IP Library Granted Patent US 12,150,446
Granted Patent B2
US 12,150,446 · App. 17/291,343 · Granted Nov 26, 2024

C3-C6 N-alkyl-gamma-butyrolactam- and peroyxgen-containing antimicrobial compositions

Inventor: Faraz Alderson (Mississauga, CA)
Assignee: DIVERSEY, INC
A01N43/08A01N25/22A01N25/30A01N37/40A01N59/00A01P1/00
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Quick Facts
Patent No.
US 12,150,446
App. No.
17/291,343
Granted
Nov 26, 2024
Kind
B2
Abstract

The use of a C3-C6 N-alkyl-gamma-butyrolactam, e.g. N-butyl-gamma-butyrolactam, to enhance the antimicrobial activity and/or stability of a peroxygen compound (e.g. hydrogen peroxide) in solution, and related compositions and methods. An example antimicrobial composition includes (a) at least one peroxygen compound; (b) at least one C3-C6 N-alkyl-gamma-butyrolactam; and (c) optionally, water, q.s. to 100.

Claims (41)

1. An antimicrobial composition, comprising:

peroxygen compound in an amount of from about 0.5% to about 16% by weight;

C3-C6 N-alkyl-gamma-butyrolactam in an amount of from about 1% to about 25% by weight, based on a total weight of the composition; and

optionally at least one of the following ingredients: water, peroxygen stabilizing agent different from the C3-C6 N-alkyl-gamma-butyrolactam, anionic surfactant, nonionic surfactant, amphoteric surfactant, cationic surfactant, solvent, pH adjusting agent, chelating agent, buffering agent, hydrotrope, skin conditioning agent, anti-foaming agent, additional antimicrobial agent, or any combination thereof.

2. The composition of claim 1 , wherein the peroxygen compound is hydrogen peroxide.

3. The composition of claim 1 , wherein the C3-C6 N-alkyl-gamma-butyrolactam comprises N-butyl-gamma-butyrolactam.

4. The composition of claim 1 , wherein the additional antimicrobial agent comprises carboxylic acid, alcohol, quaternary ammonium compound, phenol, aldehyde, biguanide, mineral acid, halogen compound, glycerol ether, antimicrobial metal, or any combination thereof.

5. The composition of claim 4 , wherein the additional antimicrobial agent comprises carboxylic acid.

6. The composition of claim 5 , wherein the carboxylic acid is present in an amount of from about 0.02% to about 15% by weight based on total weight of the composition.

7. The composition of claim 5 , wherein the carboxylic acid comprises a cyclic carboxylic acid.

8. The composition of claim 5 , wherein the carboxylic acid comprises 2-furoic acid, salicylic acid, mandelic acid, benzoic acid, citric acid, sulfosalicylic acid, sulfosuccinic acid, glycolic acid, lactic acid, formic acid, oxalic acid, malic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, maleic acid, ascorbic acid, alpha-or-beta hydroxy-acetic acid, neopentanoic acid, neoheptanoic acid, neodecanoic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, or any mixture thereof.

9. The composition of claim 1 , wherein the peroxygen stabilizing agent is present in an amount of from about 0.005% to about 20% by weight based on total weight of the composition.

10. The composition of claim 1 , wherein the peroxygen stabilizing agent comprises 1-hydroxyethane-1,1-diphosphonic acid (HEDP), ethylenediaminetetraacetic acid (EDTA), glutamic acid diacetic acid (GLDA), methylglycine diacetic acid (MGDA), polymandelic acid, diethylenetriaminepentaacetic acid (DTPA), N-(hydroxyethyl)-ethylenediaminetriacetic acid (HEDTA), nitrilotriacetic acid (NTA), 2-hydroxyethyliminodiacetic acid (HEIDA), benzoic acid, aminobenzoic acid, citric acid, iminodisuccinic acid, polyaspartic acid, phosphoric acid, tripolyphosphate, amino tri(methylene phosphonic acid) (ATMP), diethylenetriaminepenta(methylene phosphonic acid), 2-hydroxy ethylimino bis(methylene phosphonic acid), ethylene diamine tetra(methylene phosphonic acid), hexamethylenediamine-tetra(methylene phosphonic) acid, or any mixture thereof.

11. The composition of claim 1 , wherein the anionic surfactant is present in an amount of from about 0.02% to about 40% by weight based on total weight of the composition.

12. The composition of claim 1 , wherein the anionic surfactant comprises sulfate, sulfonate, carboxylate, alkyl phosphonate, alkyl ether phosphonate, alkyl phosphate, alkyl ether phosphate, phosphate ester, or any combination thereof.

13. The composition of claim 1 , wherein the anionic surfactant comprises C6-C24 alkylbenzene sulfonate, alkyl sarcosinate, C6-C24 olefin sulfonate, C6-C24 paraffin sulfonate, cumene sulfonate, xylene sulfonate, C6-C24 alcohol sulfates, C6-C24 alcohol ether sulfates having 1 to about 20 ethylene oxide groups, or any mixture thereof.

14. The composition of claim 1 , wherein the composition comprises the solvent that fulfills at least one of the following:

(a) the solvent is present in an amount of from about 0.01% to about 20% by weight based on total weight of the composition;

(b) the solvent comprises cyclic alcohol, carbonate, dimethyl succinate, benzyl acetate, benzyl benzoate, acetophenone, 2-acetyl-1-methylpyrrole, diester dicarboxylate, dialkyl carbonate, organo-nitrile, phthalate ester, propylene glycol derivative with ethoxylation and/or propoxylation, alkoxytriglycol, propylene glycol methyl ether acetate, dipropylene glycol methyl ether acetate, dipropylene glycol n-butyl ether, propylene glycol n-butyl ether, dipropylene glycol n-propyl ether, propylene glycol n-propyl ether, dipropylene glycol methyl ether, tripropylene glycol methyl ether, methanol, ethanol, butyl 3-hydroxybutyrate, isopropyl alcohol, ethylhexylglycerol, diols, non-surfactant emulsifying agent, polar protic solvent, polar aprotic solvent, diethylene glycol monobutyl ether, diethylene glycol monoethyl ether, C1-C8 alcohols, or any mixture thereof.

15. The composition of claim 1 , wherein the composition comprises the pH adjusting agent that fulfills at least one of the following:

(a) the pH adjusting agent is present in an amount of from about 0.01% to about 15% by weight based on total weight of the composition;

(b) the pH adjusting agent comprises phosphoric acid or salt thereof, citric acid or salt thereof, methane sulfonic acid or salt thereof, p-toluene sulfonic acid or salt thereof, potassium hydroxide, sodium hydroxide, or any combination thereof.

16. The composition of claim 1 , wherein the composition comprises nonionic surfactant that fulfills at least one of the following:

(a) the nonionic surfactant is present in an amount of from about 0.02% to about 30% by weight based on total weight of the composition;

(b) the nonionic surfactant comprises alkoxylated surfactant, amine oxides, phosphine oxides, sulfoxide, or any combination thereof.

17. An antimicrobial composition, comprising:

hydrogen peroxide in an amount of from about 0.5% to about 16% by weight;

C3-C6 N-alkyl-gamma-butyrolactam in an amount of from about 1% to about 25% by weight;

water;

optionally carboxylic acid or salt thereof in an amount of from about 0.02% to about 15% by weight;

optionally peroxygen stabilizing agent different from the C3-C6 N-alkyl-gamma-butyrolactam and present in an amount of from about 0.005% to about 20% by weight; and

optionally anionic surfactant in an amount of from about 0.02% to about 40% by weight based on total weight of the composition.

18. The antimicrobial composition of claim 17 , wherein the composition fulfills at least one of the following:

(a) the C3-C6 N-alkyl-gamma-butyrolactam comprises N-butyl-gamma-butyrolactam;

(b) the carboxylic acid comprise 2-furoic acid, salicylic acid, mandelic acid, benzoic acid, citric acid, sulfosalicylic acid, sulfosuccinic acid, glycolic acid, lactic acid, formic acid, oxalic acid, malic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, maleic acid, ascorbic acid, alpha-or-beta hydroxy-acetic acid, neopentanoic acid, neoheptanoic acid, neodecanoic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, or any mixture thereof;

(c) the peroxygen stabilizing agent comprises 1-hydroxyethane-1,1-diphosphonic acid (HEDP), ethylenediaminetetraacetic acid (EDTA), glutamic acid diacetic acid (GLDA), methylglycine diacetic acid (MGDA), polymandelic acid, diethylenetriaminepentaacetic acid (DTPA), N-(hydroxyethyl)-ethylenediaminetriacetic acid (HEDTA), nitrilotriacetic acid (NTA), 2-hydroxyethyliminodiacetic acid (HEIDA), benzoic acid, aminobenzoic acid, citric acid, iminodisuccinic acid, polyaspartic acid, phosphoric acid, tripolyphosphate, amino tri(methylene phosphonic acid) (ATMP), diethylenetriaminepenta(methylene phosphonic acid), 2-hydroxy ethylimino bis(methylene phosphonic acid), ethylene diamine tetra(methylene phosphonic acid), hexamethylenediamine-tetra(methylene phosphonic) acid, or any mixture thereof;

(d) the anionic surfactant comprises C6-C24 alkylbenzene sulfonate, alkyl sarcosinate, C6-C24 olefin sulfonate, C6-C24 paraffin sulfonate, cumene sulfonate, xylene sulfonate, C6-C24 alcohol sulfates, C6-C24 alcohol ether sulfates having 1 to about 20 ethylene oxide groups, or any mixture thereof.

19. A diluted antimicrobial composition, obtained by diluting the antimicrobial composition of claim 17 with water.

20. A method of reducing the number of microbes on a surface, comprising:

applying an antimicrobial composition to the surface at a temperature ranging from about −20° C. to about 80° C. and at an atmospheric pressure of from about 0 PSI to about 50 PSI units, wherein the antimicrobial composition comprises peroxygen compound in an amount of from about 0.5% to about 16% by weight; C3-C6 N-alkyl-gamma-butyrolactam in an amount of from about 1% to about 25% by weight based on total weight of the composition, and optionally at least one of the following ingredients: water, peroxygen stabilizing agent different from the C3-C6 N-alkyl-gamma-butyrolactam, anionic surfactant, nonionic surfactant, amphoteric surfactant, cationic surfactant, solvent, pH adjusting agent, chelating agent, buffering agent, hydrotrope, skin conditioning agent, anti-foaming agent, additional antimicrobial agent, or any combination thereof, and

the microbes comprise bacteria, viruses, fungi, yeasts, mycobacteria, fungal spores, bacterial spores, virinos, viroids, phages, prions, protozoa, parasites, or any combination thereof.

Assignments (10)
RELEASE OF SECURITY INTEREST Recorded Nov 14, 2025
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS NOTES COLLATERAL AGENT
To: BIRKO CORPORATION; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 073564/0864 →
SECURITY INTEREST Recorded Nov 14, 2025
From: CHEM-AQUA, INC.; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; NCH CORPORATION; NCH LIFE SCIENCES LLC; SOLENIS TECHNOLOGIES, L.P.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 073570/0838 →
SECURITY AGREEMENT (NOTES) Recorded Oct 10, 2025
From: DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 073061/0885 →
RELEASE OF 2023 NOTES PATENT SECURITY INTERESTS Recorded Oct 10, 2025
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
To: BIRKO CORPORATION; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 073074/0198 →
SECURITY AGREEMENT (2024 NOTES) Recorded Jun 24, 2024
From: BIRKO CORPORATION; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 067824/0278 →
2023 NOTES PATENT SECURITY AGREEMENT Recorded Jul 7, 2023
From: BIRKO CORPORATION; SOLENIS TECHNOLOGIES, L.P.; INNOVATIVE WATER CARE, LLC; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE GLOBAL CORPORATION
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
Reel/Frame 064225/0170 →
2021 NOTES PATENT SECURITY AGREEMENT Recorded Jul 7, 2023
From: BIRKO CORPORATION; SOLENIS TECHNOLOGIES, L.P.; INNOVATIVE WATER CARE, LLC; DIVERSEY, INC.; DIVERSEY TASKI, INC.
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
Reel/Frame 064225/0576 →
NOTES PATENT SECURITY AGREEMENT Recorded Jul 7, 2023
From: BIRKO CORPORATION; SOLENIS TECHNOLOGIES, L.P.; INNOVATIVE WATER CARE, LLC; DIVERSEY, INC.; DIVERSEY TASKI, INC.
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
Reel/Frame 064348/0235 →
TERM LOAN PATENT SECURITY AGREEMENT Recorded Jul 6, 2023
From: BIRKO CORPORATION; SOLENIS TECHNOLOGIES, L.P.; INNOVATIVE WATER CARE, LLC; DIVERSEY, INC.; DIVERSEY TASKI, INC.
To: GOLDMAN SACHS BANK USA
Reel/Frame 064223/0526 →
ABL PATENT SECURITY AGREEMENT Recorded Jul 6, 2023
From: BIRKO CORPORATION; SOLENIS TECHNOLOGIES, L.P.; INNOVATIVE WATER CARE, LLC; DIVERSEY, INC.; DIVERSEY TASKI, INC.
To: BANK OF AMERICA, N.A.
Reel/Frame 064222/0751 →
Continuity (2)
Provisional Application 62758792 · Nov 12, 2018
Related Publication 20220000108A1 · Jan 6, 2022