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WO1994010973A1 - Composition cosmetique - Google Patents

Composition cosmetique Download PDF

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Publication number
WO1994010973A1
WO1994010973A1 PCT/EP1993/003097 EP9303097W WO9410973A1 WO 1994010973 A1 WO1994010973 A1 WO 1994010973A1 EP 9303097 W EP9303097 W EP 9303097W WO 9410973 A1 WO9410973 A1 WO 9410973A1
Authority
WO
WIPO (PCT)
Prior art keywords
gel composition
composition according
layered double
double hydroxide
general structure
Prior art date
Application number
PCT/EP1993/003097
Other languages
English (en)
Inventor
Kevin Ronald Franklin
Jacqueline Diane Hewitt-Jones
Original Assignee
Unilever Plc
Unilever Nv
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Unilever Plc, Unilever Nv filed Critical Unilever Plc
Priority to AU54207/94A priority Critical patent/AU5420794A/en
Publication of WO1994010973A1 publication Critical patent/WO1994010973A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides 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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/042—Gels
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • 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
    • A61K8/927—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of insects, e.g. shellac
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings

Definitions

  • the invention relates to a novel cosmetic composition, which has surprising occlusivity, which can be applied topically to the human body surface, especially the skin (including the mucosae) , hair and nails.
  • Hydrocarbons such as petrolatum (also known as petroleum jelly or soft paraffin) have been used for many years for topical application to human skin for providing an occlusive film thereon to prevent water loss to the environment, thereby allowing water diffusing from the underlying tissues to accumulate in the stratum corneum.
  • Petrolatum has also been used as an ingredient of skin care products, such as hand creams and lotions, and has also featured in hair grooming or conditioning products, particularly as a setting aid to maintain hair in a desired configuration.
  • petrolatum possesses a relatively narrow spectrum of sensory or aesthetic properties.
  • it can impart to the skin and hair an uncomfortable feeling of warmth, in addition to a sticky, waxy feel, and this has restricted its use to barrier products such as petrolatum itself and hand creams containing it, where a temporary functional protective film on the skin is desired, and to hair dressings such as pomades.
  • petrolatum is derived from fossil fuels, whose supply is non-renewable.
  • disadvantages such as those attributable to traditional petrolatum, there exists a need to locate an alternative occlusive product that has all the desirable attributes of emolliency and occlusivity of petrolatum, without serious negative subjective properties.
  • an alternative product ideally should contain a major proportion of plant-derived material to suit environmental, ecological and personal health care needs.
  • the lipophilic organic compound used is a desired vegetable oil
  • the gel composition has negligable occlusivity.
  • an occlusive gel composition comprising
  • A is a calcium, zinc or magnesium ion
  • B is an interlayer anion y is a charge on the anion x is 0.1 to 0.5 z is 0 to 100
  • n is an integer of from 6 to 20 and is an integer of from 1 to 6;
  • the gel composition according to the invention in its simplest form, comprises of a layered double hydroxide, a vegetable oil that is liquid at room temperature and a secondary thickener that is solid at room temperature.
  • This composition has desirable occlusive properties.
  • the gel composition so formed will generally retain its gel-like characteristics over a wide temperature range for example from -15°C to +60°C.
  • x is preferably 0.15 to 0.4; more preferably 0.25 to 0.35 and z is preferably 0 to 4, more preferably 0 to 1.
  • interlayer anion (B) is selected from monocarboxylate, mono alkyl sulphate, monoalkyl ether sulphate, alkyl benzene sulphonate or mixtures thereof, the respective structure being as defined by structures (2) , (3) , (4) and (5) .
  • the interlayer anion (B) is a monocarboxylic acid having the general structure (2) .
  • the remaining interlayer anion component may be any inorganic or organic anion. Preferred are nitrate, carbonate, sulphate, chloride, citrate, benzoate and mixtures thereof.
  • gel compositions according to the invention comprise 1 to 40 wt%, more preferably 5 to 40 wt% and even more preferably 15 to 40 wt % of the layered double hydroxide.
  • the layered double hydroxides may be prepared by several methods. Not wishing to preclude other routes, they may be precipitated from a solution containing a mixture of zinc/calcium/magnesium and aluminium salts (for example nitrates, chlorides, sulphates) by addition of sodium hydroxide or a similar base as detailed by Thevenot et al (Clays and Clay Minerals (1989) 5 396) or by direct reaction of a zinc/calcium/magnesium oxide slurry with an aluminium salt solution. The crystallinity and crystal size of the product may subsequently be increased by ageing the layered double hydroxide in its ⁇ upernatent at temperatures up to 200°C.
  • a mixture of zinc/calcium/magnesium and aluminium salts for example nitrates, chlorides, sulphates
  • Moncarboxylate, suphonate, alkyl sulphate or alkyl ether sulphate ions may be introduced into the layered double hydroxide by ion exchange or using the partial decomposition-reformation procedure described by Dimotakis and Pinnavaia (Inorganic Chemistry (1990) 13 , 2393) .
  • the crystal size is small since smaller crystals provide better thickening properties. Especially preferred are crystals having a plate diameter of less than 0.2 ⁇ n.
  • the Zn/Al ratio was found by XRF analysis to be 2.0.
  • the water content was determined by thermal analysis and is consistent with the molar composition.
  • the water is labile and may vary slightly with storage.
  • TEM shows the crystals to be stacks of hexagonal plates of about 0.2/tm diameter.
  • a solution of potassium laurate was first prepared by dissolving 28.43g of lauric acid and 8.34g of potassium hydroxide in 700ml of water and heating to about 70°C. 50g of Zn/Al hydroxy nitrate, prepared according to the method above, was placed in a 11 polypropylene bottle and the potassiuim laurate solution was added. The bottle was capped, shaken for 2 minutes and then placed in a thermostated oven at 90°C for 18 hrs. The solid was filtered off, washed thoroughly with hot water, and freeze dried. The material was finally equilibrated with water vapour at a water activity of 0.75.
  • MgO magnesium oxide
  • A1(N0 3 ) 3 .9H 2 0 aluminium nitrate
  • the Mg/Al ratio was found by XRF analysis to be 2.0.
  • the water content was determined by thermal analysis and is consistent with the molar composition.
  • the water is labile and may vary slightly with storage.
  • TEM shows the crystals to be stacks of hexagonal plates of about O.O ⁇ m diameter.
  • Carboxylate Decanoate, Laurate, Myristate, Palmitate, Stearate.
  • a solution of potassium carboxylate was first prepared by dissolving appropriate amount of carboxylic acid (see table below) and 10.61g of potassium hydroxide in 700ml of water and heating to about 70°C. 50g of Mg/Al hydroxy nitrate, prepared according to the method above, were placed in a IL polypropylene bottle and the potassium carboxylate solution was added. The bottle was capped, shaken for 2 minutes and then placed in a thermostated oven at 90°C for 18 hrs. The solid was filtered off, washed thoroughly with hot water, and freeze dried. The material was finally equilibrataed with water vapour at a water activity of 0.75.
  • the basal spacing of the product (from XRD) is also given in the table.
  • the basal spacing of the product (from XRD) was 19.5A.
  • Suitable compounds are liquid at room temperature (20°C) .
  • the vegetable oil may be chosen from:
  • gel compositions according to the invention comprise 50 to 90 wt % of the composition, more preferably 60 to 80 wt % of the composition and even more preferably 70 wt % of the composition of the vegetable oil.
  • the secondary thickener is solid at room temperature. Such secondary thickeners must also be compatible with, and able to form some structure in, the lipophillic organic compound disclosed above.
  • Preferred secondary thickeners may be selected from plant and animal fats, waxes and oils, paraffinic hydrocarbons; silicone oils; aliphatic and aromatic esters; higher alcohols and ethers; polyethylene and copolymers of polyethylene and mixtures thereof.
  • sucrose fatty acid polyesters for example sucrose octaisostearate, sucrose octa-2-ethylhexanoate, those derived from palm and palmkernal oil mixtures, soyabean oil, soyabean and palm oil mixtures, palm oil, coconut oil and mixed fish oils
  • high melting point triglycerides eg.
  • polyethylene homopolymers such as A-C polyethylene 1702 (trademark) , A-C polyethylene 617 (trademark) , A-C polyethylene 6 (trademark)
  • polyethylene vinyl acetate copolymers such as A-C ethylene-vinyl acetate 405 (trademark) , A-C ethylene vinyl acetate 400 (trademark)
  • gel compositions according to the invention comprise 1 to 40 wt % of the composition, even more preferably 10 to 30 wt % of the composition of the secondary thickener.
  • the gel composition according to the invention can optionally comprise other ingredients to provide additional skin or hair benefits.
  • Such ingredients include healing agents, humectants, thickeners, antioxidants, stabilisers, film formers, emulsifiers, surfactants, sunscreens, preservatives, perfumes and colourants.
  • the gel composition according to the invention can also comprise other ingredients conventionally used in cosmetic products which are suited to topical application to human skin or hair .
  • ingredients when present, can form up to 50% by weight of the composition and can conveniently form the balance of the gel base.
  • the invention also provides a process for the preparation of a gel suitable for topical application to skin or hair, which comprises the step of blending a layered, double hydroxide as herein defined, with a vegetable oil and a secondary thickener compound as herein defined.
  • the layered double hydroxide and vegetable oil are heated together with stirring to dissolve the layered double hydroxide.
  • the suspension is then subjected to high shearing forces until thickening has occurred.
  • Gel compositions according to the invention can be used for providing an occlusive layer on human skin, to reduce moisture loss, following topical application thereto of the gel composition.
  • the skin can thereby be protected from adverse climatic conditions, for example from excessive exposure to sun and wind, or from detergent damage, for example that following immersion of the hands in aqueous detergent solution when washing dishes or clothes.
  • a small quantity of the gel composition for example from 1 to 5g, is applied to the skin or hair from a suitable container or applicator and, if necessary, it is then spread over and/or rubbed into the skin or hair using the hand or fingers or a suitable spreading device.
  • the gel composition of the invention can be formulated as a soft solid or jelly-like product having the rheological and other physical properties as herein defined, and it can be packaged in a suitable container to suit its viscosity and intended use by the consumer.
  • the gel composition can be stored in a deformable tube or in a lidded jar.
  • the invention accordingly also provides a closed container containing the gel composition as herein defined.
  • Viscosity measurements were made using a Brookfield Viscometer: a multispeed rotational viscometer calibrated to measure the torque required to rotate a spindle, attached to a Beryllium copper spring, at constant speed. The measurements were taken using a Brookfield model RVT, at a speed of 20 r.p.m., using a T-bar spindle D (cross bar length 2.1cm), at room temperature (ca 23°C) and using a Helopath stand.
  • the T-bar spindle D was attached to the viscometer coupling and the instrument levelled using an internal spirit gauge.
  • VISCOSITY READING X SPINDLE FACTOR*
  • the gel composition according to the invention have a significant Occlusivity Value if secondary thickeners are included in the composition, such compositions may be employed like petrolatum, to provide an occlusive layer on skin or elsewhere on the body surface.
  • secondary thickeners such compositions may be employed like petrolatum, to provide an occlusive layer on skin or elsewhere on the body surface.
  • the gel composition will have an Occlusivity Value of at least 20%, as measured by the Occlusivity Value Test. Details of how this test is performed are given below.
  • a 5ml beaker for example a Dispo beaker available from American Scientific Products, the diameter of the open end ooff wwhhiicchh iiss 2255mmmm ((ii..e. an area of 5cm 2) , i.s used to provide an occlusivity cell,
  • lml distilled water is introduced into the beaker and a film of Visking dialysis tubing is stretched across the open end of the beaker and fixed in place with adhesive, for example Assembly Aid Adhesive (3M) .
  • adhesive for example Assembly Aid Adhesive (3M)
  • the rate of water loss through the Visking film at 20°C, at atmospheric pressure and at 50% external relative humidity, is determined by measuring the decrease in weight of the beaker with time using a Sartorius 4503 microbalance, with a D to A converter feeding the output to a chart recorder.
  • a product whose Occlusivity Value is to be tested i.e. the gel composition of the invention is applied as a film to the surface of the Visking dialysis tubing.
  • the test substance is liquid or a soft solid, it can be applied using a plastic-gloved finger.
  • the test material is a solid, it is necessary first to melt it as it is applied to the surface of the Visking dialysis film.
  • the new steady-state water loss rate under the same physical conditions of pressure, temperature and relative humidity, is then recorded after excess water from the product has been lost.
  • Occlusivity of the product film ie. the gel composition
  • Occlusivity is normally determined 4 times for each sample.
  • the sample loading is determined from the increase in recorded weight immediately after application to the Visking film of the composition of the invention. Since the loading is not reproducible precisely, a straight line is fitted to a loading versus occlusivity plot (by linear regression) and the occlusivity at a typical consumer product loading of lOg/sq m is then interpolated. In each case, the occlusivity is approximately linearly dependent on the loading for the range covered.
  • the occlusivity is then expressed as an arithmetic mean of the 4 determinations + 2 standard errors for 95% significance.
  • the layered double hydroxide powder was suspended in rapeseed oil and heated on a hot-plate to 90°C with stirring.
  • a shearing aid, polyoxyethylene-(4)-lauryl alcohol (0.05% based on the powder used) was then added and the suspension was heated to about 120°C with stirring until starting to foam slightly. Without cooling further the suspension was then subjected to high shearing forces in a Silverson mixer for about 1-5 minutes until thickening has occurred.
  • secondary structurants are used (examples 1-2) , these are added to the oil and heated, with stirring, until molten before addition of the layered double hydroxide.
  • the polyethylene/vinyl acetate co-polymer was added with the hydrotalcite and the mixture was stirred through the cloud point ( ⁇ 85°C) of the polyethylene/vinyl acetate co-polymer when cooling to ensure efficient gelling.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Chemical & Material Sciences (AREA)
  • Emergency Medicine (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dispersion Chemistry (AREA)
  • Insects & Arthropods (AREA)
  • Zoology (AREA)
  • Dermatology (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)

Abstract

Composition occlusive sous forme de gel renfermant: (i) un hydroxyde double en couches présentant la structure générale suivante [A(1-x)Alx(OH)2]?x By-¿x/y . ZH2O dans laquelle A correspond à des ions zinc, magnésium ou calcium, B représente un anion à couche intermédiaire, Y représente une charge sur l'anion, x est compris entre 0,1 et 0,5, x est compris entre 0 et 100, à condition que au moins 50 % de l'anion de couche intermédiaire soit choisi parmi un acide monocarboxylique, un sulfate de monoalkyle, un sulfate d'éther de monoalkyle, un sulfonate de benzène d'alkyle et des mélanges de ces substances; (ii) une huile végétale liquide à température ambiante et (iii) un épaississant secondaire solide à température ambiante.
PCT/EP1993/003097 1992-11-11 1993-11-04 Composition cosmetique WO1994010973A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU54207/94A AU5420794A (en) 1992-11-11 1993-11-04 Cosmetic composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB929223603A GB9223603D0 (en) 1992-11-11 1992-11-11 Cosmetic composition
GB9223603.3 1992-11-11

Publications (1)

Publication Number Publication Date
WO1994010973A1 true WO1994010973A1 (fr) 1994-05-26

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ID=10724887

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1993/003097 WO1994010973A1 (fr) 1992-11-11 1993-11-04 Composition cosmetique

Country Status (3)

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AU (1) AU5420794A (fr)
GB (1) GB9223603D0 (fr)
WO (1) WO1994010973A1 (fr)

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WO1996016634A1 (fr) * 1994-12-02 1996-06-06 Unilever Plc Composition de cosmetique
FR2729851A1 (fr) * 1995-01-27 1996-08-02 Fiabila Composition de produit cosmetique pour ongles et dispositif d'application correspondant
WO2002010105A1 (fr) * 2000-07-27 2002-02-07 Jemco Inc. Methode de traitement de compose fluore et substance traitee
WO2002017864A1 (fr) * 2000-08-31 2002-03-07 The Procter And Gamble Company Composition revitalisante capillaire a appliquer avant le shampooing
WO2003066016A1 (fr) * 2002-02-08 2003-08-14 The Procter & Gamble Company Compositions de rinçage de soins cutanes
US6673755B2 (en) 2002-01-16 2004-01-06 The Procter & Gamble Company Personal cleansing compositions containing cleansing and skin active phases separated by one or more packaging barriers
WO2004082647A1 (fr) * 2003-03-18 2004-09-30 The Procter & Gamble Company Composition a base d'un materiau en couches contenant du zinc presentant une labilite de zinc relative elevee
US7026308B1 (en) 1999-06-25 2006-04-11 The Procter & Gamble Company Topical anti-microbial compositions
US7511003B2 (en) 2002-11-04 2009-03-31 The Procter & Gamble Company Striped liquid personal cleansing compositions containing a cleansing phase and a separate benefit phase with improved stability
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US8147853B2 (en) 2005-02-15 2012-04-03 The Procter & Gamble Company Personal care compositions containing hydrophobically modified non-platelet particles
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US8314054B2 (en) 2004-02-27 2012-11-20 The Procter & Gamble Company Mild multi-phased personal care composition
US8796252B2 (en) 1999-06-25 2014-08-05 Arch Chemicals, Inc. Pyrithione biocides enhanced by zinc metal ions and organic amines
US8951947B2 (en) 2003-12-24 2015-02-10 The Procter & Gamble Company Multi-phase personal cleansing compositions comprising a lathering cleansing phase and a non-lathering structured aqueous phase
US9114087B2 (en) 2003-05-01 2015-08-25 The Procter & Gamble Company Process for making visually distinctive multiple liquid phase compositions
US9381148B2 (en) 2003-03-18 2016-07-05 The Procter & Gamble Company Composition comprising particulate zinc material with a high relative zinc lability
US9381382B2 (en) 2002-06-04 2016-07-05 The Procter & Gamble Company Composition comprising a particulate zinc material, a pyrithione or a polyvalent metal salt of a pyrithione and a gel network
JP2016190854A (ja) * 2013-05-13 2016-11-10 テイカ株式会社 オレイン酸を選択的に吸着する層状複水酸化物およびこの層状複水酸化物を用いた化粧料
US9636283B2 (en) 2005-12-15 2017-05-02 The Procter & Gamble Company Non-migrating colorants in multi-phase personal cleansing compositions
US9675530B2 (en) 2002-09-20 2017-06-13 The Procter & Gamble Company Striped liquid personal cleansing compositions containing a cleansing phase and a seperate benefit phase
WO2017103787A1 (fr) * 2015-12-15 2017-06-22 Universidad De Guadalajara Nanoparticules d'hydroxydes doubles lamellaires qui contiennent des composés non polaires d'origine végétale, procédé de séparation et de libération sélective de ces composés
US10945935B2 (en) 2016-06-27 2021-03-16 The Procter And Gamble Company Shampoo composition containing a gel network
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US11419805B2 (en) 2017-10-20 2022-08-23 The Procter & Gamble Company Aerosol foam skin cleanser
US11497691B2 (en) 2018-12-14 2022-11-15 The Procter & Gamble Company Shampoo composition comprising sheet-like microcapsules
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US11633072B2 (en) 2021-02-12 2023-04-25 The Procter & Gamble Company Multi-phase shampoo composition with an aesthetic design
US11896689B2 (en) 2019-06-28 2024-02-13 The Procter & Gamble Company Method of making a clear personal care comprising microcapsules
US11932448B2 (en) 2020-02-14 2024-03-19 The Procter & Gamble Company Bottle adapted for storing a liquid composition with an aesthetic design suspended therein
US12053130B2 (en) 2021-02-12 2024-08-06 The Procter & Gamble Company Container containing a shampoo composition with an aesthetic design formed by bubbles
US12268765B2 (en) 2016-10-10 2025-04-08 The Procter & Gamble Company Personal care compositions substantially free of sulfated surfactants and containing a gel network

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EP0419759A2 (fr) * 1989-09-28 1991-04-03 Giulini Chemie GmbH Dérivés d'hydroxyacides gras comprenant de l'aluminium, du magnésium et des lipogels thermostabiles préparés avec ceux-ci

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AU5420794A (en) 1994-06-08

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