Fatty amides and derivatives from natural oil metathesis

Patent metadata

Field	Value
Publication number	US-10322994-B2
Application number	US-201715403288-A
Country	US
Kind code	B2
Filing date	Jan 11, 2017
Priority date	Oct 25, 2010
Publication date	Jun 18, 2019
Grant date	Jun 18, 2019

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 a fatty amide, wherein the fatty amide has a structure selected from the group consisting of:

wherein fatty amides (b) and (c) have at least 1 mole % of trans-Δ 9 unsaturation.

2. An amide sulfonate made by sulfonating the composition of claim 1 .

3. The composition of claim 1 wherein the fatty amide has the structure:

4. A composition comprising a fatty amide, wherein the fatty amide has a structure selected from the group consisting of:

wherein fatty amides (b), (c), (e), and (f) have at least 1 mole % of trans-Δ 9 unsaturation.

5. An amide sulfonate made by sulfonating the composition of claim 4 .

6. An anionic emulsifier for agricultural compositions, a nonionic emulsifier for agricultural compositions, a dispersant for agricultural compositions, a water-soluble herbicide composition, an agricultural solvent, an antimicrobial composition, an aqueous hard-surface cleaner, an industrial hard-surface cleaner, a laundry detergent formulation, a shampoo or hair conditioner, a personal cleanser or handsoap, a corrosion inhibitor for use in oilfield applications, a paraffin dispersant for use in oilfield applications, or a paint or coating additive composition comprising the composition of claim 1 .

7. An anionic emulsifier for agricultural compositions, a nonionic emulsifier for agricultural compositions, a dispersant for agricultural compositions, a water-soluble herbicide composition, an agricultural solvent, an antimicrobial composition, an aqueous hard-surface cleaner, an industrial hard-surface cleaner, a laundry detergent formulation, a shampoo or hair conditioner, a personal cleanser or handsoap, a corrosion inhibitor for use in oilfield applications, a paraffin dispersant for use in oilfield applications, or a paint or coating additive composition comprising the amide sulfonate of claim 2 .

8. An anionic emulsifier for agricultural compositions, a nonionic emulsifier for agricultural compositions, a dispersant for agricultural compositions, a water-soluble herbicide composition, an agricultural solvent, an antimicrobial composition, an aqueous hard-surface cleaner, an industrial hard-surface cleaner, a laundry detergent formulation, a shampoo or hair conditioner, a personal cleanser or handsoap, a corrosion inhibitor for use in oilfield applications, a paraffin dispersant for use in oilfield applications, or a paint or coating additive composition comprising the composition of claim 4 .

9. An anionic emulsifier for agricultural compositions, a nonionic emulsifier for agricultural compositions, a dispersant for agricultural compositions, a water-soluble herbicide composition, an agricultural solvent, an antimicrobial composition, an aqueous hard-surface cleaner, an industrial hard-surface cleaner, a laundry detergent formulation, a shampoo or hair conditioner, a personal cleanser or handsoap, a corrosion inhibitor for use in oilfield applications, a paraffin dispersant for use in oilfield applications, or a paint or coating additive composition comprising the amide sulfonate of claim 5 .

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

• C08K5/42

  Sulfonic acids; Derivatives thereof · CPC title

• A01N25/04

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

• C11D1/002

  Surface-active compounds containing sulfur (SO3 and SO4, C11D1/12; sulfonium compounds C11D1/60; sulfoxides C11D1/755; sulfobetaines C11D1/92) · CPC title

• A61Q5/12

  Preparations containing hair conditioners · CPC title

• C08K5/20

  Carboxylic acid amides · CPC title