WO2000000174A1 - Composition pour le traitement des cheveux par conditionneur - Google Patents

Composition pour le traitement des cheveux par conditionneur Download PDF

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Publication number
WO2000000174A1
WO2000000174A1 PCT/US1999/014716 US9914716W WO0000174A1 WO 2000000174 A1 WO2000000174 A1 WO 2000000174A1 US 9914716 W US9914716 W US 9914716W WO 0000174 A1 WO0000174 A1 WO 0000174A1
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Prior art keywords
hair
conditioning
composition according
conditioning composition
conditioning agent
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PCT/US1999/014716
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English (en)
Inventor
Michael Joseph Giret
Linda Helen Jacobs
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The Procter & Gamble Company
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Priority to AU49630/99A priority Critical patent/AU4963099A/en
Publication of WO2000000174A1 publication Critical patent/WO2000000174A1/fr

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    • 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
    • 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
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/608—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers

Definitions

  • the present invention relates to a hair conditioning composition.
  • 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 good hair volume at the same time as providing conditioning/detangling benefits.
  • a conditioning composition comprising a particular cationic conditioning agent, and a polyethylene glycol derivative of a glyceride provides a good in-use hair feel and conditioning, good clean feel on rinsing and post rinsing, good dry clean feel, together with excellent wet detangling and minimized dry hair volume loss typically experienced with conventional conditioning compositions.
  • the polyethylene glycol derivative of a glyceride is water soluble and therefore is rinsed out of the hair easily during rinsing, hence giving good in- use hair feel and conditioning and good wet clean feel on rinsing and post rinsing.
  • a hair conditioning composition comprising:
  • each R in a compound is a -C22 • preferably with onh minimal, or no. C 6-] ⁇ . hydrocarbyl group, preferably having an Iodine Value (hereinafter also referred to as IV) of from about 70 to about 140 based upon the IV of the equivalent fatty acid, n is a number from 1 to three on the w eight average in any mixture of compounds, each R* in a compound is a C 1.3 alkyl or hj droxy alkyl group, the total of n and the number of R! groups that are hydroxyethyl groups equaling 3. n-m equaling 4. and X ii a hair conditioner compatible anion. preferably methy l sulfate.
  • the conditioning agent preferably having (a) a Hunter L transmission of at least about 85. (b) non-detectable levels at the conditions of use of odorous compounds selected from isopropyl acetate. 2.2'-ethylidenebis(oxy)bispropane. and/or short laity acid esters or (c) preferably both. wherein preferably the level of conditioning agent containing polyunsaturated alkylene groups being at least about 3% by weight of the total conditioning agent present and preferably wherein the conditioning agent comprises a mixture of monoester and diester.
  • an emollient selected from polyethylene glycol derivative of a glyceride, a polypropylene glycol ether of a glucose and a polypropylene glycol ether of fatty alcohol.
  • the conditioning composition 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 conventional conditioning compositions.
  • composition levels, 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 conditioning composition of the present invention comprises a quaternary ammonium conditioning agent and an emollient.
  • 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 - 22 hydrocarby l group, preferably having an IV from about 70 to about 140 based upon the IV of the equivalent fatty acid with the cis/trans ratio preferably being as described hereinafter, n is a number from 1 to three on the weight av erage in any mixture of compounds, each IV in a compound is a C 1.3 alky l or hydroxy alkyl group, the total of n and the number of R ⁇ groups that are hydroxyethyl groups equaling 3. ⁇ -m equaling 4. and X is a hair conditioner compatible anion. preferably methyl sulfate.
  • the cis:trans isomer ratio of the fatty acid (of the C18: l component) is at least about 1 : 1. preierably 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) cither a Hunter "L" 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-decteclable levels, al the conditions of use. of odorous compounds selected from the group consisting of: isopropyl acetate; 2,2'-ethylidcncbis(oxy)bispropane: 1.3.5- trioxane: and'Or short chain fatty acid (4-12. especially 6-10. carbon atoms) esters, especially methy 1 esters: or (c) preferabl . both.
  • I he lluntct I transmission is measured by (1) mixing the conditioning active with sohent at a le ⁇ el of about 10% of active, to assure clarity, the preferred solvent being ethoxy lated (one mole LU) 2,2.4-trimethyl-1.3-pentanediol and (2) measuring the L color ⁇ alue against distilled water with a Hunter ColorQUEST® colorimeter made by Hunter Associates Laboratory. Rcston. Virginia.
  • ' 1 he level of odorant is defined by measuring the level of odorant in a headspace a sample of the conditioning active (about 92% active). Chromalogra s 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. The identifications of materials is based on the peaks in the chromatograms. Some impurities identified are related to the sohent used in the quaterni/ation process, (e.g.. ethanol and isopropanol). T he ethoxy and meihoxy ethers are typically sweet in odor. There are C 0 -Cp, methyl esters found in the current commercial samples, but not in the typical conditioner actives of this invention.
  • esters contribute to the perceived poorer odor of the current commercial samples.
  • the 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 L.); 2.2'-ethylidenebis(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-lrioxane 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/L.): 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 reactanls are selected to hav e good odor and color, for example, it is possible to obtain fatty acids, or their esters, for sources of the long fatty acyl group, that have good color and odor and which have extremely low levels of short chain ( 4_i2- especially C ⁇ .j Q fatty acyl groups.
  • the rcactants can be cleaned up prior to use.
  • the latty 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 lo a low color level (e.g. a color reading of about 20 or less on the API I A scale). 1 he degree of clean up required is dependent on the lev el of use and the presence of other ingredients. For example, adding a dy e 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 lev els 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 acti e 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 improved by use of ethanol as the quaterni/ation reaction solvent.
  • Preferred biodegradable hair conditioning compounds comprise quaternary ammonium salt, the quaternized ammonium salt being a quaternized product of condensation between: a)-a fraction of saturated or unsaturated. linear or branched laity acids, or of derivatives 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)-tricthanolamine. characterized in that said condensation product has an acid value, measured by litration of the condensation product with a standard KOH solution against a phenolphthalein indicator, of less than about 6.5.
  • he acid value is preferably less than or equal to about 5. more preferably less than about 3. Indeed, the lower the ⁇ V. the better softness performance is obtained.
  • he acid value is determined by titration of the condensation product with a standard KOFI solution against a phenolphthalein indicator according to ISO#53402. The AV is expressed as mg KOH g of the condensation product.
  • the reactants 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 derived 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. safflovver oil. peanut oil. sunflower oil, corn oil. soybean oil. tall oil. rice bran oil. etc.
  • Non-limiting examples of fatty acids (FA) have the follo ing approximate distributions:
  • TPU is the percentage of polyunsalurates present.
  • FA's of this invention are as follows:
  • a > is prepared from a soy bean fatty acid
  • FA? is prepared from a slightly hydrogenated tallow fatty acid.
  • Fhe more preferred essential hair conditioning actives containing an effective amount of molecules containing two ester linked hydrophobic groups (RC(CO)O-J, said acti es being referred to hereinafter as "DLOA's”, arc those that are prepared as a single DEQ ⁇ from blends of all the different fatty acids that are represented (total fatty acid blend), rather than from blends of mixtures of separate finished DHQA's that are prepared from different portions o ⁇ 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 acyl groups (TPU " ) be preferably from about 3% to about 30%.
  • the cis'trans ratio for the unsaturated fatty ac l groups is usually important, w 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 .
  • the "percent oi 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.
  • Fhe 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 level of active containing polyunsaturated fatty acy l groups ( ' I PL) being typically 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% to 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.
  • substituents R and IV can optionally be substituted with various groups such as alkoxyl or hydroxyl groups, and can be straight, or branched so long as the R groups maintain their basically hydrophobic character.
  • a preferred long chain DEQA is the DEQ ⁇ prepared from sources containing high levels of poly unsaturation. i.e., .N-di(ac melhylhydroxyelhylammoniimi meth l sulfate. where the acyl is deriv ed from fatty acids containing sufficient polyunsaturation. e.g.. mixtures of tallow fatty acids and soybean fatly acids.
  • Another preferred long chain DEQ ⁇ is the dioley l (nominally ) DEQ ⁇ . i.e.. DLQA in which N,N-di(oleoyl-oxyeth l)-N.N-methy hydroxyethy [ammonium methyl sulfate is the major ingredient.
  • Preferred sources of fatty acids for such DEQ ⁇ s are vegetable oils, and or partially hydrogenated vegetable oils, with high contents of unsaturated. e.g., oleoyl groups.
  • at least about 30% of the DEQA is in the diester form, and from 0% to about 30% can be DEQA monoester, e.g.. there are three R ⁇ group.
  • the 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.
  • ' 1 hc level of monoester present can be controlled in manufacturing the DEQ ⁇ by v arying the ratio ol fatty acid, or fatty acy l source, to triethanolamine.
  • I he overall ratios of diester quat to triester quat are from about 10: 1 to about 1.5: 1. preferably from about 5: 1 to about 2.8: 1.
  • Hie above compounds used as the essential biodegradable quaternized estcr-amine conditioning material in the practice of this invention, can be prepared using standard reaction chemistry.
  • an amine of the formula K(CH2 l2 ⁇ H)3 is esterified. preferably at two hydroxyl groups, with an acid chloride of the formula RC( ⁇ )Cl. to form an amine which can be made cationic by acidification (one R is FI) to be one type of conditioner, or then quaternized with an alkyl halidc, R ! X, to yield the desired reaction product (wherein R and IV are as defined hereinbefore).
  • this reaction sequence allows a broad selection of agents to be prepared.
  • each R is a hydr ⁇ carby l. or substituted hydrocarby 1. group, preferably, alk l, monounsaturated alken l, and polyunsaturated alkenv l groups, with the conditioner active containing polyunsaturated alkenvl groups being preferably at least about 3%, more preferably at least about 5%. more preferably at least about 10%. and even more preierably at least about 15%. by weight of the total conditoncr activ e present: the actives preferably containing mixtures of R groups, especially within the individual molecules.
  • RC(O)C is deriv ed from unsaturated fatty acid. e.g.. oleic acid, and/or fatty acids and/or partially hydrogenated fatty acids, derived from animal fats, vegetable oils and'or partially hydrogenated vegetable oils, such as: canola oil: safflower oil: peanut oil: sunflower oil: soybean oil: corn oil; tall oil: rice bran oil: etc.]
  • canola oil safflower oil: peanut oil: sunflower oil: soybean oil: corn oil; tall oil: rice bran oil: etc.
  • DEQ ⁇ similar biodegradable actives containing ester linkages
  • DEQ ⁇ which includes both diester. triester. and monoester compounds containing from one to three, preferably two. long chain hydrophobic groups.
  • the DEQ ⁇ s herein can also contain a low lev el of fatty acid, which can be from unreacted starting material used to form the DF ⁇ QA 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 fatty acid be low. preferably below about 15%, more preferably below about 10%. and even more preferably below about 5%. by weight of the conditioner activ c
  • the above compounds, used as the quaternized ester-amine conditioning active in the practice of this invention can be prepared using standard reaction chemistry.
  • an amine of the formula RN(CH2CH2OH)2 is esterified at both hydroxyl groups with an acid chloride of the formula R* C(O)Cl, then quaternized with an alkyl halide, RX, to yield the desired reaction product (wherein R and R ⁇ are as defined hereinbefore).
  • R and R ⁇ are as defined hereinbefore.
  • the actives of the present invention are preferably prepared by a process wherein a chelant, preferably a diethylenetriaminepentaacetatc (DTP A) and'or an cthylene diamine-N.N ' -disuccinate (EDDS) 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 quaternization reaction, and/or post-added to the finished conditioner active. The resulting conditioner active has reduced discoloration and malodor associated therewith.
  • a chelant preferably a diethylenetriaminepentaacetatc (DTP A) and'or an cthylene diamine-N.N ' -disuccinate (EDDS) 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 quatern
  • the typical process comprises the steps of: a) providing a source of triglyceride 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) to react under esterification conditions with triethanolamine; c) quaternizing. if desired, the mixture of fatty acid esters formed from step (b) by reacting the mixture under quaternizing conditions with a quaternizing agent of the formula R ⁇ X wherein R ⁇ is defined as in step (b) and X is a conditioner compatible anion. preferably selected from the group consisting of chloride, bromide, methy l sulfate. ethylsulfate.
  • step (c) is carried out in the presence of a chelating agent selected from the group consisting of diethylenetriamincpentaacetic acid. ethylenediamine- .N'-disuccinnic acid and mixtures thereof.
  • a chelating agent selected from the group consisting of diethylenetriamincpentaacetic acid. ethylenediamine- .N'-disuccinnic acid and mixtures thereof.
  • 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 ppm to about 2500 ppm by weight of the formed active.
  • 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 ot partially hydrogenated vegetable oil is selected from the group consisting oi canola oil. partially hy drogenated canola oil, safflower oil. partially hydrogenated safflovver oil. peanut oil, partially hydrogenated peanut oil. sunflower oil, partially hydrogenated sunflower oil. corn oil. partially hydrogenated corn oil. soybean oil. partially hydrogenated soybean oil.
  • the source of triglyceride is canola oil. partially hydrogenated canola oil. and mixtures thereof.
  • the 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 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: ⁇ mixture of about 1,200 grams of the hydrogenated oil from Synthesis Example F (see below and about 200 grams of the hydrogenated oil from Synthesis Example A (see below) is hy drol ccl three times with about 250°C steam at about 600 psig for about 2.5 hours at a ratio of stearmoil of about
  • Fhe 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 to about 238°C and the head temperature rose gradually from about 175°C to about 197°C. Vacuum of about 0.3-0.6 mm is maintained.
  • l he fatty acids product of the vacuum distillation has an Iodine Value of about 99.1. an amine value ( ⁇ V) of about 197.6 and a saponification value (SAP) of about 198.6.
  • the quaternized 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 providing a better 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 have an Iodine Value of about 78 and a cis:trans ratio of about 1.098.
  • the h drogen pressure is about 9.8 psig.
  • the 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. 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 monoun saturated and di unsaturated. respectively.
  • the hydrogen pressure is about 6 psig.
  • the hydrogen feed is discontinued and the reactor contents cooled ith stirring.
  • Iodine Value of about 80.
  • the product that forms in the reactor is removed and filtered. It has a cloud point of about 18.6°C.
  • 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. T he 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 ⁇ cid 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 stirrer. ' I he reactor is sealed and evacuated. 1 hc 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 hy drogen pressure is about 10 psig. " Fhe temperature is held at aboul 190 ⁇ 3T . A ter 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 lo 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.
  • T he product that forms in the reactor is removed and filtered. It has a cloud point of about 34°C.
  • Fattv Acid Compound Synthesis Example E Aboul 1.300 grams of food grade canola oil and about 1.3 grams of Engelhard "N-545"® nickel hydrogenation catalyst are placed in a hydrogenation reactor which is equipped ith a stirrer. 1 he reactor is scaled and evacuated. The contents are heated to about 190T 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 aboul 98. The hydrogenation is interrupted, another about 0.7 grams of the same catalyst is added, and the reaction conditions are reestablished at about 190°C for another aboul 1 hour. The hydrogen feed is then discontinued and the reactor contents cooled with stirring. 1 he final reaction product had an Iodine Value of about 89.9. The product that forms in the reactor is removed and filtered. It has a cloud point of about 16°C.
  • the quaternized material is optionally diluted with e.g. about 15% of ethanol which lowers the melting point of the material thereby providing a better handling of the material.
  • the quaternized material is optionally diluted with e.g. aboul 8% of ethanol which lower the melting point of the material thereby providing a better ease in the handling of the material.
  • 1 he quaternized material is optionally diluted with e.g. about 8% of ethanol which lower the melting point of the material thereby providing a belter ease in the handling of the material.
  • 1 he above synthesized compounds have a Flunlcr L transmission of about 90 and the following levels of odorants in ⁇ g'E: Isopropyl acetate -' about 1. typically non- detectable: 1.3.5-trioxane about 5.3; 2,2'-ethylidenebis(oxy )-bispropane ⁇ about 1. typically non-detectable; C6 methy l ester about 1. typically non-detectable: C8 Methy l ester -- about 1 , typically non-detectable; and C 10 Meth l ester about 1. typically non- detectable.
  • T he above synthesized conditioner compound are also exemplified below in the non-limiting hair conditioning composition examples.
  • SC3 Flair Conditioner compound as made according to Synthesis Example of conditioner compound 3
  • SC4 Hair Conditioner compound as made according to Sy nthesis Example of conditioner compound 4
  • TMP ⁇ 2.2.4-trimelhyl-1.3-pentanediol
  • 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.
  • the conditioning compositions herein comprise an emollient selected from polyethylene glycol derivatives of glyceride, 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 poly ethylenegly col 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 methyl 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-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 polyethylene glycol derivative of a glyceride.
  • Optional Components are a polyethylene glycol derivative of a glyceride.
  • compositions herein can contain a wide variety of optional ingredients, non-limiting examples of which are described hereinbelow.
  • Suitable principal solvents for use herein in addition to water 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.
  • ClogP The "calculated logP” 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. 295, Pergamon Press, 1990, incorporated herein by reference).
  • the fragment approach is based on the chemical structure of each ingredient, and takes into account the numbers and types of atoms, the atom connectivity, and chemical bonding.
  • ClogP values which are the most reliable and widely used estimates for this physicochemical property, are preferably used instead of the experimental logP values in the selection of the principal solvent ingredients which are useful in the present invention.
  • Other methods that can be used to compute ClogP include, e.g., Crippen's fragmentation method as disclosed in J. Chem. Inf. Comput. Sci., 27, 21 (1987); Viswanadhan's fragmentation method as disclose in J. Chem. Inf. Comput. Sci., 29, 163 (1989); and Broto's method as disclosed in Eur. J. Med. Chem. - Chim. Theor., 19, 71 (1984).
  • the principal solvents herein are selected from those having a ClogP of from about 0.15 to about 0.64, preferably from about 0.25 to about 0.62, and more preferably from about 0.40 to about 0.60, said principal solvent preferably being at least somewhat asymmetric, and preferably having a melting, or solidification, point that allows it to be liquid at, or near room temperature. Solvents that have a low molecular weight and are biodegradable are also desirable for some purposes.
  • 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-l,3-hexanediol and pentanediols such as 2,2,4-Trimethyl-l,3-pentanediol. These principal solvents are all disclosed in copending U.S.
  • a preferred principal solvent for use herein is 1,2-hexanediol.
  • the dispersion compositions of the present invention optionally comprise from about 0.1%) to about 10%, preferably from about 1% to about 5%, more preferably from about 2% to about 4%, by weight of the composition of water soluble organic solvent which does not have the appropriate ClogP value given above.
  • Suitable such organic solvents for use herein are e.g., ethanol; isopropanol; 1,2-propanediol; 1,3-propanediol; propylene carbonate, butylene glycol, etc., preferably 1,3-butylene glycol.
  • conditioning compositions herein may include a wide variety of additional ingredients, non-limiting examples of which are given below. Additional Conditioning Actives
  • the conditioning compositions herein may comprise other hair conditioning actives in addition to the DEQA of formula (1) as described above.
  • conditioning agents for use herein include, but are not limited to, quaternary ammonium conditioning agents, such as ester substituted quaternary ammonium compounds, amide substituted quaternary ammonium compounds and alkyl substituted quaternary ammonium compounds such as those quaternary ammonium compounds disclosed in US-A-5,610,187 (Witco) incorporated herein by reference, mixed amide/ester substitituted quaternary ammonium compounds such as those disclosed in EP-A-682935 (Kao) incorporated herein by reference and protonated amines.
  • quaternary ammonium conditioning agents such as ester substituted quaternary ammonium compounds, amide substituted quaternary ammonium compounds and alkyl substituted quaternary ammonium compounds such as those quaternary ammonium compounds disclosed in US-A-5,610,187 (Witco) incorporated herein by reference, mixed amide/ester substitituted quaternary ammonium compounds
  • a second type of DEQA active has the general formula:
  • each R is a methyl or ethyl group and preferably each R 1 is in the range of C ⁇ 5 to C19.
  • the diester when specified, it can include the monoester that is present. The amount of monoester that can be present is the same as in DEQA (1).
  • DEQA of formula (2) is the "propyl" ester quaternary ammonium active having the formula l,2-di(acyloxy)-3- trimethylammoniopropane chloride, where the acyl is the same as that of DEQA ⁇ , and is denoted hereinafter as DEQA ⁇ .
  • 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 -Cj2 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 Ci2-C22 more preferably from C
  • Especially preferred alcohols of this type include oleyl alcohol and palmitoleic alcohol.
  • the branched chain alcohols will typically have aliphatic chain sizes of from Cyi-Cyi, preferably C14-C20 more preferably Ci g-Cjg.
  • Exemplary branched chain alcohols for use herein include isostearyl alcohol, octyl dodecanol, and octyl decanol.
  • saturated Cg-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.
  • 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 14
  • 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 C]4 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; insoluble and soluble silicones (eg.
  • viscosity modifiers such as methanolamides of long chain fatty acids such as cocomonoethanol amide; crystalline suspending agents; pearlescent aids such as ethylene glycol distearate; preservatives such as benzyl alcohol, methyl paraben, propyl paraben and imidazolidinyl urea; polyvinyl alcohol; ethyl alcohol; pH adjusting agents, such as citric acid, sodium citrate, succinic acid, phosphoric acid, sodium hydroxide, sodium carbonate; salts, in general, such as potassium acetate and sodium chloride; coloring agents, such as any of the FD&C or D&C dyes; hair oxidizing (bleaching) agents, such as hydrogen peroxide, perborate and persulfate salts; hair reducing agents, such as the thioglycolates; perfumes; sequestering agents, such as disodium ethylenediamine tetra-acetate; and polymer plastic
  • conditioning compositions herein can be formulated in a wide variety of product forms, including but not limited to creams, gels, foams, mousses and sprays.
  • Mousses, foams and sprays can be formulated with propellants such as propane, butane, pentane, dimethylether, hydrofiurocarbon, 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 or skin.
  • an effective amount of the conditioner composition typically from about 1 gram to about 50 grams, preferably from about 1 gram to about 20 grams, is then applied to the hair or skin.
  • 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 or skin with water, but can also be left on the hair..
  • the preferred method for conditioning the hair therefore comprises the steps of:
  • 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.
  • the Tetranyl Co-40 and hexanediol are added to the mixing vessel. Agitation is begun slowly. The butylene glycol is added and heated to 40°C. Agitation is continued and the methyl and propyl paraben is added at 40°C and allowed to dissolve. The composition is then cooled. With agitation the remaining ingredients are added while cooling. The perfume is added at about 25°C. The water is added and mixed until homogeneous. The pH is adjusted to 3.5 with sodium hydroxide. The resulting liquid is put into a pump foamer package such as AIRSPRAY supplied by Zuiderkade.
  • AIRSPRAY supplied by Zuiderkade.
  • the resulting liquid from the process for preparation of the mousse is put into a suitable spray gel can.
  • a premix of the Jaguar and the butylene glycol is made by mixing the two ingredients at room temperature.
  • the Tetranyl Co-40 is added to the mixing vessel and agitation is begun with heating to 40°C. Agitation is continued and the methyl and propyl paraben is added at 40°C and allowed to dissolve.
  • the composition is cooled. With agitation, the conditioning ingredients are added, eg. Florasun, Silicone, while cooling.
  • the prefume is added at approximately 25°C.
  • the Jaguar/Butylene glycol premix is added and mixed until homogeneous.
  • the TiO 2 and water is added and mixed until homogeneous.
  • the pH is adjusted to 3.5 with sodium hydroxide.
  • Example V-VI prepared according to Synthesis Example SC3 hereinabove.
  • the pH target for the compositions of Example V-VI is pH 3-4 which is adjusted using sodium hydroxide (32%/l .ON).
  • the Examples V-VI 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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Abstract

L'invention concerne une composition pour le traitement des cheveux par conditionneur, qui renferme (a) un agent conditionneur cationique à ammonium quaternaire représenté par la formule (I) : [RC(O)OC2H4]nN+(R1)mX- Dans ladite formule, chaque R présent dans un composé est un groupe hydrocarbyle C¿6-22?, de préférence seulement avec présence minime de groupe hydrocarbyle C6-10 ou avec absence de celui-ci, et de préférence avec un indice d'iode allant d'environ 70 à environ 140, sur la base de l'indice d'iode de l'acide gras équivalent; n est un coefficient allant de 1 à 3 qui affecte la moyenne de poids dans tout mélange de composants; chaque R?1¿ présent dans un composé est un groupe alkyle C¿1-3? ou un groupe hydroxy alkyle, le total de n et le nombre de groupes R?1¿ qui sont des groupes hydroxyéthyle équivalant à 3, n+m valant 4; et X est un anion compatible avec un conditionneur, de préférence sulfate de méthyle. En l'occurrence, l'agent conditionneur a de préférence (a) une transmission 'L' de Hunter d'au moins 85 environ, (b) des niveaux non détectables, aux conditions d'utilisation, de composés odorants choisis entre acétate d'isopropyle, 2,2'-éthylidènebis(oxy)bispropane, et/ou esters d'acides gras du type court, ou (c) de préférence les deux. Par ailleurs, le niveau d'agent conditionneur renfermant des groupes alkylène polyinsaturé s'établit de préférence au moins environ à 3 %, en poids, par rapport à la quantité totale d'agent conditionneur présente et, enfin, l'agent conditionneur renferme de préférence un mélange de monoester et de diester. La composition renferme en outre (b) un émollient choisi entre: dérivés polyéthylène glycol de glycéride, éthers polypropylène et polyéthylène glycol de glucose, et éthers polypropylène glycol d'alcool gras, et des mélanges de ces produits. Le type de composition considéré offre d'excellentes propriétés quant au démêlage des cheveux ainsi qu'une sensation de propreté améliorée en état mouillé au rinçage et post-rinçage, permettant aussi de réduire au minimum la perte de volume.
PCT/US1999/014716 1998-06-29 1999-06-29 Composition pour le traitement des cheveux par conditionneur WO2000000174A1 (fr)

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001000169A1 (fr) * 1999-06-28 2001-01-04 The Procter & Gamble Company Compositions cosmetiques
WO2001000168A1 (fr) * 1999-06-28 2001-01-04 The Procter & Gamble Company Compositions cosmetiques
WO2003005985A1 (fr) * 2001-07-13 2003-01-23 The Procter & Gamble Company Compositions moussantes comprenant des agents d'ammonium quaternaire
FR2832057A1 (fr) * 2002-02-22 2003-05-16 Oreal Composition demaquillante
WO2003062360A1 (fr) * 2002-01-23 2003-07-31 The Procter & Gamble Company Auxiliaires de solubilite utilises dans des compositions detergentes
EP1495798A1 (fr) * 2003-07-01 2005-01-12 B & T S.r.l. Agent émulsifiant à base naturelle
US7209147B2 (en) 2001-03-15 2007-04-24 Kodak Polychrome Graphics Co. Ltd. Correction techniques for soft proofing
US7215343B2 (en) 2003-01-30 2007-05-08 Eastman Kodak Company Color correction using a device-dependent display profile
US8796217B2 (en) 2008-01-25 2014-08-05 HallStar Italia S.r.l. Use of transesterified olive oil in the cosmetic field
EP3692977A1 (fr) * 2019-02-08 2020-08-12 Kao Corporation Composition et procédé pour réduire le temps de séchage de substrats solides
WO2020160970A1 (fr) * 2019-02-08 2020-08-13 Kao Corporation Composition et procédé pour réduire le temps de séchage de substrats solides

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0655236A1 (fr) * 1993-11-26 1995-05-31 L'oreal Composition fondante contenant des sels d'ammonium quaternaire à fonction ester, son utilisation comme produit capillaire

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0655236A1 (fr) * 1993-11-26 1995-05-31 L'oreal Composition fondante contenant des sels d'ammonium quaternaire à fonction ester, son utilisation comme produit capillaire

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001000168A1 (fr) * 1999-06-28 2001-01-04 The Procter & Gamble Company Compositions cosmetiques
WO2001000169A1 (fr) * 1999-06-28 2001-01-04 The Procter & Gamble Company Compositions cosmetiques
US7209147B2 (en) 2001-03-15 2007-04-24 Kodak Polychrome Graphics Co. Ltd. Correction techniques for soft proofing
WO2003005985A1 (fr) * 2001-07-13 2003-01-23 The Procter & Gamble Company Compositions moussantes comprenant des agents d'ammonium quaternaire
US7033988B2 (en) 2002-01-23 2006-04-25 The Procter & Gamble Company Detergent tablets comprising solubility aids
WO2003062360A1 (fr) * 2002-01-23 2003-07-31 The Procter & Gamble Company Auxiliaires de solubilite utilises dans des compositions detergentes
FR2832057A1 (fr) * 2002-02-22 2003-05-16 Oreal Composition demaquillante
US7215343B2 (en) 2003-01-30 2007-05-08 Eastman Kodak Company Color correction using a device-dependent display profile
EP1495798A1 (fr) * 2003-07-01 2005-01-12 B & T S.r.l. Agent émulsifiant à base naturelle
US8097264B2 (en) 2003-07-01 2012-01-17 HallStar Italia S.r.l. Natural emulsifying agent
US8796217B2 (en) 2008-01-25 2014-08-05 HallStar Italia S.r.l. Use of transesterified olive oil in the cosmetic field
EP3692977A1 (fr) * 2019-02-08 2020-08-12 Kao Corporation Composition et procédé pour réduire le temps de séchage de substrats solides
WO2020160970A1 (fr) * 2019-02-08 2020-08-13 Kao Corporation Composition et procédé pour réduire le temps de séchage de substrats solides

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