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US4452974A
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Preparation of hexamethylenediamine/adipic acid/dimer acid copolyamide
Assignee: Rhone Poulenc Industries SA
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Filing: 1982-09-24
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Granted: 1984-06-05
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Expires: 2002-09-24
Abstract
Abstract Flexible, homogeneous and transparent copolyamides comprise the polycondensation products of adipic acid, fatty acid dimer and hexamethylenediamine, the molar ratio of weight adipic acid to weight of total acid in each ranging from about 0.5 to 0.99, and that point obtained by plotting, along the abscissa, such molar fraction of adipic acid versus, along the ordinate, any individual copolyamide melting point, falling within that area A B C D outlined on the attached Figure of Drawing. The subject copolyamides are prepared either by polycondensing a homogenized prepolymer thereof, or by directly copolycondensing a homogeneous, inert solvent solution of monomers. The homogeneous and transparent copolyamides exhibit improved flexibility and high tenacity coupled with good resistance to hydrolysis and good heat resistance, with the copolyamides being useful for providing shaped articles such as moldings, films or filaments of marked uniformity via injection molding, extrusion or spinning.
Inventors
- 👤 Jean Goletto
- 👤 Jean Coquard
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 11:44
CPC Classifications
C; C08; C08G; C08G69/00; C08G69/02; C08G69/26; C08G69/34
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
159 words
A process for the preparation of a copolyamide comprising the polycondensation product of adipic acid, fatty acid dimer and hexamethylene diamine, wherein the molar fraction of adipic acid relative to the total amount of acid and the copolyamide melting point are such that the point obtained by plotting said molar fraction of adipic acid along the abscissa versus the copolyamide melting point along the ordinate falls within the area A B C D outlined on the accompanying FIGURE of Drawing, and wherein the molar ratio of adipic acid to the total amount of acid in the copolyamide ranges from about 0.5 to 0.99, comprising preparing a prepolymer thereof in a heterogeneous medium from a mixture of adipic acid, dimeric acid and hexamethylenediamine, or corresponding salts thereof, thence homogenizing such prepolymer under such conditions that the state of equilibrium of the amidification reaction remains essentially unchanged, and then converting the resulting homogeneous prepolymer into a polycondensate of high molecular weight.
Claim 2
Dependent Claim
159 words
A process for the preparation of a copolyamide comprising the polycondensation product of adipic acid, fatty acid dimer and hexamethylene diamine, wherein the molar fraction of adipic acid relative to the total amount of acid and the copolyamide melting point are such that the point obtained by plotting said molar fraction of adipic acid along the abscissa versus the copolyamide melting point along the ordinate falls within the area A B C D outlined on the accompanying FIGURE of Drawing, and wherein the molar ratio of adipic acid to the total amount of acid in the copolyamide ranges from about 0.5 to 0.99, comprising preparing a prepolymer thereof in a heterogeneous medium from a mixture of adipic acid, dimeric acid and hexamethylenediamine, or corresponding salts thereof, thence homogenizing such prepolymer under such conditions that the state of equilibrium of the amidification reaction remains essentially unchanged, and then converting the resulting homogeneous prepolymer into a polycondensate of high molecular weight.
Claim 3
Dependent Claim
105 words
The process as defined by claim 1, wherein said mixture consists essentially of a mixture of adipic acid, dimeric acid and hexamethylenediamine, or corresponding salts thereof, the content of amine groups and of carboxylic acid groups therein differing by no more than 5% in absolute value, and comprising gradually and uniformly heating and homogenizing the prepolymer for a period of from 0.5 to 5 hours at a temperature of from 270° to 290° C. under a water vapor pressure between 13 and 25 bars, during which period the state of equilbrium of the amidification reaction is maintained essentially unchanged, and then polycondensing such homogenized prepolymer.
Claim 4
Dependent Claim
24 words
The process as defined by claim 2, wherein said content of amine groups and of carboxylic acid groups differs by not more than 1%.
Claim 5
Dependent Claim
36 words
The process as defined by claim 2, wherein said mixture essentially consists of an emulsion of the salt of the dimeric acid with hexamethylenediamine in an aqueous solution of the salt of adipic acid with hexamethylenediamine.
Claim 6
Dependent Claim
18 words
The process as defined by claim 4, the reactants comprising said mixture being present in essentially stoichiometric amounts.
Claim 7
Dependent Claim
17 words
The process as defined by claim 5, the mixture being adjusted to stoichiometry pursuant to pH measurement.
Claim 8
Dependent Claim
109 words
The process as defined by claim 1, wherein said mixture consists essentially of a stoichiometrically unbalanced mixture of adipic acid, dimeric acid and hexamethylenediamine, or corresponding salts thereof, the content of amine groups and of carboxylic acid groups therein differing by no more than 5%, and comprising gradually and uniformly heating and homogenizing the prepolymer for a period of from 10 minutes to 2 hours at a temperature of from 265° C. to 290° C., and thence gradually adding thereto such reactant or reactants as to adjust the mixture to stoichiometry, at a temperature of from 260° to 290° C., until a copolycondensate having the desired viscosity is obtained.
Claim 9
Dependent Claim
24 words
The process as defined by claim 7, wherein the stoichiometric excess of the amine reactant or acid reactant is from 5 to 20 mol%.
Claim 10
Dependent Claim
16 words
The process as defined by claim 8, wherein the reactant present in stoichiometric deficiency is hexamethylenediamine.
Claim 11
Dependent Claim
23 words
The process as defined by claim 8, wherein the homogenization stage is carried out at a temperature of from 270° and 285° C.
Claim 12
Dependent Claim
165 words
A process for the preparation of a copolyamide comprising the polycondensation product of adipic acid, fatty acid dimer and hexamethylenediamine, wherein the molar fraction of adipic acid relative to the total amount of acid and the copolyamide melting point are such that the point obtained by plotting said molar fraction of adipic acid along the abscissa versus the copolyamide melting point along the ordinate falls within the area A B C D outlined on the accompanying Figure of Drawing, and wherein the molar ratio of adipic acid to the total amount of acid in the copolyamide ranges from about 0.5 to 0.99, comprising directly polycondensing, at a temperature of from 150° to 300° C. in a homogeneous medium, a mixture of adipic acid, dimeric acid and hexamethylenediamine, said medium including an inert organic solvent for the three-component starting admixture, or for the corresponding salts and oligomers having a molecular weight of less than 5,000 of adipic acid and hexamethylenediamine, and of dimeric acid and hexamethylenediamine.
Claim 13
Dependent Claim
165 words
A process for the preparation of a copolyamide comprising the polycondensation product of adipic acid, fatty acid dimer and hexamethylenediamine, wherein the molar fraction of adipic acid relative to the total amount of acid and the copolyamide melting point are such that the point obtained by plotting said molar fraction of adipic acid along the abscissa versus the copolyamide melting point along the ordinate falls within the area A B C D outlined on the accompanying Figure of Drawing, and wherein the molar ratio of adipic acid to the total amount of acid in the copolyamide ranges from about 0.5 to 0.99, comprising directly polycondensing, at a temperature of from 150° to 300° C. in a homogeneous medium, a mixture of adipic acid, dimeric acid and hexamethylenediamine, said medium including an inert organic solvent for the three-component starting admixture, or for the corresponding salts and oligomers having a molecular weight of less than 5,000 of adipic acid and hexamethylenediamine, and of dimeric acid and hexamethylenediamine.
Claim 14
Dependent Claim
20 words
The process as defined by claim 1, wherein said solvent has a boiling point of from 170° to 250° C.
Claim 15
Dependent Claim
12 words
The process as defined by claim 12, wherein said solvent is N-methylpyrrolidone.
Claim 16
Dependent Claim
17 words
The process as defined by claim 1, wherein said copolycondensation temperature ranges from 190° to 280° C.
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) | 1987-06-05 | 1987-12-05 | 1988-06-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-06-05 | 1991-12-05 | 1992-06-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-06-05 | 1995-12-05 | 1996-06-05 | $7700.00 | Window Closed / Lapsed |