EP4188970A1 - Verdickungsmittel für eine hydroalkoholische zusammensetzung - Google Patents

Verdickungsmittel für eine hydroalkoholische zusammensetzung

Info

Publication number
EP4188970A1
EP4188970A1 EP21762068.1A EP21762068A EP4188970A1 EP 4188970 A1 EP4188970 A1 EP 4188970A1 EP 21762068 A EP21762068 A EP 21762068A EP 4188970 A1 EP4188970 A1 EP 4188970A1
Authority
EP
European Patent Office
Prior art keywords
weight
acid
compound
chosen
monomer
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
EP21762068.1A
Other languages
English (en)
French (fr)
Inventor
Yves Kensicher
Benoit Magny
Laurie PARRENIN
Jean Marc Suau
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.)
Coatex SAS
Original Assignee
Coatex SAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Coatex SAS filed Critical Coatex SAS
Publication of EP4188970A1 publication Critical patent/EP4188970A1/de
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
    • 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
    • C08F2/12—Polymerisation in non-solvents
    • C08F2/16—Aqueous medium
    • C08F2/22—Emulsion polymerisation
    • C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
    • C08F2/26—Emulsion polymerisation with the aid of emulsifying agents anionic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1802—C2-(meth)acrylate, e.g. ethyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D133/00—Coating compositions based on 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; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09D133/08—Homopolymers or copolymers of acrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3757—(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions
    • C11D3/3765—(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions in liquid compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
    • C11D3/3773—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines in liquid compositions
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/33—Synthetic macromolecular compounds
    • D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H17/37—Polymers of unsaturated acids or derivatives thereof, e.g. polyacrylates

Definitions

  • the invention relates to a thickening agent P for an aqueous composition, in particular for a hydro-alcoholic composition.
  • the thickening agent P is prepared in the absence of acrylamide by a polymerization reaction using N-methylol-acrylamide or one of its derivatives, an acid and an acid ester.
  • a particular condensate of (meth)acrylic acid and N-methylol-acrylamide forms part of the invention.
  • the invention also provides a hydro-alcoholic composition whose viscosity is controlled.
  • an aqueous composition When using an aqueous composition, the appearance and shape of this composition are essential properties. In particular, to facilitate its use but also to improve its effectiveness, an aqueous composition must have a controlled viscosity. In particular, a hydro-alcoholic composition must have a viscosity suitable for its use.
  • a hydro-alcoholic composition comprises a high proportion of at least one alcohol, in particular a high proportion of ethanol or isopropanol.
  • Controlling viscosity when preparing stable hydro-alcoholic compositions is generally difficult for several reasons. Indeed, the addition of alcohol in an aqueous composition tends to substantially reduce the surface tension, thus making it difficult to maintain its viscosity. Moreover, the addition of alcohol in such an aqueous composition can increase the solubility of other ingredients and thus destabilize the hydro-alcoholic composition.
  • aqueous compositions in particular hydroalcoholic compositions
  • the thickening agents of aqueous compositions are not always sufficiently effective in the face of the various problems encountered.
  • Document WO 2006016035 discloses hydro-alcoholic compositions comprising a thickening hydrophobic compound.
  • JP 2019003926 discloses thickening compounds for electrode preparation suspension.
  • JP S4828555 discloses unsaturated compounds.
  • GB 1356030 discloses binder compounds for coating paper.
  • Document DE 2531235 discloses thickening compounds for paint or for printing paste.
  • a thickening agent for aqueous composition in particular for hydro-alcoholic composition
  • having such an agent in the form of an aqueous dispersion or else in solid form and easily incorporated into such a composition is particularly advantageous.
  • Using a thickening agent in powder form can in particular avoid the use of an organic solvent other than an alcohol. Avoiding any organic solvent other than an alcohol in an aqueous composition, in particular in a hydro-alcoholic composition, then makes it possible to limit or eliminate the problems associated with these solvents, in particular the problems associated with their handling or even the problems regulatory or health related to their presence.
  • the preparation of a hydro-alcoholic composition can also cause problems.
  • the complete and homogeneous incorporation of the different ingredients is essential.
  • Stability, in particular the maintenance of viscosity, is also an important property of thickened aqueous compositions, in particular for thickened aqueous-alcoholic compositions.
  • the invention makes it possible to provide a solution to all or part of the problems of thickening agents for aqueous compositions, in particular thickeners for hydro-alcoholic compositions, of the state of the art.
  • the invention provides a thickening agent P prepared, in the absence of acrylamide, by at least one polymerization reaction: at. from more than 30% by weight to 69.75% by weight of at least one anionic monomer (a) chosen from acrylic acid, a salt of acrylic acid, methacrylic acid, a salt of methacrylic acid and their combinations; b. from 29.75% by weight to less than 65% by weight of at least one nonionic monomer (b) chosen from C 1 -C 8 esters of an acid chosen from acrylic acid, methacrylic acid and combinations thereof; vs. from 0.5 to 5% by weight of at least one compound (c) of formula I: in which :
  • R 1 independently represents H or CH3,
  • R 2 and R 3 identical or different, independently represent H, CH3 or CH2CH3, relative to the total quantity by weight of monomers (a), (b) and (c).
  • compound (b) is chosen from methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, ethylhexyl acrylate, methyl methacrylate, ethyl methacrylate, propyl methacrylate , butyl methacrylate, ethylhexyl methacrylate, vinyl acetate and combinations thereof. More preferably according to the invention, compound (b) is chosen from ethyl acrylate, butyl acrylate, methyl methacrylate and combinations thereof.
  • compound (c) is a compound of formula I in which R 2 and R 3 represent H. More preferably according to the invention, compound (c) is chosen from N-methylol -acrylamide, N-methylol-methacrylamide, more preferably N-methylol-acrylamide.
  • the agent P is totally or partially neutralized, preferably by means of at least one compound chosen from NaOH, KOH, ammonium derivatives, ammonia, amino bases, for example triethanolamine or 2-amino -2-methyl-propanol (AMP) and combinations thereof. More preferably, the agent P is neutralized by means of at least one compound chosen from amino bases, for example triethanolamine or 2-amino-2-methyl-propanol (AMP).
  • the agent P can also be totally or partially coacervated.
  • the agent P is totally or partially coacervated by reducing the pH, for example by reducing the pH to a value below 6.5, in particular by means of an acid compound, in particular by means of at least one organic or mineral acid compound, in particular an acid compound chosen from phosphoric acid, citric acid, glucono-lactone, lactic acid, salicylic acid, glycolic acid, ascorbic acid, glutamic acid, hydrochloric acid, acetic acid, D-gluconic acid, sulphonic acid , methane sulfonic acid, benzimidazole sulfonic acid, tartaric acid, 4-aminobenzoic acid, benzoic acid, sorbic acid, phenylbenzimidazole sulfonic acid, benzylidene camphor sulfonic acid, terephthalylidene dicamphor sulfonic acid, kojic acid, hyaluronic acid.
  • an acid compound in particular by means of at least one organic or
  • the agent P is totally or partially coacervated by increasing the ionic strength, for example by adding at least one ionized compound or at least one salt, in particular NaCl, KCl, MgClb, CaCb, MgSCU , CaSCU, or by adding phenylbenzimidazole sulphonic acid (PBSA) or sodium salt of pyroglutamic acid (NaPCA) or else by adding at least one ionized organic sunscreen.
  • PBSA phenylbenzimidazole sulphonic acid
  • NaPCA sodium salt of pyroglutamic acid
  • the polymerization reaction implements:
  • Agent P according to the invention is prepared from the essential compounds (a), (b) and (c) in the absence of acrylamide.
  • Compounds (a), (b) and (c) can be implemented alone or combined with one or more other compounds or monomers.
  • the invention provides an agent Pa according to the invention which is prepared from only compounds (a), (b) and (c).
  • the agent P according to the invention is prepared from a polymerization reaction which also uses at least one particular additional compound.
  • a particular additional compound is a non-ionic monomer (d) chosen from the Ci-Cs esters of an acid chosen from itaconic acid and acid maleic acid, preferably a monomer (d) chosen from methyl itaconate, ethyl itaconate, propyl itaconate, butyl itaconate, methyl maleate, ethyl maleate, propyl maleate, butyl maleate and combinations thereof.
  • the monomer (d) can be implemented in an amount ranging from 5 to 30% by weight of the amount of non-ionic monomer (b) implemented.
  • another particular additional compound is a compound (e) of formula II: in which :
  • T 1 and T 2 identical or different, independently represent H or CH3,
  • Q 1 and Q 2 identical or different, independently represent H, CH3 or CH2CH3.
  • compound (e) is prepared by a prior reaction or by an in situ reaction between at least one compound (a) and at least one compound (c) of formula (I) defined according to invention.
  • the polymerization reaction can implement less than 8% by weight, preferably from 0.2 to 8% by weight, in particular from 0.5 to 5% by weight, of monomer (e) with respect to to the total amount by weight of monomers.
  • another particular additional compound is a compound (f) chosen from 2-acrylamido-2-methylpropane sulphonic acid, ethoxymethacrylate sulphonic acid, sodium methallyl sulphonate, styrene sulphonate phosphated hydroxyethyl-acrylate, hydroxypropyl- phosphate acrylate, phosphate hydroxyethylhexyl acrylate, phosphate hydroxyethyl methacrylate, phosphate hydroxypropyl methacrylate, phosphate hydroxyethylhexyl methacrylate, their salts and their combinations.
  • 2-Acrylamido-2-methylpropane sulfonic acid is the preferred compound (f).
  • the polymerization reaction can implement less than 20% by weight, preferably from 0.2 to 20% by weight, in particular from 0.5 to 10% by weight, of monomer (f) with respect to to the total amount by weight of monomers.
  • another particular additional compound is a compound (g) chosen from hydroxyethyl-acrylate, hydroxypropyl-acrylate, hydroxyethylhexyl-acrylate, hydroxyethyl-methacrylate, hydroxypropyl-methacrylate, hydroxyethylhexyl-methacrylate.
  • the polymerization reaction can implement less than 20% by weight, preferably from 0.2 to 20% by weight, in particular from 0.5 to 10% by weight, of monomer (g) relative to the total amount by weight of monomers.
  • another particular additional compound is a crosslinking monomer
  • the polymerization reaction can implement less than 5% by weight, preferably from 0.01 to 4% by weight, in particular from 0.02 to 4% by weight or from 0.02 to 2% by weight, in particular from 0.02 to 1% by weight, of monomer (h) relative to the total quantity by weight of monomers.
  • another particular additional compound is an associative monomer
  • n identical or different, independently represent 0 or an integer or decimal number less than 150, m or n is different from 0,
  • - OE independently represents a CH2CH2O group
  • - OP independently represents a group chosen from CH(CH3)CH2O and CH 2 CH(CH 3 )O,
  • G 1 represents a group comprising at least one polymerizable olefinic unsaturation, preferably an acrylate group or a methacrylate group and
  • - G 2 represents a Cô-C40-alkyl group, linear or branched, a phenyl group, a polyphenyl group, preferably a Cio-Cso-alkyl group, linear or branched, more preferably a Ci2-C22-alkyl group, linear or branched, or a group comprising 2 to 5 phenyls or a tristyrylphenyl group or a pentastyrylcumylphenyl group.
  • the polymerization reaction can implement less than 20% by weight, preferably from 0.05 to 20% by weight, in particular from 0.1 to 10% by weight, of monomer (i) relative to the total amount by weight of monomers.
  • the invention provides a Pb agent prepared from compounds (a), (b) and (c) and at least one compound (f), preferably 2-acrylamido-2-methylpropane acid sulfonic.
  • the invention provides an agent Pc prepared from compounds (a), (b) and (c) and from at least one compound (i).
  • the invention provides a Pd agent prepared from compounds (a), (b) and (c), at least one compound (f), preferably 2-acrylamido-2-methylpropane acid sulfonic, and at least one compound (i). Also advantageously, the invention provides an agent Pe prepared from compounds (a), (b) and (c) and from at least one compound (h). Also advantageously, the invention provides a Pf agent prepared from compounds (a), (b) and (c) and at least one compound (e).
  • the agent P according to the invention has a glass transition temperature greater than -10°C or greater than 0°C.
  • the glass transition temperature of agent P is greater than 15°C or greater than 25°C.
  • the agent P according to the invention is in solid form, more preferably in powder form.
  • agent P may comprise the implementation of a compound (e) of formula II.
  • the invention also provides a compound (e) of formula II: in which :
  • T 1 and T 2 identical or different, independently represent H or CH3,
  • Q 1 and Q 2 identical or different, independently represent H, CH3 or CH2CH3.
  • the compound (e) according to the invention is a compound of formula II in which Q 1 and Q 2 represent H.
  • the particularly preferred compound (e) according to the invention is chosen from:
  • Compound (e3) is more particularly preferred according to the invention.
  • Compound (e) according to the invention can be prepared by a condensation reaction of at least one compound (a) according to the invention with at least one compound (c) according to the invention.
  • the invention also provides a method for preparing a copolymer, in particular a copolymer of the (H)ASE type [(Hydrophobized) Alkali-Swellable Emulsion or alkali-swellable polymeric emulsion which can be treated hydrophobically], by reaction polymerization of a compound (e) according to the invention with at least one polymerizable compound, in particular with at least one polymerizable compound chosen from a compound (a) according to the invention, a compound (b) according to the invention and their combinations.
  • This polymerization reaction can also implement at least one other additional compound chosen from a compound (c) according to the invention, a compound (d) according to the invention, a compound (f) according to the invention, a compound ( g) according to the invention, a compound (h) according to the invention, a compound (i) according to the invention and their combinations.
  • Agent P according to the invention is a particularly effective thickening agent, in particular for controlling the viscosity of an aqueous composition.
  • the invention provides a method for controlling the viscosity of an aqueous composition comprising the addition to an aqueous composition of at least one agent P according to the invention.
  • the thickened aqueous composition obtained also forms part of the invention.
  • the invention therefore also provides an aqueous composition C comprising water and at least one agent P according to the invention.
  • the composition C according to the invention is chosen from a detergent composition, a sanitary composition, a disinfectant composition, a cosmetic composition, a coating composition, a paper coating slip, a printing composition textile, a textile coating composition.
  • the preferred sanitary or disinfectant compositions according to the invention are chosen from an antibacterial composition, a bactericidal composition, a biocidal composition, a bacteriostatic composition, an antiviral composition.
  • composition C also comprises at least one additive chosen from an alcohol, an oxidizing compound, an emollient compound, a surfactant compound and combinations thereof. More preferably according to the invention, composition C also comprises at least one alcohol and optionally at least one additive chosen from an oxidizing compound, an emollient compound, a surfactant compound and combinations thereof.
  • the alcohol used is chosen from ethanol, n-propanol, isopropanol and their combinations.
  • composition C according to the invention comprises:
  • the agent P according to the invention makes it possible to effectively control the viscosity of an aqueous composition.
  • the invention provides a composition C according to the invention which has a Brookfield viscosity measured at 25° C. and at 6 rpm of between 800 and 20,000 mPa.s, preferably between 1,000 and 15,000 mPa.s or between 5,000 to 15,000 mPa.s.
  • composition according to the invention is in the form of a gel or in the form of a mousse.
  • composition C according to the invention can be used in different media, in particular in an acidic medium or in a basic medium.
  • composition C according to the invention has a pH greater than 6 or greater than 6.5.
  • composition C according to the invention has a pH of less than 13, preferably less than 12, more preferably less than 11. More preferably, composition C according to the invention has a pH ranging from 6 to 13 or from 6 to 12 or from 6 to 11, also more preferably ranging from 6.5 to 13 or from 6.5 to 12 or from 6.5 to 11.
  • the invention also provides a method for preparing a hydroalcoholic solution comprising mixing in water at least one agent P according to the invention and at least one alcohol and optionally at least one additive chosen from a oxidant compound, emollient compound, surfactant compound and combinations thereof.
  • the reagents used are acrylic acid (AA), methacrylic acid (AMA), ethyl acrylate (AE), butyl acrylate (ABu), N-methylol- acrylamide (NMA), 2-acrylamido-2-methylpropane sulfonic acid (AMPS as the sodium salt in 50% aqueous solution).
  • Example 1 preparation and characterization of agents P according to the invention
  • the contents of the reactor are heated to a temperature of 86°C ⁇ 2°C.
  • the reagents of the 2 beakers are introduced into the polymerization reactor at a temperature of 86°C ⁇ 2°C.
  • a copolymer (PI) with 30.5% by weight of dry extract is obtained, the composition of which is detailed in Table 1.
  • the contents of the reactor are heated to a temperature of 86°C ⁇ 2°C.
  • the reagents of the 2 beakers are introduced into the polymerization reactor at a temperature of 86°C ⁇ 2°C.
  • a copolymer (P2) with 30.5% by weight of dry extract is obtained, the composition of which is detailed in Table 1.
  • the contents of the reactor are heated to a temperature of 86°C ⁇ 2°C.
  • the reagents of the 2 beakers are introduced into the polymerization reactor at a temperature of 86°C ⁇ 2°C.
  • a copolymer (P3) with 30.2% by weight of dry extract is obtained, the composition of which is detailed in Table 1.
  • an initial charge is introduced consisting of 450 g of deionized water, 2.97 g of sodium dodecyl sulphate.
  • a first glass beaker and according to the proportions presented in Table 1, 126.77 g of monomer (a) 158.25 g of monomer (b), 4.46 g of monomer (c) of formula I in in which R 1 , R 2 and R 3 represent H, 7.90 g of monomer (i) compound of formula III in which G 1 represents a methacrylate group, G 2 represents a linear C22-alkyl group, m represents 25 and n represents 0 (C22-OE25 methacrylate), 1.76 g sodium dodecyl sulfate and 130 g deionized water.
  • the contents of the reactor are heated to a temperature of 86°C ⁇ 2°C.
  • the reagents of the 2 beakers are introduced into the polymerization reactor at a temperature of 86°C ⁇ 2°C.
  • a copolymer (P4) with 30.4% by weight of dry extract is obtained, the composition of which is detailed in Table 1.
  • the contents of the reactor are heated to a temperature of 86°C ⁇ 2°C.
  • the reagents of the 2 beakers are introduced into the polymerization reactor at a temperature of 86°C ⁇ 2°C.
  • a copolymer (P5) with 30.7% by weight of dry extract is obtained, the composition of which is detailed in Table 1.
  • the contents of the reactor are heated to a temperature of 76°C ⁇ 2°C.
  • the reagents of the 4 containers are introduced into the polymerization reactor at a temperature of 86°C ⁇ 2°C.
  • a copolymer (P6) with 30.2% by weight of dry extract is obtained, the composition of which is detailed in Table 1.
  • the contents of the reactor are heated to a temperature of 86°C ⁇ 2°C.
  • the reagents of the 2 beakers are introduced into the polymerization reactor at a temperature of 86°C ⁇ 2°C.
  • a copolymer (P7) with 31.3% by weight of dry extract is obtained, the composition of which is detailed in Table 1.
  • Example 2 preparation and characterization of comparative copolymers
  • the synthesis process is analogous to the process for preparing the agent PL In a first glass beaker and according to the proportions presented in Table 2, 112.98 g of monomer (a), 159.13 g of monomer ( b), 0.695 g of monomer (h) diallyl phthalate, 1.92 g of sodium dodecyl sulfate and 140 g of deionized water.
  • the contents of the reactor are heated to a temperature of 86°C ⁇ 2°C.
  • the reagents of the 2 beakers are introduced into the polymerization reactor at a temperature of 86°C ⁇ 2°C.
  • PCI copolymer
  • Table 2 A copolymer (PCI) with 30.1% by weight of dry extract is obtained, the composition of which is detailed in Table 2.
  • the synthetic process is analogous to the process for preparing agent P2.
  • a first glass beaker and according to the proportions presented in Table 2, 123.65 g of monomer (a), 165.30 g of monomer (b), 11.50 g of monomer (i) compound of formula III in which G 1 represents a methacrylate group, G 2 represents a linear C22-alkyl group, m represents 25 and n represents 0 (C22-OE25 methacrylate), 1.92 g of sodium dodecyl sulfate and 140 g of deionized water .
  • the contents of the reactor are heated to a temperature of 86°C ⁇ 2°C.
  • the reagents of the 2 beakers are introduced into the polymerization reactor at a temperature of 86°C ⁇ 2°C.
  • a copolymer (PC2) with 30.0% by weight of dry extract is obtained, the composition of which is detailed in Table 2.
  • Example 3 preparation and characterization of hydro-alcoholic compositions according to the invention and of comparative hydro-alcoholic compositions
  • hydro-alcoholic compositions C1 to C5 and CCI and CC2 are prepared using the ingredients mixed in water according to the amounts presented in Table 3.
  • phase A In a 250 mL beaker fitted with a stirrer with a 40 mm diameter Rayneri-type blade, the ingredients of phase A are added until a homogeneous mixture is obtained. While stirring, the thickening agent or copolymer of phase B is added, then the neutralizing agent of phase C. The stirring speed is increased when the viscosity increases, avoiding the incorporation of air. After all the neutralizing agent has been added, agitation is maintained for 10 minutes.
  • the agent P according to the invention makes it possible to prepare hydro-alcoholic compositions having a high viscosity which is essential for the use of these compositions. This viscosity control is obtained with an agent P which is prepared in the absence of acrylamide.
  • the comparative copolymers do not make it possible to achieve an acceptable viscosity for the hydro-alcoholic compositions.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Cosmetics (AREA)
EP21762068.1A 2020-08-03 2021-07-29 Verdickungsmittel für eine hydroalkoholische zusammensetzung Pending EP4188970A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR2008245A FR3113057B1 (fr) 2020-08-03 2020-08-03 Agent épaississant pour composition hydro-alcoolique
PCT/FR2021/000087 WO2022029372A1 (fr) 2020-08-03 2021-07-29 Agent epaississant pour composition hydro-alcoolique

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EP4188970A1 true EP4188970A1 (de) 2023-06-07

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US (1) US20230287162A1 (de)
EP (1) EP4188970A1 (de)
CN (1) CN116096342A (de)
FR (1) FR3113057B1 (de)
WO (1) WO2022029372A1 (de)

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4828555B1 (de) 1969-07-14 1973-09-03
FR2087531A5 (de) * 1970-05-22 1971-12-31 Ugine Kuhlmann
JPS512114B2 (de) * 1971-08-18 1976-01-23
DE2531235A1 (de) * 1975-07-12 1977-02-03 Basf Ag Verdickungsmittel fuer polymerisatdispersionen
FR2872815B1 (fr) * 2004-07-08 2008-06-27 Coatex Soc Par Actions Simplif Utilisation de copolymeres acryliques hydrosolubles dans des formations aqueuses eventuellement pigmentees et formulations obtenues
FR2879607B1 (fr) * 2004-12-16 2007-03-30 Seppic Sa Nouveaux latex inverse concentre, procede pour sa preparation, et utilisation dans l'industrie
BR112014017892B1 (pt) * 2012-01-31 2019-05-07 Unilever N.V. Composição para o tratamento do cabelo
FR2987839B1 (fr) * 2012-03-08 2014-05-09 Soc Dexploitation De Produits Pour Les Industries Chimiques Seppic Nouveau polymere d'acrylate de silicone et d'acide acrylique epaississant et reduisant le caractere collant des formules cosmetiques a base de glycerine
JP2019003926A (ja) * 2017-06-09 2019-01-10 松本油脂製薬株式会社 蓄電デバイススラリー及びその利用

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WO2022029372A1 (fr) 2022-02-10
FR3113057B1 (fr) 2023-09-29
CN116096342A (zh) 2023-05-09
FR3113057A1 (fr) 2022-02-04
US20230287162A1 (en) 2023-09-14

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