Polymerizable anthracene derivatives for labeling emulsion copolymers

We describe the synthesis of three anthracene-methacrylate monomers [9-meth acryloxymethyl-10-methyl anthracene (4), 9-methacryloxyethyloxymethyl-10-me thyl anthracene (5), and 9-methacryloxy-10-methyl anthracene (6)] as well a s their emulsion copolymers containing butylacrylate. When films prepared f rom latex dispersions containing 4 or 5 were heated, the antkracene (An) gr oup was cleaved from the polymer at temperatures above 120 degreesC. Lower temperatures induced this reaction when strong acids were present. In 4 and 5, the polymerizable group is connected to the An ring via a 9-CH2O- linka ge. The cleavage reaction requires more stringent conditions when the conne ction involves a benzylic ether (5) instead of a benzylic ester. Polymers p repared from 6, with an An-O- bond, were stable for 1 h at 150 degreesC in the presence of 0.5 wt % p-toluene sulfonic acid. (C) 2001 John Wiley & Son s, Inc.