EP2645989A1 - Novel electrolyte-resistant cationic thickeners usable over a wide ph range, method for preparing same, and composition containing same - Google Patents

Novel electrolyte-resistant cationic thickeners usable over a wide ph range, method for preparing same, and composition containing same

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Publication number
EP2645989A1
EP2645989A1 EP11799790.8A EP11799790A EP2645989A1 EP 2645989 A1 EP2645989 A1 EP 2645989A1 EP 11799790 A EP11799790 A EP 11799790A EP 2645989 A1 EP2645989 A1 EP 2645989A1
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EP
European Patent Office
Prior art keywords
equal
less
monomeric units
molar proportion
inverse latex
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP11799790.8A
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German (de)
French (fr)
Inventor
Olivier Braun
Paul Mallo
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA
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Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA
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Publication of EP2645989A1 publication Critical patent/EP2645989A1/en
Withdrawn legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/064—Water-in-oil emulsions, e.g. Water-in-silicone emulsions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/52—Amides or imides
    • C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F20/56—Acrylamide; Methacrylamide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/002—Preparations for repairing the hair, e.g. hair cure
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/32—Polymerisation in water-in-oil emulsions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/12—Powdering or granulating
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/24—Homopolymers or copolymers of amides or imides
    • C08L33/26—Homopolymers or copolymers of acrylamide or methacrylamide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/48—Thickener, Thickening system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes

Definitions

  • New cationic thickeners resistant to electrolytes and usable over a wide pH range process for their preparation and composition containing.
  • the invention relates to novel polymeric cationic thickeners their process of preparation as well as their use as thickening and / or emulsifying agent.
  • the thickening of the aqueous phases is generally carried out by incorporating hydrophilic polymers of all kinds, whether synthetic or of natural origin.
  • xanthan or guar gums are fairly widely used. However, they have the classic disadvantages of natural products, namely a quality and a fluctuating price.
  • hydrophilic synthetic thickeners are polymers in the form of powders or inverse self-reversing latexes. They are implemented in a wide pH range and are often well tolerated by humans. Such compositions are described, for example, in the US Pat. Nos. 5,004,598, 6,197,287, 6,136,305, 6,346,239 or in the European patent application published under the number EP 0 503 853.
  • These polymers are anionic and are therefore essentially intended to thicken aqueous phases containing the various conventional constituents that can be found in topical formulations of the cosmetic, dermopharmaceutical or pharmaceutical industry.
  • These include oils, surfactants (nonionic or anionic) also called emulsifiers, mineral salts, weak acids.
  • formulations intended in particular for hair care contain cationic surfactants and cationic conditioning polymers.
  • anionic polymer thickeners are not recommended because of the electrostatic interactions between the positive and negative charges that cause precipitation of the polymer, and cationic thickening polymers such as those described in the published US patents are preferably used. under US 4,806,345 and US 5, 100,660.
  • composition for treating hair comprising a copolymer of 20% to 90% by weight of N-hydroxyalkyl acrylamide and 10% to 80% by weight of a cationic monomer.
  • the subject of the invention is an inverse latex comprising a cationic, linear, branched or crosslinked polyelectrolyte resulting from the polymerization for 100 mol%:
  • n represents, independently of one another, a number of between 1 and 50
  • A represents an unsaturated aliphatic monovalent radical comprising from 2 to 6 carbon atoms
  • R 1 represents a hydrogen atom, a methyl radical or a ethyl radical and R represents a linear or branched, saturated or unsaturated hydrocarbon-based aliphatic radical comprising from 8 to 30 carbon atoms
  • d) optionally of a molar proportion greater than 0% and less than or equal to 10% and of monomeric units derived from at least one neutral monomer different from said N- (2-hydroxyethyl) acrylamide, it being understood that this molar proportion is strictly lower than that of monomeric units derived from N- (2-hydroxyethyl) acrylamide, and
  • e optionally of a molar proportion greater than 0% and less than or equal to 1% of a diethylenic or polyethylenic crosslinking monomer.
  • inverse latex frame of the present invention, a water-in-oil emulsion of the polyelectrolyte as defined above.
  • connected polyelectrolyte denotes a nonlinear polyelectrolyte which has pendant chains so as to obtain, when dissolved in water, a high state of entanglement leading to viscosities with a low rate of gradient, very important.
  • Crosslinked polyelectrolyte means a nonlinear polyelectrolyte in the form of a three-dimensional network which is insoluble in water but swellable in water and conducts therefore to obtain a chemical gel.
  • the "water-in-oil" emulsifier system (W / O) consists of either a single surfactant or a mixture of surfactants, provided that said surfactant or said mixture has a low enough HLB value to induce a water-in-oil emulsion.
  • sorbitan esters such as sorbitan oleate, marketed by the company SEPPIC under the name MONT ANE TM 80, sorbitan isostearate, sold by the company SEPPIC under the name MONTANE TM 70 or sesquioleate sorbitan marketed by the company SEPPIC under the name MONTANE TM 83.
  • polyethoxylated sorbitan esters for example the pentaethoxylated sorbitan mono-oleate marketed by the company SEPPIC under the name MONTANOX TM 81 or pentaethoxylated sorbitan isostearate marketed under the name MONTANOX TM 71 by the company SEPPIC.
  • polyesters of molecular weight between 1000 and 3000 products of the condensation between a poly (isobutenyl) succinic acid or its anhydride and such as the HYPERMER TM 2296 marketed by UNIQEMA or finally the weight block copolymers molecular between 2500 and 3500, such as HYPERMER TM B246 marketed by the company UNIQEMA or SIMALINE TM IE 200 marketed by the company SEPPIC.
  • the inverse latex as defined above generally comprises between 0.5% by weight and 10% by weight of said "water-in-oil" emulsifier system.
  • the inverse latex generally contains between 1% and 50% by weight of water.
  • the oil phase of the self-invertible inverse latex described above consists of:
  • a mineral oil or a mixture of mineral oils, containing paraffin-type saturated hydrocarbons, isoparaffin, cycloparaffin, having at room temperature, a density between 0.7 and 0.9 and a higher boiling point; at 180 ° C, such as, for example, ISOPAR TM M or ISOPAR TM L, EXXOL TM D 100 S sold by EXXON or mineral white oils in compliance with FDA 21 CFR 172.878 and FR 178.3620 (a) regulations. such as MARCOL TM 52 or MARCOL TM 82, also marketed by EXXON;
  • the inverse latex as defined above generally comprises, for 100% by weight, from 5% to 50% by weight of oil.
  • cationic monomer primarily an aliphatic monomer having a quaternary ammonium function and less an unsaturated carbon-carbon bond. Such a monomer is generally available in particular in the form of salts.
  • salts denotes, more particularly, halides, such as bromides, chlorides or iodides, of said quaternary ammonium-functional monomers.
  • the subject of the invention is an inverse latex as defined above, for which the monomeric units originating from at least one cationic monomer, constitutive of said cationic polyelectrolyte, are derived from the following quaternary ammonium salts:
  • MAMPTAC TM Le, ⁇ , ⁇ -trimethyl-3 - [(2-methyl-1-oxo-2-propenyl) amino] propanammonium chloride
  • API TM APITAC TM
  • DMAC TM Diallyl dimethylammonium chloride
  • a chain consisting of at least two different groups selected from ethoxyl propoxyl and / or butoxyl groups. When this chain is composed of different groups, they are distributed throughout this chain, sequentially or randomly.
  • neutral monomer different from said N- (2-hydroxyethyl) acrylamide there is meant monomers having no strong or weak acid function or positively charged group. They are more particularly chosen from vinylpyrrolidone, diacetoneacrylamide, ⁇ , ⁇ -dimethylacrylamide, or N- [2-hydroxy-1,1-bis (hydroxymethyl) ethyl] propenamide [or tris (hydroxymethyl) acrylamidomethane or N- [tris (hydroxymethyl) methyl] acrylamide also called THAM].
  • R denotes more particularly in formula (I) as defined above:
  • a radical derived from linear primary alcohols such as, for example, those derived from octyl, pelargonic, decylic, undecylic, undecenyl, lauric, tridecyl, myristyl, pentadecyl, cetyl, heptadecyl, stearyl, oleyl, linoleyl, nonadecyl, arachidic alcohols, behenyl, erucylic or l-triacontanoic.
  • p represents an integer between 2 and 14, such as, for example, the 2-ethyl hexyl, 2-propyl heptyl, 2-butyl octyl, 2-pentyl nonyl, 2-hexyl decyl or 2-octyl dodecyl radicals; ;
  • m represents an integer from 2 to 26 such as, for example, 4-methyl pentyl, 5-methyl hexyl, 6-methyl heptyl, 15-methyl pendadecyl or 16-methyl heptadecyl;
  • linear or branched, saturated or unsaturated, hydrocarbon-based aliphatic radical comprising from 8 to 30 carbon atoms, more particularly denotes for R; in the formula (I) as defined above, an alkyl radical containing from 8 to 18 carbon atoms.
  • n represents more particularly a number between 4 and 25.
  • the cationic polyelectrolyte as defined above is characterized in that the molar proportion of monomeric units originating from the cationic monomer or monomers is between 70% and 95%, more particularly between 75% and 95%.
  • the subject of the invention is an inverse latex as defined above, for which said monomeric units originating from at least one cationic monomer, constitutive of said cationic polyelectrolyte, are solely derived from a salt of ⁇ , ⁇ , ⁇ -trimethyl-3 - [(1-oxo-2-propenyl) amino] propanammonium and in particular ⁇ , ⁇ , ⁇ -trimethyl-3 - [(1-oxo-2-propenyl) amino] propanammonium chloride (APTAC TM).
  • the polyelectrolyte as defined above is characterized in that the molar proportion in monomeric units derived from N- (2-hydroxyethyl) acrylamide is greater than or equal to 1% and less than 20%.
  • the polyelectrolyte as defined above is characterized in that the molar proportion in monomeric units derived from the compound of formula (I) as defined above, is greater than or equal to 0.1 % and less than or equal to 15%, more particularly greater than or equal to 0.5% and less than or equal to 10%.
  • the invention more particularly relates to an inverse latex as defined above, in which the cationic polyelectrolyte, linear, connected or crosslinked, is derived from the polymerization for 100 mol%:
  • n represents, independently of one another, a number of between 1 and 50
  • A represents an unsaturated aliphatic monovalent radical comprising from 2 to 6 carbon atoms
  • R 1 represents a hydrogen atom, a methyl radical or a ethyl radical and R represents a linear or branched, saturated or unsaturated hydrocarbon-based aliphatic radical comprising from 8 to 30 carbon atoms
  • d) optionally with a molar proportion greater than 0% and less than or equal to 10% and of monomeric units derived from at least one neutral monomer different from said N- (2-hydroxyethyl) acrylamide, it being understood that this molar proportion is strictly lower than that of the monomeric units derived from N- (2-hydroxyethyl) ) acrylamide, and
  • e optionally of a molar proportion greater than or equal to 0.005% and less than or equal to 1% of a diethylenic or polyethylene crosslinking monomer.
  • the cationic polyelectrolyte as defined above is crosslinked.
  • the invention more particularly relates to an inverse latex as defined above, for which said diethylenic or polyethylenic or polyelectrolyte crosslinking monomer is chosen from diallyloxyacetic acid or its sodium or potassium salt.
  • said diethylenic or polyethylenic or polyelectrolyte crosslinking monomer is chosen from diallyloxyacetic acid or its sodium or potassium salt.
  • said diethylenic or polyethylene crosslinking monomer or polyelectrolyte is methylene bis (acrylamide).
  • said diethylenic or polyethylenic crosslinking monomer or polyelectrolyte is used in the molar proportion, expressed relative to the monomers used, greater than 0.05%, more particularly 0.01% to 0.2%. % and most preferably from 0.01% to 0.1%.
  • the crosslinking agent used is methylene bis (acrylamide).
  • the compound of formula (I) as defined above is chosen from:
  • Tetraethoxylated lauryl acrylate which compound corresponds to the formula (I) as defined above, in which R represents the dodecyl radical, A represents the vinyl radical, R 1 represents a hydrogen atom and n is equal to 4.
  • Eicosaethoxylated stearyl methacrylate compound of formula (I) as defined above, in which R represents the stearyl radical, A represents the isopropenyl radical, R 1 represents a hydrogen atom and n is equal to 20, or
  • Tetraethoxylated lauryl methacrylate which compound corresponds to formula (I) as defined above, in which R represents the dodecyl radical, A represents the isopropenyl radical and n is equal to 4.
  • the inverse latex as defined previously is derived from the polymerization for 100 mol%:
  • the inverse latex as defined above further comprises an emulsifier system of the "oil-in-water” type.
  • Said "oil-in-water emulsifier system" (O / W) consists of either a single surfactant or a surfactant mixture, provided that said surfactant or mixture has a HLB value high enough to induce oil-in-water emulsion.
  • O / W oil-in-water emulsifier system
  • Ethoxylated sorbitan esters such as polyethoxylated sorbitan oleate with 20 moles of ethylene oxide marketed by the company SEPPIC under the name MONTANOX TM 80 or polyethoxylated sorbitan laurate with 20 moles of ethylene oxide marketed by the company SEPPIC under the name MONTANOX TM 20;
  • Decaethoxylated oleodecyl alcohol marketed by SEPPIC under the name SIMULSOL TM OC 710;
  • the inverse latex as defined above is then self-invertible; it generally comprises in this case from 1 wt% to 15 wt% of said oil-in-water emulsifier system.
  • the inverse latex according to the invention may also contain various additives such as complexing agents or chain-limiting agents.
  • the subject of the invention is an inverse latex as defined above comprising from 15% to 60% by weight, and preferably from 25% to 40% by weight, of said cationic polyelectrolyte.
  • the subject of the invention is an inverse latex as defined above comprising more than 60% up to 80% by mass, and preferably more than 60% to 70% by mass, of said polyelectrolyte. cationic.
  • the subject of the invention is a process for preparing the inverse latex as defined above, comprising the following steps:
  • step b) during which the polymerization reaction is initiated by introduction into the emulsion formed at the end of step a), a free radical initiator and optionally a co-initiator and then left unrolling to obtain said inverse latex.
  • the polymerization reaction is generally initiated by a hydrogen sulfite ion-generating oxidoreduction pair (HSO 3 ) such as the cumene hydroperoxide-sodium metabisulphite pair (Na 2 S 2 0 5 ) or the tertobutyl hydroperoxide-sodium metabisulphite pair at a temperature of less than or equal to 10 ° C., if desired accompanied by a co-initiator polymerization agent such as, for example, azobis (isobutyronitrile), dilauroylperoxide or sodium persulfate and then conducted almost adiabatically to a temperature greater than or equal to 50 ° C, or by controlling the
  • the process as defined above further comprises a step c), during which said oil-in-water emulsifier system is added to the inverse latex formed at the end of step b) , to obtain a self-invertible inverse latex.
  • step c) of the process as defined above the addition of said emulsifier system of oil-in-water type, the addition is generally at a temperature of less than or equal to 50 ° C.
  • the process as defined above further comprises a step b, in which the inverse latex resulting from step b) is concentrated to obtain a concentrated inverse latex, before the implementation. if necessary, of step c).
  • the process as defined above further comprises a step C _, during which the self-invertible inverse latex from step c) is concentrated, to obtain a self-invertible inverse latex. concentrated.
  • the concentration of the medium is generally carried out by distillation until the desired content of cationic polyelectrolyte is reached within the composition that is the subject of the present invention.
  • the process as defined above further comprises a step d) during which the inverse latex resulting from step b), the concentrated inverse latex resulting from step b1), the latex self-invertible inverse reverse from step c) or the concentrated autoinversible reverse latex from step c1) is spray-dried to form a powder of said cationic polyelectrolyte.
  • the subject of the invention is also a linear, connected or crosslinked cationic polyelectrolyte powder, characterized in that it is obtained by the process as defined above.
  • the polyelectrolyte which is the subject of the present invention, as well as the inverse latexes and the self-reversing inverse latexes comprising them, are advantageously used as thickeners and / or as emulsifiers in cosmetic or pharmaceutical compositions intended for the care and / or hair conditioning.
  • the subject of the invention is the use of the inverse latex as defined above or of the powder obtained by the process as defined above, as a thickening agent and / or as an emulsifying agent for the compositions. cosmetics or pharmaceuticals and more particularly those intended for the care and / or conditioning of the hair.
  • the powder or the optionally reversing self-inert latex, objects of the present invention can be formulated in cosmetic or pharmaceutical formulas such as foams, gels, lotions, sprays, shampoos, conditioners, hand lotions and the body, sunscreens, and more generally in care products.
  • Such cosmetic or pharmaceutical compositions are usually in the form of emulsion shampoos, microemulsions and especially in the case of conditioners, vaporizable emulsions.
  • the subject of the invention is a cosmetic or pharmaceutical composition characterized in that it contains, as emulsifying and / or thickening agent, an effective amount of inverse latex as defined above or of the powder obtained by the process. as defined above.
  • effective amount is meant a weight proportion of between about 1% and about 10% by weight of the inverse latex as defined above and about 0.2% by weight to about 5% of the powder as defined above.
  • An aqueous phase is prepared by mixing successively:
  • An aqueous phase is prepared by mixing successively:
  • An oil phase is prepared by mixing successively:
  • SIMALINE TM IE 200 block copolymers with a molecular weight between 2500 and 3500
  • inverse latex L1 At the end of the reaction, after a conventional stage devoted to the destruction of the residual monomers, a reverse latex is obtained. 50 g of SIMULSOL TM P7 (the lauryl alcohol heptaethoxylated) are then added with stirring and a latex is obtained. self-invertible inverse (referred to in the following examples as inverse latex L1).
  • AMONYL TM DM 1.00%
  • N-cocoyl amino acids 0.70%
  • Jojoba oil 1, 0%
  • AMONYL TM DM 1, 0%
  • SEPIPERL TM N (cocoyl glucoside 1 cocoyl alcohol) marketed by SEPPIC.
  • AMONYLT M DM (Quatemium 82) marketed by SEPPIC.
  • SEPICAP MP (sodium cocoyl amino acids 1 potassium dimethicone copolyol panthenyl phosphate) marketed by SEPPIC.
  • SIMULSOL TM 1293 is hydrogenated and ethoxylated castor oil, with an ethoxylation index equal to 40, sold by the company SEPPIC.
  • KETROL TM T is xanthan gum marketed by the company KELCO.
  • LANOL TM 99 is isononyl isononanoate sold by the company SEPPIC.
  • DC1501 is a mixture of cyclopentasiloxane and dimethiconol marketed by Dow Chemical.
  • MONTANOV TM 82 is an emulsifier based on cetearyl alcohol and cocoylglucoside.
  • SEPICIDE TM Cl imidazolidine urea
  • SEPPIC preservative
  • SEPICIDE TM HB which is a mixture of phenoxyethanol, methylparaben, ethylparaben, propylparaben and butylparaben, is a preservative marketed by the company SEPPIC.
  • LANOL TM P is a stabilizing additive marketed by the company SEPPIC.

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Abstract

The invention relates to positive latex including a straight, branched, or cross-linked cationic polyelectrolyte from the polymerization, in molar %, of: a molar ratio of greater than or equal to 70% and less than or equal to 99% of monomer units from at least one cationic monomer; b) a non-zero molar ratio of less than 20% of monomer units from N-(2-hydroxyethyl)acrylamide; c) a non-zero molar ratio of less than or equal to 15% of monomer units from at least one monomer of formula (I): A-C(=0)-0-[(CH2-CH(RI)-0]n-R, where n is, independently, a number between 1 and 50, A is an unsaturated aliphatic radical including 2 to 6 carbon atoms, R1 is a hydrogen atom, a methyl radical, or an ethyl radical, and R is a straight or branched, saturated or unsaturated aliphatic radical including 8 to 30 carbon atoms; d) optionally, a molar ratio of greater than 0% and less than or equal to 10% of monomer units from at least one neutral monomer other than said N-(2-hydroxyethyl)acrylamide, it being assumed that said molar ratio is strictly less than that of the monomer units from the N-(2-hydroxyethyl)acrylamide, and optionally, a molar ratio of monomer units from at least one neutral monomer other than said N-(2-hydroxyethyl)acrylamide; and e) optionally, a molar ratio of greater than 0% and less than or equal to 1% of a diethylene or polyethylene cross-linking monomer. The invention also relates to a method for the preparation and use of said positive latex as a thickener for cosmetic or pharmaceutical compositions.

Description

Nouveaux épaississants cationiques, résistants aux électrolytes et utilisables sur une large gamme de pH procédé pour leur préparation et composition en contenant.  New cationic thickeners, resistant to electrolytes and usable over a wide pH range process for their preparation and composition containing.
L'invention a pour objet, de nouveaux épaississants cationiques polymères leur procédé de préparation ainsi que leur utilisation comme agent épaississant et/ou émulsionnant. The invention relates to novel polymeric cationic thickeners their process of preparation as well as their use as thickening and / or emulsifying agent.
L'épaississement des phases aqueuses est en général réalisé en y incorporant des polymères hydrophiles de toutes sortes, qu'ils soient synthétiques ou d'origine naturelle.  The thickening of the aqueous phases is generally carried out by incorporating hydrophilic polymers of all kinds, whether synthetic or of natural origin.
Parmi les polymères d'origine naturelle, les gommes de xanthane ou de guar sont assez largement utilisées. Ils ont cependant les inconvénients classiques des produits naturels, à savoir une qualité et un prix fluctuant. Among polymers of natural origin, xanthan or guar gums are fairly widely used. However, they have the classic disadvantages of natural products, namely a quality and a fluctuating price.
Parmi les épaississants synthétiques hydrophiles les plus largement utilisés, il y a les polymères sous forme de poudres ou de latex inverses auto-inversibles. Ils sont mis en œuvre dans une large gamme de pH et sont souvent bien tolérés par l'homme. De telles compositions sont décrites par exemple dans les brevets américains publiés sous les numéros US 5,004,598, US 6, 197,287, US 6,136,305, US 6,346,239 ou dans la demande brevet européen publiée sous le numéro EP 0 503 853.  Among the most widely used hydrophilic synthetic thickeners are polymers in the form of powders or inverse self-reversing latexes. They are implemented in a wide pH range and are often well tolerated by humans. Such compositions are described, for example, in the US Pat. Nos. 5,004,598, 6,197,287, 6,136,305, 6,346,239 or in the European patent application published under the number EP 0 503 853.
Ces polymères sont anioniques et sont donc essentiellement destinés à épaissir des phases aqueuses contenant les différents constituants classiques que l'on peut trouver dans des formulations topiques de l'industrie cosmétique, dermo-pharmaceutique ou pharmaceutique. On citera notamment des huiles, des tensioactifs (non ioniques ou anioniques) encore appelés émulsionnants, des sels minéraux, des acides faibles.  These polymers are anionic and are therefore essentially intended to thicken aqueous phases containing the various conventional constituents that can be found in topical formulations of the cosmetic, dermopharmaceutical or pharmaceutical industry. These include oils, surfactants (nonionic or anionic) also called emulsifiers, mineral salts, weak acids.
Certaines formulations notamment destinées au soin capillaire contiennent des tensioactifs cationiques et ou des polymères conditionneurs cationiques. Dans ce cas particulier, les épaississants constitués par des polymères anioniques ne sont pas recommandés à cause des interactions électrostatiques entre les charges positives et négatives qui provoquent une précipitation du polymère et on utilise de préférence des polymères épaississants cationiques comme ceux décrits dans les brevets américains publiés sous les numéros US 4,806,345 et US 5, 100,660.  Certain formulations intended in particular for hair care contain cationic surfactants and cationic conditioning polymers. In this particular case, anionic polymer thickeners are not recommended because of the electrostatic interactions between the positive and negative charges that cause precipitation of the polymer, and cationic thickening polymers such as those described in the published US patents are preferably used. under US 4,806,345 and US 5, 100,660.
La demande internationale publiée sous le numéro WO 2005/074868 divulgue une composition pour le traitement des cheveux comprenant un copolymère de 20% à 90% en poids de N-hydroxyalkyl acrylamide et de 10% à 80% en poids d'un monomère cationique.  The international application published under the number WO 2005/074868 discloses a composition for treating hair comprising a copolymer of 20% to 90% by weight of N-hydroxyalkyl acrylamide and 10% to 80% by weight of a cationic monomer.
Bien que ces derniers se comportent de manière satisfaisante en milieu acide et qu'ils soient compatibles avec les tensioactifs cationiques, ils perdent néanmoins de leur pouvoir épaississant dans des formulations riches en électrolytes. Ce problème a été partiellement résolu grâce aux polymères divulgués dans la demande de brevet européen publiée sous le numéro EP 1 149 862. Par contre pour des formulations dont le pH est supérieur à 7,5 on observe au bout de quelques semaines une diminution de la viscosité des phases aqueuses épaissies avec ceux-ci. Although the latter behave satisfactorily in an acid medium and are compatible with cationic surfactants, they nevertheless lose their thickening power in electrolyte-rich formulations. This problem has been partially solved thanks to the polymers disclosed in the European patent application published under the number EP 1 149 862. On the other hand, for formulations whose pH is greater than 7.5, after a few weeks a decrease in viscosity of the aqueous phases thickened therewith.
C'est pourquoi les inventeurs ont cherché à développer des polymères épaississant de type cationique, résistants aux électrolytes et fonctionnant à des pH alcalin allant jusqu'à 10 c'est-à-dire permettant d'obtenir des formules dont les viscosités restent stables plusieurs mois.  This is why the inventors have sought to develop cationic type thickening polymers which are resistant to electrolytes and operate at alkaline pH up to 10, that is to say, to obtain formulas whose viscosities remain stable several times. month.
Selon un premier aspect, l'invention a pour objet un latex inverse comprenant un polyélectrolyte cationique, linéaire, branché ou réticulé, issu de la polymérisation pour 100% molaire :  According to a first aspect, the subject of the invention is an inverse latex comprising a cationic, linear, branched or crosslinked polyelectrolyte resulting from the polymerization for 100 mol%:
a) d'une proportion molaire supérieure ou égale à 70% et inférieure ou égale 99%, d'unités monomériques issues d'au moins un monomère cationique,  a) a molar proportion greater than or equal to 70% and less than or equal to 99%, of monomeric units derived from at least one cationic monomer,
b) d'une proportion molaire non nulle et inférieure à 20%, d'unités monomériques issues du N-(2-hydroxy éthyl) acrylamide,  b) a non-zero and less than 20% molar proportion of monomeric units derived from N- (2-hydroxyethyl) acrylamide,
c) d'une proportion molaire non nulle et inférieure ou égale à 15% d'unités monomériques issues d'au moins un monomère de formule (I) :  c) a non-zero molar proportion and less than or equal to 15% of monomeric units derived from at least one monomer of formula (I):
A-C(=0)-0-[(CH2-CH(R,)-0]n-R (I) AC (= O) -O - [(CH 2 -CH (R,) - O] n -R (I)
dans laquelle n représente indépendamment l'un de l'autre, un nombre compris entre 1 et 50, A représente un radical monovalent aliphatique insaturé comprenant de 2 à 6 atomes de carbone, Ri représente un atome d'hydrogène, un radical méthyle ou un radical éthyle et R représente un radical aliphatique hydrocarboné, linéaire ou ramifié, saturé ou insaturé, comprenant de 8 à 30 atomes de carbone, in which n represents, independently of one another, a number of between 1 and 50, A represents an unsaturated aliphatic monovalent radical comprising from 2 to 6 carbon atoms, R 1 represents a hydrogen atom, a methyl radical or a ethyl radical and R represents a linear or branched, saturated or unsaturated hydrocarbon-based aliphatic radical comprising from 8 to 30 carbon atoms,
d) optionnellement d'une proportion molaire supérieure à 0% et inférieure ou égale à 10% et d'unités monomériques issues d'au moins un monomère neutre différent dudit N-(2- hydroxy éthyl) acrylamide, étant entendu que cette proportion molaire est strictement inférieure à celle des unités monomériques issues du N-(2-hydroxy éthyl) acrylamide, et  d) optionally of a molar proportion greater than 0% and less than or equal to 10% and of monomeric units derived from at least one neutral monomer different from said N- (2-hydroxyethyl) acrylamide, it being understood that this molar proportion is strictly lower than that of monomeric units derived from N- (2-hydroxyethyl) acrylamide, and
e) optionnellement d'une proportion molaire supérieure à 0% et inférieure ou égale à 1 % d'un monomère de réticulation diéthylénique ou polyéthylénique.  e) optionally of a molar proportion greater than 0% and less than or equal to 1% of a diethylenic or polyethylenic crosslinking monomer.
Par latex inverse, on désigne cadre de la présente invention, une émulsion eau -dans - huile du polyélectrolyte tel que défini ci-dessus.  By inverse latex is meant frame of the present invention, a water-in-oil emulsion of the polyelectrolyte as defined above.
Par polyélectrolyte branché, on désigne un polyélectrolyte non linéaire qui possède des chaînes pendantes de manière à obtenir, lorsqu'il est mis en solution dans l'eau, un fort état d'enchevêtrement conduisant à des viscosités, à bas gradient de vitesse, très importantes.  The term "connected polyelectrolyte" denotes a nonlinear polyelectrolyte which has pendant chains so as to obtain, when dissolved in water, a high state of entanglement leading to viscosities with a low rate of gradient, very important.
Par polyélectrolyte réticulé, on désigne un polyélectrolyte non linéaire se présentant à l'état de réseau tridimensionnel insoluble dans l'eau, mais gonflable dans l'eau et conduisant donc à l'obtention d'un gel chimique. Crosslinked polyelectrolyte means a nonlinear polyelectrolyte in the form of a three-dimensional network which is insoluble in water but swellable in water and conducts therefore to obtain a chemical gel.
Dans le latex inverse tel que défini ci-dessus, le système émulsionnant de type "eau dans huile" (E/H) est constitué soit d'un seul tensioactif soit d'un mélange de tensioactifs, à condition que ledit tensioactif ou ledit mélange ait une valeur de HLB suffisamment faible pour induire une émulsion eau dans huile. Il y a par exemple les esters de sorbitan, comme l'oléate de sorbitan, commercialisé par la société SEPPIC sous le nom MONT ANE™ 80, l'isostéarate de sorbitan, commercialisé par la société SEPPIC sous le nom MONTANE™ 70 ou le sesquioléate de sorbitan commercialisé par la société SEPPIC sous le nom MONTANE™ 83. Il y aussi certains esters de sorbitan polyéthoxylés, par exemple le mono-oléate de sorbitan pentaéthoxylé commercialisé par la société SEPPIC sous le nom MONTANOX™ 81 ou l'isostéarate de sorbitan pentaéthoxylé commercialisé sous le nom MONTANOX™ 71 par la société SEPPIC. Il y a encore les polyesters de poids moléculaire compris entre 1000 et 3000, produits de la condensation entre un acide poly(isobutènyl) succinique ou son anhydride et tels que l'HYPERMER™ 2296 commercialisé par la société UNIQEMA ou enfin les copolymères blocks de poids moléculaire compris entre 2500 et 3500, comme l'HYPERMER™ B246 commercialisé par la société UNIQEMA ou le SIMALINE™ IE 200 commercialisé par la société SEPPIC.  In the inverse latex as defined above, the "water-in-oil" emulsifier system (W / O) consists of either a single surfactant or a mixture of surfactants, provided that said surfactant or said mixture has a low enough HLB value to induce a water-in-oil emulsion. There are, for example, sorbitan esters, such as sorbitan oleate, marketed by the company SEPPIC under the name MONT ANE ™ 80, sorbitan isostearate, sold by the company SEPPIC under the name MONTANE ™ 70 or sesquioleate sorbitan marketed by the company SEPPIC under the name MONTANE ™ 83. There are also certain polyethoxylated sorbitan esters, for example the pentaethoxylated sorbitan mono-oleate marketed by the company SEPPIC under the name MONTANOX ™ 81 or pentaethoxylated sorbitan isostearate marketed under the name MONTANOX ™ 71 by the company SEPPIC. There are also the polyesters of molecular weight between 1000 and 3000, products of the condensation between a poly (isobutenyl) succinic acid or its anhydride and such as the HYPERMER ™ 2296 marketed by UNIQEMA or finally the weight block copolymers molecular between 2500 and 3500, such as HYPERMER ™ B246 marketed by the company UNIQEMA or SIMALINE ™ IE 200 marketed by the company SEPPIC.
Le latex inverse tel que défini précédemment comprend généralement entre 0,5% massique et 10% massique dudit système émulsionnant de type "eau dans huile".  The inverse latex as defined above generally comprises between 0.5% by weight and 10% by weight of said "water-in-oil" emulsifier system.
Le latex inverse contient généralement entre 1 % et 50% massique d'eau.  The inverse latex generally contains between 1% and 50% by weight of water.
La phase huile du latex inverse auto-inversible décrit ci-dessus, est constituée :  The oil phase of the self-invertible inverse latex described above consists of:
- Soit par une huile minérale, ou par un mélange d'huile minérales, contenant des hydrocarbures saturés de type paraffine, isoparaffine, cycloparaffine, présentant à température ambiante, une densité entre 0,7 et 0,9 et un point d'ébullition supérieur à 180°C, telle que par exemple, l'ISOPAR™ M ou l'ISOPAR™ L, l'EXXOL™ D 100 S commercialisé par EXXON ou les huiles blanches minérales conformes aux réglementations FDA 21 CFR 172.878 et FR 178.3620(a), telles que le MARCOL™ 52 ou le MARCOL™ 82, également commercialisées par EXXON ;  Or by a mineral oil, or a mixture of mineral oils, containing paraffin-type saturated hydrocarbons, isoparaffin, cycloparaffin, having at room temperature, a density between 0.7 and 0.9 and a higher boiling point; at 180 ° C, such as, for example, ISOPAR ™ M or ISOPAR ™ L, EXXOL ™ D 100 S sold by EXXON or mineral white oils in compliance with FDA 21 CFR 172.878 and FR 178.3620 (a) regulations. such as MARCOL ™ 52 or MARCOL ™ 82, also marketed by EXXON;
Soit par une huile de synthèse, ou par un mélange d'huile de synthèse, telle que les polyisobutènes hydrogéné, notamment ceux commercialisés en France par la société Ets B. Hossow et Cie sous le nom PARLEAM - POLYSYNLANE™ et cité dans Michel and Irène Ash ; Thésaurus of Chemical products, Chemise Publicité Cos, Ince. 1986 Volume I, page 21 1 (ISBN 0 7131 36030) ; les polydécènes ; l'isohexadécane, identifié dans Chemical Abstracts par le numéro RN = 93685 - 80 - 4 et qui est un mélange d'iso paraffines en C12, Ci6 et C2o contenant au moins 97% d'isoparaffimes en Ci6, parmi lesquelles le constituant principal est le 2,2,4,4,6,8,8-heptaméthyl nonane (RN = 4390-04-9), commercialisé en France par la société Bayer ; l'isododécane, commercialisé en France par la société Bayer ; Either by a synthetic oil, or by a mixture of synthetic oil, such as hydrogenated polyisobutenes, especially those marketed in France by the company Ets B. Hossow and Co. under the name PARLEAM-POLYSYNLANE ™ and cited in Michel and Irene Ash; Thesaurus of Chemical products, Advertising Shirt Cos, Ince. 1986 Volume I, page 21 1 (ISBN 0 7131 36030); polydecenes; isohexadecane, identified in Chemical Abstracts by the number RN = 93685-80 - 4 which is a mixture of isoparaffins C12, C 6 and C 2 o containing at least 97% isoparaffimes -C 6, among which the main constituent is 2,2,4,4,6,8,8-heptamethylnonane (RN = 4390-04-9), marketed in France by the company Bayer; isododecane, marketed in France by Bayer;
- Soit par une huile végétale, ou par un mélange d'huiles végétales, telle que le squalane qui est identifié dans Chemical Abstracts par le numéro RN = 1 1 1 -01-3 et qui est un mélange d'hydrocarbures contenant plus de 80% massique de 2,6, 10,15,19,23-hexaméthyl tétracosane ; ou une huile végétale de type ester ou triglycéride, comme le coco caprylate caprate, par exemple le DUB™ 81 OC fourni par la société Dubois, ou encore l'huile de Jojoba ;  - Either by a vegetable oil, or by a mixture of vegetable oils, such as squalane which is identified in Chemical Abstracts by the number RN = 1 1 1 -01-3 and which is a mixture of hydrocarbons containing more than 80 % by weight of 2,6, 10,15,19,23-hexamethyltetracosane; or a vegetable oil of the ester or triglyceride type, such as coco caprylate caprate, for example the DUB ™ 81 OC supplied by the Dubois company, or the jojoba oil;
- Soit par un mélange de plusieurs de ces différentes huiles.  - Or by a mixture of several of these different oils.
Le latex inverse tel que défini précédemment comprend généralement pour 100% massique de 5% à 50% massique d'huile.  The inverse latex as defined above generally comprises, for 100% by weight, from 5% to 50% by weight of oil.
Par monomère cationique, on désigne principalement un monomère aliphatique comportant une fonction ammonium quaternaire et moins une liaison carbone-carbone insaturée. Un tel monomère est généralement disponible sous forme notamment de sels.  By cationic monomer is meant primarily an aliphatic monomer having a quaternary ammonium function and less an unsaturated carbon-carbon bond. Such a monomer is generally available in particular in the form of salts.
Par sels on désigne plus particulièrement les halogénures, tels que les bromures les chlorures ou les iodures desdits monomères à fonction ammonium quaternaire  The term "salts" denotes, more particularly, halides, such as bromides, chlorides or iodides, of said quaternary ammonium-functional monomers.
Selon un aspect particulier, l'invention a pour objet un latex inverse tel que défini précédemment, pour lequel les unités monomériques issues d'au moins un monomère cationique, constitutives dudit polyélectrolyte cationique, sont issues des sels d'ammonium quaternaires suivants :  According to a particular aspect, the subject of the invention is an inverse latex as defined above, for which the monomeric units originating from at least one cationic monomer, constitutive of said cationic polyelectrolyte, are derived from the following quaternary ammonium salts:
- Les sels de Ν,Ν,Ν-triméthyl 3-[(2-méthyl 1-oxo 2-propènyl) amino] propanammonium, - Les sels de Ν,Ν,Ν-triméthyl 3-[(1-oxo 2-propènyl) amino] propanammonium, ou  - Salts of Ν, Ν, Ν-trimethyl 3 - [(2-methyl-1-oxo-2-propenyl) amino] propanammonium, - salts of Ν, Ν, Ν-trimethyl 3 - [(1-oxo-2-propenyl) ) amino] propanammonium, or
- Les sels de diallyl diméthylammonium,  - Diallyl dimethylammonium salts,
et plus particulièrement : and more particularly :
- Le chlorure de Ν,Ν,Ν-triméthyl 3-[(2-méthyl 1-oxo 2-propènyl) amino] propanammonium (MAMPTAC™) ;  Le, Ν, Ν-trimethyl-3 - [(2-methyl-1-oxo-2-propenyl) amino] propanammonium chloride (MAMPTAC ™);
- Le ch loru re de Ν , Ν , Ν-triméthyl 3-[(1-oxo 2-propènyl) amino] propanammonium - The ch, Ν, Ν-trimethyl 3 - [(1-oxo-2-propenyl) amino] propanammonium chloride
(APTAC™) ; ou (APTAC ™); or
- Le chlorure de diallyl diméthylammonium (DADMAC™).  - Diallyl dimethylammonium chloride (DADMAC ™).
Dans la formule (I) telle que définie précédemment, le radical divalent :  In the formula (I) as defined above, the divalent radical:
-[(CH2-CH(R1)-0]n- représente notamment : - [(CH 2 -CH (R 1 ) -O] n - represents in particular:
- Soit une chaîne composée uniquement de groupes éthoxyle (Ri = H ; n >0),  - Let a chain composed only of ethoxyl groups (Ri = H; n> 0),
- Soit une chaîne composée uniquement de groupes propoxyle (Ri = CH3 n > 0),- Let a chain composed only of propoxyl groups (R 1 = CH 3 n> 0),
- Soit une chaîne composée uniquement de groupes butoxyle (Ri = C2H5 ; n> 0),Either a chain consisting solely of butoxyl groups (R 1 = C 2 H 5 ; n> 0),
- Soit une chaîne composée d'au moins deux groupes différents choisis parmi les groupes éthoxyle propoxyle et/ou butoxyle. Lorsque cette chaîne est composée de groupes différents, ils sont distribués tout au long de cette chaîne, de façon séquencée ou aléatoire. - A chain consisting of at least two different groups selected from ethoxyl propoxyl and / or butoxyl groups. When this chain is composed of different groups, they are distributed throughout this chain, sequentially or randomly.
Par monomère neutre différent dudit N-(2-hydroxy éthyl) acrylamide, on désigne des monomère ne comportant aucune fonction acide fort ou faible ni aucun groupe chargé positivement. Ils sont plus particulièrement choisis parmi le vinylpyrrolidone, le diacétoneacrylamide, le Ν,Ν-diméthyl acrylamide, ou l e N-[2-hydroxy-1 , 1-bis(hydroxyméthyl) éthyl] propènamide [ou tris(hydroxyméthyl) acrylamidométhane ou N-[tris(hydroxyméthyl) méthyl] acrylamide dénommé aussi THAM].  By neutral monomer different from said N- (2-hydroxyethyl) acrylamide, there is meant monomers having no strong or weak acid function or positively charged group. They are more particularly chosen from vinylpyrrolidone, diacetoneacrylamide, Ν, Ν-dimethylacrylamide, or N- [2-hydroxy-1,1-bis (hydroxymethyl) ethyl] propenamide [or tris (hydroxymethyl) acrylamidomethane or N- [tris (hydroxymethyl) methyl] acrylamide also called THAM].
Par radical aliphatique, hydrocarboné linéaire, saturé ou insaturé, comprenant de 8 à 30 atomes de carbone, on désigne plus particulièrement pour R, dans la formule (I) telle que définie précédemment :  By linear or saturated or unsaturated aliphatic hydrocarbon radical comprising from 8 to 30 carbon atoms, R denotes more particularly in formula (I) as defined above:
- Soit un radical dérivé des alcools primaires linéaires tels que par exemple, ceux dérivés des alcools octylique, pélargonique, décylique, undécylique, undécénylique, laurique, tridécylique, myristylique, pentadécylique, cétylique, heptadécylique, stéarylique, oléylique, linoléylique, nonadécylique, arachidique, béhènylique, érucylique ou l-triacontanoïque. Il s'agit alors des radicaux octyle, nonyle, décyle, undécyle, 10-undécènyle, dodécyle, tridécyle, tétradécyle, pentadécyle, hexadécyle, heptadécyle, octadécyle, 9-octadécènyle, 10, 12- octadécadiènyle, 13-docosènyle ou triacontanyle ;  - A radical derived from linear primary alcohols such as, for example, those derived from octyl, pelargonic, decylic, undecylic, undecenyl, lauric, tridecyl, myristyl, pentadecyl, cetyl, heptadecyl, stearyl, oleyl, linoleyl, nonadecyl, arachidic alcohols, behenyl, erucylic or l-triacontanoic. These are octyl, nonyl, decyl, undecyl, 10-undecenyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, 9-octadecenyl, 10,12-octadecadienyl, 13-docenyl or triacontanyl radicals;
- Soit un radical dérivé des alcools de Guerbet, qui sont des 1 -alcanols ramifiés répondant à la formule générale :  Or a radical derived from Guerbet alcohols, which are branched 1-alkanols corresponding to the general formula:
CH3-(CH2)p-CH[CH3-(CH2)p.2]-CH2OH, CH 3 - (CH 2 ) p - CH [CH 3 - (CH 2 ) p . 2 ] -CH 2 OH,
dans laquelle p représente un nombre entier compris entre 2 et 14, tels que, par exemple, les radicaux 2-éthyl hexyle, 2-propyl heptyle, 2-butyl octyle, 2-pentyl nonyle, 2-hexyl décyle ou 2- octyl dodécyle ; in which p represents an integer between 2 and 14, such as, for example, the 2-ethyl hexyl, 2-propyl heptyl, 2-butyl octyl, 2-pentyl nonyl, 2-hexyl decyl or 2-octyl dodecyl radicals; ;
- Soit un radical dérivé des isoalcanols répondant à la formule générale :  Or a radical derived from isoalkanols corresponding to the general formula:
CH3-CH(CH3)-(CH2)m-CH2OH, CH 3 -CH (CH 3 ) - (CH 2 ) m -CH 2 OH,
dans laquelle m représente un nombre entier compris entre 2 et 26 tels que, par exemple, les radicaux 4-méthyl pentyle, 5-méthyl hexyle, 6-méthyl heptyle, 15-méthyl pendadécyle ou 16- méthyl heptadécyle ; wherein m represents an integer from 2 to 26 such as, for example, 4-methyl pentyl, 5-methyl hexyl, 6-methyl heptyl, 15-methyl pendadecyl or 16-methyl heptadecyl;
- Soit les radicaux 2-hexyl octyle, 2-octyl décyle ou 2-hexyl dodécyle.  - Let 2-hexyl octyl, 2-octyl decyl or 2-hexyl dodecyl radicals.
Par radical aliphatique hydrocarboné, linéaire ou ramifié, saturé ou insaturé, comprenant de 8 à 30 atomes de carbone, on désigne plus particulièrement pour R; dans la formule (I) telle que définie précédemment, un radical alkyle comportant de 8 à 18 atomes de carbone.  By linear or branched, saturated or unsaturated, hydrocarbon-based aliphatic radical comprising from 8 to 30 carbon atoms, more particularly denotes for R; in the formula (I) as defined above, an alkyl radical containing from 8 to 18 carbon atoms.
Dans la formule (I) telle que définie précédemment, n représente plus particulièrement un nombre compris entre 4 et 25. Dans la formule (I) telle que définie précédemment, A représente plus particulièrement le radical vinyle (CH2=CH-) ou le radical isopropènyle [CH2=C(CH3)-]. In the formula (I) as defined above, n represents more particularly a number between 4 and 25. In the formula (I) as defined above, A represents more particularly the vinyl radical (CH 2 = CH-) or the isopropenyl radical [CH 2 = C (CH 3 ) -].
Selon un aspect particulier de la présente invention, le polyélectrolyte cationique tel que défini ci-dessus est caractérisé en ce que la proportion molaire en unités monomériques issues du ou des monomères cationiques est comprise entre 70% et 95%, plus particulièrement entre 75% et 95%.  According to one particular aspect of the present invention, the cationic polyelectrolyte as defined above is characterized in that the molar proportion of monomeric units originating from the cationic monomer or monomers is between 70% and 95%, more particularly between 75% and 95%.
Selon un autre aspect particulier, l'invention a pour objet un latex inverse tel que défini précédemment, pour lequel lesdites unités monomériques issues d'au moins un monomère cationique, constitutives dudit polyélectrolyte cationique, sont uniquement issues d'un sel de Ν,Ν,Ν-triméthyl 3-[(1-oxo 2-propènyl) amino] propanammonium et notamment du chlorure de Ν,Ν,Ν-triméthyl 3-[(1-oxo 2-propènyl) amino] propanammonium (APTAC™).  According to another particular aspect, the subject of the invention is an inverse latex as defined above, for which said monomeric units originating from at least one cationic monomer, constitutive of said cationic polyelectrolyte, are solely derived from a salt of Ν, Ν , Ν-trimethyl-3 - [(1-oxo-2-propenyl) amino] propanammonium and in particular Ν, Ν, Ν-trimethyl-3 - [(1-oxo-2-propenyl) amino] propanammonium chloride (APTAC ™).
Selon un autre aspect particulier de la présente invention, le polyélectrolyte tel que défini ci-dessus est caractérisé en ce que la proportion molaire en unités monomériques issues du N- (2-hydroxy éthyl) acrylamide est supérieure ou égale à 1 % et inférieure à 20%.  According to another particular aspect of the present invention, the polyelectrolyte as defined above is characterized in that the molar proportion in monomeric units derived from N- (2-hydroxyethyl) acrylamide is greater than or equal to 1% and less than 20%.
Selon un autre aspect particulier de la présente invention, le polyélectrolyte tel que défini ci-dessus est caractérisé en ce que la proportion molaire en unités monomériques issues du composé de formule (I) telle que définie précédemment, est supérieure ou égale à 0,1 % et inférieure ou égale à 15%, plus particulièrement supérieure ou égale à 0,5% et inférieure ou égale à 10%.  According to another particular aspect of the present invention, the polyelectrolyte as defined above is characterized in that the molar proportion in monomeric units derived from the compound of formula (I) as defined above, is greater than or equal to 0.1 % and less than or equal to 15%, more particularly greater than or equal to 0.5% and less than or equal to 10%.
L'invention a plus particulièrement pour objet un latex inverse tel que défini précédemment, dans lequel le polyélectrolyte cationique, linéaire, branché ou réticulé, est issu de la polymérisation pour 100% molaire :  The invention more particularly relates to an inverse latex as defined above, in which the cationic polyelectrolyte, linear, connected or crosslinked, is derived from the polymerization for 100 mol%:
a) d'une proportion molaire supérieure ou égale à 75% et inférieure ou égale 95%, d'unités monomériques issues d'au moins un monomère cationique,  a) of a molar proportion greater than or equal to 75% and less than or equal to 95%, of monomeric units derived from at least one cationic monomer,
b) d'une proportion molaire non nulle et inférieure à 20%, d'unités monomériques issues du N-(2-hydroxy éthyl) acrylamide,  b) a non-zero and less than 20% molar proportion of monomeric units derived from N- (2-hydroxyethyl) acrylamide,
c) d'une proportion molaire supérieure ou égale à 0,5% et inférieure ou égale à 10% d'unités monomériques issues d'au moins un monomère de formule (I) :  c) a molar proportion greater than or equal to 0.5% and less than or equal to 10% of monomeric units derived from at least one monomer of formula (I):
A-C(=0)-0-[(CH2-CH(R,)-0]n-R (I) AC (= O) -O - [(CH 2 -CH (R,) - O] n -R (I)
dans laquelle n représente indépendamment l'un de l'autre, un nombre compris entre 1 et 50, A représente un radical monovalent aliphatique insaturé comprenant de 2 à 6 atomes de carbone, Ri représente un atome d'hydrogène, un radical méthyle ou un radical éthyle et R représente un radical aliphatique hydrocarboné, linéaire ou ramifié, saturé ou insaturé, comprenant de 8 à 30 atomes de carbone, in which n represents, independently of one another, a number of between 1 and 50, A represents an unsaturated aliphatic monovalent radical comprising from 2 to 6 carbon atoms, R 1 represents a hydrogen atom, a methyl radical or a ethyl radical and R represents a linear or branched, saturated or unsaturated hydrocarbon-based aliphatic radical comprising from 8 to 30 carbon atoms,
d) optionnellement d'une proportion molaire supérieure à 0% et inférieure ou égale à 10% et d'unités monomériques issues d'au moins un monomère neutre différent dudit N-(2- hydroxy éthyl) acrylamide, étant entendu que cette proportion molaire est strictement inférieure à celle des unités monomériques issues du N-(2-hydroxy éthyl) acrylamide, et d) optionally with a molar proportion greater than 0% and less than or equal to 10% and of monomeric units derived from at least one neutral monomer different from said N- (2-hydroxyethyl) acrylamide, it being understood that this molar proportion is strictly lower than that of the monomeric units derived from N- (2-hydroxyethyl) ) acrylamide, and
e) optionnellement d'une proportion molaire supérieure ou égale à 0,005% et inférieure ou égale à 1 % d'un monomère de réticulation diéthylénique ou polyéthylénique.  e) optionally of a molar proportion greater than or equal to 0.005% and less than or equal to 1% of a diethylenic or polyethylene crosslinking monomer.
Selon un autre aspect particulier de la présente invention, le polyélectrolyte cationique tel que défini précédemment est réticulé.  According to another particular aspect of the present invention, the cationic polyelectrolyte as defined above is crosslinked.
Dans ce dernier cas l'invention a plus particulièrement pour objet un latex inverse tel que défini ci-dessus, pour lequel ledit monomère de réticulation diéthylénique ou polyéthylénique ou polyélectrolyte est choisi parrmi l'acide diallyloxyacétique ou son sel de sodium ou de potassium, le triallylamine, le triméthylol propanetriacrylate, le diméthacrylate d'éthylèneglycol, le diacrylate de diéthylène glycol , le diallylurée ou le méthylène bis(acrylamide), et tout particulièrement, ledit monomère de réticulation diéthylénique ou polyéthylénique ou polyélectrolyte est le méthylène bis(acrylamide).  In the latter case, the invention more particularly relates to an inverse latex as defined above, for which said diethylenic or polyethylenic or polyelectrolyte crosslinking monomer is chosen from diallyloxyacetic acid or its sodium or potassium salt. triallylamine, trimethylol propanetriacrylate, ethylene glycol dimethacrylate, diethylene glycol diacrylate, diallylurea or methylene bis (acrylamide), and most particularly, said diethylenic or polyethylene crosslinking monomer or polyelectrolyte is methylene bis (acrylamide).
Selon un autre aspect particulier, ledit monomère de réticulation diéthylénique ou polyéthylénique ou polyélectrolyte est mis en œuvre dans la proportion molaire exprimée par rapport aux monomères mis en œuvre, supérieure à 0,05%, plus particulièrement de 0,01 % à 0,2% et tout particulièrement de 0,01 % à 0, 1 %.  According to another particular aspect, said diethylenic or polyethylenic crosslinking monomer or polyelectrolyte is used in the molar proportion, expressed relative to the monomers used, greater than 0.05%, more particularly 0.01% to 0.2%. % and most preferably from 0.01% to 0.1%.
Selon un aspect particulier de la présente invention l'agent réticulant mis en œuvre est le méthylène bis(acrylamide).  According to a particular aspect of the present invention, the crosslinking agent used is methylene bis (acrylamide).
Selon un autre aspect particulier, le composé de formule (I) telle que définie précédemment, est choisi parmi :  According to another particular aspect, the compound of formula (I) as defined above, is chosen from:
- Le méthacrylate de béhènyle pentacosaéthoxylé, composé de formule (I) telle que définie précédemment, dans laquelle R représente le radical docosanyle, A représente le radical isopropènyle, Ri représente un atome d'hydrogène et n est égal à 25.  - The pentacosaethoxylated behenyl methacrylate, compound of formula (I) as defined above, in which R represents the docosanyl radical, A represents the isopropenyl radical, Ri represents a hydrogen atom and n is equal to 25.
- L'acrylate de lauryle tétraéthoxylé, composé qui correspond à la formule (I) telle que définie précédemment, dans laquelle R représente le radical dodécyle, A représente le radical vinyle, Ri représente un atome d'hydrogène et n est égal à 4.  Tetraethoxylated lauryl acrylate, which compound corresponds to the formula (I) as defined above, in which R represents the dodecyl radical, A represents the vinyl radical, R 1 represents a hydrogen atom and n is equal to 4.
Le méthacrylate de stéaryle eicosaéthoxylé, composé de formule (I) telle que définie précédemment, dans laquelle R représente le radical stéaryle, A représente le radical isopropènyle, Ri représente un atome d'hydrogène et n est égal à 20, ou  Eicosaethoxylated stearyl methacrylate, compound of formula (I) as defined above, in which R represents the stearyl radical, A represents the isopropenyl radical, R 1 represents a hydrogen atom and n is equal to 20, or
- Le méthacrylate de lauryle tétraéthoxylé, composé qui correspond à la formule (I) telle que définie précédemment, dans laquelle R représente le radical dodécyle, A représente le radical isopropènyle et n est égal à 4.  Tetraethoxylated lauryl methacrylate, which compound corresponds to formula (I) as defined above, in which R represents the dodecyl radical, A represents the isopropenyl radical and n is equal to 4.
Selon un aspect tout particulier de la présente invention, le latex inverse tel que défini précédemment, est issu de la polymérisation pour 100% molaire : According to a very particular aspect of the present invention, the inverse latex as defined previously, is derived from the polymerization for 100 mol%:
a) d'une proportion molaire supérieure ou égale à 75% et inférieure ou égale 95%, d'unités monomériques issues du chlorure N , N , N-triméthyl 3-[(1-oxo 2-propènyl) amino] propanammonium,  a) of a molar proportion greater than or equal to 75% and less than or equal to 95% of monomeric units derived from N, N, N-trimethyl-3 - [(1-oxo-2-propenyl) amino] propanammonium chloride,
b) d'une proportion molaire non nulle et inférieure à 20%, d'unités monomériques issues du N-(2-hydroxy éthyl) acrylamide,  b) a non-zero and less than 20% molar proportion of monomeric units derived from N- (2-hydroxyethyl) acrylamide,
c) d'une proportion molaire supérieure ou égale à 0,5% et inférieure ou égale à 10% d'unités monomériques issues sont issues du méthacrylate de lauryle tétraéthoxylé,  c) a molar proportion greater than or equal to 0.5% and less than or equal to 10% of monomeric units derived from tetraethoxylated lauryl methacrylate,
et and
e) d'une proportion molaire supérieure ou égale à 0,01% et inférieure ou égale à 0,2% de méthylène bis(acrylamide).  e) a molar proportion greater than or equal to 0.01% and less than or equal to 0.2% of methylene bis (acrylamide).
Selon un autre aspect particulier de la présente invention le latex inverse tel que défini précédemment comprend en outre un système émulsionnant de type "huile-dans eau". According to another particular aspect of the present invention, the inverse latex as defined above further comprises an emulsifier system of the "oil-in-water" type.
Ledit "système émulsionnant du type huile dans eau " (H/E), est constitué soit d'un seul tensioactif soit d'un mélange de tensioactifs, à condition que ledit tensioactif ou ledit mélange ait une valeur de HLB suffisamment élevée pour induire une émulsion huile dans eau. Il ya par exemple : Said "oil-in-water emulsifier system" (O / W) consists of either a single surfactant or a surfactant mixture, provided that said surfactant or mixture has a HLB value high enough to induce oil-in-water emulsion. For example:
- Les esters de sorbitan éthoxylés comme l'oléate de sorbitan polyéthoxylé avec 20 moles d'oxyde d'éthylène commercialisé par la société SEPPIC sous le nom de MONTANOX™ 80 ou le laurate de sorbitan polyéthoxylé avec 20 moles d'oxyde d'éthylène commercialisé par la société SEPPIC sous le nom de MONTANOX™ 20 ;  Ethoxylated sorbitan esters such as polyethoxylated sorbitan oleate with 20 moles of ethylene oxide marketed by the company SEPPIC under the name MONTANOX ™ 80 or polyethoxylated sorbitan laurate with 20 moles of ethylene oxide marketed by the company SEPPIC under the name MONTANOX ™ 20;
- L'huile de ricin polyéthoxylée avec 40 moles d'oxyde d'éthylène commercialisé sous le nom SIMULSOL™ OL50 ;  Castor oil polyethoxylated with 40 moles of ethylene oxide sold under the name SIMULSOL ™ OL50;
- L'alcool oléodécylique décaéthoxylé, commercialisé par la société SEPPIC sous le nom SIMULSOL™ OC 710 ;  Decaethoxylated oleodecyl alcohol, marketed by SEPPIC under the name SIMULSOL ™ OC 710;
- L'alcool laurique heptaéthoxylé commercialisé sous le nom SIMULSOL™ P7 ; ou - Heptaethoxylated lauric alcohol marketed under the name SIMULSOL ™ P7; or
Les hexaoléates de sorbitan polyéthoxylés commercialisés par la société SEPPIC sous le nom SIMALINE IE 400. The polyethoxylated sorbitan hexaoleate sold by the company SEPPIC under the name SIMALINE IE 400.
Lorsqu'il comprend en outre un système émulsionnant de type "huile dans eau", le latex inverse tel que défini précédemment est alors auto-inversible ; il comprend généralement dans ce cas de 1 % massique à 15% massique dudit système émulsionnant de type huile dans eau".  When it further comprises an emulsifier system of "oil-in-water" type, the inverse latex as defined above is then self-invertible; it generally comprises in this case from 1 wt% to 15 wt% of said oil-in-water emulsifier system.
Le latex inverse selon l'invention peut également contenir divers additifs tels que des agents complexants ou des agents limiteurs de chaîne.  The inverse latex according to the invention may also contain various additives such as complexing agents or chain-limiting agents.
Selon un autre aspect particulier de la présente invention, celle-ci a pour objet un latex inverse tel que défini précédemment comprenant de 15% à 60% massique, et de préférence de 25% à 40% massique, dudit polyélectrolyte cationique.  According to another particular aspect of the present invention, the subject of the invention is an inverse latex as defined above comprising from 15% to 60% by weight, and preferably from 25% to 40% by weight, of said cationic polyelectrolyte.
Selon un autre aspect particulier de la présente invention, celle-ci a pour objet un latex inverse tel que défini précédemment comprenant plus de 60% jusqu'à à 80% massique, et de préférence plus de 60% à 70% massique, dudit polyélectrolyte cationique.  According to another particular aspect of the present invention, the subject of the invention is an inverse latex as defined above comprising more than 60% up to 80% by mass, and preferably more than 60% to 70% by mass, of said polyelectrolyte. cationic.
Selon un autre aspect de la présente invention, celle-ci a pour objet un procédé de préparation du latex inverse tel que défini précédemment, comprenant les étapes suivantes : According to another aspect of the present invention, the subject of the invention is a process for preparing the inverse latex as defined above, comprising the following steps:
Une étape a) au cours de laquelle une solution aqueuse comprenant les monomères et les éventuels additifs hydrophiles, est émulsionnée dans une phase huile comprenant les monomères et les éventuels additifs lipophiles en présence dudit système émulsifiant de type eau dans huile ;  A) during which an aqueous solution comprising the monomers and any hydrophilic additives is emulsified in an oil phase comprising the monomers and any lipophilic additives in the presence of said water-in-oil emulsifier system;
Une étape b) au cours de laquelle la réaction de polymérisation est amorcée par introduction dans l'émulsion formée à l'issue de l'étape a), d'un initiateur de radicaux libres et d'éventuellement un co-initiateur puis laissée se dérouler pour obtenir ledit latex inverse. Lors de l'étape b) du procédé tel que défini la réaction de polymérisation est généralement amorcée par un couple oxydoréducteur générateur d'ions hydrogénosulfite (HSO3) tel que le couple hydroperoxyde de cumène - métabisulfite de sodium (Na2S205) ou le couple hydroperoxyde de tertobutyle - métabisulfite de sodium à une température inférieure ou égale à 10°C, si désiré accompagné d'un agent co-initiateur de polymérisation tel que par exemple l'azo-bis(isobutyronitrile), le dilauroylperoxyde ou le persulfate de sodium puis conduite soit de manière quasi adiabatique jusqu'à une température supérieure ou égale à 50°C, soit en contrôlant la température. A step b) during which the polymerization reaction is initiated by introduction into the emulsion formed at the end of step a), a free radical initiator and optionally a co-initiator and then left unrolling to obtain said inverse latex. During step b) of the process as defined, the polymerization reaction is generally initiated by a hydrogen sulfite ion-generating oxidoreduction pair (HSO 3 ) such as the cumene hydroperoxide-sodium metabisulphite pair (Na 2 S 2 0 5 ) or the tertobutyl hydroperoxide-sodium metabisulphite pair at a temperature of less than or equal to 10 ° C., if desired accompanied by a co-initiator polymerization agent such as, for example, azobis (isobutyronitrile), dilauroylperoxide or sodium persulfate and then conducted almost adiabatically to a temperature greater than or equal to 50 ° C, or by controlling the temperature.
Selon un aspect particulier, le procédé tel que défini ci-dessus, comprend en outre une étape c), au cours de laquelle ledit système émulsionnant de type huile dans eau est ajouté au latex inverse formé à l'issue de l'étape b), pour obtenir un latex inverse auto-inversible.  According to a particular aspect, the process as defined above, further comprises a step c), during which said oil-in-water emulsifier system is added to the inverse latex formed at the end of step b) , to obtain a self-invertible inverse latex.
Lors de l'étape c) du procédé tel que défini ci-dessus, l'ajout dudit système émulsionnant de type huile dans eau, l'ajout se fait généralement à une température inférieure ou égale à 50°C.  In step c) of the process as defined above, the addition of said emulsifier system of oil-in-water type, the addition is generally at a temperature of less than or equal to 50 ° C.
Selon un aspect particulier, le procédé tel que défini ci-dessus, comprend en outre une étape b _, au cours de laquelle le latex inverse issu de l'étape b) est concentré pour obtenir un latex inverse concentré, avant la mise en œuvre le cas échéant, de l'étape c). Selon un aspect particulier, le procédé tel que défini ci-dessus, comprend en outre une étape C _, au cours de laquelle le latex inverse auto-inversible issu de l'étape c) est concentré, pour obtenir un latex inverse auto-inversible concentré.  According to a particular aspect, the process as defined above further comprises a step b, in which the inverse latex resulting from step b) is concentrated to obtain a concentrated inverse latex, before the implementation. if necessary, of step c). According to a particular aspect, the process as defined above further comprises a step C _, during which the self-invertible inverse latex from step c) is concentrated, to obtain a self-invertible inverse latex. concentrated.
Lors de l'étape bi ou de l'étape d du procédé tel que défini ci-dessus, la concentration du milieu est généralement réalisé par distillation jusqu'à atteindre la teneur souhaitée en polyélectrolyte cationique au sein de la composition objet de la présente invention.  During step b or step d of the process as defined above, the concentration of the medium is generally carried out by distillation until the desired content of cationic polyelectrolyte is reached within the composition that is the subject of the present invention. .
Selon un aspect particulier, le procédé tel que défini ci-dessus, comprend en outre une étape d) au cours de laquelle le latex inverse issu de l'étape b), le latex inverse concentré issu de l'étape b1 ), le latex inverse auto-inversible issu de l'étape c) ou le latex inverse autoinversible concentré issu de l'étape c1 ), est séché par atomisation, pour former une poudre dudit polyélectrolyte cationique.  According to a particular aspect, the process as defined above further comprises a step d) during which the inverse latex resulting from step b), the concentrated inverse latex resulting from step b1), the latex self-invertible inverse reverse from step c) or the concentrated autoinversible reverse latex from step c1) is spray-dried to form a powder of said cationic polyelectrolyte.
L'invention a aussi pour objet une poudre du polyélectrolyte cationique linéaire, branché ou réticulé caractérisée en ce qu'elle est obtenue par le procédé tel que défini précédemment.  The subject of the invention is also a linear, connected or crosslinked cationic polyelectrolyte powder, characterized in that it is obtained by the process as defined above.
Grâce à son caractère cationique, le polyélectrolyte objet de la présente invention ainsi que les latex inverses et les latex inverses auto-inversibles en comportant, sont avantageusement utilisés comme épaississants et/ou comme émulsionnant dans des compositions cosmétiques ou pharmaceutiques destinées au soin et/ou au conditionnement des cheveux. C'est pourquoi selon un autre aspect, l'invention a pour objet, l'utilisation du latex inverse tel que défini précédemment ou de la poudre obtenue par le procédé tel que défini précédemment, comme agent épaississant et/ou comme agent émulsionnant des compositions cosmétiques ou pharmaceutiques et plus particulièrement celles destinées au soin et/ou au conditionnement des cheveux. Owing to its cationic nature, the polyelectrolyte which is the subject of the present invention, as well as the inverse latexes and the self-reversing inverse latexes comprising them, are advantageously used as thickeners and / or as emulsifiers in cosmetic or pharmaceutical compositions intended for the care and / or hair conditioning. This is why according to another aspect, the subject of the invention is the use of the inverse latex as defined above or of the powder obtained by the process as defined above, as a thickening agent and / or as an emulsifying agent for the compositions. cosmetics or pharmaceuticals and more particularly those intended for the care and / or conditioning of the hair.
La poudre ou le latex inverse éventuellement auto-inversible, objets de la présente invention peuvent être formulés dans des formules cosmétiques ou pharmaceutiques comme des mousses, des gels, des lotions, des sprays, des shampoings, des conditionneurs, des lotions pour les mains et le corps, des écrans solaires, et plus généralement dans des produits de soin.  The powder or the optionally reversing self-inert latex, objects of the present invention can be formulated in cosmetic or pharmaceutical formulas such as foams, gels, lotions, sprays, shampoos, conditioners, hand lotions and the body, sunscreens, and more generally in care products.
Dans le cas du traitement ou de l'entretien du cheveu, de telles compositions cosmétiques ou pharmaceutiques se présentent habituellement sous forme de shampoings d'émulsions, de microémulsions et notamment dans le cas des conditionneurs, d'émulsions vaporisables.  In the case of treatment or maintenance of the hair, such cosmetic or pharmaceutical compositions are usually in the form of emulsion shampoos, microemulsions and especially in the case of conditioners, vaporizable emulsions.
Selon un dernier aspect l'invention a pour objet, une composition cosmétique ou pharmaceutique caractérisée en en ce qu'elle contient comme agent émulsionnant et/ou épaississant, une quantité efficace de latex inverse tel que défini précédemment ou de la poudre obtenue par le procédé tel que défini précédemment.  According to a last aspect, the subject of the invention is a cosmetic or pharmaceutical composition characterized in that it contains, as emulsifying and / or thickening agent, an effective amount of inverse latex as defined above or of the powder obtained by the process. as defined above.
Par quantité efficace, on entend une proportion pondérale comprise entre environ 1 % et environ 10% en poids du latex inverse tel que défini précédemment et environ 0,2% massique à environ 5% de la poudre telle que définie précédemment.  By effective amount is meant a weight proportion of between about 1% and about 10% by weight of the inverse latex as defined above and about 0.2% by weight to about 5% of the powder as defined above.
Les exemples suivants illustrent la présente invention sans toutefois la limiter. The following examples illustrate the present invention without limiting it.
Al - Exemples de préparation de latex inverses ou de poudres selon l'invention Al - Examples of preparation of inverse latexes or powders according to the invention
Exemple 1 : Préparation d'une poudre (Poudre P1) Example 1 Preparation of a Powder (Powder P1)
Préparation de la poudre Preparation of the powder
a) Une phase aqueuse est préparée en mélangeant successivement : a) An aqueous phase is prepared by mixing successively:
- 25,3 g de N-(2-hydroxy éthyl) acrylamide ;  25.3 g of N- (2-hydroxyethyl) acrylamide;
- 242,4g d'une solution commerciale à 75% de chlorure de Ν,Ν,Ν-triméthyl 3-[(1-oxo 2- propènyl) amino] propanammonium (APTAC) ;  242.4 g of a 75% commercial solution of Ν, Ν, Ν-trimethyl-3 - [(1-oxo-propenyl) amino] propanammonium chloride (APTAC);
- 0,066g de méthylène bis(acrylamide) ;  0.066 g of methylene bis (acrylamide);
- 0,27g d ' u ne solution commerciale à 40% du sel de sodium de l'acide triaminepentaacétique ;  0.27 g of a commercial solution containing 40% of the sodium salt of triaminepentaacetic acid;
- Environ 2, 1g d'une solution aqueuse normale d'acide chlorhydrique, de manière à amener le pH à 5 ; et  Approximately 2.1 g of a normal aqueous solution of hydrochloric acid, so as to bring the pH to 5; and
- De l'eau permutée de manière à compléter la masse totale de la phase aqueuse à 325,5g.  - Water permuted so as to complete the total mass of the aqueous phase at 325.5g.
b) On prépare une phase huile est constituée en mélangeant successivement : b) An oil phase is prepared by mixing successively:
- 129,6g d'ISOPAR™ M (isoparaffine C13-C14) ;  129.6 g of ISOPAR ™ M (isoparaffin C13-C14);
- 12,5g MONTANE™ 70 (isostéarate de sorbitan) ;  - 12.5g MONTANE ™ 70 (sorbitan isostearate);
- 4,3g de méthacrylate de lauryle tétraéthoxylé ;  4.3 g of tetraethoxylated lauryl methacrylate;
- 0,04g d'azo-bis(isobutyronitrile).  0.04 g of azobis (isobutyronitrile).
c) Les deux phases sont ensuite intimement mélangées au moyen d'une turbine type ULTRA TURRAX™ pour former une émulsion eau-dans huile. c) The two phases are then intimately mixed using an ULTRA TURRAX ™ type turbine to form a water-in-oil emulsion.
d) L'émulsion obtenue est refroidie jusqu'à environ 10°C et placé sous barbotage d'azote pendant environ 60 minutes. La polymérisation est alors initiée en y incorporant un couple oxydo-réducteur constitué de : d) The resulting emulsion is cooled to about 10 ° C and sparged with nitrogen for about 60 minutes. The polymerization is then initiated by incorporating an oxido-reducing torque consisting of:
8g d'une solution d'hydroperoxyde de cumène constituée (0,043g dans 20 ml d'eau), et 20g d'une solution aqueuse contenant 0,042g de métabisulfite de sodium.  8 g of a cumene hydroperoxide solution (0.043 g in 20 ml of water) and 20 g of an aqueous solution containing 0.042 g of sodium metabisulphite.
e) En fin de réaction, on obtient après une étape classique consacrée à la destruction des monomères résiduels un latex inverse, que l'on sèche par atomisation. on obtient ainsi la poudre de polyélectrolyte cationique attendue (poudre P1 ) Analyse viscosimétrique de la poudre e) At the end of the reaction, after a conventional step devoted to the destruction of the residual monomers, an inverse latex is obtained, which is spray-dried. the expected cationic polyelectrolyte powder (powder P1) is thus obtained Viscosimetric analysis of the powder
Viscosité d'une dispersion aqueuse comprenant 1 ,24% massique de la poudre obtenue : 100 000 mPa.s (Brookfield RVT, M6 V5) Viscosity of an aqueous dispersion comprising 1.24% by weight of the powder obtained: 100,000 mPa.s (Brookfield RVT, M6 V5)
Viscosité d'une dispersion aqueuse comprenant 1 ,24% massique de la poudre obtenue et 0, 1 % massique de chlorure de sodium : 15 OOOmPas (Brookfield RVT, M6 V5) Viscosity of an aqueous dispersion comprising 1.24% by weight of the powder obtained and 0.1% by weight of sodium chloride: 15,000 mPas (Brookfield RVT, M6 V5)
On constate que cette valeur est identique à pH 6, 8 ou à pH10 et qu'elle reste constante après trois mois de stockage à température ambiante. It is found that this value is identical to pH 6, 8 or pH 10 and remains constant after three months of storage at room temperature.
Exemple 2 : Préparation d'un latex inverse auto-inversible selon l'invention Example 2 Preparation of a Self-Invertible Reverse Latex According to the Invention
(Latex inverse L1 ) (Reverse latex L1)
Préparation du latex inverse auto-inversible Preparation of the self-invertible inverse latex
a) Une phase aqueuse est préparée en mélangeant successivement : a) An aqueous phase is prepared by mixing successively:
- 50,6g de N-(2-hydroxy éthyl) acrylamide ;  50.6 g of N- (2-hydroxyethyl) acrylamide;
- 485g d'une solution commerciale à 75% de chlorure Ν,Ν,Ν-triméthyl 3-[(1-oxo 2- propènyl) amino] propanammonium (APTAC) ;  485 g of a 75% commercial solution of Ν, Ν, Ν-trimethyl-3 - [(1-oxo-propenyl) amino] propanammonium chloride (APTAC);
- 0, 13g de méthylène bis(acrylamide) ;  - 0.13 g of methylene bis (acrylamide);
- 0,54g d'une solution commerciale à 40% du sel de sodium de l'acide triaminepentaacétique ;  0.54 g of a commercial solution containing 40% of the sodium salt of triaminepentaacetic acid;
- Environ 4g d'une solution aqueuse normale d'acide chlorhydrique 1 N de manière à amener le pH à 5 ; et  Approximately 4 g of a normal aqueous solution of 1 N hydrochloric acid so as to bring the pH to 5; and
- De l'eau permutée de manière à amener la masse totale de la phase aqueuse à 651g. b) On prépare une phase huile est constituée en mélangeant successivement :  - Water permuted so as to bring the total mass of the aqueous phase to 651g. b) An oil phase is prepared by mixing successively:
- 257g d'isohexadécane  - 257g of isohexadecane
- 16g de MONTANE™ 70 (isostéarate de sorbitan)  - 16g of MONTANE ™ 70 (sorbitan isostearate)
- 10g de SIMALINE™ IE 200 (copolymères blocks de poids moléculaire compris entre 2500 et 3500) ;  10 g of SIMALINE ™ IE 200 (block copolymers with a molecular weight between 2500 and 3500);
- 8,6g de méthacrylate de lauryle tétraéthoxylé ;  - 8.6 g of lauryl methacrylate tetraethoxylated;
- 0,08g d'azo-bis(isobutyronitrile).  0.08 g of azobis (isobutyronitrile).
c) Les deux phases sont ensuite intimement mélangées au moyen d'une turbine type ULTRA TURRAX™ pour former une émulsion eau-dans huile. d) L'ensemble est alors refroidi jusqu'à environ 10°C et placé sous barbotage d'azote pendant environ 60 minutes. La polymérisation est alors initiée en y incorporant un couple oxydo- réducteur constitué de : c) The two phases are then intimately mixed using an ULTRA TURRAX ™ type turbine to form a water-in-oil emulsion. d) The whole is then cooled to about 10 ° C and sparged with nitrogen for about 60 minutes. The polymerization is then initiated by incorporating a redox couple consisting of:
8g d'une solution d'hydroperoxyde de cumène constituée (0,043g dans 20 ml d'eau), et 20g d'une solution aqueuse contenant 0,042g de métabisulfite de sodium.  8 g of a cumene hydroperoxide solution (0.043 g in 20 ml of water) and 20 g of an aqueous solution containing 0.042 g of sodium metabisulphite.
e) En fin de réaction, on obtient après une étape classique consacrée à la destruction des monomères résiduels un latex inverse, On y ensuite ajoute sous agitation, 50g de SIMULSOL™ P7 (L'alcool laurique heptaéthoxylé) et l'on obtient un latex inverse auto-inversible (dénommé dans les exemples suivants latex inverse L1 ). e) At the end of the reaction, after a conventional stage devoted to the destruction of the residual monomers, a reverse latex is obtained. 50 g of SIMULSOL ™ P7 (the lauryl alcohol heptaethoxylated) are then added with stirring and a latex is obtained. self-invertible inverse (referred to in the following examples as inverse latex L1).
Analyse viscosimétrique du latex inverse auto-inversible Viscosimetric analysis of self-invertible inverse latex
Viscosité à 3% dans l'eau à pH = 6 du latex inverse auto-inversible : Viscosity at 3% in water at pH = 6 of the self-invertible inverse latex:
140 000 mPa.s (Brookfield RVT, M5; V5). 140,000 mPa.s (Brookfield RVT, M5, V5).
Viscosité à 3% dans l'eau contenant 0,1 % de chlorure de sodium du latex inverse autoinversible: 14 000 mPa.s (Brookfield RVT, M5; V5) 3% Viscosity in Water Containing 0.1% Sodium Chloride of the Invertable Reverse Latex: 14000 mPa.s (Brookfield RVT, M5, V5)
On constate de plus, que pour ce latex inverse du copolymére d'APTAC/ N-(2-hydroxy éthyl) acrylamide, et contrairement à ce que se passe pour les latex inverses auto-inversibles du copolymére APTAC/acrylamide, la viscosité reste identique à pH 6, 8 ou à pH10 et qu'elle reste constante après trois mois de stockage à température ambiante. It is furthermore noted that for this inverse latex of the APTAC / N- (2-hydroxyethyl) acrylamide copolymer, and contrary to what happens with the inverse self-reversing latexes of the APTAC / acrylamide copolymer, the viscosity remains the same. pH 6, 8 or pH10 and remains constant after three months of storage at room temperature.
Bl - Exemples de formulations. Exemple 3 : Soin antistress pour cheveux Bl - Examples of formulations. Example 3: Anti-stress treatment for hair
Formule  Formula
Phase A Phase A
Eau : QSP 100% Water: 100% QSP
Gomme xanthane 0,50%  Xanthan gum 0.50%
Phase B Phase B
SEPICAP™ MP: 3,00%  SEPICAP ™ MP: 3.00%
Phase C Phase C
Latex inverse L1 : 4,00%  L1 inverse latex: 4.00%
Phase D Phase D
Butylène Glycol : 5,00% LANOL™ 99 : 5,00% Butylene Glycol: 5.00% LANOL ™ 99: 5.00%
SEPICIDE™ HB : 0,30% SEPICIDE ™ HB: 0.30%
SEPICIDE™ CI : 0,20% SEPICIDE ™ CI: 0.20%
Parfum 0,20% Perfume 0,20%
Mode Opératoire Operating mode
Disperser la gomme xanthane dans l'eau avec une défloculeuse. Ajouter ensuite SEPICAP™ MP, puis la composition de l'exemple 1 ; la disperser puis ajouter les ingrédients de la phase D.  Disperse the xanthan gum in the water with a deflocculator. Then add SEPICAP ™ MP, then the composition of Example 1; disperse it then add the ingredients of phase D.
Exemple 4 : Masque crème restructurant pour cheveux stressés et fragilisés Example 4 Restructuring cream mask for stressed and weakened hair
Formule Formula
Phase A Phase A
MONTANOV™ 82 : 3,00%  MONTANOV ™ 82: 3.00%
LANOL™ P : 6,00% LANOL ™ P: 6.00%
AMONYL™ DM : 1 ,00% AMONYL ™ DM: 1.00%
Isononanoate d'isostéaryle : 5,00% Isostearyl Isononanoate: 5.00%
Poudre P1 : 2,50% P1 powder: 2.50%
Phase B Phase B
Eau : QSP 100%  Water: 100% QSP
Phase C Phase C
SEPICAP™ MP : 3,00% SEPICAP ™ MP: 3.00%
SEPICIDE™ HB : 0,30% SEPICIDE ™ HB: 0.30%
SEPICIDE™ Cl : 0, 20% SEPICIDE ™ Cl: 0, 20%
Mode Opératoire  Operating mode
Fondre la phase A à 75°C. Chauffer la phase B à 75°C. Emulsionner A dans B. Vers 40°C introduire les constituants de la phase C.  Melt phase A at 75 ° C. Heat phase B to 75 ° C. Emulsify A in B. At about 40 ° C. introduce the components of phase C.
Exemple 5 : Gel purifiant pour visage Example 5 Purifying gel for face
Formule  Formula
Phase A Phase A
MONTALINE™C 40 : 7,00% MONTALINE ™ C 40: 7.00%
Base nacrante 2078 : 5,00%  Pearl base 2078: 5.00%
Latex inverse L1 : 2,00%  L1 reverse latex: 2.00%
Phase B Phase B
Eau : QSP 100% Exemple 6 : Shampoinq colorant Water: 100% QSP Example 6: Shampoinq dye
Formule  Formula
Phase A  Phase A
MONTALINE™ C 40 : 15,00%  MONTALINE ™ C 40: 15.00%
Cocamphoacétate disodé : 5,00%  Cocamphoacetate disodium: 5.00%
Cetrimonium chloride : 1 ,00%  Cetrimonium chloride: 1.00%
SEPIPERL™ N : 3,00%  SEPIPERL ™ N: 3.00%
Latex inverse L1 : 3,00%  L1 inverse latex: 3.00%
Phase B  Phase B
Couleur QSP  Color QSP
Eau QSP 100%  Water QSP 100%
Exemple 7 : Emulsion fluide à pH alcalin EXAMPLE 7 Fluid Emulsion with Alkaline pH
MARCOL™ 82 : 5,0%  MARCOL ™ 82: 5.0%
Hydroxyde sodium : 10,0%  Sodium hydroxide: 10.0%
Eau : q.s.p. 100%  Water: q.s. 100%
Poudre P1 : 1 ,5%  P1 powder: 1, 5%
Exemple 8 : Masque crème "rince off restructurant pour cheveux stressés et fragilisésEXAMPLE 8 Cream mask "rince off restructuring for stressed and weakened hair
KETROL™T : 0,5% KETROL ™ T: 0.5%
PECOSIL™ SPP50 : 0,75%  PECOSIL ™ SPP50: 0.75%
N-cocoyl aminoacides : 0,70%  N-cocoyl amino acids: 0.70%
Butylèneglycol : 3,0%  Butylene Glycol: 3.0%
Latex inverse L1 : 3,0%  L1 reverse latex: 3.0%
MONTANOV™ 82 : 3,0%  MONTANOV ™ 82: 3.0%
Huile de jojoba : 1 ,0%  Jojoba oil: 1, 0%
LANOL™ P : 6,0%  LANOL ™ P: 6.0%
AMONYL™ DM : 1 ,0%  AMONYL ™ DM: 1, 0%
LANOL™ 99 : 5,0%  LANOL ™ 99: 5.0%
SEPICIDE™ HB : 0,3%  SEPICIDE ™ HB: 0.3%
SEPICIDE™CI : 0,2%  SEPICIDE ™ CI: 0.2%
Parfum : 0,2%  Perfume: 0.2%
Eau : qsp. 100%  Water: qsp. 100%
Exemple 9 : Lotion capillaire Butylène glycol : 3,0% Example 9: Hair Lotion Butylene glycol: 3.0%
Latex inverse L1 : 3,0%  L1 reverse latex: 3.0%
SIMULSOL™1293 : 3,0%  SIMULSOL ™ 1293: 3.0%
Acide lactique : qs. pH = 6  Lactic acid: qs. pH = 6
SEPICIDE™ HB : 0,2%  SEPICIDE ™ HB: 0.2%
SEPICIDE™CI : 0,3%  SEPICIDE ™ CI: 0.3%
Parfum : 0,3%  Perfume: 0.3%
Eau : qs. 100%  Water: qs. 100%
Exemple 10 : Shampooinq protecteur et relaxant Example 10: Protective and Relaxing Shampooinq
Amonyl™ 675 SB : 5,0%  Amonyl ™ 675 SB: 5.0%
Sodium lauroyl éther sulfate à 28% : 35,0%  Sodium lauroyl ether sulfate 28%: 35.0%
Poudre P1 : 3,0%  P1 powder: 3.0%
SEPICIDE™ HB: 0,5%  SEPICIDE ™ HB: 0.5%
SEPICIDE™CI : 0,3%  SEPICIDE ™ CI: 0.3%
Hydroxyde de sodium : q.s. pH = 7,2  Sodium hydroxide: q.s. pH = 7.2
Parfum : 0,3%  Perfume: 0.3%
Colorant (FDC bleu 1/jaune 5) : q.s.  Dye (FDC blue 1 / yellow 5): q.s.
Eau : qsp. 100%  Water: qsp. 100%
Exemple 11 : Protecteur "leave-on" ; Soin antistress pour cheveux Example 11: Protector "leave-on"; Anti-stress treatment for hair
KETROL™T : 0,5%  KETROL ™ T: 0.5%
Mélange de cocoyl aminoacides : 3,0%  Mixture of cocoyl amino acids: 3.0%
Butylèneglycol : 5,0%  Butylene glycol: 5.0%
DC 1501 : 5,0%  DC 1501: 5.0%
Latex inverse L1 : 4,0%  L1 reverse latex: 4.0%
SEPICIDE™ HB: 0,5%  SEPICIDE ™ HB: 0.5%
SEPICIDE™CI : 0,3%  SEPICIDE ™ CI: 0.3%
Parfum : 0,3%  Perfume: 0.3%
Eau : qsp.100  Water: qsp.100
Les définitions des produits commerciaux utilisés dans les exemples sont les suivantes: The definitions of the commercial products used in the examples are as follows:
MONTALINE™ C40 (cocamoniumcarbamoyl chloride) commercialisé par SEPPIC. SEPIPERL™ N : (cocoyl glucoside 1 cocoyl alcohol) commercialisé par SEPPIC. AMONYLTM DM : (Quatemium 82) commercialisé par SEPPIC. SEPICAP MP : (Sodium cocoyl amino acids 1 potassium dimethicone copolyol panthenyl phosphate) commercialisé par SEPPIC. MONTALINE ™ C40 (cocamoniumcarbamoyl chloride) marketed by SEPPIC. SEPIPERL ™ N: (cocoyl glucoside 1 cocoyl alcohol) marketed by SEPPIC. AMONYLT M DM: (Quatemium 82) marketed by SEPPIC. SEPICAP MP: (sodium cocoyl amino acids 1 potassium dimethicone copolyol panthenyl phosphate) marketed by SEPPIC.
SIMULSOL™ 1293 est de l'huile de castor hydrogénée et éthoxylée, avec un indice d'éthoxylation égal à 40, commercialisé par la société SEPPIC.  SIMULSOL ™ 1293 is hydrogenated and ethoxylated castor oil, with an ethoxylation index equal to 40, sold by the company SEPPIC.
KETROL™ T est de la gomme de xanthane commercialisée par la société KELCO. KETROL ™ T is xanthan gum marketed by the company KELCO.
LANOL™ 99 est de l'isononanoate d'isononyle commercialisé par la société SEPPIC. LANOL ™ 99 is isononyl isononanoate sold by the company SEPPIC.
DC1501 est un mélange de cyclopentasiloxane et de diméthiconol commercialisé par la société DOW CHEMICAL. DC1501 is a mixture of cyclopentasiloxane and dimethiconol marketed by Dow Chemical.
MONTANOV™ 82 est un agent émulsionnant à base d'alcool cétéarylique et de cocoylglucoside.  MONTANOV ™ 82 is an emulsifier based on cetearyl alcohol and cocoylglucoside.
Le SEPICIDE™ Cl, imidazolidine urée, est un agent conservateur commercialisé par la société SEPPIC.  SEPICIDE ™ Cl, imidazolidine urea, is a preservative marketed by the company SEPPIC.
Le SEPICIDE™ HB, qui est un mélange de phénoxyéthanol, de méthylparaben, d'éthylparaben, de propylparaben et de butylparaben, est un agent conservateur commercialisé par la société SEPPIC.  SEPICIDE ™ HB, which is a mixture of phenoxyethanol, methylparaben, ethylparaben, propylparaben and butylparaben, is a preservative marketed by the company SEPPIC.
Le LANOL™ P est un additif à effet stabilisant commercialisé par la société SEPPIC.  LANOL ™ P is a stabilizing additive marketed by the company SEPPIC.

Claims

Revendications claims
1. Latex inverse comprenant un polyélectrolyte cationique, linéaire, branché ou réticulé, issu de la polymérisation pour 100% molaire : 1. Reverse latex comprising a linear, branched or crosslinked cationic polyelectrolyte resulting from the polymerization for 100 mol%:
a) d'une proportion molaire supérieure ou égale à 70% et inférieure ou égale 99%, d'unités monomériques issues d'au moins un monomère cationique,  a) a molar proportion greater than or equal to 70% and less than or equal to 99%, of monomeric units derived from at least one cationic monomer,
b) d'une proportion molaire non nulle et inférieure à 20%, d'unités monomériques issues du N-(2-hydroxy éthyl) acrylamide,  b) a non-zero and less than 20% molar proportion of monomeric units derived from N- (2-hydroxyethyl) acrylamide,
c) d'une proportion molaire non nulle et inférieure ou égale à 15% d'unités monomériques issues d'au moins un monomère de formule (I) :  c) a non-zero molar proportion and less than or equal to 15% of monomeric units derived from at least one monomer of formula (I):
A-C(=0)-0-[(CH2-CH(R,)-0]n-R (I) AC (= O) -O - [(CH 2 -CH (R,) - O] n -R (I)
dans laquelle n représente indépendamment l'un de l'autre, un nombre compris entre 1 et 50, A représente un radical monovalent aliphatique insaturé comprenant de 2 à 6 atomes de carbone, Ri représente un atome d'hydrogène, un radical méthyle ou un radical éthyle et R représente un radical aliphatique hydrocarboné, linéaire ou ramifié, saturé ou insaturé, comprenant de 8 à 30 atomes de carbone, in which n represents, independently of one another, a number of between 1 and 50, A represents an unsaturated aliphatic monovalent radical comprising from 2 to 6 carbon atoms, R 1 represents a hydrogen atom, a methyl radical or a ethyl radical and R represents a linear or branched, saturated or unsaturated hydrocarbon-based aliphatic radical comprising from 8 to 30 carbon atoms,
d) optionnellement d'une proportion molaire supérieure à 0% et inférieure ou égale à 10% et d'unités monomériques issues d'au moins un monomère neutre différent dudit N-(2- hydroxy éthyl) acrylamide, étant entendu que cette proportion molaire est strictement inférieure à celle des unités monomériques issues du N-(2-hydroxy éthyl) acrylamide, et  d) optionally of a molar proportion greater than 0% and less than or equal to 10% and of monomeric units derived from at least one neutral monomer different from said N- (2-hydroxyethyl) acrylamide, it being understood that this molar proportion is strictly lower than that of monomeric units derived from N- (2-hydroxyethyl) acrylamide, and
e) optionnellement d'une proportion molaire supérieure à 0% et inférieure ou égale à 1 % d'un monomère de réticulation diéthylénique ou polyéthylénique.  e) optionally of a molar proportion greater than 0% and less than or equal to 1% of a diethylenic or polyethylenic crosslinking monomer.
2. Latex inverse tel que défini à la revendication 1 , pour lequel les unités monomériques issues d'au moins un monomère cationique, constitutives dudit polyélectrolyte cationique, sont issues des sels d'ammonium quaternaires suivants : 2. inverse latex as defined in claim 1, for which the monomeric units derived from at least one cationic monomer, constitutive of said cationic polyelectrolyte, are derived from the following quaternary ammonium salts:
- Les sels de Ν,Ν,Ν-triméthyl 3-[(2-méthyl 1-oxo 2-propènyl) amino] propanammonium, Salts of Ν, Ν, Ν-trimethyl 3 - [(2-methyl-1-oxo-2-propenyl) amino] propanammonium,
- Les sels de Ν,Ν,Ν-triméthyl 3-[(1-oxo 2-propènyl) amino] propanammonium, ou Salts of Ν, Ν, Ν-trimethyl 3 - [(1-oxo-2-propenyl) amino] propanammonium, or
- Les sels de diallyl diméthylammonium.  - Diallyl dimethylammonium salts.
3. Latex inverse tel que défini à l'une des revendications 1 ou 2 pour lequel, dans la formule (I), n représente un nombre compris entre 4 et 25. 3. inverse latex as defined in one of claims 1 or 2 wherein, in the formula (I), n represents a number between 4 and 25.
4. Latex inverse tel que défini à l'une quelconque des revendications 1 à 3 pour lequel, dans la formule (I), A représente le radical vinyle (CH2=CH-) ou le radical isopropènyle [CH2=C(CH3)-] 4. inverse latex as defined in any one of claims 1 to 3 for which, in the formula (I), A represents the vinyl radical (CH 2 = CH-) or the isopropenyl radical [CH 2 = C (CH 3 ) -]
5. Latex inverse tel que défini à l'une quelconque des revendications 1 à 4, pour lequel la proportion molaire en unités monomériques issues du ou des monomères cationiques dans ledit polyélectrolyte cationique, est comprise entre 70% et 95%. 5. inverse latex as defined in any one of claims 1 to 4, wherein the molar proportion of monomeric units derived from the cationic monomer or monomers in said cationic polyelectrolyte, is between 70% and 95%.
6. Latex inverse tel que défini à l'une quelconque des revendications 1 à 5, pour lequel lesdites unités monomériques issues d'au moins un monomère cationique, constitutives dudit polyélectrolyte cationique, sont uniquement issues d'un sel de Ν,Ν,Ν-triméthyl 3-[(1-oxo 2- propènyl) amino] propanammonium et notamment du chlorure de Ν,Ν,Ν-triméthyl 3-[(1-oxo 2- propènyl) amino] propanammonium. 6. inverse latex as defined in any one of claims 1 to 5, wherein said monomeric units derived from at least one cationic monomer, constitutive of said cationic polyelectrolyte, are solely from a salt of Ν, Ν, Ν trimethyl-3 - [(1-oxo-propenyl) amino] propanammonium and in particular Ν, Ν, Ν-trimethyl-3 - [(1-oxo-propenyl) amino] propanammonium chloride.
7. Latex inverse tel que défini à l'une quelconque des revendications 1 à 6, pour lequel la proportion molaire en unités monomériques issues du N-(2-hydroxy éthyl) acrylamide est supérieure ou égale à 1 % et inférieure à 20%. 7. inverse latex as defined in any one of claims 1 to 6, wherein the molar proportion of monomeric units derived from N- (2-hydroxyethyl) acrylamide is greater than or equal to 1% and less than 20%.
8. Latex inverse tel que défini à l'une quelconque des revendications 1 à 7, pour lequel la proportion molaire en unités monomériques issues du composé de formule (I), est supérieure ou égale à 0,1 % et inférieure ou égale à 15%. 8. Reverse latex as defined in any one of claims 1 to 7, wherein the molar proportion of monomeric units derived from the compound of formula (I) is greater than or equal to 0.1% and less than or equal to 15%. %.
9. Latex inverse tel que défini à l'une quelconque des revendications 1 à 8, dans lequel le polyélectrolyte cationique, linéaire, branché ou réticulé, est issu de la polymérisation pour 100% molaire : 9. Reverse latex as defined in any one of claims 1 to 8, wherein the linear cationic polyelectrolyte, connected or crosslinked, is derived from the polymerization for 100 mol%:
a) d'une proportion molaire supérieure ou égale à 75% et inférieure ou égale 95%, d'unités monomériques issues d'au moins un monomère cationique,  a) of a molar proportion greater than or equal to 75% and less than or equal to 95%, of monomeric units derived from at least one cationic monomer,
b) d'une proportion molaire non nulle et inférieure à 20%, d'unités monomériques issues du N-(2-hydroxy éthyl) acrylamide,  b) a non-zero and less than 20% molar proportion of monomeric units derived from N- (2-hydroxyethyl) acrylamide,
c) d'une proportion molaire supérieure ou égale à 0,5% et inférieure ou égale à 10% d'unités monomériques issues d'au moins un monomère de formule (I) :  c) a molar proportion greater than or equal to 0.5% and less than or equal to 10% of monomeric units derived from at least one monomer of formula (I):
A-C(=0)-0-[(CH2-CH(R,)-0]n-R (I) AC (= O) -O - [(CH 2 -CH (R,) - O] n -R (I)
dans laquelle n représente indépendamment l'un de l'autre, un nombre compris entre 1 et 50, A représente un radical monovalent aliphatique insaturé comprenant de 2 à 6 atomes de carbone, Ri représente un atome d'hydrogène, un radical méthyle ou un radical éthyle et R représente un radical aliphatique hydrocarboné, linéaire ou ramifié, saturé ou insaturé, comprenant de 8 à 30 atomes de carbone ; in which n represents, independently of one another, a number of between 1 and 50, A represents an unsaturated aliphatic monovalent radical comprising from 2 to 6 carbon atoms, R 1 represents a hydrogen atom, a methyl radical or a ethyl radical and R represents a linear or branched, saturated or unsaturated hydrocarbon-based aliphatic radical comprising from 8 to 30 carbon atoms;
d) optionnellement d'une proportion molaire supérieure à 0% et inférieure ou égale à 10% et d'unités monomériques issues d'au moins un monomère neutre différent dudit N-(2- hydroxy éthyl) acrylamide, étant entendu que cette proportion molaire est strictement inférieure à celle des unités monomériques issues du N-(2-hydroxy éthyl) acrylamide, et  d) optionally of a molar proportion greater than 0% and less than or equal to 10% and of monomeric units derived from at least one neutral monomer different from said N- (2-hydroxyethyl) acrylamide, it being understood that this molar proportion is strictly lower than that of monomeric units derived from N- (2-hydroxyethyl) acrylamide, and
e) optionnellement d'une proportion molaire supérieure ou égale à 0,005% et inférieure ou égale à 1 % d'un monomère de réticulation diéthylénique ou polyéthylénique.  e) optionally of a molar proportion greater than or equal to 0.005% and less than or equal to 1% of a diethylenic or polyethylene crosslinking monomer.
10. Latex inverse tel que défini à l'une quelconque des revendications 1 à 9, pour lequel le composé de formule (I) telle que définie précédemment, est choisi parmi : 10. Reverse latex as defined in any one of claims 1 to 9, wherein the compound of formula (I) as defined above, is chosen from:
- Le méthacrylate de béhènyle pentacosaéthoxylé ;  - pentacosaethoxylated behenyl methacrylate;
- L'acrylate de lauryle tétraéthoxylé ;  Tetraethoxylated lauryl acrylate;
- Le méthacrylate de stéaryle eicosaéthoxylé ; ou  - Eicosaethoxylated stearyl methacrylate; or
- Le méthacrylate de lauryle tétraéthoxylé.  - Tetraethoxylated lauryl methacrylate.
1 1. Latex inverse tel que défini à la revendication 10, dans laquelle ledit polyélectrolyte cationique est réticulé. 1. The reverse latex as defined in claim 10, wherein said cationic polyelectrolyte is crosslinked.
12. Latex inverse tel que défini à la revendication 1 1 , pour lequel ledit monomère de réticulation diéthylénique ou polyéthylénique ou polyélectrolyte est choisi parmi l'acide diallyloxyacétique ou son sel de sodium ou de potassium, le triallylamine, le triméthylol propanetriacrylate, le diméthacrylate d'éthylèneglycol, le diacrylate de diéthylène glycol, le diallylurée ou le méthylène bis(acrylamide). 12. Inverse latex as defined in claim 1 1, wherein said diethylenic or polyethylene crosslinking monomer or polyelectrolyte is selected from diallyloxyacetic acid or its sodium or potassium salt, triallylamine, trimethylol propanetriacrylate, dimethacrylate d. ethylene glycol, diethylene glycol diacrylate, diallylurea or methylene bis (acrylamide).
13. Latex inverse tel que défini à l'une quelconque des revendications 1 à 12, dans lequel le polyélectrolyte cationique, linéaire, branché ou réticulé, est issu de la polymérisation pour 100% molaire : 13. inverse latex as defined in any one of claims 1 to 12, wherein the linear cationic polyelectrolyte, connected or crosslinked, is derived from the polymerization for 100 mol%:
a) d'une proportion molaire supérieure ou égale à 75% et inférieure ou égale 95%, d'unités m o n o m é ri q u es i ss u es d u ch l o ru re N , N , N-triméthyl 3-[(1-oxo 2-propènyl) amino] propanammonium,  a) with a molar proportion greater than or equal to 75% and less than or equal to 95% of monomeric units of the N, N, N-trimethyl 3 - [(1- oxo 2-propenyl) amino] propanammonium,
b) d'une proportion molaire non nulle et inférieure à 20%, d'unités monomériques issues du N-(2-hydroxy éthyl) acrylamide,  b) a non-zero and less than 20% molar proportion of monomeric units derived from N- (2-hydroxyethyl) acrylamide,
c) d'une proportion molaire supérieure ou égale à 0,5% et inférieure ou égale à 10% d'unités monomériques issues sont issues du méthacrylate de lauryle tétraéthoxylé,  c) a molar proportion greater than or equal to 0.5% and less than or equal to 10% of monomeric units derived from tetraethoxylated lauryl methacrylate,
et e) d'une proportion molaire supérieure ou égale à 0,01 % et inférieure ou égale à 0,2% de méthylène bis(acrylamide). and e) a molar proportion greater than or equal to 0.01% and less than or equal to 0.2% of methylene bis (acrylamide).
14. Latex inverse tel que défini à l'une des revendications 1 à 13, caractérisé en ce qu'il comprend en outre un système émulsionnant de type "huile-dans eau". 14. inverse latex as defined in one of claims 1 to 13, characterized in that it further comprises an emulsifier system of the type "oil-in-water".
15. Procédé de préparation du latex inverse tel que défini à l'une quelconque des revendications 1 à 14, comprenant les étapes suivantes : 15. Process for the preparation of the inverse latex as defined in any one of Claims 1 to 14, comprising the following steps:
Une étape a) au cours de laquelle une solution aqueuse comprenant les monomères et les éventuels additifs hydrophiles, est émulsionnée dans une phase huile comprenant les monomères et les éventuels additifs lipophiles en présence dudit système émulsifiant de type eau dans huile ;  A) during which an aqueous solution comprising the monomers and any hydrophilic additives is emulsified in an oil phase comprising the monomers and any lipophilic additives in the presence of said water-in-oil emulsifier system;
Une étape b) au cours de laquelle la réaction de polymérisation est amorcée par introduction dans l'émulsion formée à l'issue de l'étape a), d'un initiateur de radicaux libres et d'éventuellement un co-initiateur puis laissée se dérouler pour obtenir ledit latex inverse.  A step b) during which the polymerization reaction is initiated by introduction into the emulsion formed at the end of step a), a free radical initiator and optionally a co-initiator and then left unrolling to obtain said inverse latex.
16. Procédé tel que défini à la revendication 15, comprenant en outre une étape c), au cours de laquelle ledit système émulsionnant de type huile dans eau est ajouté au latex inverse formé à l'issue de l'étape b), pour obtenir un latex inverse auto-inversible. The process as defined in claim 15, further comprising a step c), wherein said oil-in-water emulsifier system is added to the inverse latex formed at the end of step b), to obtain a self-invertible inverse latex.
17. Procédé tel que défini à l'une quelconque des revendications 15 ou 16, comprenant en outre une étape b _, au cours de laquelle le latex inverse issu de l'étape b) est concentré, pour obtenir une latex inverse concentré, avant la mise en œuvre le cas échéant, de l'étape c). 18 Procédé tel que défini à la revendication 17, comprenant en outre une étape c-ι, au cours de laquelle le latex inverse auto-inversible issu de l'étape c) est concentré, pour obtenir un latex inverse auto-inversible concentré. 17. A method as defined in any one of claims 15 or 16, further comprising a step b, in which the reverse latex from step b) is concentrated, to obtain a concentrated inverse latex, prior to the implementation, if necessary, of step c). The method as defined in claim 17, further comprising a step c-ι, in which the self-invertible inverse latex from step c) is concentrated, to obtain a concentrated self-invertible inverse latex.
19 Procédé tel que défini à l'une quelconque des revendications 15 à 18, comprenant en outre une étape d) au cours de laquelle le latex inverse issu de l'étape b), le latex inverse concentré issu de l'étape b1 ), le latex inverse auto-inversible issu de l'étape c) ou le latex inverse auto-inversible concentré issu de l'étape c1 ), est séché par atomisation, pour former une poudre dudit polyélectrolyte cationique. 20. Utilisation du latex inverse tel que défini à l'une des revendications 1 à 14 ou de la poudre obtenue par le procédé tel que défini à la revendication 19, comme agent épaississant et/ou comme agent émulsionnant dans des compositions cosmétiques ou pharmaceutiques et plus particulièrement celles destinées au soin et/ou au conditionnement des cheveux. 21. Composition cosmétique ou pharmaceutique caractérisée en en ce qu'elle contient comme agent émulsionnant et/ou épaississant, une quantité efficace du latex inverse tel que défini à l'une des revendications 1 à 14 ou de la poudre obtenue par le procédé tel que défini à la revendication 19. The method as defined in any one of claims 15 to 18, further comprising a step d) during which the inverse latex from step b), the concentrated inverse latex from step b1), the self-invertible inverse latex from step c) or the concentrated self-invertible inverse latex from step c1) is spray-dried to form a powder of said cationic polyelectrolyte. 20. Use of the inverse latex as defined in one of claims 1 to 14 or the powder obtained by the process as defined in claim 19, as a thickening agent and / or as an emulsifying agent in cosmetic or pharmaceutical compositions and more particularly those intended for the care and / or conditioning of the hair. 21. Cosmetic or pharmaceutical composition characterized in that it contains as an emulsifying and / or thickening agent, an effective amount of the inverse latex as defined in one of claims 1 to 14 or the powder obtained by the process such as defined in claim 19.
EP11799790.8A 2010-12-02 2011-11-28 Novel electrolyte-resistant cationic thickeners usable over a wide ph range, method for preparing same, and composition containing same Withdrawn EP2645989A1 (en)

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FR1060038A FR2968308B1 (en) 2010-12-02 2010-12-02 CATIONIC, ELECTROLYTE - RESISTANT AND CURABLE THICKENERS FOR USE ON A BROAD RANGE OF PH PROCESSES FOR THEIR PREPARATION AND COMPOSITION CONTAINING THE SAME.
PCT/FR2011/052789 WO2012072931A1 (en) 2010-12-02 2011-11-28 Novel electrolyte-resistant cationic thickeners usable over a wide ph range, method for preparing same, and composition containing same

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