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US4221895A
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Thermally resistant thermosetting aromatic polymers containing pendant 1-alkynyl substituents
Assignee: Dow Chemical Co
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Filing: 1978-04-18
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Granted: 1980-09-09
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Expires: 1998-04-18
Abstract
Abstract Thermally resistant thermoset polymers are formed by heating a thermosetting aromatic prepolymer having at least two pendant alkynyl groups, e.g., a thermosetting prepolymer represented by the formula: ##STR1## The resulting thermoset polymers are sufficiently resistant to heat to be usefully employed as engine parts in the internal combustion engines of automobiles and the like.
Inventors
- 👤 Edmund P. Woo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 09:34
CPC Classifications
C; C08; C08G; C08G75/00; C08F; C08F38/00; C08G75/24; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31678; Y10T428/31681; Y10T428/31692
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
59 words
An aromatic thermosetting prepolymer consisting essentially of repeating units of the formula: --YAr-- wherein each Ar is independently an aromatic group essentially free of acyclic aliphatic carbon-to-carbon bonds provided that at least two of Ar have pendant 1-alkynyl substituents and each Y is independently ##STR19## said prepolymer being curable upon application of heat to form a heat-resistant thermoset polymer.
Claim 2
Dependent Claim
59 words
An aromatic thermosetting prepolymer consisting essentially of repeating units of the formula: --YAr-- wherein each Ar is independently an aromatic group essentially free of acyclic aliphatic carbon-to-carbon bonds provided that at least two of Ar have pendant 1-alkynyl substituents and each Y is independently ##STR19## said prepolymer being curable upon application of heat to form a heat-resistant thermoset polymer.
Claim 3
Dependent Claim
78 words
An aromatic thermosetting prepolymer represented by the formula: Ar--YAr].sub.n YAr wherein each Ar is independently an aromatic group essentially free of acyclic aliphatic carbon-to-carbon bonds provided that at least two of Ar have pendant 1-alkynyl substituents; each Y is independently: ##STR20## and n is zero or an integer from 1 to about 18, said prepolymer being curable upon the application of heat to form a thermoset polymer having thermal oxidative stability at temperatures up to about 250° C.
Claim 4
Dependent Claim
78 words
An aromatic thermosetting prepolymer represented by the formula: Ar--YAr].sub.n YAr wherein each Ar is independently an aromatic group essentially free of acyclic aliphatic carbon-to-carbon bonds provided that at least two of Ar have pendant 1-alkynyl substituents; each Y is independently: ##STR20## and n is zero or an integer from 1 to about 18, said prepolymer being curable upon the application of heat to form a thermoset polymer having thermal oxidative stability at temperatures up to about 250° C.
Claim 5
Dependent Claim
43 words
The prepolymer of claim 2 wherein each Ar is independently arylene or a divalent radical derived from a compound selected from the group consisting of phenolphthalein, phenolsulfonephthalein, phthalidene, fluorescein and phenolphthalimidene by reacting said compound with a diacid chloride and 1-alkynyl is ethynyl.
Claim 6
Dependent Claim
47 words
The prepolymer of claim 2 wherein each Ar of --YAr-- n is independently arylene or a divalent aromatic radical represented by one of the formulas: ##STR21## wherein each G in the foregoing formulas is independently thio, imino, oxo, methylene, carbonyloxy, sulfonyloxy or sulfinyloxy and 1-alkynyl is ethynyl.
Claim 7
Dependent Claim
77 words
The prepolymer of claim 2 represented by the formula: Ar.sub.3 --YAr.sub.1 -YAr.sub.2 --.sub.n YAr.sub.3 wherein each Ar 1 is independently arylene, each Ar 2 is independently a divalent aromatic group essentially free of acyclic aliphatic carbon-to-carbon bonds and, each Ar 3 is individually a monovalent aromatic group which is essentially free of acyclic, aliphatic carbon-to-carbon bonds and has a pendant ethynyl group, Y is carbonyloxy and n is zero or an integer from 1 to about 18.
Claim 8
Dependent Claim
35 words
The prepolymer of claim 5 wherein Ar 1 is phenylene; Ar 2 is a radical represented by the formula: ##STR22## Ar 3 is ar-ethynylphenyl and n is an integer from about 1 to about 18.
Claim 9
Dependent Claim
12 words
The prepolymer of claim 2 which is represented by the formula: ##STR23##
Claim 10
Dependent Claim
12 words
The prepolymer of claim 2 which is represented by the formula: ##STR24##
Claim 11
Dependent Claim
11 words
A thermoset polymer prepared by heating the prepolymer of claim 1.
Claim 12
Dependent Claim
14 words
The thermoset polymer of claim 9 in the form of an automobile engine part.
Claim 13
Dependent Claim
14 words
The thermoset polymer of claim 9 in the form of a high temperature adhesive.
Claim 14
Dependent Claim
13 words
The thermoset polymer of claim 9 in the form of an insulative film.
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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) | 1983-09-09 | 1984-03-10 | 1984-09-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-09-09 | 1988-03-10 | 1988-09-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-09-09 | 1992-03-10 | 1992-09-09 | $7700.00 | Window Closed / Lapsed |