New class of carbohydrate-based nonionic surfactants: diblock co-oligomers of tri-O-methylated and unmodified cello-oligosaccharides

• Published in: Cellulose (London) Vol. 14; no. 5; pp. 513 - 528
• Main Authors: Kamitakahara, Hiroshi, Nakatsubo, Fumiaki, Klemm, Dieter
• Format: Journal Article
• Language: English
• Published: Dordrecht Dordrecht : Springer Netherlands 01.10.2007; Springer Nature B.V
• Subjects: Carbohydrates; Cello-oligosaccharides; Diblock co-oligomer; methylcellulose; Nonionic surfactant; Oligomers; Oligosaccharides; Surfactants; Trimers
• ISSN: 0969-0239; 1572-882X
• DOI: 10.1007/s10570-007-9128-x

Mixtures of diblock co-oligomers of tri-O-methylated and unmodified cello-oligosaccharides have been found to be amphiphilic, as reported before. In order to clarify their accurate amphiphilic property, diblock co-oligomers of tri-O-methylated and unmodified cello-oligosaccharides with monodispersity, methyl β-d-glucopyranosyl-(1[rightward arrow]4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1[rightward arrow]4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1[rightward arrow]4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1[rightward arrow]4)-2,3,6-tri-O-methyl-d-glucopyranoside (1, pentamer), methyl β-d-glucopyranosyl-(1[rightward arrow]4)- β-d-glucopyranosyl-(1[rightward arrow]4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1[rightward arrow]4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1[rightward arrow]4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1[rightward arrow]4)-2,3,6-tri-O-methyl-d-glucopyranoside (2, hexamer), and methyl β-d-glucopyranosyl-(1[rightward arrow]4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1[rightward arrow]4)- 2,3,6-tri-O-methyl-d-glucopyranoside (3, trimer) were synthesized independently. These compounds had higher surface activities compared to the mixture of diblock co-oligomers of tri-O-methylated and unmodified cello-oligosaccharides and commercially available methylcellulose (MC) SM-4. This paper describes the methods of synthesis of these compounds, and the influence of amphiphilic character on their surface activity. A new class of carbohydrate-based nonionic surfactant without long alkyl chain was discovered.