Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From silicon reactant having at least one...
Reexamination Certificate
1998-04-29
2002-04-02
Sergent, Rabon (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From silicon reactant having at least one...
C424S070100, C424S070110, C424S070120, C424S070122, C424S070170, C424S078080, C424S078370, C524S591000, C524S840000, C528S049000, C528S059000, C528S060000, C528S061000, C528S071000, C528S080000, C528S083000
Reexamination Certificate
active
06365697
ABSTRACT:
The present present invention relates to water-soluble or water-dispersible polyurethanes with terminal acid groups, to their preparation and to their use in cosmetology.
Water-soluble or water-dispersible polymers, for example polyesters, polyamides or polyurethanes, are becoming increasingly important on the basis of their particularly low viscosity in water/ethanol. For instance, water-soluble polyurethanes comprising carboxyl-containing diols in copolymerized form are disclosed in U.S. Pat. Nos. 3,412,054 and 3,658,939. They are used as adhesives, as coating compositions and in printing inks. Water-dispersible polyurethanes containing sulfonate groups and/or carboxylate groups are disclosed in DE-A-15 70 615. They are used, for example, for coating and for the impregnation of textiles, leather, paper, wood and metals. Patent documents U.S. Pat. No. 4,300,580, U.S. Pat. No. 3,734,874, DE-A-26 33 418 and WO-A-89/07118 disclose polyesters which contain NaSO
3
groups and whose main chain is synthesized by condensation reaction and can be broken into shorter segments by hydrolyzing the ester groups.
It is also known that maleic anhydride and trimellitic anhydride can be used to prepare water-soluble esters. The anhydride group provides carboxyl groups which, by neutralization with amines, metal hydroxides and metal carbonates, are converted to water-solubilizing carboxylate groups. DE-A-26 37 167 and U.S. Pat. No. 3,523,998 disclose that polycarboxylic acids and their anhydrides can, as polymer components, also contribute to rendering polyesters soluble in water. DE-A-21 44 878 describes polyurethanes which are reaction products of digested casein, water-dispersible polyurethanes and formaldehyde. The polyurethane component employed is, inter alia, a latex obtainable by reacting a polyurethane prepolymer with a sodium taurine solution. The latex has a relatively low molecular weight and a low content of ionogenic or ionic groups, since other than the sulfonate groups from the taurine it contains no further ionogenic or ionic groups. A film obtained from the latex, therefore, is insoluble in water without dispersants. The resulting latex is then reacted with casein and formaldehyde to give the abovementioned reaction product. However, no cosmetic application of such polymers has yet been described.
Film-forming polymers are used in cosmetology to improve the structure of and to shape and set the hair. The hair treatment compositions generally comprise a solution of the film former in an alcohol or in a mixture of alcohol and water.
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, from a carboxylic ester component containing hydroxyl or amino groups, and from an organic isocyanate or isocyanate precursor. The polyurethane therefore contains ester groups attached to the polymer backbone, which are subsequently hydrolyzed by heating under reflux for 30-60 minutes with a strong base, such as sodium hydroxide or potassium hydroxide. The product no longer gives a clear solution either in water or in ethanol. Especially when using a polyesterdiol as polyol component, treatment with the strong base under reflux conditions gives rise to hydrolysis not only of the ester groups of the carboxylic ester component but also of those present in the polyurethane chain. The latter is thus cleaved, with a drastic reduction in the molecular weight of the polyurethanes. Admittedly, use of polyurethanes in hairsprays is mentioned; however, the films obtained with these polyurethanes cannot in practice be used for hair cosmetology since they are either insoluble in water or have an inadequate molecular weight and therefore an insufficient setting effect.
DE-A-42 25 045 describes the use of water-soluble or water-dispersible anionic polyurethanes as hair lacquers. These polyurethanes are composed of
a) at least one compound containing two or more active hydrogen atoms per molecule,
b) at least one diol containing acid groups or salt groups, and
c) at least one diisocyanate.
They have a glass transition temperature of at least 15° C. and an acid number of 12-150. Preferred components a) employed are polyethylene glycol, neopentylglycol and polyesterols. Preferred components b) are dimethylolpropanoic acid, a condensation product of pyromellitic dianhydride and neopentylglycol, and a condensation product of 5-sodium-sulfonatoisophthalic acid with neopentylglycol.
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 a film former in hair lacquers, and are composed of
a) at least one diisocyanate which can 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 number of 50-200, based on the nonquaternized or protonated compounds.
EP-A-619 111 describes the use of polyurethanes containing carboxylate groups in hairsetting compositions. To provide the carboxylate groups the polyurethanes comprise a compound of the formula
in which A is hydrogen or C
1
-C
20
-alkyl. At least some of the carboxylic acid groups are then neutralized with an organic or inorganic base in order to provide the number of carboxylate groups required to render the polyurethane soluble in water or in a mixture of water and a polar organic solvent.
Hairsetting compositions are generally applied to the hair by spraying in the form of aqueous-alcoholic solutions. After solvent evaporation, the hair is held in the desired shape at the points of mutual contact of the residual polymer. The polymers should be sufficiently hydrophilic to enable washoff from the hair but sufficiently hydrophobic for the polymer-treated hair to retain its shape, even in the case of high atmospheric humidity, and for the individual hairs not to stick to one another. For a maximum hairsetting effect it is additionally desirable to employ polymers with a relatively high molecular weight (K value>25) and a relatively high glass transition temperature (at least 15° C.). However, the higher molecular weight of polymers meeting these requirements reduces the ease of washoff.
When formulating hair lacquers, another factor to consider is that a reduction in the content of alcohol and of propellent is necessary owing to environmental regulations regarding the control of the emission of volatile organic compounds (VOCs) into the atmosphere.
The polymers described in the abovementioned publications go only part way to meeting these contradictory requirements. For instance, although the high molecular weight of the polymers described in DE-A-42 25 045 and 42 41 118 and in EP-A-619 111 give them the desired setting effect, they are not sufficiently easy to wash off. The polymers described in U.S. Pat. No. 4,743,673, in turn, because of the low molecular weight which they have as a result of hydrolysis of the ester groups, do not possess the required setting effect.
EP-A-636 361 describes cosmetic compositions which include as a film former a polycondensation product comprising at least one polysiloxane unit and at least one polyurethane unit and/or polyurea unit having anionic or cationic groups. The ease of washoff of these film formers is also not satisfactory.
It is therefore the object of the present invention to provide hair treatment compositions which can be used as hair lacquers but which also have improve ease of washoff (redispersibility).
We have found that this object can be achieved, surprisingly, by means of water-soluble or water-dispersible polyurethanes which are the reaction product
Kim Son Nguyen
Sperling Karin
BASF - Aktiengesellschaft
Keil & Weinkauf
Sergent Rabon
LandOfFree
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