Beta-hydroxyalkylamides, method for their production and use thereof

A method for the discontinuous preparation of an N,N,N′,N′-tetrakis(2-hydroxyethyl)cyclohexyl-1,4-diamide according to formula XIIA:

• the method comprising reacting dimethyl 1,4-cyclohexyldicarboxylate and diethanolamine in a solvent in an extruder, intensive compounder, intensive mixer or static mixer, wherein the N,N,N′,N′-tetrakis(2-hydroxyethyl)cyclohexyl-1,4-diamide has the following parameters:
• a trans content on the cyclohexyl ring of greater than or equal to 70 mol %, based on the total amount of all of the isomers of N,N,N′,N′-tetrakis(2-hydroxyethyl)cyclohexyl-1,4-diamide;
• two endothermic peaks according to DSC analysis (differential scanning calorimetry), where peak 1 is situated in the region of 140-170° C., with a maximum of 155-165° C., and peak 2 is situated in the region of 170-210° C., with a maximum of 175-207° C.;
• a ratio of the enthalpies of endothermic peak 1 to endothermic peak 2 is 1:1 to 1:5;
• and
• an XRPD spectrum of the powder sample in an x-ray diffractometer, measured with Cu Kα radiation (1.541 Å) has the following peaks:
• Degrees 2theta ±
• Peak #
• 0.2 degree 2theta
• d (Å)
• 1
• 14.90
• 5.94
• 2
• 16.70
• 5.31
• 3
• 17.40
• 5.09
• 4
• 21.20
• 4.19
• 5
• 21.60
• 4.11
• 6
• 26.00
• 3.43

A method for the discontinuous preparation of an N,N,N′,N′-tetrakis(2-hydroxyethyl)cyclohexyl-1,4-diamide according to formula XIIA:

• the method comprising reacting dimethyl 1,4-cyclohexyldicarboxylate and diethanolamine in closed apparatus under pressure at temperatures from 60 to 140° C. without addition of solvents, wherein the N,N,N′,N′-tetrakis(2-hydroxyethyl)cyclohexyl-1,4-diamide has the following parameters:
• a trans content on the cyclohexyl ring of greater than or equal to 70 mol %, based on the total amount of all of the isomers of N,N,N′,N′-tetrakis(2-hydroxyethyl)cyclohexyl-1,4-diamide that are present;
• two endothermic peaks according to DSC analysis (differential scanning calorimetry), where peak 1 is situated in the region of 140-170° C., with a maximum of 155-165° C., and peak 2 is situated in the region of 170-210° C., with a maximum of 175-207° C.;
• a ratio of the enthalpies of endothermic peak 1 to endothermic peak 2 is 1:1 to 1:5;
• and
• an XRPD spectrum of the powder sample in an x-ray diffractometer, measured with Cu Kα radiation (1.541 Å) has the following peaks:
• Degrees 2theta ±
• Peak #
• 0.2 degree 2theta
• d (Å)
• 1
• 14.90
• 5.94
• 2
• 16.70
• 5.31
• 3
• 17.40
• 5.09
• 4
• 21.20
• 4.19
• 5
• 21.60
• 4.11
• 6
• 26.00
• 3.43

A β-hydroxyalkylamide, comprising two or three or four β-hydroxyalkylamide groups per molecule of the formula I:

• wherein:
• R1 and R2 independently of one another are identical or different radicals selected from the group consisting of an alkyl radical, a cycloalkyl radical, an aryl radical, an aralkyl radical and an alkenyl radical having 1-24 carbon atoms, such that the radicals optionally comprise a heteroatom, functional group, or both, R1 is optionally a hydrogen, and R2 is optionally represented by the formula:
• A is represented by A1:
• wherein radicals R3 independently of one another are identical or different radicals selected from the group consisting of hydrogen, an alkyl radical, a cycloalkyl radical, an aryl radical, an aralkyl radical, and an alkenyl radical having 1-24 carbon atoms, such that the radicals optionally comprise a heteroatom, a functional group, or both, and two or more substituents R3 are optionally linked with one another to form rings;
• wherein the β-hydroxyalkylamide is present in solid form below 150° C.;
• wherein the β-hydroxyalkylamide has a trans content of greater than or equal to 70 mol % based on the total amount of all of the isomers of the β-hydroxyalkylamide;
• two endothermic peaks according to DSC analysis (differential scanning calorimetry), where peak 1 is situated in the region of 140-170° C., with a maximum of 155-165° C., and peak 2 is situated in the region of 170-210° C., with a maximum of 175-207° C.;
• a ratio of the enthalpies of endothermic peak 1 to endothermic peak 2 is 1:1 to 1:5;
• and
• a XRPD spectrum of the powder sample in an x-ray diffractometer, measured with Cu Kα radiation (1.541 Å) has the following peaks:
• Degrees 2theta ±
• Peak #
• 0.2 degree 2theta
• d (Å)
• 1
• 14.90
• 5.94
• 2
• 16.70
• 5.31
• 3
• 17.40
• 5.09
• 4
• 21.20
• 4.19
• 5
• 21.60
• 4.11
• 6
• 26.00
• 3.43.