Fatty amines, amidoamines, and their derivatives from natural oil metathesis

Patent metadata

Field	Value
Publication number	US-9828570-B2
Application number	US-201514867039-A
Country	US
Kind code	B2
Filing date	Sep 28, 2015
Priority date	Oct 25, 2010
Publication date	Nov 28, 2017
Grant date	Nov 28, 2017

Abstract

Fatty amine compositions made from a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives are disclosed. In another aspect, fatty amidoamines made by reacting a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with an aminoalkyl-substituted tertiary amine are disclosed. The fatty amines or amidoamines are advantageously sulfonated, sulfitated, oxidized, or reduced. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin.

First claim

We claim:

1. A fatty amine having the formula:
R 2 (R 3 )NR 1
wherein R 1 is —(CH 2 ) 8 —CH═CHR 4 or —(CH 2 ) 8 —CH═CH—(CH 2 ) 8 —NR 2 R 3 ; each of R 2 and R 3 is independently substituted or unsubstituted alkyl, aryl, alkenyl, oxyalkylene, or polyoxyalkylene; and R 4 is ethyl, wherein the fatty amine has at least 1 mole % of trans-Δ 9 unsaturation.

2. A derivative made by one or more of sulfonating, sulfitating, or oxidizing the fatty amine of claim 1 .

3. The fatty amine of claim 1 wherein the fatty amine has at least 25 mole % of trans-Δ 9 unsaturation.

4. The fatty amine of claim 1 wherein the fatty amine has at least 50 mole % of trans-Δ 9 unsaturation.

5. A glyphosate formulation, a water-soluble herbicide composition, an agricultural solvent, or an anionic emulsifier for agricultural compositions, each comprising the fatty amine of claim 1 .

6. A glyphosate formulation, a water-soluble herbicide composition, an agricultural solvent, or an anionic emulsifier for agricultural compositions, each comprising the derivative of claim 2 .

7. A hard-surface cleaner, a laundry detergent formulation, or a personal cleanser or handsoap, each comprising the fatty amine of claim 1 .

8. A hard-surface cleaner, a laundry detergent formulation, or a personal cleanser or handsoap, each comprising the derivative of claim 2 .

9. A paraffin dispersant, a gas well foamer, or a corrosion inhibitor, each for use in oilfield applications, each comprising the fatty amine of claim 1 .

10. A paraffin dispersant, a gas well foamer, or a corrosion inhibitor, each for use in oilfield applications, each comprising the derivative of claim 2 .

11. A paint or coating additive composition comprising the fatty amine of claim 1 .

12. A paint or coating additive composition comprising the derivative of claim 2 .

13. A foamer, foam additive, or dispersant for use in gypsum, concrete, or firefighting applications comprising the fatty amine of claim 1 .

14. A foamer, foam additive, or dispersant for use in gypsum, concrete, or firefighting applications comprising the derivative of claim 2 .

Assignees

• Stepan Co

Inventors

• Allen Dave R
• Alonso Marcos
• Bernhardt Randal J
• Brown Aaron
• Buchek Kelly
• Luebke Gary
• Luka Renee
• Malec Andrew D
• Masters Ronald A
• Munie Lawrence A
• Murphy Dennis S
• Shapiro Irene
• Skelton Patti
• Sook Brian
• Terry Michael R
• Whitlock Laura Lee
• Wiester Michael
• Wolfe Patrick Shane

Classifications

• C11D1/94

  Mixtures with anionic, cationic or non-ionic compounds · CPC title

• C07C6/04

  at a carbon-to-carbon double bond · CPC title

• C04B38/10

  by using foaming agents (C04B38/02 takes precedence){or by using mechanical means, e.g. adding preformed foam} · CPC title

• A01N25/30

  characterised by the surfactants · CPC title

• C11D1/62

  Quaternary ammonium compounds · CPC title