Pipecolic acid-based surfactants and their use

Abstract

Pipecolic acid-based surfactants and their use This invention deals with pipeolic acid-based surfactants and their uses, for example in laundry or dishwashing.

Description

240630W0011Pipecolic acid-based surfactants and their useThis invention deals with specific surfactants, namely pipecolic acid-based surfactants (in this present invention abbreviated as "inventive compound(s)”, "compound(s) of the invention”, "inventive surfactant(s)” or "N-acylated pipecolic acid(s)” whenever the inventive compounds are meant) as described in more detail herein, their uses and compositions including the inventive compounds, 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) 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 acylated amino acid-based surfactants, including acylated pipecolic acid-based surfactants.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 pipecolic acid, picolinic acid and similar compounds is given.240630W0012Devi et al. (Devi et al., Scientific Reports volume 5, Article number: 9950 (2015)) disclose picolinic acid derivatives. In contrast to the compounds of the present invention, the carbonyl group of the picolinic acid is converted into an amide. The amide group is not able to carry a negative charge. Therefore, the compounds described by Devi et al. cannot be used as anionic surfactants.US6194442 B1 and Biosynth, UK (https: / / www.biosvnth.eom / p / FP36586 / 2459-07-6-2-picolinic-acid-methyl-ester) disclose derivatives of picolinic acid wherein the carbonyl group has been esterified and contains short alkyl groups (C1 to C6). These compounds are not described as surfactants in cleaning compositions, but are intended to be used in pharmaceutical applications, such as initiating an anti-inflammatory response by increasing the levels of interleukin and / or tumor necrosis factor (TNF) or inhibiting integrase of HIV.Catton, G.R. (Catton, G.R., 2007, PhD Thesis, University of St. Andrews, Mechanistic Studies on Quinolinate Phosphoribosy Itransferase) discloses N-alkylnicotinic acids (see compounds 59 and 60) and N-alkylpicolinic acids (see compounds 50 and 51). These compounds contain short organic groups (methyl or ethyl groups) and are therefore not expected to demonstrate significant surface activity.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, N-cocoyllysine sodium salt shows significantly weaker surface activity than N-acylated pipecolic acid.The present inventors surprisingly found that N-acylated pipecolic acid as disclosed herein provide significantly better surface activity than other N-acylated amino acids, such as N-acylated lysine. Even when being compared with the well-known detergent surfactant alkyl ether sulfate sodium salt (AES) N-acylated pipecolic acid demonstrates comparable or even better results in terms of surface activity and wash performance. The inventive compounds can be based on non-fossil carbon sources (e.g. picolinic acid is a product of the kynurenine pathway and as a metabolite it may be fermentatively derived from eukaryotes, such as Dictyostelium, Aspergillus, Neurospora, Saccharomyces, Ustilago etc.) and show a significant degree of biodegradability.Therefore, the object of the present invention is to provide a novel compound having a structure according to Formula (1) or Formula (2)240630W0013 whereinR' is an aliphatic, saturated or unsaturated, linear or branched moiety comprising 8 to 17 carbon atoms, and the dotted linesI) are a moiety according to Formula (3) owhereinM+is selected from the group consisting of H+, Na+, K+, NH4+, protonated amine and protonated amino alcohol, or ii) indicate bonds to the remaining parts of the compound, wherein at least one remaining part comprises at least one six-membered ring and a directly bound moiety according to Formula (3) and optionally an -OH group.In another aspect, the invention is directed to a composition, preferably a cleaning composition, comprising the inventive N-acylated pipecolic acid.Further, the invention is directed to a process to prepare the inventive compounds.Moreover, in further aspects 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 16 as defined and further explained with further embodiments hereinafter and further exemplified in the experimental section:Embodiment 1A compound having a structure according to Formula (1) or Formula (2)R' is an aliphatic, saturated or unsaturated, linear or branched moiety comprising 8 to 17 carbon atoms, and the dotted lines are a moiety according to Formula (3)240630W001 o 4whereinM+is selected from the group consisting of H+, Na+, K+, NH4+, protonated amine and protonated amino alcohol, or ii) indicate bonds to the remaining parts of the compound, wherein at least one remaining part comprises at least one six-membered ring and a directly bound moiety according to Formula (3) and optionally an -OH group.The compounds of Formula (1) and Formula (2) are or are based on pipecolic acid and / or nipecotic acid and can thus be derived from picolinic acid. Picolinic acid is an organic compound with the formula C5H4NCOOH. It is a derivative of pyridine with a carboxylic acid (COOH) substituent at the 2-position. Alternatively, it can be described as an isomer of nicotinic acid and isonicotinic acid, which have the carboxyl side chain at the 3- and 4-positions, respectively. Picolinic acid may also be named Pyridine-2-carboxylic acid. Its CAS number is 98-98-6 and can be obtained commercially, e.g. from Sigma-Aldrich, St. Louis, USA. Pipecolic acid is the aliphatic equivalent to picolinic acid (formally obtained by hydrogenation of the aromatic ring). Nipecotic acid is the aliphatic equivalent to nicotinic acid (formally obtained by hydrogenation of the aromatic ring).Fermentation of picolinic acid and subsequent extraction has been described by Kumar et al. (Kumar, S.; Datta, D.; Babu, B. V. J. Chem. Eng. Data 2010, 55, 4290- 4300) and Kertes and King (Kertes, A. S.; King, C. J. Biotechnol. Bioeng. 1986, 28, 269- 282). Thus, the skilled person is well-aware of different synthesis pathways for picolinic acid, wherein the educts are based on fossil and / or non-fossil carbon atoms. In preferred embodiments, at least 10%, at least 20%, at least 40%, at least 70%, at least 95% or even 100% of the carbon atoms in the part derived from picolinic acid (or pipecolic acid) or even in the whole inventive compound are non-fossil derived carbon atoms. Pipecolic acid can also be obtained by conversion of lysine e.g. in an enzymatic or fermentation process.The term "aliphatic, saturated or unsaturated, linear or branched moiety”, as used herein, means a straight-chain (i.e., unbranched, linear) or branched, substituted or unsubstituted hydrocarbon chain that is completely saturated or that contains one or more units of unsaturation, or a monocyclic hydrocarbon or bicyclic hydrocarbon that is completely saturated or that contains one or more units of unsaturation, but which is not aromatic (also known as "carbocycle” , "cycloaliphatic” or "cycloalkyl” ) that has a single point of attachment to the rest of the inventive compound. Unless otherwise specified, aliphatic groups contain aliphatic carbon atoms. Suitable aliphatic groups include, but are not limited to, linear or branched, substituted or unsubstituted alkyl, alkenyl, alkynyl groups and hybrids thereof such as (cycloalkyl) alkyl, (cycloalkenyl) alkyl or (cycloalkyl) alkenyl. The term "substituted”, as used herein, means that a hydrogen and / or carbon atom in the hydrocarbon chain is replaced with O, S, N, P and / or Si.240630W0015In preferred embodiments, only one of the dotted lines indicate a moiety according to Formula (3). In more preferred embodiments, the moiety according to Formula (3) is in ortho or meta position relative to the nitrogen atom. In even more preferred embodiments, the moiety according to Formula (3) is in ortho position relative to the nitrogen atom.The term "at least one six-membered ring”, as used herein, means that the inventive compounds may comprise additional six-membered rings compared to the one shown in Figures (1) and (2). In preferred embodiments, the inventive compounds have no or one or two additional ring structures compared to the one shown in Figure (1) or (2). These additional six-membered rings may contain one nitrogen atom and five carbon atoms. The term "moiety according to Formula (3) directly bound to the six-membered ring” or derivatives thereof, as used herein, means that the carbon atom of the carbonyl group according to Formula (3) is covalently to a carbon atom of the additional six-membered ring."Protonated 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.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.Embodiment 2The compound according to Embodiment 1 , wherein the compound has a structure according to one formula selected from the group consisting of Formula (4) to (13):(7) (8)240630W0016M+and R' are as defined above.Embodiment 3The compound according to Embodiment 1 or 2, wherein R' is 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 4The compound according to any one of Embodiments 1 to 3, wherein M+is Na+, K+or NH4+.240630W0017Embodiment 5The compound according to anyone of Embodiments 1 to 4, wherein said inventive pipecolic acid-based surfactant or inventive nipecotic acid-based surfactant demonstrates at least 60%, preferably at least 65% or more preferably at least 70% biodegradability according to standard OECD 301 F after 56 days, preferably after 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 compound 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.Embodiment 6A composition, 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, formulation for emulsion polymerization, formulation for dispersions, comprising, consisting of or essentially consisting of the compound according to any of Embodiments 1 to 5, preferably a cleaning composition and / or fabric and home care product and / or industrial and institutional cleaning product, comprising the compound according to any of Embodiments 1 to 5.The terms "essentially consisting of' or "consisting essentially of', as used interchangeably herein, with respect to the N-acylated pipecolic acid composition mean that the composition may comprise impurities or other types of N- acylated pipecolic acid 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.A subject matter of the present invention is the use of the above-mentioned N-acylated pipecolic acid and derivatives thereof in fabric and home care products, in cosmetic formulations, as crude oil emulsion breaker, oil recovery formulation, formulation for corn oil separation, formulation for fermentation process, flotation agent of mineral ores, pigment dispersion for inkjet inks, formulation for electro plating, cementitious composition, in gypsum compositions, dispersant or wetting agent or emulsifier, formulation for emulsion polymerization, formulation for dispersions, preferably in cleaning compositions and / or in fabric and home care products, in particular cleaning240630W0018 compositions for improved sebum 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 N-acylated pipecolic acid 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, formulations for emulsion polymerization, formulations for dispersions. However, the inventive compounds 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, as 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, formulation for emulsion polymerization, formulation for dispersion, comprising at least one N-acylated pipecolic acid, as defined above.Preferably, it is a cleaning composition and / or fabric and home care product, comprising at least one N-acylated pipecolic acid, as defined above, preferably for oily and fatty stain removal, or sebum and body soil 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 N-acylated pipecolic acid 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.240630W0019In this invention, a preferred area of application for the use of the N-acylated pipecolic acid 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.All of the terms within Embodiment 6 have already been defined and explained in detail herein before within the description of the Embodiments 1 to 5, such terms, definitions and further specifications of course apply to this Embodiment 6.Embodiment 7The composition according to Embodiment 6, 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 8The composition according to Embodiment 7, 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.In 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 9240630W00110The composition according to any one of Embodiments 6 to 8, 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 ill) 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, 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.240630W00111In alternatively preferred embodiments, the cleaning composition of the invention does not comprise further(anionic) surfactants in addition to the N-acylated pipecolic acid compound(s).Embodiment 10The composition according to any one of Embodiments 6 to 9, wherein said composition comprises a mixture of at least two compounds according to any of Embodiments 1 to 5. Preferably, the inventive composition comprises a mixture of at least two compounds selected from the group of compounds according to Formula (4) to (13).Embodiment 11The composition according to Embodiment 10, wherein the mixture is selected from a group consisting of(i) a mixture of compounds according to Formula (4) and (9);(ii) a mixture of compounds according to Formula (5) and (10);(iii) a mixture of compounds according to Formula (6) and (11);(iv) a mixture of compounds according to Formula (7) and (12); and(v) a mixture of compounds according to Formula (8) and (13).Embodiment 12Use of the compound according to any one of Embodiments 1 to 5 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 cementitious compositions, in gypsum compositions, as dispersant or wetting agent or emulsifier, in formulations for emulsion polymerization or formulations for dispersions.All of the terms within Embodiment 12 have already been defined and explained in detail herein before within the description of the Embodiments 1 to 11, such terms, definitions and further specifications of course apply to this Embodiment 12.Embodiment 13The use according to Embodiment 12 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 / or v) dispersion and / or emulsification of soils, and / or240630W00112 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 14A cleaning method comprising contacting a cleaning composition according to any one of Embodiments 6 to 11 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.All of the terms within Embodiment 14 have already been defined and explained in detail herein before within the description of the Embodiments 1 to 13, such terms, definitions and further specifications of course apply to this Embodiment 14.Embodiment 15A process to prepare the compound according to any one of Embodiments 1 to 5 comprising reacting a compound according to Formula (14) o(14), wherein R' is an aliphatic, saturated or unsaturated, linear or branched moiety comprising 8 to 17 carbon atoms with a compound according to Formula (15) or Formula (16)240630W001wherein the dotted lines i) are a moiety according to Formula (3) as described above, or ii) indicate bonds to the remaining parts of the compound, wherein at least one remaining part comprises at least one six-membered ring and a directly bound moiety according to Formula (3) and optionally an -OH group.All of the terms within Embodiment 15 have already been defined and explained in detail herein before within the description of the Embodiments 1 to 5, such terms, definitions and further specifications of course apply to this Embodiment 15.In preferred embodiments, the reaction step of the process to prepare the inventive compounds comprises the presence of sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate, or potassium carbonate.The conversion rate of the reaction step may be monitored and in preferred embodiments the conversion rate for this step is at least 85%, at least 90%, at least 95%, preferably at least 99%, and even more preferably at least 99,5 % or even more.The conversion rate of the reaction can be determined according to methods known to the skilled person, such as HPLC, and NMR-spectroscopy, such as 13C-NMR-spectroscopy and / or 1 H NMR-spectroscopy.Embodiment 16Process according to Embodiment 15, wherein the N-acylated pipecolic acid is further submitted to the following process steps of a. purification using standard means such as steam distillation, thermal distillation, vacuum evaporation, including removal of all solvent, dialysis and / or b. drying using standard drying means such as spray-, drum, paddle-, vacuum-drying means including agglomeration methods such as fluidized-bed-drying, to obtain a purified solution, a purified liquid, a solid compound or a purified solid compound, respectively.240630W00114In case that after the reactions leading to the inventive compound residual educts (pipecolic acid, pipecolic acid derivative or fatty acid) are present to a non-desirable extent, the resulting product mixture containing the N- acylated pipecolic acid may be further purified by standard means to reduce the content of residual educts, but also to reduce the amount of possible by-products, reduce the amount(s) of the solvent(s) employed (i.e., to concentrate) or replace solvent(s) with other solvents. Such processes are known to a person of skill in this field.Preferably, undesirable amounts of residual non-reacted educts are removed, preferably by means of distillative processes, more preferably by thermal distillative processes, which may additionally comprise the application of reduced pressure to increase the speed and / or the effectiveness of the removal.In a preferred embodiment only the additional process step a) is employed.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.The 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 include240630W00115 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."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 RF1.240630W00116The 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 anticorrosion 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 ester 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.240630W00117Amphoteric 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.ExamplesI) Synthesis:240630W00118GeneralA 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)IE1 : N-Lauroylpipecolinate sodium salt N-Myristoylpipecolinate sodium salt = 75 25(la with R' = Ci 1 H23 / C13H27 = 751 25, and M+= Na+)Pipecolic acid (Piperidine-2-carboxylic acid, 13.3 g, 103 mmol, 1 eq) and potassium carbonate (44.2 g, 319 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, 16.9 g, 77 mmol, 0.75 eq) and myristoyl chloride (n-tetradecanoic acid chloride, 6.4 g, 26 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 (81.1 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 (150 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 of fatty acid (>10 mol%) 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- Cocoylpipecolic acid (N-Cocoyl piperidine-2-carboxylic acid) and cocoyl acid (mixture of 0.75 eq dodecanoic acid and 0.25 eq tetradecanoic acid) the product mixture (24.7 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 (17.5 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.240630W00119(Ila with R' = Ci 1 H23 / C13H27 = 751 25, and M+= Na+)Nipecotic acid (3-Piperidincaboxylic acid, 15 g, 116 mmol, 1 eq) and potassium carbonate (49.8 g, 360 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, 19.1 g, 87 mmol, 0.75 eq) and myristoyl chloride (n-tetradecanoic acid chloride, 7,2 g, 29 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 (62.0 g). The white precipitate that formed was collected using vacuum filtration, washed with water, dried and solved in ethanol (200 ml). A solution of sodium hydroxide (4.0 g) in ethanol (150 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- Cocoylnipecotic acid (N-Cocoyl piperidine-3-carboxylic acid) and cocoyl acid (mixture of 0.75 eq dodecanoic acid and 0.25 eq tetradecanoic acid) the product mixture (24.5 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 (17.6 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.Comparative examplesCE4: N-Cocoyllysine sodium salt240630W00120NaLysine (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 (1.8 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.CE5: 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:240630W00121The amounts and concentrations of surfactants in the following tests refer to active material.A) Wetting timeAs shown for IE1 and IE2, in Table 1 , the inventive surfactants wet a cotton rag in 17 to 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 CE4 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 CE5) also needs significantly longer than the inventive surfactant. The inventive surfactant is 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 IE1 and IE2 show a much better foamability (640 ml in inventive example IE1, 690 ml in inventive example IE2) 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 CE4). The detergent surfactant alkyl ether sulfate sodium salt C12C14 - 2 EO - SO4Na shows the best foamability (725 ml in comparative example CE5), however, the inventive structures (inventive example IE1 and IE2) are surprisingly close regarding foamability (around 10 percent or less). A good foamability is of interest e.g., for hand dishwashing in presence of hardness (such as calcium ions).Table 2 Foamability of 2 g surfactant per liter of hard water (10° dH) at 40°C using whipped foam method240630W00122C) Dynamic surface tensionTable 3 underlines that the inventive structures (I E1 ) and (IE2) show after 0.1 seconds in hard water a much lower dynamic surface tension (43.0 mN / m in inventive example I E1 , 47.8 mN / m in inventive example IE2) compared to other, acyclic, modified amino acids such as N-Cocoyllysine sodium salt (68.7 mN / m in comparative example CE4). 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 - SO4Na shows an even slightly lower dynamic interfacial tension (42.1 mN / m in comparative example CE5), however the inventive structures (inventive example IE1, IE2) 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) and (IE2) show in hard water after 3 minutes lower interfacial tension against olive oil or n-hexadecane (0.72 MN / m and < 0.1 mN / m mN / m in inventive example IE1 , 1.3 mN / m and <0.1 mN / m in inventive example IE2) compared to other, acyclic, modified amino acids such as N-Cocoyllysine sodium salt (11 mN / m and 4.3 mN / m in comparative example CE4). 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 CE5) shows that the inventive structures (inventive example IE1 , IE2) are on the same level regarding interfacial tension or even lower.Table 4 Interfacial tension of 1 g surfactant per liter of hard water (10° dH) at room temperature after 3 min240630W00123E) Mineral oil removalTable 5 underlines that the inventive surfactants (IE1 ) and (IE2) show in hard water a better removal of mineral oil from a copper surface after 25 minutes (98.2% of oil removed in example I E1 , 78.0% of oil removed in example IE2) compared to other, acyclic, modified amino acids such as N-Cocoy I lysine sodium salt (40.3% of oil in comparative example CE4). The detergent surfactant alkyl ether sulfate sodium salt C12C14 - 2 EO - SO4Na (69.9% of oil in comparative example CE4) remove 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 minConsidering all tests results in table 1 - 5, it was decided to compare IE1, namely N-Lauroylpipecolinate sodium salt : N-Myristoylpipecolinate sodium salt = 75 : 25 (la with R' = Ci 1 H23 / C13H27 = 751 25, and M+= Na+), as well as IE2, namely N-Lauroylnipecotinate sodium salt : N-Myristoylnipecotinate sodium salt = 75 : 25 (Ila with R' = Ci 1H23 / C13H27 = 75 1 25, and M+= Na+), against the established C12C14 - 2 EO - SO4Na to find an alternative cleaning detergent with a similar wash performance that is 1 ,4-dioxane free.F) Application test in Launder-O-meter - Primary detergency240630W00124The 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 A is an example for a typical detergent formulation. Formulation B is Formulation A without the alkyl ether sulfate. Formulation C is Formulation B with the inventive surfactant mixture (I E1 ; la with R' = Ci 1 H23 / C13H27 = 751 25, and M+= Na+). Formulation D is Formulation B with the inventive surfactant mixture (IE2; Ila with R' = Ci 1 H23 / C13H27 = 75 1 25, and M+= Na+).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.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 8 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 a broad range of typical kinds of soil: lard, soybean oil, cacao, chocolate, butterfat, sebum and lipstick.Washing conditions:240630W00125Droducer: wfk-Testgewebe, Christenfeld 10, 41379 Bruggen; Swissatest Testmaterialien AG, MbvenstraBe 12, CH-9015 St. Gallen; Center for Testmaterials B.V., Stoomloggerweg 11 , NL-3133 VlaardingenTable 6 shows results of primary detergency in a launder-o-meter test at 30°C using 8 stains on fabric (CFT-C-S 10, CFT C-S 62, CFT-C-S 70, CFT C-S 78, EMPA 112, EMPA 125, EMPA 141 / 1, Wfk 20 D), 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. L*, a* and b* values of fabric before and after washing was detected and difference (in delta E) was noted. As shown in example IE1 , the formulation C with the inventive surfactant la (139.4 delta E values) removes the 8 stains better than formulation A comprising the classical detergent surfactant alkyl ether sulfate sodium salt (134.7 delta E values, comparative example CE5). Formulation B provides less stain removal (122.6 delta E values, comparative example CE7). Example IE2 shows that formulation D comprising inventive surfactant Ila (132.3 delta E values, inventive example IE2) removes the 8 stains better than formulation B but not as good as formulation A does. However, the difference is rather small. It is noted that the inventive surfactants IE1 and IE2 are free of 1 ,4- dioxane while established alkyl ether sulfate surfactants, such as C12C14-2EO-SO4Na might comprise certain amounts of 1 ,4-dioxane.Table 6: Primary detergency in a launder-o-meter test at 30°C using 8 stains (CFT-C-S 10, CFT C-S 62, CFT-C-S 70, CFT C-S 78, EMPA 112, EMPA 125, EMPA 141 / 1 , Wfk 20 D) on fabrics after 60 min with and without surfactant in hard water240630W00126G) Detergency in a fully-equipped detergent formulation including proteaseFollowing detergent formulations with enzymes 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 - SC Na (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. As protease Lavergy PRO 114 LS was used. Formulation E is an 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 (IE1; la with R' = C11H23 / C13H27 = 75 / 25, and M+= Na+).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.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 6240630W00127 stains from the monitor are summed up. The higher the value, the better the performance. The stains cover a broad range of typical kinds of soil, which are of relevance regarding protease: blood gras egg, milk, and chocolate.Washing conditions:Droducer: 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 results of detergency in presence of protease in a launder-o-meter test at 30°C using 6 stains on fabric (CFT-PC 05, EMPA 116, CFT-C-S 39, CFT-C-S 38, CFT-C-S 07, EMPA 112), 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 L*, a* and b* values 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 la (83.9 delta E values) removes the 6 stains better than formulation E comprising the classical detergent surfactant alkyl ether sulfate sodium salt (80.7 delta E values, comparative example CE5). Formulation F provides less stain removal (70.9 delta E values, comparative example CE7).Table 7: Detergency in presence of protease in a launder-o-meter test at 30°C using 6 stains (CFT-PC 05, EMPA 116, CFT-C-S 39, CFT-C-S 38, CFT-C-S 07, EMPA 112) on fabrics after 60 min with and without surfactant in hard water240630W00128H) Detergency in a fully-equipped detergent formulation including amylaseFollowing detergent formulations with enzymes 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 EC (Lutensol AO7 from BASF), and C12C14 - 2 EC - 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 Cleo) is a mixture of fatty acids with 12 to 18 carbon atoms. As amylase Lavergy A STAR was used. Formulation H is an example for a typical detergent formulation. Formulation I is Formulation H without the alkyl ether sulfate. Formulation J is Formulation I with the inventive surfactant mixture (I E1 ; la with R' = Ci 1 H23 / C13H27 = 75 1 25, and M+= Na+).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.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 3240630W00129 stains from the monitor are summed up. The higher the value, the better the performance. The stains cover a broad range of typical kinds of soil, which are of relevance regarding amylase: rice starch, tapioca starch and corn starch.Washing conditions:Droducer: 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 results of detergency in presence of amylase in a launder-o-meter test at 30°C using 3 stains on fabric (CFT-C-S 28, CFT-C-S 129, EMPA 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 J with the inventive surfactant la (87.8 delta E values) removes the 3 stains better than formulation H comprising the classical detergent surfactant alkyl ether sulfate sodium salt (82.5 delta E values, comparative example CE5). Formulation I shows a control stain removal (85.6 delta E values, comparative example CE7) wherein amylase activity is not affected by the inventive surfactant or the AES surfactant.Table 8: Detergency in presence of amylase in a launder-o-meter test at 30°C using 3 stains (CFT-C-S 28, CFT- C-S 129, EMPA 161) on fabrics after 60 min with and without surfactant in hard waterI) BiodegradabilityTable 9 shows a significant biodegradability of 61 % and 66% within 28 days under aerobic conditions using a sludge from a communal sewage plant in Germany for the inventive surfactant IE1. Test conditions according to240630W00130OECD 301 F were used as described above. The value of 61 % and 66% within 28 days fulfills the requirement of min. 60% within 28 days for a detergent surfactant.Table 9: Biodegradability within 28 days under aerobic conditions with sludge from communal sewage plant

Claims

240630W001Claims1. A compound having a structure according to Formula (1) or Formula (2)whereinR' is an aliphatic, saturated or unsaturated, linear or branched moiety comprising 8 to 17 carbon atoms, and the dotted linesI) are a moiety according to Formula (3) owhereinM+is selected from the group consisting of H+, Na+, K+, NH4+, protonated amine and protonated amino alcohol, or ii) indicate bonds to the remaining parts of the compound, wherein at least one remaining part comprises at least one six-membered ring and a directly bound moiety according to Formula (3) and optionally an -OH group.

2. The compound according to claim 1 , wherein the compound has a structure according to one formula selected from the group consisting of Formula (4) to (13):(7) (8)240630W00132M+and R' are as defined above.

3. The compound according to claim 1 or 2, wherein R' is 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.

4. The compound according to any one of claims 1 to 3, wherein M+is Na+, K+or NH4+.240630W001335. A composition, 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, formulation for emulsion polymerization, formulation for dispersions, comprising, consisting of or essentially consisting of the compound according to any of claims 1 to 4, preferably a cleaning composition and / or fabric and home care product and / or industrial and institutional cleaning product, comprising the compound according to any of claims 1 to 4.

6. The composition according to claim 5, wherein the composition is a liquid composition.

7. The composition according to claim 6, wherein the liquid compositionI) comprises Ca2+ions; and ii) comprises, by weight of the composition, from 5% to 95% of water.

8. The composition according to any one of claims 5 to 7, wherein the composition is a cleaning composition further comprisingI) 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 ill) 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, 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 polymeric240630W00134 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, antioxidants, 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.

9. The composition according to any one of claims 5 to 8, wherein said composition comprises a mixture of at least two compounds according to any of claims 1 to 4.

10. The composition according to claim 9, wherein the mixture is selected from a group consisting of(I) a mixture of compounds according to Formula (4) and (9);(II) a mixture of compounds according to Formula (5) and (10);(ill) a mixture of compounds according to Formula (6) and (11);(iv) a mixture of compounds according to Formula (7) and (12); and(v) a mixture of compounds according to Formula (8) and (13).11 . Use of the compound according to any one of claims 1 to 4 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 ink jet inks, in formulations for electro plating, in cementitious compositions, in gypsum compositions, as dispersant or wetting agent or emulsifier.

12. The use according to claim 11 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 / or240630W00135 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.

13. A cleaning method comprising contacting a cleaning composition according to any one of claims 5 to 10 with an object that requires cleaning, preferably a laundry or a hard surface household item.

14. A process to prepare the compound according to any one of claims 1 to 4 comprising reacting a compound according to Formula (14)wherein R' is an aliphatic, saturated or unsaturated, linear or branched moiety comprising 8 to 17 carbon atoms with a compound according to Formula (15) or Formula (16)wherein the dotted linesI) are a moiety according to Formula (3) as described above, orII) indicate bonds to the remaining parts of the compound, wherein at least one remaining part comprises at least one six-membered ring and a directly bound moiety according to Formula (3) and optionally an -OH group.

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