Modified sophorolipids for hair and textile conditioning

Abstract

The present invention provides conditioning compositions for hair, fibers and textiles, the conditioning compositions comprising a derivatized cationic biosurfactant.

Description

[Technical field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims priority to U.S. Provisional Patent Application No. 63 / 314,757, filed February 28, 2022, which is incorporated by reference in its entirety. [Background technology]

[0002] background Consumers use and are exposed to household and personal care products every day. For example, most consumers' daily routines include the use of hair care, makeup, cleansers, laundry detergents, etc. Many of these types of products contain harsh chemicals as active ingredients, but may contain additives, such as fragrances, dyes, and additional chemicals that aid in properties such as viscosity, foaming, and solubility of the active ingredients.

[0003] One particular category of products of interest is hair care products. Hair shampoos clean hair by removing excess environmental dirt and sebum. Shampoos can also cause tangled and unmanageable hair, especially for long hair. Furthermore, when hair dries, it often removes the natural oils and other natural conditioning and moisturizing ingredients of hair, leaving hair dry, rough, static, lackluster, and / or frizzy.

[0004] To avoid these problems, hair conditioning compositions are typically applied to hair immediately after shampooing and rinsing. The conditioning composition is applied to hair and then may be used as a leave-on conditioner or may be rinsed off the hair with water. Similar types of compositions have also been used to condition textiles and fabrics.

[0005] Traditionally, hair and fabric conditioning compositions have utilized cationic surfactants. Cationic surfactants are those in which the surfactant activity resides in the positively charged cationic portion of the molecule. Thus, the cationic surfactant is attracted to the negatively charged hair or fabric surface and is deposited on the hair or fabric. Among cationic surfactants, quaternary ammonium compounds (QACs) are particularly suitable for treating hair or fabric. Thus, many conditioning products are based on quaternary ammonium compounds such as stearyl trimethyl ammonium chloride, behenyl trimethyl ammonium chloride, and distearyl dimethyl ammonium chloride.

[0006] Toxicity to humans and livestock is a short-term issue for existing personal care and household products. The environmental damage that can result from these ingredients is not yet fully understood, however, it is mainly dose-dependent. In some cases, QACs have been shown to persist in the environment. Although biodegradation pathways have been demonstrated under laboratory aerobic conditions, QACs, especially those containing aromatic scaffolds, tend to accumulate in environmental sludge and partition poorly into aqueous media. This removes QACs from aerobic environments where biodegradation can occur. The accumulation of QACs in anaerobic environmental sludge and soil poses a major challenge. Typical methods for removing other nitrogen-containing environmental contaminants, where both natural and human activities are promoted, are severely limited by the presence of QACs.

[0007] Although QAC biodegradation in anaerobic sludge environments is possible, the main degradation products of QACs include short alkylamines such as methylamines. Alkylamines can accumulate within microorganisms capable of degrading QACs, causing inhibition of QAC degrading enzymes and / or toxicity to the microorganisms themselves. Further complicating matters, QACs have been shown to inhibit methanogenesis and other anaerobic digestion pathways used by microorganisms to degrade other compounds. Thus, the risk of QACs in the environment is accompanied by the risk of accumulation of other hazardous chemicals that would normally be degraded.

[0008] In addition to the issue of QAC accumulation in the environment and its impact on microorganisms essential for biodegradation pathways, recent studies have suggested that environmental accumulation of QACs is accelerating the development of microorganisms resistant to conventional antibiotics. The same genes found to be responsible for conferring resistance to QACs in bacteria are associated with drug-resistant bacteria studied by medical researchers. This mechanism of resistance involves the use of efflux proteins with broad specificity for exogenous compounds. Thus, the use and environmental accumulation of QACs leads to the selection of bacteria that can be resistant to QACs and that are potentially resistant, unintentionally, to conventional antibiotics.

[0009] There are various naturally occurring substances that have been shown to have some degree of effectiveness as conditioning ingredients. One such substance is palm oil and its derivatives (palmitate, glyceryl, stearic acid, sodium laureth sulfate, sodium lauryl sulfate, etc.). In shampoos and conditioners, palm oil is used to restore the hair's natural oils that are stripped away by other cleansing chemicals present in most shampoos.

[0010] Although palm oil production and extraction is considered economically low cost, its environmental costs are of growing concern: mass palm oil production is destroying tropical rainforests, endangering native species, and polluting water sources due to mishandling of processing effluents.

[0011] Increasingly, consumers are seeking household and personal care products that are non-toxic, non-irritating to the skin and / or eyes, and have a low environmental impact, yet these safer and more sustainable products are expected to perform as well as conventional products in many attributes, such as hair and fiber conditioning. Formulating safe and environmentally friendly conditioning compositions remains a challenge, as there is a limited set of natural or sustainable materials that meet these needs.

[0012] Thus, there is a need for improved compositions that are effective in imparting the beneficial effects of conventional conditioners to hair and textiles, but which do not contain harmful or polluting chemicals or synthetically derived ingredients. Summary of the Invention

[0013] Quick Overview The present invention provides microbial-based products and their use in conditioning hair, fiber and textiles.More specifically, the present invention provides microbial-derived ingredients for use in formulating hair care products, household laundry products, and textile processing materials.Advantageously, in some embodiments, microbial-derived ingredients can be useful for replacing and / or reducing the use of traditional conditioning compounds such as QACs and palm oil.

[0014] In a preferred embodiment, the present invention provides microbially derived surfactants, or biosurfactants, for use in conditioning formulations for hair, laundry, and textile fibers. In certain embodiments, the biosurfactants are derivatized and / or purified to create and / or enhance one or more desired functions, preferably conditioning functions.

[0015] In some embodiments, conditioning functions include one or more of the following non-limiting examples: reducing static and / or frizz; increasing strength; reducing breakage; reducing tangling and matting; improving shine and softness; increasing oil and / or water retention; reducing wrinkles; and / or imparting fragrance.

[0016] In certain embodiments, the biosurfactant is a glycolipid, for example, selected from sophorolipids (SLPs), mannosylerythritol lipids (MELs), rhamnolipids (RLPs), and trehalose lipids (TLs).

[0017] In certain embodiments, the biosurfactant comprises a sophorolipid or a mixture of SLP molecules, including, for example, lactone-type SLPs, linear SLPs, deacetylated SLPs, monoacetylated SLPs, diacetylated SLPs, esterified SLPs, SLPs with various hydrophobic chain lengths, SLPs with fatty acid-amino acid complexes attached, and others, including those specifically exemplified and / or not exemplified in this disclosure.

[0018] In certain preferred embodiments, the biosurfactant is a derivatized SLP or a mixture of derivatized SLPs, where the molecular structure of the SLP molecules is modified to produce linear (acidic) cationic SLP derivatives. More specifically, in preferred embodiments, the linear cationic SLP derivatives are modified to include cationic amino acid residues such as arginine, lysine or histidine; peptides containing arginine, lysine and / or histidine repeats; or peptides containing glycine spacers between individual amino acids and / or between the SLP scaffold and the amino acid or peptide residue.

[0019] In certain embodiments, the derivatized cationic SLPs according to the present invention can be used as active ingredients in environmentally friendly conditioning compositions for hair, fibers and textiles. Advantageously, in preferred embodiments, the compositions and methods are conditioners that are at least as effective as QACs, and other synthetic cationic conditioning ingredients, as well as palm oil.

[0020] In certain embodiments, the conditioning composition may further comprise additional biosurfactants.For example, in some embodiments, the conditioning composition comprises a derivatized linear cationic SLP and one or more other SLP molecules that are not derivatized according to the present invention.In other embodiments, the conditioning composition comprises a derivatized linear cationic SLP and one or more MEL molecules.In yet another exemplary embodiment, the conditioning composition comprises a derivatized linear cationic SLP, one or more other SLP molecules, and one or more MEL molecules.

[0021] Optionally, the conditioning composition may further comprise one or more other ingredients including, for example, a carrier (e.g., water), a solvent, an organic and / or inorganic acid, an essential oil, a botanical extract, a crosslinking agent, a chelating agent, a fatty acid, an alcohol, a pH adjuster, a reducing agent, a buffer, an enzyme, a dye, a colorant, a fragrance, a preservative, an emulsifier, a foaming agent, a bleaching agent, a polymer, a thickener, and / or a viscosity modifier.

[0022] In some embodiments, the conditioning composition can be used in hair care products, such as shampoos, conditioners or cream rinses, detanglers, or styling products. In some embodiments, the conditioning composition can be used in household or industrial laundry products, such as fabric softeners or dryer sheets. In some embodiments, the conditioning composition can be used in the treatment of raw fibers or fabrics for conditioning prior to the assembly of garments, rugs, and other textiles.

[0023] In a preferred embodiment, the present invention further provides a method for conditioning hair, fibers or textiles, wherein the method comprises contacting the hair, fibers or textiles with the conditioning composition of the present invention for a sufficient amount of time to impart a conditioning effect thereto. In some embodiments, the composition is applied in the presence of water or another solvent. In some embodiments, the composition is washed off the hair, fibers or textiles after contacting them, while in other embodiments, the composition is left in place without being washed off.

[0024] Advantageously, the method is safe for use, for example, in household, commercial, medical and industrial settings, and in the presence of humans, plants and animals.In addition, the conditioning composition of the present invention can be manufactured and used without harming users and without releasing large amounts of polluting and toxic compounds into the environment.In addition, the composition and method utilize biodegradable and toxicologically safe ingredients.Therefore, the present invention can be used in various industries as a "green" conditioning ingredient. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0025] Detailed Description The present invention provides microbial-based products and their use in conditioning hair, fiber and textiles.More specifically, the present invention provides microbial-derived ingredients for use in formulating hair care products, household laundry products, and textile processing materials.Advantageously, in some embodiments, microbial-derived ingredients can be useful for replacing and / or reducing the use of traditional conditioning compounds such as QACs and palm oil.

[0026] In a preferred embodiment, the present invention provides microbially derived surfactants, or biosurfactants, for use in conditioning formulations for hair, laundry, and textile fibers. Biosurfactants are amphiphilic molecules consisting of both hydrophobic domains (e.g., fatty acids) and hydrophilic domains (e.g., sugars). Due to their amphiphilic nature, biosurfactants can partition at interfaces between different fluid phases, such as the oil / water or water / air interface. Unlike synthetic surfactants, biosurfactants can be effective in both hot and cold water and at either extreme of the pH scale. Furthermore, biosurfactants are biodegradable and non-toxic.

[0027] Glycolipid biosurfactants have many important physiological roles in cell biology, especially as major components of cell membranes, but they have recently attracted attention because they may serve as biological alternatives to outdated surfactants.

[0028] In certain embodiments of the present invention, sophorolipids (SLPs) are particular glycolipids of interest. Sophorolipids are glycolipid biosurfactants produced, for example, by various yeasts of the Starmerella clade. SLPs consist of the disaccharide sophorose linked to a long-chain hydroxy fatty acid. They can contain partially acetylated 2-O-β-D-glucopyranosyl-D-glucopyranose units β-glycosidically linked to 17-L-hydroxyoctadecanoic acid or 17-L-hydroxy-Δ9-octadecenoic acid. The hydroxy fatty acid can have, for example, 11 to 20 carbon atoms and may contain one or more unsaturated bonds. Furthermore, the sophorose residues can be acetylated at the 6 and / or 6' positions. The fatty acid carboxyl group may be free (acid or linear) or internally esterified at the 4" position (lactone). In most cases, fermentation of SLPs results in a mixture of hydrophobic (water-insoluble) SLPs, including, for example, lactone SLPs, monoacetylated linear SLPs, and diacetylated linear SLPs, and hydrophilic (water-soluble) SLPs, including, for example, nonacetylated linear SLPs.

[0029] As used herein, the terms "sophorolipid," "sophorolipid molecule," "SLP," or "SLP molecule" include all forms of SLP molecules and their isomers, including, for example, acidic (linear) SLPs and lactone-type SLPs. Additionally, monoacetylated SLPs, diacetylated SLPs, esterified SLPs, SLPs with various hydrophobic chain lengths, SLPs with fatty acid-amino acid complexes attached, and others, including those described and / or not described in this disclosure.

[0030] In some embodiments, the SLP molecules can be represented by general formula (1) and / or general formula (2), and include different fatty acid chain lengths (R 3 ), and in some cases, R 1 and / or R 2 It is obtained as a collection of more than 30 structural homologues, each of which is acetylated or protonated at 100°C. TIFF2025506856000001.tif45145

[0031] In the general formula (1) or (2), R 0 R can be either a hydrogen atom or a methyl group. 1 and R 2 R is independently a hydrogen atom or an acetyl group. 3 is a saturated aliphatic hydrocarbon chain or an unsaturated aliphatic hydrocarbon chain having at least one double bond, and may bear one or more substituents.

[0032] Non-limiting examples of substituents include halogen atoms, hydroxyl, lower (C1-6) alkyl groups, halo lower (C1-6) alkyl groups, hydroxy lower (C1-6) alkyl groups, halo lower (C1-6) alkoxy groups, and others such as those described in this disclosure. 3 can have, for example, 11 to 20 carbon atoms.

[0033] Fermentation of yeast cells in a culture substrate containing sugars and / or lipids and fatty acids with different carbon chain lengths can be used to produce a variety of SLPs. The yeast Starmerella (Candida) bombicola is one of the most widely recognized producers of SLPs. Typically, this yeast produces both lactone-type SLPs and linear SLPs during fermentation, with approximately 60-70% of the SLPs being composed of lactone forms and the remainder being composed of linear forms.

[0034] Selected Definitions As used herein, the term "conditioning," as applicable to hair, fibers and / or textiles, refers to one or more of the following non-limiting examples: reducing static and / or frizz; increasing strength; reducing breakage; reducing tangles and matting; improving shine and softness; increasing oil and / or moisture retention; reducing wrinkles; and / or imparting fragrance.

[0035] As used herein, "dermatologically acceptable," "cosmetically acceptable," and "topically acceptable" are used interchangeably and are intended to mean that a particular ingredient is safe and non-toxic for application to the integument (e.g., skin, scalp) at the levels used. In one embodiment, the ingredients of the composition are recognized as Generally Regarded as Safe (GRAS).

[0036] As used herein, the term "effective amount" refers to an amount of something (e.g., compound, composition, time) that can achieve a desired amount of conditioning in hair, fibers and / or textiles. The actual amount will vary depending on a number of factors, including, but not limited to, the amount of conditioning required, the type of hair, fibers and / or textiles, and the method of administration.

[0037] As used herein, a "microbe-based composition" refers to a composition that includes components produced as a result of the growth of a microorganism or other cell culture. Thus, a microorganism-based composition may include the microorganism itself and / or by-products of microbial growth (e.g., biosurfactants, solvents and / or enzymes). The cells may be in vegetative or spore form, or a mixture of both. The cells may be in planktonic or biofilm form, or a mixture of both. The cells may be live or inert, intact or lysed. The cells may be removed from the medium in which they were grown, or may be present in a concentration of, for example, at least 1 x 10 per milliliter of composition. 3 , 1 x 10 4 , 1 x 10 5 , 1 x 10 6 , 1 x 10 7 , 1 x 10 8 , 1 x 10 9 , 1 x 10 10 , or 1 x 10 11The cells may be present at a concentration of 1000 μg / ml or more. In one embodiment, the microorganism-based composition comprises only the medium in which the cells have been grown and the cells have been removed (although in some cases some residual cellular material may remain in the medium). By-products of growth may be present in the medium and may include, for example, metabolic products, cell membrane components, expressed proteins, and / or other cellular components. In one embodiment, the microorganism-based composition comprises only microbial growth by-products.

[0038] The present invention further provides a "microbe-based product", which is a product that is actually applied to achieve a desired result. The microbe-based product may simply be a microbe-based composition harvested from a microbe culturing process. Alternatively, the microbe-based product may include additional components added. These additional components may include, for example, stabilizers, buffers, carriers, and other additives and / or adjuvants suitable for a particular application. The microbe-based product may also include a mixture of the microbe-based composition. The microbe-based product may also include one or more components of the microbe-based composition that have been processed in some way, such as, but not limited to, filtering, centrifuging, dissolving, drying, purifying, etc.

[0039] "Metabolite" refers to a substance produced by metabolism (e.g., a growth by-product) or a substance required to participate in a particular metabolic process. Examples of metabolites include, but are not limited to, enzymes, acids, solvents, alcohol, proteins, carbohydrates, vitamins, minerals, trace elements, amino acids, polymers, and biosurfactants.

[0040] As used herein, the terms "isolated" or "purified" when used in reference to a biological or natural substance, such as a nucleic acid molecule, polynucleotide, polypeptide, protein, organic compound, e.g., a small molecule, microbial cell / strain, or host cell, means that the substance is substantially free of other compounds, such as cellular material, with which it is associated in nature, i.e., the substance does not occur in nature without these other compounds and / or has different or unique properties compared to those found in the naturally occurring material.

[0041] In some embodiments, the purified compound is at least 60% by weight of the compound of interest.Preferably, the preparation is at least 75% by weight, more preferably at least 90% by weight, and most preferably at least 99% by weight or 100% by weight (w / w) of the desired compound.Purity is measured by any suitable standard method, for example, by column chromatography, thin layer chromatography, or high performance liquid chromatography (HPLC) analysis.

[0042] As used herein, "isomer" refers to a molecule that has the same chemical formula as another molecule, but has a unique structure. Isomers can be structural isomers, in which atoms and functional groups are bonded at different locations, and stereoisomers (spatial isomers), in which the bond structure is the same, but the geometric positions of atoms and functional groups in space are different. For example, MEL isomers can differ in the bond types and positions of carbohydrates, fatty acids, and / or acetyl groups.

[0043] As used herein, the term "subject" refers to an animal, preferably a mammal.In the context of the present invention, the preferred subject is human.Subject can be of any gender and of any age or development stage, including infants, toddlers, adolescents, teenagers, young adults, middle-aged people, or elderly people.

[0044] As used herein, "surfactant" refers to a surface-active substance or compound that reduces the surface tension (or interfacial tension) between two phases. Surfactants act, for example, as detergents, wetting agents, emulsifiers, foaming agents, and / or dispersants. "Biosurfactant" refers to a surfactant produced by living organisms and / or produced using naturally occurring substrates.

[0045] Generally, "textile" refers to a flexible material, such as a fabric, cloth, or carpet, made by interlocking yarns or threads produced by spinning raw fibers into long twisted lengths. Interlocking can be accomplished, for example, by weaving, knitting, crocheting, knotting, tatting, felting, gluing, or braiding. In addition to flexible materials, "textile" as used herein can also include finished products made using the flexible materials, as well as the raw materials involved in the manufacture of the flexible materials, including raw fibers, yarns, and threads. In some embodiments, finished textiles include clothing, upholstery, draperies, carpets, and rugs. In some embodiments, textiles can also include paper products.

[0046] Textiles can be made, for example, from protein-rich sources (e.g., wool, silk, hair, fur), cellulose-rich sources (e.g., cotton, flax, hemp, coconut, wood, and other plants), mineral (e.g., asbestos), synthetic sources (e.g., polyamines, polyesters, acrylonitrile, polyurethanes, and other polymers).

[0047] As used herein, "topical" means suitable for external local application to the skin, scalp, or hair. In other words, topical compositions are not intended to be applied to a subject via oral, intravenous, intramuscular, intrathecal, subcutaneous, sublingual, buccal, rectal, intravaginal, inhalation, ocular, or otic routes.

[0048] The transitional term "comprising," which is synonymous with "including" or "containing," is inclusive or open-ended and does not exclude additional, unrecited elements or method steps. In contrast, the transitional phrase "consisting of" excludes elements, steps, or ingredients not specified in the claim. The transitional phrase "consisting essentially of" limits the scope of the claim to the specified materials or steps, "and which do not materially affect the basic and novel characteristic(s) of the claimed invention." Use of the term "comprising" contemplates other embodiments that "consist" or "consist essentially of" the recited ingredient(s).

[0049] As used herein, the term "or" is understood to be inclusive unless otherwise stated or clear from context. As used herein, the terms "a," "an," and "the" are understood to be singular or plural unless otherwise stated or clear from context.

[0050] Unless otherwise specified or clear from the context, as used herein, the term "about" is understood to mean within normal tolerances in the art, for example, within 2 standard deviations of the mean. "About" may be understood to mean within 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1%, 0.5%, 0.1%, 0.05%, or 0.01% of the stated value.

[0051] The recitation of a list of chemical groups in any definition of a variable herein includes a definition of that variable as any single group or combination of listed groups. The recitation of an embodiment of a variable or aspect herein includes that embodiment as any single embodiment or in combination with any other embodiment or portion thereof.

[0052] Any composition or method provided herein can be combined with one or more of any of the other compositions and methods provided herein.Other features and advantages of the present invention will be apparent from the following description of its preferred embodiments and from the claims.All references cited herein are incorporated herein by reference.

[0053] Conditioning Composition The present invention provides microbial-based products and their use in conditioning hair, fiber and textiles.More specifically, the present invention provides microbial-derived ingredients for use in formulating hair care products, household laundry products, and textile processing materials.Advantageously, in some embodiments, microbial-derived ingredients can be useful for replacing and / or reducing the use of traditional conditioning compounds such as QACs and palm oil.

[0054] In some embodiments, the conditioning composition can be used in hair care products, such as shampoos, conditioners or cream rinses, detanglers, or styling products. In some embodiments, the conditioning composition can be used in household or industrial laundry products, such as fabric softeners or dryer sheets. In some embodiments, the conditioning composition can be used in the treatment of raw fibers or fabrics for conditioning prior to the assembly of garments, fabrics, rugs, and other textiles.

[0055] In a preferred embodiment, the present invention provides microbially derived surfactants, or biosurfactants, for use in conditioning formulations for hair, laundry, and textile fibers. In certain embodiments, the biosurfactants are derivatized and / or purified to create and / or enhance one or more desired functions, preferably conditioning functions.

[0056] In certain embodiments, the biosurfactant is a glycolipid, for example, selected from sophorolipids (SLPs), mannosylerythritol lipids (MELs), rhamnolipids (RLPs), and trehalose lipids (TLs).

[0057] In some embodiments, biosurfactant is utilized in crude form, where biosurfactant molecules are present in the growth medium (e.g., broth) in which biosurfactant-producing microorganisms are cultured and collected from there without purification. Crude form may, for example, contain at least 0.001%, 1%, 5%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90% or 99% amphiphilic molecules in the growth medium. In alternative embodiments, biosurfactant is extracted from the growth medium and optionally derivatized and / or purified.

[0058] In certain embodiments, the biosurfactant comprises a sophorolipid or a mixture of SLP molecules, including, for example, lactone-type SLPs, linear SLPs, deacetylated SLPs, monoacetylated SLPs, diacetylated SLPs, esterified SLPs, SLPs with various hydrophobic chain lengths, SLPs with fatty acid-amino acid complexes attached, and others, including those specifically exemplified and / or not exemplified in this disclosure.

[0059] In certain preferred embodiments, the biosurfactant is a derivatized SLP or a mixture of derivatized SLPs, where the molecular structure of the SLP molecules is modified to produce linear (acidic) cationic SLP derivatives. More specifically, in preferred embodiments, the linear cationic SLP derivatives are modified to include cationic amino acid residues such as arginine, lysine or histidine; peptides containing arginine, lysine and / or histidine repeats; or peptides containing glycine spacers between individual amino acids and / or between the SLP scaffold and the amino acid or peptide residue.

[0060] In some embodiments, the derivatized SLPs have a formula according to general formula (3), (4), (5), or (6), where R = lysine, histidine, glyine, arginine, or a peptide containing repeats of lysine, histidine, and / or arginine, and R1 = H, acetyl, butyl, or isobutyl. TIFF2025506856000002.tif174147TIFF2025506856000003.tif49157

[0061] In certain embodiments, the conditioning composition comprises derivatized SLPs of general formulas (3)-(6) at a dosage rate of from about 100 ppm to about 250,000 ppm, from about 200 ppm to about 100,000 ppm, from about 300 ppm to about 75,000 ppm, from about 400 ppm to about 50,000 ppm, or from about 500 ppm to about 25,000 ppm.

[0062] In certain embodiments, the conditioning composition comprises a derivatized SLP at a dosage rate of about 0.01 wt % to about 25 wt %, about 0.05 wt % to about 20 wt %, about 0.1 wt % to about 15 wt %, or about 0.5 wt % to about 10 wt %.

[0063] In certain embodiments, the conditioning composition may further comprise an additional biosurfactant. For example, in some embodiments, the conditioning composition comprises a derivatized linear cationic SLP and one or more other SLP molecules that are not derivatized according to the present invention.

[0064] The mixing ratio of cationic derivatized SLPs to underivatized SLPs can range from 1:1 to 1:1000, 1:5 to 1:500, or 1:10 to 1:100.

[0065] In other embodiments, the conditioning composition comprises a derivatized linear cationic SLP and one or more mannosylerythritol lipid (MEL) molecules.

[0066] The mixing ratio of cationic derivatized SLPs to MEL can range from 1:1 to 1:1000, 1:5 to 1:500, 1:10 to 1:100, 1000:1 to 1:1, 500:1 to 5:1, or 100:1 to 10:1.

[0067] In yet another exemplary embodiment, the conditioning composition comprises a derivatized linear cationic SLP, one or more other SLP molecules, and one or more MEL molecules.

[0068] In one embodiment, MEL comprises either 4-OBD-mannopyranosyl-meso-erythritol or 1-OBD-mannopyranosyl-meso-erythritol as the hydrophilic portion, and a fatty acid group and / or an acetyl group as the hydrophobic portion. One or two of the hydroxyls may be acetylated, typically at C4 and / or C6 of the mannose residue. Additionally, there may be one to three esterified fatty acids with chain lengths of 8-12 carbons or more.

[0069] MEL and MEL-like substances (e.g., mannose-based substances) are produced primarily by Pseudozyma species (e.g., P. aphidis) and Ustilago species (e.g., U. maydis), with significant differences between the MEL structures produced by each species. Some mannose-based substances with properties similar to MEL can also be produced by the yeast Meyerozyma guilliermondii.

[0070] MEL is non-toxic and stable over wide temperature and pH ranges. Moreover, MEL may be used without added preservatives.

[0071] MEL can be produced in over 93 different combinations that fall into five major categories: MEL A, MEL B, MEL D, triacetylated MEL A, and triacetylated MEL B / C. These molecules can be modified synthetically or naturally. For example, MEL can contain different carbon chain lengths or different numbers of acetyl and / or fatty acid groups.

[0072] MEL molecules and / or modified forms thereof in accordance with the present invention can include, for example, triacylated, diacylated, monoacylated, triacetylated, diacetylated, monoacetylated and non-acetylated MEL, as well as stereoisomers and / or structural isomers thereof.

[0073] Other mannose-based / MEL-like substances exhibiting similar structures and similar properties, such as mannosyl-mannitol lipids (MML), mannosyl-arabitol lipids (MAL), and / or mannosyl-ribitol lipids (MRL), can also be used in accordance with the present invention.

[0074] In some embodiments, the composition comprises a carrier.Non-limiting examples of carriers include, for example, water; saline; saline; ointment; cream; oil-in-water emulsion; water-in-oil emulsion; silicone-in-water emulsion; water-in-silicone emulsion; wax-in-water emulsion; water-oil-water triple emulsion; microemulsion; gel; vegetable oil; mineral oil; ester oil, for example, octal palmitate, isopropyl myristate and isopropyl palmitate; ether, for example, dicapryl ether and dimethyl isosorbide; alcohol, for example, ethanol and isopropanol; fatty alcohol, for example, cetyl alcohol, cetearyl alcohol, stearyl alcohol and behenyl alcohol; isoparaffin, for example, isooctane, isododecane (IDD) and isohexadecane; silicone oil, for example, cyclomethicone, dimethicone, dimethicone crosspolymer, polysiloxane and derivatives thereof, preferably. or organic modified derivatives including PDMS, dimethicone copolyol, dimethiconol, and amodimethiconol; hydrocarbon oils such as mineral oil, petrolatum, isoeicosane, and polyolefins such as (hydrogenated) polyisobutene; polyols such as propylene glycol, glycerin, butylene glycol, pentylene glycol, hexylene glycol, caprylyl glycol; waxes such as beeswax, carnauba, ozokerite, microcrystalline wax, polyethylene wax, and vegetable wax; or any combination or mixture of the foregoing. The aqueous vehicle may include one or more solvents miscible with water, including lower alcohols such as ethanol, isopropanol, and the like. The vehicle may comprise about 1% to about 99% by weight, 10% to about 85%, 25% to 75%, or 50% to about 65% of the composition.

[0075] Optionally, the conditioning composition may contain, for example, organic and / or inorganic solvents, organic and / or inorganic acids, essential oils, botanical extracts, crosslinkers, chelating agents, fatty acids, alcohols, pH adjusters, reducing agents, buffers, enzymes, dyes, colorants, fragrances, preservatives, emulsifiers, demulsifiers, foaming agents, defoamers, bleaching agents, emollients, humectants, anti-inflammatory agents, polymers, stabilizers, silicones, thickeners, softeners, UV blocking agents, moisturizers, film formers, minerals, vitamins, proteins, viscosity and / or rheology modifiers, insect repellents, skin cooling compounds, skin protection agents, and the like. The composition may further comprise one or more other ingredients relevant to a particular application, including protective agents, lubricants, pearls, chromalite, mica, antiallergic agents, antimicrobial agents (e.g., antifungal, antiviral, antibacterial agents), preservatives, pharmaceuticals, light stabilizers, surface smoothers, optical diffusers, exfoliation enhancers, antistatic agents, anti-wrinkle agents, humectants, dye transfer aids, color protection agents, odor control agents, odor traps, detergents, drying agents, water repellents, anti-pilling agents, acidulants, sizing agents, optical brighteners, antioxidants, shrinkage control agents, starches, and mixtures thereof.

[0076] The amount of each ingredient, whether active or inactive, is that conventionally used in cosmetics / personal care, textile processing and laundry care to achieve its intended purpose, typically ranging from about 0.0001% to about 25%, or from about 0.001% to about 20% of the composition, although the amount may be outside these ranges. The nature of these ingredients and their amounts must be compatible with the manufacture and function of the composition of the present disclosure. In a preferred embodiment, the composition includes additives that are considered dermatologically acceptable.

[0077] In certain embodiments, the composition may include a pH adjuster (e.g., citric acid, ethanolamine, sodium hydroxide, etc.) formulated within a wide range of pH levels. In one embodiment, the pH of the conditioning composition ranges from 1.0 to 13.0. In some embodiments, the pH of the conditioning composition ranges from 2.0 to 12.0. In some embodiments, the pH of the composition is 3.0 to 7.0 or 3.0 to 8.0.

[0078] The present invention can take any number of forms, including, for example, liquids, colloidal dispersions, micro- or nano-emulsions, gels, serums, granular, spray-dried or dry blend powders, solid bars, concentrates, encapsulated soluble pods, suspensions, hydrogels, multi-phase solutions, vesicular dispersions, foams, mousses, sprays, aerosols, liquid cakes, ointments, essences, pastes, tablets, water-soluble sheets or sachets, and / or can be impregnated into dry or wet substrates such as sheets (e.g., dryer sheets), balls (e.g., wool dryer balls), cloths, sponges or wipes.

[0079] Methods for conditioning hair, fibers and textiles In a preferred embodiment, the present invention further provides a method for conditioning hair, fibers or textiles, the method comprising contacting the hair, fibers or textiles with the conditioning composition of the present invention for an effective amount of time to impart a conditioning effect thereto. In some embodiments, the composition is applied in the presence of water or another solvent. In some embodiments, the composition is rinsed from the hair, fibers or textiles after contacting them.

[0080] In the context of hair conditioner, the method may include contacting hair with the composition.In some embodiments, the composition is contacted with hair while the hair is wet, while in other embodiments, the hair is dry.Applying may include lathering or rubbing the composition into hair; spraying the composition into hair; combing the composition into hair; and / or other standard application methods for hair care products.

[0081] In some embodiments, the composition is applied to the hair simultaneously with shampooing or after shampooing the hair (i.e., after the hair has been washed and rinsed). The conditioning composition can be left on the hair as a leave-in conditioning treatment, or the composition can be rinsed after contact for, for example, at least 15 seconds, at least 30 seconds, at least 1 minute, at least 5 minutes, up to at least 60 minutes.

[0082] In the context of fabric conditioners, the composition can be contacted with fibers utilized in the construction of garments and other textiles, hi some embodiments, the fibers are contacted with the composition prior to being constructed into a textile.

[0083] Chemical surfactants are often used to scour or wash raw fibers before further processing. Because scouring can dry out the fibers, conditioning or lubrication is necessary before the fibers are spun, coated, or woven into textiles. Thus, in some embodiments, a conditioning composition can be contacted with the fibers to lubricate and soften the fibers, thereby reducing breakage, dryness, static electricity, and / or stiffness after scouring.

[0084] In the context of textile conditioning, the method can be utilized in the finishing stage of textile manufacturing, and in domestic and industrial laundries.For example, in some embodiments, the conditioning composition is utilized in the form of a fabric softener that is applied to clothing and other textiles during standard wash cycle, during drying cycle, or as a spray on wet or dry textiles.

[0085] Preparation of derivatized cationic SLP molecules The present invention provides materials and methods for producing, derivatizing, and purifying sophorolipids (SLPs). Advantageously, the present invention uses safe and environmentally friendly materials and processes suitable for industrial-scale production of purified SLP derivatives.

[0086] In preferred embodiments, the method includes first producing a standardized SLP molecular "substrate" for producing derivatized and / or purified SLPs, which in some embodiments includes culturing sophorolipid-producing yeast in a submerged fermentation reactor with a regulated oleochemical feedstock to produce a yeast culture product, said yeast culture product including fermentation broth, yeast cells, and SLPs having a mixture of two or more molecular structures.

[0087] The mixture of molecular structures can include, for example, lactone-type SLPs, linear SLPs, deacetylated SLPs, monoacetylated SLPs, diacetylated SLPs, esterified SLPs, SLPs with various hydrophobic chain lengths, SLPs with fatty acid-amino acid complexes attached, and others including those described and / or not described in this disclosure.

[0088] In certain embodiments, the distribution of the mixture of SLP molecules can be altered by adjusting fermentation parameters such as, for example, feedstock, fermentation time, and dissolved oxygen levels.

[0089] As used herein, "fermentation" refers to the growth or cultivation of cells under controlled conditions. Growth can be aerobic or anaerobic. Unless the context indicates otherwise, the phrase is intended to encompass both the growth and product biosynthesis phases of the process.

[0090] As used herein, "broth," "culture broth," or "fermentation broth" refers to a culture medium that contains at least nutrients. When the broth is referred to after a fermentation process, the broth may also contain microbial growth by-products and / or microbial cells.

[0091] The microbial growth vessel used according to the present invention can be any fermenter or culture reactor for industrial use. As used herein, the terms "reactor", "bioreactor", "fermentation reactor" or "fermentation vessel" include fermentation equipment consisting of one or more vessels and / or towers or piping arrangements. Examples of such reactors include, but are not limited to, continuous stirred tank reactors (CSTRs), immobilized cell reactors (ICRs), trickle bed reactors (TBRs), bubble columns, gas lift fermenters, static mixers, or other vessels or other devices suitable for gas-liquid contact. In some embodiments, a bioreactor may include a first growth reactor and a second fermentation reactor. Thus, when referring to the addition of substrate to a bioreactor or fermentation reaction, it should be understood to include addition to either or both of these reactors, as appropriate.

[0092] In one embodiment, the fermentation reactor may have or be connected to functional controls / sensors to measure important factors in the cultivation process, such as pH, oxygen, pressure, temperature, agitator shaft power, humidity, viscosity and / or microbial density and / or metabolite concentration.

[0093] In further embodiments, the container may also be capable of monitoring the growth of microorganisms within the container (e.g., measuring cell count and growth phase). Alternatively, samples may be taken from the container for enumeration, purity measurement, SLP concentration, and / or visual oil level monitoring. For example, in one embodiment, sampling may be performed every 24 hours.

[0094] Microbial inocula according to the present methods preferably contain cells and / or growths of the desired microorganism and can be prepared using any known fermentation method. The inocula can be premixed with water and / or liquid growth medium, if desired.

[0095] The microorganisms utilized according to the present invention may be natural microorganisms or genetically modified microorganisms. For example, microorganisms may be transformed with specific genes to exhibit specific characteristics. Microorganisms may also be mutants of desired strains. As used herein, "mutant" refers to a strain, genetic variant or subtype of a reference microorganism, where the mutant has one or more genetic mutations (e.g., point mutations, missense mutations, nonsense mutations, deletions, duplications, frameshift mutations or repeat expansions) compared to the reference microorganism. Procedures for making mutants are well known in the art of microbiology. For example, UV mutagenesis and nitrosoguanidine are widely used for this purpose.

[0096] In a preferred embodiment, the microorganism is a yeast or fungus. Examples of yeast and fungal species suitable for use according to the present invention include, but are not limited to, Starmerella spp. yeast and / or Candida spp. yeast, such as Starmerella (Candida) bombicola, Candida apicola, Candida batistae, Candida floricola, Candida riodocensis, Candida stellate and / or Candida kuoi. In a particular embodiment, the microorganism is Starmerella bombicola, such as the ATCC 22214 strain.

[0097] In some embodiments, the culture method utilizes submerged fermentation in a liquid growth medium that includes a conditioned oleochemical feedstock.

[0098] In one embodiment, the liquid growth medium comprises one or more carbon sources. The carbon source can be carbohydrates, such as glucose, dextrose, sucrose, lactose, fructose, trehalose, mannose, mannitol, and / or maltose; organic acids, such as acetic acid, fumaric acid, citric acid, propionic acid, malic acid, malonic acid, and / or pyruvic acid; alcohols, such as ethanol, propanol, butanol, pentanol, hexanol, isobutanol, and / or glycerol; fats and oils, such as canola oil, madofuka oil, soybean oil, rice bran oil, olive oil, corn oil, sunflower oil, sesame oil, and / or linseed oil; powdered molasses, etc. These carbon sources can be used independently or in combination of two or more.

[0099] In a preferred embodiment, the fermentation medium comprises dextrose. In another preferred embodiment, the oleochemical feedstock is adjusted to include a source of oleic acid. In certain embodiments, the oleic acid content is high, e.g., at least 75%, at least 80%, at least 85%, at least 90%, at least 95%, or at least 99%. In some embodiments, the oleochemical feedstock comprises exclusively an oleic acid source.

[0100] Examples of oleic acid sources include, but are not limited to, high oleic soybean oil, high oleic sunflower oil, high oleic canola oil, olive oil, pecan oil, peanut oil, macadamia oil, grapeseed oil, sesame oil, poppy seed oil, pure oleic acid, Madofuka oil, oleic acid alkyl esters, and / or triglycerides of oleic acid. In a preferred embodiment, high oleic soybean oil, pure oleic acid, and / or oleic acid alkyl esters are used.

[0101] Advantageously, in some embodiments, the use of high oleic acid and / or exclusive oleic acid oleochemical feedstocks results in yeast culture products that contain a narrower diversity of SLP molecular structures than do feedstocks containing other sources of fatty acids, where the majority of SLP molecules produced contain a C18 carbon chain and a single unsaturated bond at carbon 9. For example, in some embodiments, greater than 50%, preferably greater than 70%, and more preferably greater than 85% of the SLP molecules contain a C18 carbon chain.

[0102] In one embodiment, the liquid growth medium comprises a nitrogen source. The nitrogen source can be, for example, yeast extract, potassium nitrate, ammonium nitrate, ammonium sulfate, ammonium phosphate, ammonia, urea, and / or ammonium chloride. These nitrogen sources can be used independently or in combination of two or more.

[0103] In one embodiment, one or more inorganic salts may also be included in the liquid growth medium. Inorganic salts may include, for example, potassium dihydrogen phosphate, monopotassium phosphate, dipotassium hydrogen phosphate, disodium hydrogen phosphate, potassium chloride, magnesium sulfate, magnesium chloride, ferrous sulfate, ferrous chloride, manganese sulfate, manganese chloride, zinc sulfate, lead chloride, copper sulfate, calcium chloride, calcium carbonate, calcium nitrate, magnesium sulfate, sodium phosphate, sodium chloride, and / or sodium carbonate. These inorganic salts may be used independently or in combination of two or more.

[0104] In one embodiment, the medium contains growth factors and micronutrients for the microorganism.Inorganic nutrients, including trace elements such as iron, zinc, copper, manganese, molybdenum, cobalt, etc., may also be included in the medium.In addition, sources of vitamins, essential amino acids, proteins and trace elements, such as corn flour, peptone, yeast extract, potato extract, beef extract, soybean extract, banana peel extract, etc., may be included or in purified form.Amino acids, such as those useful for protein biosynthesis, may also be included.

[0105] The culture method can provide further oxygenation to the growing culture. One embodiment utilizes slow motion of air to remove low oxygen containing air and introduce oxygenated air. The oxygenated air can be ambient air that is replenished daily through a mechanism that includes an impeller for mechanical agitation of the liquid and an air sparger to provide air bubbles to the liquid for dissolution of oxygen into the liquid.

[0106] In some embodiments, dissolved oxygen (DO) levels are controlled during fermentation to narrow the structural diversity of SLP molecules produced in the yeast culture product. Preferably, DO levels are maintained at high levels, e.g., such that oxygen transfer occurs at rates of 50 mM or more, 55 mM or more, 60 mM or more, 65 mM or more, or 70 mM or more per liter per hour.

[0107] In some embodiments, the culture method may further include adding additional acid and / or antibacterial agents to the liquid medium before and / or during the culture process. Antibacterial agents or antibiotics (e.g., streptomycin, oxytetracycline) are used to protect the culture from contamination. However, in some embodiments, the metabolic products produced by yeast culture provide sufficient antibacterial effect to prevent contamination of the culture.

[0108] In one embodiment, the components of the liquid culture medium can be optionally sterilized prior to inoculation of the reactor. In one embodiment, sterilization of the liquid growth medium can be achieved by placing the components of the liquid culture medium in water at a temperature of about 85-100° C. In one embodiment, sterilization can be achieved by dissolving the components in 1-3% hydrogen peroxide in a 1:3 (w / v) ratio.

[0109] In one embodiment, the equipment used for culturing is sterile. The culturing equipment, such as the reactor / vessel, may be separate from, but connected to, a sterilization unit, e.g., an autoclave. The culturing equipment may also be equipped with a sterilization unit for in-situ sterilization before inoculation begins. Gaskets, openings, tubes, and other equipment parts may be sprayed with, e.g., isopropyl alcohol. Air may be sterilized by methods known in the art. For example, ambient air may be passed through at least one filter before being introduced into the vessel. In other embodiments, the medium may be pasteurized or, optionally, may not be heated at all, where the use of pH and / or low water activity may be utilized to control the growth of undesirable microorganisms.

[0110] The pH of the culture should be suitable for the microorganism of interest. In some embodiments, the pH is about 2.0 to about 7.0, about 3.0 to about 5.5, about 3.25 to about 4.0, or about 3.5. Buffers and pH adjusters, such as carbonates and phosphates, may be used to stabilize the pH around a preferred value. In some embodiments, a base solution, such as a 15% to 30%, or 20% to 25% NaOH solution, is used to adjust the pH of the culture to a convenient level. The base solution can be included in the growth medium and / or can be fed to the fermentation reactor during the culture to adjust the pH as needed.

[0111] In one embodiment, the culture method is carried out at about 5° C. to about 100° C., about 15° C. to about 60° C., about 20° C. to about 45° C., about 22° C. to about 35° C., or about 24° C. to about 28° C. In one embodiment, the culture may be carried out continuously at a constant temperature. In another embodiment, the culture may be subjected to varying temperatures.

[0112] According to the method, the microorganisms can be cultured in the fermentation system for a period of time sufficient to achieve a desired effect, e.g., a desired amount of cellular biomass or production of a desired amount of SLPs. Microbial growth by-products produced by the microorganisms can be retained within the microorganism and / or secreted into the growth medium. The biomass content can be, for example, 5 g / l to 180 g / l or more, 10 g / l to 150 g / l, or 20 g / l to 100 g / l.

[0113] In certain embodiments, fermentation of the yeast culture occurs for about 40 to 150 hours, or about 48 to 140 hours, or about 72 to 130 hours, or about 96 to 120 hours. In certain embodiments, the fermentation time ranges from 48 to 72 hours, or 96 to 120 hours.

[0114] In some embodiments, the fermentation cycle is terminated when the dextrose and / or oleic acid concentration in the medium is exhausted (e.g., at a level of 0% to 0.5%). In some embodiments, the end of the fermentation cycle is determined to be when the microorganism begins to consume trace amounts of SLPs.

[0115] In some embodiments, production of the SLP molecule "substrate" further comprises post-fermentation modification of the SLP molecules produced in the yeast culture product. In one embodiment, the crude SLP composition is hydrolyzed to produce linear SLPs. In some embodiments, the linear SLPs are deacetylated. In some embodiments, the linear SLPs are peracetylated.

[0116] In some embodiments, the method includes subjecting the crude SLPs to alkaline hydrolysis. For example, in one embodiment, the crude SLPs can be mixed with an equimolar to 1.5 molar solution of a base, e.g., a solution of sodium hydroxide, potassium hydroxide, and / or ammonium hydroxide, to adjust the pH, e.g., to about 4-11, about 5-11, about 6-12, or preferably, about 7-9. In some embodiments, this is accomplished by treating the crude SLPs with a hydroxide salt solution for 2-24 hours, 3-20 hours, or 4-16 hours at elevated temperatures, e.g., 75-100° C., 80-95° C., or 85-90° C.

[0117] According to the method, the lactone bond of lactone-form SLPs is cleaved and converted to crude linear SLPs by a hydrolysis process. In certain embodiments, a portion of the crude linear SLPs is acetylated, diacetylated, or peracetylated, where the portion comprises, for example, 1%-100%, 5%-75%, or 10-50% of the total amount of SLP molecules. In another embodiment, mono- or diacetylated SLP molecules can be deacetylated via the same alkaline hydrolysis process.

[0118] In some embodiments, where bystander cations are or may be present in the hydrolysis process, the crude linear SLPs are purified using a cation exchange resin. More specifically, in preferred embodiments, the crude linear sophorolipids are circulated through an ion exchange bed containing cation exchange sites, e.g., using a peristaltic or other type of pump, for a period of, e.g., 15 minutes to 20 hours, 3 hours to 15 hours, 4 hours to 12 hours, or preferably, 30 minutes to 3 hours.

[0119] The amount of cation exchange sites can be, for example, equimolar to 1.5 molar relative to the concentration of the hydroxide salt used in the alkaline hydrolysis.

[0120] Advantageously, ion exchange resins not only provide a novel method for purifying SLP molecules, but also provide a novel method for neutralizing the pH of the reaction product without the need for standard quenching methods that can dilute and / or alter the chemical composition of the final product.

[0121] In a preferred embodiment, linear SLPs with bystander cations removed serve as standardization substrates for one or more derivatization and / or purification reactions.

[0122] Two-step generation of cationic SLP derivatives via the aldehyde handle After removal of bystander cations, a two-step synthetic scheme can be used to generate reactive aldehyde handles on purified linear SLPs - the first isolated intermediate of the method - and then attach naturally occurring cationic biodegradable functional groups. Sophorolipids, which contain unsaturated bonds at specific positions, allow for site-specific functionalization of SLP molecules.

[0123] Step 1 – Ozonolysis In one embodiment, the purified linear SLPs are transferred to a new clean vessel containing multiple air spargers with large surface area and subjected to ozonolysis. During ozonolysis of the linear SLPs, the olefinic portion of the SLP molecule is converted to an ozonide, which is a reactive five-membered ring.

[0124] In a preferred embodiment, purified linear SLPs are ozone treated with 2-3 vvm of 100% ozone gas for 2-20 hours, 3-16 hours, or 4-10 hours at a temperature preferably at or about -78°C.

[0125] In one exemplary embodiment, the purified linear SLPs are ozonated with 3 vvm of 100% ozone gas for 4 hours, hi another exemplary embodiment, the purified linear SLPs are ozonated with 2 vvm of 100% ozone gas for 16 hours.

[0126] Following ozonolysis, in some embodiments, the SLP-ozonide is degassed with compressed air at 2-3 vvm for 2-20 hours, 3-16 hours, or 4-10 hours.

[0127] In one exemplary embodiment, the SLP-ozonide is degassed with compressed air at 3 vvm for 4 hours. In another exemplary embodiment, the SLP-ozonide is degassed at 2 vvm for 16 hours.

[0128] In a preferred embodiment, the SLP containing ozonide is reduced to obtain an aldehyde handle. After degassing, the SLP-ozonide is reacted with an inorganic reducing agent selected from, for example, triphenylphosphine, sodium borohydride, sodium magnesium bisulfite and sodium metabisulfite. In a preferred embodiment, the reducing agent is triphenylphosphine, which is used at an equimolar concentration relative to the SLP-ozonide. The linear SLP aldehyde is then preferably allowed to return to room temperature.

[0129] Step 2 - Reductive amination In a preferred embodiment, step 2, generating the cationic SLP derivative via the aldehyde handle, involves reductive amination of the linear SLP aldehyde.

[0130] In some embodiments, reductive amination involves the introduction of a primary amine to the aldehyde handle under reducing conditions, generating a stable secondary amine that serves as a covalent linkage between the SLP "scaffold" and the primary amine "cargo."

[0131] First, in some embodiments, the linear SLP aldehyde is extracted from the aqueous mixture with ethyl acetate, concentrated and dried under reduced pressure (e.g., about 200-250 mbar, or about 240 mbar) at a temperature of about 35-45° C. The dried crude linear SLP aldehyde can then be dissolved in a reaction medium comprising tetrahydrofuran (THF) and / or water. The proportion of water used as the reaction medium preferably does not exceed 50% water, typically 0-25%.

[0132] For the amination reaction, a primary amine is introduced to the extracted linear SLP aldehyde along with a reducing agent and a weak organic acid, preferably acetic acid, although other organic acids (e.g., formic acid, trifluoracetic acid) may also be used.

[0133] In some embodiments, the primary amine is a cationic amino acid, such as arginine, lysine or histidine.In some embodiments, the primary amine is a short peptide that contains a repeat of a cationic amino acid.In some embodiments, the primary amine is a short peptide that contains a glycine residue as a spacer between the SLP scaffold and the primary amine cargo and / or between the cationic amino acid residue.

[0134] In certain preferred embodiments, the primary amine is delivered via an amino acid ethyl ester and / or a peptide ethyl ester. In certain embodiments, the reducing agent is sodium cyanoborohydride, sodium triacetoxyborohydride or sodium borohydride.

[0135] In a preferred exemplary embodiment, the reaction uses the amino acid ethyl ester of arginine (Arg) with sodium triacetoxyborohydride as the reducing agent.

[0136] In another exemplary embodiment, the reaction uses the amino acid ethyl esters of histidine (His) or lysine (Lys) with sodium triacetoxyborohydride as the reducing agent.

[0137] In further exemplary embodiments, the peptide ethyl esters are Arg-Arg-Arg-Arg, Gly-Gly-Arg-Arg, Gly-Arg-Gly-Arg, Gly-Arg-Arg-Arg, or other combinations in which individual residues can be substituted from Arg, His, Lys, or glycine (Gly). In some embodiments, the addition of a glycine spacer enhances the water and / or alcohol solubility of the SLP derivative. In some embodiments, the addition of a glycine spacer enhances the antibacterial activity of the SLP derivative, for example, by increasing the chain length of the fatty acid moiety. Advantageously, the chain length can be increased without changing fermentation parameters during the initial production of the linear SLP substrate.

[0138] Additional or alternative chemical transformations to obtain linear sophorolipids containing aldehyde functional groups and secondary amines In certain embodiments, an alternative two-step process utilizing ozonolysis is used to generate linear SLP aldehydes containing secondary amines.

[0139] In some embodiments, hydrolyzed linear SLP substrate serves as starting material. In some embodiments, protecting groups can be attached to all alcohol groups of the SLP sophorose ring. Non-limiting examples of protecting groups include acetyl, trimethylsilyl ether, and tert-butyldiphenylsilyl ether, although many examples of alcohol protecting groups are well known to those skilled in the art.

[0140] In a preferred embodiment, the alkene group of the SLP is converted to an aldehyde moiety without using ozonolysis. Instead, the alkene is epoxidized to an oxirane ring using a peracid reagent (an example of the Prilitsev reaction) or osmium tetroxide. Examples of peracid reagents used according to this method include, but are not limited to, m-chloroperoxybenzoic acid, peroxyacetic acid, and performic acid.

[0141] The resulting epoxide ring is then opened to the vicinal diol, which in some embodiments is accomplished under acid-catalyzed (aqueous) or base-catalyzed (aqueous) conditions.

[0142] Finally, the vicinal diol is oxidatively cleaved to generate an aldehyde group, which can be accomplished by a suitable oxidizing agent such as, for example, sodium periodate.

[0143] After oxidative cleavage of the vicinal diol, the protecting groups, if present, can be removed by conventional methods known for the particular group. For example, silyl ether protecting groups can be removed using an aqueous source of fluoride ions, such as tetrabutylammonium fluoride, because the very strong Si-F bond formed between the silicon and fluorine atoms drives the deprotection reaction to completion.

[0144] Once the aldehyde-containing linear sophorolipid is obtained, it can be converted to the aforementioned derivatized species by the chemical transformations outlined above.

[0145] In certain embodiments, it is desirable to perform chemical transformations to obtain aldehyde functionality while preserving the original alkyl chain length. This can be accomplished in several ways.

[0146] In one embodiment, a two-step synthetic route is used, using lactone-type SLPs as starting material.First, lactone-type SLPs are subjected to alkaline hydrolysis to simultaneously remove acetyl groups while converting free carboxylic acid groups to methyl esters.For example, methyl esters can be converted to aldehyde functional groups using a reducing agent such as DIBAL-H.After obtaining linear sophorolipids containing aldehydes, they can be converted to the aforementioned derivatized species by the chemical transformations outlined above.

[0147] In another embodiment, linear sophorolipids containing aldehydes can be produced by one-step direct reduction of lactone bonds present in lactone-type SLP fermentation products. Under certain conditions, the lactone bonds can be directly reduced to aldehydes in one step, for example, using a complex reducing agent (ate complex) formed between diisobutylaluminum hydride and tert-butyllithium. In addition to ate complexes, other examples of possible reducing agents include, but are not limited to, lithium tri-tertbutoxyaluminum hydride (TBLAH), lithium diisobutyl-tert-butoxyaluminum hydride (LDBBA), and diisobutylaluminum hydride and n-butyllithium ate complexes. After obtaining linear SLPs containing aldehydes, they can be converted to the aforementioned derivatized species by the chemical transformations outlined above.

[0148] Obtaining derivatized SLPs containing short- or long-chain amide functional groups In one embodiment, a linear SLP substrate is fitted with an amide containing cationic amino acid functionality to generate a long chain amide derivative (eg, C18).

[0149] In some embodiments, linear SLP substrates can be converted to short chain amides (e.g., C9) by first cleaving the fatty acid tail via oxidative cleavage and secondly attaching an amide containing a cationic amino acid functionality to the cleaved acid.

[0150] Coupling agents for use in amide attachment according to the present invention may include, for example, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI / HOBt), benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PYBOP), 2-(1H-Benotriazole-1-yl)-1,1,3,3-tetramethylaminium tetrafluorophosphate (TBTU), and / or N,N'-dicyclohexylcarbodiimide / 1-hydroxybenzotriazole (DCC / HOBt). In certain embodiments, the preferred coupling agent is EDCI / HOBt.

[0151] In certain embodiments, linear SLPs containing an aldehyde handle as described above can be converted to long or short chain amides using similar reaction schemes. In some embodiments, the cleaved acid can serve as a substrate for the attachment of the aldehyde handle described above.

[0152] Ion exchange / purification In certain embodiments, the unique cationic nature of the SLP derivatives of the invention allows cationic ion exchange resins to be used for selective purification, e.g., selective retention of cationic species and / or selective removal of unreacted SLPs and SLPs that do not contain the desired carbon chain length or characteristics. Thus, in certain embodiments, the present invention provides novel methods for purifying SLPs and SLP derivatives using cationic ion exchange resins.

[0153] In certain embodiments, following reductive amination, the cationic SLP derivative can be extracted from the reductive amination reaction mixture via standard liquid-liquid extraction with an organic solvent, preferably ethyl acetate, washed with pH 9.0 sodium carbonate buffer, and concentrated under reduced pressure (e.g., about 200-250 mbar, or about 240 mbar). The mixture can then be resuspended in deionized water and purified using a cation exchange resin.

[0154] In certain embodiments, the extracted cationic SLPs are circulated through an ion exchange bed containing an equimolar to 1.5 molar amount of cation exchange sites relative to the concentration of the crude linear cationic SLPs, e.g., using a peristaltic or other type of pump, for a period of 2 to 20 hours, 3 to 15 hours, or 4 to 12 hours.

[0155] In a preferred embodiment, removal of the SLP cationic derivative from the resin is accomplished by application of an electrolyte solution containing a high concentration of monovalent metal cations, where the high concentration is 1.5-15 molar equivalents, or 2-10 molar equivalents relative to the concentration of the SLP cationic derivative. The high concentration of monovalent metal cations outcompetes the bound SLP cationic derivative and can exchange onto the resin, producing a highly purified stream of SLP cationic derivative.

[0156] In some embodiments, following reductive amination, the cationic SLP derivative can be purified by stirring with saturated ammonium chloride solution to produce a stirred mixture; extracting the cationic SLP derivative by applying CHCl solvent (3x) to the stirred mixture to produce an extraction mixture; removing traces of water from the extraction mixture by applying MgSO or NaSO; drying the extraction mixture under high pressure (e.g., 350-450 mbar, or 400 mbar) and at 35-45° C. to remove CHCl solvent; and applying 21% NaOEt / EtOH solution, NaHCO or KHCO base in ethanol to remove the acetyl R group from the cationic SLP derivative. The deacetylated linear cationic SLP derivative can then be converted to the HCl salt by reaction with 1.25 M HCl / EtOH solution.

Claims

1. 1. A conditioning composition comprising a cationic sophorolipid (SLP) molecule that has been derivatized to have one of the following formulas: where R = arginine, lysine, or histidine, or a peptide containing repeats thereof, and R 1 = H, acetyl, butyl, or isobutyl, The conditioning composition.

2. 10. The composition of claim 1, further comprising an underivatized SLP molecule.

3. 3. The composition of claim 2, wherein the ratio of cationic derivatized SLPs to underivatized SLPs is from 1:10 to 1:1000.

4. 10. The composition of claim 1, further comprising mannosylerythritol lipid (MEL).

5. 5. The composition of claim 4, wherein the ratio of said cationic derivatized SLPs to MEL is from 1:10 to 1:1000.

6. 5. The composition of claim 4, wherein the ratio of said cationic derivatized SLPs to MEL is from 1000:1 to 10:

1.

7. Carriers, organic and / or inorganic solvents, organic and / or inorganic acids, essential oils, plant extracts, crosslinkers, chelating agents, fatty acids, alcohols, pH adjusters, reducing agents, buffers, enzymes, dyes, colorants, fragrances, preservatives, emulsifiers, demulsifiers, foaming agents, anti-foaming agents, bleaching agents, emollients, humectants, anti-inflammatory agents, polymers, stabilizers, silicones, thickeners, emollients, UV blockers, moisturizers, film formers, minerals, vitamins, proteins, viscosity and / or rheology modifiers, insect repellents, skin cooling compounds, skin protectants, lubricants, pearls, 10. The composition of claim 1, further comprising one or more other ingredients selected from the group consisting of chromalite, mica, antiallergic agents, antibacterial agents, antifungal agents, antiviral agents, antibacterial agents, preservatives, pharmaceuticals, light stabilizers, surface smoothers, optical diffusers, exfoliation enhancers, antistatic agents, anti-wrinkle agents, humectants, dye transfer aids, color protectants, deodorizers, odor traps, detergents, drying agents, water repellents, anti-pilling agents, acidulants, sizing agents, optical brighteners, antioxidants, shrinkage control agents, starches, and mixtures thereof.

8. 10. The composition of claim 1, which is formulated as a liquid; a colloidal dispersion; a microemulsion or nanoemulsion; a gel; a serum; a granular, spray-dried or dry-blend powder; a solid bar; a concentrate; an encapsulated dissolvable pod; a suspension; a hydrogel; a multiphase solution; a vesicular dispersion; a foam; a mousse; a spray; an aerosol; a liquid cake; an ointment; an essence; a paste; a tablet; a water-soluble sheet or sachet; and / or is capable of being impregnated into a dry or wet substrate such as a sheet, ball, cloth, sponge or wipe.

9. 1. A method for conditioning hair, fibers, or textiles, the method comprising contacting the hair, fibers, or textiles with a conditioning composition comprising a cationic derivatized sophorolipid (SLP) molecule for an amount of time effective to achieve a desired level of conditioning, wherein the derivatized SLP molecule has the following formula: and where R = arginine, lysine, glycine, or histidine, or a peptide containing repeats thereof, and R 1 = H, acetyl, butyl, or isobutyl, The method.

10. 10. The method of claim 9, further comprising contacting the hair, fiber, or textile with underivatized SLP molecules.

11. 11. The method of claim 10, wherein the ratio of derivatized cationic SLPs to underivatized SLPs is from 1:10 to 1:1000.

12. 10. The method of claim 9, further comprising contacting the hair, fiber or textile with mannosylerythritol lipid (MEL).

13. 13. The method of claim 12, wherein the ratio of derivatized cationic SLPs to MEL is between 1:10 and 1:1000.

14. 13. The method of claim 12, wherein the ratio of derivatized cationic SLPs to MEL is between 1000:1 and 10:

1.

15. The conditioning composition may comprise a carrier, organic and / or inorganic solvent, organic and / or inorganic acid, essential oil, botanical extract, crosslinker, chelating agent, fatty acid, alcohol, pH adjuster, reducing agent, buffer, enzyme, dye, colorant, fragrance, preservative, emulsifier, demulsifier, foaming agent, anti-foaming agent, bleach, emollient, humectant, anti-inflammatory agent, polymer, stabilizer, silicone, thickener, emollient, UV blocker, moisturizer, film former, mineral, vitamin, protein, viscosity and / or rheology modifier, insect repellent, skin cooling compound.

10. The method of claim 9, further comprising one or more other ingredients selected from the group consisting of skin protectants, lubricants, pearls, chromalite, mica, antiallergic agents, antibacterial agents, antifungal agents, antiviral agents, antibacterial agents, preservatives, pharmaceuticals, light stabilizers, surface smoothers, optical diffusers, exfoliation enhancers, antistatic agents, anti-wrinkle agents, humectants, dye transfer aids, color protectants, deodorizers, odor traps, detergents, drying agents, water repellents, anti-pilling agents, acidulants, sizing agents, optical brighteners, antioxidants, shrinkage control agents, starches, and mixtures thereof.

16. 10. The method of claim 9, wherein after an effective amount of contact time to achieve conditioning, the conditioning composition is rinsed from the hair, fiber, or textile with water or a solvent.

17. 10. The method of claim 9, wherein the conditioning composition is left on the hair, fibers, or textiles as a leave-in conditioner.

18. The following benefits: reducing static and / or frizz; increasing strength; reducing breakage; reducing tangling and matting; improving shine and softness; increasing oil and / or moisture retention; reducing wrinkles; and / or imparting fragrance 10. The method of claim 9, wherein one or more of the following is applied to the hair, fiber or textile.

19. 10. A method of conditioning hair, fibers or textiles, comprising contacting said hair, fibers or textiles with the composition of any one of claims 1 to 9.

20. 20. The method of claim 19, further comprising rinsing the composition from the hair, fibers or textiles with water or a solvent.

21. 20. The method of claim 19, wherein the conditioning composition is left on the hair, fibers, or textiles as a leave-in conditioner.

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