Patent US4009307A successfully refreshed from Google Patents.
US4009307A
Expired / Lapsed
US
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Polyurea-urethane coatings
Assignee: PPG Industries Inc
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Filing: 1975-07-24
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Granted: 1977-02-22
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Expires: 1995-07-24
Abstract
Abstract Coating compositions which form polyurea-urethane coatings having excellent chemical and physical properties are prepared by blending (a) from about 2 percent to about 80 percent by weight of resin solids of an isocyanate-terminated polyurethane prepolymer consisting essentially of the reaction product of an organic diisocyanate and an organic diol, wherein said prepolymer is prepared at an NCO/OH ratio of from 2:1 to about 4:3, (b) from about 2 percent to about 60 percent by weight resin solids of an isocyanate-terminated polyurethane prepolymer consisting essentially of the reaction product of 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethylcyclohexane and a mixture of aliphatic polyols wherein at least about 30 mole percent of the total hydroxyl groups supplied by said mixture of polyols is supplied by an aliphatic polyol having at least three hydroxyl groups and wherein said prepolymer is prepared at an NCO/OH ratio of at least 1.2:1; and (c) from about 20 percent to about 50 percent by weight of resin solids of a polyketimine material consisting essentially of the reaction product of a diketimine compound having the general formula: ##STR1## wherein R is an alkylene group of 2 to 6 carbon atoms and R 1 and R 2 are hydrogen or organic radicals having from 1 to 8 carbon atoms, and a polyisocyanate material selected from the group consisting of an isocyanate-terminated polyurethane prepolymer formed by reacting an organic diisocyanate and an organic diol at an NCO/OH ratio of from about 2:1 to about 4:3 or mixtures of isocyanate-terminated prepolymers and unreacted diisocyanate formed by reacting an organic diisocyanate and an organic diol at an NCO/OH ratio of from about 3:1 to about 5:1, wherein a sufficient amount of said diketimine is reacted with said polyisocyanate compound to produce a polyketimine compound containing essentially no free NCO groups. The polyurea-urethane coatings formed from the compositions of the invention have excellent chemical and physical properties and are particularly useful as coatings for wood.
Inventors
- 👤 J. Alden Erikson
- 👤 Ken W. Niederst
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 08:49
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/10; C08G18/70; C08G18/72; C08G18/74; C08G18/75; C08G18/751; C08G18/752; C08G18/753; C08G18/755; C08G18/80; C08G18/8003; C08G18/8006; C08G18/8009
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
286 words
A coating composition comprising: A. from about 2 percent to about 80 percent by weight of resin solids of an isocyanate-terminated polyurethane prepolymer consisting essentially of the reaction product of an organic diisocyanate and an organic diol, wherein said prepolymer is prepared at an NCO/OH ratio of from about 2:1 to about 4:3; B. from about 2 percent to about 60 percent by weight of resin solids of an isocyanate-terminated polyurethane prepolymer consisting essentially of the reaction product of 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethylcyclohexane and a mixture of aliphatic polyols, wherein said prepolymer is prepared at an NCO/OH ratio of at least 1.2:1 and wherein at least about 30 mole percent of the total hydroxyl groups supplied by said mixture of polyols is supplied by an aliphatic polyol having at least three hydroxyl groups; and C. from about 20 percent to about 50 percent by weight of resin solids of a polyketimine material consisting essentially of the reaction product of a diketimine compound having the general formula: ##STR7## wherein R is an alkylene group of 2 to 6 carbon atoms and R 1 and R 2 are hydrogen or organic radicals having from 1 to 8 carbon atoms, and a polyisocyanate material selected from the group consisting of an isocyanate-terminated prepolymer formed by reacting an organic diisocyanate and an organic diols at an NCO/OH ratio of from about 2:1 to about 4:3 or a mixture of an isocyanate-terminated prepolymer and unreacted organic diisocyanate formed by reacting an organic diisocyanate and an organic diol at an NCO/OH ratio of from about 3:1 to about 5:1, and wherein a sufficient amount of said diketimine is reacted with said prepolymer or said mixture to produce a polyketimine material containing no free NCO groups.
Claim 2
Dependent Claim
286 words
A coating composition comprising: A. from about 2 percent to about 80 percent by weight of resin solids of an isocyanate-terminated polyurethane prepolymer consisting essentially of the reaction product of an organic diisocyanate and an organic diol, wherein said prepolymer is prepared at an NCO/OH ratio of from about 2:1 to about 4:3; B. from about 2 percent to about 60 percent by weight of resin solids of an isocyanate-terminated polyurethane prepolymer consisting essentially of the reaction product of 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethylcyclohexane and a mixture of aliphatic polyols, wherein said prepolymer is prepared at an NCO/OH ratio of at least 1.2:1 and wherein at least about 30 mole percent of the total hydroxyl groups supplied by said mixture of polyols is supplied by an aliphatic polyol having at least three hydroxyl groups; and C. from about 20 percent to about 50 percent by weight of resin solids of a polyketimine material consisting essentially of the reaction product of a diketimine compound having the general formula: ##STR7## wherein R is an alkylene group of 2 to 6 carbon atoms and R 1 and R 2 are hydrogen or organic radicals having from 1 to 8 carbon atoms, and a polyisocyanate material selected from the group consisting of an isocyanate-terminated prepolymer formed by reacting an organic diisocyanate and an organic diols at an NCO/OH ratio of from about 2:1 to about 4:3 or a mixture of an isocyanate-terminated prepolymer and unreacted organic diisocyanate formed by reacting an organic diisocyanate and an organic diol at an NCO/OH ratio of from about 3:1 to about 5:1, and wherein a sufficient amount of said diketimine is reacted with said prepolymer or said mixture to produce a polyketimine material containing no free NCO groups.
Claim 3
Dependent Claim
32 words
The coating composition of claim 1 wherein the organic diisocyanate of prepolymer (A) is selected from the group consisting of hydrocarbon diisocyanates, substituted hydrocarbon diisocyanates, aromatic diisocyanates, aliphatic diisocyanates, and cycloaliphatic diisocyanates.
Claim 4
Dependent Claim
19 words
The coating composition of claim 1 wherein the organic diisocyanate of prepolymer (A) is isophorone diisocyanate or 2,4-toluene diisocyanate.
Claim 5
Dependent Claim
27 words
The coating composition of claim 1 wherein the organic diol of prepolymer (A) is selected from the group consisting of polyester diols, polyether diols or mixtures thereof.
Claim 6
Dependent Claim
33 words
The coating composition of claim 1 wherein the organic diol of prepolymer (A) is a polyester diol of diethylene glycol and epsilon-caprolactone havng a rate of 3.7 lactone units per molecule of glycol.
Claim 7
Dependent Claim
19 words
The coating composition of claim 1 wherein said prepolymer of (A) is prepared at an NCO/OH ratio of 3:2.
Claim 8
Dependent Claim
27 words
The coating composition of claim 1 wherein the mixture of aliphatic polyols of prepolymer (B) may be a mixture of diols, triols, ester polyols or ether polyols.
Claim 9
Dependent Claim
21 words
The coating composition of claim 1 wherein the prepolymer of (B) is the reaction product of 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethylcyclohexane, trimethylolpropane and neopentyl glycol.
Claim 10
Dependent Claim
21 words
The coating composition of claim 1 wherein the prepolymer of (B) contains from 3 to 25 percent of free isocyanate groups.
Claim 11
Dependent Claim
17 words
The coating composition of claim 1 wherein the diketimine of (C) is diethylenetriamine methyl isobutyl ketone diketimine.
Claim 12
Dependent Claim
15 words
The coating composition of claim 1 wherein the diketimine of (C) is diisobutyl ketone diketimine.
Claim 13
Dependent Claim
29 words
The coating composition of claim 1 wherein the polyisocyanate material employed in forming the polyketimine material of (C) is an isocyanate-terminated prepolymer prepared at an NCO/OH ratio of 3:2.
Claim 14
Dependent Claim
41 words
The coating composition of claim 12 wherein said prepolymer consists essentially of the reaction product of isophorone diisocyanate or 2,4-toluene diisocyanate and a polyester diol of diethylene glycol and epsilon-caprolactone having a ratio of 3.7 lactone units per molecule of glycol.
Claim 15
Dependent Claim
68 words
The coating composition of claim 1 wherein the polyisocyanate material employed in forming the polyketimine material of (C) is a mixture of an isocyanate-terminated prepolymer and unreacted organic diisocyanate formed by reacting isophorone diisocyanate or 2,4-toluene diisocyanate and a polyester diol of diethylene glycol and epsilon-caprolactone having a ratio of 3.7 lactone units per molecular of glycol at an NCO/OH ratio of from about 3:1 to about 5:1.
Claim 16
Dependent Claim
17 words
The coating composition of claim 14 wherein said mixture is prepared at an NCO/OH ratio of 3:1.
Claim 17
Independent Claim
338 words
A method of preparing a polyurea-urethane coating comprising the steps of: A. preparing an isocyanate-terminated polyurethane prepolymer consisting essentially of the reaction product of an organic diisocyanate and an organic diol, said prepolymer being prepared at an NCO/OH ratio of from about 2:1 to about 4:3; B. preparing an isocyanate-terminated prepolymer consisting essentially of the reaction of 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethylcyclohexane and a mixture of aliphatic polyols, wherein said prepolymer is prepared at an NCO/OH ratio of at least 1.2:1, and wherein at least about 30 mole percent of the total hydroxyl groups supplied by said mixture of polyols is supplied by an aliphatic polyol having at least three hydroxyl groups; C. preparing a polyketimine material consisting essentially of the reaction product of a diketimine compound having the general formula: r1 ? ##STR8## wherein R is an alkylene group of 2 to 6 carbon atoms and R 1 and R 2 are hydrogen or organic radicals having from 1 to 8 carbon atoms, an a polyisocyanate material selected from the group consisting of an isocyanate-terminated prepolymer formed by reacting an organic diisocyanate and an organic diol at an NCO/OH ratio of from about 2:1 to about 4:3 or a mixture of an isocyanate-terminated prepolymer and unreacted organic diisocyanate formed by reacting an organic diisocyanate and an organic diol at an NCO/OH ratio of from about 3:1 to about 5:1, and wherein a sufficient amount of said diketimine is reacted with said prepolymer or said mixture to produce a polyketimine material containing no free NCO groups; D. blending from about 2 percent to about 80 percent by weight of resin solids of the prepolymer of step (A), from about 2 percent to about 60 percent by weight of resin solids of the prepolymer of step (B), and from about 20 percent to about 50 percent by weight of the polyketimine material of step (C) to form a coating composition; E. applying said coating composition to a substrate; and F. curing said applied coating composition to provide a polyureaurethane coating on said substrate.
Claim 18
Independent Claim
338 words
A method of preparing a polyurea-urethane coating comprising the steps of: A. preparing an isocyanate-terminated polyurethane prepolymer consisting essentially of the reaction product of an organic diisocyanate and an organic diol, said prepolymer being prepared at an NCO/OH ratio of from about 2:1 to about 4:3; B. preparing an isocyanate-terminated prepolymer consisting essentially of the reaction of 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethylcyclohexane and a mixture of aliphatic polyols, wherein said prepolymer is prepared at an NCO/OH ratio of at least 1.2:1, and wherein at least about 30 mole percent of the total hydroxyl groups supplied by said mixture of polyols is supplied by an aliphatic polyol having at least three hydroxyl groups; C. preparing a polyketimine material consisting essentially of the reaction product of a diketimine compound having the general formula: r1 ? ##STR8## wherein R is an alkylene group of 2 to 6 carbon atoms and R 1 and R 2 are hydrogen or organic radicals having from 1 to 8 carbon atoms, an a polyisocyanate material selected from the group consisting of an isocyanate-terminated prepolymer formed by reacting an organic diisocyanate and an organic diol at an NCO/OH ratio of from about 2:1 to about 4:3 or a mixture of an isocyanate-terminated prepolymer and unreacted organic diisocyanate formed by reacting an organic diisocyanate and an organic diol at an NCO/OH ratio of from about 3:1 to about 5:1, and wherein a sufficient amount of said diketimine is reacted with said prepolymer or said mixture to produce a polyketimine material containing no free NCO groups; D. blending from about 2 percent to about 80 percent by weight of resin solids of the prepolymer of step (A), from about 2 percent to about 60 percent by weight of resin solids of the prepolymer of step (B), and from about 20 percent to about 50 percent by weight of the polyketimine material of step (C) to form a coating composition; E. applying said coating composition to a substrate; and F. curing said applied coating composition to provide a polyureaurethane coating on said substrate.
Claim 19
Dependent Claim
23 words
The method of claim 16 wherein the organic diisocyanate employed in forming the prepolymer in step (A) is isophorone diisocyanate or 2,4-toluene diisocyanate.
Claim 20
Dependent Claim
37 words
The method of claim 16 wherein the organic diol employed in forming the prepolymer of step (A) is a polyester diol of diethylene glycol and epsilon-caprolactone having a ratio of 3.7 lactone units per molecule of glycol.
Claim 21
Dependent Claim
19 words
The method of claim 16 wherein the prepolymer of step (A) is prepared at an NCO/OH ratio of 3:2.
Claim 22
Dependent Claim
30 words
The method of claim 16 wherein the mixture of aliphatic polyols employed in preparing the prepolymer of step (B) is a mixture of diols, triols, ester polyols or ether polyols.
Claim 23
Dependent Claim
21 words
The method of claim 16 wherein the prepolymer of step (B) is prepared by reacting 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethylcyclohexane, trimethylol propane and neopentyl glycol.
Claim 24
Dependent Claim
23 words
The method of claim 16 wherein the diketimine employed in preparing the polyketamine material of step (C) is diethylenetriamine methyl isobutyl ketone diketimine.
Claim 25
Dependent Claim
21 words
The method of claim 16 wherein the diketimine employed in preparing the polyketamine material of step (C) is diisobutyl ketone diketamine.
Claim 26
Dependent Claim
29 words
The method of claim 16 wherein the polyisocyanate material employed in preparing the polyketamine material of step (C) is an isocyanate-terminated prepolymer prepared at an NCO/OH ratio of 4:3.
Claim 27
Dependent Claim
40 words
The method of claim 24 wherein said prepolymer consists essentially of the reaction product of isophorone diisocyanate or 2,4-toluene diisocyanate and a polyester diol of diethylene glycol and epsilon-caprolactone having a ratio of 3.7 lactone units per molecule of glycol.
Claim 28
Dependent Claim
68 words
The method of claim 16 wherein the polyisocyanate material employed in preparing the polyketimine material of step (C) is a mixture of an isocyanate-terminated prepolymer and unreacted organic diisocyanate formed by reacting isophorone diisocyanate or 2,4-toluene diisocyanate and a polyester diol of ethylene glycol and epsilon-caprolactone having a ratio of 3.7 lactone units per molecule of glycol at an NCO/OH ratio of from about 3:1 to about 5:1.
Claim 29
Dependent Claim
14 words
The method of claim 16 wherein the curing of step (F) is moisture curing.
Claim 30
Dependent Claim
16 words
The method of claim 16 wherein the curing of step (F) is moisture and heat curing.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-02-22 | 1980-08-23 | 1981-02-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-02-22 | 1984-08-23 | 1985-02-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-02-22 | 1988-08-23 | 1989-02-22 | $7700.00 | Window Closed / Lapsed |