CN100338161C - Ambient temperature curing coating composition - Google Patents
Ambient temperature curing coating composition Download PDFInfo
- Publication number
- CN100338161C CN100338161C CNB2004800031983A CN200480003198A CN100338161C CN 100338161 C CN100338161 C CN 100338161C CN B2004800031983 A CNB2004800031983 A CN B2004800031983A CN 200480003198 A CN200480003198 A CN 200480003198A CN 100338161 C CN100338161 C CN 100338161C
- Authority
- CN
- China
- Prior art keywords
- coating composition
- polysiloxane
- weight
- catalyzer
- acrylic
- 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.)
- Expired - Lifetime
Links
- 239000008199 coating composition Substances 0.000 title claims abstract description 107
- -1 polysiloxane Polymers 0.000 claims abstract description 114
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 95
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 54
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- 125000000524 functional group Chemical group 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 52
- 239000000178 monomer Substances 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 17
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 10
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical group [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 230000007704 transition Effects 0.000 claims description 5
- 238000007306 functionalization reaction Methods 0.000 claims description 3
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims 4
- 239000011253 protective coating Substances 0.000 claims 1
- 239000011248 coating agent Substances 0.000 description 31
- 238000000576 coating method Methods 0.000 description 31
- 239000003973 paint Substances 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 24
- 239000000126 substance Substances 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 12
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 11
- 239000003999 initiator Substances 0.000 description 11
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000000049 pigment Substances 0.000 description 10
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 9
- 239000004593 Epoxy Substances 0.000 description 9
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 230000037452 priming Effects 0.000 description 9
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- 150000001412 amines Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 5
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- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 239000003351 stiffener Substances 0.000 description 4
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- 239000011701 zinc Substances 0.000 description 4
- JFZBGARWAAJSSX-UHFFFAOYSA-N (1,3,3-trimethoxy-3-silylpropyl) 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OC(CC([SiH3])(OC)OC)OC JFZBGARWAAJSSX-UHFFFAOYSA-N 0.000 description 3
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 3
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- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- 238000007599 discharging Methods 0.000 description 3
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- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical class CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
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- 239000002184 metal Substances 0.000 description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
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- 150000003839 salts Chemical class 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
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- 229920002554 vinyl polymer Polymers 0.000 description 3
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- 235000019352 zinc silicate Nutrition 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920004482 WACKER® Polymers 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
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- 230000032683 aging Effects 0.000 description 2
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- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
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- 239000007789 gas Substances 0.000 description 2
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
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- 239000004922 lacquer Substances 0.000 description 2
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
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- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 150000003609 titanium compounds Chemical class 0.000 description 2
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- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 1
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- 150000007527 lewis bases Chemical class 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- NHBRUUFBSBSTHM-UHFFFAOYSA-N n'-[2-(3-trimethoxysilylpropylamino)ethyl]ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCNCCN NHBRUUFBSBSTHM-UHFFFAOYSA-N 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- AHBPBADERZDJKT-UHFFFAOYSA-N pentane-2,3-dione zirconium Chemical compound [Zr].C(C)C(=O)C(=O)C AHBPBADERZDJKT-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000962 poly(amidoamine) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 229910052718 tin Inorganic materials 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
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 description 1
Images
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
- 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
- C09D133/08—Homopolymers or copolymers of acrylic acid esters
-
- 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
- C09D143/00—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 containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Coating compositions based on derivatives of such polymers
- C09D143/04—Homopolymers or copolymers of monomers containing silicon
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of 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; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
Abstract
Ambient temperature curing coating composition comprising - a branched alkoxy-functional polysiloxane having the formula R2-O-[Si(R1)2-O]n-R2, wherein each R1 is selected from the group consisting of alkyl, aryl, and alkoxy groups having up to six carbon atoms, and Osi(OR3)3 groups, wherein each R3 independently has the same meaning as R1, each R2 is selected from the group consisting of hydrogen and alkyl and aryl groups having up to six carbon atoms, and wherein n is selected such that the molecular weight of the polysiloxanes is in the range of from 500 to about 2,000, - a catalyst, and - an acrylic polymer. The acrylic polymer is substantially free of functional groups that can react with the polysiloxane or with the catalyst in the coating composition.
Description
The present invention relates to a kind of room-temperature-curable coating composition that comprises polysiloxane and acrylic polymers.It is that for example the hardness of faster drying of composition and solidified coating strengthens based on the advantage in the coating composition of polysiloxane that acrylic polymers is added.In addition, replace the part polysiloxane with acrylic polymers and also have the advantage of saving cost.
The room-temperature-curable composition that comprises polysiloxane and acrylic polymers is known.For example, US 4,138, and 387 disclose the composition that comprises the acrylic polymers solid particulate that is dispersed in the organopolysiloxane liquid.Described composition is to be cured as the dispersion of elongation at break for the rubber of about 120-about 190%.These compositions are usually too soft and too pliable and tough and can not be used as finishing paint or priming paint, because they are destroyed easily.
WO 99/31179 discloses a kind of encapsulant composition that is dispersed in the solid particulate that contains low Tg polymkeric substance and high-tg polymer in the polysiloxane that comprises.Solid particulate can be an acrylic copolymer.The elongation at break of this curing sealant is generally about 250-about 1600%.These compositions are usually too soft and too pliable and tough and can not be used as finishing paint or priming paint, because they are destroyed easily.
US 5,530,063 disclose a kind ofly comprise linear organopolysiloxane, can be that the polymkeric substance that has ethylenical unsaturated double bonds, epoxy compounds, epoxy compounds of acrylic polymers is with solidifying agent and the linear organopolysiloxane composition with curing catalysts.This coating can be used as for example sealing agent, tackiness agent or coating composition.The elongation at break of the gained coating of reporting in the document is greater than 300%.These compositions are usually too soft and too pliable and tough and can not be used as finishing paint or priming paint, because they are destroyed easily.
WO 01/51575 discloses a kind of acrylic polymers of polysiloxane, glycidyl-functionalised and curing coating composition at room temperature of stiffening agent of comprising.The shortcoming of this coating composition is that it need be packed in so-called double pack system; Stiffening agent separates packing with polysiloxane.This is disadvantageous, because comprised the packing of stiffening agent and comprise polysiloxane and the necessary thorough mixing of the packing of the polymkeric substance of glycidyl-functionalised before using said composition.And after mixing the shelf lives short, promptly about half an hour was to 4 hours at the most.This is that each component begins reaction in hold-up vessel because after each component is mixed.Another shortcoming is that stiffening agent is very important to the ratio of other component, and all the elements thing in therefore should be noted that an all the elements thing in the packing and another being packed mixes mutually.
EP 1 063 270 discloses the composition that comprises organopolysiloxane resin, acrylic resin, organic titanate, silane or its partial hydrolysate and organic liquid.This silane can be tetraalkoxysilane.The organic group of polysiloxane can be acyclic alkyl, univalent alicyclic hydrocarbon radical and univalent aromatic hydrocarbyl.Do not mention or advise functional group for the organic group on the polysiloxane as alkoxyl group.Described composition can be used as paint base composition and is used for the hardenable silicone elastomer of room temperature is adhered to various base materials.
GB 1,504, and 363 disclose a kind of water proof exterior wall wall guard lacquer that comprises acrylic polymers, polysiloxane and catalyzer.This polysiloxane has lower molecular weight, but does not further specify for the molecular weight of the polysiloxane in the said composition.It is said that this lacquer has high base-material content and low solvent, but the composition among the embodiment comprises the solvent of about 50 weight %.Because the concern for the volatile solvent of discharging into the atmosphere increases in recent years, thereby has just had the volatile organic solvent content with coating composition to reduce to the needs that are lower than 50 weight %.
US 4,965, and 312 disclose a kind of coating paint composition that forms refractory coating.This paint composition is the nonaqueous dispersion of vinyl polymer in organic liquid, uses the oxyalkylsiloxane polymkeric substance as dispersion stabilizer.Do not provide the solvent of final composition.In the preparation process of vinyl polymer, can use radical polymerization initiator, do not mention or advise that final paint composition comprises catalyzer.
WO 01/98149 discloses a kind of curing coating composition at room temperature that comprises polysiloxane and alkoxysilyl functionalized acrylic polymers.It is packaging together that said composition can be used as so-called single packaging compositions.Yet the shortcoming of this coating composition is that it has short storage period.
The invention provides the various insufficient solutions relevant with above-mentioned prior art.Another object of the present invention provides a kind of coating composition, uses this coating composition to prepare and has the cured coating film of good integrity energy to obtain having the film of good durability.
Room-temperature-curable coating composition according to the present invention comprises:
In other words the branched polysiloxane of alkoxy-functionalization is exactly the non-linear polysiloxane of alkoxy-functionalization, and it has following formula:
Wherein each R1 independently is selected from and contains alkyl, aryl and alkoxyl group and the OSi (OR3) of 6 carbon atoms at the most
3Group, wherein each R3 has the connotation identical with R1 independently, each R2 is selected from hydrogen and contain the alkyl and the aryl of 6 carbon atoms at the most, and wherein the selection of n should to make the molecular weight of polysiloxane be that 200-is about 5000, preferred 500-2000,
Catalyzer and
Acrylic polymers.
Do not contain on acrylic polymer-based can with the polysiloxane in the coating composition or the functional group of catalyst reaction.This coating composition preferably comprises the solid that is higher than 60 weight %.
Find that coating composition of the present invention compares the storage period with prolongation with WO 01/98419 described composition.Said composition is fit to the cured film that preparation has good integrity energy and good durability.Said composition also is fit to preparation and has the coating of high gloss, and this gloss keeps very goodly under the condition of weathering and UV exposure.Based on the gross weight of base-material, the coating composition that is particularly suitable for preparing good high gloss coating preferably comprises the polysiloxane that surpasses 30 weight %.
The elongation at break of coating that uses coating composition of the present invention preparation preferably less than 20%, is more preferably less than 5% less than 100%.Use the glass transition temperature Tg of the cured film of coating composition preparation of the present invention to be higher than 0 ℃, preferably be higher than 10 ℃, more preferably be higher than 25 ℃.Using crosslinked segmental molecular weight of the coating of coating composition preparation of the present invention is less than 2000 dalton, preferably less than 1000 dalton, is more preferably less than 500 dalton, and it is desirable to less than 250 dalton.
For example can measure the second-order transition temperature (Tg) of cured coating film according to ASTM method E 1356-98, this method is to determine the standard method of test of second-order transition temperature by the dsc that is used for differential thermal analysis.For example can be according to ASTM method E 1363-97e1 calibration testing instrument, this method is the standard method of test of the temperature correction of thermodynamic analyzer.
Can pass through to use the rubber vulcanizate module of dynamic mechanics heat analysis (DMTA or DMA) commercial measurement coating and use the following relationship formula to determine crosslinked segmental molecular weight (M of coating
c):
Wherein
ρ is the density (gml of polymkeric substance
-1)
R is gas law constant (JK
-1Mol
-1)
T is temperature (K)
E ' is rubber vulcanizate module (Pa).
For example can be as Patrick K.Gallagher at Thermal Characterization ofPolymeric Materials (hotlist of polymer materials is levied), the 1st volume, Edith A.Turi version, Academic Press publishes ISBN 0-12-703783-7, and the described DMTA (DMA) that carries out of 133-149 page or leaf measures.
The volatile organic content that coating composition of the present invention preferably has (VOC) is less than the 430g/L organic solvent.More preferably, the VOC that coating composition has is less than 340g/L, in addition more preferably VOC less than 250g/L.
The gross weight of the solids content coating based composition of the present composition preferably is higher than 60 weight %, more preferably is higher than 70 weight %, even more preferably 80 weight %.
Preferred coating composition of the present invention does not contain epoxy compounds substantially, because exist epoxy compounds component and epoxy compounds can influence the weather resistance of coating with solidifying agent.For example can influence gloss and tint retention energy.After particularly in being exposed to light, the outward appearance of coated substrate can be affected.Term " is substantially devoid of epoxy compounds " and is meant the gross weight in coating composition, and coating composition comprises and is less than 0.5 weight % epoxy compounds, preferably is less than 0.1 weight % epoxide group.Coating composition most preferably of the present invention does not contain epoxy compounds fully.
The branched polysiloxane that is present in the coating composition of the present invention can comprise cyclic siloxanes ring.Group can be by these cyclic siloxanes ring branching.Polysiloxane has the average functionality greater than 2.Be that the average per molecule polysiloxane comprises more than 2 functional groups.Preferably, polysiloxane has the average functionality greater than 3.If these functional groups can react to each other and catalyzer has suitable functionality, then these functional groups can with catalyst reaction.
As mentioned above, each R1 in the polysiloxane independently is selected from and contains alkyl, aryl and alkoxyl group and the OSi (OR3) of 6 carbon atoms at the most
3Group, wherein each R3 has the connotation identical with R1 independently, and each R2 is selected from hydrogen and contains the alkyl and the aryl of 6 carbon atoms at the most.Because the volatility of every kind of pure analogue is lower, has the hydrolysis that R1 and R2 more than 6 carbon atoms tend to damage polysiloxane.The alkoxysilyl functionalized polysiloxane of preferred use.
Preferably with molecular weight for the methoxyl group of about 400-about 2000-, oxyethyl group-and the polysiloxane of silanol functional be used to prepare coating composition of the present invention.Molecular weight less than 400 methoxyl group-, oxyethyl group-and the polysiloxane of silanol functional will form crisp and the coating composition of weak shock strength will be provided.But can contain a spot of molecular weight less than 400 liquid methoxyl group-, oxyethyl group-and the polysiloxane of silanol functional.Any molecular weight surpass 400 liquid methoxyl group-, oxyethyl group-and the polysiloxane of silanol functional can use, but preferably use molecular weight less than 2000 polysiloxane, because they only can produce the composition that needs the additional solvent of (if any) seldom just can obtain application viscosity, promptly said composition can not add the solvent that surpasses existing volatile organic content (VOC) requirement and use.Usually, can not violating VOC by the high-molecular weight polysiloxane is mixed with activity or non-activated thinner requires ground to use the high-molecular weight polysiloxane.Yet this can influence film performance usually.
The suitable polysiloxane that can be used for the present composition comprises: DC 3037 and DC 3074 (all available from Dow Corning), or SY 231, SY 550 and MSE 100 (all available from Wacker).
Can by the preparation of one or more ethylenically unsaturated monomers of (being total to) polymerization be substantially devoid of can with the acrylic polymers of the functional group of polysiloxane in the coating composition or catalyst reaction.This uses polymerization starter to finish usually.The example that can (be total to) the polymeric ethylenically unsaturated monomer is that the ester of acrylic acid or the like is as (methyl) butyl acrylate, (methyl) methyl acrylate, (methyl) ethyl propenoate, (methyl) propyl acrylate, the just own ester of (methyl) vinylformic acid, (methyl) isopropyl acrylate, (methyl) butyl acrylate, methacrylic acid 2-ethylhexyl or 2-EHA, (methyl) cyclohexyl acrylate, (methyl) vinylformic acid 2,2,5-3-methyl cyclohexanol ester, (methyl) isobornyl acrylate, vinyl cyanide, methacrylonitrile, (methyl) vinylformic acid trimethoxy-silylpropyl ester and vinyl compound such as vinylbenzene, vinyl-acetic ester or vinylchlorid, wherein term (methyl) vinylformic acid is represented acrylic or methacrylic acid.
In order to prepare coating composition with low VOC, for example can be reflected at reactive thinner and have preparation acrylic polymers down by radical polymerization or any other, this reactive thinner is that the viscosity under 25 ℃ is the organic compound of 2Pas (20 pool).The preferred reactive thinner that uses has at least one for the ethylenically unsaturated monomer non-activity and can further react the functional group that forms polymer network.Find that the low viscosity polysiloxane can be used for preparing acrylic polymers.
The reactive thinner that can be used for preparing acrylic polymers comprises alkoxysilyl functionalized polysiloxane, as DC 3037 and DC 3074 (all available from Dow Corning), or SY 231, SY 550 and MSE 100 (all available from Wacker); The organoalkoxysilane monomer is as trimethoxy propyl silane, dimethoxy diphenyl silane and tetraethyl orthosilicate; And the organoalkoxysilane monomer of functional organic, as etheric acid propyl trimethoxy silicane and etheric acid propyl-triethoxysilicane.
Preferably in reactive thinner, prepare acrylic polymer by the preparaton that comprises methacrylic acid (first) ester and butyl acrylate.Optional this preparaton further comprises other ethylenically unsaturated monomer.In particularly preferred embodiments, to be polysiloxane and this polysiloxane identical with the polysiloxane that exists in the coating composition of the present invention for reactive thinner.
Determined the second-order transition temperature of gained acrylic polymers for the selection of monomer type for preparing acrylic polymers and amount of monomer.The second-order transition temperature of acrylic polymers (Tg) can be-50 ℃ to+100 ℃.The Tg of preferred acrylic polymers is 0-100 ℃, more preferably 20-80 ℃, and most preferably 30-70 ℃.
Preferably, the preparaton of preparation acrylic polymers comprises the polysiloxane of 20-80 weight % and the acrylic monomer of 80-20 weight %, the more preferably acrylic monomer of the polysiloxane of 30-80 weight % and 20-70 weight %, even the more preferably acrylic monomer of 40-70 weight % polysiloxane and 30-60 weight %, before beginning based on the polyreaction at acrylate monomer, weight % wherein comprises the total weight of the preparaton of ethylenically unsaturated monomer and polysiloxane.
Preferably, the preparaton of preparation acrylic polymers comprises the methyl methacrylate of 1-60 weight % and the butyl acrylate of 0-70 weight %, the more preferably butyl acrylate of the methyl methacrylate of 5-50 weight % and 0-60 weight %, even the more preferably methyl methacrylate of 5-40 weight % and the butyl acrylate of 0-50 weight %, before beginning based on the polyreaction at acrylate monomer, weight % wherein comprises the total weight of the preparaton of ethylenically unsaturated monomer and polysiloxane.
As implied above, preferably prepare the method for acrylic polymers by ethylenically unsaturated monomer by in the solution of reactive thinner, carrying out polyaddition reaction.Preferably carry out polymerization under the condition that has or not the sense volatile solvent being substantially free of, no official can volatile solvent be meant do not participate in ethylenically unsaturated monomer polyreaction also with the polymerization starter reaction, and can not further react the volatile solvent that forms polymer network.Perhaps can exist 10-20 weight % a small amount of as polymerization reaction mixture at the most can with the miscible no official of reactive thinner can volatile solvent.Monomeric part or all can be dissolved in the reactive thinner in advance, but preferred monomers adds in the thinner gradually with any chain-transfer agent of radical initiator and use.For example reactive thinner can be heated to 50-200 ℃, and through 12 hours at the most, preferably less than 4 hours time adding monomer, initiator and chain-transfer agent, the while kept the temperature of solution and kept 0.5-4 hour after reinforced again in reinforced process.Can in this other time, further add initiator feed to reduce the content of unreacted monomer.Yet can also remove unreacted monomer by steaming from reaction mixture and reduce its content.
Radical initiator can be for example superoxide or peroxyesters such as benzoyl peroxide, di-t-butyl peroxide, peroxidation-3,5, the 5-tri-methyl hexanoic acid tert-butyl ester, 2, two (the 2-ethyl hexanoyl peroxides)-2 of 5-, the 5-dimethylhexane or the Peroxycaprylic acid tert-butyl ester or azo-compound such as Diisopropyl azodicarboxylate or azo two (2-methylbutyronitrile).
In polymerization, can there be chain-transfer agent, as dodecyl mercaptans, butyl sulfhydryl, tetramethylolmethane four (mercaptopropionic acid ester), mercaptopropyl trimethoxysilane or dibutyl phosphite.The content of preferred control initiator and chain-transfer agent (if existence), thus make the number-average molecular weight (Mn) of resulting polymers be no more than 10000 also preferred 600-5000, and most preferably 1000-3000 can process viscosity to keep.For example, the consumption of used radical initiator (based on monomeric weight %) is generally at least 1% when not using chain-transfer agent, and preferred 2-10% perhaps can be that the initiator of 1-5% and the chain-transfer agent of 1-10% are used in combination with content.
Coating composition of the present invention also comprises catalyzer.The functional group that exists in being present in catalyzer in the curable polymeric composition and can being usually under actual condition of cure cross linking polysiloxane has active any catalyzer.This catalyzer can for example be organic or inorganic Lewis acid or alkali, preferred Lewis base.
Randomly, catalyzer is an alkoxy titanium compound, for example the titanium chelate compound as two (methyl ethyl diketone) dialkanol titanium as two (methyl ethyl diketone) diisopropanol titanium, or the alkanolamine titanate is as two (trolamine) diisopropanol titanium, or is not that the titanium alkoxide compound of inner complex is as four (sec.-propyl) titanates or tetrabutyl titanate salt.Such titanium compound that contains the alkoxyl group that is bonded on the titanium can not be as catalyzer, because titan-alkoxide functional group hydrolyzable and this catalyzer can be connected on solidified silane or the siloxanes by the Si-O-Ti key.Owing to produce higher thermostability, it can be favourable having such titanium part in cured product.Can be for example use titanium compound with the 0.1-5 weight % of base-material.The alkyl oxide of corresponding zirconium or aluminium also can be used as catalyzer.
Another kind of catalyzer is nitrate such as nitrocalcite, magnesium nitrate, aluminum nitrate, zinc nitrate or the strontium nitrate of polyvalent metal ion.The someone advises the amine curing catalysts of nitrocalcite as Resins, epoxy, but the someone advises used as the catalyzer that solidifies silane or silicone compositions as yet.We are surprised to find that when composition also contains organic amine nitrocalcite is effective catalyzer for solidify silane or siloxanes by the Si-O-Si condensation for, wherein silane or siloxanes contain at least 2 and be bonded to alkoxyl group on the silicon by the Si-O-C key.Nitrocalcite preferably uses with its four hydrated form, but also can use other hydrated form.The nitrocalcite catalyst content that needs is no more than 3 weight % of base-material usually, as 0.05-3 weight %.Use nitrocalcite catalyzer cured coating to be not easy flavescence especially being exposed to sunlight following time.
Another example of suitable catalyst is organo-tin compound such as dialkyltin dicarboxylates such as dibutyl tin laurate or dibutyltin diacetate.Such organotin catalysts for example can the coating composition base-material 0.05-3 weight % use.
In coating composition of the present invention as catalyzer effectively other compound be the organic salt such as the carboxylate salt of bismuth, three (neodecanoic acid) bismuth for example.The organic salt of other metal such as zinc, aluminium, zirconium, tin, calcium, cobalt or strontium and/or inner complex, for example methyl ethyl diketone zirconium, zinc acetate, zinc acetylacetonate, zinc octoate, stannous octoate, stannous oxalate, calcium acetylacetonate, lime acetate, 2 ethyl hexanoic acid calcium, cobalt naphthenate, calcium dodecylbenzene sulphonate or aluminum acetate also can be effective catalyzer.
Preferred catalyst is the amine of the aliphatic amine, aliphatic amine adducts, polyamidoamines, cycloaliphatic amine and cycloaliphatic amine adducts, aromatic amine, Mannich base and the ketoimine that are selected from general category, and it can be replaced by aminosilane separately wholly or in part.
Aminosilane contains at least 2, and preferred 3 are bonded to alkoxyl group on the silicon by the Si-O-C key, and contain at least 1 uncle or secondary amino group.
Preferred aminosilane has general formula Y-Si-(O-X)
3, wherein Y is H (HNR)
aAnd a is the integer of 1-6, and each R is a difunctionality organic group that independently is selected from aryl, alkyl, di alkylaryl, alkoxyalkyl and cycloalkyl, and R can change in each Y molecule.Each X can be identical or different, and be limited to and contain alkyl, hydroxyalkyl, alkoxyalkyl and the hydroxy alkoxy alkyl that is less than about 6 carbon atoms.
Preferred aminosilane for example is: aminoethyl triethoxyl silane, 3-aminopropyl triethoxysilane, N-phenyl amino propyl trimethoxy silicane, trimethoxy-silylpropyl diethylenetriamine, 3-(3-amino-benzene oxygen) propyl trimethoxy silicane, aminoethyl aminomethyl phenyl Trimethoxy silane, 2-aminoethyl 3-aminopropyl three 2-ethyl hexyl oxy silane and positive ammonia hexyl aminopropyl trimethoxysilane or its mixture.
Randomly, coating composition of the present invention comprises the lower molecular weight organoalkoxysilane with following general formula:
Wherein R3 is selected from alkyl and the cycloalkyl that contains 6 carbon atoms at the most and contains the aryl of 10 carbon atoms at the most.R4 independently is selected from and contains alkyl, alkoxyl group, hydroxyalkyl, alkoxyalkyl and the hydroxy alkoxy alkyl of 6 carbon atoms at the most.The example that can be used for the lower molecular weight organoalkoxysilane that meets following formula of coating composition is the dimethoxy diphenyl silane.
The gross weight of the amount coating based composition of this lower molecular weight organoalkoxysilane in coating composition is preferably 5-20 weight %, more preferably from about 10 weight %.
Randomly, this coating composition comprise have can with the acrylic polymers of the functional group of polysiloxane in the coating composition or catalyst reaction.The example of this acrylic polymers is the alkoxysilyl functionalized acrylic polymers that for example is described among the WO 01/98419.Another example is for example to be described in the acrylic polymers of the epoxy-functional among the WO 01/51575 such as the acrylic polymers of glycidyl-functionalised.Such acrylic polymers can obtain by the polyreaction in reactive thinner.Preferred reactive thinner is a polysiloxane, and the polysiloxane that exists in this polysiloxane and the coating composition of the present invention is identical.Have can with this acrylic polymers of the functional group of polysiloxane in the coating composition or catalyst reaction preferably be substantially devoid of and can prepare respectively with the acrylic polymers of the functional group of polysiloxane in the coating composition or catalyst reaction.This be for fear of final formation only comprise have can with the composition of the silicone copolymers of the functional group of polysiloxane or catalyst reaction.
Coating composition of the present invention can comprise one or more other compositions.Therefore they can contain one or more pigment, as titanium dioxide (white pigment), coloured pigment such as yellow or red iron oxide pigment or phthalocyanine pigment and/or one or more reinforcing pigments such as mica ferric oxide or crystalline silica and/or one or more corrosion-inhibiting pigments such as metallic zinc, zinc phosphate, wollastonite or chromic salt, molybdate or phosphonate and/or filler pigments such as barite, talcum or lime carbonate.Said composition can contain thickening material such as particulate silicon-dioxide, wilkinite, hydrogenated castor oil or polyamide wax.Said composition can also contain softening agent, pigment dispersing agent, stablizer, glidant or diluting solvent.
Coating composition of the present invention solidifies under the temperature of room temperature such as 5-30 ℃ usually, and thereby be fit to be applied to be heating and curing infeasible than on the macrostructure body.Coating composition perhaps of the present invention can solidify down quickening the temperature that raises such as 30-50 ℃ to the highest 100 ℃ or 130 ℃ and solidify.Depend on the moisture of existence with the hydrolysis of silicon bonded alkoxy group; Atmospheric moisture all is enough under nearly all weather, but when in the temperature-curable that raises or when solidifying in the place of humidity very low (desert), may need to add the moisture of controlled quatity in coating.Preferably water is separated packing with any compound or polymkeric substance that contains silicon bonding alkoxyl group.
Coating composition of the present invention can be used as finishing paint and/or priming paint usually.The coating composition that contains the higher proportion polysiloxane has high gloss, and this gloss keeps finely under the condition of weathering and UV exposure.Before being particularly suitable for being coated in and being coated with, they are exposed to the base material under weather condition such as the sunlight for a long time.Though in coating composition of the present invention, generally do not require the use solvent, and coating composition of the present invention can be the low-down not solvent-laden coating of measuring of volatile organic content, if but coating composition comprises organic solvent (thinner) as dimethylbenzene then can obtain the gloss of top.Coating composition can contain alcohol as ethanol or butanols to extend shelf life and to control the solidified commencing speed.
Finishing paint according to the present invention can be applicable on the various priming paint, for example the organic priming paint such as the epoxy resin primer of inorganic zinc silicate or organic rich zinc silicate priming paint and containing metal zinc, resistant metal sheet or isolation pigment.Coating composition of the present invention has good especially bonding effect and does not need intermediary connecting layer or mist coating the inorganic silicic acid spelter coating.Finishing paint composition of the present invention can also be applied directly on " metallikon " coating of aluminium or zinc or galvanized steel, stainless steel, aluminium or frosting such as the glass fiber-reinforced polyester or polyester gel coating.This coating composition can for example be used as the finishing paint on buildings, steel structure body, automobile, aircraft and other vehicles and the general industrial machine and equipment.This finishing paint can be add the coating of pigment or be particularly useful for automobile or yacht on transparent (not adding pigment) coating.This coating composition can directly be applied on the carbon steel of preparation as priming paint/finishing paint.
Coating composition perhaps of the present invention can be used as the protectiveness priming paint on steel surface particularly such as bridge, pipeline, industrial equipments or buildings, oil and gas apparatus or the ship.Usually with anti-corrosion paint it is painted for this reason.For example can use the zinc powder colouring; Coating of the present invention has the antiseptic property similar to known zinc silicate coating and more difficult generation opening crack and be easy to carry out cover with polysiloxane finishing paint such as finishing paint of the present invention especially and apply.Paint base composition of the present invention can be as imperfect surface as aging and ruined steel or " ginger steel " (destroyed and begin to produce the steel of little rust staining), the weathering steel of artificial preparation and the maintenance and the repair paint of aging coating.
The component of preferred coating composition of the present invention is packaging together as so-called single packaging compositions.It is favourable only having a spot of moisture in said composition.
With reference to the following example the present invention is described clearly.These embodiment are intended to the present invention is described and do not should be understood to limit the scope of the invention by any way.
In an embodiment, pbw is meant weight part.
Embodiment
Embodiment 1 (preparation of acrylic polymer)
In the polysiloxane solvent mixture, prepare acrylic polymers.For the unsaturated starting monomer of the olefinic of acrylic polymers, employed polysiloxane DC3074 available from Dow Corning does not have reactivity basically.
Alkoxysilyl functionalized polyorganosiloxane resin DC 3074 and solvent Three methyl Benzene (TMB) adding are equipped with in the reaction flask of agitator, condenser, introducing nitrogen device, thermopair and feed port.Under nitrogen atmosphere, temperature is elevated to 140 ℃.
Monomers methyl methacrylate (MMA) and butyl acrylate (BA) and initiator tert-butyl peroxide (TBPO) were added through 2 hours, make temperature of reaction keep constant down simultaneously at 140 ℃.After reinforced finishing, reaction mixture kept 1 hour down at 140 ℃, and then further added initiator (about TBPO initial content 10%).Temperature kept under 140 ℃ 2 hours again.Then with reaction mixture cool to room temperature and discharging.
5 kinds of acrylic polymers have been prepared according to the method.In the preparation process of 3 kinds of these polymkeric substance, in reaction mixture, added chain-transfer agent uncle dodecyl mercaptans (TDT).
Table 1
| The polymkeric substance numbering | Polysiloxane 1 pbw | TMB 2 pbw | MMA 3 pbw | BA 4 pbw | TBPO 5 pbw | TDT 6 pbw |
| 1 | 400.0 | 50.0 | 75.0 | 25.0 | 5.5 | - |
| 2 | 300.0 | 50.0 | 50.0 | 150.0 | 9.8 | - |
| 3 | 300.0 | 50.0 | 50.0 | 150.0 | 9.8 | 3.6 |
| 4 | 325.0 | 50.0 | 150.0 | 25.0 | 9.9 | 3.4 |
| 5 | 400.0 | 50.0 | 75.0 | 25.0 | 5.5 | 1.9 |
1) available from the DC 3074 of Dow Corning
2) Three methyl Benzene
3) methyl methacrylate
4) butyl acrylate
5) tert-butyl peroxide
6) uncle's dodecyl mercaptans
Embodiment 2 (preparation of coating composition)
Use the acrylic polymers of embodiment 1 preparation and the mixture of polysiloxane to prepare coating composition.Use aminopropyl triethoxysilane (APTES), Three methyl Benzene (TMB) and tetraethyl orthosilicate (TEOS) the preparation coating composition of different amounts.The prescription of coating composition is shown in Table 2.
Table 2
| Component | pbw |
| Polymkeric substance 1 | 115.8 |
| Titanium dioxide 2 | 56.2 |
| Alcohol 3 | 4.0 |
| Defoamer 4 | 1.0 |
| Disparlon 5 | 2.0 |
| APTES 6 | 0.0-14.0 |
| TMB 7 | 0.0-14.0 |
| TEOS 8 | 0.0-14.0 |
1) in embodiment 1 preparation polymeric blends, in polysiloxane, comprise acrylic polymers
2) available from the Kronos 2063 of Kronos
3) Virahol
4) available from the Byk 80 of Byk-Chemie
5) available from the Disparlon 6650 of Kusumoto Chemicals
6) aminopropyl triethoxysilane
7) Three methyl Benzene
8) tetraethyl orthosilicate
Coating composition according to formulation shown in the table 2 is listed in the table 3.
Table 3
| The coating composition numbering | The polymkeric substance numbering 1 | APTES 2 pbw | TMB 3 pbw | TEOS 4 pbw |
| 1A | 1 | 14.0 | 14.0 | - |
| 1B-I | 2 | 7.0 | - | 14.0 |
| 1B-II | 2 | 14.0 | 14.0 | - |
| 1C | 3 | 7.0 | 14.0 | - |
| 1D | 4 | 14.0 | - | 14.0 |
| | 5 | 7.0 | 14.0 | - |
1) in embodiment 1 preparation polymeric blends, in polysiloxane, comprise acrylic polymers
2) aminopropyl triethoxysilane
3) Three methyl Benzene
4) tetraethyl orthosilicate
Embodiment 3 (test of coating composition)
Measure the viscosity of the uncured coating composition of embodiment 2.Then, use and cure coating compositions.Measuring coating in the environment with differing temps and humidity becomes to refer to touch and does the needed time and become the time that spends before doing something in disregard of obstacles at coating.After curing, the hardness and the gloss of test gained coating.
The result of all tests is listed among table 4a and the 4b.
Table 4a
| The coating composition numbering | Viscosity 1 | Refer to touch dried 2 (10/80) | Refer to touch dried 3 (25/50) | Do something in disregard of obstacles 4 (25/50) |
| Pool (25 ℃) | Minute | Minute | Minute | |
| 1A | 2.24 | 340 | 145 | 350 |
| 1B-I | 5.09 | 1235 | 630 | 1500 |
| 1B-II | 3.61 | 675 | 240 | 625 |
| 1C | 3.79 | 1500 | 920 | 1500 |
| 1D | 2.6 | 1500 | 370 | 1010 |
| 1E | 2.21 | 1500 | 925 | 1500 |
1) 25 ℃ of viscosity of measuring down, the unit pool
2) set to touch time under 10 ℃ and 80% relative humidity, unit minute
3) set to touch time under 25 ℃ and 50% relative humidity, unit minute
4) dry-hard time under 25 ℃ and 50% relative humidity, unit minute
Table 4b
| The coating composition numbering | K nig hardness 1 (10/80) | K nig hardness 2 (25/50) | K nig hardness 3 (40/25) | Gloss 4 |
| 1A | 45 | 103 | 78 | 77 |
| 1B-I | 7 | 13 | 4 | 62 |
| 1B-II | 12 | 26 | 19 | 84 |
| 1C | 4 | 9 | 3 | 36 |
| 1D | 24 | 24 | 15 | 47 |
| 1E | 57 | 57 | 11 | 65 |
1) K nig hardness under 10 ℃ and 80% relative humidity after 7 days
2) K nig hardness under 25 ℃ and 50% relative humidity after 7 days
3) K nig hardness under 40 ℃ and 25% relative humidity after 7 days
4) gloss measured according to ASTM D523
Embodiment 4 (preparation of acrylic polymer)
In the polysiloxane solvent mixture, prepare acrylic polymers.For the unsaturated starting monomer of the olefinic of acrylic polymers, employed polysiloxane DC3074 available from Dow Corning be basically do not have reactive.
Alkoxysilyl functionalized polyorganosiloxane resin DC 3074 and solvent Three methyl Benzene (TMB) adding are equipped with in the reaction flask of agitator, condenser, introducing nitrogen device, thermopair and feed port.Under nitrogen atmosphere, temperature is elevated to 140 ℃.
Monomers methyl methacrylate (MMA), butyl acrylate (BA) and (choosing wantonly) methacrylic acid trimethoxy-silylpropyl ester (TMSPMA) and initiator tert-butyl peroxide (TBPO) were added through 2 hours, make temperature of reaction keep constant down simultaneously at 140 ℃.After reinforced finishing, reaction mixture kept 1 hour down at 140 ℃, and then further added initiator (about TBPO initial content 10%).Temperature kept under 140 ℃ 2 hours again.Then with reaction mixture cool to room temperature and discharging.
2 kinds of polymkeric substance have been prepared according to the method.In the process of preparation acrylic polymer, No. 7 methacrylic acid trimethoxy-silylpropyl ester (TMSPMA) added in the reaction mixture, obtain alkoxysilyl functionalized acrylic polymers.
Table 5
| The polymkeric substance numbering | Polysiloxane pbw | TMB 2 pbw | MMA 3 pbw | BA 4 pbw | TBPO 5 pbw | TMSPMA 6 pbw |
| 6 | 300.0 | 50.0 | 100.0 | 100.0 | 10.75 | - |
| 7 | 300.0 | 50.0 | 87.5 | 87.5 | 10.0 | 25.0 |
1) available from the DC 3074 of Dow Corning
2) Three methyl Benzene
3) methyl methacrylate
4) butyl acrylate
5) tert-butyl peroxide
6) methacrylic acid trimethoxy-silylpropyl ester
Embodiment 5 (preparation of coating composition)
Use the acrylic polymers of preparation among the embodiment 4 and the mixture of polysiloxane to prepare coating composition.The prescription of coating composition is shown in Table 6.
Table 6
| Component | pbw |
| Polymkeric substance 1 | 165.0 |
| Titanium dioxide 2 | 80.0 |
| Disparlon 3 | 1.65 |
| APTES 4 | 10.0 |
| TEOS 5 | 20.0 |
1) in embodiment 4 preparation polymeric blends, in polysiloxane, comprise acrylic polymers
2) available from the Kronos 2063 of Kronos
3) available from the Disparlon 6650 of Kusumoto Chemicals
4) aminopropyl triethoxysilane
5) tetraethyl orthosilicate
According to the coating composition of formulation shown in the table 6 4A (comprising polymkeric substance No. 6) and coating composition 4B (comprising polymkeric substance No. 7), and 40 ℃ of storages down.
Embodiment 6 (coating composition test)
The viscosity that changes with the storage time of measuring coating composition of the present invention and be coating composition 4A raises, described composition 4A comprise polysiloxane, catalyzer and be substantially devoid of can with the acrylic polymers of the functional group of polysiloxane in the coating composition or catalyst reaction.The viscosity rising that changes with the storage time of these data and coating composition 4B compares, described composition 4B comprises polysiloxane, catalyzer and alkoxysilyl functionalized acrylic polymers, and be not substantially devoid of can with the acrylic polymers of the functional group of polysiloxane in the coating composition or catalyst reaction.
Time dependent viscosity raises and is listed in the table below.
| Fate | Coating composition numbering 4A | Coating |
| 0 | 11.5 | 21.8 |
| 3 | 11.9 | 23.7 |
| 6 | 11.9 | 23.9 |
| 10 | 12.2 | 25.2 |
| 16 | 12.3 | 26.2 |
| 34 | 12.9 | 28.4 |
| 84 | 13.8 | 31.1 |
Coating composition 4A demonstrates slower viscosity than coating composition 4B and raises.This shows scheming in Fig. 1.
Claims (16)
1. room-temperature-curable coating composition, said composition comprises:
-have a branched polysiloxane of the alkoxy-functionalization of following formula:
Wherein each R1 is independently selected from and contains alkyl, aryl and alkoxyl group and the OSi (OR3) of 6 carbon atoms at the most
3Group, wherein each R3 is independently selected from and contains alkyl, aryl and the alkoxyl group of 6 carbon atoms at the most, each R2 is selected from hydrogen and contain the alkyl and the aryl of 6 carbon atoms at the most, and wherein the selection of n should to make the molecular weight of polysiloxane be 200-5000,
The catalyzer of-aminofunctional and
-acrylic polymers, do not contain on this acrylic polymer-based can with the polysiloxane in the coating composition or the functional group of catalyst reaction,
Wherein said coating composition comprises the solid that is higher than 60 weight %.
2. according to the coating composition of claim 1, it is characterized in that obtaining acrylic polymers by polymerization in polysiloxane.
3. according to the coating composition of claim 1, it is characterized in that polysiloxane is alkoxysilyl functionalized polysiloxane.
4. according to the coating composition of claim 2, it is characterized in that polysiloxane is alkoxysilyl functionalized polysiloxane.
5. according to 1 coating composition, it is characterized in that catalyzer is an aminosilane.
6. according to 2 coating composition, it is characterized in that catalyzer is an aminosilane.
7. according to 3 coating composition, it is characterized in that catalyzer is an aminosilane.
8. according to 4 coating composition, it is characterized in that catalyzer is an aminosilane.
9. according to each coating composition among the claim 1-8, it is characterized in that acrylic polymers has 0-100 ℃ second-order transition temperature.
10. according to each coating composition among the claim 1-8, it is characterized in that acrylic monomer by polymerization 20-80 weight % in the polysiloxane of 80-20 weight %, add catalyzer then and obtain coating composition, wherein based on the gross weight of ethylenically unsaturated monomer before beginning polyreaction at acrylic ester monomer and polysiloxane and calculated weight %.
11. coating composition according to claim 9, it is characterized in that acrylic monomer by polymerization 20-80 weight % in the polysiloxane of 80-20 weight %, add catalyzer then and obtain coating composition, wherein based on the gross weight of ethylenically unsaturated monomer before beginning polyreaction at acrylic ester monomer and polysiloxane and calculated weight %.
12. coating composition according to claim 10, it is characterized in that by the methyl methacrylate of polymerization 1-60 weight % in the polysiloxane of 20-80 weight % and the butyl methacrylate of 0-70 weight %, add catalyzer then and obtain coating composition, wherein based on the gross weight of ethylenically unsaturated monomer before beginning polyreaction at acrylic ester monomer and polysiloxane and calculated weight %.
13. coating composition according to claim 11, it is characterized in that by the methyl methacrylate of polymerization 1-60 weight % in the polysiloxane of 20-80 weight % and the butyl methacrylate of 0-70 weight %, add catalyzer then and obtain coating composition, wherein based on the gross weight of ethylenically unsaturated monomer before beginning polyreaction at acrylic ester monomer and polysiloxane and calculated weight %.
14. according to each coating composition among the claim 1-13 as the purposes of protective coating.
15. at room temperature apply purposes in the large structure according to each coating composition among the claim 1-13.
16. at room temperature apply purposes in ship, bridge, buildings, industrial equipments or the oil rig according to each coating composition among the claim 1-13.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03250594 | 2003-01-30 | ||
| EP03250594.3 | 2003-01-30 | ||
| US60/456,284 | 2003-03-20 |
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| CN1745152A CN1745152A (en) | 2006-03-08 |
| CN100338161C true CN100338161C (en) | 2007-09-19 |
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| CNB2004800031983A Expired - Lifetime CN100338161C (en) | 2003-01-30 | 2004-01-26 | Ambient temperature curing coating composition |
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| JP (1) | JP4773949B2 (en) |
| CN (1) | CN100338161C (en) |
| ZA (1) | ZA200506915B (en) |
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| KR100954482B1 (en) * | 2005-04-05 | 2010-04-22 | 주고꾸 도료 가부시키가이샤 | Tie coat for organopolysiloxane antifouling coat, composite coats, and ships and underwater structures covered with the composite coats |
| CA2636078C (en) * | 2006-01-02 | 2014-07-08 | Akzo Nobel Coatings International B.V. | Heat resistant coating |
| KR101183892B1 (en) * | 2010-02-01 | 2012-09-19 | 주식회사 케이씨씨 | One-component type, room-temperature curing and water-soluble top coating composition |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4138387A (en) * | 1973-12-26 | 1979-02-06 | General Electric Company | Poly(olefinic monomer) filled-poly(organosiloxane) compositions |
| US4965312A (en) * | 1985-11-01 | 1990-10-23 | Kansai Paint Company, Limited | Nonaqueous vehicle composition for coating materials |
| US5530063A (en) * | 1993-06-15 | 1996-06-25 | Shin-Etsu Chemical Co., Ltd. | Room temperature curable organopolysiloxane composition |
| CN1204553A (en) * | 1997-07-09 | 1999-01-13 | 北美埃尔夫爱托化学股份有限公司 | Organotin sulfonate catalysts and their manufacture method |
| WO1999031179A1 (en) * | 1997-12-18 | 1999-06-24 | The B.F. Goodrich Company | A polysiloxane having a copolymer dispersed therein and sealants containing the same |
| EP1063270A2 (en) * | 1999-06-21 | 2000-12-27 | General Electric Company | Adhesion primer for use with RTV silicones |
| WO2001051575A1 (en) * | 2000-01-12 | 2001-07-19 | International Coatings Ltd. | Ambient temperature curing coating composition |
| WO2001098419A1 (en) * | 2000-06-23 | 2001-12-27 | International Coatings Limited | Ambient temperature curing coating composition |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5275645A (en) * | 1992-11-24 | 1994-01-04 | Ameron, Inc. | Polysiloxane coating |
| JPH1095949A (en) * | 1996-09-20 | 1998-04-14 | Nippon Synthetic Chem Ind Co Ltd:The | Pigment-dispersing type resin composition and coating using the same |
-
2004
- 2004-01-26 CN CNB2004800031983A patent/CN100338161C/en not_active Expired - Lifetime
- 2004-01-26 JP JP2006501612A patent/JP4773949B2/en not_active Expired - Fee Related
-
2005
- 2005-08-29 ZA ZA200506915A patent/ZA200506915B/en unknown
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4138387A (en) * | 1973-12-26 | 1979-02-06 | General Electric Company | Poly(olefinic monomer) filled-poly(organosiloxane) compositions |
| US4965312A (en) * | 1985-11-01 | 1990-10-23 | Kansai Paint Company, Limited | Nonaqueous vehicle composition for coating materials |
| US5530063A (en) * | 1993-06-15 | 1996-06-25 | Shin-Etsu Chemical Co., Ltd. | Room temperature curable organopolysiloxane composition |
| CN1204553A (en) * | 1997-07-09 | 1999-01-13 | 北美埃尔夫爱托化学股份有限公司 | Organotin sulfonate catalysts and their manufacture method |
| WO1999031179A1 (en) * | 1997-12-18 | 1999-06-24 | The B.F. Goodrich Company | A polysiloxane having a copolymer dispersed therein and sealants containing the same |
| EP1063270A2 (en) * | 1999-06-21 | 2000-12-27 | General Electric Company | Adhesion primer for use with RTV silicones |
| WO2001051575A1 (en) * | 2000-01-12 | 2001-07-19 | International Coatings Ltd. | Ambient temperature curing coating composition |
| WO2001098419A1 (en) * | 2000-06-23 | 2001-12-27 | International Coatings Limited | Ambient temperature curing coating composition |
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| JP2006516664A (en) | 2006-07-06 |
| JP4773949B2 (en) | 2011-09-14 |
| ZA200506915B (en) | 2006-11-29 |
| CN1745152A (en) | 2006-03-08 |
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