	US 12,256,733 B2
	Antimicrobial mixture containing 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and an acid or silver-based compound, and cosmetic composition containing same
Sylvie Cupferman, Chevilly Larue (FR); Florence Menard-Szczebara, Chevilly Larue (FR); and Julien Galvan, Chevilly Larue (FR)
Assigned to L'OREAL, Paris (FR)
Appl. No. 17/286,872
Filed by L'OREAL, Paris (FR)
PCT Filed Dec. 6, 2019, PCT No. PCT/EP2019/084046 § 371(c)(1), (2) Date Apr. 20, 2021, PCT Pub. No. WO2020/126562, PCT Pub. Date Jun. 25, 2020.
Claims priority of application No. 1873727 (FR), filed on Dec. 21, 2018.
Prior Publication US 2023/0065230 A1, Mar. 2, 2023
Int. Cl. A01N 35/02 (2006.01); A01N 37/44 (2006.01); A01N 59/16 (2006.01); A01P 1/00 (2006.01)

CPC A01N 35/02 (2013.01) [A01N 37/44 (2013.01); A01N 59/16 (2013.01); A01P 1/00 (2021.08)]

20 Claims

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:

R₁R₂NCH₂COO⁻X⁺ (II)

R₁and R₂denoting a hydrogen atom or a hydroxy (C₁-C₄) 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) AgHal₂, with Hal being identical or different; and

c) Ag_xR³₂and also solvates thereof, with

R₃, which may be identical or different, representing a group chosen from:

sulfate;

nitrate;

hydroxy;

(C₁-C₆) alkylcarboxylate in which the (C₁-C₆) 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.