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US4485231A
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Isoimide containing oligomers
Assignee: Raytheon Co
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Filing: 1983-09-26
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Granted: 1984-11-27
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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 functional mono-amine. The resulting product is then dehydrated to form the isoimide-containing oligomer.
Inventors
- 👤 Abraham L. Landis
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 07:27
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/1089
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
157 words
A polymerizable isoimide-containing oligomer prepared by: (a) reacting in a chosen organic solvent a carboxylic dianhydride having the formula: ##STR38## wherein 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 containg 6 to 30 carbon atoms, (b) reacting the product of (a) with a functional amine having the formula: H.sub.2 N--R.sub.1 --X wherein R 1 is a divalent organic group containg 1 to 20 carbon atoms, and X is a radical having an unsaturated functional group capable of undergoing addition polymerization with another radical having an unsaturated functional group, (c) cooling the reaction mixture produced in (b) to a selected temperature about at least as low as ambient temperature, (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
157 words
A polymerizable isoimide-containing oligomer prepared by: (a) reacting in a chosen organic solvent a carboxylic dianhydride having the formula: ##STR38## wherein 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 containg 6 to 30 carbon atoms, (b) reacting the product of (a) with a functional amine having the formula: H.sub.2 N--R.sub.1 --X wherein R 1 is a divalent organic group containg 1 to 20 carbon atoms, and X is a radical having an unsaturated functional group capable of undergoing addition polymerization with another radical having an unsaturated functional group, (c) cooling the reaction mixture produced in (b) to a selected temperature about at least as low as ambient temperature, (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 X is selected from the group consisting of the formula: ##STR39## wherein R 4 is H or --CH 3 , and --CN.
Claim 4
Dependent Claim
39 words
An oligomer as defined in claim 1, wherein R 5 is selected from the group consisting of heterocyclic containing 6 to 18 carbon atoms, alkylene containing 1 to 5 carbon atoms, and arylene containing 6 to 30 carbon atoms.
Claim 5
Dependent Claim
30 words
An oligomer as defined in claim 1, wherein R is selected from the group consisting of heterocyclic containing 5 to 18 carbons, and aryl containing 6 to 18 carbon atoms.
Claim 6
Dependent Claim
60 words
An oligomer as defined in claim 1, wherein R is selected from the group consisting of: ##STR40## wherein Y is selected from the group consisting of ##STR41## wherein x is an integer from 1 to 5, and a group having the formula: ##STR42## wherein R 2 and R 3 are each selected from the group consisting of aryl and alkyl.
Claim 7
Dependent Claim
14 words
An oligomer as defined in claim 1 wherein the dehydrating agent is trifluoroacetic anhydride.
Claim 8
Dependent Claim
13 words
An oligomer as defined in claim 1 wherein the dianhydride is benzophenonetetracarboxylic dianhydride.
Claim 9
Dependent Claim
12 words
An oligomer as defined in claim 1 wherein the diamine is 1,3-di(3-aminophenoxy)benzene.
Claim 10
Dependent Claim
12 words
An oligomer as defined in claim 1 wherein the diamine is 4,4'-oxydianiline.
Claim 11
Dependent Claim
59 words
An oligomer as defined in claim 1 wherein the diamine is a compound having the formula: ##STR43## wherein Y is selected from the group consisting of ##STR44## wherein x is an integer from 1 to 5, a group having the formula: ##STR45## wherein R 2 and R 3 are each selected from the group consisting of aryl and alkyl.
Claim 12
Dependent Claim
56 words
An oligomer as defined in claim 1, wherein the dianhydride has the formula: ##STR46## wherein Y is selected from the group consisting of ##STR47## wherein x is an integer from 1 to 5, a group having the formula: ##STR48## wherein R 2 and R 3 are each selected from the group consisting of aryl and alkyl.
Claim 13
Dependent Claim
56 words
An oligomer as defined in claim 3 wherein the dianhydride has the formula: ##STR49## wherein Y is selected from the group consisting of ##STR50## wherein x is an integer from 1 to 5, a group having the formula: ##STR51## wherein R 2 and R 3 are each selected from the group consisting of aryl and alkyl.
Claim 14
Dependent Claim
59 words
An oligomer as defined in claim 12 wherein the diamine is a compound having the formula: ##STR52## wherein Y is selected from the group consisting of ##STR53## wherein x is an integer from 1 to 5, a group having the formula: ##STR54## wherein R 6 and R 12 are each selected from the group consisting of aryl and alkyl.
Claim 15
Dependent Claim
19 words
The oligomer of claim 1 wherein R 5 is a divalent aryl group containing 6 to 30 carbon atoms.
Claim 16
Dependent Claim
12 words
The oligomer of claim 1 wherein the functional amine is 3-aminophenyl acetylene.
Claim 17
Dependent Claim
11 words
The oligomer of claim 1 wherein the dehydrating agent is N,N'-dicyclohexylcarbodiimide.
Claim 18
Dependent Claim
13 words
An oligomer as defined in claim 1 wherein the diamine is 2,2-bis[4-(4-aminophenoxy)phenyl] hexafluoropropane.
Claim 19
Dependent Claim
103 words
An isoimide oligomer having the formula: ##STR55## wherein R is a tetravalent organic group containing 2 to 27 carbon atoms, R 1 is a divalent organic group containing 1 to 20 carbon atoms, R 5 is a member selected from the group consisting of a divalent aromatic group containing from 6 to 30 carbon atoms and a heterocyclic group containing from 5 to 18 carbon atoms, X is a radical having an unsaturated functional group capable of undergoing addition polymerization with another radical having an unsaturated functional group, and n denotes the degree of polymerization and is 0 or 1 to about 30.
Claim 20
Dependent Claim
103 words
An isoimide oligomer having the formula: ##STR55## wherein R is a tetravalent organic group containing 2 to 27 carbon atoms, R 1 is a divalent organic group containing 1 to 20 carbon atoms, R 5 is a member selected from the group consisting of a divalent aromatic group containing from 6 to 30 carbon atoms and a heterocyclic group containing from 5 to 18 carbon atoms, X is a radical having an unsaturated functional group capable of undergoing addition polymerization with another radical having an unsaturated functional group, and n denotes the degree of polymerization and is 0 or 1 to about 30.
Claim 21
Dependent Claim
30 words
An oligomer as defined in claim 18, wherein X is selected from the group consisting of the formula: ##STR56## wherein R 4 is H or --CH 3 , and --CN.
Claim 22
Dependent Claim
39 words
An oligomer as defined in claim 18, wherein R 5 is selected from the group consisting of alkylene containing 1 to 5 carbon atoms, heterocyclic containing 5 to 18 carbon atoms, and arylene containing 6 to 30 carbon atoms.
Claim 23
Dependent Claim
23 words
An oligomer as defined in claim 18, wherein R is selected from the group consisting of aryl containing 6 to 18 carbon atoms.
Claim 24
Dependent Claim
59 words
An oligomer as defined in claim 19, wherein R is selected from the group consisting of: ##STR57## wherein Y is selected from the group consisting of ##STR58## wherein x is an integer from 1 to 5, a group having the formula: ##STR59## 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) | 1987-11-27 | 1988-05-28 | 1988-11-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-11-27 | 1992-05-28 | 1992-11-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-11-27 | 1996-05-28 | 1996-11-27 | $7700.00 | Window Closed / Lapsed |