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

Patent metadata

Field	Value
Publication number	US-10683258-B2
Application number	US-201615764596-A
Country	US
Kind code	B2
Filing date	Sep 28, 2016
Priority date	Sep 30, 2015
Publication date	Jun 16, 2020
Grant date	Jun 16, 2020

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 H2N—(CH2)n-COOR, wherein n=9 to 13 and R is an alkyl group or a hydrogen; the alkanoic ester or acid has formula R1—COOR2, wherein R1 is a straight or branched alkyl group with formula CmH2m+1 or CmH2m−3, wherein m=6 to 20 and R2 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.

First claim

The invention claimed is:

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.

Assignees

• Arkema France

Inventors

• Briffaud Thierry
• Couturier Jean-Luc
• Dubois Jean-Luc
• Devaux Jean-François

Classifications

• C07C227/04 Primary

  Formation of amino groups in compounds containing carboxyl groups · CPC title

• C08G69/04

  Preparatory processes · CPC title

• C07C227/40

  Separation; Purification · CPC title

• C08G69/08

  derived from amino-carboxylic acids · CPC title

• C07C229/08

  the nitrogen atom of the amino group being further bound to hydrogen atoms · CPC title