Polyethylene glycol derivatives, their use and cosmetic and pharmaceutical compositions containing them

Abstract

The invention relates to new polyethylene glycol derivatives.These compounds correspond to the general formula: ##STR1## in which R denotes an alkyl and/or alkoxymethyl and/or alkenyloxymethyl radical or a mixture of these radicals, n denotes an average number of units from 20 to 500 and preferably from 30 to 200, and x and y denote average numbers of units from 0 to 8, it being possible for (x+y) to vary from 1 to 8.They can be used in cosmetic or pharmaceutical compositions, in particular as thickeners.

Description

The present invention relates to products derived from polyethylene glycols and from alkylene oxides and/or from alkyl glycidyl ethers or alkenyl glycidyl ethers, their use and cosmetic and/or pharmaceutical compositions in which they are used.

Pharmaceutical and cosmetic compositions intended for use by topical application generally have a high viscosity, being presented in the form of oils, gels, creams or pastes.

This type of presentation is highly valued by the consumer; for the formulator, it most frequently satisfies a practical requirement, namely that of limiting the diffusion of the product, for locally applied compositions, to the treatment zone.

This requirement is particularly important for medicinal compositions, especially if it is desired to carry out local treatments, and it is equally real for the formulation of cosmetic compositions such as compositions intended for hair dyeing, which must not trickle onto the forehead or the neck, and of shampoos in concentrated form, which must not run into the user's eyes, and also for all the other topical applications for which it is desirable to limit the application of the composition to well-defined areas.

A certain number of thickening products have been used in the past for obtaining this result, in particular natural gums and synthetic anionic or cationic polymers.

The use of inorganic salts for increasing the viscosity of solutions of anionic surface-active agents has also been described.

However, it has been found that certain of these products are ineffective for thickening solutions based on surface-active agents, or compositions already containing polymers which flocculate on the addition of ionic thickeners.

Mixtures of polyethylene glycol monoesters and diesters have also been proposed as non-ionic thickeners for cosmetic compositions. However, the proportions of monoesters and diesters are difficult to control; in particular, these products are unstable, which results in a drop in the viscosity of the solutions as a function of time.

A new class of non-ionic compounds which can be used for increasing the viscosity of solutions of ionic or non-ionic surface-active agents has now been discovered, according to the present invention. By virtue of their non-ionic nature, they are more readily compatible with other ionic constituents. Furthermore, they have the great advantage of being chemically stable and of making it possible to obtain viscosities which are substantially constant as a function of time, at ambient temperature or at elevated temperatures.

The products of the invention are solubilised or dispersed in water at concentrations from about 20 to 60%, to give transparent or opaque gels. At lower concentrations, a separation into two phases is generally observed, one phase being gelled and the other completely fluid. However, the introduction of, say, 0.2 to 10% of products of this invention into solutions of surface-active agents makes it possible to obtain limpid or opalescent, homogeneous compositions of substantially increased viscosity.

In certain cases, the products of the invention can be used as foam synergistic agents.

The products can, in certain cases, reduce the aggressiveness of surface-active agents which can be present in certain cosmetic compositions such as soaps, shampoos, eye make-up removal lotions, and foam baths, for example.

The invention thus provides new derivatives of polyethylene glycols and of alkylene oxides and/or of alkyl glycidyl ethers or alkenyl glycidyl ethers, these products essentially being characterised in that they correspond to the general formula (I): ##STR2## in which R denotes an alkyl and/or alkoxymethyl and/or alkenyloxymethyl radical or a mixture of these radicals, n denotes an average number of units from 20 to 500 and preferably from 30 to 200, and x and y denote average numbers of units from 0 to 8 and preferably from 1 to 8, it being possible for the sum (x+y) to vary from 1 to 8, preferably from 2 to 8 and in particular from 2 to 6.

The alkyl radicals are preferably linear radicals having 8 to 18 carbon atoms; the alkoxymethyl or alkenyloxymethyl radicals preferably contain from 8 to 20 carbon atoms in the alkyl or alkenyl part.

The products according to the invention thus essentially consist of a polyoxyethyleneated sequence which is joined, at least at one end and preferably at both ends, to a very limited number of lipophilic units, the proportion by weight of the oxyethyleneated part desirably representing 70 to 95% of the product.

These products can be obtained, in particular, by adding one or more compounds of the general formula: ##STR3## in which R has the same meaning as given above, to mixtures of polyethylene glycols, in the presence of a basic catalyst.

Specific epoxides of the formula (II) which can be used include:

1,2-alkylene oxides such as 1,2-decene oxide, 1,2-dodecene oxide, 1,2-tetradecene oxide, 1,2-hexadecene oxide or 1,2-octadecene oxide; alkyl glycidyl ethers such as decyl glycidyl ether, dodecyl glycidyl ether, tetradecyl glycidyl ether, hexadecyl glycidyl ether, octadecyl glycidyl ether, eicosyl glycidyl ether, 2-methyldodecyl glycidyl ether, 2-methyltetradecyl glycidyl ether, 2-methylpentadecyl glycidyl ether, 2-hexyldecyl glycidyl ether or 2-octyldodecyl glycidyl ether, 2-ethylhexylglycidyl ether; oleyl glycidyl ether, undecylarylglycidyl ether or a mixture of these compounds.

The polyethylene glycols which can be used particularly according to the invention are polyethylene glycols with an average molecular weight of 1,000 to 20,000 and preferably 1,500 to 10,000.

The compounds corresponding to the formula II are preferably used in a molar ratio of 1 to 4:1 and more preferably 1.5 to 3:1 relative to the hydroxyl end groups of the polyethylene glycols.

The basic catalysts which are more particularly preferred in the process for the preparation of the products are alkali metal catalysts such as sodium, potassium, sodium methylate or ethylate or potassium methylate or ethylate, sodium hydroxide or potassium hydroxide.

These catalysts are suitably used in molar proportions of 10 to 300% and preferably 20 to 100%, relative to the polyethylene glycols.

The polyaddition reactions of the compounds of the formula (II) to the polyethylene glycols are generally carried out under an inert atmosphere and preferably under a nitrogen atmosphere, at a temperature of, say, 120.degree. to 180.degree. C.

After neutralisation of the catalyst with hydrochloric acid, if appropriate, the addition products are usually in the form of white or slightly coloured waxes which are soluble or dispersible in water at a concentration of more than 20%, with gelling.

If these products are used at lower concentrations, a separation into two phases is observed, one phase being gelled and containing the products according to the invention, and the other virtually consisting of water. However, it is possible to prepare homogeneous compositions containing the products of the invention at concentrations of, say, 0.2 to 10% and preferably of 1 to 3% by weight, in the presence of one or more surface-active agents chosen from non-ionic, anionic, cationic, amphoteric or zwitterionic surface-active agents, or mixtures thereof, the proportion by weight of the products according to the invention varying from, say, 5 to 40%, relative to the surface-active agents. In this case, the products according to the invention make it possible to obtain limpid or slightly opalescent, aqueous solutions of substantially increased viscosity.

Because of their properties, the products according to the invention can be used as thickeners, in particular in cosmetics and in pharmacy, in the proportions mentioned.

The cosmetic and/or pharmaceutical compositions which form a further aspect of the present invention are essentially characterised in that they contain at least one product corresponding to the formula (I), together with a cosmetically and/or pharmaceutically active ingredient.

In general, the cosmetic and/or pharmaceutical compositions according to the invention are in the form of viscous liquids, gels, dispersions, creams or pastes.

In one embodiment, the cosmetic and/or pharmaceutical compositions according to the invention contain from 0.2 to 10% and preferably from 1 to 3% of the product according to the invention, in the presence of one or more surface-active agents which are non-ionic, anionic, cationic, amphoteric or zwitterionic derivatives, or mixtures thereof, the proportion by weight of the compounds according to the invention preferably being from 5 to 40%, relative to the surface-active agents.

The cosmetic compositions include, in particular, compositions intended for the care of the skin, nails and hair, which can also contain, for example, surface-active products, alkalising or acidifying agents, foam synergistic agents and foam stabilisers, other thickeners, opacifiers, sequestering agents, superfatting agents, antiseptics, preservatives, anionic, cationic, non-ionic or amphoteric polymers, pigments, perfumes, dyestuffs, agents for imparting pearlescence, solvents, sun filters, oxidising agents, reducing agents, electrolytes, oils, waxes, natural substances, protein derivatives, anti-seborrhoea agents, anti-dandruff agents and any other active substance which can have an action in the treatment, care or protection of the skin or hair, and any other adjuvant normally used in cosmetic compositions.

The compositions according to the invention can, in particular, be used as shampoos, foam baths, liquid soaps and lotions or creams to be applied before or after shampooing, before or after dyeing or bleaching or before or after permanent waving.

The compositions can also be used for dyeing or bleaching the hair, as creams or milks for the body or as make-up products. They can contain, in addition to the products of the present invention, other ingredients conventionally used in these types of composition.

The acids and the bases are generally used in amounts so as to adjust the pH of the compositions to 3 to 12 and preferably 3 to 10.

The pharmaceutical compositions also contain active substances intended for the treatment of the human or animal body and pharmaceutically acceptable excipients.

The following Examples further illustrate the present invention.

PREPARATION EXAMPLE (I)

5.8 g of sodium methylate containing 5.64 milliequivalents/g (33 milliequivalents) are added to 150 g (0.075 mol) of polyethylene glycol 2,000 (P.E.G. 2,000) molten at 90.degree. C., under a nitrogen atmosphere, and the mixture is then heated gradually to 150.degree. C., the methanol being removed at ordinary pressure and then under reduced pressure.

54 g (0.225 mol) of 1,2-epoxyhexadecane are then introduced dropwise, at 150.degree.-155.degree. C., in the course of about 40 minutes.

The heating and the stirring are maintained for 1 hour after the addition has ended.

The degree of completion of the reaction, assessed by determining the remaining epoxide groups, is 97.5%.

The basicity introduced is neutralised by adding 33 ml of normal hydrochloric acid.

After drying by heating under reduced pressure, a light yellow wax melting at 29.degree. C. is obtained.

The compound obtained corresponds to the following formula: ##STR4##

The other compounds of the invention, shown in Table 1 which follows, are prepared in the same way; this table indicates the nature of the P.E.G., the nature of the epoxide compound of the formula II together with the amounts used, the molar ratios of the compounds of the formula II to the P.E.G., and the amounts of sodium methylate, expressed in milliequivalents per gram.

TABLE 1__________________________________________________________________________PREPARATION OF THE COMPOUNDS OF THE FORMULA (I) P.E.G. ##STR5## Molar methylateSodiumEx- Molecular Weight Weight ratio (milli-ample weight (g) R (g) II/P.E.G. equivalents)__________________________________________________________________________1 2,000 150 C.sub.14 H.sub.29 54 3 332 3,000 900 C.sub.14 H.sub.29 216 3 1323 3,000 180 C.sub.10 H.sub.21 44 4 284 3,000 150 C.sub.10 H.sub.21 55 6 245 4,000 180 C.sub.14 H.sub.29 32.5 3 206 4,000 200 C.sub.14 H.sub.29 48 4 157 6,000 180 C.sub.10 H.sub.21 22 4 148 6,000 180 C.sub.10 H.sub.21 33 6 149 6,000 180 C.sub.16 H.sub.33 24 3 1410 4,000 200 R.sub.1OCH.sub.2 44.7 3 2211 4,000 100 R.sub.2OCH.sub.2 28 3 2512 10,000 73 R.sub.3OCH.sub.2 10.3 4 1613 3,000 45 R.sub.4OCH.sub.2 10.2 3 6.614 20,000 100 C.sub.14 H.sub.29 9.6 8 2__________________________________________________________________________ R.sub.1 = hexadecyl R.sub.2 = oleyl R.sub.3 = 2ethylhexyl R.sub.4 = CH.sub.2CH(CH.sub.2).sub.9 TABLE II______________________________________CHARACTERISTICS OF THE COMPOUNDS OF THEFORMULA (I) ampleEx- -n ##STR6## R pointMelting______________________________________1 45 3 C.sub.14 H.sub.29 29.degree. C.2 68 3 C.sub.14 H.sub.29 42.degree. C.3 68 4 C.sub.10 H.sub.21 36.degree. C.4 68 6 C.sub.10 H.sub.21 34.degree. C.5 90 3 C.sub.14 H.sub.29 37.degree. C.6 90 4 C.sub.14 H.sub.29 35.degree. C.7 136 4 C.sub.10 H.sub.21 48.degree. C.8 136 6 C.sub.10 H.sub.21 44.degree. C.9 136 3 C.sub.16 H.sub.33 52.degree. C.10 90 3 R.sub.1OCH.sub.2 36.degree. C. R.sub.1 = hexadecyl11 90 3 R.sub.2OCH.sub.2 40.degree. C. R.sub.2 = oleyl12 227 4 R.sub.3OCH.sub.2 53.degree. C. R.sub.3 = 2-ethylhexyl13 68 3 CH.sub.2CH(CH.sub.2).sub.9 OCH.sub.2 42.degree. C.14 454 8 C.sub.14 H.sub.29 55.degree. C.______________________________________

COMPOSITION EXAMPLES

EXAMPLE 1

Shampoo

______________________________________Product of Example 7 3 gCopra bis-(2-hydroxyethyl)-amine oxide containing39% of active ingredient, sold under the nameAROMOX C/12 W by AKZO 5 gSorbitan monolaurate oxyethyleneated with 20 molsof ethylene oxide, sold under the name TWEEN 20by ATLAS 10 gQuaternised cellulose derivative sold underthe name JR. 400 by UNION CARBIDE 0.5 gWater, preservative, perfume, dyestuff q.s.p. 100 g______________________________________ The pH is adjusted to 7 with NaOH.

The viscosity, measured with a Ford cup of diameter 2 mm, is 2 minutes 15 seconds.

This composition is in the form of a thick liquid. It is used as a shampoo. It is found to be unctuous and to adhere well to the hair.

EXAMPLE 2

Shampoo

______________________________________Product of Example 8 2 gC.sub.12 -C.sub.18 --alkyl-dimethylcarboxymethylammoniumhydroxide containing 30% of active ingredient,sold under the name DEHYTON AB 30 by HENKEL 10 gSodium salt of sulphated lauryl alcohol oxy-ethyleneated with 5 mols of ethylene oxide, con-taining 25% of active ingredient, sold under thename SIPON LFS 525 by SINNOVA 10 gPoly-[N--[3-(dimethylammonio)-propyl]-N'--[3-ethylene-oxyethylene-(dimethylammonio)-propyl]-urea] dichloride sold under the name MIRAPOL A 15by MIRANOL 1 gWater, perfume, preservative, dyestuff q.s.p. 100 g______________________________________ The pH is adjusted to 6.5 with NaOH.

The viscosity, measured with a Ford cup of diameter 2 mm, is 58 seconds.

Applied to the hair, the composition is unctuous and adheres well to the hair.

EXAMPLE 3

Shampoo in Gel Form

______________________________________Product of Example 2 5 gSodium salt of sulphated alkanol (C.sub.12 -C.sub.14)oxyethyleneated with 2.2 mols of ethylene oxide(25% of active ingredient) 25 gAdipic acid/dimethylaminohydroxypropyl-diethylene-triamine copolymer sold under the nameCARTARETINE F.4 by SANDOZ 0.8 gWater, perfume, dyestuff, preservative q.s.p. 100 g______________________________________ The pH is adjusted to 8.5 with HCl.

This composition is unctuous and does not run when it is applied to the hair.

EXAMPLE 4

Shampoo in Gel Form

______________________________________Product of Example 8 9 gSodium salt of sulphated alkanol (C.sub.12 -C.sub.14)oxyethyleneated with 2.2 mols of ethylene oxide(25% of active ingredient) 25 gDimethyldiallylammonium chloride/acrylamidecopolymer sold under the name MERQUAT 550 byMERCK 0.3 gWater, perfume, dyestuff, preservative q.s.p. 100 g______________________________________ The pH is adjusted to 5 with NaOH.

As previously, a good adhesion to the hair is found.

EXAMPLE 5

Shampoo in Fluid Gel Form

______________________________________Product of Example 7 5 gSodium salt of sulphated alkanol (C.sub.12 -C.sub.14)oxyethyleneated with 2.2 mols of ethylene oxide,containing 25% of active ingredient 15 gVinylpyrrolidone/dimethylaminoethyl methacrylatecopolymer quaternised by dimethyl sulfate, soldunder the name GAFQUAT 755 by G.A.F. 0.3 gSurface-active agent of the formula:R(OCH.sub.2 CH.sub.2).sub.10 --O--CH.sub.2 --COOH, R being a mixture ofC.sub.12 -C.sub.14 alkyl radicals, sold under the nameAKYPO RLM 100 by CHEM-Y 5 gWater, perfume, preservtive q.s.p. 100 g______________________________________ The pH is adjusted to 6 with NaOH.

The fluid gel is unctuous and perfect to apply to the hair.

EXAMPLE 6

Shampoo

______________________________________Product of Example 7 2 gTriethanolamine alkyl (C.sub.12 -C.sub.14)-sulphate con-taining 40% of active ingredient 25 gWater, perfume, dyestuff, preservative q.s.p. 100 g______________________________________ The pH is adjusted to 7.3 with NaOH.

The shampoo is easy to apply and does not run into the eyes.

EXAMPLE 7

Shampoo

______________________________________Product of Example 7 2 gCycloimidazoline derivative of coconut oil, con-taining 38% of active ingredients, sold under thename MIRANOL C 2M by MIRANOL 10 gWater, perfume, dyestuff, preservative q.s.p. 100 g______________________________________ The pH is adjusted to 8 with HCl.

The shampoo has an unctuous consistency and holds well on the hair.

EXAMPLE 8

Shampoo

______________________________________Product of Example 2 2 gSurface-active agent of the formula:RCHOHCH.sub.2 O(--CH.sub.2 CHOHCH.sub.2 O).sub.n--H, R being amixture of C.sub.9 -C.sub.12 alkyl radicals and n beingequal to 3.5 (statistical value) 10 gWater, perfume, dyestuff, preservative q.s.p. 100 g______________________________________ The pH is adjusted to 7.2 with HCl.

Results similar to those observed in Example 7 are found.

EXAMPLE 9

Rinse in Thick Gel Form

______________________________________Product of Example 2 5 gSorbitan monolaurate oxyethyleneated with 20 molsof ethylene oxide, sold under the name TWEEN 20by ATLAS 5.5 gVinylpyrrolidone/dimethylaminoethyl methacrylatecopolymer quaternised by dimethyl sulphate, soldunder the name GAFQUAT 755 by G.A.F. 0.3 gStearyldimethylbenzylammonium chloride sold underthe name AMMONYX 4002 by FRANCONYX 5 gWater, preservative, perfume, dyestuff q.s.p. 100 g______________________________________ The pH is adjusted to 8 with NaOH.

The composition is unctuous and adheres well to the hair to which it is applied, without running onto the face.

EXAMPLE 10

Thickened Limpid Shampoo

The following composition is prepared:

______________________________________Product of Example 2 1.3 g(Coconut amidopropyl)-dimethylamine oxide contain-ing 30% of active ingredient, sold under the nameAMMONYX CDO by FRANCONYX 30 gSodium salt of sulphated alkanol (C.sub.12 -C.sub.14) oxy-ethyleneated with 2.2 mols of ethylene oxide,containing 25% of active ingredient 20 gWater, preservatives, dyestuffs q.s.p. 100 g______________________________________ pH=7.5 with hydrochloric acid.

The viscosity of this composition at 20.degree. C. is 25,000 cps.

Applied to wet hair, this shampoo gives a copious, firm, stable and mild foam.

The product of this invention serves two purposes here, namely that of a thickener and that of a foam synergistic agent.

EXAMPLE 11

Thickened Liquid Soap

______________________________________Sodium isethionate fatty esters sold under thename FENOPON AC 75 by GAF 10 gProduct of Example 2 2 gWater q.s.p. 100 g______________________________________

EXAMPLE 12

Thickened Liquid Soap

______________________________________Triethanolamine salt of the condensation productof copra fatty acids and protein hydrolysates soldunder the name MAYPON 4 CT by SEPPIC 10 gSorbitan monolaurate oxyethyleneated with 20 molesof ethylene oxide sold under the name TWEEN 20by ATLAS 1 ghexamidine diisethionate 0.05 gProduct of Example 2 2 gWater q.s.p. 100 g______________________________________

In both cases a thickened liquid soap is obtained which is soft to the skin.

EXAMPLE 13

Moisturising Day Cream

______________________________________Sodium stearate 2 gOil of the formula: 30 g ##STR7##prepared according to Example 5 ofFrench Specification No 2 222 351Oil of grape pips 10 gSodium lactate 1 gGlycerine 2 gProduct of Example 4 10 gPreservations qsAntioxidants qsPerfume qsSterile demineralized water q.s.p. 100 g______________________________________

EXAMPLE 14

Colour Base

______________________________________Product of Example 2 10 gMyrj 53 5 gIsopropyl palmitate 15 gLiquid petrolatum 15 gCetiol LC 5 gPigments qsPreservatives qsPerfume qsSterile demineralised water q.s.p. 100 g______________________________________

EXAMPLE 15

Mascara Cream

______________________________________Triethanolamine stearate 10 gCandellilla wax 15 gBeeswax 17 gXanthan gum 0.95 gProduct of Example 4 1 gBlack iron oxide 5 gAminosilicate polysulfide 4 gSoftened water q.s.p. 100 g______________________________________

EXAMPLE 16

Body Milk

______________________________________Product of Example 2 4 gPropylene glycol 4 gTriethanolamine stearate 2 gOil of the formula: 25 g ##STR8##prepared according to Example 5 ofFrench Specification No 2 222 351Soft Almond oil 5 gMethyl parahydroxybenzoate 0.30 gPerfume qsSterile demineralized water q.s.p. 100 g______________________________________

EXAMPLE 17

Nourishing Cream

______________________________________Brij 96 10 gProduct of Example 8 7 gMaize oil 13 gSunflower oil 13 gOil of the formula: 5 g ##STR9##Propylene glycol 3 gPreservatives qsAntioxidants qsPerfume qsSterile demineralized water q.s.p. 100 g______________________________________

EXAMPLE 18

Toilet Cream

______________________________________Glycerol monostearate 5 gTWEEN 20 5 gProduct of Example 2 10 gPropylene glycol 5 gCetiol LC 10 gOil of the formula: 10 g ##STR10##prepared according to Example 5 ofFrench Specifications No 2 222 351Preservatives qsPerfume qsSterile demineralized water q.s.p. 100 g______________________________________

EXAMPLE 19

Hair Lotion

The following lotion is prepared:

______________________________________C.sub.12 -C.sub.18 alkyldimethylcarboxymethyl ammoniumhydroxide containing 30% of acitve ingredient,sold under the name DEHYTHON AB 30 by HENKEL 30 gCationic polymer of the formula ##STR11##which can be prepared as described inFrench Specification No 2 270 846 2 gQuaternary vinylpyrrolidone copolymer having amolecular weight of 100,000 sold under the nameGAFQUAT 734 by General Aniline (50% in ethylalcohol) 1 gProduct of Example 2 2 gTriethanolamine q.s.p.Water q.s.p. 100 g______________________________________

Application is made on sensitised hair after shampooing. It left for five minutes and then rinsed.

EXAMPLE 20

Foam Bath

______________________________________Isopropanolamine lauryl sulphate (45% activeingredient) 15.0 gSodium lauryl ether sulphate with 2 moles ofethylene oxide (25% active ingredient) 45.0 gFatty amine derivatives having a betaine structure(30% active ingredient) 5.0 gProduct of Example 2 2.5 gGlycol distearate 2.0 gPreservative 0.3 gPerfumeWater q.s.p. 100 g______________________________________

EXAMPLE 21

Foam Bath

______________________________________Sodium lauryl ether sulphate with 2 moles ofethylene oxide (25% active ingredient) 60.0 gFatty amine derivatives of betaine structure(30% active ingredient) 2.5 gOleyl sarcosine 1.5 gC.sub.12 -C.sub.18 alkyl aminopropyl dimethyl amineoxide(35% active ingredient) 5.0 gProduct of Example 2 2.5 gGlycol distearate 0.75 gQuaternary vinyl pyrrolidone copolymer of molecularweight 1,000,000 sold under the name GAFQUAT 755 byGAF (20% active ingredient) 2.5 gMethyl parahydroxybenzoate 0.3 gWater q.s.p. 100 g______________________________________

EXAMPLE 22

Aerosol Shaving Foam

The following composition is prepared:

______________________________________Stearine 5.45 gMyristic acid 1.20 gTriethanolamine 3.70 gGlycerine 5.00 gCycloimidazoline derivative of coconut oil(40% active ingredient) sold under the nameMIRANOL C2M Conc by MIRANOL 0.50 gLanolinic acid 0.50 gProduct of Example 2 0.25 gPerfume 0.70 gWater q.s.p. 100 g______________________________________

This composition is made into an aerosol has 96% active ingredient and 4% hydrocarbons as propellant.

EXAMPLE 23

Toilet Soap

______________________________________Pork fat 94.33 gFlakes -Copra oilSoft almond oil 2.00 gProduct of Example 2 1.00 gTitanium dioxide 0.10 gEthylene diamine tetraacetic acid 0.05 gButylhydroxytoluene 0.02 gPerfume 2.50 g______________________________________

EXAMPLE 24

Dermatological Block

______________________________________Fatty acid esters of sodium isethionate, thefatty acids being derived from copra, soldunder the name FENOPON AC 78 by GAF 60.00 gWhite paraffin wax 15.00 gPolyethylene glycol 6000 2.00 gProduct of Example 2 1.00 gQuaternary vinylpyrrolidone copolymer(20% in water) having a molecular weight of 1,000,000sold under the name GAFQUAT 755 byGENERAL ANILINE 3.50 gStearic acid monoethanolamide 10.00 gGlycerine 5.00 gWater 1.30 gTitanium dioxide 0.20 gPerfume 2.00 g______________________________________

EXAMPLE 25

Direct Dye

The following composition is prepared:

______________________________________1-hydroxy-2-amino-4,5-dinitrobenzene 1.00 g1-amino-2-nitro-4-(N methylamino)benzene 0.125 g1-hydroxy-3-nitro-4-aminobenzene 0.03 g1-hydroxy-3-nitro-4-N--.beta.-hydroxyethylaminobenzene 0.45 gCopra diethanolamide 3.00 gLauryl alcohol with 12.5 moles of ethylene oxide 10.00 gProduct of Example 2 2.00 gTriethanolamine q.s.p.Water q.s.p. 100 g______________________________________

This composition is applied to bleached hair. After leaving for 25 minutes, the hair is washed with water. A coppery shade is obtained.

EXAMPLE 26

Oxidation Cream

The following composition is prepared:

______________________________________1-amino-4-(2-methoxyethyl)aminobenzene 1.60 gdihydrochlorideParaaminophenol 0.30 gResorcinol 0.20 gMetaaminophenol 0.25 g1-methyl-2-hydroxy-4-(2-hydroxyethyl)aminobenzene 0.02 g1-(2-hydroxyethyloxy)-2,4-diaminobenzene 0.02 gdihydrochlorideCopra diethanolamide 3.00 gGlycol distearate 1.00 gSodium alkylether sulphate 23.0 gSodium salt of diethylene triaminopentaacetic acid 2.0 gProduct of Example 2 2.0 gAmmonia, 22.degree. B. 10.0 gSodium bisulfite 1 mlWater q.s.p. 100 g______________________________________

40 g of this composition are mixed with 40 g of 20 volume hydrogen peroxide. A thick cream is obtained which is applied to chestnut brown hair. It is left for 30 minutes and then the hair is rinsed. A deep ashen blond shade is obtained.

The commercial products represent the following materials:

______________________________________MYRJ 53 Polyethylene glycol stearate (50 moles of ethylene oxide) sold by ATLASCETIOL LC Cetyl laurate sold by HENKELBRIJ 96 Oleic ether polyoxyethyleneated with 10 moles of ethylene oxide sold by ATLASTWEEN 20 Sorbitan monolaurate oxyethyleneated with 20 moles of ethylene oxide sold by ATLAS.______________________________________

Claims

1. A product having the formula ##STR12## wherein each R represents, independently, alkyl having 8-18 carbon atoms, alkoxymethyl wherein the alkoxy moiety has 8-20 carbon atoms or alkenyloxy methyl wherein the alkenyl moiety has 8-20 carbon atoms, or a mixture thereof, n represents an average number from 20 to 500 and x and y independently represent an average number from 0 to 8 such that the sum (x+y) is from 1 to 8.

2. A product according to claim 1 in which x and y denote an average number of units from 1 to 8 such that (x+y) is from 2 to 8.

3. A product according to claim 1 in which n denotes an average number from 30 to 200.

4. A product according to claim 1 in which the proportion by weight of the oxyethyleneated part represents 70 to 95% of the total product.

5. A product having the formula ##STR13## wherein each R represents independently alkyl having 8 to 18 carbon atoms or a mixture thereof, n represents an average number from 20 to 500 and x and y independently represent an average number from 0 to 8 such that the sum (x+y) is from 1 to 8.

6. The product of claim 5 wherein R is C.sub.14 H.sub.29, n is 68 and x+y is 3.

7. The product of claim 5 wherein R, n and the sum (x+y) are selected from the following combinations:

(a) R is C.sub.14 H.sub.29, n is 45 and x+y is 3,

(b) R is C.sub.14 H.sub.29, n is 68 and x+y is 3,

(c) R is C.sub.10 H.sub.21, n is 68 and x+y is 4,

(d) R is C.sub.10 H.sub.21, n is 68 and x+y is 6,

(e) R is C.sub.14 H.sub.29, n is 90 and x+y is 3,

(f) R is C.sub.14 H.sub.29, n is 90 and x+y is 4,

(g) R is C.sub.10 H.sub.21, n is 136 and x+y is 4,

(h) R is C.sub.10 H.sub.21, n is 136 and x+y is 6,

(i) R is C.sub.16 H.sub.33, n is 136 and x+y is 3, and

(j) R is C.sub.14 H.sub.29, n is 454 and x+y is 8.