US2782790A - Hair treating composition and methods for use of same - Google Patents

Description

United States Patent HAIR TREATING CGMPGSITION AND METHODS FOR USE OF SAME Herman I. Hersh, Evanston, and Frank P. Bessing, Chigigo, 111., assignors, by mesne assignments, to said ersh N 0 Drawing. Application May 24, 1952, Serial No. 289,908

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

In the copending application of Virgil A. Gant, Serial No. 112,186, filed on August 24, 1949, now abandoned, and in the copending applications of Virgil A. Grant, Serial No. 263,509, filed on December 26, 1951 now Patent No. 2,643,375, and Serial No. 285,330,,filed on April 30, 1952 now Pat. No. 2,750,947, description is made of a new and improved composition formulated to contain an organo-silicon resinous material in an advanced or intermediate 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 in the treatment of hair on a human head. The organo-silicon resinous material is set in situ on the hair fibers by thermal reaction in the event that the resinous material is applied in an intermediate stage of polymeric growth or such resinous material may be set by reaction in the presence of a catalyst or in the presence of a catalyst in combination with heat or else the organo-silicon resinous material may be set on the hair fibers by elimination of the diluent in the event that the organo-silicon is embodied in the hair treating com position in an advanced stage of polymeric growth.

The formed resinous materials are stable at elevated temperatures and provide a substantially colorless medium on the hair fibers which in set condition effectively hold the hair fibers in positions to which they are held during setting of the resinous material. The organosilicon substances are incapable of any deleterious effect on the hair structure or scalp skin associated therewith and are therefore easy and safe to handle for purposes of hair conditioning. The organo-silicon resinous material when used in combination with an organo-silicon fluid or other lubricant 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 characteristics and ultimately acquire a natural soft and silky feel.

To the present, the setting of the organo-siliconresinous material has required the use of heat, such as from hot combs, either to accelerate the elimination of diluent in the event that the organo-silicon is in advanced stage of polymeric growth or else to eliminate the diluent and react the resinous component, alone or in combination with a catalyst, in the event that the organo-silicon is applied in an intermediate stage of polymeric growth. Although the Negro is accustomed to the use of hot combs for setting such materials as oil-s, greases, phenol formaldehyde resin compositions and the like to achieve hair setting and although hot wave systems have been used for purposes of curling, it is desirable to provide "ice compositions capable of use Without the application of heat to achieve the desired results.

Therefore it is an object of this invention to provide a method for conditioning hair in the absence of heat and it is a related object to provide new and improved compositions for use in same.

Another object is to produce a new and improved hair conditioning composition which may be used with or without the application of heat and it is a related object to provide new and improved methods for use of same in hair conditioning.

A further object is to produce a composition which is safe and easily applied in use for conditioning hair on the human head and it is a related object to provide a new and simple method for rapidly conditioning hair in an economical and safe manner.

It has been found, in accordance with the practice of this invention, that an organo-silane having at least two readily hydrolyzable groups attached directly to the silicon atom may be applied to the hair on the human head in non-aqueous medium without modification of the organo-silane and that before, but preferably after, elimination of the diluent with which the organo-silicon is applied, the organo-silane may almost immediately be hydrolyzed to the corresponding silanol and condensed to an organo-silicon polymer in situ on the hair fibers merely by the application of moisture thereby to condition the hair fibers in the manner described in the absence of heat.

It is possible in accordance with the practice of this invention to divide the hair into sections on the human head for treatment with the composition containing the organo-silane followed by wetting, as by combing or by spray means or the like in the event that hair straightening or hair curling is to be effected. With compositions of the type embodied in this invention it is, however, preferred to apply the composition to coat the hair fibers over the entire head and then comb or brush the hair at room temperature with a hair brush or comb dampened or wetted with water. The formation of the organo-silicon resin during straightening of the hair with a brush or comb, as in the usual manner, will have the eifect heretofore achieved by hot combing with an organo-silicon polymer requiring heat to set the organesilicon on the hair fibers. Compositions of the type described herein provide for further simplicity in hair setting in that the entire head of hair may be treated with the necessary amount of composition and then set at room conditions to the desired arrangement. Thereafter, set conditions may be caused to become pennanent by wetting the head of hair as by a rinse, damp towel, vapor spray, wet brush or absorbent pads or the like.

It has been found further that after the hair has been conditioned such as to straighten kinky hair, the organosilicon formed on the hair fibers permits further setting of the hair in pin curls or the like by hot waving technique or other conventional curling operations without the application of additional materials.

As used herein, the term organo-silane is meant to include hydrolyzable organo mono-silanes having the general formula type methyl, ethyl, propyl, isopropyl, butyl, hexyl, octadecyl, undecyl or larger fatty acid radicals; alicyclic radicals such as cyclopentyl, cyclohexyl and the like; aryl and alkyl radicals of the type phenyl, alkyl phenyl, such as tolyl, xylyl, rnesityl, triethyl phenyl, diethyl phenyl; naphthyls such as mono and polyalkyl naphthyls like methyl naphthyl, diethyl naphthyl, tetrahydro naphthyl; anthracyl, aralkyl such as benzyl, phenyl, ethyl and the like; alkenyl such as methallyl vinyl, allyl and the like, and heterocyclic radicals and derivatives thereof such as are formed with chlorine, bromine, sulfonic and other substituent groups. X represents groups such as the halogens of the type chlorine, bromine, amino groups, alkoxy groups, acyloxy groups and aryloxy groups of relatively low carbon content such as methoxy, ethoxy and the like short chain groups readily hydrolyzable from the silicon atom in aqueous medium to form corresponding hydroxy compounds capable of condensation with other hydroxy groups or hydrolyzable groups to form polymers, with or without catalysts, such as acid or alkalis.

When the organo-silicon monomer of the hair treating composition contains two available hydrolyzable groups, hydrolyzation and substantially simultaneous condensation occurs in aqueous medium to form relatively straight chain polymers of a relatively soft and resilient character capable of setting the hair in positions held during organo-silicon polymerization while permitting resetting of the hair to desired configuration by subsequent application of heat or the like. When the organo-silanes in the treating composition are formed of a mixture of compounds having two hydrolyzable groups with a few compounds having three available hydrolyzable groups, a polymer is formed upon hydrolyzation and condensation having the characteristics of an elastomer whereby the hair particles remain highly flexible and embody a soft and silky appearance but are capable of maintaining hair setting conditions even in the presence of high humidity. As with the resinous materials formed with silanes having two hydrolyzable groups, the formed polymer permits resetting of the hair into pin curls or other configurations by the use of heat soon after resin formation. In the event that the organo-silane of which the hair treating composition is formed contains three available hydrolyzable groups, then cross-linked polymers are formed which are thermosetting in nature to provide for hair setting in a substantially more permanent manner.

Of the organo-silicon polymers formed in situ on the hair fibers -by hydrolyzation and polymerization while holding the hair in position for setting, some of the polymers are liquids formed by the combination of a smaller number of building units while others are solids of a waxy, rubber-like or resinous nature formed by considerably larger numbers of building units before polymerization is blocked. Those which are completely blocked against further polymerization are relatively heat stable but others are capable of further condensation and hardening upon the application of heat and/or catalyst but, in any event, suflicient polymers of solid character are produced by the initial hydrolyzation and polymerization to set the hair fibers. The polymers of low molecular weight function as lubricants in the final product to impart lubricity to the hair fibers and improve their luster and sheen and general overall appearance.

The character of the organo-silicou polymer formed depends not only upon the number of hydrolyzable groups available in the organo-silane but also on the character of the organic groups. Where the organic groups are of the low aliphatic series or aromatic groups, a harder product is formed which requires some lubricant to enhance the lubricity and softness as well as to improve the feel of the hair fibers while organic groups of the higher fatty acid radicals tend to produce polymers which are softer and more flexible in nature and therefore require less lubricant to achieve the desired characteristics. Thus in the practice of this invention, it is desirable to balance the silanes with respect to the number of hydrolyzable groups to control the polymer structure between liquid polymers of low molecular weight and harder polymers of high molecular weight and cross linking and also preferably to provide for a balance between silanes of long chain fatty acid groups such as diotadecyl diethoxy silane which form soft and flexible lubricating polymers and silanes of short chained organic radicals such as with methyl, ethyl, and phenyl groups which produce harder solids of resinous nature.

As previously pointed out, a certain proportion of lower molecular weight polymers are formed which are liquid in nature and capable of functioning as a lubricant in the resulting product. Where the amount of lubricant formed is insuflicient to prevent matting or to impart the desired lubricity and silky softness to the hair, additional lubricants in the form of an organo-silicon fluid, such as dimethyl polysiloxane (DC 200 fluid) or diethyl polysiloxane (DC 400 fluid) or diphenyl polysiloxane (DC 500 fluid) or dilauryl polysiloxane (DC 1500 fluid) may be used. Where the fluid formed is suflicient to impart the desired lubricity and softness to the hair fibers but the amount of resinous material is insufficient to achieve hair setting, the treating composition may be formulated to contain additional amounts of an organosilicon resin of the type phenyl methyl, phenyl and methyl polysiloxane, dimethyl and phenyl polysiloxane, diphenyl, methyl polysiloxane and the like.

Generally it is desirable to formulate the treating composition to produce a polymer by hydrolyzation and polymerization having a maximum of about 5 percent of a polymer which is solid in nature and a maximum of about 5 percent of a polymer which is fluid in nature. Generally when the solid polymers exceed 5 percent, hair stiflening occurs with the possibility of experiencing ha-ir breakage and the hair becomes matted in a manner to prevent combing. However, more than the 5 percent polymeric solids can be tolerated when calculated on the basis of the treating composition if the amount of lubricant is greatly increased to provide for greater lubricity and overcome the possibility of hair breakage and matting but it is desirable to formulate the composition not to exceed 8 percent polymeric solids formed thereof, calculated on the basis of the treating composition. Generally lubricants in amounts up to about 1 to 3 parts by weight to 5 parts by weight high polymeric solids are preferred but the lubricant can be completely eliminated if polymers of a flexible nature are produced.

In general, the desired ratio of polymeric solids and fluids will result quite naturally by normal hydrolyzation and polymerization of the organo-silanes. As a result, a treating composition containing 3 to 10 percent by weight silane may be used in accordance with the practice of this invention, depending of course upon the organic groups of which the silane is formed and the number of hydrolyzable groups available for hydrolyzation and polymerization.

When additional lubricant is required to make up the desired proportions, instead of the organo-silicon fluids of the type described, other lubricants soluble in the diluent for the organo-silane may be used, such for example as mineral oils, palm oil, olive oil, vegetable oils and the like, fatty acids, fatty acid amines and the like, waxes and other conventional lubricating substances of the type described in the copending application of Virgil A. Gant, Serial No. 285,330.

It is desirable to secure uniform distribution of the treating composition over the entire lengths of hair in order to avoid undesirable concentrations in certain areas which might cause matting or stiffening. Most hair acquires a film of oil on the outer surfaces thereof which often presents a barrier to the desired wetting out of the fibers and it is desirable, on that account, to incorporate a small amount of wetting agent or surface active agent in the treating composition. In the event that the hair is thoroughly washed prior to treatment, such wetting '5 agents may be eliminated. As a wetting agent it is desirable to select a compound that is stable and which has little, if any, color and which is compatible with the system in which the organo-silane is contained.

It is preferred to make use of aryl alkyl polyethyl alcohols such as are marketed by Rohm & Haas under the trade name Triton X100 or marketed by Atlas Powder Company under the trade name Tween. Use may also be made of sorbitan monolaurate, monopa'lmitate, monostearate polyoxyethylene derivatives or other commercially available materials such as thepolyglycol esters represented by dioctyl ester of sodium sulfosuccinate or the alkyl naphthalene sulfonates, sorbitan sulfooleates, fatty alcohol sulphates, aromatic polyglycol ethers and the like. The amount of wetting agent may range from 0.05 to 2 percent by weight of the treating composition. Although more can be used, the amount specified is sufficient.

The following formulations are representative of compositions which may be used in the practice of this invention:

Example 1 5.0 percent by weight methyl dimethoxy silane 2.0 percent by weight ethyl tr-imethoxy silane 0.2 percent by weight ammonium hydroxide 43.0 percent by weight xylene 49.8 percent by weight kerosene Example 2 Example 3 6.0 percent by weight triethoxy phenyl silane 2.0 percent by weight polysiloxane fluid (DC 200) 0.5 percent by weight sorbitan monolaurate polyoxyethylene derivative wetting agent 91.5 percent by weight solvent Example 4 4.0 percent by weight ethyl trimethoxy silane 2.0 percent by weight didocyl dichlor-o silane 94.0 percent by weight solvent Example 5 2.0 percent by weight dimethyl diethoxy silane 2.0 percent by weight methyl dichloro silane 2.0 percent by weight dilauryl diethoxy silane 2.0 percent by Weight phenyl and methyl polysiloxane resin 92.0 percent by weight solvent Example 6 5.0 percent by weight di-ethyl diethoxy silane 1.0 percent by weight methyl dichloro silane 2.0 percent by Weight DC 500 polysiloxane fluid 0.4 percent by weight wetting agent 45.8 percent by weight benzene 45.8 percent by weight xylene In operation, it is best to shampoo the hair thoroughly to eliminate dirt, grease and oil from the hair fibers. After drying, the treating composition of Examples 1-6 may be applied lightly to secure homogeneous coverage on small sections of hair by means of an atomizing spray or cotton swab, or distribution may be achieved by pouring onto certain areas and working into the hair with the finger tips to achieve overall coverage at the same time. Upon drying or slightly before the diluent has been eliminated, the hair may be straightened with a comb or brush t tion of the silane =coating'the' hai-r fibers will take place to form organo-si'licon polymers capable of holding the hair in straightened condition. Such operations to achieve hair setting will take place in a matter of seconds to at the most a few minutes, depending upon the composition of the organo-s-ilane. The hair may be allowed to dry with or without continued combing whereby the hair retains its straightened condition and embodies an improved sheen and softness.

Kinky hair which has been straightened by this technique can be permanently waved simply by wrapping the straightened hair about curlers and then heating in the manner generally employed for permanent waving for a short length of time without requiring the application of additional treating composition. In the event that it is desirable to achieve hair curling without the application of heat, additional treating composition may be applied as the hair is held in pin curls or the like followed by wetting to achieve polymerization and hair setting. Hair which is naturally straight can also be permanently waved by wrapping about curlers in the normal permanent waving technique and then applying the treating compositions of Examples l-6 substantially uniformly to wet out the hair fibers. Thereafter, before or preferably after the elimination of the diluent, which may take a few minutes, the hair fibers while still being held in pin curls or the like may be wetted by a water spray, dampening pad or other moistening means to achieve polymerization of the organo-silane in the manner described whereby the hair fibers are permanently held in the curled arrangement and the organo-silicon formed on the surfaces thereof functions to render the hair fibers repellent to moisture whereby the configuration to which the hair fibers are formed remains substantially permanent under normal conditions. The moisture normally existing in the air is sufficient slowly to cause the desired hydrolyzation and polymerization thereby to achieve hair setting without the application of moisture, where as in curling technique, the hair may be set up in pin curls or the like and wetted with the treating composition either before or after setting and merely allowed to stand.

In the event that the treating composition is formulated to contain additional organic resinous material in an intermediate stage of polymeric growth, suitable catalysts may be incorporated into the treating composition, as described in the copending application of Virgil A. Gant, Serial No. 263,509, filed on December 26, 1951, whereby resin formation occurs at room conditions though at a slower rate than that which is formed by condensation and polymerization of the silanes contained in the treating composition.

A further improvement in treating compositions resides in the formulation of the silane to form a gel in combination with the organicsolvents whereby the composition may be applied to the hair in the form of a pomade to permit the composition to be worked into the hair to secure uniform distribution in desired concentrations on the hair fibers. Upon elimination of solvent or prior thereto, Wetting may be carried out in the manner previously described while forming the hair to the desired arrangement whereby hair setting will naturally occur. A composition representative of such pomade may be formulated of fillers capable of causing the solution to form into a gel such for example as by the addition of small amounts of aluminum hydroxide to the compositions of Examples 1-6. Usually l-l0 percent aluminum hydroxide is sufiicient to cause gel formation. Other substances capable of gel formation in compositions of the type described may be used or the hair may be allowed to set by reaction with the moisture in the air upon standing.

Since hydrolyzation'can be controlled by the character of the organic groups and the number and type of hydrolyzable groups on the silane, it is desirable to balance wetted with water whereby hydrolyzation and polymerizathe silanes for a cure rate of about l-5 minutes to give 7 sufiicient time for hair straightening in conjunction with polymer formation. Where catalysts are required to accelerate setting use may be made of the weaker acids and alkalies.

It is preferable to make use of silanes in which the hydrolyzable groups comprise oxy groups such as methoxy, ethoxy, phenoxy and the like because then the corresponding alcohols are relased upon hydrolyzation, otherwise acids would be released in the event that the hydrolyzable groups were halogens. However, where it is desirable to catalyze hydrolyzation and polymer formation, instead of incorporating acids or alkalies in the treating composition to accelerate the reaction, it is more expedient to embody some of the chloro silanes which rapidly hydrolyze and contain released acid in amounts sufficient to catalyze the polymerization of the oxy silanes or other silanes which might be present in dominant proportions.

As previously pointed out, the desired balance in lubricity and hair setting may be secured by proper combination of silanes in the treating composition. For example, a desired balance between resin formation and lubricating polymers can be secured by the combination of from 27 percent by Weight silanes having two or three hydrolyzable groups and organic groups attached directly to the silicon atom containing less than 6 carbon atoms in straight chain arrangement, or aromatic groups and from 1-4 percent by weight of silanes having two or three hydrolyzable groups and at least one organic group attached directly to the silicon atom and having a carbon chain containing more than carbon atoms, such for example as dodecyl trichloro silane, hexadecyl trichloro silane, octadecyl trichloro silane, dodecyl dichloro silane, octadecyl dichloro silane, dodecyl diethoxy silane, dodecyl triethoxy silane, octadecyl diethoxy silane and the like. Representative of the silanes of the first group are the dior tri-ethoxy, methoxy, chloro, or bromo silanes wherein the organic groups attached directly to the silicon atom are methyl, ethyl, n-propyl, butyl, phenyl, tolyl and the like. The following formulation broadly illustrates the concept of this phase of the invention:

Example 7 25 percent by weight diethyl diethoxy silane l-2 percent by weight methyl trimethoxy silane l-3 percent by weight hexadecyl dichloro silane 1 percent by weight wetting agent 0.5 percent by weight perfume oils 18.5 percent by weight Cellosolve percent by weight xylene 46-5 2 percent by weight kerosene It has also been found that hydrolyzation and polymerization to form the resin and lubricant can be controlled by formulation with silanes having certain hydrolyzable groups. For example, the oxy groups have been found to hydrolyze off at a much slower and controllable rate than the halogens and, in the case of the former, the product of hydrolyzation ,is an alcohol while acids are formed by the halogens further to catalyze the reaction whereby hydrolyzation and polymerization proceeds at a more rapid rate. The rate of hydrolyzation of the methoxy groups is also dependent upon the length of the oxy group. For example, methoxy groups hydrolyze off faster than ethoxy and so on. Thus by proper balance of oxy groups and of halogen groups in the silanes, it is possible to provide for setting rates ranging from a few seconds to several minutes. The following examples will illustrate this concept:

Example 8 A slow acting composition:

3-5 percent by weight phenyl triethoxy silane 1-2 percent by weight diethyl diethoxy silane 1-3 percent by weight octadecyl triethoxy silane 8 0.5 percent by weight wetting agent 0.5 percent by weight perfume oils Balance solvent Example 9 A more rapid acting composition:

24 percent by weight dimethyl dimethoxy silane l-2 percent by weight methyl trimethoxy silane 1-3 percent by weight dodecyl trichloro silane 1 percent by weight wetting agent 0.5 percent by weight perfume oils Balance solvent Example 10 A rapid acting composition:

l-4 percent by weight methyl trimethoxy silane l-2 percent by weight methyl trichloro silane l-3 percent by weight hexadecyl trichloro silane 1 percent by weight wetting agent 0.5 percent by weight perfume oils 1 percent by weight acetic acid Balance solvent Suitable solvents for the silanes may be selected of the hydrocarbons, the aromatic solvents, ethers and chlorinated solvents.

It will be understood that the treating composition embodying features of this invention may be formulated to contain small amounts of organo silanes having but one hydrolyzable group whereby the organo silane is capable of hydrolyzation and addition to the polymers formed but functions as a blocking group to control the length of the polymers.

It will be further understood that changes may be made with respect to the compositions of the materials, their ratio in the treating composition, and their method of application, without departing from the spirit of the invention, especially as defined in the following claims.

We claim:

1. The method of conditioning hair on the human head comprising the steps of wetting the hair with a nonaqueous composition containing a silane having attached to the silicon atom at least two but less than four hydrolyzable groups selected from the class consisting of alkoxy, aryloxy and acyloxy radicals and alkoxy, aryloxy and acyloxy radicals together with a halogen group selected from the class consisting of chlorine and bromine and from 1-3 percent by weight of a polysiloxane fluid, and moistening the hair with an aqueous medium while arranged in the desired position to cause hair setting.

2. The method of conditioning hair on the human head comprising the steps of wetting the hair with a nonaqueous composition containing 27 percent by weight of a silane having attached to the silicon atom at least two but less than four hydrolyzable groups selected from the class consisting of alkoxy, aryloxy and acyloxy radicals and alkoxy, aryloxy and acyloxy radicals together with a halogen group selected from the class consisting of chlorine and bromine and having connected directly to the silicon atom organic radicals containing less than 7 carbon atoms and from l-3 percent by weight of a silane having attached to the silicon atom at least two but less than four hydrolyzable groups selected from the class consisting of alkoxy, aryloxy and acyloxy radicals and alkoxy, aryloxy and acyloxy radicals together with a halogen group selected from the class consisting of chlorine and bromine and attached directly to the silicon atom organic radicals containing more than 10 carbon atoms, and moistening the hair with an aqueous composition while arranging the hair to the desired position for setting.

3. The method of conditioning hair on the human head comprising the steps of wetting the hair with a nonaqueous composition containing 27 percent by weight of asilane having attached to the silicon atom at least two but less than four hydrolyzable oxy groups and having connected directly to the silicon" atdm organic radicals containing less than 7 carbon atoms and from 1-3 percent by weight of a silane having at least two but less than four hydrolyzable my groups and attached directly to the silicon atom organic radicals containing more than carbon atoms, 'and moistening the hair with an aqueous composition while arranging the hair to the desired position for setting.

4. The method of conditioning hair on the human head comprising the steps of wetting the hair with a nonaqneous composition containing 2-7 percent by weight of a silane having attached to the silicon atom at least two but less than four hydrolyzable oxy groups and attached directly to the silicon atom organic radicals containing less than 7 carbon atoms and 1-3 percent by weight of a silane having at least two but less than four hydrolyzable groups and connected directly to the silicon atom at least one organic radical having more than 10 carbon atoms and less than 1 percent of a catalyst selected from the group consisting of acids and alkalies soluble in the non-aqueous medium, and moistening the hair with an aqueous composition while arranged in the desired position to cause hair setting.

5. The method of conditioning hair on the human head comprising the steps of wetting the hair with a nonaqueous composition containing 27 percent by weight of a silane having attached to the silicon atom at least two but less than four hydrolyzable groups selected from the class consisting of alkoxy, aryloxy and acyloxy radicals and alkoxy, aryloxy and acyloxy radicals together with a halogen group selected from the class consisting of chlorine and bromine and having attached directly to the silicon atom organic radicals containing less than 7 carbon atoms and 1-3 percent by weight of a silane having attached to the silicon atom at least two but less than four hydrolyzable groups selected from the class consisting of alkoxy, aryloxy and acyloxy radicals and alkoxy, aryloxy and acyloxy radicals together with a halogen group selected from the class consisting of chlorine and bromine and attached directly to the silicon atom at least one organic radical containing more than 10 carbon atoms, more than 80 percent of the hydrolyzable groups being oxy groups and less than 20 percent by weight of the hydrolyzable groups being halogen groups, and moistening the hair with an aqueous composition while arranged in the desired position to cause hair setting.

6. A hair treating composition comprising a nonaqueous composition containing from l-8 percent by weight of a silane having attached to the silicon atom at least two but less than four hydrolyzable groups selected from the class consisting of alkoxy, aryloxy and acyloxy radicals and alkoxy, aryloxy and acyloxy radicals together with a halogen group selected from the class consisting of chlorine and bromine and from 1-3 percent by weight of a polysiloxane fluid formed by the hydrolyzation of a silane having more than 10 carbon atoms in an organic group attached directly to the silicon atom and by the polymerization of the resulting silanol.

'7. A hair treating composition comprising a nonaqueous composition containing from 2-7 percent by weight of a silane having attached to the silicon atom at least two but less than four hydrolyzable groups selected from the class consisting of alkoxy, aryloxy, and acyloxy radicals and alkoxy, aryloxy and acyloxy radicals together with a halogen group selected from the class consisting of chlorine and bromine and having attached directly to the silicon atom organic radicals containing less than 7 carbon atoms and from l-3 percent by weight of a silane having attached to the silicon atom at least two but less than four hydrolyzable groups selected from the class consisting of alkoxy, aryloxy and acyloxy radicals and alkoxy, aryloxy and acyloxy radicals together with a halogen group selected from the class consisting of .10 chlorine and bromine and having attached directly to the silicon atom at least one organic radical containing more than 10 carbon atoms.

8. A hair treating composition comprising a nonaqu'eous composition containing 2-7 percent by weight of a silane having at least two but less than four hydrolyzable oxy radicals and attached directly to the silicon atom an organic radical containing less than 7 carbon atoms and l-3 percent by weight of a silane containing at least two but less than four hydrolyzable oxy groups and attached directly to the silicon atom at least one organic radical containing more than l0'carbon atoms.

9. A hair treating composition comprising a nonaqueous composition containing 27 percent by weight of a silane having at least two but less than four hydrolyzable radicals and having attached directly to the silicon atom organic radicals containing less than 7 carbon atoms and 1-3 percent by weight of a silane having at least two but less than four hydrolyzable groups and attached directly to the silicon atom at least one organic radical containing more than 10 carbon atoms, the hydrolyzable groups being formed of at least 80 percent oxy groups and from l-ZO percent byweight halogen groups.

10. A hair treating composition comprising a nonaqueous composition containing 27 percent by weight of a silane having attached to the silicon atom at least two but less than four hydrolyzable groups selected from the class consisting of alkoxy, aryloxy and acyloxy radicals and alkoxy, aryloxy and acyloxy radicals together with a halogen group selected from the class consisting of chlorine and bromine and attached directly to the silicon atom organic radicals containing less than 7 carbon atoms and l-3 percent by weight of a silane having attached to the silicon atom at least two but less than four hydrolyzable groups selected from the class consisting of alkoxy, aryloxy and acyloxy radicals and alkoxy, aryloxy and acyloxy radicals together with a halogen group selected from the class consisting of chlorine and bromine and attached directly to the silicon atom at least one organic radical containing more than 10 carbon atoms, and less than 1 percent by weight catalyst selected from the group consisting of acids and alkalies soluble in the non-aqueous medium.

11. A hair treating composition comprising a nonaqueous composition containing 27 percent by weight of a silane having attached to the silicon atom at least two but less than four hydrolyzable groups selected from the class consisting of alkoXy, aryloxy and acyloxy radicals and alkoxy, aryloxy and acyloxy radicals together with a halogen group selected from the class consisting of chlorine and bromine and attached directly to the silicon atom organic radicals containing less than 7 carbon atoms and 1-3 percent by weight of a silane having at tached to the silicon atom at least two but less than four hydrolyzable groups selected from the class consisting of alkoxy, aryloxy and acyloxy radicals and alkoxy, aryloXy and acyloxy radicals together with a halogen group selected from the class consisting of chlorine and bromine and attached directly to the silicon atom at least one organic radical containing more than 10 carbon atoms, and 1-3 percent by weight of a polysiloxane fluid formed by the hydrolyzation of a silane having more than 10 carbon atoms in an organic group attached directly to the silicon atom and by the polymerization of the resulting silanol.

12. A hair treating composition comprising a nonaqueous composition containing 2-7 percent by weight of a silane having attached to the silicon atom at least two out less than four hydrolyzable groups selected from the class consisting of alkoxy, aryloxy and acyloxy radicals and alkoxy, aryloxy and acyloxy radicals together with a halogen group selected from the class consisting of chlorine and bromine and attached directly to the silicon atom organic radicals containing less than 7 carbon atoms and 1-3 percent by weight of a silane having attached to the silicon atom at least two but less than four hydrolyzable groups selected from the class consisting of alkoxy, aryloxy and acyloxyradicals and alkoxy, aryloxy and acyloxy radicals together with a halogen group selected from the class consisting of chlorine and bromine and attached directly to the silicon atom at least one organic radical containing more than 10 carbon atoms, and 1-3 percent by weight of a polysiloxane resinous material.

References Cited in the file of this patent UNITED STATES PATENTS 1,055,972 Freeman Mar. 11, 1913 2,327,564 Scherer Aug. 24, 1943 2,390,073 Calva Dec. 4, 1945 2,392,805 Biefeld Jan. 15, 1946 2,415,389 Hunter Feb. 4, 1947 2,439,689 Hyde Apr. 13, 1948 2,530,635 Sowa Nov. 21, 1950 2,643,375 Gant June 23, 1953 FOREIGN PATENTS 594,901 Great Britain Nov. 21, 1947 613,267 Great Britain Nov. 24, 1948 465,257 Canada May 23, 1950 OTHER REFERENCES Lourie: Hair Fixatives, Soap Perfumery and Cosmetics, April 1940, pp. 238-242, esp. at p. 241.

Silicone Notes, Dow Corning Corporation, Midland, Michigan, De Cetex 104, ref. No. 1043, August 1, 1950, 6 pages.

Silicone Notes, Dow Corning Corporation, Midland, Michigan, DC 1107, ref. No. 11071, October 4, 1949, 5 pages.

Silicone Notes, Dow Corning Corporation, Midland, Michigan, De Cetex 104, ref. No. 1042, August 1, 1949, 4 pages.

Alexander et al.: Application of Organosilicon Polymers To Wool. J. Soc. Dyers and Colourists, March 1949, pages 107 to 115.

Rochow: Chemistry of the Silicones. New York, Second Printing, 1947, page 55.

Ephraim: Inorganic Chemistry. Nordeman Publishing Company, New York, 1943, fourth edition, revised, pages 832 to 834 Siloxanes.

Report of Nomenclature Committee A. C. 5., April 1946 On Nomenclature of Silicon Compounds. Reprinted from Chem. and Eng. News, volume 24, pages 1233-6, May 10, 1946.

Minutes of the Amsterdam Meetings, part II; Nomenclature of Organosilicon Compounds as adopted by the Commission on Organic Nomenclature, September 1949 (five pages).

John Wiley,

Claims (1)

1. THE METHOD OF CONDITIONING HAIR ON THE HUMAN HEAD COMRPISING THE STEPS OF WETTING THE HAIR WITH A NONAQUEOUS COMPOSITION CONTAINING A SILANE HAVING ATTACHED TO THE SILICON ATAOM AT LEAST TWO BUT LESS THAN FOUR HYDROLYZABLE GROUPS SELECTED FROM THE CLASS CONSISTING OF ALKOXY, ARYLOXY AND ACYLOXY RADICALS AND ALKOXY, ARYLOXY AND ACYLOXY RADICALS TOGETHER WITH AA HALOGEN GROUP SELECTED FROM THE CLASS CONSISTING OF CHLORINE AND BROMINE AND FROM 1-3 PERCENT BY WEIGHT OF A POLYSILOXANE FLUID AND MOISTENING THE HAIR WITH AN AQEEOUS MEDIUM WHILE ARRAANGED IN THE DESIRED POSITION TO CAUSE HAIR SETTING