Rheology-modified triurethane compounds

Abstract

The present invention relates to rheology-modified tricarbamate compounds. The present invention also provides aqueous compositions comprising the tricarbamate compounds of the present invention, and methods for controlling the viscosity of aqueous compositions using the tricarbamate compounds of the present invention.

Description

[0001] The present invention relates to rheology-modified tricarbamate compounds. The present invention also provides aqueous compositions comprising the tricarbamate compounds of the present invention, and methods for controlling the viscosity of aqueous compositions using the tricarbamate compounds of the present invention.

[0002] In general, for aqueous coating compositions, in particular aqueous paint or varnish compositions, it is necessary to control the viscosity at low or medium shear gradients and at high shear gradients. Indeed, during their preparation, storage, application or drying, paint formulations are subject to numerous stresses that require particularly complex rheological properties.

[0003] When paints are stored, pigment particles tend to settle by gravity. Therefore, paint formulations with high viscosities at very low shear gradients equivalent to the particle's terminal velocity are required to stabilize the dispersion of these pigment particles.

[0004] Paint uptake refers to the amount of paint picked up by an application tool, such as a paintbrush, brush, or roller. If a tool picks up a large amount of paint when it is dipped into and then removed from a paint can, frequent dipping can be avoided. Paint uptake increases with increasing viscosity. The equivalent shear gradient is calculated as a function of the paint flow rate for a specific thickness of paint on the tool. Therefore, a paint formulation should have a high viscosity even under low or moderate shear gradients.

[0005] Furthermore, the paint must have high filling properties so that a thick coat of paint is deposited with each stroke when applied to the substrate. High filling properties therefore enable a thicker wet film to be achieved with each stroke of the tool. Consequently, the paint formulation must have high viscosity under high shear gradients.

[0006] High viscosity under high shear gradients will also reduce or eliminate the risk of splashing or dripping when applying the paint.

[0007] The reduced viscosity under low or moderate shear gradients will also give the paint (especially single-coat paint) a neat, taut appearance after it is applied to the substrate. The substrate will then have a very uniform surface finish with no bumps or indentations. The final visual appearance of the dried coating is therefore greatly improved.

[0008] Furthermore, once the paint is applied to a surface, especially vertical surfaces, it should not flow. Therefore, the paint formulation needs to have high viscosity at low and moderate shear gradients. Finally, once the paint is applied to a surface, it should have high leveling capabilities. Therefore, the paint formulation must have reduced viscosity at low and moderate shear gradients.

[0009] HEUR (hydrophobically modified ethoxylated urethane) compounds are known as rheology modifiers. EP 0307775 discloses thickening polyurethane compounds for paint compositions prepared from diisocyanate compounds. FR 2372865 describes a combination of surfactants and polyurethanes for thickening textile printing pastes.

[0010] However, known HEUR compounds do not always offer a satisfactory solution. In particular, prior art rheology-modifying compounds do not always allow for effective viscosity control or are not always able to satisfactorily improve both Stormer viscosity (measured at low or moderate shear gradients, expressed in KU) and ICI viscosity (measured at high or very high shear gradients, expressed in s-1). In particular, known rheology-modifying compounds do not always increase the ICI viscosity / Stormer viscosity ratio.

[0011] Therefore, there is a need for improved rheology modifiers. The tricarbamate compounds according to the present invention make it possible to provide solutions to all or some of the problems of the rheology modifiers of the prior art. Therefore, the present invention provides a tricarbamate compound T prepared by reacting the following compounds:

[0012] a. one molar equivalent of at least one polyisocyanate compound (a) containing an average of three isocyanate groups and

[0013] b. one molar equivalent of at least one polyalkoxylated compound (b) selected from the group consisting of:

[0014] - linear aliphatic monools (b1) containing 6 to 40 polyalkoxylated carbon atoms,

[0015] - branched aliphatic monools (b2) containing 6 to 40 polyalkoxylated carbon atoms,

[0016] - cycloaliphatic monools (b3) containing 6 to 40 polyalkoxylated carbon atoms,

[0017] - monoaromatic monools (b4) containing 6 to 30 polyalkoxylated carbon atoms,

[0018] - a polyaromatic monool (b5) containing 10 to 80 polyalkoxylated carbon atoms, and

[0019] c. two molar equivalents of at least two identical or different compounds (c) selected from the group consisting of:

[0020] - linear aliphatic monohydric alcohols (c1) containing 6 to 40 polyalkoxylated carbon atoms,

[0021] - branched aliphatic monoalcohols (c2) containing 6 to 40 polyalkoxylated carbon atoms,

[0022] - cycloaliphatic monools containing 6 to 40 polyalkoxylated carbon atoms (c3),

[0023] - monoaromatic monoalcohols containing 6 to 30 polyalkoxylated carbon atoms (c4),

[0024] - polyaromatic monools (c5) containing 10 to 80 polyalkoxylated carbon atoms,

[0025] - linear aliphatic monoalcohols containing 6 to 40 non-alkoxylated carbon atoms (c6),

[0026] - branched aliphatic monoalcohols containing 6 to 40 non-alkoxylated carbon atoms (c7),

[0027] - cycloaliphatic monoalcohols containing 6 to 40 non-alkoxylated carbon atoms (c8),

[0028] - monoaromatic monoalcohols containing 6 to 30 non-alkoxylated carbon atoms (c9),

[0029] - polyaromatic monools containing from 10 to 80 non-alkoxylated carbon atoms (c10).

[0030] Basically, according to the present invention, a tricarbamate compound T is prepared from at least one compound (a) containing three isocyanate groups and at least one, at least two or at least three compounds (b) capable of reacting with these isocyanate groups, wherein the tricarbamate compound T comprises a saturated, unsaturated or aromatic hydrocarbon chain bonded to a polyalkoxylated chain. Preferably, according to the present invention, the reagent compound is a monohydroxy compound. In addition to the tricarbamate compound T, the present invention also provides several other specific tricarbamate compounds that share these essential features with the compound T according to the present invention. These tricarbamate compounds Ta, Tb and Tc according to the present invention comprise three, two or one polyalkoxylated chains, respectively.

[0031] Therefore, the present invention provides a tricarbamate compound Ta comprising three polyalkoxylated chains. The tricarbamate compound Ta according to the present invention is prepared by reacting the following compounds:

[0032] a. one molar equivalent of at least one triisocyanate compound (a) and

[0033] b. one molar equivalent of at least one polyalkoxylated compound (b) selected from the group consisting of:

[0034] - linear aliphatic monools (b1) containing 6 to 40 polyalkoxylated carbon atoms,

[0035] - branched aliphatic monools (b2) containing 6 to 40 polyalkoxylated carbon atoms,

[0036] - cycloaliphatic monools (b3) containing 6 to 40 polyalkoxylated carbon atoms,

[0037] - monoaromatic monools (b4) containing 6 to 30 polyalkoxylated carbon atoms,

[0038] - polyaromatic monools (b5) containing 10 to 80 polyalkoxylated carbon atoms,

[0039] c. two molar equivalents of at least one polyalkoxylated compound (c) selected from the group consisting of the same or different compounds:

[0040] - linear aliphatic monohydric alcohols (c1) containing 6 to 40 polyalkoxylated carbon atoms,

[0041] - branched aliphatic monoalcohols (c2) containing 6 to 40 polyalkoxylated carbon atoms,

[0042] - cycloaliphatic monools containing 6 to 40 polyalkoxylated carbon atoms (c3),

[0043] - monoaromatic monoalcohols containing 6 to 30 polyalkoxylated carbon atoms (c4),

[0044] - polyaromatic monools containing 10 to 80 polyalkoxylated carbon atoms (c5).

[0045] Preferably, according to the present invention, the linear polyalkoxylated aliphatic monoalcohol (b1) used to prepare the tricarbamate compound Ta contains 80 to 500 alkoxy groups. Also preferably, according to the present invention, the monoaromatic polyalkoxylated alcohol (b4) used to prepare the tricarbamate compound Ta contains 6 to 12 carbon atoms or 22 to 30 carbon atoms.

[0046] Therefore, the present invention also provides a tricarbamate compound Tb comprising two polyalkoxylated chains and one non-alkoxylated chain. The tricarbamate compound Tb according to the present invention is prepared by reacting the following compounds:

[0047] a. one molar equivalent of at least one triisocyanate compound (a) and

[0048] b. one molar equivalent of at least one polyalkoxylated compound (b) selected from the group consisting of:

[0049] - linear aliphatic monools (b1) containing 6 to 40 polyalkoxylated carbon atoms,

[0050] - branched aliphatic monools (b2) containing 6 to 40 polyalkoxylated carbon atoms,

[0051] - cycloaliphatic monools (b3) containing 6 to 40 polyalkoxylated carbon atoms,

[0052] - monoaromatic monools (b4) containing 6 to 30 polyalkoxylated carbon atoms,

[0053] - polyaromatic monools (b5) containing 10 to 80 polyalkoxylated carbon atoms,

[0054] c. one molar equivalent of at least one polyalkoxylated compound (c) selected from the group consisting of the same or different compounds:

[0055] - linear aliphatic monohydric alcohols (c1) containing 6 to 40 polyalkoxylated carbon atoms,

[0056] - branched aliphatic monoalcohols (c2) containing 6 to 40 polyalkoxylated carbon atoms,

[0057] - cycloaliphatic monools containing 6 to 40 polyalkoxylated carbon atoms (c3),

[0058] - monoaromatic monoalcohols containing 6 to 30 polyalkoxylated carbon atoms (c4),

[0059] - polyaromatic monools (c5) containing 10 to 80 polyalkoxylated carbon atoms,

[0060] One molar equivalent of at least one non-alkoxylated compound (c) selected from the group consisting of the same or different compounds:

[0061] - linear aliphatic monoalcohols containing 6 to 40 non-alkoxylated carbon atoms (c6),

[0062] - branched aliphatic monoalcohols containing 6 to 40 non-alkoxylated carbon atoms (c7),

[0063] - cycloaliphatic monoalcohols containing 6 to 40 non-alkoxylated carbon atoms (c8),

[0064] - monoaromatic monoalcohols containing 6 to 30 non-alkoxylated carbon atoms (c9),

[0065] - polyaromatic monools containing from 10 to 80 non-alkoxylated carbon atoms (c10).

[0066] Preferably, according to the invention, the linear, non-alkoxylated, aliphatic monool (c6) used for the preparation of the tricarbamate compound Tb comprises from 16 to 40 carbon atoms.

[0067] Therefore, the present invention also provides a tricarbamate compound Tc comprising a polyalkoxylated chain and two non-alkoxylated chains. The tricarbamate compound Tc of the present invention is prepared by reacting the following compounds:

[0068] a. one molar equivalent of at least one triisocyanate compound (a) and

[0069] b. a molar equivalent of at least one polyalkoxylated compound (b) selected from the group consisting of the same or different compounds:

[0070] - linear aliphatic monools (b1) containing 6 to 40 polyalkoxylated carbon atoms,

[0071] - branched aliphatic monools (b2) containing 6 to 40 polyalkoxylated carbon atoms,

[0072] - cycloaliphatic monools (b3) containing 6 to 40 polyalkoxylated carbon atoms,

[0073] - monoaromatic monools (b4) containing 6 to 30 polyalkoxylated carbon atoms,

[0074] - polyaromatic monools (b5) containing 10 to 80 polyalkoxylated carbon atoms,

[0075] c. two molar equivalents of at least one non-alkoxylated compound (c) selected from the group consisting of the same or different compounds:

[0076] - linear aliphatic monoalcohols containing 6 to 40 non-alkoxylated carbon atoms (c6),

[0077] - branched aliphatic monoalcohols containing 6 to 40 non-alkoxylated carbon atoms (c7),

[0078] - cycloaliphatic monoalcohols containing 6 to 40 non-alkoxylated carbon atoms (c8),

[0079] - monoaromatic monoalcohols containing 6 to 30 non-alkoxylated carbon atoms (c9),

[0080] - polyaromatic monools containing from 10 to 80 non-alkoxylated carbon atoms (c10).

[0081] According to the invention, the monohydric alcohols used to prepare the tricarbamate compounds according to the invention contain hydrocarbon groups. The number of carbon atoms in these monohydric alcohols corresponds to the carbon atoms in these hydrocarbon groups, excluding the carbon atoms in the alkoxy groups.

[0082] Preferably, according to the present invention, the condensation of compounds a, b and c is carried out in the presence of a catalyst. The catalyst can be selected from amines, preferably 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), metal derivatives selected from Al, Bi, Sn, Hg, Pb, Mn, Zn, Zr, Ti. Trace amounts of water may also participate in the catalysis of the reaction. As examples of metal derivatives, preferably dibutylbismuth dilaurate, dibutylbismuth diacetate, dibutylbismuth oxide, bismuth carboxylate, dibutyltin dilaurate, dibutyltin diacetate, derivatives of dibutyltin oxide, mercury derivatives, lead derivatives, zinc salts, manganese salts, compounds comprising zirconium chelates, compounds comprising aluminum chelates. Preferred metal derivatives are selected from Bi derivatives, Sn derivatives and Ti derivatives.

[0083] Preferably, according to the present invention, a single compound (a) is used in the reaction or two or three different compounds (a) are used in the reaction. According to the present invention, the polyisocyanate compound (a) comprises an average of three isocyanate groups. Typically, the polyisocyanate compound (a) comprises an average of 3±10% molar isocyanate groups. Preferably, according to the present invention, the compound (a) is selected from:

[0084] Triphenylmethane-4,4',4"-triisocyanate or 1,1',1"-methylenetris(4-isocyanatobenzene);

[0085] o Isocyanurate compounds, in particular isocyanurate compounds derived from compounds selected from the group consisting of:

[0086] ■Symmetrical aromatic diisocyanate compounds, preferably:

[0087] 2,2'-diphenylmethylene diisocyanate (2,2'-MDI) and 4,4'-diphenylmethylene diisocyanate (4,4'-MDI);

[0088] 4,4'-dibenzyl diisocyanate (4,4'-DBDI);

[0089] 2,6-Toluene diisocyanate (2,6-TDI);

[0090] ●m-Xylylenediisocyanate (m-XDI);

[0091] ■ Symmetrical alicyclic diisocyanate compounds, preferably methylenebis(4-cyclohexyl isocyanate)(H 12 MDI);

[0092] ■ Symmetrical aliphatic diisocyanate compounds, preferably hexamethylene diisocyanate (HDI) and pentamethylene diisocyanate (PDI);

[0093] ■Asymmetric aromatic diisocyanate compounds, preferably:

[0094] 2,4'-diphenylmethylene diisocyanate (2,4'-MDI);

[0095] 2,4'-dibenzyl diisocyanate (2,4'-DBDI);

[0096] 2,4-Toluene diisocyanate (2,4-TDI);

[0097] o Biuret trimer compounds, in particular biuret trimer compounds derived from compounds selected from:

[0098] ■Symmetrical aromatic diisocyanate compounds, preferably:

[0099] 2,2'-diphenylmethylene diisocyanate (2,2'-MDI) and 4,4'-diphenylmethylene diisocyanate (4,4'-MDI);

[0100] 4,4'-dibenzyl diisocyanate (4,4'-DBDI);

[0101] 2,6-Toluene diisocyanate (2,6-TDI);

[0102] ●m-Xylylenediisocyanate (m-XDI);

[0103] ■ A symmetrical alicyclic diisocyanate compound, preferably methylene bis(4-cyclohexyl isocyanate) (H12MDI);

[0104] ■ Symmetrical aliphatic diisocyanate compounds, preferably hexamethylene diisocyanate (HDI) and pentamethylene diisocyanate (PDI);

[0105] ■Asymmetric aromatic diisocyanate compounds, preferably:

[0106] 2,4'-diphenylmethylene diisocyanate (2,4'-MDI);

[0107] 2,4'-dibenzyl diisocyanate (2,4'-DBDI);

[0108] ●2,4-Toluene diisocyanate (2,4-TDI).

[0109] According to the present invention, compound (a) is preferably selected from triphenylmethane-4,4',4"-triisocyanate, 1,1',1"-methylenetris(4-isocyanatebenzene), HDI isocyanurate, IPDI isocyanurate, PDI isocyanurate, HDI biuret trimer and IPDI biuret trimer, PDI biuret trimer and combinations thereof.

[0110] According to the invention, a monoalcohol is a compound containing a terminal monohydroxyl group (OH). According to the invention, a polyalkoxylated monoalcohol is a compound containing a hydrocarbon chain containing a plurality of alkoxy groups and a terminal hydroxyl group (OH). According to the invention, a polyalkoxylated monoalcohol is a compound of the formula R-(LO) n -H, wherein R represents a hydrocarbon chain, n represents the number of polyalkoxylations, and L is the same or different and independently represents a linear or branched alkylene group containing 1 to 4 carbon atoms. According to the present invention, a non-alkoxylated monoalcohol is a compound containing a hydrocarbon chain and a terminal monohydroxyl group (OH). According to the present invention, a non-alkoxylated monoalcohol is a compound of the formula R'-OH, wherein R' represents a hydrocarbon chain. Preferably, according to the present invention, the polyalkoxylated monoalcohol contains 2 to 500 alkoxy groups, preferably 80 to 400 alkoxy groups or 100 to 200 alkoxy groups. Also preferably, according to the present invention, the alkoxy group is selected from ethylene oxide (-CH2CHO-), propylene oxide (-CH2CH(CH3)O- or -CH(CH3)CHO-), butylene oxide (-CH(CH2CH3)CHO- or -CH2CH(CH2CH3)O-), and combinations thereof. More preferably, the alkoxy group is ethylene oxide alone or in combination with propylene oxide, especially comprising propylene oxide in an amount of 1 to 30% by moles.Very more preferably, the alkoxy group is ethylene oxide.

[0111] Essentially, according to the invention, compounds T, Ta, Tb, and Tc are compounds containing alkoxy groups. Preferably, according to the invention, the degree of polyalkoxylation of compounds T, Ta, Tb, and Tc is from 100 to 500 alkoxy groups or from 100 to 502 alkoxy groups. The degree of polyalkoxylation defines the number of alkoxy groups, in particular the number of ethylene oxide, propylene oxide, or butylene oxide, contained in these compounds.

[0112] According to the present invention, compound (b) is as follows:

[0113] The hydrocarbon chain of the monohydric alcohol (b1) contains 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms or 8 to 16 carbon atoms. More preferably, the monohydric alcohol (b1) is selected from polyalkoxylated n-octanol, polyalkoxylated n-decanol, polyalkoxylated n-dodecanol, polyalkoxylated n-hexadecanol, or

[0114] The hydrocarbon chain of the monohydric alcohol (b2) comprises 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms or 8 to 16 carbon atoms, more preferably, the monohydric alcohol (b2) is selected from polyalkoxylated ethylhexanol, polyalkoxylated isooctyl alcohol, polyalkoxylated isononyl alcohol, polyalkoxylated isodecanol, polyalkoxylated propylheptanol, polyalkoxylated butyloctanol, polyalkoxylated isododecanol, polyalkoxylated isohexadecanol, polyalkoxylated oxyalcohol, polyalkoxylated Guerbet alcohol, or

[0115] The hydrocarbon chain of the monohydric alcohol (b3) contains 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms or 8 to 20 carbon atoms, more preferably, the monohydric alcohol (b3) is selected from polyalkoxylated ethylcyclohexanol, polyalkoxylated n-nonylcyclohexanol or polyalkoxylated n-dodecylcyclohexanol, or

[0116] The hydrocarbon chain of the monohydric alcohol (b4) contains 12 to 30 carbon atoms or 12 to 22 carbon atoms. More preferably, the monohydric alcohol (b4) is selected from polyalkoxylated n-pentadecylphenol, or

[0117] The hydrocarbon chain of the monoalcohol (b5) contains 10 to 60 carbon atoms. Preferably, the monoalcohol (b5) is selected from polyalkoxylated naphthols, polyalkoxylated distyrylphenols, polyalkoxylated tristyrylphenols and polyalkoxylated pentastyrylcumylphenols.

[0118] More preferably, according to the invention, the hydrocarbon chain of the monoalcohol (b4) of the tricarbamate Tb or Tc comprises 12 to 30 carbon atoms or 12 to 22 carbon atoms, more preferably, the monoalcohol (b4) is chosen from polyalkoxylated n-pentadecylphenol.

[0119] According to the present invention, compound (c) is as follows:

[0120] The hydrocarbon chain of the monohydric alcohol (c1) contains 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms or 8 to 16 carbon atoms. More preferably, the monohydric alcohol (c1) is selected from polyalkoxylated n-octanol, polyalkoxylated n-decanol, polyalkoxylated n-dodecanol, polyalkoxylated n-hexadecanol, or

[0121] The hydrocarbon chain of the monohydric alcohol (c2) comprises 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms or 8 to 16 carbon atoms, more preferably, the monohydric alcohol (c2) is selected from polyalkoxylated ethylhexanol, polyalkoxylated isooctyl alcohol, polyalkoxylated isononyl alcohol, polyalkoxylated isodecanol, polyalkoxylated propylheptanol, polyalkoxylated butyloctanol, polyalkoxylated isododecanol, polyalkoxylated isohexadecanol, polyalkoxylated oxyalcohol, polyalkoxylated Guerbet alcohol, or

[0122] The hydrocarbon chain of the monohydric alcohol (c3) contains 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms or 8 to 20 carbon atoms, more preferably, the monohydric alcohol (c3) is selected from polyalkoxylated ethylcyclohexanol, polyalkoxylated n-nonylcyclohexanol or polyalkoxylated n-dodecylcyclohexanol, or

[0123] The hydrocarbon chain of the monohydric alcohol (c4) contains 12 to 30 carbon atoms or 12 to 22 carbon atoms, more preferably, the monohydric alcohol (c4) is selected from polyalkoxylated n-pentadecylphenol, or

[0124] the hydrocarbon chain of the monohydric alcohol (c5) comprises from 10 to 60 carbon atoms, preferably the monohydric alcohol (c5) is selected from polyalkoxylated naphthols, polyalkoxylated distyrylphenols, polyalkoxylated tristyrylphenols and polyalkoxylated pentastyrylcumylphenols,

[0125] The hydrocarbon chain of the monohydric alcohol (c6) contains 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms or 8 to 16 carbon atoms, more preferably, the monohydric alcohol (c6) is selected from non-alkoxylated n-octanol, non-alkoxylated n-decanol, non-alkoxylated n-dodecanol, non-alkoxylated n-hexadecanol, or

[0126] The hydrocarbon chain of the monohydric alcohol (c7) comprises 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms or 8 to 16 carbon atoms, more preferably, the monohydric alcohol (c7) is selected from non-alkoxylated ethylhexanol, non-alkoxylated isooctyl alcohol, non-alkoxylated isononyl alcohol, non-alkoxylated isodecanol, non-alkoxylated propylheptanol, non-alkoxylated butyloctanol, non-alkoxylated isododecanol, non-alkoxylated isohexadecanol, non-alkoxylated oxo alcohols, non-alkylated Guerbet alcohols, or

[0127] The hydrocarbon chain of the monohydric alcohol (c8) contains 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms or 8 to 20 carbon atoms, more preferably, the monohydric alcohol (c8) is selected from non-alkoxylated ethylcyclohexanol, non-alkoxylated n-nonylcyclohexanol or non-alkoxyalkylated n-dodecylcyclohexanol, or

[0128] The hydrocarbon chain of the monohydric alcohol (c9) contains 12 to 30 carbon atoms or 12 to 22 carbon atoms, more preferably, the monohydric alcohol (c9) is selected from non-alkoxylated n-pentadecylphenol, or

[0129] The hydrocarbon chain of the monoalcohol (C10) comprises 10 to 60 carbon atoms, preferably, the monoalcohol (C10) is selected from non-alkoxylated naphthol, non-alkoxylated distyrylphenol, non-alkoxylated tristyrylphenol and non-alkoxylated pentastyrylcumylphenol. More preferably, according to the present invention, the hydrocarbon chain of the monoalcohol (C6) of the tricarbamate Ta or Tc comprises 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms or 8 to 16 carbon atoms, more preferably, the monoalcohol (C6) is selected from non-alkoxylated n-octanol, non-alkoxylated n-decanol, non-alkoxylated n-dodecanol, non-alkoxylated n-hexadecanol.

[0130] Therefore, the present invention relates to compounds T, Ta, Tb and Tc, which do not include

[0131] - one molar equivalent of triisocyanate (toluene diisocyanate-trimethylolpropane, marketed as Mondur CB-75 or 1,6-hexamethylene diisocyanate trimer, marketed as Desmodur N) and three molar equivalents of nC 12 H 25 - a tricarbamate compound obtained by condensing an alkyl group and 55 ethoxylated aliphatic monohydric alcohols,

[0132] - a tricarbamate compound obtained by condensing one molar equivalent of a triisocyanate (toluene diisocyanate-trimethylolpropane, marketed as Mondur CB-75 or 1,6-hexamethylene diisocyanate trimer, marketed as Desmodur N) and three molar equivalents of an aromatic monool containing a tert-octyl-phenyl group and 166 ethoxylated groups,

[0133] - is composed of one molar equivalent of triisocyanate (toluene diisocyanate-trimethylolpropane, marketed as Mondur CB-75 or 1,6-hexamethylene diisocyanate trimer, marketed as Desmodur N) and two molar equivalents of n-C8H 17 -alkyl and 162 ethoxylated aliphatic monoalcohols and one molar equivalent of n-C8H 17 -alkyl non-alkoxylated aliphatic monohydric alcohol condensation tricarbamate compound,

[0134] - one molar equivalent of triisocyanate (toluene diisocyanate-trimethylolpropane, marketed as Mondur CB-75 or 1,6-hexamethylene diisocyanate trimer, marketed as Desmodur N) and two molar equivalents of nC 12 H 25 -alkyl and 162 ethoxylated aliphatic monoalcohols and one molar equivalent of nC 12 H25 -alkyl non-alkoxylated aliphatic monohydric alcohol condensation tricarbamate compound,

[0135] - a mixture of one molar equivalent of triisocyanate (toluene diisocyanate-trimethylolpropane, marketed as Mondur CB-75 or 1,6-hexamethylene diisocyanate trimer, marketed as Desmodur N) and three molar equivalents of C 12 -phenyl and 135 ethoxylated aromatic monohydric alcohol condensation obtained by tricarbamate compound.

[0136] In addition to the tricarbamate compound T, the present invention also relates to a method for preparing the compound. Therefore, the present invention provides a method for preparing the tricarbamate compound T by reacting the following compounds:

[0137] a. one molar equivalent of at least one polyisocyanate compound (a) containing an average of three isocyanate groups and

[0138] b. one molar equivalent of at least one polyalkoxylated compound (b) selected from the group consisting of:

[0139] - linear aliphatic monools (b1) containing 6 to 40 polyalkoxylated carbon atoms,

[0140] - branched aliphatic monools (b2) containing 6 to 40 polyalkoxylated carbon atoms,

[0141] - cycloaliphatic monools (b3) containing 6 to 40 polyalkoxylated carbon atoms,

[0142] - monoaromatic monools (b4) containing 6 to 30 polyalkoxylated carbon atoms,

[0143] - polyaromatic monools (b5) containing 10 to 80 polyalkoxylated carbon atoms,

[0144] c. two molar equivalents of at least two identical or different compounds (c) selected from the group consisting of:

[0145] linear aliphatic monoalcohols (c1) containing 6 to 40 polyalkoxylated carbon atoms,

[0146] branched aliphatic monoalcohols (c2) containing 6 to 40 polyalkoxylated carbon atoms,

[0147] cycloaliphatic monoalcohols (c3) containing 6 to 40 polyalkoxylated carbon atoms,

[0148] monoaromatic monoalcohols (c4) containing 6 to 30 polyalkoxylated carbon atoms,

[0149] polyaromatic monools (c5) containing 10 to 80 polyalkoxylated carbon atoms,

[0150] linear aliphatic monoalcohols containing from 6 to 40 non-alkoxylated carbon atoms (c6),

[0151] Branched aliphatic monoalcohols containing 6 to 40 non-alkoxylated carbon atoms (c7),

[0152] cycloaliphatic monoalcohols containing 6 to 40 non-alkoxylated carbon atoms (c8),

[0153] monoaromatic monoalcohols containing 6 to 30 non-alkoxylated carbon atoms (c9),

[0154] • Polyaromatic monools containing from 10 to 80 non-alkoxylated carbon atoms (c10).

[0155] Similarly, the present invention provides a process for preparing the preferred triurethane T compounds according to the invention or for preparing the triurethane compounds Ta, Tb and Tc according to the invention, respectively.

[0156] Preferably, according to the present invention, for the preparation method according to the present invention, the condensation of compounds a, b and c is carried out in the presence of a catalyst. More preferably, the reaction is catalyzed by an amine, preferably 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), or at least one metal derivative selected from Al, Bi, Sn, Hg, Pb, Mn, Zn, Zr, Ti. Trace amounts of water may also participate in the catalysis of the reaction. As examples of metal derivatives, preferably dibutylbismuth dilaurate, dibutylbismuth diacetate, dibutylbismuth oxide, bismuth carboxylate, dibutyltin dilaurate, dibutyltin diacetate, derivatives of dibutyltin oxide, mercury derivatives, lead derivatives, zinc salts, manganese salts, compounds comprising zirconium chelates, compounds comprising aluminum chelates. Preferred metal derivatives are selected from Bi derivatives, Sn derivatives and Ti derivatives.

[0157] Advantageously, according to the present invention, the condensation of compounds a, b and c is carried out in an organic solvent. Preferred organic solvents are solvents that do not react with the isocyanate groups of compound a, in particular selected from hydrocarbon solvents (in particular C8 to C 30 More preferably, according to the present invention, the condensation is carried out directly with different reagents or in toluene.

[0158] At the end of the preparation of the compound T according to the invention, a solution of the compound in an organic solvent is obtained. This solution can be used directly. According to the invention, the organic solvent can also be separated and the compound T can be dried. The dried compound T according to the invention can be used in solid form, for example in the form of a powder or granules.

[0159] In addition to the tricarbamate compounds T, Ta, Tb and Tc and the process for preparing these compounds, the present invention also relates to an aqueous composition comprising at least one tricarbamate compound according to the invention. The present invention also relates to an aqueous composition comprising at least one tricarbamate compound prepared by the process for preparing the same according to the invention.

[0160] Advantageously, the carbamate compound according to the present invention is an essentially hydrophilic compound and can be formulated in an aqueous medium.

[0161] The aqueous composition according to the invention may also comprise at least one additive, in particular an additive chosen from:

[0162] amphiphilic compounds, in particular surfactant compounds, preferably hydroxylated surfactant compounds, such as alkylpolyalkylene glycols, in particular alkylpolyethylene glycol and alkylpolypropylene glycol;

[0163] Polysaccharide derivatives, such as cyclodextrins, cyclodextrin derivatives, polyethers, alkyl glycosides;

[0164] Solvents, in particular coalescing solvents and hydrotropic compounds, such as glycols, butyl glycol, butyl diglycol, monopropylene glycol, ethylene glycol, diethylene glycol, Dowanol products with CAS number 34590-94-8, Texanol products with CAS number 25265-77-4;

[0165] ●Defoaming agent, biocide.

[0166] The present 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 also comprise at least one organic or mineral pigment or organic, organometallic or mineral particles, such as calcium carbonate, talc, kaolin, mica, silicates, silicon dioxide, metal oxides, in particular titanium dioxide, iron oxides. The aqueous formulation according to the invention may also comprise at least one agent selected from particle spacers, dispersants, steric stabilizers, electrostatic stabilizers, opacifiers, solvents, coalescing agents, defoamers, preservatives, biocides, spreading agents, thickeners, film-forming copolymers, and mixtures thereof.

[0167] Depending on the specific carbamate compound or the additives it contains, the formulations according to the invention can be used in a variety of technical fields. Thus, the formulations according to the invention can be coating formulations. Preferably, the formulations according to the invention are ink formulations, adhesive formulations, varnish formulations, paint formulations, such as decorative paints or industrial paints. Preferably, the formulations according to the invention are paint formulations.

[0168] The present invention also provides concentrated water-based pigment slurries comprising at least one urethane compound according to the invention and at least one colored organic or mineral pigment.

[0169] The tricarbamate compounds according to the present invention have properties that make them useful for modifying or controlling the rheology of a medium in which they are contained.Thus, the present invention also provides a method for controlling the viscosity of an aqueous composition.

[0170] The viscosity control method according to the present invention comprises adding at least one tricarbamate compound according to the present invention to an aqueous composition. This viscosity control method may also comprise adding at least one tricarbamate compound prepared according to the preparation method of the present invention.

[0171] Preferably, the viscosity control method according to the invention is performed using an aqueous composition according to the invention. Also preferably, the viscosity control method according to the invention is performed using an aqueous formulation according to the invention.

[0172] The aqueous composition according to the invention, the preparation according to the invention, the pigment paste and the viscosity control method are defined by specific, advantageous or preferred features of the tricarbamate compound T according to the invention, which are also specific, advantageous or preferred.

[0173] The following examples illustrate various aspects of the invention.

[0174] Example 1: Preparation of carbamate compounds according to the present invention

[0175] Example 1-1: Preparation of compound Ta1 according to the present invention

[0176] In a 3 L glass reactor equipped with a mechanical stirring rod, a vacuum pump and a nitrogen inlet, heated by a double jacket in which oil circulates, 450.3 g of a dodecanol / tetradecanol blend ethoxylated with 140 mol of ethylene oxide (MM=6355 Da) are introduced and heated to 90° C. in an inert atmosphere. The product is dehydrated.

[0177] Then, under stirring and in an inert atmosphere, 12.97 g of HDI isocyanurate (average MM = 549 g / mol) is added over 1 hour in the presence of 200 ppm of bismuth carboxylate catalyst. After the addition is complete, the reaction mixture is stirred at 90°C ± 1°C for 60 minutes. The presence of isocyanate is then checked by back titration. 1 g is collected from the reaction medium, to which an excess of dibutylamine (e.g., 1 mol) is added, which reacts with any isocyanate groups present in the medium. The unreacted dibutylamine is then analyzed with hydrochloric acid (e.g., 1 N). The number of isocyanate groups present in the reaction medium can then be deduced from this. If this value is not zero, the reaction is continued for 15 minutes until the reaction is complete. When the level reaches zero, a tricarbamate compound Ta1 is formulated using a surfactant compound such as an ethoxylated alcohol (ethoxylated n-octanol with ten ethylene oxide equivalents), 1000 ppm of a biocide (Biopol SMV Chemipol), and 1000 ppm of a defoamer (Tego 1488 Evonik). A composition consisting of 20% by mass of the compound of the present invention, 5% by mass of a surfactant, and 75% by mass of water was obtained.

[0178] Example 1-2: Preparation of compound Tb1 according to the present invention

[0179] In a 3 L glass reactor equipped with a mechanical stirring rod, a vacuum pump and a nitrogen inlet, 448.7 g of a dodecanol / tetradecanol blend ethoxylated with 140 mol of ethylene oxide (MM=6355 Da) are introduced by means of a double jacket heating in which oil is circulated and heated to 90° C. in an inert atmosphere. The product is dehydrated.

[0180] Then under stirring and in an inert atmosphere, 6.57g of dodecanol was quickly added, and then 19.38g of HDI isocyanurate (average MM=549 g / mol g / mol) was added in the presence of 200ppm of bismuth carboxylate catalyst within 1 hour. After the addition was completed, the reaction mixture was stirred at 90°C ± 1°C for 60 minutes. As described in Example 1-1-1, the presence or absence of isocyanate was checked by back titration. If the numerical value is not zero, the reaction continues for 15 minutes until the reaction is complete. When the level reaches zero, the tricarbamate compound Tb1 obtained by preparing the surfactant compound, biocide and defoamer of Example 1-1 is used. A composition consisting of 20% by mass of the compound of the present invention, 5% by mass of the surfactant and 75% by mass of water was obtained.

[0181] Examples 1-3: Preparation of compound Tb2 according to the present invention

[0182] In a 3 L glass reactor equipped with a mechanical stirring rod, a vacuum pump and a nitrogen inlet, 348.6 g of a dodecanol / tetradecanol blend ethoxylated with 140 mol of ethylene oxide (MM=6355 Da) and 82.61 g of dodecanol ethoxylated with 30 mol of ethylene oxide (MM=1506 g / mol) were introduced by means of a double jacket heating in which oil was circulated and heated to 90° C. in an inert atmosphere. These products were dehydrated.

[0183] Then under stirring and in an inert atmosphere, 10.20g of dodecanol is added quickly, and then 30.12g of HDI isocyanurate (average MM=549 grams / mole) is added in the presence of 200ppm of bismuth carboxylate catalyst within 1 hour. After the addition is completed, the reaction mixture is stirred at 90°C ± 1°C for 60 minutes. As described in Example 1-1, the presence or absence of isocyanate is checked by back titration. If the numerical value is not zero, the reaction continues for 15 minutes until the reaction is complete. When the level reaches zero, the tricarbamate compound Tb2 obtained is prepared in water together with the biocide and defoamer of Example 1-1. The composition consisting of 20% by mass of the compound of this invention and 80% by mass of water is obtained.

[0184] Examples 1-4: Preparation of compound Tc1 according to the present invention

[0185] In a 3 L glass reactor equipped with a mechanical stirring rod, a vacuum pump and a nitrogen inlet, and heated by a double jacket in which oil circulates, 415.1 g of a dodecanol / tetradecanol blend ethoxylated with 140 mol of ethylene oxide (MM=6355 Da) are introduced. This product is dehydrated.

[0186] Then under stirring and in an inert atmosphere, 24.30g of dodecanol was quickly added, and then 35.86g of HDI isocyanurate (average MM=549 g / mol) was added in the presence of 200ppm of bismuth carboxylate catalyst within 1 hour. After the addition was completed, the reaction mixture was stirred at 90°C ± 1°C for 60 minutes. As described in Example 1-1, the presence or absence of isocyanate was checked by back titration. If the numerical value is not zero, the reaction continues for 15 minutes until the reaction is complete. When the level reaches zero, the tricarbamate compound Tc1 obtained is prepared in water together with the biocide and defoamer of Example 1-1. A composition consisting of 20% by mass of the compound of the present invention and 80% by mass of water is obtained.

[0187] Examples 1-5: Preparation of compound Ta2 according to the present invention

[0188] In a 3 L glass reactor equipped with a mechanical stirring rod, a vacuum pump and a nitrogen inlet, 398.9 g of a dodecanol / tetradecanol blend ethoxylated with 140 mol of ethylene oxide (MM=6355 Da) and 47.27 g of dodecanol ethoxylated with 30 mol of ethylene oxide (MM=1506 g / mol) were introduced by means of a double jacket heating in which oil was circulated and heated to 90° C. in an inert atmosphere. The blend was dehydrated.

[0189] Then under stirring and in an inert atmosphere, 17.23g HDI isocyanurate (average MM=549 g / mol) was added in the presence of 200ppm bismuth carboxylate catalyst within 1 hour. After the addition was completed, the reaction mixture was stirred at 90°C ± 1°C for 60 minutes. As described in Example 1-1, the presence of isocyanate was checked by back titration. If the numerical value is not zero, the reaction continues for 15 minutes until the reaction is complete. When the level reaches zero, the tricarbamate compound Ta2 obtained by the surfactant compound, biocide and defoamer formulation of Example 1-1 is used. A composition consisting of 20% by mass of the compound of the present invention, 5% by mass of the surfactant and 75% by mass of water is obtained.

[0190] Examples 1-6: Preparation of compound Ta3 according to the present invention

[0191] In a 3 L glass reactor equipped with a mechanical stirrer, a vacuum pump and a nitrogen inlet, and heated by a double jacket with oil circulation, 440.6 g of tristyrylphenol ethoxylated with 130 mol of ethylene oxide (MM=6120 Da) are introduced and heated to 90° C. in an inert atmosphere. The product is dehydrated.

[0192] Then under stirring and in an inert atmosphere, 13.17g HDI isocyanurate (average MM=549 mol / mol) was added in the presence of 200ppm bismuth carboxylate catalyst within 1 hour. After the addition was completed, the reaction mixture was stirred at 90°C ± 1°C for 60 minutes. As described in Example 1-1, the presence of isocyanate was checked by back titration. If the numerical value is not zero, the reaction is continued for 15 minutes until the reaction is complete. When the level reaches zero, the tricarbamate compound Ta3 obtained is prepared in water together with the biocide and defoamer of Example 1-1. A composition consisting of 20% by mass of the compound of the present invention and 80% by mass of water is obtained.

[0193] Examples 1-7: Preparation of compound Ta4 according to the present invention

[0194] In a 3 L glass reactor equipped with a mechanical stirring rod, a vacuum pump and a nitrogen inlet, 440.6 g of a dodecanol / tetradecanol blend ethoxylated with 130 mol of ethylene oxide (MM=6355 Da) are introduced by means of a double jacket heating in which oil is circulated and heated to 90° C. in an inert atmosphere. The product is dehydrated.

[0195] Then, under stirring and in an inert atmosphere, 13.02 g of HDI biuret (average MM = 549 mol g / mol) was added over 1 hour in the presence of 200 ppm of bismuth carboxylate catalyst. After the addition was complete, the reaction mixture was stirred at 90°C ± 1°C for 60 minutes. As described in Example 1-1, the presence of isocyanate was checked by back titration. If the value was not zero, the reaction was continued for 15 minutes until the reaction was complete.

[0196] When the level reaches zero, the tricarbamate compound Ta4 obtained by formulating the surfactant compound, biocide and defoamer of Example 1-1 is used to obtain a composition consisting of 20% by mass of the compound of the present invention, 5% by mass of the surfactant and 75% by mass of water.

[0197] Examples 1-8: Preparation of compound Ta5 according to the present invention

[0198] In a 3 L glass reactor equipped with a mechanical stirring rod, a vacuum pump and a nitrogen inlet, 301.1 g of a dodecanol / tetradecanol blend ethoxylated with 140 mol of ethylene oxide (MM=6355 Da) and 142.71 g of dodecanol ethoxylated with 30 mol of ethylene oxide (MM=1506 g / mol) were introduced by means of a double jacket heating in which oil was circulated and heated to 90° C. in an inert atmosphere. The blend was dehydrated.

[0199] Then under stirring and in an inert atmosphere, 26.01g HDI isocyanurate (average MM=549 mol / mol) was added in the presence of 200ppm bismuth carboxylate catalyst within 1 hour. After the addition was completed, the reaction mixture was stirred at 90°C ± 1°C for 60 minutes. As described in Example 1-1, the presence of isocyanate was checked by back titration. If the numerical value is not zero, the reaction continues for 15 minutes until the reaction is complete. When the level reaches zero, the tricarbamate compound Ta5 obtained by the surfactant compound, biocide and defoamer formulation of Example 1-1 is used. A composition consisting of 20% by mass of the compound of the present invention, 5% by mass of the surfactant and 75% by mass of water is obtained.

[0200] Example 2: Preparation of a paint formulation according to the invention

[0201] The paint formulations F1 to F6 according to the invention were prepared from aqueous compositions of the triurethane compounds according to the invention. All ingredients used and the proportions (mass %) are listed in Table 1.

[0202] Element Mass (g) water 99.7 Dispersant (Coadis BR3 Coatex) 3.9 Biocide (Acticide MBS Thor) 1.3 Defoaming agent (Airex 901W Evonik) 1.31 <![CDATA[NH4OH(28%)]]> 0.6 <![CDATA[TiO2 pigment (RHD2 Huntsman)]]> 122.2 <![CDATA[CaCO3 pigment (Omyacoat 850 OG Omya)]]> 84.6 Adhesive (Acronal S790 Basf) 270.7 Monopropylene glycol 6.5 Solvent (Texanol Eastman) 6.5 Defoamer (Tego 825 Evonik) 1 Aqueous composition according to the invention 1 28.7 Added water qsp total 650g

[0203] Table 1

[0204] Example 3: Characterization of the paint formulation according to the invention

[0205] For the paint formulations according to the invention, the Brookfield viscosity (μ) measured at 25° C., 10 rpm and 100 rpm was determined 24 hours after preparation using a Brookfield DV-1 viscometer with an RV spindle. Bk10 and μ Bk100 , unit mPa.s).

[0206] The properties of the paint formulations are listed in Table 2.

[0207] preparation Compound <![CDATA[μ Bk10 ]]> <![CDATA[μ Bk100 ]]> F1 Ta1 3620 2108 F2 Tb1 7480 2956 F3 Ta3 2050 1159 F4 Ta5 6820 3456 F5 Tc1 14200 5355 F6 Ta4 15900 8605

[0208] Table 2

[0209] The triurethane compounds according to the present invention are very effective in achieving excellent low shear gradient and medium shear gradient viscosities of paint compositions.

[0210] Example 4: Properties of a paint formulation according to the invention:

[0211] For the paint formulations according to the present invention, the Cone Plan viscosity or ICI viscosity, measured under a high shear gradient (μl, mPa·s), was determined 24 hours after preparation at room temperature using a Cone & Plate Research Equipment London (REL) viscometer with a measuring range of 0 to 5 poise. The viscosity was measured under a moderate shear gradient (μs, Krebs units or KU) using the reference module of a Brookfield KU-2 viscometer. The properties of the paint formulations are listed in Table 3.

[0212] preparation Compound <![CDATA[μ I ]]> <![CDATA[μ S ]]> <![CDATA[μ I / m S ]]> F1 Ta1 350 103 3.4 F2 Tb1 315 109 2.9 F3 Ta3 245 87 2.8 F4 Ta5 280 1 16 2.4

[0213] Table 3

[0214] The tricarbamate compounds according to the invention allow the preparation of paint formulations with particularly controlled viscosities. I The viscosity is very high, so μ I / μ S The compounds according to the invention allow an excellent compromise between high and low shear gradient viscosities.

Claims

1. A tricarbamate compound T selected from: The tricarbamate compound Ta is prepared by reacting the following compounds: 1) one molar equivalent of at least one triisocyanate compound a and 2) one molar equivalent of at least one polyalkoxylated compound b selected from: polyalkoxylated linear aliphatic monoalcohols containing 6 to 40 carbon atoms and containing 2 to 80 alkoxy groups, polyalkoxylated branched aliphatic monoalcohols containing 6 to 40 carbon atoms and 2 to 80 alkoxy groups, polyalkoxylated cycloaliphatic monoalcohols containing 6 to 40 carbon atoms and containing 2 to 80 alkoxy groups, polyalkoxylated monoaromatic monoalcohols containing 6 to 12 or 22 to 30 carbon atoms and containing 2 to 80 alkoxy groups, polyalkoxylated polyaromatic monools containing 10 to 80 carbon atoms and containing 2 to 80 alkoxy groups, 3) two molar equivalents of at least one polyalkoxylated compound c selected from the group consisting of the same or different compounds: polyalkoxylated linear aliphatic monoalcohols containing from 6 to 40 carbon atoms and from 100 to 500 alkoxy groups, polyalkoxylated branched aliphatic monoalcohols containing 6 to 40 carbon atoms and 100 to 500 alkoxy groups, polyalkoxylated cycloaliphatic monoalcohols containing 6 to 40 carbon atoms and 100 to 500 alkoxy groups, polyalkoxylated monoaromatic monoalcohols containing from 6 to 30 carbon atoms and from 100 to 500 alkoxy groups, polyalkoxylated polyaromatic monools containing 10 to 80 carbon atoms and 100 to 500 alkoxy groups; The tricarbamate compound Tb is prepared by reacting the following compounds: 1) one molar equivalent of at least one triisocyanate compound a and 2) one molar equivalent of at least one polyalkoxylated compound b selected from: polyalkoxylated linear aliphatic monoalcohols containing 6 to 40 carbon atoms and containing 2 to 500 alkoxy groups, polyalkoxylated branched aliphatic monoalcohols containing 6 to 40 carbon atoms and 2 to 500 alkoxy groups, polyalkoxylated cycloaliphatic monoalcohols containing 6 to 40 carbon atoms and containing 2 to 500 alkoxy groups, polyalkoxylated monoaromatic monoalcohols containing 6 to 30 carbon atoms and containing 2 to 500 alkoxy groups, polyalkoxylated polyaromatic monools containing 10 to 80 carbon atoms and containing 2 to 500 alkoxy groups, 3) one molar equivalent of at least one polyalkoxylated compound c selected from the group consisting of the same or different compounds: polyalkoxylated linear aliphatic monoalcohols containing 6 to 40 carbon atoms and containing 2 to 500 alkoxy groups, polyalkoxylated branched aliphatic monoalcohols containing 6 to 40 carbon atoms and 2 to 500 alkoxy groups, polyalkoxylated cycloaliphatic monoalcohols containing 6 to 40 carbon atoms and containing 2 to 500 alkoxy groups, polyalkoxylated monoaromatic monoalcohols containing 6 to 30 carbon atoms and containing 2 to 500 alkoxy groups, polyalkoxylated polyaromatic monools containing 10 to 80 carbon atoms and containing 2 to 500 alkoxy groups, 4) one molar equivalent of at least one non-alkoxylated compound c selected from the group consisting of the following identical or different compounds: non-alkoxylated linear aliphatic monoalcohols containing 16 to 40 carbon atoms, Non-alkoxylated branched aliphatic monoalcohols containing 6 to 40 carbon atoms, non-alkoxylated cycloaliphatic monoalcohols containing 6 to 40 carbon atoms, non-alkoxylated monoaromatic monoalcohols containing 6 to 30 carbon atoms, non-alkoxylated polyaromatic monools containing from 10 to 80 carbon atoms; and The tricarbamate compound Tc is prepared by reacting the following compounds: 1) one molar equivalent of at least one triisocyanate compound a and 2) one molar equivalent of at least one polyalkoxylated compound b selected from the group consisting of the same or different compounds: polyalkoxylated linear aliphatic monoalcohols containing 6 to 40 carbon atoms and containing 2 to 500 alkoxy groups, polyalkoxylated branched aliphatic monoalcohols containing 6 to 40 carbon atoms and 2 to 500 alkoxy groups, polyalkoxylated cycloaliphatic monoalcohols containing 6 to 40 carbon atoms and containing 2 to 500 alkoxy groups, polyalkoxylated monoaromatic monoalcohols containing 6 to 30 carbon atoms and containing 2 to 500 alkoxy groups, polyalkoxylated polyaromatic monools containing 10 to 80 carbon atoms and containing 2 to 500 alkoxy groups, 3) two molar equivalents of at least one non-alkoxylated compound c selected from the group consisting of the following identical or different compounds: non-alkoxylated linear aliphatic monoalcohols containing 6 to 40 carbon atoms, Non-alkoxylated branched aliphatic monoalcohols containing 6 to 40 carbon atoms, non-alkoxylated cycloaliphatic monoalcohols containing 6 to 40 carbon atoms, non-alkoxylated monoaromatic monoalcohols containing 6 to 30 carbon atoms, • Non-alkoxylated polyaromatic monools containing from 10 to 80 carbon atoms.

2. The tricarbamate compound T according to claim 1, wherein the reaction uses a single compound a or the reaction uses two or three different compounds a, or Wherein compound a is selected from: ○Triphenylmethane-4,4',4"-triisocyanate or 1,1',1"-methylenetris(4-isocyanatebenzene); o isocyanurate compounds; and ○Biuret trimer compound.

3. The tricarbamate compound T according to any one of claims 1 to 2, wherein compound a is selected from triphenylmethane-4,4',4"-triisocyanate, 1,1',1"-methylenetris(4-isocyanatebenzene), HDI isocyanurate, IPDI isocyanurate, PDI isocyanurate, HDI biuret trimer, IPDI biuret trimer, PDI biuret trimer, and combinations thereof.

4. The tricarbamate compound T according to any one of claims 1 to 2 wherein the degree of polyalkoxylation is from 100 to 500, or wherein the alkoxy group is selected from ethylene oxide (-CH2CH2O-), propylene oxide (-CH2CH(CH3)O- or -CH(CH3)CH2O-), butylene oxide (-CH(CH2CH3)CH2O- or -CH2CH(CH2CH3)O-) and combinations thereof.

5. The tricarbamate compound T according to any one of claims 1 to 2, wherein: The hydrocarbon chain of the polyalkoxylated linear aliphatic monohydric alcohol in compound b contains 6 to 30 carbon atoms, or The hydrocarbon chain of the polyalkoxylated branched aliphatic monohydric alcohol in compound b contains 6 to 30 carbon atoms, or The hydrocarbon chain of the polyalkoxylated alicyclic monool in compound b contains 6 to 30 carbon atoms, or The hydrocarbon chain of the polyalkoxylated polyaromatic monool in compound b contains 10 to 60 carbon atoms.

6. The tricarbamate compound T according to any one of claims 1 to 2, wherein: The hydrocarbon chain of the polyalkoxylated linear aliphatic monohydric alcohol in compound c contains 6 to 30 carbon atoms, or The hydrocarbon chain of the polyalkoxylated branched aliphatic monohydric alcohol in compound c contains 6 to 30 carbon atoms, or The hydrocarbon chain of the polyalkoxylated alicyclic monool in compound c contains 6 to 30 carbon atoms, or The hydrocarbon chain of the polyalkoxylated monoaromatic monool in compound c contains 12 to 30 carbon atoms, or The hydrocarbon chain of the polyalkoxylated polyaromatic monool in compound c contains 10 to 60 carbon atoms, or The hydrocarbon chain of the non-alkoxylated linear aliphatic monohydric alcohol in compound c contains 20 to 30 carbon atoms, or The hydrocarbon chain of the non-alkoxylated branched aliphatic monohydric alcohol in compound c contains 6 to 30 carbon atoms, or The hydrocarbon chain of the non-alkoxylated alicyclic monohydric alcohol in compound c contains 6 to 30 carbon atoms, or The hydrocarbon chain of the non-alkoxylated monoaromatic monool in compound c contains 12 to 30 carbon atoms, or The hydrocarbon chain of the non-alkoxylated polyaromatic monool in compound c contains 10 to 60 carbon atoms.

7. A method for preparing the tricarbamate compound T according to any one of claims 1 to 6 by reacting the following compounds: 1) one molar equivalent of at least one polyisocyanate compound a containing an average of three isocyanate groups and 2) one molar equivalent of at least one polyalkoxylated compound b selected from: polyalkoxylated linear aliphatic monoalcohols containing 6 to 40 carbon atoms, polyalkoxylated branched aliphatic monoalcohols containing 6 to 40 carbon atoms, polyalkoxylated cycloaliphatic monoalcohols containing 6 to 40 carbon atoms, polyalkoxylated monoaromatic monoalcohols containing 6 to 30 carbon atoms, polyalkoxylated polyaromatic monools containing 10 to 80 carbon atoms, 3) two molar equivalents of at least two identical or different compounds c selected from the following: polyalkoxylated linear aliphatic monoalcohols containing 6 to 40 carbon atoms, polyalkoxylated branched aliphatic monoalcohols containing 6 to 40 carbon atoms, polyalkoxylated cycloaliphatic monoalcohols containing 6 to 40 carbon atoms, polyalkoxylated monoaromatic monoalcohols containing 6 to 30 carbon atoms, polyalkoxylated polyaromatic monools containing 10 to 80 carbon atoms, non-alkoxylated linear aliphatic monoalcohols containing 6 to 40 carbon atoms, Non-alkoxylated branched aliphatic monoalcohols containing 6 to 40 carbon atoms, non-alkoxylated cycloaliphatic monoalcohols containing 6 to 40 carbon atoms, non-alkoxylated monoaromatic monoalcohols containing 6 to 30 carbon atoms, • Non-alkoxylated polyaromatic monools containing from 10 to 80 carbon atoms.

8. An aqueous composition comprising: at least one compound selected from the group consisting of the tricarbamate compound T according to any one of claims 1 to 6 and the tricarbamate compound T prepared by the method according to claim 7, and optionally At least one additive selected from: ○Amphiphilic compounds; ○Polysaccharide derivatives; o Solvent; and ○Defoaming agent, biocide.

9. An aqueous formulation comprising: At least one composition according to claim 8; optionally at least one organic or mineral pigment; and optionally • At least one agent selected from the group consisting of particle spacers, dispersants, steric stabilizers, electrostatic stabilizers, opacifiers, solvents, coalescing agents, defoamers, preservatives, biocides, spreading agents, thickeners, film-forming copolymers, and mixtures thereof.

10. The aqueous formulation according to claim 9, wherein the aqueous formulation is a coating formulation.

11. A concentrated water-based pigment slurry comprising at least one tricarbamate compound T according to any one of claims 1 to 6 or at least one tricarbamate compound T prepared by the process according to claim 7, and at least one colored organic pigment or mineral pigment.

12. A method for controlling the viscosity of an aqueous composition, comprising adding at least one tricarbamate compound T according to any one of claims 1 to 6 or at least one tricarbamate compound T prepared by the method according to claim 7.

13. The method according to claim 12, wherein the aqueous composition is a composition according to claim 8 or a formulation as defined in any one of claims 9 and 10.