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Polymer Bulletin

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01.07.2013 | Original Paper

Synthesis of polysulfone-b-polystyrene block copolymers by mechanistic transformation from condensation polymerization to free radical polymerization

verfasst von: Cemil Dizman, Muhammet U. Kahveci, Yusuf Yagci

Erschienen in: Polymer Bulletin | Ausgabe 7/2013

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Abstract

Synthesis of polysulfone-b-polystyrene (PSU-b-PS) block copolymers by a combination of condensation polymerization and free radical polymerization processes are described. First, a new macroazoinitiator (MAI) containing polysulfone (PSU) units was prepared by direct esterification of 4,4-azobis(4-cyanopentanoic acid) with α,ω-hydroxyl PSU telechelics at ambient conditions. The macroinitiator was then used in conventional free radical polymerization of styrene leading to the formation of desired block copolymers. In this process, initiating macroradicals were generated by thermal cleavage of the azo group present in the macroazoinitiator structure. The precursor polysulfone macroazoinitiator (PSU-MAI) and resulting block copolymers were characterized by spectral analysis using FT-IR, ¹H-NMR, GPC, TGA, and DSC.

Vorheriger Artikel Control over crystalline form in polypropylene pipe via mandrel rotation extrusion

Nächster Artikel Styrene copolymerization using a metallocene-MAO initiator system. Homo- and copolymerization of styrene with some cycloalkenes

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Mishra MK, Yagci Y (2009) Handbook of vinyl polymers: radical polymerization, process, and technology. CRC Press, Boca Raton

Nalwa HS (2001) Advanced functional molecules and polymers. Gordon & Breach, Australia

Zhao DY, Huo QS, Feng JL, Chmelka BF, Stucky GD (1998) Nonionic triblock and star diblock copolymer and oligomeric surfactant syntheses of highly ordered, hydrothermally stable, mesoporous silica structures. J Am Chem Soc 120(24):6024–6036. doi:10.1021/ja974025i CrossRef

Bates FS, Fredrickson GH (1999) Block copolymers—designer soft materials. Phys Today 52(2):32–38. doi:10.1063/1.882522 CrossRef

Kataoka K, Harada A, Nagasaki Y (2001) Block copolymer micelles for drug delivery: design, characterization and biological significance. Adv Drug Deliv Rev 47(1):113–131. doi:10.1016/s0169-409x(00)00124-1 CrossRef

Discher DE, Eisenberg A (2002) Polymer vesicles. Science 297(5583):967–973. doi:10.1126/science.1074972 CrossRef

Jeong B, Bae YH, Lee DS, Kim SW (1997) Biodegradable block copolymers as injectable drug-delivery systems. Nature 388(6645):860–862CrossRef

Liu JQ, Zhang Q, Remsen EE, Wooley KL (2001) Nanostructured materials designed for cell binding and transduction. Biomacromolecules 2(2):362–368. doi:10.1021/bm015515c CrossRef

Rzaev ZMO, Dincer S, Piskin E (2007) Functional copolymers of n-isopropylacrylamide for bioengineering applications. Prog Polym Sci 32(5):534–595. doi:10.1016/j.progpolymsci.2007.01.006 CrossRef

10.

Chiefari J, Chong YK, Ercole F, Krstina J, Jeffery J, Le TPT, Mayadunne RTA, Meijs GF, Moad CL, Moad G, Rizzardo E, Thang SH (1998) Living free-radical polymerization by reversible addition-fragmentation chain transfer: the raft process. Macromolecules 31(16):5559–5562. doi:10.1021/ma9804951 CrossRef

11.

Hawker CJ, Bosman AW, Harth E (2001) New polymer synthesis by nitroxide mediated living radical polymerizations. Chem Rev 101(12):3661–3688. doi:10.1021/cr990119u CrossRef

12.

Matyjaszewski K, Xia JH (2001) Atom transfer radical polymerization. Chem Rev 101(9):2921–2990. doi:10.1021/cr940534g CrossRef

13.

Guo YM, Pan CY, Wang J (2001) Block and star block copolymers by mechanism transformation. Vi. Synthesis and characterization of a(4)b(4) miktoarm star copolymers consisting of polystyrene and polytetrahydrofuran prepared by cationic ring-opening polymerization and atom transfer radical polymerization. J Polym Sci 39(13):2134–2142

14.

Xu YJ, Pan CY (2000) Block and star-block copolymers by mechanism transformation. 3. S-(PTHF-PSt)(4) and S-(PTHF-PSt-PMMA)(4) from living crop to ATRP. Macromolecules 33(13):4750–4756CrossRef

15.

Xu YJ, Pan CY (2000) Block and star block copolymers by mechanism transformation. I. Synthesis of PTHF-PST-PTHF by the transformation of ATRP into crop. J Polym Sci A 38(2):337–344CrossRef

16.

Guo YM, Pan CY (2001) Block and star block copolymers by mechanism transformation. Part V. Syntheses of polystyrene/polytetrahydrofuran A2B2 miktoarm star copolymers by transformation of crop into ATRP. Polymer 42(7):2863–2869CrossRef

17.

Yagci Y, Serhatli IE, Kubisa P, Biedron T (1993) Synthesis of block copolymers by combination of an activated monomer and free-radical polymerization mechanism. Macromolecules 26(10):2397–2399CrossRef

18.

Yagci Y, Tasdelen MA (2006) Mechanistic transformations involving living and controlled/living polymerization methods. Prog Polym Sci 31(12):1133–1170. doi:10.1016/j.progpolymsci.2006.07.003 CrossRef

19.

Cianga I, Senyo T, Ito K, Yagci Y (2004) Electron transfer reactions of radical anions with tempo: a versatile route for transformation of living anionic polymerization into stable radical-mediated polymerization. Macromol Rapid Comm 25(19):1697–1702CrossRef

20.

Tasdelen MA, Yagci Y, Demirel AL, Biedron T, Kubisa P (2007) Synthesis and characterization of block-graft copolymers poly(epichlorohydrin-b-styrene)-g-poly(methyl methacrylate) by combination of activated monomer polymerization, nmp and atrp. Polym Bull 58(4):653–663. doi:10.1007/s00289-006-0708-y CrossRef

21.

Yagci Y, Duz AB, Onen A (1997) Controlled radical polymerization initiated by stable radical terminated polytetrahydrofuran. Polymer 38(11):2861–2863CrossRef

22.

Yagci Y (1985) Block copolymers by combinations of cationic and radical routes.1. A new difunctional azo-oxocarbenium initiator for cationic polymerization. Polymer. Communications 26(1):7–8

23.

Hizal G, Yagci Y, Schnabel W (1994) N-alkoxy pyridinium ion terminated polytetrahydrofurans—synthesis and their use in photoinitiated block copolymerization. Polymer 35(20):4443–4448CrossRef

24.

Galli G, Chiellini E, Yagci Y, Serhatli EI, Laus M, Bignozzi MC, Angeloni AS (1993) Block copolymers with crystalline and side-chain liquid-crystalline blocks. Makromol Chem, Rapid Commun 14(3):185–193CrossRef

25.

Yagci Y, Onen A, Schnabel W (1991) Block copolymers by combination of radical and promoted cationic polymerization routes. Macromolecules 24(16):4620–4623CrossRef

26.

Duz AB, Yagci Y (1999) Synthesis of block copolymers by combination of atom transfer radical and promoted cationic polymerization mechanisms. Eur Polym J 35(11):2031–2038CrossRef

27.

Durmaz YY, Kukut M, Moszner N, Yagci Y (2009) Sequential photodecomposition of bisacylgermane type photoinitiator: synthesis of block copolymers by combination of free radical promoted cationic and free radical polymerization mechanisms. J Polym Sci A 47(18):4793–4799. doi:10.1002/pola.23533 CrossRef

28.

Serhatli IE, Galli G, Yagci Y, Chiellini E (1995) Synthesis of hybrid liquid-crystalline block-copolymers by combination of cationic or promoted cationic and free-radical polymerizations. Polym Bull 34(5–6):539–546. doi:10.1007/bf00423349 CrossRef

29.

Hizal G, Sarman A, Yagci Y (1995) Synthesis of hydroxy-terminated polytetrahydrofuran by photoinduced process. Polym Bull 35(5):567–573CrossRef

30.

Durmaz YY, Yilmaz G, Yagci Y (2007) N-alkoxy pyridinium ion terminated polystyrenes: a facile route to photoinduced block copolymerization. J Polym Sci A 45(3):423–428CrossRef

31.

Acik G, Kahveci MU, Yagci Y (2010) Synthesis of block copolymers by combination of atom transfer radical polymerization and visible light radical photopolymerization methods. Macromolecules 43(21):9198–9201. doi:10.1021/ma101967w CrossRef

32.

Yagci Y (1986) Block copolymers by combinations of cationic and radical routes. 2. Use of polymers with acyl chloride terminal groups in oxocarbenium polymerization. Polymer. Communications 27(1):21–22

33.

Denizligil S, Baskan A, Yagci Y (1995) Bifunctional polytetrahydrofuran initiator for sequential photochemical and thermal initiation. Macromol Rapid Comm 16(5):387–391CrossRef

34.

Ren Q, Zhang HJ, Zhang XK, Huang BT (1993) Hydrogenated polybutadiene polymethyl methacrylate (HPB PMMA) block copolymer .1. Synthesis of polybutadiene polymethyl methacrylate (PB PMMA) block copolymer. J Polym Sci A 31(4):847–851. doi:10.1002/pola.1993.080310401

35.

Tunca U, Serhatli IE, Yagci Y (1989) Polymerization of acrylamide initiated by the redox system Ce(IV)-4,4′-azobis (4-cyano pentanol). Polym Bull 22(5–6):483–488CrossRef

36.

Hizal G, Yagci Y (1989) Block copolymers by combination of cationic and radical routes.4. Cationic polymerization of tetrahydrofuran initiated by difunctional azo-oxocarbenium initiator. Polymer 30(4):722–725. doi:10.1016/0032-3861(89)90162-6 CrossRef

37.

Hazer B, Erdem B, Lenz RW (1994) Styrene polymerization with some new macro or macromonomeric azoinitiators having peg units. J Polym Sci A 32(9):1739–1746. doi:10.1002/pola.1994.080320916 CrossRef

38.

Haneda Y, Terada H, Yoshida M, Ueda A, Nagai S (1994) Macro-azo-initiators composed of various polyesters—their syntheses, thermal-properties, and application to block copolymerization. J Polym Sci A 32(14):2641–2652. doi:10.1002/pola.1994.080321405 CrossRef

39.

Simionescu CI, David G, Ioanid A, Paraschiv V, Riess G, Simionescu BC (1994) Solution polymerization of vinyl monomers in the presence of poly(n-acetyliminoethylene) macroazoinitiators. J Polym Sci A 32(16):3123–3132. doi:10.1002/pola.1994.080321612 CrossRef

40.

Tunca U, Yagci Y (1990) Synthesis, decomposition, and initiator properties of macroazonitriles for the preparation of polymers with crown ether units. J Polym Sci A 28(7):1721–1733. doi:10.1002/pola.1990.080280705 CrossRef

41.

Nuyken O, Weidner R (1986) Graft and block copolymers via polymeric azo initiators. Adv Polym Sci 73–74:145–199CrossRef

42.

Kim DK, Lee SB, Doh KS, Nam YW (1999) Synthesis of block copolymers having perfluoroalkyl and silicone-containing side chains using diazo macroinitiator and their surface properties. J Appl Polym Sci 74(8):1917–1926. doi:10.1002/(SICI)1097-4628(19991121)74:8<1917:AID-APP5>3.0.CO;2-G CrossRef

43.

Cheikhalard T, Tighzert L, Pascault JP (1996) Polyurethane macroazoinitiators based on 2,2′-azobis(2-cyanopropanol) kinetic studies. J Appl Polym Sci 62(13):2365–2375. doi:10.1002/(SICI)1097-4628(19961226)62:13<2365:AID-APP22>3.0.CO;2-0 CrossRef

44.

Uyanik N, Baysal BM (1990) Preparation of polystyrene-block-(ethylene oxide)s and characterization of the products. J Appl Polym Sci 41(9–10):1981–1993. doi:10.1002/app.1990.070410905 CrossRef

45.

Chang TC, Chen HB, Chen YC, Ho SY (1996) Characterization of azo-containing polydimethylsiloxanes and their copolymers with methyl methacrylate. J Polym Sci A 34(13):2613–2620. doi:10.1002/(SICI)1099-0518(19960930)34:13<2613:AID-POLA7>3.0.CO;2-S CrossRef

46.

Shimura Y, Chen DJ (1993) Thermodegradable polyurethanes having azo groups in the main chains. 1. Synthesis and thermal properties. Macromolecules 26(19):5004–5008. doi:10.1021/ma00071a003 CrossRef

47.

Olabisi O (1997) Handbook of thermoplastics. Marcel Dekker, New York. http://worldcat.org; http://search.ebscohost.com/login.aspx?direct=true&scope=site&db=nlebk&db=nlabk&AN=12621

48.

Wang F, Hickner M, Kim YS, Zawodzinski TA, McGrath JE (2002) Direct polymerization of sulfonated poly(arylene ether sulfone) random (statistical) copolymers: candidates for new proton exchange membranes. J Membr Sci 197(1–2):231–242. doi:10.1016/s0376-7388(01)00620-2 CrossRef

49.

Hickner MA, Ghassemi H, Kim YS, Einsla BR, McGrath JE (2004) Alternative polymer systems for proton exchange membranes (PEMs). Chem Rev 104(10):4587–4611. doi:10.1021/cr020711a CrossRef

50.

Guiver MD, Robertson GP, Yoshikawa M, Tam CM (2000) Functionalized polysulfones: Methods for chemical modification and membrane applications. In: Pinnau I, Freeman BD (eds) Membrane formation and modification, vol 744, ACS symposium series, pp 137–161

51.

Paul M, Park HB, Freeman BD, Roy A, McGrath JE, Riffle JS (2008) Synthesis and crosslinking of partially disulfonated poly(arylene ether sulfone) random copolymers as candidates for chlorine resistant reverse osmosis membranes. Polymer 49(9):2243–2252. doi:10.1016/j.polymer.2008.02.039 CrossRef

52.

Higuchi A, Sugiyama K, Yoon BO, Sakurai M, Hara M, Sumita M, Sugawara S, Shirai T (2003) Serum protein adsorption and platelet adhesion on pluronic (TM)-adsorbed polysulfone membranes. Biomaterials 24(19):3235–3245. doi:10.1016/s0142-9612(03)00186-8 CrossRef

53.

Zhao CS, Liu XD, Nomizu M, Nishi N (2003) Blood compatible aspects of DNA-modified polysulfone membrane-protein adsorption and platelet adhesion. Biomaterials 24(21):3747–3755. doi:10.1016/s0142-9612(03)00250-3 CrossRef

54.

Cureton LT, Beyer FL, Turner SR (2010) Synthesis and characterization of hexafluoroisopropylidene bisphenol poly(arylene ether sulfone) and polydimethylsiloxane segmented block copolymers. Polymer 51(8):1679–1686. doi:10.1016/j.polymer.2010.02.010 CrossRef

55.

Bai Z, Houtz MD, Mirau PA, Dang TD (2007) Structures and properties of highly sulfonated poly(arylenethioethersulfone)s as proton exchange membranes. Polymer 48(22):6598–6604. doi:10.1016/j.polymer.2007.08.052 CrossRef

56.

Chen Y, Guo R, Lee CH, Lee M, McGrath JE (2012) Partly fluorinated poly(arylene ether ketone sulfone) hydrophilic-hydrophobic multiblock copolymers for fuel cell membranes. Int J Hydrogen Energy 37(7):6132–6139. doi:10.1016/j.ijhyene.2011.06.139 CrossRef

57.

Lee CH, Xie W, VanHouten D, McGrath JE, Freeman BD, Spano J, Wi S, Park CH, Lee YM (2012) Hydrophilic silica additives for disulfonated poly(arylene ether sulfone) random copolymer membranes. J Membrane Sci 392:157–166. doi:10.1016/j.memsci.2011.12.015 CrossRef

58.

Dizman C, Ates S, Torun L, Yagci Y (2010) Synthesis, characterization and photoinduced curing of polysulfones with (meth)acrylate functionalities. Beilstein J Org Chem 6:56. doi:10.3762/bjoc.6.56

59.

Ates S, Dizman C, Aydogan B, Kiskan B, Torun L, Yagci Y (2011) Synthesis, characterization and thermally activated curing of polysulfones with benzoxazine end groups. Polymer 52(7):1504–1509. doi:10.1016/j.polymer.2011.01.051 CrossRef

60.

Dizman C, Ates S, Uyar T, Tasdelen MA, Torun L, Yagci Y (2011) Polysulfone/clay nanocomposites by in situ photoinduced crosslinking polymerization. Macromol Mater Eng 296(12):1101–1106. doi:10.1002/mame.201100114 CrossRef

61.

Dizman C, Demirkol DO, Ates S, Torun L, Sakarya S, Timur S, Yagci Y (2011) Photochemically prepared polysulfone/poly(ethylene glycol) amphiphilic networks and their biomolecule adsorption properties. Colloids Surf B 88(1):265–270. doi:10.1016/j.colsurfb.2011.06.042 CrossRef

62.

Toiserkani H, Yilmaz G, Yagci Y, Torun L (2010) Functionalization of polysulfones by click chemistry. Macromol Chem Physic 211(22):2389–2395. doi:10.1002/macp.201000245 CrossRef

63.

Karadag M, Yilmaz G, Toiserkani H, Demirkol DO, Sakarya S, Torun L, Timur S, Yagci Y (2011) Polysulfone/pyrene membranes: a new microwell assay platform for bioapplications. Macromol Biosci 11(9):1235–1243. doi:10.1002/mabi.201100024 CrossRef

64.

Yilmaz G, Toiserkani H, Demirkol DO, Sakarya S, Timur S, Torun L, Yagci Y (2011) Polysulfone based amphiphilic graft copolymers by click chemistry as bioinert membranes. Mater Sci Eng C 31(5):1091–1097. doi:10.1016/j.msec.2011.03.010 CrossRef

65.

Yilmaz G, Toiserkani H, Demirkol DO, Sakarya S, Timur S, Yagci Y, Torun L (2011) Modification of polysulfones by click chemistry: amphiphilic graft copolymers and their protein adsorption and cell adhesion properties. J Polym Sci A 49(1):110–117. doi:10.1002/pola.24424 CrossRef

66.

Hazer B, Ayas A, Besirli N, Saltek N, Baysal BM (1989) Preparation of ABCBA-type block copolymers by use of macro-initiators containing peroxy and azo groups. Makromol Chem 190(8):1987–1996CrossRef

67.

Tasdelen MA, Kahveci MU, Yagci Y (2011) Telechelic polymers by living and controlled/living polymerization methods. Prog Polym Sci 36(4):455–567. doi:10.1016/j.progpolymsci.2010.10.002 CrossRef

68.

Yagci Y, Mishra MK (1994) Macroinitiators in multi-mode polymerization. In: Mishra MK (ed) Macromolecular design: concept and practice (macromonomers, macroinitiators, macroiniferters, macroinimers, macroinifers, macroiniters). Polymer Frontiers International, Hopewell Jct, New York

69.

Simon J, Bajpai A (2001) Synthesis of macroazoinitiator by direct polycondensation for block copolymerization of styrene and butadiene. J Appl Polym Sci 82(12):2922–2933. doi:10.1002/app.2148 CrossRef

70.

Markova D, Kumar A, Klapper M, Muellen K (2009) Phosphonic acid-containing homo-, AB and BAB block copolymers via ATRP designed for fuel cell applications. Polymer 50(15):3411–3421. doi:10.1016/j.polymer.2009.06.011 CrossRef

71.

Kumar A, Pisula W, Markova D, Klapper M, Muellen K (2012) Proton-conducting poly(phenylene oxide)–poly(vinyl benzyl phosphonic acid) block copolymers via atom transfer radical polymerization. Macromol Chem Phys 213(5):489–499. doi:10.1002/macp.201100429 CrossRef

Titel: Synthesis of polysulfone-b-polystyrene block copolymers by mechanistic transformation from condensation polymerization to free radical polymerization
verfasst von: Cemil Dizman
Muhammet U. Kahveci
Yusuf Yagci
Publikationsdatum: 01.07.2013
Verlag: Springer-Verlag
Erschienen in: Polymer Bulletin / Ausgabe 7/2013
Print ISSN: 0170-0839
Elektronische ISSN: 1436-2449
DOI: https://doi.org/10.1007/s00289-013-0931-2

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