Beta-hydroxyalkylamides, a method for production of same and use of same

Abstract

The invention relates to new β-hydroxyalkylamides, to a method for production of same and to the use of same.

1 . β-Hydroxyalkylamides having two or three or four β-hydroxyalkylamide groups per molecule of formula I 
       
         
           
           
               
               
           
         
         where 
         R 1 , R 2 : independently of one another denote the same or different radicals, selected from alkyl radicals, cycloalkyl radicals, aryl radicals, aralkyl radicals or alkenyl radicals having 1-24 carbon atoms, wherein the radicals may also contain heteroatoms and/or functional groups and wherein R 1  may also be hydrogen, 
         and wherein R 2  may also be 
       
       
         
           
           
               
               
           
         
         where R 3 : independently of one another denote the same or different radicals, selected from hydrogen, alkyl radicals, cycloalkyl radicals, aryl radicals, aralkyl radicals or alkenyl radicals having 1-24 carbon atoms, wherein the radicals may also contain heteroatoms and/or functional groups and wherein two or more R 3  substituents may be linked to one another to form rings; 
         wherein the 3-hydroxyalkylamides exist in solid form below 150° C. 
       
     
     
         2 . β-Hydroxyalkylamides according to  claim 1 ,
 characterized in that 
 as starting compounds there are used β-hydroxyalkylamines containing alkyl groups having at least 2 to 10 carbon atoms in the hydrocarbon skeleton, wherein the alkyl groups may be linear, branched or even cyclic, and wherein the alkyl groups may be substituted with hetero atoms, preferably oxygen and nitrogen, these alkyl groups may also contain functional groups, preferably carbonyl groups, carboxyl groups, amino groups, amide groups, urethane groups, and may have an additional alkyl radical on the nitrogen. 
 
     
     
         3 . β-Hydroxyalkylamides according to at least one of the preceding claims,
 characterized in that 
 they contain β-hydroxyalkylamides of N-alkyl-1,2-alkanolamines and/or of N,N-bis-2-hydroxyalkylamines and esters of cyclohexanedicarboxylic acids. 
 
     
     
         4 . β-Hydroxyalkylamides according to at least one of the preceding claims,
 characterized in that 
 there are used β-hydroxyalkylamines of formulas II and/or III as starting compounds 
 
       
         
           
           
               
               
           
         
         where 
         R 1  denotes hydrogen, methyl, ethyl, propyl, 
         R 2  denotes methyl; 
       
       
         
           
           
               
               
           
         
         where R 1  denotes hydrogen, methyl, ethyl, propyl, either simultaneously or independently of one another. 
       
     
     
         5 . β-Hydroxyalkylamides according to at least one of the preceding claims,
 characterized in that 
 the following compounds are used as starting materials for production of the β-hydroxyalkylamides: diethanolamine (DEA), diisopropanolamine (DIPA), di-sec-butanolamine, N-methylethanolamine, N-methyl-isopropanolamine. 
 
     
     
         6 . β-Hydroxyalkylamides according to at least one of the preceding claims,
 characterized in that 
 1,2 substituted, 1,3-substituted and 1,4-substituted cyclohexanedicarboxylic acid derivatives, especially cyclohexanedicarboxylic acid dialkyl esters, are used as starting compounds for substituents A for production of the p-hydroxyalkylamides. 
 
     
     
         7 . β-Hydroxyalkylamides according to at least one of the preceding claims, characterized in that
 for production of the β-hydroxyalkylamides, there are used compounds of formula IV 
 
       
         
           
           
               
               
           
         
       
       where R 4  denotes methyl, ethyl, propyl, butyl simultaneously or independently of one another. 
     
     
         8 . β-Hydroxyalkylamides according to at least one of the preceding claims,
 characterized in that 
 1,4-substituted cyclohexanedicarboxylic acid esters, preferably dimethyl-1,4-cyclohexyl dicarboxylate, are used as starting compounds. 
 
     
     
         9 . β-Hydroxyalkylamides according to at least one of the preceding claims,
 characterized in that 
 the β-hydroxyalkylamides have the following formulas: 
 
       
         
           
           
               
               
           
         
         where 
         R 2 : methyl, 
         or 
       
       
         
           
           
               
               
           
         
         where R 1A  denotes hydrogen and R 1B  denotes methyl, ethyl, propyl, 
         or 
         where R 1A  denotes methyl, ethyl, propyl and R 1B  denotes hydrogen; 
         and 
         A: 1,4-disubstituted cyclohexane ring of the formula 
       
       
         
           
           
               
               
           
         
         wherein the trans content of A is ≧70 mol %; 
         and wherein the β-hydroxyalkylamides exist in solid form below 150° C. 
       
     
     
         10 . β-Hydroxyalkylamides according to at least one of the preceding claims, comprising dialkyl-1,4-cyclohexyldicarboxylates, preferably dimethyl-1,4-cyclohexyldicarboxylate, having a trans content, relative to the position of the carboxyl groups on the cyclohexyl ring, of greater than or equal to 70 mol %, preferably greater than 80 mol % and particularly preferably greater than 85 mol %. 
     
     
         11 . β-Hydroxyalkylamides according to at least one of the preceding claims, comprising dimethyl-1,4-cyclohexyldicarboxylate and diethanolamine and having four β-hydroxyalkylamide groups per molecule according to formula XII, 
       
         
           
           
               
               
           
         
         with a trans content on the cyclohexyl ring of greater than or equal to 70 mol %, preferably greater than 80 mol % and particularly preferably greater than 85 mol %. 
       
     
     
         12 . β-Hydroxyalkylamides according to at least one of the preceding claims,
 characterized in that 
 the β-hydroxyalkylamides exist in solid form below 150° C., preferably below 170° C., particularly preferably below 180° C. 
 
     
     
         13 . A method for solvent-free and continuous production of 3-hydroxyalkylamides having at least two or three or four β-hydroxyalkylamide groups per molecule of formula I 
       
         
           
           
               
               
           
         
         where 
         R 1 , R 2 : independently of one another denote the same or different radicals, selected from hydrogen, alkyl radicals, cycloalkyl radicals, aryl radicals, aralkyl radicals or alkenyl radicals having 1-24 carbon atoms, wherein the radicals may also contain heteroatoms and/or functional groups and wherein R 1  may also be hydrogen, 
         and wherein R 2  may also be 
       
       
         
           
           
               
               
           
         
         A: 1,4-disubstituted cyclohexane ring of the formula 
       
       
         
           
           
               
               
           
         
         wherein the trans content of A is z 70 mol %; 
         and 
         wherein the β-hydroxyalkylamides (I) exist in solid form below 150° C., in an extruder, flow tube, intensive kneader, intensive mixer or static mixer. 
       
     
     
         14 . A method for solvent-free, continuous production of β-hydroxyalkylamides according to  claim 13  from dialkyl-1,4-cyclohexyl dicarboxylates, especially from dimethyl-1,4-cyclohexyl dicarboxylate, having a trans content on the cyclohexyl ring of greater than or equal to 70 mol %, preferably greater than 80 mol % and particularly preferably greater than 85 mol %, and existing in solid form below 150° C. 
     
     
         15 . A method according to  claim 13  or  14 ,
 characterized in that 
 the dialkyl-1,4-cyclohexyl dicarboxylates used have any desired trans content. 
 
     
     
         16 . A method according to  claims 13  to  15 , by intensive intermixing and short-time reaction with heat input at temperatures of >50° C., followed by isolation of the end product by cooling. 
     
     
         17 . A method according to  claims 13  to  16 ,
 characterized in that 
 the dwell time of the feed substances ranges from 3 seconds to 15 minutes. 
 
     
     
         18 . A method according to one of  claims 13  to  17 ,
 characterized in that 
 the reaction takes place in single-screw, twin-screw or multi-screw extruders, ring extruders or planetary rolling extruders, preferably in a twin-screw extruder. 
 
     
     
         19 . A method according to one of  claims 13  to  18 ,
 characterized in that 
 the temperature in the extruder, intensive kneader, intensive mixer or static mixer is 50 to 325° C. 
 
     
     
         20 . A method according to one of  claims 13  to  19 ,
 for production of the β-hydroxyalkylamide comprising dimethyl-1,4-cyclohexyldicarboxylate and diethanolamine having four β-hydroxyalkylamide groups per molecule, of formula XII, 
 
       
         
           
           
               
               
           
         
         with a trans content on the cyclohexyl ring of greater than or equal to 70 mol %, preferably greater than 80 mol % and particularly preferably greater than 85 mol %. 
       
     
     
         21 . The use of β-hydroxyalkylamides having two or three or four β-hydroxyalkylamide groups per molecule of formula I 
       
         
           
           
               
               
           
         
         where 
         R 1 , R 2 : independently of one another denote the same or different radicals, selected from alkyl radicals, cycloalkyl radicals, aryl radicals, aralkyl radicals or alkenyl radicals having 1-24 carbon atoms, wherein the radicals may also contain heteroatoms and/or functional groups and wherein R 1  may also be hydrogen, 
         and wherein R 2  may also be 
       
       
         
           
           
               
               
           
         
         where R 3 : independently of one another denote the same or different radicals, selected from hydrogen, alkyl radicals, cycloalkyl radicals, aryl radicals, aralkyl radicals or alkenyl radicals having 1-24 carbon atoms, wherein the radicals may also contain heteroatoms and/or functional groups and wherein two or more R 3  substituents may be linked to one another to form rings; 
         wherein the β-hydroxyalkylamides exist in solid form below 150° C.; 
         for the production of coatings having matte surfaces. 
       
     
     
         22 . The use of β-hydroxyalkylamides having two or three or four β-hydroxyalkylamide groups per molecule of formula I 
       
         
           
           
               
               
           
         
         where 
         R 1 , R 2 : independently of one another denote the same or different radicals, selected from alkyl radicals, cycloalkyl radicals, aryl radicals, aralkyl radicals or alkenyl radicals having 1-24 carbon atoms, wherein the radicals may also contain heteroatoms and/or functional groups and wherein R 1  may also be hydrogen, 
         and wherein R 2  may also be 
       
       
         
           
           
               
               
           
         
         where R 3 : independently of one another denote the same or different radicals, selected from hydrogen, alkyl radicals, cycloalkyl radicals, aryl radicals, aralkyl radicals or alkenyl radicals having 1-24 carbon atoms, wherein the radicals may also contain heteroatoms and/or functional groups and wherein two or more R 3  substituents may be linked to one another to form rings; 
         wherein the β-hydroxyalkylamides exist in solid form below 150° C.; 
         as cross-linking agents for carboxyl-group-containing polymers, preferably for carboxyl-group-containing polyesters. 
       
     
     
         23 . The use according to  claim 22  in powder lacquers, preferably in carboxyl-group-containing polyester powder lacquers. 
     
     
         24 . The use of the β-hydroxyalkylamides according to at least one of  claims 1  to  13  in powder lacquers, for production of matte coatings (<50 gloss units, measured as reflectometer values according to DIN 67530/ISO 2813 at an angle of incidence of 60°).