US4546167A
Expired / Lapsed
US
⏱️ 0.0 years remaining
P-TMXDI Polyurethane elastomers with good compression set properties
Assignee: Wyeth Holdings LLC
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Filing: 1984-07-30
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Granted: 1985-10-08
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Expires: 2004-07-30
Abstract
Abstract Polyurethane elastomer compositions, having a compression set less than or equal to about 40% are disclosed. These polyurethane elastomer compositions comprise the reaction product of: (a) A polyurethane prepolymer having terminally reactive isocyanate groups and formed as a reaction product of polymeric diol with a stoichiometric excess of p-tetramethylxylene diisocyanate (p-TMXDI); with (b) A curatively effective amount of a curative selected from the group consisting of: diethyltoluenediamine (DETDA), 2,4-bis (p-aminobenzyl)aniline (BABA), and mixtures thereof; and (c) Optionally, from about 0.01% to about 2% by weight of catalyst, based on the weight of curative. These polyurethane elastomers are used in molded articles which are to be used under load as in machine rolls and wheels.
Inventors
- 👤 Eugene Y. C. Chang
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 07:21
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/10; C08G18/12; C08G18/70; C08G18/72; C08G18/74; C08G18/76; C08G18/7614; C08G18/7628; C08G18/765; C08G18/16
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
84 words
A polyurethane elastomer composition, having a compression set less than or equal to about 40%, comprising the reaction product of: (a) a polyurethane prepolymer having terminally reactive isocyanate groups and formed as a reaction product of polymeric diol with a stoichiometric excess of p-tetramethylxylene diisocyanate with (b) a curatively effective amount of a curative selected from the group consisting of: diethyltoluenediamine, 2,4-bis(p-aminobenzyl)aniline, and mixtures thereof; and (c) optionally, from about 0.01% to about 2% by weight of catalyst, based on the weight of curative.
Claim 2
Dependent Claim
84 words
A polyurethane elastomer composition, having a compression set less than or equal to about 40%, comprising the reaction product of: (a) a polyurethane prepolymer having terminally reactive isocyanate groups and formed as a reaction product of polymeric diol with a stoichiometric excess of p-tetramethylxylene diisocyanate with (b) a curatively effective amount of a curative selected from the group consisting of: diethyltoluenediamine, 2,4-bis(p-aminobenzyl)aniline, and mixtures thereof; and (c) optionally, from about 0.01% to about 2% by weight of catalyst, based on the weight of curative.
Claim 3
Dependent Claim
22 words
An elastomer of claim 1 wherein the ratio of equivalents of p-tetramethylxylene diisocyanate to polymeric diol is about 2:1 to about 5:1.
Claim 4
Dependent Claim
22 words
An elastomer of claim 1 wherein the ratio of equivalents of p-tetramethylxylene diisocyanate to polymeric diol is about 2.5:1 to about 4.5:1.
Claim 5
Dependent Claim
22 words
An elastomer of claim 1 wherein the ratio of equivalents of p-tetramethylxylene diisocyanate to polymeric diol is about 3.0:1 to about 3.5:1.
Claim 6
Dependent Claim
71 words
An elastomer of claim 1 wherein said diol is selected from the group consisting of: (i) a polyether selected from the group consisting of polytetramethylene ether glycol; polypropylene ether glycol; polypropylene-polyethylene oxide ether glycol; and mixtures thereof; (ii) a polyester selected from the group consisting of polyethylene adipate; polypropylene adipate; poly(ethylene-propylene) adipate; polybutylene adipate; polyhexamethylene adipate; polycaprolactone; and mixtures thereof; and (iii) a compatible mixture of polyether diols and polyester diols.
Claim 7
Dependent Claim
12 words
An elastomer of claim 5 wherein said diol is polytetramethylene ether glycol.
Claim 8
Dependent Claim
11 words
An elastomer of claim 5 wherein said diol is polyethylene adipate.
Claim 9
Dependent Claim
26 words
An elastomer of claim 1 wherein said prepolymer has an isocyanate content of about 2.0 to about 9.0 wt %, based on the weight of prepolymer.
Claim 10
Dependent Claim
23 words
An elastomer of claim 1 wherein said curative is present in amount of from about 75% to about 110% of the stoichiometric amount.
Claim 11
Dependent Claim
10 words
An elastomer of claim 1 wherein said curative is diethyltoluenediamine.
Claim 12
Dependent Claim
10 words
An elastomer of claim 1 wherein said curative is 2,4-bis(p-aminobenzyl)aniline.
Claim 13
Dependent Claim
26 words
An elastomer of claim 1 wherein said prepolymer has an isocyanate content of about 4.5 to about 7.0 wt %, based on the weight of prepolymer.
Claim 14
Dependent Claim
198 words
A polyurethane elastomer composition, having a compression set less than or equal to about 40%, comprising the reaction product of: (a) A polyurethane prepolymer having terminally reactive isocyanate groups and formed as a reaction product of polymeric diol selected from the group consisting of: (i) a polyether selected from the group consisting of polytetramethylene ether glycol; polypropylene ether glycol; polypropylene-polyethylene oxide ether glycol; and mixtures thereof; (ii) a polyester selected from the group consisting of polyethylene adipate; polypropylene adipate; poly(ethylenepropylene) adipate; polybutylene adipate; polyhexamethylene adipate; polycaprolactone; and mixtures thereof; and (iii) a compatible mixture of polyether diols and polyester diols; with a stoichiometric excess of p-tetramethylxylene diisocyanate, said prepolymer having an isocyanate content of about 2.0 to about 9.0 wt %, based on the weight of prepolymer; with (b) Between about 75% and about 110% of the stoichiometric amount of a curative selected from the group consisting of: -diethyltoluenediamine, 2,4-bis-(p-aminobenzyl)aniline and mixtures thereof; and (c) Optionally, from about, 0.01% to about 2% by weight of catalyst, based on the weight of curative, said catalyst being selected from the group consisting of mono and dicarboxylic acids, metal salts of mono and dicarboxylic acids, carboxylic acid anhydrides and tertiary amines.
Claim 15
Dependent Claim
198 words
A polyurethane elastomer composition, having a compression set less than or equal to about 40%, comprising the reaction product of: (a) A polyurethane prepolymer having terminally reactive isocyanate groups and formed as a reaction product of polymeric diol selected from the group consisting of: (i) a polyether selected from the group consisting of polytetramethylene ether glycol; polypropylene ether glycol; polypropylene-polyethylene oxide ether glycol; and mixtures thereof; (ii) a polyester selected from the group consisting of polyethylene adipate; polypropylene adipate; poly(ethylenepropylene) adipate; polybutylene adipate; polyhexamethylene adipate; polycaprolactone; and mixtures thereof; and (iii) a compatible mixture of polyether diols and polyester diols; with a stoichiometric excess of p-tetramethylxylene diisocyanate, said prepolymer having an isocyanate content of about 2.0 to about 9.0 wt %, based on the weight of prepolymer; with (b) Between about 75% and about 110% of the stoichiometric amount of a curative selected from the group consisting of: -diethyltoluenediamine, 2,4-bis-(p-aminobenzyl)aniline and mixtures thereof; and (c) Optionally, from about, 0.01% to about 2% by weight of catalyst, based on the weight of curative, said catalyst being selected from the group consisting of mono and dicarboxylic acids, metal salts of mono and dicarboxylic acids, carboxylic acid anhydrides and tertiary amines.
Claim 16
Dependent Claim
22 words
An elastomer of claim 13 wherein the ratio of equivalents of p-tetramethylxylene diisocyanate to polymeric diol is about 2:1 to about 5:1.
Claim 17
Dependent Claim
22 words
An elastomer of claim 13 wherein the ratio of equivalents of p-tetramethylxylene diisocyanate to polymeric diol is about 2.5:1 to about 4.5:1.
Claim 18
Dependent Claim
22 words
An elastomer of claim 13 wherein the ratio of equivalents of p-tetramethylxylene diisocyanate to polymeric diol is about 3.0:1 to about 3.5:1.
Claim 19
Dependent Claim
12 words
An elastomer of claim 13 wherein said diol is polytetramethylene ether glycol.
Claim 20
Dependent Claim
11 words
An elastomer of claim 13 wherein said diol is polyethylene adipate.
Claim 21
Dependent Claim
10 words
An elastomer of claim 13 wherein said curative is diethyltoluenediamine.
Claim 22
Dependent Claim
10 words
An elastomer of claim 13 wherein said curative is 2,4-bis(p-aminobenzyl)aniline.
Claim 23
Dependent Claim
26 words
An elastomer of claim 13 wherein said prepolymer has an isocyanate content of about 4.5 to about 7.0 wt %, based on the weight of prepolymer.
Claim 24
Dependent Claim
35 words
An elastomer of claim 13 wherein the ratio of equivalents of p-tetramethylxylene diisocyanate to polymeric diol is about 2:1 to about 5:1 and wherein said isocyanate content is about 4.5 to about 7.0 wt %.
Claim 25
Dependent Claim
32 words
An elastomer of claim 13 wherein said diol is polytetramethylene ether glycol and said curative is diethyltoluenediamine or 2,4-bis(p-aminobenzyl)aniline, or wherein said diol is polyethylene adipate and said curative is diethyltoluene diamine.
Claim 26
Dependent Claim
11 words
An article of manufacture made from the composition of claim 1.
Claim 27
Dependent Claim
11 words
An article of manufacture made from the composition of claim 13.
Claim 28
Independent Claim
88 words
A method of making a polyurethane elastomer having a compression set of less than or equal to about 40% comprising the steps of reacting: (a) A polyurethane prepolymer having terminally reactive isocyanate groups and formed as a reaction product of polymeric diol with a stoichiometric excess of p-tetramethylxylene diisocyanate; with (b) A curatively effective amount of a curative selected from the group consisting of: diethyltoluenediamine, 2,4-bis(p-aminobenzyl)aniline, and mixtures thereof; and (c) optionally, from about 0.01% to about 2% by weight of catalyst based on the weight of curative.
Claim 29
Independent Claim
88 words
A method of making a polyurethane elastomer having a compression set of less than or equal to about 40% comprising the steps of reacting: (a) A polyurethane prepolymer having terminally reactive isocyanate groups and formed as a reaction product of polymeric diol with a stoichiometric excess of p-tetramethylxylene diisocyanate; with (b) A curatively effective amount of a curative selected from the group consisting of: diethyltoluenediamine, 2,4-bis(p-aminobenzyl)aniline, and mixtures thereof; and (c) optionally, from about 0.01% to about 2% by weight of catalyst based on the weight of curative.
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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) | 1988-10-07 | 1989-04-08 | 1989-10-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-10-07 | 1993-04-08 | 1993-10-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-10-07 | 1997-04-08 | 1997-10-08 | $7700.00 | Window Closed / Lapsed |