Compositions based on silane-terminated polymers and acetylene black

By combining acetylene black with polymers containing silane groups, the problem of pre-drying carbon black compositions in the prior art has been solved, achieving efficient production and excellent thixotropic and viscosity properties. It is suitable for adhesives, sealants and coatings, and is particularly suitable for bonding different substrates.

CN115151584BActive Publication Date: 2026-03-10SIKA TECH AG
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2021-03-10
Publication Date
2026-03-10

AI Technical Summary

Technical Problem

Existing polymer compositions containing silane groups require laborious pre-drying when using carbon black, and it is difficult to achieve efficient production and excellent thixotropic and viscosity properties.

Method used

Using acetylene black as a filler, combined with polymers containing silane groups, reduces or eliminates the pre-drying step, and ensures the stability and rheological properties of the composition during production and use through the low water absorption and suitable equilibrium moisture content of acetylene black.

Benefits of technology

It achieves efficient production of compositions and excellent thixotropic and viscosity properties, suitable for adhesives, sealants and coatings, especially suitable for bonding different substrates, and can be extruded from the barrel without dripping, suitable for single-component and two-component systems.

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Abstract

This invention relates to compositions, particularly for use as adhesives, sealants, coatings or casting materials, comprising: - at least one polymer containing silane groups, - at least one acetylene black as a filler.
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Description

Technical Field

[0001] This invention relates to compositions, particularly compositions used as adhesives, sealants, coatings, or casting materials, comprising at least one polymer containing a silane group and carbon black. The invention also relates to the use of carbon black to achieve thixotropy and / or increase the viscosity of a composition, methods for bonding compositions, and articles thereby obtained. Existing technology

[0002] Compositions of silane-functionalized polymers or polymers containing silane groups, and their uses as adhesives, sealants, casting materials or coatings, are well known and have been described many times.

[0003] EP 1 256 595 A1 (Sika AG) describes, for example, a binder composition comprising a special silane crosslinked polymer and finely chopped, coated calcium carbonate and carbon black. Based on 100 g of polymer, there are 20-50 ml of finely chopped, coated calcium carbonate and carbon black, with the volume ratio of finely chopped, coated calcium carbonate to carbon black between 70 / 30 and 30 / 70. This binder composition is characterized by good mechanical properties, high volume resistivity, and good applicability.

[0004] The carbon black has a density of approximately 1.8 g / ml and a large surface area. Specifically, it refers to "Printex 60" type carbon black from Degussa Hüls. The carbon black must be dried before use.

[0005] EP 3 002 314 A1 (Sika Technology AG) discloses, for example, a two-component composition comprising at least one silane-containing polymer that is liquid at room temperature, at least one liquid epoxy resin, at least one polyetheramine, and at least one amino- or mercapto-silane. The composition may contain various organic or inorganic fillers such as fly ash, carbon black, graphite, etc.

[0006] EP 2 151 480 A1 (Shin-Etsu Chemical Co., Ltd) discloses silicone compositions suitable as adhesives and sealants, which exhibit improved oil resistance and improved adhesion to oily surfaces. To achieve these properties, oil-absorbing carbon powder, such as activated carbon, or carbon black, such as acetylene black, is incorporated.

[0007] However, a known drawback of carbon black is that it typically requires laborious pre-drying for use in compositions based on polymers containing silane groups. Furthermore, known formulations have the potential to improve their mechanical properties, adhesion, and applicability. Invention Overview

[0009] Therefore, the object of the present invention is to provide compositions, particularly adhesives, sealants, coatings, or castings, based on polymers containing silane groups, which can be produced with minimal effort and possess the best possible properties for practical use. In particular, compositions that eliminate the need for pre-drying of components should be provided, if possible. Additionally, compositions with thixotropic properties should be provided, such that they can be applied, for example, from a cartridge without dripping after application.

[0010] This objective is surprisingly achieved through the composition described in this invention. The composition comprises at least one polymer containing silane groups and at least one acetylene black as a filler.

[0011] The compositions of the present invention are easier to produce compared to corresponding compositions containing polymers with silane groups and, in some cases, other carbon blacks known from the prior art. This is particularly because acetylene black has a sufficiently low water absorption / equilibrium moisture content for use with polymers containing silane groups. This means that the initial carbon black drying step, which is necessary for most other carbon blacks, is not required during the production of the compositions, nor are the special measures necessary for storing carbon black required.

[0012] Furthermore, the use of acetylene black has proven advantageous for the rheological and mechanical properties of the compositions thus formulated. For example, adhesives, sealants, coatings, and casting materials can be produced, exhibiting optimal thixotropy and viscosity for many applications and simultaneously extruding from the barrel without any problems. The compositions also demonstrate high adhesion to various substrates.

[0013] The compositions of the present invention can be used with extreme flexibility. For example, the compositions can be formulated as adhesives, sealants, coatings, and casting materials. These can be provided as one-component and two-component systems.

[0014] The compositions of the present invention are particularly suitable for formulating one-component, water-curing adhesives containing silane groups, which are particularly suitable as adhesives for bonding vehicle windows without a primer. The compositions of the present invention are also particularly suitable for formulating two-component compositions based on a combination of a polymer containing silane groups and an epoxy resin, which are suitable for, for example, bonding, sealing, or coating very different substrate materials.

[0015] Further aspects of the invention are the subject of the additional independent claims. Particularly preferred embodiments of the invention are the subject of the dependent claims.

[0016] Methods of implementing the present invention

[0017] This invention provides compositions, particularly compositions for use as adhesives, sealants, coatings, or casting materials, comprising:

[0018] - At least one polymer containing silane groups

[0019] - At least one acetylene black is used as a filler.

[0020] In this document, the term "alkoxysilyl group" or simply "silyl group" refers to a silyl group that is attached to an organic group and has one to three, particularly two or three, hydrolyzable alkoxy groups on a silicon atom. Therefore, the term "polymer containing a silyl group" in this document means a polymer having at least a predominantly organic backbone that contains at least one silyl group attached to an organic group of the polymer and has one to three, particularly two or three, hydrolyzable alkoxy groups on a silicon atom. Polymers containing silyl groups are therefore not polydimethylsiloxane polymers (silicone polymers).

[0021] Accordingly, the term "organosilanes" or simply "silanes" refers to organic compounds having at least one silane group as defined above.

[0022] "Aminosilane", "mercaptosilane", or "hydroxysilane" refer to organosilanes that have amino, mercapto, or hydroxy groups in addition to silane groups on their organic groups.

[0023] The “silicon content” of polymers containing silane groups refers to the silicon content of the polymer based on 100% by weight of the polymer. Dilution of the polymer with solvents or plasticizers is not considered part of the polymer. Similarly, silane functional additives, such as adhesion-promoting organosilanes that may optionally be present in the composition, are not included in the silicon content of polymers containing silane groups. For the purposes of this invention, such substances are not considered polymers containing silane groups.

[0024] The "NCO content" of a polymer refers to the content of isocyanate groups in the polymer, expressed as a percentage by weight.

[0025] "Aromatic" isocyanate groups are groups that are directly bonded to aromatic carbon atoms.

[0026] Substances whose names begin with "poly" (e.g., polyamines or polyols) are substances that contain two or more functional groups that appear in their names in each molecule.

[0027] "Amino hydrogen" refers to the hydrogen atom in primary and secondary amino groups.

[0028] A "primary amine group" is an amine group that is attached to a single organic group and carries two hydrogen atoms; a "secondary amine group" is an amine group that is attached to two organic groups (which may also be part of a ring) and carries one hydrogen atom; and a "tertiary amine group" is an amine group that is attached to three organic groups (two or three of which may also be part of one or more rings) and does not carry any hydrogen atoms.

[0029] In this document, the term “viscosity” refers to dynamic viscosity or shear viscosity, which is defined by the ratio between shear stress and shear rate (velocity gradient) and is determined based on DIN EN ISO 3219-1994.

[0030] "Molecular weight" refers to the molar mass of a molecule or molecular residue (in grams per mole). "Average molecular weight" refers to the number-average molecular weight (Maverage) of a polydisperse mixture of oligomer or polymer molecules or molecular residues. n It is determined by gel permeation chromatography (GPC) using polystyrene as a standard, and especially by using tetrahydrofuran as the mobile phase and refractive index detector.

[0031] A substance or composition described as “storage stable” or “storable” is a substance or composition that can be stored at room temperature in a suitable container for an extended period, typically at least 3 months and up to 6 months or longer, without causing any change in its application or use properties to the extent relevant to its use.

[0032] "Room temperature" refers to a temperature of 23°C.

[0033] All industry standards and specifications mentioned in this document relate to the valid version as of the date of initial submission.

[0034] Weight percentage (wt%) refers to the proportion of a component of a polymer or composition based on the whole polymer or the whole composition, unless otherwise stated. The terms “mass” and “weight” are used synonymously in this document.

[0035] In this document, the dashed lines in the chemical formulas represent, in each case, the bonds between the substituents and the relevant molecular groups.

[0036] In this context, the term "carbon black" refers to industrial carbon black. This is typically produced in particulate form. Industrial carbon black consists of primary particles, usually having a size of 10 to 300 nanometers, that aggregate together to form agglomerates and clumps. Carbon black can be specialized to have specific properties, for example, through the properties of the production process and the process parameters chosen for this purpose, such as pressure, temperature, and raw materials.

[0037] Acetylene black, also known as acetylene carbon black, is one of many possible types of carbon black. Acetylene black is carbon black obtained by the incomplete combustion of acetylene. Acetylene black is chemically and / or physically different from other types of manufactured carbon black. Compared to other types of carbon black, acetylene black has particularly high purity and electrical conductivity. Examples of other types of carbon black are gas black, furnace black, lamp black, thermal black, channel black, or gloss black.

[0038] The acetylene black used in the composition has the following advantageous properties.

[0039] Preferably, the carbon content (C content) of the acetylene black is >98% by weight, especially >99% by weight, and most preferably >99.5% by weight.

[0040] The ash content of acetylene black is advantageously <0.1% by weight, especially <0.03% by weight, and preferably <0.015% by weight. The ash content is determined according to ASTM D1506-15.

[0041] Particularly preferred, the acetylene black has a carbon content of >99.5% by weight and a sulfur content of <0.05% by weight.

[0042] The acetylene black used in the composition preferably has an oil absorption value (OAN) of >150 ml / 100 g, more preferably >200 ml / 100 g, more preferably >250 ml / 100 g, and particularly >300 ml / 100 g. The oil absorption value is measured according to ASTM D 2414-19 standard.

[0043] More specifically, acetylene black has an oil absorption value of 150-400ml / 100g, preferably 200-375ml / 100g, particularly 250-350ml / 100g, and 275-325ml / 100g.

[0044] Preferably, acetylene black has a particle size of <115 μm. 2 / g, preferably <100m 2 / g, more preferably <80m 2 / g BET surface area. BET surface area was determined according to ASTM D6556-19a standard.

[0045] Particularly preferred, acetylene black has a BET surface area of ​​20-115 m². 2 / g, preferably 30-100m 2 / g, especially 50-90m 2 / g, especially 60-80m 2 / g.

[0046] The bulk density of acetylene black is particularly high, ranging from 0.02 to 0.6 g / cm³. 3 The preferred concentration is 0.05-0.2 g / cm³. 3 Especially 0.07-1.2 g / cm³ 3 .

[0047] Specifically, acetylene black has a dew point of 12°C in air and an equilibrium moisture content of <0.2% by weight at 23°C. The equilibrium moisture content is determined by the commonly known Karl Fischer titration.

[0048] Acetylene black preferably has a combination of two or more of the properties mentioned above. In particular, acetylene black simultaneously possesses the oil absorption value and the BET surface area. Acetylene black also particularly possesses the bulk density. Furthermore, preferably, acetylene black also possesses the equilibrium moisture content, and more preferably, it also possesses the carbon content.

[0049] When the compositions of the present invention are used to formulate one-component adhesives containing silane groups, acetylene black advantageously has an oil absorption value of 150-400 ml / 100 g, preferably 200-375 ml / 100 g, and simultaneously has a BET surface area of ​​30-100 m². 2 / g, especially 50-90m 2 / g, more preferably 60-80m 2 / g. Furthermore, it is advantageous when acetylene black also has the aforementioned equilibrium moisture content in this case. Acetylene black also particularly possesses the aforementioned bulk density.

[0050] When the compositions of the present invention are used to formulate two-component compositions based on a combination of a polymer containing silane groups and an epoxy resin, acetylene black advantageously has an oil absorption value of 250-350 ml / 100g, preferably 275-325 ml / 100g, and simultaneously has a BET surface area of ​​20-115 m². 2 / g, especially 80-115m 2 / g. Furthermore, it is advantageous when acetylene black also has the aforementioned equilibrium moisture content in this case. Acetylene black also particularly possesses the aforementioned bulk density.

[0051] Acetylene black advantageously constitutes 5-20% by weight, preferably 8-18% by weight, and particularly 10-15% by weight of the total composition. This achieves optimal properties.

[0052] Polymers containing silane groups are preferably liquids at room temperature.

[0053] Polymers containing silane groups have an average of 1.3 to 4, more preferably 1.5 to 3, and especially 1.7 to 2.8 silane groups per molecule. Polymers containing silane groups most preferably have an average of 1.7 to 2.3 silane groups per molecule.

[0054] Polymers containing silane groups preferably have a silicon content in the range of 0.7 wt% to 1.5 wt%, particularly 0.8 wt% to 1.2 wt%. Such compositions allow for a particularly advantageous combination of high strength and high ductility.

[0055] Polymers containing silyl groups preferably have an average molecular weight M n Within the range of 2000-30000 g / mol, preferably 4000-20000 g / mol.

[0056] In the case of a one-component composition or a composition without a liquid epoxy resin, the polymer containing silane groups preferably has an average molecular weight M. n Within the range of 12000-30000 g / mol, preferably 13000-20000 g / mol.

[0057] When the composition additionally comprises a liquid epoxy resin, the polymer containing silane groups preferably has an average molecular weight M. n Within the range of 2000-10000 g / mol, more preferably 3000-8000 g / mol, and especially 4000-7000 g / mol.

[0058] Polymers containing silane groups preferably have a majority of polyoxyalkylene units, especially polyoxypropylene units.

[0059] Polymers containing silane groups preferably have silane groups of formula (I).

[0060]

[0061] in

[0062] n is 1, 2, or 3, especially 2 or 3;

[0063] R 1 It is a straight-chain or branched monovalent hydrocarbon group with 1-5 carbon atoms.

[0064] R 2 It is a straight-chain or branched divalent hydrocarbon group having 1-12 carbon atoms and optionally having a cyclic and / or aromatic moiety and optionally one or more heteroatoms, especially an amide group, a carbamate group or a morpholino group.

[0065] X is O, S, or NR. 3 , where R 3 It is a hydrogen atom or a straight-chain or branched hydrocarbon group having 1-20 carbon atoms, which optionally has a cyclic moiety and optionally has an alkoxysilyl, ether, or carboxylic acid ester group.

[0066] Preferably, n is 3. Such a composition cures particularly quickly and allows for particularly high strength.

[0067] Preferably, R 1 It is methyl, ethyl, or isopropyl.

[0068] More preferably, R 1 It is methyl. Polymers containing silane groups are particularly reactive.

[0069] Even more preferably, R 1It is ethyl. Polymers containing silyl groups are particularly stable in storage and have favorable toxicological properties.

[0070] X is preferably O or NR 3 .

[0071] Preferably, R 3 It is an aliphatic group with 6-20 carbon atoms that is H, butyl, phenyl, or optionally has an ether or carboxylic acid group.

[0072] More preferably, X is NR 3 and R 3 yes Where R 4 It is methyl or ethyl, especially ethyl. Such polymers containing silane groups are readily available and allow for particularly high strength along with high ductility and stability.

[0073] When X = NR 3 At that time, R 2 Preferably, it is 1,3-propylidene or 1,4-butylidene, wherein the butylidene group may be substituted by one or two methyl groups, and more preferably 1,3-propylidene.

[0074] When X = 0, R 2 Preferably, it is a divalent hydrocarbon group having 6-12 carbon atoms, which has an amide group, a carbamate group, or a morpholino group, especially the formula... . group.

[0075] Preferred polymers containing silane groups allow compositions to have a particularly attractive combination of high strength and high ductility.

[0076] Polymers containing silane groups are preferably obtained by reacting at least one polymer containing isocyanate groups with at least one amino-, mercapto-, or hydroxy-silane.

[0077] The isocyanate-containing polymers derived from polymers containing silane groups preferably have an NCO content in the range of 0.25 wt% to 4 wt%, particularly 0.3 wt% to 3.5 wt%, particularly 0.4 wt% to 2.5 wt%. This is especially true when the composition is a one-component composition or a composition without a liquid epoxy resin.

[0078] When the composition comprises a liquid epoxy resin, the polymer containing isocyanate groups preferably has an NCO content in the range of 1.2-4% by weight, particularly 1.2%-2.8% by weight. Such polymers containing isocyanate groups allow for a silane group content according to the invention when reacting with preferred silanes.

[0079] Polymers containing isocyanate groups are instead obtained, in particular, by the reaction of at least one polyol and at least one diisocyanate.

[0080] The reaction is preferably carried out in the absence of moisture at a temperature in the range of 20-160°C, especially 40-140°C, optionally in the presence of a suitable catalyst.

[0081] The preferred NCO / OH molar ratio is in the range of 1.3 / 1 to 2.5 / 1.

[0082] Suitable polyols for preparing polymers containing isocyanate groups are polyols that are liquid at room temperature, especially the following commercially available polyols or any mixtures thereof:

[0083] - Polyether polyols, especially polyalkylene glycols and / or polyalkylene triols, particularly polymers of ethylene oxide or 1,2-epoxypropane or 1,2- or 2,3-epoxybutane or oxetane or tetrahydrofuran or mixtures thereof, wherein these can be polymerized by means of a starting molecule having two or three active hydrogen atoms, especially a starting molecule such as water, ammonia, or a compound having two or more OH or NH groups, such as 1,2-ethylene glycol. 1,2- or 1,3-propanediol, neopentyl glycol, diethylene glycol, triethylene glycol, isomeric dipropylene glycol or tripropylene glycol, isomeric butanediol, pentylene glycol, hexanediol, heptanediol, octanediol, nonanediol, decanediol, undecanediol, cyclohexyl-1,3- or -1,4-diethanol, bisphenol A, hydrogenated bisphenol A, 1,1,1-trimethylolethane, 1,1,1-trimethylolpropane, glycerol or aniline, or mixtures of the compounds mentioned above.

[0084] Preferred polyether polyols are polyoxypropylene glycol or polyoxypropylene triol, or so-called ethylene oxide-terminated (EO-terminated) polyoxypropylene glycol or triol. The latter is a polyoxyethylene / polyoxypropylene copolyol, which is obtained, in particular, by further alkoxylation of the polyoxypropylene glycol or triol with ethylene oxide at the end of the polypropoxylation reaction and thus has primary hydroxyl groups.

[0085] The preferred polyether polyol has an unsaturation degree of less than 0.02 meq / g, especially less than 0.01 meq / g.

[0086] - Polyether polyester polyol.

[0087] - Polyacrylate polyols and polymethacrylate polyols.

[0088] - Polyacrylate or polymethacrylate polyol.

[0089] - Polyhydroxy functional fats or oils, such as natural fats and oils, especially castor oil, or polyols obtained through chemical modification of natural fats and oils - are called oleochemical polyols.

[0090] - Polyhydric polyols, also known as oligohydric alcohols, such as, in particular, polyhydroxy-functionalized polyolefins, polyisobutylene, and polyisoprene; polyhydroxy-functionalized ethylene / propylene, ethylene / butene, or ethylene / propylene / diene copolymers, such as those produced by Kraton Polymers; polyhydroxy-functionalized dienes, especially 1,3-butadiene, which may also be produced, particularly, by anionic polymerization; polyhydroxy-functionalized copolymers of dienes such as 1,3-butadiene or mixtures of dienes with vinyl monomers such as styrene, acrylonitrile, vinyl chloride, vinyl acetate, vinyl alcohol, isobutylene, or isoprene, especially polyhydroxy-functionalized acrylonitrile / butadiene copolymers, such as those produced, particularly by epoxides or amino alcohols and carboxyl-terminated acrylonitrile / butadiene copolymers (which may be produced, for example, by... CTBN or CTBNX or ETBN (the names are available commercially from Emerald Performance Materials); or hydrogenated polyhydroxy functionalized polymers or copolymers of dienes.

[0091] Polyether polyols are preferred, especially polyoxyalkylene glycols or triols.

[0092] Polyoxypropylene glycol or polyoxypropylene triol having terminal ethylene oxide groups is particularly preferred.

[0093] Polyols with an average OH functionality in the range of 1.6-3 are preferred, especially diols with an average OH functionality in the range of 1.8-2.

[0094] Preferably, it has an average molecular weight M n Polyols in the range of 1000-20000 g / mol, especially 2000-16000 g / mol.

[0095] In the preparation of polymers containing isocyanate groups, a certain proportion of di- or polyfunctional alcohols may also be included.

[0096] Polymers containing isocyanate groups are preferably obtained by reacting at least one polyoxypropylene glycol having an OH value in the range of 5-58 mg KOH / g, especially 6-40 mg KOH / g and optionally terminal ethylene oxide groups with at least one diisocyanate.

[0097] The preparation of polymers containing isocyanate groups may optionally include at least one other polymer, particularly polyoxypropylene triols optionally having terminal ethylene oxide groups.

[0098] Suitable diisocyanates for preparing polymers containing isocyanate groups are diisocyanates having aliphatic isocyanate groups, especially hexane-1,6-diisocyanate (HDI), 2,2(4),4-trimethylhexamethylene-1,6-diisocyanate (TMDI), cyclohexane-1,3- or 1,4-diisocyanate, 1-isocyanate-3,3,5-trimethyl-5-isocyanate-methylcyclohexane (isophorone diisocyanate or IPDI), perhydrodiphenylmethane-2,4'- or 4,4'-diisocyanate (HMDI), 1,3- or 1,4- Bis(isocyanatomethyl)cyclohexane or m- or p-xylene diisocyanate (XDI), and diisocyanates having aromatic isocyanate groups, especially diphenylmethane-4,4'-diisocyanate, optionally containing a certain proportion of diphenylmethane-2,4'- and / or 2,2'-diisocyanate (MDI), toluene-2,4-diisocyanate or a mixture thereof with toluene-2,6-diisocyanate (TDI), phenylene-1,4-diisocyanate (PDI) or naphthalene-1,5-diisocyanate (NDI), and mixtures of said diisocyanates.

[0099] HDI, IPDI, MDI or TDI are preferred, especially IPDI, MDI or TDI, with MDI or TDI being the most preferred.

[0100] In a preferred embodiment of the invention, the polymer containing isocyanate groups has aromatic isocyanate groups. The resulting polymer containing silane groups allows for inexpensive compositions with particularly high strength.

[0101] More specifically, the aromatic isocyanate group is derived from diphenylmethane-4,4'-diisocyanate, optionally containing a certain proportion of diphenylmethane-2,4'- and / or 2,2'-diisocyanate (MDI), or toluene-2,4-diisocyanate or a mixture thereof with toluene-2,6-diisocyanate (TDI).

[0102] The amino- or mercapto- or hydroxysilane used for reaction with polymers containing isocyanate groups preferably has formula (II).

[0103]

[0104] Where n and R 1 R 2 And X as defined previously.

[0105] The aminosilanes suitable for reaction with polymers containing isocyanate groups are primary aminosilanes or secondary aminosilanes. Preferred adducts are 3-aminopropyltrimethoxysilane, 3-aminopropyldimethoxymethylsilane, 4-aminobutyltrimethoxysilane, 4-amino-3-methylbutyltrimethoxysilane, 4-amino-3,3-dimethylbutyltrimethoxysilane, N-butyl-3-aminopropyltrimethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, adducts formed from primary aminosilanes such as 3-aminopropyltrimethoxysilane, 3-aminopropyldimethoxymethylsilane, or N-(2-aminoethyl)-3-aminopropyltrimethoxysilane and Michael acceptors such as acrylonitrile, (meth)acrylate, (meth)acrylamide, maleate diester or fumarate diester, citrate diester or itacrate diester, especially N-(3-trimethoxysilylpropyl)aminosuccinate diethyl ester or N-(3-dimethoxymethylsilylpropyl)aminosuccinate diethyl ester. Equally suitable are the described analogues of aminosilanes, wherein the ethoxy group replaces the methoxy group on the silicon.

[0106] Mercaptosilanes, especially 3-mercaptopropyltrimethoxysilane, 3-mercaptopropyldimethoxymethylsilane, or analogs of these mercaptosilanes having an ethoxy group replacing the methoxy group on silicon, are suitable for reaction with polymers containing isocyanate groups.

[0107] Hydroxysilanes suitable for reaction with polymers containing isocyanate groups can be obtained, in particular, by addition of aminosilanes to lactones, lactides, or cyclic carbonates.

[0108] Preferred hydroxysilanes of this type are N-(3-triethoxysilylpropyl)-2-hydroxypropamide, N-(3-trimethoxysilylpropyl)-2-hydroxypropamide, N-(3-triethoxysilylpropyl)-4-hydroxypentamide, N-(3-triethoxysilylpropyl)-4-hydroxyoctamide, N-(3-triethoxysilylpropyl)-5-hydroxydecamide, or N-(3-triethoxysilylpropyl)-2-hydroxypropylcarbamate.

[0109] In addition, suitable hydroxysilanes can be obtained by addition from aminosilanes to epoxides or from amino to epoxysilanes.

[0110] Preferred hydroxysilanes of this type are 2-morpholino-4(5)-(2-trimethoxysilylethyl)cyclohexyl-1-ol, 2-morpholino-4(5)-(2-triethoxysilylethyl)cyclohexyl-1-ol, or 1-morpholino-3-(3-(triethoxysilyl)propoxy)prop-2-ol.

[0111] For reactions with polymers containing isocyanate groups, aminosilanes are preferred, especially diethyl N-(3-trimethoxysilylpropyl)aminosuccinate, diethyl N-(3-dimethoxymethylsilylpropyl)aminosuccinate, or diethyl N-(3-triethoxysilylpropyl)aminosuccinate.

[0112] In another advantageous embodiment, the composition further comprises:

[0113] - at least one liquid epoxy resin, and

[0114] - At least one polyamine, preferably having at least three amine hydrogens that are reactive to epoxy groups.

[0115] Suitable liquid epoxy resins are those of conventional technology that flow freely at room temperature and have a glass transition temperature of less than 25°C. These are obtained in a known manner, more particularly from compounds having at least two active hydrogen atoms, more particularly from polyphenols, polyols, or amines, through glycidization by reaction with epichlorohydrin.

[0116] Suitable liquid epoxy resins, especially aromatic liquid epoxy resins, particularly the following glycidylated products:

[0117] Bisphenol A, bisphenol F, or bisphenol A / F, where A represents acetone and F represents formaldehyde, are used as reactants in the preparation of these bisphenols. In the case of bisphenol F, positional isomers may also exist, especially those derived from 2,4'- or 2,2'-hydroxyphenylmethane.

[0118] -Dihydroxybenzene derivatives such as resorcinol, hydroquinone, or catechol;

[0119] Other bisphenols or polyphenols include bis(4-hydroxy-3-methylphenyl)methane, 2,2-bis(4-hydroxy-3-methylphenyl)propane (bisphenol C), bis(3,5-dimethyl-4-hydroxyphenyl)methane, 2,2-bis(3,5-dimethyl-4-hydroxyphenyl)propane, 2,2-bis(3,5-dibromo-4-hydroxyphenyl)propane, 2,2-bis(4-hydroxy-3-tert-butylphenyl)propane, 2,2-bis(4-hydroxyphenyl)butane (bisphenol B), 3,3-bis(4-hydroxyphenyl)pentane, 3,4-bis(4-hydroxyphenyl)hexane, 4,4-bis(4-hydroxyphenyl)heptane, 2,4-bis(4-hydroxyphenyl)-2-methylbutane, and 2,4-bis(3,5-dimethyl-4-hydroxyphenyl)-2-methyl Butane, 1,1-bis(4-hydroxyphenyl)cyclohexane (bisphenol Z), 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (bisphenol TMC), 1,1-bis(4-hydroxyphenyl)-1-phenylethane, 1,4-bis[2-(4-hydroxyphenyl)-2-propyl]benzene (bisphenol P), 1,3-bis[2-(4-hydroxyphenyl)-2-propyl]benzene (bisphenol M), 4,4'-dihydroxybiphenyl (DOD), 4,4'-dihydroxybenzophenone, bis(2-hydroxynaphth-1-yl)methane, bis(4-hydroxynaphth-1-yl)methane, 1,5-dihydroxynaphthyl, tris(4-hydroxyphenyl)methane, 1,1,2,2-tetra(4-hydroxyphenyl)ethane, bis(4-hydroxyphenyl) ether or bis(4-hydroxyphenyl) sulfone;

[0120] - The condensation products of phenol and formaldehyde obtained under acidic conditions, such as phenol-formaldehyde varnish or cresol-formaldehyde varnish, are also called bisphenol F-formaldehyde varnish.

[0121] -Aromatic amines such as aniline, toluidine, 4-aminophenol, 4,4'-methylenediphenyldiamine, 4,4'-methylenediphenyldi(N-methyl)amine, 4,4'-[1,4-phenylenebis(1-methylethoxy)]bisaniline (bisaniline P) or 4,4'-[1,3-phenylenebis(1-methylethoxy)]bisaniline (bisaniline M).

[0122] Other suitable liquid epoxy resins are aliphatic or alicyclic polyepoxides, especially

[0123] - Glycidyl ethers of the following substances: saturated or unsaturated, branched or unbranched, cyclic or open-chain, di-, tri-, or tetrafunctional C2-C 30 Alcohols, especially ethylene glycol, propylene glycol, butanediol, hexanediol, octanediol, polypropylene glycol, dimethylolcyclohexane, neopentyl glycol, dibromoneopentyl glycol, castor oil, trimethylolpropane, trimethylolethane, pentaerythritol, sorbitol or glycerol, or alkoxylated glycerol or alkoxylated trimethylolpropane;

[0124] - Hydrogenated bisphenol A, F or A / F liquid resin, or glycidylated product of hydrogenated bisphenol A, F or A / F;

[0125] N-glycidyl derivatives of amides or heterocyclic nitrogen bases, such as triglycidyl cyanurate or triglycidyl isocyanurate, or products of the reaction of epichlorohydrin with hydantoin;

[0126] - Epoxy resins obtained by oxidation of olefins, particularly vinylhexene, dicyclopentadiene, cyclohexadiene, cyclododecadiene, cyclododecadiene, isoprene, 1,5-hexadiene, butadiene, polybutadiene, or divinylbenzene.

[0127] Bisphenol-based liquid epoxy resins are preferred.

[0128] Particularly preferred are liquid epoxy resins based on bisphenol A, bisphenol F, or bisphenol A / F diglycidyl ethers, which are commercially available, for example, from Dow, Huntsman, or Momentive. These liquid epoxy resins readily achieve controllable viscosity and allow for high strength and resistance. Such liquid resins may also comprise a proportion of solid bisphenol A resin or phenolic varnish.

[0129] The weight ratio of the polymer containing silane groups to the liquid epoxy resin in the composition is preferably in the range of 20 / 80-70 / 30, especially 25 / 75-50 / 50. This type of composition has high strength along with good ductility.

[0130] The composition also preferably contains at least one polyamine, especially a polyamine having at least two amine hydrogens that are reactive to epoxy groups.

[0131] Suitable polyamines include the following:

[0132] - Aliphatic, cycloaliphatic or aryliphatic primary diamines, especially 2,2-dimethyl-1,3-propanediamine, 1,3-pentanediamine (DAMP), 1,5-pentanediamine, 1,5-diamino-2-methylpentane (MPMD), 2-butyl-2-ethyl-1,5-pentanediamine (C11-neo-diamine), 1,6-hexanediamine, 2,5-dimethyl-1,6-hexanediamine, 2,2(4),4-trimethylhexanediamine (TMD), 1,7-heptanediamine, 1,8-octanediamine, 1,9-nonanediamine, 1,10-decanediamine, undecane-1,11-diamine, dodecane-1,12-diamine, 1,2-, 1,3- or 1,4-diaminocyclohexane, 1,3-bis(amino)cyclohexane 1,4-Bis(aminomethyl)cyclohexane, 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane (isophorone diamine or IPDA), 2(4)-methyl-1,3-diaminocyclohexane, bis(4-aminocyclohexyl)methane, bis(4-amino-3-methylcyclohexyl)methane, bis(4-amino-3-ethylcyclohexyl)methane, bis(4-amino-3,5-dimethylcyclohexyl)methane, bis(4-amino-3-ethyl-5-methylcyclohexyl)methane, 2,5(2,6)-bis(aminomethyl)bicyclo[2.2.1]heptane (NBDA), 3(4),8(9)-bis(aminomethyl)tricyclo[5.2.1.0] 2,6 Decane, 1,4-diamino-2,2,6-trimethylcyclohexane (TMCDA), menthol-1,8-diamine, 1,3-bis(aminomethyl)benzene (MXDA) or 1,4-bis(aminomethyl)benzene;

[0133] - Aliphatic primary diamines or triamines containing ether groups, especially 3,6-dioxaoctane-1,8-diamine, 4,7-dioxadecane-1,10-diamine, 4,7-dioxadecane-2,9-diamine, 4,9-dioxadodecane-1,12-diamine, 5,8-dioxadodecane-3,10-diamine, 4,7,10-trioxatridecane-1,13-diamine or higher oligomers of these diamines, bis(3-aminopropyl)polytetrahydrofuran or other polytetrahydrofuran diamines, 3,9-bis(3-aminopropyl)-2,4,8,10-tetraoxaspiro[5.5]undecane, cyclic aliphatic diamines containing propoxylated and subsequently amination-substituted ether groups from 1,4-dihydroxymethylcyclohexane, can be particularly used as The special RFD-270 (from Huntsman) is obtained, or polyoxyalkylene diamine or polyoxyalkylene triamine, especially D-230 D-400 D-2000 EDR-104 EDR-148 EDR-176 T-403, T-3000 T-5000 (all from Huntsman), or the corresponding amines from BASF or Nitroil;

[0134] - Polyamines containing a secondary amine group and having two primary amine groups, such in particular 3-(2-aminoethyl)aminopropylamine, bis(hexamethylene)triamine (BHMT), diethylenetriamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TEPA), pentaethylenehexamine (PEHA), or higher analogues of linear polyethyleneamines, dipropylenetriamine (DPTA), N-(2-aminoethyl)-1,3-propanediamine (N3-amine) N,N'-bis(3-aminopropyl)ethylenediamine (N4-amine), N,N'-bis(3-aminopropyl)-1,4-diaminobutane, N5-(3-aminopropyl)-2-methyl-1,5-pentanediamine, N3-(3-aminopentyl)-1,3-pentanediamine, N5-(3-amino-1-ethylpropyl)-2-methyl-1,5-pentanediamine or N,N'-bis(3-amino-1-ethylpropyl)-2-methyl-1,5-pentanediamine;

[0135] - Polyamines containing tertiary amine groups, such as, in particular, 2-aminoethylpiperazine, 3-dimethylaminopropylamine (DMAPA), N,N-dimethylbis(1,3-propylidene)triamine (DMAPAPA), N,N'-bis(aminoethyl)piperazine, N,N'-bis(aminopropyl)piperazine, N,N-bis(3-aminopropyl)methylamine, and N,N-bis(3-aminopropyl)ethylamine;

[0136] - Aliphatic, cycloaliphatic or aryliphatic primary triamines, especially 4-aminomethyl-1,8-octanediamine, 1,3,5-tris(aminomethyl)benzene, 1,3,5-tris(aminomethyl)cyclohexane, tris(2-aminoethyl)amine, tris(2-aminopropyl)amine or tris(3-aminopropyl)amine; or

[0137] - Diamines having one primary amino group and one secondary amino group, especially products of the reductive alkylation of primary aliphatic polyamines with aldehydes or ketones, such as, in particular, N-benzyl-1,2-ethylenediamine, N-benzyl-1,2-propanediamine, N-benzyl-1,3-bis(aminomethyl)benzene, N-2-ethylhexyl-1,3-bis(aminomethyl)benzene, N-(2-phenethyl)-1,3-bis(aminomethyl)benzene (a component of styrene-modified 1,3-bis(aminomethyl)benzene, which can be used as...) 240 (obtained from Mitsubishi Gas Chemical); or

[0138] - The described amine or small amine, such as, in particular, 1,2-ethylenediamine or 1,2-propanediamine, adducts with monoepoxides or diepoxides, especially with tolyl glycidyl ether or bisphenol A-diglycidyl ether; or

[0139] - Polyamide amines, especially mono- or polycarboxylic acids, or their esters or anhydrides, especially dimer fatty acids, react with polyamines (especially polyalkylene amines such as DETA or TETA) in stoichiometric excess; or

[0140] - Mannich bases, especially phenolic amines, are the reaction products of phenols (especially cashew phenol) with aldehydes (especially formaldehyde) and polyamines.

[0141] Aliphatic, cyclic aliphatic, or aryl aliphatic polyamines are preferred.

[0142] Preferred polyamines are selected from the following: MPMD, TMD, 1,2-diaminocyclohexane, 1,3-diaminocyclohexane, 1,4-diaminocyclohexane, 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, IPDA, 2(4)-methyl-1,3-diaminocyclohexane, bis(4-aminocyclohexyl)methane, NBDA, MXDA, average molecular weight M n Poly(propylene oxide) diamine and poly(propylene oxide) triamine, BHMT, TETA, TEPA, N4 amine, DMAPAPA, N-benzyl-1,2-ethylenediamine, N-benzyl-1,2-propanediamine, N-benzyl-1,3-bis(aminomethyl)benzene, N-(2-phenylethyl)-1,3-bis(aminomethyl)benzene and MPMD or 1,2-propanediamine adducts with tolyl glycidyl ether in the range of 200-500 g / mol.

[0143] 1,2-Diaminocyclohexane is particularly preferred. This produces exceptionally high strength.

[0144] Among them, those with an average molecular weight M are particularly preferred. n Polyoxypropylene diamine or triamine in the range of 200-500 g / mol, especially D-230 D-400 or T-403. This produces an exceptionally high elongation.

[0145] Of particular preference are adducts of 1,2-propanediamine with tolyl glycidyl ether, especially o-tolyl glycidyl ether, wherein the adduct is preferably formed by an excess of 1,2-propanediamine relative to tolyl glycidyl ether, and the unadducted 1,2-propanediamine is removed by distillation after the reaction. This even produces a glossy surface under humid conditions.

[0146] A mixture of two or more polyamines can be used advantageously. A mixture comprising at least one polyoxypropylene diamine or triamine and at least one other polyamine is preferred.

[0147] The polyamine or mixture of two or more polyamines is preferably present in such an amount that the ratio of the number of amine hydrogens to the number of epoxy groups is in the range of 0.5 / 1 to 1.5 / 1, especially 0.8 / 1 to 1.2 / 1.

[0148] In a preferred embodiment, the composition of the present invention comprising at least one liquid epoxy resin and at least one polyamine is a two-component composition comprising first and second components that are manufactured, packaged, and stored separately from each other. More specifically, the polyamine is not present in the same component as the liquid epoxy resin.

[0149] In this case, it is preferred that 30-70% by weight, especially 40-60% by weight, of acetylene black in the first component and 70-30% by weight, especially 60-40% by weight, of acetylene black in the second component, based on the total weight of acetylene black in the composition.

[0150] In a preferred embodiment of the invention, the composition comprises a first component, the first component comprising...

[0151] - At least one polymer containing a silane group, as described above, and

[0152] - At least one liquid epoxy resin

[0153] The second component, the second component comprising

[0154] - At least one polyamine, especially an amine hydrogen having at least three reactive epoxy groups.

[0155] In another preferred embodiment of the invention, the composition comprises a first component, the first component comprising...

[0156] - At least one polymer containing a silane group, as described above, and

[0157] - at least one polyamine, particularly an amine hydrogen having at least three reactive epoxy groups, and a second component, the second component comprising

[0158] - At least one liquid epoxy resin.

[0159] In both implementations, the components are individually storage stable if moisture is excluded. When the two components are mixed, the primary and / or secondary amines react with the present epoxy groups. When the silanes come into contact with water, they react with the released hydroxide ions.

[0160] The compositions of the present invention preferably further comprise at least one additional component selected from aminosilanes, desiccants, accelerators, water, other fillers, and plasticizers. This also applies to compositions with and without liquid epoxy resins and polyamines.

[0161] Suitable aminosilanes, especially 3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-N'-[3-(trimethoxysilyl)propyl]ethylenediamine and their analogues using ethoxy groups instead of methoxy groups on silicon.

[0162] When polyamines are present, aminosilanes are suitable to be in the same component as polyamines.

[0163] The composition preferably has an aminosilane content in the range of 0.1% to 5% by weight, particularly in the range of 0.2% to 2% by weight. Such a composition has particularly high strength.

[0164] Suitable desiccants include tetraethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, organosilanes having a functional group at the α-position of a silane, especially N-(methyldimethoxysilylmethyl)-O-methylcarbamate or (methacryloyloxymethyl)silane, methoxymethylsilane, orthoformate, and calcium oxide or molecular sieves.

[0165] The composition more preferably contains vinyltrimethoxysilane or vinyltriethoxysilane. Vinyltrimethoxysilane is preferred when the polymer containing silane groups has methoxysilane groups, and vinyltriethoxysilane is preferred when the polymer containing silane groups has ethoxysilane groups.

[0166] The desiccant is suitable to be present in the same component as the polymer containing silane groups.

[0167] Suitable promoters are especially those that promote the crosslinking of polymers containing silane groups. Metal catalysts and / or nitrogen-containing compounds are particularly suitable for this purpose.

[0168] Suitable metal catalysts are compounds of titanium, zirconium, aluminum, or tin, especially organotin compounds, organotitanates, organozinates, or organoaluminates. These metal catalysts particularly possess alkoxy groups, aminoalkoxy groups, sulfonate / salt groups, carboxyl groups, 1,3-diketoester / salt groups, 1,3-ketoester groups, dialkyl phosphate / salt groups, or dialkyl pyrophosphate / salt groups. Particularly suitable are: dibutyltin oxide, dibutyltin dichloride, dibutyltin diacetate, dibutyltin dilaurate, dibutyltin diacetylacetonate, dioctyltin oxide, dioctyltin dichloride, dioctyltin dilaurate, or dioctyltin diacetylacetonate and organotitanates or organozinates.

[0169] Suitable nitrogen compounds, especially amidines such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 6-dibutylamino-1,8-diazabicyclo[5.4.0]undec-7-ene, or guanidines such as tetramethylguanidine, 2-guanidinylbenzimidazole, acetylacetoneguanidine, or reaction products of carbodiimides with amines such as, in particular, polyetheramines or aminosilanes.

[0170] Suitable accelerators are also, in particular, substances that promote the reaction of epoxy groups with amino groups. For this purpose, acids or compounds that can be hydrolyzed to acids are particularly suitable, especially organic carboxylic acids such as salicylic acid, organic sulfonic acids such as p-toluenesulfonic acid, sulfonates, phosphoric acid, or nitrates such as, in particular, calcium nitrate, or tertiary amines such as, in particular, 1,4-diazabicyclo[2.2.2]octane, triethanolamine, imidazoles such as, in particular, N-methylimidazolium, N-vinylimidazolium or 1,2-dimethylimidazolium, recorded amidines or guanidines, phenols or Mannich bases such as, in particular, 2,4,6-tris(dimethylaminomethyl)phenol, or compounds having a thiol group.

[0171] The composition preferably contains at least one accelerator selected from the following: dialkyltin compounds, organotitanates, amidines, guanidines, acids, calcium nitrates, and Mannich bases.

[0172] More preferably, the composition comprises 2,4,6-tris(dimethylaminomethyl)phenol and at least one additional accelerator.

[0173] In a preferred embodiment of the invention, the composition comprises water or a water-releasing substance. This type of composition has the advantage that the water required for the crosslinking of the silane groups requires little or no absorption from the environment.

[0174] The composition preferably contains a total of up to 5% by weight, especially up to 2% by weight, of free or releasable water.

[0175] Free water is not suitable for use in the same composition as polymers containing silane groups.

[0176] Other suitable fillers include, in particular, ground or precipitated calcium carbonate, optionally coated with fatty acids, especially stearates; barite; quartz powder; quartz sand; dolomite; wollastonite; calcined kaolin; flake silicates such as mica or talc; zeolite; aluminum hydroxide; magnesium hydroxide; silica, including finely crushed silica from pyrolysis processes; cement; gypsum; fly ash; other industrially produced carbon black; graphite; metal powders such as aluminum, copper, iron, silver, or steel powder; PVC powder; or lightweight fillers such as hollow glass beads or inflated plastic balls (microspheres), especially suitable for… The trademark name is of a type obtained (from AkzoNobel). Other industrially produced carbon blacks that can be used as other fillers are chemically and / or physically different from the acetylene black used according to the present invention as described above.

[0177] Calcium carbonate, calcined kaolin, and / or highly dispersed silica are preferred as other fillers.

[0178] Suitable plasticizers, especially carboxylic acid esters, such as phthalates, particularly diisononyl phthalate (DINP), diisodecyl phthalate (DIDP), or di(2-propylheptyl) phthalate (DPHP), hydrogenated phthalates or cyclohexane-1,2-dicarboxylate esters, especially hydrogenated diisononyl phthalate or diisononyl cyclohexane-1,2-dicarboxylate (DINCH), terephthalates, especially bis(2-ethylhexyl) terephthalate (DOTP) or diisononyl terephthalate (DINT), hydrogenated terephthalates or cyclohexane-1,4-dicarboxylate esters, especially hydrogenated bis(2-ethylhexyl) terephthalate. Plasticizers containing polyether structures, especially polyoxypropylene monools, diols, or triols containing block hydroxyl groups, particularly in the form of acetate groups, organophosphates or sulfonates, polybutene, polyisobutylene or plasticizers derived from natural fats or oils, especially epoxidized soybean oil or linseed oil.

[0179] Preferred plasticizers are phthalates, ethylene glycol esters, or plasticizers with a polyether structure.

[0180] The compositions of the present invention may contain other additives, especially

[0181] - Other crosslinking agents, especially additional silanes such as epoxysilanes or mercaptosilanes, or compounds with mercapto groups such as thiol-terminated polysulfide polymers or thiol-terminated polyoxyalkylene ethers.

[0182] - Solvent or diluent;

[0183] -Inorganic or organic pigments, especially titanium dioxide, chromium oxide or iron oxide;

[0184] -dye;

[0185] - Rheology modifiers, especially thickeners, particularly layered silicates such as bentonite, castor oil derivatives, hydrogenated castor oil, polyamides, polyurethanes, urea compounds, polyvinyl chloride, pyrolytic silica, cellulose ethers or hydrophobically modified polyoxyethylene.

[0186] - Natural resins, fats, or oils, such as rosin, shellac, linseed oil, castor oil, or soybean oil;

[0187] - Non-reactive polymers, especially homopolymers or copolymers of unsaturated monomers, said monomers being particularly derived from the group comprising: ethylene, propylene, butene, isobutylene, isoprene, vinyl acetate or (meth)acrylate, especially polyethylene (PE), polypropylene (PP), polyisobutylene, ethylene / vinyl acetate copolymer (EVA) or atactic poly-α-olefin (APAO).

[0188] - Fibers, especially glass fibers, carbon fibers, metal fibers, ceramic fibers, polymer fibers such as polyamide fibers or polyethylene fibers, or natural fibers such as wool, cellulose, hemp or sisal;

[0189] - Nanofillers such as graphene or carbon nanotubes;

[0190] - Flame retardants, especially the aluminum hydroxide or magnesium hydroxide fillers already mentioned, and especially organophosphates, such as triethyl phosphate, tricresyl phosphate, triphenyl phosphate, diphenyltoluene phosphate, isodecanyl diphenyl phosphate, tri(1,3-dichloro-2-propyl) phosphate, tri(2-chloroethyl) phosphate, tri(2-ethylhexyl) phosphate, tri(chloroisopropyl) phosphate, tri(chloropropyl) phosphate, isopropylated triphenyl phosphate, mono-, bis-, or tri(isopropylphenyl) phosphates with different degrees of isopropylation, resorcinol bis(diphenyl phosphate), bisphenol A bis(diphenyl phosphate), or ammonium polyphosphate;

[0191] - Additives, especially emulsifiers, wetting agents, leveling agents, defoamers, degassing agents, stabilizers or biocides that resist oxidation, heat, light or UV radiation.

[0192] It is desirable to chemically or physically dry certain components before mixing them into the composition, especially if they are stored with polymers containing silane groups.

[0193] Preferably, the composition of the present invention contains very little solvent. It particularly contains less than 5% by weight, preferably less than 2.5% by weight, of solvent. Most preferably, it is substantially solvent-free.

[0194] As a general rule, the compositions of the present invention preferably have a polymer content of 8% to 65% by weight, especially 12% to 60% by weight, in the range of silane groups.

[0195] The first particularly advantageous composition comprises the following components in the following proportions:

[0196] -12% by weight to 60% by weight of polymers containing silane groups,

[0197] -5% to 20% by weight of acetylene black,

[0198] -0% to 45% by weight, preferably 1% to 40% by weight, and especially 5% to 30% by weight of other fillers.

[0199] And other optional ingredients, in each case, weight % based on the total composition.

[0200] The second particularly advantageous composition comprises the components in the following proportions:

[0201] -12% by weight to 60% by weight of polymers containing silane groups,

[0202] -5% to 20% by weight of acetylene black,

[0203] -5% to 20% by weight of other fillers, especially calcium carbonate,

[0204] -0% to 5% by weight, preferably 0.5% to 3% by weight, especially 1% to 3% by weight of aminosilane,

[0205] -0 to 5% by weight, preferably 0.5% to 3% by weight, especially 1% to 3% by weight of desiccant, particularly vinyltrimethoxysilane or vinyltriethoxysilane,

[0206] And other optional ingredients, in each case, weight % based on the total composition.

[0207] The first two particularly advantageous compositions are preferably produced and used as single-component compositions. The first two compositions preferably do not contain liquid epoxy resin.

[0208] The first two particularly advantageous compositions are water-curing compositions that cure especially in the presence of water, particularly atmospheric moisture.

[0209] Therefore, it is preferable to produce such compositions and store them with moisture removed. Typically, the composition is storage stable, meaning it can be stored for several months to a year or longer in suitable packaging or equipment such as drums, roll-on / roll-off boxes, bags, cans, cylinders, or tubes with moisture removed, and its application properties or properties after curing remain unchanged to the extent relevant to its use. Storage stability is usually determined by measuring viscosity or extrusion force.

[0210] Other advantageous compositions also include a liquid epoxy resin and a polyamine, and preferably have the following components:

[0211] The composition comprising the additional liquid epoxy resin and polyamine preferably has a polymer containing silane groups in the range of 10% to 50% by weight, particularly 12% to 40% by weight. In the case of a two-component system, the content is based on the total mass of the two components.

[0212] Compositions comprising additional liquid epoxy resin and polyamine preferably have a liquid epoxy resin content in the range of 10% to 60% by weight, particularly 20% to 50% by weight. In the case of a two-component system, the content is based on the total mass of the two components.

[0213] The composition comprising additional liquid epoxy resin and polyamine preferably has a total content of liquid epoxy resin and reactive diluent containing epoxy groups in the range of 20%-70% by weight, especially 25%-65% by weight.

[0214] The third particularly advantageous composition comprises:

[0215] -12% by weight to 40% by weight of polymers containing silane groups,

[0216] -5% to 20% by weight of acetylene black,

[0217] -20% to 50% by weight of liquid epoxy resin,

[0218] -0% to 20% by weight, preferably 1% to 15% by weight, of reactive diluent containing epoxy groups.

[0219] -5% to 40% by weight of polyamines,

[0220] -0% to 45% by weight, preferably 1% to 40% by weight of other fillers.

[0221] And other optional ingredients, in each case, weight % based on the total composition.

[0222] Preferably, the composition comprises a liquid epoxy resin and a polyamine and is used as a two-component composition. The first and second components of the composition are manufactured separately and stored in a moisture-proof container. Suitable containers include, in particular, drums, roll-on / roll-off boxes, bags, barrels, cans, cylinders, or tubes.

[0223] To use a two-component composition, the two components are mixed together shortly before or during application. The mixing ratio is preferably chosen such that reactive groups and epoxy groups are present in a suitable ratio, as described above. The mixing ratio is typically in the range of 1:10 to 10:1 by weight.

[0224] The two components should be mixed using a suitable method; mixing can be done continuously or in batches, using a static mixer or with the aid of a dynamic mixer. If mixing is done before application, care must be taken to ensure that application occurs within the pot life of the composition, as otherwise damage may occur, such as delayed or incomplete adhesion to the substrate or premature gelation.

[0225] "Positive application period" refers to the time after the components have been mixed to when the composition should be applied.

[0226] The components are preferably mixed at ambient temperature, which is typically in the range of about 0-50°C, preferably about 5 to 35°C.

[0227] Curing begins as the two components are mixed through a chemical reaction. The epoxy group reacts with amine hydrogen, and the silane group undergoes hydrolysis to release hydroxyl groups, forming silanol groups (Si-OH groups), which then form siloxane groups (Si-O-Si groups) through a subsequent condensation reaction. These and possibly additional reactions result in the composition curing to form a cross-linked polymer. If the water from the hydrolysis of the silane groups is not already present in the composition, it can originate from the air (atmospheric humidity) or from the substrate, or the composition can come into contact with the aqueous component, for example, through coating, spraying, or incorporation.

[0228] Curing occurs particularly at temperatures ranging from 0 to 150°C. It can also occur especially at ambient temperature, in which case it typically lasts from several days to several weeks until substantially complete under the conditions at that time. In some cases, it is advantageous to further cure the composition, which has already partially cured at ambient temperature, at a higher temperature.

[0229] The described composition is applied to at least one substrate, the following substrates being particularly suitable:

[0230] - Metals or alloys, such as aluminum, iron, steel, copper, and other non-ferrous metals, including surface-treated metals or alloys, such as zinc-plated or chromium-plated metals;

[0231] - Concrete, mortar, cementitious plaster, fiber cement, brick, tile, plaster and natural stone such as granite or marble;

[0232] -Asphalt or pitch;

[0233] - Coated or painted substrates, especially painted nonwoven fabrics, coated concrete, powder-coated metals or alloys, or painted metal sheets.

[0234] - Repair or leveling materials based on PCC (polymer modified cement mortar) or ECC (epoxy resin modified cement mortar);

[0235] - Leather, fabric, paper, wood, wood-based materials bonded with resins (such as phenolic resins, melamine resins, or epoxy resins), resin-fabric composites, or other so-called polymer composites;

[0236] - Plastics, such as rigid and flexible PVC, polycarbonate, polystyrene, polyester, polyamide, PMMA, ABS, SAN, epoxy resin, phenolic resin, PUR, POM, TPO, PE, PP, EPM or EPDM, in each case are untreated or surface-treated, for example by plasma, corona or flame treatment.

[0237] - Fiber-reinforced plastics, such as carbon fiber reinforced plastics (CFRP), glass fiber reinforced plastics (GFRP), and sheet molding compounds (SMC);

[0238] - Glass or glass-ceramic;

[0239] - Insulating foam, especially made of EPS, XPS, PUR, PIR, rock wool, glass wool or foamed glass.

[0240] If necessary, the substrate may be pretreated before application, especially by physical and / or chemical cleaning methods or by applying an activator or primer.

[0241] The cured composition is obtained by curing the composition.

[0242] The cured composition has high strength, high ductility and high tear resistance.

[0243] The composition is preferably used as an adhesive, sealant, coating or casting material, especially on at least one metal, such as steel or aluminum, preferably aluminum.

[0244] When used on at least one metal, this has the advantage that the metal is protected from corrosion by the composition. This means that even in the event of exposure to, for example, salt water, the adhesion is not weakened due to metal corrosion. In particular, unanodized aluminum can be bonded without the use of a primer, provided that the adhesion is not weakened by corrosion even in the event of exposure to salt water.

[0245] The composition is preferably used as a viscoelastic adhesive. In this case, after the components are mixed, it typically has a liquid or paste-like consistency and structural viscous properties. Upon application, the mixed adhesive is applied to at least one of the substrates to be bonded within its pot life, and the substrates bond together within the adhesive's open time to form an adhesive bond.

[0246] The "open time" of an adhesive refers to the maximum length of time between the application of the adhesive and the bonding of the parts to be bonded, during which cohesive bonding can still be formed.

[0247] The mixed adhesive is applied, especially by means of brushes, rollers, scrapers, trowels, or from tubes, cylinders, or metering devices.

[0248] Adhesives are particularly suitable for use in the construction industry or for bonding components in the manufacturing industry.

[0249] Therefore, the present invention also provides an adhesive method, characterized in that a composition, or a mixture thereof in the case of a two-component composition, is applied to at least one substrate to be bonded during its pot life, and the substrates are bonded together to form an adhesive during an open time, after which the composition is cured. Here, the at least one substrate is preferably a metal, especially aluminum or steel, more preferably aluminum.

[0250] The composition is also preferably used as a coating, especially as a coating for metals such as steel or aluminum, wherein the composition protects the metal from corrosion.

[0251] The composition is preferably also used as a filler for cavities such as cracks, gaps, or drill holes, wherein the mixed composition is filled or injected into the cavity, and after curing, it fills the cavity and viscoelastically bonds the sides of the cavity together, thereby producing excellent adhesion even on a wet substrate. Therefore, damaged surfaces or curbs, edges, or boundaries of roads, plazas, steps, walls, or other building structures can be permanently repaired in a simple manner, and the repaired location remains very stable even under severe stress.

[0252] When filling cavities, anchors such as reinforcing rods, threaded rods, or bolts can be introduced into the cavities if necessary.

[0253] Therefore, the present invention also provides a method for coating a substrate or filling cavities, especially cracks or gaps, characterized in that the composition, or in the case of a two-component composition, is applied to the substrate or used to fill cavities within its pot life and cured in situ. When filling cavities, anchors may optionally be inserted into the cavities while the composition remains free-flowing.

[0254] The application and curing of the composition, or the bonding method, or the coating of a substrate, or the filling of a cavity, provides an article. The article can be a building structure or part thereof, particularly roads, plazas, steps, curbs, edges, boundaries, or walls, or it can be an industrial product or a consumer product, particularly a motor vehicle or part thereof, especially a battery box for a motor vehicle.

[0255] The present invention therefore also provides articles obtained by the described uses or by the described methods of bonding or filling cavities.

[0256] The compositions of the present invention possess advantageous properties, particularly good storage stability, rapid curing (even under wet or humid conditions), surprisingly high strength along with high ductility, high tear resistance, high stability, and high adhesion to a wide range of substrates, wherein the compositions protect metals such as steel or aluminum from corrosion when used thereon. The compositions thus enable reliable adhesion to untreated aluminum under corrosive conditions.

[0257] Another aspect of the invention relates to the use of acetylene black as a filler, particularly in adhesives, of compositions comprising at least one polymer containing a silane group. As described above, acetylene black is particularly advantageous compared to other carbon blacks.

[0258] Acetylene black is particularly used to achieve thixotropy or improve the thixotropy of a composition.

[0259] The present invention also relates to the use of acetylene black for increasing the viscosity of compositions comprising at least one silane-containing group. These are, in particular, compositions as described above, especially those according to the three embodiments described as particularly preferred. Acetylene black preferably has the properties described above.

[0260] Brief description of the attached diagram

[0261] Figure 1 Images of adhesive beads produced by dispersing the components of the two-component compositions of the present invention (L2A, L3A, L2B, and L3B) containing acetylene black are shown. Images of adhesive beads from non-two-component compositions of the present invention (L1A and L1B) are shown for comparison.

[0262] Working Example

[0263] The following describes working examples, the purpose of which is to further illustrate the invention. Of course, the invention is not limited to these described working examples.

[0264] "Standard climatic conditions" ("SCC") refer to a temperature of 23±1℃ and a relative humidity of 50±5%.

[0265] Unless otherwise stated, the chemicals used are from Sigma-Aldrich Chemie GmbH.

[0266] Comparative examples are determined by (Ref.).

[0267] Preparation of diethyl N-(3-trimethoxysilylpropyl)aminosuccinate

[0268] The following is the preparation of diethyl N-(3-trimethoxysilylpropyl)aminosuccinate: Initially, 51.0 g of 3-aminopropyltrimethoxysilane was added. A-1110 (Momentive Performance Materials Inc., USA). Add 49.0 g of diethyl maleate (Fluka Chemie GmbH, Switzerland) slowly with vigorous stirring at room temperature and stir the mixture at room temperature for 2 hours.

[0269] Preparation of the first polymer STP1 containing silane groups

[0270] After removing the moisture, use continuous stirring to mix 1000g of... 12200 polyols (from Covestro; low monool polyoxypropylene glycol, OH value 11.0 mg KOH / g, water content approximately 0.02% by weight), 43.6 g of isophorone diisocyanate ( IPDI (from Evonik Industries), 126.4 g of diisodecyl phthalate, and 0.12 g of dibutyltin dilaurate were heated to 90°C and maintained at this temperature until the free isocyanate group content determined by titration reached 0.63% by weight. Then, 62.3 g of N-(3-trimethoxysilylpropyl)aminosuccinate diethyl ester was added, and the mixture was stirred at 90°C until free isocyanate was no longer detectable by FT-IR spectroscopy. The silane-functionalized polymer was cooled to room temperature and stored after removing moisture.

[0271] Preparation of the second polymer STP2 containing silane groups

[0272] 400g of polyoxypropylene glycol (POP) was processed at 80°C using a known process. 4200, from Covestro AG; OH value 28.5 mg KOH / g) and 52 g of diphenylmethane-4,4'-diisocyanate ( 44MC L (from Covestro AG) was reacted to produce an NCO-terminated polymer that was liquid at room temperature and had an isocyanate group content of 1.85 wt%. Then, 72 g of N-(3-trimethoxysilylpropyl)aminosuccinate diethyl ester was added and the mixture was stirred at 90 °C until free isocyanate was no longer detectable by FT-IR spectroscopy. The silane-functionalized polymer was cooled to room temperature and stored with moisture removed.

[0273] Carbon black used

[0274] Use the carbon black shown in Table 1 below:

[0275] Table 1: Carbon Black Used

[0276]

[0277] 1) Furnace black (available from Orion Engineered Carbons LLC)

[0278] 2) Acetylene black (available from Orion Engineered Carbons LLC)

[0279] + It has a dew point of 12°C and a temperature of 23°C in the air.

[0280] Printex 60 carbon black is dried at 110°C for 12 hours before use, then cooled to RT under a nitrogen atmosphere and used directly in the composition. Other types of carbon black can be used directly without the drying step.

[0281] Production of single-component compositions:

[0282] For each composition Z1-Z4, the components specified in Table 1 are mixed in the specified amounts (parts by weight) using a centrifugal mixer. TM DAC 150 (FlackTek Inc.) is mixed and stored under conditions that exclude moisture.

[0283] Examples Z1 to Z3 are embodiments of the present invention, wherein the acetylene black (Y50A, YS, or Y200) of the present invention is used. Example Z4 is a comparative example using furnace black (Printex 60).

[0284] Table 2: Single-component STP compositions

[0285]

[0286] 1) Plasticizer, diisodecyl phthalate (from Exxon Mobil)

[0287] 2) Socal U1S2 (Solvay)

[0288] 3) N-(β-aminoethyl)-γ-aminopropyltrimethoxysilane (from Momentive)

[0289] 4) Jayflex DIDP 10 wt% dibutyltin dilaurate (DBTL) solution

[0290] To determine the pot life, stir 50g of the freshly mixed composition in a 500ml beaker using a spatula at 5-minute intervals until it feels as if the composition has thickened to the point where it no longer has good processability.

[0291] To determine the mechanical properties, the mixed composition was poured onto a PTFE-coated film to produce a 2 mm thick film, which was then stored under standard climatic conditions. After one day, numerous dumbbell-shaped test specimens with a length of 75 mm, a bar length of 30 mm, and a bar width of 4 mm were punched out of the film and stored under standard climatic conditions for another 6 days. The tensile strength (breaking force), elongation at break, and modulus of elasticity (Young's modulus) of these specimens were then determined at a strain rate of 2 mm / min, as described in DIN EN 53504. Similarly, numerous test specimens were punched out and stored for tear resistance determination, and tested at a strain rate of 500 mm / min according to DIN ISO 34.

[0292] The extrusion force was measured through a 5 mm diameter opening in the barrel after one day at room temperature.

[0293] Adhesive-based prism beads (approximately 10 mm wide; approximately 20 mm high, see [reference]). Figure 1 The thixotropic stability of the adhesive bead is visually evaluated for its sag resistance. The test examines whether the composition can be easily applied and whether the adhesive bead retains its prismatic shape after application. If so, it is classified as stable thixotropy. Other cases—where the adhesive bead flows after application—are referred to as unstable thixotropy.

[0294] These results are recorded in Table 3.

[0295] Table 3: Properties of the Composition

[0296]

[0297] The main differences in the compositions lie in the thixotropic behavior and extrusion force of the different types of carbon black. However, the comparative material (Example Z4) shows that, in contrast to the self-flowing parallel, acetylene black (Examples Z1-Z3) achieves stable thixotropy and better application properties at sufficiently low extrusion forces.

[0298] Compositions Z5-Z10 were also produced. For this, the components specified in Table 4 were mixed in the specified amounts (parts by weight) using a centrifugal mixer (SpeedMixer). TM DAC 150 (FlackTek Inc.) is mixed and stored under conditions that exclude moisture.

[0299] Examples Z5 to Z10 are embodiments of the present invention, wherein a larger proportion of the acetylene black (Y50A, YS or Y200) of the present invention is used.

[0300] Table 4: Single-component STP compositions with increased carbon black content

[0301]

[0302] 1) Plasticizer, diisodecyl phthalate (from Exxon Mobil)

[0303] 2) Socal U1S2 (Solvay)

[0304] 3) N-(β-aminoethyl)-γ-aminopropyltrimethoxysilane (from Momentive)

[0305] 4) Jayflex DIDP 10 wt% dibutyltin dilaurate (DBTL) solution

[0306] Based on the descriptions of compositions Z1-Z4, the properties of compositions Z5-Z10 were determined. The results are recorded in Table 5.

[0307] Table 5: Properties of the Composition

[0308]

[0309]

[0310] Using carbon black Y50A (Examples Z5 and Z8) and Y200 (Examples Z6 and Z9), a filler level of 15% by weight can be achieved with relatively low extrusion force. The best overall performance was observed using Y50A type carbon black.

[0311] Additionally, the adhesion properties of compositions Z1-Z10 were tested on the following substrates: AlMgSi1, anodized aluminum, V2A type stainless steel, fiber-reinforced plastics, and glass ceramics. For all types of carbon black, the adhesion properties were tested with and without the use of adhesion promoters. In the case of Aktivator 205, comparable adhesive properties are achieved. Therefore, acetylene black has no adverse effect on adhesiveness.

[0312] Production of two-component compositions:

[0313] For each composition L1-L3, the components of component 1 specified in Table 6 are mixed in the specified amounts (parts by weight) using a centrifugal mixer. TM DAC 150 (FlackTek Inc.) is mixed and stored under conditions that exclude moisture.

[0314] The same processing and storage are performed on the components specified in Table 6 for component 2.

[0315] The two components of each composition are then processed into a homogeneous liquid using a centrifugal mixer at a specified mixing ratio (0.6 / 1 by weight) and tested immediately.

[0316] Table 6: Two-component STP epoxy compositions

[0317]

[0318]

[0319] 1) DCH-99 (from Invista)

[0320] 2) 3-Aminopropyltrimethoxysilane (from Momentive)

[0321] 3) 2,4,6-Tris(dimethylaminomethyl)phenol (from Evonik)

[0322] 4) Bis(2,2,6,6-tetramethyl-4-piperidinyl) sebacate (from BASF)

[0323] 5) 3-(3,5-di-tert-butyl-4-hydroxyphenyl)octadecyl propionate (from BASF)

[0324] 6) GY 250 (from Huntsman)

[0325] 7) DY-H (from Huntsman)

[0326] 8) Disponil LS 500 (from BASF)

[0327] 9) The ratio of component 1 to component 2 by weight

[0328] Based on the descriptions of compositions Z1-Z4, the properties of compositions L1, L2, and L3 were determined.

[0329] Viscosity was measured on a temperature-controlled Rheotec RC30 parallel plate viscometer (plate diameter 25 mm, distance 1 mm, shear rate 10-100 s). -1 ).

[0330] The results are recorded in Table 7.

[0331] Table 7: Properties of Two-Component Compositions

[0332]

[0333] Figure 1 Images show adhesive beads produced by dispensing compositions L1A, L2A, L3A, L1B, L2B, and L3B. However, adhesive beads from compositions L2A, L3A, L2B, and L3B containing acetylene black retain their prismatic shape, while adhesive beads from compositions L1A and L1B containing furnace black flow.

[0334] In the case of acetylene black, mechanical properties (tensile strength, elongation at break, and tear resistance) are improved. Additionally, these types of carbon black can be used to produce stable thixotropy (see [link to relevant documentation]). Figure 1 The latter is also evident from the measured shear stress and viscosity results. Here, again, the fact that no drying process is required for acetylene black is a significant advantage.

[0335] When using conventional carbon black, it is not possible to obtain thixotropically stable component A, even when the amount of carbon black is increased.

[0336] Additionally, the adhesive properties of compositions L1, L2, and L3 were tested on the following substrates: AlMgSi1, anodized aluminum, V2A type stainless steel, fiber-reinforced plastics, and glass ceramics. For all types of carbon black, the adhesive properties were tested with and without the use of adhesion promoters (…). In the case of Aktivator 205, comparable adhesive properties are achieved. Therefore, acetylene black has no adverse effect on adhesiveness.

[0337] In summary, it was discovered that the use of acetylene black can achieve good thixotropy in STP epoxy formulations with low raw material levels. This is impossible to achieve using other types of carbon black in the same manner. In particular, thixotropic behavior can be achieved in amine and epoxide components. Mechanical properties are only slightly affected by this.

[0338] Similarly, acetylene black can provide STP formulations without pre-drying. When the proportion of carbon black is comparable, the mechanical properties of acetylene black are superior to those of other carbon blacks, and thixotropic behavior is achieved more effectively.

Claims

1. A composition comprising: - at least one silane group containing polymer, which is not a polydimethylsiloxane polymer, wherein the at least one silane group containing polymer has polyoxypropylene units and is obtained from the reaction of at least one isocyanate group containing polymer with at least one aminosilane, - at least one acetylene black, wherein the acetylene black has an oil absorption number (OAN) of > 200 ml / 100 g, wherein the acetylene black has a BET surface area of 30-100 m 2 / g.

2. The composition according to claim 1, wherein the acetylene black has an oil absorption number (OAN) of > 250 ml / 100 g.

3. The composition according to claim 1, wherein the acetylene black has an oil absorption number (OAN) of > 300 ml / 100 g.

4. The composition according to claim 1 or 2, wherein the acetylene black has a BET surface area of ​​50-90 m². 2 / g.

5. The composition according to claim 1 or 2, wherein the acetylene black has a BET surface area of ​​60-80 m². 2 / g.

6. The composition according to claim 1 or 2, wherein the acetylene black has a carbon content of > 98 wt.-%.

7. The composition according to claim 1 or 2, wherein the acetylene black has a carbon content of > 99 wt.-%.

8. The composition according to claim 1 or 2, wherein the acetylene black has a carbon content of > 99.5 wt.-%.

9. The composition according to claim 1 or 2, wherein the acetylene black has a dew point in air of 12°C and has an equilibrium moisture content of < 0.2 wt.-% at a temperature of 23°C.

10. The composition according to claim 1 or 2, wherein the acetylene black is present in an amount of 5 to 20 wt.-% based on the total weight of the composition.

11. The composition according to claim 1 or 2, wherein the acetylene black is present in an amount of 8 to 18 wt.-% based on the total weight of the composition.

12. The composition according to claim 1 or 2, wherein the acetylene black is present in an amount of 10 to 15 wt.-% based on the total weight of the composition.

13. The composition according to claim 1, wherein the isocyanate group containing polymer has an NCO content in the range of 0.25 wt.-% to 4 wt.-%.

14. The composition according to claim 1, wherein the isocyanate group containing polymer has an NCO content in the range of 0.3 wt.-% to 3.5 wt.-%.

15. The composition according to claim 1, wherein the aminosilane is N-(3- trimethoxysilylpropyl) diethylamino succinate, N-(3-dimethoxymethylsilylpropyl) diethylamino succinate or N-(3-triethoxysilylpropyl) diethylamino succinate.

16. The composition according to claim 1 or 2, wherein the silane group containing polymer has a silane group of formula (I) wherein n is 1 or 2 or 3; R 1 is a linear or branched, monovalent hydrocarbon group having 1 to 5 carbon atoms, R 2 is a linear or branched divalent hydrocarbon-based radical having from 1 to 12 carbon atoms and optionally having cyclic and / or aromatic moieties and optionally having one or more heteroatoms, X is O or S or NR 3 wherein R 3 is a hydrogen atom or a linear or branched hydrocarbon group having 1 to 20 carbon atoms, which optionally has a cyclic moiety and optionally has an alkoxysilyl group or an ether group or a carboxylate group.

17. The composition of claim 16, wherein R 2 is an amido, carbamate, or morpholino group.

18. The composition according to claim 1 or 2, wherein it further comprises at least one further component selected from the group consisting of aminosilane, a drying agent, an accelerator, water, a filler and a plasticizer.

19. The composition according to claim 1 or 2, further comprising: - at least one liquid epoxy resin, and - at least one polyamine.

20. The composition according to claim 19, wherein the polyamine has at least three amine hydrogens which are reactive towards epoxy groups.

21. The composition according to claim 19, wherein it comprises a first component and a second component which are produced, packaged and stored separately, wherein the polyamine is not in the same component as the liquid epoxy resin.

22. The composition according to claim 21, wherein 30 to 70 wt.-% of the acetylene black based on the total weight of the acetylene black in the composition is present in the first component and 70 to 30 wt.-% of the acetylene black is present in the second component.

23. The composition according to claim 22, wherein 40 to 60 wt.-% of the acetylene black based on the total weight of the acetylene black in the composition is present in the first component and 60 to 40 wt.-% of the acetylene black is present in the second component.

24. The composition according to claim 1, wherein the composition is a composition for use as an adhesive, a sealant, a coating or a casting compound.

25. Use of an acetylene black having an oil absorption number (OAN) of > 200 ml / 100 g for achieving thixotropy of a composition comprising at least one silane group containing polymer, which is not a polydimethylsiloxane polymer, and / or for increasing the viscosity of a composition comprising at least one silane group containing polymer, which is not a polydimethylsiloxane polymer, wherein the at least one silane group containing polymer has polyoxypropylene units and is obtained from the reaction of at least one isocyanate group containing polymer with at least one aminosilane.

26. The use according to claim 25, wherein the acetylene black is an acetylene black as described in any one of claims 1 to 24 and the composition is a composition according to any one of claims 1 to 24.

27. A method of bonding, characterized by The composition according to any one of claims 1 to 24 is applied to at least one substrate to be bonded within the pot life and the substrates are bonded within the open time to form a bonded body, after which the composition is cured.

28. An article obtained from the use according to claim 25 or the method according to claim 27.

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