CPC A61K 6/893 (2020.01) [A61K 6/30 (2020.01); A61K 6/62 (2020.01); A61K 6/889 (2020.01); C08L 35/02 (2013.01)] | 3 Claims |
1. Process for preparing a polymerizable compound having at least one optionally derivatized β-hydroxy urethane unit, which are represented by the following formula IIId-IIIg:
![]() wherein
R represents a divalent unsubstituted or substituted C1-C18 alkylene group, an unsubstituted or substituted C3-C8 cycloalkylene group, an unsubstituted or substituted aralkylene group, an unsubstituted or substituted C5-C18 arylene group or unsubstituted or substituted C3-C18 heteroarylene group;
R1 is an unsubstituted or substituted C2-10 alkyl group, an unsubstituted or substituted C3-C6 cycloalkyl group, an unsubstituted or substituted C1-C8 cycloalkylalkylene, an unsubstituted or substituted C5-C18 aryl group, an unsubstituted or substituted C7-C24 aralkyl group, wherein each substituted group is substituted by one or more of a C1-4 alkyl group, a C1-4 alkoxy group, a hydroxyl group, an aryl group or an aryloxy group;
R2, R3 and R4 are independent from each other, and represent a hydrogen or a C1-4 alkyl group;
Z is a divalent aliphatic C2-10 group, a divalent cycloaliphatic C3-C6 group or an aralkylene group having 7 to 24 carbon atoms, wherein each group optionally contain oxygen atoms and which is optionally substituted by C1-4 alkyl group;
R5 is a mono-valent aliphatic C1-10 group, cycloaliphatic C3-C6 group or an aralkylene group having 7 to 24 carbon atoms;
R6 is a hydrogen atom, a C1-6 alkyl group, a C3-10 cycloalkyl group, a C7-C12 aralkyl group, or an (meth) acryl group; wherein each group is optionally substituted by one or more of a C1-4 alkyl group, a C1-4 alkoxy group, or a hydroxyl group;
R7 is
![]() wherein R8 is a hydrogen atom, or a linear C1-3 or branched C3-5 alkyl group substituted with a COOH group;
R9 is a hydrogen atom, —COOH group, or a linear C1-3 or branched C3-5 alkyl group substituted with a COOH group;
A is independently same or different and is a hydrogen atom or R7;
X1 is an oxygen atom or a nitrogen atom substituted by R6;
n is an integer of from 1 to 5;
said process comprising the steps of:
(a) reacting at least one component A having at least one cyclic carbonate group with at least one component B having at least one of primary amine functional group and secondary amine functional group to form an intermediate compound having at least one β-hydroxy urethane unit and residual —NH or —OH group; and
(b) reacting the intermediate compound having at least one β-hydroxy urethane unit and residual —NH or —OH group with at least one unsaturated mono- or poly-carboxylic acid to form a polymerizable compound having at least one derivatized β-hydroxy urethane unit,
wherein
the at least one component A having at least one cyclic carbonate group is a compound of Formula I:
![]() wherein
R1 represents a hydrogen, an m-valent C1-22 hydrocarbon group, which group optionally includes 1 to 12 oxygen or sulfur atoms, and which is optionally substituted by C1-4 alkyl group or a (meth)acrylate group;
R2, R3 and R4 are independent from each other, and represent a hydrogen or a C1-4 alkyl group;
W is an oxygen atom, —O—C═O— or a direct bond;
Q is a direct bond or a straight or branched chain alkylene having 1 to 4 carbons;
Y is a direct bond, an unsubstituted or substituted C1-C18 alkylene group, an unsubstituted or substituted C3-C8 cycloalkylene group, an unsubstituted or substituted aralkylene group, an unsubstituted or substituted C5-C18 arylene group or an unsubstituted or substituted C3-C18 heteroarylene group; wherein each unsubstituted or substituted group optionally includes at least one of 1-6 oxygen atoms, nitrogen atoms or sulphur atoms; wherein each substituted groups is substituted by C1-4 alkyl group;
m is an integer of from 1 to 6; and
wherein the at least one component B having at least one of primary amine functional group and secondary amine functional group is a compound of Formula II:
![]() wherein
R5 is a (r+1)-valent aliphatic C2-10 group, cycloaliphatic C3-C6 group or an aralkylene group having 7 to 24 carbon atoms, wherein each group optionally contains oxygen or sulfur atoms and which is optionally substituted by C1-4 alkyl groups;
R6 is a hydrogen atom, a C1-6 alkyl group, a C3-10 cycloalkyl group, a C7-C12 aralkyl group, or an (meth) acryl group; wherein each group is optionally substituted by one or more of a C1-4 alkyl group, a C1-4 alkoxy group, or a hydroxyl group;
L1 and L2 are independently a same or different straight or branched chain alkylene having from 1 to 4 carbons;
X1 is a direct bond, an oxygen atom or a nitrogen atom substituted by R6;
X2 is an oxygen atom;
p and q are integer of from 0 to 4; and
r is an integer of from 1 to 6.
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