Beta-hydroxyalkylamides, a method for production of same and use of same
AssigneeEvonik Degussa GmbH
InventorsWerner Grenda, Emmanouil Spyrou
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Abstract
The invention relates to new β-hydroxyalkylamides, to a method for production of same and to the use of same.
Claims24
β-Hydroxyalkylamides having two or three or four β-hydroxyalkylamide groups per molecule of formula I
- where
- R1, R2:
- 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 R1 may also be hydrogen,
- and wherein R2 may also be
- where R3:
- 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 R3 substituents may be linked to one another to form rings;
- wherein the 3-hydroxyalkylamides exist in solid form below 150° C.
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.
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
- R1 denotes hydrogen, methyl, ethyl, propyl,
- R2 denotes methyl;
- where R1 denotes hydrogen, methyl, ethyl, propyl, either simultaneously or independently of one another.
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.
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.
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 R4 denotes methyl, ethyl, propyl, butyl simultaneously or independently of one another.
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.
β-Hydroxyalkylamides according to at least one of the preceding claims,
- characterized in that
- the β-hydroxyalkylamides have the following formulas:
- where
- R2:
- methyl,
- or
- where R1A denotes hydrogen and R1B denotes methyl, ethyl, propyl,
- or
- where R1A denotes methyl, ethyl, propyl and R1B 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.
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 %.
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 %.
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.
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
- R1, R2:
- 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 R1 may also be hydrogen,
- and wherein R2 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.
The use of β-hydroxyalkylamides having two or three or four β-hydroxyalkylamide groups per molecule of formula I
- where
- R1, R2:
- 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 R1 may also be hydrogen,
- and wherein R2 may also be
- where R3:
- 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 R3 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.
The use of β-hydroxyalkylamides having two or three or four β-hydroxyalkylamide groups per molecule of formula I
- where
- R1, R2:
- 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 R1 may also be hydrogen,
- and wherein R2 may also be
- where R3:
- 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 R3 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.
Dependencies are inferred from the claim text.