CA2476433A1 - Waterborne film-forming compositions containing alternating copolymers of isobutylene type monomers - Google Patents

Waterborne film-forming compositions containing alternating copolymers of isobutylene type monomers Download PDF

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Publication number
CA2476433A1
CA2476433A1 CA 2476433 CA2476433A CA2476433A1 CA 2476433 A1 CA2476433 A1 CA 2476433A1 CA 2476433 CA2476433 CA 2476433 CA 2476433 A CA2476433 A CA 2476433A CA 2476433 A1 CA2476433 A1 CA 2476433A1
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Prior art keywords
group
film
forming composition
monomer
composite coating
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CA 2476433
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French (fr)
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CA2476433C (en
Inventor
Roxalana L. Martin
Edward R. Coleridge
Mark A. Tucker
Mary E. Grolemund
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PPG Industries Ohio Inc
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Ppg Industries Ohio, Inc.
Roxalana L. Martin
Edward R. Coleridge
Mark A. Tucker
Mary E. Grolemund
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Priority claimed from US10/076,984 external-priority patent/US6686432B2/en
Application filed by Ppg Industries Ohio, Inc., Roxalana L. Martin, Edward R. Coleridge, Mark A. Tucker, Mary E. Grolemund filed Critical Ppg Industries Ohio, Inc.
Publication of CA2476433A1 publication Critical patent/CA2476433A1/en
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Publication of CA2476433C publication Critical patent/CA2476433C/en
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds
    • C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31855—Of addition polymer from unsaturated monomers

Abstract

A curable, aqueous film-forming composition is provided that includes a polymeric binder comprising reactive functional groups, a crosslinking agent having at least two functional groups that are reactive with the functional groups of the polymeric binder, and a copolymer flow control agent comprising at least 30 mol % of residues containing alternating residues from a donor monomer and from an acceptor monomer. The copolymer contains at least 15 mol %
of an isobutylene type donor monomer. A multi-component composite coating composition is also provided, comprising a base coat deposited from a pigmented film-forming composition and a transparent topcoat applied over the base coat. The topcoat is deposited from the film-forming composition described above.

Claims (78)

1. A curable, aqueous film-forming composition comprising:
(a) a polymeric binder containing two or more reactive functional groups;
(b) a curing agent having at least two functional groups which are reactive with the reactive functional groups of (a); and (c) a copolymer flow control agent comprising at least 30 mol % of residues having the following alternating structural units:
-[DM-AM]-wherein DM represents a residue from a donor monomer, and AM represents a residue from an acceptor monomer, at least 15 mol % of the copolymer comprising a donor monomer having the following structure (I):
wherein R1 is linear or branched C1 to C4 alkyl, R2 is selected from the group consisting of methyl, linear, cyclic or branched C1 to C20 alkyl, alkenyl, aryl, alkaryl and aralkyl.
2. The film-forming composition of claim 1, wherein at least 15 mol of the copolymer comprises an acrylic monomer as an acceptor monomer.
3. The film-forming composition of claim 1, wherein the copolymer contains at least one salt group or salt forming group.
4. The film-forming composition of claim 1, wherein the copolymer contains hydroxyl functionality.
5. The film-forming composition of claim 1, wherein the copolymer is substantially free of maleate monomer segments and fumarate monomer segments.
6. The film-forming composition of claim 1, wherein the copolymer composition is substantially free of Lewis acids and transition metals.
7. The film-forming composition of claim 1, wherein the donor monomer is one or more selected from the group consisting of isobutylene, diisobutylene, dipentene, and isoprenol optionally in combination with styrene, substituted styrenes, methyl styrene, substituted styrenes, vinyl ethers, and vinyl pyridine.
8. The film-forming composition of claim 1, wherein the donor monomer of structure I is selected from the group consisting of isobutylene, diisobutylene, dipentene, isoprenol, and mixtures thereof.
9. The film-forming composition of claim 1, wherein the group R2 of the donor monomer of structure I includes one or more functional groups selected from the group consisting of hydroxy; epoxy, carboxylic acid, ether, carbamate, and amide.
10. The film-forming composition of claim 1, wherein the acceptor monomer comprises one or more described by the structure (II):
wherein W is selected from the group consisting of -CN, -X, and -C(=O)-Y, wherein Y is selected from the group consisting of -NR3 2,-O-R5-O-C(=O)-NR32, and -OR4, R3 is selected from the group consisting of H, linear or branched C1 to C20 alkyl, and linear or branched C1 to C20 alkylol, R4 is selected from the group consisting.of H, polyethylene oxide); polypropylene oxide), poly(caprolactone), linear or branched C1 to C20 alkyl, alkylol, aryl, alkaryl and aralkyl, linear or branched C1 to C20 fluoroalkyl, fluoroaryl, fluoroalkaryl and fluoroaralkyl, and a polysiloxane radical, R5 is a divalent linear or branched C1 to C20 alkyl linking group, and X is a halide.
11. The film-forming composition of claim 2, wherein the acrylic monomer is one or more described by structure (III) wherein Y is selected from the group consisting of -NR3 2, -O-R5-O-C(=O)-NR3 2, and -OR4, R3 is selected from the group consisting of H, linear or branched C1 to C20 alkyl and linear or branched C1 to C20 alkylol, R4 is selected from the group consisting of H, polyethylene oxide), polypropylene oxide), linear or branched C1 to C20 alkyl, alkylol, aryl, alkaryl and aralkyl, linear or branched C1 to C20 fluoroalkyl, fluoroaryl and fluoroaralkyl, and a polysiloxane radical, and R5 is a divalent linear or branched C1 to C20 alkyl linking group.
12. The film-forming composition of claim 11, wherein Y includes at least one functional group selected from the group consisting of hydroxy, amide, oxazoline, aceto acetate, blocked isocyanate, carbamate, and amine.
13. The film-forming composition of claim 3, in which the salt group is selected from the class consisting of carboxylic acid salt, amine salt, quaternized ammonium, quaternized phosphonium, and ternary sulfonium.
14. The film-forming composition of claim 1, wherein the copolymer has a molecular weight of from 250 to 100,000.
15. The film-forming composition of claim 1, wherein the copolymer has a polydispersity index of less than 4.
16. The film-forming composition of claim 1, wherein the alternating structural units comprise at least 50 mol % of the copolymer.
17. The film-forming composition of claim 1, wherein the acceptor monomer is one or more selected from the group consisting of hydroxyethyl acrylate, hydroxypropyl acrylate, 4-hydroxybutyl acrylate, acrylic acid, methyl.
acrylate, ethyl acrylate, butyl acrylate, isobutyl acrylate, isobornyl acrylate, dimethylaminoethyl acrylate, acrylamide, chlorotrifluoro ethylene, glycidyl acrylate, 2-ethylhexyl acrylate, and n-butoxy methyl acrylamide.
18. The film-forming composition of claim 1, wherein the copolymer comprises one or more residues derived from other ethylenically unsaturated monomers of general formula VII:
wherein R6, R7, and R9 are independently selected from the group consisting of H, CF3, straight or branched alkyl of 1 to 20 carbon atoms, aryl, unsaturated straight or branched alkenyl or alkynyl of 2 to 10 carbon atoms, unsaturated straight or branched alkenyl of 2 to 6 carbon atoms substituted with a halogen, C3-C8 cycloalkyl, heterocyclyl and phenyl, R8 is selected from the group consisting of H, C1-C6 alkyl, and COOR15, wherein R15 is selected from the group consisting of H, an alkali metal, a C1 to C6 alkyl group, glycidyl and aryl.
19. The film-forming composition of claim 18, wherein the other ethylenically unsaturated monomers are one or more selected from the group consisting of methacrylic monomers and allylic monomers.
20. The film-forming composition of claim 1 wherein components (a) and (b) are substantially hydrophobic and are prepared as an aqueous dispersion comprising polymeric microparticles, said microparticles prepared by mixing components (a) and (b) together under high shear conditions, and wherein said film-forming composition is capable of forming a generally continuous film at ambient temperature.
21. The film-forming composition of claim 20, wherein the functional groups of the polymeric binder (a) are selected from the group consisting of hydroxyl, carbamate, blocked isocyanate, primary amine, secondary amine, amide, urea, urethane, vinyl and mixtures thereof.
22. The film-forming composition of claim 20, wherein the polymeric binder (a) contains carbamate functional groups.
23. The film-forming composition of claim 20, wherein the polymeric binder (a) comprises the reaction product of the following reactants:
(1) at least one polymerizable, ethylenically unsaturated monomer containing acid functional group that are subsequently at least partially neutralized with base to form carboxylic acid salt groups; and (2) at least one polymerizable, functional group-containing ethylenically unsaturated monomer free of acid functional groups.
24. The film-forming composition of claim 23, wherein reactant (1) comprises a carboxylic acid group-containing ethylenically unsaturated monomer.
25. The film-forming composition of claim 24, wherein reactant (1) is selected from the group consisting of acrylic acid, methacrylic acid, and mixtures thereof.
26. The film-forming composition of claim 23, wherein, reactant (1) is present in the polymeric binder (a) in an amount sufficient to provide an acid value of up to 50 mg KOH/g.
27. The film-forming composition of claim 23, wherein reactant (2) comprises at least one hydroxyalkyl functional monomer selected from the group, consisting of hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and mixtures thereof.
28. The film-forming composition of claim 23, wherein reactant (2) comprises an ethylenically unsaturated, beta-hydroxy ester functional monomer.
29. The film-forming composition of claim 28, wherein the ethylenically unsaturated, beta-hydroxy ester functional monomer comprises the reaction product of reactants selected from the group consisting of the following:
(1) an ethylenically unsaturated epoxy functional monomer and a saturated carboxylic acid having at least 5 carbon atoms; and (2) an ethylenically unsaturated acid functional monomer and an epoxy compound containing at least 5 carbon atoms which is not polymerizable with the ethylenically unsaturated acid functional monomer.
30. The film-forming composition of claim 23, wherein the reactant from which the polymeric binder (a) informed further comprise reactant (3) at least one polymerizable, ethylenically unsaturated monomer different from (1) and (2).
31: The film-forming composition of claim 30, wherein reactant (3) is selected from the group consisting of vinyl aromatic monomers, alkyl esters of (meth)acrylic acid, and mixtures thereof.
32. The film-forming composition of claim 23, wherein the acid value of the polymeric binder (a) ranges from 0 to 50 mg KOH/g.
33. The film-forming composition of claim 23, wherein the polymeric binder (a) is present in the dispersion in an amount ranging from 55 to 99 weight percent based on total resin solids weight of the dispersion.
34. The film-forming composition of claim 20, wherein the crosslinking agent (b) is selected from the group consisting of blocked isocyanates, aminoplast resins, and mixtures thereof.
35. The film-forming composition of claim 34, wherein the crosslinking agent (b) is an isocyanurate of 1,6-hexamethylene diisocyanate reversibly blocked with 3,5-dimethyl pyrazole.
36. The film-forming composition of claim 20, wherein the crosslinking agent (b) is present in the dispersion in an amount ranging from to 45 weight percent based on total weight of resin solids present in the dispersion.
37. The film-forming composition of claim 20, further comprising at least one hydrophilic crosslinking agent.
38. The film-forming composition of claim 37, wherein the hydrophilic crosslinking agent is selected from the group consisting of hydrophilically modified blocked polyisocyanates, aminoplast resins, tricarbamoyl triazine compounds, and mixtures thereof.
39. The film-forming composition of claim 37, wherein the hydrophilic crosslinking agent is present in the film-forming composition in an amount up to 70 weight percent based on total weight of resin solids present in the composition.
40. A multi-component composite coating composition comprising a base coat deposited from a pigmented film-forming composition and a transparent topcoat composition applied over the base coat in which the transparent topcoat is deposited from a film-forming composition which is substantially free of organic solvent, said topcoat film-forming composition comprising a curable, aqueous film-forming composition comprising:
(a) a polymeric binder containing two or more reactive functional groups;
(b) a curing agent having at least two functional groups which are reactive with the reactive functional groups of (a);and (c) a copolymer flow control agent comprising at least 30 mol % of residues having the following alternating structural units:
-[DM-AM]-wherein DM represents a residue from a donor monomer, AM represents a residue from an acceptor monomer, at least 15 mol % of the copolymer comprising a donor monomer having the following structure (I):
wherein R1 is linear or branched C1 to C4 alkyl, R2 is selected from the group consisting of methyl, linear, cyclic or branched C1 to C20 alkyl, alkenyl, aryl, alkaryl and aralkyl.
41. The multi-component composite coating composition of claim 40, wherein at least 15 mol % of the copolymer comprises an acrylic monomer as an acceptor monomer.
42. The multi-component composite coating composition of claim 40, wherein the copolymer contains at least one salt group or salt forming group.
43. The multi-component composite coating composition of claim 40, wherein the copolymer contains hydroxyl functionality.
44. The multi-component composite coating composition of claim 40, wherein the copolymer is substantially free of maleate monomer segments and fumarate monomer segments.
45. The multi-component composite coating composition of claim 40, wherein the copolymer composition is substantially free of Lewis acids and transition metals.
46. The multi-component composite coating composition of claim 40, wherein the donor monomer is one or more selected from the group consisting of isobutylene, diisobutylene, dipentene, and isoprenol optionally in combination with styrene, substituted styrenes, methyl styrene, substituted styrenes, vinyl ethers, and vinyl pyridine.
47. The multi-component composite coating composition of claim 40, wherein the donor monomer of structure I is selected from the group consisting of isobutylene, diisobutylene, dipentene, isoprenol, and mixtures thereof.
48. The multi-component composite coating composition of claim 40, wherein the group R2 of the donor monomer of structure 1 includes one or more functional groups selected from the group consisting of hydroxy, epoxy;
carboxylic acid, ether, carbamate, and amide.
49. The multi-component composite coating composition of claim 40, wherein the acceptor monomer comprises one or more described by the structure (II):
wherein W is selected from the group consisting. of -CN, -X, and -C(=O)-Y, wherein Y is selected from the group consisting of -NR3 2,-O-R5-O-C(=O)-NR3 2, and -OR4, R3 is selected from the group consisting of H, linear or branched C1 to C20 alkyl, and linear or branched C1 to C20 alkylol, R4 is selected from the group consisting of H, poly(ethylene oxide), poly(propylene oxide), poly(caprolactone), linear or branched C1 to C20 alkyl, alkylol, aryl, alkaryl and aralkyl, linear or branched C1 to C20 fluoroalkyl, fluoroaryl, fluoroalkaryl and fluoroaralkyl, and a polysiloxane radical, R5 is a divalent linear or branched C1 to C20 alkyl linking group, and X is a halide.
50. The multi-component composite coating composition of claim 41, wherein the acrylic monomer is one or more described by structure (III):
wherein Y is selected from the group consisting of -NR3 2, -O-R5-O-C(=O)-NR3 2, and -OR4, R3 is selected from the group consisting of H, linear or branched C1 to C20 alkyl and linear or branched C1 to C20 alkylol, R4 is selected from the group consisting of H, poly(ethylene oxide), poly(propylene oxide), linear or branched C1 to C20 alkyl, alkylol, aryl alkaryl and aralkyl, linear or branched C1 to C20 fluoroalkyl, fluoroaryl and fluoroaralkyl, and a polysiloxane radical, and R5 is a divalent linear or branched C1 to C20 alkyl linking group.
51. The multi-component composite coating composition of claim 50, wherein Y includes at least one functional group selected from the group consisting of hydroxy, amide, oxazoline, aceto acetate, blocked isocyanate, carbamate, and amine.
52. The multi-component composite coating composition of claim 42, in which the salt group is selected from the class consisting of carboxylic acid salt, amine salt, quaternized ammonium, quaternized phosphonium, and ternary sulfonium.
53. The multi-component composite coating composition of claim 40, wherein the copolymer has a molecular weight of from 250 to 100,000.
54. The multi-component composite coating composition of claim 40, wherein the copolymer has a polydispersity index of less than 4.
55: The multi-component composite coating composition of claim 40, wherein the alternating structural units comprise at least 50 mol % of the copolymer.
56. The multi-component composite coating composition of claim 40, wherein the acceptor monomer is one or more selected from the group consisting of hydroxyethyl acrylate, hydroxypropyl acrylate, 4-hydroxybutyl acrylate, acrylic acid, methyl acrylate, ethyl acrylate, butyl acrylate, isobutyl acrylate, isobornyl acrylate, dimethylaminoethyl acrylate, acrylamide, chlorotrifluoro ethylene, glycidyl acrylate, 2-ethylhexyl acrylate, and n-butoxy methyl acrylamide.
57. The multi-component composite coating composition of claim 40, wherein the copolymer comprises one or more residues derived from other ethylenically unsaturated monomers of general formula VII:
wherein R6, R7, and R9 are independently selected from the group consisting of H, CF3, straight or branched alkyl of 1 to 20 carbon atoms, aryl, unsaturated straight or branched alkenyl or alkynyl of 2 to 10 carbon atoms, unsaturated straight or branched alkenyl of 2 to 6 carbon atoms substituted with a halogen, C3-C8 cycloalkyl, heterocyclyl and phenyl, R8 is selected from the group consisting of H, C1-C6 alkyl, and COOR15, wherein R15 is selected from the group consisting of H, an alkali metal, a C1 to C6 alkyl group, glycidyl and aryl:
58. The multi-component composite coating composition of claim 57, wherein the other ethylenically unsaturated monomers are one or more selected from the group consisting of methacrylic monomers and allylic monomers:
59. The multi-component composite coating composition of claim 40, wherein components (a) and (b) are substantially hydrophobic and are prepared as an aqueous dispersion comprising polymeric microparticles, said microparticles prepared by mixing components (a) and (b) together under high shear conditions, and wherein said film-forming composition is capable of forming a generally continuous film at ambient temperature.
60. The multi-component composite coating composition of claim 59, wherein the functional groups of the polymeric binder, (a) are selected from the group consisting of hydroxyl, carbamate, blocked isocyanate, primary amine, secondary amine; amide, urea, urethane, vinyl, and mixtures thereof.
61. The multi-component composite coating composition of claim 59, wherein the polymeric binder (a) contains carbamate functional groups.
62. The multi-component composite coating composition of claim 59, wherein the polymeric binder (a) comprises the reaction product of the following reactants:
(1) at least one polymerizable, ethylenically unsaturated monomer containing acid functional groups that are subsequently at least partially neutralized with base to form carboxylic acid salt groups; and (2) at least one polymerizable, functional group-containing ethylenically unsaturated monomer free of acid functional groups.
63. The multi-component composite coating composition of claim 62, wherein reactant (1) comprises a carboxylic acid group-containing ethylenically unsaturated monomer.
64. The multi-component composite coating composition of claim 63, wherein reactant (1) is selected from the group consisting of acrylic acid, methacrylic acid, and mixtures thereof.
65. The multi-component composite coating composition of claim 62, wherein reactant (1) is present in the polymeric binder (a) in an amount sufficient to provide an acid value of up to 50 mg KOH/g.
66. The multi-component composite coating composition of claim 62, wherein reactant (2) comprises at least one hydroxyalkyl functional monomer selected from the group consisting of hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and mixtures thereof.
67. The multi-component composite coating composition of claim 62, wherein reactant (2) comprises an ethylenically unsaturated, beta-hydroxy ester functional monomer.
68. The multi-component composite coating composition of claim 67, wherein the ethylenically unsaturated, beta-hydroxy ester functional monomer comprises the reaction product of reactants selected from the group consisting of the following:
(1) an ethylenically unsaturated epoxy functional monomer and a saturated carboxylic acid having at least 5 carbon atoms; and (2) an ethylenically unsaturated acid functional monomer and an epoxy compound containing at least 5 carbon atoms which is not polymerizable with the ethylenically unsaturated acid functional monomer.
69. The multi-component composite coating composition of claim 59, wherein the reactants, from which the polymeric binder (a) is formed further comprise reactant (3) at least one polymerizable, ethylenically unsaturated monomer different from (1) and (2).
70. The multi-component composite coating composition of claim 69, wherein reactant (3) is selected from the group consisting of vinyl aromatic monomers, alkyl esters of (meth)acrylic acid, and mixtures thereof.
71. The multi-component composite coating composition of claim 59, wherein the acid value of the polymeric binder (a) ranges from 0 to 50 mg KOH/g.
72. The multi-component composite coating composition of claim 59, wherein the polymeric binder (a) is present in the dispersion in an amount ranging from 55 to 99 weight percent based on total resin solids weight of the dispersion.
73. The multi-component composite coating composition of claim 59, wherein the crosslinking agent (b) is selected from the group consisting of blocked isocyanates, aminoplast resins, and mixtures thereof.
74. The multi-component composite coating composition of claim 73, wherein the crosslinking agent (b) is an isocyanurate of 1,6-hexamethylene diisocyanate reversibly blocked with 3,5-dimethyl pyrazole.
75. The multi-component composite coating composition of claim 59, wherein the crosslinking agent (b) is present in the dispersion in an amount ranging from 1 to 45 weight percent based on total weight of resin solids present in the dispersion.
76. The multi-component composite coating composition of claim 59, wherein the topcoat film-forming composition further comprises at least one hydrophilic crosslinking agent.
77. The multi-component composite coating composition of claim 76, wherein the hydrophilic crosslinking agent is selected from the group consisting of hydrophilically modified blocked polyisocyanates, aminoplast resins, tricarbamoyl triazine compounds, and mixtures thereof.
78. The multi-component composite coating composition of claim 76, wherein the hydrophilic crosslinking agent is present in the topcoat film-forming composition in an amount up to 70 weight percent based on the total weight of resin solids present in the topcoat film-forming composition.
CA 2476433 2002-02-15 2003-02-12 Waterborne film-forming compositions containing alternating copolymers of isobutylene type monomers Expired - Fee Related CA2476433C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US10/076,984 US6686432B2 (en) 2002-02-15 2002-02-15 Alternating copolymers of isobutylene type monomers
US10/076,984 2002-02-15
US10/357,797 2003-02-04
US10/357,797 US6787597B1 (en) 2002-02-15 2003-02-04 Waterborne film-forming compositions containing alternating copolymers of isobutylene type monomers
PCT/US2003/004098 WO2003070783A1 (en) 2002-02-15 2003-02-12 Waterborne film-forming compositions containing alternating copolymers of isobutylene type monomers

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CA2476433A1 true CA2476433A1 (en) 2003-08-28
CA2476433C CA2476433C (en) 2010-06-22

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US (1) US7101930B2 (en)
EP (1) EP1474453B1 (en)
JP (2) JP2005517776A (en)
CN (1) CN1308358C (en)
AU (1) AU2003219738B2 (en)
BR (1) BR0307662A (en)
CA (1) CA2476433C (en)
DE (1) DE60315133T2 (en)
ES (1) ES2290444T3 (en)
WO (1) WO2003070783A1 (en)

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AU2003219738A1 (en) 2003-09-09
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US7101930B2 (en) 2006-09-05
WO2003070783A1 (en) 2003-08-28
AU2003219738B2 (en) 2005-07-14
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CA2476433C (en) 2010-06-22
US20040249077A1 (en) 2004-12-09

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