US4197393A
Expired / Lapsed
US
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Biphenylene polymers and resins and the production thereof
Assignee: University Patents Inc
•
Filing: 1978-05-30
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Granted: 1980-04-08
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Expires: 1998-05-30
Abstract
Abstract Polymers of the following formulas, and cross-linked resins formed therefrom through thermal cleavage of the four-membered rings of the biphenylene nuclei, are useful as molding and laminating materials: ##STR1## wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 are the same or different bivalent aromatic hydrocarbon radicals containing six to ten carbons, n is an integer from 100 to 200, m is an integer from 5 to 25, x is an integer from 50 to 100, and y is an integer from 3 to 12. In the preferred modifications, n is an integer from 50 to 190 and m is an integer from 8 to 15, and the preferred ratio of n to m is from about 18:1 to about 20:1; in one species n is about 152 and m is about 8, while in a related species n is about 190 and m is about 10. In the other preferred modifications, x is an integer from 55 to 75 and y is an integer from 6 to 9, and the preferred ratio of x to y is from about 8:1 to about 10:1; in one species x is about 60 and y is about 7, while in a related species x is about 72 and y is about 8.
Inventors
- 👤 Raymond J. Swedo
- 👤 Carl S. Marvel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 11:53
CPC Classifications
C; C08; C08G; C08G63/00; C08G63/68; C08G63/688; C08G63/6884; C08G63/6886; C07; C07C; C07C63/00; C07C63/33; C07C63/49
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
76 words
A linear polymer biphenylene polymer consisting essentially of one of the general formulae ##STR2## wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 are the same or different bivalent aromatic hydrocarbon radicals containing six to ten carbons, n is an integer from 100 to 200, m is an integer from 5 to 25, x is an integer from 50 to 100, and y is an integer from 3 to 12.
Claim 2
Dependent Claim
76 words
A linear polymer biphenylene polymer consisting essentially of one of the general formulae ##STR2## wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 are the same or different bivalent aromatic hydrocarbon radicals containing six to ten carbons, n is an integer from 100 to 200, m is an integer from 5 to 25, x is an integer from 50 to 100, and y is an integer from 3 to 12.
Claim 3
Dependent Claim
56 words
A polymer according to claim 1 of the formula ##STR3## wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 are the same or different bivalent aromatic hydrocarbon radicals containing six to ten carbons, n is a integer from 100 to 200 and m is an integer from 5 to 25.
Claim 4
Dependent Claim
25 words
A polymer according to claim 2 wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 contain six carbon atoms.
Claim 5
Dependent Claim
24 words
A polymer according to claim 3 wherein n is an integer from 150 to 190 and m is an integer from 8 to 15.
Claim 6
Dependent Claim
18 words
A polymer according to claim 4 wherein the ratio of n to m is about 18:l to 20:1.
Claim 7
Dependent Claim
16 words
A polymer according to claim 5 wherein n is about 152 and m is about 8.
Claim 8
Dependent Claim
16 words
A polymer according to claim 6 wherein n is about 190 and m is about 10.
Claim 9
Dependent Claim
58 words
A polymer according to claim 1 of the formula ##STR4## wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 , and Ar 5 are the same or different bivalent aromatic hydrocarbon radicals containing six to ten carbon atoms, x is an integer from 50 to 100, and y is an integer from 3 to 12.
Claim 10
Dependent Claim
26 words
A polymer according to claim 8 wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 , and Ar 5 contain six carbon atoms.
Claim 11
Dependent Claim
24 words
A polymer according to claim 9 wherein x is an integer from 55 to 75 and y is an integer from 6 to 9.
Claim 12
Dependent Claim
18 words
A polymer according to claim 10 wherein the ratio of x to y is about 8:1 to 10:1.
Claim 13
Dependent Claim
16 words
A polymer according to claim 11 wherein x is about 60 and y is about 7.
Claim 14
Dependent Claim
16 words
A polymer according to claim 12 wherein x is about 72 and y is about 8.
Claim 15
Dependent Claim
97 words
Method of producing a polymer as defined by claim 2 where comprises: (a) reacting a diaryl ether of the formula Ar.sub.1 --O--Ar.sub.2 wherein Ar 1 and Ar 2 are the same or different bivalent aromatic hydrocarbon radicals containing six to ten carbon atoms, with a mixture of acid halides of the formulas X--CO--AR.sub.3 --CO--X and ##STR5## wherein X is chlorine or bromine and Ar 3 is a bivalent aromatic hydrocarbon radical containing six to ten carbon atoms, in an inert organic solvent containing anhydrous aluminum chloride, and (b) removing the polymer so formed from the reaction mixture.
Claim 16
Dependent Claim
21 words
Method of claim 14 wherein Ar 1 , Ar 2 and Ar 3 contain six carbon atoms and X is chlorine.
Claim 17
Dependent Claim
12 words
Method of claim 15 wherein the organic solvent is a halogenated alkane.
Claim 18
Dependent Claim
10 words
Method of claim 16 wherein the organic solvent is dichloroethane.
Claim 19
Dependent Claim
109 words
Method of producing a polymer as defined by claim 8 which comprises: (a) reacting a diaryl ether of the formula Ar.sub.1 --O--Ar.sub.2 --SO.sub.2 --Ar.sub.3 --O--Ar.sub.4 --SO.sub.2 --Ar.sub.2 --O--Ar.sub.1 wherein Ar 1 , Ar 2 , Ar 3 and Ar 4 are the same or different bivalent aromatic hydrocarbon radicals containing six to ten carbon atoms, with a mixture of acid halides of the formulas X--CO--Ar.sub.5 --CO--X and ##STR6## wherein X is chlorine or bromine and AR 5 is a bivalent aromatic hydrocarbon radical containing six to ten carbon atoms, in an inert organic solvent containing anhydrous aluminum chloride, and (b) removing the polymer so formed from the reaction mixture.
Claim 20
Dependent Claim
21 words
Method of claim 18 wherein Ar 1 , Ar 2 and Ar 3 contain six carbon atoms and X is chlorine.
Claim 21
Dependent Claim
12 words
Method of claim 19 wherein the organic solvent is a halogenated alkane.
Claim 22
Dependent Claim
10 words
Method of claim 20 wherein the organic solvent is dichloroethane.
Claim 23
Dependent Claim
24 words
Method of crosslinking a polymer defined by claim 1 which comprises heating said polymer at a temperature above the melting point of said polymers.
Claim 24
Dependent Claim
20 words
Method of claim 22 wherein the polymer is heated to a temperature in the range from 300° to 350° C.
Claim 25
Dependent Claim
23 words
A crosslinked resin produced by heating a polymer as defined by claim 1 to a temperature above the melting point of said polymer.
Claim 26
Dependent Claim
25 words
A crosslinked resin as set forth in claim 24 produced by heating the polymer to a temperature in the range from 300° to 350° C.
References Cited (Backward Citations)
US3725070A
Cited
US3859254A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-04-08 | 1983-10-08 | 1984-04-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-04-08 | 1987-10-08 | 1988-04-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-04-08 | 1991-10-08 | 1992-04-08 | $7700.00 | Window Closed / Lapsed |