Underwater Superoleophobic Surfaces Prepared from Polymer Zwitterion/Dopamine Composite Coatings

Hydration is central to mitigating surface fouling by oil and microorganisms. Immobilization of hydrophilic polymers on surfaces promotes retention of water and a reduction of direct interactions with potential foulants. While conventional surface modification techniques are surface‐specific, mussel‐inspired adhesives based on dopamine effectively coat many types of surfaces and thus hold potential as a universal solution to surface modification. Here, a facile, one‐step surface modification strategy is described that affords hydrophilic, and underwater superoleophobic, coatings by the simultaneous deposition of polydopamine (PDA) with poly(methacryloyloxyethyl phosphorylcholine) (polyMPC). The resultant composite coating features enhanced hydrophilicity (i.e., water contact angle of ≈10° in air) and antifouling performance relative to PDA coatings. PolyMPC affords control over coating thickness and surface roughness and results in a nearly tenfold reduction in Escherichia coli adhesion relative to unmodified glass. The substrate‐independent nature of PDA coatings further promotes facile surface modification without tedious surface pretreatment and offers a robust template for codepositing polyMPC to enhance biocompatibility, hydrophilicity, and fouling resistance.

[1]  Gustavo Fernández,et al.  Strategies to create hierarchical self-assembled structures via cooperative non-covalent interactions. , 2015, Chemical Society reviews.

[2]  N. Huang,et al.  Insights into the aggregation/deposition and structure of a polydopamine film. , 2014, Langmuir : the ACS journal of surfaces and colloids.

[3]  Zhi‐Kang Xu,et al.  Fabrication of antifouling membrane surface by poly(sulfobetaine methacrylate)/polydopamine co-deposition , 2014 .

[4]  Ann K. Nowinski,et al.  Achieving One‐Step Surface Coating of Highly Hydrophilic Poly(Carboxybetaine Methacrylate) Polymers on Hydrophobic and Hydrophilic Surfaces , 2014, Advanced materials interfaces.

[5]  G. Vitiello,et al.  Tris buffer modulates polydopamine growth, aggregation, and paramagnetic properties. , 2014, Langmuir : the ACS journal of surfaces and colloids.

[6]  K. Ishihara,et al.  Reduced platelets and bacteria adhesion on poly(ether ether ketone) by photoinduced and self-initiated graft polymerization of 2-methacryloyloxyethyl phosphorylcholine. , 2014, Journal of biomedical materials research. Part A.

[7]  J. Schlenoff Zwitteration: Coating Surfaces with Zwitterionic Functionality to Reduce Nonspecific Adsorption , 2014, Langmuir : the ACS journal of surfaces and colloids.

[8]  Jiwei Cui,et al.  Nanoscale engineering of low-fouling surfaces through polydopamine immobilisation of zwitterionic peptides. , 2014, Soft matter.

[9]  H. Matsuyama,et al.  Enhanced antibiofouling of RO membranes via polydopamine coating and polyzwitterion immobilization , 2014 .

[10]  Jiang Yuan,et al.  Hemocompatibility improvement of poly(ethylene terephthalate) via self-polymerization of dopamine and covalent graft of zwitterions. , 2014, Materials science & engineering. C, Materials for biological applications.

[11]  Lehui Lu,et al.  Polydopamine and its derivative materials: synthesis and promising applications in energy, environmental, and biomedical fields. , 2014, Chemical reviews.

[12]  Young Chang Seo,et al.  Material-independent fabrication of superhydrophobic surfaces by mussel-inspired polydopamine , 2014 .

[13]  W. Tsai,et al.  Poly(dopamine) coating to biodegradable polymers for bone tissue engineering , 2014, Journal of biomaterials applications.

[14]  Lei Jiang,et al.  Salt-induced fabrication of superhydrophilic and underwater superoleophobic PAA-g-PVDF membranes for effective separation of oil-in-water emulsions. , 2014, Angewandte Chemie.

[15]  Yi-Ming Sun,et al.  Zwitterionic-based stainless steel with well-defined polysulfobetaine brushes for general bioadhesive control. , 2014, ACS applied materials & interfaces.

[16]  Jinhong Jiang,et al.  Antifouling and antimicrobial polymer membranes based on bioinspired polydopamine and strong hydrogen-bonded poly(N-vinyl pyrrolidone). , 2013, ACS applied materials & interfaces.

[17]  Qing-Wen Zhang,et al.  Curcumin-loaded solid lipid nanoparticles have prolonged in vitro antitumour activity, cellular uptake and improved in vivo bioavailability. , 2013, Colloids and surfaces. B, Biointerfaces.

[18]  Jiang Yuan,et al.  Hemocompatibility and anti-biofouling property improvement of poly(ethylene terephthalate) via self-polymerization of dopamine and covalent graft of zwitterionic cysteine. , 2013, Colloids and surfaces. B, Biointerfaces.

[19]  Lei Jiang,et al.  Nanowire‐Haired Inorganic Membranes with Superhydrophilicity and Underwater Ultralow Adhesive Superoleophobicity for High‐Efficiency Oil/Water Separation , 2013, Advanced materials.

[20]  Radosław Mrówczyński,et al.  Structure of polydopamine: a never-ending story? , 2013, Langmuir : the ACS journal of surfaces and colloids.

[21]  Meifang Zhu,et al.  Assembly of poly(dopamine)/poly(N-isopropylacrylamide) mixed films and their temperature-dependent interaction with proteins, liposomes, and cells. , 2013, Langmuir : the ACS journal of surfaces and colloids.

[22]  W. Tsai,et al.  Poly(dopamine)-assisted immobilization of Arg-Gly-Asp peptides, hydroxyapatite, and bone morphogenic protein-2 on titanium to improve the osteogenesis of bone marrow stem cells. , 2013, ACS applied materials & interfaces.

[23]  Lei Tao,et al.  Mussel-inspired chemistry and Michael addition reaction for efficient oil/water separation. , 2013, ACS applied materials & interfaces.

[24]  G. N. Sastry,et al.  Cation-π interaction: its role and relevance in chemistry, biology, and material science. , 2013, Chemical reviews.

[25]  M. Alfè,et al.  Building‐Block Diversity in Polydopamine Underpins a Multifunctional Eumelanin‐Type Platform Tunable Through a Quinone Control Point , 2013 .

[26]  Yung Chang,et al.  Blood‐Inert Surfaces via Ion‐Pair Anchoring of Zwitterionic Copolymer Brushes in Human Whole Blood , 2013 .

[27]  M. Buehler,et al.  Self-Assembly of Tetramers of 5,6-Dihydroxyindole Explains the Primary Physical Properties of Eumelanin: Experiment, Simulation, and Design ARTICLE , 2022 .

[28]  Tae Hwan Choi,et al.  Oxygen concentration control of dopamine-induced high uniformity surface coating chemistry. , 2013, ACS applied materials & interfaces.

[29]  Yan Zhang,et al.  Assembly of poly(dopamine) films mixed with a nonionic polymer. , 2012, Langmuir : the ACS journal of surfaces and colloids.

[30]  In Taek Song,et al.  Non‐Covalent Self‐Assembly and Covalent Polymerization Co‐Contribute to Polydopamine Formation , 2012 .

[31]  V. Ball,et al.  Kinetics of polydopamine film deposition as a function of pH and dopamine concentration: insights in the polydopamine deposition mechanism. , 2012, Journal of colloid and interface science.

[32]  M. Schubert-Zsilavecz,et al.  Effect of phospholipid-based formulations of Boswellia serrata extract on the solubility, permeability, and absorption of the individual boswellic acid constituents present. , 2012, Journal of natural products.

[33]  M. Otyepka,et al.  Functionalization of graphene: covalent and non-covalent approaches, derivatives and applications. , 2012, Chemical reviews.

[34]  M. V. van Loosdrecht,et al.  Short-term adhesion and long-term biofouling testing of polydopamine and poly(ethylene glycol) surface modifications of membranes and feed spacers for biofouling control. , 2012, Water research.

[35]  Benny D. Freeman,et al.  Impact of feed spacer and membrane modification by hydrophilic, bactericidal and biocidal coating on biofouling control , 2012 .

[36]  P. Messersmith,et al.  Universal surface-initiated polymerization of antifouling zwitterionic brushes using a mussel-mimetic peptide initiator. , 2012, Langmuir : the ACS journal of surfaces and colloids.

[37]  B. Freeman,et al.  Elucidating the structure of poly(dopamine). , 2012, Langmuir : the ACS journal of surfaces and colloids.

[38]  Sung Min Kang,et al.  One‐Step Multipurpose Surface Functionalization by Adhesive Catecholamine , 2012, Advanced functional materials.

[39]  Sabine Szunerits,et al.  Reduction and functionalization of graphene oxide sheets using biomimetic dopamine derivatives in one step. , 2012, ACS applied materials & interfaces.

[40]  Xiaotao Zhu,et al.  Superhydrophilic-superoleophobic coatings , 2012 .

[41]  Li-ping Zhu,et al.  Fabrication of superhydrophilic poly(styrene-alt-maleic anhydride)/silica hybrid surfaces on poly(vinylidene fluoride) membranes. , 2011, Journal of colloid and interface science.

[42]  P. Messersmith,et al.  Antibacterial performance of polydopamine-modified polymer surfaces containing passive and active components. , 2011, ACS applied materials & interfaces.

[43]  Jinhong Jiang,et al.  Surface characteristics of a self-polymerized dopamine coating deposited on hydrophobic polymer films. , 2011, Langmuir : the ACS journal of surfaces and colloids.

[44]  Jaroslaw Drelich,et al.  Hydrophilic and superhydrophilic surfaces and materials , 2011 .

[45]  Lei Jiang,et al.  A Novel Superhydrophilic and Underwater Superoleophobic Hydrogel‐Coated Mesh for Oil/Water Separation , 2011, Advanced materials.

[46]  Sung Min Kang,et al.  Enhancement of blood compatibility of poly(urethane) substrates by mussel-inspired adhesive heparin coating. , 2011, Bioconjugate chemistry.

[47]  G. Lorigan,et al.  Probing the interaction of polyphenols with lipid bilayers by solid-state NMR spectroscopy. , 2011, Journal of agricultural and food chemistry.

[48]  K. Ishihara,et al.  Detailed study of the reversible addition–fragmentation chain transfer polymerization and co-polymerization of 2-methacryloyloxyethyl phosphorylcholine , 2011 .

[49]  Sung Min Kang,et al.  Simultaneous Reduction and Surface Functionalization of Graphene Oxide by Mussel‐Inspired Chemistry , 2011 .

[50]  Sung Min Kang,et al.  One-step modification of superhydrophobic surfaces by a mussel-inspired polymer coating. , 2010, Angewandte Chemie.

[51]  Jie Li,et al.  Oxidant-induced dopamine polymerization for multifunctional coatings , 2010 .

[52]  K. Ishihara,et al.  Surface grafting of biocompatible phospholipid polymer MPC provides wear resistance of tibial polyethylene insert in artificial knee joints. , 2010, Osteoarthritis and cartilage.

[53]  M. Semalty,et al.  Supramolecular phospholipids-polyphenolics interactions: the PHYTOSOME strategy to improve the bioavailability of phytochemicals. , 2010, Fitoterapia.

[54]  Shaoyi Jiang,et al.  Ultralow‐Fouling, Functionalizable, and Hydrolyzable Zwitterionic Materials and Their Derivatives for Biological Applications , 2010, Advanced materials.

[55]  Shaoyi Jiang,et al.  Functionalizable and ultra-low fouling zwitterionic surfaces via adhesive mussel mimetic linkages. , 2010, Biomaterials.

[56]  Kazuhiko Ishihara,et al.  Self-initiated surface grafting with poly(2-methacryloyloxyethyl phosphorylcholine) on poly(ether-ether-ketone). , 2010, Biomaterials.

[57]  K. Ishihara,et al.  Cell adhesion on phase-separated surface of block copolymer composed of poly(2-methacryloyloxyethyl phosphorylcholine) and poly(dimethylsiloxane). , 2009, Biomaterials.

[58]  Sung Min Kang,et al.  Norepinephrine: material-independent, multifunctional surface modification reagent. , 2009, Journal of the American Chemical Society.

[59]  Shaoyi Jiang,et al.  Polysulfobetaine-grafted surfaces as environmentally benign ultralow fouling marine coatings. , 2009, Langmuir : the ACS journal of surfaces and colloids.

[60]  J. Brender,et al.  Determining the effects of lipophilic drugs on membrane structure by solid-state NMR spectroscopy: the case of the antioxidant curcumin. , 2009, Journal of the American Chemical Society.

[61]  R. Bitton,et al.  Change of colloidal and surface properties of Mytilus edulis foot protein 1 in the presence of an oxidation (NaIO4) or a complex-binding (Cu2+) agent. , 2009, Biomacromolecules.

[62]  Lei Jiang,et al.  Bioinspired Design of a Superoleophobic and Low Adhesive Water/Solid Interface , 2009 .

[63]  Shaoyi Jiang,et al.  Ultra low fouling zwitterionic polymers with a biomimetic adhesive group. , 2008, Biomaterials.

[64]  J. Homola,et al.  Ultralow fouling and functionalizable surface chemistry based on a zwitterionic polymer enabling sensitive and specific protein detection in undiluted blood plasma. , 2008, Analytical chemistry.

[65]  K. Ishihara,et al.  Rapid development of hydrophilicity and protein adsorption resistance by polymer surfaces bearing phosphorylcholine and naphthalene groups. , 2008, Langmuir : the ACS journal of surfaces and colloids.

[66]  Tae Gwan Park,et al.  Substrate‐Independent Layer‐by‐Layer Assembly by Using Mussel‐Adhesive‐Inspired Polymers , 2008, Advanced materials.

[67]  Haeshin Lee,et al.  Mussel-Inspired Surface Chemistry for Multifunctional Coatings , 2007, Science.

[68]  M. Yamazaki,et al.  Single GUV method reveals interaction of tea catechin (-)-epigallocatechin gallate with lipid membranes. , 2007, Biophysical journal.

[69]  Shaoyi Jiang,et al.  Superlow fouling sulfobetaine and carboxybetaine polymers on glass slides. , 2006, Langmuir : the ACS journal of surfaces and colloids.

[70]  Shiping Zhu,et al.  Protein resistant surfaces: Comparison of acrylate graft polymers bearing oligo-ethylene oxide and phosphorylcholine side chains , 2006, Biointerphases.

[71]  J. Watanabe,et al.  Water structure and improved mechanical properties of phospholipid polymer hydrogel with phosphorylcholine centered intermolecular cross-linker , 2006 .

[72]  Lijun Lin,et al.  Biomimetic anchor for surface-initiated polymerization from metal substrates. , 2005, Journal of the American Chemical Society.

[73]  J. Watanabe,et al.  Enhanced solubility of paclitaxel using water-soluble and biocompatible 2-methacryloyloxyethyl phosphorylcholine polymers. , 2003, Journal of biomedical materials research. Part A.

[74]  Kazuhiko Ishihara,et al.  Preparation of cross-linked biocompatible poly(2-methacryloyloxyethyl phosphorylcholine) gel and its strange swelling behavior in water/ethanol mixture , 2002, Journal of biomaterials science. Polymer edition.

[75]  A. Lewis,et al.  Crosslinkable coatings from phosphorylcholine-based polymers. , 2001, Biomaterials.

[76]  Ebihara,et al.  Photoinduced graft polymerization of 2-methacryloyloxyethyl phosphorylcholine on polyethylene membrane surface for obtaining blood cell adhesion resistance. , 2000, Colloids and surfaces. B, Biointerfaces.

[77]  E. Toone,et al.  Increased adhesion between neutral lipid bilayers: interbilayer bridges formed by tannic acid. , 1994, Biophysical journal.

[78]  K. Ishihara,et al.  Synthesis of graft copolymers having phospholipid polar group by macromonomer method and their properties in water , 1994 .

[79]  Kazuhiko Ishihara,et al.  Preparation of 2-Methacryloyloxyethyl Phosphorylcholine Copolymers with Alkyl Methacrylates and Their Blood Compatibility , 1992 .

[80]  A. Cassie,et al.  Wettability of porous surfaces , 1944 .