ALKYL POLYGLUCOSIDE C8-C14

EC number: 500-220-1

The technically important synthesis of alkyl polyglycosides from fatty alcohols and D‐glucose was investigated on a laboratory scale. A new simple method to quantify the rate of this complex reaction by measuring the formation of water is described. The influence of the concentration and the kind of the sulfonic acids used as catalysts on the reaction rate and the composition of the products was determined and correlated to the Taft‐constants σ*.

It was shown that the reaction rate observed for the different catalysts is mainly an effect of their acidity. Thus, neighbouring group effects of catalysts such as 10‐camphorsulfonic acid (bulky substituent) or sulfosuccinic acid (polar substituent) seem not to exist. Due to the heterogeneous character of the reaction the rate‐concentration plots gave saturation curves. Finally, the influence of the particle size of the crystalline glucose on the reaction rate and the composition of the product was investigated. The use of the finest‐grained glucose gave the best product with only a small amount of polymers and a high reaction rate.

ALKYL POLYGLUCOSIDE C8-C14 belongs to the alkyl polyglucosides family and can be applied as emulsifier 100% vegetable based for the Paints & Coatings and Lubricants industries Alkyl polyglycosides (APGs) are a class of non-ionic surfactants widely used in a variety of cosmetic, household, and industrial applications. Biodegradable and plant-derived from sugars, these surfactants are usually glucose derivatives, and fatty alcohols.

Decyl glucoside or decyl d-glucoside, also named decylbeta- d-glucopyranoside, belongs to the alkyl glucosides family and is obtained by condensation of the fatty alcohol decyl alcohol and a d-glucose polymer. This nonionic surfactant and cleansing agent has been widely used for several years, due to its foaming power and good tolerance in rinse-off products such as shampoos, hair dyes and colors, and soaps. 

Alkyl Polyglucoside surfactants (APG) are nononic surfactants, obtained from renewable, natural raw materials, such as vegetable oils and starch. Their first-rate environmental and skin compatibility profiles fit in well with consumer demands for wellness, green solutions, mildness to human skin, and safety for human health. Furthermore, they contribute to various performance benefits in personal and home care products as well as I&I applications.

Among all sugar‐based surfactants, alkyl polyglycosides (APG) are the most successful, with applications ranging from agricultural, chemicals, laundry detergents, and hard surface cleaners to personal care products. APGs show significant synergistic effects in conjunction with anionic surfactants. Alpha olefin sulphonate (AOS) is one such anionic surfactant that is fast gaining acceptability in detergents for its superior performance characteristics and enhanced biodegradability. The present article evaluates the detergency of APG surfactants with three different chain lengths C8/10, C12/14, and C12/18, against fatty soil, particulate soil, and oily soil. Further the synergistic effects with AOS on detergency performance of APG are studied.

The raw materials are typically starch and fat, and the final products are typically complex mixtures of compounds with different sugars comprising the hydrophilic end and alkyl groups of variable length comprising the hydrophobic end. When derived from glucose, they are known as alkyl polyglucosides.APG is used to enhance the formation of foams in detergents. It is also used in the personal care industry because it is biodegradable and safe for sensitive skin.

Alkyl glycosides are produced by combining a sugar such as glucose with a fatty alcohol in the presence of acid catalysts at elevated temperatures. Alkyl polyglucosides  (APG) is a relatively new generation of commercially available environmentally friendly, mild, low-toxic, less-irritating and readily biodegradable surfactants.Act as detergents, wetting agents, emulsifiers, solubilisers and foaming agents. In cosmetic, APG surfactant is used to formulate Shampoo, Face wash, Hand wash, Shower gel and many more cleansing products for skin and hair.

The raw material derived from glucose derivatives and fatty alcohols. Have minimal impact on the environment while efficiently maintaining the standard of cleaning and hygiene. Since the properties, Alkyl polyglucoside become very important as high-performance components for cosmetic preparations due to their excellent environmental and skin compatibility.

The carbon chain difference made Aklyl polyglucoside up to rough dozens of different products. For example, Decyl Glucoside formed by C8-14 and C12-C14 carbon chain alcohol. ​​Other alkyl glucoside ingredients that may use in cosmetics include Coco Glucoside(C8-10 and C12-C14 ratio different with decyl glucoside), Hexyl Glucoside (C6), Lauryl Glucoside (C12-C14), Iso Octyl Glucoside (C8), Capryl/Caprylyl Glucoside(C8-C10).These Products are free from 1-4 dioxane which is carcinogenic.

APG products showed low irritation to human skin and eyes. When formulated with anionic surfactants, APG products can reduce the irritation of the anionic surfactants.  The same reaction rate was observed for the one-step synthesis of APG from branched alcohols and from linear alcohols. Biodegradation studies showed that the primary biodegradability value of natural C8–10APG was slightly higher than for oxo-C10–11APG, and there was no significant difference between oxo-C12–13APG and C12–14APG. The primary biodegradability value of oxo-C14–15APG was lower than the four APG already named.

The goal of this study of the physicochemical properties of these APG of natural alcohol and oxo-alcohol was to evaluate their differences. Diversification of APG selection will help improve its physicochemical properties and expand its application fields. The results are that the wetting abilities of oxo-C10–11APG and oxo-C12–13APG are better than the natural alcohol C8–10APG and C12–14APG, whereas the foamabilities of oxo-C10–11APG and oxo-C12–13APG are worse than those for natural C8–10APG and C12–14APG. There are no real differences in surface tension and detergency between APG of natural alcohol and oxo-alcohol.

Use of alkyl polyglucosides (APGs) as a foaming agent during hot water weed control may influence the environmental fate of organic contaminants in soil. We studied the effects of the APG-based foaming agent NCC Spuma (C8-C10) on leaching of diuron, glyphosate, and polycyclic aromatic hydrocarbons (PAHs) in sand columns. We also examined how APG concentration affected the apparent water solubility and adsorption of the herbicides and of the PAHs acenaphthene, acenaphthylene and fluorene. Application of APGs at the recommended concentration of 0.3% did not significantly affect leaching of any of the compounds studied. However, at a concentration of 1.5%, leaching of both diuron and glyphosate was significantly increased.

The increased leaching corresponded to an increase in apparent water solubility of diuron and a decrease in glyphosate adsorption to the sand. However, APG addition did not significantly affect the mobility of PAHs even though their apparent water solubility was increased. These results suggest that application of APG-based foam during hot water weed control does not significantly affect the mobility of organic contaminants in soil if used according to recommendations. Moreover, they suggest that APGs could be useful for soil bioremediation purposes if higher concentrations are used.

Other Name: Caprylyl glucoside // Capryl glucoside

INCI Name: Decyl Glucoside

Molecular Formula: C16H32O6