EP4638538A1 - Agent de régulation de rhéologie liquide - Google Patents

Agent de régulation de rhéologie liquide

Info

Publication number
EP4638538A1
EP4638538A1 EP23837223.9A EP23837223A EP4638538A1 EP 4638538 A1 EP4638538 A1 EP 4638538A1 EP 23837223 A EP23837223 A EP 23837223A EP 4638538 A1 EP4638538 A1 EP 4638538A1
Authority
EP
European Patent Office
Prior art keywords
mol
group
molecular weight
urea
aliphatic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP23837223.9A
Other languages
German (de)
English (en)
Inventor
Florian FRIESE
Nico HEITZER
Alexander GERS-BARLAG
René NAGELSDIEK
Christiane KNAPPKE-BONGARTZ
Sylvia Bühne
André TIEMANN
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BYK Chemie GmbH
Original Assignee
BYK Chemie GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BYK Chemie GmbH filed Critical BYK Chemie GmbH
Publication of EP4638538A1 publication Critical patent/EP4638538A1/fr
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
    • C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
    • C08G18/0847—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of solvents for the polymers
    • C08G18/0852—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of solvents for the polymers the solvents being organic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
    • C08G18/2825—Alkanols, cycloalkanols or arylalkanols including terpenealcohols having at least 6 carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
    • C08G18/2835—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds having less than 5 ether groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3225—Polyamines
    • C08G18/3237—Polyamines aromatic
    • C08G18/324—Polyamines aromatic containing only one aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
    • C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/8064—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/02—Polyureas

Definitions

  • the invention relates to a composition
  • a composition comprising a liquid carrier which is liquid at a temperature of 20° C, a component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group, dissolved in the liquid carrier, and a urea compound having a molecular weight below 350 g/mol dissolved in the liquid carrier. It further relates to the use of the composition for controlling the rheology of a liquid composition, a liquid composition, and a coated article.
  • the system properties are usually improved with respect to sag resistance, improved storage stability (due to reduced settling of solid particles), or a general increase in viscosity, often referred to as “thickening”.
  • the rheology of liquid systems is often controlled using clays, e. g., bentonites, and/or silicas, which may optionally be organically modified, hydrogenated castor oil, and polyamide waxes.
  • clays e. g., bentonites, and/or silicas, which may optionally be organically modified, hydrogenated castor oil, and polyamide waxes.
  • a disadvantage of these rheology control auxiliaries is that they are mostly dry solids, which must be processed to a semi-finished form using solvents and shear forces, and/or introduced into the liquid system by means of targeted temperature control.
  • Non-observance of these temperatures and/or appropriate incorporation conditions can lead not only to poor rheological performance, but also to detrimental properties of the products.
  • these rheology control auxiliaries frequently lead to instances of clouding and haze in clear, transparent coatings.
  • operating with dry, powderous products, which cause dusts during processing may be technologically unfavorable.
  • a liquid application alternative to these rheology control auxiliaries is provided by solutions of particular urea components as described for example in EP 1188779 A.
  • ionic liquids can be used as described in DE 102008059702 A.
  • a further aspect which should be noted in connection with rheology control auxiliaries provided in liquid form, is the storage stability thereof. For instance, prolonged storage times or elevated storage stress, for example in the case of storage with temperature variations, can lead to reduced storage stability, accompanied by reduced efficacy in the target systems. Therefore, it is desirable that rheology control auxiliaries have a good storage stability and will not easily precipitate or gelate on storage. To prevent early precipitation on storage from happening, small amounts of salts, especially halides such as LiCl are usually added, which act as a stabilizer.
  • salts also give rise to numerous issues in application performance, especially in the case of halides such as LiCl
  • these ionic compounds have negative effects on properties such as influence on corrosion caused by the coating system, resistance of the coated material against environmental effects, discoloration, whitening, pollution, or conductivity. All these parameters mentioned above limit the choice of adequate preparations.
  • suitable rheology control auxiliaries is therefore difficult since these especially have to be compatible with the later application systems and need to comply with a multiplicity of requirements. They have to show not only an improved rheological activity in the application system, but also a broad compatibility in application-relevant formulations. There is still an ongoing need to provide improved rheology additives.
  • the improved rheology additive should lead to very reliable and increased thickening effects in various formulations while storage stability of these rheology control auxiliaries needs to be favorable. Moreover, the rheology additive should show a reduced influence on the discoloration of the application system, for example when added to a clear coat.
  • Another object of the invention was to provide a rheology control agent that leads to an improved storage stability and a further object of the invention is to provide a rheology control agent which is essentially devoid of salts. Another object of the invention was to provide a rheology control agent, which leads to lesser discoloration when incorporated into the application system.
  • a composition comprising a liquid carrier which is liquid at a temperature of 20 °C, a component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group, dissolved in the liquid carrier, and a urea compound having a molecular weight below 350 g/mol dissolved in the liquid carrier.
  • the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group comprises a urea- urethane-compound.
  • the component comprises molecules containing at least one urea group and at least one urethane group. In another embodiment, the component comprises molecules containing at least one urea group and at least two urethane groups. In another embodiment, the component comprises molecules containing at least two urea groups; in a different embodiment the component comprises two urea and two urethane groups; in yet another embodiment, the component comprises molecules containing at least four urea or more than four urea groups. In a different embodiment, the component comprises molecules containing at least two urea groups and at least two urethane groups. In a different embodiment of the invention, urethane groups may even be absent.
  • urea-based compounds 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 1396510 A1 are employed.
  • a preferred class of the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group can be described according to the following general formula (U-1) R31-[R33-Z-R34-W-] n -R32 (U-1) where R31 and R32 independently of one another and independently of each occurrence represent a branched or unbranched, saturated or unsaturated organic group which contains 1 to 100 carbon atoms and which has not more than one urea group each and not more than one urethane group each, R33 and R34 independently of one another and independently of each occurrence represent branched or unbranched polyester groups containing 1 to 300 carbon atoms and optionally containing ether groups, branched or unbranched polyether groups
  • the component is selected from the general formulas (U- 2a), (U-2b), (U-2c), (U-2d), and (U-2e).
  • AM is selected from a linear or branched, saturated or unsaturated, aliphatic, cycloaliphatic, aromatic or aliphatic-aromatic organic group having 2 to 50 C atoms
  • AM is independently selected from a linear or branched, saturated or unsaturated, aliphatic, cycloaliphatic, aromatic or aliphatic-aromatic organic group having 2 to 50 C atoms
  • AM1 and AM2 independently of one another and independently in case of multiple occurrences represent a linear or branched, saturated or unsaturated, aliphatic, aromatic or aliphatic-aromatic organic group having 1 to 50 C atoms
  • IC1 and IC2 independently of one another and independently in case of multiple occurrences represent a linear or branched, saturated or unsaturated, aliphatic, aromatic or aliphatic or aromatic or
  • RP1 and RP2 independently of one another and independently in case of multiple occurrences 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
  • 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 optional
  • the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group has a structure according to formula (U-2a) in which RP1 is selected from a hydrocarbyl group having 4 to 24 carbon atoms or a polyether segment having up to 50 alkylene oxide repeating units, preferably a segment Q-(O-AO) r in which Q is a C1 to C18 alkyl or alkenyl group, AO is a group C2H4 or C3H6 and r is an integer of 2 to 35, IC1 and IC2 are preferably selected from one of the following bivalent groups (with “*” indicating the connection sites) .
  • AM is selected from a group C 2 H 4 , C 3 H 6 , C 4 H 8 , C 5 H 10, C 6 H 12 , C 6 H 10, –CH 2 -C 6 H 4 -CH 2 - or a group in which Rx and Ry represent H or CH3.
  • IC1 and/or IC2 are selected from Even more preferably, IC1 and IC2 are selected from
  • AM is selected from C 2 H 4 and –CH 2 -C 6 H 4 -CH 2 - .
  • m is an integer from 0 to 10. In a special embodiment, m is an integer from 1 to 5.
  • the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group has a structure according to formula (U-2b) in which the 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 a linear or branched, saturated or unsaturated C1 to C24 alkyl or alkenyl group or a group C6H5-CH2- , and 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 comprising 1 to 30 ethylene oxide and/or propylene oxide based repeating units.
  • formula (U-2b) in which the preferred embodiments of IC1 and IC2 are as described for (U-2a), in particular a group C
  • q is an integer from 0 to 15, even more preferably from 0 to 7 and most preferably from 0 to 4, like from 1 to 4.
  • At least 50 wt. % of the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group have a structure according to formula (U-2a) or (U-2c).
  • at least 50 wt. % of all components having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group have a structure according to formula (U-2a) and m is 0 or m is 1 to 5; very preferably, m is 0.
  • the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group is a urea urethane and 95 – 100% by weight of the component contain at least one molecule 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, in case of multiple occurrences of Y1, Y1 independently represents a saturated or unsaturated, branched or unbranched hydrocarbon group containing 6 to 20 carbon atoms and in each case contains no molecule 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.
  • Y2 independently represents a saturated or unsaturated, branched or unbranched hydrocarbon group containing 6 to 20 carbon atoms.
  • the synthesis of the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group may suitably take place directly in the presence of the liquid carrier and the urea compound having a molecular weight below 350 g/mol.
  • the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group is synthesized in the presence of the liquid carrier and the urea compound having a molecular weight below 350 g/mol is added afterwards.
  • the component is synthesized in the presence of the urea compound having a molecular weight below 350 g/mol and the liquid carrier is added afterwards.
  • the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group is synthesized in the presence of the urea compound having a molecular weight below 350 g/mol and the liquid carrier, and a second liquid carrier different from the first one is added afterwards.
  • the component having at least one urea group has a number average molecular weight of from 400 g/mol to 30000 g/mol.
  • the component has a number average molecular weight (Mn) of at least 400 g/mol, preferably at least 500 g/mol.
  • the number average molecular weight is above 600 g/mol, even more preferably above 650 g/mol, and most preferably above 800 g/mol.
  • the number average molecular weight (Mn) of the component is preferably below 20000 g/mol, more preferably below 10000 g/mol, and most preferably below 8000 g/mol.
  • the number average molecular weight (Mn) is in the range of 650 g/mol to 20000 g/mol, more preferably in the range of 800 g/mol to 8000 g/mol, even more preferably in the range of 800 g/mol to 5000 g/mol.
  • the number average molecular weight is at least 800 g/mol, preferably 1000 g/mol, preferably at least 1500 g/mol, preferably in the range of 1500 g/mol to 20000 g/mol and more preferred in the range of 1500 g/mol to 8000 g/mol and even more preferred 1500 to 5000 g/mol.
  • the number and weight average molecular weights can be determined by gel permeation chromatography (eluent: solution of lithium bromide (content 5 g/l) in dimethylacetamide, standard: polymethylmethacrylate, column temperature: 50 °C) according to DIN EN ISO 13885-2 (November 2021). Alternatively, the number average molecular weight may be determined by calculation.
  • the number average molecular weight for small molecules up to 1000 g/mol may be determined by other methods such as mass spectroscopy or nuclear magnetic resonance spectroscopy.
  • the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group, dissolved in the liquid carrier is not cross-linked.
  • a typical example of cross-linked components are elastomers. It is preferred that the component having at least one urea group does not contain any cross-linked sections, furthermore it is preferred that the component is not an elastomer or comprises elastomers.
  • the composition according to the invention comprises a liquid carrier which is liquid at a temperature of 20 °C and 1013 mbar.
  • the liquid carrier comprises at least one of 1-(2-hydroxyethyl)-2- pyrrolidone, N,N-dimethyl lactamide (2-hydroxy-N,N-dimethylpropanamide) or a polar aprotic solvent. It is more preferred that the liquid carrier is a polar aprotic solvent.
  • the liquid carrier comprises a compound having at least one of a N-substituted amide group, and a sulfoxide group.
  • the liquid carrier 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, in this case the amide group cannot be an NH amide group.
  • the liquid carrier suitably comprises at least one of a N-substituted cyclic amide, non-cyclic dialkyl amide of mono- and difunctional carboxylic acids, N-acyl morpholines, and sulfoxides.
  • Suitable liquid carriers are for example N-substituted cyclic amides: N-alkyllactams, preferably N-alkyl butyrolactams, N-alkyl valerolactams, and N-alkyl caprolactams, wherein the alkyl groups suitably have 1 to 18 carbon atoms, more preferably 1 to 12 carbon atoms, even more preferably 1 to 8 carbon atoms), as well as hydroxyalkyllactams (e.g., hydroxyethylpyrrolidone) and N-cycloalkyllactams.
  • Cyclic amides are amides wherein the amide nitrogen and amide carbonyl carbon are part of the cyclic structure.
  • N-alkylbutyrolactams are N-methylbutyrolactam, N-ethylbutyrolactam, N-butylbutyrolactam, N-octylbutyrolactam and N-hydroxyethyl butyrolactam.
  • N- cyclohexylbutyrolactam is a further suitable example.
  • Suitable examples of N-substituted caprolactams are N-ethyl caprolactam, N-methyl caprolactam, N-butyl caprolactam, N-propyl caprolactam.
  • Non-cyclic dialkyl amides of mono- and difunctional carboxylic acids are non-cyclic dialkyl amides of mono- 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 comprise hydroxyl, ether or ester groups, such as N,N-dialkylamidoalkylesters, N,N-dialkylamidoalkyl ethers, N,N-dialkyllactamides.
  • Sulfoxides are suitable as well, preferably dimethyl sulfoxide.
  • Non-cyclic amides are amides wherein the amide nitrogen and amide carbonyl carbon are not both part of the cyclic structure.
  • N-formylmorpholine is considered to be a non-cyclic amide.
  • suitable liquid carriers are non-cyclic amides that are available from reaction of diamines and monocarboxylic acids. Suitable examples are reaction products of C1 to C18 monocarboxylic acids and C2 to C12 alkylene diamines.
  • Suitable liquid carriers 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-dialkylamidoalkylesters, N,N- dialkylamidoalkyl ethers, and acylmorpholines.
  • Preferred examples of these are also N,N-dimethylamidoalkyl ester, N,N-dimethylamidoalkyl ether, N-formylmorpholine and N-acetylmorpholine.
  • liquid carriers are N-acetyl caprolactam, epsilon-caprolactam, and 2- pyrrolidone; preferably, they are used in combination with at least one further carrier comprising at least one of an amide group and a sulfoxide group.
  • the composition according to the invention comprises a urea compound having a molecular weight below 350 g/mol dissolved in the liquid carrier.
  • the composition comprises the urea compound having a molecular weight below 350 g/mol in an amount in the range of 0.05 to 15.00 weight %, calculated on the total weight of the composition.
  • the composition comprises the urea compound in an amount in the range of 0.1 to 10.0 weight %, even more preferably 0.2 to 8.0 weight % and most preferably 0.25 to 7.00 weight %, calculated on the total weight of the composition, such as 0.3 to 6.0 weight % or 0.4 to 5.0 weight %
  • the composition comprises the urea compound having a molecular weight below 350 g/mol in an amount of less than 40 weight %, calculated on the total weight of the composition.
  • R1, R2 and R3 independently represent an organic group or hydrogen with the proviso that at least one of R1, R2 and R3 is an organic group.
  • R1, R2 and R3 independently represent an organic group or hydrogen with the proviso that R1 and R2 are linked to each other.
  • R1, R2 and R3 independently represent an organic group.
  • two of the groups R1, R2, and R3 independently represent an organic group, while the third group represents hydrogen.
  • R1 and R2 independently represent an organic group, while R3 represents hydrogen.
  • R2 and R3 independently represent an organic group, while R1 represents hydrogen.
  • R1 represents an organic group, while R2 and R3 represent hydrogen.
  • the urea compound having a molecular weight below 350 g/mol contains one urea group.
  • the organic groups may comprise 1 to 8 carbon atoms. More suitably the organic groups may comprise 1 to 4 carbon atoms and most suitably 1 to 2 carbon atoms.
  • R1, R2, and R3 independently represent an organic group, while the third group represents hydrogen.
  • R1 and R2 independently represent an organic group, while R3 represents hydrogen.
  • R2 and R3 independently represent an organic group, while R1 represents hydrogen.
  • R1 represents an organic group
  • R2 and R3 represent hydrogen
  • R1, R2 and R3 are independently organic groups consisting of the elements carbon and hydrogen having 1 to 8 carbon atoms, or hydrogen with the proviso that at least one of R1, R2 and R3 is an organic group.
  • R1, R2 and R3 are independently organic groups consisting of the elements carbon and hydrogen having 1 to 8 carbon atoms.
  • the organic groups consisting of the elements carbon and hydrogen consist of 1 to 4 carbon atoms and most suitably of 1 to 2 carbon atoms.
  • the urea compound having a molecular weight below 350 g/mol comprises at least one of 2-imidazolidinone, 1,3-dimethyl urea, 1-(2-hydroxyethyl)imidazolidin-2-one,1- methyl urea, urea, biuret, N,N'-diethylurea, 1,1-dimethylurea, N-ethylurea, 1,3-diphenylurea, N-phenylurea, N-butylurea, 1,1-diethylurea, N-tert-butylurea, 3-methyl-1,1-diphenylurea, 1,1- dimethyl-3-phenylurea, N,N′-dicyclohexylurea, benzoyleneurea, N,N′-trimethyleneurea, or glycoluril.
  • the urea compound having a molecular weight below 350 g/mol comprises at least one of 2-imidazolidinone, 1,3-dimethyl urea, 1-(2-hydroxyethyl)imidazolidin-2-one,1- methyl urea, urea or biuret. It is preferred that the urea compound has a molecular weight from 55 to 349 g/mol. It is more preferred that the urea compound has a molecular weight from 55 to 310 g/mol. It is most preferred that the urea compound has a molecular weight from 55 to 280 g/mol, such as 55 to 250 g/mol.
  • the urea compound has a molecular weight from 72 to 349 g/mol. It is more preferred that the urea compound has a molecular weight from 72 to 310 g/mol. It is most preferred that the urea compound has a molecular weight from 72 to 280 g/mol, such as 72 to 250 g/mol. In another embodiment, it is preferred that the urea compound has a molecular weight from 84 to 349 g/mol. It is more preferred that the urea compound has a molecular weight from 84 to 310 g/mol. It is most preferred that the urea compound has a molecular weight from 84 to 280 g/mol, such as 84 to 250 g/mol.
  • the urea compound has a molecular weight from 84 to 200 g/mol or from 84 to 150 g/mol.
  • the urea compound having a molecular weight below 350 g/mol and the liquid carrier are preferably present in the composition in a weight ratio from 1 : 5 to 1 : 200. More preferably in a weight ratio from 1 : 7 to 1 : 150 and even more preferred from 1 : 8 to 1: 140, such as 1 : 10 to 1 : 120 , such as 1 : 12 to 1 : 80, or 1 : 12 to 1 : 50.
  • the amount of urea compound having a molecular weight below 350 g/mol compared to the total weight of urea compound having a molecular weight below 350 g/mol and liquid carrier is at least 0.5 % by weight, preferably at least 0.6 % by weight, more preferably at least 0.7% by weight, even more preferably at least 0.8 % by weight, such as at least 1.2 % by weight or at least 1.5 % by weight.
  • the amount of urea compound having a molecular weight below 350 g/mol compared to the total weight of urea compound having a molecular weight below 350 g/mol and liquid carrier is at most 20.0 % by weight, preferably at most 14 % by weight, more preferably at most 12 % by weight, and at most 10 % by weight, such as at most 8 % by weight.
  • the amount of urea compound compared to the total weight of the urea compound having a molecular weight below 350 g/mol and liquid carrier is in the range of 0.5 % by weight to 20 % by weight, more suitably in the range of 0.7 % by weight to 14 % by weight, even more suitably 0.8 % by weight to 12 % by weight and most suitably 1.2 % by weight to 10 % by weight.
  • the amount of urea compound having a molecular weight below 350 g/mol compared to the total weight of the urea compound and liquid carrier is in the range of 1.5 % by weight to 8 % by weight.
  • the weight ratio of the urea compound having a molecular weight below 350 g/mol and the component having a number average molecular weight Mn is in the range of 400 g/mol to 30000 g/mol and having at least one urea group is suitably from 1 : 2 to 1 : 100, more suitably from 1 : 3 to 1 : 80 and most suitably from 1 : 4 to 1 : 60, such as 1 : 5 to 1 : 40.
  • the composition is a liquid at 23 °C and 1013 mbar.
  • the composition may comprise one or more salts.
  • the salts according to the present invention suitably comprise cations of elements of the main groups I and II of the Periodic Table of the Elements (alkali and alkaline earth metals) or ammonium ions and mixtures thereof.
  • Preferred salts are such containing lithium, calcium or magnesium, particularly preferably lithium and calcium cations, preferably in chloride, acetate, and/or nitrate form.
  • the salts contain as anions preferably monovalent anions, particularly preferably halides, pseudohalides, formate, acetate and/or nitrate, most particularly preferably chloride, acetate and/or nitrate.
  • the salts described herein generally do not have surface active properties. Salts having surface active properties fall under the definition of surfactants as described below.
  • salts are inorganic lithium salts, such as lithium chloride or lithium nitrate, as well as ammonium salts.
  • the composition suitably comprises from 0.01 to 15.00 weight-% of a salt, calculated on the total weight of the liquid carrier, the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group, the urea compound, and the salt.
  • the composition comprises 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.
  • the composition does not comprise a salt selected from lithium salts and halide salts or comprises such salts in low amounts.
  • Low amounts are salt amounts that do not exceed 1.0% by weight, and it is more preferred that the amount does not exceed 0.5 % by weight, and it is more preferred that the amount does not exceed 0.3 % by weight, preferably not exceed 0.1 % by weight, calculated on the weight of the composition.
  • the composition does not comprise a salt. If the composition does not comprise a salt, it is preferred that the salt content does not exceed 0.50 % by weight, and it is more preferred that is does not exceed 0.30 % by weight, preferably not exceed 0.10 % by weight, for example not exceed 0.05% by weight, calculated on the weight of the composition.
  • the composition does not comprise a salt but a surfactant.
  • the composition does not comprise a salt but comprises at least one of a surfactant and an ionic liquid.
  • the composition further comprises a surfactant.
  • the salt in the composition may be substituted by surfactants.
  • the surfactants may preferably substitute the salt completely or may be added in addition to salt. In the latter case, the surfactant may substitute the salt partially which leads to a reduced salt content, or the surfactant may be added in addition to the salt and the salt content remains unreduced.
  • Suitable surfactants are anionic surfactants, e.
  • sulfosuccinates alk(en)yl sulfates, alk(en)yl ether sulfates, ester sulfonates, soaps, ether carboxylic acids; nonionic surfactants, e. g., alcohol alkoxylates, alkylglycosides, fatty acid ester alkoxylates, amine oxides, gemini surfactants; cationic surfactants, e. g., alkyl ammonium salts, such as tetraalkyl ammonium salts, quaternary ammonium salts, esterquats; amphoteric or zwitterionic surfactants, e.
  • nonionic surfactants e. g., alcohol alkoxylates, alkylglycosides, fatty acid ester alkoxylates, amine oxides, gemini surfactants
  • cationic surfactants e. g., alkyl ammonium salts
  • the surfactants are employed in amounts 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, such as 1.0 to 10.0 % by weight, calculated on the total weight of the composition.
  • the composition further comprises an ionic liquid.
  • Ionic liquids have a relatively high molecular weight and also an ionogenic character and hence are generally substantially or completely involatile and therefore can be regarded as free of volatile organic compounds.
  • the term “ionic liquids” herein is to be understood as meaning organic salts or mixtures of organic salts which are liquid at room temperature (23° C) and 1013 mbar, wherein organic salts as well as salts in general are solid at 23 °C and 1013 mbar and have a crystal structure.
  • the cations of the ionic liquids used are preferably based on ammonium, pyridinium, pyrrolidinium, pyrrolium, oxazolium, oxazolinium, imidazolium, thiazolium or phosphonium ions and also mixtures thereof. Particular preference is given to cations based on imidazolium and oxazolium ions.
  • the anions are preferably selected from alkylsulfates, arylsulfates, sulfate, hydrogensulfate, phosphate, alkylphosphates, arylphosphates, tosylates, alkylborates, haloborates such as tetrafluoroborate for example, haloaluminates such as tetrachloroaluminate for example, carboxylates such as acetate and trifluoroacetate for example, perchlorate and also mixtures thereof.Alkylsulfates, tosylates and acetates are particularly preferred.
  • the composition comprises at least one ionic liquid having a cation selected from imidazolium and oxazolium, and having an anion selected from alkylsulfates, tosylates, tetrafluoroborates, and acetates.
  • the composition comprises 0.05 – 40.00 weight-% of the urea compound having a molecular weight below 350 g/mol, 5.00 – 90.00 weight-% of the liquid carrier, 5.00 – 60.00 weight-% of the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group, dissolved in the liquid carrier calculated on the total weight of the urea compound having a molecular weight below 350 g/mol, the liquid carrier and the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group.
  • the composition comprises 0.1 – 15.0 weight-% of the urea compound having a molecular weight below 350 g/mol, 10.0 – 90.0 weight-% of the liquid carrier, 5.0 – 60.0 weight-% of the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group, dissolved in the liquid carrier calculated on the total weight of the urea compound having a molecular weight below 350 g/mol, the liquid carrier and the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group.
  • the composition comprises 0.2 – 12.0 weight-% of the urea compound having a molecular weight below 350 g/mol, 20.0– 90.0 weight-% of the liquid carrier, 7.0 – 55.0 weight-% of the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group, dissolved in the liquid carrier calculated on the total weight of the urea compound having a molecular weight below 350 g/mol, the liquid carrier and the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group.
  • the composition comprises 0.3 – 10.0 weight-% of the urea compound having a molecular weight below 350 g/mol, 25.0– 90.0 weight-% of the liquid carrier, 9.7 – 50.0 weight-% of the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group, dissolved in the liquid carrier calculated on the total weight of the urea compound having a molecular weight below 350 g/mol, the liquid carrier and the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group.
  • the composition comprises 0.4 – 9.0 weight-% of the urea compound having a molecular weight below 350 g/mol, 30.0– 85.0 weight-% of the liquid carrier, 14.6 – 45.0 weight-% of the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group, dissolved in the liquid carrier calculated on the total weight of the urea compound having a molecular weight below 350 g/mol, the liquid carrier and the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group.
  • the composition comprises 0.5 – 8.0 weight-% of the urea compound having a molecular weight below 350 g/mol, 35.0– 84.5 weight-% of the liquid carrier, 15.0 – 40.0 weight-% of the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group, dissolved in the liquid carrier calculated on the total weight of the urea compound having a molecular weight below 350 g/mol, the liquid carrier and the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group.
  • the composition comprises 0.7 – 7.5 weight-% of the urea compound having a molecular weight below 350 g/mol, 50.0– 80.0 weight-% of the liquid carrier, 15.0 – 40.0 weight-% of the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group, dissolved in the liquid carrier calculated on the total weight of the urea compound having a molecular weight below 350 g/mol, the liquid carrier and the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group.
  • the composition comprises at least two liquid carriers different from each other, with the proviso that one of the liquid carriers is dimethyl sulfoxide (DMSO) and the second liquid carrier is a liquid carrier comprising at least one of a di-aliphatic-substituted amide group.
  • DMSO dimethyl sulfoxide
  • the weight amount of DMSO compared to the total weight of DMSO, the second liquid carrier comprising at least one of a di-aliphatic-substituted amide group is at least 1%, preferably at least 2%, more preferably at least 5%, even more preferably at least 7%, most preferably at least 10%.
  • the weight amount of DMSO compared to the total weight of DMSO, the second liquid carrier comprising at least one of a di-aliphatic-substituted amide group is at most 60%, preferably at most 50%, more preferably at most 45%, even more preferably at most 40%, most preferably at most 35%, such as at most 30%.
  • the invention deals with the use of the composition for controlling the rheology of a liquid composition.
  • the term “liquid composition” according to the present invention denotes a composition, being liquid at 23 °C and 1013 mbar.
  • the composition of the present invention may be employed to control the rheology of various kinds of liquid compositions. Therefore, in one embodiment, the liquid composition may be an aqueous composition.
  • the primary or even the only liquid diluting agent of a liquid aqueous composition is water.
  • the liquid aqueous composition may comprise certain amounts of organic diluents.
  • the organic diluents are the same or different from the at least one liquid carrier. It is preferred that a liquid aqueous composition comprises less than 35% by weight, preferably less than 25% by weight, more preferably less than 20% by weight and most preferably less than 10% or even less than 5% by weight of organic diluents, calculated on the total weight of the liquid composition. In a special embodiment, the liquid aqueous composition does not contain organic diluents at all.
  • a liquid aqueous composition comprises at least 10%, preferably at least 15%, more preferably at least 20% by weight of water. In certain cases, a liquid aqueous composition can comprise at least 25%, more preferably at least 30% by weight of water. In general, a liquid aqueous composition comprises at most 90% by weight of water, such as up to 80% or up to 70% by weight. In special embodiments, the liquid aqueous composition comprises up to 95%, or even up to 97, 98, or 99% by weight of water. In another embodiment, the liquid composition may be a non-aqueous composition. A non- aqueous liquid composition is essentially free from water.
  • a liquid composition suitably comprising water in an amount in the range of 0.0 to 10.0 % by weight, preferably in the range of 0.0 to 7.0 % by weight of water, calculated on the total weight of the liquid composition. More preferably, the non-aqueous liquid composition comprises less than 5.0 % by weight of water. For example, the liquid composition comprises less than 3.0 % by weight or less than 1.0% by weight of water, calculated on the total weight of the liquid composition.
  • the liquid composition is selected from a coating composition, a clear coat composition, a lacquer, a varnish, a plastic formulation, a pigment paste, an effect pigment paste, a polymer formulation, a sealant formulation, a cosmetic formulation, a homecare or industrial care formulation (including perfume and fragrance formulations), a ceramic formulation, an adhesive formulation, a liquid formulation for use in gas and oil production, a composition for the manufacture of electrical components and circuits, a liquid formulation for use in energy storage media, a cleaning agent, a potting compound, a building material formulation, a lubricant, a filling compound, a wax emulsion, a metalworking fluid, a metal- processing product, a liquid composition in the form of a spraying agent, a so-called deposition aid (e.g., for use in plant protection agents or for the general purpose of drift reduction), a ink, a printing ink and a ink jet ink or a composition that may be used as corrosion protection in the field of marine and protective coating
  • compositions wherein the composition according to the present invention can be used are solvent-based or solvent-free paints, printing inks and inks and lacquers as e. g., lacquers for varnishing of plastics, wire enamels, floor coatings, coating compositions for coating foodstuffs and seeds, and as so-called color resists, which are used for color filters, for example in flat panel displays such as liquid-crystal displays.
  • solvent-based or solvent-free paints e. g., lacquers for varnishing of plastics, wire enamels, floor coatings, coating compositions for coating foodstuffs and seeds, and as so-called color resists, which are used for color filters, for example in flat panel displays such as liquid-crystal displays.
  • the field of application lacquers also includes pasty materials which generally have a very high proportion of solids and a small proportion of liquid components, for example so-called pigment pastes or also pastes based on effect pigments, for example metal effect pigments such as, for example, aluminum pigments, silver pigments, brass pigments, zinc pigments, copper pigments, bronze pigments such as gold bronzes, fire-dyed bronzes or iron oxide aluminum pigments.
  • effect pigments also include, for example, interference pigments or pearlescent pigments such as, for example, metal oxide mica pigments, fish silver, bismuth oxide chloride or basic lead carbonate.
  • the plastic formulations can be liquid or non-liquid starting materials to produce plastic materials, which are preferably converted into a duromer by a chemical cross-linking process ("curing").
  • Preferred plastic preparations are unsaturated polyester resins, vinyl ester resins, acrylate resins, epoxy resins, polyurethane resins, formaldehyde resins (such as melamine- formaldehyde or urea-formaldehyde). These can be cured under very different conditions, e.g. at room temperature (cold-curing systems) or at elevated temperature (hot-curing systems), optionally with application of pressure ("closed mold” application, sheet molding compound or bulk molding compound).
  • the plastic formulations also include PVC plastisols.
  • the cosmetic preparations can be various liquid compositions, which are used in the so- called personal care or healthcare sector, e.g., lotions, creams, pastes such as, for example, toothpaste, foams such as, for example, shaving foam, gels such as, for example, shaving gels, shower gels or active ingredients in gel formulations, hair shampoos, liquid soaps, nail varnishes, lipsticks and hair dyes.
  • the so-called wax emulsions are preferably dispersions of solid waxes in particulate form at room temperature in water or an organic medium.
  • the building material formulations may be liquid or paste-like materials, which are used in the construction sector and solidify after curing. Examples are hydraulic binders such as concrete, cement, mortar, tile glue and plaster.
  • the metal working fluids may be cutting liquids, drilling fluids (such as are used in metal processing), or forging fluids or lubricants in general.
  • Potential other areas are release agents (often in the form of aqueous emulsions, for example, aluminum die casting and foundry applications), foundry washes (foundry coatings) and liquids for the surface treatment of metals (for example "surface finishing", surface treatment and plating).
  • the lubricants are means, which are used for lubrication, that is to say, which serve to reduce friction and wear, as well as to provide power, cooling, vibration dampening, sealing action and corrosion protection; liquid lubricants being preferred here.
  • Cleaning agents can be used to clean a wide range of objects, for example in the area of homecare or industrial care.
  • the cleaners also include detergents (primarily for cleaning textiles, their precursors, leather, and dish), and personal care products.
  • Formulations containing perfumes and other fragrances (either as liquid raw materials or in encapsulated form), e.g., as perfume gels, also belong to this area of application.
  • Liquid formulations used for gas and oil production are formulations used to develop and exploit a deposit. Drilling fluids or “drilling muds” are preferred examples.
  • Another application example are liquids used to prepare or perform a hydraulic fracturing process and liquids that support the production process of gas and oil.
  • the adhesives can be all adhesive materials which are liquid under processing conditions, and which can join parts by surface adhesion and internal strength.
  • the liquid compositions of the invention may further comprise customary additives.
  • additives are antiblocking 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 auxiliaries, and flame retardants.
  • Preferred additives are wetting agents, dispersants and/or emulsifiers and rheology additive which are different from the composition of the present invention, such as clay-based thickeners (including organoclays), (poly)amides, polysaccharides (like cellulose derivatives, guar, xanthan), polyacrylates, or associative thickeners.
  • inventive composition can be used in combination with other thickeners affecting the low, medium, and/or high shear performance of the liquid composition that needs to be modified concerning its rheological behavior.
  • the invention also relates to a process for controlling the rheology of a liquid composition
  • a process for controlling the rheology of a liquid composition comprising the steps of providing the 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 liquid compositions as aforementioned amongst others.
  • the step of mixing the components may be executed according to current processes known by the person skilled in the art. This may involve mixing by manual or electrical means inter alia. Mixing is combining the compositions and exerting shear force on the combined compositions.
  • the invention further deals with a liquid composition comprising the composition according to the invention and a binder.
  • binders comprise at least one of alkyd resins (such as short, medium, or long oil alkyd), unsaturated polyester resins, vinylester resins, acrylate resins, epoxy resins, polyurethane resins, polyaspartic resins, phenolic binders, silicones, chlorinated rubbers, vinyl based binders, poly(vinyl alcohol), poly(vinyl acetates), saturated polyester binders, polyacrylates and acrylate copolymers, urea and melamine resins, silicate binders, cellulose based binders, and silyl modified polymers.
  • alkyd resins such as short, medium, or long oil alkyd
  • unsaturated polyester resins such as short, medium, or long oil alkyd
  • vinylester resins such as short, medium, or long oil alkyd
  • acrylate resins epoxy resins, polyurethane resins, polyaspartic resins, phenolic binders, silicones, chlorinated rubbers
  • Preferred binders comprise at least one of alkyd resins (such as short, medium, or long oil alkyd), unsaturated polyester resins, vinylester resins, acrylate resins, epoxy resins, polyurethane resins, polyacrylates and acrylate copolymers, polyaspartic resins, and silyl modified polymers.
  • alkyd resins such as short, medium, or long oil alkyd
  • vinylester resins vinylester resins
  • acrylate resins epoxy resins
  • polyurethane resins polyacrylates and acrylate copolymers
  • polyaspartic resins polyaspartic resins
  • silyl modified polymers silyl modified polymers.
  • These binders can preferably be solvent-borne, solvent-free, or aqueous binders.
  • Solvent- borne and aqueous binders can be delivered both as solutions, emulsions, or dispersions.
  • the above-mentioned binders also comprise aqueous binder systems like styrene- acrylic dispersions, urethane-acrylic dispersions, and alkyd emulsions.
  • the binders also comprise non-aqueous dispersion (NAD) systems.
  • Another object of the invention is an article, wherein at least a part of the surface of the article is coated with the liquid composition.
  • the coated article is obtainable by the steps of providing an article, providing the liquid composition according to the present invention and coating at least a part of the surface of the article with the liquid composition.
  • the 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 wherein the liquid composition is hardened.
  • the coated article is obtainable by the steps of providing an article, providing the liquid composition according to the present invention, coating at least a part of the surface of the article with the liquid composition and hardening the liquid composition.
  • Suitable articles are all three-dimensional objects, irrespective of their size and volume and whether they are mobile or immobile.
  • Illustrative, but not limiting examples are building interiors and exteriors, flooring, furniture, vehicles used for transportation (like automobiles, bikes, boats, aircrafts, agricultural machines, and all kinds of freight vehicles), bridges and tunnels, machinery and production equipment, electrical devices, cans, metal coils, wires, containers, household articles and hardware, pulp and paper, as well as all kind of articles made of wood, metal, plastics or glass (e.g., for functional or ornamental use).
  • the meaning of the wording “coating” is well-known to the person skilled in the art. In this context, it relates to the application of the liquid composition on the surface or other areas of said article to cover it at least partly or even encasing the article in its entirety.
  • the liquid composition toughens or hardens after it has been applied to said article.
  • Hardening means converting the liquid composition into a solid state. This can be achieved by evaporation of liquid diluents (physical drying) or by chemical crosslinking reaction (curing), and by combinations thereof.
  • the invention is illustrated further below giving reference to examples.
  • the choice of the respective reaction conditions, as e. g., the reaction temperature, reaction time and dosing rates are known to the skilled person and are illustrated in more detail in the working examples.
  • Comparative Rheology Additive C8 In a four-neck flask with stirrer, 1.22 g of lithium chloride were added to 78.8 g of DMSO under stirring. The mixture was heated up to 80 °C under nitrogen atmosphere. The lithium chloride was dissolved within 30 min under stirring.1.68 g (28.0 mmol) ethane-1,2-diamine were added, and the mixture was homogenized.18.3 g of the intermediate I4 were added dropwise under stirring within 30 min in such a way that the temperature did not exceed 85 °C. Afterwards the mixture was stirred for 3 hours at 80°C.
  • Rheology Additive according to the Invention E29 In a four-neck flask with stirrer, 6.00 g of 1,3-dimethylurea were added to 74 g of DMSO under stirring. The mixture was heated up to 80°C under nitrogen atmosphere. The 1,3- dimethylurea was dissolved within 30 min under stirring.1.68 g (28.0 mmol) ethane-1,2- diamine were added, and the mixture was homogenized.18.3 g of the intermediate I4 were added dropwise under stirring within 30 min in such a way that the temperature did not exceed 85 °C. Afterwards the mixture was stirred for 3 hours at 80°C. The result is a transparent, yellowish product.
  • the inventive examples comprise a liquid carrier and a stabilizing agent (urea compound having a molecular weight below 350 g/mol) whereas the corresponding non-inventive examples only contain the liquid carrier.
  • the inventive example and corresponding non-inventive example contain the same amount of the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group. **) Time between synthesis and formation of precipitate or gelation. From table 5a it is visible that the inventive examples E 1- 26, E 29 and E 32- 38 show a significantly increased storage stability compared to their corresponding non-inventive examples.
  • the Hazen color numbers and Gardner color numbers of examples C9, E30 and E31 were determined using a spectral photometer LCS IV (BYK-Gardner GmbH).
  • the Hazen scale is a color standard used to assess the intensities of transparent, light yellow-tinted samples compared to a color reference standard solution according to DIN EN ISO 6271 reaching from 0 (no color) to 500 (light yellow).
  • the Gardner scale is a color standard used to assess the intensities of transparent, more strongly colored samples compared to color reference standard solutions according to DIN EN ISO 6271 reaching from 1 (light yellow) to 18 (dark brown).
  • component A All ingredients of component A were added under stirring conditions into a PE beaker and homogenized with a Dispermat LC3 (VMA Getzmann), 1000 rpm, 4 cm diameter toothed plate, 10 minutes at room temperature (23 °C). Afterwards the pH of component A was adjusted with DMEA solution (10% in water) to pH 8.2-8.5. Component B was produced with the same stirring conditions.
  • Component A was divided into smaller amounts (50 g in 175 ml PE beaker) and the inventive and non-inventive compositions were incorporated with a dosage of 0.5 weight-% of the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group (calculated on the total clearcoat) under stirring with Dispermat LC3 (VMA Getzmann), 1500 rpm, 2.5 cm diameter toothed plate, 5 minutes at room temperature (23 °C). After storage at room temperature over night the hardener solution was added with the specified mixing ratio and homogenized by stirring with spatula.
  • VMA Getzmann VMA Getzmann
  • Component A was divided in smaller amounts (50 g in 100 ml glass bottle) and the inventive and non-inventive compositions were incorporated with a dosage of 0.5 weight-% of the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group (calculated on the total clearcoat) under stirring with Dispermat LC3 (VMA Getzmann), 1500 rpm, 2.5 cm diameter toothed plate, 5 minutes at room temperature (23 °C). After storage at room temperature over night the hardener was added with the specified mixing ratio and homogenized by stirring with spatula.
  • VMA Getzmann VMA Getzmann
  • Table 9 Solvent based 2-pack PU Clearcoat Component A: Setalux DA 870 80.0 g BA n-Butyl acetate 9.9 g Dowanol PMA 9.9 g BYK-066 N 0.2 g 100.0 g Dispermat: 5 min. at 1000 rpm with 4 cm diameter toothed plate Component B: Desmodur N3390BA 50.0 g Ratio Comp. A : Comp.
  • Test 3 Sag resistance in a thermoplastic acrylic clearcoat Production of the thermoplastic acrylic clearcoat was carried out using the formulation in table 11. All ingredients were added under stirring conditions into a PE beaker and homogenized with a Dispermat LC3 (VMA Getzmann), 1000 rpm, 4 cm diameter toothed plate, 15 minutes at room temperature (23 °C).
  • the clearcoat was divided in smaller amounts (50 g in 100 ml glass bottle) and the inventive and non-inventive compositions were incorporated with a dosage of 0.75 weight-% (column I in table 12) and 1.0 weight-% (column II in table 12) of the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group (calculated on the total clearcoat) under stirring with Dispermat LC3 (VMA Getzmann), 1500 rpm, 2.5 cm diameter toothed plate, 5 minutes at room temperature (23°C).
  • VMA Getzmann Dispermat LC3
  • Table 11 Solvent based thermoplastic acrylic clearcoat Paraloid B66 25.0 g Oxsol 100 48.7 g Tert.-Butyl acetate 11.3 g Acetone 15.0 g 100.0 g Dispermat: 15 min. at 1000 rpm with 4 cm diameter toothed plate
  • Table 12 Results Example Sag resistance [ ⁇ m] I II (0.75 wt.%) (1.0 wt.%) Control (without ⁇ 50 ⁇ 50 rheology additive) C2 150 150 E2 500 750 E4 500 800 E6 550 750 E9 400 800 E11 450 750 From table 12 it was surprisingly found that the inventive rheology additives E2, E4, E6, E9, and E11 show a better sag resistance in the thermoplastic acrylic clearcoat than the comparative rheology additive C2.
  • Test 4 Rheology effect and compatibility in various solvents Various solvents were filled with an amount of 50 g in 100 ml glass bottles.
  • the inventive and non-inventive compositions were incorporated with a dosage of 1.0 weight% of the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group (calculated on the amount of the solvent) under stirring with Dispermat LC3 (VMA Getzmann), 1500 rpm, 2.5 cm diameter toothed plate, 5 minutes at room temperature (23 °C). After storage over night at room temperature, the samples were evaluated regarding gel strength (rheology effect) and turbidity (compatibility).
  • the visual evaluation of the gel strength can vary from a strong gel (gel strength rating “1”) to no gel (gel strength rating “5”) and the turbidity from clear (turbidity rating “1”) to strong turbidity (turbidity rating “5”).
  • Table 13 Tested solvents Acetone Methylamylketone (MAK) Xylene
  • Table 14a Results Example Gel strength Acetone MAK Xylene Control (without 5 5 5 rheology additive) C2 5 5 5 5 E2 1 1 1 1 E4 1 1 1 1 E6 1 1 1 1 E9 1 1 1 E11 1 1 1 1 From table 14a it was surprisingly found that the inventive rheology additives E2, E4, E6, E9, and E11 show a better gel strength, in the respective solvents than the comparative rheology additive C2.
  • Table 14b Results Example Turbidity MAK Xylene Control (without rheology 1 1 additive) C2 5 5 E2 1 2 E4 1 1 E6 1 1 E9 2 4 E11 1 1 From table 14b it was surprisingly found that the inventive rheology additives E2, E4, E6, E9, and E11 show less influence on turbidity in the respective solvents than the comparative rheology additive C2.
  • Test 5 Sag resistance in a long oil alkyd clearcoat Production of the solventbased long oil alkyd clearcoat was carried out using the formulation in table 15.
  • Table 16 Results Example Sag resistance [ ⁇ m] Gloss 20° Control without ⁇ 30 87 rheology additive C6 150 51 E27 270 70 E28 300 76 From table 16 it was surprisingly found that the inventive rheology additives E27 and E28 show a better sag resistance and higher gloss in the long oil alkyd clearcoat than the comparative rheology additive C6.
  • Test 6 Whitening of a solventbased long oil alkyd clearcoat Production of the solventbased long oil alkyd clearcoat was carried out using the formulation in table 17.
  • Table 17 Solvent based long oil alkyd clearcoat Worléekyd S365, 60% in white spirit 80.9 g White spirit 13.7 g Nuodex Combi APB 4.9 g Borchinox M 2 0.3 g BYK-066 N 0.2 g 100.0 g Dispermat: 10 min. at 1000 rpm with 4 cm diameter toothed plate
  • Table 18 Results Example Visual evaluation of Whitening viscosity Control without low 2 rheology additive C6 high 5 E27 high 3 E28 high 3-4 While the control without rheology additive exhibits a low viscosity, the samples with the rheology additives C6, E27 and E28 show a significantly higher viscosity.
  • Component A was divided in smaller amounts (50 g in 100 ml glass bottle) and the inventive compositions were incorporated with a dosage of 1.0 weight-% of the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group (calculated on the total lacquer) under stirring with Dispermat LC3 (VMA Getzmann), 1500 rpm, 2.5 cm diameter toothed plate, 5 minutes at room temperature (23 °C). After storage at room temperature over night the hardener was added with the specified mixing ratio and homogenized by stirring with spatula.
  • the samples were applied with a wire bar (BYK Gardner GmbH) with 200 ⁇ m wet film thickness on DIN A4 white primered aluminium panels (Novelis GmbH) and dried at room temperature for 1 day.
  • the degree of yellowing was determined using the color spectrophotometer Color Guide 45/0 (BYK-Gardner GmbH) one day after application.
  • the YE 98 values were measured and compared. DYE 98 was calculated as the difference of the degree of yellowing of the sample without rheology additive (control) to the respective samples with rheology additive.
  • Table 19 Solvent based 2-pack PU Clearcoat Component A: Setalux DA 870 80.0 g BA n-Butyl acetate 9.9 g Dowanol PMA 9.9 g BYK-066 N 0.2 g 100.0 g Dispermat: 5 min. at 1000 rpm with 4 cm diameter toothed plate Component B: Desmodur N3390 BA 50.0 g Ratio Comp. A : Comp.
  • component A All ingredients of component A were added under stirring conditions into a PE beaker and homogenized with a Dispermat LC3 (VMA Getzmann), 1000 rpm, 4 cm diameter toothed plate, 5 minutes at room temperature (23 °C).
  • the inventive compositions were incorporated with a dosage of 0.55 weight-% of the component having a number average molecular weight Mn in the range of 400 g/mol to 30000 g/mol and having at least one urea group (calculated on the total lacquer) under stirring with Dispermat LC3 (VMA Getzmann), 1500 rpm, 2.5 cm diameter toothed plate, 5 minutes at room temperature (23 °C).
  • the gel strength and turbidity were evaluated visually with a scale of 1 – 5 for gel strength (no gel formation – strong gel formation) and turbidity (clear – strong turbidity).
  • the hardener was added with the specified mixing ratio and homogenized by stirring with spatula until the clear coat composition was optically homogeneous.
  • the efflux time of the clear coat composition was then determined using a DIN 4 mm flow cup (BYK-Gardner GmbH).
  • the clear coat composition was diluted with a solvent mixture (n-butylacetate / Dowanol PMA; 40:60 w/w) to adjust a DIN 4 efflux time of 21 s (+/- 1 s) for the application.
  • the application of the clear coat composition was carried out by means of pneumatic spray application Eisenmann LaTec GmbH (spray gun AGMD Pro (De Vilbiss), 1.2 mm nozzle De Vilbiss GTI PRO High Efficiency TE 40 C; air flow speed: 0.6 m/s) on vertically suspended, primed and perforated steel plates (N / 16300500L cold rolled fine sheet incl 16 holes a 10 mm with protective coating (gray/white, application side gray 300 mm x 500 mm x 0.60 - 0.70 mm).
  • the clear coat was applied in three spray passes to determine the sag limit of the clear coat composition.
  • the coated sheets were vented vertically at room temperature for 10 minutes and then dried vertically at 60 °C for 60 minutes in a VTL 60/90 reflow oven (from Votsch Industrietechnik GmbH). After 24 h the determination of the sag limit was made by optically determining that spot on the perforated plate, that had no clear coat accumulation under the hole (no distinct bulg or runner formation). The determination of the dry layer thickness above and below the determined hole with the dry-film measuring device Byko-Test 1500 (BYK-Gardner GmbH) was carried out by a 3-time measurement and the subsequent averaging.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne une composition comprenant un support liquide qui est liquide à une température de 20°C, un composant ayant un poids moléculaire moyen en nombre Mn dans la plage de 400 g/mol à 30000 g/mol et ayant au moins un groupe urée, dissous dans le support liquide, et un composé d'urée ayant un poids moléculaire inférieur à 350 g/mol dissous dans le support liquide.
EP23837223.9A 2022-12-21 2023-12-20 Agent de régulation de rhéologie liquide Pending EP4638538A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP22215266 2022-12-21
PCT/EP2023/086909 WO2024133435A1 (fr) 2022-12-21 2023-12-20 Agent de régulation de rhéologie liquide

Publications (1)

Publication Number Publication Date
EP4638538A1 true EP4638538A1 (fr) 2025-10-29

Family

ID=84901271

Family Applications (1)

Application Number Title Priority Date Filing Date
EP23837223.9A Pending EP4638538A1 (fr) 2022-12-21 2023-12-20 Agent de régulation de rhéologie liquide

Country Status (5)

Country Link
EP (1) EP4638538A1 (fr)
JP (1) JP2026502150A (fr)
KR (1) KR20250112841A (fr)
CN (1) CN120303314A (fr)
WO (1) WO2024133435A1 (fr)

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10039837C2 (de) 2000-08-16 2003-03-20 Byk Chemie Gmbh Verfahren zur Herstellung einer lagerstabilen, rheologisch wirksamen Harnstoffurethan-Lösung mit breiter Verträglichkeit
DE10241853B3 (de) 2002-09-09 2004-01-22 Byk-Chemie Gmbh Polymeres Harnstoffurethan als Rheologiesteuerungsmittel und Verfahren zur Herstellung
ES2358486T3 (es) * 2005-06-28 2011-05-11 Nuplex Resins B.V. Producto de poliurea como agente modificador de la reología tixotrópico.
EP2110397A1 (fr) * 2008-04-16 2009-10-21 Sika Technology AG Polymère de polyuréthane basé sur des blocs de copolymères amphiphiles et leur utilisation comme modificateur de résistance aux chocs
DE102008059702A1 (de) 2008-12-01 2010-06-02 Byk-Chemie Gmbh Verfahren zur Herstellung rheologisch wirksamer Harnstoffurethane in organischen Salzen
PL3131962T3 (pl) 2014-04-15 2018-09-28 Byk-Chemie Gmbh Kompozycja do regulowania właściwości reologicznych

Also Published As

Publication number Publication date
JP2026502150A (ja) 2026-01-21
WO2024133435A1 (fr) 2024-06-27
CN120303314A (zh) 2025-07-11
KR20250112841A (ko) 2025-07-24

Similar Documents

Publication Publication Date Title
CN113840858B (zh) 含有环酰胺的流变控制添加剂
US10407385B2 (en) Ureaurethanes for rheology control
US9796860B2 (en) Storage-stable urea preparations which are suitable as rheology control agents
KR102148891B1 (ko) 유동성 조절용 조성물
US11453750B2 (en) Urea-group- and/or urethane-group-containing amides as and in rheology control agents, their preparation and their use
EP4638538A1 (fr) Agent de régulation de rhéologie liquide
EP4551655B1 (fr) Composition comprenant un amide cyclique
KR102657317B1 (ko) 우레아 기 함유 레올로지 제어 첨가제
WO2025068507A1 (fr) Agent de régulation de rhéologie
WO2026027417A1 (fr) Agent de contrôle de rhéologie
KR20260053559A (ko) 레올로지 조절제
WO2022117621A1 (fr) Agent de régulation de la rhéologie

Legal Events

Date Code Title Description
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: UNKNOWN

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE

PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

17P Request for examination filed

Effective date: 20250721

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC ME MK MT NL NO PL PT RO RS SE SI SK SM TR

DAV Request for validation of the european patent (deleted)
DAX Request for extension of the european patent (deleted)