Structural Components in Methyl Vinyl Sulfone Modified Cotton Cellulose

Abstract

IZBSTRACTRIethyIsulfon~~lethyl cellulose was prepared a t a low degree of substitution (O.11), wh~ch 1s conventional for the chemical mod~fication of cotton, by the hlIichael addition of methyl vinyl sulfone to cotton fabrlc. The distrib~ition of substituents i n the anhydroglucose units was determined by hydrolysis of the molecular chain to glucose units, selective concentration of the substituted glucose components, gas-liquid chromatographic analyses of the inethylsulfonylethylgl~rcoses, and comparison with authentic salnples of 2-0-, 3-0-, and 6-0-~nethylsulfonyl-ethylglucoses in the form of trimethylsilyl ether,. The validity of each of these steps for quantitative analyses has been examined. The ratio of the 2-0-, 3-0-, and 6-0-~nonometh~.lsulfonylethylgl~lco~ei \bas found to be 0 20:0.03.1.0. S o evidence was found for the presence of di-or tri-substituted gl~lcoses.

One-Step “Click” Method for Generating Vinyl Sulfone Groups on Hydroxyl-Containing Water-Soluble Polymers

“…Being an active nucleophile, it can form a covalent linkage with the electrophilic double bond of VS by 1,4-nucleophilic conjugate addition (Michael-type addition). 20 Balazs and co-workers, as well as other groups, 21,22 have utilized this reaction to cross-link HA with DVS. In these reports, the molar ratio of DVS to OH is low (e.g., 1:4) such that both VS groups of each DVS react with OH groups of HA and cross-link the HA chains.…”

Reagent effects on distribution of methylsulfonylethyl substituents in the D-glucopyranosyl unit of cotton cellulose

“…Hydrolysis of Metlzylsulfotyletliyl Cellirloses nrrrl Estinlntiorr of Distr.iblrtio11 of Substitctetlts One-gram samples of methylsulfonylethyl celluloses were dissolved in sulfuric acid (15 g, 72%, 25-30", 8 h) and hydrolyzed in subsequent dilutions (to 7.7 N, 25-30", 16-20 h, and 1.5 N, reflux, 6 h) under an atmosphere of nitrogen (6). The acid was neutralized with barium hydroxide and the filtrate was freeze-dried to a solid mixture of glucose and 0-methylsulfonylethyl-D-glucopyranoses.…”

“…Trimethylsilyl ethers (20) of the dry hydrolyzates were prepared and analyzed for the ratio of the 2-0-, 3-0-, and 6-0-mono(methylsulfonylethyl)-D-glucopyranoses by gas-liquid chromatography on QF-1 columns: isothermal at 200" and 30 psig on column b; isothermal at 218" and 40 psig on column c. These procedures have been described in detail in an earlier publication (6). Results (Table I) of ratios of peak areas from triangulation or from the product of peak height and retention time were identical for the two columns.…”

Mono-O-(methylsulfonylethy)-d-glucoses

“…Chromatograms (1,10,13). The retention times are expressed in minutes, and the relative retention times, tr, are often referred to the second peak of the 6-0-(methylsulfonylethy1)-D-glucose, which is assigned a value of unity.…”