Use of polymers containing polysiloxane for cosmetic...

Drug – bio-affecting and body treating compositions – Live hair or scalp treating compositions – Polymer containing

Reexamination Certificate

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C424S070100, C424S070110, C424S047000, C510S119000

Reexamination Certificate

active

06403074

ABSTRACT:

This application is a 371 of PCT/EP98/04482, filed Jul. 20, 1998.
Synthetic polymers have been employed successfully for the setting of hair styles for almost 50 years. Whereas to start with vinyl lactam homopolymers and copolymers were preferably employed, polymers containing carboxylate groups gained in importance later on. The desired profile of properties, such as firm setting at high atmospheric humidity, elasticity, ease of wash-off from the hair, and compatibility with the other formulation components, is achieved by copolymerizing a combination of hydrophobic, elasticizing and carboxyl-containing monomers.
Although these requirements are nowadays met by a variety of polymer types, more and more frequently the feel of the hairstyles set with these polymers is perceived as being unpleasantly dull and unnatural. Attempts to improve formulations by means of additives have not to date led to entirely satisfactory results: the addition of customary plasticizers, although improving the feel, at the same time reduces the setting effect in many cases. The polysiloxanes frequently employed are incompatible with the polar polymers and often require further additives to allow them to be formulated at all. Separation can lead to problems both during storage of the formulation and during its use.
There has therefore been no lack of attempts to bind polysiloxane groups covalently to the hairsetting polymer in order to prevent separation. For example, European Patent Application EP 0 408 311 describes haircare polymers formed from a monomer which contains polysiloxane groups and from customary hydrophilic and hydrophobic monomers. European Patent Applications EP 0 412 704 to EP 0 412 707 propose polymerizing polysiloxane groups, in the form of macromonomers with molar masses from 1000 to 50,000, with customary hydrophobic and hydrophilic monomers. The synthesis of these monomers is extremely laborious. It is difficult to separate unreacted macromonomers and their unreactive impurities from the polymers, owing to their high molecular weight. They constitute a toxicological and allergenic risk. Moreover, the resulting copolymers can often only achieve a good effect by being formulated in combination with further polymers, carriers and other auxiliaries, as detailed in the abovementioned specifications.
DE 42 40 108 describes polysiloxane-containing binders suitable as dirt-repelling coatings, especially as antigraffiti coatings. However, these binders are paintlike and are not suitable for cosmetic purposes.
DE 16 45 569 describes a process for preparing organosilicone graft copolymers and their use as foam compositions.
It is an object of the present invention to provide polymers for hair cosmetology which do not have the disadvantages set out above.
We have found that this object is achieved by the use of polymers which are water-soluble or water-dispersible or which, if consisting of monomers with neutralizable radicals, are soluble in water or dispersible in water in neutralized form, which are obtainable by subjecting
(a) ethylenically unsaturated monomers to free-radical polymerization in the presence of
(b) polyalkylene oxide-containing silicone derivatives,
for cosmetic formulations.
By “water-dispersible” in the context of the invention are meant polymers which in contact with water within 24 hours form a fluid in which no solid particles can be made out with the naked eye. To test whether a polymer is water-dispersible, 100 mg of the polymer in the form of a film 100 &mgr;m thick are placed in 100 ml of water (20° C.) and shaken on a commercially customary shaking table for 24 hours. If solid particles can no longer be perceived after the shaking, but the fluid possesses turbidity, the polymer is water-dispersible; in the absence of turbidity, it is referred to as water-soluble.
If the silicone compounds are not present during polymerization but instead are mixed in after polymerization, then the result is usually very soft, tacky films unsuitable for the applications in hair cosmetology in accordance with the invention (see Comparative Examples 8 and 24).
This is evident by the fact that grafting of the polymers onto the silicone compounds may possibly occur during polymerization, and that this contributes to the good film properties such as freedom from tack, high surface smoothness, and hardness.
However, it is also possible to conceive mechanisms other than grafting by which the novel polymers arrive at their advantageous properties.
As suitable polymerizable monomers (a) it is possible to use, preferably, ethylenically unsaturated monomers. In this context use can be made of either a single monomer or of combinations of two or more monomers. By polymerizable is meant that the monomers used can be polymerized using any conventional synthetic method.
Such a method can, for example, be solution, emulsion, inverse emulsion, suspension, inverse suspension or precipitation polymerization, without the methods which can be used being restricted to these. In the case of solution polymerization, the solvent used can be water, customary organic solvents, or the novel silicone derivatives themselves.
Monomers which can be polymerized in a reaction which is initiated by free radicals are preferred. The term ethylenically unsaturated means that the monomers possess at least one polymerizable carbon-carbon double bond, which may be in mono-, di-, tri- or tetra-substituted form.
The monomers (a) of the polysiloxane-comprising polymers of the present invention can account for from 50 to 99.9% by weight, preferably from 70 to 99% by weight and, with particular preference, from 85 to 98% by weight.
The preferred ethylenically unsaturated monomers (a) can be described by the following formula:
X—C(O)CR
7
═CHR
6
where
X is selected from the group consisting of —OH, —OM, —OR
8
, NH
2
, —NHR
8
, N(R
8
)
2
;
M is a cation selected from the group consisting of: Na
+
, K
+
, Mg
++
, Ca
++
, Zn
++
, NH
4
+
, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium;
the radicals R
8
can be identical or different and can be selected from the group consisting of —H, C1-C40 linear- or branched-chain alkyls, N,N-dimethylaminoethyl, 2-hydroxyethyl, 2-methoxyethyl, 2-ethoxyethyl, hydroxypropyl, methoxypropyl and ethoxypropyl;
R
7
and R
6
are selected independently of one another from the group consisting of: —H, C
1
-C
8
linear- or branched-chain alkyls, methoxy, ethoxy, 2-hydroxyethoxy, 2-methoxyethoxy and 2-ethoxyethyl.
Representative, but nonlimiting, examples of suitable monomers (a) are acrylic acid and its salts, esters and amides. The salts can be derived from any desired nontoxic metal, ammonium or substituted ammonium counterions.
The esters can be derived from C
1
-C
40
linear, C
3
-C
40
branched-chain or C
3
-C
40
carbocyclic alcohols, from polyfunctional alcohols having 2 to about 8 hydroxyls, such as ethylene glycol, hexylene glycol, glycerol and 1,2,6-hexanetriol, from amino alcohols or from alcohol ethers, such as methoxyethanol and ethoxyethanol or polyethylene glycols.
Also suitable are N,N-dialkylaminoalkyl acrylates and methacrylates and N-dialkylaminoalkylacryl- and -methacrylamides of the formula (II)
where R
9
=H, alkyl of 1 to 8 carbons,
R
10
=H, methyl,
R
11
=alkylene of 1 to 24 carbons, optionally substituted by alkyl,
R
12
, R
13
=C
1
-C
40
alkyl,
Z=nitrogen if x=1 or oxygen if x=0.
The amides can be unsubstituted, N-alkyl- or N-alkylamino-monosubstituted or N,N-dialkyl-substituted or N,N-dialkylamino-disubstituted, the alkyls or alkylaminos being derived from C1-C40 linear, C3-C40 branched-chain or C3-C40 carbocyclic units. In addition, the alkylaminos can be quaternized.
Preferred monomers of the formula II are N,N-dimethylaminomethyl, N,N-diethylaminomethyl, N,N-dimethylaminoethyl and N,N-diethylaminoethyl (meth)acrylates.
Monomers (a) which can likewise be used are substituted acrylic acids and salts, esters and amides thereof, the substituents in the ca

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