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WO2016096626A1 - Composition de support pour actifs volatils - Google Patents

Composition de support pour actifs volatils Download PDF

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Publication number
WO2016096626A1
WO2016096626A1 PCT/EP2015/079337 EP2015079337W WO2016096626A1 WO 2016096626 A1 WO2016096626 A1 WO 2016096626A1 EP 2015079337 W EP2015079337 W EP 2015079337W WO 2016096626 A1 WO2016096626 A1 WO 2016096626A1
Authority
WO
WIPO (PCT)
Prior art keywords
range
carrier composition
volatile oil
volatile
composition
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/EP2015/079337
Other languages
English (en)
Inventor
Somnath Das
Kingshuk Dutta
Shreya Mukherjee
Amitava Pramanik
Priyanka SARKAR
Shanthi APPAVOO
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Unilever NV
Conopco Inc
Original Assignee
Unilever NV
Conopco Inc
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 NV, Conopco Inc filed Critical Unilever NV
Publication of WO2016096626A1 publication Critical patent/WO2016096626A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/26—Aluminium; Compounds 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/27—Zinc; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • 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
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • C11D3/505—Protected perfumes encapsulated or adsorbed on a carrier, e.g. zeolite or clay
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/56—Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms

Definitions

  • a carrier composition for volatile actives is
  • the present invention relates to a carrier composition for volatile actives.
  • the carrier composition is useful for stabilisation and slow release of the volatile actives in personal care, hygiene or laundry compositions.
  • Volatile oils are generally volatile substances and volatile oils are used in various consumer products like soaps and detergents and other personal care and hygiene compositions. When the volatile actives such as volatile oils are added in these compositions, there is an interaction between the detergent actives and the volatile actives thereby reducing their effectiveness for e.g., the aesthetic effects of the volatile oil.
  • Stabilization of volatile organic actives such as volatile oil and essential oils in consumer compositions is a challenge. Moreover, even if such actives are stabilized in the compositions, their effective deposition onto substrates is often hindered. For example in fabric cleaning and fabric care compositions contain high concentration of surfactants, polymers and other adjuncts, whereby volatile organic actives tend to get entrapped in the micelles/ macromolecular aggregates thereby lowering its partitioning onto fabric substrates.
  • Various techniques, such as encapsulation of the volatile oils have been employed to hinder or delay the release of the volatile oil from the composition so that the composition remains aesthetically pleasing for a prolonged length of time. However, this is expensive and requires further functionalization of the polymeric encapsulates to facilitate efficient deposition. Once deposited, the polymer encapsulates requires an external stimuli such as mechanical shear/ heat etc. for releasing the volatile organic active.
  • Insoluble inorganic materials would be particularly preferred, owing to their ability to act as structurants in the composition.
  • hydrophobic inorganic materials would be preferred owing to enhanced stability arising from hydrophobic interactions with the hydrophobic volatile organic actives.
  • US2010/0313786 (EVERSDIJK JACOBUS et.al, 2010), discloses an inorganic material with a plate like structure wherein the inorganic material is intercalated with a biocide. It discloses the use of ionic organic modifiers to prepare hydrophobic layered double hydroxides. It does not disclose the use of such hydrophobic layered double
  • hydroxides for sustained volatile oil delivery or for use in compositions with high concentration of surfactants.
  • JP6048742 discloses a micellar anionic organic surfactant and a non charged organic substance intercalated in the layers of a layered double hydroxide for sustained release of volatile oils or chemicals with medicinal properties.
  • the layered double hydroxide is impregnated with CO3 2" , water and preferably non-chargeable organic compounds, thermally decomposed to form oxide solid solution and hydrated at the presence of organic anionic surfactant micelle such as sodium laurate, sodium dodecyl sulphonate and sodium n-dodecyl benzene sulphonate to form intercalation compound containing composite hydroxides, anionic micelle and preferably non-chargeable compound.
  • WO2009/080597 discloses a process and the use of fatty acids as one of the intercalating agents, which can be added during the process of formation of hydrophobic layered double hydroxides.
  • WO12101222 discloses a deodorant composition comprising a layered double hydroxide and an essential oil but does not have an alkyl anion which makes the layered double hydroxide hydrophobic and thus benefits of sustained release of the essential oil will be poor.
  • the present inventors have found that the volatile organic actives can be entrapped in a hydrophobic layered double hydroxide for use in compositions to achieve deposition of volatile actives onto the substrates to ensure slow release of actives without any external stimuli.
  • the present inventors by selecting a particular ratio between the interlayer anion which is attached to an alkyl group to the volatile oil having a evaporation coefficient in the range from 1 to 60 have been able to provide improved sustained release of the volatile oil when used in personal care, hygiene or laundry compositions which has high concentration of surfactants. It is an object of the present invention to enable slow release of volatile actives without any external stimuli.
  • a carrier composition for volatile actives comprising:
  • M" is a divalent cation selected from calcium, magnesium or zinc
  • M'" is a trivalent cation selected from aluminum or iron
  • a n - is an interlayer anion selected from carboxylate, hydroxide, halide, nitrate, sulphate, carbonate, phosphate, sulphonate or their mixtures having at least one anion attached to an alkyl group having carbon chain length of 8 to 18, and x has a value in the range from 0.1 to 0.5, n has a value in the range from
  • m has a value in the range from 1 to 10 and
  • the layered double hydroxides have either flat or cone shaped structure and it is preferred to have them in the cone shaped structure.
  • the carrier composition comprises:
  • a process for entrapment of volatile oil in the carrier composition as claimed in any of the preceding claims comprising mixing hydrophobic layered double hydroxide with volatile oil and subjecting the mixture to evaporation under vacuum in the range from 40x10 3 to 80x10 3 Pascal pressure.
  • a personal care or hygiene composition comprising:
  • a carrier composition for volatile actives comprising:
  • M" is a divalent cation selected from calcium, magnesium or zinc
  • M'" is a trivalent cation selected from aluminum or iron
  • a n - is an interlayer anion selected from carboxylate, hydroxide, halide, nitrate, sulphate, carbonate, phosphate, sulphonate or their mixtures having at least one anion attached to an alkyl group having carbon chain length of 8 to 18, and x has a value in the range from 0.1 to 0.5, n has a value in the range from 1 to 4, m has a value in the range from 1 to 10 and
  • the ratio of the interlayer anion to the volatile oil is preferably in the range from 15: 1 to 5: 1
  • the layered double hydroxides have either flat or cone shaped structure and it is preferred to have them in the cone shaped structure.
  • the layered double hydroxide has the formula: ⁇ " ⁇ - ⁇ '" ⁇ (OH) 2 (A n -Vn.mH 2 0
  • M" is a divalent cation selected from calcium, magnesium or zinc and more preferably calcium; M'" is a trivalent cation selected from aluminum or iron and more preferably aluminium;
  • a n - is an interlayer anion selected from carboxylate, hydroxide, halide, nitrate, sulphate, carbonate, phosphate, sulphonate or their mixtures having at least one anion attached to an alkyl group having carbon chain length of 8 to 18. It is preferable that the interlayer anion is selected from sulphate or sulphonate having at least one anion attached to an alkyl group having carbon chain length of 8 to 18.
  • x has a value in the range from 0.1 to 0.5 and preferably 0.25 to 0.4 and more preferably 0.33.
  • "n" has a value in the range from 1 to 4 and preferably 1 to 2 and m has a value in the range from 1 to 10 and preferably 2 to 6 and more preferably 4.
  • the anion is preferably alkyl sulphate or sulphonate and the carbon chain length of the alkyl group is 8 to 18 and preferably 8 to 16.
  • Contact angle is a measure of hydrophobicity and it is preferred that the contact angle of the layered double hydroxide is 100 to 175 degrees and more preferably 120 to 150 degrees.
  • the volatile oil is selected from one having an evaporation coefficient in the range from 1 to 60 and preferably from 1 to 20.
  • the volatile oil is preferably a perfume or antimicrobial material.
  • the volatile oil may preferably be synthetically prepared or naturally occurring hydrocarbons.
  • the volatile oil is preferably selected from alcohols, aldehydes, ketones, esters, phenols, carboxylic acids and more preferably be selected from opinene, camphene, ⁇ -pinene, myrcene, limonene, cis-ocimene, camphor, linalool, methyl chavicol, ⁇ -terpineol, citronellol, geraniol, methyl cinnamate, citral, phenethyl alcohol, eugenol acetate, cinnamic aldehyde, benzyl benzoate and eugenol.
  • the volatile oil may preferably be a single compound or a mixture any of these.
  • the volatile oil for incorporation in the carrier composition is preferably dispersed in a low boiling solvent which is preferably selected from methanol, ethanol, iso-propanol or acetone in a ratio preferably in the range from 1 :20 to 1 :60 and the mixture is preferably mixed at room temperature which is about 25 to 30 °C.
  • the evaporation coefficient is according to the Poucher's Scale.
  • the scale has been explained in the book "Poucher's Perfumes, Cosmetics and Soaps; Vol 2, Ninth Edition, Author: W A Poucher; ISBN: 0412273500". Also described therein is the method of determination of evaporation coefficient, which in turn determines the type of note of odour classification and fixation.
  • the carrier composition comprises:
  • the carrier composition comprises 90 to 96 wt% hydrophobic layered double hydroxide and 4 to 10 wt% volatile oil.
  • a process for entrapment of volatile oil in the carrier composition comprising mixing hydrophobic layered double hydroxide with volatile oil and subjecting the mixture to evaporation under a vacuum in the range from 40x10 3 to 80x10 3 Pascal pressure.
  • the volatile oil having a evaporation coefficient in the range from 1 to 60 is dispersed in preferably a low boiling solvent such as methanol, ethanol, iso-propanol or acetone in a ratio preferably in the range from 1 :20 to 1 :60 and the mixture is preferably mixed at room temperature which is about 25 to 30°C. The mixture was added to the
  • hydrophobic layered double hydroxide particles according to the invention under constant mixing without allowing them to form dough.
  • the mixture preferably was then subjected to vacuum in the range from 40x10 3 to 80x10 3 Pascal pressure to preferably remove excess volatile oil and the solvent that it was dispersed in.
  • the dried particles were preferably stored in airtight containers.
  • a personal care or hygiene composition comprising:
  • the detergent active used in the process may be soap or non-soap surfactants and is present in an amount of 3 to 40%, preferably 5 to 20% by weight of the composition.
  • the detergent active is preferably an anionic surfactant.
  • the detergent active may be generated by neutralising the acid precursor of the active with an alkali or preformed active may be used.
  • the detergent active is mixed with water and/or other solvents and heated to form a melt. It is preferred that the anionic surfactant is a soap.
  • the term total fatty matter, usually abbreviated to TFM is used to denote the percentage by weight of fatty acid and triglyceride residues present in soaps without taking into account the accompanying cations.
  • an accompanying sodium or potassium cation will generally amount to about 8% by weight.
  • soap denotes salts of carboxylic fatty acids.
  • the soap may be derived from any of the triglycerides conventionally used in soap manufacture - consequently the carboxylate anions in the soap may contain from 8 to 16 carbon atoms.
  • the soap may be obtained by saponifying a fat and/or a fatty acid.
  • the fats or oils generally used in soap manufacture may be such as tallow, tallow stearines, palm oil, palm stearines, soya bean oil, fish oil, castor oil, rice bran oil, sunflower oil, coconut oil, babassu oil, palm kernel oil, and others.
  • the fatty acids are derived from oils/fats selected from coconut, rice bran, groundnut, tallow, palm, palm kernel, cottonseed, soybean, castor etc.
  • the fatty acid soaps can also be synthetically prepared (e.g. by the oxidation of petroleum or by the hydrogenation of carbon monoxide by the Fischer-Tropsch process). Resin acids, such as those present in tall oil, may be used. Naphthenic acids are also suitable.
  • a typical fatty acid blend consists of 5 to 30% coconut fatty acids and 70 to 95% fatty acids ex hardened rice bran oil.
  • Fatty acids derived from other suitable oils/fats such as groundnut, soybean, tallow, palm, palm kernel, etc., may also be used in other desired proportions.
  • Non-Soap detergents are non-Soap detergents:
  • composition according to the invention will preferably comprise detergent actives generally chosen from anionic, nonionic, cationic, zwitterionic detergent actives or mixtures thereof.
  • detergent-active compounds are compounds commonly used as surface-active agents given in the well-known textbooks "Surface Active Agents", Volume I by Schwartz and Perry and “Surface Active Agents and Detergents", Volume II by Schwartz, Perry and Berch or "Handbook of Surfactants", M.R. Porter, Blackie Publishers, 1991 .
  • the conventional ingredients used in detergent compositions may suitably be incorporated in the composition.
  • Some of the ingredients, which may be included in the composition prepared by the process of the invention include builders, inorganic particulates, fillers, benefit agents and other minor additives.
  • the benefit agents, which may be included, are moisturisers and humectants. Examples of these are Carbopol® 934, ethoxylated castor oil, paraffin oils, lanolin and its derivatives. Silicone compounds such as silicone surfactants like DC3225C (Dow Corning) and/or silicone emollients, silicone oil (DC-200 Ex-Dow Corning) may also be included.
  • Sunscreens such as 4- tertiary butyl-4'-methoxy dibenzoylmethane (available under the trade name PARSOL 1789 from Givaudan) and/or 2-ethyl hexyl methoxy cinnamate (available under the trade name PARSOL® MCX from Givaudan) or other UV-A and UV-B sunscreens may be used.
  • Water soluble glycols such as propylene glycol, ethylene glycol, glycerol, may be employed at levels upto 10%.
  • minor additives examples include enzymes, antiredeposition agents, fluorescers, colour, preservatives, perfumes, bleaches, bleach precursors, bleach stabilisers, sequestrants, soil release agents (usually polymers) and other polymers may optionally be incorporated up to 10 wt%.
  • the carrier composition may preferably be included in any personal or hygiene composition that may or may not have a detergent active.
  • Product format may preferably be solid, powder, paste or liquid composition.
  • the compositions may be personal cleaning bars or liquids, fabric cleaning compositions, hard surface cleaning compositions or talcum powders. It is particularly preferred to include the carrier composition in a fabric conditioner liquid composition.
  • CaAI-LDH was intercalated with dodecyl sulphate (DS) anion by a hydrothermal method where 5.71 g (0.01 mole) CDS powder was taken in a 250 mL hydrothermal bottle containing 80 mL of distilled water. The mixture was heated at 85°C for 2 h and 1 .88 g (0.005 mole) AI(N0 3 )3.9H 2 0 dissolved in 20 mL water was added to the solution at 85°C.
  • Hydrophilic plate shaped Ca-AI LDH was prepared by adding drop wise 200 mL of aqueous solution containing 47.2 g of Ca(NOs)2.4H2O(0.2 moles) and 38.5 g of AI(N0 3 )3.9H 2 0 (0.1 mole) to 1 L of water alongwith dropwise addition of 200 mL 3.2 M NaOH solution at a rate of 2.5mL/min at 70 ° C followed by ageing at 80 ° C with stirring for 4.5 hours. The pH of the resultant mixture was maintained at 12 using NaOH. The precipitate formed was filtered and washed thoroughly with hot water. The precipitate was air dried for 16 hours and then dried at 70 ° C for 8 hours. d.
  • Hydrophilic plate shaped Mg-AI LDH was prepared by heating 50 mL of distilled water to 65 °C to which 100 mL of an aqueous mixture of 3 mol Mg(NOs)2-6H20 and 1 mol ⁇ ( ⁇ 3)3-9 ⁇ 2 ⁇ was added over a period of 1 hour along with 100 mL of an aqueous solution of 0.2 mol (NH 4 )2CC>3
  • the pH of the mixture was continuously monitored by pH meter and maintained at pH 8 by using NH 4 OH (as 35% aqueous ammonia solution).
  • the resulting mixture stirred vigorously 65 °C for 3 hours and then filtered and washed with distilled water until the filtrate was as near pH 7.
  • the extracts were pooled and transferred to a GC vial and sealed immediately. All the vials were incubated at 40 ° C for 10 minutes and the concentration of these actives were analyzed using GC by direct injection technique. The following GC conditions were used for the study:
  • Capillary column CPWAX 52CB (30 m length x 0.25mm Internal Diameter)
  • Carrier gas Helium (1 mL/minute)
  • Thermostat condition Temperature 40 °C; Incubation time 10 minutes
  • compositions were kept exposed to air and samples were analysed by GC after 0, 48, 72 and 120 hours.
  • the data is presented in Table 3.
  • compositions were exposed to air and samples were analysed by GC after elapse of 0, 72, 96 and 240 hours.
  • perfume ratio of 5:1 to 13:1 acts as superior perfume delivery agent for limonene, which is a highly volatile material and stabilisation of limonene is significantly beneficial.
  • perfume delivery benefits were observed for limonene, however there was a significant difference for linalool. Delivery of citral was superior when the ratio was between 5:1 and 25:1.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Inorganic Chemistry (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Dispersion Chemistry (AREA)
  • Dermatology (AREA)
  • Fats And Perfumes (AREA)
  • Lubricants (AREA)

Abstract

La présente invention concerne une composition de support pour des actifs volatils. En particulier, la composition de support est utile pour la stabilisation et la libération lente d'actifs volatils dans des compositions de lessive, d'hygiène ou de soins personnels. La composition de support pour des actifs volatils comporte un hydroxyde à double couche hydrophobe de formule : M"1-XM'"X (OH)2 (An-)x/n.mH2O, où M" est un cation divalent choisi parmi le calcium, le magnésium ou le zinc, M'" est un cation trivalent choisi parmi l'aluminium ou le fer, An- est un anion de couche intermédiaire choisi parmi un carboxylate, un hydroxyde, un halogénure, un nitrate, un sulfate, un carbonate, un phosphate, un sulfonate ou leurs mélanges ayant au moins un anion fixé à un groupe alkyle ayant une longueur de chaîne carbonée de 8 à 18, et x possède une valeur dans la plage de 0,1 à 0,5, n possède une valeur dans la plage de 1 à 4, m possède une valeur dans la plage de 1 à 10, et une huile volatile ayant un coefficient d'évaporation dans la plage de 1 à 60, le rapport d'anion de couche intermédiaire à l'huile volatile étant dans la plage de 25:1 à 4:1 en poids.
PCT/EP2015/079337 2014-12-17 2015-12-11 Composition de support pour actifs volatils Ceased WO2016096626A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP14198405.4 2014-12-17
EP14198405 2014-12-17

Publications (1)

Publication Number Publication Date
WO2016096626A1 true WO2016096626A1 (fr) 2016-06-23

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PCT/EP2015/079337 Ceased WO2016096626A1 (fr) 2014-12-17 2015-12-11 Composition de support pour actifs volatils

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AR (1) AR103053A1 (fr)
WO (1) WO2016096626A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108993377A (zh) * 2018-08-13 2018-12-14 武汉理工大学 超薄锌铝类水滑石纳米片及其制备方法和应用
US11242460B2 (en) 2016-11-15 2022-02-08 Scg Chemicals Co., Ltd. Surface modified layered double hydroxide

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0648742A (ja) * 1992-07-27 1994-02-22 Nitto Chem Ind Co Ltd 層間化合物
WO1994010972A1 (fr) * 1992-11-11 1994-05-26 Unilever Plc Composition cosmetique
WO1994014409A1 (fr) * 1992-12-22 1994-07-07 Unilever Plc Compositions deodorantes
WO2009080597A2 (fr) * 2007-12-19 2009-07-02 Akzo Nobel N.V. Procédé pour préparer un hydroxyde double lamellaire organiquement modifié
WO2012081135A1 (fr) * 2010-12-17 2012-06-21 L'oreal Composition cosmétique
WO2012101222A1 (fr) * 2011-01-28 2012-08-02 Ilios Srl Composition déodorante
WO2014185201A1 (fr) * 2013-05-13 2014-11-20 テイカ株式会社 Hydroxyde double en couches capable d'absorber sélectivement les acides gras insaturés et cosmétique produit en utilisant ledit hydroxyde double en couches

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0648742A (ja) * 1992-07-27 1994-02-22 Nitto Chem Ind Co Ltd 層間化合物
WO1994010972A1 (fr) * 1992-11-11 1994-05-26 Unilever Plc Composition cosmetique
WO1994014409A1 (fr) * 1992-12-22 1994-07-07 Unilever Plc Compositions deodorantes
WO2009080597A2 (fr) * 2007-12-19 2009-07-02 Akzo Nobel N.V. Procédé pour préparer un hydroxyde double lamellaire organiquement modifié
WO2012081135A1 (fr) * 2010-12-17 2012-06-21 L'oreal Composition cosmétique
WO2012101222A1 (fr) * 2011-01-28 2012-08-02 Ilios Srl Composition déodorante
WO2014185201A1 (fr) * 2013-05-13 2014-11-20 テイカ株式会社 Hydroxyde double en couches capable d'absorber sélectivement les acides gras insaturés et cosmétique produit en utilisant ledit hydroxyde double en couches

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
KINGSHUK DUTTA ET AL: "Synthesis of a novel cone-shaped CaAl-layered double hydroxide (LDH): its potential use as a reversible oil sorbent", CHEMICAL COMMUNICATIONS, vol. 49, no. 57, 1 July 2013 (2013-07-01), pages 6427 - 9, XP055190593, ISSN: 1359-7345, DOI: 10.1039/c3cc42260g *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11242460B2 (en) 2016-11-15 2022-02-08 Scg Chemicals Co., Ltd. Surface modified layered double hydroxide
CN108993377A (zh) * 2018-08-13 2018-12-14 武汉理工大学 超薄锌铝类水滑石纳米片及其制备方法和应用

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