Hair treatment composition

Details Hair treatment composition Hair treatment composition

1998-04-29

2002-04-09

Page, Thurman K. (Department: 1615)

Drug, bio-affecting and body treating compositions

Live hair or scalp treating compositions

Polymer containing

C424S070100, C424S070110, C424S070120

Reexamination Certificate

active

06368583

ABSTRACT:

The present invention relates to hair treatment compositions and, in particular, to hairsetting compositions in the form of a hairspray.
Water soluble or water dispersible polymers, for example polyesters, polyamides or polyurethanes, are becoming increasingly important owing to their particularly low viscosity in water and in water/ethanol. For instance, water soluble polyurethanes which contain copolymerized carboxyl containing diols are known from U.S. Pat. Nos. 3,412,054 and 3,658,939. They are used as adhesives, as coating compositions and in printing inks. Polyurethanes containing sulfonate groups and/or carboxylate groups, which are dispersible in water, are known from DE-A-15 70 615. They are used, for example, for the coating and for the impregnation of textiles, leather, paper, wood and metals. Protective rights 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 NaSO3 groups and whose main chain is synthesized by condensation reaction, and which can be broken down into shorter segments by hydrolysis of 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 carboxylate groups, thereby obtaining solubility in water. From DE-A-26 37 167 and U.S. Pat. No. 3,523,998 it is known that polycarboxylic acids and their anhydrides, as well, may also contribute, as polymer components, to rendering polyesters soluble in water. A cosmetic application of such polymers, however, has not hitherto been described.
In cosmetology, film former polymers are used for setting, shaping and improving the structure of hair. The hair treatment compositions generally include 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 containing carboxyl groups in the polymer backbone. These polyurethanes are synthesized from a polyol component, which may 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, attached to the polymer backbone, ester groups which are subsequently hydrolyzed by heating under reflux for from 30 to 60 minutes with a strong base, such as sodium hydroxide or potassium hydroxide. The product obtained is no longer soluble either in water or in ethanol to give a clear solution. It is no longer soluble in water but is only soluble in lower aliphatic alcohols and other solvents. In particular when a polyesterdiol is used as polyol component, the treatment with the strong base under reflux conditions results in hydrolysis not only of the ester groups of the carboxylic ester component but also of the ester groups present in the polyurethane chain. There is therefore cleavage of the polyurethane chain and a drastic decrease in the molecular weight of the polyurethanes. Use of the polyurethanes in hairsprays is indeed mentioned; however, in practice the films obtained with these polyurethanes are unusable for hair cosmetology, since they are either insoluble in water or possess too low a molecular weight and therefore 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 transition temperature of at least 15° C. and acid numbers from 12 to 150. As component a), polyethylene glycol, neopentylglycol and polyesterols are preferably employed. 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 film formers in hair-setting 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 possess a glass transition temperature of at least 25° C. and an amine number of 50 to 200, based on the nonquaternized or protonated compounds.
EP-A-619 111 describes the use of polyurethanes containing carboxylate groups in hairsetting compositions. As a compound which provides the carboxylate groups, these polyurethanes include a compound of the formula
where R is hydrogen or C
1
-C
20
alkyl. At least some of the carboxylic acid groups in this case are neutralized with an organic or inorganic base in order to provide the number of carboxylate groups necessary to render the polyurethane soluble in water or in a mixture of water and a polar organic solvent.
EP-A-636 361 discloses cosmetic compositions comprising a film-forming polymer with at least one polysiloxane moiety and at least one polyurethane and/or polyurea moiety which contains anionic or cationic groups. Because of the siloxane moiety, the films are smoother, result in better grip and the hair becomes smoother in comparison to nonsiloxane-containing polymers. In analogy to the mentioned polyurethanes, the ease of washing out of these siloxane-containing film formers is not satisfying either, if the K value >24. However, if the K value is lower than 24, the ease of washing out is acceptable, but the fixing effect is insufficient.
It is further known to add a silicone compound (frequently polydimethylsiloxane; CTFA name: Dimethicon, e. g. Abil 10-100 000, Goldschmidt Company) during the formulation of hair treatment compositions, for example of hair spray. Due to the distinct hydrophobic character of the products, they have a positive effect on the film characteristics of the hair treatment composition. However, due to being highly hydrophobic, the polysiloxanes are very poorly soluble in water as well as ethanol. Phase separation from an ether water solution results in the film being turbid and unevenly distributed. Thus the hair is poorly leachable and an insoluble silicone residue remains on the hair, i. e. the hair is heavy and “greasy”.
Hairsetting compositions are generally sprayed onto the hair in the form of aqueous alcoholic solutions. After the evaporation of the solvent, the hair is held in the desired shape at the points of mutual contact of the polymer which remains. The polymers should on the one hand be sufficiently hydrophilic that they can be washed out of the hair but on the other hand should be hydrophobic, so that the polymer-treated hair retains its shape, even in the case of high atmospheric humidity, and there is no sticking together of individual hairs. In order to obtain a hairsetting effect of maximum efficiency, it is additionally desirable to employ polymers which possess a relatively high molecular weight (K value >25) and a relatively high glass transition temperature (at least 15° C.). Polymers which meet these requirements, however, are more difficult to wash out owing to the relatively high molecular weight.
Another factor to be taken into account when formulating hairsetting compositions is that a reduction in the content of alcohol and propellant is necessary owing to the environmental provisions for controlling the emission of volatile organic compounds (VOCs) into the atmosphere.
The polymers described in the abovementioned publications go o

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