US4952626A
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US
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Polyester graft copolymers, flexible coating compositions comprising same and branched polyester macromonomers for preparing same - II
Assignee: EIDP Inc
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Filing: 1988-12-09
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Granted: 1990-08-28
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Expires: 2008-12-09
Abstract
Abstract Coating composition containing hydroxy functional polyester graft copolymers are provided. The copolymer is crosslinkable by hydroxy-reactive crosslinking agent and, in particular, is suitable for use in thermosetting coating compositions adapted to form a flexible cured coating over a variety of substrates, such as metal and plastic. The copolymer has a number average molecular weight between about 1,300 and about 15,000, has a hydroxy number between about 30 and about 300, and is the reaction product of carbon-carbon double bond-reactive monoethylenically unsaturated monomer with hydroxy functional carbon-carbon double bond-bearing branched polyester macromonomer. The macromonomer is the reaction product of (i) isocyanato monomer having the formula: ##STR1## with (ii) hydroxy functional polyester reactant containing 0-1- urethane linkages per molecule.
Inventors
- 👤 Panagiotis I. Kordomenos
- 👤 Rose A. Ryntz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 03:52
CPC Classifications
C; C09; C09D; C09D167/00; C08; C08F; C08F299/00; C08F299/02; C08F299/04; C08F299/0485; C08F299/0492; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/81; C08G18/8108; C08G18/8141; C08G18/815; C08G18/8158; C08G18/8175; C09D155/00; C09D155/005
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
160 words
Thermosetting, flexible, solvent-based coating composition comprising a hydroxy functional polyester graft copolymer and a hydroxy-reactive crosslinking agent, wherein the hydroxy functional graft copolymer has number average molecular weight between about 1,300 and 15,000, has a hydroxyl number between about 30 and 300, and is the reaction product of carbon-carbon double bond-reactive monoethylenically unsaturated monomer with hydroxy functional carbon-carbon double bond-bearing branched polyester macromonomer, under free radical polymerization reaction conditions, said monomer bearing substantially no functionality which is substantially reactive with hydroxy functionality of said macromonomer under said reaction conditions and said macromonomer being the reaction product of (i) isocyanato monomer having the formula: ##STR6## wherein R is hydrogen or C 1 to about C 7 alkyl, and R' is a divalent hydrocarbon linking moiety which does not substantially interfere with the reactivity of either the isocyanate group or the ethylenic double bond of said isocyanato monomer with (ii) hydroxy functional saturated polyester reactant having about 0-10 urethane groups per molecule.
Claim 2
Dependent Claim
160 words
Thermosetting, flexible, solvent-based coating composition comprising a hydroxy functional polyester graft copolymer and a hydroxy-reactive crosslinking agent, wherein the hydroxy functional graft copolymer has number average molecular weight between about 1,300 and 15,000, has a hydroxyl number between about 30 and 300, and is the reaction product of carbon-carbon double bond-reactive monoethylenically unsaturated monomer with hydroxy functional carbon-carbon double bond-bearing branched polyester macromonomer, under free radical polymerization reaction conditions, said monomer bearing substantially no functionality which is substantially reactive with hydroxy functionality of said macromonomer under said reaction conditions and said macromonomer being the reaction product of (i) isocyanato monomer having the formula: ##STR6## wherein R is hydrogen or C 1 to about C 7 alkyl, and R' is a divalent hydrocarbon linking moiety which does not substantially interfere with the reactivity of either the isocyanate group or the ethylenic double bond of said isocyanato monomer with (ii) hydroxy functional saturated polyester reactant having about 0-10 urethane groups per molecule.
Claim 3
Dependent Claim
97 words
The coating composition of claim 1, wherein said divalent hydrocarbon linking moiety, R', of said isocyanato monomer is C 1 to about C 7 alkylene, COO(CH 2 ) n , n being 1 to about 7, CH(CH 3 )C 6 H 4 C(CH 3 ) 2 or COO(CH 2 ) m OCONHC 6 Hx--Q y' , m being 1 to about 7, x and y together equaling 6 and each Q being any substituent group which does not substantially interfere with the reactivity of either the isocyanate group or the ethylenic double bond of said isocyanato monomer.
Claim 4
Dependent Claim
35 words
The coating composition of claim 2, wherein R is selected from H and CH 3 and in said divalent linking moiety, R', the variable y is 1 and said substituent Q is CH 3 .
Claim 5
Dependent Claim
29 words
The coating composition of claim 1, wherein said isocyanato monomer is selected from the group consisting of isocyanato ethyl methacrylate, isocyanato propyl methacrylate, 1-(1-isocyanato-1-methylethyl)-3-(1-methylethenyl)-benzene, and any compatible mixture thereof.
Claim 6
Dependent Claim
20 words
The coating composition of claim 1, wherein said isocyanato monomer is the reaction product of hydroxy alkyl acrylate with diisocyanate.
Claim 7
Dependent Claim
17 words
The coating composition of claim 5, wherein said hydroxy alkyl acrylate consists essentially of hydroxy ethyl acrylate.
Claim 8
Dependent Claim
24 words
The coating composition of claim 5, wherein said diisocyanate is selected from the group consisting of isophorone diisocyanate, 2,4-toluene diisocyanate and any mixture thereof.
Claim 9
Dependent Claim
24 words
The coating composition of claim 1, wherein said isocyanato monomer and said hydroxy functional saturated polyester reactant are reacted in approximately 1:1 molar ratio.
Claim 10
Dependent Claim
42 words
The coating composition of claim 1, wherein said carbon-carbon double bond-reactive monoethylenically unsaturated monomer is selected from the group consisting of alkylacrylate, alkyl methacrylate, hydroxyalkylacrylate, hydroxyalkyl methacrylate and mixtures thereof, wherein each alkyl and hydroxyalkyl moiety has one to about seven carbons.
Claim 11
Dependent Claim
44 words
The coating composition of claim 1, wherein said carbon-carbon double bond-reactive monoethylenically unsaturated monomer is selected from the group consisting of acrylic acid, methacrylic acid, styrene, methylacrylate, ethylacrylate, propylacrylate, butylacrylate, methylmethacrylate, ethylmethacrylate, propylmethacrylate, butylmethacrylate, hydroxyethylacrylate, hydroxypropylacrylate, hydroxybutylacrylate, hydroxyethylmethacrylate, hydroxypropylmethacrylate, hydroxybutylmethacrylate, and any mixture thereof.
Claim 12
Dependent Claim
58 words
The coating composition of claim 1 wherein said hydroxy functional saturated polyester reactant comprises the reaction product of dicarboxylic acid with polyol comprising at least about 5 percent by weight triol, said dicarboxylic acid being selected from the group consisting of saturated, cyclic, and acyclic aliphatic dicarboxylic acids and aromatic dicarboxylic acids, suitable anhydrides thereof, and mixtures thereof.
Claim 13
Dependent Claim
29 words
The coating composition of claim 11, wherein said dicarboxylic acid is selected from the group consisting of substantially saturated, acyclic, aliphatic dimer acids of about 6 to 36 carbons.
Claim 14
Dependent Claim
32 words
The coating composition of claim 11, wherein said dicarboxylic acid is selected from the group consisting of adipic acid, azelaic acid, sebasic acid, dodecane dicarboxylic acid, phthalic anhydride and any mixture thereof.
Claim 15
Dependent Claim
24 words
The coating composition of claim 11, wherein said polyol comprises diol and triol in hydroxy equivalent ratio of from about 4:1 to about 1:4.
Claim 16
Dependent Claim
45 words
The coating composition of claim 14, wherein said diol has molecular weight of about 60-500 and is selected from the group consisting of trimethylene glycol, triethylene glycol, 1,4-cyclohexane dimethanol, alkyl substituted or unsubstituted propanediol, butanediol, pentanediol and hexanediol, and a mixture of any of them.
Claim 17
Dependent Claim
24 words
The coating composition of claim 14, wherein said triol is selected from the groups consisting of trimethylol propane, polycaprolactone triol, and any mixture thereof.
Claim 18
Dependent Claim
31 words
The coating composition of claim 14, wherein said diol is aliphatic diol of the general formula HO--R"--OH, wherein R" is a divalent, aliphatic, linking moiety substantially unreactive with said dicarboxylic acid.
Claim 19
Dependent Claim
47 words
The coating composition of claim 17, wherein said aliphatic diol has a molecular weight of about 60-500 and is selected from the group consisting of trimethylene glycol, triethylene glycol, 1,4-cyclohexane dimethanol, alkyl substituted or unsubstituted propanediol, butanediol, pentanediol and hexanediol, and a mixture of any of them.
Claim 20
Dependent Claim
26 words
The coating composition of claim 14, wherein said diol is selected from the group consisting of alkylene glycol of about 2-7 carbons, and any mixture thereof.
Claim 21
Dependent Claim
28 words
The coating composition of claim 11, wherein said hydroxy functional saturated polyester reactant is urethane modified, said polyol comprising the reaction product of organic diisocyanate with polyhydroxy reactant.
Claim 22
Dependent Claim
46 words
The coating composition of claim 20, wherein said diisocyanate is selected from the group consisting of phenylene diisocyanate, biphenyl diisocyanate, toluene diisocyanate, isophorone diisocyanate, 3,3'-dimethyl-4,4'-biphenylene diisocyanate, diisocyanatoalkane wherein the alkane moiety has about three to about ten carbons, and a compatible mixture of any of them.
Claim 23
Dependent Claim
68 words
The coating composition of claim 1, wherein said hydroxy functional saturated polyester reactant is urethane modified, comprising the reaction product of organic diisocyanate with the reaction product of dicarboxylic acid with polyol comprising at least about 5 percent by weight triol, said dicarboxylic acid being selected from the group consisting of saturated cyclic and acyclic aliphatic dicarboxylic acids, aromatic dicarboxylic acids, suitable anhydrides thereof, and any mixture thereof.
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