US3829563A - Emollient cleansing compositions - Google Patents

Emollient cleansing compositions Download PDF

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Publication number
US3829563A
US3829563A US00311035A US31103572A US3829563A US 3829563 A US3829563 A US 3829563A US 00311035 A US00311035 A US 00311035A US 31103572 A US31103572 A US 31103572A US 3829563 A US3829563 A US 3829563A
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weight
percent
composition
component
hair
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P Orshitzer
R Barry
Matluck Meyer
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F Hoffmann La Roche AG
Richardson Vicks Inc
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F Hoffmann La Roche AG
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Priority to US00311035A priority Critical patent/US3829563A/en
Priority to DE2357335A priority patent/DE2357335A1/de
Priority to JP48132839A priority patent/JPS4981549A/ja
Priority to FR7342820A priority patent/FR2208644A1/fr
Priority to NL7316450A priority patent/NL7316450A/xx
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Publication of US3829563A publication Critical patent/US3829563A/en
Assigned to RICHARDSON-VICKS INC., 10 WESTPORT RD., WILTON, CT 06897, A CORP. OF DE reassignment RICHARDSON-VICKS INC., 10 WESTPORT RD., WILTON, CT 06897, A CORP. OF DE ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: HOFFMANN-LA ROCHE INC.
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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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/062—Oil-in-water emulsions
    • 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
    • A61K8/31—Hydrocarbons
    • 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
    • A61K8/42—Amides
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • 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
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8176—Homopolymers of N-vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/925—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of animal origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • 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
    • A61Q5/02—Preparations for cleaning the hair
    • 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

  • compositions which may be in a liquid or semi-solid form, are oil-in-water emulsions characterized by a particular particle size distribution of the oil phase and are comprised of from about 10 to about 70 percent by weight petrolatum, from about 5 to about 30 percent by weight of one or more organic foaming detergents, from about 1 to about 10 percent by weight of an emulsifier, from about 0.5 to about 5 percent weight of an organic foam stabilizer, from about 0 to about 20 percent by weight of one or more emollient substances other than petrolatum, and water.
  • the present invention relates to liquid or semi-solid compositions suitable for the cleansing and conditioning of the hair and skin.
  • conditioning is meant the deposition of a palpable emollient film on the hair and/or skin during the cleaning operation.
  • a palpable emollient film On the skin, such a film works to retard moisture loss from the epithelium and to maintain or restore the softness and smoothness of the skin surface.
  • the emollient film deposited by the novel preparations of this invention acts to impart combability and manageability thereto.
  • the aforementioned emollient film is comprised principally of petrolatum which may be supplemented by additional oily or fatty emollient substances such as are recognized in the art.
  • the present invention is concerned with the discovery that petrolatum can be formulated with certain organic detergents into oil-in-water emulsions which are unique in that they possess adequate foaming properties, cleanse exceptionally well and simultaneously deposit a film of fine particles of petrolatum on the skin or hair. This film, which acts to condition and soften the hair or skin, adheres sufficiently well thereto to remain after the latter is rinsed off with water.
  • the particle size distribution of the oil phase of the oil-in-water emulsions of the invention must be within certain limits for maximum physical stability and functional efficacy. Specifically, the great majority of these particles must be smaller than five microns for maximum stability of the emulsion. On the other hand, a minimal portion of the particles of the oil phase, i.e. petrolatum and other optional emollient substances, must be relatively large for functional efficacy. Therefore, the particles of the oil phase of the novel oilin-water emulsions of the invention have the following approximate distribution by size: up to about 98 percent are smaller than about five microns in their largest dimension: about 2 percent are five microns or larger and about 0.2 percent of the particles are 10 microns or larger.
  • the preferred particle size distribution by count is: from about to about 98 percent are smaller than five microns: from about 2 to about 5 percent are between five and 10 microns; from about 0.2 to about 1.0 percent are between 10 and 100 microns; and essentially none are larger than 100 microns at their largest dimension.
  • the above specified size distribution of the oil phase particles of the compositions of the invention can be achieved by continued agitation of the emulsion after formation. Such agitation is carried out at a temperature below 40C. i.e. from about 20 to about 40C., preferably from about 20 to about 30C. Agitation of the emulsion at these temperatures causes coalescence of the particles of the oil phase with a resultant increase in the mean or average size of such particles and an increase in the proportion by count of oil particles in the five to 100 micron size range.
  • the length of time required to achieve the desired particle size distribution will vary with the exact composition of the emulsion, the speed and type of equipment utilized, the batch size and the like. Generally, however, from about onefourth to 4 hours preferably about 2 hours is sufficient.
  • Increasing the proportion of oil phase particles in the five to 100 micron range increases the amount of oil phase particles deposited on skin or hair during use of the preparations of the invention for personal cleansing.
  • the particle size distribution of the oil phase may be determined by use of
  • compositions of the invention in general, comprise from about 10 to about 70 percent, preferably from about 10 to about 55 percent by weight of petrolatum; from about 5 to about 30 percent by weight, preferably from about 10 to about 30 percent by weight of one or more organic foaming detergents; from about 1 to about 10 percent by weight, preferably from about 3 to about 8 percent by weight of a suitable emulsifier; from about 0.5 to about 5 percent by weight, preferably from about 1 to about 3 percent by weight of an organic foam stabilizer; from about 0 to about 20 percent by weight, preferably from about 3 to about 15 percent by weight of one or more additional art-recognized emollient substances other than petrolatum and the remainder water.
  • compositions of the invention will vary depending on the desired consistency of the final product.
  • the compositions of the invention are oil-in-water emulsions, it is possible by varying the amount of water present to formulate, for example, a'thick-flowing liquid, a semiliquid thick creme, a paste and the like.
  • the compositions of the invention should not contain less than about 25 percent by weight nor more than about 80 percent by weight water if a liquid form is desired and not less than about percent by weight nor more than about 50 percent by weight of water where a paste preparation is desired.
  • the compositions preferably contain from about to about 50 percent by weight water wherein a paste composition is desired and from about 30 to about 80 percent by weight water where a liquid formulation is desired. In compositions containing from about 30 to about 50 percent by weight water, the consistency will vary between liquid and semi-solid depending on the characteristics of the non-aqueous ingredients.
  • the petrolatum suitable for use in the invention comprises any grade of white or yellow petrolatum which is recognized as being safe for application to the human skin or hair.
  • the preferred types are Petrolatum USP XVIII and NFXII.
  • any viscosity or consistency grade of petrolatum recognized in the art can be used in the invention. It is within the scope of the invention, however, to partially replace petrolatum with mixtures of hydrocarbon materials which can be formulated to resemble petrolatum in appearance and consistency.
  • such a combination can be formed by melting mineral oil in various proportions with substances such as, for example, microcrystalline wax, paraffin wax, ceresin and ozokerite.
  • compositions of the invention contain at least [0 percent petrolatum by weight.
  • Such additional emollient substances may be present in the compositions of the present invention up to about 20 percent by weight.
  • the synthetic organic foaming detergents utilized in the compositions of the invention may be of the anionic, non-ionic or amphoteric types.
  • An important consideration in the selection of a suitable detergent ingredient is the relative irritant properties of the individual detergents. Additional criteria to be met are the ability of each detergent to stabilize the emulsion, produce viscosity, achieve the desired foam level and remain stable at the pH level of the formulation, i.e. a pH of from about 7 to about 9.
  • suitable detergents include the following:
  • Anionic alkali and triethanolamine lauryl sulfates, lauryl ether sulfates, sodium alkylbenzene sulfonate, secondary alkyl sulfates, salts of higher acyl esters of isethionic acid, sodium salts of higher acyl derivatives of taurine or methyl taurine, alkyl phenol polyether sulfates, higher acyl derivatives of glycine and methylglycine, di-higher alkyl sulfosuccinates, higher alkyl alkanolamide ester sulfosuccinates, higher alkyl monoglyceride sulfates, alpha-olefin sulfonates;
  • Nonionic alkyl aryl polyether alcohols, alpha-hydro-omegahydroxy-poly (oxypropylene)polyoxyethylene block copolymers; and Amphoteric:
  • the preferred detergent ingredient in the compositions of the invention is a combination of about one part by weight of an alkali metal lauryl or lauryl ether sulfate and from about one-half to about 10 parts, preferably from about 1 to about 4 parts by weight of one or more disodium salts of higher alkyl substituted imidazolinium dicarboxylic acids such as, for example, the Miranol detergents which are manufactured by Miranol Chemical Co., Irvington, New Jersey and which have the following general formula X CHaCOONs wherein R is higher alkyl radical having, preferably, nine to 11 carbon atoms and X is an anion such as, for example, hydroxyl or lauryl sulfate.
  • These detergents when formulated into the compositions of the invention, yield the ideal balance of low irritation, quality and volume of foam and viscosity.
  • the detergent component of the compositions of the invention comprises from about 5 to about 30 percent by weight, preferably from about l0 to about 30 percent by weight thereof. In no instance, however, does the percent by weight of the detergent ingredient utilized exceed two times the percent by weightof the petrolatum present in the composition.
  • the emulsifiers suitable for use in the compositions of the invention include those amphiphilic organic emulsifiers recognized in the art as being safe for the type of products contemplated herein and of which the HLB values are from about 1 to about 19.
  • the preferred emulsifiers in accordance with the invention are those with HLB values of from about 1 to about 6. It is also within the practice of the invention to utilize more than one emulsifier the cumulative l-lLB value of which falls within the desired range.
  • emulsifiers examples include the following: sorbitan fatty acid esters, polyoxy-ethylene sorbitan fatty acid esters, polyoxyethylene sorbitol esters of fatty acids, lanolin, rosin, beeswax and tallow acids, polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, fatty acid monoand di-glycerides, polyglycerol fatty acid esters, polypropylene glycol fatty acid esters, fatty alcohol phosphate esters, polyethoxylated fatty alcohol phosphate esters and the like.
  • emulsifiers which are preferred in the practice of the invention include, for example, sorbitan monooleate, sorbitan sesquioleate, sorbitan trioleate, sorbitan monostearate, sorbitan tristearate, polyoxyethylene (2) oleyl ether, polyoxyethylene (2) stearyl ether, polyoxyethylene (2) cetyl ether, ethylene glycol monostearate, diethylene glycol oleate, diethylene glycol stearate, propylene glycol monostearate, propylene glycol distearate, glyceryl monostearate, glyceryl monooleate, decaglyceryl octaoleate, hexaglyceryl distearate and triglyceryl monooleate.
  • Suitable organic foam stabilizers which may additionally function as thickening agents in the compositions of the invention, include one or more of substances such as, for example, lauric, myristic and coconut oil fatty acid di-ethanolamides, monoethanolamides and isopropanolamides, stearyl trialkanol ammonium chlorides, fatty acid dimethylamine oxides, fatty acid diethanolamine oxides and the like.
  • substances such as, for example, lauric, myristic and coconut oil fatty acid di-ethanolamides, monoethanolamides and isopropanolamides, stearyl trialkanol ammonium chlorides, fatty acid dimethylamine oxides, fatty acid diethanolamine oxides and the like.
  • Preferred among this group are the coconut fatty acid diethanolamides wherein the fatty acids are predominantly l2 and 14 carbon atom acids, capric acid diethanolamide, lauric-myristic (70-30 monoethanolamide and stearyl trihydroxymethyl ammonium chloride.
  • emollient cleansing compositions thereof certain optional ingredients which are recognized as being conventional in the art for such preparations. These include, for example, organic or inorganic acids for pH adjustment, dyes, perfumes, preservatives, antioxidants, chelating agents and the like. Additionally, from about to about 3 percent by weight preferably from about 0.5 to about 1.5 percent by weight polyvinyl pyrrolidone may be included in the compositions of the invention for viscosity adjustment, and irritancy reduction. Oil soluble medicinal agents such as are recognized in the art for use in skin and hair cleansing preparations e.g. antidandruff agents, may also be included in the preparations of the invention to impart medicinal properties to the emollient film deposited on the skin or hair thereby.
  • compositions of the invention are prepared, generally, by first melting together all the fatty ingredients and combining the melt with agitation with the aqueous phase comprising a mixture of the detergents, the foam stabilizer and water, both phases being at a temperature of from about 60 to 80C.
  • the oily phase may be added to the aqueous phase or vice versa.
  • the mixture is then cooled to a temperature of below about 30C. with constant agitation.
  • Perfume ingredients are added to the mixture during the cooling process when the temperature thereof is at between 50 and 40C. After the temperature of the mixture has reached about 30C., the emulsion is observed under a microscope at 15 minute intervals while agitation is continued, and the temperature is maintained between 25 and 30C.
  • Agitation is continued until a substantial proportion, i.e. about 2 percent of the visible particles of the oil phase are larger than 5 microns, about 90 percent of said large particles being between 5 and microns and the remainder between about 10 and 100 microns.
  • a substantial proportion i.e. about 2 percent of the visible particles of the oil phase are larger than 5 microns, about 90 percent of said large particles being between 5 and microns and the remainder between about 10 and 100 microns.
  • the average particle size of the oil phase of the emulsion increases rapidly as the mixing time is extended and/or mixing speed increased.
  • the amount of oil phase deposited on the skin or hair during use of the compositions of the invention is directly related to the average particle size of the oil phase of the emulsion.
  • the oil deposition may be controlled within certain limits by the duration and speed of agitation during mixing of the emulsion at a temperature below about 30C. Washing tests on the skin and hair, as will be described hereinafter, may be utilized to determine standards whereby a termination point for the mixing may be determined.
  • the compositions of the invention should be agitated on conventional equipment while cooling to below 30C. such as, for example, by agitating with an anchor type stirrer running at 10-50 rpm for a period of from about one-half to about 4 hours, preferably about 2 hours.
  • the consistency of the product may be varied by adjusting the relative proportions of water, detergent, oil and thickener, and also by varying the melting point of the oil phase.
  • a water content of from about 20 to about 40 percent by weight will, in general, yield a product with the consistency of a thick paste whereas a water content above about 40 percent will yield products of increasing liquidity.
  • the foam volume produced by agitation with water may also be varied by varying the amount and kinds of foaming detergents utilized.
  • sodium lauryl sulfate possesses a large foam capacity but also a high irritancy. Its use in compositions of the type contemplated herein is thus limited.
  • compositions of the invention utilize at least 3 percent by weight, more preferably between about 5 and about 10 percent by weight sodium lauryl sulfate in combination with other foaming organic detergents which are lower in both foam production and irritancy.
  • a swatch of human hair about 8 inches long, of average fineness and weighing about 5 grams was tied together at one end and was cleansed by immersion in three 15 ml. portions of hexane, draining after each immersion. The hair was towel-dried and then allowed to completely dry in the air. The clean hair was thoroughly soaked in warm tap water, squeezed dry and treated with exactly 1 gram of the test composition which was spread over the swatch and worked vigorously with the fingers to produce maximum foam. After about one minute, the cleansing composition was removed by thoroughly rinsing the hair with warm tap water. The excess water was squeezed from the swatch and it was then dried with a towel, combed out and thoroughly dried in a current of hot air. The dried swatch was then exhaustively extracted with hexane. The extract was filtered through paper and evaporated to dryness. The oily residue was than accurately weighed and the milligrams of oil deposited per gram of product tested was calculated.
  • a rectangular area cm. X 10 cm. was marked along the flat, hairless, inner side of the forearm with a pencil. The arm was held so that the marked area was downward and a stream of hexane was sprayed on the area from a wash bottle until about 25 ml. was used. The hexane washings were then discarded. The dried, washed area, which appeared white and scaly, was then thoroughly wetted with water. Exactly 0.25 gram of test sample was distributed evenly over the test area. Using a little water, the composition was worked up to maximum lather by rubbing vigorously with the fingertips.
  • the arm was thoroughly rinsed with warm water until all slippery, soapy feel had disappeared from the test area which was then patted dry with a towel and allowed to dry in the air.
  • the treated area was then extracted with a stream of approximately 25 ml. of hexane collecting the drainings in a cm. diameter funnel held over a 50 ml. tared beaker.
  • the solvent was then evaporated and the weight of the oily residue determined and reported as mg. of oil deposited per gram of product tested.
  • EXAMPLE 1 A foaming emollient body cleanser for use in the bath or shower was prepared from the following formula.- tion:
  • the first five ingredients were combined and heated in a stainless container to about 80 with stirring.
  • the remaining ingredients were combined in a separate jacketed stainless steel kettle equipped with an anchor mixer and heated to about 80.
  • the sodium lauryl sulfate was added as a 42 percent aqueous paste and the imidazolinium salt was added as a 38 percent aqueous solution.
  • the oil phase was then added slowly to the aqueous phase while mixing rapidly (about 2,000 rpm) with an inserted impeller mixer. After incorporation and emulsification of the oil were complete, the impeller was removed and mixing was continued by anchor blade rotating at about 30 rpms. The temperature of the emulsion was lowered to 50 by cold water circulating through the kettle jacket.
  • the perfume was added and the temperature of the emulsion was then gradually lowered to 30. Mixing was continued for an additional two hours during which the temperature of the emulsion cooled to about 25. Stirring was continued until microscopic observation of the emulsion at magnifications indicated proper particle size distribution. Stirring was then discontinued and the product was packaged into suitable containers.
  • the product was a stable, opaque, viscous yet pourable lotion. When applied to the skin and lathered with water it provided very good foam quality. When tested on the skin of the forearm as described, the product deposited about 30 mg. of oil per gram applied and the skin surface felt soft and supple.
  • this preparation As this preparation is to be applied to the face, the pH was adjusted downward to about 7.2 to minimize eye-sting and irritancy. Likewise, the oil content of this preparation was made higher than the preparation of Example 1 to facilitate removal of makeup and to deposit a heavier oil film on the face to combat dry skin.
  • the preparation was a soft cream which produced a moderate lather and deposited a perceptible film on the skin. In the forearm test described herein, the product was found to deposit about 40 mg. of oil per gram applied and leave the skin soft and supple.
  • EXAMPLE 3 A grooming and conditioning shampoo for mens hair was prepared from the following formulation in accordance with the method of claim 1.
  • Hair washed with the preparation did not have the squeaky feel commonly experienced with currently available soaps or shampoos but instead was smooth and, after drying, had a light dressed appearance without feeling or looking oily or greasy.
  • the product was found by the hair test described herein to deposit about 30 mg. of oil per gram.
  • EXAMPLE 4 A conditioning shampoo for womens hair was prepared in accordance with the method of claim-1 from the following formulation:
  • the product provided good foam and excellent conditioning properties. Hair washed with this composition was free from squeakiness and combed out with little or no tangling. There was no need to treat the hair with an after-shampoo conditioning agent except in some exceptional cases. The dry hair had good gloss, body and hold and was free of frizziness and excessive flyaway.
  • the product, a soft, stable creme provided a lighter dressing or grooming effect (10 mg. of oil per gram by the hair test described herein) than the mens shampoo of Example 3 in keeping with the softer finish preferred by women.
  • a foaming, emollient composition suitable for the cleansing of the skin and hair consisting essentially of an oil-in-water emulsion wherein from about 95 to about 98 percent of the particles of the oil phase thereof are smaller than about 5 microns at their largest dimension, from about 2 to about 5 percent of said particles are from about 5 microns to about microns at their largest dimension, from about 0.2 to about 1.0 percent of said particles are between about 10 microns and 100 microns at their largest dimension and substantially no particles are greater than 100 microns at their largest dimension, said emulsion comprising:
  • an organic foaming detergent component comprising a mixture of one part by weight sodium lauryl sulfate and from about one-half to about 10 parts by weight of one or more amphoteric detergents selected from those represented by the formula i ⁇ X CHr-C OONa wherein R is an alkyl radical containing from nine to 11 carbon atoms and X is hydroxyl or lauryl sulfate;
  • an emulsifier component having an HLB value of from 1 to 6 and selected from the group consisting of sorbitan monooleate, sorbitan sesquioleate, sorbitan trioleate, sorbitan monostearate, sorbitan tristearate, polyoxyethylene (2) oleyl ether, polyoxyethylene (2) stearyl ether, polyoxyethylene (2) cetyl ether, ethylene glycol monostearate, diethylene glycol oleate, diethylene glycol stearate, propylene glycol monostearate, propylene glycol distearate, glyceryl monostearate, glyceryl monooleate, decaglyceryl octaoleate, hexaglyceryl distearate and triglyceryl monooleate;
  • an organic foam stabilizer selected from the group consisting of capric acid diethanolamide, stearyl trihydroxymethyl ammonium chloride and lauric-myristic (70-30) monoethanolamide;
  • composition in accordance with claim 1 wherein said component a a) is present in from about 10 to about 55 percent by weight, said component b) is present in from about 10 to about 30 percent by weight, saidcomponent 0) is present in from about 3 to about 8 percent by weight and said component d) is present in from about 1 to about 3 percent by weight.
  • composition in accordance with claim 1 wherein said component b) comprises one part by weight sodium lauryl sulfate and from about 1 to about 4 parts by weight of one or more of said amphoteric detergents.
  • composition in accordance with claim 1 additionally containing from about 0.5 by weight to about 1.5 percent by weight poly-vinylpyrrolidone.
  • a method of preparing a foaming emollient composition suitable for the cleansing of the skin and hair said composition comprising:
  • an organic foaming detergent component comprising a mixture of one part by weight sodium lauryl sulfate and from about one-half to about parts by weight of one or more amphoteric detergents selected from those represented by the formula wherein R is an alkyl radical containing from 9 to 11 carbon atoms and X is hydroxyl or lauryl sulfate;
  • an emulsifier component having an HLB value of from 1 to 6 and selected from the group consisting of sorbitan monooleate, sorbitan sesquioleate, sorbitan trioleate, sorbitan monostearate, sorbitan tristearate, polyoxyethylene (2) oleyl ether, polyoxyethylene (2) stearyl ether, polyoxyethylene (2) cetyl ether, ethylene glycol monostearate, diethylene glycol oleate, diethylene glycol stearate, propylene glycol monostearate, propylene glycol distearate, glyceryl monostearate, glyceryl monooleate, decaglyceryl octaoleate, hexaglyceryl distearate and triglyceryl monooleate;
  • an organic foam stabilizer selected from the group consisting of capric acid diethanolamide, stearyl trihydroxymethyl ammonium chloride and lauric-myristic (-30) monoethanolamide;

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
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US00311035A 1972-11-30 1972-11-30 Emollient cleansing compositions Expired - Lifetime US3829563A (en)

Priority Applications (5)

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US00311035A US3829563A (en) 1972-11-30 1972-11-30 Emollient cleansing compositions
DE2357335A DE2357335A1 (de) 1972-11-30 1973-11-16 Kosmetisches praeparat
JP48132839A JPS4981549A (enrdf_load_stackoverflow) 1972-11-30 1973-11-28
FR7342820A FR2208644A1 (enrdf_load_stackoverflow) 1972-11-30 1973-11-30
NL7316450A NL7316450A (enrdf_load_stackoverflow) 1972-11-30 1973-11-30

Applications Claiming Priority (1)

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US00311035A US3829563A (en) 1972-11-30 1972-11-30 Emollient cleansing compositions

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US3829563A true US3829563A (en) 1974-08-13

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US (1) US3829563A (enrdf_load_stackoverflow)
JP (1) JPS4981549A (enrdf_load_stackoverflow)
DE (1) DE2357335A1 (enrdf_load_stackoverflow)
FR (1) FR2208644A1 (enrdf_load_stackoverflow)
NL (1) NL7316450A (enrdf_load_stackoverflow)

Cited By (51)

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US4078055A (en) * 1975-04-11 1978-03-07 Kao Soap Co., Ltd. Deodorizing and smell-removing composition and method of using same
US4112167A (en) * 1977-01-07 1978-09-05 The Procter & Gamble Company Skin cleansing product having low density wiping zone treated with a lipophilic cleansing emollient
US4126674A (en) * 1976-05-11 1978-11-21 Helena Rubinstein, Inc. Thickened aqueous shampoo compositions containing encapsulated conditioning agents
US4306997A (en) * 1976-01-16 1981-12-22 Lever Brothers Company Foam bath compositions containing anionic detergent and monoglyceride
US4310516A (en) * 1980-02-01 1982-01-12 Block Drug Company Inc. Cosmetic and pharmaceutical vehicle thickened with solid emulsifier
US4438096A (en) 1982-05-27 1984-03-20 Helene Curtis Industries, Inc. Pearlescent shampoo
US4495079A (en) * 1983-04-21 1985-01-22 Good Allen H Facial skin cleanser capable of softening and removing sebum plaque
US4777038A (en) * 1985-05-28 1988-10-11 Henkel Kommanditgesellschaft Auf Aktien Free-flowing pearlescent concentrate
US4808322A (en) * 1988-03-10 1989-02-28 Mclaughlin James H Skin cleansing-cream conditioning bar
US4941990A (en) * 1988-03-10 1990-07-17 Mclaughlin James H Skin cleansing-cream conditioning bar
WO1993019149A1 (en) * 1992-03-25 1993-09-30 The Procter & Gamble Company Cleansing compositions
US5254334A (en) * 1992-05-04 1993-10-19 Imaginative Research Associates, Inc. Anhydrous foaming composition containing low concentrations of detergents and high levels of glycerin amd emollients such as oils and esters
US5308526A (en) * 1992-07-07 1994-05-03 The Procter & Gamble Company Liquid personal cleanser with moisturizer
US5312559A (en) * 1992-07-07 1994-05-17 The Procter & Gamble Company Personal cleanser with moisturizer
US5409706A (en) * 1992-05-04 1995-04-25 Imaginative Research Associates, Inc. Anhydrous foaming composition containing low concentrations of detergents and high levels of glycerin and emollients such as oils and esters
US5547602A (en) * 1995-05-12 1996-08-20 The Broxon Marketing Group, Inc. Moisturizing soap bar
US5562912A (en) * 1994-06-10 1996-10-08 Basf Corporation Liquid skin cleanser composition with reduced skin irritation and improved after-feel
US5674511A (en) * 1994-12-06 1997-10-07 The Procter & Gamble Company Shelf stable skin cleansing liquid with gel forming polymer, lipid and crystalline ethylene glycol fatty acid ester
US5693255A (en) * 1993-03-15 1997-12-02 Shiseido Co., Ltd. Oil-in-water type emulsion composition
US5776872A (en) * 1992-03-25 1998-07-07 The Procter & Gamble Company Cleansing compositions technical field
US5804540A (en) * 1997-01-08 1998-09-08 Lever Brothers Company, Division Of Conopco, Inc. Personal wash liquid composition comprising low viscosity oils pre-thickened by non-antifoaming hydrophobic polymers
US5854293A (en) * 1996-09-23 1998-12-29 The Procter & Gamble Company Liquid personal cleansing composition which contain a lipophilic skin moisturizing agent comprised of relatively large droplets
US5869071A (en) * 1996-11-07 1999-02-09 B & G Labs, Inc. One-step skin cleaning composition and skin treatment method for incontinent dermatitis
US5869070A (en) * 1994-12-06 1999-02-09 The Procter & Gamble Company Shelf stable skin cleansing liquid with gel forming polymer and lipid
US5885948A (en) * 1995-02-15 1999-03-23 The Procter & Gamble Company Crystalline hydroxy waxes as oil in water stabilizers for skin cleansing liquid composition
US5965500A (en) * 1997-07-24 1999-10-12 Levers Brothers Company, Division Of Conopco, Inc. Stable liquid composition comprising high levels of emollients
US6063746A (en) * 1995-08-14 2000-05-16 The Procter & Gamble Company Cleansing preparation
US6066608A (en) * 1996-09-23 2000-05-23 The Procter & Gamble Company Liquid personal cleansing composition which contain a lipophilic skin moisturing agent comprised of relatively large droplets
US6077816A (en) * 1995-08-07 2000-06-20 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Liquid cleansing composition comprising soluble, lamellar phase inducing structurant
US6080707A (en) * 1995-02-15 2000-06-27 The Procter & Gamble Company Crystalline hydroxy waxes as oil in water stabilizers for skin cleansing liquid composition
US6136765A (en) * 1995-03-14 2000-10-24 The Procter & Gamble Company Dispersed smectite clay as oil in water stabilizer for skin cleansing liquid composition
US6277797B1 (en) 1995-03-14 2001-08-21 The Procter & Gamble Company Dispersed amorphous silica as oil in water stabilizer for skin cleansing liquid composition
WO2002100295A3 (en) * 2001-03-08 2003-05-01 Univ Pennsylvania Facially amphiphilic polymers as anti-infective agents
US6586479B2 (en) * 2000-07-21 2003-07-01 Clariant Gmbh Process for preparing fine emulsions
US20050239669A1 (en) * 2004-04-22 2005-10-27 Kimberly-Clark Worldwide, Inc. Liquid cleanser compositions
US20050287108A1 (en) * 2004-01-23 2005-12-29 Degrado William F Facially amphiphilic polyaryl and polyarylalkynyl polymers and oligomers and uses thereof
US20060041023A1 (en) * 2003-03-17 2006-02-23 The Trustees Of The University Of Pennsylvania Facially amphilic polymers and oligomers and uses thereof
US20060104912A1 (en) * 1998-09-11 2006-05-18 Connetics Australia Pty Ltd Mousse composition
US20060241052A1 (en) * 2005-02-25 2006-10-26 Degrado William F Facially amphiphilic polymers and oligomers, compositions thereof, and use thereof in methods of treating cancer
US20060292080A1 (en) * 1998-09-11 2006-12-28 Connetics Australia Pty Ltd Vitamin formulation
US7211552B1 (en) * 2002-11-13 2007-05-01 Melton Sherwood Thoele Enzymatic detergent
EP1673055A4 (en) * 2003-10-15 2007-08-08 Cognis Ip Man Gmbh PLANT SUBSTITUTE OF LANOLINE
EP1496855A4 (en) * 2002-04-19 2007-08-08 Cognis Ip Man Gmbh PLANT SUBSTITUTE OF LANOLINE
US20110014135A1 (en) * 2005-06-01 2011-01-20 Stiefel Research Australia Pty Ltd Vitamin formulation
US20130272987A1 (en) * 2012-04-16 2013-10-17 Conopco, Inc., D/B/A Unilever Pre-Blended Mixtures of Specific Hydrocarbon Liquids Structured with High Melting Point Structuring Material
US20150322388A1 (en) * 2012-12-07 2015-11-12 Colgate-Palmolive Company Bar Soap Composition and Method of Manufacture
US9655821B2 (en) 2013-04-05 2017-05-23 The Procter & Gamble Company Personal care composition comprising a pre-emulsified formulation
US9993404B2 (en) 2015-01-15 2018-06-12 The Procter & Gamble Company Translucent hair conditioning composition
US10806688B2 (en) 2014-10-03 2020-10-20 The Procter And Gamble Company Method of achieving improved volume and combability using an anti-dandruff personal care composition comprising a pre-emulsified formulation
US10912723B2 (en) 2016-01-20 2021-02-09 The Procter And Gamble Company Hair conditioning composition comprising monoalkyl glyceryl ether
US11123362B2 (en) * 2015-12-28 2021-09-21 Alumend, Llc Compositions and methods to affect skin irritation

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CA1138292A (en) * 1978-06-30 1982-12-28 Johannes C.P. Schreuder Handwashing composition
LU83020A1 (fr) * 1980-12-19 1982-07-07 Oreal Composition huileuse destinee au traitement des matieres keratiniques et de la peau
CA1202861A (en) * 1981-11-12 1986-04-08 Joseph R. Ehrlich Bubble composition using multi-purpose surfactant base
FR2580493B1 (fr) * 1985-04-23 1988-06-10 Oreal Composition cosmetique de nettoyage, en particulier pour le demaquillage des yeux
GB9200764D0 (en) * 1992-01-15 1992-03-11 Unilever Plc Cosmetic composition
FR2745175A1 (fr) * 1996-02-26 1997-08-29 Rhone Poulenc Chimie Composition cosmetique capillaire et procedes de preparation
DE10010768A1 (de) * 2000-03-04 2001-09-06 Clariant Gmbh Wäßrige oder wäßrig-alkoholische Körperreinigungsmittel enthaltend Sorbitolester
US8772212B2 (en) * 2008-08-07 2014-07-08 Conopco, Inc. Liquid personal cleansing composition

Cited By (71)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4078055A (en) * 1975-04-11 1978-03-07 Kao Soap Co., Ltd. Deodorizing and smell-removing composition and method of using same
US4306997A (en) * 1976-01-16 1981-12-22 Lever Brothers Company Foam bath compositions containing anionic detergent and monoglyceride
US4126674A (en) * 1976-05-11 1978-11-21 Helena Rubinstein, Inc. Thickened aqueous shampoo compositions containing encapsulated conditioning agents
US4112167A (en) * 1977-01-07 1978-09-05 The Procter & Gamble Company Skin cleansing product having low density wiping zone treated with a lipophilic cleansing emollient
US4310516A (en) * 1980-02-01 1982-01-12 Block Drug Company Inc. Cosmetic and pharmaceutical vehicle thickened with solid emulsifier
US4438096A (en) 1982-05-27 1984-03-20 Helene Curtis Industries, Inc. Pearlescent shampoo
US4495079A (en) * 1983-04-21 1985-01-22 Good Allen H Facial skin cleanser capable of softening and removing sebum plaque
US4777038A (en) * 1985-05-28 1988-10-11 Henkel Kommanditgesellschaft Auf Aktien Free-flowing pearlescent concentrate
US4808322A (en) * 1988-03-10 1989-02-28 Mclaughlin James H Skin cleansing-cream conditioning bar
US4941990A (en) * 1988-03-10 1990-07-17 Mclaughlin James H Skin cleansing-cream conditioning bar
WO1993019149A1 (en) * 1992-03-25 1993-09-30 The Procter & Gamble Company Cleansing compositions
US5776872A (en) * 1992-03-25 1998-07-07 The Procter & Gamble Company Cleansing compositions technical field
US5254334A (en) * 1992-05-04 1993-10-19 Imaginative Research Associates, Inc. Anhydrous foaming composition containing low concentrations of detergents and high levels of glycerin amd emollients such as oils and esters
US5409706A (en) * 1992-05-04 1995-04-25 Imaginative Research Associates, Inc. Anhydrous foaming composition containing low concentrations of detergents and high levels of glycerin and emollients such as oils and esters
US5308526A (en) * 1992-07-07 1994-05-03 The Procter & Gamble Company Liquid personal cleanser with moisturizer
US5312559A (en) * 1992-07-07 1994-05-17 The Procter & Gamble Company Personal cleanser with moisturizer
US5496488A (en) * 1992-07-07 1996-03-05 The Procter & Gamble Company Cleansing bar composition containing petrolatum having a specific size range
US5693255A (en) * 1993-03-15 1997-12-02 Shiseido Co., Ltd. Oil-in-water type emulsion composition
US5562912A (en) * 1994-06-10 1996-10-08 Basf Corporation Liquid skin cleanser composition with reduced skin irritation and improved after-feel
US5674511A (en) * 1994-12-06 1997-10-07 The Procter & Gamble Company Shelf stable skin cleansing liquid with gel forming polymer, lipid and crystalline ethylene glycol fatty acid ester
US5869070A (en) * 1994-12-06 1999-02-09 The Procter & Gamble Company Shelf stable skin cleansing liquid with gel forming polymer and lipid
US6080707A (en) * 1995-02-15 2000-06-27 The Procter & Gamble Company Crystalline hydroxy waxes as oil in water stabilizers for skin cleansing liquid composition
US5885948A (en) * 1995-02-15 1999-03-23 The Procter & Gamble Company Crystalline hydroxy waxes as oil in water stabilizers for skin cleansing liquid composition
US6277797B1 (en) 1995-03-14 2001-08-21 The Procter & Gamble Company Dispersed amorphous silica as oil in water stabilizer for skin cleansing liquid composition
US6136765A (en) * 1995-03-14 2000-10-24 The Procter & Gamble Company Dispersed smectite clay as oil in water stabilizer for skin cleansing liquid composition
US5547602A (en) * 1995-05-12 1996-08-20 The Broxon Marketing Group, Inc. Moisturizing soap bar
US6077816A (en) * 1995-08-07 2000-06-20 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Liquid cleansing composition comprising soluble, lamellar phase inducing structurant
US6300301B1 (en) 1995-08-14 2001-10-09 The Procter & Gamble Company Cleansing preparation and articles comprising a cleansing preparation
US6063746A (en) * 1995-08-14 2000-05-16 The Procter & Gamble Company Cleansing preparation
US6066608A (en) * 1996-09-23 2000-05-23 The Procter & Gamble Company Liquid personal cleansing composition which contain a lipophilic skin moisturing agent comprised of relatively large droplets
US5854293A (en) * 1996-09-23 1998-12-29 The Procter & Gamble Company Liquid personal cleansing composition which contain a lipophilic skin moisturizing agent comprised of relatively large droplets
US5869071A (en) * 1996-11-07 1999-02-09 B & G Labs, Inc. One-step skin cleaning composition and skin treatment method for incontinent dermatitis
US5804540A (en) * 1997-01-08 1998-09-08 Lever Brothers Company, Division Of Conopco, Inc. Personal wash liquid composition comprising low viscosity oils pre-thickened by non-antifoaming hydrophobic polymers
US5965500A (en) * 1997-07-24 1999-10-12 Levers Brothers Company, Division Of Conopco, Inc. Stable liquid composition comprising high levels of emollients
US20060104912A1 (en) * 1998-09-11 2006-05-18 Connetics Australia Pty Ltd Mousse composition
US8263580B2 (en) 1998-09-11 2012-09-11 Stiefel Research Australia Pty Ltd Vitamin formulation
US20060292080A1 (en) * 1998-09-11 2006-12-28 Connetics Australia Pty Ltd Vitamin formulation
US6586479B2 (en) * 2000-07-21 2003-07-01 Clariant Gmbh Process for preparing fine emulsions
US7173102B2 (en) 2001-03-08 2007-02-06 The Trustees Of The University Of Pennsylvania Facially amphiphilic polymers as anti-infective agents
US20040202639A1 (en) * 2001-03-08 2004-10-14 Degrado William F. Facially amphiphilic polymers as anti-infective agents
US8889163B2 (en) 2001-03-08 2014-11-18 The Trustees Of The University Of Pennsylvania Facially amphiphilic polymers as anti-infective agents
US20040185257A1 (en) * 2001-03-08 2004-09-23 Degrado William F. Facially amphiphilic polymers as anti-infective agents
KR100904284B1 (ko) * 2001-03-08 2009-06-25 더 트러스티스 오브 더 유니버시티 오브 펜실베니아 항-감염제로서의 표면적 친양쪽성 중합체
WO2002100295A3 (en) * 2001-03-08 2003-05-01 Univ Pennsylvania Facially amphiphilic polymers as anti-infective agents
EP1496855A4 (en) * 2002-04-19 2007-08-08 Cognis Ip Man Gmbh PLANT SUBSTITUTE OF LANOLINE
US7211552B1 (en) * 2002-11-13 2007-05-01 Melton Sherwood Thoele Enzymatic detergent
US9241917B2 (en) 2003-03-17 2016-01-26 The Trustees Of The University Of Pennsylvania Facially amphiphilic polymers and oligomers and uses thereof
US20060041023A1 (en) * 2003-03-17 2006-02-23 The Trustees Of The University Of Pennsylvania Facially amphilic polymers and oligomers and uses thereof
US8236800B2 (en) 2003-03-17 2012-08-07 The Trustees Of The University Of Pennsylvania Facially amphiphilic polymers and oligomers and uses thereof
US8455490B2 (en) 2003-03-17 2013-06-04 The Trustees Of The University Of Pennsylvania Facially amphiphilic polymers and oligomers and uses thereof
US20080176807A1 (en) * 2003-03-17 2008-07-24 Degrado William F Facially amphiphilic polymers and oligomers and uses thereof
EP1673055A4 (en) * 2003-10-15 2007-08-08 Cognis Ip Man Gmbh PLANT SUBSTITUTE OF LANOLINE
US8716530B2 (en) 2004-01-23 2014-05-06 The Trustess Of The University Of Pennsylvania Facially amphiphilic polyaryl and polyarylalkynyl polymers and oligomers and uses thereof
US20050287108A1 (en) * 2004-01-23 2005-12-29 Degrado William F Facially amphiphilic polyaryl and polyarylalkynyl polymers and oligomers and uses thereof
US8222456B2 (en) 2004-01-23 2012-07-17 The Trustees Of The University Of Pennsylvania Facially amphiphilic polyaryl and polyarylalkynyl polymers and oligomers and uses thereof
US7666824B2 (en) * 2004-04-22 2010-02-23 Kimberly-Clark Worldwide, Inc. Liquid cleanser compositions
US20050239669A1 (en) * 2004-04-22 2005-10-27 Kimberly-Clark Worldwide, Inc. Liquid cleanser compositions
US20060241052A1 (en) * 2005-02-25 2006-10-26 Degrado William F Facially amphiphilic polymers and oligomers, compositions thereof, and use thereof in methods of treating cancer
US8298515B2 (en) 2005-06-01 2012-10-30 Stiefel Research Australia Pty Ltd. Vitamin formulation
US20110014135A1 (en) * 2005-06-01 2011-01-20 Stiefel Research Australia Pty Ltd Vitamin formulation
US8629128B2 (en) 2005-06-01 2014-01-14 Stiefel West Coast, Llc Vitamin formulation
US20130272987A1 (en) * 2012-04-16 2013-10-17 Conopco, Inc., D/B/A Unilever Pre-Blended Mixtures of Specific Hydrocarbon Liquids Structured with High Melting Point Structuring Material
CN104302270A (zh) * 2012-04-16 2015-01-21 荷兰联合利华有限公司 用高熔点结构化材料结构化的特定烃液体的预混混合物
US9809788B2 (en) * 2012-12-07 2017-11-07 Colgate-Palmolive Company Bar soap composition and method of manufacture
US20150322388A1 (en) * 2012-12-07 2015-11-12 Colgate-Palmolive Company Bar Soap Composition and Method of Manufacture
US9655821B2 (en) 2013-04-05 2017-05-23 The Procter & Gamble Company Personal care composition comprising a pre-emulsified formulation
US10806688B2 (en) 2014-10-03 2020-10-20 The Procter And Gamble Company Method of achieving improved volume and combability using an anti-dandruff personal care composition comprising a pre-emulsified formulation
US9993404B2 (en) 2015-01-15 2018-06-12 The Procter & Gamble Company Translucent hair conditioning composition
US11123362B2 (en) * 2015-12-28 2021-09-21 Alumend, Llc Compositions and methods to affect skin irritation
US11135241B2 (en) * 2015-12-28 2021-10-05 Alumend, Llc Compositions and methods to affect skin irritation
US10912723B2 (en) 2016-01-20 2021-02-09 The Procter And Gamble Company Hair conditioning composition comprising monoalkyl glyceryl ether

Also Published As

Publication number Publication date
NL7316450A (enrdf_load_stackoverflow) 1974-06-04
DE2357335A1 (de) 1974-06-06
FR2208644A1 (enrdf_load_stackoverflow) 1974-06-28
JPS4981549A (enrdf_load_stackoverflow) 1974-08-06

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Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:HOFFMANN-LA ROCHE INC.;REEL/FRAME:004134/0481

Effective date: 19830128