Conjugated Diene Acids and Derivatives Thereof

Patent metadata

Field	Value
Publication number	US-2016016882-A1
Application number	US-201514799218-A
Country	US
Kind code	A1
Filing date	Jul 14, 2015
Priority date	Jul 21, 2014
Publication date	Jan 21, 2016
Grant date	—

Abstract

Conjugated diene acids and derivatives thereof, are disclosed herein. In some embodiments, the conjugated diene acids and derivatives thereof are derived from the metathesis of a natural oil followed by isomerization. Uses of conjugated diene acids and derivatives thereof in various compositions are also disclosed herein.

First claim

1 . A compound of formula (I):

wherein
R 1 is a hydrogen atom, C 1-20 alkyl, C 2-20 alkenyl, C 1-20 heteroalkyl, C 2-20 heteroalkenyl, C 6-20 aryl, or C 4-20 heteroaryl, wherein the alkyl, alkenyl, heteroalkyl, heteroalkenyl, aryl, and heteroaryl groups are optionally substituted one or more times by substituents selected independently from R 4 ;
R 2 and R 3 are independently a hydrogen atom, C 1-20 alkyl, C 2-20 alkenyl, C 1-20 heteroalkyl, C 2-20 heteroalkenyl, C 6-20 aryl, or C 4-20 heteroaryl, wherein the alkyl, alkenyl, heteroalkyl, heteroalkenyl, aryl, and heteroaryl groups are optionally substituted one or more times by substituents selected independently from R 4 ;
G 1 is a straight-chain C 7 alkylene group, which is optionally substituted one or more times by substituents selected independent from R 4 ;
G 2 is a direct bond or is a C 1 alkylene group, which is optionally substituted one or two times by substituents selected independent from R 4 ; and
R 4 is a halogen atom, —OH, —NH 2 , C 1-6 alkyl, C 6-20 aryl, or C 4-20 heteroaryl, C 1-6 heteroalkyl, C 2-6 alkenyl, or C 2-6 heteroalkenyl.

2 . The compound of claim 1 , wherein R 1 is a hydrogen atom, C 1-12 alkyl, or C 1-12 oxyalkyl, wherein the alkyl or oxyalkyl groups are optionally substituted one or more times by substituents selected independently from the group consisting of —OH and —O(C 1-6 alkyl).

3 . The compound of claim 2 , wherein R′ is a hydrogen atom or C 1-12 alkyl.

4 . The compound of claim 3 , wherein R 1 is a hydrogen atom.

5 . The compound of claim 3 , wherein R 1 is methyl, ethyl, or isopropyl.

6 . The compound of claim 1 , wherein at least one of R 2 and R 3 is a hydrogen atom, and the other is a hydrogen atom or C 1-12 alkyl.

7 . The compound of claim 6 , wherein both R 2 and R 3 are both a hydrogen atom.

8 . The compound of claim 6 , wherein one of R 2 and R 3 is a hydrogen atom and the other is methyl, ethyl, or propyl.

9 . The compound of claim 8 , wherein one of R 2 and R 3 is a hydrogen atom and the other is methyl.

10 . The compound of claim 8 , wherein one of R 2 and R 3 is a hydrogen atom and the other is ethyl.

11 . The compound of claim 8 , wherein one of R 2 and R 3 is a hydrogen atom and the other is propyl.

12 . The compound of claim 1 , wherein G 1 is —(CH 2 ) 7 —.

13 . The compound of claim 1 , wherein G 2 is a direct bond or is —CH 2 —.

14 . The compound of claim 13 , wherein G 2 is a direct bond.

15 . The compound of claim 13 , wherein G 2 is —CH 2 —.

16 . A composition comprising: a compound of claim 1 .

17 . The composition of claim 16 , further comprising water.

18 . The composition of claim 17 , wherein the composition is an oil-in-water emulsion.

19 - 23 . (canceled)

24 . A synthetic rubber composition, which is formed from a reaction mixture comprising: styrene, butadiene, and a compound of claim 1 .

25 . A rubber article comprising the synthetic rubber composition of claim 24 .

Assignees

• Elevance Renewable Sciences

Inventors

• Littich Ryan
• Coburn Charles

Classifications

• A23K20/158

  Fatty acids; Fats; Products containing oils or fats · CPC title

• A01N25/04

  Dispersions, {emulsions, suspoemulsions, suspension concentrates} or gels (foams A01N25/16) · CPC title

• C11C3/14

  by isomerisation {(isomerisation induced by hydrogenation C11C3/12)} · CPC title

• C07C69/587 Primary

  Monocarboxylic acid esters having at least two carbon-to-carbon double bonds · CPC title

• C11C3/003

  by esterification of fatty acids with alcohols (C11C3/02 takes precedence) · CPC title