Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Cosmetic – antiperspirant – dentifrice
Reexamination Certificate
1999-02-22
2001-08-21
Page, Thurman K. (Department: 1615)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Cosmetic, antiperspirant, dentifrice
C424S070100, C424S070120, C424S045000
Reexamination Certificate
active
06277386
ABSTRACT:
The present invention relates to a cosmetic composition which comprises at least one water-soluble or water-dispersible polyurethane based on polytetrahydrofurans, polysiloxanes and mixtures thereof and also comprises at least one polyesterdiol.
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 on 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.
DE-A-39 01 325 and DE-A-43 14 305 describe hairsetting compositions comprising as film former copolymers based on A) t-butyl acrylate and/or t-butyl methacrylate, B) acrylic acid and/or methacrylic acid and C) a further free-radically copolymerizable monomer, all or some of the carboxyl groups of the copolymers being in neutralized form. Hairsetting agents based on such copolymers which include carboxyl-containing monomers do indeed generally have satisfactory properties in respect of the setting achieved, the elasticity and the ease of washout from the hair; however, the feel of the styles set with these polymers is perceived as unpleasantly dull and unnatural. An attempt to reduce this effect by adding customary softeners does not in general lead to satisfactory results. Consequently, an improvement in feel is generally achieved at the expense of a reduced setting effect.
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) 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. One disadvantage of the above-mentioned siloxane-containing polymers is the complex synthesis of the constituent monomers. In addition, unreacted macromonomers and nonpolymerizable impurities arising from the preparation, owing to their high molecular weight, are very difficult if not impossible to separate from the siloxane-containing setting polymers. These components, however, are generally not entirely free from toxicological and allergological concerns. In addition, the suitability of such polymers for producing low-VOC formulations is extremely limited. Owing to their film-forming properties and generally low viscosity in water/ethanol, it is known to employ polyesters, polyamides or polyurethanes which are dispersible or soluble in water in cosmetics. For instance, U.S. Pat. No. 4,743,673 describes hydrophilic polyurethane polymers with carboxyl groups in the polymer backbone. These polyurethanes are synthesized from a polyol component, which can be an alkylene glycol, a polyoxyalkylene glycol or a linear polyesterdiol, a carboxylic ester component having hydroxyl or amino groups, and an organic isocyanante or isocyanate precursor. Thus the polyurethane contains, attached to the polymer backbone, ester groups which are subsequently hydrolyzed by from 30 to 60 minutes of refluxing with a strong base such as sodium or potassium hydroxide. The resulting product no longer gives a clear solution either in water or in ethanol. Especially when the polyol component used is a polyesterdiol, treatment with the strong base under reflux conditions 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 polyurethane. 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 describes 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.
They possess a glass temperature of at least 15° C. and an acid number of from 12 to 150. Polyurethanes based on polytetrahydrofurans and/or polysiloxanes are not described. In terms of their elasticity, hairsetting polymers based on these polyurethanes are in need of improvement and generally lack a pleasant feel.
DE-A-42 41 118 describes the use of cationic polyurethanes and polyureas as auxiliaries in cosmetic and pharmaceutical formulations. They are employed in particular as film formers in hairsetting compositions, and are synthesized from
a) at least one diisocyanate which may have already been reacted beforehand with one or more compounds containing two or more active hydrogen atoms per molecule, and
b) at least one diol, primary or secondary amino alcohol, primary or secondary diamine or primary or secondary triamine having one or more tertiary, quaternary or protonated tertiary amine nitrogen atoms.
The polymers have a glass transition temperature of at least 25° C. and an amine numb
Dausch Wilma M
Kim Son Nguyen
Sanner Axel
Schehlmann Volker
BASF - Aktiengesellschaft
Howard S.
Keil & Weinkauf
Page Thurman K.
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