MXPA99001429A - Cabe conditioning compositions - Google Patents

Abstract

The present invention relates to hair conditioning or detangling compositions containing from about 0.01% to about 2.0% by weight of a quaternary ammonium compound of the formula: from about 0.01% to about 2.0% by weight of a compound of silicone, wherein R is a substituted or unsubstituted alkyl or alkenyl group having from about 11 to about 35 carbon atoms, X is -0-N-R 5, R 1 is a substituted or unsubstituted alkylene group having from about 2 to about 6 carbon atoms, R2, R3 and R4 are each independently an alkyl or hydroxyalkyl group having from about 1 to about 4 carbon atoms, R5 is H or CH3, and A1 is chloride; bromide; alkyl sulfate containing about 1 to approximately 2 carbon atoms, or mixtures of the same

Description

HAIR CONDITIONING COMPOSITIONS CROSS REFERENCE TO RELATED REQUEST This application claims the benefit of provisional application number of the United States 60/074249 filed on February 10, 1998, which is hereby incorporated by reference in its entirety.

FIELD OF THE INVENTION The present invention relates to compositions that are useful for hair conditioning, especially in the form of a permanent hair conditioner or a hair detangling agent.

BACKGROUND The compositions that can be used to condition the hair are well known. The hair conditioning compositions are designed to leave hair manageable, soft and shiny. Handling ability manifests itself as easy to combine in the dry and wet states, as well as to prevent hair from ruffling "in the dry state." Most hair conditioning compositions apply to hair when wet, usually As a post-treatment after shampoo application, very recently, two-in-one conditioning shampoos have been developed that provide cleansing and conditioning of the hair with a single composition, both post-treatment conditioners and two-in-one shampoos. they are usually rinsed after being left in contact with the hair for a short period, and are therefore known in the art as "rinse" type compositions, although the hair conditioning compositions of the present invention may be used. In rinse products, they are particularly directed to a "permanent" product, that is, one that is applied to hair and either in a wet or dry state, and it is not subsequently rinsed. Said permanent products are typically applied to the hair by means of an atomizer in a form varying from a mist to a liquid vapor. The patent of E.U.A. 4,374,825 discloses hair conditioning compositions comprising from about 1 to about 13% of a liquid, volatile hair conditioning agent selected from hydrocarbons and silicones, from 0.1 to about 8% of a water-soluble nonionic polymeric thickener. and from about 0.05 to about 4% of a cationic agent selected from quaternary ammonium salts or salts of fatty amines. The compositions of the '825 patent are in the form of emulsions. The patent of E.U.A. 4,387,090 describes hair conditioning compositions comprising from 1 to 99% volatile hydrocarbon or silicone and up to 1% of a hydrophobic polymeric thickening agent. The compositions optionally comprise up to about 4% of a conditioning agent selected from quaternary ammonium salts and salts of fatty amines. The patent of E.U.A. 4,711,776 discloses hair cosmetic compositions containing from 0.01 to about 20% of branched quaternary ammonium salts and from 0.1 to 30% oils and fats selected from higher alcohols and fatty acid monoglycerides. The patent of E.U.A. 4,777,037 describes hair conditioning compositions containing from 1 to 4% polydimethylcyclosiloxane and from 0.5 to 5% of a quaternary nitrogen containing conditioning agent having two long chain alkyl groups, each of said alkyl groups having from 12 to 18 atoms of carbon. The preferred compositions are said to contain 0.5 to 10% fatty alcohol and 0.1 to 2% terceary amidoamine. The compositions of this patent are in the form of emulsions. The patent of E.U.A. No. 4,784,844 discloses silicone emulsions containing 100 parts by weight of cyclic siloxane; from 0.7 to 666 parts of selected emulsifier of ethoxylated fatty acids, ethoxylated and non-ethoxylated sorbitan esters, ethoxylated alkylphenols and ethoxylated ethers; and from 5 to 960 parts of water, all parts being parts by weight. The patent of E.U.A. 4No. 859,457 describes hair rinsing compositions comprising 0.05 to 0.5% of cationic surfactant and a second component selected from higher alcohols and monoglycerides, said second component being present in the composition at 3 to 15 times the weight of the cationic surfactant. The patent of E.U.A. No. 4,982,728 is directed to cationic dispersions of fatty alcohol which is said to have application in cosmetic preparations for hair and skin care. The dispersions contain from 10 to 25% by weight of a fatty alcohol and from 0.01 to 1% by weight of a cationic surfactant compound. The patent of E.U.A. 4,902,499 discloses hair conditioning compositions containing from 0.01 to 10% of a rigid silicone polymer and a volatile carrier. In some embodiments, the compositions further comprise from 0.1 to 10% of a lipid carrier material (preferably selected from fatty alcohols, fatty esters and monoglycerides) and from 0.05 to 5% of a cationic surfactant (preferably a fatty quaternary dialkylammonium compound). ). The patent of E.U.A. No. 4,910,013 discloses hair styling compositions comprising branched quaternary alkylammonium compounds and silicone compounds. The patent of E.U.A. No. 4,950,468 discloses a hair treatment composition containing 0.05 to 2.5% of a dimethylsilicon rubber and 0.1 to 5.0% of a mixture of stearyltrimonium chloride and behenyltri onium chloride. The components of the composition are said to be strongly adsorbed to the hair and are not easily desorbed, even with washing.

The patent of E.U.A. No. 4,954,335 discloses a hair conditioning composition containing from 0.1 to 5% of a quaternary ammonium compound (preferably containing two fatty alkyl groups), from 0.1 to 5% of an amidoamine, from 0.5 to 5% of a selected volatile conditioning compound. of silicone and aliphatic hydrocarbon, from 1 to 10% of a nonionic surfactant, preferably a fatty alkylpyrrolidone and from 10 to 30% of a polyhydric alcohol, all in a suitable liquid vehicle. The patent of E.U.A. No. 4,973,476 discloses permanent hair conditioning compositions comprising from 75 to 99.9% volatile silicone and from 0.1 to 10% of at least one functional silicone. The compositions may comprise optional ingredients such as antistatic agents, organic esters and surfactants, among others. The patent of E.U.A. No. 4,976,956 discloses hair treatment compositions comprising at least 0.35% of a water-soluble quaternary ammonium compound, from 0.4 to 15% of an oil-soluble quaternary ammonium compound, dispersible in water, from 0.1 to 5% of an amidoamine neutralized with acid and a suitable liquid vehicle. The compositions may also contain optional ingredients such as organic co-solvents, illustrative members lower alcohols, glycols and polyols. Other optional ingredients include long chain fatty alcohols. The compositions are said to be useful in permanent or rinse products. The patent of E.U.A. No. 4,002,762 discloses hair conditioning compositions comprising from 0.5 to 12% of particular volatile silicone compounds, from 0.5 to 3% of a lipid carrier material such as alcohols or fatty esters, and from 0.2 to 4% of a cationic surfactant. The patent of E.U.A. No. 4,288,484 discloses a pre-shampoo conditioning composition containing from 0.1 to 20% of a particular cationic cellulose, of 0.05 to % of a poly (allyldimethylammonium) polymer and from 0.2 to % behenamidopropyldihydroxypropyldimonium chloride. The patent of E.U.A. No. 4,290,555 discloses a conditioner for hair having an oil phase and an aqueous phase. The oil phase contains a variety of volatile and non-volatile silicone components. The aqueous phase contains olealkonium chloride and PEG-8. The patent of E.U.A. 4,374,421 describes hair treatment compositions containing from 0.1 to 10% of a silicone polymer having at least one alkoxy group containing from 12 to 22 carbon atoms, said polymer having a melting point of not less than 30 °. C; 0.1 to 20% of a cationic surfactant; 0.1 to 30% of an alcohol having from 12 to 26 carbon atoms; 0.1 to 90% of an organic alcohol compatible with water; and water. WO 97/07774 describes a hair treatment composition particularly useful as a rinse product containing from 0. 6 to about 10% of a fatty alcohol, 0.01 to 15% of a silicone conditioning agent and from 0.1 to 5. % of an onoalkyltrimethylammonium salt. The silicone conditioning agent is preferably non-volatile, and the ammonium salt is preferably behenyltrimethylammonium chloride. Although many of the references above describe the combination of silicones and quaternary ammonium salts, we do not know of any reference describing hair care compositions incorporating a silicone compound together with a fatty quaternary ammonium compound in which the fatty group is an acyl group, derived for example from an amide or an ester.

There are many important requirements for a permanent conditioning composition. First, the composition must impart the desired conditioning benefits of handling ability, smoothness and shine. Second, the product must be physically and chemically stable. Third, the composition should be gentle and non-irritating to the skin and eyes. This property is especially important when using the composition in children. Fourth, the product should leave a minimum residue in the hair. Finally, the composition must have physical properties such as viscosity, which allow its application by means of an atomizer. Accordingly, an object of the present invention is a conditioning composition that provides the required benefits of handling ability, smoothness and gloss. Another object of the invention is to provide a composition that provides the conditioning benefits required and that is physically and chemically stable. Another object of the invention is to provide a composition that provides the required conditioning benefits and that is mild and non-irritating to the skin and eyes.

Another object of the invention is to provide a composition that provides the conditioning benefits required and that can be applied and left on the hair without leaving an appreciable residue therein. Another object of the invention is to provide a composition that provides the conditioning benefits required and that can be applied to hair in a variety of physical forms, including a spray.

BRIEF DESCRIPTION OF THE INVENTION The present invention relates to a hair conditioning composition comprising, based on the total weight of the composition: A) from about 0.01% to about 2.0% of a quaternary ammonium compound of the formula B) from about 0.01% to about 2.0% of a silicone compound in which R is a substituted or unsubstituted alkyl or alkenyl group having from about 11 to about 35 carbon atoms, X is -0- or N -R5, Ri is a substituted or unsubstituted alkylene group having from about 2 to about 6 carbon atoms, R2, R3 and R4 are each independently an alkyl or hydroxyalkyl group having from about 1 to about 4 carbon atoms; carbon, R5 is H or CH3, and Ai is chloride; bromide; alkyl sulfate containing from about 1 to about 2 carbon atoms; or mixtures thereof. In a preferred embodiment, the invention relates to a conditioning composition comprising: A) a first quaternary ammonium compound of the formula B) a second quaternary ammonium compound of the formula C) based on the total weight of the composition, from about 0.01 to about 2.0 percent of a silicone compound in which R is a substituted or unsubstituted alkyl or alkenyl group having from about 11 to about 35 atoms of carbon, X is -0- or N-R5, Ri is a substituted or unsubstituted alkylene group having from about 2 to about 6 carbon atoms, R2 / R3 and R are each independently an alkyl or hydroxyalkyl group has from about 1 to about 4 carbon atoms, R5 is H or CH3, R6 is an alkyl or alkenyl group having from about 12 to about 36 carbon atoms, R7 is an alkyl or alkenyl group having from about 1 to about 36 carbon atoms or a benzyl group, Rg and R9 are each independently an alkyl group having from about 1 to about 4 carbon atoms or a benzyl group, A and A2 are each independently chloro or; bromide; alkyl sulfate containing from about 1 to about 2 carbon atoms; or mixtures thereof, and wherein the first and second quaternary ammonium compounds together comprise between about 0. 01% to about 2.0% by weight of said composition. Another preferred embodiment of the invention relates to a hair conditioning composition comprising: A) a first quaternary ammonium compound of the formula B) a second quaternary ammonium compound of the formula C) based on the total weight of the composition, from about 0.01 to about 2.0 percent of a silicone compound in which R is an alkyl or alkenyl group having from about 17 to about 21 carbon atoms, X is - 0 - or NH, Ri is a substituted or unsubstituted alkylene group having from about 2 to about 6 carbon atoms, R2, R3 and R4 are each independently an alkyl or hydroxyalkyl group having from about 1 to about 4 carbon atoms, Re is an alkyl or alkenyl group having from about 18 to about 22 carbon atoms, R7, R8 and R9 are each independently an alkyl group having from about 1 to about 4 carbon atoms or a benzyl group, i and A2 are each independently chloride; bromide; alkyl sulfate containing from about 1 to about 2 carbon atoms; or mixtures thereof, and wherein the first and second quaternary ammonium compounds together comprise between about 0.01% to about 2.0% by weight of said composition. Another preferred embodiment of the invention relates to a conditioning composition comprising, based on the total weight of the composition: A) from about 0.05% to about 1.0 percent of a first quaternary ammonium compound B) from about 0.05% to about 1.0 percent of a second quaternary ammonium compound C) from about 0.05% to about 1.0 percent of a volatile silicone compound having from about 4 to about 6 silicon atoms, wherein R is an alkyl group having about 21 carbon atoms X is NH, Ri is a substituted or unsubstituted alkylene group having from about 2 to about 6 carbon atoms, R2, R3 and R4 are each independently an alkyl or hydroxyalkyl group having about 1 carbon atom. at about 4 carbon atoms, R6 is an alkyl group having approximately 22 carbon atoms, R7, Re and R9 are each independently CH3, i and A2 are each independently chloride; bromide; alkyl sulfate containing from about 1 to about 2 carbon atoms; or mixtures thereof, DETAILED DESCRIPTION OF THE INVENTION In a first embodiment, the invention relates to hair conditioning compositions containing a quaternary ammonium compound of the formula I wherein R is a substituted or unsubstituted alkyl or alkenyl group having from about 11 to about 35 carbon atoms, X is -0- or N-R5, Ri is an alkylene group having from about 2 to about 6 carbon atoms, said alkylene group being unsubstituted or substituted, that is, with a functional group such as a hydroxyl group; R2, R3 and R4 are each independently an alkyl or hydroxyalkyl group having from about 1 to about 4 carbon atoms. The substituted hydroxyalkyl groups being hydroxyethyl, hydroxypropyl or dihydroxypropyl; R5 is H or CH3, and Ai is chloride; bromide; alkyl sulfate containing from about 1 to about 2 carbon atoms; or mixtures thereof.

It is well known in the art that long chain functional hydrocarbons are materials that occur in nature as mixtures of variable chain length. Accordingly, in the case of refined materials, R can represent a group having a single chain length. Alternatively, in the case of less refined materials, R may represent a material having a mixture of different chain lengths within the wider prescribed range. In a preferred embodiment, the quaternary ammonium compound I has the structure shown above wherein R is an alkyl group having from about 17 to 21 carbon atoms, preferably from about 19 carbon atoms to about 21 carbon atoms, or mixtures thereof; X is a group N-R5; R5 is H and the other structural elements are as defined above. The composition of the invention comprises, based on the total weight of the composition, from about 0.01% to about 2.0%, preferably from about 0.05% to about 1.0%, and most preferably from about 0.1 to about 0.5% by weight. weight of the quaternary ammonium compound. Illustrative materials useful as the quaternary ammonium compound in the compositions of the invention include compounds having the following formulas II to V: IV V The compound of the formula II in which i is ethosulfate is available as Chercoquat BAS "from Scher Chemicals, Inc. of Clifton, New Jersey The compound of the formula II in which i is chloride, is available as" Lexquat AMG " "BEO" by Inolex Chemical Co. of Philadelphia, PA The compound of formula IV in which Ai is chloride is available as "Akypoquat 131" from Chemische Fabrik Chem-Y of Emmerich, Germany. wherein i is chloride, is available as "Incroquat Behenyl HE" from Croda, Inc. of Parsippany, New Jersey The latter material, which is a mixture of 50% of the compound of formula V in hexylene glycol, is a preferred source of the quaternary ammonium compound useful in the compositions of the invention The compositions of the invention further comprise, based on the total weight of the composition, from about 0.01% to about 2.0%, and preferably from about 0.05% to about 1.0% of an organic silicone compound. Preferably, suitable silicone compounds are in the form of a fluid or a gum. Silicone compounds useful in the compositions of the invention include, but are not limited to dimethicones, which are a mixture of the fully methylated linear siloxane polymers blocked at the ends with trimethylsiloxy units.; cyclomethicones, which are cyclic dimethylpolysiloxane compounds having from about 3 to about 6 silicon atoms; and mixtures thereof.

Preferably, the organic silicone compounds useful in the compositions of the invention are volatile, ie they have a boiling point below about 250 ° C. Cyclomethicones having between about 4 and about 6 silicon atoms are especially useful in this regard. An exemplary material useful in the compositions of the invention is "Dow Corning 344 Fluid," available from Dow Corning of Midland, Michigan. This material consists of approximately 77% by weight of octamethylcyclotetrasiloxane and approximately 22% by weight of decamethylpentasiloxane. In another embodiment, the invention relates to hair conditioning compositions comprising a mixture of at least two cationically charged quaternary ammonium compounds. The first of these quaternary ammonium compounds is of the formula I as described hereinabove. The second quaternary ammonium compound has the structure: VI where: Re is an alkyl or alkenyl group having from about 12 to about 36 carbon atoms, R7 is an alkyl or alkenyl group having from about 1 to about 36 carbon atoms, or a benzyl group, Rs and Rg are each independently, an alkyl group having from about 1 to about 4 carbon atoms or a benzyl group , A2 is chlorine, bromine, alkyl sulfate containing from about 1 to about 2 carbon atoms; or mixtures thereof. As was the case with the group R in the compound of formula I, R6 and R- can represent groups with an individual chain length or a material containing a mixture of different chain lengths. The second quaternary amino compound may contain one or two fatty chains, but materials containing a fatty alkyl chain are preferred. In a preferred embodiment, the substituents on the nitrogen atom of the second quaternary ammonium compound are as follows: Re is an alkyl or alkenyl group having from about 18 to about 22 carbon atoms, preferably from about 20 to about 22 carbon atoms, and preferably about 22 carbon atoms, and R7, Re, and R9 are each independently, an alkyl group having from about 1 to about 4 carbon atoms, or a benzyl group, and preferably a group methyl. Exemplary materials useful as the second quaternary ammonium compound in the compositions of the invention include, but are not limited to, behenalkonium chloride, available from Hoechst Celanese Company of Charlotte, North Carolina, under the trademark "Genamin KDB", dibehenildimony, available from Witco Corp. of Dublin Ohio as "Kemamine Q-2802C", dibehenildimony methosulphate available from Croda, Inc. of Parsippany, New Jersey, under the trademark "Incroquat DBM-90", dibenzylchloride / diarachyldildimonium, available of Witco as "Kemamine Q-1902C", behentrimonium chloride available from Hoechst Celanese as "Genamin KDM", behentrimonium methosulfate available from Croda, Inc. under the brand name Incroc at Behenyl TMS ", and mixtures thereof. is a mixture containing 25% behentrimonium methosulfate and 75% cetearyl alcohol, and is a particularly preferred raw material for the second quaternary ammonium compound in the composition it is of the invention. When the two quaternary ammonium compounds described above, ie the compounds of formula I and of formula VI, are present in the compositions of the invention, they comprise together, based on the total weight of the composition, between about 0. 01% and about 2.0%, preferably between about 0.05% and about 1.0%, and between about 0.1% and about 0.5% of the composition is very preferred. The weight ratio between the first quaternary ammonium compound and the second quaternary ammonium compound, is preferably in the range of about 4: 1 to about 1: 4, and preferably in the range of about 2: 1 to about 1: 2. The compositions of the invention may also comprise additional components such as glycols or polyols, surfactants and fatty alcohols. Exemplary glycols include, but are not limited to, propylene glycol, butylene glycol, hexylene glycol, and mixtures thereof. An exemplary polyol useful in the compositions is glycerin.

The compositions of the invention may be in the form of a shampoo conditioner, a rinse conditioner, a permanent conditioner or a hair detangling agent. Preferably, the compositions are in the form of a permanent conditioner. When in the form of a shampoo, the compositions of the invention normally contain surfactants in a concentration required to clean the hair, totaling in the range from about 5% to about 20% by weight of the composition. The surfactants in the shampoo compositions may include anionic, nonionic or amphoteric surfactants, or mixtures of these surfactants. When in the form of a permanent conditioner, the compositions of the invention preferably comprise a relatively smaller amount of a nonionic surfactant, usually in the range from about 0.01% to about 1.0% by weight of the composition. Exemplary classes of nonionic surfactants useful in permanent conditioners containing the compositions of the invention, include but are not limited to alkoxylated alcohols and alkoxylated polyol esters. Preferably, the nonionic surfactants are ethoxylated alcohols, ethoxylated polyol esters, or mixtures thereof. In this regard, useful exemplary materials include ethoxylated lanolin and ethoxylated sorbitan esters. An exemplary ethoxylated lanolin, useful in the compositions of the invention is, PEG-60 lanolin, available as "Solan 50" from Croda, Inc. An exemplary ethoxylated sorbitan ester, useful in the compositions of the invention, is polyoxyethylene monolaurate ( 20) sorbitan, available as "Tween 20" from ICI Surfactans of Wilmington, Delaware. When in the form of a permanent conditioner, the compositions may also comprise, based on the total weight of the composition, from about 0.01% to about 1.0% of a fatty alcohol having from about 12 to about 36 carbon atoms. Exemplary fatty alcohols include, but are not limited to, lauryl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol and mixtures thereof. When they are in the form of a product other than shampoo, that is, permanent conditioner or detangling agent, the composition is preferably substantially free of any anionic surfactant. By "substantially free", it is understood that the composition does not contain more than 0.5% by weight, and preferably not more than 0.1% by weight of anionic surfactants. The compositions may further comprise optional functional ingredients such as pH regulators, preservatives and fragrance. For the maximum convenience of the consumer, preferably the package containing the composition of the invention is a dispensing package such as a spray dispenser or a foam dispenser. When the composition of the invention is in the form of a permanent conditioner or a hair detangler, it is preferably contained in a spray dispenser package. Said packages contain a piston pump by means of which the composition is dispensed in the form of a mist, droplets or a stream of liquid. As such, the permanent conditioners or hair detanders comprising the compositions of the invention, should have a relatively low viscosity to allow the compositions to be easily dispersed by means of said pump dispensers.

The compositions of the invention are especially useful in hair detangling products, where it facilitates the disentangling of entangled hair, reducing the force required to comb the entangled hair as discussed hereinabove. The compositions can be used with wet or dry hair. If the hair is wet, it is preferable to compress the hair to remove excess water, and that the compositions of the invention are applied uniformly to the hair, as for example from a spray dispenser. The composition can then be handled on the hair, and then the hair can be combed and brushed. Alternatively, for use on dry hair, the compositions should be applied to the hair until it becomes damp and then combs or brushes the hair. Several examples are set forth below to further illustrate the nature of the invention and the manner of carrying it out. However, the invention should not be considered as limited to the details thereof.

EXAMPLE 1 A hair detangler composition having the formula shown in Table 1 was prepared as follows: TABLE 1 Formulation of example 1 The required amounts of Incroquat TMS, Incroquat HE, Solan 50 and fluid DC344, were charged to a heated mixing vessel, equipped with a high speed stirrer / impeller. The vessel was heated to a temperature of about 75 ° to 80 ° C to melt the ingredients, and the contents were then mixed at high speed for about 5 minutes. The water was heated in a separate vessel at about the same temperature, i.e., 75 to 80 ° C, then about 10% to about 15% of the total water charge was added to the pre-melt components in the vessel with stirring. mixed, keeping the container at 75-80 ° C. Mixing and heating is continued for approximately another 10 to 15 minutes until the pre-dissolved components are completely dispersed in the aqueous phase. The rest of the heated water was added to the mixing vessel and stirring was continued for another 10 minutes. The contents of the mixing vessel were allowed to cool to about 45 ° C, and then the preservative Kathon and the fragrance were added. The contents were allowed to cool further to room temperature. Preferably, the composition has a pH of about 4 to about 5, and preferably between about 4.2 and about 4.4. If necessary, the pH of the composition can be adjusted with an acid such as citric acid, to bring the pH of the composition to the desired value.

EXAMPLE 2 A hair detangler composition having the formula shown in Table 2 was prepared following the procedure of Example 1, except that Solan 50 was replaced with Tween 20.

TABLE 2 Formulation of example 2 Product Stability The stability of the compositions of Examples 1 and 2 was determined by incubating samples of the formulations at various temperatures from room temperature to about 50 ° C, and by measuring the pH and optical appearance of the samples. The samples, which were uniform opaque dispersions, remained unchanged in appearance upon standing for up to 6 weeks at temperatures from room temperature to 50 ° C. In the same way, the pH of the samples remained stable during this period. Also, the samples were subjected to freeze-thaw stability. Each freeze-thaw cycle included cooling the samples from -20 to -10 ° C, keeping them at this temperature for approximately 24 to 36 hours, returning them and keeping them at room temperature for an additional 24 to 36 hours. There was no discernible change in the appearance of the samples when subjected to 5 of these freeze-thaw cycles.

Detangling action The detangling action of the products of Example 1 and 2 was evaluated on test consumer panelists. Each panelist evaluated the composition of one of the examples against a commercially available control product, "Johnson 's Kids No More Tangles" Detangling Spray, marketed by Johnson & Johnson Consumer Products, Inc. The compositions of each example were evaluated by 70 panelists in sequential nomadic (blind) trials. Each panelist was given a spray dispenser package containing the first product (any of the compositions of Examples 1 or 2, or the control), and instructed to apply the product to wet hair after washing it. Some of the panelists were also instructed to use the product on dry hair. After a week, the panelists were instructed not to use any detangling for 3 days. The second sample was given and they were instructed to apply it for a second week. The panelists were instructed to fill out a questionnaire after each use. The following test results were determined: TABLE 3 Detangling action TABLE 4 Detangling action The panelists found that the compositions improve the manageability of the hair when applied under dry or wet conditions. The detangling efficiency of the compositions of the invention was also measured in the laboratory, in the following manner: It was measured in detangling in braids of 2.5 cm per cm long, composed of double-bleached blonde hair that was purchased from International Hair Importers and Products, Inc. of New York City. The braids were washed applying 1 ml of surfactant "Tergitol 15-S-9" (Union Carbide Corp.) to the braids, soaping for 2 minutes and rinsing for an additional 3 minutes. This washing procedure was repeated a total of 3 times the combed braid to completely remove the tangles. The tangles were again introduced into the braids by soaking the braids in a water flask and removing the braids a total of 3 times. The braid was fastened on a Dia-Stron 160 miniature series voltage tester (Dia-Stron Ltd., Broomal, Pennsylvania). A plastic comb with teeth separated at a distance of 0.31 cm was also attached to the apparatus. The tension tester measures the load (in grams of force) required to pass the comb through the braid as a function of the distance the apparatus was activated and the force of the comb against the distance was recorded. The braid became entangled again by soaking in water, and the detangling force was measured a total of 3 times. The average value of the peak force of 3 consistent readings represents the baseline value to untangle the braid. Again, the braid became entangled again, and the effectiveness of a detangling composition was determined by sprinkling 0.3 g of the composition on the braid, holding the braid in the tension tester, and once again measuring the peak force. The treated braid became entangled once again, and the force was again measured to move the comb through the braid. An average of three of these determinations is taken as the force to untangle the treated braid. The percentage reduction in combing force was calculated as follows: Strength of baseline - strength treated % reduction of comb force = X 100 Strength of the baseline Figure 1 shows a graph illustrating the strength of the comb for a braid, which evaluates the effectiveness of the composition of Example 2, in which the grams of force on the Y axis are plotted against the distance on the X axis. Table 5 shows the reduction percentage of the comb force for the compositions of examples 1 and 2, together with several other compositions.

TABLE 5 Hairstyle reduction data The data indicates the excellent unraveling ability of the compositions of the invention. The data also suggest that the compositions of Examples 1 and 2 which incorporate the quaternary ammonium compounds behentrimonium methosulfate and behenamidopropylhydroxyethyldimonium chloride having the longer C22 groups, are more effective in untangling the hair than other compositions comprising species having shorter hydrocarbon chains, ie, stearoalkonium chloride or dimethyldialkyl (Cis) ammonium chloride.

Eye irritation The compositions of this invention also exhibited very low irritation to eyes and skin. Irritation has been evaluated according to the Invittox No. 86 protocol of the "Trans-epithelial Permeability (TEP) Assay (transepithelial permeability test)." According to the PET test, the ocular irritation potential of the patient can be evaluated. A product determining its effect on the permeability of a cell layer, determined by the leakage of fluorescein through the layer.In accordance with this method in vi tro, monolayers of Madin-Darby canine kidney cells (MDCK) are developed to confluence on microporous inserts in a 24 well plate containing test medium or pH regulator in the lower wells The irritation potential of a product is evaluated by measuring the damage to the barrier permeability in the cell monolayer after exposure 15 minutes to dilutions of the product The damage to the barrier is determined by the amount of sodium fluorescein that has leaked through the lower well after 3 hours. 0 minutes, determined by spectrophotometry. Fluorescein leakage is plotted against the concentration of test material to determine EC5o (the concentration of test material that causes 50% maximum dye leakage, that is, 50% damage to the permeability of the barrier). The test procedure is indicated in Invittox Protocol No. 86 (May 1994), the description of which is incorporated herein by reference. The exposure of a layer of MDCK cells developed on a microporous membrane to the test sample is a model for the first event that occurs when an irritant makes contact with the eye. In vivo, the outermost layers of the corneal epithelium form a selectively permeable barrier due to the presence of tight junctions between the cells. Upon exposure to an irritant, the tight junctions separate, removing the permeability of the barrier. Fluid is assimilated in the underlying layers of the epithelium and stroma, causing separation of the collagen lamellae, resulting in opacity. The PET test measures the effect of an irritant on the separation of tight junctions between cells in a layer of MDCK cells grown on an icroporous insert. The damage is evaluated spectrophotometrically by measuring the amount of marker dye (sodium fluorescein) that leaks through the cell layer and the microporous membrane into the lower well. In general, a pass rating is reflected in an EC50 of 2.2% or higher. The undiluted composition of Example 1 prepared in accordance with the present invention showed no leak, and therefore has a passing TEP rating. This data demonstrates that the compositions of the present invention can be expected to be exceptionally gentle for the eyes.

EXAMPLES 3-11 The formulations of Examples 3-11 shown in Table 6 were prepared, using the procedure of Example 1.

TABLE 6

Claims (1)

NOVELTY OF THE INVENTION CLAIMS 1. - A composition comprising, based on the weight of the composition: A) from about 0.01% to about 2.0% of a quaternary ammonium compound of the formula B) from about 0.01% to about 2.0% of a silicone compound in which R is a substituted or unsubstituted alkyl or alkenyl group having from about 11 to about 35 carbon atoms, X is - 0 - or N -R5, Ri is a substituted or unsubstituted alkylene group having from about 2 to about 6 carbon atoms, R2, R3 and R are each independently an alkyl or hydroxyalkyl group having from about 1 to about 4 carbon atoms; carbon, R5 is H or CH3, and i is chloride; bromide; alkyl sulfate containing from about 1 to about 2 carbon atoms; or mixtures thereof. 2. The composition of claim 1, comprising from about 0.1% to about 1.0 weight percent of said quaternary ammonium compound 3. The composition of claim 1, further characterized in that R is an alkyl group having from about 19 to about 21 carbon atoms or mixtures thereof, X is a group N-R5 and R5 is H. 4. The composition of claim 1, further characterized in that said quaternary ammonium compound is selected from: B. D. and E. mixtures thereof. 5. The composition of claim 1, further characterized in that said quaternary ammonium compound comprises 6. - The composition of claim 1, comprising from about 0.05 to about 1.0 percent of a silicone compound. 7. The composition of claim 1, further characterized in that said silicone compound is a volatile polydi ethylsiloxane having from about 4 to about 6 silicon atoms. 8. The composition of claim 1, further characterized in that it comprises a glycol or polyol having from about 3 to about 6 carbon atoms. 9. - The composition of claim 1, further characterized in that it comprises from about 0.01 to about 1.0% by weight of a nonionic surfactant. 10. The composition of claim 9, further characterized in that said nonionic surfactant is selected from alkoxylated alcohols and alkoxylated polyol esters. 11. The composition of claim 10, further characterized in that said nonionic surfactant is selected from ethoxylated lanolin, ethoxylated sorbitan esters and mixtures thereof. 12. The composition of claim 1, further characterized in that it comprises from about 0.01 to about 1.0% by weight of at least one fatty alcohol having from about 12 to about 36 carbon atoms. 13. The composition of claim 1, in the form of a shampoo conditioner, a rinse conditioner, a permanent conditioner or a hair detangling agent. 14. The composition of claim 13, in the form of a permanent conditioner or a hair detangler. 15. The composition of claim 1, which has a sufficient viscosity and rheology to allow said composition to be supplied by means of an atomizer. 16. An article of manufacture containing the composition of claim 1. 17. The article of manufacture of claim 16, which contains the composition of claim 1 contained within a spray container or a foam assortment container. 18. A composition containing: A) a first quaternary ammonium compound of the formula B) a second quaternary ammonium compound of the formula C) from about 0.01 to about 2.0 percent, based on the total weight of the composition, of a silicone compound in which R is a substituted or unsubstituted alkyl or alkenyl group having from about 11 to about 35 carbon atoms, X is -0- or N-R5, Ri is a substituted or unsubstituted alkylene group having from about 2 to about 6 carbon atoms, R2, R3 and R4 are each independently an alkyl or hydroxyalkyl group having about 1 to about 4 carbon atoms, R5 is H or CH3, R6 is an alkyl or alkenyl group having from about 12 to about 36 carbon atoms, R7 is an alkyl or alkenyl group having from about 1 to about 36 carbon atoms or a benzyl group, Rs and R9 are each independently an alkyl group having from about 1 to about 4 carbon atoms or a benzyl group, Ai and A2 are each independently chloride; bromide; alkyl sulfate containing from about 1 to about 2 carbon atoms; or mixtures thereof, and wherein the first quaternary ammonium compound and the second quaternary ammonium compound together comprise between about 0.01% to about 2.0% by weight of said composition. 19. - The composition of claim 18, further characterized in that Re is an alkyl group having approximately 22 carbon atoms and R ?, Rs and R9 are each CH3. 20. The composition of claim 18, further characterized in that the weight ratio of the first quaternary ammonium compound to the second quaternary ammonium compound is from about 4: 1 to about 1: 4. 21. The composition of claim 18, further characterized in that the weight ratio of the first quaternary ammonium compound to the second quaternary ammonium compound is from about 2: 1 to about 1: 2. 22. A composition containing: A) a first quaternary ammonium compound of the formula B) a second quaternary ammonium compound of the formula C) based on the total weight of the composition, from about 0.01 to about 2.0 percent of a volatile silicone compound wherein: R is an alkyl or alkenyl group having from about 17 to about 21 carbon atoms , X is -0- or NH, Ri is a substituted or unsubstituted alkylene group having from about 2 to about 6 carbon atoms, R2 / R3 and R4 are each independently an alkyl or hydroxyalkyl group having from about 1 to about 4 carbon atoms, R6 is an alkyl or alkenyl group having from about 18 to about 22 carbon atoms, R7, Rs and R9 are each independently an alkyl group having from about 1 to about 4 atoms of carbon or a benzyl group, Ai and A2 are each independently chloride; bromide; alkyl sulfate containing from about 1 to about 2 carbon atoms; or mixtures thereof, and wherein the first and second quaternary ammonium compounds together comprise between about 0.01% to about 2.0% by weight of said composition. 23. - A hair conditioning composition comprising: A) from about 0.05% to about

1. 0 percent of a first quaternary ammonium compound B) from about 0.05% to about 1.0 percent of a second quaternary ammonium compound C) from about 0.05% to about 1.0 percent of a volatile silicone compound having from about 4 to about 6 silicon atoms, wherein R is an alkyl group having about 21 carbon atoms X is NH, Ri is a substituted or unsubstituted alkylene group having from about 2 to about 6 carbon atoms, R 2, R 3 and R 4 are each independently an alkyl or hydroxyalkyl group having from about 1 to about 4 carbon atoms, R 6 is an alkyl group having approximately 22 carbon atoms, R7, Rs and Rg are each independently CH3, Ai and A2 are each independently chloride; bromide; alkyl sulfate containing from about 1 to about 2 carbon atoms; or mixtures thereof. 24. A method of conditioning or to untangle the hair that consists in applying an effective amount to condition or disentangle the hair of the composition of claim 1 to the hair.