US4375536A
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Polyphenylquinoxalines containing pendant phenylethynyl and ethynyl groups
Assignee: National Aeronautics and Space Administration
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Filing: 1981-11-12
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Granted: 1983-03-01
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Expires: 2001-11-12
Abstract
Abstract Poly(phenylquinoxaline) prepolymers containing pendant phenylethynyl and ethynyl groups are disclosed along with the process for forming these polymers. Novel monomers and the process for producing same that are employed to prepare the novel polymers are also disclosed.
Inventors
- 👤 with respect to an invention of Mark Hans M. Acting Administrator of the National Aeronautics and Space Administration
- 👤 Paul M. Hergenrother
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 16:00
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/0683; C08G73/0694
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
64 words
A poly(phenylquinoxaline) polymer consisting essentially of repeating units and synthesized from the reaction of (I) aromatic bis(o-diamines) with (II) aromatic bis(α-diketones) and (III) aromatic bis(ethynylphenyl-α-diketones) or aromatic bis(phenylethynyl-α-diketones) according to the reaction scheme: ##STR12## where Ar is aromatic and selected from the group consisting of ##STR13## Ar' is ##STR14## X is --C.tbd.CH, ##STR15## Y is 5-100% X and 0-95% H, and, n is 20-10,000.
Claim 2
Dependent Claim
64 words
A poly(phenylquinoxaline) polymer consisting essentially of repeating units and synthesized from the reaction of (I) aromatic bis(o-diamines) with (II) aromatic bis(α-diketones) and (III) aromatic bis(ethynylphenyl-α-diketones) or aromatic bis(phenylethynyl-α-diketones) according to the reaction scheme: ##STR12## where Ar is aromatic and selected from the group consisting of ##STR13## Ar' is ##STR14## X is --C.tbd.CH, ##STR15## Y is 5-100% X and 0-95% H, and, n is 20-10,000.
Claim 3
Dependent Claim
9 words
The polymer of claim 1 wherein Ar is ##STR16##
Claim 4
Dependent Claim
9 words
The polymer of claim 1 wherein Ar is ##STR17##
Claim 5
Dependent Claim
9 words
The polymer of claim 1 wherein Ar is ##STR18##
Claim 6
Dependent Claim
9 words
The polymer of claim 1 wherein Ar' is ##STR19##
Claim 7
Dependent Claim
9 words
The polymer of claim 1 wherein Ar' is ##STR20##
Claim 8
Dependent Claim
9 words
The polymer of claim 1 wherein Ar' is ##STR21##
Claim 9
Dependent Claim
9 words
The polymer of claim 1 wherein Ar' is ##STR22##
Claim 10
Dependent Claim
9 words
The polymer of claim 1 wherein Y is --C.tbd.CH.
Claim 11
Dependent Claim
9 words
The polymer of claim 1 wherein Y is ##STR23##
Claim 12
Dependent Claim
9 words
The polymer of claim 1 wherein Y is ##STR24##
Claim 13
Dependent Claim
9 words
The polymer of claim 1 wherein Y is ##STR25##
Claim 14
Dependent Claim
22 words
The polymer of claim 1 where Y is at least 5 mole percent of --C.tbd.CH and the remaining mole percentage being H.
Claim 15
Dependent Claim
21 words
The polymer of claim 1 wherein Y is at least 5 mole percent ##STR26## and the remaining mole percentage being H.
Claim 16
Dependent Claim
21 words
The polymer of claim 1 wherein Y is at least 5 mole percent ##STR27## and the remaining mole percentage being H.
Claim 17
Dependent Claim
21 words
The polymer of claims 1 wherein Y is at least 5 mole percent ##STR28## and the remaining mole percentage being H.
Claim 18
Dependent Claim
29 words
The product produced by subjecting polymers of claim 1 to temperatures in the range of 150°-475° C. for approximately 0.5 hour, wherein said polymers under go crosslinking via Y.
Claim 19
Dependent Claim
26 words
A polyphenylquinoxaline polymer consisting of repeating units and synthesized according to the reaction: ##STR29## where X is 0-95% H and 5-100% C.tbd.CH, and, n is 20-10,000.
Claim 20
Dependent Claim
26 words
A polyphenylquinoxaline polymer consisting of repeating units and synthesized according to the reaction: ##STR29## where X is 0-95% H and 5-100% C.tbd.CH, and, n is 20-10,000.
Claim 21
Dependent Claim
35 words
A polyphenylquinoxaline polymer consisting of repeating units and synthesized according to the reaction: ##STR30## where Y is 0-95% H and 5-100% of a member selected from the group consisting of: ##STR31## and, n is 20-10,000.
Claim 22
Dependent Claim
35 words
A polyphenylquinoxaline polymer consisting of repeating units and synthesized according to the reaction: ##STR30## where Y is 0-95% H and 5-100% of a member selected from the group consisting of: ##STR31## and, n is 20-10,000.
Claim 23
Dependent Claim
49 words
A polyphenylquinoxaline polymer consisting essentially of repeating units having the formula: ##STR32## where Ar is a tetravalent aromatic group, Ar' is selected from the group consisting of ##STR33## Y is 0-95% H and 5-100% of a member selected from the group consisting of --C.tbd.CH, ##STR34## and, n is 20-10,000.
Claim 24
Dependent Claim
49 words
A polyphenylquinoxaline polymer consisting essentially of repeating units having the formula: ##STR32## where Ar is a tetravalent aromatic group, Ar' is selected from the group consisting of ##STR33## Y is 0-95% H and 5-100% of a member selected from the group consisting of --C.tbd.CH, ##STR34## and, n is 20-10,000.
Claim 25
Independent Claim
107 words
A method of synthesizing novel polymers comprising: combining stoichiometric quantities of a bis(1,2-diketone) monomer in a solvent selected from a group consisting of chloroform, sym-tetrachloroethane, m-cresol, and mixtures of m-cresol and xylene and m-cresol and toluene at a concentration of 10 to 30% weight/volume with powdered 3,3'4,4'-tetraaminobiphenyl stirring the mixture for 4-6 hours at ambient temperature and thereafter stirring for one hour at 90° C. to recover an amber colored viscous solution, doctoring a portion of this solution onto a glass plate and stage drying to a final temperature of approximately 110° C. under vaccum for 4-6 hours to yield a transparent yellow film fingernail creaseable polymer.
Claim 26
Independent Claim
107 words
A method of synthesizing novel polymers comprising: combining stoichiometric quantities of a bis(1,2-diketone) monomer in a solvent selected from a group consisting of chloroform, sym-tetrachloroethane, m-cresol, and mixtures of m-cresol and xylene and m-cresol and toluene at a concentration of 10 to 30% weight/volume with powdered 3,3'4,4'-tetraaminobiphenyl stirring the mixture for 4-6 hours at ambient temperature and thereafter stirring for one hour at 90° C. to recover an amber colored viscous solution, doctoring a portion of this solution onto a glass plate and stage drying to a final temperature of approximately 110° C. under vaccum for 4-6 hours to yield a transparent yellow film fingernail creaseable polymer.
Claim 27
Dependent Claim
27 words
The method of claim 21 wherein the bis(1,2-diketone) monomer is selected from the group of monomers consisting of: 4-(4-trimethylsilylethynylphenoxy)benzil, 4-(4-ethynylphenoxy)benzil, 4-4'-oxybis(4"-trimethylsilylethynylbenzil), 4,4'-oxybis(4"-ethynylbenzil), 1,3-bis[4-(4-trimethylsilylethynylphenoxy)phenylglyoxylyl]benzene, 1,3-bis[4-(4-ethynylphenoxy)phenylglyoxylyl]benzene, 4,4'-oxybis(4"-phenylethynylbenzil), and 1,3-bis[4-(4-phenylethynylphenoxy)phenylglyoxylyl]benzene.
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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) | 1986-02-28 | 1986-08-30 | 1987-03-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-02-28 | 1990-08-30 | 1991-03-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-02-28 | 1994-08-30 | 1995-03-01 | $7700.00 | Window Closed / Lapsed |