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Journal of Coatings Technology and Research

, Volume 17, Issue 1, pp 219–230 | Cite as

Preparation and properties of fluoroalkyl end-capped 2-acrylamido-2-methylpropanesulfonic acid oligomer/poly(vinyl alcohol) composite film

  • Shinsuke Katayama
  • Masato Yasuta
  • Hideo SawadaEmail author
Article
  • 34 Downloads

Abstract

Fluoroalkyl end-capped 2-acrylamido-2-methylpropanesulfonic acid oligomer/poly(vinyl alcohol) composite [RF-(AMPS)n-RF/PVA] films were prepared by casting homogeneous aqueous methanol solutions containing RF-(AMPS)n-RF/PVA composites, which were prepared by the reactions of the corresponding oligomer with PVA. The transparent colorless RF-(AMPS)n-RF/PVA composite films thus obtained were subjected to tensile testing to evaluate the values of Young’s modulus, tensile strength, and elongation at break. The RF-(AMPS)n-RF/PVA composites films are capable of greater Young’s modulus than the original PVA film (PVA/HCl film), which was prepared by casting the aqueous methanol solution of PVA in the presence of 1 N hydrochloric acid. The polymer film bearing a higher Young’s modulus is, in general, tough and brittle to providing lower elongation at break; however, we can observe a significant increase in both the tensile strength and elongation at break of the RF-(AMPS)n-RF/PVA composite films, compared to those of the PVA/HCl film. In addition, it was demonstrated that the RF-(AMPS)n-RF/PVA composite films can exhibit a higher water adsorption ability than that of the PVA/HCl film.

Graphic abstract

Keywords

Fluorinated oligomer Poly(vinyl alcohol) Composite film Mechanical property Composite gel Double-network gel 

Notes

Acknowledgments

This work was partially supported by a Grant-in-Aid for Scientific Research 16K05891 from the Ministry of Education, Science, Sports, and Culture, Japan.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

References

  1. 1.
    Sawada, H, “Fluorinated Peroxides.” Chem. Rev., 96 1779–1808 (1996)CrossRefGoogle Scholar
  2. 2.
    Sawada, H, “Synthesis of Self-Assembled Fluoroalkyl End-Capped Oligomeric Aggregates—Applications of These Aggregates to Fluorinated Oligomeric Nanocomposites.” Prog. Polym. Sci., 32 509–533 (2007)CrossRefGoogle Scholar
  3. 3.
    Sawada, H, “Preparation and Applications of Novel Fluoroalkyl End-Capped Oligomeric Nanocomposites.” Polym. Chem., 3 46–65 (2012)CrossRefGoogle Scholar
  4. 4.
    Sawada, H, Katayama, S, Nakamura, Y, Kawase, T, Hayakawa, Y, Baba, M, “Gelation of Fluoroalkylated 2-acrylamido-2-methylpropanesulfonic Acid Oligomers as Potential for Prevention of HIV-1 Transmission.” Polymer, 39 743–745 (1998)CrossRefGoogle Scholar
  5. 5.
    Sawada, H, Katayama, S, Ariyoshi, Y, Kawase, T, Hayakawa, Y, Tomita, T, Baba, M, “Fluorinated Functional Materials Possessing Biological Activities: Gel Formation of Novel Fluoroalkylated End-Capped 2-acrylamido-2-methylpropanesulfonic Acid Polymers Under Non-crosslinked Conditions.” J. Mater. Chem., 8 1517–1524 (1998)CrossRefGoogle Scholar
  6. 6.
    Sawada, H, Nakamura, Y, Katayama, S, Kawase, T, “Gelation of Fluoroalkylated End-Capped Oligomers Containing Triol Segments under Non-Crosslinked Conditions, and Binding or Releasing of Metal Ions by These Oligomers.” Bull. Chem. Soc. Jpn., 70 2839–2845 (1997)CrossRefGoogle Scholar
  7. 7.
    Sawada, H, Tanimura, T, Katayama, S, Kawase, T, “Aggregation of Fluoroalkyl Units: Synthesis of Gelling Fluoroalkylated End-Capped Oligomers Containing Hydroxy Segments Possessing Metal Ion Binding and Releasing Abilities.” Chem. Commun., 15 1391–1392 (1997)CrossRefGoogle Scholar
  8. 8.
    Sawada, H, Tanimura, T, Katayama, S, Kawase, T, Tomita, T, Baba, M, “Synthesis and Properties of Gelling Fluoroalkylated End-Capped Oligomers Containing Hydroxy Segments.” Polym. J., 30 797–804 (1998)CrossRefGoogle Scholar
  9. 9.
    Sawada, H, Shima, K, Kyokane, J, Oharu, K, Nakagawa, H, Kitazume, T, “Gelation and Ionic Conductivity of Fluoroalkyl End-Capped 2-acrylamido-2-methylpropanesulfonic Acid Oligomers in Ionic Liquids.” Eur. Polym. J., 40 1595–1597 (2004)CrossRefGoogle Scholar
  10. 10.
    Sawada, H, Ariyoshi, Y, Lee, K, Kyokane, J, Kawase, T, “A New Approach to Highly Conductive Polymer Electrolytes: Synthesis of Gelling Fluoroalkylated End-Capped 2-acrylamido-2-methylpropanesulfonic Acid Copolymers Containing Poly(oxyethylene) Units.” Eur. Polym. J., 36 2523–2526 (2000)CrossRefGoogle Scholar
  11. 11.
    Wang, J, Wang, X, Xu, C, Zhang, M, Shang, X, “Preparation of Graphene/Poly(vinyl alcohol) Nanocomposites with Enhanced Mechanical Properties and Water Resistance.” Polym. Int., 60 816–822 (2011)CrossRefGoogle Scholar
  12. 12.
    Huang, RYM, Rhim, JW, “Modification of Poly(vinyl alcohol) Using Maleic Acid and its Application to the Separation of Acetic Acid‐Water Mixtures by the Pervaporation Technique.” Polym. Int., 30 129–137 (1993)CrossRefGoogle Scholar
  13. 13.
    Yeom, CK, Huang, RYM, “Development of Crosslinked Poly(vinyl alcohol) (type II) and Permeation of Acetic Acid—Water Mixtures.” Angew. Makromol. Chem., 184 27–35 (1991)CrossRefGoogle Scholar
  14. 14.
    Yeom, CK, Lee, KH, “Pervaporation Separation of Water-Acetic Acid Mixtures Through Poly(vinyl alcohol) Membranes Crosslinked with Glutaraldehyde.” J. Membr. Sci., 109 257–265 (1996)CrossRefGoogle Scholar
  15. 15.
    Rhin, JW, Yoon, SW, Kim, SW, Lee, KH, “Pervaporation Separation and Swelling Measurement of Acetic Acid–Water Mixtures Using Crosslinked PVA Membranes.” J. Appl. Polym. Sci., 63 521–527 (1997)CrossRefGoogle Scholar
  16. 16.
    Bandyopadhyay, A, DE Sarkar, M, Bhowmick, AK, “Poly(vinyl Alcohol)/silica Hybrid Nanocomposites by Sol-Gel Technique: Synthesis and Properties.” J. Mater. Sci., 40 5233–5241 (2005)CrossRefGoogle Scholar
  17. 17.
    Uragami, T, Okazaki, K, Matsugi, H, Miyata, T, “Structure and Permeation Characteristics of an Aqueous Ethanol Solution of Organic−Inorganic Hybrid Membranes Composed of Poly(vinyl alcohol) and Tetraethoxysilane.” Macromolecules, 35 9156–9163 (2002)CrossRefGoogle Scholar
  18. 18.
    Hu, WW, Zhang, HH, Zhang, QG, Liu, QL, Zhu, AM, “Pervaporation Dehydration of Water/Ethanol/Ethyl Acetate Mixtures Using Poly(vinyl alcohol)-Silica Hybrid Membranes.” J. Appl. Polym. Sci., 126 778–787 (2012)CrossRefGoogle Scholar
  19. 19.
    Zheng, QG, Liu, QL, Zhu, AM, Xiong, Y, Zhang, XH, “Characterization and Permeation Performance of Novel Organic−Inorganic Hybrid Membranes of Poly(vinyl alcohol)/1,2-Bis(triethoxysilyl)ethane.” J. Phys. Chem. B, 112 16559–16565 (2008)CrossRefGoogle Scholar
  20. 20.
    Aomi, Y, Sawada, H, “Preparation of Amphiphobically Modified Poly(vinyl alcohol) Film by Fluoroalkyl End-Capped Vinyltrimethoxysilane Oligomer.” J. Coat. Technol. Res., (2019).  https://doi.org/10.1007/s11998-018-0148-2 CrossRefGoogle Scholar
  21. 21.
    Stammen, JA, Williams, S, Ku, DN, Guldberg, RE, “Mechanical Properties of a Novel PVA Hydrogel in Shear and Unconfined Compression.” Biomaterials, 22 799–806 (2001)CrossRefGoogle Scholar
  22. 22.
    Anseth, KS, Bowman, CN, Brannon-Peppas, L, “Mechanical Properties of Hydrogels and Their Experimental Determination.” Biomaterials, 17 1647–1657 (1996)CrossRefGoogle Scholar
  23. 23.
    Gu, Z-Q, Xiao, J-M, Zhang, X-H, “The Development of Artificial Articular Cartilage—PVA‐Hydrogel.” Biomed. Mater. Eng., 8 75–81 (1998)Google Scholar
  24. 24.
    Gong, JP, Katsuyama, Y, Kurokawa, T, Osada, Y, “Double–Network Hydrogels with Extremely High Mechanical Strength.” Adv. Mater., 15 1155–1158 (2003)CrossRefGoogle Scholar
  25. 25.
    Gong, JP, Kurokawa, T, Narita, T, Kagata, G, Osada, Y, Nishimura, G, Kinjo, M, “Synthesis of Hydrogels with Extremely Low Surface Friction.” J. Am. Chem. Soc., 123 5582–5583 (2001)CrossRefGoogle Scholar
  26. 26.
    Hanabusa, K, Tanaka, R, Suzuki, M, Kimura, M, Shirai, H, “Excellent Gelators for Organic Fluids: Simple Bolaform Amides Derived from Amino Acids.” Adv. Mater., 9 1095–1097 (1997)CrossRefGoogle Scholar
  27. 27.
    Hanabusa, K, Okui, K, Karaki, K, Kimura, M, Shirai, H, “Organogels Formed by N-Benzyloxycarbonyl-l-alanine 4-Hexadecanoyl-2-nitrophenyl Ester and Related Compounds.” J. Colloid Interface Sci., 195 86–93 (1997)CrossRefGoogle Scholar
  28. 28.
    Sakurada, I, Matsuzawa, S, “Crosslinking of Poly (Vinylalcohol) by Treatment with Hydrochloric Acid.” Kobunshi Kagaku, 20 353–356 (1963).  https://doi.org/10.1295/koron1944.20.353 CrossRefGoogle Scholar
  29. 29.
    Kijima, T, Nishida, M, Fukaya, H, Yoshida, M, Sawada, H, “Coloring–Decoloring Behavior of Fluoroalkyl End-Capped 2-Acrylamido-2-methylpropanesulfonic Acid Oligomer/Acetone Composite in Methanol.” J. Polym. Sci. Part A: Polym. Chem., 51 2555–2564 (2013)CrossRefGoogle Scholar
  30. 30.
    Suekama, T, Hu, J, Kurokawa, T, Gong, JP, Gehrke, SH, “Tuning Mechanical Properties of Chondroitin Sulfate‐Based Double‐Network Hydrogels.” Macromol. Symp., 329 9–18 (2013)CrossRefGoogle Scholar
  31. 31.
    Fujiwara, M, Ashida, N, Okamoto, M, Mizuta, T, Ide, T, Hanasaki, Y, Katsuura, K, Sawada, H, Shigeta, S, Konno, K, Yokota, T, Baba, M, “RD6-2198, a Novel Betain-Type Fluoroalkylated Oligomer, Inhibits the Replications of Human Immunodeficiency Virus Type 1 and Other Enveloped Viruses.” Antivir. Res., 38 141–149 (1998)CrossRefGoogle Scholar

Copyright information

© American Coatings Association 2019

Authors and Affiliations

  • Shinsuke Katayama
    • 1
    • 2
  • Masato Yasuta
    • 1
  • Hideo Sawada
    • 1
    Email author
  1. 1.Department of Frontier Materials Chemistry, Graduate School of Science and TechnologyHirosaki UniversityHirosakiJapan
  2. 2.Production Engineering DepartmentKanto Denka Kogyo Co., Ltd.KurashikiJapan

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