WO2011104599A1 - Monomere associatif a base d'alcools oxo, polymere acrylique contenant ce monomere, utilisation dudit polymere comme epaississant dans une formulation aqueuse, formulation obtenue - Google Patents
Monomere associatif a base d'alcools oxo, polymere acrylique contenant ce monomere, utilisation dudit polymere comme epaississant dans une formulation aqueuse, formulation obtenue Download PDFInfo
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- WO2011104599A1 WO2011104599A1 PCT/IB2011/000327 IB2011000327W WO2011104599A1 WO 2011104599 A1 WO2011104599 A1 WO 2011104599A1 IB 2011000327 W IB2011000327 W IB 2011000327W WO 2011104599 A1 WO2011104599 A1 WO 2011104599A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
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- 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
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- 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
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- 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
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
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- 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
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- 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
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- 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
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
- C08F220/286—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety and containing polyethylene oxide in the alcohol moiety, e.g. methoxy polyethylene glycol (meth)acrylate
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- 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
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
- C08F220/288—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety and containing polypropylene-co-ethylene oxide in the alcohol moiety
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- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
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- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/02—Emulsion paints including aerosols
- C09D5/024—Emulsion paints including aerosols characterised by the additives
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- 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
- C09D7/43—Thickening agents
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- 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
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
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- 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
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
Definitions
- the present invention relates to novel rheology modifiers of the HASE type, the associative monomer of which is functionalized by a hydrophobic group based on oxo alcohols.
- these products lead to a phenomenon of increase of the viscosity over a wide range of shear gradients, and especially for high gradients: they behave therefore as effective thickeners, and as such constitute a new range of products that enriches the library of the paint formulator.
- these new thickeners can develop, when introduced into an aqueous formulation, much more Newtonian rheological profiles than their predecessors HASE type, and maintaining a level of efficiency economically interesting.
- Such a result is obtained by the implementation of the particular associative monomers mentioned above. This property is even exacerbated in a preferred embodiment which consists in adjusting in a certain range the dose of chain transfer agent used in the process for manufacturing said polymers.
- the associative monomers functionalized with hydrophobic groups based on oxo alcohols constitute an object of the present invention.
- the use of these as thickeners in aqueous formulations and the resulting formulations constitute the latter two objects of the present invention.
- HEUR Hydrophobically Modified Ethylene Oxide Ethethexide Modified Ethylene Oxide URethane according to the appropriate acronym
- HASE hydrophobically modified and thickening modified Emulsions in an alkaline medium or Hydrophobically modified Alkali -soluble Emulsions.
- the former denote polymers resulting from the synthesis between a polyalkylene glycol compound, a polyisocyanate, and an alkyl and / or aryl associative monomer consisting of a hydrophobic end group.
- the second are polymers of (meth) acrylic acid, an ester of these acids and an associative monomer consisting of an oxyalkylated chain terminated by a hydrophobic group.
- HEURs are at the origin of many properties in aqueous paints, in particular depending on the nature of their associative monomer.
- EP 0 639 595 A1 which proposes hydrophobic groups having from 4 to 36 carbon atoms for increasing the Brookfield TM viscosity
- WO 02/102868 A1 which describes the use of plurystyrylphenols with more than 40 atoms to increase the viscosity irrespective of the shear gradient
- an associative monomer consisting of di- and tristyrylphenol making it possible to obtain excellent pigment compatibility and high viscosity. low and medium shear rate.
- a “Newtonian” profile theoretically means that the viscosity remains independent of the shear gradient: such behavior is inaccessible in reality.
- a person skilled in the art associates such a profile with a small change in viscosity as a function of the shear rate (rheogram all the more flat), as opposed to a pseudo-plastic profile characterized by a marked drop in viscosity. according to this gradient (rheogram all the more steep).
- the higher the ratio between the Brookfield viscosity at 10 rpm in mPa.s and the cone-plane viscosity called "ICI" approximately corresponding to a speed gradient of 10,000 s " ) is weak, the closer we get to a Newtonian behavior.
- HEUR are chemical species that are difficult to dissolve in water and must be dissolved in the presence of solvents or surfactants, since their% of active ingredient exceeds about 25%, and as long as they develop Newtonian profiles.
- This problem is recounted in EP 0 682 094 A1: the solution proposed is based trivially on the use of surfactants.
- HEUR thickeners highly concentrated and containing surfactants, had been marketed by COATEX under the names COAPUR TM 5035 and COAPUR TM 6050, before the priority date of this application, and as soon as possible. 1993 for the first of them.
- solvents and surfactants to formulate the thickener type HEUR is not without posing a number of problems.
- these new thickeners make it possible to develop particularly marked Newtonian profiles, particularly in terms of ratio (Brookfield viscosity at 10 rpm in mPa.s / viscosity ICI), while maintaining a high ICI viscosity;
- n and n are integers less than 150, at least one of which is non-zero,
- a and B denote alkyl groups different from each other, and having from 2 to
- the group AO preferably denoting ethylene oxide and the group BO preferably denoting propylene oxide,
- R denotes a polymerizable unsaturated functional group, preferentially methacrylate
- R ' being characterized in that it consists of at least one group of formula (II):
- One of the keys of the present invention rests on the choice of the compounds of formula (II), as terminal hydrophobic group of the associative monomer of formula (I).
- the latter is conventionally manufactured by ethoxylation of an alcohol, then functionalization to make it polymerizable.
- the Applicant has noted that the particular choice of an oxo alcohol allows the synthesis of new associative monomers of formula (I), which ultimately confer all of the properties listed above.
- a first subject of the invention consists of a monomer of formula (I):
- n and n are integers less than 150, at least one of which is non-zero,
- a and B denote alkyl groups different from each other, and having from 2 to
- the group AO preferably denoting ethylene oxide and the group BO preferably denoting propylene oxide,
- R denotes a polymerizable unsaturated functional group, preferentially methacrylate, R 'being characterized in that it consists of at least one group of formula (II):
- a second subject of the present invention consists of a polymer of the HASE type, consisting of: a) (meth) acrylic acid,
- This polymer is also characterized in that it is constituted, expressed in% by weight of each of its monomers: a) from 20% to 50%, preferably from 35% to 45% of (meth) acrylic acid, b) from 40% to 70%, preferably from 45% to 55% of at least one ester of (meth) acrylic acid,
- a third object of the The present invention consists of a process for manufacturing a HASE-type polymer, by placing in contact in a reaction medium between: a) (meth) acrylic acid,
- said process is characterized in that the transfer agent is used and in that its mass introduced into the reaction medium is between 1500 ppm and 4000 ppm relative to the total weight of the components a ), b) and c). Quite unexpectedly, the Newtonian character of the rheological profile induced by the polymer in water is improved, while maintaining a high thickening efficiency with a high shear rate.
- This process is also characterized in that the chain transfer agent is chosen from N-dodecyl mercaptan, N-decyl mercaptan, octyl mercaptan, 1,8-dimercapto-3,6-dioxaoctane (DMDO, CAS No. 14970-87-7), thiolactic acid.
- the chain transfer agent is chosen from N-dodecyl mercaptan, N-decyl mercaptan, octyl mercaptan, 1,8-dimercapto-3,6-dioxaoctane (DMDO, CAS No. 14970-87-7), thiolactic acid.
- a fourth object of the present invention is the use of a HASE type polymer as previously explained as a thickening agent in an aqueous formulation.
- a fifth and final object of the present invention is an aqueous formulation containing a HASE type polymer as previously explained, including an aqueous paint formulation.
- Example 1 This test illustrates the implementation of associative thickeners according to the prior art (HASE) and according to the invention, for the purpose of thickening an aqueous gel.
- This test illustrates the prior art and uses a HASE type associative thickener marketed by COATEX TM under the name Rheotech TM 2100.
- This thickener contains alkylphenols.
- HASE associative thickener which is a polymer consisting of, in% by weight of each of its monomers: a) 35.5% of methacrylic acid,
- a pre-emulsion is prepared by weighing in a beaker: 116.8 grams of bi-permuted water,
- HASE associative thickener which is a polymer consisting of, in% by weight of each of its monomers: a) 35.5% of methacrylic acid,
- This monomer was obtained by ethoxylation of the commercial product Liai 123, then rendered polymerizable by functionalization using a methacrylate group.
- the ethoxylation is carried out by methods well known to those skilled in the art. It is the same for functionalization.
- This polymer was obtained by bringing into contact in a reaction medium which is water, all of the aforementioned monomers and this, in the presence of 560 ppm of a chain transfer agent which is dodecyl mercaptan.
- HASE associative thickener which is a polymer consisting of, in% by weight of each of its monomers: a) 35.5% of methacrylic acid,
- This monomer was obtained by ethoxylation of the commercial product Liai 123, then rendered polymerizable by functionalization using a methacrylate group.
- the ethoxylation is carried out by methods well known to those skilled in the art. It is the same for functionalization.
- This polymer was obtained by bringing into contact in a reaction medium which is water, all of the aforementioned monomers and this, in the presence of 560 ppm of a chain transfer agent which is dodecyl mercaptan.
- HASE associative thickener which is a polymer consisting of, in% by weight of each of its monomers: a) 34.0% of methacrylic acid,
- This monomer was obtained by ethoxylation of the commercial product Liai 123, then rendered polymerizable by functionalization using a methacrylate group.
- the ethoxylation is carried out by methods well known to those skilled in the art. It is the same for functionalization.
- This polymer was obtained by bringing into contact in a reaction medium which is water, all of the aforementioned monomers and this, in the presence of 560 ppm of a chain transfer agent which is dodecyl mercaptan.
- the performance of the Rheotech TM 2100 product containing alkyl phenols is at least equal, and is greatly improved in the context of the ICI viscosity.
- Example 2 This test illustrates the implementation of associative thickeners according to the invention, for the purpose of thickening an aqueous gel. It illustrates in particular the influence of the amount of chain transfer agent used during the synthesis of said thickener.
- HASE associative thickener which is a polymer consisting of, in% by weight of each of its monomers: a) 35.5% of methacrylic acid,
- This polymer was obtained by bringing into contact in a reaction medium which is water, all of the aforementioned monomers and this, in the presence of 1392 ppm of a chain transfer agent which is dodecyl mercaptan.
- This test illustrates the invention and implements an associative thickener type HASE according to the invention, which is the same polymer as that used in test No. 8.
- This polymer was obtained by contacting in a reaction medium which is water, all of the aforementioned monomers and this, in the presence of 1944 ppm of a chain transfer agent which is dodecyl mercaptan.
- This test illustrates the invention and uses a HASE associative thickener according to the invention, which is the same polymer as that used in test No. 8.
- This polymer was obtained by contacting in a reaction medium which is water, all of the aforementioned monomers and this, in the presence of 2840 ppm of a chain transfer agent which is dodecyl mercaptan.
- This test illustrates the invention and implements an associative thickener type HASE according to the invention, which is the same polymer as that used in test No. 8.
- This polymer was obtained by contacting in a reaction medium which is water, all of the aforementioned monomers and this, in the presence of 4160 ppm of a chain transfer agent which is dodecyl mercaptan.
- This test illustrates the invention and implements an associative thickener type HASE according to the invention, which is the same polymer as that used in test No. 8.
- This polymer was obtained by contacting in a reaction medium which is water, all of the aforementioned monomers and this, in the presence of 5600 ppm of a chain transfer agent which is dodecyl mercaptan.
- Brookfield TM viscosities at 10 and 100 rpm, Stormer TM and ICI TM, as well as the ratio of Brookfield TM viscosity at 10 rpm and ICI TM viscosity were reported in Table 2.
- This test illustrates the invention, does not implement chain transfer agent, and relates to an aqueous emulsion of a polymer consisting of, in% by weight of each of its monomers: a) 35.5% of methacrylic acid,
- This polymer was obtained by bringing into contact in a reaction medium which is water, all of the aforementioned monomers. Its synthesis corresponds to that described in tests No. 14 to 19, but without the use of chain transfer agent.
- each of these fully pre-eutralised emulsions makes it possible to effectively thicken the acrylic binder solution (Table 5).
- Table 5 The best results are obtained in particular according to the emulsions of tests Nos. 17 and 18 which, while having a Brookfield TM viscosity at 10 rpm less than 20,000 mPa.s for an extract however 25% dry, nevertheless lead to a significant thickening, regardless of the shear gradient.
- pre-eutralised emulsions of the HASE type are available, which are stable and can be handled for a dry extract of commercial interest, devoid of nonyl phenols, and which can advantageously thicken a latex in aqueous solution.
- a chain transfer agent which is dodecyl mercaptan, and relates to an aqueous emulsion of a polymer consisting of, in% by weight of each of its monomers:
- This test illustrates the invention. It implements in particular an associative monomer different from that used in the previous tests (similar to that used in tests No. 14 to 19, but oxyethylated 25 times, the% of the associative monomer here being 10 and 15%).
- This polymer was obtained by bringing into contact in a reaction medium which is water, all of the aforementioned monomers, according to the same procedure as previously described.
- pre-eutralised emulsions of the HASE type are available, which are stable and can be handled for a dry extract of commercial interest, devoid of nonyl phenols, and which can advantageously thicken a latex in aqueous solution.
- tests illustrate areas outside the invention. They implement in particular an associative monomer different from that used in the previous tests, and free of nonylphenols. They put (tests 25 to 27) or not (tests 23 and 24) implemented 2 110 ppm of a chain transfer agent which is dodecyl mercaptan.
- Tests No. 23 to 27 do not lead to preneutralized emulsions and can be handled as they are at a solids content of 20%; they could not be tested on the acrylic binder.
- This test illustrates a field outside the invention and uses an emulsion of a HASE polymer marketed by COATEX TM under the name Rheotech TM 2100, which contains nonylphenols.
- this emulsion contains nonylphenols.
- Brookfield TM viscosities at 10 and 100 rpm Brook 10T, Brook 100T mpas
- Stormer TM in KU
- ICI TM the ratio of Brookfield TM viscosity at 10 rpm to viscosity ICI TM have been reported in Table 6.
- the performance of the Rheotech TM 2100 product containing alkyl phenols is at least equal, and is greatly improved in the context of the ICI viscosity.
- Example 5 This test illustrates the implementation of associative thickeners according to the prior art (HASE) and according to the invention, for the purpose of thickening an aqueous gel.
- Brookfield TM viscosities at 10 and 100 rpm Brook 10T, Brook 100T mpas
- Stormer TM in KU
- ICI TM the ratio of Brookfield TM viscosity at 10 rpm to viscosity ICI TM have been reported in Table 7.
- the performance of the Rheotech TM 2100 product containing alkyl phenols is at least equal, and is greatly improved in the context of the ICI viscosity.
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- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
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- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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Abstract
Description
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Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2011219565A AU2011219565B2 (en) | 2010-02-26 | 2011-02-17 | Associative monomer based on oxo alcohols, acrylic polymer containing this monomer, use of said polymer as thickener in an aqueous formulation, and formulation obtained |
BR112012021420A BR112012021420A2 (pt) | 2010-02-26 | 2011-02-17 | monômero,polímero do tipo hase, processo de fabricação de um polímero do tipo hase, uso de um polímero do tipo hase, e, formulação aquosa contendo um polímero do tipo hase. |
EP11714392.5A EP2539311B1 (fr) | 2010-02-26 | 2011-02-17 | Monomere associatif a base d'alcools oxo, polymere acrylique contenant ce monomere, utilisation dudit polymere comme epaississant dans une formulation aqueuse, formulation obtenue |
ES11714392.5T ES2614081T3 (es) | 2010-02-26 | 2011-02-17 | Monómero asociativo a base de alcoholes oxo, polímero acrílico que contiene este monómero, uso de dicho polímero como espesante en una formulación acuosa, y la formulación obtenida |
RU2012140943/04A RU2583431C2 (ru) | 2010-02-26 | 2011-02-17 | Ассоциативный мономер на основе оксо-спиртов, акриловый полимер, содержащий этот мономер, применение указанного полимера в качестве загустителя в водном составе, полученный состав |
CN201180010815.2A CN102770406B (zh) | 2010-02-26 | 2011-02-17 | 基于羰基合成醇的缔合单体、包含该单体的丙烯酸类聚合物、所述聚合物在水性制剂中作为增稠剂的用途、以及所得制剂 |
DK11714392.5T DK2539311T3 (en) | 2010-02-26 | 2011-02-17 | Associative monomer based on oxo alcohols, acrylic polymer with this monomer, use of this polymer as a thickener in an aqueous formulation and obtained formulation |
JP2012554431A JP6254346B2 (ja) | 2010-02-26 | 2011-02-17 | オキソ・アルコールベースの結合性モノマーと、このモノマーを含むポリマーと、水溶性配合組成物でのこのポリマーの増粘剤としての使用と、得られた配合組成物 |
CA2788447A CA2788447A1 (fr) | 2010-02-26 | 2011-02-17 | Monomere associatif a base d'alcools oxo, polymere acrylique contenant ce monomere, utilisation dudit polymere comme epaississant dans une formulation aqueuse, formulation obtenue |
MX2012009849A MX341525B (es) | 2010-02-26 | 2011-02-17 | Monomero asociativo a base de alcoholes oxo, polimero acrilico que contiene este monomero, uso de dicho polimero como espesante en una formulacion acuosa, formulacion obtenida. |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1051366A FR2956862B1 (fr) | 2010-02-26 | 2010-02-26 | Monomere associatif a base d'alcools oxo, polymere acrylique contenant ce monomere, utilisation dudit polymere comme epaississant dans une formulation aqueuse, formulation obtenue. |
FR1051366 | 2010-02-26 | ||
US31475410P | 2010-03-17 | 2010-03-17 | |
US61/314,754 | 2010-03-17 |
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US (1) | US8791199B2 (fr) |
EP (1) | EP2539311B1 (fr) |
JP (1) | JP6254346B2 (fr) |
KR (1) | KR101565530B1 (fr) |
CN (2) | CN105237690B (fr) |
AU (1) | AU2011219565B2 (fr) |
BR (1) | BR112012021420A2 (fr) |
CA (1) | CA2788447A1 (fr) |
DK (1) | DK2539311T3 (fr) |
ES (1) | ES2614081T3 (fr) |
FR (1) | FR2956862B1 (fr) |
HU (1) | HUE030320T2 (fr) |
MX (1) | MX341525B (fr) |
PL (1) | PL2539311T3 (fr) |
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Cited By (7)
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WO2014096622A1 (fr) | 2012-12-20 | 2014-06-26 | Coatex | Microparticules d'agent actif |
CN104039886A (zh) * | 2011-11-18 | 2014-09-10 | 可泰克斯公司 | 含有烷基环己醇烷氧基化物的离子缔合型增稠剂、其用途以及包含该增稠剂的制剂 |
WO2016132027A1 (fr) | 2015-02-18 | 2016-08-25 | Coatex | Microparticules polymeriques |
FR3130502A1 (fr) | 2021-12-21 | 2023-06-23 | Melchior Material And Life Science France | Composition agrochimique pour enrobage de graines |
WO2023175279A1 (fr) | 2022-03-16 | 2023-09-21 | Melchior Material And Life Science France | Formulations de pheromones encapsulees resistantes aux rayonnements lumineux |
FR3133522A1 (fr) | 2022-03-16 | 2023-09-22 | Melchior Material And Life Science France | Formulations de pheromones encapsulees resistantes aux rayonnements lumineux |
WO2023194695A1 (fr) | 2022-04-07 | 2023-10-12 | Melchior Material And Life Science France | Procede biologique de lutte contre les insectes piqueurs |
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FR2950061B1 (fr) * | 2009-09-11 | 2013-12-20 | Coatex Sas | Monomeres associatifs a base de polycosanols, epaississants associatifs correspondants et leurs utilisations |
FR2982266B1 (fr) * | 2011-11-04 | 2015-02-20 | Coatex Sas | Emulsion d'un polymere acrylique associatif polymerise en presence de polyglycerols et son utilisation comme agent epaississant dans une formulation aqueuse. |
FR2982263B1 (fr) | 2011-11-04 | 2015-03-27 | Coatex Sas | Epaississant acrylique associatif contenant des polyglycerols et son utilisation pour augmenter le temps ouvert de films minces ou epais. |
FR3003264B1 (fr) | 2013-03-18 | 2016-12-09 | Coatex Sas | Utilisation d'une emulsion polymerique pour traiter en surface des particules de matiere minerale. |
FR3032716B1 (fr) | 2015-02-17 | 2017-02-24 | Bostik Sa | Colle contact de polychloroprene a base aqueuse |
FR3056983B1 (fr) * | 2016-09-30 | 2020-05-22 | Coatex | Copolymere anionique epaississant |
FR3057867B1 (fr) * | 2016-10-25 | 2018-11-02 | Coatex | Preparation d'emulsion polymerique |
WO2018206195A1 (fr) | 2017-05-10 | 2018-11-15 | Basf Se | Polymère à structure ramifiée |
US11832610B2 (en) | 2018-04-27 | 2023-12-05 | Dow Global Technologies Llc | Rheological modifiers for spray drift control in agrochemical emulsions |
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- 2011-02-17 CA CA2788447A patent/CA2788447A1/fr not_active Abandoned
- 2011-02-17 MX MX2012009849A patent/MX341525B/es active IP Right Grant
- 2011-02-17 ES ES11714392.5T patent/ES2614081T3/es active Active
- 2011-02-17 AU AU2011219565A patent/AU2011219565B2/en not_active Ceased
- 2011-02-17 EP EP11714392.5A patent/EP2539311B1/fr active Active
- 2011-02-17 BR BR112012021420A patent/BR112012021420A2/pt not_active Application Discontinuation
- 2011-02-17 WO PCT/IB2011/000327 patent/WO2011104599A1/fr active Application Filing
- 2011-02-17 CN CN201510641485.7A patent/CN105237690B/zh active Active
- 2011-02-17 KR KR1020127022022A patent/KR101565530B1/ko active IP Right Grant
- 2011-02-17 CN CN201180010815.2A patent/CN102770406B/zh active Active
- 2011-02-17 PL PL11714392T patent/PL2539311T3/pl unknown
- 2011-02-17 DK DK11714392.5T patent/DK2539311T3/en active
- 2011-02-17 RU RU2012140943/04A patent/RU2583431C2/ru active
- 2011-02-17 JP JP2012554431A patent/JP6254346B2/ja active Active
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Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104039886A (zh) * | 2011-11-18 | 2014-09-10 | 可泰克斯公司 | 含有烷基环己醇烷氧基化物的离子缔合型增稠剂、其用途以及包含该增稠剂的制剂 |
CN104039886B (zh) * | 2011-11-18 | 2016-11-23 | 可泰克斯公司 | 含有烷基环己醇烷氧基化物的离子缔合型增稠剂、其用途以及包含该增稠剂的制剂 |
WO2014096622A1 (fr) | 2012-12-20 | 2014-06-26 | Coatex | Microparticules d'agent actif |
WO2016132027A1 (fr) | 2015-02-18 | 2016-08-25 | Coatex | Microparticules polymeriques |
FR3130502A1 (fr) | 2021-12-21 | 2023-06-23 | Melchior Material And Life Science France | Composition agrochimique pour enrobage de graines |
WO2023118751A1 (fr) | 2021-12-21 | 2023-06-29 | Melchior Material And Life Science France | Composition agrochimique pour enrobage de graines |
WO2023175279A1 (fr) | 2022-03-16 | 2023-09-21 | Melchior Material And Life Science France | Formulations de pheromones encapsulees resistantes aux rayonnements lumineux |
FR3133522A1 (fr) | 2022-03-16 | 2023-09-22 | Melchior Material And Life Science France | Formulations de pheromones encapsulees resistantes aux rayonnements lumineux |
FR3133521A1 (fr) | 2022-03-16 | 2023-09-22 | Melchior Material And Life Science France | Formulations de pheromones encapsulees resistantes aux rayonnements lumineux |
WO2023194695A1 (fr) | 2022-04-07 | 2023-10-12 | Melchior Material And Life Science France | Procede biologique de lutte contre les insectes piqueurs |
FR3134285A1 (fr) | 2022-04-07 | 2023-10-13 | Melchior Material And Life Science France | Procede biologique de lutte contre les insectes piqueurs |
Also Published As
Publication number | Publication date |
---|---|
FR2956862B1 (fr) | 2013-03-15 |
CN102770406B (zh) | 2015-10-07 |
CN102770406A (zh) | 2012-11-07 |
KR20120107523A (ko) | 2012-10-02 |
KR101565530B1 (ko) | 2015-11-13 |
PL2539311T3 (pl) | 2017-03-31 |
CN105237690B (zh) | 2018-03-20 |
AU2011219565B2 (en) | 2016-06-30 |
PT2539311T (pt) | 2016-12-23 |
DK2539311T3 (en) | 2017-01-30 |
HUE030320T2 (hu) | 2017-05-29 |
US8791199B2 (en) | 2014-07-29 |
AU2011219565A1 (en) | 2012-08-30 |
US20110213072A1 (en) | 2011-09-01 |
ES2614081T3 (es) | 2017-05-29 |
RU2583431C2 (ru) | 2016-05-10 |
MX2012009849A (es) | 2012-09-21 |
CA2788447A1 (fr) | 2011-09-01 |
BR112012021420A2 (pt) | 2016-05-24 |
CN105237690A (zh) | 2016-01-13 |
JP6254346B2 (ja) | 2017-12-27 |
JP2013520546A (ja) | 2013-06-06 |
EP2539311A1 (fr) | 2013-01-02 |
EP2539311B1 (fr) | 2016-11-02 |
RU2012140943A (ru) | 2014-04-10 |
FR2956862A1 (fr) | 2011-09-02 |
MX341525B (es) | 2016-08-24 |
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