Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C265/00—Derivatives of isocyanic acid
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  • 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
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
  • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
  • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C263/00—Preparation of derivatives of isocyanic acid
  • C07C263/16—Preparation of derivatives of isocyanic acid by reactions not involving the formation of isocyanate groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
  • C07C269/02—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from isocyanates with formation of carbamate groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
  • C07C271/06—Esters of carbamic acids
  • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
  • C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
  • C07C271/06—Esters of carbamic acids
  • C07C271/32—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
  • C07C271/36—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
• • 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
  • C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
  • C08G18/2825—Alkanols, cycloalkanols or arylalkanols including terpenealcohols having at least 6 carbon atoms
• • C—CHEMISTRY; METALLURGY
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  • 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
  • C08G18/70—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
  • 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
  • C08G18/80—Masked polyisocyanates
  • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
  • C08G18/8064—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds
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  • 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
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  • 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
  • C09D105/00—Coating compositions based on polysaccharides or on their derivatives, not provided for in groups C09D101/00 or C09D103/00
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  • 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
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  • C09D17/00—Pigment pastes, e.g. for mixing in paints
  • C09D17/001—Pigment pastes, e.g. for mixing in paints in aqueous medium
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  • 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
  • C09D17/004—Pigment pastes, e.g. for mixing in paints containing an inorganic pigment
  • C09D17/007—Metal oxide
  • C09D17/008—Titanium dioxide
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  • 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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  • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
  • C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
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  • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
  • C09D7/40—Additives
  • C09D7/60—Additives non-macromolecular
  • C09D7/61—Additives non-macromolecular inorganic
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  • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
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  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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  • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
  • C07C2601/14—The ring being saturated

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. Indeed, during its preparation, its storage, its application or its drying, 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.
• the tool immersed and then removed from the paint pot carrying a large quantity of paint will avoid having to be reloaded more frequently. 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.
• Reduced viscosity at low to medium shear rates will also provide a good taut appearance after application of paint, especially paint monolayer, on a substrate whose coated surface will then present a very regular appearance, without bumps or hollows. 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.
• JPH06322392 describes detergent dissolution additives which are prepared from diols or polyethers.
• Document EP0295031 discloses a surfactant compound for a crosslinkable isocyanate resin prepared from polyethers.
• Document US4301083 relates to the preparation of polyether derivatives from halides.
• 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. a molar equivalent of at least one non-alkoxylated compound (a) chosen from:
• - branched aliphatic monoisocyanate compounds (a2) comprising from 6 to 40 non-alkoxylated carbon atoms
• - cycloaliphatic monoisocyanate (a3) compounds comprising from 6 to 40 non-alkoxylated carbon atoms
• alO polyaromatic monohaloalkylene
• polyaromatic monoalcohols (b5) comprising from 10 to 80 polyethoxylated carbon atoms comprising from 80 to 500 oxyethylene groups.
• the compounds (al) to (a5) result from the prior reaction of a diisocyanate compound and, respectively:
• cycloaliphatic monoalcohol comprising 6 to 40 non-alkoxylated carbon atoms
• polyaromatic monoalcohol comprising 10 to 80 non-alkoxylated carbon atoms.
• 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 diisocyanate compound is a compound in which the two isocyanate groups have different reactivities.
• the diisocyanate compound can be chosen from unsymmetrical diisocyanate compounds, preferably IPDI.
• the diisocyanate compound can also be 2,6 TDI.
• the diisocyanate compound can be chosen from:
• H12MDI methylene bis(4-cyclohexylisocyanate)
• HDI hexamethylene diisocyanate
• PDI pentamethylene diisocyanate
• the difunctional compound T is prepared from at least one compound (a1) to (a5) comprising an isocyanate group or from at least one compound (a6) to (a1O) comprising a halogen atom and a compound (b) capable of reacting with this isocyanate group or with this halogen atom 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 compounds (a1) to (a5) and of compound (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.
• the preferred metal derivative is selected from a Bi derivative, an Sn derivative and a Ti derivative.
• the condensation of the compounds (a6) to (alO) and of the compound (b) is carried out in the presence of a catalyst, in particular a base, for example a strong base, such as KOH, NaOH .
• a catalyst in particular a base, for example a strong base, such as KOH, NaOH .
• the reaction implements a single compound (a) or else the reaction implements two or three different compounds (a).
• the monohalogen compound is chosen from a chlorine compound, a bromine compound, an iodine compound and combinations thereof, preferably the monohalogen compound is a bromine compound.
• the monoaromatic monohaloalkylene compounds (a9) are compounds comprising a single monohalogenated aromatic group via an alkylene group.
• the halogen atom is not directly carried by the aromatic group.
• the polyaromatic monohaloalkylene (alO) compounds are compounds comprising at least two groups aromatics, at least one of which is monohalogenated via an alkylene group.
• the halogen atom is not directly carried by an aromatic group.
• compound (a) is such that:
• the hydrocarbon chain of compound (al) or of compound (a6) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 16 carbon atoms, more preferably compound (al) or the compound (a6) is chosen from non-alkoxylated n-octanyl, non-alkoxylated n-decanyl, non-alkoxylated n-dodecanyl, non-alkoxylated n-hexadecanyl, or
• the hydrocarbon chain of compound (a2) or of compound (a7) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 16 carbon atoms, more preferably compound (a2) or the compound (a7) is chosen from non-alkoxylated ethyl-hexanyl, non-alkoxylated iso-octanyl, non-alkoxylated iso-nonanyl, non-alkoxylated iso-decanyl, non-alkoxylated propyl-heptanyl, non-alkoxylated butyl-octanyl, non-alkoxylated iso-dodecanyl, non-alkoxylated iso-hexadecanyl, an alkyl group derived from a non-alkoxylated oxo alcohol, an alkyl group derived from a non-alkoxylated Guerbet alcohol, or
• the hydrocarbon chain of compound (a3) or of compound (a8) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 20 carbon atoms, more preferably compound (a3) or the compound (a8) is chosen from non-alkoxylated ethyl-cyclohexanyl, non-alkoxylated n-nonyl-cyclohexanyl, non-alkoxylated n-dodecyl-cyclohexanyl, or
• the hydrocarbon chain of compound (a4) or of compound (a9) comprises from 12 to 30 carbon atoms or from 12 to 22 carbon atoms, preferably compound (a4) or compound (a9) is chosen from n- non-alkoxylated pentadocecyl-phenyl or
• the hydrocarbon chain of the compound (a5) or of the compound (alO) comprises from 10 to 60 carbon atoms, preferably the compound (a5) or the compound (alO) is chosen from non-alkoxylated naphthyl, non-alkoxylated distyryl-phenyl alkoxylated, non-alkoxylated tristyryl-phenyl, non-alkoxylated pentastyryl-cumyl-phenyl.
• monoalcohols are compounds comprising a single hydroxyl group (OH) which is terminal.
• the polyethoxylated monoalcohols are compounds comprising a hydrocarbon chain which comprises several oxyethylene groups and a terminal hydroxyl (OH) group.
• the polyethoxylated monoalcohols are compounds of formula R-(LO) n -H in which R represents a hydrocarbon chain, n represents the number of polyethoxylations and L, identical or different, independently represents a linear alkylene group comprising 2 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 R'-OH in which R' 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 R or R′.
• the polyethoxylated monoalcohols (b1) and (b3) comprise from 105 to 400 ethoxylated groups or from 105 to 200 ethoxylated groups.
• the polyethoxylated monoalcohols (b2), (b4) and (b5) comprise from 80 to 400 ethoxylated groups or from 100 to 200 ethoxylated groups.
• the polyethoxylated compounds (b) used may comprise a number of identical or different ethoxylated groups.
• the ethoxylated groups are oxyethylene groups (-CH2CH2O-).
• compound T is a compound comprising ethoxylated groups.
• compound T has a degree of polyethoxylation of 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 compound (bl) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 16 carbon, more preferably the compound (bl) is chosen from polyethoxylated n-octanol, polyethoxylated n-decanol, polyethoxylated n-dodecanol, polyethoxylated n-hexadecanol, or - the hydrocarbon chain of the compound (b2) comprises from 6 to 30 atoms of carbon, preferably from 6 to 20 carbon atoms or from 8 to 16 carbon atoms, more preferably compound (b2) is chosen from polyethoxylated ethyl-hexanol, polyethoxylated iso-octanol, polyethoxylated iso-nonanol, polyethoxylated iso-decanol, polyethoxylated propy
• the hydrocarbon chain of compound (b3) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 20 carbon atoms, more preferably compound (b3) is chosen from ethyl-cyclohexanol polyethoxylated, polyethoxylated n-nonyl-cyclohexanol, polyethoxylated n-dodecyl-cyclohexanol, or
• the hydrocarbon chain of compound (b4) comprises from 12 to 30 carbon atoms or from 12 to 22 carbon atoms, preferably compound (b4) is chosen from polyethoxylated n-pentadocecyl-phenol or
• the hydrocarbon chain of compound (b5) comprises from 10 to 60 carbon atoms, preferably compound (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. a molar equivalent of at least one non-alkoxylated compound (a) chosen from:
• - monohalogenated cycloaliphatic compounds comprising from 6 to 40 non-alkoxylated carbon atoms
• - monoaromatic monohaloalkylene compounds comprising from 7 to 30 non-alkoxylated carbon atoms
• alO polyaromatic monohaloalkylene
• polyaromatic monoalcohols (b5) comprising from 10 to 80 polyethoxylated carbon atoms comprising from 80 to 500 oxyethylene groups.
• the condensation of the compounds (al) to (a5) 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 chosen 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 (a6) to (alO) and of the compound (b) is carried out in the presence of a catalyst, in particular a base, for example a strong base, such as KOH, NaOH .
• a catalyst in particular a base, for example a strong base, such as KOH, NaOH .
• the condensation of compounds (a) and (b) is carried out in an organic solvent.
• organic solvents are solvents non-reactive with the isocyanate functions or with the halogen atoms of compound (a), in particular the solvents chosen from hydrocarbon solvents (in particular Cs to C30 petroleum fractions), 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 an 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 surfactant compound, preferably a hydroxylated surfactant compound, for example alkyl-polyalkylene glycol, in particular alkyl-polyethylene glycol and alkyl-polypropylene glycol;
• 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, including 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 difunctional compounds according to the invention
• Example 1-1 preparation of a compound T1 according to the invention
• reaction mixture is left under stirring for 15 minutes. Then, it is verified that the theoretical rate of NCO functions is reached by a return 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 present in the medium. The 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. Then, the contents of container 2 are poured into container 1. Stirring is maintained for 60 minutes at 90 ⁇ 1°C. It is checked that the level of NCO function is zero indicating the end of the reaction.
• 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 1,000 ppm of a biocidal agent (Biopol SMV Chemipol) and 1,000 ppm of an anti-foaming agent (Tego 1488 Evonik).
• a composition 1 consisting of 20% by mass of compound T1 according to the invention and 80% by mass of water is obtained.
• Example 1-2 preparation of a compound T2 according to the invention
• 15.67 g of IPDI are introduced into a 100 mL three-necked glass flask (receptacle 2), to which 400 ppm of bismuth carboxylate catalyst are added.
• the medium is purged with nitrogen and then heated to 50°C. When this temperature is reached, 11.16 g of decanol are gradually introduced. After complete addition, the reaction mixture is left under stirring for 15 minutes. Then, it is verified that the theoretical rate of NCO functions is reached by a return dosing.
• the contents of container 2 are poured into container 1. Stirring is maintained for 60 minutes at 90 ⁇ 1°C. It is checked that the NCO function level is zero indicating the end of the reaction. If this is non-zero, the reaction is prolonged for periods of 15 minutes until the reaction is complete. When the rate reaches zero, the compound T2 obtained is formulated in water with the addition of 1,000 ppm of a biocidal agent (Biopol SMV Chemipol) and 1,000 ppm of an anti-foaming agent (Tego 1488 Evonik). A composition 2 is obtained consisting of 20% by mass of compound T2 according to the invention and 80% by mass of water.
• a biocidal agent Biopol SMV Chemipol
• an anti-foaming agent Tego 1488 Evonik
• Example 1-3 preparation of a compound T3 according to the invention
• Example 1-5 preparation of a compound T5 according to the invention
• Example 2 preparation of paint formulations according to the invention
• the paint formulations F1 to F5 according to the invention are prepared from aqueous compositions 1 to 5 respectively of difunctional compounds T1 to T5 according to the invention. All the ingredients and proportions (% by mass) used are presented in Table 1.
• 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 Cone Plane viscosity or ICI viscosity measured at high shear gradient, was determined 24 hours after their preparation and at room temperature. (pi in mPa.s), using 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 Brookfield KU-2 viscometer.
• the properties of the paint formulations are shown in Table 3. Table 3
• the difunctional compounds according to the invention make it possible to prepare paint formulations whose viscosities are particularly well controlled.
• the viscosity mi is particularly high and the ratio mi/ps 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.

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