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WO2007062953A1 - Resines aqueuses - Google Patents

Resines aqueuses Download PDF

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Publication number
WO2007062953A1
WO2007062953A1 PCT/EP2006/067967 EP2006067967W WO2007062953A1 WO 2007062953 A1 WO2007062953 A1 WO 2007062953A1 EP 2006067967 W EP2006067967 W EP 2006067967W WO 2007062953 A1 WO2007062953 A1 WO 2007062953A1
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WO
WIPO (PCT)
Prior art keywords
component
carbon atoms
resin dispersions
aqueous resin
dispersions according
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.)
Ceased
Application number
PCT/EP2006/067967
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German (de)
English (en)
Inventor
Patrick GLÖCKNER
Lutz Mindach
Friedrich Georg Schmidt
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.)
Evonik Operations GmbH
Original Assignee
Degussa GmbH
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Filing date
Publication date
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Publication of WO2007062953A1 publication Critical patent/WO2007062953A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C08G18/28—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
    • C08G18/54—Polycondensates of aldehydes
    • C08G18/548—Polycondensates of aldehydes with ketones
    • 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
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C08G12/34—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds and acyclic or carbocyclic compounds
    • C08G12/36—Ureas; Thioureas
    • 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
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/40—Chemically modified polycondensates
    • 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
    • C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
    • C08G18/0809—Manufacture of polymers containing ionic or ionogenic groups containing cationic or cationogenic groups
    • C08G18/0814—Manufacture of polymers containing ionic or ionogenic groups containing cationic or cationogenic groups containing ammonium groups or groups forming them
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/54—Polycondensates of aldehydes
    • C08G18/544—Polycondensates of aldehydes with nitrogen 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
    • C08G6/00—Condensation polymers of aldehydes or ketones only
    • C08G6/02—Condensation polymers of aldehydes or ketones only of aldehydes with ketones
    • 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
    • C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
    • C09D161/02—Condensation polymers of aldehydes or ketones only
    • 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
    • C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
    • C09D161/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C09D161/22—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
    • C09D161/24—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with urea or thiourea
    • 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
    • C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
    • C09D161/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C09D161/32—Modified amine-aldehyde condensates
    • 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
    • C09D175/04—Polyurethanes
    • 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
    • C09D175/04—Polyurethanes
    • C09D175/12—Polyurethanes from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group

Definitions

  • the present invention relates to aqueous ketone, ketone / aldehyde or urea / aldehyde resin dispersions, to a process for their preparation and to the use as main component, base component or additional component in coating materials, ballpoint pen pastes, pigment pastes, printing inks and inks, polishes, glazes, laminations, Fillers, cosmetics and / or sealants and insulating materials and adhesives.
  • water-soluble condensation products are listed, which are also obtained by joint reaction of ketones, aldehydes and acid groups introducing compounds. Examples of the latter are sulfites, amidosulfonic acid, aminoacetic acid and phosphorous acid salts.
  • DE-OS 34 06 473 and DE-OS 34 06 474 and EP-AO 154 835 describe processes for the preparation of stable aqueous dispersions of urea / aldehyde resins or ketone / (aldehyde) resins, after which the resin melt or their highly concentrated solution in the presence of organic protective colloids optionally dispersed in water with the addition of emulsifiers.
  • a disadvantage of this method is the fact that such organic protective colloids and emulsifiers, the application of the aqueous ketone / (aldehyde) - or Disturb urea / aldehyde resins in the coating sector.
  • the hydrophilic protective colloids and optionally emulsifiers remain in the coating and make them sensitive to moisture. The coating swells when exposed to moisture, loses its hardness and loses its anti-corrosion effect.
  • the object of the invention was to develop ketone, ketone / aldehyde or urea / aldehyde resin dispersions and a process for their preparation, which differs from the prior art by the use of novel emulsifiers.
  • the aqueous resin dispersions should be stable to hydrolysis or storage and should not have the disadvantages described above.
  • the moisture resistance of coating materials and adhesives containing the products of the invention should be high.
  • the resins should be suitable for use in paints and adhesives.
  • the ketone, ketone / aldehyde, urea / aldehyde resins of the invention thus modified and their hydrogenated secondary products give stable aqueous solutions, dilutions and dispersions, without requiring further neutralization.
  • aqueous systems of the invention are compared to those of the prior Technology already known systems completely saponification-stable and contain no further interfering additives z. B. in the form of other emulsifiers, protective colloids or electrolytes.
  • the present invention relates to aqueous resin dispersions, and a process for their preparation obtainable by reaction or proportionate reaction of
  • Suitable ketones for preparing the ketone-aldehyde resins and ketone resins are, Melhylelhylketonj ⁇ j ⁇ j ⁇ ui ⁇ iK ⁇ U ⁇ ⁇ lKcix heptanone-2, pentanone-3, methyl isobutyl ketone, Cyclopentanone, cyclododecanone, mixtures of 2,2,4- and 2,4,4-trimethylcyclopentanone, cycloheptanone and cyclooctanone, cyclohexanone and all alkyl-substituted cyclohexanones having one or more Alkyl radicals having a total of 1 to 8 hydrocarbon atoms, individually or in mixture.
  • alkyl-substituted cyclohexanones there may be mentioned 4-tert.-amylcyclohexanone, 2-sec.-butylcyclohexanone, 2-tert.-butylcyclohexanone, 4-tert.-butylcyclohexanone, 2-methylcyclohexanone and 3,3,5-trimethylcyclohexanone.
  • ketones Aldehyde resin syntheses as suitable called ketones, usually all C-H-acidic ketones are used. Preference is given to ketone-aldehyde resins based on the ketones acetophenone, cyclohexanone, 4-tert-butylcyclohexanone, 3,3,5-trimethylcyclohexanone and heptanone alone or in a mixture and ketone resins based on cyclohexanone.
  • aldehyde component of the ketone-aldehyde resins are in principle unsubstituted or branched aldehydes, such as.
  • formaldehyde acetaldehyde, n-butyraldehyde and / or iso-butyraldehyde, valeric aldehyde and dodecanal.
  • all the aldehydes mentioned in the literature as suitable for ketone resin syntheses can be used.
  • formaldehyde is used alone or in mixtures.
  • the required formaldehyde is usually used as about 20 to 40 wt .-% aqueous or alcoholic (eg, methanol or butanol) solution.
  • alcoholic eg, methanol or butanol
  • Other uses of formaldehyde such.
  • para-formaldehyde or trioxane are also possible.
  • Aromatic aldehydes, such as. B. benzaldehyde may also be included in admixture with formaldehyde.
  • Particularly preferred starting compounds for component A) acetophenone, cyclohexanone, 4-tert-butylcyclohexanone, 3,3,5-trimethylcyclohexanone and heptanone are used alone or in mixture and formaldehyde.
  • Hydrogenated secondary products of the resins of ketone and aldehyde are also used as component A).
  • the ketone-aldehyde resins described above are in the presence of a
  • Hydrogenated catalyst with hydrogen at pressures up to 300 bar is the Carbonyl group of the ketone-aldehyde resin converted into a secondary hydroxy group. Depending on the reaction conditions, a part of the hydroxy groups can be split off, so that methylene groups result. To illustrate, the following scheme is used:
  • n k + m
  • urea-aldehyde resins are used using a urea of the general formula (i)
  • R 1 and R 2 are hydrocarbon radicals (for example alkyl, aryl and / or alkylaryl radicals) in each case having up to 20 carbon atoms and / or formaldehyde is used.
  • Suitable aldehydes of the general formula (ii) are, for example, isobutyraldehyde, 2-methylpentanal, 2-ethylhexanal and 2-phenylpropanal and mixtures thereof. Isobutyraldehyde is preferred.
  • Formaldehyde may be in aqueous form, some or all of alcohols such. As methanol or ethanol may be used as paraformaldehyde and / or trioxane.
  • Typical methods of preparation and compositions are e.g. B. in DE 27 57 220, DE-OS 27 57 176 and EP 0 271 776 described.
  • Suitable as component B) are aromatic, aliphatic and / or cycloaliphatic di- and / or polyisocyanates.
  • diisocyanates examples include cyclohexane diisocyanate, methylcyclohexane diisocyanate, ethylcyclohexane diisocyanate, phenylene diisocyanate, propylcyclohexane diisocyanate,
  • polyisocyanates as component B are those by dimerization, trimerization, allophanatization, biuretization and / or urethanization the simple diisocyanates prepared compounds having more than two isocyanate groups per molecule, for example, the reaction products of these simple diisocyanates, such as. B. IPDI, TMDI, HDI and / or Hi 2 MDI with polyhydric alcohols (eg., Glycerol, trimethylolpropane, pentaerythritol) or polyhydric polyamines, or the triisocyanurates, 5 by trimerization of simple diisocyanates, such as IPDI, HDI and Hi 2 MDI, are available.
  • polyhydric alcohols eg., Glycerol, trimethylolpropane, pentaerythritol
  • polyhydric polyamines eg., trimethylolpropane, pentaerythritol
  • trimerization of simple diisocyanates
  • the introduction of the ionic liquid (IL, component C)) can be carried out by reacting a (poly) isocyanate and / or mixtures of different (poly) isocyanates with ILs with at least
  • component C) can also take place in-situ during the preparation of the pre-adduct.
  • ionic liquids are understood as meaning salts which have a melting point of not more than 100 ° C.
  • ILs Preferably used as IL are salts which have a melting temperature below
  • ionic liquids contain organic cations. Preference is given to ionic liquids which have one or more cations according to the following structures,
  • R 1, R 2 , R 3, R 4, R 5 and R 6 are the same or different and are hydrogen, hydroxy, alkoxy, sulfanyl (RS), NH 2 , NHR, NRR ', wherein R and R 'may be the same or different, substituted or unsubstituted alkyl groups having 1 to 8 carbon atoms, or halogen, in particular F, Cl, Br or I, where for cations of structure 10 and 11 one of Rl to R4, preferably all Rl to R4 preferably are not hydrogen; and / or a saturated or unsaturated, linear or branched aliphatic hydrocarbon radical having 1 to 40, preferably 1 to 30, preferably 1 to 20 carbon atoms which is substituted, for example with a hydroxy, alkyl having 1 to 8, preferably 1 to 4 carbon atoms and or halogen group, or may be unsubstituted; and / or a cycloaliphatic hydrocarbon radical having 5 to 30, preferably 5 to 10, preferably 5 to 8
  • the ionic liquids preferably have one or more anions selected from phosphate, halogen phosphates, in particular hexafluorophosphate, halides, especially chloride, alkyl phosphates, aryl phosphates, nitrate, sulfate, hydrogen sulfate, alkyl sulfates, aryl sulfates, perfluorinated alkyl and aryl sulfates, sulfonate, alkyl sulfonates, aryl sulfonates, perfluorinated alkyl and aryl sulfonates, in particular trifluoromethylsulfonate, tosylate, perchlorate, tetrachloroaluminate, heptachlorodialuminate, tetrafluoroborate, alkylborates, arylborates, amides, in particular perfluorinated amides, dicyanamide, saccharinate,
  • At least one salt which contains as cation an imidazolium, a pyridinium, an ammonium or phosphonium ion of the following structures:
  • R 1, R 2, R 3 and R 4 may be the same or different and a saturated or unsaturated, linear or branched aliphatic hydrocarbon radical having 1 to 40, preferably 1 to 30, preferably 1 to 20 carbon atoms substituted, for example, with a hydroxy, alkyl with 1 to 8, preferably 1 to 4 carbon atoms and / or halogen group, or may be unsubstituted; and / or a linear or branched aliphatic and / or cycloaliphatic and / or aromatic hydrocarbon radical having from 2 to 100 carbon atoms, preferably from 2 to 80 carbon atoms, particularly preferably from 2 to 40, interrupted by one or more heteroatoms (oxygen, NH, NCH 3 ) Carbon atoms which may be substituted, for example, with amino, hydroxy, alkyl of 1 to 8, preferably 1 to 4 carbon atoms and / or halogen groups, or may be unsubstituted; and / or a one or more functionalities selected from the group
  • a mixture of at least two different ionic liquids can also be used as component C).
  • the IL can have at least two different anions and / or two different cations.
  • reaction of A) with B) and C) can be carried out in one or two stages, wherein in a two-stage procedure, first component B) is reacted with C) in such a way that at least one free isocyanate group is retained, which is then mixed with component A ) can be implemented further.
  • the reaction can be carried out in bulk or preferably in the presence of a suitable auxiliary solvent.
  • Preferred solids contents when using an auxiliary solvent are 50 to 95% by mass, more preferably 55 to 80% by mass.
  • Suitable auxiliary solvents are either preferably those which have a boiling point below 100 0 C at 1013 hPa and can be removed by distillation from the final aqueous system again completely to a residual content of 0.5 Mass ⁇ and re-use, such as acetone, methyl ethyl ketone or tetrahydrofuran , or possibly higher boiling, which remain in the aqueous system, such as butyl glycol, butyl diglycol or N-methylpyrrolidone.
  • the below 100 0 C boiling auxiliary solvents are therefore preferred because they allow the production of purely aqueous, solvent-free and therefore environmentally friendly dispersions.
  • An advantage of the method according to the invention lies precisely in the fact that it is possible completely to dispense with organic solvents in the finished aqueous resin dispersion and still obtain solids-rich, stable dispersions.
  • a hydroxy-functional ionic liquid (component C)) with one mole of diisocyanate (component B)) is optionally reacted using a suitable solvent and a suitable catalyst such that an isocyanate group remains unreacted.
  • the product produced is added to a solution or melt of the hydroxyl-containing ketone, ketone-aldehyde, urea-aldehyde resins or their hydrogenated secondary products (A) and reacted.
  • the temperature of the reaction is selected. There have in all reaction steps, temperatures from 30 to 125 0 C, preferably between 50 and 100 0 C proven.
  • the reaction product can be dispersed in water without further neutralization.
  • the solvent optionally present can be separated off after the end of the reaction, in which case a solution until dispersion of the product according to the invention is then generally obtained.
  • a di- or polyhydroxy-functional ionic liquid (component C)) with one mole of diisocyanate (component B)) per hydroxyl group e.g. one mole of a di- or polyhydroxy-functional ionic liquid (component C)) with one mole of diisocyanate (component B)) per hydroxyl group, if appropriate using a suitable solvent and a suitable catalyst so that an isocyanate group based on the OH functionality remains unreacted.
  • a dihydroxy-functional ionic liquid two isocyanate groups remain unreacted.
  • the product produced becomes a solution or melt of the hydroxy group-containing Ketone, ketone-aldehyde, urea-aldehyde or their hydrogenated secondary products (A) and reacted.
  • the temperature of the reaction is selected. There have in all reaction steps, temperatures from 30 to 125 0 C, preferably between 50 and 100 0 C proven.
  • the reaction product can be dispersed in water without further neutralization.
  • the solvent optionally present can be separated off after the end of the reaction, in which case a solution until dispersion of the product according to the invention is then generally obtained.
  • a suitable catalyst for the preparation of the resins of the invention can be used.
  • Suitable are all known in the literature compounds that accelerate an NH or OH-NC O-reaction, such as.
  • As catalysts based on the metals tin, bismuth, zirconium, titanium, zinc, iron and / or aluminum, such as.
  • Amines for example 1,4-diazabicyclo [2.2.2] octane (DABCO), l, 8-diazabicyclo [5.4.0] undec-7-ene (DBU), N 5 N- dimethylcyclohexylamine (DMCA) or l, 5-diazabicyclo [2.3.0] non-5-en (DBN).
  • DABCO 1,4-diazabicyclo [2.2.2] octane
  • DBU 8-diazabicyclo [5.4.0] undec-7-ene
  • DMCA N 5 N- dimethylcyclohexylamine
  • DBN 5-diazabicyclo [2.3.0] non-5-en
  • chain terminators can be used to terminate the reaction.
  • Suitable for this purpose are mono-functional compounds such as amines or alcohols. Examples include alkyl, dialkylamines, arylamines such as butylamine, benzylamine, dibutylamine, diethylamine, aliphatic and / or aromatic alcohols such as ethanol, butanol.
  • the reaction product of A), B) and C) may optionally be combined with other non-hydrophilic resins or other water-soluble or water-dilutable components and then dispersed together. This measure makes it technically advantageous to achieve a high solids content of the dispersions of more than 35% by mass, preferably from 35 to 40% by mass, to about 50% by mass.
  • the resin dispersions of the invention are at least 6 weeks at 50 0 C sedimentation stable.
  • the reaction product of A), B) and C) may other excipients and additives selected from inhibitors, surfactants, oxygen and / or radical scavengers, catalysts, sunscreens, Klarb brighteners, photosensitizers and initiators, additives to influence theological Properties such.
  • thermoplastic additives dyes, pigments, matting agents, fire retardants, fillers and / or propellants.
  • novel resin dispersions are suitable as the main component, base component or additional component in coating materials, ballpoint pen pastes, pigment pastes, printing inks and inks, polishes, glazes, laminations, fillers, cosmetics and / or sealants and insulating materials and adhesives.
  • Example 1 a) reaction of a polyisocvanate B) with an IL C) and subsequent reaction with a ketone-aldehyde resin A)
  • Example 2 a) Reaction of a polyisocyanate B) with an IL C) and subsequent reaction with a ketone-aldehyde resin A)
  • 250 g of the solution prepared under 1) are dispersed at room temperature by addition of 350 g of demineralized water with vigorous stirring.
  • the auxiliary solvent acetone and water are removed in vacuo, and there is a storage-stable, white resin dispersion having a solids content of about 34% by mass, a pH of 5.6 and a viscosity below 50 mPas.
  • Example of a coating composition Example of a coating composition:
  • DI water fully demineralized water
  • Test panels Coating structure (spray application) on phosphated steel sheet: cathodic dip coating, coating materials according to the examples, metallic basecoat, clearcoat Drying conditions: flash-off time approx. 10 min, then 20 min 16O 0 C
  • the coatings were exposed to 100 ° C hot steam for 30 minutes. While the coating of the comparative example already swells after 20 minutes, the coating materials according to Examples A and B were unchanged after 30 minutes. This results in an improved corrosion protection effect.
  • the dispersions are present in the coating composition in ranges of 1 and 90, preferably between 2 and 50, more preferably between 3 and 30 wt .-%.

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

Abstract

L'invention concerne des dispersions de résines aqueuses obtenues par réaction ou réaction proportionnelle de A) des résines de cétones contenant des groupes hydroxy, de cétone/aldéhyde, d'urée/aldéhyde ou leurs dérivés hydrogénés et de B) au moins un diisocyanate ou un polyisocyanate aromatique, aliphatique et/ou cycloaliphatique et au moins un liquide ionique présentant une fonction réactive vis à vis de groupes isocyanate C) et d'autres groupes fonctionnels, puis par incorporation ultérieure de la résine dans de l'eau, un procédé de fabrication de ces dispersions, ainsi que leur utilisation en tant que composant principal, composant de base ou additif dans des matériaux de revêtement, des pâtes pour stylos à bille, des pâtes de pigment, des colorants et des encres pour impression, des produits à polir, des vernis, des charges, des produits cosmétiques et/ou des matériaux de scellement et d'isolation, ainsi que des adhésifs.
PCT/EP2006/067967 2005-12-03 2006-10-31 Resines aqueuses Ceased WO2007062953A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200510057853 DE102005057853A1 (de) 2005-12-03 2005-12-03 Wässrige Harze
DE102005057853.5 2005-12-03

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WO2007062953A1 true WO2007062953A1 (fr) 2007-06-07

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WO2011061314A1 (fr) 2009-11-23 2011-05-26 Basf Se Catalyseurs pour des masses de revêtement à base de polyuréthane
US9493660B2 (en) 2007-08-16 2016-11-15 Basf Coatings Gmbh Use of bismuth subnitrate in electro-dipping paints
US9963538B2 (en) 2013-01-07 2018-05-08 Basf Se Catalysts for polyurethane coating compounds
CN116874683A (zh) * 2023-09-07 2023-10-13 广东腐蚀科学与技术创新研究院 一种室温自交联聚阳离子液体改性水性聚氨酯分散体及其制备方法和其应用

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DE102008016220A1 (de) 2008-03-27 2009-10-01 Basf Coatings Ag Elektrotauchlacke enthaltend Polymethylenharnstoff
CN109111559A (zh) * 2018-07-25 2019-01-01 禾丰新材料科技有限公司 水性聚酮树脂乳液及其制备方法和应用
CN109761647B (zh) * 2019-03-19 2021-11-23 重庆唯美陶瓷有限公司 一种钛系复层花釉陶瓷砖及其制备方法
CN113265037B (zh) * 2021-05-17 2023-03-24 万华化学（宁波）有限公司 一种多异氰酸酯组合物及其制备方法和应用

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EP0838486A1 (fr) * 1996-10-23 1998-04-29 Hüls Aktiengesellschaft Dispersions aqueuses de résine
WO2000058547A1 (fr) * 1999-03-29 2000-10-05 Bayer Aktiengesellschaft Agents de traitement pour textiles, procede de preparation desdits agents et leur utilisation

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9493660B2 (en) 2007-08-16 2016-11-15 Basf Coatings Gmbh Use of bismuth subnitrate in electro-dipping paints
US10975252B2 (en) 2007-08-16 2021-04-13 Basf Coatings Gmbh Use of bismuth subnitrate in electro-dipping paints
WO2011061314A1 (fr) 2009-11-23 2011-05-26 Basf Se Catalyseurs pour des masses de revêtement à base de polyuréthane
US8709544B2 (en) 2009-11-23 2014-04-29 Basf Se Catalysts for polyurethane coating compounds
US9963538B2 (en) 2013-01-07 2018-05-08 Basf Se Catalysts for polyurethane coating compounds
CN116874683A (zh) * 2023-09-07 2023-10-13 广东腐蚀科学与技术创新研究院 一种室温自交联聚阳离子液体改性水性聚氨酯分散体及其制备方法和其应用
CN116874683B (zh) * 2023-09-07 2023-12-08 广东腐蚀科学与技术创新研究院 一种室温自交联聚阳离子液体改性水性聚氨酯分散体及其制备方法和其应用

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