EP2844349A1 - Polymères de sels de méthacrylate d'éthyle et d'ammonium quaternaire trialkyle en tant qu'exhausteurs de crissement dans des compositions de nettoyage - Google Patents

Polymères de sels de méthacrylate d'éthyle et d'ammonium quaternaire trialkyle en tant qu'exhausteurs de crissement dans des compositions de nettoyage

Info

Publication number
EP2844349A1
EP2844349A1 EP13716005.7A EP13716005A EP2844349A1 EP 2844349 A1 EP2844349 A1 EP 2844349A1 EP 13716005 A EP13716005 A EP 13716005A EP 2844349 A1 EP2844349 A1 EP 2844349A1
Authority
EP
European Patent Office
Prior art keywords
composition according
homopolymer
squeakiness
polymers
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.)
Withdrawn
Application number
EP13716005.7A
Other languages
German (de)
English (en)
Inventor
Jean-Philippe Andre Roger Courtois
Junqi Ding
Chandra Sekhar PALLA-VENKATA
Jane Whittaker
Surajit Mukherjee
Rajendra Mohanlal Dave
Adam Peter Jarvis
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 PLC
Unilever NV
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
Publication of EP2844349A1 publication Critical patent/EP2844349A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • 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
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines

Definitions

  • the present invention relates to skin and hair cleansing compositions in toilet bar, body wash, liquid hand cleanser, shampoo and related products.
  • GB 2 104 091 A discloses detergent compositions which include an amphoteric copolymer obtained by co-polymerizing an anionic vinyl monomer having a polymerizable unsaturated group with a cationic vinyl monomer also having a polymerizable unsaturated group.
  • DMAEMA dimethylaminoethylmethacrylate
  • a cleanser composition which includes:
  • composition exhibits a Squeakiness SQ1 value ranging from 5 to 100 grams as measured in an Acoustic Tribometer Tester.
  • trimethylammonium ethyl methacrylate salts can add squeakiness to the feel of non- soap-surfactant containing cleansing systems while not detracting from mildness. Squeakiness has been correlated by us to the output from an Acoustic Tribometer Tester. This instrument measures the friction coefficient of liquid systems during surfactant wash-off via a finger vibration device. After the first application and rinse off of sample to a skin area, the application should exhibit
  • a Squeakiness SQ1 value ranging from 5 to 100, usually between 10 and 90, particularly between 23 and 80, and especially between 30 and 80 grams as measured at 34 degrees C and an instrument speed of 17 mm/seconds.
  • the squeakiness enhancing homopolymers of the present invention are formed from monomer units having the structure (I):
  • X " is an anion selected from the group consisting of chloride, bromide, hydroxyl, sulphate, phosphate, methosulphate, carboxyl, citrate and tartrate. Most preferred as X " is chloride.
  • Amount of the homopolymer may range from 0.01 to about 2%, preferably from 0.1 to about 1 %, more preferably from about 0.3 to about 1 %, and optimally from about 0.3 to about 0.8% by weight of the composition.
  • Polymers of this invention are homopolymers.
  • the homopolymers may be cross-linked with polyvinyl crosslinking monomers.
  • the homopolymers may have a number average molecular weight ranging from 10,000 to 1 million, preferably from 10,000 to 800,000, more preferably from 15,000 to 500,000, and optimally from 20,000 to 300,000 Dalton. Most preferred is a homopolymer of structure (I) with a number average molecular weight ranging from about 30,000 to about 100,000 Dalton.
  • the crosslinking agents are not limited, and may be chosen for example from the polyolefinically unsaturated compounds commonly used for crosslinking polymers obtained by free-radical polymerization.
  • crosslinking agents examples include divinylbenzene, diallyl ether, dipropylene glycol diallyl ether, polyglycol diallyl ethers, triethylene glycol divinyl ether, hydroquinone diallyl ether, ethylene glycol or tetraethylene glycol di(meth)acrylate, trimethylolpropane triacrylate, methylenebisacrylamide, methylenebismethacrylamide, triallylamine, triallyl cyanurate, diallyl maleate, tetraallylethylenediamine, tetraallyloxyethane,
  • the crosslinking agent is chosen from methylenebisacrylamide, allyl methacrylate and trimethylolpropane triacrylate (TMPTA).
  • TMPTA trimethylolpropane triacrylate
  • the degree of crosslinking is not limited, but generally may range from 0.01 mol % to 10 mol % and more particularly from 0.2 mol % to 2 mol % relative to the polymer.
  • Another component of compositions disclosed herein is non-soap synthetic foaming surfactants. These may be selected from anionic, cationic, amphoteric and combination surfactants thereof. Amounts may range from 0.1 to about 30%, preferably from about 1 to about 20%, and optimally from about 3 to about 15% by weight of the composition.
  • Suitable amphoteric surfactants for use herein include, but are not limited to, derivatives of aliphatic quaternary ammonium, phosphonium, and sulfonium compounds, in which the aliphatic radicals can be straight or branched chain, and wherein one of the aliphatic substituents contains from about 8 to about 18 carbon atoms and one substituent contains an anionic group, e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate.
  • Illustrative amphoterics are coco dimethyl carboxymethyl betaine, cocoamidopropyl betaine, cocobetaine, oleyl betaine, cetyl dimethyl carboxymethyl betaine, lauryl bis-(2-hydroxyethyl) carboxymethyl betaine, stearyl bis-(2-hydroxypropyl) carboxymethyl betaine, oleyl dimethyl gamma- carboxypropyl betaine, lauryl bis-(2-hydroxypropyl)alpha-carboxyethyl betaine, cocoamphoacetates, and mixtures thereof.
  • the sulfobetaines may include stearyl dimethyl sulfopropyl betaine, lauryl dimethyl sulfoethyl betaine, lauryl bis-(2- hydroxyethyl) sulfopropyl betaine and mixtures thereof. Most preferred is cocoamidopropyl betaine.
  • the anionic surfactant may be, but is not limited to, C 8 -C 2 2 alkane sulfates, ether sulfates and sulfonates.
  • suitable sulfonates are primary C 8 -C 2 2 alkane sulfonate, primary C 8 -C 2 2 alkane disulfonate, C 8 -C 2 2 alkene sulfonate, C 8 -C 2 2 hydroxyalkane sulfonate or alkyl glyceryl ether sulfonate.
  • anionic surfactants suitable for use herein include ammonium lauryl sulfate, ammonium laureth sulfate, triethylamine lauryl sulfate, triethylamine laureth sulfate, triethanolamine lauryl sulfate, triethanolamine laureth sulfate, monoethanolamine lauryl sulfate, monoethanolamine laureth sulfate,
  • An especially useful anionic surfactant is the ammonium or alkali metal salt of laureth sulfate having a degree of ethoxylation ranging from 0.5 to 1.5 moles, preferably from 0.8 to 1.2 moles, and optimally average of about 1 mole of ethoxylation per unit of hydrophobe (i.e. lauryl sulfate).
  • Suitable glycinate salts include sodium cocoylglycinate, potassium cocoylglycinate, sodium lauroylglycinate, potassium lauroylglycinate, sodium myristoylglycinate, potassium myristoylglycinate, sodium palmitoylglycinate, potassium palmitoylglycinate, sodium stearoylglycinate, potassium
  • Cationic counterions to form the salt of an anionic surfactant may, for illustrative purposes only, be selected from sodium, potassium, ammonium, alkanolammonium and mixtures of these cations.
  • Nonionic surfactants which may be used include the reaction products of compounds having a hydrophobic group and a reactive hydrogen atom.
  • Exemplative are alcohols, acids, amides or alkyl phenols reacted with alkylene oxides, especially ethylene oxide either alone or with propylene oxide.
  • Specific nonionics are C 6 -C 2 2 alkyl phenols-ethylene oxide condensates, the condensation products of C 8 -Ci8 aliphatic primary or secondary linear or branched alcohols with ethylene oxide, and products made by condensation of ethylene oxide with the reaction products of propylene oxide and ethylenediamine.
  • Other nonionics include long chain tertiary amine oxides, long chain tertiary phosphine oxides and dialkyl sulphoxides. Also useful are the alkyl polysaccharides.
  • Surfactants should be chosen which will allow the compositions to have a SITA Foam Test Value ranging from 200 to 800, preferably from 300 to 700, and optimally between 400 and 600 ml.
  • SITA Foam Tester R-2000 Model from the Future Digital Scientific Corp. is normally utilized for this evaluation. The
  • experimental protocol includes loading 10 g of product (no pre-dilution) into a measuring cylinder. Thereinto is added 250 ml water at 40-45° C. The foam volume is that recorded after stirring the sample for 30 seconds at 1000 rpm using a rotor. Final foam volume is obtained as the average of ten repeats of measuring the foam volume upon stirring the sample for the 30 seconds at 1000 rpm.
  • the C 8 -C 2 2 fatty acids optionally may also be included in compositions of this invention.
  • Suitable fatty acids are lauric acid, myristic acid, palmitic, stearic, oleic, linoleic, behenic and acid combinations thereof.
  • Particularly useful are the Ci 2 -Ci 4 fatty acids such as lauric acid and myristic acid.
  • Amounts of the fatty acid when present may range from 0.1 to 15%, preferably from 0.5 to 10%, and optimally from 1 to 5% by weight of the composition.
  • Also useful components of the composition may be the C 8 -C 2 2 fatty alcohols.
  • Suitable fatty alcohols are lauryl alcohol, myristyl alcohol, cetearyl alcohol, stearyl alcohol, oleyl alcohol, linoleyl alcohol, behenyl alcohol and mixtures thereof.
  • Amounts of the fatty alcohol when present may range from 0.1 to 15%, preferably from 0.5 to 10%, and optimally from 1 to 5% by weight of the composition.
  • Water may be present in the compositions in amounts from 5 to 95%, preferably from 50 to 90%, and optimally from 65 to 85% by weight.
  • Water soluble/dispersible polymers are an optional ingredient that may be included in the compositions. These polymers can be cationic, anionic, amphoteric or nonionic types. They are known to increase the viscosity and stability of liquid cleanser compositions, to enhance in-use and after-use skin sensory feels, and to enhance lather creaminess and lather stability. Amount of the polymers when present may range from 0.1 to 10% by weight of the composition.
  • water soluble/ or dispersible polymers include the carbohydrate gums such as cellulose gum, microcrystalline cellulose, cellulose gel, hydroxyethyl cellulose, hydroxypropyl cellulose, sodium carboxymethylcellulose, methyl cellulose, ethyl cellulose, guar gum, gum karaya, gum tragacanth, gum arabic, gum acacia, gum agar, xanthan gum and mixtures thereof; modified and nonmodified starch granules and pregelatinized cold water soluble starch; emulsion polymers such as Aculyn® 28, Aculyn® 22 or Carbopol ⁇ Aqua SF1 ; cationic polymer such as modified polysaccharides including cationic guar available from Rhodia under the trade name Jaguar C13S, Jaguar C14S, Jaguar C17, or Jaguar C16; cationic modified cellulose such as UCARE Polymer JR 30 or JR 40 from Amerchol; N- Hance® 3000, N-Hance®
  • Polyquaternium-24 Also suitable are high molecular weight polyethylene glycols such as Polyox® WSR-205 (PEG 14M), Polyox® WSR-N-60K (PEG 45), and Polyox@ WSR-301 (PEG 90 M).
  • high molecular weight polyethylene glycols such as Polyox® WSR-205 (PEG 14M), Polyox® WSR-N-60K (PEG 45), and Polyox@ WSR-301 (PEG 90 M).
  • Water-soluble skin benefit agents may optionally be formulated into the
  • compositions A variety of water-soluble skin benefit agents can be used and the level can be from 0.1 to 50% but preferably from 1 to 30% by weight of the composition. These materials include, but are not limited to, polyhydroxy alcohols. Preferred water soluble skin benefit agents are glycerin, sorbitol and polyethylene glycol.
  • Water-insoluble skin benefit agents may also be formulated into the compositions as conditioners and moisturizers.
  • conditioners and moisturizers examples include silicone oils;
  • hydrocarbons such as liquid paraffins, petrolatum, microcrystalline wax, and mineral oil
  • vegetable triglycerides such as sunflowerseed and cottonseed oils.
  • Preservatives can desirably be incorporated into the compositions to protect against the growth of potentially harmful microorganisms.
  • Suitable traditional preservatives for compositions are alkyl esters of para-hydroxybenzoic acid.
  • Other preservatives which have more recently come into use include hydantoin derivatives, propionate salts, and a variety of quaternary ammonium compounds.
  • Particularly preferred preservatives are phenoxyethanol, methyl paraben, propyl paraben, imidazolidinyl urea, sodium dehydroacetate and benzyl alcohol.
  • the preservatives should be selected having regard for the use of the composition and possible incompatabilities between the preservatives and other ingredients.
  • Preservatives are preferably employed in amounts ranging from 0.01 % to 2% by weight of the composition.
  • compositions may be formulated into the compositions.
  • antimicrobials such as 2-hydroxy-4,2',4'-trichlorodiphenylether (triclosan), 2,6-dimethyl-4-hydroxychlorobenzene, and 3,4,4'-trichlorocarbanilide
  • scrub and exfoliating particles such as polyethylene and silica or alumina
  • cooling agents such as menthol
  • skin calming agents such as aloe vera
  • colorants such as colorants.
  • compositions of the invention may further include 0.5 to 10% by weight of sequestering agents, such as tetra sodium ethylenediaminetetraacetate (EDTA), EHDP or mixtures; opacifiers and pearlizers such as ethylene glycol distearate, titanium dioxide or Lytron 621 (Styrene/Acrylate copolymer); all of which are useful in enhancing the appearance or properties of the product.
  • sequestering agents such as tetra sodium ethylenediaminetetraacetate (EDTA), EHDP or mixtures
  • opacifiers and pearlizers such as ethylene glycol distearate, titanium dioxide or Lytron 621 (Styrene/Acrylate copolymer); all of which are useful in enhancing the appearance or properties of the product.
  • the Figure is a close-up view of key aspects of the Acoustic Tribometer Tester instrument. These aspects include a sample stage (2), load cells (4, 6), a finger vibration device (8), an accelerometer (10), a support table (12), a position guider (14), a photosensor (16), hydrophone (18) and (not shown) a motor and limits which are at the end of position guider.
  • the motor drives a rotary stage through a time- belt (not shown) which can damp the vibration noise from the motor rotation.
  • the sample stage which is immersed into water is connected to the table by two load cells (Honeywell AL31 1AR, 1000g range) which can sense the vertical loads from DC to the frequency of 300Hz.
  • a hydrophone (B&K 1803 hydrophone) is used to detect the underwater sound generated from the stationary sample substrate and the moving artificial finger.
  • an accelerometer (PCB 352A24) is mounted just above water to detect the vibration of the artificial finger.
  • An electromagnetic coil attached to the artificial finger makes it possible to apply finger load during rubbing of the substrate, and to lift up during reverse movement by reversing the voltage applied to the coil.
  • the pivot in the artificial finger provides freedom to respond to the stick-slip generated during sliding through the test surface. The limit of the lift force constrains the length of the artificial finger, and therefore, constrains the water depth of the submerged sample stage.
  • a large tank of water is used (50-53 liters).
  • a photosensor with the position guider is used to generate a "gate" signal where the "low to high” transition relates to the contact position at the right post in the sample stage and the "high to low” transition relates to the contact position at the left post.
  • An electromagnetic relay system (USB- ERB24, Measurement Computing, Inc) is controlled by computer to switch between applying the finger loads (during the sliding) or lifting the finger (during the reverse movement). Further details on many aspects of the instrumentation can be found in EP1684631 B1 herein incorporated by reference.
  • sample stage is removed from the water by lowering the water bath, and 0.25 gms of test composition is applied to the substrate (e.g. synthetic skin).
  • substrate e.g. synthetic skin
  • the sample stage is then placed back into the water by raising the water tank.
  • sample test compositions are rubbed 40 times against the surface with the artificial finger. The latter has a surface of the same substrate as on the sample stage.
  • test composition samples can depend on water hardness.
  • calcium chloride and magnesium chloride are used to adjust the testing water.
  • the ratio of calcium to magnesium is placed in the range from 3:1 to 4:1.
  • Water temperature is adjusted by mixing the hot and cold water.
  • the total amount of water in the tank for a test is around 14 gallons (about 53 liters). Swivelling Speed
  • the swivelling speed of the artificial finger can be fixed at 10 to 100 mm/s, but for the purposes of this invention is maintained at 17 mm/s. Friction Coefficient
  • the setup with two normal load cells creates a system which can measure normal force and friction coefficient.
  • the signal of load cell (4) and load (6) oscillates as the stick-slip generates the normal forces.
  • the two load cells have the same phase in the oscillation and the sum of the two signals provides the amplitude of the stick-slip event.
  • the Squeakiness parameter SQ1 is based on the average deviation of the normal forces for 40 rubs of the first application.
  • the normal force is the force applied through the artificial finger minus the dissipation on the friction.
  • SQ1 is the average of all 40 rubs of the rinse while the swiveling speed is 17 mm/s. This is a good indication for the squeakiness.
  • DMAEMA Dimethylaminoethyl methacrylate
  • ACVA 4,4'-Azobis(4-cyanovaleric acid)
  • IPA Isopropyl alcohol
  • the reaction mixture was heated and stirred at 75 Q C for 4 hrs.
  • the IPA was evaporated and residual monomer was removed by ultrafiltration.
  • the poly( DMAEMA quat) was isolated via freeze drying as a white solid (9.0 g).
  • test compositions were prepared. The formulas of these test compositions and their Squeakiness SQ1 values are outlined in Table l-ll.
  • the poly(trimethylammonium ethylmethacrylate chloride) homopolymer improved squeakiness response for compositions including as surfactant either cocoamidopropyl betaine, sodium laureth sulfate or sodium cocoyl glycinate. Best performance was seen with sodium laureth sulfate as the surfactant. For the latter, improvement in squeakiness ranged between about 54 and 68 grams in relation to a control without homopolymer. For instance, compare control Sample A versus Samples B, C, J and K. Useful, but of lesser effectiveness, was the homopolymer in conjunction with either cocoamidopropyl betaine or sodium cocoyl glycinate.

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

Abstract

La présente invention concerne une composition de nettoyage qui comprend un homopolymère incorporant un monomère qui est un sel de méthacrylate de méthyl et d'ammonium quaternaire de trialkyle, et un détergent synthétique sans savon. La composition présente une valeur de crissement SQ1 dans la plage de 5 à 100 grammes telle que mesurée dans un tribomètre acoustique.
EP13716005.7A 2012-04-30 2013-04-16 Polymères de sels de méthacrylate d'éthyle et d'ammonium quaternaire trialkyle en tant qu'exhausteurs de crissement dans des compositions de nettoyage Withdrawn EP2844349A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB1207443.1A GB201207443D0 (en) 2012-04-30 2012-04-30 Polymers of trialkyl quaternary ammonium methacrylate salts as squeakiness enhancers in cleansing compositions
PCT/EP2013/057871 WO2013164185A1 (fr) 2012-04-30 2013-04-16 Polymères de sels de méthacrylate d'éthyle et d'ammonium quaternaire trialkyle en tant qu'exhausteurs de crissement dans des compositions de nettoyage

Publications (1)

Publication Number Publication Date
EP2844349A1 true EP2844349A1 (fr) 2015-03-11

Family

ID=46330489

Family Applications (1)

Application Number Title Priority Date Filing Date
EP13716005.7A Withdrawn EP2844349A1 (fr) 2012-04-30 2013-04-16 Polymères de sels de méthacrylate d'éthyle et d'ammonium quaternaire trialkyle en tant qu'exhausteurs de crissement dans des compositions de nettoyage

Country Status (7)

Country Link
EP (1) EP2844349A1 (fr)
JP (1) JP2015521168A (fr)
CN (1) CN104411364A (fr)
EA (1) EA027978B1 (fr)
GB (1) GB201207443D0 (fr)
IN (1) IN2014MN02091A (fr)
WO (1) WO2013164185A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023141805A1 (fr) * 2022-01-26 2023-08-03 L'oreal Composition pour le nettoyage et/ou l'élimination de produits de maquillage appliqués sur des matières kératiniques

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU1720897A (en) * 1996-02-15 1997-09-02 Unilever Plc Liquid cleansing compositions comprising select cationic polymers
AU2320197A (en) * 1996-03-27 1997-10-17 Procter & Gamble Company, The Conditioning shampoo compositions
GB0023472D0 (en) * 2000-09-25 2000-11-08 Procter & Gamble Method,apparatus and system for assessing hair condition
ES2260695T3 (es) * 2002-11-12 2006-11-01 Unilever N.V. Composiciones para lavar y acondicionar el cabello.
EP1591102A1 (fr) * 2004-04-30 2005-11-02 The Procter & Gamble Company Procédé et kit pour un conditionnement amélioré des cheveux après teinture, décoloration ou permanente.

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
None *
See also references of WO2013164185A1 *

Also Published As

Publication number Publication date
JP2015521168A (ja) 2015-07-27
GB201207443D0 (en) 2012-06-13
WO2013164185A1 (fr) 2013-11-07
IN2014MN02091A (fr) 2015-10-09
EA027978B1 (ru) 2017-09-29
CN104411364A (zh) 2015-03-11
EA201491768A1 (ru) 2015-04-30

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