MIXTURE OF DIESTERS OF DIANHYDROHEXITOL DERIVATIVES WITH CARBOXYLIC ACIDS OF THE EMPIRICAL FORMULA C8H17COOH, PROCESS FOR PREPARING THESE DIESTERS, AND USE OF THESE MIXTURES

• US 20090301348A1
• Filed: 12/21/2007
• Published: 12/10/2009
• Est. Priority Date: 02/05/2007
• Status: Active Grant

• Current Assignee: Evonik Degussa GmbH
• Original Assignee: Evonik Oxeno GmbH (Rag-Stiftung)
• Inventors: Scholz, Norbert, Bueschken, Wilfried, Kaizik, Alfred, Lueken, Hans-Gerd, Grass, Michael
• Granted Patent: US 8,258,325 B2
• Time in Patent Office: Days
• US Class Current: 106/287.200
• CPC Class Codes: C07D 493/04 Ortho-condensed systems
• CPC Class Codes: C08K 5/1535 Five-membered rings
• CPC Class Codes: C08L 27/06 Homopolymers or copolymers of vinyl chloride

Abstract

The present invention relates to a mixture comprising diesters of the formula (I) where R¹ to R⁸═H or alkyl group having from 1 to 6 carbon atoms, where the R¹ to R⁸ radicals may be the same or different, which is characterized in that at least two different diesters I are present in the mixture, said diesters differing in the structure of at least one of the carboxylic acid radicals C⁸H¹⁷COO present, to a process for preparing diesters of an isosorbide derivative of the formula I, in which a hexahydric alcohol and/or a monoanhydro or dianhydro derivative of the alcohol is esterified with a mixture of at least two different carboxylic acids of the empirical formula C⁸H¹⁷COOH, and to the use of these mixtures in paints, inks or coatings, in plastisols, adhesives or adhesive components, in sealants, as plasticizers in polymers or polymer components, as solvents, as lubricant oil components and as assistants in metal processing, and also PVC compositions or plastisols comprising PVC and from 5 to 250 parts by mass of the mixture per 100 parts by mass of PVC.

Claims

1. A mixture, comprising diesters of the formula I composed of a dianhydrohexitol derivative with carboxylic acids of the empirical formula C₈H₁₇COOH

2. The mixture according to claim 1, wherein

the carboxylic acid mixture obtained via hydrolysis of the diesters present in the mixture comprises at least two carboxylic acids of the empirical formula C₈H₁₇COOH with a different constitutional formula, the proportion present of any of the carboxylic acids present in the mixture not being more than 95 mol % in the carboxylic acid mixture.

3. The mixture according to claim 1,

wherein

the carboxylic acids of the empirical formula C₈H₁₇COOH obtained via hydrolysis of the diesters present in the mixture comprise less than 10 mol % of 3,5,5-trimethylhexanoic acid.

4. The mixture according to claim 1,

wherein

the carboxylic acid radicals C₈H₁₇COO of the diesters present in the mixture have a degree of branching of from 0.7 to 2.0.

5. The mixture according to claim 1,

wherein

the carboxylic acid radicals C₈H₁₇COO of the diesters present in the mixture have a degree of branching of from 1.2 to 1.9.

6. The mixture according to claim 1,

wherein

each of the radicals R¹ to R⁸ is H.

7. The mixture according to claim 1,

wherein

the diesters of the mixture comprise at least two different bicyclic substructures of formula I, which differ via their configuration.

8. The mixture according to claim 1,

wherein

the diesters of the mixture comprise at least two diesters with different molar masses.

9. The mixture according to claim 1,

wherein

the mixture can comprise not only diesters of different molar mass but also diester isomers having a different configuration of the bicyclic substructure.

10. The mixture according to claim 1,

wherein

the mixture comprises exclusively diesters all comprising the same bicyclic substructure of formula I, and the individual diester isomers differ only via differently structured carboxylic acid radicals.

11. The mixture according to claim 1,

wherein

the diesters of the formula I are in essence diesters of the formula Ia

12. The mixture according to claim 10,

wherein

the diesters are in essence diesters of isosorbide.

13. The mixture according to claim 1,

wherein

it comprises at least one polymer and/or at least one further plasticizer which is not a diester of the formula I.

14. The mixture according to claim 13,

wherein

the ratio by weight of polymer to diesters of the formula I is from 30:

1 to 1;

2.5.

15. The mixture according to claim 13,

wherein

the molar ratio of further plasticizer to the diesters of the formula I is from 1:

10 to 10;

1.

16. The mixture according to claim 13,

wherein

the polymer is PVC.

28. A paint, an ink or a coating, a plastisol, an adhesive or a component of an adhesive, a sealing composition, a plasticizer in a plastic or in a component of a plastic, a solvent, a component of a lubricating oil or an auxiliary during metalworking comprising a mixture according to claim 1.

29. The product according to claim 28,

wherein

the plastic is PVC.

30. The product according to claim 28,

wherein

the plastisol is a PVC plastisol.

31. A PVC composition, comprising PVC and from 5 to 250 parts by weight of a mixture according to claim 1 per 100 parts by weight of PVC.

32. A plastisol, comprising PVC and from 5 to 250 parts by weight of a mixture according to claim 1 per 100 parts by weight of PVC.

17. A process for preparation of diesters of the formula I

18. The process according to claim 17,

wherein

a mixture of isomeric carboxylic acids of the empirical formula C₈H₁₇COOH is used whose average degree of branching is from 0.7 to 2.0.

19. The process according to claim 17,

wherein,

using an alcohol of the formula II or the monoanhydro derivative of the alcohol, the dehydration reaction is carried out separately prior to the esterification reaction.

20. The process according to claim 17,

wherein,

using an alcohol of the formula II or the monoanhydro derivative of the alcohol, the dehydration reaction and the esterification reaction are carried out in one operation.

21. The process according to claim 17,

wherein

the dehydration reaction is carried out at a temperature of from 100 to 180°

C.

22. The process according to claim 17,

wherein

the dehydration reaction is carried out in the presence of a catalyst which is identical with that used in the esterification reaction.

23. The process according to claim 17,

wherein

the esterification reaction is carried out on an acidic ion-exchanger resin.

24. The process according to claim 17,

wherein

water formed during the process is removed from the reaction mixture via passage of an inert gas through the reaction mixture.

25. The process according to claim 17,

wherein

water formed during the process is removed from the reaction mixture via distillation.

26. The process according to claim 17,

wherein

the esterification reaction is carried out at a temperature of from 120 to 260°

C.

27. The process according to claim 17,

wherein

the esterification reaction is carried out at a temperature of from 130 to 180°

C., if a separate dehydration step has been carried out previously.