WO2012076309A1 - Composition antimicrobienne capable de former une suspension turbide lors de sa dilution avec de l'eau - Google Patents

Composition antimicrobienne capable de former une suspension turbide lors de sa dilution avec de l'eau Download PDF

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Publication number
WO2012076309A1
WO2012076309A1 PCT/EP2011/070314 EP2011070314W WO2012076309A1 WO 2012076309 A1 WO2012076309 A1 WO 2012076309A1 EP 2011070314 W EP2011070314 W EP 2011070314W WO 2012076309 A1 WO2012076309 A1 WO 2012076309A1
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WO
WIPO (PCT)
Prior art keywords
composition
water
surfactant
dilution
disinfecting
Prior art date
Application number
PCT/EP2011/070314
Other languages
English (en)
Inventor
Bharat Cheviti
Kalpana Kamalakar Nayak
Deeleep Kumar Rout
Original Assignee
Unilever Nv
Unilever Plc
Hindustan Unilever Limited
Sinha, Ritesh Kumar
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, Unilever Plc, Hindustan Unilever Limited, Sinha, Ritesh Kumar filed Critical Unilever Nv
Publication of WO2012076309A1 publication Critical patent/WO2012076309A1/fr

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Classifications

    • 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
    • A61Q17/005—Antimicrobial preparations
    • 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
    • A61K8/068—Microemulsions
    • 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
    • A61K8/34—Alcohols
    • 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
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • 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
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • 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
    • A61K8/18—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
    • A61K8/37—Esters of carboxylic acids
    • 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
    • A61K8/416—Quaternary ammonium compounds
    • 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
    • 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
    • A61K2800/26—Optical properties
    • A61K2800/262—Transparent; Translucent

Definitions

  • the invention relates to transparent/translucent liquid
  • Hygiene has been and continues to be one of the most important requirements among consumers. Consumers all over the world use different types of antimicrobial compositions for disinfecting various surfaces like hard surfaces in the homes, factories and offices e.g. kitchen tops, floors and furniture; soft and porous surfaces like clothes, carpets and upholstery; and personal surfaces like skin and hair.
  • E. coli Escherichia coli
  • S. aureus Staphylococcus aureus
  • hypochlorite salts sodium hypochlorite salts.
  • hypochlorite causes bad smell, bleaches clothes that come in contact with it and is unpleasant to skin which is mostly caused by its high alkalinity.
  • Surfactant based detergent compositions are often used to clean soft surfaces like fabrics and such compositions often include bleaches like peroxides. For personal hygiene, soap is often used for disinfecting skin. Many of the above compositions are considered harsh and
  • class of liquid disinfectants This is a class of products where the compositions are predominantly water or a mix of water and solvents with a small amount of disinfectants which may synthetic or naturally derived.
  • Such products comprising naturally derived disinfectants e.g. essential oils are
  • Such natural actives like essential oils are insoluble in water and have to be formulated in water with the aid of emulsifiers which lead to a composition which is opaque or turbid and kinetically unstable. Providing such a composition in a
  • Formation of a turbid suspension or cloudiness on dilution to the desired level is often achieved using high concentration of essential oils e.g. pine oil at concentrations higher than 3% is known to bloom when diluted with water.
  • compositions where the antimicrobial agents like essential oils are used at low concentrations which not only cause blooming on dilution with water but ensures the desired anti-microbial action at such low concentrations.
  • the present inventors have been working on solving this problem of providing such a disinfectant composition that is
  • the present invention provides a solution to the above problem by way of incorporating the antimicrobial agents in low
  • a specific microemulsion composition that comprises selective amount of a surfactant, an specified class of organic solvents and a clouding agent selected from fatty acid, or alkyl ester of fatty acid that ensures solubility of the antimicrobial agents oils in the composition thus ensuring a transparent appearance when stored and transported and gives a turbid/cloudy appearance when diluted with water, to provide a visual cue to the consumer about the delivery of the
  • the turbidity is ensured in short time span after the composition is diluted with water.
  • compositions comprising some of the above components with such essential oils in either a microemulsion or emulsion format have been reported viz. US5591708, US2005107278, US2009281012, US2006084589 and US5486307.
  • the compositions reported in these publications do not have all of the constituents of the present invention thereby unable to provide either the transparent appearance or the turbid appearance on dilution with water.
  • GB 2320927 discloses a blooming type, germicidal hard surface cleaning and disinfecting concentrate composition which
  • a terpene containing solvent which desirably includes both pine oil and d-limonene
  • a non-ionic surfactant constituent which desirably includes at least one non-ionic surfactant which exhibits a cloud point in water of less than 20 °C
  • a amphoteric surfactant selected from imidazoline and amino propionate surfactants; at least one germicidal cationic surfactant; and water.
  • the blooming in the above patent publication is achieved due to the high concentration of the essential oil viz. pine oil constituent . It is thus an object of the present invention to provide for an anti-microbial composition that has a clear transparent / translucent appearance and becomes turbid on dilution with water .
  • the first aspect of the present invention provides for a transparent/ translucent liquid antimicrobial composition in microemulsion format capable of forming turbid suspension on dilution with water comprising
  • an antimicrobial active selected from the class comprising terpenes, essential oils, or cationic oils having a solubility in water of less than 2000 ppm at 25°C;
  • a clouding agent selected from the class comprising C8 to C22 fatty acid or alkyl esters of fatty acids.
  • the second aspect of the present invention provides for use of a composition of the first aspect of the present invention for disinfecting external surfaces of human or animal body, for disinfecting soft and porous substrates like fabric or for disinfecting hard surfaces.
  • the third aspect of the present invention provides for a method of disinfecting a surface comprising the steps of
  • composition of the invention may be formulated in any product primarily for disinfecting surfaces but may also be formulated in products that also provide other benefits like cleansing, odor control or general aesthetics.
  • the composition of the present invention is generally in the form of a liquid but may be thickened to a gel.
  • Non-limiting examples of compositions include disinfectant liquids, shampoos,
  • the invention provides for a transparent/translucent liquid antimicrobial composition in microemulsion format capable of forming turbid suspension on dilution with water comprising a selective antimicrobial active, a surfactant, a selective organic solvent, a selective clouding agent and water.
  • the microemulsion composition of the invention is preferably transparent. This format of the composition is especially preferred since the transparent form makes for an appealing visual impact on consumers.
  • the dispersed phase droplets in the microemulsion are in the size range of 6 to 50 nm, more preferably in the size range of 6 to 15 nm .
  • the antimicrobial agent is selected from the class comprising terpenes, essential oils, or cationic oils having a solubility in water of less than 2000 ppm at 25°C. Examples of aromatic essential oils suitable for use in the present invention include amyl salicylate, carvacrol, cymene, e.g.
  • non-aromatic essential oils of terpenoid compounds include cedrene, cineole, citral (including geranial and neral), citronellal, citronellol, eucalyptol (also known as 1,8
  • cineole paradihydrolinalool , dihydromyrcenol (DH myrcenol), farnesol, geraniol, hexyl cinnamaldehyde, hydroxycitronallol , hydroxycitronellal , isocitral, limonene, preferably d-limonene, linalool, longifolene, menthol, nerol, nerolidiol, pinene, e.g. -pinene, phellendrene, terpinene, e.g. -terpinene and
  • ⁇ -terpinene terpineol, e.g. ⁇ -terpineol and terpin-4-ol, and tetrahydromyrcenol (THM) .
  • Preferred cationic oils include
  • the solubility of the antimicrobial active is less than 2000 ppm at 25°C. More preferred antimicrobial actives are terpineol, thymol, eugenol, borneol or limonene and mixtures thereof. Further more preferred antimicrobial actives are terpineol, thymol or eugenol. An especially preferred
  • composition comprises thymol and terpineol.
  • An even further preferred composition comprises thymol, terpineol and eugenol.
  • the antimicrobial active is present in 0.05 to 2%, more
  • microemulsion preferably 0.1 to 2% by weight of the microemulsion
  • the microemulsion composition of the invention comprises 0.05 to 10%, preferably 0.05 to 8 %, more preferably 0.5 to 5% surfactant by weight of the composition.
  • the surfactant is preferably of the cationic, anionic, or zwitterionic class. Cationic or anionic surfactant is more preferred, most
  • anionic surfactant is present it is preferably chosen from alkali or alkaline earth metal salts of alkyl sulphonic acid, fatty acid, or alkyl ether sulphate.
  • zwitterionic surfactant is present it is
  • surfactant is present, it is preferably benzalkonium chloride, alkyl pyridinium chloride or quaternary ammonium gemini
  • the microemulsion composition of the invention comprises 1 to 50% of an organic solvent selected from linear or branched alcohol having a Log P value in the range of -1.5 to 3.
  • Log P is a property defined in the article Hiroshi Chuman, Atsushi Mori and Hideji Tanaka, "Prediction of the 1-Octanol/H20
  • Log P is basically the 1-octanol/water partition coefficient and is experimentally determined by the shake-flask method.
  • Preferred alcohols have a carbon chain length of 1 to 7. Examples of such organic solvents are ethyl alcohol, isopropyl alcohol, octanol, or propyl alcohol.
  • the useful alcohols and their log P values are given in Table below. Alcohol log P at 25°C Vapour Pressure
  • Preferred organic solvents have a log P value from -0.1 to 3. Most preferred alcohols are ethyl alcohol or isopropyl alcohol.
  • the solvent used in the microemulsion composition of the invention preferably has a vapor pressure greater than or equal to 0.05 mm Hg at 25°C.
  • the organic solvent is preferably present in 1 to 45%, more preferably 1 to 30 % by weight of the composition .
  • a selective clouding or blooming agent is included in the microemulsion composition of the invention.
  • the clouding agent has to be carefully selected such that the microemulsion stability and concomitant transparency are not compromised while ensuring the desired quick precipitation when diluted with water.
  • the clouding agent is selected from the class comprising C8 to C22 fatty acid or alkyl esters of fatty acids. Preferred clouding agents have carbon chain length 8 to 22 more
  • the clouding agent is preferably present in 0.5 to 10 %, more preferably in 0.5 to 5% by weight of the composition. Clouding agent preferably has a melting point greater than 25°C. The clouding agent preferably has a solubility in water of less than 2000 ppm in water at 25°C.
  • the composition of the invention preferably comprises 40 to 99%, preferably 50 to 80%, further more preferably 50 to 70 % water by weight of the composition.
  • Suitable electrolyte may be chosen from a chloride, sulphate, acetate, or carbonante of an alkali, alkaline earth or transition metal. Of these, multivalent electrolyes are especially preferred.
  • electrolytes include chloride, sulphate or acetate of an alkaline earth metal.
  • electrolytes useful in including in the composition of the invention are calcium chloride, sodium chloride, magnesium chloride, zinc sulphate, aluminium chloride or zinc acetate. The more preferred
  • electrolytes are calcium chloride, magnesium chloride, zinc sulphate or zinc acetate while the most preferred electrolytes are zinc sulphate or zinc acetate.
  • Electrolyte is preferably present in 0.005 to 10%, more preferably 0.05 to 10 %, further more preferably 0.05 to 5 % by weight of the composition.
  • the inclusion of the electrolyte in the microemulsion composition of the invention allows for meeting all of the objects of the invention while minimizing the amount of solvent to be used.
  • microemulsion composition of the invention is usually to be used for disinfecting a surface by first diluting the
  • composition water for the dilution step is in the range of 1:1 to 1:200, more preferably 1:5 to 1:50 and optimally 1:15 to 1:30 and ideally about 1:20.
  • composition has a turbidity value of 0 to 200 NTU.
  • turbidity increases to greater than 500 NTU in less than 5 seconds, preferably less than 2 seconds, more preferably less than 1 second, most preferably immediately after the dilution step .
  • composition of the invention preferably has a pH ranging from 3 to 8, more preferably from 3.5 to 8 at 25°C.
  • a method of disinfecting a surface comprising the steps of (i) applying the composition of the invention to a desired surface followed by (ii) removing the composition from the surface after a predetermined time period.
  • the composition is
  • Suitable surfaces for disinfecting include external surfaces of human or animal body and soft and porous substrates like fabric and hard surfaces. More suitable surfaces include animate surfaces like the external surfaces of animal or human body e.g. skin and hair or inanimate surfaces like hard surfaces e.g. floors, furniture, kitchen tops, utensils and soft/porous surfaces e.g. clothes/ fabric, carpets or upholstery.
  • the composition/ diluted composition is then removed from the disinfected surface.
  • removing is meant that it is wiped off from the surface using a suitable material or implement e.g. a sponge, fabric or a wipe.
  • a suitable material or implement e.g. a sponge, fabric or a wipe.
  • the composition/ diluted composition is rinsed off from the surface using desired amount of water.
  • the predetermined time for removing the composition from the surface may vary according to the amount of cleanliness desired and the type of surface but may vary from 5 to 3000 seconds, preferably 15 to 120 seconds.
  • use of the composition of the invention for disinfecting external surfaces of human or animal body, for disinfecting soft and porous substrates like fabric or for disinfecting hard surfaces.
  • the use is preferably non-therapeutic.
  • Examples 1 to 7 Comparison of the antibacterial efficacy and desired turbidity of compositions as per the invention as compared to a composition out side the invention.
  • Table -1 The following compositions, as shown in Table -1 were prepared. The number presented are in % by weight of the composition. Table - 1:
  • composition was tested for the following desired
  • compositions were tested for antibacterial kill using the following protocol.
  • Organism E. coli,
  • compositions were tested to check if the desired turbidity was attained on diluting the composition.
  • the test procedure used was as follows.
  • compositions 1 to 7 is summarized in Table - 2.
  • the efficacy passed the criterion of 5 log kill of bacteria the sample is evaluated as Yes' . If the turbidity passed the criterion of >800 NTU, the sample was evaluated as Yes' , else as ⁇ ⁇ ' .
  • compositions as per the invention were prepared as shown in Table - 3.
  • Example Example- 8 Example- 9, Example- 10, wt% wt% wt%
  • compositions of Table -3 exhibited the desired anti ⁇ bacterial efficacy and turbidity on dilution.
  • the invention thus provides for an anti-microbial composition comprising natural actives that has a clear transparent / translucent appearance and becomes turbid on dilution with water, in very quick time.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dispersion Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne une composition antimicrobienne liquide transparente/translucide qui comprend des désinfectants d'origine naturelle. L'incorporation de ces désinfectants dans une composition aqueuse tout en conservant une grande transparence/translucidité est un défi. Qui plus est, ces compositions sont commercialisées sous forme de concentrés et le consommateur doit les diluer avec de l'eau avant l'utilisation. Il est avantageux de fournir un repère visuel de turbidité lors de la dilution pour indiquer au consommateur que la dilution souhaitée est atteinte. La présente invention propose une solution au problème ci-dessus par l'incorporation d'agents antimicrobiens dans une composition de microémulsion spécifique qui assure une apparence transparente lors du stockage et du transport et prend une apparence turbide/trouble lors de la dilution avec de l'eau. La turbidité apparaît rapidement après la dilution de la composition avec de l'eau.
PCT/EP2011/070314 2010-12-07 2011-11-17 Composition antimicrobienne capable de former une suspension turbide lors de sa dilution avec de l'eau WO2012076309A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN3320/MUM/2010 2010-12-07
IN3320MU2010 2010-12-07
EP11151946 2011-01-25
EP11151946.8 2011-01-25

Publications (1)

Publication Number Publication Date
WO2012076309A1 true WO2012076309A1 (fr) 2012-06-14

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013192382A3 (fr) * 2012-06-21 2014-09-04 The Procter & Gamble Company Émulsions de bain de bouche
CN105360113A (zh) * 2015-12-04 2016-03-02 兰州交通大学 增效农药微乳剂的制备方法
WO2021180909A1 (fr) * 2020-03-13 2021-09-16 Unilever Ip Holdings B.V. Composition de nettoyage
CN115279878A (zh) * 2020-03-13 2022-11-01 联合利华知识产权控股有限公司 清洁组合物
WO2023025575A1 (fr) * 2021-08-26 2023-03-02 Unilever Ip Holdings B.V. Composition de désinfection liquide

Citations (9)

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Publication number Priority date Publication date Assignee Title
US5486307A (en) 1993-11-22 1996-01-23 Colgate-Palmolive Co. Liquid cleaning compositions with grease release agent
US5591708A (en) 1995-08-04 1997-01-07 Reckitt & Colman Inc. Pine oil hard surface cleaning compositions
GB2320927A (en) 1997-01-06 1998-07-08 Reckitt & Colman Inc Germicidal hard surface cleaner
WO1999058631A1 (fr) * 1998-05-11 1999-11-18 The Clorox Company Nettoyant pouvant etre dilue dans une micro-emulsion
US6177388B1 (en) * 1998-04-14 2001-01-23 Reckitt Benckiser Inc. Botanical oils a blooming agents in hard surface cleaning compositions
WO2003091375A1 (fr) * 2002-04-23 2003-11-06 Reckitt Benckiser Inc Compositions desinfectantes et nettoyantes
US20050107278A1 (en) 2003-11-19 2005-05-19 Clariant International, Ltd. Blooming natural oil cleaning compositions
US20060084589A1 (en) 2004-10-20 2006-04-20 Vlad Florin J Solubilizing systems for flavors and fragrances
US20090281012A1 (en) 2008-05-09 2009-11-12 Rhodia Inc. Cleaning compositions incorporating green solvents and methods for use

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5486307A (en) 1993-11-22 1996-01-23 Colgate-Palmolive Co. Liquid cleaning compositions with grease release agent
US5591708A (en) 1995-08-04 1997-01-07 Reckitt & Colman Inc. Pine oil hard surface cleaning compositions
GB2320927A (en) 1997-01-06 1998-07-08 Reckitt & Colman Inc Germicidal hard surface cleaner
US6177388B1 (en) * 1998-04-14 2001-01-23 Reckitt Benckiser Inc. Botanical oils a blooming agents in hard surface cleaning compositions
WO1999058631A1 (fr) * 1998-05-11 1999-11-18 The Clorox Company Nettoyant pouvant etre dilue dans une micro-emulsion
WO2003091375A1 (fr) * 2002-04-23 2003-11-06 Reckitt Benckiser Inc Compositions desinfectantes et nettoyantes
US20050107278A1 (en) 2003-11-19 2005-05-19 Clariant International, Ltd. Blooming natural oil cleaning compositions
US20060084589A1 (en) 2004-10-20 2006-04-20 Vlad Florin J Solubilizing systems for flavors and fragrances
US20090281012A1 (en) 2008-05-09 2009-11-12 Rhodia Inc. Cleaning compositions incorporating green solvents and methods for use

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
HIROSHI CHUMAN; ATSUSHI MORI; HIDEJI TANAKA: "Prediction of the 1-Octanol/H20 Partition Coefficient, Log P, by Ab Initio MO Calculations: Hydrogen-Bonding Effect of Organic Solutes on Log P", ANALYTICAL SCIENCES, vol. 18, September 2002 (2002-09-01), pages 1015 - 1020

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013192382A3 (fr) * 2012-06-21 2014-09-04 The Procter & Gamble Company Émulsions de bain de bouche
CN104411290A (zh) * 2012-06-21 2015-03-11 宝洁公司 漱口水乳液
AU2013277105B2 (en) * 2012-06-21 2016-07-21 The Procter & Gamble Company Mouth rinse emulsions
RU2648461C2 (ru) * 2012-06-21 2018-03-26 Дзе Проктер Энд Гэмбл Компани Эмульсии для полоскания полости рта
CN105360113A (zh) * 2015-12-04 2016-03-02 兰州交通大学 增效农药微乳剂的制备方法
WO2021180909A1 (fr) * 2020-03-13 2021-09-16 Unilever Ip Holdings B.V. Composition de nettoyage
CN115209731A (zh) * 2020-03-13 2022-10-18 联合利华知识产权控股有限公司 清洁组合物
CN115279878A (zh) * 2020-03-13 2022-11-01 联合利华知识产权控股有限公司 清洁组合物
WO2023025575A1 (fr) * 2021-08-26 2023-03-02 Unilever Ip Holdings B.V. Composition de désinfection liquide

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