Studies on chitosan: 2. Solution stability and reactivity of partially N-acetylated chitosan derivatives in aqueous media.
The stability of the solutions of partially N-acetylated chitosans was studied by two methods: (1) 1% solutions of the chitosan derivatives in 0.1 M aqueous acetic acid were added dropwise to buffer solutions with pH from 8.6 to 12 and to a 0.1 M NaOH solution; (2) to each 0.5% solution of the derivatives in 0.1 M acetic acid was added the desired amount of a 1 M NaOH solution. The stability data obtained were summarized with respect to the degree of N-acetylation. It was found that the solutions of the derivatives with more than 50% acetyl content were stable even in alkaline conditions and the gelation and precipitation of the solutions did not occur. The reactivity of the derivatives with the degree of N-acetylation of more than 50% was studied using methyl 4-azidobenzoimidate (MABI) and ethylene glycol diglycidyl ether in homogeneous states. It was found that MABI reacted with amino groups of the chitosans only at neutral pH and glycidyl groups reacted at neutral and alkaline pH. It seems that these unique properties of chitosans with a degree of N-acetylation of more than 50% will enable us to prepare new chitosan derivatives.
Aiba
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Biomimetic Chemistry Division, Industrial Products Research Institute, Ibaraki, Japan.
D000107:Acetylation; D001386:Azides / Q000494:pharmacology; D002686:Chitin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D048271:Chitosan; D005026:Ethylene Glycols / Q000494:pharmacology; D005782:Gels; D006863:Hydrogen-Ion Concentration; D007096:Imidoesters / Q000494:pharmacology; D012972:Sodium Hydroxide; D012995:Solubility; D012996:Solutions
D001386:Azides; D005026:Ethylene Glycols; D005782:Gels; D007096:Imidoesters; D012996:Solutions; D002686:Chitin; D012972:Sodium Hydroxide; C026810:methyl 4-azidobenzimidate; D048271:Chitosan