US4316844A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Polyimide derivatives having unsaturated terminal amic acid groups
Assignee: Plastics Engineering Co
•
Filing: 1980-01-25
•
Granted: 1982-02-23
•
Expires: 2000-01-25
Abstract
Abstract Novel compositions comprising unsaturated polyhemi-amic acid compositions 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 unsaturated amide groups having terminal --CH═CH 2 groups as hemi-amic acid groups or their derivatives. 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 unsaturated amide groups derived from monomeric tetracarboxylic dianhydrides. These are particularly useful as crosslinking agents.
Inventors
- 👤 Phillip A. Waitkus
- 👤 Gaetano F. D'Alelio
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 22:51
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: 20
Claim 1
Independent Claim
168 words
A hemi-acid compound of the formula: ##STR70## 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 integer of at least one; R' is an organic moiety containing 2 to 14 carbon atoms and having a terminal --CH═CH 2 structure; said organic moiety consisting of a hydrocarbon radical or two or three hydrocarbon radicals joined by --O--, --SO 2 -- or --COO-- groups R is an organic moiety containing one to 20 carbon atoms; said organic moiety consisting of a hydrocarbon radical or two or three hydrocarbon radicals joined by --O--, --SO 2 --, or --COO-- groups Y" is --OH or X; and X is a halogen.
Claim 2
Dependent Claim
168 words
A hemi-acid compound of the formula: ##STR70## 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 integer of at least one; R' is an organic moiety containing 2 to 14 carbon atoms and having a terminal --CH═CH 2 structure; said organic moiety consisting of a hydrocarbon radical or two or three hydrocarbon radicals joined by --O--, --SO 2 -- or --COO-- groups R is an organic moiety containing one to 20 carbon atoms; said organic moiety consisting of a hydrocarbon radical or two or three hydrocarbon radicals joined by --O--, --SO 2 --, or --COO-- groups Y" is --OH or X; and X is a halogen.
Claim 3
Dependent Claim
12 words
The hemi-amic acid compound of claim 1 in which Y" is OH.
Claim 4
Dependent Claim
12 words
The hemi-amic acid compound of claim 1 in which Y" is X.
Claim 5
Dependent Claim
12 words
The hemi-amic acid compound of claim 3 in which X is chlorine.
Claim 6
Dependent Claim
12 words
The hemi-amic acid compound of claim 4 in which R is R'.
Claim 7
Dependent Claim
15 words
The hemi-amic acid of claim 3 in which R' is --CH 2 CH═CH 2 .
Claim 8
Dependent Claim
15 words
The hemi-amic acid of claim 4 in which R' is --CH 2 CH═CH 2 .
Claim 9
Dependent Claim
13 words
The hemi-amic acid of claim 3 in which R is --CH 3 .
Claim 10
Dependent Claim
13 words
The hemi-amic acid of claim 4 in which R is --CH 3 .
Claim 11
Dependent Claim
21 words
The hemi-amic acid of claim 4 in which R is --CH 2 C 6 H 4 CH 2 CH═CH 2 .
Claim 12
Dependent Claim
20 words
The hemi-amic acid compound of claim 4 in which R is --CH 2 C 6 H 4 CH═CH 2 .
Claim 13
Dependent Claim
18 words
The hemi-amic acid compound of claim 5 in which R and R' are --CH 2 CH═CH 2 .
Claim 14
Dependent Claim
20 words
The hemi-amic acid compound of claim 1 in which Ar' is a radical selected from the class consisting of: ##STR71##
Claim 15
Dependent Claim
12 words
The hemi-amic acid compound of claim 1 in which Ar' is: ##STR72##
Claim 16
Dependent Claim
66 words
The hemi-amic acid compound of claim 1 in which n is at least one and the >N-Ar-N< is the residue of a diamine is 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)benzyene; and 1,3- and 1,4-bis(4-aminophenoxy)benzene
Claim 17
Dependent Claim
15 words
The hemi-amic acid compound of claim 15 in which the diamine is a methylene dianiline.
Claim 18
Dependent Claim
15 words
The hemi-amic acid compound of claim 15 in which the diamine is a sulfonyl dianiline.
Claim 19
Dependent Claim
14 words
The hemi-amic acid compound of claim 15 in which the diamine is a oxydianiline.
Claim 20
Dependent Claim
14 words
The hemi-amic acid compound of claim 15 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 |