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US4059570A Expired / Lapsed US ⏱️ 0.0 years remaining

Polythioether polyurethanes and their preparation

Assignee: ExxonMobil Technology and Engineering Co
•
Filing: 1976-05-04
•
Granted: 1977-11-22
•
Expires: 1996-05-04
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Abstract

Abstract Novel polythioether polyurethanes of superior thermal and oxidative aging stability are prepared from polythioether dithiols derived from addition of dithiols to acetylenes under free radical conditions. These polythioether dithiols having alkyl branching contain the divalent alkylene groups derived from their dithiol and acetylene monomer components in a regularly alternating manner. This dithiol is reacted with an epoxide with an amine catalyst to form a polythioether diol of the formula ##STR1## wherein R is a C 1 -C 30 divalent organic radical, R' is selected from the group consisting of H, C 1 -C 30 alkyl, C 2 -C 30 alkenyl, C 2 -C 30 alkynyl, C 7 -C 20 aralkyl and mixtures thereof, provided that either R has a branched structure or R' is alkyl, R" is H or methyl and n is 2 to 1000. These polythioether diols are chain extended and crosslinked via reactions with organic diisocyanates of the formula R'" (NCO) 2 to yield polythioether polyurethanes of the repeating structure: ##STR2## wherein R, R', R" and n are as defined above and R"' is phenylene, tolylene, xylylene, diphenylmethane, chlorophenylene and C 2 to C 12 polymethylene. These polythioether polyurethanes possess superior thermal and oxidative aging stability.

Inventors

  • 👤 Alexis A. Oswald

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 22:53
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/52; C08G75/00; C08G75/02; C08G75/04; C08G75/045

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 120 words
Process for the preparation of polythioether polyurethanes comprising reacting a polythioether diol of the formula ##STR38## wherein R" is hydrogen or methyl, R is a C 1 to C 30 divalent organic radical; R' is selected from the group consisting of H, C 1 -C 30 alkyl, C 2 -C 30 alkenyl, C 2 -C 30 alkynyl, C 7 -C 20 aralkyl and mixtures thereof, providing that either R has a branched structure or R' is alkyl and n is 2 to 1000, with a diisocyanate of the formula R'"(NCO).sub.2 wherein R'" is phenylene, tolylene, xylylene, diphenylmethane, chlorophenylene, C 2 to C 16 polymethylene and polymethylene groups interrupted by thioether sulfur, to yield a product of the repeating structure ##STR39##
Claim 2
Dependent Claim 120 words
Process for the preparation of polythioether polyurethanes comprising reacting a polythioether diol of the formula ##STR38## wherein R" is hydrogen or methyl, R is a C 1 to C 30 divalent organic radical; R' is selected from the group consisting of H, C 1 -C 30 alkyl, C 2 -C 30 alkenyl, C 2 -C 30 alkynyl, C 7 -C 20 aralkyl and mixtures thereof, providing that either R has a branched structure or R' is alkyl and n is 2 to 1000, with a diisocyanate of the formula R'"(NCO).sub.2 wherein R'" is phenylene, tolylene, xylylene, diphenylmethane, chlorophenylene, C 2 to C 16 polymethylene and polymethylene groups interrupted by thioether sulfur, to yield a product of the repeating structure ##STR39##
Claim 3
Dependent Claim 9 words
The process of claim 1 wherein R'" is hexamethylene.
Claim 4
Dependent Claim 9 words
The process of claim 1 wherein R" is hydrogen.
Claim 5
Dependent Claim 9 words
The process of claim 1 wherein R" is methyl.
Claim 6
Dependent Claim 103 words
Polythioether polyurethane polymers of the repeating structure: ##STR40## and their derivatives crosslinked via diisocyanate reactions, wherein R" is hydrogen or methyl, R is a C 1 to C 30 divalent organic radical, R' is selected from the group consisting of H, C 1 -C 30 alkyl, C 2 -C 30 alkenyl, C 2 -C 30 alkynyl, C 7 -C 20 aralkyl and mixtures thereof, providing that either R has a branched structure or R' is alkyl and n is 2 to 1000, and R'" is phenylene, tolylene, xylylene, diphenylmethane, chlorophenylene, C 2 to C 16 polymethylene and polymethylene groups interrupted by thioether sulfur.
Claim 7
Dependent Claim 103 words
Polythioether polyurethane polymers of the repeating structure: ##STR40## and their derivatives crosslinked via diisocyanate reactions, wherein R" is hydrogen or methyl, R is a C 1 to C 30 divalent organic radical, R' is selected from the group consisting of H, C 1 -C 30 alkyl, C 2 -C 30 alkenyl, C 2 -C 30 alkynyl, C 7 -C 20 aralkyl and mixtures thereof, providing that either R has a branched structure or R' is alkyl and n is 2 to 1000, and R'" is phenylene, tolylene, xylylene, diphenylmethane, chlorophenylene, C 2 to C 16 polymethylene and polymethylene groups interrupted by thioether sulfur.
Claim 8
Dependent Claim 9 words
The product of claim 5 wherein R'" is hexamethylene.
Claim 9
Dependent Claim 9 words
The product of claim 5 wherein R" is hydrogen.
Claim 10
Dependent Claim 9 words
The product of claim 5 wherein R" is methyl.

References Cited (Backward Citations)

US3386963A Cited
US3647766A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-11-21 1981-05-23 1981-11-22 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-11-21 1985-05-23 1985-11-22 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-11-21 1989-05-23 1989-11-22 $7700.00 Window Closed / Lapsed

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