Synthesis of Methylol Fatty Alkyl Carbamates and Their Applications to Cotton

Abstract

Work on the idea of built-in lubrication has been extended to methylol fatty alkyl carbamates having structural similari ties with stearoyl ester of 1,3-dichloropropanol-2. A study of the conditions of methylolation of the fatty alkyl carbamates, their isolation, and characterization by ir spectra and nitrogen and formaldehyde contents leads to the conclusion that the isolated methylol derivatives exist as mixtures of mono-and dimethylol carbamate, the greater the alkyl substituent in the carbamate moiety, the greater is the formation of the monomethylol derivative. Reactivity of these methytol carbamates with cellulose in the collapsed state is poor, but is improved in the presence of free formaldehyde or formaldehyde donors such as acetals. Cotton fabric treated with methylol derivatives of octyl, lauryl, and stearyl carbamates shows improvement in flex abrasion resistance at a wrinkle recovery level of 210-240° (Shirley), maximum improvement being shown by methylol stearyl carbamate and acetal. Although the specific attachments of these compounds with cellulose are not known, the likelihood of alkyl chain attachment is high, as observed by the effects of chain length on mechanical properties of the treated fabric. The treated cotton also shows mild water repellency as well as resistance to microbial attack due to the presence of hydrophobic and toxophoric groups.