Aliphatic esters and polymer compositions containing them

Patent metadata

Field	Value
Publication number	US-2016333169-A1
Application number	US-201515111036-A
Country	US
Kind code	A1
Filing date	Jan 9, 2015
Priority date	Jan 13, 2014
Publication date	Nov 17, 2016
Grant date	—

Abstract

This invention relates to a family of aliphatic esters having the following general structure:
R 1 —O—C(O)—R 4 —C(O)—[—O—R 2 —O—C(O)—R 5 —C(O)—] m —O—R 3
in which:
R 1 is selected from one or more of the groups consisting of H, linear and branched saturated and unsaturated alkyl residues of the C 1 -C 24 type, and polyol residues esterified with C 1 -C 24 monocarboxylic acids; R 2 comprises —CH 2 —C(CH 3 ) 2 —CH 2 — and C 2 -C 8 alkylene groups, and comprises at least 50% in moles of the said —CH 2 —C(CH 3 ) 2 —CH 2 — groups; R 3 is selected from one or more of the groups consisting of H, linear and branched saturated and unsaturated alkyl residues of the C 1 -C 24 type, and polyol residues esterified with C 1 -C 24 monocarboxylic acids; R 4 and R 5 comprise one or more C 2 -C 22 alkylenes and comprise at least 50% in moles of C 7 alkylenes; m lies between 1 and 20;
at least one of R 1 and/or R 3 comprise polyol residues esterified with at least one C 1 -C 24 monocarboxylic acid selected from the group consisting of stearic acid, palmitic acid, 9-ketostearic acid, 10-ketostearic acid and mixtures thereof.

These esters are particularly suitable for use as plasticisers for various types of polymers such as for example vinyl polymers of the polyvinyl chloride (PVC) type, thermoplastic elastomers, and hydroxy acid polyesters, for example polyesters of lactic acid.

First claim

1 . Composition of aliphatic esters having formula:
R 1 —O—C(O)—R 4 —C(O)—[—O—R 2 —O—C(O)—R 5 —C(O)—] m —O—R 3
in which: R 1 is selected from one or more of the groups consisting of H, linear and branched saturated and unsaturated alkyl residues of the C 1 -C 24 type, and polyol residues esterified with C 1 -C 24 monocarboxylic acids; R 2 comprises —CH 2 —C(CH 3 ) 2 —CH 2 — and C 2 -C 8 alkylene groups, and comprises at least 50% by moles of the said —CH 2 —C(CH 3 ) 2 —CH 2 — groups; R 3 is selected from one or more of the groups consisting of H, linear and branched saturated and unsaturated alkyl residues of the C 1 -C 24 type, and polyol residues esterified with C 1 -C 24 monocarboxylic acids; R 4 and R 5 comprise one or more C 2 -C 22 alkylenes and comprise at least 50% in moles of C 7 alkylenes; m lies between 1 and 20; at least one of R 1 and/or R 3 comprise polyol residues esterified with at least one C 1 -C 24 monocarboxylic acid selected from the group consisting of stearic acid, palmitic acid, 9-ketostearic acid, 10-ketostearic acid and mixtures thereof.

2 . Composition of aliphatic esters according to claim 2 , in which at least one of R 1 and/or R 3 comprise ≧10% by moles, with respect to the total amount of R 1 and/or R 3 , of polyol residues esterified with at least one C 1 -C 24 monocarboxylic acid selected from the group consisting of stearic acid, palmitic acid, 9-ketostearic acid, 10-ketostearic acid and mixtures thereof.

3 . Composition of aliphatic esters according to claim 1 , in which at least one of R 1 and/or R 3 comprise polyol residues esterified with at least one C 1 -C 24 monocarboxylic acid selected from the group consisting of 9-ketostearic acid, 10-ketostearic acid and mixtures thereof.

4 . Composition of aliphatic esters according to claim 3 , in which at least one of R 1 and/or R 3 comprise ≧5% in moles, with respect to the total amount of R 1 and/or R 3 , of polyol residues esterified with at least one C 1 -C 24 monocarboxylic acid selected from the group consisting of 9-ketostearic acid, 10-ketostearic acid and mixtures thereof.

5 . Composition of aliphatic esters according to claim 1 , in which R 2 is the —CH 2 —C(CH 3 ) 2 —CH 2 — group.

6 . Composition of aliphatic esters according to claim 1 , in which R 4 and R 5 are C 7 alkylenes.

7 . Polymer compositions comprising the composition of aliphatic esters according to claim 1 .

8 . Polymer compositions according to claim 7 , comprising from 10 to 80% by weight of a plasticizer comprising the composition of aliphatic esters.

9 . Polymer compositions according to claim 7 , comprising one or more polymers selected from chlorinated vinyl polymers, thermoplastic elastomers and hydroxy acid polyesters.

10 . Use of the composition of aliphatic esters according to claim 1 as plasticisers, modifiers for polyesters and polyamides, impregnating agents for wood, and bases for thermoplastic and thermohardening polyurethanes.

11 . Composition of aliphatic esters according to claim 2 , in which at least one of R 1 and/or R 3 comprise polyol residues esterified with at least one C 1 -C 24 monocarboxylic acid selected from the group consisting of 9-ketostearic acid, 10-ketostearic acid and mixtures thereof.

12 . Composition of aliphatic esters according to claim 2 , in which R 2 is the —CH 2 —C(CH 3 ) 2 —CH 2 — group.

13 . Composition of aliphatic esters according to claim 3 , in which R 2 is the —CH 2 —C(CH 3 ) 2 —CH 2 — group.

14 . Composition of aliphatic esters according to claim 4 , in which R 2 is the —CH 2 —C(CH 3 ) 2 —CH 2 — group.

15 . Composition of aliphatic esters according to claim 2 , in which R 4 and R 5 are C 7 alkylenes.

16 . Composition of aliphatic esters according to claim 3 , in which R 4 and R 5 are C 7 alkylenes.

17 . Composition of aliphatic esters according to claim 4 , in which R 4 and R 5 are C 7 alkylenes.

18 . Composition of aliphatic esters according to claim 5 , in which R 4 and R 5 are C 7 alkylenes.

19 . Polymer compositions comprising the composition of aliphatic esters according to claim 2 .

20 . Polymer compositions comprising the composition of aliphatic esters according to claim 3 .

Assignees

• Novamont Spa

Inventors

• Bastioli Catia
• Capuzzi Luigi
• Digioia Francesca
• Marini Nicola

Classifications

• C08K5/0016

  Plasticisers · CPC title

• C08G63/16 Primary

  Dicarboxylic acids and dihydroxy compounds · CPC title

• C08J3/18

  Plasticising macromolecular compounds (plasticisers C08K) · CPC title

• C08L27/06

  Homopolymers or copolymers of vinyl chloride · CPC title

• C08L67/04

  Polyesters derived from hydroxycarboxylic acids, e.g. lactones (C08L67/06 takes precedence) · CPC title