Synergistic mixtures of aromatic alcohols and derivatives thereof and tropolone (derivatives)

Patent metadata

Field	Value
Publication number	US-10022310-B2
Application number	US-46176206-A
Country	US
Kind code	B2
Filing date	Aug 1, 2006
Priority date	Jun 17, 2005
Publication date	Jul 17, 2018
Grant date	Jul 17, 2018

Abstract

An antimicrobial mixture comprising or consisting of:
one or more compounds of the formula (I)

their salts or solvates,
wherein R 1 and R 2 in each case independently of one another are chosen from the group consisting of: H, OH, F, Cl, Br and I,
and wherein X in each case denotes:

(CH 2 ) m

where m=1, 2 or 3
or

O CH 2 n

where n=1, 2 or 3
or

O—CH 2 —CH(R 3 )

where R 3 =CH 3 or CH 2 OH
or

(CH 2 —O p CH 2

where p=1 or 2,
wherein in the compound(s) of the formula I
a primary alcohol function CH 2 OH is optionally replaced by a radical which is chosen from the group consisting of CH 2 OR 4 , COOH and COOR 4 and/or
a secondary alcohol function CHOH is optionally replaced by the radical CHOR 4 ,
wherein each R 4 denotes an aliphatic or aromatic radical, independently of the meaning of further radicals, and
one, two or more compounds chosen from the group consisting of the tropolones of the formula (II)

wherein the substituents R 5 , R 6 , R 7 , R 8 , R 9 independently of one another have the following meaning:
H;
linear or branched, saturated or unsaturated, aliphatic hydrocarbon radical having up to 30 C atoms;
OH;
OR 10 , wherein R 10 is a linear or branched, saturated or unsaturated, aliphatic hydrocarbon radical having up to 30 C atoms;
COOH;
COOR 11 , wherein R 11 is a linear or branched, saturated or unsaturated, aliphatic hydrocarbon radical having up to 30 C atoms;
NO 2 ,
NH 2 ,
F, Cl, Br, I.

First claim

We claim:

1. Antimicrobial mixture comprising:
(a) phenoxyethanol

and
(b) tropolone of the formula (II)

wherein the substituents R 5 , R 6 , R 7 , R 8 and R 9 represent H,
constituent (b) is present in an amount in the range of 0.001-10 wt. %, based on the amount of constituent (a), and
compounds (a) and (b) are present in an amount such that an antimicrobial activity of said compounds (a) and (b) is synergistically intensified against Aspergillus niger as shown by a Kull value.

2. An antimicrobial mixture according to claim 1 , wherein constituent (b) is present in an amount in the range of 0.5-4 wt. %, based on the amount of constituent (a).

3. An antimicrobial mixture according to claim 1 , comprising one or more additional constituents (c) selected from the group consisting of (c) 2,4-hexadienoic acid (sorbic acid) and its salts, formaldehyde and paraformaldehyde, 2-hydroxybiphenyl ether and its salts, 2-zinc-sulfidopyridine N-oxide, inorganic sulfites and bisulfites, sodium iodate, chlorobutanolum, 4-ethylmercury-(II)5-amino-1,3-bis(2-hydroxybenzoic acid), its salts and esters, dehydracetic acid, formic acid, 1,6-bis(4-amidino-2-bromophenoxy)-n-hexane and its salts, the sodium salt of ethylmercury-(II)-thiosalicylic acid, phenylmercury and its salts, 10-undecylenic acid and its salts, 5-amino-1,3-bis(2-ethylhexyl)-5-methyl-hexahydropyrimidine, 5-bromo-5-nitro-1,3-dioxane, 2-bromo-2-nitro-1,3-propanediol, N-(4-chlorophenyl)-N′-(3,4-dichlorophenyI)-urea, 4-chloro-m-cresol, 2,4,4′-trichloro-2 1 -hydroxy-diphenyl ether, 4-chloro-3,5-dimethylphenol, 1,1′-methylene-bis(3-(1-hydroxymethyl-2,4-dioximidazolidin-5-yl)urea), poly-(hexamethylenediguanide) hydrochloride, hexamethylenetetramine, 1-(3-chloroallyl)-3,5,7-triaza-1-azonia-adamantane chloride, 1-(4-chlorophenoxy)-1-(1H-imidazol-1-yl)-3,3-dimethyl-2-butanone, 1,3-bis(hydroxymethyl)-5,5-dimethyl-2,4-imidazolidinedione, 1,2-dibromo-2,4-dicyanobutane, benzethonium chloride, 2,2′-methylene-bis(6-bromo-4-chlorophenol), bromochlorophene, mixture of 5-chloro-2-methyl-3(2H)-isothiazolinone and 2-methyl-3(2H)-isothiazolinone with magnesium chloride and magnesium nitrate, 2-benzyl-4-chlorophenol, 3-(4-Chlorphenoxy)-1,2-propanediol (Chlorphenesin), 2-chloroacetamide, chlorhexidine, chlorhexidine acetate, chlorhexidine gluconate, chlorhexidine hydrochloride, N-alkyl(C12-C22)trimethyl-ammonium bromide and chloride, 4,4-dimethyl-1,3-oxazolidine, N-hydroxymethyl-N-(1,3-di(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl)-N′-hydroxy-methylurea, 1,6-bis(4-amidino-phenoxy)-n-hexane and its salts, glutaraldehyde, 5-ethyl-1-aza-3,7-dioxabicyclo(3.3.0)octane, 3-(4-chlorophenoxy)-1,2-propanediol, hyamines, alkyl-(C 8 -C 18 )-dimethyl-benzyl-ammonium chloride, alkyl-(C 8 -C 18 )-dimethyl-benzylammonium bromide, alkyl-(C 8 -C 18 )-dimethyl-benzyl-ammonium saccharinate, benzyl hemiformal, 3-iodo-2-propynyl butylcarbamate, sodium hydroxymethyl-aminoacetate and sodium hydroxymethyl-aminoacetate, imidazolidinylurea, diazolidinylurea, sodium hydroxymethylglycinate, chlorphenesin, DMDM hydantoin, methylchloroisothiazolinone, methylisothiazolinones, branched or unbranched 1,2-alkanediols having 6 to 12 carbon atoms, triclosan, climbazole, octoxyglycerol (ethylhexyl glycerol), Octopirox (1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)-pyridone, 2-aminoethanol), chitosan, totarol, farnesol, geranylacetol, glycerol monolaurate, arylalkyl alcohols (preferably 4-methyl-4-phenyl-2-pentanols, 2,2-dimethyl-3-phenylpropanol), essential oils with antimicrobial properties and isolates from essential oils with antimicrobial properties or single aroma chemicals with antimicrobial activity, and polyglycerol esters, preferably polyglyceryl 3-caprylates.

4. An antimicrobial mixture according to claim 1 , wherein the amount of constituent (a) and/or the amount of constituent (b) in each case considered in itself is not antimicrobially active, but the total amount of constituent (a) and (b) is antimicrobially active.

5. A cosmetic or pharmaceutical formulation or foodstuff comprising the antimicrobial mixture according to claim 1 .

6. A foodstuff according to claim 5 , wherein the amount of constituent (a) and/or the amount of constituent (b) in each case considered in itself is not antimicrobially active, but the total amount of constituents (a) and (b) is antimicrobially active.

7. A method for the preservation or antimicrobial treatment of a perishable product, with the following step:
bringing of the perishable product into contact with an antimicrobially active amount of the mixture according to claim 1 .

8. A method for the cosmetic and/or therapeutic treatment of
(i) microorganisms which cause body odour,
(ii) microorganisms which cause acne and/or
(iii) microorganisms which cause mycoses,
comprising topical application of an antimicrobially active amount of the mixture according to claim 1 .

9. An antimicrobial mixture according to claim 1 , wherein the antimicrobial activity of said compounds (a) and (b) is synergistically intensified against the Aspergillus niger within two days.

10. An antimicrobial mixture according to claim 1 , excluding antimicrobial mixtures comprising or consisting of
(a) one or more branched or unbranched alkanediols having 6-12 carbon atoms,
(b) tropolone, and
(c) one or more preservatives selected from the group consisting of: benzoic acid, its esters and salts, salicylic acid and its salts, 2,4-dichlorobenzyl alcohol, 2-phenoxyethanol, benzyl alcohol, 1-phenoxy-propan-2-ol, 3-(4-chlorophenoxy)-1,2-propanediol and benzyl hemiformal.

Assignees

• Schmaus Gerhard
• Roeding Joachim
• Pillai Ravikumar
• Johncock William
• Symrise Ag

Inventors

• Schmaus Gerhard
• Roeding Joachim
• Pillai Ravikumar
• Johncock William

Classifications

• A61P31/04

  Antibacterial agents · CPC title

• A61K45/06

  Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca · CPC title

• A61Q19/08

  Anti-ageing preparations · CPC title

• A01N35/06

  containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals · CPC title

• A61Q17/005

  Antimicrobial preparations · CPC title