Patent US3989676A successfully refreshed from Google Patents.
US3989676A
Expired / Lapsed
US
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Polyurethane coating formulations based on polyepoxide-caprolactone polyols and polyisocyanates
Assignee: Union Carbide Corp
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Filing: 1975-05-05
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Granted: 1976-11-02
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Expires: 1995-05-05
Abstract
Abstract Compositions useful for the formation of high performance coatings are provided as the reaction products of a caprolactone polyol having an average hydroxyl functionality of at least three and a polyepoxide. The products formed by reaction of a caprolactone triol and a cycloaliphatic diepoxide are used with particular advantage as the active hydrogen-containing component of polyurethane formulations to be applied as coatings on external surfaces of aircraft.
Inventors
- 👤 Richard Michael Gerkin
- 👤 Lowell Ray Comstock
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 13:36
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/42; C08G18/4266; C08G18/4269; C08G18/4277; C08G18/4244; C09; C09D; C09D163/00
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
81 words
A two-package urethane coating formulation which comprises (1) an organic polyisocyanate, and (2) a polyol composition prepared by the reaction of (a) and (b) where (a) is a caprolactone polyol having an average of at least three hydroxyl groups per molecule and (b) is a polyepoxide having at least two vicinal epoxy groups per molecule, the amount of reactant (a) employed in forming said polyol composition being at least sufficient to effect substantially complete reaction of the epoxy groups of (b).
Claim 2
Dependent Claim
81 words
A two-package urethane coating formulation which comprises (1) an organic polyisocyanate, and (2) a polyol composition prepared by the reaction of (a) and (b) where (a) is a caprolactone polyol having an average of at least three hydroxyl groups per molecule and (b) is a polyepoxide having at least two vicinal epoxy groups per molecule, the amount of reactant (a) employed in forming said polyol composition being at least sufficient to effect substantially complete reaction of the epoxy groups of (b).
Claim 3
Dependent Claim
122 words
A two-package urethane coating formulation which comprises (1) an organic polyisocyanate, and (2) a polyol composition formed by reaction at a temperature from about 100° to about 190° C. of (a) and (b) where: a. is a caprolactone polyol having an average of from three to six hydroxyl groups per molecule; and b. is a cycloaliphatic diepoxide having the formula, ##SPC11## where R represents hydrogen or an alkyl group having from one to four carbon atoms, R° represents a valence bond or a bivalent hydrocarbon radical having from 1 to 9 carbon atoms, and a has a value of zero or one; the mole ratio of (a) to (b) employed in forming said polyol composition being from about 1.8:1 to about 2.5:1.
Claim 4
Dependent Claim
122 words
A two-package urethane coating formulation which comprises (1) an organic polyisocyanate, and (2) a polyol composition formed by reaction at a temperature from about 100° to about 190° C. of (a) and (b) where: a. is a caprolactone polyol having an average of from three to six hydroxyl groups per molecule; and b. is a cycloaliphatic diepoxide having the formula, ##SPC11## where R represents hydrogen or an alkyl group having from one to four carbon atoms, R° represents a valence bond or a bivalent hydrocarbon radical having from 1 to 9 carbon atoms, and a has a value of zero or one; the mole ratio of (a) to (b) employed in forming said polyol composition being from about 1.8:1 to about 2.5:1.
Claim 5
Dependent Claim
92 words
A two-package urethane coating formulation which comprises (1) an organic polyisocyanate, and (2) a polyol composition prepared by the reaction of (a) and (b) where: (a) is a caprolactone triol having an average hydroxyl number from about 185 to about 560 prepared by the reaction of trimethylolpropane and epsilon-caprolactone, and (b) is 3,4-epoxycyclohexylmethyl (3,4-epoxycyclohexane)carboxylate, the said reaction of (a) and (b) being effected at a temperature between about 100° and about 190° C. in the presence of a tin carboxylate as catalyst, employing about two moles of (a) per mole of (b).
Claim 6
Dependent Claim
92 words
A two-package urethane coating formulation which comprises (1) an organic polyisocyanate, and (2) a polyol composition prepared by the reaction of (a) and (b) where: (a) is a caprolactone triol having an average hydroxyl number from about 185 to about 560 prepared by the reaction of trimethylolpropane and epsilon-caprolactone, and (b) is 3,4-epoxycyclohexylmethyl (3,4-epoxycyclohexane)carboxylate, the said reaction of (a) and (b) being effected at a temperature between about 100° and about 190° C. in the presence of a tin carboxylate as catalyst, employing about two moles of (a) per mole of (b).
Claim 7
Dependent Claim
83 words
A polyurethane coating composition comprising the reaction product of (1) an organic polyisocyanate and (2) a polyol composition prepared by the reaction of (a) and (b) where (a) is a caprolactone polyol having an average of at least three hydroxyl groups per molecule and (b) is a polyepoxide having at least two vicinal epoxy groups per molecule, the amount of reactant (a) employed in forming said polyol composition being at least sufficient to effect substantially complete reaction of the epoxy groups of (b).
Claim 8
Dependent Claim
83 words
A polyurethane coating composition comprising the reaction product of (1) an organic polyisocyanate and (2) a polyol composition prepared by the reaction of (a) and (b) where (a) is a caprolactone polyol having an average of at least three hydroxyl groups per molecule and (b) is a polyepoxide having at least two vicinal epoxy groups per molecule, the amount of reactant (a) employed in forming said polyol composition being at least sufficient to effect substantially complete reaction of the epoxy groups of (b).
Claim 9
Dependent Claim
124 words
A polyurethane coating composition comprising the reaction product of (1) an organic polyisocyanate and (2) a polyol composition formed by reaction at a temperature from about 100° to about 190° C. of (a) and (b) where: a. is a caprolactone polyol having an average of from three to six hydroxyl groups per molecule; and b. is a cycloaliphatic diepoxide having the formula, ##SPC12## where R represents hydrogen or an alkyl group having from one to four carbon atoms, R° represents a valence bond or a bivalent hydrocarbon radical having from 1 to 9 carbon atoms, and a has a value of zero or one; the mole ratio of (a) to (b) employed in forming said polyol composition being from about 1.8:1 to about 2.5:1.
Claim 10
Dependent Claim
124 words
A polyurethane coating composition comprising the reaction product of (1) an organic polyisocyanate and (2) a polyol composition formed by reaction at a temperature from about 100° to about 190° C. of (a) and (b) where: a. is a caprolactone polyol having an average of from three to six hydroxyl groups per molecule; and b. is a cycloaliphatic diepoxide having the formula, ##SPC12## where R represents hydrogen or an alkyl group having from one to four carbon atoms, R° represents a valence bond or a bivalent hydrocarbon radical having from 1 to 9 carbon atoms, and a has a value of zero or one; the mole ratio of (a) to (b) employed in forming said polyol composition being from about 1.8:1 to about 2.5:1.
Claim 11
Dependent Claim
95 words
A polyurethane coating composition comprising the reaction product of (1) an organic polyisocyanate and (2) the polyol composition prepared by the reaction of (a) and (b) where (a) is a caprolactone triol having an average hydroxyl number from about 185 to about 560 prepared by the reaction of trimethylolpropane and epsilon-caprolactone, and (b) is 3,4-epoxycyclohexylmethyl (3,4-epoxycyclohexane) carboxylate, the said reaction of (a) and (b) being effected at a temperature between about 100° and about 190° C. in the presence of a tin carboxylate as catalyst, employing about two moles of (a) per mole of (b).
Claim 12
Dependent Claim
95 words
A polyurethane coating composition comprising the reaction product of (1) an organic polyisocyanate and (2) the polyol composition prepared by the reaction of (a) and (b) where (a) is a caprolactone triol having an average hydroxyl number from about 185 to about 560 prepared by the reaction of trimethylolpropane and epsilon-caprolactone, and (b) is 3,4-epoxycyclohexylmethyl (3,4-epoxycyclohexane) carboxylate, the said reaction of (a) and (b) being effected at a temperature between about 100° and about 190° C. in the presence of a tin carboxylate as catalyst, employing about two moles of (a) per mole of (b).
Claim 13
Dependent Claim
127 words
A polyurethane coating composition comprising the reaction product of: 1. a biuret-containing aliphatic polyisocyanate; and 2. a polyol composition prepared by the reaction of (a) and (b) where (a) is a caprolactone triol having an average hydroxyl number from about 185 to about 560 prepared by the reaction of trimethylolpropane and epsilon-caprolactone and (b) is 3,4-epoxycyclohexylmethyl (3,4-epoxycyclohexane) carboxylate, the said reaction of (a) and (b) being effected at a temperature between about 100° and about 190° C. in the presence of a tin carboxylate as catalyst, employing about two moles of (a) per mole of (b); the amount of said reactants (1) and (2) employed in forming said coating composition being sufficient to provide an --NCO to --OH equivalent ratio of from about 1:1 to about 1.4:1.
Claim 14
Dependent Claim
127 words
A polyurethane coating composition comprising the reaction product of: 1. a biuret-containing aliphatic polyisocyanate; and 2. a polyol composition prepared by the reaction of (a) and (b) where (a) is a caprolactone triol having an average hydroxyl number from about 185 to about 560 prepared by the reaction of trimethylolpropane and epsilon-caprolactone and (b) is 3,4-epoxycyclohexylmethyl (3,4-epoxycyclohexane) carboxylate, the said reaction of (a) and (b) being effected at a temperature between about 100° and about 190° C. in the presence of a tin carboxylate as catalyst, employing about two moles of (a) per mole of (b); the amount of said reactants (1) and (2) employed in forming said coating composition being sufficient to provide an --NCO to --OH equivalent ratio of from about 1:1 to about 1.4:1.
References Cited (Backward Citations)
US3169945A
Cited
US3408421A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-11-02 | 1980-05-03 | 1980-11-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-11-02 | 1984-05-03 | 1984-11-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-11-02 | 1988-05-03 | 1988-11-02 | $7700.00 | Window Closed / Lapsed |