MXPA00001565A - Hair conditioner and 2-in-1 conditioning shampoo - Google Patents

Abstract

A 2-in-1 conditioning shampoo includes an anionic surfactant and a cationic hair conditioning agent. The cationic hair conditioning agent is a fatty aliphatic quaternary ammonium compound having ester linkages. The cationic hair conditioning agent can be prepared by reacting an alkanol amine with a fatty acid or fatty acid ester having an aliphatic group of from about 11 to about 23 carbon atoms and thereafter quaternizing the resulting esteramine with an alkylating agent.

Description

BACKGROUND Q6 THE INVENTION CAMPO TEOMJCO The present disclosure relates to hair conditioners and 2-in-1 conditioning shampoos.

BACKGROUND OF THE RELATED F € CWCA Hair conditioners are widely known and used to impart desirable attributes to human hair. For example, hair treated with conditioners is considerably softer to the touch. Additionally, hair conditioners make it more rinseable and impart greater ease to unravel and greater malleability for combing, brushing and styling. The canonical surfactants and quaternary ammonium compounds have been used in personal care products to improve the appearance, feel and health of treated hair. Cationic surfactants are those in which the activity of the surfactant resides in the positively charged cation portion of the molecule. Agents > Cationic surfactants are therefore attracted to their negatively charged film and, due to relatively low solubility and high molecular weight, they are controlled thermodynamically to remove the accusative environment of the shampoo and deposit in the hair. . Said characteristics make the cationic surfactants such as the quaternary ammonium compounds particularly suitable for the. treatment of human hair. In this way, several hair conditioning products are based on the quaternary ammonium compounds. Such compounds may have one, two or three long chain alkyl groups attached to the nitrogen head group. Typically, the long chain alkyl groups comprise chain lengths of from about 2 to about 24 carbon atoms. The ability to soften the hair and reduce the buildup of reduced static charge is typically a function of the length of the carbon atom chain and the number of chains attached to the nitrogen head group. Generally, the longer the carbon chain and the greater the number of chains, the greater the lubricity of the shampoo and the neutralization of static charge. However, the change in "coupling" of the hair and the acquisition of a heavy and greasy appearance also increases. Hair conditioners have often separated from the shampoo. However, the desire of the consumer for the convenience of personal care products for the hair that have the li mi i? ? ITT TMiMÉÉí lili] | g ^^ | Cleaning and conditioning functions in the same product has increased. These products are known as 2-in-1 conditioning shampoos. These contain cleaning and conditioning surfactants. These conditioning shampoos clean 5 dirty hair and leave a conditioner on the hair at the same time. In this way, it is necessary for the consumer to subsequently use a conditioner after using the shampoo. However, cleaning surfactants are typically anionic, ie, the activity of the surfactant resides in the anion negatively charged. Anionic and cationic surfactants are usually incompatible, forming a complex that precipitates from the solution when mixed. It is important that the correct surfactants are used to avoid interference between negatively charged cleaning surfactants and surfactants conditioning positively charged. One way of achieving this is by selecting the cationic surfactant, so that the positively charged quaternized nitrogen is sufficiently protected against the negatively charged surfactants in starting materials present in the the conditioning shampoo mixture. The foregoing can be done by the use of quaternary trialkylammonium compounds. Such compounds are known in the art but are difficult to produce and require large amounts of energy and time. In addition, these are Iti ti - tMik '- \ mrmt- * t ?? ** - * - degrade relatively slowly? I laughed at the environment. A formulation is required that provides an effective biodegradable conditioner in a minimal cleaning shampoo. EP-A-0 636 356, for example, refers to conditioning compositions for hair. The use of particular amines or quaternary ammonium compounds is described, optionally together with a silicon compound. There is no suggestion or description about how to make the 2-in-1 shampoos with the hair conditioning compositions. WO 92/10163 discloses 2 in 1 shampoo compositions. The compositions should comprise a silicon fluid component, which is unwanted.

BRIEF DESCRIPTION OF THE INVENTION Hair conditioning compositions and 2-in-1 conditioning shampoos are provided herein, which comprise: a) a conditioning agent for the hair of the formula wherein X- is an anion, R ^ R2, R3 may be the same or different and are independently straight or branched chain aikylene groups of 2 to about 6 carbon atoms; R4 is a saturated or unsaturated straight or branched chain aliphatic group having from about 1 to about 6 carbon atoms optionally substituted with hydroxy, epoxy or halogen and Ei, E2 and E3 may be the same or different in each case and are selected from the group consisting of -H, -OH and aliphatic ester groups of the following formula (II): wherein R5 is a straight or branched chain saturated or unsaturated aliphatic group of about 11 to about 23 carbon atoms, optionally substituted with hydroxy, epoxy or halogen, with the proviso that at least one of Ei, E2 or E3 is a group of the formula (II), the cationic surfactant being present in the composition in an amount not exceeding about 4% by weight; and b) an anionic surfactant or a combination of anionic / nonionic surfactant. The present formulations are superior to cleaning and conditioning shampoo compositions in which the conditioning surfactant is a trialkylammonium quaternary compound, and provides the improved dry combing capability as well as * »* ^ An accumulation of static charge P? Dücida. In addition, the hair conditioning agents of the present formulations can be used effectively in concentrations significantly below what is considered the minimum practical amount.

DETAILED DESCRIPTION OF THE PREFERRED MODALITIES The hair conditioner and the 2-in-1 conditioning shampoos according to the present disclosure contain, among other things, a hair conditioning agent of cationic surfactant having aliphatic ester groups. The present formulations provide a highly efficient use of the cationic surfactant for hair conditioning. In general, the conditioning shampoo formulation described herein contains an aqueous solution of one or more anionic surfactants, one or more cationic surfactants and, optionally, various builders and modifying ingredients. The cationic surfactant used as conditioning agent for hair in the present formulation has the formula: wherein: X- is an anion (eg, selected from chloride, bromide, iodide, nitrate, nitrite, methyl sulfate, methyl sulfate, methyl phosphate, acetate, etc.); Ri, R2 and R3 may be the same or different and are independently straight or branched chain alkylene groups of from about 2 to about 6 carbon atoms (eg, ethyl, propyl, isopropyl, butyl, sec-butyl, ter- butyl, pentyl, methylpentyl, hexyl, etc.); R4 is a saturated or unsaturated, straight or branched chain aliphatic group having from 1 to about 6 carbon atoms optionally substituted with hydroxy, epoxy, or halogen; and Ei, E2 and E3 may be the same or different in each case and are selected from the group consisting of -H, OH, and aliphatic ester groups of the formula (II): OR II -O-C-Rg (ll) wherein R5 is a straight or branched chain saturated or unsaturated aliphatic group of about 11 to about 23 carbon atoms, optionally substituted with hydroxy, epoxy, or halogen with the proviso that at least one of Ei, E2 and E3 is a group of the formula (II). The above cationic surfactant, a quaternary ammonium compound, is advantageously prepared by the reaction of a trialkanolamine with a fatty acid or fatty acid ester to provide a steramine and subsequently reacting the esteramine with an alkylating agent to provide the ammonium compound quaternary. The alkanolamine is typically selected from a group of alkanolamines, so that there is a hydroxyl function per alkyl group attached to the nitrogen. In this way, alkanolamine contains three hydroxyl functions per molecule. Suitable alkanolamines include triethanolamine ("TEA"), dietanolisopropanolamine, ethanoldiisopropanolamine, diethanolbutanolamine, ethanoldibutanolamine, triisopropanolamine, ethanol-di-n-propanolamine, diethanol-n-propanolamine, and the like. The aliphatic chain of the fatty acid / ester reactions can vary in length from about 11 to about 23 carbon atoms and can be straight or branched. The aliphatic chains may be totally saturated or may contain some unsaturation. Although the unsaturation can lead to an improvement in the yield of the properties and benefits of the formulation, the unsaturated molecules can also have a tendency to oxidize, thus affected in color and the odor stability of the shampoo composition. However, the stability of the compositions containing unsaturated components can be improved by careful manufacturing techniques and by the use of stabilizers such as antioxidants (e.g., BHT) and sequestrants (e.g., EDTA) in the starting materials, products , cationic surfactant and / or final formulation. Although it is not necessary that three aliphatic chains are identical, this is advantageous since the identical aliphatic chains can more easily achieve the compatibility of the cationic surfactant component with other components of the final shampoo / conditioner formulation. The three types of fatty acid / ester suitable for preparing intermediate esteramine herein include stearic acid, lauric acid, oleic acid, myristic acid, behemic acid, erucic acid, palmitic acid, linoleic acid and lower alkyl esters of said fatty acids , and mixtures thereof. The fatty acids can be a mixture of fatty acids such as those derived from bait, soybean, palm tree, canola, rapeseed, coconut, or other natural sources. The reaction between the alkanolamine and the fatty acid / ester is carried out in the presence of an acid catalyst such as hyposphosphoric acid at a molar ratio of fatty acid / ester to alkanolamine of from about 1.5: 1 to about 3.0: 1. , preferably from about 2.4: 1 to about 3.0: 1 and more preferably from about 2.8: 1 to about 3.0: 1. Preferably, R17 R2 and R3 are each - (CH2) 2-, R5 is C15 alkyl, and X- is methyl sulfate. Said preferred cationic surfactant can be produced by the reaction of a C16 fatty acid and triethanolamine ("TEA") in a fatty acid to TEA ratio preferably of about 3: 1. The resulting esteramine is then reacted with dimethyl sulfate to form the quaternary ammonium salt.

The reaction conditions above will make a reaction product containing a mixture of cationic monoester, diester and triester surfactant components. Particularly useful cationic surfactant compositions contain more than about 50% by weight of the triester compound, preferably more than about 60% and more preferably more than about 75% triester. The triester content may be less than about 30% by weight of the reaction product, preferably less than about 25%, and more preferably less than about 20% by weight of the reaction product. The monoester may constitute less than about 7% by weight of the reaction product. Preferably, the reaction product contains less than about 5% monoester, and more preferably the monoester constitutes less than about 5% monoester, and more preferably the monoester constitutes less than about 3% by weight of the reaction product . Surprisingly, the cationic surfactant in the conditioning shampoo formulation is effective in an amount not exceeding 4% by weight of the formulation; preferably not exceeding 3% of the formulation; preferably not exceeding 3% by weight of the formulation and more preferably not exceeding 2% by weight of the formulation. As mentioned above, the conditioning shampoo formulation of the present invention includes an anionic surfactant. Suitable anionic surfactants that provide a cleaning function in the present formulation include lauryl sulfate It is ammonium, laureth sulfate (for example, ethoxylated lauryl alcohol) of ammonium, sodium lauryl sulfate, and sodium laureth sulfate. Ammonium lauryl sulfate is preferred. It is also contemplated that the mixture of anionic and nonionic surfactants may be employed in the formulation of the current conditioning shampoos. Suitable nonionic surfactants are described in the U.S.A. No. 3,632,396, the disclosure of which is incorporated herein by reference. The shampoo and conditioner formulation may optionally also include inorganic builders such as sodium phosphate and disodium phosphate; viscosity control agents such as sodium chloride; hydrotropes such as ammonium, sodium or potassium salts of xylene sulfonates or eumeno to increase the solubility of less soluble ingredients; chelating agent such as sodium salts of ethylenediamine tetraacetic acid ("EDTA"), particularly disodium EDTA; foam impellers such as cocamide MEA (MEA = monoethanolamine mixture), cocamide DEA (DEA = diethanolamine mixture), soyamide DEA, lauramine DEA, oleamide MIPA (MIPA = isopropanolamide mixture), stearamide MEA, MEA of myristamide, MEA of lauramide, DEA of capramide, DEA of ricinoamide, DEA of myristamide, DEA of esteramide, DEA of oleylamide, DEA of ceboamide, MIPA of lauramide, MEA of ceboamide, DEA of soesteramide, and combinations thereof.; preservatives such as 5-chloro-2-methyl-4-isothiazolyl-3-one and 2-methyl-4-isothiazolyl-3-one (available as a mixture under the designation KATHON®); fatty alcohol components such as citric and steriaryl alcohols; silicone conditioners such as dimethicone and fragrance. Additionally, other optional components may be added to the conditioning shampoo composition of the present invention, so long as the basic properties of the composition are not adversely affected. Such optional components may include nonionic surfactants such as polyol and sugar esters, fatty acid alkanolamide, polyethylene glycols, ethoxylated or propoxylated alkylgens, ethoxylated or propoxylated fatty alcohols and condensation products of ethylene oxide with long chain amines; amphoteric surfactants such as cocamidopropylbetaine, lauramidepropylbetaine, coco-oleamidopropylbetaine, cocobetaine, oleylbetaine, cocamidopropylhydroxylsultaine, and dihydroxyethyl ketalglycinate; dyes and dyes for hair; opacifying and pearlizing agents such as those described in the U.S.A. 5,384,114; medicaments including antidandruff agents such as salicylic acid, elemental sulfur, selenium sulfide, zinc pyrithione, 1-hydroxypyridone and undecylenic acid; acids; alkalis; pH regulators; water softeners; thickeners, and the like.

EXAMPLE 1 The cationic surfactant for use in conditioning shampoo is prepared as follows: In a first step, 428 grams (1.67 moles) of fused palmitic acid, 0.42 grams of BHT (butylated hydroxytoluene) 0.42 grams of BHA (butylated hydroxyamide) and 0.75 grams of 50% of a solution of hydrophophoric acid were charged to a reaction vessel which was connected to an inverted stirrer, Snyder three-ball column, addition funnel, distillation equipment, nitrogen sparger and a temperature control. The mixture was maintained at about 70 ° C under nitrogen and 90.6 grams (0.61 moles) of triethanolamine (TEA) were added. After the addition of TEA, the temperature of the reaction mixture gradually increased at the rate of about 1.7 ° C per minute. When the temperature reached 105 ° C, it was emptied to reduce the pressure of the system to 0.88 bar. The heating was continued until the temperature rose to about 195 ° C. The mixture was maintained at this temperature and pressure until a desired level of diesteramine and triesteramine was produced. In a second step, a reaction vessel was fixed with temperature control, stirrer, condenser, nitrogen scavenger and addition funnel. 425 grams (0.52 moles) of the esteramide from step 1 were added to the reaction vessel together with 48.5 grams of sopropanol. Said mixture was heated to about 55 ° C under nitrogen. 61.7 grams (0.49 moles) of dimethisulfate were added by dripping at such a rate that the temperature did not exceed 85 ° C. The reaction was continued for two hours. Then 0.84 grams of 40% EDTA solution (ethylenediamine tetraacetic acid) were added and 18.5 grams of isopropanol were added. In this way, a trialkylmethyl quaternary compound was produced.

EXAMPLE II The conditioning shampoo composition was formulated using the cationic surfactant of Example 1 as follows: A first mixing component was formed by mixing 45 parts of water, 38 parts of 30% ammonium lauryl sulfate solution, and 2 parts of ammonium xylene sulfonate and the mixture was heated to about 70 ° C for a certain time to ensure adequate mixing. A second mixing component was formed separately by mixing two parts of cocamide MEA, 2 parts of cetyl alcohol, one part of ethereal alcohol, 2 parts of dimethicone, and 1.8 parts of the preferred cationic surfactant mentioned above. The mixture was heated to a temperature sufficient to liquefy the ingredients and then the second mixing component was added to the first mixing component with moderate agitation. A third mixing component was produced separately by heating 5 parts of water to 50 ° C and adding 0.2 parts of disodium thereto, 0. 3 parts of sodium phosphate, 0.01 part of disodium EDTA and 0.2 part of sodium chloride. The ingredients of the third mixing component were mixed with stirring until dissolved. Then the third blending component was added to the mixture of the first and second mixing components. With continuous agitation, the combined mixing components were cooled to less than 40 ° C to form the conditioning shampoo.

Optionally, preservatives and fragrances can be added as desired. The cationic surfactant described herein provides superior conditioning results for the hair when compared to quaternary alkylammonium surfactants such as tricetylmethylammonium chloride (currently available from Akxo Nobel, Inc., of Dobbs Ferry, New York under the designation Arquad® 316) even at concentrations below 2%. For example, when compared to a shampoo containing Arquad® 316 conditioner in the same percentage, the preferred shampoo composition described above with the preferred surfactant provides superior dry styling ability together with about 10% to 15% reduction in voltage in accumulation of static caga. Although the above description contains several specifications, said specifications should not be considered as limitations on the scope of the invention, but merely exemplifications of preferred embodiments thereof. Those skilled in the art will consider many other possible variations that are within the scope and spirit of the invention as defined by the claims appended hereto.

Claims (8)

NOVELTY OF THE INVENTION CLAIMS

1. - A hair conditioning composition comprising: a hair conditioning agent containing at least one compound of the formula where: X- is an anion; RL R2, and R3 may be the same or different and are independently straight or branched chain alkylene groups of 2 to 6 carbon atoms, R4 is a straight or branched chain saturated or unsaturated aliphatic group of 1 to 6 carbon atoms , optionally substituted with hydroxy, epoxy or halogen; and E-i, E2 and E3 may be the same or different in each case and are selected from the group consisting of -H, -OH and aliphatic ester groups of the following formula (II):

O - O-C-Rg (II) wherein R5 is a saturated or unsaturated, straight or branched chain aliphatic group of 11 to 23 carbon atoms optionally substituted with hydroxy, epoxy or halogen, the hair conditioning agent includes at least 50% by weight of a compound of formula (I) where each

E2, and E3 is a group of formula (II), the cationic surfactant being present in the composition in an amount not exceeding 4% by weight; and, b) an anionic surfactant. 2. The composition according to claim 1, further characterized in that said anion is selected from the group consisting of chloride, bromide, iodide, nitrite, nitrate, methyl sulfate, ethyl sulfate, methyl phosphate and acetate. 3. The composition according to claim 1, further characterized in that the hair conditioning agent includes: at least 75 weight percent of a compound of formula (I) wherein each Ei, E2 and E3 is individually selected from the groups of formula (II); not more than 25% by weight of a compound of formula (I) wherein two of the E-i, E2 and E3 are selected individually from the groups of formula (II); and not more than 2% by weight of a compound of formula (I) wherein only one of EL E2 or E3 is a group of formula (II).

4. The composition according to claim 1, further characterized in that the anionic surfactant is selected from the group consisting of ammonium lauryl sulfate, ammonium laureth sulfate, sodium lauryl sulfate and sodium laureth sulfate.

5. The composition according to claim 1, further characterized in that it comprises a nonionic surfactant.

6. - A method for making a conditioning agent for hair comprising the steps of: a) reacting an alkanolamine with a fatty compound to form a reaction product, the fatty compound having an aliphatic group of 11 to 23 carbon atoms and being selected from the group consisting of fatty acid and fatty acid ester, wherein the molar ratio of fatty compound to alkanolamine is in the range of 1.5: 1 to 3.0: 1; and b) reacting the reaction product of step a) with an alkylating agent to form a reaction product containing quaternary ammonium derivatives of mono-, di- and tri-esteramines, at least 50 percent by weight of the total product weight of reaction being the quaternary ammonium derivative of triesteramine.

7. The method according to claim 7, further characterized in that the reaction step of alkanolamine with the fatty compound is carried out by heating a mixture of alkanolamine and fatty compound in the presence of hydrophophoric acid.

8. A 2 in 1 conditioning shampoo comprising the hair conditioning composition according to any of claims 1-5.