WO2019110290A1 - Composition anti-transpirante comprenant du zirconium - Google Patents

Composition anti-transpirante comprenant du zirconium Download PDF

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Publication number
WO2019110290A1
WO2019110290A1 PCT/EP2018/081869 EP2018081869W WO2019110290A1 WO 2019110290 A1 WO2019110290 A1 WO 2019110290A1 EP 2018081869 W EP2018081869 W EP 2018081869W WO 2019110290 A1 WO2019110290 A1 WO 2019110290A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
zirconium
compositions
antiperspirant
skin
Prior art date
Application number
PCT/EP2018/081869
Other languages
English (en)
Inventor
Xiaoke Li
Renjiang LIU
Philip Christopher Waterfield
Huanjun ZHOU
Original Assignee
Unilever N.V.
Unilever Plc
Conopco, Inc., D/B/A Unilever
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 N.V., Unilever Plc, Conopco, Inc., D/B/A Unilever filed Critical Unilever N.V.
Publication of WO2019110290A1 publication Critical patent/WO2019110290A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • 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
    • A61K8/0216—Solid or semisolid forms
    • A61K8/0229—Sticks
    • 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
    • A61K8/046—Aerosols; Foams
    • 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
    • A61K8/28—Zirconium; 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
    • A61K8/30—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
    • A61K8/41—Amines
    • 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
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30—Characterized by the absence of a particular group of ingredients
    • A61K2800/31—Anhydrous
    • 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
    • A61K2800/58—Metal complex; Coordination compounds

Definitions

  • the present invention is in the field of antiperspirant compositions.
  • the present invention more particularly relates to compositions comprising a zirconium based antiperspirant active which is effective in ensuring anti-perspirant benefits.
  • the present invention relates to compositions, such as those that contain antiperspirant actives. These actives are added to compositions to reduce perspiration on application to the surface of the body, particularly to the underarm regions of the human body viz. the axilia.
  • Antiperspirant actives are typically astringent metal salts such as those of aluminium or zirconium. However conventional aluminium or zirconium salts have certain disadvantages. In particular, it may cause local skin irritation.
  • Antiperspirant actives are usually incorporated in compositions at low pH, in the range of 2 to 7.
  • US4650671A (Claus Riemann 4 Co. ApS, 1984) discloses a method for controlling perspiration, and kit for carrying out that method.
  • the method involves the separate, sequential application of an AICI3- or ZrCI4- containing antiperspirant composition and a physiologically tolerable basic buffer-containing composition. Separate, successive application of the antiperspirant and the buffer prevents skin irritation or damage to the user's clothes attributable to acid formed from the antiperspirant, and provides antiperspirant activity.
  • US3407254 (Bernard Siegal et al, 1968) discloses an antiperspirant composition comprising an aqueous carrier and a zirconium complex having specific structure.
  • the composition has a pH in the range of about 0.5 to 3.5.
  • the present inventors have tested the zirconium salts proposed in the past for anti- perspirancy benefits and discovered that they suffer either from being unstable when formulated or cause local skin irritation because of the hydrolysis of zirconium salts. It is desired that the antiperspirant active does not degrade when formulated and stored for periods of time (sometimes up to several months) before they are used by the consumer. When the formulated product is applied to the skin it is desired that the antiperspirant active can deliver antiperspirant benefit by forming particles with the biomolecules in the sweat pores such that it can clog or gel in the sweat pores and inhibit further sweating. The present inventors then found out that this problem can be solved by formulating a specific zirconium complex in a cosmetically acceptable carrier.
  • an antiperspirant composition comprising
  • zirconium complex is tetrakis[[2,2’,2”-nitri!otris[ethanolato]](1-)- M.Ojzirconium (CAS number: 101033-44-7) having the following structure:
  • therapeutic method of reducing perspiration comprising the step of applying a composition as claimed in the first aspect on to the desired skin surface.
  • compositions of the invention are typically “personal care compositions”, suitable for cosmetic use as detailed below. Further, use of the compositions of the invention is typically cosmetic, non-therapeutic use.
  • the compositions may be used for the therapeutic treatment of hyperhidrosis (extreme sweating).
  • the compositions of the invention are used for therapeutic treatment.
  • the compositions are used for non-therapeutic applications, more particularly for cosmetic purposes.
  • composition is meant to include a composition for topical application to the skin of mammals, especially humans.
  • a composition is preferably of the leave-on type.
  • a leave-on composition is meant a composition that is applied to the desired skin surface and left on for a period of time (say from one minute to 24 hours) after which it may be wiped or rinsed off with water, usually during the regular course of personal washing.
  • the composition may also be formulated into a product which is applied to a human body for improving the appearance, cleansing, odor control or general aesthetics.
  • composition of the present invention can be in the form of a liquid, lotion, cream, foam, scrub, gel or stick form and may be delivered through a roll-on device or using a propellant containing aerosol can. It is especially useful for delivering low pH compositions to the axilla of an individual for anti- perspirancy benefits.
  • skin as used herein is meant to include skin on any part of the body (e.g., neck, chest, back, arms, underarms, hands legs, buttocks and scalp) especially the underarms.
  • the present invention is directed to delivering a zirconium based antiperspirant active on to the topical surface of a human body.
  • the active for inclusion in the composition is a zirconium complex where the zirconium is chelated by alkanolamine.
  • the zirconium complex in accordance with this invention is tetrakis[[2,2’,2”- nitrilotris[ethanolato]](1-)-N,0]zirconium (CAS number: 101033-44-7) having the following structure:
  • Tetrakis[[2,2 ⁇ 2”-nitrilotris[ethanolato]](1-)-N,0]zirconium (having CAS number: 101033- 44-7) is the zirconium aikanolamine chelated complex, as per this invention
  • the above zirconium alkanolamine complex is preferably included in 0.5 to 30%, more preferably 1 to 15%, furthermore preferably 3 to 10% by weight of the composition
  • Antiperspirant compositions of the present invention may advantageously comprise an additional antiperspirant active. Whilst this might be a conventional antiperspirant salt comprising Al and/or Zr, such as aluminium chlorohydrate or aluminium-zirconium chlorohydrate optionally complexed with glycine, it is preferred that any additional antiperspirant active is not of this type.
  • compositions of the present invention may also be incorporated in the compositions of the present invention.
  • Such components include skin care agents such emollients, humectants and skin barrier promoters; skin appearance modifiers such as skin lightening agents and skin smoothing agents; anti- microbial agents, in particular organic anti-microbial agents, and preservatives.
  • the anti-perspirant active can be applied cosmetically and topically to the skin, broadly speaking, by one of two methods. Different consumers prefer one method or the other. In one method, sometimes called a contact method, a composition is wiped across the surface of the skin, depositing a fraction of the composition as it passes. In the second method, sometimes called the non-contact method, the composition is sprayed from a dispenser held proximate to the skin, often in an area of about 10 to 20 cm 2 .
  • the spray can be developed by mechanical means of generating pressure on the contents of the dispenser, such as a pump or a squeezable sidewall or by internally generated pressure arising from a fraction of a liquefied propellant volatilising, the dispenser commonly being called an aerosol.
  • the carrier fluid comprises a solvent for the antiperspirant and in a second variation, the antiperspirant remains a particulate solid that is suspended in an oil, usually a blend of oils.
  • Stick or soft solid compositions are broadly speaking two classes of contact compositions, one of which is liquid and usually applied using a roll-on dispenser or possibly absorbed into or onto a wipe, and in the second of which the antiperspirant active is distributed within a carrier liquid that forms a continuous phase that has been gelled.
  • the carrier fluid comprises a solvent for the antiperspirant and in a second variation, the antiperspirant remains a particulate solid that is suspended in an oil, usually a blend of oils.
  • Stick or soft solid compositions are broadly speaking two classes of contact compositions, one of which is liquid and usually applied using a roll-on dispenser or possibly absorbed into or onto a wipe, and in the second of which the antiperspirant active is distributed within a carrier liquid that forms a continuous phase that has been gelled.
  • the carrier fluid comprises a solvent for
  • gellant for a continuous oil phase
  • materials including waxes, small molecule gelling agents and polymers. They each have their advantages and of them, one of the most popular class of gellant has comprised waxes, partly at least due to their ready availability and ease of processing, including in particular linear fatty alcohol wax gellants,
  • a gelled antiperspirant composition is applied topically to skin by wiping it across and in contact with the skin, thereby depositing on the skin a thin film.
  • ameliorating materials for example, di or polyhydric humectants and/or a triglyceride oil.
  • Liquid compositions that are applicable from a roll-on broadly speaking can be divided into two classes, namely those in which an antiperspirant active is suspended in a hydrophobic carrier, such as a volatile silicone and those in which the antiperspirant active is dissolved in a carrier liquid.
  • a hydrophobic carrier such as a volatile silicone
  • the antiperspirant active is dissolved in a carrier liquid.
  • the latter has proven to be more popular.
  • dissolving carrier liquid namely carriers that are predominantly alcoholic, which is to say the greater part of the dissolving carrier fluid comprises ethanol and the second class in which the carrier liquid is mainly water.
  • the former was very popular because ethanol is a mild bactericide in its own right, but its popularity waned because it stings, especially if the surface onto which the composition has been applied has been damaged or cut, such as can easily arise during shaving or other de-hairing operations.
  • the second class of formulations that is an alternative to alcoholic formulations comprise a dispersion of water-insoluble or very poorly water soluble ingredients in an aqueous solution of the antiperspirant.
  • emulsions Such compositions will be called emulsions
  • Antiperspirant roll-on emulsions commonly comprise one or more emulsifiers to maintain a distribution of the water-soluble ingredients.
  • the antiperspirant composition may be delivered through an aerosol composition which comprises a propellant in addition to the other ingredients described hereinabove.
  • the propellant is employed in a weight ratio to the base formulation of from 95:5 to 5:95.
  • the ratio of propellant to base formulation is normally at least 20:80, generally at least 30:70, particularly at least 40:60, and in many formulations, the weight ratio is from 90:10 to 50:50.
  • a ratio range of from 70:30 to 90:10 is sometimes preferred.
  • Propellants herein generally are one of three classes; i) low boiling point gasses liquefied by compression, ii) volatile ethers and iii) compressed non-oxidising gases.
  • Class i is conveniently a low boiling point material, typically boiling below -5°C, and often below -15°C, and in particular, alkanes and/or halogenated hydrocarbons.
  • This class of propellant is usually liquefied at the pressure in the aerosol canister and evaporates to generate the pressure to expel the composition out of the canister.
  • the second class of propellant comprises a very volatile ether of which the most widely employed ether hitherto is dimethyl ether.
  • This propellant can advantageously be employed at relatively low weight ratio of propellant to base formulation, for example to as low as 5:95. It can also be employed in admixture with, for example,
  • the third class of propellant comprises compressed non-oxidising gasses, and in particular carbon dioxide or nitrogen. Inert gases like neon are a theoretical alternative.
  • the topically acceptable carrier comprises an anhydrous carrier or an aqueous carrier.
  • the anhydrous carrier in such cases may comprise a silicone compound, low boiling alcohol or a wax.
  • the composition comprises a propellant it is delivered as an aerosol.
  • composition of the present invention can comprise a wide range of other optional components.
  • CTFA Personal Care Ingredient Handbook Second Edition, 1992, which is incorporated by reference herein in its entirety, describes a wide variety of non-limiting personal care and pharmaceutical ingredients commonly used in the skin care industry, which are suitable for use in the compositions of the present invention. Examples include: antioxidants, binders, biological additives, buffering agents, colorants, thickeners, polymers, astringents, fragrance, conditioners, exfoliating agents, pH adjusters, preservatives, natural extracts, essential oils, skin sensates, skin soothing agents, and skin healing agents.
  • a preservative is a preferred additional component in compositions of the invention.
  • a preservative serves to reduce or eliminate microbial contamination of compositions of the invention.
  • Preservatives are typically employed at a total level of from 0.05 to 3%, preferably at from 0.1 to 2% and most preferably at from 0.4 to 1%.
  • Suitable preservatives for use with the present invention include 2-phenoxyethanol, iodopropynyl butylcarbamate, C1-C3 alkyl parabens, sodium benzoate, caprylyl glycol and EDTA.
  • Particularly preferred preservatives are 2-phenoxyethanol, iodopropynyl butylcarbamate, sodium benzoate, caprylyl glycol and EDTA and especially preferred are 2-phenoxyethanol and iodopropynyl butylcarbamate.
  • compositions of the invention is a fragrance.
  • Suitable materials include conventional perfumes, such as perfume oils and also include so-called deo-perfumes, as described in EP 545,556 and other publications.
  • Levels of incorporation are preferably up to 4% by weight, particularly from 0.1% to 2% by weight, and especially from 0.7% to 1.7% by weight.
  • An antimicrobial deodorant active is a preferred an additional component in
  • compositions of the invention serve to reduce or eliminate body odour by reducing or otherwise impeding the function of microbes on the skin of the body responsible for malodour generation.
  • the antimicrobial deodorant active may also be a preservative for the composition.
  • the anti-microbial deodorant agent is typically incorporated into the composition at from 0.01% to 3% and particularly at from 0.03% to 0.5%.
  • Preferred anti-microbial deodorant agents have a minimum inhibitory concentration (MIC) of 1 mg. ml 1 or less, particularly 200 pg.mh 1 or less, and especially 100 pg.ml 1 or less.
  • MIC minimum inhibitory concentration
  • the MIC of an anti-microbial agent is the minimum concentration of the agent required to significantly inhibit microbial growth. Inhibition is considered“significant” if an 80% or greater reduction in the growth of an inoculum of Staphylococcus epidermidis is observed, relative to a control medium without an anti-microbial agent, over a period of 16 to 24 hours at 37°C.
  • MlCs of anti-microbials suitable for inclusion in the compositions of the invention are triclosan: 0.01 -10 pg.ml -1 (J.Regos et al , Dermatologies (1979), 158: 72-79) and farnesol: ca. 25 pg.mH (K, Sawano, T.
  • Suitable organic anti-microbials are bactericides, for example quaternary ammonium compounds, like cety!trimethylammonium salts; chlorhexidine and salts thereof; and diglycerol monocaprate, diglycerol monolaurate, glycerol monolaurate, and similar materials, as described in "Deodorant Ingredients”, S.A.Makin and M.R.Lowry, in “Antiperspirants and Deodorants”, Ed, K. Laden (1999, Marcel Dekker, New York).
  • More preferred anti-microbials for use in the compositions of the invention are polyhexamethylene biguanide salts (also known as polyaminopropyl biguanide salts), an example being Cosmocil CQTM available from Zeneca PLC, preferably used at up to
  • ZAA-trichioro ⁇ -hydroxy- diphenyl ether triclosan
  • triclosan 3,7,11 -trimethyldodeca-2,6, 10-trienol
  • farnesol 3,7,11 -trimethyldodeca-2,6, 10-trienol
  • transition metal chelators as described in W001/52805, for example.
  • Transitional metal chelators having a binding coefficient for iron(lll) of greater than 10 26 for example diethylenetriaminepentaacetic acid and salts thereof are preferred.
  • the present invention also provides for a method of reducing perspiration comprising the step of applying the composition of the first aspect on to the desired skin surface.
  • the skin surface could be any topical surface which is prone to sweating especially the axilla i.e. the underarm portion of the human body.
  • the method is preferably non- therapeutic.
  • the invention also provides for use of the zirconium complex where zirconium is chelated by alkanolamine, for manufacture of a composition as claimed in the present invention, for reduction of sweat.
  • the invention also provides for use of a zirconium complex wherein zirconium is chelated by alkanolamine as an antiperspirant active.
  • the use is for therapeutic treatment.
  • the use is for non-therapeutic purposes, particularly for cosmetic purposes.
  • compositions were tested for stability by using the following procedure:
  • compositions could cross-link the polysaccharide in sweat duct and then form a gel.
  • the cross-linked polysaccharide which forms the gel in the sweat ducts would thereby act as antiperspirants.
  • BSA Bovine serum albumin
  • 1% BSA solution was prepared by dissolving BSA in distilled water. Then, 1g Tyzor212 (Example 13) was added into 10ml BSA solution. It was observed that the solution became turbid immediately after mixing Tyzor212 with 1%BSA solution.
  • Examples 14 to 16 Gelation of different zirconium complex in the presence of guar polymer.
  • An antiperspirant composition comprising a zirconium complex as given in Table 4 was prepared according to the description set forth in Example 7 of US Patent No.3407254.
  • the pH of the composition was 3.4 Table 4
  • compositions were prepared as given in Table 5.
  • Table 6 indicates that compositions as per the invention (Examples 14 to 15) at different pH were able to crosslink with the polysaccharide (representing mucin in sweat ducts) and then form a gel to thereby act as antiperspirants, while the other zirconium complex with different structure (Example A) could not form the gel.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne le domaine des compositions anti-transpirantes, en particulier des compositions comprenant des actifs anti-transpirants. La présente invention concerne plus particulièrement des compositions comprenant des actifs anti-transpirants à base de zirconium qui sont stables avant utilisation et efficaces pour assurer des avantages anti-transpirants. Ceci est obtenu par formulation de l'actif anti-transpirant dans une base cosmétiquement acceptable.
PCT/EP2018/081869 2017-12-04 2018-11-20 Composition anti-transpirante comprenant du zirconium WO2019110290A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CN2017114393 2017-12-04
CNPCT/CN2017/114393 2017-12-04
EP18150134 2018-01-03
EP18150134.7 2018-01-03

Publications (1)

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WO2019110290A1 true WO2019110290A1 (fr) 2019-06-13

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021099292A1 (fr) * 2019-11-20 2021-05-27 Unilever Ip Holdings B.V. Composition antiperspirante
US11844853B2 (en) 2018-08-09 2023-12-19 Conopco, Inc. Antiperspirant composition

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Publication number Priority date Publication date Assignee Title
US3407254A (en) 1964-07-24 1968-10-22 Bristol Myers Co Antiperspirant compositions and method for their application
GB1387281A (en) * 1972-01-11 1975-03-12 C A Lab Inc Ultra-violet light absorber compositions
US4650671A (en) 1981-07-17 1987-03-17 Claus Riemann & Co. Aps Antiperspirant kit and method for controlling perspiration
EP0545556A2 (fr) 1991-11-08 1993-06-09 Quest International Nederland Bv Composition parfumante
EP0604988A2 (fr) * 1992-12-29 1994-07-06 Phillips Petroleum Company Compositions gellifiantes utiles pour des gisements petrolifères
WO2001052805A1 (fr) 2000-01-18 2001-07-26 Unilever Plc Compositions antimicrobiennes comprenant un sel d'un chelateur de metal de transition
US20070187642A1 (en) * 2006-02-14 2007-08-16 Putzig Donald E Zirconium cross-linking composition and methods of use
US20090131282A1 (en) * 2007-11-21 2009-05-21 Donald Edward Putzig Solid Zirconium-based cross-linking agent and use in oil field applications
US20090151947A1 (en) * 2007-12-18 2009-06-18 Donald Edward Putzig Process to prepare zirconium-based cross-linker compositions and their use in oil field applications
WO2013116004A1 (fr) * 2012-01-30 2013-08-08 Dow Global Technologies Llc Composition de couche d'apprêt à base d'eau pour le collage de verre dans une structure
US20140073538A1 (en) * 2012-09-12 2014-03-13 Halliburton Energy Services, Inc. Fluid Loss Control Composition and Method of Using the Same
CN106835109A (zh) * 2017-01-18 2017-06-13 帝业化学品（上海）有限公司 环保型金属表面前处理涂层

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3407254A (en) 1964-07-24 1968-10-22 Bristol Myers Co Antiperspirant compositions and method for their application
GB1387281A (en) * 1972-01-11 1975-03-12 C A Lab Inc Ultra-violet light absorber compositions
US4650671A (en) 1981-07-17 1987-03-17 Claus Riemann & Co. Aps Antiperspirant kit and method for controlling perspiration
EP0545556A2 (fr) 1991-11-08 1993-06-09 Quest International Nederland Bv Composition parfumante
EP0604988A2 (fr) * 1992-12-29 1994-07-06 Phillips Petroleum Company Compositions gellifiantes utiles pour des gisements petrolifères
WO2001052805A1 (fr) 2000-01-18 2001-07-26 Unilever Plc Compositions antimicrobiennes comprenant un sel d'un chelateur de metal de transition
US20070187642A1 (en) * 2006-02-14 2007-08-16 Putzig Donald E Zirconium cross-linking composition and methods of use
US20090131282A1 (en) * 2007-11-21 2009-05-21 Donald Edward Putzig Solid Zirconium-based cross-linking agent and use in oil field applications
US20090151947A1 (en) * 2007-12-18 2009-06-18 Donald Edward Putzig Process to prepare zirconium-based cross-linker compositions and their use in oil field applications
WO2013116004A1 (fr) * 2012-01-30 2013-08-08 Dow Global Technologies Llc Composition de couche d'apprêt à base d'eau pour le collage de verre dans une structure
US20140073538A1 (en) * 2012-09-12 2014-03-13 Halliburton Energy Services, Inc. Fluid Loss Control Composition and Method of Using the Same
CN106835109A (zh) * 2017-01-18 2017-06-13 帝业化学品（上海）有限公司 环保型金属表面前处理涂层

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Title
A. BALOWS ET AL: "Manual of Clinical Microbiology, 5th ed", 1991, AMERICAN SOCIETY FOR MICROBIOLOGY, article C. THORNSBERRY ET AL.: "Antimicrobial Agents and Susceptibility Testing"
DATABASE WPI Week 201755, Derwent World Patents Index; AN 2017-51483R, XP002780563 *
J.REGOS ET AL., DERMATOLOGICA, vol. 158, 1979, pages 72 - 79
K. LADEN: "Antiperspirants and Deodorants", 1999, MARCEL DEKKER, article S.A.MAKIN; M.R.LOWRY: "Deodorant Ingredients"
K. SAWANO; T. SATO; R. HATTORI, PROCEEDINGS OF THE 17TH IFSCC INTERNATIONAL CONFERENCE, 1992, pages 210 - 232

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11844853B2 (en) 2018-08-09 2023-12-19 Conopco, Inc. Antiperspirant composition
WO2021099292A1 (fr) * 2019-11-20 2021-05-27 Unilever Ip Holdings B.V. Composition antiperspirante

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