A Novel Strategy for Poly(β-alanine-b-lactone)s: Sequentially HTP and AROP

Efkan Çatıker; Ayçanur Hamzaçebi

Macromolecular Research, Vol.30, No.5, 305-313, May, 2022

DOI10.1007/s13233-022-0034-8 Export Citation

A Novel Strategy for Poly(β-alanine-b-lactone)s: Sequentially HTP and AROP

Efkan Çatıker^†, and Ayçanur Hamzaçebi

Department of Chemistry, Faculty of Art&Science, Ordu University, Ordu, 52200, Turkey

E-mail:

A series of poly(β-alanine-b-lactone)s were prepared by combination of hydrogen-transfer polymerization (HTP) of acrylamide and anionic ring-opening polymerization (AROP) of β-propiolactone, α-methyl propiolactone, β-butyrolactone, and δ-valerolactone. Poly-β-alanine (PBA) having a living anionic end-group for a further extension was obtained via HTP of acrylamide. Then, the anionic endgroup on PBA chains was used as initiation sites for AROP of the lactones. By varying acrylamide feeds, a series of copolymers was obtained with a hard segment (β-alanine) content between 6.86 and 36.82 mol%. Elemental analyses and spectral data (MALDI-MS, 1H-NMR, and FT-IR) for all new products were consistent with the proposed structures.

Keywords:AB-type block copolymers;poly(amide-ester);hydrogen transfer polymerization;ring-opening polymerization

[References]

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[2] Fitzpatrick SD, Fitzpatrick LE, Thakur A, Mazumder MAJ, Sheardown H, Expert Rev. Med. Devices, 9, 339 (2012)

[3] Ponjavic M, Nikolic MS, Nikodinovic-Runic J, Ilic-Tomic T, Djonlagic J, Int. J. Polym. Mater. Polym. Biomater., 68, 308 (2019)

[4] Galo GJ, Crepaldi EL, Grosso D, Sanchez C, Curr. Opin. Colloid Interface Sci., 8, 109 (2003)

[5] Li M, Ober CK, Mater. Today, 9, 30 (2006)

[6] Sandeau A, Mazières S, Destarac M, Polymer, 53, 5601 (2012)

[7] Myajtaszewski K, Spawnsick J, Mater. Today, 8, 26 (2005)

[8] Acar MH, Matyjaszewski K, Macromol. Chem. Phys., 200, 1094 (1999)

[9] Le D, Phan TNT, Autissier L, Charles L, Gigmes D, Polym. Chem., 7, 1659 (2016)

[10] Tinajero-Díaz E, Martínez-de Ilarduya A, Muñoz-Guerra S, de- Paz MV, Galbis E, Eur. Polym. J., 108, 380 (2018)

[11] Breslow DS, Hulse GE, Matlack AS, J. Am. Chem. Soc., 79, 3760 (1957)

[12] Rozenberg BA, Des. Monomers Polym., 7, 135 (2004)

[13] Rozenber BA, Macromol. Symp., 199, 443 (2003)

[14] Iwamura T, Tomita I, Suzuki M, Endo T, J. Polym. Sci. A: Polym. Chem., 37, 465 (1999)

[15] Gur’eva LL, Tkachuk AI, Dzhavadyan EA, Estrina GA, Surkov NF, Sulimenkov IV, Rozenberg BA, Polym. Sci. Ser. A, 49, 987 (2007)

[16] Trossarelli L, Guaita M, Camino G, J. Polym. Sci. C: Polym. Symp., 22, 721 (1969)

[17] Kumar K, Adhikary P, Tungala K, Azmeera V, Krishnamoorthi S, J. Appl. Polym. Sci., 132, 1 (2015)

[18] Roos K, Planes M, Bakkali-Hassani C, Mehats J, Vax A, Carlotti S, Macromolecules, 49, 2039 (2016)

[19] Masamoto J, Sasaguri K, Ohizumi C, Yamaguchi K, Kobayashi H, J. Appl. Polym. Sci., 14, 667 (1970)

[20] Lee MR, Stahl SS, Gellman SH, Masters KS, J. Am. Chem. Soc., 131, 16779 (2009)

[21] Dohm MT, Mowery BP, Czyzewski AM, Stahl SS, Gellman SH, Barron AE, J. Am. Chem. Soc., 132, 7957 (2010)

[22] Liu R, Vang KZ, Kreeger PK, Gellman SH, Masters KS, J. Biomed. Mater. Res. Part A, 100A, 2750 (2012)

[23] Chakraborty S, Liu R, Lemke JJ, Hayouka Z, Welch RA, Weisblum B, Masters KS, Gellman SH, ACS Macro Lett., 2, 753 (2013)

[24] Liu R, Masters KS, Gellman SH, Biomacromolecules, 13, 1100 (2012)

[25] Çatiker E, Konuk E, Gültan T, Gümüşderelioğlu M, Int. J. Polym. Mater. Polym. Biomater., 68, 338 (2019)

[26] Jedlinński Z, J. Heterocycl. Chem., 38, 1249 (2001)

[27] Albertsson AC, Varma IK, Biomacromolecules, 4, 1466 (2003)

[28] Mirmohammadi SA, Imani M, Uyama H, Atai M, Int. J. Polym. Mater. Polym. Biomater., 63, 624 (2014)

[29] Song Q, Pascouau C, Zhao J, Zhang G, Peruch F, Carlotti S, Prog. Polym. Sci, 110, 101309 (2020)

[30] Winnacker M, Rieger B, Polym. Chem., 7, 7039 (2016)

[31] Garg P, Keul H, Klee D, Möller M, Des. Monomers Polym., 12, 405 (2009)

[32] Fonseca AC, Gil MH, Simöes PN, Prog. Polym. Sci, 39, 1291 (2014)

[33] Karimi P, Rizkalla AS, Mequanint K, Materials, 3, 2346 (2010)

[34] Rodriguez-Galan A, Franco L, Puiggali J, Polymer, 3, 65 (2011)

[35] Lin S, Yu X, Tu Y, Xu H, Cheng SZD, Jia L, Chem. Commun., 46, 4273 (2010)

[36] Çatiker E, Meyvaci E, Atakay M, Salih B, Öztürk T, Polym. Bull., 76, 2113 (2019)

[37] Uzunlar A, Çatiker E, Hacettepe J. Biol. Chem., 3, 435 (2018)

[38] Penczek S, Duda A, Makromol. Chemie. Macromol. Symp., 67, 15 (1993)

[39] Penczek S, Cypryk M, Duda A, Kubisa P, Słomkowski S, Prog. Polym. Sci, 32, 247 (2007)

[40] Duda A, Kowalski A, in Handbook of Ring-Opening Polymerization, Dubois P, Coulembier O, Requez JM, Eds., WILEY-VCH Verlay GmbH & Co. KGaA, Weinheim, pp 1–51, 2009.

[41] Rodríguez-Galán A, Franco L, Puiggalí J, in Handbook of Biodegradable Polymers, Lendlein A, Sisson A, Eds., Wiley-VCH Verlag & Co. KGaA, Weinheim, Chap. 6, pp 133–154, 2011.

[42] Chae HG, Park SH, Kim BC, Kim DK, J. Polym. Sci. B: Polym. Phys., 42, 1759 (2004)

[43] Çatiker E, Öztürk T, Atakay M, Salih B, J. Macromol. Sci.-Pure Appl. Chem., 57, 600 (2020)

[44] Hong J, Cho D, Chang T, Shim WS, Lee DS, Macromol. Res., 11, 341 (2003)

[45] Girod M, Mazarin M, Phan TNT, Gigmes D, Charles L, J. Polym. Sci. A: Polym. Chem., 47, 3380 (2009)

[46] Chausson M, Fluchère AS, Landreau E, Aguni Y, Chevalier Y, Hamaide T, Abdul-Malak N, Bonnet I, Int. J. Pharm., 362, 153 (2008)

[47] Savaş B, Çatiker E, Öztürk T, Meyvaci E, J. Polym. Res., 28, 1 (2021)

[48] Pitsikalis M, Ionic Polymerization, in Reference Module in Chemistry, Molecular Sciences and Chemical Engineering, Elsevier, 2013.

[49] Hirao A, Goseki R, Ishizone T, Macromolecules, 47, 1883 (2014)

[50] Ishizone T, Goseki R, Eds. Kobayashi S, Müllen K, Berlin, Heidelberg, Springer Berlin Heidelberg, pp 1–18, 2021.