EP1940752A2 - Carbonsäure-derivate, verfahren zu ihrer herstellung sowie deren verwendung - Google Patents

Carbonsäure-derivate, verfahren zu ihrer herstellung sowie deren verwendung

Info

Publication number
EP1940752A2
EP1940752A2 EP06805482A EP06805482A EP1940752A2 EP 1940752 A2 EP1940752 A2 EP 1940752A2 EP 06805482 A EP06805482 A EP 06805482A EP 06805482 A EP06805482 A EP 06805482A EP 1940752 A2 EP1940752 A2 EP 1940752A2
Authority
EP
European Patent Office
Prior art keywords
acid
reactive component
diglycidyl ether
carboxylic acid
fatty acid
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Withdrawn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
EP06805482A
Other languages
German (de)
English (en)
French (fr)
Inventor
Stefan Ingrisch
Gerhard Albrecht
Stefan Thaler
Mathias Bauer
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.)
Construction Research and Technology GmbH
Original Assignee
Construction Research and Technology GmbH
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 Construction Research and Technology GmbH filed Critical Construction Research and Technology GmbH
Publication of EP1940752A2 publication Critical patent/EP1940752A2/de
Withdrawn legal-status Critical Current

Links

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
    • C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
    • C04B24/24—Macromolecular compounds
    • C04B24/26—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C04B24/2664—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of ethylenically unsaturated dicarboxylic acid polymers, e.g. maleic anhydride copolymers
    • 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
    • C04B24/24—Macromolecular compounds
    • C04B24/26—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C04B24/2652—Nitrogen containing polymers, e.g. polyacrylamides, polyacrylonitriles
    • 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
    • C04B24/24—Macromolecular compounds
    • C04B24/26—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C04B24/2652—Nitrogen containing polymers, e.g. polyacrylamides, polyacrylonitriles
    • C04B24/2658—Nitrogen containing polymers, e.g. polyacrylamides, polyacrylonitriles containing polyether side chains
    • 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
    • C04B24/24—Macromolecular compounds
    • C04B24/26—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C04B24/2664—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of ethylenically unsaturated dicarboxylic acid polymers, e.g. maleic anhydride copolymers
    • C04B24/267—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of ethylenically unsaturated dicarboxylic acid polymers, e.g. maleic anhydride copolymers containing polyether side chains
    • 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
    • C04B24/24—Macromolecular compounds
    • C04B24/28—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C04B24/281—Polyepoxides
    • 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
    • C04B24/24—Macromolecular compounds
    • C04B24/28—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C04B24/32—Polyethers, e.g. alkylphenol polyglycolether
    • 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
    • C04B24/40—Compounds containing silicon, titanium or zirconium or other organo-metallic compounds; Organo-clays; Organo-inorganic complexes
    • C04B24/42—Organo-silicon compounds
    • 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
    • C04B2103/00—Function or property of ingredients for mortars, concrete or artificial stone
    • C04B2103/0045—Polymers chosen for their physico-chemical characteristics
    • C04B2103/0061—Block (co-)polymers
    • 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
    • C04B2111/20—Resistance against chemical, physical or biological attack
    • C04B2111/21—Efflorescence resistance
    • 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
    • C04B2111/20—Resistance against chemical, physical or biological attack
    • C04B2111/27—Water resistance, i.e. waterproof or water-repellent materials

Definitions

  • Carboxylic acid derivatives process for their preparation and their use
  • the present invention relates to carboxylic acid derivatives, to processes for their preparation and to their use as additives for cementitious building materials (such as, for example, concrete or mortar), which is used in particular for mass hydrophobization and / or suppression of efflorescence on surfaces of hardened cementitious building materials ,
  • a well-known problem with cement-based building materials is the occurrence of so-called efflorescence, where a distinction is made between primary and secondary efflorescence.
  • the former are already formed during curing, for example, in concrete, wherein the capillaries of the fresh concrete are filled with an aqueous solution of the water-soluble substances of the cement, essentially calcium hydroxide.
  • the calcium hydroxide on the concrete surface reacts with the carbon dioxide in the air to form sparingly soluble calcium carbonate.
  • the precipitation of calcium carbonate means that the calcium hydroxide concentrate at the capillary mouth is lower than inside the capillaries. Therefore, new calcium hydroxide is constantly passing through diffusion from the deeper layers of the concrete to the capillary mouth and in turn reacts with CO 2
  • secondary efflorescence usually last 1 to 2 years, the cause being the slow formation of water-soluble calcium bicarbonate from calcium carbonate. Since the visual appearance of such efflorescence-affected components is severely impaired, especially in colored concrete products, there has been no lack of attempts to prevent or suppress this efflorescence by various means.
  • DE 199 05 488 A1 discloses a powdery polymer composition based on polyether carboxylates which contains a water-soluble polymer and a finely divided mineral carrier material.
  • DE 4326 772 A1 discloses reaction products of olefinically unsaturated carboxylic acids and polyetherols for use as demulsifiers for crude oil emulsions.
  • DE 31 36 213 A1 discloses bis esters of alkenylsuccinic acids and ethylene oxide-propylene oxide block polymers and their use as demulsifiers for oil / water emulsions, as corrosion inhibitors and as dispersants for dyes.
  • DE 695 30 032 T2 discloses a process for demulsifying water-in-oil emulsions using polyalkylene glycol derivatives.
  • GB 768 790 discloses organosiloxanes and their use as lubricants, corrosion inhibitors and emulsifiers.
  • EP 0 281 838 A2 discloses sulfosuccinamic acids of polyoxypropylenediamines and their use as emulsifiers.
  • EP 0 291 073 B1 discloses a cement additive comprising a copolymer of a polyoxyalkylene derivative and maleic anhydride, a hydrolysis product of the copolymer or a salt of the hydrolysis product.
  • the present invention therefore an object of the invention to provide a means for preventing efflorescence on surfaces of hardened cementitious building materials and / or mass hydrophobization, which does not have the disadvantages of the prior art, but effectively and reliably prevents the efflorescence of cementitious building materials.
  • This object is achieved by the use of a carboxylic acid derivative according to claim 1, in particular by a carboxylic acid derivative according to claim 13.
  • a process for producing the carboxylic acid derivative according to claim 13 is defined in claim 22. Further advantageous embodiments of the invention are defined in the dependent claims.
  • the carboxylic acid derivatives according to the invention are obtainable by reacting an unsaturated dicarboxylic acid anhydride (A) with a hydrophobic reactive component (B) which has at least one group reactive toward carboxylic anhydrides and an average molecular weight of from 200 to 50,000 daltons.
  • the unsaturated dicarboxylic anhydride used are preferably maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, dimethylmaleic anhydride, methylsuccinic anhydride and 2,2-dimethylsuccinic anhydride.
  • hydrophobic reactive component (B) are six classes of compounds selected from the group (B) (i), (B) (U), (B) (Ui), (B) (iv), (B) (v) and ( B) (vi), in question.
  • the reactive component (B) (I) consists of a polydimethylsiloxane of the general formula (I)
  • Reactive component (B) (U) may be a polypropylene glycol of general formula (IIa) (IIa) and / or a polypropylene glycol based on a glycerol ether of the general formula (IIb)
  • a, b, c and d are independently from 1 to 150.
  • the reactive component (B) (Ui) represents either a polyoxyalkyleneamine of the formula (IIIa)
  • the reactive component (B) (iv) is a polyalkylene glycol based on alkylenediamines of the general formula (IV)
  • alkylenediamines here preferably 1, 6-hexamethylenediamine, 1, 8-octamethylenediamine, 1, 10-diaminodecane and 1, 12-diaminododecane used.
  • the reactive component (B) (v) consists of a triglyceride, which is composed of at least one hydroxy fatty acid.
  • fatty acids ricinoleic acid, cerebronic acid, nemotic acid or 12-hydroxystearic acid are used. If necessary, the
  • Hydroxy fatty acid be etherified with 1 to 100 moles of an ethylene oxide derivative.
  • the reactive component (B) (vi) can be an epoxy derivative which is prepared by reacting a di-, TnV or tetraglycidyl component (C) (i) with an optionally unsaturated reactive component (C) (U) consisting of a C 8 -C 2S fatty acid, a Cs-C 28 -alcohol or a C 8 -C 28 -secondary amine.
  • Glycidyl compounds (C) which are selected from the group consisting of cyclohexanedimethanol diglycidyl ether, glycerol triglycidyl ether, neopentyl glycol diglycidyl ether, pentaerythritol tetraglycidyl ether, 1,6-hexanediol diglycidyl ether, polypropylene glycol are particularly advantageously used - diglycidyl ether, polyethylene glycol diglycidyl ether, Trimethyiolpropan- triglycidyl ether, bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, 4,4'-methylenebis (N, N-diglycidylaniline), tetraphenylolethane glycidyl ether, N, N-diglycidylaniline, diethylene glycol diglycidyl ether, 1, 4 Butaned
  • the reactive component (C) (U) consists of a C 8 -C 28 fatty acid, a C 8 -C 8 -alcohol or a C 8 -C 28 -secondary amine, wherein the
  • Reactive component may have saturated or unsaturated radicals.
  • fatty acids are tall oil fatty acid, stearic acid, palmitic acid, sunflower oil fatty acid, coconut oil fatty acid (C 8 -C 18 ), coconut oil fatty acid (C 12 -C 18), soybean oil fatty acid, linseed oil fatty acid, dodecanoic acid, oleic acid, linoleic acid, palm kernel oil fatty acid, palm oil fatty acid, linolenic acid and / or arachidonic acid are to be regarded as preferred.
  • C 8 -C 28 alcohols especially 1-eicosanol, 1-octadecanol, 1-hexadecanol, 1-tetradecanol, 1-dodecanol, 1-decanol and 1-octanol have proven successful.
  • secondary amines with Cs-C 28 -C atoms particularly the alkyl amines from the group 2-ethylhexylamine, dipentylamine, dihexylamine, dioctylamine, bis (2-ethylhexyl) amine, N-methyloctadecylamine and didecylamine are used.
  • the reactive component (B) (vi) or its preparation are known according to the prior art (cf., for example, the German patent application DE 10 2005 022 852).
  • Dicarboxylic anhydride (A) and the hydrophobic reactive component (B) can be varied within wide limits, but it has proved to be particularly advantageous that the molar ratio of the unsaturated dicarboxylic anhydride (A) to the reactive component (B) 0.1 to 1, MoI ( A) per mole of the reactive group of component (B).
  • the preparation of the carboxylic acid derivatives according to the invention is relatively unproblematic.
  • the unsaturated dicarboxylic anhydride (A) is reacted with the reactive component (B) without solvent in the temperature range from 20 to 150 ° C., if appropriate in the presence of a catalyst.
  • a catalyst here is preferably an alkali or alkaline earth metal salt of an organic acid, such as. As sodium or potassium acetate used.
  • the carboxylic acid derivatives used according to the invention are outstandingly suitable for the mass hydrophobization of cementitious construction materials and / or for the suppression of efflorescence on surfaces of hardened cementitious building materials.
  • the carboxylic acid derivatives are the uncured cementitious building materials in an amount from 0.01 to 5 wt .-%, based on the cement content added.
  • cementitious building materials according to the present invention all concrete and mortar systems are to be considered, which may contain lime, gypsum or anhydrite as the main binder cement and as a minor constituent.
  • the carboxylic acid derivatives used in the invention are added directly to the prepared cementitious building materials.
  • the additives used according to the invention may be added to the mixing water or residual water in emulsified form with the aid of external emulsifiers (for example ethoxylated compounds such as fatty acid ethoxylate, ethoxylated castor oil or ethoxylated fatty amine).
  • the carboxylic acid derivatives proposed according to the invention are outstandingly suitable as agents for the prevention or suppression of
  • Example 1 Prepare 100 g (0.050 mol) of polypropylene glycol 2000 (from Aldrich) at room temperature in a reaction vessel, add 11. 03 g (0.1125 mol) of maleic anhydride (from Aldrich) and then add 0.16 g (0.002 mol) of sodium acetate ( Fa. Aldrich). The reaction space is purged with nitrogen and the reaction mixture is heated to 80 0 C. At this temperature is held for 5h, then cooled. This gives a slightly orange, slightly viscous liquid.
  • reaction product from Ex. 1 100 g of the reaction product from Ex. 1 are emulsified in 300 g of water and neutralized with 10% NaOH solution.
  • Example 2 175 g (0.203 mol) of an aminoalkylpolydimethylsiloxane (trade name: Tegomer A-Si 2122, from Tego) are initially introduced at room temperature in a reaction vessel, 43.1 g (0.44 mol) of maleic anhydride (Aldrich) are added and then 0, Add 67 g (0.008 mol) of sodium acetate (Aldrich). The reaction space is purged with nitrogen and the reaction mixture is heated to 80 0 C. At this temperature is held for 5h, then cooled. This gives a slightly brownish, slightly viscous liquid.
  • an aminoalkylpolydimethylsiloxane (trade name: Tegomer A-Si 2122, from Tego) are initially introduced at room temperature in a reaction vessel, 43.1 g (0.44 mol) of maleic anhydride (Aldrich) are added and then 0, Add 67 g (0.008 mol) of sodium acetate (Aldrich). The reaction space
  • reaction product from Ex. 2 100 g of the reaction product from Ex. 2 are emulsified in 400 g of water and neutralized with 10% NaOH solution.
  • reaction product from Ex. 3 100 g of the reaction product from Ex. 3 are emulsified in 400 g of water and neutralized with 10% NaOH solution.
  • reaction product from Ex. 5 100 g of the reaction product from Ex. 5 are emulsified in 400 g of water and neutralized with 10% NaOH solution.
  • reaction product from Ex. 6 100 g of the reaction product from Ex. 6 are emulsified in 400 g of water and neutralized with 10% -KOH solution. A clear red slightly viscous 20% aqueous solution is obtained.
  • Example 7 A 100 g of the reaction product from Ex. 7 are emulsified in 400 g of water and neutralized with 10% -KOH solution. This gives a milky brownish slightly viscous 20% aqueous solution.
  • Example 8A 100 g of the reaction product from Ex. 8 are emulsified in 400 g of water and neutralized with 10% NaOH solution. A clear brownish slightly viscous 20% aqueous solution is obtained.
  • reaction product from Ex. 9 100 g of the reaction product from Ex. 9 are emulsified in 400 g of water and neutralized with 10% NaOH solution.
  • the specimens are prepared by the following method and tested for their efflorescence: According to the standard, a mixture (11 kg) is prepared in a forced mixer according to the following recipe, wherein all aggregates are first dry-mixed for 10 sec. Then the default water is added and mixed for 2 min; then adding the residual water, mixing time 2 min. The additive is added to the residual water:
  • the additive is used in different dosages based on the cement in the mixture and added to either the residual water or the concrete mix.
  • the details of the dosage of the additive always refer to solid "additive" to solid "cement”.
  • the water content of the additive is subtracted from the amount of mixing water.
  • the dosages give the solid of the additive based on the

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  • Chemical & Material Sciences (AREA)
  • Ceramic Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Structural Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Curing Cements, Concrete, And Artificial Stone (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Polyamides (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP06805482A 2005-10-27 2006-10-25 Carbonsäure-derivate, verfahren zu ihrer herstellung sowie deren verwendung Withdrawn EP1940752A2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005051375A DE102005051375A1 (de) 2005-10-27 2005-10-27 Carbonsäure-Derivate, Verfahren zu ihrer Herstellung sowie deren Verwendung
PCT/DE2006/001885 WO2007048396A2 (de) 2005-10-27 2006-10-25 Carbonsäure-derivate, verfahren zu ihrer herstellung sowie deren verwendung

Publications (1)

Publication Number Publication Date
EP1940752A2 true EP1940752A2 (de) 2008-07-09

Family

ID=37912653

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06805482A Withdrawn EP1940752A2 (de) 2005-10-27 2006-10-25 Carbonsäure-derivate, verfahren zu ihrer herstellung sowie deren verwendung

Country Status (9)

Country Link
US (1) US20080319217A1 (pt)
EP (1) EP1940752A2 (pt)
JP (1) JP2009516009A (pt)
BR (1) BRPI0617776A2 (pt)
CA (1) CA2627009A1 (pt)
DE (2) DE102005051375A1 (pt)
EC (1) ECSP088391A (pt)
MX (1) MX2008005361A (pt)
WO (1) WO2007048396A2 (pt)

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RU2634311C2 (ru) 2012-08-13 2017-10-25 Констракшн Рисёрч Энд Текнолоджи Гмбх Композиция ускорителя твердения для цементных композиций
EP2886580A1 (en) 2013-12-20 2015-06-24 Construction Research & Technology GmbH Additive for rheology improvement of inorganic binders
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KR20180023887A (ko) 2015-03-25 2018-03-07 캔들-라이트 컴퍼니, 엘엘씨 다중불포화도가 낮은 식물성유 및 젤화제를 포함하는 양초 제품
JP6873136B2 (ja) 2015-12-17 2021-05-19 コンストラクション リサーチ アンド テクノロジー ゲーエムベーハーＣｏｎｓｔｒｕｃｔｉｏｎ Ｒｅｓｅａｒｃｈ ＆ Ｔｅｃｈｎｏｌｏｇｙ ＧｍｂＨ 重縮合物に基づく減水剤

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US20080319217A1 (en) 2008-12-25
WO2007048396A3 (de) 2008-06-19
DE112006003526A5 (de) 2008-09-25
WO2007048396A2 (de) 2007-05-03
MX2008005361A (es) 2009-03-02
DE102005051375A1 (de) 2007-05-03
BRPI0617776A2 (pt) 2011-08-09
ECSP088391A (es) 2008-05-30
JP2009516009A (ja) 2009-04-16
CA2627009A1 (en) 2007-05-03

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