Dibasic esters and the use thereof in plasticizer compositions

Patent metadata

Field	Value
Publication number	US-10532972-B2
Application number	US-201715499967-A
Country	US
Kind code	B2
Filing date	Apr 28, 2017
Priority date	Mar 17, 2014
Publication date	Jan 14, 2020
Grant date	Jan 14, 2020

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 —, —(CH 2 ) 18 —, —(CH 2 ) 20 —, or —(CH 2 ) 22 —;
R 1 is —(CH 2 —CH 2 —O) 3-12 —(C 1-6 unbranched alkyl); and
R 2 is —(CH 2 —CH 2 —O) 3-12 —(C 1-6 unbranched alkyl).

2. The compound of claim 1 , wherein X 1 is —(CH 2 ) 16 —.

3. The compound of claim 1 , wherein R 1 is —(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 3 .

4. The compound of claim 1 , wherein R 2 is —(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 3 .

5. The compound of claim 1 , wherein R 1 and R 2 are the same.

6. The compound of claim 1 , wherein R 1 and R 2 are not the same.

7. A plasticizer composition, comprising a compound of claim 1 .

8. The plasticizer composition of claim 7 , further comprising one or more additional plasticizers.

9. The plasticizer composition of claim 8 , wherein the one or more additional plasticizers are phthalates, adipates, trimellitic esters, phosphate esters, sebacates, azelates, sulphonates, epoxidized fatty acid esters, or a combination thereof.

10. The plasticizer composition of claim 7 , further comprising one or more additives.

11. The plasticizer composition of claim 10 , wherein the one or more additives are: metal oxides; antioxidants; colorants; color modifiers; diluents; or any combinations thereof.

12. The plasticizer composition of claim 9 , wherein the one or more additional plasticizers are benzenedicarboxylic esters, citraconic esters, 2-hydroxy-1,2,3-propanetricarboxylic esters, malonic esters, succinates, vegetable and animal oils, benzoic esters, triethylene glycol dihexanoate, tetraethylene glycol diheptanoate, linear alkylbenzenes (LABs), branched alkylbenzenes (BABs), polyethylene glycols, polyethylene glycol ethers, polypropylene glycols, polypropylene glycol ethers, or any combinations thereof.

Assignees

• Elevance Renewable Sciences

Inventors

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

Classifications

• C08K5/11

  of acyclic polycarboxylic acids · CPC title

• C07C69/34

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

• C08K5/06 Primary

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

• C07C69/67 Primary

  of saturated acids · CPC title