Antimicrobial mixture containing 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one, and cosmetic composition containing same

Patent metadata

Field	Value
Publication number	US-12521329-B2
Application number	US-201816626089-A
Country	US
Kind code	B2
Filing date	Jun 27, 2018
Priority date	Jun 30, 2017
Publication date	Jan 13, 2026
Grant date	Jan 13, 2026

Abstract

The invention relates to an antimicrobial mixture containing 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and an additional compound chosen from a monovalent or divalent metal salt of pyrithione, piroctone olamine, diazolidinylurea, a hexamidine compound, and imidazolidinylurea,
and also to a cosmetic composition containing such a mixture.
Application to caring for, making up and cleansing keratin materials.

First claim

The invention claimed is:

1 . An antimicrobial mixture comprising 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and an additional compound chosen from:
i) a monovalent or divalent metal salt of pyrithione; ii) piroctone olamine; iii) diazolidinylurea; iv) a hexamidine compound chosen from hexamidine diisethionate, hexamidine diparaben and hexamidine paraben; v) imidazolidinylurea; wherein when the additional compound is a monovalent or divalent metal salt of pyrithione, the antimicrobial mixture comprises 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and the monovalent or divalent metal salt of pyrithione in amounts such that the 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one/pyrithione salt weight ratio ranges from 400 to 4500; when the additional compound is piroctone olamine, the antimicrobial mixture comprises 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and piroctone olamine in amounts such that the 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one/piroctone olamine weight ratio ranges from 10 to 60; when the additional compound is diazolidinylurea, the antimicrobial mixture comprises 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and diazolidinylurea in amounts such that the 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one/diazolidinylurea weight ratio ranges from 0.5 to 2.5; when the additional compound is the hexamidine compound, the antimicrobial mixture comprises 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and the hexamidine compound in amounts such that the 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one/hexamidine compound weight ratio ranges from 5 to 85; when the additional compound is imidazolidinylurea, the antimicrobial mixture comprises 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and imidiazolidinylurea in amounts such that the 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one/imidiazolidinylurea weight ratio ranges from 0.1 to 0.8; and wherein the amounts and ratios of the 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and the additional compound are selected to produce synergistic antimicrobial activity.

2 . The antimicrobial mixture as claimed in claim 1 , wherein the additional compound is a monovalent or divalent metal salt of pyrithione.

3 . The antimicrobial mixture as claimed in claim 2 , wherein the monovalent or divalent metal salt of pyrithione is chosen from the sodium, calcium, magnesium, barium, strontium, zinc, cadmium, tin and zirconium salts.

4 . The antimicrobial mixture as claimed in claim 2 , wherein the monovalent or divalent metal salt of pyrithione is the zinc salt or the sodium salt.

5 . The antimicrobial mixture as claimed in claim 2 , wherein the monovalent or divalent metal salt of pyrithione is the zinc salt.

6 . The antimicrobial mixture as claimed in claim 2 , which has a 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one/pyrithione salt weight ratio ranging from 500 to 2200.

7 . The antimicrobial mixture as claimed in claim 2 , which has a 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one/pyrithione salt weight ratio ranging from 800 to 4500.

8 . The antimicrobial mixture as claimed in claim 1 , wherein the additional compound is piroctone olamine.

9 . The antimicrobial mixture as claimed in claim 8 , which comprises 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one and piroctone olamine in amounts such that the 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one/piroctone olamine weight ratio ranges from 15 to 50.

10 . The antimicrobial mixture as claimed in claim 1 , wherein the additional compound is diazolidinylurea.

11 . The antimicrobial mixture as claimed in claim 10 , which comprises 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one and diazolidinylurea in amounts such that the 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one/diazolidinylurea weight ratio ranges from 0.6 to 2.3.

12 . The antimicrobial mixture as claimed in claim 1 , wherein the additional compound is a hexamidine compound chosen from hexamidine diisethionate, hexamidine diparaben or hexamidine paraben.

13 . The antimicrobial mixture as claimed in claim 12 , wherein the hexamidine compound is hexamidine diisethionate.

14 . The antimicrobial mixture as claimed in claim 12 , which comprises 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one and the hexamidine compound in amounts such that the 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one/hexamidine compound weight ratio ranges from 7 to 82.

15 . The antimicrobial mixture as claimed in claim 1 , wherein the additional compound is imidiazolidinylurea.

16 . The antimicrobial mixture as claimed in claim 15 , which comprises 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one and imidiazolidinylurea in amounts such that the 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one/imidiazolidinylurea weight ratio ranges from 0.15 to 0.45.

17 . The antimicrobial mixture as claimed in claim 15 , which has a 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one/imidiazolidinylurea weight ratio ranging from 0.2 to 0.8, and more preferentially ranging from 0.4 to 0.6.

18 . The antimicrobial mixture as claimed in claim 15 , which has a 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one/imidiazolidinylurea weight ratio ranging from 0.1 to 0.6.

19 . A composition comprising, in a physiologically acceptable medium, an antimicrobial mixture as claimed in claim 1 .

20 . The composition as claimed in claim 19 , which comprises at least one additional ingredient chosen from water, oils, polyols containing from 2 to 10 carbon atoms, gelling agents, surfactants, film-forming polymers, colorants, fragrances, fillers, UV-screening agents, plant extracts, cosmetic and dermatological active agents, and salts.

21 . The composition as claimed in claim 19 , wherein the 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one is present in a content ranging from 0.01% to 5% by weight relative to the total weight of the composition.

22 . A nontherapeutic cosmetic treatment process for caring for and/or making up and/or cleansing keratin materials, comprising the application to said keratin materials of a composition as claimed in claim 19 .

23 . A process for preserving a composition comprising a physiologically acceptable medium, wherein the composition is a cosmetic or dermatological composition, which comprises incorporating into said composition an antimicrobial mixture as defined in claim 1 .

24 . A process for preserving a composition comprising a physiologically acceptable medium which comprises including an antimicrobial mixture as defined in claim 1 in said composition, for preserving a composition comprising a physiologically acceptable medium.

25 . The antimicrobial mixture as claimed in claim 2 , which exhibits synergistic antimicrobial activity against gram positive bacteria.

26 . The antimicrobial mixture as claimed in claim 25 , wherein the gram positive bacteria is Staphylococcus aureus.

27 . The antimicrobial mixture as claimed in claim 2 , which exhibits synergistic antimicrobial activity against Candida albicans.

Assignees

• Oreal

Inventors

• Menard-Szczebara Florence
• Cupferman Sylvie
• Malet Gael
• Galvan Julien

Classifications

• A61Q19/10

  Washing or bathing preparations · CPC title

• A61Q17/04

  Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations · CPC title

• A61Q1/00

  Make-up preparations; Body powders; Preparations for removing make-up · CPC title

• A61K8/4946

  Imidazoles or their condensed derivatives, e.g. benzimidazoles · CPC title

• A61K8/4926

  having six membered rings · CPC title