Compositions containing tetrahydrofurfuryl and/or alkyl-substituted tetrahydrofurfuryl esters of citric acid

Patent metadata

Field	Value
Publication number	US-9670335-B2
Application number	US-201314387596-A
Country	US
Kind code	B2
Filing date	Mar 14, 2013
Priority date	Mar 30, 2012
Publication date	Jun 6, 2017
Grant date	Jun 6, 2017

Abstract

Compositions containing tetrahydrofurfuryl and/or alkyl-substituted tetrahydrofurfuryl esters of citric acid are provided. These esters of citric acid can be formed from renewable materials and can be used, for example, as plasticizers for various polymeric materials. The tetrahydrofurfuryl and/or alkyl-substituted tetrahydrofurfuryl esters of citric acid typically have a low odor, have good compatibility with a variety of polymeric materials, and can be used at temperatures often encountered during hot melt processing of polymeric materials.

First claim

What is claimed is:

1. A composition comprising:
a) at least two different citrate esters of Formula (I)

wherein
each R 1 is an alkyl, tetrahydrofurfuryl group, or alkyl-substituted tetrahydrofurfuryl group, wherein at least one R 1 is a tetrahydrofurfuryl group or alkyl-substituted tetrahydrofurfuryl group; and
R 2 is hydrogen or an acyl group.

2. The composition of claim 1 , wherein the composition further comprises a polymeric material.

3. The composition of claim 2 , wherein the polymeric material is a thermoplastic polymer that is an aliphatic polyester, a cellulose ester, polyvinyl chloride, or an acrylic polymer.

4. The composition of claim 2 , wherein the polymeric material is an elastomeric polymer.

5. The composition of claim 2 , wherein the composition comprises 5 to 50 weight percent citrate esters of Formula (I) and 50 to 95 weight percent polymeric material based on a total weight of the composition.

6. An article comprising the composition of claim 2 .

7. A composition comprising:
a) at least one citrate ester of Formula (I)

wherein
each R 1 is an alkyl, tetrahydrofurfuryl group, or alkyl-substituted tetrahydrofurfuryl group, wherein at least one R 1 is a tetrahydrofurfuryl group or alkyl-substituted tetrahydrofurfuryl group; and
R 2 is hydrogen or an acyl group; and

b) at least one citrate ester of Formula (II)

wherein
each R 3 is an alkyl; and
R 4 is hydrogen or an acyl group.

8. The composition of claim 7 , wherein the composition further comprises a polymeric material.

9. The composition of claim 8 , wherein the polymeric material is a thermoplastic polymer comprising an aliphatic polyester, a cellulose ester, polyvinyl chloride, or an acrylic polymer.

10. The composition of claim 8 , wherein the polymeric material is an elastomeric polymer.

11. The composition of claim 8 , wherein the composition comprises 5 to 50 weight percent of the sum of citrate esters of Formula (I) plus the citrate ester of Formula (II) and 50 to 95 weight percent polymeric material based on a total weight of the composition.

12. An article comprising the composition of claim 8 .

13. The composition of claim 1 , wherein one of the citrate esters of Formula (I) is the following Formula (III):

wherein
each R 5 is tetrahydrofurfuryl group or alkyl-substituted tetrahydrofurfuryl group; and
R 6 is hydrogen or an acyl.

14. The composition of claim 7 , wherein the compound of Formula (I) is the following Formula (III):

wherein
each R 5 is tetrahydrofurfuryl group or alkyl-substituted tetrahydrofurfuryl group; and
R 6 is hydrogen or an acyl.

15. The composition of claim 14 , wherein the composition further comprises a polymeric material.

16. An article comprising the composition of claim 15 .

Assignees

• 3M Innovative Properties Co

Inventors

• Kavanagh Maureen A
• Lewandowski Kevin M

Classifications

• C08K5/11

  of acyclic polycarboxylic acids · CPC title

• C08K5/1535 Primary

  Five-membered rings · CPC title

• C07D307/12

  Radicals substituted by oxygen atoms · CPC title

• C07D405/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D405/14

  containing three or more hetero rings · CPC title