Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
  • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
  • C08F220/10—Esters
  • C08F220/12—Esters of monohydric alcohols or phenols
  • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
  • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic 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
  • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
  • A61K8/0241—Containing particulates characterized by their shape and/or structure
• • 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
  • A61K8/044—Suspensions
• • 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
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
  • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
• • 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
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
• • 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
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
  • A61K8/86—Polyethers
• • 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
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
• • 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
  • A61K2800/48—Thickener, Thickening system

Definitions

• the present invention relates to the formulation of stable aqueous compositions comprising suspended particles.
• compositions In addition to the problem raised by the presence of particles, the formulator of acidic aqueous compositions encounters difficulties because the continuous phase of these compositions is not stable and evolves rapidly towards a phase shift. This phenomenon is even more visible when the compositions comprise particles in suspension which may also be entrained in the bottom or on the surface of the container.
• WO 03/061615A discloses cosmetic compositions formulated at a pH of between 6 and 7, used as a hair fixer. They contain a thickener consisting of a polymer known as HASE (hydrophobically modified alkali-swellable) obtained by polymerization of methacrylic acid, of ethyl acrylate, of a hydrophobic monomer constituted by a polymerizable end such as acrylic acid, a mid-ethoxylated portion and a hydrophobic end consisting of a linear hydrocarbon fatty chain and a crosslinking monomer.
• HASE hydrophobically modified alkali-swellable
• the compositions thus formulated have a rheology such that they are sprayable, they do not flow on the hair, while drying quickly once applied.
• compositions comprising a clear continuous phase and suspended particles distributed in the continuous phase, the pH of these compositions being less than 7 and these compositions being stable. It is an important effect that, especially during storage, such compositions, the particles are kept in suspension in the continuous phase, which remains clear. These particles having a technical or only aesthetic function must be able to be visualized and therefore visible at all times.
• a combination of a polymer and a fatty chain has been discovered for the formulation of acidic aqueous compositions in which this combination acts both as a thickener and clarifier of the continuous phase, while allowing a homogeneous distribution of the particles in the continuous phase, said compositions remaining stable over time, and in particular visibly stable.
• the combination of the invention consists of: - a polymer which is obtained from the following monomers: at least one monomer A of acrylic acid and / or methacrylic acid and / or any of their salts,
• At least one monomer B of acrylates and / or alkyl methacrylates At least one monomer B of acrylates and / or alkyl methacrylates
• At least one crosslinking monomer D, and at least one fatty chain C corresponding to the following formula (I):
• RI represents an ethyl, isopropyl and / or sec-butyl radical
• [(EO) n (PO) n (BO) n ] represents a polyalkoxylated chain consisting of alkoxylated units, divided into blocks, alternating or random, chosen from ethoxylated units EO, propoxylated units PO, and butoxylated units B ,
• n, n ', n "representing, independently of each other, 0 or an integer ranging from 1 to 150, the sum of n, n' and n" being not zero, and
• Z represents a fatty chain, linear or branched, of at least 16 carbon atoms.
• the invention relates to an agent for obtaining a stable aqueous composition, comprising a clear continuous phase and particles in suspension distributed in the continuous phase, and having a pH of less than 7, comprising a combination of a polymer resulting from a polymerization of the monomers A, B and D above and a compound C above. It also relates to the aqueous and stable composition thus prepared.
• a composition of the invention may comprise at least one active ingredient (or active agent) or a mixture of active ingredients, in any form whatsoever, and whatever the field of application of the composition, as indicated above.
• the active ingredient (s) may be dissolved in the continuous phase of the composition and / or they may be in particulate form, not soluble in the continuous phase, and constitute all or part of the particles in suspension.
• particles to be suspended to obtain a composition of the invention is meant solid bodies, solid or hollow, liquid or gaseous which can be characterized by shapes, textures, structures, compositions, colors and properties. different endings.
• exfoliating particles for example polyethylene particles, crushed fruit shells, pumice stones
• nourishing particles for example collagen spheres
• pearling particles for example titanium mica
• distearate glycols for example air bubbles, flakes, pigments, possibly colored.
• the particles may have a size of the order of 1, 2 or 3 mm, for example.
• alkyl is meant a linear or branched C m H 2m + 1 group , where m ranges from 1 to 10, or from 1 to 6, or from 1 to 3 or 1 to 2. According to one embodiment, in view of the commercially available monomers, it is a methyl or ethyl group.
• PO propoxylated units and "butoxylated units BO” is meant ethoxylated units bearing on one or other of their carbons, a methyl or ethyl radical respectively.
• An ethoxylated unit is a unit -CH 2 -CH 2 -0.
• fatty chain is meant an aliphatic hydrocarbon chain of a linear or branched fatty acid comprising at least 16 carbon atoms, or from 16 to 36 carbon atoms, or from 16 to 32 carbon atoms.
• the clarity or clarity of a composition is measured by its transmittance.
• a method for determining the transmittance is described below in Example 1, Materials and Methods. It is expressed as a percentage and a The composition is considered clear or clear if it has a transmittance of at least 40%.
• the agent of the invention makes it possible to keep in suspension any particle present in the composition.
• the use of a composition thus formulated therefore requires no mixing step, even if the composition has been stored for several weeks or even several months.
• the agent of the invention is particularly suitable for the preparation of a composition having a pH less than or equal to 5.5, or between 4 and 5. Such pHs are close to the average pH value of human skin , and it thus presents a major interest in cosmetics.
• the agent thus defined preferentially responds to the following characteristics, considered alone or in combination:
• the agent according to the present invention comprises one or more crosslinking monomers D. According to one embodiment, it comprises a single crosslinking monomer. According to another embodiment, it comprises two crosslinking monomers.
• the crosslinking monomer (s) are used to generate a copolymer in the form of a three-dimensional network.
• a monomer which is a polyunsaturated compound.
• This compound may comprise two, three or more ethylenic unsaturations.
• the crosslinking monomer may have a hydrophilic, hydrophobic or amphiphilic character.
• these compounds include di (meth) acrylate compounds such as polyalkylene glycol di (meth) acrylate, especially polypropylene glycol di (meth) acrylate, ethylene glycol di (meth) acrylate, di (meth) polyethylene glycol acrylate, triethylene glycol di (meth) acrylate, 1,3-butylene glycol di (meth) acrylate, 1,6-butylene glycol di (meth) acrylate, di (meth) acrylate, 1,6-hexanediol, neopentyl glycol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, but also 2,2'-bis (4- (acryloxypropyloxyphenyl) propane, 2 , 2'-bis (4- (acryloxydiethoxy-phenyl) propane, and zinc acrylate; tri
• the crosslinking monomers may be prepared by an esterification reaction of a polyol with an unsaturated anhydride such as maleic anhydride, or itaconic anhydride, or by an addition reaction with an isocyanate such as 3-isopropenyl-dimethylbenzene isocyanate.
• an unsaturated anhydride such as maleic anhydride, or itaconic anhydride
• an isocyanate such as 3-isopropenyl-dimethylbenzene isocyanate.
• the following unsaturated compounds which crosslink by means of their pendant carboxyl groups may also be used: polyhaloalkanols such as 1,3-dichloroisopropanol and 1,3-dibromoisopropanol; haloepoxyalkanes such as epichlorohydrin, epibromohydrin, 2-methyl epichlorohydrin, and epiiodohydrin; polyglycidyl ethers such as 1,4-butanediol diglycidyl ether, glycerin-1,3-diglycidyl ether, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, polypropylene glycol diglycidyl ethers, bisphenol A- epichlorohydrin epoxy resins and mixtures.
• polyhaloalkanols such as 1,3-dich
• the proportion of the monomers A, B and D can vary from 11-52, 41-82% and from 0.05-12, respectively, by weight relative to the total weight of the polymer. According to one embodiment, it varies from 31-47, from 51-67% and from 0.5-5, respectively, by weight relative to the total weight of the polymer. Otherwise expressed, the proportion of monomers A, B and D varies from 10-50, 40-80% and 0.05-10, respectively, or 30-40, 50-65% and 0.5- 5, by weight relative to the total weight of the combination polymer / compound C.
• the proportion of the polymer varies from 80-99.9, or from 90-99.5, and that of the compound C varies from 0.1-20, or from 0.5-10, relative to the total weight of the association.
• the polymers are prepared according to methods known to those skilled in the art. More specifically, they are obtained by conventional methods of conventional solution radical copolymerization, by direct or inverse bulk emulsion, by suspension or precipitation in appropriate solvents, in the presence of known initiators and transfer agents, or by controlled radical polymerization processes such as the method called Reversible Addition Fragmentation Transfer (RAFT), the method called Atom Transfer Radical Polymerization (ATRP), the method called Nitroxide Mediated Polymerization (NMP) or the method called Cobaloxime Mediated Free Radical Polymerization.
• RAFT Reversible Addition Fragmentation Transfer
• ATRP Atom Transfer Radical Polymerization
• NMP Nitroxide Mediated Polymerization
• Cobaloxime Mediated Free Radical Polymerization RAFT
• the polymerization is carried out in emulsion.
• the invention also relates to an aqueous cosmetic composition, comprising a continuous phase and particles in suspension in the continuous phase, said continuous phase and / or said particles comprising and / or consisting of a cosmetic active ingredient, and having a pH below 6. or between 4 and 5, said composition comprising an agent as defined above.
• an agent as defined above.
• a principle (s) active (s) it may include a washing base for the body and / or hair.
• the proportion of the agent of the invention may vary from 0.1 to 20, or from 5 to 15, by weight relative to the total weight of the composition.
• the invention also relates to the use for the preparation of a stable aqueous composition, comprising a clear continuous phase and particles in suspension distributed in the continuous phase, and having a pH of less than 7, of a combination of a polymer and a compound C as defined above.
• Example 1 Materials and Methods
• compositions of the invention compared with those of compositions comprising a thickening agent known to those skilled in the art.
• the organoleptic properties of various cosmetic compositions of shower / shampoo type formulated and stored in an oven (45 ° C.) for 3 months are evaluated. The evaluation is performed at room temperature. The following criteria are taken into account: Opacity (change from clear to opaque, even intense white), Texture (smooth, presence of lumps, grains %), Odor (appearance or not of an odor, Color (variation of homogeneity), and Surface (smooth or not smooth).
• the measurement of the clarity is carried out by a measurement of the transmittance which is done in the following way:
• the measurements are carried out on a UV Spectrometer Genesys 10 UV TM (Cole Parmer), equipped with vats Rotilabo-Einmal Kuvetten PS, 4,5 mL. Conveniently, the apparatus is preheated 10 minutes before use.
• a first measurement is made by means of a tank filled with 3.8 ml of bipermuted water (the "white”).
• the measurement is then carried out with a vat filled with 3.8 ml of the cosmetic composition solution to be tested.
• the transmittance is then measured at the wavelength of 500 nm. The higher the transmittance value, expressed in, is higher the more the cosmetic composition is clear.
• Viscoelasticity measurements of different formulations are carried out using a Haake - RheoStress RS 150 rheometer.
• the variation of the phase angle ( ⁇ , in °) as a function of the stress ⁇ (scan of 0 to 800 Pa) is measured at 25 ° C, thanks to the cone-plane module (1 °).
• the limit value of flow (YV, Pa or Dyn / cm) is deduced from these measurements.
• the viscosity of said formulations is measured using a Brookfield viscometer, model RVT. Before measuring the viscosity, each of the formulations is allowed to stand for 24 hours at 25.degree. The mobile must be centered with respect to the opening of the bottle. The viscosity is then measured at 6 rpm (revolutions per minute) using the appropriate module. The viscometer is allowed to rotate until the viscosity is stable.
• EXAMPLE 2 Ultra-Gentle Gumming Shampoo This example illustrates the use of an agent according to the invention in cosmetic formulations of ultra-mild shampoo type, and aims to highlight the rheological properties (suspension and viscosity) and organoleptics brought by this agent.
• the aim was to check in this formula the clarity, the viscosity and the suspension as influenced by different rheology modifiers including those of the prior art and those according to the invention.
• the values mentioned in the last column of the table indicate the masses in grams.
• Protocol for the preparation of the formulation In a beaker, the bipermuted water (1) is introduced, then the various ingredients (2) and (3) are added with stirring.
• the preservative (7) and the perfume (8) are mixed with moderate shaking to the shampoo formulation.
• Table 2 summarizes the set of rheology modifiers that were used as an ingredient (4) in the context of the tests of this example 1. It is noted that their quantity is expressed as a percentage by weight relative to the total weight of the composition. By way of example, if it is equal to 5, 5 g of (4) is added for a formulation of 100 g of finished product. The application results are presented in Tables 2 and 3. State
• Test 1-1 Ingredient (4) is here an inorganic salt: sodium chloride
• Test 1-2 Ingredient (4) is here a crosslinked crosslinked polyacrylate polymer additive, Carbopol® ETD (Lubrizol) Test 1-3: Ingredient (4) is here a crosslinked ASE polymer additive Acrylate ethyl / Acid methacrylic test 1-5: Ingredient (4) is a polymer resulting from the polymerization of monomers A, B, D and monomer C corresponding to the formula T - [(EO) n (PO) n ' (BO) n " ] -Z, in which T represents a methacrylate allowing the copolymerization of the monomer C.

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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)
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• Epidemiology (AREA)
• Birds (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Organic Chemistry (AREA)
• Dispersion Chemistry (AREA)
• Cosmetics (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
• Compositions Of Macromolecular Compounds (AREA)
• Processes Of Treating Macromolecular Substances (AREA)

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• 2012
  • 2012-12-20 FR FR1262416A patent/FR3000086B1/fr not_active Expired - Fee Related
• 2013
  • 2013-12-19 JP JP2015548727A patent/JP2016507495A/ja active Pending
  • 2013-12-19 WO PCT/FR2013/053176 patent/WO2014096710A1/fr active Application Filing
  • 2013-12-19 BR BR112015011480A patent/BR112015011480A2/pt not_active IP Right Cessation
  • 2013-12-19 MX MX2015007805A patent/MX2015007805A/es unknown
  • 2013-12-19 CN CN201380064704.9A patent/CN104837529A/zh active Pending
  • 2013-12-19 KR KR1020157018181A patent/KR20150096693A/ko not_active Application Discontinuation
  • 2013-12-19 EP EP13818356.1A patent/EP2934680A1/fr not_active Withdrawn
  • 2013-12-19 US US14/133,735 patent/US8957008B2/en not_active Expired - Fee Related

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