Process for the preparation of diamine/dicarboxylic acid salts and polyamides thereof

Patent metadata

Field	Value
Publication number	US-10233287-B2
Application number	US-201414763617-A
Country	US
Kind code	B2
Filing date	Jan 30, 2014
Priority date	Jan 31, 2013
Publication date	Mar 19, 2019
Grant date	Mar 19, 2019

Abstract

The invention relates to a process for preparing a salt from diamine and dicarboxylic acid, the process comprising contacting a diamine gas, having a gas temperature T-gas, with a dicarboxylic acid, thereby forming a reaction mixture comprising diamine/dicarboxylic acid salt, wherein the dicarboxylic acid and the reaction mixture are kept at a temperature T-mixture of at least 10° C. below the lowest of the melting temperature of the dicarboxylic acid (Tm-acid) and the melting temperature of the resulting diamine/dicarboxylic acid salt (Tm-salt). The invention also relates to a process for preparing a polyamide comprising preparing a salt from diamine and dicarboxylic acid.

First claim

The invention claimed is:

1. A process for preparing a salt from diamine and dicarboxylic acid, the process comprising contacting a diamine gas, having a gas temperature T-gas, with a dicarboxylic acid, thereby forming a reaction mixture comprising diamine/dicarboxylic acid salt, wherein the dicarboxylic acid and the reaction mixture are kept at a temperature T-mixture of at least 10° C. below the lowest of the melting temperature of the dicarboxylic acid (Tm-acid) and the melting temperature of the resulting diamine/dicarboxylic acid salt (Tm-salt).

2. The process according to claim 1 , wherein the dicarboxylic acid is provided as a powder, as granules of granulated powder or as pellets of compressed powder, or as a mixture thereof.

3. The process according to claim 1 , wherein the contacting is carried out under an absolute pressure of at most 5 bar.

4. The process according to claim 1 , wherein T-mixture is at least 20° C. below the lower of Tm-acid and Tm-salt.

5. The process according to claim 1 , wherein T-gas is at least 5° C. above T-mixture.

6. The process according to claim 1 , wherein the contacting is carried out in an agitated bed reactor.

7. The process according to claim 1 , wherein T-gas is below T-mixture plus 5° C.

8. The process according to claim 7 , wherein the contacting is carried out in a static bed reactor or a moving bed reactor.

9. The process according to claim 1 , wherein the dicarboxylic acid comprises an aliphatic dicarboxylic acid, or an aromatic dicarboxylic acid, or a mixture thereof.

10. The process according to claim 9 , wherein the dicarboxylic acid comprises at least 50 mole %, relative to the total molar amount of dicarboxylic acid, of at least one aromatic dicarboxylic acid selected from the group consisting of terephthalic acid, 2,6-naphthalene dicarboxylic acid and biphenyl-4,4′-dicarboxylic acid.

11. The process according to claim 9 , wherein the dicarboxylic acid consists of at least 95 mole % of terephthalic acid, relative to the total molar amount of dicarboxylic acid.

12. The process according to claim 10 , wherein T-mixture is kept below 210° C.

13. The process according to claim 1 , wherein the diamine is selected from the group consisting of aliphatic C2-C12 diamines, an aliphatic aromatic diamines, and mixtures thereof.

14. The process according to claim 13 , wherein the aliphatic diamine is a linear aliphatic diamine, a trans-1,4-diaminocyclohexane, or a mixture thereof.

15. A process for preparing a semi-crystalline polyamide from diamine and dicarboxylic acid comprising:
(i) contacting a diamine gas, having a gas temperature T-gas, with a dicarboxylic acid, thereby forming a reaction mixture comprising diamine/dicarboxylic acid salt (DD-salt), wherein the dicarboxylic acid and the reaction mixture are kept at a temperature T-mixture of at least 10° C. below the lowest of the melting temperature of the dicarboxylic acid (Tm-acid) and the melting temperature of the resulting diamine/ dicarboxylic acid salt (Tm-salt); and
(ii) solid-state polymerizing the DD-salt thereby obtaining the semi-crystalline polyamide.

16. The process according to claim 15 , wherein
the semi-crystalline polyamide is a semi-crystalline semi-aromatic polyamide;
the diamine comprises at 90 mole %, relative to the total molar amount of diamine, of a linear aliphatic C2-C10 diamine, an aliphatic-aromatic diamine or a mixture thereof; and
the dicarboxylic acid comprises at least 50 mole %, relative to the total molar amount of dicarboxylic acid, of at least one aromatic dicarboxylic acid selected from the group consisting of terephthalic acid, 2,6-naphthalene dicarboxylic acid, and biphenyl-4,4′-dicarboxylic acid.

17. The process according to claim 15 , wherein the solid state polymerisation is at least partly carried out at a temperature above 220° C.

18. The process according to claim 16 , wherein the dicarboxylic acid consists of at least 95 mole %, relative to the total molar amount of dicarboxylic acid, of at least one aromatic dicarboxylic acid selected from the group consisting of terephthalic acid, 2,6-naphthalene dicarboxylic acid and biphenyl-4,4′-dicarboxylic acid.

19. The process according to claim 18 , wherein step (i) is practiced by maintaining T-mixture below 210° C. and adding the diamine in an amount such that the diamine/dicarboxylic acid molar ratio in the DD-salt obtained from step (i) is in a range of 0.75-1.10.

20. The process according to claim 18 , wherein T mixture in step (i) is above 210° C.

21. The process according to claim 15 , wherein the solid-state polymerization of step (ii) is carried out in a static bed reactor, a moving bed reactor, or an agitated bed reactor.

22. The process according to claim 20 , wherein T-mixture is above 220° C.

23. The process according to claim 15 , wherein the diamine is added in such an amount that the diamine/dicarboxylic acid molar ratio in the DD-salt obtained from step (i) is in the range of 0.90-1.10.

24. The process according to claim 1 , wherein the contacting is carried out under an absolute pressure of at most 3 bar.

25. The process according to claim 1 , wherein the contacting is carried out under an absolute pressure of at most 1 bar.

Assignees

• Dsm Ip Assets Bv

Inventors

• Rulkens Rudy
• Kierkels Renier Henricus Maria
• Vanden Poel Geert Adelina Rudolf
• Cuypers Theo Joseph
• Grolman Eric

Classifications

• C07C63/28

  Salts thereof · CPC title

• C08G69/32 Primary

  from aromatic diamines and aromatic dicarboxylic acids with both amino and carboxylic groups aromatically bound · CPC title

• C08G69/26

  derived from polyamines and polycarboxylic acids · CPC title

• C08G69/28

  Preparatory processes · CPC title

• C07C209/68

  from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton · CPC title