EP3024797A1 - Mortiers de résines de réaction, système de mortier à plusieurs composants et leur utilisation - Google Patents

Mortiers de résines de réaction, système de mortier à plusieurs composants et leur utilisation

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Publication number
EP3024797A1
EP3024797A1 EP14741911.3A EP14741911A EP3024797A1 EP 3024797 A1 EP3024797 A1 EP 3024797A1 EP 14741911 A EP14741911 A EP 14741911A EP 3024797 A1 EP3024797 A1 EP 3024797A1
Authority
EP
European Patent Office
Prior art keywords
mortar
resin
component
reaction resin
reaction
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Withdrawn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
EP14741911.3A
Other languages
German (de)
English (en)
Inventor
Thomas Bürgel
Monika Mönch
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.)
Hilti AG
Original Assignee
Hilti 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 Hilti AG filed Critical Hilti AG
Priority to EP14741911.3A priority Critical patent/EP3024797A1/fr
Publication of EP3024797A1 publication Critical patent/EP3024797A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B26/00—Compositions of mortars, concrete or artificial stone, containing only organic binders, e.g. polymer or resin concrete
    • C04B26/02—Macromolecular compounds
    • C04B26/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C04B26/06—Acrylates
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
    • C04B24/008—Aldehydes, ketones
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B40/00—Processes, in general, for influencing or modifying the properties of mortars, concrete or artificial stone compositions, e.g. their setting or hardening ability
    • C04B40/06—Inhibiting the setting, e.g. mortars of the deferred action type containing water in breakable containers ; Inhibiting the action of active ingredients
    • C04B40/0666—Chemical plugs based on hydraulic hardening materials
    • E—FIXED CONSTRUCTIONS
    • E21—EARTH OR ROCK DRILLING; MINING
    • E21B—EARTH OR ROCK DRILLING; OBTAINING OIL, GAS, WATER, SOLUBLE OR MELTABLE MATERIALS OR A SLURRY OF MINERALS FROM WELLS
    • E21B33/00—Sealing or packing boreholes or wells
    • E21B33/10—Sealing or packing boreholes or wells in the borehole
    • E21B33/13—Methods or devices for cementing, for plugging holes, crevices or the like
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B2111/00—Mortars, concrete or artificial stone or mixtures to prepare them, characterised by specific function, property or use
    • C04B2111/00474—Uses not provided for elsewhere in C04B2111/00
    • C04B2111/00715—Uses not provided for elsewhere in C04B2111/00 for fixing bolts or the like
    • 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
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • 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
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/106—Esters of polycondensation macromers
    • C08F222/1065—Esters of polycondensation macromers of alcohol terminated (poly)urethanes, e.g. urethane(meth)acrylates

Definitions

  • the present invention relates to a reaction resin mortar comprising a resin mixture containing at least one free-radically polymerizable compound, at least one reactive diluent and at least one polymerization inhibitor, wherein the resin mixture is adjusted to a certain viscosity, a two- or multi-component mortar system containing the reaction resin mortar and the use of Construction purposes, in particular for chemical attachment.
  • Two-component mortar compositions with a curable resin component containing at least one free-radically polymerizable resin, fillers, accelerators, stabilizers and optionally other conventional mortar constituents, and a reaction inhibiting separately arranged hardener component containing at least one peroxide and their use for construction purposes are known.
  • Two-component mortar compositions of this type are used, for example, as injection mortars for the chemical anchoring of fasteners, preferably metal elements, in various substrates, preferably mineral substrates, such as in particular buildings made of brick, concrete or natural stone.
  • the necessary for fastening the anchoring means boreholes are introduced into the mineral substrate, after which the curable resin component with the Hardener component of the two-component mortar composition is mixed and introduced into the borehole, whereupon the anchoring means to be fastened is introduced and adjusted and hardens the mortar composition.
  • the applicant distributes injection mortars in the form of fast-curing systems, which has a hybrid system of a radical-curing methacrylate resin and a hydraulically setting cement, which results after processing in the borehole extremely durable plastic.
  • the mortar masses are either declared as universal mortar or the mortar mass is formulated in a coordinated manner to the substrate.
  • Acetoacetoxyalkyl (meth) acrylates such as the acetoacetoxyethyl methacrylate (DE 41 31 457 A1), their combination (DE 10 2004 035 567 B4) or additionally with alkyl (meth) acrylates (DE 10 2009 043 792 A1) could not significantly improve the performance.
  • the object of the invention is therefore to provide a reaction resin mortar with improved performance when used in mineral substrates, in particular masonry.
  • the inventors were able to surprisingly find out that the viscosity of the resin mixture has a noticeable influence on the performance of a mortar composition.
  • the load values increase with increasing viscosity, whereby the viscosity is limited to the extent that after the formulation of a two- or multi-component system, the masses still have to be processable. In particular, the masses must still be deployed with a manual dispenser.
  • reaction mixture means a mixture of the reaction mixture of the resin preparation containing the radically polymerizable compound, optionally one Catalyst for the preparation of the compound, reactive diluents, and stabilizers and optionally accelerators and optionally further reactive diluents;
  • reaction resin mortar means a mixture of resin mixture and inorganic and / or organic aggregates
  • Hardening agent Substances which cause the polymerization (hardening) of the base resin "Cures” a mixture of curing agent and inorganic and / or organic additives;
  • “Accelerator” means a compound capable of accelerating the polymerization reaction (cure) and serving to accelerate the formation of the radical initiator;
  • Polymerization inhibitor also referred to herein for short as “inhibitor”, a compound capable of inhibiting the polymerization reaction (cure) which serves to promote the polymerization reaction and thus undesired premature polymerization of the radically polymerizable compound
  • Avoid compound during storage (often referred to as a stabilizer) and which serves to delay the start of the polymerization reaction immediately after the addition of the curing agent;
  • the inhibitor is usually used in such small amounts that the gelling time is not affected;
  • the inhibitor is usually used in amounts such that the gelation time is influenced;
  • Reactive diluents are liquid or low-viscosity free-radically polymerizable compounds which dilute the resin mixture and thereby add to the latter
  • “Mortar composition” means the formulation obtained by mixing the reaction resin mortar with the hardening agent and as such can be used directly for chemical attachment;
  • Tro-component system means a system comprising two separate components, generally a resin component and a hardener component, such that curing of the reaction resin mortar is possible only after mixing the two
  • Multicomponent system means a system comprising three or more separately stored components so that curing of the reaction resin mortar does not take place until all the components have been mixed;
  • the inventors have surprisingly found that with a resin mixture whose viscosity is between 200 and 800 mPa ⁇ s, preferably between 300 and 500 mPa ⁇ s measured according to DIN EN ISO 2884 with a rheometer RS 600 from Haake, Düsseldorf; Measuring geometry plate cone 0 60 mm, 1 ° titanium (C60 / 1 0 Ti), gap 0.052 mm at 23 ° C and a shear rate of 150 s ⁇ ⁇ is set, the performance of a mortar mass in masonry, especially in brick significantly increased can.
  • a first subject of the invention is therefore a reaction resin mortar comprising a resin mixture containing at least one free-radically polymerizable compound, at least one reactive diluent and at least one inhibitor, and organic and / or inorganic aggregates, characterized in that the resin mixture has a viscosity in the range between 200 and 800 mPa-s, preferably between 300 and 500 mPa-s, measured according to DIN EN ISO 2884 at 23 ° C, has.
  • the solvents may be inert to the reaction system or, what is preferred, participate in the polymerization during curing, so-called reactive diluents.
  • the reactive diluents can be added in an amount of 90 to 10% by weight, preferably 70 to 30% by weight, based on the resin mixture, the amount being selected to adjust the resin mixture to the desired viscosity.
  • the resin mixture contains as reactive diluents a (meth) acrylic acid ester, with particular preference the (meth) acrylic acid ester being selected from the group consisting of hydroxypropyl (meth) acrylate, propanediol-1,3-di (meth) acrylate, butanediol-1, 3-di (meth) acrylate, trimethylolpropane tri (meth) acrylate, 2-ethylhexyl (meth) acrylate, phenylethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, ethyltriglycol (meth) acrylate, N, N-dimethylaminoethyl (meth) acrylate , N, N
  • the inventors were also able to find out that the choice of reactive diluent has a further positive influence on the performance, in particular on the failure loads in the brick. Quite unexpectedly and surprisingly, it has been found that the performance of a reaction resin mortar in bricks can be further increased when using 1,3-dicarbonyl compounds as reactive diluents.
  • the reactive diluent is 1, 3-dicarbonyl compounds of the general formula (I)
  • R is a straight-chain or branched, optionally substituted, C 1 -C 6 -alkyl group, preferably C 1 -C 6 -alkyl group;
  • R 2 is hydrogen, a straight-chain or branched, optionally substituted, C 1 -C 6 -alkyl group, preferably C 1 -C 2 -alkyl group, or a C 1 -C 6 -alkoxy group, preferably C 1 -C 2 -alkoxy group, or together with R 3 represents an optionally substituted one forms a five- or six-membered aliphatic ring which optionally comprises heteroatoms in or on the ring; or the general formula (III)
  • R 4 denotes a dihydric or higher alcohol (hereinafter also referred to as polyol compound),
  • x means a number between 1 and 6,
  • R and R 2 have the same meaning as defined above, wherein R is particularly preferably a methyl group and R 2 is particularly preferably hydrogen.
  • Suitable dihydric or higher alcohols include, for example, alkanediols, alkylene glycols such as ethylene glycol or propylene glycol, glycerols, sugars, pentaerythritols, polyhydric derivatives or mixtures thereof.
  • higher alcohols are neopentyl glycol, trimethylolpropane, ethylene glycol and polyethylene glycol, propylene glycol and polypropylene glycol, butanediol, pentanediol, hexanediol, tricyclodecanedimethylol, 2,2,4-trimethyl-1,3-pentanediol, bisphenol A, Cyclohexanedimethanol, castor oil and their alkoxylated and / or propoxylated derivatives.
  • the compound of the formula (III) is selected from acetoacetates of optionally mono- or poly-ethoxylated and propoxylated diols, triols and polyols, for example ethylene glycol monoacetoacetate, ethylene glycol diacetoacetate, 1, 2
  • Trimethylol propane Glycerinmonoacetoacetat, Glycerindiaceoacetat, Glycerintriacetoacetat, Pentaerythritoltetraacetoacetat, Pentaerythritolmonoacetoacetat, Pentaerythritoldiacetoacetat, Pentaerythritoltriacetoacetat, Pentaerythritoltetraacetoacetat, Dipentaerythritolmonoacetoacetat, Dipentaerythritoldiacetoacetat, Dipentaerythritoltriacetoacetat, Dipentaerythritoltertaacetoacetat, Dipentaerythritolpentaacetoacetat or Dipentaerythritolhexaacetoacetat.
  • the compound of the formula (I) is a compound of the formula (IV)
  • n 1, 2 or 3, preferably 1 or 2
  • X is O, S, or NR 5 , preferably O, in which R 5 is hydrogen or an optionally substituted, alkyl, cycloalkyl , Aryl or aralkyl group.
  • n is preferably 1, X is O and R is OR 6 , in which R 6 is an optionally substituted alkyl group, particularly preferably methyl group.
  • the compound of formula (IV) is ⁇ -acetyl- ⁇ -butyrolactone (ABL).
  • the at least one reactive diluent is selected from the group consisting of acetylacetone, 2- (acetoacetoxy) ethyl methacrylate, triacetoacetotrimethylolpropane, benzylacetoacetate, ⁇ -acetyl- ⁇ -butyrolactone, tert-butylacetoacetate and ethylacetoacetate.
  • the 1, 3-dicarbonyl compounds may be used alone or in admixture.
  • the 1,3-dicarbonyl compound is preferably added to the resin mixture in an amount of 1 to 15% by weight, more preferably 6 to 10% by weight.
  • Suitable inhibitors are the inhibitors customarily used for radically polymerizable compounds, as are known to the person skilled in the art, such as phenolic compounds and non-phenolic compounds.
  • Phenolic inhibitors which are often constituents of commercial free-radically curing reaction resins are phenols, such as 2-methoxyphenol, 4-methoxyphenol, 2,6-di-tert-butyl-4-methylphenol, 2,4-di-tert-butylphenol, 2,6-di-tert-butylphenol, 2,4,6-trimethylphenol, 2,4,6-tris (dimethylaminomethyl) phenol, 4,4'-thio-bis (3-methyl-6-tert-butylphenol), 4,4'-isopropylidenediphenol, 6,6'-di-tert-butyl-4,4'-bis (2,6-di-tert-butylphenol), 1, 3,5-trimethyl-2,4,6- tris (3,5-di-tert-butyl-4-hydroxybenzyl) benzene, 2,2'-methylene-di-p-cresol, pyrocatechol and butyl catechols, such as 4-tert-butylpyr
  • the performance of a reaction resin mortar composition in the brick can also be increased by using at least one stable A / Oxyl radical or 4-hydroxy-3,5-di-tert as inhibitor Butyltoluene is used.
  • the resin mixture in small amounts may also contain further, above-mentioned inhibitors, essentially for the storage stability of the radically polymerizable compound and thus also the resin mixture and the reactive resin mortar containing them. These may be introduced either from the preparation of the radically polymerizable compound or the reactive diluents or may be added during the formulation of the resin mixture.
  • the inhibitor is selected from stable A / oxyl radicals or 4-hydroxy-3,5-di-tert-butyltoluene.
  • a / -Oxyl radicals (synonymously also referred to herein as nitroxyl radicals) can be used according to the invention, as described in DE 199 56 509 A1.
  • Suitable stable A / oxyl radicals can be prepared from 1-oxyl-2,2,6,6-tetramethylpiperidine, 1-oxyl-2,2,6,6-tetramethylpiperidin-4-ol (also referred to as TEMPOL).
  • Oxyl-2,2,6,6-tetramethylpiperidin-4-one also referred to as TEMPON
  • 1-oxyl-2,2,6,6-tetramethyl-4-carboxyl-piperidine also referred to as 4-carboxy-TEMPO
  • 1 -Oxyl-2, 2,5,5-tetramethylpyrrolidine 1 -Oxyl-2,2,5,5-tetramethyl-3-carboxylpyrrolidine
  • 3-carboxy-PROXYL aluminum A / nitrosophenylhydroxylamine , Diethylhydroxylamine be selected.
  • nitroxyl radicals are oximes such as acetaldoxime, acetone oxime, methyl ethyl ketoxime, salicyloxime, benzoxime, glyoximes, dimethylglyoxime, acetone-0- (benzyloxycarbonyl) oxime, or indoline nitroxyl radicals such as 2,3-Dihydro-2,2-diphenyl-3- (phenylimino) -1H-indole-1-oxylnitroxide, or beta-phosphorylated nitroxyl radicals, such as 1- (diethoxyphosphinyl) -2,2-dimethylpropyl-1, 1- dimethylmethyl nitroxide, and the like.
  • oximes such as acetaldoxime, acetone oxime, methyl ethyl ketoxime, salicyloxime, benzoxime, glyoximes, dimethylglyoxime, acetone-0- (benzyloxycarbonyl) oxime
  • the polymerization inhibitor is selected from the group consisting of piperidinyl A / oxyl, tetrahydropyrrole A / oxyl, indoline A / oxyl, beta-phosphorylated A / oxyl radicals and 4-hydroxy-3,5-di-tert-butyltoluene.
  • the inhibitor is added to the resin mixture preferably in an amount of 0.005 to 2% by weight, more preferably 0.05 to 1% by weight.
  • a combination of 1, 3-dicarbonyl compound as a reactive diluent and N-oxyl radical or 4-hydroxy-3,5-di-tert-butyltoluol has been found to be an inhibitor.
  • the 1,3-dicarbonyl compound in excess over the inhibitor, the weight ratio of the at least one 1,3-dicarbonyl compound and the polymerization inhibitor being from 30: 1 to 150: 1, preferably 50: 1 to 150 : 1, more preferably 75: 1 to 135: 1.
  • the weight ratio of the at least one 1,3-dicarbonyl compound and the polymerization inhibitor being from 30: 1 to 150: 1, preferably 50: 1 to 150 : 1, more preferably 75: 1 to 135: 1.
  • Suitable free-radically polymerizable compounds according to the invention are ethylenically unsaturated compounds, compounds having carbon-carbon triple bonds and thiol-Yn / En resins, as known to the person skilled in the art.
  • the group of ethylenically unsaturated compounds which are styrene and derivatives thereof, (meth) acrylates, vinyl esters, unsaturated polyesters, vinyl ethers, allyl ethers, itaconates, dicyclopentadiene compounds and unsaturated fats, of which in particular unsaturated polyester resins and vinyl ester resins are suitable and described for example in EP 1 935 860 A1, DE 195 31 649 A1, WO 02/051903 A1 and WO 10/108939 A1.
  • Vinyl ester resins are most preferred because of their hydrolytic resistance and excellent mechanical properties.
  • Suitable unsaturated polyesters which may be used in the resin composition of the present invention are classified into the following categories as described by M. Malik et al. in J.M.S. - Rev. Macromol. Chem. Phys., C40 (2 and 3), p.139-165 (2000):
  • Ortho resins are based on phthalic anhydride, maleic anhydride or fumaric acid, and glycols such as 1,2-propylene glycol, ethylene glycol, diethylene glycol, triethylene glycol, 1,3-propylene glycol, dipropylene glycol, tripropylene glycol, neopentyl glycol or hydrogenated bisphenol-A;
  • Iso resins These are prepared from isophthalic acid, maleic anhydride or fumaric acid and glycols. These resins may contain higher levels of reactive diluents than the ortho resins;
  • bisphenol A fumarates these are based on ethoxylated bisphenol-A and fumaric acid;
  • HET acid resins hexachloro-endo-methylene-tetrahydrophthalic acid resins: resins obtained from chlorine-bromine-containing anhydrides or phenols in the production of unsaturated polyester resins.
  • DCPD resins can be distinguished as unsaturated polyester resins.
  • the class of DCPD resins is obtained either by modification of one of the above resin types by Diels-Alder reaction with cyclopentadiene, or alternatively by a first reaction of a dicarboxylic acid, eg maleic acid, with dicyclopentadienyl, followed by a second reaction, the ordinary production of a unsaturated polyester resin, the latter being referred to as a DCPD maleated resin.
  • the unsaturated polyester resin preferably has a molecular weight Mn in the range of 500 to 10,000 daltons, more preferably in the range of 500 to 5000, and even more preferably in the range of 750 to 4000 (according to ISO 13885-1).
  • the unsaturated polyester resin has an acid value in the range of 0 to 80 mg KOH / g resin, preferably in the range of 5 to 70 mg KOH / g resin (according to ISO 21 14-2000).
  • the acid value is preferably 0 to 50 mg KOH / g resin.
  • vinyl ester resins are oligomers, prepolymers or polymers having at least one (meth) acrylate end group, so-called (meth) acrylate-functionalized resins, including urethane (meth) acrylate resins and epoxy (meth) acrylates.
  • Vinyl ester resins which have unsaturated groups only in the terminal position are obtained, for example, by reaction of epoxide oligomers or polymers (eg bisphenol A digylcidyl ether, epoxides of the phenol novolak type or epoxide oligomers based on tetrabromobisphenol A) with, for example (Meth) acrylic acid or (meth) acrylamide.
  • Preferred vinyl ester resins are (meth) acrylate-functionalized resins and resins obtained by reacting an epoxy oligomer or polymer with methacrylic acid or methacrylamide, preferably with methacrylic acid. Examples of such compounds are known from the publications US 3 297 745 A, US 3 772 404 A, US 4 618 658 A, GB 2 217 722 A1, DE 37 44 390 A1 and DE 41 31 457 A1.
  • Particularly suitable vinyl ester resins are (meth) acrylate-functionalized resins which, for example, by reacting di- and / or higher-functional isocyanates with suitable acrylic compounds, optionally with the participation of hydroxy compounds, which contain at least two hydroxyl groups, as described, for example, in DE 3940309 A1 are obtained.
  • isocyanates it is possible to use aliphatic (cyclic or linear) and / or aromatic di- or higher-functional isocyanates or prepolymers thereof. The use of such compounds serves to increase the wettability and thus the improvement of the adhesion properties. Preference is given to aromatic di- or higher-functional isocyanates or prepolymers thereof, with aromatic di- or higher-functional prepolymers being particularly preferred.
  • tolylene diisocyanate (TDI), diisocyanatodiphenylmethane (MDI) and polymeric diisocyanatodiphenylmethane (pMDl) may be mentioned to increase chain stiffening and hexane diisocyanate (HDI) and isophorone diisocyanate (IPDI) which improve flexibility, of which polymeric diisocyanatodiphenylmethane (pMDl) is most preferred
  • Acrylic acids and acrylic acid substituted on the hydrocarbon radical such as methacrylic acid, hydroxyl-containing esters of acrylic or methacrylic acid with polyhydric alcohols, pentaerythritol tri (meth) acrylate, glycerol di (meth) acrylate, such as trimethylolpropane di (meth) acrylate,
  • Neopentylglycol mono (meth) acrylate suitable. Preference is given to acrylic or methacrylic acid hydroxyalkyl esters, such as hydroxyethyl (meth) acrylate,
  • hydroxy compounds are suitable dihydric or higher alcohols, such as derivatives of ethylene or propylene oxide, such as ethanediol, di- or triethylene glycol, propanediol, dipropylene glycol, other diols, such as 1, 4-butanediol, 1, 6-hexanediol, Neopentylglycol, diethanolamine, further bisphenol A or F or their ethox / propoxylation and / or hydrogenation or halogenation products, higher alcohols such as glycerol, trimethylolpropane, hexanetriol and pentaerythritol, hydroxyl-containing polyethers, for example oligomers of aliphatic or aromatic oxiranes and / or higher cyclic ethers, such as ethylene oxide, propylene oxide, styrene oxide and furan, polyethers containing aromatic structural units in the main chain, such as those of bisphenol A or F
  • hydroxy compounds having aromatic structural units for chain-stiffening the resin hydroxy compounds containing unsaturated structural units, such as fumaric acid, for increasing the crosslinking density
  • hydroxy compounds containing unsaturated structural units such as fumaric acid
  • branched or star-shaped hydroxy compounds in particular trihydric or higher alcohols and / or polyethers or polyesters, and the like
  • Structural units containing, branched or star-shaped urethane (meth) acrylates to achieve lower viscosity of the resins or their solutions in reactive diluents and higher reactivity and crosslinking density.
  • the vinyl ester resin preferably has a molecular weight Mn in the range of 500 to 3000 daltons, more preferably 500 to 1500 daltons (according to ISO 13885-1).
  • the vinyl ester resin has an acid value in the range of 0 to 50 mg KOH / g resin, preferably in the range of 0 to 30 mg KOH / g resin (according to ISO 21 14-2000).
  • the resin may contain other reactive groups that can be polymerized with a free-radical initiator, such as peroxides, for example, reactive groups derived from itaconic acid, citraconic acid and allylic groups, and the like.
  • reaction resin mortar contains in addition to the resin mixture just described inorganic and / or organic additives, such as fillers and / or other additives.
  • the proportion of the resin mixture in the reaction resin mortar is preferably 10 to 70% by weight, more preferably 40 to 60% by weight, based on the reaction resin mortar. Accordingly, the proportion of the additives is preferably 90 to 30 wt .-%, more preferably 60 to 40 wt .-%, based on the reaction resin mortar.
  • Fillers are customary fillers, preferably mineral or mineral-like fillers, such as quartz, glass, sand, quartz sand, quartz flour, porcelain, corundum, ceramics, talc, silicic acid (eg fumed silica), silicates, clay, titanium dioxide, chalk, barite , Feldspar, basalt, aluminum hydroxide, granite or sandstone, polymeric fillers such as thermosets, hydraulically hardenable fillers such as gypsum, quicklime or cement (eg Tonerd- or Portland cement), metals such as aluminum, carbon black, furthermore wood, mineral or organic fibers, or the like, or mixtures of two or more thereof, which may be added as a powder, in a granular form or in the form of shaped articles, use.
  • mineral or mineral-like fillers such as quartz, glass, sand, quartz sand, quartz flour, porcelain, corundum, ceramics, talc, silicic acid (eg fumed silica), silicates,
  • the fillers may be in any form, for example as a powder or flour or as a shaped body, for. In cylindrical, annular, spherical, platelet, stick, saddle or crystal form, or further in fibrous form (fibrillar fillers), and the corresponding base particles preferably have a maximum diameter of 10 mm. Fillers are present in the respective component preferably in an amount of up to 90, in particular 3 to 85, especially 5 to 70 wt .-% present.
  • thixotropic agents such as optionally organically aftertreated fumed silica, bentonites, alkyl and methylcelluloses, castor oil derivatives or the like, plasticizers, such as phthalic or sebacic acid esters, stabilizers, antistatic agents, thickeners, flexibilizers, curing catalysts, rheological aids, wetting agents, coloring additives, such as dyes or in particular pigments, for example for different staining of the components for better control of their mixing, or the like, or mixtures of two or more thereof possible.
  • plasticizers such as phthalic or sebacic acid esters, stabilizers, antistatic agents, thickeners, flexibilizers, curing catalysts, rheological aids, wetting agents
  • coloring additives such as dyes or in particular pigments, for example for different staining of the components for better control of their mixing, or the like, or mixtures of two or more thereof possible.
  • Non-reactive diluents can also be present, preferably in an amount of up to 30% by weight, based on the particular component (reaction resin mortar, hardener), for example from 1 to 20% by weight, such as lower alkyl ketones, e.g. As acetone, di-lower alkyl-lower alkanoylamides, such as dimethylacetamide, lower alkylbenzenes, such as xylenes or toluene, phthalic acid esters or paraffins, or water.
  • a free-radical initiator in particular a peroxide, is used as the curing agent for the free-radically polymerizable compound.
  • the radical initiator it is additionally possible to use an accelerator as an additive.
  • an accelerator as an additive.
  • fast-curing reaction resin mortars are obtained, which are cold-curing.
  • the accelerator is stored separately from the curing agent and may be added to the resin mixture.
  • Suitable accelerators which are usually added to the resin mixture are known to those skilled in the art. If peroxides are used as hardening agents, the accelerator is, for example, an amine, preferably a tertiary amine and / or a metal salt.
  • Suitable amines are selected from the following compounds, which are described, for example, in US 2011071234 A1: dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, n-propylamine, di-n-propylamine, tri-n-propylamine, isopropylamine, diisopropylamine, triisopropylamine, n-butylamine, isobutylamine, tert-butylamine, di-n-butylamine, diisobutylamine, tri-isobutylamine, pentylamine, isopentylamine, diisopentylamine, hexylamine, octylamine, dodecylamine, laurylamine, stearylamine, aminoethanol, diethanolamine, triethanolamine, aminohexanol, ethoxyaminoethane, dimethyl (2-chloroethyl) amine, 2-
  • Preferred amines are aniline derivatives and ⁇ , ⁇ -bisalkylarylamines, such as ⁇ , ⁇ , - dimethylaniline, ⁇ , ⁇ -diethylaniline, N, N-dimethyl-p-toluidine, N, N-bis (hydroxyalkyl) arylamines, N, N Bis (2-hydropoxyethyl) aniline, N, N-bis (2-hydroxyethyl) toluidine, N, N-bis (2-hydroxypropyl) aniline, N, N-bis (2-hydroxypropyl) toluidine, N, N-bis (3-methacryloyl-2-hydroxypropyl) -p-toluidine, N, N-dibutoxyhydroxypropyl-p-toluidine and 4,4'-bis (dimethylamino) diphenylmethane and their ethoxylated and / or propoxylated derivatives.
  • aniline derivatives such as ⁇ , ⁇
  • Polymeric amines such as those obtained by polycondensation of N, N-bis (hydroxylalkyl) aniline with dicarboxylic acids or by polyaddition of ethylene oxide to these amines, are also suitable as accelerators.
  • Suitable metal salts are, for example, cobalt octoate or cobalt naphthenoate and iron, vanadium, potassium, calcium, copper, manganese or zirconium carboxylates.
  • an accelerator it is used in an amount of 0.2 to 3 wt .-%, preferably 0.3 to 2 wt .-%, based on the resin mixture.
  • the resin mixture may additionally contain a coupling agent.
  • an adhesion promoter improves the cross-linking of the borehole wall with the dowel mass, so that the adhesion increases in the hardened state. This is for the use of the two-component dowel material, e.g. in diamond drilled wells and increases the load values.
  • Suitable adhesion promoters are selected from the group of silanes which are functionalized with further reactive organic groups and can be incorporated into the polymer network, and which in particular have hydrolyzable groups. In this regard, reference is made to the publication DE 10 2009 059 210 A1, the content of which is hereby incorporated into the application.
  • the reaction resin mortar according to the invention is particularly suitable as a resin component for a mortar composition which is suitable for construction purposes.
  • the reaction resin mortar is particularly suitable as a resin component for a dowel mass for chemical attachment in mineral substrates.
  • the reaction resin mortar can be completely contained in one component and form this substantially.
  • the reaction resin mortar can be divided into several, generally spatially separated, components.
  • the component containing the curing agent further contains inorganic and / or organic additives (hardeners), wherein the additives may be the same as may be added to the reaction resin mortar, as well as water or other liquid auxiliaries.
  • the aggregates are usually about Fillers and / or additives.
  • the additives are used in amounts of 20 to 90 wt .-%, preferably 50 to 80 wt .-%, based on the curing agent.
  • the hardener is usually completely contained in a component which is desirably other than that containing the reaction resin mortar, so that the curing agent is reaction-inhibitingly separated from the radically polymerizable compound and the other constituents of the reaction resin mortar which can radically polymerize is.
  • the hardener also forms another component of the two-component or multi-component mortar system.
  • the hardener can also be divided into several components.
  • the component containing the reaction resin mortar or the components containing the reaction resin mortar divided by weight or ingredient is referred to as a resin component.
  • the component containing the hardener or the components containing the weight or constituent hardener is referred to as the hardener component.
  • another object of the invention is a two- or multi-component mortar system comprising a reaction resin mortar described above and reaction inhibiting separately a hardener comprising a curing agent and inorganic and / or organic additives.
  • the mortar system is formulated as a two-component mortar system, wherein the one component contains the reaction resin mortar (resin component) and the other component, the curing agent (hardener component).
  • the two components are suitably arranged reaction-inhibiting separately.
  • the curing is initiated with an inorganic or organic peroxide as a curing agent.
  • peroxides known to those skilled in the art used to cure unsaturated polyester resins and vinyl ester resins can be used.
  • Such peroxides include organic and inorganic peroxides, either liquid or solid, with hydrogen peroxide also being used.
  • suitable peroxides are peroxycarbonates (of the formula -OC (O) O-), peroxyesters (of the formula -C (O) OO-), diacyl peroxides (of the formula -C (O) OOC (O) -), dialkyl peroxides (of the formula -00-) and the like. These may be present as oligomer or polymer.
  • a comprehensive set of examples of suitable peroxides is described, for example, in US 2002/0091214 A1, paragraph [0018].
  • the peroxides are preferably selected from the group of organic peroxides.
  • Suitable organic peroxides are: tertiary alkyl hydroperoxides such as tert-butyl hydroperoxide, and other hydroperoxides such as cumene hydroperoxide, peroxyesters or peracids such as tert-butyl peresters, benzoyl peroxide, peracetates and perbenzoates, lauryl peroxide including (di) peroxyesters, perethers such as peroxy diethyl ether, perketones, such as methyl ethyl ketone peroxide.
  • the organic peroxides used as curing agents are often tertiary peresters or tertiary hydroperoxides, i. Peroxide compounds having tertiary carbon atoms bonded directly to an -O-O-acyl or -OOH group. But mixtures of these peroxides with other peroxides can be used according to the invention.
  • the peroxides may also be mixed peroxides, i. Peroxides which have two different peroxide-carrying units in one molecule.
  • benzoyl peroxide (BPO) is preferably used for curing.
  • the hardener component in an amount of 0.1 to 3 wt .-%, and preferably from 0.25 to 2 wt .-%, based on the total weight of the two- or Multi-component mortar system, ie the reaction resin mortar and the hardener.
  • the reaction resin mortar may contain the accelerator in an amount of from 0.1 to 1.5% by weight, and preferably from 0.25 to 1.0% by weight, based on the total weight of the two - or multi-component mortar system.
  • the reaction resin mortar also suitably contains the inhibitor.
  • the reaction resin mortar may contain the inhibitor in an amount of 0.003 to 0.35 wt%, and preferably 0.01 to 0.2 wt%, based on the total weight of the two- or three-component mortar multi-component mortar system.
  • the optionally added in the resin masterbatch or to stabilize the resin mixture further inhibitors must be included in the calculation of the amount, so that the total amount of inhibitor is in the specified range.
  • Conventional mortar compositions based on the total weight of reaction resin mortar and hardener 1, 5 to 3 wt .-% curing agent, preferably a peroxide, and more preferably dibenzoyl peroxide (BPO).
  • the hardener Depending on the mixing ratio, the hardener must contain 7 to 15% of the peroxide. This leads to the characterization of the hardener as "sensitizing." No curing agents with a BPO content of less than 1% are labeled.
  • the concentrations of accelerator and inhibitor must be significantly reduced. These are for the accelerator in the range of 0, 1 to 0.5 wt .-% and for the inhibitor in the range of 0.003 to 0.07 wt .-%.
  • a preferred embodiment of the invention relates to a two- or multi-component mortar system, wherein the accelerator in an amount of 0, 1 to 0, respectively, refers to the total weight of the two-component or multi-component mortar system , 5 wt .-%, the inhibitor in an amount of 0.003 to 0.07 wt .-% and the curing agent in an amount of 0.1 to 0.35 wt .-%, in each case based on the total weight of the two - or multi-component mortar system.
  • the two- or multi-component mortar composition according to the invention not only to avoid the identification of the peroxide content, but also to provide a mortar composition which at a wide mixing ratio of reaction resin mortar to hardener in the range of 3: 1 to 5: 1 by weight. Share with a sufficient processing time to achieve good curing and high load values.
  • the resin component in addition to the reaction resin mortar additionally contains a hydraulically setting or polycondensable inorganic compound and the hardener component in addition to the curing agent or water.
  • a hydraulically setting or polycondensable inorganic compound for example Portland cement or aluminate cement, particular preference being given to iron oxide-free or low-iron cements.
  • a hydraulically setting inorganic compound and gypsum can be used as such or in admixture with the cement.
  • the resin component contains from 8 to 25% by weight of radically polymerizable resin, from 8 to 25% by weight of reactive diluent, from 0.1 to 0.5% by weight of accelerator and from 0.003 to 0.07 wt .-% Inhibitor, 40 to 70 wt .-% filler and 0.5 to 5 wt .-% thickener and the hardener component 0.1 to 0.35 wt .-% peroxide, 3 to 15 wt .-% water, 5 to 25 wt .- Fillers and 0.1 to 3 wt .-% thickener, each based on the total weight of the two-component mortar system.
  • the invention further provides the use of the two- or multi-component mortar system for construction purposes.
  • the term "for building” includes the construction bonding of concrete / concrete, steel / concrete or steel / steel or one of the materials mentioned on other mineral materials, the structural reinforcement of components made of concrete, masonry and other mineral materials, the reinforcement applications with fiber reinforced polymers of construction objects, the chemical attachment to surfaces of concrete, steel or other mineral materials, in particular the chemical attachment of construction elements and anchoring means, such as anchor rods, anchor bolts, (threaded) rods, (threaded) sleeves, concrete iron, screws and like, in boreholes in various substrates, such as (steel) concrete, masonry, other mineral materials, metals (eg steel), ceramics, plastics, glass and wood.
  • the two-component or multi-component mortar system according to the invention is particularly suitable for the chemical attachment of construction elements and anchoring agents in mineral substrates such as concrete, masonry (solid brick or solid brickwork), hollow masonry (hollow brick or perforated brick masonry), lightweight or aerated concrete, in particular concrete and bricks.
  • mineral substrates such as concrete, masonry (solid brick or solid brickwork), hollow masonry (hollow brick or perforated brick masonry), lightweight or aerated concrete, in particular concrete and bricks.
  • Examples 1 to 29 and Comparative Examples V1 to V8 Resin blends having the compositions shown in Tables 1 to 6 were prepared by homogeneously mixing the ingredients together. The quantities are in each case parts by weight (parts by weight).
  • the hardener component used was a mixture of 1 part by weight of dibenzoyl peroxide, 28 parts by weight of water, 4 parts by weight of pyrogenic silica, 63 parts by weight of quartz (0-80 ⁇ m) and 4 parts by weight of alumina.
  • the resin component and the hardener component were mixed with each other in a weight ratio of 3: 1, and the resulting masses were used to determine the gelation times and the failure loads in the masonry brick.
  • the determination of the gelation times of the mortar compositions obtained in this manner is carried out with a commercially available device (GELNORM® gel timer) at a temperature of 25 ° C.
  • GELNORM® gel timer a commercially available device
  • the components are mixed and tempered immediately after mixing in the silicone bath to 25 ° C and measured the temperature of the sample.
  • the sample itself is located in a test tube, which is placed in a submerged in silicone bath air jacket for temperature control.
  • the temperature of the sample is plotted against time.
  • the evaluation is carried out according to DIN16945, sheet 1 and DIN 16916.
  • the pot life is the time at which a temperature increase of 10K is reached, here from 25 ° C to 35 ° C.
  • the results of the gel time determinations are listed in Tables 1 to 6 below.
  • the failure loads (kN) determined in this case are listed as mean values in Tables 1 to 6 below.
  • the viscosity of the resin mixtures was determined according to DIN EN ISO 2884 with a rheometer RS 600 from Haake, Düsseldorf, a measuring geometry plate cone 0 60 mm, 1 ° titanium (C60 / 1 ° Ti), gap 0.052 mm at a temperature of 23 ° C and a shear rate of 150 s " measured.
  • Table 1 Composition of resin blends, gel times and failure loads
  • compositions according to the invention give significantly better failure loads than with the compositions prepared according to the comparative examples.

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Abstract

L'invention concerne un mortier de résines de réaction comprenant un mélange de résines contenant au moins un composé polymérisable par voie radicalaire, au moins un diluant réactif et au moins un inhibiteur, la viscosité du mélange de résines étant ajustée à une valeur déterminée. L'invention concerne également un système de mortier à deux composants ou davantage ainsi que l'utilisation du mortier de résines de réaction et du système de mortier à deux composants ou davantage à des fins de construction, en particulier pour des scellements chimiques dans des fonds minéraux.
EP14741911.3A 2013-07-24 2014-07-23 Mortiers de résines de réaction, système de mortier à plusieurs composants et leur utilisation Withdrawn EP3024797A1 (fr)

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EP13177785.6A EP2829525A1 (fr) 2013-07-24 2013-07-24 Mortier à résine réactive, système de mortier multicomposants et leur utilisation
EP14741911.3A EP3024797A1 (fr) 2013-07-24 2014-07-23 Mortiers de résines de réaction, système de mortier à plusieurs composants et leur utilisation
PCT/EP2014/065803 WO2015011183A1 (fr) 2013-07-24 2014-07-23 Mortiers de résines de réaction, système de mortier à plusieurs composants et leur utilisation

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EP3424971A1 (fr) * 2017-07-03 2019-01-09 HILTI Aktiengesellschaft Composés de méthacrylate d'uréthane comprenant une résine de réaction, composants de résine de réaction et système de résine de réaction et son utilisation
US12098266B2 (en) * 2018-11-29 2024-09-24 Dow Global Technologies Llc Thermoplastic polyolefin compositions useful for odor reduction
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CA2918945A1 (fr) 2015-01-29
RU2016105800A (ru) 2017-08-29
WO2015011183A1 (fr) 2015-01-29
US20160137552A1 (en) 2016-05-19

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