WO2008136732A1 - Polymère terminé par isocyanate et son utilisation dans une dispersion de polyuréthane durcissable par rayonnement - Google Patents

Polymère terminé par isocyanate et son utilisation dans une dispersion de polyuréthane durcissable par rayonnement Download PDF

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Publication number
WO2008136732A1
WO2008136732A1 PCT/SE2008/000305 SE2008000305W WO2008136732A1 WO 2008136732 A1 WO2008136732 A1 WO 2008136732A1 SE 2008000305 W SE2008000305 W SE 2008000305W WO 2008136732 A1 WO2008136732 A1 WO 2008136732A1
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WO
WIPO (PCT)
Prior art keywords
weight
terminated polymer
isocyanate terminated
polymer according
polyol
Prior art date
Application number
PCT/SE2008/000305
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English (en)
Inventor
Kent SÖRENSEN
Henrik Bernquist
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Perstorp Specialty Chemicals Ab
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Perstorp Specialty Chemicals Ab filed Critical Perstorp Specialty Chemicals Ab
Priority to EP08753933A priority Critical patent/EP2147033A4/fr
Publication of WO2008136732A1 publication Critical patent/WO2008136732A1/fr

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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
    • C08G18/65—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
    • 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
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/6705—Unsaturated polymers not provided for in the groups C08G18/671, C08G18/6795, C08G18/68 or C08G18/69
    • 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
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/675—Low-molecular-weight compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds

Definitions

  • the present invention refers to an isocyanate (NCO) terminated polymer obtained by co- polymerisation of at least one diol optionally in combination with at least one polyol (alcohol having three or more hydroxyl groups), at least one hydrophilic compound, at least one isocyanate and at least one polyol monoacrylate, monomethacrylate and/or monocrotonate.
  • NCO isocyanate
  • the present invention refers to the use of said polymer as pre-polymer in preparation of a radiation curable polyurethane dispersion.
  • a conventional, such as a non UV curable polyurethane dispersion (PUD) has in general good coating properties but deficient chemical and abrasion resistance due to the lack of crosslinking.
  • a crosslinkable polymer can be obtained by incorporation of unsaturated groups.
  • Systems that are 100% UV curable have a high degree of crosslinking that provides coatings with high hardness, high chemical resistance and high gloss. However, due to the high crosslinking density these systems have poorer flexibility, are tacky until they are cured and are not sprayable without using organic solvent and/or skin irritating low viscous monomers.
  • the two most common routs to obtain a UV curable PUD are either to make a physical blend of a conventional PUD and external acrylates or to end cap a NCO terminated pre-polymer with a monohydroxyfunctional acrylate, such as 2-hydroxyethyl acrylate or pentaerythritol triacrylate.
  • a monohydroxyfunctional acrylate such as 2-hydroxyethyl acrylate or pentaerythritol triacrylate.
  • acrylic groups are distributed along the polyurethane chain, providing a higher acrylate concentration and a more homogeneous crosslinking network resulting in improved properties suitable for coatings. These polyurethane dispersions form, when cured, coating films having substantial hardness with maintained flexibility.
  • an isocyanate (NCO) terminated polymer comprising units from at least one polyol monoacrylate, monomethacrylate and/or monocrotonate advantageously can be used in polyurethane dispersions providing similar excellent coating properties as for instance the polyurethane dispersions disclosed in WO 2006/089935, but with the benefit of a reduced number of process steps.
  • NCO isocyanate
  • a polyurethane dispersion prepared using the isocyanate terminated pre-polymer of the present invention only needs UV radiation, no heat, to cure.
  • isocyanate terminated polymer of the present invention is that it is aqueous dispersible without the addition of any second binder component.
  • Polyisocyanates like for example the one disclosed in the US patent 6162506 is not aqueous dispersible without the addition of latex.
  • the isocyanate terminated polymer of the present invention is obtainable by subjecting a) 10-90%, preferably 20-50% and most preferably 20-40%, by weight of at least one diol optionally in combination with at least one polyol, said diol and said optional polyol having a molecular weight of at most 5000 g/mol, b) 1-40%, preferably 3-15% and most preferably 4-10%, by weight of at least one hydrophilic compound, c) 20-60%, preferably 30-50% and most preferably 30-45%, by weight of at least one isocyanate, and d) 0.1-30%, preferably 1-20% and most preferably 5-15%, by weight of at least one polyol monoacrylate, monomethacrylate and/or monocrotonate, to co-polymerisation optionally in the presence of a catalyst, a solvent, a polymerisation inhibitor and/or other auxiliary components known in the art.
  • Said diol and said optional polyol are in preferred embodiments of the present invention selected from the group consisting of polyester diols and polyols, polyether diols and polyols and polycarbonate diols and polyols.
  • These diols and polyols, containing at least two reactive groups which enable them to react with isocyanates, preferably have an average molecular weight within the range of 100 and 5000 g/mol, and can be exemplified by poly(hexanediol adipate).
  • Said hydrophilic compound is preferably a polyol having an incorporated or pendant hydrophilic functionality, ionic or non-ionic, which is incorporated in the pre-polymer to make it self-dispersible in water.
  • the hydrophilic compound is most preferably a polyol, alkoxylated, such as ethoxylated, propoxylated and/or butoxylated, polyol and/or alkylated species there of and/or an amine comprising anionic salt groups, or acid which may be converted to such anionic salt groups, like carboxylate or sulphonate salt groups.
  • the hydrophilic compound can in specific preferred embodiments be exemplified by dimethylolpropionic acid, dimethylolbutyric acid, ⁇ , ⁇ -bis(hydroxymethyl)valeric acid, ⁇ , ⁇ - bis(hydroxy)propionic acid and/or 3,5-dihydroxybenzoic acid.
  • the most preferred isocyanate is a diisocyanate or a triisocyanate.
  • Suitable isocyanates are found hi the group consisting of for instance hexamethylene diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, tetramethylxylylene diisocyanate, 1,6-hexane diisocyanate, trimethylhexane diisocyanate, 1,12-dodecane diisocyanate, cyclohexane diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, bicyclohexylmethane diisocyanate, nonane triisocyanate, isophorone isocyanurate, 1,6-hexane diisocyanate isocyanurate, hydrogenated methylene diphenyl diisocyanate and methylene diphenyl diisocyanate.
  • Said polyol monoacrylate, monomethacrylate and/or monocrotonate is in the most preferred embodiments of the present invention a glycerol and/or a 2-alkyl-2-hydroxyalkyl-l,3- propanediol monoacrylate, monomethacrylate and/or monocrotonate in its cis or trans form.
  • Said glycerol and/or said 2-alkyl-2-hydroxyalkyl- 1,3 -propanediols include alkoxylated, such as ethoxylated, propoxylated and/or butoxylated, species thereof.
  • Preferred embodiments of said 2-alkyl-2-hydroxyalkyl-l,3-propanediols can be exemplified by trimethylolethane, trimethylolpropane and trimethylolbutane and/or said alkoxylated species thereof.
  • Said polyol monoacrylate, monomethacrylate and/or monocrotonate is hi its most preferred embodiments trimethylolpropane monoacrylate, monomethacrylate and/or monocrotonate.
  • Said monoacrylate, monomethacrylate and/or monocrotonate is suitably prepared by conventional and known in the art acrylation processes, such as transesterification and esterification in presence of a catalyst.
  • Catalysts which can be used to accelerate the reaction of the isocyanates are in embodiments of the present invention amines or organometallic compounds such as tin(II) or tin(III) octoate, diazadicyclo[2.2]octane or most preferably dibutyltin dilaurate.
  • the reaction is monitored by the consumption of isocyanate groups and is allowed to continue until a constant NCO value is obtained.
  • Suitable solvents are preferably found among glycol ethers, glycol ether esters, carboxylic acid esters, ketones, alkanols and aliphatic, cycloaliphatic, aromatic hydrocarbons, n-alkyl pyrrolidinones and/or alkylene carbonates.
  • a suitable solvent is for instance dipropylene glycol dimethyl ether or n-methyl pyrrolidinone.
  • a polymerisation inhibitor is, to prevent the acrylates from polymerisation at the elevated temperatures during the synthesis, suitably used.
  • Inhibitors can be exemplified by phenothiazine, 4-methoxyphenol or hydroquinone and derivatives thereof.
  • the present invention relates to the use of at least one polymer, according to the present invention, as pre-polymer in preparation of a radiation curable polyurethane dispersion (PUD).
  • PID radiation curable polyurethane dispersion
  • Said dispersion comprises a) 5-80%, preferably 35-45%, by weight of said polymer, b) 0.1-10%, preferably 0.5-3%, by weight of at least one neutralisation agent, and c) 20-90%, preferably 40-65%, by weight of water, and optionally d) 0.1-5%, preferably 0.5-2%, by weight of a chain extender, such as a diamine and/or a triamine.
  • a chain extender such as a diamine and/or a triamine.
  • Photochemically and/or thermally activating initiators may optionally be added and if desired UV absorbers, light stabilisers, pigments, fillers and/or other auxiliary additives.
  • Suitable neutralisation agent is added for neutralisation of the carboxylic or sulphonic acid groups to provide a stable salt.
  • Suitable neutralisation agents for converting acid groups into anionic salt groups before dispersion in water can be volatile organic bases and/or non-volatile bases.
  • Suitable organic bases can be selected from a group consisting of ammonia, trimethyl amine, triethyl amine, triisopropyl amine, and tributyl amine.
  • Suitable non-volatile inorganic bases are preferably bases comprising alkali metals such as lithium, sodium or potassium. These bases can be used in the form of inorganic or organic salts, preferably in the form of hydrides, hydroxides, carbonates or bicarbonates.
  • the water dispersible isocyanate terminated pre-polymer is then added to water, or water is added to the pre-polymer to form the dispersion.
  • a chosen part of the remaining isocyanates in the dispersed isocyanate terminated pre-polymer can be chain extended using a polyamine.
  • the chain extender is preferably a water soluble aliphatic, cycloaliphatic or aromatic polyamine with an average functionality between 2 and 4, most preferably 2 or 3, such as ethylene diamine, hexamethylene diamine, 1 ,4-cyclohexylene diamine, piperazine, N-methyl-propylene diamine, isophorone diamine and/or diethylene triamine.
  • the obtained aqueous radiation curable polyurethane dispersion may further comprise coalescent agents and/or reactive diluents such as ethylene glycol, propylene glycol, neopentyl glycol, trimethylolpropane, trimethylolbutane, glycerol, pentaerythritol, di- trimethylolpropane, di-trimethylolbutane, di-pentaerythritol, 2-butyl-2-ethyl- 1,3 -propanediol, 2-ethyl-2-methyl-l,3-propanediol and/or acrylated, methacrylated or crotonated derivatives.
  • coalescent agents and reactive diluents are alkoxylated and allylated species of above said polyhydric alcohols.
  • Said aqueous radiation curable polyurethane dispersion obtained is suitably used in coating compositions with high demands on hardness, abrasion and scratch resistance, flexibility and chemical resistance.
  • the dispersion may comprise additional components, such as photo initiators, pigments, dyes, defoamers, fillers and known in the art coating auxiliaries. Obtained coatings exhibit high hardness, scratch resistance, chemical resistance and a substantially reduced or even eliminated surface tack.
  • polyurethane dispersions comprising the polymer of the present invention, have good coating properties and good mechanical properties, especially good hardness. This is a major advantage compared to conventional UV curing polyurethane dispersions, which usually obtain satisfactorily properties only after UV curing.
  • Coatings comprising the inventive polymer exhibit even greater hardness and still good flexibility and excellent chemical resistance after radiation curing.
  • Polymers according to the present invention can suitably be used in coating of three dimensional objects wherein it is difficult to UV irradiate all surfaces, coatings applied in thick layers and in pigmented systems.
  • the acrylate groups along the polyurethane chain instead of using monofunctional acrylates such as 2-hydroxyethyl acrylate to end cap the polyurethane, higher molecular weight polymers and higher concentration of unsaturation are obtained.
  • the acrylate groups distributed along the polyurethane chain enables higher cross linking density.
  • the UV polyurethane dispersion containing the inventive polymer will have very good coating properties even when not UV cured.
  • Example 1 is a comparison example outside the scope of the invention wherein a conventional polyurethane dispersion is prepared.
  • Example 2 illustrates the invention and refers to a process wherein a UV curable polyurethane dispersion is prepared at a molar ratio polyol to hydrophilic compound to polyol monoacrylate of 1 : 1 : 1.
  • Example 3 illustrates the invention and refers to a process wherein a UV curable polyurethane dispersion is prepared at a molar ratio polyol to hydrophilic compound to polyol monoacrylate of 1 : 1 :2.
  • Example 4 refers to coating evaluations of the polyuretane dispersions obtained in Examples 1-3.
  • Step 1 Polymer Formulation
  • poly(hexanediol adipate) 45.5% by weight of poly(hexanediol adipate) was charged into a glass reactor equipped with stirrer, condenser, nitrogen inlet and thermometer and dried at 80 0 C for 30 min under vacuum. The temperature was then decreased to 50 0 C followed by addition of 6.1% by weight of dimethylolpropionic acid, 18.1% by weight of dipropylene glycol dimethyl ether and 0.045% by weight of dibutyltin dilaurate under stirring and while purging the reactor with dry nitrogen. 30.3% by weight of isophorone diisocyanate was slowly added, where after the temperature was increased to 75°C. The reaction was run until a constant NCO value was obtained, determined by standard NCO back titration method.
  • Step 1 39.8% by weight of the polymer obtained in Step 1 was charged into a reactor according to the first stage and the temperature was increased to 50 0 C followed by addition of 1.5% by weight of triethyl amine. After 5 min of mixing the agitation was increased from 120 to 300 rpm and 57.8% by weight of water was added without foaming. The heater was removed and after 5-10 min 1.0% by weight of ethylene diamine was added and the temperature of the dispersion was allowed to cool to room temperature with maintained stirring.
  • Step 1 Polymer Formulation
  • 35.0% by weight of poly(hexanediol adipate) was charged into a glass reactor equipped with stirrer, condenser, nitrogen inlet and thermometer and dried at 80 0 C for 30 min under vacuum. The temperature was then decreased to 50 0 C followed by addition of 4.7% by weight of dimethylolpropionic acid, 18.8% by weight of dipropylene glycol dimethyl ether, 0.035% by weight of dibutyltin dilaurate, 0.0033% by weight of phenothiazine and 6.6% by weight of trimethylol propane mono acrylate under stirring and while purging the reactor with dry nitrogen. 34.9% by weight of isophorone diisocyanate was slowly added, where after the temperature was increased to 75°C. The reaction was run until a constant NCO value was obtained.
  • Step 2 Neutralisation and Chain Extension of Polymer The procedure of Step 2 in Example 1 was repeated.
  • Step 1 Polymer Formulation
  • Step 2 Neutralisation and Chain Extension of Polymer The procedure of Step 2 in Example 1 was repeated.
  • Irgacure 500 (CIBA, Be) was added to the polyurethane dispersions obtained in Examples 1-3, which was then applied, using a K-bar wire applicator, to various substrates in coat thickness of approximately 100 ⁇ m. The water and solvent was removed from the coated substrates at a temperature of 80 °C during 30 min and finally the coatings made from the dispersions of Examples 2 and 3 were cured with a UV dose of 1000 mJ/cm 2 .
  • Hardness was determined by the K ⁇ nig pendulum hardness according to DIN EN ISO 1552.
  • the pendulum hardness is improved with increasing amounts of acrylates.
  • the pendulum hardness is substantially increased when UV cured. Despite the high hardness the flexibility is maintained in all coatings.
  • the chemical resistance is substantially improved compared to the conventional coating based on the dispersion of Example 1 with the UV cured coatings in example 2 and 3 which all show a great chemical resistance.
  • Table 2 also shows that the non UV cured coatings of Example 2 and 3 obtain better results than the conventional polyurethane dispersion from Example 1.

Abstract

La présente invention porte sur un polymère terminé par isocyanate que l'on peut obtenir en soumettant 10-90 % en poids d'au moins un diol facultativement en combinaison avec au moins un polyol, ledit diol et ledit polyol facultatif ayant une masse moléculaire d'au plus 5 000 g/mol, 1-40 % en poids d'au moins un composé hydrophile, 20-60 % en poids d'au moins un isocyanate et 0,1-30 % en poids d'au moins un polyol monoacrylate, monométhacrylate et/ou monocrotonate à une copolymérisation facultativement en présence d'un catalyseur, d'un solvant et/ou d'un inhibiteur de polymérisation. Dans un autre aspect, une dispersion de polyuréthane à durcissement par UV comprenant ledit polymère est décrite.
PCT/SE2008/000305 2007-05-04 2008-04-30 Polymère terminé par isocyanate et son utilisation dans une dispersion de polyuréthane durcissable par rayonnement WO2008136732A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP08753933A EP2147033A4 (fr) 2007-05-04 2008-04-30 Polymère terminé par isocyanate et son utilisation dans une dispersion de polyuréthane durcissable par rayonnement

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE0701095-2 2007-05-04
SE0701095A SE0701095L (sv) 2007-05-04 2007-05-04 Isocyanatterminerad polymer och dess användning i en strålningshärdande polyuretandispersion

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WO2008136732A1 true WO2008136732A1 (fr) 2008-11-13

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EP (1) EP2147033A4 (fr)
SE (1) SE0701095L (fr)
WO (1) WO2008136732A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2159265A1 (fr) * 1994-09-28 1996-03-29 Lukas Hausling Emulsions aqueuses de polyurethanne durcissables aux rayonnements
US5556912A (en) * 1993-12-23 1996-09-17 Herberts Gmbh Aqueous binder dispersion for physically drying coating compositions and use thereof
US6162506A (en) 1997-05-31 2000-12-19 Basf Coatings Ag Aqueous coating materials and methods of making and using same
US6583214B1 (en) * 1999-04-01 2003-06-24 Basf Coatings Ag Aqueous coating material that is cured thermally and/or by actinic radiation, and its use
US6747088B1 (en) 1999-09-30 2004-06-08 Basf Aktiengesellschaft Aqueous polyurethane dispersions which can be hardened with mit UV-radiation and thermally, and use thereof
WO2006089935A1 (fr) 2005-02-24 2006-08-31 Basf Aktiengesellschaft Dispersions de poluyrethanne aqueuses durcissables par rayonnement

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE528577C2 (sv) * 2005-03-23 2006-12-19 Perstorp Specialty Chem Ab Vattenburen polyuretandispersion samt användning därav

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5556912A (en) * 1993-12-23 1996-09-17 Herberts Gmbh Aqueous binder dispersion for physically drying coating compositions and use thereof
CA2159265A1 (fr) * 1994-09-28 1996-03-29 Lukas Hausling Emulsions aqueuses de polyurethanne durcissables aux rayonnements
US6162506A (en) 1997-05-31 2000-12-19 Basf Coatings Ag Aqueous coating materials and methods of making and using same
US6583214B1 (en) * 1999-04-01 2003-06-24 Basf Coatings Ag Aqueous coating material that is cured thermally and/or by actinic radiation, and its use
US6747088B1 (en) 1999-09-30 2004-06-08 Basf Aktiengesellschaft Aqueous polyurethane dispersions which can be hardened with mit UV-radiation and thermally, and use thereof
WO2006089935A1 (fr) 2005-02-24 2006-08-31 Basf Aktiengesellschaft Dispersions de poluyrethanne aqueuses durcissables par rayonnement

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP2147033A4 *

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Publication number Publication date
EP2147033A1 (fr) 2010-01-27
EP2147033A4 (fr) 2011-03-09
SE0701095L (sv) 2008-11-05

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