NO303643B1 - Primer for better adhesion of a silicone rubber coating to the substrate and its use - Google Patents
Primer for better adhesion of a silicone rubber coating to the substrate and its use Download PDFInfo
- Publication number
- NO303643B1 NO303643B1 NO923660A NO923660A NO303643B1 NO 303643 B1 NO303643 B1 NO 303643B1 NO 923660 A NO923660 A NO 923660A NO 923660 A NO923660 A NO 923660A NO 303643 B1 NO303643 B1 NO 303643B1
- Authority
- NO
- Norway
- Prior art keywords
- primer
- room
- chlorinated
- polydiorganosiloxane
- carbon atoms
- Prior art date
Links
- 239000004945 silicone rubber Substances 0.000 title claims description 32
- 239000000758 substrate Substances 0.000 title claims description 27
- 238000010073 coating (rubber) Methods 0.000 title claims description 10
- 229920002379 silicone rubber Polymers 0.000 title claims description 8
- 229920000098 polyolefin Polymers 0.000 claims description 30
- 239000000463 material Substances 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 229910000077 silane Inorganic materials 0.000 claims description 20
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 17
- 238000000576 coating method Methods 0.000 claims description 16
- 239000004215 Carbon black (E152) Substances 0.000 claims description 13
- 229930195733 hydrocarbon Natural products 0.000 claims description 13
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 11
- 239000013032 Hydrocarbon resin Substances 0.000 claims description 10
- 229920006270 hydrocarbon resin Polymers 0.000 claims description 10
- 239000011248 coating agent Substances 0.000 claims description 9
- 239000003921 oil Substances 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 230000037452 priming Effects 0.000 claims description 2
- 230000001737 promoting effect Effects 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 1
- -1 hydrocarbon radicals Chemical class 0.000 description 35
- 229920002631 room-temperature vulcanizate silicone Polymers 0.000 description 24
- 238000001723 curing Methods 0.000 description 21
- 239000000049 pigment Substances 0.000 description 17
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 229920001971 elastomer Polymers 0.000 description 8
- 229920001084 poly(chloroprene) Polymers 0.000 description 8
- 239000013535 sea water Substances 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 7
- 239000005060 rubber Substances 0.000 description 7
- 239000004793 Polystyrene Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920002545 silicone oil Polymers 0.000 description 6
- 230000003373 anti-fouling effect Effects 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 238000007654 immersion Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000004709 Chlorinated polyethylene Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229920001400 block copolymer Polymers 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000004848 polyfunctional curative Substances 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- 241000195493 Cryptophyta Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- 229920006311 Urethane elastomer Polymers 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- WTFXARWRTYJXII-UHFFFAOYSA-N iron(2+);iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+2].[Fe+3].[Fe+3] WTFXARWRTYJXII-UHFFFAOYSA-N 0.000 description 2
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229940057995 liquid paraffin Drugs 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000013008 moisture curing Methods 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 229920003216 poly(methylphenylsiloxane) Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 150000003141 primary amines Chemical group 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- QUASKMPFGHDRQD-UHFFFAOYSA-N 2-(3-triethoxysilylpropoxy)ethanamine Chemical compound CCO[Si](OCC)(OCC)CCCOCCN QUASKMPFGHDRQD-UHFFFAOYSA-N 0.000 description 1
- HWHBVXGWLQXNKT-UHFFFAOYSA-N 2-(triethoxysilylmethoxy)ethanamine Chemical compound CCO[Si](OCC)(OCC)COCCN HWHBVXGWLQXNKT-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- OJVVPBPWCPMEGX-UHFFFAOYSA-N 3-(3-triethoxysilylpropoxy)propan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCOCCCN OJVVPBPWCPMEGX-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 244000043261 Hevea brasiliensis 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
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- JJLKTTCRRLHVGL-UHFFFAOYSA-L [acetyloxy(dibutyl)stannyl] acetate Chemical compound CC([O-])=O.CC([O-])=O.CCCC[Sn+2]CCCC JJLKTTCRRLHVGL-UHFFFAOYSA-L 0.000 description 1
- TVJPBVNWVPUZBM-UHFFFAOYSA-N [diacetyloxy(methyl)silyl] acetate Chemical compound CC(=O)O[Si](C)(OC(C)=O)OC(C)=O TVJPBVNWVPUZBM-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-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
- 239000006227 byproduct Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229940125961 compound 24 Drugs 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- CGKJIOXZAXXOHB-UHFFFAOYSA-N diethoxymethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCOC(OCC)O[SiH2]CCCOCC1CO1 CGKJIOXZAXXOHB-UHFFFAOYSA-N 0.000 description 1
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 150000002118 epoxides Chemical group 0.000 description 1
- 229920006334 epoxy coating Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 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
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000004658 ketimines Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229910052759 nickel Inorganic materials 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
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 150000003097 polyterpenes Chemical class 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-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
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000011135 tin 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
- 150000003608 titanium Chemical class 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- QLAMKLOSSZSAKX-UHFFFAOYSA-N trimethoxy-[2-(6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2(C)OC21 QLAMKLOSSZSAKX-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
- 239000004711 α-olefin 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
- 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
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Laminated Bodies (AREA)
Description
Oppfinnelsen angår en primer for påføring på et substrat for å fremme adhesjon av et romtemperatur-vulkaniserbar (RTV) silikongummibelegg. The invention relates to a primer for application to a substrate to promote adhesion of a room temperature vulcanizable (RTV) silicone rubber coating.
RTV-silikongummibelegg blir påført undervannsoverflater, f.eks. skipsskrog, kjølevannsinnløp og utløp av kraftsta-sjoner, fiskefarmutstyr og andre undervanns- og skvulpe-soneoverflater av oljeproduksjonsplattformer, for å hindre tilgroing av akvatiske organismer, slik som alger og rur. RTV silicone rubber coatings are applied to underwater surfaces, e.g. ship hulls, cooling water inlets and outlets of power stations, fish farm equipment and other underwater and splash zone surfaces of oil production platforms, to prevent the growth of aquatic organisms, such as algae and algae.
Silikongummitilgroings-resistente belegg er beskrevet f.eks. i GB-A-1307001 , GB-A-1470465, GB-A-1581727, GB-A-2141436 , EP-A-16195 og US-A-3702778. RTV-silikongummibelegg har også blitt foreslått som belegg som hemmer adhesjon av is, f.eks. på overbygning og yttersider av skip. Silicone rubber fouling resistant coatings are described e.g. in GB-A-1307001, GB-A-1470465, GB-A-1581727, GB-A-2141436, EP-A-16195 and US-A-3702778. RTV silicone rubber coatings have also been proposed as coatings that inhibit adhesion of ice, e.g. on the superstructure and outer sides of ships.
Et problem ved anvendelse av slike RTV-silikongummibelegg er at det er vanskelig å feste tilstrekkelig til substratene. Dette problemet er diskutert i EP-A-16195 som foreslår påføring av RTV-silikongummi som en kledning på et stofflag. A problem with the use of such RTV silicone rubber coatings is that it is difficult to adhere sufficiently to the substrates. This problem is discussed in EP-A-16195 which proposes the application of RTV silicone rubber as a coating to a fabric layer.
Forskjellige primere har blitt foreslått for romtemperatur-vulkaniserbare silikongummiantitilgroinger. US-A-3702778 foreslår en tverrbindbar silikonpasta. EP-A-89066 foreslår en blanding av en epoksysilan og en silan som inneholder en umettet hydrokarbongruppe. JP-A-53-137231, JP-A-53-137233 og JP-A-53-137234 foreslår forskjellige elastomere materialer slik som polyuretan, naturgummi, klorpren eller neoprengummi eller butyral/silikongummi. EP-A-323906 og EP-A-329375 foreslår en silikonharpiks som inneholder en aminosilan. Various primers have been proposed for room temperature vulcanizable silicone rubber antifoulings. US-A-3702778 proposes a crosslinkable silicone paste. EP-A-89066 proposes a mixture of an epoxy silane and a silane containing an unsaturated hydrocarbon group. JP-A-53-137231, JP-A-53-137233 and JP-A-53-137234 suggest various elastomeric materials such as polyurethane, natural rubber, chloroprene or neoprene rubber or butyral/silicone rubber. EP-A-323906 and EP-A-329375 propose a silicone resin containing an aminosilane.
US-A-4070421 beskriver anvendelse av klorinert polyetylen som en primer for å forbedre adhesjon av belegg på polyolefin-overflater. US-A-4070421 describes the use of chlorinated polyethylene as a primer to improve adhesion of coatings on polyolefin surfaces.
En primer ifølge oppfinnelsen for påføring til et substrat for å fremme adhesjon av et RTV-silikongummibelegg omfatter: A primer according to the invention for application to a substrate to promote adhesion of an RTV silicone rubber coating comprises:
(A) et aminosilanmateriale som er (A) an aminosilane material which is
(i) en primær amin-funksjonell silan med formel: (i) a primary amine-functional silane of formula:
der radikalene R, som kan være like eller forskjellige, er enverdige hydrokarbonradikaler som har 1 til 12 karbonatomer og valgfritt inneholder en eterbinding; R<1>er et alkylenradikal som har 2 til 4 karbonatomer eller et toverdig alifatisk eterradikal som har 3 til 8 karbonatomer; R<2>er hydrogen eller et alkylenradikal med 2 til 4 karbonatomer endesluttet med en primær amingruppe; og x er 2 eller 3; eller (ii) reaksjonsproduktet av en primær amin-funksjonell silan med formel I med en epoksy-funksjonell silan med formelen: wherein the radicals R, which may be the same or different, are monovalent hydrocarbon radicals having 1 to 12 carbon atoms and optionally containing an ether bond; R<1>is an alkylene radical having 2 to 4 carbon atoms or a divalent aliphatic ether radical having 3 to 8 carbon atoms; R<2> is hydrogen or an alkylene radical of 2 to 4 carbon atoms terminated with a primary amine group; and x is 2 or 3; or (ii) the reaction product of a primary amine-functional silane of formula I with an epoxy-functional silane of formula:
der A er et epoksid-substituert enverdig hydrokarbonradikal som har 4 til 12 karbonatomer; radikalene B, som kan være like eller forskjellige er alkylradikaler som har 1 til 4 karbonatomer; og a er 0 eller 1; eller (iii) reaksjonsproduktet av en primær amin-funksjonell silan med formel I med en alfa-, omega-dihydroksy-polydimetylsiloksanolje med formel: wherein A is an epoxide-substituted monovalent hydrocarbon radical having 4 to 12 carbon atoms; the radicals B, which may be the same or different, are alkyl radicals having 1 to 4 carbon atoms; and a is 0 or 1; or (iii) the reaction product of a primary amine-functional silane of formula I with an alpha-, omega-dihydroxy-polydimethylsiloxane oil of formula:
der y er 2 til 60; (B) et klorinert polyolefin; og (C) en rom-temperaturherdbar polydiorganosiloksan, der aminosilanmaterialet (A) blir anvendt ved 0,1-50 vekt-96 where y is 2 to 60; (B) a chlorinated polyolefin; and (C) a room-temperature curable polydiorganosiloxane, wherein the aminosilane material (A) is used at 0.1-50 wt-96
basert på klorinert polyolefin (B) og rom-temperaturherdbar polydiorganosiloksan (C) blir anvendt ved 0,1-100 vektdeler pr. vektdel klorinert polyolefin (B). based on chlorinated polyolefin (B) and room-temperature curable polydiorganosiloxane (C) is used at 0.1-100 parts by weight per weight part chlorinated polyolefin (B).
Oppfinnelsen er også rettet mot anvendelse av primeren for grunning av et substrat før belegging med et rom-temperaturvulkaniserbart silikongummimateriale. The invention is also directed to the use of the primer for priming a substrate before coating with a room-temperature vulcanizable silicone rubber material.
I den primære amin-funksjonelle silan i formel I er radikalene R fortrinnsvis alkyl, f.eks. metyl, etyl, heksyl eller oktyl, aryl, f.eks. fenyl, eller aralkyl, f.eks. benzyl. Alkylenradikalet R<1>er fortrinnsvis -(CH2)3-, -(CHg^- eller metylsubstituert trimetylen, eller den kan være — (0112)3—0_ In the primary amine-functional silane of formula I, the radicals R are preferably alkyl, e.g. methyl, ethyl, hexyl or octyl, aryl, e.g. phenyl, or aralkyl, e.g. benzyl. The alkylene radical R<1> is preferably -(CH2)3-, -(CHg^- or methyl-substituted trimethylene, or it can be — (0112)3—0_
(CH2)2, -(CH2)3-0-(C<H>2)3- eller -CH2-0-(CH2 )2-. R<2>er fortrinnsvis hydrogen eller —CH2CH2NH2. Det kan være fordelaktig å separere et hvilket som helst eteroksygenatom i R og Ri med minst to karbonatomer fra det nærmeste hetero-atomet. Eksempler på primære amin-funksjonelle silaner med formel I er: (CH3O )3Si(CH2)3NH(CH2)2NH2; (CH3CH2OCH2CH20)3Si(CH2 )2NH2 ; (C2H50)3Si(CH2)3NH2; (CH30CH2CH20)3Si(CH2)3NH2; (C2H50 )3Si(CH2)30(CH2)3NH2; (C2H50)2C6H5Si(CE2)3NH2; (C2H50)3SiCH20(CH2)2NH2; (C2H50)3Si(CH2)30(CH2)2NH2; og (C2H50)2CH3Si(CH2)3NH2. Blandinger av to eller flere primære amin-funksjonelle silaner I kan bli anvendt hvis ønskelig. (CH2)2, -(CH2)3-O-(C<H>2)3- or -CH2-O-(CH2 )2-. R<2> is preferably hydrogen or —CH2CH2NH2. It may be advantageous to separate any ether oxygen atom in R and Ri by at least two carbon atoms from the nearest hetero atom. Examples of primary amine-functional silanes of formula I are: (CH 3 O ) 3 Si(CH 2 ) 3 NH(CH 2 ) 2 NH 2 ; (CH 3 CH 2 OCH 2 CH 2 O) 3 Si(CH 2 ) 2 NH 2 ; (C 2 H 5 O) 3 Si(CH 2 ) 3 NH 2 ; (CH 3 O CH 2 CH 2 O) 3 Si(CH 2 ) 3 NH 2 ; (C 2 H 5 O ) 3 Si(CH 2 ) 3 O(CH 2 ) 3 NH 2 ; (C 2 H 5 O) 2 C 6 H 5 Si(CE 2 ) 3 NH 2 ; (C 2 H 5 O) 3 SiCH 2 O(CH 2 ) 2 NH 2 ; (C 2 H 5 O) 3 Si(CH 2 ) 3 O(CH 2 ) 2 NH 2 ; and (C 2 H 5 O) 2 CH 3 Si(CH 2 ) 3 NH 2 . Mixtures of two or more primary amine-functional silanes I may be used if desired.
Den primære amin-funksjonelle silanen I blir fortrinnsvis anvendt slik den er i primer. Den kan imidlertid bli helt eller delvis erstattet ved et reaksjonsprodukt av den primære amin-funksjonelle silan I og en epoksy-funksjonell silan II. Gruppen A i den epoksy-funksjonelle silan II er fortrinnsvis en glysidoksy-substituert alkylgruppe, f.eks. 3-glykodoksy-propyl. Epoksyfunksjonell silan II kan f.eks. være 3- glysidoksypropyltrimetoksysilan, 3-glysidoksypropyldietoksy-metoksysilan, 2-g'lysidoksypropyltrimetoksysilan, 3-(3,4-apoksycykloheksyl)-propyltrimetoksysilan eller 2-(3 ,4-epoksy-4-metylcykloheksyl)-etyltrimetoksysilan. Eksempler på foretrukkede reaksjonsprodukter av en amin-funksjonell silan I og en epoksy-funksjonell silan II er: The primary amine-functional silane I is preferably used as it is in the primer. However, it can be completely or partially replaced by a reaction product of the primary amine-functional silane I and an epoxy-functional silane II. Group A in the epoxy-functional silane II is preferably a glycidoxy-substituted alkyl group, e.g. 3-Glycodoxy-propyl. Epoxy-functional silane II can e.g. be 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyldiethoxymethoxysilane, 2-glysidoxypropyltrimethoxysilane, 3-(3,4-apoxycyclohexyl)propyltrimethoxysilane or 2-(3,4-epoxy-4-methylcyclohexyl)ethyltrimethoxysilane. Examples of preferred reaction products of an amine-functional silane I and an epoxy-functional silane II are:
Aminosilan (I) og epoksysilan II kan bli reagert ved 20-80°C, fortrinnsvis ved å anvende 0,4-1,2 primære amingrupper av aminosilan I pr. epoksidgruppe i II. Aminosilane (I) and epoxysilane II can be reacted at 20-80°C, preferably by using 0.4-1.2 primary amine groups of aminosilane I per epoxide group in II.
I et annet alternativ er den primære amin-funksjonelle silan I erstattet fullstendig eller delvis ved et reaksjonsprodukt av den primære, amin-funksjonelle silan I og en alfa, omega-dihydroksypolydimetylsiloksan III. I og III kan bli reagert ved 20-80°C, fortrinnsvis ved å anvende 0,4-1,2 alkoksy-grupper av aminosilan I pr. silanolgruppe i III. In another alternative, the primary amine-functional silane I is replaced in whole or in part by a reaction product of the primary amine-functional silane I and an alpha, omega-dihydroxypolydimethylsiloxane III. I and III can be reacted at 20-80°C, preferably by using 0.4-1.2 alkoxy groups of aminosilane I per silanol group in III.
Klorinert polyolefin (B) har fortrinnsvis en molekylvekt fra 5000 til 50 000 og et klorinnhold fra 15 til 75 vekt-#, fortrinnsvis 17 til 40 vekt-#. Klorinerte polyolefiner er kommersielt tilgjengelige. De kan bli fremstilt ved å behandle et polyolefin med klor i nærvær av en peroksid-katalysator. Den klorinerte reaksjonen blir fortrinnsvis gjennomført i et oppløsningsmiddel for polyolefinutgangs-materialet. Polyolefinet er fortrinnsvis en poly(alfa-olefin) slik som polyetylen eller polypropylen. Polyolefinet kan være av høy eller lav tetthet, amorft eller krystallinsk. Det kan være en kopolymer av to eller flere olefiner, fortrinnsvis alfa-olefiner. Velegnede klorinerte polyolefiner er beskrevet f.eks. i US-A-3561965 og US-A-4070421. Chlorinated polyolefin (B) preferably has a molecular weight of from 5,000 to 50,000 and a chlorine content of from 15 to 75 wt-#, preferably 17 to 40 wt-#. Chlorinated polyolefins are commercially available. They can be prepared by treating a polyolefin with chlorine in the presence of a peroxide catalyst. The chlorinated reaction is preferably carried out in a solvent for the polyolefin starting material. The polyolefin is preferably a poly(alpha-olefin) such as polyethylene or polypropylene. The polyolefin may be of high or low density, amorphous or crystalline. It may be a copolymer of two or more olefins, preferably alpha-olefins. Suitable chlorinated polyolefins are described e.g. in US-A-3561965 and US-A-4070421.
Klorinert polyolefin (B) kan bli anvendt i forbindelse med en annen klorinert hydrokarbonharpiks, f.eks. en klorinert polyterpenharpiks eller klorinert polystyren. Polystyren er fortrinnsvis av lavmolekylvekt (mindre enn 5000). En slik klorinert hydrokarbonharpiks har fortrinnsvis en tilsvarende grad av klorinering som det klorinerte polyolefinet. Den klorinerte hydrokarbonharpiksen kan f.eks. bli anvendt i en mengde fra 1 til 100 vekt-# basert på klorinert polyolefin Chlorinated polyolefin (B) can be used in conjunction with another chlorinated hydrocarbon resin, e.g. a chlorinated polyterpene resin or chlorinated polystyrene. The polystyrene is preferably of low molecular weight (less than 5000). Such a chlorinated hydrocarbon resin preferably has a similar degree of chlorination as the chlorinated polyolefin. The chlorinated hydrocarbon resin can e.g. be used in an amount from 1 to 100 wt-# based on chlorinated polyolefin
(B). (B).
Aminosilanmateriale (A) blir generelt anvendt ved 0,1 til Aminosilane material (A) is generally used at 0.1 to
50 vekt-# basert på klorinert materiale (klorinert polyolefin (B) pluss en hvilken som helst annen klorinert hydrokarbonharpiks), fortrinnsvis 1 til 20 vekt-#. 50 wt-# based on chlorinated material (chlorinated polyolefin (B) plus any other chlorinated hydrocarbon resin), preferably 1 to 20 wt-#.
Den romtemperatur-herdbare polydiorganosiloksan (C) er fortrinnsvis en polydiorganosiloksan med viskositet 700 til 1 000 000 m-Pa-s ved 25°C. Den inneholder fortrinnsvis silisiumbundede hydroksylgrupper, f.eks. en alfa, omega-dihydroksypolydiorganosiloksan, eller silisiumbundede hydrolyserbare grupper, f.eks. en polydiorganosiloksan endesluttet med silisiumbundede hydrolyserbare grupper. Fortrinnsvis blir den dannet med gjentagende diorganosiloksy-enheter med formel -R<4>2S10- der radikalene R<4>, som kan være like eller forskjellige, representerer hydrokarbonradikaler som har 1 til 10 karbonatomer. Det er foretrukket at minst 50$ av radikalene R<4>er metylgrupper. Dihydroksypolydiorganosiloksan kan videre inneholde monoorganosiloksygrupper med formel R4Si01 g og/eller siloksygrupper med formel SiOg i en maksimum andel på 2% med hensyn på antall diorganosiloksy-grupper R<4>2SiO. The room temperature-curable polydiorganosiloxane (C) is preferably a polydiorganosiloxane having a viscosity of 700 to 1,000,000 m-Pa-s at 25°C. It preferably contains silicon-bonded hydroxyl groups, e.g. an alpha, omega-dihydroxypolydiorganosiloxane, or silicon-bonded hydrolyzable groups, e.g. a polydiorganosiloxane end-capped with silicon-bonded hydrolyzable groups. Preferably, it is formed with repeating diorganosiloxy units of the formula -R<4>2S10- where the radicals R<4>, which may be the same or different, represent hydrocarbon radicals having 1 to 10 carbon atoms. It is preferred that at least 50$ of the radicals R<4> are methyl groups. Dihydroxypolydiorganosiloxane can further contain monoorganosiloxy groups of the formula R4SiO1 g and/or siloxy groups of the formula SiOg in a maximum proportion of 2% with respect to the number of diorganosiloxy groups R<4>2SiO.
Hydrokarbonradikalene som er representert ved symbolet R<4>i di- og mono-organosiloksyenhetene kan passende bli valgt blant alkylradikaler slik som metyl, etyl, n-propyl, isopropyl, n-butyl, n-pentyl, n-heksyl, 2-etylheksyl eller n-oktyl, cykloalkylradikaler som har fra 4 til 8 karbonatomer slik som cyklopentyl, cykloheksyl eller metylcykloheksyl, alkenylradikaler som har fra 2 til 4 karbonatomer slik som vinyl, allyl eller buten-2-yl, og arylradikaler som har fra 6 til 8 karbonatomer, slik som fenyl, tolyl eller xylyl. The hydrocarbon radicals represented by the symbol R<4> in the di- and mono-organosiloxy units may suitably be selected from among alkyl radicals such as methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, n-hexyl, 2-ethylhexyl or n-octyl, cycloalkyl radicals having from 4 to 8 carbon atoms such as cyclopentyl, cyclohexyl or methylcyclohexyl, alkenyl radicals having from 2 to 4 carbon atoms such as vinyl, allyl or buten-2-yl, and aryl radicals having from 6 to 8 carbon atoms , such as phenyl, tolyl or xylyl.
Som foretrukkede eksempler på grupper som er representert ved R<4>2SiO kan følgende formler nevnes: As preferred examples of groups represented by R<4>2SiO the following formulas can be mentioned:
Et eksempel på en velegnet alfa, omega-dihydroksypolydimetylsiloksan er den som blir forhandlet av Rhone Poulenc under varemerket "48V 3500". An example of a suitable alpha, omega-dihydroxypolydimethylsiloxane is that marketed by Rhone Poulenc under the trademark "48V 3500".
Alfa, omega-dihydroksypolydiorganosiloksaner kan raskt bli fremstilt ved velkjente teknikker som beskrevet, f.eks. i FR-A-1134005, FR-A-1198749 og FR-A-1226745. Polydiorganosil-oksanene blir fortrinnsvis separert fra flyktige biprodukter før anvendelse, f.eks. ved fremgangsmåten som er beskrevet i US-A-4356116. Alpha, omega-dihydroxypolydiorganosiloxanes can be rapidly prepared by well-known techniques as described, e.g. in FR-A-1134005, FR-A-1198749 and FR-A-1226745. The polydiorganosyloxanes are preferably separated from volatile by-products before use, e.g. by the method described in US-A-4356116.
Foretrukkede alfa, omega-dihydroksypolydimetylsiloksaner består av etterfølgende grupper med formel (C^^SiO eller inneholder opp til 10$, f.eks. 2-10 mol-% av deres R<4->grupper som fenylgrupper, f.eks. i form av (C5H5^SiO-enheter. Preferred alpha, omega-dihydroxypolydimethylsiloxanes consist of trailing groups of formula (C^^SiO or contain up to 10$, e.g. 2-10 mol-% of their R<4-> groups as phenyl groups, e.g. in form of (C5H5^SiO units.
Alfa, omega-dihydroksypolydiorganosiloksaner blir generelt anvendt som et herdemiddel, f.eks. en forbindelse som inneholder minst to silisiumbundede hydrolyserbare grupper pr. molekyl. Eksempler på velegnede herdemidler er ketimin oksysilaner, acyloksysilaner og alkoksysilaner, tetraalkylti-tanater og aluminiumalkoholater. Alpha, omega-dihydroxypolydiorganosiloxanes are generally used as a curing agent, e.g. a compound containing at least two silicon-bound hydrolyzable groups per molecule. Examples of suitable curing agents are ketimine oxysilanes, acyloxysilanes and alkoxysilanes, tetraalkyl titanates and aluminum alcoholates.
Et ketiminoksysilanherdende middel inneholder fortrinnsvis minst to silisiumbundede hydrolyserbare ketiminoksygrupper pr. molekyl. Et slikt herdemiddel blir fortrinnsvis anvendt ved en til 18 vektdeler pr. 100 deler alfa- omega-dihydroksypolydiorganosiloksan. Det ketimonoksysilanherdende midlet kan ha generell formel: A ketiminoxysilane curing agent preferably contains at least two silicon-bound hydrolyzable ketiminoxy groups per molecule. Such a hardener is preferably used at one to 18 parts by weight per 100 parts alpha-omega-dihydroxypolydiorganosiloxane. The ketimonoxysilane curing agent may have the general formula:
der:" there:"
Y<1>representerer et hydrokarbonradikal som har 1 til 10 Y<1>represents a hydrocarbon radical having 1 to 10
karbonatomer, som kan bli substituert med halogen eller cyano; carbon atoms, which may be substituted with halogen or cyano;
Z<1>representerer et hydrolyserbart radikal med formel: Z<1>represents a hydrolyzable radical with formula:
der gruppen Z2 , som kan være lik eller forskjellig representerer C^-Cg hydrokarbonradikaler og E-<1->representerer et C4-C8alkylenradikal; gruppene Z<1>kan være like eller forskjellige; og where the group Z 2 , which may be the same or different, represents C 1 -C 8 hydrocarbon radicals and E 1 -> represents a C 4 -C 8 alkylene radical; the groups Z<1> may be the same or different; and
f representerer 0 eller 1. f represents 0 or 1.
Eksempler på gruppen Y<1>er de som er opplistet over som eksempler på gruppen R<4>i diorganosiloksyenhetene. Examples of the group Y<1> are those listed above as examples of the group R<4> in the diorganosiloxy units.
Eksempler på ketiminoksysilanherdende midler er de med formlene: Examples of ketiminoxysilane curing agents are those with the formulas:
Et acyloksysilanherdende middel kan f.eks. ha formelen: der R<5>er definert som for gruppen R<4>nevnt over, R<6>er et enverdig hydrokarbonradikal, f.eks. med opp til 8 karbonatomer, uten alifatisk umetting og a er 0 eller 1. Radikalene r<6>kan f.eks. være alkyl slik som metyl, etyl, n-propyl, n-butyl eller n-heksyl, cykloalkyl slik som cyklopentyl eller cykloheksyl, eller aryl slik som fenyl, tolyl eller xylyl. Eksempler på acyloksysilanherdende midler er: Et acyloksysilanherdemiddel kan f.eks. bli anvendt ved 2-20 vekt-# basert på alfa, omega-dihydroksypolydiorganosiloksan. Et alkoksysilanherdemiddel kan f.eks. være et tetraalkyl-ortosilikat (tetraalkoksysilan) slik som tetraetylortosilikat eller en alkyltrialkoksysilan slik som metyltrimetoksysilan, etyltrimetoksysilan eller metyltrietoksysilan. Alkoksysilanherdende midler slik som tetraetylortosilikat er særlig foretrukket for anvendelse med fuktighetsherdende polydi-organoslloksaner. An acyloxysilane curing agent can e.g. have the formula: where R<5> is defined as for the group R<4> mentioned above, R<6> is a monovalent hydrocarbon radical, e.g. with up to 8 carbon atoms, without aliphatic unsaturation and a is 0 or 1. The radicals r<6> can e.g. be alkyl such as methyl, ethyl, n-propyl, n-butyl or n-hexyl, cycloalkyl such as cyclopentyl or cyclohexyl, or aryl such as phenyl, tolyl or xylyl. Examples of acyloxysilane curing agents are: An acyloxysilane curing agent can e.g. be used at 2-20 wt-# based on alpha, omega-dihydroxypolydiorganosiloxane. An alkoxysilane curing agent can e.g. be a tetraalkyl orthosilicate (tetramethoxysilane) such as tetraethylorthosilicate or an alkyltrimethoxysilane such as methyltrimethoxysilane, ethyltrimethoxysilane or methyltriethoxysilane. Alkoxysilane curing agents such as tetraethylorthosilicate are particularly preferred for use with moisture-curing polydi-organosloxanes.
Romtemperatur-herdende polydiorganosiloksan (C) kan være fuktighetsherdende på grunn av atmosfærisk fuktighet er vanligvis tilstede når man belegger en marin overflate. En fuktighetsherdbar polydiorganosiloksan kan f.eks. ha hydrolyserbare endegrupper. Polydiorganosiloksan (C) som inneholder silisiumbundede hydrolyserbare grupper blir fortrinnsvis dannet ved å kombinere en alfa, omega-dihydroksypolydiorganosiloksan med en forbindelse som inneholder minst to silisiumbundede hydrolyserbare grupper pr. molekyl. Eksempler på velegnede forbindelser av denne type er ketiminoksysilaner og acyloksysilaner som er beskrevet over som herdemidler, f.eks. metyltriacetoksysilan, som danner polydiorganosiloksaner endesluttet med silisiumbundede hydrolyserbare ketiminoksy eller acyloksygrupper. Reaksjon mellom silisiumbundede hydroksylgrupper i alfa, omega-dihydroksypolydiorganosiloksan og de silisiumbundede hydrolyserbare gruppene i nevnte forbindelse foregår generelt når disse materialene blir kombinert, slik at polydiorganosiloksan (C) minst delvis blir endesluttet med silisiumbundede hydroksylgrupper. Room temperature curing polydiorganosiloxane (C) can be moisture curing due to atmospheric moisture is usually present when coating a marine surface. A moisture-curable polydiorganosiloxane can e.g. have hydrolyzable end groups. Polydiorganosiloxane (C) containing silicon-bonded hydrolyzable groups is preferably formed by combining an alpha, omega-dihydroxypolydiorganosiloxane with a compound containing at least two silicon-bonded hydrolyzable groups per molecule. Examples of suitable compounds of this type are ketiminoxysilanes and acyloxysilanes which are described above as curing agents, e.g. methyltriacetoxysilane, which forms polydiorganosiloxanes end-capped with silicon-bound hydrolyzable ketiminoxy or acyloxy groups. Reaction between silicon-bonded hydroxyl groups in alpha, omega-dihydroxypolydiorganosiloxane and the silicon-bonded hydrolyzable groups in said compound generally takes place when these materials are combined, so that polydiorganosiloxane (C) is at least partially terminated with silicon-bonded hydroxyl groups.
En alternativ polydiorganosiloksan (C) endesluttet med silisiumbundede hydrolyserbare grupper er en aminoendesluttet polydiorganosiloksan, f.eks. en alfa, omega-diaminopolydi-organosiloksan med formel: An alternative polydiorganosiloxane (C) end-capped with silicon-bonded hydrolyzable groups is an amino-terminated polydiorganosiloxane, e.g. an alpha, omega-diaminopolydi-organosiloxane of formula:
der R<4>er definert som over, n er et helt tall slik at polydiorganosiloksanet har en viskositet på 700-1 000 000 m'Pa*s ved 25°C, og R<7>og R<7>hver representerer hydrogen where R<4> is defined as above, n is an integer such that the polydiorganosiloxane has a viscosity of 700-1,000,000 m'Pa*s at 25°C, and R<7> and R<7> each represent hydrogen
eller en enverdig hydrokarbongruppe som har 1 til 10 karbonatomer. Det er mest å foretrekke at R<7>representerer hydrogen og R<8>representerer en alkylgruppe som har 2 til 6 karbonatomer, f.eks. etyl, propyl, isopropyl, n-butyl eller sek-butyl (but-2-yl). Eksempler på amin-endeavsluttende polydiorganosiloksaner blir forhandlet under varemerkene "Silgan 500" og ""Silgan 501J". or a monovalent hydrocarbon group having 1 to 10 carbon atoms. It is most preferred that R<7> represents hydrogen and R<8> represents an alkyl group having 2 to 6 carbon atoms, e.g. ethyl, propyl, isopropyl, n-butyl or sec-butyl (but-2-yl). Examples of amine-terminated polydiorganosiloxanes are sold under the trademarks "Silgan 500" and ""Silgan 501J".
Romtemperaturherdbar polydiorganosiloksan (C) blir Room temperature curable polydiorganosiloxane (C) becomes
anvendt ved 0,1 til 100 vektdeler, mer å foretrekke 1 til 50 vektdeler, pr. vektdel klorinert materiale (klorinert polyolefin (B) pluss en hvilken som helst annen klorinert hydrokarbonrest). used at 0.1 to 100 parts by weight, more preferably 1 to 50 parts by weight, per weight part chlorinated material (chlorinated polyolefin (B) plus any other chlorinated hydrocarbon residue).
Primeren kan inneholde en katalysator for romtemperatur-herding av polydiorganosiloksan. Eksempler på katalysatorer er metalliske og organometalliske salter av karboksyl syrer. Metalliske salter kan være salter av tinn, bly, nikkel, kobolt, jern, krom, sink eller mangan, f.eks. tinnoktoat. Foretrukkede organometalliske salter er diorganotinnkar-boksylatforbindelser slik som dibutyltinndilaurat eller dibutyltinnacetat. Organiske titanderivater som inneholder minst en -Ti-O-Si- eller -Ti-O-C-binding, f.eks. et alkanol-amintitanat, og organisk zirkoniumderivater kan bli anvendt som katalysator, som beskrevet i US-A-4525565. The primer may contain a catalyst for room temperature curing of polydiorganosiloxane. Examples of catalysts are metallic and organometallic salts of carboxylic acids. Metallic salts can be salts of tin, lead, nickel, cobalt, iron, chromium, zinc or manganese, e.g. tin octoate. Preferred organometallic salts are diorganotin carboxylate compounds such as dibutyltin dilaurate or dibutyltin acetate. Organic titanium derivatives containing at least one -Ti-O-Si- or -Ti-O-C bond, e.g. an alkanol-amine titanate, and organic zirconium derivatives can be used as catalyst, as described in US-A-4525565.
Primeren inneholder fortrinnsvis et organisk fortynningsmiddel som f.eks. kan være et alifatisk, cykloalifatisk eller aromatisk hydrokarbon som valgfritt blir halogenert slik som n-heptan, n-oktan, cykloheksan, metylcykloheksan, toluen, xylen, mesitylen, kumen, tetrahydronaftalen, perkloretylen, trikloretan, tetrakloretan, klorbenzen eller ortodiklor-benzen, et alifatisk eller cykloalifatisk keton slik som metyletylketon, metylisobutylketon, metylisoamylketon, cykloheksanon eller isoforon; en eter slik som en dialkyleter av etylenglykol eller propylenglykol, eller en ester slik som etylacetat, butylacetat eller etoksyetylacetat. Fortynnings- midlet er fortrinnsvis et oppløsningsmiddel for det klori-. nerte polyolefinet (B), inkludert en hvilken som helst annet klorinert hydrokarbonharpiks som er tilstede. Vektforholdet mellom fortynningsmiddel og klorinert polyolefin pluss en hvilken som helst annen klorinert hydrokarbonharpiks, er fortrinnsvis i området 1:3 til 20:1, mer å foretrekke 2:3 til 10:1. Vektforholdet av fortynningsmiddel til romtemperaturherdbar polydiorganosiloksan er vanligvis 1:50 til 20:1, fortrinnsvis 1:10 til 3:1. The primer preferably contains an organic diluent such as e.g. can be an aliphatic, cycloaliphatic or aromatic hydrocarbon which is optionally halogenated such as n-heptane, n-octane, cyclohexane, methylcyclohexane, toluene, xylene, mesitylene, cumene, tetrahydronaphthalene, perchlorethylene, trichloroethane, tetrachloroethane, chlorobenzene or orthodichlorobenzene, a aliphatic or cycloaliphatic ketone such as methyl ethyl ketone, methyl isobutyl ketone, methyl isoamyl ketone, cyclohexanone or isophorone; an ether such as a dialkyl ether of ethylene glycol or propylene glycol, or an ester such as ethyl acetate, butyl acetate or ethoxyethyl acetate. The diluent is preferably a solvent for the chlorine. nert polyolefin (B), including any other chlorinated hydrocarbon resin present. The weight ratio of diluent to chlorinated polyolefin plus any other chlorinated hydrocarbon resin is preferably in the range of 1:3 to 20:1, more preferably 2:3 to 10:1. The weight ratio of diluent to room temperature curable polydiorganosiloxane is usually 1:50 to 20:1, preferably 1:10 to 3:1.
Primeren kan bli fremstilt ved å blande aminosilanmaterialet (A) og det klorinerte polyolefinet (B) med romtemperaturherdbar polydiorganosiloksan (C). Det klorinerte polyolefin (B) og en hvilken som helst annen klorinert hydrokarbonharpiks som er tilstede blir fortrinnsvis oppløst i et organisk oppløsningsmiddel før blanding med aminosilanmateriale (A) og polydiorganosiloksan (C). The primer can be prepared by mixing the aminosilane material (A) and the chlorinated polyolefin (B) with room temperature curable polydiorganosiloxane (C). The chlorinated polyolefin (B) and any other chlorinated hydrocarbon resin present are preferably dissolved in an organic solvent prior to mixing with aminosilane material (A) and polydiorganosiloxane (C).
Primeren kan også inneholde additiver valgt blant pigmenter, mineralfyllstoffer, tiksotropiske midler, stabilisatorer, overflateaktive stoffer, antioksidanter og plastifiserings-midler. Det kan være fordelaktig å innbefatte fargepigmenter i primeren slik at den kan bli overdekket med et tilgroings-resistent lag av klar RTV-silikongummi. Når man inkorporerer pigmenter, kan det være nødvendig å ta forholdsregler for å unngå at noe av fuktigheten som er tilstede i pigmentet fremkaller for tidlig herding av romtemperaturherdbar polydiorganosiloksan (C). Den enkleste forhåndsregelen er å forsikre at et hvert pigment som blir anvendt er gjennom-gående tørt. Alternativt kan pigmentene bli dispergert i et fortynningsmiddel, fortrinnsvis en polydiorganosiloksan, som hemmer reaksjon av en hver fuktighet som er tilstede i pigmentet med romtemperaturherdbar polydiorganosiloksan (C). Pigmentet kan f.eks. bli dispergert i en ikke-reaktiv polydiorganosiloksanolje slik som metyl-endeavsluttet polydimetylsiloksanolje før pigmentet kommer i kontakt med romtemperaturherdbar polydiorganosiloksan (C) (som inkluderer et hvilket som helst herdemiddel til dette) og også fortrinnsvis før pigmentet kommer i kontakt med aminosilanmateriale (A). I en alternativ fremgangsmåte blir pigmentet dispergert i flytende hydroksyl-endeavsluttet polydiorganosiloksan før pigmentet kommer i kontakt med aminosilanmateriale (A) eller et hvilket som helst herdemiddel eller materiale som inneholder silisiumbundede hydrolyserbare grupper som danner deler av romtemperaturherdbar polydiorganosiloksan (C). Når denne alternative fremgangsmåten blir anvendt, vil de flytende hydroksylendeavsluttede polydiorganosiloksanet som blir anvendt som dispergeringsmiddel generelt bli samherdet med romtemperaturherdbart polydiorganosiloksan (C). Den kan i seg selv bli anvendt som romtemperaturherdbar polydiorganosiloksan (C), i forbindelse med et herdende middel som blir tilsatt senere. Det er imidlertid generelt foretrukket at en flytende hydroksylende-avsluttet polydiorganosiloksan som blir anvendt som dis-pergeringsmedium for pigmentene bare danner deler av polydiorganosiloksan (C); f.eks. kan den bli anvendt med en senere-tilsatt fuktighetsherdbar polydiorganosiloksan (C) endeavsluttet med hydrolyserbare grupper. The primer can also contain additives selected from among pigments, mineral fillers, thixotropic agents, stabilizers, surfactants, antioxidants and plasticizers. It may be advantageous to include color pigments in the primer so that it can be covered with a fouling-resistant layer of clear RTV silicone rubber. When incorporating pigments, it may be necessary to take precautions to avoid some of the moisture present in the pigment causing premature curing of room temperature curable polydiorganosiloxane (C). The simplest preliminary rule is to ensure that every pigment that is used is thoroughly dry. Alternatively, the pigments can be dispersed in a diluent, preferably a polydiorganosiloxane, which inhibits the reaction of any moisture present in the pigment with room temperature curable polydiorganosiloxane (C). The pigment can e.g. be dispersed in a non-reactive polydiorganosiloxane oil such as methyl-terminated polydimethylsiloxane oil before the pigment comes into contact with room temperature curable polydiorganosiloxane (C) (which includes any curing agent therefor) and also preferably before the pigment comes into contact with aminosilane material (A). In an alternative method, the pigment is dispersed in liquid hydroxyl-terminated polydiorganosiloxane before the pigment contacts aminosilane material (A) or any curing agent or material containing silicon-bonded hydrolyzable groups forming parts of room temperature curable polydiorganosiloxane (C). When this alternative method is used, the liquid hydroxyl-terminated polydiorganosiloxane that is used as a dispersant will generally be co-cured with room temperature curable polydiorganosiloxane (C). It can in itself be used as room-temperature curable polydiorganosiloxane (C), in connection with a curing agent that is added later. However, it is generally preferred that a liquid hydroxyl-terminated polydiorganosiloxane which is used as a dispersion medium for the pigments only forms parts of polydiorganosiloxane (C); e.g. it can be used with a later-added moisture-curable polydiorganosiloxane (C) end-capped with hydrolyzable groups.
Primerene er særlig effektive i å fremme adhesjon til organiske harpikssubstrater slik som neoprengummi, klorinert gummi, b1okk-kopolyrnergummi slik som polystyren/polybutadien eller polystyren/poly(etylenbutylen)gummi, polyuretaner, (både elastomerer og termoplastharpikser), epoksybelegg, vinylharpikser slik som vinylkloridpolymerer eller alkyd-harpikser. Disse harpiksene kan f.eks. være i form av bekledning i tilfelle med neopren og tilsvarende gummi, eller kan være tidligere-påførte belegg, f.eks. antikorrosive belegg som må bli dekket med en silikongummi-antitilgroings-farge, eller gamle antigroingsbelegg som må bli dekket over. Primerene fremmer også adhesjon til metallsubstrater slik som aluminium eller stål. The primers are particularly effective in promoting adhesion to organic resin substrates such as neoprene rubber, chlorinated rubber, block copolymer rubbers such as polystyrene/polybutadiene or polystyrene/poly(ethylenebutylene) rubber, polyurethanes, (both elastomers and thermoplastic resins), epoxy coatings, vinyl resins such as vinyl chloride polymers or alkyd resins. These resins can e.g. be in the form of cladding in the case of neoprene and corresponding rubber, or may be previously applied coatings, e.g. anti-corrosive coatings that need to be covered with a silicone rubber anti-fouling paint, or old anti-fouling coatings that need to be covered over. The primers also promote adhesion to metal substrates such as aluminum or steel.
Primeren kan bli påført substratet ved en hvilken som helst kjent beleggingsteknikk. Vanligvis blir den påført med sprøyte, pensel eller rull. The primer can be applied to the substrate by any known coating technique. It is usually applied by spray, brush or roller.
RTV-silikongummi-antigroresistente belegg som blir påført over primeren kan f.eks. være basert på en alfa, omega-dihydroksypolydiorganosiloksan som beskrevet over, anvendt med et herdemiddel valgt blant de som er beskrevet over og valgfritt en katalysator valgt fra de som er beskrevet over. Alternativt kan RTV-silikongummi være en polydiorganosiloksan endeavsluttet med silikon-bundede hydrolyserbare grupper som beskrevet over, f.eks. silikon-bundet ketiminoksy- eller acyloksygruppe. Det kan være foretrukket at herdemidlet eller silikon-bundede hydrolyserbare grupper i rom-temperaturherdbar diorganopolysiloksan (C) i primeren og herdemidlet eller silikon-bundede hydrolyserbare grupper i RTV-silikon-gummibelegget er de samme. RTV-silikongummibelegg innbefatter fortrinnsvis en ikke-reaktiv silikonolje, f.eks. med formel: QsSi-O-CSiQg-O-)nSiQ3, der hver gruppe Q representerer et hydrokarbonradikal som har 1-10 karbonatomer og n er et helt tall slik at silikonoljen har en viskositet på 20 til 5000 m*Pa*s. Minst 10$ av gruppene Q er generelt metylgrupper og minst 2% av gruppene Q er fortrinnsvis fenylgrupper. Det er mest å foretrekke at minst 25% av -SiQg-O-enhetene er metylfenylsiloksanenheter. Fortrinnsvis er den ikke-reaktive silikonoljen en metyl-terminert poly(metylfenylsiloksan). Oljen har fortrinnsvis en viskositet på 20 til 1000 nrPa*s og blir fortrinnsvis anvendt ved 1 til 5056, mest å foretrekke 2 til 20 vekt-% basert på RTV-silikongummi. Et eksempel på en foretrukket ikke-reaktiv silikonolje er den som forhandles med varemerket "Rhodorsil Huile 550". Ikke-reaktiv silikonolje forbedrer resistensen i sammensetningen mot akvatisk tilgroing. RTV silicone rubber anti-aging coatings that are applied over the primer can e.g. be based on an alpha, omega-dihydroxypolydiorganosiloxane as described above, used with a curing agent selected from those described above and optionally a catalyst selected from those described above. Alternatively, RTV silicone rubber can be a polydiorganosiloxane end-capped with silicone-bonded hydrolyzable groups as described above, e.g. silicone-bonded ketiminoxy or acyloxy group. It may be preferred that the hardener or silicone-bound hydrolyzable groups in room-temperature curable diorganopolysiloxane (C) in the primer and the hardener or silicone-bound hydrolyzable groups in the RTV silicone rubber coating are the same. RTV silicone rubber coatings preferably include a non-reactive silicone oil, e.g. with formula: QsSi-O-CSiQg-O-)nSiQ3, where each group Q represents a hydrocarbon radical having 1-10 carbon atoms and n is an integer so that the silicone oil has a viscosity of 20 to 5000 m*Pa*s. At least 10% of the groups Q are generally methyl groups and at least 2% of the groups Q are preferably phenyl groups. It is most preferred that at least 25% of the -SiQg-O units are methylphenylsiloxane units. Preferably, the non-reactive silicone oil is a methyl-terminated poly(methylphenylsiloxane). The oil preferably has a viscosity of 20 to 1000 nrPa*s and is preferably used at 1 to 5056, most preferably 2 to 20% by weight based on RTV silicone rubber. An example of a preferred non-reactive silicone oil is that sold under the trademark "Rhodorsil Huile 550". Non-reactive silicone oil improves the resistance of the composition to aquatic fouling.
I stedet for, eller i tillegg til ikke-reaktiv silikonolje, kan RTV-silikongummisammensetningen inneholde et ikke-reaktivt fluidorganisk hydrokarbon, f.eks. en smørende mineralolje slik som flytende parafin, en lavmolekylvekt-polybuten eller vaselin eller en flytende parafin/vaselin-blanding. Et slikt ikke-reaktivt fluidorganisk hydrokarbon er fortrinnsvis fraværende fra primeren. Instead of, or in addition to, non-reactive silicone oil, the RTV silicone rubber composition may contain a non-reactive fluid organic hydrocarbon, e.g. a lubricating mineral oil such as liquid paraffin, a low molecular weight polybutene or petroleum jelly or a liquid paraffin/petroleum mixture. Such a non-reactive fluid organic hydrocarbon is preferably absent from the primer.
Primeren forbedrer samlet adhesjon av RTV-silikongummi til substrater i en større grad enn det som kan bli oppnådd i fravær av en hvilken som helst av essensielle komponenter (A), (B) og (C). Aminosilanmaterialet (A) og klorinert polyolefin (B) sikrer adhesjon av primeren til hhv. RTV-silikongummi og til det organiske harpikssubstratet. Det er imidlertid funnet at når en sammensetning som omfatter aminosilanmaterialet (A), klorinert polyolefin (B) og oppløsningsmiddel blir påført mange organiske substrater, blir det raskt absorbert av substratet, slik at adhesjon av etterfølgende påført RTV-silikongummibelegg er dårlig dersom det ikke blir påført meget raskt. Rom-temperaturherdbart polydiorganosiloksan (C) motvirker tendensen til primærsam-mensetningen å bli absorbert av substratet, og tillater en mye lengre tidsperiode, f.eks. en uke eller ennå lenger, der overdekking med en RTV silikongummisammensetning kan bli oppnådd med god adhesjon. The primer improves overall adhesion of RTV silicone rubber to substrates to a greater extent than can be achieved in the absence of any of the essential components (A), (B) and (C). The aminosilane material (A) and chlorinated polyolefin (B) ensure adhesion of the primer to the RTV silicone rubber and to the organic resin substrate. However, it has been found that when a composition comprising the aminosilane material (A), chlorinated polyolefin (B) and solvent is applied to many organic substrates, it is rapidly absorbed by the substrate, so that adhesion of subsequently applied RTV silicone rubber coating is poor if not applied very quickly. Room temperature curable polydiorganosiloxane (C) counteracts the tendency of the primary composition to be absorbed by the substrate, allowing a much longer period of time, e.g. a week or even longer, where recoating with an RTV silicone rubber compound can be achieved with good adhesion.
Primeren ifølge oppfinnelsen har en mye større adhesjon til mange substrater, særlig neopren, klorpren eller hydrokarbon-gummi, enn en sammensetning som ikke inneholder klorinerte polyolefiner. På alle substrater inkludert de som har en epoksyharpiks der den enkle kombinasjon av rom-temperaturherdbar polydiorganosiloksan og aminosilanmaterialet gir god adhesjon, forbedrer det klorinerte polyolefinet resistensen mot sjøvannedsenkning, god adhesjon av primeren til substratet og av RTV-silikongummitoppbelegget til primeren blir opprettholdt selv etter 18 måneders eller lenger nedsenkning i sjøvann. The primer according to the invention has a much greater adhesion to many substrates, especially neoprene, chloroprene or hydrocarbon rubber, than a composition which does not contain chlorinated polyolefins. On all substrates including those having an epoxy resin where the simple combination of room temperature curable polydiorganosiloxane and the aminosilane material provides good adhesion, the chlorinated polyolefin improves resistance to seawater immersion, good adhesion of the primer to the substrate and of the RTV silicone rubber topcoat to the primer is maintained even after 18 months or longer immersion in seawater.
Oppfinnelsen blir illustrert ved følgende eksempler der deler og prosentdeler er ved vekt. The invention is illustrated by the following examples where parts and percentages are by weight.
Eksempel 1 Example 1
25 deler av en 40$ oppløsning i xylen av en klorinert polyetylen (klorinnhold 22$) ble blandet med 2 deler N-(2-aminoetyl )-3-aminopropyltrimetoksysilan og fortynnet med 73 deler xylen. 14 deler av den resulterende sammensetningen ble blandet med 61 deler av en rom-temperaturherdbar polydiorganosiloksansammensetning og 25 deler metylisoamylketonoppløsningsmiddel. Rom-temperaturherdbart polydiorganosiloksansammensetning omfatter en alfa, omega-dihydroksypolydimetylsiloksan anvendt med et ketiminoksysilanherdende middel. 25 parts of a 40% solution in xylene of a chlorinated polyethylene (chlorine content 22%) was mixed with 2 parts of N-(2-aminoethyl)-3-aminopropyltrimethoxysilane and diluted with 73 parts of xylene. 14 parts of the resulting composition was mixed with 61 parts of a room temperature curable polydiorganosiloxane composition and 25 parts of methyl isoamyl ketone solvent. The room temperature curable polydiorganosiloxane composition comprises an alpha, omega-dihydroxypolydimethylsiloxane used with a ketiminoxysilane curing agent.
Den resulterende primeren ble påført et neoprengummisubstrat, og også på substrater belagt med epoksyharpiks, polyuretan, vinylharpiks og alkydharpiks antikorrosive malinger, og til et substrat som har rester av en gammel antitilgroingsmaling basert på kolofonium, en vinylkloridkopolymer og kobberoksid. I alle tilfellene kunne belegget av primeren bli dekket over med en RTV-silikongummi tilgroings-resistent sammensetning basert på en alfa, omega-dihydroksypolydiorganosiloksan med et ketiminoksysilanherdende middel og en ikke-reaktiv poly(metylfenylsiloksan) olje ca. 10 minutter etter påføring av primeren med god adhesjon av RTV-sammensetningen, og kunne også bli dekket over med RTV-sammensetningen 24 timer senere med god adhesjon. The resulting primer was applied to a neoprene rubber substrate, and also to substrates coated with epoxy resin, polyurethane, vinyl resin, and alkyd resin anticorrosive paints, and to a substrate having remnants of an old antifouling paint based on rosin, a vinyl chloride copolymer, and copper oxide. In all cases, the coating of the primer could be covered with an RTV silicone rubber fouling-resistant composition based on an alpha, omega-dihydroxypolydiorganosiloxane with a ketiminoxysilane curing agent and a non-reactive poly(methylphenylsiloxane) oil approx. 10 minutes after applying the primer with good adhesion of the RTV compound, and could also be covered with the RTV compound 24 hours later with good adhesion.
Det overdekkede materialet ble senket i sjøvann. Adhesjon mellom primeren og substrater, og mellom RTV-silikongummitilgroings-resistent belegg og primer, forble sterk etter 18 måneders nedsekning i sjøvann. The covered material was submerged in seawater. Adhesion between the primer and substrates, and between RTV silicone rubber fouling-resistant coating and primer, remained strong after 18 months of seawater immersion.
Eksempel 2 Example 2
29,7 deler pigmenter og fyllstoffer (baryter, titandioksid, dampet silisiumdioksid og svart jernoksid) og 0,1 del dibutyltinndilauratherdende katalysator ble dispergert ved oppmaling i 6,7 deler ikke-reaktiv metyl-endeavsluttet polydimetylsiloksanolje og 10,6 deler metylisoamylketon-oppløsningsmiddel. Den resulterende pigmentendispersjonen ble blandet med 36,4 deler rom-temperaturherdet polydimetylsiloksan endeavsluttet med ketimnoksygrupper, 8,3 deler av oppløsningen med klorinert polyetylen og N-(2-aminoetyl)-3-aminopropyltrimetoksysilan beskrevet i eksempel 1 og 8,2 deler metylisoamylketon. 29.7 parts pigments and fillers (barytes, titanium dioxide, fumed silicon dioxide and black iron oxide) and 0.1 part dibutyl tin dilaurate curing catalyst were dispersed by grinding in 6.7 parts non-reactive methyl-terminated polydimethylsiloxane oil and 10.6 parts methyl isoamyl ketone solvent. The resulting pigment dispersion was mixed with 36.4 parts of room-temperature cured polydimethylsiloxane end-capped with ketimnoxy groups, 8.3 parts of the solution of chlorinated polyethylene and N-(2-aminoethyl)-3-aminopropyltrimethoxysilane described in Example 1 and 8.2 parts of methyl isoamyl ketone.
Den resulterende primeren ble påført epoksyharpiks, neoprengummi og uretangummisubstrater. Disse prøvene ble dekket over etter 16 til 48 timer med RTV-silikongummi fra eksempel 1. The resulting primer was applied to epoxy resin, neoprene rubber and urethane rubber substrates. These samples were covered after 16 to 48 hours with RTV silicone rubber from Example 1.
Det overdekkende materialet ble senket i sjøvann. Adhesjon mellom primeren og substrater, og mellom RTV-silikongummiti 1-groings-resistent belegg og primer, forble sterke etter 16 måneders nedsekning i sjøvann. The covering material was submerged in seawater. Adhesion between the primer and substrates, and between RTV silicone rubber ti 1 growth resistant coating and primer, remained strong after 16 months of seawater immersion.
Eksempel 3 Example 3
28,1 deler pigmenter og fyllstoff (titandioksid, baryter, svart jernoksid og dampet silisiumdioksid) ble dispergert ved oppmaling i 11,5 deler flytende hydroksyl-endeavsluttet polydimetylsiloksan med 0,5 deler fuktningshjelp og 11,4 deler metylisoamylketon. Den resulterende pigmentdispersjonen ble blandet med 7,6 deler av oppløsningen med klorinert polyetylen og N-(2-aminoetyl)-3-aminopropyltrimetoksysilan som beskrevet i eksempel 1, 30,9 deler rom-temperaturherdbar polydimetylsiloksan endeavsluttet med ketiminoksygrupper, 0,03 deler dibutyltinndilaurat og 10,0 deler metylisoamylketon. 28.1 parts pigments and fillers (titanium dioxide, barytes, black iron oxide and fumed silicon dioxide) were dispersed by grinding in 11.5 parts liquid hydroxyl-terminated polydimethylsiloxane with 0.5 parts wetting aid and 11.4 parts methyl isoamyl ketone. The resulting pigment dispersion was mixed with 7.6 parts of the solution of chlorinated polyethylene and N-(2-aminoethyl)-3-aminopropyltrimethoxysilane as described in Example 1, 30.9 parts of room-temperature curable polydimethylsiloxane end-capped with ketiminoxy groups, 0.03 parts of dibutyltin dilaurate and 10.0 parts methyl isoamyl ketone.
Den resulterende primeren ble påført substrater av epoksyharpiks, aluminium, uretangummi, neoprengummi, et substrat som har en rest av gammel antitilgroingsmaling som beskrevet i eksempel 1, polystyren/polybutadienblokkopolymergummi og polystyren/poly(etylen-butylen )blokkopolymergummi. Disse prøvene ble dekket over etter 16 til 48 timer med RTV-silikongummi i eksempel 1. The resulting primer was applied to substrates of epoxy resin, aluminum, urethane rubber, neoprene rubber, a substrate having a residue of old antifouling paint as described in Example 1, polystyrene/polybutadiene block copolymer rubber and polystyrene/poly(ethylene-butylene) block copolymer rubber. These samples were covered after 16 to 48 hours with RTV silicone rubber in Example 1.
De overdekkede materialene ble senket i sjøvann. Adhesjon mellom primeren og substratene, og mellom RTV-silikongummitilgroings-resistent belegg og primer, forble sterke etter 6 måneders nedsenkning i sjøvann. The covered materials were submerged in seawater. Adhesion between the primer and the substrates, and between the RTV silicone rubber fouling-resistant coating and the primer, remained strong after 6 months of seawater immersion.
Claims (11)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB909006840A GB9006840D0 (en) | 1990-03-27 | 1990-03-27 | Coating compositions |
PCT/GB1991/000454 WO1991014747A1 (en) | 1990-03-27 | 1991-03-26 | Coating composition |
Publications (3)
Publication Number | Publication Date |
---|---|
NO923660L NO923660L (en) | 1992-09-21 |
NO923660D0 NO923660D0 (en) | 1992-09-21 |
NO303643B1 true NO303643B1 (en) | 1998-08-10 |
Family
ID=10673349
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO923660A NO303643B1 (en) | 1990-03-27 | 1992-09-21 | Primer for better adhesion of a silicone rubber coating to the substrate and its use |
Country Status (8)
Country | Link |
---|---|
JP (1) | JP3205335B2 (en) |
KR (1) | KR0175648B1 (en) |
BR (1) | BR9106209A (en) |
CA (1) | CA2078144C (en) |
FI (1) | FI101717B (en) |
GB (1) | GB9006840D0 (en) |
NO (1) | NO303643B1 (en) |
PT (1) | PT97186B (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998058007A1 (en) * | 1997-06-17 | 1998-12-23 | Konishi Co., Ltd. | Process for the preparation of urethane resins and urethane resin compositions |
US6165620A (en) * | 1998-12-21 | 2000-12-26 | General Electric Company | Method of restoring damaged foul release coating area on a metallic surface, and surface obtained thereby |
AU2004278075B2 (en) * | 2003-10-03 | 2008-02-14 | Hempel A/S | A tie-coat composition comprising at least two types of functional polysiloxane compounds and a method for using the same for establishing a coating on a substrate |
US20090042042A1 (en) * | 2005-04-05 | 2009-02-12 | Chugoku Marine Paints, Ltd. | Tei Coat for Organopolysiloxane Antifouling Coat, Composite Coats, and Ships and Underwater Structures Covered with the Composite Coats |
EP3778810A4 (en) * | 2018-03-28 | 2021-12-22 | Nitto Denko Corporation | Undercoat layer-forming composition, undercoat layer, and coating film |
WO2022202807A1 (en) * | 2021-03-26 | 2022-09-29 | 日東電工株式会社 | Layered body and primer composition |
-
1990
- 1990-03-27 GB GB909006840A patent/GB9006840D0/en active Pending
-
1991
- 1991-03-26 JP JP50695091A patent/JP3205335B2/en not_active Expired - Lifetime
- 1991-03-26 CA CA002078144A patent/CA2078144C/en not_active Expired - Lifetime
- 1991-03-26 BR BR919106209A patent/BR9106209A/en not_active IP Right Cessation
- 1991-03-26 KR KR1019920702339A patent/KR0175648B1/en not_active IP Right Cessation
- 1991-03-27 PT PT97186A patent/PT97186B/en not_active IP Right Cessation
-
1992
- 1992-09-21 NO NO923660A patent/NO303643B1/en not_active IP Right Cessation
- 1992-09-25 FI FI924303A patent/FI101717B/en active
Also Published As
Publication number | Publication date |
---|---|
FI101717B1 (en) | 1998-08-14 |
KR930700617A (en) | 1993-03-15 |
FI924303A0 (en) | 1992-09-25 |
NO923660L (en) | 1992-09-21 |
PT97186B (en) | 1998-07-31 |
GB9006840D0 (en) | 1990-05-23 |
PT97186A (en) | 1991-11-29 |
JP3205335B2 (en) | 2001-09-04 |
FI101717B (en) | 1998-08-14 |
NO923660D0 (en) | 1992-09-21 |
CA2078144A1 (en) | 1991-09-28 |
FI924303A (en) | 1992-09-25 |
BR9106209A (en) | 1993-03-23 |
KR0175648B1 (en) | 1999-05-01 |
CA2078144C (en) | 2002-07-30 |
JPH05505845A (en) | 1993-08-26 |
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