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Synthesis and Application of Fluorine-Containing Polymers with Low Surface Energy

Pages 739-757 | Received 27 Mar 2019, Accepted 11 Jun 2019, Published online: 10 Jul 2019

References

  • Blanksby, S. J.; Ellison, G. B. Bond Dissociation Energies of Organic Molecules. Acc. Chem. Res. 2003, 36, 255–263. DOI:10.1021/ar020230d.
  • Owens, D. K.; Wendt, R. C. Estimation of the Surface Free Energy of Polymers. J. Appl. Polym. Sci. 1969, 13, 1741–1747. DOI:10.1002/app.1969.070130815.
  • Lee, S.; Park, J.-S.; Lee, T. R. The Wettability of Fluoropolymer Surfaces: Influence of Surface Dipoles. Langmuir 2008, 24, 4817–4826. DOI:10.1021/la700902h.
  • Ameduri, B. Fluoropolymers: The Right Material for the Right Applications. Chem. Eur. J. 2018, 24, 18830–18841. DOI:10.1002/chem.201802708.
  • Puts, G. J.; Crouse, P.; Ameduri, B. M. Polytetrafluoroethylene: Synthesis and Characterization of the Original Extreme Polymer. Chem. Rev. 2019, 119, 1763–1805. DOI:10.1021/acs.chemrev.8b00458.
  • Roach, P.; Shirtcliffe, N., Superhydrophobicity and self-cleaning. Self-Cleaning Materials and Surfaces 2013, 3–32. DOI:10.1002/9781118652336.
  • Gardiner, J. Fluoropolymers: Origin, Production, and Industrial and Commercial Applications. Aust. J. Chem. 2015, 68, 13–22. DOI:10.1071/CH14165.
  • Ren, K.; Zhou, J.; Wu, H. Materials for Microfluidic Chip Fabrication. Acc. Chem. Res. 2013, 46, 2396–2406. DOI:10.1021/ar300314s.
  • Shahkaramipour, N.; Tran, T. N.; Ramanan, S.; Lin, H. Membranes with Surface-Enhanced Antifouling Properties for Water Purification. Membranes 2017, 7, 13. DOI:10.3390/membranes7010013.
  • Teo, A. J. T.; Mishra, A.; Park, I.; Kim, Y.-J.; Park, W.-T.; Yoon, Y.-J. Polymeric Biomaterials for Medical Implants and Devices. ACS Biomater. Sci. Eng. 2016, 2, 454–472. DOI:10.1021/acsbiomaterials.5b00429.
  • Wong, D. A.; O'Rourke-Muisener, P. A. V.; Koberstein, J. T. Effect of Chain Architecture on Surface Segregation in Functional Polymers: Synthesis and Surface Properties of End- and Center-Functional Poly (d,l-Lactide). Macromolecules 2007, 40, 1604–1614. DOI:10.1021/ma0606915.
  • Iyengar, D. R.; Perutz, S. M.; Dai, C.-A.; Ober, C. K.; Kramer, E. J. Surface Segregation Studies of Fluorine-Containing Diblock Copolymers. Macromolecules 1996, 29, 1229–1234. DOI:10.1021/ma950544z.
  • Zhang, J.; Clark, M. B.; Wu, C.; Li, M.; Trefonas, P.; Hustad, P. D. Orientation Control in Thin Films of a High-χ Block Copolymer with a Surface Active Embedded Neutral Layer. Nano Lett. 2016, 16, 728–735. DOI:10.1021/acs.nanolett.5b04602.
  • Nishimori, K.; Kitahata, S.; Nishino, T.; Maruyama, T. Controlling Surface Segregation of a Polymer to Display Carboxy Groups on an Outermost Surface Using Perfluoroacyl Groups. Langmuir 2018, 34, 6396–6404. DOI:10.1021/acs.langmuir.8b00638.
  • Wang, Z.; Macosko, C. W.; Bates, F. S. Fluorine-Enriched Melt-Blown Fibers from Polymer Blends of Poly(Butylene Terephthalate) and a Fluorinated Multiblock Copolyester. ACS Appl. Mater. Interfaces 2016, 8, 754–761. DOI:10.1021/acsami.5b09976.
  • Hare, E. F.; Shafrin, E. G.; Zisman, W. A. Properties of Films of Adsorbed Fluorinated Acids. J. Phys. Chem. 1954, 58, 236–239. DOI:10.1021/j150513a011.
  • Lindner, E. A Low Surface Free Energy Approach in the Control of Marine Biofouling. Biofouling 1992, 6, 193–205. DOI:10.1080/08927019209386222.
  • Schmidt, D. L.; Coburn, C. E.; DeKoven, B. M.; Potter, G. E.; Meyers, G. F.; Fischer, D. A. Water-Based Non-Stick Hydrophobic Coatings. Nature 1994, 368, 39. DOI:10.1038/368039a0.
  • Tsibouklis, J.; Graham, P.; Eaton, P. J.; Smith, J. R.; Nevell, T. G.; Smart, J. D.; Ewen, R. J. Poly(Perfluoroalkyl Methacrylate) Film Structures: Surface Organization Phenomena, Surface Energy Determinations, and Force of Adhesion Measurements. Macromolecules 2000, 33, 8460–8465. DOI:10.1021/ma0008185.
  • Prathab, B.; Aminabhavi, T. M.; Parthasarathi, R.; Manikandan, P.; Subramanian, V. Molecular Modeling and Atomistic Simulation Strategies to Determine Surface Properties of Perfluorinated Homopolymers and Their Random Copolymers. Polymer 2006, 47, 6914–6924. DOI:10.1016/j.polymer.2006.07.034.
  • van de Grampel, R. D.; Ming, W.; Gildenpfennig, A.; van Gennip, W. J. H.; Krupers, M. J.; Laven, J.; Niemantsverdriet, J. W.; Brongersma, H. H.; van der Linde, R. Surface Studies of Partially Fluorinated Polymethacrylates: A Combined XPS and LEIS Analysis. Prog. Org. Coat. 2002, 45, 273–279. DOI:10.1016/S0300-9440(02)00043-7.
  • van de Grampel, R. D.; Ming, W.; Gildenpfennig, A.; van Gennip, W. J. H.; Laven, J.; Niemantsverdriet, J. W.; Brongersma, H. H.; de With, G.; van der Linde, R. The Outermost Atomic Layer of Thin Films of Fluorinated Polymethacrylates. Langmuir 2004, 20, 6344–6351. DOI:10.1021/la049519p.
  • van de Grampel, R. D.; Ming, W.; Laven, J.; van der Linde, R.; Leermakers, F. A. M. A Self-Consistent-Field Analysis of the Surface Structure and Surface Tension of Partially Fluorinated Copolymers: The Influence of Polymer Architecture. Macromolecules 2002, 35, 5670–5680. DOI:10.1021/ma0121870.
  • van de Grampel, R. D.; Ming, W. H.; Laven, J.; van der Linde, R.; Leermakers, F. A. M. Surface Heterogeneity of a Fluorinated Block Copolymer Melt Studied by a Self-Consistent-Field Analysis. Polymer 2007, 48, 3877–3882. DOI:10.1016/j.polymer.2007.04.065.
  • Van de Grampel, R. D.; Van Geldrop, J.; Laven, J.; Van der Linde, R. P. CF3(CF2)(5)CH(2)MA-co-MMA and P CF3(CF2)(5)CH(2)MA-co-BA Copolymers: Reactivity Ratios and Surface Properties. J. Appl. Polym. Sci. 2001, 79, 159–165. DOI:10.1002/1097-4628(20010103)79:1<159::AID-APP180>3.0.CO;2-W.
  • Chen, A.; Blakey, I.; Jack, K. S.; Whittaker, A. K.; Peng, H. Control through Monomer Placement of Surface Properties and Morphology of Fluoromethacrylate Copolymers. J. Polym. Sci. Part A: Polym. Chem. 2015, 53, 2633–2641. DOI:10.1002/pola.27731.
  • Gu, Z-x.; Cheng, J.; Zhang, M-z.; He, J-l.; Ni, P-h. Effect of Sequence Structure on Wetting Behaviors of Fluorinated Methacrylate Polymers Based on Perfluorohexylethyl Methacrylate and Stearyl Acrylate. Chin. J. Polym. Sci. 2017, 35, 1061–1072. DOI:10.1007/s10118-017-1966-x.
  • Cai, L.; Li, Z. Synthesis and Surface Properties of Novel Fluoroalkylsilyl Methacrylate Copolymers. J. Fluorine Chem. 2015, 178, 187–194. DOI:10.1016/j.jfluchem.2015.07.026.
  • Schmidt, D. L.; Brady, R. F.; Lam, K.; Schmidt, D. C.; Chaudhury, M. K. Contact Angle Hysteresis, Adhesion, and Marine Biofouling. Langmuir 2004, 20, 2830–2836. DOI:10.1021/la035385o.
  • Yarbrough, J. C.; Rolland, J. P.; DeSimone, J. M.; Callow, M. E.; Finlay, J. A.; Callow, J. A. Contact Angle Analysis, Surface Dynamics, and Biofouling Characteristics of Cross-Linkable, Random Perfluoropolyether-Based Graft Terpolymers. Macromolecules 2006, 39, 2521–2528. DOI:10.1021/ma0524777.
  • Gu, Z.; Cheng, J.; Zhang, M.; He, J.; Ni, P. Effect of Groups at α-Position and Side-Chain Structure of Comonomers on Surface Free Energy and Surface Reorganization of Fluorinated Methacrylate Copolymer. Polymer 2017, 114, 79–87. DOI:10.1016/j.polymer.2017.02.073.
  • Graham, P.; Stone, M.; Thorpe, A.; Nevell, T. G.; Tsibouklis, J. Fluoropolymers with Very Low Surface Energy Characteristics. J. Fluorine Chem. 2000, 104, 29–36. DOI:10.1016/S0022-1139(00)00224-4.
  • Yang, T.; Yao, L.; Peng, H.; Cheng, S.; Park, I. J. Characterization of a Low-Wettable Surface Based on Perfluoroalkyl Acrylate Copolymers. J. Fluorine Chem. 2006, 127, 1105–1110. DOI:10.1016/j.jfluchem.2006.05.019.
  • Yao, W.; Li, Y.; Huang, X. Fluorinated Poly(Meth)Acrylate: Synthesis and Properties. Polymer 2014, 55, 6197–6211. DOI:10.1016/j.polymer.2014.09.036.
  • Çanak, T. Ç.; Hamuryudan, E.; Serhatlı, İE. Synthesis and Characterization of Perfluorinated Acrylate–Methyl Methacrylate Copolymers. J. Appl. Polym. Sci. 2013, 128, 1450–1461. DOI:10.1002/app.38128.
  • Çanak, T. Ç.; Ünsal, C.; Serhatlı, İ. E.; Sarac, A. S. Superhydrophobic Fluorinated Acylonitrile Coatings via Electrospraying. Prog. Org. Coat. 2017, 105, 342–352. DOI:10.1016/j.porgcoat.2017.01.013.
  • Chen, T.; Hong, J.; Peng, C.; Chen, G.; Yuan, C.; Xu, Y.; Zeng, B.; Dai, L. Superhydrophobic and Flame Retardant Cotton Modified with DOPO and Fluorine–Silicon-Containing Crosslinked Polymer. Carbohydr. Polym. 2019, 208, 14–21. DOI:10.1016/j.carbpol.2018.12.023.
  • Wang, Y.; Finlay, J. A.; Betts, D. E.; Merkel, T. J.; Luft, J. C.; Callow, M. E.; Callow, J. A.; DeSimone, J. M. Amphiphilic Co-Networks with Moisture-Induced Surface Segregation for High-Performance Nonfouling Coatings. Langmuir 2011, 27, 10365–10369. DOI:10.1021/la202427z.
  • Gong, H.; Zhao, Y.; Shen, X.; Lin, J.; Chen, M. Organocatalyzed Photocontrolled Radical Polymerization of Semifluorinated (Meth)Acrylates Driven by Visible Light. Angew. Chem. Int. Ed. 2018, 57, 333–337. DOI:10.1002/anie.201711053.
  • Gong, H.; Gu, Y.; Chen, M. Controlled/Living Radical Polymerization of Semifluorinated (Meth)Acrylates. Synlett 2018, 29, 1543–1551. DOI:10.1055/s-0036-1591974.
  • Quan, Q.; Gong, H.; Chen, M. Preparation of Semifluorinated Poly(Meth)Acrylates by Improved Photo-Controlled Radical Polymerization without the Use of a Fluorinated RAFT Agent: facilitating Surface Fabrication with Fluorinated Materials. Polym. Chem. 2018, 9, 4161–4171. DOI:10.1039/C8PY00990B.
  • Discekici, E. H.; Anastasaki, A.; Kaminker, R.; Willenbacher, J.; Truong, N. P.; Fleischmann, C.; Oschmann, B.; Lunn, D. J.; Read de Alaniz, J.; Davis, T. P.; et al. Light-Mediated Atom Transfer Radical Polymerization of Semi-Fluorinated (Meth)Acrylates: Facile Access to Functional Materials. J. Am. Chem. Soc. 2017, 139, 5939–5945. DOI:10.1021/jacs.7b01694.
  • Banerjee, S.; Guerre, M.; Ameduri, B.; Ladmiral, V. Syntheses of 2-(Trifluoromethyl)Acrylate-Containing Block Copolymers via RAFT Polymerization Using a Universal Chain Transfer Agent. Polym. Chem. 2018, 9, 3511–3521. DOI:10.1039/C8PY00655E.
  • Banerjee, S.; Bellan, E. V.; Gayet, F.; Debuigne, A.; Detrembleur, C.; Poli, R.; Ameduri, B.; Ladmiral, V. Bis(Formylphenolato)Cobalt(II)-Mediated Alternating Radical Copolymerization of tert-Butyl 2-Trifluoromethylacrylate with Vinyl Acetate. Polymers (Basel, Switzerland) 2017, 9, 702/1–702/11. DOI:10.3390/polym9120702.
  • Perutz, S.; Wang, J.; Kramer, E. J.; Ober, C. K.; Ellis, K. Synthesis and Surface Energy Measurement of Semi-Fluorinated, Low-Energy Surfaces. Macromolecules 1998, 31, 4272–4276. DOI:10.1021/ma9700993.
  • Luo, Z-H.; He, T-Y. Synthesis and Characterization of Poly(Dimethylsiloxane)-Block-Poly(2,2,3,3,4,4,4-Heptafluorobutyl Methacrylate) Diblock Copolymers with Low Surface Energy Prepared by Atom Transfer Radical Polymerization. Reactive Funct. Polym. 2008, 68, 931–942. DOI:10.1016/j.reactfunctpolym.2008.01.004.
  • Owen, M. J. Fluorosilicones. In Advances in Silicones and Silicone-Modified Materials; American Chemical Society: New York, 2010; Vol. 1051, pp 99–108.
  • Yi, L.; Meng, X.; Tian, X.; Zhou, W.; Chen, R. Wettability of Electrospun Films of Microphase-Separated Block Copolymers with 3,3,3-Trifluoropropyl Substituted Siloxane Segments. J. Phys. Chem. C 2014, 118, 26671–26682. DOI:10.1021/jp5065566.
  • Smirnova, O.; Glazkov, A.; Yarosh, A.; Sakharov, A. Fluorinated Polyurethanes, Synthesis and Properties. Molecules 2016, 21, 904. DOI:10.3390/molecules21070904.
  • Yoon, S. C.; Ratner, B. D. Surface Structure of Segmented Poly(Ether Urethanes) and Poly(Ether Urethane Ureas) with Various Perfluoro Chain Extenders. An X-Ray Photoelectron Spectroscopic Investigation. Macromolecules 1986, 19, 1068–1079. DOI:10.1021/ma00158a023.
  • Yoon, S. C.; Ratner, B. D. Surface and Bulk Structure of Segmented Poly(Ether Urethanes) with Perfluoro Chain Extenders. 2. FTIR, DSC, and X-Ray Photoelectron Spectroscopic Studies. Macromolecules 1988, 21, 2392–2400. DOI:10.1021/ma00186a016.
  • Yoon, S. C.; Ratner, B. D. Surface and Bulk Structure of Segmented Poly(Ether Urethanes) with Perfluoro Chain Extenders. 3. Effects of Annealing, Casting Solvent, and Casting Conditions. Macromolecules 1988, 21, 2401–2404. DOI:10.1021/ma00186a017.
  • Yoon, S. C.; Sung, Y. K.; Ratner, B. D. Surface and Bulk Structure of Segmented Poly(Ether Urethanes) with Perfluoro Chain Extenders. 4. Role of Hydrogen Bonding on Thermal Transitions. Macromolecules 1990, 23, 4351–4356. DOI:10.1021/ma00222a004.
  • Chapman, T. M.; Benrashid, R.; Gribbin, K. L.; Keener, J. P. Determination of Low Critical Surface Energies of Novel Fluorinated Poly(Amide Urethane) Block Copolymers. 1. Fluorinated Side Chains. Macromolecules 1995, 28, 331–335. DOI:10.1021/ma00105a046.
  • Chapman, T. M.; Marra, K. G. Determination of Low Critical Surface Tensions of Novel Fluorinated Poly(Amide Urethane) Block Copolymers. 2. Fluorinated Soft-Block Backbone and Side Chains. Macromolecules 1995, 28, 2081–2085. DOI:10.1021/ma00110a047.
  • Ho, T.; Wynne, K. J. A New Fluorinated Polyurethane: Polymerization, Characterization, and Mechanical Properties. Macromolecules 1992, 25, 3521–3527. DOI:10.1021/ma00039a033.
  • Honeychuck, R. V.; Ho, T.; Wynne, K. J.; Nissan, R. A. Preparation and Characterization of Polyurethanes Based on a Series of Fluorinated Diols. Chem. Mater. 1993, 5, 1299–1306. DOI:10.1021/cm00033a020.
  • Andruzzi, L.; Chiellini, E.; Galli, G.; Li, X.; Kang, S. H.; Ober, C. K. Engineering Low Surface Energy Polymers through Molecular Design: Synthetic Routes to Fluorinated Polystyrene-Based Block Copolymers. J. Mater. Chem. 2002, 12, 1684–1692. DOI:10.1039/b200891b.
  • Li, K.; Wu, P.; Han, Z. Preparation and Surface Properties of Fluorine-Containing Diblock Copolymers. Polymer 2002, 43, 4079–4086. DOI:10.1016/S0032-3861(02)00202-1.
  • Bertolucci, M.; Galli, G.; Chiellini, E.; Wynne, K. J. Wetting Behavior of Films of New Fluorinated Styrene − Siloxane Block Copolymers. Macromolecules 2004, 37, 3666–3672. DOI:10.1021/ma035934x.
  • Borkar, S.; Jankova, K.; Siesler, H. W.; Hvilsted, S. New Highly Fluorinated Styrene-Based Materials with Low Surface Energy Prepared by ATRP. Macromolecules 2004, 37, 788–794. DOI:10.1021/ma034952b.
  • Jankova, K.; Hvilsted, S. Novel Fluorinated Block Copolymer Architectures Fuelled by Atom Transfer Radical Polymerization. J. Fluorine Chem. 2005, 126, 241–250 (Copyright (C) 2015 American Chemical Society (ACS). All Rights Reserved.) DOI:10.1016/j.jfluchem.2004.11.002.
  • Bucholz, T. L.; Loo, Y.-L. Phase Behavior of near-Monodisperse Semifluorinated Diblock Copolymers by Atom Transfer Radical Polymerization. Macromolecules 2006, 39, 6075–6080. (Copyright (C) 2015 American Chemical Society (ACS). All Rights Reserved.) DOI:10.1021/ma0609679.
  • Martinelli, E.; Agostini, S.; Galli, G.; Chiellini, E.; Glisenti, A.; Pettitt, M. E.; Callow, M. E.; Callow, J. A.; Graf, K.; Bartels, F. W. Nanostructured Films of Amphiphilic Fluorinated Block Copolymers for Fouling Release Application. Langmuir 2008, 24, 13138–13147. DOI:10.1021/la801991k.
  • Ni, H.; Xue, D.; Wang, X.; Zhang, W.; Wang, X.; Shen, Z. Composition and Solution Properties of Fluorinated Block Copolymers and Their Surface Structures in the Solid State. Sci. China Ser. B Chem. 2009, 52, 203–211. DOI:10.1007/s11426-008-0126-0.
  • Islam, M. T.; Jeong, Y. T.; Gal, Y. S.; Park, J. M.; Lim, K. T. Effect of Solvent Vapor on the Morphology of Fluorinated Block Copolymer Films from Different Casting Solvent. Mol. Cryst. Liq. Cryst. 2011, 550, 30–37. (Copyright (C) 2015 American Chemical Society (ACS). All Rights Reserved.) DOI:10.1080/15421406.2011.600188.
  • Cheng, W.; Lau, Y.-T. R.; Weng, L.-T.; Ng, K.-M.; Chan, C.-M. The Surface Chemical Composition and Structure of a Fluorocarbon–Hydrocarbon Block Copolymer. Surf. Interface Anal. 2013, 45, 185–189. DOI:10.1002/sia.5133.
  • Hillmyer, M. A.; Lodge, T. P. Synthesis and Self-Assembly of Fluorinated Block Copolymers. J. Polym. Sci. A Polym. Chem. 2002, 40, 1–8. DOI:10.1002/pola.10074.
  • Dimitriou, M. D.; Zhou, Z.; Yoo, H.-S.; Killops, K. L.; Finlay, J. A.; Cone, G.; Sundaram, H. S.; Lynd, N. A.; Barteau, K. P.; Campos, L. M.; et al. A General Approach to Controlling the Surface Composition of Poly(Ethylene Oxide)-Based Block Copolymers for Antifouling Coatings. Langmuir 2011, 27, 13762–13772. DOI:10.1021/la202509m.
  • Ren, Y.; Lodge, T. P.; Hillmyer, M. A. A New Class of Fluorinated Polymers by a Mild, Selective, and Quantitative Fluorination. J. Am. Chem. Soc. 1998, 120, 6830–6831. DOI:10.1021/ja981316y.
  • Ren, Y.; Lodge, T. P.; Hillmyer, M. A. A Simple and Mild Route to Highly Fluorinated Model Polymers. Macromolecules 2001, 34, 4780–4787. DOI:10.1021/ma010229e.
  • Ren, Y.; Lodge, T. P.; Hillmyer, M. A. Effect of Selective Perfluoroalkylation on the Segregation Strength of Polystyrene-1,2-Polybutadiene Block Copolymers. Macromolecules 2002, 35, 3889–3894. (Copyright (C) 2015 American Chemical Society (ACS). All Rights Reserved.) DOI:10.1021/ma011958x.
  • Yokoyama, H.; Sugiyama, K. Surface Hydrophobicity of Fluorinated Block Copolymers Enhanced by Supercritical Carbon Dioxide Annealing. Langmuir 2004, 20, 10001–10006. DOI:10.1021/la0495231.
  • Yokoyama, H.; Tanaka, K.; Takahara, A.; Kajiyama, T.; Sugiyama, K.; Hirao, A. Surface Structure of Asymmetric Fluorinated Block Copolymers. Macromolecules 2004, 37, 939–945. (Copyright (C) 2015 American Chemical Society (ACS). All Rights Reserved.) DOI:10.1021/ma035191f.
  • Liang, J.; He, L.; Zhao, X.; Dong, X.; Luo, H.; Li, W. Novel Linear Fluoro-Silicon-Containing Pentablock Copolymers: Synthesis and Their Properties as Coating Materials. J. Mater. Chem. 2011, 21, 6934–6943. DOI:10.1039/c1jm10635j.
  • Lian, K.-J.; Chen, C.-Q.; Liu, H.; Wang, N.-X.; Yu, H.-J.; Luo, Z.-H. Surface Microphase Separation in PDMS-b-PMMA-b-PHFBMA Triblock Copolymer Films. J. Appl. Polym. Sci. 2011, 120, 156–164. DOI:10.1002/app.32682.
  • Guan, C.-M.; Luo, Z.-H.; Qiu, J.-J.; Tang, P.-P. Novel Fluorosilicone Triblock Copolymers Prepared by Two-Step RAFT Polymerization: Synthesis, Characterization, and Surface Properties. Eur. Polym. J. 2010, 46, 1582–1593. DOI:10.1016/j.eurpolymj.2010.04.003.
  • Krishnan, S.; Paik, M. Y.; Ober, C. K.; Martinelli, E.; Galli, G.; Sohn, K. E.; Kramer, E. J.; Fischer, D. A. NEXAFS Depth Profiling of Surface Segregation in Block Copolymer Thin Films. Macromolecules 2010, 43, 4733–4743. DOI:10.1021/ma902866x.
  • Otake, A.; Miura, M.; Tsuchiya, K.; Ogino, K. Hydrophobic Surface Construction by Phase-Separation of Fluorinated Block Copolymer for Immersion Lithography. J. Photopol. Sci. Technol. 2008, 21, 679–684. (Copyright (C) 2015 American Chemical Society (ACS). All Rights Reserved.) DOI:10.2494/photopolymer.21.679.
  • Land, M.; de Wit, C. A.; Cousins, I. T.; Herzke, D.; Johansson, J.; Martin, J. W. What is the Effect of Phasing out Long-Chain per- and Polyfluoroalkyl Substances on the Concentrations of Perfluoroalkyl Acids and Their Precursors in the Environment? A Systematic Review Protocol. Environ. Evid. 2015, 4, 3. DOI:10.1186/2047-2382-4-3.
  • Demir, T.; Wei, L.; Nitta, N.; Yushin, G.; Brown, P. J.; Luzinov, I. Toward a Long-Chain Perfluoroalkyl Replacement: Water and Oil Repellency of Polyethylene Terephthalate (PET) Films Modified with Perfluoropolyether-Based Polyesters. ACS Appl. Mater. Interfaces 2017, 9, 24318–24330. DOI:10.1021/acsami.7b05799.
  • Hu, Z.-K.; Pitet, L. M.; Hillmyer, M. A.; DeSimone, J. M. High Modulus, Low Surface Energy, Photochemically Cured Materials from Liquid Precursors. Macromolecules 2010, 43, 10397–10405. DOI:10.1021/ma101180k.
  • Krol, B.; Krol, P.; Pikus, S.; Chmielarz, P.; Skrzypiec, K. Synthesis and Characterisation of Coating Polyurethane Cationomers Containing Fluorine Built-in Hard Urethane Segments. Colloid Polym. Sci. 2010, 288, 1255–1269. DOI:10.1007/s00396-010-2244-4.
  • Singh, A.; Naskar, A. K.; Haynes, D.; Drews, M. J.; Smith, D. W. Jr. Synthesis, Characterization and Surface Properties of Poly(Lactic Acid)-Perfluoropolyether Block Copolymers. Polym. Int. 2011, 60, 507–516. DOI:10.1002/pi.2982.
  • Vitale, A.; Priola, A.; Tonelli, C.; Bongiovanni, R. Nanoheterogeneous Networks by Photopolymerization of Perfluoropolyethers and Acrylic Co-Monomers. Polym. Int. 2013, 62, 1395–1401. DOI:10.1002/pi.4436.
  • Wei, L.; Demir, T.; Grant, A.; Tsukruk, V.; Brown, P. J.; Luzinov, I. Attainment of Water and Oil Repellency for Engineering Thermoplastics without Long-Chain Perfluoroalkyls: Perfluoropolyether-Based Triblock Polyester Additives. Langmuir 2018, 34, 12934–12946. DOI:10.1021/acs.langmuir.8b02628.
  • Bongiovanni, R.; Beamson, G.; Mamo, A.; Priola, A.; Recca, A.; Tonelli, C. High Resolution XPS Investigation of Photocured Films Containing Perfluoropolyether Acrylates. Polymer 2000, 41, 409–414. DOI:10.1016/S0032-3861(99)00203-7.
  • Bongiovanni, R.; Di Meo, A.; Pollicino, A.; Priola, A.; Tonelli, C. New Perfluoropolyether Urethane Methacrylates as Surface Modifiers: Effect of Molecular Weight and End Group Structure. Reactive Funct. Polym. 2008, 68, 189–200. DOI:10.1016/j.reactfunctpolym.2007.09.009.

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