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(12) United States Patent (10) Patent No.: US 9,580,608 B1 Denton Et Al

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(12) United States Patent (10) Patent No.: US 9,580,608 B1 Denton Et Al USOO958.0608B1 (12) United States Patent (10) Patent No.: US 9,580,608 B1 Denton et al. (45) Date of Patent: Feb. 28, 2017 (54) SWITCHABLE ANTIFOULING COATINGS Eshet, I. et al., “Chemical and Physical Factors in Design of AND USES THEREOF Antibiofouling Polymer Coatings.” Biomacromolecules (2011) pp. 2681-2685, 12. Graham, M.V. et al., “Development of antifouling surfaces to reduce (71) Applicant: Sandia Corporation, Albuququerque, bacterial attachment.” Soft Matter (2013) pp. 6235-6244, 9. NM (US) Johnson, R.S. et al., “Thermally Induced Failure of Polymer Dielec trics.” Adv. Mater. (2010) pp. 1750-1753, 22. (72) Inventors: Michele L. Baca Denton, Bosque, NM Johnson, R.S. et al., “Photopatterning poly(p-phenylenevinylene) from Xanthate precursor polymers,” Chem. Commun. (2011) pp. (US); Shawn M. Dirk, Albuquerque, 3936-3938, 47. NM (US); Ross Stefan Johnson, Johnson, R.S. et al., “Photolithographic patterning of alkoxy sub Wilmington, DE (US) stituted poly(p-phenylenevinylene)s from Xanthate precursors,” J. Mater. Chem. C (2013) pp. 1428-1433, 1. (73) Assignee: Sandia Corporation, Albuquerque, NM Johnson, R.S. et al., “Thermally-Activated Pentanol Delivery from Precursor Poly(p-phenylenevinylene)s for MEMS Lubrication.” (US) Macromol. Rapid Commun. (2012) pp. 1346-1350, 33. Kanazawa, A. et al., “Novel Polycationic Biocides: Synthesis and (*) Notice: Subject to any disclaimer, the term of this Antibacterial Activity of Polymeric Phosphonium Salts.” J. Polym. patent is extended or adjusted under 35 Sci. Part A: Polym. Chem. (1993) pp. 335-343, 31. U.S.C. 154(b) by 21 days. Kanazawa, A. et al., “Antibacterial Activity of Polymeric Sulfonium Salts.” J. Polym. Sci. Part A: Polym. Chem. (1993) pp. 2873-2876, 31. (21) Appl. No.: 14/455,702 Kuroki. H. et al., “Stimuli-Responsive Materials with Self-Healing Antifouling Surface via 3D Polymer Grafting.” Adv. Funct. Mater. (22) Filed: Aug. 8, 2014 (2013) pp. 4593-4600, 23. Li, M. et al., "Surface Modification of Silicone for Biomedical (51) Int. Cl. Applications Requiring Long-Term Antibacterial, Antifouling, and C09D 5/16 (2006.01) Hemocompatible Properties.” Langmuir (2012) pp. 16408-16422, 28. (52) U.S. Cl. Liu, Y. et al., "Surface Structures of PDMS Incorporated with CPC ......... C09D 5/1637 (2013.01); C09D 5/1693 Quaternary Ammonium Salts Designed for Antibiofouling and (2013.01) Fouling Release Applications.” Langmuir (2013) pp. 2897-2905, 29. (58) Field of Classification Search Magin, C.M. et al., “Non-toxic antifouling strategies.” Mater. Today CPC ............................ C09D 5/1637; C09D 5/1693 (2010) pp. 36-44, 13:4. See application file for complete search history. Majumdar, P. et al., “Combinatorial Materials Research Applied to the Development of New Surface Coatings XV: An Investigation of (56) References Cited Polysiloxane Anti-Fouling/Fouling-Release Coatings Containing Tethered Quaternary Ammonium Salt Groups.” ACS Comb. Sci. U.S. PATENT DOCUMENTS (2011) pp. 298–309, 13. McBain, A.J. et al., “Effects of Quaternary-Ammonium-Based 4,528,118 A * 7/1985 Murase ..................... CO8F 8.00 Formulations on Bacterial Community Dynamics and Antimicrobial 252/SOO Susceptibility.” Appl. Environ. Microbiol. (2004) pp. 3449-3456, 5,064,572 A * 11/1991 Ohnishi ................. HO1B 1.128 TO:6. 252/SOO Pant, R.R. et al., “Synthesis and Biocidal Efficacy of Self-Spreading 7,314,505 B1 1/2008 Wheeler et al. Polydimethylsiloxane Oligomers Possessing Oxyethylene 7.550,071 B1 6, 2009 Dirk et al. Functionalized Quaternary Ammoniums,” J. Appl. Polym. Sci. 7,955,945 B1 6, 2011 Dirk et al. (2009) pp. 2397-2403, 113. 8,223,472 B1 7, 2012 Dirk et al. Pranzetti, A. et al., “An Electrically Reversible Switchable Surface 8.426,321 B1 4/2013 Dirk et al. to Control and Study Early Bacterial Adhesion Dynamics in Real 8.427.809 B1 4/2013 Dirk et al. Time.” Adv. Mater. (2013) pp. 2181-2185, 25. 8,703,391 B1 4/2014 Dirk et al. Salta, M. et al., “Assessment of marine biofilm attachment and growth for antifouling Surfaces under static and controlled hydro OTHER PUBLICATIONS dynamic conditions.” Mater. Res. Soc. Symp. Proc. (2011) pp. 1-7. 1356. Banerjee, I. et al., “Antifouling Coatings: Recent Developments in (Continued) the Design of Surfaces That Prevent Fouling by Proteins, Bacteria, and Marine Organisms,” Adv. Mater. (2011) pp. 690-718, 23. Primary Examiner — Margaret Moore Burn, P.L. et al., “Precursor Route Chemistry and Electronic Prop (74) Attorney, Agent, or Firm — Helen S. Baca erties of Poly(p-phenylene-vinylene), Poly(2,5-dimethyl-p- (57) ABSTRACT phenylene)vinylene and Poly (2,5-dimethoxy-p- phenylene)vinylene).” J. Chem. Soc. Perkin (1992) pp. 3225-3231, The present invention relates to antifouling coatings capable Trans. 1. of being switched by using heat or ultraviolet light. Prior to Charnley, M. et al., “Designed polymer structures with antifouling Switching, the coating includes an onium cation component antimicrobial properties,” Reactive Funct. Polym. (2011) pp. 329 having antimicrobial and antibacterial properties. Upon 334, 71. Switching, the coating is converted to a conjugated polymer Cheng, G. et al., “A Switchable Biocompatible Polymer Surface state, and the cationic component is released with any with Self-Sterilizing and Nonfouling Capabilities.” Angew. Chem. adsorbed biofilm layer. Thus, the coatings herein have Int. Ed. (2008) pp. 8831-8834, 47. Dafforn, K.A. et al., “Antifouling strategies: History and regulation, switchable and releasable properties. Methods of making ecological impacts and mitigation.” Marine Pollut. Bull. (2011) pp. and using Such coatings are also described. 453-465, 62. 16 Claims, 18 Drawing Sheets US 9,580,608 B1 Page 2 (56) References Cited methacrylate).” Colloid. Surf. B: Bionterfaces (2013) pp. 361-370, 102. Wessling, R.A., “The Polymerization of Xylylene Bisdialkyl OTHER PUBLICATIONS Sulfonium Salts.” J. Polym. Sci.: Polym. Symp. (1985) pp.55-66, 72. Salta, M. et al., “Marine biofilms on artificial Surfaces: structure and Xie, L. et al., “Coatings with a self-generating hydrogel Surface for dynamics,” Environ. Microbiol. (2013) pp. 2879-2893, 15:11. antifouling.” Polymer (2011) pp. 3738-3744, 52. Siedenbiedel, F. and Tiller, J.C., “Antimicrobial Polymers in Solu Xue, L. et al., "Bio-inspired self-cleaning PAAS hydrogel released tion and on Surfaces: Overview and Functional Principles.” Poly coating for marine antifouling.” J. Colloid Interface Sci. (2014) pp. mers (2012) pp. 46-71. 4. 178-183,421. Sundaram, H.S. et al., “Effect of Amphiphilic Structures on Anti Zhao, X. et al., "Hierarchically engineered membrane Surfaces with fouling and Fouling Release Properties of PS-B-P(E/B)-B-PI Based Superior antifouling and self-cleaning properties' J. Membr. Sci. Triblock Copolymer.” Polymer (2011) pp. 1034-1035, 52(2). (2013) pp. 93-101, 441. Tu, Q. et al., “Antifouling properties of poly(dimethylsiloxane) Surfaces modified with quaternized poly(dimethylaminoethyl * cited by examiner U.S. Patent Feb. 28, 2017 Sheet 1 of 18 US 9,580,608 B1 FC, A re-treat FG. B R2a S-R's Ys-Ra ( ) ( A”A or hy 4. ( ) \ FG. C U.S. Patent Feb. 28, 2017 Sheet 2 of 18 US 9,580,608 B1 U.S. Patent Feb. 28, 2017 Sheet 3 of 18 US 9,580,608 B1 BF O V () BF SO) (I-3) FG, 2) (-4) U.S. Patent Feb. 28, 2017 Sheet 4 of 18 US 9,580,608 B1 y N-1N1S N1-1N \ (E ---- Ci/ & ) C Meph(2a) x- C so V() / (a) 42% w (3.a) (S C BF NaOH VG) NaBF4 VG) acetone, H2O A re. S H2O (K s \ / f M / (-1a). " (-1) A ow m a. m. m. m. m. m. m. sh. () ) (H-1) F.G. 3A 0.9 : OO : : equartz blank 2OC No treater is s - OOC 80 : ''''' a 120C 2 - - - - - - 40C S. 60 s : d s 3 as 40 t s 2 20 35C O i- O R O 80 200 300 400 500 2OO 3OO AOO 500 Temperature (C) Wavelength (nm) FG, 3B U.S. Patent Feb. 28, 2017 Sheet 5 of 18 US 9,580,608 B1 () C ()2b - c. ()S BF, SG, C 7-O-- Ee - c. SGE) ()- : NEatta - (a) 86, C (3.b) MeOH, H2O - (-2) f FG, 3C c C y C} SG) (a) V (3a) NaO-DMF C ( ) MeOH, HO U.S. Patent Feb. 28, 2017 Sheet 7 of 18 US 9,580,608 B1 F.G. 5) U.S. Patent Feb. 28, 2017 Sheet 8 of 18 US 9,580,608 B1 -O-Si-O- a Nai -O-Si-O-- * -o-si-o- Nafion)HO to slo S), C "" . (5a) (5b) (8a) acetonitrileNES - {n-to-5-9 si, O s R A.O. ( O StoA ?old Si --A to-O Si, O ---t e'sm NEt NE 3 o-3 (EV-3) (-3a) (EI-3) FG. 6A i. Na . Nafion(R) i. to so- acetie t H2O ot, a Y (5a) (5b) (6a) of } \ f : -acetonitrie NE-- - o St. AgOHO to ana Si l, : rtola- tt - i.R (3 i. O- (V-1) (Ris-NEt3 or -S(CH3(Cshi)) U.S. Patent Feb. 28, 2017 Sheet 9 of 18 US 9,580,608 B1 ::::::::::::::::::::: U.S. Patent Feb. 28, 2017 Sheet 10 of 18 US 9,580,608 B1 Sulfonium Biotoxicity 8.00 ; 500 PC bark PC coated SS blank SS coated FG. 7 U.S. Patent Feb. 28, 2017 Sheet 11 of 18 US 9,580,608 B1 leachate testing antibiofouling testing Coated Side in Coated side in artificial sea water artificial Sea water with marine organisms 24 hr 24 hr incubation incubation Biofilm growth C Artificial sea water "extracted' introduce organisms Solution growth Biofilm growth Or s & & se Solution growth FG. 8 U.S. Patent Feb. 28, 2017 Sheet 12 of 18 US 9,580,608 B1 teachate toxicity of suitonium and PPV solution growth of marine bacteria C.
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