IP Library Granted Patent US 10,683,258
Granted Patent B2
US 10,683,258 · App. 15/764,596 · Granted Jun 16, 2020

Composition made of amino acid or ester with polymer quality and methods for obtaining same

Inventors: Thierry Briffaud (Bernay, FR); Jean-Luc Couturier (Lyons, FR); Jean-Luc Dubois (Millery, FR); Jean-François Devaux (Soucieu en Jarrest, FR)
Assignee: ARKEMA FRANCE
C07C227/04C07C227/40C08G69/04C08G69/08
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Quick Facts
Patent No.
US 10,683,258
App. No.
15/764,596
Granted
Jun 16, 2020
Kind
B2
Abstract

The present invention relates to a composition which comprises at least one α,ω-amino-alkanoic acid or ester and at least one alkanoic ester or acid, characterised in that: the α,ω-amino-alkanoic acid or ester has formula H 2 N—(CH 2 ) n- COOR, wherein n=9 to 13 and R is an alkyl group or a hydrogen; the alkanoic ester or acid has formula R 1 —COOR 2 , wherein R 1 is a straight or branched alkyl group with formula C m H 2m+1 or C m H 2m−3 , wherein m=6 to 20 and R 2 is an alkyl group or a hydrogen; the molar ratio between the alkanoic acid(s) or ester(s) and the α,ω-amino-alkanoic acid(s) or ester(s) is in the range from 0.001 to 0.4%. The present invention also relates to novel methods for obtaining such a composition.

Claims (16)

1. A composition comprising at least one α,ω-aminoalkanoic acid or ester and at least one alkanoic acid or ester, wherein:

the α,ω-aminoalkanoic ester or acid has the formula H 2 N—(CH 2 ) n —COOR with n=9 to 13 and R is an alkyl group or a hydrogen,

the alkanoic acid or ester has the formula R 1 —COOR 2 with R 1 being a linear or branched alkyl group of formula C m H 2m+1 or C m H 2m−1 or C m H 2m−3 where m=6 to 20 and R 2 is an alkyl group or a hydrogen,

the molar ratio between alkanoic acid(s) or ester(s) and α,ω-aminoalkanoic ester(s) or acid(s) is in the range of from 0.001% to 0.4%.

2. The composition as claimed in claim 1 , wherein n=10 or 11, and R is a methyl or ethyl or butyl group or a hydrogen.

3. The composition as claimed in claim 1 , wherein R 1 is a linear alkyl group of composition C n−1 H 2n−1 and R 2 is a methyl or ethyl group or a hydrogen.

4. The composition as claimed in claim 1 , wherein the molar ratio between alkanoic acid(s) or ester(s) and α,ω-aminoalkanoic ester(s) or acid(s) is in the range of from 0.01% to 0.2%.

5. The composition as claimed in claim 1 , wherein it also comprises an acid nitrile or a nitrile ester of formula NC—(CH 2 ) (n−1) —COOR, in which the molar ratio of nitrile relative to the α,ω-aminoalkanoic ester or acid is in the range of from 0.0001% to 0.5%.

6. The composition as claimed in claim 1 , wherein it also comprises a secondary amine of formula ROOC—(CH 2 ) n —NH—(CH 2 ) n —COOR, in which the molar ratio relative to the α,ω-aminoalkanoic ester or acid is in the range of from 0.0001% to 1%.

7. The composition as claimed in claim 1 , wherein it also comprises ROOC—(CH 2 ) n —NH—CO—(CH 2 ) n —NH 2 dimer, the molar ratio of dimer relative to the α,ω-aminoalkanoic ester or acid being in the range of from 0.0001% to 5%.

8. The composition as claimed in claim 1 , wherein it also comprises at least one compound chosen from: compounds that are inert with respect to the polymerization, alcohols, water, and mixtures thereof.

9. The composition as claimed in claim 8 , wherein the compounds that are inert with respect to the polymerization are chosen from: aromatic hydrocarbons; aliphatic hydrocarbons; an aliphatic fraction; an ether; and mixtures thereof.

10. The composition as claimed in claim 8 , wherein the alcohols are chosen from methanol, ethanol, butanol, and mixtures thereof.

11. The composition as claimed in claim 8 , wherein the content of inert compounds, of alcohol and/or of water is less than 90%, by weight relative to the total weight of the composition.

12. The composition as claimed in claim 1 , wherein the content of α,ω-aminoalkanoic ester or acid is greater than 10%, by weight relative to the total weight of the composition.

13. A polymer, in particular polyamide, obtained by polymerization of the composition of claim 1 , wherein the degree of polymerization thereof is greater than 80.

Assignments (2)
CHANGE OF ADDRESS Recorded Jul 4, 2025
From: ARKEMA FRANCE
To: ARKEMA FRANCE
Reel/Frame 071814/0739 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 26, 2018
From: BRIFFAUD, THIERRY; COUTURIER, JEAN-LUC; DUBOIS, JEAN-LUC; DEVAUX, JEAN-FRANCOIS
To: ARKEMA FRANCE
Reel/Frame 045647/0633 →