Compositions of n-acylated proline or derivatives thereof and their use

Abstract

Compositions of N-acylated proline or derivatives thereof and their use This invention deals with compositions of N-acylated proline or derivatives thereof and their uses, for example in laundry or dishwashing.

Description

2410741Compositions of N-acylated proline or derivatives thereof and their useThis invention deals with specific compositions of N-acylated proline or derivatives thereof (in this present invention abbreviated as "inventive composition” or "compounds of the invention” whenever the inventive compositions are meant) comprising at least one N-acylated proline or derivative thereof and at least one N-acylated glutamate or derivative thereof, their uses and compositions including the inventive compositions, particularly as laundry detergent compositions.Anionic surfactants, particularly the sulphonates such as linear alkylbenzene sulphonate (LAS) and the sulphates such as alkyl ether sulfates (AES, in particular SLS (sodium laureth sulfate)) and primary alkyl sulphate (PAS), are the key ingredients of modern laundry detergents, providing excellent detergency performance on a wide range of soils and stains.However, detergent formulators are continuously faced with the task to improve the environmental "footprint” of any product, be it in terms of its origin like being from natural or renewable resources, or compared to previous products, its production in terms of production efficiency and thus reduced usage of energy, its efficiency in usage such as reduced amounts for the same performance or higher performance at the same amount levels used, its persistence in the natural environment after its usage, especially its biodegradation, since recycling is technically very challenging and therewith economically not attractive.Hence, due to the climate change, one of the most important targets of the detergent and cleaner (D&C) industry today is to significantly lower the CO2 emission per wash. Surfactants, such as LAS are based on fossil carbon sources and therefore their production is incompatible with the environmental-friendly aims of the D&C industry. AES might comprise 1 ,4-dioxane as by-product and therefore alternatives free of 1 ,4-dioxane are desired.Additionally, the industry is looking for surfactants that provide a high degree of biodegradability after their use and release into the environment.To overcome these problems, alternative surfactants that provide significant wash performance and which are (or can potentially be) based on non-fossil carbon sources and provide a high degree of biodegradability are of interest for the D&C industry.One such alternative group of surfactants are amino acid-based surfactants, such as N-acylated lysine and proline.In the following, a summary of the current knowledge and most relevant publications in the field of the present invention, the use of N-acylated proline and similar compounds is given.WC2018206878 A1 and WC2009118493 A2 describe specific synthesis methods for N-acylated proline. However, these patents documents provide no information about functional data of the synthesized compounds, let alone any data with respect to cleaning and wash performance. Therefore, these documents provide no hint to combine N- acylated proline with N-acylated glutamate to increase its surfactant and wash performance.2410742CN104219964 B and US10, 711 ,230 B2 describe the use of N-acylated proline in food compositions. In CN104219964 B the N-acylated proline is described as a food fragrance compound, whereas in US10, 711 ,230 B2 it is mentioned that N-acylated proline can be used as a food flavoring compound. As before, none of these documents provides no hints to combine N-acylated proline with N-acylated glutamate to increase its surfactant and wash performance.EP3621959 A1 describes a composition comprising acylated amino acid based on proline, acylated dipeptide (based on the proline), fatty acid and optionally dipeptide based on proline. In addition, a process for the manufacturing and cosmetic compositions are revealed. Also here, the document provides no hints to combine N- acylated proline with N-acylated glutamate to increase its surfactant and wash performance.Sreenu et al. (Sreenu, M. et al. (2015), j. Oleo Sci. 64, (11), pages 1175-1184) describe the surface-active properties of N-acyl prolines. When the N-acyl prolines are compared to sodium laureth sulfate (SLS) they show inferior performance in wetting time, surface tension and foam height. These disadvantages can be overcome by combining the N-acylated proline with N-acylated glutamate as experimentally demonstrated by the present inventors.The cleaning and personal care industry is well-aware of the potential of acylated amino acids as surfactants. One example of such amino acid-based surfactants is N-acylated lysine as described by Shi et al. (Shi, T.T. RSC Adv. 2019 Mar 1 ; 9(13): 7587-7593.). However, a combination of N-cocoyllysine sodium salts shows significantly weaker overall wash performance than combinations of N-acylated prolines.In contrast to above-described documents, the present invention is not directed to a single N-acylated proline or N- acylated lysine but to a combination of N-acylated proline and N-acylated glutamate.Thus, the present inventors surprisingly found that combining at least one N-acylated proline and at least one N- acylated glutamate, preferably in a ratio wherein the N-acylated proline possesses the weight majority, will provide synergistic effects in wash properties over the ones observed for comparable single compounds. This results in a composition of surfactants that has significant wash performance and can potentially be based on non-fossil carbon sources and can potentially provide a significant degree of biodegradability.Therefore, the object of the present invention is to provide novel compositions comprising(1) at least one compound according to Formula (1)whereinR1 is an aliphatic, saturated or unsaturated, linear or branched moiety comprising 7 to 17 carbon atoms, and241074 the dotted lines indicate ording to Formula (2)whereinM+is selected from the group consisting of H+, Na+, K+, NH4+, protonated amine and protonated amino alcohol, or ii) bonds to the remaining parts of the compound according to Formula (1), wherein at least one remaining part comprises at least one five-membered ring and a directly bound moiety according to Formula (3); and(2) at least one compound according to Formula (3)wherein n is an integer between 1 and 5;R2 is an aliphatic, saturated or unsaturated, linear or branched moiety comprising 7 to 17 carbon atoms; andM+is as defined above.In another aspect, the invention is directed to a cleaning method and uses of the inventive composition in cleaning formulations and compositions.Thus, subjects of the present invention are the following Embodiments 1 to 15 as defined and further explained with further embodiments hereinafter and further exemplified in the experimental section.Embodiment 1A composition comprising(1) at least one compound according to Formula (1)241074whereinR1 is an aliphatic, saturated or unsaturated, linear or branched moiety comprising 7 to 17 carbon atoms, and the dotted lines indicateI) a moiety according to Formula (2)whereinM+is selected from the group consisting of H+, Na+, K+, NH4+, protonated amine and protonated amino alcohol, or ii) bonds to the remaining parts of the compound according to Formula (1), wherein at least one remaining part comprises at least one five-membered ring and a directly bound moiety according to Formula (3); and(2) at least one compound according to Formula (3)wherein n is an integer between 1 and 5;R2 is an aliphatic, saturated or unsaturated, linear or branched moiety comprising 7 to 17 carbon atoms; andM+is as defined above.The inventive composition is directed to I) N-acylated proline or derivatives thereof and ii) N-acylated glutamate or derivatives thereof. Basically, these compounds comprise at least one alkyl part that is attached to the nitrogen atom of the amino acids.Proline, the starting compound for N-acylated proline, can be derived by chemical synthesis or by fermentation. If derived by chemical synthesis, the synthesis of proline is based on using glutamic acid as a raw material,2410745 subsequent esterification with absolute ethanol under the catalysis of sulfuric acid, and then triethanolamine is added to free the aminosulfate to obtain glutamic acid-6-ethy I ester. The glutamic acid-5-ethyl ester is then reduced with a metal reducing agent potassium borohydride to obtain crude proline, which is finally separated and purified to obtain crude L-proline.In preferred embodiments, the proline of the N-acylated proline is obtained by fermentation. Such processes are well-known in the art, for example as described in US4444885 A. More preferably a microorganism is used for fermentation, such as a bacterium, preferably selected from the group consisting of Corynebacterium, Arthrobacter, Brevibacterium, and Microbacterium or a yeast, such as Saccharomyces. The fermentatively derived proline acids possess at least 10%, at least 20%, at least 40%, at least 70%, at least 95% or even 100% non-fossil derived carbon atoms.Also, glutamate or glutamic acid, starter compounds for N-acylated glutamate, can be derived by chemical synthesis or by fermentation. The chemical synthesis may involve hydrolysis of vegetable proteins with hydrochloric acid to disrupt peptide bonds or direct chemical synthesis with acrylonitrile.However, preferably the glutamate or glutamic acid is derived from fermentation. The producing organism may be chosen among the genus of bacteria including Corynebacterium glutamicum, Brevibacterium lactofermentum, and Brevibacterium flavum. The fermentatively derived glutamate or glutamic acid possess at least 10%, at least 20%, at least 40%, at least 70%, at least 95% or even 100% non-fossil derived carbon atoms.The above-described amino acids proline and glutamate can be reacted with fatty acids to arrive at the N-acylated proline and N-acylated glutamate of the inventive composition. The fatty acids are aliphatic, saturated or unsaturated, linear or branched compounds comprising 8 to 18 carbon atoms. The fatty acids are preferably derived from animal oils, such as fish oil, or plant oils, such as coconut oil, palm kernel oil, palm oil, seed oils, in particular peanut, olive oil, corn oil, soya bean oil, sunflower oil, sunflower seed oil, linseed oil and rapeseed oil. Thus, the fatty acids possess at least 10%, at least 20%, at least 40%, at least 70%, at least 95% or even 100% non-fossil derived carbon atoms.Thus, in preferred embodiments the amount of non-fossil carbon atoms in one or all of the N-acylated amino acids of the inventive composition is at least 10%, at least 20%, at least 40%, at least 70%, at least 95% or they solely comprise non-fossil derived carbon atoms compared to the total amount of carbon atoms in the N-acylated amino acids.The integer “n” is preferably 1 , 2, 3, 4 or 5.The term "salts of the inventive compounds”, as used herein, refers to compound complexes having an anionic part and a cationic part. The amino acid, proline or glutamate, represents the anionic part (usually in form of a deprotonated carboxyl group). It is noted that the stoichiometric ratios between the anionic and cationic part may be 1 : 1 , but also ratios, such as 1 :2, 1 :3, 2:3, 2:1 , 3:1 and 3:2 are possible. In further preferred embodiments, at2410746 least 50%, at least 60%, at least 70%, at least 80%, at least 90%, at least 95%, at least 98%, at least 99% or 100% of the amino acids of the inventive composition are represent as a salt.Each of the N-acylated prolines and the N-acylated glutamates of the inventive composition comprises ester bonds. It is expected that these ester bonds can be hydrolyzed by enzymes of microorganisms, forming non-toxic degradation products, including proline or glutamate and fatty acids. Therefore, significant biodegradability rates can be expected for the composition of the invention and in preferred embodiments the inventive composition demonstrates at least 20%, preferably at least 40%, more preferably at least 60% or even more preferably at least 80% biodegradability according to standard OECD 301 F within 56 days, preferably within 28 days. For the purposes of this invention, aerobic biodegradation in wastewater according to OECD 301 F is expressed as a percentage of the theoretical oxygen demand (ThOD, which is measured by the elemental analysis of the compound of interest), which is needed to completely biodegrade the polymer sample. Thus, the amount of oxygen taken up by the microbial population during biodegradation of the test substance (corrected for uptake by blank inoculum, run in parallel) is expressed as a percentage of ThOD. The obtained values are preferably measured in triplicate using the OECD 301 F manometric respirometry method. The consumption of oxygen is determined by measuring the change in pressure in the apparatus using an OxiTop® C (Xylem 35 Analytics Germany Sales GmbH & Co KG). Details for the tests performed are given in the experimental section below.The term "at least one”, as used herein, includes but is not limited to 1 , 2, 3, 4, 5, 6, 7, 8, 9 or more.The terms "essentially consisting of” or "consisting essentially of”, as used interchangeably herein, with respect to the inventive N-acylated amino acid composition mean that the composition may comprise impurities or other types of (modified) amino acids or derivatives thereof in an amount up to not more than 10% w / w, not more than 7% w / w, not more than 5% w / w, not more than 3% w / w, not more than 2% w / w, not more than 1 % w / w, not more than 0.5% w / w or not more than 0.1 % w / w.The term "at least one remaining part comprises at least one five-membered ring and a directly bound moiety according to Formula (3)”, as used herein, means that the overall compound comprises one, two or three additional five-membered rings, preferably one additional five-membered ring that possesses a directly bound carboxyl group, preferably a moiety according to Formula (2). In more preferred embodiments, the compound falling under alternative ii) is the compound according to Formula (5)."Pronated amine”, as used herein, means any protonated amine, namely ammonium, primary, secondary and tertiary amines. Amines that can be protonated and can form a salt with the above-described compounds include methylamine, ethylmethylamine and trimethylamine.The term "amino alcohol", as used herein, refers to a chemical entity containing both an amino group and a hydroxyl moiety. The skilled person knows that the amino groups of these compounds can be protonated.Embodiment 22410747The composition according to Embodiment 1 , wherein the compound according to Formula (1) has a structure according to one formula selected from the group consisting of Formula (4) and (5):whereinM+and R1 are as defined above.Embodiment 3The composition according to Embodiment 1 or 2 comprising a compound according to Formula (4).In preferred embodiments, the composition of the invention comprises, essentially consists of or consists of I) one compound according to Formula (4), and ii) one compound according to Formula (3).Embodiment 4The composition according to any one of Embodiments 1 to 3, wherein n is 1 or 2, preferably 2.Embodiment 5The composition according to any one of Embodiments 1 to 4, wherein R1 and R2 are independently of each other an aliphatic, saturated or unsaturated, preferably saturated, linear or branched, preferably linear moiety comprising 9 to 16, 10 to 15 or 11 to 13 carbon atoms.Embodiment 6The composition according to any one of Embodiments 1 to 5, wherein M+is selected from the group consisting of Na+, K+and NH4+.Embodiment 7The composition according to any one of Embodiments 1 to 6, wherein(I) the content of the at least one compound according to Formula (1) is at least 75 wt% of the sum of the weights of the compounds according to Formula (1) and (3), and2410748(ii) the content of the at least one compound according to Formula (3) is at least 1 wt% of the sum of the weights of the compounds according to Formula (1) and (3).Embodiment sThe composition according to any one of Embodiments 1 to 7, wherein(i) the content of the at least one compound according to Formula (1) ranges from 85 to 99 wt% of the sum of the weights of the compounds according to Formula (1) and (3), and(ii) the content of the at least one compound according to Formula (3) ranges from 1 to 15 wt% of the sum of the weights of the compounds according to Formula (1) and (3).In further preferred embodiments, the content of the at least one compound according to Formula (1) ranges from 88 to 98 wt%, 92 to 97 wt% and 94 to 96 wt% of the sum of the weights of the compounds according to Formula (1) and (3).In further preferred embodiments, the content of the at least one compound according to Formula (3) ranges from 2 to 12 wt%, 3 to 8 wt% and 4 to 6 wt% of the sum of the weights of the compounds according to Formula (1) and (3).Embodiment 9The composition according to any one of Embodiments 1 to 8, wherein the composition is a liquid composition."Liquid”, as used herein, means that a continuous phase or predominant part of the composition is liquid and that the composition is flowable at 20°C (i.e., suspended solids may be included). The term "liquid” also includes gels. "Gel”, as used herein, means a shear thinning, lamellar gel, with a pouring viscosity in the range of from 100 to 5000 mPa*s (milli Pascal seconds), more preferably less than 3000 mPa*s, most preferably less than 1500 mPa*s. The gel can be a thick liquid. A different type of liquid gel is shear-thinning, i.e. it is thick at low shear condition (e.g., at rest) and thin at high flow rate condition.Embodiment 10The composition according to Embodiment 9, wherein the liquid composition i) comprises Ca2+ions; and ii) comprises, by weight of the composition, from 5% to 95% of water.In preferred embodiments, the inventive composition may comprise calcium (Ca2+) present in an amount ranging from 0.0001 % to 3%, preferably from 0.001 % to 1 % by weight of the composition.2410749In preferred embodiments, the lower limit of the calcium concentration is 0.0005%, 0.001 % or 0.005% by weight of the inventive composition. In other preferred embodiments, the upper limit of the calcium concentration is 2.5%, 2% or 1.5% by weight of the inventive composition.Further, in preferred embodiments the composition of the invention comprises magnesium (Mg2+) in an amount ranging from 0.0001% to 3%, more preferably from 0.001 % to 1% by weight of the composition.In further embodiments, the liquid composition of the invention comprises, by weight of the composition, from 20% to 90%, 40% to 85%, 60% to 80% or 70% to 75% of water.Embodiment 11The composition according to any one of Embodiments 1 to 10, wherein the composition is a cleaning composition, fabric and home care product, industrial and institutional cleaning product, wetting agent, cosmetic formulation, crude oil emulsion breaker, oil recovery formulation, formulation for corn oil separation, formulation for fermentation process, flotation agent of mineral ores, pigment dispersion for ink jet inks, formulation for electro plating, cementitious composition, in gypsum compositions, dispersant or wetting agent or emulsifier, comprising, consisting of or essentially consisting of the composition according to any of Embodiments 1 to 10, preferably a cleaning composition and / or fabric and home care product and / or industrial and institutional cleaning product, comprising the composition according to any of Embodiments 1 to 10.A subject matter of the present invention is the use or the specific formulation of the above-mentioned inventive composition comprising the N-acylated amino acids in / for fabric and home care products, in industrial and institutional cleaning products, in cosmetic formulations, as wetting agents, as crude oil emulsion breaker, in pigment dispersions for ink jet inks, in formulations for electro plating, in cementitious compositions, in gypsum compositions, and / or as dispersant or wetting agent or emulsifier, preferably in cleaning compositions and / or in fabric and home care products, in particular cleaning compositions for improved clay removal or oily and fatty stain removal, wherein the cleaning composition is preferably a laundry detergent formulation and / or a manual dish wash detergent formulation, more preferably a liquid laundry detergent formulation and / or a liquid manual dish wash detergent formulation.The inventive composition can be added to cosmetic formulations, as crude oil emulsion breaker, in pigment dispersions for ink jet inks, formulations for electro plating, in cementitious compositions. However, the inventive composition can also be added to (used in) washing or cleaning compositions.Another subject-matter of the present invention is, therefore, a cleaning composition, fabric and home care product, industrial and institutional cleaning product, cosmetic formulation, wetting agent, crude oil emulsion breaker, pigment dispersion for ink jet inks, formulation for electro plating, cementitious composition and / or dispersant or wetting agent or emulsifier, comprising the combination of N-acylated amino acids, as defined above.Preferably, it is a cleaning composition and / or fabric and home care product, comprising the combination of N- acylated amino acids, as defined above, preferably for improved clay removal or oily and fatty stain removal, preferably a laundry detergent formulation and / or a manual dish wash detergent formulation, more preferably a liquid laundry detergent formulation and / or a liquid manual dish wash detergent formulation.In another preferred embodiment of the present invention, the cleaning composition may be used for soil removal of particulate stains and / or oily and fatty stains, and additionally for whiteness maintenance, preferably in laundry care.In another embodiment, the cleaning composition of the present invention is a hard surface cleaning composition that may be used for cleaning various surfaces such as hard wood, tile, ceramic, plastic, leather, metal, glass.In another embodiment, the cleaning composition of the present invention is a liquid or solid automatic dish wash detergent composition, preferably a solid automatic dish wash detergent composition, that may be used for cleaning dish ware, e.g., dish ware such as glasses, wherein the inventive composition is improving the removal of stubborn soils.In another embodiment, the cleaning composition is designed to be used in personal care and pet care compositions such as shampoo compositions, body wash formulations, liquid or solid soaps.In this invention, a preferred area of application for the use of the combination of N-acylated amino acids is the field of fabric and home care products and cleaning compositions, preferably cleaning compositions for industrial and institutional use and the use by consumers in their household.Embodiment 12The composition according to Embodiment 11 , wherein the composition is a cleaning composition further comprising i) at least one cleaning polymer or soil release polymer, and / or ii) at least one further surfactant selected from the group consisting of anionic surfactants and / or non-ionic surfactants and / or amphoteric surfactants and / or zwitterionic surfactants and / or cationic surfactants, and / or iii) an antimicrobial agent selected from the group consisting of 2-phenoxyethanol and 4,4'-dichoro 2- hydroxydiphenylether; preferably comprising 2-phenoxyethanol in an amount ranging from 2 ppm to 5% by weight of the composition; more preferably comprising 0.1 to 2% of phenoxyethanol or preferably comprising 4,4'-dichoro 2-hydroxydiphenylether in a concentration from 0.001 to 3%, more preferably 0.002 to 1 %, even more preferably 0.01 to 0.6%, each by weight of the composition, and / or iv) at least one enzyme selected from the list consisting of lipases, hydrolases, amylases, DNases, proteases, cellulases, hemicellulases, phospholipases, esterases, mannanases, xylanases, dispersins, oxidoreductases, cutinases, pectate lyases, pectinases, lactases and peroxidases, and combinations of at least two of the foregoing11 types, preferably selected from one or more lipases, hydrolases, amylases, proteases, cellulases, and combinations of at least two of the foregoing types, more preferably at least one enzyme being selected from proteases, and / or v) at least one compound selected from the group consisting of builders, cobuilders, structurants or thickeners, clay soil removal / anti-redeposition agents, polymeric soil release agents, dispersants such as polymeric dispersing agents, polymeric grease cleaning agents, solubilizing agents, chelating agents, enzymes, enzyme stabilizing systems, bleaching compounds, bleaching agents, bleach activators, bleach catalysts, brighteners, malodor control agents, pigments, dyes, opacifiers, hueing agents, dye transfer inhibiting agents, chelating agents, suds boosters, suds suppressors (antifoams), color speckles, silver care, anti-tarnish and / or anti-corrosion agents, alkalinity sources, pH adjusters, pH-buffer agents, hydrotropes, scrubbing particles, antibacterial agents, anti-oxidants, softeners, carriers, processing aids, pro-perfumes, dye fixation agent and perfumes, vi) cosolvent selected from groups of aliphatic alcohols, diols (preferably propylene glycole), or triols comprising 2 to 5 carbon atoms or selected from group of ethylene glycole or diethylene glycol mono alkyl ether comprising 2 to 5 carbon atoms in alkyl moiety or selected from group of propylene glycole or dipropylene glycol mono alkyl ether comprising 2 to 5 carbon atoms in alkyl moiety, and / or vii) water.In alternatively preferred embodiments, the cleaning composition of the invention does not comprise further (anionic) surfactants in addition to the N-acylated amino acids.Embodiment 13Use of the composition according to any one of Embodiments 1 to 10 in cleaning compositions, in fabric and home care products, in institutional and industrial cleaning products, in cosmetic formulations, as crude oil emulsion breaker, as surfactant in enhanced oil recovery, as surfactant in corn oil separation, as surfactant in fermentation processes, as surfactant in flotation of mineral ores, in pigment dispersions for inkjet inks, in formulations for electro plating, in formulations for emulsion polymerization, in formulations for dispersions, in cementitious compositions, in gypsum compositions, as dispersant or wetting agent or emulsifier.Embodiment 14The use according to Embodiment 13 in cleaning compositions and / or in fabric and home care products, preferably in cleaning compositions for i) improved removal of oily / fatty stains, and / or ii) improved removal of sebum, and / or iii) clay removal, and / or iv) soil removal of particulate stains, and / or24107412 v) dispersion and / or emulsification of soils, and / or vi) modification of treated surface to improve removal upon later re-soiling, and / or vii) whiteness improvement and / or preferably in cleaning compositions for removal of oily / fatty stains, each of the before mentioned options I) to vii) preferably for use in a laundry detergent formulation and / or a manual dish wash detergent formulation and / or in a formulation suitable for (pre)-treatment of textiles and / or soap bars, more preferably in a liquid laundry detergent formulation and / or a liquid manual dish wash detergent formulation.Embodiment 15A cleaning method comprising contacting a cleaning composition of the invention with an object that requires cleaning, preferably a laundry or a hard surface household item.The term "cleaning”, as used herein, refers to performing or aiding in any soil removal, bleaching, microbial population reduction, or combination thereof. This includes to rinse a fabric with water or to wash the fabric with the inventive liquid cleaning composition by means of a washing machine, automatic dish washer or by hand. It is preferred that the cleaning is carried out at a temperature of 60 °C or less, more preferably at a temperature of 40 °C or less, most preferably at a temperature of 30 °C or less. In other preferred embodiments, the cleaning method is performed under water conserving conditions. This means that not more than 60%, not more than 70%, not more than 80%, not more than 90% or not more than 95% of the water generally recommended for a given cleaning procedure is used for the cleaning method of the present invention.The following examples shall further illustrate the present invention without restricting the scope of the invention.The specific embodiments as described throughout this disclosure are encompassed by the present invention as part of this invention; the various further options being disclosed in this present specification as "optional”, "preferred”, "more preferred”, "even more preferred” or "most preferred” (or "preferably” etc.) options of a specific embodiment may be individually and independently (unless such independent selection is not possible by virtue of the nature of that feature or if such independent selection is explicitly excluded) selected and then combined within any of the other embodiments (where other such options and preferences can be also selected individually and independently unless such independent selection is not possible by virtue of the nature of that feature or if such independent selection is explicitly excluded), with each and any and all such possible combinations being included as part of this invention as individual embodiments.As used herein, the articles "a” and "an” when used in a claim or an embodiment, are understood to mean one or more of what is claimed or described. As used herein, the terms “include(s)” and "including” are meant to be nonlimiting, and thus encompass more than the specific item mentioned after those words.24107413The compositions of the present disclosure can "comprise” (i.e. , contain other ingredients), "consist essentially of' (comprise mainly or almost only the mentioned ingredients and other ingredients in only very minor amounts, mainly only as impurities), or "consist of” (i.e., contain only the mentioned ingredients and in addition may contain only impurities not avoidable in a technical environment, preferably only the ingredients) the components of the present disclosure.Similarly, the terms "substantially free of ...” or "substantially free from ...” or “(containing / comprising) essentially no ...” may be used herein; this means that the indicated material is at the very minimum not deliberately added to the composition to form part of it, or, preferably, is not present at analytically detectable levels. It is meant to include compositions whereby the indicated material is present only as an impurity in one of the other materials deliberately included. The indicated material may be present, if at all, at a level of less than 1 %, or even less than 0.1 %, or even more less than 0.01 %, or even 0%, by weight of the composition.The term "about”, as used herein, encompasses the exact number "X” mentioned as e.g., "about X%” etc., and small variations of X, including from minus 5 to plus 5 % deviation from X (with X for this calculation set to 100%), preferably from minus 2 to plus 2 %, more preferably from minus 1 to plus 1 %, even more preferably from minus 0,5 to plus 0,5 % and smaller variations. Of course, if the value X given itself is already "100%” (such as for purity etc.) then the term "about” clearly can and thus does only mean deviations thereof which are smaller than "100”.Unless otherwise noted, all component or composition levels are in reference to the active portion of that component or composition, and are exclusive of impurities, for example, residual solvents or by-products, which may be present in commercially available sources of such components or compositions.All temperatures herein are in degrees Celsius (°C) unless otherwise indicated. Unless otherwise specified, all measurements herein are conducted at 20°C and under atmospheric pressure. In all embodiments of the present disclosure, all percentages are by weight of the total composition, unless specifically stated otherwise. All ratios are weight ratios, unless specifically stated otherwise.Description of cleaning compositions, formulations and their ingredientsThe publication IPCCM000274907D published on www.IP.com is regarded as Reference RF1 , which is incorporated herein by reference in its entirety. The publication Prior Art Disclosure; Issue 684; paragraphs

[3000] to

[3061] ; ISSN: 2198-4786; published: February 12, 2024 will be regarded as Reference RF2, which is incorporated herein by reference in its entirety.The phrase "cleaning composition", as used herein, includes compositions and formulations designed for cleaning soiled material. Such compositions and formulations include those designed for cleaning soiled material or surfaces of any kind, more preferably compositions for Fabric and Home Care. "Cleaning compositions” are defined in more detail in paragraphs

[0001] ,

[0002] ,

[0004] and

[0007] of Reference RF1.24107414"Compositions for Fabric and Home Care” include cleaning compositions and formulations including but not limited to laundry cleaning compositions and detergents and hard surface cleaning compositions including dish washing compositions, more preferably liquid laundry formulations, solid laundry compositions, liquid manual dish wash formulations, automatic dish wash (ADW) gels and automatic dish wash (ADW) solid compositions. "Compositions for Fabric and Home Care” are defined in more detail in paragraph

[0003] of Reference RF1.The cleaning compositions of the invention including the inventive surfactant(s) may - and preferably do - contain adjunct cleaning additives (also abbreviated herein as "adjuncts”), such adjuncts being preferably in addition to a surfactant system as defined before.Suitable adjunct cleaning additives include polymers, further surfactants or surfactant systems, builders, cobuilders, enzymes, enzyme stabilizing systems, structurants or thickeners, clay soil removal / anti-redeposition agents, solubilizing agents, chelating agents, bleaching compounds, bleaching agents, bleach activators, bleach catalysts, brighteners, malodor control agents, pigments, dyes, opacifiers, hueing agents, dye transfer inhibiting agents, chelating agents, suds boosters, suds suppressors (antifoams), color speckles, silver care, anti-tarnish and / or anti-corrosion agents, alkalinity sources, pH adjusters, pH-buffer agents, hydrotropes, scrubbing particles, antibacterial agents, anti-oxidants, softeners, carriers, processing aids, pro-perfumes, dye fixation agent and perfumes.In preferred embodiments, the cleaning compositions comprise the inventive surfactant(s) and a polymer, preferably cleaning polymers and / or soil release polymers. "Cleaning polymers and soil release polymers” are defined in more detail in paragraphs

[0032] to

[0034] of Reference RF1. These polymers include polycarboxylates, alkoxylated polyalkylenamines, alkoxylated polyalkylenimines, polyether-based polymers, rheology-modifying polymers, dye inhibition polymers and soil release polymers as defined in more detail in paragraphs

[3035] to

[3044] of Reference RF2.Polymers may include, without limitation, "multifunctional alkoxylated polyethylene imines”, "multifunctional alkoxylated diamines” and also terephthalic acid-based polyesters like Clariant's TexCare®, such as TexCare® SRN 170, TexCare® SRN 172, TexCare® SRN 260, TexCare® SRN 260 SG Terra and TexCare® SRA 300 as well as distinct combinations of all of the before mentioned polymers. Also included are graft polymers comprising a polyalkylene oxide-based backbone with grafted side chains of vinyl ester monomer and optionally N- vinylpyrrolidone monomers.In preferred embodiments, the cleaning compositions comprise the inventive surfactant(s) and an additional surfactant or surfactant system. "(Additional) surfactants” are anionic, non-ionic, cationic, amphoteric and zwitterionic surfactants defined in more detail in paragraphs

[3008] to

[3034] of Reference RF2. In addition, these surfactants are also described in more detail in paragraphs

[0008] to

[0013] of Reference RF1.Anionic surfactants for inventive cleaning compositions include linear alkylbenzenesulfonates (LAS), alkyl sulfates (AS), alkyl alkoxy sulfates (AES), alkyl alkoxy carboxylates, modified alkylbenzene sulfonate (MLAS), methyl ester24107415 sulfonate (MES), alkyl sulfosuccinates, alpha-olefin sulfonate (AOS), alkyl polyglycosides (APG) and biosurfactants, such as rhamnolipids and sophorolipids. Non-ionic surfactants for inventive cleaning compositions include alkoxylates, alkoxylated alcohols, alkoxylated fatty acids and alkoxylated (poly-)saccharides. Cationic surfactants for inventive cleaning compositions include surfactants comprising a quaternary ammonium. Amphoteric surfactants for inventive cleaning compositions include amine oxides. Zwitter-ionic surfactants for inventive cleaning compositions include betaines.In preferred embodiments, the cleaning compositions comprise the inventive surfactant(s) and a builder. "Builders” are defined in more detail in paragraphs

[0014] to

[0018] of Reference RF1. These builders include non-phosphate- based builders (NPB) and phosphonates (CoP) described in more detail in paragraphs

[3001] to

[3005] of Reference RF2.Builders may include, without limitation, methylglycinediaceticacid (MGDA), ethylenediaminedisuccinic acid (EDDS), glutamic acid diacetate (GLDA), citric acid and salts thereof.In preferred embodiments, the cleaning compositions comprise the inventive surfactant(s) and an enzyme. "Enzymes” are defined in more detail in paragraphs

[0020] to

[0027] of Reference RF1.Enzymes may include hydrolases, such as proteases, amylases, lipases, DNases, cellulases, hemicellulases, phospholipases, esterases, mannanases, xylanases, dispersins, oxidoreductases, cutinases, pectate lyases, pectinases, lactases and peroxidases. In more preferred embodiments, the cleaning composition comprises, in addition to the inventive compound(s), a protease and a protease stabilizing system comprising a peptide aldehyde.In preferred embodiments, the cleaning compositions comprise the inventive surfactant(s) and a biocide. "Biocides” are defined in more detail in paragraphs

[0035] and

[0036] of Reference RF1. These biocides also include compounds as defined in more detail in paragraphs

[3006] and

[3007] of Reference RF2.Biocides may include, without limitation, 2-phenoxyethanol and 4,4'-dichoro 2-hydroxydiphenylether.Further adjunct cleaning additives are included and described in more detail in paragraphs

[0005] ,

[0006] ,

[0019] ,

[0028] to

[0031] and

[0037] to

[0039] of Reference RF1.Liquid laundry formulations, solid laundry compositions, liquid manual dish wash formulations, automatic dish wash (ADW) gels and automatic dish wash (ADW) solid compositions comprising inventive surfactant(s) are defined in more detail in paragraph

[0042] of Reference RF1.241074ExamplesI) Synthesis:GeneralA long-chain aliphatic fatty acid chloride is dissolved in acetone and added to an aqueous solution of a ringcomprising amino acid in presence of potassium carbonate. After work-up, the obtained products show an acylation degree of at least 90%. Optionally, fatty acid, which is generated by hydrolysis of the fatty acid chloride, is removed by distillation.Inventive example (IE)I E1 : N-cocoylproline sodium salt : N-cocoylglutamate sodium salt = 95 : 5C11 H23 / C13H2795% w / w N-cocoylproline sodium salt : 5% w / w : N-cocoylglutamate sodium salt (each with R' = C11H23 1 C13H27 = 75 / 25)I) L-Proline (Pyrrolidine-2-carboxylic acid, 10.5 g, 91 mmol, 1 eq) and potassium carbonate (39.2 g, 283 mmol, 3.1 eq) was dissolved in water (400 ml) in a 750 ml vessel and cooled to 0 °C. A mixture of lauroyl chloride (n-dodecanoic acid chloride, 15.0 g, 69 mmol, 0,75 eq) and myristoyl chloride (n-tetradecanoic acid chloride, 5.6 g, 23 mmol, 0.25 eq) in acetone (200 ml) was added dropwise at -1 - 2°C within 30 minutes. Reaction mixture was stirred and warmed to 22°C within 180 minutes. Acetone was removed under mellow temperature and reduced24107417 pressure (32°C, 100 mbar), the remaining solution was acidified to pH = 1 with concentrated HCI (58.6 g). The mixture was extracted 3 times using ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under mellow temperature and reduced pressure (32°C, 6 mbar), the residue was solved in ethanol (200 ml). A solution of sodium hydroxide (4.0 g) in ethanol (100 ml) was added and the mixture was stirred for 30 minutes. Ethanol was removed under mellow temperature and reduced pressure (32°C, 6 mbar). The slightly yellowish, waxlike product was analyzed by proton NMR spectroscopy and structure was confirmed.In case of larger amounts (>10 mol%) of fatty acid as by-product one can purify the compound in the following way:The crude product was acidified with HCI (pH = 1) and then purified by a "Kugelrohr” distillation. To separate N- cocoyl proli nic acid and cocoyl acid (mixture of 0.75 eq dodecanoic acid and 0.25 eq tetradecanoic acid) the product mixture (25 g with 20-30 mol% of cocoyl acid) was pre-distilled on a rotary evaporator at 50°C and 6 mbar. Then, the mixture was filled in the terminal bulb of the "Kugelrohr” and the pressure was reduced to 0.2 mbar. The tube furnace was heated to 120°C and the temperature was further increased up to 190°C. The remaining product in the terminal bulb (17.2 g) was dissolved in water and sodium hydroxide was added to adjust the pH to 7. The solution comprises 20 wt% surfactant in water. The product was analyzed by proton NMR spectroscopy and structure was confirmed.II) Glutamic acid (2-Aminopentanedioic acid, 13 g, 88.4 mmol, 1 eq) and potassium carbonate (37.9 g, 274 mmol, 3, 1 eq) was dissolved in water (400 ml) in a 750 ml vessel and cooled to 0 °C. A mixture of lauroyl chloride (n-Dodecanoic acid chloride, 14.5 g, 66.3 mmol, 0.75 eq) and myristoyl chloride (n-tetradecanoic acid chloride, 5.5 g, 22.1 mmol, 0.25 eq) in acetone (200 ml) was added dropwise at -1 - 2°C within 30 minutes. Reaction mixture was stirred and warmed to 22°C within 180 minutes. Acetone was removed under mellow temperature and reduced pressure (32°C, 100 mbar), the remaining solution was acidified to pH = 1 with concentrated HCI (52.8 g). The mixture was extracted 3 times using ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under mellow temperature and reduced pressure (32°C, 6 mbar). The crude product is recrystallized two times in toluene (50 ml) and solved in ethanol (100 ml). A solution of sodium hydroxide (7 g) in ethanol (100 ml) was added and the mixture was stirred for 30 minutes. Ethanol was removed under mellow temperature and reduced pressure (32°C, 6 mbar). The crystalline, white product was analyzed by proton NMR spectroscopy.In case of larger amounts (>10 mol%) of fatty acid as by-product one can purify the compound in the following way:The crude product was acidified with HCI (pH = 1) and then purified by a "Kugelrohr” distillation. To separate N- Cocoylglutamic acid and cocoyl acid (mixture of 0.75 eq dodecanoic acid and 0.25 eq tetradecanoic acid) the product mixture (26 g with 20-30 mol% of cocoyl acid) was pre-distilled on a rotary evaporator at 50°C and 6 mbar. Then, the mixture was filled in the terminal bulb of the "Kugelrohr” and the pressure was reduced to 0.2 mbar. The tube furnace was heated to 120°C and the temperature was further increased up to 190°C. The remaining product in the terminal bulb (18 g) was dissolved in water and sodium hydroxide was added to adjust the pH to 7. The24107418 solution comprises 20 wt% surfactant in water. The product was analyzed by proton NMR spectroscopy and structure was confirmed.N-cocoylprolin sodium salt (5.97 g, 95 wt%) and N-cocoylglutamic sodium salt (0.28 g, 5 wt%) where dissolved in the exact amount of water (23.87 g) that was needed to yield a clear solution comprising 20 wt% of active content.The above mixture is called the Inventive Example 1 (IE1).Comparative examplesCE2: N-Cocoyllysine sodium saltNaLysine (2,6-Diaminohexanoic acid, 20.0 g, 137 mmol, 1 eq) and potassium carbonate (58.6 g, 424 mmol, 3.1 eq) was dissolved in water (600 ml) in a 1 ,000 ml vessel and cooled to 0 °C. A mixture of lauroyl chloride (n-dodecanoyl chloride, 22.5 g, 103 mmol, 0.75 eq) and myristoyl chloride (n-tetradecanoyl chloride, 8.4 g, 34.2 mmol, 0.25 eq) in acetone (300 ml) was added dropwise at -1 - 2°C within 30 minutes. Reaction mixture was stirred and warmed to 22°C within 180 minutes. Acetone was removed under mellow temperature and reduced pressure (32°C, 100 mbar), the remaining solution was acidified to pH = 1 with concentrated HCI (58.7 g). The precipitate that formed was collected using vacuum filtration, washed with water, dried and solved in ethanol (500 ml). A solution of sodium hydroxide (3.8 g) in ethanol (100 ml) was added and the mixture was stirred for 30 minutes. Ethanol was removed under mellow temperature and reduced pressure (32°C, 6 mbar). The product was dissolved in water to obtain a solution of 20 wt% surfactant in water.24107419CE3: C12C14 - 2 EO - SO4NaThe well-known detergent surfactant alkyl ether sulfate (AES) sodium salt C12C14 - 2 EO - SC^Na (commercially sold as Texapon N70) was used for comparative studies. The C12C14 alkyl chain is linear and saturated. The average carbon number is around 12.5 carbon atoms in the alkyl group. A linear C12C14 fatty alcohol is reacted with ca. 2 eq of ethylene oxide by use of KOH catalysis. The obtained alkyl ethoxylate is sulfated with sulfur trioxide in a falling film reactor (sulfation degrees are 90% and higher). The intermediate semi sulfuric acid ester C12C14- 2EO-OSO3H is then neutralized with a base. In this case it was neutralized with NaOH.II) Functional tests:The amounts and concentrations of surfactants in the following tests refer to active material.A) Wetting timeAs shown for IE1 in Table 1 , the inventive surfactants wet a cotton rag in 26 seconds at 20°C (test according to EN 1772, cotton rag is put below surface of aqueous surfactant solution, once the rag is fully wetted and air is released from cotton rag it starts to sink to the bottom; the time is noted once the cotton rag starts to sink). The comparative example CE2 based on lysine requires more than 300 seconds and is a very bad wetter. The detergent surfactant alkyl ether sulfate sodium salt C12C14 - 2 EO - SO4Na (45 seconds in comparative example CE3) also needs significantly longer than the inventive surfactants. The inventive surfactants are almost two-times faster to fully wet a cotton rag.Table 1 : Wetting of cotton rag at 20°C in hard water (10 °dH)B) FoamabilityAs shown in table 2, inventive compounds of IE1 show a much better foamability (450 ml in inventive example IE1) at 40°C in hard water (10° dH) using 2 g of material per liter in a test regarding whipped foam (EN 12728, DIN 53902) compared to other, acyclic, modified amino acids, such as N-Cocoyllysine sodium salt (30 ml in comparative example CE2). The detergent surfactant alkyl ether sulfate sodium salt C12C14 - 2 EO - SO4Na shows the best foamability (725 ml in comparative example CE3), however, the inventive structures (inventive example IE1) are surprisingly close regarding foamability. A good foamability is of interest e.g., for hand dishwashing in presence of hardness (such as calcium ions).24107420Table 2 Foamability of 2 g surfactant per liter of hard water (10° dH) at 40°C using whipped foam methodC) Dynamic surface tensionTable 3 underlines that the inventive structures (I E1) show after 0.1 seconds in hard water a much lower dynamic surface tension (43.1 mN / m in inventive example IE1 ) compared to other, acyclic, modified amino acids such as N- Cocoy llysine sodium salt (68.7 mN / m in comparative example CE2). Such lower dynamic surface tension indicates that the surfactant is fast at interfaces e.g., at oil-water interface and can start the removal of e.g., oil earlier. This is of relevance for l&l processes, laundry, and dishwashing. The detergent surfactant alkyl ether sulfate sodium salt C12C14 - 2 EO - SC>4Na shows an even slightly lower dynamic interfacial tension (42.1 mN / m in comparative example CE3), however the inventive structures (inventive example IE1) are surprisingly close to a commercial standard cleaning surfactant regarding dynamic interfacial tension.Table 3 Dynamic surface tension of 1 g surfactant per liter of hard water (10° dH) at room temperature after 0.1 sD) Interfacial tensionTable 4 describes that inventive structures (IE1) show in hard water after 3 minutes lower interfacial tension against olive oil or n-hexadecane (0.21 mN / m and 1.09 mN / m in inventive example IE1) compared to other, acyclic, modified amino acids such as N-Cocoyllysine sodium salt (11 mN / m and 4.3 mN / m in comparative example CE2). Such lower interfacial tension indicates that the surfactant can remove oil in a better way. Olive oil is a triglyceride and thereby a model oil for soil in laundry or dishwashing; n-hexadecane is a model oil for aliphatic oils e.g., from the lubricant sector. This is of relevance for l&l processes, laundry, and dishwashing. A comparison with detergent surfactant alkyl ether sulfate sodium salt C12C14 - 2 EO - SO4Na (0.6 mN / m and 0.8 mN / m in comparative example CE3) shows that the inventive structures (inventive example IE1) are on the same level regarding interfacial tension or even lower.24107421Table 4 Interfacial tension of 1 g surfactant per liter of hard water (10° dH) at room temperature after 3 minE) Mineral oil removalTable 5 underlines that the inventive surfactants (IE1) show in hard water a better removal of mineral oil from a copper surface after 25 minutes (73.9% of oil removed in example IE1) compared to other, acyclic, modified amino acids such as N-Cocoyllysine sodium salt (40.3% of oil in comparative example CE2). The detergent surfactant alkyl ether sulfate sodium salt C12C14 - 2 EC - SO4Na (69.9% of oil in comparative example CE3) removes less oil than the inventive surfactants.Table 5: Mineral oil removal from copper surface by use of 1 g surfactant per liter of hard water (10° dH) at pH = 9 and at room temperature after 25 minF) BiodegradabilityTable 6 shows a significant biodegradability of 81 % within 28 days under aerobic conditions using a sludge from a communal sewage plant in Germany for the inventive surfactants IE1. Test conditions according to OECD 301 F were used as described above. The value of 81 % within 28 days fulfills the requirement of min. 60% within 28 days for a detergent surfactant.Table 6: Biodegradability within 28 days under aerobic conditions with sludge from communal sewage plant24107422G) Washtests including enzymesThe washing test was conducted with a protease (Lavergy Pro 114 LS was used as protease). Following detergent formulations were prepared on weight basis. Beside the previously described inventive surfactant mixture, detergent surfactants such as C10-C13-Ph-SO3H (Maranil DBS / LC from BASF), C13C15 - 7 EO (Lutensol AO7 from BASF), and 012014 - 2 EO - S04Na (Texapon N70) were used. The surfactant amounts in formulation table below refer to active material. The rest is as is. Edenor K 12-18 (from KLK Oleo) is a mixture of fatty acids with 12 to 18 carbon atoms. Formulation E is another example for a typical detergent formulation. Formulation F is Formulation E without the alkyl ether sulfate. Formulation G is Formulation F with the inventive surfactant mixture (N-cocoylproline sodium salt : N-cocoylglutamate sodium salt = 95 : 5 (as described above each with R' = C11 H23 / C13H27 = 75 / 25, and M+= Na+, IE1). Formulation H is Formulation F with the comparative surfactant (N- Cocoyllysine sodium salt, CE2).The washing performance was determined as follows:The L*, a* b* values of the single stains on multi soil monitors are measured before wash with a MACH 5 from CFT / Color consult. Then the fabrics are washed together with cotton ballast fabric and 20 steel balls at 30°C in water with defined water hardness. After the wash the fabrics are rinsed, spin-dried and dried in the air.24107423The washing performance for the single stains is determined by measuring the L*, a* b* values with a MACH 5 from CFT / Color consult after drying. The dE value is calculated from the single values before and after wash. The 2 stains from the monitor are summed up. The higher the value, the better the performance. The experiment was repeated, and the average values were used. The stains cover typical kinds of soil, which are addressed by a protease: egg and blood.Washing conditions:Producer: wfk-Testgewebe, Christenfeld 10, 41379 Briiggen; Swissatest Testmaterialien AG, MbvenstraBe 12, CH-9015 St. Gallen; Center for Testmaterials B.V., Stoomloggerweg 11 , NL-3133 VlaardingenTable 7 shows result of detergency with a protease in a launder-o-meter test at 30°C using each 2 stains on fabric (CFT-C-S-01, CFT-C-S-39), 3 g / l formulation and water with hardness of 2.5 mmol. Steel balls were added to simulate impact of mechanics and fabric was washed for 60 minutes. Remission of fabric before and after washing was detected and difference (in DE) was noted. As shown in example IE1 , the formulation G with the inventive surfactant mixture IE1 (48.1 delta E values at 30°C) removes the 2 stains much better than the formulation E comprising the classical detergent surfactant alkyl ether sulfate (47.3 delta E values at 20°C). At 30°C, the inventive surfactant IE1 (48.1 delta E values at 30°C) is surprisingly much better than the comparative surfactant CE2 (Formulation H, 43.4 delta E values at 30°C). Formulation F provides even a better stain removal (47.3 delta E values at 30°C) than the comparative surfactant CE2. It is noted that the inventive surfactant mixture is provides a good cleaning results at low washing temperature of 30°C compared to standard surfactant. This provides a solution for dioxane-free detergent formulation as alkyl ether sulfates can always be a source of dioxane formation, which is at the end a contribution to sustainability.Table 7: Detergency with protease in a launder-o-meter test at 30°C using 2 stains (CFT-C-S-01 , CFT-C-S-38) on fabrics after 60 min with and without surfactant in hard waterThe next washing test was conducted with an amylase (Lavergy A Star was used as amylase). Following detergent formulations were prepared on weight basis. Beside the previously described inventive surfactant mixture, detergent surfactants such as C10-C13-Ph-SO3H (Maranil DBS / LC from BASF), C13C15 - 7 EO (Lutensol AO7 from BASF), and C12C14 - 2 EO - SO4Na (Texapon N70) were used. The surfactant amounts in formulation table below refer to active material. The rest is as is. Edenor K 12-18 (from KLK Oleo) is a mixture of fatty acids with 12 to 18 carbon atoms. Formulation I is another example for a typical detergent formulation. Formulation J is Formulation I without the alkyl ether sulfate. Formulation K is Formulation J with the inventive surfactant mixture (N-cocoylproline sodium salt : N-cocoylglutamate sodium salt = 95 : 5 (as described above each with R' = C11 H23 / C13H27 = 75 / 25, and M+= Na+), IE1). Formulation L is Formulation J with the comparative surfactant N- Cocoy llysine sodium salt, CE2).25The washing performance was determined as follows:The L*, a* b* values of the single stains on multi soil monitors are measured before wash with a MACH 5 from CFT / Color consult. Then the fabrics are washed together with cotton ballast fabric and 20 steel balls at 30°C in water with defined water hardness. After the wash the fabrics are rinsed, spin-dried and dried in the air.The washing performance for the single stains is determined by measuring the L*, a* b* values with a MACH 5 from CFT / Color consult after drying. The dE value is calculated from the single values before and after wash. The 2 stains from the monitor are summed up. The higher the value, the better the performance. The experiment was repeated, and the average values were used. The stains cover typical kinds of soil, which are addressed by an amylase: rice starch and starch.Washing conditions:Producer: wfk-Testgewebe, Christenfeld 10, 41379 Briiggen; Swissatest Testmaterialien AG, MbvenstraBe 12, CH-9015 St. Gallen; Center for Testmaterials B.V., Stoomloggerweg 11 , NL-3133 VlaardingenTable 8 shows result of detergency with an amylase in a launder-o-meter test at 30°C using each 2 stains on fabric (CFT-C-S-28, E-161), 3 g / l formulation and water with hardness of 2.5 mmol. Steel balls were added to simulate impact of mechanics and fabric was washed for 60 minutes. Remission of fabric before and after washing was detected and difference (in DE) was noted. As shown in example IE1 , the formulation K with the inventive surfactant mixture IE1 (63.8 delta E values at 30°C) removes the 2 stains much better than the formulation I comprising the classical detergent surfactant alkyl ether sulfate (61.7 delta E values at 30°C). At 30°C, the inventive surfactant IE1 (63.8 delta E values at 30°C) is also better than the comparative surfactant CE2 (Formulation L, 62.3 delta E values24107426 at 30°C). Formulation J provides a similar stain removal (62.3 delta E values at 30°C) than the comparative surfactant CE2. It is noted that the inventive surfactant mixture is provides a good cleaning results at low washing temperature of 30°C compared to standard surfactant. This provides a solution for dioxane-free detergent formulation as alkyl ether sulfates can always be a source of dioxane formation, which is at the end a contribution to sustainability.Table 8: Detergency with amylase in a launder-o-meter test at 30°C using 2 stains (CFT-C-S-29, CFT-C-S-129) on fabrics after 60 min with and without surfactant in hard water

Claims

24107427Claims1 . A composition comprising(1) at least one compound according to Formula (1)whereinR1 is an aliphatic, saturated or unsaturated, linear or branched moiety comprising 7 to 17 carbon atoms, and the dotted lines indicate ill) a moiety according to Formula (2) owhereinM+is selected from the group consisting of H+, Na+, K+, NH4+, protonated amine and protonated amino alcohol, or iv) bonds to the remaining parts of the compound according to Formula (1), wherein at least one remaining part comprises at least one five-membered ring and a directly bound moiety according to Formula (3); and(2) at least one compound according to Formula (3)wherein n is an integer between 1 and 5;R2 is an aliphatic, saturated or unsaturated, linear or branched moiety comprising 7 to 17 carbon atoms; and M+is as defined above.241074282. The composition according to claim 1, wherein the compound according to Formula (1) has a structure according to one formula selected from the group consisting of Formula (4) and (5):whereinM+and R1 are as defined above.

3. The composition according to claim 1 or 2 comprising a compound according to Formula (4).

4. The composition according to any one of claims 1 to 3, wherein n is 1 or 2, preferably 2.

5. The composition according to any one of claims 1 to 4, wherein R1 and R2 are independently of each other an aliphatic, saturated or unsaturated, preferably saturated, linear or branched, preferably linear moiety comprising 9 to 16, 10 to 15 or 11 to 13 carbon atoms.

6. The composition according to any one of claims 1 to 5, wherein M+is selected from the group consisting of Na+, K+and NH .

7. The composition according to any one of claims 1 to 6, wherein(I) the content of the at least one compound according to Formula (1) is at least 75 wt% of the sum of the weights of the compounds according to Formula (1) and (3), and(ii) the content of the at least one compound according to Formula (3) is at least 1 wt% of the sum of the weights of the compounds according to Formula (1) and (3).

8. The composition according to any one of claims 1 to 7, wherein(I) the content of the at least one compound according to Formula (1) ranges from 85 to 99 wt% of the sum of the weights of the compounds according to Formula (1) and (3), and24107429(ii) the content of the at least one compound according to Formula (3) ranges from 1 to 15 wt% of the sum of the weights of the compounds according to Formula (1) and (3).

9. The composition according to any one of claims 1 to 8, wherein the composition is a liquid composition.

10. The composition according to claim 9, wherein the liquid composition i) comprises Ca2+ions; and ii) comprises, by weight of the composition, from 5% to 95% of water.11 . The composition according to any one of claims 1 to 10, wherein the composition is a cleaning composition, fabric and home care product, industrial and institutional cleaning product, wetting agent, cosmetic formulation, crude oil emulsion breaker, oil recovery formulation, formulation for corn oil separation, formulation for fermentation process, flotation agent of mineral ores, pigment dispersion for ink jet inks, formulation for electro plating, formulation for emulsion polymerization, formulation for dispersions, cementitious composition, in gypsum compositions, dispersant or wetting agent or emulsifier, comprising, consisting of or essentially consisting of the composition according to any of claims 1 to 10, preferably a cleaning composition and / or fabric and home care product and / or industrial and institutional cleaning product, comprising the composition according to any of claims 1 to 10.

12. The composition according to claim 11, wherein the composition is a cleaning composition further comprising i) at least one cleaning polymer or soil release polymer, and / or ii) at least one further surfactant selected from the group consisting of anionic surfactants and / or non-ionic surfactants and / or amphoteric surfactants and / or zwitterionic surfactants and / or cationic surfactants, and / or iii) an antimicrobial agent selected from the group consisting of 2-phenoxyethanol and 4,4'-dichoro 2- hydroxydiphenylether; preferably comprising 2-phenoxyethanol in an amount ranging from 2 ppm to 5% by weight of the composition; more preferably comprising 0.1 to 2% of phenoxyethanol or preferably comprising 4,4'-dichoro 2-hydroxydiphenylether in a concentration from 0.001 to 3%, more preferably 0.002 to 1%, even more preferably 0.01 to 0.6%, each by weight of the composition, and / or iv) at least one enzyme selected from the list consisting of lipases, hydrolases, amylases, DNases, proteases, cellulases, hemicellulases, phospholipases, esterases, mannanases, xylanases, dispersins, oxidoreductases, cutinases, pectate lyases, pectinases, lactases and peroxidases, and combinations of at least two of the foregoing types, preferably selected from one or more lipases, hydrolases, amylases, proteases, cellulases, and24107430 combinations of at least two of the foregoing types, more preferably at least one enzyme being selected from proteases, and / or v) at least one compound selected from the group consisting of builders, cobuilders, structurants or thickeners, clay soil removal / anti-redeposition agents, polymeric soil release agents, dispersants such as polymeric dispersing agents, polymeric grease cleaning agents, solubilizing agents, chelating agents, enzymes, enzyme stabilizing systems, bleaching compounds, bleaching agents, bleach activators, bleach catalysts, brighteners, malodor control agents, pigments, dyes, opacifiers, hueing agents, dye transfer inhibiting agents, chelating agents, suds boosters, suds suppressors (antifoams), color speckles, silver care, anti-tarnish and / or anti-corrosion agents, alkalinity sources, pH adjusters, pH-buffer agents, hydrotropes, scrubbing particles, antibacterial agents, anti-oxidants, softeners, carriers, processing aids, pro-perfumes, dye fixation agent and perfumes, vi) cosolvent selected from groups of aliphatic alcohols, diols (preferably propylene glycole), or triols comprising 2 to 5 carbon atoms or selected from group of ethylene glycole or diethylene glycol mono alkyl ether comprising 2 to 5 carbon atoms in alkyl moiety or selected from group of propylene glycole or dipropylene glycol mono alkyl ether comprising 2 to 5 carbon atoms in alkyl moiety, and / or vii) water.

13. Use of the composition according to any one of claims 1 to 10 in cleaning compositions, in fabric and home care products, in institutional and industrial cleaning products, in cosmetic formulations, as crude oil emulsion breaker, as surfactant in enhanced oil recovery, as surfactant in corn oil separation, as surfactant in fermentation processes, as surfactant in flotation of mineral ores, in pigment dispersions for inkjet inks, in formulations for electro plating, formulation for emulsion polymerization, formulation for dispersions, in cementitious compositions, in gypsum compositions, as dispersant or wetting agent or emulsifier.

14. The use according to claim 13 in cleaning compositions and / or in fabric and home care products, preferably in cleaning compositions forI) improved removal of oily / fatty stains, and / orII) improved removal of sebum, and / or ill) clay removal, and / or iv) soil removal of particulate stains, and / or v) dispersion and / or emulsification of soils, and / or vi) modification of treated surface to improve removal upon later re-soiling, and / or vii) whiteness improvement and / or preferably in cleaning compositions for removal of oily / fatty stains,24107431 each of the before mentioned options i) to vii) preferably for use in a laundry detergent formulation and / or a manual dish wash detergent formulation and / or in a formulation suitable for (pre)-treatment of textiles and / or soap bars, more preferably in a liquid laundry detergent formulation and / or a liquid manual dish wash detergent formulation.

15. A cleaning method comprising contacting a cleaning composition according to any one of claims 1 to 10 with an object that requires cleaning, preferably a laundry or a hard surface household item.

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