JP2005194474A - Curable resin composition for optical recording medium and optical recording medium - Google Patents
Curable resin composition for optical recording medium and optical recording medium Download PDFInfo
- Publication number
- JP2005194474A JP2005194474A JP2004004481A JP2004004481A JP2005194474A JP 2005194474 A JP2005194474 A JP 2005194474A JP 2004004481 A JP2004004481 A JP 2004004481A JP 2004004481 A JP2004004481 A JP 2004004481A JP 2005194474 A JP2005194474 A JP 2005194474A
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- JP
- Japan
- Prior art keywords
- optical recording
- composition
- platinum
- group
- mass
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 230000003287 optical effect Effects 0.000 title claims abstract description 30
- 239000011342 resin composition Substances 0.000 title claims abstract description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 57
- 239000000203 mixture Substances 0.000 claims abstract description 50
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 39
- 239000003054 catalyst Substances 0.000 claims abstract description 29
- 229910052751 metal Inorganic materials 0.000 claims abstract description 17
- 239000002184 metal Substances 0.000 claims abstract description 17
- 239000000758 substrate Substances 0.000 claims abstract description 17
- 229920006136 organohydrogenpolysiloxane Polymers 0.000 claims abstract description 13
- 230000001681 protective effect Effects 0.000 claims abstract description 9
- 230000003197 catalytic effect Effects 0.000 claims abstract description 7
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
- 229920003023 plastic Polymers 0.000 claims abstract description 5
- 239000004033 plastic Substances 0.000 claims abstract description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 4
- -1 platinum group metal compound Chemical class 0.000 claims description 29
- 239000010410 layer Substances 0.000 claims description 27
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 229910052697 platinum Inorganic materials 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 9
- 239000003504 photosensitizing agent Substances 0.000 claims description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000011241 protective layer Substances 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 238000005452 bending Methods 0.000 abstract 1
- 230000008602 contraction Effects 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- FALJXSPLMPMHEL-UHFFFAOYSA-N C[Pt](C)C Chemical compound C[Pt](C)C FALJXSPLMPMHEL-UHFFFAOYSA-N 0.000 description 22
- 238000000034 method Methods 0.000 description 20
- 238000001723 curing Methods 0.000 description 17
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 15
- 238000007259 addition reaction Methods 0.000 description 12
- 238000004528 spin coating Methods 0.000 description 10
- 230000005540 biological transmission Effects 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 229920002554 vinyl polymer Polymers 0.000 description 9
- 239000000463 material Substances 0.000 description 7
- 229920000515 polycarbonate Polymers 0.000 description 7
- 239000004417 polycarbonate Substances 0.000 description 7
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- URHURAUXXZJQAP-UHFFFAOYSA-N C=1C=CC=CC=1[Pt]C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1[Pt]C1=CC=CC=C1 URHURAUXXZJQAP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000007809 chemical reaction catalyst Substances 0.000 description 5
- 238000013329 compounding Methods 0.000 description 5
- 239000004205 dimethyl polysiloxane Substances 0.000 description 5
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 238000006459 hydrosilylation reaction Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 5
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 5
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 230000005484 gravity Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 238000013007 heat curing Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920002050 silicone resin Polymers 0.000 description 3
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 2
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- 229910004283 SiO 4 Inorganic materials 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- KDUIUFJBNGTBMD-DLMDZQPMSA-N [8]annulene Chemical compound C/1=C/C=C\C=C/C=C\1 KDUIUFJBNGTBMD-DLMDZQPMSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000005604 azodicarboxylate group Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 230000036211 photosensitivity Effects 0.000 description 2
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- 230000001846 repelling effect Effects 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- VMFJVWPCRCAWBS-UHFFFAOYSA-N (3-methoxyphenyl)-phenylmethanone Chemical compound COC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 VMFJVWPCRCAWBS-UHFFFAOYSA-N 0.000 description 1
- SWFHGTMLYIBPPA-UHFFFAOYSA-N (4-methoxyphenyl)-phenylmethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 SWFHGTMLYIBPPA-UHFFFAOYSA-N 0.000 description 1
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 description 1
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical group C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 1
- VWMJKATZBMZSMO-UHFFFAOYSA-N 1,2,3,4,5-pentafluorobenzene-6-ide;platinum(2+) Chemical compound [Pt+2].FC1=[C-]C(F)=C(F)C(F)=C1F.FC1=[C-]C(F)=C(F)C(F)=C1F VWMJKATZBMZSMO-UHFFFAOYSA-N 0.000 description 1
- SKBBQSLSGRSQAJ-UHFFFAOYSA-N 1-(4-acetylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C(C)=O)C=C1 SKBBQSLSGRSQAJ-UHFFFAOYSA-N 0.000 description 1
- HDMHXSCNTJQYOS-UHFFFAOYSA-N 1-(4-prop-2-enylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(CC=C)C=C1 HDMHXSCNTJQYOS-UHFFFAOYSA-N 0.000 description 1
- YRAJNWYBUCUFBD-UHFFFAOYSA-N 2,2,6,6-tetramethylheptane-3,5-dione Chemical compound CC(C)(C)C(=O)CC(=O)C(C)(C)C YRAJNWYBUCUFBD-UHFFFAOYSA-N 0.000 description 1
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical group C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-UHFFFAOYSA-N 0.000 description 1
- KFBXUKHERGLHLG-UHFFFAOYSA-N 2,4-Nonanedione Chemical compound CCCCCC(=O)CC(C)=O KFBXUKHERGLHLG-UHFFFAOYSA-N 0.000 description 1
- ZYXNLVMBIHVDRH-UHFFFAOYSA-N 2-Methylpropyl 3-oxobutanoate Chemical compound CC(C)COC(=O)CC(C)=O ZYXNLVMBIHVDRH-UHFFFAOYSA-N 0.000 description 1
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-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
- 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
- LEUJIOLEGDAICX-UHFFFAOYSA-N 3-chloroxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=C(Cl)C=C3OC2=C1 LEUJIOLEGDAICX-UHFFFAOYSA-N 0.000 description 1
- KMSYDDGPKBBSNA-UHFFFAOYSA-N 3-ethyl-1-phenylpentan-1-one Chemical compound CCC(CC)CC(=O)C1=CC=CC=C1 KMSYDDGPKBBSNA-UHFFFAOYSA-N 0.000 description 1
- QYXVDGZUXHFXTO-UHFFFAOYSA-L 3-oxobutanoate;platinum(2+) Chemical compound [Pt+2].CC(=O)CC([O-])=O.CC(=O)CC([O-])=O QYXVDGZUXHFXTO-UHFFFAOYSA-L 0.000 description 1
- 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 1
- PQCLJXVUAWLNSV-UHFFFAOYSA-N 5-Methyl-2,3-hexanedione Chemical compound CC(C)CC(=O)C(C)=O PQCLJXVUAWLNSV-UHFFFAOYSA-N 0.000 description 1
- HLAIQVYIYWIDDJ-UHFFFAOYSA-N BrC1=CC=C(C=C1)[Pt]C1=CC=C(C=C1)Br Chemical compound BrC1=CC=C(C=C1)[Pt]C1=CC=C(C=C1)Br HLAIQVYIYWIDDJ-UHFFFAOYSA-N 0.000 description 1
- REIYHFWZISXFKU-UHFFFAOYSA-N Butyl acetoacetate Chemical compound CCCCOC(=O)CC(C)=O REIYHFWZISXFKU-UHFFFAOYSA-N 0.000 description 1
- MIAUYHGLMNACGF-UHFFFAOYSA-N C(C)(=O)C1=CC=C(C=C1)[Pt]C1=CC=C(C=C1)C(C)=O Chemical compound C(C)(=O)C1=CC=C(C=C1)[Pt]C1=CC=C(C=C1)C(C)=O MIAUYHGLMNACGF-UHFFFAOYSA-N 0.000 description 1
- NZYSQTRFLJKIHY-UHFFFAOYSA-N C(C)[Pt](C)CC Chemical compound C(C)[Pt](C)CC NZYSQTRFLJKIHY-UHFFFAOYSA-N 0.000 description 1
- QTZBUMQAAGVMBG-UHFFFAOYSA-N C(C=C)(=O)[Pt](C)C Chemical compound C(C=C)(=O)[Pt](C)C QTZBUMQAAGVMBG-UHFFFAOYSA-N 0.000 description 1
- AJABOQBJFSEDSK-UHFFFAOYSA-N C(CCCCCCCCCCC)(=O)[Pt](C)C Chemical compound C(CCCCCCCCCCC)(=O)[Pt](C)C AJABOQBJFSEDSK-UHFFFAOYSA-N 0.000 description 1
- NKTIPKOZMQGNMQ-UHFFFAOYSA-N C1(=CC=C(C=C1)[Pt]C1=CC=C(C=C1)C)C Chemical compound C1(=CC=C(C=C1)[Pt]C1=CC=C(C=C1)C)C NKTIPKOZMQGNMQ-UHFFFAOYSA-N 0.000 description 1
- ZWDGEUHPUCSPKM-UHFFFAOYSA-N C1(=CC=CC2=CC=CC=C12)[Pt]C1=CC=CC2=CC=CC=C12 Chemical compound C1(=CC=CC2=CC=CC=C12)[Pt]C1=CC=CC2=CC=CC=C12 ZWDGEUHPUCSPKM-UHFFFAOYSA-N 0.000 description 1
- CINPOXZQHAIFFP-UHFFFAOYSA-N C1(CCCC1)[Pt](C1CCCC1)C1CCCC1 Chemical compound C1(CCCC1)[Pt](C1CCCC1)C1CCCC1 CINPOXZQHAIFFP-UHFFFAOYSA-N 0.000 description 1
- ZFJQZDBSZBPSDR-UHFFFAOYSA-N C1(CCCCC1)[Pt](C1CCCCC1)C1CCCCC1 Chemical compound C1(CCCCC1)[Pt](C1CCCCC1)C1CCCCC1 ZFJQZDBSZBPSDR-UHFFFAOYSA-N 0.000 description 1
- SKXDTDZMAPISOK-UHFFFAOYSA-N CC1=C(C=CC=C1)[Pt]C1=C(C=CC=C1)C Chemical compound CC1=C(C=CC=C1)[Pt]C1=C(C=CC=C1)C SKXDTDZMAPISOK-UHFFFAOYSA-N 0.000 description 1
- IREDFZSJSDSZTC-UHFFFAOYSA-N CCCCCC[Pt](CCCCCC)CCCCCC Chemical compound CCCCCC[Pt](CCCCCC)CCCCCC IREDFZSJSDSZTC-UHFFFAOYSA-N 0.000 description 1
- GUBRRQRTCOELEI-UHFFFAOYSA-N CC[Pt](C)C Chemical compound CC[Pt](C)C GUBRRQRTCOELEI-UHFFFAOYSA-N 0.000 description 1
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- JAMFRFUMJYPQAD-UHFFFAOYSA-N CN(C)c1ccc([Pt]c2ccc(cc2)N(C)C)cc1 Chemical compound CN(C)c1ccc([Pt]c2ccc(cc2)N(C)C)cc1 JAMFRFUMJYPQAD-UHFFFAOYSA-N 0.000 description 1
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- VNHZUQBHRUURNX-UHFFFAOYSA-N C[Pt](C)C(C)=O Chemical compound C[Pt](C)C(C)=O VNHZUQBHRUURNX-UHFFFAOYSA-N 0.000 description 1
- HUEACPHXGDZAMI-UHFFFAOYSA-N C[Pt](CC1=CC=CC=C1)C Chemical compound C[Pt](CC1=CC=CC=C1)C HUEACPHXGDZAMI-UHFFFAOYSA-N 0.000 description 1
- OELSXEOEZJJCNH-UHFFFAOYSA-N C[Si](C)(C)C(C=C1)=CC=C1[Pt]C(C=C1)=CC=C1[Si](C)(C)C Chemical compound C[Si](C)(C)C(C=C1)=CC=C1[Pt]C(C=C1)=CC=C1[Si](C)(C)C OELSXEOEZJJCNH-UHFFFAOYSA-N 0.000 description 1
- YBOLPSRXMOIGST-UHFFFAOYSA-N C[Si](C)(C)OC(C=C1)=CC=C1[Pt]C(C=C1)=CC=C1O[Si](C)(C)C Chemical compound C[Si](C)(C)OC(C=C1)=CC=C1[Pt]C(C=C1)=CC=C1O[Si](C)(C)C YBOLPSRXMOIGST-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DTYPSLBQPZVPET-UHFFFAOYSA-N ClC=1C=C(C=CC=1)[Pt]C1=CC(=CC=C1)Cl Chemical compound ClC=1C=C(C=CC=1)[Pt]C1=CC(=CC=C1)Cl DTYPSLBQPZVPET-UHFFFAOYSA-N 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- SYFQNCZCTMLSML-UHFFFAOYSA-N FC(C(C=CC=C1)=C1[Pt]C1=C(C(F)(F)F)C=CC=C1)(F)F Chemical compound FC(C(C=CC=C1)=C1[Pt]C1=C(C(F)(F)F)C=CC=C1)(F)F SYFQNCZCTMLSML-UHFFFAOYSA-N 0.000 description 1
- OGWPVQZTQAIXNA-UHFFFAOYSA-N FC(C1=CC=C(C=C1)[Pt]C1=CC=C(C=C1)C(F)(F)F)(F)F Chemical compound FC(C1=CC=C(C=C1)[Pt]C1=CC=C(C=C1)C(F)(F)F)(F)F OGWPVQZTQAIXNA-UHFFFAOYSA-N 0.000 description 1
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- AYXMOPBXBPQFGE-UHFFFAOYSA-N FC(C=C1F)=CC(F)=C1[Pt]C(C(F)=CC(F)=C1)=C1F Chemical compound FC(C=C1F)=CC(F)=C1[Pt]C(C(F)=CC(F)=C1)=C1F AYXMOPBXBPQFGE-UHFFFAOYSA-N 0.000 description 1
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- 239000004793 Polystyrene Substances 0.000 description 1
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- 125000005595 acetylacetonate group Chemical group 0.000 description 1
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- 125000003277 amino group Chemical group 0.000 description 1
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- 238000010828 elution Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
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- 238000011156 evaluation Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
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- 125000005843 halogen group Chemical group 0.000 description 1
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
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- 238000007733 ion plating Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- FSPSELPMWGWDRY-UHFFFAOYSA-N m-Methylacetophenone Chemical compound CC(=O)C1=CC=CC(C)=C1 FSPSELPMWGWDRY-UHFFFAOYSA-N 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- GJYXGIIWJFZCLN-UHFFFAOYSA-N octane-2,4-dione Chemical compound CCCCC(=O)CC(C)=O GJYXGIIWJFZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
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- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- PXXKQOPKNFECSZ-UHFFFAOYSA-N platinum rhodium Chemical group [Rh].[Pt] PXXKQOPKNFECSZ-UHFFFAOYSA-N 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
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- 150000003254 radicals Chemical class 0.000 description 1
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- 229910052703 rhodium Inorganic materials 0.000 description 1
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- 238000004904 shortening Methods 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 229920006268 silicone film Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical compound [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
Abstract
Description
本発明は、レーザー光を用いてデジタル情報を記録する光記録媒体において、硬化前後での体積収縮の少ない液状硬化性樹脂組成物を塗工、硬化させることにより、光透過性の層を形成する際に好適な組成物、及びその組成物を用いて光透過層を形成した光記録媒体に関する。 The present invention forms a light-transmitting layer by applying and curing a liquid curable resin composition having a small volume shrinkage before and after curing in an optical recording medium for recording digital information using a laser beam. In particular, the present invention relates to a suitable composition and an optical recording medium in which a light transmission layer is formed using the composition.
近年、コンピューター、家庭向けの高画質テレビ放送、デジタルカメラ等の普及により、音楽、画像、映像などの膨大なデジタル情報を長期間保存するための媒体が必要になってきた。光記録媒体は、このような大容量のデータを高密度に記録させることができる技術として、急速に発展している。光記録媒体は、用途、方式によって容量や記録・再生システムが異なるが、主流になりつつあるのは、ＣＤ、ＤＶＤに代表されるレーザー光の反射率の差を利用したデータ記録方式である。媒体の構造、データ記録層の材料などは、使用されるレーザー光の波長や、一回書き込み型か、リライタブル型かによっても異なるが、いずれにしても光ディスク量産技術の進歩によって安価に入手できるようになった。 In recent years, with the spread of computers, high-definition television broadcasts for home use, digital cameras, and the like, a medium for storing enormous digital information such as music, images, and images for a long period of time has become necessary. Optical recording media are rapidly developing as a technology capable of recording such a large volume of data with high density. Optical recording media have different capacities and recording / reproducing systems depending on the application and method, but what is becoming mainstream is a data recording method that uses a difference in reflectance of laser light represented by CD and DVD. The structure of the medium, the material of the data recording layer, and the like differ depending on the wavelength of the laser beam used and whether it is a once-write type or a rewritable type. Became.
一方、光記録媒体に要求される容量は、用途の拡大に伴って急増している。ことに最近は、デジタル高画質テレビ放送を２時間以上録画できるような、大容量媒体の需要がある。このような高密度記録方式としては、ブルーレイディスクに代表されるように、レーザー光の波長を５００ｎｍ以下と短くし、更に光学レンズの開口数（ＮＡ）を大きくすることが提案されている。例えば波長４０５ｎｍの青色レーザー、開口数０．６０以上のレンズを使用した場合、ディスクの傾きにより発生するコマ収差を低減するため、記録層上に設けられた光透過層を薄くする必要がある。即ち、一般に約１００μｍ程度の一定厚みのカバー層を形成する必要がある。 On the other hand, the capacity required for optical recording media has been increasing rapidly with the expansion of applications. In particular, recently, there is a demand for a large-capacity medium that can record a digital high-definition television broadcast for two hours or more. As such a high-density recording method, as typified by a Blu-ray disc, it has been proposed to shorten the wavelength of laser light to 500 nm or less and further increase the numerical aperture (NA) of the optical lens. For example, when a blue laser having a wavelength of 405 nm and a lens having a numerical aperture of 0.60 or more are used, it is necessary to make the light transmission layer provided on the recording layer thin in order to reduce coma generated by the tilt of the disk. That is, it is generally necessary to form a cover layer having a constant thickness of about 100 μm.
この光透過保護層の形成方法としては、透明シートを接着剤にて貼り合わせる方法や、液状硬化性樹脂組成物を平坦に塗工、硬化させる方法が報告されている。 As a method for forming this light transmission protective layer, a method of bonding a transparent sheet with an adhesive and a method of applying and curing a liquid curable resin composition flatly have been reported.
前者の方法では、透明シートは市販されているものを利用することができるので、材料を新たに開発する必要はない。しかしながら、シートのカットの困難さ、貼り合わせ技術、及びその装置のための投資、生産性の低さなど、デメリットが多い。それに対し、後者の方法は、従来のスピンコート・硬化装置が利用でき、かつ膜形成の生産性が高いなどメリットは多い。しかしながら、光記録媒体用として従来知られているアクリル樹脂等の硬化性樹脂コーティング材を所望の厚みで塗布、硬化した場合、硬化前後での体積収縮が大きく、基板が反り、歪みが生じる問題が発生する。従ってこの光透過層を形成するのに適するような、硬化収縮の少ない、新たな硬化性樹脂コーティング組成物の開発が求められている。 In the former method, a commercially available transparent sheet can be used, so there is no need to newly develop a material. However, there are many disadvantages, such as difficulty in cutting sheets, bonding technology, investment for the apparatus, and low productivity. On the other hand, the latter method has many merits such that a conventional spin coating / curing apparatus can be used and the productivity of film formation is high. However, when a curable resin coating material such as an acrylic resin, which is conventionally known for optical recording media, is applied and cured at a desired thickness, there is a problem that the volume shrinks before and after the curing, the substrate warps, and distortion occurs. Occur. Therefore, development of a new curable resin coating composition with little cure shrinkage suitable for forming this light transmission layer is required.
なお、本発明に関連する公知文献としては、下記のものがある。特開平１０−２８３６８３号公報（特許文献１）では、プラスチック透明シートを紫外線硬化性樹脂を用いて接着させることにより、光透過層を形成する技術が開示されている。特開２００２−１０９７８５号公報（特許文献２）では、光透過層が（メタ）アクリレート化合物を主成分としたラジカル重合性樹脂の硬化膜より形成する技術が開示されている。特開平１１−１９１２４０号公報（特許文献３）では、光透過層が、カチオン重合反応により硬化される光硬化型樹脂より形成される技術が開示されている。また、Ｊｐｎ．Ｊ．Ａｐｐｌ．Ｐｈｙｓ．Ｖｏｌ．３９（２０００） ｐｐ．７７５−７７８ Ｍｉｃｈａｅｌ Ｍ．Ｊ．Ｄｅｃｒｅ ａｎｄ Ｐｉｅｔ Ｈ．Ｇ．Ｍ．Ｖｒｏｍａｎｓ（非特許文献１）では、０．１ｍｍカバー層の上述した２種類の形成方法について詳細な報告がなされている。紫外線硬化性樹脂のスピンコート形成法、及び紫外線硬化性接着剤によるポリカーボネートシート貼り合わせ法の両方の方法によって、光記録媒体として必要な光透過層の厚み制御が可能であることが示されている。 In addition, as a well-known document relevant to this invention, there exist the following. Japanese Patent Laid-Open No. 10-283683 (Patent Document 1) discloses a technique for forming a light transmission layer by bonding a plastic transparent sheet using an ultraviolet curable resin. Japanese Patent Application Laid-Open No. 2002-109785 (Patent Document 2) discloses a technique in which a light transmission layer is formed from a cured film of a radical polymerizable resin whose main component is a (meth) acrylate compound. Japanese Patent Application Laid-Open No. 11-191240 (Patent Document 3) discloses a technique in which a light transmission layer is formed from a photocurable resin that is cured by a cationic polymerization reaction. Jpn. J. et al. Appl. Phys. Vol. 39 (2000) pp. 775-778 Michael M.M. J. et al. Decre and Piet H.M. G. M.M. In Vromans (Non-patent Document 1), a detailed report has been made on the above-described two methods of forming a 0.1 mm cover layer. It has been shown that the thickness of the light-transmitting layer necessary as an optical recording medium can be controlled by both the spin coat formation method of an ultraviolet curable resin and the polycarbonate sheet laminating method using an ultraviolet curable adhesive. .
本発明は、上記事情に鑑みなされたもので、光記録媒体の光透過層を形成するのに適する、硬化前後での体積収縮、基板の反り、歪みのない光記録媒体用硬化性樹脂組成物を提供することを目的とする。 The present invention has been made in view of the above circumstances, and is suitable for forming a light transmission layer of an optical recording medium. The curable resin composition for an optical recording medium is free from volume shrinkage before and after curing, warpage of the substrate, and distortion. The purpose is to provide.
本発明者は、上記目的を達成するため鋭意検討した結果、（Ａ）１分子中に脂肪族不飽和結合を有する置換又は非置換の炭化水素基を少なくとも２個含有するオルガノポリシロキサンを１００質量部、（Ｂ）１分子中にケイ素原子と直接結合した水素原子を少なくとも２個有するオルガノハイドロジェンポリシロキサンを１〜４００質量部、（Ｃ）触媒量の白金族金属系触媒を含有し、光透過性保護膜を形成することができるオルガノポリシロキサン組成物が、体積収縮、基板の反り、歪みのない硬化物を形成でき、光透過層形成に好適であることを見出し、本発明をなすに至った。 As a result of intensive studies to achieve the above object, the present inventor has (A) 100 masses of an organopolysiloxane containing at least two substituted or unsubstituted hydrocarbon groups having an aliphatic unsaturated bond in one molecule. 1 to 400 parts by mass of (B) an organohydrogenpolysiloxane having at least two hydrogen atoms directly bonded to silicon atoms in one molecule, (C) a platinum group metal catalyst in a catalytic amount, It was found that an organopolysiloxane composition capable of forming a transparent protective film can form a cured product free from volume shrinkage, substrate warpage, and distortion, and is suitable for forming a light transmission layer. It came.
従って、本発明は、
（Ａ）１分子中に脂肪族不飽和結合を有する置換又は非置換の炭化水素基を少なくとも２個含有するオルガノポリシロキサン １００質量部
（Ｂ）１分子中にケイ素原子と直接結合した水素原子を少なくとも２個有するオルガノハイドロジェンポリシロキサン １〜４００質量部
（Ｃ）触媒量の白金族金属系触媒
を含有し、光透過性保護膜を形成することを特徴とする光記録媒体用硬化性樹脂組成物、及びプラスチック基板に順次積層された反射層、記録層の上に、上記組成物を塗工後、硬化することにより形成される厚み３００μｍ以下の光透過性透明保護層を有する光記録媒体を提供する。
Therefore, the present invention
(A) Organopolysiloxane containing at least two substituted or unsubstituted hydrocarbon groups having an aliphatic unsaturated bond in one molecule 100 parts by mass (B) A hydrogen atom directly bonded to a silicon atom in one molecule A curable resin composition for optical recording media, comprising at least two organohydrogenpolysiloxanes having a catalytic amount of platinum group metal catalyst of 1 to 400 parts by mass (C) and forming a light-transmitting protective film And an optical recording medium having a light-transmitting transparent protective layer having a thickness of 300 μm or less formed by coating the composition on the reflective layer and the recording layer sequentially laminated on the plastic substrate and then curing the composition. provide.
本発明の光記録媒体用組成物は、以下のような効果を有する。
（１）本発明の組成物は、硬化前後での体積減少率（比重法にて測定）が比較的低く、体積収縮による基板の反りの影響を低減することができる。
（２）本発明の組成物は、他の材料に比べて表面張力が低いためスピンコートにて塗工する際、円周方向へ広がりやすく、平坦性が得られやすい。
（３）硬化後のオルガノポリシロキサン膜は、撥水性に富むため、水分の透過による記録層の腐食・変質を防止することが可能である。
（４）硬化後のオルガノポリシロキサン膜は、適度な硬度を保ちながら、表面滑り性、傷付き防止性を発現する。
The composition for optical recording media of the present invention has the following effects.
(1) The composition of the present invention has a relatively low volume reduction rate (measured by a specific gravity method) before and after curing, and can reduce the influence of warpage of the substrate due to volume shrinkage.
(2) Since the composition of the present invention has a lower surface tension than other materials, it tends to spread in the circumferential direction when applied by spin coating, and flatness is easily obtained.
(3) Since the cured organopolysiloxane film is rich in water repellency, it is possible to prevent corrosion and deterioration of the recording layer due to the permeation of moisture.
(4) The cured organopolysiloxane film exhibits surface slip and scratch resistance while maintaining an appropriate hardness.
（Ａ）オルガノポリシロキサン
本発明のオルガノポリシロキサン（Ａ）は、オルガノハイドロジェンポリシロキサン（Ｂ）が有するＳｉＨ基とヒドロシリル化反応しうる炭素−炭素間不飽和結合を置換基として分子中に２個以上含有するポリシロキサンであればすべて使用できる。脂肪族不飽和結合基の位置は、側鎖でも末端でも構わない。
(A) Organopolysiloxane The organopolysiloxane (A) of the present invention has a carbon-carbon unsaturated bond capable of hydrosilylation reaction with the SiH group of the organohydrogenpolysiloxane (B) as a substituent. Any polysiloxane containing at least one can be used. The position of the aliphatic unsaturated bond group may be a side chain or a terminal.
具体例としては、側鎖及び／又は末端にアルケニル基を２個以上有する直鎖状オルガノポリシロキサン、３官能及び／又は４官能の分岐構造を含んだ分岐状オルガノポリシロキサン、２個の有機基がケイ素原子に結合したシロキサン単位からなる環状オルガノポリシロキサン、及び環状構造を分子内に含む直鎖状又は分岐状オルガノポリシロキサンを列挙することができる。側鎖に脂肪族不飽和結合基が存在していれば末端はトリアルキルシリル基で封鎖されていてもよいし、シラノール基、アルコキシシリル基であってもよい。アルケニル基以外の有機基は、炭素数１〜１２、特に１〜１０のものが好ましく、メチル、エチル、プロピル基等のアルキル基、フェニル基等のアリール基、アミノ基、エポキシ基、フッ素や塩素で一部置換された置換アルキル基、置換アリール基等が使用できる。 Specific examples include a linear organopolysiloxane having two or more alkenyl groups in the side chain and / or terminal, a branched organopolysiloxane containing a trifunctional and / or tetrafunctional branched structure, and two organic groups. And cyclic organopolysiloxanes composed of siloxane units bonded to silicon atoms, and linear or branched organopolysiloxanes containing a cyclic structure in the molecule. If an aliphatic unsaturated bond group is present in the side chain, the end may be blocked with a trialkylsilyl group, or may be a silanol group or an alkoxysilyl group. Organic groups other than alkenyl groups are preferably those having 1 to 12 carbon atoms, particularly 1 to 10 carbon atoms, alkyl groups such as methyl, ethyl and propyl groups, aryl groups such as phenyl groups, amino groups, epoxy groups, fluorine and chlorine. A substituted alkyl group, a substituted aryl group or the like partially substituted with can be used.
このオルガノポリシロキサンはオイル状、ガム状、レジン状であってもよいが２５℃における粘度は、５ｍＰａ・ｓ以上であることが好ましい。上限は特に問わないが、レジン状やガム状の場合は３０％トルエン希釈溶液での回転粘度で、１〜１００，０００ｍＰａ・ｓ程度が好適である。 The organopolysiloxane may be in the form of oil, gum or resin, but the viscosity at 25 ° C. is preferably 5 mPa · s or more. The upper limit is not particularly limited, but in the case of a resin or gum, the rotational viscosity in a 30% toluene diluted solution is preferably about 1 to 100,000 mPa · s.
硬化膜の硬度、塗工性、硬化性を考慮した場合、下記平均組成式（１）で表されるものを含むことが好ましい。この場合、式（１）で表されるものは（Ａ）成分中、３０質量％以上、特に５０質量％以上、とりわけ７０質量％以上であることが好ましい。
ここで、Ｒ1はアルケニル基、Ｒ2は１価炭化水素基、Ｒ3は水素原子又はアルキル基である。具体的なＲ1は、ビニル基、アリル基、ブテニル基、ペンテニル基などの炭素数２〜８のアルケニル基である。Ｒ2の１価炭化水素基としては、炭素数１〜８のものが好ましく、メチル基、エチル基、プロピル基等のアルキル基、ビニル基、アリル基、ブテニル基などのアルケニル基、フェニル基などのアリール基、ベンジル基などのアラルキル基や、これらの基の水素原子の一部又は全部がハロゲン原子で置換された基などが挙げられる。Ｒ3のアルキル基としては、炭素数１〜６のものが挙げられ、中でもメチル基、エチル基、プロピル基等が例示される。 Here, R 1 is an alkenyl group, R 2 is a monovalent hydrocarbon group, and R 3 is a hydrogen atom or an alkyl group. Specific R 1 is an alkenyl group having 2 to 8 carbon atoms such as a vinyl group, an allyl group, a butenyl group, or a pentenyl group. The monovalent hydrocarbon group for R 2 is preferably one having 1 to 8 carbon atoms, such as an alkyl group such as a methyl group, an ethyl group or a propyl group, an alkenyl group such as a vinyl group, an allyl group or a butenyl group, a phenyl group, etc. And an aralkyl group such as an aryl group or a benzyl group, a group in which some or all of the hydrogen atoms of these groups are substituted with a halogen atom, and the like. Examples of the alkyl group for R 3 include those having 1 to 6 carbon atoms, and examples thereof include a methyl group, an ethyl group, and a propyl group.
ｍ、ｎ、ｐ、ｑ、ｒは、このオルガノポリシロキサンの２５℃における粘度が５〜３０，０００ｍＰａ・ｓ、好ましくは１０〜２０，０００ｍＰａ・ｓになるように選定されるが、ｍ、ｑは正数であり、（ｑ＋ｒ）／（ｍ＋ｎ＋ｐ）＝０．１〜２．０、好ましくは０．６〜１．５の範囲にある。この値が０．１未満であると保護膜としての十分な強度が得られなくなり、２．０を超えるとこのオルガノポリシロキサンの合成が困難になるおそれがある。 m, n, p, q and r are selected so that the viscosity of this organopolysiloxane at 25 ° C. is 5 to 30,000 mPa · s, preferably 10 to 20,000 mPa · s. Is a positive number and is in the range of (q + r) / (m + n + p) = 0.1 to 2.0, preferably 0.6 to 1.5. If this value is less than 0.1, sufficient strength as a protective film cannot be obtained, and if it exceeds 2.0, synthesis of this organopolysiloxane may be difficult.
また、ｒ／（ｑ＋ｒ）は０〜０．０５、好ましくは０〜０．０３の範囲である。この値が０．０５を超えると水酸基あるいはアルコキシ基が多くなるため、このシリコーン樹脂組成物の硬化性が低下する。更に、このオルガノポリシロキサンの２５℃における粘度は、上述したように５〜３０，０００ｍＰａ・ｓである。粘度が５ｍＰａ・ｓ未満では硬化性が悪くなる場合があり、３０，０００ｍＰａ・ｓを超えるとシリコーン樹脂組成物の最終粘度が高くなりすぎ、実際の使用に適さなくなるおそれがある。なお、本発明において、粘度は回転粘度計により測定した２５℃における値である。 R / (q + r) is in the range of 0 to 0.05, preferably 0 to 0.03. If this value exceeds 0.05, the number of hydroxyl groups or alkoxy groups increases, and the curability of the silicone resin composition is lowered. Furthermore, the viscosity of this organopolysiloxane at 25 ° C. is 5 to 30,000 mPa · s as described above. If the viscosity is less than 5 mPa · s, the curability may be deteriorated, and if it exceeds 30,000 mPa · s, the final viscosity of the silicone resin composition becomes too high and may not be suitable for actual use. In the present invention, the viscosity is a value at 25 ° C. measured with a rotational viscometer.
なお、アルケニル基の含有量は、オルガノポリシロキサン１００ｇあたりのアルケニル基のモル数で表記した場合、０．０２〜２．０ｍｏｌ／１００ｇ、特に０．０５〜１．２ｍｏｌ／１００ｇとすることが好ましい。アルケニル基が少なすぎると硬化物の架橋点が少なく、硬化性、硬度が低すぎるおそれがあり、また多すぎると架橋点が多すぎて硬化膜にクラックの発生や、膜が脆くなるおそれがある。 The content of the alkenyl group is preferably 0.02 to 2.0 mol / 100 g, particularly 0.05 to 1.2 mol / 100 g when expressed in terms of the number of moles of alkenyl group per 100 g of the organopolysiloxane. . If the number of alkenyl groups is too small, the cured product may have few crosslinking points and the curability and hardness may be too low. If the amount is too large, the number of crosslinking points may be too large and cracks may occur in the cured film or the film may become brittle. .
次に、（Ｂ）成分のオルガノハイドロジェンポリシロキサンは、（Ａ）成分のオルガノポリシロキサンとヒドロシリル化反応により組成物を硬化させる架橋剤として作用するものであり、下記平均組成式（２）
Ｒ4 aＨbＳｉＯ(4-a-b)/2 （２）
（式中、Ｒ4はアルケニル基を除く一価の炭化水素基、ａ、ｂは０．７≦ａ≦２．１、０．００１≦ｂ≦１．０、かつ０．８≦ａ＋ｂ≦２．６、好ましくは０．８≦ａ≦２、０．０１≦ｂ≦１、１≦ａ＋ｂ≦２．４を満たす正数である。）
で示される１分子中に少なくとも２個、好ましくは３個以上のＳｉＨ結合を有し、かつ２５℃での粘度が１，０００ｍＰａ・ｓ以下であるオルガノハイドロジェンポリシロキサンが好ましい。
Next, the organohydrogenpolysiloxane of the component (B) acts as a crosslinking agent for curing the composition by hydrosilylation reaction with the organopolysiloxane of the component (A), and the following average composition formula (2)
R 4 a H b SiO (4-ab) / 2 (2)
(Wherein R 4 is a monovalent hydrocarbon group excluding an alkenyl group, a and b are 0.7 ≦ a ≦ 2.1, 0.001 ≦ b ≦ 1.0, and 0.8 ≦ a + b ≦ 2) .6, preferably 0.8 ≦ a ≦ 2, 0.01 ≦ b ≦ 1, 1 ≦ a + b ≦ 2.4.
An organohydrogenpolysiloxane having at least 2, preferably 3 or more SiH bonds in one molecule and having a viscosity at 25 ° C. of 1,000 mPa · s or less is preferred.
ここで、Ｒ4としては、式（１）中のＲ2と同様の基を挙げることができるが、アルケニル基を有さないものである。また、硬化物の可撓性向上の観点から、フェニル基を含んでいるものが好ましい。 Here, examples of R 4 include the same groups as R 2 in formula (1), but those having no alkenyl group. Moreover, the thing containing a phenyl group from a viewpoint of the flexibility improvement of hardened | cured material is preferable.
上記オルガノハイドロジェンポリシロキサンの末端としては、末端がトリメチルシリル基等のトリオルガノシリル基で封鎖されたシロキサン、ジオルガノハイドロジェンシリル基やジオルガノヒドロキシシリル基で封鎖されたシロキサン等、特に限定されないが、トリメチルシリル基及びジメチルハイドロジェンシリル基で封鎖されたオルガノハイドロジェンポリシロキサン等が好ましい。その例としては、１，１，３，３−テトラメチルジシロキサン、１，３，５，７−テトラメチルシクロテトラシロキサン、両末端トリメチルシリル基封鎖メチルハイドロジェンポリシロキサン、両末端トリメチルシリル基封鎖ジメチルシロキサン・メチルハイドロジェンシロキサン共重合体、両末端ジメチルハイドロジェンシリル基封鎖ジメチルポリシロキサン、両末端ジメチルハイドロジェンシリル基封鎖ジメチルシロキサン・メチルハイドロジェンシロキサン共重合体、両末端トリメチルシリル基封鎖メチルハイドロジェンシロキサン・ジフェニルシロキサン共重合体、両末端トリメチルシリル基封鎖メチルハイドロジェンシロキサン・ジフェニルシロキサン・ジメチルシロキサン共重合体、（ＣＨ3）2ＨＳｉＯ1/2単位とＳｉＯ4/2単位とからなる共重合体、（ＣＨ3）2ＨＳｉＯ1/2単位とＳｉＯ4/2単位と（Ｃ6Ｈ5）ＳｉＯ3/2単位とからなる共重合体などが挙げられる。 The end of the organohydrogenpolysiloxane is not particularly limited, such as a siloxane blocked with a triorganosilyl group such as a trimethylsilyl group or a siloxane blocked with a diorganohydrogensilyl group or a diorganohydroxysilyl group. An organohydrogenpolysiloxane blocked with a trimethylsilyl group and a dimethylhydrogensilyl group is preferred. Examples include 1,1,3,3-tetramethyldisiloxane, 1,3,5,7-tetramethylcyclotetrasiloxane, trimethylsilyl group-capped methylhydrogenpolysiloxane, trimethylsilyl group-capped dimethylsiloxane.・ Methylhydrogensiloxane copolymer, dimethylhydrogensilyl group-capped dimethylpolysiloxane at both ends, dimethylhydrogensilyl group-capped dimethylsiloxane at both ends ・ Methylhydrogensiloxane copolymer, methylhydrogensiloxane capped at both ends with trimethylsilyl group ・diphenylsiloxane copolymers, both end trimethylsilyl groups at methylhydrogensiloxane-diphenylsiloxane-dimethylsiloxane copolymer, (CH 3) 2 HSiO 1/2 units and SiO 4/2 single Copolymers consisting of, like (CH 3) 2 HSiO 1/2 units and the SiO 4/2 units (C 6 H 5) consisting of SiO 3/2 units, and copolymers thereof.
このオルガノハイドロジェンポリシロキサンの分子構造は、直鎖状、環状、分岐状、三次元網状構造のいずれであってもよいが、１分子中のケイ素原子の数（又は重合度）は３〜１，０００、特に３〜３００程度のものを使用することができる。 The molecular structure of the organohydrogenpolysiloxane may be any of linear, cyclic, branched, and three-dimensional network structures, but the number of silicon atoms (or the degree of polymerization) in one molecule is 3 to 1. , Especially about 3 to 300 can be used.
また、このオルガノハイドロジェンポリシロキサンの２５℃における粘度は、１，０００ｍＰａ・ｓ以下、より好ましくは０．１〜５００ｍＰａ・ｓ、更に好ましくは０．５〜３００ｍＰａ・ｓであることが好ましい。 The viscosity of the organohydrogenpolysiloxane at 25 ° C. is 1,000 mPa · s or less, more preferably 0.1 to 500 mPa · s, and still more preferably 0.5 to 300 mPa · s.
上記（Ｂ）成分のオルガノハイドロジェンポリシロキサンの配合量は、（Ａ）成分のオルガノポリシロキサンの総アルケニル基量に依存し、オルガノポリシロキサンの総アルケニル基（モル量）に対してオルガノハイドロジェンポリシロキサンの総ＳｉＨ基（モル量）が０．５〜２．０倍となる量、好ましくは０．８〜１．５倍となる量とすればよい。具体的には、（Ａ）成分のオルガノポリシロキサン１００質量部に対して１〜４００質量部、好ましくは５〜２００質量部である。 The blending amount of the organohydrogenpolysiloxane of the component (B) depends on the total amount of alkenyl groups of the organopolysiloxane of the component (A), and the organohydrogen with respect to the total alkenyl groups (molar amount) of the organopolysiloxane. The total amount of SiH groups (molar amount) of the polysiloxane may be 0.5 to 2.0 times, preferably 0.8 to 1.5 times. Specifically, it is 1 to 400 parts by weight, preferably 5 to 200 parts by weight, based on 100 parts by weight of the organopolysiloxane of component (A).
（Ｃ）成分の白金族金属系触媒は、（Ａ）成分中のアルケニル基と（Ｂ）成分中のＳｉＨ基とのヒドロシリル化付加反応を促進するための触媒であり、この付加反応触媒としては、白金黒、塩化第２白金、塩化白金酸、塩化白金酸と一価アルコールとの反応物、塩化白金酸とオレフィン類との錯体、白金ビスアセトアセテート等の白金系触媒、パラジウム系触媒、ロジウム系触媒などの白金族金属系触媒が挙げられる。なお、この白金族金属系触媒の配合量は触媒量とすることができるが、通常、白金族金属として（Ａ）及び（Ｂ）成分の合計質量に対して１〜５００ｐｐｍ、特に２〜１００ｐｐｍ程度配合することが好ましい。 The component (C) platinum group metal catalyst is a catalyst for promoting the hydrosilylation addition reaction between the alkenyl group in the component (A) and the SiH group in the component (B). , Platinum black, platinous chloride, chloroplatinic acid, reaction product of chloroplatinic acid and monohydric alcohol, complex of chloroplatinic acid and olefins, platinum catalyst such as platinum bisacetoacetate, palladium catalyst, rhodium Platinum group metal catalyst such as a catalyst. In addition, although the compounding quantity of this platinum group metal-type catalyst can be made into a catalyst amount, it is about 1-500 ppm with respect to the total mass of (A) and (B) component as a platinum group metal normally, Especially about 2-100 ppm. It is preferable to mix.
また、（Ｃ）成分の白金族金属系触媒は、（Ａ）成分中のアルケニル基と（Ｂ）成分中のＳｉＨ基とのヒドロシリル化付加反応を光照射によって促進する触媒であることが好ましい。光照射によってヒドロシリル化付加反応を促進する触媒は、紫外線照射による硬化が可能であり、工程時間の短縮、塗膜の平坦性確保が可能となり、また、ＵＶ硬化でありながら、ラジカル重合型に見られる酸素による硬化障害が起きない。このような付加反応触媒としては、以下の３系列がある。
（Ｉ）白金族金属化合物（Ｃ−１）と光増感剤（Ｃ−２）の組合せ
（ＩＩ）白金族金属化合物（Ｃ−１）と光照射にて反応遅延効果が消失する反応制御剤（Ｃ−３）の組合せ
（ＩＩＩ）化合物自体が光感応性を有する白金族金属化合物
The platinum group metal catalyst of component (C) is preferably a catalyst that promotes the hydrosilylation addition reaction between the alkenyl group in component (A) and the SiH group in component (B) by light irradiation. A catalyst that accelerates the hydrosilylation addition reaction by light irradiation can be cured by ultraviolet irradiation, shortening the process time and ensuring the flatness of the coating film. Hardening damage due to oxygen that does not occur. As such an addition reaction catalyst, there are the following three series.
(I) Combination of platinum group metal compound (C-1) and photosensitizer (C-2) (II) Reaction control agent whose reaction delay effect disappears upon irradiation with platinum group metal compound (C-1) Combination (III) of (C-3) Platinum group metal compound in which compound itself has photosensitivity
（Ｉ）における白金族金属化合物（Ｃ−１）及び光増感剤（Ｃ−２）としては、特開昭６２−２１５６５８号公報記載の化合物群が使用できる。白金族金属化合物（Ｃ−１）の具体例としては、白金黒、塩化第２白金、塩化白金酸、塩化白金酸と一価アルコールとの反応物、塩化白金酸とオレフィン類との錯体、白金ビスアセトアセテート等の白金系触媒、パラジウム系触媒、ロジウム系触媒などが挙げられる。また、光増感剤（Ｃ−２）は照射された光を吸収し、（Ｃ−１）を活性化するために添加するものであり、具体的な例としては、アセトフェノン系、ベンゾフェノン系、ベンゾイン系、ベンジル系の誘導体から選択されるものが好適に用いられ、アセトフェノン、プロピオフェノン、ベンゾフェノン、キサントール、フルオレイン、ベンズアルデヒド、アンスラキノン、トリフェニルアミン、カルバゾール、３−メチルアセトフェノン、４−メチルアセトフェノン、３−ペンチルアセトフェノン、４−メトキシアセトフェノン、４−アリルアセトフェノン、ｐ−ジアセチルベンゼン、３−メトキシベンゾフェノン、４−メチルベンゾフェノン、４，４’−ジメトキシベンゾフェノン、３−クロロキサントン、ベンゾイン、ベンゾインメチルエーテル、ベンゾインブチルエーテル、ビス（４−ジメチルアミノフェニル）ケトン、ベンジルメトキシケタール、２−クロロチオキサントンなどが挙げられる。 As the platinum group metal compound (C-1) and photosensitizer (C-2) in (I), the compound group described in JP-A-62-215658 can be used. Specific examples of the platinum group metal compound (C-1) include platinum black, second platinum chloride, chloroplatinic acid, a reaction product of chloroplatinic acid and a monohydric alcohol, a complex of chloroplatinic acid and an olefin, platinum Examples thereof include platinum-based catalysts such as bisacetoacetate, palladium-based catalysts, and rhodium-based catalysts. The photosensitizer (C-2) absorbs irradiated light and is added to activate (C-1). Specific examples include acetophenone series, benzophenone series, Those selected from benzoin and benzyl derivatives are preferably used and include acetophenone, propiophenone, benzophenone, xanthol, fluorin, benzaldehyde, anthraquinone, triphenylamine, carbazole, 3-methylacetophenone, 4-methyl. Acetophenone, 3-pentylacetophenone, 4-methoxyacetophenone, 4-allylacetophenone, p-diacetylbenzene, 3-methoxybenzophenone, 4-methylbenzophenone, 4,4′-dimethoxybenzophenone, 3-chloroxanthone, benzoin, benzoin methyl ester Ether, benzoin butyl ether, bis (4-dimethylaminophenyl) ketone, benzyl methoxy ketal, 2-chlorothioxanthone and the like.
なお、この付加反応触媒の配合量は触媒量とすることができるが、白金族金属化合物（Ｃ−１）は、通常、白金族金属として（Ａ）及び（Ｂ）成分の合計質量に対して１〜５００ｐｐｍ、特に２〜１００ｐｐｍ程度配合することが好ましい。また、光増感剤（Ｃ−２）の配合量としては、（Ａ）成分１００質量部に対し、０．１〜１０質量部であることが好ましく、より好ましくは０．１〜２質量部である。１０質量部を超えると組成物に着色が生じやすくなる場合があり、０．１質量部未満では増感剤としての効果が小さすぎるおそれがある。 In addition, although the compounding quantity of this addition reaction catalyst can be made into a catalytic amount, platinum group metal compound (C-1) is normally with respect to the total mass of (A) and (B) component as a platinum group metal. It is preferable to blend about 1 to 500 ppm, particularly about 2 to 100 ppm. Moreover, as a compounding quantity of a photosensitizer (C-2), it is preferable that it is 0.1-10 mass parts with respect to 100 mass parts of (A) component, More preferably, it is 0.1-2 mass parts. It is. If it exceeds 10 parts by mass, the composition may be easily colored, and if it is less than 0.1 part by mass, the effect as a sensitizer may be too small.
（ＩＩ）における白金族金属化合物（Ｃ−１）及び光照射にて反応遅延効果が消失する反応制御剤（Ｃ−３）としては、米国特許第４６４０９３９号明細書等に記載されているものが利用できる。制御剤（Ｃ−３）は、室温で白金族金属系触媒に作用して付加反応を抑制するが、紫外線照射によって変化して付加反応の抑制効果がなくなるため、組成物が速やかに硬化するものであり、この具体例としては、構造式（３）で表されるアゾジカルボキシレート等が挙げられる。
Ｒ6ＯＯＣ−Ｎ＝Ｎ−ＣＯＯＲ7 （３）
Ｒ6、Ｒ7は同一又は異なる直鎖もしくは分岐した炭素数１〜１２のアルキル基である。より好ましくは、Ｒ6、Ｒ7共にメチル基或いはエチル基であるアゾジカルボキシレートが好ましい。
Examples of the platinum group metal compound (C-1) in (II) and the reaction control agent (C-3) in which the reaction delay effect disappears upon light irradiation include those described in US Pat. No. 4,640,939. Available. The control agent (C-3) acts on the platinum group metal catalyst at room temperature to suppress the addition reaction, but the effect of suppressing the addition reaction is changed by ultraviolet irradiation, so that the composition cures quickly. Specific examples thereof include azodicarboxylate represented by the structural formula (3).
R 6 OOC-N = N- COOR 7 (3)
R 6 and R 7 are the same or different linear or branched alkyl groups having 1 to 12 carbon atoms. More preferably, azodicarboxylate in which both R 6 and R 7 are a methyl group or an ethyl group is preferable.
なお、この付加反応触媒の配合量は触媒量とすることができるが、白金族金属化合物（Ｃ−１）は、通常、白金族金属として（Ａ）及び（Ｂ）成分の合計質量に対して１〜５００ｐｐｍ、特に２〜１００ｐｐｍ程度配合することが好ましい。また、光失活性の反応制御剤（Ｃ−３）の配合量としては、（Ａ）成分１００質量部に対し、０．００１〜１０質量部、特に０．０１〜５質量部が好ましい。制御剤の配合量が少なすぎると光照射前から反応が始まり、液のポットライフが短くなることがあり、多すぎると光照射時に速やかに反応が起こらず、硬化不良となることがある。 In addition, although the compounding quantity of this addition reaction catalyst can be made into a catalytic amount, platinum group metal compound (C-1) is normally with respect to the total mass of (A) and (B) component as a platinum group metal. It is preferable to blend about 1 to 500 ppm, particularly about 2 to 100 ppm. Moreover, as a compounding quantity of the reaction control agent (C-3) of a photodeactivation, 0.001-10 mass parts with respect to 100 mass parts of (A) component, Especially 0.01-5 mass parts is preferable. If the blending amount of the control agent is too small, the reaction starts before the light irradiation and the pot life of the liquid may be shortened. If it is too large, the reaction does not occur quickly at the time of light irradiation and the curing may be poor.
また（ＩＩＩ）のように、付加反応触媒自体が紫外線を吸収し、付加反応活性を示すものを用いることもできる。このような触媒としては、米国特許第４５１００９４号、同第４５３０８７９号、同第６４５１８６９号明細書、欧州特許第３９８７０１号明細書等で報告されている化合物を使用することができ、（η４−ジオレフィン）ジアリール白金、（η５−シクロペンタジエニル）トリアルキル白金、（β−ジケトネート）白金、（β−ケトエステル）白金から選ばれる少なくとも１種の化合物を用いることが好ましい。 In addition, as shown in (III), the addition reaction catalyst itself absorbs ultraviolet rays and exhibits addition reaction activity. As such a catalyst, compounds reported in U.S. Pat. Nos. 4510094, 4530879, 6451869, EP 398701, and the like can be used. It is preferable to use at least one compound selected from olefin) diarylplatinum, (η5-cyclopentadienyl) trialkylplatinum, (β-diketonate) platinum, and (β-ketoester) platinum.
η４で配位するジオレフィンの例としては、ＣＯＤ（シクロオクタジエン）、ＣＯＴ（シクロオクタテトラエン）、ＮＢＤ（ノルボルナジエン）が挙げられるが、これらに限定されるものではない。（η４−ジオレフィン）ジアリール白金の具体例を以下に列挙する。 Examples of the diolefin coordinated by η4 include, but are not limited to, COD (cyclooctadiene), COT (cyclooctatetraene), and NBD (norbornadiene). Specific examples of (η4-diolefin) diarylplatinum are listed below.
（η４−１，５−ＣＯＤ）ジフェニル白金、
（η４−１，３，５，７−ＣＯＴ）ジフェニル白金、
（η４−２，５−ＮＢＤ）ジフェニル白金、
（η４−１，５−ＣＯＤ）ビス（４−メチルフェニル）白金、
（η４−１，５−ＣＯＤ）ビス（２−メチルフェニル）白金、
（η４−１，５−ＣＯＤ）ビス（２−メトキシフェニル）白金、
（η４−１，５−ＣＯＤ）ビス（３−メトキシフェニル）白金、
（η４−１，５−ＣＯＤ）ビス（４−メトキシフェニル）白金、
（η４−１，５−ＣＯＤ）ビス（４−フェノキシフェニル）白金、
（η４−１，５−ＣＯＤ）ビス（４−メチルチオフェニル）白金、
（η４−１，５−ＣＯＤ）ビス（３−クロロフェニル）白金、
（η４−１，５−ＣＯＤ）ビス（４−フルオロフェニル）白金、
（η４−１，５−ＣＯＤ）ビス（４−ブロモフェニル）白金、
（η４−１，５−ＣＯＤ）ビス（２−トリフルオロメチルフェニル）白金、
（η４−１，５−ＣＯＤ）ビス（３−トリフルオロメチルフェニル）白金、
（η４−１，５−ＣＯＤ）ビス（４−トリフルオロメチルフェニル）白金、
（η４−１，５−ＣＯＤ）ビス（２，４，６−トリフルオロフェニル）白金、
（η４−１，５−ＣＯＤ）ビス（ペンタフルオロフェニル）白金、
（η４−１，５−ＣＯＤ）ビス（４−ジメチルアミノフェニル）白金、
（η４−１，５−ＣＯＤ）ビス（４−アセチルフェニル）白金、
（η４−１，５−ＣＯＤ）ビス（４−トリメチルシロキシフェニル）白金、
（η４−１，５−ＣＯＤ）ビス（４−トリメチルシリルフェニル）白金、
（η４−１，５−ＣＯＤ）ビス（１−ナフチル）白金、
（η４−１，５−ＣＯＤ）ビス（キサンテン−１−フェニル）白金、
（η４−１，３−シクロヘキサジエン）ジフェニル白金、
（η４−２，４−ヘキサジエン）ジフェニル白金、
（η４−２，５−ヘプタジエン）ジフェニル白金
(Η4-1,5-COD) diphenyl platinum,
(Η4-1,3,5,7-COT) diphenylplatinum,
(Η4-2,5-NBD) diphenylplatinum,
(Η4-1,5-COD) bis (4-methylphenyl) platinum,
(Η4-1,5-COD) bis (2-methylphenyl) platinum,
(Η4-1,5-COD) bis (2-methoxyphenyl) platinum,
(Η4-1,5-COD) bis (3-methoxyphenyl) platinum,
(Η4-1,5-COD) bis (4-methoxyphenyl) platinum,
(Η4-1,5-COD) bis (4-phenoxyphenyl) platinum,
(Η4-1,5-COD) bis (4-methylthiophenyl) platinum,
(Η4-1,5-COD) bis (3-chlorophenyl) platinum,
(Η4-1,5-COD) bis (4-fluorophenyl) platinum,
(Η4-1,5-COD) bis (4-bromophenyl) platinum,
(Η4-1,5-COD) bis (2-trifluoromethylphenyl) platinum,
(Η4-1,5-COD) bis (3-trifluoromethylphenyl) platinum,
(Η4-1,5-COD) bis (4-trifluoromethylphenyl) platinum,
(Η4-1,5-COD) bis (2,4,6-trifluorophenyl) platinum,
(Η4-1,5-COD) bis (pentafluorophenyl) platinum,
(Η4-1,5-COD) bis (4-dimethylaminophenyl) platinum,
(Η4-1,5-COD) bis (4-acetylphenyl) platinum,
(Η4-1,5-COD) bis (4-trimethylsiloxyphenyl) platinum,
(Η4-1,5-COD) bis (4-trimethylsilylphenyl) platinum,
(Η4-1,5-COD) bis (1-naphthyl) platinum,
(Η4-1,5-COD) bis (xanthene-1-phenyl) platinum,
(Η4-1,3-cyclohexadiene) diphenylplatinum,
(Η4-2,4-hexadiene) diphenylplatinum,
(Η4-2,5-heptadiene) diphenylplatinum
（η５−非置換又は置換シクロペンタジエニル）トリアルキル白金の具体例を以下に示す。η５は省略、Ｃｐはシクロペンタジエニル基、メチル−Ｃｐはメチル置換を表す。 Specific examples of (η5-unsubstituted or substituted cyclopentadienyl) trialkylplatinum are shown below. η5 is omitted, Cp represents a cyclopentadienyl group, and methyl-Cp represents methyl substitution.
（Ｃｐ）トリメチル白金、
（Ｃｐ）エチルジメチル白金、
（Ｃｐ）ジエチルメチル白金、
（Ｃｐ）トリエチル白金、
（Ｃｐ）トリイソプロピル白金、
（Ｃｐ）トリアリル白金、
（Ｃｐ）トリヘキシル白金、
（Ｃｐ）トリシクロペンチル白金、
（Ｃｐ）トリシクロヘキシル白金、
（Ｃｐ）ジメチルベンジル白金、
（メチル−Ｃｐ）トリメチル白金、
（クロロ−Ｃｐ）トリメチル白金、
（フルオロ−Ｃｐ）トリメチル白金、
（トリメチルシリル−Ｃｐ）トリメチル白金、
（ジメチルフェニルシリル−Ｃｐ）トリメチル白金、
［１，３−ビス（トリメチルシリル）−Ｃｐ］トリメチル白金、
１，３−ビス［（Ｃｐ）トリメチル白金］テトラメチルジシロキサン、
（メトキシ−Ｃｐ）トリメチル白金、
（メトキシカルボニル−Ｃｐ）トリメチル白金、
（１，３−ジメチル−Ｃｐ）トリメチル白金、
（１，２，３，４，５−ペンタクロロ−Ｃｐ）トリメチル白金、
（フェニル−Ｃｐ）トリメチル白金、
（４−メチルフェニル−Ｃｐ）トリメチル白金、
（Ｃｐ）アセチルジメチル白金、
（Ｃｐ）アクリロイルジメチル白金、
（Ｃｐ）ドデカノイルジメチル白金、
（Ｃｐ）トリメチル白金を末端に有するポリシロキサン、
［１’−ナフチル−Ｃｐ］トリメチル白金、
［２’−ナフチル−Ｃｐ］トリメチル白金、
［１−メチル−３−（１’−ナフチル）Ｃｐ］トリメチル白金、
［１−メチル−３−（２’−ナフチル）Ｃｐ］トリメチル白金、
［（４’−ビフェニル）Ｃｐ］トリメチル白金、
［（９’−フェナントリル）Ｃｐ］トリメチル白金、
［１−メチル−３−（９’−フェナントリル）Ｃｐ］トリメチル白金
(Cp) trimethylplatinum,
(Cp) ethyldimethylplatinum,
(Cp) diethylmethylplatinum,
(Cp) triethyl platinum,
(Cp) triisopropyl platinum,
(Cp) triallyl platinum,
(Cp) trihexyl platinum,
(Cp) tricyclopentyl platinum,
(Cp) tricyclohexyl platinum,
(Cp) dimethylbenzyl platinum,
(Methyl-Cp) trimethylplatinum,
(Chloro-Cp) trimethylplatinum,
(Fluoro-Cp) trimethylplatinum,
(Trimethylsilyl-Cp) trimethylplatinum,
(Dimethylphenylsilyl-Cp) trimethylplatinum,
[1,3-bis (trimethylsilyl) -Cp] trimethylplatinum,
1,3-bis [(Cp) trimethylplatinum] tetramethyldisiloxane,
(Methoxy-Cp) trimethylplatinum,
(Methoxycarbonyl-Cp) trimethylplatinum,
(1,3-dimethyl-Cp) trimethylplatinum,
(1,2,3,4,5-pentachloro-Cp) trimethylplatinum,
(Phenyl-Cp) trimethylplatinum,
(4-methylphenyl-Cp) trimethylplatinum,
(Cp) acetyldimethylplatinum,
(Cp) acryloyldimethylplatinum,
(Cp) dodecanoyldimethylplatinum,
(Cp) trisiloxane having a terminal polymethylplatinum,
[1′-naphthyl-Cp] trimethylplatinum,
[2′-naphthyl-Cp] trimethylplatinum,
[1-methyl-3- (1′-naphthyl) Cp] trimethylplatinum,
[1-methyl-3- (2′-naphthyl) Cp] trimethylplatinum,
[(4′-biphenyl) Cp] trimethylplatinum,
[(9′-phenanthryl) Cp] trimethylplatinum,
[1-Methyl-3- (9′-phenanthryl) Cp] trimethylplatinum
（β−ジケトネート）、（β−ケトエステル）白金系の配位子となりうる、β−ジケトン、β−ケトエステル類の具体例としては、アセチルアセトン、２，４−ヘキサン−ジオン、２，４−ヘプタン−ジオン、３，５−ヘプタン−ジオン、２，４−オクタン−ジオン、２，４−ノナン−ジオン、５−メチル−ヘキサン−ジオン、２，２，６，６−テトラメチル−３，５−ヘプタン−ジオン、アセト酢酸メチル、アセト酢酸エチル、アセト酢酸ｎ−プロピル、アセト酢酸ｉ−プロピル、アセト酢酸ｎ−ブチル、アセト酢酸ｉ−ブチル、アセト酢酸ｔ−ブチル、アセト酢酸ｓｅｃ−ブチルなどが挙げられる。これらのうち、特にアセチルアセトンが好ましい。 Specific examples of (β-diketonate), (β-ketoester) β-diketone and β-ketoester which can be a platinum-based ligand include acetylacetone, 2,4-hexane-dione, 2,4-heptane- Dione, 3,5-heptane-dione, 2,4-octane-dione, 2,4-nonane-dione, 5-methyl-hexane-dione, 2,2,6,6-tetramethyl-3,5-heptane -Dione, methyl acetoacetate, ethyl acetoacetate, n-propyl acetoacetate, i-propyl acetoacetate, n-butyl acetoacetate, i-butyl acetoacetate, t-butyl acetoacetate, sec-butyl acetoacetate, etc. . Of these, acetylacetone is particularly preferred.
即ち、下記構造式（４）で示されるビス（アセチルアセトナート）白金が好ましい。
上記付加反応触媒（ＩＩＩ）の配合量は触媒量とすることができるが、通常、白金族金属として（Ａ）及び（Ｂ）成分の合計質量に対して１〜２，０００ｐｐｍ、特に２〜１，０００ｐｐｍ程度配合することが好ましい。また、光感応性を更に高めるために、好ましくは（Ｉ）に記載した光増感剤（Ｃ−２）を添加してもよい。この際の光増感剤の添加量は、（Ａ）成分１００質量部に対し、０．１〜１０質量部が好ましく、より好ましくは０．１〜２質量部である。 The addition amount of the addition reaction catalyst (III) can be a catalytic amount, but is usually 1 to 2,000 ppm, particularly 2 to 1 with respect to the total mass of the components (A) and (B) as a platinum group metal. About 1,000 ppm is preferable. Moreover, in order to further improve photosensitivity, you may add the photosensitizer (C-2) described in (I) preferably. 0.1-10 mass parts is preferable with respect to 100 mass parts of (A) component, and, as for the addition amount of the photosensitizer in this case, More preferably, it is 0.1-2 mass parts.
本発明の組成物には、上記（Ａ）〜（Ｃ）成分に加え、任意成分として硬化性、ポットライフを与えるために付加反応制御剤、硬度・粘度を調節するために、例えば脂肪族不飽和結合を含有しないオルガノポリシロキサン、特に非反応性オルガノポリシロキサン、ケイ素原子数が２〜１０個程度の直鎖状又は環状のアルケニル基を含有しない低分子量オルガノポリシロキサンなどを本発明の効果を損なわない範囲で添加してもよい。 In addition to the above components (A) to (C), the composition of the present invention includes an addition reaction control agent for imparting curability and pot life as optional components, The effects of the present invention include organopolysiloxanes that do not contain saturated bonds, especially non-reactive organopolysiloxanes, and low molecular weight organopolysiloxanes that do not contain a linear or cyclic alkenyl group having about 2 to 10 silicon atoms. You may add in the range which does not impair.
更に、透明性に影響を与えない範囲で、強度を向上させるためにヒュームドシリカ等の無機質充填剤を配合してもよいし、必要に応じて波長調整剤、染料、顔料、難燃剤、耐熱剤、耐酸化劣化剤などを配合してもよい。 In addition, inorganic fillers such as fumed silica may be blended to improve the strength within a range that does not affect the transparency, and wavelength adjusters, dyes, pigments, flame retardants, heat resistance as necessary. You may mix | blend an agent, an oxidation-resistant deterioration agent, etc.
本発明の組成物の粘度は、スピンコート法にて均一な膜を形成するというスピンコート塗工性の観点から、組成物の粘度は５〜３０，０００ｍＰａ・ｓが好ましく、より好ましくは１０〜２０，０００ｍＰａ・ｓ、更に好ましくは５０〜１５，０００ｍＰａ・ｓである。 The viscosity of the composition of the present invention is preferably from 5 to 30,000 mPa · s, more preferably from 10 to 30,000 mPa · s, from the viewpoint of spin coat coatability in which a uniform film is formed by spin coating. It is 20,000 mPa · s, more preferably 50 to 15,000 mPa · s.
次に、これら硬化性樹脂組成物から形成される光透過性保護膜について述べると、本発明においては、基板に順次積層された反射層、記録層の上に、上記本発明の組成物を塗工後、硬化することにより形成される光透過性透明保護層を有する光記録媒体とすることが好適である。 Next, the light-transmitting protective film formed from these curable resin compositions will be described. In the present invention, the composition of the present invention is applied on the reflective layer and the recording layer sequentially laminated on the substrate. An optical recording medium having a light-transmitting transparent protective layer formed by curing after the process is preferable.
ここで、支持基板は、光記録材料として使用されている既存の透明有機樹脂或いは無機材料が使用できる。例えばポリカーボネート、ポリアクリレート、ポリメタクリレート、ポリスチレン、ポリエステル、ポリオレフィン、エポキシ樹脂等のプラスチック、ガラスなどが適する。 Here, an existing transparent organic resin or inorganic material used as an optical recording material can be used for the support substrate. For example, polycarbonate, polyacrylate, polymethacrylate, polystyrene, polyester, polyolefin, plastics such as epoxy resin, and glass are suitable.
支持体形状は、既存の形状、具体的には厚みが０．５〜１．５ｍｍ程度、直径８０〜１２０ｍｍ程度の円盤状、カード状等、特に制限なく使用できる。支持体上には、すでに公知の反射層、記録層などが積層される。また、反射層、記録層の形成方法は、真空蒸着法、スパッタリング、イオンプレーティング、有機溶液としてスピンコート法などの公知の方法で形成することができる。 The shape of the support can be used without particular limitation, such as an existing shape, specifically a disc shape or a card shape having a thickness of about 0.5 to 1.5 mm and a diameter of about 80 to 120 mm. Already known reflection layers, recording layers, and the like are laminated on the support. The reflective layer and the recording layer can be formed by a known method such as vacuum deposition, sputtering, ion plating, or spin coating as an organic solution.
本発明の組成物は、記録層の上に特定の膜厚で形成される光透過性保護膜を形成するのに適する。最適膜厚は、膜の屈折率、積層構造などによって異なるが、好ましくは３００μｍ以下、より好ましくは５０〜３００μｍ、更に好ましくは７０〜２００μｍ程度である。また、この膜は、厚さのバラツキが小さいことが好ましく、特に厚みの誤差が±５％以下であることが好ましい。 The composition of the present invention is suitable for forming a light-transmitting protective film formed with a specific thickness on the recording layer. The optimum film thickness varies depending on the refractive index of the film, the laminated structure, etc., but is preferably 300 μm or less, more preferably 50 to 300 μm, and still more preferably about 70 to 200 μm. Further, this film preferably has a small thickness variation, and in particular, the thickness error is preferably ± 5% or less.
なお、光透過性保護膜の形成に用いる硬化装置は公知の加熱乾燥炉、例えば赤外線、熱風乾燥炉を用いることができる。硬化条件は特に制限されないが、４０〜１８０℃、０．５〜１２０分の条件とすることが好ましい。より好ましい条件としては５０〜１３０℃で０．５〜６０分加熱、更に好ましい条件としては６０〜１００℃で０．５〜３０分程度の加熱が好ましい。 In addition, the hardening apparatus used for formation of a light-transmissive protective film can use a well-known heat drying furnace, for example, infrared rays, a hot-air drying furnace. The curing conditions are not particularly limited, but are preferably 40 to 180 ° C. and 0.5 to 120 minutes. More preferable conditions are heating at 50 to 130 ° C. for 0.5 to 60 minutes, and more preferable conditions are heating at 60 to 100 ° C. for about 0.5 to 30 minutes.
また、紫外光によって活性化する白金族金属系触媒を用いる場合、上記組成物の硬化に要する光照射条件は特に制限されないが、光源としてはキセノンランプ、中圧水銀灯、高圧水銀灯、メタルハライドランプ等が好ましい。照射エネルギー量は、１０〜３，０００ｍＪ／ｃｍ2が好ましく、より好ましくは５０〜１，０００ｍＪ／ｃｍ2である。 In addition, when a platinum group metal catalyst activated by ultraviolet light is used, the light irradiation conditions required for curing the composition are not particularly limited, but as a light source, a xenon lamp, a medium pressure mercury lamp, a high pressure mercury lamp, a metal halide lamp, etc. preferable. Irradiation energy is preferably 10~3,000mJ / cm 2, more preferably 50~1,000mJ / cm 2.
以下、実施例及び比較例を示し、本発明を具体的に説明するが、本発明は下記の実施例に制限されるものではない。なお、下記の例においてＰｈはフェニル基を示し、粘度はＢ型回転粘度計により測定した２５℃における値を示す。 EXAMPLES Hereinafter, although an Example and a comparative example are shown and this invention is demonstrated concretely, this invention is not restrict | limited to the following Example. In the following examples, Ph represents a phenyl group, and the viscosity represents a value at 25 ° C. measured with a B-type rotational viscometer.
［実施例１］
下記平均組成式（５）で示され、２５℃における粘度が２７ｍＰａ・ｓであり、かつビニル価が０．５ｍｏｌ／１００ｇであるオルガノポリシロキサン１００質量部、２５℃における３０％トルエン希釈粘度が５，０００ｍＰａ・ｓであり、かつビニル価が０．０７０ｍｏｌ／１０ｇの末端側鎖ビニル基含有ジメチルポリシロキサン（オルガノポリシロキサン生ゴムの３０％トルエン溶液、シリコーン分６質量部）２０質量部、水素ガス発生量が３５０ｍｌ／ｇで、２５℃における粘度が２０ｍＰａ・ｓのメチルハイドロジェンシロキサン４９質量部（総ＳｉＨ基モル量／総アルケニル基モル量＝１．５）と、制御剤としてのエチニルシクロヘキサノール０．５質量部を均一に混合し、この組成物に白金触媒を白金原子として２０ｐｐｍ添加した。この均一に混合した組成物を脱泡後、スピンコート法にて直径１２ｃｍ、厚み１．２ｍｍの円型ポリカーボネート基板へ塗布した。加熱温度８０℃で１０分加熱硬化を行なったところ、タックのない平坦な透明膜（膜厚１０２μｍ）を得た。
[Example 1]
100 parts by mass of an organopolysiloxane represented by the following average composition formula (5) and having a viscosity at 25 ° C. of 27 mPa · s and a vinyl value of 0.5 mol / 100 g, and a 30% toluene dilution viscosity at 25 ° C. of 5 2,000 mPa · s and a vinyl value of 0.070 mol / 10 g of terminal side chain vinyl group-containing dimethylpolysiloxane (30% toluene solution of organopolysiloxane raw rubber, silicone content 6 parts by mass), hydrogen gas generation 49 parts by mass of methyl hydrogen siloxane having an amount of 350 ml / g and a viscosity of 20 mPa · s at 25 ° C. (total SiH group molar amount / total alkenyl group molar amount = 1.5), and ethynylcyclohexanol 0 as a control agent .5 parts by mass are uniformly mixed, and 20 ppm of platinum catalyst is added to this composition as platinum atoms. It was. The uniformly mixed composition was defoamed and then applied to a circular polycarbonate substrate having a diameter of 12 cm and a thickness of 1.2 mm by spin coating. When heat curing was performed at a heating temperature of 80 ° C. for 10 minutes, a flat transparent film (thickness: 102 μm) having no tack was obtained.
［実施例２］
上記平均組成式（５）で示され、２５℃における粘度が２７ｍＰａ・ｓであり、かつビニル価が０．５ｍｏｌ／１００ｇであるオルガノポリシロキサン１００質量部、２５℃における３０％トルエン希釈粘度が２．０ｍＰａ・ｓであり、かつビニル価が０．０８５ｍｏｌ／１００ｇのＱ単位含有オルガノポリシロキサン（シリコーンレジンの３０％トルエン溶液、シリコーン分１００質量部）３３３質量部（トルエン３０％希釈物としての質量）を混合し、１５０℃で溶出分がなくなるまで減圧下ストリップを行った。この混合物に、水素ガス発生量が３５０ｍｌ／ｇで、２５℃における粘度が２０ｍＰａ・ｓのメチルハイドロジェンシロキサン５６質量部（総ＳｉＨ基モル量／総アルケニル基モル量＝１．５）と、制御剤としてのエチニルシクロヘキサノール０．５質量部を均一に混合し、この組成物に白金触媒を白金原子として２０ｐｐｍ添加し、更に均一に混合した組成物を、脱泡後、スピンコート法にて直径１２ｃｍ、厚み１．２ｍｍの円型ポリカーボネート基板へ塗布した。加熱温度８０℃で１０分加熱硬化を行なったところ、タックのない平坦な透明膜（膜厚９８μｍ）を得た。
[Example 2]
100 parts by mass of an organopolysiloxane represented by the above average composition formula (5) and having a viscosity at 25 ° C. of 27 mPa · s and a vinyl value of 0.5 mol / 100 g, and a 30% toluene dilution viscosity at 25 ° C. of 2 0.03 mol / 100 g of Q unit-containing organopolysiloxane (30% toluene solution of silicone resin, 100 parts by weight of silicone) 333 parts by weight (mass of 30% toluene diluted product) ) And stripped under reduced pressure at 150 ° C. until there was no elution. In this mixture, 56 parts by mass of methyl hydrogen siloxane having a hydrogen gas generation amount of 350 ml / g and a viscosity at 25 ° C. of 20 mPa · s (total SiH group molar amount / total alkenyl group molar amount = 1.5) was controlled. 0.5 parts by mass of ethynylcyclohexanol as an agent was uniformly mixed, 20 ppm of platinum catalyst was added to this composition as platinum atoms, and the uniformly mixed composition was defoamed and then subjected to spin coating. It apply | coated to the circular polycarbonate substrate of 12 cm and thickness 1.2mm. When heat curing was performed at a heating temperature of 80 ° C. for 10 minutes, a flat transparent film (film thickness: 98 μm) having no tack was obtained.
［実施例３］
下記平均組成式（６）で示され、２５℃における粘度が４２０ｍＰａ・ｓであり、かつビニル価が０．２３ｍｏｌ／１００ｇであるオルガノポリシロキサン１００質量部、２５℃における３０％トルエン希釈粘度が５，０００ｍＰａ・ｓであり、かつビニル価が０．０７０ｍｏｌ／１００ｇの末端側鎖ビニル基含有ジメチルポリシロキサン２０質量部、水素ガス発生量が３５０ｍｌ／ｇで、２５℃における粘度が２０ｍＰａ・ｓのメチルハイドロジェンシロキサン２３質量部（総ＳｉＨ基モル量／総アルケニル基モル量＝１．５）と、制御剤としてのエチニルシクロヘキサノール０．５質量部を均一に混合し、この組成物に白金触媒を白金原子として２０ｐｐｍ添加した。この均一に混合した組成物を脱泡後、スピンコート法にて直径１２ｃｍ、厚み１．２ｍｍの円型ポリカーボネート基板へ塗布した。加熱温度８０℃で１０分加熱硬化を行なったところ、タックのない平坦な透明膜（膜厚１１０μｍ）を得た。
[Example 3]
100 parts by mass of an organopolysiloxane represented by the following average composition formula (6), having a viscosity at 25 ° C. of 420 mPa · s and a vinyl value of 0.23 mol / 100 g, and a 30% toluene dilution viscosity at 25 ° C. of 5 20 parts by mass of a terminal side chain vinyl group-containing dimethylpolysiloxane having a vinyl value of 0.070 mol / 100 g, a hydrogen gas generation amount of 350 ml / g, and a viscosity at 25 ° C. of 20 mPa · s. 23 parts by mass of hydrogen siloxane (total SiH group molar amount / total alkenyl group molar amount = 1.5) and 0.5 part by mass of ethynylcyclohexanol as a control agent were uniformly mixed, and a platinum catalyst was added to this composition. 20 ppm was added as platinum atoms. The uniformly mixed composition was defoamed and then applied to a circular polycarbonate substrate having a diameter of 12 cm and a thickness of 1.2 mm by spin coating. When heat curing was performed at a heating temperature of 80 ° C. for 10 minutes, a flat transparent film (thickness 110 μm) without tack was obtained.
［実施例４］
上記平均組成式（５）で示され、２５℃における粘度が２７ｍＰａ・ｓであり、かつビニル価が０．５ｍｏｌ／１００ｇであるオルガノポリシロキサン１００質量部、２５℃における３０％トルエン希釈粘度が５，０００ｍＰａ・ｓであり、かつビニル価が０．０７０ｍｏｌ／１００ｇの末端側鎖ビニル基含有ジメチルポリシロキサン２０質量部、水素ガス発生量が３５０ｍｌ／ｇで、２５℃における粘度が２０ｍＰａ・ｓのメチルハイドロジェンシロキサン４９質量部（総ＳｉＨ基モル量／総アルケニル基モル量＝１．５）、制御剤としてのエチニルシクロヘキサノール０．５質量部を均一に混合した。この組成物に塩化白金酸−ビニルシロキサン錯体を白金原子として２００ｐｐｍ、光増感剤として４−メトキシベンゾフェノンを０．５質量部添加した。この均一に混合した組成物を脱泡後、スピンコート法にて直径１２ｃｍ、厚み１．２ｍｍの円型ポリカーボネート基板へ塗布した。６００ｍＪ／ｃｍ2の紫外線照射にて硬化を行い、タックのない平坦な透明膜（膜厚１０８μｍ）を得た。
[Example 4]
100 parts by mass of an organopolysiloxane represented by the above average composition formula (5) and having a viscosity at 25 ° C. of 27 mPa · s and a vinyl value of 0.5 mol / 100 g, and a 30% toluene diluted viscosity at 25 ° C. of 5 20 parts by mass of a terminal side chain vinyl group-containing dimethylpolysiloxane having a vinyl value of 0.070 mol / 100 g, a hydrogen gas generation amount of 350 ml / g, and a viscosity at 25 ° C. of 20 mPa · s. 49 parts by mass of hydrogen siloxane (total SiH group molar amount / total alkenyl group molar amount = 1.5) and 0.5 part by mass of ethynylcyclohexanol as a control agent were uniformly mixed. To this composition, 200 ppm of chloroplatinic acid-vinylsiloxane complex as platinum atoms and 0.5 parts by mass of 4-methoxybenzophenone as a photosensitizer were added. The uniformly mixed composition was defoamed and then applied to a circular polycarbonate substrate having a diameter of 12 cm and a thickness of 1.2 mm by spin coating. Curing was performed by UV irradiation at 600 mJ / cm 2 to obtain a flat transparent film (film thickness: 108 μm) without tack.
［実施例５］
実施例４における制御剤の代わりに、メチルアゾジカルボキシレートを０．１質量部添加した組成物を用いること以外は、実施例４と同様に実施し、タックのない平坦な透明膜（膜厚１０６μｍ）を得た。
[Example 5]
A flat transparent film having no tack (film thickness) was carried out in the same manner as in Example 4 except that a composition containing 0.1 part by mass of methyl azodicarboxylate was used instead of the control agent in Example 4. 106 μm).
［実施例６］
実施例４における白金触媒の代わりに、（トリメチルシリル−Ｃｐ）トリメチル白金を白金原子として２００ｐｐｍ、光増感剤としてフェナントレインを０．５質量部添加した組成物を用いること以外は、実施例４と同様に実施し、タックのない平坦な透明膜（膜厚１０８μｍ）を得た。
[Example 6]
Example 4 was used except that instead of the platinum catalyst in Example 4, a composition in which (trimethylsilyl-Cp) trimethylplatinum was added at 200 ppm as a platinum atom and 0.5 parts by mass of phenanthrene as a photosensitizer was added. And a flat transparent film (thickness: 108 μm) having no tack was obtained.
［実施例７］
上記平均組成式（６）で示され、２５℃における粘度が４２０ｍＰａ・ｓであり、かつビニル価が０．２３ｍｏｌ／１００ｇであるオルガノポリシロキサン１００質量部、２５℃における３０％トルエン希釈粘度が５，０００ｍＰａ・ｓであり、かつビニル価が０．０７０ｍｏｌ／１００ｇの末端側鎖ビニル基含有ジメチルポリシロキサン２０質量部、水素ガス発生量が３５０ｍｌ／ｇで、２５℃における粘度が２０ｍＰａ・ｓのメチルハイドロジェンシロキサン２３質量部（総ＳｉＨ基モル量／総アルケニル基モル量＝１．５）を均一に混合し、この組成物に（１−メチル−３−（９’−フェナントリル）シクロペンタジエニル）トリメチル白金錯体を白金原子として１５０ｐｐｍ添加し、更に均一に混合した組成物を脱泡後、スピンコート法にて直径１２ｃｍ、厚み１．２ｍｍの円型ポリカーボネート基板へ塗布した。３００ｍＪ／ｃｍ2の紫外線照射にて硬化を行い、タックのない平坦な透明膜（膜厚１１２μｍ）を得た。
[Example 7]
100 parts by mass of an organopolysiloxane represented by the above average composition formula (6), having a viscosity at 25 ° C. of 420 mPa · s and a vinyl value of 0.23 mol / 100 g, and a 30% toluene dilution viscosity at 25 ° C. of 5 20 parts by mass of a terminal side chain vinyl group-containing dimethylpolysiloxane having a vinyl value of 0.070 mol / 100 g, a hydrogen gas generation amount of 350 ml / g, and a viscosity at 25 ° C. of 20 mPa · s. 23 parts by mass of hydrogen siloxane (total SiH group molar amount / total alkenyl group molar amount = 1.5) were uniformly mixed, and (1-methyl-3- (9′-phenanthryl) cyclopentadienyl was added to this composition. ) Add 150ppm of trimethylplatinum complex as platinum atom, defoam the composition that was mixed evenly, then spin coat This was applied to a circular polycarbonate substrate having a diameter of 12 cm and a thickness of 1.2 mm by the method. Curing was performed by UV irradiation at 300 mJ / cm 2 to obtain a flat transparent film (film thickness 112 μm) without tack.
［比較例１］
ＵＶ硬化型のアクリル樹脂材料（東亞合成（株）製、アロニックスＭ−８０６０）を入手し、光開始剤（チバスペシャリティーケミカルズ ダロキュアー１１７３）をアクリル樹脂１００質量部に対して２質量部添加し、コート液とした。実施例と同様の円型ポリカーボネート樹脂にスピンコート法にて塗工後、ＵＶを２００ｍＪ／ｃｍ2照射して硬化を行なったところ、タックのない透明膜（膜厚１０６μｍ）を得た。
[Comparative Example 1]
Obtain UV curable acrylic resin material (Aronix M-8060, manufactured by Toagosei Co., Ltd.), add 2 parts by mass of photoinitiator (Ciba Specialty Chemicals Darocur 1173) to 100 parts by mass of acrylic resin, A coating solution was obtained. When the same circular polycarbonate resin as in the example was applied by spin coating and then cured by irradiating with UV of 200 mJ / cm 2 , a tack-free transparent film (film thickness: 106 μm) was obtained.
［比較例２］
ビスフェノールＡ型エポキシアクリレート（ダイセル・ユーシービー（株）製、Ｅｂｅｃｒｙｌ６００）７０質量部、トリメチロールプロパントリアクリレート３０質量部の混合物１００質量部に対し、光開始剤（ダロキュアー１１７３）を２質量部添加し、コート液とした。実施例１と同様、円型ポリカーボネート樹脂にスピンコート法にて塗工後、ＵＶを２００ｍＪ／ｃｍ2照射して硬化を行い、タックのない透明膜（膜厚９０μｍ）を得た。
[Comparative Example 2]
2 parts by mass of a photoinitiator (Darocur 1173) is added to 100 parts by mass of a mixture of 70 parts by mass of bisphenol A type epoxy acrylate (Ebecryl 600, manufactured by Daicel UCB) and 30 parts by mass of trimethylolpropane triacrylate. A coating solution was obtained. As in Example 1, after applying a circular polycarbonate resin by spin coating, the film was cured by irradiation with UV at 200 mJ / cm 2 to obtain a tack-free transparent film (film thickness 90 μm).
評価結果を以下に示す。
体積収縮率：
液状の比重と硬化後の固体比重から体積収縮率を算出した。
反り：
７０℃／２４時間の加熱促進試験を行なった後の上記透明膜を有する基板の反りを目視にて評価した。
鉛筆硬度：
ＪＩＳ Ｋ５６００−５−４引掻き硬度（鉛筆法）により測定した。なお、鉛筆硬度測定用塗膜は、別途、みがき鋼板にバーコーター（Ｎｏ．４６）塗工し、上記と同条件で硬化して作製した。
マジックはじき性：
市販黒マジックインクの塗膜表面への付着具合を評価した。
○：インクがはじいて筆記不可能
×：はじきなく筆記可能
表面接触角：
塗膜の水に対する表面接触角を接触角測定器（協和界面科学社製、形式ＣＡ−Ｘ１５０）にて測定した。
The evaluation results are shown below.
Volumetric shrinkage:
The volume shrinkage was calculated from the liquid specific gravity and the solid specific gravity after curing.
warp:
The warpage of the substrate having the transparent film after the heating acceleration test at 70 ° C./24 hours was visually evaluated.
Pencil hardness:
It was measured by JIS K5600-5-4 scratch hardness (pencil method). The pencil hardness measurement coating was separately prepared by applying a bar coater (No. 46) to a polished steel plate and curing under the same conditions as described above.
Magic repellency:
The degree of adhesion of commercially available black magic ink to the coating surface was evaluated.
○: Writing is impossible due to ink repelling ×: Writing is possible without repelling Surface contact angle:
The surface contact angle of the coating film with respect to water was measured with a contact angle measuring device (manufactured by Kyowa Interface Science Co., Ltd., model CA-X150).
表１の結果から明らかなように、比重から求めた体積収縮率をみると、実施例に挙げた本発明の組成物は、比較例組成物よりも小さいことがわかる。従って光記録媒体の光透過性保護層として用いた場合、内部歪みが少なく、経時での基板の反りを抑えることができる。また、鉛筆硬度の結果より、実施例の塗膜は適度な硬度を有している。マジックはじき性では、実施例シリコーン膜ではマジックのインクがはじくため、汚れにくい特徴が見られた。更に、表面の水の接触角を測定したところ、実施例の膜では高い値を示し、撥水性を有していることが明らかとなった。これは表面からの吸湿による記録層の腐食、劣化を防止する効果を示す。 As is clear from the results in Table 1, it can be seen that the volume shrinkage obtained from the specific gravity is smaller than the composition of the comparative example. Therefore, when used as a light-transmitting protective layer of an optical recording medium, the internal distortion is small and the warping of the substrate over time can be suppressed. Moreover, the coating film of an Example has moderate hardness from the result of pencil hardness. With regard to the magic repellency, the silicone ink of the example silicone film was repelled, so that it was difficult to stain. Furthermore, when the contact angle of water on the surface was measured, the film of the example showed a high value and was found to have water repellency. This shows the effect of preventing corrosion and deterioration of the recording layer due to moisture absorption from the surface.
Claims (8)
（Ｂ）１分子中にケイ素原子と直接結合した水素原子を少なくとも２個有するオルガノハイドロジェンポリシロキサン １〜４００質量部
（Ｃ）触媒量の白金族金属系触媒
を含有し、光透過性保護膜を形成することを特徴とする光記録媒体用硬化性樹脂組成物。 (A) Organopolysiloxane containing at least two substituted or unsubstituted hydrocarbon groups having an aliphatic unsaturated bond in one molecule 100 parts by mass (B) A hydrogen atom directly bonded to a silicon atom in one molecule A curable resin composition for optical recording media, comprising at least two organohydrogenpolysiloxanes having a catalytic amount of platinum group metal catalyst of 1 to 400 parts by mass (C) and forming a light-transmitting protective film Stuff.
Ｒ4 aＨbＳｉＯ(4-a-b)/2 （２）
（式中、Ｒ4はアルケニル基を除く１価の炭化水素基である。ａ，ｂは０．７≦ａ≦２．１、０．００１≦ｂ≦１．０、かつ０．８≦ａ＋ｂ≦２．６を満たす正数であり、１分子中に少なくとも２個のＳｉＨ結合を有し、かつ２５℃での粘度が１，０００ｍＰａ・ｓ以下である。） The composition for optical recording media according to claim 1 or 2, wherein the organohydrogenpolysiloxane (B) is represented by the following average composition formula (2).
R 4 a H b SiO (4-ab) / 2 (2)
(In the formula, R 4 is a monovalent hydrocarbon group excluding an alkenyl group. A and b are 0.7 ≦ a ≦ 2.1, 0.001 ≦ b ≦ 1.0, and 0.8 ≦ a + b. (It is a positive number satisfying ≦ 2.6, having at least two SiH bonds in one molecule, and having a viscosity at 25 ° C. of 1,000 mPa · s or less.)
（η４−ジオレフィン）ジアリール白金
（η５−シクロペンタジエニル）トリアルキル白金
（β−ジケトネート）白金
（β−ケトエステル）白金 The composition for optical recording media according to claim 4, wherein the platinum group metal catalyst (C) is at least one compound selected from the group of photosensitive compounds listed below.
(Η4-diolefin) diarylplatinum (η5-cyclopentadienyl) trialkylplatinum (β-diketonate) platinum (β-ketoester) platinum
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| JP2009019139A (en) * | 2007-07-12 | 2009-01-29 | Kaneka Corp | Curable composition |
| JP2010242087A (en) * | 2009-04-06 | 2010-10-28 | Wacker Chemie Ag | Self-adhesive silicone composition capable of being addition-crosslinked at room temperature by pt catalyst |
| JP2013199629A (en) * | 2012-02-23 | 2013-10-03 | Kaneka Corp | Curable composition, thin film, and thin film transistor using the same |
| JP2013203794A (en) * | 2012-03-27 | 2013-10-07 | Shin-Etsu Chemical Co Ltd | Organopolysiloxane composition, method for curing organopolysiloxane composition and light-emitting diode |
| JP2013540872A (en) * | 2010-10-29 | 2013-11-07 | ワッカー ケミー アクチエンゲゼルシャフト | Photocrosslinkable highly transparent silicone blend |
| JP2015028179A (en) * | 2014-09-25 | 2015-02-12 | 株式会社カネカ | Photocurable composition, and insulating thin film and thin film transistor prepared using the same |
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| JP2013199629A (en) * | 2012-02-23 | 2013-10-03 | Kaneka Corp | Curable composition, thin film, and thin film transistor using the same |
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