WO2007077058A1 - Resines contenant des liquides ioniques - Google Patents

Resines contenant des liquides ioniques Download PDF

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Publication number
WO2007077058A1
WO2007077058A1 PCT/EP2006/068866 EP2006068866W WO2007077058A1 WO 2007077058 A1 WO2007077058 A1 WO 2007077058A1 EP 2006068866 W EP2006068866 W EP 2006068866W WO 2007077058 A1 WO2007077058 A1 WO 2007077058A1
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WIPO (PCT)
Prior art keywords
resins
component
carbon atoms
resins according
alkyl
Prior art date
Application number
PCT/EP2006/068866
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German (de)
English (en)
Inventor
Patrick GLÖCKNER
Friedrich Georg Schmidt
Original Assignee
Degussa Ag
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Publication of WO2007077058A1 publication Critical patent/WO2007077058A1/fr

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Classifications

    • 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
    • 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
    • C08G18/28—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
    • C08G18/285—Nitrogen containing 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
    • C08G18/3842—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the 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
    • C08G18/28—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
    • 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

Definitions

  • the present invention relates to resins based on ionic liquids and ketone, ketone / aldehyde, urea / aldehyde resins and their hydrogenated derivatives, a process for their preparation and the use as main component, base component or additive component in aqueous, solvent-borne and solvent-free coating materials, Ballpoint pen pastes, pigment pastes, printing inks and inks, polishes, glazes, laminations, fillers, cosmetics and / or sealants and insulating materials, and adhesives and plastics.
  • Ketone-formaldehyde resins have been known for a long time. Process for the preparation are for. As described in DE 33 24 287, US-PS 2,540,885, US-PS 2,540,886, DE-PS 11 55 909, DL-PS 12 433, DE-PS 13 00 256 and DE-PS 12 56 898 The hydrogenation of these resins has been practiced for a long time (DE 826 974, DE 8 70 022, DE 32 41 735, JP 11012338, US 6,222,009). Urea aldehyde resins are e.g. in DE 27 57 220, DE-OS 27 57 176 and EP 0 271 776 described.
  • the object of the invention was to modify ketone, ketone / aldehyde or urea / aldehyde resins and / or their hydrogenated secondary products so that they stand out from the stand Differentiate the technology by using novel compounds and to develop a process for their preparation.
  • the resins are said to be stable to saponification and in particular to have lower brittleness than the prior art resins without, however, degrading properties such as gloss, hardness or scratch resistance.
  • adhesion properties of coating materials and adhesives should be supported by using these resins.
  • the resins are stable to hydrolysis and have less brittleness than the starting resins. Adhesive properties of coating materials and adhesives are positively influenced by using the resins according to the invention, wherein gloss, hardness and scratch resistance are retained.
  • the present invention provides resins and a process for their preparation obtainable by reaction or proportionate reaction of
  • Suitable ketones for the preparation of the ketone and ketone aldehyde resins are all ketones, in particular acetone, acetophenone, methyl ethyl ketone, tert-butyl methyl ketone, heptanone-2, pentanone-3, methyl isobutyl ketone, cyclopentanone, cyclododecanone, mixtures from 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 admixture.
  • 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 usually all C-H-acidic ketones.
  • suitable ketones usually all C-H-acidic ketones.
  • 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.
  • 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 hydrogenated in the presence of a catalyst with hydrogen at pressures of up to 300 bar.
  • the carbonyl group of the ketone-aldehyde resin is converted into a secondary hydroxy group.
  • a part of the hydroxy groups can be split off, so that methylene groups result.
  • the following scheme is used:
  • n k + m
  • urea-aldehyde resins are used using a urea of the general formula (i)
  • hydrocarbon radicals eg., Alkyl, aryl and / or alkylaryl radicals each having up to 20 carbon atoms and / or formaldehyde 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 and polyisocyanates examples include cyclohexane diisocyanate, methylcyclohexane diisocyanate, ethylcyclohexane diisocyanate, phenylene diisocyanate,
  • Another preferred class of polyisocyanates as component B) are the compounds prepared by dimerization, trimerization, allophanatization, biuretization and / or urethanization of simple diisocyanates having more than two isocyanate groups per molecule, for example the reaction products of these simple diisocyanates, such.
  • IPDI, TMDI, HDI and / or Hi 2 MDI with polyhydric alcohols eg., Glycerol, trimethylolpropane, pentaerythritol
  • polyhydric polyamines eg., Glycerol, trimethylolpropane, pentaerythritol
  • triisocyanurates obtained by trimerization of simple diisocyanates such as IPDI, HDI and Hi 2 MDI
  • 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 having at least one isocyanate-reactive function, for. B. OH, NH and carried out with at least one further functional group in the way that at least one NCO function is maintained and subsequent reaction with A).
  • ILs having at least one isocyanate-reactive function
  • B. OH, NH OH, NH
  • the introduction of component C) can also be carried out 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 which have a melting temperature below 75 0 C, preferably below 5O 0 C, more preferably below 2O 0 C hold.
  • 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
  • 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
  • reaction of A) with B) and C) can be carried out in one or two stages, wherein in a two-stage procedure, component B) is first reacted with C) in such a way that at least one free isocyanate group is retained, which is then reacted with component A). can be implemented further.
  • the reaction can be carried out in bulk or in the presence of a suitable solvent.
  • Preferred solids contents when using a solvent 40 to 95% by mass, particularly preferably 50 to 80% by mass.
  • Suitable solvents are those which are inert to isocyanates. Preference is given, e.g. Acetates, ketones, ethers, glycol ethers, aliphatics, aromatics, ionic liquids without isocyanate-reactive groups alone or in mixture. However, it is also possible to use what are known as reactive diluents which are customarily used in UV-curable coating materials, such as e.g. Acrylate-functionalized mono-, di- or higher alcohols.
  • a hydroxy-functional ionic liquid component C
  • diisocyanate component B
  • the product produced is added to a solution or melt of the hydroxyl-containing ketone, ketone-aldehyde, urea-aldehyde or their hydrogenated derivatives (A) and reacted.
  • component C hydroxy-functional ionic liquid
  • component B diisocyanate
  • 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.
  • 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-NCO 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, 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-dimethylcyclohexylamine
  • DBN 5-diazabicyclo [2.3.0] non-5-en
  • the reaction product from A), B) and C) can be further auxiliaries and additives selected from organic solvents, water, inhibitors, surface-active substances, oxygen and / or radical scavengers, catalysts, light stabilizers, color brighteners, photosensitizers and initiators, additives for Influencing theological properties such.
  • thermoplastic additives dyes, pigments, matting agents, fire retardants, fillers and / or propellants.
  • the glass transition temperature (T g ) of the reaction products of A) and B) and C) is between -30 and 12O 0 C, preferably between -10 and 100 0 C, more preferably between 0 and 8O 0 C.
  • the molecular weight M n of the inventive Products is between 500 and 30,000 g / mol. preferably between 750 and 10,000 g / mol, more preferably between 800 and 5,000 g / mol.
  • the molecular weight M w of the products according to the invention is between 1,000 and 80,000 g / mol. preferably between 1,500 and 20,000 g / mol, more preferably between 1,500 and 10,000 g / mol.
  • the Gardner color number (50% in ethyl acetate) of the products according to the invention is between 0 and 10, preferably between 0 and 7, particularly preferably between 0 and 5.
  • the resins according to the invention are stable to hydrolysis, have a low brittleness and are suitable as the main component, base component or additional component in aqueous, solvent-based and solvent-free coating materials, ballpoint pen pastes,
  • Pigment pastes printing inks and inks, polishes, glazes, fillers,
  • Cosmetic articles and / or sealants and insulating materials and adhesives and plastics in particular for improving adhesion properties with good gloss, good hardness and scratch resistance.
  • Example of a coating composition Example of a coating composition:
  • ABS acrylonitrile-butadiene-styrene copolymer
  • PC polycarbonate
  • PE polyethylene
  • PVC polyvinyl chloride

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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)
  • General Chemical & Material Sciences (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention concerne des résines et un procédé de production associé, lesdites résines étant obtenues par la mise en réaction ou en réaction proportionnelle de A) une résine de cétones, de résine de cétone / aldéhyde et de résine d'urée / aldéhyde contenant des groupes hydroxy et/ou leur produits obtenus hydrogénés avec B) au moins un diisocyanate ou polyisocyanate aromatique, aliphatique et/ou cycloaliphatique et C) au moins un liquide ionique, qui présente au moins une fonction réactive vis-à-vis des groupes isocyanates. L'invention concerne également l'utilisation desdites résines en tant que constituant principal, constituant de base ou constituant supplémentaire dans des substances de revêtement aqueuses contenant ou exemptes de solvants, dans des pâtes pour stylos à billes, des pâtes de pigments, des encres d'impression et des encres, des vernis, des lasures, des charges, des cosmétiques et/ou des matériaux étanches et isolants, et des matériaux adhésifs et synthétiques.
PCT/EP2006/068866 2006-01-03 2006-11-24 Resines contenant des liquides ioniques WO2007077058A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006000648.8 2006-01-03
DE200610000648 DE102006000648A1 (de) 2006-01-03 2006-01-03 Ionische Flüssigkeiten enthaltene Harze

Publications (1)

Publication Number Publication Date
WO2007077058A1 true WO2007077058A1 (fr) 2007-07-12

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CN (1) CN101003608A (fr)
DE (1) DE102006000648A1 (fr)
WO (1) WO2007077058A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102590315A (zh) * 2007-07-19 2012-07-18 郡是株式会社 氢气传感器及其制造方法
WO2012173982A1 (fr) * 2011-06-16 2012-12-20 Sabic Innovative Plastics Ip B.V. Compositions ayant un coefficient de frottement réduit, leur procédé de fabrication et articles les comprenant
CN103173261A (zh) * 2011-12-23 2013-06-26 中国科学院兰州化学物理研究所 羟基咪唑功能化离子液体润滑剂及其制备方法
PL422051A1 (pl) * 2017-06-28 2019-01-02 Politechnika Łódzka Kompozycja na pianki poliuretanowe o strukturze porowatej i polepszonych właściwościach mechanicznych, zastosowanie kompozycji
CN110564354A (zh) * 2019-07-25 2019-12-13 启东东岳化工有限公司 一种辊涂用高初粘力的聚氨酯粘合剂及其制备方法

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CN109180888B (zh) * 2018-08-16 2021-03-12 山东阳谷华泰化工股份有限公司 一种改性烷基酚-乙醛树脂及其制备方法
CN110170077B (zh) * 2019-03-26 2021-09-28 南京理工大学 一种聚离子型生物润滑剂及其制备方法
CN110003411B (zh) * 2019-04-03 2021-05-07 北京化工大学 缩聚大分子光引发剂的制备方法及制备得到的光引发剂
CN116813917A (zh) * 2022-10-31 2023-09-29 张燕 一种超低温环氧密封胶用固化剂及其制备的密封胶

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0541289A1 (fr) * 1991-11-01 1993-05-12 Witco Corporation Procédés de préparation de compositions de polyuréthanes cationiques et de sels d'ammonium quaternaires
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

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0541289A1 (fr) * 1991-11-01 1993-05-12 Witco Corporation Procédés de préparation de compositions de polyuréthanes cationiques et de sels d'ammonium quaternaires
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
CN102590315A (zh) * 2007-07-19 2012-07-18 郡是株式会社 氢气传感器及其制造方法
WO2012173982A1 (fr) * 2011-06-16 2012-12-20 Sabic Innovative Plastics Ip B.V. Compositions ayant un coefficient de frottement réduit, leur procédé de fabrication et articles les comprenant
US9169371B2 (en) 2011-06-16 2015-10-27 Sabic Global Technologies B.V. Compositions having reduced frictional coefficient, method of manufacture thereof and articles comprising the same
CN103173261A (zh) * 2011-12-23 2013-06-26 中国科学院兰州化学物理研究所 羟基咪唑功能化离子液体润滑剂及其制备方法
CN103173261B (zh) * 2011-12-23 2015-02-25 中国科学院兰州化学物理研究所 羟基咪唑功能化离子液体润滑剂及其制备方法
PL422051A1 (pl) * 2017-06-28 2019-01-02 Politechnika Łódzka Kompozycja na pianki poliuretanowe o strukturze porowatej i polepszonych właściwościach mechanicznych, zastosowanie kompozycji
CN110564354A (zh) * 2019-07-25 2019-12-13 启东东岳化工有限公司 一种辊涂用高初粘力的聚氨酯粘合剂及其制备方法

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