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US3975331A
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Process for producing aromatic polyamides from amidine derivatives of polyamide forming reactants
Assignee: Bridgestone Firestone Inc
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Filing: 1973-12-20
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Granted: 1976-08-17
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Expires: 1993-12-20
Abstract
Abstract Polyamides, particularly aromatic polyamides and mixed aromatic-aliphatic polyamides, are produced by heating various amidines or amidine derivatives to yield polymer and a volatile low molecular weight amide, such as formamide. The thermally polymerizable composition is an aromatic amidine or salt thereof, e.g. N,N-1,4-phenylene bis-(N',N'-dimethylformamidinium) terephthalate which is heat polymerizable to poly-(p-phenylene terephthalamide); or N-(p-carboxyphenyl)-N',N'-dimethyl formamidine hydrochloride which is heat polymerizable to poly-(p-benzamide).
Inventors
- 👤 John W. Spiewak
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 05:10
CPC Classifications
C; C08; C08G; C08G69/00; C08G69/02; C08G69/26; C08G69/28; C08G69/08; C08G69/12; C08G69/32
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
91 words
A process for forming a filament forming, aromatic polyamide which comprises heating an amidine composition of matter characterized by the group: ##EQU2## to a temperature of at least 225°C where a volatile alkyl amide is evolved, said amidine comprising: a dibasic acid salt of a bis-amidine having the general formula: ##EQU3## wherein Ar is a divalent aromatic radical, R 2 and R 3 are each a lower alkyl radical containing from 1 to 3 carbon atoms, and R 1 is hydrogen or a C 1 - C 3 lower alkyl group.
Claim 2
Dependent Claim
91 words
A process for forming a filament forming, aromatic polyamide which comprises heating an amidine composition of matter characterized by the group: ##EQU2## to a temperature of at least 225°C where a volatile alkyl amide is evolved, said amidine comprising: a dibasic acid salt of a bis-amidine having the general formula: ##EQU3## wherein Ar is a divalent aromatic radical, R 2 and R 3 are each a lower alkyl radical containing from 1 to 3 carbon atoms, and R 1 is hydrogen or a C 1 - C 3 lower alkyl group.
Claim 3
Dependent Claim
94 words
A process of forming a filament forming, aromatic polyamide which comprises heating to a temperature of at least 225°C where a volatile alkyl amide is evolved a polymerizable composition comprising the salt formed from the interaction of equimolar amounts of a. an aromatic bis-alkamidine having the general formula: ##EQU4## wherein Ar is a divalent aromatic radical, R 2 and R 3 are each a lower alkyl radical containing from 1 to 3 carbon atoms, and R 1 is hydrogen or a C 1 - C 3 lower alkyl group; and b. a dicarboxylic acid.
Claim 4
Dependent Claim
94 words
A process of forming a filament forming, aromatic polyamide which comprises heating to a temperature of at least 225°C where a volatile alkyl amide is evolved a polymerizable composition comprising the salt formed from the interaction of equimolar amounts of a. an aromatic bis-alkamidine having the general formula: ##EQU4## wherein Ar is a divalent aromatic radical, R 2 and R 3 are each a lower alkyl radical containing from 1 to 3 carbon atoms, and R 1 is hydrogen or a C 1 - C 3 lower alkyl group; and b. a dicarboxylic acid.
Claim 5
Dependent Claim
16 words
A process in accordance with claim 2 wherein R 2 and R 3 are each methyl.
Claim 6
Dependent Claim
12 words
A process in accordance with claim 2 wherein R 1 is hydrogen.
Claim 7
Dependent Claim
21 words
A process in accordance with claim 2 wherein R 2 and R 3 are each methyl and R 1 is hydrogen.
Claim 8
Dependent Claim
11 words
A process in accordance with claim 2 wherein Ar is phenylene.
Claim 9
Dependent Claim
11 words
A process in accordance with claim 2 wherein Ar is 1,4-phenylene.
Claim 10
Dependent Claim
24 words
A process in accordance with claim 2 wherein Ar is 1,4-phenylene, R 2 and R 3 are each methyl and R 1 is hydrogen.
Claim 11
Dependent Claim
17 words
A process in accordance with claim 2 wherein the dicarboxylic organic acid is a dicarboxylic aliphatic acid.
Claim 12
Dependent Claim
16 words
A process in accordance with claim 2 wherein the dicarboxylic acid is an aromatic dicarboxylic acid.
Claim 13
Dependent Claim
17 words
A process in accordance with claim 10 wherein the aromatic dicarboxylic acid is a phenylene dicarboxylic acid.
Claim 14
Dependent Claim
15 words
A process in accordance with claim 11 wherein the phenylene dicarboxylic acid is terephthalic acid.
Claim 15
Dependent Claim
14 words
A process in accordance with claim 8 wherein the dicarboxylic acid is terephthalic acid.
Claim 16
Dependent Claim
83 words
A process of forming a filament forming, aromatic polyamide which comprises heating to a temperature of at least 225°C where a volatile amide is evolved a polymerizable composition comprising in combination: a. an aromatic bias-alkamidine having the general formula ##EQU5## wherein Ar is a divalent aromatic radical, R 2 and R 3 are a lower alkyl radical containing from 1 to 3 carbon atoms, and R 1 is hydrogen or a C 1 - C 3 lower alkyl group; b. a dicarboxylic acid.
Claim 17
Dependent Claim
83 words
A process of forming a filament forming, aromatic polyamide which comprises heating to a temperature of at least 225°C where a volatile amide is evolved a polymerizable composition comprising in combination: a. an aromatic bias-alkamidine having the general formula ##EQU5## wherein Ar is a divalent aromatic radical, R 2 and R 3 are a lower alkyl radical containing from 1 to 3 carbon atoms, and R 1 is hydrogen or a C 1 - C 3 lower alkyl group; b. a dicarboxylic acid.
Claim 18
Dependent Claim
16 words
A process in accordance with claim 14 wherein R 2 and R 3 are each methyl.
Claim 19
Dependent Claim
12 words
A process in accordance with claim 14 wherein R 1 is hydrogen.
Claim 20
Dependent Claim
21 words
A process in accordance with claim 14 wherein R 2 and R 3 are each methyl and R 1 is hydrogen.
Claim 21
Dependent Claim
11 words
A process in accordance with claim 14 wherein Ar is phenylene.
Claim 22
Dependent Claim
11 words
A process in accordance with claim 14 wherein Ar is 1,4-phenylene.
Claim 23
Dependent Claim
24 words
A process in accordance with claim 14 wherein Ar is 1,4-phenylene, R 2 and R 3 are each methyl and R 1 is hydrogen.
Claim 24
Dependent Claim
17 words
A process in accordance with claim 14 wherein the dicarboxylic organic acid is a dicarboxylic aliphatic acid.
Claim 25
Dependent Claim
16 words
A process in accordance with claim 14 wherein the dicarboxylic acid is an aromatic dicarboxylic acid.
Claim 26
Dependent Claim
17 words
A process in accordance with claim 22 wherein the aromatic dicarboxylic acid is a phenylene dicarboxylic acid.
Claim 27
Dependent Claim
15 words
A process in accordance with claim 23 wherein the phenylene dicarboxylic acid is terephthalic acid.
Claim 28
Dependent Claim
15 words
A process in accordance with claim 20 wherein the dicarboxylic acid is terephthalic acid. .
References Cited (Backward Citations)
US3094511A
Cited
US3475387A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-08-17 | 1980-02-16 | 1980-08-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-08-17 | 1984-02-16 | 1984-08-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-08-17 | 1988-02-16 | 1988-08-17 | $7700.00 | Window Closed / Lapsed |