Synthesis and antibiofouling properties of novel crosslinkable terpolymers containing semifluoroalkyl substituted aromatic side chains

Abstract

Synthesis, contact angle analysis, surface properties and biofouling characteristics of novel crosslinkable terpolymers with semifluoroalkyl substituted aromatic side chains have been described. These polymers are targeted for use as coatings to prevent marine biofouling. The marine antifouling properties of these materials were evaluated by laboratory assays employing the fouling diatom Nitzschia and ubiquitous Staphylococcus aureusi. Results indicated that the experimental coatings exhibited better antibiofouling performance than that of a standard Poly(dimethyl siloxane) (PDMS) coating. POLYM. ENG. SCI.,

Synthesis and antibiofouling properties of crosslinkable copolymers grafted with fluorinated aromatic side chains

“…NMR spectra were recorded at ambient temperature on a Bruker AV400 spectrometer at 400.0 and 377.0 MHz for 1 H and 19 F nuclei, respectively. Tetramethylsilane (TMS) was applied as the internal chemical shi reference for 1 H NMR spectra and CFCl 3 as an external standard for 19 F NMR spectra, downeld shis are designated as positive. Fourier transform infrared (FT-IR) spectra were recorded on a FT-IR spectrometer (Avatar 380) using KBr crystals in the infrared region of 4000-400 cm À1 .…”

“…18 (2.16 g, 67% yield), 1 H NMR (400 MHz, CDCl 3 ) d (ppm): 6.66 (dd, J ¼ 18.0, 11.9 Hz, 1H), 6.08 (d, J ¼ 18.0 Hz, 1H), 5.69 (d, J ¼ 11.9 Hz, 1H), 4.53 (t, J ¼ 6.7 Hz, 2H), 2.79-2.60 (m, 2H). 19 F NMR (377 MHz, CDCl 3 ) d (ppm): À80.8 (t, J ¼ 10.3 Hz, 3F), À113.4 (dt, J ¼ 33.5, 18.5 Hz, 2F), À121.9 (s, 2F), À122.9 (s, 2F), À123.5 (s, 2F), À126.0 to À126.4 (m, 2F), À144.4 (dd, J ¼ 22.1, 10.0 Hz, 2F), À158.1 (dd, J ¼ 21. 8, 9.7 19 F NMR (377 MHz, CDCl 3 ) d (ppm): À80.2 to À83.3 (m, 13F), À130.0 to À130.6 (m, 2F), À134.2 to À136.2 (m, 1F), À144.0 to À144.6 (m, 2F), À145.1 to À145.9 (m, 1F), À157.7 to À160.4 (m, 2F General procedure for copolymerization.…”

“…19 F NMR (377 MHz, CDCl 3 ) d (ppm): À80.8 (t, J ¼ 10.3 Hz, 3F), À113.4 (dt, J ¼ 33.5, 18.5 Hz, 2F), À121.9 (s, 2F), À122.9 (s, 2F), À123.5 (s, 2F), À126.0 to À126.4 (m, 2F), À144.4 (dd, J ¼ 22.1, 10.0 Hz, 2F), À158.1 (dd, J ¼ 21. 8, 9.7 19 F NMR (377 MHz, CDCl 3 ) d (ppm): À80.2 to À83.3 (m, 13F), À130.0 to À130.6 (m, 2F), À134.2 to À136.2 (m, 1F), À144.0 to À144.6 (m, 2F), À145.1 to À145.9 (m, 1F), À157.7 to À160.4 (m, 2F General procedure for copolymerization. To a 25 mL threenecked round-bottomed ask equipped with a reux condenser were added MMA (1.0 g, 10.0 mmol), GMA (1.0 g, 7.7 mmol), 1a (1.0 g, 1.9 mmol, 33 wt%), AIBN (0.03 g, 0.2 mmol) and THF (10 mL) under a nitrogen atmosphere.…”

“…The product was dried in a vacuum oven overnight to afford polymer 2a as a white solid (2.52 g, 84% yield). 19 Polymer 2b-2e were prepared following a similar procedure to that used for 2a, but the amount of MMA was kept constant, and the mass fraction of 1a was controlled as 20 wt%, 10 wt%, 5 wt%, 0 wt% to get polymer 2b (83% yield), 2c (83% yield), 2d (83% yield), 2e (87% yield), respectively. Polymers 2a-2e were all white solids.…”

“…The residue was puried by ash chromatography (petroleum ether) to give compound 1c (0.842 g, 90% yield) as a yellowish solid. 1 19 F NMR (377 MHz, CDCl 3 ) d (ppm): À80.7 (t, J ¼ 9.9 Hz, 3F), À113.2 to À113.4 (m, 2F), À121 (s, 2F), À122.8 (s, 2F), À123.5 (s, 2F), À126.0 to À126.2 (m, 2F). IR (KBr, cm À1 ): 2969, 2928, 1607, 1514, 1405, 1234, 1177, 1137.…”