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US4288577A Expired / Lapsed US ⏱️ 0.0 years remaining

Novel urethanediols and polyurethanes therefrom

Assignee: UNIROYAL
•
Filing: 1979-12-14
•
Granted: 1981-09-08
•
Expires: 1999-12-14
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Abstract

Abstract Reaction of a large excess of 1,4-butanediol with methylenebis (4-phenyl isocyanate) gives a mixture of urethanediols which is a suitable curing agent for isocyanate-terminated polyurethane prepolymers, especially prepolymers made from methylenebis (4-phenyl isocyanate) and polyols. It is desirable to have a urethanediol mixture in which at least about 88 weight percent consists of the reaction product of 2 moles of 1,4-butanediol with 1 mole of the diisocyanate, about 10 weight percent of the reaction product of 3 moles of 1,4-butanediol with 2 moles of the diisocyanate, and no more than about 2 weight percent of 1,4-butanediol. The novel cured polyurethanes have higher hardness and better overall physical properties than methylenebis-(4-phenyl isocyanate)-based polyurethanes cured with conventional commercial diols providing "hard" cured products.

Inventors

  • 👤 Herbert F. McShane, Jr.

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-25 08:59
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/10

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 38 words
A composition of matter selected from the group consisting of the urethanediol having the following formula (1) ##STR2## the urethanediol having the following formula (2) ##STR3## and a mixture of urethanediols having the above formulas (1) and (2).
Claim 2
Dependent Claim 38 words
A composition of matter selected from the group consisting of the urethanediol having the following formula (1) ##STR2## the urethanediol having the following formula (2) ##STR3## and a mixture of urethanediols having the above formulas (1) and (2).
Claim 3
Dependent Claim 32 words
A composition of matter of claim 1 consisting essentially of a mixture of urethanediols of formulas (1) and (2) wherein the urethanediol of formula (2) constitutes about 8-12% of the total weight.
Claim 4
Dependent Claim 28 words
A composition of matter of claim 2 wherein, in addition to the urethanediols of formulas (1) and (2), there is also present about 0-3% by weight of 1,4-butanediol.
Claim 5
Dependent Claim 36 words
A composition of matter of claim 3 consisting essentially of about 88-89% of the urethanediol of formula (1), about 10% of the urethanediol of formula (2), and about 1-2% of 1,4-butanediol, all percentages being by weight.
Claim 6
Dependent Claim 51 words
In a process for curing an isocyanate-terminated polyurethane prepolymer with a diol, the improvement of using as the diol a mixture of about 85-92 weight percent of the diol of formula (1) ##STR4## about 8-12 weight percent of the diol of formula (2) ##STR5## and about 0-3 weight percent of 1,4-butanediol.
Claim 7
Dependent Claim 51 words
In a process for curing an isocyanate-terminated polyurethane prepolymer with a diol, the improvement of using as the diol a mixture of about 85-92 weight percent of the diol of formula (1) ##STR4## about 8-12 weight percent of the diol of formula (2) ##STR5## and about 0-3 weight percent of 1,4-butanediol.
Claim 8
Dependent Claim 36 words
The improvement of claim 5 wherein the diol of formula (2) is present in the mixture in an amount of about 10 weight percent, and 1,4-butanediol in an amount of at most about 2 weight percent.
Claim 9
Dependent Claim 18 words
The improvement of claim 5 wherein the prepolymer is a reaction product of a polyol with methylenebis(4-phenyl isocyanate).
Claim 10
Dependent Claim 12 words
A cured polyurethane prepared according to the improved process of claim 7.

References Cited (Backward Citations)

US2703810A Cited
GB761395A Cited
US2802022A Cited
JPS4738077U Cited
US4120834A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-09-07 1985-03-09 1985-09-08 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-09-07 1989-03-09 1989-09-08 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-09-07 1993-03-09 1993-09-08 $7700.00 Window Closed / Lapsed

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