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Synthesis and Characterization of Poly(linoleic acid)-g-poly(Nisopropylacrylamide)-g-poly (D, L-lactide) Graft Copolymers by Onepot Polymerization Method

Year 2018, Volume: 6 Issue: 4, 1321 - 1334, 01.08.2018
https://doi.org/10.29130/dubited.434025

Abstract

In this study, one-pot three-block graft copolymers were synthesized using a combination of ring opening polymerization and free radical polymerization of Auto-oxidized polymeric linoleic acid peroxide (PLina). Graft copolymers with poly(linoleic acid)-g-poly(N-isopropylacrylamide)-g-poly(D,L-lactide) structure were synthesized the free radical polymerization with N-isopropylacrylamide (NIPAM) in monomer the main chain of PLina and the ring opening polymerization of the D, L-lactide (LA) monomer with carboxylic acid groups of PLina with together. The basic parameters such as polymerization time, initiator concentration and monomer concentration affecting the one-pot polymerization reaction were investigated. Characterization of the obtained graft copolymers were carried out using 1H NMR and GPC techniques.

References

  • M. M. Reddy, S. Vivekannandhan, M. Misra, K. S. Bhatia and K. A. Mohanty Biobased, “plastics and bionanocomposites: Current statuse and future opportunities”, Progress in Polymer Science, 38, 1653-1689, 2013.
  • G. Lligadas, J. C. Ronda, M. Galia and V. Cadiz, “Renewable polymeric materials from vegetable oils: a perspective” Materials Today, 9, 2013.
  • W. B. Chieng, N. A. İbrahim, Y. Y. Then and Y. Y. Loo, “Epoxidized Vegetable Oils Plasticized Poly(lactic acid) Biocomposites: Mechanical, Thermal and Morphology Properties”, Molecules, 19, 16024-10638, 2014.
  • M. W. Gramlich, M. L. Robertson, and M. A. Hillmyer, “Reactive Compatibilization of Poly( L-lactid) and Conjugated Soybean Oil”, Macromolecules, 43, 2313-2321, 2010.
  • E. Kılıçay, B. Çakmaklı, B. Hazer, B. E. Denkbaş and B. Açıkgöz, “Acetylsalicylic(Acid Loading and Release Studies of the PMMA-g-Polymeric Oils/Oily Acids Micro and Nanospheres”, Journal of Applied Polymer Science, 3, 1610-1618, 2010.
  • B. Çakmaklı, B. Hazer, I. O. Tekin, S. Kızgut, M. Köksal, and Y. Menceloğlu, “Synthesis and characterization of polymeric linseed oil grafted methyl methacrylate or styrene”, Macromol. Biosci., 4, 649-655, 2004.
  • B. Çakmaklı, B. Hazer, . O. Tekin and F. B. Cömert, “Synthesis and characterization of polymeric soybean oil-g-methyl methacrylate (and n-butyl methacrylate) grafted copolymers: Biocompatibility and bacterial adhesion”, Biomacromolecules, 6, 1750-1758, 2005.
  • E. Keleş and B. Hazer, “Autooxidized Polyunsaturated Oil/Oily Acids: Post-it Application and Reaction with Fe(III) and Adhesion Properties” Macromolecular Symposia, 269,154-160, 2008.
  • A. Allı, and B Hazer, “Poly(N-isopropylacrylamide) thermoresponsive cross-linked conjugates containing polymeric soybean oil and/or polypropylene glycol”, Eur. Polym. Jour., 44, 1701-1713, 2008.
  • A. Allı, T. Şanal, B. Hazer, “Redox polymerization of N-isopropylacrylamide by using hydroxylated soya oil polymer”, Tur. Jour. Chem., 39, 382-394, 2015.
  • E. Kılıçay, B. Çakmaklı, B. Hazer, E. B. Denkbas, and B. Açıkgöz, “Acetylsalicylic acid loading and release studies of the PMMA-g-Poymeric oils/oily acids micro and nanospheres”, Journal of Applied Polymer Science, 119(3), 1610-1618, 2011.
  • A. Allı, S. Allı, C. R. Becer and B. Hazer, “One-pot synthesis of poly(linoleic acid)-g-poly (styrene)-g-poly(ε-caprolactone) graft copolymers”, J. Amer. Oil Chem. Soc. (JAOCS), 91, 849–858, 2014.
  • S. Allı, R. S. Aydın Tığlı,, A. Allı and B. Hazer, “Biodegradable Poly(ε-Caprolactone)- Based Graft Copolymers:Via Poly(Linoleic Acid): In Vitro Enzymatic Evaluation”, J. Amer. Oil. Chem. Soc., 92, 449-458, 2015.
  • A. Allı, S. Allı, C. R. Becer and B. Hazer, “Nitroxide mediated copolymerization of styrene and pentafluorostyrene initiated by polymeric linoleic acid”, European Journal of Lipid Science and Technology, 118 (2), 279-287, 2016.
  • A. Allı, Y. Arı and M. Gökçen, “Novel Poly(linolenic acid) Graft Copolymers: Synthesis, Characterization and Electrical Properties”, J. Am. Oil Chem. Soc., 93, 895–904, 2016.
  • T. Öztürk, M. Göktaş and B. Hazer, “One-Step Synthesis of Triarm Block Copolymers via Simultaneous Reversible-Addition Fragmentation Chain Transfer and Ring- Opening Polymerization”, J. Appl. Polym. Sci., 117, 1638–1645, 2010.
  • T. Öztürk, and İ. Cakmak ,“One-step synthesis of multiphase block copolymers via simultaneus free radical and ring opening polymerization using poly(ethylene oxide) possessing azo group”, J Macromol. Sci. Part A Pure and Appl. Chem., 45, 572–577. 2008.
  • M. Le Hellaye, C. Lefay, T.P. Davis, M. H. Stenzel and C. J. Barner-Kowollik. “Simultaneous reversible addition fragmentation chain transfer and ring-opening polymerization”,. J. Polym. Sci. Part A. Polym. Chem., 46: 3058-3067, 2008.
  • Y. C. Yu, G. Li, H. U. Kang and J. U. Youk , “One-step synthesis of poly(alkyl methacrylate)-b-polyester block copolymers via a dual initiator route combining RAFT polymerization and ROP”, Coll. Polym. Sci., 290: 1707-1712, 2012.
  • M. K. Mahanthappa, F. S. Bates and M. A. Hillmyer, “ Synthesis of ABA triblock copolymers by a tandem ROMP-RAFT strategy”, Macromolecules, 38:7890-7894, 2005.
  • H. Mori, S. Masuda and T. Endo, “Ring-opening copolymerization of 10-methylene-9,10 dihydroanthryl-9-spirophenylcyclopropane via free radical and RAFT processes”, Macromolecules, 41: 632–639, 2008.
  • D. H Han and C. Y. Pan, , “ Preparation and characterization of heteroarm H-shaped Terpolymers by combination of reversible addition-fragmentation transfer polymerization and ring-opening polymerization”, J. Polym. Sci. Part A Polym. Chem., 45, 789-799, 2007.
  • X. W. Xu and J. L. Huang, “Synthesis and characterization of amphiphilic copolymer of linear poly(ethylene oxide) linked with [poly(styrene-co-2-hydroxyethyl methacrylate)-graft-poly(epsilon-caprolactone)] using sequential controlled polymerization”, J. Polym. Sci. Part A. Polym. Chem., 44: 467-476, 2006.
  • J. Liu and C. Y. Pan, Synthesis and characterization of H-shaped copolymers by combination of RAFT polymerization and CROP”, Polymer, 46, 11133-11141, 2005.
  • J. Hong, Q. Wang, and Z. Fan, “Synthesis of multiblock polymer containing narrow polydispersity blocks”, Macromol. Rapid Commun., 27, 57-62, 2006.
  • C. Cheng, E. Khoshdel and K. L Wooley, “One-pot tandem synthesis of a core - Shell brush copolymer from small molecule reactants by ring-opening metathesis and reversible addition-fragmentation chain transfer (co)polymerizations”, Macromolecules, 4, 2289-2292, 2007.
  • Y. You, C. Hong, W. Wang, W. Lu, and C. Y. Pan, “Preparation and characterization of thermally esponsive and biodegradable block copolymer comprised of PNIPAAM and PLA by combination of ROP and RAFT methods”, Macromolecules, 37, 9761-9797, 2004.
  • C. Chang, H. Wei, C. Y. Quan, Y. Y. Li, J. L iu, Z. C. Wang, S. X. Cheng, X. Z. Zhang, R. X. Zhuo, “Fabrication of thermosensitive PCL-PNIPAAm-PCL triblock copolymeric micelles for drug delivery”, J. Polym. Sci. Part A Polym. Chem. 46, 3048-3057, 2008.
  • P. J. Shi, Y. G. Li and C .Y. Pan, “Block and star block copolymers by mechanism transformation-X.Synthesis of poly(ethylene oxide) methyl ether/polystyrene/poly(L-lactide) ABC miktoarm star copolymers of by combination of RAFT and ROP”, Eur. Polym. J., 40, 1283-1290, 2004.
  • B. Luan, B. Q. Zhang, C. Y. Pan, “Synthesis and characterizations of well-defined branched polymers with AB(2) branches by combination of RAFT polymerization and ROP as well as ATRP”, J. Polym. Sci. Part A Polym. Chem., 44, 549-560, 2006.

One-pot PolimerleşmeYöntemiyle Poli(linoleik asit)-g-Poli(N-isopropilakrilamit)-g-Poli(D,L-laktid) Graft Kopolimerlerin Sentezi ve Karakterizasyonu

Year 2018, Volume: 6 Issue: 4, 1321 - 1334, 01.08.2018
https://doi.org/10.29130/dubited.434025

Abstract

Bu
çalışmada, Otookside polimerik linoleik asit peroksit (PLina)’nın halka açılma
polimerizasyonu ve serbest radikal polimerizasyonu bir arada kullanılarak tek
adımda (one-pot) üç bloklu graft kopolimerler sentezlendi. Poli(linoleik asit)-g-poli(N-isopropilakrilamit)-g-poli(D,L-laktid) yapısına sahip graft kopolimerler; PLina’nın ana
zincirinde bulunan peroksit grupları ile N-isopropilakrilamit
(NIPAM) monomeriyle serbest radikal polimerizasyonu ve
PLina’nın karboksilik
asit grupları ile D,L-laktid (LA) monomeri arasındaki halka açılma
polimerizasyonunun bir arada (one-pot) kullanılmasıyla sentezlendiler. One-pot polimerizasyon
reaksiyonuna etki eden polimerizasyon süresi, başlatıcı konsantrasyonu ve
monomer konsantrasyonu gibi temel parametreler incelendi. Elde edilen graft
kopolimerlerin karakterizasyonları 1H NMR ve GPC teknikleri
kullanılarak yapıldı. 

References

  • M. M. Reddy, S. Vivekannandhan, M. Misra, K. S. Bhatia and K. A. Mohanty Biobased, “plastics and bionanocomposites: Current statuse and future opportunities”, Progress in Polymer Science, 38, 1653-1689, 2013.
  • G. Lligadas, J. C. Ronda, M. Galia and V. Cadiz, “Renewable polymeric materials from vegetable oils: a perspective” Materials Today, 9, 2013.
  • W. B. Chieng, N. A. İbrahim, Y. Y. Then and Y. Y. Loo, “Epoxidized Vegetable Oils Plasticized Poly(lactic acid) Biocomposites: Mechanical, Thermal and Morphology Properties”, Molecules, 19, 16024-10638, 2014.
  • M. W. Gramlich, M. L. Robertson, and M. A. Hillmyer, “Reactive Compatibilization of Poly( L-lactid) and Conjugated Soybean Oil”, Macromolecules, 43, 2313-2321, 2010.
  • E. Kılıçay, B. Çakmaklı, B. Hazer, B. E. Denkbaş and B. Açıkgöz, “Acetylsalicylic(Acid Loading and Release Studies of the PMMA-g-Polymeric Oils/Oily Acids Micro and Nanospheres”, Journal of Applied Polymer Science, 3, 1610-1618, 2010.
  • B. Çakmaklı, B. Hazer, I. O. Tekin, S. Kızgut, M. Köksal, and Y. Menceloğlu, “Synthesis and characterization of polymeric linseed oil grafted methyl methacrylate or styrene”, Macromol. Biosci., 4, 649-655, 2004.
  • B. Çakmaklı, B. Hazer, . O. Tekin and F. B. Cömert, “Synthesis and characterization of polymeric soybean oil-g-methyl methacrylate (and n-butyl methacrylate) grafted copolymers: Biocompatibility and bacterial adhesion”, Biomacromolecules, 6, 1750-1758, 2005.
  • E. Keleş and B. Hazer, “Autooxidized Polyunsaturated Oil/Oily Acids: Post-it Application and Reaction with Fe(III) and Adhesion Properties” Macromolecular Symposia, 269,154-160, 2008.
  • A. Allı, and B Hazer, “Poly(N-isopropylacrylamide) thermoresponsive cross-linked conjugates containing polymeric soybean oil and/or polypropylene glycol”, Eur. Polym. Jour., 44, 1701-1713, 2008.
  • A. Allı, T. Şanal, B. Hazer, “Redox polymerization of N-isopropylacrylamide by using hydroxylated soya oil polymer”, Tur. Jour. Chem., 39, 382-394, 2015.
  • E. Kılıçay, B. Çakmaklı, B. Hazer, E. B. Denkbas, and B. Açıkgöz, “Acetylsalicylic acid loading and release studies of the PMMA-g-Poymeric oils/oily acids micro and nanospheres”, Journal of Applied Polymer Science, 119(3), 1610-1618, 2011.
  • A. Allı, S. Allı, C. R. Becer and B. Hazer, “One-pot synthesis of poly(linoleic acid)-g-poly (styrene)-g-poly(ε-caprolactone) graft copolymers”, J. Amer. Oil Chem. Soc. (JAOCS), 91, 849–858, 2014.
  • S. Allı, R. S. Aydın Tığlı,, A. Allı and B. Hazer, “Biodegradable Poly(ε-Caprolactone)- Based Graft Copolymers:Via Poly(Linoleic Acid): In Vitro Enzymatic Evaluation”, J. Amer. Oil. Chem. Soc., 92, 449-458, 2015.
  • A. Allı, S. Allı, C. R. Becer and B. Hazer, “Nitroxide mediated copolymerization of styrene and pentafluorostyrene initiated by polymeric linoleic acid”, European Journal of Lipid Science and Technology, 118 (2), 279-287, 2016.
  • A. Allı, Y. Arı and M. Gökçen, “Novel Poly(linolenic acid) Graft Copolymers: Synthesis, Characterization and Electrical Properties”, J. Am. Oil Chem. Soc., 93, 895–904, 2016.
  • T. Öztürk, M. Göktaş and B. Hazer, “One-Step Synthesis of Triarm Block Copolymers via Simultaneous Reversible-Addition Fragmentation Chain Transfer and Ring- Opening Polymerization”, J. Appl. Polym. Sci., 117, 1638–1645, 2010.
  • T. Öztürk, and İ. Cakmak ,“One-step synthesis of multiphase block copolymers via simultaneus free radical and ring opening polymerization using poly(ethylene oxide) possessing azo group”, J Macromol. Sci. Part A Pure and Appl. Chem., 45, 572–577. 2008.
  • M. Le Hellaye, C. Lefay, T.P. Davis, M. H. Stenzel and C. J. Barner-Kowollik. “Simultaneous reversible addition fragmentation chain transfer and ring-opening polymerization”,. J. Polym. Sci. Part A. Polym. Chem., 46: 3058-3067, 2008.
  • Y. C. Yu, G. Li, H. U. Kang and J. U. Youk , “One-step synthesis of poly(alkyl methacrylate)-b-polyester block copolymers via a dual initiator route combining RAFT polymerization and ROP”, Coll. Polym. Sci., 290: 1707-1712, 2012.
  • M. K. Mahanthappa, F. S. Bates and M. A. Hillmyer, “ Synthesis of ABA triblock copolymers by a tandem ROMP-RAFT strategy”, Macromolecules, 38:7890-7894, 2005.
  • H. Mori, S. Masuda and T. Endo, “Ring-opening copolymerization of 10-methylene-9,10 dihydroanthryl-9-spirophenylcyclopropane via free radical and RAFT processes”, Macromolecules, 41: 632–639, 2008.
  • D. H Han and C. Y. Pan, , “ Preparation and characterization of heteroarm H-shaped Terpolymers by combination of reversible addition-fragmentation transfer polymerization and ring-opening polymerization”, J. Polym. Sci. Part A Polym. Chem., 45, 789-799, 2007.
  • X. W. Xu and J. L. Huang, “Synthesis and characterization of amphiphilic copolymer of linear poly(ethylene oxide) linked with [poly(styrene-co-2-hydroxyethyl methacrylate)-graft-poly(epsilon-caprolactone)] using sequential controlled polymerization”, J. Polym. Sci. Part A. Polym. Chem., 44: 467-476, 2006.
  • J. Liu and C. Y. Pan, Synthesis and characterization of H-shaped copolymers by combination of RAFT polymerization and CROP”, Polymer, 46, 11133-11141, 2005.
  • J. Hong, Q. Wang, and Z. Fan, “Synthesis of multiblock polymer containing narrow polydispersity blocks”, Macromol. Rapid Commun., 27, 57-62, 2006.
  • C. Cheng, E. Khoshdel and K. L Wooley, “One-pot tandem synthesis of a core - Shell brush copolymer from small molecule reactants by ring-opening metathesis and reversible addition-fragmentation chain transfer (co)polymerizations”, Macromolecules, 4, 2289-2292, 2007.
  • Y. You, C. Hong, W. Wang, W. Lu, and C. Y. Pan, “Preparation and characterization of thermally esponsive and biodegradable block copolymer comprised of PNIPAAM and PLA by combination of ROP and RAFT methods”, Macromolecules, 37, 9761-9797, 2004.
  • C. Chang, H. Wei, C. Y. Quan, Y. Y. Li, J. L iu, Z. C. Wang, S. X. Cheng, X. Z. Zhang, R. X. Zhuo, “Fabrication of thermosensitive PCL-PNIPAAm-PCL triblock copolymeric micelles for drug delivery”, J. Polym. Sci. Part A Polym. Chem. 46, 3048-3057, 2008.
  • P. J. Shi, Y. G. Li and C .Y. Pan, “Block and star block copolymers by mechanism transformation-X.Synthesis of poly(ethylene oxide) methyl ether/polystyrene/poly(L-lactide) ABC miktoarm star copolymers of by combination of RAFT and ROP”, Eur. Polym. J., 40, 1283-1290, 2004.
  • B. Luan, B. Q. Zhang, C. Y. Pan, “Synthesis and characterizations of well-defined branched polymers with AB(2) branches by combination of RAFT polymerization and ROP as well as ATRP”, J. Polym. Sci. Part A Polym. Chem., 44, 549-560, 2006.
There are 30 citations in total.

Details

Primary Language Turkish
Subjects Engineering
Journal Section Articles
Authors

Sema Allı

Pinar Geçit This is me

Murat Gürel

Abdulkadir Allı

Publication Date August 1, 2018
Published in Issue Year 2018 Volume: 6 Issue: 4

Cite

APA Allı, S., Geçit, P., Gürel, M., Allı, A. (2018). One-pot PolimerleşmeYöntemiyle Poli(linoleik asit)-g-Poli(N-isopropilakrilamit)-g-Poli(D,L-laktid) Graft Kopolimerlerin Sentezi ve Karakterizasyonu. Duzce University Journal of Science and Technology, 6(4), 1321-1334. https://doi.org/10.29130/dubited.434025
AMA Allı S, Geçit P, Gürel M, Allı A. One-pot PolimerleşmeYöntemiyle Poli(linoleik asit)-g-Poli(N-isopropilakrilamit)-g-Poli(D,L-laktid) Graft Kopolimerlerin Sentezi ve Karakterizasyonu. DUBİTED. August 2018;6(4):1321-1334. doi:10.29130/dubited.434025
Chicago Allı, Sema, Pinar Geçit, Murat Gürel, and Abdulkadir Allı. “One-Pot PolimerleşmeYöntemiyle Poli(linoleik Asit)-G-Poli(N-Isopropilakrilamit)-G-Poli(D,L-Laktid) Graft Kopolimerlerin Sentezi Ve Karakterizasyonu”. Duzce University Journal of Science and Technology 6, no. 4 (August 2018): 1321-34. https://doi.org/10.29130/dubited.434025.
EndNote Allı S, Geçit P, Gürel M, Allı A (August 1, 2018) One-pot PolimerleşmeYöntemiyle Poli(linoleik asit)-g-Poli(N-isopropilakrilamit)-g-Poli(D,L-laktid) Graft Kopolimerlerin Sentezi ve Karakterizasyonu. Duzce University Journal of Science and Technology 6 4 1321–1334.
IEEE S. Allı, P. Geçit, M. Gürel, and A. Allı, “One-pot PolimerleşmeYöntemiyle Poli(linoleik asit)-g-Poli(N-isopropilakrilamit)-g-Poli(D,L-laktid) Graft Kopolimerlerin Sentezi ve Karakterizasyonu”, DUBİTED, vol. 6, no. 4, pp. 1321–1334, 2018, doi: 10.29130/dubited.434025.
ISNAD Allı, Sema et al. “One-Pot PolimerleşmeYöntemiyle Poli(linoleik Asit)-G-Poli(N-Isopropilakrilamit)-G-Poli(D,L-Laktid) Graft Kopolimerlerin Sentezi Ve Karakterizasyonu”. Duzce University Journal of Science and Technology 6/4 (August 2018), 1321-1334. https://doi.org/10.29130/dubited.434025.
JAMA Allı S, Geçit P, Gürel M, Allı A. One-pot PolimerleşmeYöntemiyle Poli(linoleik asit)-g-Poli(N-isopropilakrilamit)-g-Poli(D,L-laktid) Graft Kopolimerlerin Sentezi ve Karakterizasyonu. DUBİTED. 2018;6:1321–1334.
MLA Allı, Sema et al. “One-Pot PolimerleşmeYöntemiyle Poli(linoleik Asit)-G-Poli(N-Isopropilakrilamit)-G-Poli(D,L-Laktid) Graft Kopolimerlerin Sentezi Ve Karakterizasyonu”. Duzce University Journal of Science and Technology, vol. 6, no. 4, 2018, pp. 1321-34, doi:10.29130/dubited.434025.
Vancouver Allı S, Geçit P, Gürel M, Allı A. One-pot PolimerleşmeYöntemiyle Poli(linoleik asit)-g-Poli(N-isopropilakrilamit)-g-Poli(D,L-laktid) Graft Kopolimerlerin Sentezi ve Karakterizasyonu. DUBİTED. 2018;6(4):1321-34.