Cosmetic product

Details Cosmetic product Cosmetic product

2000-11-02

2003-06-17

Criares, Theodore J. (Department: 1617)

Drug, bio-affecting and body treating compositions

Live hair or scalp treating compositions

Polymer containing

C424S070100, C424S401000, C424S486000, C524S591000, C525S439000, C514S772300

Reexamination Certificate

active

06579517

ABSTRACT:

The present invention relates to a cosmetic composition which comprises at least one crosslinked, water-soluble or water-dispersible polyurethane formed from at least one polyurethane prepolymer having terminal isocyanate groups and from at least one polymer having groups which are reactive toward isocyanate groups (isocyanate-reactive groups).
In cosmetology, polymers with film-forming properties are used for setting, shaping and improving the structure of the hair. These hair treatment compositions generally include a solution of the film former in an alcohol or in a mixture of alcohol and water.
Hairsetting compositions are generally sprayed onto the hair in the form of aqueous-alcoholic solutions. Following the evaporation of the solvent, the individual hairs are held in the desired shape at their points of mutual contact by the polymer which is left behind. The polymers should on the one hand be sufficiently hydrophilic that they can be washed out of the hair, yet on the other hand should be hydrophobic so that the hair treated with the polymers retains its shape even under conditions of high atmospheric humidity and the individual hairs do not stick to one another. In order to obtain a highly efficient hairsetting effect, moreover, it is also desirable to employ polymers which have a relatively high molecular weight and a relatively high glass temperature (at least 15° C.).
A further consideration when formulating hairsetting agents is that because of the environmental regulations governing the emission of volatile organic compounds (VOCs) into the atmosphere it is necessary to reduce the content of alcohol and of propellant.
A further current demand on hair treatment compositions is that they should give the hair a natural appearance and luster even, for example, when the hair concerned is by its very nature particularly vigorous and/or dark.
It is known to employ polysiloxanes, such as polydimethylsiloxane, and polysiloxane derivatives in haircare compositions.
EP-A-017 122 describes the use of polysiloxane-ammonium derivatives in hair washing and hair treatment compositions for improving the combability, softness and body of the hair.
EP-A-729 742 describes hair treatment compositions based on A) an amino-modified silicone terpolymer and B) at least one cationic, silicone-free conditioning agent based on a quaternary ammonium salt.
A disadvantage of the use, described in the two abovementioned publications, of polysiloxanes which are not bonded covalently to the setting polymer is that there are frequent instances of separation of the formulations in the course of storage and following their application to the hair.
EP-A-408 311 describes the use of copolymers comprising units of a) ethylenically unsaturated, hydrophilic monomers and b) ethylenically unsaturated monomers with polysiloxane groups in haircare products.
EP-A-412 704 describes a haircare composition based on a graft copolymer which has monovalent siloxane polymer units on a backbone which is based on a vinyl polymer. After drying, the polymer breaks down into a discontinuous, silicone-containing phase and a continuous, silicone-free phase.
WO 93/03703 describes a hairspray composition comprising: a) from 0.1 to 2% by weight of a surface-active agent, b) from 0.5 to 15% by weight of an ionic resin having an number-average molecular weight of at least 300,000, and c) a liquid vehicle. In this case the ionic resin comprises silicone-containing monomers and, after drying, breaks down into a discontinuous, silicone-containing phase and a silicone-free continuous phase.
EP-A-362 860 describes alcohol-modified silicone ester derivatives and cosmetic compositions comprising them.
None of these publications describes setting polymers based on polyurethanes having a covalent bond of the siloxane groups to the setting polymers via nitrogen-containing groups. In particular, there is no description of crosslinked, water-soluble or water-dispersible polyurethanes which comprise siloxane groups. In addition, the suitability of such polymers for preparing low-VOC formulations is extremely limited.
Owing to their film-forming properties and generally low viscosity in water/ethanol, it is known in cosmetics to employ polyurethanes which are dispersible or soluble in water. For instance, U.S. Pat. No. 4,743,673 describes hydrophilic polyurethane polymers with carboxyl groups in the polymer backbone. These carboxyl groups are generated by hydrolyzing ester groups attached to the polymer backbone by from 30 to 60 minutes of heating with a strong base. This causes hydrolysis not only of the ester groups of the carboxylic ester component but also of those in the polyurethane chain. As a result, the polyurethane chain is cleaved and there is a drastic reduction in the molecular weight of the polyurethanes. Admittedly, there is a mention of the use of the polyurethanes in hairsprays, although in practice the films obtained with these polyurethanes cannot be used for hair cosmetics since they are either insoluble in water or have too low a molecular weight and hence an inadequate setting effect.
DE-A-42 25 045 and WO 94/03515 describe the use of water-soluble or water-dispersible anionic polyurethanes as hairsetting agents. These polyurethanes are synthesized from
a) at least one compound containing two or more active hydrogen atoms per molecule,
b) at least one diol which contains acid groups or salt groups, and
c) at least one diisocyanate.
In terms of their elasticity, hairsetting polymers based on these polyurethanes are in need of improvement and generally lack a pleasant feel in the absence of additives.
DE-A-42 41 118 describes the use of noncrosslinked, cationic polyurethanes and polyureas as auxiliaries in cosmetic and pharmaceutical formulations.
EP-A-619 111 describes the use of polyurethanes based on organic diisocyanates, diols and 2,2-hydroxymethyl-substituted carboxylates of the formula
where A is a hydrogen atom or a C
1
-C
20
-alkyl group in hair fixatives. In this case at least some of the carboxyl groups are neutralized with an organic or inorganic base. Films based on these polyurethanes are soft and tacky, and the hairsetting compositions based thereon, correspondingly, are in need of improvement.
The polyurethanes described in the latter publications can go only part-way toward meeting the requirements made of hairsetting polymers. For instance, with all of the abovementioned polyurethane-based products the desired sleekness of the hair is in need of improvement.
EP-A-636 361 describes a cosmetic composition comprising, in a cosmetically compatible vehicle, at least one pseudolatex based on a polycondensate which comprises at least one polysiloxane unit and at least one polyurethane and/or polyurea unit having anionic or cationic groups. There is no description of crosslinked, water-soluble or water-dispersible polyurethanes. The disclosure content of WO 97/25021 is similar. These cosmetic compositions are suitable, inter alia, for treating keratinous materials. The ease of washout of these film formers, however, is unsatisfactory. In addition, their high siloxane content robs them of the setting effect also required of a hair polymer.
DE-A-195 41 329 and WO 97/17052 describe hair treatment compositions comprising a salt which is dispersible or soluble in water and has the formula I
[A−(X)
n
]
n−
.[H
m
B]
m+
  I
where
A is a cosmetically acceptable aliphatic, cycloaliphatic or aromatic radical, which may have siloxane-containing units and/or fluorine-containing units,
X is a carboxylate, sulfonate, phosphate or phosphonate group;
B is a cosmetically acceptable amine base which may comprise siloxane-containing and/or fluorine-containing units;
n is from 1 to 30; and
m is the valence of the amine B.
Hairspray formulations based on these siloxane-containing salts, on a hairsetting polymer which does not contain siloxane and on a silicone oil lead to films which are easily removed from the surface of the hair by mechanical stress, for example. The setting effect of

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