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Publication numberUS2787274 A
Publication typeGrant
Publication dateApr 2, 1957
Filing dateDec 26, 1952
Priority dateDec 26, 1952
Publication numberUS 2787274 A, US 2787274A, US-A-2787274, US2787274 A, US2787274A
InventorsGant Virgil A, Hersh Hermann I
Original AssigneeHersh
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Ammonium polysiloxanolate hair treating composition and method for using same
US 2787274 A
Abstract  available in
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Description  (OCR text may contain errors)

i nited States Patent AMMONIUM POLYSILOXANOLATE HAIR TREAT- ING COMPOSITKON AND METHOD FOR USING SAME Virgii A. Gant, Oak Park, and Herman I. Hersh, Evanston Eli, assignors, by theme assignments, to said Hersh No Drawing. Application December 26, 1952, Serial No. 328,145

5 Claims. (Cl. 132-7) This invention relates to the treatment of hair on the human head and to compositions for use in same. it relates more particularly to compositions and methods for straightening kinky hair or for curling hair in the event that it is straight or has become straightened and to provide improvements in the characteristics and in the appearance of the treated hair.

In the copending application of Virgil A. Gan t, Ser. No. 263,509, filed on December 26, 1951, and now Patent No. 2,643,375, issued June 23, 1953, and in the copending application of Virgil A. Gant, Ser. No. 285,330, filed on April 30, 1952, and now Patent No. 2,750,947, issued June 19, 1956, description is made of a new and improved composition formulated to contain an orgariosilicon resinous material in an intermediate or in an advanced stage of polymeric growth, alone or in combination with an organo-silicon fluid or other lubricant for application in solvent solutions or from aqueous dispersions onto the hair fibers to improve the condition and the characteristics thereof. The organo-silicon resinous material is set on the hair fibers by thermal reaction in the event that the organo-silicon is in an intermediate stage of polymeric growth or else set by reaction in the presence of a catalyst alone or in combination with heat, or else the organosilicon resinous material may be set on the hair fibers merely by elimination of the diluent in the event that the compound is incorporated in an advanced stage of polymeric growth.

The formed organo-silicon compounds are stable at elevated temperatures and provide a substantially colorless component on the hair fibers which effectively hold the hair fibers in position upon setting of the organo-silicon material. It has been found that the organo-silicon compounds are incapable of harmfully affecting the hair structure or the scalp skin associated therewith and are therefore easy and safe to handle for purposes of hair conditioning. When the organo-silicon resinous materials are used in combination with an organo-silicon fluid or other lubricant, the latter functions effectively to improve the softness and sheen of the hair fibers thereby markedly to improve the appearance of the hair and to lessen the stiffness of the hair with the result that the hair fibers soon lose their natural kinky tendencies and ultimately acquire a soft and silky feel. Quite unexpectedly, the organo-silicon compounds, whether in the form of a resinous component alone or in combination with the organo-silicon fluids, seem to impart marked life and Vigor to the hair fibers without imparting any of the oily and greasy characteristics resembling constituents which have heretofore been used for hair straightening.

In the copending application of Hersh et al., Ser. No. 289,908, filed on May 25, 1952, description is made of an improvement in a hair straightening composition of the type described wherein the organo-silicon compound is provided in the form of a Silane having groups which hydrolyze readily upon addition of moisture to cause the immediate formation of lpolysiloxanes on the hair fibers 2,787,274 Fatented Apr. 2-, 1957 whereby hair setting and conditioning is achieved. The improvement described and claimed in said copending application makes it possible to achieve hair conditioning Without the use of heat for hair setting. The formation of the polysiloxanes on the hair fibers occurs as an incidence to the reactions which take place upon the addition of moisture for hydrolyzation of the silane followed substantially immediately by polymerization to form the polysiloxane on the hair fibers while the hair is being combed or has been set to a desired condition.

One of the objectionable features of compositions of the types previously described resides in the use of solvent medium for solution of the silanesor polysiloxanes. Such i solvent substances constitute a hazard in the use of the material for hair setting and present a barrier to the shipment of such. materials from station to station. In addition, the solvent component, present in high proportion in the hair treating composition, represents a major item in the cost of the hair conditioner and provides an odor which is dificult sometimes completely to eliminate.

Therefore, it is an object of thisinventio'n to provide a hair treating composition of the type described in which the organo-silicon compounds are contained in a stable aqueous system and it is a related object to provide a method for the use of same in the treatment of hair.

Another object is to provide a hair treating composition of the type described in which water constitutes the major diluent; which is stable in storage and use so as to prevent separation or deterioration of the hair treating composition upon storage; which is easy to prepare and which is safe and easy to apply onto the hair fibers for hair conditioning; which is safe to handle and ship and which is substantially free of odor and the ability to impart color.

It has been found, in accordance with the'practice of this invention, that an aqueous hair treating composition of the type described may be prepared with the desired organo-silicon compounds when such compounds are present in the form of water soluble polysiloiranolates. As used herein, the term polysiloxanolates is intended to include the polymers corresponding to the organo-silicon fluids, organo-silico'n resins and rubber-like materials but in which one or more of the hydroxy groups formed by hydrolyzation of hydrolyzable groups in the silane or otherwise contained in the organo-silicon compound are reacted to form a salt with an alkali metal or ammonia to form the corresponding alkali metal or ammonium polysiloxanolate which are Water soluble. A polysiloxanolate of the type described may be formulated by the general formulae in which M is an alkali metal such as sodium, potassium, lithium and the like or ammonium. Water soluble polysiloxanes may be prepared by reaction to hydrolyze and polymerize the silanes in the presence of an alkali metal base or ammonium hydroxide solution For other methods of manufacture and for suitable compounds for use in the practice of this invention, reference may be had to the United States Patents No. 2,472,799, issued on 3 June 14, 1949, and No. 2,567,110, issued on September 4, 1951.

While the water soluble alkali metal polysiloxanolates may be used, it is preferred to make use of the ammonium salts since insolubilization of the polysiloxane on the hair fibers takes place substantially automatically as an incidence to the drying of the composition On the hair fibers followed by volatilization of ammonia. In addition, the use of ammonium salts permits the application of compositions having a lower pH such as within the range of less than 10 down to a pH of about 5. Best use is made of ammonium polysiloxanolates in an aqueous treating composition adjusted to a pH of about 6 to 8.5. Instead of ammonium, other amine salts of the polysiloxanes may be used.

When the alkali metal polysiloxanolates are used, an after treatment to eliminate the metallic components and to insolubilize the polysiloxane on the hair fibers may be effected by wetting the hair fibers coated with the polysiloxanolate with an acidic medium and rinsing the hair as an incidence to or subsequent to the acidification to remove the salts which are formed. Acidification may be carried out with organic acids of the type formic acid, acetic acid, propionic acid, citric acid or the like, or dilute solutions of inorganic acids or acid salts such as ammonium chloride and the like.

It will be apparent from the description that the polysiloxanolates may be formed of low molecular Weight polymers generally having the characteristics of a polysiloxane fluid or lubricant or of higher molecular weight polymers generally having the characteristics of a resin or rubber-like material. Thus by proper selection of polymers, compositions may be formed which contain a desired balance between a low molecular weight substance for imparting lubricity and softness to the hair and a higher molecular weight substance which is believed to provide the hair conditioning properties, as defined in the copending applications of Virgil A. Gant previously referred to. While it is preferred to make use of a mixture of low molecular weight polysiloxanolates and high molecular weight polysiloxanolates in the ratio of about 0.1 to 3 parts by weight of the former to about 0.5 to parts by weight of the latter, the polysiloxanolate fluids or low molecular weight polymers may be dispensed with entirely when the higher molecular weight substances are capable of imparting some lubricity to the hair fibers and are present in amounts sufiicient to give hair setting but insufiicient to cause hair stiffening or embrittlement and insufficient to cause matting.

If more than 5 percent by weight of the high molecular weight polysiloxanolates is used, an undesirable matted or bonding relation would result with most hairs and the hair might become stiffened to a point where breakage would be possible. it is known that some hair fibers will tolerate greater amounts of the high molecular weight polysiloxanolates but amounts in excess of 10 percent by weight have not been found to be practical. When used within the amounts prescribed, the hair shafts can be properly guided to the desired set condition in a simple and expedient manner.

It is important to achieve rapid and complete wetting out of the hair fibers by the applied polysiloxanolates in order to achieve uniform distribution and prevent the formation of excessive concentrations in certain areas which might lead to stiffening or matting. Since most hair naturally acquires a film of oil upon the surfaces thereof, it is preferred to wash the hair immediately in advance of treatment but in any event to make use of a surface active agent imparted either to the hair fibers directly or incorporated with the organo-silicon treating composition. As the wetting agent or surface active agent of the type described, it is desirable to select a compound which is stable, which has little if any color and which is compatible with the system in which the organesilicon compounds are formulated.

Use may be made of aryl alkyl polyether alcohols, such as are marketed by Rohm and Haas Company under the trade name Triton X- or by the Atlas Powder Company under the trade name Tween, or sorbitan monolaurate, monopalmitate, or monostearate, or polyoxyethylene derivatives. Instead, other commercially available materials such as polyglycol esters, dioctyl ester of sodium sulfosuccinate, alkyl naphthalene sulfonate, sorbitan, sulfooleate, fatty alcohol sulphates, aromatic polyglycol ethers, sodium di(2-ethyl-hexyl) phosphate, and the like may be used. The amount of wetting agent, when used to enhance the wetting out properties, may range from 0.05 to 2.0 percent by weight of the treating composition. More may be used when desired but such amounts have usually been found to be snfiicient.

The following examples are given by way of illustration, but not by way of limitation, of hair treating compositions embodying features of this invention:

Example 1 15 percent by weight of ammonium polysiloxanolate formed of a copolymer of phenyl ethyl siloxane struc tural units and phenyl siloxane structural units 0.52 percent by weight of a lubricant 0.05-1 percent by weight of a wetting agent 0-0.4 percent by weight of a perfume oil Remainder Water The composition is adjusted to a pH of about 7.5 with ammonia.

Example 2 l-3 percent by weight of ammonium polysiloxanolate in the form of a copolymer consisting of phenyl methyl siloxane and diphenyl methyl siloxane structural units 0.52 percent by weight of an ammonium dimethyl polysiloxanolate fluid 0.1-0.5 percent by weight of a wetting agent Remainder water Example 3 3.0 percent by weight of a copolymer of dimethyl, phenyl and methyl polysiloxanolate in the form of a water soluble salt 0.5 percent by weight of sodium diphenyl polysiloxanolate 0.1 percent by weight of sorbitan monolaurate polyoxyethylene derivative wetting agant 0.1 percent by weight of a perfume oil Remainder being water adjusted to a pH of between 7-9 Example 4 2.0 percent by weight of an ammonium polysiloxanolate resin in the form of a copolymer of phenyl ethyl, phenyl and ethyl polysiloxanes Remainder being water having a pH of about 6 Example 5 2.5 percent by weight of sodium polysiloxanolate formed of the copolymer of phenyl, methyl and phenyl methyl polysiloxanes I 1 percent by weight mineral oil 0.2 percent by weight di(2-ethyl-hexyl) phosphate wetting agent Remainder being water with the pH of the composition adjusted to about 7.5

After the hair has become dried from shampooing or the like, the treating compositions of Examples l-5 containing the polysiloxanolate compounds in aqueous solution are applied lightly to secure uniform coverage over sections of the hair. The section of hair which has been wet by the treating composition as by spraying or by padding or by other conventional wetting means is then straightened by the use of a metallic comb which may be heated to a temperature which exceeds 250 F. but is preferably maintained at a temperature below 400 F. to achieve the elimination of diluent and the removal of the salt forming component, if of ammonia, to set and insolubilize the organo-silicon compounds on the hair fibers. This may require merely two to three passes of the hot comb through the section of hair with the application of slight pressure to cause hair straightening before the organo-silicon compounds are set on the hair fibers. Kinky hair which has been straightened by this technique may be waved simply by wrapping a shock of the straightened hair about curlers and then heating in the usual manner employed for permanent waving without the requirement for the application of additional treating compositions.

After the hair has been straightened, the shocks of hair may be curled by pin curling technique or by the use of Croquignole waving irons. Hair which is naturally straight can be permanently waved by wrapping shocks of hair about curlers in the normal permanent waving technique, applying a composition corresponding to Examples 1-5 and then heating the treated hair for the usual length of time for driving off the diluent and setting the resinous material on the hair fibers. The time required for this process corresponds favorably with that generally employed in present permanent wave techniques.

Compositions of the type described and claimed herein may also be used to achieve hair conditioning without the use of hot combs or heated elements to achieve the more rapid volatilization of diluents and setting of the organo-silicon compounds on the hair fibers. Compositions of the type described and more specifically illustrated in Examples 1-5 inclusive may be applied onto sections of the hair as by spraying or by swabbing with a cotton pad followed by combing of the hair or otherwise positioning the hair into the arrangement desired until the Water or other diluent has been substantially completely eliminated by evaporation. Elimination of the water may be carried out under room conditions but it is accelerated by the use of elevated temperatures such as temperatures of about 100-150 F. Higher temperatures may be used so long as the temperature does not exceed that at which the hair will be harmed.

Upon drying, the organo-silicon compounds become set on the hair fibers and upon volatilization of the salt forming ammonium or amine compounds or neutralization of the alkali metal salt components, the material becomes insolubilized on the hair fibers so as to permanently retain the set condition.

Hair treated in the manner described may be further formed as by the finger-waving methods, curling irons, or permanent wave machines in the manner previously suggested for the hot comb compositions. If desired, oleagenous substances such as oils, waxes and the likc may be incorporated in the treating composition or applied to the hair afterwards to improve the sheen and softness of the hair.

When it is desired to make use of permanent waving techniques of the type now in use employing mild reducing agents of the type thioglycolic acid followed by the use of oxidizing agents to reform the hair molecules after the hair has been set, compositions of the type described and claimed herein may be used to achieve hair straightening so that such permanent waving compositions might subsequently be applied and used for permanent waving and the like. In the absence of suitable hair straightening, such permanent waving compositions are incapable of practical use for hair treatment.

This is a continuation-in-part of copending application Ser. No. 263,509, filed on December 26, 1951, and now Patent No. 2,643,375.

It will be understood that changes may be made in the compositions, their methods of application and in the methods of treatment to achieve hair conditioning without departing from the spirit of the invention, especially as defined in the following claims.

We claim:

1. A hair treating composition of the type described containing from 0.1 to 3.0 percent by weight of a water soluble ammonium polysiloxanolate of a liquid polymer and 0.5 to 5.0 percent by weight of a water soluble ammonium polysiioxanolate of a solid polymer.

2. The method of setting the hair on the human head comprising the steps of wetting the hair with an aqueous composition containing from 1 to 5 percent by weight of an ammonium polysiloxanolate, eliminating the water while the hair is being positioned in the arrangement in which it is to be set whereby the polysiloxanolate becomes set on the hair fibers as a water insoluble polysiloxane.

3. The method of setting the hair on the human head comprising the steps of treating the hair with an aqueous composition containing 0.1 to 3 percent by weight of an ammonium polysiloxanolate of a liquid polymer and 0.5 to 5 percent by weight of an ammonium polysiloxanolate of a solid polymer, setting the polysiloxanoiates as the corresponding polysiloxanes on the hair strands by elimination of the diluent and the cation while the hair is being positioned in the arrangement in which it is to be set.

4. The method of setting the hair on the human head comprising the steps of wetting the hair with an aqueous composition containing 0.1 to 3 percent by weight of an ammonium polysiloxanolate of a liquid polymer and 0.5 to 5 percent by weight of an ammonium polysiloxanolate of a solid polymer, heating the wetted hair to a temperature above 250 F. to eliminate the diluent and set the polysiloxanolate on the hair fibers as the corresponding water insoluble polysiloxane while the hair is being positioned in the arrangement in which it is desired to be set.

5. The method of setting the hair on the human head comprising the steps of wetting the hair with an aqueous composition containing 1 to 5 percent by weight of an ammonium water soluble polysiloxanolate, heating the wetted hair to a temperature above 250 F. to eliminate the diluent and set the polysiloxanolate on the hair fibers as the corresponding water insoluble polysiloxane while the hair is being positioned in the arrangement in which it is desired to be set.

References Cited in the file of this patent UNITED STATES PATENTS 2,507,200 Elliott May 9, 1950 2,587,636 MacMullen Mar. 4, 1952 2,643,375 Gant June 23, 1953

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2507200 *Feb 10, 1945May 9, 1950Gen ElectricProcess for rendering materials water-repellent and compositions therefor
US2587636 *Dec 31, 1948Mar 4, 1952Cowles Chem CoMethod of making alkali metal salts of organosiloxanols and organosilanetriols
US2643375 *Dec 26, 1951Jun 23, 1953Northwestern Res CorpMethod of treating hair
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US2944942 *Aug 1, 1957Jul 12, 1960OrealMethylsilyl mercaptoacetates and their use in treating hair
US2989365 *May 9, 1957Jun 20, 1961Nat Lead CoMethod for setting keratinous fibers
US3047535 *Sep 3, 1958Jul 31, 1962Bradford Dyers Ass LtdMetal salts of substituted phosphoric acid as curing agents for polysi-loxanes
US3057821 *Aug 26, 1958Oct 9, 1962 Ammonium halide stabilized organo-
US3568685 *Apr 15, 1968Mar 9, 1971Howard L ScottTreating human, animal and synthetic hair with a water-proofing composition
US3949764 *Nov 3, 1970Apr 13, 1976Fabalon, Inc.Treatment of natural and synthetic hair with a heat-settable composition
US4115549 *Apr 13, 1976Sep 19, 1978Widner CollegeCoating the hair with a heat-settable composition
US4586518 *Aug 6, 1984May 6, 1986Dow Corning CorporationHair setting method using aminoalkyl substituted polydiorganosiloxane
US4770873 *Feb 25, 1986Sep 13, 1988Clairol, IncorporatedNeutralizing composition and method for hair waving and straightening
US4985240 *Feb 20, 1990Jan 15, 1991Dow Corning CorporationOdor-free perm
US7740664Jun 22, 2010L'oreal S.A.Composition comprising at least one silicone compound and at least one organosilane
US7780742Aug 24, 2010L'oreal S.A.Composition comprising a compound X and A compound Y, at least one of which is a silicone, and a hydrophobic direct dye
US20080172807 *Dec 20, 2007Jul 24, 2008Gaelle BrunTreatment of hair fibers with a composition comprising reactive silicone compounds, before or after a dyeing method
US20080184496 *Dec 20, 2007Aug 7, 2008Gaelle BrunComposition comprising a compound X and A compound Y, at least one of which is a silicone, and a hydrophobic direct dye
US20080226577 *Dec 19, 2007Sep 18, 2008L'orealCosmetic product comprising silicone compounds and an amphiphilic polymer
US20080254077 *Dec 19, 2007Oct 16, 2008L'orealCore/shell particles based on silicone compounds
US20080289647 *Dec 20, 2007Nov 27, 2008Gilles GenainProcess for treating hair fibres with compositions containing reactive silicones
US20080292572 *Dec 19, 2007Nov 27, 2008Katarina BenabdillahProduction of structured hairstyles using a composition comprising reactive silicone compounds
US20080292573 *Dec 18, 2007Nov 27, 2008Franck GiroudMethod for treating hair with a reactive vinyl silicone capable of reacting via hydrosilylation
US20090183320 *Jul 23, 2009Katarina BenabdillahComposition comprising at least one silicone compound and at least one organosilane
US20090214455 *Dec 20, 2006Aug 27, 2009Xavier BlinProcess for making up or caring for keratin materials, comprising the application of compounds a and b, at least one of which is silicone-based
US20090260165 *Oct 22, 2009Gaelle BrunComposition comprising a compound X and A compound Y, at least one of which is a silicone, and a hydrophobic direct dye
US20090317348 *Dec 24, 2009Katarina BenabdillahProduction of structured hairstyles using a composition comprising reactive silicone compounds
EP1974772A1 *Dec 14, 2007Oct 1, 2008L'orealAchievement of structured hairstyles using a composition containing reactive silicone compounds
Classifications
U.S. Classification132/206, 132/202, 424/70.12
International ClassificationA61K8/72, A61K8/891, A61Q5/06, A61K8/898
Cooperative ClassificationA61K8/898, A61Q5/06
European ClassificationA61Q5/06, A61K8/898