Surfactants based on monounsaturated fatty alcohol derivatives

Patent metadata

Field	Value
Publication number	US-9695385-B2
Application number	US-201414770912-A
Country	US
Kind code	B2
Filing date	Mar 5, 2014
Priority date	Mar 13, 2013
Publication date	Jul 4, 2017
Grant date	Jul 4, 2017

Abstract

Surfactant compositions comprising an alkoxylate, a sulfate, or ether sulfate of a C 10 -C 12 monounsaturated alcohol are disclosed. The alkoxylate, sulfate, or ether sulfate may derive from undecylenic acid or undecylenic alcohol. Compared with their saturated analogs, the monounsaturated alkoxylates, sulfates, and ether sulfates are less irritating, making them valuable for personal care, laundry, cleaners, and other household applications. Microscopy studies show that the alkoxylates, sulfates, and ether sulfates have favorable phase behavior over a wide range of actives levels, expanding opportunities for products with greater compaction. When combined with cationic surfactants, the alkoxylates, sulfates, and ether sulfates exhibit synergy, and they have improved solubility compared with their saturated analogs. The surfactants find value for the personal care, laundry and cleaning, emulsion polymerization, agricultural products, oilfield applications, and specialty foams industries.

First claim

We claim:

1. A process which comprises reacting a composition comprising a monounsaturated C 10 -C 12 alcohol with an alkoxylating agent, a sulfating agent, or an alkoxylating agent followed by a sulfating agent to make, respectively, an alkoxylate, a sulfate, or an ether sulfate.

2. The process of claim 1 wherein the monounsaturated C 10 -C 12 alcohol or alkoxylate is reacted with sulfur trioxide in a falling-film reactor, followed by neutralization.

3. A process for making an internally monounsaturated C 10 -C 12 alcohol sulfate or ether sulfate, the process comprising reacting a terminally monounsaturated C 10 -C 12 alcohol or alkoxylate with sulfur trioxide in a falling-film reactor, followed by neutralization.

4. A composition comprising water and 1 to 99 wt. % of a surfactant, wherein the surfactant comprises an ether sulfate of the formula:
CH 2═ CH—(CH 2 ) 9 —O—(EO) n —SO 4 − M =

wherein n is the average number of EO units and has a value from 1 to 5, and M is Na, K, Li, or NH 4 .

5. The composition of claim 4 wherein M is Na or NH 4 .

6. The composition of claim 4 wherein M is Na and n is 1 or 3.

7. The composition of claim 4 wherein M is NH 4 and n is 1.

8. A composition comprising water and 1 to 99 wt. % of a surfactant comprising sulfates of undecylenic alcohol, wherein the surfactant comprises:
(a) 40 to 60 wt. % of a monounsaturated C 11 primary alcohol sulfate; and
(b) 40 to 60 wt. % of a secondary hydroxyalkyl C 11 primary alcohol sulfate.

9. The composition of claim 8 comprising 2 to 98 wt. % of the surfactant.

10. The composition of claim 8 wherein the surfactant further comprises 0.1 to 20 wt. % of sulfonated products.

11. The composition of claim 8 made by sulfating undecylenic alcohol with sulfur trioxide in a falling-film reactor, followed by neutralization.

Assignees

• Stepan Co

Inventors

• Allen David R
• Bernhardt Randal J
• Brown Aaron
• Dado Gregory P
• Dong Xue Min
• Gorman Wilma
• Masters Ronald
• Skelton Patti

Classifications

• C11D1/146 Primary

  Sulfuric acid esters · CPC title

• C07C305/10

  being further substituted by singly-bound oxygen atoms · CPC title

• A01N25/00

  Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application {, e.g. seed treatment or sequential application}; Substances for reducing the noxious effect of the active ingredients to organisms other than pests · CPC title

• A01N25/30 Primary

  characterised by the surfactants · CPC title