Water stable antimicrobial silanol quaternary ammonium compounds

• US 10,531,664 B2
• Filed: 03/28/2018
• Issued: 01/14/2020
• Est. Priority Date: 04/07/2015
• Status: Active Grant

• Current Assignee: Novalent Limited
• Original Assignee: Indusco, Ltd.
• Inventors: Mason, Joseph E., Neigel, Dennis Victor
• Primary Examiner(s): Kosar, Andrew D
• Assistant Examiner(s): Kenyon, John S
• Application Number:
  US15/938,671
• Publication Number:
  US 20180213792A1
• Time in Patent Office: 657 Days
• CPC Class Codes: A01N 25/04 Dispersions, emulsions, suspoemulsions, suspension concentrates or gels foams A01N25/16
• CPC Class Codes: A01N 25/08 containing solids as carriers or diluents
• CPC Class Codes: A01N 25/10 Macromolecular compounds
• CPC Class Codes: A01N 25/22 containing ingredients stabilising the active ingredients
• CPC Class Codes: A01N 25/34 Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
• CPC Class Codes: A01N 27/00 Biocides, pest repellants or attractants, or plant growth regulators containing hydrocarbons
• CPC Class Codes: A01N 33/12 Quaternary ammonium compounds
• CPC Class Codes: A01N 55/00 Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing organo-phosphorus compounds A01N57/00
• CPC Class Codes: A01N 65/00 Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof containing compounds of determined constitution A01N27/00 - A01N59/00
• CPC Class Codes: A01N 65/06 Coniferophyta [gymnosperms], e.g. cypress
• CPC Class Codes: A01N 65/22 Lamiaceae or Labiatae [Mint family], e.g. thyme, rosemary, skullcap, selfheal, lavender, perilla, pennyroyal, peppermint or spearmint
• CPC Class Codes: A01N 65/28 Myrtaceae [Myrtle family], e.g. teatree or clove
• CPC Class Codes: A01N 65/36 Rutaceae [Rue family], e.g. lime, orange, lemon, corktree or pricklyash
• CPC Class Codes: C09D 5/14 Paints containing biocides, e.g. fungicides, insecticides or pesticides C09D5/16 takes precedence

Abstract

A method of stabilizing aqueous solutions of antimicrobial silanol quaternary ammonium compounds (SQACs) from premature polymerization where the stabilizing agent is selected from a list of antimicrobial, naturally occurring, renewable, volatile, liquid phytochemical essential oils that easily form crystal clear microemulsions when water is added to the concentrated SQAC/essential oil mixture. These non-foaming oil-in-water microemulsions have excellent long term storage stability, remain very low in viscosity and do not phase or precipitate for many months. Many essential oils found to be useful in this process are non-toxic food additives having pleasant scents, have low flammability yet are volatile enough to evaporate upon cure down of the SQAC, resulting in a higher concentration of SQAC in the cured, antimicrobial film. Economically shippable concentrations of stabilized SQACs can be further diluted with water to application concentrations without losing any stabilizing properties and remain storage stable at these lower concentrations indefinitely.

Claims

1. A stabilized aqueous solution of silanol quaternary ammonium compound (SQAC) resistant to premature polymerization comprising:

a mixture formed from an anhydrous SQAC defined as 3-(trimethoxysilyl) propyl-N-octadecyl-N,N-dimethyl ammonium chloride and an essential oil selected from the group consisting of cedarwood oil and pine tree oil, a ratio of a weight of the essential oil to the weight of the SQAC is between about 0.2 and about 0.5; and

a balance of demineralized water to a desired aqueous concentration, whereby the selected essential oil evaporates during a coating or curing of a substrate, allowing a generation of homopolymer crosslinking of a silanol group defined by the SQAC, thereby providing a highly water and solvent insoluble coating on the substrate.

2. The stabilized aqueous solution of claim 1 wherein the anhydrous SQAC is between about 0.1 wt. % and about 10 wt. % of the mixture.

3. The stabilized aqueous solution of claim 1 wherein the anhydrous SQAC is between about 0.1 wt. % and about 1 wt. % of the mixture.

4. The stabilized aqueous solution of claim 1 wherein the anhydrous SQAC is greater than about 0.2 wt. % of the mixture.

5. The stabilized aqueous solution of claim 1 wherein the ratio of a weight of the essential oil to the weight of the anhydrous SQAC is about 0.3.

6. The stabilized aqueous solution of claim 1 further comprising a reaction medium, wherein the reaction medium is a volatile organic reaction medium.

7. The stabilized aqueous solution of claim 6 wherein the volatile organic reaction medium is selected from a group consisting of aliphatic compounds.

8. The stabilized aqueous solution of claim 6 wherein the volatile organic reaction medium is an alcohol.

9. A method of stabilizing the aqueous solution of SQAC in claim 1 from premature polymerization comprising:

mixing an anhydrous SQAC defined as 3-(trimethoxysilyl) propyl-N-octadecyl-N,N-dimethyl ammonium chloride and an essential oil selected from the group consisting of cedarwood oil and pine tree oil to form a mixture,

diluting the mixture to a desired aqueous concentration with demineralized water, and

producing a stable and clear oil-in-water microemulsion that provides long-term stabilization from unwanted polymerization, whereby the selected essential oil evaporates during a coating or curing of a substrate, allowing a generation of homopolymer crosslinking of a silanol group defined by the SQAC, thereby providing a highly water and solvent insoluble coating on the substrate.

10. The method of claim 9 wherein the step of diluting the mixture with demineralized water further comprises diluting the mixture with a volume of water sufficient to produce an oil-in-water microemulsion containing six to ten percent (6-10%) by weight anhydrous SQAC.

11. The method of claim 9 wherein the step of diluting the mixture with demineralized water further comprises diluting the mixture with a volume of water sufficient to produce an oil-in-water microemulsion containing a tenth to six percent (0.1-6.0%) SQAC by weight.

12. The method of claim 9 wherein the step of mixing SQAC with the essential oil further includes defining a weight of the essential oil as five to forty percent (5-40%) by weight when compared to a weight of SQAC included in the mixture.

13. The method of claim 9 wherein the step of mixing SQAC with the essential oil further includes defining a weight of the essential oil as twenty-five to thirty-five percent (25-35%) by weight when compared to a weight (wt/wt) of SQAC present in the mixture.

14. The method of claim 9 wherein the step of producing an oil-in-water microemulsion further comprises producing a stable and clear oil-in-water microemulsion with six percent (6%) SQAC by weight and one and four fifths percent (1.8%) the essential oil by weight, that provides long-term stabilization from unwanted polymerization.

15. The method of claim 14 wherein long-term stabilization is defined as three years at twenty-five degrees Centigrade (25°

C.) without viscosity increase or precipitation.