RHEOLOGY-MODIFYING URETHANE COMPOUND

Description

[0001] The invention relates to a rheology modifying compound. The urethane-functional compound of the invention can be prepared according to a multi-step process which uses different isocyanate-functional compounds. For the preparation of the urethane compound according to the invention, a monoisocyanate compound, in particular a monoisocyanate compound resulting from the separate condensation of an asymmetric diisocyanate compound with a reactive compound, is reacted with an alkylene glycol compound in the presence of a polyisocyanate compound. The invention also provides coating compositions comprising mineral particles and a urethane compound according to the invention.

[0002] Generally speaking, for aqueous coating compositions, and in particular for aqueous paint or varnish compositions, it is necessary to control the viscosity for both low or medium shear rates and high shear rates. Indeed, during its preparation, storage, application or drying, a paint formulation is subject to numerous constraints requiring particularly complex rheological properties.

[0003] During paint storage, pigment particles tend to settle by gravity. Stabilizing the dispersion of these pigment particles then requires a paint formulation with high viscosity at very low shear rates corresponding to the limiting velocity of the particles.

[0004] Paint pick-up is the amount of paint picked up by an application tool, such as a paintbrush, brush, or roller. A tool dipped and then removed from the paint pot by picking up a large amount of paint will avoid the need for frequent re-dipping. 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. Therefore, the paint formulation should also have a high viscosity at low or medium shear rates.

[0005] In addition, a high filling power of the paint must be sought so that when it is applied to a substrate, a significant quantity of paint is deposited during each pass. A high filling power then makes it possible to obtain a larger wet film during each pass of the tool. A high viscosity of the paint formulation must therefore be sought at high shear rates.

[0006] High viscosity at high shear rates will also reduce or eliminate the risk of splatter or droplet formation during paint application.

[0007] A reduced viscosity at low or medium shear rates will also allow for a good taut appearance after application of the paint, particularly a single-coat paint, on a substrate whose coated surface will then have a very regular appearance, without bumps or hollows. The final visual appearance of the dry film is then much better.

[0008] Furthermore, after being deposited on a surface, especially a vertical surface, the paint should not form any drips. It is then necessary that the paint formulation has a high viscosity at low and medium shear rates.

[0009] Finally, after being deposited on a surface, the paint should have a significant leveling capacity. A reduced viscosity at low and medium shear rates of the paint formulation is then required.

[0010] Compounds of the HEUR type ( hydrophobically modified ethoxylated urethanesor ethoxylated and hydrophobically modified urethanes) are known as rheology modifying agents.

[0011] US 4,180,491 describes the preparation of various polyurethane compounds. In preparing these compounds, a first step consists of reacting a polyethylene glycol (PEG) with a monoisocyanate, until the isocyanate functions of the monoisocyanate are completely consumed. Then, in a second step, the PEG-monoisocyanate condensate, produced in the first step, is reacted with a triisocyanate compound.

[0012] Documents EP 2444432 and FR 2894980 describe urethane compounds and their use.

[0013] However, known HEUR-type compounds do not always provide a satisfactory solution. In particular, the rheology-modifying compounds of the state of the art do not allow for a satisfactory improvement in the compromise between Stormer viscosity (measured at low or medium shear rates and expressed in KU units) and ICI viscosity (measured at high or very high shear rates and expressed in s -1< ). In particular, known rheology-modifying compounds do not always allow for an increase in the ICI viscosity / Stormer viscosity ratio.

[0014] There is therefore a need for improved rheology modifying agents.

[0015] The urethane compound according to the invention makes it possible to provide a solution to all or part of the problems of rheology modifying agents of the state of the art.

[0016] Thus, the invention provides a urethane compound prepared in the absence of any diisocyanate compound, by reaction: (A) of at least one monoisocyanate compound chosen from: (A1) a compound comprising a single isocyanate function and (A2) at least one monoisocyanate compound resulting from the separate reaction (A2-1) of at least one compound comprising at least one labile hydrogen atom and (A2-2) of at least one dissymmetrical diisocyanate compound, (B) of at least one isocyanate compound comprising more than 2 isocyanate functions, and (C) of at least one compound of formula (I): (HO)-L n -(OH) (I) wherein L independently represents a poly(alkylene glycol) residue and n represents a number ranging from 40 to 400, the monoisocyanate compound being reacted with the alkylene glycol compound in the presence of the polyisocyanate compound.

[0017] Preferably according to the invention, the condensation of compounds (A), (B) and (C) is carried out in the presence of a catalyst. This catalyst may be chosen from acetic acid, 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 may also participate in the catalysis of the reaction. As examples of metal derivatives, a preferred derivative is selected from dibutyl bismuth dilaurate, dibutyl bismuth diacetate, dibutyl bismuth oxide, bismuth carboxylate, dibutyl tin dilaurate, dibutyl tin diacetate, dibutyl tin oxide, a mercury derivative, a lead derivative, zinc salts, manganese salts, a compound comprising chelated zirconium, a compound comprising chelated aluminum. The preferred metal derivative is selected from a Bi derivative and a Sn derivative.

[0018] Advantageously, the urethane compound according to the invention is a compound having a hydrophilic character. It can be formulated in an aqueous medium.

[0019] According to the invention, the monoisocyanate compounds (A1) and (A2) comprise only one isocyanate function. These are reagents known as such or prepared for the purposes of the invention. Thus, the compounds (A1) and (A2) comprise only one isocyanate function which is reactive during the reaction with the compounds (B) and (C). The reaction of these monoisocyanate compounds (A1) and (A2) with the compounds (B) and (C) is therefore carried out in the absence of a diisocyanate compound.

[0020] Preferably according to the invention, the monoisocyanate compound (A1) is a compound of formula (II): R-NCO (II) in which R represents a linear, branched or cyclic, saturated, unsaturated or aromatic hydrocarbon group, preferably a linear, branched or cyclic alkyl group comprising from 6 to 20 carbon atoms or a linear, branched or cyclic alkenyl group comprising from 6 to 20 carbon atoms.

[0021] Also preferably according to the invention, the monoisocyanate compound (A1) is a compound chosen from: les composés monoisocyanates aromatiques, notamment phenyl isocyanate, diphenylmethane monoisocyanate, 2-phenylethyl isocyanate, 4-tolyl isocyanate, 2-tolyl isocyanate, 2,5-dimethylphenyl isocyanate, 3,4-dimethylphenyl isocyanate, 2,3-dimethylphenyl isocyanate, 4-isocyanato-4'-methyldiphenylmethane ; les composés monoisocyanates aromatiques polyfonctionnels, notamment 2-methoxy-4-nitrophenyl isocyanate, polymethylene polyphenyl isocyanate ; les composés alkyl-monoisocyanates, notamment hexyl-isocyanate, heptyl-isocyanate, octyl-isocyanate, n-nonyl-isocyanate, decyl-isocyanate, undecyl-isocyanate, dodecyl-isocyanate, tridecyl-isocyanate, tetradecyl-isocyanate, cetyl-isocyanate, 2-ethyl-hexyl-isocyanate, n-octyl-isocyanate, isononyl-isocyanate, stearyl-isocyanate ; les composés cycloalkyl-monoisocyanates, notamment cyclohexyl-isocyanate, 1-isocyanatomethyl-1,3,3-trimethylcyclohexane.

[0022] Preferred monoisocyanate compounds (A1) are 2-ethyl-hexanol-isocyanate, hexyl-isocyanate, heptyl-isocyanate, octyl-isocyanate, n-nonyl-isocyanate, 2-ethyl-hexyl-isocyanate, n-octyl-isocyanate, isononyl-isocyanate.

[0023] According to the invention, the compound (A2) results from the prior and separate reaction of at least one compound (A2-1) and at least one compound (A2-2).

[0024] Advantageously according to the invention, the urethane compound according to the invention is prepared by using a molar quantity of compound (A2-1) which is greater than or equal to the molar quantity of compound (A2-2). Preferably, the molar quantity of functions comprising at least one labile hydrogen atom, in particular the molar quantity of hydroxyl groups, of the compound (A2-1) is greater than or equal to the molar quantity of isocyanate functions of the compound (A2-2).

[0025] Thus, the diisocyanate compound (A2-2) is completely transformed or completely consumed during the reaction to prepare the monoisocyanate compound (A2). It is not present and therefore does not intervene as such during the reaction which involves compounds (B) and (C).

[0026] Furthermore, and essentially according to the invention, the asymmetrical nature of the diisocyanate compound (A2-2) leads to a different reactivity of the two isocyanate functions that it comprises. Indeed, in general, the reaction kinetics of the two isocyanate functions are different. Thus, the urethane compound according to the invention is functionalized in a controlled manner.

[0027] As another monoisocyanate compound, the condensation reaction according to the invention can therefore also use a monoisocyanate compound (A2). According to the invention, the compound (A2) is prepared in a reaction separate from the condensation reaction according to the invention. The monoisocyanate compound (A2) is therefore produced by the reaction: (A2-1) of at least one compound comprising at least one labile hydrogen atom and (A2-2) of at least one asymmetric diisocyanate compound.

[0028] Preferably according to the invention, the reaction for preparing compound (A2) is a catalyzed reaction.

[0029] More preferably according to the invention, the reaction is catalyzed by means of acetic acid, an amine, preferably 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 may also participate in the catalysis of the reaction.

[0030] As examples of metal derivatives, a preferred derivative is selected from dibutyl bismuth dilaurate, dibutyl bismuth diacetate, dibutyl bismuth oxide, bismuth carboxylate, dibutyl tin dilaurate, dibutyl tin diacetate, dibutyl tin oxide, a mercury derivative, a lead derivative, zinc salts, manganese salts, a compound comprising chelated zirconium, a compound comprising chelated aluminum. The preferred metal derivative is selected from a Bi derivative and a Sn derivative.

[0031] According to the invention, the monoisocyanate compound (A2) is therefore prepared by prior condensation of at least one compound (A2-1) and at least one compound (A2-2). Once the condensation reaction has been carried out, the monoisocyanate compound (A2) has only one residual reactive isocyanate function.

[0032] The compound (A2-1) is preferably a compound comprising at least one labile hydrogen atom reactive with the asymmetric diisocyanate compound. More preferably, it is a compound (A2-1) comprising at least one hydroxyl group. In a particularly preferred manner, the compound (A2-1) is a monoalcohol, for example a linear, branched or cyclic C 5 -C 14 monoalcohol, in particular a linear or branched C 6 -C 14 monoalcohol, in particular a linear, branched or cyclic C 8 -C 12 monoalcohol.

[0033] As other compounds (A2-1) according to the invention, it is possible to use a compound comprising a primary amine function or a secondary amine function; a carboxylic acid; a mercaptan compound.

[0034] The compound (A2-2) is preferably a compound selected from unsymmetrical aromatic diisocyanate compounds and unsymmetrical alicyclic diisocyanate compounds. As preferred examples of compounds (A2-2), a compound selected from 2,4'-diphenylmethylene diisocyanate (2,4'-MDI), 2,4'-dibenzyl diisocyanate (2,4'-DBDI), 2,4-toluene diisocyanate (2,4-TDI) and isophorone diisocyanate (IPDI) may be used.

[0035] In addition to the monoisocyanate compound (A), the condensation reaction also involves a compound (B) which comprises more than 2 isocyanate functions. Preferably, the compound (B) is an isocyanate compound comprising 3, 4, 5 or 6 isocyanate functions. More preferably, it comprises 3 isocyanate functions.

[0036] According to the invention, compound (B) may also be chosen from isocyanate compounds comprising more than 2.5 isocyanate functions, preferably more than 2.6 isocyanate functions, more preferably more than 2.7 isocyanate functions, even more preferably 3 or more than 3 isocyanate functions.

[0037] As examples of preferred compounds (B) according to the invention, the following are used: triphenylmethane-4,4',4"-triisocyanate or 1,1',1"-methylidynetris (4-isocyanatobenzene); or an isocyanurate compound, in particular an isocyanurate compound of a compound chosen from: ∘ symmetrical aromatic diisocyanate compounds, preferably: ▪ 2,2'-diphenylmethylene diisocyanate (2,2'-MDI) and 4,4'-diphenylmethylene diisocyanate (4,4'-MDI); ▪ 4,4'-dibenzyl diisocyanate (4,4'-DBDI); ▪ 2,6-toluene diisocyanate (2,6-TDI); ▪ m-xylylene diisocyanate (m-XDI); ∘ symmetrical alicyclic diisocyanate compounds, preferably methylene bis(4-cyclohexylisocyanate) (H 12 MDI); ∘ symmetrical aliphatic diisocyanate compounds, preferably hexamethylene diisocyanate (HDI), pentamethylene diisocyanate (PDI); ∘ unsymmetrical aromatic diisocyanate compounds, preferably: ▪ 2,4'-diphenylmethylene diisocyanate (2,4'-MDI); ▪ 2,4'-dibenzyl diisocyanate (2,4'-DBDI); ▪ 2,4-toluene diisocyanate (2,4-TDI);a trimeric biurea compound, in particular a trimeric biurea compound of a compound chosen from: ∘ symmetrical aromatic diisocyanate compounds, preferably: ▪ 2,2'-diphenylmethylene diisocyanate (2,2'-MDI) and 4,4'-diphenylmethylene diisocyanate (4,4'-MDI); ▪ 4,4'-dibenzyl diisocyanate (4,4'-DBDI); ▪ 2,6-toluene diisocyanate (2,6-TDI); ▪ m-xylylene diisocyanate (m-XDI); ∘ symmetrical alicyclic diisocyanate compounds, preferably methylene bis(4-cyclohexylisocyanate) (H 12 MDI); ∘ symmetrical aliphatic diisocyanate compounds, preferably hexamethylene diisocyanate (HDI), pentamethylene diisocyanate (PDI); o unsymmetrical aromatic diisocyanate compounds, preferably: ▪ 2,4'-diphenylmethylene diisocyanate (2,4'-MDI); ▪ 2,4'-dibenzyl diisocyanate (2,4'-DBDI); ▪ 2,4-toluene diisocyanate (2,4-TDI); unsymmetrical alicyclic diisocyanate compounds, preferably isophorone diisocyanate (IPDI). ;

[0038] According to the invention, compound (B) is preferentially chosen from triphenylmethane-4,4',4"-triisocyanate, 1,1',1"-methylidynetris (4-isocyanatobenzene), an HDI isocyanurate, an IPDI isocyanurate, a PDI isocyanurate, an HDI biurea trimer and an IPDI biurea trimer, a PDI biurea trimer.

[0039] In addition to compounds (A) and (B), the condensation reaction also involves a compound (C) of formula (I).

[0040] Preferably, compound (C) is a compound of formula (I) in which: L independently represents a poly(ethylene glycol) residue; or n represents a number from 50 to 400; or L independently represents a poly(ethylene glycol) residue and n represents a number from 50 to 400.

[0041] More preferably, compound (C) is a compound of formula (I) in which: L independently represents a poly(ethylene glycol) residue; or n represents a number from 100 to 300; or L independently represents a poly(ethylene glycol) residue and n represents a number from 100 to 300.

[0042] Also preferably, compound (C) is a compound whose molar mass (MW) ranges from 1,500 to 20,000 g / mol, preferably from 2,000 to 20,000 g / mol, more preferably from 4,000 to 15,000 g / mol. According to the invention, the molar mass is calculated from the hydroxyl number determined according to DIN 53240-1, now DIN EN ISO 4629-1, by applying the formula: (56,100 x functionality in OH groups) / hydroxyl number.

[0043] During the condensation reaction for preparing the urethane compound according to the invention, the amounts of compounds (A), (B) and (C) can vary. Preferably, the molar amount of compound (C) is approximately two times less than the molar amount of monoisocyanate compound (A).

[0044] In addition to a urethane compound, the invention also relates to a process for preparing this compound. Thus, the invention provides a process for preparing a urethane compound in the absence of any diisocyanate compound, by reacting: (A) of at least one monoisocyanate compound chosen from: (A1) a compound comprising a single isocyanate function and (A2) at least one monoisocyanate compound resulting from the separate reaction (A2-1) of at least one compound comprising at least one labile hydrogen atom and (A2-2) of at least one asymmetric diisocyanate compound, (B) of at least one isocyanate compound comprising more than 2 isocyanate functions, and (C) of at least one compound of formula (I): (HO)-L n -(OH) (I) in which L independently represents a poly(alkylene glycol) residue and n represents a number ranging from 40 to 400, the monoisocyanate compound being reacted with the alkylene glycol compound in the presence of the polyisocyanate compound.

[0045] Preferably according to the invention for the process according to the invention, the condensation of compounds (A), (B) and (C) is carried out in the presence of a catalyst. This catalyst may be chosen from acetic acid, 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, preferably chosen from dibutyl bismuth dilaurate, dibutyl bismuth diacetate, dibutyl bismuth oxide, bismuth carboxylate, dibutyl tin dilaurate, dibutyl tin diacetate, dibutyl tin oxide, a mercury derivative, a lead derivative, zinc salts, manganese salts, a compound comprising chelated zirconium, a compound comprising chelated aluminum. The preferred metal derivative is selected from a Bi derivative and a Sn derivative.

[0046] For the process according to the invention, the monoisocyanate compounds (A1) and (A2) comprise only one isocyanate function. The reaction of these compounds with the compounds (B) and (C) is therefore carried out in the absence of a diisocyanate compound.

[0047] Preferably for the process according to the invention, the monoisocyanate compound (A1) is a compound of formula (II): R-NCO (II) in which R represents a linear, branched or cyclic, saturated, unsaturated or aromatic hydrocarbon group, preferably a linear, branched or cyclic alkyl group comprising from 6 to 20 carbon atoms or a linear, branched or cyclic alkenyl group comprising from 6 to 20 carbon atoms.

[0048] Also preferably for the process according to the invention, the monoisocyanate compound (A1) is a compound chosen from: les composés monoisocyanates aromatiques, notamment phenyl isocyanate, diphenylmethane monoisocyanate, 2-phenylethyl isocyanate, 4-tolyl isocyanate, 2-tolyl isocyanate, 2,5-dimethylphenyl isocyanate, 3,4-dimethylphenyl isocyanate, 2,3-dimethylphenyl isocyanate, 4-isocyanato-4'-methyldiphenylmethane ; les composés monoisocyanates aromatiques polyfonctionnels, notamment 2-methoxy-4-nitrophenyl isocyanate, polymethylene polyphenyl isocyanate, les composés alkyl-monoisocyanates, notamment hexyl-isocyanate, heptyl-isocyanate, octyl-isocyanate, n-nonyl-isocyanate, decyl-isocyanate, undecyl-isocyanate, dodecyl-isocyanate, tridecyl-isocyanate, tetradecyl-isocyanate, cetyl-isocyanate, 2-ethyl-hexyl-isocyanate, n-octyl-isocyanate, isononyl-isocyanate, stearyl-isocyanate ; les composés cycloalkyl-monoisocyanates, notamment cyclohexyl-isocyanate, 1-isocyanatomethyl-1,3,3-trimethylcyclohexane.

[0049] Preferred compounds (A1) are 2-ethyl-hexanol-isocyanate, hexyl-isocyanate, heptyl-isocyanate, octyl-isocyanate, n-nonyl-isocyanate, 2-ethyl-hexyl-isocyanate, n-octyl-isocyanate, isononyl-isocyanate.

[0050] For the process according to the invention, the monoisocyanate compound (A2) is therefore prepared by separate and prior condensation of at least one compound (A2-1) and at least one compound (A2-2).

[0051] Advantageously for the process according to the invention, the compound (A2-1) is used in a molar quantity which is greater than or equal to the molar quantity of compound (A2-2). Preferably for the process according to the invention, the molar quantity of functions comprising at least one labile hydrogen atom, in particular the molar quantity of hydroxyl groups, of the compound (A2-1) is greater than or equal to the molar quantity of isocyanate functions of the compound (A2-2). Thus, the diisocyanate compound (A2-2) is completely transformed during the reaction for preparing the compound (A2). It is not present as a diisocyanate compound because one of its isocyanate functions has reacted with the compound (A2-1). It therefore does not intervene during the reaction which uses the compounds (B) and (C).

[0052] Furthermore, and in an essential manner for the process according to the invention, the asymmetrical nature of the diisocyanate compound (A2-2) leads to a different reactivity of the two isocyanate functions that it comprises. Indeed, in general, the reaction kinetics of the two isocyanate functions are different. Thus, the process according to the invention makes it possible to control the functionality of the urethane compound prepared.

[0053] As another monoisocyanate compound, the process according to the invention can also use a monoisocyanate compound (A2). For the process according to the invention, the compound (A2) is prepared in a reaction separate from the condensation reaction according to the invention. The monoisocyanate compound (A2) is therefore produced by the reaction: (A2-1) of at least one compound comprising at least one labile hydrogen atom and (A2-2) of at least one asymmetric diisocyanate compound.

[0054] Preferably for the process according to the invention, the reaction for preparing the monoisocyanate compound (A2) is a catalyzed reaction.

[0055] More preferably for the process according to the invention, the reaction is catalyzed by means of acetic acid, 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 may also participate in the catalysis of the reaction.

[0056] As examples of metal derivatives, a preferred derivative is selected from dibutyl bismuth dilaurate, dibutyl bismuth diacetate, dibutyl bismuth oxide, bismuth carboxylate, dibutyl tin dilaurate, dibutyl tin diacetate, dibutyl tin oxide, a mercury derivative, a lead derivative, zinc salts, manganese salts, a compound comprising chelated zirconium, a compound comprising chelated aluminum. The preferred metal derivative is selected from a Bi derivative and a Sn derivative.

[0057] For the process according to the invention, the monoisocyanate compound (A2) is therefore prepared by prior condensation of at least one compound (A2-1) and at least one compound (A2-2).

[0058] The compound (A2-1) is preferably a compound comprising at least one labile hydrogen atom reactive with the asymmetric diisocyanate compound. More preferably, it is a compound (A2-1) comprising at least one hydroxyl group. In a particularly preferred manner, the compound (A2-1) is a monoalcohol, for example a linear, branched or cyclic C 5 -C 14 monoalcohol, in particular a linear, branched or cyclic C 6 -C 14 monoalcohol, in particular a linear, branched or cyclic C 8 -C 12 monoalcohol. As other compounds (A2-1) according to the invention, it is possible to use a compound comprising a primary amine function or a secondary amine function; a carboxylic acid; a mercaptan compound.

[0059] The compound (A2-2) is preferably a compound selected from unsymmetrical aromatic diisocyanate compounds and unsymmetrical alicyclic diisocyanate compounds. As preferred examples of compounds (A2-2), a compound selected from 2,4'-diphenylmethylene diisocyanate (2,4'-MDI), 2,4'-dibenzyl diisocyanate (2,4'-DBDI), 2,4-toluene diisocyanate (2,4-TDI) and isophorone diisocyanate (IPDI) may be used.

[0060] In addition to the monoisocyanate compound (A), the process according to the invention also uses a compound (B) which comprises more than 2 isocyanate functions. Preferably for the process according to the invention, the compound (B) is an isocyanate compound comprising 3, 4, 5 or 6 isocyanate functions. More preferably, it comprises 3 isocyanate functions.

[0061] For the process according to the invention, the compound (B) may also be chosen from isocyanate compounds comprising more than 2.5 isocyanate functions, preferably more than 2.6 isocyanate functions, more preferably more than 2.7 isocyanate functions, even more preferably 3 or more than 3 isocyanate functions. As examples of preferred compounds (B) according to the process of the invention, the following are used: triphenylmethane-4,4',4"-triisocyanate or 1,1',1"-methylidynetris (4-isocyanatobenzene); or an isocyanurate compound, in particular an isocyanurate compound of a compound chosen from: ∘symmetrical aromatic diisocyanate compounds, preferably: ▪ 2,2'-diphenylmethylene diisocyanate (2,2'-MDI) and 4,4'-diphenylmethylene diisocyanate (4,4'-MDI); ▪ 4,4'-dibenzyl diisocyanate (4,4'-DBDI); ▪ 2,6-toluene diisocyanate (2,6-TDI); ▪ m-xylylene diisocyanate (m-XDI); ∘ symmetrical alicyclic diisocyanate compounds, preferably methylene bis(4-cyclohexylisocyanate) (H 12 MDI); ∘ symmetrical aliphatic diisocyanate compounds, preferably hexamethylene diisocyanate (HDI); o unsymmetrical aromatic diisocyanate compounds, preferably: ▪ 2,4'-diphenylmethylene diisocyanate (2,4'-MDI); ▪ 2,4'-dibenzyl diisocyanate (2,4'-DBDI); ▪ 2,4-toluene diisocyanate (2,4-TDI);a trimeric biurea compound, in particular a trimeric biurea compound of a compound chosen from: ∘ symmetrical aromatic diisocyanate compounds, preferably: ▪ 2,2'-diphenylmethylene diisocyanate (2,2'-MDI) and 4,4'-diphenylmethylene diisocyanate (4,4'-MDI); ▪ 4,4'-dibenzyl diisocyanate (4,4'-DBDI); ▪ 2,6-toluene diisocyanate (2,6-TDI); ▪ m-xylylene diisocyanate (m-XDI); ∘ symmetrical alicyclic diisocyanate compounds, preferably methylene bis(4-cyclohexylisocyanate) (H 12 MDI); ∘ symmetrical aliphatic diisocyanate compounds, preferably hexamethylene diisocyanate (HDI); ∘ unsymmetrical aromatic diisocyanate compounds, preferably: ▪ 2,4'-diphenylmethylene diisocyanate (2,4'-MDI); ▪ 2,4'-dibenzyl diisocyanate (2,4'-DBDI); ▪ 2,4-toluene diisocyanate (2,4-TDI); unsymmetrical alicyclic diisocyanate compounds, preferably isophorone diisocyanate (IPDI). ;

[0062] For the process according to the invention, the compound (B) is preferentially chosen from triphenylmethane-4,4',4"-triisocyanate, 1,1',1"-methylidynetris (4-isocyanatobenzene), an HDI isocyanurate, an IPDI isocyanurate, an HDI biurea trimer and an IPDI biurea trimer.

[0063] In addition to compounds (A) and (B), the method according to the invention also uses a compound (C) of formula (I). Preferably, compound (C) is a compound of formula (I) in which: L independently represents a poly(ethylene glycol) residue; or n represents a number from 50 to 400; or L independently represents a poly(ethylene glycol) residue and n represents a number from 50 to 400.

[0064] More preferably, compound (C) is a compound of formula (I) in which: L independently represents a poly(ethylene glycol) residue; or n represents a number from 100 to 300; or L independently represents a poly(ethylene glycol) residue and n represents a number from 100 to 300.

[0065] Also preferably for the process according to the invention, the compound (C) is a compound whose molar mass (MW) ranges from 1,500 to 20,000 g / mol, preferably from 2,000 to 20,000 g / mol, more preferably from 4,000 to 15,000 g / mol.

[0066] During the condensation reaction for preparing the urethane compound according to the invention, the amounts of compounds (A), (B) and (C) can vary. Preferably, the molar amount of compound (C) is approximately two times less than the molar amount of monoisocyanate compound (A).

[0067] In addition to a urethane compound and a method, the invention also relates to an aqueous composition comprising at least one urethane compound according to the invention.

[0068] The invention also relates to an aqueous composition comprising at least one urethane compound prepared according to the process of the invention.

[0069] The aqueous composition according to the invention may also comprise at least one additive, in particular an additive chosen from: an 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; solvents, in particular coalescing solvents, and hydrotropic compounds, for example glycol, butyl glycol, butyldiglycol, monopropylene glycol, ethylene glycol, ethylenediglycol, Dowanol products (CAS number 34590-94-8), Texanol products (CAS number 25265-77-4); antifoaming agents, biocidal agents.

[0070] The invention also provides an aqueous formulation that 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 mineral pigment or organic, organometallic or mineral particles, for example calcium carbonate, talc, kaolin, mica, silicates, silica, metal oxides, in particular titanium dioxide, iron oxides.

[0071] The aqueous formulation according to the invention may also comprise at least one agent chosen from a particle spacer agent, a dispersing agent, a steric stabilizing agent, an electrostatic stabilizing agent, an opacifying agent, a solvent, a coalescing agent, an antifoaming agent, a preservative, a biocidal agent, a spreading agent, a thickening agent, a film-forming copolymer and mixtures thereof.

[0072] Depending on the particular urethane compound or the additives it comprises, the formulation according to the invention can be implemented in many technical fields. Thus, the formulation according to the invention can be a coating formulation. Preferably, 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. Preferably, the formulation according to the invention is a paint formulation.

[0073] The invention also provides a concentrated aqueous pigment paste comprising at least one urethane compound according to the invention and at least one organic or mineral colored pigment.

[0074] The urethane compound according to the invention has properties allowing it to be used to modify or control the rheology of the medium comprising it. Thus, the invention also provides a method for controlling the viscosity of an aqueous composition.

[0075] This viscosity control method according to the invention comprises the addition of at least one urethane compound according to the invention to an aqueous composition. This viscosity control method may also comprise the addition of at least one urethane compound prepared according to the method of the invention.

[0076] Preferably, the viscosity control method according to the invention is implemented using an aqueous composition according to the invention.

[0077] Also preferably, the viscosity control method according to the invention is implemented by means of an aqueous formulation according to the invention.

[0078] The following examples illustrate the various aspects of the invention. Example 1: Preparation of urethane compounds according to the invention:

[0079] In a 3 L glass reactor (container 1) equipped with mechanical stirring, a vacuum pump, a nitrogen inlet and heated by means of a double jacket in which oil circulates, 594.4 g of compound (C) (polyethylene glycol of molecular mass (M w ) 10,000 or PEG 10,000) are introduced. This stirred medium is heated to 105°C and placed under an inert atmosphere.

[0080] At the same time, 39.59 g of compound (A2-2) (IPDI) are introduced into a 100 mL three-necked glass flask (container 2), to which 1.19 g of a bismuth catalyst (bismuth carboxylate) are added. The medium is purged with nitrogen and then heated to 50°C. When this temperature is reached, 23.18 g of compound (A2-1) (octan-1-ol) are gradually introduced using a syringe.

[0081] After complete addition, the reaction mixture is left stirring for 15 minutes. Then, it is checked that the theoretical level of NCO functions is reached by a back titration. 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 titrated with hydrochloric acid (1 N for example). The quantity of isocyanate functions present in the reaction medium can then be deduced.

[0082] 3.25 g of compound (B) (HDI isocyanurate) are then added and the mixture is stirred for 5 minutes.

[0083] Then, the contents of container 2, comprising the mixture of monoisocyanate and triisocyanate compounds, are poured into container 1. Stirring is continued for 60 minutes at 100 ± 2°C. Then, it is checked that the NCO function level is zero, indicating the end of the reaction. It is allowed to cool; the urethane compound 1 according to the invention is obtained.

[0084] In a similar manner, urethane compounds 2 to 10 are prepared according to the invention. Also in a similar manner, a comparative compound C1 is prepared by omitting the addition of compound (B).

[0085] All reagents and proportions (% by mass) used are presented in Table 1. Table 1 urethane compound 1 2 3 4 5 6 7 8 9 10 C1 (A2-1) octan-1-ol 3,50 3,51 3,51 3,52 1,75 4,29 3,09 (A2-1) octan-2-ol 3,51 (A2-1) Nopol * 4,44 (A2-1) 2-ethyl-hexanol 1,75 3,51 (A2-1) isononanol 3,87 (A2-2) IPDI 5,98 5,94 6,00 5,99 5,99 5,96 6,00 5,99 7,31 5,99 5,28 (B) HDI isocyanurate 0,49 0,32 0,49 0,49 0,60 (B) HDI biuret 0,34 0,50 0,50 0,50 (B) PDI isocyanurate 0,28 (C) PEG 10,000 89,85 89,12 90,09 89,94 89,94 89,5 90,14 89,96 89,94 91,47 (C) PEG 8000 87,74 bismuth catalyst 0,18 0,18 0,06 0,06 0,06 0,18 0,06 0,06 0,06 0,06 0,16 * 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-ethanol Example 2: preparation and characterization of aqueous compositions of urethane compounds according to the invention and of aqueous compositions comparative:

[0086] In the aqueous solution of urethane compound 1 according to the invention prepared according to Example 1, a polyethoxylated fatty alcohol (Mergital D8 Cognis product) is added as a surfactant. Then, water is added. An aqueous composition is obtained comprising approximately 20% by mass of hydrophobic urethane rheology modifier agent according to the invention, approximately 5% by mass of surfactant and approximately 75% of water. Approximately 1,000 ppm of a biocidal agent (Biopol SMV Chemipol product) and approximately 1,000 ppm of an antifoam agent (Tego 1488 Evonik product) are then added in order to obtain the aqueous composition 1 according to the invention.

[0087] In a similar manner, aqueous compositions 2 to 10 according to the invention are prepared from urethane compounds 2 to 10 according to the invention. Also in a similar manner, a comparative aqueous composition comprising comparative compound C1 of Example 1 is prepared.

[0088] All reagents and proportions (% by mass) used are presented in Table 2. Table 2 urethane compound 1 2 3 4 5 6 7 8 9 10 C1 (A2-1) octan-1-ol 0,71 0,72 0,72 0,72 0,36 0,87 0,62 (A2-1) octan-2-ol 0,72 (A2-1) Nopol *< 0,91 (A2-1) 2-ethyl-hexanol 0,36 0,72 (A2-1) isononanol 0,79 ethoxylated alcohol surfactant 5,10 5,10 5,10 5,10 5,10 5,10 5,10 5,10 5,10 5,12 5,08 (A2-2) IPDI 1,22 1,21 1,22 1,22 1,22 1,22 1,22 1,22 1,49 1,22 1,07 (B) HDI isocyanurate 0,10 0,07 0,10 0,10 0,12 (B) HDI biuret 0,07 0,10 0,10 0,10 (B) PDI isocyanurate 0,06 (C) PEG 10,000 18,33 18,18 18,38 18,35 18,35 18,26 18,39 18,35 18,35 18,69 (C) PEG 8000 17,90 bismuth catalyst 0,04 0,04 0,01 0,01 0,01 0,04 0,01 0,01 0,01 0,01 0,04 water 74,50 74,50 74,50 74,50 74,53 74,50 74,51 74,50 74,50 74,48 74,50 * 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-ethanol Example 3: Preparation and characterization of paint formulations according to the invention and of paint formulations comparative:

[0089] A paint formulation 1 according to the invention is prepared from the aqueous composition 1 according to the invention. All the ingredients and proportions (% by mass) used are presented in Table 3.

[0090] Paint formulations 2 to 10 according to the invention are prepared in a similar manner by replacing the aqueous urethane compound composition of Example 1 with aqueous compositions 2 to 10.

[0091] Also in a similar manner, comparative paint formulations are prepared from aqueous compositions of known rheology modifying compounds. Table 3 Ingredients : quantity (g): water 99,45 dispersing agent (Coadis BR3 Coatex) 3,9 biocidal agent (Acticide MBS Thor) 1,3 anti-foam agent (Airex 901W Evonik) 1,31 NH 4 OH (28%) 0,5 TiO 2 pigment (RHD2 Huntsman) 122,2 pigment CaCO 3 (Omyacoat 850 OG Omya) 84,5 binding agent (Acronal 290D Basf) 270,6 monopropylene glycol 6,5 solvent (Texanol Eastman) 6,5 anti-foam agent (Tego 825 Evonik) 0,65 aqueous composition 1 according to the invention 28,6 water supplement qsp 650 g in total

[0092] For each of the paint formulations, the following were determined 24 hours after preparation and at room temperature: Brookfield viscosity, measured at 25°C and at 10 rpm and 100 rpm, µ Bk10 and µ Bk100 (in mPa.s); Cone Plan viscosity or ICI viscosity, measured at high speed gradient, µ I (in mPa.s); Stormer viscosity, measured at medium speed gradient, µ S (in Krebs Units or KU, using the standard module).

[0093] The properties of the paint formulations are shown in Table 4. Table 4 formulation µ Bk10 µ Bk10 µ I µ S µ I / µ S comparative 2 960 1 900 250 100 2,5 1 according to the invention 2 800 1 587 300 95 3,2 2 according to the invention 3 060 1 818 310 100 3,1 3 according to the invention 2 960 1 723 315 98 3,2 4 according to the invention 3 080 1 793 305 99 3,1 5 according to the invention 4 380 2 316 315 103 3,1 6 according to the invention 2 570 1 472 285 94 3 7 according to the invention 2 785 1 648 300 97 3,1 8 according to the invention 2 850 1 685 300 97 3,1 9 according to the invention 3 000 1 723 290 98 3 10 according to the invention 2 460 1 427 270 92 2,9 Example 4: Preparation and characterization of aqueous compositions of urethane compounds according to the invention comprising a latex and comparative aqueous compositions comprising a latex :

[0094] The aqueous latex compositions are prepared by mixing, using a stirrer equipped with a turbine, 366.3 g of an acrylic binder (Encor 662 ACR Arkema Coating Resins) and alternatively: 169.95 g of water and 13.75 g of an aqueous composition comprising the urethane compound 1 according to the invention for the test incorporating 0.5% of the aqueous composition; 159.64 g of water and 24.06 g of an aqueous composition comprising the urethane compound 1 according to the invention for the test incorporating 0.875% of the aqueous composition; 149.32 g of water and 34.38 g of an aqueous composition comprising the urethane compound 1 according to the invention for the test incorporating 1.25% of the aqueous composition; 139.01 g of water and 44.69 g of an aqueous composition comprising the urethane compound 1 according to the invention for the test incorporating 1.625% of the aqueous composition; 128.7 g of water and 55 g of an aqueous composition comprising the urethane compound 1 according to the invention for the test incorporating 2% of the aqueous composition.

[0095] Similarly, an aqueous composition of urethane compound 2 according to the invention is prepared, also comprising a latex, and a comparative aqueous composition comprising a known rheology modifying compound and a latex.

[0096] For each of the compositions, the following were determined 24 hours after their preparation and at room temperature: Cone Plan viscosity or ICI viscosity, measured at high velocity gradient, µ I (in mPa.s); Stormer viscosity, measured at medium velocity gradient, µ S (in Krebs Units or KU, using the standard module).

[0097] The quantities of rheology modifying compounds used and the viscosity measurements of these compositions are presented in Table 5. Table 5 paint formulation µ I µ S µ I / µ S comparative (Coapur 3020 Coatex product) at 0.5% by weight of compound 5 66 0,08 at 0.875% by weight of compound 48 81 0,59 at 1.25% by weight of compound 91 87 1,05 at 1.625% by weight of compound 155 93 1,67 at 2% by weight of compound 244 100 2,44 urethane compound 1 at 0.5% by weight of urethane compound 1 20 59 0,34 at 0.875% by weight of urethane compound 1 66 68 0,97 at 1.25% by weight of urethane compound 1 135 77 1,75 at 1.625% by weight of urethane compound 1 218 87 2,51 at 2% by weight of urethane compound 1 323 95 3,40 urethane compound 2 at 0.5% by weight of urethane compound 2 20 65 0,31 at 0.875% by weight of urethane compound 2 62 74 0,84 at 1.25% by weight of urethane compound 2 116 80 1,45 at 1.625% by weight of urethane compound 2 191 88 2,17 at 2% by weight of urethane compound 2 274 94 2,91

[0098] Compared to the comparative urethane compound, the urethane compounds according to the invention make it possible to prepare aqueous latex compositions as well as paint compositions whose viscosities are particularly well controlled. In particular, the viscosity µ I is increased; the ratio µ I / µ S is then systematically higher when using the urethane compounds according to the invention.

Claims

1. A urethane compound prepared in the absence of any diisocyanate compound, by reaction: (A) of at least one monoisocyanate compound chosen among: (A1) a compound comprising a single isocyanate function and (A2) at least one monoisocyanate compound resulting from the separate reaction (A2-1) of at least one compound comprising at least one labile hydrogen atom and (A2-2) of at least one dissymmetric diisocyanate compound, (B) of at least one isocyanate compound comprising more than 2 isocyanate functions, and (C) of at least one compound of formula (I):         (HO)-Ln-(OH)     (I) in which L independently represents an alkylene glycol residue and n represents a number ranging from 40 to 400, the monoisocyanate compound being reacted with the alkylene glycol compound in the presence of the polyisocyanate compound.

2. The urethane compound according to claim 1, for which the monoisocyanate compound (A1) is: • a compound of formula (II):         R-NCO     (II) in which R represents a linear, branched or cyclic, saturated, unsaturated or aromatic hydrocarbon group, preferably a linear, branched or cyclic alkyl group comprising from 6 to 20 carbon atoms or a linear, branched or cyclic alkenyl group comprising from 6 to 20 carbon atoms; or is • a compound chosen among: ∘ aromatic monoisocyanate compounds, in particular phenyl isocyanate, diphenylmethane monoisocyanate, 2-phenylethyl isocyanate, 4-tolyl isocyanate, 2-tolyl isocyanate, 2,5-dimethylphenyl isocyanate, 3,4-dimethylphenyl isocyanate, 2,3-dimethylphenyl isocyanate, 4-isocyanato-4'-methyldiphenylmethane; ∘ polyfunctional aromatic monoisocyanate compounds, in particular 2-methoxy-4-nitrophenyl isocyanate, polymethylene polyphenyl isocyanate; ∘ alkyl monoisocyanate compounds, in particular hexyl isocyanate, heptyl isocyanate, octyl isocyanate, n-nonyl isocyanate, decyl isocyanate, undecyl isocyanate, dodecyl isocyanate, tridecyl isocyanate, tetradecyl isocyanate, cetyl isocyanate, 2-ethylhexyl isocyanate, n-octyl isocyanate, isononyl isocyanate, stearyl isocyanate; ∘ cycloalkyl monoisocyanate compounds, in particular cyclohexyl isocyanate, 1-isocyanatomethyl-1,3,3-trimethylcyclohexane.

3. The urethane compound according to one of claims 1 and 2, for which the reaction for preparing the monoisocyanate compound (A2) is a catalysed reaction, preferably catalysed by means of acetic acid, of an amine, preferably 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), or of at least one derivative of a metal chosen among Al, Bi, Sn, Hg, Pb, Mn, Zn, Zr, Ti, for example dibutylbismuth dilaurate, dibutylbismuth diacetate, dibutylbismuth oxide, bismuth carboxylate, dibutyltin dilaurate, dibutyltin diacetate, dibutyltin oxide, a mercury derivative, a lead derivative, zinc salts, manganese salts, a compound comprising zirconium chelate, a compound comprising aluminium chelate.

4. The urethane compound according to one of claims 1 to 3 - for which the compound (A2-1) is chosen among a compound comprising at least one labile hydrogen atom that is reactive with the disymmetric diisocyanate compound; a compound comprising at least one hydroxyl group; a compound comprising a primary amine function or a secondary amine function; a carboxylic acid; a mercaptan compound; preferably a compound comprising a hydroxyl group, in particular a monoalcohol, for example a C5-C14 linear, branched or cyclic monoalcohol, in particular a C6-C14 linear, branched or cyclic monoalcohol, especially a C8-C12 linear, branched or cyclic monoalcohol; or - for which the compound (A2-2) is chosen among: • dissymmetric aromatic diisocyanate compounds, preferably 2,4'-methylenediphenyl diisocyanate (2,4'-MDI), 2,4'-dibenzyl diisocyanate (2,4'-DBDI), 2,4-toluene diisocyanate (2,4-TDI); • dissymmetric alicyclic diisocyanate compounds, preferably isophorone diisocyanate (IPDI).

5. The urethane compound according to one of claims 1 to 4, for which: • the compound (B) is an isocyanate compound comprising 3, 4, 5 or 6 isocyanate functions; or for which • the compound (B) is an isocyanate compound comprising more than 2.5 isocyanate functions, preferably more than 2.6 isocyanate functions, more preferentially more than 2.7 isocyanate functions, even more preferentially 3 or more than 3 isocyanate functions; or for which • the compound (B) is triphenylmethane-4,4',4"-triisocyanate or 1,1', 1"-methylidynetris(4-isocyanatobenzene); or for which • the compound (B) is an isocyanurate compound, in particular an isocyanurate compound of a compound chosen among: ∘ symmetric aromatic diisocyanate compounds, preferably: ▪ 2,2'-methylenediphenyl diisocyanate (2,2'-MDI) and 4,4'-methylenediphenyl diisocyanate (4,4'-MDI); ▪ 4,4'-dibenzyl diisocyanate (4,4'-DBDI); ▪ 2,6-toluene diisocyanate (2,6-TDI); ▪ m-xylylene diisocyanate (m-XDI); ∘ symmetric alicyclic diisocyanate compounds, preferably methylene bis(4-cyclohexylisocyanate) (H12MDI); ∘ symmetric aliphatic diisocyanate compounds, preferably hexamethylene diisocyanate (HDI), pentamethylene diisocyanate (PDI); ∘ dissymmetric aromatic diisocyanate compounds, preferably: ▪ 2,4'-methylenediphenyl diisocyanate (2,4'-MDI); ▪ 2,4'-dibenzyl diisocyanate (2,4'-DBDI); ▪ 2,4-toluene diisocyanate (2,4-TDI); • the compound (B) is a trimer compound of biuret, in particular a trimer compound of biuret of a compound chosen among: ∘ symmetric aromatic diisocyanate compounds, preferably: ▪ 2,2'-methylenediphenyl diisocyanate (2,2'-MDI) and 4,4'-methylenediphenyl diisocyanate (4,4'-MDI); ▪ 4,4'-dibenzyl diisocyanate (4,4'-DBDI); ▪ 2,6-toluene diisocyanate (2,6-TDI); ▪ m-xylylene diisocyanate (m-XDI); o symmetric alicyclic diisocyanate compounds, preferably methylene bis(4-cyclohexylisocyanate) (H12MDI); o symmetric aliphatic diisocyanate compounds, preferably hexamethylene diisocyanate (HDI), pentamethylene diisocyanate (PDI); o dissymmetric aromatic diisocyanate compounds, preferably: ▪ 2,4'-methylenediphenyl diisocyanate (2,4'-MDI); ▪ 2,4'-dibenzyl diisocyanate (2,4'-DBDI); ▪ 2,4-toluene diisocyanate (2,4-TDI); • dissymmetric alicyclic diisocyanate compounds, preferably isophorone diisocyanate (IPDI).

6. The urethane compound according to one of claims 1 to 5, for which the compound (C) is a compound of formula (I) in which: • L independently represents an ethylene glycol residue; or • n represents a number ranging from 50 to 400, preferably from 100 to 300; or • L independently represents an ethylene glycol residue and n represents a number ranging from 50 to 400, preferably from 100 to 300.

7. The urethane compound according to one of claims 1 to 6, for which the compound of formula (I) has a molar mass (MW) ranging from 1,500 to 20,000 g / mol, preferably from 2,000 to 20,000 g / mol, more preferentially from 4,000 to 15,000 g / mol, determined as indicated in the description.

8. The urethane compound according to one of claims 1 to 7, for which the molar amount of compound (C) is around two times lower than the molar amount of monoisocyanate compound (A).

9. A method for preparing a urethane compound in the absence of any diisocyanate compound, by reaction: (A) of at least one monoisocyanate compound chosen among: (A1) a compound comprising a single isocyanate function and (A2) at least one monoisocyanate compound resulting from the separate reaction (A2-1) of at least one compound comprising at least one labile hydrogen atom and (A2-2) of at least one dissymmetric diisocyanate compound, (B) of at least one isocyanate compound comprising more than 2 isocyanate functions, and (C) of at least one compound of formula (I):         (HO)-Ln-(OH)     (I) in which L independently represents an alkylene glycol residue and n represents a number ranging from 40 to 400, the monoisocyanate compound being reacted with the alkylene glycol compound in the presence of the polyisocyanate compound.

10. The method according to claim 9 for preparing a urethane compound according to one of claims 1 to 8.

11. An aqueous composition comprising: • at least one compound chosen among a urethane compound according to one of claims 1 to 8 and a urethane compound prepared according to the method of claims 9 or 10, and optionally • at least one additive chosen among: ∘ an amphiphilic compound, in particular a surfactant compound, preferably a dihydroxylated surfactant compound, for example alkyl-polyalkylene glycol, in particular alkyl-polyethylene glycol and alkyl-polypropylene glycol; ∘ a polysaccharide derivative, for example cyclodextrin, cyclodextrin derivatives, polyethers; ∘ solvents, in particular coalescing solvents, and hydrotropic compounds, for example glycol, butylglycol, butyldiglycol, monopropylene glycol, ethylene glycol, ethylene diglycol, products whose CAS number is 34590-94-8, products whose CAS number is 25265-77-4; o anti-foaming agents, biocides.

12. An aqueous formulation comprising: • at least one composition according to claim 11; optionally • at least one organic or mineral pigment or organic, organometallic or mineral particles, for example calcium carbonate, talc, kaolin, mica, silicates, silica, metal oxides, in particular titanium dioxide, iron oxides; and optionally • at least one agent chosen among a particle spacing agent, a dispersing agent, a steric stabilising agent, an electrostatic stabilising agent, an opacifier, a solvent, a coalescent agent, an anti-foaming agent, a preservative, a biocide, a spreading agent, a thickening agent, a film-forming copolymer and mixtures thereof.

13. The coating formulation claim 12, in particular an ink formulation, a varnish formulation, an adhesive formulation, a paint formulation, for example a decorative paint or industrial paint formulation.

14. A concentrated aqueous pigment paste comprising at least one urethane compound according to one of claims 1 to 8 or at least one urethane compound prepared according to the method of claims 9 or 10 and at least one coloured organic or mineral pigment.

15. A method for controlling the viscosity of an aqueous composition comprising the addition of at least one urethane compound according to one of claims 1 to 8 or of at least one urethane compound prepared according to the method of claims 9 or 10; preferably method for controlling the viscosity for which the aqueous composition is a composition according to claim 11 or else a formulation defined according to one of claims 12 and 13.