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

• US 10,323,218 B2
• Filed: 06/04/2018
• Issued: 06/18/2019
• Est. Priority Date: 03/28/2008
• Status: Active Grant

• Current Assignee: Ecolab USA Incorporated (Ecolab, Inc.)
• Original Assignee: Ecolab USA Incorporated (Ecolab, Inc.)
• Inventors: Li, Junzhong, Staub, Richard K., McSherry, David D., Lascotte, Keith G., Lange, Steven J., Everts, Frank
• Primary Examiner(s): Oh, Taylor V
• Application Number:
  US15/997,392
• Publication Number:
  US 20180282669A1
• Time in Patent Office: 379 Days
• Field of Search: 510218, 514557, 514709, 514506, 549556
• CPC Class Codes: A01N 2300/00 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 Class Codes: A01N 25/22 containing ingredients stabilising the active ingredients
• CPC Class Codes: A01N 37/16 containing the group; Thio analogues thereof
• CPC Class Codes: A01N 41/04 Sulfonic acids; Derivatives thereof
• CPC Class Codes: A01N 41/08 Sulfonic acid halides; alpha-Hydroxy-sulfonic acids; Amino-sulfonic acids; Thiosulfonic acids; Derivatives thereof
• CPC Class Codes: A01N 43/20 three- or four-membered rings
• CPC Class Codes: A01N 59/00 Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
• CPC Class Codes: A23B 4/20 Organic compounds; Microorganisms; Enzymes
• CPC Class Codes: A23B 5/14 Organic compounds; Microorganisms; Enzymes
• CPC Class Codes: A23L 3/3535 Organic compounds containing sulfur
• CPC Class Codes: A23V 2002/00 Food compositions, function of food ingredients or processes for food or foodstuffs
• CPC Class Codes: C07C 309/58 Carboxylic acid groups or esters thereof
• CPC Class Codes: C07C 309/60 the carbon skeleton being further substituted by singly-bound oxygen atoms
• CPC Class Codes: C07C 407/00 Preparation of peroxy compounds
• CPC Class Codes: C07C 409/42 containing sulfur atoms
• CPC Class Codes: C07D 303/16 by esterified hydroxyl radicals
• CPC Class Codes: C07D 303/34 with hydrocarbon radicals, substituted by sulphur, selenium or tellurium atoms
• CPC Class Codes: C11D 2111/12 Soft surfaces, e.g. textile
• CPC Class Codes: C11D 3/3472 additionally containing -COOH groups or derivatives thereof
• CPC Class Codes: C11D 3/3942 Inorganic per-compounds C11D3/3902 takes precedence
• CPC Class Codes: C11D 3/3945 : Organic per-compounds C11D3/3902 takes precedence
• CPC Class Codes: C11D 3/395 : Bleaching agents
• CPC Class Codes: C11D 3/48 : Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions

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.

Claims

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

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 C₁ to C₄ carboxylic acid is acetic acid;

and the C₅ to C₁₁ 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:

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:

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:

19. The mixture of claim 13 wherein said sulfoperoxycarboxylic acid

comprises at least one of the following:

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.