Evaluation of hindered amine light stabilisers and their N-chlorinated derivatives as antibacterial and antifungal additives for thermoset surface coatings

Abstract

N-Halogenated amines or ‘halamines’ have attracted recent attention as potential biocides for materials and surface coatings application. Facile N-chlorination of the hindered amine light stabiliser (HALS) Tinuvin®770, bis-(2,2,6,6-tetramethyl-4-piperidinyl) sebacate, was achieved by reaction with sodium dichloroisocyanurate. The chlorinated product was incorporated into a polyester-based paint formulated for coil coating, applied to test panels and subjected to high temperature curing conditions characteristic of the coil coating process (55 s at 262 °C). Rapid detection of N-chlorinated Tinuvin®770 in the cured coating was confirmed, using liquid extraction surface analysis-mass spectrometry, by the characteristic fragmentation patterns of the halamines observed upon collision-induced dissociation. Antimicrobial activity of the coating was determined by testing against the bacterium Pseudomonas aeruginosa and the fungus Cladosporium sp., two organisms that are known to colonise both internal and external surfaces in building and cladding applications. The activity of HALS and halamine containing coatings were compared against a commercial product containing an antimicrobial additive as well as control surfaces without additives. Significant activity against the bacterium, but not against the fungus was demonstrated for the parent HALS and halamine containing coatings. The possibility of regeneration of the halamines was also tested and confirmed by mass spectrometry, post-chlorination of samples showed no significant differences in activity between corresponding pairs of samples.