Compositions comprising cyclic amides

Abstract

The present invention relates to a composition comprising: a cyclic amide comprising at least one amide NH group; a solvent different from a cyclic amide comprising at least one amide NH group, and wherein the solvent comprises at least one amide group wherein the amide nitrogen of the amide group has two substituents wherein the substituents are selected from aliphatic and aromatic groups, sulfoxide groups; and a urea compound having a number average molecular weight of at least 350 g / mol.

Description

[0001] The present invention relates to a composition comprising a cyclic amide, a solvent and a urea compound. It also relates to the use of the composition for controlling the rheology of a liquid composition, the liquid composition and a coated article.

[0002] In the fields of coating materials, adhesives, sealants and molding compounds as well as non-aqueous oil drilling fluids, it is necessary to tailor the rheological properties of such liquid systems, mainly by adjusting the viscosity. This can be achieved by selecting the concentration of binders, solvents and pigments and / or fillers. Often, so-called rheological additives need to be added to these liquids. The role of these additives is to adjust the rheological properties of the system, such as viscosity and viscoelasticity. By doing so, system properties are usually improved, including anti-sagging, increased storage stability (due to reduced solid particle sedimentation) or a general increase in viscosity (commonly referred to as "thickening").

[0003] The rheology of liquid systems is usually controlled using clays (e.g. bentonites) and / or silica (optionally organomodified), hydrogenated castor oil and polyamide waxes. The disadvantage of these rheology control additives is that they are mostly dry solids that have to be processed into semi-finished product forms using solvents and shear forces and / or introduced into the liquid system by targeted temperature control. Failure to adhere to these temperatures and / or appropriate incorporation conditions will not only lead to poor rheological properties, but also to impaired product properties.

[0004] If the liquid system is a coating composition, these rheology control additives often lead to clouding and hazing of the clear coat. Furthermore, working with dry powdered products can be technically disadvantageous since these products generate dust during processing.

[0005] Liquid application alternatives to these rheology control additives are solutions of specific urea components, as described, for example, in EP 1 188 779 A. Polar / aprotic solvents are usually used as solvents and / or carrier media. Alternatively, ionic liquids can be used instead of conventional organic diluents, as described in DE 10 2008 059 702 A.

[0006] Another aspect that should be noted with respect to rheology control agents provided in liquid form is their storage stability. For example, prolonged storage time or increased storage stress (e.g., storage under temperature changes) may result in reduced storage stability and, at the same time, reduced efficacy in the target system. Therefore, it is desirable that the rheology control agent has good storage stability and is not prone to precipitation during storage.

[0007] To prevent early precipitation during storage, small amounts of salt, especially halides such as LiCl, are often added as stabilizers. Salts can also cause many problems with application performance, especially halides such as LiCl. These ionic compounds can have a negative impact on performance, such as corrosion caused by the coating system, the resistance of the coating material to environmental influences, discoloration and whitening, contamination or conductivity.

[0008] All of these parameters limit the selection of suitable formulations. Therefore, the selection of suitable rheology control additives is difficult, since these additives must be particularly compatible with the subsequent application system and need to meet a variety of requirements. They must not only show improved rheological activity in the application system, but also must show a wide range of compatibility in application-related formulations. There is still a need to continuously provide improved rheology additives. The use of improved rheology additives should result in a very reliable and enhanced thickening effect in a wide range of formulations, while at the same time the storage stability of these rheology control additives needs to be good.

[0009] Therefore, a specific object of the present invention is to provide a high quality rheology control agent with good effects, which can be used in a variety of application systems. More specifically, the present invention is to find a rheology control agent with significant anti-sagging behavior. Another object of the present invention is to provide a rheology control agent that can improve storage stability. Another object of the present invention is to provide a rheology control agent that is essentially free of salt.

[0010] Surprisingly, it has been found that these objects can be achieved by a composition comprising a cyclic amide containing at least one amide NH group; a solvent different from the cyclic amide containing at least one amide NH group, wherein the solvent comprises at least one of an amide group and a sulfoxide group, wherein the amide nitrogen of the amide group has two substituents, wherein the substituents are selected from aliphatic and aromatic groups; and a urea compound having a number average molecular weight of at least 350 g / mol.

[0011] Urea compounds are compounds containing at least one urea group. In one embodiment, the urea compound is a urea-carbamate compound. In another embodiment, the urea component includes a molecule containing at least one urea group and at least one carbamate group. In another embodiment, the urea component includes a molecule containing at least one urea group and at least two carbamate groups. In another embodiment, the urea component includes a molecule containing at least two urea groups; in a different embodiment, the urea compound includes two urea groups and two carbamate groups; in yet another embodiment, the urea component includes a molecule containing at least four urea groups or more than four urea groups. In different embodiments, the urea component includes a molecule containing at least two urea groups and at least two carbamate groups. In different embodiments of the present invention, the carbamate group may not even be present.

[0012] Suitably, the urea-based compound according to claim 11 of WO 2015 / 158407, claim 13 of WO 2015 / 158407, claim 16 of WO 2015 / 158407 and claim 1 of EP 1 396 510 A1 is employed.

[0013] A preferred class of urea compounds can be described according to the following general formula (U-1):

[0014] R31-[R33-Z-R34-W-] n -R32(U-1)

[0015] in

[0016] R31 and R32 are each independently of the other and independently at each occurrence represent a branched or unbranched, saturated or unsaturated organic radical containing 1 to 100 carbon atoms and each having not more than one urea group and not more than one urethane group,

[0017] R33 and R34 independently of one another and independently at each occurrence represent a branched or unbranched polyester radical containing 1 to 300 carbon atoms and optionally containing an ether radical, a branched or unbranched polyether radical containing 2 to 300 carbon atoms, a branched or unbranched polyamide radical containing 1 to 300 carbon atoms, a polysiloxane radical containing 3 to 100 silicon atoms, a branched or unbranched C2 to C22 alkylene radical, a branched or unbranched C2 to C22 cycloalkylene radical, a branched or unbranched C2 to C18 alkenylene radical, a C6 to C12 arylene radical and / or a branched or unbranched C7 to C22 arylene alkyl radical,

[0018] Z and W independently represent NH—CO—O and / or NH—CO—NH. When Z and W appear in plural, Z and W independently represent the above groups.

[0019] n represents an integer of 1 to 150, preferably 2 to 150, and when n appears in plural, n independently represents an integer of 1 to 150, preferably 2 to 150.

[0020] In another preferred embodiment, the urea compound is selected from the group consisting of formulae (U-2a), (U-2b), (U-2c), (U-2d) and (U-2e).

[0021]

[0022] in

[0023] AM is selected from linear or branched, saturated or unsaturated, aliphatic, cycloaliphatic, aromatic or aliphatic-aromatic organic radicals having 2 to 50 C atoms. If AM occurs multiple times, AM is independently selected from linear or branched, saturated or unsaturated, aliphatic, cycloaliphatic, aromatic or aliphatic-aromatic organic radicals having 2 to 50 C atoms.

[0024] AM1 and AM2 independently of one another represent a linear or branched, saturated or unsaturated, aliphatic, aromatic or aliphatic-aromatic organic radical having 1 to 50 C atoms. If AM1 and AM2 occur multiple times, AM1 and AM2 independently represent the above radicals.

[0025] IC1 and IC2 independently represent a linear or branched, saturated or unsaturated, aliphatic, aromatic or aliphatic-aromatic hydrocarbon radical having 2 to 40 C atoms. If IC1 and IC2 occur multiple times, IC1 and IC2 independently represent the above radicals.

[0026] IC3 represents a linear or branched, saturated or unsaturated, aliphatic, aromatic or aliphatic-aromatic hydrocarbon group having 2 to 24 carbon atoms. If IC3 appears in multiple groups, IC3 independently represents a linear or branched, saturated or unsaturated, aliphatic, aromatic or aliphatic-aromatic hydrocarbon group having 2 to 24 carbon atoms.

[0027] IC4 is selected from the group as described for IC1 and IC2 or a carbamate group-containing fragment having the structure

[0028] -[IC2-NH-(C=O)-O-RP3-O-(C=O)-NH-IC2]-

[0029] Wherein RP3 represents a straight-chain or branched, saturated or unsaturated, aliphatic, aromatic or aliphatic-aromatic organic group having 2 to 24 C atoms and / or a (poly)ether group having 1 to 120 ether oxygen atoms and / or a polyamide group having 1 to 100 amide groups and / or a polysiloxane group having 3 to 100 silicon atoms and / or a polyester alkyl group having 1 to 100 ester groups and optionally containing ether groups. When RP3 appears in multiple numbers, RP3 independently represents the above groups.

[0030] RP1 and RP2 independently represent a linear or branched, saturated or unsaturated, aliphatic, aromatic or aliphatic-aromatic organic group having 1 to 24 C atoms and / or a polyether group having 1 to 120 ether oxygen atoms and / or a polyester group having 1 to 100 ester groups and optionally containing ether groups, and / or a polyamide group having 1 to 100 amide groups, and / or a polysiloxane group having 3 to 100 silicon atoms. In the case of a plurality of occurrences of RP1 and RP2, RP1 and RP2 independently represent the above groups.

[0031] RP3 represents a linear or branched, saturated or unsaturated, aliphatic, aromatic or aliphatic-aromatic organic group having 2 to 24 C atoms and / or a (poly)ether group having 1 to 120 ether oxygen atoms and / or a polyamide group having 1 to 100 amide groups and / or a polysiloxane group having 3 to 100 silicon atoms and / or a polyester group having 1 to 100 ester groups and optionally containing ether groups, and in the case of a plurality of occurrences of RP3, RP3 independently represents the above groups, and

[0032] m is an integer of 0 to 20, preferably 1 to 20, more preferably 1 to 5. p represents 0 and / or 1. q is an integer of 0 to 20.

[0033] Preferably, the urea compound has a structure according to formula (U-2a), wherein

[0034] RP1 is selected from a hydrocarbon radical having 4 to 24 carbon atoms or a polyether segment having up to 50 oxyalkylene repeating units, preferably the segment Q-(O-AO) r , wherein Q is a C1 to C18 alkyl or alkenyl group, AO is a C2H4 or C3H6 group, and r is an integer from 2 to 35,

[0035] IC1 and IC2 are preferably selected from one of the following divalent groups ("*" indicates the connection position)

[0036]

[0037] Wherein AM is selected from the group C2H4, C3H6, C4H8, C5H 10、 C6H 12 、C6H 10 , -CH2-C6H4-CH2- or group

[0038]

[0039] Where R x and R y It represents H or CH3.

[0040] In a very preferred embodiment of (U-2a), IC1 and / or IC2 are selected from

[0041]

[0042] Even more preferably, IC1 and IC2 are selected from

[0043]

[0044] In a very preferred embodiment of (U-2a), AM is selected from C2H4 and -CH2-C6H4-CH2-.

[0045] In a very preferred embodiment of (U-2a), m is an integer from 0 to 10. In a particular embodiment, m is an integer from 1 to 5. In another embodiment, m is 0.

[0046] In another preferred embodiment, the urea compound has a structure according to formula (U-2b), wherein

[0047] Preferred embodiments of IC1 and IC2 are as described for (U-2a), in particular a C7H6 group or a -C6H4-CH2-C6H4- group,

[0048] AM1 and AM2 are selected from linear or branched, saturated or unsaturated C1 to C24 alkyl or alkenyl groups or C6H5-CH2- groups, and

[0049] RP3 is selected from hydrocarbon groups having 2 to 20 carbon atoms or polyether segments having 1 to 40 ether oxygen atoms, preferably polyether segments comprising 1 to 30 repeating units based on ethylene oxide and / or propylene oxide.

[0050] In another preferred embodiment, the urea compound has a structure according to formula (U-2c), wherein

[0051] Preferred embodiments of AM1 and AM2 are as described for (U-2b),

[0052] Preferred embodiments of AM are as described for (U-2a), and

[0053] IC4 is selected from the groups as described for IC1 and IC2 or a carbamate group-containing fragment having the structure

[0054] -[IC2-NH-(C=O)-O-RP3-O-(C=O)-NH-IC2]-

[0055] wherein IC2 is as defined for (U-2a), and RP3 is as defined for (U-2b).

[0056] For (U-2c), it is particularly preferred that IC4 is selected from the group C7H6, the group -C6H4-CH2-C6H4- and the group

[0057] -[IC2-NH-(C=O)-O-RP3-O-(C=O)-NH-IC2]-

[0058] Therein IC2 represents a C7H6 group or a -C6H4-CH2-C6H4- group, and RP3 represents a polyether fragment comprising 1 to 30 repeating units based on ethylene oxide and / or propylene oxide.

[0059] In a preferred embodiment of (U-2c), q is an integer from 0 to 15, even more preferably from 0 to 7, most preferably from 0 to 4, such as from 1 to 4.

[0060] In a preferred embodiment, at least 50% by weight of the urea compounds of the composition of the present invention have a structure according to formula (U-2a) or (U-2c).

[0061] In a very preferred embodiment, at least 50% by weight of all urea compounds of the composition of the invention have a structure according to formula (U-2a), and m is 0 or m is 1 to 5; very preferably, m is 0.

[0062] In a preferred embodiment, the urea compound is a ureaurethane, and 95-100% by weight of the urea compound contains at least one molecular fragment of the general formula (U-3a)

[0063] —O—CO—NH—Y1—NH—CO—NH—(U-3a)

[0064] in

[0065] Y1 represents a saturated or unsaturated, branched or unbranched hydrocarbon group containing 6 to 20 carbon atoms. When Y1 appears in multiple forms, Y1 independently represents a saturated or unsaturated, branched or unbranched hydrocarbon group containing 6 to 20 carbon atoms.

[0066] and in each case does not contain a molecular fragment of the general formula (U-3b)

[0067] —O—CO—NH—Y2—NH—CO—O—(U-3b)

[0068] in

[0069] Y2 represents a saturated or unsaturated, branched or unbranched hydrocarbon group containing 6 to 20 carbon atoms. When Y2 appears in multiple groups, Y2 independently represents a saturated or unsaturated, branched or unbranched hydrocarbon group containing 6 to 20 carbon atoms.

[0070] Urea compounds can be prepared in a known manner by reaction of the corresponding isocyanates with amines, for example, amines or isocyanates as described in claim 14 of WO 2015 158 407. The preparation of urea compounds of this type is described in more detail in, for example, US 7250487 B2, US 7348397 B2, EP 13 96510A1, EP 2 292 675 A1.

[0071] The synthesis of the urea compound can be suitably carried out directly in the presence of the cyclic amide and the solvent. In another embodiment, the urea compound is synthesized in the presence of the solvent and then the cyclic amide is added. In another embodiment, the urea compound is synthesized in the presence of the cyclic amide and then the solvent is added. In another embodiment, the urea compound is synthesized in the presence of the cyclic amide and a solvent and then a second solvent different from the first solvent is added.

[0072] Preferably, the urea compound has a number average molecular weight of 400 g / mol to 30000 g / mol. Preferably, the urea compound has a number average molecular weight (Mn) of at least 400 g / mol, preferably at least 500 g / mol. More preferably, the number average molecular weight is higher than 600 g / mol, even more preferably higher than 650 g / mol, most preferably higher than 800 g / mol. In addition, the number average molecular weight (Mn) of the urea compound is preferably lower than 20000 g / mol, more preferably lower than 10000 g / mol, most preferably lower than 8000 g / mol. Preferably, the number average molecular weight (Mn) is between 650 g / mol and 20000 g / mol, more preferably between 800 g / mol and 8000 g / mol, even more preferably between 800 g / mol and 5000 g / mol.

[0073] In another preferred embodiment, the number average molecular weight is at least 800 g / mol, preferably 1000 g / mol, preferably at least 1500 g / mol, preferably between 1500 g / mol and 20000 g / mol, more preferably between 1500 g / mol and 8000 g / mol, even more preferably between 1500 and 5000 g / mol.

[0074] The number-average molecular weight and weight-average molecular weight can be determined in accordance with DIN EN ISO 13885-2 (November 2021) by gel permeation chromatography (eluent: lithium bromide solution in dimethylacetamide (content 5 g / l), standard: polymethyl methacrylate, column temperature: 50° C.). Alternatively, the number-average molecular weight can be determined by calculation. In addition, for small molecules up to 1000 g / mol, the number-average molecular weight can be determined by other methods, such as mass spectrometry or nuclear magnetic resonance spectroscopy.

[0075] The composition of the present invention comprises a solvent which is different from a cyclic amide comprising at least one amide NH group, and wherein the solvent comprises at least one of an amide group and a sulfoxide group, wherein the amide nitrogen of the amide group has two substituents, wherein the substituents are selected from aliphatic and aromatic groups. The amide nitrogen of the amide group has two substituents, which means that the amide group cannot be an NH amide group.

[0076] The solvent suitably comprises at least one of N-substituted cyclic amides, acyclic dialkylamides of monofunctional and difunctional carboxylic acids, N-acylmorpholines and sulfoxides.

[0077] Suitable solvents are, for example, N-substituted cyclic amides: N-alkyllactams, preferably N-alkylbutyrolactam, N-alkylvalerolactam and N-alkylcaprolactam, wherein the alkyl group suitably has 1 to 18 carbon atoms, more preferably 1 to 12 carbon atoms, even more preferably 1 to 8 carbon atoms), and hydroxyalkyllactams (e.g. hydroxyethylpyrrolidone). Cyclic amides are amides in which the amide nitrogen and the amide carbonyl carbon are part of a cyclic structure.

[0078] Other suitable solvents are non-cyclic dialkylamides of monofunctional and difunctional carboxylic acids: N,N-dialkylamides of C1 to C18 monocarboxylic acids, bis(N,N-dialkyl)amides of C1 to C18 dicarboxylic acids; optionally, these carboxylic acids contain hydroxyl, ether or ester groups, such as N,N-dialkylamide alkyl esters, N,N-dialkylamide alkyl ethers, N,N-dialkyl lactamides. Sulfoxides are also suitable, preferably dimethyl sulfoxide. Non-cyclic amides are amides in which both the amide nitrogen and the amide carbonyl carbon are not part of a cyclic structure. According to this definition, for example, N-formylmorpholine is considered to be a non-cyclic amide.

[0079] Other suitable solvents are the non-cyclic amides obtainable from the reaction of diamines and monocarboxylic acids. Suitable examples are the reaction products of C1 to C18 monocarboxylic acids and C2 to C12 alkylenediamines.

[0080] Suitable examples of N-alkylbutyrolactams are N-methylbutyrolactam, N-ethylbutyrolactam, N-butylbutyrolactam, N-octylbutyrolactam and N-hydroxyethylbutyrolactam. Suitable examples of N-substituted caprolactams are N-ethylcaprolactam, N-methylcaprolactam, N-butylcaprolactam, N-propylcaprolactam.

[0081] Suitable solvents are also linear amides, for example N,N-dimethylformamide, N,N-dimethylacetamide, N,N-dimethylamides of C3 to C18 monocarboxylic acids (preferably N,N-dimethylamides of C6 to C10 monocarboxylic acids), N,N-dialkylamide alkyl esters, N,N-dialkylamide alkyl ethers and acylmorpholines.

[0082] Preferred examples of these solvents are also N,N-dimethylamide alkyl esters, N,N-dimethylamide alkyl ethers, N-formylmorpholine and N-acetylmorpholine.

[0083] Another suitable solvent is N-acetyl caprolactam.

[0084] Preferably, the solvent is liquid at 23°C and 1013 mbar.

[0085] The composition of the present invention comprises a cyclic amide comprising at least one amide NH group.A cyclic amide is an amide in which the amide nitrogen and the amide carbonyl carbon are part of a cyclic structure.

[0086] The cyclic amide suitably comprises a maximum of 2 amide groups. In another embodiment, the cyclic amide suitably comprises two amide groups, while in an even different embodiment, the cyclic amide comprises exactly one amide group.

[0087] Preferably, the cyclic amide consists of C, H, O and N atoms. This means that the cyclic amide consists only of these atoms, without any other atoms not mentioned being present.

[0088] Suitably, the cyclic amide is a lactam. A lactam is a cyclic amide with an amide group. Preferably, the cyclic amide comprises at least one of ε-caprolactam, γ-butyrolactam, δ-valerolactam and mixtures thereof.

[0089] Furthermore, cyclic amides are suitable in which one or more of the carbon atoms which are part of the ring carry substituents, preferably aliphatic substituents.

[0090] The molecular weight of the cyclic amide is preferably 71 to 250 g / mol. The molecular weight of the cyclic amide is more preferably 85 to 220 g / mol. The molecular weight of the cyclic amide is more preferably 85 to 198 g / mol, and the molecular weight of the cyclic amide is most preferably 85 to 145 g / mol, such as 99 to 130 g / mol or 99 to 115 g / mol.

[0091] The weight ratio of cyclic amide and solvent in the composition is preferably 0.5:99.5 to 60.0:40.0. More preferably, the weight ratio is 0.7:99.3 to 55.0:45.0; even more preferably 1.0:99.0 to 50.0:50.0; most preferably 2.0:98.0 to 45:55; in a further embodiment, the cyclic amide and solvent are preferably present in the composition in a weight ratio of 5.0:95.0 to 40.0:60.0, more preferably 10:90 to 37.5:62.5.

[0092] Preferably, the amount of cyclic amide is at least 0.7%, preferably at least 1.0%, more preferably at least 2.0%, even more preferably at least 5.0%, most preferably at least 10.0%, such as at least 20.0% or at least 25.0%, compared to the total weight of cyclic amide and solvent. Also preferably, the amount of cyclic amide is at most 55.0%, preferably at most 50.0%, more preferably at most 45.0%, such as at most 40.0% or at most 37.5%, relative to the total weight of cyclic amide and solvent.

[0093] Typically, the composition is liquid at 23°C and 1013 mbar.

[0094] The composition suitably comprises from 0.1 to 15.0 wt% of the salt, calculated on the combined weight of the cyclic amide, at least one solvent, the urea compound and the salt.

[0095] Typically, the composition may comprise one or more salts. The salts according to the invention contain cations of elements of the main groups I and II of the periodic table (alkali metals and alkaline earth metals) or ammonium ions (including substituted ammonium ions, such as alkylammonium ions) and mixtures thereof. Preferred salts are salts containing lithium, calcium or magnesium, particularly preferably lithium and calcium cations, preferably in the form of chlorides, acetates and / or nitrates. In some embodiments, the anions contained in the salts are preferably monovalent anions, particularly preferably halides, pseudohalides, formates, acetates and / or nitrates, most particularly preferably chlorides, acetates and / or nitrates.

[0096] Particularly preferred salts are inorganic lithium salts, such as lithium chloride or lithium nitrate, and ammonium salts, such as alkylammonium salts, in particular quaternary ammonium salts, such as tetraalkylammonium halides.

[0097] The composition suitably comprises 0.1 to 15.0 wt% of the salt, wherein the wt% is calculated based on the weight of the cyclic amide, the solvent, the urea compound and the salt. Preferably, the composition comprises the salt in an amount of 0.1 to 10.0 wt%, more preferably 0.1 to 8.0 wt%, even more preferably 0.1 to 5.0 wt%, and most preferably 0.1 to 3.0 wt%.

[0098] In a preferred embodiment, the composition does not contain a salt selected from lithium salts and halide salts or contains such salts in a low amount. A low amount is an amount of salt not exceeding 1.0 wt %, more preferably, the amount not exceeding 0.5 wt %, more preferably, the amount not exceeding 0.3 wt %, preferably, not exceeding 0.1 wt %, calculated on the weight of the composition.

[0099] In another preferred embodiment, the composition does not contain salt. If the composition does not contain salt, preferably the salt content does not exceed 0.50 wt%, more preferably does not exceed 0.30 wt%, preferably does not exceed 0.10 wt%, for example does not exceed 0.05 wt%, calculated on the weight of the composition.

[0100] In some embodiments, the composition further comprises a surfactant. The salt in the preferred composition can be replaced by a surfactant. The surfactant can preferably completely replace the salt, or can be added in addition to the salt. In the latter case, the surfactant can partially replace the salt, which results in a reduced salt content, or a surfactant can be added in addition to the salt, and the salt content remains unreduced. Suitable surfactants are anionic surfactants, such as sulfosuccinates, alkyl (alkenyl) sulfates, alkyl (alkenyl) ether sulfates, ester sulfonates, soaps, ether carboxylic acids; nonionic surfactants, such as alcohol alkoxylates, alkyl glycosides, fatty acid ester alkoxylates, amine oxides, gemini surfactants; cationic surfactants, such as tetraalkylammonium salts, quaternary ammonium salts, esterquats; amphoteric or zwitterionic surfactants, such as betaines, alkylamide betaines, imidazolines. Particularly preferred are quaternary ammonium salts and sulfosuccinates. Suitably, the surfactant is used in an amount of 0.1 to 15.0 wt%, preferably 0.2 to 14.0 wt%, more preferably 0.4 to 13.0 wt%, even more preferably 0.5 to 12.0 wt%, most preferably 0.8 to 11.0 wt%, for example 1.0 to 10.0 wt%, calculated on the total weight of the composition.

[0101] Preferably, the composition comprises

[0102] 1 to 60% by weight of a cyclic amide comprising at least one amide NH group,

[0103] 5 to 70 wt. % of a solvent other than a cyclic amide comprising at least one amide NH group, and wherein the solvent comprises at least one of a dialiphatic substituted amide group and a sulfoxide group,

[0104] 5 to 60% by weight of a urea compound having a number average molecular weight of at least 350 g / mol,

[0105] It is calculated based on the total weight of the cyclic amide, solvent and urea compound.

[0106] In a particularly preferred embodiment, the composition comprises

[0107] 2 to 55% by weight of a cyclic amide comprising at least one amide NH group,

[0108] 10-65 wt. % of a solvent other than a cyclic amide comprising at least one amide NH group, and wherein the solvent comprises at least one of a dialiphatic substituted amide group and a sulfoxide group,

[0109] 10-55% by weight of a urea compound having a number average molecular weight of at least 350 g / mol,

[0110] It is calculated based on the total weight of the cyclic amide, solvent and urea compound.

[0111] In a more preferred embodiment, the composition comprises

[0112] 5 to 50% by weight of a cyclic amide comprising at least one amide NH group,

[0113] 15-60 wt. % of a solvent, the solvent being different from a cyclic amide comprising at least one amide NH group, and wherein the solvent comprises at least one of a dialiphatic substituted amide group and a sulfoxide group,

[0114] 15-50 wt. % of a urea compound having a number average molecular weight of at least 350 g / mol,

[0115] It is calculated based on the total weight of the cyclic amide, solvent and urea compound.

[0116] In a more preferred embodiment, the composition comprises

[0117] 10 to 45% by weight of a cyclic amide comprising at least one amide NH group,

[0118] 20-55 wt. % of a solvent other than a cyclic amide comprising at least one amide NH group, and wherein the solvent comprises at least one of a dialiphatic substituted amide group and a sulfoxide group,

[0119] 16-45 wt. % of a urea compound having a number average molecular weight of at least 350 g / mol,

[0120] It is calculated based on the total weight of the cyclic amide, solvent and urea compound.

[0121] In another preferred embodiment, the composition comprises

[0122] 10 to 45% by weight of a cyclic amide comprising at least one amide NH group,

[0123] 25-50 wt. % of a solvent other than a cyclic amide comprising at least one amide NH group, and wherein the solvent comprises at least one of a dialiphatic substituted amide group and a sulfoxide group,

[0124] 17-40 wt. % of a urea compound having a number average molecular weight of at least 350 g / mol,

[0125] It is calculated based on the total weight of the cyclic amide, solvent and urea compound.

[0126] In a very preferred embodiment, the composition comprises

[0127] 15 to 40% by weight of a cyclic amide comprising at least one amide NH group,

[0128] 25-50 wt. % of a solvent other than a cyclic amide comprising at least one amide NH group, and wherein the solvent comprises at least one of a dialiphatic substituted amide group and a sulfoxide group,

[0129] 18-38 wt. % of a urea compound having a number average molecular weight of at least 350 g / mol,

[0130] It is calculated based on the total weight of the cyclic amide, solvent and urea compound.

[0131] In another preferred embodiment, the composition comprises

[0132] 15-25% by weight of a cyclic amide comprising at least one amide NH group,

[0133] 25-50 wt. % of a solvent other than a cyclic amide comprising at least one amide NH group, and wherein the solvent comprises at least one of a dialiphatic substituted amide group and a sulfoxide group,

[0134] 19-35% by weight of a urea compound having a number average molecular weight of at least 350 g / mol,

[0135] It is calculated based on the total weight of the cyclic amide, solvent and urea compound.

[0136] In yet another preferred embodiment, the composition comprises

[0137] 15-20% by weight of a cyclic amide comprising at least one amide NH group,

[0138] 30-50 wt. % of a solvent other than a cyclic amide comprising at least one amide NH group, and wherein the solvent comprises at least one of a dialiphatic substituted amide group and a sulfoxide group,

[0139] 20-33% by weight of a urea compound having a number average molecular weight of at least 350 g / mol,

[0140] It is calculated based on the total weight of the cyclic amide, solvent and urea compound.

[0141] In a particular embodiment, the composition comprises at least two solvents that are different from each other, provided that one of the solvents is dimethyl sulfoxide (DMSO) and the second solvent is a solvent comprising at least one dialiphatic substituted amide group. Preferably, the weight of DMSO is at least 1%, preferably at least 2%, more preferably at least 5%, even more preferably at least 7%, most preferably at least 10% relative to the total weight of DMSO, the second solvent comprising at least one dialiphatic substituted amide group and the cyclic amide comprising at least one amide NH group. Also preferably, the weight of DMSO is at most 60%, preferably at most 50%, more preferably at most 45%, even more preferably at most 40%, most preferably at most 35%, for example at most 30% relative to the total weight of DMSO, the second solvent comprising at least one dialiphatic substituted amide group and the cyclic amide comprising at least one amide NH group.

[0142] Furthermore, the present invention relates to the use of the composition for controlling the rheology of a liquid composition.The term "liquid composition" in the present invention means a composition which is liquid at 23°C and 1013 mbar.

[0143] The composition of the present invention can be used to control the rheology of various liquid compositions. Therefore, in one embodiment, the liquid composition can be an aqueous composition. The main or even the only liquid diluent of the liquid aqueous composition is water. In addition, the aqueous composition can contain a certain amount of organic diluent. The organic diluent is the same or different from the at least one solvent, the solvent is different from the cyclic amide containing at least one amide NH group, and wherein the solvent contains at least one of an amide group and a sulfoxide group, wherein the amide nitrogen of the amide group has two substituents, wherein the substituents are selected from aliphatic and aromatic groups. Preferably, the liquid aqueous composition contains less than 35% by weight, preferably less than 25% by weight, more preferably less than 20% by weight, most preferably less than 10% by weight or even less than 5% by weight of organic diluent, calculated by the total weight of the liquid composition. In a special embodiment, the liquid aqueous composition does not contain an organic diluent at all.

[0144] Typically, the liquid aqueous composition comprises at least 10 % by weight, preferably at least 15 % by weight, more preferably at least 20 % by weight of water. In some cases, the liquid aqueous composition may comprise at least 25 % by weight, more preferably at least 30 % by weight of water. Typically, the liquid aqueous composition comprises at most 90 % by weight of water, for example at most 80 % by weight or at most 70 % by weight. In a particular embodiment, the liquid aqueous composition comprises at most 95 % by weight, even at most 97, 98 or 99 % by weight of water.

[0145] In another embodiment, the liquid composition can be a non-aqueous composition. The non-aqueous composition is substantially free of water. This means that the liquid composition suitably contains 0.0 to less than 10.0 wt % water, preferably 0.0 to 7.0 wt % water, calculated by the total weight of the liquid composition. More preferably, the non-aqueous liquid composition contains less than 5.0 wt % water. For example, the liquid composition contains less than 3.0 wt % or less than 1.0 wt % water, calculated by the total weight of the liquid composition.

[0146] Suitably, the liquid composition is selected from coating compositions, clearcoat compositions, lacquers, varnishes, plastic preparations, pigment pastes, effect pigment pastes, polymer preparations, sealant preparations, cosmetic preparations, home care or industrial care preparations (including perfume and fragrance preparations), ceramic preparations, adhesive preparations, liquid preparations for gas and oil production, compositions for the manufacture of electrical components and circuits, liquid preparations for energy storage media, cleaners, potting compounds, building material preparations, lubricants, filling compounds, wax emulsions, metalworking fluids, metalworking products, liquid compositions in the form of sprays, so-called deposition aids (e.g. for plant protection agents or for the general purpose of reducing drift), inks, printing inks and inkjet inks or compositions which can be used as corrosion protection in the field of marine and protective coatings, and mixtures thereof.

[0147] Other liquid compositions in which the composition of the invention can be used are solvent-borne or solvent-free coatings, printing inks and inks and lacquers, for example for plastic varnishes, wire enamels, floor coatings, coating compositions for coating foods and seeds and so-called color resists, which are used for color filters, for example in flat panel displays such as liquid crystal displays. The application fields of lacquers also include pasty materials, which usually have a very high solids ratio and a small proportion of liquid components, such as so-called pigment pastes or pastes based on effect pigments, for example metallic effect pigments, for example aluminum pigments, silver pigments, brass pigments, zinc pigments, copper pigments, bronze pigments such as gold bronze, fire-dyed bronze or iron oxide aluminum pigments. Effect pigments also include, for example, interference pigments or pearlescent pigments, for example metal oxide mica pigments, fish silver, bismuth oxide chloride or basic lead carbonate.

[0148] Plastic preparations can be liquid or non-liquid starting materials to produce plastic materials, which are preferably converted into duromers by a chemical crosslinking process ("curing"). Preferred plastic preparations are unsaturated polyester resins, vinyl ester resins, acrylate resins, epoxy resins, polyurethane resins, formaldehyde resins (e.g. melamine-formaldehyde or urea-formaldehyde resins). These can be cured under very different conditions, for example at room temperature (cold curing systems) or at elevated temperatures (hot curing systems), optionally with the application of pressure ("closed mold" applications, sheet molding compounds or block molding compounds). Plastic preparations also include PVC plastisols.

[0149] Cosmetic preparations can be various liquid compositions which are used in the so-called personal care or healthcare sector, for example lotions, creams, pastes (e.g. toothpaste), foams (e.g. shaving foam), gels (e.g. shaving gel), shower gels or active ingredients in gel preparations, shampoos, liquid soaps, nail polishes, lipsticks and hair dyes.

[0150] So-called wax emulsions are preferably solid waxes dispersed in the form of particles in water or an organic medium at room temperature.

[0151] Building material preparations can be liquid or pasty materials that are used in the construction sector and set after curing. Examples are hydraulic binders, such as concrete, cement, mortar, tile adhesives and plasters.

[0152] Metalworking fluids can be cutting fluids, drilling fluids (e.g. drilling fluids for metalworking) or forging fluids or general lubricants. Other potential areas include mold release agents (usually in the form of aqueous emulsions, such as aluminum die casting and foundry applications), foundry cleaning agents (casting coatings) and metal finishing liquids (e.g. "surface finishing", surface treatment and electroplating).

[0153] Lubricants are means for lubrication, ie for reducing friction and wear, as well as providing power, cooling, vibration damping, sealing and corrosion protection; liquid lubricants are preferred.

[0154] Cleaning agents are used to clean various articles, for example in the field of home care or industrial care. They remove or help remove impurities, residues and deposits. Cleaning agents also include detergents (mainly for cleaning textiles, their precursors, leather and tableware) and personal care products. Preparations containing perfumes and other fragrances (as liquid raw materials or in capsule form), such as perfume gels, also belong to this application field.

[0155] Liquid preparations for gas and oil production are preparations used to develop and exploit mineral deposits. Drilling fluids or "drilling muds" are preferred examples. Another application example is liquids used to prepare or perform hydraulic fracturing processes and liquids that support gas and oil production processes.

[0156] Adhesives are all bonding materials that are liquid under processing conditions and can connect parts by both surface bonding and internal strength.

[0157] Liquid composition of the present invention can also comprise conventional additives.The example of additive has antiblocking agent, stabilizer, antioxidant, pigment, wetting agent, dispersant, emulsifying agent, additional rheological additive, ultraviolet light absorber, free radical scavenger, smooth additive, defoamer, adhesion promoter, leveling agent, wax, nanoparticle, film-forming aid and flame retardant.Preferred additive is wetting agent, dispersant and / or emulsifying agent and rheological additive, and they are different from composition of the present invention, for example based on clay thickener (comprising organoclay), (poly) amide, polysaccharide (such as cellulose derivative, guar gum, xanthan gum), polyacrylate or associative thickener.In an example, composition of the present invention can be used in combination with other thickeners of low, medium and / or high shear performance that influence the liquid composition that needs to be modified aspect its rheological behavior.

[0158] In another embodiment, the present invention also relates to a method for controlling the rheology of a liquid composition, comprising the steps of providing a composition according to the present invention, providing a liquid composition and mixing the composition according to the present invention and the liquid composition. Suitable liquid compositions are the above-mentioned liquid compositions and the like. The step of mixing the components can be performed according to current methods known to those skilled in the art. This may involve mixing by manual or electric means. Mixing is combining the compositions and applying shear forces to the combined compositions.

[0159] The present invention further relates to a liquid composition comprising a composition according to the present invention and an adhesive. Suitable adhesives include at least one of alkyd resins (e.g., short oil, medium oil, or long oil alkyd resins), unsaturated polyester resins, vinyl ester resins, acrylate resins, epoxy resins, polyurethane resins, polyaspartic acid resins, phenolic resin adhesives, silicone resins, chlorinated rubber, vinyl-based adhesives, polyvinyl alcohol, polyvinyl acetate, saturated polyester adhesives, polyacrylates and acrylate copolymers, urea and melamine resins, silicate adhesives, cellulose-based adhesives, and silyl-modified polymers. Preferred adhesives include at least one of alkyd resins (e.g., short oil, medium oil, or long oil alkyd resins), unsaturated polyester resins, vinyl ester resins, acrylate resins, epoxy resins, polyurethane resins, polyacrylates and acrylate copolymers, polyaspartic acid resins, and silyl-modified polymers.

[0160] These adhesives can preferably be solvent-based, solvent-free or water-based adhesives. Solvent-based and water-based adhesives can be provided in the form of solutions, emulsions or dispersions. Therefore, the above-mentioned adhesives also include water-based adhesive systems, such as styrene-acrylic dispersions, urethane-acrylic dispersions and alkyd emulsions. Adhesives also include non-aqueous dispersion (NAD) systems.

[0161] Another object of the present invention is to provide an article, wherein at least a portion of the article surface is coated with a liquid composition. In different embodiments, the coated article can be obtained by the following steps: providing an article, providing a liquid composition according to the present invention, and coating at least a portion of the article surface with the liquid composition.

[0162] Furthermore, in an even different embodiment, the present invention relates to a coated article, wherein at least a portion of the surface of the article is coated with a liquid composition according to the present invention, and wherein the liquid composition is hardened. In another embodiment, the coated article can be obtained by the steps of providing an article, providing a liquid composition according to the present invention, coating at least a portion of the surface of the article with the liquid composition, and hardening the liquid composition.

[0163] Suitable articles are all three-dimensional objects, regardless of their size and volume, and regardless of whether they are mobile or immobile. Exemplary but non-limiting examples are building interiors and exteriors, floors, furniture, vehicles for transportation (such as cars, bicycles, ships, airplanes, agricultural machinery and all types of freight vehicles), bridges and tunnels, machinery and production equipment, electrical equipment, cans, metal coils, wires, containers, household products and hardware, pulp and paper, and all types of articles made of wood, metal, plastic or glass (for example, for functional or decorative purposes). The meaning of the term "coating" is well known to those skilled in the art. In this article, it involves applying a liquid composition to the surface or other area of ​​the article to at least partially cover it or even completely wrap the article. In this case, the liquid composition becomes tough or hardened after being applied to the article. Hardening refers to converting the liquid composition into a solid state. This can be achieved by evaporating a liquid diluent (physical drying) or by a chemical cross-linking reaction (curing) and a combination thereof.

[0164] The invention will be further illustrated below with reference to the examples. The selection of corresponding reaction conditions, such as reaction temperature, reaction time and dosage rate, is known to the person skilled in the art and is described in more detail in the working examples.

[0165] Experimental Section

[0166] Embodiments of the invention

[0167] Preparation of intermediates

[0168] Table 1: Abbreviations

[0169]

[0170]

[0171] Preparation of intermediates I1 to I6:

[0172] Table 2: Intermediates

[0173] Intermediates Monohydric alcohol Diisocyanates I1 Butyl triglycol TDI T65 I2 Polyethylene glycol monomethyl ether (hydroxyl value: 125 mg KOH / g) TDI T80 I3 (Z)-Octadeca-9-enol TDI T65 I4 Polyethylene glycol monobutyl ether (hydroxyl value: 148 mg KOH / g) TDI T65 I5 Polyethylene glycol monobutyl ether (hydroxyl value: 183 mg KOH / g) TDI T65 I6 Butyl triglycol TDI T80

[0174] The hydroxyl value is determined by acetylation of the free hydroxyl groups of the substance with acetic anhydride in pyridine solvent. After the reaction is complete, water is added to convert the remaining unreacted acetic anhydride into acetic acid, which is measured by titration with potassium hydroxide.

[0175] Procedure for intermediates I1 to I6:

[0176] 2 mol of TDI T65 or TDI T80 and 200 ppm of benzoyl chloride were weighed separately, placed in a glass flask equipped with a stirrer, a reflux condenser and a nitrogen inlet, and heated to 40° C. Subsequently, 1 mol of monohydric alcohol (according to Table 2 above) was added dropwise to the reaction mixture over 30 minutes. The reaction mixture was stirred at 60° C. for another 5 hours. A transparent, light yellow liquid intermediate containing an excess of diisocyanate was obtained. The excess diisocyanate contained in the intermediate was removed by distillation, thereby obtaining intermediates I1 to I6.

[0177] Comparative Example (not the present invention)

[0178] C1:

[0179] In a four-necked flask with a stirrer, 75.0 g of N-butylbutyrolactam was heated to 80° C. under stirring under a nitrogen atmosphere. 3.61 g of m-xylylenediamine (26.5 mmol) was added and the mixture was homogenized. 21.4 g of intermediate I1 (53.0 mmol) was added dropwise over 30 minutes under stirring so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. A transparent light yellow product was obtained as a result.

[0180] C2:

[0181] In a four-necked flask with a stirrer, 1.06 g of lithium chloride was added to 73.9 g of N-butylbutyrolactam under stirring. The mixture was heated to 80° C. under a nitrogen atmosphere. The lithium chloride dissolved within 30 minutes under stirring. 3.61 g of m-phenylenediamine (26.5 mmol) was added and the mixture was homogenized. 21.4 g of intermediate I1 (53.0 mmol) was added dropwise within 30 minutes under stirring, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. The result was a transparent light yellow product.

[0182] C3:

[0183] In a four-necked flask with a stirrer, 70.0 g of N-butylbutyrolactam was heated to 80° C. under stirring under a nitrogen atmosphere. 4.33 g of m-xylylenediamine (31.8 mmol) was added and the mixture was homogenized. Under stirring, 25.7 g of intermediate I1 (63.6 mmol) was added dropwise over 30 minutes, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. A transparent light yellow product was obtained as a result.

[0184] C4:

[0185] In a four-necked flask with a stirrer, 1.27 g of lithium chloride was added to 68.7 g of N-butyl butyrolactam under stirring. The mixture was heated to 80° C. under a nitrogen atmosphere. The lithium chloride was dissolved within 30 minutes under stirring. 4.33 g of m-phenylenediamine (31.8 mmol) was added and the mixture was homogenized. Under stirring, 25.7 g of intermediate I1 (63.6 mmol) was added dropwise within 30 minutes so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. The result was a transparent light yellow product.

[0186] C5:

[0187] In a four-necked flask with a stirrer, 70.0 g of N-butyl butyrolactam was heated to 80° C. under a nitrogen atmosphere. Under stirring, 3.20 g of m-xylylenediamine (23.5 mmol) was added and the mixture was homogenized. Under stirring, 26.8 g of intermediate I4 (47.0 mmol) was added dropwise over 30 minutes, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. As a result, a transparent light yellow product was obtained.

[0188] C6:

[0189] In a four-necked flask with a stirrer, 75.0 g of N-butylbutyrolactam was heated to 80° C. under a nitrogen atmosphere. Under stirring, 4.21 g of m-xylylenediamine (30.9 mmol) was added and the mixture was homogenized. Under stirring, 30.8 g of intermediate I5 (61.8 mmol) was added dropwise over 30 minutes, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. A transparent light yellow product was obtained as a result.

[0190] C7:

[0191] In a four-necked flask with a stirrer, 1.25 g of lithium chloride was added to 63.8 g of N-butyl butyrolactam under stirring. The mixture was heated to 80 ° C under a nitrogen atmosphere. Under stirring, the lithium chloride was dissolved within 30 minutes. Under stirring, 4.21 g of m-phenylenediamine (30.9 mmol) was added, and the mixture was homogenized. Under stirring, 30.8 g of intermediate I5 (61.8 mmol) was added dropwise within 30 minutes, so that the temperature did not exceed 85 ° C. Subsequently, the mixture was stirred at 80 ° C for 3 hours. The result was a transparent light yellow product.

[0192] C8:

[0193] In a four-necked flask with a stirrer, 65.0 g of N-butyl butyrolactam was heated to 80° C. under stirring under a nitrogen atmosphere. 3.92 g of m-xylylenediamine (28.8 mmol) was added and the mixture was homogenized. Over 30 minutes, a mixture of 7.47 g of intermediate I1 (18.5 mmol) and 23.6 g of intermediate I2 (38.8 mmol) was added dropwise under stirring so that the temperature did not exceed 85° C. Subsequently, the mixture was stirred at 80° C. for 3 hours. A transparent light yellow product was obtained as a result.

[0194] C9:

[0195] In a four-necked flask with a stirrer, 1.00 g of lithium chloride was added to 64.0 g of N-butyl butyrolactam under stirring. The mixture was heated to 80° C. under a nitrogen atmosphere. The lithium chloride dissolved within 30 minutes under stirring. 3.92 g of m-phenylenediamine (28.8 mmol) was added and the mixture was homogenized. Under stirring, a mixture of 7.47 g of intermediate I1 (18.5 mmol) and 23.6 g of intermediate I2 (38.8 mmol) was added dropwise within 30 minutes so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. The result was a transparent light yellow product.

[0196] C10:

[0197] In a four-necked flask with a stirrer, 65.0 g of N-butyl butyrolactam was heated to 80° C. under a nitrogen atmosphere. Under stirring, 3.92 g of m-xylylenediamine (28.8 mmol) was added and the mixture was homogenized. Under stirring, a mixture of 7.47 g of intermediate I6 (18.5 mmol) and 23.6 g of intermediate I2 (38.8 mmol) was added dropwise over 30 minutes so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. A transparent light yellow product was obtained.

[0198] C11:

[0199] In a four-necked flask with a stirrer, 60.0 g of N-butyl butyrolactam was heated to 80° C. under a nitrogen atmosphere. 4.48 g of m-xylylenediamine (32.9 mmol) was added under stirring and the mixture was homogenized. A mixture of 8.54 g of intermediate I6 (21.4 mmol) and 27.0 g of intermediate I2 (44.4 mmol) was added dropwise over 30 minutes, with the temperature not exceeding 85° C. during stirring. The mixture was then stirred at 80° C. for 3 hours. A transparent light yellow product was obtained as a result.

[0200] C12:

[0201] In a glass flask equipped with a stirrer, a reflux condenser and a nitrogen inlet, 85.0 g of N-butyl butyrolactam was heated to 60 ° C under stirring. Subsequently, 1.17 g of 1,3-diaminopropane (15.8 mmol) was added and briefly homogenized. A homogeneous mixture of 13.7 g of intermediate I3 (30.0 mmol) and 0.126 g of hexamethylene diisocyanate (0.751 mmol) was added dropwise to the reaction mixture over 25 minutes. The reaction mixture was stirred at 80 ° C for another 3 hours. As a result, a transparent yellow liquid product was obtained.

[0202] C13:

[0203] In a glass flask equipped with a stirrer, a reflux condenser and a nitrogen inlet, 1.36 g of lithium chloride was dissolved in 83.6 g of N-butyl butyrolactam and stirred at 60 ° C for 30 minutes to obtain a clear solution. Subsequently, 1.17 g of 1,3-diaminopropane (15.8 mmol) was added and briefly homogenized. Within 25 minutes, a uniform mixture of 13.7 g of intermediate I3 (30.0 mmol) and 0.126 g of hexamethylene diisocyanate (0.751 mmol) was added dropwise to the reaction mixture. The reaction mixture was stirred at 80 ° C for another 3 hours. As a result, a transparent yellow liquid product was obtained.

[0204] C14:

[0205] In a four-necked flask with a stirrer, 1.25 g of lithium chloride was added to 53.8 g of N-butyl butyrolactam under stirring. The mixture was heated to 80° C. under a nitrogen atmosphere. The lithium chloride dissolved within 30 minutes under stirring. 6.49 g of m-phenylenediamine (47.7 mmol) was added and the mixture was homogenized. Under stirring, 38.5 g of intermediate I1 (95.4 mmol) was added dropwise within 30 minutes, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. The result was a transparent light yellow product.

[0206] C15:

[0207] In a four-necked flask with a stirrer, 75.0 g of N-methylcaprolactam was heated to 80° C. under nitrogen atmosphere with stirring. 3.61 g of m-xylylenediamine (26.5 mmol) was added and the mixture was homogenized. Under stirring, 21.4 g of intermediate I1 (53.0 mmol) was added dropwise over 30 minutes, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. As a result, a transparent light yellow product was obtained.

[0208] C16:

[0209] In a four-necked flask with a stirrer, 70.0 g of N-methylcaprolactam was heated to 80° C. under stirring under a nitrogen atmosphere. 4.33 g of m-xylylenediamine (31.8 mmol) was added and the mixture was homogenized. Under stirring, 25.7 g of intermediate I1 (63.6 mmol) was added dropwise over 30 minutes, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. As a result, a transparent light yellow product was obtained.

[0210] C17:

[0211] In a four-necked flask with a stirrer, 75.0 g of N-ethyl caprolactam was heated to 80° C. under stirring under a nitrogen atmosphere. 3.61 g of m-xylylenediamine (26.5 mmol) was added and the mixture was homogenized. 21.4 g of intermediate I1 (53.0 mmol) was added dropwise over 30 minutes under stirring, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. A transparent light yellow product was obtained as a result.

[0212] C18:

[0213] In a four-necked flask with a stirrer, 70.0 g of N-ethyl caprolactam was heated to 80° C. under stirring under a nitrogen atmosphere. 4.33 g of m-xylylenediamine (31.8 mmol) was added and the mixture was homogenized. 25.7 g of intermediate I1 (63.6 mmol) was added dropwise over 30 minutes under stirring, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. A transparent light yellow product was obtained as a result.

[0214] C19:

[0215] In a four-necked flask with a stirrer, 75.0 g of N-cyclohexylpyrrolidone was heated to 80° C. under stirring under a nitrogen atmosphere. 3.61 g of m-xylenediamine (26.5 mmol) was added and the mixture was homogenized. 21.4 g of intermediate I1 (53.0 mmol) was added dropwise over 30 minutes under stirring so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. A transparent light yellow product was obtained as a result.

[0216] C20:

[0217] In a four-necked flask with a stirrer, 70.0 g of N-cyclohexylpyrrolidone was heated to 80° C. under stirring under a nitrogen atmosphere. 4.33 g of m-xylenediamine (31.8 mmol) was added and the mixture was homogenized. 25.7 g of intermediate I1 (63.6 mmol) was added dropwise under stirring over 30 minutes, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. A transparent light yellow product was obtained as a result.

[0218] Embodiments of the present invention

[0219] E1:

[0220] In a four-necked flask with a stirrer, 30.0 g of ε-caprolactam was added to 45.0 g of N-butylbutyrolactam under stirring. The mixture was heated to 80° C. under a nitrogen atmosphere. The ε-caprolactam dissolved within 30 minutes under stirring. 3.61 g of m-phenylenediamine (26.5 mmol) was added and the mixture was homogenized. 21.4 g of intermediate I1 (53.0 mmol) was added dropwise within 30 minutes under stirring, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. A transparent light yellow product was obtained as a result.

[0221] E2:

[0222] In a four-necked flask with a stirrer, 28.0 g of ε-caprolactam was added to 21.0 g of N-butyl butyrolactam and 21.0 g of DMSO under stirring. The mixture was heated to 80° C. under a nitrogen atmosphere. The ε-caprolactam dissolved within 30 minutes under stirring. 4.33 g of m-phenylenediamine (31.8 mmol) was added to homogenize the mixture. Under stirring, 25.7 g of intermediate I1 (63.6 mmol) was added dropwise within 30 minutes, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. The result was a transparent light yellow product.

[0223] E3:

[0224] In a four-necked flask with a stirrer, 28.0 g of ε-caprolactam was added to 28.0 g of N-butyl butyrolactam and 14 g of DMSO under stirring. The mixture was heated to 80° C. under a nitrogen atmosphere. Under stirring, the ε-caprolactam was dissolved within 30 minutes. 4.33 g of m-phenylenediamine (31.8 mmol) was added and the mixture was homogenized. Under stirring, 25.7 g of intermediate I1 (63.6 mmol) was added dropwise within 30 minutes, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. The result was a transparent light yellow product.

[0225] E4:

[0226] In a four-necked flask with a stirrer, 28.0 g of ε-caprolactam was added to 42.0 g of N-butyl butyrolactam under stirring. The mixture was heated to 80° C. under a nitrogen atmosphere. Under stirring, the ε-caprolactam was dissolved within 30 minutes. 3.20 g of m-phenylenediamine (23.5 mmol) was added and the mixture was homogenized. Under stirring, 26.8 g of intermediate I4 (47.0 mmol) was added dropwise within 30 minutes, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. The result was a transparent light yellow product.

[0227] E5:

[0228] In a four-necked flask with a stirrer, 28.0 g of ε-caprolactam was added to 28.0 g of N-butyl butyrolactam and 14.0 g of DMSO under stirring. The mixture was heated to 80° C. under a nitrogen atmosphere. Under stirring, the ε-caprolactam dissolved within 30 minutes. 3.20 g of m-phenylenediamine (23.5 mmol) was added and the mixture was homogenized. Under stirring, 26.8 g of intermediate I4 (47.0 mmol) was added dropwise within 30 minutes, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. The result was a transparent light yellow product.

[0229] E6:

[0230] In a four-necked flask with a stirrer, 26.0 g of ε-caprolactam was added to 39.0 g of N-butylbutyrolactam under stirring. The mixture was heated to 80° C. under a nitrogen atmosphere. Under stirring, the ε-caprolactam dissolved within 30 minutes. 4.21 g of m-phenylenediamine (30.9 mmol) was added and the mixture was homogenized. Under stirring, 30.8 g of intermediate I5 (61.8 mmol) was added dropwise within 30 minutes, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. The result was a transparent light yellow product.

[0231] E7:

[0232] In a four-necked flask with a stirrer, 26.0 g of ε-caprolactam was added to 39.0 g of N-butyl butyrolactam under stirring. The mixture was heated to 80° C. under a nitrogen atmosphere. Under stirring, the ε-caprolactam dissolved within 30 minutes. 3.92 g of m-phenylenediamine (28.8 mmol) was added and the mixture was homogenized. Under stirring, a mixture of 7.47 g of intermediate I1 (18.5 mmol) and 23.6 g of intermediate I2 (38.8 mmol) was added dropwise within 30 minutes, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. The result was a transparent light yellow product.

[0233] E8:

[0234] In a four-necked flask with a stirrer, 26.0 g of ε-caprolactam was added to 39.0 g of N-butyl butyrolactam under stirring. The mixture was heated to 80° C. under a nitrogen atmosphere. Under stirring, the ε-caprolactam dissolved within 30 minutes. 3.92 g of m-phenylenediamine (28.8 mmol) was added and the mixture was homogenized. Under stirring, a mixture of 7.47 g of intermediate I6 (18.5 mmol) and 23.6 g of intermediate I2 (38.8 mmol) was added dropwise within 30 minutes so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. The result was a transparent light yellow product.

[0235] E9:

[0236] In a four-necked flask with a stirrer, 24.0 g of ε-caprolactam was added to 36.0 g of N-butyl butyrolactam under stirring. The mixture was heated to 80° C. under a nitrogen atmosphere. Under stirring, the ε-caprolactam dissolved within 30 minutes. 4.48 g of m-phenylenediamine (32.9 mmol) was added and the mixture was homogenized. Under stirring, a mixture of 8.54 g of intermediate I6 (21.4 mmol) and 27.0 g of intermediate I2 (44.4 mmol) was added dropwise within 30 minutes, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. The result was a transparent light yellow product.

[0237] E10:

[0238] In a glass flask equipped with a stirrer, a reflux condenser and a nitrogen inlet, 34.0 g of ε-caprolactam was dissolved in 51.0 g of N-butyl butyrolactam and stirred at 60 ° C for 30 minutes to obtain a clear solution. Subsequently, 1.17 g of 1,3-diaminopropane (15.8 mmol) was added and briefly homogenized. A uniform mixture of 13.7 g of intermediate I3 (30.0 mmol) and 0.126 g of hexamethylene diisocyanate (0.751 mmol) was added dropwise to the reaction mixture over 25 minutes. The reaction mixture was stirred at 80 ° C for another 3 hours. As a result, a transparent yellow liquid product was obtained.

[0239] E11:

[0240] In a four-necked flask with a stirrer, 21.5 g of ε-caprolactam and 1.25 g of LiCl were added to 32.3 g of N-butylbutyrolactam under stirring. The mixture was heated to 80° C. under a nitrogen atmosphere. Under stirring, ε-caprolactam and LiCl dissolved within 30 minutes. 6.49 g of m-phenylenediamine (47.7 mmol) was added and the mixture was homogenized. Under stirring, 38.5 g of intermediate I1 (95.4 mmol) was added dropwise within 30 minutes, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. The result was a transparent light yellow product.

[0241] E12:

[0242] In a four-necked flask with a stirrer, 26.3 g of ε-caprolactam was added to 48.8 g of N-methylcaprolactam under stirring. The mixture was heated to 80° C. under a nitrogen atmosphere. Under stirring, the ε-caprolactam dissolved within 30 minutes. 3.61 g of m-xylylenediamine (26.5 mmol) was added and the mixture was homogenized. Under stirring, 21.4 g of intermediate I1 (53.0 mmol) was added dropwise within 30 minutes, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. The result was a transparent light yellow product.

[0243] E13:

[0244] In a four-necked flask with a stirrer, 24.5 g of ε-caprolactam was added to 45.5 g of N-methylcaprolactam under stirring. The mixture was heated to 80° C. under a nitrogen atmosphere. Under stirring, the ε-caprolactam dissolved within 30 minutes. 4.33 g of m-phenylenediamine (31.8 mmol) was added and the mixture was homogenized. Under stirring, 25.7 g of intermediate I1 (63.6 mmol) was added dropwise within 30 minutes, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. The result was a transparent light yellow product.

[0245] E14:

[0246] In a four-necked flask with a stirrer, 26.3 g of ε-caprolactam was added to 48.8 g of N-ethylcaprolactam under stirring. The mixture was heated to 80° C. under a nitrogen atmosphere. Under stirring, the ε-caprolactam dissolved within 30 minutes. 3.61 g of m-phenylenediamine (26.5 mmol) was added and the mixture was homogenized. Under stirring, 21.4 g of intermediate I1 (53.0 mmol) was added dropwise within 30 minutes, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. The result was a transparent light yellow product.

[0247] E15:

[0248] In a four-necked flask with a stirrer, 24.5 g of ε-caprolactam was added to 45.5 g of N-ethylcaprolactam under stirring. The mixture was heated to 80° C. under a nitrogen atmosphere. Under stirring, the ε-caprolactam dissolved within 30 minutes. 4.33 g of m-phenylenediamine (31.8 mmol) was added and the mixture was homogenized. Under stirring, 25.7 g of intermediate I1 (63.6 mmol) was added dropwise within 30 minutes, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. The result was a transparent light yellow product.

[0249] E16:

[0250] In a four-necked flask with a stirrer, 22.5 g of ε-caprolactam was added to 52.5 g of N-cyclohexylpyrrolidone under stirring. The mixture was heated to 80° C. under a nitrogen atmosphere. Under stirring, the ε-caprolactam dissolved within 30 minutes. 3.61 g of m-xylenediamine (26.5 mmol) was added and the mixture was homogenized. Under stirring, 21.4 g of intermediate I1 (53.0 mmol) was added dropwise within 30 minutes, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. The result was a transparent light yellow product.

[0251] E17:

[0252] In a four-necked flask with a stirrer, 21.0 g of ε-caprolactam was added to 49.0 g of N-cyclohexylpyrrolidone under stirring. The mixture was heated to 80° C. under a nitrogen atmosphere. Under stirring, the ε-caprolactam dissolved within 30 minutes. 4.33 g of m-xylenediamine (31.8 mmol) was added and the mixture was homogenized. Under stirring, 25.7 g of intermediate I1 (63.6 mmol) was added dropwise within 30 minutes, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. The result was a transparent light yellow product.

[0253] E18:

[0254] In a four-necked flask with a stirrer, 2.5 g of pyrrolidone-2-one was added to 72.5 g of N-butylbutyrolactam under stirring. The mixture was heated to 80° C. under a nitrogen atmosphere. 3.61 g of m-xylylenediamine (26.5 mmol) was added and the mixture was homogenized. 21.4 g of intermediate I1 (53.0 mmol) was added dropwise over 30 minutes under stirring, so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. A transparent light yellow product was obtained as a result.

[0255] E19:

[0256] In a four-necked flask with a stirrer, 5.0 g of pyrrolidone-2-one was added to 65.0 g of N-butylbutyrolactam under stirring. The mixture was heated to 80° C. under a nitrogen atmosphere. 4.33 g of m-xylylenediamine (31.8 mmol) was added and the mixture was homogenized. 25.7 g of intermediate I1 (63.6 mmol) was added dropwise over 30 minutes while stirring so that the temperature did not exceed 85° C. The mixture was then stirred at 80° C. for 3 hours. A transparent light yellow product was obtained as a result.

[0257] Storage stability

[0258] 100 g of the inventive and non-inventive examples were stored at room temperature (23° C.) until noticeable optical changes occurred. Optical changes include gelation of the material and / or precipitation formation.

[0259] Table 3 Results

[0260]

[0261]

[0262] *) Inventive and non-inventive examples with the same Roman numerals are corresponding examples. The inventive examples comprise a solvent and a cyclic amide comprising an amide NH group, while the corresponding non-inventive examples comprise only a solvent. The inventive examples and the corresponding non-inventive examples comprise the same amount of urea compound.

[0263] **) Time between synthesis and formation of precipitate or gel.

[0264] As can be seen from Table 3, inventive examples E1-19 exhibit significantly increased storage stability over their corresponding non-inventive examples.

[0265] Application Testing

[0266] Table 4 Raw materials

[0267]

[0268]

[0269] Test 1: Whitening of water-based two-component PU varnish

[0270] The formulation in Table 5 was used to produce a water-based two-component PU varnish. All components of component A were added to a PE beaker under stirring conditions and homogenized for 10 minutes at room temperature (23°C) using a Dispermat LC3 (VMA Getzmann) (rotation speed of 1000 rpm, tooth plate diameter of 4 cm). The pH value of component A was then adjusted to pH 8.2-8.5 with a DMEA solution (10% aqueous solution). Component B was produced under the same stirring conditions. Component A was divided into small portions (50 g in a 175 ml PE beaker), and the sample of the present invention was added, with the weight percentage of the urea compound added being 0.5% (based on the total transparent coating), and stirred for 5 minutes at room temperature (23°C) using a Dispermat LC3 (VMA Getzmann), with a rotation speed of 1500 rpm and a tooth plate diameter of 2.5 cm.

[0271] After standing overnight at room temperature, the hardener solution was added in the specified mixing ratio and stirred with a spatula to make it uniform. The samples were applied to glass with a frame film applicator (BYK-Gardner GmbH) with a wet film thickness of 120 μm and dried at room temperature for 1 week. For the whitening test, a household sponge (2 cm x 2 cm) soaked in water was placed on the paint film for 24 hours. After the sponge was removed and dried, the degree of whitening of the coating film was directly evaluated visually on a scale of 1-5 (1 = no whitening to 5 = severe whitening).

[0272] Table 5: Waterborne two-component polyurethane varnish system Component A:

[0273]

[0274] Dispermat: Use a 4 cm diameter tooth plate and run at 1000 rpm for 10

[0275] minute

[0276] Adjust the pH to 8.2-8.5 using DMEA solution (10% in deionized water)

[0277] Component B:

[0278] Bayhydur 3100 82.3g

[0279] Dowanol PMA 17.7 g

[0280] 100.0g

[0281] Dispermat: Use a toothed plate with a diameter of 4 cm and run at a speed of 1000 rpm for 5 minutes. Ratio: component A: component B = 50:15 (weight / weight), use

[0282] Spatula Mixing

[0283] Table 6: Whitening results of paint formulations

[0284] Example Whitening Control (without rheological additive) 1 C9 4 E7 1

[0285] As can be seen in Table 6, surprisingly, the use of inventive example E7 has no effect on the blooming of the water-based clearcoat, whereas the use of non-inventive example C9 leads to a significant deterioration of the blooming.

[0286] Test 2: Whitening of solvent-based two-component PU varnish

[0287] The solvent-borne two-component PU varnish was produced using the formulation in Table 7. All components of component A were added to a PE beaker under stirring and homogenized for 10 minutes at room temperature (23° C.) using a Dispermat LC3 (VMA Getzmann) at a speed of 1000 rpm and a tooth plate diameter of 4 cm. Component A was divided into small portions (50 g in a 100 ml glass bottle), and the sample of the invention was added together with a dosage of 0.5% by weight of the urea compound (calculated on the total varnish formulation) under stirring, and stirred for 5 minutes at room temperature (23° C.) using a Dispermat LC3 (VMA Getzmann) at a speed of 1500 rpm and a tooth plate diameter of 2.5 cm.

[0288] After storage overnight at room temperature, the hardener was added in the specified mixing ratio and stirred with a spatula to make it homogenous. The samples were applied to glass with a frame film applicator (BYK-Gardner GmbH) with a wet film thickness of 120 μm and dried at room temperature for 1 week. To evaluate the whitening, a water immersion test was carried out, in which the coatings were placed at 60°C in a 1004 type water bath for 1 week (Gesellschaft für Labortechnik mbH). Immediately after the samples were removed from the bath and dried, the degree of whitening of the paint film was visually evaluated using an evaluation scale of 1-5 (1 = no whitening - 5 = severe whitening).

[0289] Table 7: Solvent-based two-component PU varnish

[0290] Component A:

[0291]

[0292] Dispermat: Use a 4 cm diameter toothed plate and run at 1000 rpm for 10 minutes Component B:

[0293] Desmodur N3390BA 50.0g

[0294] Ratio: Component A: Component B = 2:1 (weight / weight), mix with a spatula

[0295] Table 8: Blooming results for varnish formulations

[0296] Example Whitening Control (without rheological additive) 1 C2 5 E1 1

[0297] Table 8 shows that the use of inventive example E1 has no effect on the blooming of the solvent-based clearcoat, whereas the use of non-inventive example C2 leads to a significant deterioration of the blooming.

[0298] Test 3: Sag resistance of thermoplastic acrylic varnish

[0299] The thermoplastic acrylic varnish was produced using the recipe in Table 9. All ingredients were added to a PE beaker under stirring and homogenized for 15 minutes at room temperature (23° C.) using a Dispermat LC3 (VMA Getzmann) at a speed of 1000 rpm and a tooth plate diameter of 4 cm. The varnish was divided into small portions (50 g in a 100 ml glass bottle), and the sample of the invention and the urea compound in an amount of 0.75 wt % and 1.0 wt % (calculated on the total varnish) were added under stirring, and stirred for 5 minutes at room temperature (23° C.) using a Dispermat LC3 (VMA Getzmann) at a speed of 1500 rpm and a tooth plate diameter of 2.5 cm. After standing overnight at room temperature, the samples were tested for sag resistance using a step scraper Model 421 / S (Erichsen GmbH & Co KG), and the wet film thicknesses were 50-500 μm and 550-1000 μm, respectively. The coating was applied on a comparison card 2801 (BYK-Gardner GmbH) using an automatic applicator byko-drive XL (BYK-Gardner GmbH) at a coating speed of 50 mm / s. Immediately after application, the coating was hung vertically at room temperature until dry. After drying, the sag resistance was visually inspected. The wet film thickness was therefore considered to be a clear separation of the coating after drying, with no runners and bulges between the applied film thicknesses.

[0300] Table 9: Solvent-based Thermoplastic Acrylic Clear Coatings

[0301]

[0302] Dispermat: Use a 4 cm diameter toothed plate and run at 1000 rpm for 15 minutes

[0303] Table 10: Anti-sagging results of clear coat formulations

[0304]

[0305]

[0306] As can be seen from Table 10, the application of inventive example E1 in the thermoplastic acrylic varnish shows better sag resistance than non-inventive example C2.

[0307] Test 4: Gel Strength and Turbidity in Various Solvents

[0308] The various solvents in Table 11 were charged into a 100 ml glass bottle in an amount of 50 g. The sample of the present invention was added together with a dosage of 1.0 wt % of the urea compound (calculated based on the amount of solvent) under stirring, and stirred for 5 minutes at room temperature (23° C.) using a Dispermat LC3 (VMA Getzmann) at a rotation speed of 1500 rpm and a tooth plate diameter of 2.5 cm. After being stored at room temperature (23° C.) overnight, the gel strength and turbidity of the sample were evaluated. The visual evaluation range of gel strength ranged from strong gel to no gel (evaluation level 1 (strong gel) to 5 (no gel), and the turbidity ranged from no turbidity to strong turbidity (level 1 (no turbidity) to 5 (strong turbidity)).

[0309] Table 11: Test Solvents

[0310]

[0311] Table 12 Results Gel strength

[0312]

[0313] *) Embodiments of the present invention and embodiments not of the present invention that share the same Roman numerals are corresponding embodiments.

[0314] It can be concluded from Table 12 that the gel strengths of Examples E1, E2, E3, E6, E7 and E11 of the present invention in the corresponding solvents are better than those of Comparative Examples C2, C4, C7, C9 and C14.

[0315] Table 13 Results Turbidity

[0316]

[0317]

[0318] *) Embodiments of the present invention and embodiments not of the present invention that share the same Roman numerals are corresponding embodiments.

[0319] It can be concluded from Table 13 that the application examples including the embodiments E1, E2, E3, E6, E7 and E11 of the present invention have lower turbidity in the corresponding solvents than the non-inventive examples C2, C4, C7, C9 and C14.

[0320] Test 5: Rheological effects in various oils and very low polarity solvents

[0321] The various oils or very low polarity solvents in Table 14 were charged in an amount of 50 g in a 100 ml glass bottle. The samples of the invention were added with a dosage of 1.0 wt % of the urea compound (calculated on the amount of oil / solvent) under stirring, using a Dispermat LC3 (VMA Getzmann) at room temperature (23° C.) for 5 minutes, 1500 rpm, 2.5 cm diameter tooth plate. After storage at room temperature overnight, the gel strength of the samples was evaluated. The visual evaluation of the gel strength ranged from strong gel (1) to no gel (5).

[0322] Table 14: Tested Oils and Very Low Polarity Solvents

[0323] Synthetic oil XP07 (XP07)

[0324] Petroleum LVT 200 (LVT)

[0325] Shell Saraline 185V(185V)

[0326] Heptane

[0327] Pentane

[0328] Isopar H (Iso H)

[0329] White spirit K30(K30)

[0330] Table 15: Gel strength results in various oils / low polarity solvents

[0331]

[0332] As can be seen from Table 15, Example E10 of the present invention exhibits better gel strength in the corresponding oils and low-polarity solvents than Example C13 not of the present invention.

Claims

1. A composition comprising - a cyclic amide comprising at least one amide NH group, - a solvent, the solvent being different from a cyclic amide comprising at least one amide NH group, and wherein the solvent comprises at least one of an amide group and a sulfoxide group, wherein the amide nitrogen of the amide group has two substituents, wherein the substituents are selected from aliphatic and aromatic groups, and - a urea compound having a number average molecular weight of at least 350 g / mol.

2. The composition of claim 1, wherein the solvent comprises at least one of N-substituted cyclic amides, non-cyclic dialkylamides of monofunctional and difunctional carboxylic acids, and sulfoxides.

3. The composition according to claim 1 or 2, wherein the cyclic amide consists of C, H, O and N atoms.

4. The composition according to any one of the preceding claims, wherein the cyclic amide has a molecular weight of 71 to 250 g / mol.

5. A composition according to any one of the preceding claims, wherein the cyclic amide comprises at most 2 amide groups.

6. The composition according to any one of the preceding claims, wherein the cyclic amide comprises at least one of ε-caprolactam, γ-butyrolactam, δ-valerolactam and mixtures thereof.

7. The composition according to any one of the preceding claims, wherein the urea compound is a ureaurethane.

8. The composition according to any one of the preceding claims, wherein the urea compound comprises at least 2 urea groups and at least 2 urethane groups.

9. The composition according to any one of the preceding claims, wherein the urea compound has a number average molecular weight of 400 to 30000 g / mol.

10. A composition according to any preceding claim, wherein the composition is liquid at 25°C and 1013 mbar.

11. The composition according to any one of the preceding claims, wherein the composition comprises from 0.1 to 15.0 wt% of the salt, calculated on the total weight of the cyclic amide, at least one solvent, the urea compound and the salt.

12. A composition according to any one of the preceding claims, wherein the composition comprises 1 to 60% by weight of a cyclic amide containing at least one amide NH group, 5 to 70 wt. % of a solvent, the solvent being different from a cyclic amide comprising at least one amide NH group, and wherein the solvent comprises at least one of a dialiphatic substituted amide group and a sulfoxide group, 5-60 wt % of a urea compound having a number average molecular weight of at least 350 g / mol, It is calculated based on the total weight of the cyclic amide, solvent and urea compound.

13. Use of a composition according to any one of the preceding claims for controlling the rheology of a liquid composition, wherein the liquid composition is liquid at 23°C and 1013 mbar.

14. A liquid composition comprising the composition according to any one of the preceding claims 1 to 12 and a binder, wherein the liquid composition is liquid at 23°C and 1013 mbar.

15. A coated article, wherein at least a portion of a surface of the article is coated with the liquid composition according to claim 14.

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