Patent US4127542A successfully refreshed from Google Patents.
US4127542A
Expired / Lapsed
US
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Stabilization of polyester urethanes using organic epoxides
Assignee: Air Products and Chemicals Inc
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Filing: 1977-02-23
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Granted: 1978-11-28
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Expires: 1997-02-23
Abstract
Abstract A storage stable polyester based polyurethane composition is provided which contains from about 0.05 to 0.75 percent by weight of an organic epoxide compound which has a molecular weight of not less than 60.
Inventors
- 👤 Samuel Kaizerman
- 👤 Ajaib Singh
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 23:10
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/04; C08K5/15; C08K5/151; C08K5/1515; C08L; C08L63/00; C08L75/00; C08L75/04; C08L75/06; Y; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/19
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
235 words
A stable solid elastomeric urethane composition selected from the group consisting of (A) the reaction product of (1) a hydroxyl-terminated polyester, (2) an aliphatic diol, (3) optionally, a mixture of an aliphatic diol and a minor amount of an aliphatic polyol having a functionality greater than 2, (4) an aromatic diisocyanate in an amount essentially stoichiometrically equivalent to the amount of available hydroxy groups of said (1), (2) and (3), and (5) optionally, a catalyst, and (B) the reaction product of (a) an isocyanate-terminated prepolymer composition prepared by reacting a hydroxyl-terminated polyester with an aromatic diisocyanate in excess of the amount of available hydroxyl groups in said polyester and (b) a compound comprising (I) an aromatic diamine in an amount of from about 75 to about 130% of the amount stoichiometrically required to react with the available isocyanate groups of said (a) or (II) an aliphatic diol, or a mixture of an aliphatic diol and a minor amount of an aliphatic polyol having a functionality greater than 2, in an amount of from about 80 to about 110% of the amount required to react with the available isocyanate groups of said (a) said (A) and (B) containing from about 0.05 to about 0.75%, by weight, based on the weight of (A) or (a), of an organic epoxide compound having a molecular weight greater than 60 and no other functional groups reactive with the urethane components.
Claim 2
Dependent Claim
235 words
A stable solid elastomeric urethane composition selected from the group consisting of (A) the reaction product of (1) a hydroxyl-terminated polyester, (2) an aliphatic diol, (3) optionally, a mixture of an aliphatic diol and a minor amount of an aliphatic polyol having a functionality greater than 2, (4) an aromatic diisocyanate in an amount essentially stoichiometrically equivalent to the amount of available hydroxy groups of said (1), (2) and (3), and (5) optionally, a catalyst, and (B) the reaction product of (a) an isocyanate-terminated prepolymer composition prepared by reacting a hydroxyl-terminated polyester with an aromatic diisocyanate in excess of the amount of available hydroxyl groups in said polyester and (b) a compound comprising (I) an aromatic diamine in an amount of from about 75 to about 130% of the amount stoichiometrically required to react with the available isocyanate groups of said (a) or (II) an aliphatic diol, or a mixture of an aliphatic diol and a minor amount of an aliphatic polyol having a functionality greater than 2, in an amount of from about 80 to about 110% of the amount required to react with the available isocyanate groups of said (a) said (A) and (B) containing from about 0.05 to about 0.75%, by weight, based on the weight of (A) or (a), of an organic epoxide compound having a molecular weight greater than 60 and no other functional groups reactive with the urethane components.
Claim 3
Dependent Claim
29 words
A composition according to claim 1 wherein said aromatic diisocyanate is selected from the group consisting of 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate and isomeric mixtures thereof, 4,4'-methylenebis)phenylisocyanate) and 1,5-naphthalene diisocyanate.
Claim 4
Dependent Claim
12 words
A composition according to claim 1 wherein said reaction product is (B).
Claim 5
Dependent Claim
12 words
A composition according to claim 1 wherein said reaction product is (A).
Claim 6
Dependent Claim
25 words
A composition according to claim 3 wherein said polyester is poly(ethylene adipate), said aromatic diisocyanate is tolylene diisocyanate and said compound is an aromatic diamine.
Claim 7
Dependent Claim
15 words
A composition according to claim 5 wherein said aromatic diamine is 4,4'-methylenebis(o-chloroaniline) or 2,6-dichloro-p-phenylene diamine.
Claim 8
Dependent Claim
14 words
A composition according to claim 1 wherein said organic epoxide is epoxidized soybean oil.
Claim 9
Dependent Claim
16 words
A composition according to claim 1 wherein said epoxide compound is the diglycidyl ether of 4,4'-isopropylidenebisphenol.
Claim 10
Dependent Claim
16 words
A composition according to claim 1 wherein said epoxide compound is the diglycidyl ether of 1,4-butanediol.
Claim 11
Dependent Claim
37 words
A composition according to claim 4 wherein said polyester, aromatic diisocyanate and aliphatic diol are reacted together in a manner such that the ratio of isocyanate groups to the total hydroxyl groups is about 0.9 to 1.1.
Claim 12
Dependent Claim
12 words
A composition according to claim 10 wherein said aromatic diisocyanate is 4,4'-methylenebis(phenylisocyanate).
Claim 13
Dependent Claim
21 words
A composition according to claim 10 wherein said organic epoxide is added to the reaction mixture before the reaction is completed.
Claim 14
Dependent Claim
17 words
A composition according to claim 10 wherein said composition contains a catalytic amount of an organotin compound.
Claim 15
Dependent Claim
13 words
A composition according to claim 13 wherein said organotin compound is stannous octoate.
Claim 16
Dependent Claim
135 words
A process for the preparation of a solid elastomeric stable storage or thermally urethane composition which comprises (1) reacting a hydroxyl terminated polyester with a stoichiometric excess of an aromatic diisocyanate to produce an isocyanate-terminated prepolymer, (2) adding thereto from about 0.05 to about 0.75%, by weight, based on the weight of said prepolymer, of an organic epoxide compound having a molecular weight greater than 60, and no other functional groups reactive with the urethane components and (3) reacting the isocyanate-terminated prepolymer containing said epoxide compound with from about 75 to about 130 percent of the stoichiometrically required amount of an aromatic diamine or from about 80 to about 110 percent of the stoichiometrically required amount of an aliphatic diol, or a mixture of said diol and a polyol having a functionality greater than 2.
Claim 17
Dependent Claim
135 words
A process for the preparation of a solid elastomeric stable storage or thermally urethane composition which comprises (1) reacting a hydroxyl terminated polyester with a stoichiometric excess of an aromatic diisocyanate to produce an isocyanate-terminated prepolymer, (2) adding thereto from about 0.05 to about 0.75%, by weight, based on the weight of said prepolymer, of an organic epoxide compound having a molecular weight greater than 60, and no other functional groups reactive with the urethane components and (3) reacting the isocyanate-terminated prepolymer containing said epoxide compound with from about 75 to about 130 percent of the stoichiometrically required amount of an aromatic diamine or from about 80 to about 110 percent of the stoichiometrically required amount of an aliphatic diol, or a mixture of said diol and a polyol having a functionality greater than 2.
Claim 18
Dependent Claim
22 words
A process according to claim 15 wherein said epoxide compound comprises from about 0.1 to about 0.6%, by weight, of said prepolymer.
Claim 19
Dependent Claim
122 words
A process for the preparation of a storage or thermally stable urethane composition which comprises reacting together a hydroxyl terminated polyester, an aliphatic diol or mixture of an aliphatic diol and a polyol having a functionality greater than 2 and an aromatic diisocyanate at a temperature of about 100° C, adding to the reaction mixture from about 0.05 to about 0.75%, by weight, based on the weight of said reaction mixture, of an epoxide compound having a molecular weight greater than 60 and no other functional groups reactive with the urethane components, the ratio of the isocyanate groups to the total hydroxyl groups being in the range of about 0.9 to 1.1, and heating said reaction mixture further to provide a solid.
Claim 20
Dependent Claim
122 words
A process for the preparation of a storage or thermally stable urethane composition which comprises reacting together a hydroxyl terminated polyester, an aliphatic diol or mixture of an aliphatic diol and a polyol having a functionality greater than 2 and an aromatic diisocyanate at a temperature of about 100° C, adding to the reaction mixture from about 0.05 to about 0.75%, by weight, based on the weight of said reaction mixture, of an epoxide compound having a molecular weight greater than 60 and no other functional groups reactive with the urethane components, the ratio of the isocyanate groups to the total hydroxyl groups being in the range of about 0.9 to 1.1, and heating said reaction mixture further to provide a solid.
Claim 21
Dependent Claim
22 words
A process according to claim 17 wherein there is additionally added to said reaction mixture a catalytic amount of an organotin compound.
Claim 22
Dependent Claim
24 words
A process according to claim 18 wherein said aromatic diisocyanate is 4,4'-methylenebis(phenylisocyanate) and said aliphatic diol is 1,4-butanediol or the dihydroxyethyl ether of hydroquinone.
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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) | 1981-11-27 | 1982-05-29 | 1982-11-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-11-27 | 1986-05-29 | 1986-11-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-11-27 | 1990-05-29 | 1990-11-28 | $7700.00 | Window Closed / Lapsed |