Synthesis and crystallization-induced microphase separation of cellulose triacetate-block-poly(γ-benzyl-l-glutamate)

Kamitakahara, Hiroshi; Baba, A. Ramesha; Yoshinaga, Arata; Suhara, Ryo; Takano, Toshiyuki

doi:10.1007/s10570-014-0383-3

Cited by 10 publications

(8 citation statements)

References 56 publications

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“…To improve the mechanical properties of cellulose acetate without compromising their biodegradability, we herein focus on the use of PCL as a soft blend partner because of its softness and high biodegradability. , Some researchers have already reported on the modification of the mechanical properties of cellulose acetate by blending it with PCL. − Thus, a BCP consisting of cellulose acetate and PCL is a promising candidate as an environmentally benign compatibilizer. However, the design and synthesis of cellulose-derivative-based BCPs still face some major challenges; in fact, only a handful of examples of cellulose-based BCPs have been reported so far. − This might be due to the difficulty in preparing functionalized cellulosic building blocks for conjugation with synthetic polymer segments. Moreover, compatibilizer performance is known to be closely related to the BCP architecture. − Thus, a facile and modular synthesis approach is essential to identify a suitable cellulose derivative-based BCP as a compatibilizer.…”

Section: Introductionmentioning

confidence: 99%

Acetyl Cellooligosaccharide-Based Block Copolymers for Toughening Cellulose Triacetate/Poly(ε-caprolactone) Biodegradable Blends

Katsuhara,

Tsuji,

Sunagawa

et al. 2024

ACS Sustainable Chem. Eng.

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Although brittle, cellulose acetate is a highly promising next-generation environmentally benign material. However, toughening it without deteriorating its biodegradability is challenging. This study reports on the design and synthesis of a block copolymer (BCP) comprising cellooligosaccharide triacetate and poly(ε-caprolactone) (PCL) as a compatibilizer for the cellulose triacetate (CTA) and PCL blend. PCL is an ideal blend partner due to its softness and biodegradability. BCPs with different architectures such as AB, ABA, and A 2 BA 2 types (A, cellooligosaccharide triacetate; B, PCL) were prepared by Cucatalyzed azido-alkyne click reactions of azido-functionalized PCLs and propargyl-functionalized cellooligosaccharide triacetate. CTA/ PCL/BCP ternary blend films were prepared by solvent casting, followed by hot pressing. These films had better mechanical properties than those of neat-CTA and CTA/PCL binary blend films. ABA-and A 2 BA 2 -type BCPs were particularly effective, probably because they could form a loop structure of the PCL block in the PCL domain, leading to improved stability at the interface. Atomic force microscopy revealed that the improved interfacial adhesion between the CTA matrix and PCL domain mediated by BCPs is the dominant factor for improving mechanical performance, rather than improving the dispersion of the PCL domain. Our study results may help in expanding the potential applications of cellulose acetate without compromising its biodegradability.

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Section: Introductionmentioning

confidence: 99%

Acetyl Cellooligosaccharide-Based Block Copolymers for Toughening Cellulose Triacetate/Poly(ε-caprolactone) Biodegradable Blends

Katsuhara,

Tsuji,

Sunagawa

et al. 2024

ACS Sustainable Chem. Eng.

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“…In recent decades, "click chemistry" methods have been developed that share attractive features (e.g., rapid kinetics, mild conditions, high efficiency, high yield) and some have been applied to polysaccharides [4]. Azide-alkyne Huisgen cycloaddition [5], olefin cross-metathesis [6][7][8], and the thiol-ene reaction [9,10], are among those reported to have been applied to polysaccharides [6,11,12], affording a broad range of pathways for designing bioconjugates.…”

Section: Introductionmentioning

confidence: 99%

A Versatile Method for Preparing Polysaccharide Conjugates via Thiol-Michael Addition

Chen

Edgar

2021

Polymers

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Polysaccharide conjugates are important renewable materials. If properly designed, they may for example be able to carry drugs, be proactive (e.g., with amino acid substituents) and can carry a charge. These aspects can be particularly useful for biomedical applications. Herein, we report a simple approach to preparing polysaccharide conjugates. Thiol-Michael additions can be mild, modular, and efficient, making them useful tools for post-modification and the tailoring of polysaccharide architecture. In this study, hydroxypropyl cellulose (HPC) and dextran (Dex) were modified by methacrylation. The resulting polysaccharide, bearing α,β-unsaturated esters with tunable DS (methacrylate), was reacted with various thiols, including 2-thioethylamine, cysteine, and thiol functional quaternary ammonium salt through thiol-Michael addition, affording functionalized conjugates. This click-like synthetic approach provided several advantages including a fast reaction rate, high conversion, and the use of water as a solvent. Among these polysaccharide conjugates, the ones bearing quaternary ammonium salts exhibited competitive antimicrobial performance, as supported by a minimum inhibitory concentration (MIC) study and tracked by SEM characterization. Overall, this methodology provides a versatile route to polysaccharide conjugates with diverse functionalities, enabling applications such as antimicrobial activity, gene or drug delivery, and biomimicry.

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“…However, polysaccharide-derivative-blockoligosaccharides (Breitenbach et al 2017;de Medeiros Modolon et al 2012) or polysaccharide-derivative-block-oligopeptides have not received much attention from researchers. Carbohydrate-based block copolymers with polyester (Fajardo et al 2014;Liu and Zhang 2007), poly(methyl methacrylate) (Dax et al 2013;Togashi et al 2014), poly(styrene) (Loos and Müller 2002;Otsuka et al 2013;Yagi et al 2010), poly(N-isopropylacrylamide) (Dax et al 2013;Otsuka et al 2012), poly(γ-benzyl-L-glutamate) (Kamitakahara et al 2014), and poly(3hexylthiophene) (Sakai-Otsuka et al 2017) polyisoprene (Hung et al 2017), and poly(ethyleneoxide) (Akiyoshi et al 1999) have been reported. Shoichet and her colleagues focused on a physical blend of hyaluronan and methylcellulose covalently linked to peptides for tissue-engineering purposes (Parker et al 2016).…”

Section: Introductionmentioning

confidence: 99%

Methylcelluloses end-functionalized with peptides as thermoresponsive supramolecular hydrogelators

et al. 2018

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This paper describes the synthesis of methylcelluloses endfunctionalized with peptides and an investigation into their functions. We found that aqueous solutions of methylcellulose end-functionalized not only with carbohydrates but also with peptide segments, such as di(arginine) and di(glutamic acid), behave as thermoresponsive supramolecular hydrogelators at human-body temperature. The slow drug release from thermoresponsive hydrogels of methylcelluloses end-functionalized with peptides is attributed to ionic interactions between model drugs and peptide segments in these hydrogels. Reactions of methylated cellobiose with di(arginine) and di(glutamic acid) were used to determine optimum reaction conditions for the synthesis of methylcelluloses end-functionalized with these peptide residues). The surface activities, zeta potentials, thermal properties, hydrogelation behavior, and cytotoxicities of these peptide-functionalized methylcelluloses are also discussed. Highlights: • Methylcelluloses end-functionalized with peptides were synthesized. • Peptides-end-functionalized methylcelluloses behave as thermoresponsive supramolecular hydrogelators at human-body temperature. • The slow drug release from thermoresponsive hydrogels of methylcelluloses end-functionalized with peptides was achieved.

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Synthesis and crystallization-induced microphase separation of cellulose triacetate-block-poly(γ-benzyl-l-glutamate)

Cited by 10 publications

References 56 publications

Acetyl Cellooligosaccharide-Based Block Copolymers for Toughening Cellulose Triacetate/Poly(ε-caprolactone) Biodegradable Blends

Acetyl Cellooligosaccharide-Based Block Copolymers for Toughening Cellulose Triacetate/Poly(ε-caprolactone) Biodegradable Blends

A Versatile Method for Preparing Polysaccharide Conjugates via Thiol-Michael Addition

Methylcelluloses end-functionalized with peptides as thermoresponsive supramolecular hydrogelators

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