CA2670055A1 - Waterborne, radiation-curable coating compositions and related methods - Google Patents

Waterborne, radiation-curable coating compositions and related methods Download PDF

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Publication number
CA2670055A1
CA2670055A1 CA002670055A CA2670055A CA2670055A1 CA 2670055 A1 CA2670055 A1 CA 2670055A1 CA 002670055 A CA002670055 A CA 002670055A CA 2670055 A CA2670055 A CA 2670055A CA 2670055 A1 CA2670055 A1 CA 2670055A1
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CA
Canada
Prior art keywords
coating composition
neutralizing agent
ethylenically unsaturated
composition
unsaturated compound
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
CA002670055A
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French (fr)
Other versions
CA2670055C (en
Inventor
M. Lisa Perrine
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.)
PPG Industries Ohio Inc
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Individual
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 Individual filed Critical Individual
Publication of CA2670055A1 publication Critical patent/CA2670055A1/en
Application granted granted Critical
Publication of CA2670055C publication Critical patent/CA2670055C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/44—Preparation of metal salts or ammonium salts
    • 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
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/101—Esters; Ether-esters of monocarboxylic acids
    • C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
    • 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
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0025—Crosslinking or vulcanising agents; including accelerators

Abstract

Disclosed are waterborne, radiation-curable coating compositions. These coating compositions include a water-dispersible polymer and a hydrophobic multi-functional ethylenically unsaturated compound. The compositions are characterized by being viscosity stable at elevated temperatures and alkaline conditions.

Claims (20)

1. A waterborne, radiation-curable coating composition comprising:
(a) a water dispersible polymer;
(b) a hydrophobic multi-functional ethylenically unsaturated compound; and (c) a neutralizing agent comprising predominantly a monofunctional tertiary amine having a pK a of no more than 9.5.
2. The coating composition of claim 1, wherein the composition comprises a carrier fluid that is at least 80 weight percent water.
3. The coating composition of claim 1, wherein the water dispersible polymer comprises an acid functional polymer.
4. The coating composition of claim 3, wherein the acid functional polymer comprises a carboxylic acid functional vinyl polymer.
5. The coating composition of claim 1, wherein the water dispersible polymer is present in the coating composition in an amount of from 5 percent to 50 percent by weight, based on the total weight of the coating composition.
6. The coating composition of claim 1, wherein the hydrophobic multi-functional ethylenically unsaturated compound comprises three or more sites of ethylenic unsaturation per molecule.
7. The coating composition of claim 5, wherein the hydrophobic multi-functional ethylenically unsaturated compound comprises trimethylolpropane tri(meth)acrylate.
8. The coating composition of claim 1, wherein the hydrophobic multi-functional ethylenically unsaturated compound is present in the coating composition in an amount of from 2 percent to 30 percent by weight, based on the total weight of the coating composition.
9. The coating composition of claim 1, wherein the neutralizing agent comprises predominantly a monofunctional tertiary amine having a pKa of no more than 8Ø
10. The coating composition of claim 1, wherein the neutralizing agent comprises n-ethylmorpholine.
11. The coating composition of claim 1, wherein the neutralizing agent is present in an amount sufficient to neutralize the coating composition to a pH within the range of 7.5 to 8.7.
12. The coating composition of claim 1, wherein the initial viscosity of the composition is 100 to 300 centipoise at 77°F and the final viscosity is 100 to 450 cps at 77°F.
13. A waterborne, radiation curable coating composition comprising:
(a) a water dispersible polymer, and (b) a hydrophobic multi-functional ethylenically unsaturated compound, wherein the composition is viscosity stable for at least 28 days at 120°F when neutralized to a pH of from 7 to 9.
14. The coating composition of claim 13, wherein the water dispersible polymer comprises an acid functional polymer.
15. The coating composition of claim 14, wherein the acid functional polymer comprises a carboxylic acid functional vinyl polymer.
16. The coating composition of claim 13, wherein the hydrophobic multi-functional ethylenically unsaturated compound comprises three or more sites of ethylenic unsaturation per molecule.
17. The coating composition of claim 13, comprising a neutralizing agent comprising predominantly a monofunctional tertiary amine having a pK a of no more than 8Ø
18. The coating composition of claim 17, wherein the neutralizing agent comprises n-ethylmorpholine.
19. The coating composition of claim 17, wherein the neutralizing agent is present in an amount sufficient to neutralize the coating composition to a pH within the range of 7.5 to 8.7.
20. The coating composition of claim 13, wherein the initial viscosity of the composition is 100 to 300 centipoise at 77°F and the final viscosity is 100 to 450 cps at 77°F.
CA2670055A 2006-11-21 2007-11-07 Waterborne, radiation-curable coating compositions and related methods Expired - Fee Related CA2670055C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US11/562,069 2006-11-21
US11/562,069 US8138262B2 (en) 2006-11-21 2006-11-21 Waterborne, radiation-curable coating compositions and related methods
PCT/US2007/083892 WO2008063887A2 (en) 2006-11-21 2007-11-07 Waterborne, radiation-curable coating compositions and related methods

Publications (2)

Publication Number Publication Date
CA2670055A1 true CA2670055A1 (en) 2008-05-29
CA2670055C CA2670055C (en) 2012-05-15

Family

ID=39310906

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2670055A Expired - Fee Related CA2670055C (en) 2006-11-21 2007-11-07 Waterborne, radiation-curable coating compositions and related methods

Country Status (16)

Country Link
US (2) US8138262B2 (en)
EP (2) EP2091976B1 (en)
KR (1) KR101116435B1 (en)
CN (1) CN101563370B (en)
AR (1) AR064255A1 (en)
AU (1) AU2007323973B2 (en)
BR (1) BRPI0717662A2 (en)
CA (1) CA2670055C (en)
CL (1) CL2007003339A1 (en)
HK (1) HK1135419A1 (en)
MY (1) MY145781A (en)
NO (1) NO20092204L (en)
NZ (1) NZ577082A (en)
PL (2) PL2527372T3 (en)
TW (1) TWI424032B (en)
WO (1) WO2008063887A2 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004090020A1 (en) 2003-04-02 2004-10-21 Valspar Sourcing, Inc. Aqueous dispersions and coatings
ATE513025T1 (en) 2004-10-20 2011-07-15 Valspar Sourcing Inc COATING COMPOSITIONS FOR CANS AND COATING PROCESSES
JP5247660B2 (en) * 2009-11-12 2013-07-24 キヤノン株式会社 Toner image fixing method
EP2749606B1 (en) 2012-12-21 2018-11-21 Rohm and Haas Company Acrylic dispersions with multi-functional acrylates for UV-cure coatings
US11795937B2 (en) 2020-01-08 2023-10-24 Baker Hughes Oilfield Operations, Llc Torque monitoring of electrical submersible pump assembly

Family Cites Families (18)

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US4186036A (en) 1978-08-25 1980-01-29 The Dow Chemical Company Weldable coating compositions
US4157924A (en) 1978-08-25 1979-06-12 The Dow Chemical Company Process of applying weldable coating compositions to a metallic substrate
JPH02230152A (en) 1987-06-18 1990-09-12 Napp Syst Usa Inc Photosensitive resin composition
AU621845B2 (en) * 1987-12-17 1992-03-26 B.F. Goodrich Company, The An improved process for preparing elastomeric coatings on fibers and compositions of water-dispersed polymers
US5045435A (en) 1988-11-25 1991-09-03 Armstrong World Industries, Inc. Water-borne, alkali-developable, photoresist coating compositions and their preparation
JPH07170054A (en) 1993-12-14 1995-07-04 Canon Inc Ultraviolet hardening composition, formation of pattern using this and manufacture of wiring board
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JP2002121207A (en) * 2000-10-16 2002-04-23 Kanegafuchi Chem Ind Co Ltd Composition, photosensitive composition using the same, and cover lay
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Also Published As

Publication number Publication date
CN101563370B (en) 2013-03-20
TWI424032B (en) 2014-01-21
BRPI0717662A2 (en) 2014-02-25
EP2091976B1 (en) 2021-05-05
TW200837158A (en) 2008-09-16
US8138262B2 (en) 2012-03-20
AU2007323973B2 (en) 2010-06-10
US20080139708A1 (en) 2008-06-12
KR20090086601A (en) 2009-08-13
US20120142818A1 (en) 2012-06-07
CA2670055C (en) 2012-05-15
CL2007003339A1 (en) 2008-07-04
MY145781A (en) 2012-04-30
PL2527372T3 (en) 2021-10-04
CN101563370A (en) 2009-10-21
NO20092204L (en) 2009-08-14
EP2527372B1 (en) 2021-05-26
KR101116435B1 (en) 2012-03-07
HK1135419A1 (en) 2010-06-04
WO2008063887A3 (en) 2008-08-14
NZ577082A (en) 2012-01-12
AU2007323973A1 (en) 2008-05-29
EP2527372A1 (en) 2012-11-28
PL2091976T3 (en) 2021-08-16
WO2008063887A2 (en) 2008-05-29
EP2091976A2 (en) 2009-08-26
AR064255A1 (en) 2009-03-25

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