US4438273A
Expired / Lapsed
US
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Isoimide containing oligomers
Assignee: Raytheon Co
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Filing: 1981-07-24
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Granted: 1984-03-20
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Expires: 2001-07-24
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. The oligomers of the present invention 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 deletrious gases.
Inventors
- 👤 Abraham L. Landis
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 15:41
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/02; C08G73/06; C08G73/10; C08G73/1089; C07; C07D; C07D307/00; C07D307/77; C07D307/87; C07D307/90
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
104 words
A polymerizable isoimide-containing oligomer prepared by: (a) reacting a carboxylic acid anhydride having the formula: ##STR26## where R is a tetravalent organic group containing 2 to 27 carbon atoms, with a functional amine having the formula: H.sub.2 N--R.sub.1 --X wherein R 1 is a divalent organic group containing 1 to 20 carbon atoms and X is a radical selected from the group consisting of --C.tbd.CH, --CH═CH 2 , --CN, and ##STR27## where R 4 is H or CH 3 ; and (b) dehydrating the product under conditions to form an isoimide-containing oligomer having the formula: ##STR28## where R 1 and X are defined above.
Claim 2
Dependent Claim
104 words
A polymerizable isoimide-containing oligomer prepared by: (a) reacting a carboxylic acid anhydride having the formula: ##STR26## where R is a tetravalent organic group containing 2 to 27 carbon atoms, with a functional amine having the formula: H.sub.2 N--R.sub.1 --X wherein R 1 is a divalent organic group containing 1 to 20 carbon atoms and X is a radical selected from the group consisting of --C.tbd.CH, --CH═CH 2 , --CN, and ##STR27## where R 4 is H or CH 3 ; and (b) dehydrating the product under conditions to form an isoimide-containing oligomer having the formula: ##STR28## where R 1 and X are defined above.
Claim 3
Dependent Claim
66 words
Cis and trans isomers of an oligomer having the formulae: ##STR29## and ##STR30## where 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, and X is a radical selected from the group consisting of --C.tbd.CH, --CH═CH 2 , --CN, and ##STR31## where R 4 is H or CH 3 .
Claim 4
Dependent Claim
66 words
Cis and trans isomers of an oligomer having the formulae: ##STR29## and ##STR30## where 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, and X is a radical selected from the group consisting of --C.tbd.CH, --CH═CH 2 , --CN, and ##STR31## where R 4 is H or CH 3 .
Claim 5
Dependent Claim
60 words
An isoimide oligomer having the formula: ##STR32## where 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, and X is a radical selected from the group consisting of --CH.tbd.CH, --CH═CH 2 , --CN, and ##STR33## where R 4 is H or CH 3 .
Claim 6
Dependent Claim
60 words
An isoimide oligomer having the formula: ##STR32## where 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, and X is a radical selected from the group consisting of --CH.tbd.CH, --CH═CH 2 , --CN, and ##STR33## where R 4 is H or CH 3 .
Claim 7
Dependent Claim
23 words
An oligomer as defined in claim 1 wherein R is selected from the group consisting of aryl containing 6 to 18 carbon atoms.
Claim 8
Dependent Claim
80 words
An oligomer as defined in claim 3 wherein R is selected from the group consisting of: ##STR34## wherein Y is selected from the group consisting of ##STR35## --(CH 2 ) x --, --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: ##STR36## wherein R 2 and R 3 are each selected from the group consisting of aryl and alkyl.
Claim 9
Dependent Claim
109 words
A process for preparing an isoimide-containing oligomer which comprises: (a) reacting a carboxylic acid dianhydride having the formula: ##STR37## wherein R is a tetravelent organic group containing 2 to 27 carbon atoms, with a functional amine having the formula H 2 N--R 1 --X wherein R 1 is a divalent organic group containing 1 to 20 carbon atoms, and (b) dehydrating the product under conditions to form an isoimide-containing oligomer having the formula: ##STR38## where R and R 1 are defined above, and X is a radical selected from the group consisting of --C.tbd.CH, --CH═CH 2 , --CN, and ##STR39## where R 4 is H or CH 3 .
Claim 10
Dependent Claim
109 words
A process for preparing an isoimide-containing oligomer which comprises: (a) reacting a carboxylic acid dianhydride having the formula: ##STR37## wherein R is a tetravelent organic group containing 2 to 27 carbon atoms, with a functional amine having the formula H 2 N--R 1 --X wherein R 1 is a divalent organic group containing 1 to 20 carbon atoms, and (b) dehydrating the product under conditions to form an isoimide-containing oligomer having the formula: ##STR38## where R and R 1 are defined above, and X is a radical selected from the group consisting of --C.tbd.CH, --CH═CH 2 , --CN, and ##STR39## where R 4 is H or CH 3 .
Claim 11
Dependent Claim
14 words
An oligomer as defined in claim 1 wherein the functional amine is 3-aminophenyl acetylene.
Claim 12
Dependent Claim
16 words
An oligiomer as defined in claim 1 wherein the dehydration is effected with a dehydrating agent.
Claim 13
Dependent Claim
14 words
An oligomer as defined in claim 8 wherein the dehydrating agent is trifluoroacetic anhydride.
Claim 14
Dependent Claim
13 words
An oligomer as defined in claim 1 wherein the anhydride is benzophenonetetracarboxylic dianhydride.
Claim 15
Dependent Claim
64 words
An oligomer as defined in claim 1 wherein the anhydride is a dianhydride having the formula: ##STR40## wherein Y is selected from the group consisting of ##STR41## --(CF 2 ) x -- wherein x is an integer from 1 to 5, a group having the formula: ##STR42## wherein R 2 and R 3 are each selected from the group consising of aryl and alkyl.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-03-20 | 1987-09-19 | 1988-03-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-03-20 | 1991-09-19 | 1992-03-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-03-20 | 1995-09-19 | 1996-03-20 | $7700.00 | Window Closed / Lapsed |