Preparation and Characterization of Environmental Functional Poly(Styrene-Co-2-[(Diethylamino)Methyl]- 4-Formyl-6-Methoxy-Phenyl Acrylate) Copolymers for Amino Acid Post Polymerization
Vanillin was used as renewable resource for preparing new monomer in two stops. The monomer has tertiary amine group which facilitates the pH change and functional aldehyde group that encourages the formation of Schiff base. It was abbreviated by DEAMVA and evaluated using chemical analysis e.g. 1H NMR, 13C NMR and FT IR all data were in logic case. Copolymerization of Styrene with 5 and 15 mol% of DEAMVA has been done by free radical polymerization and AIBN as initiator. The copolymers have been chemically and physically characterized e.g. 1H NMR, FT IR, GPC, and DSC. Post polymerization of poly (styrene-Co-DEAMVA) with 15 mol% (III b) was prepared for immobilization of tryptophan and investigated by the same methods used lately. Moreover, the sensitivity of the posted copolymer to pH has also studied by UV-vis. Spectroscopy. Scanning electron microscopy (SEM) was used to study the morphological feature of polymer surface after immobilization of tryptophan.
References
[1]
Young, J.K. and Yukiko, T.M. (2017) Thermo-Responsive Polymers and Their Application as Smart Biomaterials. Journal of Materials Chemistry B, 5, 4307-4321.
https://doi.org/10.1039/C7TB00157F
[2]
Abdelaty, M.S.A. and Kuckling, D. (2016) Synthesis and Characterization of New Functional Photo Cross-Linkable Smart Polymers Containing Vanillin Derivatives. Gels, 2, 1-13. https://doi.org/10.3390/gels2010003
[3]
Sato, E., Masuda, Y., Kadota, J., Nishiyama, T. and Horibe, H. (2015) Dual Stimuli-Responsive Homopolymers: Thermo- and Photo-Responsive Properties of Coumarin-Containing Polymers in Organic Solvents. European Polymer Journal, 69, 605-615. https://doi.org/10.1016/j.eurpolymj.2015.05.010
[4]
Chen, J.-K. and Chang, C.-J. (2014) Fabrication and Applications of Stimuli-Responsive Polymer Films and Patterns on Surface. Materials, 7, 805-875.
https://doi.org/10.3390/ma7020805
[5]
Tao, Y.C., Liu, S.W., Zhang, Y., Chi, Z.G. and Xu, J.R. (2018) A pH-Responsive Polymer Based on Dynamic Imine Bonds as a Drug Delivery Material with Pseudo Target Release Behaviour. Polymer Chemistry, 9, 878-884.
https://doi.org/10.1039/C7PY02108A
[6]
Eiji, Y., Orc, I., Tomohiro, O., Misato, O., Shinjae, P., Atsushi, H., Masamichi, Y., Kazuo, A., Takeshi, T., Norihiko, I., Tomohiro, I. and Yoshiharu, O. (2018) Bleomycin-Loaded pH-Sensitive Polymer-Lipid-Incorporated Liposomes for Cancer Chemotherapy. Polymers, 10, 74.
[7]
Kocak, G., Tuncer, C. and Bütün, V. (2017) pH-Responsive Polymers. Polymer Chemistry, 8, 144-176. https://doi.org/10.1039/C6PY01872F
[8]
Bazban-Shotorbani, S., Hasani-Sadrabadi, M., Karkhaneh, A., Serpooshan, V., Jacob, K.I., Moshaverinia, A. and Mahmoudi, M. (2017) Revisiting Structure-Property Relationship of pH-Responsive Polymers for Drug Delivery Applications. Journal of Controlled Release, 253, 46-63. https://doi.org/10.1016/j.jconrel.2017.02.021
[9]
Ankit, K., Carlo, M. and Hyo-Jick, C. (2017) Smart Microparticles with a pH-Responsive Macropore for Targeted Oral Drug Delivery. Scientific Reports, 7, 3059-3067.
https://doi.org/10.1038/s41598-017-03259-x
[10]
Liu, L., Yao, W.D., Rao, Y.F., Lu, X.Y. and Gao, J.Q. (2017) pH-Responsive Carriers for Oral Drug Delivery: Challenges and Opportunities of Current Platforms. Drug Delivery, 24, 569-581. https://doi.org/10.1080/10717544.2017.1279238
[11]
Jing, X., Anqi, L. and Jianshu, L. (2017) Advances in pH-Sensitive Polymers for Smart Insulin Delivery. Macromolecular Rapid Communications, 38, Article ID: 1700413.
[12]
Chen, G. and Hoffman, A.S. (1995) Graft Copolymers That Exhibit Temperature-Induced Phase Transition over a Wide Range of pH. Nature, 373, 49-52.
https://doi.org/10.1038/373049a0
[13]
Hoffman, A.S., Stayton, P.S. and Bulmus, V. (2000) Really Smart Bioconjugates of Smart Polymers and Receptor Proteins. Journal of Biomedical Materials Research, 52, 577-586.
https://doi.org/10.1002/1097-4636(20001215)52:4<577::AID-JBM1>3.0.CO;2-5
[14]
Costa, E., Coelho, M., Ilharco, L.M., Aguiar-Ricardo, A. and Hammond, P.T. (2011) Tannic Acid Mediated Suppression of PNIPAM Microgels Thermoresponsive Behaviour. Macromolecules, 44, 612-621. https://doi.org/10.1021/ma1025016
[15]
Yang, H.W., Chena, J.K., Cheng, C.C. and Kuo, S.W. (2013) Association of Poly(N-isopropylacrylamide) Containing Nucleobase Multiple Hydrogen Bonding of Adenine for DNA Recognition. Applied Surface Science, 271, 60-69.
https://doi.org/10.1016/j.apsusc.2013.01.074
[16]
Fache, M., Darroman, E., Besse, V., Auvergne, R., Sylvain Caillol, S. and Boutevina, B. (2014) Vanillin, a Promising Biobased Building-Block for Monomer Synthesis. Green Chemistry, 16, 1987-1998. https://doi.org/10.1039/C3GC42613K
[17]
Ananda, S.A., Bernard, W. and Ashfaqur, R. (2012) Vanillin Based Polymers: I. An Electrochemical Route to Polyvanillin. Green Chemistry, 14, 2395-2397.
https://doi.org/10.1039/c2gc35645g
[18]
Ananda, S.A. and Ashfaqur, R. (2012) Vanillin-Based Polymers-Part II: Synthesis of Schiff Base Polymers of Divanillin and Their Chelation with Metal Ions. Polymer Science, 1, 1-5.
[19]
Mohammed, I.A. and Hamidi, R.M. (2012) Synthesis of New Liquid Crystalline Diglycidyl Ethers. Molecules, 17, 645-656. https://doi.org/10.3390/molecules17010645
[20]
Ahmed, M.K., Reham, A.A., Osama, M.D., Ahmed, I.H., Afaf, A.N. and Samira, T. (2017) Synthesis, Characterization, and Evaluation of Antimicrobial Activities of Chitosan and Carboxymethyl Chitosan Schiff-Base/Silver Nanoparticles. Journal of Chemistry, 2017, Article ID: 1434320.
[21]
Firdaus, M. and Meier, M.A.R. (2013) Renewable Copolymers Derived from Vanillin and Fatty Acid Derivatives. European Polymer Journal, 49, 156-166.
https://doi.org/10.1016/j.eurpolymj.2012.10.017
[22]
MialonLVanderhenst, R., Pemba, A.G. and Miller, S.A. (2011) Polyalkylenehydroxybenzoates (PAHBs): Biorenewable Aromatic/Aliphatic Polyesters from Lignin. Macromolecular Rapid Communications, 32, 1386-1392.
https://doi.org/10.1002/marc.201100242
[23]
Srinivasa Rao, V. and Samui, A.B. (2008) Molecular Engineering of Photoactive Liquid Crystalline Polyester Epoxies Containing Benzylidene Moiety. Polymer Chemistry, 46, 7637-7655. https://doi.org/10.1002/pola.23064
[24]
Sini, N.K., Bijwe, J. and Varma, I.K. (2014) Renewable Benzoxazine Monomer from Vanillin: Synthesis, Characterization, and Studies on Curing Behaviour. Journal of Polymer Science Part A: Polymer Chemistry, 52, 7-11.
https://doi.org/10.1002/pola.26981
[25]
Shimasaki, T., Yoshihara, S. and Shibata, M. (2012) Preparation and Properties of Biocomposites Composed of Sorbitol-Based Epoxy Resin, Pyrogallol-Vanillin Calixarene, and Wood Floor. Polymer Composites, 33, 1840-1847.
https://doi.org/10.1002/pc.22327
[26]
Xin, Y. and Yuan, J. (2012) Schiff’s Base as a Stimuli-Responsive Linker in Polymer Chemistry. Polymer Chemistry, 3, 3045-3055. https://doi.org/10.1039/c2py20290e
[27]
Zhou, L., Cai, Z., Yuan, J., Kang, Y., Yuan, W. and Shen, D. (2011) Multifunctional Hybrid Magnetite Nanoparticles with pH-Responsivity, Superparamagnetism and Fluorescence. Polymer International, 60, 1303-1308.
[28]
Lyas, G., Burak, A., Serkan, K., Oguz, Y.S., Emel, Y. and Selahattin, S. (2017) Synthesis of Imine Bond Containing Insoluble Polymeric Ligand and Its Transition Metal Complexes, Structural Characterization and Catalytic Activity on Esterification Reaction. Designed Monomers and Polymers, 1, 441-448.
[29]
Etika, K.C., Cox, M.A. and Grunlan, J.C. (2010) Tailored Dispersion of Carbon Nanotubes in Water with pH-Responsive Polymers. Polymer, 51, 1761-1770.
https://doi.org/10.1016/j.polymer.2010.02.024
[30]
Oda, Y., Kanaoka, S. and Aoshima, S. (2010) Synthesis of Dual pH/Temperature-Responsive Polymers with Amino Groups by Living Cationic Polymerization. Journal of Polymer Science Part A: Polymer Chemistry, 48, 1207-1213.
https://doi.org/10.1002/pola.23882
[31]
Yan, Q., Zhou, R., Fu, C., Zhang, H., Yin, Y. and Yuan, J. (2011) CO2-Responsive Polymeric Vesicles That Breathe. Angewandte Chemie International Edition, 50, 4923. https://doi.org/10.1002/anie.201100708
[32]
Dondoni, A. and Marra, A. (2012) Recent Applications of Thiolene Coupling as a Click Process for Glycoconjugation. Chemical Society Reviews, 41, 573-586.
https://doi.org/10.1039/C1CS15157F
[33]
Fu, R. and Fu, G. (2011) Polymeric Nanomaterials from Combined Click Chemistry and Controlled Radical Polymerization. Polymer Chemistry, 2, 465-475.
https://doi.org/10.1039/C0PY00174K
[34]
Franc, G. and Kakkar, A.K. (2010) Click Methodologies: Efficient, Simple and Greener Routes to Design Dendrimers. Chemical Society Reviews, 39, 1536-1544.
https://doi.org/10.1039/b913281n
[35]
Iha, R.K., Wooley, K.L., Nyström, A.M., Burke, D.J., Kade, M.J. and Hawker, C.J. (2009) Applications of Orthogonal “Click” Chemistries in the Synthesis of Functional Soft Materials. Chemical Reviews, 109, 5620-5686.
https://doi.org/10.1021/cr900138t
[36]
Gupta, S., Kuckling, D., kretschmer, K., Choudhary, V. and Adler, H.J. (2007) Synthesis and Characterization of Stimuli-Sensative Micro- and Nanohydrogel Based on Photocrosslinkable Poly(Dimethylaminoethyl Methscrylate). Journal of Polymer Science Part A: Polymer Chemistry, 45, 669-679. https://doi.org/10.1002/pola.21846
[37]
Mark, J.E. (2009) Polymer Data Handbook. 2nd Edition, Oxford University Press, Oxford.
