NOVEL POLYAMIDE, PROCESS FOR PREPARING SAME AND USES THEREOF

• US 20140135449A1
• Filed: 07/05/2012
• Published: 05/15/2014
• Est. Priority Date: 07/08/2011
• Status: Active Grant

• Current Assignee: Specialty Operations France
• Original Assignee: Rhodia Operations (Solvac SA)
• Inventors: Jeol, Stphane
• Granted Patent: US 9,150,691 B2
• Time in Patent Office: Days
• US Class Current: 524/606
• CPC Class Codes: C08G 69/26 derived from polyamines and polycarboxylic acids
• CPC Class Codes: C08G 69/265 from at least two different diamines or at least two different dicarboxylic acids
• CPC Class Codes: C08G 69/40 Polyamides containing oxygen in the form of ether groups C08G69/12, C08G69/32 take precedence

Abstract

The present invention relates to a novel polyamide synthesized from biosourced monomers. The novel polyamide comprises the repeating unit of formula I below:

• • in which
    • A represents a covalent bond or a divalent hydrocarbon-based group chosen from saturated or unsaturated aliphatics, saturated or unsaturated cycloaliphatics, aromatics comprising at least 5 carbon atoms, arylaliphatics and alkylaromatics;
    • X represents a divalent group of formula II or III below:

The present invention also relates to the process for preparing the said polyamide, to its uses, and to articles and compositions comprising the said polyamide.

Claims

1. A polyamide comprising the repeating unit of formula I below:

2. The polyamide according to claim 1, in which A is chosen from linear or branched alkyl groups containing from 1 to 36 carbon atoms.

3. The polyamide according to claim 1, in which A is chosen from —

(CH₂)₄—

, —

(CH₂)₈— and

—

(CH₂)₁₀—

.

4. The polyamide according to claim 1, in which A is a divalent aromatic hydrocarbon-based group comprising from 6 to 18 carbon atoms.

5. The polyamide according to claim 1, in which X is the divalent group of formula II.

6. The polyamide according to any one of claim 11, in which X is the divalent group of formula III.

7. The polyamide according to claim 6, in which X is the trans stereoisomer.

8. The polyamide according to claim 1, characterized in that it is a homopolyamide consisting entirely of the repeating unit of formula I.

9. The polyamide according to claim 1, characterized in that it is a copolymer comprising other repeating units different from the unit of formula I, the said repeating units different from the unit of formula I originating from comonomers, dicarboxylic acids, diamines, amino acids and/or lactams.

10. A process for preparing a polyamide according to claim 1, characterized in that it comprises a polycondensation reaction between:

at least one dicarboxylic acid or at least one carboxylic acid diester or at least one dinitrile of respective formulae IV, IV′ and

IV″

below;

HOOC-A-COOH  

 

(IV);

ROOC-A-COOR  

 

(IV′

),

with R being a C1-C4 alkyl;

NC-A-CN  

 

(IV″

)

in which

A represents a covalent bond or a divalent hydrocarbon-based group chosen from saturated or unsaturated aliphatics, saturated or unsaturated cycloaliphatics, aromatics comprising at least 5 carbon atoms, arylaliphatics and alkylaromatics; and

at least one diamine of formula V below;

H₂N—

X—

NH₂  

 

(V)

in which X represents a divalent group of formula II or III below;

11. The process according to claim 10, characterized in that the at least one diamine of formula V is biosourced according to standard ASTM D6866.

12. The process according to claim 10, characterized in that it comprises a polycondensation reaction between:

at least one dicarboxylic acid of formula IV below;

HOOC-A-COOH  

 

(IV);

and

at least one diamine of formula V below;

H₂N—

X—

NH₂  

 

(V)

13. The process according to claim 10, characterized in that the at least one dicarboxylic acid of formula IV is biosourced according to standard ASTM D6866.

14. A process for making articles comprising the polyamide according to claim 1, the process comprising moulding, injection-moulding, injection/blow-moulding, extrusion/blow-moulding, extrusion or spinning.

15. An article obtained from the polyamide according to claim 1, the said article being moulded or extruded pieces, yarns, fibres, filaments or films.

16. A composition comprising the polyamide according to claim 1, and optionally further comprising reinforcing fillers and/or additives.

17. The polyamide according to claim 2, in which A is a linear alkyl group containing from 4 to 10 carbon atoms.

18. The polyamide according to claim 4, in which A is the group 1,4-benzene.