Sugar-Functional Vinyl Addition Poly(norbornene)–Photopatternable Poly(norbornenyl gluconamide) Compositions Developed with Water

The norbornenyl gluconamide (NBGA) monomer can be polymerized by a number of palladium catalysts to give water-soluble, vinyl addition poly­(NBGA). Depending on the catalyst used, the reaction conditions, and the chain-transfer additives employed, high-molecular-weight polymers can be obtained. These polymers can be thermally cross-linked at ca. 190 °C or at ca. 150 °C when the difunctional glutaraldehyde is added. A photopatternable composition is formed by the addition of a water-soluble diazide when the poly­(NBGA) molecular weight is sufficiently high. After image-wise exposure, negative-tone patterns are revealed by water development. A detailed analysis of NBGA monomer structures by high-resolution nuclear magnetic resonance techniques including pure shift is reported showing that two diastereomers of each endo- and exo-isomer are formed from the reaction of norbornene methylamine and δ-gluconolactone.