Use of vanillin derivatives as preserving agents, preserving process, compounds and composition

Abstract

The present invention relates to the use, in a cosmetic, dermatological or pharmaceutical composition, of at least one compound of formula (I): ##STR00001##
in which: R2 represents a hydrogen atom or a methyl or ethyl radical; R3 represents a linear C1-C12 alkyl radical, optionally substituted with a hydroxyl group; or a linear C2-C12 alkenyl radical, optionally substituted with a hydroxyl group;
as a preserving agent. The invention also relates to certain novel compounds and to the cosmetic, dermatological or pharmaceutical compositions comprising them.

Claims

1. A process for preserving a composition, which comprises incorporating an effective preserving amount into the said composition of a compound of the following formula ##STR00007## wherein said compound is present in an amount of from 0.01% to 5% by weight, relative to the weight of the composition.

2. The process according to claim 1, wherein said compound is present in an amount of from 0.01% to 2.5% by weight, relative to the weight of the composition.

3. The process according to claim 1, wherein the composition does not contain any preserving acting agent in addition to said compound.

4. The process according to claim 1, wherein the composition does not contain a paraben.

5. The process according to claim 1, wherein the composition is in the form of a product for making up the skin of the face, body or lips; an aftershave gel or lotion; a hair-removing cream; a body hygiene composition; a pharmaceutical composition; a solid composition; an aerosol composition also comprising a pressurized propellant; a hair-setting lotion, a hair-styling cream or gel, a dyeing composition, a hair-restructuring lotion, a permanent-wave composition, a lotion or a gel for combating hair loss; or a composition for oro-dental use.

6. The process according to claim 1, wherein the composition comprises a physiologically acceptable medium which comprises at least one ingredient selected from the group consisting of silicone fatty substances selected from the group consisting of silicone oils, gums and waxes; non-silicone fatty substances selected from the group consisting of oils, pastes and waxes of plant, mineral, animal and/or synthetic origin; and wherein the composition optionally further comprises an active cosmetic agent.

7. The process according to claim 1, wherein the composition comprises a physiologically acceptable medium comprising at least one ingredient selected from the group consisting of silicone fatty substances, non-silicone fatty substances, glycols, ketones, thickeners, emulsifiers, surfactants, gelling agents, fragrances, fillers, dyestuffs, moisturizers, vitamins and polymers.

8. The process according to claim 1, wherein said composition comprises at least one aqueous phase and has a pH of 4 to 9.

9. The process according to claim 1, wherein said composition comprises at least one aqueous phase and has a pH of 4 to 7.

10. The process according to claim 1, wherein said composition comprises at least one aqueous phase and has a pH of 5 to 6.

11. The process according to claim 1, which comprises preserving said composition against at least one contaminating agent selected from the group consisting of bacteria, yeast and mould.

12. The process according to claim 5, wherein said body hygiene composition is a shower gel or a shampoo.

13. The process according to claim 5, wherein said solid composition is a soap or a cleansing bar.

14. The process according to claim 1, wherein said composition does not contain any ester having the structure R.sup.1COOR.sup.2 in which R.sup.1 represents a fatty acid residue containing from 8 to 29 carbon atoms and R.sup.2 represents a branched or unbranched hydrocarbon-based chain containing from 3 to 30 carbon atoms.

15. The process according to claim 1, wherein said composition exhibits less than 200 cfu/gram of E. coli, P. aeruginosa, E. faecalis, C. albicans, and/or A. niger after 7 days when inoculated with about 10.sup.6 cfu/gram of the E. coli, P. aeruginosa, E. faecalis, C. albicans, and/or A. niger and maintained at 22° C.±2° C.

16. A process for preserving a composition exposed to at least one of the group consisting of bacteria, yeasts and molds which comprises incorporating an effective preserving amount into the said composition of a compound of the following formula ##STR00008## wherein said compound is present in an amount of from 0.01% to 5% by weight, relative to the weight of the composition.

17. The process according to claim 16, wherein said composition does not contain any ester having the structure R.sup.1COOR.sup.2 in which R.sup.1 represents a fatty acid residue containing from 8 to 29 carbon atoms and R.sup.2 represents a branched or unbranched hydrocarbon-based chain containing from 3 to 30 carbon atoms.

18. The process according to claim 17, wherein said composition exhibits less than 200 cfu/gram of E. coli, P. aeruginosa, E. faecalis, C. albicans, and/or A. niger after 7 days when inoculated with about 10.sup.6 cfu/gram of the E. coli, P. aeruginosa, E. faecalis, C. albicans, and/or A. niger and maintained at 22° C.±2° C.

19. The process according to claim 17, wherein the composition does not contain any preserving acting agent in addition to said compound.

20. The process according to claim 1, wherein said composition exhibits less than 200 cfu/gram of E. coli, P. aeruginosa, E. faecalis, C. albicans, and/or A. niger after 7 days when inoculated with about 10.sup.6 cfu/gram of the E. coli, P. aeruginosa, E. faecalis, C. albicans, and/or A. niger and maintained at 22° C.±2° C.

21. The process according to claim 16, wherein the composition is in the form of a product for making up the skin of the face, body or lips; an aftershave gel or lotion; a hair-removing cream; a body hygiene composition; a pharmaceutical composition; a solid composition; an aerosol composition also comprising a pressurized propellant; a hair-setting lotion, a hair-styling cream or gel, a dyeing composition, a hair-restructuring lotion, a permanent-wave composition, a lotion or a gel for combating hair loss.

22. The process according to claim 1, wherein the composition is in the form of a product for making up the skin of the face, body or lips; an aftershave gel or lotion; a hair-removing cream; a body hygiene composition; a pharmaceutical composition; a solid composition; an aerosol composition also comprising a pressurized propellant; a hair-setting lotion, a hair-styling cream or gel, a dyeing composition, a hair-restructuring lotion, a permanent-wave composition, a lotion or a gel for combating hair loss.

23. The process according to claim 22, wherein said composition does not contain any ester having the structure R.sup.1COOR.sup.2 in which R.sup.1 represents a fatty acid residue containing from 8 to 29 carbon atoms and R.sup.2 represents a branched or unbranched hydrocarbon-based chain containing from 3 to 30 carbon atoms.

Description

EXAMPLE 1

Determination of the Antimicrobial Activity of a Compound According to the Invention

(1) The antimicrobial efficacy of a compound of formula (I) was evaluated via the Challenge Test or artificial contamination method.

(2) Compound Tested:

(3) ##STR00006##

(4) Protocol

(5) The method of the challenge test consists of an artificial contamination of the sample with collection microbial strains (bacteria, yeasts and moulds) and evaluation of the number of revivable microorganisms seven days after the inoculation.

(6) In order to demonstrate the effect of the compounds of formula (I) the antimicrobial activity of a cosmetic formula containing, respectively, 2% of a compound according to the invention was compared with the same formula alone (control), after inoculation with about 10.sup.6 cfu (colony-forming units)/gram of cosmetic formula.

(7) Cosmetic Formula (Weight %)

(8) TABLE-US-00001 sorbitan tristearate (Span 65 V ® from Croda) 0.9% polyethylene glycol stearate (40 OE) 2.0% (Myrj 52 P ® from Croda) glyceryl mono-distearate (36/64)/potassium stearate mixture 3.0% fatty acids of plant origin (53/44/3 stearic acid/ 1.0% palmitic acid/myristic acid) cetyl alcohol 3.8% myristyl myristate 2.0% cyclopentasiloxane 5.0% fillers 0.8% glycerol 3.0% hydrogenated isoparaffin 7.2% white petroleum jelly 4.0% water qs 100%

(9) Microorganism Cultures

(10) 5 pure microorganism cultures are used.

(11) TABLE-US-00002 MICROORGANISMS Subculturing medium T° ATCC Escherichia coli (Ec) Trypto-casein soya 35° C. 8739 Enterococcus faecalis (Ef) Trypto-casein soya 35° C. 33186 Pseudomonas aeruginosa (Pa) Trypto-casein soya 35° C. 19429 Candida albicans (Ca) Sabouraud 35° C. 10231 Aspergillus niger (An) Malt 35° C. 6275 ATCC = American Type Culture Collection

(12) The gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa), gram-positive bacteria (Enterococcus faecalis), yeast (Candida albicans) and mould (Aspergillus niger) are seeded in the subculturing medium, respectively, the day before the inoculation for the bacteria and the yeast, and five days before the inoculation for the mould.

(13) On the day of inoculation: a suspension in Tryptone salt diluent is prepared, respectively, for the bacteria and the yeast, so as to obtain in a spectrophotometer a suspension with an optical density of between 35% and 45% transmitted light at 544 nm; for the mould, the spores are collected by washing the agar with 6 to 7 ml of harvesting solution and the suspension is recovered in a sterile tube or flask.

(14) After homogenizing the microbial suspension, 0.2 ml of inoculum is introduced into each pill bottle (the suspensions are used pure: between 1×10.sup.8 and 3×10.sup.8 cfu per ml) and the microbial suspension in the 20 g of product (=cosmetic formula) is homogenized thoroughly using a spatula.

(15) The content of microorganisms present in the product corresponds after homogenization to a concentration of 10.sup.6 microorganisms per gram of product, i.e. inoculation to 1% of an inoculum containing 10.sup.8 microorganisms per ml. After 7 days of contact time between the microorganisms and the product at 22° C.±2° C. and in darkness, decimal dilutions are performed and the number of revivable microorganisms remaining in the product is counted.

(16) Results

(17) TABLE-US-00003 No. of cfu/gram of product at T7 days Content E. coli P. aeruginosa E. faecalis C. albicans A. niger Compound 2% <200 <200 <200 <200 3.4 × 10.sup.5 <200 cfu: sensitivity threshold of the method

EXAMPLE 2

(18) An emulsion is prepared, comprising (weight %):

(19) TABLE-US-00004 sorbitan tristearate (Span 65 V ® from Croda) 0.9%   polyethylene glycol stearate (40 OE) 2% (Myrj 52 P ® from Croda) glyceryl mono-distearate (36/64)/potassium stearate mixture 3% fatty acids of plant origin (53/44/3 stearic acid/ 1% palmitic acid/myristic acid) glycerol 3% cyclopentasiloxane 5% hydrogenated isoparaffin 7.2%   white petroleum jelly 4% cetyl alcohol 4% myristyl myristate 2% fillers 0.8%   compound tested in Example 1 2% water qs 100%

EXAMPLE 3

(20) An O/W emulsion is prepared, comprising (weight %):

(21) TABLE-US-00005 sodium hydroxide 0.03% liquid petroleum jelly   10% 2-ethylhexyl palmitate   10% acrylic acid/stearyl methacrylate copolymer  0.1% polymerized in an ethyl acetate/cyclohexane mixture glycerol   5% mixture of cetylstearyl glucoside and of cetyl and stearyl 2.45% alcohols (12/46/42) compound tested in Example 1   2% microbiologically clean deionized water qs 100%

EXAMPLE 4

(22) A lotion is prepared, comprising (weight %):

(23) TABLE-US-00006 allantoin 0.05% sodium chloride 0.09% citric acid qs pH 7 ± 0.2 cornflower water   1% hexylene glycol (2-methyl-2,4-pentanediol)   1% glycerol   5% sodium N-cocoylamidoethyl-N-ethoxycarboxymethyl  1.1% glycinate sodium/magnesium lauryl ether sulfate (80/20) 40 OE 0.45% (52% SM) compound tested in Example 1  1.5% microbiologically clean deionized water qs 100%