pH-sensitive fluorinated polyimides with grafted acid and base side chains

Industrial and Engineering Chemistry Research

Volumn 42, Issue 4, 2003, Pages 784-794

  Wang, W C ^a   Vora, R H ^a   Kang, E T ^a   Neoh, K G ^a   Liaw, D J ^b  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b NATIONAL TAIWAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

COPOLYMERIZATION; DIFFERENTIAL SCANNING CALORIMETRY; FOURIER TRANSFORM INFRARED SPECTROSCOPY; GRAFT COPOLYMERS; MICROFILTRATION; MONOMERS; MORPHOLOGY; ORGANIC ACIDS; OZONE; PH EFFECTS; PORE SIZE; SCANNING ELECTRON MICROSCOPY; SOLUTIONS; THERMOGRAVIMETRIC ANALYSIS;

MOLECULAR MODIFICATIONS;

POLYIMIDES;

1 METHYL 2 PYRROLIDINONE; 4 VINYLPYRIDINE; ACID; ACRYLIC ACID; ACRYLIC ACID COPOLYMER; BASE; COPOLYMER; OZONE; POLYIMIDE; POLYMER;

FLUORINATION; PH; POLYIMIDE; POLYMERIZATION;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CONCENTRATION (PARAMETERS); COULTER COUNTER; DIFFERENTIAL SCANNING CALORIMETRY; FLUORINATION; INFRARED SPECTROSCOPY; MEMBRANE FILTER; MICROFILTRATION; MORPHOLOGY; PH MEASUREMENT; POLYMERIZATION; POROSITY; SURFACE PROPERTY; THERMAL ANALYSIS; THERMOGRAVIMETRY; X RAY PHOTOELECTRON SPECTROSCOPY;

EID: 0037454085     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie020830g     Document Type: Article

References (52)

1. Wilson, A. M. Use of Polyimides in VLSI Fabrication. In Polyimides: Synthesis, Characterization, and Applications; Mittal, K. L., Ed.; Plenum: New York, 1984.
2. Wilson, D.; Stenzenberger, H. D.; Hergenrother, P. M. Polyimide; Chapman & Hall: New York, 1990.
3. Auman, B. C. Low Dielectric Constant, Low Moisture Absorption and Low Thermal Expansion Coefficient Polyimides Based on New Rigid Fluorinated Monomers. In Advances in Polyimide Science and Technology; Feger, C., Khojasteh, M. M., Htoo, M. S., Eds.; Technomic Publishing Co.: Lancaster, PA, 1993.
4. Feger, C. Selection Criteria for Multichip Module Dielectrics. In Multichip Module Technologies and Alternatives: the Basics; Doane, D. A., Franzon, P. D., Eds.; Van Nostrand Reinhold: New York, 1993; p 311.
5. Ohya, H.; Kudryavtsev, V. V.; Semenova, S. I. Polyimide Membranes: Applications, Fabrications, and Properties; Kodansha Ltd.: Kodansha, Japan, 1996.
6. Yamamoto, H.; Mi, Y.; Stern, S. A. Structure Permeability Relationships of Polyimide Membranes. J. Polym. Sci., Part B: Polym. Phys. 1990, 28, 2291.
7. Eastmond, G. C.; Gibas, M.; Pacynko, W. F.; Paprotny, J. Grafted and Segmented Hydrophilic Polyimide for Microfiltration Membranes. Part I. Synthesis and Characterization. J. Membr. Sci. 2002, 207, 29.
8. Shimizu, H.; Kawakami, H.; Nagaoka, S. Membrane Formation Mechanism and Permeation Properties of a Novel Porous Polyimide Membrane. Polym. Adv. Technol. 2002, 13, 370.
9. Niwa, M.; Kawakami, H.; Kanamori, T.; Shinbo, T.; Kaito, A.; Nagaoka, S. Gas Separation of Asymmetric 6FDA Polyimide Membrane with Oriented Surface Skin Layer. Macromolecules 2001, 34, 9039.
10. White, L. S. Transport Properties of a Polyimide Solvent Resist Nanofiltration Membrane. J. Membr. Sci. 2002, 205, 191.
11. Iwama, A.; Kazuse, Y. New Polyimide Ultrafiltration Membranes for Organic Use. J. Membr. Sci. 1982, 11, 297.
12. Gupta, A. K. S. Membranes for Oil Separation. U.S. Patent 4,533,501, 1985.
13. Peng, T.; Cheng, Y. L. Temperature-responsive Permeability of Porous PNIPAAm-g-PE Membranes. J. Appl. Polym. Sci. 1998, 70, 2133.
14. Yoshida, R.; Uchida, K.; Kaneko, Y.; Sakai, K.; Klkuchi, A.; Sakural, Y.; Okano, T. Comb-Type Grafted Hydrogels with Rapid Deswelling Response to Temperature Changes. Nature 1995, 374, 240.
15. Takei, Y. G.; Aoki, T.; Sanui, K.; Ogata, N.; Sakurai, Y.; Okano, T. Dynamic Contact Angle Measurement of Temperature-Responsive Surface Properties for Poly(N-isopropylacrylamide) Grafted Surfaces. Macromolecules 1994, 27, 6163.
16. Park, Y. S.; Ito, Y.; Imanishi, Y. Permeation Control Through Porous Membranes Immobilized with Thermosensitive Polymer. Langmuir 1998, 14, 910.
17. Jin, K. S.; Yong, B. L.; Young, M. L. pH-Dependent Permeation through Polysulfone Ultrafiltration Membranes Prepared by Ultraviolet Polymerization Technique. J. Appl. Polym. Sci. 1999, 74, 75.
18. Ju, H. K.; Kim, S. Y.; Lee, Y. M. pH/Temperature-Responsive Behaviors of Semi-IPN and Comb-type Graft Hydrogels Composed of Alginate and Poly(N-isopropylacrylamide), Polymer 2001, 42, 6851.
19. Kawasaki, H.; Sasaki, S.; Maeda, H. Effect of Introduced Electric Charge on the Volume Phase Transition of N-isopropylacrylamide Gels. J. Phys. Chem. B 1997, 101, 4184.
20. Torres-Lugo, M.; Peppas, N. A. Molecular Design and in Vitro Studies of Novel pH-Sensitive Hydrogels for the Oral Delivery of Calcitonin. Macromolecules 1999, 32, 6646.
21. Tarvainen, T.; Nevalainen, T.; Sundell, A.; Svarfvar, B.; Hyrsyla, J. Paronen, P.; Jarvinen, K. Drug Release from Poly-(acrylic acid) Grafted Poly(vinylidene fluoride) Membrane Bags in the Gastrointestinal Tract in the Rat and Dog. J. Controlled Release 2000, 66, 19.
22. Akerman, S.; Viinikka, P.; Svarfar, B.; Jarvinen, K.; Kontturi, K.; Nasman, J.; Urtti, A.; Paronen, P. Transport of Drugs Across Porous Ion Exchange Membranes. J. Controlled Release 1998, 50, 153.
23. 2 through Various Ion Exchange Membranes Prepared by Plasma Graft Polymerization. J. Membr. Sci. 1996, 117, 251.
24. Hegazy, E. A.; Abd El-Rehim, H. A.; Khalifa, N. A.; Atwa, S. M.; Shawky, H. A. Anionic/Cationic Membranes Obtained by a Radiation Grafting Method for Use in Waste Water Treatment. Polym. Int. 1997, 43, 321.
25. Roig, M. G.; Bello, J. F.; Rodriguez, S.; Kennedy, J. F.; Taylor, D. W. Phosphatase Active Cross-Flow Microfiltration Poly-(vinylidene fluoride) Bioreactor. Polym. Int. 1996, 39, 17.
26. Gerlach, J. C.; Schnoy, N.; Vienken, J.; Smith, M.; Neuhaus, P. Comparison of Hollow Fibre Membranes for Hepatocyte Immobilization in Bioreactors. Int. J. Artif. Org. 1996, 19, 610.
27. Akerman, S.; Viinikka, P.; Svarfvar, B.; Putkonen, K.; Jarvinen, K.; Kontturi, K.; Nasman, J.; Urtti, A.; Paronen, P. Drug Permeation through a Temperature-Sensitive Poly(N-isopropylacrylamide) Grafted Poly(vinylidene fluoride) Membrane. Int. J. Pharm. 1998, 164, 29.
28. Lee, Y. M.; Ihm, S. Y.; Shim, J. K.; Kim, J. H.; Cho, C. S.; Sung, Y. K. Preparation of Surface-Modified Stimuli-Responsive Polymeric Membranes by Plasma and Ultraviolet Graft Methods and Their Biboflavin Permeation. Polymer 1995, 36, 81.
29. Iwata, H.; Oodate, M.; Uyama, Y.; Amemiya, H.; Ikada, Y. Preparation of Temperature-Sensitive Membranes by Graft Polymerization onto a Porous Membrane. J. Membr. Sci. 1991, 55, 119.
30. Hester, J. F.; Banerjee, P.; Mayes, A. M. Preparation of Protein-Resistant Surfaces on Poly(vinylidene fluoride) Membranes via Surface Segregation. Macromolecules 1999, 32, 1643.
31. Nunes, S. P.; Sforca, M. L.; Peinemann, K. V. Dense Hydrophilic Composite Membranes for Ultrafiltration. J. Membr. Sci. 1995, 106, 49.
32. Vora, R. H.; Krishnan, P. S. G.; Goh, S. H.; Chung, T. S. Synthesis and Properties of Designed Low-k Fluoro-Copolyetherimides. Part 1. Adv. Funct. Mater. 2001, 11, 361.
33. Vora, R. H. Process of Making a Shaped Article from Intermediate Molecular Weight Polyimides. U.S. Patent 4,933,-132, 1990.
34. Fargere, T.; Abdennadher, M.; Delmas, M.; Boutevin, B. Synthesis of Graft Polymers from an Ozonized Ethylene-Vinyl Acetate Copolymer (EVA). 1. Study of the Radical Polymerization of Styrene Initiated by an Ozonized EVA. J. Polym. Sci., Part A: Polym. Chem. 1994, 32, 1377.
35. Strathmann, H.; Kock, K. The Formation Mechanism of Phase Inversion Membranes. Desalination 1977, 21, 241.
36. Walton, H. F. Principles & Methods of Chemical Analysis; Prentice Hall: Englewood Cliffs, NJ, 1964.
37. Boutevin, B.; Robin, J. J.; Serdani, A. Synthesis and Applications of Graft-Copolymers from Ozonized Poly(vinylidene fluoride). Eur. Polym. J. 1992, 28, 1507.
38. Fujimoto, K.; Takebayashi, Y.; Inoue, H.; Ikada, Y. Ozone-Induced Graft-Polymerization onto Polymer Surface. J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 1035.
39. Boutevin, B.; Robin, J. J.; Torres, N.; Casteil, J. Graft Copolymerization of Styrene onto Ozonized Polyethylene. Macromol. Chem. Phys. 2002, 203, 245.
40. Moharram, M. A.; Rabie, S. M.; El-Gendy, H. M. Infrared Spectra of Gamma-Irradiated Poly(acrylic acid)-Polyacrylamide Complex. J. Appl. Polym. Sci. 2002, 85, 1619.
41. Beamson, G.; Briggs, D. High-Resolution XPS of Organic Polymers: the Scienta ESCA300 Database; John Wiley: New York, 1992; p 45.
42. Zhang, Y.; Tan, K. L.; Liaw, B. Y.; Liaw, D. J.; Kang, E. T. Thermal Imidization of Poly(amic acid) Precursors on Glycidyl Methacrylate (GMA) Graft-Polymerized Si(100) Surface. Thin Solid Films 2000, 374, 70.
43. Zhang, Y.; Tan, K. L.; Yang, G. H.; Kang, E. T.; Neoh, K. G. Electroless Plating of Copper and Nickel via a Sn-free Process on Polyimide Films Modified by Surface Graft Copolymerization with 1-Vinylimidazole. J. Electrochem. Soc. 2001, 148, C574.
44. Zhou, X.; Goh, S. H.; Lee, S. Y.; Tan, K. L. X-ray Photoelectron Spectroscopic Studies of Interactions between Poly(p-vinylphenol) and Poly(vinylpyridine)s. Appl. Surf. Sci. 1997, 119, 60.
45. Ruokolainen, J.; Tanner, J.; Ikkala, O.; Brinke, G. T.; Thomas, E. L. Direct Imaging of Self-Organized Comb Copolymer-like Systems Obtained by Hydrogen Bonding: Poly(4-vinylpyridine)-4-Nonadecylphenol. Macromolecules 1998, 31, 3532.
46. Huang, X. D.; Goh, S. H.; Lee, S. Y.; Huang, C. H. A. Complexation between Hydrogensulfated Fullerenol and Poly(4-vinylpyridine). Macromol. Chem. Phys. 2000, 201, 281.
47. Ying, L.; Wang, P.; Kang, E. T.; Neoh, K. G. Synthesis and Characterization of Poly(acrylic acid)-g-Poly(vinylidene fluoride) Copolymers and pH-Sensitive Membranes. Macromolecules 2002, 35, 673.
48. Chen, N. P.; Hong, L. Surface Phase Morphology and Composition of the Casting Films of PVDF-PVP Blend. Polymer 2002, 43, 1429.
49. Kano, Y.; Akiyama, S.; Kasemura, T. Surface Enrichment in Blends of Poly(ethyl acrylate) with Poly(vinylidene fluoride-cohexafluoroacetone). Int. J. Adhes. Adhes. 1997, 17, 207.
50. Ito, Y.; Ochiai, Y.; Park, Y.; Imanishi, Y. pH-Sensitive Gating by Conformational Change of a Polypeptide Brush Grafted onto a Porous Polymer Membrane. J. Am. Chem. Soc. 1997, 119, 1619.
51. Israels, R.; Gersappe, D.; Fasolka, M.; Roberts, V. A.; Balazs, A. pH-Controlled Gating in Polymer Brushes. Macromolecules 1994, 27, 6679.
52. Liu, Y.; Goh, S. H.; Lee, S. Y.; Huan, C. Miscibility and Interactions in Blends and Complexes of Poly(N-acryloyl-N′-methylpiperazine) with Poly(p-vinylphenol). Macromolecules 1999, 32, 1967.