IP Library Granted Patent US 11,932,749
Granted Patent B2
US 11,932,749 · App. 17/806,915 · Granted Mar 19, 2024

Plasticizer composition comprising tripentyl esters of 1,2,4-cyclohexanetricarboxylic acid

Inventors: Michael Grass (Haltern am See, DE); Florian Boeck (Witten, DE); Benjamin Woldt (Suedlohn, DE)
Assignee: Evonik Oxeno GmbH & Co. KG
C08K5/12C08K5/0016
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Quick Facts
Patent No.
US 11,932,749
App. No.
17/806,915
Granted
Mar 19, 2024
Kind
B2
Abstract

A plasticizer composition contains a compound according to the following formula (I) wherein the radicals R 1 , R 2 and R 3 are each independently selected from n-pentyl, 2-methylbutyl and 3-methylbutyl. The plasticizer composition can be used as plasticizer for polymers and a corresponding plastic composition contains the plasticizer composition.

Claims (29)

1. A plasticizer composition, comprising consisting of:

at least one compound according to the following formula (I)

wherein the radicals R 1 , R 2 and R 3 are each independently selected from the group consisting of n-pentyl, 2-methylbutyl, and 3-methylbutyl,

wherein the at least one compound according to the formula (I) consists of a mixture of compounds according to the formula (I),

wherein the mixture comprises one radical selected from the group consisting of n-pentyl, 2-methylbutyl, and 3-methylbutyl at a proportion of 30 to 95 mol %, and one other radical or two other radicals from the group specified at a proportion of 5 to 70 mol %, based in each case on a total amount of all radicals R 1 , R 2 and R 3 of the at least one compound according to the formula (I), and

at least one further plasticizer selected from the group consisting of alkyl benzoates, dialkyl adipates, glycerol esters, trialkyl citrates, acylated trialkyl citrates, glycol dibenzoates, trialkyl esters of trimellitic acid, dialkyl terephthalates, dialkyl phthalates, esters of furandicarboxylic acid, dialkanoyl esters of dianhydrohexitols, epoxidized fatty acid alkyl esters, polymer plasticizers, and dialkyl esters of 1,2-, 1,3- or 1,4-cyclohexanedicarboxylic acid.

2. The plasticizer composition according to claim 1 , wherein the mixture consists of one radical selected from the group consisting of n-pentyl, 2-methylbutyl, and 3-methylbutyl at a proportion of 40 to 95 mol %, and one other radical or two other radicals from the group specified at a proportion of 5 to 60 mol %, based in each case on the total amount of all radicals R 1 , R 2 and R 3 of the at least one compound according to the formula (I).

3. The plasticizer composition according to claim 1 , wherein the mixture consists of the 2-methylbutyl radical at a proportion of at maximum 60 mol %, based on the total amount of all radicals R 1 , R 2 and R 3 of the at least one compound according to the formula (I).

4. The plasticizer composition according to claim 3 , wherein the mixture consists of the 2-methylbutyl radical at a proportion of at maximum 40 mol %, based on the total amount of all radicals R 1 , R 2 and R 3 of the at least one compound according to the formula (I).

5. The plasticizer composition according to claim 1 , wherein the at least one further plasticizer is selected from the group consisting of C 8 - to C 13 -alkyl benzoates, C 4 - to C 10 -dialkyl adipates, trialkyl citrates having C 4 to C 9 -alkyl groups, C 4 - to C 10 -trialkyl trimellitates, C 4 - to C 9 -dialkyl terephthalates, C 4 - to C 13 -dialkyl phthalates, and C 4 - to C 10 -dialkyl esters of 1,2-, 1,3- or 1,4-cyclohexanedicarboxylic acid.

6. The plasticizer composition according to claim 1 , wherein the at least one further plasticizer is at least one dialkyl esters of 1,2- or 1,4-cyclohexanedicarboxylic acid.

7. The plasticizer composition according to claim 6 , wherein the at least one 1,2- or 1,4-cyclohexanedicarboxylic ester is a corresponding diisononyl or di-2-ethylhexyl ester.

8. The plasticizer composition according to claim 1 , wherein said at least one further plasticizer is a dialkyl terephthalate which is di-ethylhexyl terephthalate.

9. The plasticizer composition according to claim 1 , wherein said further plasticizer is selected from the group consisting of dibutyl terephthalate, di(iso)pentyl terephthalate, isodecyl benzoate, isononyl benzoate, acetyl tributyl citrate, tributyl citrate, dipropyleneglycol dibenzoate, diethyleneglycol dibenzoate, triethyleneglycol dibenzoate, and mixtures of two or more thereof.

10. A method of plasticizing, comprising:

mixing a polymer with the plasticizer composition according to claim 1 .

11. The method according to claim 10 , wherein the polymer is PVC or a vinyl chloride-containing polymer.

12. A plastic composition, comprising:

one or more polymers selected from the group consisting of polyvinyl chloride (PVC), copolymers of vinyl chloride with vinyl acetate or with butyl acrylate, polyalkyl methacrylate (PAMA), polyvinyl butyral (PVB), polyurethane, polysulfides, polylactic acid (PLA), polyhydroxybutyral (PHB), and nitrocellulose; and

the plasticizer composition according to claim 1 .

13. The plastic composition according to claim 12 , wherein the one or more polymers comprises at least PVC.

14. The plasticizer composition according to claim 1 , wherein the at least one further plasticizer is a dialkanoyl ester of a dianhydrohexitol which is a dialkanoyl ester of isosorbide.

15. The plasticizer composition according to claim 1 , wherein the at least one further plasticizer is a polymer plasticizer which is a polyadipate.

16. The plasticizer composition according to claim 1 , wherein the at least one further plasticizer is a dialkyl phthalate which is a C 9 - to C 13 -dialkyl phthalate.

17. A plasticizer composition comprising least one compound according to the following formula (I)

wherein the radicals R 1 , R 2 and R 3 are each independently selected from the group consisting of n-pentyl, 2-methylbutyl and 3-methylbutyl,

wherein the at least one compound according to the formula (I) comprises a mixture of compounds according to the formula (I),

wherein the mixture comprises one radical selected from the group consisting of n-pentyl, 2-methylbutyl and 3-methylbutyl at a proportion of 30 to 95 mol % and one other radical or the two other radicals from the group specified at a proportion of 5 to 70 mol %, based in each case on a total amount of all radicals R 1 , R 2 and R 3 of the at least one compound according to the formula (I), and

wherein the 2-methylbutyl radical is present in the mixture at a proportion of at maximum 60 mol % based in each case on all radicals R 1 , R 2 and R 3 of the compound according to the formula (I).

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 19, 2023
From: EVONIK OPERATIONS GMBH
To: EVONIK OXENO GMBH & CO. KG
Reel/Frame 065692/0785 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 25, 2022
From: GRASS, MICHAEL; BOECK, FLORIAN; WOLDT, BENJAMIN
To: EVONIK OPERATIONS GMBH
Reel/Frame 060606/0825 →
Priority Claims (1)
EP 21179453 · Jun 15, 2021 · regional
Continuity (1)
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