 title description 21
- 239000000853 adhesive Substances 0.000 title description 20
- -1 acrylic compound Chemical class 0.000 claims abstract description 74
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims abstract description 50
- 150000003077 polyols Chemical class 0.000 claims abstract description 47
- 229920005862 polyol Polymers 0.000 claims abstract description 43
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims abstract description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 14
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 14
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 6
- 239000000047 product Substances 0.000 claims abstract description 6
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 9
- 239000004417 polycarbonate Substances 0.000 claims description 8
- 239000003999 initiator Substances 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- 229920000515 polycarbonate Polymers 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 claims description 5
- 235000011187 glycerol Nutrition 0.000 claims description 3
- 230000002087 whitening effect Effects 0.000 abstract description 22
- 239000011521 glass Substances 0.000 abstract description 11
- 229910052751 metal Inorganic materials 0.000 abstract description 7
- 239000002184 metal Substances 0.000 abstract description 7
- 238000004132 cross linking Methods 0.000 abstract description 2
- 239000003505 polymerization initiator Substances 0.000 abstract description 2
- 239000004793 Polystyrene Substances 0.000 description 16
- 229920002223 polystyrene Polymers 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000006087 Silane Coupling Agent Substances 0.000 description 10
- 239000005058 Isophorone diisocyanate Substances 0.000 description 8
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 8
- 229920000139 polyethylene terephthalate Polymers 0.000 description 8
- 239000005020 polyethylene terephthalate Substances 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 7
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 229920001451 polypropylene glycol Polymers 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 5
- NXMOWTFIUDDXIT-UHFFFAOYSA-L [7,7-dimethyloctanoyloxy(dioctyl)stannyl] 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCC(C)(C)C NXMOWTFIUDDXIT-UHFFFAOYSA-L 0.000 description 5
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 239000004611 light stabiliser Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- 238000004383 yellowing Methods 0.000 description 5
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000005520 cutting process Methods 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- SKHBJDDIGYYYMJ-UHFFFAOYSA-N 2,6-ditert-butyl-6-methylcyclohexa-1,3-dien-1-ol Chemical compound CC(C)(C)C1=C(O)C(C)(C(C)(C)C)CC=C1 SKHBJDDIGYYYMJ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical class CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- UNVGBIALRHLALK-UHFFFAOYSA-N 1,5-Hexanediol Chemical compound CC(O)CCCCO UNVGBIALRHLALK-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- 239000004970 Chain extender Substances 0.000 description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- OMRDSWJXRLDPBB-UHFFFAOYSA-N N=C=O.N=C=O.C1CCCCC1 Chemical compound N=C=O.N=C=O.C1CCCCC1 OMRDSWJXRLDPBB-UHFFFAOYSA-N 0.000 description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000004734 Polyphenylene sulfide Substances 0.000 description 2
- 208000034189 Sclerosis Diseases 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- OSIVCXJNIBEGCL-UHFFFAOYSA-N bis(2,2,6,6-tetramethyl-1-octoxypiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(OCCCCCCCC)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(OCCCCCCCC)C(C)(C)C1 OSIVCXJNIBEGCL-UHFFFAOYSA-N 0.000 description 2
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 2
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
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- 230000001678 irradiating effect Effects 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
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- 230000003287 optical effect Effects 0.000 description 2
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- 229910052698 phosphorus Inorganic materials 0.000 description 2
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- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
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- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 229920001955 polyphenylene ether Polymers 0.000 description 2
- 229920000069 polyphenylene sulfide Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 150000003464 sulfur compounds Chemical class 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical class C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
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- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
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- ZAHBNGOLTBLVHO-UHFFFAOYSA-N 1,1-bis(2,6-dibutyl-4-methylphenyl)-2,2-bis(hydroxymethyl)propane-1,3-diol dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.C(CCC)C1=C(C(=CC(=C1)C)CCCC)C(O)(C(CO)(CO)CO)C1=C(C=C(C=C1CCCC)C)CCCC ZAHBNGOLTBLVHO-UHFFFAOYSA-N 0.000 description 1
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- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- QFTQDLVQRRBJHC-UHFFFAOYSA-N 1,3,7,9-tetrabutyl-11-fluoro-5-methyl-5H-benzo[d][1,3,2]benzodioxaphosphocine Chemical compound CCCCc1cc(CCCC)c2OP(F)Oc3c(CCCC)cc(CCCC)cc3C(C)c2c1 QFTQDLVQRRBJHC-UHFFFAOYSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
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- SUGGJLOBTAREMB-UHFFFAOYSA-N cyclooctane-1,1-diol Chemical compound OC1(O)CCCCCCC1 SUGGJLOBTAREMB-UHFFFAOYSA-N 0.000 description 1
- NUUPJBRGQCEZSI-UHFFFAOYSA-N cyclopentane-1,3-diol Chemical compound OC1CCC(O)C1 NUUPJBRGQCEZSI-UHFFFAOYSA-N 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- NMAKPIATXQEXBT-UHFFFAOYSA-N didecyl phenyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OC1=CC=CC=C1 NMAKPIATXQEXBT-UHFFFAOYSA-N 0.000 description 1
- ASGKDLGXPOIMTM-UHFFFAOYSA-N diethoxy-methyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](C)(OCC)OCC)CCC2OC21 ASGKDLGXPOIMTM-UHFFFAOYSA-N 0.000 description 1
- UYZLMBFZCOONBJ-UHFFFAOYSA-N diethoxy-methyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]silane Chemical compound C1C(C(C)C[Si](C)(OCC)OCC)CCC2OC21 UYZLMBFZCOONBJ-UHFFFAOYSA-N 0.000 description 1
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 description 1
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 1
- ZCGNNESZWJPBLW-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite 2-[2-(2-hydroxyphenyl)propan-2-yl]-3,4,5,6-tetra(tridecyl)phenol Chemical compound OP(O)OP(O)O.CCCCCCCCCCCCCC1=C(CCCCCCCCCCCCC)C(CCCCCCCCCCCCC)=C(O)C(C(C)(C)C=2C(=CC=CC=2)O)=C1CCCCCCCCCCCCC ZCGNNESZWJPBLW-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-UHFFFAOYSA-N 0.000 description 1
- JFHGLVIOIANSIN-UHFFFAOYSA-N dimethyl butanedioate;1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound COC(=O)CCC(=O)OC.CC1(C)CC(O)CC(C)(C)N1CCO JFHGLVIOIANSIN-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- 229940035422 diphenylamine Drugs 0.000 description 1
- KGJZNUJOFVVWCW-UHFFFAOYSA-N diphenylmethanone;2-(2-methylpropoxy)-1,2-diphenylethanone Chemical class C=1C=CC=CC=1C(=O)C1=CC=CC=C1.C=1C=CC=CC=1C(OCC(C)C)C(=O)C1=CC=CC=C1 KGJZNUJOFVVWCW-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- RRZCFXQTVDJDGF-UHFFFAOYSA-N dodecyl 3-(3-octadecoxy-3-oxopropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC RRZCFXQTVDJDGF-UHFFFAOYSA-N 0.000 description 1
- LWXXBOJIZPSHNS-UHFFFAOYSA-N dodecyl-sulfanyl-sulfanylidene-lambda4-sulfane Chemical compound CCCCCCCCCCCCS(=S)S LWXXBOJIZPSHNS-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- ZUNGGJHBMLMRFJ-UHFFFAOYSA-O ethoxy-hydroxy-oxophosphanium Chemical compound CCO[P+](O)=O ZUNGGJHBMLMRFJ-UHFFFAOYSA-O 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- HTSRFYSEWIPFNI-UHFFFAOYSA-N ethyl-dimethoxy-methylsilane Chemical compound CC[Si](C)(OC)OC HTSRFYSEWIPFNI-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- VSQYNPJPULBZKU-UHFFFAOYSA-N mercury xenon Chemical compound [Xe].[Hg] VSQYNPJPULBZKU-UHFFFAOYSA-N 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical group NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- AXRSHKZFNKUGQB-UHFFFAOYSA-N octyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCC)OC1=CC=CC=C1 AXRSHKZFNKUGQB-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 238000001782 photodegradation Methods 0.000 description 1
- 239000012994 photoredox catalyst Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000005028 tinplate Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- MZHULIWXRDLGRR-UHFFFAOYSA-N tridecyl 3-(3-oxo-3-tridecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCC MZHULIWXRDLGRR-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- SQAZDQFHAOTWGX-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]silane Chemical compound C1C(C(C)C[Si](OCC)(OCC)OCC)CCC2OC21 SQAZDQFHAOTWGX-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- LQZHZFUSFHLGHE-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]silane Chemical compound C1C(C(C)C[Si](OC)(OC)OC)CCC2OC21 LQZHZFUSFHLGHE-UHFFFAOYSA-N 0.000 description 1
- QQNZPPCHCWSYHF-UHFFFAOYSA-N tris(2,4-dibutyl-5-methylphenyl) phosphite Chemical compound C1=C(C)C(CCCC)=CC(CCCC)=C1OP(OC=1C(=CC(CCCC)=C(C)C=1)CCCC)OC1=CC(C)=C(CCCC)C=C1CCCC QQNZPPCHCWSYHF-UHFFFAOYSA-N 0.000 description 1
- CFAVHELRAWFONI-UHFFFAOYSA-N tris(2,4-dibutylphenyl) phosphite Chemical compound CCCCC1=CC(CCCC)=CC=C1OP(OC=1C(=CC(CCCC)=CC=1)CCCC)OC1=CC=C(CCCC)C=C1CCCC CFAVHELRAWFONI-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- ISIZMFAUIWBRRW-UHFFFAOYSA-N tris[2-tert-butyl-4-(3-butyl-4-hydroxy-5-methylphenyl)sulfanyl-5-methylphenyl] phosphite Chemical compound P(OC1=C(C=C(C(=C1)C)SC1=CC(=C(C(=C1)C)O)CCCC)C(C)(C)C)(OC1=C(C=C(C(=C1)C)SC1=CC(=C(C(=C1)C)O)CCCC)C(C)(C)C)OC1=C(C=C(C(=C1)C)SC1=CC(=C(C(=C1)C)O)CCCC)C(C)(C)C ISIZMFAUIWBRRW-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyurethanes Or Polyureas (AREA)
- Adhesive Tapes (AREA)
Abstract
本発明が解決しようとする課題は、金属板やガラス板等の高極性な被着体への密着性及び耐湿熱白化性に優れる紫外線硬化型粘着剤組成物を提供することである。本発明は、ポリオール(a1)とポリイソシアネート(a2)と水酸基を2個以上有する(メタ)アクリル化合物(a3)との反応物であり、末端に水酸基を有するウレタン樹脂(A)、及び、光重合開始剤(B)を含有することを特徴とする紫外線硬化型粘着剤組成物、及び前記紫外線硬化型粘着剤組成物の硬化物層を有することを特徴とする粘着シートを提供するものである。本発明の紫外線硬化型粘着剤組成物は、熱架橋及び紫外線硬化を併用し得るものであり、金属板やガラス板等の高極性な被着体への密着性及び耐湿熱白化性に優れるものである。The problem to be solved by the present invention is to provide an ultraviolet curable pressure-sensitive adhesive composition that is excellent in adhesion to a highly polar adherend such as a metal plate or a glass plate and in resistance to moist heat whitening. The present invention is a reaction product of a polyol (a1), a polyisocyanate (a2), and a (meth) acrylic compound (a3) having two or more hydroxyl groups, a urethane resin (A) having a hydroxyl group at the terminal, and light. An ultraviolet curable pressure-sensitive adhesive composition comprising a polymerization initiator (B), and a pressure-sensitive adhesive sheet comprising a cured product layer of the ultraviolet curable pressure-sensitive adhesive composition are provided. . The ultraviolet curable pressure-sensitive adhesive composition of the present invention can be used in combination with thermal crosslinking and ultraviolet curing, and has excellent adhesion to highly polar adherends such as metal plates and glass plates, and resistance to moisture and heat whitening. It is.
Description
本発明は、高極性な被着体への密着性及び耐湿熱白化性に優れる紫外線硬化型粘着剤組成物に関する。 The present invention relates to an ultraviolet curable pressure-sensitive adhesive composition that is excellent in adhesion to a highly polar adherend and moisture and heat whitening resistance.
粘着剤製品は、作業性の良さから、主に工業分野での用途拡大を続けており、今後も伸長が期待されている。特に、紫外線硬化型粘着剤は、熱硬化型粘着剤では必須工程であるエージング時間が不要であることから、高生産性が期待でき、需要拡大が確実視されている。 Adhesive products continue to expand applications mainly in the industrial field due to their good workability, and are expected to grow in the future. In particular, ultraviolet curable adhesives do not require aging time, which is an essential process for thermosetting adhesives, and thus high productivity can be expected, and demand is expected to increase.
前記紫外線硬化型粘着剤としては、例えば、末端に(メタ)アクリロイル基を有するウレタンアクリレート、アクリル単量体及び光重合開始剤を含有する無溶剤型粘着剤組成物を用いて得られた粘着剤が知られている(例えば、特許文献1を参照。)。 Examples of the ultraviolet curable pressure-sensitive adhesive include a pressure-sensitive adhesive obtained using a solventless pressure-sensitive adhesive composition containing a urethane acrylate having a (meth) acryloyl group at the terminal, an acrylic monomer, and a photopolymerization initiator. Is known (see, for example, Patent Document 1).
しかしながら、前記粘着剤では金属板やガラス板等の高極性の被着体への密着性が不良であることや、耐湿熱白化性が不良であるとの問題点があった。 However, the pressure-sensitive adhesive has a problem that it has poor adhesion to a highly polar adherend such as a metal plate or glass plate, and has poor heat and heat whitening resistance.
本発明が解決しようとする課題は、金属板やガラス板等の高極性な被着体への密着性及び耐湿熱白化性に優れる紫外線硬化型粘着剤組成物を提供することである。 The problem to be solved by the present invention is to provide an ultraviolet curable pressure-sensitive adhesive composition that is excellent in adhesion to a highly polar adherend such as a metal plate or a glass plate and in resistance to moist heat whitening.
本発明は、ポリオール(a1)とポリイソシアネート(a2)と水酸基を2個以上有する(メタ)アクリル化合物(a3)との反応物であり、末端に水酸基を有するウレタン樹脂(A)、及び、光重合開始剤(B)を含有することを特徴とする紫外線硬化型粘着剤組成物、及び前記紫外線硬化型粘着剤組成物の硬化物層を有することを特徴とする粘着シートを提供するものである。 The present invention is a reaction product of a polyol (a1), a polyisocyanate (a2), and a (meth) acrylic compound (a3) having two or more hydroxyl groups, a urethane resin (A) having a hydroxyl group at the terminal, and light. An ultraviolet curable pressure-sensitive adhesive composition comprising a polymerization initiator (B), and a pressure-sensitive adhesive sheet comprising a cured product layer of the ultraviolet curable pressure-sensitive adhesive composition are provided. .
本発明の紫外線硬化型粘着剤組成物は、金属板やガラス板等の高極性な被着体への密着性及び耐湿熱白化性に優れるものである。本発明の紫外線硬化型粘着剤組成物は、医療用、文具用、光学部材用等の様々な分野の粘着シートとして好適に使用することができる。 The ultraviolet curable pressure-sensitive adhesive composition of the present invention is excellent in adhesion to a highly polar adherend such as a metal plate and a glass plate, and resistance to moist heat whitening. The ultraviolet curable pressure-sensitive adhesive composition of the present invention can be suitably used as a pressure-sensitive adhesive sheet in various fields such as medical use, stationery use, and optical member use.
本発明の紫外線硬化型粘着剤組成物は、ポリオール(a1)とポリイソシアネート(a2)と水酸基を2個以上有する(メタ)アクリル化合物(a3)との反応物であり、末端に水酸基を有するウレタン樹脂(A)、及び、光重合開始剤(B)を含有するものである。 The ultraviolet curable pressure-sensitive adhesive composition of the present invention is a reaction product of a polyol (a1), a polyisocyanate (a2), and a (meth) acrylic compound (a3) having two or more hydroxyl groups, and a urethane having a hydroxyl group at the terminal. Resin (A) and a photoinitiator (B) are contained.
前記ウレタン樹脂(A)は、末端に高極性な水酸基を有するため、高極性な被着体への優れた密着性を発現することができる。特に、分子末端はフレキシビリティが高く、密着性への寄与が大きいと考えられる。また、前記ウレタン樹脂(A)は、その製造中に前記(a3)が有する2個以上の水酸基がポリイソシアネート(a2)と反応し分子鎖中に取り込まれるため、ウレタン樹脂(A)の分子内に(メタ)アクリロイル基が存在することとなる。よって、この(メタ)アクリロイル基は紫外線照時にウレタン樹脂(A)間で架橋するため、架橋密度の向上により優れた耐湿熱白化性を発現することができる。 Since the urethane resin (A) has a highly polar hydroxyl group at the terminal, it can exhibit excellent adhesion to a highly polar adherend. In particular, the molecular terminals are considered to have high flexibility and contribute greatly to adhesion. In addition, since the urethane resin (A) has two or more hydroxyl groups in the (a3) react with the polyisocyanate (a2) and is taken into the molecular chain during its production, the urethane resin (A) has an intramolecular structure. (Meth) acryloyl group will be present. Therefore, since this (meth) acryloyl group crosslinks between the urethane resins (A) at the time of ultraviolet irradiation, it is possible to express excellent moisture and heat whitening resistance by improving the crosslink density.
前記ポリオール(a1)としては、例えば、ポリエーテルポリオール、ポリカーボネートポリオール、ポリエステルポリオール、ポリブタジエンポリオール、水添ポリブタジエンポリオール、ポリアクリルポリオール、ダイマージオール、ポリイソプレンポリオール等を用いることができる。これらのポリオールは単独で用いても2種以上を併用してもよい。これらの中でも、その骨格により非常に優れた耐湿熱白化性が得られる点から、ポリエーテルポリオール及び/又はポリカーボネートポリオールを含有することが好ましい。 Examples of the polyol (a1) include polyether polyol, polycarbonate polyol, polyester polyol, polybutadiene polyol, hydrogenated polybutadiene polyol, polyacryl polyol, dimer diol, polyisoprene polyol, and the like. These polyols may be used alone or in combination of two or more. Among these, it is preferable to contain a polyether polyol and / or a polycarbonate polyol from the viewpoint that the heat and whitening resistance which is very excellent by the skeleton is obtained.
前記ポリエーテルポリオールとしては、例えば、ポリオキシエチレンポリオール、ポリオキシプロピレンポリオール、ポリオキシテトラメチレンポリオール、ポリオキシエチレンポリオキシプロピレンポリオール、ポリオキシエチレンポリオキシテトラメチレンポリオール、ポリオキシプロピレンポリオキシテトラメチレンポリオール等を用いることができる。これらのポリエーテルポリオールは単独で用いても2種以上を併用してもよい。これらの中でも、耐湿熱白化性、及び、柔軟性をより一層向上できる点から、ポリオキシエチレンポリオール、ポリオキシプロピレンポリオール及びポリオキシテトラメチレンポリオールからなる群より選ばれる1種以上のポリエーテルポリオールを用いることが好ましい。 Examples of the polyether polyol include polyoxyethylene polyol, polyoxypropylene polyol, polyoxytetramethylene polyol, polyoxyethylene polyoxypropylene polyol, polyoxyethylene polyoxytetramethylene polyol, polyoxypropylene polyoxytetramethylene polyol. Etc. can be used. These polyether polyols may be used alone or in combination of two or more. Among these, at least one polyether polyol selected from the group consisting of polyoxyethylene polyol, polyoxypropylene polyol, and polyoxytetramethylene polyol is used because it can further improve the resistance to moist heat and whitening and flexibility. It is preferable to use it.
前記ポリカーボネートポリオールとしては、例えば、炭酸エステル及び/又はホスゲンと、2個以上の水酸基を有する化合物とを反応させて得られるものを用いることができる。 As said polycarbonate polyol, what is obtained by making carbonate ester and / or phosgene react with the compound which has a 2 or more hydroxyl group can be used, for example.
前記炭酸エステルとしては、例えば、メチルカーボネート、ジメチルカーボネート、エチルカーボネート、ジエチルカーボネート、シクロカーボネート、ジフェニルカーボネート等を用いることができる。これらの炭酸エステルは単独で用いても2種以上を併用してもよい。 As the carbonate ester, for example, methyl carbonate, dimethyl carbonate, ethyl carbonate, diethyl carbonate, cyclocarbonate, diphenyl carbonate and the like can be used. These carbonates may be used alone or in combination of two or more.
また、前記2個以上の水酸基を有する化合物としては、例えば、エチレングリコール、ジエチレングリコール、トリエチレングリコール、テトラエチレングリコール、1,2−プロパンジオール、1,3−プロパンジオール、ジプロピレングリコール、トリプロピレングリコール、1,2−ブタンジオール、1,3−ブタンジオール、1,4−ブタンジオール、2,3−ブタンジオール、1,5−ペンタンジオール、1,5−ヘキサンジオール、1,6−ヘキサンジオール、2,5−ヘキサンジオール、1,7−ヘプタンジオール、1,8−オクタンジオール、1,9−ノナンジオール、1,10−デカンジオール、1,11−ウンデカンジオール、1,12−ドデカンジオール、2−メチル−1,3−プロパンジオール、ネオペンチルグリコール、2−ブチル−2−エチル−1,3−プロパンジオール、3−メチル−1,5−ペンタンジオール、2−エチル−1,3−ヘキサンジオール、2−メチル−1,8−オクタンジオール等の脂肪族ポリオール;1,2−シクロブタンジオール、1,3−シクロペンタンジオール、1,4−シクロヘキサンジメタノール、シクロヘプタンジオール、シクロオクタンジオール、ヒドロキシプロピルシクロヘキサノール等の脂環式ポリオール;ビスフェノールA、ビスフェノールF、4,4’−ビフェノール等の芳香族ポリオールなどを用いることができる。これらの化合物は単独で用いても2種以上を併用してもよい。これらの中でも、カッティング性(裁断時に糊残りがない)をより一層向上できる点から、脂肪族ポリオール及び/又は脂環式ポリオールを用いることが好ましく、1,4−ブタンジオール、1,5−ペンタンジオール、1,6−ヘキサンジオール、1,4−シクロヘキサンジメタノールからなる群より選ばれる1種以上の化合物を用いることがより好ましい。 Examples of the compound having two or more hydroxyl groups include ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, 1,2-propanediol, 1,3-propanediol, dipropylene glycol, and tripropylene glycol. 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 1,5-pentanediol, 1,5-hexanediol, 1,6-hexanediol, 2,5-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,11-undecanediol, 1,12-dodecanediol, 2 -Methyl-1,3-propanediol, neopentylglyce 2-butyl-2-ethyl-1,3-propanediol, 3-methyl-1,5-pentanediol, 2-ethyl-1,3-hexanediol, 2-methyl-1,8-octanediol Aliphatic polyols such as 1,2-cyclobutanediol, 1,3-cyclopentanediol, 1,4-cyclohexanedimethanol, cycloheptanediol, cyclooctanediol, hydroxypropylcyclohexanol, etc .; bisphenol A An aromatic polyol such as bisphenol F or 4,4′-biphenol can be used. These compounds may be used alone or in combination of two or more. Among these, it is preferable to use an aliphatic polyol and / or an alicyclic polyol from the viewpoint that the cutting property (no adhesive residue at the time of cutting) can be further improved, and 1,4-butanediol, 1,5-pentane It is more preferable to use one or more compounds selected from the group consisting of diol, 1,6-hexanediol, and 1,4-cyclohexanedimethanol.
前記ポリオール(a1)の数平均分子量としては、耐湿熱白化性、柔軟性及び、機械的強度の点から、500〜7,000の範囲であることが好ましく、700〜4,000の範囲がより好ましく、800〜3,000の範囲が更に好ましい。なお、前記ポリオール(a1)の数平均分子量は、ゲル・パーミエーション・クロマトグラフィー(GPC)法により、下記条件で測定した値を示す。 The number average molecular weight of the polyol (a1) is preferably in the range of 500 to 7,000, more preferably in the range of 700 to 4,000, from the viewpoints of heat and heat whitening resistance, flexibility, and mechanical strength. The range of 800 to 3,000 is more preferable. In addition, the number average molecular weight of the said polyol (a1) shows the value measured on condition of the following by gel permeation chromatography (GPC) method.
測定装置:高速GPC装置(東ソー株式会社製「HLC−8220GPC」)
カラム:東ソー株式会社製の下記のカラムを直列に接続して使用した。
「TSKgel G5000」(7.8mmI.D.×30cm)×1本
「TSKgel G4000」(7.8mmI.D.×30cm)×1本
「TSKgel G3000」(7.8mmI.D.×30cm)×1本
「TSKgel G2000」(7.8mmI.D.×30cm)×1本
検出器:RI(示差屈折計)
カラム温度:40℃
溶離液:テトラヒドロフラン(THF)
流速:1.0mL/分
注入量:100μL(試料濃度0.4質量%のテトラヒドロフラン溶液)
標準試料:下記の標準ポリスチレンを用いて検量線を作成した。Measuring device: High-speed GPC device (“HLC-8220GPC” manufactured by Tosoh Corporation)
Column: The following columns manufactured by Tosoh Corporation were connected in series.
"TSKgel G5000" (7.8 mm ID x 30 cm) x 1 "TSKgel G4000" (7.8 mm ID x 30 cm) x 1 "TSKgel G3000" (7.8 mm ID x 30 cm) x 1 “TSKgel G2000” (7.8 mm ID × 30 cm) × 1 detector: RI (differential refractometer)
Column temperature: 40 ° C
Eluent: Tetrahydrofuran (THF)
Flow rate: 1.0 mL / min Injection amount: 100 μL (tetrahydrofuran solution with a sample concentration of 0.4 mass%)
Standard sample: A calibration curve was prepared using the following standard polystyrene.
(標準ポリスチレン)
東ソー株式会社製「TSKgel 標準ポリスチレン A−500」
東ソー株式会社製「TSKgel 標準ポリスチレン A−1000」
東ソー株式会社製「TSKgel 標準ポリスチレン A−2500」
東ソー株式会社製「TSKgel 標準ポリスチレン A−5000」
東ソー株式会社製「TSKgel 標準ポリスチレン F−1」
東ソー株式会社製「TSKgel 標準ポリスチレン F−2」
東ソー株式会社製「TSKgel 標準ポリスチレン F−4」
東ソー株式会社製「TSKgel 標準ポリスチレン F−10」
東ソー株式会社製「TSKgel 標準ポリスチレン F−20」
東ソー株式会社製「TSKgel 標準ポリスチレン F−40」
東ソー株式会社製「TSKgel 標準ポリスチレン F−80」
東ソー株式会社製「TSKgel 標準ポリスチレン F−128」
東ソー株式会社製「TSKgel 標準ポリスチレン F−288」
東ソー株式会社製「TSKgel 標準ポリスチレン F−550」(Standard polystyrene)
"TSKgel standard polystyrene A-500" manufactured by Tosoh Corporation
"TSKgel standard polystyrene A-1000" manufactured by Tosoh Corporation
"TSKgel standard polystyrene A-2500" manufactured by Tosoh Corporation
"TSKgel standard polystyrene A-5000" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-1" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-2" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-4" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-10" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-20" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-40" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-80" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-128" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-288" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-550" manufactured by Tosoh Corporation
前記ポリオール(a1)には、必要に応じて水酸基を有する数平均分子量50〜400の範囲の鎖伸長剤を併用してもよい。 The polyol (a1) may be used in combination with a chain extender having a hydroxyl group and having a number average molecular weight in the range of 50 to 400, if necessary.
前記水酸基を有する鎖伸長剤としては、前記2個以上の水酸基を有する化合物と同様のものを用いることができる。中でも、適度な鎖長のハードセグメントをウレタン樹脂(A)に導入でき、非常に優れた耐湿熱白化性が得られる点から、1,4−ブタンジオール、1,5−ペンタンジオール、1,6−ヘキサンジオール、及び1,4−シクロヘキサンジメタノールからなる群より選ばれる1種以上の化合物を用いることがより好ましい。 As the chain extender having a hydroxyl group, those similar to the compound having two or more hydroxyl groups can be used. Among these, 1,4-butanediol, 1,5-pentanediol, 1,6 from the viewpoint that a hard segment having an appropriate chain length can be introduced into the urethane resin (A), and excellent moisture and heat whitening resistance can be obtained. -It is more preferable to use one or more compounds selected from the group consisting of hexanediol and 1,4-cyclohexanedimethanol.
前記ポリイソシアネート(a2)としては、例えば、キシリレンジイソシアネート、フェニレンジイソシアネート、トリレンジイソシアネート、ジフェニルメタンジイソシアネート、ナフタレンジイソシアネート等の芳香族ポリイソシアネート;ヘキサメチレンジイソシアネート、リジンジイソシアネート、シクロヘキサンジイソシアネート、イソホロンジイソシアネート、4,4’−ジシクロヘキシルメタンジイソシアネート、ジイソシアナートメチルシクロヘキサン、テトラメチルキシリレンジイソシアネート等の脂肪族又は脂環式ポリイソシアネートなどを用いることができる。これらのポリイソシアネートは単独で用いても2種以上を併用してもよい。これらの中でも、機械的強度、粘着物性及び透明性をより一層向上できる点から、脂環式ポリイソシアネートを用いることが好ましく、4,4’−ジシクロヘキシルメタンジイソシアネート、イソホロンジイソシアネート、シクロヘキサンジイソシアネート及びジイソシアナートメチルシクロヘキサンからなる群より選ばれる1種以上のポリイソシアネートを用いることがより好ましい。 Examples of the polyisocyanate (a2) include aromatic polyisocyanates such as xylylene diisocyanate, phenylene diisocyanate, tolylene diisocyanate, diphenylmethane diisocyanate, and naphthalene diisocyanate; hexamethylene diisocyanate, lysine diisocyanate, cyclohexane diisocyanate, isophorone diisocyanate, 4,4 Aliphatic or alicyclic polyisocyanates such as' -dicyclohexylmethane diisocyanate, diisocyanate methylcyclohexane, and tetramethylxylylene diisocyanate can be used. These polyisocyanates may be used alone or in combination of two or more. Among these, it is preferable to use alicyclic polyisocyanate from the point that mechanical strength, adhesive physical properties and transparency can be further improved, and 4,4′-dicyclohexylmethane diisocyanate, isophorone diisocyanate, cyclohexane diisocyanate and diisocyanate. It is more preferable to use one or more polyisocyanates selected from the group consisting of methylcyclohexane.
前記水酸基を2個以上有する(メタ)アクリル化合物(a3)は、ウレタン樹脂(A)の分子内に(メタ)アクリロイル基を導入する目的で用いるものである。ウレタン樹脂に(メタ)アクリロイル基を導入する方法としては、水酸基又はイソシアネートを1個有する(メタ)アクリル化合物を用いる方法があるが、この場合にはウレタン樹脂(A)の末端にしか(メタ)アクリロイル基を導入することができないため、架橋密度をそれ以上増加させることができず、所望の耐湿熱白化性が得られない。一方、本発明のように前記(メタ)アクリル化合物(a3)を用いた場合には、ウレタン樹脂(A)間の架橋密度を増加させることができるため、水分の侵入を防ぎ優れた耐湿熱白化性が得られる。 The (meth) acrylic compound (a3) having two or more hydroxyl groups is used for the purpose of introducing a (meth) acryloyl group into the molecule of the urethane resin (A). As a method of introducing a (meth) acryloyl group into a urethane resin, there is a method of using a (meth) acrylic compound having one hydroxyl group or one isocyanate, and in this case, only the end of the urethane resin (A) is (meth). Since an acryloyl group cannot be introduced, the crosslink density cannot be increased any further, and the desired moisture and heat whitening resistance cannot be obtained. On the other hand, when the (meth) acrylic compound (a3) is used as in the present invention, the crosslink density between the urethane resins (A) can be increased. Sex is obtained.
前記(メタ)アクリル化合物(a3)としては、例えば、グリセリンモノ(メタ)アクリレート、3,4−ジヒドロキシブチル(メタ)アクリレート、トリメチロールプロパンモノ(メタ)アクリレート、ペンタエリスリトールジ(メタ)アクリレート、ジペンタエリスリトールテトラ(メタ)アクリレート等を用いることができる。これらの化合物は単独で用いても2種以上を併用してもよい。これらの中でも、良好な紫外線硬化性を有し、優れた耐湿熱白化性が得られる点から、水酸基を2個及び(メタ)アクリロイル基を1個有する(メタ)アクリル化合物を用いることが好ましく、グリセリンモノ(メタ)アクリレート及び/又は3,4−ジヒドロキシブチル(メタ)アクリレートを用いることがより好ましい。 Examples of the (meth) acrylic compound (a3) include glycerin mono (meth) acrylate, 3,4-dihydroxybutyl (meth) acrylate, trimethylolpropane mono (meth) acrylate, pentaerythritol di (meth) acrylate, and di Pentaerythritol tetra (meth) acrylate or the like can be used. These compounds may be used alone or in combination of two or more. Among these, it is preferable to use a (meth) acryl compound having two hydroxyl groups and one (meth) acryloyl group from the viewpoint of having good ultraviolet curability and obtaining excellent moisture and heat whitening resistance. It is more preferable to use glycerin mono (meth) acrylate and / or 3,4-dihydroxybutyl (meth) acrylate.
前記(メタ)アクリル化合物(a3)の使用量としては、紫外線硬化性、及び耐湿熱白化性の点から、前記ポリオール(a1)100質量部に対して、0.1〜30質量部の範囲であることが好ましく、0.5〜10質量部の範囲がより好ましい。 As the usage-amount of the said (meth) acrylic compound (a3), it is 0.1-30 mass parts with respect to 100 mass parts of said polyols (a1) from the point of ultraviolet sclerosis | hardenability and wet heat whitening resistance. It is preferable that the range is 0.5 to 10 parts by mass.
前記ウレタン樹脂(A)の製造方法としては、例えば、無溶剤下で、前記ポリオール(a1)と前記(メタ)アクリル化合物(a3)とを仕込み、次いで前記ポリイソシアネート(a2)を供給し、混合、反応させることによって製造する方法等を用いることができる。前記反応は、例えば20〜120℃の条件下で30分〜24時間行うことが好ましい。 As a method for producing the urethane resin (A), for example, the polyol (a1) and the (meth) acrylic compound (a3) are charged in the absence of a solvent, and then the polyisocyanate (a2) is supplied and mixed. The method of manufacturing by making it react can be used. The reaction is preferably performed, for example, at 20 to 120 ° C. for 30 minutes to 24 hours.
前記ウレタン樹脂(A)は優れた高極性な被着体への密着性を得るうえで、末端に好ましくは2個以上の水酸基を有するものである。前記ウレタン樹脂(A)を製造する際の、前記ポリオール(a1)と前記ポリイソシアネート(a2)と前記(メタ)アクリル化合物(a3)との反応は、前記ポリオール(a1)が有する水酸基及び前記(メタ)アクリル化合物(a3)が有する水酸基の合計量と、ポリイソシアネート(a2)の有するイソシアネート基とのモル比[水酸基の合計量/イソシアネート基]=1.01〜3の範囲で行うことが、ウレタン樹脂(A)の分子量と制御でき、かつ高極性な被着体への密着性をより一層向上できることから好ましく、1.1〜2の範囲であることがより好ましい。 The urethane resin (A) preferably has two or more hydroxyl groups at the end in order to obtain excellent adhesion to a highly polar adherend. The reaction of the polyol (a1), the polyisocyanate (a2), and the (meth) acrylic compound (a3) when producing the urethane resin (A) is carried out by reacting the hydroxyl group of the polyol (a1) and the ( The molar ratio of the total amount of hydroxyl groups possessed by the (meth) acrylic compound (a3) and the isocyanate group possessed by the polyisocyanate (a2) [total amount of hydroxyl groups / isocyanate group] = 1. It is preferable because the molecular weight of the urethane resin (A) can be controlled, and adhesion to a highly polar adherend can be further improved, and the range of 1.1 to 2 is more preferable.
ウレタン樹脂(A)を製造する際には、必要に応じて重合禁止剤、ウレタン化触媒等を用いてもよい。 When manufacturing a urethane resin (A), you may use a polymerization inhibitor, a urethanization catalyst, etc. as needed.
前記重合禁止剤としては、例えば、3,5−ビスターシャリーブチル−4−ヒドロキシトルエン、ハイドロキノン、メチルハイドロキノン、ハイドロキノンモノメチルエーテル(メトキノン)、パラターシャリーブチルカテコールメトキシフェノール、2,6−ジターシャリーブチルクレゾール、フェノチアジン、テトラメチルチウラムジスルフィド、ジフェニルアミン、ジニトロベンゼン等を用いることができる。これらの重合禁止剤は単独で用いても2種以上を併用してもよい。 Examples of the polymerization inhibitor include 3,5-bistertiary butyl-4-hydroxytoluene, hydroquinone, methyl hydroquinone, hydroquinone monomethyl ether (methoquinone), para tertiary butyl catechol methoxyphenol, and 2,6-ditertiary butyl cresol. Phenothiazine, tetramethylthiuram disulfide, diphenylamine, dinitrobenzene and the like can be used. These polymerization inhibitors may be used alone or in combination of two or more.
前記ウレタン化触媒としては、例えば、トリエチルアミン、トリエチレンジアミン、N−メチルモルホリン等の含窒素化合物;酢酸カリウム、ステアリン酸亜鉛、オクチル酸錫等の金属塩;ジブチルチンラウレート、ジルコニウムテトラアセチルアセトネート等の有機金属化合物などを用いることができる。これらのウレタン化触媒は単独で用いても2種以上を併用してもよい。 Examples of the urethanization catalyst include nitrogen-containing compounds such as triethylamine, triethylenediamine, and N-methylmorpholine; metal salts such as potassium acetate, zinc stearate, and tin octylate; dibutyltin laurate, zirconium tetraacetylacetonate, and the like. These organometallic compounds can be used. These urethanization catalysts may be used alone or in combination of two or more.
前記ウレタン樹脂(A)中における(メタ)アクリロイル基の含有量としては、良好な紫外線硬化による優れた耐湿熱白化性が得られ点から、0.01〜2mol/kgの範囲であることが好ましく、0.03〜0.5mol/kgの範囲であることがより好ましい。 The content of the (meth) acryloyl group in the urethane resin (A) is preferably in the range of 0.01 to 2 mol / kg from the viewpoint of obtaining excellent heat and heat whitening resistance by good ultraviolet curing. The range of 0.03 to 0.5 mol / kg is more preferable.
前記ウレタン樹脂(A)中のウレタン結合の質量割合としては、水素結合により良好なカッティング性、粘着物性及び耐湿熱白化性が得られる点から、ウレタン樹脂(A)の全量中4〜20質量%の範囲であることが好ましく、5〜15質量%の範囲であることがより好ましい。なお、前記ウレタン樹脂(A)のウレタン結合量は、前記ウレタン樹脂(A)の原料の合計質量に対する、前記原料中に占めるウレタン結合構造の質量割合を示す。 As a mass ratio of the urethane bond in the urethane resin (A), 4 to 20% by mass in the total amount of the urethane resin (A) is obtained from the point that good cutting properties, adhesive physical properties and wet heat whitening resistance can be obtained by hydrogen bonding. It is preferable that it is the range of 5-15 mass%. In addition, the urethane bond amount of the said urethane resin (A) shows the mass ratio of the urethane bond structure which occupies in the said raw material with respect to the total mass of the raw material of the said urethane resin (A).
前記ウレタン樹脂(A)の重量平均分子量としては、カッティング性、粘着物性及び高極性な被着体への密着性をより一層向上できる点から、5,000〜100,000の範囲であることが好ましく、15,000〜50,000の範囲がより好ましい。なお、前記ウレタン樹脂(A)の重量平均分子量は、前記ポリオール(a1)の数平均分子量と同様に測定して得られた値を示す。 The weight average molecular weight of the urethane resin (A) is in the range of 5,000 to 100,000 from the viewpoint of further improving cutting properties, adhesive physical properties, and adhesion to a highly polar adherend. The range of 15,000 to 50,000 is more preferable. In addition, the weight average molecular weight of the said urethane resin (A) shows the value obtained by measuring similarly to the number average molecular weight of the said polyol (a1).
前記光重合開始剤(B)は、光照射や加熱等によってラジカルを発生し、前記ウレタン樹脂(A)のラジカル重合を開始させるものである。 The photopolymerization initiator (B) generates radicals by light irradiation, heating, or the like, and starts radical polymerization of the urethane resin (A).
前記光重合開始剤(B)としては、例えば、4−フェノキシジクロロアセトフェノン、ジエトキシアセトフェノン、2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、1−(4−イソプロピルフェニル)−2−ヒドロキシ−2−メチルプロパン−1−オン、1−ヒドロキシシクロヘキシルフェニルケトン、4−(2−ヒドロキシエトキシ)−フェニル(2−ヒドロキシ−2−プロピル)ケトン、2−メチル−[4−(メチルチオ)フェニル]−2−モルフォリノ−1−プロパノン、2,2−ジメトキシ−2−フェニルアセトフェノン等のアセトフェノン化合物;ベンゾイン、ベンゾインメチルエーテル、ベンゾインイソエチルエーテル、ベンゾインイソプロピルエーテル、ベンゾインイソブチルエーテル等のベンゾイン化合物;ベンゾフェノン、ベンゾイル安息香酸、ベンゾイル安息香酸メチル、4−フェニルベンゾフェノン、ヒドロキシベンゾフェノン、4−ベンゾイル−4’−メチルジフェニルサルファイド、3,3’−ジメチル−4−メトキシベンゾフェノン等のベンゾフェノン化合物;チオキサントン、2−クロロチオキサントン、2,4−ジクロロチオキサントン、2−メチルチオキサントン、2,4−ジメチルチオキサントン、2,4−ジエチルチオキサントン、イソプロピルチオキサントン、2,4−ジイソプロピルチオキサントン等のチオキサントン化合物;4,4’−ジメチルアミノチオキサントン(別名=ミネラーズケトン)、4,4’−ジエチルアミノベンゾフェノン、α−アシロキシムエステル、ベンジル、メチルベンゾイルホルメート(「バイアキュア55」)、2−エチルアンスラキノン等のアンスラキノン化合物;2,4,6−トリメチルベンゾイルジフェニルホスフィンオキサイド、ビス(2,4,6−トリメチルベンゾイル)−フェニルホスフィンオキサイド等のアシルフォスフィンオキサイド化合物;3,3’,4,4’−テトラ(tert−ブチルオパーオキシカルボニル)ベンゾフェノン、アクリル化ベンゾフェノン等を用いることができる。これらの光重合開始剤は単独で用いても2種以上を併用してもよい。 Examples of the photopolymerization initiator (B) include 4-phenoxydichloroacetophenone, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, and 1- (4-isopropylphenyl) -2. -Hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 4- (2-hydroxyethoxy) -phenyl (2-hydroxy-2-propyl) ketone, 2-methyl- [4- (methylthio) Acetophenone compounds such as phenyl] -2-morpholino-1-propanone and 2,2-dimethoxy-2-phenylacetophenone; benzoin compounds such as benzoin, benzoin methyl ether, benzoin isoethyl ether, benzoin isopropyl ether and benzoin isobutyl ether Benzophenone compounds such as benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, 3,3′-dimethyl-4-methoxybenzophenone; thioxanthone, 2- Thioxanthone compounds such as chlorothioxanthone, 2,4-dichlorothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone; 4,4′-dimethylamino Thioxanthone (also known as Minerals ketone), 4,4′-diethylaminobenzophenone, α-acyloxime ester, benzyl, methylbenzoylformate (“ Viacure 55 "), anthraquinone compounds such as 2-ethylanthraquinone; acylphosphine oxide compounds such as 2,4,6-trimethylbenzoyldiphenylphosphine oxide and bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide 3,3 ′, 4,4′-tetra (tert-butyloperoxycarbonyl) benzophenone, acrylated benzophenone, and the like can be used. These photopolymerization initiators may be used alone or in combination of two or more.
前記光重合開始剤(B)としては、粘着物性、紫外線硬化性及び耐湿熱白化性をより一層向上できる点から、2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、1−ヒドロキシシクロヘキシルフェニルケトン、2,4,6−トリメチルベンゾイルジフェニルホスフィンオキサイド及びビス(2,4,6−トリメチルベンゾイル)−フェニルホスフィンオキサイドからなる群より選ばれる1種以上の光重合開始剤を用いることが好ましく、2,4,6−トリメチルベンゾイルジフェニルホスフィンオキサイドがより好ましい。 As the photopolymerization initiator (B), 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-hydroxy is preferable because it can further improve the adhesive properties, ultraviolet curability and wet heat whitening resistance. It is preferable to use at least one photopolymerization initiator selected from the group consisting of cyclohexyl phenyl ketone, 2,4,6-trimethylbenzoyldiphenylphosphine oxide and bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide. 2,4,6-trimethylbenzoyldiphenylphosphine oxide is more preferable.
前記光重合開始剤(B)の使用量としては、粘着物性、紫外線硬化性及び耐湿熱白化性をより一層向上できる点から、前記ウレタン樹脂(A)100質量部に対して、0.01〜20質量部の範囲であることが好ましく、0.1〜15質量部の範囲がより好ましい。 As a usage-amount of the said photoinitiator (B), it is 0.01-0.1 with respect to 100 mass parts of said urethane resins (A) from the point which can further improve adhesive physical property, ultraviolet sclerosis | hardenability, and heat-and-moisture whitening resistance. The range is preferably 20 parts by mass, and more preferably 0.1 to 15 parts by mass.
本発明の紫外線硬化型粘着剤組成物は、必要に応じてその他の添加剤を含有してもよい。 The ultraviolet curable pressure-sensitive adhesive composition of the present invention may contain other additives as necessary.
前記その他の添加剤としては、例えば、有機溶剤、シランカップリング剤、酸化防止剤、光安定剤、防錆剤、チキソ性付与剤、増感剤、重合禁止剤、レベリング剤、粘着付与剤、帯電防止剤、難燃剤等を用いることができる。これらの添加剤は単独で用いても2種以上を併用してもよい。これらの中でも、被着体への塗工性及び作業性の点から有機溶剤を含有することが好ましい。また、本発明の紫外線硬化型粘着剤組成物が耐湿熱後に高い粘着物性を要求される用途に使用される場合には、シランカップリング剤を含有することが好ましい。また、本発明の紫外線硬化型粘着剤組成物が高い耐湿熱黄変性を要求される用途に使用される場合には、酸化防止剤及び光安定剤を含有することが好ましい。 Examples of the other additives include organic solvents, silane coupling agents, antioxidants, light stabilizers, rust inhibitors, thixotropic agents, sensitizers, polymerization inhibitors, leveling agents, tackifiers, An antistatic agent, a flame retardant, etc. can be used. These additives may be used alone or in combination of two or more. Among these, it is preferable to contain the organic solvent from the point of the coating property to a to-be-adhered body, and workability | operativity. Moreover, when the ultraviolet curable adhesive composition of this invention is used for the use by which high adhesive physical property is required after heat-and-moisture resistance, it is preferable to contain a silane coupling agent. In addition, when the ultraviolet curable pressure-sensitive adhesive composition of the present invention is used for applications requiring high heat and heat yellowing resistance, it preferably contains an antioxidant and a light stabilizer.
前記有機溶剤としては、例えば、トルエン、酢酸エチル、酢酸ブチル、メチルエチルケトン、ヘキサン、アセトン、シクロヘキサノン、3−ペンタノン、アセトニトリル、プロピオニトリル、イソブチロニトリル、バレロニトリル、ジメチルスルホキシド、ジメチルホルムアミド等を用いることができる。これらの有機溶剤は単独で用いても2種以上を併用してもよい。 Examples of the organic solvent include toluene, ethyl acetate, butyl acetate, methyl ethyl ketone, hexane, acetone, cyclohexanone, 3-pentanone, acetonitrile, propionitrile, isobutyronitrile, valeronitrile, dimethyl sulfoxide, dimethylformamide, and the like. be able to. These organic solvents may be used alone or in combination of two or more.
前記有機溶剤を用いる場合の使用量としては、乾燥性及び塗工性をより一層向上できる点から、紫外線硬化型粘着剤組成物中60質量%以下であることが好ましく、5〜50質量%の範囲がより好ましい。 The amount used in the case of using the organic solvent is preferably 60% by mass or less in the ultraviolet curable pressure-sensitive adhesive composition from the viewpoint that drying property and coating property can be further improved, and 5 to 50% by mass. A range is more preferred.
前記シランカップリング剤としては、例えば、3−グリシドキシプロピルトリメトキシシラン、3−グリシドキシプロピルトリエトキシシラン、3−グリシドキシプロピルメチルジエトキシシラン、3−グリシドキシプロピルメチルジメトキシシラン等のエポキシ基を有するシランカップリング剤;2−(3,4−エポキシシクロヘキシル)エチルトリエトキシシラン、2−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン、2−(3,4−エポキシシクロヘキシル)エチルメチルジメトキシシラン、2−(3,4−エポキシシクロヘキシル)エチルメチルジエトキシシラン、2−(3,4−エポキシシクロヘキシル)プロピルトリメトキシシラン、2−(3,4−エポキシシクロヘキシル)プロピルメチルジメトキシシラン、2−(3,4−エポキシシクロヘキシル)プロピルトリエトキシシラン、2−(3,4−エポキシシクロヘキシル)プロピルメチルジエトキシシラン等の脂環エポキシ基を有するシランカップリング剤;ビニルトリクロルシラン、ビニルトリメトキシシラン、ビニルトリエトキシシラン、p−スチリルトリメトキシシラン、3−メタクリロキシプロピルメチルジメトキシシラン、3−メタクリロキシプロピルトリメトキシシラン、3−メタクリロキシプロピルメチルジエトキシシラン、3−メタクリロキシプロピルトリエトキシシラン、3−アクリロキシプロピルトリメトキシシラン、3−メルカプトプロピルメチルジメトキシシラン、3−メルカプトプロピルトリメトキシシラン、シリコーンアルコキシオリゴマーなどを用いることができる。これらのシランカップリング剤は単独で用いても2種以上を併用してもよい。これらの中でも、耐湿熱後の粘着力をより一層向上できる点から、エポキシ基を有するシランカップリング剤及び/又は脂環エポキシ基を有するシランカップリング剤を用いることが好ましく、2−(3,4−エポキシシクロヘキシル)エチルトリエトキシシラン、2−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン、3−グリシドキシプロピルトリメトキシシラン及び3−グリシドキシプロピルトリエトキシシランからなる群より選ばれる1種以上のシランカップリング剤を用いることがより好ましい。 Examples of the silane coupling agent include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, and 3-glycidoxypropylmethyldimethoxysilane. Silane coupling agents having an epoxy group such as 2- (3,4-epoxycyclohexyl) ethyltriethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ) Ethylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ethylmethyldiethoxysilane, 2- (3,4-epoxycyclohexyl) propyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) propylmethyldimethoxy Silane Silane coupling agents having an alicyclic epoxy group such as 2- (3,4-epoxycyclohexyl) propyltriethoxysilane and 2- (3,4-epoxycyclohexyl) propylmethyldiethoxysilane; vinyltrichlorosilane, vinyltrimethoxy Silane, vinyltriethoxysilane, p-styryltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane , 3-acryloxypropyltrimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, 3-mercaptopropyltrimethoxysilane, silicone alkoxy oligomer, etc. That. These silane coupling agents may be used alone or in combination of two or more. Among these, it is preferred to use a silane coupling agent having an epoxy group and / or a silane coupling agent having an alicyclic epoxy group from the viewpoint that the adhesive force after heat and humidity resistance can be further improved. 4-epoxycyclohexyl) ethyltriethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane and 3-glycidoxypropyltriethoxysilane It is more preferable to use one or more silane coupling agents.
前記シランカップリング剤を用いる場合の使用量としては、耐湿熱後の粘着力をより一層向上できる点から、前記ウレタン樹脂(A)100質量部に対して、0.01〜10質量部の範囲であることが好ましく、0.05〜5質量部の範囲がより好ましく、0.05〜1質量部の範囲が更に好ましい。 As the usage-amount in the case of using the said silane coupling agent, the range which is 0.01-10 mass parts with respect to 100 mass parts of said urethane resins (A) from the point which can improve the adhesive force after moisture-and-heat resistance further. The range of 0.05 to 5 parts by mass is more preferable, and the range of 0.05 to 1 part by mass is even more preferable.
前記酸化防止剤としては、熱劣化で発生するラジカルの捕捉するヒンダードフェノール化合物(一次酸化防止剤)、及び、熱劣化で発生する過酸化物を分解するリン化合物、イオウ化合物(二次酸化防止剤)等を用いることができる。 Examples of the antioxidant include hindered phenol compounds (primary antioxidants) that capture radicals generated by thermal degradation, phosphorus compounds that decompose peroxides generated by thermal degradation, and sulfur compounds (secondary antioxidants). Agent) and the like.
前記ヒンダードフェノール化合物としては、例えば、トリエチレングリコール−ビス−[3−(3−t−ブチル−5−メチル−4ヒドロキシフェニル)プロピオネート]、ペンタエリスリトールテトラキス[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート、オクタデシル[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート、チオジエチレンビス[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート]、ベンゼンプロパン酸−3,5−ビス(1,1−ジメチルエチル)−4−ヒドロキシ−C7−C9側鎖アルキルエステル、4,6−ビス(ドデシルチオメチル)−o−クレゾール、N−フェニルベンゼンアミンと2,4,4−トリメチルペンテンとの反応生成物、2−t−ブチル−6−(3−t−ブチル−2−ヒドロキシ−5−メチルベンジル)−4−メチルフェニルアクリレート、3,9−ビス[2−〔3−(t−ブチル−4−ヒドロキシ−5−メチルフェニル)プロピオニルオキシ〕−1,1−ジメチルエチル]2,4,8,10−テトラオキサスピロ〔5・5〕ウンデカン、2,6−ジ−tert−ブチル−4−メチルフェノール、2,2’−メチレンビス(4−メチル−6−tert−ブチルフェノール)、2,5−ジ−tert−アミルハイドロキノン等を用いることができる。これらの化合物は単独で用いても2種以上を併用してもよい。Examples of the hindered phenol compound include triethylene glycol-bis- [3- (3-tert-butyl-5-methyl-4hydroxyphenyl) propionate], pentaerythritol tetrakis [3- (3,5-di-). tert-butyl-4-hydroxyphenyl) propionate, octadecyl [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate, thiodiethylenebis [3- (3,5-di-tert-butyl- 4-hydroxyphenyl) propionate], benzenepropanoic acid-3,5-bis (1,1-dimethylethyl) -4-hydroxy-C 7 -C 9 side chain alkyl ester, 4,6-bis (dodecylthiomethyl) -O-cresol, N-phenylbenzenamine and 2,4,4-trimethylpente Product of 2-t-butyl-6- (3-t-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate, 3,9-bis [2- [3- (t -Butyl-4-hydroxy-5-methylphenyl) propionyloxy] -1,1-dimethylethyl] 2,4,8,10-tetraoxaspiro [5 · 5] undecane, 2,6-di-tert-butyl -4-methylphenol, 2,2'-methylenebis (4-methyl-6-tert-butylphenol), 2,5-di-tert-amylhydroquinone, and the like can be used. These compounds may be used alone or in combination of two or more.
前記リン化合物としては、例えば、トリフェニルホスフィン、ビス(2,4−ジ−tert−ブチル−6−メチルフェニル)=エチル=ホスフィット、トリフェニルホスファイト、トリスノニルフェニルホスファイト、トリス(2,4−ジブチルフェニル)ホスファイト、トリス(2,4−ジブチル−5−メチルフェニル)ホスファイト、トリス〔2−第三ブチル−4−(3−ブチル−4−ヒドロキシ−5−メチルフェニルチオ)−5−メチルフェニル〕ホスファイト、トリス(2,4−ジ−tert−ブチルフェニル)ホスファイト、トリデシルホスファイト、オクチルジフェニルホスファイト、ジ(デシル)モノフェニルホスファイト、ジ(トリデシル)ペンタエリスリトールジホスファイト、ジ(ノニルフェニル)ペンタエリスリトールジホスファイト、ビス(2,4−ジブチルフェニル)ペンタエリスリトールジホスファイト、ビス(2,6−ジブチル−4−メチルフェニル)ペンタエリスリトールジホスファイト、ビス(2,4,6−トリブチルフェニル)ペンタエリスリトールジホスファイト、ビス(2,4−ジクミルフェニル)ペンタエリスリトールジホスファイト、テトラ(トリデシル)イソプロピリデンジフェノールジホスファイト、テトラ(トリデシル)−4,4’−n−ブチリデンビス(2−ブチル−5−メチルフェノール)ジホスファイト、ヘキサ(トリデシル)−1,1,3−トリス(2−メチル−4−ヒドロキシ−5−ブチルフェニル)ブタントリホスファイト、テトラキス(2,4−ジブチルフェニル)ビフェニレンジホスホナイト、9,10−ジハイドロ−9−オキサ−10−ホスファフェナンスレン−10−オキサイド、2,2’−メチレンビス(4,6−ブチルフェニル)−2−エチルヘキシルホスファイト、2,2’−メチレンビス(4,6−ブチルフェニル)−オクタデシルホスファイト、2,2’−エチリデンビス(4,6−ジブチルフェニル)フルオロホスファイト、トリス(2−〔(2,4,8,10−テトラキスブチルジベンゾ〔d,f〕〔1,3,2〕ジオキサホスフェピン−6−イル)オキシ〕エチル)アミン、2−エチル−2−ブチルプロピレングリコールと2,4,6−トリブチルフェノールのホスファイト等を用いることができる。これらの化合物は単独で用いても2種以上を併用してもよい。 Examples of the phosphorus compound include triphenylphosphine, bis (2,4-di-tert-butyl-6-methylphenyl) = ethyl phosphite, triphenyl phosphite, trisnonylphenyl phosphite, tris (2, 4-dibutylphenyl) phosphite, tris (2,4-dibutyl-5-methylphenyl) phosphite, tris [2-tert-butyl-4- (3-butyl-4-hydroxy-5-methylphenylthio)- 5-methylphenyl] phosphite, tris (2,4-di-tert-butylphenyl) phosphite, tridecyl phosphite, octyl diphenyl phosphite, di (decyl) monophenyl phosphite, di (tridecyl) pentaerythritol di Phosphite, di (nonylphenyl) pentaerythritol Diphosphite, bis (2,4-dibutylphenyl) pentaerythritol diphosphite, bis (2,6-dibutyl-4-methylphenyl) pentaerythritol diphosphite, bis (2,4,6-tributylphenyl) pentaerythritol diphosphite Phosphite, bis (2,4-dicumylphenyl) pentaerythritol diphosphite, tetra (tridecyl) isopropylidene diphenol diphosphite, tetra (tridecyl) -4,4′-n-butylidenebis (2-butyl-5) -Methylphenol) diphosphite, hexa (tridecyl) -1,1,3-tris (2-methyl-4-hydroxy-5-butylphenyl) butane triphosphite, tetrakis (2,4-dibutylphenyl) biphenylene diphosphonite, 9,10-di Idro-9-oxa-10-phosphaphenanthrene-10-oxide, 2,2′-methylenebis (4,6-butylphenyl) -2-ethylhexyl phosphite, 2,2′-methylenebis (4,6- Butylphenyl) -octadecylphosphite, 2,2′-ethylidenebis (4,6-dibutylphenyl) fluorophosphite, tris (2-[(2,4,8,10-tetrakisbutyldibenzo [d, f] [ 1,3,2] dioxaphosphin-6-yl) oxy] ethyl) amine, 2-ethyl-2-butylpropylene glycol and 2,4,6-tributylphenol phosphite, and the like can be used. These compounds may be used alone or in combination of two or more.
前記イオウ化合物としては、例えば、ジドデシル−3,3’−チオプロピオネート、ジラウリル−3,3’−チオジプロピオネート、ラウジリルチオジチオネート、ジトリデシル−3,3’−チオジプロピオネート、ジミリスチル−3,3’−チオジプロピオネート、ジステアリル−3,3’−チオジプロピオネート、テトラキス−メチレン−3−ラウリルチオプロピオネートメタン、ジステアリル−3,3’−メチル−3,3’−チオジプロピオネート、ラウリルステアリル−3,3’−チオジプロピオネート、ビス[2−メチル−4−(3−n−アルキルチオプロピオニルオキシ)−5−t−ブチルフェニル]スルフィド、β−ラウリルチオプロピオネート、2−メルカプトベンゾイミダゾール、2−メルカプト−5−メチルベンゾイミダゾール、ジオクタデシル−3,3’−チオジプロチオネート等を用いることができる。これらの化合物は単独で用いても2種以上を併用してもよい。 Examples of the sulfur compound include didodecyl-3,3′-thiopropionate, dilauryl-3,3′-thiodipropionate, laurylthiothiothionate, ditridecyl-3,3′-thiodipropionate, Dimyristyl-3,3′-thiodipropionate, distearyl-3,3′-thiodipropionate, tetrakis-methylene-3-laurylthiopropionate methane, distearyl-3,3′-methyl-3, 3′-thiodipropionate, lauryl stearyl-3,3′-thiodipropionate, bis [2-methyl-4- (3-n-alkylthiopropionyloxy) -5-tert-butylphenyl] sulfide, β- Lauryl thiopropionate, 2-mercaptobenzimidazole, 2-mercapto-5-methylbenzimi Tetrazole, can be used dioctadecyl 3,3'-thio dipropionate isethionate, and the like. These compounds may be used alone or in combination of two or more.
これらの中でも、粘着力及び耐湿熱黄変性をより一層向上できる点から、リン化合物を用いることが好ましく、トリフェニルホスフィン、ビス(2,4−ジ−tert−ブチル−6−メチルフェニル)=エチル=ホスフィット及びトリス(2,4−ジ−tert−ブチルフェニル)ホスファイトからなる群より選ばれる1種以上の酸化防止剤を用いることがより好ましく、トリフェニルホスフィン、ビス(2,4−ジ−tert−ブチル−6−メチルフェニル)=エチル=ホスフィットを用いることがより好ましい。 Among these, it is preferable to use a phosphorus compound from the viewpoint of further improving adhesive strength and heat and heat yellowing resistance, and triphenylphosphine, bis (2,4-di-tert-butyl-6-methylphenyl) = ethyl. It is more preferable to use one or more antioxidants selected from the group consisting of phosphite and tris (2,4-di-tert-butylphenyl) phosphite, and triphenylphosphine and bis (2,4-di More preferably, -tert-butyl-6-methylphenyl) = ethyl = phosphite is used.
前記酸化防止剤を用いる場合の使用量としては、耐湿熱黄変性をより一層向上できる点から、前記ウレタン樹脂(A)100質量部に対して、0.01〜10質量部の範囲であることが好ましい。 The amount used in the case of using the antioxidant is in the range of 0.01 to 10 parts by mass with respect to 100 parts by mass of the urethane resin (A), from the point that moisture heat yellowing resistance can be further improved. Is preferred.
前記光安定剤は、光劣化で発生するラジカルを捕捉するものであり、例えば、チオール化合物、チオエーテル化合物、ヒンダードアミン化合物等のラジカル捕捉剤;ベンゾフェノン化合物、ベンゾエート化合物等の紫外線吸収剤などを用いることができる。これらの光安定剤は単独で用いても2種以上を併用してもよい。これらの中でも、耐湿熱黄変性をより一層向上できる点から、ヒンダードアミン化合物を用いることが好ましい。 The light stabilizer captures radicals generated by photodegradation. For example, a radical scavenger such as a thiol compound, a thioether compound, or a hindered amine compound; an ultraviolet absorber such as a benzophenone compound or a benzoate compound may be used. it can. These light stabilizers may be used alone or in combination of two or more. Among these, it is preferable to use a hindered amine compound from the viewpoint that the heat and heat yellowing resistance can be further improved.
前記ヒンダードアミン化合物としては、例えば、シクロヘキサンと過酸化N−ブチル2,2,6,6−テトラメチル−4−ピペリジンアミン−2,4,6−トリクロロ1,3,5−トリアジンとの反応生成物と2−アミノエタノールとの反応生成物、デカン二酸ビス(2,2,6,6−テトラメチル−1−(オクチルオキシ)−4−ピペリジニル)エステル、1,1−ジメチルエチルヒドロペルオキシドとオクタンの反応生成物等のアミノエーテル基を有するヒンダードアミン化合物;N−アセチル−3−ドデシル−1−(2,2,6,6−テトラメチル−4−ピペリジニル)ピロリジン−2,5−ジオン等のN−アセチル系ヒンダードアミン化合物;ビス(1,2,2,6,6−ペンタメチル−4−ピペリジル)=デカンジオアート、ビス(1,2,2,6,6,−ペンタメチル−4−ピペリジル){[3,5−ビス(1,1−ジメチルエチル)−4−ヒドロキシフェニル]メチル}ブチルマロネート、コハク酸ジメチル・1−(2−ヒドロキシエチル)−4−ヒドロキシ−2,2,6,6−テトラメチルピペリジン重縮合物、プロバンジオイックアシッド[{4−メトキシフェニル}メチレン]−ビス(1,2,2,6,6−ペンタメチル−4−ピペリジル)エステルのN−アルキルヒンダードアミン化合物等を用いることができる。これらの化合物は単独で用いても2種以上を併用してもよい。 Examples of the hindered amine compound include a reaction product of cyclohexane and N-butyl peroxide 2,2,6,6-tetramethyl-4-piperidineamine-2,4,6-trichloro 1,3,5-triazine. Product of 2-aminoethanol with decanedioic acid bis (2,2,6,6-tetramethyl-1- (octyloxy) -4-piperidinyl) ester, 1,1-dimethylethyl hydroperoxide and octane A hindered amine compound having an amino ether group such as a reaction product of N; N-acetyl-3-dodecyl-1- (2,2,6,6-tetramethyl-4-piperidinyl) pyrrolidine-2,5-dione and the like N -Acetyl hindered amine compound; bis (1,2,2,6,6-pentamethyl-4-piperidyl) = decanedioate, bis 1,2,2,6,6, -pentamethyl-4-piperidyl) {[3,5-bis (1,1-dimethylethyl) -4-hydroxyphenyl] methyl} butyl malonate, dimethyl succinate (2-Hydroxyethyl) -4-hydroxy-2,2,6,6-tetramethylpiperidine polycondensate, Provandioic acid [{4-methoxyphenyl} methylene] -bis (1,2,2,6, N-alkyl hindered amine compounds of 6-pentamethyl-4-piperidyl) ester and the like can be used. These compounds may be used alone or in combination of two or more.
前記光安定剤を用いる場合の使用量としては、耐湿熱黄変性をより一層向上できる点から、前記ウレタン樹脂(A)100質量部に対して、0.01〜10質量部の範囲であることが好ましい。 The amount used in the case of using the light stabilizer is in the range of 0.01 to 10 parts by mass with respect to 100 parts by mass of the urethane resin (A), from the point that moisture heat yellowing resistance can be further improved. Is preferred.
本発明の紫外線硬化型粘着剤組成物の粘度としては、塗工性及び作業性の点から、500〜30,000mPa・sの範囲であることが好ましく、1,000〜20,000mPa・sの範囲がより好ましい。なお、前記粘度は、25℃でB型粘度計にて測定した値を示す。 As a viscosity of the ultraviolet curable adhesive composition of this invention, it is preferable that it is the range of 500-30,000 mPa * s from the point of coating property and workability | operativity, and is 1,000-20,000 mPa * s. A range is more preferred. In addition, the said viscosity shows the value measured with the B-type viscometer at 25 degreeC.
本発明の粘着シートの製造方法としては、例えば、前記紫外線硬化型粘着剤組成物を被着体に塗工し、必要に応じて乾燥し、その後紫外線硬化することにより製造する方法が挙げられる。 Examples of the method for producing the pressure-sensitive adhesive sheet of the present invention include a method for producing the pressure-sensitive adhesive composition by applying the UV-curable pressure-sensitive adhesive composition to an adherend, drying it if necessary, and then UV-curing it.
前記被着体としては、例えば、プラスチック基材、フレキシブルプリント基材、これらの基材に離型処理を施した基材やITO(酸化インジウム錫)を蒸着した基材;ガラス板、鋼板、亜鉛鋼板、ブリキ板、アルミニウム板等の高極性な基材を用いることができる。なお、粘着層の両面にはそれぞれ同一の基材を用いても別々の基材を用いてもよい。 Examples of the adherend include a plastic substrate, a flexible printed substrate, a substrate obtained by subjecting these substrates to a release treatment, and a substrate obtained by vapor deposition of ITO (indium tin oxide); glass plate, steel plate, zinc A highly polar base material such as a steel plate, a tin plate, or an aluminum plate can be used. In addition, the same base material may be used for both surfaces of the adhesion layer, or different base materials may be used.
前記プラスチック基材としては、例えば、アクリル樹脂、PC(ポリカーボネート)、PBT(ポリブチレンテレフタレート)、PPS(ポリフェニレンサルファイド)、変性PPE(ポリフェニレンエーテル)、PET(ポリエチレンテレフタレート)、COP(シクロオレフィンポリマー)、TAC(トリアセチルセルロース)等を原料として得られるプラスチックフィルム、反射防止フィルム、防汚フィルム、タッチパネルを構成する透明導電膜のフィルム等を用いることができる。 Examples of the plastic substrate include acrylic resin, PC (polycarbonate), PBT (polybutylene terephthalate), PPS (polyphenylene sulfide), modified PPE (polyphenylene ether), PET (polyethylene terephthalate), COP (cycloolefin polymer), A plastic film obtained by using TAC (triacetylcellulose) or the like as a raw material, an antireflection film, an antifouling film, a transparent conductive film constituting a touch panel, or the like can be used.
前記紫外線硬化型粘着剤組成物を前記基材に塗工する方法としては、例えば、アプリケーター、ロールコーター、ナイフコーター、グラビアコーター等を使用して塗布する方法が挙げられる。前記塗工後は、乾燥を行う場合は得られた積層体を乾燥機等に入れ、例えば温度50〜130℃の範囲で、1〜30分乾燥させる方法が挙げられる。 Examples of the method of applying the ultraviolet curable pressure-sensitive adhesive composition to the substrate include a method of applying using an applicator, a roll coater, a knife coater, a gravure coater and the like. After the coating, when drying is performed, the obtained laminate is put in a dryer or the like, and dried at a temperature of 50 to 130 ° C. for 1 to 30 minutes, for example.
その後、紫外線照射することにより粘着シートが得られるが、前記紫外線照射する方法としては、例えば、キセノンランプ、キセノン−水銀ランプ、メタルハライドランプ、高圧水銀ランプ、低圧水銀ランプ等の公知の紫外線光照射装置を用いる方法が挙げられる。 Thereafter, an adhesive sheet is obtained by irradiating with ultraviolet rays. Examples of the method of irradiating with ultraviolet rays include known ultraviolet light irradiation devices such as a xenon lamp, a xenon-mercury lamp, a metal halide lamp, a high-pressure mercury lamp, and a low-pressure mercury lamp. The method using is mentioned.
前記紫外線の照射量としては、好ましくは0.05〜5J/cm2、より好ましくは0.1〜3J/cm2、特に好ましくは0.3〜1.5J/cm2の範囲であることがよい。なお、紫外線の照射量は、GSユアサ株式会社製UVチェッカー「UVR−N1」を用いて300〜390nmの波長域において測定した値を基準とする。The irradiation amount of the ultraviolet rays is preferably 0.05 to 5 J / cm 2 , more preferably 0.1 to 3 J / cm 2 , and particularly preferably 0.3 to 1.5 J / cm 2. Good. In addition, the irradiation amount of an ultraviolet-ray is based on the value measured in 300-390 nm wavelength range using UV checker "UVR-N1" by GS Yuasa Co., Ltd.
以上の方法にして得られる粘着シートの厚さとしては、使用される用途に応じて適宜決定されるが、例えば10〜500μmの範囲である。 The thickness of the pressure-sensitive adhesive sheet obtained by the above method is appropriately determined according to the intended use, and is, for example, in the range of 10 to 500 μm.
以上、本発明の紫外線硬化型粘着剤組成物は、熱架橋及び紫外線硬化を併用し得るものであり、金属板やガラス板等の高極性な被着体への密着性及び耐湿熱白化性に優れるものである。 As described above, the ultraviolet curable pressure-sensitive adhesive composition of the present invention can be used in combination with thermal crosslinking and ultraviolet curing, and can adhere to a highly polar adherend such as a metal plate or a glass plate and can be resistant to heat and heat whitening. It is excellent.
従って、本発明の紫外線硬化型粘着剤組成物は、医療用、文具用、光学部材用等の様々分野で好適に使用することができる。 Accordingly, the ultraviolet curable pressure-sensitive adhesive composition of the present invention can be suitably used in various fields such as medical use, stationery use, and optical member use.
以下、実施例を用いて、本発明をより詳細に説明する。 Hereinafter, the present invention will be described in more detail with reference to examples.
[合成例1]
<ウレタン樹脂(A−1)の合成>
攪拌機、還流冷却管、窒素導入管、温度計を備えた反応容器に、ポリプロピレングリコール(数平均分子量;1,000、以下「PPG」と略記する。)を194質量部、1,4−シクロヘキサンジメタノール(以下「CHDM」と略記する。)を39.4質量部、グリセリンモノメタクリレート(日油株式会社「ブレンマーGLM」、以下「GLM」と略記する。)を5.5質量部、2,6−ジ−ターシャリーブチル−クレゾールを1質量部、p−メトキシフェノールを0.5質量部添加した。反応容器内温度が40℃になるまで昇温した後、イソホロンジイソシアネート(以下「IPDI」と略記する。)を109質量部添加した。そこで、ジオクチルスズジネオデカネート0.1質量部添加し、1時間かけて80℃まで昇温した。その後、80℃で12時間ホールドし、全てのイソシアネート基が消失していることを確認後、冷却しウレタン樹脂(A−1)を得た。得られたウレタン樹脂(A−1)は、重量平均分子量が40,400、アクリロイル基の含有量が0.1mol/kgであった。[Synthesis Example 1]
<Synthesis of Urethane Resin (A-1)>
In a reaction vessel equipped with a stirrer, a reflux condenser, a nitrogen inlet tube, and a thermometer, 194 parts by mass of polypropylene glycol (number average molecular weight; 1,000, hereinafter abbreviated as “PPG”), 1,4-cyclohexanedi 39.4 parts by mass of methanol (hereinafter abbreviated as “CHDM”), 5.5 parts by mass of glycerin monomethacrylate (“Nippon Corporation“ Blenmer GLM ”, hereinafter abbreviated as“ GLM ”), 2, 6 -1 part by mass of di-tertiary butyl-cresol and 0.5 part by mass of p-methoxyphenol were added. After raising the temperature in the reaction vessel to 40 ° C., 109 parts by mass of isophorone diisocyanate (hereinafter abbreviated as “IPDI”) was added. Therefore, 0.1 part by mass of dioctyltin dineodecanate was added, and the temperature was raised to 80 ° C. over 1 hour. Then, after hold | maintaining at 80 degreeC for 12 hours and confirming that all the isocyanate groups have lose | disappeared, it cooled and obtained urethane resin (A-1). The obtained urethane resin (A-1) had a weight average molecular weight of 40,400 and an acryloyl group content of 0.1 mol / kg.
[合成例2]
<ウレタン樹脂(A−2)の合成>
撹拌機、還流冷却管、窒素導入管、温度計を備えた反応容器に、ポリオキシテトラメチレングリコール(数平均分子量;1,000、以下「PTMG」と略記する。)を259質量部、1,4−ブタンジオール(以下、「1,4BG」と略記する。)を19質量部、GLMを6.2質量部、2,6−ジ−ターシャリーブチル−クレゾールを1質量部、p−メトキシフェノールを0.5質量部添加した。反応容器内温度が40℃になるまで昇温した後、IPDIを110質量部添加した。そこで、ジオクチルスズジネオデカネート0.1質量部添加し、1時間かけて80℃まで昇温した。その後、80℃で12時間ホールドし、全てのイソシアネート基が消失していることを確認後、冷却しウレタン樹脂(A−2)を得た。得られたウレタン樹脂(A−2)は、重量平均分子量が56,000、アクリロイル基の含有量が0.1mol/kgであった。[Synthesis Example 2]
<Synthesis of Urethane Resin (A-2)>
In a reaction vessel equipped with a stirrer, a reflux condenser, a nitrogen inlet tube, and a thermometer, 259 parts by mass of polyoxytetramethylene glycol (number average molecular weight; 1,000, hereinafter abbreviated as “PTMG”), 19 parts by mass of 4-butanediol (hereinafter abbreviated as “1,4BG”), 6.2 parts by mass of GLM, 1 part by mass of 2,6-ditertiarybutyl-cresol, p-methoxyphenol Was added in an amount of 0.5 parts by mass. After raising the temperature in the reaction vessel to 40 ° C., 110 parts by mass of IPDI was added. Therefore, 0.1 part by mass of dioctyltin dineodecanate was added, and the temperature was raised to 80 ° C. over 1 hour. Then, after hold | maintaining at 80 degreeC for 12 hours and confirming that all the isocyanate groups have lose | disappeared, it cooled and obtained urethane resin (A-2). The obtained urethane resin (A-2) had a weight average molecular weight of 56,000 and an acryloyl group content of 0.1 mol / kg.
[合成例3]
<ウレタン樹脂(A−3)の合成>
撹拌機、還流冷却管、窒素導入管、温度計を備えた反応容器に、ポリカーボネートポリオール(旭化成ケミカルズ株式会社製「デュラネートT5651」、数平均分子量;1,000、以下「PC」と略記する。)を256質量部、CHDMを33質量部、GLMを3.2質量部、2,6−ジ−ターシャリーブチル−クレゾールを1質量部、p−メトキシフェノールを0.5質量部添加した。反応容器内温度が40℃になるまで昇温した後、IPDIを109質量部添加した。そこで、ジオクチルスズジネオデカネート0.1質量部添加し、1時間かけて80℃まで昇温した。その後、80℃で12時間ホールドし、全てのイソシアネート基が消失していることを確認後、冷却しウレタン樹脂(A−3)を得た。得られたウレタン樹脂(A−3)は、重量平均分子量が39,500、アクリロイル基の含有量が0.05mol/kgであった。[Synthesis Example 3]
<Synthesis of Urethane Resin (A-3)>
Polycarbonate polyol ("Duranate T5651" manufactured by Asahi Kasei Chemicals Corporation, number average molecular weight; 1,000, hereinafter abbreviated as "PC") in a reaction vessel equipped with a stirrer, reflux condenser, nitrogen inlet tube, and thermometer. Was added in an amount of 256 parts by mass, 33 parts by mass of CHDM, 3.2 parts by mass of GLM, 1 part by mass of 2,6-ditertiarybutyl-cresol, and 0.5 parts by mass of p-methoxyphenol. After raising the temperature in the reaction vessel to 40 ° C., 109 parts by mass of IPDI was added. Therefore, 0.1 part by mass of dioctyltin dineodecanate was added, and the temperature was raised to 80 ° C. over 1 hour. Then, after hold | maintaining at 80 degreeC for 12 hours and confirming that all the isocyanate groups have lose | disappeared, it cooled and obtained urethane resin (A-3). The obtained urethane resin (A-3) had a weight average molecular weight of 39,500 and an acryloyl group content of 0.05 mol / kg.
[合成例5]
<ウレタン樹脂(A−4)の合成>
撹拌機、還流冷却管、窒素導入管、温度計を備えた反応容器に、PPGを217質量部、CHDMを27.5質量部、GLMを15.3質量部、2,6−ジ−ターシャリーブチル−クレゾールを1質量部、p−メトキシフェノールを0.5質量部添加した。反応容器内温度が40℃になるまで昇温した後、IPDIを110質量部添加した。そこで、ジオクチルスズジネオデカネート0.1質量部添加し、1時間かけて80℃まで昇温した。その後、80℃で12時間ホールドし、全てのイソシアネート基が消失していることを確認後、冷却しウレタン樹脂(A−4)を得た。得られたウレタン樹脂(A−4)は、重量平均分子量が42,000、アクリロイル基の含有量が0.25mol/kgであった。[Synthesis Example 5]
<Synthesis of Urethane Resin (A-4)>
In a reaction vessel equipped with a stirrer, a reflux condenser, a nitrogen inlet tube, and a thermometer, 217 parts by mass of PPG, 27.5 parts by mass of CHDM, 15.3 parts by mass of GLM, 2,6-ditertiary 1 part by mass of butyl-cresol and 0.5 part by mass of p-methoxyphenol were added. After raising the temperature in the reaction vessel to 40 ° C., 110 parts by mass of IPDI was added. Therefore, 0.1 part by mass of dioctyltin dineodecanate was added, and the temperature was raised to 80 ° C. over 1 hour. Then, after hold | maintaining at 80 degreeC for 12 hours and confirming that all the isocyanate groups have lose | disappeared, it cooled and obtained urethane resin (A-4). The obtained urethane resin (A-4) had a weight average molecular weight of 42,000 and an acryloyl group content of 0.25 mol / kg.
[実施例1]
<紫外線硬化型粘着剤組成物の調製>
攪拌機、還流冷却管、温度計を備えた反応容器に、前記ウレタン樹脂(A−1)100質量部、2,4,6−トリメチルベンゾイルジフェニル−フォスフィンオキサイド(以下「(B−1)」と略記する。)を0.5質量部、デカン二酸ビス(2,2,6,6−テトラメチル−1−(オクチルオキシ)−4−ピペリジニル)エステルを0.5質量部、トリフェニルフォスフィン0.5質量部を順次添加し、均一になるまで撹拌した。その後、200メッシュ金網で濾過し、紫外線硬化型粘着剤組成物を得た。[Example 1]
<Preparation of UV-curable adhesive composition>
In a reaction vessel equipped with a stirrer, a reflux condenser, and a thermometer, 100 parts by mass of the urethane resin (A-1), 2,4,6-trimethylbenzoyldiphenyl-phosphine oxide (hereinafter referred to as “(B-1)”) 0.5 parts by mass of decanedioic acid bis (2,2,6,6-tetramethyl-1- (octyloxy) -4-piperidinyl) ester, 0.5 parts by mass of triphenylphosphine 0.5 parts by mass were sequentially added and stirred until uniform. Thereafter, the mixture was filtered through a 200 mesh wire net to obtain an ultraviolet curable pressure-sensitive adhesive composition.
[実施例2〜4]
用いるウレタン樹脂(A)の種類を表1に示す通りに変更した以外は実施例1と同様にして紫外線硬化型粘着剤組成物を得た。[Examples 2 to 4]
An ultraviolet curable pressure-sensitive adhesive composition was obtained in the same manner as in Example 1 except that the type of the urethane resin (A) used was changed as shown in Table 1.
[比較合成例1]
<ウレタン樹脂(A’−1)の合成>
攪拌機、還流冷却管、窒素導入管、温度計を備えた反応容器に、PPGを205質量部、CHDMを42質量部、2−ヒドロキシエチルアクリレート(以下「HEA」と略記する。)1.3質量部、2,6−ジ−ターシャリーブチル−クレゾールを0.5質量部、p−メトキシフェノール0.1質量部を添加した。反応容器内温度が40℃になるまで昇温した後、IPDIを110質量部添加した。そこで、ジオクチルスズジネオデカネート0.1質量部添加し、1時間かけて80℃まで昇温した。その後、80℃で12時間ホールドし、全てのイソシアネート基が消失していることを確認後、冷却しウレタン樹脂(A’−1)を得た。得られたウレタン樹脂(A’−1)は、重量平均分子量が29,000、アクリロイル基の含有量が0.03mol/kgであった。[Comparative Synthesis Example 1]
<Synthesis of Urethane Resin (A′-1)>
In a reaction vessel equipped with a stirrer, a reflux condenser, a nitrogen inlet tube, and a thermometer, 205 parts by mass of PPG, 42 parts by mass of CHDM, and 1.3 parts by mass of 2-hydroxyethyl acrylate (hereinafter abbreviated as “HEA”). Part, 0.5 part by mass of 2,6-ditertiarybutyl-cresol and 0.1 part by mass of p-methoxyphenol were added. After raising the temperature in the reaction vessel to 40 ° C., 110 parts by mass of IPDI was added. Therefore, 0.1 part by mass of dioctyltin dineodecanate was added, and the temperature was raised to 80 ° C. over 1 hour. Then, after hold | maintaining at 80 degreeC for 12 hours and confirming that all the isocyanate groups have lose | disappeared, it cooled and obtained urethane resin (A'-1). The obtained urethane resin (A′-1) had a weight average molecular weight of 29,000 and an acryloyl group content of 0.03 mol / kg.
[比較例1]
ウレタン樹脂(A−1)の代わりに、比較合成例1で得られたウレタン樹脂(A’−1)を用いた以外は、実施例1と同様にして紫外線硬化型組成物を得た。[Comparative Example 1]
An ultraviolet curable composition was obtained in the same manner as in Example 1 except that the urethane resin (A′-1) obtained in Comparative Synthesis Example 1 was used instead of the urethane resin (A-1).
[各種被着体への密着性の評価方法]
表面に離型処理された厚さ50μmのポリエチレンテレフタレートフィルム(離型PET50)の表面に、有機溶剤乾燥後の膜厚が100μmとなるように実施例及び比較例で得られた紫外線硬化型粘着剤脂組成物を塗布し、80℃乾燥機中で3分間乾燥させた後に厚さ100μmのPETフィルムを貼り合せた。次いで、離型PETを剥離し、被着体であるガラス板及び鋼板に2kgローラー×2往復で貼り合せ、PETフィルム透過後のUV−A領域の波長の積算光量が1J/cm2となるように紫外線照射し、試験片を得た。次いで、得られた試験片をクロスカット法(JISK5600−5−6−1999)により、各種被着体に対する密着性を以下の基準で評価した。なお、前記クロスカット試験では、ポリエステル粘着テープ(日東電工株式会社製「N0.31B」)を使用した。
「T」;被着体上に残存した粘着剤層のマス目が100個であった。
「F」;被着体上に残存した粘着剤層のマス目が99個以下であった。[Method for evaluating adhesion to various adherends]
UV curable pressure-sensitive adhesives obtained in Examples and Comparative Examples so that the film thickness after drying the organic solvent is 100 μm on the surface of a 50 μm-thick polyethylene terephthalate film (release PET 50) having a release treatment on the surface. The fat composition was applied, dried in an 80 ° C. dryer for 3 minutes, and then a 100 μm thick PET film was bonded. Next, the release PET is peeled off and bonded to the glass plate and the steel plate, which are adherends, with a 2 kg roller × 2 reciprocation, so that the integrated light quantity of the wavelength in the UV-A region after passing through the PET film becomes 1 J / cm 2. Were irradiated with ultraviolet rays to obtain test pieces. Subsequently, the adhesiveness with respect to various to-be-adhered bodies was evaluated by the following reference | standard for the obtained test piece with the cross-cut method (JISK5600-5-6-1999). In the cross-cut test, a polyester adhesive tape (“N0.31B” manufactured by Nitto Denko Corporation) was used.
“T”: 100 squares of the pressure-sensitive adhesive layer remained on the adherend.
“F”: The number of grids of the pressure-sensitive adhesive layer remaining on the adherend was 99 or less.
[耐湿熱白化性の評価方法]
表面に離型処理された厚さ50μmのポリエチレンテレフタレートフィルム(離型PET50)の表面に、有機溶剤乾燥後の膜厚が100μmとなるように実施例及び比較例で得られた紫外線硬化型粘着剤脂組成物を塗布し、80℃乾燥機中で3分間乾燥させた後に離型PETを貼り合せた。これを縦50mm、横40mmに裁断した。その後、ガラス板透過後のUV−A領域の波長の積算光量が1J/cm2となるように紫外線照射し、粘着シートを有する積層体を得、試験片とした。該試験片のヘイズ(%)を濁度計「NDH5000」(日本電色工業(株)製)にて、JISK7361−1−1997に準じて測定した。次いで、得られた試験片を85℃、85%RHの条件下で100時間放置した後(以下、「耐湿熱試験後」と略記する。)、23℃、50%RHの雰囲気下で取り出した。取り出し後、10分以内にヘイズ(%)を濁度計「NDH5000」(日本電色工業(株)製)にて、JISK7361−1−1997に準じて測定し、耐湿熱白化性を以下のように評価した。
「T」:耐湿熱試験前後のヘイズ(%)値の差が1%未満である。
「F」:耐湿熱試験前後のヘイズ(%)値の差が1%以上である。[Evaluation method for resistance to moist heat whitening]
UV curable pressure-sensitive adhesives obtained in Examples and Comparative Examples so that the film thickness after drying the organic solvent is 100 μm on the surface of a 50 μm-thick polyethylene terephthalate film (release PET 50) having a release treatment on the surface. The fat composition was applied and dried in an 80 ° C. dryer for 3 minutes, and then release PET was bonded. This was cut into 50 mm length and 40 mm width. Then, ultraviolet rays were irradiated so that the integrated light quantity of the wavelength of the UV-A area | region after permeation | transmission of a glass plate might be 1 J / cm < 2 >, the laminated body which has an adhesive sheet was obtained, and it was set as the test piece. The haze (%) of the test piece was measured with a turbidimeter “NDH5000” (manufactured by Nippon Denshoku Industries Co., Ltd.) according to JIS K7361-1-1997. Next, the obtained test piece was allowed to stand for 100 hours under the conditions of 85 ° C. and 85% RH (hereinafter abbreviated as “after wet heat resistance test”), and then taken out in an atmosphere of 23 ° C. and 50% RH. . Within 10 minutes after removal, the haze (%) was measured with a turbidimeter “NDH5000” (manufactured by Nippon Denshoku Industries Co., Ltd.) according to JIS K 7361-1-1997. Evaluated.
“T”: The difference in haze (%) value before and after the wet heat resistance test is less than 1%.
“F”: The difference in haze (%) values before and after the wet heat resistance test is 1% or more.
本発明の紫外線硬化型粘着剤組成物である実施例1〜5は、耐湿熱白化性、並びに、高極性な被着体であるガラス板及び鋼板に対する密着性に優れることが分かった。 It turned out that Examples 1-5 which are the ultraviolet curable adhesive compositions of this invention are excellent in heat-and-moisture whitening resistance, and the adhesiveness with respect to the glass plate and steel plate which are a highly polar adherend.
一方、比較例1は、(メタ)アクリル化合物(a3)の代わりにHEAを用いて、末端にアクリロイル基を導入したウレタン樹脂を用いた態様であるが、耐湿熱白化性が不良であり、また、ガラス板及び鋼板に対する密着性も不良であった。 On the other hand, Comparative Example 1 is an embodiment that uses HEA instead of the (meth) acrylic compound (a3) and a urethane resin into which an acryloyl group is introduced at the terminal, but has poor moisture and heat whitening resistance. Also, the adhesion to glass plates and steel plates was poor.
Claims (5)
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JPWO2019073979A1 (en) * | 2017-10-11 | 2020-11-26 | セメダイン株式会社 | Photocurable pressure-sensitive adhesive composition and bonding method |
CN113366078B (en) * | 2019-06-06 | 2023-06-23 | Dic株式会社 | Adhesive composition and surface protective film |
CN110256973B (en) * | 2019-07-23 | 2021-12-07 | 韦尔通(厦门)科技股份有限公司 | Dual-curing silane modified polyether adhesive, preparation method and use method thereof, and electric appliance product |
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