CA2308313A1 - Coatings that may comprise reactive silicon oligomers - Google Patents
Coatings that may comprise reactive silicon oligomers Download PDFInfo
- Publication number
- CA2308313A1 CA2308313A1 CA002308313A CA2308313A CA2308313A1 CA 2308313 A1 CA2308313 A1 CA 2308313A1 CA 002308313 A CA002308313 A CA 002308313A CA 2308313 A CA2308313 A CA 2308313A CA 2308313 A1 CA2308313 A1 CA 2308313A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- carbon atoms
- alkyl
- cycloaliphatic
- percent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000576 coating method Methods 0.000 title claims abstract description 25
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title description 17
- 229910052710 silicon Inorganic materials 0.000 title description 17
- 239000010703 silicon Substances 0.000 title description 17
- -1 acrylic polyol Chemical class 0.000 claims abstract description 79
- 239000000203 mixture Substances 0.000 claims abstract description 77
- 239000000178 monomer Substances 0.000 claims abstract description 72
- 229920005862 polyol Polymers 0.000 claims abstract description 62
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 28
- 239000011248 coating agent Substances 0.000 claims abstract description 18
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 17
- 229920000578 graft copolymer Polymers 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 77
- 229920000642 polymer Polymers 0.000 claims description 56
- 150000003077 polyols Chemical class 0.000 claims description 50
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 46
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 42
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 39
- 229910000077 silane Inorganic materials 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 150000001412 amines Chemical class 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 229910052698 phosphorus Inorganic materials 0.000 claims description 21
- 150000004756 silanes Chemical class 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 20
- 229920000728 polyester Polymers 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 150000002009 diols Chemical class 0.000 claims description 18
- 239000008199 coating composition Substances 0.000 claims description 16
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 150000001408 amides Chemical class 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 14
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 14
- 239000004202 carbamide Substances 0.000 claims description 14
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 13
- 125000004423 acyloxy group Chemical group 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
- 239000004417 polycarbonate Substances 0.000 claims description 12
- 239000003381 stabilizer Substances 0.000 claims description 12
- 229920000515 polycarbonate Polymers 0.000 claims description 11
- 229920000570 polyether Polymers 0.000 claims description 11
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 10
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 10
- 229920002635 polyurethane Polymers 0.000 claims description 10
- 239000004814 polyurethane Substances 0.000 claims description 10
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 9
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 9
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 229920000098 polyolefin Polymers 0.000 claims description 9
- 239000003431 cross linking reagent Substances 0.000 claims description 8
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 8
- 239000004952 Polyamide Substances 0.000 claims description 7
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 claims description 7
- 229920002647 polyamide Polymers 0.000 claims description 7
- BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical compound C=CC1CCC=CC1 BBDKZWKEPDTENS-UHFFFAOYSA-N 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 6
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical class O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229920005906 polyester polyol Polymers 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 239000003377 acid catalyst Substances 0.000 claims description 5
- 239000002245 particle Substances 0.000 claims description 5
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 claims description 4
- 229920001002 functional polymer Polymers 0.000 claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 claims description 3
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 229910052726 zirconium Inorganic materials 0.000 claims description 3
- BIGOJJYDFLNSGB-UHFFFAOYSA-N 3-isocyanopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCC[N+]#[C-] BIGOJJYDFLNSGB-UHFFFAOYSA-N 0.000 claims description 2
- INYHZQLKOKTDAI-UHFFFAOYSA-N 5-ethenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=C)CC1C=C2 INYHZQLKOKTDAI-UHFFFAOYSA-N 0.000 claims description 2
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 claims description 2
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 claims description 2
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 claims description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 3
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical group CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 claims 2
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims 2
- ICSWLKDKQBNKAY-UHFFFAOYSA-N 1,1,3,3,5,5-hexamethyl-1,3,5-trisilinane Chemical compound C[Si]1(C)C[Si](C)(C)C[Si](C)(C)C1 ICSWLKDKQBNKAY-UHFFFAOYSA-N 0.000 claims 1
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 claims 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims 1
- SXPLZNMUBFBFIA-UHFFFAOYSA-N butyl(trimethoxy)silane Chemical compound CCCC[Si](OC)(OC)OC SXPLZNMUBFBFIA-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229940087305 limonene Drugs 0.000 claims 1
- 235000001510 limonene Nutrition 0.000 claims 1
- 229910052719 titanium Inorganic materials 0.000 claims 1
- 239000010936 titanium Substances 0.000 claims 1
- 229920000877 Melamine resin Polymers 0.000 abstract description 11
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 abstract description 10
- 239000004971 Cross linker Substances 0.000 abstract description 3
- 230000000087 stabilizing effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 150000004072 triols Chemical class 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 13
- 229940063557 methacrylate Drugs 0.000 description 12
- 238000004132 cross linking Methods 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 150000001282 organosilanes Chemical class 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 238000007796 conventional method Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 239000004611 light stabiliser Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229920001228 polyisocyanate Polymers 0.000 description 7
- 239000005056 polyisocyanate Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical group O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 6
- 150000002118 epoxides Chemical class 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical class CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 6
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 5
- 229920000557 Nafion® Polymers 0.000 description 5
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 5
- 239000000470 constituent Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 238000006884 silylation reaction Methods 0.000 description 5
- 235000015096 spirit Nutrition 0.000 description 5
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 5
- 239000005052 trichlorosilane Substances 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 4
- 229920003270 Cymel® Polymers 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 238000003916 acid precipitation Methods 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000012975 dibutyltin dilaurate Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 3
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 3
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- HJZGNWSIJASHMX-UHFFFAOYSA-N butyl acetate;ethane-1,2-diol Chemical compound OCCO.CCCCOC(C)=O HJZGNWSIJASHMX-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000006459 hydrosilylation reaction Methods 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 2
- ZWNMRZQYWRLGMM-UHFFFAOYSA-N 2,5-dimethylhexane-2,5-diol Chemical compound CC(C)(O)CCC(C)(C)O ZWNMRZQYWRLGMM-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 2
- 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 2
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Classifications
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- 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
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
- C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C09D201/025—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3893—Low-molecular-weight compounds having heteroatoms other than oxygen containing silicon
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/675—Low-molecular-weight compounds
- C08G18/677—Low-molecular-weight compounds containing heteroatoms other than oxygen and the nitrogen of primary or secondary amino groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/71—Monoisocyanates or monoisothiocyanates
- C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
-
- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/062—Copolymers with monomers not covered by C09D133/06
- C09D133/066—Copolymers with monomers not covered by C09D133/06 containing -OH groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/003—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- 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
- C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
- C09D171/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/10—Block or graft copolymers containing polysiloxane sequences
-
- 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
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
- C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C09D201/10—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing hydrolysable silane groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
- C08K5/5465—Silicon-containing compounds containing nitrogen containing at least one C=N bond
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Paints Or Removers (AREA)
- Silicon Polymers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyethers (AREA)
- Polyurethanes Or Polyureas (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/969,198 | 1997-11-10 | ||
| US08/969,198 US6080816A (en) | 1997-11-10 | 1997-11-10 | Coatings that contain reactive silicon oligomers |
| PCT/US1998/024028 WO1999024517A2 (en) | 1997-11-10 | 1998-11-10 | Coatings that may comprrise reactive silicon oligomers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2308313A1 true CA2308313A1 (en) | 1999-05-20 |
Family
ID=25515295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002308313A Abandoned CA2308313A1 (en) | 1997-11-10 | 1998-11-10 | Coatings that may comprise reactive silicon oligomers |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6080816A (enExample) |
| EP (3) | EP1123952A3 (enExample) |
| JP (1) | JP2001522925A (enExample) |
| KR (1) | KR100577666B1 (enExample) |
| CN (1) | CN1134520C (enExample) |
| AU (1) | AU742662B2 (enExample) |
| BR (1) | BR9814011A (enExample) |
| CA (1) | CA2308313A1 (enExample) |
| DE (1) | DE69838456T2 (enExample) |
| WO (1) | WO1999024517A2 (enExample) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0936260A4 (en) * | 1996-10-31 | 2001-02-28 | Kaneka Corp | CURABLE COMPOSITION FOR FINISH COATING AND ARTICLES COATED WITH THIS COMPOSITION |
| IL137075A0 (en) * | 1998-02-06 | 2001-06-14 | Du Pont | Silicon reactive oligomers and coating compositions made therefrom |
| BR0012875A (pt) | 1999-07-30 | 2002-04-16 | Ppg Ind Ohio Inc | Composições de revestimento tendo resistência aperfeiçoada à arranhadura, substratos revestidos e métodos relacionados às mesmas |
| AU770696B2 (en) | 1999-07-30 | 2004-02-26 | Ppg Industries Ohio, Inc. | Cured coatings having improved scratch resistance, coated substrates and methods related thereto |
| US6623791B2 (en) | 1999-07-30 | 2003-09-23 | Ppg Industries Ohio, Inc. | Coating compositions having improved adhesion, coated substrates and methods related thereto |
| DE60033403T2 (de) | 1999-07-30 | 2007-10-31 | Ppg Industries Ohio, Inc. | Beschichtungszusammensetzungen mit verbesserter kratzfestigkeit, beschichtete oberfläche und verfahren zu deren herstellung |
| PT1228155E (pt) * | 1999-07-30 | 2009-06-03 | Ppg Ind Ohio Inc | Composições de revestimento flexíveis que apresentam resistência à riscagem melhorada, substratos revestidos e procedimentos associados |
| US6610777B1 (en) | 1999-07-30 | 2003-08-26 | Ppg Industries Ohio, Inc. | Flexible coating compositions having improved scratch resistance, coated substrates and methods related thereto |
| DE10132678A1 (de) * | 2000-07-26 | 2002-02-07 | Henkel Kgaa | Alkoxysilylgruppenhaltige Bindemittel und Bindemittelzusammensetzungen, Verfahren zu deren Herstellung und deren Verwendung |
| US6635341B1 (en) | 2000-07-31 | 2003-10-21 | Ppg Industries Ohio, Inc. | Coating compositions comprising silyl blocked components, coating, coated substrates and methods related thereto |
| US6767642B2 (en) * | 2002-03-11 | 2004-07-27 | E. I. Du Pont Nemours And Company | Preparation and use of crosslinkable acrylosilane polymers containing vinyl silane monomers |
| US6679943B1 (en) * | 2002-05-01 | 2004-01-20 | Basf Corporation | Coating containing adhesion promoting additive |
| US7597935B2 (en) | 2002-05-06 | 2009-10-06 | Lacks Enterprises, Inc. | Process for preparing chrome surface for coating |
| JP2005528445A (ja) * | 2002-05-31 | 2005-09-22 | マクマスター ユニバーシティー | シリカの前駆体としてのポリオール修飾シラン |
| DE10237270A1 (de) * | 2002-08-14 | 2004-03-04 | Consortium für elektrochemische Industrie GmbH | Silanvernetzbare Beschichtungsformulierungen |
| US20040157980A1 (en) * | 2003-02-06 | 2004-08-12 | Fox Michael D. | Coating composition with improved hardness, mar and etch resistance |
| US20040185269A1 (en) * | 2003-03-18 | 2004-09-23 | Loper Scott W. | Scratch and mar resistant low VOC coating composition |
| US20040239836A1 (en) * | 2003-03-25 | 2004-12-02 | Chase Lee A. | Metal plated plastic component with transparent member |
| US20040214017A1 (en) * | 2003-04-28 | 2004-10-28 | Uhlianuk Peter William | Coatings that contain monomeric and polymeric melamines with attached functional silane groups |
| DE10331456A1 (de) * | 2003-07-10 | 2005-02-24 | Basf Ag | (Meth)acrylsäureester alkoxilierter ungesättigter Polyolether und deren Herstellung |
| US20050074617A1 (en) * | 2003-10-02 | 2005-04-07 | Jun Lin | Clearcoat composition having both windshield sealant and recoat adhesion |
| US20050137322A1 (en) * | 2003-12-17 | 2005-06-23 | Roesler Richard R. | Silane modified two-component polyurethane coating |
| US7045588B2 (en) * | 2004-02-12 | 2006-05-16 | Basf Corporation | Polyester resin composition for use in a coating composition and method of preparing the same |
| JP4480719B2 (ja) * | 2004-05-07 | 2010-06-16 | 株式会社カネカ | 硬化性組成物 |
| US7871669B2 (en) * | 2004-08-30 | 2011-01-18 | E.I. Du Pont De Nemours And Company | Method for achieving a durable two-tone finish on a vehicle |
| US7838078B2 (en) * | 2004-08-30 | 2010-11-23 | E. I. Du Pont De Nemours And Company | Clearcoat composition compatible with both waterborne and solventborne basecoats |
| US7417105B2 (en) | 2005-02-15 | 2008-08-26 | Momentive Performance Materials Inc. | Crosslinkable silane-terminated polymer and sealant composition made with same |
| US7629396B2 (en) | 2005-02-23 | 2009-12-08 | E.I. Du Pont De Nemours And Company | Silicon-containing polytrimethylene homo- for copolyether composition |
| US20060189711A1 (en) * | 2005-02-23 | 2006-08-24 | Ng Howard C | Silicon-containing polytrimethylene homo- or copolyether composition |
| US7476344B2 (en) * | 2005-02-25 | 2009-01-13 | E.I. Du Pont De Nemours | Electrical apparatuses containing polytrimethylene homo- or copolyether glycol based electrical insulation fluids |
| WO2007016234A2 (en) * | 2005-07-29 | 2007-02-08 | E. I. Du Pont De Nemours And Company | Method for producing damage resistant multi-layer coatings on an automotive body or part thereof |
| US20090149554A1 (en) * | 2005-08-12 | 2009-06-11 | Shiseido Co., Ltd. | Water-soluble metal alcoholate derivatives, production methods thereof, and solid gelatinous external preparations containing the same |
| WO2008073340A1 (en) | 2006-12-07 | 2008-06-19 | E. I. Du Pont De Nemours And Company | Polymerization of acrylic polymers in reactive diluents |
| US8314201B2 (en) | 2007-11-30 | 2012-11-20 | The United States Of America As Represented By The Administration Of The National Aeronautics And Space Administration | Highly porous ceramic oxide aerogels having improved flexibility |
| US8258251B2 (en) * | 2007-11-30 | 2012-09-04 | The United States Of America, As Represented By The Administrator Of The National Aeronautics And Space Administration | Highly porous ceramic oxide aerogels having improved flexibility |
| BRPI0910266A2 (pt) * | 2008-03-18 | 2015-09-29 | Nano X Gmbh | método para a produção de tinta automotiva de alta resistência à abrasão, tinta automotiva e seu uso. |
| KR101824617B1 (ko) * | 2009-11-04 | 2018-03-14 | 삼성전자주식회사 | 유기실리케이트 화합물 및 이를 포함하는 조성물과 필름 |
| EP2361942A1 (en) * | 2010-02-25 | 2011-08-31 | Corning Incorporated | Non-shrinkable sol-gel-polymer hybrid and methods thereof |
| AU2012246784B2 (en) * | 2011-04-18 | 2015-07-16 | Bw Resins Ab | VOC free product |
| US8741393B2 (en) | 2011-12-28 | 2014-06-03 | E I Du Pont De Nemours And Company | Method for producing metalized fibrous composite sheet with olefin coating |
| JP6513346B2 (ja) * | 2014-07-07 | 2019-05-15 | タレックス光学工業株式会社 | 機能性積層眼鏡レンズ |
| WO2016010900A1 (en) | 2014-07-14 | 2016-01-21 | Momentive Performance Materials Inc. | Process for producing low-color and color-stable isocyanatoorganosilanes and products derived therefrom |
| JP6767485B2 (ja) | 2015-12-10 | 2020-10-14 | ダウ グローバル テクノロジーズ エルエルシー | 架橋性組成物及び当該架橋性組成物から作られたコーティング |
| WO2019081210A1 (en) * | 2017-10-27 | 2019-05-02 | Huntsman International Llc | CATALYSTS FOR MANUFACTURING OXAZOLIDINONE MATERIALS |
| JP6919626B2 (ja) * | 2018-05-17 | 2021-08-18 | 信越化学工業株式会社 | シルフェニレン骨格及びポリエーテル骨格を含むポリマー |
| CN108841000A (zh) * | 2018-05-22 | 2018-11-20 | 龙口德源高分子科技有限公司 | 一种乙烯基二甲氧基硅烷封端改性聚醚的合成方法 |
Family Cites Families (76)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1089519A (en) * | 1964-07-07 | 1967-11-01 | Albright & Wilson Mfg Ltd | Reinous organosilicon compositions |
| CA1101743A (en) * | 1974-05-24 | 1981-05-26 | Kevin M. Foley | Organo silane coupling agents |
| US4221697A (en) * | 1974-05-29 | 1980-09-09 | Imperial Chemical Industries Limited | Composite materials |
| US4101513A (en) * | 1977-02-02 | 1978-07-18 | Minnesota Mining And Manufacturing Company | Catalyst for condensation of hydrolyzable silanes and storage stable compositions thereof |
| US4146585A (en) * | 1977-03-02 | 1979-03-27 | Union Carbide Corporation | Process for preparing silane grafted polymers |
| US4267088A (en) * | 1979-09-13 | 1981-05-12 | Paul S. Kempf, Trustee or Successor Trustee | Solvent resistant inks and coatings |
| US4376190A (en) * | 1979-11-26 | 1983-03-08 | Minnesota Mining And Manufacturing Company | Cation complexes between cation guests and polymer hosts that contain cyclic ether units |
| US4367313A (en) * | 1981-06-10 | 1983-01-04 | Essex Chemical Corporation | Coating composition and method |
| US4377676A (en) * | 1981-09-23 | 1983-03-22 | Dow Corning Corporation | Non-precondensed silicone-alkyd resins and a method for their preparation |
| US4413086A (en) * | 1982-03-04 | 1983-11-01 | Ppg Industries, Inc. | Coating compositions containing organosilane-polyol |
| US4491650A (en) * | 1982-05-05 | 1985-01-01 | Essex Specialty Products, Inc. | Acrylic resin having pendant silane groups thereon, and methods of making and using the same |
| US4446292A (en) * | 1983-01-31 | 1984-05-01 | Ppg Industries, Inc. | Moisture curable compositions containing reaction products of hydrophobic polyols and monomer organosilicon-containing substances |
| US4501872A (en) * | 1983-01-31 | 1985-02-26 | Ppg Industries, Inc. | Moisture curable compositions containing reaction products of hydrophobic polyols and organosilicon-containing materials |
| US4467081A (en) * | 1983-01-31 | 1984-08-21 | Ppg Industries, Inc. | Gelable, silicate rich resins from hydrophobic polyols and volatile and/or incompatible organosilicates |
| US4732929A (en) * | 1983-01-31 | 1988-03-22 | Ppg Industries, Inc. | Silicon-containing polyols |
| US4613451A (en) * | 1983-01-31 | 1986-09-23 | Ppg Industries, Inc. | Gelable blends of organosilicon-containing materials and hydrophobic polyols |
| JPS59168074A (ja) * | 1983-03-16 | 1984-09-21 | Toyo Ink Mfg Co Ltd | オ−バ−プリントワニス |
| DE3580427D1 (de) * | 1984-08-31 | 1990-12-13 | Dainippon Ink & Chemicals | Bei zimmertemperatur haertbare harzzusammensetzung. |
| US4565760A (en) * | 1984-11-13 | 1986-01-21 | Xerox Corporation | Protective overcoatings for photoresponsive imaging members |
| US4652610A (en) * | 1986-01-03 | 1987-03-24 | Ppg Industries, Inc. | Compositions based on silicon-containing resins having hydrolyzable groups |
| US4678835A (en) * | 1986-01-30 | 1987-07-07 | Ppg Industries, Inc. | Coating composition containing an ungelled reaction product as a curative |
| US4739398A (en) * | 1986-05-02 | 1988-04-19 | Control Data Corporation | Method, apparatus and system for recognizing broadcast segments |
| JPH0721038B2 (ja) * | 1986-10-21 | 1995-03-08 | 高松油脂株式会社 | 硬化性飽和ポリエステル樹脂組成物 |
| US4810759A (en) * | 1986-12-16 | 1989-03-07 | E. I. Du Pont De Nemours And Company | Polyester graft copolymers, flexible coating compositions comprising same and branched polyester macromers for preparing same II |
| US4766185A (en) * | 1987-04-22 | 1988-08-23 | E. I. Du Pont De Nemours And Company | Polysiloxane graft copolymers, flexible coating compositions comprising same and branched polysiloxane macromers for preparing same - II |
| JP2559597B2 (ja) * | 1987-09-08 | 1996-12-04 | 関西ペイント株式会社 | 生物付着防止方法 |
| GB2212163B (en) * | 1987-11-12 | 1992-03-18 | Kansai Paint Co Ltd | Curable compositions and method of curing same |
| JP2668083B2 (ja) * | 1988-09-05 | 1997-10-27 | 関西ペイント株式会社 | 自動車用塗料組成物 |
| US5399607A (en) * | 1989-02-10 | 1995-03-21 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | One component composition containing a catalyst and having increased storability |
| WO1990009412A1 (fr) * | 1989-02-10 | 1990-08-23 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Preparation thermodurcissable |
| US5066722A (en) * | 1989-03-03 | 1991-11-19 | Nippon Paint Co., Ltd. | Heat-latent curing catalyst and resin compositions containing the same |
| CA2013949C (en) * | 1989-04-06 | 1999-08-24 | Toshiro Nambu | Thermosetting composition |
| US4992538A (en) * | 1989-06-05 | 1991-02-12 | Aqualon Company | Silated polysaccharides |
| JPH0397734A (ja) * | 1989-09-11 | 1991-04-23 | Kansai Paint Co Ltd | ポリシロキサン系オリゴマー、ポリシロキサン系樹脂組成物及び硬化性樹脂組成物 |
| JP3057573B2 (ja) * | 1989-10-26 | 2000-06-26 | 京セラミタ株式会社 | 電子写真感光体 |
| JP2783867B2 (ja) * | 1989-10-26 | 1998-08-06 | 三田工業株式会社 | 電子写真感光体 |
| EP0430156B1 (en) * | 1989-11-27 | 1995-02-01 | Toshiba Silicone Co., Ltd. | Coating composition, coated inorganic hardened product, and process for producing the product |
| US5190804A (en) * | 1989-11-27 | 1993-03-02 | Toshiba Silicone Co., Ltd. | Coated inorganic hardened product |
| US5066698A (en) * | 1990-05-10 | 1991-11-19 | E. I. Du Pont De Nemours And Company | Coating composition of an acrylic polymer, a crosslinking agent and a silane oligomer |
| CA2052842C (en) * | 1990-10-09 | 1999-08-24 | Hideyuki Ohnari | Curable resin and composition containing the same |
| US5219694A (en) * | 1990-10-09 | 1993-06-15 | Minolta Camera Kabushiki Kaisha | Toner for developing electrostatic latent image |
| JPH04200681A (ja) * | 1990-11-29 | 1992-07-21 | Matsushita Electric Works Ltd | 浄水装置 |
| US5250605A (en) * | 1990-12-17 | 1993-10-05 | E. I. Du Pont De Nemours And Company | Coating compositions comprising an organosilane polymer and reactive dispersed polymers |
| DE69206431T2 (de) * | 1991-01-28 | 1996-05-02 | Kanegafuchi Chemical Ind | Härtbare Zusammensetzung. |
| US5266715A (en) * | 1991-03-06 | 1993-11-30 | Ciba-Geigy Corporation | Glass coating with improved adhesion and weather resistance |
| US5182174A (en) * | 1991-05-13 | 1993-01-26 | E. I. Du Pont De Nemours And Company | Flexible etch-resistant finishes with siloxane cross-linking |
| USH1279H (en) * | 1991-05-13 | 1994-01-04 | Stephenson Maurice A S | Catalysts for curing silane coating compositions |
| JP2599517B2 (ja) * | 1991-07-03 | 1997-04-09 | 信越化学工業株式会社 | オルガノポリシロキサンの製造方法 |
| JPH058506A (ja) * | 1991-07-04 | 1993-01-19 | Toshiba Corp | 記録装置 |
| JPH05101116A (ja) * | 1991-10-04 | 1993-04-23 | Toshiba Corp | 電子図庫システムの端末装置 |
| JP3263414B2 (ja) * | 1991-10-15 | 2002-03-04 | 富士通株式会社 | レセプトチェック方法 |
| US5264530A (en) * | 1992-05-01 | 1993-11-23 | E. I. Du Pont De Nemours And Company | Process of polymerization in an aqueous system |
| ES2092177T3 (es) * | 1992-06-17 | 1996-11-16 | Philipp Rolf Kropf | Herramienta de elaboracion de huesos. |
| US5225510A (en) * | 1992-07-15 | 1993-07-06 | Dow Corning Corporation | Masonry treating composition and method |
| US5455080A (en) * | 1992-08-26 | 1995-10-03 | Armco Inc. | Metal substrate with enhanced corrosion resistance and improved paint adhesion |
| US5369153A (en) * | 1992-11-17 | 1994-11-29 | E. I. Du Pont De Nemours And Company | Acid-epoxy-melamine coating composition modified with a silane polymer |
| US5376706A (en) * | 1992-11-17 | 1994-12-27 | E. I. Du Pont De Nemours And Company | Anhydride epoxy coating composition modified with a silane polymer |
| US5376704A (en) * | 1992-11-17 | 1994-12-27 | E. I. Du Pont De Nemours And Company | Water-borne coating compositions comprising half esters of anhydride polymers crosslinked by epoxies |
| DE4239246C1 (de) * | 1992-11-21 | 1993-12-16 | Goldschmidt Ag Th | Verfahren zur Herstellung von SiH-Gruppen aufweisenden Organopolysiloxanen |
| US5230962A (en) * | 1992-12-11 | 1993-07-27 | E. I. Du Pont De Nemours And Company | Etch-resistant finishes with siloxane cross-linking |
| JPH06240000A (ja) * | 1993-02-17 | 1994-08-30 | Shin Etsu Chem Co Ltd | 分岐状オルガノポリシロキサンの製造方法 |
| JPH06340798A (ja) * | 1993-04-07 | 1994-12-13 | Asahi Glass Co Ltd | 変性シリコーンポリマーのエマルジョン及び乳化分散剤 |
| JP3278241B2 (ja) * | 1993-05-14 | 2002-04-30 | 富士写真フイルム株式会社 | 電子写真式製版印刷版の作成方法 |
| JPH06340709A (ja) * | 1993-06-02 | 1994-12-13 | Nippon Steel Corp | 有機無機融合体およびその製造方法 |
| JPH0762084A (ja) * | 1993-08-25 | 1995-03-07 | Asahi Glass Co Ltd | 硬化性組成物の製造法 |
| US5431791A (en) * | 1993-12-21 | 1995-07-11 | Basf Corporation | Cathodic electrodeposition method utilizing cyclic carbonate-curable coating composition |
| US5426168A (en) * | 1994-04-29 | 1995-06-20 | Dow Corning Corporation | Method of preparing an organically-modified, heat-curable silicone resin and the resin produced thereby |
| US5696179A (en) * | 1994-10-19 | 1997-12-09 | Dsm, N.V. | Silane oligomer and radiation curable coating composition containing the oligomer |
| US5506325A (en) * | 1994-12-15 | 1996-04-09 | Ppg Industries, Inc. | Coating composition having improved rheology control and copolymer, mixture and process therefor |
| AU718129B2 (en) * | 1995-05-02 | 2000-04-06 | E.I. Du Pont De Nemours And Company | Scratch-resistant coating composition |
| US6268456B1 (en) * | 1995-06-05 | 2001-07-31 | E. I. Du Pont De Nemours And Company | Coating composition containing silane functionality |
| JP2903297B2 (ja) * | 1995-12-04 | 1999-06-07 | エスケー化研株式会社 | 非汚染塗料組成物 |
| JPH09328652A (ja) * | 1996-06-10 | 1997-12-22 | Dainippon Ink & Chem Inc | 塗料用ポリウレタン樹脂組成物 |
| EP1396513B1 (en) * | 1997-04-21 | 2005-09-07 | Asahi Glass Company, Limited | Room temperature-setting composition |
| DE19736736A1 (de) * | 1997-08-23 | 1999-02-25 | Stefan Prof Dr Seeger | Verfahren zur Beschichtung von Oberflächen mit definierten Molekülschichten |
| US6045870A (en) * | 1997-09-03 | 2000-04-04 | Kansai Paint Co., Ltd. | High solid coating composition and method for forming topcoat using same |
-
1997
- 1997-11-10 US US08/969,198 patent/US6080816A/en not_active Expired - Fee Related
-
1998
- 1998-11-10 KR KR1020007005020A patent/KR100577666B1/ko not_active Expired - Fee Related
- 1998-11-10 WO PCT/US1998/024028 patent/WO1999024517A2/en not_active Ceased
- 1998-11-10 BR BR9814011-6A patent/BR9814011A/pt not_active Application Discontinuation
- 1998-11-10 DE DE69838456T patent/DE69838456T2/de not_active Expired - Fee Related
- 1998-11-10 EP EP01108867A patent/EP1123952A3/en not_active Withdrawn
- 1998-11-10 AU AU13976/99A patent/AU742662B2/en not_active Ceased
- 1998-11-10 EP EP01108866A patent/EP1123951A3/en not_active Withdrawn
- 1998-11-10 CA CA002308313A patent/CA2308313A1/en not_active Abandoned
- 1998-11-10 CN CNB988110024A patent/CN1134520C/zh not_active Expired - Fee Related
- 1998-11-10 JP JP2000520518A patent/JP2001522925A/ja active Pending
- 1998-11-10 EP EP98957807A patent/EP1029012B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999024517A3 (en) | 1999-09-02 |
| BR9814011A (pt) | 2000-09-26 |
| EP1029012B1 (en) | 2007-09-19 |
| EP1123952A3 (en) | 2002-12-04 |
| EP1123951A2 (en) | 2001-08-16 |
| KR20010031918A (ko) | 2001-04-16 |
| EP1123951A3 (en) | 2003-01-02 |
| KR100577666B1 (ko) | 2006-05-09 |
| CN1134520C (zh) | 2004-01-14 |
| JP2001522925A (ja) | 2001-11-20 |
| EP1029012A2 (en) | 2000-08-23 |
| US6080816A (en) | 2000-06-27 |
| DE69838456D1 (de) | 2007-10-31 |
| DE69838456T2 (de) | 2008-08-07 |
| AU742662B2 (en) | 2002-01-10 |
| AU1397699A (en) | 1999-05-31 |
| WO1999024517A2 (en) | 1999-05-20 |
| EP1123952A2 (en) | 2001-08-16 |
| CN1278851A (zh) | 2001-01-03 |
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