CA2477296A1 - Polymerization of a reactive diluent in the presence of an epoxy-amine material, and coating compositions prepared thereby - Google Patents

Polymerization of a reactive diluent in the presence of an epoxy-amine material, and coating compositions prepared thereby Download PDF

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Publication number
CA2477296A1
CA2477296A1 CA002477296A CA2477296A CA2477296A1 CA 2477296 A1 CA2477296 A1 CA 2477296A1 CA 002477296 A CA002477296 A CA 002477296A CA 2477296 A CA2477296 A CA 2477296A CA 2477296 A1 CA2477296 A1 CA 2477296A1
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CA
Canada
Prior art keywords
coating composition
composition
reactive diluent
epoxy
aqueous dispersion
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
CA002477296A
Other languages
French (fr)
Other versions
CA2477296C (en
Inventor
Martin Peter Joseph Heuts
Lonnie Steven Jones
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.)
Sherwin Williams Co
Original Assignee
Valspar Sourcing, Inc.
Martin Peter Joseph Heuts
Lonnie Steven Jones
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Valspar Sourcing, Inc., Martin Peter Joseph Heuts, Lonnie Steven Jones filed Critical Valspar Sourcing, Inc.
Publication of CA2477296A1 publication Critical patent/CA2477296A1/en
Application granted granted Critical
Publication of CA2477296C publication Critical patent/CA2477296C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • 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
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
    • 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
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • 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
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/04—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polycarbonamides, polyesteramides or polyimides
    • 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
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/10—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers containing more than one epoxy radical per molecule
    • 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
    • C08G18/58—Epoxy resins
    • C08G18/584—Epoxy resins having nitrogen
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/182—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents
    • C08G59/184—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents with amines
    • 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
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • 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
    • 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
    • C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
    • C09D179/02—Polyamines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
    • C09D5/4473—Mixture of polymers
    • 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
    • C08G2270/00—Compositions for creating interpenetrating networks
    • 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
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/10—Homopolymers or copolymers of methacrylic acid esters
    • C08L33/12—Homopolymers or copolymers of methyl methacrylate

Abstract

A process including the polymerization of a reactive diluent, which is prese nt in an aqueous dispersion that further includes an epoxy-amine material, is disclosed. The resulting composition is useful as a coating composition.</SD OAB>

Claims (29)

1. A method of preparing a coating composition, comprising the steps of:
making an aqueous dispersion of a composition comprising an advanced molecular weight epoxy-amine material and a reactive diluent; and polymerizing the reactive diluent to provide the coating composition.
2. The method of claim 1, further comprising the step of:
combining an amine and an epoxy material in the presence of a reactive diluent to provide the composition comprising an advanced molecular weight epoxy-amine material and a reactive diluent.
3. The method of claim 1, wherein the step of making the aqueous dispersion comprises combining the composition with an acid.
4. The method of claim 2, wherein the epoxy material is derived from Bisphenol A and epichlorihydrin.
5. The method of claim 2, wherein the epoxy material is dissolved or dispersed in the reactive diluent.
6. The method of claim 1, wherein the epoxy-amine material has residual epoxy functionality.
7. The method of claim 6, further comprising the step of:
reacting the epoxy-amine material having residual epoxy functionality with an active hydrogen compound or precursor.
8. The method of claim 7, wherein the step of reacting is carried out before the step of making the aqueous dispersion.
9. The method of claim 7, wherein the step of reacting is carried out after the step of making the aqueous dispersion.
10. The method of claim 7, wherein the step of reacting is carried out after the step of polymerizing the reactive diluent.
11. The method of claim 1, wherein the coating composition further comprises a crosslinker.
12. The method of claim 1, wherein the aqueous dispersion further comprises a surfactant.
13. The method of claim 3, wherein the composition is combined with a surfactant before combining the composition with the acid.
14. The method of claim 3, wherein the acid is an aqueous acid.
15. The method of claim 1, wherein the step of making the aqueous dispersion comprises:
combining the composition with an acid to provide an acidified composition; and combining the acidified composition with an aqueous liquid.
16. The method of claim 15, wherein the aqueous liquid further comprises a surfactant.
17. The method of claim 1, wherein the reactive diluent comprises a multifunctional material.
18. The method of claim 1, further comprising the step of:
adding an additional reactive diluent before the polymerizing step.
19. The method of claim 1, wherein the reactive diluent is polymerized by free radical polymerization.
20. The method of claim 1, wherein the coating composition further comprises a solvent.
21. The method of claim 1, wherein the coating composition is a packaging coating composition, an anticorrosive coating composition, a stain blocker coating composition, a paper coating composition, a cement board coating composition, a fiberboard coating composition, and combinations thereof.
22. The method of claim 1, wherein the coating composition is substantially free of solvent.
23. The method of claim 1, wherein the coating composition has a volatile organic compound content of at most 0.2 kilograms per liter of solids.
24. The method of claim 3, wherein the coating composition has a volatile organic compound content, excluding acid, of at most 0.2 kilograms per liter of solids.
25. A coating composition prepared according to the method of claim 1.
26. A method of coating an article comprising the steps of:
applying a coating composition prepared according to the method of claim 1 to an article; and hardening the coating composition to provide a coated article.
27. The method of claim 26, wherein the coating composition further comprises a crosslinker.
28. The method of claim 26, further comprising the step of heating the coated article to provide a crosslinked coating.
29. The method of claim 26, wherein the step of applying comprises applying the coating composition by an electro coat process.
CA002477296A 2002-03-08 2003-03-07 Polymerization of a reactive diluent in the presence of an epoxy-amine material, and coating compositions prepared thereby Expired - Fee Related CA2477296C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US36260802P 2002-03-08 2002-03-08
US60/362,608 2002-03-08
PCT/US2003/006969 WO2003076536A1 (en) 2002-03-08 2003-03-07 Polymerization of a reactive diluent in the presence of an epoxy-amine material, and coating compositions prepared thereby

Publications (2)

Publication Number Publication Date
CA2477296A1 true CA2477296A1 (en) 2003-09-18
CA2477296C CA2477296C (en) 2009-12-22

Family

ID=27805202

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002477296A Expired - Fee Related CA2477296C (en) 2002-03-08 2003-03-07 Polymerization of a reactive diluent in the presence of an epoxy-amine material, and coating compositions prepared thereby

Country Status (13)

Country Link
US (3) US20050209371A1 (en)
EP (1) EP1485437B1 (en)
JP (1) JP4598402B2 (en)
CN (1) CN100379831C (en)
AT (1) ATE328046T1 (en)
AU (1) AU2003217980B2 (en)
BR (1) BR0308167A (en)
CA (1) CA2477296C (en)
DE (1) DE60305666T2 (en)
ES (1) ES2260614T3 (en)
MX (1) MXPA04008641A (en)
WO (1) WO2003076536A1 (en)
ZA (1) ZA200406331B (en)

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Also Published As

Publication number Publication date
DE60305666D1 (en) 2006-07-06
US20050209371A1 (en) 2005-09-22
ATE328046T1 (en) 2006-06-15
CN1756816A (en) 2006-04-05
CN100379831C (en) 2008-04-09
US20090258150A1 (en) 2009-10-15
AU2003217980A1 (en) 2003-09-22
ES2260614T3 (en) 2006-11-01
JP4598402B2 (en) 2010-12-15
ZA200406331B (en) 2007-02-28
CA2477296C (en) 2009-12-22
EP1485437A1 (en) 2004-12-15
AU2003217980B2 (en) 2008-02-14
MXPA04008641A (en) 2005-03-31
EP1485437B1 (en) 2006-05-31
WO2003076536A1 (en) 2003-09-18
US20110020557A1 (en) 2011-01-27
BR0308167A (en) 2005-10-25
JP2005528464A (en) 2005-09-22
US8173726B2 (en) 2012-05-08
DE60305666T2 (en) 2007-05-03

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