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Erschienen in: Cellulose 6/2014

01.12.2014 | Original Paper

Functionalization of cellulose with epoxy groups via γ-initiated RAFT-mediated grafting of glycidyl methacrylate

verfasst von: Murat Barsbay, Yasko Kodama, Olgun Güven

Erschienen in: Cellulose | Ausgabe 6/2014

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Abstract

Glycidyl methacrylate (GMA), was grafted from cellulose by the combination of radiation-induced initiation and the reversible addition-fragmentation chain transfer (RAFT) polymerization technique, leading to epoxy functionalized surfaces that enable further modifications. Cumyl dithiobenzoate and 2-cyanoprop-2-yl dithiobenzoate were employed as the RAFT agents. The effects of absorbed dose, monomer and RAFT agent concentrations and solvent choice on grafting yield were investigated. Characterization of the synthesized copolymers by ATR-FTIR spectroscopy, X-ray photoelectron spectroscopy, scanning electron microscopy, thermal analysis and contact angle measurements revealed the grafting of poly(glycidyl methacrylate) (PGMA) from cellulose. Size-exclusion chromatography analysis indicated the difficulty of controlling the polymerization of GMA due to branching and/or crosslinking reactions that might occur in PGMA structure under γ-radiation.

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Literatur
Zurück zum Zitat Ahmad S, Zulfiqar S (2002) Synthesis, characterization and thermal degradation of glycidyl methacrylate-a-methyl styrene copolymers. Polym Degrad Stab 76:173–177CrossRef Ahmad S, Zulfiqar S (2002) Synthesis, characterization and thermal degradation of glycidyl methacrylate-a-methyl styrene copolymers. Polym Degrad Stab 76:173–177CrossRef
Zurück zum Zitat Bannister I, Billingham NC, Armes SP, Rannard SP, Findlay P (2006) Development of branching in living radical copolymerization of vinyl and divinyl monomers. Macromolecules 39:7483–7492CrossRef Bannister I, Billingham NC, Armes SP, Rannard SP, Findlay P (2006) Development of branching in living radical copolymerization of vinyl and divinyl monomers. Macromolecules 39:7483–7492CrossRef
Zurück zum Zitat Barner L, Zwaneveld N, Perera S, Pham Y, Davis TP (2002) Reversible addition–fragmentation chain-transfer graft polymerization of styrene: solid phases for organic and peptide synthesis. J Polym Sci A Polym Chem 40:4180–4192CrossRef Barner L, Zwaneveld N, Perera S, Pham Y, Davis TP (2002) Reversible addition–fragmentation chain-transfer graft polymerization of styrene: solid phases for organic and peptide synthesis. J Polym Sci A Polym Chem 40:4180–4192CrossRef
Zurück zum Zitat Barner L, Quinn JF, Barner-Kowollik C, Vana P, Davis TP (2003) Reversible addition–fragmentation chain transfer polymerization initiated with γ-radiation at ambient temperature: an overview. Eur Polym J 39:449–459CrossRef Barner L, Quinn JF, Barner-Kowollik C, Vana P, Davis TP (2003) Reversible addition–fragmentation chain transfer polymerization initiated with γ-radiation at ambient temperature: an overview. Eur Polym J 39:449–459CrossRef
Zurück zum Zitat Barner-Kowollik C, Vana P, Quinn JF, Davis TP (2002) Long-lived intermediates in reversible addition-fragmentation chain-transfer (RAFT) polymerization generated by γ-radiation. J Polym Sci A Polym Chem 40:1058–1063CrossRef Barner-Kowollik C, Vana P, Quinn JF, Davis TP (2002) Long-lived intermediates in reversible addition-fragmentation chain-transfer (RAFT) polymerization generated by γ-radiation. J Polym Sci A Polym Chem 40:1058–1063CrossRef
Zurück zum Zitat Barsbay M, Güven O (2009) A short review of radiation-induced raft-mediated graft copolymerization: a powerful combination for modifying the surface properties of polymers in a controlled manner. Radiat Phys Chem 78:1054–1059CrossRef Barsbay M, Güven O (2009) A short review of radiation-induced raft-mediated graft copolymerization: a powerful combination for modifying the surface properties of polymers in a controlled manner. Radiat Phys Chem 78:1054–1059CrossRef
Zurück zum Zitat Barsbay M, Güven O (2013) RAFT mediated grafting of poly(acrylic acid) (PAA) from polyethylene/polypropylene (PE/PP) nonwoven fabric via preirradiation. Polymer 54:4838–4848CrossRef Barsbay M, Güven O (2013) RAFT mediated grafting of poly(acrylic acid) (PAA) from polyethylene/polypropylene (PE/PP) nonwoven fabric via preirradiation. Polymer 54:4838–4848CrossRef
Zurück zum Zitat Barsbay M, Güven O, Stenzel MH, Davis TP, Barner-Kowollik C, Barner L (2007) Verification of controlled grafting of styrene from cellulose via radiation-induced RAFT polymerization. Macromolecules 40:7140–7147CrossRef Barsbay M, Güven O, Stenzel MH, Davis TP, Barner-Kowollik C, Barner L (2007) Verification of controlled grafting of styrene from cellulose via radiation-induced RAFT polymerization. Macromolecules 40:7140–7147CrossRef
Zurück zum Zitat Barsbay M, Güven O, Davis TP, Barner-Kowollik C, Barner L (2009) RAFT-mediated polymerization and grafting of sodium 4-styrene sulfonate from cellulose initiated via γ-radiation. Polymer 50:973–982CrossRef Barsbay M, Güven O, Davis TP, Barner-Kowollik C, Barner L (2009) RAFT-mediated polymerization and grafting of sodium 4-styrene sulfonate from cellulose initiated via γ-radiation. Polymer 50:973–982CrossRef
Zurück zum Zitat Barsbay M, Güven O, Bessbousse H, Wade TL, Beuneu F, Clochard M-C (2013) Nanopore size tuning of polymeric membranes using the raft-mediated radical polymerization. J Membr Sci 445:135–145CrossRef Barsbay M, Güven O, Bessbousse H, Wade TL, Beuneu F, Clochard M-C (2013) Nanopore size tuning of polymeric membranes using the raft-mediated radical polymerization. J Membr Sci 445:135–145CrossRef
Zurück zum Zitat Beecher JF, Frihart CR (2005) X-ray photoelectron spectroscopy for characterization of wood surfaces in adhesion studies. In: Frihart CR (ed) Wood adhesives 2005. Forest Products Society, San Diego, ISBN: 1892529459, pp 83–89 Beecher JF, Frihart CR (2005) X-ray photoelectron spectroscopy for characterization of wood surfaces in adhesion studies. In: Frihart CR (ed) Wood adhesives 2005. Forest Products Society, San Diego, ISBN: 1892529459, pp 83–89
Zurück zum Zitat Bhattacharya A, Misra BN (2004) Grafting: a versatile means to modify polymers: techniques, factors and applications. Prog Polym Sci 29:767–814CrossRef Bhattacharya A, Misra BN (2004) Grafting: a versatile means to modify polymers: techniques, factors and applications. Prog Polym Sci 29:767–814CrossRef
Zurück zum Zitat Brandrup J, Immergut EH (1989) Polymer handbook, 3rd edn. Wiley, New York, p VII/15 Brandrup J, Immergut EH (1989) Polymer handbook, 3rd edn. Wiley, New York, p VII/15
Zurück zum Zitat Carlmark A (2013) Tailoring cellulose surfaces by controlled polymerization methods. Macromol Chem Phys 214:1539–1544CrossRef Carlmark A (2013) Tailoring cellulose surfaces by controlled polymerization methods. Macromol Chem Phys 214:1539–1544CrossRef
Zurück zum Zitat Dilli S, Garnett JL (1967) Radiation-induced reactions with cellulose. III. Kinetics of styrene copolymerization in methanol. J Appl Polym Sci 11:859–870CrossRef Dilli S, Garnett JL (1967) Radiation-induced reactions with cellulose. III. Kinetics of styrene copolymerization in methanol. J Appl Polym Sci 11:859–870CrossRef
Zurück zum Zitat Dureault A, Gnanou Y, Taton D, Destarac M, Leising F (2003) Reaction of cyclic tetrathiophosphates with carboxylic acids as a means to generate dithioesters and control radical polymerization by RAFT. Angew Chem Int Ed 42:2869–2872CrossRef Dureault A, Gnanou Y, Taton D, Destarac M, Leising F (2003) Reaction of cyclic tetrathiophosphates with carboxylic acids as a means to generate dithioesters and control radical polymerization by RAFT. Angew Chem Int Ed 42:2869–2872CrossRef
Zurück zum Zitat Freire CSR, Silvestre AJD, Pascoal NC, Gandini A, Fardim P, Holmbom B (2006) Surface characterization by XPS, contact angle measurements and ToF-SIMS of cellulose fibers partially esterified with fatty acids. J Colloid Interface Sci 301:205–209CrossRef Freire CSR, Silvestre AJD, Pascoal NC, Gandini A, Fardim P, Holmbom B (2006) Surface characterization by XPS, contact angle measurements and ToF-SIMS of cellulose fibers partially esterified with fatty acids. J Colloid Interface Sci 301:205–209CrossRef
Zurück zum Zitat Gao H, Matyjaszewski K (2009) Synthesis of functional polymers with controlled architecture by CRP of monomers in the presence of cross-linkers: from stars to gels. Prog Polym Sci 34:317–350CrossRef Gao H, Matyjaszewski K (2009) Synthesis of functional polymers with controlled architecture by CRP of monomers in the presence of cross-linkers: from stars to gels. Prog Polym Sci 34:317–350CrossRef
Zurück zum Zitat Gao H, Min K, Matyjaszewski K (2007) Determination of gel point during atom transfer radical copolymerization with cross-linker. Macromolecules 40:7763–7770CrossRef Gao H, Min K, Matyjaszewski K (2007) Determination of gel point during atom transfer radical copolymerization with cross-linker. Macromolecules 40:7763–7770CrossRef
Zurück zum Zitat Gudipati CS, Tan MBH, Hussain H, Liu Y, He C, Davis TP (2008) Synthesis of poly(glycidyl methacrylate)-block- poly(pentafluorostyrene) by RAFT: precursor to novel amphiphilic poly(glyceryl methacrylate)-block-poly(pentafluorostyrene). Macromol Rapid Commun 29:1902–1907CrossRef Gudipati CS, Tan MBH, Hussain H, Liu Y, He C, Davis TP (2008) Synthesis of poly(glycidyl methacrylate)-block- poly(pentafluorostyrene) by RAFT: precursor to novel amphiphilic poly(glyceryl methacrylate)-block-poly(pentafluorostyrene). Macromol Rapid Commun 29:1902–1907CrossRef
Zurück zum Zitat Han DH, Pan CY (2006) A novel strategy to synthesize double comb-shaped water soluble copolymer by RAFT polymerization. Macromol Chem Phys 207:836–843CrossRef Han DH, Pan CY (2006) A novel strategy to synthesize double comb-shaped water soluble copolymer by RAFT polymerization. Macromol Chem Phys 207:836–843CrossRef
Zurück zum Zitat Hua DB, Bai W, Xiao J, Bai RK, Lu W, Pan CY (2005) A strategy for synthesis of azide polymers via controlled/living free radical copolymerization of allyl azide under 60Co γ-ray irradiation. Chem Mater 17:4574–4576CrossRef Hua DB, Bai W, Xiao J, Bai RK, Lu W, Pan CY (2005) A strategy for synthesis of azide polymers via controlled/living free radical copolymerization of allyl azide under 60Co γ-ray irradiation. Chem Mater 17:4574–4576CrossRef
Zurück zum Zitat Hutchinson RA, Beuermann S, Paquet DA Jr, McMinn JH, Jackson C (1998) Determination of free-radical propagation rate coefficients for cycloalkyl and functional methacrylates by pulsed-laser polymerization. Macromolecules 31:1542–1547CrossRef Hutchinson RA, Beuermann S, Paquet DA Jr, McMinn JH, Jackson C (1998) Determination of free-radical propagation rate coefficients for cycloalkyl and functional methacrylates by pulsed-laser polymerization. Macromolecules 31:1542–1547CrossRef
Zurück zum Zitat Ide N, Fukuda T (1997) Nitroxide-controlled free-radical copolymerization of vinyl and divinyl monomers. Evaluation of pendant-vinyl reactivity. Macromolecules 30:4268–4271CrossRef Ide N, Fukuda T (1997) Nitroxide-controlled free-radical copolymerization of vinyl and divinyl monomers. Evaluation of pendant-vinyl reactivity. Macromolecules 30:4268–4271CrossRef
Zurück zum Zitat Ide N, Fukuda T (1999) Nitroxide-controlled free-radical copolymeriza- tion of vinyl and divinyl monomers. 2. Gelation. Macromolecules 32:95–99CrossRef Ide N, Fukuda T (1999) Nitroxide-controlled free-radical copolymeriza- tion of vinyl and divinyl monomers. 2. Gelation. Macromolecules 32:95–99CrossRef
Zurück zum Zitat Isaure F, Cormack PAG, Graham S, Sherrington DC, Armes SP, Buetuen V (2004) Synthesis of branched poly(methyl methacrylate)s via controlled/living polymerisations exploiting ethylene glycol dimethacrylate as branching agent. Chem Commun 9:1138–1139 Isaure F, Cormack PAG, Graham S, Sherrington DC, Armes SP, Buetuen V (2004) Synthesis of branched poly(methyl methacrylate)s via controlled/living polymerisations exploiting ethylene glycol dimethacrylate as branching agent. Chem Commun 9:1138–1139
Zurück zum Zitat Jun L, Min Y, Jiuqiang L, Hongfei H (2001) Preirradiation grafting polymerization of DMAEMA onto cotton cellulose fabrics. J App Polym Sci 81:3578–3581CrossRef Jun L, Min Y, Jiuqiang L, Hongfei H (2001) Preirradiation grafting polymerization of DMAEMA onto cotton cellulose fabrics. J App Polym Sci 81:3578–3581CrossRef
Zurück zum Zitat Kato K, Uchida E, Kang E-T, Uyama Y, Ikada Y (2003) Polymer surface with graft chains. Progres Polym Sci 28:209–259CrossRef Kato K, Uchida E, Kang E-T, Uyama Y, Ikada Y (2003) Polymer surface with graft chains. Progres Polym Sci 28:209–259CrossRef
Zurück zum Zitat Klemm D, Heublein B, Fink H-P, Bohn A (2005) Cellulose: fascinating biopolymer and sustainable raw material. Angew Chem Int Ed 44:3358–3393CrossRef Klemm D, Heublein B, Fink H-P, Bohn A (2005) Cellulose: fascinating biopolymer and sustainable raw material. Angew Chem Int Ed 44:3358–3393CrossRef
Zurück zum Zitat Kodama Y, Barsbay M, Güven O (2014) Radiation-induced and RAFT-mediated grafting of poly(hydroxyethyl methacrylate) (PHEMA) from cellulose surfaces. Radiat Phys Chem 94:98–104CrossRef Kodama Y, Barsbay M, Güven O (2014) Radiation-induced and RAFT-mediated grafting of poly(hydroxyethyl methacrylate) (PHEMA) from cellulose surfaces. Radiat Phys Chem 94:98–104CrossRef
Zurück zum Zitat Krassig HA (1993) Cellulose—structure, accessibility and reactivity. In: Huglin MB (ed) Polymer monographs, vol 11. Gordon and Breach Science Publishers, Yverdon Krassig HA (1993) Cellulose—structure, accessibility and reactivity. In: Huglin MB (ed) Polymer monographs, vol 11. Gordon and Breach Science Publishers, Yverdon
Zurück zum Zitat Labet M, Thielemans W (2011) Improving the reproducibility of chemical reactions on the surface of cellulose nanocrystals: ROP of e-caprolactone as a case study. Cellulose 18:607–617CrossRef Labet M, Thielemans W (2011) Improving the reproducibility of chemical reactions on the surface of cellulose nanocrystals: ROP of e-caprolactone as a case study. Cellulose 18:607–617CrossRef
Zurück zum Zitat Laricheva VP (2008) Effect of ionizing radiation on epoxy oligomers of different structures and manufacture of new promising materials on their base. Radiat Phys Chem 77:29–33CrossRef Laricheva VP (2008) Effect of ionizing radiation on epoxy oligomers of different structures and manufacture of new promising materials on their base. Radiat Phys Chem 77:29–33CrossRef
Zurück zum Zitat Lindqvist J, Nyström D, Östmark E, Antoni P, Carlmark A, Johansson M, Hult A, Malmström E (2008) Intelligent dual-responsive cellulose surfaces via surface-initiated ATRP. Biomacromolecules 9:2139–2145CrossRef Lindqvist J, Nyström D, Östmark E, Antoni P, Carlmark A, Johansson M, Hult A, Malmström E (2008) Intelligent dual-responsive cellulose surfaces via surface-initiated ATRP. Biomacromolecules 9:2139–2145CrossRef
Zurück zum Zitat Liu B, Kazlauciunas A, Guthrie JT, Perrier S (2005) One-pot hyperbranched polymer synthesis mediated by reversible addition fragmentation chain transfer (RAFT) polymerization. Macromolecules 38:2131–2136CrossRef Liu B, Kazlauciunas A, Guthrie JT, Perrier S (2005) One-pot hyperbranched polymer synthesis mediated by reversible addition fragmentation chain transfer (RAFT) polymerization. Macromolecules 38:2131–2136CrossRef
Zurück zum Zitat Malmström E, Carlmark A (2012) Controlled grafting of cellulose fibres—an outlook beyond paper and cardboard. Polym Chem 3:1702–1713CrossRef Malmström E, Carlmark A (2012) Controlled grafting of cellulose fibres—an outlook beyond paper and cardboard. Polym Chem 3:1702–1713CrossRef
Zurück zum Zitat Morandia G, Thielemans W (2012) Synthesis of cellulose nanocrystals bearing photocleavable grafts by ATRP. Polym Chem 3:1402–1407CrossRef Morandia G, Thielemans W (2012) Synthesis of cellulose nanocrystals bearing photocleavable grafts by ATRP. Polym Chem 3:1402–1407CrossRef
Zurück zum Zitat Nasef MM, Güven O (2012) Radiation-grafted copolymers for separation and purification purposes: status, challenges and future directions. Prog Polym Sci 37:1597–1656CrossRef Nasef MM, Güven O (2012) Radiation-grafted copolymers for separation and purification purposes: status, challenges and future directions. Prog Polym Sci 37:1597–1656CrossRef
Zurück zum Zitat Roa-Luna M, Jaramillo-Soto G, Castañeda-Flores PV, Vivaldo-Lima E (2010) Copolymerization kinetics of styrene and divinylbenzene in the presence of S-thiobenzoyl thioglycolic acid as RAFT agent. Chem Eng Technol 33:1893–1899CrossRef Roa-Luna M, Jaramillo-Soto G, Castañeda-Flores PV, Vivaldo-Lima E (2010) Copolymerization kinetics of styrene and divinylbenzene in the presence of S-thiobenzoyl thioglycolic acid as RAFT agent. Chem Eng Technol 33:1893–1899CrossRef
Zurück zum Zitat Taton D, Baussard J-F, Dupayage L, Poly J, Gnanou Y, Ponsinet V (2006) Water soluble polymeric nanogels by xanthate-mediated radical crosslinking copolymerization. Chem Commun 18:1953–1955 Taton D, Baussard J-F, Dupayage L, Poly J, Gnanou Y, Ponsinet V (2006) Water soluble polymeric nanogels by xanthate-mediated radical crosslinking copolymerization. Chem Commun 18:1953–1955
Zurück zum Zitat Thakur VK, Thakur MK, Gupta RK (2013) Graft copolymers from cellulose: synthesis, characterization and evaluation. Carbohydr Polym 14:18–25CrossRef Thakur VK, Thakur MK, Gupta RK (2013) Graft copolymers from cellulose: synthesis, characterization and evaluation. Carbohydr Polym 14:18–25CrossRef
Zurück zum Zitat Vo C-D, Rosselgong J, Armes SP, Billingham NC (2007) RAFT synthesis of branched acrylic copolymers. Macromolecules 40:7119–7125CrossRef Vo C-D, Rosselgong J, Armes SP, Billingham NC (2007) RAFT synthesis of branched acrylic copolymers. Macromolecules 40:7119–7125CrossRef
Zurück zum Zitat Yu Q, Zeng F, Zhu S (2001) Atom transfer radical polymerization of poly(ethylene glycol) dimethacrylate. Macromolecules 34:1612–1618CrossRef Yu Q, Zeng F, Zhu S (2001) Atom transfer radical polymerization of poly(ethylene glycol) dimethacrylate. Macromolecules 34:1612–1618CrossRef
Zurück zum Zitat Zhao P, Yan Y, Feng X, Liu L, Wang C, Chen Y (2012) Highly efficient synthesis of polymer brushes with PEO and PCL as side chains via click chemistry. Polymer 53:1992–2000CrossRef Zhao P, Yan Y, Feng X, Liu L, Wang C, Chen Y (2012) Highly efficient synthesis of polymer brushes with PEO and PCL as side chains via click chemistry. Polymer 53:1992–2000CrossRef
Zurück zum Zitat Zhu J, Zhou D, Zhu X, Chen G (2004) Reversible addition–fragmentation chain transfer polymerization of glycidyl methacrylate with 2-cyanoprop-2-yl 1-dithionaphthalate as a chain-transfer agent. J Polym Sci, Part A: Polym Chem 42:2558–2565CrossRef Zhu J, Zhou D, Zhu X, Chen G (2004) Reversible addition–fragmentation chain transfer polymerization of glycidyl methacrylate with 2-cyanoprop-2-yl 1-dithionaphthalate as a chain-transfer agent. J Polym Sci, Part A: Polym Chem 42:2558–2565CrossRef
Metadaten
Titel
Functionalization of cellulose with epoxy groups via γ-initiated RAFT-mediated grafting of glycidyl methacrylate
verfasst von
Murat Barsbay
Yasko Kodama
Olgun Güven
Publikationsdatum
01.12.2014
Verlag
Springer Netherlands
Erschienen in
Cellulose / Ausgabe 6/2014
Print ISSN: 0969-0239
Elektronische ISSN: 1572-882X
DOI
https://doi.org/10.1007/s10570-014-0416-y

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