EP2158236A1 - Composition de (méth)acrylate élastique - Google Patents

Composition de (méth)acrylate élastique

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Publication number
EP2158236A1
EP2158236A1 EP08708185A EP08708185A EP2158236A1 EP 2158236 A1 EP2158236 A1 EP 2158236A1 EP 08708185 A EP08708185 A EP 08708185A EP 08708185 A EP08708185 A EP 08708185A EP 2158236 A1 EP2158236 A1 EP 2158236A1
Authority
EP
European Patent Office
Prior art keywords
meth
composition
acrylate
composition according
lmax
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP08708185A
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German (de)
English (en)
Inventor
Patricia Egli
Fabio Cirillo
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sika Technology AG
Original Assignee
Sika Technology AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sika Technology AG filed Critical Sika Technology AG
Priority to EP08708185A priority Critical patent/EP2158236A1/fr
Publication of EP2158236A1 publication Critical patent/EP2158236A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/04—Polymers provided for in subclasses C08C or C08F
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • 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
    • C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers

Definitions

  • the invention relates to the field of elastic (meth) acrylate adhesives, sealants and coatings.
  • US 3,994,764 describes the addition of room temperature solid non-reactive elastomers to the (meth) acrylate composition.
  • the disadvantage of such compositions is that the (meth) acrylate monomers must be chosen so that the solid elastomer dissolves therein.
  • This claim is met to a suitable extent only methyl methacrylate, which in turn has the disadvantage that it spreads a very unpleasant odor in the application and is highly flammable.
  • WO 02/070619 describes elastic (meth) acrylate compositions comprising a monofunctional (meth) acrylate monomer having a high glass transition temperature (Tg), a monofunctional (meth) acrylate co-monomer and a liquid elastomer.
  • Tg glass transition temperature
  • PVC polyvinyl chloride
  • compositions which are suitable for optimum elastic properties for structural and semi-structural applications, in particular for the bonding of glass with PVC and / or aluminum.
  • compositions according to claim 1 solve this problem.
  • compositions according to the invention have a very high elasticity, which allows them to absorb deformations, as they occur for example by the so-called bimetallic effect when applied to substrates with different linear thermal expansion coefficients. Such deformations also occur, for example, in the bonding of glass to metals or plastics.
  • compositions according to the invention have optimum adhesion to a large number of substrates, but especially to glass, PVC and aluminum. Further aspects of the invention are the subject of further independent claims. Particularly preferred embodiments of the invention are the subject of the dependent claims.
  • the present invention relates to a composition
  • a composition comprising at least one monomer A selected from the group consisting of methyl methacrylate (MMA), tetrahydrofurfuryl methacrylate (THFMA), cyclohexyl methacrylate (CHMA), isobornyl methacrylate (IBMA) and trimethylcyclohexyl methacrylate (TMCHMA), in particular methyl methacrylate (MMA) or tetrahydrofurfuryl methacrylate (THFMA);
  • MMA methyl methacrylate
  • THFMA tetrahydrofurfuryl methacrylate
  • CHMA cyclohexyl methacrylate
  • IBMA isobornyl methacrylate
  • TMCHMA trimethylcyclohexyl methacrylate
  • MMA methyl methacrylate
  • THFMA tetrahydrofurfuryl methacrylate
  • a co-monomer B which is ethylhexyl acrylate (EHA) or maleic acid diallyl ester (MADAE); such as at least one elastomer C of the formula (I).
  • EHA ethylhexyl acrylate
  • MADAE maleic acid diallyl ester
  • R is either a hydrogen atom or a methyl group.
  • X is a polymeric polyol after removal of two OH groups and Y is O or NR ", where R" is a hydrocarbon radical or a hydrogen atom, preferably a hydrogen atom.
  • the elastomer C of the formula (I) is liquid at room temperature, which includes viscous and high-viscosity elastomers.
  • the composition may contain a single monomer A or it may contain a mixture of different monomers A.
  • ⁇ LmZn (A) corresponds to a value of 0.5 and Lmax (A) to a value of 1.2 when A is MMA; ⁇ LmZn (A) corresponds to a value of 0.6 and Lmax (A) to a value of 3.2 when A is THFMA;
  • ⁇ LmZn (A) corresponds to a value of 0.5 and Lmax (A) to a value of 1.7 if A is CHMA;
  • ⁇ LmZn (A) corresponds to a value of 0.5 and Lmax (A) to a value of 1.5 if A is IBMA;
  • ⁇ LmZn (A) is a value of 0.5 and Lmax (A) is a value of 2 if A is TMCHMA. In particular, correspond
  • ⁇ LmZn (A) has a value of 0.6, preferably 0.8, and Lmax (A) has a value of 1.1, preferably 1, when A is MMA; ⁇ LmZn (A) has a value of 1, preferably 1.5, and Lmax (A) a
  • ⁇ Lmax (A) is 1.5 if A is CHMA;
  • ⁇ Lmax (A) has a value of 1.3, preferably 1, if A is IBMA;
  • ⁇ Lmax (A) has a value of 1.5, preferably 1, if A is TMCHMA.
  • the value w (A) represents the proportion of the respective monomer A in this sum ⁇ (A), so that the sum of all
  • a composition comprising a mixture of two monomers A, namely 10% by weight MMA and 15% by weight CHMA, is used.
  • the sum of the proportions of the monomers A, that is to say ⁇ (A), is accordingly 25% by weight.
  • the sum of all weight parts ⁇ (w (A)) consequently always corresponds to a value of 1.
  • ⁇ 0.5 and 1.2 in particular between 0.6 and 1.1, preferably between 0.8 and 1, when A is MMA; - 0.6 and 3.2, in particular between 1 and 2.6, preferably between
  • ⁇ 0.5 and 1.5 in particular between 0.5 and 1.3, preferably between 0.5 and 1, when A is IBMA;
  • ⁇ 0.5 and 2 in particular between 0.5 and 1.5, preferably between 0.5 and 1, when A is TMCHMA.
  • Adhesive properties but only a very low flexibility. As a result, it is unsuitable for the bonding of materials with different coefficients of linear expansion, in particular for the bonding of glass with PVC and / or aluminum.
  • Substance names beginning with "poly”, such as, for example, polyisocyanate, polyurethane, polyester or polyol, in the present document refer to substances which formally contain two or more of the functional groups occurring in their name per molecule.
  • polymer in the present document comprises, on the one hand, a collective of chemically uniform, but different in terms of degree of polymerization, molecular weight and chain length macromolecules, which was prepared by a polyreaction (polymerization, polyaddition, polycondensation) Derivatives of such a collective of macromolecules from polyreactions, ie compounds which have been obtained by reactions, such as additions or substitutions, of functional groups on predetermined macromolecules and which may be chemically uniform or chemically non-uniform Prepolymers, that is to say reactive oligomeric pre-adducts whose functional groups are involved in the synthesis of macromolecules
  • polymeric polyol in the present document comprises any polymer according to the preceding definition which has more than one hydroxyl group e has. Accordingly, the term “polymeric diol” includes any polymer having exactly two hydroxyl groups.
  • polyurethane polymer encompasses all polymers which are prepared by the so-called diisocyanate-polyaddition process, including those polymers which are almost or completely free of urethane groups.
  • molecular weight is meant in this document always the number average molecular weight M n .
  • the elastomer C of the formula (I) preferably has an average molecular weight of from 1,000 to 40,000 g / mol, in particular from 1,000 to 30,000 g / mol, preferably from 1,000 to 20,000 g / mol , on.
  • the radical X is a polymeric polyol after removal of two OH groups, this polymeric polyol in particular being a polyalkylene polyol, a polyoxyalkylene polyol or a polyurethane polyurethane; a polyhydroxy-functional ethylene-propylene, ethylene-butylene or ethylene-propylene-diene copolymer; a polyhydroxy-functional copolymer of dienes such as 1,3-butadiene or diene mixtures and vinyl monomers such as styrene, acrylonitrile or isobutylene; a polyhydroxy-functional polybutadiene polyol; a polyhydroxy-functional acrylonitrile / butadiene copolymer; or a polysiloxane polyol.
  • Polyhydroxy-terminated acrylonitrile / butadiene copolymers are typically formed from carboxyl-terminated acrylonitrile / butadiene copolymers, which Performance for example under the name of Hycar ® CTBN from Emerald Performance Materials, LLC, USA, are commercially available, and epoxides or aminoalcohols.
  • Suitable elastomers C of the formula (I) are for example commercially available from Kraton Polymers, USA, or performance under the trade names Hycar ® and VTB Hycar VTBNX ® by the company Emerald Performance Materials, LLC, USA.
  • the polymeric polyol is a polymeric diol PD.
  • the elastomer C of the formula (I) is preferably a polyurethane (meth) acrylate.
  • Such compounds are typically preparable from the reaction of at least one diol D with at least one diisocyanate and a (meth) acrylic acid, a (meth) acrylamide or a (meth) acrylic acid ester which has a hydroxyl group.
  • this reaction can take place in that the diol D and the diisocyanate with conventional methods, for example at temperatures from 50 0 C to 100 0 C, optionally using suitable catalysts, be reacted, whereby it must be ensured, the NCO groups are present in stoichiometric excess relative to the OH groups.
  • the isocyanate group-terminated polyurethane polymer resulting from this reaction is then reacted with a (meth) acrylic acid, a (meth) acrylamide or with a (meth) acrylic ester which has a hydroxyl group, in particular with a hydroxyalkyl (meth) acrylate such as hydroxypropyl acrylate (HPA).
  • a hydroxyalkyl (meth) acrylate such as hydroxypropyl acrylate (HPA).
  • Hydroxypropyl methacrylate HPMA
  • HBA hydroxybutyl acrylate
  • HBMA hydroxybutyl methacrylate
  • HEMA hydroxyethyl methacrylate
  • a monohydroxypoly (meth) acrylate of a polyol preferably from glycerol or trimethylolpropane, to a polyurethane (meth) - acrylate, reacted.
  • the diol D can be reacted with the diisocyanate, wherein the OH groups are present in stoichiometric excess over the NCO groups.
  • the hydroxyl group-terminated polyurethane polymer resulting from this reaction can be esterified with a (meth) acrylic acid to give the elastomer C of formula (I).
  • a further process for preparing the elastomer C is, in a first step, the (meth) acrylic acid, the (meth) acrylamide or the (meth) acrylic ester which has a hydroxyl group, in particular hydroxyalkyl (meth) acrylate such as hydroxypropyl acrylate (HPA ), Hydroxypropyl methacrylate (HPMA), hydroxybutyl acrylate (HBA) or hydroxybutyl methacrylate (HBMA), preferably hydroxyethyl acrylate (HEA) or hydroxyethyl methacrylate (HEMA), or a monohydroxypoly (meth) acrylate of a polyol, preferably of glycerol or trimethylolpropane, with at least one diisocyanate, which is used in an amount such that the NCO groups are in excess of the OH groups.
  • HPA hydroxypropyl acrylate
  • HPMA Hydroxypropyl methacrylate
  • HBA hydroxybut
  • the resulting isocyanate group-having intermediate is reacted with at least one diol D to form the elastomer C of formula (I).
  • the preparation of the elastomer C of the formula (I) by esterification of a (meth) acrylic acid with a diol D, wherein the
  • the partially esterified diol D reacts with a diisocyanate to the elastomer C of the formula (I).
  • Preferred diols D are polyoxyalkylenediols, also called “polyetherdiols", polyesterdiols, polycarbonatediols and mixtures thereof
  • the most preferred diols are polyoxyethylenediols, polyoxypropylenediols or polyoxybutylenediols.
  • the polyoxyalkylene diols may have different levels of unsaturation (measured according to ASTM D-2849-69 and expressed in milliequivalents of unsaturation per gram of polyol (mEq / g)).
  • Those with a low degree of unsaturation are prepared, for example, by means of so-called double metal cyanide complex catalysts (DMC catalysts), those having a higher degree of unsaturation are prepared, for example, with the aid of anionic catalysts such as NaOH, KOH, CsOH or alkali metal alkoxides.
  • DMC catalysts double metal cyanide complex catalysts
  • polyoxyalkylene diols having a low level of unsaturation in particular of less than 0.01 meq / g, is preferred for diols with a molecular weight of> 2000 g / mol.
  • diisocyanates are suitable as diisocyanates.
  • mention may be made of 1,6-hexamethylene diisocyanate (HDI), 2-methylpentamethylene-1,5-diisocyanate, 2,2,4- and 2,4,4-trimethyl-1,6-hexamethylene diisocyanate (TMDI), 1, 12-dodecamethylene diisocyanate, lysine and Lysinesterdiiso- cyanat, cyclohexane-1, 3-diisocyanate, cyclohexane-1, 4-diisocyanate, 1-isocyanato-S ⁇ - trimethyl- ⁇ -isocyanatomethyl-cyclohexane ( isophorone diisocyanate or IPDI), perhydro-2,4'-diphenylmethane diisocyanate and perhydro-4,4'-diphenylmethane diisocyanate, 1,4-diisocyanato-2,2,6
  • Preferred diisocyanate is 1-isocyanato-3,3,5-trimethyl-5-isocyanato-methyl-cyclohexane (IPDI).
  • the composition described contains tetrahydrofurfuryl methacrylate (THFMA) as monomer A, ethyl hexyl acrylate (EHA) or maleic acid diallyl ester (MADAE) as comonomer B, and polyurethane (meth) acrylate as elastomer C.
  • THFMA tetrahydrofurfuryl methacrylate
  • EHA ethyl hexyl acrylate
  • MADAE maleic acid diallyl ester
  • polyurethane (meth) acrylate as elastomer C.
  • the composition may additionally contain at least one adhesion promoter, in particular a metal (meth) acrylate or a (meth) acrylate of the formula (II).
  • at least one adhesion promoter in particular a metal (meth) acrylate or a (meth) acrylate of the formula (II).
  • the radical R ' is either a hydrogen atom or a methyl group
  • n is a value of 1 to 15, in particular from 1 to 5, preferably from 1 to 3.
  • m is a value of 1 to 3 and p is a value of 3 minus m.
  • Preferred metal (meth) acrylates are metal (meth) acrylates of
  • Calcium, magnesium or zinc which have a hydroxyl group and / or (meth) - acrylic acid or (meth) acrylate as a ligand or anion.
  • Particularly preferred metal (meth) acrylates are zinc (meth) acrylate, calcium (meth) acrylate, Zn (OH) (meth) acrylate and magnesium (meth) acrylate.
  • Preferred (meth) acrylates of the formula (II) are 2-methacryloyloxyethyl phosphate, bis (2-methacryloyloxyethyl) phosphate and also tris (2-methacryloyloxyethyl) phosphate and mixtures thereof.
  • the proportion of the optional adhesion promoter to the total composition is preferably between 0.01 and 5 wt .-%, in particular between 0.5 and 4 wt .-%.
  • composition may additionally contain at least one core-shell polymer.
  • Core-shell polymers consist of an elastic core polymer (core) and a rigid shell polymer (shell).
  • Particularly suitable core-shell polymers consist of a rigid shell of a rigid thermoplastic polymer grafted onto a core of crosslinked elastic acrylate or butadiene polymer.
  • Particularly suitable core-shell polymers are those which swell in the monomer A and / or in the comonomer B, but do not dissolve therein.
  • Preferred core-shell polymers are the so-called MBS polymers commercially for example under the trade name Clearstrength ® from Arkema Inc., USA, or Paraloid ® from Rohm and Haas, USA, is.
  • the core-shell polymers are preferably used in an amount of from 0.01 to 30% by weight, in particular from 10 to 20% by weight, based on the total composition.
  • the composition may additionally contain at least one catalyst, in particular a tertiary amine, a transition metal salt or a transition metal complex.
  • a tertiary amine such suitable tertiary amines are N, N-dimethylaniline, N, N-diethylaniline, N, N-dimethyl-p-toluidine, N, N-diethyl-p-toluidine, N-methyl-N-hydroxyethyl-p-toluidine, N, N-O / s (2-hydroxyethyl) -p-toluidine and also alkoxylated N, N-ib / s (hydroxyethyl) -p-toluidines, N-ethoxylated p-toluidine, N-alkylmorpholine and mixtures thereof .
  • Transition metal salts and transition metal complexes are, for example, salts and complexes of cobalt, nickel, copper, manganese or vanadium.
  • the catalysts are usually used in an amount of 0.01 to 2.5 wt .-%, in particular from 0.1 to 2 wt .-%, based on the composition.
  • the composition may additionally contain at least one filler.
  • Particularly suitable are natural, ground or precipitated calcium carbonates (chalks), which are optionally coated with fatty acids, in particular stearates, montmorillonites, bentonites, barium sulfate (BaSO 4 , also called barite or barite), calcined kaolins, quartz powder, aluminum oxides, Aluminum hydroxides, silicic acids, in particular fumed silicas, modified castor oil derivatives and polymer powder or polymer fibers.
  • fatty acids in particular stearates, montmorillonites, bentonites, barium sulfate (BaSO 4 , also called barite or barite)
  • BaSO 4 barium sulfate
  • calcined kaolins quartz powder, aluminum oxides, Aluminum hydro
  • the filler is usually used in an amount of 0.01 to 30 wt .-%, in particular from 10 to 30 wt .-%, preferably 15 to 20 wt .-%, based on the total composition.
  • composition may additionally at least one
  • Free radical generator included. Suitable free-radical formers are, in particular, molecules which under the influence of heat or electromagnetic radiation form radicals, which then lead to the polymerization of the composition.
  • Particularly suitable radical generators are thermally activatable free-radical formers and photoinitiators.
  • thermally activatable free-radical formers are those which are still sufficiently stable at room temperature but already form radicals at a slightly elevated temperature.
  • such is one
  • Free radical generator a peroxide, a perester or a hydroperoxide. Preference is given to organic peroxides. Most preferred is dibenzoyl peroxide.
  • Photoinitiators are free-radical formers which form radicals under the influence of electromagnetic radiation. Particularly suitable is a photoinitiator which forms free radicals upon irradiation with an electromagnetic radiation of the wavelength of 230 nm to 400 nm and is liquid at room temperature.
  • the photoinitiator is particularly preferably selected from the group consisting of ⁇ -hydroxyketones, phenylglyoxylates, monoacylphosphines, diacylphosphines, phosphine oxides and mixtures thereof, in particular 1-6 Hydroxy-cyclohexyl-phenyl-ketone, benzophenone, 2-hydroxy-2-methyl-1-phenyl-propanone, methyl-phenyl-glyoxylate, oxy-phenyl-acetic acid 2- [2-oxo-2-phenyl-acetoxy- ethoxy] ethyl ester, oxy-phenyl-acetic acid 2- [2-ethoxyethoxy] - ethyl ester, diphenyl (2,4,6-trimethylbenzoyl) phosphine oxide, phenylbis (2,4,6-trimethylbenzoyl) phosphine oxide and mixtures thereof , Such photoinitiators are available commercially for example from the product
  • composition may, if appropriate, additionally
  • Such additional constituents are toughness modifiers, dyes, pigments, inhibitors, UV and heat stabilizers, metal oxides, antistatic agents, flame retardants, biocides, plasticizers, waxes, leveling agents, adhesion promoters, thixotropic agents, spacers and other common raw materials and additives known to the person skilled in the art.
  • the composition is preferably a two-component composition, wherein two components K1 and K2 are stored separately from each other until application.
  • a first component K1 includes in particular those ingredients of the described composition which have radically polymerizable groups.
  • a second component K2 includes in particular the radical formers.
  • other constituents in particular those which impair the storage stability of the composition by reaction with one another, can also be stored separately.
  • component K1 comprises the components monomers, elastomers, core-shell polymers, catalysts, adhesion promoters, pigments and fillers
  • component K2 comprises the radical initiator, pigments and fillers.
  • the mixing ratio of K1 to K2 is in particular in the range of 1: 1 to 10: 1. In certain cases, it may be beneficial to use the two components
  • the mixing quality can be checked when mixing the components, and mixing errors can be detected at an early stage. Likewise, this measure can qualitatively check whether the intended mixing ratio has been observed.
  • Another aspect of the invention relates to a package which consists of a packaging and a packaged product.
  • the packaging in this case has two separate chambers.
  • the packaged product is a two-component free-radically curing composition consisting of a first component K1 and a second component KZ, as just described.
  • the components K1 is in this case in one chamber and the component K2 is present in the other chamber of the package.
  • the package forms in particular a unit in which the two
  • Chambers are held together or bound directly to each other.
  • the partition between the chambers may be, for example, a film or a breakable layer or one or two closures which seal an opening.
  • the packaging is a double cartridge.
  • FIG 1 and Figure 2 show schematic representations of such double cartridges, which are in particular as a twin cartridge 1 or as a coaxial cartridge 2 in cross-section ( Figure 1a and 2a) and in longitudinal section ( Figure 1b and 2b).
  • Such cartridge packages are prior art for bicomponent compositions.
  • twin cartridge 1 ( Figure 1) are two adjacent, possibly by webs or a seam or a sheath, for example by a film, longitudinally interconnected, tubular container with rigid chamber walls 5 are present, which on one side with a displaceable Piston 4 are closed and on the other side each have a closed or closable opening 6, which are typically arranged together in a mouthpiece are.
  • This mouthpiece has a thread 3, to which typically a static mixer (not shown) can be screwed.
  • the coaxial cartridge 2 corresponds to the twin cartridge with the difference that the tubular containers are not adjacent to each other but arranged inside each other and thus results in a tube-in-tube arrangement.
  • a further possibility of packaging forms a multi-chamber tubular bag or a multi-chamber tubular bag with adapter, as disclosed, for example, in WO 01/44074 A1, and the contents of which are thus included as subject matter of the present invention.
  • the mixing of the two components K1 and K2 takes place with the aid of a static mixer, which can be placed on the packaging preferably used for this method with two chambers.
  • the two components K1 and K2 are typically kept separate from one another in barrels or hobbocks and during application, for example by means of gear pumps, pressed out and mixed.
  • the composition can be applied to a substrate by hand or in an automated process by means of robots.
  • the invention comprises the use of a composition, as described above, as an adhesive or sealant or for the production of coatings.
  • the invention comprises the use of the composition for the bonding of materials having different coefficients of linear expansion, preferably for the bonding of glass and ceramic substrates with plastics and / or metals.
  • Particularly suitable is the composition for bonding materials whose linear thermal expansion coefficients are in a ratio of ⁇ 2: 1 to each other.
  • the linear thermal expansion coefficients of the substrates to be bonded are in a ratio of> 3: 1 to each other when the substrates to be bonded glass or a ceramic substrate and a metal; and in a ratio of> 8: 1, when the substrates to be bonded glass or a ceramic substrate and a plastic are.
  • the linear thermal expansion coefficients in a ratio of ⁇ 10'0OO: 1, preferably in a ratio of ⁇ 100: 1, to each other.
  • the invention comprises the use of a composition, as described above, as an adhesive or sealant in window construction, where glass is bonded to plastics and / or metals, in particular polyvinyl chloride (PVC) and / or aluminum.
  • a composition as described above, as an adhesive or sealant in window construction, where glass is bonded to plastics and / or metals, in particular polyvinyl chloride (PVC) and / or aluminum.
  • PVC polyvinyl chloride
  • the term aluminum in this case also alloys of aluminum, in particular with copper, magnesium, silicon, manganese and / or zinc, to understand.
  • the aluminum may be subjected to surface treatment prior to application of the composition.
  • the aluminum controlled to oxidation, for example by the electrolytic oxidation of aluminum (ELOXAL ).
  • ELOXAL electrolytic oxidation of aluminum
  • Another method of surface treatment is the so-called enamelling, in which other inorganic layers, mainly of oxides and silicates, are applied to the aluminum.
  • composition according to the invention as a sealant for hem flange bonds.
  • the substrate on the surface of which the mixed composition is applied may have been previously treated with suitable pretreatment agents or cleaners. It is particularly suitable pretreatment or cleaning the substrates with Sika ® Cleaner P or Sika ® ADPrep which are commercially available from Sika Switzerland AG.
  • compositions of the invention may be useful in certain cases, but compositions of the invention have proven to be particularly advantageous because they can be primerless applied to numerous substrates, especially glass, PVC and aluminum without loss of adhesion.
  • the invention comprises a method of bonding substrates S1 and S2 comprising the steps of i) applying a composition according to the preceding
  • step I) of the at least partial mixing of the two components can take place.
  • the invention comprises a method of sealing or coating a substrate S1 comprising the steps i ") applying a composition according to the preceding
  • step I of the at least partial mixing of the two components can take place.
  • the present invention comprises a cured composition obtained from a previously described composition by a curing process.
  • the composition is characterized by the fact that it shows no viscoelastic behavior and thus that under pressure is no, or almost no, plastic deformation of the composition.
  • the invention includes articles which have been bonded or sealed by a previously described method. These articles are preferably a building, in particular a building construction or civil engineering, or an industrial good or a consumer good, in particular a window, a household machine, a tool or a means of transport, in particular a vehicle on land or water, preferably an automobile, a bus, a truck, a train or a ship.
  • Such articles are preferably also add-on parts of industrial goods or means of transport, in particular also module parts, which are used on the production line as modules and in particular are glued or glued on.
  • these prefabricated attachments are used in transport construction.
  • such attachments are cabs of trucks or locomotives or sunroofs of automobiles.
  • these articles are windows and doors, as used in buildings.
  • FIG. 3 shows a schematic representation of a glued window or glued door in partial cross-section.
  • the frame 10 which consists of plastic or of a metal, in particular PVC or aluminum, and may have a sealing lip 9, glued to an insulating glass pane.
  • Insulating glass panes typically consist of an inner window pane 11 and an outer window pane 11 'with a spacer 12 located therebetween and an insulating glass seal 13.
  • the adhesive 8 is thereby applied, in particular, between the inner window pane 11 and the frame 10.
  • the front side of the insulating glass pane 7 is also glued to the frame 10. In this case, there is adhesive between the frame 10 and the end face of the insulating glass pane. 7 Examples
  • the elastomer C1 was prepared as follows:
  • compositions were prepared: As component K1, those listed in Tables 1 to 3 were added
  • component K2 50% by weight of dibenzoyl peroxide (20% strength) in plasticizer, 47% by weight of chalk, 2.5% by weight of thixotropic agent and 0.5% by weight of a pigment were mixed together in a dissolver.
  • the prepared components K1 and K2 were filled in the separate chambers of coaxial cartridges and used in a volume ratio K1: K2 of 10: 1.
  • Elongation at break “Elong.”
  • E-mod modulus of elasticity
  • Elastic modulus is reported in the range of 0.5 to 8% elongation.
  • the Tensile Shear Strength (“TSS”) was determined on the basis of ISO 4587 / DIN EN 1465 on a tractor Zwick / Roell Z005, whereby in each case two identical substrates were glued together (adhesive surface: 12x25 mm, layer thickness: 1.5 mm, measuring speed : 10 mm / min; substrates: float glass, PVC and aluminum; temperature: 23 ° C (unless otherwise specified)).
  • PVC slats 15 were at a temperature of 23 0 C as shown in Figure 4 (top) bonded with glass sheets 14 in the longitudinal direction.
  • the adhesive 8 was applied in a layer thickness of 5 mm to the PVC lamella between two foam adhesive tape webs, which were attached as spacers. After the adhesive was cured for 24 hours in a standard atmosphere, the laminated body prepared for 12 hours at a temperature of -20 0 C was exposed and in Figure 4 (below) are shown.
  • the maximum deflection was measured in the center of the body, ie in the range of 50 cm +/- 2 cm from one end of the body, at the point of maximum deflection 16.
  • Figure 1 shows schematically a twin cartridge (1) in cross section (Figure 1a) and in longitudinal section (Figure 1b).
  • Figure 2 shows schematically a coaxial cartridge (2) in cross-section (Figure 2a) and in longitudinal section (Figure 2b).
  • FIG. 3 schematically shows a partial cross section through a window or a door.
  • Figure 4 shows schematically a glass pane (14) which is glued to a PVC lamella (15) and the point with a maximum deflection (16).

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention concerne des compositions de (méth)acrylate élastiques qui comprennent au moins un monomère A, un comonomère B et un élastomère C. De telles compositions sont appropriées pour le collage, le colmatage et pour la fabrication de revêtements. Les compositions selon l'invention s'utilisent notamment pour le collage de substrats avec différents coefficients d'expansion thermique linéaires, pour lequel un effet de type bimétal est observé en cas de fluctuations de la température. Les compositions s'utilisent de préférence pour le collage de verre avec du chlorure de polyvinyle (PVC) et/ou de l'aluminium.
EP08708185A 2007-06-14 2008-01-25 Composition de (méth)acrylate élastique Withdrawn EP2158236A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP08708185A EP2158236A1 (fr) 2007-06-14 2008-01-25 Composition de (méth)acrylate élastique

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP07110298A EP2003153A1 (fr) 2007-06-14 2007-06-14 Composition (méth)acrylate élastique
PCT/EP2008/050846 WO2008151849A1 (fr) 2007-06-14 2008-01-25 Composition de (méth)acrylate élastique
EP08708185A EP2158236A1 (fr) 2007-06-14 2008-01-25 Composition de (méth)acrylate élastique

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Publication Number Publication Date
EP2158236A1 true EP2158236A1 (fr) 2010-03-03

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EP07110298A Withdrawn EP2003153A1 (fr) 2007-06-14 2007-06-14 Composition (méth)acrylate élastique
EP08708185A Withdrawn EP2158236A1 (fr) 2007-06-14 2008-01-25 Composition de (méth)acrylate élastique

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EP07110298A Withdrawn EP2003153A1 (fr) 2007-06-14 2007-06-14 Composition (méth)acrylate élastique

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EP (2) EP2003153A1 (fr)
WO (1) WO2008151849A1 (fr)

Families Citing this family (8)

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Publication number Priority date Publication date Assignee Title
JP5402225B2 (ja) * 2008-11-26 2014-01-29 Ｊｓｒ株式会社 電線止水材用キット、電線止水材、止水部材、止水処理された電線および止水処理方法
GB201006427D0 (en) 2010-02-26 2010-06-02 Scott Bader Co Methacrylate-based adhesive compositions
EP2650316A1 (fr) 2012-04-10 2013-10-16 Sika Technology AG Compositions radicalement durcissables adaptées au collage de PVC comprenant du plastifiant
CN105254817B (zh) * 2015-11-26 2018-09-11 淄博华星助剂有限公司 核壳结构丙烯酸酯类发泡调节剂的制备方法
CN108219620A (zh) * 2016-12-09 2018-06-29 罗门哈斯公司 具有橡实形态的聚合物粒子的水性分散液
AU2022292055A1 (en) * 2021-06-15 2023-12-21 Sika Technology Ag (meth)acrylate composition with improved low-temperature elasticity
WO2023104485A1 (fr) 2021-12-09 2023-06-15 Sika Technology Ag Composition élastique de (méth)acrylate présentant une adhérence améliorée sur des substrats huileux
WO2023194422A1 (fr) 2022-04-07 2023-10-12 Sika Technology Ag Adhésif à base de (méth)acrylate pour liaison d'angle de coin

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3994764A (en) 1975-06-13 1976-11-30 Pratt & Lambert, Inc. Adhesive compositions
US4439600A (en) 1983-06-03 1984-03-27 Loctite Corporation Cure to elastomers compositions
US4769419A (en) 1986-12-01 1988-09-06 Dawdy Terrance H Modified structural adhesives
PT1246765E (pt) 1999-12-17 2005-04-29 Sika Schweiz Ag Adaptador, dispositivo e metodo para a remocao de materiais de sacos tubulares multi-camaras, utilizacao do adaptador e embalagem de sacos tubulares
EP1239016A1 (fr) 2001-03-08 2002-09-11 Sika AG, vorm. Kaspar Winkler & Co. Compositions methacryliques élastiques adhésives
EP1239015A1 (fr) * 2001-03-08 2002-09-11 Sika AG, vorm. Kaspar Winkler & Co. Compositions d'adhésifs methacryliques aisées à préparer
US6433091B1 (en) * 2001-05-10 2002-08-13 Henkel Loctite Corporation Adhesive composition
EP1609831B1 (fr) * 2004-06-23 2006-08-16 Sika Technology AG Adhesif (meth)acrylique ayant une faible odeur et une haute résistance à l'impact

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2008151849A1 *

Also Published As

Publication number Publication date
EP2003153A1 (fr) 2008-12-17
WO2008151849A1 (fr) 2008-12-18

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