CN102732151A - 拒油涂布材料组合物 - Google Patents
拒油涂布材料组合物 Download PDFInfo
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- CN102732151A CN102732151A CN2012101014638A CN201210101463A CN102732151A CN 102732151 A CN102732151 A CN 102732151A CN 2012101014638 A CN2012101014638 A CN 2012101014638A CN 201210101463 A CN201210101463 A CN 201210101463A CN 102732151 A CN102732151 A CN 102732151A
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- China
- Prior art keywords
- och
- coating material
- group
- sich
- alkyl
- Prior art date
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- 239000000463 material Substances 0.000 title claims abstract description 58
- 239000011248 coating agent Substances 0.000 title claims abstract description 49
- 238000000576 coating method Methods 0.000 title claims abstract description 49
- 239000005871 repellent Substances 0.000 title abstract description 25
- 239000000203 mixture Substances 0.000 title abstract description 20
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 28
- 238000009833 condensation Methods 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 230000005494 condensation Effects 0.000 claims abstract description 9
- 125000000962 organic group Chemical group 0.000 claims abstract description 7
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 6
- 125000006850 spacer group Chemical group 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 9
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 11
- 229920001971 elastomer Polymers 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000005060 rubber Substances 0.000 claims description 10
- 239000007859 condensation product Substances 0.000 claims description 8
- 229920002050 silicone resin Polymers 0.000 claims description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 abstract description 3
- 150000002430 hydrocarbons Chemical group 0.000 abstract description 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- -1 Methyl Chemical group 0.000 description 44
- 238000012360 testing method Methods 0.000 description 31
- 239000003921 oil Substances 0.000 description 28
- 238000002360 preparation method Methods 0.000 description 23
- 230000002940 repellent Effects 0.000 description 23
- 229910052751 metal Inorganic materials 0.000 description 17
- 239000002184 metal Substances 0.000 description 17
- 238000000034 method Methods 0.000 description 17
- 150000001721 carbon Chemical group 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 238000006482 condensation reaction Methods 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 229910000077 silane Inorganic materials 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229920000260 silastic Polymers 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 235000012239 silicon dioxide Nutrition 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- 150000004703 alkoxides Chemical class 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 125000005375 organosiloxane group Chemical group 0.000 description 4
- 229960001866 silicon dioxide Drugs 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 3
- 125000005370 alkoxysilyl group Chemical group 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 description 3
- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 3
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 3
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- ZZHNUBIHHLQNHX-UHFFFAOYSA-N butoxysilane Chemical class CCCCO[SiH3] ZZHNUBIHHLQNHX-UHFFFAOYSA-N 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical compound CCO[Si](C)OCC GAURFLBIDLSLQU-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- RBCYCMNKVQPXDR-UHFFFAOYSA-N phenoxysilane Chemical compound [SiH3]OC1=CC=CC=C1 RBCYCMNKVQPXDR-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- 239000004945 silicone rubber Substances 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- AUEJBKCWXPYRGZ-UHFFFAOYSA-N 1,1'-biphenyl diethoxysilane Chemical compound C(C)O[SiH2]OCC.C1(=CC=CC=C1)C1=CC=CC=C1 AUEJBKCWXPYRGZ-UHFFFAOYSA-N 0.000 description 1
- HUYPAUVBFFWHOQ-UHFFFAOYSA-N 1-[butyl(dimethyl)silyl]oxyethyl prop-2-enoate Chemical compound CCCC[Si](OC(C)OC(=O)C=C)(C)C HUYPAUVBFFWHOQ-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
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- DAJFVZRDKCROQC-UHFFFAOYSA-N 3-(oxiran-2-ylmethoxy)propyl-tripropoxysilane Chemical compound CCCO[Si](OCCC)(OCCC)CCCOCC1CO1 DAJFVZRDKCROQC-UHFFFAOYSA-N 0.000 description 1
- HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-UHFFFAOYSA-N 0.000 description 1
- DOYKFSOCSXVQAN-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CCO[Si](C)(OCC)CCCOC(=O)C(C)=C DOYKFSOCSXVQAN-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
- LZMNXXQIQIHFGC-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C(C)=C LZMNXXQIQIHFGC-UHFFFAOYSA-N 0.000 description 1
- KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 description 1
- KEZMLECYELSZDC-UHFFFAOYSA-N 3-chloropropyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(OCC)CCCCl KEZMLECYELSZDC-UHFFFAOYSA-N 0.000 description 1
- KNTKCYKJRSMRMZ-UHFFFAOYSA-N 3-chloropropyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CCCCl KNTKCYKJRSMRMZ-UHFFFAOYSA-N 0.000 description 1
- GBQYMXVQHATSCC-UHFFFAOYSA-N 3-triethoxysilylpropanenitrile Chemical compound CCO[Si](OCC)(OCC)CCC#N GBQYMXVQHATSCC-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- 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
- DDSBPUYZPWNNGH-UHFFFAOYSA-N 6-n-[(4-nitrophenyl)methyl]-2-n-[[3-(trifluoromethyl)phenyl]methyl]-7h-purine-2,6-diamine Chemical compound C1=CC([N+](=O)[O-])=CC=C1CNC1=NC(NCC=2C=C(C=CC=2)C(F)(F)F)=NC2=C1NC=N2 DDSBPUYZPWNNGH-UHFFFAOYSA-N 0.000 description 1
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- 239000005995 Aluminium silicate Substances 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
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- NJOPBCZQSPNWLW-UHFFFAOYSA-N C(C)O[SiH2]OCC.CC=C Chemical compound C(C)O[SiH2]OCC.CC=C NJOPBCZQSPNWLW-UHFFFAOYSA-N 0.000 description 1
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- PZDBZWREYGMSGP-UHFFFAOYSA-N C(C1CO1)OC(CC(C)O[Si](OCC)(OCC)CC)C Chemical compound C(C1CO1)OC(CC(C)O[Si](OCC)(OCC)CC)C PZDBZWREYGMSGP-UHFFFAOYSA-N 0.000 description 1
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- WIJPHQMSTAPTKQ-UHFFFAOYSA-N C(C1CO1)OC(CC)CO[Si](OC)(C)CC Chemical compound C(C1CO1)OC(CC)CO[Si](OC)(C)CC WIJPHQMSTAPTKQ-UHFFFAOYSA-N 0.000 description 1
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- MCKWYBMOGZCGFR-UHFFFAOYSA-N C(C1CO1)OCCCC(OOOC)C Chemical compound C(C1CO1)OCCCC(OOOC)C MCKWYBMOGZCGFR-UHFFFAOYSA-N 0.000 description 1
- URTMLMIDVJFZRG-UHFFFAOYSA-N CCCC[Si](OCC)(OCC)OCCC(CC)OCC1CO1 Chemical compound CCCC[Si](OCC)(OCC)OCCC(CC)OCC1CO1 URTMLMIDVJFZRG-UHFFFAOYSA-N 0.000 description 1
- RXVDXXYYJHSRQM-UHFFFAOYSA-N CCCC[Si](OCC)(OCC)OCCCC(C)OCC1CO1 Chemical compound CCCC[Si](OCC)(OCC)OCCCC(C)OCC1CO1 RXVDXXYYJHSRQM-UHFFFAOYSA-N 0.000 description 1
- XUMOCLKKNLPDTH-UHFFFAOYSA-N CCCC[Si](OCC)(OCC)OCCCCCOCC1CO1 Chemical compound CCCC[Si](OCC)(OCC)OCCCCCOCC1CO1 XUMOCLKKNLPDTH-UHFFFAOYSA-N 0.000 description 1
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- JACFXKQPAFJQLQ-UHFFFAOYSA-N CCNCC.CCO[SiH2]OCC Chemical compound CCNCC.CCO[SiH2]OCC JACFXKQPAFJQLQ-UHFFFAOYSA-N 0.000 description 1
- KAOLRQUUXBEACM-UHFFFAOYSA-N CCNCC.CO[SiH2]OC Chemical compound CCNCC.CO[SiH2]OC KAOLRQUUXBEACM-UHFFFAOYSA-N 0.000 description 1
- MVHZHMKEBJJTCH-UHFFFAOYSA-N CN(C)C.CO[SiH3] Chemical compound CN(C)C.CO[SiH3] MVHZHMKEBJJTCH-UHFFFAOYSA-N 0.000 description 1
- PXJZCBUXFVZSLL-UHFFFAOYSA-N CO[SiH2]OC.C=CC Chemical compound CO[SiH2]OC.C=CC PXJZCBUXFVZSLL-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- SUHOOTKUPISOBE-UHFFFAOYSA-N O-phosphoethanolamine Chemical compound NCCOP(O)(O)=O SUHOOTKUPISOBE-UHFFFAOYSA-N 0.000 description 1
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- FMFFCKHBRSQWFK-UHFFFAOYSA-N butyl-dimethoxy-[4-(oxiran-2-ylmethoxy)butoxy]silane Chemical compound C(CCC)[Si](OCCCCOCC1CO1)(OC)OC FMFFCKHBRSQWFK-UHFFFAOYSA-N 0.000 description 1
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- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
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- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
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- JWDQBQBPUSPIHZ-UHFFFAOYSA-N diethoxy-ethyl-[3-(oxiran-2-ylmethoxy)pentan-2-yloxy]silane Chemical compound C(C1CO1)OC(CC)C(C)O[Si](OCC)(OCC)CC JWDQBQBPUSPIHZ-UHFFFAOYSA-N 0.000 description 1
- ODADONMDNZJQMW-UHFFFAOYSA-N diethoxy-ethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](CC)(OCC)CCCOCC1CO1 ODADONMDNZJQMW-UHFFFAOYSA-N 0.000 description 1
- FTUJVDGSKMWKAN-UHFFFAOYSA-N diethoxy-methyl-[1-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)C(CC)OCC1CO1 FTUJVDGSKMWKAN-UHFFFAOYSA-N 0.000 description 1
- HUFWVNRUIVIGCH-UHFFFAOYSA-N diethoxy-methyl-[2-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CC(C)OCC1CO1 HUFWVNRUIVIGCH-UHFFFAOYSA-N 0.000 description 1
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 1
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- VDCSZEZNBODVRT-UHFFFAOYSA-N dimethoxy-[3-(oxiran-2-ylmethoxy)propyl]-phenylsilane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)CCCOCC1CO1 VDCSZEZNBODVRT-UHFFFAOYSA-N 0.000 description 1
- NFCHYERDRQUCGJ-UHFFFAOYSA-N dimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[SiH](OC)CCCOCC1CO1 NFCHYERDRQUCGJ-UHFFFAOYSA-N 0.000 description 1
- KQODNYDIZIFQGO-UHFFFAOYSA-N dimethoxy-methyl-[1-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)C(CC)OCC1CO1 KQODNYDIZIFQGO-UHFFFAOYSA-N 0.000 description 1
- SYPWIQUCQXCZCF-UHFFFAOYSA-N dimethoxy-methyl-[2-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CC(C)OCC1CO1 SYPWIQUCQXCZCF-UHFFFAOYSA-N 0.000 description 1
- UFXYMLGIRKSLGL-UHFFFAOYSA-N dimethoxy-methyl-[4-(oxiran-2-ylmethoxy)butoxy]silane Chemical compound C(C1CO1)OCCCCO[Si](OC)(OC)C UFXYMLGIRKSLGL-UHFFFAOYSA-N 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
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- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- VBEAJYZVNIOING-UHFFFAOYSA-N ethenyl-diethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C=C)(OCC)CCCOCC1CO1 VBEAJYZVNIOING-UHFFFAOYSA-N 0.000 description 1
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- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
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- KUCGHDUQOVVQED-UHFFFAOYSA-N ethyl(tripropoxy)silane Chemical compound CCCO[Si](CC)(OCCC)OCCC KUCGHDUQOVVQED-UHFFFAOYSA-N 0.000 description 1
- YCIAPTIZYCRWAU-UHFFFAOYSA-N ethyl-[3-(oxiran-2-ylmethoxy)propyl]-dipropoxysilane Chemical compound CCCO[Si](CC)(OCCC)CCCOCC1CO1 YCIAPTIZYCRWAU-UHFFFAOYSA-N 0.000 description 1
- GORAQHJKPKSEPK-UHFFFAOYSA-N ethyl-dimethoxy-[2-(oxiran-2-ylmethoxy)butoxy]silane Chemical compound C(C1CO1)OC(CC)CO[Si](OC)(OC)CC GORAQHJKPKSEPK-UHFFFAOYSA-N 0.000 description 1
- BHGXEXJPOQMRQY-UHFFFAOYSA-N ethyl-dimethoxy-[3-(oxiran-2-ylmethoxy)butoxy]silane Chemical compound C(C1CO1)OC(CCO[Si](OC)(OC)CC)C BHGXEXJPOQMRQY-UHFFFAOYSA-N 0.000 description 1
- YYDBOMXUCPLLSK-UHFFFAOYSA-N ethyl-dimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CC[Si](OC)(OC)CCCOCC1CO1 YYDBOMXUCPLLSK-UHFFFAOYSA-N 0.000 description 1
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- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
- 239000001095 magnesium carbonate 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
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 229960001708 magnesium carbonate Drugs 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
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- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000004704 methoxides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
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- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
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- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
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- 229910017604 nitric acid Inorganic materials 0.000 description 1
- RGHXWDVNBYKJQH-UHFFFAOYSA-N nitroacetic acid Chemical compound OC(=O)C[N+]([O-])=O RGHXWDVNBYKJQH-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000005474 octanoate group Chemical group 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 150000004812 organic fluorine compounds Chemical class 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000010702 perfluoropolyether Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- JTQPTNQXCUMDRK-UHFFFAOYSA-N propan-2-olate;titanium(2+) Chemical compound CC(C)O[Ti]OC(C)C JTQPTNQXCUMDRK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- AKMJJGSUTRBWGW-UHFFFAOYSA-N pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=CC=N1.OC(=O)C1=CC=CC=N1 AKMJJGSUTRBWGW-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Substances [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-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
- NFRRMEMOPXUROM-UHFFFAOYSA-N triethoxy-[1-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)C(CC)OCC1CO1 NFRRMEMOPXUROM-UHFFFAOYSA-N 0.000 description 1
- CFUDQABJYSJIQY-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CC(C)OCC1CO1 CFUDQABJYSJIQY-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- MQIOTYIMUKBZKQ-UHFFFAOYSA-N triethoxy-[7-(oxiran-2-ylmethoxy)heptyl]silane Chemical compound C(C1CO1)OCCCCCCC[Si](OCC)(OCC)OCC MQIOTYIMUKBZKQ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- ITQVMIOKEJEYEZ-UHFFFAOYSA-N trimethoxy-[7-(oxiran-2-ylmethoxy)heptyl]silane Chemical compound CO[Si](OC)(OC)CCCCCCCOCC1CO1 ITQVMIOKEJEYEZ-UHFFFAOYSA-N 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- MREDAUUVDJMZIU-UHFFFAOYSA-N trimethyl 5-(oxiran-2-ylmethoxy)pentyl silicate Chemical compound C(C1CO1)OCCCCCO[Si](OC)(OC)OC MREDAUUVDJMZIU-UHFFFAOYSA-N 0.000 description 1
- HADKRTWCOYPCPH-UHFFFAOYSA-M trimethylphenylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C1=CC=CC=C1 HADKRTWCOYPCPH-UHFFFAOYSA-M 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 229940094989 trimethylsilane Drugs 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
-
- 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
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Abstract
本发明公开了一种拒油涂布材料组合物,其特征在于其包含:(A)由以下通式(1)表示的具有键联至少一个或多个氟原子的烃基的烷氧基硅烷;Rf[-X-Y-SiR1 a(OR2)3-a]m (1)其中Rf表示烷基、烯基或芳烃基团,该基团具有至少一个或多个氟原子和1至20个碳原子;X表示氧原子或者含有氧原子的二价有机基团;Y表示以(CH(Z)-)n表示的间隔基团其中Z是取代基,可以是氢原子、卤素原子或者具有1至3个碳原子的烃基,n表示2至8的整数;R1、R2可以是具有1至10个碳原子的相同或者不同的烃基;m是1或2,a是0、1或2;和(B)缩合催化剂。
Description
本发明涉及一种具有拒油性的涂布材料组合物。由于得到的涂布材料具有较低的表面能并显示优异的拒油性,因此它可以用于各种不同的基材和应用,特别是用于硅橡胶。
硅橡胶具有许多优异的性能,因此可用于许多领域。然而,由于硅橡胶与油类相容,其抗油性和拒油性欠佳,这限制了其应用。为了解决如何使硅橡胶等基材表面具有抗油性和拒油性的问题,人们已经研究了许多不同的技术。一种赋予硅橡胶拒油性的已知方法是在形成硅橡胶的聚二甲硅氧烷骨架上引入氟代基团。例如,已知一种可固化的氟代聚醚硅橡胶,其主链中具有全氟聚醚结构(见专利文献1:日本专利申请未审公开2006-299109)。根据这种方法,由于引入的氟代基团的作用,可以使硅橡胶表面具有拒油性。然而,这些氟代聚醚化合物也存在着一些问题,它们都很复杂且不易制得;并且,为了达到效果,需要添加大量该化合物,经济实用性差。此外,在制备氟代聚醚化合物时需要使用氟基溶剂,这是该化合物的一个缺点。
另一种赋予硅橡胶拒油性的已知方法是使用在分子中具有可水解基团(如,氟代烷基、烷氧基甲硅烷基)的含氟化合物涂布在橡胶表面。例如,有人提出使用含氟化合物,这种含氟化合物在分子两端各有氟代烷基,并通过中间基团键联可水解基团如三甲氧基甲硅烷基(见日本专利申请未审公开2004-352742)。根据这种方法,在橡胶表面施用含有含氟化合物的单体溶液,与三甲基硅烷进行水解缩合反应,在目标制品表面上形成拒油表面处理层。然而,当用基于这种方法形成的化合物处理硅橡胶表面时,尽管可以显现出一定的抗油性,但拒油性不足,不能满足需要更高拒油性的应用的要求。
另一种赋予拒油性的已知方法是用氟代有机聚合物,如聚四氟乙烯或者聚四氟乙烯-全氟烷基乙烯醚共聚物表面涂布硅橡胶(见专利文献3:日本专利申请未审公开2003-171519)。尽管获得了良好的拒油性,这种方法仍存在一些问题:将这些氟代有机化合物涂布在硅橡胶表面时,需要使用特殊底漆,因此该方法不具备经济实用性;由于制备步骤数目增加而导致其复杂性增大;以及由于处理过程中需要将其暴露在于高温中,因此硅橡胶需要具有超过300℃的耐热性。
鉴于上述情况,本发明的目的是提供一种涂布材料组合物,当将这种涂布材料组合物施用于各种不同基材特别是硅橡胶的表面时,其呈现出优异的拒油性。
为解决上述问题,发明人经过努力研究取得了出人意料的发现:在金属、玻璃、塑料、橡胶表面上涂布具有含氟原子烃基和烷氧基甲硅烷基的化合物可赋予其优异的拒油性,所述含氟原子烃基通过具有特殊结构的有机基团相连。此外,发明人还发现当将该化合物涂布在硅橡胶材料表面时,它表现出极其优异的拒油性,从而实现了本发明。更具体地,本发明描述如下。
拒油涂布材料组合物,其特征在于其包含:
(A)由以下通式(1)表示的烷氧基硅烷,其具有键联了至少一个或多个氟原子的烃基;
Rf[-X-Y-SiR1 a(OR2)3-a]m (1)
其中
Rf表示烷基、烯基或者芳烃基,该基团具有至少一个或多个氟原子和1至20个碳原子;
X表示氧原子或者含有氧原子的二价有机基团;
Y表示以(CH(Z)-)n表示的间隔基团;
其中Z是取代基,选自氢原子、卤素原子或者具有1至3个碳原子的烃基,n表示2到8的整数;
R1和R2可以是具有1至10个碳原子的相同或不同的烃基;
m是1或2;
a是0、1或2;以及
(B)缩合催化剂。
在优选的实施方案中,该拒油涂布材料组合物的特征在于其进一步包含基于100重量份的组分(A),0.001至10,000重量份的(C):不含氟原子的由通式(2)表示的烷氧基硅烷和/或其水解-缩合产物,和/或基于100重量份的组分(A),0.001至10000重量份的硅树脂(D)。
SiR3 b(OR4)4-b (2)
其中,
R3表示不含氟原子且具有1至12个碳原子的烃基;
R4表示具有1至12个碳原子的烷基或者具有1至12个碳原子的酰基;
b表示0或1至3的整数。
在优选实施方案中,根据以上描述的拒油涂布材料组合物的特征在于通式(1)中的X是酯基。
根据本发明的该拒油涂布材料组合物适用于涂布硅橡胶。
由于本发明的涂布材料组合物呈现出优异的拒油性,该组合物可以应用于多种应用中,尤其是需要拒油性的硅橡胶应用中。例如,该涂布材料组合物可用作汽车、电子、电气、建筑等工业领域中的涂布材料。
下面对本发明进行更详细的说明。在本发明中用作组分(A)的氟化合物是为本发明的组合物赋予拒油性的必要组分。该含氟化合物为烷氧基硅烷,该烷氧基硅烷由以下通式(1)表示,且具有键联至少一个或多个氟原子的烃基。
Rf[-X-Y-SiR1 a(OR2)3-a]m (1)
在式(1)中,Rf表示烷基、烯基或芳烃基团,该基团具有至少一个或多个氟原子和1至20个碳原子。特别地,如果Rf是芳烃基团,Rf是如下一个基团:C6F5-、C6H4F-、C6H3F2-、C6H2F3-、C6H3FCl-、C6H3BrF-、C6H3FI-和C6H3(CF3)2-。
如果Rf是烷基,Rf是如下一个基团:CF3-、C2F5-、C3F7-、C4F9-、C5F11-、C6F13-、C7F15-、C8F17-、C9F19-、C10F21-、C11F23-、C12F25-、C13F27-、C14F29-、C15F31-、C16F33-、C17F35-、C2HF4-、C3HF6-、C4HF8-、C5HF10-、C6HF12-、C7HF14-、C8HF16-、C9HF18-、C10HF20-、C11HF22-、C12HF24-、CF3CH2-、C2F5-(CH2)s-(在这里,s表示1至8的整数,以下同样如此,如果有的话),C3F7-(CH2)s-、C4F9-(CH2)s-、C5F11-(CH2)s-、C6F13-(CH2)s-、C7F15-(CH2)s-、C8F17-(CH2)s-、C9F19-(CH2)s-、C10F21-(CH2)s-、C11F23-(CH2)s-和C12F25-(CH2)s-。
如果Rf是烯基,Rf是如下一个基团:CF3CF=CF-、CF3CF=CF-CF2-、CF3CF=CF-C2F4-、CF3CF=CF-C3F6-、CF3CF=CF-C4F8-、CF3CF=CF-C5F10-、CF3CF=CF-C6F12-、CF3CF=CF-C7F14-、CF3CF=CF-C8F16-、CF3CF=CF-C9F18-和CF3CF=CF-C10F20-。
如果Rf是如下举例说明的烷基,Rf可包括醚键、磺酰基、羧基或者其他卤素原子。这样的Rf的具体实例包括:CF3CF(-OCF3)-、CF3CF(-OCF3)-CF2-、CF3CF(-OCF3)-C2F4-、CF3CF(-OCF3)-C3F6-、CF3CF(-OCF3)-C4F8-、CF3CF(-OCF3)-C5F10-、CF3CF(-OCF3)-C6F12-、CF3CF(-OCF3)-C7F14-、CF3CF(-OCF3)-C8F16-、CF3CF(-OCF3)-C9F18-、CF3CF(-OCF3)-C10F20-、F-SO2-C2F4-、F-SO2-C3F6-、F-SO2-C4F8-、F-SO2-C5F10-、F-SO2-C6F12-、F-SO2-C7F14-、F-SO2-C8F16-、F-SO2-C9F18-、F-SO2-C10F20-、F-SO2-CtF2t-O-CuF2u-(t和u分别代表1至10的整数)、HOOC-C2F4-、HOOC-C3F6-、HOOC-C4F8-、HOOC-C5F10-、HOOC-C6F12-、HOOC-C7F14-、HOOC-C8F16-、HOOC-C9F18-、HOOC-C10F20-、C2F5-O-C2F4-、C3F7-O-C2F4-、C4F9-O-C2F4-、C5F11-O-C2F4-、C6F13-O-C2F4-、C7F15-O-C2F4-、C8F17-O-C2F4-、C9F19-O-C2F4-、C10F21-O-C2F4-、C11F23-O-C2F4-、C2BrF4-、C3BrF6-、C4BrF8-、C5BrF10-、C6BrF12-、C7BrF14-、C8BrF16-、C9BrF18-、C10BrF20-、C2ClF4-、C3ClF6-、C4ClF8-、C5ClF10-、C6ClF12-、C7ClF14-、C8ClF16-、C9ClF18-、C10ClF20-、C2IF4-、C3IF6-、C4IF8-、C5IF10-、C6IF12-、C7IF14-、C8IF16-、C9IF18-和C10IF20-。如果上述含氟原子的烃Rf是烷基或者烯基,Rf可以是直链或者支链的。
通式(1)中X表示氧原子或含有氧原子的二价有机基团。例如,X是选自-O-、-OC(O)-和-CH(-OH)-的间隔基团,其在通式(1)中作为键联到硅原子上的间隔基团Y与含氟原子基团Rf之间的间隔基团。
通式(1)中Y表示以-(CH(Z)-)n表示的间隔基团,其中Z是取代基,选自氢原子、卤素原子或者具有1至3个碳原子的烃基,n表示2到8的整数。Y的具体实例包括-(CH2)2-、-(CH2)3-、-(CH2)4-、-(CH2)5-、-(CH2)6-、-CH2-CH(CH3)-、-CH(CH3)-CH2-、-(CHF)2-、-(CHCl)2-、-(CHBr)2-、-(CHI)2-、-CH2-CHF-、-CH2-CHCl-、-CH2-CHBr-、-CH2-CHI-、-CHF-CHCl-、-CHF-CHBr-、-CHF-CHI-、-CHCl-CHBr-、-CHCl-CHI-和-CHBr-CHI-。
通式(1)中R1和R2可以是相同或不同的具有1至10个碳原子的烃基。R1优选是甲基,R2优选是甲基、乙基或者丙基。m是1或2,a是0、1或2。
上述含氟烷氧基硅烷中,为了赋予本发明中的硅烷组合物优异的拒油性,特别优选使用组分(A)中的X是酯基的烷氧基硅烷。其中具体实例包括:
C6F5-CH2-OC(O)-(CH2)2-Si(OCH3)3,
C6F5-CH2-OC(O)-(CH2)2-SiCH3(OCH3)2,
C6F5-CH2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
C6F5-CH2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
F-SO2-(CF2)4-(CH2)2-OC(O)-(CH2)2-Si(OCH3)3,
F-SO2-(CF2)4-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2,
F-SO2-(CF2)6-(CH2)2-OC(O)-(CH2)2-Si(OCH3)3,
F-SO2-(CF2)6-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2,
F-SO2-(CF2)8-(CH2)2-OC(O)-(CH2)2-Si(OCH3)3,
F-SO2-(CF2)8-(CH2)2-OC(O)(CH2)2-SiCH3(OCH3)2,
F-SO2-(CF2)4-(CH2)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
F-SO2-(CF2)4-(CH2)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
F-SO2-(CF2)6-(CH2)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
F-SO2-(CF2)6-(CH2)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
F-SO2-(CF2)8-(CH2)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
F-SO2-(CF2)8-(CH2)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
HOOC-(CF2)4-(CH2)2-OC(O)-(CH2)2-Si(OCH3)3,
HOOC-(CF2)4-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2,
HOOC-(CF2)6-(CH2)2-OC(O)-(CH2)2-Si(OCH3)3,
HOOC-(CF2)6-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2,
HOOC-(CF2)8-(CH2)2-OC(O)-(CH2)2-Si(OCH3)3,
HOOC-(CF2)8-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2,
HOOC-(CF2)4-(CH2)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
HOOC-(CF2)4-(CH2)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
HOOC-(CF2)6-(CH2)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
HOOC-(CF2)6-(CH2)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
HOOC-(CF2)8-(CH2)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
HOOC-(CF2)8-(CH2)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
CF3(CF2)3-(CH2)2-OC(O)-(CH2)2-Si(OCH3)3,
CF3(CF2)3-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2,
CF3(CF2)4-(CH2)2-OC(O)-(CH2)2-Si(OCH3)3,
CF3(CF2)4-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2,
CF3(CF2)5-(CH2)2-OC(O)-(CH2)2-Si(OCH3)3,
CF3(CF2)5-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2,
CF3(CF2)6-(CH2)2-OC(O)-(CH2)2-Si(OCH3)3,
CF3(CF2)6-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2,
CF3(CF2)7-(CH2)2-OC(O)-(CH2)2-Si(OCH3)3,
CF3(CF2)7-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2,
CF3(CF2)3-(CH2)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
CF3(CF2)3-(CH2)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
CF3(CF2)4-(CH2)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
CF3(CF2)4-(CH2)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
CF3(CF2)5-(CH2)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
CF3(CF2)5-(CH2)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
CF3(CF2)6-(CH2)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
CF3(CF2)6-(CH2)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
CF3(CF2)7-(CH2)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
CF3(CF2)7-(CH2)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
H(CF2)4-(CH2)2-OC(O)-(CH2)2-Si(OCH3)3,
H(CF2)4-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2,
H(CF2)5-(CH2)2-OC(O)-(CH2)2-Si(OCH3)3,
H(CF2)5-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2,
H(CF2)6-(CH2)2-OC(O)-(CH2)2-Si(OCH3)3,
H(CF2)6-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2,
H(CF2)7-(CH2)2-OC(O)-(CH2)2-Si(OCH3)3,
H(CF2)7-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2,
H(CF2)8-(CH2)2-OC(O)-(CH2)2-Si(OCH3)3,
H(CF2)8-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2,
H(CF2)4-(CH2)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
H(CF2)4-(CH2)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
H(CF2)5-(CH2)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
H(CF2)5-(CH2)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
H(CF2)6-(CH2)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
H(CF2)6-(CH2)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
H(CF2)7-(CH2)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
H(CF2)7-(CH2)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
H(CF2)8-(CH2)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
H(CF2)8-(CH2)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
(CF3)2CF-(CH2)2-OC(O)-(CH2)2-Si(OCH3)3,
(CF3)2CF-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2,
(CF3)2CFCF2-(CH2)2-OC(O)-(CH2)2-Si(OCH3)3,
(CF3)2CFCF2-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2,
(CF3)2CF-(CF2)2-(CH2)2-OC(O)-(CH2)2-Si(OCH3)3,
(CF3)2CF-(CF2)2-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2,
(CF3)2CF-(CF2)3-(CH2)2-OC(O)-(CH2)2-Si(OCH3)3,
(CF3)2CF-(CF2)3-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2,
CF3)2CF-(CF2)4-(CH2)2-OC(O)-(CH2)2-Si(OCH3)3,
(CF3)2CF-(CF2)4-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2,
(CF3)2CF-(CF2)5-(CH2)2-OC(O)-(CH2)2-Si(OCH3)3,
(CF3)2CF-(CF2)5-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2,
(CF3)2CF-(CH2)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
(CF3)2CF-(CH2)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
(CF3)2CFCF2-(CH2)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
(CF3)2CFCF2-(CH2)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
(CF3)2CF-(CF2)2-(CH2)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
(CF3)2CF-(CF2)2-(CH2)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
(CF3)2CF-(CF2)3-(CH2)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
(CF3)2CF-(CF2)3-(CH2)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
(CF3)2CF-(CF2)4-(CH2)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
(CF3)2CF-(CF2)4-(CH2)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
(CF3)2CF-(CF2)5-(CH2)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
(CF3)2CF-(CF2)5-(CH2)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
(OCH3)3Si-(CH2)2-(O)C-C6H4-C(CF3)2-C6H4-OC(O)-(CH2)2-Si(OCH3)3,
(OCH3)2CH3Si-(CH2)2-(O)C-C6H4-C(CF3)2-C6H4-OC(O)-(CH2)2-SiCH3(OCH3)2,
(OCH3)3Si-CH2-CH(CH3)-(O)C-C6H4-C(CF3)2-C6H4-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
(OCH3)2CH3Si-CH2-CH(CH3)-(O)C-C6H4-C(CF3)2-C6H4-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
(OCH3)3Si-(CH2)2-(O)C-(CF3)2-OC(O)-(CH2)2-Si(OCH3)3,
(OCH3)3Si-(CH2)2-(O)C-(CF3)3-OC(O)-(CH2)2-Si(OCH3)3,
(OCH3)3Si-(CH2)4-(O)C-(CF3)4-OC(O)-(CH2)2-Si(OCH3)3,
(OCH3)3Si-(CH2)2-(O)C-(CF3)5-OC(O)-(CH2)2-Si(OCH3)3,
(OCH3)3Si-(CH2)2-(O)C-(CF3)6-OC(O)-(CH2)2-Si(OCH3)3,
(OCH3)3Si-(CH2)2-(O)C-(CF3)7-OC(O)-(CH2)2-Si(OCH3)3,
(OCH3)2CH3Si-(CH2)2-(O)C-(CF3)2-OC(O)-(CH2)2-SiCH3(OCH3)2,
(OCH3)2CH3Si-(CH2)2-(O)C-(CF3)3-OC(O)-(CH2)2-SiCH3(OCH3)2,
(OCH3)2CH3Si-(CH2)2-(O)C-(CF3)4-OC(O)-(CH2)2-SiCH3(OCH3)2,
(OCH3)2CH3Si-(CH2)2-(O)C-(CF3)5-OC(O)-(CH2)2-SiCH3(OCH3)2,
(OCH3)2CH3Si-(CH2)2-(O)C-(CF3)6-OC(O)-(CH2)2-SiCH3(OCH3)2,
(OCH3)2CH3Si-(CH2)2-(O)C-(CF3)7-OC(O)-(CH2)2-SiCH3(OCH3)2,
(OCH3)2CH3Si-(CH2)2-(O)C-(CF3)8-OC(O)-(CH2)2-SiCH3(OCH3)2,
(OCH3)3Si-CH2-CH(CH3)-(O)C-(CF3)2-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
(OCH3)3Si-CH2-CH(CH3)-(O)C-(CF3)3-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
(OCH3)3Si-CH2-CH(CH3)-(O)C-(CF3)4-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
(OCH3)3Si-CH2-CH(CH3)-(O)C-(CF3)5-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
(OCH3)3Si-CH2-CH(CH3)-(O)C-(CF3)6-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
(OCH3)3Si-CH2-CH(CH3)-(O)C-(CF3)7-OC(O)-CH(CH3)-CH2-Si(OCH3)3,
(OCH3)2CH3Si-CH2-CH(CH3)-(O)C-(CF3)2-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
(OCH3)2CH3Si-CH2-CH(CH3)-(O)C-(CF3)3-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
(OCH3)2CH3Si-CH2-CH(CH3)-(O)C-(CF3)4-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
(OCH3)2CH3Si-CH2-CH(CH3)-(O)C-(CF3)5-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
(OCH3)2CH3Si-CH2-CH(CH3)-(O)C-(CF3)6-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,
(OCH3)2CH3Si-CH2-CH(CH3)-(O)C-(CF3)7-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2,和
(OCH3)2CH3Si-CH2-CH(CH3)-(O)C-(CF3)8-OC(O)-CH(CH3)-CH2-SiCH3(OCH3)2。
这些有机硅化合物可以容易地由已知合成方法制备。作为典型实例,可以通过氢硅烷化反应,在具有烯基的含氟原子有机化合物上加成具有Si-H基团的烷氧基硅烷,制得有机硅化合物。
虽然作为组分(A),对赋予本发明组合物优异的拒油性至关重要的这些含氟化合物可以单独使用,但为了进一步提高拒油效果,也可以组合使用选自其中的至少两种或更多种。
为了使本发明中组分(A)发生水解-缩合反应,本发明中作为组分(B)的缩合催化剂是必不可少的组分。该缩合催化剂可以选自酸催化剂、碱催化剂和有机金属化合物。可以使用的酸催化剂的实例包括选自有机酸和无机酸的一种、两种或更多种。有机酸的具体实例包括2-氨基乙基磷酸、肌苷酸、2-甘油酸、D-葡萄糖-1-磷酸、甲酸、草酸、乙酸、二氯乙酸、三氯乙酸、硝基乙酸、苦味酸、2-吡啶羧酸(2-pyridinecarboxylic acid)、三氟乙酸以及三氟甲基磺酸。无机酸的实例包括高氯酸、盐酸、氢溴酸、硝酸、硫酸和磷酸。
碱性催化剂的实例包括:诸如氢氧化钾、氢氧化钠和氢氧化锂的碱金属氢氧化物,诸如氢氧化钙和氢氧化钡的碱土金属氢氧化物,诸如氢氧化铵、三甲胺和三乙胺、吡啶和二甲基吡啶的胺类化合物,以及诸如四甲基氢氧化铵和四乙基氢氧化铵的季铵盐。
有机金属化合物的实例包括:金属醇盐,如具有金属原子B、Al、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Zn、Zr、Mo、Ru、Rh、Pd、Ag、Cd、Sn、Os、Ir、Hg或稀土元素原子的金属甲醇盐、金属乙醇盐或金属异丙醇盐;金属酸盐,如金属硬脂酸盐和金属辛酸盐;以及金属螯合物,如金属乙酰丙酮化合物、金属辛烯基乙醇酸酯或金属乙酰乙酸乙酯。从可获得性和反应适当性角度来看,优选B、Al、Ti和Zr金属醇盐、金属酸盐和金属螯合物。更优选四正丁氧基锆、四乙酰丙酮锆、四正丙氧基锆、四正丁氧基钛、二异丙氧基钛二(乙酰乙酸乙酯)、三乙酰乙酸乙酯铝、三乙酰丙酮铝和异丙醇硼。作为金属醇盐的醇,例如可以使用容易获得的异丙醇或丁醇。另外,考虑到这种金属醇盐在空气中的安全性,也可以使用人工合成或者从天然产物中提取的大分子醇。
基于100重量份的组分(A),作为组分(B)的缩合催化剂的重量份为0.001至100重量份,优选为0.01至20重量份。如果缩合催化剂的重量份低于0.001重量份,其作为缩合催化剂的效果不能充分体现,不能获得具有足够性能的固化膜。另外,如果催化剂用量超过100重量份,组合物的储存稳定性会变差。
优选地,本发明的涂布材料组合物还包含不含氟原子的烷氧基硅烷(C),和/或硅树脂(D)。这些组分具有可以与本发明的涂布材料组合物的必要组分(A)发生共水解-缩合反应,或者可以与组分(A)的水解-缩合产物非常相容的烷氧基甲硅烷基。这些组分可以使本发明的组合物对基材具有粘附性,也可以改善由本发明组合物形成的涂布膜的物理性质,如强度。
本发明的组分(C)是以通式(2)表示的不含氟原子的烷氧基硅烷,和/或其水解-缩合产物。
SiR3 b(OR4)4-b (2)
通式(2)中,
R3示具有1至12个碳原子的不含氟原子的烃基;
R4表示具有1至12个碳原子的烷基或具有1至12个碳原子的酰基;
b表示0或者1至3的整数。
优选地,R3是烷基、烯基或者芳烃基团。从水解-缩合反应的速率快的角度考虑,特别优选甲基或乙基。优选R4是甲基或乙基。以通式(2)表示的不含氟原子的烷氧基硅烷的具体实例包括四甲氧基硅烷、四乙氧基硅烷、甲基三甲氧基硅烷、甲基三乙氧基硅烷、乙基三甲氧基硅烷、乙基三乙氧基硅烷、苯基三甲氧基硅烷、苯基三乙氧基硅烷、二甲基二甲氧基硅烷、二乙基二甲氧基硅烷、二乙基二乙氧基硅烷、二苯基二甲氧基硅烷、二苯基二乙氧基硅烷、三甲基甲氧基硅烷和三乙基乙氧基硅烷。在这些物质中,特别优选甲基三甲氧基硅烷、乙基三甲氧基硅烷、甲基三乙氧基硅烷、乙基三乙氧基硅烷、四甲氧基硅烷和四乙氧基硅烷,因为它们的水解-缩合反应速率快。这些化合物可以单独使用,或者组合使用其中的两种或多种。
组分(C)可以是单一的不含氟原子的烷氧基硅烷,或者可以是不含氟原子的烷氧基硅烷和其水解-缩合产物的混合物,或者可以是不含氟原子的烷氧基硅烷的水解-缩合产物。本发明的不含氟原子的烷氧基硅烷的水解-缩合产物的聚合度较低,为2到20。优选地,不含氟原子的烷氧基硅烷的水解-缩合产物可以是四烷氧基硅烷的水解-缩合产物(称为烷基硅酸盐)。烷基硅酸盐的具体实例包括选自这些化合物的硅酸盐,其中烷基为甲基、乙基、异丙基、正丙基、异丁基或正丁基。其中,从水解-缩合反应速率快的角度来看,特别优选烷基为甲基或乙基的烷基硅酸盐。可以单独使用这种化合物的一种,或者两种或更多种组合使用。
基于100重量份的组分(A),组分(C)的用量为0.001至10000重量份,优选0.1至1000重量份,更优选1至200重量份。组分(C)可以原样添加,或可以通过使组分(C)与组分(A)的水解-缩合反应而使用。
下面将对作为本发明的组分(D)的硅树脂进行介绍。加入硅树脂不仅能改善从本发明中得到的涂布材料组合物与多种基材的粘附性,还能提高涂布材料的机械强度。本发明的硅树脂是有机聚硅氧烷,其中硅氧烷单元的平均组成由以下通式(3)表示,
R5 cSiO4-c/2 (3)
其中,
R5可以相同的或不同,表示具有1至12个碳原子的烷基、烯基或者芳烃基团;并且
c是0.5至2。
基于形成本发明的硅氧烷树脂的硅氧烷单元的总量,三有机硅氧烷单元的含量为0到80mol%,二有机硅氧烷单元的含量为0到60mol%,单有机硅氧烷单元的含量为0到80mol%,不含有机基团的SiO4/2单元的含量为0到60mol%。基于硅氧烷单元的总量,优选由10到80mol%的三有机硅氧烷单元和20到90mol%的不含有机基团的SiO4/2单元形成的聚有机硅氧烷树脂。这种聚有机硅氧烷树脂可以通过本领域技术人员已知的方法制备,使与组成单元相对应的氯代硅烷或烷氧基硅烷发生水解缩合反应。
此硅烷树脂的通式(3)中的R5可以相同或不同,表示烷基、烯基或者芳烃基,该基团具有1至12个碳原子。但是,优选地,分子中包括至少一个烯基。这是因为当将涂布材料组合物施用到硅橡胶表面时,由于烯基,可以获得较强的粘附性。
组分(D)可以单独使用,或者也可以两种或多种组合使用。基于100重量份的组分(A),组分(D)的用量为0.001至10000重量份,优选为0.1至1000重量份,更优选为1至200重量份。尽管组分(D)可以代替组分(C)使用,但由于这些组合物可以表现出协同效应,所以优选组分(C)和组分(D)一起使用。
在本发明中,根据实际应用,本发明的组合物可以通过分散或溶解在适当的溶剂中使用。优选使用的溶剂的实例包括:烃类,如己烷、辛烷、苯、甲苯、二甲苯、乙苯、环己烷和甲基环己烷;酯类,如乙酸甲酯、乙酸乙酯、乙酸丁酯和乙二醇单乙酸乙酯;酮类,如丙酮、丁酮、甲基异丁基酮、甲基戊基酮和环己酮;醇类,如甲醇、乙醇、丙醇、丁醇、戊醇、乙二醇单乙醚、乙二醇单丁醚;以及水。基于100重量份的组分(A),溶剂的用量为0.001至100000重量份,优选为0.1至10000重量份,更优选为1至1000重量份。
在本发明中,当使用水作为溶剂时,通过添加适量的表面活性剂并用均质器等强制搅拌生成的混合物,所述组合物可以作为乳化剂使用。在这种情况下,尽管可以使用多种表面活性剂,如阴离子表面活性剂、阳离子表面活性剂或非离子表面活性剂作为表面活性剂,但优选非离子表面活性剂。非离子表面活性剂的实例包括以式Ra-O-(CH2CH2O)m-(CHRxCH2O)n-H表示的聚氧化烯基烷基醚、以式RaCOO-(CH2CH2O)m-(CHRxCH2O)n-H表示的聚氧化烯基脂肪酸酯、以式RaN-[(CH2CH2O)m’-(CHRxCH2O)n’-H][CH2CH2O)m”-(CHRxCH2O)n”-H]表不的聚氧化烯基烷基胺、以式RaCON-[(CH2CH2O)m’-(CHRxCH2O)n’-H][CH2CH2O)m”-(CHRxCH2O)n”-H]表示的聚氧化烯基烷基酰胺、聚氧乙烯山梨醇脂肪酸酯以及甘油脂肪酸酯。
在本发明中,除以上所描述的组分(A)至(D),也可使用多种无机或有机填料用于改善涂膜的物理性质。这类填料的实例包括煅烧的二氧化硅、沉淀的二氧化硅、研磨的二氧化硅(ground silica)、硅藻土、铁氧化物、氧化锌、氧化钛、氧化镁、氧化钙、氢氧化镁、氢氧化钙、碳酸镁、碳酸钙、硫酸钡、硅酸镁(滑石)、硅酸铝(粘土)、偏硅酸钙、沸石、水滑石、石墨、炭黑、石英、氧化铝等。只要不影响本发明的目的,这些填料的用量是任意的。
在本发明中,除了上述组分(A)至(D),为了改善涂布材料对基材的粘附性或者涂布材料的物理性质,也可以使用硅烷偶联剂。这种硅烷偶联剂的具体实例包括硅烷化合物如乙烯基三甲氧基硅烷、乙烯基三乙氧基硅烷、乙烯基三乙酰氧基硅烷、乙烯基三甲氧基乙氧基硅烷、乙烯基二甲基乙氧基硅烷、乙烯基甲基二乙氧基硅烷、γ-氯丙基三甲氧基硅烷、γ-氯丙基三乙氧基硅烷、γ-氯丙基三乙酰氧基硅烷、3,3,3-三氟丙基三乙氧基硅烷、γ-甲基丙烯酰氧基丙基三甲氧基硅烷、γ-氨丙基三甲氧基硅烷、γ-氨丙基三乙氧基硅烷、γ-巯基三甲氧基硅烷、γ-巯基丙基三乙氧基硅烷、N-β-(氨乙基)-γ-氨丙基三甲基硅烷、β-氰基乙基三乙氧基硅烷、氯甲基三甲氧基硅烷、氯甲基三乙氧基硅烷、缩水甘油氧基甲基三甲氧基硅烷、缩水甘油氧基甲基三乙氧基硅烷、α-缩水甘油氧基乙基三甲氧基硅烷、α-缩水甘油氧基乙基三乙氧基硅烷、β-缩水甘油氧基乙基三甲氧基硅烷、β-缩水甘油氧基乙基三乙氧基硅烷、α-缩水甘油氧基丙基三甲氧基硅烷、α-缩水甘油氧基丙基三乙氧基硅烷、β-缩水甘油氧基丙基三甲氧基硅烷、β-缩水甘油氧基丙基三乙氧基硅烷、γ-缩水甘油氧基丙基三甲氧基硅烷、γ-缩水甘油氧基丙基三乙氧基硅烷、二乙氧基-3-缩水甘油氧基丙基甲基硅烷、二甲氧基-3-缩水甘油氧基丙基甲基硅烷、3-缩水甘油氧基丙基二甲氧基硅烷、γ-(甲基)丙烯酰氧丙基二甲基乙氧基硅烷、γ-(甲基)丙烯酰氧丙基甲基二乙氧基硅烷、γ-缩水甘油氧基丙基三丙氧基硅烷、γ-缩水甘油氧基丙基三丁氧基硅烷、γ-缩水甘油氧基丙基三甲氧基乙氧基硅烷、γ-缩水甘油氧基丙基三苯氧基硅烷、α-缩水甘油氧基丁基三甲氧基硅烷、α-缩水甘油氧基丁基三乙氧基硅烷、β-缩水甘油氧基丁基三甲氧基硅烷、β-缩水甘油氧基丁基三乙氧基硅烷、γ-缩水甘油氧基丁基三甲氧基硅烷、γ-缩水甘油氧基丁基三乙氧基硅烷、δ-缩水甘油氧基丁基三甲氧基硅烷、δ-缩水甘油氧基丁基三乙氧基硅烷、(3,4-环氧环己基)甲基三甲氧基硅烷、(3,4-环氧环己基)甲基三乙氧基硅烷、β-(3,4-环氧环己基)乙基三甲氧基硅烷、β-(3,4-环氧环己基)乙基三乙氧基硅烷、β-(3,4-环氧环己基)乙基三丙氧基硅烷、β-(3,4-环氧环己基)乙基三丁氧基硅烷、β-(3,4-环氧环己基)乙基三甲氧基乙氧基硅烷、β-(3,4-环氧环己基)乙基三苯氧基硅烷、γ-(3,4-环氧环己基)丙基三甲氧基硅烷、γ-(3,4-环氧环己基)丙基三乙氧基硅烷、δ-(3,4-环氧环己基)丁基三甲氧基硅烷、δ-(3,4-环氧环己基)丁基三乙氧基硅烷、γ-氯丙基甲基二甲氧基硅烷、γ-氯丙基甲基二乙氧基硅烷、二甲基二乙酰氧基硅烷、γ-甲基丙烯酰氧基丙基甲基二甲氧基硅烷、γ-甲基丙烯酰氧基丙基甲基二乙氧基硅烷、γ-巯基丙基甲基二甲氧基硅烷、γ-巯基丙基甲基二乙氧基硅烷、γ-氨丙基甲基二甲氧基硅烷、γ-氨丙基甲基二乙氧基硅烷、甲基乙烯基二甲氧基硅烷、甲基乙烯基二乙氧基硅烷、缩水甘油氧基甲基甲基二甲氧基硅烷、缩水甘油氧基甲基甲基二乙氧基硅烷、α-缩水甘油氧基乙基甲基二甲氧基硅烷、α-缩水甘油氧基乙基甲基二乙氧基硅烷、β-缩水甘油氧基乙基甲基二甲氧基硅烷、β-缩水甘油氧基乙基甲基二乙氧基硅烷、α-缩水甘油氧基丙基甲基二甲氧基硅烷、α-缩水甘油氧基丙基甲基二乙氧基硅烷、β-缩水甘油氧基丙基甲基二甲氧基硅烷、β-缩水甘油氧基丙基甲基二乙氧基硅烷、γ-缩水甘油氧基丙基甲基二甲氧基硅烷、γ-缩水甘油氧基丙基甲基二乙氧基硅烷、γ-缩水甘油氧基丙基甲基二丙氧基硅烷、γ-缩水甘油氧基丙基甲基二丁氧基硅烷、γ-缩水甘油氧基丙基甲基二甲氧基乙氧基硅烷、γ-缩水甘油氧基丙基甲基二苯氧基硅烷、γ-缩水甘油氧基丙基乙基二甲氧基硅烷、γ-缩水甘油氧基丙基乙基二乙氧基硅烷、γ-缩水甘油氧基丙基乙基二丙氧基硅烷、γ-缩水甘油氧基丙基乙烯基二甲氧基硅烷、γ-缩水甘油氧基丙基乙烯基二乙氧基硅烷、γ-缩水甘油氧基丙基苯基二甲氧基硅烷、γ-缩水甘油氧基丙基苯基二乙氧基硅烷和γ-(甲基)丙烯酰氧丙基三甲氧基硅烷。
对可施用本发明的涂布材料的基材没有特别限制,可以包括金属、玻璃、塑料、陶瓷、橡胶或者它们的组合(如复合材料、层压材料等)。因为基材可以呈现出拒油性,这是本发明的涂布材料的特性,所以优选在金属、塑料或橡胶上使用该涂布材料。特别是通过在硅橡胶上使用该涂布材料,可以显著提高硅橡胶的拒油性。
将本发明的组合物施用到各种基材表面的方法的实例包括手涂(使用已经浸泡该涂布溶液的棉布、纸、海绵等,将涂布溶液人工施用到基材上)、刷涂、浸渍涂布、流涂、淋涂、旋涂、喷涂、棒涂、辊涂、凹版涂布、气刀涂布等。
本发明的涂布材料组合物可以通过上述方法的一种将涂布材料组合物施用到基材表面上而在各种基材上形成拒油涂膜,然后使施用的涂布材料组合物进行水解缩合。水解缩合反应在0至250℃下进行。优选地,温度范围在20至220℃,更优选地,在40至200℃。作为具体的实例,拒油膜的形成包括:将涂布材料组合物施用在基材上,在25℃下放置1小时,在100℃下加热15分钟以初步固化该组合物,然后在200℃下加热4小时。
本发明涉及具有拒油性质的涂布材料组合物。由于获得的涂布材料具有低表面能,并呈现出优异的拒油性,所述涂布材料组合物可以用于多种应用中,特别是用于硅橡胶应用。例如,本发明涉及一种在汽车、电子、电气和建筑等工业领域中作为涂布材料的组合物。
实施例
通过参考下面的实施例和对比例,对本发明进行进一步描述。但本发明并不局限于以下工作实施例。实施例中的术语“份”指重量份。
接触角测量方法
使用由FACE Co.,Ltd生产的接触角测量仪CA-X150进行接触角测量。使用微量调节注射器(microsyringe)将一滴(约0.002cc)正十六烷(试剂纯,Kanto化学公司生成)滴在干净的涂布膜表面上,1分钟后即可测得接触角。5次测量的平均值作为接触角。
涂布材料组合物的制备
涂布材料组合物由以下方式制备。
制备实施例1
室温下在200mL的烧杯中加入甲苯(100份)。接着,加入5份以下式(i)表示的具有氟原子的烷氧基硅烷作为组分(A),7.5份四乙氧基硅烷作为组分(C),5份聚甲基硅氧烷树脂作为组分(D),(D)的组成为58mol%的(CH3)3SiO1/2单元、2mol%的(CH2=CH)(CH3)2SiO1/2单元和40mol%的SiO4/2单元,并且搅拌生成的混合物。接下来,边搅拌边添加2份钛酸四丁酯(titanium tetrabutoxy)作为组分(B),以制备根据本发明的涂布材料组合物。
C6F5-CH2-OC(O)-(CH2)2-SiCH3(OCH3)2 (i)
制备实施例2
按照制备实施例1中相同的方式制备涂布材料组合物,区别在于加入5份由以下式(ii)表示的具有氟原子的烷氧基硅烷作为组分(A)。
(OCH3)3-Si-(CH2)2-(O)C-(CF3)6-OC(O)-(CH2)2-Si(OCH3)3 (ii)
制备实施例3
按照制备实施例1中相同的方式制备涂布材料组合物,区别在于加入5份由以下式(iii)表示的具有氟原子的烷氧基硅烷作为组分(A)。
CF3(CF2)5-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2 (iii)
制备实施例4
按照制备实施例1中相同的方式制备涂布材料组合物,区别在于加入5份由以下式(iv)表示的具有氟原子的烷氧基硅烷作为组分(A)。
(CF3)2CF-(CF2)3-(CH2)2-OC(O)-(CH2)2-SiCH3(OCH3)2 (iv)
制备实施例5
按照制备实施例3中相同的方式制备涂布材料组合物,区别在于没有加入组分(D)。
制备实施例6
按照制备实施例1中相同的方式制备涂布材料组合物,区别在于没有加入组分(A)并加入12.5份的四乙氧基硅烷作为组分(C)。
涂布处理方法
制备玻璃测试片、SUS测试片以及硅橡胶测试片,这些测试片宽25mm、长50mm、厚2mm。然后用浸渍涂布法处理基材表面(室温下浸渍10秒,然后以1cm/s的速率升高)。将经处理的测试片置于湿度为50%、温度为25℃的环境中干燥1小时,然后在100℃下的空气循环式烘箱中加热15分钟以将组合物初步固化。然后将这些测试片置于设置为200℃的空气循环式烘箱中,并加热4小时形成固化膜。
实施例1
在玻璃测试片、SUS测试片和硅橡胶测试片的表面上都涂布制备实施例1的组合物,并形成固化膜。在室温下将测试片放置24小时,然后测量样品表面的接触角。结果如表1所示。
实施例2
玻璃测试片、SUS测试片和硅橡胶测试片的表面上都涂布制备实施例2的组合物,并形成固化膜。在室温下将测试片放置24小时,然后测量样品表面的接触角。结果如表1所示。
实施例3
玻璃测试片、SUS测试片和硅橡胶测试片的表面上都涂布制备实施例3的组合物,并形成固化膜。在室温下将测试片放置24小时,然后测量样品表面的接触角。结果如表1所示。
实施例4
玻璃测试片、SUS测试片和硅橡胶测试片的表面上都涂布制备实施例4的组合物,并形成固化膜。在室温下将测试片放置24小时,然后测量样品表面的接触角。结果如表1所示。
实施例5
玻璃测试片、SUS测试片和硅橡胶测试片的表面上都涂布制备实施例5的组合物,并形成固化膜。在室温下将测试片放置24小时,然后测量样品表面的接触角。结果如表1所示。
对比例1
玻璃测试片、SUS测试片和硅橡胶测试片的表面上都涂布制备实施例6的组合物,并形成固化膜。在室温下将测试片放置24小时,然后测量样品表面的接触角。结果如表1所示。
对比例2
在混合有具有氟原子的烷氧基硅烷的加成可固化型硅橡胶上,进行拒油测试。在通用的捏合机中加入100份聚二甲基硅氧烷(两端均由二甲基乙烯基甲硅烷基封端,25℃下粘度为20000mPa·s)、40份比表面积为200m2/g的煅烧的二氧化硅、8份六甲基二硅氮烷和1重量份去离子水,室温下搅拌得到的混合物并混合1小时。然后升温至150℃,加热并混合该混合物2小时。然后将混合物冷却至室温。在该混合物中加入3.1份聚甲基氢硅氧烷,其由67摩尔%的(CH3)HSiO2/2单元和33摩尔%的(CH3)2SiO2/2单元形成,并且其在25℃下的粘度为20mPa·s。然后加入0.8份用以延长室温下固化时间的乙炔醇(acetylene alcohol)以及0.3份乙烯基硅氧烷合铂络合物溶液(其中铂原子含量为0.5重量%),然后混合得到的混合物直至均匀。然后加入5份由以下式(i)表示的含氟原子的烷氧基硅烷作为本发明的组分(A),以制备硅橡胶组合物。将该硅橡胶组合物置于内部空腔尺寸为150mm×150mm×厚度2mm的模具中,在170℃下热压10分钟,制得片状样品。然后将该样品置于200℃的空气循环式烘箱中,加热4小时进行二次固化,从而制得拒油测试样品。接触角测量结果如表1所示。
C6F5-CH2-OC(O)-(CH2)2-SiCH3(OCH3)2 (i)
表1
Claims (4)
1.拒油涂布材料组合物,其特征在于其包含:
(A)由以下通式(1)表示的烷氧基硅烷,其具有键联至少一个或多个氟原子的烃基;
Rf[-X-Y-SiR1 a(OR2)3-a]m (1)
其中
Rf表示烷基、烯基或者芳烃基团,该基团具有至少一个或多个氟原子和1至20个碳原子;
X表示氧原子或者含有氧原子的二价有机基团;
Y表示以(CH(Z)-)n表示的间隔基团,
其中Z是取代基,选自氢原子、卤素原子或者具有1至3个碳原子的烃基,n表示2至8的整数;
R1、R2可以是具有1至10个碳原子的相同或者不同的烃基;
m是1或2,
a是0、1或2;和
(B)缩合催化剂。
2.根据权利要求1所述的拒油涂布材料组合物,其特征在于其进一步包含
基于100重量份的组分(A),0.001至10,000重量份的(C):由以下通式(2)表示的不含氟原子的烷氧基硅烷和/或其水解-缩合产物,和/或
基于100重量份的组分(A),0.001至10,000重量份的硅树脂(D),
SiR3 b(OR4)4-b (2)
其中
R3表示不含氟原子且具有1至12个碳原子的烃基,
R4表示具有1至12个碳原子的烷基或者具有1至12个碳原子的酰基,
b表示0或者1至3的整数。
3.根据权利要求1或2所述的拒油涂布材料组合物,其特征在于通式(1)中的X为酯基。
4.根据权利要求1至3任一项所述的拒油涂布材料组合物用于涂布硅橡胶的用途。
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CN109536014A (zh) * | 2017-09-22 | 2019-03-29 | 北京大学深圳研究生院 | 一种超硬韧性涂层的制备方法 |
CN115443175A (zh) * | 2020-02-19 | 2022-12-06 | 阿科玛法国公司 | 包含碘氟碳化合物的组合物 |
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US9731437B2 (en) * | 2013-11-22 | 2017-08-15 | Johnson & Johnson Vision Care, Inc. | Method of manufacturing hydrogel ophthalmic devices with electronic elements |
JP6704854B2 (ja) * | 2014-10-31 | 2020-06-03 | 住友化学株式会社 | 透明皮膜 |
CN106186029B (zh) * | 2016-07-11 | 2018-03-13 | 山东胜伟园林科技有限公司 | 一种用于盐碱地改良的脱硫石膏的无机改性方法 |
KR20180079034A (ko) * | 2016-12-30 | 2018-07-10 | 주식회사 동진쎄미켐 | 발수코팅 조성물 및 이로 코팅된 발수코팅 기재 |
JP6916313B2 (ja) * | 2017-03-03 | 2021-08-11 | インダストリー−ユニバーシティ・コーペレーション・ファウンデーション・ハニャン・ユニバーシティ・エリカ・キャンパス | 高分子基板の表面改質方法およびこれにより改質された表面を有する高分子基板 |
KR102145351B1 (ko) * | 2018-11-26 | 2020-08-19 | 한국생산기술연구원 | 나노입자를 포함하는 수지 조성물 및 그 제조방법 |
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JP2004352742A (ja) * | 2003-05-27 | 2004-12-16 | Fujikura Rubber Ltd | 表面処理組成物およびゴムの表面処理方法 |
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JP3570134B2 (ja) * | 1997-01-20 | 2004-09-29 | ソニー株式会社 | 防汚膜の形成方法及び表示素子用フィルター |
JP4126522B2 (ja) * | 2000-08-04 | 2008-07-30 | 信越化学工業株式会社 | 被膜形成用組成物用縮合物及び加水分解物の製造方法 |
JP4231983B2 (ja) * | 2000-12-22 | 2009-03-04 | 信越化学工業株式会社 | 水溶性撥水撥油処理剤及びその製造方法 |
JP3873727B2 (ja) | 2001-12-04 | 2007-01-24 | ダイキン工業株式会社 | 含フッ素材料分散水性組成物、被覆物品製造方法及び被覆物品 |
JP4446183B2 (ja) | 2005-04-21 | 2010-04-07 | 信越化学工業株式会社 | 硬化性フルオロポリエーテル系ゴム組成物及びゴム製品 |
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2011
- 2011-03-31 JP JP2011077795A patent/JP2012211263A/ja not_active Withdrawn
-
2012
- 2012-03-26 EP EP12161295A patent/EP2505626A1/en not_active Withdrawn
- 2012-03-28 US US13/432,046 patent/US20120251728A1/en not_active Abandoned
- 2012-03-30 KR KR1020120033172A patent/KR20120112225A/ko not_active Application Discontinuation
- 2012-03-31 CN CN2012101014638A patent/CN102732151A/zh active Pending
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JPH11217561A (ja) * | 1998-02-03 | 1999-08-10 | Shin Etsu Chem Co Ltd | 撥水膜復活剤 |
JP2004352742A (ja) * | 2003-05-27 | 2004-12-16 | Fujikura Rubber Ltd | 表面処理組成物およびゴムの表面処理方法 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN109536014A (zh) * | 2017-09-22 | 2019-03-29 | 北京大学深圳研究生院 | 一种超硬韧性涂层的制备方法 |
CN115443175A (zh) * | 2020-02-19 | 2022-12-06 | 阿科玛法国公司 | 包含碘氟碳化合物的组合物 |
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EP2505626A1 (en) | 2012-10-03 |
US20120251728A1 (en) | 2012-10-04 |
JP2012211263A (ja) | 2012-11-01 |
KR20120112225A (ko) | 2012-10-11 |
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