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Published in: Polymer Bulletin 11/2017

02-03-2017 | Original Paper

Poly(1,4-butadiene)-graft-poly(L-lactide) via the grafting-from strategy

Authors: Flavien Leroux, Véronique Montembault, Sandie Piogé, Sagrario Pascual, Laurent Fontaine

Published in: Polymer Bulletin | Issue 11/2017

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Abstract

Poly(1,4-butadiene)-graft-poly(L-lactide) copolymers were efficiently prepared via the grafting-from strategy using a combination of ring-opening metathesis polymerization (ROMP) of a hydroxyl-functionalized cyclobutene monomer and organocatalyzed ring-opening polymerization (ROP) of L-lactide. The copolymers were characterized by NMR, MALDI-TOF, SEC, TGA, and DSC demonstrating that well-defined polyester-grafted poly(1,4-butadiene) were obtained through the reported methodology.

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Appendix
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Literature
1.
go back to reference Hadjichristidis N, Pitsikalis M, Iatrou H, Driva P, Chatzichristidi M, Sakellariou G, Lohse D (2014) Graft copolymers. In: Mark HM (ed) Encyclopedia of polymer science and technology, 4th edn. Wiley, New York, pp 467–526 Hadjichristidis N, Pitsikalis M, Iatrou H, Driva P, Chatzichristidi M, Sakellariou G, Lohse D (2014) Graft copolymers. In: Mark HM (ed) Encyclopedia of polymer science and technology, 4th edn. Wiley, New York, pp 467–526
2.
go back to reference Hadjichristidis N, Iatrou H, Pitsikalis M, Mays J (2006) Macromolecular architectures by living and controlled/living polymerizations. Progr Polym Sci 31:1068–1132CrossRef Hadjichristidis N, Iatrou H, Pitsikalis M, Mays J (2006) Macromolecular architectures by living and controlled/living polymerizations. Progr Polym Sci 31:1068–1132CrossRef
3.
go back to reference Grubbs RH (2006) Olefin-metathesis catalysts for the preparation of molecules and materials (nobel lecture). Angew Chem Int Ed 45:3760–3765CrossRef Grubbs RH (2006) Olefin-metathesis catalysts for the preparation of molecules and materials (nobel lecture). Angew Chem Int Ed 45:3760–3765CrossRef
4.
go back to reference Grubbs RH, Khosravi E (2015) Polymer synthesis. Handbook of metathesis, vol 3, 2nd edn. Wiley-VCH, Weinheim Grubbs RH, Khosravi E (2015) Polymer synthesis. Handbook of metathesis, vol 3, 2nd edn. Wiley-VCH, Weinheim
5.
go back to reference Knall AC, Slugovc C (2014) Olefin metathesis polymerization. In: Grela K (ed) Olefin metathesis. Wiley, New York, pp 269–284CrossRef Knall AC, Slugovc C (2014) Olefin metathesis polymerization. In: Grela K (ed) Olefin metathesis. Wiley, New York, pp 269–284CrossRef
6.
go back to reference Le D, Morandi G, Legoupy S, Pascual S, Montembault V, Fontaine L (2013) Cyclobutenyl macromonomers: synthetic strategies and ring-opening metathesis polymerization. Eur Polym J 49:972–983CrossRef Le D, Morandi G, Legoupy S, Pascual S, Montembault V, Fontaine L (2013) Cyclobutenyl macromonomers: synthetic strategies and ring-opening metathesis polymerization. Eur Polym J 49:972–983CrossRef
7.
go back to reference Morandi G, Montembault V, Pascual S, Legoupy S, Fontaine L (2006) Well-defined graft copolymers issued from cyclobutenyl macromonomers by combination of ATRP and ROMP. Macromolecules 39:2732–2735CrossRef Morandi G, Montembault V, Pascual S, Legoupy S, Fontaine L (2006) Well-defined graft copolymers issued from cyclobutenyl macromonomers by combination of ATRP and ROMP. Macromolecules 39:2732–2735CrossRef
8.
go back to reference Leroux F, Montembault V, Pascual S, Guerin W, Guillaume SM, Fontaine L (2014) Synthesis and polymerization of cyclobutenyl-functionalized polylactide and polycaprolactone: a consecutive ROP/ROMP route to poly(1,4-butadiene)-g-polyesters. Polym Chem 5:3476–3486CrossRef Leroux F, Montembault V, Pascual S, Guerin W, Guillaume SM, Fontaine L (2014) Synthesis and polymerization of cyclobutenyl-functionalized polylactide and polycaprolactone: a consecutive ROP/ROMP route to poly(1,4-butadiene)-g-polyesters. Polym Chem 5:3476–3486CrossRef
9.
go back to reference Morandi G, Pascual S, Montembault V, Legoupy S, Delorme N, Fontaine L (2009) Synthesis of brush copolymers based on a poly(1,4-butadiene) backbone via the “grafting from” approach by ROMP and ATRP. Macromolecules 42:6927–6931CrossRef Morandi G, Pascual S, Montembault V, Legoupy S, Delorme N, Fontaine L (2009) Synthesis of brush copolymers based on a poly(1,4-butadiene) backbone via the “grafting from” approach by ROMP and ATRP. Macromolecules 42:6927–6931CrossRef
10.
go back to reference Leroux F, Montembault V, Piogé S, Pascual S, Brotons G, Fontaine L (2016) High molar mass poly(1,4-butadiene)-graft-poly(ε-caprolactone) copolymers by ROMP: synthesis via the grafting-from route and self-assembling properties. Macromolecules 49:4739–4745CrossRef Leroux F, Montembault V, Piogé S, Pascual S, Brotons G, Fontaine L (2016) High molar mass poly(1,4-butadiene)-graft-poly(ε-caprolactone) copolymers by ROMP: synthesis via the grafting-from route and self-assembling properties. Macromolecules 49:4739–4745CrossRef
11.
go back to reference Pensec S, Leroy M, Akkouche H, Spassky N (2000) Stereocomplex formation in enantiomeric diblock and triblock copolymers of poly(ε-caprolactone) and polylactide. Polym Bull 45:373–380CrossRef Pensec S, Leroy M, Akkouche H, Spassky N (2000) Stereocomplex formation in enantiomeric diblock and triblock copolymers of poly(ε-caprolactone) and polylactide. Polym Bull 45:373–380CrossRef
12.
go back to reference Tsuji H (2005) Poly(lactide) stereocomplexes: formation, structure, properties, degradation, and applications. Macromol Biosci 5:569–597CrossRef Tsuji H (2005) Poly(lactide) stereocomplexes: formation, structure, properties, degradation, and applications. Macromol Biosci 5:569–597CrossRef
13.
go back to reference Jha S, Dutta S, Bowden NB (2004) Synthesis of ultralarge molecular weight bottlebrush polymers using Grubbs’ catalysts. Macromolecules 37:4365–4374CrossRef Jha S, Dutta S, Bowden NB (2004) Synthesis of ultralarge molecular weight bottlebrush polymers using Grubbs’ catalysts. Macromolecules 37:4365–4374CrossRef
14.
go back to reference Zhang K, Tew GN (2012) Cyclic brush polymers by combining ring-expansion metathesis polymerization and the “grafting from” technique. ACS Macro Lett 1:574–579CrossRef Zhang K, Tew GN (2012) Cyclic brush polymers by combining ring-expansion metathesis polymerization and the “grafting from” technique. ACS Macro Lett 1:574–579CrossRef
15.
go back to reference Yoo J, Runge MB, Bowden NB (2011) Synthesis of complex architectures of comb block copolymers. Polymer 52:2499–2504CrossRef Yoo J, Runge MB, Bowden NB (2011) Synthesis of complex architectures of comb block copolymers. Polymer 52:2499–2504CrossRef
16.
go back to reference Jing F, Hillmyer MA (2008) A bifunctional monomer derived from lactide for toughening polylactide. J Am Chem Soc 130:13826–13827CrossRef Jing F, Hillmyer MA (2008) A bifunctional monomer derived from lactide for toughening polylactide. J Am Chem Soc 130:13826–13827CrossRef
17.
go back to reference Theryo G, Jing F, Pitet LM, Hillmyer MA (2010) Tough polylactide graft copolymers. Macromolecules 43:7394–7397CrossRef Theryo G, Jing F, Pitet LM, Hillmyer MA (2010) Tough polylactide graft copolymers. Macromolecules 43:7394–7397CrossRef
18.
go back to reference Lohmeijer BGG, Pratt RC, Leibfarth F, Logan JW, Long DA, Dove AP, Nederberg F, Choi J, Wade C, Waymouth RM, Hedrick JL (2006) Guanidine and amidine organocatalysts for ring-opening polymerization of cyclic esters. Macromolecules 39:8574–8583CrossRef Lohmeijer BGG, Pratt RC, Leibfarth F, Logan JW, Long DA, Dove AP, Nederberg F, Choi J, Wade C, Waymouth RM, Hedrick JL (2006) Guanidine and amidine organocatalysts for ring-opening polymerization of cyclic esters. Macromolecules 39:8574–8583CrossRef
19.
go back to reference Pratt RC, Lohmeijer BGG, Long DA, Waymouth RM, Hedrick JL (2006) Triazabicyclodecene: a simple bifunctional organocatalyst for acyl transfer and ring-opening polymerization of cyclic esters. J Am Chem Soc 128:4556–4557CrossRef Pratt RC, Lohmeijer BGG, Long DA, Waymouth RM, Hedrick JL (2006) Triazabicyclodecene: a simple bifunctional organocatalyst for acyl transfer and ring-opening polymerization of cyclic esters. J Am Chem Soc 128:4556–4557CrossRef
20.
go back to reference Penczek S, Szymanski R, Duda A, Baran J (2003) Living polymerization of cyclic esters—a route to (bio)degradable polymers. Influence of chain transfer to polymer on livingness. Macromol Symp 201:261–269CrossRef Penczek S, Szymanski R, Duda A, Baran J (2003) Living polymerization of cyclic esters—a route to (bio)degradable polymers. Influence of chain transfer to polymer on livingness. Macromol Symp 201:261–269CrossRef
21.
go back to reference Li A, Li Z, Zhang S, Sun G, Policarpio DM, Wooley KL (2012) Synthesis and direct visualization of dumbbell-shaped molecular brushes. ACS Macro Lett 1:241–245CrossRef Li A, Li Z, Zhang S, Sun G, Policarpio DM, Wooley KL (2012) Synthesis and direct visualization of dumbbell-shaped molecular brushes. ACS Macro Lett 1:241–245CrossRef
22.
go back to reference Kang EH, Lee IH, Choi TL (2012) Brush polymers containing semiconducting polyene backbones: graft-through synthesis via cyclopolymerization and conformational analysis on the coil-to-rod transition. ACS Macro Lett 1:1098–1102CrossRef Kang EH, Lee IH, Choi TL (2012) Brush polymers containing semiconducting polyene backbones: graft-through synthesis via cyclopolymerization and conformational analysis on the coil-to-rod transition. ACS Macro Lett 1:1098–1102CrossRef
23.
go back to reference Yasuniwa M, Tsubakihara S, Sugimoto Y, Nakafuku C (2004) Thermal analysis of the double-melting behavior of poly(L-lactic acid). J Polym Sci Part B: Polym Phys 42:25–32CrossRef Yasuniwa M, Tsubakihara S, Sugimoto Y, Nakafuku C (2004) Thermal analysis of the double-melting behavior of poly(L-lactic acid). J Polym Sci Part B: Polym Phys 42:25–32CrossRef
24.
go back to reference Pyda M, Bopp RC, Wunderlich B (2004) Heat capacity of poly(lactic acid). J Chem Thermodyn 36:731–742CrossRef Pyda M, Bopp RC, Wunderlich B (2004) Heat capacity of poly(lactic acid). J Chem Thermodyn 36:731–742CrossRef
25.
go back to reference Sveinbjörnsson BR, Miyake GM, El-Batta A, Grubbs RH (2014) Stereocomplex formation of densely grafted brush polymers. ACS Macro Lett 3:26–29CrossRef Sveinbjörnsson BR, Miyake GM, El-Batta A, Grubbs RH (2014) Stereocomplex formation of densely grafted brush polymers. ACS Macro Lett 3:26–29CrossRef
26.
go back to reference Oh S, Lee JK, Theato P, Char K (2008) Nanoporous thin films based on polylactide-grafted norbornene copolymers. Chem Mater 20:6974–6984CrossRef Oh S, Lee JK, Theato P, Char K (2008) Nanoporous thin films based on polylactide-grafted norbornene copolymers. Chem Mater 20:6974–6984CrossRef
Metadata
Title
Poly(1,4-butadiene)-graft-poly(L-lactide) via the grafting-from strategy
Authors
Flavien Leroux
Véronique Montembault
Sandie Piogé
Sagrario Pascual
Laurent Fontaine
Publication date
02-03-2017
Publisher
Springer Berlin Heidelberg
Published in
Polymer Bulletin / Issue 11/2017
Print ISSN: 0170-0839
Electronic ISSN: 1436-2449
DOI
https://doi.org/10.1007/s00289-017-1961-y

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