Imidazoline amides and derivitives from natural oil metathesis

Patent metadata

Field	Value
Publication number	US-9573884-B2
Application number	US-201514847041-A
Country	US
Kind code	B2
Filing date	Sep 8, 2015
Priority date	Oct 25, 2010
Publication date	Feb 21, 2017
Grant date	Feb 21, 2017

Abstract

Fatty amide compositions and their derivatives are disclosed. The fatty amides comprise a reaction product of a metathesis-derived C 10 -C 17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with a primary or secondary amine. Derivatives made by reducing, quaternizing, sulfonating, alkoxylating, sulfating, and sulfitating the fatty amide are also included. The amine reactant can be diethylenetriamine or (2-aminoethyl)ethanolamine, which provide imidazoline amides or esters, respectively. In one aspect, the ester derivative of the C 10 -C 17 monounsaturated acid or octadecene-1,18-dioic acid is a lower alkyl ester. 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. The compositions are valuable for cleaners, fabric treatment, hair conditioning, personal care, antimicrobial compositions, agricultural uses, and oil field applications.

First claim

We claim:

1. A composition comprising:
an imidazoline amide or ester reaction product of diethylenetriamine, (2-aminoethyl)ethanolamine (AEEA), or alkoxylated AEEA with two equivalents of a monounsaturated acid selected from the group consisting of 9-decenoic acid, 9-undecenoic acid, 9-dodecenoic acid, 9-tridecenoic acid, 9-tetradecenoic acid, 9-pentadecenoic acid, 9-hexadecenoic acid, 9-heptadecenoic acid, and octadecene-1,18-dioic acid, or its ester derivative;
wherein the monounsaturated acid or its ester derivative has terminal Δ 9 unsaturation or at least 1 mole % of trans-Δ 9 unsaturation.

2. The composition of claim 1 wherein the monounsaturated acid or its ester derivative has at least 50 mole % of trans-Δ 9 unsaturation.

3. The composition of claim 1 wherein:
the amine is 2-aminoethylethanolamine and the composition comprises an imidazoline ester.

4. An anionic emulsifier for agricultural compositions, a nonionic emulsifier for agricultural compositions, a dispersant for agricultural compositions, a water-soluble herbicide composition, or an agricultural solvent each comprising the composition of claim 1 .

5. An antimicrobial composition comprising the composition of claim 1 .

6. An aqueous hard-surface cleaner, an industrial hard-surface cleaner, a laundry detergent formulation, a shampoo or hair conditioner, or a personal cleanser or handsoap each comprising the composition of claim 1 .

7. A corrosion inhibitor or paraffin dispersant for use in oilfield applications comprising the composition of claim 1 .

8. A paint or coating additive composition comprising the composition of claim 1 .

9. The composition of claim 1 wherein the amine is diethylenetriamine and the composition comprises an imidazoline amide.

10. A derivative made by (a) quaternizing; (b) sulfonating; or (c) quaternizing and sulfonating the composition of claim 1 .

11. An anionic emulsifier for agricultural compositions, a nonionic emulsifier for agricultural compositions, a dispersant for agricultural compositions, a water-soluble herbicide composition, or an agricultural solvent each comprising the derivative of claim 10 .

12. An antimicrobial composition comprising the derivative of claim 10 .

13. An aqueous hard-surface cleaner, an industrial hard-surface cleaner, a laundry detergent formulation, a shampoo or hair conditioner, or a personal cleanser or handsoap each comprising the derivative of claim 10 .

14. A corrosion inhibitor or paraffin dispersant for use in oilfield applications comprising the derivative of claim 10 .

15. A paint or coating additive composition comprising the derivative of claim 10 .

16. An imidazoline amide or ester reaction product of claim 1 having a structure selected from the group consisting of:

17. A derivative of claim 10 having a structure selected from the group consisting of:

Assignees

• Stepan Co

Inventors

• Allen Dave R
• Alonso Marcos
• Bernhardt Randal J
• Brown Aaron
• Buchek Kelly
• Ganguly-Mink Sangeeta
• Holland Brian
• Luebke Gary
• Luka Renee
• Malec Andrew D
• Masters Ronald A
• Murphy Dennis S
• Shapiro Irene
• Skelton Patti
• Sook Brian
• Terry Michael R
• Wallace Gregory
• Whitlock Laura Lee
• Wiester Michael
• Wolfe Patrick Shane
• Titievsky Lena

Classifications

• C07C303/18

  by reaction of sulfides with compounds having functional groups with formation of sulfo or halosulfonyl groups · CPC title

• C08K5/42

  Sulfonic acids; Derivatives thereof · CPC title

• C07D233/24

  Radicals substituted by nitrogen atoms not forming part of a nitro radical · CPC title

• C07C231/12

  by reactions not involving the formation of carboxamide groups · CPC title

• A61Q5/02

  Preparations for cleaning the hair · CPC title