CN113402911B - Silicone coating agent composition and article - Google Patents
Silicone coating agent composition and article Download PDFInfo
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- CN113402911B CN113402911B CN202110280617.3A CN202110280617A CN113402911B CN 113402911 B CN113402911 B CN 113402911B CN 202110280617 A CN202110280617 A CN 202110280617A CN 113402911 B CN113402911 B CN 113402911B
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- silicone coating
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- 239000000203 mixture Substances 0.000 title claims abstract description 71
- 239000004447 silicone coating Substances 0.000 title claims abstract description 48
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 239000003960 organic solvent Substances 0.000 claims abstract description 12
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 10
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 8
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 7
- -1 organosilane compound Chemical class 0.000 claims description 56
- 238000006482 condensation reaction Methods 0.000 claims description 24
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 12
- 239000013522 chelant Substances 0.000 claims description 12
- 229910052782 aluminium Inorganic materials 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 10
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 9
- 239000007809 chemical reaction catalyst Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000010936 titanium Substances 0.000 claims description 9
- 229910052719 titanium Inorganic materials 0.000 claims description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000005372 silanol group Chemical group 0.000 claims description 8
- 239000012298 atmosphere Substances 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 239000008199 coating composition Substances 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 3
- 229910000077 silane Inorganic materials 0.000 claims description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims 1
- 239000007789 gas Substances 0.000 abstract description 24
- 239000000758 substrate Substances 0.000 abstract description 23
- 238000005260 corrosion Methods 0.000 abstract description 17
- 230000007797 corrosion Effects 0.000 abstract description 16
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract description 10
- 229910000037 hydrogen sulfide Inorganic materials 0.000 abstract description 10
- 238000005452 bending Methods 0.000 abstract description 7
- 238000003860 storage Methods 0.000 abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 abstract description 5
- 239000011593 sulfur Substances 0.000 abstract description 5
- 150000003568 thioethers Chemical class 0.000 abstract description 3
- 239000011248 coating agent Substances 0.000 description 20
- 238000001723 curing Methods 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000000576 coating method Methods 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000000126 substance Substances 0.000 description 13
- 230000035699 permeability Effects 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 229920001296 polysiloxane Polymers 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 6
- 239000012847 fine chemical Substances 0.000 description 6
- 229920002050 silicone resin Polymers 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- OLLFKUHHDPMQFR-UHFFFAOYSA-N dihydroxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](O)(O)C1=CC=CC=C1 OLLFKUHHDPMQFR-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- 239000010953 base metal Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 229920002379 silicone rubber Polymers 0.000 description 4
- 125000003944 tolyl group Chemical group 0.000 description 4
- 239000012855 volatile organic compound Substances 0.000 description 4
- 125000005023 xylyl group Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000000068 chlorophenyl group Chemical group 0.000 description 3
- GBFVZTUQONJGSL-UHFFFAOYSA-N ethenyl-tris(prop-1-en-2-yloxy)silane Chemical compound CC(=C)O[Si](OC(C)=C)(OC(C)=C)C=C GBFVZTUQONJGSL-UHFFFAOYSA-N 0.000 description 3
- 125000001207 fluorophenyl group Chemical group 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 description 3
- 239000004945 silicone rubber Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- XPFOWMOZUAQIJW-UHFFFAOYSA-N CC(CC(NC(=N)N)(C)C)([Si](OC)(OC)OC)C Chemical compound CC(CC(NC(=N)N)(C)C)([Si](OC)(OC)OC)C XPFOWMOZUAQIJW-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
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000005336 allyloxy group Chemical group 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- RBSBUSKLSKHTBA-UHFFFAOYSA-N dihydroxy-methyl-phenylsilane Chemical compound C[Si](O)(O)C1=CC=CC=C1 RBSBUSKLSKHTBA-UHFFFAOYSA-N 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- XBIUWALDKXACEA-UHFFFAOYSA-N 3-[bis(2,4-dioxopentan-3-yl)alumanyl]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)[Al](C(C(C)=O)C(C)=O)C(C(C)=O)C(C)=O XBIUWALDKXACEA-UHFFFAOYSA-N 0.000 description 1
- SOYBEXQHNURCGE-UHFFFAOYSA-N 3-ethoxypropan-1-amine Chemical compound CCOCCCN SOYBEXQHNURCGE-UHFFFAOYSA-N 0.000 description 1
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-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
- OYHQOLUKZRVURQ-HZJYTTRNSA-M 9-cis,12-cis-Octadecadienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O OYHQOLUKZRVURQ-HZJYTTRNSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 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
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- NBJODVYWAQLZOC-UHFFFAOYSA-L [dibutyl(octanoyloxy)stannyl] octanoate Chemical compound CCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCC NBJODVYWAQLZOC-UHFFFAOYSA-L 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical group CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-M crotonate Chemical compound C\C=C\C([O-])=O LDHQCZJRKDOVOX-NSCUHMNNSA-M 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- XCLIHDJZGPCUBT-UHFFFAOYSA-N dimethylsilanediol Chemical compound C[Si](C)(O)O XCLIHDJZGPCUBT-UHFFFAOYSA-N 0.000 description 1
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- AVHQYNBSFNOKCT-UHFFFAOYSA-N ethyl-dihydroxy-phenylsilane Chemical compound CC[Si](O)(O)C1=CC=CC=C1 AVHQYNBSFNOKCT-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QZLKVQRFTHKQKP-UHFFFAOYSA-N hexadecanoic acid;tin Chemical compound [Sn].CCCCCCCCCCCCCCCC(O)=O QZLKVQRFTHKQKP-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 229940049918 linoleate Drugs 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- KYCGURZGBKFEQB-UHFFFAOYSA-N n',n'-dibutylpropane-1,3-diamine Chemical compound CCCCN(CCCC)CCCN KYCGURZGBKFEQB-UHFFFAOYSA-N 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- NAQQTJZRCYNBRX-UHFFFAOYSA-N n-pentan-3-ylidenehydroxylamine Chemical group CCC(CC)=NO NAQQTJZRCYNBRX-UHFFFAOYSA-N 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CYCFYXLDTSNTGP-UHFFFAOYSA-L octadecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CYCFYXLDTSNTGP-UHFFFAOYSA-L 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 239000006259 organic additive Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 125000005375 organosiloxane group Chemical group 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
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- XGIZTLFJCDBRDD-UHFFFAOYSA-N phenyl-tris(prop-1-en-2-yloxy)silane Chemical compound CC(=C)O[Si](OC(C)=C)(OC(C)=C)C1=CC=CC=C1 XGIZTLFJCDBRDD-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 239000010454 slate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/08—Anti-corrosive paints
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
Abstract
The present invention provides a silicone coating agent composition which does not contain an organic solvent, has excellent storage stability, is rapidly cured at normal temperature after being coated on a substrate, can form a cured film which has excellent transparency, adhesion and the like and excellent follow-up property to the bending of the substrate, can improve the corrosion resistance of the substrate, and particularly can reduce the formation of sulfides caused by hydrogen sulfide which is a sulfur-containing gas. A silicone coating agent composition comprising: (A) A hydrolyzable group-containing organotrisiloxane compound represented by the following formula (1): 100 parts by mass of the components in the total mass,(R 1、R3 is an unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, R 2 is an unsubstituted, halogen-substituted or alkyl-substituted phenyl group, X is a hydrolyzable group selected from the group consisting of an unsubstituted or alkoxy-substituted alkoxy group, an aryloxy group, an alkenyloxy group, an acyloxy group and a ketoxime group, a is 0 or 1.) (B) a curing catalyst: 0.01 to 10 parts by mass.
Description
Technical Field
The present invention relates to a moisture-curable room-temperature curable silicone coating composition and the like that crosslink-cure by hydrolysis-condensation reaction with moisture (moisture) in the atmosphere at room temperature (23±15 ℃), and particularly relates to a silicone coating composition and the like used for electric-electronic parts, structural material parts and the like. The silicone coating agent composition of the present invention has excellent storage stability, cures rapidly at room temperature after being applied to various substrates, and can provide a cured film having excellent transparency, flexibility (following the bending of the substrate), adhesion (adhesion to the substrate), gas permeability, and the like, and therefore can be a silicone coating agent composition capable of imparting various functional properties such as surface protection, water repellency, rust resistance, water resistance, weather resistance, chemical resistance, and stain resistance to various substrates.
Background
Unlike other organic resins such as hydrocarbon-based resins, silicone resins (organopolysiloxane resins) are excellent in heat resistance, weather resistance, water resistance, flame retardancy, and the like, and can form a cured coating film having a surface with high hardness, and therefore curable silicone rubber compositions (silicone elastomer compositions) having a crosslinkable group such as an alkoxy group or a silanol group bonded to a silicon atom in a molecule, and silicone resin-based resins (polyorganosilsesquioxane resins having a three-dimensional network structure, and the like) are widely used in applications and fields such as surface protective materials for various substrates, heat-resistant paints, weather-resistant paints, water repellents, and various binders. Among them, silicone resins are used for conformal coatings of electronic substrates such as home electric appliances and electronic parts because they are excellent in heat resistance and electrical insulation. In addition, by designing the resin composition, a coating composition that does not require dilution of an organic solvent is also possible, and a coating agent that is excellent in VOC (volatile organic compound) problem/safety has been marketed. However, a general silicone rubber-based or silicone resin-based coating composition has a low effect of protecting an electrode metal (particularly, a silver electrode) against corrosive gases such as hydrogen sulfide.
In order to reduce metal corrosion caused by corrosive gases such as hydrogen sulfide, an acrylic resin-based or urethane resin-based coating agent has to be used, but such an organic resin-based coating material is generally used in a diluted state with an organic solvent, and has problems of VOC and safety. In addition, there is a limit in the range of application of acrylic and urethane-based coating agents due to problems of heat resistance and electrical characteristics.
From the above, there is a demand for a solvent-free silicone-based coating agent which is excellent in heat resistance and electrical characteristics, and also in the ability to prevent metal corrosion by corrosive gases such as hydrogen sulfide.
The present invention is a type of material that forms a hard coating film after curing in a silicone-based coating agent, but as such a silicone coating agent composition, a so-called silicone varnish solution in which a curable silicone resin having a terminal silanol group and an average molecular weight of about 3000 to 2000000 is dissolved in an organic solvent such as toluene or xylene has been used in many cases. When this is used, a film excellent in surface hardness, adhesion, heat resistance, weather resistance, water resistance, etc. can be obtained, but since an organic solvent is used as an essential component and a dehydration condensation crosslinking reaction between silanol groups is used, it is generally necessary to heat cure the film at 150 ℃ or higher for a long period of time.
In view of this, there is a need for a one-pack (one-pack) solvent-free room temperature curable silicone coating composition which is free of organic solvents, curable at room temperature, and excellent in storage stability, and the use of a relatively low molecular weight silicone alkoxy oligomer obtained by partially (co) hydrolytic condensation of an organoalkoxysilane has been studied, and a technique of a cited document has been proposed by actively conducting studies on a curing catalyst which effectively promotes a hydrolysis reaction and a dealcoholization condensation reaction of the silicone alkoxy oligomer due to moisture and formation of a crosslinked film due to siloxane bonds (patent documents 1 and 2: japanese unexamined patent publication No. 60-233264 and Japanese patent publication No. 4110402).
However, all of the techniques are that the cured film obtained is poor in rigidity and flexibility, and therefore, has poor following property against bending of the substrate, and further, cannot prevent metal corrosion due to hydrogen sulfide.
On the other hand, examples of the technique for preventing corrosion of a base metal by a sulfur-containing corrosive gas in a solvent-free silicone composition include a technique in which a metal powder such as silver or copper is added to the composition and the base metal corrosion is reduced by sacrificial corrosion with the metal powder (patent documents 3 and 4: japanese patent publication No. 4114037 and japanese patent publication No. 4530137); a technique for reducing corrosion of a base metal by using an organic additive (patent document 5: japanese patent No. 6418115). These are excellent techniques, but the effect is insufficient as a means for making the corrosive gas species that intrude into the silicone coating harmless by utilizing the reaction inside the coating, depending on the kind of corrosive gas.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open No. 60-233464
Patent document 2: japanese patent No. 4110402
Patent document 3: japanese patent No. 4114037
Patent document 4: japanese patent No. 4530137
Patent document 5: japanese patent No. 6418115
Disclosure of Invention
Problems to be solved by the invention
The present invention has been made to solve the above-described drawbacks, and an object of the present invention is to provide a silicone coating composition which does not contain an organic solvent, does not impair the original characteristics of a curable silicone compound, is excellent in storage stability as a coating composition, is rapidly cured at normal temperature after being applied to a substrate, can form a cured film excellent in transparency, adhesion and the like, and is excellent in follow-up property (flexibility) to the bending of the substrate, and can improve the corrosion resistance of the substrate due to low gas permeability, and in particular, can reduce the formation of sulfides caused by hydrogen sulfide as a sulfur-containing gas (sulfur-containing gas).
Means for solving the problems
The present inventors have conducted intensive studies in order to achieve the above object, and as a result, have found that: the present invention has been completed by using an organosilicon coating composition having a condensation reaction curing property, which is represented by the following general formula (1), and which contains an organotrisiloxane compound having a specific molecular structure having at least 1 unsubstituted or substituted phenyl group in the molecule and having at least 4, preferably 4 to 6 hydrolyzable groups in the molecule, as a main agent, and which contains a curing catalyst, and which exhibits excellent preservability under sealing and is rapidly cured by a hydrolytic condensation reaction by moisture in an atmosphere under an open atmosphere, and by which a cured coating film having excellent transparency, adhesiveness and the like and excellent following property (flexibility) against bending of a substrate can be provided, and by which the cured coating film can reduce formation of sulfides by hydrogen sulfide due to low gas permeability.
That is, the present invention provides the following silicone coating agent composition and an article sealed, coated, fixed or bonded with a cured product of the composition.
[1] A silicone coating agent composition comprising:
(A) An organotrisiloxane compound containing a hydrolyzable group represented by the following general formula (1): 100 parts by mass of the components in the total mass,
[ Chemical formula 1]
(Wherein R 1、R3 is an unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, R 2 is an unsubstituted, halogen-substituted or alkyl-substituted phenyl group, and X is a hydrolyzable group of at least one selected from the group consisting of an unsubstituted or alkoxy-substituted alkoxy group, an aryloxy group, an alkenyloxy group, an acyloxy group and a ketoxime group, a is independently 0 or 1 for each bonded silicon atom.)
(B) Curing catalyst: 0.01 to 10 parts by mass.
[2] The silicone coating composition of [1], wherein, in the general formula (1), R 3 is an unsubstituted, halogen-substituted or alkyl-substituted phenyl group.
[3] The silicone coating composition of [1] or [2], wherein in the general formula (1), X is methoxy, ethoxy, isopropoxy or ketoxime group.
[4] The silicone coating composition according to any one of [1] to [3], further comprising 0.1 to 100 parts by mass of a hydrolyzable organosilane compound represented by the following general formula (2) excluding the component (A) and/or a partial hydrolytic condensate (C) thereof, per 100 parts by mass of the component (A).
(R1)aSi(X)(4-a) (2)
(Wherein R 1 and X, a are the same as defined above.)
[5] The silicone coating composition according to any one of [1] to [4], which does not contain an organic solvent.
[6] The silicone coating composition according to any one of [1] to [5], wherein component (A) is a hydrolysis-condensation reaction product of a hydrolyzable organosilane compound represented by the following general formula (2) and a diorganosilanediol represented by the following general formula (3).
(R1)aSi(X)(4-a) (2)
(Wherein R 1 and X, a are the same as defined above.)
[ Chemical formula 2]
(Wherein R 2、R3 is the same as described above respectively.)
[7] An article sealed, coated, fixed or bonded with the cured product of the silicone coating agent composition of any one of [1] to [6 ].
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, a silicone coating composition is obtained which has excellent storage stability, can be applied to a substrate even without containing an organic solvent, and can rapidly form a cured film at room temperature after application, wherein the cured film has excellent transparency, adhesion, and the like, and can provide a cured film having excellent follow-up properties (flexibility) with respect to bending of the substrate, and has low gas permeability, so that the corrosion resistance of the substrate is improved, and particularly, sulfide formation (sulfiding) due to hydrogen sulfide as a sulfur-containing gas can be reduced.
Detailed Description
The present invention will be described in detail below.
[ (A) component ]
(A) The component (a) which becomes the main component of the silicone coating composition of the present invention is an organotrisiloxane compound having a specific molecular structure represented by the following general formula (1), having at least 1 unsubstituted or substituted phenyl group in the molecule, and containing at least 4, preferably 4 to 6 hydrolyzable groups in the molecule.
(A) The component (c) is rapidly crosslinked and cured by moisture (moisture) in the atmosphere at room temperature (23±15 ℃ and the same temperature) by hydrolysis-condensation reaction in the presence of a curing catalyst of component (B) described later, and a cured film excellent in transparency, adhesion and the like, excellent in follow-up property (flexibility) to the bending of the substrate and suppressed in gas permeability can be formed.
[ Chemical 3]
(Wherein R 1、R3 is an unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, R 2 is an unsubstituted, halogen-substituted or alkyl-substituted phenyl group, X is a hydrolyzable group of at least one selected from the group consisting of an unsubstituted or alkoxy-substituted alkoxy group, an aryloxy group, an alkenyloxy group, an acyloxy group and a ketoxime group, a is independently 0 or 1 for each bonded silicon atom.)
In the above formula (1), R 1、R3 is each independently an unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, examples thereof include straight-chain, branched or cyclic alkyl groups having 1 to 10 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, neopentyl, hexyl, cyclohexyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl and the like, straight-chain, branched or cyclic alkenyl groups having 2 to 10 carbon atoms such as vinyl, allyl, propenyl, isopropenyl, butenyl, isobutenyl, pentenyl, hexenyl, cyclohexenyl and the like, phenyl, tolyl, xylyl, naphthyl and the like, aryl groups having 6 to 10 carbon atoms such as phenyl, tolyl, xylyl, naphthyl and the like an alkylaryl group having 7 to 10 carbon atoms such as a mesityl group, an aralkyl group having 7 to 10 carbon atoms such as a benzyl group and a phenethyl group, a chloromethyl group obtained by substituting a part of hydrogen atoms of these groups with a halogen atom or the like, a 2-bromoethyl group, a 3, 3-trifluoropropyl group, a 3,4, 5-heptafluoropentyl group, a 3,4, 5-heptafluoropentyl group, a catalyst, halogen substituted monovalent hydrocarbon groups such as 2, 3-trifluoro-2-chlorocyclobutyl, 3, 4-dibromo-1-chlorohexyl, difluoro-monochlorovinyl, 2-iodocyclohexenyl, chlorophenyl, perchlorophenyl, fluorophenyl, perfluorophenyl, 2-trifluoromethylphenyl and 2, 4-dibromobenzyl.
Among these, as R 1, methyl, ethyl, propyl, vinyl, and phenyl are preferable, and as described in the following item of R 2, when low gas permeability of the resulting cured film becomes important, phenyl which is unsubstituted, halogen-substituted, or alkyl-substituted is preferable, and other various monovalent organic groups can be selected for the reason of designing the curing rate by the hydrolysis-condensation reaction of the composition of the present invention.
R 3 is preferably an unsubstituted, halogen-substituted or alkyl-substituted phenyl group such as phenyl group, tolyl group, xylyl group, chlorophenyl group, perchlorophenyl group, fluorophenyl group, perfluorophenyl group, 2-trifluorotolyl group or the like, from the viewpoint of reducing the gas permeability of the resulting cured film.
In addition, R 3 is a monovalent hydrocarbon group other than the above-mentioned unsubstituted, halogen-substituted or alkyl-substituted phenyl group, whereby Tg of the cured film can be controlled, and R 3 can be variously designed depending on the low gas permeability and Tg of the object. Among these, alkyl groups, allyl groups, and fluoroalkyl groups are particularly preferable because the cured film obtained is excellent in releasability and water repellency.
In the above formula (1), R 2 is an unsubstituted, halogen-substituted or alkyl-substituted phenyl group, and the organotrisiloxane compound represented by the formula (1) of the component (A) must have at least 1 unsubstituted, halogen-substituted or alkyl-substituted phenyl group in 1 molecule (for example, the above-exemplified phenyl group, tolyl group, xylyl group, chlorophenyl group, perchlorophenyl group, fluorophenyl group, perfluorophenyl group, 2-trifluoromethylphenyl group and the like). In the case where low gas permeability is important, it is preferable to have 2 (i.e., both R 2 and R 3) unsubstituted, halogen substituted or alkyl substituted phenyl groups in the molecule.
By using the unsubstituted or substituted phenyl group, the gas permeability of the cured film is reduced, and in the case of an organotrisiloxane compound having no unsubstituted or substituted phenyl group in the molecule, the gas permeability of the cured film is increased, and corrosion of the base metal by corrosive gas can no longer be reduced.
In the above formula (1), each X is independently a hydrolyzable group of at least one selected from the group consisting of an unsubstituted or alkoxy-substituted alkoxy group, an aryloxy group, an alkenyloxy group, an acyloxy group and a ketoxime group. Specifically, X is preferably a hydrolyzable group selected from at least one of an unsubstituted or alkoxy-substituted alkoxy group having 1 to 7 carbon atoms, an aryloxy group, an alkenyloxy group, an acyloxy group and a ketoxime group, and examples thereof include a C1-6 carbon atom such as methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group and tert-butoxy group, a C3-6 carbon atom such as alkoxy group having 1 to 4 carbon atoms, methoxy-substituted methoxy group, methoxy-substituted ethoxy group, ethoxy-substituted methoxy group and ethoxy-substituted ethoxy group, an alkoxy-substituted alkoxy group having 2 to 4 carbon atoms such as an ethyleneoxy group, allyloxy group, propyleneoxy group, an allyloxy group, an aryloxy group having 2 to 4 carbon atoms such as a butyleneoxy group and a phenoxy group, an acyloxy group having 6 to 10 carbon atoms such as an acetoxy group and propionyloxy group, a C3-6 carbon atoms such as dimethylketoxime group, methylethketoxime group and diethylketoxime group, and the like. Preferred are methoxy, ethoxy, isopropoxy, methyl ethyl ketoxime, and the like.
A is independently 0 or 1, preferably 1, for each bonded silicon atom.
(A) In the above formula (1), the component (c) is an organotrisiloxane compound having a hydrolyzable group and having at least 4, preferably 4 to 6, more preferably 4 hydrolyzable groups X in 1 molecule, and a suitable leaving group can be selected in order to achieve a desired curing rate and storage property.
The organic trisiloxane compound having a hydrolyzable group represented by formula (1) may be specifically exemplified by the compounds shown below.
[ Chemical formula 4]
[ Chemical 5]
Further, by subjecting a hydrolyzable organosilane compound having the above-mentioned R 1 and hydrolyzable group X as 1-valent hydrocarbon groups bonded to silicon atoms represented by the following general formula (2) and a diorganosilane diol (diorganodihydroxy silane) having at least 1, preferably 2 unsubstituted, halogen-substituted or alkyl-substituted phenyl groups in the molecule, each of which has 1 of the above-mentioned R 2 and R 3 as 1-valent hydrocarbon groups bonded to silicon atoms represented by the following general formula (3), to hydrolysis-condensation reaction under conventionally known conditions in the presence of a condensation reaction catalyst, it is possible to easily produce an organotrisiloxane compound containing hydrolyzable groups represented by the above general formula (1) as component (A).
(R1)aSi(X)(4-a) (2)
[ 6] A method for producing a polypeptide
(In each formula, R 1、R2、R3 and X, a are the same as those described above.)
Specific examples of the hydrolyzable organosilane compound represented by the above formula (2) include vinyltrimethoxysilane, phenyltrimethoxysilane, methyltrimethoxysilane, vinyltriethoxysilane, phenyltriethoxysilane, methyltriethoxysilane, vinyltriisopropenyloxysilane, phenyltriisopropenyloxysilane, methyltriethopropenyloxysilane and the like.
Specific examples of the diorganosilane diol represented by the above formula (3) include diphenylsilane diol, methylphenylsilane diol, ethylphenylsilane diol, and the like.
The reaction ratio of the hydrolyzable organosilane compound represented by the formula (2) to the diorganosilanol represented by the formula (3) is preferably 1 mole or more of the hydrolyzable organosilane compound represented by the formula (2) relative to 1 mole of silanol groups in the diorganosilanol represented by the formula (3), and more preferably 2 moles or more of the hydrolyzable organosilane compound relative to 1 mole of the silanol groups in order to reduce residual silanol groups in the reaction product. The upper limit of the reaction molar ratio of the hydrolyzable organosilane compound represented by the formula (2) may be about 5mol or less. If silanol groups remain in the reaction product, the curing reaction rate of the subsequent composition may be lowered.
Examples of the condensation reaction catalyst used in the above reaction include a guanidine group-containing silane compound such as a titanium chelate compound and tetramethylguanidinopropyltrimethoxysilane, an aluminum chelate compound, and an organozirconium compound.
The amount of the condensation reaction catalyst to be added is not particularly limited as long as it is sufficient for the condensation reaction of the diorganosilane diol represented by the above formula (3) and the hydrolyzable organosilane compound represented by the above formula (2) at room temperature to heating, and is usually about 0.01 to 10 parts by mass, particularly about 0.1 to 5 parts by mass, relative to 100 parts by mass of the total of the diorganosilane diol and hydrolyzable organosilane compound.
As the reaction conditions, conditions are employed in which the reaction product ((A) component) can be obtained by removing alcohol or the like by-produced in the condensation reaction and reacting the same at a temperature of about 0 to 150 ℃, particularly about 25 to 100 ℃ for about 5 to 120 minutes, particularly about 10 to 60 minutes.
In the silicone coating composition of the present invention, 1 or 2 or more hydrolyzable group-containing organotrisiloxane compounds of component (a) may be used alone or in combination.
[ (B) component ]
(B) The curing catalyst of the component (a) is a condensation reaction catalyst required for the composition of the present invention to rapidly become a cured film by hydrolysis-condensation reaction with moisture (moisture) in the atmosphere in the curing step of the component (a) containing a hydrolyzable group represented by the above general formula (1), and is selected from organotin compounds, organoaluminum compounds, organotitanium compounds, organozirconium compounds and organic base compounds, and a suitable catalyst is selected according to the reactivity of the hydrolyzable group X selected in the above general formula (1) of the component (a).
Examples of such a condensation reaction catalyst include hydroxides, oxides, and alkali metal salts of alkali metals and alkaline earth metals, and specifically, hydroxides of alkaline earth metals such as calcium hydroxide and magnesium hydroxide, chlorides of alkaline earth metals such as calcium chloride and magnesium chloride, oxides of alkaline earth metals such as calcium oxide and magnesium oxide, alkali zinc carbonate, and alkali metal salts such as alkali magnesium carbonate.
Further, as other condensation reaction catalysts, aluminum chelate compounds, organotitanium compounds, organotin compounds, aminoalkylalkoxysilane, ammonium salts, and the like can also be used. Examples of the aluminum chelate compound include aluminum acetylacetonate diisopropoxylate, aluminum tri (ethylacetate), aluminum tri (ethylacetylacetonate), aluminum bis (ethylacetylacetate), titanium tetra-isopropoxide, titanium tetra-N-butoxide, titanium tetra (2-ethylhexyloxy) and the like, examples of the organic titanium compound include dibutyltin diacetate, dibutyltin dilaurate, dibutyltin dioctoate, stannous octoate, stannous naphthenate, stannous oleate, stannous isobutyrate, stannous linoleate, stannous stearate, stannous benzoate, stannous laurate, stannous o-thymic acid, stannous benzoate, stannous crotonate, stannous topt-bromobenzoate, stannous palmitate, stannous cinnamate, and alkylsulfite such as phenylstannous acetate, examples of the salt include a salt of an acid with an amine, an acetic acid, a formic acid, and the like, and an amine such as allylamine, 2-ethylhexyl amine, allyl amine, and the like, 3-ethoxypropylamine, diisobutylamine, 3-diethylaminopropylamine, di-2-ethylhexylamine, dibutylaminopropylamine, tri-n-octylamine, t-butylamine, sec-butylamine, propylamine, 3-methoxypropylamine, and the like.
The amount of the curing catalyst of the component (B) is 0.01 to 10 parts by mass, particularly preferably 0.02 to 5 parts by mass, based on 100 parts by mass of the hydrolyzable group-containing organotrisiloxane compound of the component (a), from the viewpoint that the reaction proceeds satisfactorily and the curing of the silicone coating composition obtained additionally becomes satisfactory.
[ (C) component ]
The silicone coating composition of the present invention may further contain a hydrolyzable organosilane compound (C) represented by the formula (2) as the component used in the production of the component (a) in addition to the component (a) and the component (B). If the component (C) is compounded, the preservability of the composition can be improved, and the effect of being able to control the curing time (usable time) of the composition can be obtained.
When the hydrolyzable organosilane compound represented by the formula (2) is reacted with the diorganosilanol represented by the formula (3) to obtain the component (a), the hydrolyzable organosilane compound represented by the formula (2) is reacted in excess, and the remaining hydrolyzable organosilane compound represented by the formula (2) after the reaction can be used as it is.
The content of the hydrolyzable organosilane compound represented by the above formula (2) may be 100 parts by mass or less (0 to 100 parts by mass), preferably about 0.1 to 50 parts by mass, per 100 parts by mass of the component (a).
[ Other Components ]
The silicone coating composition of the present invention may further contain, if necessary, a small amount of various additives such as plasticizers, release agents, flame retardants, antioxidants, ultraviolet absorbers, pigments such as titanium dioxide, carbon black, iron oxide, and dyes, in a range not impairing the object of the present invention. In the same manner, fumed silica, silica aerosol, silica gel, and reinforcing silica fillers treated with organosilanes, organosiloxanes, or organosilazanes may be blended within a range that does not impair the object of the present invention, and further fillers such as asbestos, crushed fused quartz, alumina, aluminum silicate, zirconium silicate, magnesium oxide, zinc oxide, talc, diatomaceous earth, mica, calcium carbonate, clay, zirconium oxide, glass, sand, graphite, barium sulfate, zinc sulfate, aluminum powder, sawdust, cork, polymer powder of fluorocarbon, silicone rubber powder, silicone resin powder, and the like may be blended.
Further, if necessary, an organic solvent may be blended, and from the viewpoint of VOC and safety, it is preferable that the composition has a viscosity usable in the process and contains no or little organic solvent.
In the production of the silicone coating composition of the present invention, the components (a) and (B) may be simply mixed in predetermined amounts, and in this case, the temperature at the time of mixing is not limited, and particularly, the silicone coating composition can be easily obtained by stirring and mixing at room temperature for 10 minutes or longer, preferably 10 to 60 minutes without performing an operation such as heating. In addition, in the mixing, it is preferable to carry out the mixing under a nitrogen atmosphere in order to prevent hydrolysis of a hydrolyzable group such as an alkoxy group due to mixing of moisture.
Thus, the silicone coating agent composition of the present invention can provide an article sealed, coated, fixed, or bonded with the cured product of the composition.
The silicone coating composition of the present invention can be applied and cured by a conventionally known method to various metal substrates, wood, stone, plasterboard, slate, tile, concrete, glass, ceramics, plastic products, organic resin coated products, and the like, to form a coating film. In this case, examples of the coating method include brush coating, spray coating, dipping, a flow coater, a blade coater, a spin coater, and the like, and further, in-situ coating may be performed. The coating amount may be generally in the range of 0.1 to 200 μm, preferably 1 to 100 μm, depending on the type of substrate and the purpose of coating.
The curing conditions of the silicone coating composition of the present invention are not particularly limited, and since the composition is cured by moisture in the air to form a coating film, the composition is allowed to stand at a temperature ranging from room temperature to 80 ℃ for about 1 minute to 2 hours, and is dried (tack-free state), and the curing reaction can be completed by standing for several hours to several days.
Thus, the silicone coating agent composition of the present invention can provide an article sealed, coated, fixed, or bonded with the cured product of the composition.
Examples
The present invention will be specifically described below with reference to examples, examples and comparative examples, but the present invention is not limited to the examples. In each example, room temperature represents 25 ℃, and viscosity represents a measured value obtained by a rotational viscometer at 25 ℃.
Preparation example
(A) Composition of the components
(A-1)
Diphenylsilanediol (16.2 g), vinyltrimethoxysilane (25 g), and a titanium chelate catalyst (0.2 g, manufactured by Matsumoto FINE CHEMICAL Co.Ltd., ORGATIX TC-401) were added to a 100ml flask, reacted at 100℃for 60 minutes, and then methanol and residual vinyltrimethoxysilane produced were removed by nitrogen flow, thereby obtaining an organotrisiloxane compound (A-1) represented by the following formula.
[ Chemical 7]
(A-2)
Diphenylsilanediol (16.2 g), phenyltrimethoxysilane (25 g), a titanium chelate catalyst (0.2 g, manufactured by Matsumoto FINE CHEMICAL Co.Ltd., ORGATIX TC-401) were added to a 100ml flask, reacted at 100℃for 60 minutes, and then methanol generated was removed by nitrogen flow, and then the remaining phenyltrimethoxysilane was removed by heating under reduced pressure, thereby obtaining an organotrisiloxane compound (A-2) represented by the following formula.
[ Chemical formula 8]
(A-3)
Diphenylsilanediol (16.2 g), methyltrimethoxysilane (25 g), a titanium chelate catalyst (0.2 g, manufactured by Matsumoto FINE CHEMICAL co.ltd., ORGATIX TC-401) were added to a 100ml flask, reacted at 100 ℃ for 60 minutes, and then methanol and remaining methyltrimethoxysilane produced were removed by nitrogen flow, thereby obtaining an organotrisiloxane compound (a-3) represented by the following formula.
[ Chemical formula 9]
(A-4)
Diphenylsilanediol (16.2 g), vinyltriisopropenoxysilane (25 g), tetramethylguanidinopropyltrimethoxysilane (0.2 g) were added to a 100ml flask, and after reacting them at 100℃for 60 minutes, the acetone produced was removed by nitrogen flow, and then the remaining vinyltriisopropenoxysilane was removed by heating under reduced pressure, thereby obtaining an organotrisiloxane compound (A-4) represented by the following formula.
[ Chemical formula 10]
(A-5)
In a 100ml flask were added methylphenylsilanediol (16.2 g, a part of which had been dimerized), vinyltrimethoxysilane (25 g), a titanium chelate catalyst (0.2 g, manufactured by Matsumoto FINE CHEMICAL co.ltd., ORGATIX TC-401), which was reacted at 100 ℃ for 60 minutes, and then methanol and remaining vinyltrimethoxysilane produced were removed by nitrogen flow, thereby obtaining an organotrisiloxane compound (a-5) represented by the following formula.
[ Chemical formula 11]
(A) Composition (for comparison)
(a-1)
In a 100ml flask were added dimethylsilanediol (12.3 g, a part of which had been dimerized), methyltrimethoxysilane (20 g), a titanium chelate catalyst (0.2 g, manufactured by Matsumoto FINE CHEMICAL co.ltd., ORGATIX TC-401), which was reacted at 100 ℃ for 60 minutes, and then methanol and remaining methyltrimethoxysilane produced were removed by nitrogen flow, thereby obtaining an organotrisiloxane compound (a-1) represented by the following formula.
[ Chemical formula 12]
(a-2)
A100 ml flask was charged with a terminal hydroxyl-type dimethylsiloxane polymer (700 mPa.s, 300 g), methyltrimethoxysilane (25 g), and a titanium chelate catalyst (0.2 g, manufactured by Matsumoto FINE CHEMICAL Co.Ltd., ORGATIX TC-401), which were reacted at 100℃for 60 minutes, and then methanol generated was removed by nitrogen flow, and then the remaining methyltrimethoxysilane was removed by heating under reduced pressure, to thereby obtain an organopolysiloxane compound (a-2) represented by the following formula.
[ Chemical formula 13]
(Wherein n is 250.)
Examples 1 to 5 and comparative examples 1 to 3
The components shown in tables 1 and 2 were mixed in respective mixing amounts in a 10ml glass, and the mixture was manually mixed and stirred at room temperature for 10 minutes to obtain a silicone coating composition. The solvent components (A-1) to (A-5), (a-1) and (a-2) were not contained. The appearance and properties of the obtained silicone coating composition were visually confirmed and are shown in tables 1 and 2.
The silicone coating composition obtained above was cured under curing conditions of 23 ℃/50% rh×7 days. The appearance and properties of the cured product obtained were visually confirmed and are shown in tables 1 and 2.
The raw materials used in the above preparation examples except for the component (A) are shown below.
(B) Composition of the components
(B-1)
Tin catalyst: u-830 (manufactured by Ridong chemical Co., ltd., dioctyltin)
(B-2)
Amine catalyst: tetramethyl guanidine propyl trimethoxy silane
(C) Composition of the components
(C-1)
Vinyl trimethoxy silane
(A) Composition (for comparison)
(a-3)
A solvent-type coating agent mainly composed of an acrylic resin component was prepared: humiseal (registered trademark) -1B66NS. The solid content was 35 mass% (65 mass% of the solvent component), and the film was applied by diluting with an additional solvent (diluent Humiseal (registered trademark) to double the nar 901).
[ Table 1]
[ Table 2]
Next, the cured product appearance, tack-free time, corrosion resistance test and flexibility were evaluated by using the silicone coating agent compositions of the above examples and comparative examples, and comparative example 3 using the above (a-3) component. The results are shown in Table 3.
(Appearance of cured product)
The film cured on the aluminum dish, which was prepared in the following evaluation of tack free time, was visually evaluated for transparency and degree of coloration.
(Tack free time)
The composition (liquid) was applied to an aluminum dish in a square form of 2cm×2cm (4 cm 2) at a concentration of 0.20g, and the time until the adhesiveness to the surface of the composition by finger touch was lost was evaluated as a curing time (tack free time).
(Test for anti-Corrosion Property)
Each material (silicone coating composition) was applied to the surface of a silver-plated aluminum plate in a manner that the cured film became about 200 μm, 0.08g of each composition (liquid) was applied to a square of 2cm×2cm (4 cm 2), and cured under a curing condition of 23 ℃/50% rh×7 days, and the silver-plated surface was observed for corrosion state over time (initial, 1 day later, 3 days later, 7 days later, and 14 days later) using a hydrogen sulfide gas corrosion tester. The etching conditions are as follows.
Concentration of hydrogen sulfide: 2ppm of
Temperature: 23 DEG C
Humidity: 50% Rh
The silver plating surfaces before and after the etching test were observed, and the silver plating surfaces were judged to have corroded at the time of the initial change in silver luster (blackening, graying).
(Flexibility)
When the silver-plated aluminum sheet after the completion of the coating (having a cured film of the silicone coating agent composition) after the completion of the corrosion resistance test was folded, it was evaluated whether the coating could follow the substrate without cracking.
[ Table 3]
(Results)
From the above results, it was confirmed that: the silicone coating composition of the present invention is excellent in curability and transparency at room temperature, and also excellent in the effect of preventing corrosion of a metal substrate by a corrosive gas and in substrate following properties (flexibility).
Claims (9)
1. A moisture-curable silicone coating composition comprising:
(A) A hydrolyzable group-containing organotrisiloxane compound represented by the following general formula (1), which is a hydrolysis-condensation reaction product of a hydrolyzable organosilane compound represented by the following general formula (2) and a diorganosilanediol represented by the following general formula (3): 100 parts by mass of the components in the total mass,
(R1)a Si(X)(4-a)(2)
Wherein R 1, X, a are each as defined in the following general formula (1),
Wherein R 2、R3 is as defined in the following general formula (1) respectively,
Wherein R 1、R3 is an unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, R 2 is an unsubstituted, halogen-substituted or alkyl-substituted phenyl group, X is a hydrolyzable group of at least one selected from the group consisting of an unsubstituted or alkoxy-substituted alkoxy group, an aryloxy group, an alkenyloxy group, an acyloxy group and a ketoxime group, a is 0 or 1 independently for each bonded silicon atom,
(B) A condensation reaction catalyst required for hydrolysis-condensation reaction of component (a) with moisture in the atmosphere, that is, moisture, in the curing step, comprising an organotin compound, an organoaluminum compound, an organotitanium compound, an organozirconium compound or an organoalkali compound: 0.01 to 10 parts by mass.
2. The silicone coating agent composition according to claim 1, wherein, in the general formula (1), R 3 is an unsubstituted, halogen-substituted or alkyl-substituted phenyl group.
3. The silicone coating agent composition according to claim 1 or 2, wherein in the general formula (1), X is methoxy, ethoxy, isopropoxy, or ketoxime group.
4. The silicone coating composition according to claim 1 or 2, further comprising 0.1 to 100 parts by mass of a hydrolyzable organosilane compound represented by the following general formula (2) excluding the component (A) and/or a partial hydrolytic condensate (C) thereof per 100 parts by mass of the component (A),
(R1)a Si(X)(4-a)(2)
Wherein R 1 and X, a are the same as defined above.
5. The silicone coating agent composition according to claim 1 or 2, which does not contain an organic solvent.
6. The silicone coating composition according to claim 1 or 2, wherein the mixing ratio of the hydrolyzable organosilane compound represented by the general formula (2) and the diorganosilanol represented by the general formula (3) is 1mol or more and 5mol or less relative to 1mol of silanol groups in the diorganosilanol represented by the general formula (3).
7. The silicone coating composition according to claim 1 or 2, wherein component (a) is a hydrolysis-condensation reactant using a titanium chelate compound, a guanidine group-containing silane compound, an aluminum chelate compound, or an organozirconium compound as a condensation reaction catalyst.
8. An article sealed, coated, fixed or bonded with the cured product of the silicone coating agent composition according to any one of claims 1 to 7.
9. A process for producing an organosilicon coating composition, wherein a hydrolyzable organosilane compound represented by the following general formula (2) and a diorganosilanol represented by the following general formula (3) are subjected to hydrolysis-condensation reaction in the presence of a condensation catalyst to synthesize a hydrolyzable group-containing organotrisiloxane compound (A) represented by the following general formula (1), (R 1)a Si(X)(4-a) (2)
Wherein R 1, X, a are each as defined in the following general formula (1),
Wherein R 2、R3 is as defined in the following general formula (1) respectively,
Wherein R 1、R3 is an unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, R 2 is an unsubstituted, halogen-substituted or alkyl-substituted phenyl group, X is a hydrolyzable group of at least one selected from the group consisting of an unsubstituted or alkoxy-substituted alkoxy group, an aryloxy group, an alkenyloxy group, an acyloxy group and a ketoxime group, a is 0 or 1 independently for each bonded silicon atom,
Next, this compound (a) and a condensation reaction catalyst (B) necessary for hydrolysis-condensation reaction of the compound (a) including an organotin compound, an organoaluminum compound, an organotitanium compound, an organozirconium compound, or an organoalkali compound with moisture in the atmosphere in the curing step are mixed to obtain a moisture-curable silicone coating composition.
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| CN101142222A (en) * | 2005-03-15 | 2008-03-12 | 陶氏康宁东丽株式会社 | Organotrisiloxane, preparation and use in curable resin composition |
| CN101942288A (en) * | 2010-09-16 | 2011-01-12 | 陈俊光 | Method for preparing silicon rubber adhesive cured at room temperature |
| CN102902162A (en) * | 2007-12-14 | 2013-01-30 | 旭化成电子材料株式会社 | Photosensitive resin composition |
| JP2019026606A (en) * | 2017-08-01 | 2019-02-21 | 信越化学工業株式会社 | Siloxane compound, and method of producing the same |
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| CN101142222A (en) * | 2005-03-15 | 2008-03-12 | 陶氏康宁东丽株式会社 | Organotrisiloxane, preparation and use in curable resin composition |
| CN102902162A (en) * | 2007-12-14 | 2013-01-30 | 旭化成电子材料株式会社 | Photosensitive resin composition |
| CN101942288A (en) * | 2010-09-16 | 2011-01-12 | 陈俊光 | Method for preparing silicon rubber adhesive cured at room temperature |
| JP2019026606A (en) * | 2017-08-01 | 2019-02-21 | 信越化学工業株式会社 | Siloxane compound, and method of producing the same |
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