Copolyamide, composition comprising such a copolyamide and uses thereof

Patent metadata

Field	Value
Publication number	US-11384200-B2
Application number	US-201715812653-A
Country	US
Kind code	B2
Filing date	Nov 14, 2017
Priority date	Jun 20, 2008
Publication date	Jul 12, 2022
Grant date	Jul 12, 2022

Abstract

The present invention relates to a copolyamide comprising at least two units and corresponding to the following general formula:A/(diamine)·(Cw diacid),in which:the diamine is a cycloaliphatic diamine,w represents the number of carbon atoms of the diacid,A is chosen from a unit obtained from an amino acid or from a lactam and a unit corresponding to the formula (Cx diamine)·(Cy diacid), with x representing the number of carbon atoms of the diamine and y representing the number of carbon atoms of the diacid,and in which at least one of the monomers chosen from A and the Cw diacid is obtained, in all or part, from renewable starting materials according to Standard ASTM D6866.The invention also relates to a composition comprising this copolyamide and to the use of this copolyamide and of such a composition.

First claim

The invention claimed is:

1. A copolyamide comprising at least two units and having the formula:
A/(diamine)·(C w diacid),

in which:
the diamine is a cycloaliphatic diamine,
w represents the number of carbon atoms of the diacid, and
A is a unit obtained from an amino acid that is 9-aminononanoic acid, 10-aminodecanoic acid, 12-aminododecanoic acid, or 11-aminoundecanoic acid,

the copolyamide having a molar content of A of up to 64%,
and having a glass transition temperature of at least 110° C.,
and in which at least one of the monomers A and the Cw diacid are obtained, in all or part, from renewable starting materials according to Standard ASTM D6866 in order for the content, expressed as percentage, of renewable organic carbon in the copolyamide, denoted % C renew.org , of greater than or equal to 54%, the content % C renew.org corresponding to the following equation (I):

%
⁢

⁢

C

renew
.
org

=

∑
i

⁢

Fi
×
Ci

+

∑
k

⁢

Fk
×

Ck
′

(

∑
j

⁢

Fj
×
Cj

+

∑
i

⁢

Fi
×
Ci

+

∑
k

⁢

Fk
×
Ck

)

×
100

⁢

(
I
)

with i=monomer(s) resulting from 100% renewable starting materials, within the meaning of Standard ASTM D6866
j=monomer(s) resulting from 100% fossil starting materials, within the meaning of Standard ASTM D6866
k=monomer(s) resulting in part from renewable starting materials, within the meaning of Standard ASTM D6866
Fi, Fj, Fk=respective molar fraction(s) of the monomers i, j and k in the copolyamide
Ci, Cj, Ck=respective number of carbon atoms of the monomers i, j and k in the copolyamide,
Ck′=number of atoms of renewable organic carbon, within the meaning of Standard ASTM D6866, in the monomer(s) k.

2. The copolyamide according to claim 1 , wherein:
the molar content of A is between 22 and 64%, and
the molar contents of cycloaliphatic diamine and of Cw diacid are each between 18 and 39%.

3. The copolyamide according to claim 1 , wherein the cycloaliphatic diamine is bis(3,5-dialkyl-4-aminocyclohexyl)methane, bis(3,5-dialkyl-4-aminocyclohexyl)ethane, bis(3,5-dialkyl-4-aminocyclohexyl)propane, bis(3,5-dialkyl-4-amino-cyclohexyl)butane, bis(3-methyl-4-aminocyclohexyl)methane (MACM), p-bis(aminocyclohexyl)-methane (PACM) or isopropylidenedi(cyclohexylamine) (PACP).

4. The copolyamide according to claim 1 , wherein the Cw diacid is succinic acid (w=4), adipic acid (w=6), heptanedioic acid (w=7), azelaic acid (w=9), sebacic acid (w=10), undecanedioic acid (w=11), dodecanedioic acid (w=12), brassylic acid (w=13), tetradecanedioic acid (w=14), hexadecanedioic acid (w=16), octadecanedioic acid (w=18), octadecenedioic acid (w=18), eicosanedioic acid (w=20), docosanedioic acid (w=22) or dimer fatty acids having 36 carbons.

5. The copolyamide according to claim 1 , of the formula 11/B.10, 11/P.10, 11/B.12, 12/B.12, 11/P.12, 12/P.12, 11/B.14, 11/P.14, 11/B.18 or 11/P.18 wherein B stands for BMAC and P stands for PACM.

6. The copolyamide according to claim 1 , additionally comprising at least one third unit such that the copolyamide has the formula:
A/(diamine)·(C w diacid)/(C t diamine)·(C u diacid)

in which t represents the number of carbon atoms of the diamine and u represents the number of carbon atoms of the diacid,
wherein at least one of the monomers A, the Cw diacid, the Ct diamine or the Cu diacid is obtained, in all or part, from renewable starting materials according to Standard ASTM D6866, having a content % C renew.org of greater than or equal to 54%,
and wherein the molar content of A is up to 64%, and Ct diamine is a cycloaliphatic diamine.

7. The copolyamide according to claim 6 , wherein:
the molar content of A is between 22 and 64%,
the sum of the molar contents of cycloaliphatic diamine and of Ct diamine, on the one hand, and the sum of the molar contents of Cw and Cu diacids, on the other hand, are each between 18 and 39%.

8. The copolyamide according to claim 6 , wherein the Ct diamine is a cycloaliphatic diamine that is bis(3,5-dialkyl-4-aminocyclohexyl)methane, bis(3,5-dialkyl-4-aminocyclohexyl)ethane, bis(3,5-dialkyl-4-aminocyclohexyl)propane, bis(3,5-dialkyl-4-aminocyclohexyl)butane, bis(3-methyl-4-aminocyclohexyl)methane (MACM), p-bis(aminocyclohexyl)methane (PACM) or isopropylidenedi(cyclohexylamine) (PACP).

9. The copolyamide acco

Assignees

• Arkema France

Inventors

• Saillard Benjamin
• Blondel Philippe
• Michalowicz Claire Isabelle

Classifications

• Y10T428/1352

  Polymer or resin containing [i.e., natural or synthetic] · CPC title

• C08L77/12

  Polyester-amides · CPC title

• C08L77/06

  Polyamides derived from polyamines and polycarboxylic acids (C08L77/10 takes precedence) · CPC title

• C08G69/265

  from at least two different diamines or at least two different dicarboxylic acids · CPC title

• Y10T428/139

  Open-ended, self-supporting conduit, cylinder, or tube-type article · CPC title