US4182830A
Expired / Lapsed
US
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Vinyl ester urethanes
Assignee: Beazer East Inc
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Filing: 1978-07-24
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Granted: 1980-01-08
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Expires: 1998-07-24
Abstract
Abstract Vinyl ester urethane resins prepared by reacting (a) the reaction product of a polyoxyalkylene bisphenol A and a polycarboxylic acid or anhydride, (b) a polyfunctional isocyanate having an average isocyanate functionality of greater than two, and (c) a monohydroxyl-terminated ester of acrylic acid or methacrylic acid are useful in thermosetting fiber reinforced laminates.
Inventors
- 👤 Ernest C. Ford, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 17:58
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/28; C08G18/40; C08G18/42; C08G18/4244; C08G18/4247; C08G18/4255; C08G18/67; C08G18/671; C08G18/672; C08G18/673; C08G18/68; C08G18/683; Y; Y10; Y10S; Y10S525/00; Y10S525/92
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
178 words
A vinyl ester urethane resin having 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: ##STR9## 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 from about 2.0 to about 8.0; 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 average isocyanate functionality greater than two, B is a radical derived from a monohydroxyl-terminated ester of acrylic acid or a methacrylic acid, y is an integer equal to from 1 to about 12. q is an integer of one or zero.
Claim 2
Dependent Claim
178 words
A vinyl ester urethane resin having 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: ##STR9## 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 from about 2.0 to about 8.0; 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 average isocyanate functionality greater than two, B is a radical derived from a monohydroxyl-terminated ester of acrylic acid or a methacrylic acid, y is an integer equal to from 1 to about 12. q is an integer of one or zero.
Claim 3
Dependent Claim
23 words
A vinyl ester urethane as claimed in claim 1 wherein X is halogen and a is an integer equal to 1 or 2.
Claim 4
Dependent Claim
23 words
A vinyl ester urethane resin as claimed in claim 2 wherein X is selected from the group consisting of bromine, chlorine, and fluorine.
Claim 5
Dependent Claim
26 words
A vinyl ester urethane resin as claimed in claim 1 wherein the sum of m and n is equal to from about 2.0 to about 6.0.
Claim 6
Dependent Claim
31 words
A vinyl ester urethane resin as claimed in claim 1 wherein the polycarboxylic acid or anhydride thereof is selected from the group consisting of fumaric acid, maleic acid, and maleic anhydride.
Claim 7
Dependent Claim
19 words
A vinyl ester urethane resin as claimed in claim 1 wherein y is equal to about 1 to 5.
Claim 8
Dependent Claim
34 words
A vinyl ester urethane resin as claimed in claim 1 wherein the polyfunctional isocyanate is selected from the group consisting of polymethylene polyphenylene polyfunctional isocyanate having an average isocyanate functionality of more than two.
Claim 9
Dependent Claim
25 words
A vinyl ester urethane resin as claimed in claim 7 wherein the polyfunctional isocyanate has a average isocyanate functionality of from between 2.2 to 4.0.
Claim 10
Dependent Claim
55 words
A vinyl ester urethane resin as claimed in claim 1 wherein the hydroxyl-terminated ester of acrylic acid has the following formula: ##STR10## wherein R is hydrogen or C 1 -C 4 alkyl, R' is an alkylene group containing 2 to 5 carbon atoms, and n is an integer equal to from 1 to about 3.
Claim 11
Dependent Claim
20 words
A vinyl ester urethane resin as claimed in claim 9 wherein n is equal to from 1 to about 2.
Claim 12
Dependent Claim
28 words
A vinyl ester urethane resin as claimed in claim 1 wherein the hydroxyl-terminated ester is hydroxypropyl methacrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, and hydroxy ethyl acrylate or mixtures thereof.
Claim 13
Independent Claim
182 words
A method of preparing a vinyl ester urethane resin, said method comprising; (a) preparing a bisphenol A hydroxy terminated polyester oligomer by reacting a polyoxyalkylene bisphenol A having the following formula: ##STR11## 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 about 2.0 to about 8.0; with an (A) unsaturated aliphatic polycarboxylic acid or an anhydride thereof, (B) saturated aliphatic polycarboxylic acid or an anhydride thereof, (C) an aromatic polycarboxylic acid or anhydride thereof or (D) a mixture of A, B, or C in a mole ratio of polyoxy alkylene bisphenol A to polycarboxylic acid or anhydride equal to from about 2:1 to about 13:12 and (b) combining the bisphenol A hydroxy terminated polyester oligomer with a polyfunctional isocyanate having an average isocyanate functionality of greater than two and a monohydroxyl-terminated ester of acrylic or methacrylic acid.
Claim 14
Independent Claim
182 words
A method of preparing a vinyl ester urethane resin, said method comprising; (a) preparing a bisphenol A hydroxy terminated polyester oligomer by reacting a polyoxyalkylene bisphenol A having the following formula: ##STR11## 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 about 2.0 to about 8.0; with an (A) unsaturated aliphatic polycarboxylic acid or an anhydride thereof, (B) saturated aliphatic polycarboxylic acid or an anhydride thereof, (C) an aromatic polycarboxylic acid or anhydride thereof or (D) a mixture of A, B, or C in a mole ratio of polyoxy alkylene bisphenol A to polycarboxylic acid or anhydride equal to from about 2:1 to about 13:12 and (b) combining the bisphenol A hydroxy terminated polyester oligomer with a polyfunctional isocyanate having an average isocyanate functionality of greater than two and a monohydroxyl-terminated ester of acrylic or methacrylic acid.
Claim 15
Dependent Claim
23 words
A method as claimed in claim 12 wherein R' is C 1 -C 4 alkylene group containing from 2 to 3 carbon atoms.
Claim 16
Dependent Claim
20 words
A method as claimed in claim 12 wherein X is selected from the group consisting of bromine, chlorine, and fluorine.
Claim 17
Dependent Claim
23 words
A method as claimed in claim 12 wherein the sum of m and n is equal to from about 2.0 to about 6.0.
Claim 18
Dependent Claim
28 words
A method as claimed in claim 12 wherein the polycarboxylic acid or anhydride thereof is selected from the group consisting of fumaric acid, maleic acid, and maleic anhydride.
Claim 19
Dependent Claim
17 words
A method as claimed in claim 16 wherein the polycarboxylic acid or anhydride thereof is maleic anhydride.
Claim 20
Dependent Claim
28 words
A method as claimed in claim 12 wherein the molar ratio of polyoxyalkylene bisphenol A to acid or anhydride is equal to from about 2:1 to about 13:12.
Claim 21
Dependent Claim
30 words
A method as claimed in claim 12 wherein the polyfunctional isocyanate is selected from the group consisting polymethylene polyphenylene polyfunctional isocyanates having an average isocyanate functionality of more than two.
Claim 22
Dependent Claim
21 words
A method as claimed in claim 19 wherein the polyfunctional isocyanate has an average isocyanate functionality of from 2.2 to 4.0.
Claim 23
Dependent Claim
30 words
A method as claimed in claim 12 wherein the mol amount of polyfunctional isocyanate is equal to at least 1 mol per mol of bisphenol A hydroxy terminated polyester oligomer.
Claim 24
Dependent Claim
52 words
A method as claimed in claim 12 wherein the hydroxyl-terminated ester of acrylic has the following formula: ##STR12## wherein R is a C 1 -C 4 alkyl, or hydrogen R' is an alkylene group containing 2 to 5 carbon atoms, and n is an integer equal to from 1 to about 3.
Claim 25
Dependent Claim
17 words
A method as claimed in claim 22 wherein n is equal to from 1 to about 2.
Claim 26
Dependent Claim
26 words
A method as claimed in claim 12 wherein the monohydroxyl-terminated ester is hydroxypropyl methacrylate, hydroxy ethyl methacrylate, hydroxypropyl acrylate, and hydroxy ethyl acrylate or mixtures thereof.
Claim 27
Dependent Claim
33 words
A method as claimed in claim 12 wherein the bisphenol A hydroxy-terminated polyester oligomer is reacted with the polyfunctional isocyanate and the hydroxyl-terminated ester of acrylic acid in the presence of a solvent.
Claim 28
Dependent Claim
33 words
A method as claimed in claim 12 wherein the hydroxyl-terminated ester of acrylic acid is blended with the bisphenol A hydroxyl-terminated polyester oligomer and the blend is then reacted with the polyfunctional isocyanate.
Claim 29
Dependent Claim
183 words
A laminate composition comprising (a) a vinyl ester urethane resin having 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: ##STR13## wherein R' is a C 1 -C 4 alkylene group, X is halogen or a C 1 -C 4 alkylene group, a is an integer equal to from 0 to 2, and m and n are integers each of which is equal to at at least 1 and the sum of which is equal to from about 2.0 to about 8.0; M is the residue of (A) an unsaturated aliphatic polycarboxylic acid or 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 the residue of a polyfunctional isocyanate having an isocyanate functionality of greater than two, B is the residue of a monohydroxyl-terminated ester of acrylic or methacrylic acid: y is an integer equal to from 1 to about 12 and q is one or zero; (B) a chemical initiator.
Claim 30
Dependent Claim
183 words
A laminate composition comprising (a) a vinyl ester urethane resin having 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: ##STR13## wherein R' is a C 1 -C 4 alkylene group, X is halogen or a C 1 -C 4 alkylene group, a is an integer equal to from 0 to 2, and m and n are integers each of which is equal to at at least 1 and the sum of which is equal to from about 2.0 to about 8.0; M is the residue of (A) an unsaturated aliphatic polycarboxylic acid or 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 the residue of a polyfunctional isocyanate having an isocyanate functionality of greater than two, B is the residue of a monohydroxyl-terminated ester of acrylic or methacrylic acid: y is an integer equal to from 1 to about 12 and q is one or zero; (B) a chemical initiator.
References Cited (Backward Citations)
US3754909A
Cited
US3876726A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-01-07 | 1983-07-09 | 1984-01-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-01-07 | 1987-07-09 | 1988-01-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-01-07 | 1991-07-09 | 1992-01-08 | $7700.00 | Window Closed / Lapsed |