Process for preparing a diamine/dicarboxylic acid salt

Patent metadata

Field	Value
Publication number	US-9475753-B2
Application number	US-201214234248-A
Country	US
Kind code	B2
Filing date	Jul 26, 2012
Priority date	Jul 26, 2011
Publication date	Oct 25, 2016
Grant date	Oct 25, 2016

Abstract

The present invention also relates to a process for preparing a diamine/dicarboxylic acid salt wherein the dicarboxylic acid comprises an aromatic dicarboxylic acid and is provided in a powder form; the diamine is provided in a liquid form gradually dosed to the dicarboxylic acid powder, while keeping the dicarboxylic acid powder in constant movement; the processing temperature is above 0° C. and below the boiling temperature of the diamine and the melting temperature of the acid and the salt, and the reaction mixture comprises at most 5 wt. % of water. The present invention also relates to an anhydrous diamine/dicarboxylic acid salt obtainable by the process according to invention, or any embodiment thereof as described above.

First claim

The invention claimed is:

1. A process for preparing a diamine/dicarboxylic acid salt comprising the steps of:
(i) forming a reaction mixture by contacting a diamine liquid with a dicarboxylic acid powder comprising an aromatic dicarboxylic acid having a particle size distribution, measured by the method according to ISO 13320, with a d10 of at least 15 μm and a d90 of at most 1000 μm and with a median particle size (d50) in a range of 40-500 μm, and
(ii) allowing the diamine and the aromatic dicarboxylic acid in the reaction mixture to react to form a diamine/dicarboxylic acid salt, wherein
step (i) comprises the steps of:
(a) gradually dosing the diamine liquid to the aromatic dicarboxylic acid powder , while keeping the aromatic dicarboxylic acid powder in constant movement, and thereafter
(b) keeping the reaction mixture in constant movement for a time period directly following completion of the dosing; wherein
steps of (a) and (b) are carried out at a temperature above 0° C. and below all of the following: the boiling temperature of the diamine and the melting temperatures of the dicarboxylic acid, the diamine/dicarboxylic acid salt and any intermediate reaction product, and wherein
the reaction mixture in steps (a) and (b) comprises at most 5 wt. % of water, relative to the total weight of the diamine and dicarboxylic acid.

2. The process according to claim 1 , wherein the diamine and the dicarboxylic acid in the reaction mixture are present in a molar ratio of diamine over dicarboxylic acid in the range of 0.9-1.1.

3. The process according to claim 1 , wherein the dicarboxylic acid powder is a mixture of an aliphatic dicarboxylic acid and an aromatic dicarboxylic acid.

4. The process according to claim 3 , wherein the mixture of aliphatic dicarboxylic acid and aromatic dicarboxylic acid is a dry blend of solid particles of the aliphatic dicarboxylic acid and solid particles of the aromatic dicarboxylic acid.

5. The process according to claim 3 , wherein the aliphatic dicarboxylic acid and the aromatic dicarboxylic acid are present in a molar ratio between 90:10 and 10:90.

6. The process according to claim 1 , wherein the dicarboxylic acid consists of 90-100 mole % of aromatic dicarboxylic acid and 10-0 mole % of aliphatic dicarboxylic acid.

7. The process according to claim 1 , wherein the aromatic dicarboxylic acid comprises either isophthalic acid, terephthalic acid or naphthalene dicarboxylic acid, or any combination thereof.

8. The process according to claim 1 , wherein the aliphatic dicarboxylic acid comprises adipic acid and/or sebacic acid.

9. The process according to claim 1 , wherein the diamine comprises an aliphatic diamine having 4-12 carbon atoms.

10. The process according to claim 9 , wherein the diamine comprises 1,4-butane diamine and/or 1,6-hexane diamine.

11. The process according to claim 1 , wherein step (i) comprises contacting the diamine liquid and the dicarboxylic acid powder by spraying or dripping the diamine liquid onto dicarboxylic acid powder while moving the dicarboxylic acid powder.

12. The process according to claim 1 , wherein step (i) comprises contacting and mixing the diamine liquid and the dicarboxylic acid powder in a tumble mixer, a ploughshare mixer, a conical mixer, a planetary screw mixer or a fluidized bed reactor.

13. The process according to claim 1 , wherein step (i) comprises contacting the diamine liquid and the dicarboxylic acid powder at a temperature between 0° C. and the boiling temperature of water.

14. The process according to claim 1 , which further comprises the step of (iii) removing neutralization heat produced upon reaction of the diamine and the dicarboxylic acid to form the diamine/dicarboxylic acid salt via a heat exchanger.

15. The process according to claim 1 , wherein the dicarboxylic acid powder has a particle size distribution with a Span, defined by the ratio of (d84-d16)/d50, of at most 5.

16. A diamine/dicarboxylic acid salt, wherein the salt is a granulate material obtained by the process according to claim 1 .

17. The salt according to claim 16 , wherein the salt is an anhydrous salt, comprising less than 0.5 wt. % water, relative to the total weight of the salt.

18. The salt according to claim 16 , wherein the salt has a flowability defined by the ratio (ffc) of consolidation stress, σ1, to unconfined yield strength, σc, measured by the shear test method according to ASTM D6773 of at least 10.

19. The salt according to claim 16 , wherein the salt is a granulate material consisting of polycrystalline granules comprising micro-crystallites, wherein the micro-crystallites have a particle size distribution, measured by software supported analysis of SEM images taken from surface areas of granules, with a volume based d90 of at most 5 μm.

20. The salt according to claim 16 , wherein the salt is a granulate material consisting of polycrystalline granules, wherein the polycrystalline granules have a particle size distribution, measured by the method according to ISO 13320, with a d10 of at least 20 μm, a d90 of at most 1000 μm, and a median particle size (d50) in the range of 50-600 μm.

21. The salt according to claim 20 , wherein the d10 is in the range of 20-200 μm, the d50 is in the range of 50-500 μm, and the d90 is in the range of 200-1000 μm.

22. The salt according to claim 16 , wherein the polycrystalline granules have a particle size distribution with a Span, defined by the ratio of (d84-d16)/d50, of at most 5.

23. The salt according to claim 16 , wherein the granulate material has a compressibility, expressed by the ratio of (TBD-ABD)/TBD*100%, of at most 35%, wherein ABD is an aerated bulk density and TBD is a tapped bulk density both measured by the method according to ASTM D6393.

24. The salt according to claim 16 , which comprises a salt based on 1,4-butane diamine and terephthalic acid and/or a salt based on 1,6-hexane diamine and terephthalic acid.

25. The salt according to claim 22 , wherein the Span of the polycrystalline granules is at most 2.5.

26. A process for the preparation of a polyamide which comprises forming a polyamide using the salt according to claim 16 .

Assignees

• Grolman Eric
• Rulkens Rudy
• Dsm Ip Assets Bv

Inventors

• Grolman Eric
• Rulkens Rudy

Classifications

• C07C51/412

  by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part · CPC title

• C07C63/28

  Salts thereof · CPC title

• C07C63/24

  1,3 - Benzenedicarboxylic acid · CPC title

• C07C211/12

  1,6-Diaminohexanes · CPC title

• C07C211/09

  Diamines · CPC title