Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/34—Alcohols
  • A61K8/345—Alcohols containing more than one hydroxy group
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/12—Preparations containing hair conditioners

Definitions

• the present invention relates to a method for conditioning the hair. Specifically, acylated derivatives of triethanolamine are provided that give improved hair conditioning compositions, particularly for clear, or translucent liquid compositions.
• Scalp hair becomes soiled due to its contact with the surrounding environment and from sebum secreted from the hair follicles.
• the build-up of sebum and environmental soiling can cause the hair to have a dirty or greasy feel, and an unattractive appearance.
• shampooing the hair removes excess sebum and other environmental soiling.
• the shampooing process has disadvantages in that the hair is left in a wet, tangled and generally unmanageable state.
• Shampooing can also result in the hair becoming dry and frizzy, and a loss of lustre, due to removal of natural oils or other hair moisturizing materials.
• the hair can also suffer from a loss of "softness" perceived by the user upon drying.
• the hair can also suffer from increased levels of static upon drying after shampooing. This can interfere with combing and can result in fly-away hair.
• conditioners which provide increased hair volume at the same time as providing conditioning/detangling benefits.
• each R in a compound is a ⁇ -C ) • preferably with onlv minimal, or no. C 0 _] (), hydrocarbjl group, preferably hav ing an Iodine Value (hereinafter also referred to as IV) of from about 70 to about 140 based upon the IV of the equivalent acid, n is a number from 1 to three on the weight average in anv mixture of compounds.
• each Ri in a compound is a C ] _"$ alkyl or h droxy alkyl group, the total of n and the number of R ' groups that are hy droxyethy l groups equaling 3.
• n-m equaling 4.
• X is a hair conditioner compatible anion. preferably methyl sulfate.
• the cis: trans isomer ratio of the fatty acid (of the ( ' 18: 1 component) is at least about 1 :1. preferably about 2:1. more preferably 3:1, and even more preferably about 4:1. or higher.
• the compound, or mixtures of compounds have (a) either a Hunter "I " transmission of at least about 85. typically from about 85 to about 95. preferably from about 90 to about 95. more preferably above about 95. if possible; (b) only very low. e.g., non-detectable levels, at the conditions of use. of odorous compounds selected from the group consisting of: isopropyl acetate; 2.2'-ethylidenebis(oxy)bispropane; 1.3.5- trioxane: and/or short chain fatty acid (4-12. especially 6-10. carbon atoms) esters, especially methyl esters: or (c) preferably, both.
• odorous compounds selected from the group consisting of: isopropyl acetate; 2.2'-ethylidenebis(oxy)bispropane; 1.3.5- trioxane: and/or short chain fatty acid (4-12. especially 6-10. carbon atoms) esters, especially methyl esters: or (c) preferably, both
• the level of conditioning agent containing polyunsaturated alkylene groups is preferably at least about 3% by weight of the total conditioning agent present and preferably the conditioning agent comprises a mixture of monoester and diester.
• the method of the present invention provides excellent in-use wet feel, excellent clean feel during rinsing and post-rinsing, good dry clean feel and excellent detangling, in addition to minimizing volume loss versus methods using conventional conditioning compositions.
• concentrations and ratios herein are by weight of composition, unless otherwise specified.
• Surfactant chain lengths are also on a weight average chain length basis, unless otherwise specified.
• the method of the present invention comprises applying to the hair an effective amount of a conditioner composition wherein the conditioner composition comprises a mono-ol or diol solvent having a ClogP of from about 0.15 to about 0.64 and a quaternary ammonium cationic conditioning agent.
• the conditioner composition comprises a mono-ol or diol solvent having a ClogP of from about 0.15 to about 0.64 and a quaternary ammonium cationic conditioning agent.
• the conditioning compositions of the present invention also comprise a principal solvent system in addition to water. This is particularly important for formulating liquid, clear hair conditioning compositions.
• the principal solvent preferably comprises less than about 40%, preferably from about 5% to about 35%, more preferably from about 5% to about 20%, and even more preferably from about 5% to about 15%, by weight of the composition.
• the principal solvent is selected to minimize solvent odor impact in the composition and to provide a low viscosity to the final composition.
• isopropyl alcohol is not very effective and has a strong odor.
• n-Propyl alcohol is more effective, but also has a distinct odor.
• butyl alcohols also have odors but can be used for effective clarity/stability, especially when used as part of a principal solvent system to minimize their odor.
• the alcohols are also selected for optimum low temperature stability, that is they are able to form compositions that are liquid with acceptable low viscosities and translucent, preferably clear, down to about 40°F (about 4.4°C) and are able to recover after storage down to about 20°F (about 6.7°C).
• Suitable solvents for use herein can be selected based upon their octanol/water partition coefficient (P).
• Octanol/water partition coefficient of a principal solvent is the ratio between its equilibrium concentration in octanol and in water.
• the partition coefficients of the principal solvent ingredients of this invention are conveniently given in the form of their logarithm to the base 10, logP.
• the logP of many ingredients has been reported; for example, the Pomona92 database, available from Daylight Chemical Information Systems, Inc. (Daylight CIS), Irvine, California, contains many, along with citations to the original literature. However, the logP values are most conveniently calculated by the "CLOGP” program, also available from Daylight CIS. This program also lists experimental logP values when they are available in the Pomona92 database.
• the "calculated logP” (ClogP) is determined by the fragment approach of Hansch and Leo (cfi, A. Leo, in Comprehensive Medicinal Chemistry, Vol. 4, C. Hansch, P. G. Sammens, J. B. Taylor and C. A. Ramsden, Eds., p.
• ClogP values which are the most reliable and widely used estimates for this physicochemical property, are preferably used instead of the experimental logP values in the selection of the principal solvent ingredients which are useful in the present invention.
• Other methods that can be used to compute ClogP include, e.g., Crippen's fragmentation method as disclosed in J. Chem. Inf. Comput. Sci.. 27, 21 (1987);
• the principal solvents herein are selected from those having a ClogP of from about 0.15 to about 0.64, preferably from about 0.25 to about 0.62, and more preferably from about 0.40 to about 0.60, said principal solvent preferably being at least somewhat asymmetric, and preferably having a melting, or solidification, point that allows it to be liquid at, or near room temperature. Solvents that have a low molecular weight and are biodegradable are also desirable for some purposes.
• Operable principal solvents are disclosed and listed below which have ClogP values which fall within the requisite range. These include mono-ols, C6 diols, C7 diols, octanediol isomers, butanediol derivatives, trimethylpentanediol isomers, ethylmethylpentanediol isomers, propyl pentanediol isomers, dimethylhexanediol isomers, ethylhexanediol isomers, methylheptanediol isomers, octanediol isomers, nonanediol isomers, alkyl glyceryl ethers, di(hydroxy alkyl) ethers, and aryl glyceryl ethers, aromatic glyceryl ethers, alicyclic diols and derivatives, C3C7 diol alk
• Particularly preferred principal solvents include hexanediols such as 1 ,2-Hexanediol and 2-Ethyl-1.3-hexanediol and pentanediols such as 2,2,4-Trimethyl-l,3-pentanediol. These principal solvents are all disclosed in copending U.S.
• Especially preferred for use in the hair conditioning compositions herein is 1,2- hexanediol.
• the clear compositions can optionally, but preferably, contain an effective amount, sufficient to improve clarity, of low molecular weight water soluble solvents like ethanol. isopropanol. propylene glycol. 1.3-propanediol. propylene carbonate. butanol etc.. said water soluble solvents being at a level that will not form clear compositions by themselves.
• a second essential ingredient of the compositions herein is a quaternary ammonium conditioning agent, preferably present at a level of from about 1% to about 25%, preferably from about 5% to about 20%, more preferably from about 5% to about 15%, by weight of the conditioning composition.
• An essential substituted quaternary ammonium compound for use herein may be defined a Diester Quaternary Ammonium active (DEQA) selected from compounds having the formula:
• each R in a compound is a C ' 6- ⁇ 22 hydrocarbyi group, preferably ha ing an IV from about 70 to about 140 based upon the IV of the equivalent fatly acid with the cis/trans ratio preferably being as described hereinafter, n is a number from 1 to three on the weight average in any mixture of compounds, each R ⁇ in a compound is a C j _3 alky l or hydroxy alkyl group, the total of n and the number of R ⁇ groups that arc hydro xyethyl groups equaling 3. n ⁇ m equaling 4. and X is a hair conditioner compatible anion.
• the cis:trans isomer ratio of the fatty acid (of the C 18 : 1 component) is at least about 1.1. preferably about 2: 1. more preferably 3: 1. and even more preferably about 4:1. or higher.
• I he compound, or mixtures of compounds have (a) either a Hunter "I " transmission of at least about 85. typically from about 85 to about 95. preferably from about 90 to about 95. more preferably above about 95. if possible, (b) only low. relatively non-dectectable levels, at the conditions of use, of odorous compounds selected irom the group consisting of: isopropyl acetate: 2.2'-ethylidcnebis(oxy)bispropanc: 1.3.5- trioxane; and or short chain fatty acid (4-12. especially 6-10. carbon atoms) esters, especially methyl esters; or (c) preferably , both.
• the Hunter I, transmission is measured by (] ) mixing the conditioning active with solvent at a level of about 10% of active, to assure clarity, the preferred solvent being ethoxylated (one mole IT ) ) 2.2,4-trimeth l-1.3-pcntanediol and (2) measuring the L color value against distilled water with a Hunter ColorQUhSl ® colorimeter made by Hunter Associates Laboratory . Reston. Virginia.
• I he level of odorant is defined by measuring the level of odorant in a headspacc ov er a sample of the conditioning active (about 92% active). Chromatograms are generated using 200 mL of head space sample over about 2 grams of sample. ' I he head space sample is trapped on to a solid absorbent and thermally desorbed onto a column directly via cryofocussing at about -100°C. I he identifications of materials is based on the peaks in the chromatograms. Some impurities identified are related to the solvent used in the quaternization process, (e.g.. ethanol and isopropanol). The ethoxy and methoxy ethers are typically sweet in odor. There are , -C g methy l esters found in the current commercial samples, but not in the typical conditioner acti es of this invention.
• esters contribute to the perceived poorer odor of the current commercial samples.
• I he acceptable level of each odorant is as follows: isopropyl acetate should be less than about 5. preferably less than about 3. and more preferably less than about 2.
• nanograms per liter ( ⁇ g/ ): 2.2'-cthylidenebis(oxy )bispropane should be less than about 200. preferably less than about 100, more preferably less than about 10. and even more preferably less than about 5.
• nanograms per liter ( ⁇ g L.): 1.3.5-trioxane should be less than about 50, preferably less than about 20. more preferably less than about 10. and even more preferably less than about 7.
• nanograms per liter ( ⁇ g I .) and/or each short chain fatty acid (4-12. especially 6-10. carbon atoms) ester, especially methyl esters should be less than about 4. preferably less than about 3. and more preferably less than about 2. nanograms per liter ( ⁇ g L ).
• the reaetants are selected to have good odor and color.
• the reaetants can be cleaned up prior to use.
• the fatly acid reactant can be double or triple distilled to remove color and odor causing bodies and remove short chain fatty acids.
• the color of the triethanolamine reactant needs to be controlled to a low color level (e.g. a color reading of about 20 or less on the API IA scale).
• the degree of clean up required is dependent on the level of use and the presence of other ingredients. For example, adding a dye can cover up some colors. However, for clear and/or light colored products, the color must be almost non-detectable. This is especially true for higher levels of active, e.g., from about 8% to about 75%, preferably from about 13% to about 60%. more preferably from about 18% to about 40%. of the conditioner active by weight of the composition.
• the odor can be covered up by higher levels of perfume, but at the higher levels of conditioner active there is a relatively high cost associated with such an approach, especially in terms of having to compromise the odor quality. Odor quality can be further impro ed by use of ethanol as the quaternizalion reaction solv ent.
• Preferred biodegradable hair conditioning compounds comprise quaternary ammonium salt, the quatemized ammonium salt being a quaternized product of condensation between: a)-a fraction of saturated or unsaturated, linear or branched fatly acids, or of derivativ es of said acids, said fatty acids or derivatives each possessing a hydrocarbon chain in which the number of atoms is between 5 and 21 , and b)-triethanolamine. characterized in that said condensation product has an acid value, measured by titration of the condensation product with a standard K.OH solution against a phcnolphthalein indicator, of less than about 6.5.
• I he acid value is preferably less than or equal to about 5. more preferably less than about 3. Indeed, the lo er the AV, the belter softness performance is obtained.
• the acid value is determined by titration of the condensation product with a standard KOH solution against a phenolphthalein indicator according to 1SO#53402.
• the AV is expressed as mg KX)1 1/g of the condensation product.
• the reaetants are present in a molar ratio of fatty acid fraction to triethanolamine of from about 1 :1 to about 2.5: 1.
• Preferred cationic. preferably biodegradable quaternary , ammonium hair conditioning compounds can contain the group -(O)CR which is deriv ed from animal fats, unsaturated. and polyunsaturated, fatty acids, e.g., oleic acid, and/or partially hydrogenated fatty acids, derived from vegetable oils and/or partially hydrogenated vegetable oils, such as. canola oil. safflowcr oil, peanut oil. sunilower oil. corn oil. soybean oil. tall oil. rice bran oil, etc.
• Non-limiting examples of fatty acids (FA) have the following approximate distributions:
• TPU is the percentage of polyunsalurates present.
• FA's of this invention aie as follows:
• I A D is prepared from a soy bean fatty acid
• I A ' is prepared from a slightly hydrogenated tallow fatty acid.
• I he more preferred essential hair conditioning actives containing an effective amount of molecules containing two ester linked hydrophobic groups [RC(CO)O-], said actives being referred to hereinafter as "DhQA's”, are those that are prepared as a single DEQA irom blends of all the different fatty acids that are represented (total fatty acid blend), rather than from blends of mixtures of separate finished DFQA's that are prepared from different portions of the total fatty acid blend.
• the fatty acyl groups are unsaturated. e.g.. from about 50% to 100%). preferably from about 55% to about 95%. more preferably from about 60% to about 90%. and that the total level of active containing polyunsaturated fatty acy l groups (TPU) be preferably from about 3%) to about 30%.
• the cis/trans ratio for the unsaturated fatty acy 1 groups is usually important, ith the cis trans ratio being from about 1 : 1 to about 50: 1. the minimum being about 1 : 1. preferably at least 3: 1. and more preferably from about 4: 1 to about 20: 1. (As used herein, the "percent ol conditioner activ e" containing a given R group is the same as the percentage of that same R group is to the total R groups used to form all of the conditioner actives.)
• the highly unsaturated materials are also easier to formulate into concentrated premixes that maintain their low viscosity and are therefore easier to process, e.g.. pump, mixing, etc.
• These highly unsaturated materials ( total lev el of active containing polyunsaturated fatty acy l groups ( " I PL " ) being t pically from about 3% to about 30%. with only the low amount of solvent that normally is associated with such materials, i.e.. from about 5% to about 20%. preferably from about 8% to about 25%. more preferably from about 10% lo about 20%>. weight of the total conditioner, solvent mixture, are also easier to formulate into concentrated, stable compositions of the present invention, even at ambient temperatures.
• a preferred long chain DFQA is the DFQA prepared from sources containing high levels of poly unsaturation. i.e.. melhylhydroxyethy lammonium methyl sulfate. where the acy l is derived from fatty acids containing sufficient polyunsaluration. e.g.. mixtures of tallow fatty acids and soybean fatty acids.
• Another preferred long chain DKQA is the diole l (nominally) DKQA, i.e.. DCQ ⁇ in which N.N-di(oleoy l-oxyelhyl)-N. -melhylhydroxyethy lammonium methyl sulfate is the major ingredient.
• Preferred sources of fatty acids for such DFQAs aie vegetable oils, and/or partially hydrogenated v egetable oils, with high contents ol unsaturated. e.g.. oleoyl groups.
• the DEQA diester when specified, it can include the monoester (n I ) and or tricster (n 3) that are present.
• the DEQA can include the monoester (n I ) and or tricster (n 3) that are present.
• at least about 30% of the DEQA is in the diester form, and Irom 0% to about 30% can be DEQA monoester.
• ' I he overall ratios of diester quat to monoester quat are from about 2.5: 1 to about 1.1. preferably from about 2.3:1 to about 1.3:1.
• the level of monoester present can be controlled in manufacturing the DFQA by vary ing the ratio of fatly acid, or fatty acyl source, to triethanolamine.
• the overall ratios of diester qual to tricster quat are from about 10: 1 to about 1.5T. preferably from about 5: 1 to about 2.8: 1.
• each R is a hydrocarby . or substituted hydrocarby l. group, preferably, alky , monounsaturatcd alkenyl. and polyunsaturated alkenyl groups, with the conditioner active containing polyunsaturated alkeny l groups being preferably at least about 3%, more preferably at least about 5%. more preferably at least about 10%. and even more preferably at least about 15%. by weight of the total conditoncr active present; the actives preferably containing mixtures of R groups, especially within the individual molecules.
• RC(())() is derived from unsaturated fatty acid. e.g..
• oleic acid and or fatty acids and'oi partially hydrogenated fatty acids, deriv ed from animal la .
• vegetable oils and or partially hydrogenated vegetable oils such as: canola oil: safflowcr oil; peanut oil; sunflower oil: soybean oil: corn oil: tall oil: rice bran oil: etc.]
• DEQA biodegradable actives containing ester linkages arc referred to as "DEQA”. which includes both diester, triester. and monoester compounds containing from one to three, preferably two. long chain hydrophobic groups.
• These actives have the characteristic that they can be processed by conventional mixing means al ambient temperature, at least in the presence of about 15% of solvent C. as disclosed hereinbefore.
• I he DFQAs herein can also contain a low level of fatty acid, which can be from unreacted starting material used to lor the DEQA and/or as a by-product of any partial degradation (hydrolysis) of the conditioner active in the finished composition. It is preferred that the level of free atty acid be low . preferably below about 15%. more preferably below about 10%. and even more preferably below about 5%. by weight of the conditioner active.
• the actives of the present inv ention are preferably prepared by a process wherein a chelant, preferably a diethylenetriammepentaacetate (DTP ⁇ ) and or an ethylene diamine- -disuccinate (LDDS) is added to the process. Also, preferably, antioxidants are added to the fatty acid immediately after distillation and or fractionation and'or during the esterification reactions and'or prior to. or during, the quatcrnization reaction, and or post-added lo the finished conditioner activ e, f he resulting conditioner active has reduced discoloration and malodor associated therewith.
• a chelant preferably a diethylenetriammepentaacetate (DTP ⁇ ) and or an ethylene diamine- -disuccinate (LDDS) is added to the process.
• antioxidants are added to the fatty acid immediately after distillation and or fractionation and'or during the esterification reactions and'or prior to. or during, the quatcrnization reaction, and or post-a
• he typical process comprises the steps of: a) prov iding a source of triglyccride and reacting the source of triglyceride to form a mixture of fatty acids and or fatty acid esters: b) using the mixture formed from step (a) lo react under esterii ⁇ eation conditions with triethanolamine; c) quaternizing. if desired, the mixture of fatly acid esters formed from step (b) by reacting the mixture under quaternizing conditions ith a quaternizing agent of the formula RAx wherein ⁇ is defined as in step (b) and X is a conditioner compatible anion. preferably selected from the group consisting of chloride, bromide, meth l sulfate.
• step (c) is carried out in the presence of a chelating agent selected from the group consisting ol diethylenetriamincpentaacetic acid. ethylenediamine- .Y-disuceinnic acid and mixtures thereof.
• a chelating agent selected from the group consisting ol diethylenetriamincpentaacetic acid. ethylenediamine- .Y-disuceinnic acid and mixtures thereof.
• I he step of reacting the source of triglyceride can further include reacting in the presence ol the chelating agent step (b) can further include the presence of the chelating agent.
• the total amount of added chelating agent is preferably within the range of from about 10 ppm to about 5,000 ppm, more preferably within the range of from about 100 pptn to about 2500 ppm by weight of the formed activ e.
• the source of triglyceride is preferably selected from the group consisting of animal fats, vegetable oils, partially hydrogenated vegetable oils, and mixtures thereof. More preferably, the vegetable oil or partially hy drogenated vegetable oil is selected from the group consisting of canola oil. partially hydrogenated canola oil, safflower oil. partially hydrogenated safflo er oil. peanut oil. partially hydrogenated peanut oil. sunflower oil. partially hydrogenated sunflower oil. corn oil. partially hydrogenated corn oil. soybean oil.
• the source of triglyceride is canola oil. partially hydrogenated canola oil, and mixtures thereof.
• ' I he process can also include the step of adding from about 0.01% to about 2% by weight of the composition of an antioxidant compound to any or all of steps (a), (b) or (c).
• the abov e processes produce a hair conditioner activ e with reduced coloration and malodor.
• the DEQA actives described hereinabove can contain a low level of the fatty acids which can be unreacted starting material and/or by-product of any partial degradation, e.g., hydrolysis, of the actives in the finished compositions. It is preferred that the level of free fatty acid be low, preferably below about 10%>, more preferably below about 5%, by weight of the active.
• conditioning actives and their methods of preparation are disclosed in US Application No. 60/044719.
• a commercially available diester quaternary ammonium compound for use herein has the tradename Tetranyl Co-40 and is supplied by Kao.
• the INCI name for this material is Dioleylethyl Hydroxyethylmonium methosulfate.
• a particularly preferred conditioning active for use herein is SC3 which is manufactured according to the synthesis example below.
• the quaternary ammonium conditioning agent is preferably present at a level of from about 1% to about 25%, preferably from about 5%> to about 20%>, more preferably from about 5% to about 15%>, by weight of the conditioning composition.
• Step 1 fatty alcohol compound synthesis: A mixture of about 1.200 grams of the hydrogenated oil from Synthesis Fxample I- (see below )and about 200 grams of the hydrogenated oil from Synthesis Example A (see below) is h drolyzed three times with about 250°C steam at about 600 psig for about 2.5 hours at a ratio of steam :oil of about
• the resulting mixture of fatty acids is vacuum distilled for a total of about 150 minutes, in which the pot temperature rose gradually from about 200 C C to about 238"C and the head temperature rose gradually from about 175°C to about 197 C C. Vacuum of about 0.3-0.6 mm is maintained.
• the fatty acids product of the vacuum distillation has an Iodine Value of about 99.1. an amine value (AV) of about 1 7.6 and a saponification value (SAP) of about 198.6.
• 1 he quaterni/ed material is optionally diluted with e.g. about 15% of an approximately 50:50 ethanol/ hexyleneglycol, preferably more hexylene glycol than ethanol. mixture which lowers the melting point of the material thereby prov iding a belter ease in the handling of the material.
• the hydrogen pressure is about 10 psig.
• a sample of the reaction mass is drawn and found to hav e an Iodine Value of about 78 and a cis:trans ratio of about 1.098.
• the hydrogen pressure is about 9.8 psig. fhe hydrogen feed is discontinued and the reactor contents cooled with stirring.
• the final reaction product has an Iodine Value of about 74.5 and a cis:trans ratio of about 1.35.
• the product that forms in the reactor is removed and filtered. It has a cloud point of about 22.2 C C 1 he chain length distributions of the acyl substituents on the sample taken at about 127 minutes, and of the final product, are determined to be as shown in 'I able 1 in which "sat " means saturated, and “mono” and “di” means monounsaturated and diunsaturated. respectively .
• Ealtv Acid Compound Synthesis Example B About 1.300 grams of food grade canola oil and about 5.2 grams of Engelhard "N-545"® nickel hydrogenation catalyst are placed in a hydrogenation reactor which is equipped w ith a stirrcr. 1 he reactor is scaled and evacuated, fhe contents arc heated to about 175°C and hydrogen is fed into the reactor. Stirring is maintained at about 450 rpm throughout the course of reaction. After about 5 minutes the temperature in the reactor is about 190X and the hydrogen pressure is about 7 psig. The temperature is held at about 190°C. After about 125 minutes from the start of the hydrogen feed, the hydrogen pressure is about 7 psig. A sample of the reaction mass is drawn and found to have an Iodine Value of about 85.4.
• N-545"® nickel hy drogenation catalyst arc placed in a hydrogenation reactor which is equipped with a stirrcr. T he reactor is sealed and evacuated. The contents are heated to about l SO ⁇ C and hv drogen is fed into the reactor. Stirring is maintained at about 450 rpm throughout the course of the reaction. After about 5 minutes the temperature in the reactor is about 1 2°C and the hydrogen pressure is about 10 psig. ' fhe temperature is held at about 190 ⁇ 3 C. After about 105 minutes from the start of the hydrogen feed, the hydrogen pressure is about 10 psig. A sample of the reaction mass is drawn and found to have an Iodine Value of about 85.5. After another about 20 minutes al about 190°C.
• the hydrogen pressure is about 10 psig.
• the hydrogen feed is discontinued and the reactor contents cooled with stirring.
• the final reaction product has an Iodine Value of about 82.4.
• ' fhe product that forms in the reactor is removed and filtered. It has a cloud point of about 17.2°C.
• Fattv Acid Compound Synthesis Example D About 1.300 grams of food grade canola oil and about 1 .4 grams of Engelhard "N-545"® nickel hydrogenation catalyst are placed in a hydrogenation reactor which is equipped with a stirrcr. ' fhe reactor is sealed and evacuated, ' fhe contents are heated to about 1 0°C and hydrogen is fed into the reactor. After about 5 minutes the temperature in the reactor is about 191 C and the hydrogen pressure is about 10 psig. The temperature is held at about 190 3 c C. After about 100 minutes from the start of the hydrogen feed, the hydrogen pressure is about 10 psig. A sample of the reaction mass is drawn and found to have an Iodine Value of about 95.4.
• the hydrogen pressure is about 10 psig.
• the hydrogen feed is discontinued and the reactor contents cooled with stirring.
• the final reaction product had an Iodine Value of about 2.3.
• the product that forms in the reactor is removed and filtered. It has a cloud point of about 34°C.
• Fattv Acid Compound S y nthesis Example E About 1.300 grams of food grade canola oil and about 1.3 grams of Engelhard "N-545"® nickel h drogenation catalyst are placed in a hydrogenation reactor which is equipped with a stirrcr. The reactor is sealed and evacuated. The contents are heated to about 190 ⁇ C and hydrogen is fed into the reactor to a hydrogen pressure of about 5 psig. After about 3 hours from the start of the hydrogen feed, a sample of the reaction mass is drawn and found to hav e an iodine value of about 98. The hydrogenation is interrupted, another about 0.7 grams of the same catalyst is added, and the reaction conditions arc reestablished at about 190°C for another about 1 hour.
• he quaternized material is optionally diluted with e.g. about 15% of ethanol which lowers the melting point of the material thereby prov iding a better handling of the material.
• the quaternized material is optionally diluted with e.g. about 8% of ethanol which lower the melting point of the material thereby providing a better case in the handling of the material.
• I he above synthesized compounds have a Hunter E transmission of about 90 and the following levels of odorants in ⁇ g L: Isopropyl acetate about 1. typically non- detcctablc: 1.3,5-trioxanc about 5.3: 2.2'-ethylidcnebis(oxy)-bispropane about 1. typically non-detectable; C6 methyl ester about 1. typically non-detectable: C8 Viethyl ester ⁇ " about 1. typically non-detectable; and CIO Viethyl ester * ' about I. typically non- detectable.
• sy nthesized conditioner compound arc also exemplified below in the non-limiting hair conditioning composition examples. Abbreviations used in the Examples
• the abbrev iated component identification have the following meanings:
• compositions herein can contain a wide variety of optional ingredients, non-limiting examples of which are described hereinbelow.
• the conditioning compositions herein can comprise an emollient selected from polyethylene glycol derivatives of triglyceride, polypropylene and polyethylene glycol ethers of glucose and polypropylene glycol ethers of fatty alcohol, and mixtures thereof, preferably a water-soluble emollient.
• the compositions preferably comprise from about 0.1% to about 10%, preferably 0.1%) to about 5%, by weight, of the emollient.
• Suitable polyethylene glycol derivatives of glycerides include any polyethylene glycol derivative of glycerides which are water-soluble and which are suitable for use in a hair conditioning composition.
• Suitable polyethylene glycol derivatives of glycerides for use herein include derivatives of mono-, di- and tri-glycerides and mixtures thereof.
• polyethylene glycol derivatives of glycerides suitable herein are polyethyleneglycol glyceryl fatty esters having the formula (1):
• n the degree of ethoxylation, is from about 4 to about 200, preferably from about 5 to about 100, more preferably from about 6 to about 80, and wherein R comprises an aliphatic radical having from about 5 to about 25 carbon atoms, preferably from about 7 to about 20 carbon atoms.
• Suitable polyethylene glycol derivatives of glycerides include PEG-20 almond glycerides, PEG-60 almond glycerides, PEG-11 avocado glycerides, PEG-6 capric/caprylic glycerides, PEG-8 capric/caprylic glycerides, PEG-20 corn glycerides, PEG-60 corn glycerides, PEG-60 evening primose glycerides, PEG-7 glyceryl cocoate, PEG-30 glyceryl cocoate, PEG-40 glyceryl cocoate, PEG-78 glyceryl cocoate, PEG-80 glyceryl cocoate, PEG- 12 glyceryl dioleate, PEG- 15 glyceryl isostearate, PEG-20 glyceryl isostearate, PEG-30 glyceryl isostearate, PEG-75 cocoa butter glycerides, PEG- 20 hydrogenated palm oil glycerides, PEG-70 mango g
• Preferred for use herein is a polyethylene glycol derivative of sunflower oil commerically available from Floratech under the tradename Florasun PEG- 10.
• Suitable polyalkylene glycol ethers of glucose for use herein include any water-soluble polyalkylene glycol ether of glucose suitable for use in a hair conditioning composition.
• Preferred herein are polyethylene glycol ether and polypropylene glycol ethers of glucose. Suitable examples include PPG- 10 methylglucose ether, PPG-20 ethyl glucose ether, Methyl Gluceth-20 and Methyl Gluceth-10. Mixtures of polyalkylene glycol ethers of glucose can also be used herein.
• Suitable polypropylene glycol ethers of fatty alcohol for use herein include any water- soluble polypropylene glycol ether of fatty alcohol suitable for use in a hair conditioning composition. Suitable examples include PPG-3 myristylether and PPG-2 myristyl ether propionate. Mixtures of polypropylene glycol ethers of fatty alcohols can also be used herein.
• compositions herein Most preferred for use in the compositions herein is a polypropylene glycol ether of a glyceride.
• the conditioning compositions of the present invention optionally comprise from about 0.1%) to about 10%o, preferably from about 1%> to about 5%, more preferably from about 2% to about 4%, by weight of the composition of water soluble organic solvent which does not have the appropriate ClogP value given above.
• Suitable such organic solvents for use herein are e.g., ethanol; isopropanol; 1 ,2-propanediol; 1,3-propanediol; propylene carbonate, butylene glycol, etc., preferably 1,3-butylene glycol.
• the hair conditioning compositions herein can also comprise a wide variety of additional ingredients which are known for use in conventional hair conditioning compositions, non-limiting examples of which are given below.
• the conditioning compositions herein may contain one or more monohydric fatty alcohols.
• Suitable fatty alcohols for use herein are fatty alcohols having a melting point of 30°C or lower being preferably selected from unsaturated straight chain fatty alcohols, saturated branched chain fatty alcohols, saturated C -Ci 2 straight chain alcohols, and mixtures thereof.
• the fatty alcohol is preferably used at a level of from about 0.1% to about 10%>, by weight, preferably from about 0.1 % to about 5%, more preferably from about 0.25% to about 1%>.
• the unsaturated straight chain fatty alcohols will typically have one degree of unsaturation.
• Di- and tri- unsaturated alkenyl chains may be present at low levels, preferably less than about 5%> by total weight of the unsaturated straight chain fatty alcohol, more preferably less than about 2%, most preferably less than about 1%.
• the unsaturated straight chain fatty alcohols will have an aliphatic chain size of from C12-C22 more preferably from Cj2-C ⁇ g, most preferably from Ci g-Ci g.
• Especially preferred alcohols of this type include oleyl alcohol and palmitoleic alcohol.
• the branched chain alcohols will typically have aliphatic chain sizes of from Cj2 _ C22' preferably C14-C20, more preferably Cig-Cjg.
• Exemplary branched chain alcohols for use herein include isostearyl alcohol, octyl dodecanol, and octyl decanol.
• saturated C -Cj2 straight chain alcohols include octyl alcohol, caprylic alcohol, decyl alcohol, and lauryl alcohol.
• compositions are preferably limited to levels of fatty alcohols, such as cetyl alcohol and stearyl alcohol, of no more than about 5%, preferably no more than about 1%), more preferably 0%, by weight of the composition.
• fatty alcohols such as cetyl alcohol and stearyl alcohol
• the conditioning compositions herein may also comprise from about 0.1% to about 10%), by weight, preferably from about 0.2%) to about 5%, more preferably from about 0.5% to about 3%, of a polymer of ethylene oxide, propylene oxide, and mixtures thereof, having the general formula:
• n has an average value of from about 2,000 to about 14,000, preferably from about 5,000 to about 9,000, more preferably from about 6,000 to about 8,000.
• these materials are polymers of ethylene oxide, which are also known as polyethylene oxides, polyoxyethylenes, and polyethylene glycols.
• R is methyl
• these materials are polymers of propylene oxide, which are also known as polypropylene oxides, polyoxypropylenes, and polypropylene glycols.
• R is methyl, it is also understood that various positional isomers of the resulting polymers can exist.
• n has an average value of from about 2,000 to about 14,000, preferably from about 5,000 to about 9,000, more preferably from about 6,000 to about 8,000.
• Polyethylene glycol polymers useful herein that are especially preferred are PEG-2M wherein R equals H and n has an average value of about 2,000 (PEG 2-M is also known as Polyox WSR® N-10 from Union Carbide and as PEG-2,000); PEG-5M wherein R equals H and n has an average value of about 5,000 (PEG 5-M is also known as Polyox WSR® N-35 and Polyox WSR® N-80, both from Union Carbide and as PEG-5,000 and Polyethylene Glycol 300,000); PEG-7M wherein R equals H and n has an average value of about 7,000 (PEG 7-M is also known as Polyox WSR® N-750 from Union Carbide); PEG-9M wherein R equals H and n has an average value of about 9,000 (PEG 9-M is also known as Polyox WSR® N-3333 from Union Carbide); and PEG- 14 M wherein R equals H and n has an average value of about 14,000 (PEG
• polymers include the polypropylene glycols and mixed polyethylene/polypropylene glycols.
• compositions herein can comprise conditioning agents in addition to the quaternary ammonium conditioning agents described hereinabove.
• Suitable conditioning agents include cationic surfactants, cationic polymers, nonvolatile silicones, nonvolatile hydrocarbons, saturated C14 to C22 straight chain fatty alcohols, nonvolatile hydrocarbon esters, and mixtures thereof.
• Suitable conditioning agents are disclosed in WO95/20939 which is incorporated herein by reference.
• additional ingredients can be formulated into the present conditioning compositions.
• these include hair-hold polymers, detersive surfactants such as anionic, nonionic, amphoteric, and zwitterionic surfactants, additional viscosity modifying agents and suspending agents such as xanthan gum, guar gum, hydroxypropyl guar, hydroxyethyl cellulose, methyl cellulose, hydroxyethylcellulose, starch and starch derivatives; viscosity modifiers such as methanolamides of long chain fatty acids such as cocomonoethanol amide; crystalline suspending agents; pearlescent aids such as ethylene glycol distearate; preservatives such as benzyl alcohol, methyl paraben, propyl paraben and imidazolidinyl urea; polyvinyl alcohol; ethyl alcohol; pH adjusting agents, such as citric acid, sodium citrate, succinic acid, phosphoric acid, sodium hydroxide, sodium carbonate; salts, inf
• the conditioning compositions herein can be formulated in a wide variety of product forms, including but not limited to creams, gels, aerosol and non-aerosol foams, mousses and sprays.
• Mousses, foams and sprays can be formulated with propellants such as propane, butane, pentane, dimethylether, hydroflurocarbon, CO2, N2O, or without propellants (using air as the propellant in a pump spray or pump foamer package).
• the conditioning composition herein may be used in a conventional manner for conditioning human hair.
• an effective amount of the conditioner composition typically from about 1 gram to about 50 grams, preferably from about 1 gram to about 25 grams, is then applied to the hair.
• Application of the conditioner typically includes working the composition through the hair, generally with the hands and fingers, or with a suitable implement such as a comb or brush.
• the conditioner composition is preferably then rinsed from the hair with water, but can also be left on the hair..
• the preferred method for conditioning the hair therefore comprises the steps of: (a) applying an effective amount of the conditioning composition to hair which has been shampooed, (b) working the conditioning composition into the hair with hands and fingers or with a suitable implement, (g) rinsing the conditioning composition from the hair using water.
• the conditioner herein can be left on the hair instead of being rinsed out.
• conditioning compositions of the present invention can be prepared by using conventional mixing and formulating techniques.
• Tetranyl Co-40 and hexanediol are added to the mixing vessel. Agitation is begun slowly. The butylene glycol is added and heated to 40°C. Agitation is continued and the methyl and propyl paraben is added at 40°C and allowed to dissolve. The composition is then cooled. With agitation the remaining ingredients are added while cooling. The perfume is added at about 25°C. The water is added and mixed until homogeneous. The pH is adjusted to 3.5 with sodium hydroxide.
• the resulting liquid concentrate is put into a suitable spray gel can.
• Example IX-X The pH target for the compositions of Example IX-X is pH 3-4 which is adjusted using sodium hydroxide (32%>/l .ON).
• the Examples IX-X can be prepared and packaged using conventional techniques such as those used hereinabove in the pump foamer examples.
• the conditioning compositions of the examples provide excellent hair detangling and wet clean feel on rinsing and post rinsing with the additional benefits of minimizing volume loss.

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• 1998
  • 1998-06-29 WO PCT/US1998/013923 patent/WO2000000169A1/en active Application Filing
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• 1999
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