Long alkyl chains (C 12 ) have been introduced onto glucuronoxylan and its sulfoethyl derivative via O-alkylation using 1-bromododecane in dimethylsulfoxide. The new amphiphilic xylan derivatives were characterized by chemical, elemental, and spectral analyses. They reduce the surface tension and exhibit remarkable emulsifying and protein foam-stabilizing properties. The results indicate that the development of new biopolymeric surfactants may be based on heteroxylans that are abundant in hardwoods and annual plants, and represent an unexploited renewable polysaccharide resource.
Summary: Water‐soluble, partially hydrophobized derivatives of O‐(carboxymethyl)cellulose (CMC) were prepared by esterification of CMC in its ‘gel suspension’ form. The classical esterification method (A) using stearoyl chloride/pyridine as well as two unconventional methods based on reaction with mixed anhydrides (B) and transesterification with vinyl laurate (C) respectively, were compared in terms of the structural, molecular and performance properties of the obtained derivatives. The classical esterification and method B yielded water‐soluble simple fatty acid esters, whereas mixed acetic‐fatty acid esters were obtained by method C. In all cases, molecular degradation of CMC was observed. 1H and 13C NMR spectroscopy of the acetyl‐lauroyl derivatives of CMC with a degree of esterification DSE of 0.20 indicated a prevalence of the lauroyl groups (DSAc:DSLa = 0.03:0.17). Most of the water‐soluble derivatives exhibited excellent emulsifying efficiency. They represent polysaccharide‐based surfactants with effective anti‐redeposition properties as well as good washing power. Suitable derivatives can be prepared under mild reaction conditions by both unconventional methods which implies that they have potential as substitutes for the expensive and invasive conventional method.Preparation of CMC derivatives.magnified imagePreparation of CMC derivatives.
The synthesis of water‐soluble octenylsuccinates of carboxymethyl starch (OS‐CMS) was performed with octenylsuccinic anhydride by assistance of microwave and ultrasound irradiation using the dimethyl sulphoxide/p‐toluenesulphonic acid system and DMSO as solvents for activation of CMS as well as reaction medium of the following esterification. The prepared OS‐CMS derivatives were characterized with regard to their structural, surface‐active and performance properties. The application of both microwave and ultrasound irradiation as energy sources permitted to shorten the esterification time to several minutes from 24 h of the previously reported conventional heating [33], whereby the reaction efficiencies were high and the water‐soluble derivatives exhibited excellent emulsifying efficiency as well as surfactant performance properties tested by washing power and antiredeposition efficiency. The results indicate also the high potential of both microwave and ultrasound energy sources to innovate and increase the efficiency of technological polysaccharide esterification processes.
Long alkyl chains (C 12 ) have been introduced onto glucuronoxylan and its sulfoethyl derivative via O-alkylation using 1-bromododecane in dimethylsulfoxide. The new amphiphilic xylan derivatives were characterized by chemical, elemental, and spectral analyses. They reduce the surface tension and exhibit remarkable emulsifying and protein foam-stabilizing properties. The results indicate that the development of new biopolymeric surfactants may be based on heteroxylans that are abundant in hardwoods and annual plants, and represent an unexploited renewable polysaccharide resource.
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