Specific mixtures of N,N-bis(2-hydroxyalkyl)-4-toluidine derivatives, their preparation and a method of using such specific mixtures

Abstract

A process is provided for preparing new mixtures of N,N-bis(2-hydroxyalkyl)-4-toluidine derivatives which can be used as polymerization accelerators.

1 . A process for preparing a mixture of two or more different compounds of the general formula (I)  
     
       
         
         
             
             
         
       
     
     in which 
 n and m independently of one another are each an integer in the range from 0 to 11, but the sum of n and m is at least 1, and  
 R 1  radicals are identical or different and can be hydrogen or methyl, although two radicals R 1  located on directly adjacent carbon atoms are not simultaneously methyl,  
 by reacting 4-toluidine, containing less than 0.2% by weight of 3-toluidine, based on 4-toluidine, with at least 2 mol of an alkylene oxide of the formula (II) per mole of 4-toluidine  
                     
 where R 1  possesses the definition specified for the formula (I).  
 
   
   
       2 . The process according to  claim 1 , wherein not only compounds of the general formula (I) in which n and m are identical in the respective molecule but also compounds of the general formula (I) in which n and m possess different values in the respective molecule are obtained.  
   
   
       3 . The process according to  claim 1 , wherein 2.2 to 5 mol, preferably 2.3 to 4 mol, more preferably 2.3 to 3.5 mol and in particular 2.5 to 2.6 mol of alkylene oxide of the general formula (II) are used per mole of 4-toluidine.  
   
   
       4 . The process according to  claim 1 , wherein the reaction is carried out at a temperature in the range from 100 to 170° C., preferably in the range from 110 to 160° C., more preferably in the range from 120 to 150° C.  
   
   
       5 . The process according to  claim 1 , wherein the reaction is carried out using basic catalysts, preferably NaOH, KOH or NaOCH 3 .  
   
   
       6 . The process according to  claim 1 , wherein a 4-toluidine is used which contains 0.05% to 0.19%, preferably 0.08% to 0.18%, in particular 0.08% to 0.15% and with particular preference 0.08%-0.12% by weight of 3-toluidine.  
   
   
       7 . A mixture of two or more different compounds of the general formula (I) obtainable by the process according to  claim 1 .  
   
   
       8 . A method of using the mixture according to  claim 7  comprising preparing a polymer, preferably a polyester, especially an unsaturated polyester, by a free-radical addition polymerization in the presence of the mixture according to  claim 7  as a polymerization accelerator or vulcanization accelerator.  
   
   
       9 . A polymeric product obtainable by free-radical addition polymerization in the presence of a mixture according to  claim 7  as polymerization accelerator or vulcanization accelerator.