Polycondensation product based on aromatic compounds, method for the preparation and use thereof

Abstract

Proposed is a polycondensation product comprising as monomer components at least one aryl polyoxyalkylene ether, at least one vicinally disubstituted aromatic compound, at least one aldehyde and also optionally further aromatic compounds; processes for preparing same, and also use thereof as dispersant for aqueous suspensions of inorganic binders and as grinding assistant for inorganic binders.

1 . A polycondensation product comprising as monomer components:
 A) at least one aryl polyoxyalkylene ether of the formula (I)   
       
         
           
           
               
               
           
         
         
           where 
           Ar is an aryl group, 
           R 1  and R 2  each independently of one another are selected from H, methyl and ethyl, with optionally at least one of the groups R 1  and R 2  being H, 
           m is an integer from 1 to 300 and 
           R 3  is selected from the group consisting of H, alkyl, aryl, aralkyl, alkaryl, phosphate, and also mixtures thereof; 
         
         B) at least one aromatic compound of the formula (II), 
       
       
         
           
           
               
               
           
         
         
           where R 4  and R 5  each independently of one another are selected from H, R 8 , OH, OR 8 , C(O)R 8 , COOH, COOR 8 , SO 3 H, SO 3 R 8  and NO 2  and also alkali metal salts, alkaline earth metal salts and ammonium salts thereof, or together are a further fused-on ring, where R 8  each independently is selected from the group consisting of alkyl, aryl, aralkyl, alkaryl, and R 6  and R 7  each independently of one another are selected from OH, OR 9 , C(O)R 9 , COOH and COOR 9  and also alkali metal salts and alkaline earth metal salts and ammonium salts thereof, where R 9  each independently is selected from the group consisting of alkyl, aryl, aralkyl, alkaryl; 
         
         C) at least one aldehyde; and also optionally 
         D) at least one further aromatic compound, selected from the group consisting of phenol, 2-phenoxyethanol, 2-phenoxyethyl phosphate and phosphonate, 2-phenoxyacetic acid, 2-(2-phenoxyethoxy)ethanol, 2-(2-phenoxyethoxy)ethyl phosphate and phosphonate, 2-[4-(2-hydroxyethoxy)phenoxy]ethyl phosphate and phosphonate, 2-[4-(2-phosphonatooxyethoxy)phenoxy]ethyl phosphate and phosphonate, methoxyphenol, phenolsulphonic acid, furfuryl alcohol, and also mixtures thereof. 
       
     
     
         2 . The polycondensation product according to  claim 1 , characterized in that the group Ar is an aryl group having 6 to 10 carbon atoms in the ring system, optionally a phenyl group or a naphthyl group. 
     
     
         3 . The polycondensation product according to  claim 1 , characterized in that m is an integer from 3 to 280, optionally from 10 to 160 and further optionally from 12 to 120. 
     
     
         4 . The polycondensation product according to  claim 1 , characterized in that R 3  is selected from the group consisting of H, C 1-10  alkyl, C 6-10  aryl, C 7-11  aralkyl, C 7-11  alkaryl and phosphate. 
     
     
         5 . The polycondensation product according to  claim 3 , characterized in that the oxyalkylene groups of the aryl polyoxyalkylene ether of the formula (I) are selected from ethylene oxide groups and/or propylene oxide groups, which are arranged randomly, alternatingly, graduatedly and/or blockwise along the chain. 
     
     
         6 . The polycondensation product according to  claim 3 , characterized in that the aryl polyoxyalkylene ether of the formula (I) is a polyethylene glycol monophenyl ether of the formula (III) 
       
         
           
           
               
               
           
         
       
       where m has the specified definition. 
     
     
         7 . The polycondensation product according to  claim 6 , characterized in that the polyethylene glycol monophenyl ether of the formula (III) is a mixture with different values for m within the specified definition. 
     
     
         8 . The polycondensation product according to  claim 1 , characterized in that R 8  and R 9  each independently are selected from H, C 1-10  alkyl, C 6-10  aryl, C 7-11  aralkyl and C 7-11  alkaryl. 
     
     
         9 . The polycondensation product according to  claim 1 , characterized in that the aromatic compound of the formula (II) is selected from the group consisting of benzene-1,2-diol, benzene-1,2,3-triol, 2-hydroxybenzoic acid, 2,3- and 3,4-dihydroxybenzoic acid, 3,4,5-trihydroxybenzoic acid, phthalic acid, 3-hydroxyphthalic acid, 2,3- and 3,4-dihydroxybenzenesulphonic acid, 1,2- and 2,3-dihydroxynaphthalene, 1,2- and 2,3-dihydroxynaphthalene-5- or -6-sulphonic acid, and also mixtures thereof. 
     
     
         10 . The polycondensation product according to  claim 1 , characterized in that the aldehyde component C) is selected from the group consisting of formaldehyde, paraformaldehyde, glyoxylic acid, benzaldehyde, benzaldehydesulphonic acid, benzaldehydedisulphonic acid, vanillin and isovanillin, and also mixtures thereof. 
     
     
         11 . The polycondensation product according to  claim 1 , characterized in that the molar ratio of components C:(A+B) is from 1:3 to 3:1, optionally 1:2 to 2:1 and further optionally 1:0.9 to 1:1.1. 
     
     
         12 . The polycondensation product according to  claim 1 , characterized in that the molar ratio of components A:B is from 1:10 to 10:1, optionally 1:7 to 5:1 and further optionally 1:5 to 3:1. 
     
     
         13 . The polycondensation product according to  claim 1 , characterized in that the molar ratio of components D:(A+B) is from 0 to 3:1, optionally 0 to 2:1 and further optionally 0 to 1:1. 
     
     
         14 . The polycondensation product according to  claim 1  in the form of a comb polymer with novolak structure. 
     
     
         15 . The polycondensation product according to  claim 1 , having a molecular weight in the range from 1000 to 100 000, optionally 2000 to 75 000 and further optionally 4000 to 50 000 g/mol. 
     
     
         16 . A process for preparing the polycondensation product according to  claim 1 , characterized in that components A), B), C) and optionally D) are subjected to polycondensation in aqueous solution at a temperature of 20 to 140° C. under a pressure of 1 to 10 bar. 
     
     
         17 . The process according to  claim 16 , characterized in that the polycondensation takes place in the presence of an acidic catalyst optionally selected from the group consisting of sulphuric acid, methanesulphonic acid, p-toluenesulphonic acid, oxalic acid and phosphoric acid, and also mixtures thereof. 
     
     
         18 . The process according to  claim 16 , characterized in that after conclusion of the polycondensation, the reaction mixture is subjected to an aftertreatment at a pH of 8.0 to 13.0, at a temperature of 60 to 120° C. and optionally under a pressure of 0.01 to 0.9 bar. 
     
     
         19 . The process according to  claim 18 , characterized in that the pH is adjusted by addition of an aqueous alkali, optionally NaOH, and the salts formed during the neutralization are removed. 
     
     
         20 . A process of utilizing the polycondensation product according to  claim 1  as a dispersant for aqueous suspensions of inorganic binders selected from the group encompassing hydraulic binders, latent hydraulic binders, pozzolanic binders, alkali-activated and/or alkali-activatable aluminosilicate binders, and also mixtures thereof. 
     
     
         21 . The process according to  claim 20 , characterized in that:
 the hydraulic binders are selected from cements, Portland cements and aluminate cements, and also mixtures thereof,   the latent hydraulic binders are selected from industrial and/or synthetic slags, blast furnace slag, slag sand, ground slag sand, electrothermic phosphorus slag, stainless-steel slag, and also mixtures thereof,   and the pozzolanic binders are selected from amorphous silica, precipitated silica, pyrogenic silica, microsilica, finely ground glass, fly ash, brown-coal fly ash, mineral-coal fly ash, metakaolin, natural pozzolans, tuff, trass and volcanic ash, natural zeolites, and synthetic zeolites, and also mixtures thereof.   
     
     
         22 . The process according to  claim 21 , characterized in that the alkali-activated aluminosilicate binders comprise the latent hydraulic and/or the pozzolanic binders and also alkaline activators, optionally aqueous solutions of alkali metal carbonates, alkali metal fluorides, alkali metal hydroxides, alkali metal aluminates, alkali metal silicates, soluble waterglass, and also mixtures thereof. 
     
     
         23 . The process according to  claim 20  as a constituent of construction material formulations and/or construction material products on-site concrete, pre-cast concrete parts, concrete ware, cast concrete stones in-situ concrete, air-placed concrete, ready-mixed concrete, construction adhesives adhesives for thermal insulation composite systems, concrete repair systems, one-component sealing slurries, two-component sealing slurries, screeds, filling and levelling compounds, tile adhesives, renders, adhesives, sealants, coating systems optionally for tunnels, wastewater channels, splash protection and condensate lines, dry mortars, joint grouts, drainage mortars and/or repair mortars. 
     
     
         24 . A process of utilizing the polycondensation product according to  claim 1  as a grinding assistant for inorganic binders selected from the group encompassing hydraulic binders, latent hydraulic binders and pozzolanic binders and/or alkali-activatable aluminosilicate binders, and also mixtures thereof, wherein
 the latent hydraulic binders are selected from industrial and/or synthetic slags, blast furnace slag, slag sand, ground slag sand, electrothermic phosphorus slag, stainless-steel slag, and also mixtures thereof, 
 and the pozzolanic binders are selected from amorphous silica, precipitated silica, pyrogenic silica, microsilica, finely ground glass, fly ash, brown-coal fly ash, mineral-coal fly ash, metakaolin, natural pozzolans, tuff, trass, volcanic ash, natural zeolites, and synthetic zeolites, and also mixtures thereof. 
 
     
     
         25 . The process according to  claim 20  together with further auxiliaries selected from the group encompassing glycols, polyalcohols, amine alcohols, organic acids, amino acids, sugars, molasses, organic salts, inorganic salts, polycarboxylate ethers, naphthalenesulphonate, melamine/formaldehyde polycondensation products, lignosulphonate, and also mixtures thereof.