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US4537947A
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Chain-extending functional polyimides by dipole reactions
Assignee: University of Notre Dame
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Filing: 1975-03-14
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Granted: 1985-08-27
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Expires: 1995-03-14
Abstract
Abstract Aromatic polyimides with various functional end-groups such as --CH═CH 2 , --C.tbd.CH, --CN and --CHO are chain-extended (molecular weight increased) by reacting the functional groups with aromatic bis-dipoles. A representative bis-dipole is 1,4-benzene-dinitrile oxide. These polyimides can be shaped and formed prior to chain extending. The aromatic polyimides appropriate for chain-extending are formed by the reaction of aromatic dianhydrides, aromatic amines and monoamines which contain the functional groups.
Inventors
- 👤 Gaetano F. D'Alelio
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 23:43
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/1003; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/64; C08G18/6415; C08G18/6438; C08G73/1057; C08G73/1064; C08G73/1067; C08G73/1071; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31678; Y10T428/31681
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
159 words
A polymeric chain-extending process comprising: reacting one mole of a polyimide of the formula: ##STR22## wherein Ar' is a tetravalent aromatic organic radical, the four carbonyl groups being attached directly to separate carbon atoms and each pair of carbonyl groups being attached to adjacent carbon atoms in the Ar' radical, Ar is a divalent aromatic organic radical, R is a hydrocarbon radical of 1 to 12 carbon atoms, and n is a positive integer of at least one, and A is a radical selected from the group consisting of --CH═CHR°, --C.tbd.CR°, --CN, --CHO and --CH═NR" wherein R" is a monovalent aromatic organic radical of 6 to 12 carbon atoms and R° is H or R, with at least 3/4 mole of an aromatic bis-dipole of the formula: Q--Ar--Q wherein Ar is as defined above and Q is selected from the group consisting of ##STR23## wherein R'" is an aliphatic or aromatic organic radical of 1 to 12 carbon atoms.
Claim 2
Dependent Claim
159 words
A polymeric chain-extending process comprising: reacting one mole of a polyimide of the formula: ##STR22## wherein Ar' is a tetravalent aromatic organic radical, the four carbonyl groups being attached directly to separate carbon atoms and each pair of carbonyl groups being attached to adjacent carbon atoms in the Ar' radical, Ar is a divalent aromatic organic radical, R is a hydrocarbon radical of 1 to 12 carbon atoms, and n is a positive integer of at least one, and A is a radical selected from the group consisting of --CH═CHR°, --C.tbd.CR°, --CN, --CHO and --CH═NR" wherein R" is a monovalent aromatic organic radical of 6 to 12 carbon atoms and R° is H or R, with at least 3/4 mole of an aromatic bis-dipole of the formula: Q--Ar--Q wherein Ar is as defined above and Q is selected from the group consisting of ##STR23## wherein R'" is an aliphatic or aromatic organic radical of 1 to 12 carbon atoms.
Claim 3
Dependent Claim
15 words
The process of claim 1 wherein about 1-2 moles of the aromatic bis-dipole are used.
Claim 4
Dependent Claim
21 words
The process of claim 1 wherein the bis-dipole is selected from the group consisting of 1,4-benzene-dinitrile oxide, 1,4-benzenedi(phenylnitrilimine) and 1,4-benzenedi(phenylnitrile ylide).
Claim 5
Dependent Claim
55 words
The process of claim 1 wherein Ar' is selected from the group consisting of ##STR24## and Ar is selected from the group consisting of ##STR25## and multiples thereof connected to each other by R IV , wherein R IV is alkylene of 1 to 3 carbon atoms, ##STR26## --O--, --S--, --CH═CH--, and --SO 2 --.
Claim 6
Dependent Claim
25 words
The process of claim 4 wherein R is selected from the group consisting of --CH 2 -- and ##STR27## and n is 4 to 20.
Claim 7
Dependent Claim
9 words
The process of claim 5 wherein R° is H.
Claim 8
Dependent Claim
148 words
A polymeric chain-extending process comprising: reacting one mole of a polyimide of the formula: ##STR28## wherein Ar' is selected from the group consisting of ##STR29## and Ar is selected from the group consisting of ##STR30## and multiples thereof connected to each other by R IV , wherein R IV is alkylene of 1 to 3 carbon atoms, ##STR31## --O--, --S--, --CH═CH--, and --SO 2 --, R is --CH 2 -- or ##STR32## n is at least 1, and A is a radical selected from the group consisting of --CH═CH 2 , --CH.tbd.CH, --CN, --CHO and --CH═CR" wherein R" is a monovalent aromatic organic radical of 6 to 12 carbon atoms, with at least 3/4 mole of an aromatic bis-dipole of the formula: ##STR33## wherein Q is selected from the group consisting of ##STR34## wherein R'" is an aliphatic or aromatic organic radical of 1 to 12 carbon atoms.
Claim 9
Dependent Claim
148 words
A polymeric chain-extending process comprising: reacting one mole of a polyimide of the formula: ##STR28## wherein Ar' is selected from the group consisting of ##STR29## and Ar is selected from the group consisting of ##STR30## and multiples thereof connected to each other by R IV , wherein R IV is alkylene of 1 to 3 carbon atoms, ##STR31## --O--, --S--, --CH═CH--, and --SO 2 --, R is --CH 2 -- or ##STR32## n is at least 1, and A is a radical selected from the group consisting of --CH═CH 2 , --CH.tbd.CH, --CN, --CHO and --CH═CR" wherein R" is a monovalent aromatic organic radical of 6 to 12 carbon atoms, with at least 3/4 mole of an aromatic bis-dipole of the formula: ##STR33## wherein Q is selected from the group consisting of ##STR34## wherein R'" is an aliphatic or aromatic organic radical of 1 to 12 carbon atoms.
Claim 10
Dependent Claim
11 words
The process of claim 7 wherein n is 4 to 20.
Claim 11
Dependent Claim
15 words
The process of claim 7 wherein about 1-2 moles of the aromatic bis-dipole are used.
Claim 12
Dependent Claim
9 words
The process of claim 7 wherein R'" is ##STR35##
Claim 13
Dependent Claim
24 words
The process of claim 7 wherein n is 4 to 20, about 1-2 moles of the aromatic bis-dipole are used and R'" is ##STR36##
Claim 14
Dependent Claim
16 words
The process of claim 1 wherein the reaction is conducted in a solvent for the reactants.
Claim 15
Dependent Claim
16 words
The process of claim 7 wherein the reaction is conducted in a solvent for the reactants.
Claim 16
Dependent Claim
10 words
A cross-linked polymer prepared by the process of claim 1.
Claim 17
Dependent Claim
10 words
A cross-linked polymer prepared by the process of claim 7.
Claim 18
Dependent Claim
10 words
A cross-linked polymer prepared by the process of claim 11.
Claim 19
Dependent Claim
10 words
A cross-linked polymer prepared by the process of claim 13.
Claim 20
Dependent Claim
11 words
The process of claim 1 wherein n is at least 4.
Claim 21
Dependent Claim
9 words
The process of claim 18 wherein Ar' is ##STR37##
Claim 22
Dependent Claim
83 words
The process of claim 19 wherein Ar is selected from the group consisting of --C 6 H 4 SO 2 C 6 H 4 --, --C 6 H 4 OC 6 H 4 SO 2 C 6 H 4 OC 6 H 4 --, --C 6 H 4 OC 6 H 4 OC 6 H 4 --, --C 6 H 4 OC 6 H 4 --, --C 6 H 4 CH 2 C 6 H 4 -- and --C 6 H 4 --.
Claim 23
Dependent Claim
18 words
The process of claim 18 wherein A is selected from the group consisting of --CH═CH 2 and --C.tbd.CH.
Claim 24
Dependent Claim
18 words
The process of claim 19 wherein A is selected from the group consisting of --CH═CH 2 and --C.tbd.CH.
Claim 25
Dependent Claim
18 words
The process of claim 20 wherein A is selected from the group consisting of --CH═CH 2 and --C.tbd.CH.
Claim 26
Dependent Claim
41 words
The process of claim 18 wherein RA is selected from the group consisting of --C 6 H 4 C.tbd.CH, --CH 2 C.tbd.CH, --C 6 H 4 CH═CH 2 , --CH 2 CH═CH 2 and --CH 2 C 6 H 4 C.tbd.CH.
Claim 27
Dependent Claim
41 words
The process of claim 19 wherein RA is selected from the group consisting of --CH 6 H 4 C.tbd.CH, --CH 2 C.tbd.CH, --C 6 H 4 CH═CH 2 , --CH 2 CH═CH 2 and --CH 2 C 6 H 4 C.tbd.CH.
Claim 28
Dependent Claim
41 words
The process of claim 20 wherein RA is selected from the group consisting of --C 6 H 4 C.tbd.CH, --CH 2 C.tbd.CH, --C 6 H 4 CH═CH 2 , --CH 2 CH═CH 2 and --CH 2 C 6 H 4 C.tbd.CH.
References Cited (Backward Citations)
US3864309A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-08-26 | 1989-02-25 | 1989-08-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-08-26 | 1993-02-25 | 1993-08-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-08-26 | 1997-02-25 | 1997-08-27 | $7700.00 | Window Closed / Lapsed |