FR2767695A1 - AQUEOUS EMULSION-BASED SKIN CLEANSING AGENTS - Google Patents

Abstract

It is recommended cleansing agents for the skin in the form of emulsions containing:. alkyl- and / or alkenyloligoglycoside-glycerin ethers and. oily bodies. The preparations are particularly gentle on the skin, stable on storage and are suitable in particular as make-up removers for the eyes and sensitive parts of the skin.

Description

Field of the Invention The present invention relates to emulsions

  skin cleansing preparations containing hy-

  drophilised, oily bodies and, where appropriate, fatty alcohols, as well as the use of mixtures as make-up removing agents. State of the art In the field of decorative cosmetics, the most different products are used. A typical makeup composition contains, for example, glycerin monostearate, cetyl alcohol, stearic acid, paraffin oil, cetylstearyl octanoate, octyl palmitate, talc, dioxide titanium, iron oxides, propylene glycol, polysorbates, xanthan,

  magnesium aluminum silicate, glycerin, oils,

  scented, preservatives and water. In black eye pencils or mascaras there are

  waxes, dyes, emulsifiers and thickeners.

  Lipstick sticks also mainly contain, in addition to dyes, waxes and oily bodies, mica,

  titanium dioxide and also, recently,

  applied with silicone. The eye shadows represent habit-

  mixtures of dyes with mica or

  titanium dioxide which may contain as other compounds

  health, talc, paraffin oil, kaolin, sa-

  metallic, wax alcohols and emulsifiers.

  Kajal sticks contain, for example, iron oxides, vegetable oils, waxes, fatty acids, talc and emulsifiers. Cosmetic cleaning agents

  correspondents must therefore remove from the skin as complete

  as many different materials as possible,

  therefore dissolving waxes, oils and silicone compounds ty-

  stings, and simultaneously solubilize pigments such as mica or titanium dioxide. In addition, they should be as soft as possible so that no redness of the skin or irritation of the ocular mucosa appears in the users. Usually preparations of this kind, as described for example in document EP-B1 0705592 (L'Oréal), are presented either in the form of lotions, optionally on wadding supports, or in the form of creams. In this regard, users also want the products, and these are always emulsions, to have sufficient shelf life and not be

  do not irreversibly heat break.

  Consequently, the complex object of the invention consisted in finding new agents for cleaning the skin in the form of an emulsion, having a high cleaning power as well with respect to waxes, oils,

  silicon compounds as pigments that are extraordi-

  generally well compatible with the skin and mucous membranes and

  also have stable storage

particularly high price.

Description of the invention

  The invention relates to skin cleansing agents in emulsion form, containing:

  (a) alkyl- and / or alkenyloligoglycoside ethers-

glycerins, and

(b) oily bodies.

  Surprisingly, it has been found that the agents have a high cleaning power for waxes, oils and pigments, as well as in particular the silicone compounds, that they are extraordinarily well accepted by

  the skin and mucous membranes and that they do not come apart in the heat

  their. The invention includes the discovery that storage stability can be further improved by the addition of fatty alcohols; simultaneously, the consistency of

preparations is increased.

  Alkyl- and / or alkenyloligoglycoside- ethers

glycerins

  The alkyl- and / or alkenyloligoglycoside- ethers

  glycerins represent non-io- hydrophilized glycosides

  known methods which can be obtained according to the corresponding processes of preparative organic chemistry and preferably follow the general formula (I) below,: 1 (R O- [G] p- [Gly] q (1) in which R represents an alkyl or alkenyl radical

  with 1 to 22, preferably 4 to 18 carbon atoms, G represented

  smells like a saccharide radical with 5 or 6 carbon atoms, Gly represents a glycerin radical and p and q independently represent numbers from 1 to 10. For the production of emulsifiers, we start with glycosides

  correspondents which are reacted with a glycide

  rine, a glycerin carbonate or immediately with gly-

  cerine or industrial oligoglycerins. Processes

  correspondents are described in German patent applications

  mands DE-A1 4317472, DE-A1 4335947 and DE-A1 4335956 (Henkel).

  It is also also possible to obtain esters of

  glycerin by common condensation of alkyl glycosides, al-

  fatty cools and glycerin components mentioned above, as stated in document DE-A1 4446446 (Henkel) In this last reaction, mixtures which contain the glycoside-glycerin ethers are immediately obtained

  with fatty alcohols and free glycoside fractions.

  The alkyl- and / or alkenyloligoglycoside component can be derived from aldoses or ketones with 5 to 6 carbon atoms, preferably glucose. The alkyl- and / or ethers

  preferred alkenyloligoglycoside are the alkyl ethers

  and / or alkenyloligoglucoside-glycerins. The index p in the general formula (I) gives the degree of DP oligomerization, that is to say the distribution of the mono- and / or oligoglycosides and represents a number between 1 and 10. While p in the given compound must always be an integer and here especially has the values p = 1 to 6, the value of p is for a

  glycoside-glycerine ether determined a specific size

  born analytically by calculation, which represents the most

  wind a fractional number. Preferably, alkyl- and / or alkenyloligoclycoside glycerol ethers having an average degree of oligomerization p of 1.1 to 3.0 are used. For reasons of application techniques, ethers of alkyl- and / or alkenyloligoglycoside-glycerins are preferred, the degree of which is

  oligomerization is less than 1.7 and is particularly

link between 1.2 and 1.4.

  The alkyl radical or, as the case may be, alkenyl radical R can derive from primary alcohols with 1 to 11, preferably 8 to 10 carbon atoms. As typical examples we can cite

  methanol, butanol, capronic alcohol, capry alcohol-

  lique, capric alcohol and undecyl alcohol as well as

  their industrial mixtures, as obtained, for example,

  ple during the hydrogenation of industrial fatty acid methyl esters or during the hydrogenation of aldehydes in

  Roelen's oxosynthesis. The alkyloligo- ethers are preferred.

  glycoside-glycerin with a chain length of C8 to C10 (DP

  = 1 to 3), which appear as precursors during the separation

  ration by distillation of coconut fatty alcohols in C8 to C18

  industrial and which may present as impurities a

  portion of less than 6% by weight of alcohol in C12 as well as

  alkyloligoglucosides based on C9 to Cll oxoalcohols

  industrial (DP = 1 to 3). The alkyl radical or as the case may be

  alkenyl R can also also be derived from primary alcohols

  res with 12 to 22, preferably 12 to 14 carbon atoms.

  Typical examples include lauric alcohol,

  myristic alcohol, cetyl alcohol, palmol alcohol

  that, stearic alcohol, isostearic alcohol, alcohol

  oleic, elaidic alcohol, petroselinic alcohol, al-

  cool arachic, gadoleic alcohol, behenic alcohol,

  erucic alcohol, brassidic alcohol and their

  industrial swaddles, which can be obtained as it is said

  above. The alkyloligoglycoside ethers are preferred.

  C12 to C14 coconut alcohol glycerin hardened with

DP from 1 to 3.

  Glycerin components may occur

  in the form of monomer and / or oligomer (degree of condensa-

  proper q = 1 to 10). The ethers are preferably obtained

  of glycerol oligomers when instead of glycerin we use

  reads as starting material for industrial oligoglycerins-

  the. We prefer to use products of this type

  when in particular glycerol ethers must be used

  hydrophilic rine with hydrophilic equilibrium values-

  lipophilic (EHL) greater than 15. The bond between the

  health glycerin and the basic glycosidic body is carried out in a completely decisive way via the primary hydroxyl group; in a subordinate manner, however, there may also be an etherification of secondary hydroxyl groups. From the point of view of the application technique, the ethers of

  glycoside-glycerin of formula (I) in which R represents

  has an alkyl radical with 12 to 14 or, as the case may be, 16 to 18 carbon atoms, p represents numbers from 1.1 to 1.6 and q

is worth 1.

Oily body

  As an oily body, for example,

  ple Guerbet alcohols based on fatty alcohols with 6 to 18, preferably 8 to 10 carbon atoms, esters of fatty acids in C6 to C22 linear with fatty alcohols in C6 to C22

  linear, the C6 to C13 carboxylic acid esters branched

  esters, with linear C6 to C22 fatty alcohols, esters

  linear C6 to C22 fatty acids with branched alcohols

  esters, in particular 2-ethylhexanol, esters of linear and / or branched fatty acids with polyvalent alcohols (such as, for example, propylene glycol, the diol dimer or the

  triol trimer) and / or Guerbet alcohols, triglycerides

  based on C6 to C10 fatty acids, mono- / di- mixtures

  / liquid triglycerides based on C6 to C18 fatty acids,

  esters of C6 to C22 fatty alcohols and / or Guer's alcohols

  bet with aromatic carboxylic acids, in particular

  benzoic acid, vegetable oils, primary alcohols

  branched res, substituted cyclohexanes, carbonates

  linear C6 to C22 fatty alcohols, Guer carbonates

  bet, esters of benzoic acid with linear and / or branched C6 to C22 alcohols (for example Finsolv TN), dialkyl ethers, ring opening products

  fatty acids epoxidized with polyols, silicone oils

  cone and / or aliphatic hydrocarbons or according to naphthenic cases. Fatty alcohols Among the fatty alcohols, it is necessary to understand the primary aliphatic alcohols of formula (II)

R OH (II)

  in which R represents an aliphatic hydrocarbon radical

  that, linear or branched with 1 to 22 carbon atoms and with 0 and / or 1, 2, or 3 double bonds. As examples ty-

  we can mention capronic alcohol, capryl alcohol,

  that, 2-ethylhexyl alcohol, capric alcohol, lauric alcohol, isotridecyl alcohol, myristic alcohol, cetyl alcohol, palmoleic alcohol, stearic alcohol, isostearic alcohol, l oleic alcohol, elaidic alcohol,

  petroselin alcohol, linoleic alcohol, linol alcohol

  lenic, eleostearic alcohol, arachic alcohol, gadoleic alcohol, behenic alcohol, erucic alcohol and alcohol

  brassidique as well as their industrial mixtures, which appear

  for example during high pressure hydrogenation

  of industrial methyl esters based on materials

  fatty and oils or aldehydes in Roe's oxosynthesis

  len as well as in the form of monomeric fractions during the

  dimerization of unsaturated fatty alcohols. We prefer the al-

  industrial fatty cools with 12 to 18 carbon atoms, such as coconut, palm, palm kernel or tallow fatty alcohol. In a particularly preferred embodiment of the invention, fatty alcohols are used which have the same

  length of alkyl chain as glycosidyl ethers

  glycerin, so for example cetylstearic alcohol in combination

  born with cetylstearyl glycoside-glycerin ether.

  Makeup Removal Products In a preferred embodiment, the invention further relates to makeup removal products for the eyes and sensitive parts of the skin, containing (a) from 1 to 10, preferably from 2 to 5% by weight. 'alkyl- and / or alkenyloligoglycoside-glycerine ether, (b) from 10 to 80, preferably from 20 to 50% by weight of oily body, as well as (c) from 0 to 20, preferably from 5 to 20% by weight of fatty alcohols, provided that the quantities indicated are supplemented

  % with water and other adjuvants and additives

  tuels. Agents generally have a proportion

  of water from 10 to 90, preferably from 20 to 70% by weight and may

  wind therefore appear as well in the form of emulsions

  fluids than creams. In a particular embodiment

  bind one soaks with preparations, to prepare eye cleaning agents, suitable supports,

  such as cotton wool or viscose, and we market them

read in this form.

  Industrial applicability The preparations according to the invention have excellent compatibility with great cleaning power.

  cosmetic with the skin and are extremely stable to the con-

  servation. The invention also relates to mixtures containing

nant:

  (a) alkyl- and / or alkenyloligoglycoside- ethers

glycerin and (b) oily bodies

as make-up removing products.

  Preparations may contain as others

  adjuvants and additives of mild surfactants, co-

  emulsifiers, superfatting agents, stabilizers, agents giving consistency, thickeners, silicone compounds, biogenic active ingredients, preservatives, hydrotropes, solubilizers,

  scented oils, dyes, or the like.

  As typical examples of suitable mild surfactants, that is to say particularly well accepted by the skin, there may be mentioned the sulfates of alcohol ethers.

  fatty-polyglycol, monoglyceride sulfates, sulfo-

  mono- and / or dialkyl succinates, fatty acid isethionates, fatty acid sarcosinates, acid taurides

  fatty acids, fatty acid glutamates, ether acids

  carboxylic acids, alkyloligoglucosides, glucamides of fatty acids, alkylamidobetaines and / or products of

  condensation of protein fatty acids, the latter of

  wheat protein base. As co-emulsifiers it

  mention should be made, for example, of nonionic surfactants

  genes made up of at least one of the following groups: (1) Adducts of 2 to 3 moles of ethylene oxide

  and / or from 0 to 5 moles of propylene oxide on al-

  linear fatty cools with 8 to 22 carbon atoms, on fatty acids with 12 to 22 carbon atoms and on alkylphenols with 8 to 15 carbon atoms in the alkyl group; (2) C12 to C18 mono- and diesters of products fixing from 1 to 30 moles of ethylene oxide on the glycerin; (3) Mono- and diesters of glycerin and mono- and diesters of sorbitan of saturated and unsaturated fatty acids with 6 to 22 carbon atoms and their fixing products on ethylene oxide; (4) Mono- and oligoglycosides of alkyls with 8 to 22 carbon atoms in the alkyl radical and their ethoxylated analogs; (5) Products for fixing 15 to 60 moles of ethylene oxide on castor oil and / or hardened castor oil; (6) Polyol and in particular polyglycerin esters such as, for example, polyglycerine polyricinoleate or polyglycerine poly-12-hydroxystearate. Mixtures of compounds from several of these classes of substances are also suitable; (7) Fixing products of 12 to 15 moles of ethylene oxide on castor oil and / or hardened castor oil;

  (8) Partial esters based on linear C6 to C22 fatty acids

  res, branched, unsaturated or, where appropriate, saturated, acid

  ricinoleic as well as 12-hydroxystearic acid and gly-

  cerine, polyglycerin, pentaerythritol, dipentaerythri-

  tol, saccharidic alcohols (for example sorbitol),

  alkylglucosides (e.g. methylglucoside, butylglu-

  coside, laurylglucoside) as well as polyglucosides (cellulose); (9) Alkyl triphosphates as well as mono-, di- and / or triPEG-alkyl phosphates; (10) Lanolin alcohols; (11) Polysiloxanepolyalkyl-polyether copolymers or, where appropriate, their corresponding derivatives; (12) Mixed esters of pentaerythritol, fatty acids, citric acid and fatty alcohols according to German patent N 11165574 and / or mixed esters of fatty acids with 6 to 22

  carbon atoms, methylglucose and polyols, preferably

rence glycerin as well as

(13) Polyalkylene glycols.

  Fixing products of ethylene oxide and / or propylene oxide on fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters, as well as sorbitan mono- and diesters of acids fatty or castor oil represent known products that we

  found in trade. These are mixtures of homolo-

  gues whose average degree of alkoxylation corresponds to the ratio of the quantities of ethylene oxide and / or propylene oxide in the substrate, with which the fixing reaction is carried out. C12 to C18 mono- and diesters of ethylene oxide fixing products on glycerin are known

  according to German patent N 2024051 as regreasing agents-

  wise for cosmetic preparations.

  C8 to C18 alkyl mono- and oligoglycosides, their preparation and their manufacture and their use are known from the state of the art. Their manufacture

  takes place in particular by reaction of glucose and oligo-

  saccharides with primary alcohols with 8 to 18 carbon atoms. As regards the glycoside radical, suitable

  both monoglycosides in which a sac radical-

  cyclic carbon is linked by a glycosidic bond to fatty alcohol that the oligomeric glycosides having a degree of oligomerization ranging preferably up to approximately 8. The degree of oligomerization is here a statistical average with the

  base of which is a distribution of counterparts habi-

  tuelle for such industrial products.

  In addition, emulsifiers can be used.

  proud of hermaphrodite surfactants. We design

  as hermaphrodite surfactants the surfactants

  active agents which carry in their molecule at least one am-

  quaternary monium and at least one carboxylate group and one sulfonate group. As hermaphrodite surfactants

  particularly suitable it is necessary to mention what is called

  shovel betaines like N-alkyl-N, N- glycinates

  dimethylamonium, for example alkyl glycinate

  coconut dimethylammonium, N-acylamino glycinates

  propyl-N-dimethylammonium, for example coconut glycinate

  acylaminopropyldimethylammonium and 2-alkyl-3-carboxy-

  methyl-3-hydroxyethylimidazolines each with 8 to 18 carbon atoms in the alkyl group or the acyl group

  as well as coco-acylaminoethylhydroxy glycinate

  ethylcarboxymethyl. we particularly prefer the derivative

  fatty acid amide known as CTFA cocami-

  dopropyl-betaine. As particularly suitable emulsifiers

  requested, mention may be made of ampholytic surfactants.

  Among the ampholytic surfactants include:

  surfactant compounds which contain in their molecule, or-

  be a C8 to C18 alkyl or acyl group, at least one free amino group and at least one -COOH or -SO3H group and which are capable of forming internal salts. As examples of agents

  suitable ampholytic surfactants include N-

  alkylglycines, N-alkylpropionic acids, N- acids

  alkylaminobutyric, N-alkyliminodipropionic acids,

  N-hydroxyethyl-N-alkylamidopropylglycines, N-

  alkyltaurines, N-alkylsarcosines, 2-alkyla- acids

  minopropionics and alkylaminoacetic acids having cha-

  cun of about 8 to 18 carbon atoms in the alkyl group.

  As particularly suitable ampholytic surfactants

  properties include N-coco alkylaminopropionate, coco-acylaminoethyl aminopropionate and C12 to C18carcosine acyl. In addition to the ampholytic emulsifiers, quaternary emulsifiers must also be mentioned, among which those of the Esterquat type are preferred, preferably the

  salts of triethanolamine esters of methyl di-fatty acids

  quaternized. As super-fattening agents, substances such as lanolin and lecithin must be mentioned

  as well as lanolin and polyethoxy lecithin derivatives

  les and / or acylated, fatty acid esters of polyols,

  monoglycerides and alkanolamides of fatty acids, the latter

  also serve simultaneously as foam stabilizers. As agents giving consistency,

  first mention fatty alcohols with 12 to 22 ato-

  carbon and preferably with 12 to 18 carbon atoms and partial glycerides. We prefer a combination

  of these materials with alkyloligoglucosides and / or N-

  fatty acid methylglucamides with the same chain length and / or polyglycerin poly12-hydroxystearates. The

  suitable thickening agents are for example polysac-

  charides, in particular xanthan gum, guar-guar,

  agar-agar, alginates and tyloses, carboxym-

  thylcellulose and hydroxymethylcellulose, or the mo-

  polyethylene glycol no- and diesters of fatty acids, polyacrylates (for example Carbopol from Goodrich or

  Synthalene from Sigma), polyacrylamides, polyvinyl alcohol

  nyl and polyvinylpyrrolidone, surfactants such as, for example, glycerides of ethoxylated fatty acids, esters of fatty acids with polyols, such as pentaerythritol or trimethylolpropane, fatty alcohol ethoxylates with concentrated homologous distribution or alkyloligoglucosides as well as electrolytes like salt

  and ammonium chloride.

  Suitable silicone compounds are by

  example dimethylpolysiloxanes, methylphenylpoly-

  siloxanes, cyclic silicones as well as amino-modified silicone compounds, fatty acid, alcohol, polyether, epoxy, fluorine, glycoside and / or alkyl, which at room temperature can be present in both liquid and resin form . As typical examples of fats, glycerides may be mentioned, as waxes, beeswax, carnauba wax, candelilla wax, montan wax, paraffin wax should also be mentioned.

  or the micro-waxes, possibly in combination with

  hydrophilic res, for example cetylstearyl alcohol or partial glycerides. As stabilizers it is necessary to mention

  metal salts of fatty acids such as, for example, stearate

  magnesium, aluminum and / or zinc spleen. Among the ma-

  biogenic active ingredients, for example, the

  copherol, tocopherol acetate, tocopherate palmitate

  rol, ascorbic acid, deoxyribonucleic acid,

  retinol, bisabolol, allantoin, phytanetriol, pan-

  thenol, AHA acids, amino acids, ceramides,

  pseudo-ceramides, essential oils, vegetable extracts

  vitamin levels and complexes. As bulking agents

  ment for aqueous phases it is necessary to mention montmorillonite, ores of clay type, pemulene as well as carbopol types with alkyl modification (Goodrich). To improve the flow behavior, hydrotropes such as ethanol, isopropyl alcohol or polyols can also be used. The polyols envisaged here preferably have from 2 to 15 carbon atoms and at least two hydroxyl groups. As typical examples, the following may be mentioned: * glycerin; * alkylene glycols such as, for example, ethylene glycol,

* diethylene glycol, propylene glycol, butylene gly-

  col, hexylene glycol as well as polyethylene glycols having an average molecular weight of 100 to 1000 daltons; * industrial mixtures of oligoglycerins with a specific degree of condensation of 1.5 to 10 such as for example

  industrial diglycerin mixtures with a di-

glycerin from 40 to 50% by weight;

  * methylol compounds, such as, for example, trimethylo-

  lethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol; * lower alkyl-glucosides, in particular those which have from 1 to 8 carbon atoms in the alkyl radical such as for example methyl- and butyglucoside;

  * saccharide alcohols having 5 to 12 carbon atoms

  bone such as, for example, sorbitol or mannitol, * saccharides with 5 to 12 carbon atoms such as, for example, glucose or sucrose;

  * aminosaccharides such as, for example, glucamine.

  As preservatives, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid can be used, for example. As perfume oils we will mention extracts of flowers (lavender, rose, jasmine, neroli), stems and leaves (geranium, pat-

  chouli, petit-grain), fruit (anise, coriander, cumin, ge-

  nièvre), fruit peel (bergamot, lemon, orange), roots (mace, angelica, celery, cardamom, costus, iris, calmus), wood (sandalwood, guaiacol, cedar, rose) , herbs and grasses (tarragon, lemon grass, sage, thyme), needles and twigs (spruce, fir, pine, pine

  mountain), resins and balms (galbanum, elemi, ben-

  join, myrrh, frankincense, opoponax). In addition, raw materials of animal origin, such as

  musk, civet and castoreum. As syn-

  thetic or semi-synthetic, we must mention the am-

  broxane, eugenol, isoeugenol, citronellal, hydro-

  citronellal, geraniol, citronellol, gerate acetate

  nyle, citral, ionone and methylionone.

  As coloring agents, suitable substances which are accepted for cosmetic purposes, such as those collected for example in the publication "Kosmetische Fârbmittel" (cosmetic agents) of the Farbstoffkommission der Deutschen Forschungsgemeinschaft (comission of colorants from the German research society), ed. . Chemie, Weinheim, 1984, pp. 81-106. These dyes are usually used in concentrations of 0.001 to 0.1% by weight relative to

the whole mixture.

  The total proportion of adjuvants and additives

  may amount to 1 to 50, preferably 5 to 40% by weight -

  compared to agents. The manufacturing of agents can be

  perform by cold or hot processes; preferably, one works according to the phase inversion temperature process. Examples The quantitative data in the examples of

  compositions below must be understood in percenta-

  weight ages (with the addition of water in qs 100% by weight).

  Cleansing cream Glyceryl cetearylglucosides, 0

  Glyceryl stearate (and) ceta-

  reth-12/20 (and) cetearyl alcohol (and) pal- 3.0 cetyl mitate Almond oil 0.0 Decyl oleate 3.0 Cetaryl isononanoate 3.0 Glycerin (86% by weight) _ 3, 0 Cleansing cream Glyceryl cetearylglucosides, 0 Polyglyceryl 3-diisostearate 4.0 Glyceryl oleate 2.0 Beeswax 3.0 Dicaprylic ether, 0 Octyldodecanol 8.0 Coconut caprylate caprate _ 5.0 Glycerin (86% by weight), 0 Magnesium sulfate 1.0 Skin cleansing emulsion Coconut glyceryl glycosides, 0

  Glyceryl stearate (and) ceta-

  reth-12/20 (and) cetearyl alcohol (and) pal- 5.0 cetyl mitate Wheat protein hydrolyzed with coconut potassium fatty acid 2.0 Almond oil 0.0 2-Ethylhexyl palmitate 3, 0 Cetaryl isononanoate 3.0 Propylene glycol 3.0 Eye cleansing emulsion Glyceryl cetearylglucosides, 0

  Cetarylglucosides (and) alcohol

  tearyl 3.0 Rose oil 3.0 Almond oil 2.0 Vaseline 8.0 Polyacrylamide (and) isoparaffin C13 to C14 and laureth-7 0.3 Glycerin (86% by weight) 3.0

Claims (10)

R E V E N D I C A T IONS   1) Skin cleansing agents in the form of a comfortable emulsion   containing * ethers of alkyl- and / or alkenyloligoglycosides-glycerins and * oily bodies.   2) Agents according to claim 1, characterized in that   they contain alkyl- and / or alkenyloligoglyco- ethers   sides of formula (I) R O [G] p- [Gly] q (I) in which R represents an alkyl or alkenyl radical   with 1 to 22 carbon atoms, G represents a sac radical-   charidic with 5 to 6 carbon atoms, Gly represents a glycerin radical and p and q independently represent one   on the other numbers ranging from 1 to 10.   3) Agents according to Claims 1 and 2,   characterized in that they contain glycoside-glycerin ethers of formula i (I) in which R represents an alkyl radical with 12 to 14 carbon atoms, p represents a number from 1.1 to 1.6 and q is 1.   4) Agents according to claims 1 and 2,   characterized in that they contain glycoside-glycerin ethers of formula (I) in which R represents an alkyl radical with 16 to 18 carbon atoms, p represents a number from 1.1 to 1.6 and q is 1.   5) Agents according to Claims 1 to 4,   characterized in that they contain oily bodies which are chosen from the group formed by Guerbet alcohols based on fatty alcohols   with 6 to 18 carbon atoms, preferably with 8 to 10 ato-   carbon, esters of linear C6 to C20 fatty acids with linear C6 to C20 fatty alcohols, esters of C6 to C13 carboxylic acids branched with linear C6 to C20 fatty alcohols, esters linear C6 to C18 fatty acids with branched alcohols, linear and / or branched fatty acid esters with polyvalent alcohols   and / or Guerbet alcohols, acid-based triglycerides   C6 to ClO fats, C6 to C22 fatty alcohol esters and / or Guerbet alcohols with carboxylic acids   vegetable essences, branched primary alcohols, cyclo-   substituted hexanes, Guerbet carbonates, dialkyl ethers, ring opening products of fatty acid esters epoxidized with polyols, silicone oils and / or   aliphatic hydrocarbons or, depending on the naphthenic case.   6) Agents according to claims 1 to 5,   characterized in that they additionally contain fatty alcohols of formula (II) R OH (II)   in which R represents an aliphatic hydrocarbon radical   that, linear or branched with 6 to 22 carbon atoms and with   0 and / or 1, 2, or 3 double bonds.   7) Agents according to claim 6, characterized in that   they contain fatty alcohols which have the same lon-   alkyl chain alcohol than glycosidyl ethers glycerin.   8) Agents according to claims 1 to 7,   characterized in that they contain   * from 1 to 10% by weight of alkyl- and / or alkenylol ethers   goglycoside-glycerine, * from 10 to 80% by weight of oily body, * from 0 to 20% by weight of fatty alcohols, * provided that the quantities indicated are supplemented at   % by weight with water and other adjuvants and additives usual tifs.   9) Agents according to claims 1 to 8, characterized in that   they have a proportion of water of 10 to 90% by weight.   10) Use of mixtures containing * alkyl- and / or alkenyloligoglycoside-glycerol ethers and * oily bodies as make-up removing products.