CA2476090A1 - Thermosetting compositions containing alternating copolymers of isobutylene type monomers - Google Patents

Thermosetting compositions containing alternating copolymers of isobutylene type monomers Download PDF

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Publication number
CA2476090A1
CA2476090A1 CA 2476090 CA2476090A CA2476090A1 CA 2476090 A1 CA2476090 A1 CA 2476090A1 CA 2476090 CA2476090 CA 2476090 CA 2476090 A CA2476090 A CA 2476090A CA 2476090 A1 CA2476090 A1 CA 2476090A1
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Prior art keywords
group
composition
acrylate
copolymer
functional groups
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CA 2476090
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French (fr)
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CA2476090C (en
Inventor
Simion Coca
Edward R. Coleridge
Gregory J. Mccollum
James B. O'dwyer
James E. Poole
Victoria A. Trettel
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PPG Industries Ohio Inc
Original Assignee
Ppg Industries Ohio, Inc.
Simion Coca
Edward R. Coleridge
Gregory J. Mccollum
James B. O'dwyer
James E. Poole
Victoria A. Trettel
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Application filed by Ppg Industries Ohio, Inc., Simion Coca, Edward R. Coleridge, Gregory J. Mccollum, James B. O'dwyer, James E. Poole, Victoria A. Trettel filed Critical Ppg Industries Ohio, Inc.
Publication of CA2476090A1 publication Critical patent/CA2476090A1/en
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Publication of CA2476090C publication Critical patent/CA2476090C/en
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/50—Multilayers
    • B05D7/56—Three layers or more
    • B05D7/57—Three layers or more the last layer being a clear coat
    • C—CHEMISTRY; METALLURGY
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/02—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
    • B05D3/0209—Multistage baking
    • 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
    • C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F210/04—Monomers containing three or four carbon atoms
    • C08F210/08—Butenes
    • C08F210/10—Isobutene
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    • 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
    • C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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    • C—CHEMISTRY; METALLURGY
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/04—Polymers provided for in subclasses C08C or C08F
    • C08F290/046—Polymers of unsaturated carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C—CHEMISTRY; METALLURGY
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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    • 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
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    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
    • C08G18/6225—Polymers of esters of acrylic or methacrylic acid
    • C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
    • 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
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    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
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    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/798—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing urethdione groups
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    • 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
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
    • C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
    • C08G18/8022—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203 with polyols having at least three hydroxy groups
    • C08G18/8025—Masked aliphatic or cycloaliphatic polyisocyanates
    • 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
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
    • 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
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
    • C08G18/8074—Lactams
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
    • C08L23/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
    • C08L23/22—Copolymers of isobutene; Butyl rubber ; Homo- or copolymers of other iso-olefins
    • 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
    • C09D123/00—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers
    • C09D123/02—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
    • C09D123/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
    • C09D123/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
    • C09D123/22—Copolymers of isobutene; Butyl rubber ; Homo- or copolymers of other iso-olefines
    • 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
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    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D1/00—Processes for applying liquids or other fluent materials
    • B05D1/007—Processes for applying liquids or other fluent materials using an electrostatic field
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
    • B05D3/061—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation using U.V.
    • B05D3/065—After-treatment
    • B05D3/067—Curing or cross-linking the coating
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
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    • 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
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    • 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
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    • 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
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Abstract

A thermosetting composition that includes an ungelled copolymer composition and a crosslinking agent. The ungelled copolymer composition includes a functional group-containing copolymer that includes segments of alternating residues derived from a donor monomer composition comprising an acceptor monomer composition. The donor monomer composition includes one or both of isobutylene and diisobutylene, and the acceptor monomer composition includes acrylic monomers and monomers containing functional groups. The ungelled copolymer composition is substantially free of transition metals and Lewis acids, and the copolymer is substantially free of maleate-type monomer residues and fumarate-type monomer residues. The crosslinking agent has at least two functional groups that are reactive with the functional groups of the copolymer. The thermosetting composition may be in liquid, powder, or dispersed form and may be applied by traditional or electrocoating methods.

Claims (143)

1. A liquid thermosetting composition comprising:
(a) an ungelled copolymer composition comprising segments comprising alternating residues derived from a donor monomer composition comprising one or more monomers selected from the group consisting of isobutylene; diisobutylene, dipentene, and isoprenol and an acceptor monomer composition comprising acrylic monomers and monomers containing functional groups, wherein said ungelled copolymer composition is substantially free of transition metals, lewis acids, maleate-type monomer residues, and fumarate-type monomer residues; and (b) a crosslinking agent having at least two functional groups that are reactive with the functional groups of the copolymer (a).
2. The thermosetting composition of claim 1, wherein the copolymer has a number average molecular weight of from 500 to 16,000 and a polydispersity index of less than 4.
3. The thermosetting composition of claim 1, wherein the acceptor monomer composition further comprises acrylonitrile.
4. The thermosetting composition of claim 1, wherein the acrylic monomers are one or more described by. structure (III):
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, poly(ethylene oxide), poly(propylene oxide), linear or branched C1 to C20 alkyl, alkylol, aryl and aralkyl, linear or branched C1 to C20 fluoroalkyl, fluoroaryl and fluoroaralkyl, a siloxane, a polysiloxane, an alkyl siloxane, an ethoxylated trimethylsilyl siloxane, and a propoxylated trimethylsilyl siloxane, and R5 is a divalent linear or branched C1 to C20 alkyl linking group.
5. The thermosetting composition of claim 1, wherein the monomers containing functional groups have structure (IV):
wherein R10 is H or C1-C4 alkyl and Y represents at least one group selected from the group consisting of C1 to C20 alkyl, aryl, alkaryl and aralkyl containing one or more functional groups selected from the group consisting of epoxy, oxirane, carboxylic acid, hydroxy, amide, oxazoline, aceto acetate, isocyanate, carbamate, amine, amine salt, quaternized amine, thioether, sulfide, sulfonium salt, and phosphate.
6. The thermosetting composition of claim 4, wherein the acceptor monomer composition comprises one or more selected from the group consisting of methyl acrylate, ethyl acrylate, butyl acrylate, isobutyl acrylate, isobornyl acrylate, 2-ethyl hexyl acrylate, and chlorotrifluoro ethylene.
7. The thermosetting composition of claim 5, wherein the acrylic monomers containing functional groups are one or more selected from the group consisting of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, acrylic acid, methacrylic acid, acrylamide, methacrylamide, glycidyl acrylate, glycidyl methacrylate, 2-isocyanatoethyl acrylate, 2-isocyanatoethyl methacrylate, 2-isocyanatopropyl acrylate, 2-isocyanatopropyl methacrylate, 2-oxazoline ethyl acrylate, 2-oxazoline ethyl methacrylate, 2-oxazoline propyl acrylate, 2-oxazoline propyl (meth)acrylate, aceto acetate ester of hydroxyethyl acrylate, aceto acetate ester of hydroxyethyl methacrylate, aceto acetate ester of hydroxypropyl acrylate, aceto acetate ester of hydroxypropyl methacrylate, 2-carbamoyloxyethyl (meth)acrylate, 2-carbamoyloxyethyl acrylate, 2-carbamyloyloxypropryl methacrylate, n-butoxy methyl acrylamide, and n-butoxy methyl methacrylamide.
8. The thermosetting composition of claim 1, wherein the copolymer further comprises one or more monomer residues derived from monomers of the general formula V:
wherein R11, R12, and R14 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, R13 is selected from the group consisting of H, C1-C6 alkyl, COOR15, wherein R15 is selected from the group consisting of H, an alkali metal, a C1 to C6 alkyl group, and aryl.
9. The thermosetting composition of claim 1, wherein the monomers containing functional groups in the copolymer (a) have functional groups selected from the group consisting of epoxy, oxirane, carboxylic acid, hydroxy, amide, oxazoline, aceto acetate, isocyanate, methylol, methylol ether and carbamate, wherein the functional groups of the crosslinking agent (b) are reactive with tho se in the copolymer (a), and wherein the functional groups of the crosslinking agent (b) are selected from the group consisting of epoxy, oxirane, carboxylic acid, hydroxy, polyol, isocyanate, capped isocyanate, amine, aminoplast, methylol, methylol ether, and beta-hydroxyalkylamide.
10. The thermosetting composition of claim 9, wherein the functional group of the monomers containing functional groups is hydroxy and the functional group of the crosslinking agent (b) is a capped polyisocyanate, wherein the capping group of the capped polyisocyanate crosslinking agent is selected from the group consisting of hydroxy functional compounds, 1H-azoles, lactams, ketoximes, and mixtures thereof.
11. The thermosetting composition of claim 10, wherein the capping group is selected from the group consisting of phenol, p-hydroxy methylbenzoate, 1H-1,2,4-triazole, 1H-2,5-dimethyl pyrazole, 2-propanone oxime, 2-butanone oxime, cyclohexanone oxime, e-caprolactam, and mixtures thereof.
12. The thermosetting composition of claim 10, wherein the polyisocyanate of said capped polyisocyanate crosslinking agent is selected from the group consisting of 1,6-hexamethylene diisocyanate, cyclohexane diisocyanate, .alpha.,.alpha.'-xylylene diisocyanate, .alpha.,.alpha.,.alpha.' ,.alpha.'-tetramethylxylylene diisocyanate, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane, diisocyanato-dicyclohexylmethane, dimers of said polyisocyanates, trimers of said polyisocyanates, and mixtures thereof.
13. The thermosetting composition of claim 1, wherein the functional polymer has a functional group equivalent weight of from 100 to 5,000 grams / equivalent.
14. The thermosetting composition of claim 10, wherein the equivalent ratio of isocyanate equivalents in the capped polyisocyanate.crosslinking agent to hydroxy equivalents in the hydroxy functional copolymer is within the range of 1:3 to 3:1.
15. The thermosetting composition of claim 10, wherein the capped polyisocyanate crosslinking agent is present in an amount of from 1 to 45 percent by weight, based on total weight of resin solids, and the hydroxy functional copolymer is present in an amount of from 55 to 99 percent by weight, based on total weight of resin solids.
16. The thermosetting composition of claim 9, wherein the monomers containing functional groups contain oxirane functional groups and the crosslinking agent (b) is a carboxylic acid, functional compound having from 4 to 20 carbon atoms.
17. The thermosetting composition of claim 16, wherein the carboxylic acid crosslinking agent is.selected from the group consisting of dodecanedioic acid, azelaic acid, adipic acid, 1,6-hexanedioic acid, succinic acid, pimelic acid, sebacic acid, maleic acid, citric acid, itaconic acid, aconitic acid, and mixtures thereof.
18. The thermosetting composition of claim 9, wherein the monomers containing functional groups contain carboxylic acid functional groups and the crosslinking agent (b) is a beta-hydroxyalkylamide compound.
19. The thermosetting.composition of claim 18, further comprising a second polycarboxylic acid functional material selected from the group consisting of C4 to C20 aliphatic carboxylic acids, polymeric polyanhydrides, polyesters, polyurethanes, and mixtures thereof.
20. The thermosetting composition of claim 18, wherein the beta-hydroxyalkylamide is represented by the following formula:

wherein R24 is H or C1-C5 alkyl; R25 is H, C1-C5 alkyl or for which R24 is as described above, E is a chemical bond or monovalent or polyvalent organic radical derived from saturated, unsaturated, or aromatic hydrocarbon radicals including substituted hydrocarbon radicals containing from 2 to 20 carbon atoms, m is 1 or 2, n is from 0 to 2, and m+n is at least 2.
21. A thermosetting composition comprising a resinous phase dispersed in an aqueous medium, said resinous phase comprising the following components:
(a) an ungelled copolymer composition comprising segments comprised of alternating residues derived from a donor monomer composition comprising one or more monomers selected from the group consisting of isobutylene, diisobutylene, dipentene and isoprenol, residues from an acceptor monomer composition comprising acrylic monomers, and residues from monomers containing functional groups which include functional monomers with a functional group containing one or more active hydrogen groups and residues from monomers containing ionic groups, wherein said ungelled copolymer composition is substantially free of transition metals, Lewis acids, maleate-type monomer residues, and fumarate-type monomer residues; and (b) a curing agent having at least two functional groups which are reactive with the active hydrogen-containing functional groups of (a).
22. The thermosetting composition of claim 21, wherein the active hydrogen group-containing copolymer has a number average molecular weight in the range of from 1,000 to 30,000.
23. The thermosetting composition of claim 21, wherein the acceptor monomer composition further comprises up to 25 mol % of acrylonitrile.
24. The thermosetting composition of claim 21, wherein the acrylic monomers are 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), glycidyl, linear or branched C1 to C20 alkyl, alkylol, aryl and aralkyl, linear or branched C1 to C20 fluoroalkyl, fluoroaryl and fluoroaralkyl, a siloxane, a polysiloxane, an alkyl siloxane, an ethoxylated trimethylsilyl siloxane and a propoxylated trimethylsilyl siloxane, and R5 is a divalent linear or branched C1 to C20 alkyl linking group.
25. The thermosetting composition of claim 21, wherein the monomers containing active hydrogen groups have structure (IV):

wherein R10 is H or C1-C4 alkyl and Y represents at least one group selected from the group consisting of C1 to C20 alkyl, aryl, alkaryl, and aralkyl containing one or more functional groups selected from the group consisting of carboxylic acid, hydroxy, amide, alkylol, primary amine, secondary amine, amine salt, quaternized amine, thioether, sulfide, sulfonium salt, phosphate, and carbamate.
26. The thermosetting composition of claim 21, wherein the acceptor monomer composition comprises one or more selected from the group consisting of methyl acrylate, ethyl acrylate, butyl acrylate, isobutyl acrylate, isobornyl acrylate, glycidyl acrylate, 2-ethyl hexyl acrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, acrylic acid, dimethylaminoethyl acrylate, acrylamide, chlorotrifluoro ethylene, and n-butoxy methyl acrylamide.
27. The thermosetting composition of claim 25, wherein the acrylic monomers containing active hydrogen groups are one or more selected from the group consisting of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, hydroxypropyl methacrylate, acrylic acid, methacrylic acid, acrylamide, methacrylamide, 2-carbamoyloxyethyl acrylate, 2-carbamoyloxyethyl methacrylate, 2-carbamyloyloxypropryl acrylate, and 2-carbamyloyloxypropryl methacrylate.
28. The thermosetting composition of claim 21, wherein the copolymer further comprises one or more monomer residues derived from monomers of the general formula V:

wherein R11, R12, and R14 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, R13 is selected from the group consisting of H, C1-C6 alkyl, COOR15, wherein R15 is selected from the group consisting of H, an alkali metal, a C1 to C6 alkyl group, glycidyl, and aryl.
29. The thermosetting composition of claim 2l, wherein the monomers containing active hydrogen groups in the copolymer (a) have functional groups selected from the group consisting of carboxylic acid, hydroxy, amide, amine, aceto acetate, methylol, methylol ether and carbamate, wherein the functional groups of the curing agent (b) are reactive with those in the copolymer (a), and wherein the functional groups of the curing agent (b) are selected from the group consisting of epoxy, carboxylic acid, hydroxy, polyol, isocyanate, capped isocyanate, aceto acetate, amine, aminoplast, and beta-hydroxyalkylamide.
30. The thermosetting composition of claim 29, wherein the functional group of the monomers containing active hydrogen groups is hydroxy and the functional group of the curing agent (b) is a capped polyisocyanate, wherein the capping group of the capped polyisocyanate crosslinking agent is selected from the group consisting of hydroxy functional compounds, 1H-azoles, lactams, ketoximes, and mixtures thereof.
31. The thermosetting composition of claim 30, wherein the capping group is selected from the group consisting of phenol, p-hydroxy methylbenzoate, 1H-1,2,4-triazole, 1H-2,5-dimethyl pyrazole, 2-propanone oxime, 2-butanone oxime, cyclohexanone oxime, e-caprolactam, and mixtures thereof.
32. The thermosetting composition of claim 30, wherein the polyisocyanate of said capped polyisocyanate curing agent is selected from the group consisting of 1,6-hexamethylene diisocyanate, cyclohexane diisocyanate, .alpha.,.alpha.'-xylylene diisocyanate, .alpha.,.alpha.,.alpha.',.alpha.'-tetramethylxylylene diisocyanate, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane, diisocyanato-dicyclohexylmethane, dimers of said polyisocyanates, trimers of said polyisocyanates, and mixtures thereof.
33. The thermosetting composition of claim 21, wherein the functional copolymer has a functional group equivalent weight of from 100 to 5,000 grams / equivalent.
34. The thermosetting composition of claim 21, wherein the equivalent ratio of functional group equivalents in the curing agent to functional group equivalents in the functional copolymer is within the range of 1:3 to 3:1.
35. The thermosetting composition of claim 21, wherein the curing agent is present in an amount of from 1 to 45 percent by weight, based on total weight of resin solids, and the functional copolymer is present in an amount of from 55 to 99 percent by weight, based on total weight of resin solids.
36. The thermosetting composition of claim 29, wherein the monomers containing active hydrogen groups contain carboxylic acid functional groups and the curing agent (b) is a beta-hydroxyalkylamide compound.
37. The thermosetting composition of claim 36, further comprising a second polycarboxylic acid functional material selected from the group consisting of C4 to C20 aliphatic carboxylic acids, polymeric polyanhydrides, polyesters, polyurethanes, and mixtures thereof.
38. The thermosetting composition of claim 36, wherein the beta-hydroxyalkylamide is represented by the following formula:

wherein R24 is H or C1-C5 alkyl; R25 is H, C1-C5 alkyl or for which R24 is as described above, E is a chemical bond or monovalent or polyvalent organic radical derived from saturated, unsaturated, or aromatic hydrocarbon radicals including substituted hydrocarbon radicals containing from 2 to 20 carbon atoms, m is 1 or 2, n is from 0 to 2, and m+n is at least 2.
39. The thermosetting composition of claim 21, wherein the ionic group is an onium salt group and the copolymer has an onium salt group equivalent weight of from 1,000 to 15,000 grams/equivalent.
40. The thermosetting composition of claim 21, wherein the ionic group is an onium salt group and the onium salt functional monomers are selected from at least one of the class consisting of amine salts, quaternary ammonium salts and ternary sulfonium salts.
41. The thermosetting composition of claim 21, wherein the ionic group is an onium salt group and the onium salt functional monomers include at least one selected from the group consisting of an epoxy group-containing ethylenically unsaturated monomer which after polymerization has been post-reacted with an amine acid salt and an amine acid salt of dimethyl aminoethyl acrylate or dimethyl aminoethyl methacrylate.
42. The thermosetting composition of claim 40, wherein the onium salt functional monomers are derived from at least one epoxy group-containing monomer which after polymerization has been post-reacted with a sulfide in the presence of an acid.
43. The thermosetting composition of claim 21, wherein the copolymer is a substantially linear polymer having a number average molecular weight in the range of from 1,000 to 30,000, and wherein ionic group is an opium salt group and the opium salt functional monomer is derived from at least one epoxy group-containing monomer which after polymerization has been post-reacted with an amine acid salt;
the monomers containing active hydrogen groups are at least one hydroxy-alkyl (meth)acrylate having 1 to 4 carbon atoms in the alkyl group; and the acceptor monomer composition includes at least one acrylate monomer.
44. The thermosetting composition of claim 21, wherein component (a) is present in an amount ranging from 25 to 99 weight percent, and component (b) is present in an amount ranging from 1 to 75 weight percent, and wherein the weight percentages are based on the total weight of (a) and (b).
45. A thermosetting composition comprising a co-reactable solid, particulate mixture of:
(a) a reactant having at least two functional groups; and (b) a copolymer composition comprising segments comprising alternating residues derived from a donor monomer composition comprising one or more monomers selected from the group consisting of isobutylene, diisobutylene, dipentene, and isoprenol, and an acceptor monomer composition comprising acrylic monomers, and monomers containing functional groups, wherein said copolymer composition is substantially free of transition metals, Lewis acids, maleate-type monomer residues and fumarate-type monomer residues, and wherein the functional groups of (a) are reactive with the functional groups of (b).
46. The thermosetting composition of claim 45, wherein the functional groups of the reactant (a) are selected from the group consisting of epoxy, oxirane, carboxylic acid, hydroxy, polyol, isocyanate, capped isocyanate, amine, aminoplast, aceto acetate, methylol, methylol ether and beta-hydroxyalkylamide, the functional groups of the copolymer (b) are selected from the group consisting of epoxy, oxirane, carboxylic acid, hydroxy, amide, oxazoline, aceto acetate, methylol, methylol ether, isocyanate, and carbamate; and wherein the functional groups of the reactant (a) are reactive with those in the nonrandom copolymer (b).
47. The thermosetting composition of claim 45, wherein the monomers containing functional groups of the copolymer (b) have hydroxy functional groups and the reactant in (a) is a capped polyisocyanate crosslinking agent, wherein the capping group of the capped polyisocyanate crosslinking agent is selected from the group consisting of hydroxy functional compounds, 1H-azoles, lactams, ketoximes, and mixtures thereof.
48. The thermosetting composition of claim 47, wherein the capping group is selected from the group consisting of phenol, p-hydroxy methylbenzoate, 1H-1,2,4-triazole, 1H-2,5-dimethyl pyrazole, 2-propanone oxime, 2-butanone oxime, cyclohexanone oxime, e-caprolactam, and mixtures thereof.
49. The thermosetting composition of claim 47, wherein the polyisocyanate of said capped polyisocyanate crosslinking agent is selected from the group consisting of 1,6-hexamethylene diisocyanate, cyclohexane diisocyanate, .alpha.,.alpha.'-xylylene diisocyanate, .alpha.,.alpha.,.alpha.',.alpha.'-tetramethylxylylene diisocyanate, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane, 2,4,4-trimethyl hexamethylene diisocyanate, 2,2,4-trimethyl hexamethylene diisocyanate, diisocyanato-dicyclohexylmethane, dimers of said polyisocyanates, trimers of said polyisocyanates, and mixtures thereof.
50. The thermosetting composition of claim 45, wherein the copolymer has a number average molecular weight of from 500 to 16,000 and a polydispersity index of less than 4.
51. The thermosetting composition of claim 45, wherein the functional polymer has a functional group equivalent weight of from 100 to 5,000 grams / equivalent.
52. The thermosetting composition of claim 45, wherein the equivalent ratio of functional group equivalents in said crosslinking agent (a) to functional group equivalents in said hydroxy functional copolymer (b) is within the range of 1:3 to 3:1.
53. The thermosetting composition of claim 45, wherein said crosslinking agent is present in an amount of from 1 to 45 percent by weight, based on total weight of resin solids, and said functional polymer is present in an amount of from 55 to 99 percent by weight, based on total weight of resin solids.
54. The thermosetting composition of claim 45, wherein the monomers containing functional groups of the copolymer (b) include monomers having oxirane functionality and the reactant (a) is a carboxylic functional reactant having from 4 to 20 carbon atoms.
55. The thermosetting composition of claim 54, wherein the carboxylic acid reactant is selected from the group consisting of dodecanedioic acid, azelaic acid, adipic acid, 1,6-hexanedioic acid, succinic acid, pimelic acid, sebacic acid, maleic acid, citric acid, itaconic acid, aconitic acid, and mixtures thereof.
56. The thermosetting composition of claim 45, wherein the monomers containing functional groups of the copolymer (b) include monomers having carboxylic functional groups and the reactant (a) is a beta-hydroxyalkylamide.
57. The thermosetting composition of claim 56, further comprising a second polycarboxylic acid functional material selected from the group consisting of C4 to C20 aliphatic carboxylic acids, polymeric polyanhydrides, polyesters, polyurethanes, and mixtures thereof.
58. The thermosetting composition of claim 56, wherein the beta-hydroxyalkylamide is represented by the following formula:

wherein R24 is H or C1-C5 alkyl, R25 is H, C1-C5 alkyl or for which R24 is as described above, E is a chemical bond or monovalent or polyvalent organic radical derived from saturated, unsaturated, or aromatic hydrocarbon radicals including substituted hydrocarbon radicals containing from 2 to 20 carbon atoms, m is 1 or 2, n is from 0 to 2, and m+n is at least 2.
59. The thermosetting composition of claim 45, wherein the acceptor monomer composition further comprises up to 25 mol % of acrylonitrile.
60. The thermosetting composition of claim 45, wherein the acrylic monomers are 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, R31 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 and aralkyl, linear or branched C1 to C20 fluoroalkyl, fluoroaryl and fluoroaralkyl, a siloxane, a polysiloxane, an alkyl siloxane, an ethoxylated trimethylsilyl siloxane and a propoxylated trimethylsilyl siloxane, and R5 is a divalent linear or branched C1 to C20 alkyl linking group.
61. The thermosetting composition of claim 45, wherein the monomers containing functional groups have structure (IV):

wherein R10 is H or C1-C4 alkyl and Y represents at least one group selected from the group consisting of C1 to C20 alkyl, aryl, and aralkyl containing one or more functional groups selected from the group consisting of epoxy, carboxylic acid, hydroxy, amide, oxazoline, aceto acetate, methylol, methylol ether, isocyanate, carbamate, amine, amine salt, quaternized amine, thioether, sulfide, sulfonium salt, and phosphate.
62. The thermosetting composition of claim 45, wherein the acceptor monomer composition comprises one or more selected from the group consisting of methyl acrylate, ethyl acrylate, butyl acrylate, isobutyl acrylate, isobornyl acrylate, 2-ethyl hexyl acrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, acrylic acid, dimethylaminoethyl acrylate, acrylamide, chlorotrifluoro ethylene, glycidyl acrylate, and n-butoxy methyl acrylamide.
63. The thermosetting composition of claim 61, wherein the acrylic monomers containing functional groups are one or more selected from the group consisting of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, hydroxypropyl methacrylate, acrylic acid, methacrylic acid, acrylamide, methacrylamide, 2-carbamoyloxyethyl acrylate, 2-carbamoyloxyethyl methacrylate, 2-carbamyloyloxypropryl acrylate, 2-carbamyloyloxypropryl methacrylate, glycidyl acrylate, glycidyl methacrylate, 2-isocyanatoethyl acrylate, 2-isocyanatoethyl methacrylate, 2-isocyanatopropyl acrylate, 2-isocyanatopropyl methacrylate, 2-oxazoline ethyl acrylate, 2-oxazoline ethyl methacrylate, 2-oxazoline propyl acrylate, 2-oxazoline propyl methacrylate, aceto acetate ester of hydroxyethyl acrylate, aceto acetate ester.of hydroxyethyl methacrylate, aceto acetate ester of hydroxypropyl methacrylate, aceto acetate ester of hydroxypropyl acrylate, 2-carbamyloyloxypropryl acrylate, and 2-carbamyloyloxypropryl methacrylate.
64. A method of coating a substrate comprising:
(A) applying a thermosetting composition to the substrate;
(B) coalescing said thermosetting composition to form a substantially continuous film; and (C) curing the thermosetting composition, wherein the thermosetting composition comprises:
(i) a copolymer composition comprising segments comprised of alternating residues derived from a donor monomer composition comprising one or more monomers selected from the group consisting of isobutylene, diisobutylene, dipentene, isoprenone, and an acceptor monomer composition comprising acrylic monomers, and monomers containing functional groups, wherein said copolymer composition is substantially free of transition metals, Lewis acids, maleate-type monomer residues, and fumarate-type monomer residues; and (ii) a crosslinking agent having at least two functional groups that are reactive with the functional groups of the copolymer in (i).
65. The method of claim 64, wherein the thermosetting composition is a liquid solution mixture of (a) and (b).
66. The method of claim 64, wherein the thermosetting composition is a solid particulate mixture of (a) and (b).
67. The method of claim 64, wherein the copolymer (i) in the thermosetting composition has a number average molecular weight of from 500 to 16,000 and a polydispersity index of less than 4.
68. The method of claim 64, wherein the acceptor monomer composition of the copolymer (i) further comprises up to 25 mol % of acrylonitrile.
69. The method of claim 64, wherein the acrylic monomers in the copolymer (i) are 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 and aralkyl, linear or branched C1 to C20 fluoroalkyl, fluoroaryl and fluoroaralkyl, a siloxane, a polysiloxane, an alkyl siloxane, an ethoxylated trimethylsilyl siloxane and a propoxylated trimethylsilyl siloxane, and R5 is a divalent linear or branched C1 to C20 alkyl linking group.
70. The method of claim 64, wherein the monomers containing functional groups of the copolymer (i) have structure (IV):
wherein R10 is H or C1-C4 alkyl and Y represents at least one group selected from the group consisting of C1 to C20 alkyl, aryl and aralkyl containing one or more functional groups selected from the group consisting of epoxy, oxirane, carboxylic acid, hydroxy, amide, oxazoline, aceto acetate, isocyanate, carbamate amine, amine salt, quaternized amine, thioether, sulfide, sulfonium salt, and phosphate.
71. The method of claim 69, wherein the acceptor monomer composition comprises one or more selected from the group consisting of methyl acrylate, ethyl acrylate, butyl acrylate, isobutyl acrylate, isobornyl acrylate, and 2-ethyl hexyl acrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, acrylic acid, dimethylaminoethyl acrylate, acrylamide, chlorotrifluoro ethylene, glycidyl acrylate, and n-butoxy methyl acrylamide.
72. The method of claim 70, wherein the acrylic monomers containing functional groups are one or more selected from the group consisting of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, hydroxypropyl methacrylate, acrylic acid, methacrylic acid, acrylamide, methacrylamide, 2-carbamoyloxyethyl acrylate, 2-carbamoyloxyethyl methacrylate, 2-carbamyloyloxypropryl acrylate, 2-carbamyloyloxypropryl methacrylate, glycidyl acrylate, glycidyl methacrylate, 2-isocyanatoethyl acrylate, 2-isocyanatoethyl methacrylate, 2-isocyanatopropyl acrylate, 2-isocyanatopropyl methacrylate, 2-oxazoline ethyl acrylate, 2-oxazoline ethyl methacrylate, 2-oxazoline propyl acrylate, 2-oxazoline propyl methacrylate, aceto acetate ester of hydroxyethyl acrylate, aceto acetate ester of hydroxyethyl methacrylate, aceto acetate ester of hydroxypropyl methacrylate, aceto acetate ester of hydroxypropyl acrylate, 2-carbamyloyloxypropryl acrylate, and 2-carbamyloyloxypropryl methacrylate.
73. The method of claim 64, wherein the copolymer further comprises one or more monomer residues derived from monomers of the general formula V:
wherein R11, R12, and R14 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, R13 is selected from the group consisting of H, C1-C6 alkyl, COOR15, wherein R15 is selected from the group consisting of H, an alkali metal, a C1 to C6 alkyl group, and aryl.
74. The method of claim 64, wherein the monomers containing functional groups in the copolymer (i) have functional groups selected from the group consisting of epoxy, oxirane, carboxylic acid, hydroxy, amide, amine oxazoline, aceto acetate, isocyanate, methylol, methylol ether, and carbamate, wherein the functional groups of the crosslinking agent (b) are reactive with those in the copolymer (i), and wherein the functional groups of the crosslinking agent (b) are selected from the group consisting of epoxy, oxirane, carboxylic acid, hydroxy, polyol, isocyanate, capped isocyanate, amine, aminoplast, methylol, methylol ether, and beta-hydroxyalkylamide.
75. The method of claim 74, wherein the functional group of the monomers containing functional groups is hydroxy and the functional group of the crosslinking agent (b) is a capped polyisocyanate, wherein the capping group of the capped polyisocyanate crosslinking agent is selected from the group consisting of hydroxy functional compounds, 1H-azoles, lactams, ketoximes, and mixtures thereof.
76. The method of claim 75, wherein the capping group is selected from the group consisting of phenol, p-hydroxy methylbenzoate, 1H-1,2,4-triazole, 1H-2,5-dimethyl pyrazole, 2-propanone oxime, 2-butanone oxime, cyclohexanone oxime, e-caprolactam, and mixtures thereof.
77. The method of claim 75, wherein the polyisocyanate of said capped polyisocyanate crosslinking agent is selected from the group consisting of 1-,6-hexamethylene diisocyanate, cyclohexane diisocyanate, .alpha.,.alpha.'-xylylene diisocyanate, .alpha.,.alpha.,.alpha.',.alpha.'-tetramethylxylylene diisocyanate, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane, diisocyanato-dicyclohexylmethane, dimers of said polyisocyanates, timers of said polyisocyanates, and mixtures thereof.
78. The method of claim 64, wherein the functional polymer has a functional group equivalent weight of from 100 to 5,000 grams / equivalent.
79. The method of claim 64, wherein the equivalent ratio of functional group equivalents in the crosslinking agent to functional group equivalents in the functional copolymer is within the range of 1:3 to 3:1.
80. The method of claim 64, wherein the crosslinking agent is present in an amount of from 1 to 45 percent by weight, based on total weight of resin solids, and the functional copolymer is present in an amount of from 55 to 99 percent by weight, based on total weight of resin solids.
81. The method of claim 74, wherein the monomers containing functional groups contain epoxy functional groups and the crosslinking agent (b) is a carboxylic acid functional compound having from 4 to 20 carbon atoms.
82. The method of claim 81, wherein the carboxylic acid crosslinking agent is selected from the group consisting of dodecanedioic acid, azelaic acid, adipic acid, 1,6-hexanedioic acid, succinic acid, pimelic acid, sebacic acid, maleic acid, citric acid, itaconic acid, aconitic acid, and mixtures thereof.
83. The method of claim 74, wherein the monomers containing functional groups contain carboxylic acid functional groups and the crosslinking agent (b) is a beta-hydroxyalkylamide compound.
84. The method of claim 83, further comprising a second polycarboxylic acid functional material selected from the group consisting of C4 to C20 aliphatic carboxylic acids, polymeric polyanhydrides, polyesters, polyurethanes, and mixtures thereof.
85. The method of claim 83, wherein the beta-hydroxyalkylamide is represented by the following formula:

wherein R24 is H or C1-C5 alkyl, R25 is H, C1-C5 alkyl or for which R24 is as described above, E is a chemical bond or monovalent or polyvalent organic radical derived from saturated, unsaturated, or aromatic hydrocarbon radicals including substituted hydrocarbon radicals containing from 2 to 20 carbon atoms, m is 1 or 2, n is from 0 to 2, and m+n is at least 2.
86. A method of electrocoating a conductive substrate serving as a cathode in an electrical circuit comprising said cathode and an anode, said cathode and anode being immersed in an aqueous electrocoating composition, comprising passing electric current between said cathode and anode to cause deposition of the electrocoating composition on the substrate as a substantially continuous film, the aqueous electrocoating composition comprising:
(a) an ungelled copolymer composition comprising segments comprising alternating residues derived from a donor monomer composition comprising one or more monomers selected from the group consisting of isobutylene, diisobutylene, dipentene and isoprenol, and an acceptor monomer composition comprising acrylic monomers, and residues from monomers containing functional groups which include functional monomers with a functional group containing one or more active hydrogen groups and residues from monomers containing salt groups, wherein said ungelled copolymer composition is substantially free of transition metals, Lewis acids, maleate-type monomer residues, and fumarate-type monomer residues; and (b) a curing agent having at least two functional groups which are reactive with the active hydrogen groups of (a).
87. The method of claim 86, wherein the active hydrogen group-containing copolymer has a number average molecular weight in the range of from 1,000 to 30,000.
88. The method of claim 86, wherein the salt groups of the copolymer are onium salt groups and the copolymer has an onium salt group equivalent weight of from 1,000 to 15,000 grams/equivalent.
89. The method of claim 86, wherein the acceptor monomer composition in the copolymer (a) further comprises up to 25 mol % of acrylonitrile.
90. The method of claim 86, wherein the acrylic monomers in the copolymer (a) are 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), glycidyl, linear or branched C1 to C20 alkyl, alkylol, aryl and aralkyl, linear or branched C1 to C20 fluoroalkyl, fluoroaryl and fluoroaralkyl, a siloxane, a polysiloxane, an alkyl siloxane, an ethoxylated trimethylsilyl siloxane and a propoxylated trimethylsilyl siloxane, and R5 is a divalent linear or branched C1 to C20 alkyl linking group.
91. The method claim 86, wherein the monomers containing active hydrogen groups in the copolymer (a) have structure (IV):
wherein R10 is H or C1-C4 alkyl and Y represents at least one group selected from the group consisting of C1 to C20 alkyl, aryl and aralkyl containing one or more functional groups selected from the group consisting of carboxylic acid, hydroxy, amide, amine, and carbamate.
92. The method claim 90, wherein the acrylic monomer is one or more selected from the group consisting of methyl acrylate, ethyl acrylate, butyl acrylate, isobutyl acrylate, isobornyl acrylate, glycidyl acrylate, 2-ethyl hexyl acrylate acrylamide, acrylic acid, hydroxyethyl acrylate, and hydroxypropyl acrylate.
93. The method of claim 91, wherein the acrylic monomers containing active hydrogen groups are one or more selected from the group consisting of hydroxy ethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, acrylic acid, methacrylic acid, acrylamide, methacrylamide, 2-carbamoyloxyethyl acrylate, 2-carbamoyloxyethyl methacrylate, 2-carbamyloyloxypropryl acrylate, and 2-carbamyloyloxypropryl methacrylate.
94. The method of claim 86, wherein the copolymer further comprises one or more monomer residues derived from monomers of the general formula V:

wherein R11, R12, and R14 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; R13 is selected from the group consisting of H, C1-C6 alkyl, COOR15, wherein R15 is selected from the group consisting of H, an alkali metal, a C1 to C6 alkyl group, glycidyl and aryl.
95. The method claim 86, wherein the monomers containing active hydrogen groups in the copolymer (a) have functional groups selected from the group consisting of carboxylic acid, hydroxy, amide, amine, methylol and carbamate, wherein the functional groups of the curing agent (b) are reactive with those in the copolymer (a), and wherein the functional groups of the curing agent (b) are selected from the group consisting of epoxy, carboxylic acid, hydroxy, polyol, isocyanate, capped isocyanate, amine, methylol, methylol ether, aminoplast, and beta-hydroxyalkylamide.
96. The method of claim 95, wherein the functional group of the monomers containing active hydrogen groups is hydroxy and the functional group of the curing agent (b) is a capped polyisocyanate, wherein the capping group of the capped polyisocyanate crosslinking agent is selected from the group consisting of hydroxy functional compounds, 1H-azoles, lactams, ketoximes, and mixtures thereof.
97. The method of claim 96, wherein the.capping group is selected from the group consisting of phenol, p-hydroxy methylbenzoate, 1H-1,2,4-triazole, 1H-2,5-dimethyl pyrazole, 2-propanone oxime, 2-butanone oxime, cyclohexanone oxime, e-caprolactam, and mixtures thereof.
98. The method of claim 96, wherein the polyisocyanate of said capped polyisocyanate curing agent is selected from the group consisting of 1,6-hexamethylene diisocyanate, cyclohexane diisocyanate, .alpha.,.alpha.'-xylylene diisocyanate, .alpha.,.alpha.,.alpha.',.alpha.'-tetramethylxylylene diisocyanate, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane, diisocyanato-dicyclohexylmethane, dimers of said polyisocyanates, trimers of said polyisocyanates, and mixtures thereof.
99. The method of claim 86, wherein the functional copolymer has a functional group equivalent weight of from 100 to 5,000 grams / equivalent.
100. The method of claim 86, wherein the equivalent ratio of functional group equivalents in the curing agent to functional group equivalents in the functional copolymer is within the range of 1:3 to 3:1.
101. The method of claim 86, wherein the curing agent is present in an amount of from 1 to 45 percent by weight, based on total weight of resin solids, and the functional copolymer is present in an amount of from 55 to 99 percent by weight, based on total weight of resin solids.
102. The method of claim 95, wherein the monomers containing active hydrogen groups contain carboxylic acid functional groups and the curing agent (b) is a beta-hydroxyalkylamide compound.
103. The method of claim 102, further comprising a second polycarboxylic acid functional material selected from the group consisting of C4 to C20 aliphatic carboxylic acids, polymeric polyanhydrides, polyesters, polyurethanes, and mixtures thereof.
104. The method of claim 102, wherein the beta-hydroxyalkylamide is represented by the following formula:
wherein R24 is H or C1-C5 alkyl, R25 is H, C1-C5 alkyl or for which R24 is as described above, E is a chemical bond or monovalent or polyvalent organic radical derived from saturated, unsaturated, or aromatic hydrocarbon radicals including substituted hydrocarbon radicals containing from 2 to 20 carbon atoms, m is 1 or 2, n is from 0 to 2, and m+n is at least 2.
105. The method of claim 86, wherein the salt is an onium salt and said onium salt functional monomers are selected from at least one of the class consisting of quaternary ammonium salts and ternary sulfonium salts.
106. The method of claim 105, wherein the onium salt functional monomers include one or more selected from the group consisting of an epoxy group-containing ethylenically unsaturated monomer which after polymerization has been post-reacted with an amine acid salt and an acid salt of dimethyl aminoethyl (meth)acrylate.
107. The method of claim 105, wherein the onium salt functional monomers are derived from at least one epoxy group-containing monomer which after polymerization has been post-reacted with a sulfide in the presence of an acid.
108. The method of claim 86 wherein the copolymer is a substantially linear polymer having a number average molecular weight in the range of from 1,000 to 30,000, and wherein the salt is an onium salt from an onium salt functional monomer, derived from at least one epoxy group-containing monomer which after polymerization has been post-reacted with an amine acid salt;
the monomers containing active hydrogen groups are at least one hydroxy-alkyl acrylate or hydroxy alkyl methacrylate having 1 to 4 carbon atoms in the alkyl group;
and the acceptor monomer composition includes at least one acrylate monomer.
109. The method of claim 86 wherein component (a) is present in an amount ranging from 25 to 99 weight percent, and component (b) is present in an amount ranging from 1 to 75 weight percent, wherein the weight percentages are based on the total weight of (a) and (b).
110. A substrate coated using the method of claim 64.
111. A substrate coated using the method of claim 65.
112. A substrate coated using the method of claim 66.
113. A substrate coated using the method of claim.86.
114. A multi-component composite coating composition comprising:

(a) a base coat deposited from a pigmented film-forming composition; and (b) a transparent top coat applied over said base coat, wherein said transparent top coat is deposited from a clear film-forming thermosetting composition comprising:
(i) a copolymer composition comprising segments comprised of alternating residues derived from a donor monomer composition comprising one or more monomers selected from the group consisting of isobutylene, diisobutylene, dipentene, isoprenone, and an acceptor monomer composition comprising acrylic monomers, and monomers containing functional groups, wherein said copolymer composition is substantially free of transition metals, Lewis acids, maleate-type monomer residues, and fumarate-type monomer residues; and (ii) a crosslinking agent having at least two functional groups that are reactive with the functional groups of the copolymer in (a).
115. The multi-component composite coating composition of claim 114, wherein the clear thermosetting composition is a liquid solution mixture of (i) and (ii).
116. The multi-component composite coating composition of claim 114, wherein the clear thermosetting composition is a solid particulate mixture of (i) and (ii).
117. A multi-component composite coating composition comprising:
(a) a base coat deposited from a pigmented film-forming composition, wherein said base coat is deposited from a pigmented film-forming thermosetting composition comprising:
(i) a copolymer composition comprising segments comprised of alternating residues derived from a donor monomer composition comprising one or more monomers selected from the group consisting of isobutylene, diisobutylene, dipentene, isoprenone, and an acceptor monomer composition comprising acrylic monomers, and monomers containing functional groups, wherein said copolymer composition is substantially free of transition metals; Lewis acids, maleate-type monomer residues, and fumarate-type monomer residues; and (ii) a crosslinking agent having at least two functional groups that are reactive with the functional groups of the copolymer in (a); and (b) a transparent top coat applied over said base coat.
118. The multi-component composite coating composition of claim 117, wherein the base coat thermosetting composition is a liquid solution mixture of (i) and (ii).
119. The multi-component composite coating composition of claim 117, wherein the base coat thermosetting composition is a solid particulate mixture of (i) and (ii).
120. A multi-component composite coating composition comprising:
(a) a base coat deposited from a pigmented film-forming composition, wherein said base coat is deposited from a pigmented film-forming thermosetting composition comprising:
(i) a copolymer composition comprising segments comprised of alternating residues derived from a donor monomer composition comprising one or more monomers selected from the group consisting of isobutylene, diisobutylene, dipentene, isoprenone, and an acceptor monomer composition comprising acrylic monomers, and monomers containing functional groups, wherein said copolymer composition is substantially free of transition metals, Lewis acids, maleate-type monomer residues, and fumarate-type monomer residues; and (ii) a crosslinking agent having at least two functional groups that are reactive with the functional groups of the copolymer in (a); and (b) a transparent top coat applied over said base coat, wherein said transparent top coat is deposited from a clear film-forming thermosetting composition comprising:
(i) a copolymer composition comprising segments comprised of alternating residues derived from a donor monomer composition comprising one or more monomers selected from the group consisting of isobutylene, diisobutylene, dipentene, isoprenone, and an acceptor monomer composition comprising acrylic monomers, and monomers containing functional groups, wherein said copolymer composition is substantially free of transition metals, Lewis acids, maleate-type monomer residues, and fumarate-type monomer residues; and (ii) a crosslinking agent having at least two functional groups that are reactive with the functional groups of the copolymer in (a).
121. The multi-component composite coating composition of claim 120, wherein the clear thermosetting composition is a liquid solution mixture of (a)(i) and (a)(ii).
122. The multi-component composite coating composition of claim 120, wherein the clear thermosetting composition is a solid particulate mixture of (a)(i) and (a)(ii).
123. The multi-component composite coating composition of claim 120, wherein the base coat thermosetting composition is a liquid solution mixture of (b)(i) and (b)(ii).
124. The multi-component composite coating composition of claim 120, wherein the base coat thermosetting composition is a solid particulate mixture of (b)(i) and (b)(ii).
125. A substrate coated with the multi-component composite coating composition of claim 114.
126. A substrate coated with the multi-component composite coating composition of claim 117.
127. A substrate coated with the multi-component composite coating composition of claim 120.
128. A multi-component composite coating composition comprising:
(a) a primer coat deposited by electrocoating a conductive substrate serving as a cathode in an electrical circuit comprising said cathode and an anode, said cathode and anode being immersed in an aqueous electrocoating composition, comprising passing electric current between said cathode and anode to cause deposition of the electrocoating composition on he substrate as a substantially continuous film;
(b) a base coat deposited from a pigmented film-forming composition; and (c) a transparent top coat applied over said base coat, wherein said transparent top coat is deposited from a clear film-forming thermosetting composition comprising:
(i) a copolymer composition comprising segments comprised of alternating residues derived from a donor monomer composition comprising one or more monomers selected from the group consisting of isobutylene, diisobutylene, dipentene, isoprenone, and an acceptor monomer composition comprising acrylic monomers, and monomers containing functional groups, wherein said copolymer composition is substantially free of transition metals, Lewis acids, maleate-type monomer residues, and fumarate-type monomer residues; and (ii) a crosslinking agent having at least two functional groups that are reactive with the functional groups of the copolymer in (i).
129. The multi-component composite coating composition of claim 128, wherein the clear thermosetting composition is a liquid solution mixture of (i) and (ii).
130. The multi-component composite coating composition of claim 128, wherein the clear thermosetting composition is a solid particulate mixture of (i) and (ii).
131. A multi-component composite coating composition comprising:
(a) a primer coat deposited by electrocoating a conductive substrate serving as a cathode in an electrical circuit comprising said cathode and an anode, said cathode and anode being immersed in an aqueous electrocoating composition, comprising passing electric current between said cathode and anode to cause deposition of the electrocoating composition on the substrate as a substantially continuous film;
(b) a base coat deposited from a pigmented film-forming composition, wherein said base coat is deposited from a pigmented film-forming thermosetting composition comprising:
(i) a copolymer composition comprising segments comprised of alternating residues derived from a donor monomer composition comprising one or more monomers selected from the group consisting of isobutylene, diisobutylene, dipentene, isoprenone, and an acceptor monomer composition comprising acrylic monomers, and monomers containing functional groups, wherein said copolymer composition is substantially free of transition metals, Lewis acids, maleate-type monomer residues, and fumarate-type monomer residues; and (ii) a crosslinking agent having at least two functional groups that are reactive with the functional groups of the copolymer in (i); and (c) a transparent top coat applied over said base coat.
132. The multi-component composite coating composition of claim 131, wherein the base coat thermosetting composition is a liquid solution mixture of (i) and (ii).
133. The multi-component composite coating composition of claim 131, wherein the base coat thermosetting composition is a solid particulate mixture of (i) and (ii).
134. A primed multi-component composite coating composition comprising:
(a) a primer coat deposited by electrocoating a conductive substrate serving as a cathode in an electrical circuit comprising said cathode and an anode, said cathode and anode being immersed in an aqueous electrocoating composition, comprising passing electric current between said cathode and anode to cause deposition of the electrocoating composition on the substrate as a substantially continuous film;
(b) a base coat deposited from a pigmented film-forming composition, wherein said base coat is deposited from a pigmented film-forming thermosetting composition comprising:
(i) a copolymer composition comprising segments comprised of alternating residues derived from a donor monomer composition comprising one or more monomers selected from the group consisting of isobutylene, diisobutylene, dipentene, isoprenone, and an acceptor monomer composition comprising acrylic monomers, and monomers containing functional groups, wherein said copolymer composition is substantially free of transition metals, Lewis acids, maleate-type monomer residues, and fumarate-type monomer residues; and (ii) a crosslinking agent having at least two functional groups that are reactive with the functional groups of the copolymer in (i); and (c) a transparent top coat applied over said base coat, wherein said transparent top coat is deposited from a clear film-forming thermosetting composition comprising:
(i) a copolymer composition comprising segments comprised of alternating residues derived from a donor monomer composition comprising one or more monomers selected from the group consisting of isobutylene, diisobutylene, dipentene, isoprenone, and an acceptor monomer composition comprising acrylic monomers, and monomers containing functional groups, wherein said copolymer composition is substantially free of transition metals, Lewis acids, maleate-type monomer residues, and fumarate-type monomer residues; and (ii) a crosslinking agent having at least two functional groups that are reactive with the functional groups of the copolymer in (a).
135. The multi-component composite coating composition of claim 134, wherein the clear thermosetting composition is a liquid solution mixture of (a)(i) and (a)(ii).
136. The multi-component composite coating composition of claim 134, wherein the clear thermosetting composition is a solid particulate mixture of (a)(i) and (a)(ii).
137. The multi-component composite coating composition of claim 134, wherein the base coat thermosetting-composition is a liquid solution mixture of (b)(i) and (b)(ii).
138. The multi-component composite coating composition of claim 134, wherein the base coat thermosetting composition is a solid particulate mixture of (b) (i) and (b) (ii) .
139. A substrate coated with the multi-component composite coating composition of claim 128.
140. A substrate coated with the multi-component composite coating composition of claim 131.
141. A substrate coated with the multi-component composite coating composition of claim 134.
142. The thermosetting composition of claim 1, wherein the volatile organic compound content is less than 3.5 percent by weight.
143. The method of claim 64, wherein the thermosetting composition has a volatile organic compound component of less than 3.5 percent by weight.
CA 2476090 2002-02-15 2003-01-29 Thermosetting compositions containing alternating copolymers of isobutylene type monomers Expired - Fee Related CA2476090C (en)

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