Process for the synthesis of polyalkylphenol antioxidants

A method of synthesizing an antioxidant polymer, comprising the steps of

• a) partially etherifying a phenol derivative represented by the following structural formula:
• wherein:
• at least one ring carbon atom substituted with an —OH group is adjacent to one unsubstituted ring carbon atom;
• X is —O—, —NH— or —S—;
• each R10 is independently an optionally substituted C1-C10 alkyl group, an optionally substituted aryl group, and optionally substituted alkoxy group, an optionally substituted carbonyl group, an optionally substituted alkoxycarbonyl group, an optionally substituted aryloxycarbonyl group, —OH, —SH or —NH2;
• or two R10 groups on adjacent carbon atoms join together to form an optionally substituted aromatic ring or an optionally substituted carbocyclic or heterocyclic non-aromatic ring;
• and
• q is an integer from 0 to 2;
• by contacting the phenol derivative with an alkyl halide, alcohol or olefin to produce an alkoxy phenol derivative represented by the following structural formula:
• R is an optionally substituted C1-C10 alkyl group;
• b) polymerizing the alkoxy phenol derivative to produce an alkoxy phenol polymer comprising at least one repeat unit selected from:
• n is an integer greater than or equal to 2;
• and
• c) thermally rearranging the alkyl portion of the alkoxy group of the polymer repeat units to the adjacent ring carbon atom to give a polymeric alkyl phenol derivative antioxidant comprising at least one repeat unit selected from: