Soap‐based detergent formulations: XII. Alternate syntheses of surface active sulfobetaines

Abstract

Sulfopropylated amphoteric surfactants, previously reported in this journal, displayed excellent surface active properties and were good detergents in combination with soap. New synthetic routes were investigated for the preparation of such types of compounds to provide a more economical process and eliminate the hazards due to propanesultone, which was used in the previously reported synthetic procedure. A series of 2‐hydroxy‐3‐sulfopropyl amphoteric surfactants was prepared by reacting sodium 3‐chloro‐2‐hydroxy‐1‐propanesulfonate (the addition product of sodium bisulfite to epichlorophydrin) with various primary fatty amines as well as with fat derived N,N‐dimethylalkylamines. Quaternary sulfobetaines not possessing a hydroxyl group were obtained from tertiary amines by reaction with allyl chloride followed by bisulfite addition. The solubility behavior (Krafft points) of these compounds indicated that they were not identical with the sulfobetaines prepared with the aid of propanesultone. The secondary and quaternary ammonium compounds exhibited limited water solubility but were good lime soap dispersing agents. They displayed good detergency in combination with soap. The quaternary ammonium derivatives were particularly effective on cottonpolyester blend fabrics.

Soap‐based detergent formulations: XXIII. Synthesis of p‐sulfobenzyl ammonium inner salts and structural correlation with analogous amphoterics

“…The benzyl (I) sulfobetaines, reported in this paper, are illustrated below, as well as two-carbon (II), three-carbon (III), and four-carbon (IV) bridge sulfobetaines, studied previously by Parris et al (1,2). The benzyl (I) sulfobetaines, reported in this paper, are illustrated below, as well as two-carbon (II), three-carbon (III), and four-carbon (IV) bridge sulfobetaines, studied previously by Parris et al (1,2).…”

“…In the course of an ongoing study of soap-based detergents, amphoteric surfactants have been found to be effective lime soap dispersing agents (LSDA) and comparable to or better than a high-phosphate control in detergency performance when formulated with tallow soap and a silicate builder (1)(2)(3)o Specifically, amphoterics bearing a quaternary ammonium nitrogen and a terminal sulfonate group of the general structure, R~(CH3)2CnH2nSO3, where R is a long alkyl chain and n an integer from 2 to 4, have shown outstanding surface active properties, The introduction of an amido group to give amphoterics of the structure, RCONHCH2CH2CH2N(CH3)2CnH2nSOj, further enhances the lime soap dispersing ability and improves water solubility (lowers the Krafft point) (1,2).…”

Soap‐based detergent formulations: XVIII. Effect of structure variations on surface‐active properties of sulfur containing amphoteric surfactants

“…without a hydroxyl group in the bridge section of the molecule are included in Figure 1 from a previous publication (2) for comparison. It can be seen that the Krafft points of the sulfopropylated amphoterics with or without the hydroxyl substituent rise very steeply with increasing fatty alkyl chain length.…”

“…(3-Sulfopropyl)dimethyl(alkyl)ammonium inner salts previously prepared at this laboratory (1) possess good surface-active properties. The effect of the alkyl chain length on Krafft point was found to be much more pronounced for the quaternary (3-sulfopropyl) dimethyl(alkyl)arnmonium inner salt and (2-hydroxypropyl)dimethyl(alkyl)ammonium inner salt than for their secondary amino analogs (1,2). Poor water solubility, as indicated by Krafft point, tends to limit the utility of such surfactants.…”

Amphoteric Surface Active Agents with Heterocyclic Ring Based on Industrial Wastes

“…In general , grape seed oil is very similar to sunflower oil, it is a good all-round oil, high in essentional fatty acid linoleic , but very low in easily oxidized linolenic acid (5) ; it is also, low in saturates. It was interesting to prepare some biologically active simple heterocycles which constitute an important class of organic compounds with diverse biological activities (6)(7)(8)(9) . Numerous fatty S alcohols are now more available in their pure form and inexpensive enough to provide the chemical field with a wealth of reactions in which fatty alcohols are used as raw material in a variety of industrial products like pharmaceuticals (10)(11) , cosmetics, surfactants, paints,… etc.…”