WO2022203042A1 - 紫外線硬化性組成物及びその用途 - Google Patents
紫外線硬化性組成物及びその用途 Download PDFInfo
- Publication number
- WO2022203042A1 WO2022203042A1 PCT/JP2022/014393 JP2022014393W WO2022203042A1 WO 2022203042 A1 WO2022203042 A1 WO 2022203042A1 JP 2022014393 W JP2022014393 W JP 2022014393W WO 2022203042 A1 WO2022203042 A1 WO 2022203042A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- component
- group
- groups
- ultraviolet
- formula
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 324
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 230
- 125000000524 functional group Chemical group 0.000 claims abstract description 201
- 150000001875 compounds Chemical class 0.000 claims abstract description 165
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 59
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 36
- 150000001282 organosilanes Chemical class 0.000 claims abstract description 34
- 238000002834 transmittance Methods 0.000 claims abstract description 31
- 239000000758 substrate Substances 0.000 claims abstract description 26
- -1 cyclic organosilanes Chemical class 0.000 claims description 233
- 125000003342 alkenyl group Chemical group 0.000 claims description 78
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 69
- 125000003700 epoxy group Chemical group 0.000 claims description 32
- 125000004122 cyclic group Chemical group 0.000 claims description 25
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 239000011248 coating agent Substances 0.000 claims description 18
- 239000010410 layer Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 238000010521 absorption reaction Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 11
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 10
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 9
- 239000011247 coating layer Substances 0.000 claims description 8
- 125000003566 oxetanyl group Chemical group 0.000 claims description 8
- MZAQJZCJMSDKJP-UHFFFAOYSA-N trimethyl-[methyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]-trimethylsilyloxysilyl]oxysilane Chemical compound C1C(CC[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C)CCC2OC21 MZAQJZCJMSDKJP-UHFFFAOYSA-N 0.000 claims description 7
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 6
- 229910004283 SiO 4 Inorganic materials 0.000 claims description 6
- UQOXIKVRXYCUMT-UHFFFAOYSA-N [dimethyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silyl]oxy-dimethyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1CC2OC2CC1CC[Si](C)(C)O[Si](C)(C)CCC1CC2OC2CC1 UQOXIKVRXYCUMT-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- AINIIHKVQLDWBC-UHFFFAOYSA-N C[SiH2]O[SiH](C)C(CCC1CC2OC2CC1)(CCC1CC2OC2CC1)CCC1CC2OC2CC1 Chemical compound C[SiH2]O[SiH](C)C(CCC1CC2OC2CC1)(CCC1CC2OC2CC1)CCC1CC2OC2CC1 AINIIHKVQLDWBC-UHFFFAOYSA-N 0.000 claims description 5
- LZOFCSIVPONNAC-UHFFFAOYSA-N bis[[[dimethyl-[2-(7-oxabicyclo[4.1.0]heptan-3-yl)ethyl]silyl]oxy-dimethylsilyl]oxy]-dimethylsilane Chemical compound C[Si](C)(CCC1CCC2OC2C1)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)CCC1CCC2OC2C1 LZOFCSIVPONNAC-UHFFFAOYSA-N 0.000 claims description 5
- HDARIBFEXDXGFF-UHFFFAOYSA-N bis[[dimethyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silyl]oxy]-dimethylsilane Chemical compound C1CC2OC2CC1CC[Si](C)(C)O[Si](C)(C)O[Si](C)(C)CCC1CC2OC2CC1 HDARIBFEXDXGFF-UHFFFAOYSA-N 0.000 claims description 5
- QPUYBEKIHDOPRG-UHFFFAOYSA-N bis[[dimethyl-[3-(oxiran-2-ylmethoxy)propyl]silyl]oxy]-dimethylsilane Chemical compound C1OC1COCCC[Si](C)(C)O[Si](C)(C)O[Si](C)(C)CCCOCC1CO1 QPUYBEKIHDOPRG-UHFFFAOYSA-N 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- RPENLVPZIIFBIN-UHFFFAOYSA-N tetrakis[dimethyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silyl] silicate Chemical compound C1CC2OC2CC1CC[Si](C)(C)O[Si](O[Si](C)(C)CCC1CC2OC2CC1)(O[Si](C)(C)CCC1CC2OC2CC1)O[Si](C)(C)CCC1CC2OC2CC1 RPENLVPZIIFBIN-UHFFFAOYSA-N 0.000 claims description 5
- DWUJGFHUOHDVAW-UHFFFAOYSA-N tetrakis[dimethyl-[3-(oxiran-2-ylmethoxy)propyl]silyl] silicate Chemical compound C1OC1COCCC[Si](C)(C)O[Si](O[Si](C)(C)CCCOCC1OC1)(O[Si](C)(C)CCCOCC1OC1)O[Si](C)(C)CCCOCC1CO1 DWUJGFHUOHDVAW-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 55
- 239000003505 polymerization initiator Substances 0.000 description 23
- 229920001577 copolymer Polymers 0.000 description 21
- 238000001723 curing Methods 0.000 description 20
- 125000002091 cationic group Chemical group 0.000 description 16
- 239000000463 material Substances 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 13
- 125000000753 cycloalkyl group Chemical group 0.000 description 13
- 125000003710 aryl alkyl group Chemical group 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 239000003999 initiator Substances 0.000 description 12
- 238000010894 electron beam technology Methods 0.000 description 10
- 125000000962 organic group Chemical group 0.000 description 10
- 238000007641 inkjet printing Methods 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000000654 additive Substances 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 239000004205 dimethyl polysiloxane Substances 0.000 description 8
- 239000002736 nonionic surfactant Substances 0.000 description 8
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 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 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 125000006038 hexenyl group Chemical group 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
- 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 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 238000004382 potting Methods 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 239000002318 adhesion promoter Substances 0.000 description 5
- 150000002894 organic compounds Chemical group 0.000 description 5
- 239000003504 photosensitizing agent Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920002545 silicone oil Polymers 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000007348 radical reaction Methods 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
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 3
- LMKAKZZMFVZRBP-UHFFFAOYSA-N C(C1CO1)OCCC[Si](O[Si](O[Si](O[Si](O[Si](CCCOCC1CO1)(C)C)(C)C)(C)C)(C)C)(C)C Chemical compound C(C1CO1)OCCC[Si](O[Si](O[Si](O[Si](O[Si](CCCOCC1CO1)(C)C)(C)C)(C)C)(C)C)(C)C LMKAKZZMFVZRBP-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- LFKLPJRVSHJZPL-UHFFFAOYSA-N 1,2:7,8-diepoxyoctane Chemical compound C1OC1CCCCC1CO1 LFKLPJRVSHJZPL-UHFFFAOYSA-N 0.000 description 2
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 2
- UZUNCLSDTUBVCN-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-6-(2-phenylpropan-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound C=1C(C(C)(C)CC(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C(O)C=1C(C)(C)C1=CC=CC=C1 UZUNCLSDTUBVCN-UHFFFAOYSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-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
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 2
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 2
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229920002799 BoPET Polymers 0.000 description 2
- XNVLFLJZLMOTQZ-UHFFFAOYSA-N C[SiH2]O[SiH](C)C(CCCOCC1OC1)(CCCOCC1OC1)CCCOCC1OC1 Chemical compound C[SiH2]O[SiH](C)C(CCCOCC1OC1)(CCCOCC1OC1)CCCOCC1OC1 XNVLFLJZLMOTQZ-UHFFFAOYSA-N 0.000 description 2
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 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 2
- 239000007983 Tris buffer Substances 0.000 description 2
- MFIBZDZRPYQXOM-UHFFFAOYSA-N [dimethyl-[3-(oxiran-2-ylmethoxy)propyl]silyl]oxy-dimethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound C1OC1COCCC[Si](C)(C)O[Si](C)(C)CCCOCC1CO1 MFIBZDZRPYQXOM-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001454 anthracenes Chemical class 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- JJRDHFIVAPVZJN-UHFFFAOYSA-N cyclotrisiloxane Chemical compound O1[SiH2]O[SiH2]O[SiH2]1 JJRDHFIVAPVZJN-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000011810 insulating material Substances 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- UJRDRFZCRQNLJM-UHFFFAOYSA-N methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=CC=CC3=N2)=C1O UJRDRFZCRQNLJM-UHFFFAOYSA-N 0.000 description 2
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 2
- 125000005375 organosiloxane group Chemical group 0.000 description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 2
- 125000005372 silanol group Chemical group 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000003595 spectral effect Effects 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
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical compound [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 0.000 description 2
- LWHOMMCIJIJIGV-UHFFFAOYSA-N (1,3-dioxobenzo[de]isoquinolin-2-yl) trifluoromethanesulfonate Chemical compound C1=CC(C(N(OS(=O)(=O)C(F)(F)F)C2=O)=O)=C3C2=CC=CC3=C1 LWHOMMCIJIJIGV-UHFFFAOYSA-N 0.000 description 1
- YPINLRNGSGGJJT-JXMROGBWSA-N (2e)-2-hydroxyimino-1-phenylpropan-1-one Chemical compound O\N=C(/C)C(=O)C1=CC=CC=C1 YPINLRNGSGGJJT-JXMROGBWSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- NPENBPVOAXERED-UHFFFAOYSA-N (4-benzoylphenyl)-phenylmethanone Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 NPENBPVOAXERED-UHFFFAOYSA-N 0.000 description 1
- RLAWXWSZTKMPQQ-UHFFFAOYSA-M (4-tert-butylphenyl)-diphenylsulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(C(C)(C)C)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 RLAWXWSZTKMPQQ-UHFFFAOYSA-M 0.000 description 1
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical class [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 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
- 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
- QWOVEJBDMKHZQK-UHFFFAOYSA-N 1,3,5-tris(3-trimethoxysilylpropyl)-1,3,5-triazinane-2,4,6-trione Chemical compound CO[Si](OC)(OC)CCCN1C(=O)N(CCC[Si](OC)(OC)OC)C(=O)N(CCC[Si](OC)(OC)OC)C1=O QWOVEJBDMKHZQK-UHFFFAOYSA-N 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- FODCFYIWOJIZQL-UHFFFAOYSA-N 1-methylsulfanyl-3,5-bis(trifluoromethyl)benzene Chemical compound CSC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 FODCFYIWOJIZQL-UHFFFAOYSA-N 0.000 description 1
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 1
- WXNYWTHOSFSFDY-UHFFFAOYSA-N 2,2,4,4,6,6,8-heptamethyl-8-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound O1[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si]1(C)CCC1CC2OC2CC1 WXNYWTHOSFSFDY-UHFFFAOYSA-N 0.000 description 1
- IPXMMBFOSWEGRL-UHFFFAOYSA-N 2,2,4,4,6,6,8-heptamethyl-8-[3-(oxiran-2-ylmethoxy)propyl]-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound O1[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si]1(C)CCCOCC1OC1 IPXMMBFOSWEGRL-UHFFFAOYSA-N 0.000 description 1
- WASCPAFRPRXLMA-UHFFFAOYSA-N 2,2,4,4,6-pentamethyl-6-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]-1,3,5,2,4,6-trioxatrisilinane Chemical compound O1[Si](C)(C)O[Si](C)(C)O[Si]1(C)CCC1CC2OC2CC1 WASCPAFRPRXLMA-UHFFFAOYSA-N 0.000 description 1
- OQBZXAHYFBVSIH-UHFFFAOYSA-N 2,2,4,4,6-pentamethyl-6-[3-(oxiran-2-ylmethoxy)propyl]-1,3,5,2,4,6-trioxatrisilinane Chemical compound C[Si]1(O[Si](O[Si](O1)(C)CCCOCC2CO2)(C)C)C OQBZXAHYFBVSIH-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 1
- ZBXBDQPVXIIXJS-UHFFFAOYSA-N 2,4,6,8,10-pentakis(ethenyl)-2,4,6,8,10-pentamethyl-1,3,5,7,9,2,4,6,8,10-pentaoxapentasilecane Chemical compound C=C[Si]1(C)O[Si](C)(C=C)O[Si](C)(C=C)O[Si](C)(C=C)O[Si](C)(C=C)O1 ZBXBDQPVXIIXJS-UHFFFAOYSA-N 0.000 description 1
- VMAWODUEPLAHOE-UHFFFAOYSA-N 2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound C=C[Si]1(C)O[Si](C)(C=C)O[Si](C)(C=C)O[Si](C)(C=C)O1 VMAWODUEPLAHOE-UHFFFAOYSA-N 0.000 description 1
- BFQFFNWLTHFJOZ-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C=2C=C3OCOC3=CC=2)=N1 BFQFFNWLTHFJOZ-UHFFFAOYSA-N 0.000 description 1
- MHDULSOPQSUKBQ-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-[2-(2-chlorophenyl)-4,5-diphenylimidazol-2-yl]-4,5-diphenylimidazole Chemical compound ClC1=CC=CC=C1C(N1C2(N=C(C(=N2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C(=CC=CC=2)Cl)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 MHDULSOPQSUKBQ-UHFFFAOYSA-N 0.000 description 1
- FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical compound CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-UHFFFAOYSA-N 0.000 description 1
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 1
- HZMXJTJBSWOCQB-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl prop-2-enoate Chemical compound COCCOCCOC(=O)C=C HZMXJTJBSWOCQB-UHFFFAOYSA-N 0.000 description 1
- QFNYOIKHNYCFRG-UHFFFAOYSA-N 2-(2-phenoxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC1=CC=CC=C1 QFNYOIKHNYCFRG-UHFFFAOYSA-N 0.000 description 1
- LEVFXWNQQSSNAC-UHFFFAOYSA-N 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-hexoxyphenol Chemical compound OC1=CC(OCCCCCC)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 LEVFXWNQQSSNAC-UHFFFAOYSA-N 0.000 description 1
- QRHHZFRCJDAUNA-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=CC(OC)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 QRHHZFRCJDAUNA-UHFFFAOYSA-N 0.000 description 1
- ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 description 1
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 description 1
- WXHVQMGINBSVAY-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 WXHVQMGINBSVAY-UHFFFAOYSA-N 0.000 description 1
- VQMHSKWEJGIXGA-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-6-dodecyl-4-methylphenol Chemical compound CCCCCCCCCCCCC1=CC(C)=CC(N2N=C3C=CC=CC3=N2)=C1O VQMHSKWEJGIXGA-UHFFFAOYSA-N 0.000 description 1
- VMSIYTPWZLSMOH-UHFFFAOYSA-N 2-(dodecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCOCC1CO1 VMSIYTPWZLSMOH-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- ZJRNXDIVAGHETA-GQCTYLIASA-N 2-[(e)-2-(3,4-dimethoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=C(OC)C(OC)=CC=C1\C=C\C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 ZJRNXDIVAGHETA-GQCTYLIASA-N 0.000 description 1
- MCNPOZMLKGDJGP-QPJJXVBHSA-N 2-[(e)-2-(4-methoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=CC(OC)=CC=C1\C=C\C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 MCNPOZMLKGDJGP-QPJJXVBHSA-N 0.000 description 1
- XOPKKHCDIAYUSK-SNAWJCMRSA-N 2-[(e)-2-(5-methylfuran-2-yl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound O1C(C)=CC=C1\C=C\C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 XOPKKHCDIAYUSK-SNAWJCMRSA-N 0.000 description 1
- PNDRGJCVJPHPOZ-ONEGZZNKSA-N 2-[(e)-2-(furan-2-yl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(\C=C\C=2OC=CC=2)=N1 PNDRGJCVJPHPOZ-ONEGZZNKSA-N 0.000 description 1
- SITYOOWCYAYOKL-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(3-dodecoxy-2-hydroxypropoxy)phenol Chemical compound OC1=CC(OCC(O)COCCCCCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 SITYOOWCYAYOKL-UHFFFAOYSA-N 0.000 description 1
- VVBVFVRWEMORTQ-UHFFFAOYSA-N 2-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxyphenoxy]ethyl 2-ethylhexanoate Chemical compound OC1=CC(OCCOC(=O)C(CC)CCCC)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 VVBVFVRWEMORTQ-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- CRHQOSXUXQSUQY-UHFFFAOYSA-N 2-ethylhexyl oxirane-2-carboxylate Chemical compound CCCCC(CC)COC(=O)C1CO1 CRHQOSXUXQSUQY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-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
- AAMHBRRZYSORSH-UHFFFAOYSA-N 2-octyloxirane Chemical compound CCCCCCCCC1CO1 AAMHBRRZYSORSH-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
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- OKISUZLXOYGIFP-UHFFFAOYSA-N 4,4'-dichlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1 OKISUZLXOYGIFP-UHFFFAOYSA-N 0.000 description 1
- FROCQMFXPIROOK-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol Chemical compound CC1=CC(C)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(O)=CC=2)O)=N1 FROCQMFXPIROOK-UHFFFAOYSA-N 0.000 description 1
- IFQUPKAISSPFTE-UHFFFAOYSA-N 4-benzoylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)C1=CC=CC=C1 IFQUPKAISSPFTE-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 1
- DRXGKQPTFWTTJW-UHFFFAOYSA-N 5-butoxy-2-[4-(4-butoxy-2-hydroxyphenyl)-6-(2,4-dibutoxyphenyl)-1,3,5-triazin-2-yl]phenol Chemical compound OC1=CC(OCCCC)=CC=C1C1=NC(C=2C(=CC(OCCCC)=CC=2)O)=NC(C=2C(=CC(OCCCC)=CC=2)OCCCC)=N1 DRXGKQPTFWTTJW-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
- NJCDRURWJZAMBM-UHFFFAOYSA-N 6-phenyl-1h-1,3,5-triazin-2-one Chemical compound OC1=NC=NC(C=2C=CC=CC=2)=N1 NJCDRURWJZAMBM-UHFFFAOYSA-N 0.000 description 1
- PGDIJTMOHORACQ-UHFFFAOYSA-N 9-prop-2-enoyloxynonyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCCOC(=O)C=C PGDIJTMOHORACQ-UHFFFAOYSA-N 0.000 description 1
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 102100033806 Alpha-protein kinase 3 Human genes 0.000 description 1
- 101710082399 Alpha-protein kinase 3 Proteins 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- BBCTYBCCROYGQQ-UHFFFAOYSA-N C1(CC2C(CC1)O2)CC[Si](CCCC)(CCCC)CCCC Chemical compound C1(CC2C(CC1)O2)CC[Si](CCCC)(CCCC)CCCC BBCTYBCCROYGQQ-UHFFFAOYSA-N 0.000 description 1
- BUVWUYLBRONSAD-UHFFFAOYSA-N C1(CC2C(CC1)O2)CC[Si](CCCCCCCC)(C)C Chemical compound C1(CC2C(CC1)O2)CC[Si](CCCCCCCC)(C)C BUVWUYLBRONSAD-UHFFFAOYSA-N 0.000 description 1
- RTGSPBBRFUIKKB-UHFFFAOYSA-N C1(CC2C(CC1)O2)CC[Si](O[Si](O[Si](O[Si](C)(C)C)(C)C)(C)C)(C)C Chemical compound C1(CC2C(CC1)O2)CC[Si](O[Si](O[Si](O[Si](C)(C)C)(C)C)(C)C)(C)C RTGSPBBRFUIKKB-UHFFFAOYSA-N 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- MXXGKZWWAPSWHN-UHFFFAOYSA-N CC(C)(C1=CC=CC=C1)C(C=C1)=C(C(C)(C)C2=CC=CC=C2)C(N2N=C(C=CC=C3)C3=N2)=C1O Chemical compound CC(C)(C1=CC=CC=C1)C(C=C1)=C(C(C)(C)C2=CC=CC=C2)C(N2N=C(C=CC=C3)C3=N2)=C1O MXXGKZWWAPSWHN-UHFFFAOYSA-N 0.000 description 1
- CNLWKRNDSSJSBN-UHFFFAOYSA-N CCCCCCCC[Si](C)(C)CCCOCC1OC1 Chemical compound CCCCCCCC[Si](C)(C)CCCOCC1OC1 CNLWKRNDSSJSBN-UHFFFAOYSA-N 0.000 description 1
- QSFZZPUFEFUQOY-UHFFFAOYSA-N CCCC[Si](CCCC)(CCCC)CCCOCC1OC1 Chemical compound CCCC[Si](CCCC)(CCCC)CCCOCC1OC1 QSFZZPUFEFUQOY-UHFFFAOYSA-N 0.000 description 1
- QXVZGRAAXLSLJD-UHFFFAOYSA-N C[Si](C)(CCC1CC2OC2CC1)C1CCCCC1 Chemical compound C[Si](C)(CCC1CC2OC2CC1)C1CCCCC1 QXVZGRAAXLSLJD-UHFFFAOYSA-N 0.000 description 1
- NZEYUORHKDEOIH-UHFFFAOYSA-N C[Si]1(C)O[Si](C)(C)O[Si](C)(CCC2CC3OC3CC2)O[Si](C)(C)O[Si](C)(C)O1 Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(CCC2CC3OC3CC2)O[Si](C)(C)O[Si](C)(C)O1 NZEYUORHKDEOIH-UHFFFAOYSA-N 0.000 description 1
- XLOOIYVUSDGEKM-UHFFFAOYSA-N C[Si]1(C)O[Si](C)(C)O[Si](C)(CCCOCC2OC2)O[Si](C)(C)O[Si](C)(C)O1 Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(CCCOCC2OC2)O[Si](C)(C)O[Si](C)(C)O1 XLOOIYVUSDGEKM-UHFFFAOYSA-N 0.000 description 1
- 229920001651 Cyanoacrylate Polymers 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 229920013731 Dowsil Polymers 0.000 description 1
- ZMDDERVSCYEKPQ-UHFFFAOYSA-N Ethyl (mesitylcarbonyl)phenylphosphinate Chemical compound C=1C=CC=CC=1P(=O)(OCC)C(=O)C1=C(C)C=C(C)C=C1C ZMDDERVSCYEKPQ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- NQSMEZJWJJVYOI-UHFFFAOYSA-N Methyl 2-benzoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NQSMEZJWJJVYOI-UHFFFAOYSA-N 0.000 description 1
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- HEQDCEOZBRONNB-UHFFFAOYSA-N [dimethyl(2-trimethoxysilylethyl)silyl]oxy-dimethyl-(2-trimethoxysilylethyl)silane Chemical compound CO[Si](OC)(OC)CC[Si](C)(C)O[Si](C)(C)CC[Si](OC)(OC)OC HEQDCEOZBRONNB-UHFFFAOYSA-N 0.000 description 1
- HVWUCQAXPIPNFA-UHFFFAOYSA-N [dimethyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silyl]oxy-dimethyl-trimethylsilyloxysilane Chemical compound C1C(CC[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C)CCC2OC21 HVWUCQAXPIPNFA-UHFFFAOYSA-N 0.000 description 1
- CAGLMBNACHKRDQ-UHFFFAOYSA-N [dimethyl-[3-(oxiran-2-ylmethoxy)propyl]silyl]oxy-[dimethyl(trimethylsilyloxy)silyl]oxy-dimethylsilane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)CCCOCC1OC1 CAGLMBNACHKRDQ-UHFFFAOYSA-N 0.000 description 1
- RBIDBLBWLVIZMS-UHFFFAOYSA-N [dimethyl-[3-(oxiran-2-ylmethoxy)propyl]silyl]oxy-dimethyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)CCCOCC1CO1 RBIDBLBWLVIZMS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000011358 absorbing material Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- XVAMCHGMPYWHNL-UHFFFAOYSA-N bemotrizinol Chemical compound OC1=CC(OCC(CC)CCCC)=CC=C1C1=NC(C=2C=CC(OC)=CC=2)=NC(C=2C(=CC(OCC(CC)CCCC)=CC=2)O)=N1 XVAMCHGMPYWHNL-UHFFFAOYSA-N 0.000 description 1
- 229960004101 bemotrizinol Drugs 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- DJBAOXYQCAKLPH-UHFFFAOYSA-M bis(4-tert-butylphenyl)iodanium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F.C1=CC(C(C)(C)C)=CC=C1[I+]C1=CC=C(C(C)(C)C)C=C1 DJBAOXYQCAKLPH-UHFFFAOYSA-M 0.000 description 1
- VGZKCAUAQHHGDK-UHFFFAOYSA-M bis(4-tert-butylphenyl)iodanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(C(C)(C)C)=CC=C1[I+]C1=CC=C(C(C)(C)C)C=C1 VGZKCAUAQHHGDK-UHFFFAOYSA-M 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
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000011231 conductive filler Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=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])[H] 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- RSMWFWMIVSBTKV-UHFFFAOYSA-N dimethyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]-phenylsilane Chemical compound C1CC2OC2CC1CC[Si](C)(C)C1=CC=CC=C1 RSMWFWMIVSBTKV-UHFFFAOYSA-N 0.000 description 1
- UNCZZCYKSPOECH-UHFFFAOYSA-N dimethyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]-trimethylsilyloxysilane Chemical compound C1C(CC[Si](C)(C)O[Si](C)(C)C)CCC2OC21 UNCZZCYKSPOECH-UHFFFAOYSA-N 0.000 description 1
- UMZAYKAZMGVWND-UHFFFAOYSA-N dimethyl-[3-(oxiran-2-ylmethoxy)propyl]-phenylsilane Chemical compound C=1C=CC=CC=1[Si](C)(C)CCCOCC1CO1 UMZAYKAZMGVWND-UHFFFAOYSA-N 0.000 description 1
- OYWALDPIZVWXIM-UHFFFAOYSA-N dimethyl-[3-(oxiran-2-ylmethoxy)propyl]-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C)CCCOCC1CO1 OYWALDPIZVWXIM-UHFFFAOYSA-N 0.000 description 1
- OWZDULOODZHVCQ-UHFFFAOYSA-N diphenyl-(4-phenylsulfanylphenyl)sulfanium Chemical compound C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1SC1=CC=CC=C1 OWZDULOODZHVCQ-UHFFFAOYSA-N 0.000 description 1
- WEYUQUMMYNRIPP-UHFFFAOYSA-M diphenyl-(4-phenylsulfanylphenyl)sulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1SC1=CC=CC=C1 WEYUQUMMYNRIPP-UHFFFAOYSA-M 0.000 description 1
- UMIKAXKFQJWKCV-UHFFFAOYSA-M diphenyliodanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C=1C=CC=CC=1[I+]C1=CC=CC=C1 UMIKAXKFQJWKCV-UHFFFAOYSA-M 0.000 description 1
- CQZCVYWWRJDZBO-UHFFFAOYSA-N diphenyliodanium;nitrate Chemical compound [O-][N+]([O-])=O.C=1C=CC=CC=1[I+]C1=CC=CC=C1 CQZCVYWWRJDZBO-UHFFFAOYSA-N 0.000 description 1
- SBQIJPBUMNWUKN-UHFFFAOYSA-M diphenyliodanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C=1C=CC=CC=1[I+]C1=CC=CC=C1 SBQIJPBUMNWUKN-UHFFFAOYSA-M 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005530 etching Methods 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
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000012767 functional filler Substances 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- JUYQFRXNMVWASF-UHFFFAOYSA-M lithium;phenyl-(2,4,6-trimethylbenzoyl)phosphinate Chemical compound [Li+].CC1=CC(C)=CC(C)=C1C(=O)P([O-])(=O)C1=CC=CC=C1 JUYQFRXNMVWASF-UHFFFAOYSA-M 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical class [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- LUCXVPAZUDVVBT-UHFFFAOYSA-N methyl-[3-(2-methylphenoxy)-3-phenylpropyl]azanium;chloride Chemical compound Cl.C=1C=CC=CC=1C(CCNC)OC1=CC=CC=C1C LUCXVPAZUDVVBT-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- PNXSDOXXIOPXPY-DPTVFECHSA-N n-hydroxy-5-norbornene-2,3-dicarboximide perfluoro-1-butanesulfonate Chemical compound C([C@H]1C=C2)[C@H]2C2C1C(=O)N(OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C2=O PNXSDOXXIOPXPY-DPTVFECHSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000005304 optical glass Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 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
- 238000012360 testing method Methods 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 1
- NRYWFNLVRORSCA-UHFFFAOYSA-N triethoxy(6-triethoxysilylhexyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCCCC[Si](OCC)(OCC)OCC NRYWFNLVRORSCA-UHFFFAOYSA-N 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- WTLYGTAYMWRFFR-UHFFFAOYSA-N triethyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](CC)(CC)CC)CCC2OC21 WTLYGTAYMWRFFR-UHFFFAOYSA-N 0.000 description 1
- FTNCLFLVKLFJPL-UHFFFAOYSA-N triethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CC[Si](CC)(CC)CCCOCC1CO1 FTNCLFLVKLFJPL-UHFFFAOYSA-N 0.000 description 1
- ZZJNLOGMYQURDL-UHFFFAOYSA-M trifluoromethanesulfonate;tris(4-methylphenyl)sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(C)=CC=C1[S+](C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZZJNLOGMYQURDL-UHFFFAOYSA-M 0.000 description 1
- HHMQUQRJNPTPAJ-UHFFFAOYSA-M trifluoromethanesulfonate;tris(4-tert-butylphenyl)sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(C(C)(C)C)=CC=C1[S+](C=1C=CC(=CC=1)C(C)(C)C)C1=CC=C(C(C)(C)C)C=C1 HHMQUQRJNPTPAJ-UHFFFAOYSA-M 0.000 description 1
- BDUQYMJRXBPVEA-UHFFFAOYSA-N trihexyl-[2-(7-oxabicyclo[4.1.0]heptan-3-yl)ethyl]silane Chemical compound C1C(CC[Si](CCCCCC)(CCCCCC)CCCCCC)CCC2OC21 BDUQYMJRXBPVEA-UHFFFAOYSA-N 0.000 description 1
- JUVVJJIUMQQDEP-UHFFFAOYSA-N trihexyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCCCCC[Si](CCCCCC)(CCCCCC)CCCOCC1CO1 JUVVJJIUMQQDEP-UHFFFAOYSA-N 0.000 description 1
- GFKCWAROGHMSTC-UHFFFAOYSA-N trimethoxy(6-trimethoxysilylhexyl)silane Chemical compound CO[Si](OC)(OC)CCCCCC[Si](OC)(OC)OC GFKCWAROGHMSTC-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- YSIQPJVFCSCUMU-UHFFFAOYSA-N trimethyl-[methyl-[3-(oxiran-2-ylmethoxy)propyl]-trimethylsilyloxysilyl]oxysilane Chemical compound C[Si](C)(C)O[Si](C)(O[Si](C)(C)C)CCCOCC1CO1 YSIQPJVFCSCUMU-UHFFFAOYSA-N 0.000 description 1
- VMJFYMAHEGJHFH-UHFFFAOYSA-M triphenylsulfanium;bromide Chemical compound [Br-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 VMJFYMAHEGJHFH-UHFFFAOYSA-M 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
-
- 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
- C08F290/068—Polysiloxanes
-
- 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
- C08F290/08—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 side groups
- C08F290/14—Polymers provided for in subclass C08G
- C08F290/148—Polysiloxanes
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/223—Di-epoxy compounds together with monoepoxy compounds
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
- C08G59/306—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing silicon
-
- 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
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- 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
- C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- 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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/08—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C09D151/085—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds on to polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
Definitions
- the present invention relates to UV latitudinal curable compositions curable by actinic rays, e.g.
- the present invention relates to an ultraviolet curable composition in which the resulting cured product has a low viscosity, is excellent in coatability, and has an ultraviolet shielding function.
- the curable composition of the present invention is suitable as an insulating material for electronic and electrical devices, especially as a material for use as a coating agent. Furthermore, it has excellent applicability and excellent wettability to substrates, and is useful as an injection molding material and an inkjet printing material.
- silicone resins Due to its high heat resistance and excellent chemical stability, silicone resins have been used as coating agents, potting agents, insulating materials, etc. for electronic and electrical devices. Among silicone resins, UV-curable silicone compositions have also been reported so far.
- Touch panels are used in various display devices such as mobile devices, industrial equipment, and car navigation systems. In order to improve the detection sensitivity, it is necessary to suppress the electrical influence from the light emitting parts such as light emitting diodes (LED) and organic EL devices (OLED). placed.
- LED light emitting diodes
- OLED organic EL devices
- thin display devices such as OLED have a structure in which many functional thin layers are laminated.
- studies have begun to improve the reliability of display devices, particularly flexible display devices as a whole, by laminating an insulating layer having an ultraviolet shielding function on a touch screen layer.
- an inkjet printing method is adopted as a method for processing an organic layer. Therefore, materials that can be processed by the inkjet printing method are also required for the insulating layer.
- a UV-curable resin composition containing a compound having a UV-absorbing function is known.
- Japanese Patent No. 6729776 discloses an ultraviolet absorbing material which is a salt product of an acrylic resin having a cationic group and an anionic dye, and an acrylic photocurable composition containing the same.
- this composition has UV absorption function at 380-400 nm, it is not suitable for cast molding and inkjet printing methods because it is diluted with solvent.
- JP-A-2019-194309 and JP-A-2020-139108 disclose an acrylic pressure-sensitive adhesive composition for image display devices containing an ultraviolet absorber. Neither composition can be applied by inkjet printing due to its high viscosity.
- UV curable resin compositions having an ultraviolet absorbing function are well known, and the mechanical properties of the cured product can be easily adjusted, and excellent workability for coating on a substrate, especially There is still a need for UV curable compositions with low viscosity.
- the present invention has a high ability to adjust the mechanical properties of the product obtained by curing, has a function of absorbing ultraviolet rays, especially ultraviolet rays of 360 to 400 nm, and has excellent workability when applied to a substrate.
- to provide curable compositions containing silicon atoms particularly UV curable compositions, particularly UV curable organopolysiloxane compositions.
- the present invention provides the following (S1) or (S2): (S1) organopolysiloxane and/or organosilane having an ultraviolet-curable functional group; (S2) selected from (A) a compound having a UV-curable functional group and having or not having a silicon atom and (B) a mixture consisting of an organopolysiloxane having no UV-curable functional group;
- the UV-curable composition obtained by using the component (S) containing one or more organosilicon compounds and the compound (C) having UV-absorbing ability in combination has a good UV-absorbing function and a low viscosity.
- the workability when applied to a base material is excellent, and that the cured product exhibits excellent mechanical property adjustment ability.
- the present invention provides one or more components selected from the group consisting of components (S1) below, or one or more components (S) selected from the group consisting of components (S2) 90 to 99.99 Part by mass: (S1) organopolysiloxane and/or organosilane having an ultraviolet-curable functional group; (S2) (A) a compound having a UV-curable functional group and having or not having a silicon atom, and (B) an organopolysiloxane having no UV-curable functional group at 5:95-95 : a mixture containing in a mass ratio of 5 (A:B), and (C) 0.01 to 10 parts by mass of an ultraviolet absorbing compound (where the total of component (S) and component (C) is 100 parts by mass).
- This UV-curable composition has a good UV-absorbing function, a low viscosity, excellent workability when applied to a substrate, and a cured product thereof exhibiting excellent mechanical property controllability.
- the component (S) contains an organopolysiloxane (S1) having an ultraviolet curable functional group or an organopolysiloxane (B) having no ultraviolet curable functional group. It is preferably an organopolysiloxane composition.
- the above ultraviolet curable composition of the present invention is applied to an arbitrary substrate so that the thickness after curing is 10 ⁇ m, and the integrated amount of light at at least one wavelength selected from wavelengths of 365 to 405 nm is 2.
- the composition can be cured at the time of completion of irradiation or within 5 minutes after the completion of irradiation when light irradiation is carried out so as to achieve ⁇ 8 J/cm 2 . It is characterized by having a transmittance of 98% or more and a light transmittance of 50% or less at at least one point in the wavelength range of 360 to 405 nm.
- the meaning that the light transmittance of the cured product is 50% or less at at least one point in the wavelength range of 360 to 405 nm means that when the light transmittance of the cured product is measured over the range of 300 to 800 nm, the wavelength It means that the light transmittance is 50% or less at least at one point in the range of 360 to 405 nm.
- the meaning that the ultraviolet curable composition is cured means that the composition does not stick to the finger when the surface of the composition is touched with a finger after light irradiation.
- the curable composition of the present invention cures by forming bonds with UV-curable functional groups.
- the curable composition of the present invention preferably contains substantially no organic solvent.
- the curable composition of the present invention preferably has a viscosity of 500 mPa ⁇ s or less as a whole composition measured at 25°C using an E-type viscometer.
- the wavelength range in which the 10 ⁇ m-thick cured product obtained from the curable composition of the present invention exhibits the lowest light transmittance is preferably 385 to 400 nm.
- the wavelength range of 385 to 400 nm that exhibits the lowest light transmittance is the wavelength that exhibits the lowest light transmittance within the measurement wavelength range when the light transmittance of the cured product is measured in the range of 300 nm to 800 nm. area.
- the ultraviolet absorbing compound which is the component (C) in the curable composition, is preferably a compound having a maximum absorption wavelength in the wavelength range of 340-420 nm.
- Component (S1) and component (S2) (A) in the curable composition of the present invention have an ultraviolet-curable functional group and a silicon atom-containing compound having the average composition formula: R c R′ d SiO (4-cd)/2 (2)
- R is an ultraviolet curable functional group
- R' is a group selected from monovalent hydrocarbon groups, hydroxyl groups, and alkoxy groups excluding UV-reactive UV-curable functional groups
- c and d are numbers satisfying the following conditions: 1 ⁇ c+d ⁇ 4 and 0.05 ⁇ c/(c+d) ⁇ 0.25, and the number of R in the molecule is one.
- Component (S1) and component (S2) (A) in the curable composition of the present invention have an ultraviolet-curable functional group and a silicon atom-containing compound having the average composition formula: R a R′ b SiO (4-ab)/2 (1)
- R is an ultraviolet curable functional group
- R' is a group selected from a monovalent hydrocarbon group excluding an ultraviolet curable functional group, a hydroxyl group, and an alkoxy group
- a and b are numbers satisfying the following conditions: 1 ⁇ a+b ⁇ 3 and 0.01 ⁇ a/(a+b) ⁇ 0.34, and have at least two R in the molecule.
- Linear, branched or cyclic organopolysiloxane represented by is preferred.
- the compound (S1) and component (S2) of the curable composition of the present invention having an ultraviolet-curable functional group and having a silicon atom is represented by the following formula (3′): (In formula (3′), only one UV-curable functional group exists in the molecule among all R 1 to R 8 groups; the other R 1 to R 8 are each independently unsubstituted or fluorine is a monovalent hydrocarbon group substituted with; n is a numerical value of 0 or more and 3 or less), Or the following formula (5′): (In formula (5′), each R is independently a group selected from an ultraviolet-curable functional group and an unsubstituted or fluorine-substituted monovalent hydrocarbon group, and x is an integer of 3 to 5.
- R is an ultraviolet-curable functional group
- R' is a group selected from monovalent hydrocarbon groups excluding the ultraviolet-curable functional group, hydroxyl group, and alkoxy group.
- It is preferably an organopolysiloxane and/or an organosilane having one UV-curable functional group in the molecule, which is selected from the group consisting of organosilanes which are selected from the group consisting of organosilanes.
- the component (S1) organopolysiloxane and the component (S2) (A) a compound having a UV-curable functional group and having a silicon atom are represented by the following formula (3): (in formula (3), two or more of all R 1 to R 8 groups on average per molecule are UV-curable functional groups; the other R 1 to R 8 are each independently unsubstituted or is a fluorine-substituted monovalent hydrocarbon group; n is a numerical value at which the viscosity of the organopolysiloxane represented by formula (3) is 1 to 1000 mPa s at 25° C., and n is 0; Organopolysiloxane represented by Average unit formula: (R 3 SiO 1/2 ) e (R 2 SiO 2/2 ) f (RSiO 3/2 ) g (SiO 4/2 ) h (4) (In formula (4), each R is independently a group selected from an ultraviolet-curable functional
- the component (S1) in the curable composition has an average of two UV-curable functional groups per molecule.
- the component (S1) in the curable composition is an organopolysiloxane having one UV-curable functional group in its molecule.
- the UV-curable functional groups of component (S1) and component (A) in the curable composition of the present invention include acryloxy group-containing groups, methacryloxy group-containing groups, epoxy group-containing groups, oxetane group-containing groups, and vinyl ether group-containing groups. It is preferably a functional group selected from the group consisting of groups.
- the curable composition preferably contains component (S1) as component (S). It is further preferred that component (S1) is an epoxy-functional organopolysiloxane.
- the curable composition preferably contains component (S2) as component (S). More preferably, component (S2)(A) is a compound having an acryloxy group.
- component (A) is a compound having an acryloxy group and component (B) is an organopolysiloxane having an alkenyl group.
- the curable composition contains component (S2) and component (A) is a silicon-free compound.
- the curable composition contains component (S2) and component (A) is a compound having a silicon atom.
- the curable composition contains component (S1) as component (S), and component (S1) is (S1-1) one or more organopolysiloxanes having an average of two or more epoxy group-containing groups per molecule, and (S1-2) 1 having one epoxy group-containing group per molecule
- component (S1-1) and component (S1-2) contain at least one organosilicon compound selected from the group consisting of at least one organopolysiloxane and/or organosilane at a ratio of 100/0 to 0/100 (S1- It is preferably a mixture containing at a mass ratio of 1/S1-2).
- the curable composition contains component (S1) as component (S), and component (S1) is (S1-2-1) 1,1,1 , 3,5,5,5-heptamethyl-3-[2-(3,4-epoxycyclohexyl)ethyl]trisiloxane, or (S1-2-1) 1,1,1,3,5, A mixture of 5,5-heptamethyl-3-[2-(3,4-epoxycyclohexyl)ethyl]trisiloxane and at least one compound selected from the following group (S1-1-1),
- the mass ratio is in the range of 100/0 to 0/100 (amount of S-2-1/total amount of compounds selected from the group of S1-1-1): (S1-1-1): 1,3-bis[2-(3,4-epoxycyclohexyl)ethyl]-1,1,3,3-tetramethyldisiloxane, 1,5-bis[2-(3,4-epoxycyclohexy
- the curable composition contains a component (S2) containing components (A) and (B) as component (S), and component (A) is an ultraviolet curing It is a compound having one acryloxy group as a functional group, or a mixture of two or more compounds having one acryloxy group.
- the curable composition contains component (S2), and component (A) in the composition has one or more acryloxy groups as UV-curable functional groups. and one or more compounds having two or more acryloxy groups.
- the curable composition contains component (S2) containing components (A) and (B) as component (S), and component (A) contains one It is a compound having the above acryloxy group and no silicon atom.
- the curable composition contains component (S2) containing components (A) and (B) as component (S), and component (B) is the following component ( B1) and (B2) are one or more components selected from the group consisting of: (B1) an organopolysiloxane having 3 or more alkenyl groups in one molecule and no UV-curable functional group; (B2) Organopolysiloxane having two or more alkenyl groups per molecule, a vinyl group content of 5% by mass or more, and no UV-curable functional groups.
- the curable composition comprises component (S2) containing components (A) and (B) as component (S), and component (B) is the average composition formula: R a R′ b SiO (4-ab)/2 (7)
- R is an alkenyl group
- R' is a group selected from monovalent hydrocarbon groups excluding alkenyl groups, hydroxyl groups, and alkoxy groups
- a and b are numbers satisfying the following conditions: 1 ⁇ a+b ⁇ 3 and 0.1 ⁇ a/(a+b) ⁇ 1.0, and have at least two R in the molecule.
- It is a linear, branched or cyclic organopolysiloxane represented by
- the curable composition contains, as component (S), component (S2) containing components (A) and (B), and component (B) organopolysiloxane is the following formula (8):
- component (S) containing components (A) and (B)
- component (B) organopolysiloxane is the following formula (8):
- formula (8) among all R 1 to R 8 groups, two or more alkenyl groups are present in the molecule; the other R 1 to R 8 are each independently unsubstituted or substituted with fluorine an organopolysiloxane represented by a monovalent hydrocarbon group;
- n is a numerical value of 1 or more and 1,000 or less;
- each R is independently a group selected from an alkenyl group and an unsubstituted or fluorine-substi
- each R is independently a group selected from an alkenyl group and an unsubstituted or fluorine-substituted monovalent hydrocarbon group, x is an integer of 3 to 10, and in the molecule a cyclic organopolysiloxane represented by having at least two alkenyl groups in and one or more organopolysiloxanes having two or more alkenyl groups in the molecule, selected from the group consisting of mixtures of these organopolysiloxanes.
- component (B) comprises an organopolysiloxane having (RSiO 3/2 ) units.
- component (B) is an organopolysiloxane having 3 or more alkenyl groups in one molecule.
- component (B) is an organopolysiloxane having an alkenyl group
- the alkenyl group of component (B) is preferably an alkenyl group having 3 to 8 carbon atoms.
- the viscosity of the above-described curable composition of the present invention can be appropriately set according to the application, but the viscosity of the entire composition measured at 25 ° C. using an E-type viscometer is in the range of 5 to 60 mPa s. is preferably 5 to 30 mPa.s. More preferably, it is in the range of s.
- the present invention also provides a cured product obtained by curing the ultraviolet curable composition.
- a cured product having a thickness of 10 ⁇ m obtained from the ultraviolet curable composition of the present invention preferably has the lowest light transmittance of 25% or less in the wavelength range of 360 to 405 nm.
- the lowest value of light transmittance in the wavelength range of 360 to 405 nm of the 10 ⁇ m-thick cured product obtained from the ultraviolet-curable composition of the present invention is 10% or less.
- the present invention further provides an insulating coating agent containing the above UV-curable composition.
- the UV-curable composition of the present invention is useful as an insulating coating agent.
- the present invention further provides a method of using a cured product of the UV-curable composition as an insulating coating layer.
- the present invention further provides a display device, such as a liquid crystal display, an organic EL display, and an organic EL flexible display, including a layer comprising a cured product of the ultraviolet curable composition.
- a display device such as a liquid crystal display, an organic EL display, and an organic EL flexible display, including a layer comprising a cured product of the ultraviolet curable composition.
- the ultraviolet curable composition of the present invention comprises the following (S1) or component (S2): (S1) organopolysiloxane and/or organosilane having an ultraviolet-curable functional group; (S2) (A) a compound having a UV-curable functional group and having or not having a silicon atom and (B) an organopolysiloxane having no UV-curable functional group at 5:95 to 95: A mixture containing a mass ratio of 5 (A:B), 90 to 99.99 parts by mass of one or more components (S) selected from (total amount of components (S)), and (C) UV-absorbing compound 0.01 to 10 parts by mass (however, the total of component (S) and component (C) is 100 parts by mass)
- An ultraviolet curable composition containing The composition is applied to an arbitrary substrate so that the thickness after curing is 10 ⁇ m, and light irradiation is performed so that the integrated amount of light at at least one wavelength selected from 365 to
- the composition can be cured at the time of completion of irradiation or within 5 minutes thereafter, and the obtained cured product with a thickness of 10 ⁇ m has a light transmittance of 98% or more at a wavelength of 450 nm, and a wavelength range It is characterized by having a light transmittance of 50% or less at least at one point from 360 to 405 nm.
- the ultraviolet-curable composition of the present invention may optionally contain further components selected from radical photopolymerization initiators and various additives in addition to the above component (S) and component (C).
- polysiloxane refers to a siloxane unit (Si—O) having a degree of polymerization of 2 or more, that is, having an average of 2 or more Si—O bonds per molecule. It includes siloxane oligomers such as disiloxanes, trisiloxanes, tetrasiloxanes, etc., to siloxane polymers with a higher degree of polymerization.
- the ultraviolet curable composition of the present invention may be diluted with an organic solvent, but preferably does not contain an organic solvent.
- Free of organic solvent means that the content of organic solvent is less than 0.05% by weight of the total composition, preferably below the analytical limit using an analytical method such as gas chromatography.
- a desired viscosity can be achieved without using an organic solvent by adjusting the molecular structure and molecular weight of component (S1), component (A), and component (B).
- the component (S) of the present invention is the main component of the UV-curable composition.
- the curable composition comprises (S1) an organopolysiloxane and/or organosilane having UV-curable functional groups as component (S).
- the curable composition comprises (S2) (A) a compound having a UV-curable functional group and free of or containing silicon atoms and (B) It contains a mixture containing organopolysiloxanes without UV-curable functional groups in a weight ratio of 5:95 to 95:5.
- the curable composition of the present invention contains either one of the component (S1) and the component (S2), but other optional components are added on the condition that the combination of (S1) and (S2) is not applicable.
- the component (S1) may be used in combination with a compound having a UV-curable functional group and no silicon atom.
- UV-curable organic group can be used as the ultraviolet-curable functional group of the component (S1) and the component (A) in the curable composition.
- UV-curable functional groups include acryloxy group-containing groups, methacryloxy group-containing groups, epoxy group-containing groups, oxetane group-containing groups, vinyl ether group-containing groups, and maleimide group-containing groups.
- Acryloxy group-containing groups and epoxy group-containing groups are preferably used in consideration of the properties.
- component (S1) an ultraviolet curable organosilicon compound selected from the group consisting of acryloxy group-functional polysiloxanes, epoxy group-functional polysiloxanes, acryloxy group-functional organosilanes, and epoxy-functional organosilanes, or are preferred.
- one or more organosilicon compounds selected from the group consisting of epoxy-functional polysiloxanes and epoxy-functional organosilanes can be particularly preferably used as component (S1).
- component (S2) is a mixture of component (A) and component (B) at a ratio of 5:95 to 95:5 (mass ratio) as component (S). including.
- the compound that can be used as component (A) is not particularly limited as long as it is a compound that has an ultraviolet-curable functional group and either has a silicon atom or does not have a silicon atom, and its structure is not particularly limited. It is preferable to use a compound selected from an acryloxy group-functional organic compound and an epoxy group-functional organic compound, and it is particularly preferable to use an acryloxy group-functional organic compound.
- component (B) used in combination with component (A) is an organopolysiloxane having no UV-curable functional group, and its structure is not particularly limited. Organopolysiloxanes having two or more alkenyl groups in them are preferred.
- the component (S1) of the present invention includes one or more organopolysiloxanes (S1-A) having an average of two or more UV-curable functional groups in one molecule, and one ultraviolet ray in one molecule.
- a particularly preferred compound as the component (S1-A) is an organopolysiloxane (S1-1) having an epoxy group-containing group as an ultraviolet-curable functional group
- a particularly preferred compound as the component (S1-B) is an ultraviolet-curable Organopolysiloxane and/or organosilane (S1-2) having an epoxy group-containing group as a functional group.
- An aspect in which only the component (S1-2) is used as the component (S1) is also one of the preferred aspects.
- the component (S1) contains one or more organopolysiloxanes having an average of two or more UV-curable functional groups in one molecule (S1-A)
- the component (D) does not exist.
- the cross-linking reaction proceeds in the composition as a whole. That is, component (D) is a cross-linking component that may optionally be used depending on the type of component (S1).
- the component (S1) has a viscosity at 25°C of 1 to 1000 mPa ⁇ s, particularly 1 to 500 mPa.s. s, more preferably 5 to 100 mPa ⁇ s, particularly preferably 5 to 60 mPa ⁇ s, and most preferably 5 to 30 mPa ⁇ s.
- component (S1) contains 1 to 20, preferably 1 to 12, more preferably 1 to 8, and most preferably 1 to 5 silicon atoms per molecule.
- Component (S) is the main component of the curable composition, and one or more compounds selected from component (S1) or one or more compounds selected from component (S2) can be used.
- Component (S1) is, as described above, one or more organopolysiloxanes (S1-A) having an average of two or more UV-curable functional groups in one molecule, and one UV-curable functional group in one molecule. It can be one or more organopolysiloxanes and/or organosilanes (S1-B) with functional groups, or any mixture thereof.
- Component (S1-A) polysiloxane having an average of two or more UV-curable functional groups in one molecule>
- Component (S1-A) polysiloxane has the following average composition formula: R a R′ b SiO (4-ab)/2 (1) It is a linear, branched or cyclic, preferably linear or branched, particularly preferably linear organopolysiloxane represented by.
- R is an ultraviolet curable functional group
- R' is a group selected from monovalent hydrocarbon groups, hydroxyl groups, and alkoxy groups, excluding UV-curable functional groups
- a and b satisfy the following conditions: 1 ⁇ a+b ⁇ 3 and 0.01 ⁇ a/(a+b) ⁇ 0.34, preferably 2 ⁇ a+b ⁇ 3 and 0.05 ⁇ a/(a+b) ⁇ 0.34 It is a satisfying number and has at least 2 R's in one molecule on average.
- the UV-curable functional group represented by R in formula (1) is an organic group capable of forming a bond between itself by UV irradiation in the presence or absence of a photoinitiator.
- Examples of UV-curable functional groups include radically polymerizable groups and cationic polymerizable groups.
- the radically polymerizable group is not particularly limited as long as it is a functional group capable of forming a new bond, particularly a bond between radically polymerizable groups, by a radical reaction mechanism. Organic groups containing any group can be mentioned.
- radically polymerizable groups examples include groups such as acryloxypropyl, methacryloxypropyl, acrylamidopropyl, methacrylamidopropyl, and 3-(N-maleimido)propyl as radically polymerizable groups.
- radically polymerizable group an acryloxy group-containing group is preferred.
- Examples of cationic polymerizable groups include groups such as vinyl ether groups, epoxy group-containing groups, and oxetane group-containing groups, such as CH 2 ⁇ CH—O—(CH 2 ) n — (n is an integer of 3 to 20), groups such as glycidyloxy-(CH 2 ) n — (n is an integer from 3 to 20), 3,4-epoxycyclohexyl-(CH 2 ) n — (n is an integer from 2 to 20); be done.
- the cationic polymerizable group is preferably an epoxy group-containing group such as the aforementioned glycidyloxy-(CH 2 ) n - group.
- the UV-curable functional group represented by R in formula (1) is preferably an epoxy group-containing group.
- Particularly preferred groups include glycidyloxyalkyl groups, such as glycidyloxypropyl groups, and epoxycyclohexylalkyl groups, especially 3,4-epoxycyclohexylethyl groups.
- the linear, branched, or cyclic organopolysiloxane represented by the average composition formula has an average of at least two UV-curable functional groups (R) per molecule, but the UV-curable functional group is preferably 2 to 6, more preferably 2 to 4, particularly preferably 2 to 3, and most preferably 2 on average per molecule.
- Two or more different types of UV-curable functional groups may be present in one molecule. For example, when two or more epoxy group-containing groups are present in one molecule, they may be the same or different.
- the monovalent hydrocarbon group includes unsubstituted monovalent hydrocarbon groups and fluorine-substituted monovalent hydrocarbon groups.
- the unsubstituted or fluorine-substituted monovalent hydrocarbon group is preferably a group selected from unsubstituted or fluorine-substituted alkyl, cycloalkyl, arylalkyl, and aryl groups having 1 to 20 carbon atoms. be.
- alkyl group examples include groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, pentyl, and octyl, with the methyl group being particularly preferred.
- cycloalkyl group examples include cyclopentyl and cyclohexyl.
- arylalkyl group examples include benzyl and phenylethyl groups.
- the aryl group examples include a phenyl group and a naphthyl group.
- fluorine-substituted monovalent hydrocarbon groups examples include 3,3,3-trifluoropropyl and 3,3,4,4,5,5,6,6,6-nonafluorohexyl groups. .
- a 3,3,3-trifluoropropyl group is preferred as the fluorine-substituted monovalent hydrocarbon group.
- R' represents an alkoxy group
- the alkoxy group preferably has 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, particularly preferably 1 or 2 carbon atoms, and most preferably 1 carbon atom.
- R' is not a UV curable functional group.
- the organopolysiloxane represented by the above formula (1) has a viscosity at 25° C. of 1 to 1000 mPa s, 1 to 500 mPa s, 5 to 100 mPa s, or 5 to 60 mPa s, most preferably 5 ⁇ 30 mPa ⁇ s.
- the viscosity of the organopolysiloxane can be adjusted by varying the ratio of a and b in formula (1) and the molecular weight.
- the organopolysiloxane represented by formula (1) preferably has an average of 2 to 20, more preferably 2 to 12, still more preferably 2 to 8, and most preferably 2 to 5 silicon atoms per molecule.
- component (S1-A) organopolysiloxane is Formula (3) below: It is a compound represented by
- the organopolysiloxane represented by formula (3) has an average of two or more UV-curable functional groups per molecule.
- two or more on average of all R 1 to R 8 groups are UV-curable functional groups per molecule.
- UV-curable functional groups are organic groups that are capable of forming bonds between each other upon irradiation with UV light in the presence or absence of a photoinitiator. Examples of UV-curable functional groups include radically polymerizable groups and cationic polymerizable groups.
- the radically polymerizable group is not particularly limited as long as it is a functional group capable of forming a new bond, particularly a bond between radically polymerizable groups, by a radical reaction mechanism.
- Organic groups containing any group can be mentioned. Specific examples include groups such as acryloxypropyl, methacryloxypropyl, acrylamidopropyl, methacrylamidopropyl, and 3-(N-maleimido)propyl as radically polymerizable groups.
- Examples of cationic polymerizable groups include groups such as vinyl ether groups, epoxy group-containing groups, and oxetane group-containing groups, such as CH 2 ⁇ CH—O—(CH 2 ) n — (n is an integer of 3 to 20), groups such as glycidyloxy-(CH 2 ) n — (n is an integer from 3 to 20), 3,4-epoxycyclohexyl-(CH 2 ) n — (n is an integer from 2 to 20); be done.
- the UV-curable functional group one or more epoxy group-containing groups are preferable. Particularly preferred groups are glycidyloxyalkyl groups, especially 3-glycidyloxypropyl groups, epoxycyclohexylalkyl groups, especially 3,4-epoxycyclohexylethyl groups.
- each of R 1 to R 8 other than the UV-curable functional group is independently an unsubstituted or fluorine-substituted monovalent hydrocarbon group, preferably an unsubstituted or It is a group selected from fluorine-substituted alkyl, cycloalkyl, arylalkyl, and aryl groups.
- alkyl group include groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, pentyl, and octyl, with the methyl group being particularly preferred.
- Examples of the cycloalkyl group include cyclopentyl and cyclohexyl.
- Examples of the arylalkyl group include benzyl and phenylethyl groups.
- Examples of the aryl group include a phenyl group and a naphthyl group.
- Examples of fluorine-substituted monovalent hydrocarbon groups include 3,3,3-trifluoropropyl and 3,3,4,4,5,5,6,6,6-nonafluorohexyl groups. .
- a 3,3,3-trifluoropropyl group is preferred as the fluorine-substituted monovalent hydrocarbon group.
- the number of UV-curable functional groups possessed by the organopolysiloxane of formula (3), which is the component (S1-A), is on average 2 to 6, preferably 2 to 5, more preferably 2 to 5 per molecule as a whole. 4, particularly preferably 2 to 3, most preferably 2.
- one of R 1 to R 3 and one of R 6 to R 8 in formula (3) are preferably UV-curable functional groups. Furthermore, it is particularly preferred that only one of R 1 to R 3 and one of R 6 to R 8 in formula (3) is an ultraviolet curable functional group.
- n in formula (3) is preferably 1 to 1000 mPa s, particularly 1 to 500 mPa s, more preferably 5 to 100 mPa s, especially the viscosity of the organopolysiloxane represented by formula (3) at 25°C. It is preferably 5 to 60 mPa ⁇ s, most preferably 5 to 30 mPa ⁇ s.
- n is preferably 1 to 1000 mPa s, particularly 1 to 500 mPa s, more preferably 5 to 100 mPa s, especially the viscosity of the organopolysiloxane represented by formula (3) at 25°C. It is preferably 5 to 60 mPa ⁇ s, most preferably 5 to 30 mPa ⁇ s.
- the number of silicon atoms per molecule is from 2 to 20, especially from 2 to 5, so that the compound of formula (3) has the desired viscosity.
- the organopolysiloxane of formula (3) can be used alone or as a mixture of two or more.
- the viscosity of the mixture at 25° C. is preferably the viscosity described above.
- the compound of the formula (1) may be an organopolysiloxane represented by the following average unit formula (4).
- each R is independently a group selected from UV-curable functional groups and unsubstituted or fluorine-substituted monovalent hydrocarbon groups, and at least two of all R is a curable functional group, (g+h) is a positive number, e is 0 or a positive number, and f is a number within the range of 0-20.
- UV curable functional groups and monovalent hydrocarbon groups are as defined above for formula (1).
- the preferred viscosities of the organopolysiloxanes of formula (4) are also as specified above for the organopolysiloxanes of formula (1).
- the number of UV-curable functional groups possessed by the organopolysiloxane represented by formula (4) is preferably 2 to 5, more preferably 2 to 4, particularly preferably 2 to 3, and most preferably 2 to 3 per molecule. are two.
- the organopolysiloxane represented by formula (4) preferably has 2 to 20, particularly 2 to 5 silicon atoms per molecule.
- organopolysiloxane having at least two UV-curable functional groups in the molecule represented by the above formula (1), particularly formula (3) or formula (4) include 1,3-bis[ 2-(3,4-epoxycyclohexyl)ethyl]-1,1,3,3-tetramethyldisiloxane, 1,5-bis[2-(3,4-epoxycyclohexyl)ethyl]-1,1,3 , 3,5,5-hexamethyltrisiloxane, 1,1,3,3,5,5,7,7,9,9-decamethyl-1,9-bis[2-(3,4-epoxycyclohexyl) ethyl]pentasiloxane, methyl(tris[2-(3,4-epoxycyclohexyl)ethyl]dimethylsiloxy)silane, tetrakis([2-(3,4-epoxycyclohexyl)ethyl]dimethylsiloxy)ssilane
- each R is independently a group selected from an ultraviolet curable functional group and an unsubstituted or fluorine-substituted monovalent hydrocarbon group, and x is an integer of 3 to 10. , having at least two UV-curable functional groups in the molecule).
- UV-curable functional group and the unsubstituted or fluorine-substituted monovalent hydrocarbon group that can be represented by R in formula (5) are as defined for formula (1) above.
- the preferred viscosity of the organopolysiloxane represented by formula (5) is also as defined above for the organopolysiloxane represented by formula (1).
- a specific example of the cyclic organopolysiloxane having at least two UV-curable functional groups in the molecule represented by formula (5) is 1,3,5-trimethyl-1,3,5-tri[2- (3,4-epoxycyclohexyl)ethyl]cyclotrisiloxane, 1,3,5-trimethyl-1,3,5-tri(3-glycidoxypropyl)cyclotrisiloxane, 1,3,5,7-tetra methyl-1,3,5,7-tetra[2-(3,4-epoxycyclohexyl)ethyl]cyclotetrasiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetra(3 -glycidoxypropyl)cyclotetrasiloxane, 1,3,5,7,9-pentamethyl-1,3,5,7,9-penta[2-(3,4-epoxycyclohexyl)ethyl]cyclopentasiloxane,
- the organopolysiloxanes represented by the above formulas (1) and (3) to (5) can be used singly or optionally in combination of two or more as the component (S1).
- the component (S1) in particular, one or more selected from the group consisting of the organopolysiloxane represented by the above formula (3), the cyclic organopolysiloxane represented by the formula (5), and combinations thereof It is preferred to use organosilicon compounds.
- the viscosity of component (S1) as a whole is preferably 1 to 1000 mPa s, 1 to 500 mPa s, 5 to 100 mPa s, 5 to 60 mPa s, preferably 5 to 30 mPa s at 25°C. ⁇ s.
- Particularly preferred compounds as component (S1) are 1,3-bis[2-(3,4-epoxycyclohexyl)ethyl]-1,1,3,3-tetramethyldisiloxane, 1,5-bis[2- (3,4-epoxycyclohexyl)ethyl]-1,1,3,3,5,5-hexamethyltrisiloxane, 1,1,3,3,5,5,7,7,9,9-decamethyl- 1,9-bis[2-(3,4-epoxycyclohexyl)ethyl]pentasiloxane, methyl (tris[2-(3,4-epoxycyclohexyl)ethyl]dimethylsiloxy)silane, tetrakis ([2-(3, 4-epoxycyclohexyl)ethyl]dimethylsiloxy)silane, 1,3,5,7-tetramethyl-1,3,5,7-tetra[2-(3,4-epoxycyclohexy
- Component (S1-B) Organopolysiloxane and/or organosilane having one UV-curable functional group in one molecule>
- Component (S1-B) is an organosilicon compound having one UV-curable functional group per molecule in the organosilane or organopolysiloxane skeleton, and is mainly a cured product obtained from the composition of the present invention. has the effect of controlling the crosslink density of the composition, adjusting the physical properties of the cured product, and simultaneously reducing the viscosity of the composition. Its molecular structure can be arbitrary as long as it can achieve this purpose.
- the component (S1-B) organosilicon compound is The following average composition formula; R c R′ d SiO (4-cd)/2 (2)
- R is an ultraviolet curable functional group
- R' is a group selected from monovalent hydrocarbon groups, hydroxyl groups, and alkoxy groups, excluding UV-curable functional groups
- c and d are numbers satisfying the following conditions: 1 ⁇ c+d ⁇ 4 and 0.05 ⁇ c/(c+d) ⁇ 0.25, and the number of R in the molecule is one.
- a linear, branched or cyclic organopolysiloxane is a linear, branched or cyclic organopolysiloxane.
- organosilanes and organopolysiloxanes are also collectively referred to as organosilicon compounds hereinafter.
- the UV-curable functional group represented by R in formula (2) is an organic group capable of forming a bond between itself by UV irradiation in the presence or absence of a photoinitiator.
- Examples of UV-curable functional groups include radically polymerizable groups and cationic polymerizable groups.
- the radically polymerizable group is not particularly limited as long as it is a functional group capable of forming a new bond, particularly a bond between radically polymerizable groups, by a radical reaction mechanism. Organic groups containing any group can be mentioned.
- cationic polymerizable groups include groups such as vinyl ether groups, epoxy group-containing groups, and oxetane group-containing groups, such as CH 2 ⁇ CH—O—(CH 2 ) n — (n is an integer of 3 to 20), groups such as glycidyloxy-(CH 2 ) n — (n is an integer from 3 to 20), 3,4-epoxycyclohexyl-(CH 2 ) n — (n is an integer from 2 to 20); be done.
- the UV-curable functional group represented by R in formula (2) is preferably an epoxy group-containing group. Particularly preferred groups are glycidyloxyalkyl groups, especially glycidyloxypropyl groups, epoxycyclohexylalkyl groups, especially 3,4-epoxycyclohexylethyl groups.
- the organosilicon compound represented by the average compositional formula (2) has one UV-curable functional group (R) in one molecule.
- R' in formula (2) is a monovalent hydrocarbon group
- the monovalent hydrocarbon groups are each independently a group consisting of an unsubstituted monovalent hydrocarbon group and a fluorine-substituted monovalent hydrocarbon group. is a group selected from The unsubstituted or fluorine-substituted monovalent hydrocarbon group is preferably a group selected from unsubstituted or fluorine-substituted alkyl, cycloalkyl, arylalkyl, and aryl groups having 1 to 20 carbon atoms. be.
- alkyl group examples include groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, pentyl, and octyl, with the methyl group being particularly preferred.
- cycloalkyl group examples include cyclopentyl and cyclohexyl.
- arylalkyl group examples include benzyl and phenylethyl groups.
- the aryl group examples include a phenyl group and a naphthyl group.
- fluorine-substituted monovalent hydrocarbon groups examples include 3,3,3-trifluoropropyl and 3,3,4,4,5,5,6,6,6-nonafluorohexyl groups. .
- a 3,3,3-trifluoropropyl group is preferred as the fluorine-substituted monovalent hydrocarbon group.
- the organosilicon compound represented by the above formula (2) has a viscosity at 25° C. of 1 to 1000 mPa s, preferably 1 to 500 mPa s, more preferably 1 to 100 mPa s. It is particularly preferred to be up to 50 mPa ⁇ s. By varying the ratio of c and d in formula (2) and the molecular weight, the viscosity of the organosilicon compound can be adjusted.
- the organosilicon compound represented by the above formula (2) is preferably a compound having 1 to 20, preferably 1 to 4 silicon atoms per molecule.
- the organosilicon compound having one UV-curable functional group in one molecule of the component (S1-B) is Formula (3′) below: is an organopolysiloxane compound represented by
- the organopolysiloxane represented by formula (3′) As in the compound represented by formula (2) above, only one of all R 1 to R 8 groups in the organopolysiloxane represented by formula (3′) is a UV-curable functional group. Therefore, the organopolysiloxane represented by Formula (3') has one UV-curable functional group in one molecule.
- the UV-curable functional groups in formula (3′) are bonded between each other by UV irradiation in the presence or absence of a photoinitiator.
- Examples of UV-curable functional groups include radically polymerizable groups and cationic polymerizable groups.
- the radically polymerizable group is not particularly limited as long as it is a functional group capable of forming a new bond, particularly a bond between radically polymerizable groups, by a radical reaction mechanism. Organic groups containing any group can be mentioned.
- cationic polymerizable groups include groups such as vinyl ether groups, epoxy group-containing groups, and oxetane group-containing groups, such as CH 2 ⁇ CH—O—(CH 2 ) n — (n is an integer of 3 to 20), groups such as glycidyloxy-(CH 2 ) n — (n is an integer from 3 to 20), 3,4-epoxycyclohexyl-(CH 2 ) n — (n is an integer from 2 to 20); be done.
- the UV-curable functional groups are preferably one or more epoxy group-containing groups.
- Particularly preferred groups include glycidyloxyalkyl groups such as glycidyloxypropyl groups, epoxycyclohexylalkyl groups, especially 3,4-epoxycyclohexylethyl groups.
- each of R 1 to R 8 other than the UV-curable functional group is independently an unsubstituted or fluorine-substituted monovalent hydrocarbon group, preferably an unsubstituted group having 1 to 20 carbon atoms. or a group selected from fluorine-substituted alkyl, cycloalkyl, arylalkyl, and aryl groups.
- alkyl group include groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, pentyl, and octyl, with the methyl group being particularly preferred.
- Examples of the cycloalkyl group include cyclopentyl and cyclohexyl.
- Examples of the arylalkyl group include benzyl and phenylethyl groups.
- Examples of the aryl group include a phenyl group and a naphthyl group.
- Examples of fluorine-substituted monovalent hydrocarbon groups include 3,3,3-trifluoropropyl and 3,3,4,4,5,5,6,6,6-nonafluorohexyl groups. .
- a 3,3,3-trifluoropropyl group is preferred as the fluorine-substituted monovalent hydrocarbon group.
- n in the formula (3′) is preferably a value such that the viscosity of the organopolysiloxane represented by the formula (3′) at 25° C. is 1 to 1000 mPa s, 1 to 500 mPa s, preferably 1 to 100 mPa. ⁇ s, and particularly preferably 1 to 50 mPa ⁇ s.
- a person skilled in the art can readily determine the value of n so that the viscosity of the organopolysiloxane of formula (3') is within the aforementioned viscosity range without the need for undue trial and error.
- the number of silicon atoms per molecule is preferably 2-20, more preferably 2-5, so that the compound of formula (3') has the desired viscosity.
- the organopolysiloxane of formula (3') can be used alone or as a mixture of two or more.
- the viscosity of the mixture at 25° C. is 1 to 1000 mPa ⁇ s, 1 to 500 mPa ⁇ s, preferably 1 to 100 mPa ⁇ s, more preferably 1 to 50 mPa ⁇ s, Particularly preferably, it is 5 to 20 mPa ⁇ s.
- a specific example of the organopolysiloxane having one UV-curable functional group in the molecule represented by formula (3′) is 1-[2-(3,4-epoxycyclohexyl)ethyl]-1,1 , 3,3,3-pentamethyldisiloxane, 1-[2-(3,4-epoxycyclohexyl)ethyl]-1,1,3,3,5,5,5-heptamethyltrisiloxane, 3-[ 2-(3,4-epoxycyclohexyl)ethyl]-1,1,1,3,5,5,5-heptamethyltrisiloxane and 1-[2-(3,4-epoxycyclohexyl)ethyl]-1 , 1,3,3,5,5,7,7,7-nonamethyltetrasiloxane, 1-(3-glycidoxypropyl)-1,1,3,3,3-pentamethyldisiloxane, 1- (3-glycidoxypropyl)-1,1,3,3,5,
- the organosilicon compound of formula (2) above may also be a cyclic organopolysiloxane represented by formula (5') below.
- formula (5′) each R is independently a group selected from UV-curable functional groups and unsubstituted or fluorine-substituted monovalent hydrocarbon groups, and x is an integer of 3 to 5. , has only one UV-curable functional group in the molecule.
- UV-curable functional group and monovalent hydrocarbon group are as defined for formula (2) above.
- the preferred viscosity of the cyclic organopolysiloxane represented by formula (5') is also as defined above for the organopolysiloxane represented by formula (2). Therefore, the viscosity at 25° C. is preferably 1 to 1000 mPa ⁇ s, more preferably 1 to 500 mPa ⁇ s, more preferably 1 to 100 mPa ⁇ s, particularly preferably 1 to 50 mPa ⁇ s.
- cyclic organopolysiloxane represented by formula (5′) include [2-(3,4-epoxycyclohexyl)ethyl]-pentamethylcyclotrisiloxane, [2-(3,4-epoxycyclohexyl) ethyl]-heptamethylcyclotetrasiloxane, [2-(3,4-epoxycyclohexyl)ethyl]-nonamethylcyclopentasiloxane, 3-glycidoxypropyl-pentamethylcyclotrisiloxane, 3-glycidoxypropyl-hepta methylcyclotetrasiloxane, 3-glycidoxypropyl-nonamethylcyclopentasiloxane.
- component (S1-B) may be an organosilane represented by the following formula (6).
- Formula: RSiR' 3 (6) R is an ultraviolet-curable functional group, and R' is a group selected from monovalent hydrocarbon groups, hydroxyl groups, and alkoxy groups excluding the ultraviolet-curable functional group.
- the UV-curable functional group and the monovalent hydrocarbon group are as defined for formula (2) above, and the alkoxy group has 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 carbon atom. an alkoxy group of ⁇ 3 or a cycloalkyl group of 5 to 20 carbon atoms. Specifically, a methoxy group, an ethoxy group, an isopropoxy group, a cyclopentyl group, or a cyclohexyl group is preferred.
- the preferred viscosity of the organosilane represented by formula (6) is the same as the viscosity defined above for the organopolysiloxane represented by formula (2). Therefore, the viscosity at 25° C. is preferably 1 to 1000 mPa ⁇ s, more preferably 1 to 500 mPa ⁇ s, more preferably 1 to 100 mPa ⁇ s, particularly preferably 1 to 50 mPa ⁇ s.
- organosilane represented by formula (6) include [2-(3,4-epoxycyclohexyl)ethyl]triethylsilane, [2-(3,4-epoxycyclohexyl)ethyl]dimethylphenylsilane, [ 2-(3,4-epoxycyclohexyl)ethyl]dimethyloctylsilane, [2-(3,4-epoxycyclohexyl)ethyl]dimethylcyclohexylsilane, [2-(3,4-epoxycyclohexyl)ethyl]trihexylsilane, [2-(3,4-epoxycyclohexyl)ethyl]tributylsilane, 3-glycidoxypropyltriethylsilane, 3-glycidoxypropyldimethylphenylsilane, 3-glycidoxypropyldimethyloctylsi
- organosilicon compounds represented by the above formulas (2), (3′), (5′), or (6) can be used singly or optionally in combination of two or more. That is, an organosilicon compound represented by formula (2), (3′), (5′), or (6), or a mixture of two or more arbitrarily selected from them, is added to the composition of the present invention. It can be used as component (S1-B).
- an organopolysiloxane represented by formula (3′), a cyclic organopolysiloxane represented by formula (5′), an organosilane represented by formula (6), and any of them It is preferred to use an organosilicon compound selected from a combination of
- the mass ratio of (S1-A) and (S1-B) may be any mass ratio ranging from 100/0 to 0/100 (S1-A/S1-B), but component (S1-A)
- the proportion of component (S1-B) is preferably 10% by mass or more, more preferably 20% by mass or more, and particularly preferably 30% by mass or more, relative to the total amount of 100% by mass of and component (S1-B).
- the following compounds are used as the component (S1-A): 1,3-bis[2-(3,4-epoxycyclohexyl)ethyl]-1,1,3,3-tetramethyldisiloxane, 1,5-bis[2-(3,4-epoxycyclohexyl)ethyl] -1,1,3,3,5,5-hexamethyltrisiloxane, 1,1,3,3,5,5,7,7,9,9-decamethyl-1,9-bis[2-(3 ,4-epoxycyclohexyl)ethyl]pentasiloxane, methyl(tris[2-(3,4-epoxycyclohexyl)ethyl]dimethylsiloxy)silane, tetrakis([2-(3,4-epoxycyclohexyl)ethyl]dimethylsiloxy)
- the mass ratio of this component (S1-A) and component (S1-B) is a value that defines a particularly preferable range, and using only the above component (S1-A), the curable composition of the present invention can also be prepared. Accordingly, the mass ratio of component (S1-B) to component (S1-A) may be from 100/0 to 0/100.
- the curable composition of the present invention is 1,1,1,3,5,5,5-heptamethyl-3-[2-(3,4-epoxycyclohexyl) corresponding to (S1-B) as component (S1). ) Ethyl]trisiloxane, if present, is in the range of 20-100% by weight of the total curable composition, preferably 25-95%, more preferably 30-95%.
- the UV-curable functional group of the component (S1-A) and the ultraviolet light of the component (S1-B) are reactive functional groups of the same type. Therefore, when the UV-curable functional group possessed by component (S1-A) is a radically polymerizable group, the UV-curable functional group possessed by component (S1-B) is also preferably a radically polymerizable group.
- the UV-curable functional group possessed by the component (S1-A) is a cationically polymerizable group
- the UV-curable functional group possessed by the component (S1-B) is also preferably a cationically polymerizable group. It is particularly preferred that both components (S1-A) and (S1-B) have epoxy group-containing groups as UV-curable functional groups.
- component (S1) comprises (S1-1) one or more organopolysiloxanes having an average of two epoxy group-containing groups per molecule, and (S1- 2) one or more organosilicon compounds selected from the group consisting of organopolysiloxanes and/or organosilanes having one epoxy group-containing group per molecule, component (S1-1) and component (S1- 2) in a mass ratio of 100/0 to 0/100 (S1-1/S1-2).
- the organopolysiloxane having an average of two or one epoxy group-containing groups per molecule in this case can be selected from those described above.
- Optional Component (D) A Compound Having One or More UV-Curable Functional Groups in One Molecule and Not Having a Silicon Atom>
- the component (S1) that is, the component (S1-A) and / or the component (S1-B)
- one or more UV-curable functional groups are included in one molecule.
- a compound (component (D)) having silicon atoms and not having silicon atoms may be further added.
- the component (D) in addition to the component (S1-B).
- the UV-curable functional groups possessed by component (D) can be the same as those listed in relation to components (S1), (S1-A), and (S1-B).
- the difference between component (D) and component (S1), component (S1-A), and component (S1-B) is that the latter has a silicon atom in the molecule, whereas component (D) has a It is a point that it does not have a silicon atom inside.
- the chemical structure is not particularly limited, and any compound can be used as component (D) as long as it is a compound that does not contain a silicon atom in the molecule and has one or more UV-curable functional groups described above in the molecule. .
- the component (S1) that is, the component (S1-A) and/or (S1-B) has an ultraviolet-curable reactive group having an epoxy group-containing group that is a cationic polymerizable group
- the component (D) is a molecule
- An organic compound having an epoxy group therein, particularly a compound having an epoxy group and not having a cyclic structure can be used.
- component (D) examples include 2-ethylhexyl glycidyl ether, glycidyl lauryl ether, ethylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, and 1,2-epoxydecane. , 1,2-epoxide decane, and 1,7-octadiene diepoxide, but are not limited thereto. Particularly preferred as component (D) are 1,2-epoxidedecane, 1,7-octadiene diepoxide and 1,4-butanediol diglycidyl ether.
- the viscosity of component (D) at 25° C. is preferably 1 to 1000 mPa ⁇ s, particularly 1 to 500 mPa ⁇ s, more preferably 1 to 100 mPa ⁇ s, particularly preferably 1 to 50 mPa ⁇ s, most preferably 1 to 50 mPa ⁇ s. It is 20 mPa ⁇ s.
- the components (S1-A) and / or (S1-B) when the component (D) is used, the components (S1-A) and (S1-B) contained in the curable composition of the present invention ), and the weight proportion of component (D) to the total amount of component (D) is less than 20%, preferably less than 10%, particularly preferably less than 5%.
- the component (S1) is included as the component (S), or the component (S1) is the main component of the component (S).
- the ratio of component (S1) is preferably 90% by mass or more, more preferably 95% or more, relative to the total mass of the curable composition.
- a photopolymerization initiator can be optionally added in addition to the component (S1).
- the UV-curable functional group of component (S1) is a cationic polymerizable functional group containing an epoxy group-containing group or a vinyl ether group
- a photocationic polymerization initiator is used as the photopolymerization initiator.
- photocationic polymerization initiators compounds capable of generating Bronsted acids or Lewis acids by irradiation with ultraviolet rays or electron beams, so-called photoacid generators, are known. Acids are known to cause reactions between cationically polymerizable functional groups.
- a photoradical polymerization initiator can be used as the photopolymerization initiator.
- the photo-radical polymerization initiator can cure the composition of the present invention by generating free radicals upon irradiation with ultraviolet rays or electron beams, which induce radical polymerization reactions.
- the radically polymerizable initiator will be described later in detail in connection with the embodiment using component (S2) as component (S).
- the UV-curable functional group is a cationically polymerizable functional group, and it is preferable to use a photocationic polymerization initiator. It is particularly preferred to use agents. A polymerization initiator is usually unnecessary when the composition of the present invention is cured by electron beam irradiation.
- photocationic polymerization initiator used in the ultraviolet-curable composition of the present invention can be arbitrarily selected from those known in the art and is not particularly limited. Strong acid-generating compounds such as diazonium salts, sulfonium salts, iodonium salts, and phosphonium salts are known as photocationic polymerization initiators, and these can be used.
- photocationic polymerization initiators include bis(4-tert-butylphenyl)iodonium hexafluorophosphate, cyclopropyldiphenylsulfonium tetrafluoroborate, dimethylphenacylsulfonium tetrafluoroborate, diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroarce diphenyliodonium tetrafluoromethanesulfonate, 2-(3,4-dimethoxystyryl)-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-[2-(furan-2-yl) Vinyl]-4,6-bis(trichloromethyl)-1,3,5-triazine, 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate, 2-[2-(5-methyl)
- the amount of the photocationic polymerization initiator to be added to the ultraviolet curable composition of the present invention is not particularly limited as long as the desired photocuring reaction occurs, but generally the total amount of the ultraviolet curable composition of the present invention It is preferable to use the photocationic polymerization initiator in an amount of 0.1 to 10% by weight, preferably 0.2 to 5% by weight, particularly 0.5 to 4% by weight, based on the
- a photosensitizer can also be used in combination with the photocationic polymerization initiator.
- the use of a sensitizer can increase the photon efficiency of the polymerization reaction, making longer wavelength light available for the polymerization reaction than when only the photoinitiator is used. is known to be particularly effective when the coating thickness of is relatively thick or when relatively long wavelength LED light sources are used.
- Sensitizers include anthracene compounds, phenothiazine compounds, perylene compounds, cyanine compounds, merocyanine compounds, coumarin compounds, benzylidene ketone compounds, (thio)xanthene or (thio)xanthone compounds such as isopropyl Thioxanthone, 2,4-diethylthioxanthone, alkyl-substituted anthracenes, squarium-based compounds, (thia)pyrylium-based compounds, porphyrin-based compounds, etc. are known, and any photosensitizer may be used in the curing of the present invention without being limited to these. can be used in sexual compositions.
- Component (S2) comprises (A) a compound having UV-curable functional groups and having or not having silicon atoms and (B) an organopolysiloxane having no UV-curable functional groups at a ratio of 5:95. It is a mixture containing ⁇ 95:5 (A:B) mass ratio.
- Component (A) A compound having an ultraviolet-curable functional group and having or not having a silicon atom> Component (A) is, therefore, (A1) a compound having a UV-curable functional group and having a silicon atom, (A2) a compound having a UV-curable functional group and having no silicon atom, or (A1) (A2) and in each case the compounds of (A1) and (A2) can each be one or a combination of two or more compounds.
- Component (A1) compound having an ultraviolet-curable functional group and having a silicon atom>
- Component (A1) is a compound having a UV-curable functional group and a silicon atom in its molecule.
- the compound of component (A1) is a compound or two selected from the group consisting of components (S1), (S1-A), (S1-B), (S-1), and (S1-2) described above. It can be a mixture of the above compounds.
- Preferred aspects of component (S1) such as preferred viscosity and preferred number of UV-curable functional groups per molecule, are also preferred for component (A1), except for the type of UV-curable functional group.
- UV-curable functional group of component (A1) examples include a radically polymerizable group and a cationic polymerizable group, but a radically polymerizable group, particularly an acryloxy group, is preferred.
- the compound of component (A1) is preferably organopolysiloxane and/or organosilane having one or more acryloxy groups in one molecule.
- single-end acryloxy-functional polydimethylsiloxane, single-end acryloxy-functional polydimethyldiphenylsiloxane copolymer, both-ends acryloxy-functional polydimethylsiloxane, both-ends acryloxy-functional polydimethyldiphenylsiloxane copolymer, both Trimethylsilyl-terminal polydimethyl(acryloxyalkylmethyl)siloxane copolymers, both-terminal acryloxy-functional polydimethyl(acryloxyalkylmethyl)siloxane copolymers, etc., may be used alone or in combination of two or more. may be used as There are no particular restrictions on its molecular weight and molecular weight distribution, as long as its viscosity falls within the preferred viscosity range described above.
- Component (A2) is a compound having an ultraviolet-curable functional group in its molecule and having no silicon atoms.
- the UV-curable functional groups of component (A2) like the UV-curable functional groups of component (S1), can bond with each other by irradiation with UV rays in the presence or absence of a photoinitiator. It is an organic group that can Examples of UV-curable functional groups include radically polymerizable groups and cationic polymerizable groups, with radically polymerizable groups, particularly acryloxy groups being preferred. Examples of radically polymerizable groups include those described in relation to component (S1). Specifically, compounds having one or more acryloxy groups in one molecule are preferred.
- the molecular structure is not limited as long as the object of the present invention can be achieved, and may be linear, branched, cyclic, cage-like, or the like.
- the component (A2) has a viscosity at 25°C of 1 to 1000 mPa ⁇ s, particularly 1 to 500 mPa ⁇ s. s, more preferably 1 to 100 mPa ⁇ s, particularly preferably 1 to 20 mPa ⁇ s, and most preferably 1 to 10 mPa ⁇ s.
- the above component (A2) is preferably a compound containing 1 to 4, preferably 1 to 3, more preferably 1 to 2 acryloxy groups per molecule.
- a compound having a plurality of acryloxy groups there are no restrictions on the position of the acryloxy groups in the molecule, and they may be located close to each other or apart from each other.
- the component (A2) may be a single compound having one acryloxy group, or a mixture of two or more compounds having one acryloxy group.
- the component (A2) may be a mixture of one or more compounds having one acryloxy group and one or more compounds having two or more acryloxy groups.
- compounds having one acryloxy group include isoamyl acrylate, octyl acrylate, lauryl acrylate, stearyl acrylate, diethylene glycol monoethyl ether acrylate, diethylene glycol monomethyl ether acrylate, 2-ethylhexyl acrylate, phenoxyethyl acrylate, and diethylene glycol monophenyl ether acrylate.
- the compound having one acryloxy group can be used alone or in combination of two or more, taking into account the viscosity, curability, hardness and glass transition temperature of the composition after curing. Among them, it is preferable to use one or a combination of two or more compounds selected from 2-ethylhexyl acrylate, isobornyl acrylate, and dicyclopentanyl acrylate.
- compounds having two or more acryloxy groups include diethylene glycol diacrylate, triethylene glycol diacrylate, neopentyl glycol diacrylate, polyethylene glycol diacrylate, 1,4-bis(acryloyloxy)butane, 1,6- Bis(acryloyloxy)hexane, 1,9-bis(acryloyloxy)nonane, trimethylolpropane triacrylate, tris(2-acryloyloxy)ethylisosialate, and pentaerythritol tetraacrylate.
- component (A1) and component (A2) can be used, or both can be used in combination.
- components (A1) and (A2) are used in combination, and when it is a combination of a compound having two or more acryloxy groups and a compound having one acryloxy group, they can be combined in any ratio.
- [compound having two or more acryloxy groups]/[compound having one acryloxy group] is preferably in the range of 1/99 to 50/50 (mass ratio).
- component (A2) is used as component (A), which is combined with component (B) to form component (S) of the curable composition of the present invention.
- Component (B) is an organopolysiloxane having no UV-curable functional groups.
- Component (B) is particularly preferably one or more alkenyl group-containing organopolysiloxanes selected from (B1) and (B2) below.
- (B1) an organopolysiloxane having 3 or more alkenyl groups in one molecule and no UV-curable functional group;
- (B2) Organopolysiloxane having two or more alkenyl groups per molecule, a vinyl group content of 5% by mass or more, and no UV-curable functional groups.
- the alkenyl group is a terminal alkenyl group.
- the vinyl group content refers to the ratio of the mass of the vinyl group portion (CH 2 ⁇ CH—) of all alkenyl groups contained in the compound to the mass of the entire molecule.
- the above component (B) has the following average composition formula: R a R′ b SiO (4-ab)/2 (7)
- R is an alkenyl group
- R' is a group selected from monovalent hydrocarbon groups excluding alkenyl groups, hydroxyl groups, and alkoxy groups
- a and b are numbers satisfying the following conditions: 1 ⁇ a+b ⁇ 3 and 0.1 ⁇ a/(a+b) ⁇ 1.0, and have at least two alkenyl groups (R) in the molecule.
- It can be a linear, branched or cyclic alkenyl group-containing organopolysiloxane represented by.
- the linear, branched, or cyclic organopolysiloxane represented by the average compositional formula (7) has at least two alkenyl groups (R) on average per molecule, but alkenyl
- the average number of groups per molecule is preferably 3 to 10, more preferably 3 to 8, particularly preferably 4 to 8.
- alkenyl groups represented by R in formula (7) include alkenyl groups having 2 to 8 carbon atoms, particularly alkenyl groups having a terminal double bond, specifically vinyl, allyl, butenyl, and pentenyl groups. , hexenyl groups, and octenyl groups. Among them, a hexenyl group is particularly preferred.
- R' in formula (7) is a group selected from monovalent hydrocarbon groups other than alkenyl groups, hydroxyl groups, and alkoxy groups, excluding alkenyl groups. Hydrocarbon groups and fluorine-substituted monovalent hydrocarbon groups are included.
- the unsubstituted or fluorine-substituted monovalent hydrocarbon group is preferably a group selected from unsubstituted or fluorine-substituted alkyl, cycloalkyl, arylalkyl, and aryl groups having 1 to 20 carbon atoms. be.
- alkyl group examples include groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, pentyl, hexyl and octyl, with methyl and hexyl being particularly preferred.
- cycloalkyl group examples include cyclopentyl and cyclohexyl.
- arylalkyl group examples include benzyl and phenylethyl groups. Examples of the aryl group include a phenyl group and a naphthyl group.
- fluorine-substituted monovalent hydrocarbon groups examples include 3,3,3-trifluoropropyl and 3,3,4,4,5,5,6,6,6-nonafluorohexyl groups. .
- a 3,3,3-trifluoropropyl group is preferred as the fluorine-substituted monovalent hydrocarbon group.
- the organopolysiloxane represented by the above formula (7) has a viscosity at 25°C of 1 to 1000 mPa ⁇ s, preferably 5 to 500 mPa ⁇ s, most preferably 5 to 200 mPa ⁇ s.
- the viscosity of the organopolysiloxane can be adjusted by varying the ratio of a and b in formula (1) and the molecular weight.
- the organopolysiloxane represented by formula (7) preferably has an average of 3 to 50, more preferably 4 to 20, and particularly preferably 4 to 10 silicon atoms per molecule.
- component (B) organopolysiloxane is Formula (8) below: It is a compound represented by
- the organopolysiloxane represented by formula (8) has an average of two or more alkenyl groups per molecule.
- an average of two or more per molecule are alkenyl groups.
- the structure of the alkenyl group is not limited to a specific chemical structure as long as it has a carbon-carbon double bond.
- the alkenyl group is particularly preferably a terminal alkenyl group, such as vinyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, and 4-vinyl.
- alkenyl groups having 2 to 20 carbon atoms such as phenyl groups.
- the alkenyl-containing group is preferably a group selected from vinyl group, allyl group, hexenyl group and octenyl group, and particularly preferably allyl group and hexenyl group.
- R 1 to R 8 are not UV-curable functional groups, but are each independently unsubstituted or fluorine-substituted monovalent hydrocarbon groups, preferably non-hydrocarbon groups having 1 to 20 carbon atoms.
- the alkyl group include groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, pentyl, and octyl, with the methyl group being particularly preferred.
- Examples of the cycloalkyl group include cyclopentyl and cyclohexyl.
- Examples of the arylalkyl group include benzyl and phenylethyl groups.
- Examples of the aryl group include a phenyl group and a naphthyl group.
- Examples of fluorine-substituted monovalent hydrocarbon groups include 3,3,3-trifluoropropyl and 3,3,4,4,5,5,6,6,6-nonafluorohexyl groups. .
- a 3,3,3-trifluoropropyl group is preferred as the fluorine-substituted monovalent hydrocarbon group.
- n in formula (8) is preferably 1 to 1000 mPa s, more preferably 5 to 500 mPa s, particularly preferably 5 to 100 mPa s, at 25° C. for the organopolysiloxane represented by formula (8). is a value that becomes One of ordinary skill in the art can readily determine the value of n so that the viscosity of the organopolysiloxane of formula (8) is within the viscosity range described above, without the need for undue trial and error. However, in general, it is preferred that the number of silicon atoms per molecule is 3-150, especially 3-50, so that the compound of formula (8) has the desired viscosity.
- the number of alkenyl groups possessed by the organopolysiloxane of formula (8), which is the component (B), is preferably 2 to 10, more preferably 3 to 10, particularly preferably 3 to 8, on average per molecule as a whole. Most preferably 4-8.
- the number of alkenyl groups is two, it is necessary to control the above number of n so that the vinyl group content is 5% by mass or more.
- the specific value of n at that time is 12 or less.
- the organopolysiloxane of formula (8) can be used singly or as a mixture of two or more.
- the viscosity of the mixture at 25° C. is preferably the viscosity described above.
- the compound of the average composition formula (7) may be a branched organopolysiloxane represented by the following average unit formula (9).
- each R is independently a group selected from an alkenyl group and an unsubstituted or fluorine-substituted monovalent hydrocarbon group, and at least two of all R are alkenyl groups.
- (g+h) is a positive number
- e is 0 or a positive number
- f is a number within the range of 0-100.
- the alkenyl group and monovalent hydrocarbon group are as defined for formula (7) above.
- the preferred viscosities of the organopolysiloxanes of formula (9) are also as specified above for the organopolysiloxanes of formula (7).
- alkoxy groups and silanol groups may remain in the molecule as long as the objects and effects of the present invention are not impaired.
- the organopolysiloxane represented by formula (9) preferably has 4 to 30, particularly 6 to 20 silicon atoms per molecule.
- the number of alkenyl groups possessed by the organopolysiloxane represented by the formula (9) is preferably 2 to 10, more preferably 3 to 10, particularly preferably 3 to 8, and most preferably 3 to 8 on average per molecule as a whole. 4-8.
- the number of alkenyl groups is two, it is necessary to control the number of silicon atoms and the number of substituents thereof, and design the molecule so that the vinyl group content is 5% by mass or more. .
- the organopolysiloxane of formula (9) is a branched organopolysiloxane having (RSiO 3/2 ) units.
- linear organopolysiloxane represented by (7) above, particularly formula (8) include both-end dimethylvinylsilylpolydimethylsiloxane, both-end dimethylvinylsilylpolydimethyl/diphenylsiloxane copolymer, both dimethylvinylsilyl-terminated polymethylphenylsiloxane, both-terminated dimethylhexenylsilylpolydimethylsiloxane, both-terminated trimethylsilylpolydimethyl/methylvinylsiloxane copolymer, both-terminated dimethylvinylsilylpolydimethyl/methylvinylsiloxane copolymer, both-terminated trimethylsilylpoly Dimethyl/methylhexenylsiloxane copolymer, both-terminated dimethylvinylsilylpolydimethyl/methylhexenylsiloxane copolymer, both-terminated
- branched organopolysiloxane represented by (7) above, particularly formula (9) include a polysiloxane composed of M Vi (dimethylvinylsiloxy) units and T (methylsiloxy) units, M Vi units and Q Polysiloxane consisting of (siloxy) units, M Polysiloxane consisting of Vi units, M (trimethylsilyl) units and Q units, Polysiloxane consisting of M Vi units, D (dimethylsiloxy) units and T units, M Vi units and M units and T units, polysiloxane composed of M Vi units and T Ph (phenylsiloxy) units, polysiloxane composed of M Vi units, M units and T Ph units, M Vi units, D units and T Ph units polysiloxane consisting of M Hex (dimethylhexenylsiloxy) units and T units, polysiloxane consisting of M Hex units and Q units, polysiloxane consisting of M
- the alkenyl group-containing branched organopolysiloxane represented by the above formula (7) or (9) is particularly preferably an alkenyl group-containing silsesquioxane, the alkenyl group of which is a C2-10 alkenyl group, preferably a C2 ⁇ 10 terminal alkenyl groups, particularly preferably hexenyl groups.
- each R is independently a group selected from an alkenyl group and an unsubstituted or fluorine-substituted monovalent hydrocarbon group, x is an integer of 3 to 10, and in the molecule having at least two alkenyl groups in).
- alkenyl group and the unsubstituted or fluorine-substituted monovalent hydrocarbon group that can be represented by R in formula (10) are as defined for formula (7) above.
- the preferred viscosity of the organopolysiloxane represented by formula (10) is as defined above for the organopolysiloxane represented by formula (7).
- cyclic organopolysiloxane represented by formula (10) include 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane and 1,3,5-trimethyl -1,3,5-trihexenylcyclotrisiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetrahexenylcyclotetrasiloxane, 1,3,5,7,9-pentamethyl- 1,3,5,7,9-pentavinylcyclopentasiloxane and 1,3,5,7,9-pentamethyl-1,3,5,7,9-pentahexenylcyclopentasiloxane.
- the organopolysiloxanes represented by formulas (7) and (8) to (10) can be used singly or in combination of two or more as component (B).
- Component (B) is particularly one or more selected from the group consisting of the organopolysiloxane represented by the above formula (8), the branched organopolysiloxane represented by formula (9), and combinations thereof. It is preferred to use an organopolysiloxane of
- Compounds recommended as component (B) are both-terminated trimethylsilylpolydimethyl/methylhexenylsiloxane copolymer, both-terminated dimethylvinylsilylpolydimethyl/methylhexenylsiloxane copolymer, and both-terminated dimethylhexenylsilylpolydimethyl/methylhexenylsiloxane.
- Copolymer double-ended trimethylsilylpolymethylhexenylsiloxane, double-ended silanol polymethylhexenylsiloxane, polysiloxane consisting of M units, D Hex units and T units, polysiloxane consisting of M units, D Hex units and T Ph units, M Polysiloxane consisting of Hex units and T Ph units Polysiloxane consisting of M Hex units, D units and T Ph units Polysiloxane consisting of M units and T Hex units Polysiloxane consisting of D units and T Hex units T Hex It is one compound or a combination of two or more compounds selected from the group consisting of polysiloxanes consisting of units.
- polysiloxanes composed of M units, D 2 Hex units and T 2 Ph units, polysiloxanes composed of D 2 Hex units and T 3 Ph units, and polysiloxanes composed of T 2 Hex units are particularly preferably used.
- component (S2) of the present invention is a mixture containing component (A) and component (B) described above in a weight ratio of 5:95 to 95:5 (A:B). That is, the mixing ratio of component (A) and component (B) is that the total amount of component (A) and component (B) is 100% by mass, the ratio of component (A) is 5 to 95% by mass, and the ratio of component (B) is 5 to 95% by mass. is 95 to 5% by mass.
- the ratio of components (A) and (B) is within this range, the viscosity of the curable composition is adjusted appropriately, good UV curability is maintained, and the mechanical properties of the resulting cured product, particularly tensile elongation, are improved.
- a preferable proportion of component (A) is 15% by mass or more and 85% by mass or less, more preferably 20% by mass or more and 80% by mass or less, and still more preferably 25% by mass of the total amount of components (A) and (B). Above, 75 mass % or less.
- ⁇ Optional component when using component (S2)> When the above components (A) and (B) are used as the component (S) of the ultraviolet curable composition of the present invention, in addition to the components (A) and (B), a photopolymerization initiator is optionally added. be able to.
- the UV-curable functional group possessed by the component (A) is a cationic polymerizable functional group
- the UV-curable functional group described in connection with the embodiment using the component (S1) as the component (S) of the present invention is It is preferable to use a photocationic polymerization initiator that can be used in the case of a cationic polymerizable functional group.
- the above-described description of the photocationically polymerizable initiator can be applied as it is.
- the ultraviolet curable functional group which the component (A) has is a radically polymerizable group
- a photoradical polymerization initiator together with the component (A)
- free radicals are generated by irradiation with ultraviolet rays or electron beams, which can cause radical polymerization reaction to cure the composition of the present invention.
- a polymerization initiator is usually unnecessary when the composition of the present invention is cured by electron beam irradiation.
- Radical photopolymerization initiators are roughly classified into photocleavage type and hydrogen abstraction type, but the photoradical polymerization initiator used in the composition of the present invention is arbitrarily selected from those known in the art. It can be selected and used, and is not particularly limited to a specific one.
- photoradical polymerization initiators include acetophenone, p-anisyl, benzyl, benzoin, benzophenone, 2-benzoylbenzoic acid, 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(dimethylamino)benzophenone.
- benzoin methyl ether benzoin isopropyl ether, benzoin isobutyl ether, benzoin ethyl ether, 4-benzoylbenzoic acid, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl-1, 2'-biimidazole, methyl 2-benzoylbenzoate, 2-(1,3-benzodioxol-5-yl)-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-benzyl -2-(dimethylamino)-4'-morpholinobtyrophenone, ( ⁇ )-camphorquinone, 2-chlorothioxanthone, 4,4'-dichlorobenzophenone, 2,2-diethoxyacetophenone, 2,2-dimethoxy-2- Phenylacetophenone, 2,4-diethylthioxanthene-9-one, diphenyl(
- Omnirad registered trademark
- 651, 184, 1173, 2959, 127, 907, 369, 369E, and 379EG alkylphenone photopolymerization initiator, IGM Resins B.V.
- Omnirad registered trademark
- TPO H acylphosphine oxide photoinitiator
- IGM RESINS B.V. Omnirad (registered trademark) MBF and 754 (intramolecular hydrogen abstraction type photoinitiator IGM Resins B.V.), Irgacure® OXE01 and OXE02 (oxime ester-based non-social polymerization initiators, BASF).
- the amount of the radical photopolymerization initiator to be added to the curable composition of the present invention is not particularly limited as long as the desired photopolymerization reaction or photocuring reaction occurs. It is used in an amount of 0.01 to 5% by weight, preferably 0.05 to 1% by weight.
- a photosensitizer can also be used in combination with the photoradical polymerization initiator.
- the use of a sensitizer can be expected to have the effect of increasing the photon efficiency of the polymerization reaction, as in the case of using the photocationic polymerization initiator.
- the photosensitizer the above-described photosensitizers that can be used in combination with the photocationic polymerization initiator are exemplified and can be preferably used.
- Component (S) of the curable composition of the present invention consists of one or more components selected from component (S1) or one or more components selected from component (S2). That is, the component (S) consists of only the component (S1) or only the component (S2).
- component (S) consists of component (S1), and the number of UV-curable functional groups in component (S1) is two per molecule on average.
- Component (S) consists of component (S1), and component (S1) is an organopolysiloxane having one UV-curable functional group in its molecule.
- Component (S) consists of Component (S1), and the UV-curable functional group possessed by Component (S1) is an acryloxy group-containing group, a methacryloxy group-containing group, an epoxy group-containing group, or an oxetane group-containing group. , and vinyl ether group-containing groups.
- component (S) consists of component (S2), and the UV-curable functional group possessed by component (A) in component (S2) is an acryloxy group-containing group, a methacryloxy group-containing group, an epoxy group-containing group, or an oxetane; It is a functional group selected from the group consisting of a group-containing group and a vinyl ether group-containing group.
- Component (S) consists of component (S1), and the UV-curable functional group of component (S1) is an epoxy group-containing group.
- component (S1) consists solely of epoxy-functional organopolysiloxanes or comprises epoxy-functional organopolysiloxanes.
- the component (S) consists of the component (S2), and the component (A) of the component (S2) has an acryloxy group as an ultraviolet-curable functional group and a silicon atom and/or a compound and/or an ultraviolet-curable functional group. is a compound having an acryloxy group and no silicon atom.
- the component (S) consists of the component (S2), and the component (A) of the component (S2) has an acryloxy group as an ultraviolet-curable functional group and a silicon atom and/or a compound and/or an ultraviolet-curable functional group. is a compound having an acryloxy group and no silicon atom, and component (B) is an organopolysiloxane having an alkenyl group.
- component (A) is more preferably a silicon-free compound.
- Component (S) consists of component (S2), and component (A) of component (S2) is a compound or a mixture of two or more compounds having one acryloxy group as a UV-curable group.
- the component (S) consists of the component (S2), and the component (A) of the component (S2) comprises one or more compounds having one acryloxy group as an ultraviolet-curing group and one or more compounds having two or more acryloxy groups as UV-curable groups.
- Component (S) is a mixture with a compound of (9)
- Component (S) consists of component (S2), and component (A) of component (S2) is a compound having one or more acryloxy groups as UV-curable groups and no silicon atoms.
- Component (S) consists of Component (S2), and Component (B) of Component (S2) is an organopolysiloxane having (RSiO 3/2 ) units, or has (RSiO 3/2 ) units. Contains organopolysiloxane.
- component (B) is preferably an alkenyl group-containing silsesquioxane.
- the component (S) consists of the component (S2), and the component (B) of the component (S2) is an organopolysiloxane having 3 or more alkenyl groups per molecule, or 3 Includes organopolysiloxanes with one or more alkenyl groups.
- component (B) is preferably an alkenyl group-containing silsesquioxane.
- Component (S) consists of component (S2), component (B) of component (S2) is an organopolysiloxane having an alkenyl group, and the alkenyl group is an alkenyl group having 3 to 8 carbon atoms.
- the amount of component (S) is 90 to 99.99 parts by mass, preferably 93 to 99.99 parts by mass, and 95 to 99 parts by mass with respect to 100 parts by mass in total with component (C) described below. More preferably, it is 0.99 parts by mass.
- the total amount of component (S) and component (C) is preferably 95 to 100 parts by mass, more preferably 97 to 100 parts by mass, relative to the total mass of the ultraviolet curable composition.
- the UV-absorbing compound of component (C) of the present invention is a component that absorbs UV rays in the cured product obtained from the UV-curable composition and provides an effective UV shielding effect.
- UV-absorbing compounds are well-known compounds in the art, and many types of UV-absorbing compounds are commercially available as so-called UV absorbers. It is preferred to use a UV-absorbing compound that has good miscibility with component (S) in the UV-curable composition of the present invention.
- the type and amount of component (C) added is such that a cured product having a thickness of 10 ⁇ m obtained by curing the ultraviolet curable composition of the present invention exhibits a light transmittance of 98% or more at a visible light wavelength of 450 nm. can be adjusted.
- a good ultraviolet shielding effect can be exhibited, and the lowest light transmittance of the cured product in this wavelength range can be 50% or less.
- the chemical structure of the UV-absorbing compound of component (C) is not limited, but compounds having a maximum absorption wavelength in the wavelength range of 340 to 420 nm are preferred.
- UV-absorbing compound of component (C) examples include triazine-based compounds, benzotriazole-based compounds, benzophenone-based compounds, oxybenzophenone-based compounds, salicylic acid ester-based compounds, cyanoacrylate-based compounds, and amino-substituted pyrimidine-based compounds. These can be used singly or in combination of two or more. Among these, heterocyclic compounds having nitrogen atoms, that is, triazine-based compounds, benzotriazole-based compounds, and amino-substituted pyrimidine-based compounds can be preferably used.
- component (C) examples include 2,4-bis-[ ⁇ 4-(4-ethylhexyloxy)-4-hydroxy ⁇ -phenyl]-6-(4-methoxyphenyl)-1,3,5- Triazine (Tinosorb S, manufactured by BASF), hydroxyphenyl-s-triazine (TINUVIN (registered trademark) 477, manufactured by BASF), 2,4-bis[2-hydroxy-4-butoxyphenyl]-6-(2,4- Dibutoxyphenyl)-1,3,5-triazine (TINUVIN® 460, manufactured by BASF), 2-(4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine-2 -yl)-5-hydroxyphenyl and [(C10-C16 (mainly C12-C13) alkyloxy) methyl] oxirane (TINUVIN® 400, manufactured by BASF), 2-[4,6- bis(2,4-dimethylphenyl)-1,3,5-triazine
- amino-substituted pyrimidine compounds such as FDB-009 (manufactured by Yamada Kagaku Kogyo Co., Ltd.) can also be preferably used as the component (C) UV-absorbing compound.
- the maximum absorption wavelength of component (C) is preferably present in the wavelength range of 340 to 420 nm, more preferably in the wavelength range of 350 to 405 nm.
- the maximum absorption wavelength means the absorption maximum wavelength showing the maximum absorbance among a plurality of absorption maxima in the ultraviolet/visible spectral absorption spectrum with a measurement range of 300 nm to 800 nm.
- Component (C) may be used alone or in combination of two or more. It is 0.01 to 10 parts by mass. It is preferably 0.1 to 8 parts by mass, more preferably 1 to 6 parts by mass.
- the amount of the UV-absorbing compound By setting the amount of the UV-absorbing compound to be within the above range, the UV-shielding function of the cured product layer can be sufficiently exhibited, and the UV-absorbing compound allows the curable composition having a thickness of 10 ⁇ m to be UV-cured. UV curing can be done quickly enough.
- the cured product obtained from the ultraviolet curable composition of the present invention has a good ultraviolet shielding function in the wavelength range of 360 to 405 nm, but has the lowest light transmission in the measurement range of the ultraviolet/visible spectral absorption spectrum of 300 nm to 800 nm. It is preferable that the wavelength range indicating the index is 385 to 400 nm. That is, the cured product of the present invention preferably has the greatest UV shielding effect in the wavelength range of 385 to 400 nm in the measurement range of 300 nm to 800 nm.
- the lowest light transmittance in the wavelength range of 360 to 405 nm for a sample with a thickness of 10 ⁇ m is 50% or less. More preferably, however, the light transmittance value is 25% or less, and even more preferably 10% or less.
- the value of the light transmittance can be adjusted by selecting the type of ultraviolet absorbing compound used as the component (C) and optimizing the amount added to the curable composition, while considering the ultraviolet curability of the composition. be.
- the cured product obtained from the curable composition of the present invention includes the molecular chain lengths of component (S1) and component (A), the position of the UV-curable functional group in the molecule, the molecular structure, and the structure and structure of component (B).
- S1 and component (A) the molecular chain lengths of component (S1) and component (A)
- the position of the UV-curable functional group in the molecule the molecular structure
- component (B) the structure and structure of component (B).
- the desired physical properties of the cured product and the curing rate of the curable composition can be obtained, and the viscosity of the curable composition is the desired value.
- a cured product obtained by curing the curable composition of the present invention is also included in the scope of the present invention.
- the shape of the cured product obtained from the composition of the present invention is not particularly limited.
- the cured product obtained from the composition of the present invention is particularly preferably in the form of a thin coating layer, particularly preferably an insulating coating layer.
- the curable composition of the present invention is suitable for use as a coating agent or potting agent, particularly as an insulating coating agent or potting agent for electronic devices and electrical devices.
- the cured product obtained by curing the curable composition of the present invention is characterized by being optically transparent in the visible light region and having a large ultraviolet shielding effect.
- a cured product with a thickness of 10 ⁇ m obtained from the curable composition of the present invention has a transmittance of 98% or more at a wavelength of 450 nm and a light transmittance of 50% or less at least at one point in the wavelength range of 360 to 405 nm. It is possible to reduce the value to 10% or less.
- the cured product obtained from the curable composition of the present invention is excellent in mechanical properties, particularly tensile properties. When evaluated at 25° C.
- the curable composition of the present invention is useful as a layer-forming material for flexible displays.
- the cured product obtained by curing the curable composition of the present invention can be designed to have a dielectric constant of less than 3.0, less than 2.8, etc.
- Chemical compositions can also be used to form coating layers with low dielectric constants.
- the viscosity of the entire composition must be E It is preferably 500 mPa ⁇ s or less at 25° C. when measured using a type viscometer.
- a preferable viscosity range is 5 to 100 mPa ⁇ s, more preferably 5 to 60 mPa ⁇ s, particularly preferably 5 to 30 mPa ⁇ s, and most preferably 5 to 20 mPa ⁇ s.
- compounds having preferable viscosities can be used as respective components so that the viscosity of the entire composition has the desired viscosity.
- the curable composition of the present invention can achieve a viscosity suitable for the above-described coating agent by using each of the components described above, without substantially using an organic solvent.
- the curable composition is substantially free of organic solvents.
- substantially free of organic solvent means that the content of organic solvent is less than 0.05% by mass of the total composition, and is preferably analyzed using an analytical method such as gas chromatography. It means that it is below the limit.
- Component (E) To improve the wettability of the composition to the substrate and form a defect-free coating film when the ultraviolet curable composition of the present invention is applied as a coating agent to the surface of the substrate using any method.
- a component (E) selected from the following can be added to the composition of the present invention containing the components described above. It is particularly preferred to use an inkjet printing method as a method for coating a substrate with the composition of the invention.
- component (E) is a component that improves the wettability of the ultraviolet-curable organopolysiloxane composition of the present invention to substrates, and particularly significantly improves ink jet printing properties.
- Component (E) is at least one compound selected from the group consisting of (E1), (E2) and (E3) below.
- Component (E1) is a silicon-free non-acrylic non-ionic surfactant, ie a non-acrylic non-ionic surfactant.
- a non-acrylic surfactant means that the surfactant does not have a (meth)acrylate group in its molecule.
- Surfactants that can be used as component (E1) include organic nonionic surfactants such as glycerin fatty acid esters, sorbitan fatty acid esters, polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, alkyl glycosides, and acetylene glycol polyethers.
- Active agents, fluorine-based nonionic surfactants, and the like can be mentioned, and these can be used alone or in combination of two or more.
- Specific examples of the component (E1) include, as organic nonionic surfactants, Emulgen series and Rheodor series manufactured by Kao Corporation, Surfynol 400 series manufactured by Evonik Industries, and Olphine E series manufactured by Nissin Chemical Industry Co., Ltd.
- Fluorinated nonionic surfactants include FC-4400 series manufactured by 3M and Megafac 550 and 560 series manufactured by DIC Corporation. Among these, Surfynol 400 series and Olphine E series, which are alkynol polyethers, are particularly preferred.
- Component (E2) is a nonionic surfactant containing silicon atoms and having an HLB value of 4 or less.
- the HLB value is a value that represents the degree of affinity of a surfactant for water and an organic compound. /molecular weight) is used.
- Silicone polyethers having polyethers as hydrophilic moieties, glycerol silicones having (di)glycerol derivatives as hydrophilic moieties, and carbinol silicones having hydroxyethoxy groups as hydrophilic moieties are known as silicon-containing nonionic surfactants. .
- surfactants those with an HLB value of 4 or less, that is, those with a hydrophilic moiety mass fraction of 20% by mass or less, are preferably used in the composition of the present invention.
- carbinol silicone is particularly preferred.
- Component (E3) is a silicone oil having a viscosity of 90 mPa ⁇ s or less at 25°C.
- silicone oils include both-terminated trimethylsilyl-polydimethylsiloxane, both-terminated dimethylvinylsilyl-polydimethylsiloxane, both-terminated trimethylsilyl-dimethylsiloxy/methylvinylsiloxy copolymer, both-terminated dimethylvinylsilyl-dimethylsiloxy/methylvinylsiloxy copolymer.
- a preferable viscosity range of the silicone oil is 2 to 50 mPa ⁇ s, a more preferable range is 2 to 30 mPa ⁇ s, and a further preferable viscosity range is 5 to 20 mPa ⁇ s.
- the value of the viscosity here is the value measured at 25° C. using the rotational viscometer described in the Examples.
- the above-mentioned components (E1) to (E3) can use one or a combination of two or more thereof.
- the amount of component (E) to be added to the curable composition is not particularly limited, but the total amount of component (S1), component (A), component (B), component (C), and component (D) described above. is 100% by mass, and the total amount of components (E1) to (E3) (collectively referred to as component (E)) is preferably 0.05% by mass or more and 1% by mass or less. .
- the amount of component (E) is less than 0.05% by mass with respect to 100% by mass of the total amount of component (S1), component (A), component (B), component (C), and component (D) ,
- the effect of improving the wettability of the curable composition to the substrate may not be sufficiently obtained. This is because component (E) may bleed out from the cured product after curing.
- the silicone oil of the component (E3) can be used alone, or the component (E3) can be used in combination with one or more components selected from the group consisting of the components (E1) and (E2). It is particularly preferred to use component (E3) alone as component (E).
- additives include, but are not limited to, the following.
- Adhesion imparting agent Adhesion promoters can be added to the composition of the present invention to improve adhesion and adhesion to substrates in contact with the composition.
- an adhesion-imparting agent may be added to the curable composition of the present invention. is preferred. Any known adhesion promoter can be used as the adhesion promoter as long as it does not inhibit the curing reaction of the composition of the present invention.
- adhesion promoters examples include trialkoxysiloxy groups (e.g., trimethoxysiloxy group, triethoxysiloxy group) or trialkoxysilylalkyl groups (e.g., trimethoxysilylethyl group, triethoxysilylethyl group) and a hydrosilyl group or an alkenyl group (e.g., vinyl group, allyl group), or an organosiloxane oligomer having a linear, branched or cyclic structure with about 4 to 20 silicon atoms; trialkoxy Organosilanes having a siloxy group or a trialkoxysilylalkyl group and a methacryloxyalkyl group (e.g., 3-methacryloxypropyl group), or organosilanes having a linear, branched or cyclic structure having about 4 to 20 silicon atoms Siloxane oligomer; trialkoxysiloxy group
- the amount of the adhesion promoter added to the curable composition of the present invention is not particularly limited.
- Additives may be added to the composition of the present invention in addition to or instead of the adhesion imparting agent described above.
- Additives that can be used include leveling agents, silane coupling agents that are not included in the adhesiveness imparting agents described above, ultraviolet absorbers, antioxidants, polymerization inhibitors, fillers (reinforcing fillers, insulating and functional fillers such as thermally conductive fillers). Suitable additives can be added to the composition of the present invention, if desired. Further, a thixotropic agent may be added to the composition of the present invention as necessary, particularly when used as a potting agent or sealing material.
- the UV-curable composition of the present invention can be cured not only by ultraviolet rays but also by electron beams, which is also an aspect of the present invention.
- the curable composition of the present invention has a low viscosity and is particularly useful as a material for forming insulating layers that constitute various articles, especially electronic devices and electrical devices.
- the composition of the present invention is coated on a substrate, or sandwiched between two substrates, at least one of which is made of a material that transmits ultraviolet rays or electron beams, and is irradiated with ultraviolet rays or electron beams.
- the material can be cured to form an insulating layer.
- the composition of the present invention can be patterned when applied to a substrate and then cured, or the composition can be applied to a substrate and cured with UV or electron beam radiation.
- the stiffening layer according to the present invention is an insulating layer, it can be designed to have a low dielectric constant of less than 3.0.
- the curable composition of the present invention is particularly suitable as a material for forming insulating layers of display devices such as touch panels and displays because the cured product obtained therefrom has good transparency.
- the insulating layer may form any desired pattern, as described above, if desired.
- a display device such as a touch panel and a display including an insulating layer obtained by curing the ultraviolet-curable organopolysiloxane composition of the present invention is also an aspect of the present invention.
- the curable composition of the present invention can be used to coat an article and then cured to form an insulating coating layer (insulating film). Therefore, the composition of the present invention can be used as an insulating coating agent. A cured product formed by curing the curable composition of the present invention can also be used as an insulating coating layer.
- the insulating film formed from the curable composition of the present invention can be used for various purposes. In particular, it can be used as a component of electronic devices or as a material used in the process of manufacturing electronic devices. Electronic devices include electronic equipment such as semiconductor devices and magnetic recording heads.
- the curable composition of the present invention can be used for semiconductor devices such as LSI, system LSI, DRAM, SDRAM, RDRAM, D-RDRAM, insulating films for multi-chip module multilayer wiring boards, interlayer insulating films for semiconductors, and etching stopper films. , a surface protective film, a buffer coat film, a passivation film in LSI, a cover coat for flexible copper-clad plates, a solder resist film, and a surface protective film for optical devices.
- the UV-curable composition of the present invention is also suitable for use as a potting agent, particularly an insulating potting agent for electronic devices and electrical devices.
- composition of the present invention can be used as a material for forming a coating layer on a substrate surface, especially using an inkjet printing method, in which case the composition of the present invention contains component (E) as described above. is particularly preferred.
- Viscosity of curable composition The viscosity (mPa ⁇ s) of the composition at 25° C. was measured using a rotational viscometer (E-type viscometer VISCONIC EMD manufactured by Tokimec Co., Ltd.).
- [Dielectric constant of cured organopolysiloxane] A tin foil having a diameter of 33 mm and a thickness of 0.007 mm was press-bonded to both surfaces of the prepared organopolysiloxane cured product. In order to improve the adhesiveness between the cured product and the foil, they were pressure-bonded via a very small amount of silicone oil, if necessary. The capacitance was measured at room temperature and 100 KHz with an E4990A precision impedance analyzer manufactured by Keysight Technologies, to which parallel plate electrodes with a diameter of 30 mm were connected. The dielectric constant was calculated using the measured capacitance value, the separately measured thickness of the cured product, and the electrode area value.
- An ultraviolet curable composition having the composition (parts by mass) shown in Table 1 was prepared using the following components.
- S1a 1,3-bis[2-(3,4-epoxycyclohexyl)ethyl]-1,1,3,3-tetramethyldisiloxane
- S1b 1,1,1,3,5,5,5 -heptamethyl-3-[2-(3,4-epoxycyclohexyl)ethyl]trisiloxane
- A isobornyl acrylate
- B polyhexenylsilsesquioxane (average functionality 7.7)
- C1 Tinuvin (registered trademark) 384-2 maximum absorption wavelength: 350 nm; manufactured by BASF
- C2 Tinuvin (registered trademark) 477 maximum absorption wavelength: 360 nm; manufactured by BASF)
- FDB-009 maximum absorption wavelength: 402 nm; manufactured by Yamada Chemical Industry
- the ultraviolet curable compositions of the present invention have viscosities at 25°C that are suitable for application to substrates as coating agents, particularly for application by inkjet printing. and the curable composition and the cured product obtained therefrom have high transparency.
- the present curable composition has good wettability with respect to substrates, and the addition of component (E) can further improve the wettability of the composition with respect to substrates.
- the cured product obtained from the curable composition of the present invention has a large UV shielding effect in a predetermined wavelength range (360 to 405 nm), and the curable composition of the present invention is excellent in UV curability.
- compositions (Comparative Examples 1 and 2) that do not contain the component (C) show no UV shielding effect.
- compositions containing a large amount of component (C) (Comparative Examples 3 and 4) are inferior in UV curability.
- the curable composition of the present invention is characterized in that it provides a cured product having a high UV shielding effect and can be rapidly cured with UV rays.
- the ultraviolet curable composition of the present invention is used for the above applications, particularly by shielding ultraviolet rays in the wavelength range of 360 to 405 nm, so that the quality stability should be improved, such as a touch panel and a display device, especially flexible display insulation. It is suitable as a material for forming layers.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
(S1)紫外線硬化性官能基を有するオルガノポリシロキサン及び/又はオルガノシラン、
(S2)(A)紫外線硬化性官能基を有し、且つケイ素原子を有するか又はケイ素原子を有しない化合物及び(B)紫外線硬化性官能基を有しないオルガノポリシロキサンからなる混合物
から選択される一種以上の有機ケイ素化合物を含む成分(S)、及び紫外線吸収能を有する化合物(C)を併用することによって得られる紫外線硬化性組成物が、良好な紫外線吸収機能を有し、低い粘度を有し、基材へ塗布する場合の作業性に優れ、かつその硬化物が優れた力学物性調整能を示すことを発見して完成したものである。
(S1)紫外線硬化性官能基を有するオルガノポリシロキサン及び/又はオルガノシラン、
(S2)(A)紫外線硬化性官能基を有し、且つケイ素原子を有するか又はケイ素原子を有しない化合物、及び(B)紫外線硬化性官能基を有しないオルガノポリシロキサンを5:95~95:5(A:B)の質量比で含む混合物、
並びに
(C)紫外線吸収性化合物 0.01~10質量部(但し、成分(S)及び成分(C)の合計を100質量部とする)、を併用することによって得られる紫外線硬化性組成物に関し、この紫外線硬化性組成物は、良好な紫外線吸収機能を有し、低い粘度を有し、基材へ塗布する場合の作業性に優れ、かつその硬化物が優れた力学物性調整能を示す。
ここで、波長域360~405nmの少なくとも1点において、上記硬化物の光透過率が50%以下となるという意味は、300~800nmの範囲にわたって硬化物の光透過率を測定したときに、波長域360~405nmの範囲の少なくとも1点で光透過率が50%以下となるという意味である。
また、紫外線硬化性組成物が硬化するという意味は、光照射を行った後、組成物の表面を指で触れたときに、組成物が指についてこないことをいう。
RcR’dSiO(4-c―d)/2 (2)
(式中、Rは、紫外線硬化性官能基であり、
R’は、紫外線反応性紫外線硬化性官能基を除く一価炭化水素基、水酸基、及びアルコキシ基から選ばれる基であり、
c及びdは次の条件:1<c+d≦4及び0.05≦c/(c+d)≦0.25を満たす数であり、分子中のRの数は1である。)
で表される直鎖状、分岐状、又は環状のオルガノシラン及びオルガノポリシロキサンからなる群から選択される有機ケイ素化合物であることが好ましい。
RaR’bSiO(4-a―b)/2 (1)
(式(1)中、Rは、紫外線硬化性官能基であり、
R’は、紫外線硬化性官能基を除く一価炭化水素基、水酸基、及びアルコキシ基から選ばれる基であり、
a及びbは次の条件:1≦a+b≦3及び0.01≦a/(a+b)≦0.34を満たす数であり、分子中に少なくとも2個のRを有する。)
で表される直鎖状、分岐状、又は環状のオルガノポリシロキサンであることが好ましい。
または、下記式(5’):
または、下記式(6):
RSiR’3 (6)
(式(6)中、Rは、紫外線硬化性官能基であり、R’は、前記紫外線硬化性官能基を除く一価炭化水素基、水酸基、及びアルコキシ基から選ばれる基である)で表されるオルガノシランからなる群から選択される、紫外線硬化性官能基を分子中に1個有するオルガノポリシロキサン及び/又はオルガノシランであることが好ましい。
平均単位式:
(R3SiO1/2)e(R2SiO2/2)f(RSiO3/2)g(SiO4/2)h (4)
(式(4)中、Rは、それぞれ独立に、紫外線硬化性官能基及び非置換又はフッ素で置換された一価炭化水素基から選ばれる基であり、全てのRのうち、少なくとも2個は紫外線硬化性官能基であり、(g+h)は正数であり、eは0又は正数であり、fは0~20の範囲内の数である。)
で表されるオルガノポリシロキサン、
下記式(5):
及びそれらから任意に選択される2種以上のオルガノポリシロキサンの混合物からなる群から選択される、紫外線硬化性官能基を有する1種類以上のオルガノポリシロキサンであることが好ましい。
(S1-1)一分子中に平均して2個以上のエポキシ基含有基を有する1種以上のオルガノポリシロキサン、及び
(S1-2)一分子中に1個のエポキシ基含有基を有する1種以上のオルガノポリシロキサン及び/又はオルガノシランからなる群から選択される1種以上の有機ケイ素化合物を成分(S1-1)及び成分(S1-2)が100/0~0/100(S1-1/S1-2)となる質量比で含む混合物であることが好ましい。
(S1-1-1):
1,3-ビス[2-(3,4-エポキシシクロヘキシル)エチル]-1,1,3,3-テトラメチルジシロキサン、1,5-ビス[2-(3,4-エポキシシクロヘキシル)エチル]-1,1,3,3,5,5-ヘキサメチルトリシロキサン、1,1,3,3,5,5,7,7,9,9-デカメチル-1,9-ビス[2-(3,4-エポキシシクロヘキシル)エチル]ペンタシロキサン、メチル(トリス[2-(3,4-エポキシシクロヘキシル)エチル]ジメチルシロキシ)シラン、テトラキス([2-(3,4-エポキシシクロヘキシル)エチル]ジメチルシロキシ)シラン、1,3,5,7-テトラメチル-1,3,5,7-テトラ[2-(3,4-エポキシシクロヘキシル)エチル]-シクロテトラシロキサン、1,3-ビス(3-グリシドキシプロピル)-1,1,3,3-テトラメチルジシロキサン、1,5-ビス(3-グリシドキシプロピル)-1,1,3,3,5,5-ヘキサメチルトリシロキサン、1,1,3,3,5,5,7,7,9,9-デカメチル-1,9-ビス(3-グリシドキシプロピル)ペンタシロキサンメチル[トリス(3-グリシドキシプロピル)ジメチルシロキシ]シラン、テトラキス[(3-グリシドキシプロピル)ジメチルシロキシ]シラン、1,3,5,7-テトラメチル-1,3,5,7-テトラ(3-グリシドキシプロピル)-シクロテトラシロキサン。
(B1)一分子中に3個以上のアルケニル基を有し、紫外線硬化性官能基を有しないオルガノポリシロキサン、
(B2)一分子中に2個以上のアルケニル基を有し、ビニル基の含有率が5質量%以上であり、かつ紫外線硬化性官能基を有しないオルガノポリシロキサン。
RaR’bSiO(4-a―b)/2 (7)
(式(7)中、Rは、アルケニル基であり、
R’は、アルケニル基を除く一価炭化水素基、水酸基、及びアルコキシ基から選ばれる基であり、
a及びbは次の条件:1≦a+b<3及び0.1≦a/(a+b)≦1.0を満たす数であり、分子中に少なくとも2個のRを有する。)
で表される直鎖状、分岐状、又は環状のオルガノポリシロキサンである。
平均単位式:
(R3SiO1/2)e(R2SiO2/2)f(RSiO3/2)g(SiO4/2)h (9)
(式(9)中、Rは、それぞれ独立に、アルケニル基及び非置換又はフッ素で置換された一価炭化水素基から選ばれる基であり、全てのRのうち、少なくとも2個はアルケニル基であり、(g+h)は正数であり、eは0又は正数であり、fは0~100の範囲内の数である)で表されるオルガノポリシロキサン、
下記式(10):
及びこれらのオルガノポリシロキサンの混合物からなる群から選択される、分子内にアルケニル基を2個以上有する1種類以上のオルガノポリシロキサンである。
本発明の紫外線硬化性組成物から得られる厚さ10μmの硬化物は、波長域360~405nmにおける光透過率の最も低い値が25%以下であることが好ましい。
本発明の紫外線硬化性組成物は、下記(S1)又は成分(S2):
(S1)紫外線硬化性官能基を有するオルガノポリシロキサン及び/又はオルガノシラン、
(S2)(A)紫外線硬化性官能基を有し、且つケイ素原子を有するか又はケイ素原子を有しない化合物及び(B)紫外線硬化性官能基を有しないオルガノポリシロキサンを5:95~95:5(A:B)の質量比で含む混合物、
から選択される一種以上の成分(S) 90~99.99質量部(成分(S)の総量)、及び、
(C)紫外線吸収性化合物 0.01~10質量部(但し、成分(S)及び成分(C)の合計は100質量部である)
を含有してなる紫外線硬化性組成物であって、
硬化後の厚さが10μmとなるように組成物を任意の基材に塗布し、波長365~405nmから選ばれる少なくとも一つの波長における積算光量が2~8J/cm2となるように光照射を行った場合に、照射完了時点またはそれから5分以内に組成物が硬化可能であり、得られた厚さ10μmの硬化物の、波長450nmにおける光透過率が98%以上であり、かつ、波長域360~405nmの少なくとも1点において、光透過率が50%以下となることを特徴とするものである。
成分(S)は硬化性組成物の主成分であり、成分(S1)から選択される1種類以上の化合物、又は成分(S2)から選択される1種類以上の化合物を用いることができる。
成分(S1)は上述したとおり、一分子中に平均して2個以上の紫外線硬化性官能基を有する1種以上のオルガノポリシロキサン(S1-A)、一分子中に1個の紫外線硬化性官能基を有する1種以上のオルガノポリシロキサン及び/又はオルガノシラン(S1-B)、あるいはこれらの任意の混合物であることができる。
成分(S1-A)のポリシロキサンは下記平均組成式:
RaR’bSiO(4-a―b)/2 (1)
で表される直鎖状、分岐状、又は環状の、好ましくは直鎖状又は分岐状の、特に好ましくは直鎖状のオルガノポリシロキサンである。
Rは紫外線硬化性官能基であり、
R’は紫外線硬化性官能基を除く、一価炭化水素基、水酸基、及びアルコキシ基から選ばれる基であり、
a及びbは次の条件:1≦a+b≦3及び0.01≦a/(a+b)≦0.34、好ましくは2≦a+b≦3及び0.05≦a/(a+b)≦0.34を満たす数であり、平均して一分子中に少なくとも2個のRを有する。
紫外線硬化性官能基としては、1種以上のエポキシ基含有基であることが好ましい。特に好ましい基として、グリシジルオキシアルキル基、特に3-グリシジルオキシプロピル基、エポキシシクロヘキシルアルキル基、特に3,4-エポキシシクロヘキシルエチル基を挙げることができる。
平均単位式:
(R3SiO1/2)e(R2SiO2/2)f(RSiO3/2)g(SiO4/2)h (4)
式(4)中、Rは、それぞれ独立に、紫外線硬化性官能基及び非置換又はフッ素で置換された一価炭化水素基から選ばれる基であり、全てのRのうち、少なくとも2個は紫外線硬化性官能基であり、(g+h)は正数であり、eは0又は正数であり、fは0~20の範囲内の数である。
紫外線硬化性官能基及び一価炭化水素基は、上で式(1)について定義したとおりである。また、式(4)で表されるオルガノポリシロキサンの好ましい粘度も上において式(1)で表されるオルガノポリシロキサンについて規定したとおりである。
成分(S1)としては、特に、上記式(3)で表されるオルガノポリシロキサン、式(5)で表される環状オルガノポリシロキサン、及びそれらの組み合わせからなる群から選択される1種以上の有機ケイ素化合物を用いることが好ましい。
成分(S1-B)は、オルガノシラン又はオルガノポリシロキサン骨格に、一分子中に1個の紫外線硬化性官能基を有する有機ケイ素化合物であり、主に、本発明の組成物から得られる硬化物の架橋密度を制御し、硬化物の物性を調節し、同時に、当該組成物の粘度を低減させる効果を有する。この目的を達成できる限りその分子構造は任意のものであることができる。一例として、成分(S1-B)の有機ケイ素化合物は、
下記平均組成式;
RcR’dSiO(4-c―d)/2 (2)
(式(2)中、Rは、紫外線硬化性官能基であり、
R’は、紫外線硬化性官能基を除く、一価炭化水素基、水酸基、及びアルコキシ基から選ばれる基であり、
c及びdは次の条件:1≦c+d≦4及び0.05≦c/(c+d)≦0.25を満たす数であり、分子中のRの数は1である。)
で表されるオルガノシラン、あるいは直鎖状、分岐状、又は環状のオルガノポリシロキサンである。これらのオルガノシラン及びオルガノポリシロキサンからなる群から選択される1種を用いることも、任意の2種以上を組み合わせて用いることもできる。本明細書では、以下において簡単のために、オルガノシラン及び/又はオルガノポリシロキサンをまとめて有機ケイ素化合物ともいう。
紫外線硬化性官能基は、1種以上のエポキシ基含有基であることが好ましい。特に好ましい基として、グリシジルオキシアルキル基、例えば、グリシジルオキシプロピル基、エポキシシクロヘキシルアルキル基、特に3,4-エポキシシクロヘキシルエチル基を挙げることができる。
式:
式: RSiR’3 (6)
式(6)中、Rは、紫外線硬化性官能基であり、R’は、紫外線硬化性官能基を除く一価炭化水素基、水酸基、及びアルコキシ基から選ばれる基である。
紫外線硬化性官能基及び一価炭化水素基は、先に式(2)について定義したとおりであり、アルコキシ基は、炭素数1~20、好ましくは炭素数1~6、さらに好ましくは炭素数1~3のアルコキシ基、あるいは炭素数5~20のシクロアルキル基である。具体的には、メトキシ基、エトキシ基、イソプロポキシ基、シクロペンチル基、又はシクロヘキシル基が好ましい。
1,3-ビス[2-(3,4-エポキシシクロヘキシル)エチル]-1,1,3,3-テトラメチルジシロキサン、1,5-ビス[2-(3,4-エポキシシクロヘキシル)エチル]-1,1,3,3,5,5-ヘキサメチルトリシロキサン、1,1,3,3,5,5,7,7,9,9-デカメチル-1,9-ビス[2-(3,4-エポキシシクロヘキシル)エチル]ペンタシロキサン、メチル(トリス[2-(3,4-エポキシシクロヘキシル)エチル]ジメチルシロキシ)シラン、テトラキス([2-(3,4-エポキシシクロヘキシル)エチル]ジメチルシロキシ)シラン、1,3,5,7-テトラメチル-1,3,5,7-テトラ[2-(3,4-エポキシシクロヘキシル)エチル]-シクロテトラシロキサン、1,3-ビス(3-グリシドキシプロピル)-1,1,3,3-テトラメチルジシロキサン、1,5-ビス(3-グリシドキシプロピル)-1,1,3,3,5,5-ヘキサメチルトリシロキサン、1,1,3,3,5,5,7,7,9,9-デカメチル-1,9-ビス(3-グリシドキシプロピル)ペンタシロキサン、メチル[トリス(3-グリシドキシプロピル)ジメチルシロキシ]シラン、テトラキス[(3-グリシドキシプロピル)ジメチルシロキシ]シラン、及び1,3,5,7-テトラメチル-1,3,5,7-テトラ(3-グリシドキシプロピル)-シクロテトラシロキサン
からなる群から選択される1種の化合物又は2種以上の化合物の組み合わせと、成分(S1-B)として1,1,1,3,5,5,5-ヘプタメチル-3-[2-(3,4-エポキシシクロヘキシル)エチル]トリシロキサンを併用することが好ましく、成分(S1-B)と成分(S1-A)の質量比は、好ましくは100/0~20/80(S1-B/S1-A)、さらに好ましくは100/0~25/75、特に好ましくは100/0~30/70の範囲である。しかし、この成分(S1-A)と成分(S1-B)の質量比は特に好ましい範囲を規定した値であって、上記の成分(S1-A)のみを用いて、本発明の硬化性組成物を調製することもできる。したがって、成分(S1-B)と成分(S1-A)の質量比は100/0~0/100であってよい。
本発明の硬化性組成物には、上記成分(S1)、すなわち成分(S1-A)及び/又は成分(S1-B)に加えて、一分子中に1個以上の紫外線硬化性官能基を有し且つケイ素原子を有しない化合物(成分(D))をさらに添加してもよい。特に成分(S1)として成分(S1-B)のみを用いる場合には、成分(S1-B)に加えて成分(D)を用いることが好ましい。成分(S1-B)に成分(D)を併用することによって、組成物の硬化性が改善される場合がある。
本発明の紫外線硬化性組成物に用いる光カチオン重合開始剤は、当技術分野で公知のものから任意に選択して用いることができ、特に特定のものに限定されない。光カチオン重合開始剤には、ジアゾニウム塩、スルホニウム塩、ヨードニウム塩、ホスホニウム塩などの強酸発生化合物が知られており、これらを用いることができる。光カチオン重合開始剤の例として、ビス(4-tert-ブチルフェニル)ヨードニウム ヘキサフルオロホスフェート、シクロプロピルジフェニルスルホニウム テトラフルオロボレート、ジメチルフェナシルスルホニウム テトラフルオロボレート、ジフェニルヨードニウム ヘキサフルオロホスフェート、ジフェニルヨードニウム ヘキサフルオロアルセナート、ジフェニルヨードニウム テトラフルオロメタンスルホネート、2-(3,4-ジメトキシスチリル)-4,6-ビス(トリクロロメチル)-1,3,5-トリアジン、2-[2-(フラン-2-イル)ビニル]-4,6-ビス(トリクロロメチル)-1,3,5-トリアジン、4-イソプロピル-4’-メチルジフェニルヨードニウム テトラキス(ペンタフルオロフェニル)ボレート、2-[2-(5-メチルフラン-2-イル)ビニル]-4,6-ビス(トリクロロメチル)-1,3,5-トリアジン、2-(4-メトキシフェニル)-4,6-ビス(トリクロロメチル)-1,3,5-トリアジン、2-(4-メトキシスチリル)-4,6-ビス(トリクロロメチル)-1,3,5-トリアジン、4-ニトロベンゼンジアゾニウム テトラフルオロボレート、トリフェニルスルホニウム テトラフルオロボレート、トリフェニルスルホニウムブロマイド、トリ-p-トリルスルホニウム ヘキサフルオロホスフェート、トリ-p-トリルスルホニウム トリフルオロメタンスルホネート、ジフェニルヨードニウム トリフラート、トリフェニルスルホニウム トリフラート、ジフェニルヨードニウム ナイトレート、ビス(4-tert-ブチルフェニル)ヨードニウム パーフルオロ-1-ブタンスルホネート、ビス(4-tert-ブチルフェニル)ヨードニウム トリフラート、トリフェニルスルホニウムパーフルオロ-1-ブタンスルホナート、N-ヒドロキシナフタルイミド トリフラート、p-トルエンスルホネート、ジフェニルヨードニウム p-トルエンスルホネート、(4-tert-ブチルフェニル)ジフェニルスルホニウム トリフラート、トリス(4-tert-ブチルフェニル)スルホニウム トリフラート、N-ヒドロキシ-5-ノルボルネン-2,3-ジカルボキシミド ペルフルオロ-1-ブタンスルホナート、(4-フェニルチオフェニル)ジフェニルスルホニウム トリフラート、及び4-(フェニルチオ)フェニルジフェニルスルホニウム トリエチルトリフルオロホスフェートなどが挙げられるがこれらに限定されない。光カチオン重合開始剤として、上記化合物のほかにも、Omnicat 250、Omnicat 270(以上、IGM Resins B.V.社)、CPI-310B, IK-1(以上、サンアプロ株式会社)、DTS-200 (みどり化学株式会社)、及びIrgacure 290(BASF社)などの市販されている光開始剤を挙げることができる。
成分(S2)は、(A)紫外線硬化性官能基を有し、且つケイ素原子を有するか又はケイ素原子を有しない化合物及び(B)紫外線硬化性官能基を有しないオルガノポリシロキサンを5:95~95:5(A:B)の質量比で含む混合物である。
成分(A)は、したがって、(A1)紫外線硬化性官能基を有し且つケイ素原子を有する化合物、(A2)紫外線硬化性官能基を有し且つケイ素原子を有しない化合物、又は(A1)と(A2)の組み合わせであり、各場合に、(A1)及び(A2)の化合物はそれぞれ1種又は2種以上の化合物の組み合わせであることができる。
成分(A1)は分子内に紫外線硬化性官能基及びケイ素原子を有する化合物である。成分(A1)の化合物は、上述した成分(S1)、(S1-A)、(S1-B)、(S-1)、及び(S1-2)からなる群から選択される化合物又は2種以上の化合物の混合物であることができる。紫外線硬化性官能基の種類を除き、成分(S1)について好ましい態様、例えば好ましい粘度、一分子当たりの好ましい紫外線硬化性官能基数などは、成分(A1)についても好ましい。
成分(A2)は分子内に紫外線硬化性官能基を有し且つケイ素原子を有しない化合物である。成分(A2)の紫外線硬化性官能基は、成分(S1)の紫外線硬化性官能基と同様、光開始剤の存在下又は不存在下で、紫外線の照射によって互いの間に結合を生じることができる有機基である。紫外線硬化性官能基の例としては、ラジカル重合性基及びカチオン重合性基を挙げることができるが、ラジカル重合性基、特にアクリロキシ基が好ましい。ラジカル重合性基は、成分(S1)に関連して説明したものが挙げられる。具体的には、一分子中に1個以上のアクリロキシ基を有する化合物が好ましい。本発明の目的を達成できる限りその分子構造に制限はなく、直鎖状、分岐状、環状、かご状等、任意のものであることができる。
成分(B)は、紫外線硬化性官能基を有しないオルガノポリシロキサンである。成分(B)は、特に、下記(B1)及び(B2)から選択される一種以上のアルケニル基含有オルガノポリシロキサンであることが好ましい。
(B1)一分子中に3個以上のアルケニル基を有し、紫外線硬化性官能基を有しないオルガノポリシロキサン、
(B2)一分子中に2個以上のアルケニル基を有し、ビニル基の含有率が5質量%以上であり、かつ紫外線硬化性官能基を有しないオルガノポリシロキサン。アルケニル基は末端アルケニル基であることが好ましい。なお、ビニル基の含有率とは化合物に含まれる全てのアルケニル基のビニル基部分(CH2=CH-)の質量が分子全体の質量に占める割合をいう。
RaR’bSiO(4-a―b)/2 (7)
(式(7)中、Rは、アルケニル基であり、
R’は、アルケニル基を除く一価炭化水素基、水酸基、及びアルコキシ基から選ばれる基であり、
a及びbは次の条件:1≦a+b<3及び0.1≦a/(a+b)≦1.0を満たす数であり、分子中に少なくとも2個のアルケニル基(R)を有する。)
で表される直鎖状、分岐状、又は環状のアルケニル基含有オルガノポリシロキサンであることができる。
平均単位式:
(R3SiO1/2)e(R2SiO2/2)f(RSiO3/2)g(SiO4/2)h (9)
式(9)中、Rは、それぞれ独立に、アルケニル基及び非置換又はフッ素で置換された一価炭化水素基から選ばれる基であり、全てのRのうち、少なくとも2個はアルケニル基であり、(g+h)は正数であり、eは0又は正数であり、fは0~100の範囲内の数である。
成分(B)としては、特に、上記式(8)で表されるオルガノポリシロキサン、式(9)で表される分岐状オルガノポリシロキサン、及びそれらの組み合わせからなる群から選択される1種以上のオルガノポリシロキサンを用いることが好ましい。
上述したとおり、本発明の成分(S2)は上述した成分(A)及び成分(B)を5:95~95:5(A:B)の質量比で含む混合物である。すなわち、成分(A)と成分(B)の混合比率は、成分(A)と成分(B)の総量100質量%に対し、成分(A)の割合は5~95質量%、成分(B)の割合は95~5質量%である。成分(A)と(B)の割合がこの範囲にある場合、硬化性組成物の粘度を適正にし、良好な紫外線硬化性を保持し、かつ得られる硬化物の力学特性、特に引張伸度の大きな材料を設計することができる。成分(A)の比率を高くすることにより、硬化物の硬度を高く設計し易い。成分(A)の好ましい割合は、成分(A)及び(B)の合計量の15質量%以上、85質量%以下、より好ましくは20質量%以上、80質量%以下、さらに好ましくは25質量%以上、75質量%以下である。
本発明の紫外線硬化性組成物の成分(S)として上記成分(A)及び(B)を用いる場合は、成分(A)及び成分(B)に加えて、所望により光重合開始剤を添加することができる。成分(A)が有する紫外線硬化性官能基がカチオン重合性官能基である場合には、本発明の成分(S)として成分(S1)を用いる態様と関連して説明した紫外線硬化性官能基がカチオン重合性官能基である場合に用いることができる光カチオン重合開始剤を用いることが好ましい。ここでも、上述した光カチオン重合性開始剤についての記載をそのまま適用することができる。また、成分(A)が有する紫外線硬化性官能基がラジカル重合性基である場合、光重合開始剤として光ラジカル重合開始剤を用いることが好ましい。成分(A)とともに光ラジカル重合開始剤を用いることによって、紫外線又は電子線の照射によってフリーラジカルが発生し、それがラジカル重合反応を引き起こして本発明の組成物を硬化させることができる。電子線照射によって本発明の組成物を硬化させる場合には、重合開始剤は通常不要である。
本発明の硬化性組成物の成分(S)は、上述した成分(S1)から選択される1種類以上の成分、又は成分(S2)から選択される1種類以上の成分からなる。すなわち、成分(S)は成分(S1)のみ、又は成分(S2)のみからなる。
(1)成分(S)が成分(S1)からなり、成分(S1)の紫外線硬化性官能基の数が、一分子当たり平均して2個である。
(2)成分(S)が成分(S1)からなり、成分(S1)が、紫外線硬化性官能基を分子中に1個有するオルガノポリシロキサンである。
(3)(i)成分(S)が成分(S1)からなり、成分(S1)が有する紫外線硬化性官能基が、アクリロキシ基含有基、メタクリロキシ基含有基、エポキシ基含有基、オキセタン基含有基、及びビニルエーテル基含有基からなる群から選択される官能基である。
(ii)成分(S)が成分(S2)からなり、成分(S2)中の成分(A)が有する紫外線硬化性官能基が、アクリロキシ基含有基、メタクリロキシ基含有基、エポキシ基含有基、オキセタン基含有基、及びビニルエーテル基含有基からなる群から選択される官能基である。
(4)成分(S)が成分(S1)からなり、成分(S1)の紫外線硬化性官能基がエポキシ基含有基である。好ましくは、成分(S1)がエポキシ官能性オルガノポリシロキサンのみからなる、又はエポキシ官能性オルガノポリシロキサンを含む。
(5)成分(S)が成分(S2)からなり、成分(S2)の成分(A)が紫外線硬化性官能基としてアクリロキシ基を有し且つケイ素原子を有する化合物及び/又は紫外線硬化性官能基としてアクリロキシ基を有し且つケイ素原子を有しない化合物である。
(6)成分(S)が成分(S2)からなり、成分(S2)の成分(A)が紫外線硬化性官能基としてアクリロキシ基を有し且つケイ素原子を有する化合物及び/又は紫外線硬化性官能基としてアクリロキシ基を有し且つケイ素原子を有しない化合物であり、成分(B)がアルケニル基を有するオルガノポリシロキサンである。この場合、成分(A)は、ケイ素原子を有しない化合物であることがさらに好ましい。
(7)成分(S)が成分(S2)からなり、成分(S2)の成分(A)が紫外線硬化性基としてアクリロキシ基を1個有する一種の化合物又二種以上の化合物の混合物である。
(8)成分(S)が成分(S2)からなり、成分(S2)の成分(A)が紫外線硬化性基としてアクリロキシ基を1個有する一種以上の化合物とアクリロキシ基を2個以上有する一種以上の化合物との混合物である。
(9)成分(S)が成分(S2)からなり、成分(S2)の成分(A)が紫外線硬化性基としてアクリロキシ基を1個以上有し且つケイ素原子を有しない化合物である。
(10)成分(S)が成分(S2)からなり、成分(S2)の成分(B)が(RSiO3/2)単位を有するオルガノポリシロキサンであるか、(RSiO3/2)単位を有するオルガノポリシロキサンを含む。この場合に好ましくは、成分(B)はアルケニル基含有シルセスキオキサンである。
(11)成分(S)が成分(S2)からなり、成分(S2)の成分(B)が、一分子中に3個以上のアルケニル基を有するオルガノポリシロキサンであるか、一分子中に3個以上のアルケニル基を有するオルガノポリシロキサンを含む。この場合に好ましくは、成分(B)はアルケニル基含有シルセスキオキサンである。
(12)成分(S)が成分(S2)からなり、成分(S2)の成分(B)がアルケニル基を有するオルガノポリシロキサンであり、そのアルケニル基が炭素数3~8のアルケニル基である。
本発明の成分(C)の紫外線吸収性化合物は、紫外線硬化性組成物から得られる硬化物中において、紫外線を吸収し、有効な紫外線遮蔽効果をもたらす成分である。紫外線吸収性化合物は当技術分野においてよく知られている化合物であり、多くの種類の紫外線吸収性化合物がいわゆる紫外線吸収剤として市販されている。本発明の紫外線硬化性組成物中の成分(S)に対して良好な混和性を有する紫外線吸収性化合物を用いることが好ましい。成分(C)は、本発明の紫外線硬化性組成物を硬化させて得られる、厚さ10μmの硬化物が、可視光波長450nmにおいて98%以上の光透過率を示すようにその種類及び添加量を調節することができる。その一方、紫外線波長域360~405nmにおいては、良好な紫外線遮蔽効果を示し、この波長域における上記硬化物の光透過率の最も低い値は50%以下であるようにすることができる。これらの条件を満足させる限りにおいては、成分(C)の紫外線吸収性化合物の化学構造に制限はないが、340~420nmの波長域に極大吸収波長を有する化合物であることが好ましい。
本発明の紫外線硬化性組成物をコーティング剤として基材表面に任意の方法を用いて適用したときに、基材への組成物の濡れ性を向上させて、欠陥のない塗膜を形成させるためには、上述した成分を含む本発明の組成物にさらに以下のものから選択される成分(E)を添加することができる。本発明の組成物を基材にコーティングするための方法として、インクジェット印刷法を使用することが特に好ましい。したがって、成分(E)は、本発明の紫外線硬化性オルガノポリシロキサン組成物の基材への濡れ性を向上させ、特にインクジェット印刷特性を著しく改良せしめる成分である。成分(E)は、以下の(E1)、(E2)、及び(E3)からなる群より選択される少なくとも1種の化合物である。
成分(E1)は、ケイ素原子を含まず、アクリル系でない非イオン性界面活性剤、すなわち非アクリル系非イオン性界面活性剤である。非アクリル系とは、界面活性剤がその分子内に(メタ)アクリレート基を有していないものをいう。成分(E1)として用いることができる界面活性剤として、グリセリン脂肪酸エステル、ソルビタン脂肪酸エステル、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルフェニルエーテル、アルキルグリコシド、アセチレングリコールポリエーテル等の有機系非イオン性界面活性剤、及びフッ素系非イオン性界面活性剤等を挙げることができ、これらの1種又は2種以上を組み合わせて用いることができる。成分(E1)の具体例としては、有機系非イオン性界面活性剤として花王株式会社製エマルゲンシリーズ、同レオドールシリーズ、エボニックインダストリーズ製サーフィノール400シリーズ、日信化学工業株式会社製オルフィンEシリーズが挙げられ、フッ素系非イオン性界面活性剤として3M製FC-4400シリーズ、DIC株式会社製メガファック550及び560シリーズが挙げられる。
これらの中でも、特にアルキノールポリエーテルである、サーフィノール400シリーズ、オルフィンEシリーズが好ましい。
上記成分に加えて、所望によりさらなる添加剤を本発明の組成物に添加してもよい。添加剤としては、以下に挙げるものを例示できるが、これらに限定されない。
本発明の組成物には、組成物に接触している基材に対する接着性や密着性を向上させるために接着促進剤を添加することができる。本発明の硬化性組成物をコーティング剤、シーリング材などの、基材に対する接着性又は密着性が必要な用途に用いる場合には、本発明の硬化性組成物に接着性付与剤を添加することが好ましい。この接着促進剤としては、本発明の組成物の硬化反応を阻害しない限り、任意の公知の接着促進剤を用いることができる。
本発明の組成物には、上述した接着性付与剤に加えて、あるいは接着性付与剤に代えて、所望によりその他の添加剤を添加してもよい。用いることができる添加剤としては、レベリング剤、上述した接着性付与剤として挙げたものに含まれないシランカップリング剤、紫外線吸収剤、酸化防止剤、重合禁止剤、フィラー(補強性フィラー、絶縁性フィラー、及び熱伝導性フィラー等の機能性フィラー)などが挙げられる。必要に応じて、適切な添加剤を本発明の組成物に添加することができる。また、本発明の組成物には必要に応じて、特にポッティング剤又はシール材として用いる場合には、チキソ性付与剤を添加してもよい。
本発明の紫外線硬化性組成物は、紫外線による硬化だけでなく、電子線を用いて硬化させることもでき、それも本発明の一つの態様である。
回転粘度計(トキメック株式会社製、E型粘度計VISCONIC EMD)を使用して、25℃における組成物の粘度(mPa・s)を測定した。
目視によって、硬化性組成物及びそれから得られた硬化物の外観を観察して評価した。
下記表1に記載した量(質量部)の各材料を褐色プラスチック製容器に入れ、プラネタリーミキサーを使用して良く混合し、硬化性組成物を調製した。
厚さ0.7mmの二枚の光学ガラスの間に、約0.02gの硬化性組成物を挟み、外側から片方のガラスを通して、波長405nmのLED光を4J/cm2のエネルギー量(すなわち積算光量)で照射することにより、組成物を硬化させて、直径40~45mm、厚さ10±1μm(マイクロメートル)の硬化物を作製した。この試料の透過率(単位:%)を日本分光(株)製、V-650紫外・可視分光光度計により25℃にて測定した。透過率の測定範囲は300nm~800nmである。
硬化性組成物2マイクロリットルを窒化ケイ素コートガラス基板に滴下し、滴下直後及び15秒経過後の硬化性組成物の接触角(単位:°)を、協和界面化学株式会社製の接触角測定装置DM-700により23℃にて測定した。
フッ素ポリマー系剥離剤がコーティングされたPETフィルム上に、内径40mmの円形の空孔を有する厚さ1mmの金型を載せ、その空孔中に約1.3gの硬化性組成物を流し込んだ。当該組成物の上に、前記と同様のPETフィルムをかぶせ、さらにその上に厚さ10mmのガラス板を載せた。この上から、波長405nmのLED光を4J/cm2のエネルギー量で照射することにより、組成物を硬化させて、直径40mm、厚さ1mmの円板状オルガノポリシロキサン硬化物を作製した。
作製したオルガノポリシロキサン硬化物の両面に直径33mm、厚さ0.007mmの錫箔を圧着した。該硬化物と箔の密着性を改善するため、必要に応じ、微量のシリコーンオイルを介して圧着した。直径30mmの平行板電極を接続したキーサイトテクノロジー製E4990Aプレシジョンインピーダンス・アナライザにて室温、100KHzにおける静電容量を測定した。測定した静電容量の値と、別途測定した硬化物の厚さ、及び電極面積の値を用いて、比誘電率を算出した。
下記の各成分を用いて、表1に示す組成(質量部)の紫外線硬化性組成物を調製した。
(S1a)1,3-ビス[2-(3,4-エポキシシクロヘキシル)エチル]-1,1,3,3-テトラメチルジシロキサン
(S1b)1,1,1,3,5,5,5-ヘプタメチル-3-[2-(3,4-エポキシシクロヘキシル)エチル]トリシロキサン
(A)イソボルニルアクリレート
(B)ポリヘキセニルシルセスキオキサン(平均官能基数7.7)
(C1)Tinuvin(登録商標)384-2(極大吸収波長:350nm;BASF製)
(C2)Tinuvin(登録商標)477(極大吸収波長:360nm;BASF製)
(C3)FDB-009(極大吸収波長:402nm;山田化学工業製)
(E)DOWSIL(登録商標)SH 200 Fluid (20 cSt)(ダウ・ケミカル・カンパニー製)
(F1)4-イソプロピル-4’-メチルジフェニルヨードニウム-テトラキス(ペンタフルオロフェニル)ボレート
(F2)2-イソプロピルチオキサントン
(F3)Omnirad(登録商標)TPO-L(IGM Resins製)
(G)ジブチルヒドロキシトルエン
このように、本発明の硬化性組成物は、紫外線遮断効果が大きい硬化物をもたらすと同時に、迅速に紫外線硬化可能であるという特徴を有する。
Claims (38)
- (S)1種類以上の下記の成分(S1)又は成分(S2) 90~99.99質量部:
(S1)紫外線硬化性官能基を有するオルガノポリシロキサン及び/又はオルガノシラン、
(S2)(A)紫外線硬化性官能基を有し、且つケイ素原子を有するか又はケイ素原子を有しない化合物及び(B)紫外線硬化性官能基を有しないオルガノポリシロキサンを5:95~95:5の質量比で含む混合物、及び
(C)紫外線吸収性化合物 0.01~10質量部(但し、成分(S)及び成分(C)の合計を100質量部とする)
を含有してなり、硬化後の厚さが10μmとなるように組成物を任意の基材に塗布し、波長365~405nmから選ばれる少なくとも一つの波長における積算光量が2~8J/cm2となるように光照射を行った場合に、照射完了時点またはそれから5分以内に組成物を硬化することができ、得られた厚さ10μmの硬化物の、波長450nmにおける光透過率が98%以上であり、かつ、波長域360~405nmの少なくとも1点において、光透過率が50%以下となる、紫外線硬化性組成物。 - 有機溶媒を実質的に含まない、請求項1に記載の紫外線硬化性組成物。
- E型粘度計を用いて25℃で測定した組成物全体の粘度が、500mPa・s以下であることを特徴とする、請求項2に記載の紫外線硬化性組成物。
- 厚さ10μmの硬化物の、最も低い光透過率を示す波長域が385~400nmである、請求項2または3のいずれか1項に記載の紫外線硬化性組成物。
- 組成物中の成分(C)が、340~420nmの波長域に極大吸収波長を有する化合物である、請求項2~4のいずれか1項に記載の紫外線硬化性組成物。
- 成分(S1)及び成分(S2)(A)の紫外線硬化性官能基を有し、且つケイ素原子を有する化合物が、平均組成式:
RcR’dSiO(4-c―d)/2 (2)
(式中、Rは、紫外線硬化性官能基であり、
R’は、紫外線硬化性官能基を除く一価炭化水素基、水酸基、及びアルコキシ基から選ばれる基であり、
c及びdは次の条件:1<c+d≦4及び0.05≦c/(c+d)≦0.25を満たす数であり、分子中のRの数は1である。)
で表される直鎖状、分岐状、又は環状のオルガノシラン及びオルガノポリシロキサンからなる群から選択される有機ケイ素化合物である、請求項1~5のいずれか一項に記載の紫外線硬化性組成物。 - 成分(S1)及び成分(S2)(A)の紫外線硬化性官能基を有し且つケイ素原子を有する化合物が、平均組成式:
RaR’bSiO(4-a―b)/2 (1)
(式(1)中、Rは、紫外線硬化性官能基であり、
R’は、紫外線硬化性官能基を除く一価炭化水素基、水酸基、及びアルコキシ基から選ばれる基であり、
a及びbは次の条件:1≦a+b≦3及び0.01≦a/(a+b)≦0.34を満たす数であり、分子中に少なくとも2個のRを有する。)
で表される直鎖状、分岐状、又は環状のオルガノポリシロキサンである、請求項1~5のいずれか一項に記載の紫外線硬化性組成物。 - 成分(S1)のオルガノポリシロキサン及び/又はオルガノシラン及び成分(S2)中の成分(A)である紫外線硬化性官能基を有し且つケイ素原子を有する化合物が、下記式(3’):
または、下記式(5’):
または、下記式(6):
RSiR’3 (6)
(式(6)中、Rは、紫外線硬化性官能基であり、R’は、前記紫外線硬化性官能基を除く一価炭化水素基、水酸基、及びアルコキシ基から選ばれる基である)で表されるオルガノシランからなる群から選択される、紫外線硬化性官能基を分子中に1個有するオルガノポリシロキサン及び/又はオルガノシランである、請求項6に記載の紫外線硬化性組成物。 - 組成物中の成分(S1)のオルガノポリシロキサン及び成分(S2)(A)の紫外線硬化性官能基を有し且つケイ素原子を有する化合物が、下記式(3):
平均単位式:
(R3SiO1/2)e(R2SiO2/2)f(RSiO3/2)g(SiO4/2)h (4)
(式(4)中、Rは、それぞれ独立に、紫外線硬化性官能基及び非置換又はフッ素で置換された一価炭化水素基から選ばれる基であり、全てのRのうち、少なくとも2個は紫外線硬化性官能基であり、(g+h)は正数であり、eは0又は正数であり、fは0~20の範囲内の数である。)
で表されるオルガノポリシロキサン、
下記式(5):
及びそれらから任意に選択される2種以上のオルガノポリシロキサンの混合物からなる群から選択される、紫外線硬化性官能基を有する1種類以上のオルガノポリシロキサンである、請求項7に記載の紫外線硬化性組成物。 - 組成物中の成分(S1)及び成分(S2)(A)の化合物の紫外線硬化性官能基の数が、一分子当たり平均して2個である、請求項7又は9に記載の紫外線硬化性組成物。
- 組成物中の成分(S1)及び成分(S2)(A)の化合物が、紫外線硬化性官能基を分子中に1個有するオルガノポリシロキサンである、請求項6又は8に記載の紫外線硬化性組成物。
- 組成物中の成分(S1)及び成分(S2)(A)の化合物の紫外線硬化性官能基がアクリロキシ基含有基、メタクリロキシ基含有基、エポキシ基含有基、オキセタン基含有基、及びビニルエーテル基含有基からなる群から選ばれる官能基である、請求項1~11のいずれか1項に記載の紫外線硬化性組成物。
- 成分(S)として成分(S1)を含む、請求項1~12のいずれか一項に記載の紫外線硬化性組成物。
- 成分(S)として成分(S2)を含む、請求項1~12のいずれか一項に記載の紫外線硬化性組成物。
- 成分(S1)を含み、成分(S1)がエポキシ官能性ポリシロキサンである、請求項13に記載の紫外線硬化性組成物。
- 成分(S2)を含み、成分(A)がアクリロキシ基を有する化合物である、請求項14に記載の紫外線硬化性組成物。
- 成分(S2)を含み、成分(A)がアクリロキシ基を有する化合物であり、成分(B)がアルケニル基を有するオルガノポリシロキサンである、請求項16に記載の紫外線硬化性組成物。
- 成分(S2)を含み、成分(A)がケイ素原子を有しない化合物である、請求項14、16、及び17のいずれか一項に記載の紫外線硬化性組成物。
- 成分(S2)を含み、成分(A)がケイ素原子を有する化合物である、請求項14、16、及び17のいずれか一項に記載の紫外線硬化性組成物。
- 成分(S1)を含み、成分(S1)が、
(S1-1)一分子中に平均して2個以上のエポキシ基含有基を有する1種以上のオルガノポリシロキサン、及び
(S1-2)一分子中に1個のエポキシ基含有基を有するオルガノポリシロキサン及び/又はオルガノシランからなる群から選択される1種以上の有機ケイ素化合物を、
成分(S1-1)及び成分(S1-2)が100/0~0/100(S1-1/S1-2)となる質量比で含む混合物である、請求項15に記載の紫外線硬化性組成物。 - 成分(S1)を含み、成分(S1)が、(S1-2-1)1,1,1,3,5,5,5-ヘプタメチル-3-[2-(3,4-エポキシシクロヘキシル)エチル]トリシロキサンであるか、又は(S1-2-1)1,1,1,3,5,5,5-ヘプタメチル-3-[2-(3,4-エポキシシクロヘキシル)エチル]トリシロキサンと、以下の(S1-1-1)の群から選ばれる少なくとも一種の化合物との混合物であり、その質量比が100/0~0/100(S-2-1の量/S1-1-1の群から選択される化合物の総量)の範囲である、請求項20に記載の紫外線硬化性組成物:
(S1-1-1):
1,3-ビス[2-(3,4-エポキシシクロヘキシル)エチル]-1,1,3,3-テトラメチルジシロキサン、1,5-ビス[2-(3,4-エポキシシクロヘキシル)エチル]-1,1,3,3,5,5-ヘキサメチルトリシロキサン、1,1,3,3,5,5,7,7,9,9-デカメチル-1,9-ビス[2-(3,4-エポキシシクロヘキシル)エチル]ペンタシロキサン、メチル(トリス[2-(3,4-エポキシシクロヘキシル)エチル]ジメチルシロキシ)シラン、テトラキス([2-(3,4-エポキシシクロヘキシル)エチル]ジメチルシロキシ)シラン、1,3,5,7-テトラメチル-1,3,5,7-テトラ[2-(3,4-エポキシシクロヘキシル)エチル]-シクロテトラシロキサン、1,3-ビス(3-グリシドキシプロピル)-1,1,3,3-テトラメチルジシロキサン、1,5-ビス(3-グリシドキシプロピル)-1,1,3,3,5,5-ヘキサメチルトリシロキサン、1,1,3,3,5,5,7,7,9,9-デカメチル-1,9-ビス(3-グリシドキシプロピル)ペンタシロキサンメチル[トリス(3-グリシドキシプロピル)ジメチルシロキシ]シラン、テトラキス[(3-グリシドキシプロピル)ジメチルシロキシ]シラン、1,3,5,7-テトラメチル-1,3,5,7-テトラ(3-グリシドキシプロピル)-シクロテトラシロキサン。 - 成分(S2)を含み、組成物中の成分(A)が、アクリロキシ基を1個有する化合物またはアクリロキシ基を1個有する二種以上の化合物の混合物である、請求項16~19のいずれか一項に記載の紫外線硬化性組成物。
- 成分(S2)を含み、組成物中の成分(A)が、アクリロキシ基を1個有する一種以上の化合物とアクリロキシ基を2個以上有する一種以上の化合物の混合物である、請求項16~19のいずれか一項に記載の紫外線硬化性組成物。
- 成分(S2)を含み、組成物中の成分(A)が、1個以上のアクリロキシ基を有し且つケイ素原子を有しない化合物である、請求項16~18のいずれか一項に記載の紫外線硬化性組成物。
- 成分(S2)を含み、組成物中の成分(B)が下記成分(B1)及び(B2):
(B1)一分子中に3個以上のアルケニル基を有し、紫外線硬化性官能基を有しないオルガノポリシロキサン
(B2)一分子中に2個以上のアルケニル基を有し、ビニル基の含有率が5質量%以上であり、かつ紫外線硬化性官能基を有しないオルガノポリシロキサン、
からなる群から選択される一種以上の成分である、請求項14、16、17、18、19、22、23、及び24のいずれか1項に記載の紫外線硬化性組成物。 - 成分(S2)を含み、組成物中の成分(B)が、平均組成式:
RaR’bSiO(4-a―b)/2 (7)
(式(7)中、Rは、アルケニル基であり、
R’は、アルケニル基を除く一価炭化水素基、水酸基、及びアルコキシ基から選ばれる基であり、
a及びbは次の条件:1≦a+b<3及び0.1≦a/(a+b)≦1.0を満たす数であり、分子中に少なくとも2個のRを有する。)
で表される直鎖状、分岐状、又は環状のオルガノポリシロキサンである、請求項14、16、17、18、19、22、23、及び24のいずれか1項に記載の紫外線硬化性組成物。 - 成分(S2)を含み、組成物中の成分(B)のオルガノポリシロキサンが、下記式(8):
平均単位式:
(R3SiO1/2)e(R2SiO2/2)f(RSiO3/2)g(SiO4/2)h (9)
(式(9)中、Rは、それぞれ独立に、アルケニル基及び非置換又はフッ素で置換された一価炭化水素基から選ばれる基であり、全てのRのうち、少なくとも2個はアルケニル基であり、(g+h)は正数であり、eは0又は正数であり、fは0~100の範囲内の数である。)で表されるオルガノポリシロキサン、
下記式(10):
及びこれらのオルガノポリシロキサンの混合物からなる群から選択される、分子内にアルケニル基を2個以上有する1種類以上のオルガノポリシロキサンである、請求項14、16、17、18、19、20、22、23、及び24のいずれか一項に記載の紫外線硬化性組成物。 - 成分(S2)を含み、組成物中の成分(B)が、(RSiO3/2)単位を有するオルガノポリシロキサンを含む、請求項25又は26に記載の紫外線硬化性組成物。
- 成分(S2)を含み、組成物中の成分(B)が、一分子中に3個以上のアルケニル基を有するオルガノポリシロキサンである、請求項25~28のいずれか1項に記載の紫外線硬化性組成物。
- 成分(S2)を含み、組成物中の成分(B)のアルケニル基が、炭素数3~8のアルケニル基である、請求項25~29のいずれか1項に記載の紫外線硬化性組成物。
- E型粘度計を用いて25℃で測定した組成物全体の粘度が5~60mPa・sの範囲である、請求項1~30のいずれか1項に記載の紫外線硬化性組成物。
- E型粘度計を用いて25℃で測定した組成物全体の粘度が5~30mPa・sの範囲である、請求項1~30のいずれか1項に記載の紫外線硬化性組成物。
- 厚さ10μmの硬化物の、波長域360~405nmにおける光透過率の最も低い値が25%以下である、請求項1~32のいずれか1項に記載の紫外線硬化性組成物。
- 厚さ10μmの硬化物の、波長域360~405nmにおける光透過率の最も低い値が10%以下である、請求項1~32のいずれか1項に記載の紫外線硬化性組成物。
- 請求項1~34のいずれか1項に記載の紫外線硬化性組成物を含む、絶縁性コーティング剤。
- 請求項1~34のいずれか1項に記載の紫外線硬化性組成物の硬化物。
- 請求項1~34のいずれか1項に記載の紫外線硬化性組成物の硬化物を絶縁性コーティング層として使用する方法。
- 請求項1~34のいずれか1項に記載の紫外線硬化性組成物の硬化物からなる層を含む表示装置。
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202280027655.0A CN117203280A (zh) | 2021-03-26 | 2022-03-25 | 紫外线固化性组合物及其用途 |
KR1020237036882A KR20230162055A (ko) | 2021-03-26 | 2022-03-25 | 자외선 경화성 조성물 및 그의 용도 |
JP2023509327A JPWO2022203042A1 (ja) | 2021-03-26 | 2022-03-25 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2021-053363 | 2021-03-26 | ||
JP2021053363 | 2021-03-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2022203042A1 true WO2022203042A1 (ja) | 2022-09-29 |
Family
ID=83397471
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2022/014393 WO2022203042A1 (ja) | 2021-03-26 | 2022-03-25 | 紫外線硬化性組成物及びその用途 |
Country Status (4)
Country | Link |
---|---|
JP (1) | JPWO2022203042A1 (ja) |
KR (1) | KR20230162055A (ja) |
CN (1) | CN117203280A (ja) |
WO (1) | WO2022203042A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2024071133A1 (ja) * | 2022-09-27 | 2024-04-04 | ダウ・東レ株式会社 | 紫外線硬化性組成物およびその用途 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2018095696A (ja) * | 2016-12-09 | 2018-06-21 | 株式会社リコー | 活性エネルギー線硬化型組成物、活性エネルギー線硬化型インク、組成物収容容器、像形成装置、像形成方法、及び硬化物 |
WO2018199305A1 (ja) * | 2017-04-28 | 2018-11-01 | 日産化学株式会社 | 反応性シルセスキオキサン化合物を含む光導波路形成用組成物 |
CN110894361A (zh) * | 2019-12-12 | 2020-03-20 | 浙江福斯特新材料研究院有限公司 | 光固化封装组合物、封装结构及半导体器件 |
WO2020090346A1 (ja) * | 2018-10-30 | 2020-05-07 | ダウ・東レ株式会社 | 紫外線硬化性オルガノポリシロキサン組成物およびその用途 |
JP2020083987A (ja) * | 2018-11-21 | 2020-06-04 | 株式会社ダイセル | ガラス代替基材用耐候性ハードコート組成物、硬化物、及び積層体 |
JP2020139108A (ja) * | 2019-03-01 | 2020-09-03 | 日東電工株式会社 | 有機el表示装置用粘着剤組成物、有機el表示装置用粘着剤層、有機el表示装置用粘着剤層付き偏光フィルム、及び有機el表示装置 |
JP2021038386A (ja) * | 2019-08-28 | 2021-03-11 | 荒川化学工業株式会社 | 活性エネルギー線硬化型防眩性ハードコート剤、硬化膜、及び積層フィルム |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6727370B2 (ja) | 2019-04-15 | 2020-07-22 | 日東電工株式会社 | 紫外線硬化型アクリル系粘着剤組成物、紫外線硬化型アクリル系粘着剤層、粘着剤層付き偏光フィルム、紫外線硬化型アクリル系粘着剤層の製造方法、及び画像表示装置 |
JP6729776B1 (ja) | 2019-04-25 | 2020-07-22 | 東洋インキScホールディングス株式会社 | 紫外線吸収材料、およびその組成物 |
-
2022
- 2022-03-25 KR KR1020237036882A patent/KR20230162055A/ko unknown
- 2022-03-25 JP JP2023509327A patent/JPWO2022203042A1/ja active Pending
- 2022-03-25 WO PCT/JP2022/014393 patent/WO2022203042A1/ja active Application Filing
- 2022-03-25 CN CN202280027655.0A patent/CN117203280A/zh active Pending
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2018095696A (ja) * | 2016-12-09 | 2018-06-21 | 株式会社リコー | 活性エネルギー線硬化型組成物、活性エネルギー線硬化型インク、組成物収容容器、像形成装置、像形成方法、及び硬化物 |
WO2018199305A1 (ja) * | 2017-04-28 | 2018-11-01 | 日産化学株式会社 | 反応性シルセスキオキサン化合物を含む光導波路形成用組成物 |
WO2020090346A1 (ja) * | 2018-10-30 | 2020-05-07 | ダウ・東レ株式会社 | 紫外線硬化性オルガノポリシロキサン組成物およびその用途 |
JP2020083987A (ja) * | 2018-11-21 | 2020-06-04 | 株式会社ダイセル | ガラス代替基材用耐候性ハードコート組成物、硬化物、及び積層体 |
JP2020139108A (ja) * | 2019-03-01 | 2020-09-03 | 日東電工株式会社 | 有機el表示装置用粘着剤組成物、有機el表示装置用粘着剤層、有機el表示装置用粘着剤層付き偏光フィルム、及び有機el表示装置 |
JP2021038386A (ja) * | 2019-08-28 | 2021-03-11 | 荒川化学工業株式会社 | 活性エネルギー線硬化型防眩性ハードコート剤、硬化膜、及び積層フィルム |
CN110894361A (zh) * | 2019-12-12 | 2020-03-20 | 浙江福斯特新材料研究院有限公司 | 光固化封装组合物、封装结构及半导体器件 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2024071133A1 (ja) * | 2022-09-27 | 2024-04-04 | ダウ・東レ株式会社 | 紫外線硬化性組成物およびその用途 |
Also Published As
Publication number | Publication date |
---|---|
JPWO2022203042A1 (ja) | 2022-09-29 |
KR20230162055A (ko) | 2023-11-28 |
CN117203280A (zh) | 2023-12-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN114616299B (zh) | 紫外线固化性聚有机硅氧烷组合物及其用途 | |
JP5771148B2 (ja) | 硬化成型体の製造方法及び硬化成型体 | |
WO2020090346A1 (ja) | 紫外線硬化性オルガノポリシロキサン組成物およびその用途 | |
US20230107203A1 (en) | Solventless photocurable liquid composition, cured product thereof, optical filler containing same, and display device including layer comprising said cured product | |
WO2022203042A1 (ja) | 紫外線硬化性組成物及びその用途 | |
WO2022202498A1 (ja) | 紫外線硬化性組成物およびその用途 | |
JP4439017B2 (ja) | 成型体用硬化性樹脂組成物、成型体及びその製造方法 | |
WO2022202499A1 (ja) | 紫外線硬化性組成物およびその用途 | |
WO2022102626A1 (ja) | 紫外線硬化性組成物およびその用途 | |
CN112752822B (zh) | 紫外线固化型有机硅粘接剂组合物和层叠体的制造方法 | |
JP7485496B2 (ja) | 硬化性シリコーン組成物およびその用途 | |
WO2022234802A1 (ja) | 紫外線硬化性シリコーン組成物及びその硬化物、積層体、並びに光学装置又は光学ディスプレイ | |
KR20230106638A (ko) | 자외선 경화성 오가노폴리실록산 조성물 및 그의 용도 | |
WO2023224118A1 (ja) | 紫外線硬化性組成物およびその用途 | |
WO2023037941A1 (ja) | 高エネルギー線硬化性組成物およびその用途 | |
WO2024063068A1 (ja) | 紫外線硬化性組成物およびその用途 | |
WO2024063069A1 (ja) | 紫外線硬化性組成物およびその用途 | |
KR20240052977A (ko) | 고에너지선 경화성 조성물 및 그의 용도 | |
WO2024071133A1 (ja) | 紫外線硬化性組成物およびその用途 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 22775823 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2023509327 Country of ref document: JP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 202280027655.0 Country of ref document: CN |
|
ENP | Entry into the national phase |
Ref document number: 20237036882 Country of ref document: KR Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 18283294 Country of ref document: US |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 22775823 Country of ref document: EP Kind code of ref document: A1 |