WO2018225430A1 - 紫外線硬化型シリコーン粘着剤組成物およびその硬化物 - Google Patents
紫外線硬化型シリコーン粘着剤組成物およびその硬化物 Download PDFInfo
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- WO2018225430A1 WO2018225430A1 PCT/JP2018/017581 JP2018017581W WO2018225430A1 WO 2018225430 A1 WO2018225430 A1 WO 2018225430A1 JP 2018017581 W JP2018017581 W JP 2018017581W WO 2018225430 A1 WO2018225430 A1 WO 2018225430A1
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- parts
- mass
- adhesive composition
- organopolysiloxane
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 43
- 239000013464 silicone adhesive Substances 0.000 title abstract description 4
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 57
- -1 acrylate compound Chemical class 0.000 claims abstract description 55
- 229920005989 resin Polymers 0.000 claims abstract description 8
- 239000011347 resin Substances 0.000 claims abstract description 8
- 239000003999 initiator Substances 0.000 claims abstract description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 22
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 229910004283 SiO 4 Inorganic materials 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 150000002430 hydrocarbons Chemical group 0.000 abstract description 15
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229910020485 SiO4/2 Inorganic materials 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 239000000047 product Substances 0.000 description 24
- 239000000853 adhesive Substances 0.000 description 16
- 230000001070 adhesive effect Effects 0.000 description 16
- 239000000463 material Substances 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 238000000576 coating method Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 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 description 4
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000004386 diacrylate group Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000006459 hydrosilylation reaction Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 2
- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 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
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 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
- 238000002156 mixing Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000004382 potting Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 238000010023 transfer printing Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- OBNIRVVPHSLTEP-UHFFFAOYSA-N 1-ethoxy-2-(2-hydroxyethoxy)ethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(O)COCCO OBNIRVVPHSLTEP-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- IAMASUILMZETHW-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.OCCOCC(O)OC1=CC=CC=C1 IAMASUILMZETHW-UHFFFAOYSA-N 0.000 description 1
- OADIZUFHUPTFAG-UHFFFAOYSA-N 2-[2-(2-ethylhexoxy)ethoxy]ethanol Chemical compound CCCCC(CC)COCCOCCO OADIZUFHUPTFAG-UHFFFAOYSA-N 0.000 description 1
- COORVRSSRBIIFJ-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]-1-methoxyethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(O)COCCOCCO COORVRSSRBIIFJ-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 1
- ZVYGIPWYVVJFRW-UHFFFAOYSA-N 3-methylbutyl prop-2-enoate Chemical compound CC(C)CCOC(=O)C=C ZVYGIPWYVVJFRW-UHFFFAOYSA-N 0.000 description 1
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- PSGCQDPCAWOCSH-BREBYQMCSA-N [(1r,3r,4r)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] prop-2-enoate Chemical compound C1C[C@@]2(C)[C@H](OC(=O)C=C)C[C@@H]1C2(C)C PSGCQDPCAWOCSH-BREBYQMCSA-N 0.000 description 1
- 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 1
- VKPVUNFNWSJTBJ-UHFFFAOYSA-N [dimethyl(trimethylsilyloxy)silyl]methyl prop-2-enoate Chemical compound C[Si](C)(C)O[Si](C)(C)COC(=O)C=C VKPVUNFNWSJTBJ-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 125000005998 bromoethyl group Chemical group 0.000 description 1
- 238000003426 chemical strengthening reaction Methods 0.000 description 1
- YGHUUVGIRWMJGE-UHFFFAOYSA-N chlorodimethylsilane Chemical compound C[SiH](C)Cl YGHUUVGIRWMJGE-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- UWGIJJRGSGDBFJ-UHFFFAOYSA-N dichloromethylsilane Chemical compound [SiH3]C(Cl)Cl UWGIJJRGSGDBFJ-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 239000004715 ethylene vinyl alcohol Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- RZXDTJIXPSCHCI-UHFFFAOYSA-N hexa-1,5-diene-2,5-diol Chemical compound OC(=C)CCC(O)=C RZXDTJIXPSCHCI-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 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
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 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
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- 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
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
-
- 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
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
-
- 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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
- C08F283/124—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes on to polysiloxanes having carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/10—Adhesives in the form of films or foils without carriers
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/442—Block-or graft-polymers containing polysiloxane sequences containing vinyl polymer sequences
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- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature
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- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation
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- 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
- C09J2433/00—Presence of (meth)acrylic polymer
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- 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
- C09J2483/00—Presence of polysiloxane
Definitions
- the present invention relates to an ultraviolet curable silicone pressure-sensitive adhesive composition and a cured product thereof, and more specifically, an ultraviolet curable silicone pressure-sensitive adhesive composition and a cured product thereof that can be suitably used as a temporary fixing material for transferring an object. About.
- Non-Patent Document 1 a technology capable of selectively transferring such miniaturized elements and components at a time has been developed and attracts attention.
- This technique is called a micro transfer printing technique, and is a technique in which fine parts are picked up with the adhesive strength of an elastomer and transferred to a desired place having a higher adhesive strength.
- Silicone elastomer is known as an adhesive material used for this purpose, and many heat-curable solventless silicone adhesives have been proposed (Patent Documents 1 to 3).
- Patent Documents 1 to 3 When a thermosetting silicone-based pressure-sensitive adhesive is used, energy is required because a heating step is essential, and much time is required for heating and cooling the material.
- Patent Document 4 In order to omit such a process, development of a silicone resin that can be cured with ultraviolet rays in a short time has also been undertaken (Patent Document 4). There was a problem that it was insufficient and applicable elements and parts were limited. Therefore, an ultraviolet curable adhesive silicone material having a stronger adhesive force that can be applied to elements and parts that cannot be lifted by the material of Patent Document 4 is desired.
- the present invention has been made in view of the above circumstances, and has an ultraviolet curable silicone pressure-sensitive adhesive composition that provides a cured product having good workability and curability and excellent tackiness and strength as a temporary fixing material, and the cured product thereof.
- the purpose is to provide.
- organopolysiloxane having a specific (meth) acryloyloxy-containing group, monofunctional (meth) acrylate compound and / or siloxane not containing siloxane structure By using a polyfunctional (meth) acrylate compound not containing a structure and a predetermined organopolysiloxane resin, an ultraviolet curable silicone composition that cures rapidly by ultraviolet irradiation and has good adhesiveness and strength can be obtained. As a result, the present invention has been completed.
- the ultraviolet curable silicone pressure-sensitive adhesive composition of the present invention has good workability and curability, and the cured product has excellent tackiness and strength as a temporary fixing material.
- the ultraviolet curable silicone pressure-sensitive adhesive composition according to the present invention is (A) organopolysiloxane having two groups represented by the following general formula (1) in one molecule: 100 parts by mass, One or both of (B) a monofunctional (meth) acrylate compound not containing a siloxane structure and (C) a polyfunctional (meth) acrylate compound not containing a siloxane structure: 1 to 500 parts by mass, (D) (a) R 4 3 SiO 1/2 unit (wherein R 4 represents an unsubstituted or substituted monovalent hydrocarbon group having 1 to 10 carbon atoms) and (b) SiO 4 / Organopolysiloxane resin consisting of 2 units and having a molar ratio of (a) unit to (b) unit in the range of 0.6 to 1.2: 1: 1 to 5000 parts by mass, and (E) photopolymerization initiation Agent: It is characterized by containing 0.01 to 20 parts by mass
- the component (A) used in the present invention is a crosslinking component of the present composition, has two groups represented by the following general formula (1) in one molecule, and the main chain is An organopolysiloxane consisting essentially of repeating diorganosiloxane units.
- R 1 independently of each other is a monovalent hydrocarbon group having 1 to 20 carbon atoms, preferably excluding an aliphatic unsaturated group, and having 1 to 10 carbon atoms, more preferably 1 to 1 carbon atom.
- 8 represents a monovalent hydrocarbon group
- R 2 represents an oxygen atom or an alkylene group having 1 to 20, preferably 1 to 10, more preferably 1 to 5 carbon atoms
- R 3 represents an acryloyloxyalkyl group.
- the monovalent hydrocarbon group having 1 to 20 carbon atoms of R 1 may be linear, branched or cyclic, and specific examples thereof include methyl, ethyl, n-propyl, isopropyl, alkyl groups such as n-butyl, isobutyl, tert-butyl, n-hexyl, cyclohexyl, n-octyl, 2-ethylhexyl, n-decyl group; vinyl, allyl (2-propenyl), 1-propenyl, isopropenyl, butenyl Alkenyl groups such as groups; aryl groups such as phenyl, tolyl, xylyl, and naphthyl groups; and aralkyl groups such as benzyl, phenylethyl, and phenylpropyl groups.
- some or all of the hydrogen atoms bonded to the carbon atoms of these monovalent hydrocarbon groups may be substituted with other substituents.
- substituents include chloromethyl, bromoethyl, trifluoropropyl, A halogen-substituted hydrocarbon group such as a cyanoethyl group, a cyano-substituted hydrocarbon group, and the like can be given.
- R 1 an alkyl group having 1 to 5 carbon atoms and a phenyl group are preferable, and a methyl group, an ethyl group, and a phenyl group are more preferable.
- the alkylene group of 1 to 20 carbon atoms of R 2 may be linear, branched or cyclic, and specific examples thereof include methylene, ethylene, propylene, trimethylene, tetramethylene, isobutylene, pentamethylene, hexamethylene. Examples include methylene, heptamethylene, octamethylene, nonamethylene and decylene groups. Among these, R 2, an oxygen atom, a methylene, ethylene, propylene group is preferable, an oxygen atom or an ethylene group is more preferable.
- the carbon number of the alkyl (alkylene) group in the acryloyloxyalkyl group, methacryloyloxyalkyl group, acryloyloxyalkyloxy group, or methacryloyloxyalkyloxy group of R 3 is not particularly limited, but 1 to 10 is preferable, and 1 to 5 is more preferable.
- Specific examples of these alkyl groups include those having 1 to 10 carbon atoms among the groups exemplified for R 1 above.
- Specific examples of R 3 include, but are not limited to, those represented by the following formula.
- p represents a number satisfying 0 ⁇ p ⁇ 10, preferably 0 or 1
- a represents a number satisfying 1 ⁇ a ⁇ 3, but preferably 1 or 2.
- the bonding position of the group represented by the general formula (1) may be a molecular chain non-terminal (that is, in the middle of a molecular chain or a molecule). Although it may be a chain side chain) or both of them, it is desirable that it exists only at the terminal in terms of flexibility.
- examples of the organic group bonded to the silicon atom other than the group represented by the general formula (1) include the same groups as the above R 1.
- a monovalent hydrocarbon group having 1 to 12 carbon atoms, preferably 1 to 10 carbon atoms, excluding unsaturated groups is suitable. Specific examples thereof include the same groups as those exemplified above for R 1 , but an alkyl group, an aryl group, and a halogenated alkyl group are preferable from the viewpoint of ease of synthesis, and a methyl group, a phenyl group, a trifluoro group are preferable.
- a propyl group is more preferred.
- the molecular structure of the component (A) is basically linear or branched (including a straight chain having a branch in a part of the main chain) in which the main chain is composed of repeating diorganosiloxane units.
- a linear diorganopolysiloxane in which both ends of the molecular chain are blocked with a group represented by the general formula (1) is preferable.
- the component (A) may be a single polymer having these molecular structures, a copolymer comprising these molecular structures, or a mixture of two or more of these polymers.
- the viscosity of the organopolysiloxane of component (A) at 25 ° C. is preferably 10 to 100,000 mPa ⁇ s, considering that the workability of the composition and the mechanical properties of the cured product are further improved, and 10 to 50,000 mPa. -S is more preferable.
- This viscosity range usually corresponds to about 10 to 2,000, preferably about 50 to 1,100 in terms of number average degree of polymerization in the case of linear organopolysiloxane.
- the viscosity can be measured with a rotational viscometer (for example, BL type, BH type, BS type, cone plate type, rheometer, etc.) (hereinafter the same).
- the degree of polymerization can be determined, for example, as a number average degree of polymerization (or number average molecular weight) in terms of polystyrene in gel permeation chromatography (GPC) analysis using toluene or the like as a developing solvent (hereinafter referred to as “average molecular weight”). The same).
- (A) component organopolysiloxane examples include, but are not limited to, the following (2) to (4).
- n is a number having the above-mentioned value of the viscosity of the organopolysiloxane, preferably 1 to 800, preferably 50 to 600. More preferred.
- organopolysiloxane can be produced by a known method.
- the organopolysiloxane represented by the above formula (2) includes a dimethylvinylsiloxy group-blocked dimethylsiloxane / diphenylsiloxane copolymer at both ends and 3- (1,1,3,3-tetramethyldisiloxanyl). Obtained as a hydrosilylation reaction product with propyl methacrylate (CAS No. 96474-12-3).
- the organopolysiloxane represented by the above formula (3) is obtained by reacting 2-hydroxyethyl acrylate with a hydrosilylation reaction product of a dimethylvinylsiloxy group-blocked dimethylsiloxane / diphenylsiloxane copolymer and chlorodimethylsilane. Obtainable.
- the organopolysiloxane represented by the above formula (4) is obtained by reacting 2-hydroxyethyl acrylate with a hydrosilylation reaction product of a dimethylvinylsiloxy group-blocked dimethylsiloxane / diphenylsiloxane copolymer and dichloromethylsilane. Obtainable.
- (B) Monofunctional (meth) acrylate compound not containing siloxane structure Specific examples of the monofunctional (meth) acrylate compound (B) not containing siloxane structure include isoamyl acrylate, lauryl acrylate, stearyl acrylate, ethoxy-diethylene glycol acrylate, Examples include methoxy-triethylene glycol acrylate, 2-ethylhexyl-diglycol acrylate, phenoxyethyl acrylate, phenoxydiethylene glycol acrylate, tetrahydrofurfuryl acrylate, and isobornyl acrylate. These may be used alone or in combination of two or more. It may be used. Among these, isobornyl acrylate is particularly preferable.
- polyfunctional (meth) acrylate compound not containing siloxane structure examples include triethylene glycol diacrylate, polytetramethylene glycol diacrylate, neo Examples include pentyl glycol diacrylate, 1,6-hexanediol diacrylate, dimethylol-tricyclodecane diacrylate, trimethylolpropane triacrylate, pentaerythritol tetraacrylate, and the like. These may be used alone or in combination of two or more. May be used. Among these, dimethylol-tricyclodecane diacrylate is particularly preferable.
- the amount of the (meth) acrylate compound as the component (B) and the component (C) is in the range of 1 to 500 parts by mass with respect to 100 parts by mass of the component (A).
- the addition amount of the component (B) and the component (C) is less than 1 part by mass with respect to 100 parts by mass of the component (A)
- the viscosity of the whole composition can be adjusted by increasing the addition amount of (B) component and (C) component
- addition amount exceeds 500 mass parts with respect to 100 mass parts of (A) component when addition amount exceeds 500 mass parts with respect to 100 mass parts of (A) component.
- the hardness of the cured product becomes higher than necessary, and the desired tackiness cannot be obtained.
- the addition amount of the component (B) and the component (C) is preferably 10 to 200 parts by mass with respect to 100 parts by mass of the component (A).
- Organopolysiloxane resin (D) is a component that imparts tackiness to the cured product, and (a) R 4 3 SiO 1/2 unit (wherein R 4 represents 1 to 10 carbon atoms) (B) SiO 4/2 units, and the molar ratio of (a) units to (b) units is in the range of 0.6 to 1.2: 1. Resin.
- Specific examples of the monovalent hydrocarbon group having 1 to 10 carbon atoms for R 4 include those having 1 to 10 carbon atoms among the groups exemplified for R 1 above.
- R 4 monovalent hydrocarbon group as in R 1 , part or all of the hydrogen atoms bonded to the carbon atom may be substituted with the other substituents described above.
- the molar ratio of M units is less than 0.6, the adhesive strength and tackiness of the cured product may be reduced, and if it exceeds 1.2, the adhesive strength of the cured product may be reduced. And holding power may decrease.
- Photopolymerization initiator examples include 2,2-diethoxyacetophenone, 2,2-dimethoxy-1,2-diphenylethane-1-one (manufactured by BASF).
- Irgacure 651) 1-hydroxy-cyclohexyl-phenyl-ketone (Irgacure 184 from BASF), 2-hydroxy-2-methyl-1-phenyl-propan-1-one (Irgacure 1173 from BASF), 2-hydroxy-1- ⁇ 4- [4- (2-Hydroxy-2-methyl-propionyl) -benzyl] -phenyl ⁇ -2-methyl-propan-1-one (Irgacure 127 from BASF), phenylglyoxylic acid methyl ester (from BASF) Irgacure MBF), 2-methyl-1- [4- (methyl E) phenyl] -2-morpholinopropan-1-one (Irgacure 907 from BASF), 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -1-butanone (Irgacure 369 from BASF), Bis (2,4,6-trimethylbenzoyl) -pheny
- the addition amount of the photopolymerization initiator is in the range of 0.1 to 20 parts by mass with respect to 100 parts by mass of (A). When it is less than 0.1 parts by mass, the curability is insufficient, and when it is added in an amount exceeding 20 parts by mass, the deep part curability deteriorates.
- the ultraviolet curable silicone pressure-sensitive adhesive composition of the present invention comprises an organopolysiloxane having one acryloyloxyalkyl group or one methacryloyloxyalkyl group in one molecule, if necessary, in addition to the above essential components. May be included. By including this component in the composition, it is possible to adjust the flexibility and tackiness of the cured product.
- Specific examples of the acryloyloxyalkyl group include an acryloyloxybutyl group and an acryloyloxypropyl group.
- Specific examples of the methacryloyloxyalkyl group include a methacryloyloxybutyl group and a methacryloyloxypropyl group. From the viewpoint of easiness, a methacryloyloxypropyl group or an acryloyloxypropyl group is preferable.
- the organic group bonded to the silicon atom other than the acryloyloxyalkyl group or the methacryloyloxyalkyl group includes, for example, the same groups as those described above for R 1.
- a monovalent hydrocarbon group having 1 to 12 carbon atoms, preferably 1 to 10 carbon atoms excluding the group is preferred. Specific examples thereof include the same groups as those exemplified above for R 1 , but an alkyl group, an aryl group, and a halogenated alkyl group are preferable from the viewpoint of ease of synthesis, and a methyl group, a phenyl group, a trifluoro group are preferable.
- a propyl group is more preferred.
- the viscosity of the organopolysiloxane of component (F) at 25 ° C. is preferably 1 to 100,000 mPa ⁇ s, considering that the workability of the composition and the mechanical properties of the cured product are further improved, and preferably 1 to 10,000 mPa ⁇ s. -S is more preferable.
- This viscosity range usually corresponds to about 5 to 1,000, preferably about 5 to 500 in terms of number average degree of polymerization in the case of linear organopolysiloxane.
- Component acryloyloxyalkyl group or methacryloyloxyalkyl group in the organopolysiloxane molecule may be bonded at the molecular chain end or at the molecular chain non-terminal (that is, in the middle of the molecular chain or in the molecular chain side chain).
- those having one acryloyloxyalkyl group or methacryloyloxyalkyl group at one end of one molecule are preferable.
- component (F) include, but are not limited to, those represented by the following formulas (5) and (6).
- n is a number having the above-mentioned value of the viscosity of the organopolysiloxane, preferably 1 to 200, and more preferably 10 to 100.
- a colorant pigment or dye
- a silane coupling agent an adhesion assistant
- a polymerization inhibitor an antioxidant
- a light-resistant stabilizer are included within the range not impairing the effects of the present invention.
- Additives such as certain UV absorbers and light stabilizers can be blended.
- the composition of the present invention can be used by appropriately mixing with other resin compositions.
- the ultraviolet curable silicone pressure-sensitive adhesive composition of the present invention is obtained by mixing the above components (A) to (E) and, if necessary, the component (F) and other components in any order, stirring, and the like. be able to.
- the apparatus used for operations, such as stirring is not specifically limited, A crusher, 3 rolls, a ball mill, a planetary mixer, etc. can be used. Moreover, you may combine these apparatuses suitably.
- the viscosity of the ultraviolet curable silicone pressure-sensitive adhesive composition of the present invention is not particularly limited, but is preferably 100,000 mPa ⁇ s or less and more preferably 50,000 mPa ⁇ s or less at 23 ° C. from the viewpoint of workability. .
- the lower limit is not particularly limited, but is usually about 100 mPa ⁇ s.
- the pressure-sensitive ultraviolet curable silicone composition of the present invention is rapidly cured by irradiating with ultraviolet rays.
- the ultraviolet light source to be irradiated include a UVLED lamp, a high-pressure mercury lamp, an ultrahigh-pressure mercury lamp, a metal halide lamp, a carbon arc lamp, and a xenon lamp.
- the amount of UV irradiation is preferably 1 to 10,000 mJ / cm 2 , more preferably 10 to 10 mm, for a sheet formed with the composition of the present invention having a thickness of about 2.0 mm. 6,000 mJ / cm 2 .
- the ultraviolet rays when ultraviolet rays having an illuminance of 100 mW / cm 2 are used, the ultraviolet rays may be irradiated for about 0.01 to 100 seconds.
- the adhesive strength of the cured product obtained by ultraviolet irradiation is not particularly limited, but is preferably from 0.01 to 100 MPa in view of the balance between the peelability of the transferred material and the retention property, More preferable is 02 to 50 MPa.
- the ultraviolet curable silicone adhesive composition of this invention can also be utilized as an adhesive article by apply
- plastic film, glass, metal and the like can be used without particular limitation.
- Plastic films include polyethylene film, polypropylene film, polyester film, polyimide film, polyvinyl chloride film, polyvinylidene chloride film, polyvinyl alcohol film, polycarbonate film, polystyrene film, ethylene-vinyl acetate copolymer film, ethylene-vinyl alcohol. Examples thereof include a copolymer film and a triacetyl cellulose film.
- Coating methods include, for example, spin coaters, comma coaters, lip coaters, roll coaters, die coaters, knife coaters, blade coaters, rod coaters, kiss coaters, gravure coaters, screen coating, dip coating, cast coating, and the like.
- the coating method can be appropriately selected and used.
- the ultraviolet curable silicone pressure-sensitive adhesive composition of the present invention is a solvent-free type, potting using a mold is possible as a method for producing a cured product. Bubbles may be involved when pouring into a mold in potting, but the bubbles can be removed by decompression.
- a mold for example, a resist mold in which desired irregularities are formed by a photoresist on a silicon wafer can be used.
- a release agent treatment on the container before pouring the composition.
- fluorine-based or silicone-based ones can be used.
- the ultraviolet curable silicone pressure-sensitive adhesive composition of the present invention is usually used as it is, but in the case where improvement in handling property, coating property to a substrate, etc. is required, the range does not impair the characteristics of the present invention. It is also acceptable to use after diluting with an organic solvent.
- B Component (B-1) Isobornyl acrylate (Kyoeisha Chemical Co., Ltd. Light acrylate IB-XA) (B-2) (Acryloxymethyl) -pentamethyldisiloxane
- C Component (C-2) Dimethylol-tricyclodecane diacrylate (Kyoeisha Chemical Co., Ltd. light acrylate DCP-A)
- D Component (D) Component (D-1) Organopoly having a Me 3 SiO 1/2 unit and a SiO 2 unit and having a (Me 3 SiO 1/2 unit) / (SiO 2 unit) molar ratio of 0.85 60 mass% toluene solution of siloxane resin (number average molecular weight 3,500)
- E component
- F component
- Examples 1 to 4 and Comparative Examples 1 to 3 The components (A) to (F) were mixed in the composition shown in Table 1, and toluene was distilled off at 100 ° C. under reduced pressure to prepare each silicone composition shown in Table 1.
- the viscosity of the composition in Table 1 is a value measured at 23 ° C. using a rotational viscometer.
- the prepared silicone composition was irradiated with ultraviolet light having a wavelength of 365 nm at room temperature (25 ° C.) in a nitrogen atmosphere using an eye UV electronic control device (model UBX0601-01) manufactured by Igraphic Co., Ltd. It was cured by irradiating with ultraviolet rays so as to be 000 mJ / cm 2 .
- the hardness of the cured product was measured according to Japan Rubber Association standard SRIS0101.
- the tackiness of the cured product was measured with a small desktop tester EZ-SX manufactured by Shimadzu Corporation. Specifically, it is a value obtained by measuring a load applied when a 1 mm square SUS probe was pressed at 1 MPa for 15 seconds on a 1 mm thick cured product and then pulled at a speed of 200 mm / min. Moreover, the presence or absence of cohesive failure on the surface of the test specimen was also evaluated visually. The results are also shown in Table 1.
- the ultraviolet curable silicone pressure-sensitive adhesive compositions prepared in Examples 1 to 4 have good workability and curability, and the cured product has excellent adhesiveness. Since it does not cause cohesive failure, it has excellent strength and is useful as a temporary fixing material for transporting micro objects such as elements.
- the comparative example 1 which does not contain (B) component and (C) component, it turns out that a composition becomes very high viscosity and workability
- operativity is bad.
- the comparative example 2 with which there are too many compounding quantities of (D) component outside the range of this invention it turns out that a composition solidifies and it becomes difficult to handle.
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Abstract
Description
この技術は、マイクロ・トランスファー・プリンティング技術と呼ばれ、エラストマーの粘着力で微細な部品を一偏にピックアップし、より粘着力の強い所望の場所に移送させるという技術である。
しかしながら、加熱硬化型のシリコーン系粘着剤を用いた場合、加熱工程が必須であるためエネルギーを必要とし、また、材料の加熱および冷却に多くの時間を要する。
したがって、上記特許文献4の材料では持ち上げられないような素子や部品にも適用可能な、より強力な粘着力を有する紫外線硬化性粘着シリコーン材料が望まれている。
1. (A)下記一般式(1)
で示される基を1分子中に2個有するオルガノポリシロキサン:100質量部、
(B)シロキサン構造を含まない単官能(メタ)アクリレート化合物および(C)シロキサン構造を含まない多官能(メタ)アクリレート化合物のいずれか一方または双方:1~500質量部、
(D)(a)R4 3SiO1/2単位(式中、R4は、炭素原子数1~10の一価炭化水素基を表す。)と(b)SiO4/2単位からなり、(a)単位と(b)単位とのモル比が0.6~1.2:1の範囲にあるオルガノポリシロキサンレジン:1~5,000質量部、並びに
(E)光重合開始剤:0.01~20質量部
を含有してなることを特徴とする紫外線硬化型シリコーン粘着剤組成物、
2. 更に、(F)アクリロイルオキシアルキル基またはメタクリロイルオキシアルキル基を1分子中に1個有するオルガノポリシロキサンを、(A)成分100質量部に対して0.1~1,000質量部含む1の紫外線硬化型シリコーン粘着剤組成物、
3. 23℃での粘度が100,000mPa・s以下である1または2の紫外線硬化型シリコーン粘着剤組成物、
4. 1~3のいずれかの紫外線硬化型シリコーン粘着剤組成物の硬化物、
5. 4の硬化物からなる粘着剤
を提供する。
本発明に係る紫外線硬化型シリコーン粘着剤組成物は、(A)下記一般式(1)で示される基を1分子中に2個有するオルガノポリシロキサン:100質量部、
(B)シロキサン構造を含まない単官能(メタ)アクリレート化合物および(C)シロキサン構造を含まない多官能(メタ)アクリレート化合物のいずれか一方または双方:1~500質量部、
(D)(a)R4 3SiO1/2単位(式中、R4は、炭素原子数1~10の非置換もしくは置換の一価炭化水素基を表す。)と(b)SiO4/2単位からなり、(a)単位と(b)単位とのモル比が0.6~1.2:1の範囲にあるオルガノポリシロキサンレジン:1~5000質量部、並びに
(E)光重合開始剤:0.01~20質量部
を含有してなることを特徴とする。
本発明に使用される(A)成分は、本組成物の架橋成分であり、下記一般式(1)で示される基を1分子中に2個有し、主鎖が実質的にジオルガノシロキサン単位の繰返しからなるオルガノポリシロキサンである。
また、これら一価炭化水素基の炭素原子に結合した水素原子の一部または全部は、その他の置換基で置換されていてもよく、その具体例としては、クロロメチル、ブロモエチル、トリフルオロプロピル、シアノエチル基等のハロゲン置換炭化水素基や、シアノ置換炭化水素基などが挙げられる。
これらの中でも、R1としては、炭素原子数1~5のアルキル基、フェニル基が好ましく、メチル基、エチル基、フェニル基がより好ましい。
これらの中でも、R2としては、酸素原子、メチレン、エチレン、プロピレン基が好ましく、酸素原子またはエチレン基がより好ましい。
R3の具体例としては、下記式で示されるものが挙げられるが、これらに限定されるものではない。
これらの具体例としては、上記R1で例示した基と同様のものが挙げられるが、合成の簡便さから、アルキル基、アリール基、ハロゲン化アルキル基が好ましく、メチル基、フェニル基、トリフロロプロピル基がより好ましい。
(A)成分は、これらの分子構造を有する単一の重合体、これらの分子構造からなる共重合体、またはこれらの重合体の2種以上の混合物であってもよい。
本発明において、重合度(または分子量)は、例えば、トルエン等を展開溶媒として、ゲルパーミエーションクロマトグラフィ(GPC)分析におけるポリスチレン換算の数平均重合度(または数平均分子量)として求めることができる(以下、同様)。
上記式(3)で表されるオルガノポリシロキサンは、両末端ジメチルビニルシロキシ基封鎖ジメチルシロキサン・ジフェニルシロキサン共重合体とクロロジメチルシランとのヒドロシリル化反応物に、2-ヒドロキシエチルアクリレートを反応させて得ることができる。
上記式(4)で表されるオルガノポリシロキサンは、両末端ジメチルビニルシロキシ基封鎖ジメチルシロキサン・ジフェニルシロキサン共重合体とジクロロメチルシランとのヒドロシリル化反応物に、2-ヒドロキシエチルアクリレートを反応させて得ることができる。
シロキサン構造を含まない単官能(メタ)アクリレート化合物(B)の具体例としては、イソアミルアクリレート、ラウリルアクリレート、ステアリルアクリレート、エトキシ-ジエチレングリコールアクリレート、メトキシ-トリエチレングリコールアクリレート、2-エチルヘキシル-ジグリコールアクリレート、フェノキシエチルアクリレート、フェノキシジエチレングリコールアクリレート、テトラヒドロフルフリルアクリレート、イソボルニルアクリレート等が挙げられ、これらは単独で用いても2種以上混合して用いてもよい。
これらの中でも、特にイソボルニルアクリレートが好ましい。
シロキサン構造を含まない多官能(メタ)アクリレート化合物(C)の具体例としては、トリエチレングリコールジアクリレート、ポリテトラメチレングリコールジアクリレート、ネオペンチルグリコールジアクリレート、1,6-ヘキサンジオールジアクリレート、ジメチロール-トリシクロデカンジアクリレート、トリメチロールプロパントリアクリレート、ペンタエリスリトールテトラアクリレート等が挙げられ、これらは単独で用いても、2種以上混合して用いてもよい。
これらの中でも、特にジメチロール-トリシクロデカンジアクリレートが好ましい。
特に、(B)成分および(C)成分の添加量は、(A)成分100質量部に対し、10~200質量部が好ましい。
(D)成分は、硬化物に粘着性を付与する成分であり、(a)R4 3SiO1/2単位(式中、R4は、炭素原子数1~10の一価炭化水素基である)と(b)SiO4/2単位からなり、(a)単位と(b)単位のモル比が0.6~1.2:1の範囲にあるオルガノポリシロキサンレジンである。
R4における炭素原子数1~10の一価炭化水素基の具体例としては、上記R1で例示した基のうち、炭素原子数1~10のものが挙げられるが、中でもメチル、エチル、n-プロピル、n-ブチル基等の炭素原子数2~6のアルキル基;フェニル、トリル基等の炭素原子数6~10のアリール基、ベンジル基等の炭素原子数7~10のアラルキル基;ビニル基、アリル基、ブテニル基等の炭素原子数2~6のアルケニル基等が好ましい。
なお、上記R4の一価炭化水素基も、R1と同様に、炭素原子に結合した水素原子の一部または全部が、上述したその他の置換基で置換されていてもよい。
硬化物の粘着力、保持力およびタック性をより適切な範囲とすることを考慮すると、M単位とQ単位のモル比は、M単位:Q単位=0.7~1.2:1が好ましい。
本発明で使用可能な光重合開始剤の具体例としては、2,2-ジエトキシアセトフェノン、2,2-ジメトキシ-1,2-ジフェニルエタン-1-オン(BASF製Irgacure 651)、1-ヒドロキシ-シクロヘキシル-フェニル-ケトン(BASF製Irgacure 184)、2-ヒドロキシ-2-メチル-1-フェニル-プロパン-1-オン(BASF製Irgacure 1173)、2-ヒドロキシ-1-{4-[4-(2-ヒドロキシ-2-メチル-プロピオニル)-ベンジル]-フェニル}-2-メチル-プロパン-1-オン(BASF製Irgacure 127)、フェニルグリオキシリックアシッドメチルエステル(BASF製Irgacure MBF)、2-メチル-1-[4-(メチルチオ)フェニル]-2-モルフォリノプロパン-1-オン(BASF製Irgacure 907)、2-ベンジル-2-ジメチルアミノ-1-(4-モルフォリノフェニル)-1-ブタノン(BASF製Irgacure 369)、ビス(2,4,6-トリメチルベンゾイル)-フェニルフォスフィンオキサイド(BASF製Irgacure 819)、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(BASF製Irgacure TPO)等が挙げられ、これらは単独で用いても、2種以上組み合わせて用いてもよい。
これらの中でも、(A)成分との相溶性の観点から、2,2-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(BASF製Irgacure 1173)、ビス(2,4,6-トリメチルベンゾイル)-フェニルフォスフィンオキサイド(BASF製Irgacure 819)、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(BASF製Irgacure TPO)が好ましい。
本発明の紫外線硬化型シリコーン粘着剤組成物は、上記必須成分以外に、必要により、アクリロイルオキシアルキル基、またはメタクリロイルオキシアルキル基を1分子中に1個有するオルガノポリシロキサンを含んでもよい。本成分を組成物中に含有させることで、その硬化物の柔軟性や粘着性を調節することが可能である。
アクリロイルオキシアルキル基の具体例としては、アクリロイルオキシブチル基、アクリロイルオキシプロピル基が挙げられ、メタクリロイルオキシアルキル基の具体例としては、メタクリロイルオキシブチル基、メタクリロイルオキシプロピル基等が挙げられるが、合成のし易さから、メタクリロイルオキシプロピル基またはアクリロイルオキシプロピル基が好ましい。
これらの具体例としては、上記R1で例示した基と同様のものが挙げられるが、合成の簡便さから、アルキル基、アリール基、ハロゲン化アルキル基が好ましく、メチル基、フェニル基、トリフロロプロピル基がより好ましい。
また、本発明の組成物はその他の樹脂組成物と適宜混合して使用することもできる。
この場合、照射する紫外線の光源としては、例えば、UVLEDランプ、高圧水銀灯、超高圧水銀灯、メタルハライドランプ、カーボンアークランプ、キセノンランプ等が挙げられる。
紫外線の照射量(積算光量)は、例えば、本発明の組成物を2.0mm程度の厚みに成形したシートに対して、好ましくは1~10,000mJ/cm2であり、より好ましくは10~6,000mJ/cm2である。すなわち、照度100mW/cm2の紫外線を用いた場合、0.01~100秒程度紫外線を照射すればよい。
本発明において、紫外線照射によって得られた硬化物の粘着力は、特に限定されるものではないが、移送物の剥離性と保持性とのバランスを考慮すると、0.01~100MPaが好ましく、0.02~50MPaがより好ましい。
基材としては、プラスチックフィルム、ガラス、金属等、特に制限なく使用できる。
プラスチックフィルムとしては、ポリエチレンフィルム、ポリプロピレンフィルム、ポリエステルフィルム、ポリイミドフィルム、ポリ塩化ビニルフィルム、ポリ塩化ビニリデンフィルム、ポリビニルアルコールフィルム、ポリカーボネートフィルム、ポリスチレンフィルム、エチレン-酢酸ビニル共重合体フィルム、エチレン-ビニルアルコール共重合体フィルム、トリアセチルセルロースフィルム等が挙げられる。
ガラスについても、厚みや種類などについて特に制限はなく、化学強化処理などをしたものでもよい。
なお、基材と粘着剤層の密着性を向上させるために、基材に予めプライマー処理、プラズマ処理等を施したものを用いてもよい。
ポッティングにおける型へ流し込む際に気泡を巻き込むことがあるが、減圧により脱泡することができる。型としては、例えば、シリコンウエハー上にフォトレジストにより所望の凹凸をつけたレジスト型を用いることができる。
硬化後、型から硬化物を取り出したい場合には、組成物を流し込む前に容器に離型剤処理を施す方が好ましい。離型剤としてはフッ素系、シリコーン系等のものが使用可能である。
なお、実施例で使用した各成分の化合物は以下のとおりである。
(A)成分
(B-1)
イソボルニルアクリレート(共栄社化学(株)製ライトアクリレートIB-XA)
(B-2)
(アクリロキシメチル)-ペンタメチルジシロキサン
(C-2)
ジメチロール-トリシクロデカンジアクリレート(共栄社化学(株)製ライトアクリレートDCP-A)
(D)成分
(D-1)Me3SiO1/2単位およびSiO2単位を含有し、(Me3SiO1/2単位)/(SiO2単位)のモル比が0.85であるオルガノポリシロキサンレジン(数平均分子量3,500)の60質量%トルエン溶液
(E)成分
(E-1)2-ヒドロキシ-2-メチル-1-フェニル-プロパン-1-オン(BASFジャパン(株)製Irgacure 1173)
(F)成分
上記(A)~(F)成分を表1の組成で混合し、減圧下にて100℃でトルエンを留去し、表1記載の各シリコーン組成物を調製した。なお、表1における組成物の粘度は回転粘度計を用いて23℃で測定した値である。
調製したシリコーン組成物を、アイグラフィック(株)製アイUV電子制御装置(型式UBX0601-01)を用い、窒素雰囲気下、室温(25℃)で、波長365nmの紫外光での照射量が4,000mJ/cm2となるように紫外線を照射し、硬化させた。硬化物の硬度は日本ゴム協会標準規格SRIS0101に準じて測定した。
硬化物の粘着性は、(株)島津製作所製小型卓上試験機EZ-SXにより測定した。具体的には、1mm厚の硬化物に1mm角SUS製プローブを1MPaで15秒間押し付けた後、200mm/minの速度で引っ張った際にかかる負荷を測定した値である。また、目視にて試験体の表面の凝集破壊の有無についても評価した。それらの結果を併せて表1に示す。
一方、(B)成分および(C)成分を含まない比較例1では、組成物が極めて高粘度となり、作業性が悪いことがわかる。
また、(D)成分の配合量が本発明の範囲を外れて多すぎる比較例2では、組成物が固形化して取り扱いが困難となることがわかる。
さらに、(B)成分にシロキサン構造を含む単官能アクリレート化合物を用いた比較例3では、粘着性は高いが、粘着性試験で凝集破壊を起こし、硬化物の強度が不十分であることがわかる。
Claims (5)
- (A)下記一般式(1)
で示される基を1分子中に2個有するオルガノポリシロキサン:100質量部、
(B)シロキサン構造を含まない単官能(メタ)アクリレート化合物および(C)シロキサン構造を含まない多官能(メタ)アクリレート化合物のいずれか一方または双方:1~500質量部、
(D)(a)R4 3SiO1/2単位(式中、R4は、炭素原子数1~10の一価炭化水素基を表す。)と(b)SiO4/2単位からなり、(a)単位と(b)単位とのモル比が0.6~1.2:1の範囲にあるオルガノポリシロキサンレジン:1~5,000質量部、並びに
(E)光重合開始剤:0.01~20質量部
を含有してなることを特徴とする紫外線硬化型シリコーン粘着剤組成物。 - 更に、(F)アクリロイルオキシアルキル基またはメタクリロイルオキシアルキル基を1分子中に1個有するオルガノポリシロキサンを、(A)成分100質量部に対して0.1~1,000質量部含む請求項1記載の紫外線硬化型シリコーン粘着剤組成物。
- 23℃での粘度が100,000mPa・s以下である請求項1または2記載の紫外線硬化型シリコーン粘着剤組成物。
- 請求項1~3のいずれか1項記載の紫外線硬化型シリコーン粘着剤組成物の硬化物。
- 請求項4記載の硬化物からなる粘着剤。
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Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5234064B2 (ja) | 1973-12-18 | 1977-09-01 | ||
JPS5825738B2 (ja) | 1974-01-23 | 1983-05-30 | ウエスチングハウス エレクトリック コ−ポレ−ション | 真空蒸着用マスク |
JPH03139512A (ja) * | 1989-09-22 | 1991-06-13 | Minnesota Mining & Mfg Co <3M> | ヒドロシル化アズラクトン官能性ケイ素含有化合物及びその誘導体 |
JP2631098B2 (ja) | 1995-10-09 | 1997-07-16 | 東レ・ダウコーニング・シリコーン株式会社 | シリコーン感圧接着剤組成物 |
WO2001005846A1 (en) * | 1999-07-19 | 2001-01-25 | Loctite Corporation | Resin-reinforced uv, moisture and uv/moisture dual curable silicone compositions |
US20030064232A1 (en) * | 2001-08-16 | 2003-04-03 | John Allen | Siloxane-containing compositions curable by radiation to silicone elastomers |
CN104610696A (zh) * | 2015-01-05 | 2015-05-13 | 烟台德邦先进硅材料有限公司 | 一种用于uv固化的有机硅组合物 |
JP5989417B2 (ja) | 2012-06-20 | 2016-09-07 | モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 | 紫外線硬化型シリコーン樹脂組成物、及びそれを用いた画像表示装置 |
KR20160129219A (ko) * | 2015-04-29 | 2016-11-09 | 삼성에스디아이 주식회사 | 실리콘 점착제 조성물, 이로부터 형성된 실리콘 점착 필름 및 이를 포함하는 광학표시장치 |
JP2016190979A (ja) * | 2015-03-31 | 2016-11-10 | 信越化学工業株式会社 | 画像表示装置用紫外線硬化型液状オルガノポリシロキサン組成物、該組成物を含む画像表示装置用接着剤、該接着剤を用いた画像表示装置及び該接着剤を用いた接着方法 |
CN106497505A (zh) * | 2016-09-21 | 2017-03-15 | 矽时代材料科技股份有限公司 | 一种可重工贴合用的紫外光固化液体光学硅胶及其制备方法和应用 |
WO2017048890A1 (en) * | 2015-09-18 | 2017-03-23 | Henkel IP & Holding GmbH | Curable and optically clear pressure sensitive adhesives and uses thereof |
WO2017068762A1 (en) * | 2015-10-19 | 2017-04-27 | Dow Corning Toray Co., Ltd. | Active energy ray curable hot melt silicone composition, cured product thereof, and method of producing film |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5234064U (ja) | 1975-09-01 | 1977-03-10 | ||
JPS5825738U (ja) | 1981-08-14 | 1983-02-18 | 三菱自動車工業株式会社 | 自動車の後部座席 |
US5147957A (en) | 1989-09-22 | 1992-09-15 | Minnesota Mining And Manufacturing Company | Hydrosilated azlactone functional silicon containing compounds and derivatives thereof |
EP0576544B1 (en) * | 1991-03-20 | 1997-06-04 | Minnesota Mining And Manufacturing Company | Radiation-curable acrylate/silicone pressure-sensitive adhesive compositions |
JP5234064B2 (ja) | 2010-08-23 | 2013-07-10 | 信越化学工業株式会社 | 無溶剤型付加型シリコーン粘着剤組成物及び粘着性物品 |
WO2012091742A1 (en) * | 2010-12-29 | 2012-07-05 | 3M Innovative Properties Company | Low adhesion backsize for silicone adhesive articles and methods |
JP5825738B2 (ja) | 2011-12-29 | 2015-12-02 | 東レ・ダウコーニング株式会社 | シリコーン系感圧接着剤組成物、積層体およびシリコーン粘着テープ |
JP6064937B2 (ja) * | 2014-03-31 | 2017-01-25 | 信越化学工業株式会社 | 粘着剤組成物、粘着偏光板及び液晶表示装置 |
CN106188384B (zh) * | 2016-07-29 | 2018-08-28 | 安徽优科新材料科技有限公司 | 一种无苯型的高光泽高固含丙烯酸树脂及其制备方法 |
WO2018048890A1 (en) * | 2016-09-06 | 2018-03-15 | Solarreserve Technology, Llc | Heliostat mirror panels with pivotable hardware modules |
WO2019065398A1 (ja) * | 2017-09-29 | 2019-04-04 | 信越化学工業株式会社 | 紫外線硬化型シリコーン粘着剤組成物およびその硬化物 |
-
2018
- 2018-05-07 US US16/619,850 patent/US11124680B2/en active Active
- 2018-05-07 EP EP18813290.6A patent/EP3636723A4/en active Pending
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- 2018-05-07 WO PCT/JP2018/017581 patent/WO2018225430A1/ja unknown
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- 2018-05-07 JP JP2019523403A patent/JP6927298B2/ja active Active
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Patent Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5234064B2 (ja) | 1973-12-18 | 1977-09-01 | ||
JPS5825738B2 (ja) | 1974-01-23 | 1983-05-30 | ウエスチングハウス エレクトリック コ−ポレ−ション | 真空蒸着用マスク |
JPH03139512A (ja) * | 1989-09-22 | 1991-06-13 | Minnesota Mining & Mfg Co <3M> | ヒドロシル化アズラクトン官能性ケイ素含有化合物及びその誘導体 |
JP2631098B2 (ja) | 1995-10-09 | 1997-07-16 | 東レ・ダウコーニング・シリコーン株式会社 | シリコーン感圧接着剤組成物 |
WO2001005846A1 (en) * | 1999-07-19 | 2001-01-25 | Loctite Corporation | Resin-reinforced uv, moisture and uv/moisture dual curable silicone compositions |
US20030064232A1 (en) * | 2001-08-16 | 2003-04-03 | John Allen | Siloxane-containing compositions curable by radiation to silicone elastomers |
JP5989417B2 (ja) | 2012-06-20 | 2016-09-07 | モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 | 紫外線硬化型シリコーン樹脂組成物、及びそれを用いた画像表示装置 |
CN104610696A (zh) * | 2015-01-05 | 2015-05-13 | 烟台德邦先进硅材料有限公司 | 一种用于uv固化的有机硅组合物 |
JP2016190979A (ja) * | 2015-03-31 | 2016-11-10 | 信越化学工業株式会社 | 画像表示装置用紫外線硬化型液状オルガノポリシロキサン組成物、該組成物を含む画像表示装置用接着剤、該接着剤を用いた画像表示装置及び該接着剤を用いた接着方法 |
KR20160129219A (ko) * | 2015-04-29 | 2016-11-09 | 삼성에스디아이 주식회사 | 실리콘 점착제 조성물, 이로부터 형성된 실리콘 점착 필름 및 이를 포함하는 광학표시장치 |
WO2017048890A1 (en) * | 2015-09-18 | 2017-03-23 | Henkel IP & Holding GmbH | Curable and optically clear pressure sensitive adhesives and uses thereof |
WO2017068762A1 (en) * | 2015-10-19 | 2017-04-27 | Dow Corning Toray Co., Ltd. | Active energy ray curable hot melt silicone composition, cured product thereof, and method of producing film |
CN106497505A (zh) * | 2016-09-21 | 2017-03-15 | 矽时代材料科技股份有限公司 | 一种可重工贴合用的紫外光固化液体光学硅胶及其制备方法和应用 |
Non-Patent Citations (3)
Title |
---|
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 96474-12-3 |
JOHN A. ROGERS: "Nature Materials", vol. 6, 11 December 2005, NATURE PUBLISHING GROUP, article "Transfer printing by kinetic control of adhesion to an elastomeric stamp", pages: 33 - 38 |
See also references of EP3636723A4 |
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JPWO2018225430A1 (ja) | 2020-04-02 |
KR20200015594A (ko) | 2020-02-12 |
EP3636723A1 (en) | 2020-04-15 |
KR102542235B1 (ko) | 2023-06-12 |
TWI773759B (zh) | 2022-08-11 |
CN110709488B (zh) | 2022-01-14 |
US20200131408A1 (en) | 2020-04-30 |
CN110709488A (zh) | 2020-01-17 |
JP6927298B2 (ja) | 2021-08-25 |
TW201906955A (zh) | 2019-02-16 |
US11124680B2 (en) | 2021-09-21 |
EP3636723A4 (en) | 2021-04-14 |
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