Rheology control additives containing furan compound

Abstract

The present invention relates to a composition comprising at least one cyclic ether (CE) as component (A) and a urea compound (CU) as component (B), wherein the composition is obtained or obtainable by a process at least comprising the steps of providing a composition (M1) comprising toluene diisocyanate; adding a composition (M2) comprising at least one monohydroxy compound (CM) of formula (I) to obtain a composition (M3) comprising at least one monoisocyanate adduct, wherein in step (ii) the molar ratio of the at least one monohydroxyl compound of general formula (I) to the toluene diisocyanate is in the range of ＞1.0: 1.0 to ≤ 1.5: 1.0; and adding a composition (M4) comprising at least one diamine, at least one cyclic ether to obtain the urea compound (CU). The present invention further relates to a process for preparing a composition according to the present invention and the use of said composition in liquid compositions as a thixotropic agent for paint and coating formulations, adhesive, paint lacquer, PVC plastisol, ink and cement formulations.

Description

[0001] Rheology control additives containing furan compound

[0002] The present invention relates to a composition comprising at least one cyclic ether (CE) as component (A) and a urea compound (CU) as component (B), wherein the composition is obtained or obtainable by a process at least comprising the steps of providing a composition (M1) comprising toluene diisocyanate; adding a composition (M2) comprising at least one monohydroxy compound (CM) of formula (I) to obtain a composition (M3) comprising at least one monoisocyanate adduct, wherein in step (ii) the molar ratio of the at least one monohydroxyl compound of general formula (I) to the toluene diisocyanate is in the range of > 1.0: 1.0 to < 1.5:

[0003] 1.0; and adding a composition (M4) comprising at least one diamine, at least one cyclic ether to obtain the urea compound (CU). The present invention further relates to a process for preparing a composition according to the present invention and the use of said composition in liquid compositions as a thixotropic agent for paint and coating formulations, adhesive, paint lacquer, PVC plastisol, ink and cement formulations.

[0004] It is state of the art to use urea urethane polymers as rheology modifier additives in paints and coating formulations.

[0005] The urea urethane polymer is generally prepared by a two-step procedure wherein in the first step a monohydroxyl compound is reacted in the presence of diisocyanate to synthesize a monoisocyanate adduct; and in the second step the monoisocyanate adduct is reacted with diamine in the presence of a lithium salt and carrier solvent.

[0006] The method of action of the urea-urethanes to modify the rheology in a coating system involves the formation of reversible hydrogen bonds. Once the urea-urethane additive is mixed into the coating, the hydrogen bonds form between the additives and the coating forms a gel. Upon the addition of shear (mixing, shaking, etc.) the hydrogen bonds break up and the coating becomes flowable. After the shear force is removed, the hydrogen bonds build up again and the coating forms a gel again.

[0007] Urea urethane rheology modifier additives are based upon a well-defined stochiochemistry. The isocyanate group can react with any compound containing a reactive hydrogen. Reaction of an isocyanate with an alcohol yields a urethane. The reaction of an isocyanate with an amine yields a urea, and reaction of an isocyanate with water results in intermediates which decompose to yield carbon dioxide and an amine; which further reacts to again form a urea. Other potential isocyanate coreactants include carboxylic acids, urethanes and ureas. In order to prepare polymeric materials, the reaction partners must have at least two functional groups per molecule. The properties of urea urethane polymer depend on certain factors such as degree of branching and position of the functional groups of the reaction partners, content (ratios) of active groups and the physical state of raw materials.

[0008] Different approaches have been suggested in the prior art to obtain the urea urethane polymers.

[0009] US 4,383,068 and US 3,8939,56 describe processes in which polyisocyanate adducts of monoalcohols with diisocyanates and, where appropriate, diisocyanates are reacted with primary and / or secondary polyamines in the mandatory presence of binders to form urea adducts. These urea urethane polymers are prepared in a binder or carrier medium. These binders then have a rheology control property. The rheology control agents cannot be prepared on their own, without these carrier media, and consequently are of only limited usefulness.

[0010] US 4,522,986 describes urethane-urea compounds which are prepared by reacting an NCO- terminated urethane prepolymer with an ethanol amine so as to form hydroxyurea-terminated rheology control agents. These N CO-terminated urethane prepolymers are obtained by reacting a polyether polyol with a stoichiometric excess of an aliphatic, cyclic polyisocyanate. The ure- thane-urea compounds are either isolated by concentration, as wax-like substances, or are isolated by dilution with acetone. The insoluble diurea compounds are isolated as crystalline substances, removed by filtration and discarded. A disadvantage associated with this process is that the stoichiometric excess of the diisocyanate is reacted with the alkanolamine, but must then be removed and discarded, since these ureas are insoluble in polymer solutions and would cause disruptions.

[0011] EP 0 006 252 provides a process for preparing a thixotropic agent and describes urea urethanes that are prepared in aprotic solvents in the presence of lithium chloride by reacting isocyanate adducts with polyamines. The disadvantage of the products prepared in this way is the undefined structure of said urea urethanes due to the preparation process. The preparation process does not provide access to pure monoadducts, but instead forms mixtures of monoadducts and diisocyanates which react with diamines and lead to uncontrolled lengthening of the ureaurethane chain. In the process described, one mol of a diisocyanate is first reacted with one mol of a monoalcohol. This process partly produces the desired NCO-functional monoadducts, but also diadducts without any NCO-functionality. In addition, a proportion of the monomeric diisocyanate remains unreacted. The proportions of these different compounds may vary, depending on the accessibility of the NCO group and the reaction conditions applied, such as temperature and time. All these adducts prepared in this way contain fairly large amounts of unreacted diiso- cyanate that, during the further reaction with polyamines in the presence of lithium chloride, results in uncontrolled chain extension of the urea urethane and in polymeric ureas. These products then have a tendency to precipitation and can be kept in solution only with the greatest difficulty.

[0012] US 6,420,466 describes a process for preparing a thixotropic agent which contains urea-ure- thanes wherein monohydroxyl compounds are reacted with an excess of toluene diisocyanate, whereby the unreacted portion of the toulene is removed from the reaction mixture and the monoisocyanate adduct obtained is further reacted with diarines in the presence of Lithium salts. The disadvantage of this process is that the subsequent removal of the stoichiometric excess of diisocyanate by vacuum distillation is a complex and expensive process. Also, because of the diurea-urethanes that are deliberately prepared, only a few active urea groups can be incorporated into the molecule and, consequently, the efficiency of these urea-urethanes is limited.

[0013] W02020 / 182944 discloses a composition comprising one or more urea-based compounds having a number average molecular weight (Mn) between 350 g / mol and 30000 g / mol and one or more N-substituted caprolactam derivatives.

[0014] Despite the fact that urea urethane polymers are being commercially prepared and used for many years, there is still an ongoing need to provide a process for preparing urea urethane polymers which does not require a diisocyanate distillation step. It has been a challenge for the researchers to reduce the free diisocyanate in the first step such that the monoisocyanate adduct, i.e. without free diisocyanates, is formed which when reacts with the diamine in the second step results into a more definite structure of urea urethane polymer.

[0015] WO2022 / 043175 and W02019 / 096611 also disclose polyurea rheology modifiers which are prepared using a process without distillation step.

[0016] It was an object of the present invention to provide a process for preparing storage stable urea urethane polymers which can be prepared in a simple and economical process, avoiding the disadvantages associated with the presence of free diisocyanate and providing a urea urethane polymer which upon use in paint and coating formulations imparts thickening effect and thixotropic properties to the formulations.

[0017] According to the present invention, this object has been solved by a composition comprising (a) at least one cyclic ether (CE) with a molecular weight in the range of from 80 to 500 g / mol as component (A) in an amount in the range of from 10 to 80 wt% based on the weight of the composition and

[0018] (b) a urea compound (CU) as component (B) in an amount in the range of from 10 to 80 wt% based on the weight of the composition, wherein the sum of the components of the composition adds up to 100 wt%, wherein the composition is obtained or obtainable by a process at least comprising the steps

[0019] (i) providing a composition (M1) comprising toluene diisocyanate;

[0020] (ii) adding a composition (M2) comprising at least one monohydroxy compound (CM) of formula (I) to obtain a composition (M3) comprising at least one monoisocyanate adduct, wherein in step (ii) the molar ratio of the at least one monohydroxyl compound of general formula (I) to the toluene diisocyanate is in the range of > 1.0: 1.0 to < 1.5: 1.0;

[0021] (iii) adding a composition (M4) comprising at least one diamine, at least one cyclic ether to obtain the urea compound (CU); wherein the monohydroxy compound (CM) has the general formula (I)

[0022] R1-OH (I), wherein

[0023] R1is selected from linear or branched, substituted or unsubstituted C4-C22 alkyl, linear or branched, substituted or unsubstituted C4-C22 alkenyl, substituted or unsubstituted C6-C12 cycloalkyl, linear or branched, substituted or unsubstituted C7-C24 aralkyl, and substituted or unsubstituted Ce-C24 aryl, a radical of formula R11(O-CnH2n)x-, a radical of formula R11[O-C(=O)-CvH2v]x-, and a radical of formula R11(O-CnH2n)x-i [O-C(=O)-CvH2v]x-, wherein

[0024] R11is selected from linear or branched, substituted or unsubstituted C4-C22 alkyl, linear or branched, substituted or unsubstituted C4-C22 alkenyl, substituted or unsubstituted C6-C12 cycloalkyl, linear or branched, substituted or unsubstituted C7-C24 aralkyl, and substituted or unsubstituted Ce-C24 aryl, n is an integer from 2 to 4, x is an integer from 1 to 15, and v is an integer from 4 to 6.

[0025] According to the present invention, the composition is obtained by a process comprising steps (i), (ii), and (iii). The process might also comprise further steps.

[0026] According to step (i), a composition (M1) comprising toluene diisocyanate is provided. Composition (M1) comprises the toluene diisocyanate and may comprise further components such as for example solvents.

[0027] In the context of the present invention, further solvents may be used. According to the invention, the solvent used in the process does not comprise further cyclic ethers. In particular, polar aprotic solvents may be used.

[0028] According to step (ii), a composition (M2) comprising at least one monohydroxy compound (CM) of formula (I) is added to obtain a composition (M3) comprising at least one monoisocyanate adduct, wherein in step (ii) the molar ratio of the at least one monohydroxyl compound of general formula (I) to the toluene diisocyanate is in the range of > 1.0: 1.0 to < 1.5: 1.0. Composition (M2) comprises the monohydroxy compound (CM) and may also comprise further components.

[0029] According to step (iii), composition (M4) comprising at least one diamine, at least one cyclic ether (CE) is added to obtain the urea compound (CU). Composition (M4) comprises at least one diamine and at least one cyclic ether but may also comprise further components.

[0030] The composition comprises the cyclic ether (CE) as component (A) in an amount in the range of from 10 to 80 wt% based on the weight of the composition, wherein the sum of the components of the composition adds up to 100 wt%. Furthermore, the composition comprises the urea compound (CU) as component (B) in an amount in the range of from 10 to 80 wt% based on the weight of the composition, wherein the sum of the components of the composition adds up to 100 wt%. The composition preferably comprises a salt compound as component (C) in an amount in the range of from 0 to 25 wt% based on the weight of the composition, wherein the sum of the components of the composition adds up to 100 wt%. The composition preferably comprises an organic solvent as component (D) in an amount in the range of from 0 to 50 wt%, more preferable in the range of from 10 to 50 wt% based on the weight of the composition, wherein the sum of the components of the composition adds up to 100 wt%. Therefore, according to a further embodiment, the present invention is also directed to the composition as disclosed above, wherein the composition comprises

[0031] (a) the cyclic ether (CE) as component (A) in an amount in the range of from 10 to 80 wt% based on the weight of the composition,

[0032] (b) the urea compound (CU) as component (B) in an amount in the range of from 10 to 80 wt% based on the weight of the composition,

[0033] (c) a salt compound as component (C) in an amount in the range of from 0 to 25 wt% based on the weight of the composition,

[0034] (d) an organic solvent as component (D) in an amount in the range of from 10 to 50 wt% based on the weight of the composition, wherein the sum of the components of the composition adds up to 100 wt%.

[0035] The composition according to the present invention comprises at least one cyclic ether (CE) as component (A) and a urea compound (CU) as component (B).

[0036] Surprisingly, it has been found that the presence of the cyclic ether (CE) and using an excess of monohydroxyl compound represented by general formula R-OH to diisocyanate, i.e. the molar ratio of the monohydroxyl compound to the toluene diisocyanate being in the range of > 1 .0: 1 to < 1.5: 1 , leads to the formation of a urea urethane polymer with advantageous properties. According to the present invention, the presence of the cyclic ether (CE) results in good thickening properties and a good eco-environment friendly composition.

[0037] It has been surprisingly found that in the process of preparing a urea urethane polymer, the monoisocyanate adduct obtained by reacting a monohydroxyl compound represented by R-OH and toluene diisocyanate in a molar ratio in the range of > 1 .0: 1 .0 to < 1 .5: 1 .0, when reacted with diamine in the presence of a polar aprotic solvent and lithium salt, provides a urea urethane polymer, without the step of distillation of the diisocyanate. The process provides a urea urethane polymer which is stable and which upon use as an additive in paint and coating formulations imparts thixotropic properties to the formulations. The urea urethane polymer according to the present invention is used as a thixotropic agent for paint and coating formulations, lacquer, varnish, paper coating, wood coating, adhesive, ink, cosmetic formulation, detergent formulation, textile and drilling muds plaster formulations, PVC plastisol and cement formulations.

[0038] The present invention is directed to a process for preparing a urea urethane polymer which is used as an additive in solvent-containing, solvent free and water based paint and coating formulations, for imparting the thixotropic properties to said formulations thereby enabling the use of urea urethane polymer obtained by the process of the present invention to modify the rheological profile of paint and coating formulations, lacquer, varnish, paper coating, wood coating, adhesive, ink, cosmetic formulations, detergent formulations, textile and drilling muds plaster formulations, PVC plastisol and cement formulations.

[0039] The term “thixotropic effect” as used herein means a property exhibited by a viscous or a gel like product turning more liquid as it is deformed for longer time and more rigorously (e.g. by stirring).

[0040] The term "alkyl", as used herein, refers to an acylic saturated aliphatic groups that is solely constituted of carbon atoms and hydrogen atoms, including linear or branched alkyl residues. Furthermore, the alkyl residue is preferably unsubstituted.

[0041] The term "alkenyl", as used herein, refers to acyclic unsaturated hydrocarbon residues, including linear or branched alkenyl residues, and comprise at least one double bond, preferably 1, 2, or 3 double bonds. Furthermore, the alkenyl residue is preferably unsubstituted. Representative examples of alkenyl include, but are not limited to, 1-hexenyl,2-hexenyl, 1-heptenyl, 2-heptenyl, 1 -octenyl, 2-octenyl, 1-nonenyl, 2-nonenyl, 1-decenyl, 2-decenyl, 1-undecenyl, 2- undecenyl, 1 -dodecenyl, 2-dodecenyl, 1 -tridecenyl, 2- tridecenyl, 1 -tetradecenyl, 2-tetrade- cenyl, 1-pentadecenyl,2-pentadecenyl, 1-hexadecenyl,2-hexadecenyl, 1 -heptadecenyl, 2- heptadecenyl, 1 -octadecenyl, 2-octadecenyl, 1-nonadecenyl, 2-nonadecenyl, 1-eicosenyl and 2-eicosenyl.

[0042] Within the context of the present invention and as used herein, the term “cycloalkyl” refers to a saturated cyclic hydrocarbon residue including 6, 7, 8, 9, 10, 11 or 12 atoms, as ring members. The cycloalkyl group is preferably unsubstituted.

[0043] As used herein, “branched” denotes a chain of atoms with one or more side chains attached to it. Branching occurs by the replacement of a substituent, e.g., a hydrogen atom, with a covalently bonded aliphatic moiety.

[0044] The term “aralkyl” refers to a radical derived from an alkyl radical by replacing one or more hydrogen atoms by an aryl group. Furthermore, the aralkyl residue is preferably unsubstituted. Representative examples of aralkyl include, but are not limited to, benzyl, o-tolyl, m-tolyl, p-tolyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5-xylyl and mesityl. The term “aryl” refers to aromatic carbocyclic rings of 6 to 30 ring members, including both mono, bi-, and tri-cyclic ring systems. Non-limiting examples of aryl include indenyl, phenyl and naphthyl.

[0045] In context of the present invention the term “monoisocyanate adduct” refers to an addition product of monohydroxyl compound of general formula (I) and toluene diisocyanate. The monoisocyanate adduct has free reactive isocyanate groups which react with diamine.

[0046] The term “polar aprotic solvent” refers to a solvent made of polar molecules with a comparatively high relative permittivity (or dielectric constant), greater than 15, and a permanent dipole moment, that cannot donate suitably labile hydrogen atoms to form strong hydrogen bonds.

[0047] The term “theoretical NCO content” refers to the content of NCO which is theoretically calculated based on only half amount of the NCO groups from TDI raw material reacted with R-OH.

[0048] Suitable cyclic ethers which may be used according to the present invention might be monocyclic, bicyclic or polycyclic ethers. It is also possible to use monocyclic compounds with two or more ether groups. Suitable ethers have a molecular weight in the range of from 80 to 500 g / mol, more preferable in the range of from 80 to 250 g / mol. Preferably, bicyclic ethers having a molecular weight in the range of from 80 to 250 g / mol are used.

[0049] Therefore, according to a further embodiment, the present invention is also directed to the composition as disclosed above, wherein the cyclic ether is a bicyclic ether having a molecular weight in the range of from 80 to 250 g / mol.

[0050] It has been found that dimethyl isosorbide (DMI) and dihydrolevoglucosenone (DHGS) are particularly suitable. Therefore, according to a further embodiment, the present invention is also directed to the composition as disclosed above, wherein the cyclic ether is selected from the group consisting of dimethyl isosorbide (DMI) and dihydrolevoglucosenone (DHGS).

[0051] Preferably, the toluene diisocyanate is selected from either 2,4-toluene diisocyanate or an isomeric mixture of 2,4-toluene diisocyanate and 2,6-toluene diisocyanate, preferably an isomeric mixture of 2,4-toluene diisocyanate and 2,6-toluene diisocyanate.

[0052] Therefore, according to a further embodiment, the present invention is also directed to the composition as disclosed above, wherein the toluene diisocyanate is selected from 2, 4-toluene diisocyanate and a mixture of 2, 4-toluene diisocyanate and 2, 6-toluene diisocyanate. In an embodiment according to the present invention, the 2,4- toluene diisocyanate is present in the isomeric mixture in an amount in the range of > 85.0 wt.-% to < 99.9 wt.-%, related to the total weight of the isomeric mixture, preferably in the range of > 90.0 wt.-% to < 99.9 wt.-% of the 2,4-isomer, and most preferably in the range of > 95.0 wt.-% to < 99.9 wt.-% of the 2,4-iso- mer .

[0053] In an embodiment according to the present invention, the molar ratio of the at least one monohydroxyl compound of general formula (I) to the toluene diisocyanate is in the range of > 1 .0: 1 .0 to < 1.5: 1 .0, preferably in the range of > 1 .005: 1 .0 to < 1.45: 1 .0, more preferably in the range of > 1.01 : 1.0 to < 1.4: 1.0, even more preferably in the range of > 1.025: 1.0 to < 1 .35: 1 .0, further more preferably in the range of > 1.050: 1.0 to < 1 .3: 1 .0 or in the range of > 1.075: 1 .0 to < 1.25: 1 .0, most preferably in the range of > 1 .1 : 1 .0 to < 1.2: 1 .0 or > 1 .005: 1 .0 to < 1.2: 1.0.

[0054] Preferably, in the monohydroxyl compound of general formula (I), R is a linear or a branched alkyl selected from the group consisting of n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n- decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n- octadecyl, n-nonadecyl, n-eicosyl, n-heneicosyl, n-docosyl, 2-ethylhexyl, 2-propyl-heptyl, 2-bu- tyl-1-octyl, 2-pentyl-1 -nonyl, isobutyl, isopentyl, isohexyl, isoheptyl, isooctyl, isodecyl, isoundecyl, isododecyl, isotridecyl, isotetradecyl, isopentadecyl, isohexadecyl, isoheptadecyl, isooctadecyl, isononadecyl, isoeicosyl, isoheneicosyl, and isodocosyl.

[0055] In an embodiment according to the present invention, in the monohydroxyl compound of general formula (I), R is a linear or a branched alkenyl selected from the group consisting 1-hexenyl,2- hexenyl, 1-heptenyl, 2-heptenyl, 1 -octenyl, 2-octenyl, 1-nonenyl, 2-nonenyl, 1-decenyl, 2-de- cenyl, 1-undecenyl, 2-undecenyl, 1-dodecenyl, 2-dodecenyl, 1 -tridecenyl, 2- tridecenyl, 1- tetradecenyl, 2-tetradecenyl, 1 -pentadecenyl, 2-pentadecenyl, 1- hexadecenyl, 2- hexadecenyl, 1-heptadecenyl,2-heptadecenyl, 1 -octadecenyl, 2-octadecenyl, 1-nonadecenyl, 2-non- adecenyl, 1-eicosenyl, 2-eicosenyl, cis-7-decenyl, cis-9-octadecenyl (oleyl), cis-8,11-heptade- cadienyl, cis-9,12-octadecadienyl (linoleyl), cis-10,13-nonadecadienyl and cis-6,9,12-octadeca- trienyl.

[0056] In an embodiment according to the present invention, in the monohydroxyl compound of general formula (I), R is a cycloalkyl selected from the group consisting of cyclohexyl, cycloheptyl, cy- cloctyl, cyclononyl, cyclodecyl, cycloundecyl, and cyclododecyl. In an embodiment according to the present invention, in the monohydroxyl compound of general formula (I), R is an aralkyl selected from the group consisting of benzyl, o-tolyl, m-tolyl, p-tolyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5-xylyl and mesityl.

[0057] In an embodiment according to the present invention, in the monohydroxyl compound of general formula (I), R is a radical of formula CmH2m+i (O-CnH2n)x-, wherein m is an integer from 1 to 22, n is an integer from 2 to 4, x is an integer from 1 to 15.

[0058] In an embodiment according to the present invention, in the monohydroxyl compound of general formula (I), R is a radical of formula H(O-CnH2n)x-, wherein m is an integer from 1 to 22, n is an integer from 2 to 4, x is an integer from 1 to 15.

[0059] In an embodiment according to the present invention, in the monohydroxyl compound of general formula (I), R is a radical of formula CmH2m+i [O-C(=O)-CvH2v]x-, wherein m is an integer from 1 to 22, n is an integer from 2 to 4, x is an integer from 1 to 15 and v is an integer from 4 to 6.

[0060] In an embodiment according to the present invention, in the monohydroxyl compound of general formula (I), R is a radical of formula CmH2m+i (O-CnH2n)x-i [O-C(=O)-CvH2v]x-, wherein m is an integer from 1 to 22, n is an integer from 2 to 4, x is an integer from 1 to 15 and v is an integer from 4 to 6.

[0061] In an embodiment according to the present invention, in general formula (I) m is an integer from 1 to 4.

[0062] In an embodiment according to the present invention, in general formula (I) n is 2.

[0063] In an embodiment according to the present invention, in general formula (I) x is an integer from 3 to 10.

[0064] According to a further embodiment, the present invention is also directed to the composition as disclosed above, wherein the at least one monohydroxy compound of formula (I) is selected from butyltriglycol, butyldiglycol, butyltetraglycol, butanol, isotridecyl alcohol, oleyl alcohol, Guer- bet alcohols containing 8 to 20 carbon atoms, linoleyl alcohol, lauryl alcohol, stearyl alcohol, cyclohexanol, benzyl alcohol, 4-dodecylphenol, ethoxylated triphenylmethanol and ethoxylated 4- dodecylphenol. According to the present invention, the at least one monohydroxyl compound of general formula (I) preferably is selected from the group consisting of butyltriglycol, methoxy polyethylene glycol, butanol, isotridecyl alcohol, oleyl alcohol, Guerbet alcohols containing 8 to 20 carbon atoms, linoleyl alcohol, lauryl alcohol, stearyl alcohol, cyclohexanol and benzyl alcohol, preferably from the group consisting of butyltriglycol, 2-ethylhexanol and methoxy polyethylene glycol.

[0065] Guerbet alcohols are represented by the general formula (X),

[0066] (X), wherein p is 1, 2, 3 or 4.

[0067] The trivial name of Guerbet alcohol is used for 2-alkyl-substituted 1 -alkanols whose industrial synthesis is described inter alia in H. Machemer, Angewandte Chemie, Vol. 64, pages 213-220 (1952) and in G. Dieckelmann and H.J. Heinz in "The Basics of Industrial Oleochemistry", pages 145-145 (1988).

[0068] In an embodiment the Guerbet alcohol is selected from 2-ethylhexanol, 2-propyl-heptanol, 2-bu- tyl-1 -octanol and 2-pentyl-1 -nonanol.

[0069] In an embodiment according to the present invention, the at least one monohydroxyl compound of general formula (I) in step (ii) is added during a time period in the range of > 3 hours to < 50 hours, preferably in the range of > 3 hours to < 30 hours, and more preferably in the range of > 3 hours to < 20 hours.

[0070] In an embodiment according to the present invention, in step ii) the temperature is in the range of > 20°C to < 60°C, preferably in the range of > 25°C to < 55°C, and more preferably in the range of > 30°C to < 50°C.

[0071] In an embodiment according to the present invention, in step (ii) optionally a solvent (D) is added wherein the solvent used in the process does not comprise further cyclic ethers. The solvent used should be essentially inert to the reaction. While it may not be necessary to employ the solvent during formation of the urethane prepolymer, the use of a solvent may be desirable to maintain the reactants in the liquid state as well as permit better temperature control during the reaction by serving as a heat sink and, if desired, as a refluxing medium. In any event, the pre-polymer is in solution during its reaction with diamine to form the urea-urethane. Exemplary of other solvents which do not contain reactive hydrogen are esters, ethers, ketoesters, ketones, glycol-ether-esters, chlorinated hydrocarbons, aliphatic and alicyclic hydrocarbons, pyrrolidones, hydrogenated furans, and the like and mixtures thereof. According to the present invention, solvent (D) is different from the cyclic ether (CE).

[0072] In a preferred embodiment according to the present invention, the optional solvent is selected from the group consisting of acetone, benzene, ethyl acetate, butyl acetate, diethylether, carbon tetrachloride and chlorobenzene.

[0073] Suitable diamines which may be used according to the present invention are in principle known. Therefore, according to a further embodiment, the present invention is also directed to the composition as disclosed above, wherein the at least one diamine is selected from diamines of formula (Ila), (lib), (He), (lid) and (He);

[0074] H2N-R3-NH2(Ha), wherein R3is -CyH2y- and y is an integer from 2 to 12, diamine of formula (Hb) diamines of formula (Hd) wherein, in formula (He), formula (Hd) and formula (lie), R4are identical or different and are selected from H, CH3-, C2H5- and C3H7-, and R5is selected from -CH2- , -C2H4-, -C3H6- and -C6H12-.

[0075] Preferably, the at least one diamine is selected from the group consisting of 4,4-diamino-diphe- nylmethane, 3,3- dimethyl-4,4-diamino-diphenylmethane, 2,2-bis(4-aminocyclohexyl)-propane, N,N-dimethyl-4,4-diaminodiphenylmethane,(3-methyl-4-aminocylcohexyl)-(3-methyl-4-amino- phenyl)-methane, 4, 4 diaminodicyclohexylmethane, isomeric xylylenediamine, ethylenediamine, hexamethylenediamine, 4,4-methylenebis(cyclohexylamine), 1 ,12-diaminododecane, neo- pentanedimaine, 1 ,2- and 1 ,3- propanediamine, 1 , 8- octamethylenediamine and 1 , 12-dodeca- methylenediamine.

[0076] Typically, the urea compound (CU) has a weight average molecular weight in the range of > 300 g / mol to < 5000 g / mol, determined according to DIN 55672-2.

[0077] Preferably, the urea urethane obtained has a weight average molecular weight in the range of > 500 g / mol to < 3000 g / mol determined according to DIN 55672-1 , preferably in the range of > 700 g / mol to < 3000 g / mol, more preferably in the range of > 1000 g / mol to < 2500 g / mol, and even more preferably in the range of > 1500 g / mol to < 2500 g / mol.

[0078] Therefore, according to a further embodiment, the present invention is also directed to the composition as disclosed above, wherein the urea compound (CU) has a weight average molecular weight in the range of > 300 g / mol to < 5000 g / mol, determined according to DIN 55672-2. Preferably, the at least one solvent (D) is a polar aprotic solvent, in particular a polar aprotic solvent selected from the group consisting of dimethyl sulfoxide, N, N- dimethylformamide, N, N- dimethylacetamide, N-methylpyrrolidone, N-ethylpyrrolidone, N-propylpyrrolidone, N-butylpyrrol- idone, or comparable alkyl pyrrolidone or mixtures thereof, N,N,N',N'-tetramethylurea, acetonitrile, acetone and hexamethyl- phosphoric acid triamide.

[0079] Therefore, according to a further embodiment, the present invention is also directed to the composition as disclosed above, wherein the at least one polar aprotic solvent is selected from the group consisting of dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N- methylpyrrolidone, N-ethylpyrrolidone, N-propylpyrrolidone, N-butylpyrrolidone, N,N,N',N'-tetra- methylurea, hexamethyl- phosphoric acid triamide and methyl 5-(dimethylamino)-2-methyl-5- oxopentanoate.

[0080] In an embodiment according to the present invention, the weight ratio of toluene diisocyanate to the optional solvent is in the range of > 0.5: 1.0 to < 5.0: 1 .0, preferably in the range of > 1.0: 1 .0 to < 4.5: 1.0, more preferably in the range of > 1.5: 1.0 to < 4.0: 1.0, more preferably in the range of > 2.0: 1.0 to < 3.5: 1.0, and most preferably in the range of > 2.5: 1.0 to < 3.0: 1 .0.

[0081] According to a further embodiment, the present invention is also directed to the composition as disclosed above, wherein the salt is a metal salt selected from the group consisting of lithium chloride, lithium nitrate, lithium bromide, and dioctyl sulfosuccinate sodium salt.

[0082] More preferable, the lithium salt is selected from the group consisting of lithium chloride, lithium nitrate and lithium bromide.

[0083] In an embodiment according to the present invention, the lithium salt is present in the range of > 0.3 to < 1.5 mol, relative to the equivalent weight of the at least one diamine, preferably in the range of > 0.5 to 1 .0 < mol.

[0084] The conditions applied in steps (i) to (iii) of the process according to the present invention might vary in broad ranges. Preferably, in step (iii) the temperature is in the range of > 30°C to < 100°C, preferably in the range of > 40°C to < 80°C, and more preferably in the range of > 40°C to < 60°C.

[0085] Preferably, any solvent added in step (i) or (ii) is removed at the end of step (iii). In an embodiment according to the present invention, in step (ii), the NCO content via titration is lower than 110%, preferably lower than 105%, of the “theoretical NCO content”. The “theoretical NCO content” here is theoretically calculated based on only half amount of the NCO groups from TDI raw material reacted with R-OH. In an embodiment according to the present invention, in step (iii), the NCO content is preferably 0%.

[0086] According to a further aspect, the present invention is also directed to a process for preparing a composition as disclosed above comprising the steps:

[0087] (i) providing a composition (M1) comprising toluene diisocyanate;

[0088] (ii) adding a composition (M2) comprising at least one monohydroxy compound (CM) of formula (I) to obtain a composition (M3) comprising at least one monoisocyanate adduct, wherein in step (ii) the molar ratio of the at least one monohydroxyl compound of general formula (I) to the toluene diisocyanate is in the range of > 1 .0: 1 .0 to < 1.5: 1.0;

[0089] (iii) adding a composition (M4) comprising at least one diamine and at least one cyclic ether (CE) to obtain the urea compound (CU); wherein the monohydroxy compound (CM) has the general formula (I)

[0090] R1-OH (I), wherein R1is selected from linear or branched, substituted or unsubstituted C4-C22 alkyl, linear or branched, substituted or unsubstituted C4-C22 alkenyl, substituted or unsubstituted C6-C12 cycloalkyl, linear or branched, substituted or unsubstituted C7-C24 aralkyl, and substituted or unsubstituted Ce-C24 aryl, a radical of formula R11(O-CnH2n)x-, a radical of formula R11[O-C(=O)-CvH2v]x-, and a radical of formula R11(O-CnH2n)x-i [O-C(=O)-CvH2v]x-, wherein

[0091] R11is selected from linear or branched, substituted or unsubstituted C4-C22 alkyl, linear or branched, substituted or unsubstituted C4-C22 alkenyl, substituted or unsubstituted C6-C12 cycloalkyl, linear or branched, substituted or unsubstituted C7-C24 aralkyl, and substituted or unsubstituted Ce-C24 aryl, n is an integer from 2 to 4, x is an integer from 1 to 15, and v is an integer from 4 to 6.

[0092] With respect to preferred embodiments, reference is made to the disclosure above.

[0093] Furthermore, the present invention provides a liquid composition comprising > 0.01 wt.-% to < 10.0 wt.-%, based on the total weight of the liquid composition, of the urea urethane obtained according to the process of the present invention, preferably in the range from > 0. 1 wt.-% to 7.0 < wt.-%, more preferably in the range from > 0.1 wt.-% to < 5.0 wt.-%, even more preferably in the range from > 0.1 wt.-% to < 3.0 wt.-%; and > 15.0 wt.-% to 99.9 < wt.-%, preferably > 25.0 wt.-% to 90.0 < wt.-%, more preferably > 35.0 wt.-% to 85.0 < wt.-%, even more preferably > 50.0 wt.-% to < 80.0 wt.-%, and most preferably > 55.0 wt.-% to < 75.0 wt.-% based on the total weight of the liquid composition of at least one of the components, selected from the group consisting of pigment pastes, binders, fillers, solvents, defoamers, neutralising agent, wetting agent, pigment dispersing agents, preservatives and water.

[0094] Therefore, according to a further aspect, the present invention is also directed to a liquid composition comprising > 0.01 wt.-% to < 10.0 wt.-%, based on the total weight of the liquid composition, of the composition according to any one of claims 1 to 10; and > 15.0 wt.-% to 99.9 < wt.- %, based on the total weight of the liquid composition of at least one of the components, selected from the group consisting of pigment pastes, binders, fillers, solvents, defoamers, neutralising agent, wetting agent, pigment dispersing agents, preservatives and water.

[0095] Preferably, the composition is a water based or a solvent based paint and coating formulations, lacquer, varnish, paper coating, wood coating, adhesive, ink, cosmetic formulation, detergent formulation, textile and drilling muds plaster formulations, cement compositions, formulations for plasterboard, for hydraulic binders such as mortar formulations, formulations for ceramics and for leather, preferably water based and solvent based paint and coating formulations, adhesives, inks and cementitious formulations.

[0096] In an embodiment the present invention provides a use of the urea urethane obtained according to the process of the present invention in liquid compositions as a thixotropic agent for paint and coating formulations, adhesive, paint lacquer, PVC plastisol, ink and cement formulations, preferably for water based and solvent based paint and coating formulations, adhesives, inks and cementitious formulations. In a preferred embodiment the liquid composition is a water based or solvent based paint and coating formulation. Paints and coating compositions for the purposes of the invention are those, which are applied from liquid phase to a substrate and, with the formation of a film, form a protective or functional and / or decorative surface. By substrates are meant, for example, wood, metals, polymeric films, polymeric parts, paper, leather, fingernails and toenails, and construction materials, such as masonry, concrete and plasters, for example. The coating materials in question may be unpigmented, pigmented or dye-containing coating materials, which may in turn contain different kinds of binders, alone or in a mixture, along with other additives such as filler, binders, neutralizing agents, pigments, defoamers, wetting agents, pigment dispersing agents etc. A few examples of the additives used in the coating formulations are:

[0097] According to a further embodiment, the present invention is also directed to a liquid composition as disclosed above, wherein the composition is a paint, water based coating formulations, solvent based coating formulations, lacquer, varnish, paper coating, wood coating, adhesive, ink, cosmetic formulation, detergent formulation, textile, and drilling muds plaster formulations, cement compositions, formulations for plasterboard, for hydraulic binders such as mortar formulations, formulations for ceramics and for leather.

[0098] Suitable fillers are, for example, organic or inorganic particulate materials such as, for example, calcium carbonates and silicates, and also inorganic fiber materials such as glass fibers, for example. Organic fillers as well, such as carbon fibers, and mixtures of organic and inorganic fillers, such as mixtures of glass fibers and carbon fibers or mixtures of carbon fibers and inorganic fillers, for example, may find application.

[0099] Suitable binders are the ones customarily used, for example the ones described in 30 Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, Vol. A18, pp. 368-426, VCH, Weinheim 1991 , Germany. In general, the film-forming binder is based on a thermoplastic or thermosetting resin. Examples thereof are alkyd, acrylic, unsaturated or saturated polyester resin, acrylate and methacrylate resins, nitrocellulose, cellulose acetobutyrate, alkyd-amino resins, alkyd resins, melamine resins, urea resins, silicone resins, phenolic, melamine, epoxy and polyurethane resins and mixtures thereof. Also resins curable by radiation or air-drying 35 resins can be used. Binders may also be derived from polyvinylalcohol and polyvinylbutyral. Binders include latex polymers made by emulsion polymerization. For architectural coatings especially preferred latex polymers are based on acrylic emulsion polymers, styrene-acrylic emulsion polymers, vinyl ace- tate-acrylic emulsion polymers or emulsion polymers based on ethylene and vinyl acetate. Organic or inorganic pigments are suitable as additives. Examples of organic pigments are color pigments and mother-of-pearl-like pigments such as azo, disazo, naphthol, benzimidazolone, azo condensation, metal complex, isoindolinone, quinophthalone, and dioxazine pigments, polycyclic pigments such as indigo, thioindigo, quinacridones, phthalocyanines, perylenes, peri- nones, anthraquinones, e.g., aminoanthraquinones or hydroxyanthraquinones, anthrapyrim- idines, indanthrones, flavanthrones, pyranthrones, anthanthrones, isoviolanthrones, diketo- pyrrolopyrroles, and also carbazoles, e.g., carbazole violet, and the like. Other examples of organic pigments can be found in the following monograph: W. Herbst, K. Hunger, “Industrielle Organische Pigmente”, 2nd edition, 1995, VCH Verlagsgesellschaft, ISBN: 3 527 28744 2. Examples of inorganic pigments are titanium dioxide, metallic flakes, such as aluminum and also aluminum oxide, iron (III) oxide, chromium (III) oxide, titanium (IV) oxide, zirconium(IV)oxide, zinc oxide, zinc sulfide, zinc phosphate, mixed metal oxide phosphates, molybdenum sulfide, cadmium sulfide, graphite, vanadates such as bismuth vanadate, chromates, such as lead(IV) chromates, molybdates such as lead(IV) molybdate, and mixtures thereof.

[0100] Suitable neutralizing agents are inorganic bases, organic bases, and combinations thereof. Examples of inorganic bases include but are not limited to the alkali metal hydroxides (especially lithium, sodium, potassium, magnesium, and ammonium), and alkali metal salts of inorganic acids, such as sodium borate (borax), sodium phosphate, sodium pyrophosphate, and the like; and mixtures thereof. Examples of organic bases include but are not limited to triethanolamine (TEA), diisopropanolamine, triisopropanolamine, aminomethyl propanol (2-Amino-2-methyl-1 - propanol), dodecylamine, cocamine, oleamine, morpholine, triamylamine, triethylamine, tetrakis(hydroxypropyl)ethylenediamine, L-arginine, methyl glucamine, isopropylamine, aminomethyl propanol, tromethamine (2-amino 2-hydroxymethyl-1 ,3-propanediol), and PEG-15 cocamine. Alternatively, other alkaline materials can be used alone or in combination with the above-mentioned inorganic and organic bases.

[0101] Suitable defoamers are selected from the wide range of defoamer used such as silicone based defoamers, emulsion defoamers, star polymer based defoamers, powder defoamers, oil based defoamers.

[0102] The process of the present invention is a simple and economical process as no diisocyanate distillation step is required.

[0103] The process provides a stable urea urethane polymer which upon use as an additive in paint and coating formulations imparts thixotropic effects to said formulations. The present invention is also directed to the use of the composition as disclosed above or the composition obtained or obtainable according to the process as disclosed above in liquid compositions as a thixotropic agent for paint and coating formulations, adhesive, paint lacquer, PVC plastisol, ink and cement formulations.

[0104] Further embodiments of the present invention can be found in the claims and the examples. It will be appreciated that the features of the subject matter / processes / uses according to the invention that are mentioned above and elucidated below are usable not only in the combination specified in each case but also in other combinations without departing from the scope of the invention. For example, the combination of a preferred feature with a particularly preferred feature or of a feature not characterized further with a particularly preferred feature etc. is thus also encompassed implicitly even if this combination is not mentioned explicitly.

[0105] The present invention is further illustrated by the following set of embodiments and combinations of embodiments resulting from the dependencies and back-references as indicated. In particular, it is noted that in each instance where a range of embodiments is mentioned, for example in the context of a term such as "The composition of any one of embodiments 1 to 4", every embodiment in this range is meant to be explicitly disclosed for the skilled person, i.e. the wording of this term is to be understood by the skilled person as being synonymous to "The composition of any one of embodiments 1 , 2, 3 and 4". Further, it is explicitly noted that the following set of embodiments represents a suitably structured part of the general description directed to preferred aspects of the present invention, and, thus, suitably supports, but does not represent the claims of the present invention.

[0106] 1. Composition comprising

[0107] (a) at least one cyclic ether (CE) with a molecular weight in the range of from 80 to 500 g / mol as component (A) in an amount in the range of from 10 to 80 wt% based on the weight of the composition and

[0108] (b) a urea compound (CU) as component (B) in an amount in the range of from 10 to 80 wt% based on the weight of the composition, wherein the sum of the components of the composition adds up to 100 wt%, wherein the composition is obtained or obtainable by a process at least comprising the steps

[0109] (i) providing a composition (M1) comprising toluene diisocyanate; (ii) adding a composition (M2) comprising at least one monohydroxy compound (CM) of formula (I) to obtain a composition (M3) comprising at least one monoisocyanate adduct, wherein in step (ii) the molar ratio of the at least one monohydroxyl compound of general formula (I) to the toluene diisocyanate is in the range of > 1.0: 1.0 to < 1 .5: 1.0;

[0110] (iii) adding a composition (M4) comprising at least one diamine and at least one cyclic ether (CE) to obtain the urea compound (CU); wherein the monohydroxy compound (CM) has the general formula (I)

[0111] R1-OH (I), wherein

[0112] R1is selected from linear or branched, substituted or unsubstituted C4-C22 alkyl, linear or branched, substituted or unsubstituted C4-C22 alkenyl, substituted or unsubstituted C6-C12 cycloalkyl, linear or branched, substituted or unsubstituted C7-C24 aralkyl, and substituted or unsubstituted Ce-C24 aryl, a radical of formula R11(O-CnH2n)x-, a radical of formula R11[O-C(=O)-CvH2v]x-, and a radical of formula R11(O-CnH2n)x-i [O-C(=O)-CvH2v]x-, wherein

[0113] R11is selected from linear or branched, substituted or unsubstituted C4-C22 alkyl, linear or branched, substituted or unsubstituted C4-C22 alkenyl, substituted or unsubstituted C6-C12 cycloalkyl, linear or branched, substituted or unsubstituted C7-C24 aralkyl, and substituted or unsubstituted Ce-C24 aryl, n is an integer from 2 to 4, x is an integer from 1 to 15, and v is an integer from 4 to 6. The composition according to embodiment 1 , wherein the composition comprises

[0114] (a) the cyclic ether (CE) as component (A) in an amount in the range of from 10 to 80 wt% based on the weight of the composition,

[0115] (b) the urea compound (CU) as component (B) in an amount in the range of from 10 to 80 wt% based on the weight of the composition,

[0116] (c) a salt compound as component (C) in an amount in the range of from 0 to 25 wt% based on the weight of the composition, (d) an organic solvent as component (D) in an amount in the range of from 10 to 50 wt% based on the weight of the composition wherein the solvent used in the process does not comprise further cyclic ethers, wherein the sum of the components of the composition adds up to 100 wt%. The composition according to embodiment 1 or embodiment 2, wherein the cyclic ether is a monocyclic or bicyclic ether having a molecular weight in the range of from 80 to 250 g / mol. The composition according to any one of embodiments 1 to 3, wherein the cyclic ether is selected from the group consisting of Dimethyl isosorbide (DM I) and dihydrolevoglu- cosenone (DHGS). The composition according to any one of embodiments 1 to 4, wherein the toluene diisocyanate is selected from 2, 4-toluene diisocyanate and a mixture of 2, 4-toluene diisocyanate and 2, 6-toluene diisocyanate. The composition according to any one of embodiments 1 to 5, wherein the at least one monohydroxy compound of formula (I) is selected from butyltriglycol, butyldiglycol, butyltetraglycol, butanol, isotridecyl alcohol, oleyl alcohol, Guerbet alcohols containing 8 to 20 carbon atoms, linoleyl alcohol, lauryl alcohol, stearyl alcohol, cyclohexanol, benzyl alcohol, 4-dodecylphenol, ethoxylated triphenylmethanol, ethoxylated 4-dodecylphenol and methoxy polyethylene glycol and mixtures thereof. The composition according to any of embodiments 1 to 6, wherein the at least one diamine is selected from diamines of formula (Ila), (lib), (He), (lid) and (He);

[0117] H2N-R3-NH2(Ha), wherein R3is -CyH2y- and y is an integer from 2 to 12, diamine of formula (Hb) diamines of formula (lie)

[0118] , and diamines of formula (He), wherein, in formula (He), formula (lid) and formula (He), R4are identical or different and are selected from H, CH3-, C2H5- and C3H7-, and R5is selected from -CH2- , -C2H4-, -C3H6- and -CeHi2-. The composition according to any of embodiments 1 to 7, wherein the urea compound (CU) has a weight average molecular weight in the range of > 300 g / mol to < 5000 g / mol, determined according to DIN 55672-2. The composition according to any one of embodiments 2 to 8, wherein the at least one polar aprotic solvent is selected from the group consisting of dimethyl sulfoxide, N,N-dimethylfor- mamide, N,N-dimethylacetamide, N-methylpyrrolidone, N-ethylpyrrolidone, N-propylpyrrol- idone, N-butylpyrrolidone, N,N,N',N'-tetramethylurea, hexamethyl- phosphoric acid triamide and methyl 5-(dimethylamino)-2-methyl-5-oxopentanoate. 10. The composition according to any one of embodiments 2 to 9, wherein the salt is a metal salt selected from the group consisting of lithium chloride, lithium nitrate, lithium bromide, and dioctyl sulfosuccinate sodium salt.

[0119] 11. A process for preparing a composition according to any of embodiments 1 to 10 comprising the steps:

[0120] (i) providing a composition (M1) comprising toluene diisocyanate;

[0121] (ii) adding a composition (M2) comprising at least one monohydroxy compound (CM) of formula (I) to obtain a composition (M3) comprising at least one monoisocyanate adduct, wherein in step (ii) the molar ratio of the at least one monohydroxyl compound of general formula (I) to the toluene diisocyanate is in the range of > 1.0: 1.0 to < 1 .5: 1.0;

[0122] (iii) adding a composition (M4) comprising at least one diamine and at least one cyclic ether (CE) to obtain the urea compound (CU); wherein the monohydroxy compound (CM) has the general formula (I)

[0123] R1-OH (I), wherein

[0124] R1is selected from linear or branched, substituted or unsubstituted C4-C22 alkyl, linear or branched, substituted or unsubstituted C4-C22 alkenyl, substituted or unsubstituted C6-C12 cycloalkyl, linear or branched, substituted or unsubstituted C7-C24 aralkyl, and substituted or unsubstituted Ce-C24 aryl, a radical of formula R11(O-CnH2n)x-, a radical of formula R11[O-C(=O)-CvH2v]x-, and a radical of formula R11(O-CnH2n)x-i [O-C(=O)-CvH2v]x-, wherein

[0125] R11is selected from linear or branched, substituted or unsubstituted C4-C22 alkyl, linear or branched, substituted or unsubstituted C4-C22 alkenyl, substituted or unsubstituted C6-C12 cycloalkyl, linear or branched, substituted or unsubstituted C7-C24 aralkyl, and substituted or unsubstituted Ce-C24 aryl, n is an integer from 2 to 4, x is an integer from 1 to 15, and v is an integer from 4 to 6. A liquid composition comprising > 0.01 wt.-% to < 10.0 wt.-%, based on the total weight of the liquid composition, of the composition according to any one of embodiments 1 to 10; and > 15.0 wt.-% to 99.9 < wt.-%, based on the total weight of the liquid composition of at least one of the components, selected from the group consisting of pigment pastes, binders, fillers, solvents, defoamers, neutralising agent, wetting agent, pigment dispersing agents, preservatives and water. The liquid composition according to embodiment 12, wherein the composition is a paint, water based coating formulations, solvent based coating formulations, lacquer, varnish, paper coating, wood coating, adhesive, ink, cosmetic formulation, detergent formulation, textile, and drilling muds plaster formulations, cement compositions, formulations for plasterboard, for hydraulic binders such as mortar formulations, formulations for ceramics and for leather. Use of the composition according to any one of embodiments 1 to 10 or he composition obtained or obtainable according to the process according to embodiment 11 in liquid compositions as a thixotropic agent for paint and coating formulations, adhesive, paint lacquer, PVC plastisol, ink and cement formulations. Composition comprising

[0126] (a) at least one cyclic ether (CE) selected from the group consisting of monocyclic or bicyclic ethers having a molecular weight in the range of from 80 to 250 g / mol as component (A) in an amount in the range of from 10 to 80 wt% based on the weight of the composition and

[0127] (b) a urea compound (CU) as component (B) in an amount in the range of from 10 to 80 wt% based on the weight of the composition, wherein the sum of the components of the composition adds up to 100 wt%, wherein the composition is obtained or obtainable by a process at least comprising the steps

[0128] (i) providing a composition (M1) comprising toluene diisocyanate; (ii) adding a composition (M2) comprising at least one monohydroxy compound (CM) of formula (I) to obtain a composition (M3) comprising at least one monoisocyanate adduct, wherein in step (ii) the molar ratio of the at least one monohydroxyl compound of general formula (I) to the toluene diisocyanate is in the range of > 1.0: 1.0 to < 1.5: 1.0;

[0129] (iii) adding a composition (M4) comprising at least one diamine and at least one cyclic ether (CE) to obtain the urea compound (CU); wherein the monohydroxy compound (CM) has the general formula (I)

[0130] R1-OH (I), wherein

[0131] R1is selected from linear or branched, substituted or unsubstituted C4-C22 alkyl, linear or branched, substituted or unsubstituted C4-C22 alkenyl, substituted or unsubstituted C6-C12 cycloalkyl, linear or branched, substituted or unsubstituted C7-C24 aralkyl, and substituted or unsubstituted Ce-C24 aryl, a radical of formula R11(O-CnH2n)x-, a radical of formula R11[O-C(=O)-CvH2v]x-, and a radical of formula R11(O-CnH2n)x-i [O-C(=O)-CvH2v]x-, wherein

[0132] R11is selected from linear or branched, substituted or unsubstituted C4-C22 alkyl, linear or branched, substituted or unsubstituted C4-C22 alkenyl, substituted or unsubstituted C6-C12 cycloalkyl, linear or branched, substituted or unsubstituted C7-C24 aralkyl, and substituted or unsubstituted Ce-C24 aryl, n is an integer from 2 to 4, x is an integer from 1 to 15, and v is an integer from 4 to 6. The composition according to embodiment 15, wherein the composition comprises

[0133] (a) the cyclic ether (CE) as component (A) in an amount in the range of from 10 to 80 wt% based on the weight of the composition,

[0134] (b) the urea compound (CU) as component (B) in an amount in the range of from 10 to 80 wt% based on the weight of the composition,

[0135] (c) a salt compound as component (C) in an amount in the range of from 0 to 25 wt% based on the weight of the composition, (d) an organic solvent as component (D) in an amount in the range of from 10 to 50 wt% based on the weight of the composition wherein the solvent used in the process does not comprise further cyclic ethers, wherein the sum of the components of the composition adds up to 100 wt%. The composition according to any one of embodiments 15 to 16, wherein the cyclic ether is selected from the group consisting of Dimethyl isosorbide (DMI) and dihydrolevoglu- cosenone (DHGS). The composition according to any one of embodiments 15 to 17, wherein the toluene diisocyanate is selected from 2, 4-toluene diisocyanate and a mixture of 2, 4-toluene diisocyanate and 2, 6-toluene diisocyanate. The composition according to any one of embodiments 15 to 18, wherein the at least one monohydroxy compound of formula (I) is selected from butyltriglycol, butyldiglycol, butyltetraglycol, butanol, isotridecyl alcohol, oleyl alcohol, Guerbet alcohols containing 8 to 20 carbon atoms, linoleyl alcohol, lauryl alcohol, stearyl alcohol, cyclohexanol, benzyl alcohol, 4-dodecylphenol, ethoxylated triphenylmethanol, ethoxylated 4-dodecylphenol and methoxy polyethylene glycol and mixtures thereof. The composition according to any of embodiments 15 to 19, wherein the at least one diamine is selected from diamines of formula (Ila), (lib), (He), (lid) and (He);

[0136] H2N-R3-NH2(Ila), wherein R3is -CyH2y- and y is an integer from 2 to 12, diamine of formula (Hb) diamines of formula (lie)

[0137] , and diamines of formula (He), wherein, in formula (He), formula (lid) and formula (He), R4are identical or different and are selected from H, CH3-, C2H5- and C3H7-, and R5is selected from -CH2- , -C2H4-, -C3H6- and -CeHi2-. The composition according to any of embodiments 15 to 20, wherein the urea compound (CU) has a weight average molecular weight in the range of > 300 g / mol to < 5000 g / mol, determined according to DIN 55672-2. The composition according to any one of embodiments 16 to 21 , wherein the at least one polar aprotic solvent is selected from the group consisting of dimethyl sulfoxide, N,N-dime- thylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N-ethylpyrrolidone, N- propylpyrrolidone, N-butylpyrrolidone, N,N,N',N'-tetramethylurea, hexamethyl- phosphoric acid triamide and methyl 5-(dimethylamino)-2-methyl-5-oxopentanoate. The composition according to any one of embodiments 16 to 22, wherein the metal salt catalyst is selected from the group consisting of lithium chloride, lithium nitrate, lithium bromide, and dioctyl sulfosuccinate sodium salt. A process for preparing a composition according to any of embodiments 15 to 23 comprising the steps:

[0138] (i) providing a composition (M1) comprising toluene diisocyanate;

[0139] (ii) adding a composition (M2) comprising at least one monohydroxy compound (CM) of formula (I) to obtain a composition (M3) comprising at least one monoisocyanate adduct, wherein in step (ii) the molar ratio of the at least one monohydroxyl compound of general formula (I) to the toluene diisocyanate is in the range of > 1.0: 1.0 to < 1.5: 1.0;

[0140] (iii) adding a composition (M4) comprising at least one diamine and at least one cyclic ether (CE) selected from the group consisting of monocyclic or bicyclic ethers having a molecular weight in the range of from 80 to 250 g / mol to obtain the urea compound (CU); wherein the monohydroxy compound (CM) has the general formula (I)

[0141] R1-OH (I), wherein

[0142] R1is selected from linear or branched, substituted or unsubstituted C4-C22 alkyl, linear or branched, substituted or unsubstituted C4-C22 alkenyl, substituted or unsubstituted C6-C12 cycloalkyl, linear or branched, substituted or unsubstituted C7-C24 aralkyl, and substituted or unsubstituted Ce-C24 aryl, a radical of formula R11(O-CnH2n)x-, a radical of formula R11[O-C(=O)-CvH2v]x-, and a radical of formula R11(O-CnH2n)x-i [O-C(=O)-CvH2v]x-, wherein

[0143] R11is selected from linear or branched, substituted or unsubstituted C4-C22 alkyl, linear or branched, substituted or unsubstituted C4-C22 alkenyl, substituted or unsubstituted C6-C12 cycloalkyl, linear or branched, substituted or unsubstituted C7-C24 aralkyl, and substituted or unsubstituted Ce-C24 aryl, n is an integer from 2 to 4, x is an integer from 1 to 15, and v is an integer from 4 to 6. 25. A liquid composition comprising > 0.01 wt.-% to < 10.0 wt.-%, based on the total weight of the liquid composition, of the composition according to any one of embodiments 15 to 23; and > 15.0 wt.-% to 99.9 < wt.-%, based on the total weight of the liquid composition of at least one of the components, selected from the group consisting of pigment pastes, binders, fillers, solvents, defoamers, neutralising agent, wetting agent, pigment dispersing agents, preservatives and water.

[0144] 26. The liquid composition according to embodiment 25, wherein the composition is a paint, water based coating formulations, solvent based coating formulations, lacquer, varnish, paper coating, wood coating, adhesive, ink, cosmetic formulation, detergent formulation, textile, and drilling muds plaster formulations, cement compositions, formulations for plasterboard, for hydraulic binders such as mortar formulations, formulations for ceramics and for leather.

[0145] 27. Use of the composition according to any one of embodiments 15 to 23 or the composition obtained or obtainable according to the process according to embodiment 24 in liquid compositions as a thixotropic agent for paint and coating formulations, adhesive, paint lacquer, PVC plastisol, ink and cement formulations.

[0146] 28. Composition comprising

[0147] (a) at least one cyclic ether (CE) selected from the group consisting of dimethyl isosorbide (DMI) and dihydrolevoglucosenone (DHGS) as component (A) in an amount in the range of from 10 to 80 wt% based on the weight of the composition and

[0148] (b) a urea compound (CU) as component (B) in an amount in the range of from 10 to 80 wt% based on the weight of the composition, wherein the sum of the components of the composition adds up to 100 wt%, wherein the composition is obtained or obtainable by a process at least comprising the steps

[0149] (i) providing a composition (M1) comprising toluene diisocyanate;

[0150] (ii) adding a composition (M2) comprising at least one monohydroxy compound (CM) of formula (I) to obtain a composition (M3) comprising at least one monoisocyanate adduct, wherein in step (ii) the molar ratio of the at least one monohydroxyl compound of general formula (I) to the toluene diisocyanate is in the range of > 1.0: 1.0 to < 1.5:

[0151] 1.0; (iii) adding a composition (M4) comprising at least one diamine, at least one cyclic ether (CE) to obtain the urea compound (CU); wherein the monohydroxy compound (CM) has the general formula (I)

[0152] R1-OH (I), wherein

[0153] R1is selected from linear or branched, substituted or unsubstituted C4-C22 alkyl, linear or branched, substituted or unsubstituted C4-C22 alkenyl, substituted or unsubstituted C6-C12 cycloalkyl, linear or branched, substituted or unsubstituted C7-C24 aralkyl, and substituted or unsubstituted Ce-C24 aryl, a radical of formula R11(O-CnH2n)x-, a radical of formula R11[O-C(=O)-CvH2v]x-, and a radical of formula R11(O-CnH2n)x-i [O-C(=O)-CvH2v]x-, wherein

[0154] R11is selected from linear or branched, substituted or unsubstituted C4-C22 alkyl, linear or branched, substituted or unsubstituted C4-C22 alkenyl, substituted or unsubstituted C6-C12 cycloalkyl, linear or branched, substituted or unsubstituted C7-C24 aralkyl, and substituted or unsubstituted Ce-C24 aryl, n is an integer from 2 to 4, x is an integer from 1 to 15, and v is an integer from 4 to 6.

[0155] 29. The composition according to embodiment 28, wherein the composition comprises

[0156] (a) the cyclic ether (CE) as component (A) in an amount in the range of from 10 to 80 wt% based on the weight of the composition,

[0157] (b) the urea compound (CU) as component (B) in an amount in the range of from 10 to 80 wt% based on the weight of the composition,

[0158] (c) a salt compound as component (C) in an amount in the range of from 0 to 25 wt% based on the weight of the composition,

[0159] (d) an organic solvent as component (D) in an amount in the range of from 10 to 50 wt% based on the weight of the composition wherein the solvent used in the process does not comprise further cyclic ethers, wherein the sum of the components of the composition adds up to 100 wt%. 30. The composition according to any one of embodiments 28 to 29, wherein the toluene diisocyanate is selected from 2, 4-toluene diisocyanate and a mixture of 2, 4-toluene diisocyanate and 2, 6-toluene diisocyanate.

[0160] 31 . The composition according to any one of embodiments 28 to 30, wherein the at least one monohydroxy compound of formula (I) is selected from butyltriglycol, butyldiglycol, butyltetraglycol, butanol, isotridecyl alcohol, oleyl alcohol, Guerbet alcohols containing 8 to 20 carbon atoms, linoleyl alcohol, lauryl alcohol, stearyl alcohol, cyclohexanol, benzyl alcohol, 4-dodecylphenol, ethoxylated triphenylmethanol, ethoxylated 4-dodecylphenol and methoxy polyethylene glycol and mixtures thereof.

[0161] 32. The composition according to any of embodiments 28 to 31 , wherein the at least one diamine is selected from diamines of formula (Ila), (lib), (He), (lid) and (He);

[0162] H2N-R3-NH2(Ha), wherein R3is -CyH2y- and y is an integer from 2 to 12, diamine of formula (lib) diamines of formula (Hd)

[0163] , and diamines of formula (lie), wherein, in formula (He), formula (lid) and formula (He), R4are identical or different and are selected from H, CH3-, C2H5- and C3H7-, and R5is selected from -CH2- , -C2H4-, -C3H6- and -CeHi2-. The composition according to any of embodiments 28 to 32, wherein the urea compound (CU) has a weight average molecular weight in the range of > 300 g / mol to < 5000 g / mol, determined according to DIN 55672-2. The composition according to any one of embodiments 29 to 33, wherein the at least one polar aprotic solvent is selected from the group consisting of dimethyl sulfoxide, N,N-dime- thylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N-ethylpyrrolidone, N- propylpyrrolidone, N-butylpyrrolidone, N,N,N',N'-tetramethylurea, hexamethyl- phosphoric acid triamide and methyl 5-(dimethylamino)-2-methyl-5-oxopentanoate. The composition according to any one of embodiments 29 to 34, wherein the salt is a metal salt selected from the group consisting of lithium chloride, lithium nitrate, lithium bromide, and dioctyl sulfosuccinate sodium salt. A process for preparing a composition according to any of embodiments 28 to 35 comprising the steps:

[0164] (i) providing a composition (M1) comprising toluene diisocyanate;

[0165] (ii) adding a composition (M2) comprising at least one monohydroxy compound (CM) of formula (I) to obtain a composition (M3) comprising at least one monoisocyanate adduct, wherein in step (ii) the molar ratio of the at least one monohydroxyl compound of general formula (I) to the toluene diisocyanate is in the range of > 1.0: 1.0 to < 1.5:

[0166] 1.0; (iii) adding a composition (M4) comprising at least one diamine and at least one cyclic ether (CE) selected from the group consisting of dimethyl isosorbide (DMI) and di- hydrolevoglucosenone (DHGS) to obtain the urea compound (CU); wherein the monohydroxy compound (CM) has the general formula (I)

[0167] R1-OH (I), wherein

[0168] R1is selected from linear or branched, substituted or unsubstituted C4-C22 alkyl, linear or branched, substituted or unsubstituted C4-C22 alkenyl, substituted or unsubstituted C6-C12 cycloalkyl, linear or branched, substituted or unsubstituted C7-C24 aralkyl, and substituted or unsubstituted Ce-C24 aryl, a radical of formula R11(O-CnH2n)x-, a radical of formula R11[O-C(=O)-CvH2v]x-, and a radical of formula R11(O-CnH2n)x-i [O-C(=O)-CvH2v]x-, wherein

[0169] R11is selected from linear or branched, substituted or unsubstituted C4-C22 alkyl, linear or branched, substituted or unsubstituted C4-C22 alkenyl, substituted or unsubstituted C6-C12 cycloalkyl, linear or branched, substituted or unsubstituted C7-C24 aralkyl, and substituted or unsubstituted Ce-C24 aryl, n is an integer from 2 to 4, x is an integer from 1 to 15, and v is an integer from 4 to 6.

[0170] 37. A liquid composition comprising > 0.01 wt.-% to < 10.0 wt.-%, based on the total weight of the liquid composition, of the composition according to any one of embodiments 28 to 35; and > 15.0 wt.-% to 99.9 < wt.-%, based on the total weight of the liquid composition of at least one of the components, selected from the group consisting of pigment pastes, binders, fillers, solvents, defoamers, neutralising agent, wetting agent, pigment dispersing agents, preservatives and water.

[0171] 38. The liquid composition according to embodiment 37, wherein the composition is a paint, water based coating formulations, solvent based coating formulations, lacquer, varnish, paper coating, wood coating, adhesive, ink, cosmetic formulation, detergent formulation, textile, and drilling muds plaster formulations, cement compositions, formulations for plasterboard, for hydraulic binders such as mortar formulations, formulations for ceramics and for leather. 39. Use of the composition according to any one of embodiments 28 to 35 or the composition obtained or obtainable according to the process according to embodiment 36 in liquid compositions as a thixotropic agent for paint and coating formulations, adhesive, paint lacquer, PVC plastisol, ink and cement formulations.

[0172] Illustrative embodiments of the present invention are listed below, but these do not restrict the present invention. In particular, the present invention also encompasses those embodiments which result from the dependency references and hence combinations specified hereinafter.

[0173] Examples

[0174] TDI T100: 2,4-toluene diisocyanate (TDI) from Covestro

[0175] TDI T80: isomer mixture of 2,4- and 2,6- toluene diisocyanate (TDI)from BASF.

[0176] TDI T98, T97, T96, T95 et. al are a blend of TDI T100 and TDI T80. For example, T98 is a blend of TDI T100 and TDI T80 with the ratio of 90: 10, and T90 is a blend of TDI T100 and TDI T80 with the ratio of 50:50.

[0177] Example 1

[0178] In a 5-necked 200 ml Sulfier flask with an overhead stirrer, thermometer, reflux condenser and septum, the ‘Isocyanate’ 17.4 g TDI T 100 (100 mmol) and 10 g of ethyl acetate was purged with nitrogen. ‘Alcohol’ 21.6 g butyl triglycol (BTG) (105 mmol) was fed to the reactor over a time period of 10 hours at a temperature 45°C. The molar ratio of monohydroxyl compound R-OH to TDI is 1 .05: 1. The reaction was exothermic and the internal temperature was kept lower than 50°C. After the completion of the feed, the reaction was continued until the NCO value (NCO%) reaching to the theoretical calculated value (theoretically, half amount of NCO groups from TDI was consumed in this step). ‘Salt’ 2.6 g lithium nitrate, ‘Diamine’ 6.2 g m-xylylene diamine (m- XDA) (46 mmol), and ‘Cyclic ether’ (and for examples 2 to 19 optionally ‘Solvent’) 70 g dimethyl isosorbide (DMI) were mixed at room temperature. The resulting mixture was fed into the monoisocyanate adduct obtained at a temperature at 60°C. The reaction was exothermic and the internal temperature was kept lower than 80°C. The resulting mixture was heated to a temperature of 80°C and held until the NCO value is 0%. Then ethyl acetate was distilled out under vacuum. The resulting urea urethane polymer (product) was a yellowish transparent liquid and was free flowing at room temperature. The product remained stable (no precipitation or gel formation) upon storage (>1 months) under ambient conditions.

[0179] The molecular weight of example 1 was 2070 g / mol as determined by GPC (according to DIN 55672-2, N,N-Dimethylacetamide, 1mL / min, PMMA standard); and its PDI was 1.1.

[0180] Examples 2 to 19 Examples 2 to 19 were prepared in a manner similar to Example 1 with variations in amounts and type of Isocyanate, Alcohol’, Salt’, ‘Diamine’, ‘Cyclic ether’, and ‘Solvent’. Table 1 provides details of the representative examples 2 to 19 according to the process of the present invention.

[0181] Table 1

[0182] Comparative Example 1 : In a 5-necked 200 ml Sulfier flask with an overhead stirrer, thermometer, reflux condenser and septum, 17.4 g of TDI (TDI isomers (in wt.-%) 2, 4 isomer:94, 2, 6 isomer: 6) and 10 g of ethyl acetate was purged with nitrogen. 21.6 g of butyl triglycol (BTG) (105 mmol) was fed to the reactor over a time period of 3 hours at a temperature of 45°C. The molar ratio of monohydroxyl compound R-OH to TDI is 1.05: 1. The reaction was exothermic and the internal temperature was kept lower than 50°C. After the completion of the feed, the reaction was continued until the NCO value (NCO%) of 8.6% was reached. 2.6 g lithium nitrate, 6.2 g of m-xylylene diamine (m- XDA) (46 mmol) and 48 g of dimethyl sulfoxide (DMSO), were mixed at room temperature. The resulting mixture was fed into the monoisocyanate adduct obtained at a temperature of 60°C. The reaction was exothermic and the internal temperature was kept lower than 80°C. The resulting mixture was heated to a temperature of 80°C and held until the NCO value is 0%. Then ethyl acetate was distilled out under vacuum. The resulting urea urethane polymer (product) was a yellowish transparent liquid and was free flowing at room temperature. The product remained stable (no precipitation or gel formation) upon storage (>2 months) under ambient conditions.

[0183] Comparative Example 2:

[0184] Preparation of urea urethane compound C2

[0185] In a 5-necked 200 ml Sulfier flask with an overhead stirrer, thermometer, reflux condenser and septum, a mixture containing 17.4 g of TDI T100 (100 mmol) and 10 g of ethyl acetate was purged with nitrogen. 5.4 g Butyltriglycol ether (26.2 mmol), 13.8 g of poly(ethylene glycol) methyl ether (MW of 350 g / mol 39.4 mmol), 19.7 g of poly(ethylene glycol) methyl ether (MW of 500 g / mol 38.4 mmol) and 0.03 g p-toluenesulfonic were mixed and the mixture of alcohols was fed to the reactor over a time period of 10 hours at 45°C. The resultant mixture was stirred at 45°C until the NCO value (NCO%) was stable, to obtain a reaction mixture comprising a mixture of monoisocyanate adducts.

[0186] 2.6 g Lithium nitrate, 6.2 g of m-xylenediamine (46 mmol) and 65 g dimethyl sulfoxide were mixed at room temperature and the mixture was fed to the reaction mixture comprising a mixture of mo-noisocyanate adducts at 60°C over a time period of 5 hours. The resulting mixture was heated to 80°C and stirred at the same temperature until the NCO content was 0.

[0187] Ethyl acetate was distilled out under reduced pressure to obtain C2 as a yellowish transparent liquid that was free flowing at room temperature.

[0188] The molecular weight of U6 was 2900g / mol as determined by GPC (according to DIN 55672-2, N,N-Dimethylacetamide, 1 mL / min, PMMA standard); and its PDI was 1.3.

[0189] The urea urethane compound C2 remained stable (no precipitation or gel formation) upon storage (>2 months) under ambient conditions.

[0190] Performance test: For solvent based application, the coating solution (Formulation 1 , prepared according to table 2) was stirred via Dispermat for 5 min @ 2000 rpm, and then kept at standby overnight at room temperature before measuring the viscosity. The Examples prepared was added to study the thixotropic effect of the additive on the coatings. Formulation 2 was prepared identical to formulation 1 , but without addition of the Example. Formulation 2 without the Example was treated as a reference.

[0191] The shear jumping measurement starts with the shear rate of 0.05 s-1 for 200 seconds, and then immediately apply a high shear rate of 250 s-1 for 60 seconds, and immediately thereafter, the shear rate was reduced to 0.05 s-1 for 200 seconds.

[0192] To study the thixotropic effect of the Examples, the viscosity was measured at the following intervals: i) Viscosity at t = 199 sec, just before the high shear is applied ii) Viscosity t= 201 sec, just after high shear is applied iii) Viscosity at t= 259 sec, just after high shear is removed iv) Viscosity t= 450 sec, well after high shear is removed.

[0193] Table 2

[0194] The viscosity measurements at different time intervals are provided in Table 3.

[0195] For water-based application, a formulation for the viscosity measurement was prepared by adding 0.6wt% of Examples into water. The mixture was shaken by hand for 30 seconds and then allowed to standby overnight at room temperature before measuring the viscosity (shear jumping test as above). The viscosity measurements at different time intervals are provided in Table 3.

[0196] As is evident from the results provided in above tables, the viscosity of formulation with examples dropped significantly immediately after high shear (i.e. 250 s-1 for 60 seconds) was applied. Immediately after the high shear was removed, an increase in viscosity was observed. This means formulation with the examples exhibited a significant recovery of the viscosity.

[0197] Thus, the Examples prepared according to the process of the present invention upon addition to formulation imparted thixotropic effect to said formulation which is demonstrated by the drop in viscosity immediately after applying shear stress and gradual recovery of viscosity as a function of time upon removal of shear stress. All the examples according to the present invention remained stable (no precipitation or gel formation) upon storage (>1 months) under ambient conditions.

[0198] Literature cited:

[0199] US 4,383,068

[0200] US 3,893,956

[0201] US 4,522,986

[0202] EP 0 006 252

[0203] US 6,420,466

[0204] W02020 / 182944 H. Machemer, Angewandte Chemie, Vol. 64, pages 213-220 (1952)

[0205] G. Dieckelmann and H.J. Heinz in "The Basics of Industrial Oleochemistry", pages 145-145 (1988)

[0206] Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, Vol. A18, pp. 368-426, VCH, Weinheim 1991 , Germany

Claims

Claims1. Composition comprising(a) at least one cyclic ether (CE) with a molecular weight in the range of from 80 to 500 g / mol as component (A) in an amount in the range of from 10 to 80 wt% based on the weight of the composition and(b) a urea compound (CU) as component (B) in an amount in the range of from 10 to 80 wt% based on the weight of the composition, wherein the sum of the components of the composition adds up to 100 wt%, wherein the composition is obtained or obtainable by a process at least comprising(i) providing a composition (M1) comprising toluene diisocyanate;(ii) adding a composition (M2) comprising at least one monohydroxy compound (CM) of formula (I) to obtain a composition (M3) comprising at least one monoisocyanate adduct, wherein in step (ii) the molar ratio of the at least one monohydroxyl compound of general formula (I) to the toluene diisocyanate is in the range of > 1.0: 1.0 to < 1.5: 1.0;(iii) adding a composition (M4) comprising at least one diamine and at least one cyclic ether (CE) to obtain the urea compound (CU); wherein the monohydroxy compound (CM) has the general formula (I)R1-OH (I), whereinR1is selected from linear or branched, substituted or unsubstituted C4-C22 alkyl, linear or branched, substituted or unsubstituted C4-C22 alkenyl, substituted or unsubstituted C6-C12 cycloalkyl, linear or branched, substituted or unsubstituted C7-C24 aralkyl, and substituted or unsubstituted Ce-C24 aryl, a radical of formula R11(O-CnH2n)x-, a radical of formula R11[O-C(=O)-CvH2v]x-, and a radical of formula R11(O-CnH2n)x-i [O-C(=O)-CvH2v]x-, whereinR11is selected from linear or branched, substituted or unsubstituted C4-C22 alkyl, linear or branched, substituted or unsubstituted C4-C22 alkenyl, substituted or unsubstituted C6-C12 cycloalkyl, linear or branched, substituted or unsubstituted C7-C24 aralkyl, and substituted or unsubstituted Ce-C24 aryl, n is an integer from 2 to 4, x is an integer from 1 to 15, and v is an integer from 4 to 6.

2. The composition according to claim 1 , wherein the composition comprises(a) the cyclic ether (CE) as component (A) in an amount in the range of from 10 to 80 wt% based on the weight of the composition,(b) the urea compound (CU) as component (B) in an amount in the range of from 10 to 80 wt% based on the weight of the composition,(c) a salt compound as component (C) in an amount in the range of from 0 to 25 wt% based on the weight of the composition,(d) an organic solvent as component (D) in an amount in the range of from 10 to 50 wt% based on the weight of the composition wherein the solvent used in the process does not comprise further cyclic ethers, wherein the sum of the components of the composition adds up to 100 wt%.

3. The composition according to claim 1 or claim 2, wherein the cyclic ether (CE) is a mono- cyclic or bicyclic ether having a molecular weight in the range of from 80 to 250 g / mol.

4. The composition according to any one of claims 1 to 3, wherein the cyclic ether (CE) is selected from the group consisting of dimethyl isosorbide (DMI) and dihydrolevoglu- cosenone (DHGS).

5. The composition according to any one of claims 1 to 4, wherein the toluene diisocyanate is selected from 2, 4-toluene diisocyanate and a mixture of 2, 4-toluene diisocyanate and 2, 6-toluene diisocyanate.

6. The composition according to any one of claims 1 to 5, wherein the at least one monohydroxy compound of formula (I) is selected from the group consisting of butyltriglycol, butyldiglycol, butyltetraglycol, butanol, isotridecyl alcohol, oleyl alcohol, Guerbet alcohols contain-ing 8 to 20 carbon atoms, linoleyl alcohol, lauryl alcohol, stearyl alcohol, cyclohexanol, benzyl alcohol, 4-dodecylphenol, ethoxylated triphenylmethanol, ethoxylated 4-dodecylphenol and methoxy polyethylene glycol and mixtures thereof.

7. The composition according to any of claims 1 to 6, wherein the at least one diamine is selected from diamines of formula (Ila), (lib), (He), (lid) and (He);H2N-R3-NH2(Ha), wherein R3is -CyH2y- and y is an integer from 2 to 12, diamines of formula (Hb)diamines of formula (Hd)wherein, in formula (He), formula (lid) and formula (He), R4are identical or different and are selected from H, CH3-, C2H5- and C3H7-, and R5is selected from -CH2- , -C2H4-, -C3H6- and -CeHi2-.

8. The composition according to any of claims 1 to 7, wherein the urea compound (CU) has a weight average molecular weight in the range of > 300 g / mol to < 5000 g / mol, determined according to DIN 55672-2.

9. The composition according to any one of claims 2 to 8, wherein the at least one solvent (D) is a polar aprotic solvent, preferably a polar aprotic solvent selected from the group consisting of dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrol- idone, N-ethylpyrrolidone, N-propylpyrrolidone, N-butylpyrrolidone, N,N,N',N'-tetra- methylurea, hexamethyl- phosphoric acid triamide and methyl 5-(dimethylamino)-2-methyl- 5-oxopentanoate.

10. The composition according to any one of claims 2 to 9, wherein the salt is a metal salt selected from the group consisting of lithium chloride, lithium nitrate, lithium bromide, and dioctyl sulfosuccinate sodium salt.

11. A process for preparing a composition according to any of claims 1 to 10 comprising:(i) providing a composition (M1) comprising toluene diisocyanate;(ii) adding a composition (M2) comprising at least one monohydroxy compound (CM) of formula (I) to obtain a composition (M3) comprising at least one monoisocyanate adduct, wherein in step (ii) the molar ratio of the at least one monohydroxyl compound of general formula (I) to the toluene diisocyanate is in the range of > 1.0: 1 .0 to < 1 .5:1.0;(iii) adding a composition (M4) comprising at least one diamine and at least one cyclic ether (CE) to obtain the urea compound (CU); wherein the monohydroxy compound (CM) has the general formula (I)R1-OH (I), whereinR1is selected from linear or branched, substituted or unsubstituted C4-C22 alkyl, linear or branched, substituted or unsubstituted C4-C22 alkenyl, substituted or unsubstituted C6-C12 cycloalkyl, linear or branched, substituted or unsubstituted C7-C24 aralkyl, and substituted or unsubstituted Ce-C24 aryl, a radical of formula11(O-CnH2n)x-, a radical of formula R11[O-C(=O)-CvH2v]x-, and a radical of formula R11(O-CnH2n)x-i [O-C(=O)-CvH2v]x-, whereinR11is selected from linear or branched, substituted or unsubstituted C4-C22 alkyl, linear or branched, substituted or unsubstituted C4-C22 alkenyl, substituted or unsubstituted C6-C12 cycloalkyl, linear or branched, substituted or unsubstituted C7-C24 aralkyl, and substituted or unsubstituted Ce-C24 aryl, n is an integer from 2 to 4, x is an integer from 1 to 15, and v is an integer from 4 to 6.

12. A liquid composition comprising the composition according to any one of claims 1 to 10 in an amount of from > 0.01 wt.-% to < 10.0 wt.-%, based on the total weight of the liquid composition; and at least one component selected from the group consisting of pigment pastes, binders, fillers, solvents, defoamers, neutralising agents, wetting agents, pigment dispersing agents, preservatives and water in an amount of rom > 15.0 wt.-% to 99.9 < wt- %, based on the total weight of the liquid composition.

13. The liquid composition according to claim 12, wherein the composition is a paint, water based coating formulations, solvent based coating formulations, lacquer, varnish, paper coating, wood coating, adhesive, ink, cosmetic formulation, detergent formulation, textile, and drilling muds plaster formulations, cement compositions, formulations for plasterboard, for hydraulic binders such as mortar formulations, formulations for ceramics and for leather.

14. Use of the composition according to any one of claims 1 to 10 or the composition obtained or obtainable according to the process according to claim 11 in liquid compositions as a thixotropic agent for paint and coating formulations, adhesive, paint lacquer, PVC plastisol, ink and cement formulations.

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