Preparation and characterization of cellulose derivatives by regioseleclive esterification of biodegradable cyclic esters

Ayaka Mayumi, Takuya Kttaoka, Hiroyuki Wariishi

研究成果: ジャーナルへの寄稿Conference article

抄録

New cellulose derivatives were prepared by the regioselective derivatization of cellulose with L-lactide (LA) and ε-caprolactone (CL) in a lithium chloride/N, N-dimethylacetamide solvent system, and investigated for their characteristics by spectroscopic analyses, calorimetry, solvent solubility/enzymatic degradability tests. Fourier transform Raman spectra of cellulose derivatives confirmed that the LA and CL molecules were covalently introduced into cellulose at the hydroxyl groups through the ring-opening esterification catalyzed by LiCl. The 13C nuclear magnetic resonance analysis indicated that the ring-opened LA and CL were regioselectively combined with cellulose C6-OH. Moreover, LA and CL portions were partially grafted on the cellulose backbone, like a comb-shaped architecture. Both cellulose derivatives were highly soluble in dimethyl-sulfoxide available for material forming. A part of cellulose-LA was swollen or soluble in water, while cellulose-CL had poor affinity for water. The solvent solubility depended on the introduced amounts of cyclic esters. Enzymatic degradation of cellulose derivatives immediately occurred by the cellulase treatment even under the mild conditions that commercial cellulose diacetate could not be hydrolyzed. The cellulose derivatives also showed thermodynamic characteristics. Thus, the cellulose derivatives prepared in this study are expected as a biomass-based eco-material in practical applications.

元の言語英語
ページ(範囲)257-261
ページ数5
ジャーナルAppita Annual Conference
3
出版物ステータス出版済み - 12 1 2005
イベント59th Appita Annual Conference and Exhibition, incorporating the 13th ISWFPC: International Symposium on Wood, Fibre and Pulping Chemistry - Auckland, ニュージ―ランド
継続期間: 5 16 20055 19 2005

Fingerprint

Cellulose derivatives
Esterification
ester
cellulose
Cellulose
Esters
Solubility
Dimethyl sulfoxide
Calorimetry
solubility
Raman scattering
Water
Fourier transforms
Biomass
Lithium
Nuclear magnetic resonance
Thermodynamics
Degradation
Molecules
calorimetry

All Science Journal Classification (ASJC) codes

  • Media Technology

これを引用

Preparation and characterization of cellulose derivatives by regioseleclive esterification of biodegradable cyclic esters. / Mayumi, Ayaka; Kttaoka, Takuya; Wariishi, Hiroyuki.

:: Appita Annual Conference, 巻 3, 01.12.2005, p. 257-261.

研究成果: ジャーナルへの寄稿Conference article

@article{0cda69f840da4e809c29868bb4a90f51,
title = "Preparation and characterization of cellulose derivatives by regioseleclive esterification of biodegradable cyclic esters",
abstract = "New cellulose derivatives were prepared by the regioselective derivatization of cellulose with L-lactide (LA) and ε-caprolactone (CL) in a lithium chloride/N, N-dimethylacetamide solvent system, and investigated for their characteristics by spectroscopic analyses, calorimetry, solvent solubility/enzymatic degradability tests. Fourier transform Raman spectra of cellulose derivatives confirmed that the LA and CL molecules were covalently introduced into cellulose at the hydroxyl groups through the ring-opening esterification catalyzed by LiCl. The 13C nuclear magnetic resonance analysis indicated that the ring-opened LA and CL were regioselectively combined with cellulose C6-OH. Moreover, LA and CL portions were partially grafted on the cellulose backbone, like a comb-shaped architecture. Both cellulose derivatives were highly soluble in dimethyl-sulfoxide available for material forming. A part of cellulose-LA was swollen or soluble in water, while cellulose-CL had poor affinity for water. The solvent solubility depended on the introduced amounts of cyclic esters. Enzymatic degradation of cellulose derivatives immediately occurred by the cellulase treatment even under the mild conditions that commercial cellulose diacetate could not be hydrolyzed. The cellulose derivatives also showed thermodynamic characteristics. Thus, the cellulose derivatives prepared in this study are expected as a biomass-based eco-material in practical applications.",
author = "Ayaka Mayumi and Takuya Kttaoka and Hiroyuki Wariishi",
year = "2005",
month = "12",
day = "1",
language = "English",
volume = "3",
pages = "257--261",
journal = "Appita Annual Conference",
issn = "1443-5454",
publisher = "Appita Inc.",

}

TY - JOUR

T1 - Preparation and characterization of cellulose derivatives by regioseleclive esterification of biodegradable cyclic esters

AU - Mayumi, Ayaka

AU - Kttaoka, Takuya

AU - Wariishi, Hiroyuki

PY - 2005/12/1

Y1 - 2005/12/1

N2 - New cellulose derivatives were prepared by the regioselective derivatization of cellulose with L-lactide (LA) and ε-caprolactone (CL) in a lithium chloride/N, N-dimethylacetamide solvent system, and investigated for their characteristics by spectroscopic analyses, calorimetry, solvent solubility/enzymatic degradability tests. Fourier transform Raman spectra of cellulose derivatives confirmed that the LA and CL molecules were covalently introduced into cellulose at the hydroxyl groups through the ring-opening esterification catalyzed by LiCl. The 13C nuclear magnetic resonance analysis indicated that the ring-opened LA and CL were regioselectively combined with cellulose C6-OH. Moreover, LA and CL portions were partially grafted on the cellulose backbone, like a comb-shaped architecture. Both cellulose derivatives were highly soluble in dimethyl-sulfoxide available for material forming. A part of cellulose-LA was swollen or soluble in water, while cellulose-CL had poor affinity for water. The solvent solubility depended on the introduced amounts of cyclic esters. Enzymatic degradation of cellulose derivatives immediately occurred by the cellulase treatment even under the mild conditions that commercial cellulose diacetate could not be hydrolyzed. The cellulose derivatives also showed thermodynamic characteristics. Thus, the cellulose derivatives prepared in this study are expected as a biomass-based eco-material in practical applications.

AB - New cellulose derivatives were prepared by the regioselective derivatization of cellulose with L-lactide (LA) and ε-caprolactone (CL) in a lithium chloride/N, N-dimethylacetamide solvent system, and investigated for their characteristics by spectroscopic analyses, calorimetry, solvent solubility/enzymatic degradability tests. Fourier transform Raman spectra of cellulose derivatives confirmed that the LA and CL molecules were covalently introduced into cellulose at the hydroxyl groups through the ring-opening esterification catalyzed by LiCl. The 13C nuclear magnetic resonance analysis indicated that the ring-opened LA and CL were regioselectively combined with cellulose C6-OH. Moreover, LA and CL portions were partially grafted on the cellulose backbone, like a comb-shaped architecture. Both cellulose derivatives were highly soluble in dimethyl-sulfoxide available for material forming. A part of cellulose-LA was swollen or soluble in water, while cellulose-CL had poor affinity for water. The solvent solubility depended on the introduced amounts of cyclic esters. Enzymatic degradation of cellulose derivatives immediately occurred by the cellulase treatment even under the mild conditions that commercial cellulose diacetate could not be hydrolyzed. The cellulose derivatives also showed thermodynamic characteristics. Thus, the cellulose derivatives prepared in this study are expected as a biomass-based eco-material in practical applications.

UR - http://www.scopus.com/inward/record.url?scp=29344472828&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=29344472828&partnerID=8YFLogxK

M3 - Conference article

AN - SCOPUS:29344472828

VL - 3

SP - 257

EP - 261

JO - Appita Annual Conference

JF - Appita Annual Conference

SN - 1443-5454

ER -