EP4466333A1

EP4466333A1 - Use of mono-ester glycolipids in laundry detergents

Info

Publication number: EP4466333A1
Application number: EP24700361.9A
Authority: EP
Inventors: Kasper Telespher Olesen FALKENBERG; Daniel Lind JENSEN; Nicklas Højbro NØRGAARD
Original assignee: Norfalk Aps
Current assignee: Norfalk Aps
Priority date: 2023-03-09
Filing date: 2024-01-02
Publication date: 2024-11-27

Abstract

The present invention relates to the use of a mono-ester glycolipid or a mixture of mono-ester glycolipids in a laundry detergent composition. The mono-ester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety is selected from the group consisting of maltose, cellobiose, trehalose, isomaltulose, lactulose, isomaltose, and mixtures thereof.

Description

Use of mono-ester glycolipids in laundry detergents

Technical field of the invention

The present invention relates to laundry detergents.

Background of the invention

A laundry detergent is a composition that is used during the washing process of textile/laundry to remove unwanted substances therefrom. One of the most important group of compounds in a laundry detergent is surfactants, also called surface-active agents. A surfactant comprises a hydrophilic part, and a hydrophobic part, which makes it suitable to diffuse in water and get adsorbed at interfaces between water and unwanted substances on the textile. A bit simplified, here the surfactant molecules arrange and roll up around the unwanted substance and thereby releases it from the textile to form micelles with the unwanted substance within the micelles.

By varying either the hydrophilic part and/or the hydrophobic part, the properties, such as wetting ability, foaming ability, and dispersive ability, may be adjusted. Thereby, surfactants differ in their ability to remove certain types of unwanted substances, in their effectiveness on different types of textiles, and in their response to water hardness.

Currently used surfactants are shown to be very effective. However, consumer demands for new milder and "greener" laundry detergents mean that this area needs to be addressed again.

Summary of the invention

Thus, an object of the present invention is to provide a greener alternative to the currently used laundry detergents.

The inventors of the present invention have found use of a new subtype of non-ionic surfactants, mono-ester glycolipids, that is a greener alternative to conventional non-ionic surfactants for laundry detergents.

The inventors of the present invention have also found a process for producing mono-ester glycolipids from renewable sources, 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 mono-ester glycolipids are biodegradable. A part of the by-products (mono- and diglycerides) may even be separated as valuable food ingredients or food additives.

Thus, a first aspect relates to the use of a mono-ester glycolipid or a mixture of monoester glycolipids in a laundry detergent composition.

A second aspect relates to a laundry detergent composition comprising a mono-ester glycolipid or a mixture of mono-ester glycolipids.

A third aspect relates to a method for cleaning textiles and/or textile articles comprising the steps of:

- providing a laundry detergent composition comprising a mono-ester glycolipid or a mixture of mono-ester glycolipids, in a concentration to effectively clean fabrics/textile articles under predetermined laundering conditions;

- contacting one or more textiles and/or textile articles with the laundry detergent composition at one or more points during a laundering process; and

- allowing the textiles and/or textile articles to dry, or mechanically tumble-drying them.

The present invention will now be described in more detail in the following.

Detailed description of the invention

Glycolipids are amphoteric, anionic, cationic, or non-ionic molecules that comprise a hydrophilic carbohydrate moiety and one or more fatty acids as lipophilic moiety. Monoester glycolipids have a single fatty acid as the lipophilic moiety. The inventors of the present invention have also found that mono-ester glycolipids have comparable, and sometimes better, properties than some conventional non-ionic surfactants that are produced from petrochemicals and palm oil (see the experimental section for a selection of results).

A first aspect relates to the use of a mono-ester glycolipid or a mixture of mono-ester glycolipids in a laundry detergent composition.

The inventors of the present invention have found a process for producing mono-ester glycolipids from renewable sources. The laundry detergent composition of the present invention can take any of a number of forms. It can take the form of a dilutable laundry detergent, a surfactant-structured liquid, a granular, spray-dried or dry-blended powder, a tablet, a paste, a moulded solid, or any other laundry detergent form known to those skilled in the art.

A "dilutable laundry detergent" composition is defined, for the purposes of this disclosure, as a product intended to be used by being diluted with water by a ratio of more than 100 : 1, to produce a liquid suitable for cleaning textiles. Water soluble sheets or sachets, such as those described in U.S. Pat. Appl. No. 20020187909, are also envisaged as a potential form of this invention. These may be sold under a variety of names, and for a number of purposes.

Method of Use

The following details a method for cleaning textiles and/or textile articles comprising the steps, in no particular order of: i. providing a laundry detergent composition comprising a mono-ester glycolipid or a mixture of mono-ester glycolipids, in a concentration to effectively clean fabrics and/or textile articles under predetermined laundering conditions;

II. contacting one or more textiles and/or textile articles with the laundry detergent composition at one or more points during a laundering process; and ill. allowing the textiles and/or textile articles to dry or mechanically tumble-drying them.

Amounts of the laundry detergent composition used will generally range between about 10 g and about 300 g total product per 3 kg of textile articles, depending on the particular embodiment chosen and other factors, such as consumer preferences, that influence product use behaviour.

A consumer that would use the present invention could also be specifically instructed to contact the textile articles, such as clothes, with the inventive composition with the purpose of simultaneously cleaning and softening the said textile articles. This approach would be recommended when the composition takes the form of a softening detergent to be dosed at the beginning of the wash cycle.

In addition to the above-mentioned mono-ester glycolipid, the formulator may include one or more optional ingredients in the laundry detergent composition. While it is not necessary for these elements to be present in order to practice this invention, the use of such materials is often very helpful in rendering the formulation of the laundry detergent composition acceptable for consumer use. Examples of optional components include, but are not limited to: anionic surfactants, nonionic surfactants, amphoteric and zwitterionic surfactants, cationic surfactants, hydrotropes, fluorescent whitening agents, photobleaches, fiber lubricants, reducing agents, enzymes, enzyme stabilizing agents, powder finishing agents, defoamers, builders, bleaches, bleach catalysts, soil release agents, anti-redeposition agents, dye transfer inhibitors, buffers, colorants, fragrances, pro-fragrances, rheology modifiers, anti-ashing polymers, preservatives, insect repellents, soil repellents, water-resistance agents, suspending agents, aesthetic agents, structuring agents, sanitizers, solvents, fabric finishing agents, dye fixatives, wrinkle-reducing agents, fabric conditioning agents, and deodorizers.

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

- one or more enzymes.

The laundry detergent composition may further comprise one or more enzymes, which provide cleaning performance and/or fabric care benefits. The enzymes may include cellulases, hemicellulases, peroxidases, proteases, gluco-amylases, amylases, lipases, cutinases, pectinases, xylanases, mannanases, pectate lyases, reductases, oxidases, phenoloxidases, lipoxygenases, ligninases, pullulanases, tannases, pentosanases, malanases, - glucanases, arabinosidases or mixtures thereof.

A preferred combination is a laundry detergent composition having a mixture of conventional applicable enzymes like protease, amylase, lipase, cutinase, and/or cellulase in conjunction with the lipolytic enzyme variant D96L at a level of from 50 LU to 8500 LU per liter of wash solution.

A preferred lipase is selected from the Thermomyces lanuginosa lipase family. The Thermomyces lanuginosa lipase family refers to a group of lipase enzymes predominantly derived from the thermophilic fungus Thermomyces lanuginosa. These enzymes are known for their ability to break down lipids (fats) and have several unique characteristics, such as thermal stability, and substrate specificity.

Suitable cellulases include both bacterial and fungal cellulase. Preferably, they will have a pH optimum of between 5 and 9.5. Suitable cellulases are disclosed in U.S. Pat. No. 4,435,307, which discloses fungal cellulase produced from Humicola insolens. Suitable cellulases are also disclosed in GB-A-2075028; GB-A-2095275 and DE-OS- 2247832. Examples of such cellulases are cellulases produced by a strain of Humicola insolens (Humicola grisea var. thermoidea), particularly the Humicola strain DSM 1800. Other suitable cellulases are cellulases originated from Humicola insolens having a molecular weight of about 50,000, an isoelectric point of 5.5 and containing at least 415 amino acid units. Especially suitable cellulases are the cellulases having color care benefits. Examples of such cellulases are cellulases described in EP Appl. No.91202879.2. Preferred commercially available cellulase enzymes include those sold under the tradenames Celluclean®, Celluclean Classic®, Whitezyme® by Novozymes A/S, those sold under the tradenames Revitalenz® by IFF, and those sold under the tradenames Biotouch FLX® by AB Enzymes.

Peroxidase enzymes are used in combination with oxygen sources, e.g., percarbonate, perborate, persulfate, hydrogen peroxide, and the like. They are used for "solution bleaching", i.e., to prevent transfer of dyes or pigments removed from substrates during wash operations to other substrates in the wash solution. Peroxidase enzymes are known in the art, and include, for example, horseradish peroxidase, ligninase, and haloperoxidases such as chloro- and bromoperoxidase. Peroxidase-containing detergent compositions are disclosed, for example, in PCT Int. Appl. WO 89/099813 and in EP Appl. No.91202882.6.

The cellulases and/or peroxidases are normally incorporated in the laundry detergent composition at levels from 0.0001% to 2% of active enzyme by weight of the laundry detergent composition.

Preferred commercially available protease enzymes include those sold under the tradenames Liquanase®, Progress®, Blaze®, Alcalase®, Savinase®, Primase®, Durazym®, and Esperase® by Novozymes A/S, those sold under the tradename Maxatase®, Maxacai® and Maxapem® by Gist-Brocades, those sold by Genencor International, those sold under the tradename Opticlean® and Optimase® by Solvay Enzymes, those sold under the tradename Preferenz P® and Excellenz P® by IFF, and those sold under the trade names BIOTOUCH® ROC 250 LCO by AB Enzymes. Other proteases are described in U.S. Pat. No.5, 679, 630 can be included in the detergent compositions.

Protease enzyme may be incorporated into the detergent compositions at a level of from about 0.0001% to about 2% active enzyme by weight of the composition.

A preferred protease here referred to as "Protease D" is a carbonyl hydrolase variant having an amino acid sequence not found in nature, which is derived from a precursor carbonyl hydrolase by substituting a different amino acid for the amino acid residue at a position in the carbonyl hydrolase equivalent to position +76, preferably also in combination with 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 according to the numbering of Bacillus amyloliquefaciens subtilisin, as described in U.S. Pat. No. 5,679,630, the teachings of which are incorporated herein by reference. Highly preferred enzymes that can be included in the detergent compositions include lipases. It has been found that the cleaning performance on greasy soils is synergistically improved by using lipases. Lipases are enzymes that catalyze hydrolysis of fats and oils to fatty acids and glycerol, monoglycerides, and/or diglycerides. Suitable lipases for use herein include those of animal, plant, fungal, and microbiological origin. Suitable lipase enzymes can be found in cambium, bark, plant roots, and in the seeds of fruit, oil palm, lettuce, rice, bran, barley and malt, wheat, oats and oat flour, cotton tung kernels, corn, millet, coconuts, walnuts, fusarium, cannabis and cucurbit. In addition to naturally occurring lipases, chemically modified or protein engineered mutants can be used.

Suitable lipases include lipases from microorganisms of the Humicola group (also called Thermomyces), e.g., from H. lanuginosa (T. lanuginosus) as described, e.g., in EP 258 068 and EP 305 216, or from H. insolens (see, e.g., PCT Internat. Appl. WO 96/13580);

Pseudomonas lipases, e.g., from P. alcaligenes or P. pseudoalcaligenes (see, e.g., EP 218272), P. cepacia (see, e.g., EP 331376), P. stutzeri (see, e.g., British Pat. No. 1,372,034), P. fluorescens, Pseudomonas sp. strain SD 705 (see, e.g., PCT Internat. Appls. WO 95/06720 and WO 96/27002), or P. wisconsinensis (see, e.g., PCT Internat. Appl. WO 96/12012); or Bacillus lipases, e.g., from B. subtilis, B. stearothermophilus or B. pumilus (see, e.g., PCT Internat. Appl. WO 91/16422).

Lipase variants can be used, such as those described in U.S. Pat. Nos. 8,187,854; 7,396,657; and 6,156,552, the teachings of which are incorporated herein by reference. Additional lipase variants are described in PCT Internat. Appls. 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, and in EP 0 407 225 and EP 0260105.

Suitable lipases include those sold under the tradenames LipexTM, LipolexTM, LipocleanTM, LipolaseTM, Lipolase UltraTM, LipopanTM, Lipopan XtraTM, LypozymeTM, PalataseTM, ResinaseTM, NovozymTM 435, and LipoprimeTM (all from Novozymes). Other suitable lipases are available as Lipase P AmanoTM (Amano Pharmaceutical). Further suitable lipases are lipases, such as Ml LipaseTM and LipomaxTM (DSM) , LumafastTM (Danisco), and Preferenz L (IFF). Preferred lipases include the D96L lipolytic enzyme variant of the native lipase derived from Humicola lanuginosa as described in U.S. Pat. No. 6,017,871. Preferably, the Humicola lanuginosa strain DSM 4106 is used.

The lipase can be used at any suitable level. Generally, the lipase is present in the laundry detergent composition in an amount of 10 to 20000 LU/g of the detergent composition, or even 100 to 10000 LU/g. The LU unit for lipase activity is defined in WO99/42566. The lipase dosage in the wash solution is typically from 0.01 to 5 mg/L active lipase protein, more typically 0.1 to 2 mg/L. As a weight percentage, the lipase can be used in the detergent at 0.00001 to 2 wt.%, usually 0.0001 to 1 wt.%, or even 0.001 to 0.5 wt.%. The lipase may be incorporated into the detergent in any convenient form, e.g., nondusting granules, stabilized liquids, or protected (e.g., coated) particles.

For more examples of suitable lipases useful herein, see U.S. Pat. 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. Pat. Appl. Publ. No. 2011/0212877, the teachings of which are incorporated herein by reference.

Amylases (a and/or P) can be included for removal of carbohydrate-based stains. Suitable amylases are Termamyl® (Novozymes), Fungamyl® (Novozymes), BAN® amylases (Novozymes), Stainzyme Plus® (Novozymes), Amplify® (Novozymes), Achieve® (Novozymes), Preferenz S® (IFF), and Excellenz S® (IFF).

The above-mentioned enzymes may be of any suitable origin, such as vegetable, animal, bacterial, fungal and/or yeast origin. See U.S. Pat. No. 5,929,022, the teachings of which are incorporated herein by reference, from which much of the preceding discussion comes. Preferred compositions optionally contain a combination of enzymes or a single enzyme, with the amount of each enzyme commonly ranging from 0.0001% to 2%.

Other enzymes and materials used with enzymes are described in PCT Int. Appl. No. WO99/05242, which is incorporated here by reference.

Builders are often added to fabric cleaning compositions to complex and remove alkaline earth metal ions, which can interfere with the cleaning performance of a detergent by combining with anionic surfactants and removing them from the wash liquor. The preferred compositions of this invention, especially when used as a combination detergent/softener, contain builders.

Soluble builders, such as alkali metal carbonates and alkali metal citrates, are particularly preferred, especially for the liquid embodiment of this invention. Other builders, as further detailed below, may also be used, however. Often a mixture of builders, chosen from those described below and others known to those skilled in the art, will be used.

Alkali and alkaline earth metal carbonates, such as those detailed in German patent application 2,321,001, published Nov. 15, 1973, are suitable for use as builders in the compositions of this invention. They may be supplied and used either in anhydrous form or including bound water. Particularly useful is sodium carbonate, or soda ash, which both is readily available on the commercial market and has an excellent environmental profile. The sodium carbonate used in this invention may either be natural or synthetic, and, depending on the needs of the formula, may be used in either dense or light form. Natural soda ash is generally mined as trona and further refined to a degree specified by the needs of the product it is used in. Synthetic ash, on the other hand, is usually produced via the Solvay process or as a coproduct of other manufacturing operations, such as the synthesis of caprolactam. It is sometimes further useful to include a small amount of calcium carbonate in the builder formulation, to seed crystal formation and increase building efficacy.

Organic detergent builders can also be used as nonphosphate builders in the present invention. Examples of organic builders include alkali metal citrates, succinates, malonates, fatty acid sulfonates, fatty acid carboxylates, nitrilotriacetates, oxydisuccinates, alkyl and alkenyl disuccinates, oxydiacetates, carboxy methyloxy succinates, ethylenediamine tetraacetates, tartrate monosuccinates, tartrate disuccinates, tartrate monoacetates, tartrate diacetates, oxidized starches, oxidized heteropolymeric polysaccharides, polyhydroxysulfonates, polycarboxylates such as polyacrylates, polymaleates, polyacetates, polyhydroxyacrylates, polyacrylate/polymaleate and polyacrylate/polymethacrylate copolymers, acrylate/maleate/vinyl alcohol terpolymers, aminopolycarboxylates and polyacetal carboxylates, and polyaspartates and mixtures thereof. Such carboxylates are described in U.S. Pat. Nos. 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 especially preferred nonphosphate builders.

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

Phosphates are, however, often difficult to formulate, especially into liquid products, and have been identified as potential agents that may contribute to the eutrophication of lakes and other waterways. As such, the preferred compositions of this invention comprise phosphates at a level of less than about 10% by weight, more preferably less than about 5% by weight. The most preferred compositions of this invention are formulated to be substantially free of phosphate builders.

Zeolites may also be used as builders in the present invention. A number of zeolites suitable for incorporation into the products of this disclosure are available to the formulator, including the common zeolite 4A. In addition, zeolites of the MAP variety, such as those taught in European Patent Application EP 384,070B, which are sold commercially by, for example, Ineos Silicas (UK), as Doucil A24, are also acceptable for incorporation. MAP is defined as an alkali metal aluminosilicate of zeolite P type having a silicon to aluminium ratio not exceeding 1.33, preferably within the range of from 0.90 to 1.33, more preferably within the range of from 0.90 to 1.20.

Especially preferred is zeolite MAP having a silicon to aluminium ratio not exceeding 1.07, more preferably about 1.00. The particle size of the zeolite is not critical. Zeolite A or zeolite MAP of any suitable particle size may be used. In any event, as zeolites are insoluble matter, it is advantageous to minimize their level in the compositions of this invention. As such, the preferred formulations contain less than about 10% of zeolite builder, while especially preferred compositions compress less than about 5% zeolite.

When enzymes, and especially proteases are used in liquid detergent formulations, it is often necessary to include a suitable quantity of enzyme stabilizer to temporarily deactivate it until it is used in the wash. Examples of suitable enzyme stabilizers are well- known to those skilled in the art, and include, for example, borates and polyols such as propylene glycol. Borates are especially suitable for use as enzyme stabilizers because in addition to this benefit, they can further buffer the pH of the detergent product over a wide range, thus providing excellent flexibility.

If a borate-based enzyme stabilization system is chosen, along with one or more cationic polymers that are at least partially comprised of carbohydrate moieties, stability problems can result if suitable co-stabilizers are not used. It is believed that this is the result of borates' natural affinity for hydroxyl groups, which can create an insoluble borate-polymer complex that precipitates from solution either over time or at cold temperatures. Incorporating into the formulation a co-stabilizer, which is normally a diol or polyol, sugar or other molecule with a large number of hydroxyl groups, can ordinarily prevent this. Especially preferred for use as a co-stabilizer is sorbitol, used at a level that is 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, and other polyols such as propylene glycol, glycerol, mannitol, maltitol and xylitol, should also be considered within the scope of this invention.

In order to enhance the conditioning, softening, wrinkle-reduction and protective effects of the compositions of this invention, it is often desirable to include one or more fiber lubricants in the formulation. Such ingredients are well known to those skilled in the art and are intended to reduce the coefficient of friction between the fibers and yarns in articles being treated, both during and after the wash process. This effect can in turn improve the consumer's perception of softness, minimize the formation of wrinkles, and prevent damage to textiles during the wash. For the purposes of this disclosure, "fiber lubricants" shall be considered non-cationic materials intended to lubricate fibers for the purpose of reducing the friction between fibers or yarns in an article comprising textiles which provide one or more wrinkle-reduction, fabric conditioning or protective benefit. Examples of suitable fiber lubricants include oily sugar derivatives, functionalized plant and animal-derived oils, silicones, mineral oils, natural and synthetic waxes, and the like. Oily sugar derivatives suitable for use in this invention are taught in WO 98/16538, which is incorporated herein by reference. These are especially preferred as fiber lubricants, due to their ready availability and favorable environmental profile. When used in the compositions of this invention, such materials are typically present at a level between about 1% and about 10% of the finished composition. Another class of acceptable ingredients includes hydrophilically modified plant and animal oils and synthetic triglycerides. Suitable and preferred hydrophilically modified plant, animal, and synthetic triglyceride oils and waxes have been identified as effective fiber lubricants. Such suitable plant derived triglyceride materials include hydrophilically modified triglyceride oils, e.g., sulfated, sulfonated, carboxylated, alkoxylated, esterified, saccharide modified, and amide derivatized oils, tall oils and derivatives thereof, and the like. Suitable animal derived triglyceride materials include hydrophilically modified fish oil, tallow, lard, and lanolin wax, and the like. An especially preferred functionalized oil is sulfated castor oil, which is sold commercially as, for example, Freedom SCO-75, available from Noveon (Cleveland, Ohio). Various levels of derivatization may be used provided that the derivatization level is sufficient for the oil or wax derivatives to become soluble or dispersible in the solvent it is used in so as to exert a fiber lubrication effect during laundering of fabrics with a detergent containing the oil or wax derivative.

If this invention includes a functionalized oil of synthetic origin, preferably this oil is a silicone oil. More preferably, it is either a silicone poly ether or amino-functional silicone.

In many liquid- and powdered detergent compositions, it is customary to add a hydrotrope to modify product viscosity and prevent phase separation in liquids, and ease dissolution in powders. Two types of hydrotropes are typically used in detergent formulations and are applicable to this invention. The first of these are short-chain functionalized amphiphiles. Examples of short-chain amphiphiles include the alkali metal salts of xylenesulfonic acid, cumenesulfonic acid and octyl sulfonic acid, and the like. In addition, organic solvents, and monohydric and polyhydric alcohols with a molecular weight of less than about 500, such as, for example, ethanol, isoporopanol, acetone, propylene glycol and glycerol, may also be used as hydrotropes.

In order to prevent the resoiling of fabrics during and after the wash, one or more soil release agents may also be added to the products of this invention. Many different types of soil release agents are known to those skilled in the art, depending on the formulation in use and the desired benefit. The soil release agents useful in the context of this invention are typically either antiredeposition aids or stain-repelling finishes. Examples of antiredeposition agents include soil release polymers, such as those described in WO99/03963, which is incorporated herein by reference.

Preferably, the carbohydrate moiety in the mono-ester glycolipid is a disaccharide.

Preferred disaccharides may e.g., be maltose, sucrose, lactose, cellobiose, trehalose, and isomaltose. Preferably, the disaccharide is derived from polysaccharides, such as starch, e.g., by enzymatic cleavage. The inventors of the present invention have found, probably due to steric hindrance, that it is only the C6-alcohol that reacts with the fatty acid when the carbohydrate is glucose, and either the C6-alcohol or the C6'-alcohol that reacts with the fatty acid when the carbohydrate is maltose. In one or more embodiments, the monoester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety being maltose.

In one or more embodiments, the carbohydrate moiety in the mono-ester glycolipid is selected from the group consisting of: maltose, cellobiose, trehalose, isomaltulose, lactulose, isomaltose, and mixtures thereof.

In one or more embodiments, the carbohydrate moiety in the mono-ester glycolipid is selected from the group consisting of: maltose, cellobiose, trehalose, and mixtures thereof.

In one or more embodiments, the mono-ester glycolipid or mixture of mono-ester glycolipids comprises a disaccharide carbohydrate moiety derived from polysaccharides, such as starch, e.g., by enzymatic cleavage.

In one or more embodiments, the mono-ester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety selected from the group consisting of maltose, cellobiose, trehalose, isomaltulose, lactulose, and isomaltose.

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 mono-ester glycolipids, this corresponds to the hydrophilicity of the carbohydrate moiety and the hydrophobicity of the hydrocarbon moiety. In the case of disaccharides, the solubility in water, and therefore hydrophilicity, varies by up to an order of magnitude (as seen in table below). This makes it non-trivial to predict whether the surfactants made from these different disaccharides would exhibit similar properties and be suitable as surfactants in laundry detergent formulations.

In one or more embodiments, the mono-ester glycolipid comprises a lipid moiety derived from a diglyceride and/or triglyceride selected from a source consisting of: sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, tallow, lard, rice bran oil, coconut oil, linseed oil, palm oil, shea butter, shea butter oil, mango oil, Kalahari melon seed oil, almond oil, poppy seed 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 evident from the table below), why the lipid moiety will predominately be one of these four fatty acids.

The term "glyceride" (also known as acylglycerol) as used herein refers to a monoglyceride, diglyceride, triglyceride, or combinations thereof. They are esters formed from glycerol and fatty acids. The glyceride in the oil can comprise a plurality of fatty acids saturated, unsaturated. The term "triglyceride" as used herein refers to an ester derived from glycerol and three fatty acids. The triglycerides of the present 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.

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

The term "fatty acid" as used herein refers to a molecule that is derived from a triglyceride and is comprised of a carboxylic acid with a long aliphatic tail (chain) which is either saturated or unsaturated. When not attached to other molecules, they are known as "free" fatty acids. Most naturally occurring fatty acids have a chain of an even number of carbon atoms, from 4 to 28. Short chain fatty acids (SCFA) are fatty acids with aliphatic tails of fewer than six carbons. Medium chain fatty acids (MCFA) are fatty acids with aliphatic tails of 6-12 carbons, which can form medium chain triglycerides. Long chain fatty acids (LCFA) are fatty acids with aliphatic tails 13 to 21 carbons. Very long chain fatty acids (VLCFA) are fatty acids with aliphatic tails longer than 22 carbons. In one example, the fatty acid or the ester thereof can comprise 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, the fatty acid or the ester thereof can contain 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 7 , 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, or 45 carbon atoms, where any of the stated values can form an upper or lower endpoint when appropriate. In other examples, the glyceride can comprise a mixture of fatty acids or the esters thereof having different ranges of carbon atoms.

In a preferred embodiment, the mono-ester glycolipid comprises a lipid moiety having a chain length within the range of C6-C26, saturated, or unsaturated with 1-6 double bonds, preferably 1-3 double bonds, such as 1-2 double bonds. More preferably, the chain length is within the range of C10-C18. More preferably the chain length is within the range of C16-C18.

In one or more embodiments, the mono-ester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety being maltose, and wherein said mono-ester glycolipid comprises a lipid moiety derived from a diglyceride and/or triglyceride selected from a source of sunflower oil.

In one or more embodiments, the mono-ester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety being maltose, and wherein said mono-ester glycolipid comprises a lipid moiety having a chain length within the range of C6-C26, saturated, or unsaturated with 1-6 double bonds. More preferably, the chain length is within the range of C10-C18. More preferably the chain length is within the range of C16- C18.

In one or more embodiments, the mono-ester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety being maltose, and wherein said mono-ester glycolipid comprises a lipid moiety derived from a diglyceride and/or triglyceride selected from a source consisting of: sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, tallow, lard, rice bran oil, coconut oil, mango oil, Kalahari melon seed oil, almond oil, poppy seed oil, plum kernel oil, grapeseed oil, apricot kernel oil, linseed oil, palm oil, shea butter, shea butter oil, and mixtures thereof, preferably derived from sunflower oil.

Another aspect of the present invention relates to a process for producing mono-ester glycolipids, the process comprising the steps of:

(i) dispersing and/or solubilizing a carbohydrate in a polar organic solvent in a reaction vessel;

(ii) adding a diglyceride and/or triglyceride to said reaction vessel to form a starting mixture;

(iii) dispersing a lipase in said starting mixture under stirring;

(iv) performing a transesterification between said carbohydrate and said diglyceride and/or triglyceride at a temperature between 0-100 degrees Celsius to form a first liquid fraction comprising said polar organic solvent, mono-ester glycolipid, glycerol and mono-, di- and/or triglyceride, and a first solid fraction comprising lipase and optionally unreacted carbohydrate;

(v) separating the first liquid fraction from the first solid fraction; and

(vi) separating the mono-ester glycolipid from the first liquid fraction to form a second liquid fraction comprising mono-, di- and/or triglyceride and glycerol.

The concept is to use a lipase to catalyse a transesterification between a carbohydrate and a diglyceride and/or triglyceride to form a mono-ester glycolipid and a glyceride with one less fatty acid bound thereto (i.e., a monoglyceride or a diglyceride, respectively). Depending on the type of lipase, the diglyceride (diacylglycerol) may serve as a substrate for a new reaction with another carbohydrate molecule to form a mono-ester glycolipid and a monoglyceride. Again, depending on the used lipase, the monoglyceride (monoacylglycerol) may serve as a substrate for a new reaction with another carbohydrate molecule to form a mono-ester glycolipid and glycerol. In the present context, the term "transesterification" designates the chemical reaction in which the alkoxy group of an ester compound, i.e., the diglyceride and/or triglyceride (and optionally a later formed monoglyceride), is exchanged with another alkoxy group via the reaction of said ester with an alcohol, i.e., the carbohydrate, in presence of a catalyst, i.e., the lipase.

As each lipase shows different fatty acid specificity, it is important to select an appropriate lipase according to the fatty acid species of the glyceride. If non-regio specificity is wanted, i.e., all fatty acids may be cleaved/transferred from the glyceride, a lipase with non-regio specificity is selected. Suitable examples may e.g., be Candida antarctica B lipase, Lipase OF (origin from Candida rugosa), Lipase G (origin from Penicillum camembertii), Lipase AYS (origin from Candida rugosa), Lipase PS (origin from Burkholderia cepacia), Lipase AK (origin from Pseudomonas flourescens), Lipase AS (origin from Aspergillus niger), and Lipase M (origin from Mucor javanicus). If regio specificity is wanted, i.e., only some of the fatty acids may be cleaved/transferred from the glyceride, a lipase with regio specificity is selected. Suitable examples for 1,3-regio specificity may e.g., be Lipase F-AP15 (origin from Rhizopus oryzae), Lipase Newlase F3G (origin from Rhizopus niveus), Lipase R (origin from Penicillum roqueforti), Lipozyme RM-IM (origin from Rhizomucor miehei), Lipozyme TL-IM (origin from Thermomyces lanuginosus), and Pancreatic Lipase (origin from Porcine Pancreas).

In one or more embodiments, the lipase is selective for the 1-position, the 3-position or both positions in a glyceride. In one or more embodiments, the lipolytic enzyme selective for the 1-position, the 3- position or both positions is selected from Chromobacterium viscosum, dog gastric lipase, dog 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, Pseudomonas fluorescens lipase, Pseudomonas glumae lipase, porcine pancreatic lipase, Penicillium simplicissimum lipase, Rhizopus arrhizus lipase, rabbit gastric lipase, Fusarium heterosporum lipase, Candida rugosa lipase, and variants thereof.

In one or more embodiments, the lipase is non-selective for the positions in a glyceride.

In one or more embodiments, the process further comprises the step (vii) of separating the mono-, di- and/or triglyceride from the second liquid fraction.

Monoglycerides are used as emulsifying agents in many food products, such as whipped cream, baked goods, and ice cream.

In one or more embodiments, the lipase is selective for the 1-position, and the 3-position in a glyceride, and wherein the process further comprises the step (vii) of separating the formed monoglyceride from the second liquid fraction.

Diglycerides are used as common food additives used to blend together certain ingredients, such as oil and water. Furthermore, both mono- and diglycerides are recommended as aerating agents and shelf-life extenders in bakery margarines and shortenings. They are also used as aerating agents in ice cream and imitation creams.

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

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

It is anticipated that the lipolytic enzyme specificities mentioned above (both saturated/unsatu rated specificity as well as 1,3 specificity) will be high at a low degree of conversion which will decrease concurrently with the depletion of the preferred substrate and the simultaneously increase of the less preferred substrate. Hence, it is preferred to run the reaction at low conversion in order to secure the highest possible specificity. It is an advantage in certain embodiments of the invention to make the best utility of all reaction products, even at low conversion rates of transesterification.

In one or more embodiments, the invention relates to a process, wherein the conversion in transesterification to mono-ester glycolipid and mono- or di-glyceride is below 5%, below 10%, below 15%, below 20%, below 25%, below 30%, below 35%, below 40%, below 45% or below 50%.

In one or more embodiments, the invention relates to a process, wherein the conversion in transesterification to mono-ester glycolipid and mono- or di-glyceride is at least 40%, at least 45%, at least 50%, at least 55%, at least 60%, at least 65%, or at least 70%.

In one or more embodiments, the invention relates to a process, wherein the lipase is selective for saturated fatty acids, preferably a lipase selected from Candida antarctica lipase A, Fusarium oxysporum lipase, and variants thereof.

The separation method for purifying mono- or di-glyceride 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 may be removed as the volatile fraction by deodorization, evaporation or distillation. This volatile fraction can further be separated into alcohol (optionally for reuse in step (I)) and the unreacted free fatty acid or fatty acid ester, which may be reused in step (VI). Deodorisation is essentially a steam distillation under vacuum and is well known in the art. A deodorizer may be operated at 0.15 mbar, 225° C. with steam dosage of 0.20% to 0.25% w/w per hour. Other modes of operation are known in the art, see e.g., 'Introduction to Fats and Oil Technology', Eds O'Brien, Farrr and Wan, AOCS Press, 2000 chapter 13.

The methods of distillation and evaporation are also known in the art. Evaporation units for oils are usually vapor distillation units, called deodorizers. For step (VIII) it is an embodiment to use distillation under high vacuum to minimize thermal damage. It is in certain embodiments of the invention preferred to use a system with multiple equilibrium stages to achieve a good separation. Other preferred embodiments include Falling film Molecular Distillators operated at pressures of 0.001 to 10 mmHg and temperatures of 140- 200 degrees Celsius, or Centrifugal Molecular Distillators which can operate at pressures around 0.001-10 mmHg and temperatures of 160- 240 degrees Celsius (both of these modes are described in detail in Batistella et al, Appl. Biotechn., vol. 98, 1149-1159, 2002). It is possible to use direct or indirect heating, and it is possible to operate in batch and/or continuous operation. The transesterification may preferably be performed at a temperature within the range of 20-95 degrees Celsius, depending on the optimal conditions for the lipase to work, such as within the range of 30-85 degrees Celsius, e.g., within the range of 40-75 degrees Celsius, such as within the range of 50-65 degrees Celsius, e.g., at about 60 degrees Celsius.

The transesterification may preferably be performed for a period in the range of a few minutes, such as five minutes, to several hours, such as 120 hours, depending on the reaction times of the used reactants.

Preferred solvents used in the transesterification reaction are tert-amyl alcohol, acetone, tert-butanol, 1-propanol, isopropanol, isobutanol, and isoamyl alcohol.

Purification of the produced glycolipid may be done by standard methods, such as extraction, filtration through a mesoporous adsorbent or filter, affinity or adsorption based chromatographic methods with various solvents, distillation of possible remaining volatile solvents, and centrifugal isolation of precipitated product, by-products, or reactants. Suitable solvents for chromatographic methods may e.g., be water, methanol, ethyl acetate, ethanol, pentane, hexane, heptane, acetone, methyl ethyl ketone, dichloromethane, tert-amyl alcohol and 1-propanol.

The disclosed production method for the mono-ester glycolipid is an exemplary, but preferred, method. Other methods are also contemplated by the present invention.

Another aspect relates to a mono-ester glycolipid produced by the process according to the present invention.

Yet another aspect relates to a mono- and/or diglyceride produced by the process according to the present invention.

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

Examples

Example 1 - production of mono-ester glycolipids

Mono- or disaccharide was added to a stirring vessel together with the chosen solvent to make a 10% w/w dispersion. Oil was then added under stirring to achieve a molar ratio of 1 : 1 for oil and saccharide. The lipase was added in a concentration of 10% w/w (compared to saccharide mass). The reaction mixture was heated to 60 degrees Celsius and stirred for 120 hours. Product formation was detected by TLC analysis and afterwards purified using column chromatography by eluting with DCM:MeOH.

Example of solvents tested and used: tert-amyl alcohol, acetone, tert-butanol, 1-propanol, isopropanol, isobutanol, and isoamyl alcohol.

Example of lipases tested and used : Candida antarctica B lipase, Lipozyme RM-IM (origin from Rhizomucor miehei), Lipozyme TL-IM (origin from Thermomyces lanuginosus).

Mono-ester glycolipids have been synthesized based on maltose, sucrose, cellobiose, trehalose, galactose, and glucose. The other 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 the used carbohydrate was xylose and lactose.

This shows that not all saccharides are behaving the same way, despite having a similar or identical chemical composition, as is commonly known for carbohydrates. For example, maltose, sucrose, and lactose all have the composition (C12H22O11) but out of these three, the synthesis only proved successful with sucrose and maltose.

The mono-ester glycolipids synthesized based on monosaccharides (glucose and galactose) were only soluble in water to a very low degree and could therefore not be used for the subsequent testing in the following examples.

Example 2 - comparison of laundry detergent compositions

A series of four laundry detergent compositions were made where only one component differed from one another. Three (#1, #3, and #4) different commercial non-ionic surfactants were chosen to test against a mono-ester glycolipid (#2, SBS1) according to the present invention.

SBS1 is a mono-ester glycolipid with a carbohydrate moiety being maltose and a lipid moiety being oleic acid (6- and/or 6'-oleyl-maltose).

D-Glucopyranose, oligomers, decyl octyl glycosides can be bought under the trade name Triton CG-110. Triton CG-110 is a nonionic surfactant used in laundry detergent compositions, and it is known for its mildness. Its chemical group is also known as alkyl polyglucoside.

Secondary alcohol (C12-C14) ethoxylate 31EO can be bought 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.

Decaethylene glycol monododecyl ether belongs to the class of nonionic surfactants, and is often 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 "decaethylene"). This structure gives it distinct surface-active properties. The different detergents are tested for their detergency, wetting ability, foaming ability, and emulsification capacity.

Detergency

Method

The detergency measurement consists of soiling a swatch fabric with sunflower oil and washing it with a formulation. Swatches of fabric are cut out in 7x7 cm. 10 mL of sunflower oil is diluted to 100 mL with dichloromethane. Swatches are folded and submerged in the solution for 5 min at room temperature., unfolded and then dried overnight. The swatches are weighed on a scale before and after to determine the amount of oil deposited. Washing is performed with a 1000 mL washing solution that was made by diluting 50 mL of detergent formulation to 1000 mL with deionized water (approximately 1% total surfactants). 4 swatches in 1 chamber were washed at the same time as replicates. Agitation speed was set to 200 rpm and washing time 20 minutes at room temperature. A 10-minutes rinse with 1000 mL deionized water was performed right after the washing cycle also at room temperature. The post wash swatches were dried to completion before determining detergency. Detergent efficiency is given by a percentage of oil removal and a higher value indicates better detergency.

Results

The formulation comprising mono-ester glycolipid (#2, SBS1) performs better on cotton fabric than the formulations with commercial surfactants and shows comparable effect on the cotton/polyester blend.

Foaming Method

The foaming ability and stability is measured by mixing and determining foam height after t=l and t=30 min. For the test 5 mL of the desired surfactant formulation was used in a 1 :200 dilution (approximately 0.1% total surfactants) and were performed in triplicates. This was added into a 15 mL centrifuge tube with screw cap. Foaming was initiated by handshaking the tube for 10 sec and letting it settle for 50 sec. The foam height was measured to time=l min giving the foam ability. The sample was set to rest, and the foam height measured at time=30 minutes. The foam stability is determined by the ratio of the foam heights at time=l minute and time=30 minutes.

Results

The formulation with mono-ester glycolipid (#2, SBS1) performs with equal effect as the formulations with commercial surfactants. Laundry detergents should preferably be relatively low foaming. The compound used in formulation #1 is considered a low foaming surfactant.

Emulsification index - E24

Method

The emulsification index (E24) was measured by mixing the surfactant formulation with an oil and measuring the height of emulsion to determine the ability of the formulation to dissolve hydrocarbons. For a test, 5 mL 1 :200 water dilution of the surfactant formulation (approximately 0.1% total surfactants) and 5 mL either paraffin oil (low viscosity), sunflower oil, olive oil, or frying oil were added to a 15 mL centrifuge tube. The tests were performed in triplicates. Formulation dilutions are mixed by hand shaking the tube at room temperature for 10 seconds and set to rest at room temperature. The E24 is determined by the ratio of the height of the emulsion to the total volume height 24 hours after mixing. A similar procedure was used for palm oil (refined) except first the solid palm oil was heated to 40 degrees to melt. After mixing the sample was set to rest for 24 hours while keeping the temperature constant at 35 degrees before measuring E24 as described before.

Results

The formulation with mono-ester glycolipid (#2, SBS1) performs with better, or comparable effect as the formulations with commercial surfactants.

Draves test - Wetting ability

Method

The wetting ability is measured by the time it takes for a skein of cotton to sink into a surfactant solution. Good wetting ability helps water to adhere to the surface of the fabric, remove air, and facilitate removal of oil and dirt from the surface. A faster sinking time indicates better wetting ability. A 1 :200 water dilution of each of the surfactant formulations (approximately 0.1% total surfactants) is prepared for the test. 600 mL were loaded into a measuring cylinder and a 5 g 100% cotton skein attached to a hook and weight with a string were dropped in. The time it takes for the string to loosen was defined as the wetting time. The tests were performed in triplicates.

Results

The formulation with mono-ester glycolipid (#2, SBS1) performs with better effect than the formulations with commercial surfactants.

Breakthrough test - Wetting ability

Method

The wetting ability was measured by the time it takes for a drop of surfactant formulation to penetrate through an oil disk. 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 Oil Red O to the oil and stirring for 1 hour to secure a homogeneous distribution. Small crystallization dishes of 0 70 mm were used for the test done in triplicates. For each test, 35 g water was poured into the dish. 2.5 grams of the dyed oil were slowly added on top, thereby forming a thin disc. A 5 microliter drop of 1 : 1 (approximately 10% total surfactants) diluted formulation was delicately deposited in the middle of the oil disc with a finnpipette. The breakthrough time was measured from the deposition till the opening of the oil disc.

Results

The formulation with mono-ester glycolipid (#2, SBS1) performs with equal effect as the formulations with commercial surfactants.

Example 3 - comparison of laundry detergent compositions

Additional three laundry detergent compositions were made using glycolipids. Again, only one component differed from one another and a similar composition to the one in Example 2 was chosen. The three additional mono-ester glycolipid compositions (#5 SBS2, #6 SBS3, and #7 SBS4) together with #2 (SBS1) were tested against the commercial nonionic surfactant formulations (#1, #3, and #4). SBS2 is a mono-ester glycolipid with a carbohydrate moiety being sucrose and a lipid moiety being oleic acid (6- and/or 6'-oleyl- sucrose). SBS3 is a mono-ester glycolipid with a carbohydrate moiety being trehalose and a lipid moiety being oleic acid (6- and/or 6'-oleyl-trehalose). SBS4 is a mono-ester glycolipid with a carbohydrate moiety being cellobiose and a lipid moiety being oleic acid (6- and/or 6'-oleyl-cellobiose).

Emulsification capacity

Method

The emulsification capacity was measured by mixing the surfactant formulation with an oil and measuring the height of emulsion to determine the ability of the formulation to dissolve hydrocarbons. For a test, 1 mL 1 :200 water dilution of the surfactant formulation (approximately 0.1% total surfactants) and 1 mL either sunflower oil, maize oil or rapeseed oil were added to a 4 mL vial with screw cap. The tests were performed in triplicates. Formulation dilutions were vortexed for 20 sec and set to rest at room temperature. The emulsification capacity is determined by the ratio of the height of the emulsion to the total volume height after 10 min, 1 hour, 2 hours and 3 hours after mixing.

Results The 4 formulations with mono-ester glycolipids, #2 (SBS1), #5 (SBS2), #6 (SBS3) and #7 (SBS4) perform with equal effect as the formulations with commercial surfactants.

Furthermore, the mono-ester glycolipids made from maltose, trehalose, and cellobiose perform equally well as the mono-ester glycolipid made from sucrose despite the large difference in solubility of the disaccharide on its own.

Example 4 - Effect of different amount of non-ionic surfactant A series of four laundry detergent compositions were made to test the effects of the nonionic surfactants at different concentrations when replacing an anionic surfactant. This is done by replacing a part of LAS (sodium dodecyl benzene sulfonate, an anionic surfactant) present in the composition described earlier in example 1 and 2 with either the commercially available alkyl polyglycoside (APG) (Triton CG-110) or a mono-ester glycolipid (#2, SBS1) according to the present invention. Increase in concentration was made by a 30% reduction/substitution of LAS (#8 and #9), and another with about 60% reduction/substitution of LAS (#10 and #11).

The different formulations are tested for their detergency, wetting ability, foaming ability, and emulsification capacity using the same protocols as described in example 2. Detergency

Results

At a 30% increase in non-ionic surfactants, the mono-ester glycolipid (SBS1) and commercial APG (Triton CG-110) are showing comparable detergency effect. However, at a 60% increase in non-ionic surfactants the detergency effect of the mono-ester glycolipid (SBS1) formulation is performing better than the commercial APG (Triton CG-110) for both 100% cotton and cotton/polyester blend. Foaming

Results

For both a 30% and 60% increase in non-ionic surfactants, the mono-ester glycolipid (SBS1) performs with better effect than the commercial non-ionic APG (Triton CG-110) as laundry detergents should preferably be relatively low foaming.

Emulsification index - E24

Results

At a 30% increase in non-ionic surfactants the mono-ester glycolipid (SBS1) and commercial APG (Triton CG-110) show comparable emulsion capacities. When increasing to 60%, the emulsification effect of the mono-ester glycolipid (SBS1) formulation performs better than the commercial APG (Triton CG-110).

Draves test - Wetting ability

Results

The wetting times shows that the commercial APG (Triton CG-110) has a slightly better wetting ability for both the formulations with a 30% and 60% increase in non-ionic surfactant concentration when compared to the mono-ester glycolipid (SBS1).

Example 5 - Enzymatic activity The lipolytic activity was monitored using a pro-chromogenic substrate, p-nitrophenyl buryrate. Briefly, different surfactant: lipase mixtures in 50 mM Tris 50 mM NaCI pH 8 buffer with an enzyme concentration of 10 nM are incubated at 25°C for 10 min prior to the analysis to ensure stable temperature. The substrate is then injected from a stock solution of 15 mM to a final concentration of 0.12 mM and the chromogenic product release is monitored by measuring the absorbance at 405 nm for several minutes using a Clariostar plate reader (BMG LABTECH, Ortenberg, Germany). The activity is then determined as the resulting slope of the linear range by linear regression and normalized to the activity of lipase in the buffer. The experiment was performed in triplicates. The enzyme used is a lipase purified using dialysis and ion exchange chromatography (to ensure interactions only between surfactants and enzyme), from the commercial formulation Lipex® Evity® 200 L (Novozymes), which is made for laundry detergents. Lipex® Evity® 200 L is a variant of the Thermomyces lanuginosa lipase family. The used surfactants are shown in the table below, and the results are shown in Figure 1.

The normal concentration of surfactant during washing is at least 200 mg/L. The data show that the enzyme loses activity with the presence of small amounts of surfactants. Most of the tested commercial surfactants result in a lipase activity of 5-10% above 200 mg/L. Triton APG results in an intrapolated lipase activity of 70% at 200 mg/L, but the lipase activity rapidly declines at higher concentrations. The mono-ester glycolipid (SBS1) results in a surprising increase in lipase activity from 100 mg/L and upwards and outperforms Triton APG at about 800 mg/L (intrapolated value). This indicates that the mono-ester glycolipid (SBS1) is a better choice for future laundry detergents for washing machines utilizing less water than current machines. Furthermore, as SBS1 gives a relative increase in activity of the lipase at higher concentrations, it indicates that SBS1 is mild towards enzymes and is likely compatible with other enzyme types such as proteases, amylases, cellulase that can be part of laundry detergent formulations.

Claims

1. Use of a mono-ester glycolipid or a mixture of mono-ester glycolipids in a laundry detergent composition; characterized in that said mono-ester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety selected from the group consisting of maltose, cellobiose, trehalose, isomaltulose, lactulose, isomaltose, and mixtures thereof.

2. The use according to claim 1, wherein said disaccharide is derived from polysaccharides, such as starch, e.g., by enzymatic cleavage.

3. The use according to claim 1, wherein said mono-ester glycolipid or mixture of monoester glycolipids comprises a carbohydrate moiety selected from the group consisting of maltose, cellobiose, trehalose, and mixtures thereof.

4. The use according to claim 1, wherein said mono-ester glycolipid or mixture of monoester glycolipids comprises a carbohydrate moiety being maltose.

5. The use according to any one of the claims 1-4, wherein said mono-ester glycolipid comprises a lipid moiety derived from a diglyceride and/or triglyceride selected from a source consisting of: sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, tallow, lard, rice bran oil, coconut oil, linseed oil, mango oil, Kalahari melon seed oil, almond oil, poppy seed 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 the claims 1-4, wherein said mono-ester glycolipid comprises a lipid moiety having a chain length within the range of C6-C26, 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 palmitelaidic acid and/or palmitoleic acid.

7. The use according to any one of the claims 1-4, wherein said mono-ester glycolipid comprises a lipid moiety having a chain length within the range of C16-C18, 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 palmitelaidic acid and/or palmitoleic acid.

8. A laundry detergent composition comprising:

- a mono-ester glycolipid or a mixture of mono-ester glycolipids; characterized in that said mono-ester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety 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, where the enzyme is a lipase.

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

12. The laundry detergent composition according to any one of the claims 8-11, wherein said mono-ester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety selected from the group consisting of maltose, sucrose, lactose, cellobiose, trehalose, and mixtures thereof.

13. The laundry detergent composition according to any one of the claims 8-11, wherein said mono-ester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety being maltose.

14. The laundry detergent composition according to any one of the claims 8-13, wherein said mono-ester glycolipid comprises a lipid moiety derived from a diglyceride and/or triglyceride selected from a source consisting of: sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, tallow, lard, rice bran oil, coconut oil, mango oil, Kalahari melon seed oil, almond oil, poppy seed oil, plum kernel oil, grapeseed oil, apricot kernel oil, linseed oil, palm oil, shea butter, shea butter oil, and mixtures thereof, preferably derived from sunflower oil.

15. The use according to any one of the claims 8-13, wherein said mono-ester glycolipid comprises a lipid moiety having a chain length within the range of C6-C26, 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 palmitelaidic acid and/or palmitoleic acid.

16. The use according to any one of the claims 8-13, wherein said mono-ester glycolipid comprises a lipid moiety having a chain length within the range of C16-C18, 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 palmitelaidic acid and/or palmitoleic acid.

17. A method for cleaning textiles and/or textile articles comprising the steps of: - providing a laundry detergent composition comprising a mono-ester glycolipid or a mixture of mono-ester glycolipids, in a concentration to effectively clean fabrics/textile articles under predetermined laundering conditions;

- allowing the textiles and/or textile articles to dry, or mechanically tumble-drying them; characterized in that said mono-ester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety selected from the group consisting of maltose, cellobiose, trehalose, isomaltulose, lactulose, isomaltose, and mixtures thereof.