Preparation and use of 3, (4)-substituted pyrrolidines as catalysts for the polyisocyanate polyaddition process

A process or preparing 3,(4)-substituted pyrrolidine catalysts of the formula ##STR16## wherein R.sub.1 denotes hydrogen, a C.sub.1 -C.sub.12 -alkyl group, or an optionally alkyl-substituted C.sub.3 -C.sub.7 -cycloalkyl, aryl, or aralkyl group (with the proviso that each R.sub.1 may contain N or O atoms);

• or R.sub.1 denotes (i) together with R.sub.4 an optionally substituted C.sub.1 -C.sub.5 -alkylene group or (ii) a C.sub.1 -C.sub.6 -alkylene group connecting two pyrrolidine through the two ring nitrogen atoms;
• R.sub.2 and R.sub.3 independently denote hydroen, a C.sub.1 -C.sub.12 -alkyl group or an optionally alkyl-substituted cycloalkyl, aryl, or arylalkyl group;
• or R.sub.2 and R.sub.3 together denote an optionally alkyl-substituted C.sub.1 -C.sub.9 -alkylene group;
• R.sub.4 denotes hydrogen, a C.sub.1 -C.sub.12 -alkyl group, or an optionally alkyl-substituted C.sub.3 -C.sub.7 -cycloalkyl, aryl, or arylalkyl group;
• or R.sub.4 together with R.sub.1 denote an optionally substituted C.sub.1 -C.sub.5 -alkylene group;
• R.sub.5 and R.sub.6 independently denote hydrogen, a C.sub.1 -C.sub.12 -alkyl group or an optionally alkyl-substituted cycloalkyl, aryl, or arylalkyl group;
• or R.sub.5 and R.sub.6 together denote a group having the structure ##STR17## X.sub.4 and X.sub.5 independently denote hydrogen, carboxylic acid groups or ester or amide derivatives thereof, nitrile, or NO.sub.2 ;
• and
• Y.sub.1 denotes hydrogen, a carboxylic acid ester or amide derivative, or nitrile;
• comprising reacting, at an elevated temperature in an inert solvent, optionally with azeotropic removal of water,
• (a) an .alpha.-aminocarboxylic acid derivative of the formula
• R.sub.1 NH--CHR.sub.4 --Z
• wherein
• R.sub.2 denotes hydrogen, a C.sub.1 -C.sub.12 -alkyl group, or an optionally alkyl-substituted C.sub.3 -C.sub.7 -cycloalkyl, aryl, or an aralkyl group (with the proviso that each R.sub.1 may contain N or O atoms);
• or R.sub.1 denotes (i) together with R.sub.4 an optionally substituted C.sub.1 -C.sub.5 -alkylene group or (ii) a C.sub.1 -C.sub.6 -alkylene group connecting two .alpha.-aminocarboxylic acid derivatives through the .alpha.-amino nitrogen atom;
• R.sub.4 is defined as above;
• and
• Z denotes a carboxylic acid group or an ester or amide derivative thereof, or nitrile;
• with
• (b) a ketone or aldehyde of the formula
• R.sub.2 R.sub.3 C.dbd.O
• wherein R.sub.2 and R.sub.3 are defined as above;
• and
• (c) an activated olefin of the formula
• X.sub.4 R.sub.10 C.dbd.CR.sub.11 X.sub.5
• wherein
• X.sub.4 and X.sub.5 are defined as above;
• and
• R.sub.10 and R.sub.11 independently denote hydrogen, a C.sub.1 -C.sub.12 -alkyl group or an optionally alkyl-substituted cycloalkyl, aryl, or arylalkyl group;
• or R.sub.10 and R.sub.11 together form a third bond when R.sub.5 and R.sub.6 of the 3(4)-substituted pyrrolidine catalyst together denote a group having the formula ##STR18## with the proviso that the ketone or aldehyde is added continuously or in portions at the rate at which the reaction progresses.