Graft polymerization of 1,2-butylene oxide from cellulose in ionic liquid/N-methyl-2-pyrrolidone solvent

Kadokawa, Jun‐ichi; Minami, Yukine; Anai, Tomoya; Hara, Hitomi; Yamamoto, Katsuhiro

doi:10.1007/s00289-022-04467-w

Cited by 2 publications

(1 citation statement)

References 31 publications

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“…In the past decade, the concept of a “circular economy” has become increasingly important in materials development. − In particular, upcycling to produce high-value-added materials from biomass is essential for building a sustainable society based on resource recycling. − The utilization of biomass, a renewable organic material, is broadly classified into two methods: one uses the biomass extracted from plants as it is, and the other decomposes biomass to an appropriate state for use. For example, cellulose nanofibers and cellulose nanocrystals extracted from wood are used to make highly functional films, fibers, and porous materials by combining them with other materials due to the functionality derived from their structures. − In contrast, since cellulose can be decomposed to a usable state with a fine structure through saccharification and fermentation, much research is being conducted to convert cellulose into useful chemicals, such as ethanol, which is a biofuel. , In addition to research on biomass already in use, discovering methods for unutilized biomass will become increasingly attractive and essential for developing future materials to promote a sustainable society.…”

Section: Introductionmentioning

confidence: 99%

Melanin Upcycling: Creation of Polymeric Materials from Melanin Decomposition Products

Morita,

Matsuura,

Izawa

et al. 2024

ACS Sustainable Chem. Eng.

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Melanin is a widely occurring biopolymer and has been the subject of much research, especially in dermatology. However, from a resource perspective, melanin is still an unutilized biomass because of its complex three-dimensional cross-linked structure, which makes it challenging to handle. Here, we demonstrate melanin upcycling by decomposing melanin and preparing polymeric materials from its products. A detailed study of the chemical decomposition products of artificial melanin, i.e., polydopamine, reveals that the melanin decomposition products are mainly oligomeric pyrrole derivatives containing carboxylic acids. Furthermore, decomposition experiments using natural melanin extracted from cuttlefish ink revealed that the composition of melanin decomposition products is almost identical regardless of the melanin source. We proposed a melanin decomposition mechanism and demonstrated the preparation of biobased polymer films and particles from melanin decomposition products. The use of melanin decomposition products as building blocks for material preparation is expected to lead to the development of new biodegradable polymers from biomass.

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Section: Introductionmentioning

confidence: 99%

Melanin Upcycling: Creation of Polymeric Materials from Melanin Decomposition Products

Morita,

Matsuura,

Izawa

et al. 2024

ACS Sustainable Chem. Eng.

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Synthesis of Amorphous Cellulose Derivatives via Michael Addition to Hydroxyalkyl Acrylates for Thermoplastic Film Applications

Nagaishi,

Totani,

Kadokawa

2024

Polymers

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The aim of this study is to prepare new cellulose derivatives that show good feasibility and processability. Accordingly, in this study, we demonstrate Michael addition to hydroxyalkyl acrylates, that is, 2-hydroxyethyl and 4-hydroxybutyl acrylates (HEA and HBA, respectively), to synthesize amorphous cellulose derivatives under alkaline conditions. The reactions were carried out in the presence of LiOH in ionic liquid (1-butyl-2,3-dimethylimidazolium chloride)/N,N-dimethylformamide (DMF) solvents at room temperature or 50 °C for 1 h. The Fourier transform infrared and 1H nuclear magnetic resonance (NMR) measurements of the products supported the progress of Michael addition; however, the degrees of substitution (DS) were not high (0.3–0.6 for HEA and 0.6 for HBA). The powder X-ray diffraction analysis of the products indicated their amorphous nature. The cellulosic Michael adduct from HEA with DS = 0.6 was swollen with high polar organic liquids, such as DMF. In addition to swelling with these liquids, the cellulosic Michael adduct from HBA was soluble in dimethyl sulfoxide (DMSO), leading to its 1H NMR analysis in DMSO-d6. This adduct was found to form a cast film with flexible properties from its DMSO solutions. Furthermore, films containing an ionic liquid, 1-butyl-3-methylimidazolium chloride, showed thermoplasticity. The Michael addition approach to hydroxyalkyl acrylates is quite effective to totally reduce crystallinity, leading to good feasibility and processability in cellulosic materials, even with low DS. In addition, the present thermoplastic films will be applied in practical, bio-based, and eco-friendly fields.

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Graft polymerization of 1,2-butylene oxide from cellulose in ionic liquid/N-methyl-2-pyrrolidone solvent

Cited by 2 publications

References 31 publications

Melanin Upcycling: Creation of Polymeric Materials from Melanin Decomposition Products

Melanin Upcycling: Creation of Polymeric Materials from Melanin Decomposition Products

Synthesis of Amorphous Cellulose Derivatives via Michael Addition to Hydroxyalkyl Acrylates for Thermoplastic Film Applications

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