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Polyphenylquinoxalines containing latent crosslinking groups

Assignee: Boeing Co
•
Filing: 1973-07-23
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Granted: 1974-12-03
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Expires: 1993-07-23
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Abstract

Abstract Disclosed are polyphenylquinoxalines containing latent crosslinking groups, such as -CN, -OCN, -CNO and -C*CH groups, and processes for preparing and using same. These polymers can be prepared by reacting a bis(o-diamine) and a bis(1,2-dicarbonyl) compound containing latent crosslinking groups in a solvent such as m-cresol, anisole or chloroform. Alternatively, an aromatic bis(o-diamine) can be reacted with a bis (1,2-dicarbonyl) compound containing reactive hydroxyl groups, the resulting hydroxyl-containing polyphenylquinoxalines being then further reacted in a solvent such as N,N-dimethylacetamide with a modifying agent such as cyanogen bromide to provide polyphenylquinoxalines containing -OCN groups. Upon exposure of these polymers to elevated temperatures (optionally in the presence of a catalyst), they undergo crosslinking via the latent crosslinking groups, and become less thermoplastic or essentially non-thermoplastic. The polyphenylquinoxalines of this invention are particularly useful as adhesives, laminating resins, protective coatings, films and membranes for employment in environments requiring high chemical and thermal stability.

Inventors

  • 👤 P Hergenrother

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 20:48
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/27; C07C45/28; C08; C08G; C08G73/00; C08G73/06; C08G73/0622; C08G73/0638

Claims Analysis

Total Claims: 40
Claim 1
Independent Claim 6 words
POLYMERS COMPRISING UNITS OF THE FORMULA
Claim 2
Dependent Claim 6 words
POLYMERS COMPRISING UNITS OF THE FORMULA
Claim 3
Dependent Claim 16 words
Polymers of claim 1 wherein R2 and R3 are individually selected from the group consisting of
Claim 4
Dependent Claim 15 words
Polymers of claim 2 wherein m is 1; and X is -O-, -S- or -CH2-.
Claim 5
Dependent Claim 20 words
Polymers of claim 2 wherein R4 is -OCN; m is 1; X is -O- and R5 is -CN or -OCN.
Claim 6
Dependent Claim 46 words
Polymers of claim 1 wherein Ar is a tetravalent 1,2,-4,5-benzene, 3,3''4,4''-biphenyl, 3,3''4,4''-diphenyl ether, 3,3''4,-4''-thiodiphenyl ether, 3,3'',4,4''-diphenylsulfoxide, 3,3'',4,4''-diphenylsulfone, 3,3''4,4''-benzophenone, 3,3''4,4''-diphenylmethane, 3,3'',4,4''-diphenylisopropane, 3,3''4,4''-diphenylmethanol, 1,2,5,6-naphthalene, or 2,3,6,7-naphthalene group; and R1 is p-phenylene, m-phenylene, p,p''-biphenylene, p,p''-oxydiphenylene, p,p''-thiodiphenylene, p,p''-sulfonyldiphenylene, p,p''-carbonyldiphenylene, p,p''-methylenediphenylene, p,p''-isopropylidenediphenylene, a 2-pyridinediyl, a 2-pyrrole diyl, 2, 7-dibenzofurandiyl or 2,6-naphthalene.
Claim 7
Dependent Claim 16 words
Polymers of claim 5 wherein R2 and R3 are individually selected from the group consisting of
Claim 8
Dependent Claim 15 words
Polymers of claim 6 wherein m is 1; and X is -O-, -S- or -CH2-.
Claim 9
Dependent Claim 20 words
Polymers of claim 6 wherein R is -OCN; m is 1; X is -O- and R5 is -CN or -OCN.
Claim 10
Dependent Claim 33 words
Polymers of claim 1 wherein Ar is a tetravalent 1,2,-4,5-benzene, 3,3'',4,4''-biphenyl, 3,3'',4,4''-diphenyl ether, 3,3'',4,4''-thiodiphenyl ether, 3,3'',4,4''-diphenylsulfoxide, 3,3'',4,4''-diphenylsulfone, 3,3'',4,4''-benzophenone, 3,3'',4,4''-diphenylmethane, or 3,3'',-4,4''-diphenylmethanol group; and R1 is p-phenylene, m-phenylene, p,p''-biphenylene, p,p''-oxydiphenylene, p,p''-thiodiphenylene, p,p''-carbonyldiphenylene, or p,p''-methylenediphenylene.
Claim 11
Dependent Claim 16 words
Polymers of claim 9 wherein R2 and R3 are individually selected from the group consisting of
Claim 12
Dependent Claim 15 words
Polymers of claim 10 wherein m is 1; and X is -O-, -S- or -CH2-.
Claim 13
Dependent Claim 19 words
Polymers of claim 10 wherein R4 is -OCN; m is 1; X is -O-and R5 is -CN or -OCN.
Claim 14
Dependent Claim 28 words
Polymers of claim 1 wherein Ar is a tetravalent 3,3'',4, 4''biphenyl, 3,3'',4,4''-diphenyl ether, 3,3'',4,4''-thiodiphenyl ether, 3,3'',4,4''benzophenone or 3,3'',4,4''-diphenylmethane group; and R1 is p-phenylene, m-phenylene, p,p''-oxydiphenylene, p,p''-thiodiphenylene or p,p''-methylenediphenylene.
Claim 15
Dependent Claim 16 words
Polymers of claim 11 wherein R2 and R3 are individually selected from the group consisting of
Claim 16
Dependent Claim 15 words
Polymers of claim 14 wherein m is 1; and X is -O-, -S- or -CH2-.
Claim 17
Dependent Claim 19 words
Polymers of claim 14 wherein R4 is -OCN; m is 1; X is -O-and R5 is -CN or -OCN.
Claim 18
Dependent Claim 21 words
Polymers of claim 1 wherein Ar is a 3,3'',4,4''-biphenyl or 3, 3'',4,4''-benzophenone group; and R1 is a m-phenylene or p,p''-oxydiphenylene group.
Claim 19
Dependent Claim 16 words
Polymers of claim 17 wherein R2 and R3 are individually selected from the group consisting of
Claim 20
Dependent Claim 6 words
Polymers comprising units of the formula
Claim 21
Dependent Claim 6 words
Polymers comprising units of the formula
Claim 22
Dependent Claim 11 words
Polymers consisting essentially of units of the formula of claim 19.
Claim 23
Dependent Claim 11 words
Polymers consisting essentially of units of the formula of claim 1.
Claim 24
Dependent Claim 11 words
Polymers consisting essentially of units of the formula of claim 2.
Claim 25
Dependent Claim 30 words
A process for preparing polyphenylquinoxalines comprising reacting an aromatic tetramine compound containing two sets of ortho-amine functions attached to an aromatic nucleus with a diglyoxal type compound of the formula
Claim 26
Dependent Claim 30 words
A process for preparing polyphenylquinoxalines comprising reacting an aromatic tetramine compound containing two sets of ortho-amine functions attached to an aromatic nucleus with a diglyoxal type compound of the formula
Claim 27
Dependent Claim 26 words
The product produced by exposing a polymer of claim 19 to elevated temperatures whereat said polymer undergoes crosslinking via said -CN, -OCN -CNO, or -C*CH groups.
Claim 28
Dependent Claim 29 words
A process comprising reacting a polyphenylquinoxaline with at least one compound selected from benzil, benzoyl chloride, and o-phenylenediamine whereby there are formed quinoxaline or benzimidazole rings on said polyphenylquinoxaline.
Claim 29
Dependent Claim 29 words
A process comprising reacting a polyphenylquinoxaline with at least one compound selected from benzil, benzoyl chloride, and o-phenylenediamine whereby there are formed quinoxaline or benzimidazole rings on said polyphenylquinoxaline.
Claim 30
Dependent Claim 11 words
Polymers of claim 1 comprising at least five of said units.
Claim 31
Dependent Claim 11 words
Polymers of claim 2 comprising at least five of said units.
Claim 32
Dependent Claim 11 words
Polymers of claim 19 comprising at least five of said units.
Claim 33
Dependent Claim 13 words
Polymers of claim 1 consisting essentially of at least five of said units.
Claim 34
Dependent Claim 13 words
Polymers of claim 2 consisting essentially of at least five of said units.
Claim 35
Dependent Claim 13 words
Polymers of claim 19 consisting essentially of at least five of said units.
Claim 36
Dependent Claim 21 words
Polymers of claim 19 wherein R2 and R3 are each a monovalent aromatic group having a -CN or -OCN group thereon.
Claim 37
Dependent Claim 11 words
Polymers consisting essentially of units of the formula of claim 32.
Claim 38
Dependent Claim 11 words
Polymers of claim 32 comprising at least five of said units.
Claim 39
Dependent Claim 13 words
Polymers of claim 32 consisting essentially of at least five of said units.
Claim 40
Dependent Claim 21 words
The product produced by exposing polymers of claim 1 to elevated temperatures whereat said polymers undergo crosslinking via R4 and R5.

References Cited (Backward Citations)

US2895944A Cited
US3661850A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1977-12-02 1978-06-03 1978-12-03 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1981-12-02 1982-06-03 1982-12-03 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1985-12-02 1986-06-03 1986-12-03 $7700.00 Window Closed / Lapsed

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