WO2007025670A1 - Wässrige 2k-pur systeme enthaltend hydroxy-funktionelle polydimethylsiloxane - Google Patents
Wässrige 2k-pur systeme enthaltend hydroxy-funktionelle polydimethylsiloxane Download PDFInfo
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- WO2007025670A1 WO2007025670A1 PCT/EP2006/008277 EP2006008277W WO2007025670A1 WO 2007025670 A1 WO2007025670 A1 WO 2007025670A1 EP 2006008277 W EP2006008277 W EP 2006008277W WO 2007025670 A1 WO2007025670 A1 WO 2007025670A1
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- PWFOLWIQYPIAGA-UHFFFAOYSA-N CC(C)(C)ON(C)C Chemical compound CC(C)(C)ON(C)C PWFOLWIQYPIAGA-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
-
- 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
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- 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
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4063—Mixtures of compounds of group C08G18/62 with other macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/61—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/703—Isocyanates or isothiocyanates transformed in a latent form by physical means
- C08G18/705—Dispersions of isocyanates or isothiocyanates in a liquid medium
- C08G18/706—Dispersions of isocyanates or isothiocyanates in a liquid medium the liquid medium being water
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
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- 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
Definitions
- the invention relates to aqueous 2K systems containing hydroxy-functional polydimethylsiloxanes.
- Two-component coating composition containing as binder a polyisocyanate component in combination with one opposite isocyanate groups.
- Reactive reactive component in particular a polyhydroxyl component, have long been known. They are suitable for the production of high-quality coatings that can be adjusted to hard, elastic, abrasion and solvent resistant.
- Aqueous two-component coating compositions have been known for years and are described, for example, in EP-A 0 358979.
- organofunctional PDMS types such as alkyleneamine or alkylene hydroxyl functional PDMS derivatives are used.
- organofunctional PDMS types such as alkyleneamine or alkylene hydroxyl functional PDMS derivatives are used.
- Such paint systems are e.g. in WO91 / 18954, EP-A 0 329 260 or US 4,774,278.
- the amine-functional PDMS types have the disadvantage that the pot life of polyurethane systems based thereon is extremely shortened due to the high tendency to urea formation.
- No. 6,475,568 describes the use of copolyols obtained by conversion of epoxy-functional PDMS oligomers and primary or secondary amines as an additive for cosmetic products or fabric softeners.
- WO 2004/022619 describes the use of chain extenders for polyurea systems which are obtained by the reaction of epoxy-functional PDMS with amines. The reaction of epoxy-functional PDMS with hydroxylamines to corresponding OH-functional compounds has not been described.
- the invention relates to aqueous compositions containing
- R is an aliphatic optionally branched Cp to C 2 o radical
- R 1 is an optionally branched hydroxyalkyl radical having 2 to 10 carbon atoms
- R 2 is either hydrogen or corresponds to the definition of the radical R 1
- the components A) and B) are preferably used in such a way that, based on the total amount of A) and B), from 0.01 to 20% by weight of component A) and from 80 to 99.99% by weight of component B), especially preferably 0.1 to 10 wt .-% A) and 90 to 99.90 wt .-% B) are present.
- the ratio of NCO groups to OH-functional compounds of components A) to C) is preferably 0.5: 1 to 5.0: 1, particularly preferably 0.8: 1 to 2: 1.
- the hydroxyl-containing polydimethylsiloxanes used in A) preferably have an average OH functionality of 1.9 to 6.
- Such hydroxyl-containing polydimethylsiloxanes to be used are obtainable by reacting corresponding epoxy-functional polydimethylsiloxanes with hydroxylamines preferably in a stoichiometric ratio of epoxy group to NH function.
- the epoxy-functional polydimethylsiloxanes used for this purpose preferably have 1 to 4 epoxy groups per molecule. Furthermore, they have number-average molecular weights of preferably 150 to 2800 g / mol, more preferably 250 to 2000 g / mol.
- Preferred epoxy-functional polydimethylsiloxanes are ⁇ , ⁇ -epoxy-dimethylsiloxanes corresponding to the formula (H) having the above molecular weights and an average of 2 epoxy functions per molecule.
- Such products are commercially available, for example, from GE Bayer Silicones, Leverkusen, Germany, Tego, Essen, Germany or Wacker, Kunststoff, Germany
- R is an optionally branched aliphatic Ci- to Cio radical
- n is an integer from 1 to 25.
- R 1 is an optionally branched hydroxyalkyl radical having 2 to 10 carbon atoms
- R 2 is either hydrogen or corresponds to the definition of the radical R 1 .
- Preferred hydroxylamines are ethanolamine, propanolamine, diethanolamine and dipropanolamine. Particularly preferred is diethanolamine.
- the epoxy-functional siloxane of the type mentioned above is optionally presented in a solvent and then reacted with the required amount of hydroxylamine or a mixture of several hydroxylamines.
- the reaction temperature is typically 20 to 150 0 C and is carried out until no more free epoxy groups are detectable.
- the hydroxyl-containing polydimethylsiloxanes of component A) which are obtainable as described above preferably have number-average molecular weights of from 250 to 2250 g / mol.
- Component B) comprises polymers containing hydroxyl groups and sulfonate and / or carboxylate groups.
- sulfonate and / or carboxylate groups encompasses both the deprotonated anionic sulfonate or carboxylate groups and the corresponding sulfonic acid and carboxylic acid functions.
- These polymers are more suitable olefinically unsaturated by free-radical polymerization
- Monomers obtainable and have a number average molecular weight M n of 500 to 50,000 g / mol, preferably 1,000 to 10,000 g / mol, a hydroxyl value of 16.5 to 264, preferably 33 to 165 mg KOH / g of solid resin, determined by gel permeation chromatography, an acid number (based on the non-neutralized sulfonic acid and / or carboxyl groups) of 0 to 150, preferably 0 to 100 mg KOH / g of solid resin and a content of sulfonate and / or
- Carboxylate groups from 5 to 417, preferably 24 to 278 milliequivalents per 100 g of solid.
- the polymers for anionic hydrophilization preferably have only carboxylate groups.
- the polymer resins B) are generally used in the preparation of the novel aqueous compositions in the form of from 10 to 50, preferably from 20 to 40,% by weight aqueous solutions and / or dispersions which generally have a viscosity of
- 10 to 10 5 preferably 100 to 10,000 mPa.s / 23 ° C and have pH values of 5 to 10, preferably 6 to 9.
- the aqueous systems containing the polymers are true dispersions, colloidally disperse or molecular disperse dispersions, but generally so-called "partial dispersions", ie to aqueous systems that are partly molecularly dispersed and partly colloidal.
- the preparation of the hydroxyl-containing polymers is carried out by per se known copolymerization of olefinically unsaturated monomers, as monomers both hydroxyl-containing monomers and acid group-containing monomers are generally copolymerized together with other monomers, after which the present acid groups are at least partially neutralized.
- the "acidic" comonomers come in amounts of 1 to 30, preferably 5 to
- Suitable "acidic" comonomers are in principle all olefinically unsaturated, polymerizable compounds which have at least one carboxyl and / or sulfonic acid group such as, for example, olefinically unsaturated mono- or dicarboxylic acids in the molecular weight range from 72 to 207 g / mol such as acrylic acid, methacrylic acid, maleic acid, itaconic acid or Sulfonic acid groups containing olefinically unsaturated compounds such as 2-acrylamido-2-methylpropanesulfonic acid or any mixtures of such olefinically unsaturated acids.
- carboxyl and / or sulfonic acid group such as, for example, olefinically unsaturated mono- or dicarboxylic acids in the molecular weight range from 72 to 207 g / mol such as acrylic acid, methacrylic acid, maleic acid, itaconic acid or Sulfonic acid groups containing ole
- the monomers having hydroxyl groups are used in amounts such that the abovementioned hydroxyl numbers of the polymers result, which, moreover, generally correspond to a hydroxyl group content of the polymers of from 0.5 to 8, preferably from 1 to 5,% by weight.
- the hydroxy-functional comonomers are used in amounts of 3 to 75, preferably 6 to 47 wt .-%, based on the total weight of the monomers used.
- the amount of hydroxy-functional monomers is chosen so that copolymers are formed which have at least two hydroxyl groups per molecule on average.
- Preferred hydroxyl-containing monomers are hydroxyalkyl esters of acrylic acid or methacrylic acid having preferably 2 to 4 carbon atoms in the alkyl radical such as 2-hydroxyethyl acrylate or methacrylate, 2- or 3-hydroxypropyl acrylate or methacrylate, and the isomeric hydroxybutyl acrylates or methacrylates or any mixtures of such monomers.
- the third group of olefinically unsaturated monomers which are generally used in the preparation of the copolymers are those olefinically unsaturated compounds which have neither acidic groups nor hydroxyl groups. These include, for example, esters of acrylic acid or of methacrylic acid having 1 to 18, preferably 1 to 8, carbon atoms in the alcohol radical such as methyl acrylate, ethyl acrylate, isopropyl acrylate, n-propyl acrylate, n-butyl acrylate, 2-ethylhexyl acrylate, n-stearyl acrylate, the methacrylates corresponding to these acrylates , Styrene, alkyl-substituted styrenes, acrylonitrile, methacrylonitrile, vinyl acetate or vinyl stearate or any mixtures of such monomers. Also
- Epoxide group-containing comonomers such as e.g. Glycidyl acrylate or methacrylate or monomers such as N-methoxymethylacrylamide or -methacrylamide can also be used in small amounts.
- the monomers of the latter third group without acid and hydroxyl groups are generally in amounts of up to 90 wt .-%, preferably 40 to 80 wt .-%, based on the
- the preparation of the polymers can be carried out by polymerization by conventional methods.
- the preparation of the polymers is preferably carried out in organic solution. Possible are continuous or discontinuous polymerization processes. Of the batch processes, the batch process and the feed process should be mentioned, the latter being preferred.
- the solvent is introduced alone or with a part of the monomer mixture, heated to the polymerization temperature, the polymerization in the case of a monomer masterbatch started radically and the remaining monomer mixture together with an initiator mixture in the course of 1 to 10 hours, preferably 3 to 6 hours, added.
- it is subsequently subsequently activated to carry out the polymerization to a conversion of at least 99%.
- suitable solvents are aromatics, such as benzene, toluene, xylene, chlorobenzene, esters, such as ethyl acetate, butyl acetate, methyl glycol acetate, ethyl glycol acetate, methoxypropyl acetate, Ethers such as butyl glycol, tetrahydrofuran, dioxane, ethyl glycol ethers, ketones such as acetone, methyl ethyl ketone, halogenated solvents such as methylene chloride or trichloromonofluoroethane into consideration.
- aromatics such as benzene, toluene, xylene, chlorobenzene
- esters such as ethyl acetate, butyl acetate, methyl glycol acetate, ethyl glycol acetate, methoxypropyl acetate
- Ethers such as butyl
- the initiated by free radical polymerization can be triggered by initiators whose half-lives of the radical decomposition at 80 to 180 0 C between 0.01 and 400 min. lie.
- the copolymerization reaction takes place in the temperature range mentioned, preferably between 100 and 16O 0 C, under a pressure of 10 3 to 2 x 10 4 mbar, wherein the exact polymerization temperature depends on the type of initiator.
- the initiators are used in amounts of 0.05 to 6 wt .-%, based on the total amount of monomers.
- Suitable initiators are e.g. aliphatic azo compounds such as azoisobutyronitrile and
- Peroxides such. As dibenzoyl peroxide, t-butyl perpivalate, t-butyl-per-2-ethylhexanoate, t-butyl perbenzoate, t-butyl hydroperoxide, di-t-butyl peroxide, cumene hydroperoxide and dicyclohexyl and Dibenzylperoxydicarbonat.
- Conventional regulators can be used to control the molecular weight of the polymers, such as n-dodecyl mercaptan, diisopropylxanthogen disulphide, di (methylene trimethylolpropane) xanthogen disulphide and thioglycol. They are added in amounts of at most 3% by weight, based on the monomer mixture.
- the copolymers are converted into an aqueous solution or dispersion.
- the organic polymer solution is introduced into a usually preheated water phase and at the same time the organic solvent is removed by distillation, generally under application of a vacuum.
- a neutralizing agent such as inorganic bases, ammonia or amines
- inorganic bases for example, sodium hydroxide, potassium hydroxide, as amines in addition to ammonia trimethylamine, triethylamine, dimethylethanolamine can be used.
- the neutralizing agents can be used both in the stoichiometric lower and in excess, with the abovementioned contents of sulfonate and / or carboxylate groups, in particular of carboxylate groups, resulting in the abovementioned acid numbers.
- the acid number will then be zero, while the content of sulfonate and / or carboxylate groups will correspond to the original content of sulfonic acid groups or carboxyl groups.
- the contents of sulfonate and / or carboxylate groups correspond to the amount of neutralizing agent used.
- the resulting aqueous solutions or dispersions have the abovementioned concentrations and viscosities and generally have a residual solvent content of less than 5% by weight, preferably less than 2% by weight.
- the virtually complete removal of higher than water-boiling solvents is possible by azeotropic distillation.
- Suitable polyisocyanates of component C) are organic polyisocyanates having an average NCO functionality of at least 2 and a molecular weight of at least 140 g / mol. Especially suitable are (i) unmodified organic polyisocyanates of the number average molecular weight range from 140 to 300 g / mol, (ii) coating polyisocyanates having a number average molecular weight of from 300 to 1000 g / mol and (iii) urethane group-containing NCO-
- polyisocyanates of group (i) are 1,4-diisocyanatobutane, 1,6-diisocyanatohexane (HDI), 1,5-diisocyanato-2,2-dimethylpentane, 2,2,4- and 2,4,4- Trimethyl-l, 6-diisocyanatohexane, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (IPDI), 1-isocyanato-1-methyl-4- (3) -isocyanatocyclohexane, bis ( 4-isocyanatocyclohexyl) methane, 1, 10-diisocyanatodecane, 1,12-diisocyanato-dodecane, cyclohexane-1,3- and -1,4-diisocyanate, xylylene diisocyanate isomers, triisocyanatononane (TIN), 2,4-diiso
- Polyisocyanates of group (ii) are the conventional lacquer polyisocyanates.
- lacquer polyisocyanates is to be understood as meaning compounds or mixtures of compounds which are obtained by per se known oligomerization reaction of simple diisocyanates of the type mentioned under (i) by way of example.
- Suitable oligomerization reactions are e.g. carbodiimidization, dimerization, trimerization, biuretization, urea formation, urethanization, allophanatization and / or cyclization to form oxadiazine structures. Often, in "oligomerization", several of the reactions mentioned occur simultaneously or in succession.
- the "paint polyisocyanates” (ii) are preferably biuret polyisocyanates, isocyanurate group-containing polyisocyanates, isocyanurate and uretdione groups Polyisocyanate mixtures, urethane and / or allophanate group-containing polyisocyanates or isocyanurate and allophanate group-containing polyisocyanate mixtures based on simple diisocyanates.
- Polyisocyanates of group (iii) are the per se known isocyanate prepolymers based on simple diisocyanates of the type exemplified above and / or based on lacquer polyisocyanates (ii) on the one hand and organic polyhydroxy compounds of over 300 g / mol lying number average molecular weight on the other hand.
- urethane-containing lacquer polyisocyanates of group (ii) are derivatives of low molecular weight polyols of the number average molecular weight range from 62 to 300 g / mol
- suitable polyols are, for example, ethylene glycol, propylene glycol, trimethylolpropane, glycerol or mixtures of these alcohols are used to prepare the NCO -Prepolymeren of group (iii) polyhydroxyl compounds having number average molecular weights of about 300 g / mol, preferably above 500 g / mol, particularly preferably from 500 to 8000 g / mol used.
- Such polyhydroxyl compounds are, in particular, those which have 2 to 6, preferably 2 to 3, hydroxyl groups per molecule and are selected from the group consisting of ether, ester, thioether, carbonate and polyacrylate polyols and mixtures of such polyols.
- the stated higher molecular weight polyols can also be used in mixtures with the mentioned low molecular weight polyols, so that directly mixtures of low molecular weight urethane-containing lacquer polyisocyanates (ii) and higher molecular weight NCO prepolymers (iii) result, which are also suitable as the starting component (C) according to the invention.
- Hydrophilization of the polyisocyanates is e.g. by reaction with substancial amounts of monohydric, hydrophilic polyether alcohols possible.
- the preparation of such hydrophilicized polyisocyanates is described for example in EP-A 0 540 985, page 3, Z 55 - page 4 Z.5.
- Also suitable are the polyisocyanates containing allophanate groups described in EP-A-959087, p. 3 Z. 39-51, which are low in monomer by reaction
- Polyisocyanates are prepared with Polyethylenoxidpolyetheralkoholen under allophanatization conditions. Also the water-dispersible polyisocyanate mixtures based on triisocyanatononane described in DE-A 100 078 21, p. 2 Z. 66 - p. 3 Z.5, are suitable, as well as with ionic groups (sulfonate, phosphonate) hydrophilized polyisocyanates, as they are eg in DE 10024624, p. 3 Z. 13 - 33 are described. Likewise possible is the
- Preferred hydrophilic polyisocyanates C) are polyisocyanates containing sulfonate groups.
- polystyrene resin preferably contain on average 5 to 35 ethylene oxide units.
- the sulfonate groups preferably have as counterion an ammonium ion formed from tertiary amines by protonation.
- the ratio of the sum of sulfonic acid groups and sulfonate groups to the sum of tertiary amine and the protonated ammonium ion derived therefrom is typically 0.2 to 2.0.
- tertiary amines examples include monoamines, such as trimethylamine, triethylamine, tripropylamine,
- Tributylamine dimethylcyclohexylamine, N-methylmorpholine, N-ethylmorpholine, N-methylpiperidine, N-ethylpiperidine, or tertiary diamines, such as 1,3-bis (dimethylamino) -propane, l, 4-bis (dimethylamino) butane or N, N'-dimethylpiperazine.
- suitable, but less preferred, neutralization amines are tertiary amines bearing isocyanate-reactive groups, for example alkanolamines, for example dimethylethanolamine, methyldiethanolamine or triethanolamine. Preference is given to dimethylcyclohexylamine.
- polyisocyanates of the abovementioned type with blocked NCO groups can also be used in C).
- the abovementioned polyisocyanates are used, wherein a blocking is dispensed with.
- Preferred polyisocyanates used in C) are the above-described hydrophilicized polyisocyanates.
- the polyisocyanates may be used in admixture with small amounts of inert solvents to lower the viscosity to a value within said ranges.
- the amount of such solvents is maximally dimensioned such that a maximum of 20% by weight is contained in the final coating compositions according to the invention.
- Solvent based on the amount of water is present, wherein the solvent optionally present in the polymer dispersions or solutions is also included in the calculation.
- Solvents which are suitable as additives for the polyisocyanates are, for example, aromatic hydrocarbons such as, for example, "solvent naphtha” or also solvents of the type already mentioned above by way of example.
- the invention also provides a process for producing such a varnish, in which the polyisocyanate component C) is emulsified in an aqueous solution or dispersion of components A) and B), the proportions of components A) to C) being such that an NCO / OH equivalent ratio of 0.5: 1 to 5: 1, preferably 0.8: 1 to 2: 1 results.
- the polymer component A Before the addition of the polyisocyanate component C), the polymer component A), i. of the
- Dispersion or solution of the polymers the usual auxiliaries and additives paint technology are incorporated. These include internal release agents, fillers, dyes, pigments, flame retardants, hydrolysis protectants, microbicides, flow control agents, solvents, antioxidants, defoaming agents, dispersing agents for pigment distribution and the like.
- the paints according to the invention are suitable for practically all fields of use in which today solvent-based, solvent-free or other aqueous paint and paint systems with an increased property profile are used, eg coating of virtually all mineral building material surfaces such as lime and / or cement-bound plasters, Plaster-containing surfaces, fiber-cement building materials ⁇ Concrete; Lacquering and sealing of wood and wood-based materials such as chipboard, wood fiber boards and paper; Painting of metallic surfaces; Painting asphalt or bituminous road surfaces; Painting and sealing of various plastic surfaces.
- mineral building material surfaces such as lime and / or cement-bound plasters, Plaster-containing surfaces, fiber-cement building materials ⁇ Concrete
- Lacquering and sealing of wood and wood-based materials such as chipboard, wood fiber boards and paper
- Painting of metallic surfaces Painting asphalt or bituminous road surfaces
- Painting and sealing of various plastic surfaces eg coating of virtually all mineral building material surfaces such as lime and / or cement-bound plasters, Plaster-containing surfaces, fiber-cement building materials ⁇ Concrete
- the dynamic viscosities were determined at 23 ° C using a rotational viscometer (Viscotester ® 550, Thermo Haake GmbH, D-76227 Düsseldorf) was determined.
- the OH number was determined according to DIN 53240 T.2
- the epoxide group content was determined according to DIN 16945, wherein in the context of the present invention the epoxide group content was based on a molar mass of 42 g / mol.
- the gloss measurement was carried out in accordance with DIN 67530.
- the pendulum hardness according to König was determined according to DIN 53157 after 7 days' storage at room temperature.
- the easy-to-clean properties were determined so that a Lumocolor Permanent Marker 350 (Staedler, Nuremberg, DE) was applied in red for 1 minute was allowed to act. It was then attempted to remove the mark with a dry and with a paper towel moistened in ethanol.
- a Lumocolor Permanent Marker 350 Staedler, Nuremberg, DE
- Surfynol 104 BC (50% in butane glycol): 2,4,7,9-tetramethyl-5-decyne-4,7-diol, Lanxess, Leverkusen, DE
- Borchigel PW 25 (25% in propane glycol / water): nonionic polyurethane-based thickener, Bayer MaterialScience AG, Leverkusen, DE
- Baysilone VP AI 3468 (10% in butane glycol): Surface additive Polyetherpolysiloxane, Borchers GmbH, Langenfeld DE
- Solvent naphtha 100 Aromatic solvent Preparation of Polyol I:
- Polyol II water-dilutable OH-functional polyacrylate dispersion ,. 45% strength by weight in water / solvent naphtha 100 / Dowanol PnB, neutralized with dimethylethanolamine / triethanolamine, OH content of 3.9%, OH number 128 mg KOH / g and a viscosity of 2000 mPa.s; Bayhydrol XP 2470, Bayer Material Science AG, Leverkusen, DE
- Polyisocyanate hydrophilic, aliphatic polyisocyanate based on 1, 6-hexamethylene diisocyanate, having an NCO content of 20.6% and a viscosity at 23 0 C of 5400 mPa.s; Bayhydur XP 2487/1, Bayer Material Science AG, Leverkusen, DE
- the components were mixed according to the following table with conventional lacquer additives, catalysts and polyisocyanates, with stirring, then applied with a 50 micron doctor blade on glass and cured 60 min at 100 0 C.
- Example 1 results in clear films with a smooth surface and good easy-to-clean properties.
- Example 2 without silicone component provides blunted films Surface and compared to Example 1 worse easy-to-clean properties.
- Examples 3 to 6 have worse easy-to-clean properties than Example 1.
- the films of Examples 3 and 4 have an oily surface, indicating that the silicone diol was not incorporated into the polyurethane matrix.
- Comparative Examples 5 and 6 have a blunt surface.
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Dispersion Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
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- Silicon Polymers (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE502006002461T DE502006002461D1 (de) | 2005-09-03 | 2006-08-23 | Wässrige 2k-pur systeme enthaltend hydroxy-funktionelle polydimethylsiloxane |
| JP2008528388A JP5210159B2 (ja) | 2005-09-03 | 2006-08-23 | ヒドロキシ官能性ポリジメチルシロキサンを含有する水性2k−pur系 |
| CN2006800321896A CN101253211B (zh) | 2005-09-03 | 2006-08-23 | 含羟基官能聚二甲基硅氧烷的水性双组分聚氨酯体系 |
| PL06763033T PL1924624T3 (pl) | 2005-09-03 | 2006-08-23 | Wodne dwuskładnikowe układy poliuretanowe zawierające polidimetylosiloksany z funkcją hydroksylową |
| EP06763033A EP1924624B1 (de) | 2005-09-03 | 2006-08-23 | Wässrige 2k-pur systeme enthaltend hydroxy-funktionelle polydimethylsiloxane |
| CA002621000A CA2621000A1 (en) | 2005-09-03 | 2006-08-23 | Aqueous two-component polyurethane systems containing hydroxy-functional polydimethylsiloxanes |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005041951A DE102005041951A1 (de) | 2005-09-03 | 2005-09-03 | Wässrige 2K-PUR Systeme enthaltend hydroxy-funktionelle Polydimethylsiloxane |
| DE102005041951.8 | 2005-09-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2007025670A1 true WO2007025670A1 (de) | 2007-03-08 |
Family
ID=37433782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| PCT/EP2006/008277 Ceased WO2007025670A1 (de) | 2005-09-03 | 2006-08-23 | Wässrige 2k-pur systeme enthaltend hydroxy-funktionelle polydimethylsiloxane |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20070055016A1 (enExample) |
| EP (1) | EP1924624B1 (enExample) |
| JP (1) | JP5210159B2 (enExample) |
| CN (1) | CN101253211B (enExample) |
| AT (1) | ATE418574T1 (enExample) |
| CA (1) | CA2621000A1 (enExample) |
| DE (2) | DE102005041951A1 (enExample) |
| ES (1) | ES2318768T3 (enExample) |
| PL (1) | PL1924624T3 (enExample) |
| WO (1) | WO2007025670A1 (enExample) |
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| WO2009059694A1 (de) * | 2007-11-08 | 2009-05-14 | Bayer Materialscience Ag | Polysiloxanmodifizierte polyisocyanate |
| EP2072583A2 (de) | 2007-12-19 | 2009-06-24 | Bayer MaterialScience AG | Silan-modifizierte Bindemitteldispersionen |
| EP2072553A2 (de) | 2007-12-19 | 2009-06-24 | Bayer MaterialScience AG | Siloxanhaltige Bindemitteldispersionen |
| CN102926208A (zh) * | 2012-10-16 | 2013-02-13 | 淮安凯悦科技开发有限公司 | 肤感的聚氨酯树脂人造革表面处理剂 |
| CN108276548A (zh) * | 2018-01-22 | 2018-07-13 | 南京理工大学 | 羟烃基封端聚二甲基硅氧烷改性水性聚氨酯复合材料的制备方法 |
| CN109251718A (zh) * | 2018-09-03 | 2019-01-22 | 东莞市阿普帮新材料科技有限公司 | 一种绝缘保护用紫外光固化胶、制备方法及其应用 |
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| JP2008543602A (ja) | 2005-05-09 | 2008-12-04 | エヌディーエスユー リサーチ ファウンデーション | ポリアミン架橋されたポリシロキサンを含有する防汚物質 |
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| US8709394B2 (en) | 2007-09-28 | 2014-04-29 | Ndsu Research Foundation | Antimicrobial polysiloxane materials containing metal species |
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| DE102015209627A1 (de) * | 2015-05-26 | 2016-12-01 | Rudolf Gmbh | Polyurethan-Organopolysiloxane |
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| CN110408321B (zh) * | 2018-04-26 | 2021-04-02 | 北京百耐尔防水工程有限公司 | 喷涂速凝橡胶沥青阻燃型防水涂料及其制备方法 |
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- 2006-08-23 ES ES06763033T patent/ES2318768T3/es active Active
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Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011503267A (ja) * | 2007-11-08 | 2011-01-27 | バイエル・マテリアルサイエンス・アクチェンゲゼルシャフト | ポリシロキサン変性ポリイソシアネート |
| WO2009059694A1 (de) * | 2007-11-08 | 2009-05-14 | Bayer Materialscience Ag | Polysiloxanmodifizierte polyisocyanate |
| WO2009059695A1 (de) * | 2007-11-08 | 2009-05-14 | Bayer Materialscience Ag | Nanopartikelmodifizierte polyisocyanate |
| US8278399B2 (en) | 2007-11-08 | 2012-10-02 | Bayer Materialscience Ag | Polysiloxane-modified polyisocyanates, processes for preparing the same, and polyurethanes containing the same |
| EP2058349A1 (de) * | 2007-11-08 | 2009-05-13 | Bayer MaterialScience AG | Nanopartikelmodifizierte Polyisocyanate |
| EP2072553A2 (de) | 2007-12-19 | 2009-06-24 | Bayer MaterialScience AG | Siloxanhaltige Bindemitteldispersionen |
| DE102007061875A1 (de) | 2007-12-19 | 2009-06-25 | Bayer Materialscience Ag | Siloxanhaltige Bindemitteldispersionen |
| JP2009173886A (ja) * | 2007-12-19 | 2009-08-06 | Bayer Materialscience Ag | シロキサン含有バインダー分散体 |
| DE102007061871A1 (de) | 2007-12-19 | 2009-06-25 | Bayer Materialscience Ag | Silan-modifizierte Bindemitteldispersion |
| EP2072583A2 (de) | 2007-12-19 | 2009-06-24 | Bayer MaterialScience AG | Silan-modifizierte Bindemitteldispersionen |
| US8299168B2 (en) | 2007-12-19 | 2012-10-30 | Bayer Materialscience Ag | Siloxane-containing binder dispersions |
| EP2072583A3 (de) * | 2007-12-19 | 2012-11-07 | Bayer MaterialScience AG | Silan-modifizierte Bindemitteldispersionen |
| US8802775B2 (en) | 2007-12-19 | 2014-08-12 | Bayer Materialscience Ag | Silane-modified binder dispersions |
| CN102926208A (zh) * | 2012-10-16 | 2013-02-13 | 淮安凯悦科技开发有限公司 | 肤感的聚氨酯树脂人造革表面处理剂 |
| CN108276548A (zh) * | 2018-01-22 | 2018-07-13 | 南京理工大学 | 羟烃基封端聚二甲基硅氧烷改性水性聚氨酯复合材料的制备方法 |
| CN109251718A (zh) * | 2018-09-03 | 2019-01-22 | 东莞市阿普帮新材料科技有限公司 | 一种绝缘保护用紫外光固化胶、制备方法及其应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2009507089A (ja) | 2009-02-19 |
| ATE418574T1 (de) | 2009-01-15 |
| US20070055016A1 (en) | 2007-03-08 |
| CN101253211A (zh) | 2008-08-27 |
| DE102005041951A1 (de) | 2007-03-08 |
| CN101253211B (zh) | 2011-09-07 |
| ES2318768T3 (es) | 2009-05-01 |
| DE502006002461D1 (de) | 2009-02-05 |
| EP1924624A1 (de) | 2008-05-28 |
| EP1924624B1 (de) | 2008-12-24 |
| PL1924624T3 (pl) | 2009-06-30 |
| CA2621000A1 (en) | 2007-03-08 |
| JP5210159B2 (ja) | 2013-06-12 |
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