US4376834A
Expired / Lapsed
US
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Polyurethane prepared by reaction of an organic polyisocyanate, a chain extender and an isocyanate-reactive material of m.w. 500-20,000 characterized by the use of only 2-25 percent by weight of the latter material
Assignee: Dow Chemical Co
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Filing: 1981-10-14
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Granted: 1983-03-15
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Expires: 2001-10-14
Abstract
Abstract Polyurethane resins are described having high impact strength and other structural strength properties, and significantly improved resistance to deformation by heat. The properties of these materials are such as to make them comparable to engineering thermoplastics such as nylon and like materials commonly used to fabricate structural components such as automotive parts, equipment housing, sporting goods, furniture, toys, household and like consumer goods. The resins are prepared from organic polyisocyanates, an isocyanate-reactive material (polyol, polyamine, etc.) having an average functionality of at least 1.9, a Tg less than 20° C. and molecular weight of 500-20,000, and one or more low molecular weight extenders the major distinguishing feature being the markedly lower proportion by weight (2 to 25 percent) in which the isocyanate-reactive material is employed as compared with polyurethane resins conventionally prepared in the art. Depending upon the particular combination of reactants employed the polyurethanes of the invention can be thermoplastic or thermoset and can be prepared in both cellular and non-cellular form.
Inventors
- 👤 David J. Goldwasser
- 👤 Kemal Onder
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 15:34
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/74; C08G18/76; C08G18/7657; C08G18/7664; C08G18/08; C08G18/10; C08G18/28; C08G18/65; C08G18/6505; C08G2120/00
Claims Analysis
Total Claims: 40
Claim 1
Independent Claim
148 words
A polyurethane characterized by high impact resistance, high flexural modulus, and a heat deflection temperature of at least 50° C. at 264 psi which comprises the product of reaction of (a) an organic polyisocyanate; (b) an isocyanate-reactive material having an average functionality of at least 1.9, a glass transition temperature (Tg) of less than 20° C., and a molecular weight in the range of about 500 to about 20,000; and (c) at least one chain extender having a functionality from 2 to 3 and a molecular weight from about 50 to about 400; said polyurethane being further characterized in that the proportion by weight of said isocyanate-reactive material (b) in said polyurethane is from about 2 to about 25 percent and the overall ratio of isocyanate groups to active hydrogen groups in said reactants employed to prepare said polyurethane is in the range of 0.95:1 to about 1.05:1.
Claim 2
Dependent Claim
148 words
A polyurethane characterized by high impact resistance, high flexural modulus, and a heat deflection temperature of at least 50° C. at 264 psi which comprises the product of reaction of (a) an organic polyisocyanate; (b) an isocyanate-reactive material having an average functionality of at least 1.9, a glass transition temperature (Tg) of less than 20° C., and a molecular weight in the range of about 500 to about 20,000; and (c) at least one chain extender having a functionality from 2 to 3 and a molecular weight from about 50 to about 400; said polyurethane being further characterized in that the proportion by weight of said isocyanate-reactive material (b) in said polyurethane is from about 2 to about 25 percent and the overall ratio of isocyanate groups to active hydrogen groups in said reactants employed to prepare said polyurethane is in the range of 0.95:1 to about 1.05:1.
Claim 3
Dependent Claim
33 words
A polyurethane according to claim 1 wherein the amount of said component (b) is within the range of about 4 to about 15 percent by weight based on the weight of said polyurethane.
Claim 4
Dependent Claim
16 words
A polyurethane according to claim 1 or 2 wherein the component (b) comprises a polyether polyol.
Claim 5
Dependent Claim
39 words
A polyurethane according to claim 3 wherein the polyether polyol comprises a polyoxypropylene polyoxyethylene triol having a primary hydroxyl content of at least about 80 percent and a molecular weight in the range of about 2000 to about 20,000.
Claim 6
Dependent Claim
14 words
A polyurethane according to claim 3 wherein the polyether polyol comprises a polytetramethylene glycol.
Claim 7
Dependent Claim
16 words
A polyurethane according to claim 1 or 2 wherein the component (b) comprises a polyester polyol.
Claim 8
Dependent Claim
23 words
A polyurethane according to claim 1 or 2 wherein the component (b) comprises a mixture of a polyether polyol and a polyester polyol.
Claim 9
Dependent Claim
13 words
A polyurethane according to claim 1 wherein the organic polyisocyanate is 4,4'-methylenebis(phenyl isocyanate).
Claim 10
Dependent Claim
33 words
A polyurethane according to claim 8 wherein said 4,4'-methylenebis(phenyl isocyanate) is employed in admixture with the corresponding 2,4'-isomer in an amount up to about 70 percent by weight based on total diisocyanate mixture.
Claim 11
Dependent Claim
37 words
A polyurethane according to claim 8 wherein said 4,4'-methylenebis(phenyl isocyanate) has been treated previously to convert a minor proportion thereof to the corresponding carbodiimide thereby to form a diisocyanate which is a stable liquid at ambient temperature.
Claim 12
Dependent Claim
37 words
A polyurethane according to claim 8 wherein said 4,4'-methylenebis(phenyl isocyanate) has been reacted previously with a minor amount of at least one aliphatic diol thereby to form a diisocyanate which is a stable liquid at ambient temperature.
Claim 13
Dependent Claim
22 words
A polyurethane according to claim 8 wherein said 4,4'-methylenebis(phenyl isocyanate) is employed in admixture with a minor amount of polymethylene polyphenyl polyisocyanate.
Claim 14
Dependent Claim
14 words
A polyurethane according to claim 1 wherein said chain extender comprises an aliphatic diol.
Claim 15
Dependent Claim
12 words
A polyurethane according to claim 13 wherein said aliphatic diol is 1,6-hexanediol.
Claim 16
Dependent Claim
12 words
A polyurethane according to claim 13 wherein said aliphatic diol is 1,4-butanediol.
Claim 17
Dependent Claim
18 words
A polyurethane according to claim 13 wherein said aliphatic diol is a mixture of 1,4-butanediol and neopentyl glycol.
Claim 18
Dependent Claim
12 words
A polyurethane according to claim 13 wherein said aliphatic diol is 1,4-cyclohexanedimethanol.
Claim 19
Dependent Claim
17 words
A polyurethane according to claim 13 wherein said aliphatic diol is a mixture of 1,4-cyclohexanedimethanol and 1,6-hexanediol.
Claim 20
Dependent Claim
71 words
A polyurethane according to claim 1 wherein said extender is the product obtained by reacting an aliphatic diol with a member selected from the class consisting of (a) caprolactone in the mole ratio of from about 0.01 to about 2 moles of caprolactone per mole of aliphatic diol and (b) adipic acid in the mole ratio of from about 0.01 to about 0.8 mole of acid per mole of aliphatic diol.
Claim 21
Dependent Claim
143 words
A thermoplastic polyurethane characterized by high impact resistance, high flexural modulus, and a heat deflection temperature of at least 50° C. at 264 psi which comprises the product of reaction of: (a) an organic diisocyanate; (b) an isocyanate-reactive material having an average functionality of at least 1.9, a glass transition temperature (Tg) of less than 20° C., and a molecular weight in the range of about 500 to about 20,000; and (c) at least one chain extender diol having a molecular weight from about 50 to about 400; said polyurethane being further characterized in that the proportion by weight of said component (b) in said polyurethane is from about 2 to about 25 percent and the overall ratio of isocyanate groups to active hydrogen groups in said reactants employed to prepare said polyurethane is in the range of about 0.95:1 to about 1.05:1.
Claim 22
Dependent Claim
143 words
A thermoplastic polyurethane characterized by high impact resistance, high flexural modulus, and a heat deflection temperature of at least 50° C. at 264 psi which comprises the product of reaction of: (a) an organic diisocyanate; (b) an isocyanate-reactive material having an average functionality of at least 1.9, a glass transition temperature (Tg) of less than 20° C., and a molecular weight in the range of about 500 to about 20,000; and (c) at least one chain extender diol having a molecular weight from about 50 to about 400; said polyurethane being further characterized in that the proportion by weight of said component (b) in said polyurethane is from about 2 to about 25 percent and the overall ratio of isocyanate groups to active hydrogen groups in said reactants employed to prepare said polyurethane is in the range of about 0.95:1 to about 1.05:1.
Claim 23
Dependent Claim
14 words
A thermoplastic polyurethane according to claim 20 wherein the organic diisocyanate comprises 4,4'-methylenebis(phenyl isocyanate).
Claim 24
Dependent Claim
23 words
A thermoplastic polyurethane according to claim 21 wherein the 4,4'-methylenebis(phenyl isocyanate) is employed in admixture with a minor amount of the corresponding 2,4'-isomer.
Claim 25
Dependent Claim
38 words
A thermoplastic polyurethane according to claim 21 wherein said 4,4'-methylenebis(phenyl isocyanate) has been previously reacted with a minor amount of at least one aliphatic diol thereby to form a diisocyanate which is a stable liquid at ambient temperature.
Claim 26
Dependent Claim
51 words
A thermoplastic polyurethane according to claim 21 wherein said 4,4'-methylenebis(phenyl isocyanate) is employed in admixture with a minor amount of a 4,4'-methylenebis(phenyl isocyanate) which has previously been treated to convert a minor proportion thereof to the corresponding carbodiimide thereby to form a product which is a stable liquid at ambient temperature.
Claim 27
Dependent Claim
89 words
A thermoplastic polyurethane according to claim 20 or 21 wherein said chain extender diol is selected from the class consisting of 1,4-butanediol, neopentyl, glycol, 1,6-hexanediol, 1,4-cyclohexanedimethanol, the product obtained by reacting 1,4-cyclohexanedimethanol with caprolactone in the mole ratio of from about 0.01 to about 2 moles of caprolactone per mole of 1,4-cyclohexanedimethanol, and the product obtained by reacting adipic acid and 1,4-cyclohexanedimethanol in the mole ratio of from about 0.01 to about 0.8 mole of acid per mole of 1,4-cyclohexanedimethanol, and mixtures of two or more of said diols.
Claim 28
Dependent Claim
17 words
A thermoplastic polyurethane according to claim 20 or 21 wherein said component (b) comprises a polyether polyol.
Claim 29
Dependent Claim
40 words
A thermoplastic polyurethane according to claim 26 wherein the polyether polyol comprises a polyoxypropylene polyoxyethylene triol having a primary hydroxyl content of at least about 80 percent and a molecular weight in the range of about 2000 to about 20,000.
Claim 30
Dependent Claim
15 words
A thermoplastic polyurethane according to claim 26 wherein the polyether polyol comprises a polytetramethylene glycol.
Claim 31
Dependent Claim
15 words
A thermoplastic polyurethane according to claim 20 wherein the component (b) comprises a polyester polyol.
Claim 32
Dependent Claim
21 words
A thermoplastic polyurethane according to claim 20 wherein the component (b) comprises a mixture of a polyether polyol and polyester polyol.
Claim 33
Dependent Claim
110 words
A thermoplastic polyurethane characterized by high impact resistance, high flexural modulus, and a heat deflection temperature of at least 50° C. at 264 psi which comprises the product of reaction of: (a) 4,4'-methylenebis(phenyl isocyanate); (b) a polyether polyol having an average functionality of at least 1.9 and a molecular weight in the range of about 500 to about 20,000; and (c) at least one aliphatic diol chain extender having a molecular weight from about 50 to about 400; said polyurethane being further characterized in that the proportion by weight of said polyether polyol in said polyurethane is from about 4 to about 15 percent by weight based on said polyurethane.
Claim 34
Dependent Claim
110 words
A thermoplastic polyurethane characterized by high impact resistance, high flexural modulus, and a heat deflection temperature of at least 50° C. at 264 psi which comprises the product of reaction of: (a) 4,4'-methylenebis(phenyl isocyanate); (b) a polyether polyol having an average functionality of at least 1.9 and a molecular weight in the range of about 500 to about 20,000; and (c) at least one aliphatic diol chain extender having a molecular weight from about 50 to about 400; said polyurethane being further characterized in that the proportion by weight of said polyether polyol in said polyurethane is from about 4 to about 15 percent by weight based on said polyurethane.
Claim 35
Dependent Claim
40 words
A thermoplastic polyurethane according to claim 31 wherein said polyether polyol is a polyoxypropylene polyoxyethylene triol having a primary hydroxyl content of at least about 80 percent and a molecular weight in the range of about 2000 to about 20,000.
Claim 36
Dependent Claim
15 words
A thermoplastic polyurethane according to claim 31 wherein said polyether polyol is a polytetramethylene glycol.
Claim 37
Dependent Claim
89 words
A thermoplastic polyurethane according to claims 31, 32 or 33 wherein said chain extender is selected from the class consisting of 1,4-butanediol, neopentyl glycol, 1,6-hexanediol, 1,4-cyclohexanedimethanol, the product obtained by reacting 1,4-cyclohexanedimethanol with caprolactone in the mole ratio of from about 0.01 to about 2 moles of caprolactone per mole of 1,4-cyclohexanedimethanol, and the product obtained by reacting adipic acid and 1,4-cyclohexanedimethanol in the mole ratio of from about 0.01 to about 0.8 mole of acid per mole of 1,4-cyclohexanedimethanol, and mixtures of two or more of said diols.
Claim 38
Dependent Claim
23 words
A thermoplastic polyurethane according to claim 31 wherein the 4,4'-methylenebis(phenyl isocyanate) is employed in admixture with a minor amount of the corresponding 2,4'-isomer.
Claim 39
Dependent Claim
38 words
A thermoplastic polyurethane according to claim 31 wherein the 4,4'-methylenebis(phenyl isocyanate) has been reacted previously with a minor amount of at least one aliphatic diol thereby to form a diisocyanate which is a stable liquid at ambient temperature.
Claim 40
Dependent Claim
51 words
A thermoplastic polyurethane according to claim 31 wherein said 4,4'-methylenebis(phenyl isocyanate) is employed in admixture with a minor amount of a 4,4'-methylenebis(phenyl isocyanate) which has been treated previously to convert a minor proportion thereof to the corresponding carbodiimide thereby to form a product which is a stable liquid at ambient temperature.
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) | 1986-03-14 | 1986-09-13 | 1987-03-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-03-14 | 1990-09-13 | 1991-03-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-03-14 | 1994-09-13 | 1995-03-15 | $7700.00 | Window Closed / Lapsed |