Unsaturated fatty alcohol alkoxylates from natural oil metathesis

Patent metadata

Field	Value
Publication number	US-9708251-B2
Application number	US-201314395829-A
Country	US
Kind code	B2
Filing date	Mar 13, 2013
Priority date	Apr 24, 2012
Publication date	Jul 18, 2017
Grant date	Jul 18, 2017

Abstract

Unsaturated fatty alcohol alkoxylates, processes for making them, and methods of using them are disclosed. In one aspect, a monounsaturated fatty alcohol alkoxylate is made by reducing a metathesis-derived monounsaturated alkyl ester, followed by alkoxylation of the resulting monounsaturated alcohol. Microscopy reveals that the monounsaturated alkoxylates have isotropic and lamellar phases over a wider range of actives levels compared with their saturated analogs. This attribute expands formulating latitude for many end-use applications. The unsaturated fatty alcohol alkoxylates are valuable in, for example, agricultural solvents, nonionic emulsifiers for agricultural compositions, hard surface cleaners, laundry detergents, specialty foams, additives or surfactants for paints or coatings, and surfactant compositions for enhanced oil recovery.

First claim

We claim:

1. A fatty alcohol alkoxylate having the general structure:
R—CH═CH—(CH 2 ) 7 —CH 2 O-(AO) n —H

wherein R is H or C 2 alkyl; AO is an oxyalkylene group; and n, which is the average number of oxyalkylene groups, has a value within the range of 1 to 50 wherein when R is C 2 alkyl, the alkoxylate has at least 1 mole % of trans-Δ 9 unsaturation.

2. A liquid surfactant composition comprising the alkoxylate of claim 1 , wherein the surfactant can be processed, formulated, or both at a higher actives level compared with that of a similar composition comprising a saturated analog of the alkoxylate.

3. A mixture comprising water and from 1 to 80 wt %, based on the amount of mixture, of the alkoxylate of claim 1 .

4. A fatty alcohol ethoxylate of claim 1 .

5. The fatty alcohol ethoxylate of claim 4 wherein n has a value within the range of 1 to 20.

6. A mixture comprising water and from 1 to 80 wt. %, based on the amount of mixture, of the ethoxylate of claim 4 .

7. A monounsaturated fatty alcohol ethoxylate of claim 4 having at least one isotropic clear phase over an increased actives level range when compared with that of a saturated analog of the monounsaturated fatty alcohol ethoxylate.

8. The fatty alcohol ethoxylate of claim 7 comprising isotropic and/or lamellar phases at any actives level from 0 to 100%.

9. The fatty alcohol ethoxylate of claim 7 comprising an isotropic clear phase at any actives level from 0 to 100%.

10. A mixture comprising water and from 1 to 80 wt. %, based on the amount of mixture, of the ethoxylate of claim 7 .

11. A nonionic emulsifier for agricultural compositions comprising the alkoxylate of claim 1 .

12. A nonionic emulsifier for agricultural compositions comprising the ethoxylate of claim 4 .

13. An agricultural solvent comprising the alkoxylate of claim 1 .

14. An agricultural solvent comprising the ethoxylate of claim 4 .

15. An aqueous hard surface cleaner comprising the alkoxylate of claim 1 .

16. An aqueous hard surface cleaner comprising the ethoxylate of claim 4 .

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

18. A paint or coating additive composition comprising the ethoxylate of claim 4 .

19. A laundry detergent formulation comprising the alkoxylate of claim 1 .

20. A laundry detergent formulation comprising the ethoxylate of claim 4 .

21. A foamer, foam additive, or dispersant for use in gypsum, concrete, or fire-fighting applications comprising the alkoxylate of claim 1 .

22. A foamer, foam additive, or dispersant for use in gypsum, concrete, or fire-fighting applications comprising the ethoxylate of claim 4 .

23. A surfactant composition for use in enhanced oil recovery, comprising the alkoxylate of claim 1 .

24. A surfactant composition for use in enhanced oil recovery, comprising the ethoxylate of claim 4 .

Assignees

• Stepan Co

Inventors

• Allen David R
• Alonso Marcos
• Beddaoui Mary
• Bernhardt Randal J
• Brown Aaron
• Dong Xue Min
• Gorman Wilma
• Hutchison John
• Luebke Gary
• Luka Renee
• Luxem Franz
• Malec Andrew D
• Masters Ronald A
• Murphy Dennis S
• Skelton Patti
• Sook Brian
• Spaulding Chris
• Wiester Michael
• Wolfe Patrick Shane

Classifications

• C11D1/143

  Sulfonic acid esters · CPC title

• A61K8/463

  containing sulfuric acid derivatives, e.g. sodium lauryl sulfate · CPC title

• C07C309/08

  containing hydroxy groups bound to the carbon skeleton · CPC title

• C11D1/146

  Sulfuric acid esters · CPC title

• C07C303/32

  of salts of sulfonic acids · CPC title