IP Library Granted Patent US 10,787,414
Granted Patent B2
US 10,787,414 · App. 15/867,020 · Granted Sep 29, 2020

Diisopentyl terephthalate

Inventors: Florian Boeck (Münster, DE); Michael Grass (Haltern am See, DE); Benjamin Woldt (Bochum, DE); André Huber (Marl, DE); Christine Blex (Marl, DE); Ulrike Blumenthal (Marl, DE)
Assignee: Evonik Operations GmbH
C07C69/82C07C67/02C07C67/08C08K5/12C07C2601/16
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Quick Facts
Patent No.
US 10,787,414
App. No.
15/867,020
Granted
Sep 29, 2020
Kind
B2
Abstract

A mixture of isomeric dipentyl terephthalates, pentyl radicals of which are n-pentyl radicals to an extent of less than 60 mol %, characterized by a low viscosity which does not increase significantly even at temperatures below 40° C. Plastisols comprising these mixtures have a low plastisol viscosity which moreover increases only to a minor degree with time.

Claims (19)

1. A mixture comprising diisopentyl terephthalate and a plasticizer, wherein the diisopentyl terephthalate comprises pentyl radicals of which, from more than 25 mol % to less than 60 mol % of the pentyl radicals are n-pentyl radicals, wherein the diisopentyl terephthalate comprises branched isomeric pentyl radicals wherein at least 60 mol % of the branched isomeric pentyl radicals are 2-methylbutyl radicals, and the plasticizer selected is from the group consisting of alkyl benzoates, dialkyl adipates, glycerol esters, trialkyl citrates, acylated trialkyl citrates, trialkyl trimellitates, glycol dibenzoates, esters of furandicarboxylic acid, dialkanoyl esters of dianhydrohexitols and dialkester of 1,2-, 1,3- or 1,4-cyclohexane dicarboxylic acid, wherein the mixture has a viscosity of less than 1000 Pa·s at temperatures above 10° C., and wherein the ratio of the diisopentyl terephthalate to the plasticizer is from 60:40 to 10:90.

2. The mixture according to claim 1 , comprising 2-methylbutyl radicals based on the pentyl radicals and comprising pentyl radicals of which, from more than 35 mol % to less than 50 mol % of the pentyl radicals are n-pentyl radicals, and has a Boeck factor is less than 90, and the ratio of diisopentyl terephthalate to the plasticizer is from 50:50 to 20:80.

3. The mixture according to claim 1 , wherein at least 95 mol % of the branched isomeric pentyl radicals incorporated in the ester mixture are 2-methylbutyl radicals and has a Boeck factor is less than 10 and wherein the ratio of diisopentyl terephthalate to the plasticizer is from 40:60 to 25:75.

4. The mixture according to claim 1 , wherein the mixture has a viscosity of less than 500 Pa·s at temperatures above −5° C.

5. A plastisol comprising the mixture according to claim 1 .

6. A product, in particular an underbody protection, a wall covering, an artificial leather, a fabric coating or a floor, comprising the mixture according to claim 1 .

7. A polymer composition comprising the mixture according to claim 1 as plasticizers in polymer compositions, particularly in PVC-containing polymer compositions.

8. A viscosity modifier comprising the mixture according to claim 1 wherein the viscosity modifier lowers the viscosity and improves the storage stability of a plastisol.

9. A process for making a plastisol comprising the step of adding the mixture according to claim 1 to a polymer at ambient temperatures of 20° C.

10. The method for preparing the mixture according to claim 1 comprising the step of esterifying terephthalic acid or transesterifying a terephthalic ester with a mixture of isomeric pentanols.

11. A product selected from the group consisting of an underbody protection, a wall covering, an artificial leather, a fabric coating and a floor, comprising the mixture of claim 1 .

12. A product selected from the group consisting of an underbody protection, a wall covering, an artificial leather, a fabric coating and a floor, comprising the plastisol of claim 5 .

13. A polyvinyl chloride polymer comprising the mixture according to claim 1 .

14. A plasticizer comprising the mixture according to claim 1 .

15. A method for preparing the mixture according to claim 2 comprising the step of esterifying terephthalic acid or transesterifying a terephthalic ester with a mixture of isomeric pentanols.

16. A method for preparing the mixture according to claim 3 comprising the step of esterifying terephthalic acid or transesterifying a terephthalic ester with a mixture of isomeric pentanols.

17. A method for preparing the mixture according to claim 4 comprising the step of esterifying terephthalic acid or transesterifying a terephthalic ester with a mixture of isomeric pentanols.

18. The mixture according to claim 2 , wherein at least 95 mol % of the branched isomeric pentyl radicals incorporated in the ester mixture are 2-methylbutyl radicals.

19. The mixture according to claim 3 , wherein it has a viscosity of less than 1000 Pa·s at temperatures above −5° C.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 19, 2023
From: EVONIK OPERATIONS GMBH
To: EVONIK OXENO GMBH & CO. KG
Reel/Frame 065692/0785 →
CHANGE OF NAME Recorded Dec 27, 2019
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051428/0710 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 13, 2018
From: BOECK, FLORIAN; GRASS, MICHAEL; WOLDT, BENJAMIN; HUBER, ANDRÉ; BLEX, CHRISTINE; BLUMENTHAL, ULRIKE
To: EVONIK DEGUSSA GMBH
Reel/Frame 045181/0745 →
Priority Claims (1)
EP 17152394 · Jan 20, 2017 · regional
Continuity (1)
Related Publication 20180208541A1 · Jul 26, 2018
Cited By (2)
US 12,269,916 US 12,421,415