Production of (meth)acrylates of cyclic or open-chain N-hydroxyalkylated amides, used as (co)monomer in poly(meth)acrylates or in radiation cure, uses inorganic salt or enzyme as heterogeneous catalyst for esterification or ester exchange

摘要

Production of (meth)acrylates (I) of cyclic or open-chain N-hydroxyalkylated amides (II) involves esterification of (II) with (meth)acrylic acid or ester exchange with (meth)acrylic ester(s) in the presence of heterogeneous catalyst(s) selected from inorganic salts (III) and enzymes (IV). Production of (meth)acrylates (I) of cyclic or open-chain N-hydroxyalkylated amides (II) of formulae (IIA) and (IIB) respectively involves esterification of (II) with (meth)acrylic acid or ester exchange with (meth)acrylic ester(s) in the presence of heterogeneous catalyst(s) selected from inorganic salts (III) and enzymes (IV). Z 1oxygen (O), sulfur (S), (un)substituted phosphorus (P) or mono- or un-substituted nitrogen (N-R 3); R 1, R 32-20 C alkylene, 5-12 C cycloalkylene, 6-12 C arylene or a 2-20 C alkylene group with 1 or more O and/or S atoms, (un)substituted imino groups and/or cycloalkyl, -(CO)-, -O(CO)O-, -(NH)(CO)O-, -O(CO)(NH)-, -O(CO)- or -(CO)O- groups in the chain, where any of these groups may be substituted by R; R : aryl, alkyl, aryloxy, alkoxy, heteroatoms and/or heterocycles; or R 2-OH : -[X i] k-H; R 3, R 4, R 5H, 1-18 C alkyl, 2-18 C alkyl, optionally with O and/or S atoms and/or (un)substituted imino groups in the chain, 2-18 C alkenyl, 6-12 C aryl, 5-12 C cycloalkyl or a 5-7-membered heterocycle containing O, N and/or S atom(s), where any of these groups may be substituted R; or R 3R 6a group forming 5-12-membered ring; k : 1-50; X i-CH 2-CH 2-O-, -CH 2-CH 2-N(H)-, -CH 2-CH 2-CH 2-N(H)-, -CH 2-CH(NH 2)-, -CH 2-CH(NHCHO)-, -CH 2-CH(CH 3)-O-, -CH(CH 3)-CH 2-O-, -CH 2-C(CH 3) 2-O-, -C(CH 3) 2-CH 2-O-, -CH 2-CH 2-CH 2-O-, -CH 2-CH 2-CH 2-CH 2-O-, -CH 2-CHVin-O-, -CHVin-CH 2-O-, -CH 2-CHPh-O- or -CHPh-CH 2-O-; Ph : phenyl; Vin : vinyl; i : 1-k; and R 5unsubstituted 1-18 C alkyl, 6-12 C aryl or 5-12 C cycloalkyl if Z 1 = O. [Image].