N-(3-Hydroxyaryl-propyl)-imides

Abstract

The new N-[3-(3-hydroxyaryl)-2-hydroxypropyl]-imides may be prepared by reacting 3-(3-hydroxyaryl)-propenoxides with cyclic imides. These hydroxy compounds as well as their esters with carboxylic acids are highly effective in the stabilization of polymers, preferably of polyolefins, against thermal-oxydative attack. The compounds themselves exhibit a good stability against discoloration by radiation or gas fading.

What .[.we.]. .Iadd.I .Iaddend.claim is: .[.1. A compound of the formula ##STR33## wherein R is ##STR34## R 1  is an alkyl group of 1 to 8 carbon atoms, a cycloalkyl group of 6 to 8 carbon atoms, benzyl, α-methylbenzyl or α,α-dimethylbenzyl, R 2  is hydrogen, an alkyl group of 1 to 8 carbon atoms, a cycloalkyl group of 6 to 8 carbon atoms, benzyl, α-methylbenzyl, or α,α-dimethylbenzyl, R 3  is hydrogen or a methyl group, R 4  is hydrogen or a ##STR35## group, R 5  is an alkyl group of 1 to 17 carbon atoms, a cyclohexyl group, a phenyl group, a phenyl group substituted by halogen, alkoxy of 1-18 carbon atoms, hydroxyl, alkyl of 1-12 carbon atoms or alkyl of 1-4 carbon atoms and hydroxyl groups, benzyl, phenethyl, phenylpropyl; benzyl, phenethyl or phenylpropyl substituted by hydroxyl groups in the phenyl radical; benzyl, phenethyl or phenylpropyl substituted by alkyl groups of 1-4 carbon atoms in the phenyl radical; or benzyl, phenethyl or phenylpropyl substituted by alkyl of 1-4 carbon atoms and hydroxyl groups 
     
        in the phenyl radical..]. .[.2.  A compound according to claim 1, wherein R 1  and R 2  independently of one another are an alkyl group of 1 to 8 carbon atoms, R 3  is hydrogen, R 4  is hydrogen or a ##STR36## group, R 5  is an alkyl group of 1 to 17 carbon atoms, a cyclohexyl group, a phenyl group, a phenyl group substituted by halogen, hydroxyl groups, alkyl groups of 1 to 4 carbon atoms or alkoxy groups of 1 to 18 carbon atoms, or a benzyl or phenethyl group substituted in a phenyl radical by one or two alkyl groups of 1 to 4 carbon atoms, a hydroxyl group or one or two alkyl groups of 1 to 4 carbon atoms and a hydroxyl 
     
     
        group..]. .[.3.  A compound according to claim 1, wherein R 1  and R 2  independently of one another are an alkyl group of 1 to 4 carbon atoms, R 3  is hydrogen, R 4  is hydrogen or a ##STR37## group, and R 5  is an alkyl group of 1 to 17 carbon atoms or a ##STR38## 
     
     
        group..]. .[.4.  A compound according to claim 1, wherein R 1  and R 2  independently of one another are an alkyl group of 1 to 4 carbon 
     
     
        atoms and R 3  and R 4  are hydrogen..]. 5. The compound .[.according to claim 1.]. of the formula ##STR39## wherein R represents the ##STR40## 
     
     
        6. The compound .[.according to claim 1.]. of the formula ##STR41## wherein R' represents the ##STR42## 
     
     
         .Iadd.7.  A compound of the formula .Iaddend. ##STR43## .Iadd. wherein each R is .Iaddend. ##STR44## .Iadd.in which each of R 1  and R 2  is alkyl of 1 to 8 carbon atoms and R 4  is hydrogen or .Iaddend. ##STR45## .Iadd.in which R 5  is alkyl of 1 to 17 carbon atoms or 
     
     
        2-(3,5-di-t-butyl-4-hydroxyphenyl)ethyl. .Iaddend. .Iadd. 8.  A compound according to claim 7 wherein R 1  is methyl, isopropyl or t-butyl;   R 2  is isopropyl or t-butyl; and   R 4  is hydrogen, acetyl or 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionyl. .Iaddend.