WO2024251789A1 - Composition durcissable thermoconductrice - Google Patents

Composition durcissable thermoconductrice Download PDF

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Publication number
WO2024251789A1
WO2024251789A1 PCT/EP2024/065431 EP2024065431W WO2024251789A1 WO 2024251789 A1 WO2024251789 A1 WO 2024251789A1 EP 2024065431 W EP2024065431 W EP 2024065431W WO 2024251789 A1 WO2024251789 A1 WO 2024251789A1
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composition
component
curable composition
component curable
groups
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Davide BANDERA
David Hofstetter
Klaas Mennecke
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Sika Technology AG
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Sika Technology AG
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Priority to EP24729874.8A priority Critical patent/EP4724511A1/fr
Priority to CN202480025865.5A priority patent/CN120958055A/zh
Publication of WO2024251789A1 publication Critical patent/WO2024251789A1/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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C08G59/5026—Amines cycloaliphatic
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C08G59/5006—Amines aliphatic
    • C08G59/5013—Amines aliphatic containing more than seven carbon atoms, e.g. fatty amines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides
    • 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
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • 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
    • C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D171/02—Polyalkylene oxides
    • 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
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • 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
    • C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
    • C09J171/02—Polyalkylene oxides
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2227—Oxides; Hydroxides of metals of aluminium
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/001—Conductive additives

Definitions

  • the invention relates to multi-component compositions which are curable at room temperature and are based on a combination of silane group-containing polymer and epoxy resin, and their use as adhesives, sealants, coatings, gap fillers or potting resins.
  • Curable compositions based on polymers containing reactive groups play an important role in many industrial applications, for example as adhesives, sealants, coatings, or potting resins. Such compositions chemically cure to cross-linked plastics with a broad possible range of mechanical, chemical, and physical properties.
  • Such chemically curing compositions can be formulated as one-component, ready-to-use compositions by employing reactive polymers that only cure when exposed to external influences, such as heat or humidity, in order to ensure sufficient storage stability inside their package prior to use.
  • Another possibility is to use multi-component compositions (in most cases two-component compositions) that are mixed with each other right before or during application.
  • two-component curable compositions are for example two- component epoxy resin adhesives. These adhesives attain very high strengths but are normally not tough and elastic, instead being brittle and barely stretchable, and hence unsuitable for numerous applications within structural adhesive bonding or other industrial assembly operations.
  • curable materials based on silane-functional polymers are mostly one-component formulations which crosslink at room temperature by reaction with atmospheric moisture. They are notable for blister-free curing and for high adhesion forces but cure relatively slowly and are very limited in terms of maximum attainable strength. Oftentimes they also have low tear resistance, being therefore decidedly brittle. Furthermore, they are relatively unstable thermally. Hence, they are poorly suited to use as tough elastic adhesive or in thermally demanding applications. Also known are curable materials based on a combination of silane-functional polymers with epoxy resins, from EP 0 186 191 and EP 0 370 464, for example.
  • Such materials are commonly in two-component form and attain greater strength and toughness than those based on silane-functional polymers alone but are still in need of improvement in this regard.
  • Another example of such a composition is disclosed in CN 115 926 719 A.
  • two-component compositions based on silane-terminated polyurethane resins and epoxy resins are disclosed. More specifically, their first component contains, inter alia, 50-70 parts of silane-terminated polyurethane resin and 10-20 parts of a first flameretardant filler, for example alumina.
  • Their second component contains, inter alia, 40-60 parts epoxy resin and also 10-20 parts of a second flame-retardant filler, for example polyphosphate.
  • thermally conductive compositions are mainly limited to silicones and thus have limited applicability in automotive, especially electric vehicle, manufacturing.
  • thermally conductive compositions based on silane-functional polymers having high content of thermally conductive fillers have been developed. However, they are mechanically weak due to their low polymer content and can most suitably be used as gap fillers only.
  • epoxybased such highly filled, thermally conductive compositions have been developed, but they suffer from high viscosity and intrinsic brittleness, which makes their application cumbersome and reduces their suitability as potting resin or adhesive with exposure to vibrations or other mechanical impacts.
  • curable composition that exhibits low viscosity and pumpability and outstanding mechanical properties and thus is suitable as adhesive, gap filler, sealant, or potting resin especially for battery and electronics assembly and that furthermore possesses high thermal conductivity but at the same time does not interfere with coating or painting processes, in particular e-coat processes.
  • the present invention achieves these objects with the features of independent claim 1 .
  • the present invention relates in a first aspect to multi-component curable composition, comprising
  • liquid epoxy resin EP and said polyamine PA are not being present in the same component, and in that said organic polymer PO and said water are not present in the same component.
  • reactive silane group refers to a silyl group that is bonded to an organic radical and has one to three, especially two or three, hydrolyzable substituents or hydroxyl groups on the silicon atom. Particularly useful hydrolyzable substituents are alkoxy groups. These silane groups are also referred to as “alkoxysilane groups”. Reactive silane groups may also be in partly or fully hydrolyzed form, for example as silanols.
  • Hydrosilane “Hydroxysilane”, “isocyanatosilane”, “aminosilane” and “mercaptosilane” refer respectively to organoalkoxysilanes having one or more hydroxyl, isocyanato, amino or mercapto groups on the organic radical in addition to the silane group.
  • Organicfunctional compound refers to a compound that contains a functional group that is bound via a carbon atom.
  • aminofunctional compound is a compound having an aminoalkyl group.
  • Primary amino group refers to an NH2 group that is bonded to an organic radical
  • secondary amino group refers to an NH group that is bonded to two organic radicals which may also together be part of a ring
  • tertiary amino group refers to an N group that is bonded to three organic radicals, two or three of which together may also be part of one or more rings.
  • primary aminosilanes are aminosilanes comprising a primary amino group
  • secondary aminosilanes are aminosilanes comprising a secondary amino group. The latter also encompasses compounds having both a primary and a secondary amino group.
  • Polyoxyalkylene radical refers to a linear or branched hydrocarbyl radical which contains ether groups and contains more than two repeat units of the (O-R) type in succession, where R is a linear or branched alkylene radical, as for example from the polyaddition of ethylene oxide or 1 ,2-propylene oxide onto starter molecules having two active hydrogen atoms.
  • Substance names beginning with “poly”, such as polyol or polyisocyanate, refer to substances containing, in a formal sense, two or more of the functional groups that occur in their name per molecule.
  • organic polymer encompasses a collective of macromolecules that are chemically homogeneous but differ in relation to degree of polymerization, molar mass and chain length, which has been prepared by a poly reaction (polymerization, polyaddition, polycondensation) and has a majority of carbon atoms in the polymer backbone, and reaction products of such a collective of macromolecules.
  • Polymers having a polyorganosiloxane backbone commonly referred to as “silicones” are not organic polymers in the context of the present document.
  • polyether containing reactive silane groups also encompasses organic polymers which contain silane groups and which, in addition to polyether units, may also contain urethane groups, urea groups or thiourethane groups. Such polyethers containing reactive silane groups may also be referred to as “polyurethanes containing reactive silane groups”.
  • Molecular weight is understood in the present document to mean the molar mass (in grams per mole) of a molecule or part of a molecule, also referred to as “radical”.
  • the term “radical” is used in this document in a formal sense, meaning a molecular rest bound to an atom by a covalent bond, while the bond is formally “cut” to describe the molecular rest attached to it.
  • Molecular weight of polymers is understood as the average molecular weight of their chain length distribution.
  • Average molecular weight is understood herein to mean the number-average M n of an oligomeric or polymeric mixture of molecules or radicals, which is typically determined by means of gel permeation chromatography (GPC) against polystyrene as standard.
  • Weight percent or “percentage by weight”, and its abbreviation “wt.-%” refer to the weight percentage of a certain compound in a total composition, if not otherwise defined.
  • “Storage-stable” or “storable” refers to a substance or composition when it can be stored at room temperature in a suitable container over a prolonged period, typically at least 3 months up to 6 months or more, without any change in its application or use properties, especially in the viscosity and crosslinking rate, to a degree of relevance for the use thereof as a result of the storage.
  • Root temperature refers to a temperature of 23°C.
  • Thermal conductivity is defined as ability of material to transmit heat and it is measured in watts per metre-kelvin (W/(m-K)), herein denoted as “W/mK”. Thermal conductivity of materials disclosed in this document are measured according to ASTM D5470-06, if not otherwise specified.
  • a dotted line in the formulae in this document in each case represents the bond between a substituent and the corresponding molecular radical.
  • does not contain polydiorganosiloxanes means that no such compounds have been added during formulation of the composition. If traces of such species are unknowingly and/or unavoidably present, for example stemming from the synthesis of the silane-functional polymer or due to condensation reactions of silane-functional diorganosilane compounds possibly present in the composition, these are not considered as polydiorganosiloxanes in the meaning of this term.
  • the term “does not contain polydiorganosiloxanes” means that no silicone oils or reactive silicone polymers, in particular polydimethylsiloxanes, were added during formulation of the composition.
  • composition according to the present invention comprises at least one organic polymer PO containing alkoxysilane groups.
  • the composition comprises composition comprises between 3 wt.-% and 10 wt.-%, preferably between 3.5 wt.-% and 7.5 wt.-%, in particular between 4 wt.-% and 6 wt.-%, based on the total composition, of said organic polymer PO
  • the organic polymer PO containing alkoxysilane groups is in particular a polyurethane, polyolefin, polyester, polycarbonate, polyamide, poly(meth)acrylate or polyether or a mixed form of these polymers, each of which bears one or preferably more than one reactive alkoxysilane group.
  • the alkoxysilane groups may be in pendant positions in the chain or in terminal positions and are bonded to the organic polymer via a carbon atom. More preferably, the organic polymer PO containing alkoxysilane groups is a polyolefin containing alkoxysilane groups or a polyurethane containing alkoxysilane groups or a polyether containing alkoxysilane groups or a mixed form of these polymers.
  • the organic polymer containing reactive silane groups is a polyether containing alkoxysilane groups.
  • the organic polymer PO containing alkoxysilane groups preferably has an average of 1 .3 to 4, especially 1 .5 to 3, more preferably 1 .7 to 2.8, alkoxysilane groups per molecule.
  • the silane groups are preferably terminal.
  • the organic polymer PO containing alkxysilane groups preferably has an average molecular weight, determined by means of GPC against a polystyrene standard, in the range from 1'000 to 30'000 g/mol, especially from 2'000 to 20'000 g/mol.
  • the organic polymer PO containing alkoxysilane groups preferably has a silane equivalent weight of 300 to 25'000 g/eq, especially of 500 to 15’000 g/eq.
  • the organic polymer PO may be solid or liquid at room temperature. It is preferably liquid at room temperature.
  • the organic polymer PO containing alkoxysilane groups is liquid at room temperature, wherein the silane groups are especially dialkoxysilane groups and/or trialkoxysilane groups, more preferably trimethoxysilane groups, methyldimethoxysilane groups, or triethoxysilane groups.
  • organic polymers containing alkoxysilane groups are obtainable from the reaction of organic polymers containing allyl groups with hydrosilanes, optionally with chain extension using, for example, diisocyanates.
  • polyethers containing alkoxysilane groups are obtainable from the copolymerization of alkylene oxides and epoxysilanes, optionally with chain extension using, for example, diisocyanates.
  • organic polymers containing reactive silane groups are obtainable from the reaction of organic polyols with isocyanatosilanes, optionally with chain extension using diisocyanates.
  • polyethers containing alkoxysilane groups are obtainable from the reaction of organic polymers containing isocyanate groups, especially NCO- terminated urethane polymers from the reaction of polyols with a superstoichiometric amount of polyisocyanates, with aminosilanes, hydroxysilanes or mercaptosilanes.
  • This process enables the use of a multitude of inexpensive starting materials of good commercial availability, by means of which it is possible to obtain different polymer properties, for example high extensibility, high strength, low modulus of elasticity, low glass transition point or high weathering resistance.
  • the organic polymer PO containing alkoxysilane groups is obtainable from the reaction of NCO-terminated urethane polyethers with aminosilanes, mercaptosilanes, or hydroxysilanes.
  • Suitable NCO-terminated urethane polymers are obtainable from the reaction of polyols, especially polyether polyols, in particular polyoxyalkylenediols or polyoxyalkylenetriols, preferably polyoxypropylenediols or polyoxypropylenetriols, with a superstoichiometric amount of polyisocyanates, especially diisocyanates.
  • poly(meth)acrylate polyols such as poly(meth)acrylate polyols, polyhydrocarbon polyols, in particular polybutadiene polyols, polyhdroxy functional fats or oils, polycarbonate polyols, polyester polyols and polyhydroxy functional acrylonitrilie/butadiene copolymers are suitable.
  • poly(meth)acrylate polyols such as poly(meth)acrylate polyols, polyhydrocarbon polyols, in particular polybutadiene polyols, polyhdroxy functional fats or oils, polycarbonate polyols, polyester polyols and polyhydroxy functional acrylonitrilie/butadiene copolymers are suitable.
  • small amounts of low molecular weight dihydric or polyhydric alcohols such as diols, glycols, and sugar alcohols may be used as additives.
  • the reaction between the polyisocyanate and the polyol is conducted with exclusion of moisture at a temperature of 50°C to 160°C, optionally in the presence of suitable catalysts, with metered addition of the polyisocyanate in such a way that the isocyanate groups thereof are present in a stoichiometric excess in relation to the hydroxyl groups of the polyol.
  • the excess of polyisocyanate is chosen such that a content of free isocyanate groups of 0.1 % to 5% by weight, preferably 0.2% to 4% by weight, more preferably 0.3% to 3% by weight, based on the overall polymer, remains in the resulting urethane polymer after the reaction of all hydroxyl groups.
  • HDI hexamethylene 1 ,6- diisocyanate
  • IPDI 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane
  • TDI isophorone diisocyanate
  • TDI diphenylmethane 4,4’-, 2,4'- and 2,2'-diisocyanate and any desired mixtures of these is
  • polyether polyols are polyoxyalkylenediols or polyoxyalkylenetriols having a degree of unsaturation lower than 0.02 meq/g, especially lower than 0.01 meq/g, and a mean molecular weight in the range from 400 to 25’000 g/mol, especially 1000 to 20’000 g/mol.
  • polyether polyols As well as polyether polyols, it is also possible to use portions of other polyols, especially polyacrylate polyols, and low molecular weight diols or triols.
  • Suitable aminosilanes for the reaction with an NCO-terminated urethane polyether are primary and secondary aminosilanes. Preference is given to 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 amino-silanes such as 3- aminopropyltrimethoxysilane, 3-aminopropyldimethoxy-methylsilane or N-(2- aminoethyl)-3-aminopropyltrimethoxysilane and Michael acceptors such as acrylonitrile, (meth)acrylic esters, (me
  • Suitable hydroxysilanes for the reaction with an NCO-terminated urethane polyether are especially obtainable from the addition of aminosilanes onto lactones or onto cyclic carbonates or onto lactides.
  • Aminosilanes suitable for the purpose are especially 3-aminopropyltrimeth-oxysilane, 3- aminopropyltriethoxysilane, 4-aminobutyltrimethoxysilane, 4-aminobutyltriethoxysilane, 4-amino-3-methylbutyltrimethoxysilane, 4-amino-3-methylbutyltriethoxysilane, 4-amino-
  • Suitable lactones are especially y-valerolactone, y-octalactone, b-decalactone, and £- decalactone, especially y-valerolactone.
  • Suitable cyclic carbonates are especially 4,5-dimethyl-1 ,3-dioxolan-2-one, 4,4-dimethyl-
  • Suitable lactides are especially 1 ,4-dioxane-2, 5-dione (lactide formed from 2- hydroxyacetic acid, also called “glycolide”), 3, 6-dimethyl-1 ,4-dioxane-2, 5-dione (lactide formed from lactic acid, also called “lactide”) and 3, 6-diphenyl-1 ,4-dioxane-2, 5-dione (lactide formed from mandelic acid).
  • Preferred hydroxysilanes which are obtained in this way are N-(3-triethoxysilylpropyl)-2- hydroxypropanamide, N-(3-trimethoxysilylpropyl)-2-hydroxypropanamide, N-(3- triethoxysilylpropyl)-4-hydroxypentanamide, N-(3-triethoxysilylpropyl)-4- hydroxyoctanamide, N-(3-triethoxysilylpropyl)-5-hydroxydecanamide and N-(3- triethoxysilylpropyl)-2-hydroxypropyl carbamate.
  • suitable hydroxysilanes are also obtainable from the addition of aminosilanes onto epoxides or from the addition of amines onto epoxysilanes.
  • Preferred hydroxysilanes which are obtained in this way are 2-morpholino-4(5)-(2- trimethoxysilylethyl)cyclohexan-1-ol, 2-morpholino-4(5)-(2-triethoxysilyl- ethyl)cyclohexan-1-ol or 1-morpholino-3-(3-(triethoxysilyl)propoxy)propan-2-ol.
  • polyethers containing reactive silane groups are commercially available products, especially the following: MS PolymerTM (from Kaneka Corp.; especially the S203H, S303H, S227, S810, MA903 and S943 products); MS PolymerTM or SilylTM (from Kaneka Corp.; especially the SAT010, SAT030, SAT200, SAX350, SAX400, SAX725, MAX450, MAX951 products); Excestar® (from Asahi Glass Co.
  • MS PolymerTM from Kaneka Corp.; especially the S203H, S303H, S227, S810, MA903 and S943 products
  • MS PolymerTM or SilylTM from Kaneka Corp.; especially the SAT010, SAT030, SAT200, SAX350, SAX400, SAX725, MAX450, MAX951 products
  • Excestar® from Asahi Glass Co.
  • Particularly preferred organic polymers PO containing alkoxysilane groups have end groups of the formula (VIII)
  • R 16 is a linear or branched divalent hydrocarbyl radical which has 1 to 12 carbon atoms and optionally has cyclic and/or aromatic moieties and optionally one or more heteroatoms, especially one or more nitrogen atoms;
  • T is a divalent radical selected from -O-, -S-, -N(R 17 )-, -O-CO-N(R 17 )-, -N(R 17 )-CO-O- and -N(R 17 )-CO-N(R 17 )-, where R 17 is a hydrogen radical or a linear or branched hydrocarbyl radical which has 1 to 20 carbon atoms and optionally has cyclic moieties, and which optionally has an alkoxysilane, ether or carboxylic ester group; and
  • R 14 , R 15 and x have the definitions already given.
  • R 16 is methylene, 1 ,3-propylene or 1 ,4-butylene, where butylene may be substituted by one or two methyl groups.
  • R 16 is a methylene radical
  • T is a divalent radical selected from -O-, -S-, -N(R 17 )-, -O-CO-N(R 17 )-, -N(R 17 )-CO-O- and -N(R 17 )-CO-N(R 17 )-, where R 17 is a hydrogen radical or a linear or branched hydrocarbyl radical which has 1 to 20 carbon atoms and optionally has cyclic moieties;
  • R 14 is in particular a methyl or ethyl radical
  • R 15 is preferably a methyl radical; and x is preferably 0 or 1 .
  • the multi-component composition further comprises at least one liquid epoxy resin EP.
  • Suitable liquid epoxy resin EP comprises customary technical epoxy resins which are fluid at room temperature and have a glass transition temperature of below 25°C. They are obtained conventionally, more particularly from the glycidylization of compounds having at least two active hydrogen atoms, more particularly polyphenols, polyols or amines, by reaction with epichlorohydrin.
  • liquid epoxy resin EP are in particular aliphatic or cycloaliphatic epoxy resins, more particularly
  • - glycidyl ethers of saturated or unsaturated, branched or unbranched, cyclic or openchain di-, tri- or tetra-functional C2 to C30 alcohols, more particularly ethylene glycol, propylene glycol, butylene glycol, hexanediol, octanediol, polypropylene glycols, dimethylolcyclohexane, neopentyl glycol, dibromoneopentyl glycol, castor oil, trimethylolpropane, trimethylolethane, pentaerythritol, sorbitol or glycerol, or alkoxylated glycerol or alkoxylated trimethylolpropane;
  • N-glycidyl derivatives of hydantoins, amides or heterocyclic nitrogen bases such as, in particular, triglycidyl cyanurate or triglycidyl isocyanurate.
  • liquid epoxy resin EP are aromatic epoxy resins, more particularly
  • polyphenols more particularly of resorcinol, hydroquinone, pyrocatechol, 2,2-bis(4-hydroxyphenyl)propane (bisphenol A), bis(hydroxy- phenyl)methane (bisphenol F), bisphenol A/F, bis(4-hydroxy-3-methyl- phenyl)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)hex
  • aromatic amines more particularly of aniline, toluidine, 4- aminophenol, 4,4’-methylenediphenyldiamine, 4,4’-methylenediphenyldi(N- methyl)amine, 4,4'-[1 ,4-phenylenebis(1-methylethylidene)]bisaniline (bisaniline P) or 4,4'-[1 ,3-phenylenebis(1 -methylethylidene)]bisaniline (bisaniline M).
  • liquid epoxy resin EP is diglycidyl ethers of bisphenol A or bisphenol F or bisphenol A/F, as are available commercially, for example, from Dow, Huntsman or Momentive. These liquid epoxy resins have readily manageable viscosity and allow high strengths and resistance properties.
  • the composition preferably comprises between 2 wt.-% and 10 wt.-%, preferably between 2.5 wt.-% and 7.5 wt.-%, in particular between 3 wt.-% and 6 wt.-%, based on the total composition, of said liquid epoxy resin EP.
  • a composition of this kind exhibits high strength in conjunction with good stretchability and tough elastic properties. Particularly surprising here is the circumstance that such materials display good stretchability even in combination with very high strengths.
  • the multi-component composition further comprises at least one polyamine PA.
  • This polyamine PA serves as hardener for epoxy resin EP and should be suitable for this purpose.
  • polyamine PA should contain at least 2 amine hydrogens that can react with epoxy resins in order to be suitable as hardener for epoxy resins.
  • Amine hydrogens are part of primary and secondary amino groups.
  • Polyamines containing exclusively tertiary amino groups and thus no amine hydrogens are hence not suitable as polyamine PA.
  • Suitable as polyamine PA are in particular compounds or polymers with at least two amine hydrogens, including at least two primary and/or secondary amino groups.
  • polyamine PA has at least one primary amino group, more preferably at least two primary amino groups.
  • Suitable polyamines PA include, for example
  • aliphatic, cycloaliphatic or arylaliphatic primary diamines e.g., ethylenediamine, 1 ,2-propanediamine, 1 ,3-propanediamine, 2-methyl-1 ,2- propanediamine, 2,2-dimethyl-1 ,3-propanediamine, 1 ,3-butanediamine, 1 ,4- butanediamine, 1 ,3-pentanediamine (DAMP), 1 ,5-pentanediamine, 1 ,5-diamino-2- methylpentane (MPMD), 2-butyl-2-ethyl-1 ,5-pentanediamine (C11-neodiamine), 1 ,6- hexanediamine, 2,5-dimethyl-1 ,6-hexanediamine, 2,2,4- and 2,4,4- trimethylhexamethylenediamine (TMD), 1 ,7-heptanediamine, 1 ,8-octanediamine, 1 ,
  • aliphatic primary diamines containing ether groups e.g., bis(2-aminoethyl)ether, 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-tgrioxatridecane-1 ,13-diamine and higher oligomers of these diamines, bis-(3-aminopropyl)polytetrahydrofuranes and other polytetrahydrofuranediamines having molecular weights ranging, e.g., from 350 to 2000, as well as polyoxyalkylenediamines.
  • ether groups e.g., bis(2-aminoeth
  • polyoxyalkylene diols are products of the amination of polyoxyalkylene diols and can, for example, be obtained under the name Jeffamine® (from Huntsman), under the name Polyetheramin (from BASF) or under the name PC Amine® (from Nitroil).
  • Particularly suitable polyoxyalkylenediamines are Jeffamine® D- 230, Jeffamine® D-400, Jeffamine® D-2000, Jeffamine® XTJ-511 , Jeffamine® ED-600, Jeffamine® ED-900, Jeffamine® ED-2003, Jeffamine® XT J-568, Jeffamine® XTJ-569, Jeffamine® XTJ-523, Jeffamine® XTJ-536, Jeffamine® XTJ-542, Jeffamine® XTJ-559, Jeffamine® EDR-104, Jeffamine® EDR-148, Jeffamine® EDR-176; Polyetheramin D 230, Polyetheramin D 400, and Polyetheramin D 2000, PC Amine® DA 250, PC Amine® DA 400, PC Amine® DA 650, and PC Amine® DA 2000;
  • - Polyamines having secondary amino groups e.g., diethylenetriamine (DETA), dipropylenetriamine (DPTA), bishexamethylenetriamine (BHMT), 3-(2-aminoethyl)aminopropylamine, N3-(3- aminopentyl)-1 ,3-pentanediamine, N5-(3-aminopropyl)-2-methyl-1 ,5-pentanediamine, N5-(3-amino-1-ethylpropyl)-2-methyl-1 ,5-pentanediamine, N,N’-dibutylethylenediamine; N,N’-di-tert.butyl-ethylenediamine, N,N’-diethyl-1 ,6-hexanediamine, 1-(1- methylethylamino)-3-(1-methylethylaminomethyl)-3,5,5-trimethylcyclohexane (Jefflink® 754 from Huntsman),
  • Polyamidoamines which are the reaction products of a mono- or polybasic carboxylic acid or the esters or anhydrides thereof, in particular the reaction products of a dimer fatty acid, and a aliphatic, cycloaliphatic or aromatic polyamine used in a stoichiometric excess, in particular a polyalkyleneamine such as, e.g., DETA or triethylenetetramine (TETA), in particular the commercially available polyamidoamines Versamid® 100, 125, 140, and 150 (from Cognis), Aradur® 223, 250, and 848 (from Huntsman), Euretek®3607, Euretek® 530 (from Huntsman), Beckopox® EH 651 , EH 654, EH 655, EH 661 , and EH 663 (from Cytec);
  • a polyalkyleneamine such as, e.g., DETA or triethylenetetramine (TETA)
  • TETA triethylenetetra
  • PEI Polyethyleneimines
  • polyethyleneimine derived from the polymerization of ethyleneimine.
  • a suitable polyethyleneimine typically has an average molecular weight in the range from 250 to 25,000 g/mol and contains tertiary, secondary, and primary amino groups.
  • Polyethyleneimines can be obtained, for example, under the trade name Lupasol® (from BASF), for example, the types Lupasol® FG, Lupasol® G20, and Lupasol® PR 8515.
  • polyamine PA contains at least two primary amino groups.
  • those especially preferred are aliphatic and cycloalphatic polyamines, in particular diamines, and polyetheramines, in particular polyether diamines.
  • polyamine PA comprises or consists of at least one polyetheramine.
  • Suitable polyetheramines are polyoxyalkylenes or polyoxyalkylated compounds having terminal amino groups, of the kind available commercially, for example, under the tradenames Jeffamine® (from Huntsman), Polyetheramine (from BASF) or PC Amine® (from Nitroil), more particularly the following:
  • polyetherdiamines having terminal 2-aminopropyl or 2-aminobutyl groups, more particularly Jeffamine® D-230, Jeffamine® D-400 or Jeffamine® D-2000, Jeffamine® D-4000, Jeffamine® XTJ-582, Jeffamine® XTJ-578, Jeffamine® HK-511 , Jeffamine® ED-600, Jeffamine® ED-900, Jeffamine® ED-2003, Jeffamine® XTJ-568, Jeffamine® XTJ-569, Jeffamine® THF-100, Jeffamine® THF-140, Jeffamine® THF-230, Jeffamine® XTJ-533 or Jeffamine® XTJ-536 (all from Huntsman).
  • the polyetheramine used as polyamine PA preferably has an average molecular weight in the range from 200 to 500 g/mol.
  • Particularly preferred polyetheramines are polyetherdiamines or -triamines having primary amino groups and having an average molecular weight in the range from 200 to 500 g/mol, more particularly Jeffamine® D-230, Jeffamine® D-400 Jeffamine® XTJ-582, Jeffamine® HK-511 , Jeffamine® XTJ-568, Jeffamine® T-403 or Jeffamine® XTJ-566 (all from Huntsman), or corresponding grades from BASF or from Nitroil.
  • the multi-component composition comprises comprises between 0.2 wt.-% and 2.5 wt.-%, preferably between 0.25 wt.-% and 2.0 wt.-%, in particular between 0.5 wt.-% and 1.5 wt.-%, based on the total composition, of said polyamine PA.
  • a composition of this kind exhibits high strength in conjunction with good stretchability and tough elastic properties.
  • the multi-component curable composition according to present invention comprises water.
  • Water should however not be present in the same component as moisture- reactive ingredients, such as polymer PO, in sufficient amounts to initiate pre-mature cross-linking or curing of these ingredients within the sealaed component before mixing with the other components.
  • Addition of free water is thus preferred in cases where an especially fast curing is intended or in cases where the naturally present content of free or chemically accessible water within the composition (e.g., absorbed on fillers Fl) is too low to effect curing of the polymers PO.
  • Water may be added in free form (as liquid water), or in otherwise chemically accessible form. This is not particularly limited, as long as the water remains accessible and chemically active to react with moisture-reactive ingredient of the composition after mixing of the components of the multi-component curable composition. This may also be the case when the used fillers Fl contain significant amounts of chemically accessible (in particular adsorbed) water, which might in such cases be sufficient for enabling proper curing of the polymers PO.
  • water is added in free form.
  • suitable emulsifiers include common surfactants, for example ethoxylated linear fatty alcohols. Suitable such emulsifiers are for example available under the trade name Disponil® by BASF.
  • the multi-component curable composition preferably comprises between 0.1 wt.-% and 2.0 wt.-%, in particular between 0.1 wt.-% and 1.5 wt.-%, preferably between 0.15 wt.-% and 1.0 wt.-%, particularly between 0.15 wt.-% and 0.5 wt.-%, preferably between 0.2 wt.-% and 0.4 wt.-%, in particular between 0.25 wt.-% and 0.35 wt.-%, based on the total composition, of water in liquid or chemically accessible form.
  • the multi-component curable composition optionally but preferably comprises an accelerator AC for accelerating the reaction between liquid epoxy resin EP and polyamine PA.
  • an accelerator AC for accelerating the reaction between liquid epoxy resin EP and polyamine PA.
  • an accelerator AC has the advantage that the composition cures faster after mixing of its components, especially at lower temperatures (e.g., room temperature or below).
  • Suitable accelerators AC are substances which accelerate the reaction between amino groups and epoxide groups, in particular acids or compounds hydrolyzable to acids, in particular organic carboxylic acids such as acetic acid, benzoic acid, salicylic acid, 2- nitrobenzoic acid, lactic acid, organic sulfonic acids such as methanesulfonic acid, p- toluenesulfonic acid or 4-dodecylbenzenesulfonic acid, sulfonic acid esters, other organic or inorganic acids such as in particular phosphoric acid, or mixtures of the abovementioned acids and acid esters; Tertiary amines such as in particular 1 ,4- diazabicyclo [2.2.2] octane, triethanolamine, imidazoles such as in particular N- methylimidazole, N-vinylimidazole or 1 ,2-dimethylimidazole, salts of such tertiary amines, quaternary ammonium
  • accelerator AC Most preferred as accelerator AC among those is salicylic acid or 2,4,6- tris(dimethylaminomethyl)phenol or 2,4,6-tris(N,N-dimethyl-4-amino-2-azabutyl) phenol or a combination thereof.
  • the multi-component curable composition thus preferably comprises an accelerator AC for the reaction between epoxides and amines, in particular with an amount of between 0.1 wt.-% and 1.5 wt.-%, preferably between 0.2 wt.-% and 1.0 wt.-%, more preferably between 0.25 wt.-% and 0.75 wt.-% of said accelerator AC based on the total composition.
  • Accelerator AC is preferably included in a different component than liquid epoxy resin EP
  • the multi-component curable composition optionally but preferably comprises at least one catalyst CA for the curing of silane-functional polymers.
  • catalyst CA is advantageous to ensure a sufficient curing rate given the fact that low amounts of reactive polymers are used.
  • a catalyst is not in every case necessary.
  • a catalyst may be omitted.
  • Suitable catalysts are especially metal compounds and/or basic nitrogen or phosphorus compounds.
  • Suitable metal compounds are especially compounds of tin, titanium, zirconium, aluminum or zinc, especially diorganotin(IV) compounds such as, in particular, dibutyltin(IV) diacetate, dibutyltin(IV) dilaurate, dibutyltin(IV) dineodecanoate or dibutyltin(IV) bis(acetylacetonate) and dioctyltin(IV) dilaurate, and also titanium(IV) or zirconium(IV) or aluminum(lll) or zinc(ll) complexes, especially with alkoxy, carboxylate, 1 ,3-diketonate, 1 ,3-ketoesterate or 1 ,3-ketoamidate ligands.
  • diorganotin(IV) compounds such as, in particular, dibutyltin(IV) diacetate, dibutyltin(IV) dilaurate, dibutyltin(IV) dineodecan
  • Suitable basic nitrogen or phosphorus compounds are especially imidazoles, pyridines, phosphazene bases, secondary or tertiary amines, hexahydrotriazines, biguanides, guanidines, or amidines.
  • Nitrogen-containing compounds suitable as catalysts CA are in particular amines, especially N-ethyl-diisopropylamine, N,N,N’,N’-tetramethylalkylenediamines, 1 ,4- diazabicyclo[2.2.2]octane; amidines such as especially 1 ,8-diazabicyclo[5.4.0]undec-7- ene (DBU), 1 ,5-diazabicyclo[4.3.0]non-5-ene (DBN), 6-dibutylamino1 ,8-diazabicyclo- [5.4.0]undec-7-ene; guanidines such as especially tetramethylguanidine, 2-guanidino- benzimidazole, acetylacetone-guanidine, 3-di-o-tolyl-guanidine, 2-tert-butyl-1 , 1 ,3,3- tetramethyl guanidine; biguanides such as big
  • catalyst CA for example a metal compound and a nitrogen-containing compound.
  • the multi-component curable composition thus preferably comprises a catalyst CA for for the curing of silane-functional polymers, in particular with an amount of between 0.005 wt.-% and 0.5 wt.-%, preferably between 0.01 wt.-% and 0.25 wt.-%, more preferably between 0.025 wt.-% and 0.15 wt.-% of said catalyst CA based on the total composition.
  • Catalyst CA is preferably included in a different component than polymer PO.
  • the composition according to the present invention comprises more than 70 wt.-%, based on the total composition, of at least one thermally conductive filler Fl.
  • the composition comprises up to 95 wt.-%, in particular up to 92 wt.-%, preferably between 75 wt.-% and 90 wt.-%, more preferably between 80 wt.-% and 85 wt.-%, based on the total composition, of said thermally condicutive filler Fl.
  • the thermally conductive filler Fl is not particularly limited.
  • Suitable thermally conductive fillers are in particular those that have a coefficient of thermal conductivity that is greater than 5 W/mK, preferably greater than 10 W/mK, more preferably greater than 15 W/mK.
  • thermally conductive fillers examples include alumina, alumina trihydrate or aluminum trihydroxide, silicon carbide, boron nitride, aluminium nitride, zinc oxide, aluminosilicate, diamond, and graphite, or mixtures thereof. Particularly preferred are aluminium trihydroxide (ATH), and aluminium oxide, with ATH being the most preferred.
  • the filler Fl should be in powder form or at least particulate, in order to ensure homogeneous compounding in its high amounts.
  • the thermally conductive filler Fl has a broad particle size distribution characterized by a ratio of D90/D50 of at or about 3 or more.
  • the thermally conductive filler is ATH or aluminium oxide having a broad particle size distribution characterized by a ratio of D90/D50 of at or about 3 or more, most preferably ATH.
  • thermally conductive fillers having a bimodal particle size distribution are also preferred. A bimodal distribution is when, for example, the ratio D90/D50 is at or about 3 or more, more preferably at or about 5 or more, more particularly preferably at or about 9 or more.
  • particles having a D50 of 5 to 20 microns and a D90 of 70 to 90 microns particularly a D50 of 7-9 microns and a D90 of 78-82 microns.
  • Particle size can be determined using laser diffraction.
  • Preferred are aluminium oxide and ATH having a bimodal distribution, particularly ATH.
  • the filler Fl comprises or consists of aluminium oxide and aluminium hydroxide.
  • This combination has the advantage that it shows especially good thermal conductivity and at the same time excellent flame-retardant properties. This makes it especially suitable for battery assemblies.
  • the thermally conductive filler Fl is preferably present in the final adhesive at a concentration that gives a thermal conductivity of at or about 1 .5 W/mK or more, preferably at or about 2.0 or more, more preferably at or about 2.5 or more.
  • the thermally conductive filler Fl may be present in any component of the multicomponent curable composition according to the present invention.
  • filler Fl may be present in component A, in component B, or, preferably, in both components A and B.
  • thermally conductive filler Fl is present in in both components A and B, as this reduces the amount of mixing required to properly distribute the thermally conductive filler Fl within the composition when components A and B are mixed. Furthermore, this allows for a broader range of mixing ratios between the components while ensuring a sufficiently high amount of filler Fl within the composition.
  • the multi-component composition according to the present invention preferably comprises at least one plasticizer PL.
  • the composition may be formulated without plasticizer, but it is preferred that small amounts (e.g., from 1 wt.-% up to 10 wt.-%, 12 wt.-%, or 15 wt.-%, based on the total composition) of plasticizer are used for ease of compounding and resulting application and mechanical properties.
  • the composition additionally comprises between 1.5 wt.-% and 12.5 wt.-%, in particular between 2.5 wt.-% and 10 wt.-%, preferably between 3 wt.-% and 9 wt.-%, in particular between 4 wt.-% and 8 wt.-%, based on the total composition, of at least one plasticizer PL.
  • the plasticizer PL may be any of the plasticizers commonly used in compositions based on silane-functional polymers or mixtures of different such plasticizers.
  • carboxylic esters such as phthalates, especially dioctyl phthalate, bis(2- ethylhexyl) phthalate, bis(3-propylheptyl) phthalate, diisononyl phthalate or diisodecyl phthalate, diesters of ortho-cyclohexane-dicarboxylic acid, especially diisononyl 1 ,2- cyclohexanedicarboxylate, adipates, especially dioctyl adipate, bis(2-ethylhexyl) adipate, azelates, especially bis(2-ethylhexyl) azelate, sebacates, especially bis(2- ethylhexyl) sebacate or diisononyl sebacate, glycol ethers, glycol esters, organic phosphoric or sulfonic esters, sulfonamides, polybutenes, or
  • polymeric plasticizers are also suitable. These have the advantage of lower migration tendency into surrounding areas and lower contribution to VOC levels.
  • polymeric plasticizer herein means a polymeric additive that is liquid at room temperature and contains no hydrolyzable silane groups. In contrast to traditional plasticizers, such as phthalates, the polymeric plasticizers generally have a higher molecular weight.
  • the polymeric plasticizer has an average molecular weight M n of 500 to 12’000 g/mol, in particular 1’000 to 10’000 g/mol, more preferably 2’500 to 5’000 g/mol.
  • Suitable polymeric plasticizers include polyols, such as those suitable for the production of the organic polymers PO mentioned there, as long as they are liduid at room temperature, and polyols where the OH-groups have been reacted to chemically inert functional groups.
  • Preferred polyols suitable as polymeric plasticizers include polyether polyols, polyester polyols, polyhydrocarbon polyols, polybutadiene polyols, and poly(meth)acrylate polyols. Particularly preferred are polyether polyols, especially those with an average molecular weight of M n of 500 to 12’000 g/mol, especially 1 ’000 to 10’000 g/mol, more preferably 2’500 to 5’000 g/mol.
  • plasticizers PL are low molecular weight diesters of polyether diols, in particular tri(ethylenglycol)bis-2-ethylhexanoate, which is available under the trade name Eastman® TEG-EH by Eastman.
  • plasticizers PL for the multi-component curable composition according to the present invention comprise or consist of a trialkyl and/or triaryl phosphate, for example triethyl phosphate, tricresyl phosphate, triphenyl phosphate, diphenyl cresyl phosphate, isodecyl diphenyl phosphate, tris(1 ,3-dichloro-2-propyl) phosphate, tris(2- chloroethyl) phosphate, tris(2-ethylhexyl) phosphate, tris(chloroisopropyl) phosphate, tris(chloropropyl) phosphate, isopropylated triphenyl phosphate, mono-, bis- or tris(isopropylphenyl) phosphates.
  • a trialkyl and/or triaryl phosphate for example triethyl phosphate, tricresyl phosphate, tripheny
  • Preferred trialkyl and/or triaryl phosphate plasticizers PL are tris-(2-ethylhexyl)-phosphate (sold under the trade name Disflamoll® TOF by Lanxess), cresyl diphenyl phosphate, tricresyl phosphate, and triphenyl phosphate (all sold under the trade name range Disflamoll® by Lanxess).
  • Trialkyl and/or triaryl phosphate plasticizers have the advantage that they improve the flame-retardant properties of the composition.
  • Plasticizers PL may be present in one or several components of the multi-component curable composition according to the invention. Preferably, plasticizer PL is present in all components of the present invention, especially if filler Fl is also present, as plasticzer PL facilitates a homogeneous compounding of highly filled components.
  • the multi-component curable composition furthermore may comprise at least one dispersion additive D.
  • Dispersion additives are well known in the field of coating formulations containing fillers and pigments. They are also known as dispersants or wetting agents and facilitate the compounding of solids into a liquid matrix.
  • dispersion additive D may facilitate incorporation of very high amounts (i.e. , more than 85 wt.-% based on the total composition, or higher) of filler Fl within the composition.
  • all common dispersion additives are suitable, and their suitable amount for a given formulation depends on the type of dispersion additive and relative amount of filler Fl and other consituents, such as polymer PO.
  • the composition comprises said dispersion additive D with an amount of between 0.5 and 5.0 wt.-%, preferably between 0.7 and 4.0 wt.-%, in particular between 1.0 and 3.0 wt.-%, based on the total composition.
  • An especially preferred dispersion additive D is an ammonium salt or alkyl ammonium salt of a polymer or compolymer containing carboxylate and/or phosphate groups, preferably a polyether and/or polyester polymer containing carboxylate and/or phosphate groups.
  • Suitable such dispersion additives D are, for example, Byk-W 996, Byk-W 969, Byk-W 985 (available from Altana) and Disparlon DA-234, DA-325, and DA-375 (available from King Industries).
  • the multi-component curable composition according to the present invention furthermore preferably comprises organosilanes or oligomers of organosilanes, in particular monomeric or oligomeric organofunctional alkoxysilanes.
  • the composition comprises between 0.1 wt.-% and 2.5 wt.-%, preferably between 0.2 wt.-% and 1 .5 wt.-%, preferably between 0.25 wt.-% and 1 .0 wt.-%, in particular between 0.5 wt.-% and 0.75 wt.-%, based on the total composition, of organosilanes or oligomers of organosilanes, in particular comprising or consisting of aminosilanes or oligomers thereof.
  • Organosilanes have various advantages. For example, they may act as desciccant or drying agent, in particular vinyl trimethoxysilane and/or propyl trimethoxysilane.
  • organosilanes have co-catalytic activity, in particular aminosilanes such as 3- aminopropyl trimethoxysilane, and/or they act as adhesion promotors, such as 3- glycidoxypropyl trimethoxysilane. Nevertheless, in some embodiments the composition does not contain adhesion-promoting silanes, such as amino silanes or glycidoxy silanes.
  • a composition free of adhesion-promoting silanes, in particular amino-functional and/or glycidoxy-functional silanes, has the advantage that the composition may be easily removed from the substrate when the object bonded with the composition needs to be disassembled, for example during a battery replacement operation.
  • Preferred organosilanes acting, for example, as adhesion promoters and/or crosslinkers are in particular aminosilanes, mercaptosilanes, epoxysilanes, (meth)acryloylsilanes, anhydridosilanes, carbamatosilanes, alkylsilanes or iminosilanes, oligomeric forms of these silanes, adducts formed from primary aminosilanes with epoxysilanes or (meth)acryloylsilanes or anhydridosilanes, amino-functional alkylsilsesquioxanes, 3- glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane or 3- ureidopropyltrimethoxysilane, or oligomeric forms of these silanes.
  • Preferred organosilanes acting as desiccants or drying agents are in particular tetraethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, propyltrimethoxysilane, or organoalkoxysilanes having a functional group in the a-position to the silane group, especially N-(methyldimethoxysilylmethyl)-O-methylcarbamate, (methacryloyloxymethyl)silanes, and methoxymethylsilanes.
  • Preferred organosilanes acting as co-catalysts are in particular aminosilanes.
  • the organosilanes preferably comprised in the composition may be monomeric organosilanes or oligomeric organosilanes.
  • R 2 is a monovalent alkyl radical having 1 to 6 carbon atoms, preferably 1 or 2 carbon atoms, most preferably a methyl radical;
  • R 3 is a monovalent, linear or branched hydrocarbon radical having 1 to 20 carbon atoms and optionally containing olefinic, aromatic and/or cyclic moieties and optionally containing heteroatoms selected from O, N, S, and Si;
  • R 3 is an aminoalkyl radical selected from -C P H2 P -NH2, -C P H 2p -NH-R 5 , -C P H2 P -NH-CdH2d-NH 2 , -C P H2 P -NH-CdH2d-NH-CeH2e-NH 2 , -C P H 2p -NH-CdH2d-NH-R 5 , and -C P H 2p -NH-CdH2d-NH-CeH2e-NH-R 5 ;
  • R 5 is a monovalent linear, branched, or cyclic alkyl or arakyl radical having 1 to 12 carbon atoms, preferably 1 to 6 carbon atoms; index p is an integer with a value of 1 to 6; indices d and e are independently integers with a value of 2 to 6.
  • R 3 is a glycidoxyalkyl radical. In further preferred embodiments, R 3 is a mercapto- or hydroxyalkyl radical.
  • Suitable oligomeric silanes are linear, cyclic, or branched oligomers of the aforementioned monomeric organosilanes. They may be oligomers of one or more than one type of organosilane.
  • oligomeric organosilanes are used in greater amounts compared to purely monomeric silanes.
  • Preferred monomeric or oligomeric aminofunctional alkoxysilanes include N-(n-butyl)-3- aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3- aminopropyldimethoxymethyl-silane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyldimethoxymethylsilane, N-(2-aminoethyl)-N'-[3- (trimethoxysilyl)-propyl]ethylenediamine and oligomers obtained from the condensation of the mentioned aminosilanes, optionally oligomerized together with alkylalkoxysilanes, in particular methyltrimethoxysilane, ethyltrimethoxysilane, propyltrimethoxysilane, vinyltrimethoxysilane, n-buty
  • Preferred glycidoxyfunctional organosilanes are glycidoxypropyltrimethoxysilane and glycidoxypropyltriethoxysilane and oligomers containing glycidoxypropyl groups, stemming from monomeric glycidoxypropylalkxoysilanes condensated with the aforementioned organosilanes or with themselves.
  • Organsilanes are preferably present in the same component of the multi-component composition as polymer PO.
  • the multi-component composition may comprise further constituents, especially the following auxiliaries and additives:
  • additional desiccants or drying agents especially orthoformic esters, calcium oxide or molecular sieves
  • additional plasticizers especially reactive plasticizers in the form of monofunctional organic polymers or silanes, i.e. those that are silane-reactive only at one end;
  • inorganic or organic fillers especially baryte (heavy spar), talcs, quartz flours, quartz sand, dolomites, chalk, wollastonites, kaolins, calcined kaolins, mica (potassium aluminum silicate), molecular sieves, magnesium hydroxide, silicas including finely divided silicas from pyrolysis processes, industrially produced carbon blacks, metal powders such as iron or steel, PVC powder or hollow spheres;
  • - fibers especially glass fibers, carbon fibers, metal fibers, ceramic fibers or polymer fibers such as polyamide fibers or polyethylene fibers;
  • thickeners or thixotropy additives especially sheet silicates such as bentonites, derivatives of castor oil, hydrogenated castor oil, polyamides, polyurethanes, urea compounds, fumed (pyrogenic) silicas, cellulose ethers or hydrophobically modified polyoxyethylenes;
  • non-reactive polymers that are preferably solid at room temperature
  • PE polyethylenes
  • PP polypropylenes
  • EVA ethylene-vinyl acetate copolymers
  • APAO atactic poly-a-olefins
  • polyesters and polycarbonates
  • - flame-retardant substances especially the already mentioned filler aluminum hydroxide, magnesium hydroxide, or, in particular, the already mentioned organic phosphoric esters such as, in particular, triethyl phosphate, tricresyl phosphate, triphenyl phosphate, diphenyl cresyl phosphate, isodecyl diphenyl phosphate, tris(1 ,3-dichloro-2-propyl) phosphate, tris(2-chloroethyl) phosphate, tris(2-ethylhexyl) phosphate, tris(chloroisopropyl) phosphate, tris(chloropropyl) phosphate, isopropylated triphenyl phosphate, mono-, bis- or tris(isopropylphenyl) phosphates of different degrees of isopropylation, resorcinol bis(diphenyl phosphate), bisphenol A bis(diphenyl
  • biocides especially algicides, fungicides or substances that inhibit fungal growth; and other substances customarily used in curable compositions. It may be advisable to chemically or physically dry certain constituents before mixing them into the composition, especially if they are stored in the same component as polymer PO.
  • the composition does not contain polydiorganosiloxanes.
  • the composition is preferably produced and stored with exclusion of moisture, especially regarding the component containing polymer PO.
  • all components of the multi-component composition are storage-stable with exclusion of moisture in a suitable package or arrangement, such as, more particularly, a bottle, a canister, a pouch, a bucket, a vat or a cartridge.
  • composition is a multi-component, especially two-component, composition.
  • two-component refers to a composition in which the constituents of the composition are present in two different components which are stored in separate containers.
  • the reactive species i.e. polymer PO and organosilane
  • the reactive species i.e. polymer PO and organosilane
  • Liquid epoxy resin EP and polyamine PA may be included in either one of components A and B, as long as they are not in the same component.
  • polyamine PA is included in component A and epoxy resin EP in component B.
  • Epoxy resin EP and polyamine PA also cure when mixed with each other.
  • Any second or optionally further components is/are mixed with the first component prior to or on application, especially by means of a static mixer or by means of a dynamic mixer.
  • the composition therefore consists the composition is a two-component composition that consists of two individual components A and B that are stored in separated containers and mixed before or during applications to yield the fully mixed curable composition, wherein said component A contains polymer PO, polyamine PA, and optionally organosilanes and/or other optional additives; and said component B contains water, epoxy resin EP and optionally further additives; and wherein thermally conductive filler Fl and all further optional consitutents of the composition are present in either one or both of the components A and B.
  • An especially preferred embodiment of a two-component moisture-curable composition according to the present invention consists of a component A and a component B, wherein said component A comprises, based on component A,
  • plasticizer PL optionally between 1 wt.-% and 15 wt.-%, preferably between 2 wt.-% and 10 wt.-% of said plasticizer PL;
  • component B comprises, based on component B,
  • a preferred volumetric mixing ratio of component A to component B for above two- component composition is between 1 :2 and 2:1 , preferably between 1 :1.5 and 1.5:1 , in particular between 1 :1.2 and 1.2:1 , most preferably 1 :1.
  • the water mentioned for component B may be added accordingly, or it may be present from the beginning as impurity in not previously dried fillers Fl.
  • Fillers Fl may contain, if not dried, up to 1 wt.-% or more of water bound to their surface or within pores. This water is normally not chemically bound but only physisorbed and is able to promote the crosslinking of the polymers PO when the composition is mixed.
  • the curable composition according to the present invention is preferably applied at ambient temperature, such as room temperature, preferably within a temperature range between 0°C and 45°C, especially 5°C to 35°C, and cures under these conditions. However, it can also cure in an accelerated manner at temperatures up to 80°C.
  • the crosslinking reaction of the silane groups commences, if appropriate under the influence of moisture.
  • Silane groups present can condense with silanol groups present to give siloxane groups (Si-O-Si groups).
  • Silane groups present can also be hydrolyzed on contact with moisture to give silanol groups (Si-OH groups) and form siloxane groups (Si-O-Si groups) through subsequent condensation reactions.
  • Si-OH groups silanol groups
  • Si-O-Si groups siloxane groups
  • the catalysts CA described further above accelerate this curing mechanism catalytically.
  • the multi-component composition according to the invention is in principle suitable for a multitude of uses, for example as a molding, elastomer, film or membrane, as a potting compound, sealant, gap filler, adhesive, covering, or coating for construction and industrial applications, for example as a seam seal, cavity seal, electrical insulation compound, assembly adhesive, bodywork adhesive, seal, or gap filler.
  • the composition is particularly suitable as an adhesive, gap filler, potting resin, and/or sealant, especially in automotive manufacturing, for batteries, electronic elements, engine control units, anti-lock breaking and electronic stability control and safety systems, DC/DC converter of hybrid electric vehicles, advanced driver-assistance systems, sensors, or control units.
  • the composition preferably has a pasty consistency with structurally viscous properties.
  • a pasty sealant or adhesive is especially applied to a substrate from standard cartridges which are operated manually, by means of compressed air or with a battery, or from a vat or hobbock by means of a delivery pump or an extruder, optionally by means of an application robot.
  • composition is preferably applied to at least one substrate.
  • Suitable substrates are especially
  • - metals and alloys such as aluminum, iron, steel and nonferrous metals, and also surface-finished metals and alloys such as galvanized or chromed metals or surface coated metals, such as Kynar®- or Duranar®-coated aluminum, and electrolytical ly nickel-plated steel, for example available under the trade name Hilumin® from Tata Steel;
  • resins for example phenolic, melamine or epoxy resins, resin-textile composites and further polymer composites
  • plastics such as polyvinyl chloride (rigid and flexible PVC), acrylonitrile-butadiene- styrene copolymers (ABS), polycarbonate (PC), polyamide (PA), polyesters, poly(methyl methacrylate) (PMMA), epoxy resins, polyurethanes (PUR), polyoxymethylene (POM), polyolefins (PO), polyethylene (PE) or polypropylene (PP), ethylene/propylene copolymers (EPM) and ethylene/propylene/diene terpolymers (EPDM), and also fiber-reinforced plastics such as carbon fiber-reinforced plastics (CFP), glass fiber-reinforced plastics (GFP) and sheet molding compounds (SMC), where the plastics may have been surface-treated by means of plasma, corona or flames;
  • CFRP carbon fiber-reinforced plastics
  • GFP glass fiber-reinforced plastics
  • SMC sheet molding compounds
  • - coated substrates such as powder-coated metals or alloys
  • the substrates can be pretreated prior to the application of the composition, especially by chemical and/or physical cleaning methods or by the application of an adhesion promoter, an adhesion promoter solution or a primer.
  • composition shows in preferred embodiments an excellent adhesion profile on a large variety of unprimed, non-pretreated, and even uncleaned materials.
  • compositions preferably do not contain adhesion promoting organosilanes as described further above.
  • compositions disclosed herein possess in preferred embodiments excellent thermal conductivity, in particular of > 1 .5 W/mK, in preferred embodiments of > 2.0 W/mK, according to ASTM D5470. Other preferred embodiments may have lower thermal conductivity, but instead have higher mechanical properties, e.g., tensile strength and elongation at break.
  • the compositions disclosed herein generally possess low viscosities of less than 200 Pa s at a shear rate of 10 s -1 in their mixed state. Likewise, they possess a low squeeze flow of less than 500 N, in particular less than 250 N, more preferably less than 150 N at a gap with of 0.8 mm according to the measurement specified in the experimental section below.
  • compositions disclosed herein after curing have the advantage of good mechanical properties, including high tensile strength, high elongation at break, and high lap shear strength.
  • Another aspect of the present invention is the use of a multi-component curable composition as described herein to adhesively bond, coat, or seal substrates or as a filler or potting resin for hollow bodies.
  • At least one of the substrates or hollow bodies is part of a battery or an electronic device.
  • the use of the composition gives rise to an article that was bonded, sealed, filled, or coated with the composition according to the invention.
  • the article is especially a built structure, especially a structure built by structural engineering or civil engineering, an industrially manufactured good or a consumable good, especially a domestic appliance or a mode of transport such as, more particularly, an automobile, a bus, a truck, a rail vehicle, a ship, an aircraft, a drone, or a helicopter; or the article may be an installable component thereof, in particulate a battery box or electronic part.
  • Another aspect of the present invention is thus a substrate, adhesively sealed, coated, or bonded by a cured multi-component composition described herein, as well as a hollow body filled with a cured multi-component composition described herein.
  • standard climatic conditions refers to a temperature of 23 ⁇ 1 °C and a relative air humidity of 50 ⁇ 5%.
  • Viscosity was determined on a MCR 302 rheometer (Anton Paar) according to ISO 3219. Measurement parameters were: Rotation 0.1 - 10 s-1 , measurement point at 10 s-1 , temperature 20°C, gap 0.5 mm. Several compositions A and compositions B were measured individually before mixing (Table 7).
  • Thermal conductivity was determined according to ASTM D5470-12 on samples cured during 7 days under standard climatic conditions. For the measurements, a TIM (thermal interface material) testing device (Zentrum fur Warmemanagement, Stuttgart, Germany) using the stationary cylinder method was used. Sample dimensions were: Diameter 30 mm, thickness 2 mm. The pressure parameter of the measurements were 1 , 2, 3, 5, 7, 10 bar.
  • the tensile strength (“TS”), the elongation at break (“EOB”), and the modulus of elasticity at 0.5 to 5.0% elongation (E-modulus, “E-mod”) were determined in accordance with DIN EN 53504 (tensioning speed 10 mm/min) on dumbbells with a length of 75 mm, with a bar length of 30 mm and a bar width of 4 mm, which were produced by punching from films with a thickness of around 2 mm, these films being films of the composition cured after a storage time of 7 days under standard conditions.
  • test specimens were produced by applying the composition for 1 minute in each case after the end of the mixing time, between two aluminium sheets (aluminium sheet thickness 1.5 mm) degreased with isopropanol, in a layer thickness of 1 mm, on an overlapping bond area of 10 x 25 mm.
  • the lap shear strength was determined on these test specimens at room temperature in accordance with DIN EN 1465, the test specimens having been cured prior to measurement for 7 days under standard conditions.
  • Squeeze flow measurements were performed on a Zwick machine properly equipped to determine the forces occurring during the measurements.
  • the test compositions were applied on a 60 mm diameter pressure plate and pressed by a 40 mm pressure stamp, wherein the surfaces of the stamp and the plate were parallel.
  • the measurements were performed under standard climate (23°C, 50% r.h.). In particular, the measurements were performed as follows: After application of the test material on the 60 mm plate, the 40 mm pressure stamp was driven vertically downwards at a speed of 1 mm/s until a gap of 5 mm between the stamp and the plate were reached. At this point the test material must cover the entire surface of the 40 mm pressure stamp.
  • the pressure stamp was further driven down until a 0.3 mm gap was reached, with a speed of 1 mm/s.
  • the required force was evaluated in Newton (N) at a defined gap, e. g. 0.5 mm, 0.8 mm, or 1 mm, according to the specification in the table.
  • Table 1 Compounds used for the example compositions.
  • a series of example two-component compositions was prepared by mixing the ingredients of each respective component A and B shown in Tables 2, 5, 8, and 11 (components A) and Tables 3, 6, 9, and 12 (components B) in the indicated sequence as listed in the table under nitrogen atmosphere in a vacuum mixer until homogeneous pastes were obtained.
  • the individual components A and B were filled into internally coated aluminum spreading piston cartridges that were closed airtight and stored under standard climate conditions for at least 24 h until the testing protocol (e.g, viscosity) was employed (see above for details).
  • the respective components A and B of the compositions were mixed in a volume ratio of 1 :1 and subsequently left for curing during 7 days under standard climate (if not otherwise specified for the respective test method). The test results of these 1 :1 mixtures are shown in T ables 4, 7, 10, ans 13 for selected compositions.
  • Example compositions components A (all numbers in wt.-%, based on the tota individual composition A).
  • Example compositions components B (all numbers in wt.-%, based on the tota individual composition B).
  • Example compositions components A (all numbers in wt.-%, based on the total individual composition A).
  • Example compositions components B (all numbers in wt.-%, based on the total individual composition B).
  • Example compositions components B (al numbers in wt.-%, based on the tota individual composition B).
  • Example compositions components A (all numbers in wt.-%, based on the total individual composition A).
  • Example compositions components B (all numbers in wt.-%, based on the total individual composition B).

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Abstract

L'invention concerne une composition durcissable à composants multiples, comprenant - au moins un polymère organique PO contenant des groupes alcoxysilane ; - au moins une résine époxyde EP liquide ; - au moins une polyamine PA ; - plus de 70 % en poids, sur la base de la composition totale, d'au moins une charge FI thermoconductrice ; - de l'eau ; - éventuellement des additifs choisis parmi des catalyseurs de durcissement, des accélérateurs, des plastifiants, des organosilanes, des stabilisants et des colorants ; ladite résine époxyde EP liquide et ladite polyamine PA n'étant pas présentes dans le même composant, et ledit polymère organique PO et ladite eau n'étant pas présents dans le même composant. La composition durcissable à composants multiples présente des propriétés mécaniques améliorées et une applicabilité facile au même titre qu'une excellente conductivité thermique et est particulièrement appropriée en tant qu'adhésif, élément de remplissage d'espace ou produit d'étanchéité approprié pour les applications de revêtement électrolytique et la liaison de batteries, en particulier dans l'assemblage des automobiles électriques.
PCT/EP2024/065431 2023-06-06 2024-06-05 Composition durcissable thermoconductrice Ceased WO2024251789A1 (fr)

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EP24729874.8A EP4724511A1 (fr) 2023-06-06 2024-06-05 Composition durcissable thermoconductrice
CN202480025865.5A CN120958055A (zh) 2023-06-06 2024-06-05 导热可固化组合物

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0186191A2 (fr) 1984-12-26 1986-07-02 Kanegafuchi Chemical Industry Co., Ltd. Composition durcissable de résine contenant une résine époxyde et un polymère élastomère contenant du silicium
EP0370464A2 (fr) 1988-11-21 1990-05-30 Kanegafuchi Chemical Industry Co., Ltd. Composition de résine durcissable
EP1695989A1 (fr) * 2003-12-18 2006-08-30 Kaneka Corporation Composition durcissable
US20220073738A1 (en) * 2019-02-13 2022-03-10 Sika Technology Ag Thermally conductive curable composition
CN115926719A (zh) 2022-12-27 2023-04-07 浙江多邦新材料有限公司 一种双组分硅烷改性聚醚型三防胶及其制备方法
WO2023149328A1 (fr) * 2022-02-01 2023-08-10 株式会社スリーボンド Composition de résine thermoconductrice à deux constituants et produit durci

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0186191A2 (fr) 1984-12-26 1986-07-02 Kanegafuchi Chemical Industry Co., Ltd. Composition durcissable de résine contenant une résine époxyde et un polymère élastomère contenant du silicium
EP0370464A2 (fr) 1988-11-21 1990-05-30 Kanegafuchi Chemical Industry Co., Ltd. Composition de résine durcissable
EP1695989A1 (fr) * 2003-12-18 2006-08-30 Kaneka Corporation Composition durcissable
US20220073738A1 (en) * 2019-02-13 2022-03-10 Sika Technology Ag Thermally conductive curable composition
WO2023149328A1 (fr) * 2022-02-01 2023-08-10 株式会社スリーボンド Composition de résine thermoconductrice à deux constituants et produit durci
CN115926719A (zh) 2022-12-27 2023-04-07 浙江多邦新材料有限公司 一种双组分硅烷改性聚醚型三防胶及其制备方法

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