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US4645823A
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Polyamide preparation from polycarboxylic acid and polyamine with carbodiimide condensing agent
Assignee: Asahi Kasei Corp
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Filing: 1985-09-10
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Granted: 1987-02-24
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Expires: 2005-09-10
Abstract
Abstract A process for preparing polyamides which comprises polycondensing dicarboxylic acids having the following general formula and diamines by using carbodiimides as the condensing agent. ##STR1## wherein X is a group having a valence of (m+2), and C 6-20 carbocyclic group, C 3-20 heterocyclic group, C 2-20 alkyl group, or C 2-20 alkenyl group, the group having at least one carbon-carbon double bond in the position of conjugating to carboxylic acid radical or the group having an α,β-unsaturated ketone structure; Y is --OR or --NRR' wherein R and R' each independently is C 5-20 carbocyclic group, C 1-20 heterocyclic group, C 1-20 alkyl group or substituted group thereof having at least one substituent selected from the group consisting of --OW (wherein W is C 1-12 alkyl group), C 2-12 saturated acyl group, C 2-12 saturated acyloxy group, C 2-12 saturated acylamino group, C 2-12 dialkylamino group, --SW (wherein W is the same as defined above), C 2-12 saturated acylthio group and C 3-12 group having at least one silicon atom; m is 0, 1 or 2; and --COY can be attached to any of the positions ortho, peri, β and γ with respect to the --COOH group.
Inventors
- 👤 Hideo Ai
- 👤 Akihiko Ikeda
- 👤 Yoshio Matsuoka
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 22:49
CPC Classifications
C; C08; C08G; C08G69/00; C08G69/02; C08G69/26; C08G69/32; C08G73/00; C08G73/06; C08G73/10; C08G73/1003; C08G73/1007; C08G69/28; C08G69/42
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
209 words
A process for preparing a polyamide which comprises polycondensing a dicarboxylic acid having the following general formula: ##STR17## wherein X is a group having a valence of (m+2), and is a C 6-20 carbocyclic group, a C 3-20 heterocyclic group, a C 2-20 alkyl group or a C 2-20 alkenyl group, the group having at least one carbon-carbon double bond in the position of conjugating to the carboxylic acid radical or the group having an α, β-unsaturated ketone structure; Y is --OR or --NRR', wherein each of R and R' is independently a C 5-20 carbocyclic group, a C 1-20 heterocyclic group, a C 1-20 alkyl group or substituted group thereof having at least one substituent selected from the group consisting of a C 1-12 alkoxy group, a C 2-12 saturated acyl group, a C 2-12 saturated acyloxy group, a C 2-12 saturated acylamino group, a C 2-12 dialkylamino group, a C 1-12 alkylthio group, a C 2-12 saturated acylthio group and a C 3-12 group having at least one silicon atom; m is 0, 1 or 2; and --COY is attached to any of the positions ortho, peri, β and γ with respect to the --COOH group, with a diamine by using a carbodiimide as the condensing agent.
Claim 2
Dependent Claim
209 words
A process for preparing a polyamide which comprises polycondensing a dicarboxylic acid having the following general formula: ##STR17## wherein X is a group having a valence of (m+2), and is a C 6-20 carbocyclic group, a C 3-20 heterocyclic group, a C 2-20 alkyl group or a C 2-20 alkenyl group, the group having at least one carbon-carbon double bond in the position of conjugating to the carboxylic acid radical or the group having an α, β-unsaturated ketone structure; Y is --OR or --NRR', wherein each of R and R' is independently a C 5-20 carbocyclic group, a C 1-20 heterocyclic group, a C 1-20 alkyl group or substituted group thereof having at least one substituent selected from the group consisting of a C 1-12 alkoxy group, a C 2-12 saturated acyl group, a C 2-12 saturated acyloxy group, a C 2-12 saturated acylamino group, a C 2-12 dialkylamino group, a C 1-12 alkylthio group, a C 2-12 saturated acylthio group and a C 3-12 group having at least one silicon atom; m is 0, 1 or 2; and --COY is attached to any of the positions ortho, peri, β and γ with respect to the --COOH group, with a diamine by using a carbodiimide as the condensing agent.
Claim 3
Dependent Claim
13 words
A process according to claim 1, wherein the polycondensation is a solution polycondensation.
Claim 4
Dependent Claim
21 words
A process according to claim 2, wherein the solution polycondensation is carried out in the presence of an aprotic polar solvent.
Claim 5
Dependent Claim
22 words
A process according to claim 1, wherein the carbodiimide is one that urea produced from the carbodiimide is insoluble in acidic water.
Claim 6
Dependent Claim
16 words
A process according to claim 4, wherein the carbodiimide is N,N'-dicyclohexylcarbodiimide, N,N'-diethylcarbodiimide, N,N'-diisopropylcarbodiimide, ethylcyclohexylcarbodiimide or N,N'-diphenylcarbodiimide.
Claim 7
Dependent Claim
11 words
A process according to claim 5, wherein the carbodiimide is N,N'-dicyclohexylcarbodiimide.
Claim 8
Dependent Claim
12 words
A process according to claim 5, wherein the carbodiimide is N,N'- diisopropylcarbodiimide.
Claim 9
Dependent Claim
22 words
A process according to claim 1, wherein the carbodiimide is one that urea produced from the carbodiimide is soluble in acidic water.
Claim 10
Dependent Claim
14 words
A process according to claim 8, wherein the carbodiimide is 1-ethyl-3-(3-dimethylaminoprpyl)carbodiimide, 1-cyclohexyl-3-(3-dimethylaminopropyl)carbodiimide or carbodiimide.
Claim 11
Dependent Claim
10 words
A process according to claim 1, wherein m is 0.
Claim 12
Dependent Claim
10 words
A process according to claim 1, wherein m is 1.
Claim 13
Dependent Claim
10 words
A process according to claim 1, wherein m is 2.
Claim 14
Dependent Claim
14 words
A process according to claim 1, wherein X is a C 6-20 carbocyclic group.
Claim 15
Dependent Claim
15 words
A process according to claim 13, wherein the carbocyclic group is an aromatic carbocyclic group.
Claim 16
Dependent Claim
14 words
A process according to claim 1, wherein X is a C 3-20 heterocyclic group.
Claim 17
Dependent Claim
14 words
A process according to claim 1, wherein X is a C 2-20 alkyl group.
Claim 18
Dependent Claim
14 words
A process according to claim 1, wherein X is a C 2-20 alkenyl group.
Claim 19
Dependent Claim
27 words
A process according to claim 1, wherein X is a group having at least one carbon-carbon double bond in the position of conjugating to carboxylic acid radical.
Claim 20
Dependent Claim
16 words
A process according to claim 1, wherein X is a group having an α,β-unsaturated ketone structure.
Claim 21
Dependent Claim
19 words
A process according to claim 1, wherein each of R and R' a independently a C 5-20 carbocyclic group.
Claim 22
Dependent Claim
19 words
A process according to claim 1, wherein each of R and R' is independently a C 1-20 heterocyclic group.
Claim 23
Dependent Claim
19 words
A process according to claim 1, wherein each of R and R' is independently a C 1-20 alkyl group.
Claim 24
Dependent Claim
95 words
A process according to claim 1, wherein each of R and R' is independently a substituted C 5-20 carbocyclic group, a substituted C 1-20 heterocyclic group or a substituted C 1-20 alkyl group, which has at least one substituent selected from the group consisting of a C 1-12 alkoxy group, a C 2-12 saturated acyl group, a C 2-12 saturated acyloxy group, a C 2-12 saturated acylamino group, a C 2-12 dialkylamino group, a C 1-12 alkylthio group, a C 2-12 saturated acylthio group and a C 3-12 group having at least one silicon atom.
Claim 25
Dependent Claim
13 words
A process according to claim 1, wherein the diamine is an aromatic diamine.
Claim 26
Dependent Claim
15 words
A process according to claim 1, wherein the diamine has at least one silicon atom.
Claim 27
Dependent Claim
14 words
A polyamide having terminal acylurea groups and produced by the method of claim 1.
Claim 28
Dependent Claim
91 words
A process according to claim 1 which is conducted at a reaction temperature of from -20° C. to 80° C. and wherein the molar ratio of the condensing agent to the diamine is at least 2 when the dicarboxylic acid is in excess with respect to the diamine, the molar ratio of the condensing agent to the dicarboxylic acid being at least 2 when the diamine is in excess with respect to the dicarboxylic acid, and the molar ratio of the dicarboxylic acid to the diamine being from 0.7 to 1.3.
Claim 29
Dependent Claim
14 words
A polyamide having terminal acylurea groups and produced by the method of claim 2.
Claim 30
Dependent Claim
218 words
A polyamide having terminal groups, from 10 to 80% of which, based upon the total amount of polymer terminals, have acylurea structure, the polyamide being a polycondensate of a dicarboxylic acid of the formula: ##STR18## wherein X is a group having a valence of (m+2), and is a C 6-20 carbocyclic group, a C 3-20 heterocyclic group, a C 2-20 alkyl group or a C 2-20 alkenyl group, the group having at least one carbon-carbon double bond in the position of conjugating to the carboxylic acid radical or the group having a α,β-unsaturated ketone structure; Y is --OR or --NRR', wherein each of R and R' is independently a C 5-20 carbocyclic group, a C 1-20 heterocyclic group, a C 1-20 alkyl group or a substituted group thereof having at least one subsituent selected from the group consisting of a C 1-12 alkoxy group, a C 2-12 saturated acyl group, a C 2-12 saturated acyloxy group, a C 2-12 saturated acylamino group, a C 2-12 dialkylamino group, a C 1-12 alkylthio group, a C 2-12 saturated acylthio group and a C 3-12 group having at least one silicon atom; m is 0, 1 or 2; and --COY is attached to any of the positions ortho, peri, β and γ with respect to the --COOH group, with a diamine.
Claim 31
Dependent Claim
218 words
A polyamide having terminal groups, from 10 to 80% of which, based upon the total amount of polymer terminals, have acylurea structure, the polyamide being a polycondensate of a dicarboxylic acid of the formula: ##STR18## wherein X is a group having a valence of (m+2), and is a C 6-20 carbocyclic group, a C 3-20 heterocyclic group, a C 2-20 alkyl group or a C 2-20 alkenyl group, the group having at least one carbon-carbon double bond in the position of conjugating to the carboxylic acid radical or the group having a α,β-unsaturated ketone structure; Y is --OR or --NRR', wherein each of R and R' is independently a C 5-20 carbocyclic group, a C 1-20 heterocyclic group, a C 1-20 alkyl group or a substituted group thereof having at least one subsituent selected from the group consisting of a C 1-12 alkoxy group, a C 2-12 saturated acyl group, a C 2-12 saturated acyloxy group, a C 2-12 saturated acylamino group, a C 2-12 dialkylamino group, a C 1-12 alkylthio group, a C 2-12 saturated acylthio group and a C 3-12 group having at least one silicon atom; m is 0, 1 or 2; and --COY is attached to any of the positions ortho, peri, β and γ with respect to the --COOH group, with a diamine.
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) | 1990-02-23 | 1990-08-25 | 1991-02-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-02-23 | 1994-08-25 | 1995-02-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-02-23 | 1998-08-25 | 1999-02-24 | $7700.00 | Window Closed / Lapsed |