Patent US4267948A successfully refreshed from Google Patents.
Patent US4870140A successfully refreshed from Google Patents.
US4870140A
Expired / Lapsed
US
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Polyester graft copolymers, flexible coating compositions comprising same and branched polyester macromers for preparing same II
Assignee: EIDP Inc
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Filing: 1988-10-03
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Granted: 1989-09-26
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Expires: 2008-10-03
Abstract
Abstract 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 1300 and about 15,000, has a hydroxyl 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 macromer. The macromer is the reaction product of (i) hydroxy functional polyester reactant containing 0-10 urethane linkages per molecule with (ii) silane compound having the general chemical formula: ##STR1## wherein X is an organic group or (--Si--O--) n , n being 1-50, and X' is indedpendently an organic group, hydroxy-reactive functionality, or an organic group comprising hydroxy-reactive functionality, at least one X' comprising hydroxy-reactive functionality.
Inventors
- 👤 Rose A. Ryntz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 19:47
CPC Classifications
C; C08; C08F; C08F299/00; C08F299/02; C08F299/06; C08F299/04; C08F299/0485; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/42; C08G18/4266; C08G18/4286; C08G18/83; C08G18/837; C08G63/00; C08G63/68; C08G63/695; C09; C09D; C09D167/00; C09D167/06
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
184 words
A solvent based coating composition comprising: (A) hydroxy functional polyester urethane graft copolymer having a number average molecular weight between about 1,300 and about 15,000, having a hydroxyl number between about 30 and about 300, and consisting of the reaction product of carbon-carbon double bond-reactive monoethylenically unsaturated monomer with hydroxy functional carbon-carbon double bond-bearing branched polyester urethane macromer, under free radical polymerization reaction conditions, said monomer bearing substantially no functionality which is substantially reactive with hydroxy functionality of said macromer under said reaction conditions, said macromer consists of the reaction product of (i) hydroxy functional polyester urethane having about 1-10 urethane groups per molecule with (ii) silane compound having the general chemical formula: ##STR6## wherein X is an organic group or (--Si--O--) n , n being 1-50 , and X' is independently (a) an organic group, (b) an organic group comprising hydroxy-reactive functionality or (c) hydroxy-reactive functionality, at least one X' comprising hydroxy-reactive functionality; said polyester urethane consists of the hydroxyl terminated esterification product of a polyol and a dicarboxylic acid or anhydride thereof and an organic diisocyanate and (B) polyfunctional, hydroxy-reactive crosslinking agent.
Claim 2
Dependent Claim
184 words
A solvent based coating composition comprising: (A) hydroxy functional polyester urethane graft copolymer having a number average molecular weight between about 1,300 and about 15,000, having a hydroxyl number between about 30 and about 300, and consisting of the reaction product of carbon-carbon double bond-reactive monoethylenically unsaturated monomer with hydroxy functional carbon-carbon double bond-bearing branched polyester urethane macromer, under free radical polymerization reaction conditions, said monomer bearing substantially no functionality which is substantially reactive with hydroxy functionality of said macromer under said reaction conditions, said macromer consists of the reaction product of (i) hydroxy functional polyester urethane having about 1-10 urethane groups per molecule with (ii) silane compound having the general chemical formula: ##STR6## wherein X is an organic group or (--Si--O--) n , n being 1-50 , and X' is independently (a) an organic group, (b) an organic group comprising hydroxy-reactive functionality or (c) hydroxy-reactive functionality, at least one X' comprising hydroxy-reactive functionality; said polyester urethane consists of the hydroxyl terminated esterification product of a polyol and a dicarboxylic acid or anhydride thereof and an organic diisocyanate and (B) polyfunctional, hydroxy-reactive crosslinking agent.
Claim 3
Dependent Claim
86 words
The solvent based coating composition of claim 1, wherein said polyfunctional, hydroxy-reactive crosslinking agent is selected from polyisocyanate crosslinking agent and blocked polyisocyanate crosslinking agent comprising at least two isocyanate groups blocked by reaction with active hydrogen bearing blocking agent, and a compatible mixture of any of them, said crosslinking agent being included in an amount sufficient to provide, at a cure temperature of said composition, between about 0.5 and about 1.6 hydroxy reactive groups per hydroxy group present on said hydroxy functional polyester graft copolymer.
Claim 4
Dependent Claim
43 words
The solvent based coating composition of claim 1, wherein said polyfunctional, hydroxy-reactive crosslinking agent is melamine based crosslinking agent, said crosslinking agent being included in said composition in an amount between about 5% and about 60% by weight of the total resin solids.
Claim 5
Dependent Claim
157 words
A solvent based, one component, high solids enamel topcoat comprising: (A) hydroxy functional polyester urethane graft copolymer having a number average molecular weight about 1,500-3,000, having a hydroxyl number between about 50 and about 150 and about 1-7 urethane linkages per molecule, and being the reaction product of carbon-carbon double bond-reactive monoethylenically unsaturated monomer with carbon-carbon double bond-bearing branched polyester urethane macromer under free radical polymerization reaction conditions, said monomer bearing substantially no functionality which is substantially reactive with hydroxy functionality of said macromer under said reaction conditions, said macromer being the reaction product of silane compound selected from gamma-methacryloxypropyltrimethoxysilane and vinyl triethoxysilane with hydroxy functional oligomeric polyester urethane consisting of the hydroxyl terminated esterification product of a polyol and a dicarboxylic acid or anhydride thereof and an organic diisocyanate; and (B) melamine based crosslinking agent, said crosslinking agent being included in an amount between about 5% and about 60% by weight of the total resin solids.
Claim 6
Dependent Claim
157 words
A solvent based, one component, high solids enamel topcoat comprising: (A) hydroxy functional polyester urethane graft copolymer having a number average molecular weight about 1,500-3,000, having a hydroxyl number between about 50 and about 150 and about 1-7 urethane linkages per molecule, and being the reaction product of carbon-carbon double bond-reactive monoethylenically unsaturated monomer with carbon-carbon double bond-bearing branched polyester urethane macromer under free radical polymerization reaction conditions, said monomer bearing substantially no functionality which is substantially reactive with hydroxy functionality of said macromer under said reaction conditions, said macromer being the reaction product of silane compound selected from gamma-methacryloxypropyltrimethoxysilane and vinyl triethoxysilane with hydroxy functional oligomeric polyester urethane consisting of the hydroxyl terminated esterification product of a polyol and a dicarboxylic acid or anhydride thereof and an organic diisocyanate; and (B) melamine based crosslinking agent, said crosslinking agent being included in an amount between about 5% and about 60% by weight of the total resin solids.
Claim 7
Dependent Claim
27 words
The solvent based coating composition of claim 1, wherein said organic group of said silane compound is selected from cyclic and acylic, alkyl and aryl organic groups.
Claim 8
Dependent Claim
25 words
The solvent based coating composition of claim 1, wherein said hydroxy-reactive functionality of said silane compound is selected from alkoxy, halide, carboxyl, amino and epoxide.
Claim 9
Dependent Claim
22 words
The solvent based coating composition of claim 1, wherein saidd silane compound has a molecular weight between about 100 and about 1000.
Claim 10
Dependent Claim
27 words
The solvent based coating composition of claim 7, wherein said silane compound is selected from the group consisting of gamma-methacryloxypropyl trimethoxysilane, vinyl triethoxysilane and a mixture thereof.
Claim 11
Dependent Claim
25 words
The solvent based coating composition of claim 1, wherein said hydroxy functional polyester urethane and said silane compound are reacted in approximately 1:1 molar ratio.
Claim 12
Dependent Claim
47 words
The solvent based coating composition of claim 1, wherein said carbon-carbon double bond-reactive monoethylenically unsaturated monomer consists of acrylate monomers 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 13
Dependent Claim
48 words
The solvent based coating composition of claim 1, wherein said carbon-carbon double bond-reactive monoethylenically unsaturated monomer consists of monomers 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 14
Dependent Claim
29 words
The solvent based coating composition of claim 1, wherein said dicarboxylic acid is selected from the group consisting of substantially saturated, acyclic, aliphatic dimer acids of about 6-36 carbons.
Claim 15
Dependent Claim
34 words
The solvent based coating composition of claim 1, 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 16
Dependent Claim
26 words
The solvent based coating composition of claim 1, wherein said polyol comprises diol and triol in hydroxy equivalent ratio of from about 4:1 to about 1:4.
Claim 17
Dependent Claim
26 words
The solvent based coating composition of claim 14, wherein said triol is selected from thr groups consisting of trimethylol propane, polycaprolactone triol, and any mixture thereof.
Claim 18
Dependent Claim
33 words
The solvent based 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
49 words
The solvent based coating composition of claim 16, 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
28 words
The solvent based coating composition of claim 14, wherein said diol is selected from the group consisting of alkyl glycol of about 2-7 carbons, and any mixture thereof.
Claim 21
Dependent Claim
48 words
The solvent based coating composition of claim 18, 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 22
Dependent Claim
69 words
The solvent based coating composition of claim 1, wherein said hydroxy functional polyester urethane consists of the reaction product of organic diisocyanate with the reaction product if dicarboxylic acid with polyol comprising at least about 5 percent by weight triol, said dicarboxylic acid being selected from the group consisting of saturated and unsaturated, cyclic and acyclic aliphatic dicarboxylic acids, aromatic dicarboxylic acids, suitable anhydrides thereof, and any mixture thereof.
Claim 23
Dependent Claim
26 words
The solvent based coating composition of claim 11, wherein said hydroxy reactive functionality of said silane compound is selected from alkoxy, halide, carboxyl, amino and epoxide.
Claim 24
Dependent Claim
29 words
The solvent based coating composition of claim 20, wherein said dicarboxylic acid is selected from the group consisting of substantially saturated, acyclic, aliphatic dimer acids of about 6-36 carbons.
Claim 25
Dependent Claim
32 words
The solvent based coating composition of claim 20, wherein said dicarboxylic acid is selected from the group consisting of adipic acid, azelaic acid, sebasic acid, dodecane dicarboxylic acid and any mixture thereof.
Claim 26
Dependent Claim
26 words
The solvent based coating composition of claim 20, wherein said polyol comprises diol and triol in hydroxy equivalent ratio of from about 4:1 to about 1:4.
Claim 27
Dependent Claim
47 words
The solvent based coating composition of claim 24, 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 28
Dependent Claim
26 words
The solvent based coating composition of claim 24, wherein said triol is selected from the group consisting of trimethylol propane, polycaprolactone triol, and any mixture thereof.
Claim 29
Dependent Claim
48 words
The solvent based coating composition of claim 20, wherein said diisocyanate is selected from the group consisting of phenyl 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.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-09-25 | 1993-03-27 | 1993-09-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-09-25 | 1997-03-27 | 1997-09-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-09-25 | 2001-03-27 | 2001-09-26 | $7700.00 | Window Closed / Lapsed |