Use of mono-ester glycolipids in personal cleaning product compositions

Abstract

The present invention relates to the use of a mono-ester glycolipid or a mixture of mono-ester glycolipids in personal cleaning product compositions.

Description

[0001] Use of mono-ester glycolipids in personal cleaning product compositions

[0002] Technical field of the invention

[0003] The present invention relates to emulsifiers for personal cleaning products.

[0004] Background of the invention

[0005] Personal cleaning products, such as shampoos, body washes, and face cleansers, typically consist of several base components. Each component plays a specific role in the overall formulation, contributing to the product's efficacy, safety, and user experience. The exact formulation can vary widely depending on the type of product, its intended use, and the brand's philosophy (e.g., natural, organic, hypoallergenic). The primary base components are surfactants, water, moisturizers and conditioners, thickeners and stabilizers, pH adjusters, and emulsifiers. Other components may be specialty additives, preservatives, fragrances, and dyes. The surfactants are responsible for cleaning and forming lather. Lather is the frothy foam formed when the surfactants are mixed with water and air, typically through agitation (like rubbing or shaking). They reduce surface tension, allowing the product to spread easily and trap dirt and oils. Water acts as a solvent, diluting other ingredients and facilitating their application and distribution. Moisturizers and conditioners help to keep the skin and hair hydrated, thereby counteracting the potential drying effects of the surfactants. Thickeners and stabilizers provide the desired consistency and stability to the personal cleaning product, while pH adjusters maintain the product's pH at a level that is safe and effective for skin and hair. Surfactants and emulsifiers, while closely related and often overlapping in their roles and chemical nature, are not always the same. They are typically selected from different types of chemicals based on their specific functions in a product formulation. While the role of surfactants is discussed above, the emulsifiers are present to stabilize the emulsion by reducing the surface tension between the oil and water phases. Examples include anionic, cationic, and non-ionic emulsifiers. Non-ionic emulsifiers are generally preferred for products designed for sensitive skin due to their mildness. Cationic emulsifiers are preferred for hair conditioners because of their conditioning properties. Anionic emulsifiers are often chosen for their ability to interact with dirt and oils, making them effective in cleansers and scrubs. Hence, surfactants and emulsifiers can be chemically similar and sometimes even the same compound can perform both roles. However, they are typically selected and used based on their primary function in a product - surfactants for cleansing and foaming, and emulsifiers for stabilizing mixtures of oil and water.

[0006] One of the mayor concerns when formulating an personal cleaning product is its ability to form the lather to allow the product to spread easily and trap dirt and oils. Currently used surfactants are shown to be very effective. However, consumer demands for new milder and "greener" skin- and haircare products mean that this area needs to be addressed again.

[0007] Summary of the invention

[0008] Thus, an object of the present invention is to provide a green alternative to the currently used surfactants for the formation of lather.

[0009] The inventors of the present invention have found use of a new subtype of non-ionic surfactants, mono-ester glycolipids, that is a green alternative to conventional anionic and non-ionic surfactants for personal cleaning products.

[0010] 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 (glycerol and mono- and diglycerides) may even be separated as valuable food ingredients or food additives or kept together with the mono-ester glycolipids to be used as emulsifiers, moisturizers, and / or thickeners in the personal cleaning product.

[0011] Thus, a first aspect relates to the use of a mono-ester glycolipid or a mixture of monoester glycolipids in personal cleaning products.

[0012] A second aspect relates to a personal cleaning product composition comprising a monoester glycolipid or a mixture of mono-ester glycolipids.

[0013] A third aspect relates to a personal cleaning product composition comprising :

[0014] - water;

[0015] - a moisturizer and / or conditioner; and

[0016] - a mono-ester glycolipid or a mixture of mono-ester glycolipids. A fourth aspect relates to a process for producing a personal cleaning product composition comprising :

[0017] (i) dispersing and / or solubilizing a carbohydrate in a polar organic solvent in a reaction vessel;

[0018] (ii) adding a diglyceride and / or triglyceride to said reaction vessel to form a starting mixture;

[0019] (iii) dispersing a lipase in said starting mixture under stirring;

[0020] (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, and mono-, di- and / or triglyceride, and a first solid fraction comprising lipase and optionally unreacted carbohydrate;

[0021] (v) separating the first liquid fraction from the first solid fraction;

[0022] (vi) removing said polar organic solvent from said first liquid fraction to form a second liquid or solid fraction; and

[0023] (vii) adding water and moisturizer and / or conditioner to said second liquid or solid fraction to form a personal cleaning product composition.

[0024] Preferably, the mono-ester glycolipid or mixture of mono-ester glycolipids comprises an unmodified carbohydrate moiety.

[0025] An unmodified carbohydrate is here defined as a carbohydrate in its closed form, whose functionalities, apart from the anomeric acetal / hemicacetal, only consist of hydroxyl groups and does not have any of these replaced, either naturally or chemically by another functionality such as an amino, alkoxy, carboxylate, or acetyl group.

[0026] The present invention will now be described in more detail in the following. Detailed description of the invention

[0027] Glycolipids are amphiphilic, non-ionic molecules that comprises a hydrophilic carbohydrate moiety and one or more fatty acids as the lipophilic moiety. Mono-ester glycolipids has a single fatty acid as the lipophilic moiety. The inventors of the present invention have found that mono-ester glycolipids have comparable or even better properties than conventional anionic and non-ionic surfactants.

[0028] The primary base components of personal cleaning product compositions are surfactants, water, and moisturizers and conditioners. Other components may be thickeners and stabilizers, pH adjusters, emulsifiers, specialty additives, preservatives, fragrances, and dyes.

[0029] As discussed in the background section, the surfactants are responsible for cleaning and forming lather. Lather is the frothy foam formed when the surfactants are mixed with water and air, typically through agitation (like rubbing or shaking). They reduce surface tension, allowing the product to spread easily and trap dirt and oils. A non-limiting list of surfactants commonly used in personal cleaning products are: Sodium Laureth Sulfate, Sodium Lauryl Sulfate, Cocamidopropyl Betaine, Ammonium Laureth Sulfate, Ammonium Lauryl Sulfate, Sodium Cocoyl Isethionate, Sodium Lauroyl Sarcosinate, Decyl Glucoside, Lauryl Glucoside, Sodium Cocoamphoacetate, Disodium Laureth Sulfosuccinate, Coco Glucoside, Sodium Cocoyl Glutamate, Sodium Lauryl Glucose Carboxylate, Lauryl Hydroxysultaine, Sodium Methyl Cocoyl Taurate, Caprylyl / Capryl Glucoside, and Sodium Methyl Oleoyl Taurate. A few of those are discussed further in the Examples section.

[0030] The content of surfactants in personal cleaning products can vary widely depending on the type of product and its intended use. In e.g., shampoos and body washes, these products typically contain a relatively high concentration of surfactants, ranging from 10% w / w to 20% w / w, or sometimes more. The high surfactant content is necessary for effective cleansing of the hair and body, removing oils, dirt, and other impurities. In facial cleansers, the surfactant content can vary. Gentle or sensitive skin formulations might have lower surfactant concentrations around 5% w / w to 10% w / w. More robust cleansers designed for oily skin or deep cleansing might have higher levels, comparable to shampoos. While primarily formulated with conditioning agents, conditioners can also contain surfactants, but usually at lower concentrations compared to shampoos, such as about 1% w / w to 5% w / w, used for emulsifying and stabilizing the product rather than for cleansing. In hand soaps and shower gels, the content can also vary, but typically in the range of about 10% w / w to 15% w / w. The exact amount depends on the desired lather, cleansing ability, and gentleness of the product. Products designed for babies or those with sensitive skin typically have lower surfactant concentrations to minimize the risk of skin irritation. They might contain as little as about 1% w / w to 3% w / w surfactant.

[0031] Water acts as a solvent, diluting other ingredients and facilitating their application and distribution. The percentage of water in a personal cleaning product is influenced by the desired properties of the product, such as viscosity, spreadability, and the concentration of active ingredients. Hence, water not only acts as a solvent but also influences the texture and sensory feel of the product. Typically, the water content is in the range of about 60% w / w to 90% w / w.

[0032] Conditioners and moisturizers are both important in personal care products, but they serve different purposes and function differently, especially when it comes to hair and skin care.

[0033] Conditioners are primarily used in hair care products and are designed to improve the feel, appearance, and manageability of hair. They work by coating the hair shaft to condition the hair, making it smoother, less tangled, and easier to comb. Non-limiting examples of conditioners are cationic surfactants (e.g., cetrimonium chloride), silicones (e.g., dimethicone), and fatty alcohols (e.g., cetyl alcohol). These ingredients adhere to the hair shaft, especially in areas damaged by heat or chemical treatments, to smooth and protect the hair.

[0034] Moisturizers are used in both skin care and hair care products and are aimed at increasing the water content of the skin or hair. They work by either drawing moisture from the environment (humectants like glycerin), sealing moisture into the skin or hair (occlusives like mineral oil), or restoring lipids in the skin (emollients like shea butter).

[0035] Examples of moisturizers include a variety of substances, such as oils, butters, humectants, and emollients. These ingredients can hydrate and soften the skin or hair, and in skin care, they can help restore the skin's barrier function, counteracting the potential drying effects of the surfactants. A non-limiting list of moisturizers and conditioners commonly used in personal cleaning products are: Glycerol, mineral oil, shea butter, cocoa butter, petrolatum, ceramides, hyaluronic acid, dimethicone, lanolin, jojoba oil, coconut oil, argan oil, squalane, panthenol, aloe vera, colloidal oatmeal, vitamin E, cetyl alcohol, stearyl alcohol, behentrimonium chloride, cetrimonium chloride, almond oil, avocado oil, olive oil, sunflower seed oil, glycolic acid, lactic acid, urea, sodium PCA, sorbitol, propylene glycol, caprylic / capric triglyceride, honey, beeswax, mango butter, rosehip oil, sweet almond oil, grapeseed oil, macadamia oil, hemp seed oil, evening primrose oil, borage oil, meadowfoam seed oil, marula oil, squalene, sodium lactate, linoleic acid, linolenic acid, allantoin, silk amino acids, hydrolyzed wheat protein, hydrolyzed soy protein, hydrolyzed keratin, elastin, collagen, snail mucin, beta-glucan, oat kernel oil, rice bran oil, babassu oil, tamanu oil, black seed oil, chia seed oil, pumpkin seed oil, pomegranate oil, sea buckthorn oil, monoi oil, kukui nut oil, murumuru butter, cupuacu butter, illipe butter, polyquaternium-7, polyquaternium-10, amodimethicone, cyclopentasiloxane.

[0036] Glycerin is widely used for its excellent humectant properties, drawing moisture into the skin and hair. Mineral oil is common in a variety of cleaning products for its ability to lock in moisture. Shea butter is valued for its rich, moisturizing properties and is often used in more luxurious formulations. Like shea butter, cocoa butter is known for its deep moisturizing and nourishing properties. Dimethicone is a silicone-based polymer, it's used for its smoothing effect on the skin and hair, and as a protective barrier. Jojoba oil resembles the skin's natural oils, making it an effective moisturizer. Coconut oil is popular for its nourishing properties and is often used in hair cleaning products. Argan oil is known for its restorative and nourishing properties, especially in hair cleaning products. Hyaluronic acid is highly effective as a humectant, attracting and retaining moisture in the skin. Cetyl alcohol and stearyl alcohol are fatty alcohols that are used to thicken and stabilize formulations, also adding moisturizing properties. Panthenol (Pro-Vitamin B5) is common in both skin and hair cleaning products for its moisturizing and softening properties. These ingredients are favoured for their effectiveness in hydrating and conditioning the skin and hair, as well as their compatibility with a wide range of skin types. Each has its own unique benefits, and they are often used in combination to achieve desired effects in personal cleaning products.

[0037] The content of moisturizers and conditioners in personal cleaning products can vary widely based on the product type and its specific formulation. Typically, shampoos contain a lower concentration of moisturizers and conditioners, ranging from 1% w / w to 5% w / w. Some moisturizing or repair shampoos might have slightly higher amounts. Conditioners and hair masks usually have a higher concentration of moisturizers and conditioners, often between 5% w / w to 20% w / w, depending on the product's intended effects (like smoothing, detangling, or deep conditioning). Body washes and shower gels is generally lower than in conditioners, ranging from 1% w / w to 5% w / w. Products marketed for dry skin may contain higher levels. Facial cleansers typically comprise around 1% w / w to 3% w / w, as their primary purpose is cleansing. Formulations for dry or sensitive skin might have slightly higher moisturizer levels to reduce potential dryness post-cleansing. Similar to body washes, hand soaps contain a lower amount of moisturizer, usually around 1% w / w to 3% w / w. However, some hand soaps designed for dry skin might have increased moisturizer content.

[0038] A first aspect relates to the use of a mono-ester glycolipid or a mixture of mono-ester glycolipids in personal cleaning products. Preferably, the mono-ester glycolipid or mixture of mono-ester glycolipids comprises an unmodified carbohydrate moiety. A second aspect relates to a personal cleaning product composition comprising a monoester glycolipid or a mixture of mono-ester glycolipids. Preferably, the mono-ester glycolipid or mixture of mono-ester glycolipids comprises an unmodified carbohydrate moiety.

[0039] A third aspect relates to a personal cleaning product composition comprising :

[0040] - water;

[0041] - a moisturizer and / or conditioner; and

[0042] - a mono-ester glycolipid or a mixture of mono-ester glycolipids.

[0043] A fourth aspect relates to a personal cleaning product composition comprising:

[0044] - 60% w / w to 90% w / w water;

[0045] - 1% w / w to 5% w / w moisturizer and / or conditioner; and

[0046] - 1% w / w to 30% w / w mono-ester glycolipid or a mixture of mono-ester glycolipids.

[0047] In one or more embodiments, the moisturizer and / or conditioner is selected from glycerin, mineral oil, shea butter, cocoa butter, petrolatum, ceramides, hyaluronic acid, dimethicone, lanolin, jojoba oil, coconut oil, argan oil, squalane, panthenol, aloe vera, colloidal oatmeal, vitamin E, cetyl alcohol, stearyl alcohol, behentrimonium chloride, cetrimonium chloride, almond oil, avocado oil, olive oil, sunflower seed oil, glycolic acid, lactic acid, urea, sodium PCA, sorbitol, propylene glycol, caprylic / capric triglyceride, honey, beeswax, mango butter, rosehip oil, sweet almond oil, grapeseed oil, macadamia oil, hemp seed oil, evening primrose oil, borage oil, meadowfoam seed oil, marula oil, squalene, sodium lactate, linoleic acid, linolenic acid, allantoin, silk amino acids, hydrolyzed wheat protein, hydrolyzed soy protein, hydrolyzed keratin, elastin, collagen, snail mucin, betaglucan, oat kernel oil, rice bran oil, babassu oil, tamanu oil, black seed oil, chia seed oil, pumpkin seed oil, pomegranate oil, sea buckthorn oil, monoi oil, kukui nut oil, murumuru butter, cupuacu butter, illipe butter, polyquaternium-7, polyquaternium-10, amodimethicone, cyclopentasiloxane, and mixtures thereof.

[0048] The inventors of the present invention have also found a process for producing mono-ester glycolipids from renewable sources.

[0049] The personal cleaning product composition of the present invention can take any of a number of forms. It can take the form of shampoo, conditioner, body wash, face cleanser, hand soap, shower gel, bubble bath, exfoliating scrub, facial toner, micellar water, makeup remover, dandruff treatment, bar soap, bath oil, intimate wash, or any other personal cleaning product composition form known to those skilled in the art. In one or more embodiments, the mono-ester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety selected from a monosaccharide and / or a disaccharide derived from polysaccharides, such as starch, e.g., by enzymatic cleavage.

[0050] 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, sucrose, lactose, cellobiose, trehalose, isomaltulose, lactulose, and isomaltose.

[0051] 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 glucose, fructose, galactose, mannose, fucose, xylose, ribose, N-acetyl glucosamine, N-acetyl neuraminic acid, arabinose, glucuronic acid, guluronic acid, mannuronic acid, and sialic acid.

[0052] In one or more embodiments, the mono-ester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety, preferably unmodified, selected from the group consisting of maltose, cellobiose, and trehalose.

[0053] In one or more embodiments, the mono-ester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety, preferably unmodified, being maltose.

[0054] In one or more embodiments, the mono-ester glycolipid is either a 6-0-(lipid estermaltose, and / or a 6'-0-(lipid ester)-maltose.

[0055] Preferably, the 6-0-(lipid ester)-maltose and 6'-0-(lipid ester)-maltose is present in a molar ratio of 0.1-10, preferably 0.5-2, even more preferably 0.8-1.2 and most preferably 0.9-1.1.

[0056] 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 moity and the hydrophobicity of the hydrocarbon moity. 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, for example sucrose vs. cellobiose). 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. Furthermore, the table also shows how the solubility is drastically changed (with a factor of around 8) when comparing glucose and methylglucoside (glucose methylated in the 1 position). This shows that properties of surfactants made from unmodified carbohydrates compared to modified glycosylated carbohydrates would be non-trivial to predict beforehand.

[0057] Apart from the solubility, it is also found that self-assembly giving the micellar structure is highly dependent on the isomeric structure of a particular molecule. See for example the article The underlying order: Isomerism as a blueprint to control the behavior of sugar- based (bio)surfactants (Sanchez-Fernandez, Adrian and Poon, Jia-Fei, Current Opinion in Colloid & Interface Science (69), 2024) which shows that a glycosidic bond in alpha or beta configuration will significantly change the micellar structure. Furthermore, it shows that micellar structure varies drastically between an APG based on maltose and lactose due to the H-bonding pattern between the carbohydrates and between the carbohydrate and water. The latter is correlated with the water solubility. Self-assembly and micellar structure are important for personal cleaning products, as larger elongated micelles will give rise to a thickening effects and smaller spherical micelles will give a free-flowing solution. Macroscopic changes in for example feel, texture, viscosity are highly valuable to the consumer experience of these personal cleaning products such as a shampoo, micellar water or a hand soap. Due to these complex H-bonding patterns between carbohydrates and between carbohydrates and water in solution, it is non-trivial even to an expert in the field to predict the self-assembly behaviour of two surfactant with identical molecular structure but different isomeric compositions.

[0058] 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, 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, why the lipid moiety will predominately be one of these four fatty acids.

[0059] In one or more embodiments, the mono-ester glycolipid comprises a lipid moiety derived from oleic acid and / or linoleic acid.

[0060] In one or more embodiments, 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, the chain length is within the range of C8-C18. More preferably the chain length is within the range of C12-C18. Even more preferably the chain length is within the range of C16-C18.

[0061] Preferably, the lipid moity is derived from oleic acid and / or linoleic acid and / or stearic acid and / or palmitic acid and / or palmitelaidic acid and / or palmitoleic acid.

[0062] In one or more embodiments, the mono-ester glycolipid or mixture of mono-ester glycolipids comprises a carbohydrate moiety being maltose.

[0063] 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.

[0064] 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, linseed oil, palm oil, shea butter, shea butter oil, and mixtures thereof, preferably derived from sunflower oil.

[0065] As used herein, the term "carbohydrate" refers to monosaccharides and oligosaccharides. It also includes derivatives of these compounds. As the term "carbohydrate" is used herein, it does not include starch, cellulose and guar, or other polysaccharides with high weight average molecular weights. As defined by the present application, "high weight average molecular weights" are those exceeding about 3000 Daltons. As used herein, the term "oligosaccharide" refers chains of two or more saccharides joined by glycosidic bonds with weight average molecular weight less than about 3000 Daltons. Preferably, the carbohydrate is a monosaccharide, or a disaccharide. Preferred disaccharides may e.g., be maltose, sucrose, lactose, cellobiose, trehalose, and isomaltose. Preferred monosaccharides may e.g., be glucose, fructose, galactose, mannose, fucose, xylose, glucuronic acid, guluronic acid, mannuronic acid, and ribose. Preferably, the monosaccharide and / or 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 using the method specific in example 1.

[0066] In one or more embodiments, the carbohydrate is selected from the group consisting of: maltose, sucrose, lactose, cellobiose, trehalose, isomaltulose, lactulose, isomaltose, and mixtures thereof.

[0067] In one or more embodiments, the carbohydrate is a disaccharide.

[0068] In one or more embodiments, the carbohydrate is selected from the group consisting of: glucose, fructose, galactose, mannose, fucose, xylose, ribose, N-acetyl glucosamine, N- acetyl neuraminic acid, arabinose, sialic acid, glucuronic acid, guluronic acid, mannuronic acid, and mixtures thereof.

[0069] In one or more embodiments, the carbohydrate is a monosaccharide.

[0070] A process for producing mono-ester glycolipids may be as follows:

[0071] (i) dispersing and / or solubilizing a carbohydrate in a polar organic solvent in a reaction vessel;

[0072] (ii) adding a diglyceride and / or triglyceride to said reaction vessel to form a starting mixture;

[0073] (iii) dispersing a lipase in said starting mixture under stirring;

[0074] (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, 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

[0075] (vi) separating the mono-ester glycolipid from the first liquid fraction to form a second liquid fraction comprising mono-, di- and / or triglyceride.

[0076] 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. The different reaction products (glycerine (glycerol) and / or monoglyceride and / or a diglyceride) may be kept together with the produced mono-ester glycolipid as in a subsequent produced personal cleaning product composition, as exemplified in the following process below.

[0077] A fifth aspect relates to a process for producing a personal cleaning product composition comprising :

[0078] (i) dispersing and / or solubilizing a carbohydrate in a polar organic solvent in a reaction vessel;

[0079] (ii) adding a diglyceride and / or triglyceride to said reaction vessel to form a starting mixture;

[0080] (iii) dispersing a lipase in said starting mixture under stirring;

[0081] (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, and mono-, di- and / or triglyceride, and a first solid fraction comprising lipase and optionally unreacted carbohydrate;

[0082] (v) separating the first liquid fraction from the first solid fraction;

[0083] (vi) removing said polar organic solvent from said first liquid fraction to form a second liquid or solid fraction; and (vii) adding water and moisturizer and / or conditioner to said second liquid or solid fraction to form a personal cleaning product composition.

[0084] 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.

[0085] 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, both saturated and 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.

[0086] 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, and mixtures thereof.

[0087] 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 chain length. As each lipase shows different fatty acid specificity (both saturated / unsatu rated specificity as well as 1,3 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).

[0088] In one or more embodiments, the lipase is selective for the 1-position, the 3-position or both positions in a glyceride.

[0089] 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.

[0090] In one or more embodiments, the lipase is non-selective for the positions in a glyceride.

[0091] In one or more embodiments, the process further comprises the step of separating the mono-, di- and / or triglyceride from the second liquid fraction.

[0092] Monoglycerides are used as emulsifying agents in many food products, such as whipped cream, baked goods, and ice cream. 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. Although they are more commonly associated with food products as emulsifiers, monoglycerides may also have a role in personal cleaning products. Monoglycerides can act as emulsifiers, helping to blend and stabilize mixtures of oil and water in products. Like other fatty acid derivatives, monoglycerides can also have a conditioning effect on the skin. They may contribute to the overall texture and viscosity of a product, enhancing its application and feel on the skin or hair. Glycerol is already described as a commonly used moisturizer in personal cleaning product compositions.

[0093] Hence, the different reaction products (glycerol and / or monoglyceride and / or a diglyceride) may be kept together with the produced mono-ester glycolipid in a subsequent produced personal cleaning product composition.

[0094] 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.

[0095] 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%.

[0096] 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%.

[0097] 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.

[0098] 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.

[0099] 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.

[0100] 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.

[0101] 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.

[0102] Preferred solvents used in the transesterification reaction are tert-amyl alcohol, acetone, tert-butanol, 1-propanol, isopropanol, isobutanol, and isoamyl alcohol.

[0103] 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.

[0104] The disclosed production method for the mono-ester glycolipid is an exemplary, but preferred, method. Other methods are also contemplated by the present invention.

[0105] 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

[0106] Example 1 - production of mono-ester glycolipids

[0107] 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 WT% (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.

[0108] Example of solvents tested and used: tert-amyl alcohol, acetone, tert-butanol, 1-propanol, isopropanol, isobutanol, and isoamyl alcohol.

[0109] Example of lipases tested and used : Candida antarctica B lipase, Lipozyme RM-IM (origin from Rhizomucor miehei), Lipozyme TL-IM (origin from Thermomyces lanuginosus).

[0110] Mono-ester glycolipids have been synthesized based on maltose, sucrose, cellobiose, trehalose, galactose, glucose, fructose, and isomaltose. 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.

[0111] A series of five personal cleaning product compositions (see Table 1 below) were made where only one component differed from one another. All five personal cleaning product compositions comprise Sodium LaurEth Sulfate (SLES). SLES is a widely used surfactant in personal care and cleaning products. SLES is primarily used for its detergent properties. It helps to remove dirt, oil, and other impurities from the skin, hair, and other surfaces. It is also responsible for creating lather in products like shampoos, body washes, and facial cleansers. The lather helps to distribute the product evenly and makes the cleaning process more effective and enjoyable for the user. SLES can also assist in mixing water with oil and dirt, allowing them to be rinsed away. This makes it effective in products that need to cleanse oily substances from the skin or hair. Despite its widespread use, SLES has been the subject of scrutiny. It is generally considered less irritating than its close relative, Sodium Lauryl Sulfate (SLS), due to its gentler action on the skin and hair. However, there are still concerns about potential irritation with high concentrations or in sensitive individuals, as well as environmental implications. This has led to the development of SLES alternatives in some natural or organic personal care products. Of the five compositions, the Control has the highest concentration of SLES, while half of the SLES is substituted with another surfactant in compositions #l-#4. Composition #1 was prepared with a mono-ester glycolipid (SBS1), while three different commercial surfactants (caprylyl / capryl glucoside, coco glucoside, and rhamnolipid) were chosen to test against SBS1. 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). Caprylyl / capryl glucoside is a non-ionic surfactant that is used in cosmetic and personal care formulations, including lotions and creams. It is considered to be a gentle and mild emulsifier suitable for sensitive skin. It is typically found in facial cleansers, shampoos, and body washes, especially in products marketed for sensitive skin or natural cosmetics due to its gentle cleansing and foaming properties. Coco glucoside is another non-ionic surfactant that is widely used in personal care and cosmetic formulations. It is derived from coconut oil and glucose, which means it is a natural and biodegradable ingredient. Coco glucoside is valued for its gentle cleansing properties and compatibility with all skin types, making it a staple in formulations aimed at sensitive or delicate skin. It is typically found in baby shampoos, sensitive skin formulations, and natural products. Rhamnolipids are a class of anionic surfactants (pKa around 5.5), which are surface-active substances produced by microorganisms, particularly bacteria of the Pseudomonas genus. They are composed of rhamnose, a naturally occurring sugar, and a 3-(hydroxyalkanoyloxy)alkanoic acid (HAA) fatty acid, such as 3-hydroxydecanoic acid. Due to their microbial origin and biodegradability, rhamnolipids are considered eco-friendly and have gained attention for use in a variety of applications, including the cosmetic industry.

[0112] Apart from the surfactant and water (which e.g., acts as solvent and hydrant), glycerin (glycerol), sodium chloride, citric acid / sodium hydroxide, and potassium sorbate were included in the compositions. Glycerin is an excellent humectant. When applied to the skin, it draws moisture from the environment and the lower layers of skin to the outer layer, keeping the skin hydrated and plump. In hair care products, it helps in maintaining hair moisture, reducing dryness and frizz. Glycerin also functions as a preservative. Sodium chloride is used to adjust the viscosity of products like shampoos and body washes. Adding salt can thicken these products to the desired consistency, making them easier to apply and more appealing to use. Citric acid / sodium hydroxide is present to adjust the pH to an acceptable level. Potassium sorbate is effective at inhibiting the growth of molds, yeasts, and some bacteria. By preventing microbial growth, it extends the shelf life of products and maintains their safety and quality.

[0113] Table 1

[0114] Test methods and results

[0115] Foaming ability

[0116] The foaming properties of personal cleaning products, like shampoos, face washes, and conditioners are a significant aspect of their functionality and consumer appeal. Foam helps in evenly distributing the cleaning agents over the skin or hair. The lather created by foam effectively traps dirt, oil, and other impurities, making it easier to rinse them away. Consumers often associate the amount of foam with the cleaning power of the product. More foam can give a psychological impression of better cleaning and thoroughness. Foam enhances the sensory experience of using the product. It can make the cleansing process feel more luxurious and enjoyable, contributing to the overall user satisfaction.

[0117] The test was performed by adding 50 mL of the personal cleaning product composition to be tested (Control, or one of comp. #l-#4) to a 500 mL measuring cylinder with a diameter of 48 mm. 200 mL of the same personal cleaning product composition is added to a reservoir (500 mL separating funnel) and placed above the measuring cylinder, so the bottom of tip is 80 cm above the solution surface. The funnel is opened, and time starts when the solution has poured out of the reservoir. The height of the foam is afterwards measured at a set time interval of 60s (thl), 180s (th2) and 300s (th3) seconds. All tests were performed in triplicates and the surfactant concentration used in experiments was 0.1%. The results are shown in Table 2 below.

[0118] Table 2

[0119] The foaming tests showed highest foaming for the Control formulation. However only a small difference in height and stability was observed when comparing all formulations. This indicates that SBS1 (#1) can be used in personal cleaning product compositions without disrupting the foaming capabilities, and that it can be used to at least partly substitute SLES.

[0120] Viscosity

[0121] 4 mL of the tested formulation is allowed to flow through a hole, length of 13 mm and 0 2.4 mm, by gravity only. The time for the sample to flow out is measured and used as an indication of the viscosity of the formulation, i.e., the longer the flow time, the higher the viscosity. Two reference fluids (water and a commercial shampoo) were included in the test setup. The tests were performed at room temperature (22 degrees Celsius). The results are shown in Table 3. Surprisingly, SBS1 (#1) also seems to have function as a thickener (viscosity building ingredient), which opens for compositions where additional thickeners are not necessary, thereby avoiding thickeners, such as sodium chloride, xanthan gum, carbomer, and cellulose derivatives.

[0122] Table 3

[0123] Emulsification

[0124] The formulations' emulsification capacity was measured by mixing with paraffin oil and measuring the height of emulsion. For each test, 5 mL formulation (approx, diluted 1 : 1000 with water to a 0.01% total surfactant concentration) and 5 mL paraffin oil (low viscosity) were used. The tests were performed in triplicates. Mixing was done by a vortex mixer for 10 seconds and set to rest. The ratio between the height of the emulsion and the total volume height are measured after respectively 10 minutes and 1 hour.

[0125] The same commercially available surfactants as above were used as benchmarks. Apart from SBS1, two other surfactants, SBS2 and SBS3, were tested. SBS1 is, as described before, a glycolipid with a carbohydrate moiety being maltose and a lipid moiety being oleic acid (6- and / or 6'-oleyl-maltose). 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). The results are shown in Table 4.

[0126] Table 4

[0127] The emulsification data shows similar capacity after both 10 minutes and 1 hour for all compositions / formulations.

[0128] Hence, SBS1-3 seems possible substitutes to the commonly used surfactants, even without loss of emulsion capacity.

[0129] Example 3 - Shampoo

[0130] The sensory profile of the foam generated during washing was tested. Hair tresses of 2.5 cm x 20 cm were wetted with water and 1 mL of shampoo formulation were deposited onto it. Foaming was formed by agitation between the hands and the results were evaluated sensorially and visually. In this example SBS1 was compared to a sucrose ester emulsifier, coco glucoside, rhamnolipid, and Cetearyl glycoside / cetearyl alcohol. SBS1 has shown to be milder compared to the other surfactants in terms of eye-irritation, as SBS1 is the only surfactant that is non-irritant to the eyes. For SBS1, this was investigated by an in vitro study following the guidelines of OECD TG 492B.

[0131] Formulation

[0132] Results

[0133] For formulation #1, #4 and #5 the shampoo gave a good feeling of creamy lather.

[0134] Example 4 - Shampoo without thickener

[0135] A similar formulation to the one used for evaluating the foam in example 3 is used but the thickener, sodium chloride, is replaced with the same amount of glycolipid. Sodium chloride is commonly used in commercial shampoo formulations as a thickener to achieve an acceptable viscosity of the product. Salt can cause product build-up over time, reducing the effectiveness of the shampoo as it alters the texture and consistency. For colour- treated hair, sodium chloride can be particularly damaging, as it opens the hair cuticle, allowing colour to fade more quickly and reducing the overall vibrancy of the hair. In this example, SBS1 was compared to a sucrose ester emulsifier, coco glucoside, rhamnolipid, and Cetearyl glycoside / cetearyl alcohol.

[0136] Formulation

[0137] Results Only for formulation #1 and #2 was it possible to get good viscosity comparable to a commercial shampoo without using sodium chloride. This shows that SBS1 can be used as a bio-based thickener. Example 5 - Facial cleanser

[0138] The ability of SBS1 to function in a facial cleanser was tested by removing waterproof mascara from the skin. A stain of waterproof mascara was applied to the skin and let dry before trying to remove the stain with the facial cleanser. SBS1 was tested with varying concentrations (1.0, 0.5 and 0.2 % Wt. % active).

[0139] Formulation

[0140] Results For all the formulations tested it was possible to remove the waterproof mascara stain even down to 0.2% Wt. % active of SBS1.

[0141] Example 6 - Body wash without thickener

[0142] Similar to the shampoo test without thickener, a bodywash formulation was tested without adding any common thickeners, such as sodium chloride, and xanthan gum. In commercial body washes sodium chloride or xanthan gum are often used to achieve an acceptable viscosity of the product.

[0143] Formulation

[0144] Results

[0145] When formulating, only #1 gave a thick commercially viable consistency, whereas #2 and #3 resulted in a bodywash with a viscosity similar to water. This shows that SBS1 can be used as a bio-based thickener.

[0146] Example 7 - Comparing maltose monoesters with different isomeric composition Maltose monoester was prepared according to the method described in US5550225A, where the isomeric composition is listed as at least 70 percent of monoesters in the 6' position and the remainder being monoester in position 1 (glycosyl ester). This reaction uses mixed carboxylic-carbonic anhydride in an organic solvent medium. SBS1 presented in this patent is produced by an enzyme (more specifically a lipase) producing a mixture of 6 and 6' monoesters. Both products were purified by flash column chromatography before performing the analysis and application tests.

[0147] The two products showed the same retention factor on silica thin layer chromatography with eluent WIPE (1 :2:9), but showed a different isomer composition on HPLC, where it was possible to separate the isomers.

[0148] Results Visually, the maltose monoester produced by the method described in US5550225A was opaque and the SBS1 clear in a 1 mg / mL solution.

[0149] The capacity to dissolve oil droplets was investigated for both products.

[0150] For this test, 4 mL of 0.01% maltose monoester samples were mixed with 4 mL sunflower oil by vortexing for 20 seconds. The emulsion was left for 10 min and a sample of the water phase was removed with a syringe and measured on UV-vis at 660 nm. The test was performed in triplicates. Turbidity was measured 10 min after mixing.

[0151] The blank used was water. As a negative control the water phase of deionized water mixed with sunflower oil was measured.

[0152] This clearly shows that SBS1 is much better at solubilizing oil droplets in the water phase. These measurements were complemented with light microscopy images showing many more emulsions droplets in various sizes for SBS1 compared to maltose monoester from US5550225A. These data clearly show that despite the same molecular formulae, the surfactant properties are highly dependent on the isomeric composition.

[0153] Example 8 - Emulsion capacity of different carbohydrate moieties of SBS1

[0154] The emulsification capacity of different surfactants was tested. For each test 2mL water with 0.01% surfactant and 2mL sunflower oil was used. The tests were performed in triplicates. Mixing was done by a vortex mixer for 20 seconds and set to rest. The ratio between the height of the emulsion and the total volume height are measured after respectively 10 minutes and 1 hour. The commercially available surfactants Rhamnolipid, Coco glucoside and Caprylyl / capryl glucoside were used as benchmarks. Apart from SBS1, three other surfactants, SBS2, SBS3 and SBS4 were tested. SBS1 is, as described before, a glycolipid with a carbohydrate moiety being maltose and a lipid moiety being oleic acid (6- and / or 6'-oleyl-maltose). 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).

[0155] The emulsification data shows similar capacity after both 10 minutes and 1 hour for all the surfactants tested except SBS2.

[0156] Hence, SBS1, SBS3, and SBS4 can substitute the commonly used surfactants without loss of emulsion capacity.

[0157] Example 9 - Emulsion capacity of different chain lengths of SBS1

[0158] Emulsion capacity was measured by mixing 1 mL of 1 % surfactant solution in water with 1 mL sunflower oil for 20 seconds to form an emulsion. These were left at room temperature for 17 hours after which the emulsion phase was measured relative to the total volume.

[0159] SBS1 is, as described before, a glycolipid with a carbohydrate moiety being maltose and a lipid moiety being oleic acid (6- and / or 6'-oleyl-maltose). SBS5 is a mono-ester glycolipid with a carbohydrate moiety being maltose and a lipid moiety being palmitic acid (6- and / or 6'-palmityl-maltose). SBS6 is a mono-ester glycolipid with a carbohydrate moiety being maltose and a lipid moiety being myristic acid (6- and / or 6'-myristyl-maltose). SBS7 is a mono-ester glycolipid with a carbohydrate moiety being maltose and a lipid moiety being lauric acid (6- and / or 6'-lauryl-maltose).

[0160] The data show that SBS1 behaves very similar across the range of C12-C18 chain lengths in terms of emulsion capacity.

[0161] Example 10 - Personal cleaning product formulations with mono-ester glycolipids of different chain lengths

[0162] The following person cleaning product formulations were prepared. SBS1 is, as described before, a glycolipid with a carbohydrate moiety being maltose and a lipid moiety being oleic acid (6- and / or 6'-oleyl-maltose). SBS5 is a mono-ester glycolipid with a carbohydrate moiety being maltose and a lipid moiety being palmitic acid (6- and / or 6'- palmityl-maltose). SBS6 is a mono-ester glycolipid with a carbohydrate moiety being maltose and a lipid moiety being myristic acid (6- and / or 6'-myristyl-maltose). SBS7 is a mono-ester glycolipid with a carbohydrate moiety being maltose and a lipid moiety being lauric acid (6- and / or 6'-lauryl-maltose). SBS8 is a mono-ester glycolipid with a carbohydrate moiety being maltose and a lipid moiety being caprylic acid (6- and / or 6'- caprylyl-maltose).

[0163] Example 11 - Sulphate free hand soap

[0164] A hand soap without sulphates was formulated using SBS1. Ingredients are mixed in the listed order under stirring and lastly pH is adjusted to 5 with citric acid. Formulation

[0165] Example 12 - Conditioner A conditioner containing SBS1 was formulated. Ingredients in part 1 was mixed in the listed order until homogenous. Similarly, the ingredients in part 2 was mixed and afterwards added to part 1 under stirring. Finally, pH is adjusted to give the final formulation. Formulation

[0166] Example 13 - Cleansing wipes A solution for use in cleansing wipes was tested with SBS1. Ingredients are mixed in the listed order under stirring followed by adjusting pH to 5. The solution can finally be applied to a fabric used for cleansing wipes. Formulation

[0167] Example 14 - Shampoo bar

[0168] A shampoo bar containing SBS1 was formulated using the following ingredient list. The ingredients in part 1 are melted together at 70 degrees with the water and stirred until homogeneous. Ingredients of part 2 are mixed, heated to 70 degrees and stirred into part 1. The mixture is cooled to below 45 degrees and pH is adjusted to 5. Add the liquid to a desired mold and cool in a refrigerator until solid. Formulation

[0169] Example 15 - Cleansing face powder

[0170] A face powder formulation with SBS1 was made. All the ingredients are ground together to form a uniform powder. The powder works by dissolving in small amount of hot water and foaming up between the hands, generating a lather that can be applied to the face.

[0171] Formulation

Claims

Claims1. Use of a mono-ester glycolipid or a mixture of mono-ester glycolipids in personal cleaning products; wherein said mono-ester glycolipid or mixture of mono-ester glycolipids comprises an unmodified carbohydrate moiety.

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

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

4. The use according to claim 1, wherein the mono-ester glycolipid is either a 6-0-(lipid ester)-maltose, and / or a 6'-O-(l ipid ester)-maltose.

5. The use according to claim 4, wherein the 6-O-(lipid ester)-maltose and 6'-O-(lipid ester)-maltose is present in a molar ratio of 0.1-10, preferably 0.5-2, even more preferably 0.8-1.2 and most preferably 0.9-1.1.

6. The use according to any one of the claims 1-5, 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, palm oil, shea butter, shea butter oil, and mixtures thereof.

7. The use according to any one of the claims 1-6, 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.

8. The use according to any one of the claims 1-6, wherein said mono-ester glycolipid comprises a lipid moiety having a chain length is within the range of C8-C18, preferably within the range of C12-C18, most preferably within the range of C16-C18.

9. A personal cleaning product composition comprising :- water;- a moisturizer and / or conditioner; and- a mono-ester glycolipid or a mixture of mono-ester glycolipids; wherein said mono-esterglycolipid or mixture of mono-ester glycolipids comprises an unmodified carbohydrate moiety.

10. The personal cleaning product composition according to claim 9, wherein said monoester glycolipid or mixture of mono-ester glycolipids comprises an unmodified carbohydrate moiety selected from the group consisting of maltose, cellobiose, and trehalose.

11. The personal cleaning product composition according to claim 9, wherein said monoester glycolipid or mixture of mono-ester glycolipids comprises an unmodified carbohydrate moiety being maltose.

12. The personal cleaning product composition according to claim 9, wherein the monoester glycolipid is either a 6-0-(lipid ester)-maltose, and / or a 6'-0-(lipid ester)-maltose.

13. The personal surface cleaning product composition according to claim 12, wherein the 6-0-(lipid ester)-maltose and 6'-0-(lipid ester)-maltose is present in a molar ratio of 0.1- 10, preferably 0.5-2, even more preferably 0.8-1.2 and most preferably 0.9-1.1.

14. The personal cleaning product composition according to any one of the claims 9-13, 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, linseed oil, palm oil, shea butter, shea butter oil, and mixtures thereof, preferably derived from sunflower oil.

15. The personal cleaning product composition according to any one of the claims 9-14, 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 personal cleaning product composition according to any one of the claims 9-14, wherein said mono-ester glycolipid comprises a lipid moiety having a chain length is within the range of C8-C18, preferably within the range of C12-C18, most preferably within the range of C16-C18.

17. The personal cleaning product composition according to any one of the claims 9-16, wherein said moisturizer and / or conditioner is selected from glycerin, mineral oil, shea butter, cocoa butter, petrolatum, ceramides, hyaluronic acid, dimethicone, lanolin, jojobaoil, coconut oil, argan oil, squalane, panthenol, aloe vera, colloidal oatmeal, vitamin E, cetyl alcohol, stearyl alcohol, behentrimonium chloride, cetrimonium chloride, almond oil, avocado oil, olive oil, sunflower seed oil, glycolic acid, lactic acid, urea, sodium PCA, sorbitol, propylene glycol, caprylic / capric triglyceride, honey, beeswax, mango butter, rosehip oil, sweet almond oil, grapeseed oil, macadamia oil, hemp seed oil, evening primrose oil, borage oil, meadowfoam seed oil, marula oil, squalene, sodium lactate, linoleic acid, linolenic acid, allantoin, silk amino acids, hydrolyzed wheat protein, hydrolyzed soy protein, hydrolyzed keratin, elastin, collagen, snail mucin, beta-glucan, oat kernel oil, rice bran oil, babassu oil, tamanu oil, black seed oil, chia seed oil, pumpkin seed oil, pomegranate oil, sea buckthorn oil, monoi oil, kukui nut oil, murumuru butter, cupuacu butter, illipe butter, polyquaternium-7, polyquaternium-10, amodimethicone, cyclopentasiloxane, and mixtures thereof.

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