AU662165B2

AU662165B2 - Ceramide and/or glycoceramide-based cationic dispersions

Info

Publication number: AU662165B2
Application number: AU24347/92A
Authority: AU
Inventors: Daniele Cauwet; Claude Dubief
Original assignee: LOreal SA
Current assignee: LOreal SA
Priority date: 1991-08-01
Filing date: 1992-07-30
Publication date: 1995-08-24
Anticipated expiration: 2012-07-30
Also published as: CA2092990C; ES2078751T3; FR2679770B1; JP3576165B2; FR2679770A1; WO1993002656A1; DE69205561D1; ATE129142T1; EP0551498B1; DE69205561T2; JPH06502660A; EP0551498A1; AU2434792A; CA2092990A1

Abstract

Cationic dispersion containing at least: 1) a ceramide or glycoceramide or a blend of natural or synthetic ceramides and/or glycoceramides of the formula (I) in which R1? is a C14?-C30? alkyl; R2? is hydrogen, (glycosyl)n?, (galactosyl)m? or sulphogalactosyl; n is 1 to 4, m is 1 to 8; R3? is a C15?-C26? hydrocarbonated radical or a C15?-C26? $g(a)-hydroxyalkyl in the case of natural ceramides and/or glycoceramides; 2) a compound of the formula (II) in which X is an anion and a) R4?, R5?, R6? are a C1?-C4? alkyl, R7? is a C22? alkyl, or b) R4? and R5? are a C1?-C4? alkyl and (i) R6? and R7? are a C10?-C22? alkyl; or (ii) R6? is a C22? alkyl, R7? is benzyl; or c) R4? is a C1?-C4? alkyl, R5? is an (alkyl and/or alkenyl)amidoethyl; R6? and R7? are 4,5-dihydroimidazole substituted in position 2 by a C13?-C21? alkyl and/or alkenyl.

Description

OPT DATE 02/03/93 APPLN. ID 24347/92 111III 11 1111III AOJP DATE 13/05/93 PCT NUMBER PCT/FR92/00746 111HhililI DEMANDE INTERNATIONALE k'UtLIUt tN VtKIU LUU IKAIL t utiJ1i CIN WvIIAr u L13 D\LvYL~fS (PCT) i (51) Classification internationale des brevets 5 Num~ro de publication internationale: WO 93/02656 A61K 7/06, 7/48 Al (43) Date de publication internationale: 18 f~vrier 1993 (18.02.93) (21) Num~ro de la demande internationale: PCT/FR92/00746 (81) Etats d~sign~s: AU, CA, JP, US, brevet europ~en (AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LU, MC, NL, SE).

j(22) Date de dipfit international: 30 juillet 1992 (30.07.92) Publiie Donn~es relatives A la prioriti: Avec rapport de recherche internationale.

91/09824 1 eraoii 1991 (01.08.9 1) FR (71) D~posant (pour tous les Etats d~sign&s sauf US): L'OREAL [FR/FR]; 14, rue Royale, F-75008 Paris (FR).

(72) Inventeurs; et Inventeurs/D~posants (US seulement) DUBIEF, Claude [FR/FR]; 9, rue Edmond-Rostand, F-78150 Le-Chesnay CAUWET, Dani~le [FR/FR]; 53, rue de Charonne, F-75011I Paris (FR).

(74)Mandataire: BUREAU D.A. CASALONGA JOSSE; 8, avenue Percier, F-75008 Paris (FR).

(54) Title: CERAMIDE AND/OR GLYCOCERAMIDE-BASED CATIONIC DISPERSIONS (54)Titre: DISPERSIONS CATIONIQUES A BASE DE CERAMIDES ET/OU DE GLYCOCERAMIDES RSCHQH jH CH 2

OR

2 r=1 0 (G)

R

5 (57) Abstract Cat ionic dispersion containing at least: 1) a ceramide or glycoceramide or a blend of natural or synthetic ceramides and/or glycoceramides of the formula in which R, is a C 14

-C

30 alkyl; R 2 is hydrogen, (glycosyl)n, (galactosyl)m or suiphogalactosyl; n is I to 4, m is 1 to 8; R 3 is a C 15

-C

2 6 hydrocarbonated radical or a C 15

-C

26 a-hydroxyalkyl in the case of natural ceramides and/or glycoceramides; 2) a compound of the formula (II) in which X is an anion and a) R 4

R

5

R

6 are a C 1

-C

4 alkyl, R 7 is a C 22 alkyl, orb) R 4 and R 5 are a C 1

-C

4 alkyl and R 6 and R 7 are a C 10

-C

22 alkyl;. or (ii) R 6 is a C 22 alkyl, R 7 is benzyl; or c) R 4 is a C 1

-C

4 alkyl, R 5 is an (alkyl and/or alkenyl)amidoethyl; R 6 and R 7 are 4,5-dihydroimidazole substituted in position 2 by a C 13

-C

21 alkyl and/or alkenyl.

(57) Abrgi Dispersion cationique contenant au momns 1) un c~ramide ou glycoc~ramide ou un m~lange de c~ramides et/ou de glycoc&ramides, naturels ou synth~tiques de formule o6i R, d~signe alkyle en C 14

-C

3 o, R 2 d~signe hydrog~ne, (glycosyle)n, (galactosyle)m ou sulfogalactosyle, n vaut 1 A 4, m vaut 1 A 8. R 3 d~signe un radical hydrocarbon6 en C 15

-C

26 ou ct-hydroxyalkyle en

C

15

-C

26 dans le cas des c~ramides et/ou glycoc~ramides naturels; 2) un compos6 de formule (II) o6~ X est un anion et a R 4

R

5

R

6 d&signent alkyle en Cl-C 4

R

7 alkyle en C 22 ou b) R 4 et R 5 d~signent alkyle en C 1

-C

4 et: R 6 et R 7 d~signent alkyle en C I -C 22 OU (ii) R16 d~signe alkyle en C 22

R

7 d~signe benzyle; ou c) R14 d6signe alkyle en C I-C 4

R

5 d~signe (alkyl et/ou alc~nyl)amido~thyle; R 6 et R 7 d~signe 4,5-dihydroimidazole substitu6 en position 2 par un alkyle et/ou alc~nyle en C3C1

I,

I-nl. Cationic dispersions based on ceramides and/or I_-r glycoceramides.

The present invention relates to catonic dispersions for treating the hair or the skin, to cosmetic compositions containing them and to their cosmetic applications.

It is well known that the hair is sensitized or weakened to various degrees by the action of atmospheric agents, and by the action of various hair treatments such as permanent waves, hair straightening, dyeing or bleaching. The hair then becomes difficult to disentangle and to style. Moreover, it becomes rough to the touch.

To facilitate disentangling and to improve its softness to the touch, cationic surface-active agents are commonly used. These surface-active agents unfortunately have a tendency to make the hair lank and to give it a greasy appearance. This phenomenon becomes more marked, the finer the hair that is treated.

Ceramides have already been proposed in hair compositions. Due to their insolubility in aqueous media, they have until now often been used in formulations based on anionic and/or nonionic surface-active agents.

The Applicant company has observed that emulsions or solutions based on ceramides did not make it possible to obtain good hair-disentangling properties.

The Applicant company has discovered, surprisingly, that by using aqueous dispersions based on ceramides and/or glycoceramides combined with specific cationic surface-active agents, the disentangling of hair was substantially improved without making the hair lank or greasy, while obtaining an even smoothing and sheathing from the root to the tip of the hairs.

The dispersions, according to the invention, also make it possible to reduce the wettability of the hair and thus to achieve faster drying.

The cationic dispersions according to the invention are particularly suitable for treating sensitized rAx hair and fine hair. They are particularly stable.

1 1- r. ,i 2 The Applicant company has also observed that the cationic dispersions of the invention exhibited entirely satisfactory cosmetic properties with respect to the skin and could be applied for treating and caring for the skin.

The subject of the present invention is a cationic dispersion based on ceramides and/or glycoceramides combined with specific cationic surface-active agents.

Another subject relates to cosmetic compositions, containing these dispersions, for treating the hair or the skin.

A treatment having the effect of improving the esthetic appearance of the hair or the skin is called "cosmetic treatment".

Another subject relates to processes for cosmetic treatments using the compositions of the invention.

Other subjects of the invention will appear in the light of the description and examples which follow.

The cationic dispersions of the invention are characterized in that they contain in an aqueous medium: 1) at least one natural or synthetic ceramide or glycoceramide, or a mixture of natural or synthetic ceramides and/or glycoceramides of formula: R CHOH FH CHOR 2

(I)

0 R1 in which: RI denotes a saturated or unsaturated, linear or branched alkyl radical derived from C 14

-C

30 fatty acids, it being possible for the said radical to be substituted by a hydroxyl group in the a position or a hydroxyl group in the w position esterified by a saturated or unsaturated,

C

16

-C

30 fatty acid;

R

2 denotes a hydrogen or a (glycosyl)n -(galactosyl)m or @sA sulfogalactosyl radical, where N 0; 3 n is an integer ranging from 1 to 4, and n is an integer ranging from 1 to 4, and m is an integer ranging from 1 to 8;

R

3 denotes a C 15

-C

2 hydrocarbon radical, saturated or unsaturated in the a position, which can be substituted by one or a number of C 1

-C

14 alkyl radicals; in the case of natural ceramides or glyceramides [sic], R 3 can also denote a C 15

-C

26 a-hydroxyalkyl radical, the hydroxyl group optionally being esterified by a C 1

-C

30 a-hydroxy acid; and 2) at least one cationic surface-active agent of formula:

R

R R 6 in which X denotes an anion and: a) R 4 Rs and R 6 which are identical or different, denote a C 1

-C

4 alkyl radical; R 7 denotes a C 22 alkyl radical; or b) R 4 and R 5 are C 1

-C

4 alkyl radicals, which are identical or different; and

R

6 and R 7 are CI 0

-C

22 alkyl radicals, which are identical or different, with the proviso that the total number of carbon atoms of R 6 and R 7 is greater than or equal to 20; it being possible for the alkyl radical to be interrupted by an ester group and/or an amido group; or (ii) the radical R 7 denotes a benzyl group and R 6 a

C

22 alkyl radical; or c) R 4 denotes a C 1

-C

4 alkyl radical; Rs denotes an (alkyl and/or alkenyl)amidoethyl radical, in which the alkyl and/or alkenyl radical is

C

13

-C

21

R

6 and R 7 form, together with the nitrogen to which they are bonded, a 4,5-dihydroimidazole heterocycle substituted in position 2 by a C 1 3-C, 2 alkyl and/or alkenyl radical.

-1i- 7 I I2

I

4

I

In the formula (II) as defined above, the anion X preferably denotes chlorine or CH 3 OSO3-, and R 4 preferably denotes methyl.

The ceramides and/or glycoceramides/cationic surface-active agents ratio by weight is preferably less than or equal to 2.

The ceramides and/or glycoceramides of formula are used alone or as mixtures. They are prepared from natural extracts originating from pig skin, bovine brain, eggs, blood cells, plants and the like. They are described in the patents JA-86/260,008 and JA-87/120,308 and in the application EP-0,278,505.

Among the compounds of formula as defined above, there are preferably used those for which:

R

1 denotes a saturated or unsaturated alkyl derived from a C,,-C 22 fatty acid;

R

2 denotes hydrogen;

R

3 denotes a saturated linear C15 radical, Such compounds are, for example: N-linoleoyldihydrosphingosine N-oleoyldihydrosphingosine N-palmitoyldihydrosphingosine N-stearoyldihydrosphingosine N-behenoyldihydrosphingosine, or mixtures of these compounds.

There are also preferably used those for which: R, denotes a saturated or unsaturated alkyl radical derived from a fatty acid;

R

2 denotes galactosyl or sulfogalactosyl; and R, denotes -CH=CH-(CH 2

),-CH

3 There may be mentioned the product consisting of a mixture of these compounds, sold under the commercial name Glycocer by the Company Waitaki International Biosciences.

The cationic surface-active agents of formula (II) of the invention are preferably chosen from the group formed by: a) the tetraalkylammonium halides, such as behenyltrimethylammonium chloride or dimethyldistearylammonium chloride.

b) a quaternary ammonium salt of formula (III): 0 CH3 R-C-NH-CH2-CHZ-N CH, CH 3

OSO

3

R

in which R denotes a mixture of C,-C 21 alkenyl and/or I alkyl radicals derived from tallow fatty acids, such as, for example, the products sold under the commercial name Rewoquat (W 75, W 75 PG, W 90, W 90 DPG, W 1599, W 75 H) by the Company Rewo.

c) stearamidopropyldimethyl(myristylacetate)ammonium chloride such as, for example, the product sold under the name Ceraphyl 70 by the Company Mallinckrodt.

The cationic dispersions in accordance with the invention can be prepared by forming a paste of the cationic surface-active agent and of the ceramide, followed by melting the mixture at a temperature of approximately 80 0 C and then adding hot water (80-90 0

C)

with vigorous stirring using an Ultraturrax.

In the dispersions according to the invention, the ceramide and/or glycoceramide compound of formula (I) is present in concentrations between 0.01 and 15% by weight, preferably between 0.05 and 10% by weight, with respect to the total weight of the dispersion and the cationic surface-active agent of formula (II) is present in concentrations of 0.01 to 15% by weight, and preferably of 0.05 to 10% by weight, with respect to the total weight of the dispersion.

The cationic dispersions according to the inven- 3 1 0 tion can be incorporated in cosmetic compositions for -6treating the hair or the skin, in order to be used in particular as shampoos, as rinsable products applied before or after shampooing, before or after dyeing or bleaching, before or after a permanent wave or hair straightening or between their two stages of reduction and oxidation; as non-rinsed hair care products, to be applied after a shampoo; as hair setting or blow drying lotions; as skin care compositions.

These cosmetic compositions then contain the ceramides and/or glycoceramides of formula in proportions between 0.005 and 15% by weight, and preferably between 0.01 and 10%, with respect to the total weight of the composition and the cationic surface-active agent of formula (II) in proportions between 0.01 and 15% by weight, and preferably between 0.05 and 10% by weight, with respect to the total weight of the composition.

The cosmetic compositions according to the invention have a pH generally between 2 and 9 and more particularly between 3 and 7.

These compositions can be provided in the form of more or less thick liquids, of gels, of creams, of aerosol foams or of sprays.

The compositions can also contain, in addition to the dispersion defined above, viscosity regulating agents, such as electrolytes, hydrotropic agents or thickeners. Among these compounds, there may be especially mentioned: sodium chloride, sodium xylenesulfonate, the cellulose derivatives, such as for example carboxy- i methylcellulose and hydroxypropylcellulose, the xanthan gums, guar gum, hydroxypropylated guar gums and scleroglucans.

These viscosity regulating agents are used in proportions ranging up to 15% by weight with respect to the total weight of the composition and preferably below 6%.

The compositions in accordance with the invention can optionally additionally contain other agents having Athe effect of improving the cosmetic properties of the 22 U

NI,

7 hair or the skin, provided that they do not detrimentally affect the stability of the compositions, such as anionic, nonionic or cationic polymers or quaternized or non-quaternized proteins and silicones.

The cationic, nonionic or anionic polymers, the quaternized or non-quaternized proteins and the silicones are used in the cosmetic compositions of the invention in proportions between 0.05 and and preferably between 0.1 and with respect to the total weight of the composition.

The compositions according to the invention can also contain various adjuvants usually used in cosmetics, such as fragrances, preserving agents, sequestering agents, foam stabilizing agents, propellants, dyes, acidifying or basifying agents and other adjuvants, depending upon the use envisaged.

Another subject of the invention consists of a process for cosmetic treatment of the hair or the skin comprising the application of a composition according to the invention, it being possible for this application to be optionally followed by a rinsing.

The examples which follow are used to illustrate L the invention without, however, limiting it.

EXAMPLE 1 A dispersion having the following composition is Sprepared: N-oleoyldihydrosphingosine of formula: 2 g

R

3

-CHOH-CH-CH

2

OH

I

in which:

R

3

C

15

H

31 R C 17

H

33 Dimethyldistearylammonium chloride 2 g A i Fragrance, preserving agent qs 8 HC1 qs pH 4 Water qs 100 g This cationic dispersion is applied to wet hair after a simple shampoo or a shampoc following upon a hair coloring. After rinsing with water, the wet hair is uniformly smooth and disen:-.ngles very evenly from the root to the tip.

After drying, it is smooth and light and the hair style has excellent form retention.

-0 EXAMPLE 2 A dispersion having the following composition is prepared: Ceramide of Example 1 Behenyltrimethylammonium chloride containing 80% of AM Fragrance, preserving agent q.

HC1 qs pH 4 0.5 g 2 g AM Water qs 100 g This cationic dispersion is applied to the hair as in Example 1, the same results being obtained.

EXAMPLE 3 A dispersion having the following composition is prepared: Ceramide of Example 1 Quaternary ammonium salt of formula (II) sold under the name Rewoquat W 75 PG containing 75% of AM by the company Rewo Triethanolamine qs pH 6 Fragrance, preserving agent qs 0.5 g 2 g AM Water qs 100 g This cationic dispersion is applied to hair which has been subjected to a reduction: 1st stage of a permanent wave. After rinsing, the oxidation stage of the permanent wave is carried out. The hair when wet and when dry exhibits the same advantages as those described in Example 1.

I

i 9 EXAMPLE 4 A dispersion having the following composition is prepared: Dimethyldistearylammonium chloride Ceramide of Example 1 Stearyl alcohol Cetyl alcohol Mixture of cetearyl alcohol and of cetearyl alcohol oxyethylenated by 33 moles of ethylene oxide Triethanolamine qs pH 7 0.7 g 1.4 g 1.4 g 1.4 g 3.6 g Water qs 100 g This cationic dispersion is applied to wet hair which has been subjected to a permanent wave, that is to say after the oxidation stage. After rinsing with water, the hair when wet and when dry the same advantages as in Example 1.

EXAMPLE A dispersion having the following composition is prepared: Ceramide of Example 1 Stearamidopropyldimethyl(myristylacetate)ammonium chloride sold under the name Ceraphyl 70 by the company Mallinckrodt Spontaneous pH Water qs 1 2 g 2 g 00 g This cationic dispersion is applied to hair which has been subjected to bleaching. After rinsing, the hair when wet and when dry exhibits the same advantages as in Example 1.

EXAMPLE 6 A dispersion having the following composition is prepared: N-Behenoyldihydrosphingosine of formula: 0.5 g i 10 in which: R, R21R43

R

3

C

15

H

31 -Dimethyldistearylammonium chloride Preserving agent qs -Spontaneous pH 5 g Water qs 100 g This cationic dispersion is applied to wet hair, after shampooing. Without rinsing the hair, it is dried and then styled. The hair is uniformly smooth, light, sheathed and easy to disentangle from the root to the tip.

EXAMPLE 7 A dispersion having the following composition is prepared: Glycoceramide containing 42% of AM, sold under the name Glycocer by the Company Waitaki International Biosciences 0.1 g AM Collagen hydrolysate quaternized by cocoylamidopropyldimethylamine, containing 30% of AM and sold under the name Lexein QX 3000 by the Company Aqualon 0.3 g AM Quaternary ammonium salt of formula (III), containing 75% of AM and sold under the name Rewoquat W 75 PG by the Company Rewo 0.3 g AM Hydroxyethylcellulose 0.4 g Preserving agent qs Spontaneous pH Water qs 100 g This cationic dispersion is applied to washed and wet hair, optionally wound around rollers. Without rinsing the hair, it is dried. The hair exhibits the same advantages as in Example 6.

EXAMPLE 8 A dispersion having the following composition is prepared: Ceramide of Example 1 Dimethyldistearylammonium chloride 0.5 g 5 g

I

11 Polydimethylsiloxane sold under the name Silbione oil 47 V 50 by the Company Rhine-Poulenc 0.1 g -Preservative qs Spontaneous pH Water qs 100 g This cationic dispersion is applied to clean, wet hair. After rinsing with water, the hair when wet and when dry exhibits the same advantages as in Example 1.

EXAMPLE 9 A dispersion of the following composition is prepared: N-Behenoyldihydrosphingosine of formula: 0.01 g

R

3 -CHOH- HCH2OH

NH

=0

R

1 in which: R, C 21 H43

R

3

C

15

H

31 Quaternary ammonium salt of formula (III), containing 75% of AM and sold under the name Rewoquat W 75 PG by the Company Rewo 0.5 g AM Preserving agent qs HC1 qs pH Water qs 100 g This cationic dispersion is applied to wet hair, after a shampoo. Without rinsing the hair, it is dried and then styled. The hair exhibits the same advantages as in Example 6.

EXAMPLE A following composition for the bath or the shower is prepared: Glycoceramide containing 42% of AM, sold under the name Glycocer by the Company A /Waitaki International Biosciences 0.2 g AM r

I

lr I 12 -Behenyltrimethylammonium chloride Sodium salt of sulfated oxyethylenated lauryl alcohol, sold under the name Empicol ESB/3FL by the Company Marchon 3 Ether carboxylic acid polyoxyethylenated with 10 moles of ethylene oxide, sold under the name Akypo RLM 100 by the Company Chem Y, containing 90% of AM -(Cocoylamidopropyl)hydroxypropylsulfobetaine containing 50% of AM, sold under the name Amonyl 675 SB by the Company Seppic -Fragrance qs Water qs 10 ).63 g 0.0 g 2.3 g AM 4.8 g AM 0.0 g This shampoo for the bath or the shower has a very soft foam and imparts softness to the skin.

A

4,, L I ~I

Claims

1. Cationic dispersion for the treatment and care of the hair and the skin, characterized in that it contains in an aqueous medium: 1) at least one natural or synthetic ceramide or glycoceramide, or a mixture of natural or synthetic ceramides and/or glycoceramides of the following formula: R 3 CHOH CH2OR, (I) RI in which: R z denotes a saturated or unsaturated, linear or branched alkyl radical derived from C 14 -C 30 fatty acids, it being possible for the said radical to be substituted by a hydroxyl group in the a position or a hydroxyl group in the w position esterified by a saturated or unsaturated, C 1 6 -C 30 fatty acid; R 2 denotes a hydrogen or a (glycosyl)n, -(galactosyl)m or sulfogalactosyl radical, where n is an integer ranging from 1 to 4, and m is an integer ranging from 1 to 8; R 3 denotes a C 1 -C 2 hydrocarbon radical, saturated or unsaturated in the a position, which can be substituted by one or a number of C 1 -C, 1 alkyl radicals; in the case of natural ceramides or glyceramides [sic], R 3 can also denote a Cs 1 -C 2 a-hydroxyalkyl radical, the hydroxyl group optionally being esterified by a C 16 -C 30 a-hydroxy acid; and 2) at least one cationic surface-active agent of formula: RR7 (II) RP R 6 S in which X denotes an anion and: EN* 5r 1 z. '4 1 1. 14 a) R 4 Rs and R 6 which are identical or different, denote a C 1 -C 4 alkyl radical; R 7 denotes a C 22 alkyl radical; or b) R 4 and R 5 are C 1 -C 4 alkyl radicals, which are identical or different; and R 6 and R 7 are C 10 -C 22 alkyl radicals, which are identical or different, with the proviso that the total number of carbon atoms of R, and R, is greater than or equal to 20; it being possible for the alkyl radical to be interrupted by an ester group and/or an amido group; or (ii) the radical R 7 denotes a benzyl group and R 6 a C 2 2 alkyl radical; or c) R 4 denotes a C 1 -C 4 alkyl radical; R 5 denotes an (alkyl and/or alkenyl)amidoethyl radical, in which the alkyl and/or alkenyl radical is C13-C21; R, and R 7 form, together with the nitrogen to which they are bonded, a 4,5-dihydroimidazole heterocycle substituted in position 2 by a C 13 -C 21 alkyl and/or alkenyl radical.

2. Dispersion according to claim 1, characterized in that the ratio by weight: ceramide and/or glycoceramide of formula (I)/surface-active agent of formula is less than or equal to 2.

3. Dispersion according to Claim 1 or 2, charac- terized in that in the formula X denotes chlorine or the CH 3 0S0 3 group and R 4 denotes the methyl radical.

4. Dispersion according to any one of Claims 1 to 3, characterized in that the ceramide and/or glycoceramide compounds of formula or their mixtures are chosen from the group formed by: a) the compounds of formula for which R, denotes a saturated or unsaturated alkyl radical derived from a C 16 -C 22 fatty acid; R 2 denotes hydrogen; .J~KL R 3 denotes a saturated linear C 15 hydrocarbon radical; and their mixtures; -1 ~c p~a^ 15 b) the compounds of formula for which R, denotes a saturated or unsaturated alkyl radical derived from a fatty acid; R 2 denotes galactosyl or sulfogalactosyl; and R 3 denotes the group -CH=CH-(CH 2 12 -CH3; and their mixtures. Dispersion according to any one of Claims 1 to 4, characterized in that the cationic surface-active agent, of formula is chosen from the group formed by: a) the tetraalkylammonium halides, such as behenyl- trimethylammonium chloride or dimethyldistearylammonium chloride. b) a quaternary ammonium salt of formula: 0 CH R-C-NH-CH 2 -CH 2 -N \CH 2 CH 3 OSO 3 (III) R in which R denotes a mixture of C 13 -C 21 alkenyl and/or alkyl radicals derived from tallow fatty acids, c) stearamidopropyldimethyl(myristylacetate)ammonium chloride.

6. Dispersion according to any one of Claims 1 to characterized in that the compound of formula is present in concentrations between 0.01 and 15% by weight with respect to the total weight of the dispersion and in that the cationic surface-active agent of formula (II) is present in concentrations between 0.01 and 15% by weight.

7. Cosmetic composition for treating the hair or the skin, characterized in that it contains, in a cosmeti- cally acceptable aqueous vehicle, at least one dispersion defined according to any one of Claims 1 to 6.

8. Composition according to claim 7, characterized in that it contains the ceramide and/or glycoceramide J compound of formula in a concentration between 0.005 16 and 15% by weight and the cationic surface-active agent of formula (II) in concentrations between 0.01 and 15% by weight with respect to the total weight of the composi- tion.

9. Composition according to Claim 7 or 8, charac- terized in that it is provided in the form of more or less thick liquids, of gels, of creams, of aerosol foams or of sprays. Composition according to any one of Claims 7 to 9, characterized in that it additionally contains vis- cosity regulating agents in proportions ranging up to by weight with respect to the total weight of the composition.

11. Composition according to any one of Claims 7 to 10, characterized in that it contains hair or skin conditioning agents chosen from anionic, nonionic or cationic polymers, quaternized or non-quaternized pro- teins or silicones, which do not detrimentally affect the stability of the composition, in proportions between 0.05 and 6% by weight with respect to the total weight of the composition.

12. Composition according to any one of Claims 7 to 11, characterized in that it additionally contains fra- grances, preserving agents, sequestering agents, foam stabilizing agents, propellants, dyes, acidifying or basifying agents or other adjuvants currently used in cosmetics.

13. Use of the composition according to any one of SClaims 7 to 12, as a shampoo or a rinsable hair product, to be applied before or after shampooing, before or after dyeing or bleaching, before or after a permanent wave or hair straightening or between their two stages of reduc- tion and oxidation; as a non-rinsed hair care product, to be applied after a shampoo; as a hair setting or blow drying lotion; or as a skin care product.

14. Process for the cosmetic treatment of the hair or the skin, characterized in that it comprises an appli- cation of a composition according to any one of Claims 7 A Lto 13, optionally followed by rinsing. 0 17 17 54 and 57 This refers to title sheet Title: CATIONIC DISPERSIONS BASED ON CERAMIDES AND/OR GLYCOCERAMIDES Abstract Cationic dispersion containing at least 1) one natural or synthetic ceramide or glycoceramide or a mixture of natural or synthetic ceramides and/or glyco- ceramides of formula where R, denotes C 14 -C 30 alkyl, R 2 denotes hydrogen, (glycosyl)n, (galactosyl)m or sulfo- galactosyl, n having the value 1 to 4 and m having the value 1 to 8, .3 denotes a C15-C26 hydrocarbon radical or a C, 1 -C 26 a-hydroxyalkyl radical in the case of the natural ceramides and/or glycoceramides; 2) a compound of formula (II) where X is an anion and a) R 4 R s and Rg denote C,-C 4 alkyl and R, denotes C 22 alkyl, or b) R 4 and Rs denote C 1 -C 4 alkyl and: R. and R 7 denote C 20 -C 2 2 alkyl; or (ii) R 6 denotes C 22 alkyl and R, denotes benzyl; or c) R 4 denotes Cl-C 4 alkyl, R 5 denotes (alkyl and/or alkenyl)amidoethyl and R 6 and R 7 denote 4,5-dihydroimidazole substituted in position 2 by a C 13 -C 21 alkyl and/or alkenyl. i i; ii INTERNATIONAL SEARCH REPORT International application No. PCT/FR 92/00746 p A. CLASSIFICATION OF SUBJECT MATTER IPC 5 A61K7/06; A61K7/48 According to International Patent Classification (IPC) or to both national classification and IPC B. FIELDS SEARCHED Minimum documentation searched (classification system followed by classification symbols) IPC 5 A61K Documentation searched other than minimum documentation to the extent that such documents are included in the fields searched Electronic data base consulted during the international search (name of data base and, where practicable, search terms used) C. DOCUMENTS CONSIDERED TO BE RELEVANT Category* Citation of document, with indication, where appropriate, of the relevant passages Relevant to claim No. E EP,A,O 446 094 (L'OREAL) 1-3, 11 September 1991 5-10, 12-14 *claims; table 2, examples

25-26; examples 47-49; example 8c* A EP,A,O 278 505 (ESTEE LAUDER INC.) 1-14 17 August 1988 cited in the application *see the whole document* A EP,A,O 260 697 (LION CORPORATION) 1-14 23 March 1988 *claims; page 13, paragraph m; page 14 lines 51-53;* A EP,A,O 420 722 (L'OREAL) 1-14 3 April 1991 *claims; page 4 lines 46-58* O Further documents are listed in the continuation of Box C. See patent family annex. Special categories of cited documents: later document published after the international filing date or priority document defining the general stateof the art which is not considered date and not in conflict with the application but cited to understand to be of particular relevance the principle or theory underlying the invention earlier document but published on or after the international filing date document of particular relevance; the claimed invention cannot be document which may throw doubts on priority claim(s) or which is considered novel or cannot be consiered to involve an inventive cited to establish the publication date of another citation or other step when the document is taken alone special reason (as specified) document of particular relevance; the claimed invention cannot be document referring to an oral disclosure, use, exhibition or other considered to involve an inventive step when the document is means combined with oneor more other such documents,such combination document published prior to the international filing date but later than being obvious to a person skilled in the art the priority date claimed document member of the same patent family Date of the actual completion of the international search Date of mailing of the international search report 22 October 1992 (22.10.92) 20 November 1992 (20.11.92) Name and mailing address of the ISAJ Authorized officer European Patent Office Facsimile No. Telephone No. Form PCT/ISA/210 (second sheet) (July 1992) r i c r ANNEX TO THE INTERNATIONAL SEARCH REPOR ON INTERNATIONAL PATENT APPLICATION No. FR9200746 SA 63236 This annex lists the patent family members relating to the patent documents cited in the above-mentioned international serch report. The members are as contained in the European Patent Office EDP file on The European Patent Office is in no way liable for thes particulars whuich are meey given for the purpose of information. 22/10/9 2 PatntdocnnntPublication Patent family Publication cited in search report date manher(r.) d EP-A-0446094 11-09-91 FR-A- 2658829 30-08-91 EP-A-0278505 17-08-88 DE-A- 3871974 23-07-92 JP-A- 63270617 08-11-88 EP-A-0260697 23-03-88 JP-A- 1025712 27-01-89 JP-A- 63183518 28-07-88 EP-A-0420722 03-04-91 FR-A- 2652002 22-03-91 CA-A- 2025790 22-03-91 JP-A- 3193754 23-08-9 1 ad For more details about this annex we Official journal of the European Patent Office, No. 12/92 can optionally additiolaiLJy contai-n ounuix t iiLv.LL& the effect of improving the cosmetic properties of the RAPPORT DE RECHERCHE INTERNATIONALE Dsmanderoanalso PCT/FR 92/00746 L W.SSEMENT DE L'INVEN11ON (si plusiours sytualft do danuffication soot appllcahl, los idlquer-tos) 7 Solon a& classification Internutional@ des bsrvts (011) on A I& fols sola cl assificain nationhl* ot I& CN CIB 5 A61K7/06; A61K7/48 U. DOMAINES SUR LESQUELS LA RECHERCHE A PORTE Documentation minimal* coonwitbao 4. 4 Li pK~ Documentation consultbo antre quo [a documentation minimal@ dans An mosuro oil do teds documents font purti. des domaines; sur lesquols I& recancho a Pont M. DOCUMENTS CONSIDERES CONINE PERTINENTS1 0 Catkg-rie 0 Identification des documents citks, avec indication, Si n6CeSSakeW No. des revendications dos pas=ne petinentS 13 'iSbes 14 E EP,A,O 446 094 (L'OREAL) 1-3, 11 Septembre 1991 5-10, 12-14 *revendications; tableau 2, exeniples 25-26; exemples 47-49; exeinpie 8c* A EP,A,O 278 505 (ESTEE LAUDER INC.) 1-14 17 Aoi~t 1988 cit6 dans la demande *en entier* A EP,A,O 260 697 (LION CORPORATION) 1-14 23 Mars 1988 *revendications; page 13, paragraphe m; page 14 lignes 51-53; A EP,A,O 420 722 (L'OREAL) 1-14 3 Avril 1991 *revendications; page 4 lignes 46-58* 0 Caldgoules spkclalo do documents iti1 'T document ulthsiur publib postianumsent A An date do d~pat internaionul an A I& date do paloult6 at n'sppaohtnmnt ps W document d~tinlssant rdta gin&l do An technique, A rei do An techniqueo pertinent, mals diApn mrn considifA comma particulldreent petient Iseprincipo on I& thiorio constitumnt Is bas o wentioo Er document antbienr, mai pobli AI& date do dipat ltinflfr- W document particulikenmmt pertinent; Ylnvention rowd- tlodiJ oil aIis Cot. date Ruoe Do pent am o OsidkA commo nanvolleon 1ComiU W' docnment pouvanat jawr on douto sur oo rovendication do lmpllqfsnt -e activii inventiv poloitb ou cit6 pour d~taminer I& data do publication d'une -r document postloaflisment pertinent; rinventlon rover,- ntro citation on pour one raison spidalo (tell@ qu'lndlquis) dlqnuo no Pon am ro osidbs ommo Inpliquant Uao 0( document so rfmt A ono divulgation omit, A on usage, A, activenti tve lorsque Is document an assdAi Ann on na exoton on tans utros moyeas plnslenis unties documents do memo nature, otto ambi- nP document publil avant la, date do dkpat Intanationail, muts nison but &vMdnte powr one potfno do mie. postriuiment A la date do priorlth revendiqube document qui hait patlo deI& mfeo famillo do brevets IV. CMTFICATION Date A Laqneal ia redksarzo Internationale a AtA afecivement achovA. 22 OCTOBRE 1992 Administration chargA del[a rachwrbo Intervationals OICE EUROPEEN DES BREVETS Date apeAditian dn pitset rapport go recterche anfnationale IFISCHER J.P. Fogili PCT/IMAJ21O (iiwo d alja Q(~I M) I I ANNEXE AU RAPPORT DE RECHERCHE INTERNATIONALE RELATIF A LA DEMANDE INTERNATIONALE NO. FR 9200746 SA 63236 La prisente annexe indique les membres do Is Iamilie de brevets relatis mmx documenits brevets citim dam le rapport de recherebe internationale vise ci-deus. Lesdits membres sont contenus au fichier inlormatique do lfice europiee des brevets i In date du Les remseignements fournis sent donnes i titre indicatif et n'engagent pas as responabilite de l'Office europeen des brevets. 22/10/92 Document brevet citi Date de Meinhre(s) de In Date de au rapport do rchereh publication famine de brevet(s) publication EP-A-0446094 11-09-91 FR-A- 2658829 30-08-91 EP-A-0278505 17-08-88 DE-A- 3871974 23-07-92 JP-A- 63270617 08-11-88 EP-A-0260697 23-03-88 JP-A- 1025712 27-01-89 JP-A- 63183518 28-07-88 EP-A-0420722 03-04-91 FR-A- 2652002 22-03-91 CA-A- 2025790 22-03-91 JP-A- 3193754 23-08-91 Pour tout renseagnement concernaut cette awne voir Jounal OfficWe de r~ffic eminopien des br.et, No.12182 I I I I I I r I I 11 1 11 11 I I r I I I I 1 1!