Dibasic esters and the use thereof in plasticizer compositions

Patent metadata

Field	Value
Publication number	US-9670132-B2
Application number	US-201514950205-A
Country	US
Kind code	B2
Filing date	Nov 24, 2015
Priority date	Mar 17, 2014
Publication date	Jun 6, 2017
Grant date	Jun 6, 2017

Abstract

Dibasic esters (diesters) and their use in plasticizer compositions are generally disclosed. In some embodiments, the diesters are branched-chain esters of long-chain alkanedioic acids, such as octadecanedioic acid. In some embodiments, such plasticizer compositions are used to increase the plasticity of a polymer resin, such as a vinyl chloride resin or poly vinyl butyral. In some other embodiments, such plasticizer compositions are used to lower the glass transition temperature of a polymer resin. In some embodiments, at least a portion of the plasticizer is derived from a renewable source, such as a natural oil.

First claim

What is claimed is:

1. A compound of formula (I):

wherein:
X 1 is —(CH 2 ) 16 —;
R 1 is 2-methylpentyl, 2-ethylhexyl, 2-butyloctyl, or 3-methylbutyl;
R 2 is a branched or unbranched C 4-24 alkyl, a branched or unbranched C 4-24 alkenyl, a branched or unbranched C 4-30 oxyalkyl, or a branched or unbranched C 4-30 oxyalkenyl, each of which is optionally substituted by one or more substituents selected independently from R 3 ;
R 3 is a halogen atom, —OH, —NH 2 , C 1-6 alkyl, C 1-6 heteroalkyl, C 2-6 alkenyl, or C 2-6 heteroalkenyl.

2. The compound of claim 1 , wherein R 2 is a branched C 4-20 alkyl, a branched C 4-20 alkenyl, a branched C 4-20 oxyalkyl, or a branched C 4-20 oxyalkenyl, each of which is optionally substituted by one or more substituents selected independently from R 3 .

3. The compound of claim 2 , wherein R 2 is a branched C 4-20 alkyl, which comprises branching at the 2-position of the alkyl moiety.

4. The compound of claim 2 , wherein R 2 is a branched C 4-20 alkyl, which comprises branching at the 3-position of the alkyl moiety.

5. The compound of claim 3 , wherein R 2 is a branched C 4-20 alkyl, which has no branching at the 1-position of the alkyl moiety.

6. The compound of claim 2 , wherein R 2 is 2-methylpentyl, 2-ethylhexyl, 2-butyloctyl, or 3-methylbutyl.

7. The compound of claim 1 , wherein R 2 is branched or unbranched C 4-30 oxyalkyl, which is optionally substituted by one or more substituents selected independently from R 3 .

8. The compound of claim 7 , wherein R 2 is —(CH 2 —CH 2 —O) 1-12 —(C 1-6 unbranched alkyl).

9. The compound of claim 8 , wherein R 2 is —CH 2 —CH 2 —O—CH 3 , —(CH 2 —CH 2 —O) 2 —CH 3 , —(CH 2 —CH 2 —O) 3 —CH 3 , —(CH 2 —CH 2 —O) 4 —CH 3 , —(CH 2 —CH 2 —O) 5 —CH 3 , —(CH 2 —CH 2 —O) 6 —CH 3 , —(CH 2 —CH 2 —O) 7 —CH 3 , —(CH 2 —CH 2 —O) 8 —CH 3 , —(CH 2 —CH 2 —O) 9 —CH 3 , —(CH 2 —CH 2 —O) 10 —CH 3 , —(CH 2 —CH 2 —O) 11 —CH 3 , or —(CH 2 —CH 2 —O) 12 —CH 2 —CH 3 .

Assignees

• Elevance Renewable Sciences

Inventors

• Pals Tessa
• Cohen Steven A
• Snead Thomas E
• Beuhler Allyson
• Bertin Paul A

Classifications

• C07C69/67 Primary

  of saturated acids · CPC title

• C08K5/06 Primary

  Ethers; Acetals; Ketals; Ortho-esters · CPC title

• C07C69/34

  Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom · CPC title

• C08K5/11

  of acyclic polycarboxylic acids · CPC title