IP Library Granted Patent US 11,623,912
Granted Patent B2
US 11,623,912 · App. 17/113,449 · Granted Apr 11, 2023

Triesters of cyclohexanetripropionic acid

Inventors: Imke Schulz (Lüdinghausen, DE); Michael Grass (Haltern am See, DE); Robert Franke (Marl, DE); Johannes Kraft (Marl, DE); Matthias Beller (Ostseebad Nienhagen, DE); Ralf Jackstell (Rostock, DE)
Assignee: Evonik Operations GmbH
C07C69/753C07C67/38C08F14/06C08K5/12
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Quick Facts
Patent No.
US 11,623,912
App. No.
17/113,449
Granted
Apr 11, 2023
Kind
B2
Abstract

The invention relates to triesters of cyclohexanetripropionic acid, preparation thereof and use thereof as plasticizers for polymers wherein examples of the triester of cyclohexanetripropionic acid include tri( n butyl) cyclohexane-1,2,4-tripropionate, tri(methylpropyl) cyclohexane-1,2,4-tripropionate, tri( n pentyl) cyclohexane-1,2,4-tripropionate, tri( iso pentyl) cyclohexane-1,2,4-tripropionate, tri(2-methylbutyl) cyclohexane-1,2,4-tripropionate, tri(3-methylbutyl) cyclohexane-1,2,4-tripropionate, tri( n hexyl) cyclohexane-1,2,4-tripropionate, tri( iso hexyl) cyclohexane-1,2,4-tripropionate, tri( n heptyl) cyclohexane-1,2,4-tripropionate, tri( iso heptyl) cyclohexane-1,2,4-tripropionate, tri( n octyl) cyclohexane-1,2,4-tripropionate, tri( iso octyl) cyclohexane-1,2,4-tripropionate, tri(2-ethylhexyl) cyclohexane-1,2,4-tripropionate, tri( n nonyl) cyclohexane-1,2,4-tripropionate, tri( iso nonyl) cyclohexane-1,2,4-tripropionate, tri( n decyl) cyclohexane-1,2,4-tripropionate, tri( iso decyl) cyclohexane-1,2,4-tripropionate, and tri(2-propylheptyl) cyclohexane-1,2,4-tripropionate.

Claims (20)

1. A composition comprising

a triester of cyclohexanetripropionic acid wherein the ester comprises a propionic acid moiety and an alcohol moiety wherein the three alcohol moieties of the three ester groups each 5 to 12 carbon atoms, wherein the alcohol moieties have identical carbon atom number within one molecule: and

one or more polymers.

2. The composition according to claim 1 , wherein the triester of cyclohexanetripropionic acid is a triester of cyclohexane-1,2,4-tripropionic acid or a triester of cyclohexane-1,3,5-tripropionic acid, and wherein the three alcohol moieties of the three ester groups each comprise 7 to 12 carbon atoms.

3. The composition according to claim 1 , wherein the alcohol moieties, besides the oxygen of the ester function, do not comprise any other heteroatoms, and contain no multiple bonds.

4. The composition according to claim 1 , wherein all alcohol moieties present in one molecule have identical empirical formulae and at the same time identical or different structural formulae.

5. The composition according to claim 2 , wherein the triester of cyclohexanetripropionic acid is selected from the group consisting of:

tri( n pentyl) cyclohexane-1,2,4-tripropionate, tri( iso pentyl) cyclohexane-1,2,4-tripropionate, tri(2-methylbutyl) cyclohexane-1,2,4-tripropionate, tri(3-methylbutyl) cyclohexane-1,2,4-tripropionate, tri( n hexyl) cyclohexane-1,2,4-tripropionate, tri( iso hexyl) cyclohexane-1,2,4-tripropionate, tri( n heptyl) cyclohexane-1,2,4-tripropionate, tri( iso heptyl) cyclohexane-1,2,4-tripropionate, tri( n octyl) cyclohexane-1,2,4-tripropionate, tri( iso octyl) cyclohexane-1,2,4-tripropionate, tri(2-ethylhexyl) cyclohexane-1,2,4-tripropionate, tri( n nonyl) cyclohexane-1,2,4-tripropionate, tri( iso nonyl) cyclohexane-1,2,4-tripropionate, tri( n decyl) cyclohexane-1,2,4-tripropionate, tri( iso decyl) cyclohexane-1,2,4-tripropionate, tri(2-propylheptyl) cyclohexane-1,2,4-tripropionate,

tri( n pentyl) cyclohexane-1,3,5-tripropionate, tri( iso pentyl) cyclohexane-1,3,5-tripropionate, tri(2-methylbutyl) cyclohexane-1,3,5-tripropionate, tri(3-methylbutyl) cyclohexane-1,3,5-tripropionate, tri( n hexyl) cyclohexane-1,3,5-tripropionate, tri( iso hexyl) cyclohexane-1,3,5-tripropionate, tri( n heptyl) cyclohexane-1,3,5-tripropionate, tri( iso heptyl) cyclohexane-1,3,5-tripropionate, tri( n octyl) cyclohexane-1,3,5-tripropionate, tri( iso octyl) cyclohexane-1,3,5-tripropionate, tri(2-ethylhexyl) cyclohexane-1,3,5-tripropionate, tri( n nonyl) cyclohexane-1,3,5-tripropionate, tri( iso nonyl) cyclohexane-1,3,5-tripropionate, tri( n decyl) cyclohexane-1,3,5-tripropionate, tri( iso decyl) cyclohexane-1,3,5-tripropionate and tri(2-propylheptyl) cyclohexane-1,3,5-tripropionate.

6. The composition according to claim 1 , wherein at least one polymer is selected from the group consisting of polyvinyl chloride, polyalkyl methacrylate (PAMA), polyvinyl butyral (PVB), polyurethane, polysulfide, polylactic acid (PLA), polyhydroxybutyral (PHB), nitrocellulose and copolymers of vinyl chloride with vinyl acetate or with butyl acrylate.

7. The composition according to claim 1 , wherein said composition is a constituent of an adhesive, of a sealing compound, of a coating composition, of a lacquer, of a paint, of a plastisol, of a dryblend, of a foam, of a synthetic leather, of a floor covering, the top layer or foam layer thereof, of a roofing membrane, of an underbody protection, of a fabric coating, of a cable, of a wire insulation, of a hose, of an extruded article, of a film, of an article in the automotive interior sector, of a wallpaper, of an ink, of a toy, of a contact sheet, of a food packaging or of a medical article.

8. The composition according to claim 2 , wherein the alcohol moieties, besides the oxygen of the ester function, do not comprise any other heteroatoms, and contain no multiple bonds.

9. The composition according to claim 2 , wherein all alcohol moieties present in one molecule have identical empirical formulae and at the same time identical or different structural formulae.

10. The composition according to claim 1 , wherein the triester of cyclohexanetripropionic acid is a triester of cyclohexane-1,2,4-tripropionic acid or a triester of cyclohexane-1,3,5-tripropionic acid.

11. The composition according to claim 1 , further comprising a mixture of at least two triesters of cyclohexanetripropionic acid.

12. The composition according to claim 11 , wherein all alcohol moieties present in one molecule have identical empirical formulae and at the same time identical or different structural formulae.

13. The composition according to claim 11 , wherein the alcohol moieties, besides the oxygen of the ester function, do not comprise any other heteroatoms, and contain no multiple bonds.

14. The composition according to claim 6 , wherein the triester of cyclohexanetripropionic acid is selected from the group consisting of:

tri( n pentyl) cyclohexane-1,2,4-tripropionate, tri( iso pentyl) cyclohexane-1,2,4-tripropionate, tri(2-methylbutyl) cyclohexane-1,2,4-tripropionate, tri(3-methylbutyl) cyclohexane-1,2,4-tripropionate, tri( n hexyl) cyclohexane-1,2,4-tripropionate, tri( iso hexyl) cyclohexane-1,2,4-tripropionate, tri( n heptyl) cyclohexane-1,2,4-tripropionate, tri( iso heptyl) cyclohexane-1,2,4-tripropionate, tri( n octyl) cyclohexane-1,2,4-tripropionate, tri( iso octyl) cyclohexane-1,2,4-tripropionate, tri(2-ethylhexyl) cyclohexane-1,2,4-tripropionate, tri( n nonyl) cyclohexane-1,2,4-tripropionate, tri( iso nonyl) cyclohexane-1,2,4-tripropionate, tri( n decyl) cyclohexane-1,2,4-tripropionate, tri( iso decyl) cyclohexane-1,2,4-tripropionate, tri(2-propylheptyl) cyclohexane-1,2,4-tripropionate,

tri( n pentyl) cyclohexane-1,3,5-tripropionate, tri( iso pentyl) cyclohexane-1,3,5-tripropionate, tri(2-methylbutyl) cyclohexane-1,3,5-tripropionate, tri(3-methylbutyl) cyclohexane-1,3,5-tripropionate, tri( n hexyl) cyclohexane-1,3,5-tripropionate, tri( iso hexyl) cyclohexane-1,3,5-tripropionate, tri( n heptyl) cyclohexane-1,3,5-tripropionate, tri( iso heptyl) cyclohexane-1,3,5-tripropionate, tri( n octyl) cyclohexane-1,3,5-tripropionate, tri( iso octyl) cyclohexane-1,3,5-tripropionate, tri(2-ethylhexyl) cyclohexane-1,3,5-tripropionate, tri( n nonyl) cyclohexane-1,3,5-tripropionate, tri( iso nonyl) cyclohexane-1,3,5-tripropionate, tri( n decyl) cyclohexane-1,3,5-tripropionate, tri( iso decyl) cyclohexane-1,3,5-tripropionate and tri(2-propylheptyl) cyclohexane-1,3,5-tripropionate.

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 Sep 24, 2021
From: SCHULZ, IMKE; GRASS, MICHAEL; FRANKE, ROBERT; KRAFT, JOHANNES; BELLER, MATTHIAS; JACKSTELL, RALF
To: EVONIK OPERATIONS GMBH
Reel/Frame 057588/0422 →
Priority Claims (1)
EP 19216888 · Dec 17, 2019 · regional
Continuity (1)
Related Publication 20210179534A1 · Jun 17, 2021