Synergistic mixtures of 1,2-alkane diols

• US 7,582,681 B2
• Filed: 10/17/2002
• Issued: 09/01/2009
• Est. Priority Date: 02/19/2002
• Status: Expired due to Term

• Current Assignee: Symrise AG
• Original Assignee: Symrise Gmbh & Co. Kg (Symrise AG)
• Inventors: Joppe, Holger, Schmaus, Gerhard, Lange, Sabine
• Primary Examiner(s): CHONG, YONG SOO
• Application Number:
  US10/502,132
• Publication Number:
  US 20050222276A1
• Time in Patent Office: 2,511 Days
• Field of Search: 424/44, 514/564, 514/724
• US Class Current: 514/738
• CPC Class Codes: A01N 2300/00 Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
• CPC Class Codes: A01N 31/02 Acyclic compounds
• CPC Class Codes: A01N 37/34 Nitriles
• CPC Class Codes: A01N 39/00 Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or , e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
• CPC Class Codes: A61K 2800/524 Preservatives
• CPC Class Codes: A61K 2800/59 Mixtures
• CPC Class Codes: A61K 8/34 Alcohols
• CPC Class Codes: A61K 8/345 containing more than one hydroxy group
• CPC Class Codes: A61P 31/10 Antimycotics
• CPC Class Codes: A61Q 15/00 Anti-perspirants or body deodorants deodorisation of air A61L9/00
• CPC Class Codes: A61Q 17/005 Antimicrobial preparations
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin

Abstract

The use of mixtures of two, three or more straight-chain 1,2-alkanediols, the chains lengths of which (i) are different and (ii) in each case are in the range of 5 to 10 C atoms, as antimicrobial active compounds is described. Compared with the pure 1,2-alkanediols, the mixtures have a synergistically intensified action.

Claims

1. An antimicrobial composition, comprising an antimicrobial effective amount of a mixture of 1,2-alkanediols consisting of two or more straight chain 1,2-alkanediols having chain lengths that (i) are different and (ii) in each case are in the range of 5 to 10 C atoms, wherein said mixture of 1,2-alkanediols exhibits an antimicrobial effect characterized by a Kull value of less than 1.

2. The antimicrobial composition according to claim 1, wherein the proportions of the said diols in the mixture are set such that a Kull value of 0.83 or less for the antimicrobial effect exhibited by said mixture of 1,2-alkanediols results.

3. The antimicrobial composition according to claim 1, wherein the mixture contains 1,2-hexanediol and one, two or three further straight-chain 1,2-alkanediols, the chain length of which in each case is in the range of 5 to 10 C atoms.

5. The antimicrobial composition according to claim 1, wherein the proportion of each individual diol is in the range of 20 to 80% (m/m) based on the total mass of the mixture of the diols.

8. An antimicrobial composition according to claim 1, further comprising an antimicrobial active compound in an amount at which an antimicrobial action of a mixture of said antimicrobial active compound and said mixture of 1,2-alkanediols is synergistically intensified, the further antimicrobial active compound not being a straight-chain 1,2-alkanediol.

21. The antimicrobial composition of claim 1, wherein said antimicrobial composition comprises said mixture of 1,2-alkanediols in an amount between 0.01 and 30% (m/m) by mass of said antimicrobial composition.

22. The antimicrobial composition of claim 1, wherein said antimicrobial composition comprises said mixture of 1,2-alkanediols in an amount between 0.1 and 5% (m/m) by mass of said antimicrobial composition.

4. An antimicrobial composition comprising an antimicrobial effective amount of a mixture of 1,2-alkanediols consisting of at least one of:

(a) 1,2-hexanediol and 1,2-octanediol,

(b) 1,2-hexanediol and 1,2-decanediol,

(c) 1,2-pentanediol, 1,2-hexanediol and 1,2-octanediol,

(d) 1,2-hexanediol, 1,2-octanediol and 1,2-decanediol and

(e) 1,2-pentanediol, 1,2-hexanediol and 1,2-decanediol

as antimicrobial active compounds, the proportions of the said diols in the mixture of 1,2-alkanediols being set such that a Kull value of less than 1.0 for the antimicrobial effect exhibited by said mixture of 1,2-alkanediols results.

19. An antimicrobial composition as in claim 4, wherein said 1,2-hexanediol and 1,2-octanediol are present in a ratio of 1:

1.

20. An antimicrobial composition as in claim 4, wherein said 1,2-hexanediol and 1,2-octanediol are present in a ratio of 2:

1.

6. An antimicrobial composition comprising an antimicrobial effective amount of a mixture of 1,2-alkanediols consisting of two or more straight chain 1,2-alkanediols having chain lengths of which (i) are different and (ii) are in the range of 5 to 10 C atoms, wherein the proportions of said diols in the mixture of 1,2-alkanediols are set such that a Kull value of less than 1.0 for the antimicrobial effect exhibited by said mixture of 1,2-alkanediols results for at least one of:

(a) a cosmetic treatment of microorganisms causing body odour,

(b) a cosmetic treatment of microorganisms causing acne,

(c) a cosmetic treatment of microorganisms causing mycoses,

(d) a treatment of microorganisms on or in inanimate material and

(e) preservation of a perishable product.

7. An antimicrobially active pharmaceutical composition consisting of an antimicrobial effective amount of a mixture of 1,2-alkanediols consisting of two or more straight chain 1,2-alkanediols having chain lengths of which (i) are different and (ii) are in the range of 5 to 10 C atoms, wherein the proportions of the said diols in the mixture of 1,2-alkanediols are such that said mixture of 1,2 alkanediols exhibits an antimicrobial effect characterized by a Kull value of less than 1.0.

9. An antimicrobial composition, comprising:

(a) as antimicrobial active compound, a mixture of two, three or more straight-chain 1,2-alkanediols, the chain lengths of which (i) are different and (ii) in each case are in the range of 5 to 10 C atoms, and

(b) an excipient compatible with the said mixture, wherein the proportions of the said diols in the mixture are set such that a Kull value of less than 1.0 for the antimicrobial effect exhibited by said mixture of 1,2-alkanediols results.

10. An antimicrobial composition, comprising

(a) an antimicrobial effective amount of a mixture of two, three or more straight-chain 1,2-alkanediols, the chain lengths of which (i) are different and (ii) in each case are in the range of 5 to 10 C atoms, and

(b) a preservative other than straight-chain 1,2-alkanediols, wherein the proportions of the said diols in the mixture are set such that a Kull value of less than 1.0 for the antimicrobial effect exhibited by said mixture of 1,2-alkanediols results.

11. An antimicrobial composition as in claim 10, wherein said preservative (b) is selected from the group consisting of benzoic acid and the esters and salts thereof, propionic acid and salts thereof, salicylic acid and salts thereof, 2,4-hexanoic acid and salts thereof, formaldehyde and paraformaldehyde, 2-hydroxybiphenyl ether and salts thereof, 2-zincsulphidopyridine-N-oxide, inorganic sulphites and bisulphites, sodium iodate, chlorobutanolum, 4-ethylmercury-(I1)-5-amino-1,3-bis(2-hydroxy)benzoic acid and salts and esters thereof, dehydraccetic acid, formic acid, 1,6-bis(4-amidino-2-bromophenoxy)-n-hexane and salts thereof, the sodium salt of ethylmercury-(II)-thiosalicylic acid, phenylmercury and salts thereof, 10-undecylenic acid and salts thereof, 5-amino-1,3-bis(2-ethylhexyl)-5-methyl-hexahydropyrimidine, 5-bromo-5-nitro-1,3-dioxane, 2-bromo-2-nitro-1,3-propanediol, 2,4-dichlorobenzyl alcohol, N-(4-chlorophenyl)-N′

-(3,4-dichlorophenyl)-urea, 4-chloro-m-cresol, 2,4,4′

-trichloro-2′

-hydroxy-diphenyl ether, 4-chloro-3,5-dimethylphenol, 1,1′

-methylene-bis(3-(1-hydroxymethyl-2,4-dioximidazolidin-5-yl)urea), poly-(hexamethylene diguanide) hydrochloride, 2-phenoxyethanol, hexamethylentetramine, 1-(3-chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride, 1(4-chlorphenoxy)-1(1H-imidazol-1-yl)-3,3-dimethyl-2-butanone, 1,3-bis-(hydroxy-methyl)-5,5-dimethyl-2,4-imidazolidinedione, benzyl alcohol, octopirox, 1,2-dibromo-2,4-dicyanobutane, 2,2′

-methylene-bis(6-bromo-4-chloro-phenol), bromo-chlorophene, 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, 2-chloracetamide, chlorhexidine, chlorhexidine acetate, chlorhexidine gluconate, chlorhexidine hydrochloride, 1-phenoxy-propan-2-ol, 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-methyl urea, 1,6-bis(4-amidino-phenoxy)-n-hexane and salts thereof, glutaraldehyde 5-ethyl-1-aza-3,7-dioxabicyclo(3.3.0)octane, 3-(4-chlorphenoxy)-1,2-propanediol, hyamine, alkyl-(C₈-C₁₈)-dimethyl-benzylammonium chloride, alkyl-(C₈-C₁₈)-dimethyl-benzyl ammonium bromide, alkyl-(C₈-C₁₈)-dimethyl-benzyl ammonium saccharinate, benzylbemiformal, 3-iodo-2-propinylbutyl carbamate, sodium hydroxymethyl-aminoacetate or sodium hydroxymethyl-aminoacetate.

12. An antimicrobial composition as in claim 11, wherein said preservative (b) is 1,2-dibromo-2,4-dicyanobutane.

13. An antimicrobial composition as in claim 11, wherein said preservative (b) is 2-phenoxyethanol.

14. An antimicrobial composition as in claim 10, wherein said preservative (b) is 3-iodo-2-propinyl-butyl carbamate.

15. An antimicrobial composition as in claim 11, wherein said mixture (a) comprises 1,2-hexanediol or 1,2-octanediol.

16. An antimicrobial composition as in claim 10, wherein said mixture of straight-chain 1,2-alkanediols comprises 1,2-hexanediol and 1,2-octanediol.

17. An antimicrobial composition as in claim 10, further comprising a preservative.

18. An antimicrobial composition as in claim 17, wherein said preservative is 3-iodo-2-propinyl-butyl carbamate.