PROCESSO PARA PRODUZIR UM SAL DE ORGANOÉTER SULFATO DE UM ÉSTER DE AMINOÁCIDO ALCOXILADO, ÉSTER DE AMINOÁCIDO ALCOXILADO OU SEU SAL DE ORGANOÉTER SULFATO, USO DE PELO MENOS UM ÉSTER DE AMINOÁCIDO ALCOXILADO E / OU PELO MENOS UM SAL DE ORGANOÉTER SULFATO DE ÉSTER DE AMINOÁCIDO ALCOXILADO, COMPOSIÇÃO, E, MÉTODOS PARA PRESERVAR UMA COMPOSIÇÃO CONTRA CONTAMINAÇÃO OU CRESCIMENTO MICROBIANO E PARA LAVAR TECIDOS OU PARA LIMPAR SUPERFÍCIES DURAS

Abstract

The invention relates to a process for the preparation of organoethersulfate salts of amino acids esters from alkoxylated alcohols, the ester salts, the ester, their use and compositions comprising such ester and / or ester salt.

Description

[001] The invention relates to a process for the preparation of organoether sulfate salts of amino acid esters from alkoxylated alcohols.

[002] Organosulfate salts, such as alkyl sulfate salts and alkyl ether sulfate salts, are known to be water-soluble salts, used as detergents or wetting agents.

[003] Amino acid esters of alkoxylated alcohols and their salts are also known.

[004] Document FR2977585B1 describes a process for the synthesis of α-amino acid esters of C7 to C36 alcohols from the amino acid or its salt in the presence of an acid catalyst, such as sulfuric acid, in the presence of water, starting from amino acids or their salts.

[005] Document WO2015172158 describes alpha ethanesulfonic acid salts and higher amino acid esters.==-0

[006] Document WO2011002746 describes the preparation of amino acid esters with sulfuric acid.

[007] TRIVEDI, TJ et al. ChemSusChem 2011, number 4, pages Pages 604-608 describe a synthetic pathway for alpha-C3-C4 amino acid ester salts and lauryl sulfate that includes the formation of an amino acid ester as a hydrochloride salt, followed by ion exchange with sodium lauryl sulfate.

[008] Document SU1276661 describes salts of protonated amino acid esters and anionic alkyl sulfates. They are obtained from Petition 870250084807, dated 09 / 19 / 2025, p. 112 / 168 / 50 of amino acids with 2 moles of hexadecanol and excess sulfuric acid in dioxane.

[009] Documents JP49076822 and JP51036735 describe a process for the preparation of amino acid ester salts with alkyl sulfates by heating 1 mol of amino acid with at least 3 mols of lauryl alcohol in the presence of sulfuric acid. The synthesis is carried out in toluene as solvent.

[0010] Currently available methods for the synthesis of organosulfate salts of amino acid esters, using amino acids as starting materials, are carried out in organic solvents and often involve an anion exchange after the synthesis of the amino acid ester to replace the anion present in the esterification reaction with an organosulfate.

[0011] Similarly, WO 2019 / 007750 describes steramines from amino acid alkoxylated monoalcohols, which lists, among others, sulfuric acid as an acid for the synthesis. However, alkyl ether sulfates are not obtained as counterions. The molar ratio between amino acids and hydroxyl groups of the alkoxylated alcohol in step a) of the described process is from 0.8:1 to 1:1.5. In one embodiment, the process is carried out with the molar ratio of the acid to the hydroxyl groups of the alkoxylated alcohol in step a) in the range of 0.1:1 to 1:1.

[0012] Document EP0847987 describes a process in which esters of amino acids (or lactams) with linear, branched, or cyclic C2-C40 alcohols are obtained with sulfuric acid or phosphoric acid. Possible counterions are hydrogen sulfate or alkyl sulfate. No information is given on the C2-C40 ratio to sulfuric acid and amino acid, other than a minimum of 1:1:1. The process was carried out in the presence of solvents or without solvent. No alkoxylated alcohol is described as a reagent.

[0013] There is a continuing need for an improved process. Petition 870250084807, dated 19 / 09 / 2025, p. 113 / 168 / 50 for the preparation of organoether sulfate salts of alkoxylated amino acid esters with high yield and fast reaction times, without handling organic solvents and without handling corrosive gaseous acids. There is also a need for a process for the preparation of organoether sulfate and alkoxylated amino acid esters in a single reaction with high yield, reduced reaction time and reduced synthesis complexity. There is also a need for a process that allows the quantitative reaction of amino acids and amino acid precursors, such as lactams, with alcohols that have low solubility in water and therefore can only be dispersed in water to obtain organoether sulfate salts of amino acid esters.All these processes should preferably use a reduced amount of organic solvents, as these need to be removed before they can be used in cleaning compositions, especially in compositions for domestic use.

[0014] Therefore, there is a continuing need to provide alkoxylated amino acid ester salts and, therefore, to use them by combining an alkoxylated amino acid ester active with an organoether sulfate detergent for incorporation into enhanced detergent formulations, especially for textile and household care applications such as hard surface cleaning.

[0015] One of the objectives of the present invention was to provide a process that would meet the objectives and needs identified above.

[0016] This objective has been achieved by the present invention, as described below and reflected in the claims and examples. Definitions

[0017] Throughout this descriptive report and the claims that follow, unless the context requires otherwise, the word “comprise” and variations such as “comprises” and “comprising” will be understood as implying the inclusion of a whole number or step or group of numbers. Petition 870250084807, dated 09 / 19 / 2025, page 114 / 168 / 50 whole numbers or steps declared, but not the exclusion of any other whole number or step or group of whole numbers or steps. When used in this document, the term “comprising” may be replaced by the term “containing” or “including” or, sometimes, when used in this document, by the term “having”.

[0018] When used in this document, “consisting of” excludes any element, step, or ingredient not specified in the claim element. When used in this document, “essentially consisting of” does not exclude materials or steps that do not materially affect the basic and novel characteristics of the claim.

[0019] In each instance in this document, either of the terms “comprising”, “essentially consisting of” and “consisting of” may be replaced by either of the other two terms. “Comprising” may be replaced in a preferred embodiment by “essentially consisting of” and both may be replaced by “consisting of” in a still more preferred embodiment.

[0020] The compositions of the present description may “comprise” (i.e., contain other ingredients), “consist essentially of” (comprise mainly or almost exclusively the ingredients mentioned and other ingredients only in very small quantities, mainly only as impurities), or “consist of” (i.e., contain only the ingredients mentioned and, in addition, may contain only impurities that cannot be avoided in a technical environment, preferably only the ingredients) components of the present description.

[0021] Similarly, the terms “substantially free of...” or “substantially exempt from.” or “(containing / comprising) essentially none.” may be used in this document; this means that the indicated material is not, at a minimum, deliberately added to the composition to form part of it, or, preferably, is not present in Petition 870250084807, dated 19 / 09 / 2025, p. 115 / 168 / 50 analytically detectable levels. The intention is to include compositions in which the indicated material is present only as an impurity in one of the other deliberately included materials. The indicated material may be present, if present, at a level of less than 1%, or even less than 0.1%, or even further less than 0.01%, or even 0%, by weight of the composition.

[0022] Generally, as used herein, the term “obtainable by” means that the corresponding products do not necessarily need to be produced (i.e., obtained) by the corresponding method or process described in the respective specific context, but also include composite products that exhibit all the characteristics of a product produced (obtained) by said corresponding method or process, wherein said products were not actually produced (obtained) by such method or process. However, the term “obtainable by” also includes the more limiting term “obtained by”, i.e., products that were actually produced (obtained) by a method or process described in the respective specific context.

[0023] When used herein, any definition requiring that a compound or a substituent of a compound consist of “at least a number of carbon atoms”, number of carbon atoms refers to the total number of carbon atoms in said compound or substituent of a compound. For example, for a substituent described as “alkyl ether with at least 8 carbon atoms comprising alkylene oxide groups”, the total number of at least 8 carbon atoms must be the sum of the number of carbon atoms of the alkyl moiety and the number of carbon atoms of the alkylene oxide moieties.

[0024] All these terms not specifically defined have their common meaning, as known in the field of organic chemistry.

[0025] The term “containing a hydroxyl group” means that only one -OH group is present. Any functionalized group derived from a Petition 870250084807, dated 09 / 19 / 2025, p. 116 / 168 / 50 hydroxyl group, as an ether group, is not considered an -OH group.

[0026] As used herein, the articles “a” and “an,” when used in a claim or embodiment, are understood to mean one or more of what is claimed or described. As used herein, the terms “include” and “including” are intended to be non-limiting and therefore encompass more than the specific item mentioned after those words.

[0027] The term “about”, as used herein, covers the exact number “X” mentioned as, for example, “about X%”, etc., and small variations of X, including from minus 5 to plus 5% deviation from X (with X for this calculation defined as 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 given value X is already “100%” (as for purity, etc.), then the term “about” clearly can and therefore does mean only deviations from it that are less than “100”.

[0028] The term “water-free” means that the composition contains no more than 5% by weight of water based on the total amount of solvent; in another embodiment, no more than 1% by weight of water based on the total amount of solvent; in another embodiment, the solvent contains no water at all.

[0029] All temperatures herein are in degrees Celsius (°C), unless otherwise indicated. Unless otherwise specified, all measurements herein are taken at 20°C and under atmospheric pressure. In all embodiments of the present description, all percentages are by weight of the total composition, unless specifically indicated otherwise. All ratios are by weight, unless specifically indicated otherwise.

[0030] The phrase “composition for tissue treatment” is intended to include compositions and formulations intended for tissue treatment. Such Petition 870250084807, dated 09 / 19 / 2025, pp. 117 / 168 / 50 compositions include, but are not limited to, compositions and detergents for cleaning clothes, fabric softening compositions, fabric improving compositions, fabric refreshing compositions, laundry pre-wash, laundry pre-treatment, laundry washing additives, spray products, dry cleaning agent or composition, laundry rinsing additive, washing additive, post-rinse fabric treatment, ironing aid, unit dose formulation, delayed dispensing formulation, detergent contained in or on a porous substrate or nonwoven sheet, and other suitable forms that may be evident to one skilled in the art in view of the teachings herein and detailed below in describing the compositions.Such compositions can be used as a pre-wash treatment, a post-wash treatment, or can be added during the rinse or wash cycle of the washing operation, as detailed below when describing the use and application of the invention and compositions comprising such steramine and its salts.

[0031] The term “containing a hydroxy group” means that only one -OH group is present. Any functionalized group derived from a hydroxy group, such as an ether group, is not considered an -OH group.

[0032] Throughout this description, the term “compound of the invention” may be used instead of “steramine(s) of the invention and / or its salt(s)” and “steramine(s) and / or its salt(s) of this (present) invention”, meaning those compounds described herein as the invention, defined by their structure and / or their production or obtaining process by the process defined herein. Similarly, “process of the invention” means the process described and defined in this document.

[0033] Preferably, “compound of the invention” means the organoether sulfate salts of amino acid esters, as defined in this document, by their production process and their resulting structures from such process. Petition 870250084807, dated 09 / 19 / 2025, page 118 / 168 / 50 Detailed description

[0034] The definitions and their preferences provided in the “Definition” section above are included as part of this invention, as described below.

[0035] The specific embodiments described throughout this description are covered by the present invention as part of this invention; the various additional options being described in this descriptive report as “optional”, “preferred”, “more preferred”, “even more preferred” or “much more preferred” options (or “preferably”, etc.) of a specific embodiment may be individually and independently selected (unless such independent selection is not possible by virtue of the nature of that embodiment or if such independent selection is explicitly excluded) and then combined within any of the other embodiments (where other options and preferences may also be individually and independently selected, unless such independent selection is not possible by virtue of the nature of that embodiment or if such independent selection is explicitly excluded), with each and all of these possible combinations being included as part of this invention as individual embodiments. Process

[0036] The present invention relates to a process for the synthesis of organoether sulfate salts of alkoxylated amino acid esters from monoalcohols and alpha-amino acids alkoxylated with the alkyl ether sulfate counterion.

[0037] The compounds of the invention can be obtained from the reaction of at least 2 moles of alkoxylated monoalcohols with 1 mole of alpha-amino acid and 1 mole of sulfuric acid in the presence of water.

[0038] The general structure of the compounds of the invention is shown in formula (I) below. Petition 870250084807, dated 09 / 19 / 2025, p. 119 / 168 / 50 (Formula (I)) with n = 1 - 200 R = C1-C36-alkyl or -alkenyl or -phenyl or -alkylphenyl R1, R2 = hydrogen or C1-C12-alkyl or -phenyl R3, R4, R5, R6 = hydrogen or C1 - C20-alkyl

[0039] Therefore, the present invention relates to a process for the synthesis of organoether sulfate salts of alkoxylated amino acid esters, comprising the steps of (i) reacting at least one alpha-amino acid and at least one alkoxylated alcohol with sulfuric acid in aqueous solution; and (ii) optionally removing water and / or removing excess alcohol.

[0040] More specifically, the present invention relates to a process for producing organoether sulfate salts of alkoxylated amino acid esters, comprising the steps of (A) providing at least one alcohol containing a hydroxy group, wherein such hydroxy group is alkoxylated with at least one alkylene oxide fraction, preferably from at least 1 to 200, more preferably from 1 to 100, more preferably up to 50, even more preferably up to 20, even more preferably up to 20, even more preferably up to 15 and, most preferably, up to 10 moles of alkylene oxide per hydroxy group, (B) providing at least one alpha-amino acid, and (C) sulfuric acid, wherein the molar ratios are at least as follows: - the ratio between amino acids and hydroxyl groups of the alkoxylated alcohol is at least 1:2 or 1:(greater than 2); and Petition 870250084807, dated 09 / 19 / 2025, pp. 120 / 168 / 50 - the ratio of sulfuric acid to amino acid is 0.9:1 to 1.1:1 and - the ratio between the hydroxyl groups of the alkoxylated alcohol and sulfuric acid is at least 2:1 and preferably (>2):1; - the molar ratio of water to amino acid is from 0.5:1 to 10:1, preferably up to 5:1, more preferably up to 2:1, and much more preferably up to 1:1, such as approximately 1:1 and exactly 1:1; (D) react at least one alkoxylated alcohol with at least one alpha-amino acid in the presence of sulfuric acid to obtain the organoether sulfate salts of alkoxylated amino acid esters, (E) optionally remove water and / or excess alcohol during and optionally also after the reaction to obtain the organoether sulfate salts of alkoxylated amino acid esters.

[0041] Other steps of the process may be included in the invention process: The reaction mixture can be inertized before and / or during the reaction, preferably before the addition of sulfuric acid.

[0042] Inerting can be achieved by means of gas vapor, such as nitrogen or argon, and / or by the addition of an oxygen-scavenging compound.

[0043] Such oxygen scavengers are known. It is advantageous to use small amounts of hypophosphorous compound, such as hypophosphorous acid or any of its salts, especially any alkaline, ammonium or alkaline earth salts, more preferably the acid, which can be added to the reaction mixture before the addition of sulfuric acid.

[0044] As one of the effects, this addition of the oxygen-scavenging compound leads to a better coloration of the resulting product, that is, to a reduced coloration, compared to the omission of this addition.

[0045] The reaction is carried out - at a temperature of 50 to 200°C, preferably 100 to Petition 870250084807, dated 09 / 19 / 2025, pp. 121 / 168 / 50 200°C, more preferably from 120°C to 180°C, more preferably from 120°C to 150°C, such as 60, 70, 80, 90, 110, 115, 120, 125, 130, 135, 140, 145, 160, 170, 190°C; - for a period of 1 to 30, preferably 2, more preferably 3 hours, and preferably up to 20, more preferably up to 165, even more preferably up to 10 hours, as preferably from 3 to 24, more preferably from 5 to 24, much more preferably from 10 to 24 hour(s); and - at a pressure of 0.1 to 1000 kPa (0.001 to 10 bar), such as 10 (0.1), more preferably 100 (1), and preferably up to 800 (8), more preferably up to 500 (5), even more preferably up to 400 kPa (4 bar), such as 100 to 1000 (1 to 10), more preferably 100 to 500 (1 to 5), even more preferably 100 to 400 kPa (1 to 4 bar).

[0046] Preferably, temperature, duration and pressure are all defined individually beforehand, preferably the preferred ranges of all three parameters are selected, more preferably the most preferred ranges of all three parameters and so on.

[0047] In one embodiment of the present invention, the temperature is kept constant throughout the reaction. In another embodiment, the temperature is varied within the temperature range during the reaction.

[0048] In one embodiment of the present invention, the reaction with sulfuric acid is carried out under atmospheric pressure. In another embodiment, the reaction with sulfuric acid is carried out in a closed container under a pressure of 0.1 to 100 kPa (0.001 to 1 bar). In yet another embodiment, the reaction with sulfuric acid is carried out in a closed container under a pressure of more than 100 to 1000 kPa (1 to 10 bar).

[0049] In one embodiment, a protective atmosphere of an inert gas, such as gaseous nitrogen or argon, is used to carry out the reaction.

[0050] In another method, inertization is carried out by adding Petition 870250084807, dated 09 / 19 / 2025, page 122 / 168 / 50 an oxygen scavenging agent, preferably a hypophosphorous compound, more preferably hypophosphorous acid.

[0051] In another embodiment, inerting is carried out by adding an oxygen-scavenging agent, as defined above, and using a protective atmosphere of an inert gas, as defined above.

[0052] It is evident that temperature, pressure, and duration can be chosen independently of the values ​​and ranges described and combined with each other. Similarly, the way in which inerting is achieved can also be chosen and combined with the temperatures, durations, and pressures chosen, all as defined previously.

[0053] During or after the reaction, preferably at least during the reaction, water and / or excess alcohol can be removed. The removal of water and alcohol can be carried out by all techniques known in the art, for example, by applying a gas stream and / or by applying a distillation method, preferably a distillation, more preferably a distillation method under reduced pressure and / or high temperature, preferably both, a preferred method being the use of an apparatus such as a Dean-Stark trap.

[0054] In another embodiment, water and / or alcohol are removed by means of a gas stream, such as an inert gas like nitrogen or argon, preferably nitrogen, or water vapor, preferably using an inert gas, more preferably nitrogen.

[0055] In a more preferred embodiment, water and / or alcohol are removed by applying vacuum and / or increasing the temperature, preferably using an apparatus such as a Dean-Stark trap.

[0056] Optional removal of water and / or excess alcohol is carried out, most preferably, by applying vacuum in the range of 0.01 kPa to 80 kPa (0.1 mbar to 800 mbar), preferably from 0.1 kPa to 50 kPa (1 mbar to Petition 870250084807, dated 09 / 19 / 2025, pp. 123 / 168 / 50 500 mbar) and, more preferably, from 1 kPa to 10 kPa (10 mbar to 100 mbar), and using high temperatures.

[0057] In a preferred embodiment, during the reaction, a vapor of inert gas, such as nitrogen or argon, preferably nitrogen, is passed through the reaction mixture. This helps to keep the reaction mixture inert, but also assists in removing water of formation from the chemical reaction and thus in controlling the amount of water present.

[0058] The reaction is carried out from a suspension of the typically solid amino acid(s) in alkoxylated alcohol(s). Typically, no organic solvent is added or present initially, other than the alkoxylated alcohol(s) and water. During the course of the reaction, the product formed is soluble and therefore the reaction mixture tends to become a solution, typically resulting in a homogeneous solution of the compound(s) of the invention in alkoxylated alcohol containing residual amounts of water — the content of alkoxylated alcohol and water depending on whether and how the measurement of the removal process of such alcohols and / or water, as defined elsewhere in this document, is carried out.

[0059] These “residual quantities of water” may be less than 5 percent, preferably less than 2 and — typically and therefore even more preferably — less than 1 percent based on the total weight of the reaction mixture.

[0060] The sulfuric acid used typically contains some water. In one embodiment, the sulfuric acid is used as concentrated sulfuric acid. In another embodiment, the sulfuric acid is used as a 96 to 98% by weight solution of sulfuric acid in water. In a further embodiment, the sulfuric acid is used as an 80% by weight solution of sulfuric acid in water.

[0061] In one embodiment, no other water is introduced into the reaction, besides the water introduced into the sulfuric acid, the amino acid(s) and Petition 870250084807, dated 09 / 19 / 2025, p. 124 / 168 / 50 in alcoxylated alcohol(s).

[0062] In a preferred embodiment, the amount of water (present at the beginning of the reaction) per mole of amino acid is from 0.1:1 to 10:1, preferably up to 5:1, more preferably up to 2:1 and, much more preferably, up to 1:1, and preferably from 0.5:1; most preferably from 0.7:1, as about 1:1 and exactly 1:1.

[0063] Preferably, no other organic solvent is introduced into the reaction, apart from the organic solvents possibly present in any of the starting materials used, namely, sulfuric acid, amino acid(s) and alkoxylated alcohol(s).

[0064] In one embodiment, the amino acid, the alkoxylated alcohol, water, and the optional oxygen scavenger are mixed in a solution or emulsion, preferably a solution. Such a solution is obtained when all ingredients are soluble. The amount of water may be adjusted to improve dissolution, the amount of water being within the ranges defined elsewhere in this document.

[0065] The typical amino acid concentration in the reaction mixture is in the range of 1% by weight to 99%, preferably 5 to 50%, more preferably 5 to 30%, even more preferably 10 to 25% by weight, based on the total weight of amino acid, alkoxylated alcohol and water. The amount also depends, of course, on the relative molecular weights of the reagents; the higher the molecular weight, for example, of the alkoxylated alcohol, the lower the relative amount of amino acid normally chosen, to compensate, for example, for viscosity effects.

[0066] Preferably, the alkoxylated alcohol(s) serve(s) as the solvent for the reaction, the amounts of water being introduced or present in the reaction mixture at the start of the reaction as defined elsewhere in this document.

[0067] In one embodiment of the present invention, the total quantity Petition 870250084807, dated 09 / 19 / 2025, p. 125 / 168 / 50 of sulfuric acid is added at the beginning of the reaction to at least one amino acid and to the alkoxylated alcohol. In another embodiment, sulfuric acid is added dropwise over a period of 0.1 to 15 hours, preferably up to 10 hours, more preferably up to 5 hours, to the reaction mixture comprising at least one alkoxylated alcohol and at least one amino acid. Typically, the duration of the sulfuric acid addition is no longer than 5 hours, preferably no longer than 3 hours, and even more preferably no longer than 2 hours, but can be up to 60, 45, 30 or even 15 minutes.

[0068] In another preferred embodiment, the duration of the addition of sulfuric acid is at most 10% of the total reaction time, more preferably at most 5%.

[0069] It is clear that the time of addition of sulfuric acid also depends, in typically known ways, on the scale of the reaction and its total duration.

[0070] In another embodiment, sulfuric acid is added to the mixture of alkoxylated alcohol(s), amino acid(s) and, optionally, water. The reaction mixture may be at an elevated temperature or at room temperature when the addition of sulfuric acid is initiated. During this addition, the temperature of the reaction mixture may increase due to the release of energy from the chemical reaction. During or after the addition of sulfuric acid, the temperature of the reaction mixture may be raised to the reaction temperatures defined elsewhere in this document, preferably after.

[0071] The reaction compartment is typically - and preferably - equipped with a condenser to control reflux.

[0072] Backflow can also be controlled by increasing the pressure within the reaction compartment by selecting appropriate temperatures and corresponding pressures within the ranges defined elsewhere in this document.

[0073] In one embodiment of the present invention, the reaction is carried out Petition 870250084807, dated 09 / 19 / 2025, page 126 / 168 / 50 mixing at least one alkoxylated alcohol and at least one amino acid and water to obtain an aqueous solution or aqueous suspension, optionally adding at least one oxygen scavenging agent, as defined above, and / or inertizing, preferably by applying an inert gas, such as providing this gas preferably by bubbling it through the reaction mixture, then adding sulfuric acid, optionally followed by sealing the reaction vessel and, optionally, applying pressure, as defined elsewhere in this document, heating the mixture to a temperature as detailed elsewhere in this document, reacting for a period as detailed elsewhere in this document and at a pressure as detailed elsewhere in this document, thus reacting the mixture to obtain the alkoxylated steramine sulfate salts, as defined in this invention.

[0074] Organoether sulfates are esters derived from alcohols and sulfuric acid. Organoether sulfates comprise the “RO-SO3-” group, comprising a “-O-SO3” core and an R group that can be selected from the group consisting of linear alkyl, branched alkyl, linear alkyl ether, branched alkyl ether and phenoxyalkyl.

[0075] Alcohols containing a hydroxyl group are well known in the art. The alcohol may contain linear, branched and / or cyclic alkyl fragments. In addition, the alcohol may also contain aromatic fragments, as well as combinations of alkyl and aromatic fragments ("aralkyl" fragments). Furthermore, the alcohol may also contain alkyl ether fragments.

[0076] The alkoxylated alcohol (A) for the alkoxylated amino acid esters and their salt is an alcohol containing a hydroxyl group that can react during the process of the invention. The alkoxylated alcohol, however, can be derived from alcohols with more than one hydroxyl group, provided that such higher alcohols are alkoxylated and modified in such a way that only one group Petition 870250084807, dated 09 / 19 / 2025, page 127 / 168 / 50 hydroxyl group per alkoxylated alcohol compound remain free for reaction in the invention process. This can be done, for example, by modification (often also referred to as “chain terminal blocking”) of any other hydroxyl group present to produce an alkoxylated monoalcohol with only one hydroxyl group present before the present reaction is carried out.

[0077] The alkoxylated monoalcohol is preferably selected from among alkoxylated monoalcohols, such as C1 to C36 alkanols, selected from the group comprising C2 to C36 linear alcohols, such as mixtures of these alcohols selected from C6 to C22 fatty alcohols, preferably C8 to C22 fatty alcohols, more preferably C12 and C14 fatty alcohols, more preferably C16 and C18 fatty alcohols; C3 to C36 branched alcohols, such as 2-ethylhexanol, 2-propylheptanol, isotridecanol, isononanol, C9-C17 oxoalcohols; C3 to C36 alkoxylated branched alcohols, such as alkoxylated 2-ethylhexanol, alkoxylated 2-propylheptanol, alkoxylated isotridecanol, alkoxylated isononanol, C9 to C17 alkoxylated oxoalcohols; and alkoxylated phenoxyalkanols, such as alkoxylated phenoxyethanol; with alcohols preferably selected from the group of C2 to C22 linear alkoxylated monoalcohols, more preferably a C12 to C14 linear alkoxylated monoalcohol and / or alkoxylated 2-propyl-heptanol; with the alkoxylation and any chain-terminal blocking of other hydroxyl groups optionally being present beforehand — so that, in fact, the alkoxylated alcohol contains only one hydroxyl group, although the alcohol or the alkoxylated alcohol may have contained two or more hydroxyl groups before the chain-terminal blocking of all but one hydroxyl groups — to be carried out using standard means and prior to the process of the invention.

[0078] Obviously, such alcohols are known, many of them from natural sources. Others can be produced from natural sources, Petition 870250084807, dated 09 / 19 / 2025, pp. 128 / 168 / 50 modifying them. If such modification results in the addition of carbon atoms, for example, by chemical addition reactions, and if such addition reactions use non-fossil carbon atoms, then the alcohols contain only non-fossil carbon. Therefore, it is preferable that only naturally occurring alcohols and / or alcohols derived from nature (not produced by adding non-fossil carbon in building blocks to obtain such naturally derived alcohols) be used in this invention. Even more preferably, only naturally occurring alcohols are used.

[0079] The alcohol (A) used for the alkoxylated amino acid esters and salt thereof produced according to the process of the invention is an alkoxylated alcohol that is obtained by alkoxylation of the hydroxy group of the alcohol with one or more alkylene oxides to produce alkylene oxy chains having a free hydroxy group at the end, such chains comprising one or more fractions derived from alkylene oxides selected from C2 to C22 alkylene oxides, preferably C2-C4 alkylene oxides, while the fractions derived from the alkylene oxide(s) may be arranged in random order, in block or multiblock or combinations thereof, preferably as a block.

[0080] The alkoxylation of alcohols can be achieved by carrying out the alkoxylation reaction with only one alkylene oxide or with more than one alkylene oxide. If more than one alkylene oxide is used, the resulting alkyl ether alcohols comprise alkylene oxide units randomly distributed, or a block of one alkylene oxide followed by a block of another alkylene oxide, or a block of one alkylene oxide followed by another block comprising two or more alkylene oxides arranged in random order, or a block comprising two or more alkylene oxides followed by another block comprising two or more alkylene oxides, each of these blocks differing in its relative quantity of alkylene oxides, in its arrangement of oxides of Petition 870250084807, dated 09 / 19 / 2025, p. 129 / 168 / 50 alkylene and / or in the identity of alkylene oxides, such that the two blocks linked together differ in their chemical composition and / or arrangement; any combination of arrangements is, in principle, possible and, as such, covered by the present invention.

[0081] In one embodiment of the present invention, alkoxylated alkyl alcohols with only a single alkylene oxide are used. In another embodiment, alkoxylated alkyl alcohols with a first alkylene oxide followed by alkoxylation with a second alkylene oxide are used, thus forming a block structure with different alkylene oxide blocks.

[0082] It is evident that, when alternating between blocks, there may be — depending on how the alkoxylation reaction is carried out — a relatively small “region” between the blocks, without a sharp “edge” between them, identical in all molecules of the alkoxylated monoalcohol, so that there may be some “dirty” structures, meaning that very small amounts (such as one or perhaps two or three) of alkylene oxides of the first type used may be inserted only after one or more of the second alkylene oxides have reacted; this depends mainly on the conversion rate achieved in the first alkylation reaction at the time the second alkylene oxide is added, i.e., whether, at the time of the addition of the second alkylene oxide, there are still some unreacted amounts of the first alkylene oxide.

[0083] Similarly, it is evident that, due to the statistical reaction of alkoxylation polymerization, the block lengths may differ slightly from one compound to another, and therefore, the “alkoxylated monoalcohol” is actually a mixture of compounds with slightly different chain lengths and block lengths.

[0084] Furthermore, it is evident to one skilled in the art that the definition of the compounds of the invention, according to the formula(s) herein Petition 870250084807, dated 09 / 19 / 2025, page(s) 130 / 168 / 50 presented, is a theoretical result of an optimized way of carrying out the respective reaction and process, in which all functional groups (of the respective starting material or any intermediate) have undergone a complete reaction. However, it is also clear that a complete reaction (100% degree of conversion) is an idealized assumption. In reality, the degree of conversion is usually less than 100%. Unreacted hydroxyl groups, etc., may be present. This fact is known to one skilled in the art for such reactions, as well as for the structure according to the formulas. Regardless, the reaction for obtaining said structure is described in the description above.Following the general reaction conditions, as well as the specific reaction conditions detailed herein, including the examples section, the actual structure for each individual reaction case / condition is obvious to one skilled in the art or can be determined using standard methods.

[0085] For completeness purposes, it is mentioned in connection with the present invention, especially in connection with the steramines according to the formula described herein and, furthermore, with the alkoxylation reactions leading to the alkoxylated alcohols used for the present reaction, that the reactions used and, especially, the alkoxylation reaction with the alkoxylated alcohols are known to a skilled person as leading to statistical distributions.This means that when, for example, “20 units of ethylene oxide (“20 EO”) per functional group of the molecule (i.e., hereafter for simplicity referred to as the “core”) to be reacted” are used, this does not necessarily mean that each functional group of the core will actually bear exactly 20 EO units; rather, the resulting product obtained from such a reaction is a mixture of several slightly different products, with the main product contained in the process product being the core product being modified in each functional group with exactly 20 EO units per functional group; however, due to statistical reasons, Petition 870250084807, dated 19 / 09 / 2025, p. 131 / 168 / 50 this “main product” (in the present case the “alkoxylated monoalcohol”) is accompanied by many products having small variations of this main product, where for example the same central molecule is modified with EO, but the lengths of the EO chains per functional group differ slightly from 20: some chains are slightly longer and others slightly shorter, a typically even smaller quantity containing even more EO and some even less EO, a still smaller quantity differs in greater extent etc.

[0086] The more functional groups the nucleus can contain (for example, the more hydroxyl groups an alcohol contains) and the more alkylene oxide units per functional group are used, the greater the overall deviation from the “target” molecule represented by such formulas: this means that the content of the target molecule (represented in the formula(s) described here) decreases in the resulting product mixture (i.e., such content then falls below 100% of the total amount of the compound obtained), and more different and subtle variations of the target molecule are present, in addition to the target molecule.

[0087] However, this does not cause any problem, since the explanation here for such reactions is the same “problem” observed for each polymerization reaction: Each polymer in preparation is defined by a chemical structure. Representing such a polymeric structure, however, is as difficult as for the structures contemplated in the present invention: the more precise the definition of a polymer's structure, the more incorrect the represented structure will be. Therefore, polymers are described by the monomers from which they are created, by the reaction used (for example, “by radical polymerization”, which then implies how the monomeric units are linked) and by certain other typical values, such as the molecular weight Mw, Mn, the polydispersity index (i.e., the amplitude of the molecular weight distribution) etc. — which, in fact, is nothing more than stating that the Petition 870250084807, dated 09 / 19 / 2025, p. 132 / 168 / 50 The polymeric product obtained from the polymeric reaction is a mixture of several polymeric molecules with different chain lengths, slightly different orders of monomeric units within a chain (if more than one monomer is used), slightly different amounts of each monomeric unit within a chain (if more than one monomeric unit is used), and so on.

[0088] For the present structure contemplated in the present invention, the same difficulty explained for the description of a polymeric molecule may arise, but complicated by the fact that a defined organic molecule(s) is / are also used: the molecule(s) is / are a clearly defined chemical “organic structure(s)”, which can be defined with precision. However, the modifications through the reaction of the invention here are introduced by addition reactions with generally incomplete conversion, thus introducing the concept which is the same for the description of polymers (and their “relative description” through starting materials, i.e., monomers) in an apparently clearly defined organic molecule — by formula.

[0089] This means that, for the structure currently contemplated, although it appears to be a clearly defined structure of a “typical organic molecule”, this is not necessarily the case: the actual structure is a combination of a clearly defined organic chemical structure, fused with “polymeric descriptions” of the alkoxylated parts (when an alkoxylated alcohol is used; such parts are oligomers or polymers — depending on the number of monomeric units used for alkoxylation) and also depending on how complete the various esterifications occur.

[0090] This should be taken into account when defining the current structure: the “organic structural parts” (the structural part of amino acids) can be easily and clearly defined in terms of organic chemistry, while the “polymeric structural parts” (i.e., the alkoxylated parts and Petition 870250084807, dated 09 / 19 / 2025, page 133 / 168 / 50 the structures formed by esterification) seem — on paper — to also follow the “description of the organic chemical structure”, but, in fact, they must also be viewed from the perspective of a polymer chemist.

[0091] With this in mind, it is clear that the “structure of a formula (X)” is a combination of the organic chemistry description for the starting materials used and a polymer chemistry description for the alkoxylated parts and chains resulting from the esterification reactions and therefore the “target molecule” of the reaction, but not a “100% structure” as in other organic molecules: The structure shown is the “main component” of the process described, the product containing smaller amounts of many small variations of this main component side by side, as explained earlier.

[0092] In the context of the present invention, it is also preferable that, if compound (A) comprises an alkoxylated alcohol, the alkoxylated fragment is based on at least one C2-C22 alkylene oxide, preferably C2-C4 alkylene oxides, more preferably ethylene oxide and / or propylene oxide, the respective alcohol comprises at least one block based on ethylene oxide and / or propylene oxide, and even more preferably contains only one block consisting of ethylene oxide or consisting of two blocks, the first block — preferably the “inner block” directly linked to the hydroxy group of the alcohol — being ethylene oxide and a second block — preferably the “outer block” linked to the ethylene oxide block — being propylene oxide. More preferably, the EO block comprises at least 2 EO-derived moieties and the PO block comprises at least 2 PO-derived moieties; total quantities, preferred quantities, etc.For AO, the rules apply as defined previously.

[0093] Note that the alkylene oxide used to prepare the alkoxylated alcohol(s) may be derived from a fossil carbon source or Petition 870250084807, dated 19 / 09 / 2025, p. 134 / 168 / 50 non-fossil or even a mixture thereof. Preferably, the amount of non-fossil carbon atoms in the alkylene oxide used is at least 10%, at least 20%, at least 40%, at least 70%, at least 95%, and most preferably up to 100% based on carbon atoms derived from non-fossil sources; the same applies to the compound of the total invention as such. The skilled person is well aware of commercial alkylene oxide products made from non-fossil carbon sources (these products are often sold as “sustainable”, “renewable” or “bio-based”). For example, Croda International, Snaith, UK, sells ethylene oxide and related bioethanol-based products as “ECO”-Range. Furthermore, methods for preparing bio-based propylene oxide are also known (see Abraham, DS)., “Production of propylene oxide from propylene glycol”, Master's thesis, University of Missouri-Columbia (2007) (75 pages)).

[0094] The amino acid can, in principle, be any known amino acid. Preferably, at least one amino acid is selected from any alpha-amino acid, such as alanine, glycine, leucine, isoleucine, valine, proline, phenylalanine, arginine, asparagine, aspartic acid, aspartate, glutamine, glutamate, histidine, lysine, threonine, tryptophan, tyrosine, cysteine, methionine, serine; alpha-amino acids with secondary or tertiary amino groups, such as sarcosine, N,N-dimethylglycine; preferably alanine, valine, glycine, leucine, isoleucine, phenylalanine, more preferably alanine, valine, leucine, much more preferably alanine and valine.

[0095] Obviously, such amino acids are known, generally from natural sources. Others can be produced from natural sources by modifying them to obtain amino acids as starting material in the present invention. If such modification results in the addition of carbon atoms, for example, by chemical addition reactions, and if such addition reactions use Petition 870250084807, dated 09 / 19 / 2025, pp. 135 / 168 / 50 non-fossil carbon atoms, so amino acids contain only non-fossil carbon. Therefore, it is preferable that only naturally occurring amino acids and / or amino acids derived from nature (not produced by adding non-fossil carbon in building blocks to obtain such naturally derived amino acids) be used in this invention. Even more preferably, only naturally occurring amino acids are used.

[0096] When the salts of the amino esters of the invention are neutralized by known means, it is clear that neutral amino acid esters can also be obtained from the present process of the invention.

[0097] The present invention can also provide amino acid esters of the invention and their salts from natural amino acids and / or natural alcohols, thus enabling the supply of products with a high content of bioderived material. As the alkylene oxide(s) can also be derived from non-fossil sources, the compound of the invention can be obtained containing only carbon atoms from non-fossil sources. Such products are highly sought after by consumers and industries. Uses

[0098] The alkoxylated amino acid esters of the invention and, especially, the organoether sulfate salts, as obtained directly by the process of the invention (without subsequent desalting to obtain the neutralized amino acid esters), can be advantageously used in cleaning compositions.

[0099] They may be used as at least one amino acid ester, at least one organoether sulfate salt of at least one amino acid ester, or any combination thereof.

[00100] Therefore, another object of the present invention is the use of the alkoxylated amino acid esters mentioned above and / or their salts in cleaning compositions, specifically as prepared by the process defined herein. Petition 870250084807, dated 09 / 19 / 2025, pages 136 / 168 / 50

[00101] Alkoxylated amino acid esters and / or their salts may be added to cleaning compositions.

[00102] Alkoxylated amino acid esters and / or their salts are generally present in said formulations at a concentration of about 0.1% to about 50%, preferably about 0.25% to 15%, more preferably about 0.5% to about 10%, and even more preferably about 0.5% to about 5%, and much more preferably in amounts up to 3%, each in % by weight relative to the total weight of such composition / product, optionally further comprising about 1% to about 70% by weight of a surfactant system, wherein — specifically — for a liquid dishwashing detergent cleaning composition for hand washing or spray, such composition comprising 0.1% to 50%, preferably 1% to 35%, more preferably 3% to 30%, by weight of the total composition, of a surfactant system, and such surfactant system preferably comprising 60% to 90%, more preferably 70% to 80% by weight of the surfactant system of an anionic surfactant.

[00103] Therefore, another subject of the present invention is the use of alkoxylated amino acid esters and / or their salts obtained by a process of the invention as detailed above, in products for fabrics and household care, in particular cleaning compositions for better removal of oily and greasy stains, removal of solid dirt such as clay, prevention of graying of fabric surfaces and / or anti-limescale agents, wherein the cleaning composition is preferably a laundry detergent formulation and / or a dishwashing detergent formulation, more preferably a liquid laundry detergent formulation and / or a liquid dishwashing detergent formulation.

[00104] Another material aspect of the present invention is therefore also a Petition 870250084807, dated 09 / 19 / 2025, page 137 / 168 / 50 cleaning composition, product for fabrics and household care, industrial and institutional cleaning product, preferably in laundry detergents, in cleaning compositions and / or in products for fabrics and household care, each comprising at least one alkoxylated amino acid ester and / or its salts obtained by a process of the invention.

[00105] A further material of the present invention is a product for fabrics and household care, a cleaning composition, an industrial and institutional cleaning product, preferably a laundry detergent, a cleaning composition and / or a product for fabrics and household care, each containing at least one alkoxylated amino acid ester and / or its salts obtained by a process of the invention.

[00106] In a preferred embodiment, it is a cleaning composition and / or product for fabrics and household care and / or an industrial and institutional cleaning product, comprising at least one alkoxylated amino acid ester and / or its salts obtained by a process of the invention. In particular, it is a cleaning composition for improved cleaning performance, especially improved primary washing, preferably a laundry detergent formulation and / or a dishwashing detergent formulation, more preferably a liquid laundry detergent formulation and / or a liquid dishwashing detergent formulation.

[00107] In a preferred embodiment, the cleaning composition of the present invention is a liquid or solid detergent composition for washing clothes, preferably a liquid detergent composition for washing clothes.

[00108] In another preferred embodiment, the cleaning composition of the present invention is a liquid or solid detergent composition (e.g., powder or tablet / unit dose) for manual or automatic washing of Petition 870250084807, dated 09 / 19 / 2025, pp. 138 / 168 / 50 dishes, preferably a liquid detergent composition for hand dishwashing. Such compositions are well known to one skilled in the art.

[00109] In another embodiment, the cleaning composition of the present invention is a hard surface cleaning composition that can be used to clean various surfaces, such as hardwood, tile, ceramic, plastic, leather, metal, glass.

[00110] In one embodiment of the present invention, the alkoxylated amino acid esters of the invention and / or their salts obtained by a process of the invention are a component of cleaning compositions or products for fabrics and household care, preferably a composition for cleaning clothes, a product for caring for clothes or a product for treating clothes or a product for washing clothes, preferably a liquid detergent formulation for washing clothes or a liquid detergent product for washing clothes, each further comprising at least one surfactant, preferably at least one anionic surfactant.

[00111] In one embodiment, it is also preferred in the present invention that the cleaning composition comprises (in addition to at least one alkoxylated amino acid ester and / or its salts obtained by a process of the invention) further at least one enzyme, preferably selected from one or more, optionally further comprising at least one enzyme, preferably selected from one or more lipases, hydrolases, amylases, proteases, cellulases, hemicellulases, phospholipases, esterases, pectinases, lactases, pectate lyases, cutinases, DNases, xylanases, oxyreductases, dispersins, mannanases and peroxidases, and combinations of at least two of the foregoing types, preferably at least one enzyme being selected from lipases.

[00112] Even more preferably, the cleaning compositions of the present invention comprising at least one amino acid ester. Petition 870250084807, dated 09 / 19 / 2025, page. 139 / 168 / 50 alkoxylated compounds of the invention and / or their salts obtained by a process of the invention and optionally further comprising at least one surfactant or a surfactant system — as detailed above — are those for improved cleaning performance in laundry and hand dishwashing applications, more specifically, for improved cleaning performance (actions as detailed above), such as those on fabrics and dishes, and may further comprise at least one enzyme selected from the list optionally further comprising at least one enzyme, preferably selected from one or more, optionally further comprising at least one enzyme, preferably selected from one or more lipases, hydrolases, amylases, proteases, cellulases, hemicellulases, phospholipases, esterases, pectinases, lactases, pectate lyases, cutinases, DNases, xylanases, oxyreductases, dispersins, mannanases and peroxidases,and combinations of at least two of the preceding types, preferably selected from one or more lipases, hydrolases, amylases, proteases, cellulases, and combinations of at least two of the preceding types, more preferably with at least one enzyme being selected from lipases.

[00113] In one embodiment, the alkoxylated amino acid esters of the invention and / or their salts obtained by a process of the invention can be used in cleaning compositions comprising a surfactant system comprising C10-C15 alkylbenzene sulfonates (LAS) as the primary surfactant and one or more additional surfactants selected from nonionic, cationic, amphoteric, zwitterionic or other anionic surfactants, or mixtures thereof.

[00114] In a further embodiment, the alkoxylated amino acid esters of the invention and / or their salts obtained by a process of the invention may be used in cleaning compositions or products for fabrics and household care, preferably a cleaning composition for Petition 870250084807, dated 09 / 19 / 2025, page 140 / 168 / 50 clothes, a product for clothing care or a product for washing clothes, preferably a liquid laundry detergent formulation or liquid laundry detergent product, comprising C12-C18 alkyl ethoxylate surfactants with 5 to 10 ethoxy units as the primary surfactant and one or more additional surfactants selected from anionic, cationic, amphoteric, zwitterionic or other non-ionic surfactants, or mixtures thereof.

[00115] In a further embodiment, the alkoxylated amino acid esters of the invention and / or their salts obtained by a process of the invention may be used in cleaning compositions or products for fabrics and household care, preferably a composition for cleaning clothes, a product for caring for clothes or a product for treating clothes or a product for washing clothes, preferably a liquid detergent formulation for washing clothes or a liquid detergent product for washing clothes, comprising linear or branched C8-C18 alkyl ether sulfates with 1 to 5 ethoxy units as the main surfactant and one or more additional surfactants selected from nonionic, cationic, amphoteric, zwitterionic or other anionic surfactants, or mixtures thereof.

[00116] In one embodiment of the present invention, the alkoxylated amino acid esters of the invention and / or their salts obtained by a process of the invention are a component of a cleaning composition, such as preferably a formulation for washing clothes or dishes, more preferably a liquid formulation for washing clothes or for hand dishwashing, each further comprising at least one surfactant, preferably at least one anionic surfactant.

[00117] In a further embodiment, this invention also encompasses a composition comprising at least alkoxylated amino acid esters and / or their salts obtained by a process of the invention, comprising Petition 870250084807, dated 09 / 19 / 2025, page 141 / 168 / 50 additionally an antimicrobial agent as described below, preferably selected from the group consisting of 2-phenoxyethanol, more preferably comprising said antimicrobial agent in an amount ranging from 2 ppm to 5% by weight of the composition; even more preferably comprising 0.1 to 2% of phenoxyethanol.

[00118] In a further embodiment, this invention also encompasses a composition, preferably a cleaning composition, more preferably a liquid detergent composition for washing clothes or a liquid composition for hand dishwashing, even more preferably a liquid detergent composition for washing clothes, or a liquid fabric softener composition for use in washing clothes, such composition comprising an alkoxylated amino acid ester and / or its salts obtained by a process of the invention in the amounts detailed before as described herein, such composition further comprising 4,4'-dichloro 2-hydroxydiphenyl ether in a concentration of 0.001 to 3%, preferably 0.002 to 1%, more preferably 0.01 to 0.6%, each by weight of the composition.

[00119] In another embodiment, this invention also encompasses a composition, specifically a cleaning composition, more preferably a cleaning composition in liquid, solid or semi-solid form, preferably a concentrated liquid detergent formulation, a single-dose laundry detergent formulation, a liquid dishwashing detergent formulation or a solid formulation for automatic dishwashing, more preferably a laundry detergent formulation, comprising alkoxylated amino acid esters and / or their salts obtained by a process of the invention and in the amounts detailed above, such composition preferably being a detergent composition, further comprising an antimicrobial agent as described. Petition 870250084807, dated 09 / 19 / 2025, p. 142 / 168 / 50 below, preferably selected from the group consisting of 2-phenoxyethanol, more preferably comprising said antimicrobial agent in an amount ranging from 2 ppm to 5% by weight of the composition; even more preferably comprising 0.1 to 2% of phenoxyethanol.

[00120] In another embodiment, this invention also encompasses a method of preserving an aqueous composition against contamination or microbial growth, such composition, specifically a cleaning composition, more preferably a cleaning composition in liquid, solid or semi-solid form, preferably being a concentrated liquid detergent formulation, a single-dose laundry detergent formulation, a liquid dishwashing detergent formulation or a solid formulation for automatic dishwashing, more preferably a laundry detergent formulation, comprising alkoxylated amino acid esters and / or their salts obtained by a process of the invention and in the quantities detailed above, such composition preferably being a detergent composition,such method comprising the addition of at least one antimicrobial agent selected from among the antimicrobial agents described below, such antimicrobial agent preferably being 2-phenoxyethanol.

[00121] In a further embodiment, this invention also encompasses a method for washing fabric or cleaning hard surfaces, wherein the method comprises treating a fabric or a hard surface with a cleaning composition, more preferably a liquid laundry detergent composition or a liquid dishwashing composition, even more preferably a liquid laundry detergent composition, or a liquid fabric softener composition for use in laundry, such composition comprising an alkoxylated amino acid ester and / or its salts obtained by a process of the invention. Petition 870250084807, dated 09 / 19 / 2025, pp. 143 / 168 / 50 in the quantities detailed above, such composition also comprising 4,4'-dichloro 2-hydroxydiphenyl ether.

[00122] As used herein, the phrase “cleaning composition”, as used for compositions and products of the invention, includes compositions and formulations designed to clean soiled material.Such compositions include, but are not limited to, compositions and detergents for cleaning clothes, fabric softening compositions, fabric improving compositions, fabric refreshing compositions, laundry pre-wash, laundry pre-treatment, laundry washing additives, spray products, dry cleaning agent or composition, laundry rinse additive, washing additive, post-rinse fabric treatment, ironing aid, dishwashing compositions, hard surface cleaning compositions, unit dose formulation, delayed dispensing formulation, detergent contained in or on a porous substrate or nonwoven sheet, and other suitable forms that may be evident to one skilled in the art by regard to the teachings in this document.These compositions can be used as a pre-wash treatment, a post-wash treatment, or can be added during the rinse or wash cycle of the laundry operation. The cleaning compositions can be in a selected form of liquid, powder, single-phase or multi-phase unit dose, bag, tablet, gel, paste, bar or flake.

[00123] The cleaning compositions of the invention comprise a surfactant system in a sufficient amount to provide the desired cleaning properties. In some embodiments, the cleaning composition comprises, by weight of the composition, from about 1% to about 70% of a surfactant system. In other embodiments, the liquid cleaning composition comprises, by weight of the composition, from about 2% to about 60% of the surfactant system. In other embodiments, the cleaning composition comprises, by weight of the composition, from about 5% to about 30% of the Petition 870250084807, dated 09 / 19 / 2025, pp. 144 / 168 / 50 surfactant system. In embodiments for a liquid or spray detergent cleaning composition for hand dishwashing, such composition preferably comprises 60% to 90%, more preferably 70% to 80% by weight of the surfactant system, most preferably of an anionic surfactant. The surfactant system may comprise a detergent surfactant selected from anionic surfactants, nonionic surfactants, cationic surfactants, zwitterionic surfactants, amphoteric surfactants, ampholytic surfactants, and mixtures thereof. Those skilled in the art will understand that a detergent surfactant encompasses any surfactant or mixture of surfactants that provides cleaning, stain removal, or washing benefits to the soiled material.

[00124] Even more preferably, the compositions or products of the present invention as detailed herein above comprising at least one alkoxylated amino acid ester of the invention and / or its salts obtained by a process of the invention and in the amounts specified in the preceding paragraph, optionally further comprising at least one surfactant or a surfactant system in amounts of about 1% to about 70% by weight of the composition or product, are preferably those for primary cleaning (i.e., stain removal) and more preferably in laundry washing applications and may further comprise at least one enzyme selected from lipases, hydrolases, amylases, proteases, cellulases, mannanases, hemicellulases, phospholipases, esterases, xylanases, DNases, dispersins, pectinases, oxidoreductases, cutinases, lactases and peroxidases, more preferably at least two of the types mentioned above.

[00125] The phrase “cleaning composition,” as used herein, includes compositions, formulations, and products designed to clean soiled material. Such compositions, formulations, and products include those intended for cleaning soiled materials or soiled surfaces of any kind.

[00126] Compositions for “industrial and institutional cleaning” include Petition 870250084807, dated 09 / 19 / 2025, pp. 145 / 168 / 50 such cleaning compositions designed for use in industrial and institutional cleaning, such as those for use in cleaning soiled materials or surfaces of any kind, such as hard surface cleaners for surfaces of any kind, including tiles, carpets, PVC surfaces, wood surfaces, metal surfaces, lacquered surfaces.

[00127] “Compositions for fabrics and household care” include cleaning compositions including, but not limited to, compositions and detergents for cleaning clothes, fabric softening compositions, compositions for improving fabrics, fabric refreshing compositions, pre-washing of clothes, pre-treatment of clothes, additives for washing clothes, spray products, dry cleaning agent or composition, laundry rinse additive, washing additive, post-rinse fabric treatment, ironing aid, dishwashing compositions, compositions for cleaning hard surfaces, unit dose formulation, delayed dispensing formulation, detergent contained in or on a porous substrate or nonwoven sheet, and other suitable forms that may be evident to one skilled in the art by regard to the teachings in this document.These compositions can be used as a pre-wash treatment, a post-wash treatment, or they can be added during the rinse or wash cycle of the washing operation, preferably during the wash cycle of the laundry or dishwashing operation.

[00128] The cleaning compositions of the invention may be in any form, namely, in the form of a liquid; a solid such as powder, granules, agglomerate, paste, tablet, pouches, bar, gel; an emulsion; types dispensed in containers with double or multiple compartments; single-phase or multi-phase unit dose; a detergent in spray or foam form; wet wipes (i.e., the cleaning composition in combination with a non-woven material, such as that discussed in US Petition 870250084807, dated 09 / 19 / 2025, pages 146 / 168 / 50 6,121,165, Mackey, et al.); dry wipes (i.e., the cleaning composition in combination with nonwoven materials, such as that discussed in US 5,980,931, Fowler, et al.) activated with water by a user or consumer; and other forms of homogeneous, non-homogeneous, or single-phase or multi-phase cleaning products.

[00129] The liquid cleaning compositions of the present invention preferably have a viscosity of 50 to 10,000 mPa*s; liquid compositions for manual dishwashing (also “liquid dishwashing compositions”) preferably have a viscosity of 100 to 10,000 mPa*s, more preferably 200 to 5,000 mPa*s and much more preferably 500 to 3,000 mPa*s at 20 1 / s and 20°C; liquid compositions for laundry preferably have a viscosity of 50 to 3,000 mPa*s, more preferably 100 to 1,500 mPa*s and much more preferably 200 to 1,000 mPa*s at 20 1 / s and 20°C.

[00130] The cleaning compositions and formulations of the invention may contain — and preferably do contain — adjunct cleaning additives (also abbreviated herein as “adjuncts”), such adjuncts preferably being additional to a surfactant system as defined above.

[00131] Suitable auxiliary cleaning additives include adjuvants, core strengtheners, structuring or thickening agents, 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, bleaching activators, bleaching catalysts, bleaches, odor control agents, pigments, dyes, opacifiers, tinting agents, dye transfer inhibitors, chelating agents, foam intensifiers, foam suppressants (antifoaming agents), color stains, care Petition 870250084807, dated 09 / 19 / 2025, pp. 147 / 168 / 50 containing silver, anti-tarnish and / or anti-corrosion agents, sources of alkalinity, pH adjusters, pH buffering agents, hydrotropes, washing particles, antibacterial agents, antioxidants, softeners, carriers, processing aids, fragrance enhancers and perfumes.

[00132] Liquid cleansing compositions may additionally comprise - and preferably do comprise - at least one of rheology control / modification agents, emollients, humectants, skin rejuvenating actives and solvents.

[00133] Solid compositions may additionally comprise, and preferably comprise, at least one of the following: fillers, bleaches, bleaching activators and catalytic materials.

[00134] Suitable examples of such cleaning adjuncts and usage levels are found in WO 99 / 05242, US Patents Nos. 5,576,282, 6,306,812 B1 and 6,326,348 B1.

[00135] Those skilled in the art will understand that a detergent surfactant encompasses any surfactant or mixture of surfactants that provides cleaning, stain removal, or washing benefits to soiled material.

[00136] Thus, the cleaning compositions of the invention, such as products for fabrics and household care, and formulations for industrial and institutional cleaning, more specifically, such as detergents for hand washing of clothes and dishes, preferably additionally comprise a surfactant system and, more preferably, also other adjuncts, as described above.

[00137] The surfactant system may consist of a surfactant or a combination of surfactants selected from anionic surfactants, nonionic surfactants, cationic surfactants, zwitterionic surfactants, amphoteric surfactants, and mixtures thereof. Those skilled in the art will understand that a surfactant system for detergents encompasses any Petition 870250084807, dated 09 / 19 / 2025, pp. 148 / 168 / 50 surfactant or mixture of surfactants that provides cleaning, stain removal or washing benefits for soiled material.

[00138] The cleaning compositions of the invention typically comprise a surfactant system in an amount sufficient to provide the desired cleaning properties.

[00139] The liquid cleaning compositions of the present invention may have any suitable pH value. Preferably, the pH of the composition is adjusted between 4 and 14. More preferably, the composition has a pH of 6 to 13, even more preferably 6 to 10, most preferably 7 to 9. The pH of the composition can be adjusted using pH-modifying ingredients known in the art and is measured as a 10% product concentration in demineralized water at 25°C. For example, NaOH can be used and the actual weight % of NaOH can be varied and cut down to the desired pH, such as pH 8.0. In one embodiment of the present invention, a pH >7 is adjusted using amines, preferably alkanolamines, most preferably triethanolamine.

[00140] The selection of additional surfactants and other ingredients in these formulations may depend on the application and the desired benefit.

[00141] All these cleaning compositions, their ingredients, including cleaning additives (adjuncts), their general compositions and more specific compositions are known, as for example illustrated in publications 800542 and 800500, as published by Protegas, Liechtenstein, and also in WO 2022 / 136409 and WO 2022 / 136408, wherein in any of the prior art documents, the (amino)steramines and their salts within the general compositions and also each individualized specific cleaning composition described in the aforementioned publications may be partially or completely replaced by the amino acid esters and / or their salts of this present invention. In these aforementioned documents, various types of are also described. Petition 870250084807, dated 09 / 19 / 2025, pp. 149 / 168 / 50 formulations for cleaning compositions; all these types of composition — the general compositions and also each specific individualized cleaning composition — can also be equally applied to the cleaning compositions contemplated herein.

[00142] Therefore, the present invention also encompasses any and all of the compositions described in the prior art descriptions mentioned above, but additionally comprising at least one of the amino acid esters of the invention and / or its salt in addition to, or as a replacement for, any existing prior art composition containing steramine or steramine salt or any such compound, which may be replaced by such amino acid ester or salt of the invention — such replacements being in principle known to a person skilled in the art or readily apparent in view of the present invention — with the content of the amino acid ester or salt of the invention being present in said formulations at a concentration generally of 0.05 to 20% by weight, preferably up to 10% by weight, more preferably 0.1 to 5% by weight, even more preferably at a concentration of 0.5 to 2% by weight. Dishwashing solutions

[00143] Another aspect of the present invention is also a dishwashing composition, comprising at least one compound of the invention as described above.

[00144] Thus, one aspect of the present invention is also the use of the compound of the invention as described above, in dishwashing applications, such as manual or automated dishwashing applications.

[00145] Dishwashing compositions according to the invention may be in the form of a liquid, semi-liquid, cream, lotion, gel or solid composition, solid embodiments including, for example, powders and tablets. Liquid compositions are typically preferred for hand dishwashing applications, while solid formulations and Petition 870250084807, dated 09 / 19 / 2025, pp. 150 / 168 / 50 formulations in bags (where the bags may also contain solids in addition to liquid ingredients) are typically preferred for compositions for automated dishwashing; however, in some areas of the world liquid compositions are also used for automated dishwashing and are therefore also covered by the term "dishwashing composition".

[00146] Dishwashing compositions are intended for direct or indirect application to dishes and metal and glass surfaces, such as glasses and other types, beakers, plates and kitchen utensils, such as pots and pans, and cutlery, such as forks, spoons, knives and the like.

[00147] The invention method for cleaning dishes, metal and / or glass surfaces comprises the step of applying the dishwashing cleaning composition, preferably in liquid form, to the surface, directly or by means of a cleaning instrument, i.e., in pure form. The composition is applied directly to the surface to be treated and / or to a cleaning device or implement such as a dishcloth, sponge or dish brush and the like without undergoing significant dilution (immediately) before application. The cleaning device or implement is preferably wetted before or after the composition is dispensed onto it. In the invention method, the composition can also be applied in diluted form.

[00148] Pure and diluted application results in superior cleaning performance, i.e., the formulations of the invention containing at least one compound of the invention exhibit excellent degreasing properties. The effort required to remove greasy and / or oily dirt from ceramic, metal and / or glass surfaces is reduced due to the presence of the compound of the invention, even when the level of surfactant used is lower than in conventional compositions. Petition 870250084807, dated 09 / 19 / 2025, pp. 151 / 168 / 50

[00149] Preferably, the composition is formulated to provide superior grease-removing (degreasing) properties, long-lasting foam, and / or improved viscosity control when exposed to reduced temperatures; preferably at least two, more preferably all three properties are present in the dishwashing composition of the invention. Other optional benefits – preferably present – ​​of the composition of the invention for hand dishwashing include dirt removal, shine, and / or hand care; more preferably at least two and more preferably all three additional benefits are present in the dishwashing composition of the invention.

[00150] In one embodiment of the present invention, the compound of the invention is a component of a hand dishwashing formulation that further comprises at least one surfactant, preferably at least one anionic surfactant.

[00151] In another embodiment of the present invention, the compound of the invention is a component of a hand dishwashing formulation that further comprises at least one anionic surfactant and at least one other surfactant, preferably selected from amphoteric and / or zwitterionic surfactants. In a preferred embodiment of the present invention, the hand dishwashing formulations contain at least one amphoteric surfactant, preferably an amine oxide, or at least one zwitterionic surfactant, preferably a betaine, or mixtures thereof, to aid in the foaming, detergency and / or softness of the detergent composition. Liquid composition for hand dishwashing

[00152] The liquid detergent composition comprising steramine technology, according to the invention, can be a detergent composition for hand dishwashing or in spray form. Petition 870250084807, dated 09 / 19 / 2025, pp. 152 / 168 / 50 Preferably, the liquid dishwashing detergent composition for hand washing or spray comprises between 0.1% and 50%, preferably between 1% and 30% by weight of the detergent composition comprising the steramine technology, according to the invention. Preferably, the pH of the detergent composition of the invention, measured as a 10% product concentration in demineralized water at 20°C, is adjusted to between 3 and 14, more preferably between 4 and 13, most preferably between 6 and 12, and even more preferably between 8 and 10. The composition of the present invention may be Newtonian or non-Newtonian, preferably Newtonian. Preferably, the composition has a viscosity of 10 mPa^s to 10,000 mPa^s, preferably from 100 mPa^s to 5,000 mPa^s, more preferably from 300 mPa^s to 2,000 mPa^s, or even more preferably from 500 mPa^s to 1,500 mPa^s, alternatively combinations thereof.Viscosity is measured at 20°C with a Brookfield RT viscometer using shaft 31, with the viscometer rotation adjusted to achieve a torque between 40% and 60%. The viscosity of the spray detergent preferably ranges from 0.5 to 100 mPa^s.

[00153] The spray or liquid detergent cleaning composition for hand dishwashing comprises from 0.1% to 50%, preferably from 1% to 35%, more preferably from 3% to 30%, by weight, of the total composition of a surfactant system. The surfactant system preferably comprises from 60% to 90%, more preferably from 70% to 80%, by weight, of the surfactant system of an anionic surfactant. Alkyl sulfate anionic surfactants are preferred, particularly those selected from the group consisting of: alkyl sulfate, alkylalkoxy sulfate, preferably alkylhexyl sulfate, alkyl ethoxy sulfate, and mixtures thereof.The anionic alkyl sulfate surfactant preferably has an average alkyl chain length of 8 to 18, preferably 10 to 14, more preferably 12 to 14, and even more preferably 12 to 13 carbon atoms. The anionic alkyl sulfate surfactant preferably has a medium degree of alkyl sulfate. Petition 870250084807, dated 09 / 19 / 2025, pp. 153 / 168 / 50 of alkoxylation, preferably ethoxylation, less than 5, preferably less than 3, more preferably from 0.5 to 2.0, much more preferably from 0.5 to 0.9. The anionic alkyl sulfate surfactant preferably has a weight-average degree of branching greater than 10%, preferably greater than 20%, more preferably greater than 30%, even more preferably between 30% and 60%, much more preferably between 30% and 50%. Suitable counterions include alkali metal cation, alkaline earth metal cation, alkanol ammonium or ammonium or substituted ammonium, but preferably sodium. Suitable examples of commercially available anionic alkyl sulfate surfactants include those derived from alcohols sold under the brand name Neodol® by Shell, or the brands Lial®, Isalchem® and Safol® by Sasol, or some of the natural alcohols produced by Procter & Gamble Chemicals.

[00154] The surfactant system preferably comprises from 0.1% to 20%, more preferably from 0.5% to 15%, and especially from 2% to 10% by weight of the liquid dishwashing detergent composition of a co-surfactant. Preferred co-surfactants are selected from the group consisting of an amphoteric surfactant, a zwitterionic surfactant, and mixtures thereof. The weight ratio between anionic surfactant and co-surfactant can be from 1:1 to 8:1, preferably from 2:1 to 5:1, more preferably from 2.5:1 to 4:1. The co-surfactant is preferably an amphoteric surfactant, more preferably an amine oxide surfactant. Preferably, the amine oxide surfactant is selected from the group consisting of: alkyl dimethyl amine oxide, alkyl amido propyl dimethyl amine oxide and mixtures thereof, more preferably C12-C14 alkyl dimethyl amine oxide.Suitable zwitterionic surfactants include betaine surfactants, preferably cocamidopropyl betaine.

[00155] The surfactant system of the composition of the present invention may comprise from 0.1% to 25%, preferably from 0.5% to 20%, more Petition 870250084807, dated 19 / 09 / 2025, pp. 154 / 168 / 50 preferably from 1% to 10%, and even more preferably from 1.5% to 5%, by weight of the surfactant system, of a nonionic surfactant. Suitable nonionic surfactants may be selected from the group consisting of: alkoxylated nonionic surfactant, alkyl polyglycoside surfactant (“APG”) and mixtures thereof. Suitable alkoxylated nonionic surfactants may be linear or branched, primary or secondary, alkyl alkoxylated, preferably alkyl ethoxylated nonionic surfactants, comprising, on average, 9 to 15, preferably 10 to 14 carbon atoms in their alkyl chain and, on average, 5 to 12, preferably 6 to 10, more preferably 7 to 8 ethylene oxide units per mole of alcohol.More preferably, the alkyl polyglycoside surfactant has an average alkyl carbon chain length between 10 and 16, preferably between 10 and 14, more preferably between 12 and 14, with an average degree of polymerization between 0.5 and 2.5, preferably between 1 and 2, more preferably between 1.2 and 1.6. C8C16 alkyl polyglycosides are commercially available from various suppliers (e.g., Simusol® surfactants from Seppic Corporation; and Glucopon® 600 CSUP, Glucopon® 650 EC, Glucopon® 600 CSUP / MB and Glucopon® 650 EC / MB from BASF Corporation).

[00156] The detergent composition described herein may optionally comprise a number of other auxiliary ingredients, such as boosters (e.g., preferably citrate), chelating agents (e.g., preferably GLDA), conditioning polymers, cleaning polymers, including polyalkylene imines, surface-modifying polymers, flocculant polymers, foaming polymers, including EO-PO-EO triblock copolymers, grease-cleaning amines, including cyclic polyamines, structuring agents, emollients, humectants, skin-rejuvenating actives, enzymes, carboxylic acids, exfoliating particles, bleaches and bleach activators, perfumes, and odor control agents. Petition 870250084807, dated 09 / 19 / 2025, page 155 / 168 / 50 odor, pigments, dyes, opacifiers, spheres, pearlescent particles, microcapsules, organic solvents, inorganic cations, such as alkaline earth metals, such as Ca / Mg ions, antibacterial agents, preservatives, viscosity adjusters (e.g., salt, such as NaCl, and other mono-, di- and trivalent salts) and pH adjusters and buffering agents (e.g., carboxylic acids, such as citric acid, HCl, NaOH, KOH, alkanolamines, phosphoric and sulfonic acids, carbonates, such as sodium carbonates, bicarbonates, sesquicarbonates, borates, silicates, phosphates, imidazole and the like).

[00157] It is preferred that within the respective laundry detergent, cleaning composition and / or fabric and household care product, at least one steramine and / or salt thereof, as described in this invention, is present in a concentration of about 0.1% to about 10%, preferably about 0.2% to 5%, more preferably about 0.5% to about 5%, all relative to the total weight of such composition or product, and all intermediate numbers, and including all ranges resulting from the selection of any of the aforementioned lower limits and further including 0.2, 0.3, 0.4, 1, 1.5, 2, 2.5, 3, 3.5 and 4, and combining with any of the aforementioned upper limits and including 19, 18, 17, 16, 14, 13, 12, 11, 9, 8, 7 and 6.

[00158] Specifically for a liquid or spray detergent composition for hand dishwashing, at least one steramine and / or a salt thereof, as described in this invention, is present in a concentration between 0.1 and 50%, preferably between 1% and 30%, by weight of the detergent composition.

[00159] The specific embodiments described throughout this description are covered by the present invention as part of this invention; the various additional options being described in this descriptive report as options. Petition 870250084807, dated 09 / 19 / 2025, pp. 156 / 168 / 50 “optional”, “preferred”, “more preferred”, “even more preferred” or “much more preferred” features of a specific embodiment may be individually and independently selected (unless such independent selection is not possible by virtue of the nature of that feature or if such independent selection is explicitly excluded) and then combined within any of the other embodiments (where other options and preferences may also be selected individually and independently), with each and all of these possible combinations being included as part of this invention as individual embodiments, and especially with the preferred embodiments described in the following section. Examples Methods

[00160] 1H NMR measured in MeOD with Bruker spectrometer Advance to 400 MHz.

[00161] From the NMR data and, specifically, the peaks / intervals mentioned, the respective conversion rate can be calculated using known means.

[00162] Hydroxide values ​​are determined in accordance with DIN 53240-1:2016. Table 1. Example alkoxylated alcohol - amino acid + sulfuric acid 1 Lutensol XP30 + L-Alanine + sulfuric acid 2 Lutensol XP30 + Valine + sulfuric acid 3 Dehydol LS 2 + Valine + sulfuric acid 4 Dehydol LS 2 + L-Alanine + sulfuric acid 5 Phenoxyethanol + Valine + sulfuric acid Dehydol LS 2 = Alkoxylated C12-C14 alcohol with (on average) 2 EO / OH Lutensol XP30 = 2-Propylheptanol, alkoxylated with (on average) 3 EO / OH Example 1: L-alanine - triethylene glycol-2-propyleptylether ester as sulfuric acid salt of triethylene glycol-2-propylheptylether

[00163] In a 4-necked container with a thermometer, reflux condenser, nitrogen inlet, addition funnel, and stirrer, 152.5 g of ethoxylated 2-propylheptanol were added with 3 moles of oxide Petition 870250084807, dated 09 / 19 / 2025, pp. 157 / 168 / 50 ethylene (Lutensol® XP30), 0.4 g of hypophosphorous acid (50% in water), 22.3 g of L-alanine, and 4.5 g of water. 26.1 g of concentrated sulfuric acid were added over 15 minutes. The temperature rose from room temperature to 59°C during the addition. The reflux condenser was replaced with a distillation head, and the reaction mixture was heated to 135°C bath temperature and stirred for 20 hours under a constant flow of nitrogen bubbling through the reaction mixture. The water was removed by distillation from the reaction mixture. To complete the reaction, a vacuum (1 kPa (10 mbar)) was applied, and the mixture was stirred for 8 h under vacuum at 135°C. 175.0 g of a brown oil were obtained. 1H NMR in MeOD indicated complete conversion to L-alanine - triethylene glycol-2-propyl heptyl ether ester as a sulfuric acid salt of triethylene glycol-2-propyl heptyl ether.At d = 3,94.5 ppm, a broad multiplet was identified for esterified and sulfated CH2-OH groups and protons at C2 of alanine. Example 2: L-valine - triethylene glycol-2-propyleptylether ester as sulfuric acid salt of triethylene glycol-2-propylheptylether

[00164] In a four-necked vessel with a thermometer, reflux condenser, nitrogen inlet, addition funnel, and stirrer, 152.5 g of 2-propyl-heptanol ethoxylate with 3 moles of ethylene oxide (Lutensol® XP30), 0.4 g of hypophosphorous acid (50% in water), 29.8 g of L-valine, and 4.0 g of water were added. 26.1 g of concentrated sulfuric acid were added over 15 minutes. The temperature rose from room temperature to 55°C during the addition. The reflux condenser was replaced with a distillation head, and the reaction mixture was heated to 135°C bath temperature and stirred for 23 hours under a constant flow of nitrogen bubbling through the reaction mixture. The water was removed by distillation from the reaction mixture. 160.0 g of a brown oil was obtained. 1H NMR in MeOD indicated 94% conversion to L-valine - triethylene glycol-2-propyl heptyl ether ester as a sulfuric acid salt of Petition 870250084807, dated 09 / 19 / 2025, pp. 158 / 168 / 50 triethylene glycol-2-propyl-heptyl ether. At d = 3.9-4.5 ppm, a broad multiplet was identified for esterified and sulfated CH2-OH groups. Example 3: L-valine-diethylene glycol-C12 / C14 alkyl ester as salt of C12 / C14 alkylsulfuric acid-diethylene glycol

[00165] In a four-necked vessel with a thermometer, reflux condenser, nitrogen inlet, addition funnel, and stirrer, 151.4 g of ethoxylated C12 / C14 fatty alcohol with 2 moles of ethylene oxide (hydroxyl value 194 mgKOH / g), 0.4 g of hypophosphorous acid (50% in water), 29.3 g of L-valine, and 4.5 g of water were added. 26.1 g of concentrated sulfuric acid were added over 15 minutes. The temperature rose from room temperature to 43°C during the addition. The reflux condenser was replaced with a distillation head, and the reaction mixture was heated to 135°C bath temperature and stirred for 8 hours under a constant flow of nitrogen bubbling through the reaction mixture. The water was removed by distillation from the reaction mixture. A vacuum (1 kPa (10 mbar)) was applied and the reaction mixture was stirred for a further 4 hours under vacuum to complete the conversion. 164.7 g of a brown oil were obtained.1H NMR in MeOD indicated 94% conversion to C12 / C14 L-valine-diethylene glycol-alkyl ester as a C12 / C14 alkylsulfuric acid salt of diethylene glycol. At d = 3.9-4.5 ppm, a broad multiplet for esterified and sulfated CH2-OH groups was identified. Example 4: L-alanine-diethylene glycol-C12 / C14 alkyl ester as salt of C12 / C14 alkylsulfuric acid-diethylene glycol

[00166] In a four-necked flask with a thermometer, reflux condenser, nitrogen inlet, addition funnel, and stirrer, 151.4 g of ethoxylated C12 / C14 fatty alcohol with 2 moles of ethylene oxide (hydroxyl value 194 mgKOH / g), 0.4 g of hypophosphorous acid (50% in water), 22.3 g of L-alanine, and 4.5 g of water were added. 26.1 g of concentrated sulfuric acid were added over 15 minutes. The temperature rose from Petition 870250084807, dated 09 / 19 / 2025, page 159 / 168 / 50 ambient temperature to 45°C during the addition. The reflux condenser was replaced with a distillation head, and the reaction mixture was heated to 135°C bath temperature and stirred for 11 hours under a constant flow of nitrogen bubbling through the reaction mixture. Water was removed by distillation from the reaction mixture. 162.0 g of a brown oil were obtained. 1H NMR on MeOD indicated 93% conversion to C12 / C14 lalanine-diethylene glycol-alkyl ester as a C12 / C14 alkylsulfuric acid salt of diethylene glycol. At d = 3.9-4.5 ppm, a broad multiplet was identified for esterified and sulfated CH2-OH groups and protons at C2 of alanine. Example 5: β-alanine-diethylene glycol-C12 / C14 alkyl ester as a salt of C12 / C14 alkylsulfuric acid-diethylene glycol

[00167] In a four-necked vessel with a thermometer, reflux condenser, nitrogen inlet, addition funnel, and stirrer, 95.5 g of ethoxylated C12 / C14 fatty alcohol with 2 moles of ethylene oxide (hydroxyl value 194 mgKOH / g), 0.25 g of hypophosphorous acid (50% in water), 14.1 g of β-alanine, and 2.8 g of water were added. 16.5 g of concentrated sulfuric acid were added over 15 minutes. The temperature rose from room temperature to 37°C during the addition. The reflux condenser was replaced with a distillation head, and the reaction mixture was heated to 135°C bath temperature and stirred for 8 hours under a constant flow of nitrogen bubbling through the reaction mixture. The water was removed by distillation from the reaction mixture. 100.8 g of a brown solid were obtained. 1H NMR on MeOD indicated 96% conversion to C12 / C14 β-alanine diethylene glycol alkyl ester as a C12 / C14 alkylsulfuric acid salt of diethylene glycol.At d = 3.9-4.4 ppm, a broad multiplet was identified for esterified and sulfated CH2-OH groups. Example 6: L-valine - phenoxyethanol ester as a sulfuric acid salt Petition 870250084807, dated 09 / 19 / 2025, pp. 160 / 168 / 50

[00168] In a four-necked vessel with a thermometer, reflux condenser, nitrogen inlet, addition funnel, and stirrer, 145.1 g of phenoxyethanol, 0.5 g of hypophosphorous acid (50% in water), 58.6 g of L-valine, and 9.0 g of water were added. 52.1 g of concentrated sulfuric acid were added over 15 minutes. The temperature rose from room temperature to 60°C during the addition. The reflux condenser was replaced with a distillation head, and the reaction mixture was heated to 135°C bath temperature and stirred for 6 hours under a constant flow of nitrogen bubbling through the reaction mixture. The water was removed by distillation from the reaction mixture. To complete the reaction, a vacuum (1 kPa (10 mbar)) was applied, and the mixture was stirred for 6 h under vacuum at 135°C. 220.0 g of a yellow oil were obtained. 1H NMR on MeOD indicated 89% conversion to L-valine - phenoxyethanol ester as a sulfuric acid phenoxyethanol salt.At d = 4.4-4.7 ppm, two multiplets for esterified CH2-OH groups were identified, and at d = 4.1-4.3 ppm, one multiplet for sulfated CH2-OH and phenyl-O-CH2- groups was detected.

[00169] The following is an example of a liquid detergent formulation for hand dishwashing, in which the technology in question is included in more detail. The formulation can be prepared by means of standard mixing of the individual components, according to known procedures. Table 2. Ingredients (as 100% active) Composition of the invention (in percentage) Anionic surfactant C12 / 13 AE0.6S (Average branching: 37.84%) 19.6 Dimethylamine oxide C12 / 14 6.5 Alcohol ethoxylate non-ionic surfactant (Neodol 91 / 8) 1.0 Alkoxylated polyethyleneimine (PEI600EO24PO16) 0.2 Ethanol 2.4 NaCl 0.7 Polypropylene glycol (mol weight Mw 2000 g / mol) 0.9 Steramine of the invention 0.05-5 Water + Secondary ingredients (perfume, colorant, preservatives) Equilibrium to 100 pH (with 10% concentration of the product in demineralized water — with NaOH adjustment) 9.0

Claims

1. Process for producing an organoether sulfate salt of an alkoxylated amino acid ester (“AES”), characterized in that it comprises the steps of (i) reacting at least one alpha-amino acid and at least one alkoxylated alcohol with sulfuric acid in an aqueous solution; and (ii) optionally removing water and / or removing excess alcohol.

2. Process according to claim 1, characterized in that it comprises the steps of (A) providing at least one alcohol containing a hydroxyl group, wherein such hydroxyl group is alkoxylated with at least a fraction of alkylene oxide, preferably up to 200, more preferably up to 100, more preferably up to 50, even more preferably up to 20, as up to 15 or even up to 10 moles of alkylene oxide per hydroxyl group; (B) providing at least one alpha-amino acid, and (C) sulfuric acid, wherein the molar ratios are at least as follows: - the ratio of amino acid to hydroxyl groups of the alkoxylated alcohol is at least 1:2 or 1:[more than 2]; - ​​the ratio of sulfuric acid to amino acid is 0.9:1 to 1.1:1; - the ratio between hydroxyl groups of alkoxylated alcohol and sulfuric acid is at least 2:1 and preferably (>2):1;(e) the molar ratio of water to amino acid is from 0.1:1 to 10:1, preferably up to 5:1, more preferably up to 2:1, and much more preferably up to 1:1, and most preferably from 0.5:1, as about 1:1 and exactly 1:1; (D) react the at least one alkoxylated alcohol with the at least one alpha-amino acid in the presence of sulfuric acid to obtain the AES; Petition 870250084807, dated 19 / 09 / 2025, p. 162 / 168 2 / 6 (E) optionally remove water and / or excess alcohol during and optionally also after the reaction to obtain the purified AES; and (F) optionally neutralize and purify the AES to obtain the alkoxylated amino acid esters (“AAE”).

3. A process according to any of the preceding claims, characterized in that at least one of the following process steps is carried out, preferably both: i) inerting the reaction mixture before and / or during the reaction, preferably before the addition of sulfuric acid, such inerting being carried out using a gas vapor, such as nitrogen or argon, and / or by adding an oxygen-scavenging compound, such as at least one hypophosphorous compound, preferably hypophosphorous acid; and / or ii) removing water and / or alkoxylated alcohol during and, optionally, also after the reaction, by applying a gas stream and / or applying a distillation, preferably a distillation, more preferably under reduced pressure and / or at elevated temperature, preferably both.

4. Process according to any of the preceding claims, characterized in that the reaction is carried out - at a temperature of 50 to 200°C, preferably 100 to 200°C, more preferably 120°C to 180°C, most preferably 120°C to 150°C, such as 60, 70, 80, 90, 110, 115, 120, 125, 130, 135, 140, 145, 160, 170, 190°C; - for a period of 1 to 30, preferably 2, more preferably 3 hours, and preferably up to 20, more preferably up to 165, even more preferably up to 10 hours, as preferably from 3 to 24, more preferably from 5 to 24, much more preferably from 10 to 24 hour(s); and Petition 870250084807, dated 19 / 09 / 2025, p.163 / 168 3 / 6 - at a pressure of 0.1 to 1000 kPa (0.001 to 10 bar), such as 10 (0.1), more preferably 100 (1), and preferably up to 800 (8), more preferably up to 500 (5), even more preferably up to 400 kPa (4 bar), such as 100 to 1000 (1 to 10), more preferably 100 to 500 (1 to 5), even more preferably 100 to 400 kPa (1 to 4 bar).

5. A process according to any of the preceding claims, characterized in that at least one alkoxylated alcohol is selected from among alkoxylated monoalcohols, such as C1 to C36 alkanols, preferably selected from the group comprising C2 to C36 linear alcohols, such as a mixture of these alcohols selected from C6 to C22 fatty alcohols, preferably C8 to C22 fatty alcohols, more preferably C12 and C14 fatty alcohols, more preferably C16 and C18 fatty alcohols; C3 to C36 branched alcohols, such as 2-ethylhexanol, 2-propylheptanol, isotridecanol, isononanol, C9-C17 oxoalcohols; C3 to C36 alkoxylated branched alcohols, such as alkoxylated 2-ethylhexanol, alkoxylated 2-propylheptanol, alkoxylated isotridecanol, alkoxylated isononanol, alkoxylated C9 to C17 oxoalcohols; and alkoxylated phenoxyalkanols, such as alkoxylated phenoxyethanol;with alcohols preferably selected from the group of C2 to C22 linear alkoxylated monoalcohols, more preferably a C12 to C14 linear alkoxylated monoalcohol and / or alkoxylated 2-propyl-heptanol.

6. Process according to any of the preceding claims, characterized in that at least one amino acid is selected from any alpha-amino acid, such as alanine, glycine, leucine, isoleucine, valine, proline, phenylalanine, arginine, asparagine, aspartic acid, aspartate, glutamine, glutamate, histidine, lysine, threonine, tryptophan, tyrosine, cysteine, methionine, serine; alpha-amino acids with secondary or tertiary amino groups, such as sarcosine, N,N-dimethylglycine; preferably alanine, valine, glycine, leucine, isoleucine, Petition 870250084807, dated 09 / 19 / 2025, p. 164 / 168 4 / 6 phenylalanine, more preferably alanine, valine, leucine, much more preferably alanine and valine.

7. A process according to any of the preceding claims, characterized in that at least one alkoxylated alcohol comprises at least one alkylene oxide selected from C2 to C22 alkylene oxides, preferably C2-C4 alkylene oxides, while the fractions derived from the alkylene oxide(s) may be arranged in random order, in block or multiblock, or combinations thereof, preferably as a block.

8. Process according to claim 7, characterized in that the alkoxylated alcohol comprises at least one alkylene oxide being ethylene oxide and / or propylene oxide, preferably the respective alcohol comprises at least one block based on ethylene oxide and / or propylene oxide, even more preferably containing i) only one block consisting of ethylene oxide or ii) two blocks with the first block — preferably the “inner block” directly attached to the hydroxy group of the alcohol — consisting of ethylene oxide and a second block — preferably being the “outer block attached to the ethylene oxide block” — consisting of propylene oxide, wherein preferably the EO block comprises at least 2 fractions derived from EO and the PO block comprises at least 2 fractions derived from PO.

9. A process according to any of the preceding claims, characterized in that the alkylene oxide used comprises at least 10%, at least 20%, at least 40%, at least 70%, at least 95%, and more preferably up to 100% based on carbon atoms derived from non-fossil sources.

10. Process according to any of the preceding claims, characterized in that no additional organic solvent is introduced into the reaction, apart from the organic solvents possibly present in any of the starting materials used, namely, in sulfuric acid, amino acid(s) and alkoxylated alcohol(s).

11. Alkoxylated amino acid ester (“AAE”) or its organoether sulfate salt (“AES”), characterized in that it is obtained by a process as defined in any one of claims 1 to 10.

12. Use of at least one alkoxylated amino acid ester (AEE) and / or at least one organoether sulfate salt of an alkoxylated amino acid ester (AES) as defined in claim 11, characterized in that it is in a cleaning composition, fabric and household care product, industrial and institutional cleaning product, cosmetic or personal care product.

13. Use according to claim 12, characterized by being in cleaning compositions and / or in products for fabrics and household care, preferably in a fabric detergent formulation or a dishwashing detergent formulation, more preferably in a hand dishwashing detergent formulation.

14. Composition, characterized in that it comprises at least one AAE and / or at least one AES obtainable by a process as defined in any one of claims 1 to 10.

15. Composition according to claim 14, characterized in that it is a cleaning composition, a fabric and household care product, an industrial and institutional cleaning product, a cosmetic or personal care product, preferably a fabric detergent formulation or a dishwashing detergent formulation, more preferably a hand dishwashing detergent formulation, wherein at least one AAE and / or at least one AES is present in the composition / product at a concentration of about 0.1% to about 50%, preferably from about 0.25% to 15%, plus Petition 870250084807, dated 09 / 19 / 2025, p. 166 / 168 6 / 6 preferably from about 0.5% to about 10% and even more preferably from about 0.5% to about 5%, and much more preferably in amounts up to 3%, each in % by weight relative to the total weight of such composition / product,optionally further comprising from about 1% to about 70% by weight of a surfactant system, wherein, for a liquid dishwashing or spray detergent cleaning composition for hand washing, such composition comprises from 0.1% to 50%, preferably from 1% to 35%, more preferably from 3% to 30%, by weight of the total composition of a surfactant system, such surfactant system preferably comprising from 60% to 90%, more preferably from 70% to 80%, by weight, of the surfactant system of an anionic surfactant, optionally further comprising at least one enzyme, preferably selected from one or more lipases, hydrolases, amylases, proteases, cellulases, mannanases, hemicellulases, phospholipases, esterases, xylanases, DNases, dispersins, pectinases, oxidoreductases, cutinases, lactases and peroxidases,More preferably, at least two of the types mentioned above; optionally further comprising an antimicrobial agent selected from the group consisting of 2-phenoxyethanol; preferably comprising said antimicrobial agent in an amount ranging from 2 ppm to 5% by weight of the composition; more preferably comprising 0.1 to 2% of phenoxyethanol; optionally further comprising 4,4'-dichloro-2-hydroxydiphenyl ether in a concentration of 0.001 to 3%, preferably 0.002 to 1%, most preferably 0.01 to 0.6%, each by weight of the composition.