Thiol-ene "click" networks from amphiphilic fluoropolymers: Full synthesis and characterization of a benchmark anti-biofouling surface

Journal of Materials Chemistry

Volumn 22, Issue 37, 2012, Pages 19462-19473

  Imbesi, Philip M ^a   Raymond, Jeffery E ^a   Tucker, Bryan S ^a   Wooley, Karen L ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIPHILICS; ANTI-BIOFOULING; ANTI-BIOFOULING COATINGS; BIOCIDAL; BLEND RATIOS; CROSS-LINKED NETWORKS; HETEROGENEOUS SURFACE; LABELLED PROTEIN; MODEL SURFACE; NANO-SCALE SURFACES; PROCESS CONDITION; PROTEIN ADSORPTION; REAL-WORLD APPLICATION; RELATIVE FLUORESCENCE INTENSITY; SINGLE COMPONENTS; SURFACE MECHANICAL PROPERTIES; SURFACE OPTIMIZATION; THIOL-ENES; TUNABILITIES; YOUNG'S MODULUS;

ADSORPTION; BIOFOULING; CROSSLINKING; FLUORINE CONTAINING POLYMERS; INFRARED SPECTROSCOPY; INORGANIC COATINGS; MECHANICAL PROPERTIES; OLIGOMERS; OPTIMIZATION; SILICONES; SYNTHESIS (CHEMICAL);

BENCHMARKING;

EID: 84865709403     PISSN: 09599428     EISSN: 13645501     Source Type: Journal    
DOI: 10.1039/c2jm32005c     Document Type: Article

References (37)

1. D. M. Yebra S. Kiil K. Dam-Johansen Antifouling technology - past, present and future steps towards efficient and environmentally friendly antifouling coatings Prog. Org. Coat. 2004 50 75
2. http://www.onr.navy.mil/media-center/fact-sheets/biofouling-prevention. aspx, accessed 12 February 2012
3. M. P. Schultz Effects of coating roughness and biofouling on ship resistance and powering Biofouling 2007 23 331
4. M. P. Schultz J. A. Bendick E. R. Holm W. M. Hertel Economic impact of biofouling on a naval surface ship Biofouling 2011 27 87
5. Y. Wang L. M. Pitet J. Finlay L. H. Brewer G. Cone D. E. Betts M. E. Callow J. A. Callow D. E. Wendt M. A. Hillmeyer J. M. De Simone Investigation of the role of hydrophilic chain length in amphiphilic perfluoropolyether/ poly(ethylene glycol) networks: towards high-performance antifouling coatings Biofouling 2011 27 1139
6. S. J. Feng Q. Wang Y. Gao Y. G. Huang F. L. Qing Synthesis and characterization of a novel amphiphilic copolymer capable as anti-biofouling coating material J. Appl. Polym. Sci. 2009 114 2071
7. R. F. Brady I. L. Singer Mechanical factors favoring release from fouling release coatings Biofouling 2000 15 73
8. J. Genzer K. Efimenko Recent developments in superhydrophobic surfaces and their relevance to marine fouling: a review Biofouling 2006 22 339
9. L. Hoipkemeier-Wilson J. F. Schumacher M. L. Carman A. L. Gibson A. W. Feinberg M. E. Callow J. A. Finlay J. A. Callow A. B. Brennan Antifouling potential of lubricious, micro-engineered, PDMS elastomers against zoospores of the green fouling alga Ulva (Enteromorpha) Biofouling 2004 20 53
10. A. J. Scardino H. Zhang D. J. Cookson R. N. Lamb R. de Nys The role of nano-roughness in antifouling Biofouling 2009 25 757
11. M. D. Dimitriou Z. Zhou H.-S. Yoo K. L. Killops J. A. Finlay G. Cone H. S. Sundaram N. A. Lynd K. P. Barteau L. M. Campos D. A. Fischer M. E. Callow J. A. Callow C. K. Ober C. J. Hawker E. J. Kramer A general approach to controlling the surface composition of poly(ethylene oxide)-based block copolymers for antifouling coatings Langmuir 2011 27 13762
12. Z. Zhang J. A. Finlay L. Wang Y. Gao J. A. Callow M. E. Callow S. Jiang Polysulfobetaine-grafted surfaces as environmentally benign ultralow fouling marine coatings Langmuir 2009 25 13516
13. J. W. Bartels C. Cheng K. T. Powell J. Q. Xu K. L. Wooley Hyperbranched fluoropolymers and their hybridization into complex amphiphilic crosslinked copolymer networks Macromol. Chem. Phys. 2007 208 1676
14. C. S. Gudipati J. A. Finlay J. A. Callow M. E. Callow K. L. Wooley The antifouling and fouling-release perfomance of hyperbranched fluoropolymer (HBFP)-poly(ethylene glycol) (PEG) composite coatings evaluated by adsorption of biomacromolecules and the green fouling alga Ulva Langmuir 2005 21 3044
15. C. S. Gudipati C. M. Greenlief J. A. Johnson P. Prayongpan K. L. Wooley Hyperbranched fluoropolymer and linear poly(ethylene glycol) based amphiphilic crosslinked networks as efficient antifouling coatings: an insight into the surface compositions, topographies, and morphologies J. Polym. Sci., Part A: Polym. Chem. 2004 42 6193
16. A. Mueller T. Kowalewski K. L. Wooley Synthesis, characterization, and derivatization of hyperbranched polyfluorinated polymers Macromolecules 1998 31 776
17. J. Xu J. W. Bartels D. A. Bohnsack T.-C. Tseng M. E. Mackay K. L. Wooley Hierarchical inorganic-organic nanocomposites possessing amphiphilic and morphological complexities: influence of nanofiller dispersion on mechanical performance Adv. Funct. Mater. 2008 18 2733
18. J. Q. Xu D. A. Bohnsack M. E. Mackay K. L. Wooley Unusual mechanical performance of amphiphilic crosslinked polymer networks J. Am. Chem. Soc. 2007 129 506
19. C. R. Morgan A. D. Ketley The effect of phosphines on thiol/ene curing systems J. Polym. Sci., Polym. Lett. Ed. 1978 16 75
20. C. R. Morgan F. Magnotta A. D. Ketley Thiol/ene photocurable polymers J. Polym. Sci., Polym. Chem. Ed. 1977 15 627
21. E. Cakmakci Y. Mulazim M. V. Kahraman N. K. Apohan Flame retardant thiol-ene photocured coatings React. Funct. Polym. 2011 71 36
22. M. J. Kade D. J. Burke C. J. Hawker The power of thiol-ene chemistry J. Polym. Sci., Part A: Polym. Chem. 2010 48 743
23. K. L. Killops L. M. Campos C. J. Hawker Robust, efficient, and orthogonal synthesis of dendrimers via thiol-ene "click" chemistry J. Am. Chem. Soc. 2008 130 5062
24. J. W. Bartels P. M. Imbesi J. Finlay C. Fidge J. Ma J. E. Seppala A. M. Nystrom M. E. Mackay J. A. Callow M. E. Callow K. L. Wooley Antibiofouling hybrid dendritic Boltorn/star PEG thiol-ene cross-linked networks ACS Appl. Mater. Interfaces 2011 3 2118
25. L. M. Campos I. Meinel R. G. Guino M. Schierhorn N. Gupta G. D. Stucky C. J. Hawker Highly versatile and robust materials for soft imprint lithography based on thiol-ene click chemistry Adv. Mater. 2008 20 3728
26. E. C. Hagberg M. Malkoch Y. B. Ling C. J. Hawker K. R. Carter Effects of modulus and surface chemistry of thiol-ene photopolymers in nanoimprinting Nano Lett. 2007 7 233
27. A. K. O'Brien N. B. Cramer C. N. Bowman Oxygen inhibition in thiol-acrylate photopolymerizations J. Polym. Sci., Part A: Polym. Chem. 2006 44 2007
28. N. B. Cramer J. P. Scott C. N. Bowman Photopolymerizations of thiol-ene polymers without photoinitiators Macromolecules 2002 35 5361
29. C. E. Hoyle T. Y. Lee T. Roper Thiol-enes: chemistry of the past with promise for the future J. Polym. Sci., Part A: Polym. Chem. 2004 42 5301
30. H. Ihre, M. Johansson, E. Malström and A. Hult, Dendrimers and Hyperbranched Aliphatic Polyesters Based on 2,2-bis(hydroxymethyl)propionic acid (Bis-MPA), JAI Press Inc., 1996
31. L. Mespouille J. L. Hedrick P. Dubois Expanding the role of chemistry to produce new amphiphilic polymer (co)networks Soft Matter 2009 5 4878
32. J. Ma J. W. Bartels Z. Li K. Zhang C. Cheng K. L. Wooley Synthesis and solution-state assembly or bulk state thiol-ene crosslinking of pyrrolidinone- and alkene-functionalized amphiphilic block fluorocopolymers: from functional nanoparticles to anti-fouling coatings Aust. J. Chem. 2010 63 1159
33. P. M. Imbesi C. Fidge J. E. Raymond S. I. Cauet K. L. Wooley Model Diels-Alder studies for the creation of amphiphilic cross-linked networks as healable, antibiofouling coatings ACS Macro Lett. 2012 1 473
34. J.-C. Tan P. J. Saines E. G. Bithell A. K. Cheetham Hybrid nanosheets of an inorganic-organic framework material: facile synthesis, structure, and elastic properties ACS Nano 2012 6 615
35. T. J. Young M. A. Monclus T. L. Burnett W. R. Broughton S. L. Ogin The use of the PeakForce™ quantitative nanomechanical mapping AFM-based method for high-resolution Young's modulus measurement of polymers Meas. Sci. Technol. 2011 22 125703
36. A. W. Neumann R. J. Good Techniques of measuring contact angles [in surface studies] Surf. Colloid Sci. 1979 11 31
37. P. M. Imbesi N. V. Gohad M. J. Eller B. Orihuela D. Rittschof E. A. Schweikert A. S. Mount K. L. Wooley Noradrenaline-functionalized hyperbranched fluoropolymer-poly(ethylene glycol) cross-linked networks as dual-mode, anti-biofouling coatings ACS Nano 2012 6 1503