Patent US3953389A successfully refreshed from Google Patents.
Patent US4296215A successfully refreshed from Google Patents.
US4296215A
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US
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Method to thicken dissolved thermoset resins
Assignee: Beazer East Inc
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Filing: 1980-04-07
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Granted: 1981-10-20
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Expires: 2000-04-07
Abstract
Abstract Dissolved or dispersed thermoset resins compositions which have a molecular weight of at least 500 may be thickened by the addition of a polyfunctional isocyanate and a trimerization catalyst. The thickened compositions can be cured by a free radical catalyst and the application of heat and/or pressure. A variety of reinforced articles can be produced from the thickened compositions.
Inventors
- 👤 Kenneth H. Markiewitz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 03:47
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/09; C08G18/092; C08G18/04; C08L; C08L75/00; C08L75/04; C08L75/14; C08L75/16; Y; Y10; Y10S; Y10S525/00; Y10S525/92; Y10S525/922
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
127 words
A method of increasing the viscosity of a uniformly dispersed or solubilized composition comprising (A) at least 10 percent by weight of a polymerizable resin selected from the class consisting of a vinyl urethane resin and an unsaturated polyester resin which resin is curable to a thermoset resin and has a molecular weight of at least 500, and (B) up to 90% by weight of an ethylenically unsaturated monomer, which method comprises mixing into the composition an amount of at least 2% by weight of the composition of a polyisocyanate and a catalytic amount of a trimerization catalyst selected from the class consisting of quaternary ammonium hydroxides, quaternary ammonium acetates, quaternary ammonium formates, alkali metal acetates and alkali metal formates, and trimerizing the polyisocyanate in the composition.
Claim 2
Independent Claim
127 words
A method of increasing the viscosity of a uniformly dispersed or solubilized composition comprising (A) at least 10 percent by weight of a polymerizable resin selected from the class consisting of a vinyl urethane resin and an unsaturated polyester resin which resin is curable to a thermoset resin and has a molecular weight of at least 500, and (B) up to 90% by weight of an ethylenically unsaturated monomer, which method comprises mixing into the composition an amount of at least 2% by weight of the composition of a polyisocyanate and a catalytic amount of a trimerization catalyst selected from the class consisting of quaternary ammonium hydroxides, quaternary ammonium acetates, quaternary ammonium formates, alkali metal acetates and alkali metal formates, and trimerizing the polyisocyanate in the composition.
Claim 3
Dependent Claim
32 words
A method as claimed in claim 1 wherein the polymerizable has a hydroxyl number of less than 30 and is dissolved or dispersed in up to 75% by weight of the composition.
Claim 4
Dependent Claim
24 words
A method as claimed in claim 1 wherein the polyisocyanate is added in an amount of 2 to 10% by weight of the composition.
Claim 5
Dependent Claim
21 words
A method as claimed in claim 1 wherein the composition is thickened to a viscosity of at least one million centipoise.
Claim 6
Dependent Claim
41 words
A method as claimed in claim 1 wherein the polyisocyanate is selected from the group consisting of 2,4-toluene diisocyanate, diphenyl methane diisocyanate, 2,6-toluene diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, 4,4'-diphenyl ether diisocyanate, diphenylmethane polyisocyanate having 2.1 to 3.0 isocyanate groups per mol.
Claim 7
Dependent Claim
47 words
A method as claimed in claim 1 wherein the monomer is a monomer selected from the group consisting of styrene, vinyltoluene, divinyl benzene, the methyl, ethyl, n-butyl, 2-ethyl hexyl or pentaerythritol esters of acrylic and methacrylic acid, triallyl isocyanurate, vinyl acetate, diallyl fumarate, vinyl ether and acrylonitrile.
Claim 8
Dependent Claim
157 words
A method as claimed in claim 1 wherein the polymerizable resin is an isocyanurate of urethanes of an aromatic polyisocyanate and at least one vinylidene carbonyl oxy alkanol characterized by one of the following formulas: ##STR5## wherein R 1 is hydrogen or an alkyl group containing from 1 to 4 carbon atoms, R 2 is hydrogen, alkyl containing from 1 to 12 carbon atoms, or a chlorinated, brominated, or fluorinated alkyl group containing from 1 to 12 carbon atoms, R 3 is hydrogen, alkyl containing from 1 to 12 carbon atoms, or a chlorinated, brominated, or fluorinated alkyl group containing from 1 to 12 carbon atoms, R 4 is hydrogen, methyl or ethyl, and n is from one to four, with the proviso that R 2 and R 3 on adjacent carbon atoms are not both alkyl or chlorinated, brominated, or fluorinated alkyl, that is at least one of R 2 and R 3 must be hydrogen.
Claim 9
Dependent Claim
195 words
A method as claimed in claim 1 wherein the polymerizable resin has the following formula B--I--A--M].sub.y A--(I--B).sub.q wherein A is a radical derived from a polyoxyalkylene bisphenol A having the following formula: ##STR6## wherein R' is C 1 -C 4 alkylene group, X is halogen or a C 1 -C 4 alkyl group, a is an integer equal to from 0 to 2, and m and n are integers each of which is equal to at least 1 and the sum of which is equal to from 2.0 to about 30.0; M is a radical derived from (A) an unsaturated, aliphatic, polycarboxylic acid or an anhydride thereof, (B) a saturated aliphatic polycarboxylic acid or an anhydride thereof, (C) an aromatic polycarboxylic acid or anhydride thereof or (D) mixture of A, B, or C; I is a radical derived from an isocyanate having an isocyanate functionality of at least 2; B is a radical derived from a monohydroxyl-terminated ester of unsubstituted or substituted acrylic or methacrylic acid wherein the substitutents are halogen or C 1 -C 4 alkyl groups; y is an integer equal to from 1 to about 12, and q is zero or one.
Claim 10
Dependent Claim
14 words
A polymerizable composition which comprises a product produced by the method of claim 1.
Claim 11
Dependent Claim
18 words
A composition as claimed in claim 9 which comprises a product produced by the method of claim 2.
Claim 12
Dependent Claim
27 words
A composition as claimed in claim 10 wherein the polyisocyanate is added in an amount of 4 to 10% by weight of the dispersed or solubilized composition.
Claim 13
Dependent Claim
18 words
A composition as claimed in claim 9 wherein the trimerization catalyst is N-benzyl-trimethyl ammonium hydroxide or potassium acetate.
Claim 14
Dependent Claim
38 words
A composition as claimed in claim 9 wherein the polyisocyanate is selected from the group consisting of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, 4,4'-diphenyl ether diisocyanate, diphenylmethane polyisocyanate, having 2.1 to 3.0 isocyanate groups per mol.
Claim 15
Dependent Claim
47 words
A composition as claimed in claim 9 wherein the monomer is a monomer selected from the group consisting of styrene, vinyltoluene, divinyl benzene, the methyl, ethyl, n-butyl, 2-ethyl hexyl or pentaerythritol esters of acrylic and methacrylic acid, triallyl isocyanurate, vinyl acetate, diallyl fumarate, vinyl ether and acrylonitrile.
Claim 16
Dependent Claim
157 words
A composition as claimed in claim 9 wherein the polymerizable resin is an isocyanurate of urethanes of an aromatic polyisocyanate and at least one vinylidene carbonyl oxy alkanol characterized by one of the following formulas: ##STR7## wherein R 1 is hydrogen or an alkyl group containing from 1 to 4 carbon atoms, R 2 is hydrogen, alkyl containing from 1 to 12 carbon atoms, or a chlorinated, brominated, or fluorinated alkyl group containing from 1 to 12 carbon atoms, R 3 is hydrogen, alkyl containing from 1 to 12 carbon atoms, or a chlorinated brominated, or fluorinated alkyl group containing from 1 to 12 carbon atoms, R 4 is hydrogen, methyl or ethyl, and n is from one to four, with the proviso that R 2 and R 3 on adjacent carbon atoms are not both alkyl or chlorinated, brominated, or fluorinated alkyl, that is at least one of R 2 and R 3 must be hydrogen.
Claim 17
Dependent Claim
195 words
A composition as claimed in claim 9 wherein the polymerizable resin has the following formula: b--I--A--M].sub.y A--(I--B).sub.q wherein A is a radical derived from a polyoxyalkylene bisphenol A having the following formula: ##STR8## wherein R' is C 1 -C 4 alkylene group, X is halogen or a C 1 -C 4 alkyl group, a is an integer equal to from 0 to 2, and m and n are integers each of which is equal to at least 1 and the sum of which is equal to from 2.0 to about 30.0; M is a radical derived from (A) an unsaturated, aliphatic, polycarboxylic acid or an anhydride thereof, (B) a saturated aliphatic polycarboxylic acid or an anhydride thereof, (C) an aromatic polycarboxylic acid or anhydride thereof or (D) mixtures of A, B, or C; I is a radical derived from an isocyanate having an isocyanate functionality of at least 2; B is a radical derived from a monohydroxyl-terminated ester of unsubstituted or substituted acrylic or methacrylic acid wherein the substituents are halogen or C 1 -C 4 alkyl groups; y is an integer equal to from 1 to about 12, and q is zero or one.
Claim 18
Dependent Claim
22 words
A composition as claimed in claim 9 which is a sheet molding composition having a viscosity of more than one million centipoise.
Claim 19
Dependent Claim
17 words
A sheet molding composition as claimed in claim 17 which additionally comprises a reinforcing glass fiber filler.
Claim 20
Dependent Claim
15 words
A composition as claimed in claim 18 which additionally comprises a free radical polymerization catalyst.
Claim 21
Dependent Claim
38 words
A composition as claimed in claim 18 wherein said reinforcing filler is selected from the group consisting of glass fibers, graphite fibers, asbestos fibers, fibers derived from organic polymers, ranging in size from one to 10 cms. long.
Claim 22
Dependent Claim
33 words
A fully cured sheet molded composition made by the process of shaping a composition as claimed in claim 20 and thereafter copolymerizing the ethylenically unsaturated monomer with said thermoset resin by free-radical activation.
Claim 23
Dependent Claim
115 words
A resin blend useful in preparing nontacky molding compositions by the reaction therewith of polyisocyanates which comprises: (1) At least 10% by weight of the blend of the polymerizable resin selected from the class consisting of a vinyl urethane resin and a unsaturated polyester resin, which polymerizable resins has a molecular weight of at least 500 and which is curable to a thermoset resin. (2) Up to 90% by weight of the blend, of a ethylenically unsaturated monomer. (3) From 0.002 to 1% by weight of the blend of a polyisocyanate trimerization catalyst selected from the class consisting of quaternary ammonium hydroxide, quaternary ammonium acetates, quaternary ammonium formates, alkali metal acetates and alkali metal formates.
Claim 24
Dependent Claim
115 words
A resin blend useful in preparing nontacky molding compositions by the reaction therewith of polyisocyanates which comprises: (1) At least 10% by weight of the blend of the polymerizable resin selected from the class consisting of a vinyl urethane resin and a unsaturated polyester resin, which polymerizable resins has a molecular weight of at least 500 and which is curable to a thermoset resin. (2) Up to 90% by weight of the blend, of a ethylenically unsaturated monomer. (3) From 0.002 to 1% by weight of the blend of a polyisocyanate trimerization catalyst selected from the class consisting of quaternary ammonium hydroxide, quaternary ammonium acetates, quaternary ammonium formates, alkali metal acetates and alkali metal formates.
Claim 25
Dependent Claim
25 words
A blend as claimed in claim 22 wherein the trimerization catalyst is present in an amount of 0.02 to 0.4 by weight of the blend.
Claim 26
Dependent Claim
45 words
A blend as claimed in claim 22 wherein the monomer is selected from the group consisting of styrene, vinyltoluene, divinyl benzene, the methyl, ethyl, n-butyl, 2-ethyl hexyl or pentaerythritol esters of acrylic and methacrylic acid, triallyl isocyanurate, vinyl acetate, diallyl fumarate, vinyl ether and acrylonitrile.
Claim 27
Dependent Claim
157 words
A blend as claimed in claim 22 wherein the polymerizable resin is an isocyanurate of urethanes of an aromatic polyisocyanate and at least one vinylidene carbonyl oxy alkanol characterized by one of the following formulas: ##STR9## wherein R 1 is hydrogen or an alkyl group containing from 1 to 4 carbon atoms, R 2 is hydrogen, alkyl containing from 1 to 12 carbon atoms, or a chlorinated, brominated, or fluorinated alkyl group containing from 1 to 12 carbon atoms, R 3 is hydrogen, alkyl containing from 1 to 12 carbon atoms, or a chlorinated, brominated, or fluorinated alkyl group containing from 1 to 12 carbon atoms, R 4 is hydrogen, methyl or ethyl, and n is from one to four, with the proviso that R 2 and R 3 on adjacent carbon atoms are not both alkyl or chlorinated, brominated, or fluorinated alkyl, that is at least one of R 2 and R 3 must be hydrogen.
Claim 28
Dependent Claim
195 words
A blend as claimed in claim 22 wherein the polymerizable resin has the following formula B--I--A--M].sub.y A--(I--B).sub.q wherein A is a radical derived from a polyoxyalkylene bisphenol A having the following formula: ##STR10## wherein R' is C 1 -C 4 alkylene group, X is halogen or a C 1 -C 4 alkyl group, a is an integer equal to from 0 to 2, and m and n are integers each of which is equal to at least 1 and the sum of which is equal to from 2.0 to about 30.0; M is a radical derived from (A) an unsaturated, aliphatic, polycarboxylic acid or an anhydride thereof, (B) a saturated aliphatic polycarboxylic acid or an anhydride thereof, (C) an aromatic polycarboxylic acid or anhydride thereof or (D) mixtures of A, B, or C; I is a radical derived from an isocyanate having an isocyanate functionality of at least 2; B is a radical derived from a monohydroxy-terminated ester of unsubstituted or substituted acrylic or methacrylic acid wherein the substituents are halogen or C 1 -C 4 alkyl groups; y is an integer equal to from 1 to about 12, and q is zero or one.
Claim 29
Dependent Claim
18 words
A blend as claimed in claim 22 wherein the trimerization catalyst is N-benzyl-trimethyl ammonium hydroxide or potassium acetate.
Claim 30
Dependent Claim
15 words
A blend as claimed in claim 22 which additionally comprises a free radical polymerization catalyst.
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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) | 1984-10-19 | 1985-04-20 | 1985-10-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-10-19 | 1989-04-20 | 1989-10-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-10-19 | 1993-04-20 | 1993-10-20 | $7700.00 | Window Closed / Lapsed |