Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents

Patent metadata

Field	Value
Publication number	US-10323218-B2
Application number	US-201815997392-A
Country	US
Kind code	B2
Filing date	Jun 4, 2018
Priority date	Mar 28, 2008
Publication date	Jun 18, 2019
Grant date	Jun 18, 2019

Abstract

The present invention relates to novel sulfoperoxycarboxylic acid compounds, and methods for making and using them. The sulfoperoxycarboxylic compounds of the invention are storage stable, water soluble and have low to no odor. Further, the compounds of the present invention can be formed from non-petroleum based renewable materials. The compounds of the present invention can be used as antimicrobials, and bleaching agents. The compounds of the present invention are also suitable for use as coupling agents.

First claim

What is claimed is:

1. A sulfoperoxycarboxlic acid having one of the following formulas:

or a salt, thereof.

2. A composition comprising a mixture of 2 or more of the sulfoperoxycarboxlic acids of claim 1 .

3. The use composition of claim 1 wherein the C 1 to C 4 carboxylic acid is acetic acid; and the C 5 to C 11 carboxylic acid is octanoic acid.

4. The cleaning composition of claim 3 further comprising a surfactant.

5. The cleaning composition of claim 4 wherein said surfactant is an anionic surfactant.

6. The cleaning composition of claim 1 wherein said sulfoperoxycarboxylic acid comprises at least one of the following:

or salts thereof.

7. The use composition of claim 2 , wherein the oxidizing agent comprises hydrogen peroxide.

8. The mixture of claim 2 wherein said sulfoperoxycarboxylic acid comprises at least one of the following:

or salts thereof.

9. The mixture of claim 8 comprising 2 or more sulfoperoxycarboxylic acids.

10. The mixture of claim 8 comprising 3 or more sulfoperoxycarboxylic acids.

11. The mixture of claim 8 comprising 4 sulfoperoxycarboxylic acids.

12. A cleaning composition comprising one of more of the sulfoperoxycarboxlic acids of claim 1 .

13. A mixture of sulfoperoxycarboxylic acids made by
Obtaining a sulfonated fatty acid, and thereafter
mixing said sulfonated fatty acid with hydrogen peroxide to form an acid catalyzed equilibrium thereby converting said sulfonated fatty acid to a sulfoperoxycarboxylic acid.

14. The mixture of claim 13 wherein said sulfonated fatty acid is 11-sulfoundecanoic acid, 10,11-disulfoundecanoic acid, sulfonated oleic acid, sulfonated linoleic acid, sulfonated palmitoleic acid or sulfonated stearic acid.

15. The mixture of claim 13 wherein said sulfoperoxycarboxlic acid is formed by direct acid catalyzed equilibrium action of hydrogen peroxide.

16. The mixture of claim 13 wherein said resultant sulfonated percarboxylic acids are not sulfonated at the α position.

17. The mixture of claim 13 wherein the carbon on the carbon backbone of the percarboxylic acid chain that is directly connected to, the carboxylic acid group is not sulfonated.

18. The mixture of claim 13 wherein said mixture is two or more of the following:

or a salt, thereof.

19. The mixture of claim 13 wherein said sulfoperoxycarboxylic acid
comprises at least one of the following:

or salts thereof.

20. A method of making a sulfoperoxycarboxlic acid comprising:
(a) Obtaining a sulfonated fatty acid, and
(b) Introducing said sulfonated fatty acid to hydrogen peroxide so that a peroxycarboxylic acid is formed in an acid catalyzed equilibrium.

21. The method of claim 20 wherein said sulfonated fatty acid is 11-sulfoundecanoic acid, 10,11-disulfoundecanoic acid, sulfonated oleic acid, sulfonated linoleic acid, sulfonated palmitoleic acid or sulfonated stearic acid.

22. The method of claim 20 wherein the method of making is not impacted by pH.

23. The method of claim 20 wherein said resultant sulfonated percarboxylic acids are not sulfonated at the α position.

24. The method of claim 20 wherein the carbon on the carbon backbone of the percarboxylic acid chain that is directly connected to, the carboxylic acid group is not sulfonated.

25. The method of claim 20 wherein said fatty acid is sulfonated after it is converted to a percarboxylic acid.

Assignees

• Ecolab Usa Inc

Inventors

• Li Junzhong
• Staub Richard K
• Mcsherry David D
• Lascotte Keith G
• Lange Steven J
• Everts Frank

Classifications

• C07C407/00

  Preparation of peroxy compounds · CPC title

• A01N2300/00

  Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48 · CPC title

• A01N43/20

  three- or four-membered rings · CPC title

• C11D3/3945 Primary

  Organic per-compounds (C11D3/3902 takes precedence) · CPC title

• C11D3/3472

  additionally containing -COOH groups or derivatives thereof · CPC title