Use of isosorbide monoesters as antimicrobial active substances

Patent metadata

Field	Value
Publication number	US-9730450-B2
Application number	US-201214237039-A
Country	US
Kind code	B2
Filing date	Jul 31, 2012
Priority date	Aug 4, 2011
Publication date	Aug 15, 2017
Grant date	Aug 15, 2017

Abstract

The use of one or more compounds of the formula (I)

in which
R is a straight-chain or branched saturated alkyl group having 5 to 11 carbon atoms or a straight-chain or branched mono- or polyunsaturated alkenyl group having 5 to 11 carbon atoms

as antimicrobially active compound is described.

The use is preferably in cosmetic, dermatological or pharmaceutical compositions, in crop protection formulations, in washing or cleaning compositions or in paints or coatings.

First claim

The invention claimed is:

1. A method for destroying fungus or inhibiting fungal growth, comprising the step of contacting at least one fungi with a composition comprising at least one compound of the formula (I)

in which
R is a straight-chain or branched saturated alkyl group having 5 to 11 carbon atoms or a straight-chain or branched mono- or polyunsaturated alkenyl group having 5 to 11 carbon atoms.

2. The method as claimed in claim 1 , wherein the radical R in formula (I) is a straight-chain saturated alkyl radical having 7 to 9 carbon atoms.

3. The method as claimed in claim 2 , wherein the radical R in formula (I) is a straight-chain saturated alkyl radical having 7 carbon atoms.

4. The method as claimed in claim 1 , wherein the composition further comprises at least one substance selected from the group consisting of sorbitol, sorbitol esters, sorbitan, sorbitan esters, isosorbide, isosorbide diesters and carboxylic acids.

5. The method as claimed in claim 4 , wherein the composition further comprises
I) isosorbide and
II) at least one isosorbide diester of the formula (II)

where R is a straight-chain or branched saturated alkyl group having 5 to 11 carbon atoms or a straight-chain or branched mono- or polyunsaturated alkenyl group having 5 to 11 carbon atoms.

6. The method as claimed in claim 1 , wherein the composition further comprises
I) from 0.05 to 0.7 part by weight of isosorbide and
II) from 0.1 to 1.0 part by weight of the one or more isosorbide diesters of the formula (II),
in each case based on 1.0 part by weight of the at least one compound of the formula (I).

7. The method as claimed in claim 4 , wherein the composition further comprises at least one sorbitan ester of sorbitan and carboxylic acid R a COOH, where R a is a straight-chain or branched saturated alkyl group having 5 to 11 carbon atoms or a straight-chain or branched mono- or polyunsaturated alkenyl group having 5 to 11 carbon atoms, and where the weight ratio of the at least one compound of the formula (I) to the at least one sorbitan ester is from 70:30 to 100:0.

8. The method as claimed in claim 7 , wherein the carboxylic acid R a COOH is selected from the group consisting of caprylic acid.

9. The method as claimed in claim 4 , wherein the hydroxyl value of the mixture of the at least one compound of the formula (I) and the at least one compound selected from the group consisting of sorbitol, sorbitol esters, sorbitan, sorbitan esters, isosorbide, isosorbide diesters and carboxylic acids in the composition is less than or equal to 320.

10. The method as claimed in claim 4 , wherein the composition comprises the at least one compound of the formula (I) in an amount of at least 30% by weight, in each case based on the total weight of the finished composition.

11. The method as claimed in claim 1 for preventing fungal growth in a cosmetic, dermatological or pharmaceutical composition, in a crop protection formulation, in a washing or cleaning composition or in a paint or coating.

12. The method as claimed in claim 11 , wherein the cosmetic, dermatological or pharmaceutical composition, the crop protection formulation, the washing or cleaning composition or the paint or coating comprise the at least one compound of the formula (I) in an amount of from 0.01 to 10.0% by weight, in each case based on the total weight of the finished cosmetic, dermatological or pharmaceutical composition, crop protection formulation, washing or cleaning composition or paint or coating.

13. The method as claimed in claim 11 , wherein the cosmetic, dermatological or pharmaceutical composition, the crop protection formulation, the washing or cleaning composition or the paint or coating is formulated on an aqueous or aqueous-alcoholic basis or are present as emulsion or dispersion.

14. The method as claimed in claim 11 , wherein the cosmetic, dermatological or pharmaceutical composition, the crop protection formulation, the washing or cleaning composition or the paint or coating has a pH of from 2 to 11.

15. The method as claimed in claim 11 , wherein the cosmetic, dermatological or pharmaceutical composition, the crop protection formulation, the washing or cleaning composition or the paint or coating is formulated as an emulsion.

Assignees

• Pilz Maurice Frederic
• Klug Peter
• Scherl Franz-Xaver
• Grohmann Joerg
• Clariant Int Ltd

Inventors

• Pilz Maurice Frederic
• Klug Peter
• Scherl Franz-Xaver
• Grohmann Joerg

Classifications

• A01N43/90 Primary

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title

• A61K31/341

  not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine · CPC title

• A61K31/34

  having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide · CPC title

• A61Q19/00

  Preparations for care of the skin · CPC title

• A61Q17/005

  Antimicrobial preparations · CPC title