Classifications

• • 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
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/08—Processes
  • C08G18/16—Catalysts
  • C08G18/22—Catalysts containing metal compounds
  • C08G18/227—Catalysts containing metal compounds of antimony, bismuth or arsenic
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/2805—Compounds having only one group containing active hydrogen
  • C08G18/2815—Monohydroxy compounds
  • C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/48—Polyethers
  • C08G18/4833—Polyethers containing oxyethylene units
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/72—Polyisocyanates or polyisothiocyanates
  • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/72—Polyisocyanates or polyisothiocyanates
  • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
  • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
  • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
  • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
  • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
  • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/32—Polymers modified by chemical after-treatment
  • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
  • C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
  • C08G65/33348—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing isocyanate group
  • C08G65/33351—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing isocyanate group acyclic
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/32—Polymers modified by chemical after-treatment
  • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
  • C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
  • C08G65/33348—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing isocyanate group
  • C08G65/33355—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing isocyanate group cyclic
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/32—Polymers modified by chemical after-treatment
  • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
  • C08G65/337—Polymers modified by chemical after-treatment with organic compounds containing other elements
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
  • C08G65/48—Polymers modified by chemical after-treatment
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
  • C08L71/02—Polyalkylene oxides
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
  • C08L75/04—Polyurethanes
  • C08L75/08—Polyurethanes from polyethers
• • 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
  • C09D125/00—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 an aromatic carbocyclic ring; Coating compositions based on derivatives of such polymers
  • C09D125/02—Homopolymers or copolymers of hydrocarbons
  • C09D125/04—Homopolymers or copolymers of styrene
  • C09D125/08—Copolymers of styrene
  • C09D125/14—Copolymers of styrene with unsaturated 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
  • C09D17/00—Pigment pastes, e.g. for mixing in paints
  • C09D17/001—Pigment pastes, e.g. for mixing in paints in aqueous medium
• • 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
• • 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
  • C09D7/65—Additives macromolecular

Definitions

• the invention relates to a difunctional rheology modifying compound.
• the invention also provides an aqueous composition comprising a difunctional compound according to the invention as well as a method for controlling the viscosity of an aqueous composition by means of the difunctional compound according to the invention.
• aqueous coating compositions and in particular for aqueous paint or varnish compositions, it is necessary to control the viscosity both for low or medium shear gradients and for high shear gradients.
• a paint formulation undergoes many constraints requiring particularly complex rheological properties.
• the pigment particles tend to settle by gravity. Stabilizing the dispersion of these pigment particles then requires having a paint formulation whose viscosity is high at very low shear gradients corresponding to the limit speed of the particles. Paint pick-up is the amount of paint carried away by means of an application tool, such as a brush, brush or roller for example.
• Paint pick-up is an increasing function of viscosity.
• the equivalent shear rate calculation is a function of the paint flow rate for a particular thickness of paint on the tool.
• the paint formulation should therefore also have a high viscosity at low or medium shear rates.
• a high filling power of the paint must be sought so that when it is applied to a substrate, a large quantity of paint is deposited during each pass. A high filling power then makes it possible to obtain a greater wet film during each pass of the tool.
• a high viscosity of the paint formulation must therefore be sought at high shear rates. High viscosity at high shear rates will also reduce or eliminate the risk of spattering or dripping during paint application. A reduced viscosity at low or medium shear gradients will also make it possible to obtain a good taut appearance after application of the paint, in particular a single-coat paint, on a substrate whose coated surface will then present a very regular appearance, without bumps or hollow. The final visual appearance of the dry film is then much better.
• the paint after being deposited on a surface, in particular a vertical surface, the paint should not form a run. It is then necessary for the paint formulation to have a high viscosity at low and medium shear rates.
• the paint should have a significant leveling capacity. Reduced viscosity at low to medium shear rates of the paint formulation is then required.
• EP0761779 EP0761780 describe thickening and heat-resistant diurethane compounds.
• CA1341003 discloses polyethoxylated and polypropoxylated diurethane compounds.
• Document LR2113316 discloses diurethane compounds for textile printing paste.
• JPH11228686 discloses certain compounds prepared by reaction of halides and aromatic compounds.
• the document WO9631550 describes poly(acetal-polyether) compounds prepared from a dibromo compound and a polyol.
• Compounds of the HEUR type hydrophobically modified ethoxylated urethanes or ethoxylated and hydrophobically modified urethanes
• rheology modifying agents are known as rheology modifying agents.
• the known HEUR-type compounds do not always make it possible to provide a satisfactory solution.
• the rheology modifying compounds of the state of the art do not always allow effective control of the viscosity or do not always allow the compromise between Stormer viscosity (measured at low or medium shear gradients and expressed in KU units) and ICI viscosity (measured at high or very high shear rates and expressed in s 1 ).
• the known rheology modifier compounds do not always make it possible to increase the ICI viscosity/Stormer viscosity ratio.
• the difunctional compound according to the invention makes it possible to provide a solution to all or part of the problems of the rheology modifying agents of the state of the art.
• the invention provides a difunctional compound T prepared by reacting: a. of a molar equivalent of at least one reactive compound (a) chosen from:
• - monoaromatic monoalcohols (b4) comprising from 6 to 30 polyethoxylated carbon atoms comprising from 80 to 500 ethoxylated groups
• - polyaromatic monoalcohols (b5) comprising from 10 to 80 polyethoxylated carbon atoms comprising from 80 to 500 oxyethylene groups.
• the difunctional compound T is prepared from at least one compound (al) comprising two isocyanate groups or from at least one compound (a2) comprising two atoms of halogen and a compound (b) capable of reacting with these isocyanate groups and comprising a hydrocarbon chain - saturated, unsaturated or aromatic - combined with a polyethoxylated chain.
• this reactive compound (b) is a monohydroxylated compound.
• the condensation of the compounds (al) and (b) is carried out in the presence of a catalyst.
• This catalyst can be chosen from an amine, preferably 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), a derivative of a metal chosen from Al, Bi, Sn, Hg, Pb, Mn, Zn, Zr, Ti. Traces of water can also participate in the catalysis of the reaction.
• DBU 1,8-diazabicyclo[5.4.0]undec-7-ene
• metal derivatives a derivative selected from dibutyl bismuth dilaurate, dibutyl bismuth diacetate, dibutyl bismuth oxide, bismuth carboxylate, dibutyl tin dilaurate, dibutyl tin diacetate, dibutyl tin oxide, a derivative of mercury is preferred.
• a derivative of lead zinc salts, manganese salts, a compound comprising chelated zirconium, a compound comprising chelated aluminium.
• the preferred metal derivative is chosen from a derivative of Bi, a derivative of S n and a derivative of Ti.
• the condensation of the compounds (a2) and (b) is carried out in the presence of a catalyst, in particular a basic catalyst.
• a catalyst in particular a basic catalyst.
• This catalyst can be chosen from strong bases such as KOH, NaOH.
• the reaction implements a single compound (a) or else the reaction implements two or three different compounds (a).
• the polyisocyanate compound (al) comprises on average 2 isocyanate groups.
• the polyisocyanate compound (al) comprises on average 2 ⁇ 10 molar % isocyanate groups.
• the diisocyanate compounds are symmetrical diisocyanate compounds or else unsymmetrical diisocyanate compounds.
• Symmetrical diisocyanate compounds include two isocyanate groups that have the same reactivity.
• Unsymmetrical diisocyanate compounds include two isocyanate groups that have different reactivities.
• the compound (al) is chosen from:
• - symmetrical aromatic diisocyanate compounds preferably: * 2,2'-diphenylmethylene diisocyanate (2,2'-MDI) and 4,4'-diphenylmethylene diisocyanate (4,4'-MDI);
• H12MDI methylene bis(4-cyclohexylisocyanate)
• - symmetrical aliphatic diisocyanate compounds preferably hexamethylene diisocyanate (HDI), pentamethylene diisocyanate (PDI); unsymmetrical aromatic diisocyanate compounds, preferably:
• IPDI isophorone diisocyanate
• the compound (al) is chosen from IPDI, HDI, H12MDI and their combinations.
• the dihalogenated compound (a2) comprises on average 2 halogenated groups.
• the dihalogenated compound (a2) comprises on average 2 ⁇ 10% molar halogenated groups.
• the compound (a2) is a compound of formula (I) in which R independently represents Br or I, preferably Br. More preferably according to the invention, the compound (a2) is chosen from dibromomethane, diiodomethane and combinations thereof.
• monoalcohols are compounds comprising a single hydroxyl group (OH) which is terminal.
• the polyethoxylated monoalcohols are compounds comprising a hydrocarbon chain which comprises several ethoxylated groups and a terminal hydroxyl (OH) group.
• the polyethoxylated monoalcohols are compounds of formula Q-(LO) n -H in which Q represents a hydrocarbon chain, n represents the number of polyethoxylations and L, identical or different, independently represents a linear or branched alkylene group comprising from 1 to 4 carbon atoms.
• the non-alkoxylated monoalcohols are compounds comprising a hydrocarbon chain and a single terminal hydroxyl (OH) group.
• the non-alkoxylated monoalcohols are compounds of formula Q'-OH in which Q' represents a hydrocarbon chain.
• the number of carbon atoms defining the monoalcohols (b1) to (b5) therefore corresponds to the number of carbon atoms of the groups Q or Q'.
• the polyethoxylated monoalcohols comprise from 100 to 500 ethoxylated groups, preferably from 80 to 400 ethoxylated groups or from 100 to 200 ethoxylated groups.
• the polyethoxylated compounds (b) used may comprise a number of different ethoxylated groups.
• compound T is a compound comprising ethoxylated groups.
• the compound T has a degree of polyethoxylation which is strictly greater than 80 and up to 500 or else between 100 and 500 or between 100 and 502.
• the degree of polyethoxylation defines the number of ethoxylated groups included in this compound.
• compound (b) is such that:
• the hydrocarbon chain of the monoalcohol (bl) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 16 carbon atoms, more preferentially the monoalcohol (bl) is chosen from polyethoxylated n-octanol , polyethoxylated n-decanol, polyethoxylated n-dodecanol, polyethoxylated n-hexadecanol, or - the hydrocarbon chain of the monoalcohol (b2) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 16 carbon atoms carbon, more preferably the monoalcohol (b2) is chosen from polyethoxylated ethyl-hexanol, polyethoxylated iso-octanol, polyethoxylated iso-nonanol, polyethoxylated iso-decanol, polyethoxyl
• the hydrocarbon chain of the monoalcohol (b3) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 20 carbon atoms, more preferably the monoalcohol (b3) is chosen from polyethoxylated ethyl-cyclohexanol , polyethoxylated n-nonyl-cyclohexanol, polyethoxylated n-dodecyl-cyclohexanol, or
• the hydrocarbon chain of the monoalcohol (b4) comprises from 12 to 30 carbon atoms or from 12 to 22 carbon atoms, preferably the monoalcohol (b4) is chosen from polyethoxylated n-pentadodocecyl-phenol or
• the hydrocarbon chain of the monoalcohol (b5) comprises from 10 to 60 carbon atoms, preferably the monoalcohol (b5) is chosen from polyethoxylated naphthol, polyethoxylated distyryl-phenol, polyethoxylated tristyryl-phenol, polyethoxylated pentastyryl-cumyl-phenol.
• the compound T is prepared by means of a monoalcohol and in the absence of diol or triol or in the absence of a compound comprising at least two hydroxyl groups (OH).
• the invention also relates to a method for preparing this compound.
• the invention provides a method for preparing a difunctional compound T by reaction: a. of a molar equivalent of at least one reactive compound (a) chosen from:
• polyaromatic monoalcohols (b5) comprising from 10 to 80 polyethoxylated carbon atoms comprising from 80 to 500 ethoxylated groups.
• the condensation of the compounds (al) and (b) is carried out in the presence of a catalyst.
• the reaction is catalyzed by means of an amine, preferably by means of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), or at least one derivative of a metal selected from Al, Bi, Sn, Hg, Pb, Mn, Zn, Zr, Ti. Traces of water can also participate in the catalysis of the reaction.
• metal derivatives a derivative selected from dibutyl bismuth dilaurate, dibutyl bismuth diacetate, dibutyl bismuth oxide, bismuth carboxylate, dibutyl tin dilaurate, dibutyl tin diacetate, dibutyl tin oxide, a derivative of mercury, a derivative of lead, zinc salts, manganese salts, a compound comprising chelated zirconium, a compound comprising chelated aluminium.
• the preferred metal derivative is selected from a Bi derivative, an Sn derivative and a Ti derivative.
• the condensation of the compounds (a2) and (b) is carried out in the presence of a catalyst, in particular a basic catalyst.
• a catalyst in particular a basic catalyst.
• This catalyst can be chosen from strong bases such as KOH, NaOH.
• the condensation of compounds (a) and (b) is carried out in an organic solvent.
• the preferred organic solvents are solvents which are non-reactive with the isocyanate functions of the compound (a1) or else which are non-reactive with the halogen atoms of the compound (a2), in particular the solvents chosen from hydrocarbon solvents (in particular petroleum cuts Cs to C 30 ), aromatic solvents (in particular toluene and its derivatives) and their combinations.
• the condensation is carried out directly with the various reagents or else is carried out in toluene.
• a solution of the compound is obtained in an organic solvent.
• Such a solution can be implemented directly.
• the organic solvent can be separated and the compound T dried.
• Such a compound T according to the invention, which is dried, can then be implemented in solid form, for example in the form of powder or granules.
• the invention also relates to an aqueous composition comprising at least one difunctional compound T according to the invention.
• the invention also relates to a aqueous composition comprising at least one difunctional compound T prepared according to the preparation method according to the invention.
• the difunctional compound according to the invention is a compound having a hydrophilic character. It can be formulated in an aqueous medium.
• the aqueous composition according to the invention may also comprise at least one additive, in particular an additive chosen from:
• amphiphilic compound in particular a surface-active compound, preferably a hydroxylated surface-active compound, for example alkyl-polyalkyleneglycol, in particular alkyl-polyethyleneglycol and alkyl-polypropyleneglycol;
• a polysaccharide derivative for example cyclodextrin, cyclodextrin derivative, polyethers, alkyl-glucosides;
• solvents in particular coalescence solvents, and hydrotropic compounds, for example glycol, butylglycol, butyldiglycol, monopropyleneglycol, ethyleneglycol, ethylenediglycol, Dowanol products whose CAS number is 34590-94-8, Texanol products whose CAS number is 25265-77- 4;
• the invention also provides an aqueous formulation which can be used in many technical fields.
• the aqueous formulation according to the invention comprises at least one composition according to the invention and may comprise at least one organic or inorganic pigment or organic, organo-metallic or inorganic particles, for example calcium carbonate, talc, kaolin, mica, silicates , silica, metal oxides, in particular titanium dioxide, iron oxides.
• the aqueous formulation according to the invention may also comprise at least one agent chosen from a particle spacer, a dispersing agent, a steric stabilizing agent, an electrostatic stabilizing agent, an opacifying agent, a solvent, a coalescing agent, a antifoam, a preservative, a biocidal agent, a spreading agent, a thickening agent, a film-forming copolymer and mixtures thereof.
• at least one agent chosen from a particle spacer, a dispersing agent, a steric stabilizing agent, an electrostatic stabilizing agent, an opacifying agent, a solvent, a coalescing agent, a antifoam, a preservative, a biocidal agent, a spreading agent, a thickening agent, a film-forming copolymer and mixtures thereof.
• the formulation according to the invention can be implemented in numerous technical fields.
• the formulation according to the invention can be a coating formulation.
• the formulation according to the invention is an ink formulation, an adhesive formulation, a varnish formulation, a paint formulation, for example decorative paint or industrial paint.
• the formulation according to the invention is a paint formulation.
• the invention also provides a concentrated aqueous pigment paste comprising at least one difunctional compound T according to the invention or at least one difunctional compound T prepared according to the preparation method according to the invention and at least one organic or inorganic colored pigment.
• the difunctional compound according to the invention has properties allowing it to be used to modify or control the rheology of the medium comprising it.
• the invention also provides a method for controlling the viscosity of an aqueous composition.
• This viscosity control method according to the invention comprises the addition of at least one difunctional compound T according to the invention in an aqueous composition.
• This viscosity control method can also comprise the addition of at least one difunctional compound T prepared according to the preparation method according to the invention.
• the viscosity control method according to the invention is implemented by means of an aqueous composition according to the invention.
• the method for controlling the viscosity according to the invention is implemented by means of an aqueous formulation according to the invention.
• the preferred, particular or advantageous characteristics of the difunctional compound T according to the invention define aqueous compositions according to the invention, formulations according to the invention, pigment pastes and viscosity control methods which are also preferred, particular or advantageous. .
• Example 1 preparation of urethane compounds according to the invention
• Example 1-1 preparation of a compound T1 according to the invention
• reaction mixture is left under stirring for 60 minutes at 90°C ⁇ 1°C. Then, it is checked that the level of isocyanate is zero by a back dosing. 1 g of the reaction medium is taken, to which an excess of dibutylamine (1 molar for example) is added, which reacts with the isocyanate functions potentially present in the medium. Any unreacted dibutylamine is then dosed with hydrochloric acid (1 N for example). The quantity of isocyanate functions present in the reaction medium can then be deduced therefrom. If the latter is non-zero, the reaction is prolonged for periods of 15 minutes until the reaction is complete.
• the compound T1 obtained is formulated in water with the addition of 1000 ppm of a biocidal agent (Biopol SMV Chemipol) and 1000 ppm of an anti-foaming agent (Tego 1488 Evonik).
• a composition 1 consisting of 20% by weight of compound T1 according to the invention and 80% by weight of water is obtained.
• Example 1-2 preparation of a compound T2 according to the invention
• the reaction mixture is left under stirring for 60 minutes at 90°C ⁇ 1°C.
• the isocyanate content is zero by a back dosing. If the latter is non-zero, the reaction is prolonged for periods of 15 minutes until the reaction is complete.
• the compound T2 obtained is formulated in water with the addition of 1000 ppm of a biocidal agent (Biopol SMV Chemipol) and 1000 ppm of an antifoaming agent (Tego 1488 Evonik).
• a composition 2 consisting of 20% by weight of compound T2 according to the invention and 80% by weight of water.
• Example 1-3 preparation of a compound T3 according to the invention
• Example 1-4 preparation of a compound T4 according to the invention
• Example 1-5 preparation of a compound T5 according to the invention
• the reaction mixture is left under stirring for 60 minutes at 90°C ⁇ 1°C.
• the compound T5 obtained is formulated using a surfactant of the ethoxylated alcohol type (ethoxylated octanol with ten equivalents of ethylene oxide) in water with the addition of 1000 ppm of a biocidal agent (Biopol SMV Chemipol) and 1000 ppm of an antifoaming agent (Tego 1488 Evonik).
• a composition 5 is obtained consisting of 20% by mass of compound T5 according to the invention, 5% of surfactant and 75% by mass of water.
• Paint formulations F1 to F6 according to the invention are prepared respectively from aqueous compositions 1 to 6 of difunctional compounds T1 to T6 according to the invention. All the ingredients and proportions (% by mass) used are presented in Table 1.
• Example 3 characterization of paint formulations according to the invention
• the Brookfield viscosity measured at 25° C. and at 10 rpm and at 100 rpm (p Bki o and m Bkl oo in mPa.s) using a Brookfield DV-1 viscometer with RVT type spindles.
• the properties of the paint formulations are shown in Table 2.
• the difunctional compounds according to the invention are very effective in obtaining excellent viscosities at low and medium shear gradients for paint compositions.
• Example 4 characterization of paint formulations according to the invention
• the Plane Cone viscosity or ICI viscosity measured at a high shear rate (pi in mPa.s), was determined, 24 hours after their preparation and at room temperature, by means of a Cone & Plate Research Equipment London (REL) viscometer with a measurement scale of 0 to 5 poises, and the Stormer viscosity, measured at a medium shear rate (pS in Krebs Units or KU), using the standard module of a viscometer Brookfield KU-2.
• the properties of the paint formulations are shown in Table 3.
• the difunctional compounds according to the invention make it possible to prepare paint formulations whose viscosities are particularly well controlled.
• the viscosity pi is particularly high and the mi/ps ratio is then excellent.
• the compounds according to the invention allow an excellent compromise between the viscosity at high shear gradient and the viscosity at low shear gradient.
• Example 5 Characterization of a Paint Formulation According to the Invention Analogously to Example 4, the Stormer viscosity of formulation 6 comprising compound 6 according to the invention was determined.
• the Stormer viscosity of this formulation 6 is 122 KU.
• the difunctional compounds according to the invention therefore also make it possible to prepare paint formulations whose viscosity ps is particularly high.

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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)
• Materials Engineering (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Wood Science & Technology (AREA)
• General Chemical & Material Sciences (AREA)
• Dispersion Chemistry (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Polyurethanes Or Polyureas (AREA)

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• 2020
  • 2020-07-27 FR FR2007894A patent/FR3112785B1/fr active Active
• 2021
  • 2021-07-26 CN CN202180047009.6A patent/CN115916860A/zh active Pending
  • 2021-07-26 US US18/004,946 patent/US20230340280A1/en active Pending
  • 2021-07-26 EP EP21755001.1A patent/EP4188977A1/de active Pending
  • 2021-07-26 WO PCT/FR2021/000084 patent/WO2022023625A1/fr not_active Ceased

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