Use of mono-ester glycolipids in personal cleansing product compositions

Abstract

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

Description

Technical Field

[0001] This invention relates to emulsifiers for use in personal hygiene products. Background Technology

[0002] Personal care products, such as shampoos, shower gels, and facial cleansers, are typically composed of several basic ingredients. Each ingredient 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 product type, its intended use, and brand philosophy (e.g., natural, organic, hypoallergenic). The main basic ingredients are surfactants, water, moisturizers and conditioners, thickeners and stabilizers, pH adjusters, and emulsifiers. Other ingredients may include specific additives, preservatives, fragrances, and dyes. Surfactants are responsible for cleaning and forming lather. Lather is a foaming substance formed when surfactants are mixed with water and air (usually through agitation, such as rubbing or shaking). They lower surface tension, allowing the product to spread easily and trap dirt and oil. Water acts as a solvent, diluting other ingredients and facilitating their application and distribution. Moisturizers and conditioners help keep skin and hair hydrated, thus counteracting the potential drying effect of surfactants. Thickeners and stabilizers provide the desired consistency and stability for personal care products, 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 functions and chemical properties, are not always the same. They are typically selected from different types of chemicals based on their specific function in the product formulation. While the role of surfactants has been discussed above, emulsifiers are present to stabilize emulsions by reducing the surface tension between the oil and aqueous phases. Examples include anionic, cationic, and nonionic emulsifiers. Nonionic emulsifiers are generally preferred for products designed for sensitive skin due to their gentleness. Cationic emulsifiers are preferred for hair conditioners due to their conditioning properties. Anionic emulsifiers are typically selected for their ability to interact with dirt and oil, making them effective in cleansers and scrubs. Therefore, surfactants and emulsifiers can be chemically similar, and sometimes even the same compound can perform both functions. However, they are typically selected and used based on their primary function in the product—surfactants are used for cleaning and foaming, while emulsifiers are used to stabilize mixtures of oil and water.

[0003] One of the main concerns when formulating personal care products is their ability to form a lather, allowing the product to spread easily and trap dirt and oil. Currently used surfactants have shown great effectiveness. However, consumer demand for newer, gentler, and "more environmentally friendly" skin and hair care products means this area needs further investigation. Summary of the Invention

[0004] Therefore, the object of this invention is to provide an environmentally friendly alternative to the surfactants currently used to form soap foam.

[0005] The inventors of this invention have discovered the use of a new subtype of nonionic surfactant—monoester glycolipids—as an environmentally friendly alternative to conventional anionic and nonionic surfactants used in personal care products.

[0006] The inventors of this invention have also discovered a process for producing monoester glycolipids from renewable resources, such as enzymatically cleaved starch (e.g., maltose) and used edible oils (e.g., sunflower oil, rapeseed oil, corn oil, and olive oil). Furthermore, these monoester glycolipids are biodegradable. Some byproducts (glycerol and monoglycerides and diglycerides) can even be separated as valuable food ingredients or food additives, or retained with the monoester glycolipids for use as emulsifiers, humectants, and / or thickeners in personal care products.

[0007] Therefore, the first aspect relates to the use of monoester glycolipids or mixtures of monoester glycolipids in personal care products.

[0008] The second aspect relates to a personal care product composition comprising monoester glycolipids or mixtures of monoester glycolipids.

[0009] The third aspect relates to a personal hygiene product composition, said personal hygiene product composition comprising: - water; - Moisturizers and / or conditioning agents; and - Monoester glycolipids or mixtures of monoester glycolipids.

[0010] The fourth aspect relates to a process for producing a personal care product composition, the process comprising: (i) In a reaction vessel, the carbohydrates are dispersed and / or dissolved in a polar organic solvent; (ii) Add diglycerides and / or triglycerides to the reaction vessel to form a starting mixture; (iii) Disperse the lipase in the starting mixture under stirring; (iv) At a temperature between 0 and 100 degrees Celsius, the carbohydrate is subjected to transesterification with the diglyceride and / or triglyceride to form a first liquid fraction and a first solid fraction, the first liquid fraction comprising the polar organic solvent, monoglycerides, glycolipids, and monoglycerides, diglycerides, and / or triglycerides, and the first solid fraction comprising lipase and optionally unreacted carbohydrates. (v) Separating the first liquid fraction from the first solid fraction; (vi) Removing the polar organic solvent from the first liquid fraction to form a second liquid or solid fraction; and (vii) Add water and humectants and / or conditioning agents to the second liquid or solid fraction to form a personal care product composition.

[0011] Preferably, the monoester glycolipid or mixture of monoester glycolipids includes an unmodified carbohydrate portion.

[0012] Here, unmodified carbohydrates are defined as carbohydrates in their closed form, whose functionality other than anomeric acetal / hemiacetal consists only of hydroxyl groups, none of which are naturally or chemically replaced by other functional groups such as amino, alkoxy, carboxylic acid ester, or acetyl groups.

[0013] The invention will now be described in more detail below. Detailed Implementation

[0014] Glycolipids are amphiphilic nonionic molecules comprising a hydrophilic carbohydrate moiety and one or more fatty acids as lipophilic moieties. Monoester glycolipids have a single fatty acid as the lipophilic moiety. The inventors of this invention have discovered that monoester glycolipids possess properties comparable to or even better than those of conventional anionic and nonionic surfactants.

[0015] The main base components of personal care product compositions are surfactants, water, and moisturizers and conditioners. Other components may include thickeners and stabilizers, pH adjusters, emulsifiers, certain additives, preservatives, fragrances, and dyes.

[0016] As discussed in the Background section, surfactants are responsible for cleaning and forming soap foam. Soap foam is a foaming substance formed when surfactants are mixed with water and air (usually by agitation, such as rubbing or shaking). They reduce surface tension, allowing the product to spread easily and trap dirt and oil. A non-limiting list of surfactants commonly used in personal care products includes: sodium lauryl ether sulfate, sodium lauryl sulfate, cocamidopropyl betaine, ammonium lauryl ether sulfate, ammonium lauryl sulfate, sodium cocoyl ethoxysulfonate, sodium lauroyl sarcosinate, decyl glucoside, lauryl glucoside, sodium coamphoacetate, disodium lauryl ether sulfosuccinate, cocoyl glucoside, sodium cocoyl glutamate, sodium lauryl glucocarboxylate, lauryl hydroxysulfonate betaine, sodium methyl cocoyl taurate, octyl / decyl glucoside, and sodium methyl oleoyl taurate. Some of these are further discussed in the Examples section.

[0017] The surfactant content in personal care products can vary widely depending on the product type and its intended use. In products such as shampoos and shower gels, these typically contain relatively high concentrations of surfactants, ranging from 10% w / w to 20% w / w, or sometimes more. High surfactant content is necessary for effectively cleaning hair and body, removing oil, dirt, and other impurities. In facial cleansers, surfactant content can vary. Mild or sensitive skin formulations may have lower surfactant concentrations, approximately 5% w / w to 10% w / w. More potent cleansers designed for oily skin or deep cleansing may have higher levels, comparable to shampoos. While primarily formulated as conditioning agents, conditioners can also contain surfactants, but usually at lower concentrations compared to shampoos, such as approximately 1% w / w to 5% w / w, for emulsifying and stabilizing the product rather than for cleansing. In hand soaps and shower gels, the content can also vary, but is typically in the range of approximately 10% w / w to 15% w / w. The exact amount depends on the product's desired lather, cleansing power, and gentleness. Products designed for infants or those with sensitive skin typically have lower surfactant concentrations to minimize the risk of skin irritation. They may contain surfactants as low as approximately 1% w / w to 3% w / w.

[0018] Water acts as a solvent, diluting other ingredients and facilitating their application and distribution. The percentage of water in personal care products is influenced by the product's desired properties, such as viscosity, spreadability, and the concentration of active ingredients. Therefore, water not only acts as a solvent but also affects the product's texture and sensory feel. Typically, water content ranges from approximately 60% w / w to 90% w / w.

[0019] 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.

[0020] 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 include 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 make the hair smooth and protect it.

[0021] Moisturizers are used in both skincare and haircare products and are designed to increase the water content of the skin or hair. They work by drawing moisture from the environment (humectants, such as glycerin), sealing moisture into the skin or hair (occlusives, such as mineral oil), or restoring lipids in the skin (emollients, such as shea butter). 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 skincare, they can help restore the skin's barrier function, counteracting the potential drying effects of surfactants. The non-restricted list of moisturizers and conditioning agents commonly used in personal care products includes: glycerin, mineral oil, shea butter, cocoa butter, petrolatum, ceramides, hyaluronic acid, dimethicone, lanolin, jojoba oil, coconut oil, argan oil, squalane, panthenol, aloe vera, colloidal oat flour, vitamin E, cetyl alcohol, stearyl alcohol, behenyltrimethylammonium chloride, cetrimonium chloride, almond oil, avocado oil, olive oil, sunflower seed oil, glycolic acid, lactic acid, urea, sodium PCA, sorbitol, propylene glycol, caprylic / capric triglycerides, honey, beeswax, mango butter, rosehip oil, sweet almond oil, grapeseed oil, macadamia oil, evening primrose oil, borage oil, meadowfoam seed oil, and marula oil. Oil), squalene, sodium lactate, linoleic acid, linolenic acid, allantoin, silk amino acids, hydrolyzed wheat protein, hydrolyzed soybean 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, illipebutter, polyquaternium-7, polyquaternium-10, amino-terminated polydimethylsiloxane, cyclopentamethoxysiloxane.

[0022] Glycerin is widely used for its excellent humectant properties, drawing moisture into the skin and hair. Mineral oil is commonly found in a variety of cleansing products due to its ability to lock in moisture. Shea butter is valuable for its rich, moisturizing properties and is often used in higher-end formulations. Like shea butter, cocoa butter is known for its deep moisturizing and nourishing properties. Dimethicone is a silicone-based polymer used for its smoothing effect on skin and hair and as a protective barrier. Jojoba oil is similar to the skin's natural oils, making it an effective moisturizer. Coconut oil is popular for its nourishing properties and is often used in hair cleansing products. Argan oil is known for its restorative and nourishing properties, especially in hair cleansing products. Hyaluronic acid is highly effective as a humectant, attracting and retaining moisture in the skin. Cetyl alcohol and stearyl alcohol are fatty alcohols used to thicken and stabilize formulations, and also add moisturizing properties. Panthenol (provitamin B5) is commonly found in both skin and hair cleansing products for its moisturizing and softening properties. These ingredients are popular for their effectiveness in hydrating and conditioning 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 the desired effect in personal care products.

[0023] The levels of moisturizers and conditioners in personal care products can vary widely depending on the product type and its specific formulation. Shampoos typically contain lower concentrations of moisturizers and conditioners, ranging from 1% w / w to 5% w / w. Some moisturizing or repairing shampoos may have slightly higher amounts. Conditioners and hair masks generally have higher concentrations of moisturizers and conditioners, typically between 5% w / w and 20% w / w, depending on the product's intended effect (e.g., smoothing, conditioning, or deep conditioning). Shower gels and body washes are generally lower than conditioners, ranging from 1% w / w to 5% w / w. Products marketed for dry skin may contain higher levels. Facial cleansers typically contain approximately 1% w / w to 3% w / w, as their primary purpose is cleansing. Formulations for dry or sensitive skin may have slightly higher levels of moisturizers to reduce potential dryness after cleansing. Similar to shower gels, hand soaps contain lower amounts of moisturizers, typically between 1% w / w and 3% w / w. However, some hand soaps designed for dry skin may have an increased content of moisturizers.

[0024] The first aspect relates to the use of monoester glycolipids or mixtures of monoester glycolipids in personal care products. Preferably, the monoester glycolipids or mixtures of monoester glycolipids comprise an unmodified carbohydrate portion.

[0025] The second aspect relates to a personal care product composition comprising monoester glycolipids or mixtures of monoester glycolipids. Preferably, the monoester glycolipids or mixtures of monoester glycolipids comprise an unmodified carbohydrate portion.

[0026] The third aspect relates to a personal hygiene product composition, said personal hygiene product composition comprising: - water; - Moisturizers and / or conditioning agents; and - Monoester glycolipids or mixtures of monoester glycolipids.

[0027] The fourth aspect relates to a personal hygiene product composition, said personal hygiene product composition comprising: - 60% w / w to 90% w / w of water; - 1% w / w to 5% w / w moisturizers and / or conditioning agents; and - 1% w / w to 30% w / w monoester glycolipids or mixtures of monoester glycolipids.

[0028] In one or more embodiments, the moisturizer and / or conditioning agent is selected from: glycerin, mineral oil, shea butter, cocoa butter, petrolatum, ceramide, hyaluronic acid, dimethicone, lanolin, jojoba oil, coconut oil, argan oil, squalane, panthenol, aloe vera, colloidal oat flour, vitamin E, cetyl alcohol, stearyl alcohol, behenyltrimethylammonium chloride, cetrimonium chloride, almond oil, avocado oil, olive oil, sunflower seed oil, glycolic acid, lactic acid, urea, sodium PCA, sorbitol, propylene glycol, caprylic / capric triglycerides, honey, beeswax, mango butter, rosehip oil, sweet almond oil, grapeseed oil, macadamia nut 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 soybean protein, hydrolyzed keratin, elastin, collagen, snail mucus, beta-glucan, oat kernel oil, rice bran oil, babassu seed oil, tamanu oil, black seed oil, chia seed oil, pumpkin seed oil, pomegranate oil, sea buckthorn oil, monoi oil, kukui nut oil, murumol palm oil, gupuasau fruit oil, Indian hematite fruit fat, polyquaternium-7, polyquaternium-10, amino-terminated polydimethylsiloxane, cyclopentamethoxysiloxane and mixtures thereof.

[0029] The inventors of this invention have also discovered a process for producing monoester glycolipids from renewable resources.

[0030] The personal hygiene product composition of the present invention can take any of a variety of forms. It can take the following forms: shampoo, conditioner, shower gel, facial cleanser, hand soap, bath gel, bubble bath, exfoliating scrub, facial toner, micellar water, makeup remover, dandruff treatment, bar soap, bath oil, feminine wash, or any other personal hygiene product composition known to those skilled in the art.

[0031] In one or more embodiments, monoester glycolipids or mixtures of monoester glycolipids include carbohydrate portions selected from polysaccharides such as starch, for example monosaccharides and / or disaccharides obtained by enzymatic cleavage.

[0032] In one or more embodiments, the monoester glycolipid or mixture of monoester glycolipids comprises a carbohydrate portion selected from the group consisting of maltose, sucrose, lactose, cellobiose, trehalose, isomaltulose, lactulose, and isomaltose.

[0033] In one or more embodiments, the monoester glycolipid or mixture of monoester glycolipids comprises a carbohydrate portion selected from the group consisting of glucose, fructose, galactose, mannose, fucose, xylose, ribose, N-acetylglucosamine, N-acetylneuraminic acid, arabinose, glucuronic acid, guluronic acid, mannuronic acid, and sialic acid.

[0034] In one or more embodiments, the monoester glycolipid or mixture of monoester glycolipids comprises a carbohydrate portion selected from the group consisting of maltose, cellobiose and trehalose, preferably unmodified.

[0035] In one or more embodiments, the monoester glycolipid or mixture of monoester glycolipids includes a carbohydrate portion (preferably unmodified) that is maltose.

[0036] In one or more embodiments, the monoester glycolipid is 6-O-(lipid ester)-maltose, and / or 6'-O-(lipid ester)-maltose.

[0037] Preferably, 6-O-(lipid ester)-maltose and 6'-O-(lipid ester)-maltose are 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.

[0038] The performance of a surfactant depends on the balance between the hydrophilicity of the head group and the hydrophobicity of the tail group. In the case of monoester glycolipids, this corresponds to the hydrophilicity of the carbohydrate moiety and the hydrophobicity of the hydrocarbon moiety. In the case of disaccharides, the solubility (and therefore hydrophilicity) in water can differ by up to an order of magnitude (as seen in the table below, e.g., sucrose versus cellobiose). This makes it difficult to predict whether surfactants made from these different disaccharides will exhibit similar properties and whether they are suitable as surfactants in laundry detergents. Furthermore, the table shows how the solubility changes significantly (approximately 8-fold) when comparing glucose and methyl glucoside (glucose methylated at position 1). This demonstrates that the properties of surfactants made from unmodified carbohydrates are difficult to predict in advance compared to modified glycosylated carbohydrates.

[0039]

[0040] In addition to solubility, it was found that the self-assembly of micelle structures is highly dependent on the isomer structures of specific molecules. 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) This demonstrates that α or β configurations of glycosidic bonds significantly alter micellar structure. Furthermore, it shows significant changes in the micellar structure between maltose and lactose-based APGs due to the H-bonding patterns between carbohydrates and between carbohydrates and water. The latter is related to water solubility. Self-assembly and micellar structure are important for personal care products because larger, elongated micelles produce a thickening effect, while smaller, spherical micelles create a free-flowing solution. Macroscopic variations (e.g., feel, texture, viscosity) are highly valuable to consumers' experience with these personal care products, such as shampoos, micellar waters, or hand soaps. Due to these complex H-bonding patterns between carbohydrates in solution and between carbohydrates and water, it is difficult, even for experts in the field, to predict the self-assembly behavior of two surfactants with the same molecular structure but different isomer compositions.

[0041] In one or more embodiments, the monoester glycolipid comprises a lipid portion derived from diglycerides and / or triglycerides selected from the following sources: sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, tallow, lard, rice bran oil, coconut oil, flaxseed oil, palm oil, shea butter, shea butter, 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; therefore, the lipid portion will primarily be one of these four fatty acids.

[0042] In one or more embodiments, the monoester glycolipid includes a lipid portion derived from oleic acid and / or linoleic acid.

[0043] In one or more embodiments, the monoester glycolipid comprises a lipid moiety having a chain length in the range of C6-C26, which is either saturated or unsaturated with 1-6 double bonds. Preferably, the chain length is in the range of C8-C18. More preferably, the chain length is in the range of C12-C18. Even more preferably, the chain length is in the range of C16-C18.

[0044] Preferably, the lipid portion is derived from oleic acid and / or linoleic acid and / or stearic acid and / or palmitic acid and / or trans-palmitooleic acid and / or palmitoleic acid.

[0045] In one or more embodiments, the monoester glycolipid or mixture of monoester glycolipids includes a carbohydrate portion, said carbohydrate portion being maltose.

[0046] In one or more embodiments, the monoglyceride glycolipid or mixture of monoglycerides includes a carbohydrate portion, said carbohydrate portion being maltose, and wherein said monoglyceride glycolipid includes a lipid portion derived from diglycerides and / or triglycerides selected from sunflower seed oil.

[0047] In one or more embodiments, the monoglyceride glycolipid or mixture of monoglycerides includes a carbohydrate portion, which is maltose, and wherein the monoglyceride glycolipid includes a lipid portion derived from diglycerides and / or triglycerides selected from sources including: sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, tallow, lard, rice bran oil, coconut oil, flaxseed oil, palm oil, shea butter, shea butter, and mixtures thereof, preferably derived from sunflower oil.

[0048] As used herein, the term "carbohydrate" refers to monosaccharides and oligosaccharides. It also includes derivatives of these compounds. As used herein, the term "carbohydrate" does not include starch, cellulose, and guar gum, or other polysaccharides having a high weight-average molecular weight. As defined in this application, "high weight-average molecular weight" refers to those exceeding about 3000 Daltons. As used herein, the term "oligosaccharide" refers to a chain of two or more sugars linked by glycosidic bonds, with a weight-average molecular weight of less than about 3000 Daltons. Preferably, carbohydrates are monosaccharides or disaccharides. Preferred disaccharides may be, for example, maltose, sucrose, lactose, cellobiose, trehalose, and isomaltose. Preferred monosaccharides may be, for example, glucose, fructose, galactose, mannose, fucose, xylose, glucuronic acid, guluronic acid, mannuronic acid, and ribose. Preferably, the monosaccharides and / or disaccharides are derived from polysaccharides, such as starch, for example, through enzymatic cleavage. The inventors of this invention have discovered that, possibly due to steric hindrance, using the specific method described in Example 1, when the carbohydrate is glucose, only the C6-ol reacts with the fatty acid, while when the carbohydrate is maltose, either the C6-ol or the C6'-ol reacts with the fatty acid.

[0049] 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.

[0050] In one or more embodiments, the carbohydrate is a disaccharide.

[0051] In one or more embodiments, the carbohydrate is selected from the group consisting of glucose, fructose, galactose, mannose, fucose, xylose, ribose, N-acetylglucosamine, N-acetylneuraminic acid, arabinose, sialic acid, glucuronic acid, guluronic acid, mannuronic acid, and mixtures thereof.

[0052] In one or more embodiments, the carbohydrate is a monosaccharide.

[0053] The process for producing monoester glycolipids can be as follows: (i) In a reaction vessel, the carbohydrates are dispersed and / or dissolved in a polar organic solvent; (ii) Add diglycerides and / or triglycerides to the reaction vessel to form a starting mixture; (iii) Disperse the lipase in the starting mixture under stirring; (iv) At a temperature between 0 and 100 degrees Celsius, the carbohydrate is subjected to transesterification with the diglyceride and / or triglyceride to form a first liquid fraction and a first solid fraction, the first liquid fraction comprising the polar organic solvent, monoglycerides, glycolipids, and monoglycerides, diglycerides, and / or triglycerides, and the first solid fraction comprising lipase and optionally unreacted carbohydrates. (v) separating the first liquid fraction from the first solid fraction; and (vi) Separating the monoglyceride glycolipid from the first liquid fraction to form a second liquid fraction, the second liquid fraction comprising monoglycerides, diglycerides and / or triglycerides.

[0054] The concept involves using lipases to catalyze transesterification between carbohydrates and diglycerides and / or triglycerides to form monoglyceride glycolipids and glycerides with one less fatty acid bound to them (i.e., monoglycerides or diglycerides, respectively). Depending on the type of lipase, diglycerides (diacylglycerols) can act as substrates to undergo a new reaction with another carbohydrate molecule to form monoglyceride glycolipids and monoglycerides. Similarly, depending on the lipase used, monoglycerides (monoacylglycerols) can act as substrates to undergo a new reaction with another carbohydrate molecule to form monoglyceride glycolipids and glycerol. The different reaction products (glycerol and / or monoglycerides and / or diglycerides) can be retained with the produced monoglyceride glycolipids, as in the subsequently produced personal care product compositions, as illustrated in the process described below.

[0055] The fifth aspect relates to a process for producing a personal care product composition, the process comprising: (i) In a reaction vessel, the carbohydrates are dispersed and / or dissolved in a polar organic solvent; (ii) Add diglycerides and / or triglycerides to the reaction vessel to form a starting mixture; (iii) Disperse the lipase in the starting mixture under stirring; (iv) At a temperature between 0 and 100 degrees Celsius, the carbohydrate is subjected to transesterification with the diglyceride and / or triglyceride to form a first liquid fraction and a first solid fraction, the first liquid fraction comprising the polar organic solvent, monoglycerides, glycolipids, and monoglycerides, diglycerides, and / or triglycerides, and the first solid fraction comprising lipase and optionally unreacted carbohydrates. (v) Separating the first liquid fraction from the first solid fraction; (vi) Removing the polar organic solvent from the first liquid fraction to form a second liquid or solid fraction; and (vii) Add water and humectants and / or conditioning agents to the second liquid or solid fraction to form a personal care product composition.

[0056] In this context, the term "ester exchange" refers to a chemical reaction in which, in the presence of a catalyst (i.e., a lipase), the alkoxy group of an ester compound, namely diglycerides and / or triglycerides (and optionally subsequently formed monoglycerides), is exchanged with another alkoxy group through the reaction of the ester with an alcohol (i.e., a carbohydrate).

[0057] As used herein, the term "glyceride" (also known as acylglycerol) refers to monoglycerides, diglycerides, triglycerides, or combinations thereof. These are esters formed from glycerol and fatty acids. Glycerides in oils may include a variety of fatty acids, both saturated and unsaturated. As used herein, the term "triglyceride" refers to an ester derived from glycerol and three fatty acids. The triglycerides of this disclosure may be saturated or unsaturated. Similarly, the term "diglyceride" refers to an ester derived from glycerol and two fatty acids, while the term "monoglyceride" refers to an ester derived from glycerol and one fatty acid.

[0058] Preferably, the triglyceride source is selected from sources consisting of: sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, tallow, lard, rice bran oil, coconut oil, flaxseed oil, palm oil, shea butter, shea butter, and mixtures thereof.

[0059] As used herein, the term "fatty acid" refers to molecules derived from triglycerides and includes carboxylic acids with long aliphatic tails (chains), which may be saturated or unsaturated. When not attached to other molecules, they are called "free" fatty acids. Most naturally occurring fatty acids have chains with an even number of carbon atoms, ranging from 4 to 28. Short-chain fatty acids (SCFAs) are fatty acids with aliphatic tails of fewer than six carbons. Medium-chain fatty acids (MCFAs) are fatty acids with aliphatic tails of 6–12 carbons, which can form medium-chain triglycerides. Long-chain fatty acids (LCFAs) are fatty acids with aliphatic tails of 13 to 21 carbons. Very long-chain fatty acids (VLCFAs) are fatty acids with aliphatic tails longer than 22 carbons. In one instance, a fatty acid or its ester may include at least 10, at least 12, at least 14, at least 16, at least 18, or at least 20 carbon atoms. In some specific instances, the fatty acid or its ester may comprise 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, or 45 carbon atoms, wherein any of these values ​​may, where appropriate, form upper or lower limit endpoints. In other instances, the glycerol ester may comprise a mixture of fatty acids or their esters with different chain length ranges.

[0060] Because each lipase exhibits different fatty acid specificities (both saturated / unsaturated specificity and 1,3 specificity), it is important to select the appropriate lipase based on the type of fatty acids in the glycerol ester. If non-regional specificity (i.e., the ability to cleave / transfer all fatty acids from the glycerol ester) is required, then a lipase with non-regional specificity should be selected. A suitable example could be, for instance, *Candida antarcticis* (…). Candida antarctica Type B lipase and lipase OF (derived from Candida albicans) Candida rugosa )), lipase G (derived from Penicillium carmenensis) Penicillium camembertii ), lipase AYS (from Candida albicans), lipase PS (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 javanica ( Mucor javanicus If region specificity is required (i.e., only certain fatty acids can be cleaved / transferred from glycerides), then a region-specific lipase should be selected. A suitable example of 1,3-region specificity could be, for example, lipase F-AP15 (derived from Rhizopus oryzae). Rhizopus oryzae)), lipase Newlase F3G (derived from Rhizopus spp.) Rhizopus niveus )), lipase R (derived from Rockefeller penicillin ( Penicillium roqueforti Lipozyme RM-IM (derived from Rhizopus micranthum) Rhizomucor miehei Lipozyme TL-IM (derived from the cottony thermophilic mold) Thermomyces lanuginosus And pancreatic lipase (derived from pig pancreas).

[0061] In one or more embodiments, the lipase is selective for position 1, position 3, or both of the glycerol ester.

[0062] In one or more embodiments, the lipase selective for position 1, position 3, or both is selected from: *Chlorophyllum molybdites* (…). Chromobacterium viscosum ), canine gastric lipase, canine pancreatic lipase, Fusarium solani ( Fusarium solani ) Keratinase lipase, guinea pig pancreatic lipase, human gastric lipase, cottony humic mold ( Humicola lanuginosus Lipase, human pancreatic lipase, lipoprotein lipase, and Mucor mitochondritis ( Mucor miehei Lipase, Pseudomonas aeruginosa Pseudomonas aeruginosa Lipase, Penicillium carmenensis ( Penicillium camemberti Lipase, Fluorescent Pseudomonas ( Pseudomonas fluorescens Lipase, Pseudomonas laminarinus ( Pseudomonas glumae Lipase, porcine pancreatic lipase, Penicillium spp. Penicillium simplicissimum Lipase, Rhizopus oligosporus ( Rhizopus arrhizus Lipase, rabbit gastric lipase, Fusarium heterospora ( Fusarium heterosporum Lipase, Candida lipase and its variants.

[0063] In one or more embodiments, the lipase is non-selective for position in the glycerol ester.

[0064] In one or more embodiments, the process further includes the step of separating monoglycerides, diglycerides, and / or triglycerides from the second liquid fraction.

[0065] Monoglycerides are used as emulsifiers in a variety of foods, such as whipped cream, baked goods, and ice cream. Diglycerides are common food additives used to blend certain ingredients, such as oils and water. Furthermore, both monoglycerides and diglycerides are recommended as shortening and shelf-life extenders in baked margarine and shortening. They are also used as shortening agents in ice cream and imitation cream. While their role as emulsifiers is more commonly associated with food products, monoglycerides can also function in personal care products. Monoglycerides can act as emulsifiers, helping to blend and stabilize mixtures of oils and water in products. Like other fatty acid derivatives, monoglycerides can also have conditioning effects on the skin. They can contribute to the overall texture and viscosity of a product, enhancing its application and feel on skin or hair. Glycerin has been described as a commonly used moisturizer in personal care product compositions. Therefore, different reaction products (glycerin and / or monoglycerides and / or diglycerides) can be retained in subsequently produced personal care product compositions along with the produced monoglyceride glycolipids.

[0066] It is anticipated that the aforementioned lipase specificity (saturated / unsaturated specificity and 1,3-position specificity) will be high at low conversion rates, and will decrease as preferred substrates are consumed and less preferred substrates are simultaneously added. Therefore, it is preferable to carry out the reaction at low conversion rates to ensure the highest possible specificity. In some embodiments of the invention, it is advantageous to fully utilize all reaction products even at low transesterification conversion rates.

[0067] In one or more embodiments, the present invention relates to a process in which the transesterification conversion to monoglycerides and monoglycerides or diglycerides is less than 5%, less than 10%, less than 15%, less than 20%, less than 25%, less than 30%, less than 35%, less than 40%, less than 45%, or less than 50%.

[0068] In one or more embodiments, the present invention relates to a process in which the transesterification of monoglycerides and monoglycerides or diglycerides is at a conversion rate of at least 40%, at least 45%, at least 50%, at least 55%, at least 60%, at least 65%, or at least 70%.

[0069] In one or more embodiments, the present invention relates to a process in which the lipase is selective for saturated fatty acids, preferably selected from Candida antarcticis lipase A and Fusarium oxysporum (…). Fusarium oxysporum Lipases and their variants.

[0070] The separation method for purifying monoglycerides or diglycerides from the first liquid fraction may be selected from deodorization, distillation, evaporation, or any combination thereof. The presence of fatty acid esters or free fatty acids may be removed as a volatile fraction by deodorization, evaporation, or distillation. This volatile fraction may be further separated into alcohols (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, as is well known in the art. The deodorizer may be operated at 0.15 mbar, 225 °C, with a steam consumption of 0.20% to 0.25% w / w per hour. Other operating modes are known in the art, for example, see 'Introduction to Fats and Oil Technology', Eds O'Brien, Farrr and Wan, AOCS Publishing, Chapter 13, 2000.

[0071] Methods of distillation and evaporation are also known in the art. Evaporation units for oils are typically steam distillation units, referred to as deodorizers. For step (VIII), high-vacuum distillation is one implementation method to minimize thermal damage. In some embodiments of the invention, a system with multiple equilibration stages is preferred to achieve good separation. Other preferred embodiments include falling film molecular distillers operating at pressures of 0.001 to 10 mmHg and temperatures of 140–200 degrees Celsius, or centrifugal molecular distillers that can operate at pressures of approximately 0.001–10 mmHg and temperatures of 160–240 degrees Celsius (both modes are described in detail in Batistella et al., Appl. Biotechn., vol. 98, 1149–1159, 2002). Direct or indirect heating can be used, and the operation can be carried out in batches and / or continuously.

[0072] Preferably, the transesterification can be carried out at a temperature in the range of 20-95 degrees Celsius, depending on the optimal conditions for the lipase to function, such as in the range of 30-85 degrees Celsius, for example in the range of 40-75 degrees Celsius, such as in the range of 50-65 degrees Celsius, for example at about 60 degrees Celsius.

[0073] The time period for transesterification is preferably in the range of several minutes, such as five minutes, to several hours, such as 120 hours, depending on the reaction time of the reactants used.

[0074] The preferred solvents for transesterification reactions are: tert-amyl alcohol, acetone, tert-butanol, 1-propanol, isopropanol, isobutanol, and isoamyl alcohol.

[0075] The resulting glycolipids can be purified using standard methods, such as extraction, filtration through mesoporous adsorbents or filters, chromatography using various solvents based on affinity or adsorption, distillation of any remaining volatile solvents, and centrifugation to separate precipitates, byproducts, or reactants. Suitable solvents for chromatography include, for example, water, methanol, ethyl acetate, ethanol, pentane, hexane, heptane, acetone, methyl ethyl ketone, dichloromethane, tert-amyl alcohol, and 1-propanol.

[0076] The disclosed method for producing monoester glycolipids is an exemplary, but preferred, method. Other methods are also covered in this invention.

[0077] It should be noted that the embodiments and features described in the context of one aspect of the invention are also applicable to other aspects of the invention.

[0078] Example Example 1 - Production of monoester glycolipids Monosaccharides or disaccharides were added to a stirred tank with a selected solvent to prepare a 10% w / w dispersion. Oil was then added under stirring to achieve a 1:1 molar ratio of oil to sugar. Lipase was added at a concentration of 10 WT% (relative to sugar mass). The reaction mixture was heated to 60°C and stirred for 120 hours. Product formation was detected by TLC analysis and subsequently purified by column chromatography using elution with DCM:MeOH.

[0079] Examples of solvents tested and used: tert-amyl alcohol, acetone, tert-butanol, 1-propanol, isopropanol, isobutanol, and isoamyl alcohol.

[0080] Examples of lipases tested and used: Candida antarcticis type B lipase, Lipozyme RM-IM (derived from Rhizopus miltiorrhiza), and Lipozyme TL-IM (derived from Thermophilus sparsely cottony).

[0081] Monoester glycolipids have been synthesized based on maltose, sucrose, cellobiose, trehalose, galactose, glucose, fructose, and isomaltose. Another reactant is selected from sunflower oil, rapeseed oil, olive oil, frying oil (i.e., a mixture of sunflower oil, rapeseed oil, and corn oil), and shea butter. Experiments were unsuccessful when xylose and lactose were used as carbohydrates.

[0082] Example 2 - Comparative Personal Care Product Compositions A series of five personal care product compositions were formulated (see Table 1 below), with only one component differing from each other. All five personal care product compositions include sodium lauryl ether sulfate (SLES). SLES is a widely used surfactant in personal care and cleaning products. SLES is primarily used for its detergent properties. It helps remove dirt, oil, and other impurities from skin, hair, and other surfaces. It is also responsible for producing lather in products such as shampoos, shower gels, and facial cleansers. Lather helps distribute the product evenly and makes the cleaning process more effective and pleasant for the user. SLES also helps mix water with oil and dirt, allowing them to be rinsed away. This makes it effective in products that require the removal of oily substances from skin or hair. Despite its widespread use, SLES has been under scrutiny. It is generally considered less irritating than its close relative, sodium lauryl sulfate (SLS), because it acts more gently on the skin and hair. However, concerns remain regarding potential irritation in high concentrations or in sensitive individuals, as well as environmental impacts. This has led to the development of SLES alternatives in some natural or organic personal care products. Of the five compositions, the control had the highest concentration of SLES; however, in compositions #1-#4, half of the SLES was replaced by other surfactants. Composition #1 was prepared with a monoester glycolipid (SBS1), while three different commercial surfactants (octyl / decyl glucoside, cocoyl glucoside, and rhamnolipid) were selected for testing against SBS1. SBS1 is a monoester glycolipid with a carbohydrate moiety of maltose and a lipid moiety of oleic acid (6- and / or 6'-oleoyl-maltose). Octyl / decyl glucoside is a nonionic surfactant used in cosmetic and personal care formulations, including lotions and creams. It is considered a mild and non-irritating emulsifier suitable for sensitive skin. Due to its gentle cleansing and foaming properties, it is commonly found in facial cleansers, shampoos, and shower gels, especially in products marketed for sensitive skin or natural cosmetics. Cocoyl glucoside is another nonionic surfactant widely used in personal care and cosmetic formulations. Derived from coconut oil and glucose, it is a natural and biodegradable ingredient. Coco-glucosides are valuable for their gentle cleansing properties and compatibility with all skin types, making them a key component in formulations for sensitive or delicate skin. They are commonly found in baby shampoos, sensitive skin formulations, and natural products. Rhamnolipids are a class of anionic surfactants (pKa approximately 5.5) that are produced by microorganisms, particularly bacteria of the genus *Pseudomonas*. They consist of rhamnose (a naturally occurring sugar) and 3-(hydroxyalkyloxy)alkyl acids (HAA) fatty acids (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 cosmetics industry.

[0083] In addition to surfactants and water (which, for example, act as solvents and hydrating agents), the composition also includes glycerin (glycerol), sodium chloride, citric acid / sodium hydroxide, and potassium sorbate. Glycerin is an excellent humectant. When applied to the skin, it draws moisture from the environment and the lower layers of the skin to the outer layers, keeping the skin hydrated and supple. In hair care products, it helps maintain hair moisture, reducing dryness and frizz. Glycerin also acts as a preservative. Sodium chloride is used to adjust the viscosity of products such as shampoos and shower gels. 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 effectively inhibits the growth of molds, yeasts, and some bacteria. By preventing microbial growth, it extends the product's shelf life and maintains its safety and quality.

[0084] Table 1

[0085] Test methods and results Foaming ability The foaming properties of personal care products (such as shampoos, face washes, and conditioners) are an important aspect of their functionality and consumer appeal. Foam helps to distribute cleansers evenly on the skin or hair. The lather produced by foam effectively traps dirt, oil, and other impurities, making them easier to rinse off. Consumers often associate the amount of foam with the product's cleaning power. More foam gives the psychological impression of a better and more thorough clean. Foam enhances the sensory experience of using the product. It can make the cleaning process feel more comfortable and pleasant, contributing to overall user satisfaction.

[0086] The test was conducted as follows: 50 mL of the personal care product composition to be tested (control, or one of compositions #1-#4) was added to a 500 mL graduated cylinder with a diameter of 48 mm. 200 mL of the same personal care product composition was added to a reservoir (500 mL separatory funnel) and placed above the graduated cylinder, with the tip of the funnel 80 cm above the solution surface. The funnel was opened, and timing began when the solution had flowed from the reservoir. The height of the foam was then measured at set time intervals of 60 s (th1), 180 s (th2), and 300 s (th3). All tests were performed in triplicate, and the surfactant concentration used in the experiments was 0.1%. The results are shown in Table 2 below.

[0087] Table 2

[0088] Foaming tests showed that the control formulation produced the most foam. However, when comparing all formulations, only small differences in foaming height and stability were observed. This suggests that SBS1(#1) can be used in personal care product compositions without disrupting foaming ability and that it can be used to at least partially replace SLES.

[0089] Viscosity 4 mL of the tested formulation was allowed to flow by gravity alone through an orifice (13 mm in length and Ø 2.4 mm). The outflow time of the sample was measured and used as an indicator of the formulation's viscosity; i.e., the longer the flow time, the higher the viscosity. Two reference fluids (water and commercial shampoo) were included in the test setup. The test was conducted at room temperature (22°C). The results are shown in Table 3. Surprisingly, SBS1 (#1) also appears to have a role as a thickener (viscosity-building component), which is suitable for compositions that do not require additional thickeners, thus avoiding thickeners such as sodium chloride, xanthan gum, carbomer, and cellulose derivatives.

[0090] Table 3

[0091] emulsification The emulsifying ability of the formulation was measured by mixing it with paraffin oil and measuring the height of the emulsion. For each test, 5 mL of the formulation (diluted with water to approximately 1:1000 to 0.01% of the total surfactant concentration) and 5 mL of low-viscosity paraffin oil were used. The test was performed in triplicate. The mixture was vortexed for 10 seconds and allowed to stand. After 10 minutes and 1 hour, the ratio between the height of the emulsion and the total volume height was measured.

[0092] The same commercially available surfactants as described above were used as the baseline. In addition to SBS1, two other surfactants, SBS2 and SBS3, were also tested. As previously described, SBS1 is a glycolipid with maltose as its carbohydrate moiety and oleic acid (6- and / or 6'-oleoyl-maltose) as its lipid moiety. SBS2 is a monoester glycolipid with sucrose as its carbohydrate moiety and oleic acid (6- and / or 6'-oleoyl-sucrose) as its lipid moiety. SBS3 is a monoester glycolipid with trehalose as its carbohydrate moiety and oleic acid (6- and / or 6'-oleoyl-trehalose) as its lipid moiety. The results are shown in Table 4.

[0093] Table 4

[0094] Emulsification data show that the capabilities of all compositions / formulations are similar after both 10 minutes and 1 hour.

[0095] Therefore, SBS1-3 appears to be a reasonable alternative to commonly used surfactants, without even sacrificing emulsifying ability.

[0096] Example 3 - Shampoo The sensory properties of the foam generated during washing were tested. A 2.5 cm x 20 cm hair tress was wetted with water, and 1 mL of shampoo formulation was placed on it. Foaming was achieved by agitation between the hands, and the results were evaluated sensorily and visually. In this example, SBS1 was compared with sucrose ester emulsifiers, cocoyl glucoside, rhamnolipid, and cetearyl glycoside / cetearyl alcohol. SBS1 has shown to be milder than other surfactants in terms of eye irritation, as it is the only surfactant that is non-irritating to the eyes. For SBS1, this was investigated through in vitro studies following OECD TG 492B guidelines.

[0097] preparation

[0098] result

[0099] For formulations #1, #4, and #5, the shampoo provides a nice, rich lather.

[0100] Example 4 - Shampoo without thickener A formulation similar to that used in evaluating the foam in Example 3 was used, but the thickener sodium chloride was replaced with the same amount of glycolipid. Sodium chloride is commonly used as a thickener in commercial shampoo formulations to achieve an acceptable viscosity for the product. Salt can cause product buildup over time, reducing shampoo effectiveness as it alters texture and consistency. Sodium chloride can be particularly harmful to dyed hair because it opens the cuticle, causing the color to fade more quickly and reducing the overall vibrancy of the hair. In this example, SBS1 was compared with sucrose ester emulsifiers, cocoyl glucoside, rhamnolipid, and cetearyl glycoside / cetearyl alcohol.

[0101] preparation

[0102] result

[0103] For formulations #1 and #2 only, good viscosity comparable to commercial shampoos can be obtained without the use of sodium chloride. This demonstrates that SBS1 can be used as a bio-based thickener.

[0104] Example 5 - Facial Cleanser The ability of SBS1 to function in a facial cleanser was tested by removing waterproof mascara from the skin. Waterproof mascara stains were applied to the skin and allowed to dry, then the stains were attempted to be removed with a facial cleanser. SBS1 was tested at different concentrations (1.0, 0.5, and 0.2% Wt. % active ingredient).

[0105] preparation

[0106] result

[0107] For all tested formulations, even as low as 0.2% Wt. % active ingredient, SBS1 was able to remove waterproof mascara stains.

[0108] Example 6 - Shower Gel without Thickener Similar to the shampoo test without thickeners, this test examined the shower gel formulation without the addition of any common thickeners such as sodium chloride and xanthan gum. In commercial shower gels, sodium chloride or xanthan gum is commonly used to achieve an acceptable viscosity.

[0109] preparation

[0110] result When formulated, only #1 yields a commercially viable consistency, while #2 and #3 result in a water-like consistency similar to shower gel. This demonstrates that SBS1 can be used as a bio-based thickener.

[0111] Example 7 - Comparison of maltose monoesters with different isomer compositions Maltose monoesters were prepared according to the method described in US5550225A, wherein the isomer composition was listed as at least 70 percent of a 6'-position monoester and the remainder as a 1-position monoester (glycosyl ester). The reaction was carried out in an organic solvent medium using a mixture of carboxylic anhydride and carbonic anhydride. The SBS1 presented in this patent was produced by an enzyme (more specifically, a lipase) to yield a mixture of 6' and 6' monoesters. Both products were purified by rapid column chromatography prior to analytical and application testing.

[0112] The two products showed the same retention factor on silica gel thin-layer chromatography with WIPE (1:2:9) eluent, but showed different isomer compositions on HPLC, in which the isomers could be separated.

[0113] result Visually, maltose monoester produced by the method described in US5550225A is opaque in a 1 mg / mL solution, while SBS1 is clear.

[0114] The ability of both products to dissolve oil droplets was studied.

[0115] For this test, 4 mL of 0.01% maltose monoester sample was mixed with 4 mL of sunflower seed oil by vortexing for 20 seconds. The emulsion was allowed to stand for 10 min, and the aqueous phase sample was removed with a syringe and measured at 660 nm on UV-vis. The test was performed in triplicate. Turbidity was measured 10 min after mixing.

[0116] Water was used as the blank. As a negative control, the aqueous phase of a mixture of deionized water and sunflower seed oil was measured.

[0117]

[0118] This clearly demonstrates that SBS1 dissolves oil droplets much better in the aqueous phase. These measurements are supplemented by optical microscopy images showing a significantly greater variety of emulsion droplets of different sizes for SBS1 compared to maltose monoester from US5550225A. These data clearly demonstrate that, despite having the same molecular formula, surfactant properties are highly dependent on the isomer composition.

[0119] Example 8 - Emulsifying ability of different carbohydrate fractions of SBS1 The emulsifying ability of different surfactants was tested. For each test, 2 mL of water containing 0.01% surfactant and 2 mL of sunflower oil were used. Tests were performed in triplicate. The mixture was vortexed for 20 seconds and allowed to stand. The ratio of emulsion height to total volume height was measured after 10 minutes and 1 hour, respectively. Commercially available surfactants rhamnolipid, cocoyl glucoside, and octyl / decyl glucoside were used as benchmarks. In addition to SBS1, three other surfactants, SBS2, SBS3, and SBS4, were also tested. As previously described, SBS1 is a glycolipid with a carbohydrate moiety of maltose and a lipid moiety of oleic acid (6- and / or 6'-oleoyl-maltose). 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).

[0120]

[0121] Emulsification data showed that, after both 10 minutes and 1 hour, the surfactants performed similarly for all tests except SBS2.

[0122] Therefore, SBS1, SBS3 and SBS4 can replace commonly used surfactants without sacrificing emulsifying ability.

[0123] Example 9 - Emulsifying ability of SBS1 with different chain lengths Emulsifying capacity was measured by mixing 1 mL of an aqueous solution of 1% surfactant with 1 mL of sunflower seed oil for 20 seconds to form an emulsion. These emulsions were then allowed to stand at room temperature for 17 hours, after which the emulsion phase was measured relative to the total volume.

[0124] As previously stated, SBS1 is a glycolipid with maltose as its carbohydrate moiety and oleic acid (6- and / or 6'-oleoyl-maltose) as its lipid moiety. SBS5 is a monoester glycolipid with maltose as its carbohydrate moiety and palmitic acid (6- and / or 6'-palmitoyl-maltose) as its lipid moiety. SBS6 is a monoester glycolipid with maltose as its carbohydrate moiety and myristic acid (6- and / or 6'-myristicoyl-maltose) as its lipid moiety. SBS7 is a monoester glycolipid with maltose as its carbohydrate moiety and lauric acid (6- and / or 6'-lauroyl-maltose) as its lipid moiety.

[0125]

[0126] The data shows that SBS1 exhibits very similar emulsifying capabilities across the C12-C18 chain length range.

[0127] Example 10 - Personal care product formulations of monoester glycolipids with different chain lengths The following personal hygiene product formulations were prepared. As previously described, SBS1 is a glycolipid with maltose as its carbohydrate moiety and oleic acid (6- and / or 6'-oleoyl-maltose) as its lipid moiety. SBS5 is a monoester glycolipid with maltose as its carbohydrate moiety and palmitic acid (6- and / or 6'-palmitoyl-maltose) as its lipid moiety. SBS6 is a monoester glycolipid with maltose as its carbohydrate moiety and myristic acid (6- and / or 6'-myristicoyl-maltose) as its lipid moiety. SBS7 is a monoester glycolipid with maltose as its carbohydrate moiety and lauric acid (6- and / or 6'-lauroyl-maltose) as its lipid moiety. SBS8 is a monoester glycolipid with maltose as its carbohydrate moiety and caprylic acid (6- and / or 6'-capryloyl-maltose) as its lipid moiety.

[0128]

[0129] Example 11 - Sulfate-free hand soap A sulfate-free hand soap was formulated using SBS1. The ingredients were mixed in the listed order with stirring, and the pH was finally adjusted to 5 with citric acid.

[0130] preparation

[0131] Example 12 - Hair Conditioner A conditioner containing SBS1 was formulated. The ingredients of Part 1 were mixed in the listed order until homogeneous. Similarly, the ingredients of Part 2 were mixed and then added to Part 1 while stirring. Finally, the pH was adjusted to obtain the final formulation.

[0132] preparation

[0133] Example 13 - Cleaning Wipes A solution containing SBS1 for cleaning wipes was tested. The ingredients were mixed in the listed order with stirring, and the pH was then adjusted to 5. The solution was then applied to the fabric for use as cleaning wipes.

[0134] preparation

[0135] Example 14 - Shampoo bar A shampoo bar containing SBS1 was formulated using the following ingredient list. The ingredients for Part 1 were dissolved together with water at 70°C and stirred until homogeneous. The ingredients for Part 2 were mixed, heated to 70°C, and stirred into Part 1. The mixture was cooled to below 45°C and the pH was adjusted to 5. The liquid was poured into the desired mold and cooled in the refrigerator until solid.

[0136] preparation

[0137] Example 15 - Cleansing Powder A flour-based preparation containing SBS1 was created. All ingredients were ground together to form a uniform powder. This powder works by dissolving in a small amount of hot water and foaming between the hands, producing a soap lather that can be applied to the face.

[0138] preparation

Claims

1. Use of monoester glycolipids or mixtures of monoester glycolipids in personal care products; wherein, The monoester glycolipid or mixture of monoester glycolipids includes the unmodified carbohydrate portion.

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

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

4. The use according to claim 1, wherein, The monoester glycolipid is 6-O-(lipid ester)-maltose and / or 6'-O-(lipid ester)-maltose.

5. The use according to claim 4, wherein, The 6-O-(lipid ester)-maltose and 6'-O-(lipid ester)-maltose are 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 claims 1-5, wherein, The monoester glycolipids include lipid fractions of diglycerides and / or triglycerides derived from sources selected from the following: sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, tallow, lard, rice bran oil, coconut oil, flaxseed oil, palm oil, shea butter, shea butter, and mixtures thereof.

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

8. The use according to any one of claims 1-6, wherein, The monoester glycolipid includes a lipid moiety having a chain length in the range of C8-C18, preferably in the range of C12-C18, and most preferably in the range of C16-C18.

9. A personal hygiene product composition comprising: - water; - Moisturizers and / or conditioning agents; and - Monoester glycolipids or mixtures of monoester glycolipids; wherein the monoester glycolipids or mixtures of monoester glycolipids include an unmodified carbohydrate portion.

10. The personal hygiene product composition according to claim 9, wherein, The monoester glycolipid or mixture of monoester glycolipids comprises an unmodified carbohydrate portion selected from the group consisting of maltose, cellobiose, and trehalose.

11. The personal hygiene product composition according to claim 9, wherein, The monoester glycolipid or mixture of monoester glycolipids includes an unmodified carbohydrate portion, which is maltose.

12. The personal hygiene product composition according to claim 9, wherein, The monoester glycolipid is 6-O-(lipid ester)-maltose and / or 6'-O-(lipid ester)-maltose.

13. The personal surface cleaning product composition according to claim 12, wherein, The 6-O-(lipid ester)-maltose and 6'-O-(lipid ester)-maltose are 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 hygiene product composition according to any one of claims 9-13, wherein, The monoglyceride glycolipids include lipid fractions derived from diglycerides and / or triglycerides selected from the following sources: sunflower oil, rapeseed oil, canola oil, olive oil, corn oil, soybean oil, peanut oil, tallow, lard, rice bran oil, coconut oil, flaxseed oil, palm oil, shea butter, shea butter, and mixtures thereof, preferably derived from sunflower oil.

15. The personal hygiene product composition according to any one of claims 9-14, wherein, The monoester glycolipid includes a lipid moiety having a chain length in the range of C6-C26, the lipid moiety being saturated or unsaturated with 1-6 double bonds, such as oleic acid and / or linoleic acid and / or stearic acid and / or palmitic acid and / or trans-palmitoyl oleate and / or palmitoleic acid.

16. The personal hygiene product composition according to any one of claims 9-14, wherein, The monoester glycolipid includes a lipid moiety having a chain length in the range of C8-C18, preferably in the range of C12-C18, and most preferably in the range of C16-C18.

17. The personal hygiene product composition according to any one of claims 9-16, wherein, The moisturizers and / or conditioning agents are 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 oat flour, vitamin E, cetyl alcohol, stearyl alcohol, behenyltrimethylammonium chloride, cetrimonium chloride, almond oil, avocado oil, olive oil, sunflower seed oil, glycolic acid, lactic acid, urea, sodium PCA, sorbitol, propylene glycol, caprylic / capric triglycerides, honey, beeswax, mango butter, rosehip oil, sweet almond oil, grapeseed oil, macadamia nut 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 soybean protein, hydrolyzed keratin, elastin, collagen, snail mucus, beta-glucan, oat kernel oil, rice bran oil, babassu seed oil, tamanu oil, black seed oil, chia seed oil, pumpkin seed oil, pomegranate oil, sea buckthorn oil, monoi oil, kukui nut oil, murumol palm oil, gupuasau fruit oil, Indian ironwood fruit oil, polyquaternium-7, polyquaternium-10, amino-terminated polydimethylsiloxane, cyclopentamethoxysiloxane and mixtures thereof.

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