Quaternized fatty amines, amidoamines and their derivatives from natural oil

Patent metadata

Field	Value
Publication number	US-9815780-B2
Application number	US-201514867251-A
Country	US
Kind code	B2
Filing date	Sep 28, 2015
Priority date	Oct 25, 2010
Publication date	Nov 14, 2017
Grant date	Nov 14, 2017

Abstract

Quaternary ammonium, betaine, or sulfobetaine compositions derived from fatty amines, wherein the fatty amine is made by reducing the amide reaction product of a metathesis-derived C 10 -C 17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and a secondary amine, are disclosed. Quaternary ammonium, betaine, or sulfobetaine compositions derived from fatty amidoamines, wherein the amidoamine is made by reacting of a metathesis-derived C 10 -C 17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and an aminoalkyl-substituted tertiary amine, are also disclosed. The quaternized compositions are advantageously sulfonated or sulfitated. 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 N made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin. The quaternary ammonium, betaine, and sulfobetaine compositions and their sulfonated or sulfitated derivatives are valuable for a wide variety of end uses, including cleaners, fabric treatment, hair conditioning, personal care (liquid cleansing products, conditioning bars, oral care products), antimicrobial compositions, agricultural uses, and oil field applications.

First claim

We claim:

1. A quaternary ammonium, betaine, or sulfobetaine composition derived from a fatty amidoamine, wherein the amidoamine is made by reacting a metathesis-derived C 10 -C 17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and an aminoalkyl-substituted tertiary amine;
wherein the quaternary ammonium composition has the formula:
R 4 (R 3 )(R 2 )N+(CH 2 ) n NH(CO)R 1 X −

wherein R 1 is —C 9 H 16 —R 5 or —C 16 H 30 —(CO)NH(CH 2 ) n N + (R 2 )(R 3 )R 4 X − ; each of R 2 and R 3 is independently substituted or unsubstituted alkyl, aryl, alkenyl, oxyalkylene, or polyoxyalkylene; R 4 is C 1 -C 6 alkyl; X − is a halide, bicarbonate, bisulfate, or alkyl sulfate; R 5 is hydrogen or C 1 -C 7 alkyl; and n=2 to 8; or
wherein the betaine or sulfobetaine composition has the formula:
R 4 (R 3 )(R 2 )N + (CH 2 ) n NH(CO)R 1

wherein R 1 is —C 9 H 16 —R 5 or —C 16 H 30 —(CO)NH(CH 2 ) n N + (R 2 )(R 3 )R 4 ; each of R 2 and R 3 is independently substituted or unsubstituted alkyl, aryl, alkenyl, oxyalkylene, or polyoxyalkylene; R 4 is C 2 -C 4 alkylene carboxylate, C 2 -C 4 alkylene sulfonate, or C 2 -C 4 hydroxyalkylene sulfonate; R 5 is hydrogen or C 1 -C 7 alkyl; and n=2 to 8;
wherein when R 5 is C 1 -C 7 alkyl, the quaternary ammonium, betaine, or sulfobetaine composition has at least 1 mole % of trans-Δ 9 unsaturation.

2. A derivative made by sulfonating or sulfitating the composition of claim 1 .

3. The composition of claim 1 having at least 25 mole % of trans-Δ 9 unsaturation.

4. The composition of claim 1 having at least 50 mole % of trans-Δ 9 unsaturation.

5. The composition of claim 1 wherein the aminoalkyl-substituted tertiary amine is selected from the group consisting of N,N-dimethylaminopropylamine (DMAPA), N,N-diethylaminopropylamine, N,N-dimethylaminoethylamine, and N,N-dimethylaminobutylamine.

6. The composition of claim 1 wherein 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.

7. The composition of claim 1 wherein the natural oil is selected from the group consisting of soybean oil, palm oil, rapeseed oil, algal oil, and mixtures thereof.

8. The composition of claim 1 wherein the C 10 -C 17 monounsaturated acid or ester derivative comprises a C 10 and a C 12 monounsaturated acid or ester derivative.

9. The composition of claim 1 wherein the C 10 -C 17 monounsaturated acid or ester derivative comprises a C 10 and a C 16 monounsaturated acid or ester derivative.

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

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

12. An antimicrobial composition, a 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 .

13. An antimicrobial composition, a hard-surface cleaner, a laundry detergent formulation, a shampoo or hair conditioner, or a personal cleanser or handsoap, each comprising the derivative of claim 2 .

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

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

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

17. 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
• Ganguly-Mink Sangeeta
• Malec Andrew
• Manuel Teresa
• Masters Ronald A
• Munie Lawrence A
• Murphy Dennis S
• Skelton Patti
• Sook Brian
• Terry Michael R
• Weitgenant Jeremy Aaron
• Whitlock Laura Lee
• Wiester Michael
• Wolfe Patrick Shane

Classifications

• C08G65/2615

  the other compounds containing carboxylic acid, ester or anhydride groups · CPC title

• C07C219/08

  having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton · CPC title

• C07C211/63

  having quaternised nitrogen atoms bound to acyclic carbon atoms · CPC title

• C11D1/74

  Carboxylates or sulfonates {esters} of polyoxyalkylene glycols · CPC title

• C04B24/16

  Sulfur-containing compounds · CPC title