IP Library Granted Patent US 7,847,123
Granted Patent B2
US 7,847,123 · App. 11/939,876 · Granted Dec 7, 2010

Antimicrobial compositions

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Quick Facts
Patent No.
US 7,847,123
App. No.
11/939,876
Granted
Dec 7, 2010
Kind
B2
Abstract

Compounds of the general formula and to the use thereof for controlling microorganisms are provided.

Claims (46)

1. A compound of general formula (I)

wherein R 1 ═CH 3 , R 2 is a direct bond, R 3 ═H, R 4 ═C 8 alkyl, R 5 ═H, and n=0, or wherein R 1 ═CH 3 , R 2 is a direct bond, R 3 ═H, R 4 ═C 8 alkyl, R 5 ═H or acyl, n is 2 to 5, based on the mean value of all oligomers, and AO=—CH 2 CH 2 O—.

2. A method of controlling Gram-positive microorganisms in a cosmetic preparation comprising adding at least one microorganism controlling compound to said cosmetic preparation, said at least one microorganism controlling compound is a compound of general formula Ia

wherein

R 1 =H or a hydrocarbon radical having 1 to 18 carbon atoms,

R 2 =a direct bond or a hydrocarbon radical having 1 to 18 carbon atoms,

R 3 , R 4 =independently of one another, is H or a hydrocarbon radical having 1 to 18 carbon atoms,

R 5 =H or C 1 -C 4 -acyl radical,

AO=at least one radical selected from the group —CH 2 CH 2 O—, —CH 2 CHR 6 O—, —CHR 6 CH 2 O—, and —CH 2 CH 2 OHCH 2 O— where R 6 ═C 1 -C 4 -alkyl,

n=0 to 20, based on the mean value of all oligomers,

with the proviso that R 3 and R 4 are not H at the same time and the sum of the carbon atoms in R 3 and R 4 is not greater than 18 and that the sum of the carbon atoms in R 1 , R 2 , R 3 and R 4 does not exceed 36.

3. The method as claimed in claim 2 , wherein said hydrocarbon of one of R 1 , R 2 , R 3 and R 4 is branched and/or contains multiple bonds and/or hydroxy groups and/or alkyl groups and/or hydroxyalkyl groups.

4. The method as claimed in claim 2 wherein n=0 to 20, R 5 ═H, R 1 ═H or CH 3 , R 2 is a direct bond or a hydrocarbon radical having 1 to 4 carbon atoms which optionally contains hydroxyalkyl groups, R 3 ═H and R 4 ═C 4 -C 12 -alkyl radical.

5. The method as claimed in claim 2 , wherein AO=—CH 2 CH 2 O— and n=2 to 5.

6. The method as claimed in claim 5 wherein said Gram-positive microorganisms are coryneform bacteria.

7. A formulation for the selective control of microorganisms, comprising at least one compound of general formula (Ia)

wherein

R 1 =H or a hydrocarbon radical having 1 to 18 carbon atoms,

R 2 =a direct bond or a hydrocarbon radical having 1 to 18 carbon atoms,

R 3 , R 4 =independently of one another, is H or a hydrocarbon radical having 1 to 18 carbon atoms,

R 5 =H or C 1 -C 4 -acyl radical,

AO=at least one radical selected from the group —CH 2 CH 2 O—, —CH 2 CHR 6 O—, —CHR 6 CH 2 O—, and —CH 2 CH 2 OHCH 2 O— where R 6 ═C 1 -C 4 -alkyl,

n=0 to 20, based on the mean value of all oligomers,

with the proviso that R 3 and R 4 are not H at the same time and the sum of the carbon atoms in R 3 and R 4 is not greater than 18 and that the sum of the carbon atoms in R 1 , R 2 , R 3 and R 4 does not exceed 36.

8. The formulation as claimed in claim 7 , wherein said hydrocarbon of one of R 1 , R 2 , R 3 and R 4 is branched and/or contains multiple bonds and/or hydroxy groups and/or alkyl groups and/or hydroxyalkyl groups.

9. The formulation as claimed in claim 7 , which comprises 0.001 to 10% by weight of at least one compound of said general formula (Ia).

10. The formulation as claimed in claim 7 , which is a deodorant in the form of an aerosol spray, pump spray, roll-on formulation, deodorant stick, W/O or O/W emulsion or wipe.

11. The formulation as claimed in claim 7 , which is an oral hygiene product.

12. A method of combating acne/dandruff comprising applying a formulation including at least one antiacne/antidandruff compound to skin or hair, said at least one antiacne/antidandruff compound is a compound of general formula Ia

wherein

R 1 =H or a hydrocarbon radical having 1 to 18 carbon atoms,

R 2 =a direct bond or a hydrocarbon radical having 1 to 18 carbon atoms,

R 3 , R 4 =independently of one another, is H or a hydrocarbon radical having 1 to 18 carbon atoms,

R 5 =H or C 1 -C 4 -acyl radical,

AO=at least one radical selected from the group —CH 2 CH 2 O—, —CH 2 CHR 6 O—, —CHR 6 CH 2 O—, and —CH 2 CH 2 OHCH 2 O— where R 6 ═C 1 -C 4 -alkyl,

n=0 to 20, based on the mean value of all oligomers,

with the proviso that R 3 and R 4 are not H at the same time and the sum of the carbon atoms in R 3 and R 4 is not greater than 18 and that the sum of the carbon atoms in R 1 , R 2 , R 3 and R 4 does not exceed 36.

13. A method of controlling Gram-positive microorganisms comprising applying a cosmetic preparation to skin, said cosmetic preparation including a compound of general formula (Ia)

wherein

R 1 =H or a hydrocarbon radical having 1 to 18 carbon atoms,

R 2 =a direct bond or a hydrocarbon radical having 1 to 18 carbon atoms,

R 3 , R 4 =independently of one another, is H or a hydrocarbon radical having 1 to 18 carbon atoms,

R 5 =H or C 1 -C 4 -acyl radical,

AO=at least one radical selected from the group —CH 2 CH 2 O—, —CH 2 CHR 6 O—, —CHR 6 CH 2 O—, and —CH 2 CH 2 OHCH 2 O— where R 6 ═C 1 -C 4 -alkyl,

n=0 to 20, based on the mean value of all oligomers,

with the proviso that R 3 and R 4 are not H at the same time and the sum of the carbon atoms in R 3 and R 4 is not greater than 18 and that the sum of the carbon atoms in R 1 , R 2 , R 3 and R 4 does not exceed 36.

Assignments (1)
MERGER Recorded Feb 26, 2014
From: EVONIK GOLDSCHMIDT GMBH
To: EVONIK DEGUSSA GMBH
Reel/Frame 032335/0326 →