Tripentyl esters of trimellitic acid

Patent metadata

Field	Value
Publication number	US-10875981-B2
Application number	US-201816029413-A
Country	US
Kind code	B2
Filing date	Jul 6, 2018
Priority date	Sep 28, 2015
Publication date	Dec 29, 2020
Grant date	Dec 29, 2020

Abstract

An ester mixture of trialkyl esters of cyclohexane-1,2,4-tricarboxylates having isomeric pentyl radicals in which more than 5 mol % of the isomeric pentyl radicals are branched.

First claim

The invention claimed is:

1. A composition, comprising:
an ester mixture of trialkyl esters of cyclohexane-1,2,4-tricarboxylates having isomeric pentyl radicals,
wherein more than 5 mol % of the isomeric pentyl radicals are branched,
wherein at least 50 mol % of the branched isomeric pentyl radicals are 2-methylbutyl radicals, and
wherein more than 10 mol % of the isomeric pentyl radicals are linear.

2. The composition according to claim 1 , wherein at least 15 mol % of the isomeric pentyl radicals are branched, and
wherein more than 10 mol % and less than 50 mol % of the isomeric pentyl radicals are linear.

3. The composition according to claim 1 , wherein at least 70 mol % of the branched isomeric pentyl radicals are 2-methylbutyl radicals.

4. The composition according to claim 1 , wherein more than 10 mol % and less than 30 mol % of the isomeric pentyl radicals are linear.

5. The composition of claim 1 , wherein the trialkyl esters contain at least 75 mol % branched 2-methylbutyl radicals, and
wherein a molar ratio of 2-methylbutyl radicals to linear pentyl radicals is in a range of 10:90 to 75:25.

6. The composition of claim 5 , wherein the molar ratio of 2-methylbutyl radicals to linear pentyl radicals is in a range of 30:70 to 70:30.

7. The composition of claim 1 , wherein at least 90 mol % of the branched isomeric pentyl radicals are 2-methylbutyl radicals.

8. The composition of claim 1 , wherein at least 40 mol % to 50 mol % of the branched isomeric pentyl radicals are 3-methylbutyl radicals.

9. A process for preparing the composition of claim 1 , the process comprising:
reacting trimellitic acid, a trimellitic acid derivative, or both, with a mixture of isomeric pentanols to obtain trialkyl esters of trimellitic acid,
wherein of the mixture of isomeric pentanols:
more than 5 mol % of the isomeric pentyl radicals are branched isomeric pentyl radicals,
at least 50 mol % of the branched isomeric pentyl radicals are 2-methylbutyl radicals, and
more than 10 mol % of the isomeric pentyl radicals are linear;

and
hydrogenating the trialkyl esters of trimellitic acid to obtain the ester mixture of trialkyl esters of cyclohexane-1,2,4-tricarboxylates having isomeric pentyl radicals.

10. The process according to claim 9 , wherein, during the reaction of the trimellitic acid, the trimellitic acid derivative, or both with the mixture of isomeric pentanols, the reaction mixture is heated to boiling, and after attaining boiling temperature, adding at least 0.2 molar equivalent of the amount of the mixture of isomeric pentanols needed to introduce all the isomeric pentyl radicals incorporated in the ester mixture to the reaction mixture containing the trimellitic acid, the trimellitic acid derivative, or both.

11. A plasticizer, comprising the composition of claim 1 .

12. A plasticizer composition, comprising the composition of claim 1 and a further polymer-plasticizing compound.

13. A composition, comprising the plasticizer of claim 11 , said composition being selected from the group consisting of an adhesive, a sealing compound, a coating material, a paint, an ink and a plastisol.

14. The plasticizer composition of claim 12 , wherein the further polymer-plasticizing compound comprises at least one selected from the group consisting of alkyl benzoates, dialkyl adipates, glycerol esters, trialkyl citrates, acylated trialkyl citrates, glycol dibenzoates, trimellitates with radicals other than those described in the present invention, dialkyl terephthalates, dialkyl phthalates, esters of furandicarboxylic acid, dialkanoyl esters of dianhydrohexitols, epoxidized fatty acid alkyl esters, polymer plasticizers, polyadipates, dialkyl esters of cyclohexane-1,2-dicarboxylic acid, dialkyl esters of cyclohexane-1,3-dicarboxylic acid, and dialkyl esters of cyclohexane-1,4-dicarboxylic acid.

15. A polymer composition, comprising the plasticizer composition according to claim 14 and at least one polymer selected from the group consisting of polyvinyl chloride, copolymers of vinyl chloride with vinyl acetate, copolymers of vinyl chloride with butyl acrylate, polyalkyl methacrylate (PAMA), polyvinyl butyral (PVB), chlorosulphonated polyethylene, polyurethane, polysulphides, polylactic acid (PLA), polyhydroxybutyral (PHB) and nitrocellulose.

16. An article, comprising the plasticizer of claim 11 , said article being selected from the group consisting of a foam, a synthetic leather, a floorcovering, a wallcovering, a roofing membrane, an underbody protection, a fabric coating, a cable, a wire insulation, a hose, a tube, an extruded article, a film, a toy, a contact sheet, a food packaging and a medical article.

17. An article, comprising the plasticizer of claim 11 , said article being selected from the group consisting of a top layer of a floorcovering, a film in the automobile interior sector, a tube of a medical article and a blood bag.

Assignees

• Evonik Operations Gmbh

Inventors

• Woldt Benjamin
• Grass Michael
• Boeck Florian

Classifications

• C08L27/06

  Homopolymers or copolymers of vinyl chloride · CPC title

• C08K5/11

  of acyclic polycarboxylic acids · CPC title

• C08K5/0016 Primary

  Plasticisers · CPC title

• C07C69/76

  Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring · CPC title

• C07C67/12

  from asymmetrical anhydrides · CPC title