KR20230006153A - UV moisture hybrid curable polysiloxane composition, polysiloxane cured film prepared therefrom, and uses thereof - Google Patents
UV moisture hybrid curable polysiloxane composition, polysiloxane cured film prepared therefrom, and uses thereof Download PDFInfo
- Publication number
- KR20230006153A KR20230006153A KR1020210086995A KR20210086995A KR20230006153A KR 20230006153 A KR20230006153 A KR 20230006153A KR 1020210086995 A KR1020210086995 A KR 1020210086995A KR 20210086995 A KR20210086995 A KR 20210086995A KR 20230006153 A KR20230006153 A KR 20230006153A
- Authority
- KR
- South Korea
- Prior art keywords
- polysiloxane composition
- curable polysiloxane
- hybrid curable
- formula
- curing
- Prior art date
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- -1 polysiloxane Polymers 0.000 title claims abstract description 94
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 94
- 239000000203 mixture Substances 0.000 title claims abstract description 81
- 229920006294 polydialkylsiloxane Polymers 0.000 claims abstract description 42
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 12
- 238000001723 curing Methods 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 27
- 238000004519 manufacturing process Methods 0.000 claims description 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 19
- 239000000758 substrate Substances 0.000 claims description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 238000013008 moisture curing Methods 0.000 claims description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 8
- 229910021485 fumed silica Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 238000000016 photochemical curing Methods 0.000 claims description 8
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 6
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 244000028419 Styrax benzoin Species 0.000 claims description 4
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 4
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 4
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 4
- 229960002130 benzoin Drugs 0.000 claims description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 4
- 239000012965 benzophenone Substances 0.000 claims description 4
- 235000019382 gum benzoic Nutrition 0.000 claims description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052753 mercury Inorganic materials 0.000 claims description 4
- 150000002816 nickel compounds Chemical class 0.000 claims description 4
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 4
- 150000003752 zinc compounds Chemical class 0.000 claims description 4
- 150000003754 zirconium Chemical class 0.000 claims description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 150000002923 oximes Chemical class 0.000 claims description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- 150000003606 tin compounds Chemical class 0.000 claims description 3
- 150000003608 titanium Chemical class 0.000 claims description 3
- 238000004904 shortening Methods 0.000 abstract description 3
- 239000010408 film Substances 0.000 description 48
- 239000004205 dimethyl polysiloxane Substances 0.000 description 22
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 22
- 230000000704 physical effect Effects 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000000034 method Methods 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 8
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 6
- 239000010936 titanium Substances 0.000 description 6
- 229910052719 titanium Inorganic materials 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000011256 inorganic filler Substances 0.000 description 5
- 229910003475 inorganic filler Inorganic materials 0.000 description 5
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 5
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 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
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 229940093858 ethyl acetoacetate Drugs 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- RLUFBDIRFJGKLY-UHFFFAOYSA-N (2,3-dichlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1Cl RLUFBDIRFJGKLY-UHFFFAOYSA-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
- XKSUVRWJZCEYQQ-UHFFFAOYSA-N 1,1-dimethoxyethylbenzene Chemical compound COC(C)(OC)C1=CC=CC=C1 XKSUVRWJZCEYQQ-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
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- GIMQKKFOOYOQGB-UHFFFAOYSA-N 2,2-diethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)(OCC)C(=O)C1=CC=CC=C1 GIMQKKFOOYOQGB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 description 1
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 description 1
- IEEJNUOJUZGHHJ-UHFFFAOYSA-L 2-acetyl-3-oxobutanoate;nickel(2+) Chemical compound [Ni+2].CC(=O)C(C(C)=O)C([O-])=O.CC(=O)C(C(C)=O)C([O-])=O IEEJNUOJUZGHHJ-UHFFFAOYSA-L 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
- 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
- YJQMXVDKXSQCDI-UHFFFAOYSA-N 2-ethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3SC2=C1 YJQMXVDKXSQCDI-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
- 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
- MYISVPVWAQRUTL-UHFFFAOYSA-N 2-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=C1 MYISVPVWAQRUTL-UHFFFAOYSA-N 0.000 description 1
- YTPSFXZMJKMUJE-UHFFFAOYSA-N 2-tert-butylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)(C)C)=CC=C3C(=O)C2=C1 YTPSFXZMJKMUJE-UHFFFAOYSA-N 0.000 description 1
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- YDIYEOMDOWUDTJ-UHFFFAOYSA-N 4-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=C(C(O)=O)C=C1 YDIYEOMDOWUDTJ-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- CQQXCSFSYHAZOO-UHFFFAOYSA-L [acetyloxy(dioctyl)stannyl] acetate Chemical compound CCCCCCCC[Sn](OC(C)=O)(OC(C)=O)CCCCCCCC CQQXCSFSYHAZOO-UHFFFAOYSA-L 0.000 description 1
- GPDWNEFHGANACG-UHFFFAOYSA-L [dibutyl(2-ethylhexanoyloxy)stannyl] 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)O[Sn](CCCC)(CCCC)OC(=O)C(CC)CCCC GPDWNEFHGANACG-UHFFFAOYSA-L 0.000 description 1
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- JPUHCPXFQIXLMW-UHFFFAOYSA-N aluminium triethoxide Chemical compound CCO[Al](OCC)OCC JPUHCPXFQIXLMW-UHFFFAOYSA-N 0.000 description 1
- MQPPCKJJFDNPHJ-UHFFFAOYSA-K aluminum;3-oxohexanoate Chemical compound [Al+3].CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O MQPPCKJJFDNPHJ-UHFFFAOYSA-K 0.000 description 1
- BHGPTGSAHKMFSZ-UHFFFAOYSA-M aluminum;octadecanoate;oxygen(2-) Chemical compound [O-2].[Al+3].CCCCCCCCCCCCCCCCCC([O-])=O BHGPTGSAHKMFSZ-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
- QDVNNDYBCWZVTI-UHFFFAOYSA-N bis[4-(ethylamino)phenyl]methanone Chemical compound C1=CC(NCC)=CC=C1C(=O)C1=CC=C(NCC)C=C1 QDVNNDYBCWZVTI-UHFFFAOYSA-N 0.000 description 1
- RDASHQZXQNLNMG-UHFFFAOYSA-N butan-2-olate;di(propan-2-yloxy)alumanylium Chemical compound CCC(C)O[Al](OC(C)C)OC(C)C RDASHQZXQNLNMG-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- CZWLNMOIEMTDJY-UHFFFAOYSA-N hexyl(trimethoxy)silane Chemical compound CCCCCC[Si](OC)(OC)OC CZWLNMOIEMTDJY-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- RJMRIDVWCWSWFR-UHFFFAOYSA-N methyl(tripropoxy)silane Chemical compound CCCO[Si](C)(OCCC)OCCC RJMRIDVWCWSWFR-UHFFFAOYSA-N 0.000 description 1
- HLXDKGBELJJMHR-UHFFFAOYSA-N methyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](C)(OC(C)C)OC(C)C HLXDKGBELJJMHR-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- MNSHGRXIICSKRQ-UHFFFAOYSA-L nickel(2+);3-oxobutanoate Chemical compound [Ni+2].CC(=O)CC([O-])=O.CC(=O)CC([O-])=O MNSHGRXIICSKRQ-UHFFFAOYSA-L 0.000 description 1
- SLYCYWCVSGPDFR-UHFFFAOYSA-N octadecyltrimethoxysilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OC)(OC)OC SLYCYWCVSGPDFR-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- ZMHZSHHZIKJFIR-UHFFFAOYSA-N octyltin Chemical compound CCCCCCCC[Sn] ZMHZSHHZIKJFIR-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- PRCNQQRRDGMPKS-UHFFFAOYSA-N pentane-2,4-dione;zinc Chemical compound [Zn].CC(=O)CC(C)=O.CC(=O)CC(C)=O PRCNQQRRDGMPKS-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- VPLNCHFJAOKWBT-UHFFFAOYSA-N phenyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)C1=CC=CC=C1 VPLNCHFJAOKWBT-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
- 229940095070 tetrapropyl orthosilicate Drugs 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 description 1
- GYZQBXUDWTVJDF-UHFFFAOYSA-N tributoxy(methyl)silane Chemical compound CCCCO[Si](C)(OCCCC)OCCCC GYZQBXUDWTVJDF-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- FZMJEGJVKFTGMU-UHFFFAOYSA-N triethoxy(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC FZMJEGJVKFTGMU-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- 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
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- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
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- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
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- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
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- 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
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- 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
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Abstract
Description
본 발명은 자외선 수분 하이브리드 경화형 폴리실록산 조성물, 이로부터 제조된 폴리실록산 경화막 및 이의 용도에 관한 것이다.The present invention relates to an ultraviolet moisture hybrid curable polysiloxane composition, a polysiloxane cured film prepared therefrom, and uses thereof.
상온에서 공기 중의 수분과 반응하여 경화막을 형성하는 상온수분경화형 조성물은 경화시키는데 가열이 필요하지 않기 때문에, 전기/전자 장치의 밀봉제, 접착제 또는 코팅제로서 사용된다. 특히, 수분경화형 실리콘계 조성물로 제조된 경화막은 넓은 범위의 온도 및 습도 조건에서 안정하고, 신축성, 내충격성 및 절연강도 등의 물리적 물성이 우수하여 널리 사용되고 있다.A room temperature moisture-curable composition that forms a cured film by reacting with moisture in the air at room temperature does not require heating to cure, so it is used as a sealant, adhesive, or coating agent for electrical/electronic devices. In particular, a cured film made of a moisture-curable silicone-based composition is stable in a wide range of temperature and humidity conditions, and is widely used because of its excellent physical properties such as elasticity, impact resistance, and dielectric strength.
하지만, 종래의 수분경화형 실리콘계 조성물은 경화 속도가 느려 생산성이 낮으며, 대량 생산에 적합하지 않은 문제가 있다. 또한, 기판과의 접착력을 높이기 위해서는 경화막의 경도가 낮아지고 표면에 끈적임이 있는 경향이 있으며, 이에 따라 경화막에 손상이 발생하거나 쉽게 벗겨지는 문제가 존재한다.However, the conventional moisture-curable silicone-based composition has a slow curing rate, low productivity, and is not suitable for mass production. In addition, in order to increase adhesion with the substrate, the hardness of the cured film is lowered and the surface tends to be sticky, and thus, there is a problem that the cured film is damaged or easily peeled off.
즉. 기존 실리콘계 경화막의 우수한 물리적 물성을 유지하면서도 향상된 경화속도를 가지며, 우수한 기판과의 접착력 및 표면 끈적임 개선 효과를 동시에 구현할 수 있는 실리콘계 조성물의 개발이 요구된다.In other words. It is required to develop a silicone-based composition capable of simultaneously improving adhesion to a substrate and improving surface stickiness while maintaining excellent physical properties of a conventional silicone-based cured film and having an improved curing speed.
본 발명은 상술한 문제점을 해결하기 위해 안출된 것으로, 경화막 제조 시에 경화 시간을 현저하게 단축시킬 수 있는 하이브리드 경화형 폴리실록산 조성물을 제공하는 것이다.The present invention has been made to solve the above problems, to provide a hybrid curable polysiloxane composition capable of significantly shortening the curing time in preparing a cured film.
또한, 본 발명의 목적은 상기 폴리실록산 조성물을 이용하여 우수한 물리적 물성을 구현할 수 있으며, 표면에 끈적임 현상이 개선된 경화막 및 이를 포함하는 전자소자를 제공하는 것이다. In addition, an object of the present invention is to provide a cured film capable of implementing excellent physical properties by using the polysiloxane composition and having improved stickiness on the surface, and an electronic device including the same.
상술된 목적을 위해, 본 발명은 (a)하기 화학식 1로 표시되는 말단기를 가지는 알콕시 말단 폴리디알킬실록산; (b)(메타)아크릴레이트기 및 히드록시기를 포함하는 말단기를 가지는 폴리디알킬실록산; (c)경화촉매; 및 (d)광개시제;를 포함하는, 하이브리드 경화형 폴리실록산 조성물을 제공한다.For the purpose described above, the present invention provides (a) an alkoxy-terminated polydialkylsiloxane having a terminal group represented by the following formula (1); (b) a polydialkylsiloxane having a terminal group including a (meth)acrylate group and a hydroxyl group; (c) a curing catalyst; And (d) a photoinitiator; it provides a hybrid curable polysiloxane composition comprising a.
[화학식 1] [Formula 1]
(상기 화학식 1에서,(In Formula 1 above,
R1은 (C1-C10)알킬 또는 (C2-C10)알케닐이고;R 1 is (C1-C10)alkyl or (C2-C10)alkenyl;
R2는 (C1-C10)알킬이고;R 2 is (C1-C10)alkyl;
a는 0 또는 1의 정수이다.)a is an integer of 0 or 1.)
본 발명의 일 실시예에 따른 25℃의 온도에서 브룩필드 점도계로 측정한 상기 (a)알콕시말단 폴리디알킬실록산의 점도는 1,000 내지 80,000 cps이고, (b)폴리디알킬실록산의 점도는 100 내지 30,000cps일 수 있다.According to an embodiment of the present invention, the (a) alkoxy-terminated polydialkylsiloxane has a viscosity of 1,000 to 80,000 cps, and (b) the viscosity of the polydialkylsiloxane is 100 to It may be 30,000 cps.
본 발명의 일 실시예에 따른 상기 (a)알콕시 말단 폴리디알킬실록산은 하기 화학식 2로 표시되는 것일 수 있다.The (a) alkoxy-terminated polydialkylsiloxane according to an embodiment of the present invention may be represented by Formula 2 below.
[화학식 2][Formula 2]
(상기 화학식 2에서,(In Formula 2 above,
R1은 (C1-C6)알킬 또는 (C2-C6)알케닐이고;R 1 is (C1-C6)alkyl or (C2-C6)alkenyl;
R2 내지 R4는 각각 독립적으로 (C1-C6)알킬이고;R 2 to R 4 are each independently (C1-C6)alkyl;
a는 0 또는 1의 정수이고;a is an integer of 0 or 1;
n은 1 내지 2,000의 실수이다.)n is a real number from 1 to 2,000.)
본 발명의 일 실시예에 따른 상기 (b)(메타)아크릴레이트기 및 히드록시기를 포함하는 말단기는 하기 화학식 3으로 표시되는 것일 수 있다.The terminal group including the (b) (meth)acrylate group and the hydroxyl group according to an embodiment of the present invention may be represented by Formula 3 below.
[화학식 3][Formula 3]
(상기 화학식 3에서,(In Formula 3,
R5는 수소 또는 (C1-C6)알킬이다.)R 5 is hydrogen or (C1-C6)alkyl.)
본 발명의 일 실시예에 따른 상기 (b)폴리디알킬실록산은 하기 화학식 4로 표시되는 것일 수 있다.The (b) polydialkylsiloxane according to an embodiment of the present invention may be represented by Formula 4 below.
[화학식 4][Formula 4]
(상기 화학식 4에서,(In Chemical Formula 4,
R5는 수소 또는 (C1-C6)알킬이고;R 5 is hydrogen or (C1-C6)alkyl;
R11 내지 R16는 각각 독립적으로 (C1-C6)알킬이고;R 11 to R 16 are each independently (C1-C6)alkyl;
p는 1 내지 2,000의 실수이다.)p is a real number from 1 to 2,000.)
본 발명의 일 실시예에 따른 상기 하이브리드 경화형 폴리실록산 조성물은 접착 부여제를 더 포함하는 것일 수 있다.The hybrid curable polysiloxane composition according to an embodiment of the present invention may further include an adhesion imparting agent.
본 발명의 일 실시예에 따른 상기 접착 부여제는 아민기, 티올기 및 히드록시기에서 선택되는 하나 또는 둘 이상의 반응기를 가지는 알콕시실란; 디알킬디알콕시실란; 알킬트리알콕시실란; 및 테트라알콕시실란;에서 선택되는 것인 하나 또는 둘 이상일 수 있다.The adhesion imparting agent according to an embodiment of the present invention may include an alkoxysilane having one or two or more reactive groups selected from an amine group, a thiol group, and a hydroxy group; dialkyldialkoxysilane; alkyltrialkoxysilanes; And tetraalkoxysilane; it may be one or two or more selected from.
본 발명의 일 실시예에 따른 상기 하이브리드 경화형 폴리실록산 조성물은 흄드 실리카를 더 포함하는 것일 수 있다.The hybrid curable polysiloxane composition according to an embodiment of the present invention may further include fumed silica.
본 발명의 일 실시예에 따른 상기 (c)경화촉매는 유기주석화합물, 유기아연화합물, 유기니켈화합물, 지르코늄 착체, 알루미늄 착체, 및 티타늄 착체에서 선택되는 하나 또는 둘 이상일 수 있다.The (c) curing catalyst according to an embodiment of the present invention may be one or two or more selected from organic tin compounds, organic zinc compounds, organic nickel compounds, zirconium complexes, aluminum complexes, and titanium complexes.
본 발명의 일 실시예에 따른 상기 (d)광개시제는 아세토페논계 화합물, 벤조페논계 화합물, 트리아진계 화합물, 벤조인계 화합물, 이미다졸계 화합물, 크산톤계 화합물, 포스핀계 화합물 및 옥심계 화합물에서 선택되는 하나 또는 둘 이상일 수 있다.The (d) photoinitiator according to an embodiment of the present invention is selected from acetophenone-based compounds, benzophenone-based compounds, triazine-based compounds, benzoin-based compounds, imidazole-based compounds, xanthone-based compounds, phosphine-based compounds and oxime-based compounds It can be one or more than one.
본 발명의 일 실시예에 따른 상기 하이브리드 경화형 폴리실록산 조성물은 (a)알콕시 말단 폴리디알킬실록산 100중량부에 대하여, (b)폴리디알킬실록산 1 내지 20 중량부, (c)경화촉매 0.05 내지 2 중량부, 및 (d)광개시제 0.05 내지 1 중량부를 포함하는 것일 수 있다.The hybrid curable polysiloxane composition according to an embodiment of the present invention contains (a) 1 to 20 parts by weight of polydialkylsiloxane, (c) 0.05 to 2 parts by weight of a curing catalyst, based on 100 parts by weight of alkoxy-terminated polydialkylsiloxane. It may include 0.05 to 1 part by weight, and (d) a photoinitiator.
본 발명의 일 실시예에 따른 상기 하이브리드 경화형 폴리실록산 조성물은 (a)알콕시 말단 폴리디알킬실록산 100중량부에 대하여, 접착 부여제 0.1 내지 5 중량부를 포함하는 것일 수 있다.The hybrid curable polysiloxane composition according to an embodiment of the present invention may include (a) 0.1 to 5 parts by weight of an adhesion imparting agent based on 100 parts by weight of the alkoxy-terminated polydialkylsiloxane.
본 발명의 일 실시예에 따른 상기 하이브리드 경화형 폴리실록산 조성물은 (a)알콕시 말단 폴리디알킬실록산 100중량부에 대하여, 흄드 실리카 1 내지 20 중량부를 포함하는 것일 수 있다.The hybrid curable polysiloxane composition according to an embodiment of the present invention may include (a) 1 to 20 parts by weight of fumed silica based on 100 parts by weight of the alkoxy-terminated polydialkylsiloxane.
본 발명의 일 실시예에 따른 상기 하이브리드 경화형 폴리실록산 조성물은 무수 상태인 것일 수 있다.The hybrid curable polysiloxane composition according to an embodiment of the present invention may be in an anhydrous state.
또한, 본 발명은 상기 하이브리드 경화형 폴리실록산 조성물을 광경화 및 수분경화하여 얻은, 폴리실록산 경화막을 제공한다.In addition, the present invention provides a polysiloxane cured film obtained by photocuring and moisture curing the hybrid curable polysiloxane composition.
또한, 본 발명은 (A)상기 하이브리드 경화형 폴리실록산 조성물을 상대습도 30 내지 90% 에서 기판에 도포하는 단계; 및 (B)광조사를 통해 광경화 및 수분경화하는 단계;를 포함하는, 폴리실록산 경화막의 제조방법을 제공한다.In addition, the present invention includes (A) applying the hybrid curable polysiloxane composition to a substrate at a relative humidity of 30 to 90%; And (B) photo-curing and moisture-curing through light irradiation; provides a method for producing a polysiloxane cured film comprising a.
본 발명의 일 실시예에 따른 상기 단계 (A)의 도포단계 및 (B)의 경화단계는 10 내지 50℃에서 수행되는 것일 수 있다.According to an embodiment of the present invention, the coating step of step (A) and the curing step of (B) may be performed at 10 to 50 ° C.
본 발명의 일 실시예에 따른 상기 광조사는 고압수은램프를 이용하여 수행되는 것일 수 있다.The light irradiation according to an embodiment of the present invention may be performed using a high-pressure mercury lamp.
또한, 본 발명은 상기 폴리실록산 경화막을 포함하는, 전자 소자를 제공한다.In addition, the present invention provides an electronic device including the cured polysiloxane film.
본 발명에 따른 자외선 수분 하이브리드 경화형 폴리실록산 조성물은 경화막 제조 시에 매우 빠른 경화 속도를 구현할 수 있으며, 우수한 물성 및 기판과의 우수한 접착력을 가지는 경화막을 제공할 수 있다.The UV-moisture hybrid curable polysiloxane composition according to the present invention can implement a very fast curing speed when preparing a cured film, and can provide a cured film having excellent physical properties and excellent adhesion to a substrate.
구체적으로, 본 발명에 따른 하이브리드 경화형 폴리실록산 조성물은 상온에서도 경화 속도가 매우 빠르기 때문에 공정시간의 단축이 가능하고, 원가를 절감할 수 있어 경제성을 향상시킬 수 있으며, 대량생산에 적용이 용이할 수 있다. 또한, 상기 하이브리드 경화형 폴리실록산 조성물은 흐름성 및 젖음성이 우수하여 작업성이 좋으며 균일한 두께의 경화막을 제조할 수 있을 뿐만 아니라, 기판과 경화막간의 접착력을 더욱 우수하게 할 수 있다.Specifically, the hybrid curable polysiloxane composition according to the present invention has a very fast curing speed even at room temperature, so the process time can be shortened, cost can be reduced, economic efficiency can be improved, and it can be easily applied to mass production. . In addition, the hybrid curable polysiloxane composition has excellent flowability and wettability, so it has good workability, can produce a cured film having a uniform thickness, and can further improve adhesion between the substrate and the cured film.
또한, 상기 하이브리드 경화형 폴리실록산 조성물로부터 제조된 경화막은 기판과의 접착력이 우수할 뿐만 아니라, 경화막 표면의 끈적임 현상을 효과적으로 개선할 수 있어 경화막 표면에 손상이 발생하거나 쉽게 벗겨지는 문제를 해결할 수 있다.In addition, the cured film prepared from the hybrid curable polysiloxane composition not only has excellent adhesion to the substrate, but also can effectively improve the stickiness of the cured film surface, thereby solving the problem of damage to the cured film surface or easy peeling. .
즉, 본 발명에 따른 하이브리드 경화형 폴리실록산 조성물은 종래의 수분경화형 실록산계 조성물의 경화 속도 문제를 개선함과 동시에, 이로부터 제조된 경화막의 접착력 및 물리적 물성을 동시에 만족할 수 있다.That is, the hybrid curable polysiloxane composition according to the present invention can improve the curing speed problem of the conventional moisture-curable siloxane-based composition, and simultaneously satisfy the adhesive strength and physical properties of a cured film prepared therefrom.
이하, 본 발명을 좀 더 구체적으로 설명한다. 이 때 사용되는 기술 용어 및 과학 용어에 있어서 다른 정의가 없다면, 이 발명이 속하는 기술 분야에서 통상의 지식을 가진 자가 통상적으로 이해하고 있는 의미를 가지며, 하기의 설명에서 본 발명의 요지를 불필요하게 흐릴 수 있는 공지 기능 및 구성에 대한 설명은 생략한다.Hereinafter, the present invention will be described in more detail. If there is no other definition in the technical terms and scientific terms used at this time, they have meanings commonly understood by those of ordinary skill in the art to which this invention belongs, and will unnecessarily obscure the gist of the present invention in the following description. Descriptions of possible known functions and configurations are omitted.
본 발명을 기술하는 명세서 전반에 걸쳐, 어떤 부분이 어떤 구성요소를 "포함"한다는 것은 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성요소를 더 포함할 수 있는 것을 의미하는 것일 수 있다.Throughout the specification describing the present invention, the phrase "includes" a certain element means that a part may further include other elements, not excluding other elements unless otherwise stated. can
본 명세서에서 특별한 정의가 없는 한, 층, 막, 박막, 영역, 판 등의 부분이 다른 부분 "위에" 또는 "상에" 있다고 할 때, 이는 다른 부분 "바로 위에" 있는 경우뿐만 아니라, 그 중간에 또 다른 부분이 있는 경우도 포함하는 것일 수 있다.Unless otherwise defined herein, when a part such as a layer, film, thin film, region, plate, etc. is said to be "on" or "on" another part, this means not only when it is "directly on" the other part, but also in the middle thereof. It may also include the case where there is another part in .
본 명세서의 용어, "하이브리드 경화"는 광조사에 의한 경화 및 수분에 의한 경화가 모두 가능한 것을 의미할 수 있다.As used herein, the term "hybrid curing" may mean that both curing by light irradiation and curing by moisture are possible.
본 명세서의 용어, "표면경화시간(tack free time)"은 표면이 경화되어 피펫이나 손에 시료가 묻어나지 않을 때까지의 시간을 의미할 수 있다.As used herein, the term "tack free time" may refer to the time until the surface is hardened and the sample does not stick to the pipette or hand.
본 명세서의 용어, "완전경화시간"은 경화막의 중심부까지 완전히 경화 될 때까지의 시간을 의미할 수 있다.As used herein, the term "complete curing time" may mean the time until the center of the cured film is completely cured.
본 명세서의 용어, "(메타)아크릴레이트"는 메타아크릴레이트 또는 아크릴레이트를 동시에 의미할 수 있다.As used herein, the term "(meth)acrylate" may mean methacrylate or acrylate at the same time.
이하, 본 발명에 대해 구체적으로 설명한다.Hereinafter, the present invention will be specifically described.
상온수분경화형 폴리실록산계 경화막은 넓은 범위의 온도 및 습도 조건에서 안정하고, 신축성, 내충격성 및 절연강도 등의 물리적 물성이 우수할 뿐만 아니라, 경화막 제조 시 가열 공정이 필요하지 않기 때문에 널리 사용되어왔다. 하지만, 종래의 수분경화형 실리콘계 조성물은 경화 속도가 느려 생산성이 낮으며 대량 생산에 적합하지 않다. 또한, 기판과의 접착력을 높이기 위해서는 경화막의 경도가 낮아지고 표면에 끈적임이 있는 경향이 있으며, 이에 따라 경화막에 손상이 발생하거나 쉽게 벗겨지는 문제가 존재한다.Room-temperature moisture-curable polysiloxane-based cured films have been widely used because they are stable in a wide range of temperature and humidity conditions, have excellent physical properties such as elasticity, impact resistance, and dielectric strength, and do not require a heating process when producing cured films. . However, the conventional moisture-curable silicone-based composition has a low curing rate and low productivity, and is not suitable for mass production. In addition, in order to increase adhesion with the substrate, the hardness of the cured film is lowered and the surface tends to be sticky, and thus, there is a problem that the cured film is damaged or easily peeled off.
본 발명자들은 상기 과제를 해결하기 위하여 많은 연구를 한 결과, 알콕시 말단 폴리디알킬실록산; (메타)아크릴레이트기 및 히드록시기를 포함하는 말단기를 가지는 폴리디알킬실록산; 경화촉매; 및 광개시제;를 포함하는 조성물을 이용하여 광경화 및 수분경화할 때, 경화속도가 매우 빠르며, 경화 후에 표면 끈적임 현상이 없고, 기판과의 접착력이 더욱 우수할 뿐만 아니라, 우수한 물성을 가지는 경화막을 제공할 수 있음을 발견하였다.As a result of many studies to solve the above problems, the inventors of the present invention, alkoxy-terminated polydialkylsiloxane; polydialkylsiloxane having a terminal group including a (meth)acrylate group and a hydroxyl group; curing catalyst; And a photoinitiator; when photo-curing and moisture-curing using a composition containing, the curing speed is very fast, there is no surface stickiness after curing, adhesion to the substrate is more excellent, and a cured film having excellent physical properties is provided. discovered that it could be done.
즉, 상기와 같은 구성을 가지는 폴리실록산 조성물은 종래의 수분경화형 폴리실록산 조성물에 비하여 우수한 물리적 물성을 유지하면서도 기판과의 우수한 접착력 및 표면 끈적임 개선 효과를 동시에 구현할 수 있으며, 경화속도 또한 촉진시킬 수 있음을 발견하여 본 발명을 완성하였다. That is, it was found that the polysiloxane composition having the above configuration can simultaneously realize excellent adhesion to the substrate and surface stickiness improvement effect while maintaining excellent physical properties compared to conventional water-curable polysiloxane compositions, and also accelerate the curing speed. Thus, the present invention was completed.
이하, 본 발명의 각 구성에 대해 보다 구체적으로 설명한다. 그러나 이는 예시적인 것에 불과하며 본 발명이 예시적으로 설명된 구체적인 실시 형태로 제한되는 것은 아니다.Hereinafter, each configuration of the present invention will be described in more detail. However, this is merely an example and the present invention is not limited to the specific embodiments described as examples.
본 발명의 일 양태에 따른 하이브리드 경화형 폴리실록산 조성물은 (a)하기 화학식 1로 표시되는 말단기를 가지는 알콕시 말단 폴리디알킬실록산; (b)(메타)아크릴레이트기 및 히드록시기를 포함하는 말단기를 가지는 폴리디알킬실록산; (c)경화촉매; 및 (d)광개시제;를 포함하는 것일 수 있다.A hybrid curable polysiloxane composition according to one aspect of the present invention includes (a) an alkoxy-terminated polydialkylsiloxane having a terminal group represented by Formula 1 below; (b) a polydialkylsiloxane having a terminal group including a (meth)acrylate group and a hydroxyl group; (c) a curing catalyst; And (d) a photoinitiator; may be one containing.
[화학식 1][Formula 1]
(상기 화학식 1에서,(In Formula 1 above,
R1은 (C1-C10)알킬 또는 (C2-C10)알케닐이고;R 1 is (C1-C10)alkyl or (C2-C10)alkenyl;
R2는 (C1-C10)알킬이고;R 2 is (C1-C10)alkyl;
a는 0 또는 1의 정수이다.)a is an integer of 0 or 1.)
본 발명의 일 양태에 따른 하이브리드 경화형 폴리실록산 조성물은 상기와 같은 성분을 구성성분으로 포함함에 따라, 구성성분들 간에 경화반응과 같은 화학반응이 유도되어 우수한 내구성을 구현하는 경화막을 제공할 수 있다. 또한, 경화 후에 경화막과 기판 간의 우수한 접착력을 확보함과 동시에, 경화막 표면에 끈적임이 남아있는 현상을 개선할 수 있다. 또한, 경화막 제조 시 표면경화시간(tack free time, TFT) 및 완전경화시간을 현저하게 단축시킬 수 있다.As the hybrid curable polysiloxane composition according to one aspect of the present invention includes the above components as components, a chemical reaction such as a curing reaction is induced between the components to provide a cured film that realizes excellent durability. In addition, it is possible to secure excellent adhesion between the cured film and the substrate after curing, and at the same time, it is possible to improve the phenomenon in which stickiness remains on the surface of the cured film. In addition, it is possible to remarkably shorten the surface curing time (tack free time, TFT) and complete curing time when producing a cured film.
구체적으로, 본 발명의 일 양태에 따른 상기 하이브리드 경화형 폴리실록산 조성물은 (a)알콕시 말단 폴리디알킬실록산과 (b)(메타)아크릴기와 히드록시기를 가지는 폴리디알킬실록산을 함께 사용함에 따라, 실온과 같은 낮은 온도에서도 빠른 경화가 가능할 뿐만 아니라 경화가 완료된 후에 경화막 표면의 끈적임이 남아있는 현상을 효과적으로 개선할 수 있다.Specifically, the hybrid curable polysiloxane composition according to one aspect of the present invention uses (a) an alkoxy-terminated polydialkylsiloxane and (b) a (meth)acrylic group and a hydroxyl group-containing polydialkylsiloxane together, Rapid curing is possible even at a low temperature, and the phenomenon in which stickiness of the cured film surface remains after curing is completed can be effectively improved.
본 발명의 일 양태에 따른 상기 화학식 1의 R1은 바람직하게 (C1-C6)알킬 또는 (C2-C6)알케닐일 수 있으며, 보다 바람직하게는 (C1-C3)알킬 또는 (C2-C3)알케닐일 수 있다. 또한, 상기 R2는 바람직하게 (C1-C6)알킬, 보다 바람직하게는 (C1-C3)알킬일 수 있다.R 1 in Formula 1 according to an aspect of the present invention may preferably be (C1-C6)alkyl or (C2-C6)alkenyl, more preferably (C1-C3)alkyl or (C2-C3)alke could be Neil. In addition, R 2 may be preferably (C1-C6)alkyl, more preferably (C1-C3)alkyl.
본 발명의 일 양태에 따른 상기 (a)알콕시 말단 폴리디알킬실록산의 일예는, 보다 바람직하게, 하기 화학식 2로 표시될 수 있다.An example of the (a) alkoxy-terminated polydialkylsiloxane according to an aspect of the present invention may be more preferably represented by Formula 2 below.
[화학식 2][Formula 2]
(상기 화학식 2에서,(In Formula 2 above,
R1은 (C1-C6)알킬 또는 (C2-C6)알케닐이고;R 1 is (C1-C6)alkyl or (C2-C6)alkenyl;
R2 내지 R4는 각각 독립적으로 (C1-C6)알킬이고;R 2 to R 4 are each independently (C1-C6)alkyl;
a는 0 또는 1의 정수이고;a is an integer of 0 or 1;
n은 1 내지 2,000의 실수이다.)n is a real number from 1 to 2,000.)
본 발명의 일 양태에 따른 상기 R3 및 R4는 각각 독립적으로 (C1-C3)알킬일 수 있고, 보다 바람직하게는 하기 화학식 2-1로 표시될 수 있다.According to an aspect of the present invention, R 3 and R 4 may each independently be (C1-C3)alkyl, and more preferably represented by Formula 2-1 below.
[화학식 2-1][Formula 2-1]
(상기 화학식 2-1에서,(In Chemical Formula 2-1,
R1, R2, a 및 n의 정의는 상기 화학식 2에서의 정의와 동일하다.)The definitions of R 1 , R 2 , a and n are the same as those in Formula 2 above.)
본 발명의 일 양태에 따른 상기 (a)알콕시 말단 폴리디알킬실록산은, 보다 바람직하게, 하기 화학식 2-2 또는 2-3으로 표시될 수 있다.The (a) alkoxy-terminated polydialkylsiloxane according to one aspect of the present invention may be more preferably represented by Formula 2-2 or 2-3.
[화학식 2-2][Formula 2-2]
[화학식 2-3][Formula 2-3]
(상기 화학식 2-2 및 2-3에 있어서,(In Chemical Formulas 2-2 and 2-3,
R은 (C1-C6)알킬이고;R is (C1-C6)alkyl;
R'은 (C1-C6)알킬 또는 (C2-C6)알케닐이고;R' is (C1-C6)alkyl or (C2-C6)alkenyl;
n 및 m은 각각 독립적으로 1 내지 1,000의 실수이다.)n and m are each independently a real number from 1 to 1,000.)
또한, 본 발명의 일 양태에 따른 상기 (a)알콕시 말단 폴리디알킬실록산은 25℃의 온도에서 브룩필드 점도계로 측정한 점도 값이 1,000 내지 80,000 cps일 수 있고, 좋게는 5,000 내지 30,000 cps일 수 있다. 상기 점도 범위를 만족함에 따라, 작업성을 좋게 할 수 있을 뿐만 아니라, 하이브리드 경화형 폴리실록산 조성물의 젖음성 및 흐름성을 더욱 향상시킬 수 있다. 또한, 기판과의 표면 접촉이 향상될 수 있고, 기판과 경화막간의 접착력을 더욱 우수하게 할 수 있다.In addition, the (a) alkoxy-terminated polydialkylsiloxane according to one aspect of the present invention may have a viscosity value of 1,000 to 80,000 cps, preferably 5,000 to 30,000 cps, as measured by a Brookfield viscometer at a temperature of 25 ° C. there is. When the above viscosity range is satisfied, workability may be improved, and wettability and flowability of the hybrid curable polysiloxane composition may be further improved. In addition, surface contact with the substrate can be improved, and adhesion between the substrate and the cured film can be further improved.
본 발명의 일 양태에 따른 상기 (b)의 (메타)아크릴레이트기 및 히드록시기를 포함하는 말단기는 그 일예로서 하기 화학식 3으로 표시될 수 있다.The terminal group including a (meth)acrylate group and a hydroxyl group of (b) according to an aspect of the present invention may be represented by Formula 3 below as an example thereof.
[화학식 3][Formula 3]
(상기 화학식 3에서,(In Formula 3,
R5는 수소 또는 (C1-C6)알킬이다.)R 5 is hydrogen or (C1-C6)alkyl.)
상기 화학식 3과 같이 히드록시기 및 (메타)아크릴레이트기를 동시에 포함함에 따라, 상기 하이브리드 경화형 폴리실록산 조성물의 표면경화속도를 더욱 우수하게 할 수 있을 뿐만 아니라, 경화 후에 경화막 표면 끈적임 현상을 더욱 효과적으로 개선할 수 있다. 상기 (메타)아크릴레이트기 대신에 비닐기 또는 알릴기를 포함할 경우, 완전히 경화된 후에도 경화막 표면에 끈적임이 남아있을 수 있어서 선호되지 않는다.By including a hydroxyl group and a (meth)acrylate group as shown in Formula 3, the surface curing speed of the hybrid curable polysiloxane composition can be further improved, and the surface stickiness of the cured film after curing can be more effectively improved. there is. When a vinyl group or an allyl group is included instead of the (meth)acrylate group, stickiness may remain on the surface of the cured film even after complete curing, which is not preferred.
본 발명의 일 양태에 따른 상기 (b)폴리디알킬실록산은 그 일예로서, 하기 화학식 4로 표시될 수 있다.As an example, the (b) polydialkylsiloxane according to an aspect of the present invention may be represented by Formula 4 below.
[화학식 4][Formula 4]
(상기 화학식 4 에서,(In Formula 4 above,
R5는 수소 또는 (C1-C6)알킬이고;R 5 is hydrogen or (C1-C6)alkyl;
R11 내지 R25는 각각 독립적으로 (C1-C6)알킬이고;R 11 to R 25 are each independently (C1-C6)alkyl;
p는 1 내지 2,000의 실수이다.)p is a real number from 1 to 2,000.)
본 발명의 일 양태에 따른 상기 R5는 수소 또는 (C1-C3)알킬일 수 있고, 상기 R11 내지 R16은 각각 독립적으로 (C1-C3)알킬일 수 있으며, 상기 p는 10 내지 2,000의 실수일 수 있다.According to an aspect of the present invention, R 5 may be hydrogen or (C1-C3)alkyl, and R 11 to R 16 may each independently be (C1-C3)alkyl, wherein p is 10 to 2,000 Could be a mistake.
보다 바람직하게, 상기 (b)폴리디알킬실록산은 하기 화학식 4-1로 표시될 수 있다.More preferably, the (b) polydialkylsiloxane may be represented by the following Chemical Formula 4-1.
[화학식 4-1][Formula 4-1]
(상기 화학식 4-1에서,(In Chemical Formula 4-1,
R5는 수소 또는 (C1-C3)알킬이고;R 5 is hydrogen or (C1-C3)alkyl;
p는 1 내지 2,000의 실수이다.)p is a real number from 1 to 2,000.)
또한, 본 발명의 일 양태에 따른 상기 (b)폴리디알킬실록산은 25℃의 온도에서 브룩필드 점도계로 측정한 점도 값이 100 내지 30,000cps일 수 있고, 좋게는 500 내지 20,000 cps일 수 있다. 상기 점도 범위를 만족함에 따라, 본 발명의 일 양태에 따른 하이브리드 경화형 폴리실록산 조성물의 젖음성 및 퍼짐성을 더욱 향상시킬 수 있으며, 기판과 경화막간의 접착력을 더욱 우수하게 할 수 있다. 또한, 경화시간도 촉진될 수 있다.In addition, the (b) polydialkylsiloxane according to an aspect of the present invention may have a viscosity value of 100 to 30,000 cps, preferably 500 to 20,000 cps, as measured by a Brookfield viscometer at a temperature of 25 °C. When the above viscosity range is satisfied, wettability and spreadability of the hybrid curable polysiloxane composition according to an aspect of the present invention may be further improved, and adhesion between the substrate and the cured film may be further improved. Also, the curing time can be accelerated.
또한, 상기 (b)폴리디알킬실록산은 (a)알콕시 말단 폴리디알킬실록산 100중량부에 대하여, 본 발명의 목적을 달성하는 한에서는 제한하지 않지만, 예를 들면, 1 내지 20 중량부, 좋게는 5 내지 20 중량부, 더욱 좋게는 5 내지 15 중량부를 포함하는 것일 수 있다. 상술한 중량부의 (b)폴리디알킬실록산을 포함함에 따라, 폴리실록산 조성물의 표면경화속도를 더욱 우수하게 할 수 있으며, 내구성이 탁월한 경화막을 제공할 수 있다.In addition, the (b) polydialkylsiloxane is not limited as long as the object of the present invention is achieved with respect to 100 parts by weight of (a) alkoxy-terminated polydialkylsiloxane, but for example, 1 to 20 parts by weight, preferably It may include 5 to 20 parts by weight, more preferably 5 to 15 parts by weight. By including the above-described weight part (b) polydialkylsiloxane, the surface curing rate of the polysiloxane composition can be further improved, and a cured film with excellent durability can be provided.
본 발명의 일 양태에 따른 상기 (c)경화촉매는 유기주석화합물, 유기아연화합물, 유기니켈화합물, 지르코늄 착체, 알루미늄 착체, 및 티타늄 착체에서 선택되는 하나 또는 둘 이상일 수 있다. 상기 유기주석화합물은, 예를 들어, 디부틸 주석 옥토에이트, 디부틸주석 디라우레이트, 디부틸주석 디(2-에틸헥사노에이트), 디옥틸주석 디라우레이트, 디옥틸주석 디아세테이트, 디옥틸주석 디옥토에이트 등의 유기주석화합물; 옥틸산아연, 아연(Ⅱ) 아세틸아세토네이트 등의 유기아연, 니켈아세틸아세토에이트, 니켈디아세틸아세토에이트 등의 유기니켈화합물; 지르코늄 테트라(아세틸아세토네이트), 지르코늄 테트라부틸레이트 등의 지르코늄 착체; 알루미늄 트리스(아세틸아세토네이트), 알루미늄이소프로필레이트, 모노sec-부톡시알루미늄디이소프로필레이트, 알루미늄 sec-부틸레이트, 알루미늄에틸레이트, 에틸아세토아세테이트알루미늄디이소프로필레이트, 알루미늄트리스(에틸아세토아세테이트), 알킬아세토아세테이트알루미늄디이소프로필레이트, 알루미늄모노아세틸아세토 네이트비스(에틸아세토아세테이트), 알루미늄트리스(아세틸아세토네이트), 알루미늄모노이소프로폭시모노올레옥 시에틸아세토아세테이트, 환상 알루미늄옥사이드이소프로필레이트, 환상 알루미늄옥사이드옥틸레이트, 환상 알루미늄옥사이드스테아레이트 등의 알루미늄 착체; 디이소프로폭시 비스(아세틸아세토네이트)티탄, 디이소프로폭시비스(트리에탄올아미네이트)티탄, 디-n-부톡시비스(트리에탄올 아미네이트)티탄, 디(2-에틸헥실록시)비스(2-에틸-1,3-헥산디올라토)티탄, 이소프로폭시(2-에틸헥산디올 라토)티탄, 테트라아세틸아세토네이트티탄, 히드록시비스(락테이트)티탄 등의 티타늄 착체;에서 선택되는 하나 또는 둘 이상일 수 있으나, 이에 한정되는 것은 아니다.The (c) curing catalyst according to an aspect of the present invention may be one or two or more selected from organic tin compounds, organic zinc compounds, organic nickel compounds, zirconium complexes, aluminum complexes, and titanium complexes. The organotin compound may be, for example, dibutyltin octoate, dibutyltin dilaurate, dibutyltin di(2-ethylhexanoate), dioctyltin dilaurate, dioctyltin diacetate, dibutyltin diacetate, organotin compounds such as octyltin dioctoate; organic zinc compounds such as zinc octylate and zinc (II) acetylacetonate; organic nickel compounds such as nickel acetylacetoate and nickel diacetylacetoate; zirconium complexes such as zirconium tetra(acetylacetonate) and zirconium tetrabutylate; Aluminum tris(acetylacetonate), aluminum isopropylate, monosec-butoxyaluminum diisopropylate, aluminum sec-butylate, aluminum ethylate, ethylacetoacetate, aluminum diisopropylate, aluminum tris(ethylacetoacetate) , Alkyl acetoacetate aluminum diisopropylate, aluminum monoacetylacetonate bis(ethylacetoacetate), aluminum tris(acetylacetonate), aluminum monoisopropoxymonoleoxyethylacetoacetate, cyclic aluminum oxide isopropylate, aluminum complexes such as cyclic aluminum oxide octylate and cyclic aluminum oxide stearate; Diisopropoxybis(acetylacetonate)titanium, diisopropoxybis(triethanolaminate)titanium, di-n-butoxybis(triethanolaminate)titanium, di(2-ethylhexyloxy)bis(2 -Titanium complexes such as ethyl-1,3-hexanediolato)titanium, isopropoxy(2-ethylhexanediolato)titanium, tetraacetylacetonatetitanium, and hydroxybis(lactate)titanium; one selected from or It may be two or more, but is not limited thereto.
또한, 상기 (c)경화촉매는 (a)알콕시 말단 폴리디알킬실록산 100중량부에 대하여, 0.05 내지 2 중량부, 좋게는 0.05 내지 1 중량부, 더욱 좋게는 0.1 내지 1 중량부를 포함하는 것일 수 있다. 상기 중량부의 경화촉매를 포함함에 따라, 조성물의 안정성을 저하시키지 않으면서 수분에 의한 알콕시기의 축합 반응을 더욱 촉진시킬 수 있다.In addition, the (c) curing catalyst may contain 0.05 to 2 parts by weight, preferably 0.05 to 1 part by weight, more preferably 0.1 to 1 part by weight, based on 100 parts by weight of the alkoxy-terminated polydialkylsiloxane (a). there is. As the curing catalyst is included in parts by weight, the condensation reaction of the alkoxy group due to moisture can be further promoted without reducing the stability of the composition.
본 발명의 일 양태에 따른 상기 (d)광개시제는 예를 들어, 벤조페논계 화합물, 트리아진계 화합물, 벤조인계 화합물, 이미다졸계 화합물, 크산톤계 화합물, 포스핀계 화합물 및 옥심계 화합물에서 선택되는 하나 또는 둘 이상일 수 있다. 보다 구체적으로, 벤조인, 벤조인 메틸에테르, 벤조인 에틸에테르, 벤조인 이소프로필에테르, 벤조인 n-부틸에테르, 벤조인 이소부틸에테르, 아세토페논, 디메틸아니노 아세토페논, 2,2- 디메톡시-2-페닐아세토페논, 2,2-디에톡시-2-페닐아세토페논, 2-히드록시-2-메틸-1-페닐프로판-1온, 1-히드록시 시클로헥실페닐케톤, 2-메틸-1-[4-(메틸티오)페닐]-2-몰포리노-프로판-1-온, 4-(2-히드록시에톡시)페닐-2-(히드록시-2-프로필)케톤, 벤조페논, p-페닐벤조페논, 4,4'-디에틸아미노벤조페논, 디클로로벤조페논, 2-메틸안트라퀴논, 2-에틸안트라퀴논, 2-t-부틸안트라퀴논, 2-아미노안트라퀴논, 2-메틸티오잔톤(thioxanthone), 2-에틸티오 잔톤, 2-클로로티오잔톤, 2,4-디메틸티오잔톤, 2,4-디에틸티오잔톤, 벤질디메틸케탈, 아세토페논 디메틸케탈, p-디메틸아미노 안식향산 에스테르, 올리고[2-히드록시-2-메틸-1-[4-(1-메틸비닐)페닐]프로판논] 및 2,4,6-트메틸벤조일-디페닐-포스핀옥시드에서 선택되는 하나 또는 둘 이상일 수 있으나, 이에 한정되는 것은 아니다.The (d) photoinitiator according to one aspect of the present invention is, for example, one selected from benzophenone-based compounds, triazine-based compounds, benzoin-based compounds, imidazole-based compounds, xanthone-based compounds, phosphine-based compounds and oxime-based compounds or two or more. More specifically, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin n-butyl ether, benzoin isobutyl ether, acetophenone, dimethylano acetophenone, 2,2-dimethine Toxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1one, 1-hydroxycyclohexylphenylketone, 2-methyl -1-[4-(methylthio)phenyl]-2-morpholino-propan-1-one, 4-(2-hydroxyethoxy)phenyl-2-(hydroxy-2-propyl)ketone, benzophenone , p-phenylbenzophenone, 4,4'-diethylaminobenzophenone, dichlorobenzophenone, 2-methylanthraquinone, 2-ethylanthraquinone, 2-t-butylanthraquinone, 2-aminoanthraquinone, 2- Methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, benzyldimethylketal, acetophenone dimethylketal, p-dimethylaminobenzoic acid One selected from esters, oligo[2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propanone] and 2,4,6-tmethylbenzoyl-diphenyl-phosphineoxide Or it may be two or more, but is not limited thereto.
또한, 상기 (d)광개시제는 (a)알콕시 말단 폴리디알킬실록산 100중량부에 대하여, 0.05 내지 1 중량부, 좋게는 0.05 내지 0.5 중량부, 더욱 좋게는 0.1 내지 0.5 중량부를 포함하는 것일 수 있다.In addition, the (d) photoinitiator may include 0.05 to 1 part by weight, preferably 0.05 to 0.5 parts by weight, and more preferably 0.1 to 0.5 parts by weight based on 100 parts by weight of the alkoxy-terminated polydialkylsiloxane (a). .
본 발명의 일 양태에 따른 상기 하이브리드 경화형 폴리실록산 조성물은 접착 부여제를 더 포함하는 것일 수 있다. 상기 접착 부여제는 아민기, 티올기 및 히드록시기에서 선택되는 하나 또는 둘 이상의 반응기를 가지는 알콕시실란; 디알킬디알콕시실란; 알킬트리알콕시실란; 테트라알콕시실란; 또는 이들의 조합에서 선택되는 것일 수 있다.The hybrid curable polysiloxane composition according to one aspect of the present invention may further include an adhesion imparting agent. The adhesion imparting agent is an alkoxysilane having one or two or more reactive groups selected from an amine group, a thiol group and a hydroxyl group; dialkyldialkoxysilane; alkyltrialkoxysilanes; tetraalkoxysilane; Or it may be selected from a combination thereof.
상기 접착 부여제는 예를 들어, 3-아미노프로필트리메톡시실란, 3-아미노프로필트리에톡시실란, N-페닐-3-아미노프로필트리메톡시실란, N-2-(아미노에틸)-3-아미노프로필메틸디메톡시실란, N-2-(아미노에틸)-3-아미노프로필트리메톡시실란 및 N-2-(아미노에틸)-8-아미노옥틸트리메톡시실란, (3-머캅토프로필)트리메톡시실란, (3-머캅토프로필)트리에톡시실란, 디메틸디메톡시실란, 디메틸디에톡시실란, 메틸트리메톡시실란, 메틸트리에톡시실란, 메틸트리프로폭시실란, 메틸트리이소프로폭시실란, 메틸트리부톡시실란, 에틸트리메톡시실란, 에틸트리에톡시실란, 헥실트리메톡시실란, 옥타데실트리메톡시실란, 옥타데실트리에톡시실란, 페닐트리메톡시실란, 페닐트리에톡시실란, 페닐트리이소프로폭시실란, 테트라메틸오르쏘실리케이트, 테트라에틸오르쏘실리케이트, 테트라프로필오르쏘실리케이트, 테트라부틸오르쏘실리케이트 및 테트라펜틸으로쏘실리케이트에서 선택되는 하나 또는 둘 이상일 수 있으나, 이에 한정되는 것은 아니다.The adhesion imparting agent is, for example, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, N-2-(aminoethyl)-3 -aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane and N-2-(aminoethyl)-8-aminooctyltrimethoxysilane, (3-mercaptopropyl )trimethoxysilane, (3-mercaptopropyl)triethoxysilane, dimethyldimethoxysilane, dimethyldiethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, methyltripropoxysilane, methyltriisopro Poxysilane, methyltributoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, hexyltrimethoxysilane, octadecyltrimethoxysilane, octadecyltriethoxysilane, phenyltrimethoxysilane, phenyltrie It may be one or two or more selected from toxysilane, phenyltriisopropoxysilane, tetramethylorthosilicate, tetraethylorthosilicate, tetrapropylorthosilicate, tetrabutylorthosilicate, and tetrapentyllossosilicate. It is not limited.
또한, 상기 접착 부여제는 (a)알콕시 말단 폴리디알킬실록산 100중량부에 대하여, 0.01 내지 10 중량부, 좋게는 0.5 내지 5 중량부를 포함하는 것일 수 있다. 상기 중량부의 접착 부여제를 더 포함함에 따라, 하이브리드 경화형 폴리실록산 조성물의 경화시간 단축, 경화막의 내구성 개선 및 표면 끈적임 현상 개선 등의 효과를 더욱 효과적으로 향상시킬 수 있다.In addition, the adhesion imparting agent (a) may include 0.01 to 10 parts by weight, preferably 0.5 to 5 parts by weight based on 100 parts by weight of the alkoxy-terminated polydialkylsiloxane. By further including the adhesion imparting agent by weight, effects such as shortening of curing time of the hybrid curable polysiloxane composition, improvement of durability of cured film, and improvement of surface stickiness can be more effectively improved.
본 발명의 일 양태에 따른 하이브리드 경화형 폴리실록산 조성물은 무기 충전제를 더 포함할 수 있다. 상기 무기 충전제는 이 분야에 사용하는 무기충진제라면 특별히 한정하지 않지만, 예를 들어, 실리카, 탈크, 이산화티탄, 산화알루미늄, 탄산칼슘, 규산알루미늄, 규산마그네슘 및 산화지르코늄 등에서 선택되는 하나 또는 둘 이상일 수 있고, 바람직하게는 실리카일 수 있으나, 이에 제한되는 것은 아니다. 구체적으로, 상기 실리카는 침강 실리카 또는 흄드 실리카를 포함할 수 있고, 흄드 실리카를 사용하는 것이 더욱 바람직할 수 있다.The hybrid curable polysiloxane composition according to one aspect of the present invention may further include an inorganic filler. The inorganic filler is not particularly limited as long as it is an inorganic filler used in this field, but for example, it may be one or two or more selected from silica, talc, titanium dioxide, aluminum oxide, calcium carbonate, aluminum silicate, magnesium silicate, and zirconium oxide. And, preferably, it may be silica, but is not limited thereto. Specifically, the silica may include precipitated silica or fumed silica, and it may be more preferable to use fumed silica.
또한, 상기 무기충진제를 사용하는 경우, 그 함량은 본 발명의 목적을 달성하는 한에서는 특별히 한정하지 않지만, 예를 들면, (a)알콕시 말단 폴리디알킬실록산 100중량부에 대하여, 1 내지 20 중량부를 포함하는 것일 수 있다. 상기 중량부 범위의 무기 충전제를 더 포함함에 따라, 하이브리드 경화형 폴리실록산 조성물의 점도 및 저장안정성을 더욱 용이하게 제어할 수 있으며, 경화 후 형성된 경화막의 기계적 물성을 더욱 우수하게 할 수 있다.In addition, when the inorganic filler is used, its content is not particularly limited as long as it achieves the object of the present invention, but, for example, (a) 1 to 20 parts by weight based on 100 parts by weight of alkoxy-terminated polydialkylsiloxane may include As the inorganic filler is further included in the range of parts by weight, the viscosity and storage stability of the hybrid curable polysiloxane composition can be more easily controlled, and the mechanical properties of the cured film formed after curing can be further improved.
또한, 본 발명은 반응촉진제로서 헥사알킬디실라잔을 더 포함할 수 있다, 상기 반응촉진제는 축합물에서 부반응물인 알코올을 트랩하여 반응하므로, 전체적인 경화 반응을 순방향으로 촉진시키고 물성을 더욱 우수하게 유도하는 것이어서 좋다. 좋게는, 상기 (a)성분의 알콕시기의 당량과 동일하거나 적게 사용하는 것이 바람직하므로 이의 함량을 한정하지 않는다. 좋게는, 상기 (a)알콕시 말단 폴리디알킬실록산 100중량부에 대하여, 0.5 내지 10 중량부를 포함하는 것일 수 있다. 상기 중량부 범위의 반응촉진제를 더 포함함에 따라, 하이브리드 경화형 폴리실록산 조성물의 표면경화시간을 단축하는데 있어서 시너지 효과를 부여할 수 있다.In addition, the present invention may further include hexaalkyldisilazane as a reaction promoter. Since the reaction promoter reacts by trapping alcohol, which is a side reactant in the condensate, promotes the overall curing reaction in the forward direction and improves physical properties. It is good that it induces. Preferably, it is preferable to use the same or less than the equivalent of the alkoxy group of the component (a), so the content thereof is not limited. Preferably, it may include 0.5 to 10 parts by weight based on 100 parts by weight of the (a) alkoxy-terminated polydialkylsiloxane. As the reaction promoter is further included in the range of parts by weight, a synergistic effect can be imparted in reducing the surface curing time of the hybrid curable polysiloxane composition.
본 발명의 일 양태에 따른 상기 하이브리드 경화형 폴리실록산 조성물은 무수 상태일 수 있으며, 이에 따라, 추후 가습조건 하에서 수분에 의한 경화 반응이 용이하게 수행될 수 있다.The hybrid curable polysiloxane composition according to one aspect of the present invention may be in an anhydrous state, and thus, a curing reaction by moisture may be easily performed under a humidified condition later.
또한, 본 발명의 일 양태에 따른 상기 하이브리드 경화형 폴리실록산 조성물은 컨포멀 코팅제(conformal coating agent)로 사용될 수 있으며, 바람직하게는 전자 소자를 위한 컨포멀 코팅제로 사용될 수 있다.In addition, the hybrid curable polysiloxane composition according to one aspect of the present invention may be used as a conformal coating agent, preferably a conformal coating agent for electronic devices.
또한, 본 발명의 일 양태는 상기 하이브리드 경화형 폴리실록산 조성물을 광경화 및 수분경화하여 얻은, 폴리실록산 경화막 및 이를 포함하는 전자 소자를 제공한다. In addition, one aspect of the present invention provides a cured polysiloxane film obtained by photocuring and moisture curing the hybrid curable polysiloxane composition, and an electronic device including the same.
상기 전자 소자는 특별히 제한되지 않지만 전기 회로 또는 전극 등을 포함하는 전자 소자일 수 있으며, 예를 들어, 저항기, 커패시터, 트랜지스터, 다이오드, 증폭기, 릴레이, 변압기, 배터리, 퓨즈, 집적회로, 스위치, LED, 안테나 및오실레이터 등을 포함할 수 있다.The electronic device is not particularly limited, but may be an electronic device including an electric circuit or an electrode, for example, a resistor, a capacitor, a transistor, a diode, an amplifier, a relay, a transformer, a battery, a fuse, an integrated circuit, a switch, and an LED. , an antenna, and an oscillator.
본 발명의 일 양태에 따른 상기 폴리실록산 경화막의 제조방법은 당업자가 인식할 수 있는 범위 내 공지의 방법이라면 모두 가능함은 물론이다.Of course, any method for producing the cured polysiloxane film according to an aspect of the present invention can be any known method within the range recognized by those skilled in the art.
이하, 상기 하이브리드 경화형 폴리실록산 조성물을 이용한 폴리실록산 경화막의 형성 방법에 대해 구체적으로 설명한다.Hereinafter, a method of forming a cured polysiloxane film using the hybrid curable polysiloxane composition will be described in detail.
본 발명의 일 양태에 따른 폴리실록산 경화막은 (A)상기 하이브리드 경화형 폴리실록산 조성물을 상대습도 30 내지 90% 에서 기판에 도포하는 단계; 및 (B)광조사를 통해 광경화 및 수분경화하는 단계;를 포함하는 제조방법으로 제조될 수 있다.A polysiloxane cured film according to an aspect of the present invention comprises the steps of (A) applying the hybrid curable polysiloxane composition to a substrate at a relative humidity of 30 to 90%; And (B) photocuring and moisture curing through light irradiation; it can be prepared by a manufacturing method comprising a.
본 발명의 일 양태에 따른 상기 폴리실록산 경화막의 제조는 10 내지 50℃에서 수행되는 것을 특징으로 할 수 있으며, 좋게는 10 내지 30℃, 더욱 좋게는 20 내지 30℃에서 수행되는 것일 수 있다. 즉, 본 발명의 일 양태에 따른 하이브리드 경화형 폴리실록산 조성물은 상온과 같은 낮은 온도에서도 경화가 가능하여, 경화 시에 가열이 필요하지 않기 때문에 전기, 전자 장치의 밀봉제, 접착제 또는 코팅제로서 사용될 수 있을 뿐만 아니라, 공정 설비 및 제조 공정의 간소화가 가능하여 경제성을 향상시킬 수 있다.The production of the polysiloxane cured film according to an aspect of the present invention may be characterized in that it is performed at 10 to 50 ° C, preferably 10 to 30 ° C, more preferably 20 to 30 ° C. That is, since the hybrid curable polysiloxane composition according to one aspect of the present invention can be cured even at a low temperature such as room temperature and does not require heating during curing, it can be used as a sealant, adhesive or coating agent for electrical and electronic devices. In addition, it is possible to simplify process equipment and manufacturing processes, thereby improving economic feasibility.
본 발명의 일 양태에 따른 상기 단계 (A)에서 통상의 도포방법을 이용할 수 있으며, 일 구체예로 스프레이법, 롤코터법, 회전도포법, 스핀코터법 등을 들 수 있으나 이에 한정되지 않는다. 또한, 상기 기판은 실리콘, 석영, 유리, 실리콘 웨이퍼, 고분자, 금속 및 금속 산화물 등을 사용할 수 있으며, 이에 한정되지 않는다.In the step (A) according to one aspect of the present invention, a conventional coating method may be used, and one specific example may include a spray method, a roll coater method, a spin coater method, a spin coater method, and the like, but is not limited thereto. In addition, silicon, quartz, glass, silicon wafers, polymers, metals and metal oxides may be used as the substrate, but is not limited thereto.
또한, 상기 상대습도는 30 내지 90%일 수 있고, 좋게는 40 내지 90%, 더욱 좋게는 50 내지 80%일 수 있다. 상술한 습도 조건에서, 수분에 의한 경화 반응이 더욱 용이하게 진행될 수 있다.In addition, the relative humidity may be 30 to 90%, preferably 40 to 90%, and more preferably 50 to 80%. Under the above-described humidity conditions, the curing reaction by moisture can proceed more easily.
본 발명의 일 양태에 따른 상기 단계 (B)단계에서 광경화를 위한 광소스는 가시광선, 자외선, 원자외선, 전자선, 엑스선 등에서 선택될 수 있으며, 일 구체예로, 상기 자외선은 g선(파장: 436㎚), h선, i선(파장: 365㎚) 등을 사용할 수 있으며, 이들 자외선의 조사량은 필요에 따라 적절히 선택될 수 있음은 물론이다. 더욱 구체적으로, 상기 광조사는 고압수은램프를 이용하여 수행될 수 있다.A light source for photocuring in step (B) according to an aspect of the present invention may be selected from visible light, ultraviolet light, far ultraviolet light, electron beam, X-ray, etc., and in one embodiment, the ultraviolet light is g-ray (wavelength : 436 nm), h-rays, i-rays (wavelength: 365 nm), etc., and the irradiation amount of these ultraviolet rays can be appropriately selected as needed. More specifically, the light irradiation may be performed using a high-pressure mercury lamp.
본 발명의 일 양태에 따른 상기 폴리실록산 경화막의 두께는 목적에 따라 적절하게 변경될 수 있음은 물론이나, 바람직하게는 0.1 ㎛ 내지 2,000 ㎛ 두께로 형성될 수 있으며, 좋게는 1 ㎛ 내지 1,000 ㎛, 더욱 좋게는 10 ㎛ 내지 500 ㎛ 두께로 형성될 수 있다.The thickness of the polysiloxane cured film according to one aspect of the present invention may be appropriately changed depending on the purpose, but may be preferably formed to a thickness of 0.1 μm to 2,000 μm, preferably 1 μm to 1,000 μm, and more Preferably, it may be formed to a thickness of 10 μm to 500 μm.
이하는 본 발명의 구체적인 설명을 위하여 일 구현예를 들어 설명하는 바, 본 발명이 하기 구현예에 한정되는 것은 아니다.Hereinafter, an embodiment will be described for detailed description of the present invention, but the present invention is not limited to the following embodiment.
[제조예 1] 상온수분경화형 PDMS(AK-3M)의 제조[Production Example 1] Production of Room Temperature Moisture Curable PDMS (AK-3M)
매커니컬 스터러, 냉각 콘덴서, 질소 주입장치, 및 온도계가 장착된 4구의 3L 반응기를 질소 가스로 충분히 치환하였다. 그 후, 5,000cps의 OH-PDMS(hydroxyl terminated polydimethylsiloxane, YF70C-0.5M) 500g, 20,000cps의 OH-PDMS(YF70C-2M) 1,500g, TMOS(tetramethylorthosilicate) 38.66g을 투입하고 30℃에서 10분 동안 교반하여 충분히 혼합하였다. 상기 혼합물에 소듐 메틸레이트(Sodium Methylate, 30% solution in Methanol) 0.38g을 투입하고, 반응기의 온도를 30℃로 유지하면서 30분간 교반하였다. 상기 반응액 10g을 취한 후, 테트라-n-부틸-티타네이트(tetra-n-butyl titanate, Tyzor TnBT) 반응 시험을 실시하여 히드록시기(hydroxyl functional group)가 존재하지 않음을 확인한 후 반응을 종결하였다. 반응 종결 후, 실온(25℃)에서 99% 폼산(formic acid) 0.11g으로 중화하여 냉각한 뒤에, 고진공 증류하여 미반응 물질을 제거하고 200mesh 철망으로 필터하여, 점도가 15,800 cps 인 상온수분경화형 PDMS 화합물인 AK-3M을 수득하였다. A four-necked 3L reactor equipped with a mechanical stirrer, a cooling condenser, a nitrogen injection device, and a thermometer was sufficiently purged with nitrogen gas. After that, 500 g of OH-PDMS (hydroxyl terminated polydimethylsiloxane, YF70C-0.5M) at 5,000 cps, 1,500 g of OH-PDMS (YF70C-2M) at 20,000 cps, and 38.66 g of TMOS (tetramethylorthosilicate) were added and held at 30 ° C for 10 minutes. Mix thoroughly by stirring. 0.38 g of sodium methylate (30% solution in Methanol) was added to the mixture, and the mixture was stirred for 30 minutes while maintaining the temperature of the reactor at 30°C. After taking 10 g of the reaction solution, a tetra-n-butyl titanate (Tyzor TnBT) reaction test was performed to confirm that there was no hydroxyl functional group, and then the reaction was terminated. After completion of the reaction, it was neutralized with 0.11 g of 99% formic acid at room temperature (25 ° C), cooled, and then filtered by high vacuum distillation to remove unreacted substances and filtered through a 200 mesh wire mesh, and room temperature water curing type PDMS with a viscosity of 15,800 cps. A compound, AK-3M, was obtained.
[제조예 2] 상온수분경화형 PDMS(AK-M2M)의 제조[Production Example 2] Production of Room Temperature Moisture Curable PDMS (AK-M2M)
TMOS(tetramethylorthosilicate) 38.66g 대신에 MTMS(Methyltrimethoxysilane) 27.24 g을 사용한 것을 제외하고는 상기 제조예 1과 동일하게 실시하여 점도가 15,700 cps인 AK-M2M을 수득하였다.AK-M2M having a viscosity of 15,700 cps was obtained in the same manner as in Preparation Example 1, except that 27.24 g of methyltrimethoxysilane (MTMS) was used instead of 38.66 g of tetramethylorthosilicate (TMOS).
[제조예 3] 상온수분경화형 PDMS(AK-V2M)의 제조[Production Example 3] Production of Room Temperature Moisture Curing PDMS (AK-V2M)
TMOS 38.66g 대신에 VTMS(Vinyltrimethoxysilane) 27.24 g을 사용한 것을 제외하고는 상기 제조예 1과 동일하게 실시하여 점도가 16,050 cps 인 AK-V2M을 수득하였다.AK-V2M having a viscosity of 16,050 cps was obtained in the same manner as in Preparation Example 1, except that 27.24 g of VTMS (Vinyltrimethoxysilane) was used instead of 38.66 g of TMOS.
[제조예 4] UV경화형 PDMS(MAT-PDMS)의 제조[Production Example 4] Preparation of UV curable PDMS (MAT-PDMS)
매커니컬 스터러, 냉각 콘덴서, 질소 주입장치, 및 온도계가 장착된 4구의 3L 반응기를 질소 가스로 충분히 치환하였다. 그 후, HT-PDMS(한국바이오젠, RF HD 0080, H content 0.093 mmol/g) 1,000g, AGE(Allyl gylcidyl ether) 11.1g, 백금촉매 10g(1 wt%), 톨루엔 1,000g을 투입하였다. 질소분위기를 유지하면서 130 ℃에서 50분간 교반하였다. FT-IR을 측정하여 Si-H peak(2140 cm-1)가 사라진 것을 확인하고 반응을 종결하여 ET-PDMS을 수득하였다. 그 후, MAA(Methacrylic acid) 8.6g을 투입하고 110 ℃에서 4시간 반응한 후, 미반응물과 용제를 감압 증류하여 제거하고 200mesh 철망으로 필터하여, 점도가 1,100 cps인 MAT-PDMS를 수득하였다. A four-necked 3L reactor equipped with a mechanical stirrer, a cooling condenser, a nitrogen injection device, and a thermometer was sufficiently purged with nitrogen gas. Then, 1,000 g of HT-PDMS (Korea Biogen, RF HD 0080, H content 0.093 mmol/g), 11.1 g of AGE (Allyl gylcidyl ether), 10 g (1 wt%) of platinum catalyst, and 1,000 g of toluene were added. The mixture was stirred at 130 °C for 50 minutes while maintaining a nitrogen atmosphere. FT-IR was measured to confirm that the Si-H peak (2140 cm -1 ) disappeared, and the reaction was terminated to obtain ET-PDMS. Thereafter, 8.6 g of MAA (methacrylic acid) was added and reacted at 110 ° C. for 4 hours. Then, unreacted materials and solvents were distilled off under reduced pressure and filtered through a 200 mesh wire mesh to obtain MAT-PDMS having a viscosity of 1,100 cps.
[제조예 5] UV경화형 PDMS(AT-PDMS)의 제조[Production Example 5] Preparation of UV curable PDMS (AT-PDMS)
MAA 8.6g 대신에 AA(Acrylic acid) 7.2 g을 사용한 것을 제외하고는 상기 제조예 4와 동일하게 실시하여 점도가 1,080 cps인 AT-PDMS를 수득하였다.AT-PDMS having a viscosity of 1,080 cps was obtained in the same manner as in Preparation Example 4, except that 7.2 g of AA (acrylic acid) was used instead of 8.6 g of MAA.
[실시예 1][Example 1]
하이브리드 경화형 폴리실록산 조성물의 제조Preparation of hybrid curable polysiloxane composition
상기 제조예 1에서 제조된 상온수분경화형 PDMS(AK-3M PMDS) 1,955 g과 실리콘오일(PDMS Oil, 100 cPs) 175g을 믹싱탱크에 투입 후, 탱크를 교반기에 장착하고 상온(25℃)에서 30분간 교반한 뒤, 흄드 실리카(KONASIL, K-P15) 250g을 투입하여 30분간 추가로 교반하였다. 그 후, 접착 부여제로 3-아미노프로필트리메톡시실란(3-Aminopropyltrimethoxysilane, ATPMS,) 25g 및 메틸트리메톡시실란(Methyltrimethoxysilane, MTMS) 37.5g을 투입하여 30분간 교반한 뒤에, 알코올 스캐빈저로 헥사메틸디실라잔(Hexamethyldisilazane, HMDZ) 50g, 경화촉매로 디부틸틴디라우레이트(Dibutyltin dilaurate, DBTDL) 7.5g을 투입하여 30분간 교반하였다. 그 후, 상기 제조예 4에서 제조된 UV경화형 PDMS(MAT-PDMS) 100g, 광개시제로 벤질디메틸케탈(Benzyl dimethyl Ketal, BDK) 5g을 투입하고 30분간 교반한 뒤, 신속하게 규정된 카트리지에 포장하여 실시예 1의 하이브리드경화형 폴리실록산 조성물을 수득하였다. 그 물성은 하기 표 2에 기재하였다.After putting 1,955 g of room temperature moisture-curing PDMS (AK-3M PMDS) and 175 g of silicone oil (PDMS Oil, 100 cPs) prepared in Preparation Example 1 into a mixing tank, the tank was mounted on a stirrer and stirred at room temperature (25 ° C) for 30 After stirring for 30 minutes, 250 g of fumed silica (KONASIL, K-P15) was added and further stirred for 30 minutes. After that, 25 g of 3-aminopropyltrimethoxysilane (ATPMS,) and 37.5 g of methyltrimethoxysilane (MTMS) were added as an adhesion imparting agent and stirred for 30 minutes, followed by alcohol scavenger. 50 g of hexamethyldisilazane (HMDZ) and 7.5 g of dibutyltin dilaurate (DBTDL) were added as a curing catalyst and stirred for 30 minutes. Then, 100 g of UV-curable PDMS (MAT-PDMS) prepared in Preparation Example 4 and 5 g of benzyl dimethyl ketal (BDK) as a photoinitiator were added, stirred for 30 minutes, and quickly packaged in a prescribed cartridge. A hybrid curable polysiloxane composition of Example 1 was obtained. The physical properties are listed in Table 2 below.
폴리실록산 경화막의 제조Production of cured polysiloxane film
상대습도 50%, 실온(25℃), 질소분위기 조건에서, 상기에서 제조된 하이브리드 경화형 폴리실록산 조성물을 유리 기판 상에 0.2mm 두께로 코팅하였다. 그 후, 고압 수은 램프(1kW, Philips)로 30초 간 광조사한 뒤, 실온에 방치하여 표면경화시간(ASTM C679) 및 완전경화시간을 측정하고, 폴리실록산 경화막을 제조하였다.Under conditions of a relative humidity of 50%, room temperature (25° C.), and a nitrogen atmosphere, the hybrid curable polysiloxane composition prepared above was coated on a glass substrate to a thickness of 0.2 mm. Then, after light irradiation for 30 seconds with a high-pressure mercury lamp (1 kW, Philips), it was left at room temperature to measure the surface curing time (ASTM C679) and complete curing time, and prepare a polysiloxane cured film.
[실시예 2 내지 6][Examples 2 to 6]
하기 표 1에 기재된 실시예 2 내지 6의 폴리디메틸실록산(PDMS) 화합물 및 광개시제 함량을 사용한 것을 제외하고는, 상기 실시예 1과 동일하게 실시하였으며, 그 물성은 하기 표 2에 기재하였다.Except for using the polydimethylsiloxane (PDMS) compound and the photoinitiator content of Examples 2 to 6 described in Table 1, the same procedure as in Example 1 was performed, and the physical properties are listed in Table 2 below.
[비교예 1][Comparative Example 1]
UV경화형 PDMS(MAT-PDMS) 및 광개시제(BDK)를 사용하지 않은 것을 제외하고는, 상기 실시예 1과 동일하게 실시하여 비교예 1의 상온수분경화형 폴리실록산 조성물을 제조하였으며, 그 물성은 하기 표 2에 기재하였다.A room temperature moisture-curable polysiloxane composition of Comparative Example 1 was prepared in the same manner as in Example 1, except that UV curable PDMS (MAT-PDMS) and photoinitiator (BDK) were not used, and its physical properties are shown in Table 2 below. was described in.
상기 표 2과 같이, 본 발명에 따른 폴리실록산 조성물은 경화 시간이 현저하게 단축됨을 알 수 있다. 구체적으로, 종래의 수분경화형 폴리실록산 조성물은 경화 후에 우수한 물성을 구현할 수 있다 하더라도 경화 속도가 느리며, 기판과의 접착력을 향상시킬 시에 경화막의 경도가 저하되고 표면에 끈적임 현상이 생기는 한계가 있었다. 그러나, 본 발명에 따른 폴리실록산 조성물은 비교예 1과 대비하여, 기존 실록산 경화막의 우수한 물성을 확보함과 동시에 경화 속도가 현저히 향상될 수 있음을 알 수 있다.As shown in Table 2, it can be seen that the curing time of the polysiloxane composition according to the present invention is remarkably shortened. Specifically, even if the conventional moisture-curable polysiloxane composition can implement excellent physical properties after curing, the curing speed is slow, and the hardness of the cured film decreases and stickiness occurs on the surface when improving the adhesion with the substrate. There was a limit. However, compared to Comparative Example 1, the polysiloxane composition according to the present invention secures excellent physical properties of the existing cured siloxane film and at the same time, it can be seen that the curing speed can be significantly improved.
즉, 본 발명에 따른 하이브리드 경화형 폴리실록산 조성물은 공정시간의 단축이 가능하고, 원가를 절감할 수 있어 경제성을 향상시킬 수 있으며, 대량생산에 적용이 용이할 수 있고, 이로부터 제조된 경화막의 접착력 및 물리적 물성을 동시에 만족할 수 있다.That is, the hybrid curable polysiloxane composition according to the present invention can shorten the process time, reduce cost, improve economic feasibility, and can be easily applied to mass production, and the adhesive strength and Physical properties can be satisfied at the same time.
Claims (20)
[화학식 1]
상기 화학식 1에서,
R1은 (C1-C10)알킬 또는 (C2-C10)알케닐이고;
R2는 (C1-C10)알킬이고;
a는 0 또는 1의 정수이다.(a) an alkoxy-terminated polydialkylsiloxane having a terminal group represented by Formula 1 below; (b) a polydialkylsiloxane having a terminal group including a (meth)acrylate group and a hydroxyl group; (c) a curing catalyst; And (d) a photoinitiator; comprising a hybrid curable polysiloxane composition.
[Formula 1]
In Formula 1,
R 1 is (C1-C10)alkyl or (C2-C10)alkenyl;
R 2 is (C1-C10)alkyl;
a is an integer of 0 or 1;
25℃의 온도에서 브룩필드 점도계로 측정한 상기 (a)알콕시말단 폴리디알킬실록산의 점도는 1,000 내지 80,000 cps이고, (b)폴리디알킬실록산의 점도는 100 내지 30,000cps인, 하이브리드 경화형 폴리실록산 조성물.According to claim 1,
(a) the viscosity of the alkoxy-terminated polydialkylsiloxane is 1,000 to 80,000 cps, and (b) the viscosity of the polydialkylsiloxane is 100 to 30,000 cps, as measured by a Brookfield viscometer at a temperature of 25 ° C., hybrid curable polysiloxane composition .
상기 (a)알콕시 말단 폴리디알킬실록산은 하기 화학식 2로 표시되는 것인, 하이브리드 경화형 폴리실록산 조성물.
[화학식 2]
상기 화학식 2에서,
R1은 (C1-C6)알킬 또는 (C2-C6)알케닐이고;
R2 내지 R4는 각각 독립적으로 (C1-C6)알킬이고;
a는 0 또는 1의 정수이고;
n은 1 내지 2,000의 실수이다.According to claim 1,
The (a) alkoxy-terminated polydialkylsiloxane is a hybrid curable polysiloxane composition represented by Formula 2 below.
[Formula 2]
In Formula 2,
R 1 is (C1-C6)alkyl or (C2-C6)alkenyl;
R 2 to R 4 are each independently (C1-C6)alkyl;
a is an integer of 0 or 1;
n is a real number from 1 to 2,000.
상기 (b)(메타)아크릴레이트기 및 히드록시기를 포함하는 말단기는 하기 화학식 3으로 표시되는 것인, 하이브리드 경화형 폴리실록산 조성물.
[화학식 3]
상기 화학식 3에서,
R5는 수소 또는 (C1-C6)알킬이다.According to claim 1,
The (b) (meth) terminal group including an acrylate group and a hydroxyl group is represented by the following formula (3), a hybrid curable polysiloxane composition.
[Formula 3]
In Formula 3,
R 5 is hydrogen or (C1-C6)alkyl.
상기 (b)폴리디알킬실록산은 하기 화학식 4로 표시되는 것인, 하이브리드 경화형 폴리실록산 조성물.
[화학식 4]
상기 화학식 4에서,
R5는 수소 또는 (C1-C6)알킬이고;
R11 내지 R16은 각각 독립적으로 (C1-C6)알킬이고;
p는 1 내지 2,000의 실수이다.According to claim 1,
The (b) polydialkylsiloxane is a hybrid curable polysiloxane composition represented by Formula 4 below.
[Formula 4]
In Formula 4,
R 5 is hydrogen or (C1-C6)alkyl;
R 11 to R 16 are each independently (C1-C6)alkyl;
p is a real number from 1 to 2,000.
상기 하이브리드 경화형 폴리실록산 조성물은 접착 부여제를 더 포함하는 것인, 하이브리드 경화형 폴리실록산 조성물.According to claim 1,
The hybrid curable polysiloxane composition further comprises an adhesion imparting agent, the hybrid curable polysiloxane composition.
상기 접착 부여제는 아민기, 티올기 및 히드록시기에서 선택되는 하나 또는 둘 이상의 반응기를 가지는 알콕시실란; 디알킬디알콕시실란; 알킬트리알콕시실란; 및 테트라알콕시실란;에서 선택되는 것인 하나 또는 둘 이상인, 하이브리드 경화형 폴리실록산 조성물.According to claim 6,
The adhesion imparting agent is an alkoxysilane having one or two or more reactive groups selected from an amine group, a thiol group and a hydroxyl group; dialkyldialkoxysilane; alkyltrialkoxysilanes; And tetraalkoxysilane; one or two or more that are selected from, hybrid curable polysiloxane composition.
상기 하이브리드 경화형 폴리실록산 조성물은 흄드 실리카를 더 포함하는 것인, 하이브리드 경화형 폴리실록산 조성물.According to claim 1,
The hybrid curable polysiloxane composition further comprises fumed silica, the hybrid curable polysiloxane composition.
상기 하이브리드 경화형 폴리실록산 조성물은 흄드 실리카를 더 포함하는 것인, 하이브리드 경화형 폴리실록산 조성물.According to claim 6,
The hybrid curable polysiloxane composition further comprises fumed silica, the hybrid curable polysiloxane composition.
상기 (c)경화촉매는 유기주석화합물, 유기아연화합물, 유기니켈화합물, 지르코늄 착체, 알루미늄 착체, 및 티타늄 착체에서 선택되는 하나 또는 둘 이상인, 하이브리드 경화형 폴리실록산 조성물.According to claim 1,
The (c) curing catalyst is one or two or more selected from organic tin compounds, organic zinc compounds, organic nickel compounds, zirconium complexes, aluminum complexes, and titanium complexes, hybrid curable polysiloxane composition.
상기 (d)광개시제는 아세토페논계 화합물, 벤조페논계 화합물, 트리아진계 화합물, 벤조인계 화합물, 이미다졸계 화합물, 크산톤계 화합물, 포스핀계 화합물 및 옥심계 화합물에서 선택되는 하나 또는 둘 이상인, 하이브리드 경화형 폴리실록산 조성물.According to claim 1,
The (d) photoinitiator is one or two or more selected from acetophenone-based compounds, benzophenone-based compounds, triazine-based compounds, benzoin-based compounds, imidazole-based compounds, xanthone-based compounds, phosphine-based compounds and oxime-based compounds, hybrid curing type A polysiloxane composition.
상기 (a)알콕시 말단 폴리디알킬실록산 100중량부에 대하여, (b)폴리디알킬실록산 1 내지 20 중량부, (c)경화촉매 0.05 내지 2 중량부, 및 (d)광개시제 0.05 내지 1 중량부를 포함하는 것인, 하이브리드 경화형 폴리실록산 조성물.According to claim 1,
(a) 100 parts by weight of alkoxy-terminated polydialkylsiloxane, (b) 1 to 20 parts by weight of polydialkylsiloxane, (c) 0.05 to 2 parts by weight of curing catalyst, and (d) 0.05 to 1 part by weight of photoinitiator A hybrid curable polysiloxane composition comprising:
상기 (a)알콕시 말단 폴리디알킬실록산 100중량부에 대하여, 접착 부여제 0.1 내지 5 중량부를 포함하는 것인, 하이브리드 경화형 폴리실록산 조성물.According to claim 12,
The hybrid curable polysiloxane composition comprising 0.1 to 5 parts by weight of an adhesion imparting agent based on 100 parts by weight of the (a) alkoxy-terminated polydialkylsiloxane.
상기 (a)알콕시 말단 폴리디알킬실록산 100중량부에 대하여, 흄드 실리카 1 내지 20 중량부를 포함하는 것인, 하이브리드 경화형 폴리실록산 조성물.According to claim 12,
The hybrid curable polysiloxane composition comprising 1 to 20 parts by weight of fumed silica based on 100 parts by weight of the (a) alkoxy-terminated polydialkylsiloxane.
상기 하이브리드 경화형 폴리실록산 조성물은 무수 상태인, 하이브리드 경화형 폴리실록산 조성물.According to claim 1,
The hybrid curable polysiloxane composition is an anhydrous state, hybrid curable polysiloxane composition.
(B)광조사를 통해 광경화 및 수분경화하는 단계;를 포함하는, 폴리실록산 경화막의 제조방법.(A) applying the hybrid curable polysiloxane composition of any one of claims 1 to 15 to a substrate at a relative humidity of 30 to 90%; and
(B) photo-curing and moisture-curing through light irradiation; a method for producing a polysiloxane cured film comprising the steps.
상기 단계 (A)의 도포단계 및 (B)의 경화단계는 10 내지 50℃에서 수행되는 것인, 폴리실록산 경화막의 제조방법.According to claim 17,
The coating step of step (A) and the curing step of (B) are carried out at 10 to 50 ° C., a method for producing a polysiloxane cured film.
상기 광조사는 고압수은램프를 이용하여 수행되는 것인, 폴리실록산 경화막의 제조방법.According to claim 17,
The light irradiation is performed using a high-pressure mercury lamp, a method for producing a polysiloxane cured film.
An electronic device comprising the polysiloxane cured film of claim 16.
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| KR20120081719A (en) * | 2011-01-12 | 2012-07-20 | 정우화인 주식회사 | Silicone-epoxy-vinyl resin useful for dispersion and coupling of fillers and method of producing the same |
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