Antimicrobial mixture containing 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and an acid or silver-based compound, and cosmetic composition containing same

Patent metadata

Field	Value
Publication number	US-12256733-B2
Application number	US-201917286872-A
Country	US
Kind code	B2
Filing date	Dec 6, 2019
Priority date	Dec 21, 2018
Publication date	Mar 25, 2025
Grant date	Mar 25, 2025

Abstract

The invention relates to an antimicrobial mixture containing 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and an acid and/or silver-based compound, and also to a cosmetic, pharmaceutical or nutritional composition containing such a mixture.
Application to caring for, making up and cleansing keratin materials; to preserving foods and to water treatment.

First claim

The invention claimed is:

1. A synergistic antimicrobial mixture comprising:
4-(3-ethoxy-4-hydroxyphenyl) butan-2-one and salts thereof with an organic or inorganic acid or base, and solvates thereof; and
at least one acid compound chosen from:

i) ethylenediaminedisuccinic acid and salts thereof;
ii) jasmonate compounds (I) and salts thereof;

in which formula (I) R denotes a saturated or unsaturated linear hydrocarbon-based radical containing from 2 to 7 carbon atoms;
iii) glycinate compounds of formula (II) and the salts thereof:
R 1 R 2 NCH 2 COO − X +   (II)

R 1 and R 2 denoting a hydrogen atom or a hydroxy (C 1 -C 4 ) alkyl group;
X + denoting a cationic counterion;
or at least one silver-based compound chosen from:

i) silver I and II oxides,
ii) silver particles;
iii) Ag I or Ag II salts chosen from the following formulae:
a) AgHal with Hal representing a halogen atom;
b) AgHal 2 , with Hal being identical or different; and
c) Ag x R 3 2 and also solvates thereof, with
R 3 , which may be identical or different, representing a group chosen from:
sulfate;
nitrate;
hydroxy;
(C 1 -C 6 ) alkylcarboxylate in which the (C 1 -C 6 ) alkyl group is linear or branched and is optionally substituted with one or more hydroxyl, carboxyl or carboxylate groups;
an aryl group substituted with at least one carboxylate group and optionally substituted with one or more hydroxyl groups; and

x and z are integers such that 1≤z≤6, 1≤x≤4;

wherein the 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one and salts thereof with an organic or inorganic acid or base, and solvates thereof and the at least one acid compound or at least one silver-based compound are in synergistically effective amounts such that the mixture results in synergistic antimicrobial activity due to the 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one and salts thereof with an organic or inorganic acid or base, and solvates thereof and the at least one acid compound or at least one silver-based compound; and wherein
when the mixture comprises ethylenediaminedisuccinic acid or salts thereof, the 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one and ethylenediaminedisuccinic acid or salts thereof are present in said mixture in a weight ratio such that the 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one/ethylenediaminedisuccinic acid or salts thereof weight ratio ranges from 1.5 to 15;
when the mixture comprises the jasmonate compounds (I), the 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one and the jasmonate compounds (I) are present in said mixture in a content such that the weight ratio ranges from 0.3 to 1.20;
when the mixture comprises the glycinate compounds of formula (II, the 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one and the glycinate compounds of formula (II) and the salts thereof are present in said mixture in a content such that the 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one/glycinate compounds of formula (II) or salts thereof weight ratio ranges from 10 to 80; and
when the mixture comprises a silver-based compound; the 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one and the silver-based compounds are present in said mixture in a content such that the 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one/silver-based compound weight ratio ranges from 0.4 to 4.

2. The mixture as claimed in claim 1 , wherein the salts are chosen from the salts of alkali metals or alkaline-earth metals, aluminum or zinc, or ammonium salts of (C 1 -C 4 ) alkanolamine.

3. The mixture as claimed in claim 1 , wherein the 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one and ethylenediaminedisuccinic acid or salts thereof are present in said mixture in a weight ratio such that the 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one/ethylenediaminedisuccinic acid or salts thereof weight ratio ranges from 2.5 to 15 and which exhibits synergism against Gram-positive bacterium.

4. The mixture as claimed in claim 1 , wherein the compound of formula (I) is chosen from 3-hydroxy-2-[2-pentenyl]cyclopentaneacetic acid or 3-hydroxy-2-pentylcyclopentaneacetic acid and/or salts thereof.

5. The mixture as claimed in claim 1 , wherein the 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one and the jasmonate compounds (I) are present in said mixture in a content such that the weight ratio ranges from 0.45 to 1.20 and which exhibits synergism against yeast.

6. The mixture as claimed in claim 1 , wherein the glycinate compound (II) and the salts thereof are chosen from hydroxymethylglycinate salts.

7. The mixture as claimed in claim 1 , wherein—the 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one and the glycinate compounds of formula (II) and the salts thereof are present in said mixture in a content such that the 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one/glycinate compounds of formula (II) or salts thereof weight ratio ranges from 20 to 60 and which exhibits synergism against Gram-positive bacterium.

8. The mixture as claimed in claim 1 , wherein the silver-based (Ag) compounds are chosen from silver (C 1 -C 6 ) alkylcarboxylates.

9. The mixture as claimed in claim 1 , wherein 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one and the silver-based compounds are present in said mixture in a content such that the 4-(3-ethoxy-4-hydroxyphenyl) butan-2-one/silver-based compound weight ratio ranges from 0.4 to 3.6 and which exhibits synergism against mold.

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

11. The composition as claimed in claim 10 , 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, dyestuffs, fragrances, fillers, UV-screening agents, plant extracts, cosmetic and dermatological active agents, and salts.

12. The composition as claimed in claim 10 , 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.

13. 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 10 .

14. A process for conserving a composition, comprising a physiologically acceptable medium, which comprises incorporating into said composition an antimicrobial mixture as claimed in claim 1 .

15. A process for preserving a cosmetic or pharmaceutical composition which comprises incorporating into said composition an antimicrobial mixture as defined in claim 1 .

16. A nutritional composition comprising an antimicrobial mixture as claimed in claim 10 .

17. A process for preserving a nutritional composition, which comprises incorporating into said composition an antimicrobial mixture as claimed in claim 1 .

18. A process for treating water which comprises incorporating the antimicrobial mixture as claimed in claim 1 into water is chosen from domestic or industrial waters, waters from aquatic media, swimming pool/spa waters, and waters from air-conditioning systems.

19. A continuous or discontinuous water treatment process comprising at least one step of placing a water sample to be treated or a water stream to be treated, said water being chosen from domestic or industrial waters, waters from aquatic media, swimming pool/spa waters, and waters from air-conditioning systems, in contact with the anti

Assignees

• Oreal

Inventors

• Cupferman Sylvie
• Menard-Szczebara Florence
• Galvan Julien

Classifications

• A01N59/16

  Heavy metals; Compounds thereof · CPC title

• A01N37/44

  containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids · CPC title

• A01P1/00

  Disinfectants; Antimicrobial compounds or mixtures thereof · CPC title

• A01N35/02 Primary

  containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals · CPC title