Synhtesis of Novel Surface Active Methacrylate Monomers Based on ε-Caprolactone
Affiliation:
Lviv Polytechnic National University
12, Bandera str., 79013 Lviv, Ukraine; nickborzenkov@gmail.com
DOI:
https://doi.org/10.23939/chcht08.02.141
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Abstract:
The interaction of ε-caprolactone with methacrylic acid has resulted in formation of 6-methacryloylhexanoate which was subsequently converted into the corresponding chloroanhydride via the reaction with phosphorus trichloride. The reaction of chloroanhydride with poly(ethylene glycol) or poly(ethylene glycol) monomethyl ether yielded the corresponding surface active methacrylate monomers. During interaction of the hydroxyl group of poly(ethylene glycol) containing the monomer with the excess of phosphoryl chloride phosphate-containing monomer was synthesized. The synthesized monomers exhibit surfactant properties and reduce the surface tension at the aqueous solution – air interface.
References:
[1] Mekkil S., Saidi-Besbes S., Elaisarri A. and Valour J.: Macromolecular Symposia, 2010, 286, 100.
https://doi.org/10.1002/masy.201051015
[2] Volkov V. and Rodionova R.: Fibre Chemistry, 2006, 38, 359.
https://doi.org/10.1007/s10692-006-0090-4
[3] Capek I.: Adv. Colloid Interface Sci., 2000, 88, 295.
https://doi.org/10.1016/S0001-8686(99)00025-1
[4] Nagai K.: Trends Polym. Sci., 1996, 4, 122.
[5] Hevus O., Kohut A., Fleychuk R. et al.: Macromolecular Symposia, 2007, 254, 117.
https://doi.org/10.1002/masy.200750818
[6] Yoshimura T., Koide Y., Shosenji H. and Esumi K.: J. Surfactants and Detergents, 2002, 5, 257.
https://doi.org/10.1007/s11743-002-0225-x
[7] Nilson K., Mellin L., Nederberg F. and Bowden T.: Macromolecules, 2007, 40, 901.
https://doi.org/10.1021/ma0605696
[8] Yang S., Xiong P., Gong T. et al.: Eur. Polymer J., 2005, 41, 2973.
https://doi.org/10.1016/j.eurpolymj.2005.06.017
[9] Borzenkov M., Dolynska L., Kochubei V., et al.: Chem & Chem. Techn., 2011, 5, 363.
[11] Cho H.: J. Appl. Polym. Sci., 2010, 116, 736.
https://doi.org/10.1002/app.30211
[12] Li W. and Matjaszewski K.: Macromolecules, 2011, 44, 5578.
https://doi.org/10.1021/ma201058t
[13] Klee E. and Lehmann U.: Beilstein J. Org. Chem., 2010, 6, 766.
https://doi.org/10.3762/bjoc.6.95
[14] Anada K., Nacharaju P., Smith P. et al.: Anal. Biochem., 2008, 374, 231.
https://doi.org/10.1016/j.ab.2007.11.034
[15] Scott M., Convertine A. and Danielle S.: Bioconjugate Chem., 2009, 20, 1122.
https://doi.org/10.1021/bc800426d
[16] Soula O., Gyout A. and Williams N.: J. Polym. Sci. A, 1993, 37, 4202.
[17] Narain R., Jhurry D. and Wulf G.: Eur. Polym. J., 2002, 38, 273.
https://doi.org/10.1016/S0014-3057(01)00172-0
[18] Senhaji O., Robin J., Achchoubi M. and Boutevin B.: Macromolecular Chemistry and Physics, 2004, 205, 1039.
https://doi.org/10.1002/macp.200400011
[19] Jaeger W., Bohrisch J. and Laschewsky A.: Progr. in Polymer Sci., 2010, 35, 511.
https://doi.org/10.1016/j.progpolymsci.2010.01.002
[20] Prabhakaran M., Manjula B. and Acharya S.: Artificial Cells, Blood Substitutes and Immobilization Biotechn., 2006, 34, 381.
https://doi.org/10.1080/10731190600769164
[21] Liechty W., Kryscio D., Slaughter B. and Peppas N.: Annual Rev. Chem. and Biomolecular Eng., 2010, 1, 149.
https://doi.org/10.1146/annurev-chembioeng-073009-100847
[22] Hunter A. and Moghimi S.: Biochimica et Biophysica Acta, 2010, 1797, 1203.
[23] Srinivas R., Sanjoy S. and Chaudhuri A.: Chem. Soc. Rev., 2009, 38, 3326.
https://doi.org/10.1039/b813869a
[24] Markovsky E. et al.: J. of Controlled Release, 2012, 161, 446.
https://doi.org/10.1016/j.jconrel.2011.12.021
[25] Kory M., Kristi L. and Millicent O.: Langmuir, 2011, 27, 2739.
https://doi.org/10.1021/la104313z
[26] Convertine A. et al.: Biomacromolecules, 2010, 11, 2904.
https://doi.org/10.1021/bm100652w
[27] Johnson R. et al.: Adv. Funct. Mat., 2012, 22, 1058.
https://doi.org/10.1002/adfm.201102756
[28] Kapoor Y. and Chauhan A.: Int. J. Pharm., 2008, 361, 222.
https://doi.org/10.1016/j.ijpharm.2008.05.028
[29] Aguilar M. et al.: Topics in Tissue Engineering, 2007, 3, Chapter 6.
[30] Zobel H. et al.: Eur. J. of Pharmaceutics and Biopharmaceutics, 1999, 47, 203.
https://doi.org/10.1016/S0939-6411(98)00100-3
[31] Zaicev S.: Supramolekuliarnue Sistemy na Granice razdela faz kak Modeli Biomembran i Nanomaterialy. Nord Computer, Moskwa 2006.
[32] Buler K. and Pirson D.: Organiceskie Sintezy. Mir, Moskwa 1973.
[33] Zhou Y. et al.: Materials, 2009, 2, 636.
https://doi.org/10.3390/ma2020636
[34] Perez E. et al.: J. of Bioactive and Compatible Polymers, 2013, 28, 50.
https://doi.org/10.1177/0883911512469710
[35] Koleske J.: Radiation Curing of Coatings, ASTM International, Bridgeport 2002.
https://doi.org/10.1520/MNL45-EB
[36] Jorge I. et al.: J. Mat. Sci.: Mat. in Medicine, 2012, 23, 1605.
[37] Bury K., Neugebauer D. and Biela T.: Reactive and Functional Polymers, 2011, 71, 616.
https://doi.org/10.1016/j.reactfunctpolym.2011.02.009
[38] Wenlong Z. et al.: Biomacromolecules, 2010, 11, 1331.
https://doi.org/10.1021/bm100116g
[39] Vaisberg A. and Proskauer E.: Organiceskie Rastvoriteli. Inost. literatura, Moskwa 1958.
[40] Cheroniks N. and Ma T.: Micro-i Polumicrometodu Organiceskogo Funkcuonalnogo Analiza. Khimiya, Moskwa 1973.
[41] Abramzon A. and Zaichenko L.: Poverchnostno-Aktivnye Veshestva. Sintez, Analiz, Svoistva i Priminenie. Khimiya, Leningrad 1988.
[42] Potapov V. and Ponomarev S.: Organicum. Prakticum po Organiceskoi Khimii. Mir, Moskwa 1979.
[43] Kohut A., Hevus O. and Voronov S.: Conf. "Polymers of Special Applications", Poland, Radom 2002, 152.
[44] Sato T. et al.: J. Appl. Polym. Sci., 2005, 98, 731.
https://doi.org/10.1002/app.22080
[45] Ko Y. and Ma P.: J. Colloid Interface Sci., 2009, 330, 77.
https://doi.org/10.1016/j.jcis.2008.10.015
[46] Raj P. and Dentino A.: Clinical, Cosmetic and Investigational Dentistry, 2001, 3, 25.
https://doi.org/10.2147/CCIDE.S16860
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