CH619137A5 - Cosmetic composition containing a crosslinked quaternized polymer - Google Patents

Abstract

The composition contains, in an acceptable cosmetic vehicle, one or more polymers consisting of recurring units of formulae I' and I'' in which: A is an ethylene or propylene group, B1 and B represent a polymethylene group having 3 to 10 carbon atoms, a -CH2-C6H4-CH2- group, a group -(CH2)x-O-(CH2)x -, x being 2 or 3, or a -CH2-CHOH-CH2- group, R1 to R4 represent aliphatic radicals, R5 is a hydrogen atom or an aliphatic, alicyclic, aryl or arylaliphatic radical, X<(-)> and Y<(-)> are halide anions, n and p are integers. These polymers improve the qualities of the hair, in particular the feel and the ease of untangling, when they are applied to the hair before shampooing or before oxidation dyeing. They also have a softening effect on the skin. <IMAGE>

Description

The subject of the invention is a cosmetic composition containing, in a cosmetically acceptable vehicle, at least one polymer of formula I consisting of recurring units of formulas:

r,

R-

x n - a

, e

R,

x

'n - b-

I

R,

not

.n / A

I

R5

. (r)

in which:

A is a polymethylene group having 2 or 3 carbon atoms,

Bt and B, equal or different, represent a group

Rr x

e x

e n - a - n - a - n - b-

I ® | ïe I

R2 L E4

(I ") *

65 polymethylene having 3 to 10 carbon atoms, a xylylidenyl group —CH2 — C6H4 — CH2 - (ortho, meta or para), a group - (CH2) X — O— (CH2) X—, x being a number equal to 2 or 3, or a group - CH2 — CHOH — CH2—,

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619,137

Ri and R3, equal or different, represent an aliphatic radical having 1 to 12 carbon atoms,

R2 and R4, equal or different, represent an aliphatic radical having 1 to 20 carbon atoms,

R5 is a hydrogen atom or an aliphatic, alicyclic, aryl or arylaliphatic radical containing a maximum of 20 carbon atoms,

X® represents a halide anion, in particular chloride or bromide,

Y® is a halide anion, in particular chloride or bromide, n and p are whole numbers.

The polymers consisting of both I and I units are here called polymers of formula I.

It can be seen that, in formula I ", the group Bt is represented with a free valence, which indicates that the units I" are linked by a crosslinking link with analogous units of another macromolecular chain.

In other words, the polymers of formula I have a structure of the following type:

r, x

I1

not:

0

r3 x6

n / A-

Rr

b-

R,

r,

r,

n x

0

-NOT-

.0

• a n — a n -— b-

r,

R.

not

In the polymers of formula I:

Ri and R3 represent in particular an alkyl radical having 1 to 12 carbon atoms;

R2 and R4 represent in particular an alkyl radical having 1 to 20 carbon atoms;

when R5 represents an aliphatic radical, it is in particular an alkyl or cycloalkylalkyl radical having at most 20 carbon atoms, and preferably 1 to 16 carbon atoms; when R5 represents an alicyclic radical, it is in particular a 5 or 6-membered cycloalkyl radical; when R5 represents an arylaliphatic radical, it is in particular an aralkyl radical such as a phenylalkyl radical whose alkyl group preferably contains from 1 to 3 carbon atoms and in particular the benzyl radical.

Preferably Rt = R3 = CH3, in particular with R2 = R4. The terminal groups of the polymers of formula I are of the -Bi-Y or -B-X type.

To prepare the polymers of formula I with Bi = B, a triamine of formula II is subjected to a polycondensation reaction:

Ri-N-A-N-A-N-R3

r2 r5 r4

with an excess of a dihalide of formula III: X-B-X

(or)

in which

Ri, R2, R3, R4, R5, A, B and X are defined as above.

Compound III is used in excess, that is to say that, for 1 mole of triamine II involved, the dihalide III • is reacted in an amount greater than 1 mole.

To prepare the polymers of formula I with Bi different from B, as before, a triamine of formula II is subjected to a polycondensation reaction with an amount substantially

equimolecular of a dihalide of formula III, then the polymer consisting of units of formula I ', obtained intermediate-35 is subjected to the action of a compound of formula Y — Bi - Y, Bi and Y being defined as above .

The compound Y-Bi -Y is made to act either by adding it to the reaction medium, or after having isolated the polymer and having redissolved it in an appropriate solvent.

In the two processes described above, the reaction is carried out for example in a solvent or in a mixture of solvents promoting quaternization reactions, such as water, dimethylformamide, acetonitrile, lower alcohols, especially lower alkanols such as methanol, etc.

The reaction temperature can vary between 10 and 150 ° C, and preferably between 20 and 100 ° C.

The reaction time depends on the nature of the solvent, the starting reagents and the degree of polymerization desired.

The resulting polycondensate is isolated if desired, at the end of the reaction, either by filtration or by concentration of the reaction mixture.

It is possible to adjust the average length of the chains by adding at the start or during the reaction a small amount (1 to 15 mol% relative to reagent II) of a mono-functional reagent such as a tertiary amine.

In this case, at least part of the terminal groups of the polymer I obtained consists of the tertiary amine group used.

The invention extends to cosmetic compositions containing polymers of formula I having such end groups. In the two processes for the preparation of the polymers of formula I mentioned above, the final product is isolated at the end of the reaction either by filtration or by concentration of the reaction mixture and optional crystallization by addition of a suitable anhydrous organic liquid.

To prepare the polymers of formula I (with Bx different from B), the reagent Y-Bi-Y is used in any quantity up to a maximum of 3 moles per 1 mole of starting triamine. Preferably, 0.1 to 3 moles of Y — Bt - Y are used per 1 mole

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4

of triamine. The polymers of formula I are isolated under conditions making it possible to remove the excess of reagent Y-Bt - Y.

It is thus possible to obtain a variety of polymers I having variable degrees of crosslinking and composting a statistical distribution of units of formulas l and I ".

The starting triamines are obtained according to the procedures described in the literature.

For example, the dialkylenetriamines Ni, Ni, N2, N3, N3-pentamethylated are prepared by methylation using formaldehyde and fornic acid of the corresponding dialkylenetriamines.

The triamines of formula are obtained by the same method:

in which:

A = (CH2) 2

ri —— r 2 ~~ r 3 = z r4 — CH3 with rs different from H and CH3.

From triamines in which:

ri = r2 = r4 = r4 = h, themselves obtained according to British Patent No. 913471.

The triamines of formula above are also obtained by this method in which:

ri = r3 = ch3

r2 = R4. = rs # ch3 from the triamines in which:

ri = r3 = H, themselves obtained according to a technique analogous to that described by F.B. Zienty, "J. Of American Chemical Society ”, 68, p. 1388.1945.

The triamines in which:

Ri = R2 = R3 = R4 = R5 7éCH3

are prepared by a method described in US Patent No. 3324182.

Finally, the triamines in which:

ri = r3

r2 = r4

R5 * CH3

are prepared according to S.M. Kupchan, G. Bondesson and A.P. Davies, “J. Of Medicinal Chemistry ”, 15 (1), p. 65.1372.

The polymers of formula I are generally soluble in at least one of the three solvents consisting of water, ethanol or a water / ethanol mixture.

By evaporation of their solution, it is possible to obtain films which in particular have a good affinity with the hair.

As indicated above, the polymers of formula I have advantageous cosmetic properties which make it possible to use them in the preparation of cosmetic compositions. They can also play the role of thickening agents in such compositions.

These cosmetic compositions also comprise at least one vehicle usually used in cosmetic compositions.

The cosmetic compositions of the invention comprise polymers of formula I either as the main active ingredient,

either as an additive.

These cosmetic compositions can be presented in particular in the form of aqueous, alcoholic or hydroalcoholic solutions (the alcohol being in particular a lower alkanol such as ethanol or isopropanol) or in the form of creams, gels, emulsions, or else in the form of aerosol cans also containing a propellant.

Adjuvants are generally present in the compositions

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cosmetics of the invention, for example perfumes, dyes, preservatives, sequestering agents, thickening agents, etc.

It should be noted that the cosmetic compositions according to the invention are both ready-to-use compositions and concentrates which have to be diluted before use. The cosmetic compositions of the invention are therefore not limited to a particular range of concentration of the polymer of formula I.

Generally, in the cosmetic compositions of the invention, the concentration of polymers of formula I is between 0.01 and 10% by weight, in particular between 0.5 and 10% and preferably between 0.5 and 5%.

The polymers of formula I present in particular advantageous cosmetic properties when they are applied to the hair.

Thus when they are applied to the hair either alone or with other active substances, during a treatment such as shampoo, dye, styling, etc., they significantly improve the qualities hair.

For example, they promote treatment and facilitate the disentangling of wet hair. Even in high concentrations, they do not give wet hair a sticky feel

Unlike the usual cationic agents, they do not weigh down dry hair and therefore facilitate swelling hairstyles. They give dry hair qualities of nervousness and a shiny appearance.

They effectively contribute to eliminating the defects of the sensitized hair by treatments such as bleaching, perms or dyes. We know that sensitized hair is often dry, dull and rough, and difficult to untangle and style.

They are in particular of great interest when they are used as pretreatment agents, in particular before an anionic and / or ionic shampoo, or before an oxidation coloring itself followed by an anionic and / or nonionic shampoo.

The hair is then particularly easy to disentangle and has a very soft touch.

They can also be used as pre-treatment agents in other hair treatment operations, for example perming treatments.

The cosmetic compositions according to the invention are in particular cosmetic compositions for hair.

These cosmetic hair compositions generally comprise at least one adjuvant usually used in cosmetic hair compositions.

These cosmetic compositions for hair can be presented in the form of aqueous, alcoholic or hydroalcoholic solutions (the alcohol being a lower alkanol such as ethanol or isopropanol), or in the form of creams, gels or emulsions, or still in the form of sprays. They can also be packaged in the form of aerosol cans, also containing a propellant such as for example nitrogen, nitrous oxide or chlorofluorinated hydrocarbons of the Freon type.

The adjuvants generally present in the cosmetic compositions for hair of the invention are, for example, perfumes, dyes, preserving agents, sequestering agents, thickening agents, emulsifying agents, etc., or alternatively resins usually used in cosmetic compositions for hair.

The polymers of formula I can be present, in the cosmetic compositions for hair according to the invention, either as an additive, or as a main active ingredient, in styling lotions, treating lotions, creams. or styling gels, either as an additive in shampoo, styling, perm, dye, restructuring lotions, antiseborrhoeic treatment lotions, or hair sprays.

The cosmetic compositions for hair according to the invention therefore comprise in particular:

a) Treatment compositions, characterized in that they comprise, as active ingredients, at least one polymer of formula I in aqueous or hydroalcoholic solution.

The content of polymer of formula I can vary between 0.01 and 10% by weight, and preferably between 0.1 and 5%.

The pH of these lotions is close to neutral and can vary, for example, from 6 to 8. We can, if necessary, bring the pH to the desired value by adding either an acid such as citric acid, or a base, in particular an alkanolamine such as monoethanol-amine or triethanolamine.

To treat the hair using such a lotion, the said lotion is applied to wet hair, leaves to act for 3 to 15 minutes, then rinses the hair.

We can then proceed, if desired, to a conventional styling.

b) Shampoos, characterized in that they comprise at least one polymer of formula I and a cationic, nonionic or anionic detergent.

The cationic detergents are in particular long chain quaternary ammoniums, esters of fatty acids and amino alcohols, or polyether amines.

Non-ionic detergents, which can be used in admixture with anionics, include:

- alcohols, diols, alkylphenols, thiols or amides with straight chains from C12 to C18, oxyethylenated, oxypropylenated, glycerolated or glycidolated;

- oxyethylenated and / or oxypropylenated alcohols, thiols or alkylphenols with C2 to C10 chains;

- polycondensates of ethylene oxide and propylene oxide;

- the compounds of formula:

Hyd - (OCH2 - CH—) mOH

CH2

I

SO

I

CH2-CHOH-CH2OH

where m is an integer and Hyd represents a hydrocarbon radical.

Anionic detergents include:

- the alkaline salts, the magnesium salts, the ammonium salts, the amine salts or the amino alcohol salts (in particular ethyanol-amine or isopropanolamine) of the following compounds: fatty acids such as oleic acid, ricinoleic acid, coconut oil acids or hydrogenated coconut oil; alkyl sulfates whose alkyl has a straight chain from C12 to C18; sulfated and ethoxylated alkylamides, with linear chains from Ci2 to Cig; alpha-olefinsulfonates with linear chains from Ci2 to Ci s; carboxylic acids of polyglycolic ethers, of the formula Alk— (OCH2 - CH2) m — OCH2CO2H, Alk being a linear chain from C1 to Ci8 and m an integer;

- condensation products of fatty acids with: sarco-sine and its derivatives, isethionates, polypeptides, alkyl sulfosuccinates or their derivatives, taurine, methyltaurine, etc .;

- sulfosuccinates of ethoxylated Ci2-Cis alcohols, or the corresponding Ci2-Ci8 amide derivatives; and

- alkylbenzenesulfonates, alkylarylpolyethersulfates, monoglyceridesulfates, etc.

All these anionic detergents, as well as many others not mentioned here, are well known and are described in the literature.

These compositions in the form of shampoos can also contain various adjuvants such as, for example, perfumes, dyes, preservatives, thickening agents, foam stabilizing agents, softening agents, or even one or more cosmetic resins.

In these shampoos, the detergent concentration is generated.

generally between 5 and 30% by weight and the concentration of polymer of formula I between 0.01 and 3%, and preferably between 0.3 and 2%.

c) Styling lotions, in particular for sensitized hair, characterized in that they comprise at least one polymer of formula I, in aqueous, alcoholic or hydroalcoholic solution.

They may also contain another cosmetic resin. The cosmetic resins which can be used in such lotions are very varied. These are in particular vinyl or crotonic homopolymers or copolymers, such as for example polyvinylpyrro-lidone, polyvinylpyrrolidone and vinyl acetate copolymers, copolymers of crotonic acid and vinyl acetate, etc.

The concentration of polymers of formula I in these styling lotions generally varies between 0.1 and 5% and, preferably, between 0.2 and 3%, and the concentration of the other cosmetic resin varies substantially between the same proportions.

The pH of these styling lotions generally varies between 3 and 9, preferably between 4.5 and 7.5. The pH can be modified, if desired, for example by adding an alkanolamine such as mono-ethanolamine or triethanolamine.

d) Hair dye compositions, characterized in that they comprise at least one polymer of formula I, a coloring agent and a support.

The support is preferably chosen so as to constitute a cream.

The concentration of polymers of formula I in these dye compositions can vary between 0.1 and 10% by weight, in particular between 0.5 and 10% and, preferably, between 0.5 and 6%.

Of course, in these hair dye compositions, the main active ingredient is the dye (direct dye) or its precursors, and not the polymer of formula I.

It is known that oxidation dyes use so-called oxidation dyes which are aromatic compounds of the diamine, aminophenol or phenol type. These aromatic compounds are transformed into coloring compounds by condensation in the presence of an oxidant, generally hydrogen peroxide. Ortho- or p-diamines or ortho- or p-mono- or di-aminophenols give, by oxidation, strongly coloring compounds. The m-diamines, m-aminophenols and polyphenols give only weak nuances. For this reason, para derivatives are called bases and meta derivatives (and polyphenols) are called modifiers.

The bases mainly used are in particular: p-phenylenediamine, p-toluylenediamine, chloropara-phenylenediamine, p-aminodiphenylamine, o-phenylene-diamine, o-toluylenediamine, 2,5-diaminoanisol, o-aminophenol and p-aminophenol.

The modifiers mainly used are in particular: m-phenylenediamine, m-toluylenediamine, 2,4-diamino-anisol, m-aminophenol, pyrocatechol, resorcinol, hydro-quinone, a-naphthol, 1,5-dihydroxynaphthalene.

Oxidation tinctures mainly contain a mixture of bases and modifiers, with a support allowing presentation in the form of a cream or gelable liquid. They may also contain direct dyes.

In the case of an oxidation dye, the dye composition can be packaged in two parts, the second part being an oxidant such as hydrogen peroxide. The two parts are mixed at the time of use.

Examples of such compositions and their use are given below in the experimental part.

e) Hair lacquers, characterized by the fact that they contain an alcoholic or hydroalcoholic solution of a usual cosmetic resin for lacquers, and at least one polymer of formula I, this solution being placed in an aerosol bottle and mixed with a propellant.

5

5

10

15

20

25

30

35

40

45

50

55

60

65

619,137

One can for example obtain an aerosol lacquer according to the invention by adding the usual cosmetic resin and the polymer of formula I to the mixture of an anhydrous aliphatic alcohol such as ethanol or isopropanol and a propellant or a mixture of liquefied propellants such as halogenated hydrocarbons, of the trichlorofluoromethane or dichlorodifluoromethane type.

In these hair lacquer compositions, the concentration of the cosmetic resin generally varies between 0.5 and 3% by weight, and the concentration of the polymer of formula I generally varies between 0.1 and 3% by weight.

Of course, it is possible to add to these hair lakes according to the invention adjuvants such as dyes, plasticizers or any other usual adjuvant.

f) Restructuring treating lotions, characterized in that they comprise at least one agent having hair restructuring properties and at least one polymer of formula I.

The restructuring agents which can be used in such lotions are, for example, the methylol derivatives described in the French patents of the applicant Nos 1519979,1519980,1519981, 1519982,1527085.

In these lotions, the concentration of the restructuring agent also varies between 0.1 and 10% by weight, and the concentration of the polymer of formula I generally varies between 0.1 and 5% by weight.

g) Pretreatment compositions presented in particular in the form of aqueous or hydroalcoholic solutions optionally in an aerosol bottle, or in the form of creams or gels, these pretreatment compositions being intended to be applied to the hair before shampooing, in particular before an anionic shampoo and / or nonionic, or before an oxidation coloring followed by an anionic and / or nonionic shampoo, or even before a perm treatment.

In these pretreatment compositions, the polymer I constitutes the active ingredient proper, and its concentration generally varies from 0.1 to 10%, and in particular from 0.2 to 5% by weight. The pH of these compositions, close to neutrality, generally varies between 3 and 9, and in particular between 6 and 8.

These pre-treatment compositions can contain various adjuvants (for example resins), usually used in cosmetic compositions for hair, pH modifiers (for example amino alcohols such as monoethanolamine), etc., as indicated for the compositions of paragraph (a) above.

The polymers of formula I also exhibit advantageous cosmetic properties when they are applied to the skin.

In particular, they promote the hydration of the beautiful and therefore prevent its drying out. They also give the skin an appreciable softness to the touch.

The cosmetic compositions according to the invention can be cosmetic compositions for the skin, characterized in that they comprise at least one polymer of formula I.

In addition, they generally comprise at least one adjuvant usually used in cosmetic compositions for the skin.

The cosmetic compositions for the skin according to the invention are presented, for example, in the form of creams, gels, emulsions or aqueous, alcoholic or hydroalcoholic solutions.

The concentration of the polymer of formula I in these skin compositions generally varies between 0.1 and 10% by weight.

The adjuvants generally present in these cosmetic compositions are, for example, perfumes, dyes, preserving agents, thickening agents, sequestering agents, emulsifying agents, etc.

These compositions for the skin constitute in particular treating creams or lotions for the hands or the face, sunscreen creams, tinted creams, milk? make-up removers, foaming liquids for baths, or even deodorant compositions.

These compositions are prepared according to the usual methods.

For example, to obtain a cream, it is possible to emulsify an aqueous phase containing in solution the polymer of formula I and optionally other ingredients or adjuvants, and an oily phase.

The oily phase can consist of various products such as paraffin oil, petroleum jelly oil, sweet almond oil, avocado oil, olive oil, acid esters oily such as glyceryl monostearate, ethyl or isopropyl palmitates, alkyl myristates such as propyl, butyl or cetyl myristates. It is also possible to add fatty alcohols such as cetyl alcohol or waxes such as, for example, beeswax.

The polymers of formula I can be present in the cosmetic compositions for the skin according to the invention either as an additive, or as a main active ingredient in treating creams or lotions for the hands or the face, or even at as an additive in compositions of sunscreen creams, tinted creams, cleansing milks, oils or foaming liquids for baths, etc.

The subject of the present invention is in particular the cosmetic compositions as defined above comprising at least any one of the polymers of formula I described below in the preparation examples. These particular cosmetic compositions are either compositions for hair or compositions for the skin.

The subject of the invention is also the use of a cosmetic composition based on polymer I as defined above for a cosmetic treatment, by application to the hair or to the skin.

In particular, the composition is applied to the hair before an anionic and / or nonionic shampoo, or before an oxidation coloring followed by an anionic and / or nonionic shampoo. The shampoo may itself contain polymers of formula I or other cationic polymers.

The polymers of formula I for which at least one of the substituents Ri, R2, R3, R *, and R5 is different from CH3, that is to say has at least two carbon atoms, are new products. The process for the preparation of these new products is analogous to that described above for the polymers of formula I. The following examples illustrate the invention.

Example 1

Polymer of formula I withBt = B (CH2) 4, Ri = R2 = R3 = R4 = R5 = CH3, A = (CH2) 2 and X = Y = Br.

A mixture of:

- 17.30 g (0.1 mole) of pentamethyldiethylenetriamine,

- 32.4 g (0.15 mole) of 1,4-dibromo-butane in 190 cm3 of methanol. The mixture is concentrated under reduced pressure, the residue is taken up in ethyl ether and the precipitate obtained is filtered off. After drying under vacuum in the presence of phosphoric anhydride, the product obtained contains 40.5% Br; it is soluble in water.

Example 2

Polymer of formula I with B = (CH2) 6, Bi = (CH2) i0, Ri = R2 = R3 = R4 = R5 = CH3, A = (CH2) 3 and X = Y = Br.

A mixture of:

- 20.13 g (0.1 mole) of pentamethyldipropylenetriamine,

- 24.4 g (0.1 mole) of 1,6-dibromo hexane in 200 cm3 of methanol. Then 0.2 mole of 1.10 dibromo-decane (60 g) is added and the heating is continued for 50 h. It is concentrated under reduced pressure, the residue is taken up in ethyl ether and the precipitate obtained is drained. It is dried under reduced pressure in the presence of phosphoric anhydride. It is soluble in a water / ethanol mixture.

By following a procedure analogous to that described in Example I (Examples 3 to 9) or in Example 2 (Examples 10 to 13), the following polymers of formula I were prepared:

6

5

10

15

20

25

30

35

40

45

50

55

60

65

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Ex.

ri r2

r3

r4

AT

r5

B

BI

Dihalide * triamine

X

y

Soluble in

3

ch3

ch3

ch3

ch3

(ch2) 2

ch3

(ch2) 4

(ch2) 4

1.1

Br

Br

Water

4

ch3

ch3

ch3

ch3

(ch2) 2

ch3

(ch2) 4

(ch2) 4

1.2

Br

Br

Water

5

ch3

ch3

ch3

ch3

(ch2) 2

ch3

(ch2) 4

(ch2) 4

1.3

Br

Br

Water

6

ch3

ch3

ch3

ch3

(ch2) 2

ch3

(ch2) 4

(ch2) 4

1.4

Br

Br

Water

7

ch3

ch3

ch3

ch3

(ch2) 3

ch3

(ch2) 6

(ch2) 6

1.5

Br

Br

Water

8

ch3

ch3

ch3

ch3

(ch2) 3

ch3

(ch2) 4

(ch2) 4

1.5

Br

Br

Water

9

ch3

ch3

ch3

ch3

(ch2) 3

ch3

ch2-choh-ch2

ch2-choh-ch2

1.5

Cl

Cl

Water

10

ch3

ch3

ch3

ch3

(ch2) 2

ch3

(CH2) S

(ch2) 2-

0-

- (ch2) 2

1.5

Br

Cl

Water

11

ch3

C4H9

ch3

C4H9

(ch2) 3

C4H9

(ch2) 4

(CH2) IO

1.5

Br

Br

Water / ethanol

12

ch3

c6h13

ch3

C6HI3

(ch2) 3

c6Hi3

(ch2) 2-o- (ch2) 2

(ch2) 6

1.5

Cl

Br

Water / ethanol

13

C4H9

C4H9

C4H9

C4H9

(ch2) 3

C4H9

ch2-choh-ch2

(ch2) 2-

0

- (ch2) 2

1.5

Cl

Br

Water

* Ratio of the number of moles of dihalide (X — B — X + possibly Y — B i — Y) to the number of moles of triamine of formula II

Examples of compositions

Example A:

Coloring shampoo

Polyoxyethylenated nonylphenol (containing 4 moles of ethylene oxide) 25 g

Polyoxyethylenated nonylphenol (containing 9 moles of ethylene oxide) 23

Compound of Example 5 4

96% ethyl alcohol 7

Propylene glycol 14

Ammonia at 22 ° B 10 ml

Dyes

M-diaminoanisol sulfate.

Resorcin

m-Aminophenol base

Nitro p-phenylenediamine ..

p-Toluylenediamine

Trilon B

Sodium bisulphite d = 1.32.

35

Dyes

M-diaminoanisol sulfate.

Resorcin

m-Aminophenol base

p-Aminophenol base

Nitro p-phenylenediamine ..

Trilon B *

Sodium bisulphite d = 1.32.

0.030 g 40

0.400

0.150

0.087

1,000

3,000 45

1,200

Water q.s. 100,000

50 g of this formula are mixed in a bowl with the same amount of hydrogen peroxide at 20 volumes and the gel obtained is applied to the hair with a brush.

Leave to pause for 30 minutes and rinse.

The hair is disentangled easily, the touch is silky. We do the setting and dry.

The hair is shiny, nervous, it has body (volume), the touch is silky and easy to disentangle.

On a brown background, we obtain a chestnut shade.

* Trilon B: Ethylenediamine tetraacetic acid.

Example B:

Cream dye medium (Oxidation coloring)

Cetyl stearyl alcohol 22 g

Oleic diethanolamide 5

Sodium cetylstearyl sulfate 4

Composed of example I 3

Ammonia at 22 ° B 12 ml

0.048 g

0.420

0.150

0.085

0.004

1,000

1,200

Water q.s. 100,000

30 g of this formula are mixed with 45 g of hydrogen peroxide at 20 volumes; a smooth, consistent cream, pleasant to apply and which adheres well to the hair, is obtained.

After a 30 minute break, rinse and dry.

On 100% white hair, we get a blonde.

Detangling wet or dry hair is easy.

Shiny appearance of the hair, pleasant and silky touch.

Example C:

structuring lotion (Application with rinsing)

Mix before use:

2 g of dimethylolethylenethiourea with 25 ml of a solution containing:

Compound of Example 3 5 g

Hydrochloric acid q.s pH 2.5

50 Water q.s.p 100 ml

The mixture is applied to washed and towel-dried hair.

Leave to pause for 10 minutes and rinse.

Detangling is easy, the hair has a soft touch 55 (silky).

We do the styling and dry under helmet.

Dry hair is easily disentangled, it is shiny, nervous and has body (volume).

60 Example D:

styling lotions for sensitized hair 1. An alcoholic solution is prepared with:

Polyvinylpyrrolidone 1.5 g

S5 Compound of Example 9 2.5

Ethyl alcohol q.s 100 ml

Apply on the hair. We do the styling. We dry. The hair is hardened and plasticized.

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They are shiny and have volume; the touch is silky and the disentangling easy.

2. Similar results are obtained by replacing, in the above formula, the polymer of Example 9 with the polymer of Example 13.

3. The lotion of the following formula is prepared:

Polymer of Example 8 1 g

Polyvinylpyrrolidone / vinyl acetate 60:40 1.0 g

Triethanolamine q.s. pH 6

Water q.s.p. 10Ö ml

Apply to bleached hair. We do the setting and dry. •

Results similar to those of the previous example are obtained.

4. The lotion of the following formula is prepared:

Polymer of Example 11 1.1 g

Polyvinylpyrrolidone / vinyl acetate copolymer

60:40 1 g

Ethyl alcohol q.s. 50%

Triethanolamine q.s. pH 7

Water q.s.p 100 ml

Apply to bleached hair. We do the setting and dry.

Results similar to those of the previous example are obtained.

5. The lotion of the following formula is prepared:

Polymer of Example 7 1.3 g

Vinyl acetate / crotonic acid copolymer 90:10 1.7 g Triethanolamine q.s. pH 7.5

Water q.s.p 100 ml

Apply to bleached hair. We do the setting and dry.

Results similar to those of the previous example are obtained.

8. The following solution is prepared:

Polymer of Example 2 1.5 g

Vinyl acetate / crotonic acid copolymer 90:10 1.5 g Monoethanolamine q.s. pH 7

Water q.s.p 100 ml

Apply to bleached hair. We do the setting and dry.

Results similar to those of the previous example are obtained.

Example E:

Treating lotions (Application with rinsing)

1. 30 ml of the following solution are applied to wet and clean hair:

Polymer of Example 4 4 g

Monoethanolamine q.s. pH 7.5

Eauq.s.p 100 ml

Let the lotion act for 5 minutes and rinse.

Hair has a soft feel and is easily detangled.

We do the setting and dry.

Dry hair is easily disentangled.

They are bright, nervous and have body.

2. 25 ml of the following solution is applied to wet and clean hair:

Polymer of Example 3 6 g

Citric acid q.s. pH 6

Water q.s.p 100 ml

Let the lotion act for 5 minutes and rinse.

Hair has a soft feel and is easily detangled.

We do the setting and dry.

Dry hair is easily disentangled.

They are bright, nervous and have body.

Example F:

Shampoos

1. The following solution is prepared:

a-Diol in Cn-C14 condensed with 3 to 4 molecules of glycidol 17 g

Polymer of Example 2 3 g

Lactic acid q.s.p pH 3,5

Water q.s.p 100 cm3

Applied on the head, this clear-looking solution provides abundant and fairly soft lather and promotes the detangling of wet hair. After drying, the hair is nervous, light and shiny.

2. The following solution is prepared:

Ether laurylpolyglycérolé with 4 molecules of glycerol. 15 g

Polymer of Example 5 2 g

Polyoxyethylenated tertiary stearylamine containing 5 moles of ethylene oxide 1.5 g

Lactic acid q.s.p pH 4,5

Water q.s.p 100 cm3

Applied on the head, this clear-looking solution provides an abundant and soft foam that is easily removed on rinsing. The hair is disentangled very easily and, after drying, has bulk and nervousness while remaining soft and docile to styling. 3. The following solution is prepared:

a-Diol in Ch-Cm condensed with 3 to 4 molecules of glycidol 17 g

Polymer of Example 9 3 g

Lactic acid q.s.p pH 3,5

Water q.s.p 100 cm3

Applied on the head, this clear-looking solution provides abundant and fairly soft foam, and improves the disentangling of wet hair. After drying, the hair is soft, shiny and has a light appearance.

Example G:

structuring lotion (Application with rinsing)

1. 2 g of N, N'-di (hydroxymethyl) -ethylenethiourea are mixed before use with 25 cm 3 of a solution containing:

Compound of Example 3 5 g

Hydrochloric acid q.s pH 2.5

Water q.s.p 100 cm3

The mixture is applied to washed and towel-dried hair.

Leave to pause for 10 minutes and rinse.

Detangling is easy, the hair has a soft (silky) feel. We do the styling and dry under helmet.

Dry hair is easily disentangled, it is shiny, nervous and has body (volume).

2. 2 g of N, N'-di (hydroxy-methyl) ethylenethourea are mixed before use with 25 cm 3 of a solution containing:

Compound of example 4 3 g

Hydrochloric acid q.s pH 2.5

Water q.s.p. 100 cm3

The mixture is applied to washed and towel-dried hair.

Leave to pause for 10 minutes and rinse.

Detangling is easy, the hair has a soft feel.

Example H:

Preshampoo compositions

1. 10 g of the following solution are applied to dirty and dry hair:

Compound of example 1 2 g

Monoethanolamine q.s.p pH 7

Water q.s.p 100 cm3

5

10

15

20

25

iO

35

40

45

50

55

60

65

9

619,137

After 2 minutes of pause time, a conventional anionic shampoo is carried out in two stages.

Detangling wet hair is easy, the hair is soft.

After styling and drying, the hair is easily disentangled and has a soft feel.

They are bright and nervous.

This same solution can be packaged as an aerosol.

2. 15 g of the following solution are applied to dirty and dry hair: 10

Compound of example 2 1 g

Compound of example 5 1 g

Monoethanolamine q.s.p pH 7

Water q.s.p 100 cm3 15

After 2 minutes of pause time, a conventional anionic shampoo is carried out in two stages.

Detangling wet hair is easy, the hair is soft. 20

After styling and drying, the hair detangles easily and has a soft feel.

They are bright and nervous.

This same solution can be packaged as an aerosol with nitrogen, or nitrous oxide or Freons as propellants.

Example I:

treatment lotion before coloring 30

20 cm3 of the following solution are applied to dry and dirty hair:

Compound of example 3 3 g

Monoethanolamine q.s.p pH 8 35

Water q.s.p 100 g

After 5 minutes of pause time, a conventional ammoniacal oxidation dye is applied. We leave to pause for 30 minutes.

After rinsing and anionic shampoo, the hair is disentangled very easily.

After styling and drying, the hair is silky, shiny, nervous and easy to comb.

Example J: Anionic shampoo

Triethanolamine lauryl sulfate 10 g

Compound of example 6 1 g

Triethanolamine q.s.p pH 8

Water q.s.p 100 g

Example K:

Composition of pre-shampoo in aerosol foam The following aerosol formula is prepared:

Na cetylstearyl sulfate 1.3 g

Nonylphenol epoxylated to 4 moles of ethylene oxide ... 2.5

Nonylphenol ethoxide with 9 moles of ethylene oxide. 1.5

Compound of Example 3 3.0

Water 81.7

Mixture Freon 114 / Freon 12 (70:30) 10.0

Fill rate 60%.

The foam is applied to dirty and dry hair by rubbing to ensure good distribution of the product.

Then apply a classic anionic shampoo. Leave to pause for 2 to 3 minutes and rinse. Hair has a soft feel and is easily detangled.

After styling and drying, the hair disentangles easily.

Example L:

Treating hand cream

1. The following cream is prepared:

Vaseline oil 10 g

Cetyl alcohol 6

Self-emulsifying glyceryl monostearate 4

Triethanolamine 2

p-Hydroxy methyl benzoate 0.1

Polymer of Example 1 2

Water q.s. 100

This cream is applied to the hands by rubbing to make it penetrate.

The hands are soft and have a pleasant touch.

2. Similar results are obtained by replacing the polymer of Example 1 in the above cream formula with the polymer of Example 13.

R

Claims (7)

619,137 CLAIMS 1. Cosmetic composition characterized in that it contains, in a cosmetically acceptable vehicle, at least one polymer of formula I consisting of recurring units of formulas: r- r. xe n © xe a - n - a - "'n - b r, R, not (T) in which: A is a polymethylene group having 2 or 3 carbon atoms, Bi and B, equal or different, represent a polymethylene group having 3 to 10 carbon atoms, a xylylidenyl group - CH2 - C6H4 — CH2— (ortho, meta or para), a group - (CH2) X — O— (CH2 ) X—, x being a number equal to 2 or 3, or a group —CH2 — CHOH — CH2—, Ri and R3, equal or different, represent an aliphatic radical having 1 to 12 carbon atoms, R2 and R4i, equal or different, represent an aliphatic radical having 1 to 20 carbon atoms, R5 is a hydrogen atom or an aliphatic, ali-cyclic, aryl or arylaliphatic radical containing a maximum of 20 carbon atoms, XS represents a halide anion, Ye is a halide anion, n and p are whole numbers. 2. Composition according to claim 1, characterized in that, in formula I, Xe and Y © represent a chloride or bromide anion. 3. Composition according to claim 1 or 2, characterized in that it contains between 0.5 and 10% by weight of polymer of formula I. 4. Composition according to one of claims 1 to 3, characterized in that it constitutes a dye composition, in particular of oxidation dye. 5. Composition according to one of claims 1 to 3, characterized in that it constitutes a pretreatment composition intended to be applied to the hair before a shampoo, in particular before an anionic and / or nonionic shampoo, 45 (I) or before an oxidation coloring followed by an anionic and / or nonionic shampoo, or before a perm treatment. 6. Use of the composition according to claim 1 for a cosmetic treatment, by applying the composition to the hair or to the skin. 7. Use according to claim 6, characterized in that the composition is applied to the hair, before an anionic and / or nonionic shampoo, or before an oxidation coloring followed by an anionic and / or nonionic shampoo, the shampoo itself being able to contain polymers of formula I or other cationic polymers. Certain polymers having quaternized nitrogen atoms in the macrochain are known and their use has already been proposed as pesticidal agents, as flocculating agents, as surfactants or as ion exchangers. It has now been discovered that, surprisingly, certain crosslinked amino polymers having quaternized ammonium groups exhibit advantageous cosmetic properties when they are introduced into compositions applied to the hair or to the skin, as will be explained below. .