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. Monoester glycolipids or mixtures of monoester glycolipids include a carbohydrate portion selected from the group consisting of maltose, cellobiose, trehalose, isomaltulose, lactulose, isomaltose, and mixtures thereof.

Description

Technical Field

[0001] The present invention relates to a laundry detergent.

Background Art

[0002] A laundry detergent is a composition used during the cleaning process of fibers / laundry to remove unwanted substances therefrom. One of the most important groups of compounds in laundry detergents is surfactants, also called surface-active agents. Surfactants contain a hydrophilic part and a hydrophobic part, which makes them suitable for diffusing in water and adsorbing at the interface between water and unwanted substances on the fibers. Somewhat simplified, here the surfactant molecules arrange around the unwanted substances and surround them, thereby releasing them from the fibers and forming micelles with the unwanted substances inside.

[0003] By changing either the hydrophilic part and / or the hydrophobic part, properties such as wettability, foaming ability, and dispersibility can be adjusted. Thereby, surfactants have different abilities to remove specific types of unwanted substances, effectiveness against different types of fibers, and reactions to water hardness.

[0004] The surfactants currently in use have been shown to be very effective. However, the consumers' demand for milder and "more environmentally friendly" new laundry detergents means that it is necessary to address this field again.

Summary of the Invention

[0005] Therefore, an object of the present invention is to provide an environmentally friendly detergent as an alternative to currently used laundry detergents.

[0006] The inventors of the present invention have found the use of a new subtype of environmentally friendly nonionic surfactant, monoester glycolipid, as an alternative to conventional nonionic surfactants for laundry detergents.

[0007] The inventors of this invention have also found a process for producing monoester glycolipids from renewable resources such as enzymatically cleaved starch (e.g., maltose) and used cooking oils (e.g., sunflower oil, rapeseed oil, corn oil, and olive oil). Furthermore, these monoester glycolipids are biodegradable. Some of the by-products (monoglycerides and diglycerides) can even be isolated as valuable food components 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] A second aspect relates to a laundry detergent composition comprising a monoester glycolipid or a mixture of monoester glycolipids.

[0010] A third aspect relates to a method for washing fibers and / or textile articles, the method being: - A step of providing a laundry detergent composition comprising a monoester glycolipid or a mixture of monoester glycolipids in a concentration for effectively washing fabrics / textiles under specified washing conditions. The steps of bringing one or more fibers and / or textile articles into contact with a laundry detergent composition at one or more points in the washing process, and The process includes the step of drying or mechanically tumble-drying the fibers and / or textile articles.

[0011] The present invention will be described in more detail below. [Brief explanation of the drawing]

[0012] [Figure 1] Figure 1 shows the results of Example 5. [Modes for carrying out the invention]

[0013] Glycolipids are amphoteric, anionic, cationic, or nonionic molecules containing a hydrophilic carbohydrate moiety and one or more fatty acids as a lipophilic moiety. Monoester glycolipids have a single fatty acid as the lipophilic moiety. The inventors of this invention have also found that monoester glycolipids have properties comparable to, and sometimes better than, several conventional nonionic surfactants produced from petrochemicals and palm oil (see the Experiments section for selection of results).

[0014] The first aspect relates to the use of monoester glycolipids or mixtures of monoester glycolipids in laundry detergent compositions.

[0015] A second aspect relates to a laundry detergent composition comprising a monoester glycolipid or a mixture of monoester glycolipids.

[0016] The inventors of this invention have discovered a process for producing monoester glycolipids from renewable resources.

[0017] The laundry detergent composition of the present invention can take any of many forms. It can take the form of a dilutable laundry detergent, a liquid with a surfactant structure, granules, spray-dried or dry blended powder, tablets, pastes, molded solids, or any other laundry detergent known to those skilled in the art.

[0018] For the purposes of this disclosure, a “dilutable laundry detergent” composition is defined as a product intended to be used by being diluted with water in a ratio greater than 100:1 to produce a liquid suitable for washing fabrics. Water-soluble sheets or pouches, such as those described in U.S. Patent Application No. 20020187909, are also envisioned as possible embodiments of the present invention. These may be marketed under various names for various purposes.

[0019] How to use The following details a method for cleaning fibers and / or textile articles, including the following steps in no particular order: i. providing a laundry detergent composition comprising a monoester glycolipid or a mixture of monoester glycolipids at a concentration effective to effectively wash fabrics and / or textile articles under predetermined washing conditions; ii. contacting one or more fibers and / or textile articles with the laundry detergent composition at one or more points during the washing process; and iii. drying the fibers and / or textile articles or mechanically tumble drying them.

[0020] The amount of the laundry detergent composition used generally ranges from about 10 g to about 300 g of the total product per 3 kg of textile articles, depending on other factors such as consumer preferences that affect the specific embodiments selected and the usage behavior of the product.[[ID=⑨]]

[0021] Consumers using the present invention may also be specifically instructed to contact textile articles such as clothing with the composition of the present invention for the purpose of simultaneously washing and softening the textile articles. This approach is recommended when the composition takes the form of a softening detergent administered at the start of the washing cycle.

[0022] In addition to the monoester glycolipids described above, formulators may include one or more optional components in the laundry detergent composition. These components are not necessary for practicing the present invention, but the use of such materials is often very helpful in making the formulation of the laundry detergent composition acceptable for consumer use.

[0023] Examples of optional components include, but are not limited to, anionic surfactants, nonionic surfactants, amphoteric and zwitterionic surfactants, cationic surfactants, hydrotropes, fluorescent whitening agents, optical bleaching agents, fiber lubricants, reducing agents, enzymes, enzyme stabilizers, powder finishers, defoamers, builders, bleaches, bleach catalysts, soil release agents, anti-redeposition agents, dye transfer inhibitors, buffers, colorants, fragrances, profragrances, rheology modifiers, anti-ashing polymers, preservatives, insect repellents, soil repellents, water repellents, suspending agents, aesthetic agents, structuring agents, bactericides, solvents, fabric finishers, dye fixatives, wrinkle reducers, fabric conditioners, and deodorants.

[0024] In one or more embodiments, the laundry detergent composition further comprises one or more enzymes.

[0025] The laundry detergent composition may further comprise one or more enzymes that provide cleaning performance and / or fabric care effects. The enzymes may include cellulase, hemicellulase, peroxidase, protease, glucoamylase, amylase, lipase, cutinase, pectinase, xylanase, mannanase, pectate lyase, reductase, oxidase, phenol oxidase, lipoxygenase, ligninase, pullulanase, tannase, pentosanase, mannanase, β-glucanase, arabinosidase or mixtures thereof.

[0026] A preferred combination is a laundry detergent composition having a mixture of conventional applicable enzymes such as protease, amylase, lipase, cutinase and / or cellulase at a level of 50 LU to 8500 LU per liter of the cleaning solution in combination with the lipase mutant D96L.

[0027] Preferred lipases are selected from the Thermomyces lanuginosa lipase family. The Thermomyces lanuginosa lipase family refers to a group of lipase enzymes mainly derived from the thermophilic fungus Thermomyces lanuginosa. These enzymes are known for their ability to degrade lipids (fats) and have some unique characteristics such as thermal stability and substrate specificity.

[0028] Suitable cellulases include both bacterial and fungal cellulases. Preferably, they have an optimal pH between 5 and 9.5. Suitable cellulases are disclosed in U.S. Patent No. 4,435,307, which discloses a fungal cellulase produced from Humicola insolens. Suitable cellulases are also disclosed in UK Patent Publication No. 2075028(A), UK Patent Publication No. 2095275(A), and German Patent Publication No. 2247832.

[0029] An example of such a cellulase is the cellulase produced by the Humicola insolens strain (Humicola grisea var. thermoidea), particularly the Humicola strain DSM1800. Other suitable cellulases are those derived from Humicola insolens, having 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-care effects. An example of such a cellulase is the cellulase described in European Patent Application No. 91202879.2. Preferred commercially available cellulase enzymes include those sold under the trade names Celluclean®, Celluclean Classic®, and Whitezyme® by Novozymes A / S, Revitalez® by IFF, and Biotoch FLX® by AB Enzymes.

[0030] Peroxidase enzymes are used in combination with oxygen sources, such as Parkerbonate, Pervolate, Persulfate, and hydrogen peroxide. They are used in "solution bleaching," that is, to prevent the transfer of dyes or pigments removed from a substrate during a washing operation to other substrates in the washing solution. Peroxidase enzymes are known in the art and include, for example, horseradish peroxidase, ligninase, and haloperoxidases such as chloroperoxidase and bromoperoxidase. Peroxidase-containing detergent compositions are disclosed, for example, in PCT International Application WO 89 / 099813 brochure and European Patent Application 91202882.6 specification.

[0031] Cellulase and / or peroxidase are typically incorporated into laundry detergent compositions at a level of 0.0001% to 2% by weight of the active enzymes in the laundry detergent composition.

[0032] Preferred commercially available protease enzymes include those sold by Novozymes A / S under the trade names Liquanase®, Progress®, Blaze®, Alcalase®, Savinase®, Primase®, Durazym®, and Esperase®; those sold by Gist-Brocades under the trade names Maxatase®, Maxacal®, and Maxapem®; those sold by Genencor International; those sold by Solvay Enzymes under the trade names Opticlean® and Optimase®; those sold by IFF under the trade names Preferencez P® and Excelenz P®; and those sold by AB Enzymes under the trade name BIOTOUCH® ROC250LCO. Other proteases are described in U.S. Patent No. 5,679,630 and may be included in detergent compositions.

[0033] Protease enzymes may be incorporated into the detergent composition at a level of approximately 0.0001% to approximately 2% by weight of the active enzyme.

[0034] The preferred protease, referred to herein as “protease D,” is a carbonyl hydrolase mutant having an amino acid sequence not found in nature, preferably obtained by substituting an amino acid residue with a different amino acid at a position in the carbonyl hydrolase equivalent to position +76, as described in U.S. Patent No. 5,679,630, such as Bacillus amyloliquefaciens subtilisin. According to the subtilisin number, one or more amino acid residue positions equivalent to those 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 are derived from the precursor carbonyl hydrolase, the teachings thereof are incorporated herein by reference.

[0035] Among the highly preferred enzymes that can be included in detergent compositions are lipases. It has been found that the cleaning performance against fatty stains is synergistically improved by the use of lipases. Lipases are enzymes that catalyze the hydrolysis of oils and fats into fatty acids and glycerols, monoglycerides, and / or diglycerides. Suitable lipases used herein include those derived from animals, plants, fungi, and microorganisms. Suitable lipase enzymes can be found in cambium, bark, plant roots, as well as in fruits, oil palms, lettuce, rice, bran, barley and malt, wheat, oatmeal and oat flour, cotton kernels, corn, millet, coconut, walnut, fusarium, cannabis, and cucurbitaceous plant seeds. In addition to naturally occurring lipases, chemically modified or protein-engineered mutants can be used.

[0036] Suitable lipases include, for example, lipases derived from microorganisms of the Humicola group (also called Thermomyces), such as from H. lanuginosa (Thermomyces lanuginosus) or H. insolens (see, for example, PCT international application WO 96 / 13580 brochure), as described in European Patent No. 258068 and European Patent No. 305216; for example, P. alcaligenes or P. pseudoalcaligenes (see, for example, European Patent No. 218272), P. cepacia (see, for example, European Patent No. 331376), P. sutsuzeri This includes Pseudomonas lipases from P. stutzeri (e.g., British Patent No. 1,372,034), P. fluorescens, Pseudomonas sp. SD705 strain (e.g., PCT International Application WO 95 / 06720 brochure and International Publication 96 / 27002 brochure), or P. wisconsinensis (e.g., see PCT International Application WO 96 / 12012); or Bacillus lipases from, for example, B. subtilis, B. stearothermophilus, or B. pumilus (e.g., see PCT International Application WO 91 / 16422 brochure).

[0037] Lipase variants, for example, those described in U.S. Patent Nos. 8,187,854, 7,396,657, and 6,156,552, may be used, and these teachings are incorporated herein by reference. Further lipase variants are described in PCT International Application Brochure WO 92 / 05249, International Publication Brochure 94 / 01541, International Publication Brochure 95 / 35381, International Publication Brochure 96 / 00292, International Publication Brochure 95 / 30744, International Publication Brochure 94 / 25578, International Publication Brochure 95 / 14783, International Publication Brochure 95 / 22615, International Publication Brochure 97 / 04079, and International Publication Brochure 97 / 07202, as well as European Patent Nos. 0407225 and European Patent Nos. 0260105.

[0038] 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 manufactured by Novozymes). Other suitable lipases are available as Lipase P Amano® (Amano Pharmaceutical). Further suitable lipases include M1 Lipase® and Lipomax® (DSM), Lumafast® (Danisco), and Preferred L (IFF). Preferred lipases include the D96L lipase variant of the natural lipase derived from Humicola lanuginosa, as described in U.S. Patent No. 6,017,871. Preferably, Humicola lanuginosa strain DSM4106 is used.

[0039] Lipase can be used at any appropriate level. Generally, lipase is present in laundry detergent compositions in amounts of 10 to 20,000 LU / g, or even 100 to 10,000 LU / g. The LU units of lipase activity are defined in International Publication No. 99 / 42566. The dosage of lipase in a washing solution is typically 0.01 to 5 mg / L of active lipase protein, more typically 0.1 to 2 mg / L of active lipase protein. In terms of weight percentage, lipase can be used in detergents at 0.00001 to 2% by weight, usually 0.0001 to 1% by weight, or even 0.001 to 0.5% by weight.

[0040] Lipase may be incorporated into the detergent in any convenient form, such as dust-free granules, a stabilized liquid, or protected (e.g., coated) particles.

[0041] For further examples of suitable lipases useful 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. Publication No. 2011 / 0212877, the teachings of which are incorporated herein by reference.

[0042] Amylase (α and / or β) may be included for the removal of carbohydrate-based stains. Suitable amylases include Terhamyl® (Novozymes), Fungamyl® (Novozymes), BAN® Amylase (Novozymes), Stainzyme Plus® (Novozymes), Amplify® (Novozymes), Achieve® (Novozymes), Preferenz S® (IFF), and Excellenz S® (IFF).

[0043] The enzymes described above may be of any suitable origin, such as plant, animal, bacterial, fungal, and / or yeast origin. See U.S. Patent No. 5,929,022, the teachings of which are incorporated herein by reference, from which much of the preceding discussion is derived. Preferred compositions may optionally contain a combination of enzymes or a single enzyme, with the amount of each enzyme generally ranging from 0.0001% to 2%.

[0044] Other enzymes and materials used in conjunction with the enzymes are described in the brochure for PCT international application WO 99 / 05242 and are incorporated herein by reference.

[0045] Builders are often added to fabric cleaning compositions to complex and remove alkaline earth metal ions, which can interfere with the cleaning performance of detergents by binding with anionic surfactants and being removed from the cleaning solution. Preferred compositions of the present invention contain builders, particularly when used as a detergent / softener combination.

[0046] Soluble builders such as alkali metal carbonates and alkali metal citrates are particularly preferred for the liquid embodiments of the present invention. However, other builders may also be used, as will be further detailed below. Often, mixtures of builders selected from those described below and others known to those skilled in the art are used.

[0047] Alkali metal and alkaline earth metal carbonates, such as those detailed in German Patent Application No. 2,321,001, published November 15, 1973, are suitable for use as builders in the compositions of the present invention. They can be supplied and used in either anhydrous form or with bound water. Sodium carbonate or soda ash are particularly useful, both of which are readily available on the commercial market and have an excellent environmental profile.

[0048] The sodium carbonate used in this invention may be natural or synthetic, and may be used in either a high-density or low-density form, depending on the needs of the formulation. Natural soda ash is generally mined as trona and further refined to the degree specified by the needs of the product in which it is used. Synthetic ash, on the other hand, is usually produced via the Solvay process or as a byproduct of other manufacturing operations, such as the synthesis of caprolactam. It may be even more useful to include a small amount of calcium carbonate in the builder formulation to form seed crystals and enhance the builder's potency.

[0049] Organic detergent builders can also be used as non-phosphorus builders in the present invention. Examples of organic builders include alkali metal citrates, succinates, malonates, fatty acid sulfonates, fatty acid carboxylates, nitrilotriacetates, oxydisuccinates, alkyldisuccinates and alkenyldisuccinates, oxydiacetates, carboxymethyloxysuccinates, ethylenediaminetetraacetates, monosuccinate tartrate, disuccinate tartrate, monoacetate tartrate, diacetate tartrate, oxidized starch, oxidized heteropolymer polysaccharides, polyhydroxysulfonates, polycarboxylates, such as polyacrylates, polymaleates, polyacetates, polyhydroxyacrylates, polyacrylate / polymaleates and polyacrylate / polymethacrylate copolymers, acrylate / maleates / vinyl alcohol terpolymers, aminopolycarboxylates and polyacetal carboxylates, as well as polyaspartates and mixtures thereof. Such carboxylates are described in U.S. Patents No. 4,144,226, 4,146,495, and 4,686,062. Alkali metal citrates, nitrilotriacetates, oxydisuccinates, acrylate / maleate copolymers, and acrylate / maleate / vinyl alcohol terpolymers are particularly preferred non-phosphorus builders.

[0050] The compositions of the present invention utilizing water-soluble phosphate builders typically contain this builder at a level of 1 to 90% by weight of the composition. Specific examples of water-soluble phosphate builders include alkali metal tripolyphosphates, sodium pyrophosphate, potassium pyrophosphate and ammonium pyrophosphate, sodium orthophosphate and potassium orthophosphate, polymeta / sodium phosphate with a degree of polymerization ranging from about 6 to 21, and salts of phytic acid. Sodium tripolyphosphate or potassium tripolyphosphate are most preferred.

[0051] However, phosphates are often difficult to incorporate, particularly into liquid products, and have been identified as potential substances that can contribute to the eutrophication of lakes and other rivers. Therefore, preferred compositions of the present invention contain phosphates at a level of less than about 10% by weight, more preferably less than about 5% by weight. The most preferred compositions of the present invention are formulated to be substantially free of phosphate builders.

[0052] Zeolites may also be used as builders in the present invention. Several zeolites suitable for incorporation into the products of this disclosure are available to compounders, including the common zeolite 4A. Furthermore, MAP type zeolites, such as those taught in European Patent No. 384,070(B), are commercially available as Doucil A24, for example, by Ineos Silicas (UK), and are also acceptable for incorporation. MAP is defined as a zeolite P-type alkali metal aluminosilicate having a silicon-to-aluminum ratio not exceeding 1.33, preferably in the range of 0.90 to 1.33, more preferably in the range of 0.90 to 1.20.

[0053] Zeolite MAP with a silicon-to-aluminum ratio not exceeding 1.07, more preferably about 1.00, is particularly preferred. The particle size of the zeolite is not important. Zeolite A or zeolite MAP of any suitable particle size can be used. In any case, since zeolite is an insoluble substance, it is advantageous to minimize their levels in the composition of the present invention. For this reason, preferred formulations contain less than about 10% zeolite builder, while particularly preferred compositions contain less than about 5% zeolite.

[0054] When enzymes, particularly proteases, are used in liquid detergent formulations, it is often necessary to include an appropriate amount of enzyme stabilizer to temporarily inactivate them until they are used for washing. Examples of suitable enzyme stabilizers are well known to those skilled in the art and include, for example, borate and polyols such as propylene glycol. In addition to this effect, borate can further buffer the pH of detergent products over a wide range and thus provide excellent flexibility, making it particularly suitable for use as an enzyme stabilizer.

[0055] When borate-based enzyme-stabilized systems are selected with one or more cationic polymers, which consist at least partially of carbohydrate moieties, stability problems may arise if a suitable co-stabilizer is not used. This is thought to be a result of borate's natural affinity for hydroxyl groups, which can produce insoluble borate polymer complexes that precipitate from solution either over time or at low temperatures. This can usually be prevented by incorporating a co-stabilizer into the formulation, which is typically a diol or polyol, a sugar, or another molecule having a large number of hydroxyl groups. Sorbitol is particularly preferred for use as a co-stabilizer, and is used at a level of at least about 0.8 times the level of borate in the system, more preferably 1.0 times the level of borate in the system, and most preferably more than 1.43 times the level of borate in the system. Sorbitol is effective, inexpensive, biodegradable, and readily available on the market. Similar materials, including sugars such as glucose and sucrose, as well as other polyols such as propylene glycol, glycerol, mannitol, maltitol, and xylitol, should also be considered within the scope of the present invention.

[0056] To enhance the conditioning, softening, wrinkle-reducing, and protective effects of the compositions of the present invention, it is often desirable to include one or more fiber lubricants in the formulation. Such components are well known to those skilled in the art and are intended to reduce the coefficient of friction between fibers and yarns in the article being treated, both during and after the washing process. This effect can, in turn, improve the consumer's perception of softness, minimize wrinkle formation, and prevent damage to fibers during washing. For the purposes of this disclosure, “fiber lubricant” shall be considered a noncationic material intended to lubricate fibers for the purpose of reducing friction between fibers or yarns in an article containing fibers that provide one or more wrinkle-reducing, fabric conditioning, or protective effects.

[0057] Examples of suitable fiber lubricants include oily sugar derivatives, functionalized plant and animal oils, silicones, mineral oils, and natural and synthetic waxes.

[0058] Suitable oily sugar derivatives for use in the present invention are taught in International Publication No. 98 / 16538, which is incorporated herein by reference. These are particularly preferred as fiber lubricants due to their readily available and favorable environmental profile. When used in the compositions of the present invention, such materials are typically present at a level of about 1% to about 10% of the final composition. Another class of acceptable components 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 are identified as effective fiber lubricants. Suitable vegetable-derived triglyceride materials include hydrophilically modified triglyceride oils, e.g., sulfated, sulfonated, carboxylated, alkoxylated, esterified, sugar-modified, and amide-derived oils, tall oils and their derivatives. Suitable animal-derived triglyceride materials include hydrophilically modified fish oils, tallow, lard, and lanolin wax. A particularly preferred functionalized oil is sulfated castor oil, which is commercially available, for example, as Freedom SCO-75 from Noveon (Cleveland, Ohio).

[0059] Various levels of derivatization can be used, provided that the oil or wax derivative is sufficiently derivatized to be soluble or dispersible in the solvent used to provide a fiber lubrication effect during washing of fabrics with detergents containing the oil or wax derivative.

[0060] If the present invention includes a synthetically derived functionalized oil, this oil is preferably a silicone oil. More preferably, it is either a silicone polyether or an amino-functionalized silicone.

[0061] In many liquid and powder detergent compositions, hydrotropes are commonly added to alter the viscosity of the product, prevent liquid phase separation, and facilitate the dissolution of powders. Two types of hydrotropes are typically used in detergent formulations and are applicable to the present invention. The first of these is short-chain functionalized amphiphilic substances. Examples of short-chain amphiphilic substances include alkali metal salts of xylenesulfonic acid, cumenesulfonic acid, and octylsulfonic acid. Furthermore, organic solvents, as well as monohydric and polyhydric alcohols with a molecular weight of less than about 500, such as ethanol, isopropanol, acetone, propylene glycol, and glycerol, can also be used as hydrotropes.

[0062] To prevent re-soiling of fabrics during and after washing, one or more antifouling agents may be added to the product of the present invention. Depending on the formulation in use and the desired effect, many different types of antifouling agents are known to those skilled in the art. Antifouling agents useful in the context of the present invention are typically either anti-re-adhesion aids or antifouling finishes. Examples of anti-re-adhesion agents include antifouling polymers, such as those described in International Publication No. 99 / 03963, which are incorporated herein by reference.

[0063] Preferably, the carbohydrate portion in the monoester glycolipid is a disaccharide. Preferred disaccharides may be, for example, maltose, sucrose, lactose, cellobiose, trehalose, and isomaltose. Preferably, the disaccharide is derived from a polysaccharide such as starch, for example, by enzymatic cleavage. The inventors have found that, possibly due to steric hindrance, only a C6-alcohol reacts with the fatty acid when the carbohydrate is glucose, and either a C6-alcohol or a C6'-alcohol reacts with the fatty acid when the carbohydrate is maltose. In one or more embodiments, the monoester glycolipid or a mixture of monoester glycolipids contains a carbohydrate portion which is maltose.

[0064] In one or more embodiments, the carbohydrate portion in the monoester glycolipid is selected from the group consisting of maltose, cellobiose, trehalose, isomaltulose, lactulose, isomaltose, and mixtures thereof.

[0065] In one or more embodiments, the carbohydrate portion in the monoester glycolipid is selected from the group consisting of maltose, cellobiose, trehalose, and mixtures thereof.

[0066] In one or more embodiments, the monoester glycolipid or mixture of monoester glycolipids comprises a polysaccharide such as starch, with a disaccharide carbohydrate portion derived, for example, by enzymatic cleavage.

[0067] 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.

[0068] The performance of a surfactant depends on the balance between the hydrophilicity of the head group and the hydrophobicity of the tail group. In the case of monoester glycolipids, this corresponds to the hydrophilicity of the carbohydrate portion and the hydrophobicity of the hydrocarbon portion. In the case of disaccharides, the solubility in water, and therefore the hydrophilicity, can vary by up to an order of magnitude (as seen in the table below). This makes it difficult to predict whether surfactants made from these different disaccharides will exhibit similar properties and be suitable as surfactants in laundry detergent formulations. [Table 1]

[0069] In one or more embodiments, the monoester glycolipid comprises a lipid portion derived from diglycerides and / or triglycerides selected from sources consisting of sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, animal fat, lard, rice bran oil, coconut oil, linseed oil, palm oil, shea butter, shea butter oil, mango oil, kalahari melon seed oil, almond oil, poppy oil, plum kernel oil, grapeseed oil, apricot kernel oil, and mixtures thereof. The most common fatty acids present in many of the above oils are oleic acid, linoleic acid, stearic acid, and palmitic acid (as is evident from the table below), and the lipid portion is primarily one of these four fatty acids. [Table 2]

[0070] As used herein, the term “glyceride” (also known as acylglycerol) refers to monoglycerides, diglycerides, triglycerides, or combinations thereof. They are esters formed from glycerol and fatty acids. Glycerides in oils may contain multiple fatty acids, which may be saturated or unsaturated. As used herein, the term “triglyceride” refers to an ester derived from glycerol and three fatty acids. Triglycerides in this disclosure may be saturated or unsaturated. Similarly, the term “diglyceride” refers to an ester derived from glycerol and two fatty acids, and the term “monoglyceride” refers to an ester derived from glycerol and one fatty acid.

[0071] Preferably, the triglyceride source is selected from sources consisting of sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, animal fat, lard, rice bran oil, coconut oil, linseed oil, palm oil, shea butter, shea butter oil, mango oil, and mixtures thereof.

[0072] As used herein, the term “fatty acid” refers to molecules composed of carboxylic acids derived from triglycerides, having long, saturated or unsaturated aliphatic tails (chains). When not bound to other molecules, they are known as “free” fatty acids. Most naturally occurring fatty acids have chains of an even number of carbon atoms, from 4 to 28. Short-chain fatty acids (SCFAs) are fatty acids with an aliphatic tail of fewer than 6 carbon atoms. Medium-chain fatty acids (MCFAs) are fatty acids with an aliphatic tail of 6 to 12 carbon atoms and can form medium-chain triglycerides. Long-chain fatty acids (LCFAs) are fatty acids with an aliphatic tail of 13 to 21 carbon atoms. Very long-chain fatty acids (VLCFAs) are fatty acids with an aliphatic tail longer than 22 carbon atoms. For example, a fatty acid or its ester may contain at least 10, at least 12, at least 14, at least 16, at least 18, or at least 20 carbon atoms. In some specific examples, 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, and any of the listed values ​​may be the higher or lower endpoint, where appropriate. In other examples, glycerides may contain mixtures of fatty acids or their esters having different ranges of carbon atoms.

[0073] In a preferred embodiment, the monoester glycolipid comprises a lipid moiety having a chain length in the range of C6 to C26, which is saturated or unsaturated by 1 to 6 double bonds, preferably 1 to 3 double bonds, for example, 1 to 2 double bonds. More preferably, the chain length is in the range of C10 to C18. More preferably, the chain length is in the range of C16 to C18.

[0074] In one or more embodiments, the monoester glycolipid or mixture of monoester glycolipids comprises a carbohydrate portion which is maltose, and the monoester glycolipid comprises a lipid portion which is derived from diglycerides and / or triglycerides selected from a source of sunflower oil.

[0075] In one or more embodiments, a monoester glycolipid or a mixture of monoester glycolipids comprises a carbohydrate portion which is maltose, and the monoester glycolipid comprises a lipid portion which is saturated or unsaturated by 1 to 6 double bonds and has a chain length in the range of C6 to C26. More preferably, the chain length is in the range of C10 to C18. More preferably, the chain length is in the range of C16 to C18.

[0076] In one or more embodiments, the monoester glycolipid or mixture of monoester glycolipids comprises a carbohydrate portion which is maltose, and the monoester glycolipid comprises a lipid portion which is preferably derived from sunflower oil, derived from diglycerides and / or triglycerides selected from sources consisting of sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, animal fat, lard, rice bran oil, coconut oil, mango oil, kalahari melon seed oil, almond oil, poppy oil, plum kernel oil, grapeseed oil, apricot kernel oil, linseed oil, palm oil, shea butter, shea butter oil, and mixtures thereof.

[0077] A third aspect relates to a method for cleaning fibers and / or textile articles, the method being: - A step of providing a laundry detergent composition comprising a monoester glycolipid or a mixture of monoester glycolipids in a concentration for effectively washing fabrics / textiles under specified washing conditions. The steps of bringing one or more fibers and / or textile articles into contact with a laundry detergent composition at one or more points in the washing process, and The process includes the step of drying or mechanically tumble-drying the fibers and / or textile articles.

[0078] Another aspect of the present invention relates to a process for producing monoester glycolipids, wherein the process is: (i) Dispersing and / or solubilizing the carbohydrate in a polar organic solvent in a reaction vessel; (ii) Adding diglycerides and / or triglycerides to the reaction vessel to form a starting mixture; (iii) Dispersing the lipase in the starting mixture under stirring; (iv) Transesterification between the carbohydrate and the diglyceride and / or triglyceride at a temperature of 0 to 100°C to form a first liquid fraction comprising the polar organic solvent, monoester glycolipid, glycerol, and monoglyceride, diglyceride and / or triglyceride, and a first solid fraction comprising lipase and optionally unreacted carbohydrate; (v) the step of separating the first liquid fraction from the first solid fraction; and (vi) The step of separating monoester glycolipids from the first liquid fraction to form a second liquid fraction containing monoglycerides, diglycerides and / or triglycerides and glycerol.

[0079] This concept involves using lipase to catalyze transesterification between carbohydrates and diglycerides and / or triglycerides to form monoester glycolipids and glycerides with one less fatty acid attached (i.e., monoglycerides or diglycerides, respectively). Depending on the type of lipase, diglycerides (diacylglycerols) may serve as substrates for the new reaction with another carbohydrate molecule to form monoester glycolipids and monoglycerides. Again, depending on the lipase used, monoglycerides (monoacylglycerols) may serve as substrates for the new reaction with another carbohydrate molecule to form monoester glycolipids and glycerols. In this context, the term “transesterification” refers to a chemical reaction in which an alkoxy group of an ester compound, i.e., a diglyceride and / or triglyceride (and optionally a later-formed monoglyceride), is exchanged for another alkoxy group via the reaction of the ester with an alcohol, i.e., a carbohydrate, in the presence of a catalyst, i.e., a lipase.

[0080] Since each lipase exhibits different fatty acid specificity, it is important to select the appropriate lipase depending on the fatty acid species of the glyceride. When non-positional specificity is desired, i.e., when all fatty acids can be cleaved / transferred from the glyceride, a lipase with non-positional specificity is selected. Suitable examples include, for instance, Candida antarctica B lipase, lipase OF (derived from Candida rugosa), lipase G (derived from Penicillum camembertii), lipase AYS (derived from Candida rugosa), lipase PS (derived from Burkholderia cepacia), lipase AK (derived from Pseudomonas flourescens), lipase AS (derived from Aspergillus niger), and lipase M (derived from Mucor javanicus). When regiospecificity is desired, i.e., when only a portion of the fatty acid can be cleaved / transferred from the glyceride, a lipase with regiospecificity is selected. Appropriate examples of 1,3-position specificity include, for example, lipase F-AP15 (derived from Rhizopus oryzae), lipase newlase F3G (derived from Rhizopus niveus), lipase R (derived from Penicillum roqueforti), lipozyme RM-IM (derived from Rhizomucor miehei), lipozyme TL-IM (derived from Thermomyces lanuginosus), and pancreatic lipase (derived from porcine pancreas).

[0081] In one or more embodiments, the lipase is selective for the 1-position, 3-position, or both positions in the glyceride.

[0082] In one or more embodiments, the lipolytic enzymes selective to the 1st, 3rd, or both positions include: Chromobacterium viscosum, canine gastric lipase, canine pancreatic lipase, Fusarium solani cutinase lipase, guinea pig pancreatic lipase, human gastric lipase, Humicola lanuginosus lipase, human pancreatic lipase, lipoprotein lipase, Mucor miehei lipase, Pseudomonas aeruginosa lipase, Penicillium camemberti lipase, and Pseudomonas fluorescein. The lipases are selected from *Fluorescens* lipase, *Pseudomonas glumae* lipase, porcine pancreatic lipase, *Penicillium simplicissimum* lipase, *Rhizopus arrhizus* lipase, rabbit stomach lipase, *Fusarium heterosporum* lipase, *Candida rugosa* lipase, and their variants.

[0083] In one or more embodiments, the lipase is non-selective to the position in the glyceride.

[0084] In one or more embodiments, the process further includes the step (vii) of separating monoglycerides, diglycerides and / or triglycerides from a second liquid fraction.

[0085] Monoglycerides are used as emulsifiers in many foods, including whipped cream, baked goods, and ice cream.

[0086] In one or more embodiments, the lipase is selective for the 1st and 3rd positions in the glyceride, and the process further comprises the step (vii) of separating the formed monoglyceride from a second liquid fraction.

[0087] Diglycerides are commonly used as food additives to blend certain ingredients together, such as oils and water. Furthermore, both monoglycerides and diglycerides are recommended as foaming agents and shelf-life extenders in bakery margarine and shortening. They are also used as foaming agents in ice cream and imitation cream.

[0088] In one or more embodiments, a triglyceride is added to the reaction vessel, the lipase is selective for position 1 in the glyceride, and the process further comprises the step (vii) of separating the formed diglyceride from a second liquid fraction.

[0089] In one or more embodiments, a triglyceride is added to the reaction vessel, the lipase is selective for the 1,3 positions in the glyceride, and the process further comprises the step (vii) of separating the formed diglyceride from a second liquid fraction.

[0090] The lipolytic enzyme specificity described above (both saturated and unsaturated specificity, and specificity of 1, 3) is expected to increase at low conversion rates, decrease simultaneously with the depletion of preferred substrates, and increase simultaneously with the depletion of less preferred substrates. Therefore, it is preferable to carry out the reaction at a low conversion rate to ensure the highest possible specificity. In certain embodiments of the present invention, it is advantageous to maximize the utilization of all reaction products even at low transesterification conversion rates.

[0091] In one or more embodiments, the present invention relates to a process in which the conversion of monoester glycolipids to 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%.

[0092] In one or more embodiments, the present invention relates to a process in which the conversion of monoester glycolipids to monoglycerides or diglycerides is at least 40%, at least 45%, at least 50%, at least 55%, at least 60%, at least 65%, or at least 70%.

[0093] In one or more embodiments, the present invention relates to a process in which the lipase is selective for saturated fatty acids, and is preferably a lipase selected from Candida antarctica lipase A, Fusarium oxysporum lipase, and their variants.

[0094] A separation method for purifying monoglycerides or diglycerides from the first liquid fraction can 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 alcohol (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 and is well known in the art. The deodorizer can be operated at 0.15 mbar, 225°C, and a vapor flow rate of 0.20% to 0.25% w / w per hour. Other operating modes are known in the art; see, for example, "Introduction to Fats and Oil Technology," Eds O'Brien, Farr and Wan, AOCS Press, 2000, chapter 13.

[0095] Methods of distillation and evaporation are also known in the art. The oil evaporation unit is typically a steam distillation unit, also known as a deodorizer. In step (VIII), it is an embodiment to use distillation under high vacuum to minimize thermal damage. In certain embodiments of the present invention, it is preferable to use a system having multiple equilibrium stages to achieve good separation. Other preferred embodiments include a fall film molecular distiller operating at a pressure of 0.001 mmHg to 10 mmHg and a temperature of 140°C to 200°C, or a centrifugal molecular distiller that can operate at a pressure of about 0.001 mmHg to 10 mmHg and a temperature of 160°C to 240°C (both of these modes are described in detail in Batistella et al., Appl. Biotechn, vol. 98, 1149-1159, 2002). Direct or indirect heating may be used, and operation in batch and / or continuous operation is possible.

[0096] Transesterification may be carried out at a temperature in the range of 20 to 95°C, preferably in the range of 30 to 85°C, for example in the range of 40 to 75°C, for example in the range of 50 to 65°C, for example in the range of about 60°C, depending on the optimal conditions for lipase function.

[0097] Transesterification can preferably be carried out over a period ranging from several minutes, for example 5 minutes, to several hours, for example 120 hours, depending on the reaction time of the reactants used.

[0098] Preferred solvents used in transesterification reactions are tert-amyl alcohol, acetone, tert-butanol, 1-propanol, isopropanol, isobutanol, and isoamyl alcohol.

[0099] The resulting glycolipids can be purified by standard methods, such as extraction, filtration with mesoporous adsorbents or filters, affinity or adsorption-based chromatography using various solvents, distillation of any remaining volatile solvents, and centrifugation of precipitated products, by-products, or reactants.

[0100] Suitable solvents for chromatography include, for example, water, methanol, ethyl acetate, ethanol, pentane, hexane, heptane, acetone, methyl ethyl ketone, dichloromethane, tert-amyl alcohol, and 1-propanol.

[0101] The disclosed method for producing monoester glycolipids is illustrative but preferred. Other methods are also intended by the present invention.

[0102] Another aspect relates to monoester glycolipids produced by the process according to the present invention.

[0103] Another aspect relates to monoglycerides and / or diglycerides produced by a process according to the present invention.

[0104] It should be noted that embodiments and features described in one context of the present invention also apply to other aspects of the present invention.

[0105] example Example 1 - Production of monoester glycolipids A monosaccharide or disaccharide was added to a stirring 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 (compared to the mass of sugar). The reaction mixture was heated to 60°C and stirred for 120 hours. The product was detected by TLC analysis and subsequently purified by column chromatography by elution with DCM:MeOH.

[0106] Examples of solvents tested and used include tert-amyl alcohol, acetone, tert-butanol, 1-propanol, isopropanol, isobutanol, and isoamyl alcohol.

[0107] Examples of lipases tested and used include Candida antarctica B lipase, Lipozyme RM-IM (derived from Rhizomucor miehei), and Lipozyme TL-IM (derived from Thermomyces lanuginosus).

[0108] Monoester glycolipids are synthesized based on maltose, sucrose, cellobiose, trehalose, galactose, and glucose. Other reactants were 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 the carbohydrates.

[0109] This demonstrates that, as is generally known about carbohydrates, not all sugars behave the same way despite having similar or identical chemical compositions. For example, maltose, sucrose, and lactose all have the same chemical composition (C 12 H 22 O 11 Although it possesses these properties, it has been proven that synthesis was successful only with sucrose and maltose among these three.

[0110] Monoester glycolipids synthesized based on monosaccharides (glucose and galactose) were very poorly soluble in water and therefore could not be used in subsequent tests in the following examples.

[0111] Example 2 - Comparison of Laundry Detergent Compositions A series of four laundry detergent compositions were prepared, each containing only one component different from the others. Three different commercially available nonionic surfactants (#1, #3, #4) were selected for testing against the monoester glycolipid (#2, SBS1) according to the present invention.

[0112] SBS1 is a monoester glycolipid in which the carbohydrate portion is maltose and the lipid portion is oleic acid (6- and / or 6'-oleyl-maltose).

[0113] D-glucopyranose, oligomers, and decyloctyl glycosides can be purchased 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 group is also known as alkyl polyglucoside.

[0114] Secondary alcohols (C12-C14) ethoxylate 31EO can be purchased under the trade name Tergitol 15-S-30. Tergitol 15-S-30 is a nonionic surfactant commonly used in a variety of applications, including laundry detergents. Tergitol 15-S-30 is a mixture of C12-14 secondary alcohols ethoxylated with an average of 31 ethylene oxide (EO) units.

[0115] Decaethylene glycol monododecyl ether belongs to the class of nonionic surfactants and is often used in laundry detergent compositions. It is formed by ethoxylation of dodecyl alcohol with ethylene oxide, producing a molecule with 10 ethylene oxide units (hence "decaethylene"). This structure results in different surfactant properties. [Table 3]

[0116] Different detergents will be tested for their cleaning power, wettability, foaming ability, and emulsifying properties.

[0117] Cleaning power method The cleaning power was measured by contaminating a sample fabric with sunflower oil and then washing it with the formulation. A sample of fabric was cut to 7 x 7 cm. 10 mL of sunflower oil was diluted with 100 mL of dichloromethane. The sample was folded, immersed in the solution at room temperature for 5 minutes, unfolded, and then dried overnight. The sample was weighed before and after to determine the amount of accumulated oil. Washing was performed using 1000 mL of a washing solution prepared by diluting 50 mL of the detergent formulation with 1000 mL of deionized water (approximately 1% total surfactant). Four samples in one chamber were washed simultaneously in repeated cycles. The stirring speed was set to 200 rpm, and the washing time was 20 minutes at room temperature. Immediately after the washing cycle, the samples were rinsed with 1000 mL of deionized water for 10 minutes, even at room temperature. The washed samples were completely dried to determine the cleaning power. Detergent efficiency was given by the percentage of oil removed, with higher values ​​indicating better cleaning power. [Table 4]

[0118] Formulations containing monoester glycolipids (#2, SBS1) perform better on cotton fabrics than commercially available surfactant-containing formulations and exhibit comparable effectiveness on cotton / polyester mixtures.

[0119] foaming method Foaming ability and foaming stability are measured by mixing and determining the foam height at t=1 and t=30 minutes. For the test, 5 mL of the desired surfactant formulation was used in a 1:200 dilution (approximately 0.1% total surfactant) and the test was performed three times. This was added to a 15 mL centrifuge tube with a screw cap. Foaming was initiated by handshake of the centrifuge tube for 10 seconds and sedimentation for 50 seconds. Foaming ability was obtained by measuring the foam height up to time=1 minute. The sample was allowed to stand and the foam height was measured at time=30 minutes. Foam stability was determined by the ratio of the foam heights at time=1 minute and time=30 minutes. [Table 5]

[0120] Formulations containing monoester glycolipids (#2, SBS1) exhibit effects equivalent to those of commercially available formulations containing surfactants. Laundry detergents should preferably be relatively low-foaming. The compound used in formulation #1 is considered a low-foaming surfactant.

[0121] Emulsification index-E24 method The emulsification index (E24) was determined by mixing the surfactant formulation with oil and measuring the emulsion height to determine the formulation's ability to dissolve hydrocarbons. For the test, 5 mL of a 1:200 aqueous dilution of the surfactant formulation (approximately 0.1% total surfactant) and 5 mL of either paraffin oil (low viscosity), sunflower oil, olive oil, or frying oil were added to a 15 mL centrifuge tube. The test was performed three times. The formulation dilutions were mixed by handshake in the centrifuge tube for 10 seconds at room temperature and set to stand at room temperature. E24 was determined by the ratio of the emulsion height to the total volume height after 24 hours of mixing. The same procedure was used for palm oil (refined), except that solid palm oil was first heated to 40°C to melt it. After mixing, the sample was left to stand for 24 hours while maintaining a constant temperature of 35°C, and then E24 was measured as described above. [Table 6]

[0122] Formulations containing monoester glycolipids (#2, SBS1) function better or at an equivalent level to commercially available formulations containing surfactants.

[0123] Drapes Test - Wettability method Wettability is measured by the time it takes for a skein of cotton to sink in a surfactant solution. Good wettability helps water adhere to the surface of the fabric, remove air, and facilitate the removal of oil and dirt from the surface. A faster sinking time indicates better wettability. A 1:200 aqueous dilution of each surfactant formulation (approximately 0.1% total surfactant) was prepared for the test. 600 mL was placed in a graduated cylinder, and a 5 g skein of 100% cotton attached to a hook, along with a weight attached to a string, was placed inside. The time it took for the string to slacken was defined as the wetting time. The test was performed three times. [Table 7]

[0124] Formulations containing monoester glycolipids (#2, SBS1) function better than commercially available formulations containing surfactants.

[0125] Breakthrough test - Wettability method Wettability was measured by the time it took for a drop of the surfactant formulation to penetrate the oil disc. The sunflower oil used in the test was initially colored red to better visualize the breakthrough point. This was done by adding 0.05% w / w Oil Red O to the oil and stirring for 1 hour to ensure a uniform distribution. A small crystallization dish with a diameter of 70 mm was used for three tests. For each test, 35 g of water was poured into the dish. 2.5 g of colored oil was slowly added on top to form a thin disc. A 5 microliter drop of a 1:1 (approximately 10% total surfactant) diluted formulation was delicately deposited into the center of the oil disc using a finnpipette. Breakthrough time was measured from deposition to the breakthrough of the oil disc. [Table 8]

[0126] Formulations containing monoester glycolipids (#2, SBS1) exhibit the same efficacy as commercially available formulations containing surfactants.

[0127] Example 3 - Comparison of Laundry Detergent Compositions Using glycolipids, three more laundry detergent compositions were prepared. Again, only one component differed from the others, and compositions similar to those in Example 2 were selected. The three further monoester glycolipid compositions (#5 SBS2, #6 SBS3, and #7 SBS4) were tested together with #2 (SBS1) against commercially available nonionic surfactant formulations (#1, #3, and #4). SBS2 is a monoester glycolipid in which the carbohydrate portion is sucrose and the lipid portion is oleic acid (6- and / or 6'-oleyl-sucrose). SBS3 is a monoester glycolipid in which the carbohydrate portion is trehalose and the lipid portion is oleic acid (6- and / or 6'-oleyl-trehalose). SBS4 is a monoester glycolipid in which the carbohydrate portion is cellobiose and the lipid portion is oleic acid (6- and / or 6'-oleyl-cellobiose). [Table 9]

[0128] Emulsifying ability method Emulsifying ability was determined by mixing the surfactant formulation with oil and measuring the emulsion height to determine the formulation's ability to dissolve hydrocarbons. For the test, 1 mL of a 1:200 aqueous dilution of the surfactant formulation (approximately 0.1% total surfactant) and 1 mL of either sunflower oil, corn oil, or rapeseed oil were added to a 4 mL screw-cap vial. The test was performed three times. The formulation dilution was vortexed for 20 seconds and allowed to stand at room temperature. Emulsifying ability was determined by the ratio of the emulsion height to the total volume height after 10 minutes, 1 hour, 2 hours, and 3 hours after mixing. [Table 10]

[0129] [Table 11]

[0130] [Table 12]

[0131] The four formulations containing monoester glycolipids, #2(SBS1), #5(SBS2), #6(SBS3), and #7(SBS4), function with comparable efficacy to commercially available formulations containing surfactants. Furthermore, monoester glycolipids produced from maltose, trehalose, and cellobiose function as well as monoester glycolipids produced from sucrose, despite the significant differences in the solubility of the disaccharides themselves.

[0132] Example 4 - Effects of different amounts of nonionic surfactant A series of four laundry detergent compositions were prepared to test the effects of nonionic surfactants at different concentrations when replacing anionic surfactants. This was done by replacing a portion of the LAS (sodium dodecylbenzenesulfonate, anionic surfactant) present in the compositions described in Examples 1 and 2 with either a commercially available alkyl polyglycoside (APG) (Triton CG-110) or a monoester glycolipid according to the present invention (#2, SBS1). The increase in concentration was achieved by a 30% reduction / substitution of LAS (#8 and #9), while the others were achieved by approximately a 60% reduction / substitution of LAS (#10 and #11). [Table 13]

[0133] Different formulations are tested for their cleaning power, wettability, foaming ability, and emulsifying ability using the same procedure as described in Example 2. [Table 14]

[0134] With a 30% increase in nonionic surfactant, monoester glycolipid (SBS1) and commercially available APG (Triton CG-110) exhibit comparable cleaning efficacy. However, with a 60% increase in nonionic surfactant, the cleaning efficacy of monoester glycolipid (SBS1) formulations performs better than that of commercially available APG (Triton CG-110) for both 100% cotton and cotton / polyester mixtures. [Table 15]

[0135] For both 30% and 60% increases in nonionic surfactants, monoester glycolipids (SBS1) function better than commercially available nonionic APG (Triton CG-110), as laundry detergents should preferably be relatively low-foaming. [Table 16]

[0136] With a 30% increase in nonionic surfactant, monoester glycolipid (SBS1) and commercially available APG (Triton CG-110) exhibit comparable emulsifying capabilities. At a 60% increase, the emulsifying effect of monoester glycolipid (SBS1) formulations performs better than that of commercially available APG (Triton CG-110). [Table 17]

[0137] The wetting time indicates that commercially available APG (Triton CG-110) exhibits slightly better wettability for both formulations, and that nonionic surfactant concentrations increase by 30% and 60% compared to monoester glycolipid (SBS1).

[0138] Example 5 - Enzyme Activity Lipid-degrading activity was monitored using p-nitrophenyl butyrate, a chromogenic substrate. Briefly, different surfactant:lipase mixtures in 50 mM Tris 50 mM NaCl pH 8 buffer at an enzyme concentration of 10 nM were incubated at 25°C for 10 minutes before analysis to ensure a stable temperature. The substrate was then injected from a 15 mM stock solution to a final concentration of 0.12 mM, and the release of the chromogenic product was monitored by measuring the absorbance at 405 nm for several minutes using a Clariostar plate reader (BMG LABTECH, Ortenberg, Germany). The activity was then determined by linear regression as the slope resulting from a linear range and normalized to the activity of the lipase in the buffer. The experiment was performed three times. The enzyme used was lipase purified from the commercially available formulation Lipex® Evity® 200 L (Novozymes), manufactured for laundry detergents, using dialysis and ion exchange chromatography (to ensure only the interaction between the surfactant and the enzyme). Lipex® Evity® 200L is a mutant of the Thermomyces lanuginosa lipase family. The surfactants used are shown in the table below, and the results are shown in Figure 1. [Table 18]

[0139] The typical concentration of surfactants during washing is at least 200 mg / L. The data shows that enzymes lose activity in the presence of even small amounts of surfactant. Most commercially available surfactants tested yield 5–10% lipase activity above 200 mg / L. Triton APG yields 70% interpolated lipase activity at 200 mg / L, but lipase activity decreases rapidly at higher concentrations. Monoester glycolipid (SBS1) yields a remarkable increase in lipase activity above 100 mg / L, surpassing Triton APG at approximately 800 mg / L (interpolated value). This indicates that monoester glycolipid (SBS1) is a better choice for future laundry detergents for washing machines that utilize less water than current washing machines. Furthermore, since SBS1 yields a relative increase in lipase activity at higher concentrations, it suggests that SBS1 is milder on enzymes and likely to be compatible with other enzyme types such as proteases, amylases, and cellulases, which may be part of laundry detergent formulations.

Claims

1. The use of monoester glycolipids or mixtures of monoester glycolipids in laundry detergent compositions, The use of the monoester glycolipid or mixture of monoester glycolipids is characterized by comprising a 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, for example, from a polysaccharide such as starch obtained by enzymatic cleavage.

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

5. The use according to any one of claims 1 to 4, wherein the monoester glycolipid comprises a lipid portion derived from diglycerides and / or triglycerides selected from sources consisting of sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, animal fat, lard, rice bran oil, coconut oil, linseed oil, mango oil, kalahari melon seed oil, almond oil, poppy oil, plum kernel oil, grapeseed oil, apricot kernel oil, palm oil, shea butter, shea butter oil, and mixtures thereof.

6. The use according to any one of claims 1 to 4, wherein the monoester glycolipid comprises a lipid portion having a chain length in the range of C6 to C26, which is saturated or unsaturated by 1 to 6 double bonds such as oleic acid and / or linoleic acid and / or stearic acid and / or palmitic acid and / or palmiteradicic acid and / or palmitoleic acid.

7. The use according to any one of claims 1 to 4, wherein the monoester glycolipid comprises a lipid portion having a chain length in the range of C16 to C18, which is saturated or unsaturated by 1 to 6 double bonds such as oleic acid and / or linoleic acid and / or stearic acid and / or palmitic acid and / or palmitoleic acid.

8. A laundry detergent composition, It contains monoester glycolipids or a mixture of monoester glycolipids, A laundry detergent composition 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.

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 is lipase.

11. The laundry detergent composition according to claim 10, wherein the lipase is derived from a strain or variant of Thermomyces lanuxosus (TLL).

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

14. The laundry detergent composition according to any one of claims 8 to 13, wherein the monoester glycolipid comprises a lipid portion derived from diglycerides and / or triglycerides selected from a source consisting of sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, animal fat, lard, rice bran oil, coconut oil, mango oil, kalahari melon seed oil, almond oil, poppy oil, plum kernel oil, grapeseed oil, apricot kernel oil, linseed oil, palm oil, shea butter, shea butter oil, and mixtures thereof, preferably a lipid portion derived from sunflower oil.

15. The use according to any one of claims 8 to 13, wherein the monoester glycolipid comprises a lipid portion having a chain length in the range of C6 to C26, which is saturated or unsaturated by 1 to 6 double bonds such as oleic acid and / or linoleic acid and / or stearic acid and / or palmitic acid and / or palmiteradicic acid and / or palmitoleic acid.

16. The use according to any one of claims 8 to 13, wherein the monoester glycolipid comprises a lipid portion having a chain length in the range of C16 to C18, which is saturated or unsaturated by 1 to 6 double bonds such as oleic acid and / or linoleic acid and / or stearic acid and / or palmitic acid and / or palmitoleic acid.

17. A method for washing fibers and / or textile articles, - A step of providing a laundry detergent composition comprising a monoester glycolipid or a mixture of monoester glycolipids at a concentration for effectively washing fabrics / textiles under predetermined washing conditions. - A step of bringing one or more fibers and / or textile articles into contact with the laundry detergent composition at one or more points in the washing process, and - The process includes the step of drying the fibers and / or textile articles, or mechanically tumble-drying them. The method is 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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