Modified sophorolipids for conditioning hair and textiles

Abstract

The present invention provides a conditioning composition for hair, fibers and textiles, wherein the conditioning composition comprises a derived cationic biosurfactant.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to U.S. Provisional Patent Application No. 63 / 314,757, filed on February 28, 2022, which is incorporated herein by reference in its entirety. Background Art

[0003] Consumers use and come into contact with household and personal care products every day. For example, most consumers' daily routines include the use of hair care products, cosmetics, cleaners, laundry detergents, etc. Although many of these types of products contain irritating chemicals as active ingredients, additional chemicals may be included as additives that, for example, aid in the properties of fragrances, dyes, and active ingredients such as viscosity, foaming, and solubility.

[0004] One specific category of products of interest is hair care products. Washing hair with shampoo cleanses the hair by removing excess environmental soil and sebum. Washing with shampoo may also cause the hair to become tangled and unmanageable, especially for longer hair. Furthermore, once the hair is dry, it is often left dry, rough, static-y, dull, and / or frizzy because the hair's natural oils and other natural conditioning and moisturizing components are removed.

[0005] To avoid these problems, hair conditioning compositions are typically applied to the hair immediately after washing and rinsing with a shampoo. The conditioning composition is worked throughout the hair and can then be used as a leave-in conditioner, or it can be rinsed from the hair with water. Similar types of compositions have also been used to condition textiles and fibers.

[0006] Traditionally, hair and fiber conditioning compositions have used cationic surfactants. Cationic surfactants are those in which the surfactant activity resides in the positively charged cationic portion of the molecule. Thus, cationic surfactants are attracted to the negatively charged surface of hair or fiber and deposit on the hair or fiber. Among cationic surfactants, quaternary ammonium compounds (QACs) are particularly suitable for treating hair and fiber. 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.

[0007] Toxicity to humans and livestock is a short-term problem for existing personal care and household products. The environmental damage that may be attributed to these ingredients is not yet fully understood; however, it is largely dose-dependent. In some cases, QACs have been shown to persist in the environment. Although biodegradation pathways have been shown under laboratory aerobic conditions, QACs, especially those containing aromatic scaffolds, tend to accumulate in environmental sludge and are insufficiently distributed into aqueous media. This removes QACs from aerobic environments where biodegradation may occur. The accumulation of QACs in anaerobic environmental sludge and soil poses a major challenge. Typical methods for removing other nitrogen-containing environmental pollutants (whether natural or caused by human activities) are severely limited by the presence of QACs.

[0008] It is possible that QACs biodegrade in anaerobic sludge environments, but the main decomposition products of QACs include short alkylamines such as methylamine. Alkylamines can accumulate in microorganisms that can degrade QACs, leading to inhibition of QAC-degrading enzymes and / or toxicity to the microorganisms themselves. Further complicating the issue is that QACs have been shown to inhibit methanogenesis and other anaerobic digestion pathways used by microorganisms to degrade other compounds. Therefore, the risk of QACs in the environment raises the risk of accumulation of other hazardous chemicals that would normally degrade.

[0009] In addition to the problem of QAC accumulation in the environment and its impact on microorganisms necessary for biodegradation pathways, recent studies have shown that QAC environmental accumulation is also fueling the development of microorganisms that are resistant to traditional antibiotics. The same genes found to be responsible for conferring QAC resistance in bacteria are associated with resistant bacteria studied by medical researchers. This resistance mechanism involves the use of efflux proteins that have broad specificity for exogenous compounds. Therefore, the use and environmental accumulation of QACs will cause selection of bacteria that can resist them and inadvertently may resist traditional antibiotics.

[0010] There are a variety of naturally derived materials that have shown some efficacy as conditioning ingredients. One such material is palm oil and its derivatives (e.g., palmitate, glyceryl, stearic acid, sodium laureth sulfate, sodium lauryl sulfate). In shampoos and conditioners, palm oil is used to help restore the hair's natural oils that are stripped away by the other cleaning chemicals present in most shampoos.

[0011] While palm oil production and harvesting is considered economically cheap, the environmental costs are becoming increasingly concerning. Massive palm oil production is causing rainforest destruction, endangerment of native species, and water pollution due to improper treatment of processing wastewater.

[0012] More and more consumers are seeking household and personal care products that are non-toxic, non-irritating to the skin and / or eyes, and have a reduced environmental impact, but these safer and more sustainable products are still expected to perform on par with conventional products on many attributes, such as conditioning of the hair and fibers. Formulating safe and environmentally friendly conditioning compositions remains a challenge due to the limited set of natural or sustainable materials that meet these demands.

[0013]

[0006] Therefore, there is a need for improved compositions that effectively impart the benefits of traditional conditioners to hair and textiles without the presence of harmful or polluting chemicals or synthetically derived ingredients. Summary of the invention

[0014] The present invention provides microbial-based products and methods of use thereof in hair, fiber and textile conditioning. More specifically, the present invention provides microbial-derived ingredients for formulating hair care products, household laundry products and textile processing materials. Advantageously, in certain embodiments, microbial-derived ingredients can be used to replace and / or reduce the use of traditional conditioning compounds such as QAC and palm oil.

[0015] In preferred embodiments, the present invention provides microbially derived surfactants or biosurfactants for use in conditioning formulations for hair, laundry, and textile fibers. In certain specific embodiments, the biosurfactants have been derivatized and / or purified to produce and / or enhance one or more desired functions, preferably conditioning functions.

[0016] In certain embodiments, conditioning functions include one or more of the following non-limiting examples: reducing static and / or frizz; increasing strength; reducing breakage; reducing tangles and mattiness; improving shine and softness; increasing oil and / or water retention; reducing wrinkles; and / or imparting fragrance.

[0017] In certain embodiments, the biosurfactant is a glycolipid selected from, for example, sophorolipids (SLPs), mannoerythritol lipids (MELs), rhamnolipids (RLPs), and trehalolipids (TLs).

[0018] In certain specific embodiments, the biosurfactant comprises a mixture of sophorolipids or SLP molecules, wherein the SLP molecules include, for example, lactone SLPs, linear SLPs, deacetylated SLPs, monoacetylated SLPs, diacetylated SLPs, esterified SLPs, SLPs with different hydrophobic chain lengths, SLPs attached with fatty acid-amino acid complexes, etc., including those SLPs specifically exemplified and / or not specifically exemplified in the present disclosure.

[0019] In a specific preferred embodiment, the biosurfactant is a derivatized SLP or a mixture of derivatized SLPs, wherein the molecular structure of the SLP molecule has been altered to produce a linear (acidic) cationic SLP derivative. More specifically, in a preferred embodiment, the linear cationic SLP derivative has been altered to contain cationic amino acid residues, such as arginine, lysine or histidine; a peptide containing a repeating sequence of arginine, lysine and / or histidine; or a peptide containing a glycine spacer between individual amino acids and / or between the SLP scaffold and the amino acid or peptide residues.

[0020] 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, such compositions and such methods are at least as effective conditioners as QACs and other synthetic cationic conditioning ingredients and palm oil.

[0021] In certain specific embodiments, the conditioning composition may also include additional biosurfactants. For example, in some embodiments, the conditioning composition comprises a derivatized linear cationic SLP according to the present invention and one or more other underivatized SLP molecules. 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.

[0022] Optionally, the conditioning composition may also contain one or more other components, including, for example, carriers (e.g., water), solvents, organic and / or inorganic acids, essential oils, plant extracts, cross-linking agents, chelating agents, fatty acids, alcohols, pH adjusters, reducing agents, buffers, enzymes, dyes, colorants, fragrances, preservatives, emulsifiers, foaming agents, bleaching agents, polymers, thickeners and / or viscosity regulators.

[0023] In some embodiments, the conditioning composition can be used in hair care products such as shampoos, conditioners or cream rinses, de-tanglers, 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 treatments to condition raw fibers or raw fabrics prior to assembling garments, rugs, and other textiles.

[0024] In a preferred embodiment, the present invention also provides a method for conditioning hair, fiber or textile, wherein the method comprises contacting the conditioning composition of the present invention with the hair, fiber or textile for an amount of time sufficient 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, fiber or textile after contact therewith, while in other embodiments, the composition is left in place without being rinsed.

[0025] Advantageously, the method of the present invention is safe to use in, for example, domestic, commercial, healthcare and industrial environments and in the presence of humans, plants and animals. In addition, the conditioning compositions of the present invention can be produced and used without causing harm to the user and without releasing large amounts of pollution and toxic compounds into the environment. In addition, the compositions and methods utilize biodegradable and toxicologically safe components. Therefore, the present invention can be used in a variety of industries as a "green" conditioning ingredient. DETAILED DESCRIPTION

[0026] The present invention provides microbial-based products and methods of use thereof in hair, fiber and textile conditioning. More specifically, the present invention provides microbial-derived ingredients for formulating hair care products, household laundry products and textile processing materials. Advantageously, in certain embodiments, microbial-derived ingredients can be used to replace and / or reduce the use of traditional conditioning compounds such as QAC and palm oil.

[0027] In a preferred embodiment, the invention provides microbial derived surfactants or biosurfactants in conditioning formulations for hair, laundry and textile fibers. Biosurfactants are amphiphilic molecules consisting of a hydrophobic domain (e.g., fatty acid) and a hydrophilic domain (e.g., sugar). Because biosurfactants have amphiphilic properties, they can be distributed at interfaces between different fluid phases, such as oil / water or water / air interfaces. Unlike synthetic surfactants, biosurfactants can be effective in hot or cold water and at any extreme value of the pH scale. In addition, biosurfactants are biodegradable and nontoxic.

[0028] In particular, glycolipid biosurfactants have many important physiological roles in cell biology, primarily as major components of cell membranes; however, they have gained attention in recent years due to their potential to serve as bioreplacements for discontinued surfactants.

[0029] In certain embodiments of the present invention, sophorolipids (SLPs) are specific glycolipids of interest. Sophorolipids are glycolipid biosurfactants produced by various yeasts of, for example, Starmerella clades. SLPs consist of disaccharide sophoroses connected to long-chain hydroxy fatty acids. They can include partially acetylated 2-O-β-D-pyranose glucopyranose units connected to 17-L-hydroxyoctadecanoic acid or 17-L-hydroxy-Δ9-octadecenoic acid with β-glycosides. Hydroxy fatty acids can have, for example, 11 to 20 carbon atoms and can contain one or more unsaturated bonds. In addition, the sophorose residue can be acetylated at the 6-position and / or 6'position. The fatty acid carboxyl group can be free (acidic or linear form) or internally esterified (lactone form) at the 4" position. In most cases, SLP fermentation produces 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, non-acetylated linear SLPs).

[0030] As used herein, the term "sophorolipid", "sophorolipid molecule", "SLP" or "SLP molecule" includes all forms of SLP molecules and isomers thereof, including, for example, acidic (linear) SLP and lactone SLP. Also included are monoacetylated SLP, diacetylated SLP, esterified SLP, SLP with different hydrophobic chain lengths, SLP attached with fatty acid-amino acid complexes, etc., including those SLPs described and / or not described in the present disclosure.

[0031] In some embodiments, the SLP molecule can be represented by the general formula (1) and / or the general formula (2), and ... 3 ) and in some cases in R 1 and / or R 2 A collection of 30 or more types of structural homologues with acetylation or protonation was obtained.

[0032]

[0033] In the general formula (1) or (2), R 0 It can be a hydrogen atom or a methyl group. 1 and R 2 Each is independently a hydrogen atom or an acetyl group. 3 It is a saturated aliphatic hydrocarbon chain or an unsaturated aliphatic hydrocarbon chain having at least one double bond, and may have one or more substituents.

[0034] Non-limiting examples of substituents include halogen atoms, hydroxyl groups, lower (C1-6) alkyl groups, halogenated lower (C1-6) alkyl groups, hydroxy lower (C1-6) alkyl groups, halogenated lower (C1-6) alkoxy groups, and the like, such as those described in the present disclosure. 3 It may have, for example, 11 to 20 carbon atoms.

[0035] Fermentation of yeast cells in a culture substrate comprising sugars and / or lipids and fatty acids with carbon chains of varying lengths can be used to produce a variety of SLPs. The yeast Bombus spp. (Candida) is one of the most widely recognized SLP producers. In general, yeast produces both lactone SLPs and linear SLPs during fermentation, wherein about 60%-70% of the SLPs comprise the lactone form and the remainder comprises the lactone form.

[0036] Selected Definitions

[0037] As used herein, the term "conditioning" as applied 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 mattness; improving shine and softness; increasing oil and / or water retention; reducing wrinkles; and / or imparting fragrance.

[0038] As used herein, "dermatologically acceptable", "cosmetically acceptable", and "topically acceptable" are used interchangeably and are intended to mean that the particular components are safe and non-toxic for application to the integument (e.g., skin, scalp) at the levels employed. In one embodiment, the components of the composition are considered to be Generally Recognized as Safe (GRAS).

[0039] As used herein, the term "effective amount" refers to an amount of something (e.g., compound, composition, time) that is capable of achieving the desired amount of conditioning in hair, fibers, and / or textiles. The actual amount will vary depending on many factors, including but not limited to the amount of conditioning required, the type of hair, fibers, and / or textiles, and the mode of application.

[0040] As used herein, "microbial-based compositions" means compositions that include components produced by the growth of microorganisms or other cell cultures. Thus, microbial-based compositions may include the microorganisms themselves and / or microbial growth byproducts (e.g., biosurfactants, solvents, and / or enzymes). Cells may be in a vegetative state or in spore form, or both. Cells may be planktonic or in biofilm form, or both. Cells may be alive or inactive, intact or lysed. Cells may be removed from the medium in which they were grown, or at least 1×10 3 , 1×10 4 , 1×10 5, 1×10 6 , 1×10 7 , 1×10 8 , 1×10 9 , 1×10 10 or 1×10 11 In one embodiment, the composition based on a microorganism may only contain a culture medium in which the cells have been grown, wherein the cells have been removed (but in some cases, some residual cell material may also be retained in the culture medium). Growth byproducts may be present in the culture medium and may include, for example, metabolites, cell membrane components, expressed proteins, and / or other cellular components. In one embodiment, the composition based on a microorganism only contains microbial growth byproducts.

[0041] The present invention further provides "microorganism-based products", which are products that are applied in practice to achieve desired results. Microorganism-based products can be simply microorganism-based compositions harvested from microorganism culture processes. Alternatively, microorganism-based products can contain additional ingredients that have been added. These additional ingredients can include, for example, stabilizers, buffers, carriers, and other additives and / or adjuvants suitable for specific applications. Microorganism-based products can also contain mixtures of microorganism-based compositions. Microorganism-based products can also contain one or more components of microorganism-based compositions that have been treated in some way, such as but not limited to filtration, centrifugation, lysis, drying, purification, etc.

[0042] "Metabolite" refers to any substance produced by metabolism (e.g., growth byproducts) or a substance necessary to participate in a specific metabolic process. Examples of metabolites include, but are not limited to, enzymes, acids, solvents, alcohols, proteins, carbohydrates, vitamins, minerals, trace elements, amino acids, polymers, and biosurfactants.

[0043] As used herein, the term "isolated" or "purified" when used in connection with biological or natural materials, such as nucleic acid molecules, polynucleotides, polypeptides, proteins, organic compounds such as small molecules, microbial cells / strains or host cells, means that the material is substantially free of other compounds with which it is associated in nature, such as cellular material. That is, the material does not occur naturally without these other compounds and / or has different or unique characteristics compared to those found in the natural material.

[0044] In certain embodiments, the purified compound is at least 60% by weight of the compound of interest. Preferably, the preparation is at least 75% (w / w), more preferably at least 90% (w / w), and most preferably at least 99% (w / w) or 100% (w / w) of the desired compound by weight. Purity is measured by any appropriate standard method, such as by column chromatography, thin layer chromatography, or high performance liquid chromatography (HPLC) analysis.

[0045] 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 positions; and stereoisomers (stereoisomers), in which the bond structure is the same, but the geometric positioning of atoms and functional groups in space is different. MEL isomers can differ in the bond type and bond position of carbohydrates, fatty acids and / or acetyl groups, for example.

[0046] As used herein, the term "subject" refers to an animal, preferably a mammal. In the context of the present invention, the preferred subject is a human. The subject can be of any gender and any age or development stage, including infants, young children, adolescents, teenagers, young adults, middle-aged people or the elderly.

[0047] As used herein, "surfactant" means a surface-active substance or a compound that reduces the surface tension (or interfacial tension) between two phases. Surfactants are used, for example, as detergents, wetting agents, emulsifiers, foaming agents and / or dispersants. "Biosurfactant" means a surfactant produced by a living organism and / or produced using naturally derived substrates.

[0048] Generally speaking, "textiles" refers to any flexible material produced by interweaving yarns or wire bundles, such as fabrics, cloths or carpets, which are produced by spinning fibrils into long and plied lengths. Interweaving can be achieved via, for example, braiding, knitting, crocheting, knotting, weaving, felting, bonding or plaiting. In addition to flexible materials, "textiles" as used herein can also include finished products produced using flexible materials and raw materials involved in the production of flexible materials, including fibrils, raw yarns and raw wire bundles. In certain embodiments, finished textiles include clothes, furniture decorations, curtains, carpets and small rugs. In certain embodiments, textiles can also include paper products.

[0049] Textiles can be made from, for example, protein-rich sources (e.g., wool, silk, hair, fur), cellulose-rich sources (e.g., cotton, flax, hemp, coconut, wood and other plants), mineral sources (e.g., asbestos), and synthetic sources (e.g., polyamines, polyesters, acrylonitrile, polyurethanes and other polymers).

[0050] As used herein, "topical" means topical application suitable for external use on the skin, scalp or hair. In other words, the topical composition is not intended for administration to a subject by oral, intravenous, intramuscular, intrathecal, subcutaneous, sublingual, buccal, rectal, vaginal, inhalation, ocular or otic routes.

[0051] 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 any element, step, or ingredient not specified in the claim. The transitional phrase "consisting essentially of" limits the scope of a claim to the specified materials or steps "and those that do not materially affect the basic and novel characteristics of the claimed invention." Use of the term "comprising" contemplates other embodiments of "consisting of" or "consisting essentially of the recited components."

[0052] Unless specifically stated or obvious from the context, the term "or" as used herein is understood to be inclusive. Unless specifically stated or obvious from the context, the terms "a / an" and "the" as used herein are understood to be singular or plural.

[0053] Unless specifically stated or obvious from the context, the term "about" as used herein is understood to be within the normal tolerance range of the art, such as within 2 standard deviations of the mean. "About" can be understood to be within 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1%, 0.5%, 0.1%, 0.05% or 0.01% of the specified value.

[0054] The recitation of a list of chemical groups in any definition of a variable herein includes definitions of the variable as any single group or combination of the listed groups. The recitation of an embodiment of a variable or aspect herein includes the embodiment as any single embodiment or in combination with any other embodiment or portion thereof.

[0055] Any composition or method provided herein can be combined with one or more of any other composition and method provided herein. Other features and advantages of the present invention will be apparent from the following description of preferred embodiments of the present invention and the claims. All references cited herein are incorporated herein by reference.

[0056] Conditioning composition

[0057] The present invention provides microbial-based products and methods of use thereof in hair, fiber and textile conditioning. More specifically, the present invention provides microbial-derived ingredients for formulating hair care products, household laundry products and textile processing materials. Advantageously, in certain embodiments, microbial-derived ingredients can be used to replace and / or reduce the use of traditional conditioning compounds such as QAC and palm oil.

[0058] In some embodiments, the conditioning composition can be used in hair care products such as shampoos, conditioners or nourishing lotions, detangling lotions 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 treatments to condition raw fibers or raw fabrics prior to assembling garments, rugs, and other textiles.

[0059] In preferred embodiments, the present invention provides microbially derived surfactants or biosurfactants for use in conditioning formulations for hair, laundry, and textile fibers. In certain specific embodiments, the biosurfactants have been derivatized and / or purified to produce and / or enhance one or more desired functions, preferably conditioning functions.

[0060] In certain embodiments, the biosurfactant is a glycolipid selected from, for example, sophorolipids (SLPs), mannoerythritol lipids (MELs), rhamnolipids (RLPs), and trehalolipids (TLs).

[0061] In some embodiments, the biosurfactant is used in a crude form, wherein the biosurfactant molecules are present in a growth medium (e.g., a culture broth) in which the microorganism producing the biosurfactant is cultured and collected from the culture medium without purification. The crude form may contain, for example, at least 0.001%, 1%, 5%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or 99% of the amphiphilic molecules in the growth medium. In alternative embodiments, the biosurfactant is extracted from the growth medium and optionally derivatized and / or purified.

[0062] In certain specific embodiments, the biosurfactant comprises a mixture of sophorolipids or SLP molecules, wherein the SLP molecules include, for example, lactone SLPs, linear SLPs, deacetylated SLPs, monoacetylated SLPs, diacetylated SLPs, esterified SLPs, SLPs with different hydrophobic chain lengths, SLPs attached with fatty acid-amino acid complexes, etc., including those SLPs specifically exemplified and / or not specifically exemplified in the present disclosure.

[0063] In a specific preferred embodiment, the biosurfactant is a derivatized SLP or a mixture of derivatized SLPs, wherein the molecular structure of the SLP molecule has been altered to produce a linear (acidic) cationic SLP derivative. More specifically, in a preferred embodiment, the linear cationic SLP derivative has been altered to contain cationic amino acid residues, such as arginine, lysine or histidine; a peptide containing a repeating sequence of arginine, lysine and / or histidine; or a peptide containing a glycine spacer between individual amino acids and / or between the SLP scaffold and the amino acid or peptide residues.

[0064] In certain embodiments, the derived SLP has a formula according to formula (3), (4), (5) or (6), wherein R = lysine, histidine, glycine, arginine or a peptide comprising a repeating sequence of lysine, histidine and / or arginine, and R1 = H, acetyl, butyl or isobutyl.

[0065]

[0066]

[0067] In certain embodiments, the conditioning composition comprises a derivatized SLP of formula (3)-(6) at a dosage rate of about 100 ppm to about 250,000 ppm, about 200 ppm to about 100,000 ppm, about 300 ppm to about 75,000 ppm, about 400 ppm to about 50,000 ppm, or about 500 ppm to about 25,000 ppm.

[0068] In certain embodiments, the conditioning composition comprises 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 % of the derivatized SLP.

[0069] In certain specific embodiments, the conditioning composition may also include additional biosurfactants.For example, in some embodiments, the conditioning composition includes a derivatized linear cationic SLP according to the present invention and one or more other underivatized SLP molecules.

[0070] The mixing ratio of the cationically derivatized SLP to the underivatized SLP may be in the range of 1:1 to 1:1000, 1:5 to 1:500, or 1:10 to 1:100.

[0071] In other embodiments, conditioning compositions comprise a derivatized linear cationic SLP and one or more mannoerythritol lipid (MEL) molecules.

[0072] The mixing ratio of the cation-derivatized SLP to the MEL may be in the range of 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.

[0073] In yet another exemplary embodiment, a conditioning composition comprises a derivatized linear cationic SLP, one or more other SLP molecules, and one or more MEL molecules.

[0074] In one embodiment, MEL comprises 4-OBD-pyranosyl-mesoerythritol or 1-OBD-pyranosyl-mesoerythritol as the hydrophilic part and fatty acid group and / or acetyl group as the hydrophobic part.Usually one or two hydroxyl groups at C4 and / or C6 of mannose residue can be acetylated.In addition, one to three chain lengths can be present for esterified fatty acids of 8 to 12 carbons or more carbons.

[0075] MEL and MEL-like substances (e.g., mannose-based substances) are produced primarily by Pseudozyma spp. (e.g., P. aphidis) and Ustilago spp. (e.g., U. maydis), and there is considerable variability in the structure of the MEL produced by each species. Certain mannose-based substances with properties similar to MEL can also be produced by Meyerozyma guilliermondii.

[0076] MEL is non-toxic and stable over a wide range of temperature and pH. In addition, MEL can be used without any additional preservatives.

[0077] MEL can be produced in over 93 different combinations, which are divided into 5 categories: MEL A, MEL B, MELD, triacetylated MEL A and triacetylated MEL B / C. These molecules can be modified, either synthetically or naturally. For example, MEL can contain different carbon chain lengths or different numbers of acetyl and / or fatty acid groups.

[0078] The MEL molecules of the present invention and / or their modified forms may include, for example, triacylated, diacylated, monoacylated, triacetylated, diacetylated, monoacetylated and non-acetylated MEL and their stereoisomers and / or structural isomers.

[0079] According to the present invention, other mannose-based substances / MEL-like substances exhibiting similar structures and similar properties, such as mannosyl-mannitol lipids (MML), mannosyl-arabinitol lipids (MAL) and / or mannosyl-ribitol lipids (MRL) may also be used.

[0080] In certain embodiments, the composition comprises a carrier. Non-limiting examples of carriers may include, for example, water; saline; saline; ointments; creams; oil-water emulsions; water-in-oil emulsions; silicone-in-water emulsions; water-in-silicone emulsions; wax-in-water emulsions; water-oil-water triple emulsions; microemulsions; gels; vegetable oils; mineral oils; ester oils such as octyl palmitate, isopropyl myristate, and isopropyl palmitate; ethers such as dioctyl ether and dimethyl isosorbide; alcohols such as ethanol and isopropanol; fatty alcohols such as cetyl alcohol, cetearyl alcohol, stearyl alcohol, and behenyl alcohol; isoparaffins such as isooctane, isododecane (IDD), and isobutylene glycol. Hexadecane; silicone oils such as cyclomethicone, dimethicone, dimethicone crosspolymers, polysiloxanes and their derivatives, preferably organically modified derivatives, including PDMS, dimethicone copolyols, dimethicone alcohol and aminodimethicone alcohol; hydrocarbon oils such as mineral oil, petrolatum, isoeicosane and polyolefins (e.g. (hydrogenated) polyisobutylene); polyols such as propylene glycol, glycerol, butylene glycol, pentylene glycol, hexylene glycol, caprylyl glycol; waxes such as beeswax, carnauba wax, ozokerite, microcrystalline wax, polyethylene wax and vegetable wax; or any combination or mixture of the foregoing. The aqueous vehicle may include one or more water-miscible solvents, including lower alcohols such as ethanol, isopropanol, etc. The vehicle may account for about 1% to about 99%, 10% to about 85%, 25% to 75%, or 50% to about 65% by weight of the composition.

[0081] Optionally, the conditioning composition may also contain one or more other components relevant to the specific use, including, for example, organic and / or inorganic solvents, organic and / or inorganic acids, essential oils, plant extracts, crosslinking agents, 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 blockers, moisturizers, film formers, minerals, vitamins, proteins, viscosity regulators. and / or rheology modifiers, insect repellents, skin cooling compounds, skin protectants, lubricants, pearls, chromalite, mica, antiallergic agents, antimicrobial agents (e.g., antifungal agents, antiviral agents, antibacterial agents), bactericides, pharmaceutical agents, light stabilizers, surface smoothing agents, optical diffusers, exfoliation accelerators, antistatic agents, anti-wrinkle agents, wetting agents, dye transfer aids, color protectants, deodorants, odor traps, detergents, drying agents, water repellents, anti-pilling agents, acidulants, starch agents, optical brighteners, antioxidants, shrinkage control agents, starch, and mixtures thereof.

[0082] The amount of each ingredient, whether active or inactive, is that which is conventionally used in cosmetics / personal care, textile processing, and laundry care to achieve its intended purpose, and is generally in the range of about 0.0001% to about 25% or about 0.001% to about 20% of the composition, although such amounts may fall outside these ranges. The nature of these ingredients and their amounts must be compatible with the production and function of the compositions of the present disclosure. In a preferred embodiment, the composition comprises additives that are considered dermatologically acceptable.

[0083] In certain embodiments, the composition may include a pH adjusting agent (e.g., citric acid, ethanolamine, sodium hydroxide, etc.) to be formulated within a wide range of pH levels. In one embodiment, the pH of the conditioning composition is in the range of 1.0 to 13.0. In some embodiments, the pH of the conditioning composition is in the range of 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.

[0084] The present invention may take any number of forms. These forms may include, for example, liquids; colloidal dispersions; micro- or nanoemulsions; gels; serums; granular powders, spray-dried powders or dry-blended powders; solid bars; concentrates; encapsulated soluble pods; suspensions; hydrogels; multiphase solutions; vesicular dispersions; foams; mousses; sprays; aerosols; liquid cakes; ointments; essences; pastes; tablets; water-soluble tablets or pouches; and / or can be impregnated into dry or pre-moistened substrates such as sheets (e.g., dryer sheets), balls (e.g., wool dryer balls), cloths, sponges, or wipes.

[0085] Methods of conditioning hair, fibers and textiles

[0086] In a preferred embodiment, the present invention also provides a method for conditioning hair, fibers or textiles, wherein the method comprises contacting the conditioning composition of the present invention with the hair, fibers or textiles 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 and textiles after contacting it with the hair, fibers and textiles.

[0087] In the case of a hair conditioner, such methods may include contacting the hair with the composition. In some embodiments, the composition is contacted with the hair while the hair is wet, while in other embodiments, the hair is dry. Application may include lathering the composition into the hair tress or rubbing the composition into the hair tress; spraying the composition onto the hair; combing the composition throughout the hair; and / or other standard modes of application for hair care products.

[0088] In certain embodiments, the composition is applied to the hair while shampooing the hair or after shampooing the hair (i.e., after cleaning and rinsing the hair). The conditioning composition can be left in the hair as a leave-in conditioning treatment, or the composition can be rinsed off after, for example, at least 15 seconds, at least 30 seconds, at least 1 minute, at least 5 minutes to at least 60 minutes of contact.

[0089] In the case of fiber conditioners, the composition can be contacted with fibers used to assemble garments and other textiles. In certain embodiments, the fibers are contacted with the composition before being assembled into textiles.

[0090] Chemical surfactants are often used to flush or clean raw fibers prior to further processing. Because flushing can dry out the fibers, conditioning or lubrication is necessary before the fibers are spun, roped, and woven into textiles. Thus, in certain embodiments, a conditioning composition may be contacted with the fibers to lubricate and soften the fibers, thereby reducing breakage, dryness, static electricity, and / or stiffness after flushing.

[0091] In the case of textile conditioning, the methods of the present invention can be used during the finishing stage of textile manufacturing as well as in domestic and industrial laundry. For example, in some embodiments, the conditioning composition is used in the form of a fabric softener that is applied to clothing and other textiles during a standard wash cycle, during a drying cycle, or as a spray applied to wet or dry textiles.

[0092] Production of derivatized cationic SLP molecules

[0093] The present invention provides materials and methods for producing, derivatizing and purifying sophorolipids (SLPs). Advantageously, the present invention is suitable for industrial-scale production of purified SLP derivatives and uses safe and environmentally friendly materials and methods.

[0094] In a preferred embodiment, the method of the present invention initially comprises producing a standardized SLP molecule "substrate" for producing a derived and / or purified SLP. In certain embodiments, this involves culturing a sophorolipid-producing yeast in a submerged fermentation reactor comprising a specialized oleochemical feedstock to produce a yeast culture product comprising a fermentation broth, yeast cells, and SLP having a mixture of two or more molecular structures.

[0095] The mixture of molecular structures may include, for example, lactone SLP, linear SLP, deacetylated SLP, monoacetylated SLP, diacetylated SLP, esterified SLP, SLP with different hydrophobic chain lengths, SLP attached with fatty acid-amino acid complexes, etc., including those SLPs described and / or not described in the present disclosure.

[0096] In certain embodiments, the distribution of the mixture of SLP molecules can be altered by adjusting fermentation parameters, such as feedstock, fermentation time, and dissolved oxygen content.

[0097] As used herein, "fermentation" refers to the growth or cultivation of cells under controlled conditions. Growth can be aerobic or anaerobic. Unless the context requires otherwise, the phrase is intended to encompass both the growth phase and the product biosynthesis phase of the process.

[0098] As used herein, "broth" or "culture broth" refers to a culture medium containing at least nutrients. If the culture broth is mentioned after the fermentation process, the culture broth may also contain microbial growth byproducts and / or microbial cells.

[0099] The microbial growth container used according to the present invention can be any industrial fermentation tank or culture reactor. As used herein, the term "reactor", "bioreactor", "fermentation reactor" or "fermentation vessel" includes a fermentation unit composed of one or more containers and / or towers or pipeline 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 towers, gas lift fermenters, static mixers, or other containers or other devices suitable for gas-liquid contact. In some embodiments, the bioreactor may include a first growth reactor and a second fermentation reactor. Therefore, when referring to adding a substrate to a bioreactor or a fermentation reactor, it should be understood to include adding to either or both of these reactors when appropriate.

[0100] In one embodiment, the fermentation reactor may have, or may be connected to, functional controls / sensors to measure important factors in the culture process, such as pH, oxygen, pressure, temperature, agitator shaft power, humidity, viscosity and / or microbial density and / or metabolite concentration.

[0101] In another embodiment, the container can also monitor the microbial growth within the container (e.g., cell number and growth period measurement). Alternatively, samples can be removed from the container for counting, purity measurement, SLP concentration and / or visible oil level monitoring. For example, in one embodiment, sampling can be performed once every 24 hours.

[0102] The microbial inoculum according to the method of the present invention preferably comprises cells and / or propagules of the desired microorganism which may be prepared using any known fermentation method. If desired, the inoculum may be premixed with water and / or liquid growth medium.

[0103] The microorganism used according to the present invention can be a natural or genetically modified microorganism. For example, a specific gene can be used to transform a microorganism to show a specific feature. Such microorganisms can also be mutants of desired strains. As used herein, "mutant" means a strain, genetic variant or subtype of a reference microorganism, wherein the mutant has one or more genetic variations (e.g., point mutations, missense mutations, nonsense mutations, deletions, duplications, frameshift mutations or repeated amplifications) compared to the reference microorganism. The procedures for making mutants are well known in the field of microbiology. For example, UV mutagenesis and nitrosoguanidine are widely used for this purpose.

[0104] 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, yeasts of the genus Starmosaccharomyces and / or yeasts of the genus Candida, such as Bombus spp. Starmosaccharomyces (Candida), Candida apicola, Candida batistae, Candida floricola, Candida riodocensis, Candida stellate and / or Candida kuoi. In a specific embodiment, the microorganism is Bombus spp. Starmosaccharomyces, such as strain ATCC 22214.

[0105] In certain embodiments, the culturing methods utilize submerged fermentation in a liquid growth medium comprising a specialized oleochemical feedstock.

[0106] In one embodiment, the liquid growth medium comprises one or more carbon sources. The carbon source can be a carbohydrate such as glucose, dextrose, sucrose, lactose, fructose, trehalose, mannose, mannitol and / or maltose; an organic acid such as acetic acid, fumaric acid, citric acid, propionic acid, malic acid, malonic acid and / or pyruvic acid; an alcohol such as ethanol, propanol, butanol, amyl alcohol, hexanol, isobutanol and / or glycerol; fats and oils such as canola oil, bauhinia 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.

[0107] In a preferred embodiment, the fermentation medium comprises dextrose. In another preferred embodiment, the oleochemical raw material is adjusted to include an oleic acid source. In certain embodiments, the oleic acid content is high, such as at least 75%, at least 80%, at least 85%, at least 90%, at least 95% or at least 99%. In some embodiments, the oleochemical raw material only comprises an oleic acid source.

[0108] 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, grape seed oil, sesame oil, poppy seed oil, pure oleic acid, redbud oil, oleic acid alkyl esters and / or oleic acid triglycerides. In a preferred embodiment, high oleic soybean oil, pure oleic acid and / or oleic acid alkyl esters are used.

[0109] Advantageously, in certain embodiments, the use of high oleic acid and / or oleic acid-only oleochemical feedstocks produces a yeast culture product containing a narrower diversity of SLP molecular structures than using feedstocks containing other fatty acid sources, wherein the predominant SLP molecules produced contain a C18 carbon chain and a single unsaturated bond at the ninth carbon. For example, in certain embodiments, greater than 50%, preferably greater than 70%, and more preferably greater than 85% of the SLP molecules contain a C18 carbon chain.

[0110] 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 a combination of two or more.

[0111] In one embodiment, one or more inorganic salts may also be included in the liquid growth medium. The inorganic salt may include, for example, potassium dihydrogen phosphate, monopotassium phosphate, dipotassium hydrogen phosphate, disodium hydrogen phosphate, potassium chloride, magnesium sulfate, magnesium chloride, iron sulfate, iron 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 a combination of two or more.

[0112] In one embodiment, the growth factor and micronutrients for microorganisms are included in the culture medium. Inorganic nutrients may also be included in the culture medium, and these inorganic nutrients include trace elements, such as iron, zinc, copper, manganese, molybdenum and / or cobalt. In addition, the source of vitamins, essential amino acids, proteins and trace elements may be included, such as corn flour, peptone, yeast extract, potato extract, beef extract, soybean extract, banana peel extract, etc., or they may be in a purified form. Amino acids may also be included, such as amino acids useful for the biosynthesis of proteins.

[0113] The culture method can also provide oxygenation for the growing culture. One embodiment uses slow movement of air to remove hypoxic air and introduce oxygenated air. The oxygenated air can be ambient air replenished daily by a mechanical device including an impeller for mechanically agitating the liquid and an air sparger for supplying gas bubbles to the liquid to dissolve oxygen into the liquid.

[0114] In certain embodiments, the dissolved oxygen (DO) content is controlled during fermentation to narrow the structural diversity of the produced SLP molecules in the yeast culture product. Preferably, the DO content is maintained at a high level so that, for example, oxygen transfer occurs at a rate 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.

[0115] In some embodiments, the culture method can also include adding additional acid and / or antimicrobial agents to the liquid medium before and / or during the culture process. Antimicrobial agents or antibiotics (e.g., streptomycin, oxytetracycline) are used to protect the culture from contamination. However, in some embodiments, the metabolites produced by the yeast culture provide sufficient antimicrobial effects to prevent the culture from being contaminated.

[0116] In one embodiment, the components of the liquid medium may be optionally sterilized prior to inoculating the reactor. In one embodiment, sterilization of the liquid growth medium may be achieved by placing the components of the liquid medium in water at a temperature of about 85° C. to 100° C. In one embodiment, sterilization may be achieved by dissolving the components in 1% to 3% hydrogen peroxide at a ratio of 1:3 (w / v).

[0117] In one embodiment, the equipment for cultivation is sterile. Cultivation equipment such as reactors / containers can be separated from, but connected to, a sterilization unit such as an autoclave. Cultivation equipment can also have a sterilization unit that is sterilized in situ before starting inoculation. Liners, openings, pipes and other equipment parts can be sprayed with, for example, isopropanol. Air can be sterilized by methods known in the art. For example, ambient air can pass through at least one filter before being introduced into the container. In other embodiments, the culture medium can be pasteurized, or optionally, the culture medium is not heated at all, wherein pH and / or low water activity can be used to control unwanted microbial growth.

[0118] The pH of the culture should be suitable for interested microorganisms. 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 adjusting agents such as carbonates and phosphates can be used to stabilize the pH near the preferred value. In certain embodiments, an alkaline solution such as 15% to 30% or 20% to 25% NaOH solution is used to adjust the pH of the culture to a favorable level. An alkaline solution can be included in the growth medium, and / or an alkaline solution can be fed into the fermentation reactor to regulate the pH during the incubation period as required.

[0119] In one embodiment, the culturing 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 culturing can be carried out continuously at a constant temperature. In another embodiment, the culturing may be subjected to temperature changes.

[0120] According to the method of the present invention, microorganisms can be cultivated in a fermentation system for a period of time sufficient to achieve a desired effect, such as producing a desired amount of cell biomass or a desired amount of SLP. The microbial growth byproducts produced by the microorganisms can be retained in the microorganisms and / or secreted into the growth medium. The biomass content can be, for example, 5 g / l to 180 g / l or higher, 10 g / l to 150 g / l or 20 g / l to 100 g / l.

[0121] In certain embodiments, yeast culture fermentation occurs for about 40 hours to 150 hours, or about 48 hours to 140 hours, or about 72 hours to 130 hours, or about 96 hours to 120 hours. In certain specific embodiments, the fermentation time is in the range of 48 hours to 72 hours, or 96 hours to 120 hours.

[0122] In some embodiments, once the dextrose and / or oleic acid concentrate in the medium is depleted (e.g., the content is 0% to 0.5%), the fermentation cycle is terminated. In some embodiments, the end of the fermentation cycle is determined as the time point at which the microorganism has begun to consume trace amounts of SLP.

[0123] In certain embodiments, the production of SLP molecule "substrate" also includes post-fermentation changes in the produced SLP molecules in the yeast culture product. In one embodiment, this crude SLP composition is hydrolyzed to produce linear SLP. In some embodiments, the linear SLP is deacetylated. In some embodiments, the linear SLP is fully acetylated.

[0124] In some embodiments, the method comprises subjecting the crude SLP to alkaline hydrolysis. For example, in one embodiment, the crude SLP may be mixed with an equimolar to 1.5 molar alkaline solution such as sodium hydroxide, potassium hydroxide, and / or ammonium hydroxide solution to adjust the pH to, for example, about 4 to 11, about 5 to 11, about 6 to 12, or preferably about 7 to 9. In certain embodiments, this is achieved by treating the crude SLP with a hydroxide salt solution at an elevated temperature, for example, 75°C to 100°C, 80°C to 95°C, or 85°C to 90°C, for 2 hours to 24 hours, 3 hours to 20 hours, or 4 hours to 16 hours.

[0125] According to the method of the present invention, the hydrolysis process breaks the lactone bond of the lactone SLP and converts it into a crude linear SLP. In certain embodiments, a portion of the crude linear SLP is acetylated, diacetylated or fully acetylated, wherein the portion comprises, for example, 1% to 100%, 5% to 75% or 10% to 50% of the total amount of SLP molecules. In another embodiment, the monoacetylated or diacetylated SLP molecules can be deacetylated via the same alkaline hydrolysis process.

[0126] In some embodiments, when bystander cations are present or may be present during the hydrolysis process, a cation exchange resin is used to purify the crude linear SLP. More specifically, in preferred embodiments, the crude linear sophorolipid is circulated through an ion exchange bed containing cation exchange sites using, for example, a peristaltic pump or other type of pump for a period of, for example, 15 minutes to 20 hours, 3 hours to 15 hours, 4 hours to 12 hours, or preferably 30 minutes to 3 hours.

[0127] The amount of cation exchange sites can be, for example, equimolar to 1.5 molar of the hydroxide salt used for the base hydrolysis.

[0128] Advantageously, ion exchange resins provide a novel method for purifying SLP molecules as well as a novel method for neutralizing the pH of reaction products without the need for standard quenching methods that can dilute and / or alter the chemical composition of the final product.

[0129] In preferred embodiments, the linear SLP with the bystander cations removed serves as a standardized substrate for one or more derivatization and / or purification reactions.

[0130] Two-step generation of cationic SLP derivatives via aldehyde handles

[0131] After removal of the spectator cation, a two-step synthetic scheme can be employed to generate a reactive aldehyde handle on the purified linear SLP - the first isolated intermediate of the process of the invention - followed by installation of a naturally derived cationic biodegradable functional group. Sophorolipids containing unsaturated bonds at specific positions allow for site-directed functionalization of the SLP molecule.

[0132] Step 1 - Ozonolysis

[0133] In certain embodiments, the purified linear SLP is moved to a new clean vessel containing multiple air ejectors with a large surface area for ozonolysis.During ozonolysis of linear SLP, the olefin portion of the SLP molecule is converted to an ozonide, a reactive 5-membered ring.

[0134] In a preferred embodiment, the purified linear SLP is ozonated with 2 to 3 vvm of 100% ozone gas for 2 to 20 hours, 3 to 16 hours, or 4 to 10 hours. The temperature is preferably at or about -78°C.

[0135] In one exemplary embodiment, the purified linear SLP is ozonated with 3 vvm of 100% ozone gas for 4 hours. In other exemplary embodiments, the purified linear SLP is ozonated with 2 vvm of 100% ozone gas for 16 hours.

[0136] After ozonolysis, in certain embodiments, the SLP-ozonide is degassed with 2 to 3 vvm of compressed air for 2 to 20 hours, 3 to 16 hours, or 4 to 10 hours.

[0137] In one exemplary embodiment, SLP-ozonide is degassed with 3 vvm of compressed air for 4 hours. In another exemplary embodiment, SLP-ozonide is degassed with 2 vvm for 16 hours.

[0138] In a preferred embodiment, the SLP containing ozonide is reduced to give the 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 used in an equimolar concentration to the SLP-ozonide. The linear SLP aldehyde is then preferably allowed to reach room temperature.

[0139] Step 2—Reductive Amination

[0140] In a preferred embodiment, step two of generating a cationic SLP derivative via an aldehyde handle involves reductive amination of a linear SLP aldehyde.

[0141] In certain embodiments, reductive amination involves the introduction of a primary amine into the aldehyde handle under reducing conditions. This produces a stable secondary amine that acts as a covalent bond between the SLP "scaffold" and the "payload" of the primary amine.

[0142] First, in some embodiments, the linear SLP aldehyde is extracted from the aqueous mixture with ethyl acetate and concentrated and dried at a temperature of about 35° C. to 45° C. under reduced pressure (e.g., about 200 mbar to 250 mbar or about 240 mbar). The dried crude linear SLP aldehyde can then be dissolved in a reaction medium comprising tetrahydrofuran (THF) and / or water. The percentage of water used as the reaction medium preferably does not exceed 50% water, and is typically between 0% and 25%.

[0143] 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 (eg, formic acid, trifluoroacetic acid) may also be used.

[0144] In certain embodiments, the primary amine is a cationic amino acid, such as arginine, lysine or histidine. In certain embodiments, the primary amine is a short peptide containing a repeating sequence of cationic amino acids. In certain embodiments, the primary amine is a short peptide containing a glycine residue as a spacer between the SLP scaffold and the primary amine load and / or between the cationic amino acid residues.

[0145] 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.

[0146] In a preferred exemplary embodiment, the reaction uses an amino acid ethyl ester of arginine (Arg) and sodium triacetoxyborohydride as a reducing agent.

[0147] In another exemplary embodiment, the reaction uses an amino acid ethyl ester of histidine (His) or lysine (Lys) and sodium triacetoxyborohydride as a reducing agent.

[0148] In other exemplary embodiments, the peptide ethyl ester is Arg-Arg-Arg-Arg, Gly-Gly-Arg-Arg, Gly-Arg-Gly-Arg, Gly-Arg-Arg-Arg or other combinations in which individual residues may be substituted with Arg, His, Lys or glycine (Gly). In certain embodiments, the addition of a glycine spacer enhances the water solubility and / or alcohol solubility of the SLP derivative. In certain embodiments, the addition of a glycine spacer enhances the antimicrobial activity of the SLP derivative by, for example, increasing the chain length of the fatty acid moiety. Advantageously, the chain length can be increased without changing the fermentation parameters during the initial production of the linear SLP substrate.

[0149] Additional or alternative chemical transformations for obtaining linear sophorolipids containing aldehyde functionalities and secondary amines.

[0150] In certain embodiments, an alternative two-step approach using ozonolysis is employed to produce linear SLP aldehydes containing secondary amines.

[0151] In certain embodiments, the hydrolyzed linear SLP substrate serves as the starting material. In some embodiments, a protecting group can be installed on each alcohol group of the SLP sophorose ring. Non-limiting examples of protecting groups include acetyl, trimethylsilyl ether, and tert-butyldiphenylsilyl ether, but many examples of alcohol protecting groups are well known to those skilled in the art.

[0152] In a preferred embodiment, the olefin group of the SLP is converted to an aldehyde moiety without the use of ozonolysis. Instead, the olefin is epoxidized to an oxirane ring using a peracid reagent (an example of the Prilezhaev reaction) or osmium tetroxide. Examples of peracid reagents used according to the methods of the present invention include, but are not limited to, meta-chloroperbenzoic acid, peracetic acid, and performic acid.

[0153] The resulting epoxide ring is then opened to the vicinal diol. In certain embodiments, this is performed under acid catalysis (aqueous) or base catalysis (aqueous) conditions.

[0154] Finally, the vicinal diol is oxidatively cleaved to produce the aldehyde group. The oxidative cleavage of the vicinal diol can be accomplished by an appropriate oxidizing agent such as sodium periodate.

[0155] After oxidative cleavage of the vicinal diol, the protecting group, 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.

[0156] Once the aldehyde-containing linear sophorolipids are obtained, they can be converted to the aforementioned derivatized species by the chemical transformations outlined earlier.

[0157] In certain embodiments, it is desirable to maintain the original alkyl chain length while performing the chemical transformation to obtain the aldehyde functionality. This can be achieved in several ways.

[0158] In one embodiment, a two-step synthetic approach using lactone SLP as starting material is employed. Initially, the lactone SLP is subjected to alkaline hydrolysis to simultaneously remove the acetyl group and convert the free carboxylic acid group into a methyl ester. A reducing agent such as DIBAL-H can be used to convert the methyl ester into an aldehyde functional group. After obtaining a linear sophorolipid containing an aldehyde, it can be converted into the aforementioned derived species by the chemical transformations outlined earlier.

[0159] In another embodiment, linear sophorolipids containing aldehydes can be produced by direct reduction of the lactone bonds present in the lactone SLP fermentation product in one step. Under specific conditions, for example, in the case of forming a composite reducing agent (acid salt complex) between diisobutylaluminum hydride and tert-butyl lithium, the lactone bond can be directly reduced to an aldehyde in one step. In addition to the acid salt complex, other examples of possible reducing agents include, but are not limited to, acid salt complexes of tri-tert-butoxyaluminum hydride lithium (TBLAH), diisobutyl-tert-butoxyaluminum hydride lithium (LDBBA) and diisobutylaluminum hydride and n-butyl lithium. After obtaining a linear SLP containing an aldehyde, it can be converted into the aforementioned derivative substance by the chemical transformation outlined earlier.

[0160] Obtaining derivatized SLPs containing short-chain or long-chain amide functional groups

[0161] In certain embodiments, a linear SLP substrate can be installed with an amide containing a cationic amino acid functional group to produce a long-chain amide derivative (eg, C18).

[0162] In some embodiments, a linear SLP substrate can be converted to a short chain amide (eg, C9) by first, truncating the fatty acid tail via oxidative cleavage, and second, installing an amide containing a cationic amino acid functionality onto the truncated acid.

[0163] The coupling agent used in the amide installation according to the present invention may include, for example, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI / HOBt), benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PYBOP), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethylammonium tetrafluoroborate (TBTU) and / or N,N'-dicyclohexylcarbodiimide / 1-hydroxybenzotriazole (DCC / HOBt). In certain embodiments, the preferred coupling agent is EDCI / HOBt.

[0164] In certain embodiments, a similar reaction scheme can be used to convert a linear SLP comprising an aldehyde handle as previously described into a long or short chain amide. In some embodiments, a truncated acid can serve as a substrate for the installation of an aldehyde handle as previously described.

[0165] Ion exchange / purification

[0166] In certain embodiments, the unique cationic properties of the SLP derivatives of the present invention allow cation exchange resins to be used for selective purification, such as selective retention of cationic species and / or selective removal of unreacted SLP and SLPs that do not contain desired carbon chain lengths or characteristics. Thus, in certain embodiments, the present invention provides novel methods for purifying SLP and SLP derivatives using cation exchange resins.

[0167] In certain embodiments, after reductive amination, the cationic SLP derivative can be extracted from the reductive amination reaction mixture via standard liquid-liquid extraction using an organic solvent, preferably ethyl acetate, washed with pH 9.0 sodium carbonate buffer, and concentrated under reduced pressure (e.g., about 200 mbar to 250 mbar or about 240 mbar). The mixture can then be resuspended in deionized water and purified using a cation exchange resin.

[0168] In certain embodiments, the extracted cationic SLP is 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 SLP, for a period of 2 hours to 20 hours, 3 hours to 15 hours, or 4 hours to 12 hours, using, for example, a peristaltic pump or other type of pump.

[0169] In a preferred embodiment, the SLP cationic derivatives are removed from the resin by applying an electrolyte solution containing a high concentration of monovalent metal cations, wherein the high concentration is 1.5 to 15 molar equivalents or 2 to 10 molar equivalents relative to the concentration of the SLP cationic derivatives. The high concentration of monovalent metal cations outcompetes the bound SLP cationic derivatives, which causes them to be exchanged on the resin and produces a highly purified SLP cationic derivative stream.

[0170] In some embodiments, after reductive amination, the cationic SLP derivative can be purified by stirring it with a saturated ammonium chloride solution to produce a stirred mixture; extracting the cationic SLP derivative by applying CH2Cl2 solvent (3×) to the stirred mixture to produce an extraction mixture; removing traces of water from the extraction mixture by applying MgSO4 or Na2SO4; drying the extraction mixture under high pressure (e.g., 350 to 450 mbar or 400 mbar) and at 35° C. to 45° C. to remove the CH2Cl2 solvent; and applying 21% NaOEt / EtOH solution, NaHCO3 or KHCO3 base / ethanol to remove the acetyl R group from the cationic SLP derivative. The deacetylated linear cationic SLP derivative can then be converted to an HCl salt by reacting it with a 1.25 M HCl / EtOH solution.

Claims

1. A conditioning composition comprising a cationic sophorolipid (SLP) molecule which has been derivatized to have one of the following formulae: A B C D wherein R = arginine, lysine or histidine or a peptide comprising repeating sequences thereof, and R1 = H, acetyl, butyl or isobutyl.

2. The composition of claim 1, further comprising a non-derivatized SLP molecule.

3. The composition of claim 2, wherein the ratio of the cationically derivatized SLP to the non-derivatized SLP is from 1:10 to 1:1000. The composition according to claim 1 , further comprising mannose erythritol lipid MEL.

5. The composition of claim 4, wherein the ratio of the cation-derivatized SLP to the MEL is from 1:10 to 1:1000.

6. The composition of claim 4, wherein the ratio of the cation-derivatized SLP to the MEL is from 1000:1 to 10:

1.

7. The composition according to claim 1, further comprising one or more other components selected from the group consisting of: carriers, organic and / or inorganic solvents, organic and / or inorganic acids, essential oils, plant extracts, crosslinking agents, 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 blockers, humectants, film formers, minerals, vitamins, proteins, Viscosity regulators and / or rheology modifiers, insect repellents, skin cooling compounds, skin protectants, lubricants, pearls, chromalite, mica, antiallergic agents, antimicrobials, antifungals, antivirals, antibacterials, fungicides, pharmaceutical agents, light stabilizers, surface smoothing agents, optical diffusers, exfoliation accelerators, antistatic agents, anti-wrinkle agents, wetting agents, dye transfer aids, color protection agents, deodorants, odor traps, detergents, drying agents, water repellents, anti-pilling agents, acidulants, starch agents, optical brighteners, antioxidants, shrinkage control agents, starch and mixtures thereof.

8. The composition of claim 1, formulated as a liquid; colloidal dispersion; micro- or nanoemulsion; gel; serum; granulated powder, spray-dried powder or dry-blended powder; solid bar; concentrate; encapsulated soluble pods; suspension; hydrogel; multiphase solution; vesicular dispersion; foam; mousse; spray; aerosol; liquid cake; ointment; essence; paste; tablet; water-soluble sheet or pouch; and / or capable of being impregnated into a dry or pre-moistened substrate such as a sheet, ball, cloth, sponge or wipe.

9. A method for conditioning hair, fibers or textiles, said method comprising contacting said hair, said fibers or said textiles with a conditioning composition comprising a cationically derivatized sophorolipid (SLP) molecule, wherein said derivatized SLP molecule has one of the following formulae: A B C D wherein R = arginine, lysine, glycine or histidine or a peptide comprising repeating sequences thereof, and R1 = H, acetyl, butyl or isobutyl.

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

11. The method of claim 10, wherein the ratio of the derivatized cationic SLP to the non-derivatized SLP is 1:10 to 1:1000.

12. The method of claim 9, further comprising contacting a mannoerythritol lipid MEL with the hair, the fiber, or the textile.

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

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

1.

15. The method according to claim 9, wherein the conditioning composition further comprises one or more other components selected from the group consisting of: carriers, organic and / or inorganic solvents, organic and / or inorganic acids, essential oils, plant extracts, crosslinking agents, 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 blockers, humectants, film formers, minerals, vitamins, Proteins, viscosity regulators and / or rheology modifiers, insect repellents, skin cooling compounds, skin protectants, lubricants, pearls, chromalite, mica, antiallergic agents, antimicrobials, antifungals, antivirals, antibacterials, fungicides, pharmaceutical agents, light stabilizers, surface smoothing agents, optical diffusers, exfoliation accelerators, antistatic agents, anti-wrinkle agents, wetting agents, dye transfer aids, color protection agents, deodorants, odor traps, detergents, drying agents, water repellents, anti-pilling agents, acidulants, starch agents, optical brighteners, antioxidants, shrinkage control agents, starch and mixtures thereof.

16. The method of claim 9, wherein after said effective amount of contact time said conditioning composition is rinsed from said hair, said fibers or said textiles with water or a solvent to effect conditioning.

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

18. The method of claim 9, wherein the method imparts one or more of the following benefits to the hair, the fiber, or the textile: reduced static and / or frizz; increased strength; reduced breakage; reduced tangles and mattness; improved shine and softness; increased oil and / or water retention; reduced wrinkles; and / or imparted fragrance.

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

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

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

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