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US4180649A
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Homopolymerizable acetylene-terminated tetraimines and process for making same
Assignee: Raytheon Co
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Filing: 1978-11-20
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Granted: 1979-12-25
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Expires: 1998-11-20
Abstract
Abstract Acetylene-substituted tetraimines are synthesized to form oligomers or prepolymers having melting points as low as 40° C. and which can be polymerized into thermoset plastics at temperatures as low as 150° C.
Inventors
- 👤 Norman Bilow
- 👤 William B. Austin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 05:25
CPC Classifications
C; C08; C08F; C08F138/00
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
174 words
A homopolymerizable acetylene substituted tetraimine oligomer having the structure: HC.tbd.C--Ar--N=CH--Ar'--CH═N--R--N═CH--Ar'--CH═N--Ar--C.tbd.CH where: R is a moiety whose structure is selected from the group consisting of ##STR5## wherein; n may range from 0 to about 4, X may be O, S, SO 2 , CH 2 , CF 2 , C 3 F 6 , C 2 F 4 , --CH═CH--, --CH 2 --CH 2 -- a bond or NH and Y may be --CH 3 , --C 2 H 5 , --C 6 H 5 , --CF 3 or Cl; Ar is a moiety selected from the group consisting of ##STR6## wherein n' may range from 0 to 2, X' may be O, S, SO 2 , CF 2 , C 2 F 4 , C 3 F 6 , C 10 H 6 or --C 6 H 4 --C 6 H 4 -- and Y' may be aryl, alkyl, arylakyl, alkylaryl or halogen substituted analogues; and where Ar' may be the same as, but need not be identical to, Ar within the same molecule.
Claim 2
Dependent Claim
174 words
A homopolymerizable acetylene substituted tetraimine oligomer having the structure: HC.tbd.C--Ar--N=CH--Ar'--CH═N--R--N═CH--Ar'--CH═N--Ar--C.tbd.CH where: R is a moiety whose structure is selected from the group consisting of ##STR5## wherein; n may range from 0 to about 4, X may be O, S, SO 2 , CH 2 , CF 2 , C 3 F 6 , C 2 F 4 , --CH═CH--, --CH 2 --CH 2 -- a bond or NH and Y may be --CH 3 , --C 2 H 5 , --C 6 H 5 , --CF 3 or Cl; Ar is a moiety selected from the group consisting of ##STR6## wherein n' may range from 0 to 2, X' may be O, S, SO 2 , CF 2 , C 2 F 4 , C 3 F 6 , C 10 H 6 or --C 6 H 4 --C 6 H 4 -- and Y' may be aryl, alkyl, arylakyl, alkylaryl or halogen substituted analogues; and where Ar' may be the same as, but need not be identical to, Ar within the same molecule.
Claim 3
Dependent Claim
10 words
The tetraimine oligomer of claim 1 wherein R is phenylene.
Claim 4
Dependent Claim
9 words
The oligomer of claim 2 wherein Ar is phenylene.
Claim 5
Dependent Claim
21 words
The oligomer of claim 1 wherein R is --C 6 H 4 --O--C 6 H 4 --O--C 6 H 4 --.
Claim 6
Dependent Claim
9 words
The oligomer of claim 1 wherein Ar is phenylene.
Claim 7
Dependent Claim
9 words
The oligomer of claim 1 wherein Ar' is phenylene.
Claim 8
Dependent Claim
10 words
The oligomer of claim 1 wherein R is phenylene oxyphenylene.
Claim 9
Dependent Claim
25 words
The oligomer of claim 3 wherein said HC.tbd.C-terminal groups are joined to said Ar groups at a meta position with respect to said imine groups.
Claim 10
Dependent Claim
10 words
The tetraimine oligomer of claim 8 wherein R is phenylene.
Claim 11
Dependent Claim
21 words
The oligomer of claim 8 wherein R is --C 6 H 4 --O--C 6 H 4 --O--C 6 H 4 --.
Claim 12
Dependent Claim
9 words
The oligomer of claim 8 wherein Ar is phenylene.
Claim 13
Dependent Claim
9 words
The oligomer of claim 8 wherein Ar' is phenylene.
Claim 14
Dependent Claim
10 words
The oligomer of claim 8 wherein R is phenylene oxyphenylene.
Claim 15
Dependent Claim
41 words
A process for preparing a homopolymerizable acetylene terminated tetraimine oligomer comprising the steps of first reacting aryldicarboxaldehydes with an aryldiamine to form a dicarboxaldehyde terminated diamine and subsequently reacting said dicarboxaldehyde terminated diamine with aminoarylacetylenes thereby forming said acetylene terminated tetraimine.
Claim 16
Dependent Claim
41 words
A process for preparing a homopolymerizable acetylene terminated tetraimine oligomer comprising the steps of first reacting aryldicarboxaldehydes with an aryldiamine to form a dicarboxaldehyde terminated diamine and subsequently reacting said dicarboxaldehyde terminated diamine with aminoarylacetylenes thereby forming said acetylene terminated tetraimine.
Claim 17
Dependent Claim
19 words
The process of claim 14 wherein stiochiometric amounts of said dicarboxaldehyde are reacted with one mole of said diamine.
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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) | 1982-12-24 | 1983-06-25 | 1983-12-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-12-24 | 1987-06-25 | 1987-12-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-12-24 | 1991-06-25 | 1991-12-25 | $7700.00 | Window Closed / Lapsed |