Composition containing cyclic amide

Abstract

Provided are high-quality rheology control agents having good effectiveness and usable in a number of application systems, rheology control agents that result in improved storage stability, and rheology control agents substantially free of salts. 【Solution】The present invention relates to 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, the solvent containing at least one of an amide group and a sulfoxide group, the amide nitrogen of the amide group having two substituents, the substituents being selected from an aliphatic group and an aromatic group, and a urea compound having a number average molecular weight of at least 350 g / mol.

Description

Technical Field

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

Background Art

[0002] In fields such as coating materials, adhesives, sealants, and molding compounds, as well as non-aqueous oil drilling fluids, it is necessary to adjust the rheological properties of the liquid system mainly by adjusting the viscosity. This can be done by selecting a binder, a solvent, and the concentration of pigments and / or fillers. In many cases, the addition of so-called rheology additives to such liquids is required. The effect of these additives lies in adjusting the rheological properties of the system such as viscosity and viscoelasticity. By doing so, the system properties are usually improved with respect to sag resistance, improvement of storage stability (by reducing sedimentation of solid particles), or overall viscosity increase (often referred to as "thickening").

[0003] The rheology of liquid systems is often controlled using clays such as bentonite and / or silica, which may optionally be organically modified hydrogenated castor oil and polyamide wax. Disadvantages of such rheology control aids are that they are almost dry solids and must be in a semi-finished form by treatment with a solvent or shear force, and / or must be introduced into the liquid system by targeted temperature control. If such temperature and / or appropriate introduction conditions are not observed, not only will the rheology performance be insufficient, but the product may also have harmful properties.

[0004] When the liquid system is a coating composition, such rheology control aids often cause cases of cloudiness and haze in clear or transparent coatings. Furthermore, dry powder products cause dust during processing, and operations involving such dry powder products may not be technically preferable.

[0005] The application of a liquid in place of such a rheology control aid is provided by a solution of specific urea components as described, for example, in EP 1188779. Typically, the solvent and / or carrier medium is a polar / aprotic solvent. Alternatively, ionic liquids can be used, as described in DE 102008059702, in place of classical organic diluents.

[0006] One further aspect worthy of note in relation to rheology control aids provided in liquid form is their storage stability. For example, an extended storage time or increased stress during storage can lead to a decrease in storage stability and thus a decrease in efficiency in the system in question, especially in cases where storage involves temperature fluctuations. Therefore, it is desirable for the rheology control aid to have good storage stability and not to precipitate easily during storage.

[0007] To prevent early precipitation during storage, a small amount of a salt that acts as a stabilizer, especially a halide such as LiCl, is usually added. Since salts, especially in the case of halides such as LiCl, also cause many problems with regard to application performance, such ionic compounds have an adverse effect on properties such as the influence on corrosion caused by the coating system, environmental effects, discoloration and whitening, the resistance of the coated material to contamination, and conductivity.

[0008] All of the above parameters impose restrictions on the selection of suitable preparations. Therefore, the selection of a suitable rheology control aid is not easy. This is because a suitable rheology control aid must show compatibility with subsequent application systems in particular and must meet a number of requirements. A suitable rheology control aid must show not only improvement in rheological activity in the application system but also broad compatibility in the formulations related to the application. There is still a need to provide improved rheology additives. By using improved rheology additives, a very reliable and increased thickening effect should be produced in various formulations, but on the other hand, the storage stability of such rheology control aids needs to be favorable.

Prior Art Documents

Patent Documents

[0009]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0010] Therefore, a specific object of the present invention is to provide a high-quality rheology control agent having good effectiveness and usable in a number of application systems. More specifically, the aim was to find a rheology control agent that produces remarkable sag resistance behavior. Another object of the present invention is to provide a rheology control agent that produces improved storage stability, and a further object of the present invention is to provide a rheology control agent substantially free of salts.

Means for Solving the Problems

[0011] Surprisingly, 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, the solvent containing at least one of an amide group and a sulfoxide group, the amide nitrogen of the amide group having two substituents, the substituents being selected from an aliphatic group and an aromatic group, and a urea compound having a number average molecular weight of at least 350 g / mol.

[0012] A urea compound is a compound containing at least one urea group. In one embodiment, the urea compound is a urea urethane compound. In another embodiment, the urea component contains a molecule containing at least one urea group and at least one urethane group. In another embodiment, the urea component contains a molecule containing at least one urea group and at least two urethane groups. In another embodiment, the urea component contains a molecule containing at least two urea groups, and in a different embodiment, the urea compound contains two urea groups and two urethane groups. In yet another embodiment, the urea component contains a molecule containing at least four urea groups or more than four urea groups. In a different embodiment, the urea component contains a molecule containing at least two urea groups and at least two urethane groups. In a different embodiment, the urethane group may not be present.

[0013] Preferably, the urea-based compounds described in claim 11 of WO 2015 / 158407, claim 13 of WO 2015 / 158407, claim 16 of WO 2015 / 158407, and claim 1 of EP 1396510 A1 are used.

[0014] A preferred class of urea compounds can be represented by the following general formula (U-1): R31-[R33-Z-R34-W-] n -R32 (U-1) Here, R31 and R32 are, independently of each other and independently for each occurrence, branched or unbranched saturated or unsaturated organic groups containing 1 to 100 carbon atoms and each having at most 1 urea group and at most 1 urethane group, and R33 and R34 are, independently of each other and independently for each occurrence, branched or unbranched polyester groups containing 1 to 300 carbon atoms and optionally containing ether groups, branched or unbranched polyether groups containing 2 to 300 carbon atoms, branched or unbranched polyamide groups containing 1 to 300 carbon atoms, polysiloxane groups containing 3 to 100 silicon atoms, branched or unbranched C2-C22 alkylene groups, branched or unbranched C2-C22 cycloalkylene groups, branched or unbranched C2-C18 alkenylene groups, C6-C12 arylene groups and / or branched or unbranched C7-C22 arylalkylene groups. Z and W, independently of each other, represent NH-CO-O and / or NH-CO-NH, and when Z and W occur multiple times, Z and W independently represent the above groups. n represents an integer from 1 to 150, preferably from 2 to 150, and when n occurs multiple times, n independently represents an integer from 1 to 150, preferably from 2 to 150.

[0015] In another preferred embodiment, the urea compound is of general formula (U-2a), (U-2b), (U-2c), (U-2d), and (U-2e)

Chemical formula

[0016] Preferably, the urea compound has the structure of formula (U-2a), where RP1 is a hydrocarbyl group having 4 to 24 carbon atoms, or a polyether segment having up to 50 alkylene oxide repeating units, preferably segment Q-(O-AO) r selected from, where Q is a C1-C18 alkyl or alkenyl group, AO is the group C2H4 or C3H6, and r is an integer from 2 to 35. IC1 and IC2 are preferably the following divalent groups (the " * " indicates the bonding site) [Chemical formula] Selected from one of the following, where AM is a group C2H4, C3H6, C4H8, C5H 10、 C6H 12 C6H 10、 -CH2-C6H4-CH2, or a group [Chemical formula] Selected from, where R x and R y represent H or CH3.

[0017] In a highly preferred embodiment of (U-2a), IC1 and / or IC2 are [Chemical formula] Selected from.

[0018] Even more preferably, IC1 and IC2 are [Chemical formula] Selected from.

[0019] In a highly preferred embodiment of (U-2a), AM is selected from C2H4 and -CH2-C6H4-CH2-.

[0020] In a highly 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.

[0021] In another preferred embodiment, the urea compound has a structure according to formula (U-2b), where Preferred embodiments of IC1 and IC2 are as described for (U-2a), in particular a group C7H6, or a group -C6H4-CH2-C6H4- AM1 and AM2 are selected from linear or branched, saturated or unsaturated C1-C24 alkyl or alkenyl groups, or the group C6H5-CH2- RP3 is selected from a hydrocarbyl group having 2 to 20 carbon atoms, or a polyether segment having 1 to 40 ether oxygen atoms, preferably a polyether segment containing 1 to 30 ethylene oxide and / or propylene oxide repeating units.

[0022] In a further preferred embodiment, the urea compound has a structure according to formula (U-2c), wherein Preferred embodiments of AM1 and AM2 are as described for (U-2b), Preferred embodiments of AM are as described for (U-2a), IC4 is a group as described for IC1 and IC2, or a urethane group containing a segment having the following structure -[IC2-NH-(C=O)-O-RP3-O-(C=O)-NH-IC2]- wherein IC2 is defined as described for (U-2a) and RP3 is defined as described for (U-2b).

[0023] For (U-2c), it is particularly preferred that IC4 is selected from the group C7H6, the group -C6H4-CH2-C6H4-, and the group -[IC2-NH-(C=O)-O-RP3-O-(C=O)-NH-IC2]- wherein IC2 represents the group C7H6 or the group -C6H4-CH2-C6H4-, and RP3 represents a polyether segment containing 1 to 30 ethylene oxide and / or propylene oxide repeating units.

[0024] In a preferred embodiment of (U-2c), q is an integer from 0 to 15, more preferably from 0 to 7, most preferably from 0 to 4, for example 1 to 4.

[0025] In a preferred embodiment, at least 50% by weight of the urea compound of the composition of the present invention has a structure according to formula (U-2a) or (U-2c).

[0026] In a highly preferred embodiment, at least 50% by weight of all the urea compounds of the composition of the present invention have a structure according to formula (U-2a), where m is 0 or m is 1 to 5, and very preferably, m is 0.

[0027] In a preferred embodiment, the urea compound is a urethane urea, and 95 to 100% by weight of the urea compound contains at least one molecular segment of the general formula (U-3a) O-CO-NH-Y1-NH-CO-NH- (U-3a) where Y1 represents a saturated or unsaturated branched or unbranched hydrocarbon group containing 6 to 20 carbon atoms. When Y1 appears multiple times, Y1 independently represents a saturated or unsaturated branched or unbranched hydrocarbon group containing 6 to 20 carbon atoms. and in each case, does not contain the molecular segment of the general formula (U-3b) O-CO-NH-Y2-NH-CO-O- (U-3b) where Y2 represents a saturated or unsaturated, branched or unbranched hydrocarbon group containing 6 to 20 carbon atoms. When Y2 appears multiple times, Y2 independently represents a saturated or unsaturated branched or unbranched hydrocarbon group containing 6 to 20 carbon atoms.

[0028] Urea-based compounds can be prepared by reacting the corresponding isocyanate and amine in a known manner, for example, by reacting with the amine or isocyanate described in claim 14 of WO 2015 / 158407. Methods for producing this type of urea compound are described in more detail, for example, in US Patent No. 7,250,487, US Patent No. 7,348,397, European Patent Application Publication No. 1,396,510, and European Patent Application Publication No. 2,292,675.

[0029] The synthesis of the urea compound can preferably be carried out directly in the presence of a cyclic amide and a solvent. In another embodiment, the urea compound is synthesized in the presence of a solvent, and then the cyclic amide is added. In yet another embodiment, the urea compound is synthesized in the presence of a cyclic amide, and then the solvent is added. In a further embodiment, the urea compound is synthesized in the presence of a cyclic amide and one solvent, and then a second solvent different from the first solvent is added.

[0030] The urea compound preferably has a number average molecular weight of 400 g / mol to 30,000 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 greater than 600 g / mol, even more preferably greater than 650 g / mol, and most preferably greater than 800 g / mol. Further, the number average molecular weight (Mn) of the urea compound is preferably less than 20,000 g / mol, more preferably less than 10,000 g / mol, and most preferably less than 8000 g / mol. Preferably, the number average molecular weight (Mn) is 650 g / mol to 20,000 g / mol, more preferably 800 g / mol to 8000 g / mol, and even more preferably 800 g / mol to 5000 g / mol.

[0031] In a further preferred embodiment, the number average molecular weight is at least 800 g / mol, preferably 1000 g / mol, preferably at least 1500 g / mol, preferably 1500 g / mol to 20,000 g / mol, more preferably 1500 g / mol to 8000 g / mol, and even more preferably 1500 to 5000 g / mol.

[0032] The number average molecular weight and the weight average molecular weight can be determined by gel permeation chromatography in accordance with DIN EN ISO 13885-2 (November 2021) (eluent: dimethylacetamide solution of lithium bromide (content 5 g / l), standard substance: polymethyl methacrylate, column temperature: 50 °C). Also, the number average molecular weight may be determined by calculation. Furthermore, the number average molecular weight of small molecules up to 1000 g / mol can also be determined by other methods such as mass spectrometry or nuclear magnetic resonance spectroscopy.

[0033] The composition according to the invention comprises a solvent different from a cyclic amide containing at least one amide NH group, the solvent containing at least one of an amide group and a sulfoxide group, the amide nitrogen of the amide group having two substituents, the substituents being selected from aliphatic groups and aromatic groups. The amide nitrogen of the amide group has two substituents, which means that the amide group must not be an NH amide group.

[0034] The solvent preferably comprises at least one of N-substituted cyclic amides, acyclic dialkylamides of monofunctional and bifunctional carboxylic acids, N-acylmorpholines, and sulfoxides.

[0035] Suitable solvents are, for example, N-substituted cyclic amides: N-alkyl lactams, preferably N-alkyl butyrolactams, N-alkyl valerolactams, and N-alkyl caprolactams, where the alkyl group preferably has 1 to 18 carbon atoms, more preferably 1 to 12 carbon atoms, even more preferably 1 to 8 carbon atoms, and furthermore hydroxyalkyl lactams (e.g. hydroxyethyl pyrrolidone). A cyclic amide is an amide in which the amide nitrogen and the amide carbonyl carbon are part of a cyclic structure.

[0036] Further suitable solvents are acyclic dialkylamides of monofunctional and bifunctional carboxylic acids: N,N-dialkylamides of C1-C18 monocarboxylic acids, bis(N,N-dialkyl)amides of C1-C18 dicarboxylic acids; optionally, these carboxylic acids may contain a hydroxyl group, an ether group or an ester group, and said solvents are for example, N,N-dialkylamide alkyl esters, N,N-dialkylamide alkyl ethers, N,N-dialkyl lactamides. Sulfoxides are also suitable, preferably dimethyl sulfoxide. An acyclic amide is an amide in which neither the amide nitrogen nor the amide carbonyl carbon is part of a cyclic structure. Under this definition, for example, N-formylmorpholine is considered an acyclic amide.

[0037] Further suitable solvents are acyclic amides obtainable from the reaction of diamines with monocarboxylic acids. Suitable examples are the reaction products of C1-C18 monocarboxylic acids with C2-C12 alkylene diamines.

[0038] 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.

[0039] Suitable solvents are also linear amides, for example, N,N-dimethylformamide, N,N-dimethylacetamide, N,N-dimethylamides of C3-C18 monocarboxylic acids (preferably N,N-dimethylamides of C6-C10 monocarboxylic acids), N,N-dialkylamide alkyl esters, N,N-dialkylamide alkyl ethers, and acylmorpholines.

[0040] Preferred examples of these are also N,N-dialkylamide alkyl esters, N,N-dialkylamide alkyl ethers, N-formylmorpholine and N-acetylmorpholine.

[0041] Another suitable solvent is N-acetylcaprolactam.

[0042] Preferably, the solvent is liquid at 23 °C and 1013 mbar.

[0043] The composition according to the invention comprises a cyclic amide containing 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.

[0044] The cyclic amide preferably contains at most 2 amide groups. In another embodiment, the cyclic amide preferably contains 2 amide groups, and in yet another embodiment, the cyclic amide contains exactly 1 amide group.

[0045] Preferably, the cyclic amide consists of C atoms, H atoms, O atoms and N atoms. That is, the cyclic amide consists only of these atoms and there are no other atoms not mentioned.

[0046] Preferably, the cyclic amide is a lactam. A lactam is a cyclic amide having an amide group. Preferably, the cyclic amide contains at least one of ε-caprolactam, γ-butyrolactam, δ-valerolactam, and mixtures thereof.

[0047] Furthermore, cyclic amides in which one or more carbon atoms that are part of the ring have substituents, preferably aliphatic substituents, are suitable.

[0048] The cyclic amide preferably has a molecular weight of 71 - 250 g / mol. More preferably, the cyclic amide has a molecular weight of 85 - 220 g / mol. Even more preferably, the cyclic amide has a molecular weight of 85 - 198 g / mol, and most preferably, the cyclic amide has a molecular weight of 85 - 145 g / mol, such as 99 - 130 g / mol or 99 - 115 g / mol.

[0049] The cyclic amide and the solvent are preferably present in a weight ratio of 0.5:99.5 to 60.0:40.0. More preferably 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 the 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.

[0050] Preferably, the amount of the cyclic amide relative to the total weight of the cyclic amide and the solvent 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%, for example at least 20.0% or at least 25.0%. Also preferably, the amount of the cyclic amide relative to the total weight of the cyclic amide and the solvent is at most 55.0%, preferably at most 50.0%, more preferably at most 45.0%, for example at most 40.0% or at most 37.5%.

[0051] Generally, the composition is liquid at 23 °C and 1013 mbar.

[0052] The composition preferably contains a salt in an amount of 0.1 to 15.0% by weight, calculated relative to the total weight of the cyclic amide, at least one solvent, a urea compound and the salt.

[0053] Generally, the composition can contain one or more salts. The salts according to the present invention include cations of elements in Group 1 and Group 2 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 include lithium cations, calcium cations or magnesium cations, particularly preferably salts containing lithium cations and calcium cations, preferably in the form of chlorides, acetates and / or nitrates. In some embodiments, the salt contains, as anions, preferably monovalent anions, particularly preferably halide ions, pseudohalide ions, formate ions, acetate ions and / or nitrate ions, most particularly preferably chloride ions, acetate ions and / or nitrate ions.

[0054] Particularly preferred salts are inorganic lithium salts such as lithium chloride and lithium nitrate, and ammonium salts such as alkylammonium salts, particularly quaternary ammonium salts such as tetraalkylammonium halides.

[0055] The composition preferably contains 0.1 to 15.0% by weight of the salt, where the % by weight is calculated based on the weight of the cyclic amide, the solvent, the urea compound and the salt. Preferably, the composition contains the salt in an amount of 0.1 to 10.0% by weight, more preferably 0.1 to 8.0% by weight, even more preferably 0.1 to 5.0% by weight, and most preferably 0.1 to 3.0% by weight.

[0056] In a preferred embodiment, the compound does not contain or contains a low amount of salts selected from lithium salts and halide salts. The low amount means a salt amount not exceeding 1.0% by weight when calculated based on the weight of the composition, more preferably this amount does not exceed 0.5% by weight, more preferably this amount does not exceed 0.3% by weight, and preferably does not exceed 0.1% by weight.

[0057] In a further preferred embodiment, the composition is salt-free. When the composition is salt-free, it is preferably such that the salt content, calculated with respect to the weight of the composition, does not exceed 0.50% by weight, more preferably does not exceed 0.30% by weight, preferably does not exceed 0.10% by weight, and for example preferably does not exceed 0.05% by weight.

[0058] In some embodiments, the composition further comprises a surfactant. Preferably, the salt in the composition can be replaced with a surfactant. Preferably, the salt can be completely replaced with a surfactant, but it is also possible to add the surfactant together with the salt. In the latter case, it is possible to partially replace the salt with a surfactant to reduce the salt content, or it is also possible to add the surfactant together with the salt and leave the salt content unchanged. Suitable surfactants include 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, alkylamidobetaines, imidazolines. Particularly preferred are quaternary ammonium salts and sulfosuccinates. Preferably, the surfactant is used in an amount of 0.1 to 15.0% by weight, preferably 0.2 to 14.0% by weight, more preferably 0.4 to 13.0% by weight, even more preferably 0.5 to 12.0% by weight, most preferably 0.8 to 11.0% by weight, for example 1.0 to 10.0% by weight, calculated with respect to the total weight of the composition.

[0059] Preferably, when calculated with respect to the total weight of the cyclic amide, the solvent and the urea compound, the composition contains the following: 1 to 60% by weight of a cyclic amide containing at least one amide NH group, A solvent different from a cyclic amide containing at least one amide NH group, which is 5 to 70% by weight, and the solvent contains at least one of a dialiphatic-substituted amide group and a sulfoxide group. A urea compound that is 5 to 60% by weight and has a number average molecular weight of at least 350 g / mol.

[0060] In a particularly preferred embodiment, the composition contains the following when calculated based on the total weight of the cyclic amide, the solvent, and the urea compound: 2 to 55% by weight of a cyclic amide containing at least one amide NH group. A solvent different from a cyclic amide containing at least one amide NH group, which is 10 to 65% by weight, and the solvent contains at least one of a dialiphatic-substituted amide group and a sulfoxide group. 10 to 55% by weight of a urea compound having a number average molecular weight of at least 350 g / mol.

[0061] In a more preferred embodiment, the composition contains the following when calculated based on the total weight of the cyclic amide, the solvent, and the urea compound: 5 to 50% by weight of a cyclic amide containing at least one amide NH group. A solvent different from a cyclic amide containing at least one amide NH group, which is 15 to 60% by weight, and the solvent contains at least one of a dialiphatic-substituted amide group and a sulfoxide group. 15 to 50% by weight of a urea compound having a number average molecular weight of at least 350 g / mol.

[0062] In an even more preferred embodiment, the composition contains the following when calculated based on the total weight of the cyclic amide, the solvent, and the urea compound: 10 to 45% by weight of a cyclic amide containing at least one amide NH group. A solvent different from a cyclic amide containing at least one amide NH group, which is 20 to 55% by weight, and the solvent contains at least one of a dialiphatic-substituted amide group and a sulfoxide group. A urea compound having a number average molecular weight of at least 350 g / mol and being 16 to 45% by weight.

[0063] In a further preferred embodiment, the composition comprises, when calculated based on the total weight of the cyclic amide, the solvent and the urea compound: 10 to 45% by weight of a cyclic amide containing at least one amide NH group, 25 to 50% by weight of a solvent different from the cyclic amide containing at least one amide NH group, the solvent being one containing at least one of a dialiphatic-substituted amide group and a sulfoxide group, 17 to 40% by weight of a urea compound having a number average molecular weight of at least 350 g / mol.

[0064] In a very preferred embodiment, the composition comprises, when calculated based on the total weight of the cyclic amide, the solvent and the urea compound: 15 to 40% by weight of a cyclic amide containing at least one amide NH group, 25 to 50% by weight of a solvent different from the cyclic amide containing at least one amide NH group, the solvent being one containing at least one of a dialiphatic-substituted amide group and a sulfoxide group, 18 to 38% by weight of a urea compound having a number average molecular weight of at least 350 g / mol.

[0065] In another preferred embodiment, the composition comprises, when calculated based on the total weight of the cyclic amide, the solvent and the urea compound: 15 to 25% by weight of a cyclic amide containing at least one amide NH group, 25 to 50% by weight of a solvent different from the cyclic amide containing at least one amide NH group, the solvent being one containing at least one of a dialiphatic-substituted amide group and a sulfoxide group, 19 to 35% by weight of a urea compound having a number average molecular weight of at least 350 g / mol.

[0066] In yet another preferred embodiment, the composition comprises the following when calculated based on the total weight of the cyclic amide, the solvent, and the urea compound: 15 to 20% by weight of a cyclic amide containing at least one amide NH group, 30 to 50% by weight of a solvent different from the cyclic amide containing at least one amide NH group, the solvent being a solvent containing at least one of a dialiphatic-substituted amide group and a sulfoxide group, 20 to 33% by weight of a urea compound having a number average molecular weight of at least 350 g / mol.

[0067] In a specific embodiment, the composition comprises at least two solvents different from each other, provided that one of the solvents is dimethyl sulfoxide (DMSO) and the second solvent is a solvent containing at least one dialiphatic-substituted amide group. The weight of DMSO relative to the total weight of DMSO, the second solvent containing at least one dialiphatic-substituted amide group, and the cyclic amide containing at least one amide NH group is preferably at least 1%, more preferably at least 2%, even more preferably at least 5%, still more preferably at least 7%, and most preferably at least 10%. The weight of DMSO relative to the total weight of DMSO, the second solvent containing at least one dialiphatic-substituted amide group, and the cyclic amide containing at least one amide NH group is preferably at most 60%, more preferably at most 50%, even more preferably at most 45%, still more preferably at most 40%, most preferably at most 35%, for example at most 30%.

[0068] Furthermore, the present invention relates to the use of the composition for controlling the rheology of a liquid composition. The term "liquid composition" according to the present invention means a composition that is liquid at 23°C and 1013 mbar.

[0069] The composition of the present invention can be used for controlling the rheology of various types of liquid compositions. Thus, in one embodiment, the liquid composition may be an aqueous composition. The main or even the only liquid diluent of the liquid aqueous composition is water. Further, the aqueous composition may contain an amount of organic diluent. The organic diluent is at least one solvent different from a cyclic amide containing at least one amide NH group, the solvent containing at least one of an amide group and a sulfoxide group, the amide nitrogen of the amide group having two substituents, the substituents being selected from aliphatic groups and aromatic groups, and being the same as or different from the solvent. The liquid aqueous composition preferably 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 the organic diluent, calculated based on the total weight of the liquid composition. In a specific embodiment, the liquid aqueous composition contains no organic diluent at all.

[0070] Generally, the liquid aqueous composition contains 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 can contain at least 25% by weight, more preferably at least 30% by weight of water. Generally, the liquid aqueous composition contains up to 90% by weight, for example up to 80% by weight, or up to 70% by weight of water. In a specific embodiment, the liquid aqueous composition contains up to 95% by weight, or even up to 97% by weight, up to 98% by weight, or up to 99% by weight of water.

[0071] In another embodiment, the liquid composition may be a non-aqueous composition. The non-aqueous composition substantially does not contain water. This means that the water contained in the liquid composition is preferably less than 0.0 to 10.0% by weight, preferably 0.0 to 7.0% by weight, calculated based on the total weight of the liquid composition. More preferably, the water contained in the non-aqueous liquid composition is less than 5.0% by weight. For example, the water contained in the liquid composition is less than 3.0% by weight or less than 1.0% by weight, calculated based on the total weight of the liquid composition.

[0072] Suitably, the liquid composition is selected from coating compositions, clear coat compositions, lacquers, varnishes, plastic formulations, pigment pastes, effect pigment pastes, polymer formulations, sealant formulations, cosmetic formulations, home care or industrial care formulations (including perfume and fragrance formulations), ceramic formulations, adhesive formulations, liquid formulations for gas and oil production applications, compositions for the manufacture of electronic components and electronic circuits, liquid formulations for energy storage media applications, detergents, potting compounds, building material formulations, lubricants, filling compounds, wax emulsions, metalworking fluids, metal processing products, liquid compositions in the form of aerosols, so-called spreading agents (for example, for use in plant protection agents or for general purposes of reducing scattering), inks, printing inks, and inkjet inks, or compositions that can be used as corrosion inhibitors in the field of marine and protective coatings, and mixtures thereof.

[0073] Further liquid compositions in which the composition according to the invention can be used are solvent-based or solventless paints, printing inks and inks and lacquers, for example lacquers for varnishing plastics, enamels for wires, floor coverings, coating compositions for coating food and seeds, and so-called color resists used in color filters in flat panel displays such as liquid crystal displays. The field of lacquers to be applied also includes paste-like materials with a very high proportion of solids and a low proportion of liquid components, for example so-called pigment pastes, or pastes based on effect pigments, for example pastes based on metal effect pigments such as aluminum pigments, silver pigments, brass pigments, zinc pigments, copper pigments, bronze pigments such as aurora bronze, flame-colored bronze or iron aluminum oxide pigments. Effect pigments also include, for example, interference pigments or nacreous pigments, such as metal oxide mica pigments, fish silver, bismuth oxychloride or basic lead carbonate.

[0074] Plastic formulations can be liquid or non - liquid starting materials for the production of plastic materials, which are preferably converted into duromers by chemical cross - linking treatment (“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). These can be cured under a very wide variety of conditions, for example, at room temperature (low - temperature curing systems) or at high temperature (high - temperature curing systems), and can optionally be cured under pressure (“closed mold” applications, sheet - molding compounds or bulk - molding compounds). Plastic formulations also include PVC plastisols.

[0075] Cosmetic preparations can be various liquid compositions used in the so - called personal care or health care fields, for example, lotions, creams, pastes, such as toothpaste, foams, such as shaving foam, gels, such as shaving gel, shower gel, or active ingredients in gel formulations, hair shampoos, liquid soaps, nail polishes, lipsticks, and hair dyes.

[0076] The so - called wax emulsions are preferably dispersions of solid waxes in granular form at room temperature in water or an organic medium.

[0077] Building material formulations can be liquid or paste - like materials used in the construction field and which solidify after a curing treatment. For example, hydraulic binders, such as concrete, cement, mortar, tile adhesives, and plaster.

[0078] The fluid for metal processing may be a cutting fluid, a fluid for hole - making (e.g., those used in metal processing), or a forging fluid or lubricants in general. Potential other areas are release agents (in many cases, in the form of aqueous emulsions, e.g., for aluminum die - casting and casting applications), casting detergents (casting coatings), and liquids for surface treatment of metals (e.g., "surface finishing", surface treatment and plating).

[0079] A lubricant is a means used for lubrication, that is, a means that reduces friction and wear and plays a role in providing force, cooling property, vibration damping, sealing action and corrosion protection, and here a liquid lubricant is preferred.

[0080] Detergents can be used for cleaning a wide range of objects, for example, in the areas of home care or industrial care. Detergents affect or assist in the removal of impurities, residues, and deposits. Detergents include laundry detergents (mainly for washing textiles, their precursors, leather, and dishes), and personal care products. Formulations containing perfumes and other fragrances (as liquid raw materials or in encapsulated form), for example, as perfume gels, also belong to this application area.

[0081] The liquid formulations for gas and oil production applications are formulations used for the development and utilization of deposits. Drilling fluids or "drilling mud" are preferred examples. Another application example is the liquid used for the preparation or implementation of the hydraulic fracturing process, as well as the liquid that supports gas and oil production processes.

[0082] An adhesive may be any adhesive material that is liquid under the processing conditions and enables the joining of members by surface adhesion and internal strength.

[0083] The liquid composition of the present invention can further contain conventional additives. Examples of additives are anti-blocking agents, stabilizers, antioxidants, pigments, wetting agents, dispersants, emulsifiers, additional rheology additives, UV absorbers, free radical scavengers, slip additives, defoamers, adhesion promoters, leveling agents, waxes, nanoparticles, film-forming aids, and flame retardants. Preferred additives are wetting agents, dispersants and / or emulsifiers and rheology additives different from the composition of the present invention, for example, clay-based thickeners (including organic clays), (poly)amides, polysaccharides (such as cellulose derivatives, guar, xanthan, etc.), polyacrylates or associative thickeners. For example, the composition of the present invention can be used in combination with other thickeners that affect the low, medium and / or high shear performance of a liquid composition that requires modification with respect to its rheological behavior.

[0084] In a further embodiment of the present invention, 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 in particular the liquid compositions described above. The step of mixing each component can be carried out by current processes known to those skilled in the art. Such processes can include in particular mixing by manual or electric means. Mixing means uniting the compositions and applying a shear force to the united compositions.

[0085] The present invention further relates to a liquid composition comprising a composition according to the present invention and a binder. Preferably, the binder comprises at least one of an alkyd resin (e.g., short oil alkyd, medium oil alkyd or long oil alkyd), an unsaturated polyester resin, a vinyl ester resin, an acrylate resin, an epoxy resin, a polyurethane resin, a polyaspartic acid resin, a phenolic binder, a silicone, a chlorinated rubber, a vinyl-based binder, polyvinyl alcohol, polyvinyl acetate, a saturated polyester binder, a polyacrylate, and an acrylate copolymer, a urea and a melamine resin, a silicate binder, a cellulose-based binder, and a silyl-modified polymer. Preferred binders comprise at least one of an alkyd resin (e.g., short oil alkyd, medium oil alkyd or long oil alkyd), an unsaturated polyester resin, a vinyl ester resin, an acrylate resin, an epoxy resin, a polyurethane resin, a polyacrylate and an acrylate copolymer, a polyaspartic acid resin, and a silyl-modified polymer.

[0086] Such binders may preferably be solvent-based binders, solventless binders or aqueous binders. Both solvent-based binders and aqueous binders can be supplied as solutions, emulsions or dispersions. Thus, the above-mentioned binders also include aqueous binder systems such as styrene acrylic dispersions, urethane acrylic dispersions and alkyd emulsions. The binder also includes a non-aqueous dispersion (NAD) system.

[0087] Another subject of the present invention is an article, wherein at least a part of the surface of the article is coated with the liquid composition. In a different embodiment, the coated article can be obtained by a process comprising providing an article, providing a liquid composition according to the present invention, and coating at least a part of the surface of the article with the liquid composition.

[0088] In addition, in yet another different embodiment, the present invention relates to a coated article, wherein at least a part of the surface of the article is coated with the liquid composition according to the present invention, and the liquid composition is cured. In another embodiment, the coated article can be obtained by a process comprising providing an article, providing a liquid composition according to the present invention, coating at least a part of the surface of the article with the liquid composition, and solidifying the liquid composition.

[0089] Suitable articles are any three-dimensional objects, regardless of their size and volume, and regardless of whether they are movable or stationary. Non-limiting examples for illustration include interior and exterior finishes of buildings, floors, furniture, vehicles used for transportation (such as automobiles, motorcycles, boats, airplanes, agricultural machinery, and all kinds of freight vehicles), bridges and tunnels, machinery and production equipment, electrical equipment, cans, metal coils, wires, containers, household goods and hardware, pulp and paper, and all kinds of articles made of wood, metal, plastic or glass (for example, for functional or ornamental purposes). The meaning of the term "coating" is well known to those skilled in the art. In this context, this term refers to applying a liquid composition to the surface or other areas of the article to cover the whole article at least partially or even in an enclosed state. In this case, the liquid composition is toughened or solidified after being applied to the article. Solidification means that the liquid composition is converted into a solid phase. This can be achieved by evaporation of the liquid diluent (physical drying) or chemical cross-linking reaction (curing), and by combinations thereof.

[0090] The present invention will be further described below with reference to examples. The selection of each reaction condition, such as reaction temperature, reaction time and metering supply rate, is known to those skilled in the art and will be described in more detail in the examples.

Examples

[0091] Experimental part Examples of the present invention Preparation of intermediates

[0092]

Table 1

[0093] Production of Intermediates I1 - I6:

[0094]

Table 2

[0095] The hydroxyl value was measured by acetylation of the free hydroxyl groups of the substance with acetic anhydride in a pyridine solvent. After completion of the reaction, water was added to convert the remaining unreacted acetic anhydride to acetic acid, which was then titrated with potassium hydroxide for measurement.

[0096] Procedures for Intermediates I1 - I6: 2 mol each of TDI T65 or TDI T80 and 200 ppm of benzoyl chloride were weighed into a glass flask equipped with a stirrer, reflux condenser, and nitrogen inlet, and heated to 40°C. Subsequently, 1 mol of monoalcohol (according to Table 2 above) was added little by little to the reaction mixture over 30 minutes. The reaction mixture was stirred at 60°C for an additional 5 hours. A clear pale yellow liquid intermediate containing excess diisocyanate was obtained. The excess diisocyanate contained in the intermediate was removed by distillation to obtain Intermediates I1 - I6.

[0097] Comparative Examples (Not according to the present invention) C1: In a four-necked flask equipped with a stirrer, 75.0 g of N-butylbutyrolactam was heated to 80°C with 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 little by little within 30 minutes while stirring so that the temperature did not exceed 85°C. Thereafter, the mixture was stirred at 80°C for 3 hours. As a result, a transparent yellowish product was obtained.

[0098] C2: In a four-necked flask equipped with a stirrer, 1.06 g of lithium chloride was added to 73.9 g of N-butylbutyrolactam while stirring. The mixture was heated to 80 °C under a nitrogen atmosphere. Lithium chloride was dissolved within 30 minutes while stirring. 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 portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Then, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0099] C3: In a four-necked flask equipped with a stirrer, 70.0 g of N-butylbutyrolactam was heated to 80 °C under a nitrogen atmosphere while stirring. 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 portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Then, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0100] C4: In a four-necked flask equipped with a stirrer, 1.27 g of lithium chloride was added to 68.7 g of N-butylbutyrolactam while stirring. The mixture was heated to 80 °C under a nitrogen atmosphere. Lithium chloride was dissolved within 30 minutes while stirring. 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 portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Then, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0101] C5: In a four-necked flask equipped with a stirrer, 70.0 g of N-butylbutyrolactam was heated to 80 °C under a nitrogen atmosphere. While stirring, 3.20 g of m-xylylenediamine (23.5 mmol) was added and the mixture was homogenized. 26.8 g of intermediate I4 (47.0 mmol) was added portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Thereafter, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0102] C6: In a four-necked flask equipped with a stirrer, 75.0 g of N-butylbutyrolactam was heated to 80 °C under a nitrogen atmosphere. While stirring, 4.21 g of m-xylylenediamine (30.9 mmol) was added and the mixture was homogenized. 30.8 g of intermediate I5 (61.8 mmol) was added portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Thereafter, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0103] C7: In a four-necked flask equipped with a stirrer, 1.25 g of lithium chloride was added to 63.8 g of N-butylbutyrolactam while stirring. The mixture was heated to 80 °C under a nitrogen atmosphere. Lithium chloride was dissolved within 30 minutes while stirring. While stirring, 4.21 g of m-xylylenediamine (30.9 mmol) was added and the mixture was homogenized. 30.8 g of intermediate I5 (61.8 mmol) was added portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Thereafter, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0104] C8: In a four-necked flask equipped with a stirrer, 65.0 g of N-butylbutyrolactam was heated to 80 °C under a nitrogen atmosphere while stirring. 3.92 g of m-xylylenediamine (28.8 mmol) was added and the mixture was homogenized. A mixture of 7.47 g of intermediate I1 (18.5 mmol) and 23.6 g of intermediate I2 (38.8 mmol) was added portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Thereafter, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent pale yellow product was obtained.

[0105] C9: In a four-necked flask equipped with a stirrer, 1.00 g of lithium chloride was added to 64.0 g of N-butylbutyrolactam while stirring. The mixture was heated to 80 °C under a nitrogen atmosphere. Lithium chloride was dissolved within 30 minutes while stirring. 3.92 g of m-xylylenediamine (28.8 mmol) was added and the mixture was homogenized. A mixture of 7.47 g of intermediate I1 (18.5 mmol) and 23.6 g of intermediate I2 (38.8 mmol) was added portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Thereafter, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent pale yellow product was obtained.

[0106] C10: In a four-necked flask equipped with a stirrer, 65.0 g of N-butylbutyrolactam was heated to 80 °C under a nitrogen atmosphere. While stirring, 3.92 g of m-xylylenediamine (28.8 mmol) was added and the mixture was homogenized. A mixture of 7.47 g of intermediate I6 (18.5 mmol) and 23.6 g of intermediate I2 (38.8 mmol) was added portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Thereafter, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent pale yellow product was obtained.

[0107] C11: In a four-necked flask equipped with a stirrer, 60.0 g of N-butylbutyrolactam was heated to 80 °C under a nitrogen atmosphere. While stirring, 4.48 g of m-xylylenediamine (32.9 mmol) was added 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 portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Thereafter, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent pale yellow product was obtained.

[0108] C12: In a glass flask equipped with a stirrer, a reflux condenser and a nitrogen inlet, 85.0 g of N-butylbutyrolactam was heated to 60 °C while 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 portionwise to the reaction mixture over 25 minutes. The reaction mixture was stirred at 80 °C for an additional 3 hours. A clear yellow liquid product was obtained.

[0109] C13: 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-butylbutyrolactam by stirring 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 homogeneous mixture of 13.7 g of intermediate I3 (30.0 mmol) and 0.126 g of hexamethylene diisocyanate (0.751 mmol) was added portionwise to the reaction mixture over 25 minutes. The reaction mixture was stirred at 80 °C for an additional 3 hours. A clear yellow liquid product was obtained.

[0110] C14: In a four-necked flask equipped with a stirrer, 1.25 g of lithium chloride was added to 53.8 g of N-butylbutyrolactam while stirring. The mixture was heated to 80 °C under a nitrogen atmosphere. Lithium chloride was dissolved within 30 minutes while stirring. 6.49 g of m-xylylenediamine (47.7 mmol) was added and the mixture was homogenized. 38.5 g of intermediate I1 (95.4 mmol) was added portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Then, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0111] C15: In a four-necked flask equipped with a stirrer, 75.0 g of N-methylcaprolactam was heated to 80 °C under a nitrogen atmosphere while stirring. 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 portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Then, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0112] C16: In a four-necked flask equipped with a stirrer, 70.0 g of N-methylcaprolactam was heated to 80 °C under a nitrogen atmosphere while stirring. 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 portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Then, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0113] C17: In a four-necked flask equipped with a stirrer, 75.0 g of N-ethylcaprolactam was heated to 80 °C under a nitrogen atmosphere while stirring. 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 portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Thereafter, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent pale yellow product was obtained.

[0114] C18: In a four-necked flask equipped with a stirrer, 70.0 g of N-ethylcaprolactam was heated to 80 °C under a nitrogen atmosphere while stirring. 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 portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Thereafter, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent pale yellow product was obtained.

[0115] C19: In a four-necked flask equipped with a stirrer, 75.0 g of N-cyclohexylpyrrolidone was heated to 80 °C under a nitrogen atmosphere while stirring. 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 portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Thereafter, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent pale yellow product was obtained.

[0116] C20: In a four-necked flask equipped with a stirrer, 70.0 g of N-cyclohexylpyrrolidone was heated to 80 °C under a nitrogen atmosphere while stirring. 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 portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Thereafter, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent pale yellow product was obtained.

[0117] Examples of the present invention E1: In a four-necked flask equipped with a stirrer, 30.0 g of ε-caprolactam was added to 45.0 g of N-butylbutyrolactam with stirring. The mixture was heated to 80 °C under a nitrogen atmosphere. The ε-caprolactam was dissolved within 30 minutes with stirring. 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 portionwise within 30 minutes with stirring so that the temperature did not exceed 85 °C. Then, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0118] E2: In a four-necked flask equipped with a stirrer, 28.0 g of ε-caprolactam was added to 21.0 g of N-butylbutyrolactam and 21.0 g of DMSO with stirring. The mixture was heated to 80 °C under a nitrogen atmosphere. The ε-caprolactam was dissolved within 30 minutes with stirring. 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 portionwise within 30 minutes with stirring so that the temperature did not exceed 85 °C. Then, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0119] E3: In a four-necked flask equipped with a stirrer, 28.0 g of ε-caprolactam was added to 28.0 g of N-butylbutyrolactam and 14 g of DMSO with stirring. The mixture was heated to 80 °C under a nitrogen atmosphere. The ε-caprolactam was dissolved within 30 minutes with stirring. 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 portionwise within 30 minutes with stirring so that the temperature did not exceed 85 °C. Then, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0120] E4: In a four-necked flask equipped with a stirrer, 28.0 g of ε-caprolactam was added to 42.0 g of N-butylbutyrolactam with stirring. The mixture was heated to 80 °C under a nitrogen atmosphere. The ε-caprolactam was dissolved within 30 minutes with stirring. 3.20 g of m-xylylenediamine (23.5 mmol) was added and the mixture was homogenized. 26.8 g of intermediate I4 (47.0 mmol) was added portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Then, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0121] E5: In a four-necked flask equipped with a stirrer, 28.0 g of ε-caprolactam was added to 28.0 g of N-butylbutyrolactam and 14.0 g of DMSO with stirring. The mixture was heated to 80 °C under a nitrogen atmosphere. The ε-caprolactam was dissolved within 30 minutes with stirring. 3.20 g of m-xylylenediamine (23.5 mmol) was added and the mixture was homogenized. 26.8 g of intermediate I4 (47.0 mmol) was added portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Then, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0122] E6: In a four-necked flask equipped with a stirrer, 26.0 g of ε-caprolactam was added to 39.0 g of N-butylbutyrolactam with stirring. The mixture was heated to 80 °C under a nitrogen atmosphere. The ε-caprolactam was dissolved within 30 minutes with stirring. 4.21 g of m-xylylenediamine (30.9 mmol) was added and the mixture was homogenized. 30.8 g of intermediate I5 (61.8 mmol) was added portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Then, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0123] E7: In a four-necked flask equipped with a stirrer, 26.0 g of ε-caprolactam was added to 39.0 g of N-butylbutyrolactam while stirring. The mixture was heated to 80 °C under a nitrogen atmosphere. ε-Caprolactam was dissolved within 30 minutes while stirring. 3.92 g of m-xylylenediamine (28.8 mmol) was added and the mixture was homogenized. A mixture of 7.47 g of intermediate I1 (18.5 mmol) and 23.6 g of intermediate I2 (38.8 mmol) was added portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Thereafter, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent pale yellow product was obtained.

[0124] E8: In a four-necked flask equipped with a stirrer, 26.0 g of ε-caprolactam was added to 39.0 g of N-butylbutyrolactam while stirring. The mixture was heated to 80 °C under a nitrogen atmosphere. ε-Caprolactam was dissolved within 30 minutes while stirring. 3.92 g of m-xylylenediamine (28.8 mmol) was added and the mixture was homogenized. A mixture of 7.47 g of intermediate I6 (18.5 mmol) and 23.6 g of intermediate I2 (38.8 mmol) was added portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Thereafter, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent pale yellow product was obtained.

[0125] E9: In a four-necked flask equipped with a stirrer, 24.0 g of ε-caprolactam was added to 36.0 g of N-butylbutyrolactam while stirring. The mixture was heated to 80 °C under a nitrogen atmosphere. ε-Caprolactam was dissolved within 30 minutes while stirring. 4.48 g of m-xylylenediamine (32.9 mmol) was added 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 portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Thereafter, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent pale yellow product was obtained.

[0126] E10: 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-butylbutyrolactam with stirring 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 homogeneous mixture of 13.7 g of intermediate I3 (30.0 mmol) and 0.126 g of hexamethylene diisocyanate (0.751 mmol) was added to the reaction mixture in small portions over 25 minutes. The reaction mixture was stirred at 80 °C for an additional 3 hours. A clear yellow liquid product was obtained.

[0127] E11: In a four-necked flask equipped with a stirrer, 21.5 g of ε-caprolactam and 1.25 g of LiCl were added to 32.3 g of N-butylbutyrolactam with stirring. The mixture was heated to 80 °C under a nitrogen atmosphere. The ε-caprolactam and LiCl were dissolved within 30 minutes with stirring. 6.49 g of m-xylylenediamine (47.7 mmol) was added and the mixture was homogenized. 38.5 g of intermediate I1 (95.4 mmol) was added in small portions within 30 minutes while stirring so that the temperature did not exceed 85 °C. Thereafter, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0128] E12: In a four-necked flask equipped with a stirrer, 26.3 g of ε-caprolactam was added to 48.8 g of N-methylcaprolactam with stirring. The mixture was heated to 80 °C under a nitrogen atmosphere. The ε-caprolactam was dissolved within 30 minutes with stirring. 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 in small portions within 30 minutes while stirring so that the temperature did not exceed 85 °C. Thereafter, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0129] E13: In a four-necked flask equipped with a stirrer, 24.5 g of ε-caprolactam was added to 45.5 g of N-methylcaprolactam with stirring. The mixture was heated to 80 °C under a nitrogen atmosphere. The ε-caprolactam was dissolved within 30 minutes with stirring. 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 portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Thereafter, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0130] E14: In a four-necked flask equipped with a stirrer, 26.3 g of ε-caprolactam was added to 48.8 g of N-ethylcaprolactam with stirring. The mixture was heated to 80 °C under a nitrogen atmosphere. The ε-caprolactam was dissolved within 30 minutes with stirring. 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 portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Thereafter, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0131] E15: In a four-necked flask equipped with a stirrer, 24.5 g of ε-caprolactam was added to 45.5 g of N-ethylcaprolactam with stirring. The mixture was heated to 80 °C under a nitrogen atmosphere. The ε-caprolactam was dissolved within 30 minutes with stirring. 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 portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Thereafter, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0132] E16: In a four-necked flask equipped with a stirrer, 22.5 g of ε-caprolactam was added to 52.5 g of N-cyclohexylpyrrolidone while stirring. The mixture was heated to 80 °C under a nitrogen atmosphere. The ε-caprolactam was dissolved within 30 minutes while stirring. 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 in small portions within 30 minutes while stirring so that the temperature did not exceed 85 °C. Thereafter, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0133] E17: In a four-necked flask equipped with a stirrer, 21.0 g of ε-caprolactam was added to 49.0 g of N-cyclohexylpyrrolidone while stirring. The mixture was heated to 80 °C under a nitrogen atmosphere. The ε-caprolactam was dissolved within 30 minutes while stirring. 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 in small portions within 30 minutes while stirring so that the temperature did not exceed 85 °C. Thereafter, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0134] E18: In a four-necked flask equipped with a stirrer, 2.5 g of pyrrolidin-2-one was added to 72.5 g of N-butylbutyrolactam while 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 in small portions within 30 minutes while stirring so that the temperature did not exceed 85 °C. Thereafter, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0135] E19: In a four-necked flask equipped with a stirrer, 5.0 g of pyrrolidin-2-one was added to 65.0 g of N-butylbutyrolactam with 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 portionwise within 30 minutes while stirring so that the temperature did not exceed 85 °C. Then, the mixture was stirred at 80 °C for 3 hours. As a result, a transparent yellowish product was obtained.

[0136] Storage stability 100 g of the examples of the present invention and Comparative Example 100 according to the present invention were stored at room temperature (23 °C) until visual changes became significant. Visual changes include gelation of the material and / or formation of precipitates.

[0137] [Table 3]

[0138] From Table 3, it can be seen that Examples E1 to E19 of the present invention have significantly increased storage stability compared to their corresponding Comparative Examples according to the present invention.

[0139] Application test

[0140] [Table 4]

[0141] Test 1: Whitening of aqueous two-component PU clear coat The production of the aqueous two-pack PU clear coat was carried out using the formulation shown in Table 5. All components of Component A were added to a PE beaker under stirring conditions and homogenized at room temperature (23 °C) for 10 minutes at 1000 rpm with a toothed plate of 4 cm in diameter using a Dispermat LC3 (VMA Getzmann). Then, the pH of Component A was adjusted with a DMEA solution (10% in water) to a pH of 8.2 - 8.5. 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 combined with a urea compound at a metered supply amount of 0.5% by weight (calculated based on the total clear coat) while stirring at 1500 rpm with a toothed plate of 2.5 cm in diameter using a Dispermat LC3 (VMA Getzmann) at room temperature (23 °C) for 5 minutes.

[0142] After storage overnight at room temperature, a curing agent solution was added at a specific mixing ratio and stirred with a spatula for homogenization. The sample was applied to glass using a frame film applicator (BYK-Gardner GmbH) to a wet film thickness of 120 μm and dried at room temperature for 1 week. For the whitening test, a household sponge (2 cm × 2 cm) immersed in water was placed on the lacquer coating film for 24 hours. Immediately after removing the sponge and drying, the whitening of the coating film was visually evaluated on a rating scale of 1 - 5 (1 = no whitening, 5 = significant whitening).

[0143]

Table 5

[0144] From Table 6, surprisingly, it can be seen that the application of Example E7 of the present invention has no effect on the whitening of the aqueous clear coat, while the application of Comparative Example C9 not according to the present invention causes a significant deterioration in whitening.

[0145] Test 2: Whitening of Solvent-Based Two-Pack PU Clear Coat The solvent-based two-pack PU clear coat was produced using the formulation in Table 7. All components of Component A were added to a PE beaker under stirring conditions and homogenized at room temperature (23°C) for 10 minutes at 1000 rpm with a toothed plate of 4 cm in diameter using a Dispermat LC3 (VMA Getzmann). Component A was divided into small portions (50 g in a 100 ml glass bottle), and the sample of the present invention was combined with a urea compound at a metered supply amount of 0.5% by weight (calculated based on the entire clear coat formulation) while stirring at 1500 rpm with a toothed plate of 2.5 cm in diameter using a Dispermat LC3 (VMA Getzmann) at room temperature (23°C) for 5 minutes.

[0146] After storing overnight at room temperature, a curing agent was added at a specific mixing ratio and homogenized by stirring with a spatula. The sample was applied to glass using a frame film applicator (BYK-Gardner GmbH) to give a wet film thickness of 120 μm and dried at room temperature for 1 week. A water immersion test was carried out for whitening evaluation. In this test, the drawdown was placed in a water bath of type 1004 (Gesellschaft fuer Labortechnik mbH) at 60°C for 1 week. Immediately after taking the sample out of the bath and drying it, the whitening of the lacquer film was visually evaluated on an evaluation scale of 1 - 5 (1 = no whitening - 5 = significant whitening).

[0147]

Table 6

[0148] From Table 8, it was found that the application of Example E1 of the present invention did not affect the whitening of the solvent-based clear coat, while the application of Comparative Example C2 not according to the present invention caused a significant deterioration in whitening.

[0149] Test 3: Sag resistance in thermoplastic acrylic clear coat The production of the thermoplastic acrylic clear coat was carried out using the formulation shown in Table 9. All the components were added to a PE beaker under stirring conditions and homogenized at room temperature (23 °C) for 15 minutes at 1000 rpm with a toothed plate of 4 cm in diameter using a Dispermat LC3 (VMA Getzmann). The clear coat was divided into small portions (50 g in a 100 ml glass bottle), and the sample of the present invention was combined with the urea compound at a metered supply amount of 0.75 wt% and 1.0 wt% (calculated based on the total clear coat) while stirring at 1500 rpm with a toothed plate of 2.5 cm in diameter using a Dispermat LC3 (VMA Getzmann) at room temperature (23 °C) for 5 minutes. After storage overnight at room temperature, the sample was applied using a 421 / S type stepped doctor blade (Erichsen GmbH & Co KG) for the sag resistance test, and the wet film thickness was set to 50 - 500 μm or 550 - 1000 μm. This application was carried out at a application speed of 50 mm / s using an automatic applicator byko - drive XL (BYK - Gardner GmbH) on a contrast card 2801 (BYK - Gardner GmbH). Immediately after application, the draw - down was vertically suspended at room temperature until it dried. After drying, a visual evaluation of the sag resistance was performed. As a result, for the wet film thickness, it was considered that after drying, the draw - down showed a distinct separation, there were no runners, and no bulges occurred between the applied film thicknesses.

[0150]

Table 7

[0151] From Table 10, it can be seen that the application of Example E1 of the present invention shows better sag resistance in the thermoplastic acrylic clear coat than the application of Example C2 not according to the present invention.

[0152] Test 4: Gel Strength and Turbidity in Various Solvents A 100-ml glass bottle was filled with 50 g of various solvents according to Table 11. The sample of the present invention was combined with a urea compound at a metered supply amount of 1.0% by weight (calculated based on the amount of the solvent) while stirring at 1500 rpm with a toothed plate having a diameter of 2.5 cm at room temperature (23°C) for 5 minutes using a Dispermat LC3 (VMA Getzmann). After storage overnight at room temperature (23°C), the sample was evaluated for gel strength and turbidity. The visual evaluation of gel strength can range from a distinct gel to no gel (evaluation scale 1 (distinct gel) to 5 (no gel)), and the visual evaluation of turbidity can range from no turbidity to distinct turbidity (scale 1 (no turbidity) to 5 (distinct turbidity)).

[0153]

Table 8

[0154] From Table 12, it can be concluded that Examples E1, E2, E3, E6, E7, and E11 of the present invention provide better gel strength than Comparative Examples C2, C4, C7, C9, and C14 in each solvent.

[0155]

Table 9

[0156] From Table 13, it can be concluded that the administration examples including Examples E1, E2, E3, E6, E7, and E11 of the present invention show lower turbidity than Examples C2, C4, C7, C9, and C14 not according to the present invention in each solvent.

[0157] Test 5: Rheological Effects in Various Oils and Very Low-Polarity Solvents A 100 ml glass bottle was filled with 50 g of various oils or very low-polarity solvents according to Table 14. The sample of the present invention was combined with a urea compound at a metered supply amount of 1.0% by weight (calculated based on the amount of oil / solvent) while stirring at 1500 rpm with a toothed plate having a diameter of 2.5 cm using a Dispermat LC3 (VMA Getzmann) at room temperature (23°C) for 5 minutes. After storing overnight at room temperature, the sample was evaluated for gel strength. The visual evaluation of gel strength ranges from a distinct gel (1) to no gel (5).

[0158]

Table 10

[0159] From Table 15, it can be seen that Example E10 of the present invention exhibits better gel strength than Comparative Example C13 not according to the present invention in each oil and low-polarity solvent.

Claims

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

2. The composition according to claim 1, wherein the solvent contains at least one of an N-substituted cyclic amide, an acyclic dialkylamide of a monofunctional and bifunctional carboxylic acid, and a sulfoxide.

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

4. The composition according to any one of claims 1 to 3, wherein the cyclic amide has a molecular weight of 71 to 250 g / mol.

5. The composition according to any one of claims 1 to 4, wherein the cyclic amide contains at most 2 amide groups.

6. The composition according to any one of claims 1 to 5, wherein the cyclic amide contains at least one of ε-caprolactam, γ-butyrolactam, δ-valerolactam, and mixtures thereof.

7. The composition according to any one of claims 1 to 6, wherein the urea compound is a urea urethane.

8. The composition according to any one of claims 1 to 7, wherein the urea compound contains at least 2 urea groups and at least 2 urethane groups.

9. The composition according to any one of claims 1 to 8, wherein the urea compound has a number average molecular weight of 400 g / mol to 30,000 g / mol.

10. The composition according to any one of claims 1 to 9, wherein the composition is liquid at 25 °C and 1013 mbar.

11. The composition according to any one of claims 1 to 10, wherein the composition contains 0.1 to 15.0% by weight of a salt, calculated based on the total weight of the cyclic amide, the at least one solvent, the urea compound, and the salt.

12. When the composition is calculated based on the total weight of the cyclic amide, the solvent, and the urea compound, 1 to 60% by weight of the cyclic amide containing at least one amide NH group; 5 to 70% by weight of a solvent different from the cyclic amide containing the at least one amide NH group, wherein the solvent contains at least one of a dialiphatic-substituted amide group and a sulfoxide group, and 5 to 60% by weight of a urea compound having a number average molecular weight of at least 350 g / mol The composition according to any one of claims 1 to 11, comprising.

13. Use of the composition according to any one of claims 1 to 12 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 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 part of the surface of the article is coated with the liquid composition according to claim 14.

Images