Current changes in environmental legislation and customer demands set an urge for the development of more sustainable surfactants. Thus, the objective of this work was the development of novel environmentally friendly amino acid surfactants. Combining Diels–Alder cyclization of myrcene with maleic or citraconic anhydride followed by ring opening with amino acids enabled a synthesis route with a principal 100% atom economy. Variation of amino acids resulted in a large structural variety of anionic and amphoteric surfactants. Lysine gave access to either a mono-acylated product bearing a cationic side chain or a bi-acylated gemini surfactant. First, anhydride precursors were synthesized in yields of >90% in a Diels–Alder reaction under microwave radiation and subsequent amino acid coupling in aqueous environment gave fully bio-based surfactants in good yields and purity. Physicochemical characterization showed an enhanced decrease in surface tension upon addition of amino acids to the myrcene–anhydride backbone, resulting in a minimal value of 31 mN·m−1 for gemini–lysine. Foamabilitiy and foam stability were significantly increased at skin-friendly pH 5.5 by incorporation of amino acids. The carboxylic groups of surfactants with arginine were esterified with ethanol to access cationic compounds. Comparative analysis revealed moderate antimicrobial effects against yeast, Gram-positive bacteria, and Gram-negative bacteria.

In cleaning products, selecting the right surfactants for the specific soil or contamination is crucial. The hydrophilic-lipophilic deviation (HLD) concept serves as a useful formulation tool by describing the interactions between surfactants, oil and water. However, for mixtures of ionic and non-ionic surfactants, the HLD concept assumes ideal mixing behavior, which does not hold true. Therefore, interactions between different surfactants must be considered. This can be achieved by introducing the interaction term GEX/RT. Evaluating this interaction term using a set of equilibrated surfactant/oil/water (SOW) systems under various conditions is both time-consuming and resource intensive. This work aims to demonstrate the rapid determination of this interaction term using the dynamic phase salinity inversion (DSPI) method. We determined the phase behavior of a ternary surfactant system, consisting of sodium dioctyl sulfosuccinate, alkyl polyglucoside, and fatty alcohol ethoxylate, through both equilibrated systems and the DSPI method. Differences between the theoretical HLD calculations and actual experiments allowed us to access interaction terms. To validate GEX/RT obtained by DSPI, we employed net-average-curvature concept to model the interfacial tension under different conditions. Spinning drop measurements showed excellent agreement between theoretical and measured values, confirming the applicability of DSPI for determining interactions in this surfactant system. image

Starmerella bombicola is known to produce sub-terminally hydroxylated lactonic sophorolipids (SLs), while Candida kuoi synthesizes acidic open chain SLs with terminally hydroxylated fatty acids. Upon feeding glucose and fatty alcohols both strains form long-chain nonionic SLs. According to structure elucidation the SLs consist of a hydroxylated fatty acid esterified with fatty alcohol and linked via a glycoside bond to the diacetylated sophorose unit. Palmityl, stearyl, and oleyl alcohols lead to products with lipid chain lengths of C32 or C36. Oleyl alcohol is the preferred substrate leading to 45 g L-1 of the double unsaturated C36 SL with S. bombicola and 20 g L-1 with C. kuoi. Scale up from shake flask to 1.5 L fermentations is possible and 65 g L-1 long-chain SLs are obtained with S. bombicola within 7 days. Mixed feeding of oleic acid and a variety of fatty alcohols leads to new long-chain SLs. In the presence of oleic acid the yeasts do not oxidize the fatty alcohol and thus the production of biosurfactants with tailored chain length is possible. The long-chain SLs show good emulsification ability of water/paraffin oil mixtures at low energy input and reduced interfacial tension significantly. Practical Applications: Sophorolipids are produced by fermentation on industrial scale focusing on cleaning and detergent applications. Mainly lactonic or anionic open-chain forms are used today. The new long-chain SLs presented in this manuscript are accessible with existing production technology and can be produced with high titers from cost-efficient renewable raw materials. In contrast to the commercial products the long-chain SLs are more hydrophobic and exhibit a strong emulsification behavior. Therefore they have the potential to broaden the application range of SLs in future. They may be useful as novel emulsifiers for cosmetic creams and lotions, pharmaceutical ointments and food products or may find application in oil spill remediation.

Abstract Starmerella bombicola and Candida kuoi are known to secrete structurally divergent sophorolipid type glycolipids (SLs) under nitrogen limitation. In the present work SLs were produced in titers of 3.9–78.6 g L−1 with the two yeast strains utilizing stearic, oleic and linoleic acid as substrates. HPLC-ELSD combined with HPLC-MS and NMR spectroscopy was used for qualitative and quantitative analysis of the SL mixtures. While S. bombicola almost exclusively produced lactonic diacetylated SLs with a preference for subterminal fatty acid hydroxylation, C. kuoi synthesized diacetylated, terminally hydroxylated open chain SLs with up to 25% of dimeric and trimeric products. Surface tension measurements showed a higher surface and interface activity of the lactonic products from S. bombicola in comparison to open chain C. kuoi based SLs. The lowest CMC of 5.4 mg L−1 and minimum surface tension at the CMC of 35.9 mN m−1 were obtained for the stearic acid based lactones. Similar tendencies were observed in interfacial tension analysis with 3.6 mN m−1 for oleic acid based lactonic SLs at the interface water/paraffin oil in comparison to 9.4 mN m−1 for the corresponding open-chain SL. The acidic C. kuoi SL mixtures directly exhibited foaming properties whereas the S. bombicola SLs needed alkaline deacetylation and ring opening to display foaming comparable to that of the structurally related alkyl polyglycosides.

Le menagement des couleurs par des produits lessiviels utilises pour laver des textiles de couleur doit etre ameliore. Ce but est atteint essentiellement du fait qu'on utilise des derives de triazine comprenant au moins une substitution d'aniline sur le cycle de triazine.

Die Anmeldung beschreibt ein flussiges Wasch- oder Reinigungsmittel, umfassend a) einen alkoxylierten Oxo-Alkohol mit 7 oder 8 Alkoxyeinheiten und b) ein schmutzablosevermogendes Polymer. Das flussige Wasch- oder Reinigungsmittel weist eine erhohte Reinigungsleistung, insbesondere an Fetthaltigen Anschmutzungen, und eine verbesserte Vergrauungsinhibierung auf.

L'invention concerne un agent detergent ou de nettoyage liquide renfermant un polysaccharide inhibant le grisage. L'invention concerne egalement l'utilisation de l'agent detergent ou de nettoyage liquide, ainsi qu'un procede pour sa production.