Dialdimine, emulsion containing dialdimine, and bicomponent polyurethane composition, and the use thereof

Abstract

The present invention relates to dialdimines of the formula (I) and emulsions and uses thereof. In particular, they can be used for the preparation of pasty curing agent or accelerator components for polymers having isocyanate groups, which lead to very high early strength, which have good flow behaviour on pumping and which can be formulated without VOC solvents, in particular without N-alkylpyrrolidones. These components can be homogeneously or inhomogeneously mixed in an outstanding manner, in particular in a laminar manner, with components which contain polyurethane polymers having isocyanate groups, the two-component compositions thus obtained curing rapidly, having extremely high early strength and remaining without annoying weaknesses.

1 . Dialdimine of the formula (I) 
     
       
         
         
             
             
         
       
       in which R represents the radical of an aldehyde ALD after removal of an aldehyde group; 
       A represents the radical of a diamine DA having two primary aliphatic amino groups after removal of the two primary aliphatic amino groups; 
       Q represents the radical of a diisocyanate DI after removal of both isocyanate groups; 
       n represents 0 or represents an integer from 1 to 15; and 
       in which A and R have no groups which are reactive with isocyanate groups in the absence of water. 
     
   
   
       2 . Dialdimine according to  claim 1 , wherein R represents the radical of the formula (II) 
     
       
         
         
             
             
         
       
       in which R 1  and R 2    
       either independently of one another each represent a monovalent hydrocarbon radical having 1 to 12 C atoms; 
       or together represent a divalent hydrocarbon radical having 4 to 20 C atoms, which is part of an optionally substituted, carbocyclic ring having 5 to 8 C atoms; 
       R 3  represents a hydrogen atom or represents an alkyl or arylalkyl group; 
       R 4    
       represents a hydrocarbon radical optionally containing heteroatoms and having 1 to 30 C atoms; 
       or represents a radical of the formula (III′) 
     
     
       
         
         
             
             
         
       
       in which R 5    
       represents a linear or branched alkyl radical having 1 to 30 C atoms, optionally having cyclic moieties and optionally having at least one heteroatom; 
       or represents a mono- or polyunsaturated linear or branched hydrocarbon radical having 1 to 30 C atoms. 
     
   
   
       3 . Dialdimine according to  claim 2 , wherein R 4    represents a hydrocarbon radical optionally containing heteroatoms and having 11 to 30 C atoms;   or represents a radical of the formula (III′)   
     
       
         
         
             
             
         
       
       in which R 5    
       represents a linear or branched alkyl radical having 11 to 30 C atoms, optionally having cyclic moieties and optionally having at least one heteroatom; 
       or represents a mono- or polyunsaturated linear or branched hydrocarbon radical having 11 to 30 C atoms. 
     
   
   
       4 . Dialdimine according to  claim 1 , wherein the radicals A and R have no hydroxyl groups, no primary or secondary amino groups, no mercapto groups and no other groups having active hydrogen. 
   
   
       5 . Dialdimine according to  claim 1 , wherein the diisocyanate DI is a polyurethanepolymer P having isocyanate groups. 
   
   
       6 . Dialdimine according to  claim 5 , wherein the polyurethanepolymer P having isocyanate groups is prepared from the reaction of at least one diol with at least one monomeric diisocyanate. 
   
   
       7 . Dialdimine according to  claim 6 , wherein the monomeric diisocyanate is an aromatic diisocyanate. 
   
   
       8 . Dialdimine according to  claim 6 , wherein the diol is a polyoxyalkylenediol. 
   
   
       9 . Dialdimine according to  claim 1 , wherein the dialdimine of the formula (I) has a molecular weight of 1000 to 30 000 g/mol. 
   
   
       10 . Dialdimine according to  claim 1 , wherein the diamine DA is an aliphatic diamine containing ether groups. 
   
   
       11 . Process for the preparation of a dialdimine of the formula (I) according to  claim 1 , comprising the step of reacting a diisocyanate DI with a dialdimine of the formula (IV), in the presence of water, 
     
       
         
         
             
             
         
       
       the diisocyanate DI and the dialdimine of the formula (IV) being reacted in the molar ratio of 
       [diisocyanate DI]/[dialdimine of the formula (IV)] of <1, and 
       the amount of water being chosen so that the molar ratio 
       [water]/[diisocyanate DI] is ≧2. 
     
   
   
       12 . Aldimine-containing emulsion comprising
 a) at least one dialdimine of the formula (I) according to  claim 1 ;   b) water; and   c) optionally at least one surfactant.   
   
   
       13 . Aldimine-containing emulsion according to  claim 12 , wherein the emulsion is free of organic VOC solvents. 
   
   
       14 . (canceled) 
   
   
       15 . Two-component composition consisting of two components C1 and C2,
 the component C1 containing at least one polymer having isocyanate groups;   and   the component C2 containing the dialdimine of the formula (I) according to  claim 1  or an aldimine-containing emulsion comprising   a) at least one dialdimine of the formula (I) according to  claim 1 ;   b) water; and   c) optionally at least one surfactant.   
   
   
       16 . Mixed or partly mixed two-component composition, wherein the component C1 and the component C2 of a two-component composition according to  claim 15  are mixed substantially homogeneously or inhomogeneously with one another, the mixing of the two components being effected via a static mixer or a dynamic mixer. 
   
   
       17 . (canceled) 
   
   
       18 . Process for the adhesive bonding of substrates S1 and S2, comprising:
 i) applying a two-component composition according to  claim 15  during the mixing or after the mixing of the two components C1 and C2 to a substrate S1; and   ii) bringing the applied composition into contact with a substrate S2;   or   i′) applying a two-component composition according to  claim 15  during the mixing or after the mixing of the two components C1 and C2 to a substrate S1;   ii′) applying a two-component composition according to  claim 15  during the mixing or after the mixing of the two components C1 and C2 to a substrate S2; and   iii′) bringing the composition applied to substrate S1 into contact with the composition applied to substrate S2;   the substrates S1 and S2 being identical or different from another.   
   
   
       19 . Process for sealing, comprising:
 i″) applying a two-component composition according to  claim 15  during the mixing or after the mixing of the two components C1 and C2 between a substrate S1 and a substrate S2;   the substrates S1 and S2 being identical or different from one another.   
   
   
       20 . Process for the production of a coating comprising:
 i′″) applying a two-component composition according to  claim 15  during the mixing or after the mixing of the two components C1 and C2 to a substrate S1.   
   
   
       21 . Process according to  claim 18 , wherein the mixing of the two components C1 and C2 is effected substantially homogeneously. 
   
   
       22 . Process according to  claim 18 , wherein the mixing of the two components C1 and C2 is effected substantially inhomogeneously. 
   
   
       23 . Process according to  claim 18 , wherein the substrate S1 and/or S2 is selected from the group consisting of concrete, cement, mortar, baked brick, brick, gypsum, natural stone, asphalt, metal, metal alloy, wood, ceramic, glass, plastic, powder coating, paint and finish. 
   
   
       24 . Article that is adhesively bonded, sealed or coated by a process according to  claim 18 . 
   
   
       25 . Article according to  claim 24 , wherein the article is a building, a structure of building construction or civil engineering, industrially produced goods or consumer goods, a household appliance, a means of transport, or an add-on part of a vehicle.