Abstract
A series of acrylic terpolymers containing silyl pendant groups was prepared by free radical cross-linking copolymerization. Me3Si, Et3Si and t-BuMe2Si together with cubane-1, 4-dicarboxylic acid (CDA) were covalently linked with 2-hydroxyethyl methacrylate (HEMA). The silyl-linked HEMA are abbreviated as TMSiEMA, TESiEMA and TBSiEMA respectively. Cubane-1, 4-dicarboxylic acid (CDA) linked to two HEMA group is the cross-linking agent (CA). Free radical cross-linking terpolymerization of the methyl methacrylate (MMA) and methacrylic acid (MAA) with two different molar ratios of organosilyl monomers and CA was carried out at 60–70 ∘C. The compositions of the cross-linked three-dimensional polymers were determined by FT-IR spectroscopy. The glass transition temperature (Tg) of the network polymers was determined calorimetrically. The Tg of network terpolymers increases with increasing of cross-linking degree. Equilibrium swelling studies were carried out in enzyme-free simulated gastric and intestinal fluids (SGF and SIF, respectively). The gels swelled more in SIF than in SGF. The swelling behaviour of the copolymers was dependent on the content of MAA groups and caused a decrease in gel swelling in pH 1 or an increase in gel swelling in pH 7.4. Based on the great difference in swelling ratio at pH 1 and 7.4 for P-1, P-6 and P-10 appear to be good candidates for colon-specific drug delivery.
Similar content being viewed by others
References
Harris, F.W., Controlled release from polymers containing pendent bioactive substituents, in Medical Application of Controlled Release, R.S. Langer, D.L. Wise, (Eds.), CRC Press, Boca Raton, FL, 1984.
Martin, B.D., Linhardt, R.J. & Dordick, J.S., 1998 Highly swelling hydrogels from ordered galactose-based polyacrylates. Biomaterials 19, 69–76.
Cicek, H. & Tuncel, A. 1998 Immobilization of α-chymotrypsin in thermally reversible isopropyl acrylamide-hydroxyethyl methacrylate copolymer gel. J. Polym. Sci., Part A Polym. Chem 36, 543–552.
Jayakumar, R., Balaji, R., & Nanjundan, S. 2000 Studies on copolymers of 2-(N-phthalimido) ethyl methacrylate with methyl methacrylate. Eur Polym J. 36(8), 1659– 1666.
Madheswari, D. & Nanzundan, S. 1992 Copolymers of p-biphenyl acrylate with methyl methacrylate: synthesis, characterization and monomer reactivity ratios. Eur Polym J 28(9), 1123–1126.
Joshi, H.N. 1988, Recent advances in drug delivery systems. Polymeric prodrugs, Pharm. Technol. 12, 112.
Langer, R.S. & Peppas, N. A. 1981 Present and future applications of biomaterials in controlled drug delivery system. Biomaterials 2, 201–214.
Nakadaira, Y. Ohara, K. & Sakurai, H. 1986 Chemistry of organosilicon compounds: sterically crowded silanes. J Organomet Chem 309, 247–256.
Yampolskii, Y., Pavlova, A., Ushakov, N. & Finkelshtein, E. 1994 On the unusually high solubility of a trimethylsilyl derivative of poly (dimethylsilacyclobutane). Macromol Rapid Commun 15(12), 917–922.
Finkelshtein, E., Makoveskii, K., Yampolskii, Y., Ostrovskaya, I., Portnykh, E. & Kalyuhnyi, N. et al. 1991 Ring opening metathesis polymerization of norbornenes with organosilicon substituents. Gas permeability of polymers obtained. Makromol Chem 192(1), 1–9.
Kim, Y., Kwon, S. & Choi, S. 1997 Synthesis and properties of poly (1, 6-heptadiyne) having a bulky siloxy group. Macromolecules 30(21), 6677–6679.
Safa, K., Babazadeh, M., Namazi, H., Mahkam, M. & Assadi, G. 2004 Synthesis and characterization of new polymer systems containing very bulky tris(trimethylsilyl) methyl substituents as side chains. Eur Polym J 40, 459– 466.
Neilson, P.W. 1996 Gas permeation studies of silylated derivatives of poly (methylphenylphosphazene). Macromolecules 29(10), 3457–3461.
Zhang, J. & Hou, X. 1994 The gas permeation property in trimethylsilyl-substituted PPO and triphenylsilyl-substituted PPO. J Membr Sci 97, 257–282.
Montheard, J.P., Jegat, C. & Camps, M. 1999 Vinylbenzylchloride (chloromethylstyrene), polymers, and copolymers: recent reactions and applications. J Macromol Sci Polym Rev 39(1), 135–174.
Kowalewska, A., Stanczyk, W.A., Boileau, S., Letel, L., & Smith, J.D. 1999 Novel polymer systems with very bulky organosilicon side chain substituents. Polymer 40, 813.
Park, K.Y., Kim, H.J., Kim, W.Y., Jeong, Y.S. & Lee, Y.S. 2001 Polymer membranes containing 4-trimethylsilylmethylstyrene units. Bull. Korean. Chem. Soc. 22, 1049–1052.
Nagasaki, Y., Suda, M., & Tsuruta, T. 1989 Poly [4-bis (trimethylsilyl) methylstyrene] for an oxygen-permeable membrane. Macromol. Chem., Rapid Commun. 10, 255–258.
Nagasaki, Y. & Tsuruta, T. 1986 A novel synthesis of styrene derivatives with silylmethyl groups. Macromol. Chem., Rapid Commun. 7, 437–442.
Mahkam, M., sharifi, N., & Entezami, A.A. 2000 Regulation of controlled release of Ibuprofen from cross-linked polymer containing Cubane as a new cross-linking agent. J. Bioact. Comp. Polym 15, 396–405.
Mahkam, M. 2004 Controlled release of biomolecules from pH-sensitive hydrogels prepared by radiation polymerization. J. Bioact. Comp. Polym. 19(3), 209–220.
Mahkam, M., Assadi, M.G., zahedifar, R., Ramesh, M. & Davaran, S. 2004 Linear type azo-containing polyurethanes for colon specific drug delivery. J. Bioact. Comp. Polym. 19, 45–53.
Chung, K.T., Flunk, G.E. & Egan, M. 1976 Azo dye reduction by anaerobes. Appl. Environ. Microbiol. 5, 558.
Schroeder, H. & Campbell, D.E. 1972 Absorption, metabolism and excretion of salicylazosulfopyridine in man. Clin. Pharmacol. Ther. 13, 539.
Chourasia, M.K. & Jain, S.K. 2003 Pharmaceutical approaches to colon targeted drugs delivery systems. J. Pharm. Pharma. Sci. 6(1): 33–66.
Moreau, J.C., et al. 1991 Journal of Materials Science: Materials in Medicine 2, 243–247.
Hsieh, D.S.T., Chiang, C.C., & Desai, D.S. 1985 Pharmaceutical Technology 39–49.
Kajihara, M., et al. 2003 Chemical and Pharmaceutical Bulletin 51, 11–14.
Pfister, W.R., Sweet, R.P., Weaver, M.E. & Walters, P.A. 1985 Proceedings of the International Symposium on Controlled Release of Bioactive Materials 12, 145.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Mahkam, M., Mohammadi, R., Assadi, M.G. et al. Synthesis and characterization of new cross-linked terpolymer systems containing silyl group. Silicon Chem 3, 51–58 (2006). https://doi.org/10.1007/s11201-005-9001-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11201-005-9001-4