WO2010020678A1 - Composition de revêtement résistante à l’eau et durcissant à l’humidité qui contient un polymère ayant des groupes silyle réactifs - Google Patents

Composition de revêtement résistante à l’eau et durcissant à l’humidité qui contient un polymère ayant des groupes silyle réactifs Download PDF

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WO2010020678A1
WO2010020678A1 PCT/EP2009/060799 EP2009060799W WO2010020678A1 WO 2010020678 A1 WO2010020678 A1 WO 2010020678A1 EP 2009060799 W EP2009060799 W EP 2009060799W WO 2010020678 A1 WO2010020678 A1 WO 2010020678A1
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weight
moisture
acid
composition according
curing composition
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PCT/EP2009/060799
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German (de)
English (en)
Inventor
Thomas Plantenberg
Klaus Helpenstein
Ralf Dunekake
Hartmut Urbath
Martin Theinert
Johann Klein
Manfred Grasse
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Henkel Ag & Co. Kgaa
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Publication of WO2010020678A1 publication Critical patent/WO2010020678A1/fr

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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
    • 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
    • C08G18/71—Monoisocyanates or monoisothiocyanates
    • C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
    • 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
    • C08G18/48—Polyethers
    • C08G18/4825—Polyethers containing two hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—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
    • C08G2190/00—Compositions for sealing or packing joints
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
    • C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
    • C08L2666/20—Macromolecular compounds having nitrogen in the main chain according to C08L75/00 - C08L79/00; Derivatives thereof

Definitions

  • the invention relates to water-resistant compositions based on silane-terminated polymers and their use as coating compositions, adhesives, sealants or for the sealing of structures.
  • Structures must be insulated against moisture or water penetration. This is particularly evident in roofs of buildings, but the same applies to civil engineering foundations and bridges and road construction. As a rule, these structures have components made from mineral, metallic or organic building materials, which are separated by joints or may crack during their lifetime. These joints or cracks of these components must be sealed either during the manufacture of the structure or during later repairs or renovations against the ingress of water, dirt or wind. For many years permanently plastic or viscoelastic coatings z. B. applied to flat roofs or connection joints in the establishment or required repair work.
  • bituminous sheets have been used.
  • this technique is rarely used today because sealing at corners, edges and passages is not easy and, despite careful work, leakages occur at these locations.
  • aqueous polymer dispersions or emulsions have been used, which are applied by brushing or spraying.
  • these sealing materials dry sufficiently quickly only at ambient temperatures greater than 15 ° C. At drying temperatures On the other hand, above 20 ° C., water is easily trapped, which can lead to blistering and leaks.
  • the stability of the aqueous coating compositions is poor, which is why it is necessary to apply several coatings one above the other in order to achieve sufficient layer thicknesses and thus adequate protection against penetrating moisture.
  • a moisture-curing liquid sealant is sprayed in a layer thickness of about 0.5 to 3 mm according to the teaching of EP185214 A1, which as binder a polyurethane prepolymer with isocyanate or capped isocyanate end groups, as a hardener an enamine or dienamine and plasticizers, fillers, fibers and optionally a solvent.
  • the viscosity of the sealant is about 5,000 to 25,000 mPa.s.
  • EP494457 A1 describes polyurethane reactive compositions comprising an NCO prepolymer based on diphenylmethane diisocyanate and an aliphatic polyether, a capped diamine as curing agent and at least one aromatic or aliphatic or mixed aliphatic / aromatic hydrocarbon having at least 18 carbon atoms and a zeolite of about 4 ⁇ .
  • These reactive compositions should be able to be used as coating or sealing agents, especially where wet substrates or underwater must be used.
  • DE19849817 A1 discloses alkoxysilane-terminated polyurethane prepolymers based on special, very high molecular weight polyurethane prepolymers, a process for their preparation and their use as binders for low-modulus sealants.
  • the crosslinked polymers should be characterized by excellent extensibility and low modulus at the same time.
  • products based on the preferred diol component to be used Polyoxypropylenglycole with low Automatunsuschickistsgrad proposed because they are characterized by low Moduli, excellent mechanical properties and low surface tackiness. Applications as a coating material are not disclosed.
  • WO2007 / 0933822 A1 aims to avoid this problem and proposes coating compositions which are distinguished by a viscosity-controlled composition of at least two methoxy-alkyl-silane-terminated polyoxypropylene types.
  • the coating compositions are suitable for sealing building structures or flat roofs.
  • the material should have such a thixotropy that it can be applied both in thick vertical layers (eg with the trowel) and as a paint (with brush or roller).
  • the thixotropy should be so pronounced that thicker layers in the vertical with a job are possible without slipping off.
  • the surface should still run with brush application so that a smooth surface is created.
  • the object of the present invention is therefore to provide moisture-curing waterproof coatings with the aforementioned special rheological properties.
  • compositions may also comprise at least one plasticizer or a mixture of plasticizers and / or at least one low molecular weight organofunctional silane.
  • the preferred rheological properties are determined by means of oscillation measurement at 25 ° C. and 0.1 % Deformation determined.
  • the quotient of the complex viscosities ( ⁇ * ) of the composition at 10 rad / s and 500 rad / s is determined, which is preferably between greater than 5 and 50, preferably between 10 and 30.
  • a measuring device is an oscillation rheometer ARES from the company TA Instruments, which is used for the determination of the mentioned parameters.
  • the determination of the rheological parameter ( ⁇ * ) by means of a frequency sweep on the above-mentioned device with a plate / plate measuring system.
  • the software-controlled calibration of the device takes place before the measurement by entering the respective measuring geometry and starting the automatic self-calibration.
  • the measurement was carried out by recording the test substance to be measured between 2 parallel plates (diameter: 25 mm, measuring gap: 1 mm, total deformation: 0.1%).
  • the frequency-dependent complex viscosities ( ⁇ * ) were measured at angular velocities (frequencies) of 10 rad / s and 500 rad / s and the quotient of the values for 10 rad / s and 500 rad / s was formed.
  • This quotient Q of the complex viscosities ( ⁇ * ) at 10 rad / s and 500 rad / s [Q ⁇ * (10 rad / s) / ⁇ * (500 rad / s)] is a measure of the thixotropy of the measured compositions ,
  • the delay (equilibration / resting phase) before each measurement is 60s.
  • the measuring method described is known to the person skilled in the art and standardized in DIN 53019.
  • the polymer (s) having reactive silyl groups to be used according to the invention can be prepared, for example, from polyols, optionally diisocyanates and organofunctional silanes.
  • polyols or polyol compounds a plurality of at least two hydroxyl-bearing polymers can in principle be used, examples being polyesters, polyols, hydroxyl-containing polycaprolactones, hydroxyl-containing polybutadienes, polyisoprenes, dimer diols or OH-terminated polydimethylsiloxanes and their hydrogenation or hydroxyl groups -containing polyacrylates or polymethacrylates.
  • polyols to polyoxyalkylenes, in particular polyethylene oxides and / or polypropylene oxides.
  • Polyols containing polyethers as a polymer backbone have a flexible and elastic structure not only at the end groups but also in the polymer backbone. This can be used to produce compositions which have once again improved elastic properties.
  • Polyethers are not only flexible in their backbone but also stable at the same time. For example, polyethers are not attacked or decomposed by water and bacteria, in contrast to, for example, polyesters.
  • polyethylene oxides and / or polypropylene oxides whose molecular weight M n is between 500 and 20 000 g / mol (Dalton), the terminal unsaturation being less than 0.02 meq / g.
  • polyoxyalkylenes in particular polyethylene oxides or polypropylene oxides, which have a polydispersity PD of less than 2, preferably less than 1.5, in particular less than 1.3.
  • the molecular weight M n is understood to mean the number average molecular weight of the polymer. This, as well as the weight-average molecular weight M w , can be determined by gel permeation chromatography (GPC, also: SEC). This method is known to the person skilled in the art.
  • polyols are used as polyoxyalkylene polymers which have a narrow molecular weight distribution and thus low polydispersity. These can be produced, for example, by the so-called double metal cyanide catalysis (DMC catalysis).
  • DMC catalysis double metal cyanide catalysis
  • These polyoxyalkylene polymers are generally distinguished by a particularly narrow molar mass distribution, by a high average molecular weight and by a very low number of double bonds at the ends of the polymer chains.
  • Such polyoxyalkylene polymers have a polydispersity PD (M w / M n ) of at most 1.7.
  • Particularly preferred organic backbones are, for example, polyethers having a polydispersity of about 1:01 to about 1.3, more preferably about 1.05 to about 1.18, for example about 1.08 to about 1.1.1 or about 1.12 to about 1, 14.
  • these polyethers have an average molecular weight (M n ) of from about 500 to about 20,000 g / mol, in particular from about 5,000 to about 18,000 g / mol.
  • M n average molecular weight
  • Particularly preferred are polyethers having average molecular weights of about 10,000 to about 18,000 g / mol, in particular having average molecular weights of about 12,000 to about 18,000 or 15,000 to 18,000 g / mol.
  • the polyether compound or polyol consisting of at least two identical or different polyoxyalkylene blocks may be reacted in a preliminary reaction with a diisocyanate at a stoichiometric excess of the polyol compounds over the diisocyanate compound to give a polyurethane prepolymer which is hydroxyl terminated.
  • isocyanatosilanes or isocyanato-functional alkoxysilanes for example, the following isocyanatosilanes are suitable:
  • Methyldimethoxysilylmethylisocyanat Ethyldimethoxysilylmethylisocyanat, Methyldiethoxysilylmethylisocyanat, Ethyldiethoxysilylmethylisocyanat, Methyldimethoxy- silylethylisocyanat, Ethyldimethoxysilylethylisocyanat, Methyldiethoxysilylethylisocyanat, Ethyldiethoxysilylethylisocyanat, Methyldimethoxysilylpropylisocyanat, Ethyldimethoxysilyl- propyl isocyanate, diethoxysilylbutylisocyanat Methyldiethoxysilylpropylisocyanat, Ethyldiethoxysilylpropylisocyanat, Methyldimethoxysilylbutylisocyanat, Ethyldimeth
  • methyldimethoxysilylmethyl isocyanate methyldiethoxysilylmethyl isocyanate, methyldimethoxysilylpropyl isocyanate and ethyldimethoxysilylpropyl isocyanate or their trialkoxy analogues, in particular trimethoxysilylpropyl isocyanate or 3-isocyanatopropyltrimethoxysilane or triethoxysilylpropyl isocyanate or 3-isocyanatopropyltriethoxysilane.
  • the isocyanatosilane (s) are used in at least a stoichiometric amount to the hydroxyl groups of the polyol, but is preferably a small stoichiometric excess of the isocyanatosilanes over the hydroxyl groups of the polyol. This stoichiometric excess is between 0.5 and 10, preferably between 1, 2 and 2 equivalents of isocyanate groups based on the hydroxyl groups.
  • diisocyanates For the conversion of the polyether compound (s) of the upstream reaction to an alternative hydroxyl terminated polyurethane prepolymer, the following diisocyanates can be used:
  • cycloalkyl of MDI for example completely hydrogenated MDI (H12-MDI), alkyl substituted diphenylmethane diisocyanates, for example mono-, di-, tri- or tetraalkyl as well as their partially or completely hydrogenated cycloalkyl, 4,4 '-Diisocyanatophenylperfluorethan, Phthalcic - Re-bis-isocyanatoethyl ester, 1-chloromethylphenyl-2,4- or 2,6-diisocyanate, 1-bromomethylphenyl-2,4- or 2,6-diisocyanate, 3,3-bis-chloromethyl ether-4 , 4 ' -Diphenyldiisocyanat, sulfur-containing diisocyanates, as obtainable by reacting 2 moles of diisocyanate with 1 mol of thiodiglycol or Dihydroxydihexylsulfid, the di
  • the polyether compound in a first step, can be converted with one of the aforementioned diisocyanates in stoichiometric excess to an isocyanate-functional prepolymer, which is subsequently reacted with an aminosilane to a polymer having reactive silyl groups.
  • compositions according to the invention contain from 10 to 50% by weight, in particular from 15 to 35% by weight, of polymer (s) having reactive silyl groups, based on the total weight of the compositions.
  • the reactive silyl groups of the preferred polymer (s) have the following general formula:
  • the radicals R 1 to R 6 each independently represent a linear or branched, saturated or unsaturated hydrocarbon radical having 1 to about 24 C atoms, in particular 1, 2, 3 or 4 C atoms, a saturated or unsaturated cycloalkyl radical 4 to about 24 carbon atoms or an aryl radical having 6 to about 24 carbon atoms
  • the silyl group carries a trialkoxy or dialkoxy group.
  • polymers which contain di- or trialkoxysilyl groups have highly reactive attachment sites which enable rapid curing, high degrees of crosslinking and thus good final strengths.
  • Another advantage of such polymers containing alkoxy groups is the fact that when cured under the influence of moisture alcohols are formed, which are harmless in the released amounts and evaporate. Therefore, such compositions are particularly suitable for the home improvement sector.
  • dialkoxysilyl groups is that the corresponding compositions after curing are more elastic, softer and more flexible than systems containing trialkoxysilyl groups. They are therefore particularly suitable for use as sealants. In addition, they cease even less alcohol when curing and are therefore of particular interest when the amount of alcohol released is to be reduced.
  • trialkoxysilyl groups on the other hand, a higher degree of crosslinking can be achieved, which is particularly advantageous if a harder, stronger mass is desired after curing.
  • trialkoxysilyl groups are more reactive, ie they crosslink faster and thus reduce the required amount of catalyst; and they have advantages in the "cold flow" - the dimensional stability of a corresponding adhesive under the influence of force and possibly temperature action - on.
  • alkoxy groups in particular methoxy, ethoxy, propyloxy and butoxy groups are selected.
  • R 3 and R 4 are a methyl group.
  • compounds having alkoxysilyl groups have different reactivities in chemical reactions. Within the alkoxy groups, the methoxy group shows the greatest reactivity. It is thus possible to resort to silyl groups of this type if particularly rapid curing is desired.
  • higher Aliphatic radicals such as ethoxy cause an already lower reactivity of the terminal alkoxysilyl group compared to methoxy groups and can advantageously be used for the development of graded crosslinking rates.
  • the preparation or composition according to the invention additionally contains filler (s).
  • filler for example, precipitated and ground chalks with or without surface treatment, limestone, precipitated and / or fumed silica, zeolites, bentonites, magnesium carbonate, kieselguhr, clay, clay, talc, titanium oxide, iron oxide, zinc oxide, sand, quartz, flint, mica are suitable here. Glass powder and other ground minerals.
  • organic fillers can be used, in particular carbon black, graphite, wood fibers, wood flour, sawdust, pulp, cotton, cotton, wood chips, chaff, chaff, ground walnut shells and other fiber short cuts.
  • short fibers such as glass fiber, glass filament, polyacrylonitrile, carbon fiber, Kevlar fiber or even polyethylene fibers can be added.
  • Aluminum powder is also suitable as a filler.
  • the pyrogenic and / or precipitated silicas advantageously have a BET surface area of from 10 to 90 m 2 / g, in particular from 35 to 65 m 2 / g. When used, they do not cause any additional increase in the viscosity of the preparation according to the invention, but contribute to an enhancement of the cured preparation.
  • a highly disperse silica having a BET surface area of 45 to 55 m 2 / g, in particular having a BET surface area of about 50 m 2 / g.
  • Such silicas have the additional advantage of a 30 to 50% shortened incorporation time compared to silicic acids with a higher BET surface area.
  • Another advantage is that the above-mentioned fumed silica can be incorporated into the compositions in a considerably higher concentration without impairing the flow properties.
  • pyrogenic and / or precipitated silicas having a higher BET surface area, advantageously 100-250 m 2 / g, in particular 110-170 m 2 / g, as filler. Due to the higher BET surface area, one can achieve the same effect, eg reinforcement of the cured preparation, at a lower weight proportion of silica. Thus, one can use other substances to improve the preparation according to the invention in terms of other requirements.
  • the fillers are preferably used in an amount of 1 to 80 wt .-%, preferably of greater than or equal to 5, in particular greater than or equal to 20 wt .-%, based on the total weight of the composition.
  • the formulations further contain silane condensation catalyst (s). These may preferably be selected from the group consisting of titanium, tin, zinc, aluminum, iron, vanadium or hafnium compounds, heterocyclic organic amines, aminosilanes or mixtures thereof.
  • the metal compounds used are preferably their carboxylates of long-chain carboxylic acids or chelates based on ⁇ -dicarbonyl compounds.
  • the corresponding carboxylates of the dialkyltin compounds can also be used.
  • alkyl groups the C 4 to C 2 compounds come into question.
  • C 4 to C 36 saturated, monounsaturated or polyunsaturated monocarboxylic acids can be used in particular as the carboxylic acids.
  • arachidic acid n-eicosanoic acid
  • arachidonic acid all-cis-5,8,1 1, 14-eicosatetraenoic acid
  • behenic acid docosanoic acid
  • butyric acid butanoic acid
  • caprolearic acid 9-decenoic acid
  • capric acid n- Decanoic acid
  • caproic acid n-hexanoic acid
  • caprylic acid n-octanoic acid
  • cerotic acid hexacosanoic acid
  • cetoleic acid cis-11-docosenoic acid
  • clupanodonic acid all-cis-7,10, 13, 16, 19-docosapentaenoic acid
  • Eleostearic acid trans-9-trans-11-cis-13-octadeca-9, 11, 13-trienoic acid
  • enanthic acid (1-hexanecarboxylic acid
  • erucic acid cis
  • Suitable ⁇ -dicarbonyl compounds are acetylacetone, alkyl acetoacetate, dialkylmalonates, benzoylacetic acid esters, dibenzoylmethane, benzoylacetone, dehydroacetacetic acid.
  • heterocyclic organic amines which can be used are N-methylpyrrolidine, N-methylpiperidine, N, N-dimethylpiperazine, diaza-bicyclo-octane (DABCO), N- (2-hydroxyethoxyethyl) -2-azanorbornane, 1,8-diazadicyclo ( 5.4.0) undecene-7 (DBU), N-dodecyl-2-methylimidazole, N-methylimidazole, 2-ethyl-2-methylimidazole, N-methylmorpholine, bis (2- (2,6-dimethyl-4-morpholino) ethyl) - (2- (4-morpholino) ethyl) amine, bis (2- (2,6-dimethyl-4-morpholino) ethyl) - (2- (2,6-diethyl-4-morpholino) ethyl) amine , Tris (2- (4-morpholino) ethyl) amine,
  • heterocyclic amines In addition to the abovementioned heterocyclic amines, it is also possible according to the invention to use amine complexes of boron halides, in particular boron trifluoride, or boronalkylene as silane condensation catalysts (B).
  • Suitable amine components in this case are both the abovementioned heterocyclic amines and also simple lower alkylamines or diamines, specifically ethylamine, propylamine, butylamine and the aminosilanes mentioned elsewhere.
  • the catalyst preferably mixtures of several catalysts, are used in an amount of 0.001 to about 5 wt .-% based on the total weight of the composition.
  • the preparations or compositions according to the invention contain at least one urea preparation, preferably in the form of a solution of a urea urethane or urethane urethane polymer, if appropriate in the presence of a lithium salt, such as lithium chloride or lithium nitrate, in an aprotic solvent.
  • a lithium salt such as lithium chloride or lithium nitrate
  • the urea urethane is composed of a monofunctional C 4 to C 22 alkyl alcohol or cycloalkyl alcohol, a diisocyanate and a diamine (or. produced).
  • the preparation of such urea-urethanes is described in the following documents: DE 19919482 C2, DE 10039837 C2 or DE 10 2006 012999 A.
  • Monofunctional alcohols are reacted with a molar excess, for example a 1.5 to 5-fold molar excess, diisocyanate.
  • the unreacted parts of diisocyanate removed from the reaction mixture and the resulting monoisocyanate adducts with diamines, if appropriate in the presence of a lithium salt, converted to urea urethanes or urea urethane polymers.
  • Suitable aprotic solvents are, for example, N-methylpyrrolidone, N-ethylpyrrolidone, N-butylpyrrolidone, N-cyclohexylpyrrolidone, DMSO, dimethylformamide or other aprotic solvents known to the person skilled in the art.
  • Suitable monohydric alcohols are butanol, decanol, cyclohexanol, tridecanol, in particular i-tridecanol.
  • polyfunctional alcohols e.g. Dialcohols, such as e.g. Methoxypolyethylene glycol, or trialcohols, e.g. Butyl triglycol, to be used.
  • diisocyanate in particular toluene diisocyanate (TDI) is suitable.
  • TDI toluene diisocyanate
  • other diisocyanates can also be used, for example the diisocyanates described above, which can be used for the conversion of the polyether compound (s) of the upstream reaction into a hydroxyl-terminated polyurethane prepolymer.
  • Suitable diamines are, for example, xylylenediamine or hexamethylenediamine.
  • the proportion of nonvolatile compounds in the urea preparations used according to the invention is preferably 25-60% by weight, in particular 40-55% by weight, particularly preferably about 50% by weight.
  • the proportion of lithium salts in the urea preparations is preferably 1-3% by weight.
  • compositions according to the invention preferably contain from 0.1 to 5% by weight, in particular from 1 to 2% by weight, of urea preparation (s), based on the total weight of the compositions.
  • the preparations according to the invention may contain, in addition to the abovementioned, further auxiliaries and additives which impart improved elastic properties, improved resilience, sufficiently long processing time, fast curing rate and low residual tackiness to these preparations.
  • auxiliaries and additives include, for example, plasticizers, stabilizers, antioxidants, fillers, thinners or reactive diluents, drying agents, adhesion promoters and UV stabilizers, Fungicides, flame retardants, pigments, optionally further theological auxiliaries, color pigments or color pastes and / or, if appropriate, also small amounts of solvent.
  • Suitable plasticizers are, for example, adipic acid esters, azelaic acid esters, benzoic acid esters, butyric acid esters, acetic acid esters, esters of higher fatty acids containing from about 8 to about 44 carbon atoms, esters containing OH groups or epoxidized fatty acids, fatty acid esters and fats, glycolic esters, phosphoric esters, phthalic acid esters, from 1 to 12 C-atoms containing linear or branched alcohols, propionic acid esters, sebacic acid esters, sulfonic acid esters, thiobutyric acid esters, trimellitic acid esters, citric acid esters and esters based on nitrocellulose and polyvinyl acetate, and mixtures of two or more thereof.
  • asymmetric esters of adipic acid monooctyl ester with 2-ethylhexanol (Edenol DOA, Fa. Cognis Germany GmbH, Dusseldorf) or esters of abietic acid.
  • DOP dioctyl phthalate
  • DIUP diisoundecyl phthalate
  • BBP butylbenzyl phthalate
  • DOA dioctyl adipate
  • Disodecyl adipate diisodecylsuccinate
  • dibutyl sebacate dibutyl sebacate or butyl oleate
  • the pure or mixed ethers are also suitable as plasticizers monofunctional, linear or branched C 4 i 6 alcohols or mixtures of two or more different ethers of such alcohols, for example dioctyl (available as Cetiol OE. Cognis Germany GmbH, Dusseldorf).
  • plasticizers are end-capped polyethylene glycols.
  • polyethylene or polypropylene glycol di-C- M- alkyl ethers in particular the dimethyl or diethyl ethers of diethylene glycol or dipropylene glycol, and mixtures of two or more thereof.
  • antioxidants are to be understood as meaning antioxidants, UV stabilizers or hydrolysis stabilizers. Examples of these are the commercially available sterically hindered phenols and / or thioethers and / or substituted benzotriazoles such as, for example, Tinuvin 327 (Ciba Specialty Chemicals) and / or amines of the "HALS” type (Hindered Amine Light Stabilizer), such as, for example, Tinuvin 770 (cf. From Ciba Specialty Chemicals). It is preferred in the context of the present invention, when a UV stabilizer is used, which carries a silyl group and is incorporated in the final product during curing or curing.
  • the preparation according to the invention may contain up to about 2% by weight, preferably about 1% by weight, of stabilizers. Furthermore, the preparation according to the invention may further comprise up to about 7% by weight, in particular up to about 5% by weight, of antioxidants.
  • adhesion promoter is understood as meaning a substance which improves the adhesive properties of adhesive layers on surfaces.
  • adhesion promoter one can e.g. the following substances are used: polyalkylene glycols reacted with isocyanatosilanes (for example Synalox 100-50B, DOW), carbamatopropyltrimethoxysilane, alkyltrimethoxysilane, alkyltriethoxysilane,
  • Methyltrimethoxysilane, methyltriethoxysilane and vinyltrimethoxysilane (Dynasylan VTMO, Evonik or Geniosil XL 10, Wacker), vinyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, octyltrimethoxysilane, tetraethoxysilane, vinyldimethoxymethylsilane (XL12, Wacker), vinyltriethoxysilane (GF56, Wacker), vinyltriacetoxysilane (GF62, Wacker), isooctyltrimethoxysilane (IO trimethoxy), isooctyltriethoxysilane (IO triethoxy, Wacker), N-trimethoxysilylmethyl-O-methylcarbamate (XL63, Wacker), N-dimethoxy (methyl) silylmethyl-O-methyl-carbamate
  • silane coupling agents in particular alkoxysilanes, with a
  • (further) functional group such as e.g. an amino group, a mercapto group, a
  • Epoxy group a carboxyl group, a vinyl group, an isocyanate group, a
  • Isocyanurate group or a halogen examples of such low molecular weight organofunctional silanes are ⁇ -mercaptopropyltrimethoxysilane, ⁇ -mercaptopropyltriethoxysilane, ⁇ -mercaptopropylmethyldimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane,
  • adhesion promoters are in particular aminosilanes (aminofunctional
  • Alkoxysilanes or aminoalkyl-alkoxysilanes such as, for example, ⁇ -aminopropyltrimethoxysilane, Aminopropyltriethoxysilane, ⁇ -aminopropyltriisopropoxysilane, y-
  • silane-functional adhesion promoters simultaneously have a drying and / or diluting action (reactive diluents) in the preparation or composition.
  • These adhesion promoters are preferably used in amounts of between 0.1 and 15% by weight, in particular between 1 and 5% by weight, based on the total weight of the composition.
  • compositions or preparations according to the invention have the following composition:
  • compositions contain:
  • compositions according to the invention are preferably isocyanate-free, ie the compositions no longer contain free NCO groups, or the residual NCO content is less than 1.
  • isocyanate-free Compositions are understood to mean the proportion by weight of the free NCO groups present in the composition, based on the total weight of the composition, according to the general expert's understanding.
  • the residual NCO content is predetermined by the stoichiometry of the starting materials used, that is, it is an imputed value.
  • the residual NCO content it is assumed that the NCO groups present in the starting materials and NCO-reactive groups completely react with one another. This could be confirmed by random examinations - titrametrically by standard method.
  • Low isocyanate contents or isocyanate-free mixtures are preferred from a toxicological point of view.
  • a low residual NCO content on curing has a positive effect in that the alcohols released by the hydrolysis of the alkoxysilyl groups are trapped by the NCO groups.
  • the remaining free, highly reactive isocyanate groups to toxicologically harmless urethane groups from, on the other hand can not be unwanted side reactions, eg. B. transesterifications, are triggered.
  • composition or preparation according to the invention is carried out by known methods by intimately mixing the ingredients in suitable dispersing aggregates, for.
  • suitable dispersing aggregates for.
  • fast mixer kneader, planetary mixer, planetary dissolver, internal mixer, so-called “Banbury mixer”, twin-screw extruder and similar mixing units known in the art.
  • the preparations according to the invention have such a thixotropy immediately after application that they can be applied both in thick vertical layers (for example with the trowel) and as a paint (with brush or roller).
  • the flow behavior is so pronounced that thicker layers in the vertical with a job are possible without slipping.
  • the surface still runs with brush application in such a way that a smooth surface is created.
  • the ambient air humidity they harden to polymeric coatings after application. Skin formation preferably takes about 30 to 60 minutes.
  • the curing rate is preferably 1 to 5 mm per day, especially 2 to 3 mm per day.
  • Another object of the present invention is the use of the one-component, moisture-curing composition according to the invention as an adhesive, sealant or coating agent, in particular for the sealing of structures.
  • the invention will be explained in more detail, the selection of examples is not intended to represent a limitation of the scope of the subject invention.
  • Plasticizers, fillers and other additives produced.
  • the coating composition of Comparative Example 5 is the commercial product "Aqua Blocker” from Bostik.
  • Test conditions for the mechanical properties of the cured formulations The above-mentioned mixtures were applied with a thickness of 2 mm to glass plates covered with polyether film. After 7 days of storage (23 ° C, 50% relative humidity), samples (S2 specimens) were punched out of these films and the mechanical data (E-modulus at 50% elongation, elongation at break and breaking force) was modeled on DIN EN 27389 and DIN EN 28339 determined. Furthermore, the tensile shear strength of a bond between two test specimens made of beech plywood was tested to assess the bond strength.
  • Geniosil GF96 3- (aminopropyl) trimethoxysilane
  • Tinuvin 327 2- (2'-Hydroxv-3 ', 5'-di-tert-butylphenyl) -5-chlorobenzotriazole
  • Tinuvin 770 DF bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate
  • Pigment JP-41607-2 Slurry of titanium dioxide in di-isoundecyl phthalate
  • Byk 410 urea preparation Byk; modified urea with 1% by weight LiCl dissolved in N-methylpyrrolidone (52% nonvolatiles)

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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)
  • Adhesives Or Adhesive Processes (AREA)
  • Paints Or Removers (AREA)

Abstract

La présente invention concerne des compositions contenant un seul composant, sans isocyanates et durcissant à l'humidité qui contiennent a. au moins un polymère ayant des groupes silyle réactifs, b. au moins une charge, c. au moins un catalyseur de condensation du silane, e. au moins une préparation à base d'urée. Ces préparations sont adaptées à une utilisation en tant qu'agent de revêtement, agent adhésif ou mastic pour assurer l'étanchéité de constructions.
PCT/EP2009/060799 2008-08-20 2009-08-20 Composition de revêtement résistante à l’eau et durcissant à l’humidité qui contient un polymère ayant des groupes silyle réactifs WO2010020678A1 (fr)

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DE102008038488A DE102008038488A1 (de) 2008-08-20 2008-08-20 Feuchtigkeitshärtende wasserfeste Beschichtung
DE102008038488.7 2008-08-20

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BE1027545B1 (nl) * 2019-09-02 2021-03-31 Fourny Nv Adhesief en applicator voor het aanbrengen van dit adhesief

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BE1027545B1 (nl) * 2019-09-02 2021-03-31 Fourny Nv Adhesief en applicator voor het aanbrengen van dit adhesief

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