WO1998005696A1 - Dispersions aqueuses, leur preparation et leur utilisation comme liants pour peintures - Google Patents

Dispersions aqueuses, leur preparation et leur utilisation comme liants pour peintures Download PDF

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Publication number
WO1998005696A1
WO1998005696A1 PCT/EP1997/003908 EP9703908W WO9805696A1 WO 1998005696 A1 WO1998005696 A1 WO 1998005696A1 EP 9703908 W EP9703908 W EP 9703908W WO 9805696 A1 WO9805696 A1 WO 9805696A1
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Prior art keywords
weight
molecular weight
groups
dispersions
functionality
Prior art date
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PCT/EP1997/003908
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German (de)
English (en)
Inventor
Reinhold Hecht
Lutz Hoppe
Erhard Lühmann
Wolfgang Dannhorn
Original Assignee
Wolff Walsrode Ag
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Publication date
Application filed by Wolff Walsrode Ag filed Critical Wolff Walsrode Ag
Priority to AU39404/97A priority Critical patent/AU3940497A/en
Publication of WO1998005696A1 publication Critical patent/WO1998005696A1/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
    • C09D175/02—Polyureas
    • 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
    • C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
    • C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt 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
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation 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
    • C08G18/65—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
    • C08G18/6633—Compounds of group C08G18/42
    • C08G18/6659—Compounds of group C08G18/42 with compounds of group C08G18/34

Definitions

  • Aqueous dispersions their production and use as paint binders
  • the present invention relates to new aqueous dispersions of polyurethane polyureas for the production of ethanol-resistant coatings.
  • Polyurethane polyureas which were applied by organic solvent systems, are characterized by outstanding properties, such as. B chemical resistance, abrasion resistance, toughness, tensile strength and elasticity. They are therefore used in a variety of commercial applications, such as. B. as adhesives or coating agents for various substrates such as textiles, plastics, wood. Glass fibers, leather and metals. When drying the coatings, however, problems arise which are caused by the emission of the organic solvents.
  • An improvement could, for. B. can be achieved by incorporating groups with an emulsifier function into the polymer chain.
  • These so-called internal emulsifiers are either ionic and / or nonionic in nature. Examples of ionic internal emulsifiers are described in US 3,479,310 and examples of nonionic emulsifiers and the like. a. in the patents US 3 905 929 and US 4 190 566. The use of internal emulsifiers leads to dispersions with improved stabilities and a reduced content of hydrophilic structural components. The resulting
  • Coatings are characterized by improved water resistance and less loss of mechanical stability in the swollen state. But also these dispersions in no way meet the requirement for a chemical-resistant coating and in particular a coating with good ethanol strength
  • Coatings with high chemical resistance based on aqueous polyurethane dispersions are obtained if the polymers dispersed in water still have functional groups. As described in EP 0 669 352, these can then be used for crosslinking reactions by adding a suitable co-resin. In practice, such two-component systems can only be formulated with considerable effort and have a limited pot life.
  • polyurethane-polyurea dispersions which already provide films with improved chemical resistance after physical drying, are based on polycarbonate diols.
  • polycarbonate diols are very expensive starting materials, and the coatings are changed or destroyed by ethanol in a test according to DIN 68861, so that they are used alone
  • Comparable polyurethane polyurea dispersions based on cheaper starting materials e.g. Polyester polyols could be produced by incorporating special dimeric fatty acids. Such dispersions are e.g. described in EP 0 643 734. The chemical resistance could only be improved slightly compared to the dispersions based on polycarbonate diol. Another problem is that the dimeric fatty acids can cause embrittlement of the coatings.
  • the aim of the present invention was therefore to produce polyurethane-polyurea dispersions which, after physical drying without the addition of crosslinking agents and as the sole binder, provide films with a significantly improved chemical and in particular an improved resistance to ethanol.
  • the object was surprisingly achieved by providing the dispersions according to the invention described in more detail below, the Particularly outstanding ethanol resistance of the resulting coatings can be attributed to the use of substances known per se in a preferred combination of quantities.
  • the invention relates to polyurethane-polyurea dispersions, built up by polyaddition of:
  • (E) 30 to 70% by weight, preferably 40 to 60% by weight, of one or more polyisocyanates, at least 70% by weight of the polyisocyanate component consisting of one or more cycloaliphatic diisocyanates,
  • component (F) 0.5 to 10% by weight of a mixture of one or more diamines with a polyamine of functionality> 2, where at least 20% by weight of component (F) consists of the polyamine of functionality> 2.
  • the percentages of components (A) to (F) add up to 100%.
  • the present invention furthermore relates to the use of the new polyurethane-polyurea dispersions as paint binders for the coating of any substrates
  • Linear and / or weakly branched polyester polyols with a molecular weight of 500 to 6000 and in a particularly preferred embodiment from 750 to 3000 are used as component A. These are reaction products of low molecular weight polyols with low molecular weight polycarboxylic acids
  • Suitable polyols or polyol mixtures for the construction of polyesters containing hydroxyl groups are, for example, ethylene glycol, propylene glycol, 1,4-butanediol, 1,6-hexanediol, diethylene glycol, tylenethylene glycol, neopentyl glycol, 1,4-bis (hydroxymethyl) cyclohexane or dipropylene glycol
  • Polyols which can be used in part to introduce the branches into the polyester molecule are, for example, glycene, tmethylolpropane or pentaerythritol suitable. 1, 6-Hexanediol, neopentylglycol and tmethylolpropane are particularly preferred
  • polycarboxylic acids can be aliphatic, cycloaliphatic, aromatic and / or heterocratic in nature.
  • corresponding polycarboxylic acid anhydrides or polycarboxylic acid esters with lower alcohols can also be used. Examples include succinic acid, adipic acid,
  • Sebacic acid, azelaic acid, phthalic acid, isophthalic acid, phthalic anhydride, tetrahydrophthalic anhydride, glutaric anhydride, maleic acid, maleic anhydride, fumaric acid or dimethyl terephthalate is particularly preferred
  • Component (A) generally has an average hydroxyl functionality of 2.0, ie 2 OH groups per molecule, through the use or the proportionate When using weakly branched polyester polyols, the average hydroxyl functionality can be increased to a maximum value of 2.5
  • the low molecular weight polyols mentioned under point (B) with a molecular weight of ⁇ 500 are ahphatic, cycloaliphatic, aromatic and / or heterocyclic compounds, as have already been mentioned under point (A) for the construction of the polyester polyols.
  • Particularly preferred polyol le are neopentyl glycol and trimethylol propane
  • the starting component (C) is usually at least one
  • Hydroxycarboxylic acid and / or aminocarboxylic acid and / or aminosulfonic acid and / or hydroxysulfonic acid are incorporated into the prepolymer via the amino and / or hydroxyl groups which are reactive towards isocyanates by neutralizing the carboxyl groups and / or the sulfonic acid groups with organic and / or inorganic bases these compounds have dispersing properties
  • component (C) malic acid, glycolic acid, glycine, taurine, aminocaproic acid and 2-amino-ethylammosulfonic acid.
  • the preferred components (C) include 2,2-bis (hydroxymethyl) alkane monocarboxylic acids with a total of 5 to 8 carbon atoms, ie compounds of the general formula
  • R represents an alkyl radical having 1 to 4 carbon atoms.
  • a particularly preferred structural component (C) is 2,2-dimethylolpropionic acid
  • the starting component (D) is nonionic, hydrophilic polyethylene glycols which have one or two hydroxyl groups it is mono- or dihydric polyether alcohols in the molecular weight range from 600 to 3000, as are obtained in a manner known per se by alkoxylation of mono- or dihydric alcohols as starter molecules, ethylene oxide or mixtures of ethylene oxide with up to 40% by weight as alkylene oxides (based on the total weight of the alkylene oxides) of propylene oxide.
  • the corresponding amino-functional derivatives known as Jeffamin M or Jeffamin D series (commercial products from Huntsman), are also suitable components (D)
  • components (C) and / or components (D) must be adjusted so that the dispersibility of the polyurethane polyureas in water is ensured.
  • the use of component (D) is completely dispensed with and the hydrophilicity required for the dispersion ensured solely by the use of component (C)
  • the amount of anionic groups incorporated is dimensioned such that a maximum of 100 milliequivalents per 100 g of solid ionic groups are present in the polyurethane polyurea ultimately obtained
  • the compounds (E) required for the polyaddition reaction are aphatic, cycloahphatic and / or aromatic polyisocyanates
  • the polyisocyanate component (E) consists of cycloaliphatic dnsocyanates.
  • cycloaliphatic diisocyanates such as isophorone diisocyanate (IPDI), 4,4'-dicyclohexylmethane diisocyanate and / or 1 , 4- or 1, 3-cyclohexane diisocyanate used
  • polyisocyanates examples include 1,6-hexamethylene diisocyanate (HDI), tetramethyl endiisocyanate, 2,3,3-T ⁇ -methylhexamethylene di-isocyanate, 1,4-phenylenedinsocyanate, 2,6- and 2.4 -Toluene d ⁇ socyanat, 1,5 naphthylene diisocyanate, 2,4'- and 4,4'-diphenylmethane diisocyanate It is of course also possible to use those known per se in polyurethane chemistry higher-proportionate polyisocyanates or modified polyisocyanates known per se, for example carbodiimide groups, allophanate groups, isocyanurate groups, urethane groups and / or polyisocyanates having biuret groups.
  • HDI 1,6-hexamethylene diisocyanate
  • tetramethyl endiisocyanate 2,3,3-T ⁇ -methylhexamethylene di-isocyanate
  • Components (A) to (E) are placed in a reactor and converted to an NCO-containing prepolymer under anhydrous conditions in a temperature range from 30 to 30 ° C.
  • the ratio of equivalents of isocyanate groups to compounds reactive towards isocyanate groups is 1.1: 1 to 3: 1, preferably 1.5: 1 to 2: 1.
  • Carboxy groups which are introduced into the prepolymer are not taken into account.
  • the isocyanate polyaddition reaction can take place in the presence of catalysts known in polyurethane chemistry, such as, for example, organo-tin compounds.
  • an organic one can be used before, during or after the prepolymer production
  • Solvents are used to control viscosity.
  • Suitable solvents are e.g. As acetone, 2-butanone, tetrahydrofuran, dioxane, dimethylformamide, N-methyl-2-pyrrolidone (NMP), ethyl acetate, alkyl ethers of ethylene and propylene glycol and aromatic hydrocarbons.
  • NMP N-methyl-2-pyrrolidone
  • ethyl acetate alkyl ethers of ethylene and propylene glycol and aromatic hydrocarbons.
  • the use of water-miscible solvents is preferred.
  • Low-boiling solvents such as. B. acetone used, they can be removed from the resulting polyurethane-polyurea dispersions by distillation, and completely solvent-free dispersions are obtained.
  • solvents with higher boiling points than water, such as. B. NMP used these solvents remain in the polyurethane-polyurea dispersions and accelerate the film formation of the dispersed particles as a coalescence aid
  • the potential ionic groups present in the prepolymer must be converted into ionic groups by neutralization.
  • neutralization especially when using carboxyl group-containing structural components (C), preferably tertiary amines.
  • tertiary amines are, for example, triethylamine, tri-n-butylamine,
  • N-methylmorpholine N, N-dimethylethanolamine, N-methylpiperidine, N-methylpiperazine and triethanolamine.
  • inorganic bases such as sodium hydroxide or potassium hydroxide as a neutralizing agent is also possible, although less preferred. Mention should also be made of the possibility of using component (C) in neutralized form in the preparation of the prepolymer.
  • Neutralization of the potential ionic groups ensures that the formation of stable aqueous dispersions is ensured.
  • at least 80%, but preferably 100%, of the potential ionic groups are converted into ionic groups by neutralization.
  • the neutralization reaction usually takes place at
  • the neutralized NCO-containing prepolymers are converted into aqueous dispersions by the methods known in polyurethane chemistry.
  • One possibility is to add the dispersing water, which contains component (F), to the prepolymer.
  • the organic prepolymer first forms the continuous phase.
  • the phase reverses and the water becomes a continuous phase.
  • the neutralized prepolymer is added to the dispersing water.
  • Component (F) can be initially introduced into the dispersing water or, alternatively, can only be added after the prepolymer has been dispersed.
  • the dispersing step is preferably carried out in a temperature range from 20 to 40 ° C.
  • the dispersibility of the prepolymers in water can be improved by the additional use of external emulsifiers.
  • Component (F) consists of a mixture of one or more diamines with a polyamine with functionality> 2.
  • the diamines lead to a chain extension of the prepolymers, while the polyamine with the functionality> 2 additionally incorporates crosslinking points in the molecule. Since the reaction of the prepolymer with the components of component (F) takes place in an aqueous medium, the compounds of component (F) are characterized by a far higher reactivity towards isocyanate groups than water.
  • the amount of component (F) to be used depends on the unreacted isocyanate groups of the prepolymer which are still present.
  • Suitable diamines are, for example, 1,2-diaminoethane, 1,6-diaminohexane, piperazine, 2,5-dimethylpiperazine, l-amino-3-aminomethyl-3,5,5-trimethy! Cyclohexane, 4,4'-diaminodicylo-hexylmethane , 1, 4-diaminocyclohexane and / or 1, 2-propylenediamine. Hydrazine, amino acid hydrazides, bishydrazides and bis-semicarbazides are also suitable as chain extenders.
  • polyamines with a functionality of> 2 are diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, polyethyleneimines and melamine.
  • Polyurethane-polyurea dispersions which have the composition according to the invention and were produced by the processes described are very finely divided, stable in storage and have pH values in the range from 6 to 9.
  • the solids contents are between 20 and 60% by weight, in particular between 25 and 45% by weight.
  • the organic solvent content is at most 15% by weight.
  • the polyurethane polyurea dispersions according to the invention provide coatings with very good chemical and in particular very good ethanol resistance.
  • the new polyurethane polyurea dispersions can be used as paint binders for coating any substrates. These include organic and inorganic materials such as glass, wood, metals, plastics, leather and paper.
  • the polyurethane polyurea dispersions according to the invention can be used as the sole binder. However, there is the possibility of blending with other dispersions, such as polyvinyl acetate, polyethylene, polystyrene, polybutadiene, polyvinyl chloride, polyacrylate and copolymer plastic dispersions.
  • auxiliaries and additives customary in coating technology such as pigments, fillers, plasticizers, matting agents, coalescing agents, waxes, defoamers and wetting agents, can be incorporated into the dispersions according to the invention.
  • lacquers are applied using the usual methods of lacquer technology, for example by spraying, pouring, dipping or rolling.
  • NMP N-methylpyrrolidone
  • the batch is then cooled to room temperature, 3.7 g of triethylamine being added at about 45 ° C. to neutralize the dimethylolpropionic acid.
  • the prepolymer solution obtained is stirred vigorously at about 25 ° C dispersed in 250 g of water Finally, a mixture of 3.6 g of ethylenediamine and 4.1 g of diethylenetriamine dissolved in 25 g of water is added to the dispersion formed.
  • the dispersion obtained has a solids content of 34.7% by weight. and an NMP content of 14.5% by weight.
  • the pH is 7.6 and the run-out time (measured in the DIM-4 beaker) is 18 s
  • 9.7 g neopenyl glycol, 3.0 g t ⁇ methylolpropane, 11.5 g dimethylol propionic acid and 123.4 g 4.4 '-Diisocyanatd ⁇ cyclohexylmethan ( Desmodur W) weighed at room temperature and dissolved in 98.4 g of N-methylpyrrohdon (NMP). Then 0.23 g of dibutylzmndilaurate are added and the mixture is heated to 75 ° C.
  • NMP N-methylpyrrohdon
  • NMP N-methylpyrrolidone
  • dibutylzmndilaurate N-methylpyrrolidone dissolved 0.18 g of dibutylzmndilaurate are then added and the batch is heated to 65 ° C. and stirred at this temperature for 5 hours. The batch is then cooled to room temperature, 7.5 g of triethylamine being added at about 45 ° C. Neutralization of the dimethylolpropionic acid are added. The prepolymer solution obtained is stirred vigorously at about 25 ° C. in 290 g
  • Dispersed water Finally, a mixture of 3.6 g of ethylenediamine and 4.1 g of diethylenetriamine dissolved in 25 g of water egg is added to the dispersion formed.
  • the dispersion obtained has a solids content of 35% by weight and an NMP content of 14.5% by weight.
  • the pH is 7.2 and the run-out time (measured in a DIN 4 cup) is 20 s
  • NeoRez R-961 and NeoRez R-974 commercial products from Zeneca
  • U 710 and U 910 commercial products from Alberdingk Boley
  • NeoRez R-985 (commercial product from Zeneca), a polyurethane dispersion based on a polycarbonate diol, was included in the tests Checking the chemical resistance of the dispersions according to the invention and the comparative examples
  • the chemical resistance was checked on wood (ash).
  • the wooden surface was lightly pre-sanded with sandpaper and the sanding dust wiped off.
  • lifts with a wet film thickness of 120 ⁇ m were then drawn onto the wood test surface from the dispersions to be tested.
  • the wet films were then dried at 50 ° C. for 24 hours.
  • the lacquer surfaces were then sanded and the grinding dust removed.
  • a second lift with a thickness of 120 ⁇ m was then carried out. It was dried again at 50 ° C for 24 hours.
  • test areas were assessed after storage for 24 hours on the following grading scale
  • Dispersions have significantly better chemical resistance than the commercially available polyester-based polyurethane dispersions.
  • the resistance of the dispersion based on the polycarbonate diol is also exceeded

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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)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention concerne des dispersions à base d'urée de polyuréthane, obtenues par réaction de (A) entre 15 et 50 % en poids, de préférence entre 20 et 40 % en poids d'un polyol de polyester linéaire et/ou faiblement ramifié, d'un poids moléculaire compris entre 500 et 6000, (B) entre 2 et 10 % en poids, de préférence entre 3 et 7 % en poids d'un ou de plusieurs polyols d'un poids moléculaire ∫500, (C) entre 1 et 10 % en poids d'au moins un composé mono et/ou bifonctionnel qui contient en outre des groupes anioniques ou des groupes fonctionnels pouvant être transformés en groupes anioniques, (D) entre 0 et 15 % en poids d'un alcool mono ou bivalent hydrophile comportant des unités oxyde d'éthylène, de poids moléculaire compris entre 600 et 3000, (E) entre 30 et 70 % en poids, de préférence entre 40 et 60 % en poids d'un ou de plusieurs polyisocyanates, au moins 70 % en poids du constituant polyisocyanate consistant en un ou plusieurs diisocyanates cycloaliphatiques; puis par prolongation de la chaîne ou par réticulation du produit issu de (A) à (E) avec (F) entre 0,5 et 10 % en poids d'un mélange d'une ou de plusieurs diamines avec une polyamine de fonctionnalité ⊃2, au moins 20 % en poids du constituant (F) consistant en la polyamine de fonctionnalité ⊃2, la somme des constituants (A) à (F) formant toujours 100 %.
PCT/EP1997/003908 1996-08-01 1997-07-21 Dispersions aqueuses, leur preparation et leur utilisation comme liants pour peintures WO1998005696A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU39404/97A AU3940497A (en) 1996-08-01 1997-07-21 Aqueous dispersions, their preparation and use as paint binders

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1996130905 DE19630905A1 (de) 1996-08-01 1996-08-01 Wäßrige Dispersionen, ihre Herstellung und Verwendung als Lackbindemittel
DE19630905.0 1996-08-01

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WO1998005696A1 true WO1998005696A1 (fr) 1998-02-12

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Cited By (5)

* Cited by examiner, † Cited by third party
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US6177509B1 (en) 1998-09-23 2001-01-23 Bayer Ag Aqueous polymer dispersions neutralized with N,N-diisopropyl-N-ethylamine
EP1736246A1 (fr) * 2005-06-20 2006-12-27 E.I.Du pont de nemours and company Procédé de revêtement multicouches d'un substrat
US20120160437A1 (en) * 2010-12-22 2012-06-28 Bayer Materialscience Ag Process for the production of sized and/or wet-strength papers, paperboards and cardboards
CN106497018A (zh) * 2016-11-08 2017-03-15 株洲时代新材料科技股份有限公司 一种多组分聚氨酯填缝剂及其制备方法
CN115322530A (zh) * 2022-08-10 2022-11-11 江阴市龙山合成材料有限公司 一种无卤阻燃的增强型pbt及其加工工艺

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EP0982331B1 (fr) * 1998-08-28 2005-10-26 Council of Scientific and Industrial Research Un procédé amélioré pour la préparation des dispersions stables aqueuses d'uréthane
DE19904624C2 (de) * 1999-02-05 2002-02-07 Basf Coatings Ag Polyurethan und seine Verwendung in der wäßrigen Kunststofflackierung
DE10004723A1 (de) * 2000-02-03 2001-08-09 Bayer Ag Wässrige Sperrschicht auf Basis von Polyurethan-Disperionen
WO2000050482A1 (fr) 1999-02-25 2000-08-31 Bayer Aktiengesellschaft Couche barriere aqueuse a base de dispersions de polyurethanne
DE10152294A1 (de) 2001-10-26 2003-05-08 Solutia Austria Gmbh Werndorf Hochmolekulare Polyurethan-Dispersionen
AT411998B (de) * 2002-01-02 2004-08-26 Surface Specialties Austria Oberflächenschutz für lackierte flächen

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EP0242731A2 (fr) * 1986-04-22 1987-10-28 Bayer Ag Procédé pour la préparation de dispersions aqueuses de polyuréthane-polyurées et leur utilisation comme ou pour la préparation de masses de revêtement
DE4016713A1 (de) * 1990-05-24 1991-11-28 Bayer Ag Waessrige polymerdispersionen und deren verwendung als beschichtungsmittel fuer textile substrate und leder
EP0507173A2 (fr) * 1991-04-05 1992-10-07 Bayer Corporation Dispersions de polyuréthane-urée aqueuses à partir de bis-(4-isocyanatocyclohexyl)-méthane ayant un taux d'isomère trans, trans élevé et les revêtements ou les pellicules ainsi obtenus
EP0735069A1 (fr) * 1995-03-22 1996-10-02 Mitsubishi Chemical Corporation Procédé de préparation d'un revêtement aqueux de polyuréthane et couche obtenue à partir de celui-ci

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0242731A2 (fr) * 1986-04-22 1987-10-28 Bayer Ag Procédé pour la préparation de dispersions aqueuses de polyuréthane-polyurées et leur utilisation comme ou pour la préparation de masses de revêtement
DE4016713A1 (de) * 1990-05-24 1991-11-28 Bayer Ag Waessrige polymerdispersionen und deren verwendung als beschichtungsmittel fuer textile substrate und leder
EP0507173A2 (fr) * 1991-04-05 1992-10-07 Bayer Corporation Dispersions de polyuréthane-urée aqueuses à partir de bis-(4-isocyanatocyclohexyl)-méthane ayant un taux d'isomère trans, trans élevé et les revêtements ou les pellicules ainsi obtenus
EP0735069A1 (fr) * 1995-03-22 1996-10-02 Mitsubishi Chemical Corporation Procédé de préparation d'un revêtement aqueux de polyuréthane et couche obtenue à partir de celui-ci

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6177509B1 (en) 1998-09-23 2001-01-23 Bayer Ag Aqueous polymer dispersions neutralized with N,N-diisopropyl-N-ethylamine
EP1736246A1 (fr) * 2005-06-20 2006-12-27 E.I.Du pont de nemours and company Procédé de revêtement multicouches d'un substrat
US20120160437A1 (en) * 2010-12-22 2012-06-28 Bayer Materialscience Ag Process for the production of sized and/or wet-strength papers, paperboards and cardboards
US8647471B2 (en) * 2010-12-22 2014-02-11 Bayer Materialscience Llc Process for the production of sized and/or wet-strength papers, paperboards and cardboards
CN106497018A (zh) * 2016-11-08 2017-03-15 株洲时代新材料科技股份有限公司 一种多组分聚氨酯填缝剂及其制备方法
CN106497018B (zh) * 2016-11-08 2019-05-03 株洲时代新材料科技股份有限公司 一种多组分聚氨酯填缝剂及其制备方法
CN115322530A (zh) * 2022-08-10 2022-11-11 江阴市龙山合成材料有限公司 一种无卤阻燃的增强型pbt及其加工工艺

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AU3940497A (en) 1998-02-25

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