CA2509837A1 - Coating composition - Google Patents

Coating composition Download PDF

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Publication number
CA2509837A1
CA2509837A1 CA002509837A CA2509837A CA2509837A1 CA 2509837 A1 CA2509837 A1 CA 2509837A1 CA 002509837 A CA002509837 A CA 002509837A CA 2509837 A CA2509837 A CA 2509837A CA 2509837 A1 CA2509837 A1 CA 2509837A1
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CA
Canada
Prior art keywords
coating composition
group
functional
polymer
multifunctional
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.)
Granted
Application number
CA002509837A
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French (fr)
Other versions
CA2509837C (en
Inventor
Jyotindra K. Doshi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Swimc LLC
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Individual
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Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2509837A1 publication Critical patent/CA2509837A1/en
Application granted granted Critical
Publication of CA2509837C publication Critical patent/CA2509837C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
    • C08G18/4269—Lactones
    • C08G18/4277—Caprolactone and/or substituted caprolactone
    • 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
    • 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
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2312/00—Crosslinking
    • C08L2312/08—Crosslinking by silane
    • 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
    • C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups

Abstract

A coating composition comprising a reaction product of the following components: (a) at least one cyclic ether or anhydride; and (b) an alkoxysilane-functional polyacrylate, alkyd, polyester, epoxy, or a multifunctional polyol; and (c) at least one metal ester having the general formula Rm-M(OR~)n, in which M is Si, Al, Zr, or Ti, Mg, B, W. or Mo R is a hydrocarbon group of less than 10 carbon atoms or a group comprising hydroge n, carbon and oxygen of less than 20 carbon atoms, R~ is an alkyl or aryl group with less than 10 carbon atoms, m has values of 0, 1, 2 an 3 and correspondingly n is 4, 3, 2, or 1; and (d) at least one organofunctional alkoxysilane.

Claims (18)

1. A coating composition comprising the reaction product of the following components:

(a) at least one cyclic ether or anhydride; and (b) an alkoxysilane-functional polyacrylate, alkyd, polyester, epoxy or a multifunctional polyol; and (c) at least one metal ester having the general formula Rm-M(OR')n, wherein M is Si, Al, Zr, Ti, Mg, B, W or Mo, and where Rm is a hydrocarbon group of less than 10 carbon atoms or a group comprising hydrogen, carbon and oxygen of less than 20 carbon atoms, R' is an alkyl or aryl group of less than 10 carbon atoms, m has values of 0, 1, 2 an 3 and correspondingly n is 4, 3, 2, or 1; and (d) at least one organofunctional alkoxysilane that is compatible with the metal ester.
2. The coating composition of claim 1, further comprising the reaction product of a multifunctional polyol and an isocyanate-functional silane.
3. The coating composition of claim 1, further comprising the reaction product of a multifunctional polyol and a multi functional orthosilicate.
4. The coating composition of claim 1, further comprising the reaction product of a multifunctional polyol and a metal ester.
5. The coating composition of claim 1, wherein the cyclic ether is selected from the group consisting of cycloaliphatic epoxide, cycloaliphatic diepoxide, multifunctional glycidyl epoxide or multifunctional glycidyl diepoxide, epoxidized oil, and polymers containing an oxirane ring.
6. The coating composition of claim 1, wherein the cyclic ether is a multifunctional glycidyl, aliphatic, or cycloaliphatic epoxide.
7. The coating composition of claim 1, wherein the cyclic ether is an epoxidized oil or a polymer containing an oxirane ring.
8. The coating composition of claim 1, further comprising a hydroxy-functional polymer.
9. The coating composition of claim 1, further comprising a silicone hydride functional polymer.
10. The coating composition of claim 9, wherein the silicone hydride is polyhydidomethylsiloxane.
11. The coating composition of claim 1, further comprising a compound having primary, secondary or tertiary amine functionality.
12. The coating composition of claim 1, further comprising an alpha,beta unsaturated polymer.
13. The coating composition of claim 12, wherein the alpha,beta unsaturated polymer is selected from the group consisting of acrylate-functional silanes, methacrylate-functional silanes, acrylic urethane, and acrylated urethane silanes.
14. The coating composition of claim 1, wherein the alkoxysilane-functional polyacrylate is represented by the formula:

[R1] n -C - C [R2] -Si - [OR3]3 wherein R1 is an organic acrylic polymer, R2 is a divalent organic radical, and R3 is a monovalent radical that can include heteroatoms (e.g., oxygen, nitrogen, sulfur), including but not limited to, alkyl (linear or branched), cycloalkyl, aryl, allyl, or aralkyl, and wherein the silicon alkoxide functionality is pendant in the acrylic polymer available for further crosslinking.
15. The coating composition of claim 1, wherein the organofunctional alkoxysilane is selected from the group consisting of beta-(3,4-epoxycyclohexyl) ethyltrimethoxysilane;
gamma-glycidoxypropyltrimethoxy; vinyltriethoxysilane; vinyltris (2-methoxyethoxy) silane ; gamma-methacryloxy-propyltrimethoxy silane; and vinyltriacetoxy silane.
16. The coating composition of claim 1, wherein the metal ester is selected from the group consisting of tetra-isopropyl titanate; tetra-n-butyl titanate; tetra-n-butyl zirconate, tetraethyl titanate, tetraethyl zirconate, tetra 2-ethylhexyl titanate, aluminumisopropoxide, aluminum n-butoxide, aluminum- s-butoxide, orthosilicate, tetraethylorthosilicate, and tetraisopropyl zirconate.
17. The coating composition of claim 1, further comprising an alkyd, polyester, or polyamine, polyamide, polyepoxide, or any other single or multi functional hydroxyl group containing compound.
18. The coating composition of claim 1, further comprising a silicate-, ortho-silicate-, or silicone alkoxide containing monomers, oligomers or polymers.
CA2509837A 2002-12-20 2003-12-19 Coating composition Expired - Fee Related CA2509837C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US43584002P 2002-12-20 2002-12-20
US60/435,840 2002-12-20
PCT/US2003/040819 WO2004058907A1 (en) 2002-12-20 2003-12-19 Coating composition

Publications (2)

Publication Number Publication Date
CA2509837A1 true CA2509837A1 (en) 2004-07-15
CA2509837C CA2509837C (en) 2010-10-19

Family

ID=32682283

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2509837A Expired - Fee Related CA2509837C (en) 2002-12-20 2003-12-19 Coating composition

Country Status (9)

Country Link
US (1) US7399352B2 (en)
EP (1) EP1585795B1 (en)
CN (1) CN1729261A (en)
AU (1) AU2003297440A1 (en)
BR (1) BR0316867B1 (en)
CA (1) CA2509837C (en)
DE (1) DE60319277T2 (en)
MX (1) MXPA05006553A (en)
WO (1) WO2004058907A1 (en)

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DE102004052420A1 (en) * 2004-10-28 2006-05-04 Wacker Chemie Ag Chromate-free preparation for anti-corrosive coatings on metals
US7435777B2 (en) * 2005-12-30 2008-10-14 Columbia Insurance Company Low-VOC compositions containing a polymeric latex, coatings made therefrom, substrates containing same, and methods for making same
KR101249090B1 (en) * 2006-11-14 2013-03-29 삼성전자주식회사 Composition for Preparing Organic Insulator and the Organic Insulator prepared by using the same
KR20130008630A (en) 2007-08-09 2013-01-22 아크조노벨코팅스인터내셔널비.브이. High solids epoxy coating composition
US9540479B2 (en) * 2009-12-29 2017-01-10 3M Innovative Properties Company Polyurethane nanocomposites
JP5963607B2 (en) * 2012-08-10 2016-08-03 石塚硝子株式会社 Organic inorganic adhesive composition
WO2014106552A1 (en) * 2013-01-03 2014-07-10 Basf Coatings Gmbh One -component, curable coating composition, processes for making and using them, and coatings and articles prepared with them
EP3687831A1 (en) * 2017-09-26 2020-08-05 Avery Dennison Retail Information Services, LLC Heat transfer label
JP7366674B2 (en) 2019-09-25 2023-10-23 ベック株式会社 Covering material

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Also Published As

Publication number Publication date
CA2509837C (en) 2010-10-19
AU2003297440A1 (en) 2004-07-22
DE60319277T2 (en) 2009-02-12
US7399352B2 (en) 2008-07-15
BR0316867A (en) 2005-10-18
CN1729261A (en) 2006-02-01
EP1585795B1 (en) 2008-02-20
WO2004058907A1 (en) 2004-07-15
EP1585795A1 (en) 2005-10-19
DE60319277D1 (en) 2008-04-03
US20040210022A1 (en) 2004-10-21
MXPA05006553A (en) 2005-08-16
BR0316867B1 (en) 2014-04-29

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Effective date: 20210831

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