WO2000000169A1

WO2000000169A1 - Method of conditioning hair

Info

Publication number: WO2000000169A1
Application number: PCT/US1998/013923
Authority: WO
Inventors: Timothy Woodrow Coffindaffer
Original assignee: The Procter & Gamble Company
Priority date: 1998-06-29
Filing date: 1998-06-29
Publication date: 2000-01-06
Also published as: BR9911640A; CN1307469A; JP2002522356A; WO2000000172A1; EP1091728A1; AU8383198A; AU4843999A

Abstract

Method of conditioning the hair comprising applying to the hair an effective amount of a conditioner composition wherein the conditioner composition comprises: (a) a mono-ol or diol solvent having a ClogP of from about 0.15 to about 0.64; and (b) quaternary ammonium cationic conditioning agent having the formula (1): [(R)4-m-N?(+)-[(CH¿2)n-Y-R1]m] X(-) wherein each R substituent is a short chain C¿1?-C6 alkyl or hydroxyalkyl group, benzyl, or mixtures thereof; each m is 2 or 3; each n is from 1 to about 4; each Y is -O-(O)C-, or -C(O)-O-; each R?1¿ is a hydrocarbyl, or substituted hydrocarbyl group, the sum of carbons in each R1, plus one when Y is -O-(O)C-, being C¿12?-C22; the average Iodine Value of the parent fatty acid of the R?1¿ group being from about 60 to about 140; and wherein the counterion, X- is any softener-compatible anion; the level of conditioning agent containing polyunsaturated alkylene groups being at least about 3 % by weight of the total conditioning agent present and wherein the aqueous dispersion comprises a mixture of monoester and diester. The method herein provides excellent hair detangling, improved wet clean feel on rinsing and post rinsing, and minimizes volume loss.

Description

Method of Conditioning Hair

Technical Field

The present invention relates to a method for conditioning the hair.

Background of the Invention

Scalp hair becomes soiled due to its contact with the surrounding environment and from sebum secreted from the hair follicles. The build-up of sebum and environmental soiling can cause the hair to have a dirty or greasy feel, and an unattractive appearance. In order to ameliorate these effects, it is necessary to shampoo the hair regularly.

Shampooing the hair removes excess sebum and other environmental soiling. However, the shampooing process has disadvantages in that the hair is left in a wet, tangled and generally unmanageable state. Shampooing can also result in the hair becoming dry and frizzy, and a loss of lustre, due to removal of natural oils or other hair moisturizing materials. After shampooing, the hair can also suffer from a loss of "softness" perceived by the user upon drying. The hair can also suffer from increased levels of static upon drying after shampooing. This can interfere with combing and can result in fly-away hair.

A variety of approaches have been developed to condition the hair. These range from post-shampooing hair rinses, to leave-on hair conditioners, to the inclusion of hair conditioning components in shampoos. There are several advantages for providing hair conditioning components such as silicones in shampoos. First of all many consumers prefer the ease and convenience of a shampoo which includes conditioners. An additional advantage of conditioning shampoo compositions is that such compositions provide a good in-use wet hair feel compared to shampoos which do not contain conditioning ingredients. A substantial proportion of consumers however prefer the more conventional conditioner formulations which are applied to the hair as a separate step from shampooing, usually subsequent to shampooing. These hair conditioners typically are formulated as a thickened product, such as a gel or cream, for ease of dispensing and application to the hair. Consumers who have fine or straight hair may ideally prefer conditioners which provide increased hair volume at the same time as providing conditioning/detangling benefits. Many conventional conditioning compositions based on fatty alcohols and many conditioning shampoos relying upon conditioning ingredients such as silicones, although effective at providing a detangling benefit, cause a decrease in hair volume. It would therefore be desirable to provide a method of conditioning the hair which minimized decrease in hair volume following conditioning.

It would be even more desirable to provide a method of conditioning the hair which provides good in-use wet hair feel, a wet clean feel on rinsing and post rinsing, dry clean feel, good detangling and which minimizes volume loss typically experienced with conventional conditioners.

It has now surprisingly been found that a method of conditioning the hair wherein a composition comprising a solvent and a quaternary ammonium conditioning agent is applied to the hair a good clean feel on rinsing and post rinsing, good dry clean feel, together with excellent detangling and minimized hair volume loss typically experienced with conventional conditioning compositions.

Summary of the Invention

According to the present invention there is provided a method of conditioning the hair comprising applying to the hair an effective amount of a conditioner composition wherein the conditioner composition comprises:

(a) a mono-ol or diol solvent having a ClogP of from about 0.15 to about

0.64; and (b) quaternary ammonium cationic conditioning agent having the formula (I):

(R)4-m - N(⁺) -[(CH₂)_n-Y- ¹]m X (-)

(1)

wherein each R substituent is a short chain Cj-Cg alkyl or hydroxyalkyl group, benzyl, or mixtures thereof; each m is 2 or 3; each n is from 1 to about 4; each Y is -O-(O)C-, or -C(O)-O-; each R! is a hydrocarbyl, or substituted hydrocarbyl, group, the sum of carbons in each R , plus one when Y is -O-(O)C-, being C12- C22; the average Iodine Value of the parent fatty acid of the Rl group being from about 60 to about 140; and wherein the counterion, X" is any softener-compatible anion; the level of conditioning agent containing polyunsaturated alkylene groups being at least about 3% by weight of the total conditioning agent present and wherein the aqueous dispersion comprises a mixture of monoester and diester.

The method of the present invention provides excellent in-use wet feel, excellent clean feel during rinsing and post-rinsing, good dry clean feel and excellent detangling, in addition to minimizing volume loss versus methods using conventional conditioning compositions.

The concentrations and ratios herein are by weight of composition, unless otherwise specified. Surfactant chain lengths are also on a weight average chain length basis, unless otherwise specified.

Detailed Description of the Invention

The method of the present invention comprises applying to the hair an effective amount of a conditioner composition wherein the conditioner composition comprises a mono-ol or diol solvent having a ClogP of from about 0.15 to about 0.64 and a quaternary ammonium cationic conditioning agent.

Principal Solvent System

The conditioning compositions of the present invention also comprise a principal solvent system in addition to water. This is particularly important for formulating liquid, clear hair conditioning compositions. When employed, the principal solvent preferably comprises less than about 40%, preferably from about 5% to about 35%, more preferably from about 5% to about 20%, and even more preferably from about 5% to about 15%, by weight of the composition. The principal solvent is selected to minimize solvent odor impact in the composition and to provide a low viscosity to the final composition. For example, isopropyl alcohol is not very effective and has a strong odor. n-Propyl alcohol is more effective, but also has a distinct odor. Several butyl alcohols also have odors but can be used for effective clarity/stability, especially when used as part of a principal solvent system to minimize their odor. The alcohols are also selected for optimum low temperature stability, that is they are able to form compositions that are liquid with acceptable low viscosities and translucent, preferably clear, down to about 40°F (about 4.4°C) and are able to recover after storage down to about 20°F (about 6.7°C).

Suitable solvents for use herein can be selected based upon their octanol/water partition coefficient (P). Octanol/water partition coefficient of a principal solvent is the ratio between its equilibrium concentration in octanol and in water. The partition coefficients of the principal solvent ingredients of this invention are conveniently given in the form of their logarithm to the base 10, logP.

The logP of many ingredients has been reported; for example, the Pomona92 database, available from Daylight Chemical Information Systems, Inc. (Daylight CIS), Irvine, California, contains many, along with citations to the original literature. However, the logP values are most conveniently calculated by the "CLOGP" program, also available from Daylight CIS. This program also lists experimental logP values when they are available in the Pomona92 database. The "calculated logP" (ClogP) is determined by the fragment approach of Hansch and Leo (cf, A. Leo, in Comprehensive Medicinal Chemistry, Vol. 4, C. Hansch, P. G. Sammens, J. B. Taylor and C. A. Ramsden, Eds., p. 295, Pergamon Press, 1990, incorporated herein by reference). The fragment approach is based on the chemical structure of each ingredient, and takes into account the numbers and types of atoms, the atom connectivity, and chemical bonding. These ClogP values, which are the most reliable and widely used estimates for this physicochemical property, are preferably used instead of the experimental logP values in the selection of the principal solvent ingredients which are useful in the present invention. Other methods that can be used to compute ClogP include, e.g., Crippen's fragmentation method as disclosed in J. Chem. Inf. Comput. Sci., 27, 21 (1987); Viswanadhan's fragmentation method as disclose in J. Chem. Inf. Comput. Sci., 29, 163 (1989); and Broto's method as disclosed in Eur. J. Med. Chem. - Chim. Theor., 19, 71 (1984). The principal solvents herein are selected from those having a ClogP of from about 0.15 to about 0.64, preferably from about 0.25 to about 0.62, and more preferably from about 0.40 to about 0.60, said principal solvent preferably being at least somewhat asymmetric, and preferably having a melting, or solidification, point that allows it to be liquid at, or near room temperature. Solvents that have a low molecular weight and are biodegradable are also desirable for some purposes. The more assymetric solvents appear to be very desirable, whereas the highly symmetrical solvents such as 1,7- heptanediol, or l,4-bis(hydroxymethyl) cyclohexane, which have a center of symmetry, appear to be unable to provide the essential clear compositions when used alone, even though their ClogP values fall in the preferred range.

Operable principal solvents are disclosed and listed below which have ClogP values which fall within the requisite range. These include mono-ols, C6 diols, C7 diols, octanediol isomers, butanediol derivatives, trimethylpentanediol isomers, ethylmethylpentanediol isomers, propyl pentanediol isomers, dimethylhexanediol isomers, ethylhexanediol isomers, methylheptanediol isomers, octanediol isomers, nonanediol isomers, alkyl glyceryl ethers, di(hydroxy alkyl) ethers, and aryl glyceryl ethers, aromatic glyceryl ethers, alicyclic diols and derivatives, C3C7 diol alkoxylated derivatives, aromatic diols, and unsaturated diols. Particularly preferred principal solvents include hexanediols such as 1,2-Hexanediol and 2-Ethyl-l,3-hexanediol and pentanediols such as 2,2,4-Trimethyl-l,3-pentanediol. These principal solvents are all disclosed in copending U.S. Patent application numbers 08/621,019; 08/620,627; 08/620,767; 08/620,513; 08/621,285; 08/621,299; 08/621,298; 08/620,626; 08/620,625; 08/620,772; 08/621,281; 08/620,514; and 08/620,958, all filed March 22, 1996 and all having the title "CONCENTRATED, STABLE, PREFERABLY CLEAR, FABRIC SOFTENING COMPOSITION", the disclosures of which are all herein incorporated by reference.

Especially preferred for use in the hair conditioning compositions herein is 1,2- hexanediol.

Quaternary Ammonium Conditioning Agent

A second essential ingredient of the compositions herein is a quaternary ammonium conditioning agent, preferably present at a level of from about 1% to about 25%, preferably from about 5% to about 20%, more preferably from about 5% to about 15%, by weight of the conditioning composition.

An essential substituted quaternary ammonium compound for use herein may be defined a Diester Quaternary Ammonium active (DEQA) selected from compounds having the formula:

(R)4-m - N(⁺) - [(CH₂)_n - Y- R ¹]m r(^")

0)

wherein each R substituent is a short chain Cι -C6, preferably C1-C3 alkyl or hydroxyalkyl group, e.g., methyl (most preferred), ethyl, propyl, hydroxyethyl, and the like, benzyl, or mixtures thereof; each m is 2 or 3; each n is from 1 to about 4; each Y is -O-(O)C-, or -C(O)-O-; the sum of carbons in each R , plus one when Y is -O-(O)C-, is C12-C22, preferably C14-C20, with each R¹ being a hydrocarbyl, or substituted hydrocarbyl, group, preferably, alkyl, monounsaturated alkylene, or polyunsaturated alkylene, preferably the conditioning active containing poiyunsaturated alkylene groups present at a level of least about 3%, preferably at least about 5%, more preferably at least about 10%, and even more preferably at least about 15%, by weight of the total softener active present (As used herein, the "percent of softener active" containing a given R! group is the same as the percentage of that same R group is to the total R^ groups used to form all of the softener actives.); and wherein the counterion, X", can be any softener-compatible anion, preferably, chloride, bromide, methyl sulfate, or nitrate, more preferably chloride;

As used herein, the Iodine Value of a "parent" fatty acid, or "corresponding" fatty acid, is used to define a level of unsaturation for an R^ group that is the same as the level of unsaturation that would be present in a fatty acid containing the same Rl group. The Iodine Value (hereinafter referred to as IV) of the parent fatty acids of these R! group is preferably from about 60 to about 140, more preferably from about 70 to about 130; and even more preferably from about 75 to about 115, on the average. It is believed that the actives which comprise unsaturated R! groups are preferably from about 50% to about 100%, more preferably from about 55% to about 95%, and even more preferably from about 60% to about 90%, by weight of the total active present. The actives containing polyunsaturated Rl groups are at least about 3%, preferably at least about 5%, and more preferably at least about 10%, and yet more preferably at least about 15%, by weight, of the total actives present. These polyunsaturated groups are necessary to provide optimum viscosity stability, especially after freezing and thawing. The higher the level of polyunsaturated R groups in the actives, the lower the level of actives which comprise unsaturated R* groups can be.

The counterion, X'^"-) above, can be any active-compatible anion, preferably the anion of a strong acid, for example, chloride, bromide, methylsulfate, sulfate, nitrate and the like, and more preferably chloride.

These quaternary ammonium conditioning compounds preferably contain the group C(O)R which is derived, primarily from unsaturated fatty acids, e.g., oleic acid, the essential polyunsaturated fatty acids, and/or saturated fatty acids, and/or partially hydrogenated fatty acids from natural sources, e.g., derived from vegetable oils and/or partially hydrogenated vegetable oils, such as, canola oil, safflower oil, peanut oil, sunflower oil, corn oil, soybean oil, tall oil, rice bran oil, etc. In other preferred embodiments, the fatty acids have the following approximate distributions, the comparative DEQAs being similar to those described in the art: Fattv Acvl Group DEOA¹ DEOA² DEOA³ DEOA⁴ DEOA⁵

C12 trace trace 0 0 0

C14 3 3 0 0 0

C16 4 4 5 5 5

C18 0 0 5 6 6

C14:l 3 3 0 0 0

C16:l 11 7 0 0 3

C18:l 74 73 71 68 67

C18:2 4 8 8 11 11

C18:3 0 1 1 2 2

C20:l 0 0 2 2 2

C20 and up 0 0 2 0 0

Unknowns 0 0 6 6 7

Total 99 99 100 100 102

IV 86-90 88-95 99 100 95 cis/trans (C18:l) 20-30 20-30 4 5 5

TPU 4 9 10 13 13

Nonlimiting examples of DEQA's are as follows:

Fattv Acvl Group DEOA⁶ DEOA⁷

C14 0 1

C16 11 25

C18 4 20

C14:l 0 0

C16:l 1 0

C18:l 27 45

C18:2 50 6

C18:3 7 0

Unknowns 0 3

Total 100 100

IV 125- 138 56 cis/trans (C18:l) Not 7

Available

TPU 57 6 DEQA⁶ is prepared from a soy bean fatty acid, and DEQA⁷ is prepared from a slightly hydrogenated tallow fatty acid.

It is preferred that at least a majority of the fatty acyl groups are unsaturated, e.g., from about 50% to 100%, preferably from about 55% to about 95%, more preferably from about 60% to about 90%, and that the total level of active containing polyunsaturated fatty acyl groups (TPU) be from about 3% to about 30%, preferably from about 5% to about 25%, more preferably from about 10% to about 18%. The cis/trans ratio for the unsaturated fatty acyl groups is important, with a cis/trans ratio of from 1:1 to about 50:1, the minimum being 1:1, preferably at least 3:1, and more preferably from about 4: 1 to about 20: 1.

The highly unsaturated materials are also easier to formulate into concentrated premixes that maintain their low viscosity and are therefore easier to process, e.g., pump, mixing, etc. These highly unsaturated materials with only a low amount of solvent that normally is associated with such materials, i.e., from about 5% to about 20%, preferably from about 8% to about 25%, more preferably from about 10% to about 20%, weight of the total conditioning active/solvent mixture, are also easier to formulate into concentrated, stable dispersion compositions of the present invention, even at ambient temperatures. This ability to process the actives at low temperatures is especially important for the polyunsaturated groups, since it mimimizes degradation. Additional protection against degradation can be provided when the compounds and conditioning compositions contain effective antioxidants and/or reducing agents, as disclosed hereinafter.

It will be understood that substituents R and R* can optionally be substituted with various groups such as alkoxyl or hydroxyl groups, so long as the R¹ groups maintain their basically hydrophobic character. The preferred compounds can be considered to be biodegradable diester variations of ditallow dimethyl ammonium chloride (hereinafter referred to as "DTDMAC"), which is a widely used fabric softener. A preferred long chain DEQA is the DEQA prepared from sources containing high levels of polyunsaturation, i.e., N,N-di(acyl-oxyethyl)-N,N-dimethyl ammonium chloride, where the acyl is derived from fatty acids containing sufficient polyunsaturation.

As used herein, when the diester is specified, it can include the monoester that is present. Preferably, at least about 80% of the DEQA is in the diester form, and from 0% to about 20% can be DEQA monoester (e.g., in formula (1), m is 2 and one YRI group is either "H" or "-C-(O)-OH"). The overall ratios of diester to monoester are from about 100:1 to about 2: 1, preferably from about 50: 1 to about 5:1, more preferably from about 13:1 to about 8:1. The level of monoester present can be controlled in manufacturing the DEQA.

The above compounds, used as the quatemized ester-amine conditioning active in the practice of this invention, can be prepared using standard reaction chemistry. In one synthesis of a di-ester variation of DTDMAC, an amine of the formula RN(CH2CH2OH)2 is esterified at both hydroxyl groups with an acid chloride of the formula R¹C(O)Cl, then quatemized with an alkyl halide, RX, to yield the desired reaction product (wherein R and R¹ are as defined hereinbefore). However, it will be appreciated by those skilled in the chemical arts that this reaction sequence allows a broad selection of agents to be prepared. Preferred methods of making the ester-substituted quaternary ammonium compounds herein is to be found in WO98/03618, incorporated herein by reference. In particular, WO98/03618 teaches a process of manufacture which comprises the steps of: a) providing a source of triglyceride and reacting said source of triglyceride to form a mixture, said mixture comprising fatty acids having the formula RICO2H, fatty acid esters having the formula RICO2R", or mixtures thereof; wherein Rl is C1-C22 alkyl, C2-C22 alkenyl, and mixtures thereof; R" is C1-C4 alkyl, C2-C4 monohydroxyalkyl, C3-C4 dihydroxyalkyl; b) reacting said mixture from step (a) with one or more amines having the formula:

wherein R is C1 -C alkyl, Ci-Cg hydroxyalkyl, benzyl, or mixtures thereof; each Z is independently selected from the group consisting of -OH, -CHR'OH, -CH(OH)CH₂OH, -NH₂, and mixtures thereof, wherein R' is C1-C4 alkyl; m is an integer from 1 to 3; n is an integer from 1 to 4; to form a fabric softening active precursor mixture having the formula:

wherein R, Rl, m, and n are the same as above; Y has the formula: — 0

or mixtures thereof; wherein R and R' are the same as above; and c) quaternizing said fabric softening active precursor mixture from step (b) by reacting said mixture with a quaternizing agent of the formula RX, wherein R is the same as defined in step (b) and X is a softener compatible anion, forming a fabric softening active having the formula:

X

wherein R, R^, X, Y, m, and n are the same as above; provided at least step (c) is carried out in the presence of a chelating agent selected from the group consisting of diethylenetriaminepentaacetic acid, ethylenediamine-N,N'-disuccinnic acid, and mixtures thereof. Preferably, both steps b and c are carried out in the presence of chelant.

An example of a preferred amine starting material taught in WO98/03618 for use in Step (b) is the symmetrical triamine, triethanol amine, having the formula:

which can be represented by the generic formula:

wherein Z is -OH and n is equal to 2. Reaction, preferably a transesterification reaction between fatty acid esters of the triglyceride source and the triamine, yields a softener active precursor mixture having the general formula:

wherein the composition of alkyl units which comprise R is determined by the choice of the triglyceride source, and n is equal to 2. For example, WO98/03618 teaches that a preferred source of triglyceride is canola oil. Reaction of this triglyceride source, preferably by transesterification to the mixture of canola fatty acid methyl esters, provides a suitable feedstock for reaction with triethanol amine in Step (b) of the present process.

Quaternization is carried out under conditions and with reactants generally familiar to those experienced in this field. WO98/03618 teaches quaternizing agent of the formula RX, wherein R is preferably methyl, benzyl, or ethyl, and X is a softener-compatible anion, preferably where RX is methyl chloride, benzyl chloride, dimethyl sulfate, or diethyl sulfate.

Yet another DEQA active that is suitable for the formulation of the conditioning compositions of the present invention, has the above formula (1) wherein one R group is a Cι_4 hydroxy alkyl group, preferably one wherein one R group is a hydroxyethyl group. An example of such a hydroxyethyl ester active is di(acyloxyethyl)(2-hydroxyethyl)methyl ammonium methyl sulfate, where the acyl is derived from the fatty acids described hereinbefore. Another example of this type of DEQA is derived from the same fatty acid as that of DEQA^, and is denoted hereinafter as DEQA .

The DEQA actives described hereinabove can contain a low level of the fatty acids which can be unreacted starting material and/or by-product of any partial degradation, e.g., hydrolysis, of the actives in the finished compositions. It is preferred that the level of free fatty acid be low, preferably below about 10%, more preferably below about 5%, by weight of the active.

Particularly preferred conditioning actives and their methods of preparation are disclosed in US Application No. 60/044719.

A commercially available diester quaternary ammonium compound for use herein has the tradename Tetranyl Co-40 and is supplied by Kao. The INCI name for this material is Dioleylethyl Hydroxyethylmonium methosulfate. The quaternary ammonium conditioning agent, is preferably present at a level of from about 1% to about 25%, preferably from about 5% to about 20%, more preferably from about 5% to about 15%, by weight of the conditioning composition.

Optional Components

The conditioning compositions herein can contain a wide variety of optional ingredients, non-limiting examples of which are described hereinbelow.

The conditioning compositions herein can comprise an emollient selected from polyethylene glycol derivatives of triglyceride, polypropylene and polyethylene glycol ethers of glucose and polypropylene glycol ethers of fatty alcohol, and mixtures thereof, preferably a water-soluble emollient. The compositions preferably comprise from about 0.1% to about 10%, preferably 0.1% to about 5%, by weight, of the emollient.

Polyethylene glycol derivatives of glycerides

Suitable polyethylene glycol derivatives of glycerides include any polyethylene glycol derivative of glycerides which are water-soluble and which are suitable for use in a hair conditioning composition. Suitable polyethylene glycol derivatives of glycerides for use herein include derivatives of mono-, di- and tri-glycerides and mixtures thereof.

One class of polyethylene glycol derivatives of glycerides suitable herein are polyethyleneglycol glyceryl fatty esters having the formula (1):

RCOCH₂CH(OH) CH₂ (OCH₂CH₂) _nOH

wherein n, the degree of ethoxylation, is from about 4 to about 200, preferably from about 5 to about 100, more preferably from about 6 to about 80, and wherein R comprises an aliphatic radical having from about 5 to about 25 carbon atoms, preferably from about 7 to about 20 carbon atoms.

Suitable polyethylene glycol derivatives of glycerides include PEG-20 almond glycerides, PEG-60 almond glycerides, PEG- 11 avocado glycerides, PEG-6 capric/caprylic glycerides, PEG-8 capric/caprylic glycerides, PEG-20 com glycerides, PEG-60 com glycerides, PEG-60 evening primose glycerides, PEG-7 glyceryl cocoate, PEG-30 glyceryl cocoate, PEG-40 glyceryl cocoate, PEG-78 glyceryl cocoate, PEG-80 glyceryl cocoate, PEG-12 glyceryl dioleate, PEG-15 glyceryl isostearate, PEG-20 glyceryl isostearate, PEG-30 glyceryl isostearate, PEG-75 cocoa butter glycerides, PEG-20 hydrogenated palm oil glycerides, PEG- 70 mango glycerides, PEG- 13 mink glycerides, PEG-75 shorea butter glycerides, PEG-10 olive glycerides, PEG-12 palm kernal glycerides, PEG-45 palm kernal glycerides, PEG-8 glyceryl laurate and PEG-30 glyceryl laurate. Mixtures of polyethylene glycol derivatives of glycerides can also be used herein.

Preferred for use herein is a polyethylene glycol derivative of sunflower oil commerically available from Floratech under the tradename Florasun PEG-10.

Polyalkylene glycol ether of a glucose

Suitable polyalkylene glycol ethers of glucose for use herein include any water- soluble polyalkylene glycol ether of glucose suitable for use in a hair conditioning composition. Preferred herein are polyethylene glycol ether and polypropylene glycol ethers of glucose. Suitable examples include PPG- 10 methylglucose ether, PPG-20 ethyl glucose ether, Methyl Gluceth-20 and Methyl Gluceth-10. Mixtures of polyalkylene glycol ethers of glucose can also be used herein.

Polypropylene glycol ether of fatty alcohol

Suitable polypropylene glycol ethers of fatty alcohol for use herein include any water- soluble polypropylene glycol ether of fatty alcohol suitable for use in a hair conditioning composition. Suitable examples include PPG-3 myristylether and PPG- 2 myristyl ether propionate. Mixtures of polypropylene glycol ethers of fatty alcohols can also be used herein.

Most preferred for use in the compositions herein is a polypropylene glycol ether of a glyceride.

The conditioning compositions of the present invention optionally comprise from about 0.1% to about 10%, preferably from about 1% to about 5%, more preferably from about 2% to about 4%, by weight of the composition of water soluble organic solvent which does not have the appropriate ClogP value given above. Suitable such organic solvents for use herein are e.g., ethanol; isopropanol; 1,2-propanediol; 1,3- propanediol; propylene carbonate, butylene glycol, etc., preferably 1,3-butylene glycol.

The hair conditioning compositions herein can also comprise a wide variety of additional ingredients which are known for use in conventional hair conditioning compositions, non-limiting examples of which are given below.

The conditioning compositions herein may contain one or more monohydric fatty alcohols. Suitable fatty alcohols for use herein are fatty alcohols having a melting point of 30°C or lower being preferably selected from unsaturated straight chain fatty alcohols, saturated branched chain fatty alcohols, saturated Cg-C^ straight chain alcohols, and mixtures thereof. When present the fatty alcohol is preferably used at a level of from about 0.1% to about 10%, by weight, preferably from about 0.1% to about 5%, more preferably from about 0.25% to about 1%.

The unsaturated straight chain fatty alcohols will typically have one degree of unsaturation. Di- and tri- unsaturated alkenyl chains may be present at low levels, preferably less than about 5% by total weight of the unsaturated straight chain fatty alcohol, more preferably less than about 2%, most preferably less than about 1%.

Preferably, the unsaturated straight chain fatty alcohols will have an aliphatic chain size of from C12-C22 more preferably from Ci2-Cιg, most preferably from C\ - Cjg. Especially preferred alcohols of this type include oleyl alcohol and palmitoleic alcohol.

The branched chain alcohols will typically have aliphatic chain sizes of from C12- C22, preferably C14-C20, rnore preferably Ci o-Cjg- Exemplary branched chain alcohols for use herein include isostearyl alcohol, octyl dodecanol, and octyl decanol.

Examples of saturated Cg-Ci2 straight chain alcohols include octyl alcohol, caprylic alcohol, decyl alcohol, and lauryl alcohol.

The present compositions are preferably limited to levels of fatty alcohols, such as cetyl alcohol and stearyl alcohol, of no more than about 5%, preferably no more than about 1%, more preferably 0%, by weight of the composition. The conditioning compositions herein may also comprise from about 0.1% to about 10%, by weight, preferably from about 0.2% to about 5%, more preferably from about 0.5% to about 3%, of a polymer of ethylene oxide, propylene oxide, and mixtures thereof, having the general formula:

H(OCH₂CH)n— OH R wherein R is selected from the group consisting of H, methyl, and mixtures thereof; and n has an average value of from about 2,000 to about 14,000, preferably from about 5,000 to about 9,000, more preferably from about 6,000 to about 8,000. When R is H, these materials are polymers of ethylene oxide, which are also known as polyethylene oxides, polyoxyethylenes, and polyethylene glycols. When R is methyl, these materials are polymers of propylene oxide, which are also known as polypropylene oxides, polyoxypropylenes, and polypropylene glycols. When R is methyl, it is also understood that various positional isomers of the resulting polymers can exist. In the above structure, n has an average value of from about 2,000 to about 14,000, preferably from about 5,000 to about 9,000, more preferably from about 6,000 to about 8,000.

Polyethylene glycol polymers useful herein that are especially preferred are PEG-2M wherein R equals H and n has an average value of about 2,000 (PEG 2-M is also known as Polyox WSR® N-10 from Union Carbide and as PEG-2,000); PEG-5M wherein R equals H and n has an average value of about 5,000 (PEG 5-M is also known as Polyox WSR® N-35 and Polyox WSR® N-80, both from Union Carbide and as PEG-5,000 and Polyethylene Glycol 300,000); PEG-7M wherein R equals H and n has an average value of about 7,000 (PEG 7-M is also known as Polyox WSR® N-750 from Union Carbide); PEG-9M wherein R equals H and n has an average value of about 9,000 (PEG 9-M is also known as Polyox WSR® N-3333 from Union Carbide); and PEG- 14 M wherein R equals H and n has an average value of about 14,000 (PEG 14-M is also known as Polyox WSR® N-3000 from Union Carbide.)

Other useful polymers include the polypropylene glycols and mixed polyethylene/polypropylene glycols.

The compositions herein can comprise conditioning agents in addition to the quaternary ammonium conditioning agents described hereinabove. Suitable conditioning agents include cationic surfactants, cationic polymers, nonvolatile silicones, nonvolatile hydrocarbons, saturated C14 to C22 straight chain fatty alcohols, nonvolatile hydrocarbon esters, and mixtures thereof. Suitable conditioning agents are disclosed in WO95/20939 which is incorporated herein by reference.

A wide variety of additional ingredients can be formulated into the present conditioning compositions. These include hair-hold polymers, detersive surfactants such as anionic, nonionic, amphoteric, and zwitterionic surfactants, additional viscosity modifying agents and suspending agents such as xanthan gum, guar gum, hydroxypropyl guar, hydroxyethyl cellulose, methyl cellulose, hydroxyethylcellulose, starch and starch derivatives; viscosity modifiers such as methanolamides of long chain fatty acids such as cocomonoethanol amide; crystalline suspending agents; pearlescent aids such as ethylene glycol distearate; preservatives such as benzyl alcohol, methyl paraben, propyl paraben and imidazolidinyl urea; polyvinyl alcohol; ethyl alcohol; pH adjusting agents, such as citric acid, sodium citrate, succinic acid, phosphoric acid, sodium hydroxide, sodium carbonate; salts, in general, such as potassium acetate and sodium chloride; coloring agents, such as any of the FD&C or D&C dyes; hair oxidizing (bleaching) agents, such as hydrogen peroxide, perborate and persulfate salts; hair reducing agents, such as the thioglycolates; perfumes; sequestering agents, such as disodium ethylenediamine tetra-acetate; and polymer plasticizing agents, such as glycerin, disobutyl adipate, butyl stearate, and propylene glycol. Such optional ingredients generally are used individually at levels from about 0.01% to about 10.0%, preferably from about 0.05% to about 5.0% by weight of the composition.

The conditioning compositions herein can be formulated in a wide variety of product forms, including but not limited to creams, gels, aerosol and non-aerosol foams, mousses and sprays. Mousses, foams and sprays can be formulated with propellants such as propane, butane, pentane, dimethylether, hydroflurocarbon, CO2, N2O, or without propellants (using air as the propellant in a pump spray or pump foamer package).

METHOD OF USE

The conditioning composition herein may be used in a conventional manner for conditioning human hair. Preferably after shampooing, an effective amount of the conditioner composition, typically from about 1 gram to about 50 grams, preferably from about 1 gram to about 25 grams, is then applied to the hair. Application of the conditioner typically includes working the composition through the hair, generally with the hands and fingers, or with a suitable implement such as a comb or brush. The conditioner composition is preferably then rinsed from the hair with water, but can also be left on the hair..

The preferred method for conditioning the hair therefore comprises the steps of: (a) applying an effective amount of the conditioning composition to hair which has been shampooed, (b) working the conditioning composition into the hair with hands and fingers or with a suitable implement, (g) rinsing the conditioning composition from the hair using water.

These steps can be repeated as many times as desired to achieve the conditioning benefit sought, preferably only once.

In an alternative method herein the conditioner herein can be left on the hair instead of being rinsed out.

EXAMPLES

The following examples further describe and demonstrate embodiments within the scope of the present invention.

Preparation

The conditioning compositions of the present invention can be prepared by using conventional mixing and formulating techniques.

Conditioning Compositions I- VIII

Foam Spray Mousse Gel

Ingredient I/% II/% III/% IV/%

Tetranyl Co-40 (80% 12.5 3.1 12.5 12.5 active)¹

1,2-Hexanediol 10 10 10 5

Methylparaben 0.2 0.2 0.2 0.2

Propylparaben 0.1 0.1 0.1 0.1 1,3 Butylene glycol 2 2 2 2

Perfume 1 1 1 1

Dimethicone copolyol 0.1 0.1 0.1 0.1

(SF1188A)⁵ Florasun PEG-10² 2 2 2 2 Jaguar HP- 105 0 0 0 0

Tiθ2 (40% in 1,3-butylene 0 0 0 0 glycol)

AP 30 Propellant⁴ 0 4.3

Water -to 100-

Foam Mousse Gel Opacified Gel

Ingredient V/% VI/% VII/% VIII/% Tetranyl Co-40 (80% 12.5 3.1 18 18 active)

1,2-Hexanediol 10 10 5 5 Methylparaben 0.2 0.2 0.2 0.2 Propylparaben 0.1 0.1 0.1 0.1 1,3 Butylene glycol 2 2 2 2 Perfume 1 1 1 1

Dimethicone copolyol 0.1 0.1 0.1 0.1 (SF1188A)⁵ Florasun PEG-10² 2 2 2 2

Jaguar HP- 105^ 0 0 0 0

Tiθ2 (40% in 1,3-butylene 0 0 0 0.25 glycol)

AP 30 Propellant⁴ 0 4.3 0 0

Hexylene Glycol 0.75 0.75 0.75 0.75

Ethanol 0.75 0.75 0.75 0.75

Water » i nn

1. Supplied by Kao

2. Supplied by Floratec 3. Supplied by Rhone Poulenc

4. mixture of propane, isobutane, n-butane supplied by BP

5. Supplied by GE Silicones

Process for preparation of conditioner liquid/gel

The Tetranyl Co-40 and hexanediol are added to the mixing vessel. Agitation is begun slowly. The butylene glycol is added and heated to 40°C. Agitation is continued and the methyl and propyl paraben is added at 40°C and allowed to dissolve. The composition is then cooled. With agitation the remaining ingredients are added while cooling. The perfume is added at about 25°C. The water is added and mixed until homogeneous. The pH is adjusted to 3.5 with sodium hydroxide.

Process for preparation of Foam

The resulting conditioner liquid is put into a pump foamer package such as ATRSPRAY supplied by Zuiderkade.

Process for preparation of aerosol mousse

To a 150ml aluminium can, 132ml of the above liquid concentrate is added. The can is crimped and a vacuum is drawn. 6g of propellant is added.

Process for preparation of spray

The resulting liquid concentrate is put into a suitable spray gel can.

The conditioning compositions of the examples provide excellent hair detangling and wet clean feel on rinsing and post rinsing with the additional benefits of minimizing volume loss.

Claims

Claims:

1. Method of conditioning the hair comprising applying to the hair an effective amount of a conditioner composition wherein the conditioner composition comprises:

(a) a mono-ol or diol solvent having a ClogP of from about 0.15 to about 0.64;and (b) quaternary ammonium cationic conditioning agent having the formula (I):

(R)₄-m - N(⁺) - [(CH₂)n -Y- R ¹]m r(^")

(1)

wherein each R substituent is a short chain Cj-Cg alkyl or hydroxyalkyl group, benzyl, or mixtures thereof; each m is 2 or 3; each n is from 1 to about 4; each Y is -O-(O)C-, or -C(O)-O-; each Rl is a hydrocarbyl, or substituted hydrocarbyl, group, the sum of carbons in each Rl, plus one when Y is -O-(O)C-, being Ci2- C22; the average Iodine Value of the parent fatty acid of the R group being from about 60 to about 140; and wherein the counterion, X" is any softener-compatible anion; the level of conditioning agent containing polyunsaturated alkylene groups being at least about 3% by weight of the total conditioning agent present and wherein the aqueous dispersion comprises a mixture of monoester and diester.

2. Method of conditioning the hair according to Claim 1 wherein the composition comprises from about 0.1% to about 20%, preferably from about 0.5% to about 15%, by weight, of solvent.

3. Method of conditioning the hair according to Claim 1 or 2 wherein the composition comprises from about 0.1% to about 20%, preferably from about 0.5% to about 15%, by weight, of quaternary ammonium cationic conditioning agent.

4. Method of conditioning the hair according to any of Claims 1 to 3 wherein the solvent is a C6 diol, preferably 1,2-hexanediol.

5. A method according to any of Claims 1 to 4 wherein each R substituent is a Cj- C3 alkyl or hydroxyalkyl group, or mixtures thereof; each m is 2 or 3; each n is from 1 to about 4; each Y is -O-(O)C-; the number of carbon atoms in R* plus one is C14-C20; the average Iodine Value of the parent fatty acid of this R* group being from about 70 to about 130; and wherein the counterion, X" is chloride; the total level of polyunsaturated active being at least about 5%;

6. A method according to Claim 5 wherein each R substituent is a Ci -C3 alkyl or hydroxyalkyl group, or mixtures thereof; each m is 2 or 3; each n is 2; the Iodine Value of the parent fatty acid of the R¹ group being from about 80 to about 115; the cis/trans ratio being from about 1 : 1 to about 50: 1; and the total level of polyunsaturated active being at least about 10%.

7. A method according to Claim 6 wherein the quaternary ammonium conditioning agent comprises up to about 20% of monoester compound in which m is 2 and one YR¹ is H or -C(O)OH.