Surface properties of polybenzoxazines

Handbook of Benzoxazine Resins

Volumn , Issue , 2011, Pages 579-593

  Wang, Chih Feng ^a   Chang, Feng Chih ^b   Kuo, Shiao Wei ^c  

^a I SHOU UNIVERSITY   (Taiwan)

^b NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

^c NATIONAL SUN YAT SEN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84882555399     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-444-53790-4.00078-3     Document Type: Chapter

References (115)

1. Ciardelli F., Aglietto M., di Mirabello L.M., Passaglia E., Giancristoforo S., Castelvetro V., et al. New fluorinated acrylic polymers for improving weatherability of building stone materials. Prog. Org. Coat. 1997, 32:43-50.
2. Klinger L., Griffith J.R., Rall C.J.N. Fluoropolymer barriers to stress corrosion in optical fibers. Org. Coat. Appl. Polym. Sci. Proc. 1983, 48:407-411.
3. Bonardi C. Fluoroacrylic telomers and their use as hydrofuge and oleofuge products on diverse substrates. Eur. Pat Appl. 1991, EP 426530.
4. Matsumoto Y., Yoshida K., Ishida M. A novel deposition technique for fluorocarbon films and its applications for bulk- and surface-micromachined devices. Sens. Actuators 1998, 66:308-314.
5. Anderson M.H., Lyons C.S., Wigness B.D. Implantable catheters with non-adherent contacting polymer surfaces 1985, U.S. Pat. 4536179.
6. Coulson S.R., Woodward I., Badyal J.P.S., Brewer S.A., Willis C. Super-repellent composite fluoropolymer surfaces. J. Phys. Chem. B 2000, 104:8836-8840.
7. Jin M., Feng X., Xi J., Zhai J., Cho K., Feng L., et al. Super-hydrophobic PDMS surface with ultra-low adhesive force. Macromol. Rapid Commun. 2005, 26:1805-1809.
8. Feng L., Zhang Z., Mai Z., Ma Y., Liu B., Jiang L., et al. A super-hydrophobic and super-oleophilic coating mesh film for the separation of oil and water. Angew. Chem. Int. Ed. 2004, 43:2012-2014.
9. Hillborg H., Tomczak N., Olah A., Schonherr H., Vancso G.J. Nanoscale hydrophobic recovery: a chemical force microscopy study of uv/ozone-treated cross-linked poly(dimethylsiloxane). Langmuir 2004, 20:785-794.
10. Wu S. Contact angles of liquids on solid polymers. Polymer Interface and Adhesion 1982, 133-168. Marcel Dekker, New York. S. Wu (Ed.).
11. Coulson S.R., Woodward I., Badyal J.P.S., Brewer S.A., Willis C. Super-repellent composite fluoropolymer surfaces. J. Phys. Chem. B 2000, 104:8836-8840.
12. Carlson D.P., Schmiegel W. Fluoropolymers, organic. Ullmann's Encyclopedia of Industrial Chemistry 1988, 393-429. VCH Verlagsgesellschaft, Weinheim, Germany. fifth ed. W. Gerhartz (Ed.).
13. Kobayashi H., Owen M.J. Surface properties of fluorosilicones. Trends Polym. Sci. 1995, 3:330-335.
14. Schmidt D.L., Coburn C.E., DeKoven B.M., Potter G.E., Meyers G.F., Fischer D.A. Role of the product in the transformation of a catalyst to its active state. Nature 1994, 368:41-45.
15. Zisman W.A. Influence of constitution on adhesion. Ind. Eng. Chem. 1963, 55:18-38.
16. Fowkes F.M. Determination of interfacial tensions, contact angles, and dispersion forces in surfaces by assuming additivity of intermolecular interactions in surfaces. J. Phys. Chem. 1962, 66:382.
17. Drummond C.J., Georgaklis G., Chan D.Y.C. Fluorocarbons: surface free energies and van der Waals interaction. Langmuir 1996, 11:2617-2621.
18. Höpken J., Möller M. Low-surface-energy polystyrene. Macromolecules 1992, 25:1461-1467.
19. Owens D.K., Wendt R.C. Estimation of the surface free energy of polymers. J. Appl. Polym. Sci. 1969, 13:1741-1747.
20. Kaelble D.H. A reinterpretation of organic liquid-polytetrafluoroethylene surface interactions. J. Adhesion 1970, 2:50-60.
21. Ma K., Chung T., Good R.J. Surface energy of thermotropic liquid crystalline polyesters and polyesteramide. J. Polym. Sci. B Polym. Phys. 1998, 36:2327-2337.
22. van Oss C.J., Chaudhury M.K., Good R.J. Interfacial Lifshitz-van der Waals and polar interactions in macroscopic systems. Chem. Rev. 1988, 88:927-941.
23. van Oss C.J., Ju L., Chaudhury M.K., Good R.J. Estimation of the polar parameters of the surface tension of liquids by contact angle measurements on gels. J. Colloid Interface Sci. 1989, 128:313-319.
24. van Oss C.J., Giese R.F., Good R.J. Reevaluation of the surface tension components and parameters of polyacetylene from contact angles of liquids. Langmuir 1990, 6:1711-1713.
25. Good R.J., van Oss C.J. The modern theory of contact angles and the hydrogen bond components of surface energies. Modern Approaches to Wettability: Theory and Applications 1992, 1-27. Plenum Press, New York. M.E. Schrader, G.I. Loeb (Eds.).
26. Owen M.J. Low surface energy inorganic polymers. Comments Inorg. Chem. 1988, 7:195-213.
27. Tsibouklis J., Nevell T.G. Ultra-low surface energy polymers: the molecular design requirements. Adv. Mater. 2003, 15:647-650.
28. 2- on the surface energy of main-chain liquid crystalline and crystalline polymers. J. Phys. Chem. B 2001, 105:4145-4150.
29. Sun T., Wang G., Feng L., Liu B., Ma Y., Jiang L., et al. Reversible switching between superhydrophilicity and superhydrophobicity. Angew. Chem. Int. Ed. 2004, 43:357-360.
30. Ning X., Ishida H. Phenolic materials via ring-opening polymerization: synthesis and characterization of bisphenol-A based benzoxazines and their polymers. J. Polym. Sci. A Polym. Chem. 1994, 32:1121-1129.
31. Wang Y.X., Ishida H. Cationic ring-opening polymerization of benzoxazines. Polymer 1999, 40:4563-4570.
32. Macko J.A., Ishida H. Structural effects of phenols on the photooxidative degradation of polybenzoxazines. Polymer 2001, 42:227-240.
33. Ishida H., Allen D.J. Physical and mechanical characterization of near-zero shrinkage polybenzoxazines. J. Polym. Sci. B Polym. Phys. 1996, 34:1019-1030.
34. Ishida H., Rodriguez Y. Curing kinetics of a new benzoxazine-based phenolic resin by differential scanning calorimetry. Polymer 1995, 36:3151-3158.
35. Wang C.F., Su Y.C., Kuo S.W., Huang C.F., Sheen Y.C., Chang F.C. Low-surface-free-energy materials based on polybenzoxazines. Angew. Chem. Int. Ed. 2006, 45:2248-2251.
36. Kim H.D., Ishida H. A study on hydrogen-bonded network structure of polybenzoxazines. J. Phys. Chem. A 2002, 106:3271-3280.
37. Liao C.S., Wu J.S., Wang C.F., Chang F.C. Modification of polymer substrates with low surface free energy material by low-temperature cured polybenzoxazine. Macromol. Rapid Commun. 2008, 29:52-56.
38. Fu H.K., Huang C.F., Kuo S.W., Lin H.C., Yei D.R., Chang F.C. Effect of an organically modified nanoclay on low-surface-energy materials of polybenzoxazine. Macromol. Rapid Commun. 2008, 29:1216-1220.
39. Kuo S.W., Lee H.F., Huang W.J., Jeong K.U., Chang F.C. Solid state and solution self-assembly of helical polypeptides tethered to polyhedral oligomeric silsesquioxanes. Macromolecules 2009, 42:1619-1626.
40. Kuo S.W., Cheng R.S. DNA-like interactions enhance the miscibility of supramolecular polymer blends. Polymer 2009, 50:177-188.
41. Chen W.C., Kuo S.W., Jeng U.S., Chang F.C. Self-assembly through competitive interactions of miscible diblock copolymer/homopolymer blends: poly(vinylphenol-b-methyl methacrylate)/poly(vinylpyrrolidone) blend. Macromolecules 2008, 41:1401-1410.
42. Kuo S.W., Chang F.C. Studies of miscibility behavior and hydrogen bonding in blends of poly(vinylphenol) and poly(vinylpyrrolidone). Macromolecules 2001, 34:5224-5228.
43. Kuo S.W., Chang F.C. Significant thermal property and hydrogen bonding strength increase in poly(vinylphenol-co-vinylpyrrolidone) copolymer. Polymer 2003, 44:3021-3030.
44. Lin C.L., Chen W.C., Liao C.S., Su Y.C., Huang C.F., Kuo S.W., et al. Sequence distribution and polydispersity index affect the hydrogen-bonding strength of poly(vinylphenol-co-methyl methacrylate) copolymers. Macromolecules 2005, 38:6435-6444.
45. Kuo S.W., Wu Y.C., Wang C.F., Jeong K.U. Preparing low-surface-energy polymer materials by minimizing intermolecular hydrogen-bonding interactions. J. Phys. Chem. C 2009, 113:20666-20673.
46. Drelich J., Miller J.D., Good R.J. The effect of drop (bubble) size on advancing and receding contact angles for heterogeneous and rough solid surfaces as observed with sessile-drop and captive-bubble techniques. J. Colloid Interface Sci. 1996, 179:37-50.
47. Tsibouklis J., Stone M., Thorpe A.A., Graham P., Ewen R.J., Nevell T.G. Surface energy characteristics of polymer film structures: a further insight into the molecular design requirements. Langmuir 1999, 15:7076-7079.
48. Yoshimasa U., Takashi N. Effects of film-forming conditions on surface properties and structures of diblock copolymer with perfluoroalkyl side chains. Langmuir 2005, 21:2614-2618.
49. Takeichi T., Kawauchi T., Agag T. High performance polybenzoxazines as a novel type of phenolic resin. Polym. J. 2008, 40:1121-1131.
50. Agag T., Takeichi T. Effect of hydroxyphenylmaleimide on the curing behaviour and thermomechanical properties of rubber-modified polybenzoxazine. High Perform. Polym. 2001, 13:S327-S342.
51. Chou S.Y., Krauss P.R., Renstrom P.J. Imprint lithography with 25-nanometer resolution. Science 1996, 272:85-87.
52. Chou S.Y., Krauss P.R., Zhang W., Guo L., Zhuang L. Sub-10 nm imprint lithography and applications. J. Vac. Sci. Technol. B 1997, 15:2897-2904.
53. Chen J.K., Ko F.H., Hsieh K.F., Chou C.T., Chang F.C. Effect of fluoroalkyl substituents on the reactions of alkylchlorosilanes with mold surfaces for nanoimprint lithography. J. Vac. Sci. Technol. B 2004, 22:3233-3241.
54. Wang C.F., Chiou S.F., Ko F.H., Chen J.K., Chou C.T., Huang C.F., et al. Polybenzoxazine as a mold-release agent for nanoimprint lithography. Langmuir 2007, 23:5868-5871.
55. Gau H., Herminghaus S., Lenz P., Lipowsky R. Liquid morphologies on structured surfaces: from microchannels to microchips. Science 1999, 283:46-49.
56. Linden S., Christ A., Kuhl J., Giessen H. Selective suppression of extinction within the plasmon resonance of gold nanoparticles. Appl. Phys. B Laser Opt. 2001, 73:311-316.
57. Zhang X., Sun B., Friend R.H., Guo H., Nau D., Giessen H. Metallic photonic crystals based on solution-processible gold nanoparticles. Nano Lett. 2006, 6:651-655.
58. Fustin C.A., Glasser G., Spiess H.W., Jonas U. Site-selective growth of colloidal crystals with photonic properties on chemically patterned surfaces. Adv. Mater. 2003, 15:1025-1028.
59. Peters R.D., Yang X.M., Nealey P.F. Morphology of thin films of diblock copolymers on surfaces micropatterned with regions of different interfacial energy. Macromolecules 2002, 35:1822-1834.
60. Liao C.S., Wang C.F., Li H.C., Chou H.Y., Chang F.C. Tuning the surface free energy of polybenzoxazine thin films. J. Phys. Chem. C 2009, 112:16189-16191.
61. Macko J.A., Ishida H. Behavior of a bisphenol-A-based polybenzoxazine exposed to ultraviolet radiation. J. Polym. Sci. B Polym. Phys. 2000, 38:2687-2701.
62. Macko J.A., Ishida H. Structural effects of amines on the photooxidative degradation of polybenzoxazines. Polymer 2001, 42:6371-6383.
63. Wang R., Hashimoto K., Fujishima A., Chikuni M., Kojima E., Kitamura A., et al. Light-induced amphiphilic surfaces. Nature 1997, 388:431-432.
64. Chen W., Fadeev A.Y., Hsieh M.C., Õner D., Youngblood J., McCarthy T.J. Ultrahydrophobic and ultralyophobic surfaces: some comments and examples. Langmuir 1999, 15:3395-3399.
65. Callies M., Quere D. On water repellency. Soft Matter 2005, 1:55-61.
66. Blossey R. Self-cleaning surfaces-virtual realities. Nat. Mater. 2003, 2:301-306.
67. Lafuma A., Quéré D. Superhydrophobic states. Nat. Mater. 2003, 2:457-460.
68. Nakajima A., Fujishima A., Hashimoto K., Watanabe T. Preparation of transparent superhydrophobic boehmite and silica films by sublimation of aluminum acetylacetonate. Adv. Mater. 1999, 11:1365-1368.
69. Woodward J.T., Gwin H., Schwartz D.K. Contact angles on surfaces with mesoscopic chemical heterogeneity. Langmuir 2000, 16:2957-2961.
70. Sun T., Song W., Jiang L. Control over the responsive wettability of poly(N-isopropylacrylamide) film in a large extent by introducing an irresponsive molecule. Chem. Commun. 2005, 1723-1725.
71. Shafrin E.G., Zisman W.A. Upper limits to the contact angles of liquids on solids. Advances in Chemistry series 1964, vol. 43:145-157. American Chemical Society, Washington, DC. F.M. Fowkes (Ed.).
72. Zhang X., Shi F., Niu J., Jiang Y., Wang Z. Superhydrophobic surfaces: from structural control to functional application. J. Mater. Chem. 2008, 18:621-633.
73. Wenzel R.N. Resistance of solid surfaces to wetting by water. Ind. Eng. Chem. 1936, 28:988-994.
74. Cassie A.B.D., Baxter S. Wettability of porous surfaces. Trans. Faraday Soc. 1944, 40:546-551.
75. Neinhuis C., Barthlott W. Purity of the sacred lotus, or escape from contamination in biological surfaces. Planta 1997, 202:1-8.
76. Otten A., Herminghaus S. How plants keep dry: a physicist's point of view. Langmuir 2004, 20:2405-2408.
77. Wagner T., Neinhuis C., Barthlott W. Wettability and contaminability of insect wings as a function of their surface sculptures. Acta Zool. 1996, 3:213-225.
78. Lee W., Jin M.K., Yoo W.C., Lee J.K. Nanostructuring of a polymeric substrate with well-defined nanometer-scale topography and tailored surface wettability. Langmuir 2004, 20:7665-7669.
79. Gao X., Jiang L. Water-repellent legs of water striders. Nature 2004, 432:36.
80. Parker A.R., Lawrence C.R. Water capture by a desert beetle. Nature 2001, 414:33-34.
81. Feng L., Li S., Li Y., Li H., Zhang L., Zhai J., et al. Super-hydrophobic surfaces: from natural to artificial. Adv. Mater. 2002, 14:1857-1860.
82. Onda T., Shibuichi S., Satoh N., Tsujii K. Super-water-repellent fractal surfaces. Langmuir 1996, 12:2125-2127.
83. Morra M., Occhiello E., Garbassi F. Contact angle hysteresis in oxygen plasma treated poly(tetrafluoroethylene). Langmuir 1989, 5:872-876.
84. Woodward I., Schofield W.C.E., Roucoules V., Badyal J.P.S. Super-hydrophobic surfaces produced by plasma fluorination of polybutadiene films. Langmuir 2003, 19:3432-3438.
85. Tsujii K., Yamamoto T., Onda T., Shibuichi S. Super oil-repellent surfaces. Angew. Chem. Int. Ed. Engl. 1997, 36:1011-1012.
86. Erbil H.Y., Demirel A.L., Avci Y., Mert O. Transformation of a simple plastic into a superhydrophobic surface. Science 2003, 299:1377-1380.
87. Xie Q., Xu J., Feng L., Jiang L., Tang W., Luo X., et al. Facile creation of a super-amphiphobic coating surface with bionic microstructure. Adv. Mater. 2004, 16:302-305.
88. Lau K.K.S., Bico J., Teo K.B.K., Chhowalla M., Amaratunga G.A.J., Milne W.I., et al. Superhydrophobic carbon nanotube forests. Nano. Lett. 2003, 3:1701-1705.
89. Li H., Wang X., Song Y., Liu Y., Li Q., Jiang L., et al. Super-amphiphobic aligned carbon nanotube films. Angew. Chem. Int. Ed. 2001, 40:1743-1746.
90. Wang S., Feng L., Liu H., Sun T., Zhang X., Jiang L., et al. Manipulation of surface wettability between superhydrophobicity and superhydrophilicity on copper films. Chem. Phys. Chem. 2005, 6:1475-1478.
91. Lim H.S., Baek J.H., Park K., Shin H.S., Kim J., Cho J.H. Multifunctional hybrid fabrics with thermally stable superhydrophobicity. Adv. Mater. 2010, 22:2138-2141.
92. 4 glow plasma at low pressure, and their resulting wettability. J. Mater. Chem. 2007, 17:232-237.
93. Luo C., Zuo X., Wang L., Wang E., Song S., Wang J., et al. Flexible carbon nanotube-polymer composite films with high conductivity and superhydrophobicity made by solution process. Nano Lett. 2008, 8:4454-4458.
94. Liao K.S., Wan A., Batteas J.D., Bergbreiter D.E. Superhydrophobic surfaces formed using layer-by-layer self-assembly with aminated multiwall carbon nanotubes. Langmuir 2008, 24:4245-4253.
95. Sun T., Wang G., Liu H., Feng L., Jiang L., Zhu D. Control over the wettability of an aligned carbon nanotube film. J. Am. Chem. Soc. 2003, 125:14996-14997.
96. Huang L., Lau S.P., Yang H.Y., Leong E.S.P., Yu S.F. Stable superhydrophobic surface via carbon nanotubes coated with a ZnO thin film. J. Phys. Chem. B 2005, 109:7746-7748.
97. Liu H., Zhai J., Jiang L. Wetting and anti-wetting on aligned carbon nanotube films. Soft Matter 2006, 2:811-821.
98. Han J.T., Kim S.Y., Woo J.S., Lee G.W. Transparent, conductive, and superhydrophobic films from stabilized carbon nanotube/silane sol mixture solution. Adv. Mater. 2008, 20:3724-3727.
99. Wang C.F., Chiou S.F., Ko F.H., Chou C.T., Lin H.C., Huang C.F., et al. Fabrication of biomimetic super-amphiphobic surfaces through plasma modification of benzoxazine films. Macromol. Rapid Commun. 2006, 27:333-337.
100. Wang C.F., Wang Y.T., Tung P.H., Kuo S.W., Lin C.H., Sheen Y.C., et al. Stable superhydrophobic polybenzoxazine surfaces over a wide pH range. Langmuir 2006, 22:8289-8292.
101. Herminghaus S. Roughness-induced non-wetting. Euro. phys. Lett. 2000, 52:165-170.
102. Feng L., Yang Z., Zhai J., Song Y., Liu B., Ma Y., et al. Superhydrophobicity of nanostructured carbon films in a wide range of pH values. Angew. Chem., Int. Ed. 2003, 42:4217-4220.
103. Guo Z., Zhou F., Hao J., Liu W. Stable biomimetic super-hydrophobic engineering materials. J. Am. Chem. Soc. 2005, 127:15670-15671.
104. Zhu Y., Zhang J., Zheng Y., Huang Z., Feng L., Jiang L. Stable, superhydrophobic, and conductive polyaniline/polystyrene films for corrosive environments. Adv. Funct. Mater 2006, 16:568-574.
105. Srinivasan S., Praveen V.K., Philip R., Ajayaghosh A. Bioinspired superhydrophobic coatings of carbon nanotubes and linear systems based on the bottom-up self-assembly approach. Angew. Chem. Int. Ed. 2008, 47:5750-5754.
106. Bico J., Thiele U., Quere D. Wetting of textured surfaces. Colloids Surf. A 2002, 206:41-46.
107. Lopez G.P., Biebuyck H.A., Frisbie C.D., Whitesides G.M. Imaging of features on surfaces by condensation figures. Science 1993, 260:647-649.
108. Drelich J., Miller J.D., Kumar A., Whitesides G.M. Wetting characteristics of liquid drops at heterogeneous surfaces. Colloids Surf. A 1994, 93:1-13.
109. Tadanaga K., Morinaga J., Matsuda A., Minami T. Superhydrophobic-superhydrophilic micropatterning on flowerlike alumina coating film by the sol-gel method. Chem. Mater. 2000, 12:590-592.
110. Kim H., Kreller C.R., Tran K.A., Sisodiya V., Angelos S., Wallraff G., et al. Nanoporous thin films with hydrophilicity-contrasted patterns. Chem. Mater. 2004, 16:4267-4272.
111. Kim H.C., Wallraff G., Kreller C.R., Angelos S., Lee V.Y., Volksen W., et al. Photopatterned nanoporous media. Nano Lett. 2004, 4:1169-1174.
112. Liao C.S., Wang C.F., Lin H.C., Chou H.Y., Chang F.C. Fabrication of patterned superhydrophobic polybenzoxazine hybrid surfaces. Langmuir 2009, 25:3359-3362.
113. Gau H., Herminghaus S., Lenz P., Lipowsky R. Liquid morphologies on structured surfaces: from microchannels to microchips. Science 1999, 283:46-49.
114. Hsu C.H., Chen C., Folch A. Microcanals for micropipette access to single cells in microfluidic environments. Lab Chip 2004, 4:420-424.
115. Seemann R., Brinkmann M., Kramer E.J., Lange F.F., Lipowsky R. Wetting morphologies at microstructured surfaces. Proc. Natl. Acad. Sci. USA 2005, 102:1848-1852.