Use of monoester glycolipids in laundry detergents

Abstract

The present invention relates to the use of monoester glycolipids or mixtures of monoester glycolipids in laundry detergent compositions. The monoester glycolipids or mixtures of monoester glycolipids include a carbohydrate fraction selected from the group consisting of maltose, cellobiose, trehalose, isomaltulose, lactulose, isomaltose and mixtures thereof.

Description

Technical Field

[0001] This invention relates to laundry detergents. Background Art

[0002] Laundry detergents are compositions used to remove unwanted substances from textiles / clothes during the washing process. The most important class of compounds in laundry detergents are surfactants, also known as surface-active substances. Surfactants consist of both hydrophilic and hydrophobic portions, which makes them suitable for diffusion in water and adsorption at the interface between water and unwanted substances on the textiles. Simply put, surfactant molecules align and surround the unwanted substance, releasing it from the textiles to form micelles, within which the unwanted substance resides.

[0003] Properties such as wetting ability, foaming ability, and dispersing ability can be tuned by altering the hydrophilic and / or hydrophobic portions. Therefore, surfactants differ in their ability to remove specific types of unwanted substances, their effectiveness on different types of textiles, and their response to water hardness.

[0004] The surfactants currently in use have shown great effectiveness. However, consumer demand for new, gentler, and "more environmentally friendly" laundry detergents means that this area needs to be re-examined. Summary of the Invention

[0005] Therefore, the purpose of this invention is to provide a more environmentally friendly alternative to currently used laundry detergents.

[0006] The inventors of this invention have discovered the use of a new subtype of nonionic surfactant—monoester glycolipid—which is a more environmentally friendly alternative to traditional nonionic surfactants in laundry detergents.

[0007] The inventors of this invention have also discovered a process for producing monoester glycolipids from renewable resources, such as enzymatically hydrolyzed starch (e.g., maltose) and used edible oils (e.g., sunflower oil, rapeseed oil, corn oil, and olive oil). Furthermore, these monoester glycolipids are biodegradable. Some byproducts (monoglycerides and diglycerides) can even be separated as valuable food ingredients or food additives.

[0008] Therefore, the first aspect relates to the use of monoester glycolipids or mixtures of monoester glycolipids in laundry detergent compositions.

[0009] The second aspect relates to a laundry detergent composition comprising monoester glycolipids or mixtures of monoester glycolipids.

[0010] The third aspect relates to a method for cleaning textiles and / or textile articles, comprising the following steps:

[0011] - Provides a laundry detergent composition comprising monoester glycolipids or a mixture of monoester glycolipids, wherein the concentration is such that it effectively cleans fabrics / textile articles under predetermined washing conditions;

[0012] - At one or more points during the washing process, one or more textiles and / or textile articles are brought into contact with the laundry detergent composition; and

[0013] - Allow the textiles and / or textile articles to dry, or to be mechanically tumble dried.

[0014] The invention will now be described in more detail. Detailed Implementation

[0015] Glycolipids are amphoteric, anionic, cationic, or nonionic molecules comprising a hydrophilic carbohydrate moiety and one or more fatty acids as lipophilic moieties. Monoester glycolipids have a single fatty acid as the lipophilic moiety. The inventors of this invention have also found that monoester glycolipids exhibit comparable, and sometimes better, performance compared to some conventional nonionic surfactants produced from petrochemicals and palm oil (see the Experimental Section for selection of results).

[0016] The first aspect relates to the use of monoester glycolipids or mixtures of monoester glycolipids in laundry detergent compositions.

[0017] The second aspect relates to a laundry detergent composition comprising monoester glycolipids or mixtures of monoester glycolipids.

[0018] The inventors of this invention have discovered a process for producing monoester glycolipids from renewable resources.

[0019] The laundry detergent composition of the present invention can be in any of a variety of forms. It can be in the form of a dilutable laundry detergent, a surfactant-structured liquid, granules, spray-dried or dry-mixed powder, tablets, paste, molded solid, or any other laundry detergent form known to those skilled in the art.

[0020] For the purposes of this disclosure, a “dilutable laundry detergent” composition is defined as a product intended to produce a liquid suitable for cleaning textiles by dilution with water at a ratio of more than 100:1. Water-soluble sheets or pouches, such as those described in U.S. Patent Application No. 20020187909, are also contemplated as potential forms of the invention. These products may be sold under various names and used for a variety of purposes.

[0021] How to use

[0022] The following describes in detail a method for cleaning textiles and / or textile articles, including the following steps in any order:

[0023] i. Providing a laundry detergent composition comprising monoester glycolipids or a mixture of monoester glycolipids, wherein the concentration is such that it effectively cleans fabrics and / or textile articles under predetermined washing conditions;

[0024] ii. At one or more points during the washing process, contact one or more textiles and / or textile articles with the laundry detergent composition; and

[0025] iii. Allow the textiles and / or textile articles to dry or to be mechanically tumble dried.

[0026] The dosage of laundry detergent compositions typically ranges from about 10g to about 300g of total product per 3kg of textiles, depending on the specific implementation method chosen and other factors that influence product usage behavior, such as consumer preferences.

[0027] Consumers using this invention may, according to specific instructions, contact textile products such as clothing with the composition of this invention, with the aim of simultaneously cleaning and softening the textile products. This method is recommended when the composition is in the form of a softening detergent and needs to be added at the beginning of a washing cycle.

[0028] In addition to the aforementioned monoester glycolipids, formulators also include one or more optional ingredients in laundry detergent compositions. While the presence of these elements is not necessarily required to carry out this invention, the use of such substances often greatly helps to make the formulation of laundry detergent compositions more acceptable to consumers.

[0029] Examples of optional components include, but are not limited to: anionic surfactants, nonionic surfactants, amphoteric and zwitterionic surfactants, cationic surfactants, solubilizers, optical brighteners, photobleaching agents, fiber lubricants, reducing agents, enzymes, enzyme stabilizers, powder finishing agents, defoamers, detergent builders, bleaching agents, bleaching catalysts, dirt release agents, anti-redeposition agents, dye transfer inhibitors, buffers, colorants, fragrances, fragrance precursors, rheology modifiers, anti-ashing polymers, preservatives, insect repellents, stain repellents, waterproofing agents, suspending agents, sensory modifiers, structural agents, disinfectants, solvents, fabric finishing agents, color-fixing agents, anti-wrinkle agents, fabric conditioning agents, and deodorants.

[0030] In one or more embodiments, the laundry detergent composition further comprises:

[0031] - One or more enzymes.

[0032] The laundry detergent composition may further include one or more enzymes that provide cleaning performance and / or fabric care benefits. The enzymes may include cellulase, hemicellulase, peroxidase, protease, glucosylamylase, amylase, lipase, keratinase, pectinase, xylanase, mannanase, pectic acid lyase, reductase, oxidase, phenol oxidase, lipoxygenase, ligninase, pullulanase, tanninase, pentosanase, maltase, β-glucanase, arabinosidase, or mixtures thereof.

[0033] Preferred combinations are laundry detergent compositions having a mixture of conventionally applicable enzymes, such as proteases, amylases, lipases, keratins and / or cellulases, combined with a lipolytic enzyme variant D96L at a level of 50 LU to 8500 LU per liter in the washing solution.

[0034] The preferred lipases are selected from the *Thermomyces lanuginosa* lipase family. The *Thermomyces lanuginosa* lipase family refers to a group of lipases primarily derived from the thermophilic fungus *Thermomyces lanuginosa*. These enzymes are known for their ability to break down lipids (fat) and possess several unique properties, such as thermal stability and substrate specificity.

[0035] Suitable cellulases include both bacterial and fungal cellulases. Preferably, their optimal pH is between 5 and 9.5. Suitable cellulases are disclosed in U.S. Patent No. 4,435,307, which discloses a fungal cellulase produced by *Humicola insolens*. Suitable cellulases are also disclosed in GB-A-2075028, GB-A-2095275, and DE-OS-2247832.

[0036] Examples of such cellulases are those produced by strains of specific *Humicola grisea* var. *thermoidea*, particularly strain DSM 1800. Other suitable cellulases are those derived from specific *Humicola grisea* with a molecular weight of approximately 50,000, an isoelectric point of 5.5, and containing at least 415 amino acid units. Particularly suitable cellulases are those with color-protecting properties. Examples of such cellulases are those described in European Patent Application No. 91202879.2. Preferred commercially available cellulases include those produced by Novozymes A / S under the trade name... The cellulase sold is produced by IFF under the trade name... Cellulase sold, and by AB Enzymes under the trade name Cellulase for sale.

[0037] Peroxidases are typically used in conjunction with oxygen sources such as percarbonates, perborates, persulfates, and hydrogen peroxide. They are used for "solution bleaching," which prevents dyes or pigments removed from the substrate during a cleaning run from transferring to other substrates in the cleaning solution. Peroxidases are enzymes known in the art, including, for example, horseradish peroxidase, ligninase, and haloperoxidases such as chloride peroxidase and bromoperoxidase. Detergent compositions containing peroxidases are disclosed, for example, in PCT International Patent Application WO 89 / 099813 and European Patent Application No. 91202882.6.

[0038] Cellulase and / or peroxidase are typically incorporated into the laundry detergent composition at a level of 0.0001% to 2% of the active enzymes by weight of the laundry detergent composition.

[0039] Preferred commercially available proteases include those produced by Novozymes A / S under the trade name... and Protease sold by Gist-Brocades under the brand name and Proteases sold; proteases sold by Genencor International; proteases sold by Solvay Enzymes under the trade name and Proteases sold by IFF under the trade name and Proteases sold; and proteases produced by AB Enzymes under the trade name The protease sold by ROC 250LCO. Other proteases described in U.S. Patent No. 5,679,630 may also be included in this detergent composition.

[0040] The protease may be incorporated into the detergent composition at a level of about 0.0001% to about 2% of the active enzyme by weight of the composition.

[0041] The preferred protease, referred to herein as "protease D," is a carbonyl hydrolase variant with an amino acid sequence not found in nature. This carbonyl hydrolase variant is derived from a precursor carbonyl hydrolase, obtained by combining the amino acid sequence of the carbonyl hydrolase with that of Bacillus amyloliquefaciens. The subtilisin is obtained by replacing an amino acid residue at position +76, which is preferably also combined with one or more amino acid residue positions selected from the group consisting of: +99, +101, +103, +104, +107, +123, +27, +105, +109, +126, +128, +135, +156, +166, +195, +197, +204, +206, +210, +216, +217, +218, +222, +260, +265 and / or +274, as described in U.S. Patent No. 5,679,630, the entire teachings of which are incorporated herein by reference.

[0042] Highly preferred enzymes that may be included in detergent compositions include lipases. Studies have found that the use of lipases synergistically enhances the cleaning effect on oily stains. Lipases are enzymes that catalyze the hydrolysis of fats and oils into fatty acids and glycerol, monoglycerides, and / or diglycerides. Lipases suitable for use herein include those derived from animals, plants, fungi, and microorganisms. Suitable lipases may be found in the cambium, bark, plant roots, and in the seeds of fruits, oil palm, lettuce, rice, bran, barley and malt, wheat, oats and oat flour, cottonseed kernels, corn, millet, coconut, walnuts, Fusarium, hemp, and cucurbits. In addition to naturally occurring lipases, chemically modified or protein-engineered mutants may also be used.

[0043] Suitable lipases include those derived from humic fungi (also known as thermophilic fungi), such as those from *H. lanuginosus* (or *T. lanuginosus*), as described in EP 258 068 and EP 305 216; or lipases from *H. insolens* (see, for example, PCT International Application WO 96 / 13580); Pseudomonas lipases, such as those from *P. alcaligenes* or *P. pseudoalcaligenes* (see, for example, EP 218272); and *P. cepacia* (see, for example, EP 218272). 331376), *Pseudomonas stutzeri* (see, for example, UK Patent No. 1,372,034), *Pseudomonas fluorescens*, *Pseudomonas* strain SD 705 (see, for example, PCT International Applications WO 95 / 06720 and WO 96 / 27002), or *Pseudomonas wisconsinensis* (see, for example, PCT International Application WO 96 / 12012); or Bacillus lipases, such as those derived from *Bacillus subtilis*, *Bacillus stearothermophilus*, or *Bacillus pumilus* (see, for example, PCT International Application WO91 / 16422).

[0044] Lipase variants may be used, such as those described in U.S. Patents 8,187,854, 7,396,657, and 6,156,552, the entire contents of which are incorporated herein by reference. Other lipase variants are also described in PCT International Applications WO 92 / 05249, WO 94 / 01541, WO 95 / 35381, WO 96 / 00292, WO 95 / 30744, WO 94 / 25578, WO 95 / 14783, WO 95 / 22615, WO 97 / 04079, and WO 97 / 07202, as well as EP 0 407 225 and EP0260105.

[0045] Suitable lipases include those marketed under the trade names Lipex™, Lipolex™, Lipoclean™, Lipolase™, Lipolase Ultra™, Lipopan™, Lipopan Xtra™, Lypozyme™, Palatase™, Resinase™, Novozym™ 435, and Lipoprime™ (all from Novozymes). Other suitable lipases available are Lipase P Amano™ (Amano Pharmaceutical). Further suitable lipases are those such as M1Lipase™ and Lipomax™ (DSM), Lumafast™ (Danisco), and Preferenz L (IFF). Preferred lipases include the D96L lipase variant of a natural lipase derived from *Humicola lanuginosa*, as described in U.S. Patent No. 6,017,871. Preferably, *Humicola lanuginosa* strain DSM 4106 is used.

[0046] Lipase can be used at any suitable level. Typically, the amount of lipase present in a laundry detergent composition is 10 to 20,000 LU / g, or even 100 to 10,000 LU / g. The LU unit for lipase activity is defined in WO99 / 42566. In the washing solution, the dosage of lipase is typically 0.01 to 5 mg / L of active lipase protein, more typically 0.1 to 2 mg / L. The amount of lipase in the detergent, by weight percentage, can be 0.00001 to 2 wt.%, typically 0.0001 to 1 wt.%, or even 0.001 to 0.5 wt.%.

[0047] Lipases can be incorporated into detergents in any convenient form, such as dust-free particles, stabilized liquids, or protected (e.g., coated) particles.

[0048] For further examples of suitable lipases used herein, see U.S. Patent Nos. 5,069,810; 5,093,256; 5,153,135; 5,614,484; 5,763,383; 6,177,012; 6,897,033; 7,790,666; 8,691,743 and 8,859,480, and U.S. Patent Application Publication No. 2011 / 0212877, the teachings of which are incorporated herein by reference.

[0049] Amylases (α and / or β) may be included for removing carbohydrate-based stains. Suitable amylases are... (Novozymes) (Novozymes) Novozymes, Stainzymes (Novozymes) (Novozymes) (Novozymes) (IFF) and (IFF).

[0050] The enzymes mentioned above can be derived from any suitable source, such as plant, animal, bacterial, fungal, and / or yeast sources. See U.S. Patent No. 5,929,022, the teachings of which are incorporated herein by reference, and much of the above discussion is derived from that patent. Preferred compositions optionally comprise enzymes or combinations of single enzymes, each typically ranging from 0.0001% to 2%.

[0051] Other enzymes and materials used with the enzyme are described in PCT International Patent Application No. WO99 / 05242, which is incorporated herein by reference.

[0052] Builders are typically added to fabric cleaning compositions to complex and remove alkaline earth metal ions, which can bind to anionic surfactants and be removed from the washing solution, thus interfering with the cleaning performance of the detergent. Preferred compositions of the present invention, particularly when used as detergent / softener combinations, contain builders.

[0053] Soluble detergent builders, such as alkali metal carbonates and alkali metal citrates, are particularly preferred, especially for the liquid embodiments of the present invention. However, other detergent builders may also be used, as described in further detail below. Typically, a mixture of several detergent builders selected from those described below and other detergent builders known to those skilled in the art will be used.

[0054] Alkali metal carbonates and alkaline earth metal carbonates, such as those detailed in German patent application 2,321,001 (published November 15, 1973), are suitable for use as detergent builders in the compositions of the present invention. They can be supplied and used in anhydrous form or in form including bound water. Sodium carbonate, or soda ash, is particularly useful, as it is readily available on the commercial market and has excellent environmental properties.

[0055] The sodium carbonate used in this invention can be natural or synthetic, and can be used in heavy or light form depending on the formulation requirements. Natural soda ash is typically mined as trona and further refined to a specific purity required for product use. Synthetic soda ash, on the other hand, is typically produced via the Solvay process or as a byproduct of other manufacturing processes such as caprolactam synthesis. Sometimes, including a small amount of calcium carbonate in the detergent formulation is more useful, as it acts as a seed crystal to promote crystallization, thereby improving the detergent's effectiveness.

[0056] Organic detergent builders can also be used as non-phosphate builders in this invention. Examples of organic builders include alkali metal citrates, succinates, malonates, fatty acid sulfonates, fatty acid carboxylates, nitrilotriacetates, oxodisuccinates, alkyldisuccinates and alkenyldisuccinates, oxodiacetates, carboxymethoxysuccinates, ethylenediaminetetraacetate, tartaric acid monosuccinate, tartaric acid disuccinate, tartaric acid monoacetate, tartaric acid diacetate, oxidized starch, oxidized heteropolysaccharides, polyhydroxysulfonates, polycarboxylates (such as polyacrylates, polymaleates, polyacetates, polyhydroxyacrylates, polyacrylate / polymaleate and polyacrylate / polymethacrylate copolymers), acrylate / maleate / vinyl alcohol terpolymers, amino polycarboxylates and polyacetal carboxylates, and polyaspartate salts and mixtures thereof. Such carboxylates are described in U.S. Patent Nos. 4,144,226, 4,146,495, and 4,686,062. Alkali metal citrates, hyponitrotriacetic acids, oxodisuccinates, acrylate / maleate copolymers, and acrylate / maleate / vinyl alcohol terpolymers are particularly preferred non-phosphate builders.

[0057] The compositions of the present invention utilize water-soluble phosphate builders, which typically contain 1% to 90% of the builder by weight of the composition. Specific examples of water-soluble phosphate builders are alkali metal tripolyphosphates, sodium pyrophosphate, potassium pyrophosphate and ammonium pyrophosphate, sodium orthophosphate and potassium orthophosphate, sodium polymetaphosphate (wherein the degree of polymerization ranges from about 6 to 21), and phytates. Sodium tripolyphosphate or potassium tripolyphosphate is most preferred.

[0058] However, phosphates are generally difficult to formulate, particularly into liquid products, and have been identified as a potential contributor to eutrophication of lakes and other waterways. Therefore, the preferred compositions of this invention comprise less than about 10% phosphate by weight, more preferably less than about 5% by weight. The most preferred compositions of this invention are formulated as substantially phosphate-free detergent builders.

[0059] Zeolite can also be used as a detergent additive in this invention. A wide variety of zeolites suitable for incorporation into the products disclosed herein are available for formulators, including the common 4A zeolite. Furthermore, MAP series zeolites can also be used for incorporation, such as the zeolite taught in European patent application EP 384,070B, which is commercially sold by, for example, Ineos Silicas (UK) under the trade name Doucil A24. MAP is defined as an alkali metal aluminosilicate of p-type zeolite having a silica-to-alumina ratio not exceeding 1.33, preferably in the range of 0.90 to 1.33, and more preferably in the range of 0.90 to 1.20.

[0060] Particularly preferred are MAP-type zeolites with a silica-to-alumina ratio of no more than 1.07, more preferably about 1.00. The particle size of the zeolite is not a critical factor. Any type A or MAP-type zeolite of suitable particle size can be used. However, since zeolite is an insoluble substance, it is advantageous to minimize its content in the compositions of the present invention. Therefore, preferred formulations contain less than about 10% zeolite detergent additive, and particularly preferred compositions include less than about 5% zeolite.

[0061] When enzymes, especially proteases, are used in liquid detergent formulations, it is usually necessary to include an appropriate amount of enzyme stabilizer to temporarily inactivate them before washing. Examples of suitable enzyme stabilizers are well known to those skilled in the art, including borates and polyols such as propylene glycol. Borates are particularly well-suited for use as enzyme stabilizers because, in addition to this function, they can buffer the pH of detergent products over a wide range, thus providing excellent flexibility.

[0062] If a borate-based enzyme stabilization system is chosen, and one or more cationic polymers that at least partially contain carbohydrate moieties are used simultaneously, stability problems may arise without the use of a suitable co-stabilizer. This is believed to be due to the natural affinity of borates for hydroxyl groups, which may form insoluble borate-polymer complexes that precipitate from solution over time or at low temperatures. This can usually be prevented by incorporating a co-stabilizer (typically a glycol or polyol, sugar, or other molecule with a large number of hydroxyl groups) into the formulation. Sorbitol is particularly preferred as a co-stabilizer, used at a level of at least about 0.8 times the borate level in the system, more preferably 1.0 times the borate level, and most preferably more than 1.43 times the borate level. Sorbitol is effective, inexpensive, biodegradable, and readily available in the market. Similar materials, including sugars such as glucose and sucrose, and other polyols such as propylene glycol, glycerol, mannitol, maltitol, and xylitol, should also be considered within the scope of this invention.

[0063] To enhance the conditioning, softening, wrinkle-resistant, and protective effects of the compositions of the present invention, it is generally desirable to include one or more fiber lubricants in the formulation. Such components are well known to those skilled in the art and are designed to reduce the coefficient of friction between fibers and yarns in the treated article during and after the washing process. This effect, in turn, can improve the consumer's perception of softness, minimize wrinkle formation, and prevent damage to textiles during washing. For the purposes of this disclosure, "fiber lubricant" should be understood as a non-cationic material designed to lubricate fibers with the aim of reducing friction between fibers or yarns in articles including textiles, thereby providing one or more wrinkle-resistant, fabric conditioning, or protective effects.

[0064] Examples of suitable fiber lubricants include oily sugar derivatives, functionalized animal and plant-derived oils, silicone oils, mineral oils, natural waxes, and synthetic waxes.

[0065] Oily sugar derivatives suitable for use in this invention are taught in WO 98 / 16538, which is incorporated herein by reference. Such substances are particularly preferred as fiber lubricants due to their readily available and environmentally friendly properties. When used in the compositions of this invention, these substances are typically present in the finished composition at levels between about 1% and about 10%. Another class of acceptable ingredients includes hydrophilically modified vegetable and animal oils, as well as synthetic triglycerides. Suitable and preferred hydrophilically modified vegetable, animal, and synthetic triglyceride oils and waxes have been identified as effective fiber lubricants. Such suitable plant-derived triglyceride substances include hydrophilically modified triglyceride oils (e.g., sulfated, sulfonated, carboxylated, alkoxylated, esterified, glycosylated, and amide-derived oils), tall oils, and their derivatives. Suitable animal-derived triglyceride substances include hydrophilically modified fish oil, tallow, lard, and lanolin waxes. A particularly preferred functional oil is sulfated castor oil, for example, which is commercially sold under the trade name Freedom SCO-75 from Noveon (Cleveland, Ohio).

[0066] Different degrees of derivatization can be used as long as the degree of derivatization is sufficient to make the oil or wax derivative soluble or dispersible in the solvent used, thereby providing fiber lubrication during the washing of fabrics with detergents containing the oil or wax derivative.

[0067] If the present invention includes synthetically derived functionalized oils, the oil is preferably a silicone oil. More preferably, it is a siloxane polyether or an amino-amino functionalized siloxane.

[0068] In many liquid and powder detergent compositions, cosolvents are typically added to adjust product viscosity, prevent phase separation in liquids, and facilitate powder dissolution. Two classes of cosolvents are commonly used in detergent formulations, and both are applicable to this invention. The first class consists of short-chain functionalized amphiphilic molecules. Examples of short-chain amphiphilic molecules include alkali metal salts of xylenesulfonic acid, isopropylbenzenesulfonic acid, and octylsulfonic acid. Additionally, organic solvents, as well as mono- and polyols with molecular weights below about 500, such as ethanol, isopropanol, acetone, propylene glycol, and glycerol, can also be used as cosolvents.

[0069] To prevent re-staining of fabrics during and after washing, one or more soil-releasing agents may be added to the products of this invention. Those skilled in the art are familiar with a variety of different types of soil-releasing agents, and the specific choice depends on the formulation used and the desired effect. In the context of this invention, useful soil-releasing agents are generally anti-redeposition auxiliaries or stain-resistant finishing agents. Examples of anti-redeposition agents include soil-releasing polymers, such as those described in WO99 / 03963, which is incorporated herein by reference.

[0070] Preferably, the carbohydrate portion of the monoester glycolipid is a disaccharide. Preferred disaccharides include, for example, maltose, sucrose, lactose, cellobiose, trehalose, and isomaltose. Preferably, the disaccharide is derived from a polysaccharide, such as starch, for example, through enzymatic cleavage. The inventors of this invention have discovered that, possibly due to steric hindrance, when the carbohydrate is glucose, only the C6-ol reacts with the fatty acid; while when the carbohydrate is maltose, the C6-ol or C6'-ol reacts with the fatty acid. In one or more embodiments, the monoester glycolipid or a mixture of monoester glycolipids includes a carbohydrate portion, said carbohydrate portion being maltose.

[0071] In one or more embodiments, the carbohydrate portion of the monoester glycolipid is selected from the group consisting of maltose, cellobiose, trehalose, isomaltulose, lactulose, isomaltose, and mixtures thereof.

[0072] In one or more embodiments, the carbohydrate portion of the monoester glycolipid is selected from the group consisting of maltose, cellobiose, trehalose, and mixtures thereof.

[0073] In one or more embodiments, monoester glycolipids or mixtures of monoester glycolipids comprise a disaccharide carbohydrate portion derived from a polysaccharide such as starch, for example by enzymatic cleavage.

[0074] In one or more embodiments, the monoester glycolipid or mixture of monoester glycolipids comprises a carbohydrate portion selected from the group consisting of maltose, cellobiose, trehalose, isomaltulose, lactulose, and isomaltose.

[0075] The performance of a surfactant depends on the balance between its hydrophilic head group and hydrophobic tail group. For monoester glycolipids, this corresponds to the hydrophilicity of the carbohydrate moiety and the hydrophobicity of the hydrocarbon moiety. For disaccharides, their solubility in water (and therefore their hydrophilicity) can differ by up to an order of magnitude (as shown in the table below). This makes it difficult to predict whether surfactants made from these different disaccharides will exhibit similar properties and whether they are suitable for use in laundry detergent formulations.

[0076] disaccharide Solubility in water (g / mL) sucrose 2.1 maltose 1.1 lactose 0.19 Trehalose 0.69 Cellobiose 0.12 Isomaltose 0.5 Isomaltulose 0.29 lactulose 0.76

[0077] In one or more embodiments, the lipid portion of the monoester glycolipid is derived from diglycerides and / or triglycerides selected from the following sources: sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, tallow, lard, rice bran oil, coconut oil, flaxseed oil, palm oil, shea butter, shea butter oil, mango oil, Kalahari seed oil, almond oil, poppy seed oil, plum kernel oil, grape seed oil, apricot kernel oil, and mixtures thereof. The most common fatty acids present in many of these oils are oleic acid, linoleic acid, stearic acid, and palmitic acid (as clearly shown in the table below), therefore their lipid portion is primarily one of these four fatty acids.

[0078]

[0079] As used herein, the term "glyceride" (also known as acylglycerol) refers to monoglycerides, diglycerides, triglycerides, or combinations thereof. These are esters formed from glycerol and fatty acids. Glycerides in oils may include a variety of saturated and unsaturated fatty acids. As used herein, the term "triglyceride" refers to an ester formed from glycerol and three fatty acids. The triglycerides of this disclosure may be saturated or unsaturated. Similarly, the term "diglyceride" refers to an ester formed from glycerol and two fatty acids, while the term "monoglyceride" refers to an ester formed from glycerol and one fatty acid.

[0080] Preferably, the triglyceride source is selected from sources consisting of: sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, beef tallow, lard, rice bran oil, coconut oil, flaxseed oil, palm oil, shea butter, shea butter, mango oil, and mixtures thereof.

[0081] As used herein, the term "fatty acid" refers to molecules derived from triglycerides, including carboxylic acids with long aliphatic tails (chains), which can be saturated or unsaturated. When not attached to other molecules, they are called "free" fatty acids. Most naturally occurring fatty acids have chains with an even number of carbon atoms, ranging from 4 to 28. Short-chain fatty acids (SCFAs) are fatty acids with aliphatic tails of fewer than six carbon atoms. Medium-chain fatty acids (MCFAs) are fatty acids with aliphatic tails of 6–12 carbon atoms, which can form medium-chain triglycerides. Long-chain fatty acids (LCFAs) are fatty acids with aliphatic tails of 13 to 21 carbon atoms. Very long-chain fatty acids (VLCFAs) are fatty acids with aliphatic tails longer than 22 carbon atoms. In one instance, a fatty acid or its ester may include at least 10, at least 12, at least 14, at least 16, at least 18, or at least 20 carbon atoms. In certain specific instances, fatty acids or their esters may contain 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, or 45 carbon atoms, wherein any of these values ​​may be used as an upper or lower limit where appropriate. In other instances, glycerides may comprise mixtures of fatty acids or their esters with different carbon atom ranges.

[0082] In a preferred embodiment, the lipid portion of the monoester glycolipid has a carbon chain length in the range of C6-C26, and can be saturated or unsaturated. The unsaturated portion has 1-6 double bonds, preferably 1-3 double bonds, such as 1-2 double bonds. More preferably, the carbon chain length is in the range of C10-C18. Even more preferably, the carbon chain length is in the range of C16-C18.

[0083] In one or more embodiments, the monoester glycolipid or mixture of monoester glycolipids includes a carbohydrate portion, said carbohydrate portion being maltose, and said monoester glycolipid includes a lipid portion derived from diglycerides and / or triglycerides selected from sunflower seed oil.

[0084] In one or more embodiments, the monoglyceride glycolipid or mixture of monoglycerides comprises a carbohydrate moiety, said carbohydrate moiety being maltose, and wherein the lipid moiety of said monoglyceride glycolipid has a carbon chain length in the range of C6-C26, and may be saturated or unsaturated, the unsaturated moiety having 1-6 double bonds. More preferably, the carbon chain length is in the range of C10-C18. More preferably, the carbon chain length is in the range of C16-C18.

[0085] In one or more embodiments, the monoglyceride glycolipid or mixture of monoglycerides comprises a carbohydrate portion, said carbohydrate portion being maltose, and said monoglyceride glycolipid comprises a lipid portion derived from diglycerides and / or triglycerides selected from the following sources: sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, tallow, lard, rice bran oil, coconut oil, mango oil, Kalahari seed oil, almond oil, poppy seed oil, plum kernel oil, grape seed oil, apricot kernel oil, flaxseed oil, palm oil, shea butter, shea butter, and mixtures thereof, preferably derived from sunflower oil.

[0086] The third aspect relates to a method for cleaning textiles and / or textile articles, comprising the following steps:

[0087] - Provides a laundry detergent composition comprising monoester glycolipids or a mixture of monoester glycolipids, wherein the concentration is such that it effectively cleans fabrics / textile articles under predetermined washing conditions;

[0088] - At one or more points during the washing process, one or more textiles and / or textile articles are brought into contact with the laundry detergent composition; and

[0089] - Allow the textiles and / or textile articles to dry, or to be mechanically tumble dried.

[0090] Another aspect of the present invention relates to a process for producing monoester glycolipids, the process comprising the following steps:

[0091] (i) In a reaction vessel, the carbohydrates are dispersed and / or dissolved in a polar organic solvent;

[0092] (ii) Add diglycerides and / or triglycerides to the reaction vessel to form a starting mixture;

[0093] (iii) Disperse the lipase in the starting mixture under stirring;

[0094] (iv) At a temperature between 0 and 100 degrees Celsius, the carbohydrate is subjected to transesterification with the diglyceride and / or triglyceride to form a first liquid fraction and a first solid fraction, the first liquid fraction comprising the polar organic solvent, monoglycerides, glycerol, and monoglycerides, diglycerides, and / or triglycerides, and the first solid fraction comprising lipase and optionally unreacted carbohydrates.

[0095] (v) Separating the first liquid fraction from the first solid fraction; and

[0096] (vi) Separating monoglycerides from the first liquid fraction to form a second liquid fraction, the second liquid fraction comprising monoglycerides, diglycerides and / or triglycerides and glycerol.

[0097] The core concept involves using lipases to catalyze transesterification between carbohydrates and diglycerides and / or triglycerides to form monoglycerides and glycerides with one less fatty acid bound (i.e., monoglycerides or diglycerides, respectively). Depending on the type of lipase, diglycerides (diacylglycerols) can act as substrates to undergo a new reaction with another carbohydrate molecule to form monoglycerides and monoglycerides. Similarly, depending on the lipase used, monoglycerides (monoacylglycerols) can act as substrates to undergo a new reaction with another carbohydrate molecule to form monoglycerides and glycerols. In this context, the term "transesterification" refers to a chemical reaction in the presence of a catalyst (i.e., a lipase) in which the alkoxy group of an ester compound, namely diglycerides and / or triglycerides (and optionally subsequently formed monoglycerides), is exchanged with another alkoxy group through the reaction of the ester with an alcohol (i.e., a carbohydrate).

[0098] Because each lipase has different specificities for fatty acids, it is important to select the appropriate lipase based on the type of fatty acids in the glycerol ester. If non-regional specificity (i.e., all fatty acids can be cleaved / transferred from the glycerol ester) is required, then a non-regional specific lipase should be selected. Suitable examples include, for instance, Candida antarctica type B lipase, lipase OF (from Candida rugosa), lipase G (from Penicillium camembertii), lipase AYS (from Candida rugosa), lipase PS (from Burkholderia cepacia), lipase AK (from Pseudomonas fluorescens), lipase AS (from Aspergillus niger), and lipase M (from Mucor javanicus). If region specificity (i.e., only some fatty acids can be cleaved / transferred from the glycerol ester) is required, then a region-specific lipase should be selected. Suitable examples of 1,3-region specificity could be, for example, lipase F-AP15 (derived from Rhizopus oryzae), lipase Newlase F3G (derived from Rhizopus niveus), lipase R (derived from Penicillium roqueforti), Lipozyme RM-IM (derived from Rhizomucormiehei), Lipozyme TL-IM (derived from Thermophilus sparsely cottony), and pancreatic lipase (derived from porcine pancreas).

[0099] In one or more embodiments, the lipase is selective for position 1, position 3, or both of the glycerol ester.

[0100] In one or more embodiments, the lipase selective for position 1, position 3, or both is selected from: *Chromobacterium viscosum*, canine gastric lipase, canine pancreatic lipase, *Fusarium solani* cutinase lipase, guinea pig pancreatic lipase, human gastric lipase, *Potassium spp.* lipase, human pancreatic lipase, lipoprotein lipase, *Mucor miehei* lipase, *Pseudomonas aeruginosa* lipase, *Penicillium carmenii* lipase, *Pseudomonas fluorescens* lipase, *Pseudomonas glumae* lipase, porcine pancreatic lipase, *Penicillium simplicissimum* lipase, *Rhizopus arrhizus* lipase, rabbit gastric lipase, *Fusarium heterosporum* lipase, *Candida pumilum* lipase, and variants thereof.

[0101] In one or more embodiments, the lipase is non-selective for position in the glycerol ester.

[0102] In one or more embodiments, the process further includes step (vii): separating monoglycerides, diglycerides, and / or triglycerides from the second liquid fraction.

[0103] Monoglycerides are used as emulsifiers in a variety of foods, such as whipped cream, baked goods, and ice cream.

[0104] In one or more embodiments, the lipase is selective for the 1- and 3-positions of the glycerol ester, and the process further includes step (vii): separating the formed glycerol monoester from the second liquid fraction.

[0105] Diglycerides are common food additives used to blend certain ingredients, such as oils and water. In addition, both monoglycerides and diglycerides are recommended as shortening and shelf-life extenders in baking margarine and shortening. They are also used as shortening agents in ice cream and imitation creams.

[0106] In one or more embodiments, a triglyceride is added to the reaction vessel, wherein the lipase is selective for the 1-position of the glyceride, and the process further includes step (vii): separating the formed diglyceride from the second liquid fraction.

[0107] In one or more embodiments, triglycerides are added to the reaction vessel, wherein the lipase is selective for the 1,3 position of the glycerides, and wherein the process further includes step (vii): separating the formed diglycerides from the second liquid fraction.

[0108] It is foreseeable that the aforementioned lipase specificity (saturated / unsaturated specificity and 1,3-position specificity) is high at low conversion rates, and decreases as preferred substrates are consumed and less preferred substrates are simultaneously added. Therefore, it is preferable to carry out the reaction at low conversion rates to ensure the highest possible specificity. In some embodiments of the invention, it is advantageous to fully utilize all reaction products even at low transesterification conversion rates.

[0109] In one or more embodiments, the present invention relates to a process in which the transesterification conversion to monoglycerides and monoglycerides or diglycerides is less than 5%, less than 10%, less than 15%, less than 20%, less than 25%, less than 30%, less than 35%, less than 40%, less than 45%, or less than 50%.

[0110] In one or more embodiments, the present invention relates to a process in which the transesterification of the product into monoglycerides and monoglycerides or diglycerides is at a conversion rate of at least 40%, at least 45%, at least 50%, at least 55%, at least 60%, at least 65%, or at least 70%.

[0111] In one or more embodiments, the present invention relates to a process in which the lipase is selective for saturated fatty acids, preferably selected from Candida antarcticis lipase A, Fusarium oxysporum lipase and its variants.

[0112] The separation method for purifying monoglycerides or diglycerides from the first liquid fraction may be selected from deodorization, distillation, evaporation, or any combination thereof. The presence of fatty acid esters or free fatty acids can be removed as a volatile fraction by deodorization, evaporation, or distillation. This volatile fraction can be further separated into alcohols (optionally for reuse in step (I)) and unreacted free fatty acids or fatty acid esters, which can be reused in step (VI). Deodorization is essentially steam distillation under vacuum, as is well known in the art. The deodorizer can be operated at 0.15 mbar, 225 °C, with a steam addition rate of 0.20% to 0.25% w / w per hour. Other operating modes are also known in the art, for example, see “Introduction to Fats and Oil Technology,” Eds O'Brien, Farrr and Wan, AOCS Press, Chapter 13, 2000.

[0113] Methods of distillation and evaporation are also known in the art. Evaporation apparatus for oils is typically a steam distillation unit, referred to as a deodorizer. For step (VIII), high-vacuum distillation is one implementation method to minimize thermal damage. In some embodiments of the invention, a system with multiple equilibration stages is preferred to achieve good separation. Other preferred embodiments include falling film molecular distillers operating at pressures of 0.001 to 10 mmHg and temperatures of 140–200 degrees Celsius, or centrifugal molecular distillers that can operate at pressures of approximately 0.001–10 mmHg and temperatures of 160–240 degrees Celsius (both modes are described in detail in Batistella et al., Appl. Biotechn., vol. 98, 1149–1159, 2002). Direct or indirect heating can be used, and operation can be carried out intermittently and / or continuously.

[0114] Preferably, the transesterification can be carried out at a temperature in the range of 20-95 degrees Celsius, depending on the optimal conditions for the lipase to function, such as in the range of 30-85 degrees Celsius, for example in the range of 40-75 degrees Celsius, such as in the range of 50-65 degrees Celsius, for example at about 60 degrees Celsius.

[0115] The time period for transesterification is preferably in the range of several minutes, such as five minutes, to several hours, such as 120 hours, depending on the reaction time of the reactants used.

[0116] The preferred solvents for transesterification reactions are: tert-amyl alcohol, acetone, tert-butanol, 1-propanol, isopropanol, isobutanol, and isoamyl alcohol.

[0117] The resulting glycolipids can be purified by standard methods, such as extraction, filtration through mesoporous adsorbents or membranes, chromatography using various solvents based on affinity or adsorption, distillation of any residual volatile solvents, and separation of precipitated products, byproducts, or reactants by centrifugation.

[0118] Solvents suitable for chromatography can be, for example, water, methanol, ethyl acetate, ethanol, pentane, hexane, heptane, acetone, methyl ethyl ketone, dichloromethane, tert-amyl alcohol, and 1-propanol.

[0119] The method for producing monoester glycolipids disclosed in this invention is an exemplary, but preferred, method. Other methods are also covered in this invention.

[0120] On the other hand, it relates to monoester glycolipids produced by the process according to the invention.

[0121] It also relates to monoglycerides and / or diglycerides produced by the process of the present invention.

[0122] It should be noted that the embodiments and features described in the context of one aspect of the invention are also applicable to other aspects of the invention.

[0123] Example

[0124] Example 1 - Production of Monoester Glycolipids

[0125] Monosaccharides or disaccharides were added to a stirred vessel with a selected solvent to prepare a 10% w / w dispersion. Oil was then added under stirring to achieve a 1:1 molar ratio of oil to sugar. Lipase was added at a concentration of 10% w / w (relative to the mass of sugar). The reaction mixture was heated to 60°C and stirred for 120 hours. Product formation was detected by TLC analysis and subsequently purified by column chromatography using elution with DCM:MeOH.

[0126] Examples of solvents tested and used: tert-amyl alcohol, acetone, tert-butanol, 1-propanol, isopropanol, isobutanol, and isoamyl alcohol.

[0127] Examples of lipases tested and used: Candida antarcticis type B lipase, Lipozyme RM-IM (derived from Rhizopus miltiorrhiza), and Lipozyme TL-IM (derived from Thermophilus sparsely cottony).

[0128] Monoester glycolipids have been synthesized based on maltose, sucrose, cellobiose, trehalose, galactose, and glucose. Another reactant was selected from sunflower oil, rapeseed oil, olive oil, frying oil (i.e., a mixture of sunflower oil, rapeseed oil, and corn oil), and shea butter. Experiments were unsuccessful when xylose and lactose were used as carbohydrates.

[0129] This indicates that not all sugars exhibit the same behavior, despite having similar or identical chemical compositions, which is well-known among carbohydrates. For example, maltose, sucrose, and lactose all share the same composition (C... 12 H 22 O 11 However, among these three sugars, synthesis was successful only for sucrose and maltose.

[0130] Monoester glycolipids synthesized based on monosaccharides (glucose and galactose) have extremely low solubility in water and therefore cannot be used for subsequent tests in the following examples.

[0131] Example 2 - Comparison of Laundry Detergent Compositions

[0132] A series of four laundry detergent compositions were prepared, each containing only one different ingredient. Three different commercially available nonionic surfactants (#1, #3, and #4) were selected for comparative testing with the monoester glycolipid (#2, SBS1) according to the present invention.

[0133] SBS1 is a monoester glycolipid with maltose as its carbohydrate moiety and oleic acid (6- and / or 6'-oleoyl-maltose) as its lipid moiety.

[0134] D-glucopyranose, oligomers, and decyl octyl glycosides are available under the trade name Triton CG-110. Triton CG-110 is a nonionic surfactant used in laundry detergent compositions and is known for its mildness. Its chemical class is also known as alkyl polyglucoside.

[0135] Secondary alcohol (C12-C14) ethoxylated compounds 31EO are available under the trade name Tergitol 15-S-30. Tergitol 15-S-30 is a nonionic surfactant commonly used in various applications, including laundry detergents. Tergitol 15-S-30 is a mixture of C12-14 secondary alcohols ethoxylated to an average of 31 ethylene oxide (EO) units.

[0136] Decaethylene glycol monododecyl ether belongs to the category of nonionic surfactants and is commonly used in laundry detergent compositions. It is formed by the ethoxylation of dodecyl alcohol with ethylene oxide, resulting in a molecule with ten ethylene oxide units (hence the name "decanediol"). This structure endows it with unique surface-active properties.

[0137]

[0138]

[0139] The detergency, wetting, foaming and emulsifying abilities of different detergents were tested.

[0140] Cleaning power

[0141] method

[0142] The detergency test consisted of the following steps: A fabric sample was stained with sunflower oil and then cleaned using the formula. The fabric sample was cut into 7x7 cm pieces. 10 mL of sunflower oil was diluted to 100 mL with dichloromethane. At room temperature, the fabric sample was folded and immersed in the solution for 5 minutes, then unfolded and dried overnight. The fabric sample was weighed before and after staining to determine the amount of oil deposited. Cleaning was performed using 1000 mL of cleaning solution, which was prepared by diluting 50 mL of detergent formula with deionized water to 1000 mL (approximately 1% total surfactant). Four fabric samples were cleaned simultaneously in the same chamber as a repeat experiment. At room temperature, the stirring speed was set to 200 rpm, and the cleaning time was 20 minutes. After the cleaning cycle, the sample was immediately rinsed with 1000 mL of deionized water at room temperature for 10 minutes. The detergency was measured after the cleaned fabric sample was completely dry. Detergent efficiency is expressed as a percentage of oil removal; a higher value indicates better detergency.

[0143] result

[0144]

[0145] Formulations containing monoester glycolipids (#2, SBS1) outperformed formulations with commercial surfactants on cotton fabrics and were equally effective on cotton / polyester blends.

[0146] foaming

[0147] method

[0148] Foaming ability and stability were measured by mixing and determining the foam height at t=1 and t=30 min. For this test, 5 mL of the desired surfactant formulation was used in triplicate in a 1:200 dilution (approximately 0.1% total surfactant). The sample was added to a 15 mL centrifuge tube with a screw cap. Foaming was initiated by manually shaking the tube for 10 sec and then allowing it to stand for 50 sec. The foam height was measured at time = 1 min, which represents the foaming ability. The sample was then allowed to stand, and the foam height was measured again at time = 30 min. Foam stability was determined by the ratio of the foam height at time = 1 min to that at time = 30 min.

[0149] result

[0150]

[0151]

[0152] Formulations containing monoester glycolipids (#2, SBS1) exhibited comparable performance to formulations containing commercially available surfactants. Laundry detergents generally prefer relatively low foaming properties. The compound used in formulation #1 is considered a low-foaming surfactant.

[0153] Emulsification Index - E24

[0154] method

[0155] The emulsification index (E24) is measured to determine the formulation's ability to dissolve hydrocarbons by mixing the surfactant formulation with oil and measuring the height of the emulsion. For the test, 5 mL of a 1:200 water dilution of the surfactant formulation (approximately 0.1% of total surfactant) and 5 mL of paraffin oil (low viscosity), sunflower oil, olive oil, or frying oil are added to a 15 mL centrifuge tube. The test is performed in triplicate. The tube is manually shaken for 10 seconds at room temperature to mix the formulation dilution, and then allowed to stand at room temperature. E24 is defined as the ratio of the height of the emulsion to the total volume height 24 hours after mixing. For palm oil (refined), a similar procedure is used, but the solid palm oil is first heated to 40 degrees Celsius to melt it. After mixing, the sample is allowed to stand at a constant temperature of 35 degrees Celsius for 24 hours, and then E24 is measured as described above.

[0156] result

[0157]

[0158] Formulations containing monoester glycolipids (#2, SBS1) outperformed or were equivalent to formulations containing commercial surfactants.

[0159] Draves Test - Wetting Ability

[0160] method

[0161] Wetting ability is measured by the time required for cotton skein to sink into a surfactant solution. Good wetting ability helps water adhere to the fabric surface, expel air, and facilitates the removal of oil and dust from the surface. The faster the sinking time, the better the wetting ability. For testing, each surfactant formulation is prepared as a 1:200 water dilution (approximately 0.1% of total surfactant). 600 mL of the dilution is loaded into a graduated cylinder, and 5 g of 100% cotton skein is attached to a hook and a weight with a rope, then immersed in the solution. The time required for the rope to relax is defined as the wetting time. The test is performed in triplicate.

[0162] result

[0163]

[0164] Formulations containing monoester glycolipids (#2, SBS1) showed better performance than formulations containing commercial surfactants.

[0165] Breakthrough test - wetting ability

[0166] method

[0167] Wetting ability is measured by the time required for a single drop of surfactant formulation to penetrate the oil film. The sunflower oil used for testing was first dyed red to better visualize the breakthrough point. This was done by adding 0.05% w / w OilRed O to the oil and stirring for 1 hour to ensure uniform dye distribution. The test uses... Small crystallization dishes were prepared in triplicate. For each test, 35g of water was poured into the dish first. Then, 2.5g of dyed oil was slowly added on top to form a thin dish. Using a pipette, 5µL of a 1:1 diluted formulation (approximately 10% total surfactant) droplet was carefully deposited in the center of the oil disc. Breakthrough time was measured from deposition to the cracking of the oil disc.

[0168] result

[0169]

[0170] Formulations containing monoester glycolipids (#2, SBS1) exhibited effects comparable to those containing commercial surfactants.

[0171] Example 3 - Comparison of Laundry Detergent Compositions

[0172] Three additional laundry detergent compositions were prepared using glycolipids. Again, these compositions differed from each other by only one component and were composed of similar components to those in the formulation of Example 2. Three additional monoester glycolipid compositions (#5SBS2, #6SBS3, and #7SBS4) were compared with commercial nonionic surfactant formulations (#1, #3, and #4) along with #2 (SBS1). SBS2 is a monoester glycolipid with a carbohydrate moiety of sucrose and a lipid moiety of oleic acid (6- and / or 6'-oleoyl-sucrose). SBS3 is a monoester glycolipid with a carbohydrate moiety of trehalose and a lipid moiety of oleic acid (6- and / or 6'-oleoyl-trehalose). SBS4 is a monoester glycolipid with a carbohydrate moiety of cellobiose and a lipid moiety of oleic acid (6- and / or 6'-oleoyl-cellobiose).

[0173]

[0174]

[0175] Emulsifying ability

[0176] method

[0177] Emulsifying capacity is measured by determining the formulation's ability to dissolve hydrocarbons through mixing the surfactant formulation with oil and measuring the height of the emulsion. For the test, 1 mL of a 1:200 water dilution of the surfactant formulation (approximately 0.1% of the total surfactant) and 1 mL of sunflower oil, corn oil, or rapeseed oil are added to a 4 mL screw-capped vial. The test is performed in triplicate. The formulation dilution is vortexed for 20 seconds and allowed to stand at room temperature. Emulsifying capacity is determined by the ratio of emulsion height to total volume height after 10 min, 1 hour, 2 hours, and 3 hours of mixing.

[0178] result

[0179]

[0180]

[0181] Four formulations containing monoester glycolipids #2 (SBS1), #5 (SBS2), #6 (SBS3), and #7 (SBS4) exhibited performance comparable to formulations containing commercial surfactants. Furthermore, despite significant differences in the solubility of disaccharides themselves, monoester glycolipids derived from maltose, trehalose, and cellobiose performed comparably to those derived from sucrose.

[0182] Example 4 - Effects of different amounts of nonionic surfactant

[0183] A series of four laundry detergent compositions were prepared to test the effects of different concentrations of nonionic surfactant when replacing anionic surfactants. This was achieved by replacing a portion of the LAS (sodium dodecylbenzenesulfonate, an anionic surfactant) present in the compositions described earlier in Examples 1 and 2 with a commercially available alkyl polysaccharide glycoside (APG) (Triton CG-110) or a monoester glycolipid (#2, SBS1) according to the invention. Increased concentrations were achieved by reducing / replacing LAS by 30% (#8 and #9) and by reducing / replacing LAS by approximately 60% (#10 and #11).

[0184]

[0185] Using the same approach as described in Example 2, the detergency, wetting, foaming, and emulsifying abilities of different formulations were tested.

[0186] Cleaning power

[0187] result

[0188]

[0189] When the nonionic surfactant was increased by 30%, monoester glycolipid (SBS1) showed comparable detergency to commercial APG (Triton CG-110). However, when the nonionic surfactant was increased by 60%, the detergency of the monoester glycolipid (SBS1) formulation was superior to that of commercial APG (Triton CG-110) on both 100% cotton and cotton / polyester blends.

[0190] foaming

[0191] result

[0192]

[0193] Whether the nonionic surfactant content is increased by 30% or 60%, monoester glycolipid (SBS1) outperforms commercial nonionic APG (Triton CG-110) because laundry detergents should preferably have relatively low foaming.

[0194] Emulsification Index - E24

[0195] result

[0196]

[0197]

[0198] When the nonionic surfactant was increased by 30%, monoester glycolipid (SBS1) exhibited comparable emulsifying ability to commercial APG (Triton CG-110). When the concentration was increased to 60%, the monoester glycolipid (SBS1) formulation showed better emulsifying performance than commercial APG (Triton CG-110).

[0199] Draves Test - Wetting Ability

[0200] result

[0201]

[0202] Wetting time showed that, compared with monoester glycolipid (SBS1), commercial APG (Triton CG-110) exhibited slightly better wetting ability in both formulations with 30% and 60% increases in nonionic surfactant concentration, respectively.

[0203] Example 5 - Enzyme Activity

[0204] Lipolysis activity was monitored using a chromogenic precursor substrate for nitrophenylbutyrate. Briefly, a mixture of different surfactants and lipases was placed in a buffer solution of 50 mM Tris, 50 mM NaCl, and pH 8, resulting in an enzyme concentration of 10 nM. The mixture was incubated at 25°C for 10 min prior to analysis to ensure temperature stability. Then, a stock solution of 15 mM was injected into the substrate to bring the final concentration to 0.12 mM. The release of the chromogenic product was monitored for several minutes by measuring absorbance at 405 nm using a Clariostar microplate reader (BMG LABTECH, Ortenberg, Germany). The resulting slope within the linear range was determined by linear regression to determine enzyme activity, which was then normalized relative to the activity of lipases in the buffer solution. Triples of experiments were performed. The enzyme used was from a commercially available formulation. The lipase was extracted from 200L (Novozymes) and is used in the formulation of laundry detergent. The lipase was purified using dialysis and ion exchange chromatography (to ensure that the interaction is only between the surfactant and the enzyme). 200L belongs to a variant of the *Pseudomonas aeruginosa* lipase family. The surfactants used are shown in the table below, and the results are... Figure 1 Shown in.

[0205] surfactants Names in the chart Secondary alcohol (C12-C14) ethoxylate 31EO C12E31 SBS1 SBS1 Decaethylene glycol monododecyl ether C12E10 D-glucanopyranose, oligomers, decyl octyl glycoside Triton APG Cocamidopropyl Betaine Cocamidopropyl Betaine

[0206] The normal concentration of surfactants during the washing process is at least 200 mg / L. Data shows that even in the presence of small amounts of surfactant, enzymes lose activity. Most commercially available surfactants tested retained only 5-10% of their lipase activity at concentrations above 200 mg / L. Triton APG, calculated by interpolation, showed 70% lipase activity at 200 mg / L, but its activity rapidly declined at higher concentrations. Monoester glycolipids (SBS1) unexpectedly boosted lipase activity at concentrations of 100 mg / L and above, outperforming Triton APG (interpolated value) at approximately 800 mg / L. This suggests that monoester glycolipids (SBS1) are a better choice for future laundry detergents for washing machines that utilize less water than existing machines. Furthermore, the fact that SBS1 can still relatively boost lipase activity at higher concentrations indicates that SBS1 is mild on enzymes and is likely compatible with other enzymes that can be used in laundry detergent formulations, such as proteases, amylases, and cellulases.

Claims

1. Use of monoester glycolipids or mixtures of monoester glycolipids in laundry detergent compositions; characterized in that, The monoester glycolipid or mixture of monoester glycolipids includes the carbohydrate portion selected from the group consisting of maltose, cellobiose, trehalose, isomaltulose, lactulose, isomaltose, and mixtures thereof.

2. The use according to claim 1, wherein, The disaccharide is derived from polysaccharides, such as starch, for example, through enzymatic cleavage.

3. The use according to claim 1, wherein, The monoester glycolipid or mixture of monoester glycolipids includes the carbohydrate portion selected from the group consisting of maltose, cellobiose, trehalose, and mixtures thereof.

4. The use according to claim 1, wherein, The monoester glycolipid or mixture of monoester glycolipids includes a carbohydrate portion, which is maltose.

5. The use according to any one of claims 1-4, wherein, The monoglycerides comprise lipid fractions of diglycerides and / or triglycerides derived from sources selected from the following: sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, tallow, lard, rice bran oil, coconut oil, flaxseed oil, mango oil, Kalahari seed oil, almond oil, poppy seed oil, plum kernel oil, grape seed oil, apricot kernel oil, palm oil, shea butter, shea butter, and mixtures thereof.

6. The use according to any one of claims 1-4, wherein, The monoester glycolipid includes a lipid moiety having a chain length in the range of C6-C26, the lipid moiety being saturated or unsaturated with 1-6 double bonds, such as oleic acid and / or linoleic acid and / or stearic acid and / or palmitic acid and / or trans-palmitoyl oleate and / or palmitoleic acid.

7. The use according to any one of claims 1-4, wherein, The monoester glycolipid includes a lipid moiety having a chain length in the C16-C18 range, the lipid moiety being saturated or unsaturated with 1-6 double bonds, such as oleic acid and / or linoleic acid and / or stearic acid and / or palmitic acid and / or trans-palmitoyl oleate and / or palmitoleic acid.

8. A laundry detergent composition comprising: - A monoester glycolipid or a mixture of monoester glycolipids; characterized in that the monoester glycolipid or the mixture of monoester glycolipids comprises a carbohydrate portion selected from the group consisting of maltose, cellobiose, trehalose, isomaltulose, lactulose, isomaltose and mixtures thereof.

9. The laundry detergent composition according to claim 8, further comprising: - One or more enzymes.

10. The laundry detergent composition according to claim 9, wherein, The enzyme in question is a lipase.

11. The laundry detergent composition according to claim 10, wherein, The lipase is derived from strains of Thermomyces lanuginosus (TLL) or variants thereof.

12. The laundry detergent composition according to any one of claims 8-11, wherein, The monoester glycolipid or mixture of monoester glycolipids includes the carbohydrate portion selected from the group consisting of maltose, sucrose, lactose, cellobiose, trehalose, and mixtures thereof.

13. The laundry detergent composition according to any one of claims 8-11, wherein, The monoester glycolipid or mixture of monoester glycolipids includes a carbohydrate portion, which is maltose.

14. The laundry detergent composition according to any one of claims 8-13, wherein, The monoglyceride glycolipids comprise lipid fractions derived from diglycerides and / or triglycerides selected from the following sources: sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, tallow, lard, rice bran oil, coconut oil, mango oil, Kalahari seed oil, almond oil, poppy seed oil, plum kernel oil, grape seed oil, apricot kernel oil, flaxseed oil, palm oil, shea butter, shea butter, and mixtures thereof, preferably derived from sunflower oil.

15. The use according to any one of claims 8-13, wherein, The monoester glycolipid includes a lipid moiety having a chain length in the range of C6-C26, the lipid moiety being saturated or unsaturated with 1-6 double bonds, such as oleic acid and / or linoleic acid and / or stearic acid and / or palmitic acid and / or trans-palmitoyl oleate and / or palmitoleic acid.

16. The use according to any one of claims 8-13, wherein, The monoester glycolipid includes a lipid moiety having a chain length in the C16-C18 range, the lipid moiety being saturated or unsaturated with 1-6 double bonds, such as oleic acid and / or linoleic acid and / or stearic acid and / or palmitic acid and / or trans-palmitoyl oleate and / or palmitoleic acid.

17. A method for cleaning textiles and / or textile articles, comprising the following steps: - Provides a laundry detergent composition comprising monoester glycolipids or a mixture of monoester glycolipids, wherein the concentration is such that it effectively cleans fabrics / textile articles under predetermined washing conditions; - At one or more points during the washing process, one or more textiles and / or textile articles are brought into contact with the laundry detergent composition; and - Allow the textiles and / or textile articles to be dried, or to be mechanically tumble-dried; characterized in that the monoester glycolipid or mixture of monoester glycolipids comprises a carbohydrate portion selected from the group consisting of maltose, cellobiose, trehalose, isomaltulose, lactulose, isomaltose and mixtures thereof.

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