Glyceryl ether sulfonates

Although essentially pure soap products continue lo dominate the cleansing-bar field, a few products contain synthetic surfactams in addition 10 soap to act as scum and curd dispersants. Synthetic surfactants used in this application include alkyl sulfates, alkyl glyceryl ether sulfonates, alkyl esters of sodium isothionale. and alkylamides of N-melhyl tauride. 

Miscellaneous—Including two other comparatively minor products—amine oxides and alkyl glyceryl ether sulfonates. 

The alkyl glyceryl ether sulfonates are prepared as follows ... 

Alkyl glyceryl ether sulfonates are found in some dishwashing liquids, shampoos, and detergent bars and are primarily used to enhance skin emolliency though some claims are made for "cleaning ability."... 

U.S. 5,084,212 (1992) Farris et al. (Procter Gamble) C8 alkyl glyceryl ether sulfonate foam enhancers Ultramild surfactant... 

N-acyl methyltaurates, N-acyl sarcosinates, acyl isethionates, IV-acyl polypeptide condensates, polyalkoxylated ether glycolates, monoglyceride sulfates, and fatty glyceryl ether sulfonates [1,23]. 

Polyalkoxylated ether glycolates (organic salts) yield a creamy lather and also provide some conditioning properties to the hair. Monoglyceryl sulfates exhibit properties similar to lauryl sulfates and do not offer any other additional advantages. Fatty glyceryl ether sulfonates exhibit mildness and superior flash foam and have the additional benefit of hydrolytic statriUty. ... 

Glyceryl ether sulfonates are surface-active anionic surfactants, which utilize a glyceryl backbone in the sulfonated group of the molecule. On the basis of patent literature, the first production of these ethers began with Alfred Kirstahler and Richard Hueter in the 1930s. Since this time, the process for the production of these surfactants has been significantly improved and optimized. 

The first step in the production of glyceryl ether sulfonates is the production of the intermediate glyceryl ether. There is a multitude of potential reactants that can be used as discussed in Section 8.2.1. Additionally, this reaction is an oligomer reaction, and hence, the intermediate is characterized by multiple chemical species, not just one. 

The chloro-glyceryl ethers described earlier can be converted into the final glyceryl ether sulfonate by a Streckerization reaction, that is, use of sodium sulfite to perform sulfonation. However, the resulting composition of the surfactant will have an increased amount of sodium chloride by-product, which is very difficult to remove from the product. Therefore, it is recommended that an additional reaction step be performed to dehalogenate the product into a glycidyl ether. 

Dichloro-glycidyl ether sulfite/ bisulfite Tri-glyceryl ether sulfonate... 

FIGURE 8.4 Chemistry for the production of glyceryl ether sulfonates from glycidyl ethers. 

It is important to note here that once again an inuniscible liquid system is encountered and good contact between the two phases is essential. A small amount of the alkyl glyceryl ether sulfonate product can be used as a seed to emulsify the two phases and provide more intimate contacting to increase the rate of reaction. ... 

Moisture content is another key variable to be controlled during the production of glyceryl ether sulfonates. The minimum amount of water in the system should be enough to keep the sodium sulfite, with its limited solubility, completely dissolved in the system. This is another advantage for using the modified Streckerization reaction since bisulfite is more soluble than sulfite, and as less sulfite is needed, the amount of water required is also reduced. The sulfonate product is also highly viscous with poor heat transfer. Therefore, an overall moisture concentration of 50% is recommended to lower the viscosity of the solution and allow for better temperature control. ... 

Results of Collagen Selling Test for Several Forms of Glyceryl Ether Sulfonates versus Other Synthetic Surfactants... 

Glyceryl ether sulfonate is a somewhat generic term for a sulfonated surfactant, which has a glycerin ester bond associated with it. The chemistry is well established in patent literature and a wide range of homologs can be produced. Depending on the application, the structure of these surfactants can be tailored to provide a multitude of desired benefits for a vast array of applications. 

Whyte, D.D. Alkyl glyceryl ether sulfonates, in Anionic Surfactants, Surfactant Science Series Volume 7, Linfield, W.M., Ed., Marcel Dekker, New York, Chapter 14, 1976. 

There appears to be a synergy between SMEs and sulfonated fatty acids, which allow for improved foam and feel of a soap bar while retaining ease of production. Existing equipment used to make pure soap bars may be able to make combo SME/sulfonated fatty acid/soap bars. Surfactants currently used in combo soap bars include alkylether sulfates, sodium cocoylisethionates, alkyl glyceryl ether sulfonates, and betaines. Incorporation of these surfactants generally requires special equipment and processing. 

Most bar soap is indeed soap. A few products consist of synthetic detergent. The products most often used are isethionate esters, alcohol sulfate, and alkyl glyceryl ether sulfonate. 

The alkyl glyceryl ether sulfonate class of surfactants, represented by the general formula... 

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