IP Library Granted Patent US 10,577,479
Granted Patent B2
US 10,577,479 · App. 15/278,838 · Granted Mar 3, 2020

Tripentyl esters of trimellitic acid

Inventors: Benjamin Woldt (Bochum, DE); Michael Grass (Haltern am See, DE); Florian Boeck (Muenster, DE)
Assignee: Evonik Degussa GmbH
C08K5/12C07C67/08C07C67/12C07C69/76C08K5/0016
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Quick Facts
Patent No.
US 10,577,479
App. No.
15/278,838
Granted
Mar 3, 2020
Kind
B2
Abstract

Tripentyl esters of trimellitic acid, especially mixtures of triisopentyl esters of trimellitic acid comprising isomeric pentyl radicals in which more than 5 mol % of the isomeric pentyl radicals incorporated in the ester mixture are branched, have good compatibility with PVC and PVC-containing polymers and simultaneously exhibit a lesser tendency to migrate.

Claims (18)

1. A composition, comprising:

trialkyl esters of trimellitic acid;

wherein the trialkyl radicals of the trialkyl esters are a mixture of isomeric pentyl radicals, wherein more than 5 mol % of the isomeric pentyl radicals are branched, and

at least 50 mol % of the branched isomeric pentyl radicals are 2-methylbutyl radicals.

2. The composition according to claim 1 , wherein at least 15 mol %, of the isomeric pentyl radicals of the trialkyl ester groups are branched.

3. The composition according to claim 1 , wherein more than 10 mol % and less than 95 mol % of the isomeric pentyl radicals are linear.

4. A process for preparing the composition according to claim 1 , comprising:

reacting trimellitic acid and/or a trimellitic acid derivative with a mixture of isomeric pentanols;

wherein more than 5 mol % of the isomeric pentyl radicals in the mixture of isomeric pentanols are branched isomeric pentyl radicals, and

at least 50 mol % of the branched isomeric pentyl radicals are 2-methylbutyl radicals.

5. The process according to claim 4 , wherein, during the reacting, the reaction mixture containing the trimellitic acid and/or the trimellitic acid derivative is heated to boiling and, after attaining boiling temperature, adding at least 0.2 molar equivalent of the amount of mixture of isomeric pentanols needed to introduce all the isomeric pentyl radicals incorporated in the ester mixture.

6. The process according to claim 4 , wherein

at least one isomerically pure tripentyl ester of trimellitic acid and at least one mixture of triisopentyl esters of trimellitic acid comprising isomeric pentyl radicals are mixed with one another, such that more than 5 mol % of the isomeric pentyl radicals are branched, and at least 50 mol % of the branched isomeric pentyl radicals are 2-methylbutyl radicals.

7. A plasticizer, or a plasticizer composition comprising the composition according to claim 1 and at least one further polymer-plasticizing compound.

8. A plasticizer composition comprising the composition according to claim 1 and at least one further polymer-plasticizing compound selected from the group consisting of alkyl benzoates, dialkyl adipates, glycerol esters, trialkyl citrates, acylated trialkyl citrates, glycol dibenzoates, trimellitates having radicals different from the isomeric pentyl radicals of claim 1 , dialkyl terephthalates, dialkyl phthalates, esters of furandicarboxylic acid, dialkanoyl esters of dianhydrohexitols, epoxidized fatty acid alkyl esters, polyadipates, and dialkyl esters of cyclohexane-1,2-, -1,3- or -1,4-dicarboxylic acid.

9. A polymer composition comprising the composition according to claim 1 wherein the polymer composition comprises one or more polymers selected from the group consisting of polyvinyl chloride, copolymers of vinyl chloride with vinyl acetate or with butyl acrylate, polyalkyl methacrylate (PAMA), polyvinyl butyral (PVB), chlorosulphonated polyethylene, polyurethane, polysulphides, polylactic acid (PLA), polyhydroxybutyral (PHB) and nitrocellulose.

10. A polyvinyl chloride polymer (PVC) or a PVC copolymer comprising the composition of claim 1 .

11. A plasticized product comprising the composition of claim 1 , wherein the product is selected from the group consisting of adhesives, sealing compounds, coating materials, paints, inks, plastisols, foams, synthetic leather, floor coverings, roofing membranes, underbody protection, fabric coatings, cables, wire insulation, hoses, extruded articles, films, automotive interior, wall coverings, liquid inks, toys, contact sheets, food packaging or medical articles.

Assignments (3)
CONFIRMATORY ASSIGNMENT Recorded Nov 6, 2023
From: EVONIK OPERATIONS GMBH
To: EVONIK OXENO GMBH & CO. KG
Reel/Frame 065463/0144 →
CHANGE OF NAME Recorded Jan 31, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051765/0166 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2017
From: WOLDT, BENJAMIN; GRASS, MICHAEL; BOECK, FLORIAN
To: EVONIK DEGUSSA GMBH
Reel/Frame 041093/0546 →
Priority Claims (1)
EP 15187128 · Sep 28, 2015 · regional
Continuity (1)
Related Publication 20170088691A1 · Mar 30, 2017