US4495342A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Isoimide containing oligomers
Assignee: Raytheon Co
•
Filing: 1983-09-26
•
Granted: 1985-01-22
•
Expires: 2003-09-26
Abstract
Abstract A class of relatively low molecular-weight oligomers containing at least one isoimide group and terminal groups capable of undergoing an addition polymerization reaction are provided. These oligomers are characterized by excellent solubility in common solvents and a melting temperature considerably lower than their cure temperature, thus enabling the oligomers to be formed into cured polymers more slowly and at lower temperatures, all without the evolution of deleterious gases. The oligomers of the present invention may be formed by reacting an aromatic dianhydride with an aromatic diamine, followed by reaction with a monoanhydride. The resulting product is dehydrated to form the isoimide-containing oligomer.
Inventors
- 👤 Abraham L. Landis
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 02:42
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/1089
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
162 words
A polymerizable isoimide-containing oligomer prepared by (a) reacting in a chosen organic solvent a dianhydride having the formula: ##STR38## where R is a tetravalent organic group containing 2 to 27 carbon atoms, with a diamine having the formula: H.sub.2 N--R.sub.5 --NH.sub.2 wherein R 5 is a divalent organic group containing 2 to 30 carbon atoms; (b) reacting the product of (a) with a monoanhydride having the formula: ##STR39## where R 7 is a radical containing an alkenylene group, a heterocyclic group, or a trivalent aryl group having an x radical substituted thereon wherein x is selected from the group consisting of ##STR40## wherein R 4 is H or --CH 3 , and CN (c) cooling the reaction mixture produced in (b) to a selected temperature about at least as low as ambient temperature, and (d) adding to said reaction mixture at said selected temperature a chosen dehydrating agent to dehydrate and cyclize the product of (b) to thereby form said isoimide-containing oligomer.
Claim 2
Dependent Claim
162 words
A polymerizable isoimide-containing oligomer prepared by (a) reacting in a chosen organic solvent a dianhydride having the formula: ##STR38## where R is a tetravalent organic group containing 2 to 27 carbon atoms, with a diamine having the formula: H.sub.2 N--R.sub.5 --NH.sub.2 wherein R 5 is a divalent organic group containing 2 to 30 carbon atoms; (b) reacting the product of (a) with a monoanhydride having the formula: ##STR39## where R 7 is a radical containing an alkenylene group, a heterocyclic group, or a trivalent aryl group having an x radical substituted thereon wherein x is selected from the group consisting of ##STR40## wherein R 4 is H or --CH 3 , and CN (c) cooling the reaction mixture produced in (b) to a selected temperature about at least as low as ambient temperature, and (d) adding to said reaction mixture at said selected temperature a chosen dehydrating agent to dehydrate and cyclize the product of (b) to thereby form said isoimide-containing oligomer.
Claim 3
Dependent Claim
30 words
An oligomer as defined in claim 1, wherein R 5 is an arylene group containing 6 to 30 carbon atoms or a heterocyclic group containing 5 to 18 carbon atoms.
Claim 4
Dependent Claim
19 words
An oligomer as defined in claim 1, wherein R is an aryl group containing 6 to 18 carbon atoms.
Claim 5
Dependent Claim
85 words
An oligomer as defined in claim 1, wherein R is selected from the group consisting of: ##STR41## wherein Y is selected from the group consisting of: ##STR42## --(CH 2 ) x , --C(CH 3 ) 2 --, --O--, --S--, --SO 2 --, --C(CF 3 ) 2 --, --(CF 2 ) x -- wherein x is an integer from 1 to 5, and a group having the formula: ##STR43## wherein R 2 and R 3 are each selected from the group consisting of aryl and alkyl.
Claim 6
Dependent Claim
13 words
An oligomer as defined in claim 1 wherein the dehydrating agent is N,N-dicyclohexylcarbodiimide.
Claim 7
Dependent Claim
13 words
An oligomer as defined in claim 1 wherein the dianhydride is benzophenonetetracarboxylic dianhydride.
Claim 8
Dependent Claim
12 words
An oligomer as defined in claim 1, wherein the diamine is 1,3-di(3-aminophenoxy)benzene.
Claim 9
Dependent Claim
12 words
An oligomer as defined in claim 1 wherein the diamine is 4,4'-oxydianiline.
Claim 10
Dependent Claim
85 words
An oligomer as defined in claim 1 wherein the diamine is a compound having the formula: ##STR44## wherein Y is selected from the group consisting of ##STR45## --(CH 2 ) x , --C(CH 3 ) 2 --, --O--, --S--, --SO 2 --, --C(CF 3 ) 2 --, --(CF 2 ) x -- wherein x is an integer from 1 to 5, and a group having the formula: ##STR46## wherein R 2 and R 3 are each defined from the group consisting of aryl and alkyl.
Claim 11
Dependent Claim
82 words
An oligomer as defined in claim 1, wherein the dianhydride has the formula: ##STR47## wherein Y is selected from the group consisting of ##STR48## --(CH 2 ) x , --C(CH 3 ) 2 --, --O--, --S--, --SO 2 --, --C(CF 3 ) 2 --, --(CF 2 ) x -- wherein x is an integer from 1 to 5, and a group having the formula: ##STR49## wherein R 2 and R 3 are each selected from the group consisting of aryl and alkyl.
Claim 12
Dependent Claim
82 words
An oligomer as defined in claim 2, wherein the dianhydride has the formula: ##STR50## wherein Y is selected form the group consisting of ##STR51## --(CH 2 ) x , --C(CH 3 ) 2 --, --O--, --S--, --SO 2 --, --C(CF 3 ) 2 --, --(CF 2 ) x -- wherein x is an integer from 1 to 5, and a group having the formula: ##STR52## wherein R 2 and R 3 are each selected from the group consisting of aryl and alkyl.
Claim 13
Dependent Claim
85 words
An oligomer as defined in claim 11 wherein the diamine is a compound having the formula: ##STR53## wherein Y is selected from the group consisting of ##STR54## --(CH 2 ) x , --C(CH 3 ) 2 --, --O--, --S--, --SO 2 --, --C(CF 3 ) 2 --, --(CF 2 ) x -- wherein x is an integer from 1 to 5, and a group having the formula: ##STR55## wherein R 6 and R 12 are each selected from the group consisting of aryl and alkyl.
Claim 14
Dependent Claim
13 words
An oligomer as defined in claim 1 wherein the monoanhydride is maleic anhydride.
Claim 15
Dependent Claim
41 words
An oligomer as defined in claim 1 wherein the monoanhydride has the formula: ##STR56## wherein R 8 , R 9 and R 10 are the same or different and are each selected from the group consisting of H or lower alkyl.
Claim 16
Dependent Claim
92 words
An isoimide oligomer having the formula: ##STR57## wherein R is a tetravalent organic group containing 2 to 27 carbon atoms, R 5 is a divalent organic group containing from 2 to 30 carbon atoms, R 7 is a radical containing an alkylene group, a heterocyclic group, or a trivalent aryl group having an x radical substituted thereon wherein x is selected from the the group consisting of ##STR58## wherein R 4 is H or --CH 3 , and CN, and m denotes the degree of polymerization and is 1 to about 30.
Claim 17
Dependent Claim
92 words
An isoimide oligomer having the formula: ##STR57## wherein R is a tetravalent organic group containing 2 to 27 carbon atoms, R 5 is a divalent organic group containing from 2 to 30 carbon atoms, R 7 is a radical containing an alkylene group, a heterocyclic group, or a trivalent aryl group having an x radical substituted thereon wherein x is selected from the the group consisting of ##STR58## wherein R 4 is H or --CH 3 , and CN, and m denotes the degree of polymerization and is 1 to about 30.
Claim 18
Dependent Claim
20 words
An oligomer as defined in claim 15 wherein R 5 is an arylene group containing 6 to 18 carbon atoms.
Claim 19
Dependent Claim
19 words
An oligomer as defined in claim 15 wherein R is an aryl group containing 6 to 18 carbon atoms.
Claim 20
Dependent Claim
85 words
An oligomer as defined in claim 15, wherein R is selected from the group consisting of: ##STR59## wherein Y is selected from the group consisting of ##STR60## --(CH 2 ) x , --C(CH 3 ) 2 --, --O--, --S--, --SO 2 --, --C(CF 3 ) 2 --, --(CF 2 ) x -- wherein x is an integer from 1 to 5, and a group having the formula: ##STR61## wherein R 2 and R 3 are each selected from the group consisting of aryl and alkyl.
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) | 1988-01-22 | 1988-07-23 | 1989-01-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-01-22 | 1992-07-23 | 1993-01-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-01-22 | 1996-07-23 | 1997-01-22 | $7700.00 | Window Closed / Lapsed |