AT398966B - MONOMER PREPARATIONS FOR THE CONSTRUCTION INDUSTRY - Google Patents
MONOMER PREPARATIONS FOR THE CONSTRUCTION INDUSTRY Download PDFInfo
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- AT398966B AT398966B AT0121092A AT121092A AT398966B AT 398966 B AT398966 B AT 398966B AT 0121092 A AT0121092 A AT 0121092A AT 121092 A AT121092 A AT 121092A AT 398966 B AT398966 B AT 398966B
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- 238000002360 preparation method Methods 0.000 title claims description 26
- 239000000178 monomer Substances 0.000 title claims description 25
- 238000010276 construction Methods 0.000 title description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 12
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000004071 soot Substances 0.000 claims description 7
- 239000006229 carbon black Substances 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 6
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 6
- -1 alicyclic dicarboxylic acid ester Chemical class 0.000 claims description 5
- 239000004567 concrete Substances 0.000 claims description 5
- 239000011159 matrix material Substances 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 229920000570 polyether Polymers 0.000 claims description 4
- 239000004576 sand Substances 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
- 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
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical group CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 claims description 2
- 238000005266 casting Methods 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 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
- 239000002986 polymer concrete Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 229910052723 transition metal Inorganic materials 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 150000002148 esters Chemical class 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
- 101000623895 Bos taurus Mucin-15 Proteins 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 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
- 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
- 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
- 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
- OAKAPFPXXUWHMV-UHFFFAOYSA-N 2-methoxycarbonylcyclohex-3-ene-1-carboxylic acid Chemical compound COC(=O)C1C=CCCC1C(O)=O OAKAPFPXXUWHMV-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
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-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
- 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
- 238000005452 bending Methods 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000001273 butane Substances 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
- 238000005470 impregnation Methods 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
- 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 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 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
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- 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
AT 398 966 BAT 398 966 B
Oie Erfindung betrifft Monomerzubereitungen, die in verschiedenen Bereichen der Bauindustrie eingesetzt verden können, und insbesondere den Zusatz von Russ und/oder von polyfunktionellen Oligomeren zur Verbesserung der Eigenschaften der damit hergestellten Polymermatrix-Kombinationen. Die schnellhärtenden Zubereitungen mit Füllstoffen dienen zur Herstellung von Belägen, Beschichtungen, Gussmassen, 5 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 to 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, 5 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 io aus.Polymer concrete masses, which are produced by 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 their high mechanical strength.
Es wurde nun gefunden, dass die Eigenschaften der erhaltenen Polymerbetonmassen noch wesentlich verbessert verden 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 75 Flammpunkt über 50 *C, die 0,01 bis 7 Gewichtsprozent Russ und/oder polyfunktionelle Oligomere auf Basis von Polyester oder Polyäther/Urethan/Acryiat 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 of 75 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 obtained by curing these preparations Polymer matrix combinations with and without fillers.
Die Mengenangaben für den Russ-Zusatz beziehen sich auf die Menge des Acrylbindemittels und betragen bevorzugt 0,1 bis 3, an meisten bevorzugt 0,1 bis 0,5 Gewichtsprozent Russ mit einer BET-Fläche 20 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 the acrylic binder and are preferably 0.1 to 3, most preferably 0.1 to 0.5 percent by weight of soot with a BET surface area 20 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, bifunktionelle oder polyfunktionelle Polyester bzw. Polyäther/Urethan-Acrylate mit einem Molekulargewicht von 500-2000, bevorzugt 1000-2000 und einer Viskosität von 2.000-100.000 mPa s (bei 25 eC), bevorzugt von 12.000 bis 25 100.000, am meisten bevorzugt von 60-75.000 mPa s. Sie werden durch Einpoiymerisierung 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 2,000-100,000 mPa s (at 25 eC), preferably of 12,000 to 25 100,000, most preferably from 60-75,000 mPas. They are produced by polymerizing acrylic acid or methacrylic acid esters in polyester or polyether / urethanes and have at least two unsaturated bonds which are used to crosslink the usual 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 30 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 30 products are:
Name Firma Struktur MW Viskosität GENOMER T 1600 Rahn AG Zürich aliphatisch Triacrylat -1600 52.000 GENOMERD 1500 B »1 aliphatisch Diacrylat EBECRYL 205 UCB Belgien aromatisch Triacrylat 2,000 30,000 EBECRYL210 ir aromatische Diacrylat 1,500 4,000 EBECRYL1259 tt aliphatisch Triacrylat 2,000 14,000 EBECRYL1290 1» aliphatisch Hexacrylat 1,000 2,000Name Company Structure MW Viscosity GENOMER T 1600 Rahn AG Zurich aliphatic triacrylate -1600 52,000 GENOMERD 1500 B »1 aliphatic diacrylate EBECRYL 205 UCB Belgium aromatic triacrylate 2,000 30,000 EBECRYL210 ir aromatic diacrylate 1,500 4,000 EBECRYL1259 tEC aliphatic 2,000 acrylate 1,000,000 triacrylate 1,000acrylic
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 Methacrylsäure 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. Eine bevorzugte Gruppe solcher Monomere entspricht der allgemeinen Formel IThe 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. A preferred group of such monomers corresponds to the general formula I.
CH2 = C - C -(ORx)n - OR2 I 1 u R 0 worin R Wasserstoff oder Methyl,CH2 = C - C - (ORx) n - OR2 I 1 u R 0 where R is hydrogen or methyl,
Ri eine Alkylengruppe mit 2 bis 6 C-Atomen, n eine ganze Zahl von 1 bis 3 oder Null und R2 einen Rest eines aromatischen oder aiicyclischen Dicarbonsäureesters oder, wenn n = 0, einen Dicyclopentenylrest bedeuten. Solche Acryimonomere haben einen Flammpunkt von mindestens 2R 1 is an alkylene group having 2 to 6 carbon atoms, n is an integer from 1 to 3 or zero and R 2 is a radical of an aromatic or aicyclic dicarboxylic acid ester or, if n = 0, is a dicyclopentenyl radical. Such acrylic monomers have a flash point of at least 2
AT 398 966 B 50' C und bevorzugt über 100 · C.AT 398 966 B 50 'C and preferably over 100C.
Bevorzugt sind solche Ester, in denen R Methyl, Ri eine verzweigte Alkylengruppe mit 3 oder 4 C-Atomen, n die Zahl 1 und Ra den Rest einer Tetrahydrophthalsäure, die ausserdem mit einem einfachen Alkohol wie Methanol oder Aethanol verestert ist, bedeuten.Preferred esters are those in which R is methyl, Ri is a branched alkylene group with 3 or 4 carbon atoms, n is 1 and Ra is the rest 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 in der Gesamtmischung betragen die Acrylate der Formel I (Komponente I) von 20 bis 100 Gewichtsprozent, bevorzugt 50-95 Gewichtsprozent und die einfachen Acrylate (Komponente II) von 8 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 aus.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 in the total mixture are 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 8 to 80 percent by weight, preferably 5-50 percent by weight, if none 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 Uebergangsmetallen 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 Uebergangsmetallen 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 Diisopropylbenzolhydrop-eroxid.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 Uebergangsmetallen sind solche, die die oxydative Aushärtung von trocknenden Oelen 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, Kobalt-acetylacetonat und die entsprechenden Mangansalze.The salts or complexes of transition metals are those which catalyze the oxidative hardening 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, Ν,Ν-Dimethyl- oder Ν,Ν-Diäthylanilin, entsprechende Toluidine 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, Ν, Ν-dimethyl- or Ν, Ν-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 Kataiysatorsystem aus einem Peroxid oder Hydroperoxid, einem aromatischen Amin und einem Uebergangsmetallsalz.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 Poiymerbetonmassen üblich sind. Für Ueberzüge werden Feinaggregate wie Feinsand, eventl. 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 Polymerisationskataiysator mit dem Uebergangsmetallsalz in getrennten Packungen abgegeben, die kurz vor der Anwendung miteinander vermischt werden. Je nach eingesetztem Katalysator kann auch das Kataiysatorsystem (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. 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 Beschichtung 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. However, they can also be used for the impregnation or coating of porous materials, in particular concrete, or for filling cracks. In particular, very resistant floor coverings are produced from these preparations.
Neben einer guten Wasserbeständigkeit und Wärmefestigkeit zeichnen sich die erhaltenen Poiymerbetonmassen 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 masses obtained are particularly notable for increased impact strength, compressive and flexural tensile strength and 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. 3In the following examples, parts are parts by weight and percentages are percentages by weight. The temperatures are given in degrees Celsius. 3rd
AT 398 966 BAT 398 966 B
Die Komponente I ist ein Ester des Tetrahydrophthalsäuremonomethylesters und Hydroxypropylmetha-crylat. Die Komponente II ist ein Hydroxypropylmethacrylat. Das Oligomer ist das Produkt GENOMER T 1200 der Firma Rahn, Zürich.Component I is an ester of tetrahydrophthalic acid monomethyl ester 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 s DEGUSSA).The soot used is a furnace soot with a BET surface area of 80 m2 / g (Printex 300 from s 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. 70 75 20 25 30 35 40 45 50 4 55 5 10 75 20 25 30 35 40 45 50The 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. 70 75 20 25 30 35 40 45 50 4 55 5 10 75 20 25 30 35 40 45 50
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•3 e w •H CO £ <P © CS m 1 cs pH •3 w «3 CO C-| pH © «n A. Λ bä C 3• 3 e w • H CO £ < P © CS m 1 cs pH • 3 w «3 CO C- | pH © «n A. Λ bä C 3
© U Cr' 3 N c m O ©. ε o 24 W o cs e c -o M o fH pH ✓*N M p ΊΖ. X o i /V s 0 «4 s M α XJ “D r—I <5 cu -β s C*S C “· 3 p pH M c ·» C3 © c AJ is Λ 03 © 0} I w o pH o 03 N } N •C“ N c. erj «3 N ε Lj U o SH 03 tz i*£ CS ·* C3 ·» 5 O e © ZS © 3 © O 24 2 © s 2 © >«✓ © o u er 43 CJ /—f 5 55 5 10 15 20 35 40 45 50© U Cr '3 N c m O ©. ε o 24 W o cs e c -o M o fH pH ✓ * N M p ΊΖ. X oi / V s 0 «4 s M α XJ“ D r — I <5 cu -β s C * SC “· 3 p pH M c ·» C3 © c AJ is Λ 03 © 0} I wo pH o 03 N} N • C “N c. erj «3 N ε Lj U o SH 03 tz i * £ CS · * C3 ·» 5 O e © ZS © 3 © O 24 2 © s 2 © > «✓ © ou er 43 CJ / —f 5 55 5 10 15 20 35 40 45 50
AT 398 966 B Ό tO m CS fs. fH <3 • • • <T N C\ — c c- o O a . w es O \n CS m O rH * » • e Ό CO %3 o « * <e C. o o <y « cs •c «Ί cs m m CO «ft • • CO ST <n ö <3 «5 Ci o ü o 0 • e. n a <s V o t—i <-*. c. 03 «J CS «5 E* csAT 398 966 B Ό tO m CS fs. fH < 3 • • • < T N C \ - c c- o O a. w es O \ n CS m O rH * »• e Ό CO% 3 o« * < e C. oo < y «cs • c« Ί cs mm CO «ft • • CO ST < n ö < 3 «5 Ci o ü o 0 • e. n a < s V o t — i < - *. c. 03 «J CS« 5 E * cs
Ci « cs CO r-( m in in o «m o -« ri r- o *-> O «n r» cs' O rl r> η o rs >v” O n cs η α in o Γ·* f—i ·* « * in cs - o e « cs o CJ o 'S o m cs m cs m r-i CI σν o ψ ·« o cs o Ä e rH a C3 U*l -fl vo m cs in CS O © . « m O CS o « CS rH o a «c m M SÄ ec o i* « JO 3 es u -»ft « r“( ω ;-i o > m : I—( »s m in t r-l es · - - fl o o o \o cs • rt o m η = w 'S •H M 3 Tft r-l x-% c; K-i M X 1 “ «-> o o 5 5 £3 O a 14 £ »rt «j 4H c. CD Ti "0 JS 3 5 0 ¢5 e fl. r*i -fl s Γ3 c-i c fl O 225 09 s i-f >. 3 « O w 1 ω © o o f—Γ O » SC 1 s ST eü c. £. CO Γ3 N ~ *-H o rH iH .Ä C w C3 fl •ft «C o o rS O 3 o 3 o 3 o CJ Q o a z © C? w w UlegezugCestißkoit Druckfestigkei t 6 55Ci «cs CO r- (m in in o« mo - «ri r- o * - > O« nr »cs' O rl r > η o rs > v” O n cs η α in o Γ · * f — i · * «* in cs - oe« cs o CJ o 'S om cs m cs m ri CI σν o ψ · «o cs o Ä e rH a C3 U * l -fl vo m cs in CS O © . «M O CS o« CS rH oa «cm M SÄ ec oi *« JO 3 es u - »ft« r “(ω; -io > m: I— (» sm in t rl es · - - fl ooo \ o cs • rt om η = w 'S • HM 3 Tft rl x-% c; Ki MX 1 “« - > oo 5 5 £ 3 O a 14 £ »rt« j 4H c. CD Ti " 0 JS 3 5 0 ¢ 5 e fl. R * i -fl s Γ3 ci c fl O 225 09 s if >. 3 «O w 1 ω © oof — Γ O» SC 1 s ST eü c. £. CO Γ3 N ~ * -H o rH iH .Ä C w C3 fl • ft «C oo rS O 3 o 3 o 3 o CJ Q oaz © C? Ww UlegzugCestißkoit Druckfestigkeit 6 55
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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 |
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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 |
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
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- 1992-06-09 BE BE9200531A patent/BE1005805A3/en not_active IP Right Cessation
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- 1992-06-10 FR FR9207173A patent/FR2677656B1/en not_active Expired - Lifetime
- 1992-06-11 ES ES09201224A patent/ES2059235B1/en not_active Expired - Fee Related
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CH684795A5 (en) | 1994-12-30 |
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