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    • 专利摘要:
    A self-invertible inverse latex comprising, as an inverter agent, surfactant species of the family of polyglycerol esters, the alkyl chain of which contains from 8 to 18 carbon atoms, associated with polyglycerols comprising from 1 to 10 glycerol units, and their use as a thickening and / or emulsifying and / or stabilizing agent of a topical cosmetic, dermopharmaceutical or pharmaceutical composition, and topical cosmetic, dermopharmaceutical or pharmaceutical compositions comprising it. Surfactant compositions comprising polyglycerol esters having an alkyl chain of 8 to 18 carbon atoms and polyglycerols comprising 1 to 10 glycerol units.
    公开号:FR3079837A1
    申请号:FR1853012
    申请日:2018-04-06
    公开日:2019-10-11
    发明作者:Miruna Bodoc；Georges Dacosta；Jerome Guilbot；Aurelie Pierre
    申请人:Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA；
    IPC主号:
    专利说明:

    The invention relates to self-reversible reverse latexes comprising, as a reversing agent, a surfactant composition comprising polyglycerol esters and glycerol and / or glycerol oligomers, the use of said self-reversible reverse latexes as thickeners used for preparing cosmetic formulations or pharmaceuticals for topical use, as well as said formulations thus prepared. Cosmetic and pharmaceutical compositions for topical use, comprising polar phases such as, for example, aqueous, alcoholic, hydroalcoholic or hydro-glycolic phases, frequently require the use of rheology-modifying polymers to increase the viscosity of said polar phases and more generally for their confer specific rheological behavior. The rheology modifiers provide both an increase in the viscosity of the polar phase, as well as a certain consistency and / or a stabilizing effect of the composition for topical use to be thickened.
    Among the rheology modifying agents which can be used for the preparation of these compositions for topical use, there are synthetic polymers, for example anionic or cationic polyelectrolytes, or ampholytes, linear or branched, crosslinked or noncrosslinked, come in two physical forms, the powder form and the liquid form.
    Said cosmetic and pharmaceutical compositions for topical use are generally in the form of aqueous gels, hydroalcoholic gels, hydro-glycolic gels, emulsions or micro-emulsions or nano-emulsions of the water-in-oil type or of oil-in-water or water-in-oil-in-water or oil-in-water-in-oil type.
    Among the anionic, or cationic, or ampholyte, linear or branched, crosslinked or non-crosslinked polyelectrolytes which are in a liquid form, there are those known under the name of “self-reversible reverse latexes”, which are emulsions of the water- in-oil comprising the polyelectrolyte, an aqueous phase, a fatty phase composed of at least one oil, at least one emulsifier of the water-in-oil type, at least one emulsifier of the oil-in-water type.
    In the processes for preparing self-reversible reverse latexes by carrying out radical polymerization in reverse emulsion, oil-in-water type surfactants are added at the end of the polymerization step. Their addition is intended to modify and regulate the hydrophilic-lipophilic balance of the water-in-oil emulsion comprising the polymer (also called “reverse latex”) so as to obtain a mixture which, once added in a polar phase like for example water, will change direction of emulsion to pass from the water-in-oil form to the oil form
    2018P00095 FR in-water, thus allowing the previously prepared polymer to be brought into contact with the polar phase to be thickened. During such a physical phenomenon, the crosslinked and / or branched polyelectrolyte type polymer deploys in said polar phase and forms a three-dimensional network allowing the polar phase to swell, which is manifested by an increase in the viscosity of this phase. polar. The mixture comprising the “reverse latex” and the oil-in-water type surfactant is called self-reversible reverse latex and said oil-in-water type surfactant is called “reverser” or “reversing agent”.
    The reversing agents commonly used for the preparation of self-reversible reverse latexes are oil-in-water type surfactants which have a HLB (Hydrophilic Lipophilic Balance) value sufficiently high to allow the preparation of oil-type emulsions. stable in-water, generally greater than 9 and less than 16. They generally comprise a hydrophilic part constituted by a chain of ethylene oxide units and a part consisting of an aliphatic hydrocarbon chain of hydrophobic nature. Among these reversing agents are:
    - Ethoxylated fatty alcohols, of which the aliphatic hydrocarbon chain contains from 8 to 14 carbon atoms and of which the number of ethylene oxide units is between 5 and 40, for example lauric ethoxylated alcohol with 7 moles of ethylene oxide (INCI name: Laureth-7), or tridecyl alcohol containing 6 moles of ethylene oxide (INCI name: trideceth-6);
    - The ethoxylated sorbitan esters, the hydrocarbon aliphatic chain of which has 12 to 22 carbon atoms and the number of ethylene oxide units of which is between 5 and 40, for example the ethoxylated sorbitan oleate at 20 moles ethylene oxide sold under the trade name Montanox ™ 80, or sorbitan laurate ethoxylated to 20 moles of ethylene oxide sold under the trade name Montanox ™ 20;
    - Ethoxylated alkylphenols, for example ethoxylated nonylphenols and ethoxylated octylphenols; or
    - Ethoxylated castor oils, for example castor oil ethoxylated with 40 moles of ethylene oxide sold under the brand name SIMULSOL ™ OL 50.
    The evolution of consumer requirements and regulatory provisions lead cosmetic formulators to reduce the proportion of ingredients containing ethylene oxide units in their formulations. There is therefore a need to prepare reverse self-reversible latexes free of ethoxylated surfactants as reversing agents.
    2018P00095 FR
    French patent applications published under the numbers 2 794 034, 2 794 124, 2 808 447, 2 808 446 and 2 810 883 describe the use of alkyl polyglycosides, the alkyl hydrocarbon chain of which has from one to thirty atoms of carbon as reversing agents for preparing reverse self-reversible latexes, such as mixtures of alkyl polyglucosides in which the hydrocarbon alkyl chains are decyl, dodecyl and tetradecyl chains, for example the mixture marketed under the name SIMULSOL ™ SL 10, dodecyl chains, tetradecyl and hexadecyl, for example the mixture marketed under the name SIMULSOL ™ SL 26, octyl and decyl chains, for example the mixture marketed under the name SIMULSOL ™ SL 8, or the undecylenyl chain for example the mixture marketed under the name SIMULSOL ™ SL 11W.
    However, the use of such compounds to prepare self-reversible reverse latexes must be carried out at a temperature above their melting point, generally above 70 ° C., which leads to an increase in the viscosity of the reverse latex. and some destabilization of said prepared self-reversible reverse latex. In some cases, it is made by diluting said alkyl polyglycosides in water beforehand in order to have a liquid form which can be handled at room temperature. This sometimes has the consequence of reducing the speed of inversion of said self-reversible reverse latexes in the polar phases to be thickened, and therefore of decreasing the productivity of the processes for preparing cosmetic formulations comprising such thickening agents.
    The international application published under the number WO 2009/156691 discloses the use of polyglycerol esters as reversing agents for preparing self-reversible reverse latexes, for example decaglycerol esters such as decaglycerol monolaurate, decaglycerol oleate, decaglycerol monocaprylate or decaglycerol monomyristate. However, their use leads to self-reversible reverse latexes for which the rate of inversion in the polar phases to be thickened is too slow and even decreases when the self-reversible reverse latex is stored after its preparation for more than a month. preparation.
    The inventors have therefore sought to develop a new oil-in-water type inverting surfactant system, compatible with the environmental standards in force, by being in particular free of alkylene oxide patterns which make it possible to prepare auto reverse latexes. -invertible:
    - which can be used easily and in particular which can be pumped at 25 ° C, which have a viscosity less than or equal to 8,000 mPa.s, preferably
    2018P00095 FR less than or equal to 5,000 mPa.s, viscosity measured at 25 ° C using a Brookfield RVT viscometer and mobile no.3 at a speed of 20 revolutions / minute,
    - which have a smooth appearance, free from grains or lumps, and
    - which have good reversing properties in polar phases, that is to say inducing a fast and reliable reversing speed.
    The subject of the invention is therefore a self-reversible reverse latex of a crosslinked anionic polyelectrolyte (P) comprising, for 100% molar:
    (ai) - of a proportion greater than or equal to 25 mol% and less than or equal to 80 mol%, of monomeric units derived from 2-methyl acid 2 - [(1-oxo 2-propenyl) amino] 1 -propanesulfonic in free or partially or totally salified acid form;
    (a 2 ) - of a proportion greater than or equal to 20 mol% and less than or equal to 75 mol%, of monomeric units derived from at least one monomer chosen from the elements of the group consisting of acrylamide, Ν , Ν-dimethyl acrylamide; methacrylamide or N-isopropyl acrylamide;
    (a 3 ) - optionally of a proportion greater than 0 mol% and less than or equal to 10 mol%, of monomeric units derived from at least one monomer chosen from the elements of the group consisting of acrylic acid, the methacrylic acid, 2-carboxyethyl acrylic acid, itaconic acid, maleic acid, 3-methyl 3 [(1-oxo 2-propenyl) amino] butanoic acid, the carboxylic function of said monomers being in acid form free, partially salified or fully salified;
    (a 4 ) - of a proportion greater than 0 mol% and less than or equal to 1 mol% of monomeric units derived from at least one diethylenic or polyethylene crosslinking monomer (AR);
    the sum of said molar proportions in monomeric units according to ai), a 2 ) a 3 ) and a 4 ) being equal to 100 mol%;
    said self-reversible reverse latex being a water-in-oil type emulsion (E) comprising for 100% of its mass:
    a) - from 10% by mass to 90% by mass, of said crosslinked anionic polyelectrolyte (P);
    b) - From 5% by mass to 50% by mass, of a fatty phase consisting of at least one oil (H),
    c) - From 1% by mass to 50% by mass of water,
    d) - From 0.5% by mass to 10% by mass of an emulsifier system of the water-oil (Si) type, and
    2018P00095 FR
    e) - From 2% by mass to 10% by mass of an emulsifying system of the oil-in-water type (S 2 );
    the sum of the mass proportions of compounds according to a), b), c), d) and e) being equal to 100% by mass;
    said self-reversible reverse latex being characterized in that said oil-in-water type emulsifying system (S 2 ) comprises for 100% of its mass:
    f) - A proportion greater than or equal to 50% by mass and less than or equal to 100% of a composition (Ce) which comprises for 100% of its mass:
    ei) - From 10% by mass to 60% by mass of at least one compound of formula (I): HO- [CH 2 -CH (OH) -CH 2 -O] n -H (I) in which n represents a whole number greater than or equal to one and less than or equal to fifteen;
    e 2 ) - From 40% by mass to 90% by mass of at least one compound of formula (II)
    Ri- (C = O) - [O-CH 2 -CH (OH) -CH 2 ] P -OH (II), in which p, different or identical to n, represents an integer greater than or equal to one and less or equal to fifteen; and in which the group Ri- (C = O) - represents a saturated or unsaturated, linear or branched aliphatic radical, comprising from six to twenty two carbon atoms, and optionally e 3 ) - Up to 30% by mass of at least a composition (Cn) represented by formula (III):
    HO- [CH 2 -CHOH-CH 2 -O-] q- (G) rH (III), in which q different or identical to n, represents an integer greater than or equal to one and less than or equal to 3, G represents the remainder of a reducing sugar and r represents a decimal number greater than or equal to 1.05 and less than or equal to 5.00, said composition (Cn) consisting of a mixture of the compounds of formulas (llli), (lll 2 ), (lll 3 ), (lll 4 ) and (lll 5 ):
    HO- [CH 2 -CHOH-CH 2 -O-] q -O- (G) iH (III ·),
    HO- [CH 2 -CHOH-CH 2 -O-] q -O- (G) 2 -H (lll 2 ),
    HO- [CH 2 -CHOH-CH 2 -O-] q -O- (G) 3 -H (lll 3 ),
    HO- [CH 2 -CHOH-CH 2 -O-] q -O- (G) 4 -H (lll 4 ),
    HO- [CH 2 -CHOH-CH 2 -O-] q -O- (G) 5 -H (IIls), in molar proportions as said compounds of formulas (III1), (lll 2 ), (lll 3 ) , (lll 4 ) and (1115) respectively equal to ai, a 2 , a 3 , a 4 and as, such that the sum (ai + a 2 + a 3 + a 4 + as) is equal to one, and that the sum (ai + 2a 2 + 3a 3 + 4a 4 + 5as) is equal to r;
    2018P00095 FR the sum of the mass proportions of compounds according to ei), e 2 ) and e 3 ) being equal to 100% by mass.
    Within the meaning of the present invention, by crosslinked anionic polyelectrolyte (P), is meant a nonlinear polyelectrolyte which is in the form of a three-dimensional network insoluble in water, but swellable with water and then leading to l 'obtaining a chemical gel.
    Within the meaning of the present invention, the term “salified” indicates that the acid function present in a monomer is in an anionic form associated in the form of a salt with a cation, in particular the salts of alkali metals, such as sodium cations or potassium, or as the basic nitrogen cations such as the ammonium salt, the lysine salt or the monoethanolamine salt (HOChE-ChE-NHV). These are preferably sodium or ammonium salts.
    According to a particular aspect of the present invention, said self-reversible reverse latex as defined above comprises from 20% by mass to 90% by mass, and more particularly from 30% by mass to 90% by mass, more particularly from 30% by mass to 80% mass, and even more particularly from 33% mass to 80% mass of said crosslinked anionic polyelectrolyte (P).
    According to another particular aspect of the present invention, the molar proportion in monomeric units derived from 2-methyl 2 - [(1-oxo 2-propenyl) amino] 1propanesulfonic acid in free or partially or fully salified acid form present in said crosslinked anionic polyelectrolyte (P) is greater than or equal to 32 mol% and less than or equal to 100 mol%, more particularly greater than or equal to 40 mol% and less than or equal to 100 mol%.
    According to a particular aspect of the present invention, 2-methyl 2 - [(1-oxo 2propenyl) amino] 1-propanesulfonic acid is in the form of sodium or ammonium salt.
    According to a first alternative of the present invention, said crosslinked anionic polyelectrolyte (P) is a copolymer of partially or fully salified 2-methyl 2 - [(1-oxo 2-propenyl) amino] 1- propanesulfonic acid, and d '' at least one monomer chosen from acrylamide, Ν, Ν-dimethyl acrylamide; methacrylamide or N-isopropyl acrylamide.
    According to a second alternative of the present invention, said crosslinked anionic polyelectrolyte (P) is a crosslinked terpolymer of partially or fully salified 2-methyl 2 - [(1-oxo 2propenyl) amino] 1- propanesulfonic acid, of at least at least one monomer chosen from acrylamide, N, N-dimethyl acrylamide; methacrylamide or N-isopropyl acrylamide, and at least one monomer from acrylic acid, acid
    2018P00095 FR methacrylic acid, 2-carboxyethyl acrylic acid, itaconic acid, maleic acid or 3-methyl 3 - [(1-oxo 2-propenyl) amino] butanoic acid, partially salified or fully salified.
    According to another particular aspect of the present invention, said crosslinked anionic polyelectrolyte (P) comes from polymerization, for 100% molar:
    (ai) - of a proportion greater than or equal to 32 mol% and less than 100 mol%, more particularly greater than or equal to 40 mol% and less than or equal to 100 mol%, of monomeric units derived from a monomer having a strong acid function, partially salified or totally salified, more particularly of a sodium salt or an ammonium salt of 2-methyl 2 - [(1-oxo 2-propenyl) amino] 1propanesulfonic acid; and (a 2 ) - of a proportion greater than 0 mol% and less than or equal to 68 mol%, more particularly greater than 0 mol% and less than or equal to 60 mol%, of monomeric units derived from at least one monomer selected from the group consisting of acrylic acid, methacrylic acid, 2carboxyethyl acrylic acid, itaconic acid, maleic acid, 3-methyl 3 - [(1-oxo2propenyl) amino acid ] butanoic, the carboxylic function of said monomers being in acid form, partially salified or totally salified, and / or among the elements of the group consisting of (2-hydroxyethyl acrylate), (2,3-dihydroxy acrylate propyl), (2-hydroxyethyl) methacrylate, (2,3dihydroxypropyl) methacrylate, and vinyl pyrrolidone; and (a 2 ) - of a proportion greater than 0 mol% and less than or equal to 1 mol% of monomeric units derived from at least one diethylene or polyethylene crosslinking monomer (AR); it being understood that the sum of the molar proportions of the monomeric units (ai), (a 2 ) and (as) is equal to 100%.
    By at least one diethylene or polyethylene crosslinking monomer (AR), we denote, in the definition of said crosslinked anionic polyelectrolyte (P), we denote in particular a monomer chosen methylene-bis (acrylamide), ethylene glycol dimethacrylate, diacrylate diethylene glycol, ethylene glycol diacrylate, diallyl urea, triallylamine, trimethylol propanetriacrylate or methylene bis (acrylamide) or a mixture of these compounds, diallyoxyacetic acid or a salt thereof, such as sodium diallyloxyacetate, or a mixture of these compounds; and more particularly a monomer chosen from ethylene glycol dimethacrylate, triallylamine, trimethylol propanetriacrylate or methylenebis (acrylamide) or a mixture of these compounds.
    2018P00095 FR
    According to another particular aspect, said crosslinking monomer (AR) is used in a molar proportion of less than or equal to 0.5%, more particularly less than or equal to 0.25% and very particularly less than or equal to 0.1 %; it is more particularly greater than or equal to 0.005 mol%.
    According to another particular aspect of the present invention, said crosslinked anionic polyelectrolyte (P) is a copolymer crosslinked by triallylamine and / or methylenebis (acrylamide), 2-methyl 2 - [(1-oxo 2-propenyl acid) ) amino] 1-propanesulfonic partially or totally salified in the form of sodium salt or ammonium salt and acrylamide; a copolymer crosslinked with triallylamine and / or methylenebis (acrylamide), 2-methyl 2 - [(1-oxo 2-propenyl) amino] 1-propanesulfonic acid (y) partially or totally salified in the form of salt sodium, and acrylamide (ε), in a molar ratio (γ) / (ε) greater than or equal to 30/70 and less than or equal to 90/10; a copolymer crosslinked with triallylamine and / or methylene-bis (acrylamide), 2-methyl 2 - [(1-oxo 2-propenyl) amino] 1-propanesulfonic acid (γ) partially or totally salified in the form of sodium salt and acrylamide salt (ε) in a molar ratio (γ) / (ε) greater than or equal to 40/60 and less than or equal to 90/10; a terpolymer crosslinked with triallylamine and / or methylene-bis (acrylamide), 2-methyl 2 - [(1oxo 2-propenyl) amino] 1-propanesulfonic acid partially or totally salified in the form of sodium salt or ammonium salt, acrylamide and acrylic acid partially or fully salified in the form of sodium salt or ammonium salt; a terpolymer crosslinked with triallylamine and / or methylene-bis (acrylamide), 2-methyl 2 - [(1-oxo 2-propenyl) amino] 1-propanesulfonic acid partially or totally salified in the form of the sodium salt or ammonium salt in a molar proportion greater than or equal to 30% and less than or equal to 45%, acrylamide in a molar proportion greater than or equal to 45% and less than or equal to 68% and acid partially or totally salified acrylic in the form of sodium salt or ammonium salt in a molar proportion greater than or equal to 2% and less than or equal to 10%, or a terpolymer crosslinked by triallylamine and / or methylene-bis ( acrylamide), 2-methyl 2 - [(1-oxo 2-propenyl) amino] 1propanesulfonic acid partially or totally salified in the form of sodium salt or ammonium salt in a molar proportion greater than or equal to 30% and less than or equal to 45%, of acryla mide in a molar proportion greater than or equal to 47% and less than or equal to 68% and acrylic acid partially or totally salified in the form of sodium salt or ammonium salt in a molar proportion greater than or equal to 2% and less than or equal to 8%.
    2018P00095 FR
    By oil (H) is meant in the definition of said self-reversible reverse latex, in particular:
    - Linear alkanes containing from eleven to nineteen carbon atoms;
    - Branched alkanes, containing from seven to forty carbon atoms, such as isododecane, isopentadecane, isohexadecane, isoheptadecane, isooctadecane, isononadecane or isoeicosane), or mixtures of certain d '' like those listed below and identified by their INCI name: C7-8 isoparaffin, Cs-g isoparaffin, C9.11 isoparaffin, C9-12 isoparaffin, C9-13 isoparaffin, C9-14 isoparaffin, C9-16 isoparaffin , C10.11 isoparaffin, C10-12 isoparaffin, C10-13 isoparaffin, Cn-12 isoparaffin, Cn.13 isoparaffin, Cn-14 isoparaffin, C12-14 isoparaffin, C12-20 isoparaffin, C13-14 isoparaffin, C13-16 isoparaffin ;
    - Cyclo-alkanes optionally substituted by one or more linear or branched alkyl radicals;
    - White mineral oils, such as those sold under the following names: Marcol ™ 52, Marcol ™ 82, Drakeol ™ 6VR, Eolane ™ 130, Eolane ™ 150;
    - Hemisqualane (or 2,6,10-trimethyl-dodecane; CAS number: 3891-98-3), squalane (or 2,6,10,15,19,23-hexamethyltetracosane), hydrogenated polyisobutene or hydrogenated polydecene;
    - Mixtures of alkanes containing from 15 to 19 carbon atoms, said alkanes being linear alkanes, branched alkanes and cyclo-alkanes, and more particularly the mixture (Mi) which comprises, for 100% of its mass, a proportion mass in branched alkanes greater than or equal to 90% and less than or equal to 100%; a mass proportion of linear alkanes greater than or equal to 0% and less than or equal to 9%, and more particularly less than 5% and a mass proportion of cyclo-alkanes greater than or equal to 0% and less than or equal to 1%, by example the mixtures sold under the names Emogreen ™ L15 or Emogreen ™ L19;
    - The fatty alcohol ethers of formula (IV):
    Z1-O-Z2 (IV), in which Z1 and Z 2, which are identical or different, represent a linear or branched alkyl radical containing from five to eighteen carbon atoms, for example dioctyl ether, didecyl ether, didodecyl ether, dodecyl octyl ether, dihexadecyl ether, (1,3-dimethyl butyl) tetradecyl ether, (1,3-dimethyl butyl) hexadecyl ether, bis (1,3-dimethyl butyl) ether or dihexyl ether.
    - Mono-esters of fatty acids and alcohols of formula (V):
    R'i- (C = O) -O-R ' 2 (V),
    2018P00095 FR in which R'i- (C = O) represents an acyl radical, saturated or unsaturated, linear or branched, containing from eight to twenty-four carbon atoms, and R'2 represents, independently of R'i, a saturated or unsaturated, linear or branched hydrocarbon chain having from one to twenty-four carbon atoms, for example methyl laurate, ethyl laurate, propyl laurate, isopropyl laurate, butyl laurate, 2-butyl laurate , hexyl laurate, methyl cocoate, ethyl cocoate, propyl cocoate, isopropyl cocoate, butyl cocoate, 2-butyl cocoate, hexyl cocoate, methyl myristate, ethyl myristate, propyl, isopropyl myristate, butyl myristate, 2-butyl myristate, hexyl myristate, octyl myristate, methyl palmitate, ethyl palmitate, propyl palmitate, palmitate isopropyl, butyl palmitate, 2-buty palmitate , hexyl palmitate, octyl palmitate, methyl oleate, ethyl oleate, propyl oleate, isopropyl oleate, butyl oleate, 2-butyl, hexyl oleate, octyl oleate, methyl stearate, ethyl stearate, propyl stearate, isopropyl stearate, butyl stearate, 2- stearate butyl, hexyl stearate, octyl stearate, methyl isostearate, ethyl isostearate, propyl isostearate, isopropyl isostearate, butyl isostearate, isostearate 2-butyl, hexyl isostearate, isostearyl isostearate;
    - The di-esters of fatty acids and of glycerol of formula (VI) and of formula (VII):
    R'3- (C = O) -O-CH 2 -CH (OH) -CH 2 -O- (C = O) -R'4 (VI)
    R'5- (C = O) -O-CH 2 -CH [O- (C = O) -R ' 6 ] -CH 2 -OH (VII), formulas (VI) (VII) in which R' 3 - (C = O), R ' 4 - (C = O), R' 5 - (C = O), R'e- (C = O), identical or different, represent an acyl group, saturated or unsaturated, linear or branched, having from eight to twenty-four carbon atoms;
    - The tri-esters of fatty acids and glycerol of formula (VIII):
    R'7- (C = O) -O-CH 2 -CH [O- (C = O) -R ” 8 ] -CH 2 -O- (C = O) -R” 9 (VIII), in which R ' - (C = O), R's- (C = O) and R'g- (C = O), identical or different, represent an acyl group, saturated or unsaturated, linear or branched, comprising from eight to twenty-four carbon atoms.
    According to another particular aspect of the present invention, said oil (H) is chosen from undecane, tridecane, isododecane or isohexadecane, mixtures of alkanes and isoalkanes and cycloalkanes such as the mixture (Mi ) as defined above and the mixtures sold under the names Emogreen ™ L15, Emogreen ™ L19, Emosmart ™ L15, Emosmart ™ L19, Emosmart ™ V21, lsopar ™ L or lsopar ™ M; white mineral oils sold under the names Marcol ™ 52, Marcol ™ 82, Drakeol ™ 6VR, Eolane ™ 130 or Eolane ™ 150; the hemisqualane, the
    2018P00095 FR squalane, hydrogenated polyisobutene or hydrogenated polydecene; dioctyl ether or didecyl ether; isopropyl myristate, hexyl palmitate, octyl palmitate, isostearyl isostearate, octanoyl / decanoyl triglyceride, hexadecanoyl / octadecanoyl triglyceride, triglycerides from rapeseed oil, sunflower oil, linseed oil or palm oil.
    In said self-reversible reverse latex which is the subject of the present invention, the water-in-oil type emulsifying system (Si) consists either of a single emulsifying surfactant or of a mixture of emulsifying surfactants, provided that said emulsifying system (Si) resulting has an HLB value low enough to induce the formation of water-in-oil type emulsions.
    As an emulsifying surfactant of the water-in-oil type, there are for example the esters of anhydro hexitol and of aliphatic carboxylic acids, linear or branched, saturated or unsaturated, comprising from 12 to 22 carbon atoms optionally substituted with one or several hydroxyl groups, and more particularly the anhydro hexitol esters chosen from anhydro-sorbitols and anhydro-mannitols and from aliphatic carboxylic acids, linear or branched, saturated or unsaturated, containing from 12 to 22 carbon atoms optionally substituted with one or more hydroxyl groups.
    According to another particular aspect of the present invention, said water-in-oil emulsifier system (Si) is chosen from the elements of the group consisting of sorbitan laurate, for example that marketed under the name Montane ™ 20, palmitate sorbitan, for example that marketed under the name Montane ™ 40, sorbitan stearate, for example that marketed under the name Montane ™ 60, sorbitan oleate, for example that marketed under the name Montane ™ 80, sesquioleate sorbitan, for example that marketed under the name Montane ™ 85, sorbitan trioleate, for example that marketed under the name Montane ™ 83, sorbitan isolaurate, sorbitan isostearate, for example that marketed under the name Montane ™ 70, mannitan laurate, mannitan oleate, or a mixture of these esters; polyesters of molecular weight between 1000 and 3000 and resulting from the condensation between a poly (isobutenyl) succinic acid or its anhydride, such as HYPERMER ™ 2296, or the mixture sold under the brand name SIMALINE ™ IE 501 A, polyglycol polyhydroxystearates of formula (IX):
    (IX),
    2018P00095 FR formula (IX) in which y 3 represents an integer greater than or equal to 2 and less than or equal to 50, Z4 represents the hydrogen atom, the methyl radical, or the ethyl radical, Z 3 represents a radical of formula (X):
    formula (X) in which y'2 represents an integer greater than or equal to 0 and less than or equal to 10, more particularly greater than or equal to 1 and less than or equal to 10 and Z ' 3 represents a radical of formula (X) as defined above, with Z 3 'identical to or different from Z 3 , or the hydrogen atom.
    As an example of an emulsifying surfactant of the water-in-oil type of formula (IX) which can be used to prepare the emulsifying system (Si), there is PEG-30 dipolyhydroxystearate marketed under the name SIMALINE ™ WO, or else mixtures comprising PEG-30 dipolyhydroxystearate and marketed under the names SIMALINE ™ IE 201 A and SIMALINE ™ IE 201 B, or alternatively the mixture comprising Trimethylolpropane-30 tripolyhydroxystearate marketed under the name SIMALINE ™ IE 301 B.
    In said self-reversible reverse latex which is the subject of the present invention, the oil-in-water type emulsifying system (S2) consists either of the single composition (C e ) or of a mixture of said composition (C e ) with one or more other emulsifying surfactants, provided that the resulting emulsifying system (S2) has a HLB value high enough to induce the formation of oil-ineau-type emulsions.
    According to another particular aspect of the present invention, said emulsifier system (S2) of the oil-in-water type comprises for 100% of its mass, at least 75% by mass of said composition (Ce) as defined above.
    According to another particular aspect of the present invention, said composition (Ce) comprises per 100% of its mass:
    ei) - From 15% by mass to 60% by mass, more particularly from 15% by mass to 50% by mass of at least one compound of formula (I) as defined above, e 2 ) - From 40% by mass to 85% by mass , more particularly from 50% by mass to 85% by mass of at least one compound of formula (II) as defined above, and optionally
    2018P00095 FR e 3 ) - From 0% by mass to 25% by mass of at least one composition (Cn) represented by formula (III) as defined above, it being understood that the sum of the mass proportions of the compounds according to (ei), (e 2 ), (e 3 ) is equal to 100%. According to another particular aspect of the present invention, in formula (I) as defined above, n represents an integer greater than or equal to one and less than or equal to ten.
    According to another particular aspect of the present invention, in formula (II) as defined above, p, identical or different to n, represents an integer greater than or equal to one and less than or equal to ten.
    According to another even more particular aspect, n and p are identical and represent an integer greater than or equal to 1 and less than or equal to 10, and even more particularly greater than or equal to 4 and less than or equal to 10.
    According to another particular aspect of the present invention, in formula (II) as defined above, the group Ri- (C = O) - represents a saturated or unsaturated, linear or branched aliphatic radical, comprising from eight to eighteen carbon atoms, and even more particularly the group Ri- (C = O) - is chosen from the elements of the group consisting of the octanoyl, decanoyl, ω-undecylenoyl, dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, 9-octadecenoyl radicals or 9 , 12octadécadiènoyle.
    According to another more particular aspect of the present invention, said self-reversible reverse latex as defined above, is characterized in that in formula (I) as defined above, n represents an integer greater than or equal to one and less than or equal to ten, and in that in formula (II) as defined above, p, identical or different from n, represents an integer greater than or equal to one and less than or equal to ten, and the group Ri- (C = O) - is chosen from the octanoyl, decanoyl, ω-undecylenoyl, dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, 9-octadecenoyl or 9,12-octadecadienoyl radicals.
    According to another even more particular aspect of the present invention, in said formulas (I) and (II) as defined above, n is equal to 10, p is equal to 10, and the group Ri- (C = O) - is the dodecanoyl radical; n is 6, p is 10, and the group Ri- (C = O) - is the dodecanoyl radical; n is equal to 6, p is equal to 6, and the group Ri- (C = O) - is the dodecanoyl radical or n is equal to 1, p is equal to 10, and the group Ri- (C = O) - is the dodecanoyl radical.
    According to another more particular aspect of the present invention, said self-reversible reverse latex as defined above is characterized in that in said
    2018P00095 FR oil-in-water type emulsifier system (S2) said composition (C e ) as defined above, consists of, for 100% of its mass:
    ei) - From 10% by mass to 60% by mass of at least one compound of formula (I) as defined above and e 2 ) - From 40% by mass to 90% by mass of at least one compound of formula (II) as defined above.
    The term “reducing sugar” denotes in formula (III) as defined above, the saccharide derivatives which do not have in their glycosidic binding structures established between an anomeric carbon and the oxygen of an acetal group as defined. in the reference work: Biochemistry, Daniel Voet / Judith G. Voet, p. 250, John Wyley & Sons, 1990. The oligomeric structure (G) x can occur in any form of isomerism, whether it is optical isomerism, geometric isomerism or position isomerism; it can also represent a mixture of isomers.
    According to another more particular aspect of the present invention, in composition (C e ) as defined above, G represents, in formula (III) as defined above, the remainder of a reducing sugar chosen from the remnants of glucose , dextrose, sucrose, fructose, idose, gulose, galactose, maltose, isomaltose, maltotriose, lactose, cellobiose, mannose, ribose, xylose, arabinose, lyxose, allose, altrose, dextran or tallose. Said residue G even more particularly represents in formula (III) as defined above, a reducing sugar chosen from the residues of glucose, xylose and arabinose.
    By the formula (III): HO-CH2- (CHOH) q -CH2-O- (G) r -H, representing the composition (Ci 1), it is meant that this composition (Ou) essentially consists of a mixture of compounds represented by the formulas (III1), (1112), (1113), (1114) and (III5):
    HO-CH 2 - (CHOH) q -CH 2 -O- (G) iH (III1),
    HO-CH 2 - (CHOH) q-CH 2 -O- (G) 2 -H (lll 2 ),
    HO-CH 2 - (CHOH) q-CH 2 -O- (G) 3-H (lll 3 ),
    HO-CH 2 - (CHOH) q-CH 2 -O- (G) 4 -H (lll 4 ),
    HO-CH 2 - (CHOH) q-CH 2 -O- (G) 5 -H (lll 5 ), in the respective molar proportions ai, a2, a 3 , a4 and as, such as the sum 31 + 82 + 33 + 34 + as is equal to 1 and the sum ai + 2a2 + 3a 3 + 4a4 + 5as is equal to r.
    By essentially, it is indicated in the preceding definition, that the presence of one or more compounds of formula (III w ) with w greater than 5 is not excluded
    2018P00095 FR within the composition (Cn), but if there is presence, it is in minimal proportions which do not entail any substantial modification of the properties of the said composition (Cn). In formula (III) as defined above, the HOCH2- (CHOH) q -CH2-O- group is linked to (G) r by the anomeric carbon of the saccharide residue, so as to form an acetal function.
    According to a more particular aspect of the present invention, in the formula (III) representing the composition (Cn) as defined above, r represents a decimal number greater than or equal to 1.05 and less than or equal to 3, more particularly greater than or equal to 1.15 and less than or equal to 2.5.
    According to a more particular aspect of the present invention, said self-reversible reverse latex as defined above is characterized in that in formula (III) as defined above, q is equal to one, G represents the remainder of the glucose and r represents a decimal number greater than or equal to 1.05 and less than or equal to 2.5.
    According to another particular aspect of the present invention, said self-reversible reverse latex as defined above is characterized in that in said oil-in-water type emulsifier system (S2), said composition (C e ) as defined above consists of , for 100% of its mass:
    ei) - From 5% by mass to 15% by mass of at least one compound of formula (I) as defined above, e 2 ) - From 60% by mass to 80% by mass of at least one compound of formula (II) as defined above, and e 3 ) - From 5% to 15% by mass of at least one composition (Cn) represented by the formula (III) as defined above.
    According to a very particular aspect, said reverse latex as defined above is characterized in that said emulsifying system of the oil-in-water type (S2) is said composition (C e ) as defined above.
    According to a very particular aspect, said self-reversible reverse latex as defined above, is characterized in that said emulsifying system of oil-in-water type (S2) is said composition (C e ).
    According to an even more particular aspect of the present invention, in the composition (Ce) as defined above:
    - n represents an integer greater than or equal to one and less than or equal to ten in formula (I) as defined above, and
    - p, identical or different from n, represents an integer greater than or equal to one and less than or equal to ten in formula (II) as defined above,
    2018P00095 FR
    - the group Ri- (C = O) - is chosen from the elements of the group consisting of the octanoyl, decanoyl, ω-undecylenoyl, dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, 9-octadecenoyl or 9,12-octadecadienoyl radicals, and
    - q is equal to one, G represents the remainder of the glucose and r represents a decimal number greater than or equal to 1.05 and less than or equal to 2.5, in the formula (III) as defined above.
    Said self-reversible reverse latex which is the subject of the present invention is prepared by the implementation of a process known as “reverse emulsion polymerization”, well known to those skilled in the art, and which comprises the following steps:
    - A step a) of preparation of an aqueous phase comprising water, the water-soluble monomers and optionally the crosslinking monomer (AR), as well as additives commonly used such as, for example, sequestering agents such as ethylenediaminetetracetic (EDTA) in its sodium form, or the pentasodium salt of penta acetic acid of diethylenetramine (sold under the brand name Versenex ™ 80);
    - A step b) of mixing the oily phase (H) with the water-in-oil type emulsifier system (Si);
    - A step c) of mixing the aqueous phase and the oily phase, prepared during the previous steps, and emulsification using a rotor-stator type mobile;
    - A step d) of nitrogen inerting;
    - A step e) of initiating the polymerization reaction by introduction into the emulsion formed in c), of a free radical initiator and possibly a coinitiator; then we let it unfold,
    - A step f) of introducing the emulsifier system (S 2 ) of the oil-in-water type as defined above at a temperature less than or equal to 50 ° C.
    According to a particular aspect of the process as defined above, the polymerization reaction of step e) is initiated by an oxidation-reduction couple generating hydrogen sulfite ions (HSCbj, such as the cumene hydroperoxide couple of sodium metabisulfite (Na 2 S 2 0s) or the cumene hydroperoxide-thionyl chloride couple (SOCI 2 ) at a temperature less than or equal to 10 ° C., if desired accompanied by a polymerization co-initiating agent such as for example azo-bis (isobutyronitrile) then carried out either in an almost adiabatic manner up to a temperature greater than or equal to 50 ° C., or by controlling the temperature.
    2018P00095 FR
    According to another particular aspect of the process as defined above, the reaction medium from step e) is concentrated by distillation, before the implementation of step f).
    According to another particular aspect of the process as defined above, the reaction medium resulting from step e) or from step f) undergoes a spray drying step in a suitable installation.
    According to another particular aspect of the process as defined above, the aqueous phase prepared in step a) can comprise chain reducing agents, intended to reduce the length of the polymer chains formed and to increase the rate of connection to the polymer, so as to modify the rheological properties.
    Among the chain reducing agents suitable for the process as defined above, there are methanol, isopropanol, butylene glycol, 2-mercapto ethanol, thioglycolic acid, formic acid or its salts.
    The subject of the invention is also the use of said self-reversible reverse latex as defined above, as a thickening and / or emulsifying and / or stabilizing agent of a topical cosmetic or pharmaceutical composition.
    According to a particular aspect, said use consists in thickening polar phases such as for example the aqueous, alcoholic or hydro-alcoholic phases or the polar phases comprising polyols such as glycerol.
    According to another particular aspect, said use consists in stabilizing an emulsion of oil-in-water type, or of water-in-oil type, by imparting a homogeneous appearance to said emulsion during storage under different conditions, and more particularly at 25. ° C for a duration at least equal to one month, and more particularly at 4 ° C for a duration at least equal to one month, and more particularly at 45 ° C for a duration at least equal to one month.
    According to another particular aspect, said use consists in stabilizing solid particles in topical cosmetic, dermopharmaceutical or pharmaceutical compositions. These solid particles to be suspended can have different geometries, regular or irregular, and be in the form of pearls, beads, rods, flakes, lamellae or polyhedra. These solid particles are characterized by an apparent average diameter of between one micrometer and five millimeters, more particularly between ten micrometers and one millimeter.
    Among the solid particles which can be suspended and stabilized by the self-reversible reverse latex as defined above in topical cosmetic, dermopharmaceutical or pharmaceutical compositions, there are micas, iron oxide, titanium oxide. , zinc oxide, aluminum oxide, talc,
    2018P00095 FR silica, kaolin, clays, boron nitride, calcium carbonate, magnesium carbonate, magnesium hydrogen carbonate, inorganic color pigments, polyamides such as nylon-6, polyethylenes, polypropylenes , polystyrenes, polyesters, acrylic or methacrylic polymers such as polymethylmethacrylates, polytetrafluoroethylene, crystalline or microcrystalline waxes, porous spheres, selenium sulphide, zinc pyrithione, starches, alginates, plant fibers, particles of Loofah, particles of sponges.
    The subject of the invention is also a topical cosmetic composition (F) or a topical pharmaceutical composition (G), characterized in that it comprises, as thickening agent, for 100% of its total mass between 0.1% and 10% by mass of said self-reversible reverse latex as defined above.
    The topical expression used in the definitions of said compositions (F) and (G), means that they are applied by application to the skin, hair, scalp or mucous membranes, whether '' a direct application in the case of a cosmetic, dermocosmetic, dermopharmaceutical or pharmaceutical preparation or an indirect application for example in the case of a body care product in the form of a textile or paper wipe or sanitary products intended to be in contact with the skin or mucous membranes.
    Said compositions (F) and (G) are generally in the form of an aqueous or hydro-alcoholic or hydro-glycolic solution, in the form of a suspension, an emulsion, a microemulsion or a nano -emulsion, whether of water-in-oil, oil-in-water, water-in-oil-in-water or oil-in-water-in-oil type.
    Said compositions (F) and (G), can be packaged in a bottle, in a device of the pump bottle type, in pressurized form in an aerosol device, in a device provided with an openwork wall such as a grid or in a device provided a ball applicator (called roll-on).
    In general, said compositions (F) and (G) also comprise excipients and or active ingredients usually used in the field of formulations for topical use, in particular cosmetic, dermocosmetic, pharmaceutical or dermopharmaceuticals, such as thickening surfactants and / or gelling agents, stabilizers, film-forming compounds, hydrotropic agents, plasticizing agents, emulsifying and co-emulsifying agents, opacifying agents, pearlescent agents, superfatting agents, sequestrants, chelating agents, antioxidants, perfumes, preservatives, conditioning agents,
    2018P00095 FR whitening agents intended for bleaching hair and skin, active ingredients intended to provide a treatment action with respect to the skin or hair, sun filters, mineral fillers or pigments, particles providing a visual effect or intended for the encapsulation of active ingredients, exfoliating particles, texture agents.
    As examples of foaming and / or detergent surfactants which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are cationic foaming surfactants and / or anionic detergents. , amphoteric or non-ionic.
    Among the anionic foaming and / or detergent surfactants which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are the salts of alkali metals, alkali metal- earthy, ammonium, amines, or amino alcohols of alkyl ether sulfates, alkyl sulfates, alkylamidoether sulfates, alkylaryl polyethersulfates, monoglycerides sulfates, alpha olefins sulfonates, paraffins sulfonates, alkyl phosphates , alkyl ether phosphates, alkyl sulfonates, alkylamide sulfonates, alkylaryl sulfonates, alkyl carboxylates, alkyl sulfosuccinates, alkyl ether sulfosuccinates, alkylamide sulfosuccinates, alkyl sulfoacetates, alkyl sarcosinates , acyl isethionates, N-acyl taurates, acyl lactylates, N-acylated derivatives of amino acids, N-acylated derivatives of peptides, N-acylated derivatives of proteins, N-acylated derivatives of acid are bold.
    Among the foaming amphoteric surfactants and / or detergents which can be associated with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are alkylbetaines, alkylamidobetaines, sultaines, alkylamidoalkylsulfobetaines, imidazoline derivatives, phosphobetaines, amphopolyacetates and amphopropionates.
    Among the foaming cationic surfactants and / or detergents which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are in particular quaternary ammonium derivatives.
    Among the foaming nonionic surfactants and / or detergents which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are more particularly alkylpolyglycosides comprising an aliphatic radical, linear or branched, saturated or unsaturated, and having from 8 to 16 carbon atoms, such as octyl polyglucoside, decyl polyglucoside, undecylenyl polyglucoside, dodecyl polyglucoside, tetradecyl polyglucoside, hexadecyl polyglucoside, 1-12 dodecanediyl polyglucoside; ethoxylated hydrogenated castor oil derivatives such as the product sold under the name INCI "Peg-40
    2018P00095 FR hydrogenated castor oil ”; polysorbates such as Polysorbate 20, Polysorbate 40, Polysorbate 60, Polysorbate 70, Polysorbate 80, Polysorbate 85; copra amides; N-alkylamines.
    As examples of thickening and / or gelling surfactants which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are fatty esters of optionally alkoxylated alkylpolyglycosides, such as ethoxylated methylpolyglucoside esters such as PEG 120 methyl glucose trioleate and PEG 120 methyl glucose dioleate sold respectively under the names GLUCAMATE ™ LT and GLUMATE ™ DOE120; alkoxylated fatty esters such as PEG 150 pentaerythrytyl tetrastearate marketed under the name CROTHIX ™ DS53, PEG 55 propylene glycol oleate marketed under the name ANTIL ™ 141; fatty chain polyalkylene glycol carbamates such as PPG-14 laureth isophoryl dicarbamate sold under the name ELFACOS ™ T211, PPG-14 palmeth-60 hexyl dicarbamate sold under the name ELFACOS ™ GT2125.
    As examples of thickening and / or gelling agents which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are the copolymers of AMPS and of alkyl acrylates, the carbon chain of which comprises between four and thirty carbon atoms and more particularly between ten and thirty carbon atoms, the linear, branched or crosslinked terpolymer of at least one monomer having a strong, free, partially salified acid function or totally salified, with at least one neutral monomer, and at least one monomer of formula (XIII):
    CH2 = C (R'3) -C (= O) - [CH2-CH 2 -O] n'-R'4 (XIII) in which R'3 represents a hydrogen atom or a methyl radical, R ' 4 represents a linear or branched alkyl radical containing from eight to thirty carbon atoms and n 'represents a number greater than or equal to one and less than or equal to fifty.
    As examples of thickening and / or gelling agents which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are the polysaccharides consisting solely of oses, such as glucans or homopolymers of glucose, glucomannoglucans, xyloglycans, galactomannans whose degree of substitution (DS) of D-galactose units on the main chain of D-mannose is between 0 and 1, and more particularly between 1 and 0.25, such as galactomannans from cassia gum (DS =
    2018P00095 FR
    1/5), locust bean gum (DS = 1/4), tara gum (DS = 1/3), guar gum (DS = 1/2), fenugreek gum ( DS = 1).
    As examples of thickening and / or gelling agents which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are the polysaccharides consisting of derivatives of oses, such as sulfated galactans and more particularly carrageenans and agar, uronanes and more particularly algines, alginates and pectins, heteropolymers of oses and uronic acids and more particularly xanthan gum, gellan gum, exudate of arabic gum and karaya gum, glucosaminoglycans.
    As examples of thickening and / or gelling agents which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there is cellulose, cellulose derivatives such as methylcellulose, ethylcellulose, hydroxypropylcellulose, silicates, starch, hydrophilic starch derivatives, polyurethanes.
    As examples of stabilizing agents which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are microcrystalline waxes, and more particularly ozokerite, the salts minerals such as sodium chloride or magnesium chloride, silicone polymers such as polysiloxane polyalkyl polyether copolymers.
    As examples of solvents which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are water, organic solvents such as glycerol, diglycerol, oligomers of glycerol, ethylene glycol, propylene glycol, butylene glycol, 1,3-propanediol, 1,2propanediol, hexylene glycol, diethylene glycol, xylitol, erythritol, sorbitol, water-soluble alcohols such as l ethanol, isopropanol or butanol, mixtures of water and said organic solvents.
    As examples of thermal or mineral waters which can be associated with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are thermal or mineral waters having at least mineralization. minus 300 mg / l, in particular Avene water, Vittel water, Vichy basin water, Uriage water, Roche Posay water, Bourboule water, water from Enghien-les-bains, water from Saint-Gervais-les bains, water from Néris-les-bains, water from Allevard-les-bains, water from Digne, l water from Maizieres, water from Neyrac-les-bains, water from Lons le Saunier, water from Rochefort, water from Saint Christau, water from Fumades and water from Tercis-les- baths.
    2018P00095 FR
    As examples of hydrotropic agents which can be combined with said self-reversible reverse latex as defined above, in said compositions (F) and (G), there are the xylenes sulfonates, the cumenes sulfonates, the hexylpolyglucoside, 2ethylhexylpolyglucoside, n-heptylpolyglucoside.
    As examples of emulsifying surfactants which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are nonionic surfactants, anionic surfactants, cationic surfactants .
    As examples of nonionic emulsifying surfactants which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are the esters of fatty acids and of sorbitol, such as the products sold under the names MONTANE ™ 40, MONTANE ™ 60, MONTANE ™ 70, MONTANE ™ 80 and MONTANE ™ 85; compositions comprising glycerol stearate and ethoxylated stearic acid between 5 moles and 150 moles of ethylene oxide, such as the composition comprising ethoxylated stearic acid with 135 moles of ethylene oxide and glycerol stearate sold under the name SIMULSOL ™ 165; mannitan esters; ethoxylated mannitan esters; sucrose esters; methylglucoside esters; alkylpolyglycosides comprising an aliphatic radical, linear or branched, saturated or unsaturated, and comprising from 14 to 36 carbon atoms, such as tetradecyl polyglucoside, hexadecyl polyglucoside, octadecyl polyglucoside, hexadecyl polyxyloside, octadecyl polyxyloside, eicosyl polyglucoside, dodecosyl polyglucoside, 2-octyldodecyl polyxyloside, 12-hydroxystearyl polyglucoside; the compositions of linear or branched fatty alcohols, saturated or unsaturated, and comprising from 14 to 36 carbon atoms, and of alkylpolyglycosides as described above, for example the compositions sold under the names MONTANOV ™ 68, MONTANOV ™ 14, MONTANOV ™ 82, MONTANOV ™ 202, MONTANOV ™ S, MONTANOV ™ WO18, MONTANOV ™ L, FLUIDANOV ™ 20X and EASYNOV ™.
    As examples of anionic surfactants which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are glyceryl stearate citrate, cetearyl sulphate, soaps such as stearate sodium or triethanolammonium stearate, N-acylated derivatives of salified amino acids, for example stearoyl glutamate.
    As examples of cationic emulsifying surfactants which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are the aminoxides, quaternium-82 and the surfactants described
    2018P00095 FR in the international application published under the number WO 96/00719 and mainly those in which the fatty chain comprises at least 16 carbon atoms.
    As examples of opacifying and / or pearlescent agents which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are sodium palmitate, sodium stearate. , sodium hydroxystearate, magnesium palmitate, magnesium stearate, magnesium hydroxystearate, ethylene glycol monostearate, ethylene glycol distearate, polyethylene glycol monostearate, polyethylene glycol distearate, fatty alcohols having from 12 to 22 carbon atoms.
    As examples of texturing agents which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are N-acylated derivatives of amino acids, such as lauroyl lysine marketed under the name AMINOHOPE ™ LL, octenyl starch succinate marketed under the name DRYFLO ™, myristyl polyglucoside marketed under the name MONTANOV ™ 14, cellulose fibers, cotton fibers, chitosan fibers , talc, sericite or mica.
    As examples of deodorant agents which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are alkali silicates, zinc salts such as zinc sulfate , zinc gluconate, zinc chloride, zinc lactate; quaternary ammonium salts such as cetyltrimethylammonium salts, cetylpyridinium salts; glycerol derivatives such as glycerol caprate, glycerol caprylate, polyglycerol caprate; 1,2 decanediol; 1,3 propanediol; salicylic acid; sodium bicarbonate; cyclodextrins; metallic zeolites; TRICLOSAN ™; aluminum hydrobromide, aluminum hydrochlorides, aluminum chloride, aluminum sulfate, aluminum and zirconium hydrochlorides, tri aluminum and zirconium hydrochloride, aluminum and tetrachlorhydrate zirconium, aluminum and zirconium pentachlorhydrate, aluminum and zirconium octochlorhydrate, aluminum sulfate, sodium and aluminum lactate, complexes of aluminum hydrochloride and glycol, such as the complex aluminum hydrochloride and propylene glycol, aluminum dihydrochloride and propylene glycol complex, aluminum sesquichlorohydrate and propylene glycol complex, aluminum hydrochloride and polyethylene glycol complex, dihydrochloride complex aluminum and polyethylene glycol, the complex of aluminum sesquichlorohydrate and polyethylene glycol.
    2018P00095 FR
    As examples of oils which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are mineral oils such as paraffin oil, petrolatum oil , isoparaffins or white mineral oils; oils of animal origin, such as squalene or squalane; vegetable oils, such as phytosqualane, sweet almond oil, coconut oil, castor oil, jojoba oil, olive oil, rapeseed oil, peanut oil, sunflower oil, wheat germ oil, corn germ oil, soybean oil, cottonseed oil, alfalfa oil, poppy oil , pumpkin oil, evening primrose oil, millet oil, barley oil, rye oil, safflower oil, bancoulier oil, passionflower oil , hazelnut oil, palm oil, shea butter, apricot kernel oil, calophyllum oil, sysymbrium oil, avocado oil, calendula, oils from flowers or vegetables ethoxylated vegetable oils; synthetic oils such as fatty acid esters such as butyl myristate, propyl myristate, isopropyl myristate, cetyl myristate, isopropyl palmitate, octyl palmitate, butyl stearate, hexadecyl stearate, isopropyl stearate, octyl stearate, isocetyl stearate, dodecyl oleate, hexyl laurate, propylene glycol dicaprylate, esters derived from lanolic acid, such as isopropyl lanolate, isocetyl lanolate, monoglycerides, diglycerides and triglycerides of fatty acids such as glycerol triheptanoate, alkylbenzoates, hydrogenated oils, poly (alpha-olefins), polyolefins such as poly (isobutane ), synthetic isoalkanes such as isohexadecane, isododecane, perfluorinated oils; silicone oils such as dimethylpolysiloxanes, methylphenylpolysiloxanes, silicones modified by amines, silicones modified by fatty acids, silicones modified by alcohols, silicones modified by alcohols and fatty acids, silicones modified by polyether groups, modified epoxy silicones, silicones modified by fluorinated groups, cyclic silicones and silicones modified by alkyl groups. By "oils" is meant in the present application the compounds and / or mixtures of compounds insoluble in water, having a liquid appearance at a temperature of 25 ° C.
    As examples of waxes which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are beeswax, carnauba wax, candelilla wax, ouricoury wax, Japanese wax, cork fiber wax, sugar cane wax, paraffin waxes, lignite waxes, microcrystalline waxes, lanolin wax; ozokerite; polyethylene wax; silicone waxes; vegetable waxes; fatty alcohols and solid fatty acids
    2018P00095 FR at room temperature; solid glycerides at room temperature. By "waxes" is meant in the present application the compounds and / or mixtures of compounds insoluble in water, having a solid appearance at a temperature greater than or equal to 45 ° C.
    As examples of active principles which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are vitamins and their derivatives, in particular their esters, such as retinol. (vitamin A) and its esters (retinyl palmitate for example), ascorbic acid (vitamin C) and its esters, sugar derivatives of ascorbic acid (like ascorbyl glucoside), tocopherol (vitamin E) and its esters (such as tocopherol acetate), vitamins B3 or B10 (niacinamide and its derivatives); compounds showing a lightening or depigmenting action on the skin such as ω-undecelynoyl phenylalanine sold under the name SEPIWHITE ™ MSH, SEPICALM ™ VG, the mono ester and / or glycerol diester of ω-undecelynoyl phenylalanine, ω- undecelynoyl dipeptides, arbutin, kojic acid, hydroquinone; compounds showing a soothing action, in particular SEPICALM ™ S, allantoin and bisabolol; anti-inflammatory agents; compounds showing a hydrating action such as urea, hydroxyureas, glycerol, polyglycerols, glycerolglucoside, diglycerolglucoside, polyglycerylglucosides, xylitylplucoside; plant extracts rich in polyphenols such as grape extracts, pine extracts, wine extracts, olive extracts; compounds showing a slimming or lipolytic action such as caffeine or its derivatives, ADIPOSLIM ™, ADIPOLESS ™, fucoxanthin; N-acylated proteins; N-acylated peptides such as MATRIXIL ™; N-acylated amino acids; partial hydrolysates of N-acylated proteins; amino acids; peptides; total protein hydrolysates; soy extracts, for example Raffermine ™; wheat extracts, for example TENSINE ™ or GLIADINE ™; plant extracts, such as plant extracts rich in tannins, plant extracts rich in isoflavones or plant extracts rich in terpenes; extracts of freshwater or marine algae; extracts of marine plants; marine extracts in general such as corals; essential waxes; bacterial extracts; ceramides; phospholipids; compounds showing an antimicrobial action or a purifying action, such as LIPACIDE ™ C8G, LIPACIDE ™ UG, SEPICONTROL ™ A5; OCTOPIROX ™ or SENSIVA ™ SC50; compounds showing an energizing or stimulating property such as PHYSIOGENYL ™, panthenol and its derivatives such as SEPICAP ™ MP; anti-aging active ingredients such as SEPILIFT ™ DPHP, LIPACIDE ™ PVB, SEPIVINOL ™, SEPIVITAL ™, MANOLIVA ™, PHYTO
    2018P00095 FR
    AGE ™, TIMECODE ™; SURVICODE ™; anti-photo aging active ingredients; protective agents for the integrity of the dermo-epidermal junction; active ingredients increasing the synthesis of components of the extracellular matrix such as collagen, elastins, glycosaminoglycans; active agents favorably acting on chemical cellular communication such as cytokines or physical ones such as integrins; active ingredients creating a feeling of "warming" on the skin such as activators of the microcirculation of the skin (such as nicotinic acid derivatives) or products creating a feeling of "freshness" on the skin (such as menthol and derivatives) ; active ingredients improving skin microcirculation, for example veinotonics; draining active ingredients; decongestant active ingredients such as extracts of ginko biloba, ivy, horse chestnut, bamboo, ruscus, small holly, centalla asiatica, fucus, rosemary, willow; agents for tanning or browning the skin, for example dihydroxyacetone (DHA), erythrulose, mesotartaric aldehyde, glutaraldehyde, glyceraldehyde, alloxane, ninhydrin, plant extracts for example wood extracts reds of the genus Pterocarpus and of the genus Baphia such as Pteropcarpus santalinus, Pterocarpus osun, Pterocarpus soyauxii, Pterocarpus erinaceus, Pterocarpus indicus or Baphia nitida as those described in European patent application EP 0 971 683; agents known for their facilitating and / or accelerating action on the tanning and / or browning of human skin, and / or for their coloring action on human skin, for example caratenoids such as beta carotene and gamma carotene, the product marketed under the brand name "Garrot oil" (INCI name: Daucus Carota, helianthus annuus Sunflower oil) by the company Provital, which contains carotenoids, vitamin E and vitamin K; tyrosine and / or its derivatives, known for their effect on the acceleration of tanning of human skin in association with exposure to ultraviolet radiation, for example the product marketed under the brand name "SunTan Accelerator ™" by the Provital which contains tyrosine and riboflavins (vitamin B), the tyrosine and tyrosinase complex marketed under the brand name "Zymo Tan Complex" by the company Zymo Line, the product marketed under the brand name MelanoBronze ™ ( INCI name: Acetyl Tyrosine, Monk's pepper extract (Vitex Agnus-castus)) by the company Mibelle which contains acetyl tyrosine, product marketed under the brand name Unipertan VEG-24/242/2002 (INCI name: butylene glycol and Acetyl Tyrosine and hydrolyzed vegetable protein and Adenosine triphosphate) by the company UNIPEX, the product marketed under the brand name "Try-Excell ™" (INCI name: Oleoyl Tyrosine and Luffa Cylind rica (Seed) Oil and Oleic acid) by the company Sederma which contains extracts of pumpkin seeds (or
    2018P00095 FR Loofah oil), the product marketed under the brand name "Actibronze ™" (INCI name: hydrolyzed wheat protein and acetyl tyrosine and copper gluconate) by the company Alban Muller, the product marketed under the brand name Tyrostan ™ ( INCI name: potassium caproyl tyrosine) by the company Synerga, the product marketed under the brand name Tyrosinol (INCI name: Sorbitan Isostearate, glyceryl oleate, caproyl Tyrosine) by the company Synerga, the product marketed under the brand name InstaBronze ™ ( INCI name: Dihydroxyacetone and acetyl tyrosine and copper gluconate) marketed by the company Alban Muller, the product sold under the brand name Tyrosilane (INCI name: methylsilanol and acetyl tyrosine) by the company Exymol; peptides known for their melanogenesis activation effect, for example the product marketed under the brand name Bronzing SF Peptide powder (INCI name: Dextran and Octapeptide-5) by the company Infinitec Activos, the product marketed under the brand name Melitane (INCI name: Glycerin and Aqua and Dextran and Acetyl hexapeptide1) comprising acetyl hexapeptide-1 known for its agonist action of alpha-MSH, the product marketed under the brand name Melatimes Solutions ™ (INCI name: Butylene glycol ,
    Palmitoyl Tripeptide-40) by the company LIPOTEC, sugars and sugar derivatives, for example the product marketed under the brand name Tanositol ™ (INCI name: inositol) by the company Provital, the product marketed under the brand name Thalitan ™ (or Phycosaccharide ™ AG) by the company CODIF international (INCI name: Aqua and Hydrolyzed algin (Laminaria Digitata) and magnesium sulfate and manganese sulfate) containing an oligosaccharide of marine origin (guluronic acid and mannuronic acid chelated with magnesium and manganese ions ), the product marketed under the brand name Melactiva ™ (INCI name: Maltodextrin, Mucuna Pruriens Seed extract) by the company Alban Muller, compounds rich in flavonoids for example the product marketed under the brand name "Biotanning" (INCI name : Hydrolyzed citrus Aurantium dulcis fruit extract) by the company Silab and known to be rich in lemon flavonoids (hesperidin type es); agents intended for the treatment of hair and / or body hair, for example agents protecting the hair follicle melanocytes, intended to protect said melanocytes against the cytotoxic agents responsible for senescence and / or apoptosis of said melanocytes, such as agents mimicking the activity of DOPAchrome tautomerase chosen from those described in the European patent application published under the number EP1 515 688, synthetic molecules mimicking SOD, for example manganese complexes, antioxidant compounds, for example derivatives of cyclodextrin, siliceous compounds derived from ascorbic acid, lysine pyrrolidone carboxylate or
    2018P00095 FR of arginine, combinations of mono- and diester of cinnamic acid and vitamin C, and more generally those cited in the aforementioned European patent application.
    As examples of antioxidant agents which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there is EDTA and its salts, citric acid, l tartaric acid, oxalic acid, BHA (butylhydroxyanisol), BHT (butylhydroxytoluene), tocopherol derivatives such as tocopherol acetate, mixtures of antioxidant compounds such as DISSOLVINE ™ GL 47S marketed by the company Akzo Nobel under the name INCI: Tetrasodium Glutamate Diacetate.
    As examples of sunscreens which can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are all those appearing in cosmetic directive 76/768 / EEC as amended annex. VII.
    Among the organic sunscreens that can be combined with said self-reversible reverse latex as defined above in said compositions (F) and (G), there is the family of benzoic acid derivatives such as para- acids. aminobenzoic acid (PABA), in particular the monoglycerol esters of PABA, the ethyl esters of N, N25 propoxy PABA, the ethyl esters of Ν, Ν-diethoxy PABA, the ethyl esters of N. Ndimethyl PABA, the methyl esters of Ν, Ν -dimethyl PABA, the butyl esters of N.Ndimethyl PABA; the family of anthranilic acid derivatives such as homomenthyl-N-acetyl anthranilate; the family of salicylic acid derivatives such as amyl salicylate, homomenthyl salicylate, ethylhexyl salicylate, phenyl salicylate, benzyl salicylate, p-isopropanolphenyl salicylate; the family of cinnamic acid derivatives such as ethylhexyl cinnamate, ethyl-4-isopropyl cinnamate, methyl 2,5-diisopropyl cinnamate, p-methoxypropyl cinnamate, p-methoxyisopropyl cinnamate , pmethoxyisoamyl cinnamate, p-methoxyoctyl cinnamate (pmethoxy 2ethylhexyl cinnamate), p-methoxy 2-ethoxyethyl cinnamate, methoxycyclohexyl p-cinnamate, ethyl-a-cyano-p-phenyl cinnamate , 2ethylhexyl-a-cyano-p-phenyl cinnamate, glyceryl diparamethoxy mono-2-ethylhexanoyl cinnamate; the family of benzophenone derivatives such as 2,4dihydroxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2 ', 4,4'tétrahydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy -4methoxy-4'-methylbenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 4-phenylbenzophenone, 2-ethylhexyl-4'-phenylbenzophenone-2-5 carboxylate, 2-hydroxy-4-n- octyloxy benzophenone, 4-hydroxy-3-carboxy benzophenone; 3- (4'methylbenzylidene) -d, l-camphor, 3 (benzylidene) -d, lcamphre, benzalkonium
    2018P00095 FR camphor methosulfate; urocanic acid, ethyl urocanate; the family of sulfonic acid derivatives such as 2-phenylbenzimidazole-5 sulfonic acid and its salts; the family of triazine derivatives such as hydroxyphenyl triazine, ethylhexyloxyhydroxyphenyl-4-methoxyphenyltriazine, 2,4,6-trianillino- (p-carbo-2'ethylhexyl-T-oxy) -1,3,5- triazine, 4,4 - ((6 - (((1,1-dimethylethyl) amino) carbonyl) phenyl) amino) -1,3,5-triazine-2,4-diyl diimino) bis- (2-ethylhexyl ) ester of benzoic acid, 2phenyl-5-methyl benzoxazole, 2,2'-hydroxy-5-methyl-phenyl benzotriazole, 2- (2-hydroxy-5'-t-octylphenyl) benzotriazole, 2 - (2'-hydroxy-5'-methyphenyl) benzotriazole; dibenzazine; dianisoylmethane, 4-methoxy-4-tbutylbenzoylmethane; 5- (3,3dimethyl-2-norbornylidene) -3-pentan-2-one; the family of derivatives of diphenylacrylate such as 2-ethylhexyl 2-cyano-3,3-diphenyl-2-propenoate, ethyl 2-cyano-3,3diphenyl-2-propenoate; the family of polysiloxanes such as benzylidene siloxane malonate.
    Among the inorganic sunscreens, also called mineral screens, which can be associated with said self-reversible reverse latex as defined above in said compositions (F) and (G), there are titanium oxides, oxides of zinc, cerium oxide, zirconium oxide, yellow, red or black iron oxides, chromium oxides. These mineral screens can be micronized or not, have undergone or not surface treatments and may be presented in the form of aqueous or oily predispersions.
    A subject of the invention is finally the use of said composition (C e ), as defined above, as an agent for reversing a reverse latex of a crosslinked anionic polyelectrolyte (P) comprising for 100% by molar:
    (ai) - of a proportion greater than or equal to 30 mol% and less than or equal to 100 mol%, of monomeric units derived from 2-methyl acid 2 - [(1-oxo 2-propenyl) amino] 1 -propanesulfonic in free or partially or totally salified acid form;
    (a 2 ) - optionally of a proportion greater than 0 mol% and less than or equal to 70 mol%, of monomeric units derived from at least one monomer chosen from the elements of the group consisting of acrylic acid, the methacrylic acid, 2-carboxyethyl acrylic acid, itaconic acid, maleic acid, 3-methyl 3 [(1-oxo 2-propenyl) amino] butanoic acid, the carboxylic function of said monomers being in acid form free, partially salified or totally salified and / or from the elements of the group consisting of (2-hydroxyethyl acrylate), (2,3dihydroxy propyl) acrylate, (2-hydroxy ethyl methacrylate), (2,3dihydroxypropyl) methacrylate, or vinyl pyrrolidone;
    2018P00095 FR (as) - of a proportion greater than 0 mol% and less than or equal to 1 mol% of monomeric units derived from at least one diethylene or polyethylene crosslinking monomer (AR);
    the sum of said molar proportions in monomeric units according to ai), a 2 ) and as) being equal to 100% molar;
    said reverse latex being a water-in-oil type emulsion (E) comprising for 100% of its mass:
    a) - from 10% by mass to 90% by mass, of said crosslinked anionic polyelectrolyte (P);
    b) - From 5% by mass to 50% by mass, of a fatty phase consisting of at least one oil (H),
    c) - From 1% by mass to 50% by mass of water, and
    d) - From 0.5% by mass to 10% by mass of an emulsifier system of the water-oil type (Si).
    the sum of the mass proportions of compounds according to a), b), c) and d) being equal to 100% by mass.
    The following examples illustrate the invention without, however, limiting it.
    I- Preparation of surfactant compositions according to the invention and comparatives
    Ia- Preparation of the composition (EM 2 ) based on decaglycerol laurate (EM1) and hexaglycerol
    71.5 grams of decaglycerol monolaurate sold under the brand name DECAGLYN 1-L (hereinafter denoted by) are introduced into a double-jacketed glass reactor, in which a heat transfer fluid circulates, and provided with effective mechanical stirring. the term “Composition (EM1)”), and 28.5 grams of polyglycerol-6 (sold under the brand name Polyglycerol6 ™ by the company SPIGA), at a temperature of 35 ° C. under mechanical agitation of the anchor type at a speed of 80 rpm. After mixing under such conditions for 30 minutes, the mixture is drained to obtain the composition (EM 2 ).
    Ib- Preparation of the composition (EM3) based on decaglycerol laurate (EM1) and decaglycerol
    71.5 grams of decaglycerol monolaurate marketed under the brand name DECAGLYN 1-L are introduced into a double-jacketed glass reactor, in which a heat transfer fluid circulates, and provided with effective mechanical stirring.
    2018P00095 FR (hereinafter referred to as “Composition (EMi)”), and 28.5 grams of polyglycerol-10 (sold under the brand name Polyglycerin 10 ™), at a temperature of 35 ° C with mechanical stirring anchor type at a speed of 80 revolutions / minute. After mixing under such conditions for 30 minutes, the mixture is drained to obtain the composition (EM 3 ).
    The analytical characteristics of the compositions (EMi), (EM 2 ) and (EM 3 ) are recorded in Table 1 below.
    Table 1
    Emulsifying composition(EMi) (EM 2 ) (EM 3 ) Component proportions (% by mass) Decaglycerol monolaurate 100% 71.5% 71.5% Mass proportion of hexaglycerol 0% 28.5 0% Mass proportion of decaglycerol 0% 0% 28.5
    II- Preparation and evaluation of self-reversible reverse latexes of a crosslinked terpolymer of the sodium salt of 2-methyl - [(1-oxo-2-propenyl) amino] 1propanesulfonic acid of acrylamide and of acid partially salified acrylic and a self-reversible reverse latex of a crosslinked copolymer of the sodium salt of 2-methyl - [(1-oxo-2-propenyl) amino] 1-propanesulfonic acid and acrylamide.
    Il- a) - An aqueous phase is prepared by pouring successively into a beaker and with stirring 277 grams of a commercial solution at 50% by weight of acrylamide, 375 grams of an aqueous solution at 55% of sodium salt of 2methyl - [(1-oxo-2-propenyl) amino] 1-propanesulfonic acid, 10.8 grams of glacial acrylic acid, 0.058 grams of methylene bis (acrylamide), 0.45 grams of a 40% commercial aqueous solution % by mass of diethylenetriamine penta-sodium acetate, and 5.3 grams of an aqueous solution at 48% by mass of sodium hydroxide to adjust the pH of this aqueous phase to 5.3.
    An organic phase is independently prepared by mixing 130 grams of polyisobutene, 90 grams of lsopar ™ H, 30 grams of Marcol ™ 52.17.0 grams
    2018P00095 FR of Montané ™ 70, 5 grams of Simaline ™ IE 200 and 0.2 grams of azo bis (isobutyronitryl) (AIBN).
    The prepared aqueous phase is then gradually added to the oily phase and then dispersed using an Ultra Turrax type rotor stator sold by the company Ika.
    The emulsion obtained is transferred to a reactor to be subjected to a nitrogen sparge to remove the oxygen and cooled to approximately 5-6 ° C. 5 cm 3 of a solution at 0.42% by mass of cumene hydroperoxide in ISOPAR ™ H are added to the emulsion maintained with stirring, then an aqueous solution at 0.1% by mass of sodium metabisulfite is introduced gradually at a rate of 0.5 cm 3 per minute to initiate the polymerization reaction. The temperature of the medium increases until it reaches a plateau.
    After holding at 80 ° C. for one hour, the lsopar ™ H is removed from the reaction medium by distillation under partial vacuum, as well as most of the water. The reaction medium is then cooled to around 35 ° C to obtain the mixture noted (Mi).
    The mixture (Mi) previously obtained is divided into different portions to which are added the different surfactant compositions (EMi), (EM2) and (EM3), as described above, previously heated to 60 ° C, in mass proportions such as shown in Table 2 below.
    The self-reversible reverse latexes resulting from these mixtures are respectively noted (Lh), (LI2), and (LI3) are evaluated by observing their appearance at 25 ° C., by the rate of inversion during the preparation of an aqueous gel at 2% by mass of self-reversible reverse latex (the method of which is described below), by the viscosity of this aqueous gel at 2% by mass of a self-reversible reverse latex.
    The method of evaluating the duration of inversion of self-reversible reverse latexes consists in introducing into a 2-liter beaker, the amount of water necessary for the preparation of an aqueous gel of 800 grams. A mechanical agitator propeller of the Turbotest ™ type, version 2004 marketed by the company VMI, is connected to the bottom of the beaker, connected to a motor. Stirring is started at a speed of 900 revolutions / minute and the necessary quantity of self-reversible reverse latex to be evaluated is introduced into the beaker with stirring. The agitation creates a vortex which disappears when the polymer reverses and the gel forms. The inversion time, measured in seconds, of the self-reversible reverse latexes corresponds to the time elapsed between the start of the addition of the tested self-reversible reverse latex and the disappearance of the vortex, leading to the production of a smooth gel. , free of lumps. This evaluation is carried out after the manufacture of the
    2018P00095 FR reverse latexes tested (t = 0), then after a storage period of 2 months at 25 ° C (t = 2 months). The results obtained are reported in Table 2 below. The viscosity of an aqueous gel at 2% by mass of self-reversible reverse latex (μ), is measured at t = 0 then at t = 2 months, using a Brookfield RVT viscometer (Mobile 6 Speed 5). Similarly, the appearance of the self-reversible reverse latex is visually evaluated at t = 0.
    Table 2
    Self-reversing reverse latexes(Lh) (LI2) (Lh)Reference of the surfactant composition tested(EM1) (EM 2 ) (EM 3 ) Quantity tested (EMi) / (LH) (% by mass) 5% 7% 7%Measures at t = 0 μ (in mPas) 91.000 90,000 75,000 Inversion time 82s 22s 14s Self-reversible latex appearance at 25 ° C EH * EH * EH *Measurements at t = 2 months μ (in mPas) 62,000 65,000 77,000 Inversion time 142S 22s 12s
    EH *: Liquid milky emulsion
    The self-inverting reverse latexes (L1 2 ) and (LI3) according to the invention, and free of alkoxylated derivatives, make it possible to obtain smooth gels, with an inversion time 10 much less than that observed for the self-invert latex -inversible (Lh), comprising only the only decaglycerol monolaurate as a constituent of the inverting surfactant system, while retaining excellent thickening properties. In addition, they are characterized by better reproducibility of the inversion rate and thickening properties after two months of storage than for the comparative self-reversible reverse latex (Lh).
    2018P00095 FR
    III- Preparation and evaluation of self-reversible reverse latexes of a crosslinked copolymer of the sodium salt of 2-methyl - [(1-oxo-2-propenyl) amino] 1propanesulfonic acid and acrylamide.
    An aqueous phase is prepared by pouring successively into a beaker and with stirring 255 grams of a commercial solution at 50% by mass of acrylamide, 272 grams of an aqueous solution at 55% of sodium salt of 2methyl acid - [( 1-oxo-2-propenyl) amino] 1-propanesulfonic, 0.107 gram of methylene bis (acrylamide), 0.45 gram of a 40% by mass commercial aqueous solution of diethylenetriamine penta-sodium acetate, and 45 grams of 'A 48% by mass aqueous solution of sodium hydroxide to adjust the pH of this aqueous phase to 6.0.
    An organic phase is independently prepared by mixing 220 grams of Emogreen ™ L15 and 25 grams of Simaline ™ IE.
    The prepared aqueous phase is then gradually added to the oily phase and then dispersed using an Ultra Turrax type rotor stator sold by the company Ika.
    The emulsion obtained is transferred to a reactor to be sparged with nitrogen to remove oxygen and cooled to about 5-6 ° C. 0.69 gram of sodium persulfate previously dissolved in 2 grams of water is added to the emulsion maintained with stirring, then an aqueous solution at 2.25% n mass of sodium metabisulfite is gradually introduced to initiate the polymerization reaction . The temperature of the medium increases until it reaches a plateau.
    After holding at 80 ° C for three hours, the reaction medium is then cooled to about 35 ° C to obtain the mixture noted (M2).
    The mixture (M2) previously obtained is divided into different portions to which are added the different surfactant compositions (EM1), (EM2) and (EM 3 ), as described above, previously heated to 60 ° C., in mass proportions as shown in Table 3 below.
    The self-reversible reverse latexes resulting from these mixtures are respectively denoted (LI4), (Lis) and (Lie) are evaluated by observing their appearance at 25 ° C., by the rate of inversion during the preparation of an aqueous gel at 2% by mass of self-reversible reverse latex (the method of which is described below), by the viscosity of this aqueous gel at 2% by mass of a self-reversible reverse latex.
    The method of evaluating the duration of inversion of self-reversible reverse latexes consists in introducing into a 2-liter beaker, the amount of water necessary for the preparation of an aqueous gel of 800 grams. A mechanical agitator propeller of the Turbotest ™ type, version 2004 marketed by the
    2018P00095 FR VMI company, connected to a motor. Stirring is started at a speed of 900 revolutions / minute and the necessary quantity of self-reversible reverse latex to be evaluated is introduced into the beaker with stirring. The agitation creates a vortex which disappears when the polymer reverses and the gel forms. The inversion time, measured in seconds, of the self-reversible reverse latexes 5 corresponds to the time elapsed between the start of the addition of the tested self-reversible reverse latex and the disappearance of the vortex, leading to the production of a gel. smooth, free of lumps. This evaluation is carried out after the manufacture of the reverse latexes tested (t = 0). The results obtained are listed in Table 3 below. The viscosity of an aqueous gel at 2% by mass of self-reversible reverse latex 10 (μ), is measured at t = 0 using a Brookfield RVT viscometer (Mobile 6 Speed
    5). Likewise, the appearance of the self-reversible reverse latex is evaluated visually at t = 0.
    Table 2
    Self-reversing reverse latexes(LL) (Lily) (Lie)Reference of the surfactant composition tested(EM1) (EM 2 ) (EM 3 ) Quantity tested (EMi) / (Lli) (% by mass) 5% 7% 7%Measures at t = 0 μ (in mPas) 75,000 101.200 83.600 Inversion time 45s 30s 30s Self-reversible latex appearance at 25 ° C EH * EH * EH *
    EH *: Liquid milky emulsion
    The self-inverting inverse latexes (Lis) and (Lie) according to the invention, and free of alkoxylated derivatives, make it possible to obtain, at t = 0, smooth gels, with a duration of inversion shorter than that observed for the self-reversible reverse latex (Lli), comprising only the only decaglycerol monolaurate as a constituent of the reversing surfactant system, while retaining excellent thickening properties.
    IV: Illustrative cosmetic formulations
    2018P00095 FR
    In the following formulations, the percentages are percentage by mass per 100% of the mass of the formulation. expressed in
    EXAMPLE IV-1: Care cream
    Cyclomethicone: 10% Self-reversible reverse latex (Ll 2 ): 0.8% Montanov ™ 68: 2% Stearyl alcohol: 1% Stearic alcohol: 0.5% Conservative : 0.65% Lysine: 0.025% EDTA (disodium salt): 0.05% Xanthan gum: 0.2% Glycerin: 3% Water: q.s.p. 100%
    EXAMPLE IV-2: Sun milk
    FORMULA
    At Montanov ™ 68: 3.0% Sesame oil : 5.0% PARSOL ™ MCX: 5.0% Carrageenan λ: 0.10% Beautiful : q.s. 100% C Self-reversible reverse latex (Ll 3 ): 0.80% D Perfume: qs Conservative : qs
    OPERATING MODE
    Emulsify B in A at 60 ° C then add C around 60 ° C, then D around 30 ° C and adjust the pH if necessary.
    EXAMPLE IV-3: Body milk
    Montanov ™ 202: 3.5% LANOL ™ 37T: 8.0% SOLAGUM ™ L: 0.05% Water: q.s. 100% Benzophenone-3: 2.0%
    2018P00095 FR
    Dimethicone 350cPs:
    0.05%
    Self-reversible reverse latex (Ll 2 ):
    2.5%
    Conservative :
    0.2%
    Perfume:
    0.4%
    EXAMPLE IV-4: Make-up removing emulsion with sweet almond oil
    Montanov ™ 202:
    Sweet almond oil:
    Water:
    Self-reversible reverse latex (Ll 2 ):
    Glycerin:
    Conservative :
    Perfume:
    EXAMPLE IV-5: Hydrating cream for oily skin
    Montanov ™ 68:
    Cetylstearylctanoate:
    Octyl palmitate:
    Water:
    Self-reversible reverse latex (LI3):
    MICROPEARL ™ M100:
    Mucopolysaccharides:
    SEPICIDE ™ HB:
    Perfume:
    EXAMPLE IV-6: Cleansing milk
    Montanov ™ 68:
    PRIMOL ™ 352:
    Sweet almond oil:
    Water:
    Self-reversible reverse latex (Ll 2 ):
    Conservative :
    EXAMPLE IV-7: Sun milk
    Montanov ™ L:
    LANOL ™ 37T:
    PARSOL ™ MCX:
    5%
    5%
    q.s. 100%
    0.3%
    5%
    0.2%
    0.3%
    5%
    8%
    2%
    q.s. 100%
    2.6%
    3.0%
    5%
    0.8%
    0.3%
    3%
    8.0%
    2%
    q.s. 100%
    0.8%
    0.2%
    3.5%
    10.0%
    5.0%
    2018P00095 FR
    EUSOLEX ™ 4360: 2.0% Water: q.s. 100% Self-reversible reverse latex (Ll 2 ): 1.8% Conservative : 0.2% Perfume: 0.4%
    EXAMPLE IV-8: Sunless tanning emulsion
    LANOL ™ 99: 15% Montanov ™ 68: 3.0% PARSOL ™ MCX: 3.0% Water: q.s. 100% Dihydroxyacetone: 5.0% Monosodium phosphate: 0.2% Self-reversible reverse latex (LI3): 2.5% Perfume: 0.3% SEPICIDE ™ HB: 0.8% Sodium hydroxide : qs pH = 5.
    EXAMPLE IV-9: Care cream
    Cyclomethicone: 10% Self-reversible reverse latex (LI3): 2.8% Montanov ™ 202: 4.5% Conservative : 0.65% Lysine: 0.025% EDTA (disodium salt): 0.05% Xanthan gum: 0.2% Glycerin: 3% Water: qs. 100%
    EXAMPLE IV-10: Sunscreen
    SIMULSOL ™ 165: 3% Montanov ™ 68: 2% Benzoate C12-C15: 8% PECOSIL ™ PS 100: 2% Dimethicone: 2% Cyclomethicone: 5% Octyl para-methoxy cinnamate: 6%
    2018P00095 FR
    Benzophenone-3: 4% Titanium oxide: 8% Xanthan gum : 0.2% Butylene glycol: 5% Demineralized Water : qs 100% Self-reversible reverse latex (LI2): 1.5% Preservative, fragrance: qs
    EXAMPLE IV-11: Sun gel and self-tanner
    Montanov ™ 68: 3.0% Glyceryl triheptanoate: 10.0% DEEPALINE ™ PVB: 1.05% Self-reversible reverse latex (LI3): 2.2% Water: qs 100% Dihydroxyacetone: 5% Perfume: 0.1% SEPICIDE ™ HB: 0.3% SEPICIDE ™ Cl: 0.1% PARSOL ™ MCX: 4.0%
    The definitions of the products used in the examples are as follows: MICROPEARL ™ M 100 is an ultra fine powder with a very soft touch and with a mattifying action sold by the company MATSUMO
    SEPICIDE ™ Cl, imidazolidine urea, is a preservative sold by the company SEPPIC.
    SIMULSOL ™ 165 is self-emulsifiable glycerol stearate sold by the company SEPPIC.
    SEPICIDE ™ HB, which is a mixture of phenoxyethanol, methylparaben, ethylparaben, propylparaben and butylparaben, is a preservative sold by the company SEPPIC.
    PARSOL ™ MCX is octyl para-methoxy cinnamate sold by the company GIVAUDAN.
    LANOL ™ 37T is glycerol triheptanoate, sold by the company SEPPIC. SOLAGUM ™ L is a carrageenan sold by the company SEPPIC.
    EUSOLEX ™ 4360 is a solar filter sold by the company MERCK.
    2018P00095 FR
    DEEPALINE ™ PVB, is a hydrolyzate of acylated wheat proteins marketed by the company SEPPIC.
    PRIMOL ™ 352 is a mineral oil sold by the company EXXON. PECOSIL ™ PS 100 is Dimethicone PEG-7 sold by the company PHOENIX.
    Montanov ™ 68 (INCI name Cetearyl Alcohol (and) Cetearyl Glucoside) is an emulsifying agent sold by the company SEPPIC
    Montanov ™ L (INCI name C14-22 Alcohols (and) C12-20 Alkyl Glucoside) is an emulsifying agent sold by the company SEPPIC.
    Montanov ™ 202 (INCI name Arachidyl Alcohol & Behenyl Alcohol & Arachidyl)) is an emulsifying agent sold by the company SEPPIC.
    权利要求:
    Claims (10)
    [1" id="c-fr-0001]
    1. Self-reversible reverse latex of a crosslinked anionic polyelectrolyte (P) comprising, for 100% molar:
    (ai) - of a proportion greater than or equal to 25 mol% and less than or equal to 80 mol%, of monomeric units derived from 2-methyl acid 2 - [(1-oxo 2-propenyl) amino] 1 -propanesulfonic in free or partially or totally salified acid form;
    (a 2 ) - of a proportion greater than or equal to 20 mol% and less than or equal to 75 mol%, of monomeric units derived from at least one monomer chosen from the elements of the group consisting of acrylamide, Ν , Ν-dimethyl acrylamide; methacrylamide or N-isopropyl acrylamide;
    (a 3 ) - optionally of a proportion greater than 0 mol% and less than or equal to 10 mol%, of monomeric units derived from at least one monomer chosen from the elements of the group consisting of acrylic acid, the methacrylic acid, 2-carboxyethyl acrylic acid, itaconic acid, maleic acid, 3-methyl 3 [(1-oxo 2-propenyl) amino] butanoic acid, the carboxylic function of said monomers being in acid form free, partially salified or fully salified;
    (a 4 ) - of a proportion greater than 0 mol% and less than or equal to 1 mol% of monomeric units derived from at least one diethylenic or polyethylene crosslinking monomer (AR);
    the sum of said molar proportions in monomeric units according to ai), a 2 ) a 3 ) and a 4 ) being equal to 100 mol%;
    said self-reversible reverse latex being a water-in-oil type emulsion (E) comprising for 100% of its mass:
    a) - from 10% by mass to 90% by mass, of said crosslinked anionic polyelectrolyte (P);
    b) - From 5% by mass to 50% by mass, of a fatty phase consisting of at least one oil (H),
    c) - From 1% by mass to 50% by mass of water,
    d) - From 0.5% by mass to 10% by mass of an emulsifier system of the water-oil (Si) type, and
    e) - From 2% by mass to 10% by mass of an emulsifying system of the oil-in-water type (S 2 );
    2018P00095 FR the sum of the mass proportions of compounds according to a), b), c), d) and e) being equal to 100% by mass;
    said self-reversible reverse latex being characterized in that said oil-in-water type emulsifying system (S 2 ) comprises for 100% of its mass:
    f) - A proportion greater than or equal to 50% by mass and less than or equal to 100% of a composition (Ce) which comprises for 100% of its mass:
    ei) - From 10% by mass to 60% by mass of at least one compound of formula (I): HO- [CH 2 -CH (OH) -CH 2 -O] n -H (I) in which n represents a whole number greater than or equal to one and less than or equal to fifteen;
    e 2 ) - From 40% by mass to 90% by mass of at least one compound of formula (II)
    Ri- (C = O) - [O-CH 2 -CH (OH) -CH 2 ] P -OH (II), in which p, different or identical to n, represents an integer greater than or equal to one and less or equal to fifteen; and in which the group Ri- (C = O) - represents a saturated or unsaturated, linear or branched aliphatic radical, comprising from six to twenty two carbon atoms, and optionally e 3 ) - Up to 30% by mass of at least a composition (Cn) represented by formula (III):
    HO- [CH 2 -CHOH-CH 2 -O-] q- (G) rH (III), in which q different or identical to n, represents an integer greater than or equal to one and less than or equal to 3, G represents the remainder of a reducing sugar and r represents a decimal number greater than or equal to 1.05 and less than or equal to 5.00, said composition (Cn) consisting of a mixture of the compounds of formulas (llli), (lll 2 ), (lll 3 ), (lll 4 ) and (lll 5 ):
    HO- [CH 2 -CHOH-CH 2 -O-] q -O- (G) iH (III ·),
    HO- [CH 2 -CHOH-CH 2 -O-] q -O- (G) 2 -H (lll 2 ),
    HO- [CH 2 -CHOH-CH 2 -O-] q -O- (G) 3 -H (I ll 3 ),
    HO- [CH 2 -CHOH-CH 2 -O-] q -O- (G) 4 -H (lll 4 ),
    HO- [CH 2 -CHOH-CH 2 -O-] q -O- (G) 5 -H (Ill 5 ), in molar proportions as said compounds of formulas (III1), (lll 2 ), (lll 3 ), (lll 4 ) and (1115) respectively equal to ai, a 2 , a 3 , a 4 and as, such that the sum (ai + a 2 + a 3 + a 4 + as) is equal to one, and that the sum (ai + 2a 2 + 3a 3 + 4a 4 + 5as) is equal to r;
    the sum of the mass proportions of compounds according to ei), e 2 ) and e 3 ) being equal to 100% by mass.
    2018P00095 FR
    [2" id="c-fr-0002]
    2. Self-reversible reverse latex as defined in claim 1, characterized in that said crosslinked anionic polyelectrolyte (P) is a copolymer crosslinked by triallylamine and / or methylene-bis (acrylamide), 2- methyl 2 - [(1-oxo 2propenyl) amino] 1-propanesulfonic partially or totally salified in the form of sodium salt or ammonium salt and acrylamide; a copolymer crosslinked with triallylamine and / or methylene-bis (acrylamide), 2-methyl 2 - [(1-oxo 2propenyl) amino] 1-propanesulfonic acid (γ) partially or totally salified in the form of a salt sodium, and acrylamide (ε), in a molar ratio (γ) / (ε) greater than or equal to 30/70 and less than or equal to 90/10; a copolymer crosslinked with triallylamine and / or methylene-bis (acrylamide), 2-methyl 2 - [(1-oxo 2-propenyl) amino] 1propanesulfonic acid (γ) partially or totally salified in the form of a salt sodium, and acrylamide, (ε) in a molar ratio (γ) / (ε) greater than or equal to 40/60 and less than or equal to 90/10; a terpolymer crosslinked with triallylamine and / or methylenebis (acrylamide), 2-methyl 2 - [(1-oxo 2-propenyl) amino] 1-propanesulfonic acid partially or totally salified in the form of sodium salt or ammonium salt, acrylamide and acrylic acid partially or fully salified in the form of sodium salt or ammonium salt; a terpolymer crosslinked with triallylamine and / or methylene-bis (acrylamide), 2-methyl 2 - [(1-oxo 2-propenyl) amino] 1propanesulfonic acid partially or totally salified in the form of sodium salt or ammonium salt in a molar proportion greater than or equal to 30% and less than or equal to 45%, acrylamide in a molar proportion greater than or equal to 45% and less than or equal to 68% and acrylic acid partially or totally salified in the form of sodium salt or ammonium salt in a molar proportion greater than or equal to 2% and less than or equal to 10%, or a terpolymer crosslinked by triallylamine and / or methylene-bis (acrylamide) , 2-methyl 2 - [(1-oxo 2propenyl) amino] 1-propanesulfonic acid partially or totally salified in the form of sodium salt or ammonium salt in a molar proportion greater than or equal to 30% and less or equal to 45%, of acryl ide in a molar proportion greater than or equal to 47% and less than or equal to 68% and acrylic acid partially or totally salified in the form of sodium salt or ammonium salt in a molar proportion greater than or equal to 2% and less than or equal to 8%.
    [3" id="c-fr-0003]
    3. Self-reversible reverse latex as defined in any one of claims 1 or 2, characterized in that in the formula (I) as defined above, n represents an integer greater than or equal to one and less than or equal to ten, and in that in formula (II) as defined above, p, identical or different from n,
    2018P00095 FR represents an integer greater than or equal to one and less than or equal to ten, and the group Ri- (C = O) - is chosen from the radicals octanoyl, decanoyl, ω-undecylenoyl, dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, 9-octadecenoyl or 9,12octadecadienoyl.
    [4" id="c-fr-0004]
    4. Self-reversible reverse latex as defined in any one of claims 1 to 3, characterized in that in said emulsifier system of oil-in-water type (S 2 ) said composition (C e ) as defined above , consists of, for 100% of its mass:
    ei) - From 10% by mass to 60% by mass of at least one compound of formula (I) as defined above and e 2 ) - From 40% by mass to 90% by mass of at least one compound of formula (II) as defined above.
    [5" id="c-fr-0005]
    5. Self-reversible reverse latex as defined in any one of claims 1 to 3, characterized in that in the formula (III) as defined above, q is equal to one, G represents the remainder of the glucose and r represents a decimal number greater than or equal to 1.05 and less than or equal to 2.5.
    [6" id="c-fr-0006]
    6. Self-reversible reverse latex as defined in any one of claims 1 to 3 or 5, characterized in that in said oil-in-water type emulsifying system (S 2 ), said composition (C e ) as defined previously consists of, for 100% of its mass:
    ei) - From 5% by mass to 15% by mass of at least one compound of formula (I) as defined above, e 2 ) - From 60% by mass to 80% by mass of at least one compound of formula (II) as defined above, and e 3 ) - From 5% to 15% by mass of at least one composition (Ou) represented by formula (III) as defined above.
    [7" id="c-fr-0007]
    7. self-reversible reverse latex as defined in any one of claims 1 to 6, characterized in that said emulsifying system of oil-in-water type (S 2 ) is said composition (C e ) as defined above .
    2018P00095 FR
    [8" id="c-fr-0008]
    8. Use of said self-reversible reverse latex as defined in one of claims 1 to 7, as a thickening and / or emulsifier and / or stabilizer of a topical cosmetic composition.
    5
    [9" id="c-fr-0009]
    9. Topical cosmetic composition (F), characterized in that it comprises, as thickening agent, for 100% of its total mass between 0.1% and 10% by mass of said self-reversible reverse latex, as defined in one of claims 1 to 7.
    [10" id="c-fr-0010]
    10. Topical pharmaceutical composition (G) characterized in that it comprises 10 as thickening agent, for 100% of its total mass between 0.1% and 10% by mass of said self-reversible reverse latex as defined in one of claims 1 to 7.
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    同族专利:
    公开号 | 公开日
    KR20200140343A|2020-12-15|
    JP2021519778A|2021-08-12|
    WO2019193294A1|2019-10-10|
    US20210378938A1|2021-12-09|
    EP3774949A1|2021-02-17|
    CN112135847A|2020-12-25|
    FR3079837B1|2020-03-13|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    EP1055451A1|1999-05-28|2000-11-29|Societe D'exploitation De Produits Pour Les Industries Chimiques, S.E.P.P.I.C.|Use of alkylglycosides as inverter of polymer emulsions, method of inverting them, self-invertible inverted latex and industrial use thereof|
    WO2009156691A2|2008-06-27|2009-12-30|Société d'Exploitation de Produits pour les Industries Chimiques SEPPIC|Novel inverse latices that are free of oxyethylene derivatives, and cosmetic, dermocosmetic, dermopharmaceutical or pharmaceutical compositions comprising same|
    WO2009156690A2|2008-06-27|2009-12-30|Société d'Exploitation de Produits pour les Industries Chimiques SEPPIC|Novel inverse latices based on fatty alcohol ethers, and cosmetic, dermocosmetic, dermopharmaceutical or pharmaceutical compositions comprising same|
    FR2721607B1|1994-06-28|1996-10-31|Seppic Sa|New quaternary ammonium derivatives, their preparation process and their use as surfactants.|
    FR2761595B1|1997-04-04|1999-09-17|Oreal|COMPOSITIONS COMPRISING SANTALINES, SANTARUBINS FOR ARTIFICIAL COLORING OF THE SKIN AND USES THEREOF|
    WO2003103616A2|2002-06-11|2003-12-18|L'oreal|Use of an agent mimicking dopachrome tautomerase activity as protective agent for hair follicle melanocytes and uses thereof|
    FR2959746B1|2010-05-06|2012-06-15|Soc Dexploitation De Produits Pour Les Industries Chimiques Seppic|NEW AUTO-INVERSIBLE REVERSE LATEX, ITS USE AS A THICKENING AGENT IN A COSMETIC COMPOSITION|
    FR2992323B1|2012-06-25|2015-07-03|Soc Dexploitation De Produits Pour Les Industries Chimiques Seppic|NEW SURFACE-FREE REVERSE LATEX FREE OF SURFACTANT, ITS USE AS A THICKENING AGENT IN A COSMETIC COMPOSITION|WO2021091174A1|2019-11-06|2021-05-14|주식회사 엘지에너지솔루션|Binder for lithium secondary battery electrode, lithium secondary battery positive electrode comprising same, and lithium secondary battery|
    FR3104160B1|2019-12-09|2021-12-10|Soc Dexploitation De Produits Pour Les Industries Chimiques Seppic|Inverse latex for cosmetic composition combining EDDS as a sequestering agent and a polyelectrolyte comprising AMPS and acrylamide|
    FR3104163B1|2019-12-09|2021-12-17|Soc Dexploitation De Produits Pour Les Industries Chimiques Seppic|Inverse latex for cosmetic composition combining the tetrasodium salt of N, N diacetic glutamic acid as a sequestering agent and a polyelectrolyte comprising AMPS and acrylamide|
    法律状态:
    2019-04-18| PLFP| Fee payment|Year of fee payment: 2 |
    2019-10-11| PLSC| Publication of the preliminary search report|Effective date: 20191011 |
    2020-04-20| PLFP| Fee payment|Year of fee payment: 3 |
    2021-04-23| PLFP| Fee payment|Year of fee payment: 4 |
    优先权:
    申请号 | 申请日 | 专利标题
    FR1853012A|FR3079837B1|2018-04-06|2018-04-06|SELF-REVERSIBLE REVERSE LATEX COMPRISING POLYGLYCEROL ESTERS, ITS USE AS A THICKENER AND COSMETIC COMPOSITIONS COMPRISING SAME|
    FR1853012|2018-04-06|FR1853012A| FR3079837B1|2018-04-06|2018-04-06|SELF-REVERSIBLE REVERSE LATEX COMPRISING POLYGLYCEROL ESTERS, ITS USE AS A THICKENER AND COSMETIC COMPOSITIONS COMPRISING SAME|
    CN201980033098.1A| CN112135847A|2018-04-06|2019-04-04|Self-reversible reverse latex comprising polyglycerol esters, use thereof as thickening agent, and cosmetic composition comprising same|
    JP2020552826A| JP2021519778A|2018-04-06|2019-04-04|Self-reversible reverse latex containing polyglycerol ester, its use as a thickener, and cosmetic compositions containing it|
    US17/044,733| US20210378938A1|2018-04-06|2019-04-04|Self-invertible inverse latex comprising polyglycyerol esters, use thereof as a thickening agent, and cosmetic compositions comprising same|
    EP19722167.4A| EP3774949A1|2018-04-06|2019-04-04|Self-invertible inverse latex comprising polyglycyerol esters, use thereof as a thickening agent, and cosmetic compositions comprising same|
    KR1020207031909A| KR20200140343A|2018-04-06|2019-04-04|Self-reversible inverse latex comprising polyglycerol ester, its use as a thickener, and cosmetic composition comprising the same|
    PCT/FR2019/050798| WO2019193294A1|2018-04-06|2019-04-04|Self-invertible inverse latex comprising polyglycyerol esters, use thereof as a thickening agent, and cosmetic compositions comprising same|
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