CN113402911A - Silicone coating agent composition and article - Google Patents
Silicone coating agent composition and article Download PDFInfo
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- CN113402911A CN113402911A CN202110280617.3A CN202110280617A CN113402911A CN 113402911 A CN113402911 A CN 113402911A CN 202110280617 A CN202110280617 A CN 202110280617A CN 113402911 A CN113402911 A CN 113402911A
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- coating agent
- agent composition
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- 239000000203 mixture Substances 0.000 title claims abstract description 65
- 239000004447 silicone coating Substances 0.000 title claims description 39
- 239000003795 chemical substances by application Substances 0.000 title claims description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 9
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 7
- 239000008199 coating composition Substances 0.000 claims abstract description 4
- 229920003169 water-soluble polymer Polymers 0.000 claims abstract description 3
- -1 isopropenyloxy group Chemical group 0.000 claims description 52
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims 1
- 239000011248 coating agent Substances 0.000 abstract description 44
- 238000000576 coating method Methods 0.000 abstract description 37
- 239000007789 gas Substances 0.000 abstract description 24
- 239000000758 substrate Substances 0.000 abstract description 20
- 238000005260 corrosion Methods 0.000 abstract description 18
- 230000007797 corrosion Effects 0.000 abstract description 18
- 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
- 238000003860 storage Methods 0.000 abstract description 8
- 238000005452 bending Methods 0.000 abstract description 7
- 125000004423 acyloxy group Chemical group 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
- 238000001723 curing Methods 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000006482 condensation reaction Methods 0.000 description 16
- 230000035699 permeability Effects 0.000 description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- 239000013522 chelant Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 7
- 229910001873 dinitrogen Inorganic materials 0.000 description 7
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 7
- 125000005372 silanol group Chemical group 0.000 description 7
- 239000010936 titanium Substances 0.000 description 7
- 229910052719 titanium Inorganic materials 0.000 description 7
- 239000007809 chemical reaction catalyst Substances 0.000 description 6
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin 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
- 239000012298 atmosphere Substances 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
- 238000010438 heat treatment Methods 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-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
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- 229920002379 silicone rubber Polymers 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000012855 volatile organic compound Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000000068 chlorophenyl group Chemical group 0.000 description 3
- 230000005494 condensation Effects 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
- 239000004615 ingredient Substances 0.000 description 3
- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 239000004945 silicone rubber Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000003944 tolyl group Chemical group 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
- 125000005023 xylyl group Chemical group 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
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-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
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000003863 ammonium salts Chemical class 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
- 229910052728 basic metal Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000013461 design Methods 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
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 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
- 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
- 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
- 230000001681 protective effect Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 150000003606 tin compounds Chemical class 0.000 description 2
- 150000003609 titanium compounds Chemical class 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- VBSTXRUAXCTZBQ-UHFFFAOYSA-N 1-hexyl-4-phenylpiperazine Chemical compound C1CN(CCCCCC)CCN1C1=CC=CC=C1 VBSTXRUAXCTZBQ-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- HTHNTJCVPNKCPZ-UHFFFAOYSA-N 2-chloro-1,1-difluoroethene Chemical group FC(F)=CCl HTHNTJCVPNKCPZ-UHFFFAOYSA-N 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- KTXWGMUMDPYXNN-UHFFFAOYSA-N 2-ethylhexan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-] KTXWGMUMDPYXNN-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
- ZYAASQNKCWTPKI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-amine Chemical compound CO[Si](C)(OC)CCCN ZYAASQNKCWTPKI-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
- TUXYZHVUPGXXQG-UHFFFAOYSA-M 4-bromobenzoate Chemical compound [O-]C(=O)C1=CC=C(Br)C=C1 TUXYZHVUPGXXQG-UHFFFAOYSA-M 0.000 description 1
- KMQLIDDEQAJAGJ-UHFFFAOYSA-N 4-oxo-4-phenylbutyric acid Chemical compound OC(=O)CCC(=O)C1=CC=CC=C1 KMQLIDDEQAJAGJ-UHFFFAOYSA-N 0.000 description 1
- LDNHMLRKFLFPIV-UHFFFAOYSA-N 4-trimethylsilyloxybutan-1-amine Chemical compound C[Si](C)(C)OCCCCN LDNHMLRKFLFPIV-UHFFFAOYSA-N 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
- USIBNHFIFAODEN-UHFFFAOYSA-N CC(=C)[Si](C)(C(=C)C)C(=C)C Chemical compound CC(=C)[Si](C)(C(=C)C)C(=C)C USIBNHFIFAODEN-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
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- JACRWUWPXAESPB-QMMMGPOBSA-N Tropic acid Natural products OC[C@H](C(O)=O)C1=CC=CC=C1 JACRWUWPXAESPB-QMMMGPOBSA-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
- 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
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical group CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 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
- 239000000853 adhesive Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005336 allyloxy 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
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 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
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 150000001805 chlorine compounds 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
- 239000011247 coating layer Substances 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-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 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
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- WPCPXPTZTOMGRF-UHFFFAOYSA-K di(butanoyloxy)alumanyl butanoate Chemical compound [Al+3].CCCC([O-])=O.CCCC([O-])=O.CCCC([O-])=O WPCPXPTZTOMGRF-UHFFFAOYSA-K 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 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
- 150000002009 diols Chemical class 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
- 238000010292 electrical insulation Methods 0.000 description 1
- 238000005530 etching 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
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 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
- 239000012847 fine chemical Substances 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
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 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
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 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
- 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
- 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- QIOYHIUHPGORLS-UHFFFAOYSA-N n,n-dimethyl-3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN(C)C QIOYHIUHPGORLS-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
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical group CCC(C)=NO WHIVNJATOVLWBW-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
- 125000001624 naphthyl 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
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 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
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- UOURRHZRLGCVDA-UHFFFAOYSA-D pentazinc;dicarbonate;hexahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Zn+2].[Zn+2].[Zn+2].[Zn+2].[Zn+2].[O-]C([O-])=O.[O-]C([O-])=O UOURRHZRLGCVDA-UHFFFAOYSA-D 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
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 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
- 238000007747 plating Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 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
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 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
- 229920005573 silicon-containing polymer Polymers 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
- 239000000126 substance 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
- 239000004408 titanium dioxide Substances 0.000 description 1
- 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 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
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 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
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 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 invention provides an organosilicon coating agent composition which does not contain organic solvent, has excellent storage stability, can be quickly cured at normal temperature after being coated on a substrate, can form a cured coating film with excellent transparency, adhesiveness and the like and excellent following performance to the bending of the substrate, and can provideThe corrosion resistance of the substrate is high, and particularly, the formation of sulfides by hydrogen sulfide as a sulfur-containing gas can be reduced. An organosilicon coating composition comprising: (A) an organotrisiloxane compound containing a hydrolyzable group represented by the following formula (1): 100 parts by mass of a water-soluble polymer,
(R1、R3is an unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, R2Is unsubstituted, halogen-substituted or alkyl-substituted phenyl, X is a hydrolyzable group selected from unsubstituted or alkoxy-substituted alkoxy, aryloxy, alkenyloxy, acyloxy and ketoxime groups, and a is 0 or 1. ) (B) 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 agent composition and the like that is crosslinked and cured at room temperature (23 ℃ ± 15 ℃) by hydrolysis-condensation reaction using moisture (moisture) in the atmosphere, and particularly relates to a silicone coating agent composition and the like used for electric and electronic components, structural material components and the like. The silicone coating agent composition of the present invention has excellent storage stability, can be cured quickly at room temperature after being applied to various substrates, and can provide a cured coating film having excellent transparency, flexibility (following properties to substrate bending), adhesion (adhesiveness to substrate), low gas permeability, and the like, and therefore can provide various functional characteristics such as surface protection, water repellency, rust prevention, water resistance, weather resistance, chemical resistance, stain resistance, and the like to various substrates.
Background
Silicone resins (organopolysiloxane resins) are different from other hydrocarbon-based organic resins in that they are excellent in heat resistance, weather resistance, water resistance, flame retardancy, and the like, and can form cured films having a surface with high hardness, and therefore curable silicone rubber compositions (silicone elastomer compositions) and silicone resin-based resins (polyorganosilsesquioxane resins having a three-dimensional network structure, and the like) having crosslinkable groups such as alkoxy groups and silanol groups bonded to silicon atoms in the molecule have been widely used in applications and fields such as surface protective materials for various substrates, heat-resistant coatings, weather-resistant coatings, water repellents, and various adhesives. Among them, silicone resins are used for conformal coatings of electronic substrates such as home electric appliances and electronic components because they are excellent in heat resistance and electrical insulation. Further, by designing the resin composition, a coating composition which does not require dilution of an organic solvent is also possible, and a coating agent which is excellent in VOC (volatile organic compound) problem and safety has been on the market. However, general silicone rubber-based or silicone resin-based coating agent compositions are expected to have a low protective effect against corrosive gases such as hydrogen sulfide and electrode metals (particularly silver electrodes), and thus are desired to be solved.
Heretofore, in order to reduce metal corrosion caused by corrosive gas such as hydrogen sulfide, acrylic resin-based or urethane resin-based coating agents have to be used, but such organic resin coating materials are generally used in a state diluted with an organic solvent, and have problems of VOC and safety. In addition, the range of use of acrylic and urethane coating agents is limited due to problems of heat resistance and electrical characteristics.
From the above, a solvent-free silicone-based coating agent having excellent ability to prevent metal corrosion by a corrosive gas such as hydrogen sulfide in addition to heat resistance and electrical characteristics has been desired.
The present invention is a material of a type which forms a hard coating after curing in a silicone coating agent, but as such a silicone coating agent composition, a so-called silicone varnish solution obtained by dissolving a curable silicone resin having a terminal silanol group and an average molecular weight of about 3000 to 2000000 in an organic solvent such as toluene or xylene has been used in many cases. When used, a coating film having excellent surface hardness, adhesion, heat resistance, weather resistance, water resistance and the like can be obtained, but since an organic solvent is used as an essential component and a dehydration condensation crosslinking reaction between silanol groups is utilized, generally, heat curing at 150 ℃ or higher for a long time is required for the formation of a coating film.
On the other hand, a one-pack type (one-pack type) solventless normal temperature curable silicone coating composition which does not contain an organic solvent, can be cured at normal temperature and has excellent storage stability is required, and studies on the use of a low molecular weight organosilane oxy oligomer obtained by partial (co) hydrolytic condensation of an organoalkoxysilane and on a curing catalyst which effectively promotes a hydrolysis reaction and a dealcoholization condensation reaction by moisture of the organosilane oxy oligomer to form a crosslinked coating film having a siloxane bond have been actively conducted, and techniques of cited documents have been proposed (patent documents 1 and 2: Japanese patent application laid-open No. 60-233164 and Japanese patent application laid-open No. 4110402).
However, in all of the techniques, the cured film obtained is poor in stiffness and flexibility, so that it has poor conformability to bending of the base material, and it is impossible to prevent metal corrosion due to hydrogen sulfide.
On the other hand, in the solvent-free silicone composition, as an example of a technique for preventing corrosion of a base metal by a sulfur-containing corrosive gas, there is a technique of adding a metal powder of silver, copper or the like to the composition to reduce corrosion of the base metal by sacrificial corrosion of the metal powder (patent documents 3 and 4: Japanese patent No. 4114037 and Japanese patent No. 4530137); a technique for reducing corrosion of a base metal by using an organic additive (patent document 5: Japanese patent No. 6418115). These techniques are excellent, but the effect is not sufficient depending on the type of corrosive gas as a means for detoxifying the corrosive gas species penetrating into the silicone coating film by the reaction inside the coating film.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 60-233164
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-mentioned drawbacks, and an object of the present invention is to provide an organosilicon coating agent composition which does not contain an organic solvent, does not impair the original characteristics of a curable organosilicon compound, has excellent storage stability as a coating agent composition, is rapidly cured at room temperature after being applied to a substrate, can form a cured coating film having excellent transparency, adhesion, and the like, and excellent conformability (flexibility) to bending of the substrate, and has low gas permeability, so that the corrosion resistance of the substrate can be improved, and particularly the formation of sulfides due to hydrogen sulfide as a sulfur-containing gas (a sulfur-containing gas) can be reduced.
Means for solving the problems
The present inventors have conducted intensive studies to achieve the above object, and as a result, have found that: the present inventors have found that a cured coating film having excellent transparency, adhesion, and the like, and excellent conformability (flexibility) to bending of a substrate can be provided by using a condensation reaction-curable silicone coating agent composition containing a curing catalyst and an organotrisiloxane compound represented by the following general formula (1) and having a specific molecular structure in which at least 1 unsubstituted or substituted phenyl group is contained in the molecule and at least 4, preferably 4 to 6 hydrolyzable groups are contained in the molecule as a main component, and that the cured coating film composition exhibits excellent storage stability under sealed conditions, is rapidly cured by a hydrolysis condensation reaction caused by moisture in the atmosphere in an open atmosphere, and has low gas permeability, so that the cured coating film can reduce the formation of sulfides due to hydrogen sulfide, and have completed the present invention.
Namely, the present invention provides the following silicone coating agent composition and an article sealed, coated, fixed or adhered with a cured product of the composition.
[1] An organosilicon coating composition comprising:
(A) an organotrisiloxane compound containing a hydrolyzable group represented by the following general formula (1): 100 parts by mass of a water-soluble polymer,
[ CHEM 1]
(in the formula, R1、R3Each independently is an unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, R2Is unsubstituted, halogen-substituted or alkyl-substituted phenyl, each X is independently at least one hydrolyzable group selected from unsubstituted or alkoxy-substituted alkoxy, aryloxy, alkenyloxy, acyloxy and ketoximino groups, and a is independently 0 or 1 for each bonded silicon atom. )
(B) Curing catalyst: 0.01 to 10 parts by mass.
[2][1]The silicone coating agent composition, wherein, in the general formula (1), R3Is unsubstituted, halogen substituted or alkyl substituted phenyl.
[3] [1] the silicone coating agent composition according to [1] or [2], wherein, in the general formula (1), X is a methoxy group, an ethoxy group, an isopropenyloxy group, or a ketoxime group.
[4] The silicone coating agent 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) and/or a partial hydrolysis condensate thereof (C) excluding the component (A) per 100 parts by mass of the component (A).
(R1)aSi(X)(4-a) (2)
(in the formula, R1X, a are each as described above. )
[5] The silicone coating agent composition according to any one of [1] to [4], which does not contain an organic solvent.
[6] The silicone coating agent composition according to any one of [1] to [5], wherein the 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)
(in the formula, R1X, a are each as described above. )
[ CHEM 2]
(in the formula, R2、R3Respectively, as described above. )
[7] An article sealed, coated, fixed or adhered with a cured product of the silicone coating agent composition according to any one of [1] to [6 ].
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, there is obtained an organosilicon coating agent composition which is excellent in storage stability, can be applied to a substrate even without containing an organic solvent, can form a cured coating rapidly at room temperature after application, is excellent in transparency, adhesion and the like, can obtain a cured coating excellent in followability (flexibility) to substrate bending, and is low in gas permeability, thereby improving corrosion resistance of the substrate and particularly reducing sulfide formation (sulfiting) by hydrogen sulfide which is a sulfur-containing gas.
Detailed Description
The present invention will be described in detail below.
[ (A) component ]
(A) Component (b) is a main component of the silicone coating agent composition of the present invention, and is an organotrisiloxane compound represented by the following general formula (1) having a specific molecular structure in which at least 1 unsubstituted or substituted phenyl group is present in the molecule and at least 4, preferably 4 to 6 hydrolyzable groups are present in the molecule.
(A) The hydrolyzable group-containing organotrisiloxane compound of component (a) is rapidly crosslinked and cured by hydrolysis-condensation reaction due to moisture (moisture) in the atmosphere at room temperature (23 ℃ ± 15 ℃, the same applies) in the presence of a curing catalyst of component (B) described later, and a cured coating film having excellent transparency, adhesion, and the like, excellent conformability (flexibility) to bending of a substrate, and suppressed gas permeability can be formed.
[ CHEM 3]
(in the formula, R1、R3Each independently is an unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, R2Is unsubstituted, halogen-substituted or alkyl-substituted phenyl, each X is independently at least one hydrolyzable group selected from unsubstituted or alkoxy-substituted alkoxy, aryloxy, alkenyloxy, acyloxy and ketoximino groups, and a is independently 0 or 1 for each bonded silicon atom. )
In the above formula (1), R1、R3Each independently an unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, and examples thereof include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, neopentyl, hexyl, cyclohexyl, heptyl, octyl, 2-ethylhexyl, nonyl and decylLinear, branched or cyclic alkyl group having 1 to 10 carbon atoms, vinyl group, allyl group, propenyl group, isopropenyl group, butenyl group, isobutenyl group, pentenyl group, hexenyl group, cyclohexenyl group and the like, linear, branched or cyclic alkenyl group having 2 to 10 carbon atoms, phenyl group, tolyl group, xylyl group, naphthyl group and the like, aryl group having 6 to 10 carbon atoms, mesityl group and the like, aralkyl group having 7 to 10 carbon atoms, benzyl group, phenylethyl group and the like, chloromethyl group, 2-bromoethyl group, 3, 3, 3-trifluoropropyl group, 3, 3, 4, 4, 5, 5, 5-heptafluoropentyl group, 2, 3, 3-trifluoro-2-chlorocyclobutyl group, 3, 4-dibromo-1-chlorohexyl group, 3, 3, 3, 4, 4, 5, 5-chlorohexyl group and the like, which are substituted with a halogen atom or the like, A halogen-substituted monovalent hydrocarbon group such as difluoromonochloroethylene, 2-iodocyclohexenyl, chlorophenyl, perchlorophenyl, fluorophenyl, perfluorophenyl, 2, 2, 2-trifluoromethylphenyl, 2, 4-dibromobenzyl.
Among these, as R1Methyl, ethyl, propyl, vinyl, phenyl and, as in the case of R described later, R is preferred2As described in the section (a) above, when low gas permeability of the cured film to be obtained is important, it is preferable that the cured film be an unsubstituted, halogen-substituted or alkyl-substituted phenyl group, and various other monovalent organic groups can be selected for the design of the curing rate by the hydrolysis-condensation reaction of the composition of the present invention.
As R3From the viewpoint of reducing the gas permeability of the cured film obtained, an unsubstituted, halogen-substituted or alkyl-substituted phenyl group such as a phenyl group, tolyl group, xylyl group, chlorophenyl group, all-chlorophenyl group, fluorophenyl group, perfluorophenyl group, 2, 2, 2-trifluoromethylphenyl group, or the like is preferable.
In addition, as R3By using a monovalent hydrocarbon group other than the above unsubstituted, halogen-substituted or alkyl-substituted phenyl group, the Tg of the cured coating film can be controlled, and the cured coating film can have a low gas permeability and a low Tg to R3Various designs were made. Among these, alkyl groups, allyl groups, and fluoroalkyl groups are particularly preferable because the cured film obtained has good releasability and water repellency.
In the above formula (1), R2The organotrisiloxane compound represented by formula (1) of 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, all-chlorophenyl group, fluorophenyl group, perfluorophenyl group, 2, 2, 2-trifluoromethylphenyl group, etc.). When importance is attached to low gas permeability, it is preferable to have 2 (i.e., R) in the molecule2And R3Both) unsubstituted, halogen-substituted or alkyl-substituted phenyl.
The gas permeability of the cured coating is reduced by the unsubstituted or substituted phenyl group, and the gas permeability of the cured coating is increased for the organotrisiloxane compound having no unsubstituted or substituted phenyl group in the molecule, and corrosion of the base metal by the corrosive gas can no longer be reduced.
In the formula (1), each X is independently at least one hydrolyzable group selected from unsubstituted or alkoxy-substituted alkoxy, aryloxy, alkenyloxy, acyloxy and ketoxime groups. Specific examples of X include a hydrolyzable group of at least one member selected from the group consisting of C1-7 unsubstituted or alkoxy-substituted alkoxy, aryloxy, alkenyloxy, acyloxy and ketoximino groups, and examples thereof include C1-6 alkoxy groups such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy and tert-butoxy groups, C2-4 alkoxy groups such as C1-4 alkoxy, methoxy-substituted methoxy, methoxy-substituted ethoxy, ethoxy-substituted methoxy and ethoxy-substituted ethoxy groups, C2-4 alkenyloxy groups such as vinyloxy, allyloxy, propenyloxy, isopropenyloxy and butenyloxy groups, C6-10 aryloxy groups such as phenoxy groups, C6-10 aryloxy groups such as acetoxy and propionyloxy groups, C2-4 acyloxy groups such as acetoxy and propionyloxy groups, and the like, And ketoxime groups having 3 to 6 carbon atoms such as a dimethyl ketoxime group, a methyl ethyl ketoxime group, and a diethyl ketoxime group. Preferred are methoxy, ethoxy, isopropenyloxy, methylethylketoximino and the like.
a is independently 0 or 1, preferably 1, for each bonded silicon atom.
(A) The hydrolyzable group-containing organotrisiloxane compound of component (1) has at least 4, preferably 4 to 6, and more preferably 4 hydrolyzable groups X in 1 molecule, and an appropriate leaving group can be selected in order to achieve desired curing speed and storage property characteristics.
As the hydrolyzable group-containing organotrisiloxane compound represented by formula (1), the following compounds can be specifically exemplified.
[ CHEM 4]
[ CHEM 5]
Further, the above-mentioned R having a 1-valent hydrocarbon group bonded to a silicon atom represented by the following general formula (2) is reacted in the presence of a condensation reaction catalyst under conventionally known conditions1And a hydrolyzable group X, and a hydrolyzable organosilane compound represented by the following general formula (3) each having 1 of the above-mentioned R2And R3The hydrolyzable group-containing organotrisiloxane compound represented by the above general formula (1) of component (a) can be easily produced by subjecting a diorganosilanediol (diorganodihydroxysilane) having at least 1, preferably 2 unsubstituted, halogen-substituted or alkyl-substituted phenyl groups in the molecule, which is a 1-valent hydrocarbon group bonded to a silicon atom, to a hydrolysis-condensation reaction.
(R1)aSi(X)(4-a) (2)
[ CHEM 6]
(in the formulae, R1、R2、R3X, a are each as described above. )
Specific examples of the hydrolyzable organosilane compound represented by the formula (2) include vinyltrimethoxysilane, phenyltrimethoxysilane, methyltrimethoxysilane, vinyltriethoxysilane, phenyltriethoxysilane, methyltriethoxysilane, vinyltriisopropenoxysilane, phenyltriisopropenoxysilane, and methyltriisopropenylsilane.
Specific examples of the diorganosilanediol represented by the formula (3) include diphenylsilanediol, methylphenylsilanediol, and ethylphenylsilanediol.
The reaction ratio of the hydrolyzable organosilane compound represented by the formula (2) to the diorganosilanediol 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 diorganosilanediol 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 the number of remaining 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 5 mol or less. When many 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 silane compound containing a guanidine group 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 may be an amount sufficient to allow the condensation reaction between the diorganosilanediol represented by the formula (3) and the hydrolyzable organosilane compound represented by the formula (2) to proceed at room temperature to under heating, and is usually preferably 0.01 to 10 parts by mass, particularly preferably about 0.1 to 5 parts by mass, based on 100 parts by mass of the total of the diorganosilanediol and the hydrolyzable organosilane compound.
The reaction conditions are preferably about 0 to 150 ℃, particularly about 25 to 100 ℃, and about 5 to 120 minutes, particularly about 10 to 60 minutes, and the reaction product (component (A)) can be obtained by reacting the alcohol and the like by-produced by the condensation reaction while removing it.
In the silicone coating agent composition of the present invention, the hydrolyzable group-containing organotrisiloxane compound of component (a) can be used alone in 1 kind, or in combination of 2 or more kinds.
[ (B) component ]
(B) The curing catalyst of component (a) is a condensation reaction catalyst required for the composition of the present invention to rapidly form a cured coating film by hydrolysis-condensation reaction of the hydrolyzable group-containing organotrisiloxane compound of component (a) represented by general formula (1) with moisture (moisture) in the atmosphere in the curing step, and is selected from the group consisting of an organotin compound, an organoaluminum compound, an organotitanium compound, an organozirconium compound, and an organic base compound, and an appropriate catalyst is selected depending on the reactivity of the hydrolyzable group X selected in general formula (1) of component (a).
Examples of such a condensation reaction catalyst include hydroxides, oxides, or basic metal salts of alkali metals or 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, basic metal salts such as basic zinc carbonate and basic magnesium carbonate can be exemplified.
In addition, as other condensation reaction catalysts, aluminum chelate compounds, organic titanium compounds, organic tin compounds, aminoalkylalkoxysilanes, ammonium salts, and the like can also be used. Examples of the aluminum chelate compound include ethyl acetoacetate diisopropoxyaluminum, tris (ethyl acetate) aluminum, tris (acetylacetonato (アルミニウムトリス (エチルアセテート)) aluminum, bis (ethyl acetoacetate) monoacetylacetonato aluminum, and examples of the organic titanium compound include tetraisopropoxytitanium, tetra-n-butoxytitanium, tetrakis (2-ethylhexyloxy) titanium, and examples of the organic tin compound include dibutyltin diacetate, dibutyltin dilaurate, dibutyltin dioctoate, stannous octoate, stannous naphthenate, stannous oleate, stannous isobutyrate, stannous linoleate, stannous stearate, stannous benzoate, stannous naphthoate, stannous laurate, stannous o-thymite, stannous β -benzoylpropionate, stannous crotonate, stannous tropic acid, stannous p-bromobenzoate, stannous palmitoleate, stannous palmitate, and the like, Tin salts of carboxylic acids such as stannous cinnamate and stannous phenylacetate. Examples of aminoalkylalkoxysilanes include γ -aminopropyltrimethylmethoxysilane, γ -aminopropyltriethoxysilane, N- (. beta. -aminoethyl) - γ -aminopropyltrimethoxysilane, γ -aminopropylmethyldimethoxysilane, N- (. beta. -aminoethyl) - γ -aminopropylmethyldimethoxysilane and γ - (dimethylamino) propyltrimethoxysilane. Examples of the ammonium salt include salts of acids and amines, examples of the acids include acetic acid and formic acid, and examples of the amines include allylamine, 2-ethylhexylamine, 3-ethoxypropylamine, diisobutylamine, 3-diethylaminopropylamine, di-2-ethylhexylamine, dibutylaminopropylamine, tri-n-octylamine, tert-butylamine, sec-butylamine, propylamine, and 3-methoxypropylamine.
The amount of the curing catalyst of 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 component (a), from the viewpoint that the reaction proceeds well and the curability of the obtained silicone coating agent composition becomes good.
[ (C) ingredient ]
The silicone coating agent composition of the present invention may further contain a hydrolyzable organosilane compound (C) represented by the above formula (2) which is the same as the component used for producing the above component (a), in addition to the above component (a) and component (B). When the component (C) is blended, the effect of improving the storage stability of the composition and controlling the curing time (pot life) of the composition can be obtained.
When the hydrolyzable silane compound represented by the above formula (2) is reacted with the diorganosilane diol represented by the above formula (3) to obtain the component (a), the hydrolyzable silane compound represented by the above formula (2) is reacted in excess, and the remaining hydrolyzable silane compound represented by the above 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, relative to 100 parts by mass of the component (a).
[ other ingredients ]
The silicone coating agent composition of the present invention may further contain, if necessary, a small amount of various additives, for example, a plasticizer, a release agent, a flame retardant, an antioxidant, an ultraviolet absorber, a pigment such as titanium dioxide, carbon black, or iron oxide, and a dye, in a range not to impair the object of the present invention. Similarly, fillers such as fumed silica, silica aerosol, silica gel, reinforcing silica fillers treated with organosilanes, organosiloxanes, or organosilazanes, asbestos, ground fused silica, alumina, aluminum silicate, zirconium silicate, magnesium oxide, zinc oxide, talc, diatomaceous earth, mica, calcium carbonate, clay, zirconia, 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 as long as the object of the present invention is not impaired.
Further, an organic solvent may be added as needed, and it is preferable that the composition contains no organic solvent or contains a small amount of organic solvent from the viewpoint of VOC and safety as long as the composition has a viscosity usable in the process.
In the production of the silicone coating agent composition of the present invention, the prescribed amounts of the above-mentioned components (a) and (B) may be simply mixed, and in this case, the temperature at the time of mixing is not limited, and in particular, the mixing can be easily achieved by stirring and mixing at room temperature for 10 minutes or more, 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 a cured product of the composition.
The silicone coating agent composition of the present invention can be applied and cured to various metal substrates, wood, stone, plasterboard, slate, tile, concrete, glass, ceramics, plastic products, organic resin coated products, and the like by a conventionally known method to form a coating film. In this case, as a coating method, specifically, methods such as brush coating, spray coating, dipping, flow coater, blade coater, spin coater, and the like can be cited, and further, on-site coating can be performed. The coating amount varies depending on the type of the substrate and the purpose of coating, and may be generally in the range of 0.1 to 200 μm, preferably 1 to 100 μm, in thickness of the coating after curing.
The curing conditions of the silicone coating agent composition of the present invention are not particularly limited, and since the coating film is formed by curing with moisture in the air, the coating film can be dried (tack-free state) by leaving the coating film at a temperature ranging from room temperature to 80 ℃ for about 1 minute to 2 hours, and the curing reaction can be completed by leaving the coating film 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 a cured product of the composition.
Examples
The present invention will be described in more detail below by way of examples, which are not intended to limit the scope of the present invention. In each example, room temperature means 25 ℃ and viscosity means a measurement value obtained by a rotational viscometer at 25 ℃.
[ preparation examples ]
(A) Composition (I)
(A-1)
Diphenylsilanediol (16.2g), vinyltrimethoxysilane (25g) and a titanium chelate catalyst (0.2g, produced by Matsumoto Fine Chemical Co. Ltd., ORGATIX TC-401) were added to a 100ml flask, and after a reaction at 100 ℃ for 60 minutes, the produced methanol and the remaining vinyltrimethoxysilane were removed by flowing nitrogen gas, thereby obtaining an organotrisiloxane compound (A-1) represented by the following formula.
[ CHEM 7]
(A-2)
Diphenylsilanediol (16.2g), phenyltrimethoxysilane (25g) and a titanium chelate catalyst (0.2g, produced by Matsumoto Fine Chemical Co. Ltd., ORGATIX TC-401) were added to a 100ml flask, and after a reaction at 100 ℃ for 60 minutes, the generated methanol was removed by flowing nitrogen gas, and then the remaining phenyltrimethoxysilane was removed by heating under reduced pressure, thereby obtaining an organotrisiloxane compound (A-2) represented by the following formula.
[ CHEM 8 ]
(A-3)
Diphenylsilanediol (16.2g), methyltrimethoxysilane (25g), and a titanium chelate catalyst (0.2g, produced by Matsumoto Fine Chemical Co. Ltd., ORGATIX TC-401) were added to a 100ml flask, and after allowing to react at 100 ℃ for 60 minutes, the produced methanol and the remaining methyltrimethoxysilane were removed by flowing nitrogen gas, thereby obtaining an organotrisiloxane compound (A-3) represented by the following formula.
[ CHEM 9 ]
(A-4)
Diphenylsilanediol (16.2g), vinyltriisopropenoxysilane (25g), and tetramethylguanidinopropyltrimethoxysilane (0.2g) were added to a 100ml flask, and after 60 minutes of reaction at 100 ℃, the acetone produced was removed by flowing nitrogen gas, and then the remaining vinyltriisopropenoxysilane was removed by heating under reduced pressure to obtain an organotrisiloxane compound (a-4) represented by the following formula.
[ CHEM 10 ]
(A-5)
Methylphenylsilane diol (16.2g, partially dimerized), vinyltrimethoxysilane (25g), and a titanium chelate catalyst (0.2g, manufactured by Matsumoto Fine Chemical Co. Ltd., ORGATIX TC-401) were added to a 100ml flask, and after 60 minutes of reaction at 100 ℃, the generated methanol and the remaining vinyltrimethoxysilane were removed by flowing nitrogen gas, thereby obtaining an organotrisiloxane compound (A-5) represented by the following formula.
[ CHEM 11 ]
(A) Ingredients (for comparison)
(a-1)
Dimethylsilanediol (12.3g, partially dimerized), methyltrimethoxysilane (20g), and a titanium chelate catalyst (0.2g, produced by Matsumoto Fine Chemical Co. Ltd., ORGATIX TC-401) were added to a 100ml flask, and after 60 minutes of reaction at 100 ℃, the produced methanol and the remaining methyltrimethoxysilane were removed by flowing nitrogen gas, thereby obtaining an organotrisiloxane compound (a-1) represented by the following formula.
[ CHEM 12 ]
(a-2)
In a 100ml flask, a hydroxyl-terminated dimethyl silicone polymer (700mpa.s, 300g), methyltrimethoxysilane (25g), and a titanium chelate catalyst (0.2g, produced by Matsumoto Fine Chemical co.ltd., ORGATIX TC-401) were added, and after 60 minutes of reaction at 100 ℃, the generated methanol was removed by flowing nitrogen gas, and then the remaining methyltrimethoxysilane was removed by heating under reduced pressure, thereby obtaining an organopolysiloxane compound (a-2) represented by the following formula.
[ CHEM 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 a 10ml glass cup in respective amounts, and manually mixed, and stirred at room temperature for 10 minutes to obtain an organosilicon coating agent composition. The components (A-1) to (A-5), (a-1) and (a-2) are solvent-free. The appearance and properties of the obtained silicone coating agent composition were visually confirmed and are also 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 resulting cured product were visually confirmed and are shown in tables 1 and 2.
The raw materials used in addition to the component (a) obtained in the above preparation examples are shown below.
(B) Composition (I)
(B-1)
Tin catalyst: u-830 (manufactured by Ridonghua Kabushiki Kaisha, dioctyltin)
(B-2)
Amine catalyst: tetramethyl guanidinopropyltrimethoxysilane
(C) Composition (I)
(C-1)
Vinyl trimethoxy silane
(A) Composition (I)(for comparison)
(a-3)
A solvent-based coating agent mainly containing an acrylic resin component was prepared: humiseal (registered trademark) -1B66 NS. The solid content was 35% by mass (solvent content 65% by mass), and the film was coated by diluting the film twice with an additional solvent (dilution material Humiseal (registered trademark) シンナー 901).
[ TABLE 1]
[ TABLE 2]
Next, the silicone coating agent compositions of the examples and comparative example 3 using the component (a-3) were used to evaluate the appearance, tack-free time, corrosion resistance test and flexibility of the cured product. The results are shown in Table 3.
(appearance of cured product)
The coating cured on the aluminum dish, which was produced in the evaluation of the tack-free time described below, was evaluated for transparency and degree of coloration by visual observation.
(tack free time)
0.20g of each composition (liquid) was collected on an aluminum dish and applied to a thickness of 2 cm. times.2 cm (4 cm)2) The square of (2) was evaluated by setting the time until the adhesive property of the surface of each composition was lost by touching with a finger as the curing time (tack free time).
(test for Corrosion resistance)
Each material (silicone coating agent composition) was coated on the surface of a silver-plated aluminum plate at 0.08g of each composition (liquid) to 2 cm. times.2 cm (4 cm) so that the cured coating film became about 200. mu.m2) The square of (2) was cured under curing conditions of 23 ℃/50% Rh X7 days, and a hydrogen sulfide gas corrosion tester was used for the curing over time (initial phase, time, and time,1 day later, 3 days later, 7 days later, 14 days later) of the silver plating surface. The etching conditions are as follows.
Concentration of hydrogen sulfide: 2ppm of
Temperature: 23 deg.C
Humidity: 50% Rh
The silver-plated surfaces before and after the corrosion test were observed, and it was judged that the corrosion had occurred at the time of the initial change in silver gloss (blackening, graying).
(flexibility)
When the silver-plated aluminum plate coated (having the cured coating film of the silicone coating agent composition) after the completion of the corrosion resistance test was bent, it was evaluated whether the coating layer could follow the substrate without cracking.
[ TABLE 3]
(results)
From the above results, it was confirmed that: the silicone coating agent composition of the present invention is excellent in curability and transparency at room temperature, and is excellent in the effect of preventing corrosion of a metal base material by a corrosive gas and in the ability to follow the base material (flexibility).
Claims (7)
1. An organosilicon coating composition comprising:
(A) an organotrisiloxane compound containing a hydrolyzable group represented by the following general formula (1): 100 parts by mass of a water-soluble polymer,
[ CHEM 1]
In the formula, R1、R3Each independently is an unsubstituted or halogen-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, R2Is unsubstituted, halogen-substituted or alkyl-substituted phenyl, X is independently selected from unsubstituted or alkoxy-substituted alkoxy, aryloxy, alkenyloxy,A is 0 or 1 independently for each bonded silicon atom,
(B) curing catalyst: 0.01 to 10 parts by mass.
2. The silicone coating agent composition according to claim 1, wherein, in the general formula (1), R3Is unsubstituted, halogen substituted or alkyl substituted phenyl.
3. The silicone coating agent composition according to claim 1 or 2, wherein, in the general formula (1), X is a methoxy group, an ethoxy group, an isopropenyloxy group, or a ketoxime group.
4. The silicone coating agent 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) and/or a partial hydrolysis condensate thereof (C) excluding component (A) with respect to 100 parts by mass of component (A),
(R1)aSi(X)(4-a) (2)
in the formula, R1X, a are each as described above.
5. The silicone coating agent composition according to claim 1 or 2, which is free of an organic solvent.
6. The silicone coating agent composition according to claim 1 or 2, wherein component (a) is a hydrolysis-condensation reactant 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)
in the formula, R1X, a are each the same as described above,
[ CHEM 2]
In the formula, R2、R3Respectively, as described above.
7. An article sealed, coated, fixed or adhered with a cured product of the silicone coating agent composition according to any one of claims 1 to 6.
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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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