EP1989257A1 - Utilisation de polymeres ou copolymeres particuliers en tant qu'agent tensio-actif pour la stabilisation de latex - Google Patents

Utilisation de polymeres ou copolymeres particuliers en tant qu'agent tensio-actif pour la stabilisation de latex

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Publication number
EP1989257A1
EP1989257A1 EP07726611A EP07726611A EP1989257A1 EP 1989257 A1 EP1989257 A1 EP 1989257A1 EP 07726611 A EP07726611 A EP 07726611A EP 07726611 A EP07726611 A EP 07726611A EP 1989257 A1 EP1989257 A1 EP 1989257A1
Authority
EP
European Patent Office
Prior art keywords
group
representing
monomers
chosen
heteroatoms
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.)
Withdrawn
Application number
EP07726611A
Other languages
German (de)
English (en)
French (fr)
Inventor
Jean-Luc Couturier
Manuel Hidalgo
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.)
Arkema France SA
Original Assignee
Arkema France SA
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 Arkema France SA filed Critical Arkema France SA
Publication of EP1989257A1 publication Critical patent/EP1989257A1/fr
Withdrawn legal-status Critical Current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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
    • 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
    • C08F2/30—Emulsion polymerisation with the aid of emulsifying agents non-ionic
    • 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
    • C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
    • 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
    • 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
    • C08F4/00—Polymerisation catalysts
    • 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
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/08—Homopolymers or copolymers of acrylic acid esters
    • 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
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/47—Levelling agents

Definitions

  • the present invention relates to the use of particular polymers or copolymers as surfactants for the stabilization of latices, in particular acrylic latices.
  • the general field of the invention is that of latex.
  • the latices are in the form of a composition comprising, in suspension, microscopic particles of polymer chains in a continuous liquid medium, most often aqueous, which can serve as a base, among other applications, for glues, paints, binders for textiles, inks (especially acrylic latexes).
  • the invention relates to a composition comprising at least one latex and at least one surfactant obtainable by a process for the polymerization of one or more monomers, said method comprising a contacting step, for example, in a medium comprising water, said monomer or monomers with at least one initiator corresponding to the following formula (I):
  • R 1 represents a hydrogen atom, a linear or branched alkyl group comprising from 1 to 8 carbon atoms, a phenyl group, a metal chosen from alkali metals, alkaline earth metals and transition metals, in particular, an alkali metal (Na, Li, K) or H 4 N + , Bu 4 N + , Bu 3 HN + , Bu representing an n-butyl group;
  • - R 2 and R 3 identical or different, represent a linear or branched alkyl group comprising from 1 to 3 carbon atoms;
  • R 5 represents a hydrogen atom or a group - OCORs, R-8 representing a linear or branched alkyl group comprising from 1 to 20 carbon atoms;
  • Re and R.7 represent, independently, a linear or branched alkyl group having from 1 to 3 carbon atoms;
  • R 4 represents:
  • heterocyclic group comprising one or more heteroatoms chosen from O, N and / or S, said heterocyclic group optionally carrying an acid group comprising at least one heteroatom chosen from S and P or carrying at least one hydrocarbon group comprising optionally one or more heteroatoms (for example N, S and / or O), said hydrocarbon group carrying at least one acid group as defined above, said heterocyclic group may exist in the form of a salt; or
  • a -CO-NR-Y or -CO-OY group with Y representing a hydrocarbon group optionally comprising one or more heteroatoms (for example, N, S and / or O) bearing at least one acid group comprising a heteroatom selected from S and P or a hydrocarbon group optionally comprising one or more heteroatoms (eg, N, S and / or O) containing at least one heterocyclic group comprising one or more heteroatoms selected from N, O and S, said -CO-NR-Y or -CO-OY group may optionally exist in the form of a salt and R representing a hydrogen atom or an alkyl group, preferably comprising from 1 to 24 carbon atoms.
  • R 4 may be an aryl group comprising, for example from 5 to 20 carbon atoms (for example, a phenyl group), said aryl group being carrier (that is to say substituted) of at least one acid group comprising at least one heteroatom selected from S and P, said acid group may exist in the form of a salt.
  • an acid group comprising at least one heteroatom selected from S and P there may be mentioned a sulphonic, phosphonic, phosphoric or phosphinic group and the salts thereof.
  • R 4 may be a heterocyclic group comprising one or more heteroatoms chosen from O, N and / or S, such as a pyrrole, pyridine, indole, thiophene, furan or pyrimidine group, optionally carrying at least an acid group comprising at least one heteroatom selected from S and P as defined above or said heterocyclic group carrying a hydrocarbon group, such as an alkyl group having 1 to 24 carbon atoms, optionally comprising one or more heteroatoms, which hydrocarbon group is substituted one or more times with an acid group as defined above (i.e. an acid group comprising at least one a heteroatom selected from S and P).
  • a heterocyclic group comprising one or more heteroatoms chosen from O, N and / or S, such as a pyrrole, pyridine, indole, thiophene, furan or pyrimidine group, optionally carrying at least an acid group comprising at least one heteroatom selected from S and P as defined above or said heterocyclic
  • R 4 may represent a group -CO-NR-Y or -CO-OY, with Y representing a hydrocarbon-based group, such as an alkyl group possibly comprising from 1 to 24 carbon atoms, optionally comprising one or several heteroatoms, and substituted by at least one acid group comprising at least one heteroatom selected from S and P, such as a sulfonic, phosphonic, phosphoric or phosphinic group.
  • Y may also be a hydrocarbon group, such as an alkyl group comprising from 1 to 24 carbon atoms.
  • the group Y can not be an unsubstituted alkyl group, since it is necessarily substituted by an acid group or a heterocyclic group as defined above.
  • R 4 is an aryl group carrying at least one acid group comprising at least one chosen heteroatom. from S and P, said acid group may exist as a salt.
  • R 4 may advantageously be a phenylene group bearing a group -SO 3 R 9 , R 8 representing a hydrogen atom, a metal chosen from alkali metals, alkaline earth metals, transition metals, in particular in particular, an alkali metal (Na, Li, K), or also H 4 N + , Bu 4 N + , Bu 3 HN + , Bu representing an n-butyl group.
  • a particular initiator according to the invention corresponds to the following formula (II):
  • the initiators described above can be obtained by radical addition of the 1,2-type of an olefin to a starting alkoxyamine, according to the following reaction scheme: a) cleavage of the starting alkoxyamine in free radicals:
  • the process is advantageously carried out in a medium comprising, in particular, water.
  • This medium may be an aqueous or predominantly aqueous solution or a dispersed phase medium aqueous / organic phase (dispersion, emulsion, mini-emulsion, microemulsion, suspension, micellar, reverse suspension, inverse emulsion, inverse microemulsion).
  • the surfactants present in the compositions of the invention are very advantageously in the form of an amphiphilic copolymer, namely a copolymer having both hydrophilic and hydrophobic parts, the hydrophilic parts resulting from the polymerization of a or more hydrophilic monomers, and the hydrophobic portions resulting from the polymerization of one or more hydrophobic monomers.
  • hydrophilic monomers will, in particular, be monomers whose patterns after polymerization will be different from the -CH2-CHR4- unit present in the polymerization initiator as defined above.
  • hydrophilic monomer or monomers may be chosen from:
  • water-soluble derivatives of styrene such as sodium styrene sulphonate
  • water-soluble acrylic monomers such as acrylic acid and its salts, methyl acrylate, 2-hydroxyethyl acrylate, 2-methoxyethyl acrylate, methoxypolyethylene glycol acrylates, ethoxypolyethylene glycol acrylates, acrylates of methoxy-polyethylene glycol-polypropylene glycol and mixtures thereof, 2- (dimethylamino) ethyl acrylate (ADAME), chloride or sulfate of (acryloyloxy) ethyl] trimethylammonium, chloride or
  • -Itaconic acid maleic acid and its salts, maleic anhydride, alkyl or alkoxy maleates or hemimaleates or aryloxypolyalkyleneglycol, vinylpyridine, vinylpyrrolidinone; and
  • Water-soluble monomers of particular interest in the context of this invention are:
  • amine salt (meth) acrylates such as [2- (methacryloyloxy) ethyl] trimethylammonium chloride or sulfate, [2- (methacryloyloxy) ethyl] dimethylbenzylammonium chloride or sulfate;
  • hydroxyalkyl (meth) acrylates such as 2-hydroxyethyl methacrylate
  • - (meth) acrylates of polyethylene glycol, of alkoxy- or aryloxy ⁇ polyalkylene glycol such as (meth) acrylates, methoxypolyethylene glycol (meth) acrylates, ethoxypolyethylene; and - mixtures thereof.
  • the hydrophobic monomer or monomers may be chosen from:
  • vinylaromatic monomers such as styrene, ⁇ -methylstyrene; diene monomers, such as butadiene, isoprene;
  • hydrophobic acrylate monomers such as ethyl acrylate, n-butyl acrylate, ethylhexyl acrylate, phenyl acrylate, methoxypolypropylene glycol acrylates, fluorinated acrylates or silyl acrylates; methacrylate monomers, such as methyl methacrylate, lauryl, cyclohexyl, allyl, phenyl, methoxypolypropylene glycol methacrylates, 2- (tert-butylamino) ethyl methacrylate (MATBAE), fluorinated methacrylates, such as 2,2,2-trifluoroethyl methacrylate, silylated methacrylates such as 3-methacryloylpropyltrimethylsilane; Acrylonitrile; and mixtures thereof.
  • methacrylate monomers such as methyl methacrylate, lauryl, cyclohexyl, allyl,
  • a surfactant according to the invention is for example a copolymer comprising hydrophilic units derived from the polymerization of methacrylic acid and hydrophobic units derived from the polymerization of methyl methacrylate.
  • the initiator (s) of formula (I) may be present in a content ranging from 0.005% to 40% by weight relative to the total weight of the monomer (s) used and, preferably, at a content ranging from 0.01% at 10%.
  • the monomer (s) and / or the alkoxyamine type initiator may optionally be introduced continuously into the polymerization medium.
  • the contacting step can be carried out, in addition to the initiator of formula (I), in the presence of an initiator chosen from hydroperoxides and dialkyl peroxides. , diacyl peroxides, peroxyesters, peroxydicarbonates, peroxyacetals or azo compounds.
  • an initiator chosen from hydroperoxides and dialkyl peroxides. , diacyl peroxides, peroxyesters, peroxydicarbonates, peroxyacetals or azo compounds.
  • hydroperoxides that may be mentioned include tert-butyl hydroperoxide, Tert-amyl hydroperoxide, cumyl hydroxide, 2,5-dimethyl-2,5-di (hydroperoxy) hexane, diisopropylbenzene monohydroperoxide and paramenthane hydroperoxide.
  • dialkyl peroxides examples include 2,5-dimethyl-2,5-di (tert-butylperoxy) hexyne- (3), di-tert-butyl peroxide, di-tert-butyl peroxide and di-tert-butyl peroxide.
  • diacyl peroxide there may be mentioned benzoyl peroxide, lauroyl peroxide, decanoyl peroxide, 3,5,5-trimethylhexanoyl peroxide, acetyl peroxide and cyclohexylsulphonyl peroxide.
  • peroxyesters there may be mentioned tert-butyl peroxybenzoate, tert-butyl peroxyacetate, tert-butyl peroxy-3,5,5-trimethylhexanoate and peroxy-3,5,5-trimethylhexanoate.
  • peroxydicarbonates there may be mentioned di (2-ethylhexyl) peroxydicarbonate, dicyclohexyl peroxydicarbonate, di (n-propyl) peroxydicarbonate, di (4-tert-butylcyclohexyl) peroxydicarbonate.
  • peroxyacetals By way of examples of peroxyacetals, mention may be made of 1,1-di (tert-butylperoxy) cyclohexane, 1,1-di (tert-butylperoxy) 3, 3, 5-trimethylcyclohexane and 3,3-di ( tert-butylperoxy) ethyl butyrate, ethyl 3,3-di (tert-amylperoxy) butyrate, 4,4-di (tert-butylperoxy) n-butyl valerate, 2,2-di (tert butylperoxy) butane, 1,1-di (tert-amylperoxy) cyclohexane, 2,2-bis [4,4-di (tert-butylperoxy) cyclohexyl] propane.
  • the contacting step may also be carried out in the presence of inorganic oxidants such as sodium persulfates, potassium or ammonium, hydrogen peroxide, perchlorates, percarbonates, ferric salts. These oxidants may be used alone or in combination with inorganic or organic reducers such as sodium or potassium bisulfite and metabisulfite, vitamin C, sodium or potassium hypophosphites. These organic or inorganic reducers can also be used alone, that is to say, in the absence of inorganic oxidants.
  • the process of the invention may comprise a step of in situ preparation of the initiator of formula (I), preferably before the contacting step. From a structural point of view, the surfactants, in addition to the repeating units resulting from the polymerization of the monomers, have at least one reactive end having the following formula:
  • the polymers or copolymers will in particular have a unit of formula -CH 2 -CHR 4 - derived from the alkoxyamine present at the end of chains, the other units resulting from the polymerization of the monomers, which units will be different from said unit -CH 2 -CHR 4 -.
  • This polymer or copolymer having such a reactive end can be made to undergo a chemical transformation of this end by reaction thereof with appropriate reagents.
  • the latices present in the compositions of the invention may be latexes obtained by emulsion polymerization, in particular alkalinity-swelling emulsion type latices, better known as ASE latex (corresponding to the English terminology “Alkali Swellable Emulsions"). ").
  • ASE latex alkalinity-swelling emulsion type latices
  • the latex obtained by emulsion polymerization in aqueous medium of methacrylic acid, methyl methacrylate, diallyl phthalate obtained by emulsion polymerization in aqueous medium of methacrylic acid, methyl methacrylate, diallyl phthalate.
  • These latices have the particularity of having thickening properties.
  • compositions may be prepared by mixing the surfactant copolymer with the precursor monomers of the latex, followed by a step of polymerizing said monomers.
  • the surfactant can be prepared in situ prior to the addition of the monomers, as well as the initiator necessary for the synthesis of the surfactant.
  • compositions according to the invention can be used in all fields using latex, namely the field of painting, textiles, cosmetics, paper, floor coverings, construction, decoration.
  • compositions of the invention can be used as dispersants in cosmetic compositions, paint compositions, ink compositions.
  • the invention relates, according to a second object to use, as a surfactant for the stabilization of a latex, a polymer or copolymer obtainable by a polymerization process of one or more monomers, comprising a step of contacting, in a medium comprising water, the or said monomers with at least one initiator corresponding to the following formula (I):
  • R 1 represents a hydrogen atom, a linear or branched alkyl group comprising from 1 to 8 carbon atoms, a phenyl group, a metal chosen from alkali metals, alkaline earth metals, transition, in particular an alkali metal (Na, Li, K), or H 4 N +, Bu 4 N +, Bu3HN +, Bu represents a n-butyl group;
  • R 2 and R 3 identical or different, represent a linear or branched alkyl group comprising from 1 to 3 carbon atoms;
  • R 5 represents a hydrogen atom or a group
  • R-8 representing a linear or branched alkyl group comprising from 1 to 20 carbon atoms
  • R 6 and R 7 independently represent a linear or branched alkyl group having 1 to 3 carbon atoms
  • R 4 represents: an aryl group carrying at least one acid group comprising at least one heteroatom selected from S and P, said acid group possibly existing in the form of a salt; or
  • heterocyclic group comprising one or more heteroatoms chosen from O, N and / or
  • said heterocyclic group optionally carrying at least one acid group comprising at least one heteroatom selected from S and P or bearing a hydrocarbon group optionally comprising one or more heteroatoms (for example N, S and / or O), said hydrocarbon group carrying at least one acid group as defined above, said heterocyclic group being able to exist in the form of a salt; or
  • a -CO-NR-Y or -CO-OY group with Y representing a hydrocarbon group optionally comprising one or more heteroatoms (for example, N, S and / or O) bearing at least one acidic group comprising a heteroatom chosen from S and P or representing a hydrocarbon group optionally comprising one or more heteroatoms (for example, N, S and / or O) containing at least one heterocyclic group comprising one or more heteroatoms chosen from N, O and S, said group - CO-NR-Y or -CO-OY which may optionally exist in the form of a salt and R representing a hydrogen atom or an alkyl group, preferably comprising from 1 to 24 carbon atoms.
  • the polymers or copolymers that can be used in this sense are the same as those described above for the compositions of the invention.
  • the product obtained is analyzed by 1 H, 13 C and 31 P NMR, by negative electrospray mass spectrometry and by Karl Fischer analysis. It contains 84% by weight of initiator of formula (II) in the form of 2 diastereoisomers in proportions of 59/41 and 16% of water.
  • the characteristics of the initiator obtained are as follows:
  • EXAMPLE 2 The following example relates to the preparation of a surfactant based on methacrylic acid and methyl methacrylate.
  • the solution 2 is added in its entirety in the reactor and the stirring speed is set at 344 revolutions per minute. Then mix 1 is added in the reactor using a dosing pump for a period of 20 minutes. The reactor is then maintained at a temperature of at least 50 ° C. for a duration of at least 4 hours. At the end of this maintenance temperature, the medium is cooled and the contents of the reactor is discharged into a suitable container.
  • the product thus obtained has a milky and slightly foaming appearance with a particle size of 169 nm measured by quasi-elastic light scattering with a Malvern LoC apparatus.
  • the following example illustrates the synthesis of a latex of the ASE type stabilized with a surfactant polymer.
  • a heat transfer fluid is introduced 303 g of the product prepared according to Example 2 consisting of a dilute aqueous dispersion of a polymeric surfactant according to the invention.
  • the stirring is started at a moderate speed, the system is heated to reach 72 ° C. in the reactor and degassed by bubbling nitrogen into the liquid for at least 15 minutes.
  • the following containers are prepared in the appropriate containers:
  • the reactor is brought to 78 ° C. and solution 2 is added in its entirety while the stirring speed is set at 344 revolutions per minute. Seven minutes after the introduction of the solution 2), the mixing of the mixture 1 to the reactor is initiated using a metering pump, so as to complete the addition of this mixture in the reactor in 2.5 hours during which the temperature is maintained at at least 78 ° C. After the addition, the medium is maintained at at least 78 ° C. for at least another 3 hours. The reactor is then cooled and its contents poured into a suitable container.
  • the product obtained is a stable latex of the ASE type with a dry extract of 27.6% measured by gravimetry and a particle size of 124 nm measured by a Malvern LoC apparatus.
  • an aqueous dispersion containing 3% of dry extract is prepared by diluting a part of the product obtained with deionized water (for example, 38 g of 27.6% latex). of dry extract diluted with 312 g of demineralised water). The pH of the diluted latex is then 3.5, measured by potentiometry and its viscosity is very close to that of water. A 36% sodium hydroxide solution is then added slowly and with stirring of the latex, so as to obtain the alkaline swelling and the thickening effect.
  • the maximum viscosity is obtained at a pH of 7.4, at which the 3% dispersion takes the form of a translucent, substantially transparent aqueous gel having a viscosity of 8826 mPa.s at 30 rpm measured with a viscometer Brookfield variable speed.
  • the gel has, in addition, colored reflections ranging from red to blue through green, depending on the viewing angle.
  • the synthesis of this can be done in the wake of that of the surfactant polymer of Example 2.
  • the total amount of product of the Example 2 can be adjusted to have only 303 g and the holding step at 50 ° C after addition of the monomers of Example 2 can be limited to a minimum of 1 or 2 hours, after which the reactor can to be brought to 78 ° C for the sequence of the operations of Example 3.
  • the synthesis of the water-soluble initiator of Example 1 can be carried out in the polymerization reactor, by adjusting the dilution ratio with water and a small amount of alcohol. ethyl, as well as the amounts of sodium 4-styrene sulfonate and alkoxyamine (Ia), so as to obtain only the amount of water-soluble initiator (II) necessary for the preparation of the surfactant of Example 2.
  • the time of Heating at 70 ° C. for the preparation of the water-soluble initiator can be optimized by changing it to a minimum of 1 hour, after which time the operations of Example 4 can be chained.
  • this method does not require the separation and / or purification of the initiator (II) or its manipulation in the form of wax, because it is produced directly in the polymerization reactor (in dilute solution and in the necessary amount), in which it will be used for the manufacture of the polymeric surfactant which will serve, for its part, to the manufacture of the final ASE latex.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • Wood Science & Technology (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polymerisation Methods In General (AREA)
  • Polymerization Catalysts (AREA)
  • Paints Or Removers (AREA)
EP07726611A 2006-03-02 2007-03-02 Utilisation de polymeres ou copolymeres particuliers en tant qu'agent tensio-actif pour la stabilisation de latex Withdrawn EP1989257A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0601876A FR2898129B1 (fr) 2006-03-02 2006-03-02 Utilisation de polymeres ou copolymeres particuliers en tant qu'agent tensio-actif pour la stabilisation de latex
PCT/EP2007/052017 WO2007099168A1 (fr) 2006-03-02 2007-03-02 Utilisation de polymeres ou copolymeres particuliers en tant qu'agent tensio-actif pour la stabilisation de latex

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EP1989257A1 true EP1989257A1 (fr) 2008-11-12

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EP07726611A Withdrawn EP1989257A1 (fr) 2006-03-02 2007-03-02 Utilisation de polymeres ou copolymeres particuliers en tant qu'agent tensio-actif pour la stabilisation de latex

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Country Link
US (1) US20090170958A1 (pt)
EP (1) EP1989257A1 (pt)
JP (1) JP2009528419A (pt)
KR (1) KR20080112243A (pt)
CN (1) CN101405338A (pt)
BR (1) BRPI0708465A2 (pt)
FR (1) FR2898129B1 (pt)
WO (1) WO2007099168A1 (pt)

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FR2969665B1 (fr) * 2010-12-23 2013-09-13 Arkema France Particules polymeriques filamenteuses et leur utilisation comme modificateurs de rheologie
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FR2814170B1 (fr) * 2000-09-18 2005-05-27 Rhodia Chimie Sa Nouveau latex a proprietes de surface modifiees par l' ajout d'un copolymere hydrosoluble a caractere amphiphile
FR2843394B1 (fr) * 2002-08-07 2005-12-30 Atofina Alcoxyamines issues de nitroxydes b-phosphore, leur utilisation en polymerisation radicalaire
FR2848557B1 (fr) * 2002-12-13 2006-07-07 Atofina Copolymeres a gradient solubles ou du moins dispersibles dans l'eau comme dans les solvants organiques
FR2866026B1 (fr) * 2004-02-06 2008-05-23 Arkema Procede de polymerisation radicalaire en emulsion mettant en oeuvre des alcoxyamines hydrosolubles

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FR2898129B1 (fr) 2008-05-09
KR20080112243A (ko) 2008-12-24
FR2898129A1 (fr) 2007-09-07
JP2009528419A (ja) 2009-08-06
US20090170958A1 (en) 2009-07-02
WO2007099168A1 (fr) 2007-09-07
BRPI0708465A2 (pt) 2011-05-31
CN101405338A (zh) 2009-04-08

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