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Polymer Bulletin
Published in: Polymer Bulletin 9/2014

01-09-2014 | Original Paper

Partially biobased polyamphiphile-bearing reactive epoxy groups in the side chains and its application to the hydrogel

Authors: Hisatoyo Morinaga, Yoshihide Kiyokawa, Ryosuke Fujikawa, Daisuke Nagai, Hiroshi Morikawa

Published in: Polymer Bulletin | Issue 9/2014

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Abstract

Partially biobased polyamphiphile-bearing reactive epoxy groups in the side chains were obtained in 62–78 % yields by a radical copolymerization of limonene oxide (LO) and PEG methylacrylate (PEGA) with different feed ratios. Degree of LO incorporation into the copolymer was determined as 12–23 % by 1H NMR spectroscopic analysis. The copolymer having LO unit:PEGA unit = 19:81 formed polymer associates in water, particle diameter of which was ranged mainly from 4 to 66 nm and hydrodynamic mean diameter was 12.3 nm. Its critical micelle concentration was determined as 0.53 g/L by fluorescence spectroscopic analysis. A cross-linking reaction of the epoxy groups in the side chains was conducted with 3.97 mol% (to the epoxy group) of branched poly(ethylene imine) as a cross-linker to give the corresponding hydrogel in 56 % yield. The hydrogel can absorb water as much as 13 times its own mass.
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Appendix
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Literature
1.
Gandini A (2008) Polymers from renewable resources: a challenge for the future of macromolecular materials. Macromolecules 41(24):9491–9504CrossRef
2.
Mathers RT (2012) How well can renewable resources mimic commodity monomers and polymers? J Polym Sci, Part A: Polym Chem 50:1–15CrossRef
3.
Zhao J, Schlaad H (2013) Synthesis of terpene-based polymers. Adv Polym Sci 253:151–190
4.
Tschan MJL, Brulé E, Haquette P, Thomas CM (2012) Synthesis of biodegradable polymers from renewable resources. Polym Chem 3:836–851CrossRef
5.
Marín FR, Soler-Rivas C, Benavente-García O, Castillo J, Pérez-Alvarez JA (2007) By-products from different citrus processes as a source of customized functional fibres. Food Chem 100(2):736–741CrossRef
6.
Lan-Phi NT, Shimamura T, Ukeda H, Sawamura M (2009) Chemical and aroma profiles of yuzu (Citrus junos) peel oils of different cultivars. Food Chem 115:1042–1047CrossRef
7.
Terada A, Kitajima N, Machmudah S, Tanaka M, Sasaki M, Goto M (2010) Cold-pressed yuzu oil fractionation using countercurrent supercritical CO2 extraction column. Sep Pur Tech 71:107–113CrossRef
8.
Oliveira P, Rojas-Cervantes ML, Ramos AM, Fonseca IM, do Rego Botelho AM, Vital J (2006) Limonene oxidation over V2O5/TiO2 catalysts. Catal Today 118:307–314CrossRef
9.
Yadav JS, Reddy BVS, Baishya G (2002) InCl3-catalyzed highly regioselective ring opening of epoxides with thiols. Chem Lett 31(9):906–907CrossRef
10.
Morinaga H, Kiyokawa Y, Kataoka M, Masuda J, Nagai D (2013) Synthesis of partially biobased polymer-bearing reactive epoxy groups in the side chains by radical copolymerization of limonene oxide with methyl acrylate. Polym Bull 70:1113–1123CrossRef
11.
Kimura Y (2009) Molecular, structural, and material design of bio-based polymers. Polym J 41:797–807CrossRef
12.
John G, Vemula PK (2006) Design and development of soft nanomaterials from biobased amphiphiles. Soft Matter 2:909–914CrossRef
13.
Vemula PK, John G (2008) Crops: a green approach toward self-assembled soft materials. Acc Chem Res 41(6):769–782CrossRef
14.
de Oliveira HFN, Felisberti MI (2013) Amphiphilic copolymers of sucrose methacrylate and acrylic monomers: bio-based materials from renewable resource. Carbohydr Polym 94(1):317–322CrossRef
15.
Morishima Y, Aota H, Saegusa K, Kamachi M (1996) Long-lived porphyrin cation radicals protected in unimer micelles of hydrophobically-modified polyelectrolytes. Macromolecules 29:6505–6509CrossRef
16.
Yamamoto H, Mizusaki M, Yoda K, Morishima Y (1998) Fluorescence studies of hydrophobic association of random copolymers of sodium 2-(acrylamido)-2-methylpropanesulfonate and N-dodecylmethacrylamide in water. Macromolecules 31:3588–3594CrossRef
17.
Yusa S, Hashidzume A, Morishima Y (1999) Interpolymer association of cholesterol pendants linked to a polyelectrolyte as studied by quasielastic light scattering and fluorescence techniques. Langmuir 15:8826–8831CrossRef
18.
Yusa S, Kamachi M, Morishima Y (2000) Self-association of cholesterol-end-capped poly(sodium 2-(acrylamido)-2-methylpropanesulfonate) in aqueous solution. Macromolecules 33:1224–1231CrossRef
19.
Noda T, Hashizume A, Morishima Y (2000) Micelle formation of random copolymers of sodium 2-(acrylamido)-2-methylpropanesulfonate and a nonionic surfactant macromonomer in water as studied by fluorescence and dynamic light scattering. Macromolecules 33:3694–3704CrossRef
20.
Hashidzume A, Kurokawa M, Morishima Y, Kamachi M (2002) Synthesis of amphiphilic block copolymers of 4-substituted styrene and cyclohexane oxide utilizing radical/cation transformation polymerization. Macromolecules 35:5326–5330CrossRef
21.
Yusa S, Sakakibara A, Yamamoto T, Morishima Y (2002) Reversible pH-induced formation and disruption of unimolecular micelles of an amphiphilic polyelectrolyte. Macromolecules 35:5243–5249CrossRef
22.
Suzuki N, Morishima Y, Arimori S, Endo T (2007) Preparation of polystyrene nanoparticles by seed polymerization using amphiphilic random copolymer micelles as seeds. Polym J 39:187–191CrossRef
23.
Satoh K, Matsuda M, Nagai K, Kamigaito M (2010) AAB-sequence living radical chain copolymerization of naturally occurring limonene with maleimide: an end-to-end sequence-regulated copolymer. J Am Chem Soc 132:10003–10005CrossRef
24.
Sharma S, Srivastava AK (2003) Alternating copolymers of limonene with methyl methacrylate: kinetics and mechanism. J Macromol Sci Part A Pure Appl Chem 40:593–603CrossRef
25.
Vorobyova O, Yekta A, Winnik MA (1998) Fluorescent probe studies of the association in an aqueous solution of a hydrophobically modified poly (ethylene oxide). Macromolecules 31:8998–9007CrossRef
26.
Wilhelm M, Zhao CL, Wang Y, Xu R, Winnik MA, Mura JL, Riess G, Groucher MD (1991) Poly(styrene-ethylene oxide) block copolymer micelle formation in water: a fluorescence probe study. Macromolecules 24:1033–1040CrossRef
27.
Kumacheva E, Rharbi Y, Winnik MA, Guo L, Tam KC, Jenkins RD (1997) Fluorescence studies of an alkaline swellable associative polymer in aqueous solution. Langmuir 13:182–186CrossRef
28.
Horiuchi K, Rharbi Y, Spiro JG, Yekta A, Winnik MA, Jenkins RD (1999) Fluorescence probe studies of hydrophobic domains in a model hydrophobically modified alkali-swellable emulsion (HASE) polymer with C20H41 groups. Langmuir 15:1644–1650CrossRef
29.
Lutz JF, Akdemir Ö, Hoth A (2006) Point by point comparison of two thermosensitive polymers exhibiting a similar LCST: is the age of poly(NIPAM) over? J Am Chem Soc 128:13046–13047CrossRef
30.
Magnusson J, Khan A, Pasparakis G, Saeed A, Wang W, Alexander C (2008) Ion-sensitive “isothermal” responsive polymers prepared in water. J Am Chem Soc 130:10852–10853CrossRef
31.
Morinaga H, Morikawa H, Wang Y, Sudo A, Endo T (2009) Amphiphilic copolymer having acid-labile acetal in the side chain as a hydrophobe: controlled release of aldehyde by thermo-responsive aggregation–dissociation of polymer micelles. Macromolecules 42:2229–2235CrossRef
Metadata
Title
Partially biobased polyamphiphile-bearing reactive epoxy groups in the side chains and its application to the hydrogel
Authors
Hisatoyo Morinaga
Yoshihide Kiyokawa
Ryosuke Fujikawa
Daisuke Nagai
Hiroshi Morikawa
Publication date
01-09-2014
Publisher
Springer Berlin Heidelberg
Published in
Polymer Bulletin / Issue 9/2014
Print ISSN: 0170-0839
Electronic ISSN: 1436-2449
DOI
https://doi.org/10.1007/s00289-014-1199-x

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