CH684795A5 - Monomer formulations for the construction industry. - Google Patents
Monomer formulations for the construction industry. Download PDFInfo
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- CH684795A5 CH684795A5 CH1845/92A CH184592A CH684795A5 CH 684795 A5 CH684795 A5 CH 684795A5 CH 1845/92 A CH1845/92 A CH 1845/92A CH 184592 A CH184592 A CH 184592A CH 684795 A5 CH684795 A5 CH 684795A5
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- Switzerland
- Prior art keywords
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- 239000000178 monomer Substances 0.000 title claims description 24
- 239000000203 mixture Substances 0.000 title description 7
- 238000010276 construction Methods 0.000 title description 2
- 238000009472 formulation Methods 0.000 title 1
- 238000002360 preparation method Methods 0.000 claims description 28
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 11
- 239000004071 soot Substances 0.000 claims description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- -1 alicyclic dicarboxylic acid ester Chemical class 0.000 claims description 5
- 239000004567 concrete Substances 0.000 claims description 5
- 239000000945 filler Substances 0.000 claims description 5
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 5
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000006229 carbon black Substances 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 239000011159 matrix material Substances 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 229920000570 polyether Polymers 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 239000000853 adhesive Substances 0.000 claims description 3
- 230000001070 adhesive effect Effects 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000005266 casting Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 1
- 229920003232 aliphatic polyester Polymers 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000002986 polymer concrete Substances 0.000 description 8
- 101000623895 Bos taurus Mucin-15 Proteins 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 239000004576 sand Substances 0.000 description 6
- 229910052723 transition metal Inorganic materials 0.000 description 5
- 239000004342 Benzoyl peroxide Substances 0.000 description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
- 239000006004 Quartz sand Substances 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000005452 bending Methods 0.000 description 3
- 150000002432 hydroperoxides Chemical class 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 150000002696 manganese Chemical class 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- HQOVXPHOJANJBR-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound CC(C)(C)OOC(C)(CC)OOC(C)(C)C HQOVXPHOJANJBR-UHFFFAOYSA-N 0.000 description 1
- MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 description 1
- ODGCZQFTJDEYNI-UHFFFAOYSA-N 2-methylcyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1(C)C=CCCC1C(O)=O ODGCZQFTJDEYNI-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical group CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229920005822 acrylic binder Polymers 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- UPIWXMRIPODGLE-UHFFFAOYSA-N butyl benzenecarboperoxoate Chemical compound CCCCOOC(=O)C1=CC=CC=C1 UPIWXMRIPODGLE-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- FJDJVBXSSLDNJB-LNTINUHCSA-N cobalt;(z)-4-hydroxypent-3-en-2-one Chemical compound [Co].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FJDJVBXSSLDNJB-LNTINUHCSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- SPTHWAJJMLCAQF-UHFFFAOYSA-M ctk4f8481 Chemical compound [O-]O.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-M 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000005608 naphthenic acid group Chemical group 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910021487 silica fume Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
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
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/009—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone characterised by the material treated
-
- 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
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
- C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
- C04B41/48—Macromolecular compounds
- C04B41/483—Polyacrylates
-
- 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
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/60—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone of only artificial stone
- C04B41/61—Coating or impregnation
- C04B41/62—Coating or impregnation with organic materials
- C04B41/63—Macromolecular compounds
-
- 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
- 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
- C04B2111/60—Flooring materials
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Ceramic Engineering (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Paints Or Removers (AREA)
- Polymerisation Methods In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
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CH 684 795 A5 CH 684 795 A5
Beschreibung description
Die Erfindung betrifft Monomerzubereitungen, die in verschiedenen Bereichen der Bauindustrie eingesetzt werden können, und insbesondere den Zusatz von Russ und/oder von polyfunktionellen Oligome-ren zur Verbesserung der Eigenschaften der damit hergestellten Polymermatrix-Kombinationen. Die schnellhärtenden Zubereitungen mit Füllstoffen dienen zur Herstellung von Belägen, Beschichtungen, Gussmassen, zur Reparatur von Betongegenständen und als Klebestoff, ohne Füllstoff können sie für die gleichen Zwecke injiziert werden. The invention relates to monomer preparations which can be used in various areas of the construction industry, and in particular the addition of carbon black and / or polyfunctional oligomers to improve the properties of the polymer matrix combinations produced therewith. The quick-hardening preparations with fillers are used for the production of coverings, coatings, casting compounds, for the repair of concrete objects and as an adhesive. Without fillers, they can be injected for the same purposes.
Polymerbetonmassen, die durch schnelle Aushärtung von Acrylmonomeren in Gegenwart von verschiedenen Zusätzen und Füllstoffen, insbesondere Sand hergestellt werden, sind als Bodenbeläge und Beschichtungen von Betongegenständen bekannt und zeichnen sich durch hohe mechanische Belastbarkeit aus. Polymer concrete masses, which are produced by the rapid hardening of acrylic monomers in the presence of various additives and fillers, especially sand, are known as floor coverings and coatings of concrete objects and are characterized by high mechanical strength.
Es wurde nun gefunden, dass die Eigenschaften der erhaltenen Polymerbetonmassen noch wesentlich verbessert werden können, wenn die zum Einsatz gelangenden Monomerzubereitungen bestimmte polyfunktionelle Oligomere enthalten und/oder Russ zugesetzt wird. It has now been found that the properties of the polymer concrete compositions obtained can be significantly improved if the monomer preparations used contain certain polyfunctional oligomers and / or soot is added.
Gegenstand der Erfindung sind also Monomerzubereitungen auf Basis von Acrylmonomeren mit einem Flammpunkt über 50°C, die 0,01 bis 7 Gewichtsprozent Russ und/oder polyfunktionelie Oligomere auf Basis von Polyester oder Poiyäther/Urethan/Acrylat enthalten, sowie durch Aushärtung dieser Zubereitungen erhaltene Polymermatrix-Kombinationen mit und ohne Füllstoffen. The invention thus relates to monomer preparations based on acrylic monomers with a flash point above 50 ° C., which contain 0.01 to 7 percent by weight carbon black and / or polyfunctional oligomers based on polyester or polyether / urethane / acrylate, and also polymer matrix obtained by curing these preparations Combinations with and without fillers.
Die Mengenangaben für den Russ-Zusatz beziehen sich auf die Menge des Acryibindemitteis und betragen bevorzugt 0,1 bis 3, am meisten bevorzugt 0,1 bis 0,5 Gewichtsprozent Russ mit einer BET-Fläche von 20—460 m2/g. Es können verschiedene Russarten, z.B. Gasruss, Flammruss und Furnace-Russ verwendet werden. The amounts for the soot additive relate to the amount of acrylic binder and are preferably 0.1 to 3, most preferably 0.1 to 0.5 percent by weight of soot with a BET area of 20-460 m 2 / g. Different types of soot, e.g. Gasruss, Flammruss and Furnace-Russ can be used.
Die erfindungsgemäss enthaltenen Oligomere sind aliphatische oder aromatische, bifunktionelie oder polyfunktionelle Polyester bzw. Polyäther/Urethan-Acrylate mit einem Molekulargewicht von 500-2000, bevorzugt 1000-2000 und einer Viskosität von 2000-100 000 mPa s (bei 25°C), bevorzugt von 12 000 bis 100 000, am meisten bevorzugt von 60-75 000 mPa s. Sie werden durch Einpolymerisierung von Acrylsäure- bzw. Methacrylsäurerestern in Polyester bzw. Polyäther/Urethanen hergestellt und weisen zumindest zwei ungesättigte Bindungen auf, die zur Vernetzung der üblichen Acrylat-Bindemittel dienen. The oligomers contained according to the invention are aliphatic or aromatic, bifunctional or polyfunctional polyesters or polyether / urethane acrylates with a molecular weight of 500-2000, preferably 1000-2000 and a viscosity of 2000-100000 mPa s (at 25 ° C.), preferred from 12,000 to 100,000, most preferably from 60-75,000 mPas. They are produced by polymerizing acrylic acid or methacrylic acid esters into polyester or polyether / urethanes and have at least two unsaturated bonds which are used to crosslink the customary acrylate binders.
Ein geeignetes Produkt ist das von der Firma Rahn, Zürich vertriebene GENOMER T 1200 (alipha-tisch/Triacrylat) mit einem MW = 1000-1200 und einer Viskosität von 70 000 mPa s. Weitere mögliche Produkte sind: A suitable product is the GENOMER T 1200 (aliphatic / triacrylate) sold by Rahn, Zurich, with a MW = 1000-1200 and a viscosity of 70,000 mPa s. Other possible products are:
Name Surname
Firma company
Struktur structure
MW MW
Viskosität viscosity
GENOMER T 1600 GENOMER T 1600
Rahn AG Zürich aliphatisch Triacrylat Rahn AG Zurich aliphatic triacrylate
-1600 -1600
52 000 52,000
GENOMER D 1500 B GENOMER D 1500 B
Rahn AG Zürich aliphatisch Diacrylat Rahn AG Zurich aliphatic diacrylate
EBECRYL 205 EBECRYL 205
UCB Belgien aromatisch Triacrylat UCB Belgium aromatic triacrylate
2000 2000
30 000 30,000
EBECRYL 210 EBECRYL 210
UCB Belgien aromatisch Diacrylat UCB Belgium aromatic diacrylate
1500 1500
4000 4000
EBECRYL 1259 EBECRYL 1259
UCB Belgien aliphatisch Triacrylat UCB Belgium aliphatic triacrylate
2000 2000
14 000 14,000
EBECRYL 1290 EBECRYL 1290
UCB Belgien aliphatisch Hexacrylat UCB Belgium aliphatic hexacrylate
1000 1000
2000 2000
Als Bindemittel dienen die bekannten Acrylatharze, die als Monomere in geeigneten Zubereitungen mit Katalysatoren vermischt werden und dann innerhalb weniger Stunden aushärten zu Polymerbetonmassen. Solche Acrylmonomere sind bestimmte Ester der Acrylsäure oder vorzugsweise Methacrylsäu-re wie sie z.B. in der EP 47 120, USP 4 460 625, 4 097 677, 4 299 761, 4 400 413 und GB 2 220 204 beschrieben worden sind. Auf den Inhalt dieser Patentschriften wird zur Definition dieser Komponente Bezug genommen. Solche Monomere entsprechen der allgemeinen Formel I The known acrylate resins serve as binders, which are mixed as monomers in suitable preparations with catalysts and then harden within a few hours to give polymer concrete compositions. Such acrylic monomers are certain esters of acrylic acid or preferably methacrylic acid as e.g. in EP 47 120, USP 4,460,625, 4,097,677, 4,299,761, 4,400,413 and GB 2,220,204. Reference is made to the content of these patents for the definition of this component. Such monomers correspond to the general formula I.
CH2 = Ç - C -(ORi)„ - 0R2 I CH2 = Ç - C - (ORi) „- 0R2 I
R 0 R 0
worin wherein
R Wasserstoff oder Methyl, R is hydrogen or methyl,
Ri eine Alkylengruppe mit 2 bis 6 C-Atomen, Ri is an alkylene group with 2 to 6 carbon atoms,
n eine ganze Zahl von 1 bis 3 oder Null und n is an integer from 1 to 3 or zero and
R2 einen Rest eines aromatischen oder alicyclischen Dicarbonsäureesters oder, wenn n = 0, einen Dicyclopentenylrest bedeuten. Solche Acrylmonomere haben einen Flammpunkt von mindestens 50°C und bevorzugt über 100°C. R2 is a radical of an aromatic or alicyclic dicarboxylic acid ester or, if n = 0, a dicyclopentenyl radical. Such acrylic monomers have a flash point of at least 50 ° C and preferably above 100 ° C.
Bevorzugt sind solche Ester, in denen R Methyl, Ri eine verzweigte Alkylengruppe mit 3 oder 4 C- Preferred esters are those in which R is methyl, Ri is a branched alkylene group with 3 or 4 carbon atoms.
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65 65
CH 684 795 A5 CH 684 795 A5
Atomen, n die Zahl 1 und R2 den Rest einer Tetrahydrophthalsäure, die ausserdem mit einem einfachen Alkohol wie Methanol oder Äthanol verestert ist, bedeuten. Atoms, n is 1 and R2 is the residue of a tetrahydrophthalic acid, which is also esterified with a simple alcohol such as methanol or ethanol.
Diese Acrylester gemäss der Formel I können auch, wie üblich, mit einfachen Estern der Acryl- bzw. Methacrylsäure gemischt werden zur Erzielung von bestimmten Eigenschaften der erhaltenen Polymerbetonmassen. Ein Beispiel solcher Zusätze ist das Hydroxypropylmethacrylat. Die Anteile der Monomere sind dabei wie folgt: die Acrylate der Formel I (Komponente I) von 20 bis 100 Gewichtsprozent, bevorzugt 50-95 Gewichtsprozent und die einfachen Acrylate (Komponente II) von 0 bis 80 Gewichtsprozent, bevorzugt 5-50 Gewichtsprozent, wenn kein Oligomer enthalten ist. Im Falle von drei Komponenten sind die Anteile: Komponente I 20 bis 93, bevorzugt 50 bis 80 Gewichtsprozent, Komponente II 0 bis 73, bevorzugt 7-37 Gewichtsprozent und das Oligomer von 7 bis 60 Gewichtsprozent, bevorzugt 13-40 Gewichtsprozent. These acrylic esters according to formula I can, as usual, also be mixed with simple esters of acrylic or methacrylic acid in order to achieve certain properties of the polymer concrete compositions obtained. An example of such additives is hydroxypropyl methacrylate. The proportions of the monomers are as follows: the acrylates of the formula I (component I) from 20 to 100 percent by weight, preferably 50-95 percent by weight and the simple acrylates (component II) from 0 to 80 percent by weight, preferably 5-50 percent by weight, if no oligomer is included. In the case of three components, the proportions are: component I 20 to 93, preferably 50 to 80 percent by weight, component II 0 to 73, preferably 7-37 percent by weight and the oligomer from 7 to 60 percent by weight, preferably 13-40 percent by weight.
Als Katalysatoren für die Vernetzung bzw. Aushärtung der erfindungsgemässen Zubereitungen werden organische Peroxide oder Hydroperoxide von Kohlenwasserstoffen mit 3-18 C, die in den Monomeren löslich sind, zusammen mit Salzen oder Komplexen von Übergangsmetallen und/oder aromatischen Aminen als Polymerisationsbeschleunigern eingesetzt. Die Peroxide bzw. Hydroperoxide sind in Mengen von 0,1 bis 5 Gewichtsprozent, die Salze oder Komplexe von Übergangsmetallen in Mengen von 0,0005 bis 2 Gewichtsprozent und die aromatischen Amine in Mengen von 0,1 bis 5 Gewichtsprozent enthalten. Alle Prozentangaben beziehen sich auf das Gesamtgewicht der Monomeren I und II. Beispiele geeigneter Peroxide sind Benzoylperoxid, tert. Butylperbenzoat, Dilaurylperoxid und 2,2-Bis-(tert-butylperoxy)-butan. Geeignete Hydroperoxide sind tert.-Butylhydroperoxid, Cumolhydroperoxid und Diisopropylbenzolhydroperoxid. Organic peroxides or hydroperoxides of hydrocarbons with 3-18 C, which are soluble in the monomers, together with salts or complexes of transition metals and / or aromatic amines as polymerization accelerators are used as catalysts for the crosslinking or curing of the preparations according to the invention. The peroxides or hydroperoxides are present in amounts of 0.1 to 5 percent by weight, the salts or complexes of transition metals in amounts of 0.0005 to 2 percent by weight and the aromatic amines in amounts of 0.1 to 5 percent by weight. All percentages relate to the total weight of the monomers I and II. Examples of suitable peroxides are benzoyl peroxide, tert. Butyl perbenzoate, dilauryl peroxide and 2,2-bis (tert-butylperoxy) butane. Suitable hydroperoxides are tert-butyl hydroperoxide, cumene hydroperoxide and diisopropylbenzene hydroperoxide.
Die Salze oder Komplexe von Übergangsmetallen sind solche, die die oxydative Aushärtung von trocknenden Ölen katalysieren und als Sikkative bekannt sind. Normalerweise handelt es sich um Calcium, Kupfer, Zink, Magnesium, Mangan, Blei, Kobalt, Eisen, Vanadium oder Zirkonium-Salze von höheren aliphatischen (8-30 C) Carbonsäuren oder Naphthensäuren. Bevorzugt sind Kobalt- -und Mangansalze wie Kobaltoctoat, Kobaltnaphthenat, Kobaltacetylacetonat und die entsprechenden Mangansalze. The salts or complexes of transition metals are those that catalyze the oxidative curing of drying oils and are known as siccatives. Usually it is calcium, copper, zinc, magnesium, manganese, lead, cobalt, iron, vanadium or zirconium salts of higher aliphatic (8-30 C) carboxylic acids or naphthenic acids. Cobalt and manganese salts such as cobalt octoate, cobalt naphthenate, cobalt acetylacetonate and the corresponding manganese salts are preferred.
Die gegebenenfalls als Polymerisationsbeschleuniger eingesetzten aromatischen Amine sind für diesen Zweck bekannt. Beispiele sind Anilin, N,N-Dimethyl- oder N,N-Diäthylanilin, entsprechende Toluidi-ne und p-Dimethylaminobenzaldehyd, welche in Mengen von 0,1 bis 6 Gewichtsprozent, bevorzugt 0,1 bis 2 Gewichtsprozent, bezogen auf das Gewicht der Monomerkomponenten, enthalten sind. The aromatic amines optionally used as polymerization accelerators are known for this purpose. Examples are aniline, N, N-dimethyl- or N, N-diethylaniline, corresponding toluidines and p-dimethylaminobenzaldehyde, which in amounts of 0.1 to 6 percent by weight, preferably 0.1 to 2 percent by weight, based on the weight of the Monomer components are included.
Bevorzugt besteht ein solches Katalysatorsystem aus einem Peroxid oder Hydroperoxid, einem aromatischen Amin und einem Übergangsmetallsalz. Such a catalyst system preferably consists of a peroxide or hydroperoxide, an aromatic amine and a transition metal salt.
Ausserdem enthalten die erfindungsgemässen Zubereitungen normalerweise ein im wesentlichen wasserfreies Zuschlagsmaterial (Aggregat), wobei die gesamte Zubereitung 40-95% enthält in Gewichtsprozent. Als Aggregat kommt irgendeine anorganische Verbindung in Betracht, die gegenüber Säuren, Basen und Salzen inert ist. So werden beispielsweise Sand, Kies oder gröbere Zuschlagsstoffe als Voll- oder als Hohlkörper bzw. deren Kombinationen eingesetzt, wie sie für Polymerbetonmassen üblich sind. Für Überzüge werden Feinaggregate wie Feinsand, evtl. gemischt mit Silica fume eingesetzt. Dabei können diese verschiedenen Bestandteile kurz vor der Applikation der Polymerbetonmassen zugegeben werden oder in verschiedenen lagerbeständigen Packungen mit den Monomeren und/ oder Aggregat enthalten sein. So werden beispielsweise das Aggregat, die verschiedenen Monomeren mit dem gegebenenfalls vorhandenen Polymerisationsbeschleuniger und der Polymerisationskatalysator mit dem Ubergangsmetallsalz in getrennten Packungen abgegeben, die kurz vor der Anwendung miteinander vermischt werden. Je nach eingesetztem Katalysator kann auch das Katalysatorsystem (ohne Beschleuniger) mit dem Aggregat oder die Monomermischung mit dem Aggregat vorgemischt werden. In addition, the preparations according to the invention normally contain an essentially water-free aggregate (aggregate), the entire preparation containing 40-95% in weight percent. Any inorganic compound which is inert to acids, bases and salts can be considered as an aggregate. For example, sand, gravel or coarse aggregates are used as solid or hollow bodies or combinations thereof, as are common for polymer concrete masses. Fine aggregates such as fine sand, possibly mixed with silica fume, are used for coatings. These various constituents can be added shortly before the application of the polymer concrete compositions or can be contained in various storage-stable packages with the monomers and / or aggregate. For example, the aggregate, the various monomers with the polymerization accelerator which may be present and the polymerization catalyst with the transition metal salt are dispensed in separate packs which are mixed together shortly before use. Depending on the catalyst used, the catalyst system (without accelerator) can also be premixed with the unit or the monomer mixture with the unit.
Diese Zubereitungen können zur Reparatur von Betongegenständen oder -flächen verwendet werden. Dazu bringt man eine erfindungsgemässe Zubereitung auf die reparaturbedürftige Oberfläche und lässt sie bei der Aussentemperatur aushärten. Sie können aber auch für die Imprägnierung oder Beschich-tung von porösen Materialien, insbesondere von Beton, oder für das Füllen von Rissen verwendet werden. Insbesondere werden aus diesen Zubereitungen sehr widerstandsfähige Bodenbeläge hergestellt. These preparations can be used to repair concrete objects or surfaces. For this purpose, a preparation according to the invention is brought onto the surface in need of repair and is allowed to harden at the outside temperature. But they can also be used to impregnate or coat porous materials, especially concrete, or to fill cracks. In particular, very resistant floor coverings are produced from these preparations.
Neben einer guten Wasserbeständigkeit und Wärmefestigkeit zeichnen sich die erhaltenen Polymerbetonmassen vor allem durch eine erhöhte Schlagzähigkeit, Druck- und Biegezugfestigkeit sowie durch eine erstaunliche Haftzugfestigkeit aus. Die Monomerzubereitungen haben eine verbesserte Reaktivität. In addition to good water resistance and heat resistance, the polymer concrete compositions obtained are characterized above all by increased impact strength, compressive and bending tensile strength and by an astonishing adhesive tensile strength. The monomer preparations have an improved reactivity.
In den folgenden Beispielen bedeuten die Teile Gewichtsteile und die Prozente Gewichtsprozente. Die Temperaturen sind in Celsiusgraden angegeben. In the following examples, parts are parts by weight and percentages are percentages by weight. The temperatures are given in degrees Celsius.
Die Komponente I ist ein Ester des Tetrahydrophthalsäuremonomethylesters und Hydroxypropylmethacrylat. Die Komponente II ist ein Hydroxypropylmethacrylat. Das Oligomer ist das Produkt GENOMER T 1200 der Firma Rahn, Zürich. Component I is an ester of methyl tetrahydrophthalic acid and hydroxypropyl methacrylate. Component II is a hydroxypropyl methacrylate. The oligomer is the GENOMER T 1200 product from Rahn, Zurich.
Der eingesetzte Russ ist ein Furnace-Russ mit BET-Fläche von 80 m2/g (Printex 300 der Firma DEGUSSA). The soot used is a furnace soot with a BET surface area of 80 m2 / g (Printex 300 from DEGUSSA).
Die Topfzeit und die Klebefreiheit der erhaltenen Polymerbetonmasse wird bei Raumtemperatur bestimmt. Die Schlagzähigkeit wird in m Joule/cm2, die Druck- und Biegezugfestigkeit in Newton/mm2 ausgedruckt. Die Prüfungen erfolgen gemäss Standard-Methoden. The pot life and the stickiness of the polymer concrete mass obtained is determined at room temperature. The impact strength is expressed in m Joule / cm2, the compressive and bending tensile strength in Newton / mm2. The tests are carried out according to standard methods.
3 3rd
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
CH 684 795 A5 CH 684 795 A5
Tabelle 1 Table 1
Zubereitung Bsp. 1 Bsp. 2 Bsp. 3 Bsp. 4 Bsp. 5 Bsp. 6 Bsp. 7 Preparation Ex. 1 Ex. 2 Ex. 3 Ex. 4 Ex. 5 Ex. 6 Ex. 7
(zum Vergleich) (for comparison)
Komponente I Component I
10 10th
10 10th
10 10th
10 10th
15 15
15 15
15 15
Komponente II Component II
5 5
5 5
5 5
5 5
- -
- -
- -
Russ Soot
- -
0,02 0.02
0,1 0.1
1 1
0,02 0.02
0,1 0.1
1 1
Cobaltnaphthenat Cobalt naphthenate
0,15 0.15
0,15 0.15
0,15 0.15
0,15 0.15
0,15 0.15
0,15 0.15
0,15 0.15
Benzoylperoxid Benzoyl peroxide
0,8 0.8
0,8 0.8
0,8 0.8
0,8 0.8
0,8 0.8
0,8 0.8
0,8 0.8
Normsand (0-1 mm) Standard sand (0-1 mm)
ca. 54 approx. 54
ca. 54 approx. 54
ca. 54 approx. 54
ca. 54 approx. 54
ca. 54 approx. 54
ca. 54 approx. 54
ca. 54 approx. 54
Quarzsand (0,1-0,3 mm) Quartz sand (0.1-0.3 mm)
ca. 26 approx. 26
ca. 26 approx. 26
ca. 26 approx. 26
ca. 26 approx. 26
ca. 26 approx. 26
ca. 26 approx. 26
ca. 26 approx. 26
Quarzsand (0,04-0,1 mm) Quartz sand (0.04-0.1 mm)
5 5
5 5
5 5
5 5
5 5
5 5
5 5
Topfzeit Pot life
> 1 Tag > 1 day
50 min 50 min
10-15 min 10-15 min
10 min 10 min
50 min 50 min
5-10 5-10
5-8 5-8
Klebefreiheit Stickiness
> 36 Std. > 36 hours
12-24 Std. 10 Std. 12-24 hours 10 hours
5 Std. 5 hours
12-24 Std. 10 Std. 12-24 hours 10 hours
5-10 Std. 5-10 hours
Tabelle 2 Table 2
Zubereitung preparation
Bsp. 1 Bsp. 2 (zum Vergleich) Ex. 1 Ex. 2 (for comparison)
Bsp. 3 Ex. 3
Bsp. 4 Ex. 4
Bsp. 5 Ex. 5
Bsp. 6 Ex. 6
Bsp. 7 Ex. 7
Komponente I Component I
15 15
13 13
11 11
6 6
8 8th
6 6
4 4th
Komponente II Component II
- -
- -
- -
- -
4 4th
3 3rd
2 2nd
Oligomer Oligomer
- -
2 2nd
4 4th
9 9
3 3rd
6 6
9 9
Cobaltnaphthenat Cobalt naphthenate
0,15 0.15
0,15 0.15
0,15 0.15
0,15 0.15
0,15 0.15
0,15 0.15
0,15 0.15
Benzoylperoxid Benzoyl peroxide
0,8 0.8
0,8 0.8
0,8 0.8
0,8 0.8
0,8 0.8
0,8 0.8
0,8 0.8
Normsand (0-1 mm) Standard sand (0-1 mm)
ca. 54 approx. 54
ca. 54 approx. 54
ca. 54 approx. 54
ca. 54 approx. 54
ca. 54 approx. 54
ca. 54 approx. 54
ca. 54 approx. 54
Quarzsand (0,1-0,3 mm) Quartz sand (0.1-0.3 mm)
ca. 26 approx. 26
ca. 26 approx. 26
ca. 26 approx. 26
ca. 26 approx. 26
ca. 26 approx. 26
ca. 26 approx. 26
ca. 26 approx. 26
Quarzsand (0,04-0,1 mm) Quartz sand (0.04-0.1 mm)
5 5
5 5
5 5
5 5
5 5
5 5
5 5
Schlagzähigkeit Impact strength
80 80
190 190
193 193
250 250
170 170
200 200
240 240
Biegezugfestigkeit Bending tensile strength
17 17th
27 27
29 29
27 27
31 31
34 34
32 32
Druckfestigkeit Compressive strength
46 46
54 54
58 58
68 68
70 70
71 71
70 70
4 4th
O) O)
en en
œ o on o en œ o on o en
45». o co en co o 45 ». o co en co o
N) en N) en
Tabelle 3 Table 3
Zubereitung preparation
Bsp. 1 Ex. 1
Bsp. 2 Ex. 2
Bsp. 3 Ex. 3
Bsp. 4 Ex. 4
Bsp. 5 Ex. 5
Bsp. 6 Ex. 6
Bsp. 7 Ex. 7
Bsp. 8 Ex. 8
Bsp. 9 Ex. 9
Bsp. 10 Ex. 10
Komponente 1 Component 1
7,3 7.3
7,3 7.3
7,3 7.3
7,3 7.3
10 10th
10 10th
10 10th
7,8 7.8
10 10th
10 10th
Komponente II Component II
3,7 3.7
3,7 3.7
3,7 3.7
3,7 3.7
- -
- -
- -
5,2 5.2
- -
- -
Oligomer Oligomer
4 4th
4 4th
4 4th
4 4th
4 4th
4 4th
4 4th
4 4th
4 4th
4 4th
Russ Soot
0,02 0.02
- -
0,1 0.1
1 1
0,02 0.02
0,1 0.1
0,5 0.5
0,5 0.5
0,02 0.02
- -
DMAB * DMAB *
- -
- -
- -
- -
- -
- -
- -
- -
0,42 0.42
0,42 0.42
Cobaltnaphthenat Cobalt naphthenate
0,15 0.15
0,15 0.15
0,15 0.15
0,15 0.15
0,15 0.15
0,15 0.15
0,15 0.15
0,15 0.15
0,15 0.15
0,15 0.15
Benzoylperoxid Benzoyl peroxide
0,8 0.8
0,8 0.8
0,8 0.8
0,8 0.8
0,8 0.8
0,8 0.8
0,8 0.8
0,8 0.8
0,75 0.75
0,75 0.75
Ti02 Ti02
- -
- -
- -
- -
- -
- -
- -
- -
6 6
6 6
Sand ca. 85 Sand approx. 85
- -
- -
- -
— -
— -
- -
ca. 82 approx. 82
78,66 78.66
78,66 78.66
Topf zeit Pot time
40 min 40 min
> 4 Tage > 4 days
20 min 20 min
< 2 min <2 min
190 min 190 min
31 min 31 min
5 min 5 min
10-15 min 10-15 min
30 min 30 min
Klebefreiheit Stickiness
1 Tag ca. 6 Tage 1 day about 6 days
2 Tage 2 days
1-2 Std. 1-2 hours
90 min 90 min
500 min 500 min
* DMAB = p-Dimethylaminobenzaldehyd co en * DMAB = p-dimethylaminobenzaldehyde co en
> >
01 01
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
CH 684 795 A5 CH 684 795 A5
Claims (12)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4119646 | 1991-06-14 | ||
| DE4119648 | 1991-06-14 | ||
| DE4119647 | 1991-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH684795A5 true CH684795A5 (en) | 1994-12-30 |
Family
ID=27202591
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1845/92A CH684795A5 (en) | 1991-06-14 | 1992-06-11 | Monomer formulations for the construction industry. |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JP2696039B2 (en) |
| AT (1) | AT398966B (en) |
| AU (1) | AU654717B2 (en) |
| BE (1) | BE1005805A3 (en) |
| CA (1) | CA2071101A1 (en) |
| CH (1) | CH684795A5 (en) |
| DE (1) | DE4218414C2 (en) |
| ES (1) | ES2059235B1 (en) |
| FR (1) | FR2677656B1 (en) |
| GB (1) | GB2256645B (en) |
| IT (1) | IT1255669B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4242356A1 (en) * | 1992-12-15 | 1994-06-16 | Sandoz Ag | Monomer preparations for the construction industry |
| DE19549104A1 (en) * | 1995-12-29 | 1997-07-03 | Remmers Bauchemie Gmbh | Pigmented plastic floor and process for its manufacture |
| NL1005690C2 (en) * | 1997-04-01 | 1998-10-05 | Zijlstra & Co Verf B V | Flexible building filler and sealant composition |
| EP2607438B1 (en) * | 2011-12-21 | 2014-10-01 | Henkel AG & Co. KGaA | Dry bonding acrylate adhesive layers |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2029898C2 (en) * | 1970-06-18 | 1986-01-30 | Karl Ullrich GmbH & Co, 6451 Mainhausen | Coating agent for mineral building materials or asphalt |
| SU424836A1 (en) * | 1971-03-30 | 1974-04-25 | POLYMERBETON MIX | |
| DE2155232B2 (en) * | 1971-11-06 | 1975-11-20 | Vki-Rheinhold & Mahla Ag, 6800 Mannheim | /kTQfc.U.ll QTIQ.QS.-B RT. IQ .U .7 S Manufacture of elements for the construction industry |
| DE2209149A1 (en) * | 1972-02-26 | 1973-09-06 | Roehm Gmbh | PROCESS FOR MANUFACTURING MOLDED BODIES SUBSTANTLY FROM MINERAL BUILDING MATERIALS |
| US4197225A (en) * | 1976-05-19 | 1980-04-08 | Rohm And Haas Company | Polymer concrete compositions and cured products thereof |
| ZA7803231B (en) * | 1976-07-07 | Rohm & Haas | Monomer compositions | |
| US4299761A (en) * | 1979-03-19 | 1981-11-10 | Rohm And Haas Company | Polymer concrete compositions, methods of application thereof, and polymerized products thereof |
| SU835987A1 (en) * | 1979-05-24 | 1981-06-07 | Калушский Филиал Всесоюзного Научно- Исследовательского И Проектногоинститута Галургии | Polymer-concrete mix |
| ZA815786B (en) * | 1980-08-29 | 1982-08-25 | Rohm & Haas | Monomer compositions,polymer concrete compositions containing them and their use |
| US4400413A (en) * | 1980-08-29 | 1983-08-23 | Rohm And Haas Company | Acrylic polymer concrete compositions |
| SU996378A1 (en) * | 1981-07-03 | 1983-02-15 | Калушский Филиал Всесоюзного Научно-Исследовательского И Проектного Института Галургии | Polymeric concrete mix |
| US4460625A (en) * | 1981-07-16 | 1984-07-17 | Rohm And Haas Company | Method of coating and impregnating concrete substrates, and products obtained thereby |
| JPS58204008A (en) * | 1982-05-24 | 1983-11-28 | Hitachi Ltd | Photosensitive resin composition |
| US4932750A (en) * | 1982-12-09 | 1990-06-12 | Desoto, Inc. | Single-coated optical fiber |
| SU1209672A1 (en) * | 1983-12-28 | 1986-02-07 | Центральный научно-исследовательский и проектно-экспериментальный институт промышленных зданий и сооружений | Polymerconcrete mix |
| US4556701A (en) * | 1984-03-30 | 1985-12-03 | Rohm And Haas Company | Impregnant compositions for porous substrates |
| JPS6271573A (en) * | 1985-09-24 | 1987-04-02 | Dainippon Ink & Chem Inc | Actual spot painting and curing method for floor surface |
| JPH0618844B2 (en) * | 1985-11-29 | 1994-03-16 | 日本合成ゴム株式会社 | Liquid radiation curable resin composition |
| SU1465432A1 (en) * | 1987-03-23 | 1989-03-15 | Калушский Филиал Всесоюзного Научно-Исследовательского И Проектного Института Галургии | Polymer-concrete mix composition |
| DE3822202A1 (en) * | 1988-07-01 | 1990-01-04 | Sandoz Ag | Acrylic acid esters and homopolymeric compounds thereof |
| DE3920795C2 (en) * | 1988-07-01 | 1999-06-24 | Mbt Holding Ag | Asymmetric diesters, processes for their preparation and preparations containing them |
| SU1701686A1 (en) * | 1989-07-07 | 1991-12-30 | Калушский Филиал Всесоюзного Научно-Исследовательского И Проектного Института Галургии | Polymer-concrete mixture |
| JPH03265561A (en) * | 1990-03-13 | 1991-11-26 | Hitachi Chem Co Ltd | Production of high-density oxide superconductor |
-
1992
- 1992-06-04 DE DE4218414A patent/DE4218414C2/en not_active Expired - Lifetime
- 1992-06-09 BE BE9200531A patent/BE1005805A3/en not_active IP Right Cessation
- 1992-06-10 GB GB9212306A patent/GB2256645B/en not_active Expired - Lifetime
- 1992-06-10 FR FR9207173A patent/FR2677656B1/en not_active Expired - Lifetime
- 1992-06-11 CH CH1845/92A patent/CH684795A5/en not_active IP Right Cessation
- 1992-06-11 ES ES09201224A patent/ES2059235B1/en not_active Expired - Fee Related
- 1992-06-12 CA CA002071101A patent/CA2071101A1/en not_active Abandoned
- 1992-06-12 IT ITRM920441A patent/IT1255669B/en active IP Right Grant
- 1992-06-12 JP JP4153278A patent/JP2696039B2/en not_active Expired - Lifetime
- 1992-06-12 AT AT0121092A patent/AT398966B/en not_active IP Right Cessation
- 1992-06-12 AU AU18173/92A patent/AU654717B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ITRM920441A1 (en) | 1993-12-12 |
| ITRM920441A0 (en) | 1992-06-12 |
| AU654717B2 (en) | 1994-11-17 |
| ES2059235B1 (en) | 1995-10-01 |
| JPH05239379A (en) | 1993-09-17 |
| DE4218414C2 (en) | 2001-04-05 |
| DE4218414A1 (en) | 1992-12-17 |
| ATA121092A (en) | 1994-07-15 |
| IT1255669B (en) | 1995-11-09 |
| AT398966B (en) | 1995-02-27 |
| ES2059235A1 (en) | 1994-11-01 |
| FR2677656A1 (en) | 1992-12-18 |
| JP2696039B2 (en) | 1998-01-14 |
| AU1817392A (en) | 1992-12-17 |
| FR2677656B1 (en) | 1993-10-22 |
| GB2256645B (en) | 1995-03-15 |
| CA2071101A1 (en) | 1992-12-15 |
| GB2256645A (en) | 1992-12-16 |
| GB9212306D0 (en) | 1992-07-22 |
| BE1005805A3 (en) | 1994-02-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUE | Assignment |
Owner name: SANDOZ AG TRANSFER- MBT HOLDING AG |
|
| PUE | Assignment |
Owner name: CONSTRUCTION RESEARCH & TECHNOLOGY GMBH Free format text: MBT HOLDING AG#VULKANSTRASSE 110#8068 ZUERICH (CH) -TRANSFER TO- CONSTRUCTION RESEARCH & TECHNOLOGYGMBH#DR.-ALBERT-FRANK-STRASSE 32#83308 TROSTBERG (DE) |
|
| PL | Patent ceased |