CN120858167A

CN120858167A - Use of monoester glycolipids in laundry detergents

Info

Publication number: CN120858167A
Application number: CN202480017080.3A
Authority: CN
Inventors: 卡斯珀·泰勒斯菲尔·奥勒森·法尔肯贝格; 丹尼尔·林德·詹森; 尼克拉斯·霍伊布罗·诺加尔
Original assignee: Norfolk Ltd
Current assignee: Norfolk Ltd
Priority date: 2023-03-09
Filing date: 2024-01-02
Publication date: 2025-10-28
Also published as: WO2024183958A1

Abstract

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

Description

Use of monoester glycolipids in laundry detergents

Technical Field

The present invention relates to laundry detergents.

Background

Laundry detergents are a composition used to remove unwanted materials from textiles/laundry during the cleaning process. The most important class of compounds in laundry detergents are surfactants, also known as surfactants. The surfactant includes hydrophilic and hydrophobic portions, which make it suitable for diffusion in water and to adsorb at the interface between water and unwanted substances on the textile. In brief, the surfactant molecules herein will be aligned and encapsulated around the unwanted material, thereby releasing it from the textile to form micelles, with the unwanted material residing within the micelles.

By varying the hydrophilic and/or hydrophobic portions, properties such as wetting ability, foaming ability and dispersing ability can be adjusted. Surfactants thus differ in their ability to remove certain types of unwanted materials, their effect on different types of textiles, and their response to water hardness.

The surfactants currently used have been shown to be very effective. However, consumer demand for new milder and "more environmentally friendly" laundry detergents means that there is a need for new research in this area.

Disclosure of Invention

It is therefore an object of the present invention to provide a more environmentally friendly alternative to currently used laundry detergents.

The inventors of the present invention have discovered the use of a novel subtype of nonionic surfactant, monoester glycolipid, which is a more environmentally friendly alternative to traditional nonionic surfactants in laundry detergents.

The inventors of the present invention have also discovered a process for producing monoester glycolipids from renewable sources such as enzymatically hydrolyzed starch (e.g., maltose) and used edible oils (e.g., sunflower oil, canola oil, corn oil, and olive oil). Furthermore, these monoester glycolipids are biodegradable. Part of the by-products (mono-and diglycerides) can even be separated out as valuable food ingredients or food additives.

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

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

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

-providing a laundry detergent composition comprising a monoester glycolipid or a mixture of monoester glycolipids in a concentration effective to clean a fabric/textile article under predetermined wash conditions;

Contacting one or more textiles and/or textile articles with the laundry detergent composition at one or more nodes during a wash process, and

-Allowing the textile and/or textile article to dry, or subjecting them to mechanical drum drying.

The present invention will be described in more detail below.

Detailed Description

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

The first aspect relates to the use of a monoester glycolipid or a mixture of monoester glycolipids in a laundry detergent composition.

The inventors of the present invention have discovered a process for producing monoester glycolipids from renewable resources.

The laundry detergent compositions of the present invention may take any of a variety of forms. It may 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 molded solid, or any other laundry detergent form known to those skilled in the art.

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

Application method

A method of cleaning a textile and/or textile article is described in detail below, including the steps of, without limitation:

i. providing a laundry detergent composition comprising a monoester glycolipid or a mixture of monoester glycolipids in a concentration effective to clean fabric and/or textile articles under predetermined wash conditions;

Allowing the textile and/or textile article to dry or subjecting them to mechanical drum drying.

The amount of laundry detergent composition typically ranges from between about 10g to about 300g of total product per 3kg of textile article, depending on the particular embodiment selected and other factors affecting the use behavior of the product, such as consumer preference.

A consumer using the present invention may contact a textile article, such as clothing, with the composition of the present invention according to specific instructions for the purpose of simultaneously cleaning and softening the textile article. This is recommended when the composition is in the form of a softening detergent and needs to be added at the beginning of the cleaning cycle.

In addition to the monoester glycolipids described above, formulators have included one or more optional ingredients in laundry detergent compositions. Although the presence of these elements is not necessarily required to practice the present invention, the use of such materials generally contributes significantly to making the formulation of laundry detergent compositions more acceptable to consumers.

Examples of optional components include, but are not limited to, anionic surfactants, nonionic surfactants, amphoteric and zwitterionic surfactants, cationic surfactants, co-solvents, optical brighteners, photobleaches, fiber lubricants, reducing agents, enzymes, enzyme stabilizers, powder finishes, defoamers, builders, bleaches, bleach catalysts, soil release agents, anti-redeposition agents, dye transfer inhibitors, buffers, colorants, perfumes, pro-fragrances, rheology modifiers, anti-ash polymers, preservatives, insect repellents, anti-soil agents, water repellents, suspending agents, sensory modifiers, structurants, disinfectants, solvents, fabric finishes, color fixatives, anti-wrinkle agents, fabric conditioners, and deodorants.

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 enzyme may include cellulases, hemicellulases, peroxidases, proteases, glucoamylases, amylases, lipases, cutinases, pectinases, xylanases, mannanases, pectate lyases, reductases, oxidases, phenol oxidases, lipoxygenases, ligninases, pullulanases, tannase, pentosanases, maltases, beta-glucanases, arabinosidases, or mixtures thereof.

A preferred combination is a laundry detergent composition having a mixture of conventionally suitable enzymes, such as proteases, amylases, lipases, cutinases and/or cellulases, combined with a lipolytic enzyme variant D96L at a level of 50LU to 8500LU per liter of cleaning solution.

Preferred lipases are selected from the family of Thermomyces lanuginosus (Thermomyces lanuginosa) lipases. The family of thermophilic mould lanuginoses refers to the group of lipases mainly derived from the thermophilic fungus Thermomyces lanuginosus. These enzymes are known for their ability to break down lipids (fats) and have several unique properties such as thermostability and substrate specificity.

Suitable cellulases include both bacterial cellulases and fungal cellulases. Preferably, its optimal pH is between 5 and 9.5. Suitable cellulases are disclosed in U.S. Pat. No. 4,435,307, which discloses fungal cellulases produced by Humicola insolens (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), in particular Humicola strain DSM 1800. Other suitable cellulases are those derived from Humicola insolens having a molecular weight of about 50,000 and an isoelectric point of 5.5 and containing at least 415 amino acid units. Particularly suitable cellulases are cellulases having color care effects. An example of such a cellulase is the cellulase described in European patent application number 91202879.2. Preferred commercially available cellulases include those sold under the trade name Novozymes A/SCellulases sold under the trade name IFFCellulases sold under the trade name AB EnzymesCellulases are sold.

Peroxidases are typically used in combination with an oxygen source, such as 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 a substrate during a cleaning operation to other substrates in the cleaning solution. Peroxidases are enzymes known in the art and include, for example, horseradish peroxidase, lignin enzymes, and haloperoxidases such as chloroperoxidase and bromoperoxidase. Peroxidase-containing detergent compositions are disclosed, for example, in PCT International patent application WO 89/099813 and European patent application 91202882.6.

Cellulases and/or peroxidases are typically incorporated into the laundry detergent composition at levels of from 0.0001% to 2% active enzyme by weight of the laundry detergent composition.

Preferred commercially available proteases include those sold under the trade name Novozymes A/S AndSold under the trade name of Gist-BrocadesAndSold protease, protease sold by GenencorInternational, under the trade name Solvay EnzymesAndSold protease under the trade name IFFAndSold protease under the trade name AB EnzymesROC 250 LCO. Other proteases described in U.S. patent 5,679,630 may also be included in the detergent composition.

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

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

Highly preferred enzymes that may be included in the detergent composition include lipases. It was found that the cleaning effect on greasy dirt was synergistically enhanced by using lipase. Lipases are enzymes that catalyze the hydrolysis of fats and oils to fatty acids and glycerol, mono-and/or diglycerides. Suitable lipases for use herein include those of animal, plant, fungal and microbial origin. Suitable lipases can be present in cambium, bark, plant roots, as well as in seeds of fruits, oil palm, lettuce, rice, bran, barley and malt, wheat, oat and oat flour, cotton seed, corn, millet, coconut, walnut, sickle cell, hemp and cucurbit (cucurbit). In addition to naturally occurring lipases, chemically modified or protein engineered mutants may also be used.

Suitable lipases include those derived from microorganisms of the genus Humicola (also known as Thermomyces), for example those derived from Humicola lanuginosa (H.Lanuginosa) (Thermomyces lanuginosus) (see, for example, EP 258 068 and EP 305 216), or those derived from Humicola insolens (H.insolens) (see, for example, PCT International application WO 96/13580), pseudomonas (Pseudomonas) lipases, for example those derived from Pseudomonas alcaligenes (P.alcaligenes) or Pseudomonas alcaligenes (P.pseudoalcaligenes) (see, for example, EP 218272), pseudomonas cepacia (P.cepacia) (see, for example, EP 331376), pseudomonas schnei (P.stzeri) (see, for example, no. 1,372,034), pseudomonas fluorescens (P.fluorons), pseudomonas sp (see, for example, WO 96/13580), bacillus sp (see, for example, bacillus sp. Pseudobacillus) or Bacillus sp (P.pseudoalcaligenes) (see, for example, WO 96/96), bacillus sp (see, for example, bacillus sp. Pseudobacillus sp. 2702) or Bacillus sp. Sp (WO 96/96).

Lipase variants, such as those described in U.S. patent nos. 8,187,854, 7,396,657, and 6,156,552, the entire contents of which are incorporated herein by reference, may be used. Other lipase variants are also described in PCT International application WO 92/05249、WO 94/01541、WO 95/35381、WO 96/00292、WO 95/30744、WO 94/25578、WO 95/14783、WO 95/22615、WO 97/04079 and WO 97/07202, as well as in EP 0 407 225 and EP 0260105.

Suitable lipases include those sold under the trade names LipexTM、LipolexTM、LipocleanTM、LipolaseTM、Lipolase UltraTM、LipopanTM、Lipopan XtraTM、LypozymeTM、PalataseTM、ResinaseTM、NovozymTM 435 and LipoprimeTM (both from Novozymes). Other suitable lipases are available as Lipase P AmanoTM (Amano Pharmaceutical). Further suitable lipases are lipases such as M1 LipaseTM and LipomaxTM (DSM), lumafastTM (Danisco) and Preferenz L (IFF). Preferred lipases include D96L lipolytic enzyme variants of the natural lipase derived from Humicola lanuginosa (Humicola lanuginosa), as described in U.S. Pat. No. 6,017,871. Preferably, humicola lanuginosa strain DSM 4106 is used.

The lipase may be used at any suitable level. Typically, the lipase is present in the laundry detergent composition in an amount of from 10 to 20000LU/g, or even from 100 to 10000LU/g of the detergent composition. LU units of lipase activity are defined in WO 99/42566. In the cleaning solution, the lipase dosage is typically 0.01 to 5mg/L of active lipase protein, more typically 0.1 to 2mg/L. The lipase may be used in the detergent in an amount of 0.00001 to 2wt.%, typically 0.0001 to 1wt.%, or even 0.001 to 0.5wt.%, in weight percent.

The lipase may be incorporated into the detergent in any convenient form, such as dust-free particles, stabilized liquids or protected (e.g. coated) particles.

For further examples of suitable lipases for use 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. patent application publication No. 2011/0212877, the teachings of which are incorporated herein by reference.

Amylases (alpha and/or beta) may be included for removal of carbohydrate-based stains. Suitable amylases are(Novozymes)、(Novozymes)、Amylases (Novozymes), stainzyme(Novozymes)、(Novozymes)、(Novozymes)、(IFF)(IFF)。

The enzymes mentioned above may be derived from any suitable source, such as plant, animal, bacterial, fungal and/or yeast sources. See U.S. Pat. No. 5,929,022, the teachings of which are incorporated herein by reference, most of the discussion above being derived from this patent. Preferred compositions optionally comprise a combination of enzymes or mono-enzymes, each typically in an amount ranging from 0.0001% to 2%.

Other enzymes and materials for use with enzymes are described in PCT International patent application No. WO99/05242, which is incorporated herein by reference.

Builders are often added to fabric cleaning compositions to complex and remove alkaline earth metal ions which bind to anionic surfactants and remove them from the cleaning liquid, thereby interfering with the cleaning performance of the detergent. Preferred compositions of the present invention, particularly when used as a detergent/softener combination, contain a builder.

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

Alkali metal carbonates and alkaline earth metal carbonates, such as those detailed in German patent application 2,321,001 (published 11, 15 1973), are suitable for use as builders in the compositions of the present invention. They may be supplied and used in anhydrous form or in a form that includes bound water. Particularly useful is sodium carbonate, or soda ash, which is readily available in the commercial market and has excellent environmental characteristics.

The sodium carbonate used in the present invention may be natural or synthetic and may be used in either a heavy or light form depending on the formulation requirements. Trona is typically mined as trona (trona) and further refined to a specific purity that meets the product's use requirements. On the other hand, synthetic soda ash is generally produced by the Solvay process (Solvay process), or as a byproduct of other manufacturing processes such as caprolactam synthesis. It is sometimes more useful to include small amounts of calcium carbonate in the builder formulation, which can act as seeds to promote crystal formation and thereby enhance the builder effect.

Organic detergency builders may also be used as non-phosphate builders in the present invention. Examples of organic builders include alkali metal citrates, succinates, malonates, fatty acid sulfonates, fatty acid carboxylates, nitrilotriacetates (nitrilotriacetates), oxo disuccinates, alkyl disuccinates and alkenyl disuccinates, oxo diacetates, carboxymethoxy succinates, ethylenediamine tetraacetate, tartaric acid monosuccinate, tartaric acid disuccinate, tartaric acid monoacetate, tartaric acid diacetates, oxidized starches, oxidized heteropolysaccharides, polyhydroxysulfonates, polycarboxylates (such as polyacrylates, polymaleates, polyacetates, polyhydroxyacrylates, polyacrylates/polymaleates 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, oxo disuccinates, acrylate/maleate copolymers and acrylate/maleate/vinyl alcohol terpolymers are particularly preferred non-phosphate builders.

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

However, phosphates are often difficult to formulate, particularly as liquid products, and have been identified as potential factors that may lead to eutrophication of lakes and other waterways. Thus, preferred compositions of the present invention comprise phosphate in an amount of less than about 10% by weight, more preferably less than about 5% by weight. Most preferred compositions of the present invention are formulated to be substantially free of phosphate builder.

Zeolites may also be used as builders in the present invention. The zeolite suitable for incorporation into the products of the present disclosure for use by formulators is a wide variety of zeolite types, including the common 4A zeolite. In addition, the MAP series of zeolites can also be used for incorporation, such as the zeolite taught in European patent application EP 384,070B, which is commercially available under the trade name DoucilA from, for example, ineos Silicos (UK). MAP is defined as an alkali metal aluminosilicate of the P-type zeolite having a silica to alumina 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.

Especially preferred are MAP type zeolites having a silica to alumina ratio of no more than 1.07, more preferably about 1.00. The particle size of the zeolite is not critical. Any suitable particle size type a zeolite or MAP zeolite may be used. However, in any event, since zeolite is an insoluble material, it is advantageous to minimize its content in the composition of the present invention. Thus, preferred formulations contain less than about 10% zeolite builder, while particularly preferred compositions include less than about 5% zeolite.

When enzymes, particularly proteases, are used in liquid detergent formulations, it is often desirable to include an appropriate amount of enzyme stabilizer to temporarily inactivate the enzyme prior to cleaning use. 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 particularly suitable for use as enzyme stabilizers because, in addition to this effect, they can buffer the pH of the detergent product over a wide range, providing excellent flexibility.

If a borate-based enzyme stabilization system is selected and one or more cationic polymers containing at least partially carbohydrate moieties are used simultaneously, stability problems may occur without the use of an appropriate co-stabilizer. It is believed that this is due to the natural affinity of borates for hydroxyl groups, which may form insoluble borate-polymer complexes that may precipitate out of solution over time or at low temperatures. This is generally prevented by incorporating a co-stabilizer (which is typically a glycol or polyol, sugar or other molecule having a large number of hydroxyl groups) in the formulation. Sorbitol is particularly preferably used as a co-stabilizer at a level of at least about 0.8 times the borate level in the system, more preferably 1.0 times the borate level in the system, and most preferably more than 1.43 times the borate level in the system. Sorbitol is good in effect, low in cost, biodegradable and easy to obtain in the market. Similar materials, including sugars such as glucose and sucrose, and other polyols such as propylene glycol, glycerol, mannitol, maltitol, and xylitol, are also considered to be within the scope of the present invention.

To enhance conditioning, softening, anti-wrinkling and protective effects of the compositions of the present invention, it is often desirable to include one or more fibrous 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 during and after the cleaning process of the article being treated. This effect in turn improves consumer perception of softness, minimizes the formation of wrinkles, and prevents damage to the textile during the cleaning process. For the purposes of this disclosure, "fiber lubricant" is understood to be a non-cationic material that is intended to lubricate the fibers, with the purpose of reducing friction between the fibers or yarns in an article comprising a textile, thereby providing one or more anti-wrinkle, fabric conditioning or protective effects.

Examples of suitable fibrous lubricants include oily saccharide derivatives, functionalized animal and vegetable derived oils, silicone oils, mineral oils, natural and synthetic waxes, and the like.

Oily saccharide derivatives suitable for use in the present invention are taught in WO 98/16538, which is incorporated herein by reference. Such materials are particularly preferred as fiber lubricants because of their readily available and environmentally friendly nature. When used in the compositions of the present invention, such materials are typically present in the finished composition at levels between about 1% and about 10%. Another acceptable class of ingredients includes hydrophilically modified vegetable and animal oils and synthetic triglycerides. Suitable and preferred hydrophilically modified vegetable, animal and synthetic triglyceride oils and waxes have been identified as effective fiber lubricants. Such suitable plant-derived triglyceride materials include hydrophilically modified triglyceride oils (e.g., sulfated, sulfonated, carboxylated, alkoxylated, esterified, glycosylation-modified, and amide-derivatized oils), tall oil (talloil), derivatives thereof, and the like. Suitable animal derived triglyceride materials include hydrophilically modified fish oils, tallow, lard, lanolin wax, and the like. A particularly preferred functionalized oil is sulfated castor oil, which is commercially available, for example, under the trade name Freedom SCO-75 from Noveon corporation (Cleveland, ohio).

Different degrees of derivatization may be used provided that the degree of derivatization is sufficient to render the oil or wax derivative soluble or dispersible in the solvent used to exert a fiber lubricating effect during the washing of fabrics with a detergent comprising the oil or wax derivative.

If the invention comprises a functionalized oil of synthetic origin, it is preferred that the oil is a silicone oil. More preferably, it is a silicone polyether or an amino-functional silicone.

In many liquid and powder detergent compositions, co-solvents are often added to adjust the product viscosity and prevent phase separation in the liquid and the powder is easily dissolved. Two classes of co-solvents are commonly used in detergent formulations and are suitable for use in the present invention. The first is a short chain functionalized amphiphilic molecule. Examples of short chain amphiphilic molecules include alkali metal salts of xylenesulfonic acid, cumene sulphonic acid, and octyl sulphonic acid, and the like. In addition, organic solvents, as well as mono-and polyols having a molecular weight below about 500, such as, for example, ethanol, isopropanol, acetone, propylene glycol, and glycerol, may also be used as co-solvents.

To prevent recontamination of the fabric during and after cleaning, one or more soil release agents may also be added to the product of the present invention. Those skilled in the art are familiar with a variety of different types of soil release agents, the particular choice being dependent upon the formulation used and the effect desired. Soil release agents useful in the context of the present invention are typically anti-redeposition aids or anti-fouling 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 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 of the present invention found that, possibly due to steric hindrance, only C6-alcohol reacts with fatty acid when the carbohydrate is glucose, whereas C6-alcohol or C6' -alcohol reacts with fatty acid when the carbohydrate is maltose. In one or more embodiments, the monoester glycolipid or mixture of monoester glycolipids includes a carbohydrate moiety that is maltose.

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

In one or more embodiments, the monoester glycolipid or mixture of monoester glycolipids includes a disaccharide carbohydrate moiety derived from a polysaccharide such as starch, for example by enzymatic cleavage.

In one or more embodiments, the monoester glycolipid or mixture of monoester 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 its balance between hydrophilic head groups and hydrophobic tail groups. For monoester glycolipids this corresponds to the hydrophilicity of the carbohydrate moiety and the hydrophobicity of the hydrocarbon moiety. For disaccharides, their solubility in water (and thus hydrophilicity) can differ by up to an order of magnitude (as shown in the table below). This makes it difficult to predict whether surfactants made from these different disaccharides exhibit similar properties and are suitable as surfactants in laundry detergent formulations.

Disaccharides	Solubility in water (g/mL)
		Sucrose	2.1
Maltose	1.1
		Lactose and lactose	0.19
Trehalose	0.69
		Cellobiose	0.12
Isomaltose	0.5
		Isomaltulose	0.29
Lactulose	0.76

In one or more embodiments, the monoester glycolipid includes lipid moieties derived from diglycerides and/or triglycerides selected from the group consisting of sunflower seed 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), mango oil, kara Ha Ligua seed oil, almond oil (almond oil), poppy seed oil, plum seed oil, grape seed oil, apricot kernel oil (apricot kerneloil), and mixtures thereof. The most common fatty acids present in many of the oils described above are oleic, linoleic, stearic and palmitic (as evident from the table below), and therefore the lipid fraction is predominantly one of these four fatty acids.

The term "glyceride" (also referred to as acylglycerol) as used herein refers to a monoglyceride, diglyceride, triglyceride, or a combination thereof. They are esters formed from glycerol and fatty acids. The glycerides in the oil may include a variety of saturated, unsaturated fatty acids. The term "triglyceride" as used herein refers to an ester formed 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 formed from glycerol and two fatty acids, and the term "monoglyceride" refers to an ester formed from glycerol and one fatty acid.

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

The term "fatty acid" as used herein refers to molecules derived from triglycerides, which include carboxylic acids having long aliphatic tails (chains), which may be saturated or unsaturated. When unattached to other molecules, they are referred to as "free" fatty acids. Most naturally occurring fatty acids have chains with an even number of carbon atoms, from 4 to 28. Short Chain Fatty Acids (SCFA) refer to fatty acids having fewer than six carbon atoms in the aliphatic tail. Medium Chain Fatty Acids (MCFA) refer to fatty acids with an aliphatic tail of 6-12 carbon atoms, which can form medium chain triglycerides. Long Chain Fatty Acids (LCFA) refer to fatty acids having an aliphatic tail of 13 to 21 carbon atoms. Very Long Chain Fatty Acids (VLCFA) refer to fatty acids with aliphatic tails longer than 22 carbon atoms. In one example, the fatty acid or ester thereof may include at least 10, at least 12, at least 14, at least 16, at least 18, or at least 20 carbon atoms. In certain embodiments, the fatty acid or ester thereof 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, any of which may be used as an upper or lower limit where appropriate. In other examples, the glycerides may include a mixture of fatty acids or esters thereof having different ranges of carbon atoms.

In a preferred embodiment, the monoester glycolipid comprises a lipid moiety with a carbon chain length in the range of C6-C26, which may be saturated or unsaturated, with 1-6 double bonds, preferably 1-3 double bonds, such as 1-2 double bonds. More preferably, the carbon chain length is in the range of C10-C18. More preferably, the carbon chain length is in the range of C16-C18.

In one or more embodiments, the monoester glycolipid or mixture of monoester glycolipids comprises a carbohydrate moiety that is maltose, and wherein the monoester glycolipid comprises a lipid moiety derived from a diglyceride and/or triglyceride selected from sunflower seed oil sources.

In one or more embodiments, a monoester glycolipid or a mixture of monoester glycolipids includes a carbohydrate moiety that is maltose, and wherein the monoester glycolipid includes a lipid moiety having a carbon chain length in the range of C6-C26, which may be saturated or unsaturated, unsaturated having 1-6 double bonds. More preferably, the carbon chain length is in the range of C10-C18. More preferably, the carbon chain length is in the range of C16-C18.

In one or more embodiments, the monoester glycolipid or mixture of monoester glycolipids comprises a carbohydrate fraction that is maltose and wherein the monoester glycolipid comprises a lipid fraction derived from diglycerides and/or triglycerides selected from the group consisting of sunflower seed oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, tallow, lard, rice bran oil, coconut oil, mango oil, kara Ha Ligua seed oil, almond oil, poppy seed oil, plum seed oil, grape seed oil, apricot kernel oil, linseed oil, palm oil, shea butter, and mixtures thereof, preferably derived from sunflower seed oil.

Another aspect of the invention relates to a process for producing a monoester glycolipid, comprising the steps of:

(i) Dispersing and/or dissolving 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 lipase in the starting mixture under stirring;

(iv) Transesterifying the carbohydrate with the diglyceride and/or triglyceride at a temperature between 0-100 degrees celsius to form a first liquid fraction and a first solid fraction, the first liquid fraction comprising the polar organic solvent, monoester glycolipid, glycerol, and monoglycerides, diglycerides, and/or triglycerides, and the first solid fraction comprising lipase and optionally unreacted carbohydrate;

(v) Separating the first liquid fraction from the first solid fraction, and

(Vi) The monoester glycolipid is separated from the first liquid fraction to form a second liquid fraction comprising monoglycerides, diglycerides and/or triglycerides and glycerol.

The core is the use of lipases to catalyze transesterification between carbohydrates and diglycerides and/or triglycerides to form monoester glycolipids and glycerides (i.e. mono-or diglycerides, respectively) with a reduced number of bound fatty acids. Depending on the type of lipase, diglycerides (diacylglycerols) can be used as substrates to carry out new reactions with another carbohydrate molecule to form monoester glycolipids and monoglycerides. Also, depending on the lipase used, monoglycerides (monoacylglycerols) may be used as substrates for a new reaction with another carbohydrate molecule to form monoester glycolipids and glycerols. In the present context, the term "transesterification" refers to a chemical reaction of an ester compound, i.e. an alkoxy group of a diglyceride and/or a triglyceride (and optionally a subsequently formed monoglyceride), with another alkoxy group in the presence of a catalyst (i.e. a lipase), by reacting the ester with an alcohol (i.e. a carbohydrate).

Since each lipase has a different specificity for fatty acids, it is important to select an appropriate lipase according to the fatty acid type of glyceride. If non-regiospecific (i.e., all fatty acids can be cleaved/transferred from glycerides) is desired, lipases with non-regiospecificity are selected. Suitable examples may be, for example, candida antarctica (CANDIDA ANTARCTICA) type B lipase, lipase OF (derived from Candida rugosa), lipase G (derived from Candida rugosa), lipase AYS (derived from Candida rugosa), lipase PS (derived from burkholderia cepacia (Burkholderia cepacia)), lipase AK (derived from pseudomonas fluorescens (Pseudomonas fluorescens)), lipase AS (derived from aspergillus niger (Aspergillus niger)), and lipase M (derived from mucor javanicum (Mucor javanicus)). If regiospecificity is desired (i.e., only some fatty acids can be cleaved/transferred from the glyceride), a lipase with regiospecificity is selected. Suitable examples with 1, 3-region specificity may be, for example, lipase F-AP15 (derived from Rhizopus oryzae), lipase Newlase F G (derived from Rhizopus niveus (Rhizopus niveus)), lipase R (derived from Penicillium lanuginosum (Penicillium roqueforti)), lipozyme RM-IM (derived from Rhizomucor miehei (Rhizomucor miehei)), lipozyme TL-IM (derived from Thermomyces lanuginosus), and pancreatic lipase (derived from porcine pancreas).

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

In one or more embodiments, the lipolytic enzyme selective for position 1,3 or both is selected from the group consisting of a Bacillus mucilaginosus (Chromobacterium viscosum), a dog gastric lipase, a dog pancreatic lipase, a Fusarium solani (Fusarium solani) cutinase, a guinea pig pancreatic lipase, a human gastric lipase, a Humicola lanuginosa lipase, a human pancreatic lipase, a lipoprotein lipase, a Mucor miehei lipase, a Pseudomonas aeruginosa (Pseudomonas aeruginosa) lipase, a Kappy Bai Qingmei lipase, a Pseudomonas fluorescens lipase, a Pseudomonas glumae (Pseudomonas glumae) lipase, a pig pancreatic lipase, a Penicillium (Penicillium simplicissimum) lipase, a Rhizopus oligosporus (Rhizopus arrhizus) lipase, a Fusarium gastric lipase, a Pseudomonas cepacia (Fusarium heterosporum) lipase, a Candida rugosa lipase, and variants thereof.

In one or more embodiments, the lipase is not selective for the position in the glyceride.

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

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

In one or more embodiments, the lipase is selective for the 1-and 3-positions in the glycerides, and wherein the process further comprises step (vii) separating the formed monoglycerides from the second liquid fraction.

Diglycerides are common food additives used to blend certain ingredients, such as oil and water. Furthermore, both monoglycerides and diglycerides are recommended as shortening and shelf life extenders in baking margarines and shortenings. They are also used as a shortening in ice cream and imitation cream.

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

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

It is expected that the above mentioned lipolytic enzyme specificities (saturated/unsaturated specificity and 1, 3-position specificity) will be higher at low conversion rates, with a concomitant increase in the consumption of the preferred substrate and less preferred substrate, with a concomitant decrease in the specificity. Thus, it is preferred to carry out the reaction at low conversion to ensure the highest possible specificity. In certain embodiments of the invention, all reaction products are fully utilized, even at low conversion of transesterification, which is advantageous.

In one or more embodiments, the invention relates to a process wherein the conversion to monoester glycolipids and transesterification of 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%.

In one or more embodiments, the present invention relates to a process wherein the conversion to monoester glycolipids and the transesterification of 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%.

In one or more embodiments, the present 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 (Fusarium oxysporum) lipase and variants thereof.

The separation method for purifying mono-or diglycerides from the first liquid fraction may be selected from deodorization, distillation, evaporation or any combination thereof. The presence of fatty acid esters or free fatty acids can be removed as volatile fractions by deodorization, evaporation or distillation. The volatile fraction may be further separated into an alcohol (optionally for reuse in step (I)) and unreacted free fatty acids or fatty acid esters, which may be reused in step (VI). Deodorization is essentially steam distillation under vacuum, which is well known in the art. The deodorizer can be operated at 0.15mbar, 225 ℃ with steam addition of 0.20% to 0.25% w/w per hour. Other modes of operation are also known in the art, see for example "Introduction to Fats and Oil Technology", eds O' Brien, FARRR AND WAN, AOCS press, chapter 13 of 2000.

Methods of distillation and evaporation are also known in the art. The evaporation device for oil is typically a steam distillation unit, called a deodorizer. For step (VIII), the use of high vacuum distillation is one embodiment to minimize thermal damage. In certain embodiments of the present invention, it is preferred to use a system with multiple balancing stages to achieve good separation. Other preferred embodiments include falling film molecular distillers operating at pressures of 0.001 to 10mmHg and temperatures of 140-200 degrees Celsius, or centrifugal molecular distillers operating at pressures of about 0.001-10mmHg and temperatures of 160-240 degrees Celsius (both modes are described in detail in Batistella et al, appl. Biotech., vol.98,1149-1159,2002). Direct or indirect heating may be used and batch and/or continuous operation may be performed.

Preferably, the transesterification may be carried out at a temperature in the range of 20-95 degrees celsius, such as in the range of 30-85 degrees celsius, for example in the range of 40-75 degrees celsius, such as in the range of 50-65 degrees celsius, for example at about 60 degrees celsius, depending on the optimal conditions under which the lipase is to function.

The period of time during which transesterification is carried out may preferably be in the range of a few minutes, such as five minutes, to several hours, such as 120 hours, depending on the reaction time of the reactants used.

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

The glycolipids produced can be purified by standard methods such as extraction, filtration through mesoporous adsorbents or filters, chromatography with various solvents based on affinity or adsorptivity, distillation of volatile solvents that may remain, and separation of the precipitated products, byproducts, or reactants by centrifugation.

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

The disclosed monoester glycolipid production process is an exemplary, but preferred process. Other methods are contemplated by the present invention.

Another aspect relates to a monoester glycolipid produced by the process according to the invention.

Yet another aspect relates to monoglycerides and/or diglycerides produced by the process of the present invention.

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

Examples

EXAMPLE 1 production of monoester glycolipid

The mono-or disaccharides are added to a stirred vessel along with the selected solvent to make up a 10% w/w dispersion. The oil was then added with stirring to bring the molar ratio of oil to sugar to 1:1. Lipase was added at a concentration of 10% w/w (compared to the sugar mass). The reaction mixture was heated to 60 degrees celsius and stirred for 120 hours. The product formation was detected by TLC analysis and subsequently purified using column chromatography, eluting with DCM: meOH.

Examples of solvents tested and used are t-amyl alcohol, acetone, t-butyl alcohol, 1-propanol, isopropanol, isobutyl alcohol and isoamyl alcohol.

Examples of lipases tested and used are candida antarctica type B lipase, lipozyme RM-IM (from rhizomucor miehei), lipozyme TL-IM (from thermomyces lanuginosus).

Monoester glycolipids have been synthesized based on maltose, sucrose, cellobiose, trehalose, galactose and glucose. The other reactant is selected from sunflower oil, rapeseed oil, olive oil, frying oil (i.e. a mixture of sunflower oil, rapeseed oil and corn oil), shea butter. When xylose and lactose were used as the carbohydrates, the experiment was unsuccessful.

This suggests that not all saccharides show the same behaviour, although they have similar or identical chemical compositions, which is well known in carbohydrates. For example, maltose, sucrose and lactose all have the composition (C ₁₂H₂₂O₁₁), but of these three sugars, synthesis was successful only for sucrose and maltose.

Monoester glycolipids synthesized based on monosaccharides (glucose and galactose) have extremely low solubility in water and thus cannot be used for subsequent testing in the following examples.

Example 2 comparison of laundry detergent compositions

A series of four laundry detergent compositions were prepared in which only one ingredient was different from the other. Three different commercial nonionic surfactants (# 1, #3 and # 4) were selected for comparison testing with monoester glycolipids (# 2, SBS 1) according to the invention.

SBS1 is a monoester glycolipid with a carbohydrate fraction of maltose and a lipid fraction of oleic acid (6-and/or 6' -oleoyl-maltose).

D-glucopyranose, oligomer, decyl octyl glycoside are commercially available under the trade name Triton CG-110. Triton CG-110 is a nonionic surfactant used in laundry detergent compositions and is known for its mildness. The chemical class is also known as alkyl polyglucosides.

Secondary alcohol (C12-C14) ethoxylate 31EO is commercially available 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 secondary alcohols of C12-14 ethoxylated to an average of 31 Ethylene Oxide (EO) units.

The dodecyl alcohol monolauryl ethers belong to the class of nonionic surfactants and are commonly used in laundry detergent compositions. It is formed by ethoxylation of dodecanol with ethylene oxide, resulting in a molecule having ten ethylene oxide units (hence the name "decaethylene glycol"). This structure imparts unique surface active properties.

The detergency, wetting ability, foaming ability and emulsifying ability of the different detergents were tested.

Detergency power

Method of

The detergency test consisted of staining a cloth-like fabric with sunflower seed oil and then washing with the formulation. The fabric swatches were cut to 7x7 cm. 10mL of sunflower seed oil was diluted to 100mL with methylene chloride. After folding the cloth sample at room temperature, it was immersed in the solution for 5min, then spread and dried overnight. The swatches were weighed before and after contamination, respectively, to determine the amount of oil deposited. The wash was performed using 1000mL of wash solution made by diluting 50mL of the detergent formulation with deionized water to 1000mL (about 1% total surfactant). As a repeat experiment, 4 swatches were washed simultaneously in the same 1 chamber. At room temperature, the stirring speed was set at 200rpm and the washing time was 20 minutes. Immediately after the rinse cycle, a 10 minute rinse was performed with 1000mL deionized water at room temperature. The detergency was measured after the washed swatches were completely dried. The detergent efficiency is expressed as percent oil removal, with higher values indicating better detergency.

Results

Formulations comprising monoester glycolipids (# 2, sbs 1) perform better on cotton fabrics than formulations with commercial surfactants and also perform quite well on cotton/polyester blends.

Foaming

Method of

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

Results

The formulation with monoester glycolipid (# 2, sbs 1) shows comparable effects to the formulation with commercial surfactant. Laundry detergents generally preferably have relatively low sudsing. The compound used in formulation #1 is considered a low foaming surfactant.

Emulsion index-E24

Method of

The emulsification index (E24) is measured by mixing the surfactant formulation with oil and measuring the height of the emulsion to determine the ability of the formulation to dissolve hydrocarbons. For testing, 5mL of a 1:200 aqueous dilution of the surfactant formulation (about 0.1% total surfactant), and 5mL of paraffin oil (low viscosity), sunflower oil, olive oil, or frying oil were added to a 15mL centrifuge tube. The test was performed in triplicate. The tube was manually shaken at room temperature for 10 seconds to mix the formulation dilutions and then allowed to stand at room temperature. E24 is defined as the ratio of the emulsion height to the total volume height 24 hours after mixing. For palm oil (refining), a similar procedure is used, but first the solid palm oil is heated to 40 degrees to melt it. After mixing, the sample was left to stand at 35℃for 24 hours, and then E24 was measured as before.

Results

Formulations with monoester glycolipids (# 2, sbs 1) perform better than or equivalent to formulations with commercial surfactants.

Draves test-wetting ability

Method of

The wettability is measured by the time required for the cotton skein to sink into the surfactant solution. Good wetting ability aids water adhesion to the fabric surface, vents air, and facilitates removal of oil and dust from the surface. The faster the settling time, the better the wetting ability. At the time of testing, each surfactant formulation was prepared as a 1:200 aqueous dilution (about 0.1% total surfactant). 600mL of the dilution was loaded into a graduated cylinder, 5g of 100% cotton skein was attached to a hook and weight with a rope, and then poured into solution. The time required for the rope to relax is defined as the wetting time. The test was performed in triplicate.

Results

The formulation with monoester glycolipid (# 2, sbs 1) showed better effect than the formulation with commercial surfactant.

Breakthrough test (Breakthrough test) -wetting ability

Method of

The wetting ability is measured by the time required for a drop of surfactant formulation to penetrate the oil film. The sunflower seed oil used for the test was first colored red to better visualize the breakthrough point. This is done by adding 0.05% w/w oil red O (OilRed O) to the oil and stirring for 1 hour to ensure even dye distribution. Test useIs performed in triplicate. At each test, 35g of water was poured into the dish. Then 2.5 grams of dyed oil was slowly added on top to form a thin disc. 5 microliter 1:1 (about 10% total surfactant) diluted formulation droplets were carefully deposited in the middle of the oil pan (oil disc) with a pipette. The breakthrough time is measured as cracking from deposition to oil pan.

Results

The formulation with monoester glycolipid (# 2, sbs 1) shows comparable effects to the formulation with commercial surfactant.

Example 3 comparison of laundry detergent compositions

Three other laundry detergent compositions were prepared using glycolipids. Also, only one component was different from each other among these compositions, and a composition similar to that in example 2 was selected. Three additional monoester glycolipid compositions (# 5SBS2, #6SBS3, and #7SBS 4) were tested in comparison with the commercial nonionic surfactant formulations (# 1, #3, and # 4) along with #2 (SBS 1). SBS2 is a monoester glycolipid with a carbohydrate moiety of sucrose and a lipid moiety of oleic acid (6-and/or 6' -oleoyl-sucrose). SBS3 is a monoester glycolipid with a carbohydrate moiety of trehalose and a lipid moiety of oleic acid (6-and/or 6' -oleoyl-trehalose). SBS4 is a monoester glycolipid with a carbohydrate moiety of cellobiose and a lipid moiety of oleic acid (6-and/or 6' -oleoyl-cellobiose).

Emulsifying capacity

Method of

The emulsifying capacity is measured by mixing a surfactant formulation with oil and measuring the height of the emulsion to determine the ability of the formulation to dissolve hydrocarbons. For testing, 1mL of a 1:200 aqueous dilution of the surfactant formulation (about 0.1% total surfactant), and 1mL of sunflower, corn or canola oil were added to 4mL capped vials. The test was performed in triplicate. The formulation dilution was vortexed for 20sec and allowed to stand at room temperature. The emulsifying capacity was determined by the ratio of the emulsifying height to the total volume height after 10min, 1 hour, 2 hours and 3 hours after mixing.

Results

The 4 formulations with monoester glycolipids #2 (SBS 1), #5 (SBS 2), #6 (SBS 3) and #7 (SBS 4) exhibited effects comparable to those with commercial surfactants. Furthermore, although disaccharides themselves have a large difference in solubility, monoester glycolipids made from maltose, trehalose, and cellobiose behave quite as monoester glycolipids made from sucrose.

EXAMPLE 4 Effect of different amounts of nonionic surfactant

A series of four laundry detergent compositions were prepared for testing the effect of varying concentrations of nonionic surfactant upon replacement of anionic surfactant. This is achieved by replacing part of the LAS (sodium dodecylbenzenesulfonate, an anionic surfactant) present in the compositions described previously in examples 1 and 2 with commercially available Alkyl Polyglycoside (APG) (Triton CG-110) or monoester glycolipid (# 2, sbs 1) according to the invention. By reducing/replacing LAS by 30% (# 8 and # 9), and reducing/replacing LAS by about 60% (# 10 and # 11), an increase in concentration is achieved.

The detergency, wetting ability, foaming ability and emulsifying ability of the different formulations were tested using the same protocol as described in example 2.

Detergency power

Results

Monoester glycolipid (SBS 1) showed comparable detergency to commercial APG (Triton CG-110) when the nonionic surfactant was increased by 30%. However, the detergency effect of the monoester glycolipid (SBS 1) formulation was better than commercial APG (Triton CG-110) when the nonionic surfactant was increased by 60%, either on 100% cotton or cotton/polyester blends.

Foaming

Results

The monoester glycolipid (SBS 1) exhibits better performance than commercial nonionic APG (Triton CG-110) whether the nonionic surfactant content is increased by 30% or 60%, because the laundry detergent should preferably be relatively low sudsing.

Emulsion index-E24

Results

Monoester glycolipid (SBS 1) showed comparable emulsifying capacity with commercial APG (Triton CG-110) when the nonionic surfactant was increased by 30%. The emulsifying effect of the monoester glycolipid (SBS 1) formulation was superior to commercial APG (Triton CG-110) when increased to 60%.

Draves test-wetting ability

Results

The wetting time shows that commercial APG (Triton CG-110) exhibits slightly better wetting ability in both formulations with 30% and 60% increase in nonionic surfactant concentration, respectively, compared to monoester glycolipid (SBS 1).

EXAMPLE 5 enzymatic Activity

Lipolytic activity was monitored using chromogenic precursor substrate p-nitrobutyrate. Briefly, a mixture of different surfactants, lipase, was placed in 50mM Tris, 50mM NaCl, pH 8 buffer at an enzyme concentration of 10nM and incubated at 25℃for 10min before analysis to ensure temperature stability. The substrate was then injected with a stock solution from 15mM to a final concentration of 0.12mM and the release of chromogenic product was monitored by measuring absorbance at 405nm for several minutes using a Clariostar microplate reader (BMG LABTECH, ortenberg, germany). The resulting slope in the linear range is then determined by linear regression, whereby the enzyme activity is determined and normalized to the lipase activity in the buffer. Experiments were performed in triplicate. The enzymes used were those from commercial formulations200L (Novozymes) of lipase extracted from the formulation prepared for use in laundry detergents, which lipase was purified using dialysis and ion exchange chromatography (to ensure only interaction between surfactant and enzyme).200L of variants belonging to the family of Thermomyces lanuginosus lipases. The surfactants used are shown in the table below and the results are shown in figure 1.

Surface active agent	Names in the chart
		Secondary alcohol (C12-C14) ethoxylate 31EO	C12E31
SBS1	SBS1
		Dodecyl glycol ether	C12E10
D-glucopyranose, oligomer and decyl octyl glycoside	Triton APG
		Cocamidopropyl betaine	Cocamidopropyl betaine

The normal concentration of surfactant during the cleaning process is at least 200mg/L. The data show that even in the presence of small amounts of surfactant, the enzyme lost activity. Most of the commercial surfactants tested retained only 5-10% of lipase activity at concentrations above 200mg/L. Triton APG showed 70% lipase activity at 200mg/L, but showed a rapid decrease in lipase activity at higher concentrations. Monoester glycolipid (SBS 1) produced unexpected increases in lipase activity at concentrations of 100mg/L and above and was superior to Triton APG (interpolated value) at about 800 mg/L. This shows that monoester glycolipid (SBS 1) is a better choice for future laundry detergents for washing machines with less water than existing machines. Furthermore, since SBS1 is still relatively enhancing lipase activity at higher concentrations, it is suggested that SBS1 is mildly enzyme-compatible with other enzymes such as proteases, amylases, cellulases that can be used in the laundry detergent formulation portion.

Claims

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

2. Use according to claim 1, wherein the disaccharide is derived from a polysaccharide, such as starch, for example by enzymatic cleavage.

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

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

6. 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-C26, the lipid portion being saturated or unsaturated with 1-6 double bonds, such as oleic acid and/or linoleic acid and/or stearic acid and/or palmitic acid and/or trans-palmitoleic acid and/or palmitoleic acid.

7. 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-C18, the lipid portion being saturated or unsaturated with 1-6 double bonds, such as oleic acid and/or linoleic acid and/or stearic acid and/or palmitic acid and/or trans-palmitoleic acid and/or palmitoleic acid.

8. A laundry detergent composition comprising:

- a monoester glycolipid or a mixture of monoester glycolipids; characterized in that the monoester glycolipid or the mixture of monoester glycolipids comprises a carbohydrate 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 of claim 9, wherein the enzyme is lipase.

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

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

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

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

15. 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-C26, the lipid portion being saturated or unsaturated with 1-6 double bonds, such as oleic acid and/or linoleic acid and/or stearic acid and/or palmitic acid and/or trans-palmitoleic acid and/or palmitoleic acid.

16. 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-C18, the lipid portion being saturated or unsaturated with 1-6 double bonds, such as oleic acid and/or linoleic acid and/or stearic acid and/or palmitic acid and/or trans-palmitoleic 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 monoester glycolipid or a mixture of monoester glycolipids at a concentration effective for cleaning fabrics/textile articles under predetermined wash conditions;

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

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