Syntheses And Characterizations Of Poly(ε-Caprolactone-b-Ethylene Glycol Methyl Ether) Block Copolymers Via Ring-Opening Polymerization And "Click" Chemistry

Year 2021, Volume: 11 Issue: 2, 1329 - 1340, 01.06.2021

Ergül Meyvacı , Temel Öztürk , Bedrettin Savaş

https://doi.org/10.21597/jist.836346

Cited By: 4

Abstract

Poly(ε-caprolactone-block-ethylene glycol methyl ether) [poly(RCL-b-mEG)] block copolymers were synthesized by "click" chemistry of polyethylene glycol methyl ether propargyl (mPEG-propargyl) and poly(ε-caprolactone) azido (RPCL-N3). Thus, mPEG-propargyl was acquired through the reaction of polyethylene glycol methyl ether with propargyl bromine. 2-[2-(2-Azidoethoxy)ethoxy]ethanol (N3ol) was synthesized by using 2-[2-(2-chloroethoxy)ethoxy]ethanol and sodium azide. Synthesis of RPCL-N3 was acquired using ROP of ε-caprolactone and N3ol. By using mPEG-propargyl and RPCL-N3, poly(RCL-b-mEG) block copolymers were obtained via "click" chemistry. The monofunctional homopolymers in the study were utilized for the syntheses of poly(RCL-b-mEG) block copolymers. The outputs were identified by scanning electron microscopy, 1H-nuclear magnetic resonance spectroscopy, differential scanning calorimetry, thermogravimetric analysis, Fourier-transform infrared spectroscopy, gel permeation chromatography, and dynamic light scattering instruments. The spectroscopic and thermal analysis of the block copolymers monitor that the copolymers were built through combination of ROP and "click" chemistry.

Keywords

Block copolymer, "click" chemistry, polyethylene glycol methyl ether propargyl, poly(ε-caprolactone) azido, ring-opening polymerization, 2-[2-(2-azidoethoxy)ethoxy]ethanol

Supporting Institution

Giresun üniversitesi

Project Number

FEN-BAP-C-281119-76

References

• Adams ML, Lavasanifar A, Kwon GS, 2003. Amphiphilic block copolymers for drug delivery. Journal of Pharmaceutical Sciences, 92 (7): 1343-1355.
• Altintas O, Tunca U, Barner-Kowollik C, 2011. Star and miktoarm star block (co)polymers via self-assembly of ATRP generated polymer segments featuring Hamilton wedge and cyanuric acid binding motifs. Polymer Chemistry, 2 (5): 1146-1155.
• Altıntas O, Tunca U, 2011. Synthesis of terpolymers by click reactions. Chemistry - An Asian Journal, 6 (10): 2584-2591.
• Bağlan M, Yıldıko Ü, Çakmak İ, Tekeş AT, 2018. Synthesis of PMMA-b-PEG-b-PMMA by controlled Polymerization Using Macro-RAFT Agents. Journal of the Institute of Science and Technology, 8 (3): 243-254
• Baker YR, Galloway WRJD, Hodgkinson JT, Spring DR, 2013. Design and synthesis of a biotinylated chemical probe for detecting the molecular targets of an inhibitor of the production of the pseudomonas aeruginosa virulence factor pyocyanin. Molecules, 18 (10): 11783-11796.
• Barner-Kowollik C, Du Prez FE, Espeel P, Hawker CJ, Junkers T, Schlaad H, Camp WV, 2011. "Clicking" polymers or just efficient linking: what is the difference? Angewandte Chemie International Edition, 50 (1): 60-62.
• Binder WH, Sachsenhofer, R, 2007. "Click" chemistry in polymer and materials science. Macromolecular Rapid Communications, 28 (1): 15-54.
• Bolton J, Rzayev J, 2012. Tandem RAFT-ATRP synthesis of polystyrene-poly(methyl methacrylate) bottlebrush block copolymers and their self-assembly into cylindrical nanostructures. ACS Macro Letters, 1 (1): 15-18.
• Çatıker E, Öztürk T, Atakay M, Salih B, 2020. Synthesis and characterization of the ABA-type poly(ester-ether-ester) block copolymers. Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, 57 (8): 600-609.
• Çatıker E, Öztürk T, Atakay M, Salih B, 2019. Synthesis and characterization of novel ABA type poly(ester-ether) triblock copolymers. Journal of Polymer Research, 26 (5): 123.
• Çatıker E, Meyvacı E, Atakay M, Salih B, Öztürk, T, 2019. Synthesis and characterization of amphiphilic triblock copolymers including β-alanine/α-methyl-β-alanine and ethylene glycol by "click" chemistry. Polymer Bulletin, 76 (4): 2113-2128.
• Coulembier O, Degee P, Hedrick JL, Dubois P, 2006. From controlled ring-opening polymerization to biodegradable aliphatic polyester: especially poly(beta-malic acid) derivatives. Progress in Polymer Science, 31 (8): 723-747.
• Erciyes AT, Erim M, Hazer B, Yağcı Y, 1992. Synthesis of polyacrylamide flocculants with poly(ethylene glycol) segments by redox polymerization. Die Angewandte Makromolekulare Chemie, 200 (1): 163-171.
• Gacal B, Durmaz H, Tasdelen MA, Hizal G, Tunca U, Yagci Y, Demirel AL, 2006. Anthracene-maleimide-based Diels-Alder "click chemistry" as a novel route to graft copolymers. Macromolecules, 39 (16): 5330–5336.
• Göktaş M, Öztürk T, Atalar MN, Tekeş AT, Hazer B, 2014. One-step synthesis of triblock copolymers via simultaneous reversible-addition fragmentation chain transfer (RAFT) and ring-opening polymerization using a novel difunctional macro-RAFT agent based on polyethylene glycol. Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, 51 (11): 854-863.
• Hizal G, Sakar D, Tunca U, 2005. Synthesis of tri-arm star di-block co-polymer containing poly(tetrahydrofuran-b-methyl methacrylate) arms via combination of cationic ring-opening polymerization and photosensitized free radical polymerization routes. Designed Monomers and Polymers, 8 (6): 609-617.
• Jamshid MR, 2008. Synthesis and thermal properties of novel multiblock biodegradable copolymers derived from polyethylene glycol, ε-caprolactone and p-dioxanone. ScienceAsia, 34 (2): 207-213.
• Kolb HC, Finn MG, Sharpless KB, 2001. Click chemistry: diverse chemical function from a few good reactions. Angewandte Chemie International Edition, 40 (11): 2004-2021.
• Lakouraj MM, Hasantabar V, Bagheri N, 2013. Synthesis of polyethers containing triazole units in the backbone by click chemistry in a tricomponent reaction. Journal of Polymers, 2013, 167106.
• Öztürk T, Hazer B, 2010. Synthesis and characterization of a novel macromonomer initiator for reversible addition fragmentation chain transfer (RAFT). Evaluation of the polymerization kinetics and gelation behaviors. Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, 47 (3): 265-272.
• Öztürk T, Savaş B, Meyvacı E, Kılıçlıoğlu A, Hazer B, 2020. Synthesis and characterization of the block copolymers using the novel bifunctional initiator by RAFT and FRP technics: evaluation of the primary polymerization parameters. Journal of Polymer Research, 27 (3): 76.
• Öztürk T, Kayğın O, Göktaş M, Hazer B, 2016. Synthesis and characterization of graft copolymers based on polyepichlorohydrin via reversible addition-fragmentation chain transfer polymerization. Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, 53 (6): 362-367.
• Öztürk T, Göktaş M, Hazer B, 2011. Synthesis and characterization of poly(methyl methacrylate-block-ethylene glycol-block-methyl methacrylate) block copolymers by reversible addition-fragmentation chain transfer polymerization. Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, 48 (1): 65-70.
• Öztürk S, Cakmak İ, Tekeş AT, Yıldıko Ü, 2019. Synthesis and Characterization of Poly (lactic acid-b-ε-caprolactone) Block Copolymers. Journal of the Institute of Science and Technology, 9 (2): 1035-1045.
• Öztürk T, Kılıçlıoğlu A, Savaş B, Hazer B, 2018. Synthesis and characterization poly(ɛ-caprolactone-co-ethylene glycol) heteroarm star-type amphiphilic copolymers by "click" chemistry and ring-opening polymerization. Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, 55 (8): 588-594.
• Öztürk T, Yavuz M, Göktaş M, Hazer B, 2016. One-step synthesis of triarm block copolymers by simultaneous atom transfer radical and ring-opening polymerization. Polymer Bulletin, 73 (6): 1497-1513.
• Öztürk T, Meyvacı E, 2017. Synthesis and characterization poly(ɛ-caprolactone-b-ethylene glycol-b-ɛ-caprolactone) block copolymers via "click" chemistry and ring-opening polymerization. Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, 54 (9): 575-581.
• Öztürk T, Meyvacı E, Bektaş H, Menteşe E, 2019. Synthesis and characterization of ring type and branched polymers including polyethylene glycols by "click" chemistry, SN Applied Sciences, 1 (4): 343.
• Öztürk T, Meyvacı E, Arslan T, 2020. Synthesis and characterization of poly(vinyl chloride-g-ε-caprolactone) brush type graft copolymers by ring opening polymerization and "click" chemistry. J Macromol Sci Part A, 57 (3): 171-180.
• Öztürk T, Yörümez C, 2020. Synthesis of block copolymer including polyepichlorohydrin and polyethylene glycol by "click" chemistry: evaluation of primary parameters of copolymerization. Polymer Bulletin, 77, 4773-4788.
• Öztürk T, Cavicchi, CA, 2018. Synthesis and characterization of poly(epichlorohydrin-g-ε-caprolactone) graft copolymers by "click" chemistry. Journal of Polymer Materials, 35 (2): 209-220.
• Moses JE, Moorhouse AD, 2007. The growing applications of click chemistry. Chemical Society Reviews, 36 (8): 1249-1262.
• Riess G, 2003. Micellization of block copolymers. Progress in Polymer Science, 28 (7):1107-1170.
• Rukmanikrishnan B, Muthusamy S, 2018. Preparation and properties of polyimides containing 1,2,3-triazole moieties. Advances in Polymer Technology, 37 (1): 21641.
• Ruzette AV, Leibler L, 2005. Block copolymers in tomorrow's plastics. Nature Materials, 4 (1): 19-31.
• Şanal T, Koçak İ, Hazer B, 2017. Synthesis of comb-type amphiphilic graft copolymers derived from chlorinated poly(ε-caprolactone) via click reaction. Polymer Bulletin, 74 (4): 977-995.
• Savaş B, Öztürk T, Meyvacı E, Hazer B, 2020. Synthesis and characterization of comb-type graft copolymers by redox polymerization and "click" chemistry method. SN Applied Sciences, 2 (2): 181.
• Thanomsilp C, Phetthianchai U, 2012. Synthesis and characterization of PLA-co-PEG copolymers. Advanced Materials Research, 506, 178-181.
• Tunca U, 2018. Click and multicomponent reactions work together for polymer chemistry. Macromolecular Chemistry and Physics, 219 (16): 1800163.
• Tunca, U, 2013. Triple click reaction strategy for macromolecular diversity. Macromolecular Rapid Communications, 34 (1): 38-46.
• Zhu DY, Cao GS, Qiu WL, Rong MZ, Zhang MQ, 2015. Self-healing polyvinyl chloride (PVC) based on microencapsulated nucleophilic thiol-click chemistry. Polymer, 69, 1-9.
• Xu J, Ye J, Liu SY, 2007. Synthesis of well-defined cyclic poly(N-isopropylacrylamide) via click chemistry and its unique thermal phase transition behavior. Macromolecules, 40 (25): 9103-9110.
• Xi W, Scott TF, Kloxin CJ, Bowman CN, 2014. Click chemistry in materials science. Advanced Functional Materials, 24 (18): 2572-2590.