US 2016O158128A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2016/0158128A1 Marsh et al. (43) Pub. Date: Jun. 9, 2016

(54) COMPOSITION FOR HAIR FRIZZ (52) U.S. Cl. REDUCTION CPC. A61 K8/41 (2013.01); A61O 5/12 (2013.01); A61K 8/34 (2013.01); A61 K8/25 (2013.01); (71) Applicant: The Procter & Gamble Company, A61K 8/36 (2013.01); A61 K 2800/70 (2013.01)

(72) Inventors: Jennifer Mary Marsh, Deerfield The present invention is directed to a rinse-off conditioner Township, OH (US); Supriya Punyani, opposition for hair frizz reduction comprising from about Singapore (SG); MuiSlang Soh O.2% to about 20% of a moisture control material Or m1Xture Ingap s g s of moisture control materials wherein the moisture control Singapore (SG); Jiazhen Zhang, - 0 - - - SingaporeIngap (SG); Brian Xiaoqing Song, material is selected from one or more of the following: Mason, OH (US); Tiffany Tien-Yun Yang, Loveland, OH (US) R (21) Appl. No.: 14/959,234 Rs R

(22) Filed: Dec. 4, 2015 R4 R2 Related U.S. Application Data R3 (60) Provisional application No. 62/088,029, filed on Dec. 5, 2014. wherein R is COOY, sulfonic acid, or C=CH-COOY.Y is hydrogen or a metal ion, R. R. R. R. Rs is hydrogen, methyl, ethyl, propyl, vinyl, allyl, methoxy, ethoxy, hydroxyl, Publication Classification halogen, sulfate, sulfonate, nitro, or —CH=CH-COOR, and wherein the moisture control material is an acidic mate (51) Int. Cl. rial and further wherein the moisture control material has a '% A6 IK 8/4I (2006.01) Protein binding higher than 20 and Molecular Volume lower A6 IK 8/36 (2006.01) than 500 and Partition coefficient octanol to water (log P) A6 IK 8/25 (2006.01) lower than 3 and hydrogen binding higher than 10 and pKa A61O5/12 (2006.01) lower than 5.0; and at least about a 4% fizz reduction vs. a A6 IK 8/34 (2006.01) control composition without the moisture control material. Patent Application Publication Jun. 9, 2016 US 2016/0158128A1

y = 1.9265X - 14.212 "S C R2 = 0.89933 {}

fe ce

92 ww.

s s Sir D were

sS. Sn

O 5 2O % Frizz reduction vs CO to: US 2016/01581 28 A1 Jun. 9, 2016

COMPOSITION FOR HAIR FRIZZ wherein R is COOY, sulfonic acid, or C=CH-COOY.Y REDUCTION is hydrogen or a metal ion, R. R. R. R. Rs is hydrogen, methyl, ethyl, propyl, vinyl, allyl, methoxy, ethoxy, hydroxyl, FIELD OF THE INVENTION halogen, sulfate, sulfonate, nitro, or —CH=CH-COOR, 0001. The present invention relates to a rinse off condi and wherein the moisture control material is an acidic mate tioner composition comprising one or more materials useful rial and further wherein the moisture control material has a '% for treating hair frizz. Protein binding higher than 20 and Molecular Volume lower than 500 and Partition coefficient octanol to water (log P) BACKGROUND OF THE INVENTION lower than 3 and hydrogen binding higher than 10 and pKa lower than 5.0; and at least about a 4% fizz reduction vs. a 0002 Hair frizz is described by consumers as the appear control composition without the moisture control material. ance of unruly fibers at the top of the scalp and tips of hair as 0006 Without being bound by theory, the materials in the well as an increased volume through the bulk of the hair. conditioner treatment composition of the present invention Generally they see this frizz on days when there is humid provide excellent frizz performance without a negatively weather and the level of moisture in the air is high. The affecting hair feel. These materials prevent water uptake into appearance of frizZ is undesired and it is often associated with hair under high humidity conditions, reducing the negative a loss of shine and Smoothness. The appearance of frizz and impact of frizz. By providing frizz benefits by penetrating the loss of shine and Smoothness are associated with a perception hair fiber as opposed to depositing on the hair Surface, the of poor hair health. The basic mechanism causing frizzin high frizz benefit is not associated by negative hair feel, which is humid environments is that at high humidity water penetrates typically observed with current commercial anti-frizz prod into hair and changes the chemical bond interactions inside ucts. These and additional features provided by the embodi the hair. During styling, the consumer will create a wet set ments of the present invention will be more fully understood where hair is blow dried or flat ironed to create the desired in view of the following detailed description. shape. During drying, water is evaporated from hair and hydrogen bonds are formed between the protein peptide BRIEF DESCRIPTION OF THE DRAWINGS chains holding the style in place. As moisture diffuses into hair the hydrogenbonds are broken and hair returns back to its 0007 FIG. 1 is graph depicting that there is a monotonic natural shape. For consumers who straighten their hair by correlation between% water reduction and% frizz reduction. blow drying or flat ironing this return to a curled style is associated with a loss of alignment and increased Volume. In DETAILED DESCRIPTION OF EMBODIMENTS addition, at high moisture levels in hair the fiber diameter OF THE INVENTION increases which also increases the overall volume of hair. 0008 All percentages and ratios used herein are by weight 0003. The typical strategy to prevent frizz is to formulate of the total composition, unless otherwise designated. All conditioner products with Surface-depositing materials such measurements are understood to be made at ambient condi as silicone, oils, conditioning silicone etc. which make hair tions, where 'ambient conditions' means conditions at about more hydrophobic and decrease inter-fiber interactions. At 25°C., under about one atmosphere of pressure, and at about high levels these materials can also provide increased cohe 50% relative humidity (RH), unless otherwise designated. All sive forces holding fibers together to prevent frizzfrom occur numeric ranges are inclusive of narrower ranges; delineated ring. With these materials depositing on the hair Surface a upper and lower range limits are combinable to create further greasy look and feel is typically experienced, which is an ranges not explicitly delineated. undesired trade-off of frizz reduction. 0009. The compositions of the present invention can com 0004 Consequently, a need exists for a conditioner prod prise, consist essentially of or consist of the essential com uct that combines effective frizz control with additional hair ponents as well as optional ingredients described herein. As benefits that the consumer can notice and feeland, at the same used herein, "consisting essentially of means that the com time, is delightful to use without having a sticky or greasy position or component may include additional ingredients, feel. but only if the additional ingredients do not materially alter the basic and novel characteristics of the claimed composi SUMMARY OF THE INVENTION tions or methods. 0005. In an embodiment, a rinse-off conditioner compo 0010 Apply” or “application” as used in reference to a sition for hair frizz reduction comprising: from about 0.2% to composition, means to apply or spread the compositions of about 20% of a moisture control material or mixture of mois the present invention onto keratinous tissue such as the hair. ture control materials wherein the moisture control material is 0011 “Dermatologically acceptable” means that the com selected from one or more of the following: positions or components described are Suitable for use in contact with human skin tissue without undue toxicity, incompatibility, instability, allergic response, and the like. R 0012 “Safe and effective amount’ means an amount of a compound or composition Sufficient to significantly induce a positive benefit 0013 “Control composition' is a composition that is used for comparison to the inventive composition in terms of per formance. Typically, the control composition and the inven tive composition are very similar in terms of ingredients and concentrations with the difference being that control compo sition does not include the material or materials that consti US 2016/01581 28 A1 Jun. 9, 2016

tute the invention. Thus, the inventive material(s) that are 0022 “Derivatives, as used herein, includes but is not present in the inventive composition are either substituted by limited to, amide, ether, ester, amino, carboxyl, acetyl, acid, the carrier in the control composition or by a material that is salt and/or alcohol derivatives of a given compound. common in the art at the time of the invention. 0023 “Polymer,” as used herein, means a chemical 0014 “Rinse-off in reference to compositions, means formed from the polymerisation of two or more monomers. compositions intended to be applied to keratinous Substrate The term “polymeras used herein shall include all materials and Subsequently removed by washing, rinsing or wiping made by the polymerisation of monomers as well as natural within a few minutes or less from the application. These polymers. Polymers made from only one type of monomer "rinse-off compositions are to be distinguished from “leave are called homopolymers. Polymers made from two or more on compositions, which are intended to be applied to and different types of monomers are called copolymers. The dis allowed to remain on the keratinous tissue. tribution of the different monomers can be calculated statis 0015 The most common hair care rinse-off compositions tically or block-wise both possibilities are suitable for the are shampoos and rinse-off conditioners. Shampoos contain present invention. Except if stated otherwise, the term “poly detersive Surfactants and they are used for cleansing hair, mer” used herein includes any type of polymer including while rinse-off conditioners are typically used after shampoo, homopolymers and copolymers. they are substantially free of detersive surfactants, they con 0024. The mechanism of action for frizz generation tain conditioning agents to improve hair feel, reverse hair involves moisture from the environment being absorbed by damage and protect against further damage. hair and occupying hydrogen bonding sites within hair, 0016 “Leave-on, in reference to compositions, means including those on the peptide backbone and also associated compositions intended to be applied to and allowed to remain with acidic and basic side chains of amino acid residues such on the keratinous tissue. These leave-on compositions are to as lysine, arginine and glutamic acid. This internal water be distinguished from compositions, which are applied to the replaces hydrogen bonds that had been created during styling hair and Subsequently (in a few minutes or less) removed that hold hair in a desired configuration. As a consequence, either by washing, rinsing, wiping, or the like. Leave-on hair returns to its natural shape which typically leads to compositions exclude rinse-off applications such as sham unwanted wave, loss of alignment and frizZ. In addition, poos, rinse-off conditioners, facial cleansers, hand cleansers, uptake of water by these hydrogen bonding sites Swells the body wash, or body cleansers. The leave-on compositions hair fiber causing style expansion, which is another indicator may be substantially free of cleansing or detersive Surfac offizz. Without being bound by theory, the materials covered tants. For example, “leave-on compositions” may be left on by this invention will replace water at the hydrogenbond sites the keratinous tissue for at least 15 minutes. For example, inside hair and prevent water uptake. Reduction of water leave-on compositions may comprise less than 1% detersive inside hair will lead to a reduction in the appearance of frizz surfactants, less than 0.5% detersive surfactants, or 0% deter under high humidity conditions. Because the mechanism of sive Surfactants. The compositions may, however, contain action is related to the space inside the hair fibers, there are no emulsifying, dispersing or other processing Surfactants that feel negatives. Such as, for example, greasy or oily feel asso are not intended to provide any significant cleansing benefits ciated with the benefit. The reduction in water uptake is when applied topically to the hair. measured using Dynamic Vapor Sorption (DVS) method, which measures a weight increase of hair equilibrated at 0% 0017 “Soluble” means at least about 0.1 g of solute dis Relative Humidity (RH) versus 90% RH. Significant frizz solves in 100 ml of solvent, at 25°C. and 1 atm of pressure. benefit is measured on hair treated by materials that caused a 0018 All percentages are by weight of the total composi reduction in water uptake of higher than 5% versus control tion, unless stated otherwise. All ratios are weight ratios, hair that is not treated with such materials. The treatment unless specifically stated otherwise. All ranges are inclusive involved the application of a 2% w/w solution of the material and combinable. The number of significant digits conveys in 50:50 water:ethanol solvent. neither a limitation on the indicated amounts nor on the accu 0025 Preferred materials include salicylic acid, 2,3-dihy racy of the measurements. The term “molecular weight” or droxybenzoic acid, 2,6-dihydroxybenzoic acid, 3-aminoben “M.Wt” as used herein refers to the weight average molecu Zoic acid, gallic acid, ethyl gallate, 5-chlorosalicylic acid, lar weight unless otherwise stated. The weight average trans-ferulic acid, p-coumaric acid, ricinoleic acid, isovaleric molecular weight may be measured by gel permeation chro acid, isobutyric acid, 2-hexyl-1-decanol, phytol and Sorbitan matography. “QS’ means sufficient quantity for 100%. caprylate. These materials are chosen from Molecular Class I 0019. The term “substantially free from' or “substantially and/or Molecular Class II or can also be used in combination free of as used herein means less than about 1%, or less than to increase the size of the benefit. about 0.8%, or less than about 0.5%, or less than about 0.3%, 0026. In an embodiment of the present invention, the con or about 0%, by total weight of the composition. centration of the Moisture Control Material or the concentra 0020 "Hair, as used herein, means mammalian hair tion of the mixture of Moisture Control Material in a hair including scalp hair, facial hair and body hair, particularly on conditioner composition is from about 0.2% to about 20%, in hair on the human head and scalp. an embodiment from about 0.5% to about 8.0%, and in a 0021 “Cosmetically acceptable,” as used herein, means further embodiment from about 0.5% to about 5.0%. that the compositions, formulations or components described Molecular Class I: Polar, Acidic Compounds with the Fol are Suitable for use in contact with human keratinous tissue lowing Properties: without undue toxicity, incompatibility, instability, allergic (0027 Protein Binding (PB)>20 AND Molecular Volume response, and the like. All compositions described herein (Mol. Vol).<500 AND log P<3 AND Hydrogen-binding which have the purpose of being directly applied to kerati (H-binding)>10 AND pKa<5.0, wherein PB is % protein nous tissue are limited to those being cosmetically accept binding, Mol. Vol is molecular volume (in A); log P is able. n-octanol/water partition coefficients. These properties can US 2016/01581 28 A1 Jun. 9, 2016

be calculated using Volsurf software (http://www.moldiscov -continued ery.com/soft Volsurf.php). H-bond is the energy from hydro gen bonds between molecules from Hansen Solubility % water Parameters and pKa value is a logarithmic measure of the acid Mol. H-bond reduc dissociation constant. Name PB Vol. logP pKa (MPa /2) tion Glyceryl monooleate 96 974 6.27 12.8 16.2 5 Isostearyl 1OO 1527 14.7 14 4.2 11 %. Water isostearate Mol. log H-bond Reduc Ethyl linoleate 82 903 7.71 7.8 S.1 8 Name (1% wt vol) PB Vol. P pKa (MPa /2) tion Isopropyl myristate 97 798 6.99 8.8 S.O 12 Octyl salicylate 82 646 5.4 7.1 11.7 14 2,4-Dihydroxybenzoic 28 324 1.5 3.2 23 30 acid 3-Hydroxybenzoic Acid 38 314 1.6 4.3 2O 2O A Class I having the structure selected from: Gallic acid 23 337 O.9 4.4 23 15 3-Aminobenzoic acid 41 326 O.9 3.6 16 12 0029. 1) Class I having the structure selected from: 4-Aminobenzoic acid 42 323 O.9 3.5 16 12 2,5-Dihydroxybenzoic 31 329 1.6 2.9 23 27 acid R 3,4-Dihydroxybenzoic 27 327 O.9 4.4 23 2O acid Rs R 3,5-Dihydroxybenzoic 27 327 O.9 4.1 23 15 acid 2,6-Dihydroxybenzoic 37 326 1.6 2.1 23 35 acid R4 R2 5-Chlorosalicylic S6 361 2.3 3.0 21 28 acid R3 Salicylic acid 44 32O 2.1 3.1 2O 18 Trans-Ferulic Acid SO 451 1-S 4.5 19 6 p-Counaric acid 46 391 1.6 4.5 2O 8.8 4-Hydroxybenzene- 55 271 1.5 2.7 22 26 wherein R is COOY, Sulfonic acid, or -C=CH-COOY, Sulphonic acid Y is hydrogen or a metalion, R. R. R. R. Rs is hydrogen, 3-Chloro-4- 49 356 2.1 4.1 2O 11 methyl, ethyl, propyl, vinyl, allyl, methoxy, ethoxy, hydroxyl, hydroxybenzoic acid halogen, sulfate, sulfonate, nitro, or —CH=CH-COOR, 3,5-Dichloro-4- 51 397 2.8 3.8 2O 15 hydroxybenzoic acid and wherein the moisture control material is an acidic mate 2.5 Dihydroxytere- 2O 37S 1.1 2.1 22 18 rial and further wherein the moisture control material has a '% phthalic acid Protein binding higher than 20 and Molecular Volume lower 3-Aminophenol 45 284 O.6 4 17 14 3-Hydroxyanilinium 32 280 O.6 4 17 16 than 500 and Partition coefficient octanol to water (log P) chloride lower than 3 and hydrogen binding higher than 10 and pKa 2-Aminophenol 49 288 1.0 4 17 14 lower than 5.0; 4-Aminophenol 39 284 O.6 4 17 10 N-4- 37 388 1.3 3 13 15 0030) 2) Class II having the structure selected from: Hydroxyphenylglycine R10 R12 0028 b) Molecular Class II: Rs COOR Weakly polar to non-polar, weakly to non-acidic compounds R6 that have the following properties: PB>10 AND Mol. Vol. R9 <1500 AND log P-0.5 AND pKad5 AND H-binding>4, R R11 wherein PB is % protein binding, Mol. Vol is molecular volume (in A); log P is n-octanol/waterpartition coefficients. wherein R is hydrogen or metal ion, R is methyl, ethyl, These properties can be calculated using Volsurf software propyl, alkenyl or phenyl having less than 12 carbon atoms (http://www.moldiscovery.com/soft Volsurf.php). H-bond is and wherein R-7, Rs. Ro, Rio R, R2 are hydrogen, methyl, the energy from hydrogen bonds between molecules from ethyl, propyl, phenyl, hydroxyl, methoxy or ethoxy groups; Hansen Solubility Parameters and pKa value is a logarithmic measure of the acid dissociation constant. 0031 b)

R13 R14 % water Mol. H-bond reduc Name PB Vol. logP pKa (MPa /2) tion OH 2-Hydroxyethyl 45 419 1.5 8.3 19.1 10 Salicylate Ethyl gallate 43 431 14 8.7 22.6 17 Oleic Acid 1OO 832 7 5 6.4 14 an alcohol wherein R13 is an alkyl, alkenyl, straight or Ricinoleic acid 84 841 5.9 5 17.8 8.8 branched carbon chains and; and wherein R14 is hydrogen, ISOValeric acid 29 295 1.3 5 9.7 15 hydroxyl, alkyl, methyl, ethyl and propyl wherein the struc Isobutyric acid 15 2S4 1 5 10.4 5 ture of such alcohol contains less than 20 total carbon atoms; 2-Hexyl-1-decanol 87 745 6.8 15 10.1 11 Phytol 1OO 874 8.O 13 9.6 14 0.032 c) An alcohol comprising an unsaturated double Sorbitan caprylate 32 695 13 12 21.8 11 bond in the C2 position. A non limiting example would be phytol. US 2016/01581 28 A1 Jun. 9, 2016

0033 d) an alkyl-substituted glycol wherein the struc 0038. In an embodiment of the present invention, the pH of ture of such alkyl substituted glycol contains less than 20 a composition of the present invention comprising material carbon atoms; from Molecular Class I may be in the range of from about 1 to 0034 e) a monoalkyl or dialkyl substituted glycerin or about 9, in another embodiment a pH of from about 2 to about mono- or di-esters of glycerin with fatty acids wherein 7, in a further embodiment a pH of from about 4 to about 5.5. the structure of such monoalkyl- or dialkyl-substituted 0039. In an embodiment of the present invention, the glycerin or glycerin esters contains less than 20 total Moisture control Material is a carboxylic acid ester. In an carbon atoms; embodiment, the carboxylic acid ester is based on a fatty acid 0035 f) wherein the molecule of the fatty acid comprises of more than 14 carbon atoms. Non-limiting examples of Such esters are isostearyl isostearate, methyl Stearate, methyl palmitate, and HO OH methyl oleate. In another embodiment of the present inven tion, the carboxylic acid ester is part of a mixture of materials prepared via the reaction of natural oils using methanol. Non OH limiting examples of Such mixture is the mixture that is pro OR15 duced by the product of the reaction of refined palm kernel oil with methanol, followed by fractionation via distillation. A commercial product that meets this description is the Heavy wherein Rs could be hydrogen, alkyl, alkenyl, phenyl group Cut Ester CE-1875 (supplied by P&G Chemicals with CAS and wherein the structure of the R group contains less than Number 6772-38-3) containing ingredients such as methyl 20 carbon atoms; Stearate, methyl palmitate, methyl oleate as major ingredi 0036 g) a fatty acid ester containing from 15-40 total ents, as well as methyl laurate, methyl myristate, methyl carbonatoms and wherein the moisture control material behenate and other materials as minor ingredients. of Class II is weakly to non-acidic and further wherein the moisture control material of Class II has protein FORMULATIONS AND EXAMPLES binding higher than 10 and molecular volume lower than 1500 and log Phigher than 0.5 and pKa of 5 or higher 0040. The following are non-limiting examples of the and hydrogen-binding higher than 4. present invention. The examples are given solely for the pur pose of illustration and are not to be construed as limitations pH of Compositions of the present invention, as many variations thereof are pos sible without departing from the spirit and scope of the inven 0037 Below is the data of the difference of% water reduc tion, which would be recognized by one of ordinary skill in tion of hair treated with leave on composition containing 1% the art. salicylic acid in ethanol: water (50:50) at various values of pH vs control (hair treated with composition of ethanol: water EXAMPLES (50:50). As shown in below table, at lower pH, the present invention demonstrates improved performance compared to higher pH. Rinse-Off Conditioner Composition Preparation 0041. The rinse-off conditioner compositions can be pre pared by any conventional method well known in the art. The Formula Example cationic Surfactants and the fatty alcohols are mixed together and heated to from about 66° C. to about 85°C. to forman oil Raw Material pH 3 pH 4.2 pH 7 pH 10 phase. Separately, the disodium EDTA, the Methylchlor Distilled Water QS QS QS QS oisothiazolinone (preservative) and the water are mixed and Ethanol SO.O SO.O SO.O SO.O heated to from about 20° C. to about 48° C. to form an Salicylic acid 1.O 1.O 1.O 1.O Final pH 3.2 4.2 7 10 aqueous phase. The oil phase is mixed into the water phase % Water Reduction 30 27 22 15 under high shear to form the gel matrix. The remaining of the components are added into the gel matrix with agitation. Then, the composition is cooled down to room temperature. TABLE 1.

Rinse-off Conditioner Formulations Formula Example

Control I II III IV V VI. VII VIII (wt., (wt., (wt., (wt., (wt., (wt., (wt., (wt., (wt. wt.) wt.) wt.) wt.) wt.) wt.) wt.) wt.) wt.) Raw Material Active% % % % % % % % % % Benzenemethanaminium, 8O 2.848 2.848 2.848 2.848 2.848 2.848 2.848 2.848 2.848 N.N.N-trimethyl-, chloride (BTMAQIsopropyl Alcohol (IPA) Cetyl Alcohol? 90 1857 1857 1857 1857 1857 1857 1857 1857 1857 Stearyl Alcohol 97 4.643 4.643 4.643 4.643 4.643 4.643 4.643 4.643 4.643 US 2016/01581 28 A1 Jun. 9, 2016

TABLE 1-continued

Rinse-off Conditioner Formulations Formula Example

Control I II III V VI. VII VIII (wt., (wt., (wt., (wt. (wt. (wt., (wt., (wt., (wt. wt.) wt.) wt.) wt.) wt.) wt.) wt.) wt.) Raw Material Active% % % % % % % % % Benzyl Alcohol 99 O400 0.400 0.400 0.400 0.400 O400 0.400 O4(OO O.400 Disodium EDTA, 99 O.127 0.127 0.127 0.127 0.127 0.127 0.127 0.127 0.127 Dihydrate Methylchloroisothiazolinone 1.5 O.O33 O.O.33 O.O33 0.033 O.O.33 O.O.33 O.O33 O.O33 O.O33 (Kathon CG) Terminal Amino 90-100 O.3 O.3 O.3 O.3 O.3 O.3 O.3 O.3 Silicone" Perfume 0.550 0.550 0.550 0.550 0.5SO 0.550 0.550 0.550 0.550 Salicylic acid 99.5 O 1.O O.O O.O O.O O 1 1 5-Chloro 98 O O 1.O O O O O O Salicylic acid 2.4 97 O O O 1 O O O.15 O dihydroxybenzoic acid 9 Isostearyl 100 O O O O O O 1 1 Isostearate' 2-hexyldecanol'? 97 O O O O O 5 O 5 5 Oleic acid 78 O O O O O O2 O O.2 Purified Water Q.S. Q.S. Q.S. Q.S. Q.S. Q.S. Q.S. Q.S. %. Water O6 O.8 O.2 O.9 O.1 2 3 Reduction versus Control at dose of 0.2 g of composition for 1 g of hair % Frizz 7.69 7.79 7.48 7.79 7.84 7.43 841 8.93 Reduction 'Supplied by Feixiang Chemicals (Zhangingang) Co., Ltd. *Supplied by P&G Chemicals Supplied by P&G Chemicals 'Supplied by Ineos Maastricht BV (Maastricht NL) Trilon BDPowder supplied by BASFSE (Ludwigshafen, DE) Kathon CG supplied by Rohm & Haas Co (Philadelphia US) Y-14945 supplied by Momentive Performance Materials *Supplied by API Corpotration 'Supplied by Sigma Algrich 'Supplied by Sigma Algrich Crodamol ISIS supplied by Croda 'Isofol 16 supplied by Sasol (Brunsbuettel, DE) 'Greenolene 6928 supplied by Green Oleo

Rinse-Off Conditioner Hair Treatment Protocol: Evaluation Methods 0045. The hair switches that are treated with the rinse-off 0042 All testing are performed on Caucasian Damaged conditioner compositions are evaluated using the following Frizzy hair Switches weighing approximately 4.0 grams and methodologies. having a length of approximately 6 inches. The hair Switches 0046 a. DVS Measurement are commercially available from IHIP (International Hair 0047. After the hair is exposed to the rinse-off conditioner treatment, it is blow-dried and analyzed for water absorption Importers). Three hair switches per rinse-off compositions desorption as a function of Relative Humidity (RH) according per dosage are used. Each hair Switch is washed with clarify to the following procedure using Dynamic Vapor Sorption ing shampoo followed by a treatment with the rinse-off con (DVS) method. More specifically, the hair switch is weighed ditioner according to the following protocol. and hold for equilibration at 0% RH for 16 hours. After the 16-hour period, the RH is increased to 10% and maintained at 0043. An amount of 0.20g of clarifying shampoo is spread this level for 6 hours. Then, the RH is increased by 10% after via a syringe onto separate hair Switch. That is, the dosage is every 6 hours interval until it reaches 90% RH. The % water 0.10 g of shampoo per g of hair. Each application consists of reduction is calculated as follows: adding shampoo to the hair, milking for 30 seconds followed A=Amount of water absorbed by the hair treated with com by rinsing for 30 seconds. Shampoo is then reapplied (0.1 position containing the Moisture Control Material g/g), milked for 30 seconds and rinsed for 30 seconds. Excess B=Amount of water absorbed by the hair treated with control water is Squeezed from the hair Switches and then 0.1 g/g of composition (only carrier) containing no Moisture Control the rinse-off conditioner is applied and milked for 30 seconds Material and then rinsed for 30 seconds. %Water reduction=(B-A)x100/B 0044) This protocol is repeated for 5 times/cycles. The standard error for DVS measurement is less than 0.05 US 2016/01581 28 A1 Jun. 9, 2016

0048 b. Determination of Frizz Reduction Results 0049. The hair switches are thoroughly blow-dried after the treatment with rinse-off conditioner while holding the 0053 As FIG. 1 demonstrates, there is a monotonic cor hair switch with all the hair fibers at the tip and then the hair relation between% water reduction and% frizz reduction. As Switches are heat straightened by sectioning the hair into material dosage increases, more material penetrates into hair, three parts and then heat with flat iron for 8 passes at 400-450 The % water reduction at high humidity increases resulting in F. Hair switches are then kept at low humidity (between an increase in % frizz reduction i.e. more frizz control. This 20-25% RH) for equilibration for at least an hour. After the confirms the present invention’s technical hypothesis of equilibration period, the hair switches are transferred to high material penetration, interaction with hair protein and humidity chamber (85-90% RH) for frizz assessment. Image decrease of water uptake inside hair at high humidity result of hair switches using a NIR Camera with parallel polarizers ing in frizz control. and are taken immediately after insertion of the hair into the high humidity chamber (to). Another image is taken after 3 Leave-on Treatment Composition Preparation: hours (ts). The pixels are analyzed (selecting the entire hair 0054 The leave-on treatment compositions are prepared switch) for 2D projection of volume (using Vncviewer soft by adding the Moisture Control Materials and perfume, if ware). Then, the mean projected area is determined for the needed, into a 50:50 ethanol/water carrier and stirred until hair Switchatto (A) and for the hair atts (A) and the frizz complete dissolution. The solution pH is adjusted using calculated using the equation given below. Each experiment sodium hydroxide (50% w/w) to a final pH of 4.0-4.2. The is repeated with 3 hair switches. The percent Frizz is calcu Sepigel 305 is then added, if needed, and the solution is mixed lated using below equation: using a high-speed-mixer for 2-5 minutes at 1800-2300 rpm % Frizz 100x(AAoyAo) until a uniform composition is obtained. % Frizz reduction=100x(% Frizz(present invention Leave-on Hair Treatment Protocol: composition)-% Frizz(control composition)/% Frizz(control composition) 0055 An amount of 0.20 g of each composition of The standard error for Frizz measurement is less than 0.1. Examples I to IV is spread via a syringe onto separate natural Virgin brown hair Switches weighing 2.0 g (dosage 0.10 g of Correlation of 9% Frizz Reduction Vs 96 Water Reduction Solution per g of hair). Determined by DVS Methodology 0056. The hair is allowed to air dry and then analyzed 0050 Results obtained from DVS measurements and the using the DVS method described above. The experiment is results from the determination of the frizz reduction method repeated for a dosage of 0.50 g of solution per g of hair. The ology of various Switches indicate that there is a correlation hair in this case is also assessed by expert graders, as between the two methods. In other words, hair switches that described below, in addition to the DVS analysis. show low water reduction also show lower frizz as shown in FIG 1. Hair Switch Feel Assessment Method: 0051 FIG.1 depicting correlation of% water reduction vs 0057 The treated hair switches are kept at high humidity % frizz reduction, where hair switches with different dosage (above 85% RH) for 2 hrs and then ten expert graders are are treated and their% water reduction and % frizz reduction asked to rate each of them in terms of tactile feelbased on a 5 is measured using DVS and frizz method respectively. point scale, 5 being the highest (best feel) and 1 being the 0052 FIG. 1 is a plot depicting that there is a monotonic lowest rating. correlation between% water reduction and% frizz reduction. As material dosage increases, '% water reduction increase Leave-on Treatment Formulation: resulting in increase in % frizz reduction i.e. more frizz con trol. 0.058

Formula Example

Leave-on treatinent Control I II Raw Material (wt.?wt.) % (wt.?wt.) % (wt.?wt.) 9% Distilled Water QS QS QS Ethanol SO.OO SO.OO SO.OO Polyacrylamide & 1.85 1.85 1.85 C13-14 Isoparaffin & Laureth-7 (Sepigel 305) Perfume O46 O46 O46 Salicylic acid O 2.0 O 5-Chlorosalicylic acid O O 2.0 2,4- O O O Dihydroxybenzoic acid Oleic acid O O O 2-Hexyl-1-decanol O O O US 2016/01581 28 A1 Jun. 9, 2016

-continued Formula Example

Leave-on treatinent Control III Raw Material Final pH 4.2 4.2 4.2 4.2 4.2 4.2 % Water Reduction 4 5 5 7 versus Leave-on Treatment Control at dose of 0.10 g of composition for 1.0 g of hair % Water Reduction 9 8 10 10 versus Leave-on Treatment Control at dose of 0.50 g of composition for 1.0 g of hair. Control is dosed at 0.50 g of composition for 1.0 g of hair Feel Rating Leave-on 2 3 2 4 Treatment Control at dose of 0.10 g of composition for 1.0 g of hair

0061 (b) 5-Chlorosalicylic acid and isostearyl isostear Formula Example ate, 0062 (c) 5-Chlorosalicylic acid and 2-hexyl-1-decanol Raw Material VIII IX X XI XII XIII and isostearyl isostearate Distilled Water QS QS QS QS provide, not only water absorption reduction (resulting in Ethanol SO.O SO.O SO.O SO.O SO.O 5-Chlorosalicylic acid 1.O 1.O 1.O 1.O frizz benefit), but also tactile feel benefit. This is shown by the 2-Hexyl-1-decanol S.O S.O S.O feel comparisons of (a) Example XI versus Examples VIII Isostearyl IsoStearate 2.0 2.0 2.0 and IX, (b) Example XII versus Examples VIII and X, and (c) Final pH 4 4 4 4 Example XIII versus Examples VIII, IX and X. % Water Reduction 0.7 1.O 2.0 1.4 3.0 versus Leave-on Treatment Control at Additional Evaluations dose of 0.10 g of composition for 0063 Additional leave-on treatment compositions are 1.0 g of hair prepared (Tables 1 and 2) according to the procedure Feel Rating (on 5 2 3 3 described above, which are used to treat hair switches using scale point with 5 the procedure described above (amount of 0.10 g of compo as highest and 1 as sition per g of hair). The Switch is kept at high humidity lowest) (above 85%) for 2 hours. Then, ten experts are asked to rate each hair switch in terms of frizz, clean feel, and greasy feel, based on a 5 point Scale, 5 being the highest and 1 being the Results: lowest rating. Acceptable values are: 0059 Formula I to XIII showed 96 water reduction at high 0064. For frizz, less than 2 (lower number corresponds humidity. Higher % water reductions are observed in hair to less frizz); treated with higher doses of leave-on Formulas I-XIII 0065 For no greasy feel less than 3, (lower number The feel assessment results indicate that combinations of corresponds to less greasy feel), and 0060 (a) 5-Chlorosalicylic acid and 2-hexyl-1-de 0.066 For clean feel greater than 3 (higher number cor canol: responds to cleaner feel). TABLE 1. Class I Compounds Formula Example

Raw Material Control XIV XV XVI XVII XVIII

Distilled Water SO.0% 49.5% 49.5% 49.5% 49.5% 49.5% Ethanol SO.0% 49.5% 49.5% 49.5% 49.5% 49.5% 5-Chlorosalicylic acid US 2016/01581 28 A1 Jun. 9, 2016

TABLE 1-continued Class I Compounds Formula Example

Raw Material Control XIV XV XVI XVII XVIII

Salicylic acid O% O% 196 O% O% O% 4-Hydroxybenzenesulphonic acid O% O% O% 19-0 O% O% 2,4-Dihydroxybenzoic acid O% O% O% O% 196 O% Terminal Amino Silicone O% O% O% O% O% 190 Composition pH adjusted to 4.2 4.2 4.2 4.2 4.2 4.2 Greasy Feel 2 1 2 2 2 4 Frizz 4 2 1 2 2 3 Clean Feel 4 4 3 4 4 1

Results of Hair Switch Rating from Class I Molecules: brown hair Switches (4.0 g) are washed with clarifying sham 0067 Molecules (5-chlorosalicylic acid, salicylic acid, poo, and then treated with leave-on treatment of composition 4-hydroxybenzenesulphonic acid, 2,4-dihydroxybenzoic acid) from Class I provide hair benefits. More specifically, XXIV according to the protocol described above. Before the Table 1 shows that hair treatments with 5-chlorosalicyclic evaluation, the Switches are air dried overnight in a controlled acid, salicylic acid, 4-hydroxybenzenesulfonic acid and 2,4- temperature and humidity room (22°C./50% RH). The fric dihydroxybenzoic acid provide fizz protection with clean feel tion force (grams) between the hair Surface and aurethane pad and without greasy feel negative, as opposed to treatment with terminal aminosilicone, which provide some frizz, ben along the hair is measured, with three measurements per efit but with greasy feel negative and significantly less clean Switch using an Instron Tester instrument (Instron 5542, feel. Instron, Inc, Canton, Mass., USA). TABLE 2 Class II Compounds Formula Example

Raw Material Control XIX XX XXI XXII XXIII

Distilled Water SO.0% 49.5% 49.5% 49.5% 49.5% 49.5% Ethanol SO.0% 49.5% 49.5% 49.5% 49.5% 49.5% Isostearyl isostearate O% 196 O% O% O% O% 2-Hydroxyethyl salicylate O% O% 190 O% O% O% Octyl salicylate O% O% O% 196 O% O% 2-Hexyl-1-decanol O% O% O% O% 190 O% Terminal Amino Silicone O% O% O% O% O% 196 Composition pH adjusted to 4.2 4.2 4.2 4.2 4.2 4.2 Greasy Feel 2 2 2 2 3 4 Frizz 4 2 2 1 1 3 Clean Feel 4 3 3 3 3 1

Results of Hair Switch Rating from Class II Molecules: TABLE 3 0068 Molecules (Isostearyl isostearate, 2-hydroxylethyl salicylate, octyl salicylate, 2-hexyl-1-decanol) from Class II Hair Friction provide hair benefits. More specifically, Table 2 shows that Formula Example hair treatment with isostearyl isostearate, 2-hydroxyethyl Control Hair - salicylate, octyl salicylate, and 3-hexyl-1-decanol provide Raw Material XXIV No Treatment Distilled Water 49.5% frizZ protection with clean feel and without greasy feel nega Ethanol 49.5% tive, as opposed to treatment with terminal aminosilicone, 24 dihydroxybenzoic acid 190 Silicone oil O% which provide some frizz benefit but with greasy feel negative Composition pH adjusted to 4.2 and significantly less clean feel. Average Force (g) 40 55 Evaluation of Hair Friction As Table 3 indicates, treatment of hair with leave-on compo sition containing Moisture Control material and silicone oil 0069 Leave-on formulation containing Moisture Control results in reduced hair friction, which indicates improved dry Material and Silicone oil shows improvement in dry feel feel. compared to untreated hair. This is concluded by measure 0070. It is known that organic hydrophobic molecules that ment of dry hair friction. For this evaluation, natural virgin are naturally present inside the hair (e.g. as part of Cell Mem US 2016/01581 28 A1 Jun. 9, 2016 brane Complex lipids) contribute to its strength and integrity. The penetration amount of 5-chlorosalicylic acid is deter It is also known that cosmetic treatments, such as oxidative mined using the following protocol. Each hair tress is coloring and permanent shaping result in reduction of the extracted 3 times with 0.1% TFA (Trifluoroacetic acid) in concentration of such hydrophobic material from hair. Thus, methanol and the individual extracts are analyzed separately penetration of hydrophobic materials (e.g. Class II materials) using HPLC method. inside the hair can contribute to lipid replenishment, which, at 0072. In addition to the increase of the penetration amount the same time, reduces water uptake to deliver moisture or of the moisture control material, the presence of glycol in the frizz control benefit. Combination of different Class II mate composition prevents the crystallization of part of the mois rials e.g. benzyl alcohol, 2-hexyl-1-decanol, isostearyl isos ture control material in the surface of the hair. Such crystal tearate, have multi-functionality of penetration, getting lization causes a non-Smooth, negative hair feel, which may embedded into lipid of hair and also increasing the penetra be perceived by consumers as hair damage or lack of condi tion of other hydrophobic materials like oleic resulting in tioning. further increase hydrophobicity of the hair interior. 0073. It has been observed that in an embodiment of the present invention the presence of propylene glycol may pro Penetration of Moisture Control Material Inside the Hair vide penetration enhancement for Molecular Class I and 0071. In an embodiment of the present invention, compo Class II materials. sitions can comprise of glycols, polyglycols, urea, ethers or mixture thereof. These materials increase penetration of Conditioner Composition moisture control actives Such as salicylic acid, 5-chloro Sali cylic acid, improving their performance. Propylene glycol, 0074 The personal care composition of the present inven butylene glycol and other glycols, increase penetration of tion comprises a cationic Surfactant, high melting point fatty 5-chlorosalicylic acid inside hair as it acts as carrier for the compound, and aqueous carrier. The Surfactants, the high actives to penetrate further. As active penetration increases, melting point fatty compounds, and the aqueous carrier are in there is an increase in efficacy of the active, i.e. there is the form of emulsion. increase in % water reduction as shown below in Table 4. Table 4 shows the amount of 5-chlorosalicylic acid that pen Cationic Surfactant System etrates inside oxidatively damaged hair after hair treatment with two different compositions. It also shows the '% water 0075. The composition of the present invention comprises reduction observed after the treatment versus treatment with a cationic Surfactant system. The cationic Surfactant system can be one cationic Surfactant or a mixture of two or more control leave-on treatment compositions. These results dem cationic Surfactants. Preferably, the cationic Surfactant sys onstrate that 5-chlorosalicylic acid penetrates 4 times more in tem is selected from: mono-long alkyl quaternized ammo the presence of propylene glycol and there is an increase in 96 nium salt; a combination of mono-long alkyl quaternized water reduction as measured by DVS of approximate 4 times ammonium salt and di-long alkyl quaternized ammonium more than without propylene glycol. Another example of salt; mono-long alkyl amidoamine salt; a combination of material that enhances the penetration of moisture control mono-long alkyl amidoamine salt and di-long alkyl quater material is 2-hydroxyethyl urea. Leave on treatment compo nized ammonium salt, a combination of mono-long alkyl sition that contain 2% of 2-hydroxyethyl urea increases the amindoamine salt and mono-long alkyl quaternized ammo penetration of salicylic acid inside hair by 14% compared to nium salt the corresponding composition that does not contain 2-hy 0076. The cationic surfactant system is included in the droxyethyl urea (see example XXVII and XXVIII). composition at a level by weight of from about 0.1% to about TABLE 4 Enhancing of hair penetration of Moisture Control Material in oxidatively damaged (bleached) Caucasian hair Formula Example

Raw Material Control XXV XXVI XXVII XXVIII

Distilled Water SO.0% 48.93% 43.9% 48.93% 48.00% Ethanol SO.0% 48.93% 43.9% 48.93% 48.00% 5-Chlorosalicylic acid O.0% 2.0% 2.0% O.0% O.0% 2-hydroxyethyl urea O.0% O.0% O.0% O.0% 2.0% Salicylic acid O.0% O.0% O.0% 2.0% 2.0% 2,4-Dihydroxybenzoic acid O.0% O.15% O.15% O.0% O.0% Propylene glycol O.0% O% 10% O% O.0% Composition pH adjusted to 4.2 4.2 4.2 4.2 4.2 % Water Reduction versus control treatment O.67% 3% Amount of 5-chlorosalicylic acid inside the 1 3.97 hair (mg/g of hair) Amount of Salicylic acid inside hair (mg/g of 4.7 S.6 hair) after 5 cycles US 2016/01581 28 A1 Jun. 9, 2016

10%, preferably from about 0.5% to about 8%, more prefer hyldimethylamine, behenamidopropyldimethylamine, behe ably from about 0.8% to about 5%, still more preferably from namidopropyldiethylamine, behenamidoethyldiethylamine, about 1.0% to about 4%. behenamidoethyldimethylamine, arachidamidopropyldim ethylamine, arachidamidopropyldiethylamine, arachidami Mono-Long Alkyl Quaternized Ammonium Salt doethyldiethylamine, arachidamidoethyldimethylamine, diethylaminoethylstearamide. Useful amines in the present 0077. The monoalkyl quaternized ammonium salt cat invention are disclosed in U.S. Pat. No. 4,275,055, Nachtigal, ionic Surfactants useful herein are those having one long alkyl etal. These amines can also be used in combination with acids chain which has from 12 to 30 carbonatoms, preferably from Such as 1-glutamic acid, lactic acid, hydrochloric acid, malic 16 to 24 carbon atoms, more preferably C18-22 alkyl group. acid, Succinic acid, acetic acid, fumaric acid, tartaric acid, The remaining groups attached to nitrogen are independently citric acid, 1-glutamic hydrochloride, maleic acid, and mix selected from an alkyl group of from 1 to about 4 carbon tures thereof more preferably 1-glutamic acid, lactic acid, atoms or an alkoxy, polyoxyalkylene, alkylamido, hydroxy citric acid. The amines herein are preferably partially neutral alkyl, aryl or alkylaryl group having up to about 4 carbon ized with any of the acids at a molar ratio of the amine to the atOmS. acid of from about 1:0.3 to about 1:2, more preferably from 0078 Mono-long alkyl quaternized ammonium salts use about 1:0.4 to about 1:1. ful herein are those having the formula (I): Di-Long Alkyl Quaternized Ammonium Salt (I) 0080 Di-long alkyl quaternized ammonium salt is prefer ably combined with a mono-long alkyl quaternized ammo nium salt or mono-long alkyl amidoamine salt. It is believed that such combination can provide easy-to-rinse feel, com pared to single use of a monoalkyl quaternized ammonium salt or mono-long alkyl amidoamine salt. In such combina wherein one of R7, R7, R77 and R7 is selected from an alkyl tion with a mono-long alkyl quaternized ammonium salt or group of from 12 to 30 carbon atoms or an aromatic, alkoxy, mono-long alkyl amidoamine salt, the di-long alkyl quater polyoxyalkylene, alkylamido, hydroxyalkyl, aryl or alkylaryl nized ammonium salts are used at a level such that the wt % group having up to about 30 carbon atoms; the remainder of of the dialkyl quaternized ammonium salt in the cationic R7, R7, R77 and R7 are independently selected from an surfactant system is in the range of preferably from about alkyl group of from 1 to about 4 carbon atoms or an alkoxy, 10% to about 50%, more preferably from about 30% to about polyoxyalkylene, alkylamido, hydroxyalkyl, aryl or alkylaryl 45%. group having up to about 4 carbon atoms; and X is a salt I0081. The dialkyl quaternized ammonium salt cationic forming anion Such as those selected from halogen, (e.g. Surfactants useful herein are those having two long alkyl chloride, bromide), acetate, citrate, lactate, glycolate, phos chains having 12-30 carbon atoms, preferably 16-24 carbon phate, nitrate, Sulfonate, Sulfate, alkylsulfate, and alkyl Sul atoms, more preferably 18-22 carbon atoms. The remaining fonate radicals. The alkyl groups can contain, in addition to groups attached to nitrogen are independently selected from carbon and hydrogen atoms, ether and/or ester linkages, and an alkyl group of from 1 to about 4 carbonatoms or analkoxy, other groups such as amino groups. The longer chain alkyl polyoxyalkylene, alkylamido, hydroxyalkyl, aryl or alkylaryl groups, e.g., those of about 12 carbons, or higher, can be group having up to about 4 carbon atoms. saturated or unsaturated. Preferably, one of R. R. R77 and I0082 Di-long alkyl quaternized ammonium salts useful R’ is selected from an alkyl group of from 12 to 30 carbon herein are those having the formula (II): atoms, more preferably from 16 to 24 carbonatoms, still more preferably from 18 to 22 carbon atoms, even more preferably 22 carbon atoms; the remainder of R7, R7, R77 and Rare (II) independently selected from CH, CH, CHOH, and mix tures thereof, and X is selected from the group consisting of Cl, Br, CHOSO, CHOSO, and mixtures thereof. Non limiting examples of Such mono-long alkyl quaternized ammonium salt cationic Surfactants include: behenyl trim ethyl ammonium salt; Stearyl trimethyl ammonium salt; cetyl trimethyl ammonium salt; and hydrogenated tallow alkyl tri whereintwo of R7, R7, R77 and R7 is selected from an alkyl group of from 12 to 30 carbon atoms or an aromatic, alkoxy, methyl ammonium salt. polyoxyalkylene, alkylamido, hydroxyalkyl, aryl or alkylaryl group having up to about 30 carbon atoms; the remainder of Mono-Long Alkyl Amidoamine Salt R. R. R77 and R7 are independently selected from an 0079 Mono-long alkylamines are also suitable as cationic alkyl group of from 1 to about 4 carbon atoms or an alkoxy, Surfactants. Primary, secondary, and tertiary fatty amines are polyoxyalkylene, alkylamido, hydroxyalkyl, aryl or alkylaryl useful. Particularly useful are tertiary amido amines having group having up to about 4 carbon atoms; and X is a salt an alkyl group of from about 12 to about 22 carbons. Exem forming anion Such as those selected from halogen, (e.g. plary tertiary amido amines include: Stearamidopropyldim chloride, bromide), acetate, citrate, lactate, glycolate, phos ethylamine, Stearamidopropyldiethylamine, Stearamidoeth phate, nitrate, Sulfonate, Sulfate, alkylsulfate, and alkyl Sul yldiethylamine, Stearamidoethyldimethylamine, fonate radicals. The alkyl groups can contain, in addition to palmitamidopropyldimethylamine, palmitamidopropyldi carbon and hydrogenatoms, ether and/or ester linkages, and ethylamine, palmitamidoethyldiethylamine, palmitamidoet other groups such as amino groups. The longer chain alkyl US 2016/01581 28 A1 Jun. 9, 2016 groups, e.g., those of about 12 carbons, or higher, can be Aqueous Carrier saturated or unsaturated. Preferably, one of R7, R7, R77 and I0087. The gel matrix of the hair care composition of the R’ is selected from an alkyl group of from 12 to 30 carbon present invention includes an aqueous carrier. Accordingly, atoms, more preferably from 16 to 24 carbonatoms, still more the formulations of the present invention can be in the form of preferably from 18 to 22 carbon atoms, even more preferably pourable liquids (under ambient conditions). Such composi 22 carbon atoms; the remainder of R7, R7, R77 and Rare tions will therefore typically comprise an aqueous carrier, independently selected from CH, CH, CHOH, and mix which is present at a level of from about 20 wt.% to about 95 tures thereof, and X is selected from the group consisting of wt.%, or even from about 60 wt.% to about 85 wt.%. The Cl, Br, CHOSO, CHOSO, and mixtures thereof. Such aqueous carrier may comprise water, or a miscible mixture of dialkyl quaternized ammonium salt cationic Surfactants water and organic solvent, and in one aspect may comprise include, for example, dialkyl (14-18) dimethyl ammonium water with minimal or no significant concentrations of chloride, ditallow alkyl dimethyl ammonium chloride, dihy organic solvent, except as otherwise incidentally incorpo drogenated tallow alkyl dimethyl ammonium chloride, dis rated into the composition as minor ingredients of other com tearyl dimethyl ammonium chloride, and dicetyl dimethyl ponents. ammonium chloride. Such dialkyl quaternized ammonium I0088. The aqueous carrier useful in the present invention salt cationic Surfactants also include, for example, asymmet includes water and water solutions of lower alkyl alcohols ric dialkyl quaternized ammonium salt cationic Surfactants. and polyhydric alcohols. The lower alkyl alcohols useful herein are monohydric alcohols having 1 to 6 carbons, in one I0083 High Melting Point Fatty Compound aspect, ethanol and isopropanol. The polyhydric alcohols 0084. The high melting point fatty compound useful useful herein include propylene glycol, hexylene glycol, herein has a melting point of 40°C. or higher, and is selected glycerin, and propane diol. from the group consisting of fatty alcohols, fatty acids, fatty I0089. According to embodiments of the present invention, alcohol derivatives, fatty acid derivatives, and mixtures the hair care compositions may have a pH in the range from thereof. It is understood by the artisan that the compounds about 2 to about 10, at 25°C. In one embodiment, the hair care disclosed in this section of the specification can in some composition has a pH in the range from about 2 to about 6. instances fall into more than one classification, e.g., some which may help to solubilize minerals and redox metals fatty alcohol derivatives can also be classified as fatty acid already deposited on the hair. Thus, the hair care composition derivatives. However, a given classification is not intended to can also be effective toward washing out the existing minerals be a limitation on that particular compound, but is done so for and redox metals deposits, which can reduce cuticle distor convenience of classification and nomenclature. Further, it is tion and thereby reduce cuticle chipping and damage. understood by the artisan that, depending on the number and position of double bonds, and length and position of the Gel Matrix branches, certain compounds having certain required carbon 0090 The composition of the present invention comprises atoms may have a melting point of less than 25° C. Such agel matrix. The gel matrix comprises a cationic Surfactant, a compounds of low melting point are not intended to be high melting point fatty compound, and an aqueous carrier. included in this section. Non-limiting examples of the high 0091. The gel matrix is suitable for providing various con melting point compounds are found in International Cosmetic ditioning benefits such as slippery feel during the application Ingredient Dictionary, Fifth Edition, 1993, and CTFA Cos to wet hair and softness and moisturized feel on dry hair. In metic Ingredient Handbook, Second Edition, 1992. Among a view of providing the above gel matrix, the cationic Surfactant variety of high melting point fatty compounds, fatty alcohols and the high melting point fatty compound are contained at a are preferably used in the composition of the present inven level such that the weight ratio of the cationic surfactant to the tion. The fatty alcohols useful herein are those having from high melting point fatty compound is in the range of prefer about 14 to about 30 carbonatoms, preferably from about 16 ably from about 1:1 to about 1:10, more preferably from to about 22 carbon atoms. These fatty alcohols are saturated about 1:1 to about 1:6. and can be straight or branched-chain alcohols. Preferred fatty alcohols include, for example, cetyl alcohol, Stearyl Additional Components alcohol, behenyl alcohol, and mixtures thereof. 0085 High melting point fatty compounds of a single 0092 Silicone Conditioning Agent compound of high purity are preferred. Single compounds of 0093. The compositions of the present invention may con pure fatty alcohols selected from the group of pure cetyl tain one or more silicone conditioning agents. Examples of alcohol, Stearyl alcohol, and behenyl alcohol are highly pre the silicones include dimethicones, dimethiconols, cyclic sili ferred. By “pure herein, what is meant is that the compound cones, methylphenyl polysiloxane, and modified silicones has a purity of at least about 90%, preferably at least about with various functional groups such as amino groups, quater 95%. These single compounds of high purity provide good nary ammonium salt groups, aliphatic groups, alcohol rinsability from the hair when the consumer rinses off the groups, carboxylic acid groups, ether groups, Sugar or composition. polysaccharide groups, fluorine-modified alkyl groups, alkoxy groups, or combinations of Such groups. Such sili I0086. The high melting point fatty compound is included cones may be soluble or insoluble in the aqueous (or non in the compositionata level of from about 0.1% to about 20%, aqueous) product carrier. In the case of insoluble liquid sili preferably from about 1% to about 15%, more preferably cones, the polymer can be in an emulsified form with droplet from about 1.5% to about 8% by weight of the composition, size of about 10 nm to about 30 micrometers Other solid or in view of providing improved conditioning benefits such as semi-solid conditioning agents may be present in the compo slippery feel during the application to wet hair, softness and sition including high melting temperature fatty alcohols, moisturized feel on dry hair. acids, esters, amides or oligomers from unsaturated esters, US 2016/01581 28 A1 Jun. 9, 2016

alcohols, amides. The oligomeric esters may be the result of spacer monomers such as acrylamide, methacrylamide, alkyl oligomerization of naturally-occuring unsaturated glyceride and dialkyl acrylamides, alkyl and dialkyl methacrylamides, esters. Such solid or semi-solid conditioning agents may be alkyl acrylate, alkyl methacrylate, vinyl caprolactone, and added or present as mixtures with organic oils. vinyl pyrrolidone. Other suitable spacer monomers include 0094) Nonionic Polymers vinyl esters, vinyl alcohol (made by hydrolysis of polyvinyl 0095. The hair care composition of the present invention acetate), maleic anhydride, propylene glycol, and ethylene may also further comprise a nonionic polymer. According to glycol. Other suitable cationic polymers useful herein an embodiment, the conditioning agent for use in the hair care include, for example, cationic celluloses, cationic starches, composition of the present invention may include a polyalky and cationic guar gums. The cationic polymer can be included lene glycol polymer. For example, polyalkylene glycols hav in the hair care compositions of the present inventionata level ing a molecular weight of more than about 1000 are useful of from about 0.001 wt.% to about 10 wt.%. In one embodi herein. Useful are those having the following general formula ment, the cationic polymeris present in an amount up to about (VIII): 5 wt % based on the weight of the composition. 0101 Benefit Agents 0102. In an embodiment, the hair care composition further (VIII) comprises one or more additional benefit agents. The benefit H--OCHCH-OH agents comprise a material selected from the group consisting l of anti-dandruff agents, anti-fungal agents, anti-itch agents, anti-bacterial agents, anti-microbial agents, moisturization wherein R'' is selected from the group consisting of H, agents, anti-oxidants, vitamins, lipid soluble vitamins, methyl, and mixtures thereof; and V is the number of ethoxy chelants, perfumes, brighteners, enzymes, sensates, attracta units. The polyalkylene glycols, such as polyethylene gly nts, dyes, pigments, bleaches, and mixtures thereof. In one cols, can be included in the hair care compositions of the aspect said benefit agent may comprise an anti-dandruff present inventionata level of from about 0.001 wt.% to about agent. Such anti-dandruff particulate should be physically 10 wt.%. In an embodiment, the polyethylene glycol is and chemically compatible with the components of the com present in an amount up to about 5 wt.% based on the weight position, and should not otherwise unduly impair product of the composition. Polyethylene glycol polymers useful stability, aesthetics or performance. herein are PEG-2M (also known as Polyox WSR(R) N-10, 0103) According to an embodiment, the hair care compo which is available from Union Carbide and as PEG-2,000); sition comprises an anti-dandruff active, which may be an PEG-5M (also known as Polyox WSR(R) N-35 and Polyox anti-dandruff active particulate. In an embodiment, the anti WSRR) N-80, available from Union Carbide and as PEG-5, dandruff active is selected from the group consisting of 000 and Polyethylene Glycol 300,000); PEG-7M (also pyridinethione salts; azoles, such as ketoconazole, econazole, known as Polyox WSR(R) N-750 available from Union Car and elubiol; selenium sulphide; particulate sulfur, keratolytic bide); PEG-9M (also known as Polyox WSR(R) N-3333 avail agents such as Salicylic acid; and mixtures thereof. In an able from Union Carbide); and PEG-14 M (also known as embodiment, the anti-dandruff particulate is a pyridinethione Polyox WSR(R) N-3000 available from Union Carbide). salt. Pyridinethione particulates are suitable particulate anti 0096 Organic Conditioning Materials dandruff actives. In an embodiment, the anti-dandruff active 0097. The conditioning agent of the compositions of the is a 1-hydroxy-2-pyridinethione salt and is in particulate present invention may also comprise at least one organic form. In an embodiment, the concentration of pyridinethione conditioning material Such as oil or wax, either alone or in anti-dandruff particulate ranges from about 0.01 wt.% to combination with other conditioning agents, such as the sili about 5 wt.%, or from about 0.1 wt.% to about 3 wt.%, or cones described above. The organic material can be non from about 0.1 wt.% to about 2 wt.%. In an embodiment, the polymeric, oligomeric or polymeric. It may be in the form of pyridinethione salts are those formed from heavy metals such oil or wax and may be added in the formulation neat or in a as Zinc, tin, cadmium, magnesium, aluminium and Zirco pre-emulsified form. Some non-limiting examples of organic nium, generally Zinc, typically the Zinc salt of 1-hydroxy-2- conditioning materials include, but are not limited to: i) pyridinethione (known as “zinc pyridinethione' or “ZPT), hydrocarbon oils; ii) polyolefins, iii) fatty esters, iv) fluori commonly 1-hydroxy-2-pyridinethione salts in platelet par nated conditioning compounds, V) fatty alcohols, vi) alkyl ticle form. In an embodiment, the 1-hydroxy-2-pyridineth glucosides and alkyl glucoside derivatives; vii) quaternary ione salts in platelet particle form have an average particle ammonium compounds; viii) polyethylene glycols and size of up to about 20 microns, or up to about 5 microns, or up polypropylene glycols having a molecular weight of up to to about 2.5 microns. Salts formed from other cations, such as about 2,000,000 including those with CTFA names PEG-200, sodium, may also be suitable. Pyridinethione anti-dandruff PEG-400, PEG-600, PEG-1000, PEG-2M, PEG-7M, PEG actives are described, for example, in U.S. Pat. No. 2,809,971; 14M, PEG-45M and mixtures thereof. U.S. Pat. No. 3,236,733; U.S. Pat. No. 3,753, 196; U.S. Pat. 0098. Deposition Aids No. 3,761,418; U.S. Pat. No. 4,345,080; U.S. Pat. No. 4,323, 0099. The hair care compositions of the present invention 683: U.S. Pat. No. 4,379,753; and U.S. Pat. No. 4,470,982. may further comprise a deposition aid, such as a cationic 0104. In an embodiment, in addition to the anti-dandruff polymer. Cationic polymers useful herein are those having an active selected from polyvalent metal salts of pyrithione, the average molecular weight of at least about 5,000, alterna composition further comprises one or more anti-fungal and/ tively from about 10,000 to about 10 million, and alterna or anti-microbial actives. In an embodiment, the anti-micro tively from about 100,000 to about 2 million. bial active is selected from the group consisting of coal tar, 0100 Suitable cationic polymers include, for example, Sulfur, fcharcoal, whitfield's ointment, castellani’s paint, alu copolymers of vinyl monomers having cationic amine or minum chloride, gentian violet, octopiroX (piroctone ola quaternary ammonium functionalities with water soluble mine), ciclopiroX olamine, undecylenic acid and its metal US 2016/01581 28 A1 Jun. 9, 2016

salts, potassium permanganate, selenium Sulphide, sodium sition. Natural ZLMs can also occur wherein anionic layer thiosulfate, propylene glycol, oil of bitter orange, urea prepa species such as clay-type minerals (e.g., phyllosilicates) con rations, griseofulvin, 8-hydroxyquinoline ciloquinol, tain ion-exchanged Zinc gallery ions. All of these natural thiobendazole, thiocarbamates, haloprogin, polyenes, materials can also be obtained synthetically or formed in situ hydroxypyridone, morpholine, benzylamine, allylamines in a composition or during a production process. (such as terbinafine), tea tree oil, clove leaf oil, coriander, 0.109 Another common class of ZLMs, which are often, palmarosa, berberine, thyme red, cinnamon oil, cinnamic but not always, synthetic, is layered double hydroxides. In an aldehyde, citronellic acid, hinokitol, ichthyol pale, Sensiva embodiment, the ZLM is a layered double hydroxide con SC-50, Elestab HP-100, azelaic acid, lyticase, iodopropynyl forming to the formula M. "M" (OH), "A" inH2O butylcarbamate (IPBC), isothiazalinones such as octyl isothi wherein some or all of the divalent ions (M*) are zinc ions azalinone, and azoles, and mixtures thereof. In an embodi (Crepaldi, E. L. Pava, PC, Tronto, J. Valim, J B J. Colloid ment, the anti-microbial is selected from the group consisting Interfac. Sci. 2002, 248, 429–42). Yet another class of ZLMs of itraconazole, ketoconazole, selenium Sulphide, coal tar, can be prepared called hydroxy double salts (Morioka, H., and mixtures thereof. In an embodiment, the azole anti-mi Tagaya, H., Karasu, M. Kadokawa, J. Chiba, K Inorg. Chem. crobials is animidazole selected from the group consisting of 1999, 38, 4211-6). In an embodiment, the ZLM is a hydroxy benzimidazole, benzothiazole, bifonazole, butaconazole double salt conforming to the formula MM" (OH), nitrate, climbazole, clotrimazole, croconazole, eberconazole, (1-3)]"A" sinH2O where the two metal ions (M*) may econazole, elubiol, fenticonazole, fluconazole, flutimazole, be the same or different. If they are the same and represented isoconazole, ketoconazole, lanoconazole, metronidazole, by zinc, the formula simplifies to Zn(OH), "2XA. miconazole, neticonazole, omoconazole, oxiconazole nitrate, nHO. This latterformula represents (where x=0.4) materials Sertaconazole, Sulconazole nitrate, tioconazole, thiazole, and Such as Zinc hydroxychloride and Zinc hydroxynitrate. In an mixtures thereof, or the azole anti-microbials is a triazole embodiment, the ZLM is zinc hydroxychloride and/or Zinc selected from the group consisting of terconazole, itracona hydroxynitrate. These are related to hydrozincite as well Zole, and mixtures thereof. When present in the hair care wherein a divalent anion replace the monovalent anion. These composition, the azole anti-microbial active is included in an materials can also be formed in situ in a composition or in or amount of from about 0.01 wt.% to about 5 wt.%, or from during a production process. about 0.1 wt.% to about 3 wt.%, or from about 0.3 wt.% to 0110. In embodiments having a zinc-containing layered about 2 wt.%. In an embodiment, the azole anti-microbial material and a pyrithione or polyvalent metal salt of active is ketoconazole. In an embodiment, the sole anti-mi pyrithione, the ratio of zinc-containing layered material to crobial active is ketoconazole. pyrithione or a polyvalent metal salt of pyrithione is from 0105 Embodiments of the hair care composition may also about 5:100 to about 10:1, or from about 2:10 to about 5:1, or comprise a combination of anti-microbial actives. In an from about 1:2 to about 3:1. embodiment, the combination of anti-microbial active is selected from the group of combinations consisting of 0111. The on-scalp deposition of the anti-dandruff active octopiroX and Zinc pyrithione, pine tar and Sulfur, salicylic is at least about 1 microgram/cm. The on-scalp deposition of acid and Zinc pyrithione, Salicylic acid and elubiol, Zinc the anti-dandruff active is important in view of ensuring that pyrithione and elubiol, Zinc pyrithione and climbasole, the anti-dandruff active reaches the scalp where it is able to octopiroX and climbasole, salicylic acid and octopiroX, and perform its function. In an embodiment, the deposition of the anti-dandruff active on the scalp is at least about 1.5 micro mixtures thereof. gram/cm, or at least about 2.5 microgram/cm, or at least 0106. In an embodiment, the composition comprises an about 3 microgram/cm, or at least about 4 microgram/cm, effective amount of a zinc-containing layered material. In an or at least about 6 microgram/cm, or at least about 7 micro embodiment, the composition comprises from about 0.001 gram/cm, or at least about 8 microgram/cm, or at least about wt.% to about 10 wt.%, or from about 0.01 wt.% to about 7 8 microgram/cm, or at least about 10 microgram/cm. The wt.%, or from about 0.1 wt.% to about 5 wt.% of a zinc on-scalp deposition of the anti-dandruffactive is measured by containing layered material, by total weight of the composi having the hair of individuals washed with a composition tion. comprising an anti-dandruff active, for example a composi 0107 Zinc-containing layered materials may be those tion pursuant to the present invention, by trained a cosmeti with crystal growth primarily occurring in two dimensions. It cian according to a conventional washing protocol. The hairis is conventional to describe layer structures as not only those then parted on an area of the scalp to allow an open-ended in which all the atoms are incorporated in well-defined layers, glass cylinder to be held on the Surface while an aliquot of an but also those in which there are ions or molecules between extraction solution is added and agitated prior to recovery and the layers, called gallery ions (A. F. Wells “Structural Inor analytical determination of anti-dandruff active content by ganic Chemistry’ Clarendon Press, 1975). Zinc-containing conventional methodology, such as HPLC. layered materials (ZLMs) may have zinc incorporated in the layers and/or be components of the gallery ions. The follow O112 Carrier ing classes of ZLMS represent relatively common examples 0113. The composition of the present invention may com of the general category and are not intended to be limiting as prise an aqueous carrier. The level and species of the carrier to the broader scope of materials which fit this definition. are selected according to the compatibility with other com 0108. Many ZLMs occur naturally as minerals. In an ponents, and other desired characteristic of the product. embodiment, the ZLM is selected from the group consisting 0114. The carrier useful in the present invention includes of hydrozincite (zinc carbonate hydroxide), aurichalcite water and water solutions of lower alkyl alcohols. The lower (Zinc copper carbonate hydroxide), rosasite (copper Zinc car alkyl alcohols useful herein are monohydric alcohols having bonate hydroxide), and mixtures thereof. Related minerals 1 to 6 carbons, and in a further embodiment, ethanol and that are zinc-containing may also be included in the compo isopropanol. US 2016/01581 28 A1 Jun. 9, 2016

0115. In an embodiment of the present invention, the aque with repeat units from 10-300, in another embodiment from ous carrier is substantially water. In a further embodiment, 30-200, in a further embodiment from 40-150. Non-limiting deionized water may be used. Water from natural sources examples of this class include PEG-120-methylglucose including mineral cations can also be used, depending on the dioleate, PEG-(40 or 60) sorbitan tetraoleate, PEG-150 pen desired characteristic of the product. Generally, the compo taerythrity1 tetrastearate, PEG-55 propylene glycol oleate, sitions of the present invention comprise from about 0% to PEG-150 distearate. about 99%, in an embodiment from about 50% to about 95%, I0123. In a further embodiment, the rheology modifier may in a further embodiment from about 70% to about 90%, and in be cellulose and derivatives; nonlimiting examples include a further embodiment from about 80% to about 90% water. microcrystalline cellulose, carboxymethylcelluloses, 0116 Rheology Modifier/Suspending Agents hydroxyethylcellulose, hydroxypropylcellulose, hydrox 0117. In one embodiment, the rinse-off conditioner com ypropylmethylcellulose, methylcellulose, ethylcellulose, position comprises a rheology modifier. The rheology modi nitro cellulose, cellulose sulfate, cellulose powder, and fier increases the substantivity and stability of the composi hydrophobically modified celluloses tion, improve feel and consumer's use experience (e.g. non 0.124. In an embodiment, the rheology modifier may be a dripping, spreadability, etc). Any Suitable rheology modifier guar and guar derivatives; nonlimiting examples include can be used. In an embodiment, the hair care composition hydroxypropyl guar, and hydroxypropyl guar hydroxypropyl may comprise from about 0.05% to about 10% of a rheology trimonium chloride. In an embodiment, the rheology modifier modifier, in a further embodiment, from about 0.1% to about may be polyethylene oxide, polypropylene oxide, and 10% of a rheology modifier, in yet a further embodiment, 0.125 POE-PPO copolymers. from about 0.5% to about 2% of a rheology modifier, in a I0126. In an embodiment, the rheology modifier may be further embodiment, from about 0.7% to about 2% of a rhe polyvinylpyrrolidone, crosslinked polyvinylpyrrolidone and ology modifier, and in a further embodiment from about 1% derivatives. In a further embodiment, the rheology modifier to about 1.5% of a rheology modifier. In an embodiment, the may be polyvinyalcohol and derivatives. rheology modifier may be a polyacrylamide thickener. In an I0127. In a further embodiment, the rheology modifier may embodiment, the rheology modifier may be a polymeric rhe be polyethyleneimine and derivatives. ology modifier. I0128. In another embodiment, the rheology modifier may 0118. In one embodiment, the rinse-off conditioner com be silicas; nonlimiting examples include fumed silica, pre position may comprise rheology modifiers that are cipitated silica, and silicone-surface treated silica. homopolymers based on acrylic acid, methacrylic acid or 0129. In an embodiment, the rheology modifier may be other related derivatives, non-limiting examples include water-swellable clays non-limiting examples include lapo polyacrylate, polymethacrylate, polyethylacrylate, and poly nite, bentolite, montmorilonite, Smectite, and hectonite. acrylamide. 0.130. In an embodiment, the rheology modifier may be 0119. In another embodiment, the rheology modifiers may gums nonlimiting examples include Xanthan gum, guar gum, be alkali swellable and hydrophobically-modified alkali hydroxypropyl guar gum, Arabia gum, tragacanth, galactan, Swellable acrylic copolymers or methacrylate copolymers carob gum, karayagum, and locust bean gum. non-limiting examples include acrylic acid/acrylonitrogen I0131. In a further embodiment, the rheology modifier may copolymer, acrylates/steareth-20 itaconate copolymer, acry be, dibenzylidene Sorbitol, karaggenan, pectin, agar, quince lates/ceteth-20 itaconate copolymer, acrylates/aminoacry seed (Cydonia Oblonga Mill), starch (from rice, corn, potato, lates copolymer, acrylates/steareth-20 methacrylate copoly wheat, etc), starch-derivatives (e.g. carboxymethyl starch, mer, acrylates/beheneth-25 methacrylate copolymer, methylhydroxypropyl Starch), algae extracts, dextran, Succi acrylates/steareth-20 methacrylate crosspolymer, acrylates/ noglucan, and pulleran. vinylneodecanoate crosspolymer, and acrylates/C10-C30 0.132. In an embodiment, the composition of the present alkyl acrylate crosspolymer. invention may comprise Suspending agents including crystal 0120 In a further embodiment, the rheology modifiers line Suspending agents which can be categorized as acyl may be crosslinked acrylic polymers, a non-limiting example derivatives, long chain amine oxides, and mixtures thereof. includes carbomers. These suspending agents are described in U.S. Pat. No. 4,741, 0121. In a father embodiment, the rheology modifiers may 855. These Suspending agents include ethylene glycol esters be alginic acid-based materials; non-limiting examples offatty acids in one aspect having from about 16 to about 22 include Sodium alginate, and alginic acid propylene glycol carbon atoms. In one aspect, useful Suspending agents esterS. include ethylene glycol Stearates, both mono and distearate, 0122. In a further embodiment, the rheology modifier may but in one aspect, the distearate containing less than about 7% be an associative polymeric thickeners, non-limiting of the mono Stearate. Other Suitable Suspending agents examples include: Hydrophobically modified cellulose include alkanolamides offatty acids, having from about 16 to derivatives; Hydrophobically modified alkoxylated urethane about 22 carbonatoms, or even about 16 to 18 carbonatoms, polymers, nonlimiting example include PEG-150/decyl alco examples of which include Stearic monoethanolamide, hol/SMDI copolymer, PEG-150/stearyl alcohol/SMDI Stearic diethanolamide, Stearic monoisopropanolamide and copolymer, polyurethane-39; Hydrophobically modified, Stearic monoethanolamide Stearate. Other long chain acyl alkali Swellable emulsions, non-limiting examples include derivatives include long chain esters of long chain fatty acids hydrophobically modified polyacrylates, hydrophobically (e.g., Stearyl Stearate, cetyl palmitate, etc.); long chain esters modified polyacrylic acids, and hydrophobically modified of long chain alkanol amides (e.g., Stearamide diethanola polyacrylamides; hydrophobically modified polyethers mide distearate, Stearamide monoethanolamide Stearate); and wherein these materials may have a hydrophobe that can be glyceryl esters (e.g., glyceryl distearate, trihydroxy Stearin, selected from cetyl, Stearyl, oleayl, and combinations thereof, tribehenin) a commercial example of which is Thixin R. R and a hydrophilic portion of repeating ethylene oxide groups available from Rheox, Inc. Long chain acyl derivatives, eth US 2016/01581 28 A1 Jun. 9, 2016 ylene glycol esters of long chain carboxylic acids, long chain stantially' is utilized herein to represent the inherent degree amine oxides, and alkanol amides of long chain carboxylic ofuncertainty that may be attributed to any quantitative com acids in addition to the materials listed above may be used as parison, value, measurement, or other representation. The Suspending agents. Other long chain acyl derivatives Suitable term “substantially is also utilized herein to represent the for use as Suspending agents include N.N-dihydrocarbyl degree by which a quantitative representation may vary from amido benzoic acid and soluble salts thereof (e.g., Na, K). a stated reference without resulting in a change in the basic particularly N,N-di(hydrogenated) C16, C18 and tallow function of the Subject matter at issue. amidobenzoic acid species of this family, which are commer 0.136 Having described the invention in detail and by ref cially available from Stepan Company (Northfield, Ill., erence to specific embodiments thereof, it will be apparent USA). Examples of suitable long chain amine oxides for use that modifications and variations are possible without depart as Suspending agents include alkyl dimethyl amine oxides, ing from the scope of the invention defined in the appended e.g., Stearyl dimethylamine oxide. Other Suitable Suspending claims. More specifically, although some aspects of the agents include primary amines having a fatty alkyl moiety present invention are identified herein as preferred or particu having at least about 16 carbon atoms, examples of which larly advantageous, it is contemplated that the present inven include palmitamine or Stearamine, and secondary amines tion is not necessarily limited to these preferred aspects of the having two fatty alkyl moieties each having at least about 12 invention. carbon atoms, examples of which include dipalmitoylamine 0.137 All documents cited in the Detailed Description of or di(hydrogenated tallow)amine. Still other suitable sus the Invention are, in relevant part, incorporated herein by pending agents include di(hydrogenated tallow)phthalic acid reference; the citation of any document is not to be construed amide, and crosslinked maleic anhydride-methyl vinyl ether as an admission that it is prior art with respect to the present copolymer. invention. To the extent that any meaning or definition of a 0133. Non-limiting examples of rheology modifiers term in this written document conflicts with any meaning or include acrylamide?ammonium acrylate copolymer (and) definition of the term in a document incorporated by refer polyisobutene (and) polysorbate 20, acrylamide/sodium ence, the meaning or definition assigned to the term in this acryloyldimethyl taurate copolymer/isohexadecane/polysor written document shall govern. bate 80, acrylates copolymer; acrylates/beheneth-25 meth acrylate copolymer, acrylates/C10-C30 alkyl acrylate cross What is claimed is: polymer, acrylates/steareth-20 itaconate copolymer, 1) A rinse-off conditioner composition for hair fizz reduc ammonium polyacrylate/Isohexadecane/PEG-40 castor oil, tion comprising: C12-16 alkyl PEG-2 hydroxypropylhydroxyethyl ethylcellu from about 0.2% to about 20% of a moisture control mate lose (HM-EHEC), carbomer, crosslinked polyvinylpyrroli rial or mixture of moisture control materials wherein the done (PVP), dibenzylidene sorbitol, hydroxyethyl ethylcel moisture control material is selected from one or more of lulose (EHEC), hydroxypropyl methylcellulose (HPMC), the following: hydroxypropyl methylcellulose (HPMC), hydroxypropylcel lulose (HPC), methylcellulose (MC), methylhydroxyethyl cellulose (MEHEC), PEG-150/decyl alcohol/SMDI copoly R mer, PEG-150/stearyl alcohol/SMDI copolymer, polyacryla mide/C13-14 isoparaffin/laureth-7: polyacrylate 13/poly Rs R isobutene/polysorbate 20; polyacrylate crosspolymer-6, polyamide-3; polyduaternium-37 (and) hydrogenated poly decene (and) trideceth-6, polyurethane-39, sodium acrylate/ R4 R acryloyldimethyltaurate/dimethylacrylamide, crosspolymer R3 (and) isohexadecane (and) polysorbate 60; Sodium polyacry late. Exemplary commercially-available rheology modifiers include ACULYNTM 28, KlucelTM M CS, KlucelTM H CS, wherein R is -COOY, sulfonic acid, or C=CH-COOY, KlucelTM G CS, SYLVACLEARTM AF1900V, SYLVA Y is hydrogen or a metal ion, R. R. R. R. Rs is CLEARTM PA1200V, Benece?TM E10M, BenecelTM K35M, hydrogen, methyl, ethyl, propyl, vinyl, allyl, methoxy, OptasenseTM RMC70, ACULYNTM33, ACULYNTM46, ACU ethoxy, hydroxyl, halogen, Sulfate, Sulfonate, nitro, or LYNTM22, ACULYNTM44, Carbopol UltrezTM 20, Carbopol —CH=CH-COOR, and wherein the moisture control UltrezTM 21, Carbopol UltrezTM 10, Carbopol UlterezTM30, material is an acidic material and further wherein the CarbopolTM 1342, CarbopolTM 934, CarbopolTM 940, Car moisture control material has a % Proteinbinding higher bopolTM 950, CarbopolTM 980, and CarbopolTM 981, than 20 and Molecular Volume lower than 500 and Par AcrysolTM 22, SepigelTM 305, SimulgelTM600, Sepimax Zen, tition coefficient octanol to water (log P) lower than 3 and combinations thereof. and hydrogenbinding higher than 10 and pKa lower than 0134. It is further noted that terms like “alternatively.” 5.0; and at least about a 4% frizz reduction vs. a control “usually”, “generally.” “commonly, and “typically' are not composition without the moisture control material. utilized hereinto limit the scope of the claimed invention or to 2) A rinse-off conditioner composition according to claim imply that certain features are critical, essential, or even 1 wherein the concentration of the Moisture Control Material important to the structure or function of the claimed inven or the concentration of the mixture of Moisture Control Mate tion. Rather, these terms are merely intended to highlight rial is from about 0.5% to about 8%. alternative or additional features that may or may not be 3) A rinse-off conditioner composition according to claim utilized in a particular embodiment of the present invention. 1 wherein the concentration of the Moisture Control Material 0135 For the purposes of describing and defining the or the concentration of the mixture of Moisture Control Mate present invention it is additionally noted that the term “sub rial is from about 0.5% to about 5%. US 2016/01581 28 A1 Jun. 9, 2016

4) A rinse-off conditioner composition according to claim 13) A composition according to claim 1 comprising sali 1 wherein there is a 15% frizz reduction vs. control compo cylic acid in combination with 2-hydroxyethyl urea. sition without the moisture control material. 14) A composition according to claim 13 comprising sali 5) A rinse-off conditioner composition according to claim cylic acid from about 0.5% to about 2% in combination with 1 wherein there is a 20% frizz reduction vs. control compo 2-hydroxyethyl urea from about 0.2% to about 10%. sition without the moisture control material. 15) A rinse-off conditioner composition according to claim 6) A rinse-off conditioner composition according to claim 1 wherein the pH is in the range of about 2 to about 7. 1 wherein the polar, acidic material are selected from the 16) A rinse-off conditioner composition according to claim group consisting of 2,4-dihydroxybenzoic acid, 3-hydroxy 1 wherein the pH is in the range of about 2 to about 5. benzoic acid, gallic acid, 3-aminobenzoic acid, 4-aminoben 17) A rinse-off conditioner composition according to claim Zoic acid, 2,5-dihydroxybenzoic acid, 3,4-dihydroxybenzoic 1 wherein the composition further comprises a silicone. acid,3,5-dihydroxybenzoic acid, 2,6-dihydroxybenzoic acid, 18) A rinse-off conditioner composition according to claim 5-chlorosalicylic acid, Salicylic acid, trans-ferulic acid, 1 wherein the composition further comprises materials p-coumaric acid, 4-hydroxybenezesulphonic acid, 3-chloro selected from the group consisting of conditioning materials, 4-hydroxybenzoic acid, 3.5-hydroxybenzoic acid and 2.5- organic conditioning materials, solvents, rheology modifier, dihydroxyterepthalic acid and mixtures thereof. Suspending agent, thickeners, hair health actives, anti-dan 7) A rinse-off conditioner composition according to claim druff actives, anti-oxidants, pigments, abrasives, absorbents, 6 wherein the moisture control material is selected from the biological actives, buffering agents, chelating agents, opaci group consisting of salicylic acid, 5-chlorosalicylic acid, 2,4- fying agents, pH adjusters, vitamins, chelants, perfumes, dihydrobenzoic acid, and mixtures thereof. brighteners, enzymes, sensates, attractants, anti-bacterial 8) A rinse-off conditioner composition according to claim agents, dyes, bleaches and mixtures thereof. 6 wherein the moisture control material is a combination of 19) A rinse-off conditioner composition according to claim 5-chlorosalicylic acid and 2,4-dihydrobenzoic acid. 1 wherein the composition further comprises a cationic Sur 9) A rinse-off conditioner composition according to claim factant system. 1 comprising 5-chlorosalicylic acid in combination with 2,4- 20) A rinse-off conditioner composition according to claim dihydrobenzoic acid. 1 wherein the conditioner composition further comprises: 10) A rinse-off conditioner composition according to claim i. from about 0.1% to about 20% of one or more high 1 comprising salicylic acid in combination with 2,4-dihy melting point fatty compounds, by weight of said hair drobenzoic acid. care composition; 11) A rinse-off conditioner composition according to claim 1 comprising 5-chlorosalicylic acid in combination with 2,4- ii. from about 0.1% to about 10% a cationic surfactant dihydrobenzoic acid, and propylene glycol. system of, by weight of said hair care composition; and 12) A rinse-off conditioner composition according to claim at least about 20% of an aqueous carrier, by weight of said 1 comprising 5-chlorosalicylic acid in combination with 2,4- hair care composition. dihydrobenzoic acid, and silicone. k k k k k