WO2011070074A1 - Produits d'addition époxyde-amine modifiés par polyéther comme agents mouillants et dispersants - Google Patents

Produits d'addition époxyde-amine modifiés par polyéther comme agents mouillants et dispersants Download PDF

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Publication number
WO2011070074A1
WO2011070074A1 PCT/EP2010/069182 EP2010069182W WO2011070074A1 WO 2011070074 A1 WO2011070074 A1 WO 2011070074A1 EP 2010069182 W EP2010069182 W EP 2010069182W WO 2011070074 A1 WO2011070074 A1 WO 2011070074A1
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Prior art keywords
addition compound
aryl
alkyl
compound according
general formula
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PCT/EP2010/069182
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German (de)
English (en)
Inventor
Ulrich Orth
Heribert Holtkamp
Jürgen OMEIS
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Byk-Chemie Gmbh
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Publication date
Application filed by Byk-Chemie Gmbh filed Critical Byk-Chemie Gmbh
Priority to CN201080056078.5A priority Critical patent/CN102652146B/zh
Priority to JP2012542539A priority patent/JP5685266B2/ja
Priority to KR1020127015100A priority patent/KR101801835B1/ko
Priority to EP10787471.1A priority patent/EP2510034B1/fr
Priority to US13/511,587 priority patent/US9340641B2/en
Publication of WO2011070074A1 publication Critical patent/WO2011070074A1/fr

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    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/182—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents
    • C08G59/184—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents with amines
    • 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
    • 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
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
    • C08G18/6415—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63 having nitrogen
    • C08G18/643—Reaction products of epoxy resins with at least equivalent amounts of amines
    • 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
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • 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
    • 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
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4014—Nitrogen containing compounds
    • C08G59/4028—Isocyanates; Thioisocyanates
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C08G59/504—Amines containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C08L75/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives

Definitions

  • the invention relates to reaction products of epoxides with amines, polyether-modified amines and polyalkylene oxide-modified and / or polyester-modified and / or polyether-polyester-modified isocyanates to amine, comb-like polymers and their salts as wetting agents and dispersants for pigments and fillers and to a process for their production.
  • the invention further relates to the use of these reaction products as wetting and dispersing agents for organic and inorganic pigments, as well as fillers in aqueous, solvent-based and radiation-curable systems.
  • reaction products are particularly suitable for the production of pigment concentrates and for stabilizing solids in binders, paints, plastics and plastic mixtures.
  • wetting and dispersing agents they reduce the viscosity of such systems, improve storage stability and flow properties and can increase color strength.
  • a known group of such dispersants is based on reaction products of mono- or polyepoxides with amines containing an imidazoline moiety. An overview of this group of dispersants can be found inter alia in US Pat. Nos. 5,128,393 and 4,710,561. Another group of dispersants is formed from polyepoxide / amine mixtures and their salts. From the publications DE 36 23 296 A and DE 36 23 297 A, the use of such mixtures as a dispersant for pigments is known primarily in organic media, wherein the polyepoxides are novolacs and as amines aliphatic, aromatic and / or heterocyclic amines low molecular weight can be used.
  • dispersants have in common that they have each been developed for a narrowly limited field of use and are therefore geared specifically to the pigment-binder mixture. In systems with very different polarity, however, they are only of limited use.
  • modular components are preferably used in the course of streamlined processes. These modular components should be well compatible with the other components such as binders, excipients and solvents within the meaning of a modular system.
  • the wetting and dispersing agents are said to reduce the viscosity without adversely affecting the gloss and haze of a finish containing the wetting and dispersing agent.
  • a method for producing such wetting and dispersing agents should be specified.
  • R C 1 -C 24 -alkyl, C 5 -C 12 -cycloalkyl, C 6 -C 10 -aryl, C 6 -C 18 -aralkyl, R 1 and R 2 may be, independently of one another, identical or different and H, C 1 -C 24 -alkyl, Aryl, and / or -CH 2 -OC n H 2n + 1 , x can be arranged blockwise or randomly and is preferably 10 to 100, preferably 20 to 70, particularly preferably 35 to 50,
  • R 6 is alkyl, cycloalkyl, aryl and aralkyl and Z is another functional group selected from -OH, tertiary amine or a heterocyclic radical having a 5 or 6-membered ring, the as heteroatoms preferably contains N and / or O, such as N- (3-Arninopropyl) -imidazole or N- (2-aminoethyl) -morpholin, may be,
  • R 3 alkyl, cycloalkyl, aryl and / or aralkyl
  • R 4 and R 5 are independently H, alkyl and / or aryl
  • X alkylene, cycloalkylene and / or aralkylene
  • Y alkylene and / or cycloalkylene
  • n and m are independently 0 to 100, preferably 1 to 100, more preferably 2 to 100, wherein the sum is n + m ⁇ 2, to form a urethane.
  • the urethanes formed preferably have a calculated number average molecular weight of 1,800 to 100,000 g / mol. Particularly preferred are urethanes with a calculated number average molecular weight of 2000 to 70000 g / mol, very particularly preferably 10000 to 60000 g / mol.
  • the addition compounds according to the invention have a broad availability.
  • the urethane bond additionally present in the compounds according to the invention allows both a broad compatibility with common binder solvent systems and an advantageous long-term and storage stability due to their chemical inertness. It is particularly surprising that the wetting and dispersing agents can reduce the viscosity without adversely affecting the gloss and haze of a finish containing the wetting and dispersing agent.
  • aromatic-containing and / or aliphatic polyepoxides can be used.
  • the polyepoxides may contain two or more epoxide groups per molecule and have at least six carbon atoms. It is also possible to use mixtures of different polyepoxides.
  • Typical examples from the group of aromatic polyepoxides are reaction products of diphenylolpropane (bisphenol A) with epichlorohydrin and their higher homologs, which are available, for example, under the brand names DER or Epikote from the DOW Chemical Company or from Resolution Performance Products.
  • aliphatic polyepoxides are, for example, 1,6-hexanediglycidyl ether and 1,4-butanediglycidyl ether.
  • the aliphatic polyepoxides may also contain additional oxygen in the chain, such as.
  • These aliphatic polyepoxides Ems-Chemie eg under the trade name Grilonit ® from. Available.
  • polyether component B is preferably methanol Started polyethylene glycol-polypropylene glycols having terminal primary amino group, which are based on ethylene oxide and propylene oxide, and under the trade designation Jeffamine ® from. Huntsman are commercially available.
  • polyetheramines are also used whose polyether part is based on other epoxides, for example butylene oxide, 1,2-epoxyhexane, 2-ethylhexyl glycidyl ether or styrene oxide.
  • the distribution of the epoxide units when using different epoxides blockwise or statistically.
  • the aliphatic and / or aliphatic amines of component C preferably have 3 to 28 carbon atoms. Examples of these are aminohexane, stearylamine, oleylamine and benzylamine or cyclohexylamine. As additional functional groups, hydroxyl groups or tertiary amino groups are particularly preferred. Examples of amines with functional groups are e.g. Ethanolamine, butanolamine, 2-amino-2-methyl-1-propanol, or amines having more than one additional functional group, e.g. 2-amino-2-ethyl-1,3-propanediol or 2-amino-2-hydroxymethyl-1,3-propanediol.
  • amines having heterocyclic radicals are N- (3-aminopropyl) imidazole or N- (2-aminoethyl) morpholine.
  • components A and (B + C) can be reacted with each other in a stoichiometric excess of component A to form epoxide-terminated polymers.
  • the components A and (B + C) can be reacted with each other in a stoichiometric excess of the components (B + C) to form amine-terminated polymers.
  • component A is added to the sum of components B and C in a molar ratio of 33:32 to 32:33.
  • the components A, B and C are preferably used in a molar ratio in which A, B and C are completely reacted.
  • the molar ratio of component B to component C is preferably from 2:30 to 30: 2.
  • component D is used in an amount of 5-100%, preferably 20-100% and more preferably 40-100% of the OH groups generated by the addition of the components A and (B +) are reacted with urethane formation.
  • component A particular preference is given to using aliphatic diepoxide compounds having an average of two epoxy functions per molecule and more preferably diglycidyl ethers of diols.
  • the addition compounds obtained from components A, B, C and D are high quality and broadly compatible wetting and dispersing agents. They can be used in the form in which they are obtained by the two-stage reaction. However, in some cases, to tailor their properties to specific requirements, it is desirable to further modify them. Described below are suitable modifications based on reaction with the hydroxyl and / or amino groups present in the addition compounds. These can be fully or partially implemented during the modification.
  • modification reactions may be combined as needed to give polymodified addition compounds. If several modification reactions are carried out consecutively, care must be taken to obtain enough reactive groups for one or more subsequent reactions in the molecule.
  • the modifications mentioned are advantageous embodiments of the present invention and can be realized by: 1. reaction of the terminal amino groups with isocyanates, lactones, cyclic carbonates or (meth) acrylates,
  • (meth) aryl is meant both acrylic and methacrylic compounds.
  • (meth) acrylate means both acrylate and methacrylate compounds.
  • the free epoxide groups which may remain in the addition compounds according to the invention can be esterified with carboxylic acids as indicated under 2.).
  • carboxylic acids as indicated under 2.
  • the esterification with (meth) acrylic acid to obtain the double bond for radiation curing.
  • the free hydroxyl groups which may remain in the addition compounds according to the invention may be esterified as stated under 3., 4. and 5.).
  • the esterification takes place in a manner known to those skilled in the art. If additional free amino groups are present in the addition product according to the invention, it is advisable to salify them before the esterification in order to obtain a satisfactory Reaction speed to achieve. In this transesterification terminal OH groups are retained, whereby the resulting products are characterized by a particularly broad compatibility in many coating systems.
  • the compounds formed in the inventive addition with any remaining hydroxyl groups can furthermore be reacted according to 6.) with isocyanates.
  • the urethane formation is carried out in a manner known to the person skilled in the art.
  • the conversion of the hydroxyl group into a urethane group is preferably carried out when hydroxyl groups in the paint system interfere.
  • the further formation of urethane can have a favorable effect on the defoaming action of the wetting and dispersing agents.
  • the suppression of foaming tendency is an important additional property of the wetting and dispersing agents, especially in antebusts in aqueous formulations.
  • reaction of the epoxide function of component A with the amino groups of components B and C to form the .beta.-hydroxyamino function can be carried out in a solvent system, but preferably in substance according to the methods known to the person skilled in the art.
  • the reaction temperature to be selected depends on the reactivity of the educts. Many epoxides react with amines even at room temperature. By contrast, reaction temperatures of up to 160 ° C. may be necessary for less reactive epoxides. Particularly suitable reaction temperatures for the reaction of epoxides with amines are at 50-120 ° C.
  • catalysts known to those skilled in the art can be used to promote the reaction of the epoxide with the amine.
  • Component D is preferably prepared by the processes described in DE 199 19 482 A1. These are monohydroxy compounds with a Excess diisocyanate, preferably tolylene diisocyanate, reacted and the unreacted portion of the diisocyanate is removed from the reaction mixture.
  • a Excess diisocyanate preferably tolylene diisocyanate
  • the object of the present invention is likewise achieved by a process for preparing a suitable as wetting and dispersing addition compound by reacting
  • R C 1 -C 24 -alkyl, C 5 -C 12 -cycloalkyl, Ce-C 1 o-Aryi, Ce-C - ⁇ -aralkyl, R 1 and R 2 can be identical or different and H, C 1 -C 24 -alkyl, aryl, and / or -CH 2 -OC n H 2n + 1 , x may be arranged blockwise or randomly and preferably 10 to 100, preferably 20 to 70, particularly preferably 35 to 50 is
  • R ö alkyl, cycloalkyl, aryl and aralkyl and Z is another functional group selected from -OH, tertiary amine or a heterocyclic radical having a 5 or 6-membered ring, which are heteroatoms preferably N and / or O, such as N- (3-aminopropyl) -imidazole or N- (2-aminoethyl) -morpholine, may be, D) at least one modified isocyanate of the general formula (IIIa) and / or (Mb)
  • R 3 is alkyl, cycloalkyl, aryl and / or aralkyf
  • R 4 and R 5 independently of one another are H, alkyl and / or aryl
  • Y alkylene and / or cycloalkylene
  • n and m are independently 0 to 100, preferably 1 to 100, more preferably 2 to 100, wherein the sum is n + m> 2, to form a urethane.
  • component D the amount of this component used is preferably selected so that in the addition reaction 5-100%, preferably 20-100% and particularly preferably 40-100%, by the addition of the components A and (B + C) generated OH groups are reacted with urethane formation. In this way, a particularly good compatibility of the addition compound with binders is achieved, especially in aqueous systems.
  • the addition compounds of the invention are used as wetting and / or dispersing agents for organic and / or inorganic pigments or fillers.
  • the dispersants can be used alone or together with binders.
  • the wetting and dispersing agents according to the invention are particularly preferably used in aqueous and / or solvent-based paints for stabilizing and dispersing pigments and fillers.
  • the addition compounds according to the invention are used as wetting and / or dispersing agents for organic and / or inorganic pigments or fillers in radiation-curable systems.
  • a coating of the pigment surface can take place during or after the synthesis of the pigments, for example by adding the addition compounds according to the invention to the pigment suspension.
  • Pre-treated pigments in this way show easy incorporation into the binder system, improved viscosity and storage behavior, and good gloss over untreated pigments.
  • the addition compounds according to the invention are suitable for dispersing e.g. Effect pigments in nail polishes.
  • the dispersants of the invention are preferably used in an amount of 0.5-60 wt .-% based on the solid to be dispersed. With special solids, however, substantially higher amounts of dispersant may be necessary for dispersion.
  • the amount of dispersant used is essentially dependent on the size and type of surface of the solid to be dispersed. For example, carbon black requires much larger amounts of dispersant than titanium dioxide.
  • EP 0 270 126 A contains examples of pigments and fillers. Further examples are based on new developments, in particular in the field of organic pigments, such as in the class of diketo-pyrrolo-pyrroles.
  • M2000 methoxypolyethylene glycol (mol. Wt.
  • MP41-2000 methoxypolyethylene-polypropylene glycol (mol. Wt. 2000, E07PO4 / 1)
  • Grilonite F704 polypropylene glycol diglycidyl ether (about 7 PO)
  • B11 / 120 butoxypolyethyleneglycol-polypropylene glycol (mol.wt .: about 2000; EO / PO: 1: 1)
  • Jeffamine M2070 methoxypolyethyleneglycol-polypropyleneglycolamine, (mol. Wt .: ca. 2000; EO / PO: 32: 10)
  • Jeffamin M2005 methoxypolyethyleneglycol-polypropylengiykolamin, (mol.wt .: about 2000; EO / PO: 6:29)
  • binder-free pigment pastes were prepared, which were incorporated into a binder (Johncryl 8052). The viscosity was assessed. After application and curing of the finished pigment coatings, the elevators were then visually assessed and gloss and haze measurements made.
  • the dispersion of the components of the formulation takes place over 40-60 min. at 40 ° C. and 10,000 rpm with the aid of a Dispermate CV from VMA-Getzmann GmbH
  • Johncryl 8052 acrylate dispersion from Johnson Polymers
  • Irgalithrot FBN Naphtol-AS pigment from Ciba
  • Printex 35 black pigment (furnace carbon black) from Degussa
  • Sunfast blue 249-1282 phthalocyanine pigment from Sun-Chemicals
  • the pigment pastes are then added in a ratio of 30:70 to the binder Johncryl 8052. evaluation

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne un composé d'addition approprié comme agent mouillant et dispersant, pouvant être obtenu par la réaction A) de polyépoxydes avec B) au moins une polyoxyalkylèneamine primaire, C) au moins une autre amine primaire aliphatique et/ou araliphatique et D) au moins un isocyanate modifié.
PCT/EP2010/069182 2009-12-11 2010-12-08 Produits d'addition époxyde-amine modifiés par polyéther comme agents mouillants et dispersants WO2011070074A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CN201080056078.5A CN102652146B (zh) 2009-12-11 2010-12-08 作为润湿分散剂的聚醚改性的环氧胺加合物
JP2012542539A JP5685266B2 (ja) 2009-12-11 2010-12-08 湿潤剤および分散剤としてのポリエーテル変性エポキシアミン付加物
KR1020127015100A KR101801835B1 (ko) 2009-12-11 2010-12-08 습윤제 및 분산제로서의 폴리에테르 개질된 에폭시 아민 부가물
EP10787471.1A EP2510034B1 (fr) 2009-12-11 2010-12-08 Produit d'addition en époxyde-amine modifié par polyéthers en tant qu'agent mouillant et dispersant
US13/511,587 US9340641B2 (en) 2009-12-11 2010-12-08 Polyether-modified epoxy amine adducts as wetting and dispersing agents

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016059066A1 (fr) 2014-10-14 2016-04-21 Byk-Chemie Gmbh Produits d'addition époxy-amine pour la dispersion de matières solides
WO2018184961A1 (fr) 2017-04-05 2018-10-11 Byk-Chemie Gmbh Produits d'addition monoépoxyde-monoamine en tant qu'agents mouillants et dispersants
US11453748B2 (en) 2017-08-08 2022-09-27 Byk-Chemie Gmbh Amine functional compound

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016193473A1 (fr) 2015-06-03 2016-12-08 Byk-Chemie Gmbh Produits de réaction contenant des groupes uréthane
TWI548673B (zh) 2015-11-05 2016-09-11 財團法人工業技術研究院 聚合物與分散液
CA3060348A1 (fr) * 2017-06-28 2019-01-03 Huntsman Petrochemical Llc Polyetheramines amorcees par un alcool tetrahydrofurfurylique et leurs utilisations
JP7475270B2 (ja) 2017-07-20 2024-04-26 ソルヴェイ（ソシエテ アノニム） 発泡剤としての官能化微粒子重炭酸塩、それを含有する発泡性ポリマー組成物、及び熱可塑性発泡ポリマーの製造でのその使用
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EP3505550B1 (fr) * 2017-12-27 2022-06-22 Evonik Operations GmbH Agents mouillants et dispersants présentant des propriétés rhéologiques
CN112584922B (zh) * 2018-08-22 2023-01-24 路博润先进材料公司 芳香族酰胺分散剂
CN111154059B (zh) * 2020-01-16 2021-09-10 上海汇得科技股份有限公司 一种环氧树脂改性聚醚胺增强水性聚氨酯乳液及制备方法
EP4008738A1 (fr) 2020-12-02 2022-06-08 CliQ SwissTech (Netherlands) B.V. Copolymères séquencés à poids moléculaire élevé

Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4710561A (en) 1985-11-27 1987-12-01 Kansai Paint Co., Ltd. [Poly]imidazoline adduct for electrocoating
DE3623296A1 (de) 1986-07-11 1988-01-14 Hoechst Ag Additionsverbindungen, verfahren zu ihrer herstellung und ihre verwendung
DE3623297A1 (de) 1986-07-11 1988-01-21 Hoechst Ag Additionsverbindungen, verfahren zu ihrer herstellung und ihre verwendung
EP0270126A2 (fr) 1986-12-05 1988-06-08 Byk-Chemie GmbH Composés d'addition utilisables comme dispersant ou stabilisateur de dispersion, leur procédé de préparation, leur utilisation et les solidesrevêtus avec ces composés
EP0318999A2 (fr) 1987-12-04 1989-06-07 Byk-Chemie GmbH Composés d'addition utilisables comme dispersants et stabilisants de dispersion, leur procédé de préparation, leur utilisation et matières solides revêtues de ceux-ci
US5128393A (en) 1989-07-12 1992-07-07 E. I. Du Pont De Nemours And Company Imidazoline amine-epoxy adduct as a pigment dispersant
EP0747413A2 (fr) 1995-06-08 1996-12-11 Hoechst Aktiengesellschaft Dispersions aqueuses auto-émulsifiables à base de résines époxydes
DE19919482A1 (de) 1999-04-29 2000-11-02 Byk Chemie Gmbh Verfahren zur Herstellung eines thixotropie-Mittels und dessen Verwendung
DE10326147A1 (de) 2003-06-06 2005-03-03 Byk-Chemie Gmbh Epoxid-Addukte und deren Salze als Dispergiermittel
EP1593700A1 (fr) * 2004-05-07 2005-11-09 Byk-Chemie GmbH Composés d'addition utilisables comme dispersants et stabilisateurs de dispersion
WO2005113677A1 (fr) 2004-05-13 2005-12-01 Huntsman Petrochemical Corporation Emploi de polyetheralkanolamines en dents de scie dans des encres
EP1650246A1 (fr) * 2004-10-20 2006-04-26 Byk-Chemie GmbH Produit d addition epoxyde-amine alcoxyle et son usage
WO2008092687A1 (fr) 2007-01-31 2008-08-07 Byk-Chemie Gmbh Agent réticulant et dispersant universel à base de monoadduits d'isocyanate
DE102008010687A1 (de) * 2008-02-22 2009-09-03 Byk-Chemie Gmbh Netz- und Dispergiermittel, deren Herstellung und Verwendung

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050059794A1 (en) * 2003-09-12 2005-03-17 Glass Terry W. Water-soluble polyhydroxyaminoether and process for preparing the same
RU2256767C1 (ru) 2004-05-06 2005-07-20 Закрытое акционерное общество "Инвест ПромТорг" Высокогерметичное резьбовое соединение нефтепромысловых труб (варианты) и способы изготовления резьбового соединения этих труб (варианты)
KR101237170B1 (ko) * 2004-05-13 2013-02-25 헌츠만 페트로케미칼 엘엘씨 잉크 중의 빗-유사 폴리에테르알카놀아민
JP5029194B2 (ja) * 2007-07-31 2012-09-19 Ｄｉｃ株式会社 水性樹脂組成物
JP5231781B2 (ja) * 2007-10-25 2013-07-10 関西ペイント株式会社 水性樹脂組成物及びこれを含む水性塗料組成物
JP6146912B2 (ja) * 2010-04-23 2017-06-14 ルブリゾル アドバンスド マテリアルズ， インコーポレイテッド 分散剤組成物

Patent Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4710561A (en) 1985-11-27 1987-12-01 Kansai Paint Co., Ltd. [Poly]imidazoline adduct for electrocoating
DE3623296A1 (de) 1986-07-11 1988-01-14 Hoechst Ag Additionsverbindungen, verfahren zu ihrer herstellung und ihre verwendung
DE3623297A1 (de) 1986-07-11 1988-01-21 Hoechst Ag Additionsverbindungen, verfahren zu ihrer herstellung und ihre verwendung
EP0270126A2 (fr) 1986-12-05 1988-06-08 Byk-Chemie GmbH Composés d'addition utilisables comme dispersant ou stabilisateur de dispersion, leur procédé de préparation, leur utilisation et les solidesrevêtus avec ces composés
EP0318999A2 (fr) 1987-12-04 1989-06-07 Byk-Chemie GmbH Composés d'addition utilisables comme dispersants et stabilisants de dispersion, leur procédé de préparation, leur utilisation et matières solides revêtues de ceux-ci
US5128393A (en) 1989-07-12 1992-07-07 E. I. Du Pont De Nemours And Company Imidazoline amine-epoxy adduct as a pigment dispersant
EP0747413A2 (fr) 1995-06-08 1996-12-11 Hoechst Aktiengesellschaft Dispersions aqueuses auto-émulsifiables à base de résines époxydes
DE19919482A1 (de) 1999-04-29 2000-11-02 Byk Chemie Gmbh Verfahren zur Herstellung eines thixotropie-Mittels und dessen Verwendung
DE10326147A1 (de) 2003-06-06 2005-03-03 Byk-Chemie Gmbh Epoxid-Addukte und deren Salze als Dispergiermittel
EP1593700A1 (fr) * 2004-05-07 2005-11-09 Byk-Chemie GmbH Composés d'addition utilisables comme dispersants et stabilisateurs de dispersion
WO2005113677A1 (fr) 2004-05-13 2005-12-01 Huntsman Petrochemical Corporation Emploi de polyetheralkanolamines en dents de scie dans des encres
EP1650246A1 (fr) * 2004-10-20 2006-04-26 Byk-Chemie GmbH Produit d addition epoxyde-amine alcoxyle et son usage
WO2008092687A1 (fr) 2007-01-31 2008-08-07 Byk-Chemie Gmbh Agent réticulant et dispersant universel à base de monoadduits d'isocyanate
DE102007005720A1 (de) * 2007-01-31 2008-08-07 Byk-Chemie Gmbh Epoxid-Amin-Addukte als Dispergier- und Netzmittel
DE102008010687A1 (de) * 2008-02-22 2009-09-03 Byk-Chemie Gmbh Netz- und Dispergiermittel, deren Herstellung und Verwendung

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016059066A1 (fr) 2014-10-14 2016-04-21 Byk-Chemie Gmbh Produits d'addition époxy-amine pour la dispersion de matières solides
KR20170066491A (ko) * 2014-10-14 2017-06-14 비와이케이-케미 게엠베하 고형물을 분산시키기 위한 에폭시/아민 부가생성물
US10301486B2 (en) 2014-10-14 2019-05-28 Byk-Chemie Gmbh Epoxy/amine adducts for dispersing solids
KR102335792B1 (ko) 2014-10-14 2021-12-07 비와이케이-케미 게엠베하 고형물을 분산시키기 위한 에폭시/아민 부가생성물
WO2018184961A1 (fr) 2017-04-05 2018-10-11 Byk-Chemie Gmbh Produits d'addition monoépoxyde-monoamine en tant qu'agents mouillants et dispersants
US11560452B2 (en) 2017-04-05 2023-01-24 Byk-Chemie Gmbh Monoepoxide-monoamine adducts as wetting agents and dispersants
US11453748B2 (en) 2017-08-08 2022-09-27 Byk-Chemie Gmbh Amine functional compound

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EP2510034B1 (fr) 2014-03-12
US20130018126A1 (en) 2013-01-17
CN102652146A (zh) 2012-08-29
KR101801835B1 (ko) 2017-11-27
JP5685266B2 (ja) 2015-03-18
CN102652146B (zh) 2014-05-28
US9340641B2 (en) 2016-05-17
EP2333000A1 (fr) 2011-06-15
KR20120104234A (ko) 2012-09-20
EP2510034A1 (fr) 2012-10-17

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