Polymer compositions containing aliphatic esters as plasticisers

Patent metadata

Field	Value
Publication number	US-10844193-B2
Application number	US-201515111053-A
Country	US
Kind code	B2
Filing date	Jan 9, 2015
Priority date	Jan 13, 2014
Publication date	Nov 24, 2020
Grant date	Nov 24, 2020

Abstract

Disclosed is the use of a composition of aliphatic esters having the following general 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% 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; and m lies between 1 and 20, as plasticizers for polymer compositions, for example, vinyl polymers of the polyvinyl chloride (PVC) type, thermoplastic elastomers, and hydroxy acid polyesters, for example polyesters of lactic acid.

First claim

The invention claimed is:

1. A polymer composition comprising at least one thermoplastic polymer, and at least one plasticizer comprising a composition of one or more aliphatic esters having general 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 24 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% by moles of C 7 alkylenes;
m lies between 1 and 20;
wherein R 1 is different from R 3 if R 1 is H;
and wherein at least one of the R 1 and/or R 3 is present in an amount of ≥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 of stearic acid, palmitic acid, 9-ketostearic acid, 10-ketostearic acid and mixtures thereof.

2. The polymer composition according to claim 1 , in which R 1 is H and R 3 is different from R 1 .

3. The polymer composition according to claim 2 , in which R 4 and R 5 are C 7 alkylenes.

4. The polymer composition according to claim 2 , comprising from 10 to 80% by weight of the said aliphatic esters.

5. The polymer composition according to claim 2 , in which said one or more thermoplastic polymers are selected from chlorinated vinyl polymers, thermoplastic elastomers and hydroxy acid polyesters.

6. The polymer composition according to claim 2 , in which R 2 is the —CH 2 —C(CH 3 ) 2 —CH 2 —group.

7. The polymer composition according to claim 6 , in which R 4 and R 5 are C 7 alkylenes.

8. The polymer composition according to claim 7 , comprising from 10 to 80% by weight of the said aliphatic esters.

9. The polymer composition according to claim 6 , comprising from 10 to 80% by weight of the said aliphatic esters.

10. The polymer composition according to claim 1 , in which R 2 is the —CH 2 —C(CH 3 ) 2 —CH 2 —group.

11. The polymer composition according to claim 10 , in which R 4 and R 5 are C 7 alkylenes.

12. The polymer composition according to claim 10 , comprising from 10 to 80% by weight of the said aliphatic esters.

13. The polymer composition according to claim 10 , in which said one or more thermoplastic polymers are selected from chlorinated vinyl polymers, thermoplastic elastomers and hydroxy acid polyesters.

14. The polymer composition according to claim 1 , in which R 4 and R 5 are C 7 alkylenes.

15. The polymer composition according to claim 14 , comprising from 10 to 80% by weight of the said aliphatic esters.

16. The polymer composition according to claim 14 , in which said one or more thermoplastic polymers are selected from chlorinated vinyl polymers, thermoplastic elastomers and hydroxy acid polyesters.

17. The polymer composition according to claim 1 , comprising from 10 to 80% by weight of the said aliphatic esters.

18. The polymer composition according to claim 17 , in which said one or more thermoplastic polymers are selected from chlorinated vinyl polymers, thermoplastic elastomers and hydroxy acid polyesters.

19. The polymer composition according to claim 1 , in which said one or more thermoplastic polymers are selected from chlorinated vinyl polymers, thermoplastic elastomers and hydroxy acid polyesters.

20. A method for plasticizing a thermoplastic polymer composition which comprises incorporating in the thermoplastic polymer composition an aliphatic ester having general 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 24 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% by moles of C 7 alkylenes;

m lies between 1 and 20;
wherein R 1 is different from R 3 if R 1 is H;
and wherein at least one of the R 1 and/or R 3 is present in an amount of ≥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 of stearic acid, palmitic acid, 9-ketostearic acid, 10-ketostearic acid and mixtures thereof.

Assignees

• Novamont Spa

Inventors

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

Classifications

• C08G63/16 Primary

  Dicarboxylic acids and dihydroxy compounds · CPC title

• C08K5/11 Primary

  of acyclic polycarboxylic acids · CPC title

• C08K5/10

  Esters; Ether-esters · CPC title

• C08K5/0016

  Plasticisers · CPC title

• C08L27/06

  Homopolymers or copolymers of vinyl chloride · CPC title