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US4238585A
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Aryl amine terminated polysulfide polymers, related compounds and processes for their preparation
Assignee: ATK Launch Systems LLC
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Filing: 1979-08-10
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Granted: 1980-12-09
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Expires: 1999-08-10
Abstract
Abstract Fully and partially aryl amine terminated polysulfide polymers and processes for their preparation and use are disclosed. The fully aryl amine terminated products are curable with isocyanates to high molecular weight polymers and are thus useful in molding and casting as well as in sealants. The partially aryl amine terminated polymers may be further reacted with polyisocyanates to form thiol terminated polysulfide polymers containing urea chain segments. These compounds are curable in the fashion of standard polysulfide polymers to form firmer polymers. The partially aryl amine terminated polymers may be also chain extended with isocyanate terminated urethane prepolymers. These block copolymers may be cured by standard SH terminated polysulfide polymer cure methods to prepare sealants of exceptional resiliency and weather resistance.
Inventors
- 👤 Eugene R. Bertozzi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 22:02
CPC Classifications
C; C08; C08G; C08G75/00; C08G75/14; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/64; C08G18/6453
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
92 words
A compound of the formula: (H.sub.2 N).sub.a --Ar--S.sub.x --R--S.sub.x --.sub.n R--Y wherein Y is --SH or --S x --Ar--(NH 2 ) a ; Ar is an a +1 valent radical derived by removal of a +1 nuclear hydrogens from a substituted or unsubstituted aryl moiety either carbocyclic or heterocyclic and having 1 or 2 aromatic rings; R is a hydrocarbon, oxahydrocarbon, or thiahydrocarbon radical; a is 1 or 2; n is about 4 to about k×10 3 wherein k is 1 to about 10 and x is from 1.8 to about 4.
Claim 2
Dependent Claim
92 words
A compound of the formula: (H.sub.2 N).sub.a --Ar--S.sub.x --R--S.sub.x --.sub.n R--Y wherein Y is --SH or --S x --Ar--(NH 2 ) a ; Ar is an a +1 valent radical derived by removal of a +1 nuclear hydrogens from a substituted or unsubstituted aryl moiety either carbocyclic or heterocyclic and having 1 or 2 aromatic rings; R is a hydrocarbon, oxahydrocarbon, or thiahydrocarbon radical; a is 1 or 2; n is about 4 to about k×10 3 wherein k is 1 to about 10 and x is from 1.8 to about 4.
Claim 3
Dependent Claim
17 words
A compound as defined in claim 1 wherein Y is --S x --Ar--(NH 2 ) a .
Claim 4
Dependent Claim
11 words
A compound as defined in claim 1 wherein Y is --SH.
Claim 5
Dependent Claim
31 words
A compound as defined in claims 2 or 3 wherein Ar is a radical derived from benzene or alkyl benzene, a is 1 and n is about 4 to about 23.
Claim 6
Dependent Claim
64 words
A process for the preparation of a compound of the formula: (H.sub.2 N).sub.a --Ar--S.sub.x --R--S.sub.x).sub.n R--S.sub.x --Ar--(NH.sub.2).sub.a wherein Ar; R; a; n and x are as defined in claim 1 which comprises treating a compound of the formula: (O.sub.2 N).sub.a --Ar--Hal wherein Hal is Cl, Br or I; together with a compound of the formula: Hal--R--Hal with sodium polysulfide in a substantially aqueous medium.
Claim 7
Dependent Claim
73 words
A process for the preparation of a compound of the formula: (H.sub.2 N).sub.a --Ar--S.sub.x --R--S.sub.x).sub.n --R--SH wherein Ar; R; a; n and x are as defined in claim 5 which comprises preparing by the process of claim 5 a compound of the formula: (H.sub.2 N).sub.a --Ar--S.sub.x --R--S.sub.x).sub.n' R--S.sub.x Ar--(NH.sub.2).sub.a wherein n' is a number greater than n and treating said compound with SH - and SO 3 = in a substantially aqueous environment.
Claim 8
Dependent Claim
109 words
A process for the preparation of a compound of the formula: (H.sub.2 N).sub.a --Ar--S.sub.x --R--S.sub.x).sub.n R--S.sub.x --Ar--(NH.sub.2).sub.a wherein Ar; R; a; n and x are as defined in claim 1 which comprises treating a compound of the formula: Hal--R--Hal wherein Hal is Cl, Br or I with sodium polysulfide in a substantially aqueous medium to prepare a compound of the formula: HO--R--S.sub.x --R].sub.n' S.sub.x --R--OH wherein n' is sufficient to give molecular weight values of from 1×10 4 to k×10 5 wherein k is about 1 to 10 and treating the compound so produced with a compound of the formula: (H.sub.2 N).sub.a 13 Ar--S--S--Ar--(NH.sub.2).sub.a in a substantially aqueous environment.
Claim 9
Dependent Claim
68 words
A process for the preparation of a compound of the formula: (H.sub.2 N).sub.a --Ar--S.sub.x --R--S.sub.x).sub.n --R--SH wherein Ar; R; a; n and x are as defined in claim 5 which comprises preparing by the process of claim 5 a compound of the formula: (H.sub.2 N).sub.a --Ar--S.sub.x --R--S.sub.x).sub.n R--S.sub.x Ar--(NH.sub.2).sub.a and treating said compound with a thiol terminated liquid polysulfide polymer of the formula: HS--R--S.sub.x).sub.n R--SH at elevated temperature.
Claim 10
Dependent Claim
108 words
A process for the preparation of a compound of the formula: (H.sub.2 N).sub.a --AR--S.sub.x --R--S.sub.x).sub.n R--S.sub.x --Ar--(NH.sub.2).sub.a wherein Ar; R; a; n and x are as defined in claim 1 which comprises treating a compound of the formula: Hal--R--Hal wherein Hal is Cl, Br or I with sodium polysulfide in a substantially aqueous medium to prepare a compound of the formula: HO--R--S.sub.x --R].sub.n' S.sub.x --R--OH wherein n' is sufficient to give molecular weight values of from 1×10 4 to k×10 5 wherein k is about 1 to 10 and treating the compound so produced with a compound of the formula: (H.sub.2 N).sub.a --Ar--S.sup.- in a substantially aqueous environment.
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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) | 1983-12-09 | 1984-06-09 | 1984-12-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-12-09 | 1988-06-09 | 1988-12-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-12-09 | 1992-06-09 | 1992-12-09 | $7700.00 | Window Closed / Lapsed |