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US4076945A Expired / Lapsed US ⏱️ 0.0 years remaining

Method for making urethane-terminated polycarbodiimides and products thereof

Assignee: Aerojet Rocketdyne Holdings Inc
•
Filing: 1977-02-24
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Granted: 1978-02-28
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Expires: 1997-02-24
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Abstract

Abstract This invention concerns a method of making a urethane-terminated polycarbodiimide and the product resulting therefrom wherein the product displays unique hydrolytic degradation stabilization properties for polyester urethane rubbers and peroxide cured hydrocarbon rubbers. The method involves reacting an arylene diisocyanate with a stoichiometric deficiency of a primary or secondary aliphatic alcohol containing no other isocyanate-reactive substituents, thereby converting less than all of the isocyanate groups to urethane groups, and thereafter admixing thereto a carbodiimide-forming catalyst to polymerize the unconverted isocyanate groups and form the urethane-terminated polycarbodiimide.

Inventors

  • 👤 Otto C. Elmer

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 17:34
CPC Classifications
C; C08; C08G; C08G18/00

Claims Analysis

Total Claims: 6
Claim 1
Independent Claim 161 words
A urethane-terminated polycarbodiimide prepared by: 1 reacting at a temperature of no more than about 50° C. an arylene diisocyanate in which the isocyanate groups are of unequal reactivity and being selected from the group consisting of toluene 2,4-diisocyanate, 2-methyl napthalene 1,5-diisocyanate, 3-methyl-4,4'-diisocyanatodiphenylmethane, 3-chloro-4,4'-diisocyanatodiphenylmethane, 3-methoxy-4,4'-diisocyanatodiphenylmethane, 2,4-diisocyanatochlorobenzene, cumene 2,4-diisocyanate, m-xylene 2,5-diisocyanate and 3,5-dimethylbiphenyl-4,4'-diisocyanate with a stoichiometric deficiency of a primary or secondary aliphatic alcohol selected from the group consisting of methyl alcohol, ethyl alcohol, isopropyl alcohol, secondary buyl alcohol, isoamyl alcohol, n-hexanol, cyclohexanol, 2-chloro-1-propanol, 2-octanol, methylphenylcarbinol, benzyl alcohol, diethylene glycol mono-n-butyl ether, cinnamyl alcohol and 2-ethyl hexanol to convert less than all of the isocyanate groups to urethane groups; 2 cooling the mixture to near room temperature; and 3 admixing therewith a carbodiimide-forming catalyst and polymerizing the partially urethane-terminated arylene diisocyanate to a urethane-terminated polycarbodiimide that exhibits a single N═C═N peak at 2130 cm. -1 and is free of other peaks in the 2000 to 2500 cm. -1 band under infra-red inspection.
Claim 2
Dependent Claim 161 words
A urethane-terminated polycarbodiimide prepared by: 1 reacting at a temperature of no more than about 50° C. an arylene diisocyanate in which the isocyanate groups are of unequal reactivity and being selected from the group consisting of toluene 2,4-diisocyanate, 2-methyl napthalene 1,5-diisocyanate, 3-methyl-4,4'-diisocyanatodiphenylmethane, 3-chloro-4,4'-diisocyanatodiphenylmethane, 3-methoxy-4,4'-diisocyanatodiphenylmethane, 2,4-diisocyanatochlorobenzene, cumene 2,4-diisocyanate, m-xylene 2,5-diisocyanate and 3,5-dimethylbiphenyl-4,4'-diisocyanate with a stoichiometric deficiency of a primary or secondary aliphatic alcohol selected from the group consisting of methyl alcohol, ethyl alcohol, isopropyl alcohol, secondary buyl alcohol, isoamyl alcohol, n-hexanol, cyclohexanol, 2-chloro-1-propanol, 2-octanol, methylphenylcarbinol, benzyl alcohol, diethylene glycol mono-n-butyl ether, cinnamyl alcohol and 2-ethyl hexanol to convert less than all of the isocyanate groups to urethane groups; 2 cooling the mixture to near room temperature; and 3 admixing therewith a carbodiimide-forming catalyst and polymerizing the partially urethane-terminated arylene diisocyanate to a urethane-terminated polycarbodiimide that exhibits a single N═C═N peak at 2130 cm. -1 and is free of other peaks in the 2000 to 2500 cm. -1 band under infra-red inspection.
Claim 3
Dependent Claim 11 words
The product of claim 1 wherein the carbodiimide-forming catalyst is 1-phenyl-3-methyl-3-phospholine-1-oxide.
Claim 4
Dependent Claim 15 words
The product of claim 1 wherein said reaction (1) is performed in an inert solvent.
Claim 5
Dependent Claim 22 words
The product of claim 1 wherein said arylene diisocyanate contains additionally blended therewith an arylene diisocyanate having isocyanate groups of equal reactivity.
Claim 6
Dependent Claim 36 words
The product of claim 1 where in said reaction (1) the amount of alcohol is such that the ratio of alcohol hydroxyl groups to isocyanate groups is in the range of from about 1:4 to 1:40.

References Cited (Backward Citations)

US3115479A Cited
US2941966A Cited
US2969386A Cited
US3502722A Cited
GB1086091A Cited
US3969288A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-02-27 1981-08-29 1982-02-28 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-02-27 1985-08-29 1986-02-28 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-02-27 1989-08-29 1990-02-28 $7700.00 Window Closed / Lapsed

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