US4316845A
Expired / Lapsed
US
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Polyimide derivatives having terminal acetylenic groups
Assignee: Plastics Engineering Co
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Filing: 1980-01-25
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Granted: 1982-02-23
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Expires: 2000-01-25
Abstract
Abstract Novel compositions comprising acetylenic polyimide-polyamides and processes for their preparation are disclosed herein. These new compositions are primarily derivatives of anhydride-terminated aromatic polyimides from which they are prepared by amidation to provide acetylenic amide groups having terminal --C═CH groups. These new compositions are more tractable than the original anhydride-terminated polyimides and can be converted at appropriate lower temperatures to crosslinked, insoluble, infusible polymers without by-product formation thereby extending greatly the applications for which the aromatic polyimides can be employed. Also included are monomeric compounds containing acetylenic amide groups derived from monomeric tetracarboxylic dianhydrides. These are particularly useful as crosslinking agents.
Inventors
- 👤 Gaetano F. D'Alelio
- 👤 Phillip A. Waitkus
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 01:42
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/14
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
174 words
A polyimide-amide having terminal acetylenic amide groups and having the formula: ##STR76## wherein: Ar' is a tetravalent aromatic benzenoid 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 except that in the case of the Ar' being a naphthalene radical one or both pairs of the carbonyl groups may be attached to peri carbon atoms; Ar is a divalent aromatic benzenoid radical; n is an integer of at least one; Y is NRR' R is an organic moiety containing 1 to 20 carbon atoms; said organic moiety consisting of a hydrocarbon radical or two or three hydrocarbon radicals joined by a --O--, --SO 2 -- or --COO-- group R' is an organic moiety containing 2 to 14 carbon atoms and having a terminal CH.tbd.C-- structure, said organic moiety consisting of a hydrocarbon radical or two or three hydrocarbon radicals joined by a --O--, --SO 2 -- or --COO-- group; and Y' is NRR or --OR.
Claim 2
Dependent Claim
174 words
A polyimide-amide having terminal acetylenic amide groups and having the formula: ##STR76## wherein: Ar' is a tetravalent aromatic benzenoid 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 except that in the case of the Ar' being a naphthalene radical one or both pairs of the carbonyl groups may be attached to peri carbon atoms; Ar is a divalent aromatic benzenoid radical; n is an integer of at least one; Y is NRR' R is an organic moiety containing 1 to 20 carbon atoms; said organic moiety consisting of a hydrocarbon radical or two or three hydrocarbon radicals joined by a --O--, --SO 2 -- or --COO-- group R' is an organic moiety containing 2 to 14 carbon atoms and having a terminal CH.tbd.C-- structure, said organic moiety consisting of a hydrocarbon radical or two or three hydrocarbon radicals joined by a --O--, --SO 2 -- or --COO-- group; and Y' is NRR or --OR.
Claim 3
Dependent Claim
9 words
The polyimide-amide of claim 1 of the formula: ##STR77##
Claim 4
Dependent Claim
12 words
The polyimide-amide of claim 2 in which R is CH 3 .
Claim 5
Dependent Claim
10 words
The polyimide-amide of claim 1 in which Y' is NRR.
Claim 6
Dependent Claim
10 words
The polyimide-amide of claim 1 in which Y' is OR.
Claim 7
Dependent Claim
10 words
The polyimide-amide of claim 1 in which Y is --OR'.
Claim 8
Dependent Claim
12 words
The polyimide-amide of claim 1 in which R' is --CH 2 C.tbd.CH.
Claim 9
Dependent Claim
10 words
The polyimide-amide of claim 1 in which R is R'.
Claim 10
Dependent Claim
10 words
The polyimide-diamide of claim 2 in which R is R'.
Claim 11
Dependent Claim
12 words
The polyimide-diamide of claim 3 in which R' is --CH 2 C.tbd.CH.
Claim 12
Dependent Claim
9 words
The polyimide-amide of claim 1 in which the ##STR78##
Claim 13
Dependent Claim
49 words
is the residue of a diamine selected from the class consisting of: 1. 3-and 1,4-(NH 2 ) 2 benzene; 2,3-; 2,5-; 2,6- and 3,5-(NH 2 ) 2 toluene; 3,3'-; 4,4'- and 3,4'-methylene dianiline; 4,4'-; 3,3'- and 3,4'-oxydianiline; 4,4'-; 3,3'- and 3,4'-sulfonyldianiline; 1,3-; 1,4- and 1,2-bis(3-aminophenoxy)benzene; and 1,3- and 1,4-bis(4-aminophenoxy)benzene.
Claim 14
Dependent Claim
49 words
is the residue of a diamine selected from the class consisting of: 1. 3-and 1,4-(NH 2 ) 2 benzene; 2,3-; 2,5-; 2,6- and 3,5-(NH 2 ) 2 toluene; 3,3'-; 4,4'- and 3,4'-methylene dianiline; 4,4'-; 3,3'- and 3,4'-oxydianiline; 4,4'-; 3,3'- and 3,4'-sulfonyldianiline; 1,3-; 1,4- and 1,2-bis(3-aminophenoxy)benzene; and 1,3- and 1,4-bis(4-aminophenoxy)benzene.
Claim 15
Dependent Claim
13 words
The polyimide-amide of claim 11 in which the diamine is a methylene dianiline.
Claim 16
Dependent Claim
12 words
The polyimide-amide of claim 1 in which n is at least two.
Claim 17
Dependent Claim
18 words
The polyimide-amide of claim 1 in which Ar' is a radical selected from the class consisting of: ##STR79##
Claim 18
Dependent Claim
10 words
The polyimide-amide of claim 1 in which Ar' is: ##STR80##
Claim 19
Dependent Claim
13 words
The polyimide-amide of claim 11 in which the diamine is a sulfonyl dianiline.
Claim 20
Dependent Claim
12 words
The polyimide-amide of claim 11 in which the diamine is an oxydianiline.
Claim 21
Dependent Claim
12 words
The polyimide-amide of claim 11 in which the diamine is 2,5-toluene diamine.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-02-22 | 1985-08-24 | 1986-02-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-02-22 | 1989-08-24 | 1990-02-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-02-22 | 1993-08-24 | 1994-02-23 | $7700.00 | Window Closed / Lapsed |