EP4358933A1 - Copolymerverdickungszusammensetzung mit mindestens einem öl und mindestens einem poly(itaconat) zur verdickung polarer oder apolarer öle - Google Patents

Copolymerverdickungszusammensetzung mit mindestens einem öl und mindestens einem poly(itaconat) zur verdickung polarer oder apolarer öle

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Publication number
EP4358933A1
EP4358933A1 EP22737450.1A EP22737450A EP4358933A1 EP 4358933 A1 EP4358933 A1 EP 4358933A1 EP 22737450 A EP22737450 A EP 22737450A EP 4358933 A1 EP4358933 A1 EP 4358933A1
Authority
EP
European Patent Office
Prior art keywords
radical
formula
equal
representing
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP22737450.1A
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English (en)
French (fr)
Inventor
Miruna BODOC
Estelle ILLOUS
Virginie BARTHE
Georges Manuel Da Costa
Jérôme GUILBOT
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
Original Assignee
Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA
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Application filed by Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA filed Critical Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA
Publication of EP4358933A1 publication Critical patent/EP4358933A1/de
Pending legal-status Critical Current

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Classifications

    • 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
    • A61K8/8164—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 carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers, e.g. poly (methyl vinyl ether-co-maleic anhydride)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/48—Thickener, Thickening system

Definitions

  • Thickening copolymeric composition of polar or apolar oils comprising at least one oil and at least one poly(itaconate)
  • the present invention relates to a copolymeric composition for thickening polar or apolar oils, to its method of manufacture and to topical formulations comprising this thickening composition.
  • the thickening solutions currently proposed have interesting performances, non-negligible advantages in terms of versatility, versatility, but also drawbacks, in particular the impact on the sensory properties of the formula, the formulation conditions.
  • These substances are of different chemical natures: derivatives of silica, clays, polymers of the polyamide type, polyacrylate, polyurethane, beeswax, hydrogenated vegetable oils or even esters or fatty amides of sugars.
  • a solution of the present invention is a thickening copolymeric composition (C) of polar or apolar oils (H2), comprising at least one oil (H1) and at least one poly(itaconate) (P), the at least one poly( itaconate) consisting of:
  • Ri represents an aliphatic hydrocarbon radical, linear or branched, saturated or unsaturated, containing from 6 to 36 carbon atoms and optionally substituted with one or more hydroxyl groups
  • Y or Y' are different and represent the HO— radical, the carboxylic acid function thus present in the formula (Alldl) is in the free acid form or partially or totally salified.
  • Said thickening composition (C) makes it possible to thicken oils (H2) of a polar nature and oils of apolar nature.
  • the term “salified” indicates that the acid function present in a monomer is in an anionic form associated in the form of a salt with a cation, in particular the salts of alkali metals, such as the cations of sodium or potassium, or as nitrogenous base cations such as ammonium salt, lysine salt or the monoethanolamine salt (HOCH2-CH2-NH4 + ). They are preferably sodium or ammonium salts.
  • aliphatic hydrocarbon radical saturated or unsaturated, linear or branched, comprising from 6 to 36 carbon atoms, optionally substituted with one or more hydroxyl groups, is meant for the radical Ri in the formula (Alldl), in the formula (Y6i) and in the formula (llfl') as defined above:
  • Saturated linear alkyl radicals for example n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, n-docosyl;
  • Unsaturated linear radicals such as octenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, docosenyl, 4-dodecenyl or 5-dodecenyl radicals;
  • the saturated or unsaturated, linear or branched aliphatic radicals containing from 6 to 36 carbon atoms substituted by one or two hydroxy groups, such as the hydroxydodecyl, hydroxytetradecyl, hydroxyhexadecyl, hydroxyoctadecyl, hydroxyeicosyl, hydroxydocosyl radicals, for example the 12-hydroxy radical octadecyl.
  • r represents an integer between 2 and 20, for example the radicals isodecyl, isoundecyl, isododecyl, isotridecyl, isotetradecyl, isopentadecyl, isohexadecyl, isopentadecyl, isooctadecyl, isononadecyl, isoeicosyl or isodocosyl;
  • Branched alkyl radicals derived from Guerbet alcohols, of formula (2): CH(CsH2s +i )(C t H2t +i )-CH 2 -OH (2) in which t is an integer between 4 and 18 , s is an integer between 2 and 18 and the sum s + t is greater than or equal to 6, and less than or equal to 22, for example the radicals 2-butyl octyl, 2-butyl decyl, 2-hexyl octyl, 2-hexyl decyl, 2-octyl decyl, 2-hexyl dodecyl, 2-octyl dodecyl, 2-decyl tetradecyl, 2-dodecyl hexadecyl, 2-tetradecyl octadecyl.
  • Ri represents the radical chosen from at least one of the elements of the group consisting of the radicals n-hexyl, n-heptyl , n-octyl, n-nonyl, n- decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, n-eicosyl, n-docosyl, 2-hexyl decyl, 2-octyl decyl, 2-hexyl dodecyl, 2-octyl dodecyl, 2-decyl tetradecyl , 12-hydroxy octadecyl.
  • the poly(itaconate) (P) is a crosslinked poly(itaconate) (P).
  • crosslinked poly(itaconate) (P) denotes the poly(itaconate) as defined above and additionally consisting of at least one monomeric unit derived from a polyethylenic crosslinking monomer (AR).
  • Polyethylenic crosslinking monomer (AR) denotes compounds whose chemical formula includes at least two ethylenic bonds and which make it possible to connect two or more polymer chains during the radical polymerization reaction involving the constituent monomers of the poly(itaconate) such as as described above.
  • the polyethylene crosslinking (AR) monomers can be added to the monomers before the initiation of the radical polymerization process making it possible to prepare the crosslinked poly(itaconate).
  • Polyethylenic crosslinking (RA) monomers can also constitute monomeric compositions involved in the radical polymerization process, as resulting from the esterification between two or more molecules of itaconic acid with one molecule of a polyol.
  • polyol is meant within the meaning of the present invention, an aliphatic molecule substituted by at least two hydroxyl groups.
  • polar oil denotes a hydrophobic compound which comprises in its molecular structure polar groups, namely capable of creating electrostatic interactions with water molecules, of the permanent dipole/permanent dipole type.
  • non-polar oil denotes a hydrophobic compound which cannot create electrostatic interactions with water molecules of the permanent dipole/permanent dipole type.
  • hydrophobic compound denotes a compound which cannot physically interact with water.
  • oil denotes a compound and/or a mixture of hydrophobic compounds, insoluble in water.
  • solution according to the invention may have one or more of the characteristics below:
  • Composition (C) comprises between 20% and 80% by mass, preferably between 40% and
  • the oil (H1) is an oil in liquid form at a temperature between 4°C and 45°C, preferably between 15°C and 45°C and even more preferably at a temperature between 15°C and 35°C;
  • the oil (H1) is a mineral oil or oil of vegetable origin or a mixture of these two types of oils;
  • the mass ratio (P)/(H1) is between 5/1 and 1/5, preferably between 4/1 and 1/4, more preferably between 3/1 and 1/3, even more preferably between 1/2 and 2/1.
  • the mineral oils are preferably chosen from:
  • Paraffins, isoparaffins or cycloparaffins such as: mixtures of alkanes and isoalkanes and cycloalkanes marketed under the names EmogreenTM L15, EmogreenTM L19, EmosmartTM L15, EmosmartTM L19, EmosmartTM V21, IsoparTM L, IsoparTM H, IsoparTM G or IsoparTM M,
  • White mineral oils such as those marketed under the following names: MarcolTM 52, MarcolTM 82, DrakeolTM 6VR, EolaneTM 130, EolaneTM
  • Linear alkanes comprising from 11 to 19 carbon atoms, and more particularly n-undecane, n-dodecane, n-tridecane, and even more particularly the mixture of n-undecane and n-tridecane,
  • Branched alkanes comprising 7 to 20 carbon atoms such as: isododecane, isopentadecane, isohexadecane, isoheptadecane, isooctadecane, isononadecane or isoeicosane, or mixtures of certain between them identified by their INCI name: C7-8 isoparaffin, C8-9 isoparaffin, C9-11 isoparaffin, C9-12 isoparaffin, C9-13 isoparaffin, C9-14 isoparaffin, C9-16 isoparaffin, C10-11 isoparaffin, C10 -12 isoparaffin, C10-13 isoparaffin, Cll-12 isoparaffin, Cll-13 isoparaffin, Cll-14 isoparaffin, C12-14 isoparaffin, C12-20 isoparaffin, C13-14 isoparaffin, C13-16 isoparaffin,
  • Hemi-squalane or 2,6,10-trimethyl-dodecane; CAS number: 3891-98-3
  • squalane or 2,6,10,15,19,23-hexamethyltetracosane
  • hydrogenated polyisobutene or hydrogenated polydecene.
  • the vegetable oils are preferably chosen from oils belonging to the family:
  • R3 represents, independently of R2, a saturated or unsaturated, linear hydrocarbon chain or branched containing from one to twenty-four carbon atoms
  • the compound of formula (IV) representing, for example, methyl laurate, ethyl laurate, propyl laurate, isopropyl laurate, butyl laurate, 2-butyl laurate, hexyl laurate, methyl cocoate, ethyl cocoate, propyl cocoate, isopropyl cocoate, butyl cocoate, 2-butyl cocoate, ethyl cocoate hexyl, octyl cocoate, decyl cocoate, octyl and decyl cocoate, methyl myristate, ethyl myr
  • the compound of formula (IV) represents cocoyl caprylate caprate such as that marketed under the brand name DUB 810C, propyl cocoate, isopropyl cocoate, propyl palmitate, isopropyl palmitate, octyl palmitate.
  • a subject of the present invention is also a formulation for topical use (F) comprising a composition (C) as defined above.
  • the formulation for topical use (F) comprises the mixture of composition (C) and at least one oil (H2).
  • the expression "for topical use” used in the definition of formulation (F) as defined above means that said formulation is prepared to allow its application to the skin, hair, scalp or mucous membranes, whether whether it is a direct application in the case of a cosmetic, dermocosmetic, dermopharmaceutical or pharmaceutical composition or an indirect application, for example in the case of a personal hygiene product in the form of a textile wipe or paper or sanitary products intended to come into contact with the skin or mucous membranes.
  • this formulation for topical use (F) will be a cosmetic formulation.
  • Said formulation for topical use (F) is generally in the form of an oily composition, in the form of a suspension, an emulsion, a microemulsion or a nano-emulsion, whether they are of the water type -in-oil, oil-in-water, water-in-oil-in-water or oil-in-water-in-oil.
  • Said formulation for topical use (F) can be packaged in a bottle, in a pump “bottle” type device, in pressurized form in an aerosol device, in a device provided with an openwork wall such as a grid or in a device provided a ball applicator (called “roll-on”).
  • composition for topical use also comprises excipients and/or active principles usually used in the field of formulations for topical use, in particular cosmetics, dermocosmetics, pharmaceuticals or dermopharmaceuticals, such as thickening surfactants and /or gelling agents, stabilizers, film-forming compounds, hydrotropic agents, plasticizing agents, emulsifying and co-emulsifying agents, opacifying agents, pearlescent agents, superfatting agents, sequestering agents, chelating agents, antioxidants, perfumes, preservatives, conditioning agents, bleaching agents intended for bleaching hair and skin, active ingredients intended to provide a treatment action with respect to the skin or hair, sunscreens, mineral fillers or pigments, particles providing a visual effect or intended for the encapsulation of active ingredients, particles exfoliants, texture agents.
  • cosmetics, dermocosmetics, pharmaceuticals or dermopharmaceuticals such as thickening surfactants and /or gelling agents, stabilizers, film-forming compounds, hydrotropic agents,
  • composition (C) as described above and of an oil (H2) will preferably be carried out at a temperature of between 50°C and 85°C, more preferably at a temperature of 80°C.
  • the homogeneous oily composition obtained is then cooled to room temperature, between 15°C and 30°C.
  • the thickening of the oil (H2) is finally assessed visually by qualifying the consistencies of liquids, viscous or gelled, by measuring a dynamic viscosity value.
  • composition (C) For a composition (C) to be considered effective, the viscous or gelled aspects must at least be achieved.
  • a subject of the present invention is also a method for preparing a thickening copolymer composition (C) according to the invention, comprising: a) producing a composition (C0) of mono- and/or oligoesters of itaconic acid comprising at at least one member of the group consisting of compounds in free acid form or partially or totally salified of formula (Alldl), (llfl) and (llgl) and at least one member of the group consisting of compounds in free acid form or partially or totally salified of formula (liai), (llbl), (I Here), (llcl'), (I lel) and (llhl); b) Preparation of a mixture (Ml) of the composition (C0) produced in step a) with an oil (Hl), c) Copolymerization of the mixture (Ml) initiated by introducing a thermal radical initiator into said mixture (Ml) obtained at the end of step b), and d) Recovery of composition (C).
  • thermal initiator in step c) of the process as defined above, a molecule which, placed at a temperature specific to said structure, generates the production of at least two radicals by homolysis of at least one covalent bond, said radicals making it possible to initiate radical polymerization.
  • the thermal initiator is chosen from the elements of the group consisting of lauroyl peroxide, azo bis (isobutyronitrile) or AIBN, benzoyl peroxide or BPO, azo bis (2-methyl butyronitryl) or AMBN, 4,4'-azo bis (4-cyanovaleric acid) or ACVA, 2,2'-Azobis(2,4-dimethylvaleronitrile, cumene hydroperoxide, di-tert-butyl peroxide or tert -butyl hydroperoxide
  • the process for preparing the thickening composition (C) will preferably comprise one or more of the following characteristics:
  • the method comprises a step of removing at least part of the oil (H1) included in composition (C). This makes it possible to obtain more concentrated compositions (C), the polymerization is carried out at a temperature between 40° C. and 80° C. in step b) a crosslinking monomer (AR) is added.
  • the crosslinking monomer is a diethylenic or polyethylenic crosslinking monomer chosen in particular from ethylene glycol dimethacrylate, diethylene glycol diacrylate, ethylene glycol diacrylate, diallyl urea, triallylamine, trimethylol propanetriacrylate, methylene-bis(acrylamide) .
  • step a) for producing a composition (CO) of mono- and/or oligoesters of itaconic acid comprises the following sub-steps: i) introduction into a reactor of a biobased alcohol or polyol selected from the elements of group consisting of compounds in liquid form:
  • oligoglycerols of the following structure with m representing an integer greater than or equal to 2 and less than or equal to 10, • natural polyols of the following structure: with o representing a number equal to 2 (erythritol), or equal to B (xylitol), or equal to 4 (sorbitol),
  • dehydrated natural polyols of the following structure with X representing a hydrogen atom (erythritan), or else the radical -CH2-OH (xylitan) or else the radical -CH(OH)-CH2-OH (sorbitan),
  • aliphatic fatty alcohols of the following structure: m — o H (Md) with RI representing an aliphatic hydrocarbon radical, linear or branched, saturated or unsaturated, containing from 6 to 36 carbon atoms and optionally substituted with one or more hydroxyl groups,
  • RI represents an aliphatic hydrocarbon radical chosen from n-hexyl, n-heptyl, n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, oleyl, linoleyl radicals , linolenilic, arachidyl, behenyl, erucyl or 12-hydroxystearyl.
  • R'i represents an aliphatic hydrocarbon radical chosen from n-hexyl, n-heptyl, n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, oleyl radicals , linoleylic, linolenilic, arachidylic, behenyl, erucylic or 12-hydroxystearyl. More particularly, the compound of formula (IIf) is batyl alcohol, the structure of which is as follows:
  • polymerization inhibitor denotes, within the meaning of the present invention, compounds which, when added to monomers, rapidly regulate or stop the undesired initiation of a polymerization of said monomers; among these polymerization inhibitors, mention may be made of quinones, hydroquinone, methyl hydroquinone, 1,4-Benzoquinone, 2-tert-Butyl-l,4-benzoquinone, catechols such as for example 4-tert- Butylpyrocatechol-2,6- Di-tert-butylphenol, 6-tert-Butyl-2,4-xylenol, tert-Butylhydroquinone, 4-methoxyphenol, 2,6-Di-tert-butyl-p-cresol, aromatic nitro compounds such as for example nitrobenzenes, nitrophenols, nitrocresols, nitroso compounds, phenothiazine, 1,1-diphenyl-2-picrylhydrazyl, and metal salts
  • sub-steps i) to iii) are carried out at a temperature of between 120 and 180° C.
  • sub-step iii) is carried out at a pressure of between 500 and 20 mbar and, more particularly, between 500 and 200 mbar
  • sub-step iii) has a duration of between 30 minutes and 10 hours.
  • the polymerization inhibitor is chosen from 1,4-Benzoquinone, 2-tert-Butyl-1,4-benzoquinone, Phenothiazine, 6-tert-Butyl-2,4-xylenol, Copper(ll ) Dibutyldithiocarbamate, l,l-Diphenyl-2-picrylhydrazyl, 2,6-Di-tert-Butyl-p-cresol, 4-tert-Butylpyrocatechol-2,6-Di-tert-butylphenol, Hydroquinone, tert-Butylhydroquinone and 4 - methoxyphenol.
  • the esterification catalyst is an acid chosen from sulfuric, hydrochloric, phosphoric, nitric, hypophosphorous, methane- sulfonic acid, para-toluene sulfonic acid, trifluoromethane sulfonic acid ion exchange resins.
  • the molar stoichiometric ratio (IIa)/(I) is greater than or equal to 0.25 and less than or equal to 2.0.
  • the molar stoichiometric ratio (Mb)/(I) is greater than or equal to 0.25 and less than or equal to 2.0.
  • the molar stoichiometric ratio (Ile)/(I) is greater than or equal to 0.25 and less than or equal to 2.0.
  • the molar stoichiometric ratio (lld)/(I) is greater than or equal to 0.25 and less than or equal to 2.0.
  • the molar stoichiometric ratio (Ile)/(I) is greater than or equal to 0.25 and less than or equal to 2.0.
  • the molar stoichiometric ratio (I If) / (I) is greater than or equal to 0.25 and less than or equal to 2.0.
  • the molar stoichiometric ratio (11g)/(I) is greater than or equal to 0.25 and less than or equal to 2.0.
  • compositions of mono- or oligoesters of itaconic acid (A) are characterized by measurements of macroscopic indices (acid and ester indices) and by their content of residual itaconic acid measured by Liquid Phase Chromatography at High Performance (HPLC) coupled to an Ultra-Violet (UV) detector with internal calibration.
  • a conversion rate of itaconic acid is determined.
  • a conversion rate greater than or equal to 75% must be reached in order to consider the proper progress of the esterification reactions.
  • foaming surfactants and/or detergents which can be combined with said thickening composition (C) as defined above in said composition (F), there are foaming surfactants and/or anionic, cationic, amphoteric or not ionic.
  • foaming and/or detergent anionic surfactants which can be combined with said thickening composition (C) as defined above in said composition (F), there are the salts of alkali metals, of alkaline-earth metals, of ammonium, amines, or aminoalcohols, alkylether sulphates, alkyl sulphates, alkylamidoether sulphates, alkylaryl polyether sulphates, monoglyceride sulphates, alpha-olefin sulphonates, paraffin sulphonates, alkyl phosphates, alkyl ether phosphates, alkyl sulfonates, alkylamide sulfonates, alkylaryl sulfonates, alkyl carboxylates, alkyl sulfosuccinates, alkyl ether sulfosuccinates, alkylamide sulfosuccinates, alkyl sulfoacetates, al
  • foaming and/or detergent amphoteric surfactants that can be combined with said thickening composition (C) as defined previously in said composition (F)
  • foaming and/or detergent amphoteric surfactants there are alkylbetaines, alkylamidobetaines, sultaines, alkylamidoalkylsulfobetaines, derivatives imidazolines, phosphobetaines, amphopolyacetates and amphopropionates.
  • foaming and/or detergent cationic surfactants which can be combined with said thickening composition (C) as defined previously in said composition (F), there are in particular quaternary ammonium derivatives.
  • foaming and/or detergent nonionic surfactants which can be combined with said thickening composition (C) as defined previously in said composition (F), there are more particularly alkylpolyglycosides comprising an aliphatic, linear or branched radical, saturated or unsaturated, and comprising from 8 to 16 carbon atoms, such as octyl polyglucoside, decyl polyglucoside, undecylenyl polyglucoside, dodecyl polyglucoside, tetradecyl polyglucoside, hexadecyl polyglucoside, 1-12 dodecanediyl polyglucoside; ethoxylated hydrogenated castor oil derivatives such as the product marketed under the INCI name “Peg-40 hydrogenated castor oil”; polysorbates such as Polysorbate 20, Polysorbate 40, Polysorbate 60, Polysorbate 70, Polysorbate 80, Polysorbate 85; copra amides; N-alkylamines.
  • thickening and/or gelling surfactants which can be combined with said thickening composition (C) as defined above in said composition (F), there are optionally alkoxylated alkylpolyglycoside fatty esters, such as methylpolyglucoside esters ethoxylated such as PEG 120 methyl glucose trioleate and PEG 120 methyl glucose dioleate marketed respectively under the names GLUCAMATETM LT and GLUMATETM DOE120; alkoxylated fatty esters such as PEG 150 pentaerythrytyl tetrastearate marketed under the name CROTHIXTM DS53, PEG 55 propylene glycol oleate marketed under the name ANTILTM 141; polyalkylene glycol carbamates with fatty chains such as PPG-14 laureth isophoryl dicarbamate marketed under the name ELFACOSTM T211, PPG-14 palmeth-60 hexyl dicarbamate marketed under the name ELFAC
  • thickening and/or gelling agents that can be combined with said thickening composition (C) as defined above in said composition (F)
  • thickening and/or gelling agents which can be combined with said thickening composition (C) as defined above in said composition (F)
  • polysaccharides consisting of derivatives of oses, such as sulphated galactans and more particularly carrageenans and agar, uronans and more particularly algins, alginates and pectins, heteropolymers of oses and uronic acids and more particularly xanthan gum, gellan gum, gum arabic exudates and karaya gum, glucosaminoglycans.
  • thickening and/or gelling agents which can be combined with said thickening composition (C) as defined above in said composition (F), there is cellulose, cellulose derivatives such as methyl cellulose, ethyl cellulose, hydroxypropyl cellulose, silicates, starch, hydrophilic derivatives of starch, polyurethanes.
  • stabilizing agents that can be combined with said thickening composition (C) as defined previously in said composition (F)
  • microcrystalline waxes and more particularly ozokerite, mineral salts such as sodium chloride or magnesium chloride, silicone polymers such as polysiloxane polyalkyl polyether copolymers.
  • solvents that can be combined with said thickening composition (C) as defined previously in said composition (F)
  • organic solvents such as glycerol, diglycerol, glycerol oligomers, ethylene glycol, propylene glycol, butylene glycol, 1,3-propanediol, 1,2-propanediol, hexylene glycol, diethylene glycol, xylitol, erythritol, sorbitol, water-soluble alcohols such as ethanol, isopropanol or butanol, mixtures of water and said organic solvents.
  • organic solvents such as glycerol, diglycerol, glycerol oligomers, ethylene glycol, propylene glycol, butylene glycol, 1,3-propanediol, 1,2-propanediol, hexylene glycol, diethylene glycol, xylitol, erythritol, sorbito
  • thermal or mineral waters that can be combined with said thickening composition (C) as defined previously in said composition (F)
  • thermal or mineral waters having a mineralization of at least 300 mg/ l, in particular water from Avène, water from Vittel, water from the Vichy basin, water from Uriage, water from Roche Posay, water from La Bourboule, water from 'Enghien-les-bains, water from Saint-Gervais-les-bains, water from Néris-les-bains, water from Allevard-les-bains, water from Digne, water from Maizieres , water from Neyrac-les-bains, water from Lons le Saunier, water from Rochefort, water from Saint Christau, water from Fumades and water from Tercis-les-bains.
  • hydrotropic agents that can be combined with said thickening composition (C) as defined above in said composition (F)
  • hydrotropic agents there are xylene sulfonates, cumene sulfonates, hexylpolyglucoside, 2-ethylhexylpolyglucoside, n-heptylpolyglucoside.
  • emulsifying surfactants that can be combined with said thickening composition (C) as defined previously in said composition (F)
  • nonionic surfactants anionic surfactants
  • cationic surfactants emulsifying surfactants
  • esters of fatty acids and sorbitol such as the products marketed under MONTAIS appellations!
  • compositions comprising glycerol stearate and ethoxylated stearic acid between 5 moles and 150 moles of ethylene oxide, such as the composition comprising ethoxylated stearic acid at 135 moles of ethylene oxide and glycerol stearate marketed under the name SIMULSOLTM 165; mannitan esters; ethoxylated mannitan esters; sucrose esters; methylglucoside esters; alkylpolyglycosides containing an aliphatic, linear or branched, saturated or unsaturated, and comprising from 14 to 36 carbon atoms, such as tetradecyl polyglucoside, hexadecyl polyglucoside, octadecyl polyglucoside, hexadecyl polyxyloside, octade
  • anionic surfactants which can be combined with said thickening composition (C) as defined previously in said composition (F), there is glyceryl stearate citrate, cetearyl sulphate, soaps such as sodium stearate or stearate of triethanolammonium, N-acylated derivatives of salified amino acids, for example stearoyl glutamate.
  • emulsifying cationic surfactants which can be combined with said thickening composition (C) as defined above in said composition (F), there are the amine oxides, quaternium-82 and the surfactants described in patent application W096 /00719 and mainly those whose fatty chain comprises at least 16 carbon atoms.
  • opacifying and/or pearlescent agents which can be combined with said thickening composition (C) as defined above in said composition (F), there is sodium palmitate, sodium stearate, hydroxystearate sodium, magnesium palmitate, magnesium stearate, magnesium hydroxystearate, ethylene glycol monostearate, ethylene glycol distearate, polyethylene glycol monostearate, polyethylene glycol distearate, fatty alcohols containing 12 to 22 carbon atoms.
  • texture agents that can be combined with said thickening composition (C) as defined previously in said composition (F)
  • N-acylated derivatives of amino acids such as lauroyl lysine marketed under the name AMINOHOPETMLL, octenyl starch succinate marketed under the name DRYFLOTM, myristyl polyglucoside marketed under the name MONTANOVTM 14, cellulose fibers, cotton fibers, chitosan fibers, talc, sericite, mica
  • deodorant agents which can be combined with said thickening composition (C) as defined above in said composition (F)
  • alkali metal silicates zinc salts such as zinc sulphate, zinc gluconate, zinc, zinc chloride, zinc lactate
  • quaternary ammonium salts such as cetyltrimethylammonium salts, cetylpyridinium salts
  • glycerol derivatives such as glycerol caprate, glycerol caprylate, poly
  • waxes that can be combined with said thickening composition (C) as defined above in said composition (F)
  • waxes is meant in the present application compounds and/or mixtures of compounds which are insoluble in water, appearing in a solid appearance at a temperature greater than or equal to 45°C.
  • vitamins and their derivatives in particular their esters, such as retinol (vitamin A) and its esters (eg retinyl palmitate), ascorbic acid (vitamin C) and its esters, sugar derivatives of ascorbic acid (such as ascorbyl glucoside), tocopherol (vitamin E) and its esters (such as tocopherol acetate), vitamins B3 or B10 (niacinamide and its derivatives); compounds showing a lightening or depigmenting action on the skin, such as w-undecelynoyl phenylalanine marketed under the name SEPIWHITETMMSH, SEPICALMTMVG, the mono ester and/or the glycerol diester of w-undecelynoyl phenylalanine, w- undecelynoyl dipeptides, arbutin, koji
  • antioxidant agents that can be combined with said thickening composition (C) as defined previously in said composition (F)
  • EDTA and its salts citric acid, tartaric acid, oxalic acid, BHA (butylhydroxyanisol), BHT (butylhydroxytoluene), tocopherol derivatives such as tocopherol acetate, mixtures of antioxidant compounds such as DISSOLVINE GL 47S marketed by the company Akzo Nobel under the name INCI : Tetrasodium Glutamate Diacetate.
  • sunscreens that can be combined with said thickening composition (C) as defined previously in said composition (F), there are all those appearing in cosmetics directive 76/768/EEC as amended in appendix VII.
  • organic sunscreens that can be combined with said thickening composition (C) as defined above in said composition (F)
  • benzoic acid derivatives such as para-aminobenzoic acids (PABA)
  • PABA para-aminobenzoic acids
  • the monoglycerol esters of PABA the ethyl esters of N,N25 propoxy PABA
  • the ethyl esters of N,N-diethoxy PABA the ethyl esters of N,N-dimethyl PABA
  • anthranilic acid derivatives such as homomenthyl-N-acetyl anthranilate
  • the family of salicylic acid derivatives such as amyl salicylate, homomenthyl salicylate, ethylhexyl salicylate, phenyl salicylate, benzyl salicylate, p-isopropan
  • inorganic sunscreens also called “mineral screens", which can be associated with said thickening composition (C) as defined above in said composition (F), there are titanium oxides, zinc oxides, cerium oxide, zirconium oxide, yellow, red or black iron oxides, chromium oxides.
  • These mineral screens may or may not be micronized, may or may not have undergone surface treatments and may optionally be presented in the form of aqueous or oily pre-dispersions. The invention will now be described in more detail using the examples below.
  • Table 1 The analytical characteristics of all the compositions (A) prepared are collated in Table 1 below.
  • Table 1- Characteristics of the compositions of mono- and/or oligoesters of itaconic acid (A) prepared.
  • esterification conditions as described above make it possible to isolate compositions (A) having ester indices of between 100 and 350 mg KOH/g, testifying to the significant formation of esterified species.
  • the acid numbers are greater than 0, between 60 and 350 mg KOH/g. These values indicate that all the carboxylic acid functions of itaconic acid (I) are not esterified. Finally, the conversion rates calculated from the final mass of composition (A) collected, the percentage of residual itaconic acid (I) contained in this final mass and determined by GPC as well as the mass of itaconic acid (I ) implemented at the start, are systematically greater than 75% indicating satisfactory progress of the esterification reactions.
  • composition (Allf) and 4.3 g of composition (Allh) are dissolved in 28.1 g of DUB 810 C.
  • the solution is homogenized with stirring at approximately 400 rpm at a temperature of 50° C. then subjected to bubbling with nitrogen for 45 min in order to eliminate the oxygen from the medium.
  • the medium is then heated to a temperature of 80°C. 110 mg of lauroyl peroxide are then added to initiate the polymerization reaction. The medium becomes more viscous.
  • After 2 h, 55 mg of lauryl peroxide are then introduced.
  • composition (C1) has a waxy appearance and is heat-conditioned.
  • composition (C2) was isolated.
  • compositions (C1) to (C3) is dissolved in 5 g of two different oils (H2): PrimolTM 352 and EmogreenTM L19.
  • H2 two different oils
  • the solutions thus obtained are cooled to ambient temperature and their thickening is assessed visually and/or measured at a temperature of 25° C. using a Brookfield (or BKF) viscometer of the LVT type fitted with a suitable spindle (M ) and at a speed of 6 rpm (V6).

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EP22737450.1A 2021-06-23 2022-06-22 Copolymerverdickungszusammensetzung mit mindestens einem öl und mindestens einem poly(itaconat) zur verdickung polarer oder apolarer öle Pending EP4358933A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR2106666A FR3124380A1 (fr) 2021-06-23 2021-06-23 Composition copolymérique épaississante (C) d’huiles polaires ou apolaires (H2), comprenant au moins une huile (H1) et au moins un poly(itaconate)
PCT/EP2022/067062 WO2022268906A1 (fr) 2021-06-23 2022-06-22 Composition copolymérique épaississante d'huiles polaires ou apolaires, comprenant au moins une huile et au moins un poly(itaconate)

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EP4358933A1 true EP4358933A1 (de) 2024-05-01

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EP (1) EP4358933A1 (de)
JP (1) JP2024526101A (de)
KR (1) KR20240024202A (de)
CN (1) CN117479921A (de)
FR (1) FR3124380A1 (de)
WO (1) WO2022268906A1 (de)

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US4663385A (en) * 1982-11-17 1987-05-05 Rohm And Haas Process for thickening with copolymers of alkyl poly (oxyalkylene) itaconic di-esters
FR2721607B1 (fr) 1994-06-28 1996-10-31 Seppic Sa Nouveaux dérivés d'ammoniums quaternaires, leur procédé de préparation et leur utilisation comme agents de surface.
FR2761595B1 (fr) 1997-04-04 1999-09-17 Oreal Compositions comprenant des santalines, santarubines pour la coloration artificielle de la peau et utilisations
CA2487945A1 (fr) 2002-06-11 2003-12-18 L'oreal Utilisation d'un agent mimetique de l'activite de la dopachrome tautomerase (trp-2) comme agent protecteur des melanocytes du follicule pileux et applications
FR3029525B1 (fr) * 2014-12-04 2017-01-06 Valagro Carbone Renouvelable Poitou Charentes Poly(itaconate) reticule biosource, compositions l'incluant et utilisations comme polymere super absorbant
KR102011109B1 (ko) * 2019-03-25 2019-08-16 리봄화장품 주식회사 소듐폴리이타코네이트를 함유하는 화장료 조성물 및 이의 제조방법

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WO2022268906A1 (fr) 2022-12-29

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