Preparation and properties of new lactose‐based surfactants

Abstract

A new group of nonionic saccharide-based surfactants, N-alkanoyl-N-methyllactitolamines (alkanoyl: decanoyl, lauroyl, myristoyl, palmitoyl, stearoyl), were synthesized and characterized. Surface properties such as critical micelle concentration, standard free energy of adsorption, standard free energy of micellization, surface tension reduction efficiency, effectiveness of surface tension reduction, surface excess concentration, and surface area demand per molecule as well as foaming properties (i.e., foam volume and foam stability), contact angle, antimicrobial activity, and biodegradability were determined. The selected performance properties were evaluated in relation to commercially available alkyl polyglucosides (Glukopon 600 EC(HH)-a Henkel product), and oligooxyethylenated decyl (C 10 E 4 ) and dodecyl (C 12 E 5 ) alcohols. The foaming-stabilizing effect and contact angle suggest that the lactose-derived surfactants that were studied share some common properties with alkyl polyglucosides that are different from those with an oligooxyethylene grouping. All tested N-alkanoyl-N-methyllactitolamines were practically nontoxic to bacteria and yeasts. These compounds are readily biodegradable in the Closed Bottle test inoculated with activated sludge. N-Alkanoyl-N-methyllactitolamines with lower chain lengths (C 10 -C 14 ) biodegraded at a slightly faster rate. Biological properties showed that this class of compounds fulfills all requirements needed for environmental acceptance.Paper no. S1211 in JSD 4, 155-161 (April 2001).KEY WORDS: N-Alkanoyl-N-methyllactitolamines, antimicrobial activity, biodegradability, contact angle, foaming ability, nonionic lactose-derived surfactants, surface activity.Nonionic surfactants bearing a carbohydrate moiety as the hydrophilic part (so-called saccharide or sugar surfactants) have recently received increasing interest because they have improved surface and performance properties, reduced environmental impact, and they have potential pharmaceutical and biomedical applications (1-4). Because of these valuable features, many research groups have directed their studies to various aspects of synthetic methodologies and properties of a wide range of saccharide surfactants that vary in their molecular architecture, such as single-chain, single-head entities (5-12), di-chained (13,14) and dicephalic compounds (15,16) as well as bolaamphiphiles and gemini structures (17,18). Accordingly, all of these saccharide-derived materials exhibit similar general trends in surface-active behavior as reported for polyoxyethylene-based nonionics. However, the absence of a cloud point for aqueous solutions of saccharidebased nonionics indicates that the carbohydrate segments do not undergo dehydration with increasing temperature and that their interactions with water molecules are more favorable than the corresponding interactions between water molecules and polyoxyethylene segments. As a continuation of our studies (8,12,15,16) related to nonionic surfactants comprising various carbohydrate hydrop...

Review on chemically bonded geminis with cationic heads: second-generation interfactants

“…4 Zn(II) mediated cleavage of a phosphate diester in the stern layer of cationic gemini 16-2-16 [43] stronger hydrophilicity as compared with surfactants with oligo ethylene oxide head groups, and the hydrophobic part could consist of one, two, or even more chains such as hydrocarbon chains of fatty acids, long-chain fatty amines, or alcohols [44][45][46][47][48][49][50][51][52][53][54]. Novel green geminis derived from glucose and glucitol are able to show thermotropic behavior [55].…”

Adsorption and micellization behavior of novel gluconamide-type gemini surfactants

“…With the expectation for the biodegradability, non-toxicity and biocompatibility, the absence of the cloud point enables us to use the sugar-based surfactants in a wide variety of applications such as detergents, dish-washing agents and personal care products [9,10]. During the last decade gemini surfactants containing sugar moieties in their headgroups have been synthesized and the aqueous solution properties have been studied: one typical series of this type of gemini surfactants is made from monosaccharides (or their derivatives) [11][12][13][14][15][16][17][18][19][20] and the other is made from disaccharides (or their derivatives) [13,14,21]. In addition, sugar-based gemini surfactants with a disaccharide spacer have been synthesized by Menger and Mbadugha [22].…”

Surface and micellar properties of new nonionic gemini aldonamide-type surfactants

“…In our previous papers, we described the synthesis and surface properties of a variety of saccharide-derived surfactants, namely N -alkylaldonamides [13,14] and N -alkanoyl-N -methyllactitolamines [15], having a single-chain, singlehead structure, and so-called dicephalic compounds, comprising one hydrophobic tail and two aldonamide entities linked by a connector to a nitrogen bridge [16]. As a continuation of our studies upon environmentally acceptable surfactants, we present here a new family of nonionic dimerics, N,N -bisalkyl-N,N -bis[(3-aldonylamide)propyl]ethylenediamines [17], of the general formula shown (together with abbreviations) in Scheme 1.…”