Polyamide, process for preparing same and uses thereof

• US 9,150,691 B2
• Filed: 07/05/2012
• Issued: 10/06/2015
• Est. Priority Date: 07/08/2011
• Status: Active Grant

• Current Assignee: Specialty Operations France
• Original Assignee: Rhodia Operations (Solvac SA)
• Inventors: Jeol, Stphane
• Primary Examiner(s): Chung, Susannah
• Assistant Examiner(s): Butcher, Robert T
• Application Number:
  US14/131,448
• Publication Number:
  US 20140135449A1
• Time in Patent Office: 1,188 Days
• Field of Search: None
• US Class Current: 1/1
• 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 a linear alkyl group containing from 1 to 36 carbon atoms.

3. The polyamide according to claim 1, in which A is selected from the group consisting of —

(CH₂)₄—

, —

(CH₂)₈— and

—

(CH₂)₁₀—

.

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

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

6. The polyamide according to claim 5, in which X is the trans stereoisomer.

7. The polyamide according to claim 1, wherein the polyamide is a homopolyamide consisting entirely of the repeating unit of formula I.

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

9. A process for preparing a polyamide according to claim 1, the process comprising 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 selected from the group consisting of linear saturated and unsaturated aliphatics, saturated and unsaturated cycloaliphatics, 1,4-benzene and 2,6-naphthalene, —

(CH₂)_n—

Ph-(CH₂)_n′

—

with n and n′

being integers, 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;

10. The process according to claim 9, wherein the at least one diamine of formula V is biosourced according to standard ASTM D6866.

11. The process according to claim 9, wherein the process 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).

12. The process according to claim 9, wherein the at least one dicarboxylic acid of formula IV is biosourced according to standard ASTM D6866.

13. 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.

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

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

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

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