Substituted 1,3-dioxolane sulfates and uses thereof

Abstract

Substituted 1,3-dioxolane sulfates and uses thereof The present invention relates to substituted 1,3-dioxolane sulfates according to formula (I), methods of their manufacture and uses, for example in laundry or dishwashing.

Description

[0001] This invention relates to specific 1,3-dioxolane sulfates comprising the structure according to formula (I) (in this invention, whenever referring to a compound of the invention, it is abbreviated as "compound of the invention" or "compound of the invention"), methods of manufacturing thereof, uses thereof, and compositions comprising compounds of the invention, particularly laundry detergent compositions.

[0002] Anionic surfactants (especially sulfonates such as linear alkylbenzene sulfonates (LAS) and sulfates such as primary alkyl sulfates (PAS)) are key ingredients in modern laundry detergents, providing excellent cleaning performance against a wide range of dirt and stains.

[0003] However, detergent formulators continue to face the task of improving the environmental “footprint” of any product, whether in terms of its source, such as from natural or renewable resources, or in terms of production efficiency compared to previous products, thus reducing energy use, usage efficiency such as reducing dosage for the same performance or improving performance at the same dosage level, persistence in the natural environment after use, and especially in terms of biodegradability, because recycling is technically very challenging and therefore not economically attractive.

[0004] Therefore, due to climate change, one of the most important goals for the detergent and cleaning products (D&C) industry today is to significantly reduce CO2 emissions per wash. Surfactants such as LAS and PAS are based on fossil carbon sources, and therefore their production is incompatible with the D&C industry's environmentally friendly goals. To overcome this problem, alternative surfactants that provide significant washing performance and (or potentially) are based on non-fossil carbon sources are of interest to the D&C industry.

[0005] One such alternative surfactant group with a structure roughly similar to LAS is 1,3-dioxolane sulfates.

[0006] The following provides an overview of the current knowledge and most relevant disclosures in the field of this invention, the synthesis and uses of 1,3-dioxolane sulfates and similar compounds.

[0007] US 10822323 A describes an acid-insecure surfactant comprising a surfactant based on 1,3-dioxane- or 1,3-dioxolane. In detail, this application discloses the advantages of acid-insecure surfactants and proposes their use in protein gel separation (SDS-PAGE). Compared to the compounds of this invention, US 10822323 A describes a compound having a two-carbon-atom sulfated linker; however, this linker is attached at position 2 of the 1,3-dioxolane ring. A longer alkyl group is attached at position 4, but contains heteroatoms such as O, S, and NH.

[0008] US 3948953 A discloses 1,3-dioxolane derivatives with surfactant properties. For these compounds, their roles as components in detergent compositions and as organic intermediates, particularly pharmaceutical intermediates, are described. They are obtained by reacting a ketone with glycerol, followed by further modification (sulfation or ethoxylation). Therefore, these compounds differ from the inventive compounds of this application in that they do not contain at least two carbon atoms in the linker carrying the sulfate ester group at position 4 of the 1,3-dioxolane ring.

[0009] US 20230174897 A and US 20230174897 A describe liquid manual dishwashing detergent compositions comprising a mixture of surfactants based on sulfated 1,3-dioxane and surfactants based on sulfated 1,3-dioxolane, obtained by converting aliphatic aldehydes with glycerol followed by sulfation. Furthermore, these compounds contain a sulfated linker containing only one carbon atom at position 4 of the 1,3-dioxolane ring.

[0010] Compared to US 3948953 A, US 20230174897 A, and US 20230174897 A, the compounds of the present invention are not synthesized by reacting a ketone with glycerol, but rather by reacting a ketone with a straight-chain triol containing 4 to 12 carbon atoms, wherein the hydroxyl groups are at the 1-, 2-, and ω-positions. Reacting this triol with an aldehyde or ketone produces a surfactant having a linker containing at least two carbon atoms at position 4 of the dioxolane ring. Compared to prior art compounds containing linkers with only one carbon atom, the compounds of the present invention demonstrate significantly improved foaming properties and dynamic surface tension, as shown experimentally.

[0011] Therefore, the inventors of this invention have unexpectedly discovered that extending the sulfated alkyl linker at position 4 results in improved detergency of surfactants based on sulfated 1,3-dioxolane, while maintaining the possibility of synthesizing these compounds using renewable and commercially available extracts.

[0012] Therefore, the object of the present invention is to provide a novel compound having a structure according to formula (I).

[0013] Formula (I)

[0014] in

[0015] R1 is a C8 to C27 alkyl or C8 to C27 alkenyl.

[0016] R4 is hydrogen, a C2 to C18 alkyl group, or a C2 to C18 alkenyl group.

[0017] R2 is (i) (ii) 、or (iii) ,

[0018] M is selected from the following groups: hydrogen, Na, K, ammonia, protonated amines, and protonated amino alcohols;

[0019] m is an integer with values ​​from 1 to 4;

[0020] The dashed lines indicate the bonds bonded to the oxygen atom in formula (I), and

[0021] n is an integer with values ​​from 1 to 9.

[0022] In another aspect, the present invention relates to a method for preparing the compound of the present invention, the method comprising:

[0023] i) Make the aldehyde or ketone according to formula (II)

[0024] Equation (II),

[0025] Wherein R3 is a C8 to C27 alkyl or C8 to C27 alkenyl, and

[0026] R4 is hydrogen, a C2 to C18 alkyl group, or a C2 to C18 alkenyl group.

[0027] It reacts with straight-chain triols containing 4 to 12 carbon atoms, wherein the hydroxyl groups are at the 1-, 2-, and ω-positions, in the presence of an acidic catalyst.

[0028] To obtain the compound of the present invention, wherein R2 is And the dashed line is as defined above, and optionally...

[0029] ii) The compound in step i) is sulfated or sulfonated and then neutralized with a base selected from the group consisting of sodium hydroxide or potassium hydroxide, ammonia, amines, and amino alcohols.

[0030] To obtain the compound of the present invention, wherein R2 is or And M, m and the dashed line are as defined above.

[0031] Furthermore, (cleaning) compositions containing compounds of the present invention are also part of the present invention.

[0032] In addition, the present invention relates to a cleaning method and the use of the compounds of the present invention in a (cleaning) composition.

[0033] Therefore, the subject matter of the present invention is the following embodiments 1 to 15, as defined below and further explained by other examples and illustrated further in the experimental section:

[0034] Example 1

[0035] A compound having a structure according to formula (I)

[0036] Formula (I)

[0037] in

[0038] R1 is a C8 to C27 alkyl or C8 to C27 alkenyl.

[0039] R4 is hydrogen, a C2 to C18 alkyl group, or a C2 to C18 alkenyl group.

[0040] R2 is (i) (ii) 、or (iii) ,

[0041] M is selected from the following groups: hydrogen, Na, K, ammonia, protonated amines, and protonated amino alcohols;

[0042] m is an integer with values ​​from 1 to 4;

[0043] The dashed lines indicate the bonds bonded to the oxygen atom in formula (I), and

[0044] n is an integer with values ​​from 1 to 9.

[0045] The compounds of the present invention according to formula (I) can be synthesized by reacting a straight-chain triol containing 4 to 12 carbon atoms (wherein the hydroxyl groups are at the 1-, 2-, and ω-positions) with an aldehyde (resulting in R4 being hydrogen) or a ketone (resulting in R4 being a C2 to C18 alkyl or C2 to C18 alkenyl). In a preferred embodiment, R4 is hydrogen, which means reacting the triol with an aldehyde.

[0046] In a preferred embodiment, R1 is at least C9, at least C10, at least C11, at least C12, at least C13, at least C14, at least C15, at least C16 or at least C17 alkyl or alkenyl and not exceeding C26, not exceeding C25, not exceeding C24, not exceeding C23, not exceeding C22, not exceeding C21, not exceeding C20, not exceeding C19 or not exceeding C18 alkyl or alkenyl.

[0047] In a preferred embodiment, R4 is at least C3, at least C4, at least C5, at least C6, at least C7, at least C8, at least C9, at least C10 or at least C11 alkyl or alkenyl and not more than C17, not more than C16, not more than C15, not more than C14, not more than C13, not more than C12 alkyl or alkenyl.

[0048] Those skilled in the art will recognize that the compounds of the present invention can form the basis for other reactions, particularly by modifying the reactions of the compounds of the present invention by substituting hydrogen atoms with functional groups such as additional alkyl or alkylene groups, nitrogen-containing groups, -OH groups, -CHO groups, -COOH groups, -SO4 groups or variants or combinations thereof.

[0049] In a preferred embodiment, the compounds of the present invention do not contain any such functional modifications, particularly functional groups such as nitrogen-containing groups, -OH groups, -CHO groups, -COOH groups, sulfur-containing groups, or variations or combinations thereof.

[0050] As used herein, "protonated amine" means any protonated amine, i.e., ammonium, primary amine, secondary amine, and tertiary amine. Amines that can be protonated and can form salts with the compounds of this invention include methylamine, ethylmethylamine, and trimethylamine.

[0051] As used herein, the term "amino alcohol" refers to a chemical entity containing both an amino and a hydroxyl moiety. Those skilled in the art know that the amino group of these compounds can be protonated.

[0052] The substructure "-OM" of formula (I) can refer to a salt as well as the interaction between anion and cation. In the case that the compound of the present invention is a salt, "M" is a cation, and "O" is negatively charged and thus forms an anion. Alternatively, "O" can be covalently bonded to a hydrogen atom and therefore does not form a salt.

[0053] “m” is an integer with a value from 1 to 4, preferably m is 1, 2, 3 or 4, more preferably m is 1 or 2.

[0054] As used herein, the term "at least one" includes, but is not limited to, 1, 2, 3, 4, 5, 6, 7, 8, 9 and more.

[0055] Example 2

[0056] The compounds of the present invention, wherein R1 is a C10 to C17 alkyl or a C10 to C17 alkenyl, preferably a C10 to C17 alkyl.

[0057] In a preferred embodiment, R1 is a straight-chain or acyclic branched chain, more preferably a straight-chain R1. Furthermore, R1 is at least C9, at least C10, at least C11, at least C12, at least C13, at least C14, at least C15, at least C16, or at least C17 alkyl or alkenyl, preferably alkyl, and not exceeding C26, not exceeding C25, not exceeding C24, not exceeding C23, not exceeding C22, not exceeding C21, not exceeding C20, not exceeding C19, or not exceeding C18 alkyl or alkenyl, preferably alkyl.

[0058] Example 3

[0059] The compound of the present invention, wherein R2 is Furthermore, the dashed line and M are as defined above, and preferably M is Na or hydrogen, preferably Na.

[0060] Example 4

[0061] The compound of the present invention, wherein

[0062] i)n is an integer with values ​​from 1 to 3; and

[0063] ii) R4 is hydrogen.

[0064] In a preferred embodiment, n is 1, 2, or 3, preferably 1.

[0065] Example 5

[0066] The compounds of the present invention, wherein M is selected from the group consisting of hydrogen, Na, K and ammonia.

[0067] In a preferred embodiment, M is hydrogen or Na.

[0068] In a more preferred embodiment, the compound of the present invention is 2-undecyl-4-hydroxyethyl-1,3-dioxolane according to formula (III) and 2-undecyl-4-ethyl sulfate-1,3-dioxolane sodium salt according to formula (IV):

[0069] (III) and

[0070] (IV).

[0071] Example 6

[0072] In another aspect, the present invention relates to a method for preparing the compound of the present invention, the method comprising:

[0073] i) Make the aldehyde or ketone according to formula (II)

[0074] Equation (II),

[0075] Wherein R3 is a C8 to C27 alkyl or C8 to C27 alkenyl, and

[0076] R4 is hydrogen, a C2 to C18 alkyl group, or a C2 to C18 alkenyl group.

[0077] It reacts with straight-chain triols containing 4 to 12 carbon atoms, wherein the hydroxyl groups are at the 1-, 2-, and ω-positions, in the presence of an acidic catalyst.

[0078] To obtain the compound of the present invention, wherein R2 is And the dashed line is as defined above, and optionally...

[0079] ii) The compound in step i) is sulfated or sulfonated and then neutralized with a base selected from the group consisting of sodium hydroxide or potassium hydroxide, ammonia, amines, and amino alcohols.

[0080] To obtain the compound of the present invention, wherein R2 is or And M, m and the dashed line are as defined above.

[0081] In a preferred embodiment, R3 is a straight-chain or acyclic branched chain, more preferably a straight-chain R3. Furthermore, R3 is at least C9, at least C10, at least C11, at least C12, at least C13, at least C14, at least C15, at least C16, or at least C17 alkyl or alkenyl, preferably alkyl, and not exceeding C26, not exceeding C25, not exceeding C24, not exceeding C23, not exceeding C22, not exceeding C21, not exceeding C20, not exceeding C19, or not exceeding C18 alkyl or alkenyl, preferably alkyl.

[0082] In a preferred embodiment, the linear triol may be selected from the group consisting of: 1,2,4-butanetriol, 1,2,5-pentanetriol, 1,2,6-hexanetriol, 1,2,7-heptanetriol, 1,2,8-octanetriol, 1,2,9-nonanetriol, and 1,2,10-decanetriol, more preferably 1,2,4-butanetriol.

[0083] As used herein, the term "neutralization" refers to raising the pH of the reaction system after sulfation by adding a suitable base. The amount of base will be adjusted so that the final pH is between 5 and 9, and preferably between 6 and 8. Those skilled in the art are well aware of suitable bases.

[0084] In another embodiment, the compounds of the invention are purified (by distillation). Following this purification, the compounds of the invention have a purity level of at least 50%, at least 60%, at least 70%, at least 80%, at least 90%, at least 95%, at least 99%, or at least 99.5% based on a mole fraction (i.e., the amount of the compounds of the invention expressed in moles divided by the total amount of all components in the mixture, also expressed in moles). Specifically, the purification step is performed to separate the compounds of the invention from unreacted substrates, particularly straight-chain triols and aldehydes or ketones.

[0085] In addition, the compounds of the present invention can be further subjected to the following method steps:

[0086] a) Purification using standard methods such as steam distillation, hot distillation, vacuum evaporation (including removal of all solvents), dialysis, and / or

[0087] b) Drying is performed using standard drying methods such as spray drying, drum drying, paddle drying, and vacuum drying. These methods include agglomeration methods such as fluidized bed drying.

[0088] To obtain purified solutions, purified liquids, solids (e.g., granulated or co-granulated) or purified solids, respectively.

[0089] If, after the reaction that produces the compounds of the present invention, the residual substrate is present to an undesirable degree, the resulting mixture of products containing the compounds of the present invention can be further purified by standard means to reduce the content of the residual substrate, as well as the amount of possible byproducts, by reducing the amount of one or more solvents used (i.e., concentration), or by replacing one or more solvents with other solvents. Such methods are known to those skilled in the art.

[0090] Preferably, the unwanted amount of residual substrate is removed by a distillation method, more preferably by a thermal distillation method, which may additionally include applying reduced pressure to improve the rate and / or efficiency of removal.

[0091] In the preferred embodiment, only the additional method step a) is used.

[0092] In another embodiment, the linear triol and aldehyde or ketone are renewable compounds, preferably isolated directly from organisms such as bacteria, algae, fungi, or plants, or prepared from the aforementioned compounds obtained from bacteria, algae, fungi, or plants. In a preferred embodiment, all of the above-mentioned substrates are renewable compounds. The renewable triol may be 1,2,4-butanetriol, which is synthesized using genetically engineered Escherichia coli and Pseudomonas fragi via biotechnology, as described by Cao et al. (Yujin Cao, Wei Niu, Jiantao Guo, MoXian, Huizhou Liu: Biotechnological production of 1,2,4-butanetriol: An efficient process to synthesize energetic material precursor from renewable biomass [1,2,4-Butanetriol Biotechnological Production: An Efficient Method to Synthesize Energetic Material Precursor from Renewable Biomass]. Scientific Reports, Vol. 5, No. 1, 2015, p. 18149).

[0093] Long-chain carboxylic acids are well-known metabolites of bacteria, fungi, or plants. Therefore, these compounds are naturally occurring and renewable. Several different methods have been developed for their isolation, and thus such carboxylic acids are generally commercially available. Furthermore, these carboxylic acids can also be used to produce aldehydes and ketones. Therefore, those skilled in the art also know how to synthesize naturally occurring and renewable aldehydes and ketones.

[0094] Suitable straight-chain triols for preparing the reactions of the present invention are 1,2,4-butanetriol, 1,2,5-pentanetriol, 1,2,6-hexanetriol, 1,2,7-heptanetriol, 1,2,8-octanetriol, 1,2,9-nonanetriol, and 1,2,10-decanetriol, preferably 1,2,4-butanetriol.

[0095] Example 7

[0096] The method of the present invention, wherein the acidic catalyst is selected from the group consisting of alkylbenzene sulfonic acid, methanesulfonic acid, sulfuric acid, phosphoric acid, hypophosphoric acid, and hydrochloric acid.

[0097] In a preferred embodiment, the acid catalyst is an alkylbenzene sulfonic acid according to the formula C10-C13-Ph-SO3H.

[0098] The reaction between a linear triol and an aldehyde or ketone can be carried out at at least 30°C for at least 1 hour. Preferably, the reaction is carried out at a temperature between 40°C and 60°C for 1.5 to 2.5 hours. In a more preferred embodiment, the reaction conditions are 2 hours at 50°C.

[0099] Example 8

[0100] The method of the present invention, wherein

[0101] (i) R3 is a C10 to C17 alkyl or C10 to C17 alkenyl, preferably a C10 to C17 alkyl; and

[0102] (ii) R4 is hydrogen.

[0103] Example 9

[0104] The method of the present invention, wherein the straight-chain triol contains 4 to 6 carbon atoms.

[0105] Example 10

[0106] The method of the present invention, wherein the sulfation step includes

[0107] i) Sulfation with sulfur trioxide in a falling film reactor;

[0108] ii) Sulfate with chlorosulfuric acid; or

[0109] iii) Sulfate with aminosulfonic acid in the presence of urea.

[0110] The sulfur-containing compounds mentioned above have the following chemical structures:

[0111] Sulfur trioxide (SO3), chlorosulfuric acid (ClSO3H), and aminosulfonic acid (H3NSO3).

[0112] In a preferred embodiment, the sulfur trioxide-based sulfation reaction is carried out using a falling film reactor. Such falling film reactors and their use for sulfation (sulfonation) are well known in the art and include falling film reactors from Stepan Corporation (e.g., as described in US 3169142 A) and annular film reactors from Chemithon Corporation (e.g., as described in US 3427342 A).

[0113] Example 11

[0114] The compounds of the present invention are used in cleaning compositions, in fabric and household care products, in cosmetic formulations, as crude oil demulsifiers, as surfactants in enhanced oil recovery, as surfactants in corn oil separation, as surfactants in fermentation processes, as surfactants in mineral ore flotation, in pigment dispersions for inkjet inks, in formulations for electroplating, in adhesive compositions, and as dispersants for agricultural chemical formulations.

[0115] One subject of the present invention is the use of the aforementioned substituted 1,3-dioxolane sulfate in fabric and household care products, in cosmetic formulations, as a crude oil demulsifier, in pigment dispersions for inkjet inks, in formulations for electroplating, in adhesive compositions and / or as a dispersant for agricultural chemical formulations, preferably in cleaning compositions and / or in fabric and household care products, particularly in cleaning compositions for improved clay removal or removal of oily and greasy stains, wherein the cleaning composition is preferably a laundry detergent formulation and / or a hand dishwashing detergent formulation, more preferably a liquid laundry detergent formulation and / or a liquid hand dishwashing detergent formulation.

[0116] The substituted 1,3-dioxolane sulfate can be added to cosmetic formulations, as crude oil demulsifiers, in pigment dispersions for inkjet inks, in formulations for electroplating, and in adhesive compositions. However, the compounds of this invention can also be added to washing or cleaning compositions.

[0117] Therefore, another subject of the present invention is a cleaning composition, fabric and household care product, industrial and institutional cleaning product, cosmetic formulation, crude oil demulsifier, pigment dispersion for inkjet ink, formulation for electroplating, adhesive composition and / or dispersant for agricultural chemical formulation, comprising at least one substituted 1,3-dioxolane sulfate as defined above.

[0118] Preferably, it is a cleaning composition and / or a fabric and household care product (containing at least one substituted 1,3-dioxolane sulfate as defined above, preferably for improved clay removal or oil and grease stain removal), preferably a laundry detergent formulation and / or a detergent formulation for hand dishwashing, more preferably a liquid laundry detergent formulation and / or a liquid detergent formulation for hand dishwashing.

[0119] In another preferred embodiment of the invention, the cleaning composition can be used for the removal of particulate stains and / or oily and greasy stains, and additionally for whiteness maintenance, preferably in laundry care.

[0120] 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, and glass.

[0121] In another embodiment, the cleaning composition of the present invention is a liquid or solid detergent composition for automatic tableware washing, preferably a solid detergent composition for automatic tableware washing, which can be used to clean tableware, such as glassware, wherein the 1,3-dioxolane sulfate substituted by the present invention improves the removal of stubborn dirt.

[0122] In another embodiment, the cleaning composition is designed for use in personal care and pet care compositions such as shampoo compositions, shower gel formulations, liquid or solid soaps.

[0123] In this invention, the preferred application areas for the use of substituted 1,3-dioxolane sulfate are in the fields of fabric and home care products and cleaning compositions, preferably for cleaning compositions for industrial and institutional use, and for consumer use in their homes.

[0124] Example 12

[0125] The invention is used in cleaning compositions and / or in fabric and household care products, preferably in cleaning compositions.

[0126] i) Improved removal of oily / greasy stains, and / or

[0127] ii) Improved sebum removal, and / or

[0128] iii) Clay removal, and / or

[0129] iv) Removal of particulate stains, and / or

[0130] v) Dispersion and / or emulsification of dirt, and / or

[0131] vi) Modification of the treated surface to improve the removal of subsequent contamination, and / or

[0132] vii) Whiteness improvement and / or

[0133] Preferably used in cleaning compositions for the removal of oily / greasy stains.

[0134] Each of the preceding options i) to vii) is preferably used in laundry detergent formulations and / or detergent formulations for hand-washing dishes and / or formulations suitable for (pre)treating textiles and / or soap bars, more preferably in liquid laundry detergent formulations and / or liquid detergent formulations for hand-washing dishes.

[0135] Example 13

[0136] Cleaning compositions, fabric and household care products, industrial and institutional cleaning products, cosmetic formulations, crude oil demulsifiers, oil recovery formulations, formulations for corn oil separation, formulations for fermentation processes, flotation agents for mineral ores, pigment dispersions for inkjet inks, formulations for electroplating, adhesive compositions, dispersants for agricultural chemical formulations, comprising at least one compound according to any one of claims 1 to 5, preferably cleaning compositions and / or fabric and household care products and / or industrial and institutional cleaning products comprising at least one compound of the present invention.

[0137] Example 14

[0138] The cleaning composition of the present invention further comprises

[0139] i) at least one cleaning polymer or stain-removing polymer, and / or

[0140] ii) at least one additional surfactant selected from the group consisting of anionic surfactants and / or nonionic surfactants and / or amphoteric surfactants and / or amphoteric surfactants and / or cationic surfactants, and / or

[0141] iii) An antimicrobial agent selected from the group consisting of 2-phenoxyethanol and 4,4'-dichloro-2-hydroxydiphenyl ether; preferably comprising 2-phenoxyethanol in an amount ranging from 2 ppm to 5% by weight of the composition; more preferably comprising 0.1% to 2% phenoxyethanol or preferably comprising 0.001% to 3%, more preferably 0.002% to 1%, or even more preferably 0.01% to 0.6% of 4,4'-dichloro-2-hydroxydiphenyl ether, each by weight of the composition, and / or

[0142] iv) At least one enzyme selected from the list consisting of lipases, hydrolases, amylases, DNases, proteases, cellulases, hemicellulases, phospholipases, esterases, mannanases, xylanases, dispersases, oxidoreductases, cutinases, pectinases, pectinases, lactases, and peroxidases, and combinations of at least two of the foregoing types, preferably selected from one or more lipases, hydrolases, amylases, proteases, cellulases, and combinations of at least two of the foregoing types, more preferably at least one enzyme selected from proteases, and / or

[0143] v) At least one compound selected from the group consisting of detergent builders, co-builders, structuring agents or thickeners, clay stain removers / anti-redeposition agents, polymer detergents, dispersants such as polymer dispersants, polymer grease cleaners, solubilizers, chelating agents, enzymes, enzyme stabilizers, bleaching compounds, bleaching agents, bleaching activators, bleaching catalysts, brighteners, odor control agents, pigments, dyes, opacifiers, colorants, dye transfer inhibitors, chelating agents, foaming agents, foam inhibitors (defoamers), color speckles, silver care agents, anti-discoloration agents and / or preservatives, alkalinity sources, pH adjusters, pH buffers, water-soluble additives, detergent particles, antibacterial agents, antioxidants, softeners, carriers, processing aids, fragrance precursors, dye fixatives, and fragrances.

[0144] vi) A cosolvent selected from the group consisting of aliphatic alcohols, diols (preferably propylene glycol), or triols containing 2 to 5 carbon atoms, or from the group consisting of ethylene glycol or diethylene glycol monoalkyl ethers containing 2 to 5 carbon atoms in the alkyl portion, or from the group consisting of propylene glycol or dipropylene glycol monoalkyl ethers containing 2 to 5 carbon atoms in the alkyl portion, and / or

[0145] vii) Water.

[0146] Example 15

[0147] A cleaning method comprising bringing the cleaning composition of the present invention into contact with an object, preferably clothing or hard-surface household item, that needs to be cleaned.

[0148] As used herein, the term "cleaning" refers to any act of removing dirt, bleaching, reducing microbial communities, or a combination thereof. This includes washing fabrics by hand with water using a washing machine, an automatic dishwashing machine, or by hand rinsing the fabric with water or washing it with the liquid cleaning composition of the present invention. Preferably, cleaning is performed at a temperature of 60°C or lower, more preferably at 40°C or lower, and most preferably at 30°C or lower. In other preferred embodiments, the cleaning method is performed under water-saving conditions. This means that no more than 60%, 70%, 80%, 90%, or 95% of the water generally recommended for a given cleaning procedure is used in the cleaning method of the present invention.

[0149] The following examples are intended to further illustrate the invention but do not limit its scope.

[0150] This invention encompasses the specific embodiments described throughout this disclosure as part of the invention; various additional options are disclosed in the specification as “optional,” “preferred,” “more preferred,” “even more preferred,” or “most preferred” (or “preferred,” etc.), and options of specific embodiments may be selected individually and independently (unless such independent selection is impossible due to the nature of the feature or if such independent selection is explicitly excluded) and then combined with any other embodiment (where other such options and preferences may also be selected individually and independently, unless such independent selection is impossible due to the nature of the feature or if such independent selection is explicitly excluded), wherein each and any and all such possible combinations are included as separate embodiments as part of the invention.

[0151] As used herein, when used in the claims or embodiments, the articles “a” and “an” should be understood to mean one or more of the claimed or described. As used herein, the terms “include” and “including” are non-limiting and therefore cover more than the specific entries mentioned after these words.

[0152] The compositions disclosed herein may “comprise” (i.e. contain other ingredients) the components disclosed herein, “consistently comprised of the components disclosed herein” (mainly or almost entirely comprised of the mentioned ingredients and only in very small amounts of other ingredients, mainly as impurities), or “composed of the components disclosed herein” (i.e. contain only the mentioned ingredients and may additionally contain only impurities unavoidable in the technical environment, preferably only those ingredients).

[0153] As used herein, the term "at least one" includes, but is not limited to, 1, 2, 3, 4, 5, 6, 7, 8, 9 and more.

[0154] Similarly, the terms “substantially free of …”, “substantially free from …”, or “(containing / comprising) essentially no …” may be used herein; this means that the indicated material is present in a very small amount unintentionally added to the composition to form a part of it, or, preferably, not at an analytically detectable level. It means a composition comprising the indicated material only as an impurity in one of the other intentionally included materials. If present, the indicated material may be present at a level of less than 1%, or even less than 0.1%, or even much less than 0.01%, or even 0% by weight of the composition.

[0155] As used herein, the term "about" encompasses the exact number "X" referred to as, for example, "about X%", as well as small variations of X, including deviations from X by -5% to +5% (where X is set to 100% for such calculations), preferably -2% to +2%, more preferably -1% to +1%, even more preferably -0.5% to +0.5%, and smaller variations. Of course, if the given value X is already "100%" (e.g., for purity), then the term "about" can explicitly and indeed truly refer only to a deviation less than "100".

[0156] Unless otherwise stated, all component or composition levels refer to the active portion of the component or composition and do not include impurities that may be present in commercially available sources of such components or compositions, such as residual solvents or byproducts.

[0157] Unless otherwise indicated, all temperatures herein are in degrees Celsius (°C). Unless otherwise stated, all measurements herein were performed at 20°C and atmospheric pressure. In all embodiments disclosed herein, unless otherwise specified, all percentages are by weight of the total composition. Unless otherwise specified, all ratios are by weight.

[0158] Description of cleaning compositions, formulations and their ingredients

[0159] As used herein, the phrase "cleaning composition" includes compositions and formulations designed for cleaning soiled materials. Such compositions and formulations include those designed for cleaning any kind of soiled material or surface.

[0160] Compositions for “industrial and institutional cleaning” include cleaning compositions designed for use in industrial and institutional cleaning, such as cleaning compositions for cleaning any kind of soiled materials or surfaces, such as hard surface cleaners for any kind of surfaces (including tile, carpet, PVC-coated surfaces, wood surfaces, metal surfaces, and painted surfaces).

[0161] "Compositions for fabric and household care" include cleaning compositions and formulations, including but not limited to laundry cleaning compositions and detergents, fabric softening compositions, fabric reinforcing compositions, fabric cleaning compositions, laundry pre-wash agents, laundry pretreatment agents, laundry additives, spray products, drying cleaning agents or compositions, laundry rinsing additives, washing additives, post-rinse fabric treatment agents, ironing aids, dishwashing compositions, hard surface cleaning compositions, unit-dose formulations, delayed-delivery formulations, detergents contained on or in porous substrates or nonwoven sheets, and other suitable forms that will be apparent to those skilled in the art in light of the teachings herein and are detailed below in the description of the compositions. Such compositions can be used as pre-wash treatment agents, post-wash treatment agents, or can be added during the rinsing or washing cycle of a laundry operation, preferably during the washing cycle of a laundry or dishwashing operation, and are further detailed below in the description of the uses and applications of the compounds of the invention and compositions comprising such polymers.

[0162] The cleaning compositions of the present invention can be in any form, i.e., in the following forms: liquid; solid, such as powder, granules, agglomerates, pastes, tablets, sachets, sticks, gels; emulsions; delivered in dual-compartment or multi-compartment containers; single-phase or multi-phase unit doses; spray or foam detergents; pre-wet wipes (i.e., cleaning compositions combined with nonwoven materials, such as those discussed in US 6,121,165, Mackey et al.); dry wipes (i.e., cleaning compositions combined with nonwoven materials, such as those discussed in US 5,980,931, Fowler et al.), which are activated by water by the user or consumer; and other homogeneous, non-homogeneous, or single-phase or multi-phase cleaning product forms.

[0163] The liquid cleaning composition of the present invention preferably has a strength of 50 to 10000 mPa. The viscosity of the liquid manual dishwashing composition (also known as the liquid manual "dishwashing composition") is preferably 100 to 10000 mPa at 20 1 / s and 20°C. s, more preferably 200 to 5000 mPa s and most preferably 500 to 3000 mPa The viscosity of the liquid laundry cleaning composition is preferably 50 to 3000 mPa at 20 1 / s and 20°C. s, more preferably 100 to 1500 mPa s and most preferably 200 to 1000 mPa The viscosity of s.

[0164] The liquid cleaning composition of the present invention can have any suitable pH value. Preferably, the pH of the composition is adjusted to between 4 and 14. More preferably, the composition has a pH of 6 to 13, even more preferably 6 to 10, and most preferably 7 to 9. The pH of the composition can be adjusted using pH-modifying agents known in the art and measured at 25°C in demineralized water at a 10% product concentration. For example, NaOH can be used, and the actual weight percentage of NaOH can be varied and adjusted to a desired pH such as pH 8.0. In one embodiment of the invention, the pH is adjusted to > 7 by using an amine, preferably an alkanolamine, more preferably triethanolamine.

[0165] Cleaning compositions, such as fabric and household care products and formulations for industrial and institutional cleaning, more specifically such as laundry detergents and hand dishwashing detergents, are known to those skilled in the art. Any compositions known to those skilled in the art, etc. (in conjunction with their respective uses), can be used in the context of this invention by comprising at least one compound of the invention, preferably at least one polymer, in an amount suitable for exhibiting certain properties in such compositions (especially when such compositions are used in their field of application).

[0166] Another aspect of the invention is the use of the compounds of the invention as additives for detergent formulations, particularly for liquid detergent formulations, preferably concentrated liquid detergent formulations, or for single-use, single-dose additives for laundry.

[0167] The cleaning compositions of the present invention may—and preferably certainly do—contain auxiliary cleaning additives (also referred to herein as “auxiliaries”), which are preferably in addition to surfactant systems as previously defined.

[0168] Suitable auxiliary cleaning additives include detergent builders, co-detergent builders, structuring agents or thickeners, clay stain removers / anti-redeposition agents, polymer detergents, dispersants such as polymer dispersants, polymer grease cleaners, solubilizers, chelating agents, enzymes, enzyme stabilizers, bleaching compounds, bleaching agents, bleaching activators, bleaching catalysts, brighteners, odor control agents, pigments, dyes, opacifiers, toners, dye transfer inhibitors, chelating agents, foaming agents, foam inhibitors (defoamers), stain removers, silver care agents, anti-tarnish agents and / or preservatives, alkalinity sources, pH adjusters, pH buffers, water-soluble additives, detergent granules, antibacterial agents, antioxidants, softeners, carriers, processing aids, fragrance precursors, dye fixatives, and fragrances.

[0169] The liquid cleaning composition may additionally include—and preferably does include—at least one of a rheology control agent / modifier, emollient, humectant, skin rejuvenating active, and solvent.

[0170] The solid composition may additionally include—and preferably does include—at least one of filler, bleach, bleach activator, and catalytic material.

[0171] Suitable examples and levels of use of such cleaning aids can be found in WO 99 / 05242, U.S. Patent Nos. 5,576,282, 6,306,812 B1 and 6,326,348 B1.

[0172] Those skilled in the art will understand that detergency surfactants encompass any surfactant or mixture of surfactants that provides cleaning, stain removal, or washing benefits to soiled materials.

[0173] Therefore, the cleaning compositions of the present invention, such as fabric and household care products, as well as formulations for industrial and institutional cleaning, more specifically such as laundry detergents and hand dishwashing detergents, preferably additionally contain a surfactant system, and more preferably additional adjuvants, such as those described above and below in more detail.

[0174] A surfactant system may consist of a single surfactant or a combination of surfactants selected from anionic surfactants, nonionic surfactants, cationic surfactants, amphoteric surfactants, amphoteric surfactants, and mixtures thereof. Those skilled in the art will understand that surfactant systems for detergents encompass any surfactant or mixture of surfactants that provides cleaning, stain removal, or washing benefits to soiled materials.

[0175] The cleaning compositions of the present invention preferably comprise a surfactant system in an amount sufficient to provide the desired cleaning properties. In some embodiments, the cleaning composition comprises about 1% to about 70% of the surfactant system by weight of the composition. In other embodiments, the liquid cleaning composition comprises about 2% to about 60% of the surfactant system by weight of the composition. In still other embodiments, the cleaning composition comprises about 5% to about 30% of the surfactant system by weight of the composition. The surfactant system may comprise detergency surfactants selected from anionic surfactants, nonionic surfactants, cationic surfactants, amphoteric surfactants, amphoteric surfactants, and mixtures thereof.

[0176] (a) Laundry composition

[0177] In laundry products, anionic surfactants typically constitute the largest proportion of the surfactants used. Therefore, preferably, the cleaning compositions of the present invention for washing clothes comprise at least one anionic surfactant and optionally additional surfactants selected from any of the surfactant classes described herein, preferably from nonionic surfactants and / or amphoteric surfactants and / or amphoteric surfactants and / or cationic surfactants other than the surfactants of the present invention.

[0178] Non-limiting examples of anionic surfactants available in this article—which may also be used in combination with more than one surfactant—include C9-C. 20 Linear alkylbenzene sulfonates (LAS), C 10 -C 20 Primary, branched and random alkyl sulfates (AS); C 10 -C 18 secondary (2,3)alkyl sulfates; C 10 -C 18 Alkylalkoxy sulfates (AExS), where x is 1 to 30; C containing 1 to 5 ethoxy units. 10 -C 18 Alkyl alkoxycarboxylates; medium-chain branched alkyl sulfates, as discussed in US 6,020,303 and US 6,060,443; medium-chain branched alkyl alkoxy sulfates, as discussed in US 6,008,181 and US 6,020,303; modified alkylbenzene sulfonates (MLAS), as discussed in WO 99 / 05243, WO 99 / 05242 and WO 99 / 05244; methyl ester sulfonates (MES); and α-olefin sulfonates (AOS).

[0179] Preferred examples of suitable anionic surfactants are the following alkali metal salts and ammonium salts: C8-C 12 -Alkyl sulfate, C 12 -C 18 - Fatty alcohol ether sulfate, C 12 -C 18 - Fatty alcohol polyether sulfate, ethoxylated C4-C 12 -Alkylphenol sulfate half-ester (ethoxylation: 3 to 50 mol ethylene oxide / mol), C 12 -C 18 -Alkyl sulfonic acid, C 12 -C 18 sulfonyl fatty acid alkyl esters, such as C 12 -C 18 sulfonyl fatty acid methyl ester, C 10 -C 18 -alkylarylsulfonic acid, preferably C10 -C 18 -alkylbenzene sulfonic acid, C 10 -C 18 Alkyl alkoxycarboxylic esters and soaps, such as C8-C 24 -Carboxylic acid. Preferably, it is an alkali metal salt of the aforementioned compound, and particularly preferably a sodium salt.

[0180] In one embodiment of the present invention, the anionic surfactant is selected from C-type surfactants. 10 -C 18 - Alkylbenzene sulfonic acid and fatty alcohol polyether sulfate, in the context of this invention, particularly ethoxylated C 12 -C 18 -Alkyl alcohol (preferably C-1) 12 -C 18 Half-esters of alkyl alcohols (ethoxylated: 1 to 50 mol of ethylene oxide / mol).

[0181] In one embodiment of the invention, C derived from branched chains (i.e., synthetically produced) can also be used. 11 -C 18 - Alkyl alcohol polyether sulfate (ethoxylation: 1 to 50 mol ethylene oxide / mol).

[0182] Preferably, based on C 12 -C 18 - Fatty alcohols or branched (i.e. synthetic) C 11 -C 18 The alkoxylation group of the two types of alkoxylated alkyl sulfates of alcohols is an ethoxylation group, and the average degree of ethoxylation of any alkoxylated alkyl sulfate is 1 to 5, preferably 1 to 3.

[0183] In another embodiment of the invention, the anionic surfactant is selected from rhamnolipid and / or sophorolipid.

[0184] Preferably, the laundry detergent formulation of the present invention comprises at least 1 wt.% to 50 wt.% of, preferably in the range of greater than or equal to about 2 wt.% to equal to or less than about 30 wt.%, more preferably in the range of greater than or equal to 3 wt.% to equal to or less than 25 wt.%, and most preferably in the range of greater than or equal to 5 wt.% to equal to or less than 25 wt.%, based on a specific overall composition (containing other components and water and / or solvent), one or more of the anionic surfactants described above.

[0185] In a preferred embodiment of the present invention, the anionic surfactant is selected from C 10 -C 15 Straight-chain alkylbenzene sulfonates, C with 1-5 ethoxy units 10 -C18 Alkyl ether sulfates and C 10 -C 18 Alkyl sulfates.

[0186] Non-limiting examples of nonionic surfactants—which may also be used in combination with more than one other surfactant—include: C8-C 18 Alkyl ethoxylates, such as NEODOL® nonionic surfactants from Shell; and ethylene oxide / propylene oxide block alkoxylates from BASF's PLURONIC®; C 14 -C 22 Medium-chain branched alkyl alkoxylates BAEx, wherein x is 1 to 30, as discussed in US 6,153,577, US 6,020,303 and US 6,093,856; alkyl polysaccharides, as discussed in US 4,565,647, published January 26, 1986 in Llenado; specifically, alkyl polyglycosides, as discussed in US 4,483,780 and US 4,483,779; polyhydroxy fatty acid amides, as discussed in US 5,332,528; and ether-terminated poly(oxyalkylated) alcohol surfactants, as discussed in US 6,482,994 and WO 01 / 42408.

[0187] Preferred examples of nonionic surfactants include, in particular, alkoxylated alcohols and alkoxylated fatty alcohols, diblock and multiblock copolymers of ethylene oxide and propylene oxide, and reaction products of sorbitol with ethylene oxide or propylene oxide, as well as alkylphenol ethoxylates, alkyl glycosides, and polyhydroxy fatty acid amides (glucosamides).

[0188] Preferred examples of alkoxylated alcohols and alkoxylated fatty alcohols are, for example, compounds having the general formula (A).

[0189] [Formula (A)]

[0190] The variables are defined as follows:

[0191] R 1 Selected from linear C1-C 10 -alkyl, preferably ethyl and particularly preferably methyl,

[0192] R 2 Selected from C8-C 22 -alkyl, for example, C8H 17 C 10 H 21 C 12 H 25 C 14 H29 C 16 H 33 or positive C 18 H 37 ,

[0193] R 3 Selected from C1-C 10 -alkyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, neopentyl, 1,2-dimethylpropyl, isopentyl, n-hexyl, isohexyl, sec-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl or isodel,

[0194] m and n are in the range of 0 to 300, wherein the sum of n and m is at least one. Preferably, m is in the range of 1 to 100 and n is in the range of 0 to 30.

[0195] Here, the compound having the general formula (A) can be a block copolymer or a random copolymer, preferably a block copolymer.

[0196] Other preferred examples of alkoxylated alcohols and alkoxylated fatty alcohols are, for example, compounds having the general formula (B).

[0197] [Formula (B)]

[0198] The variables are defined as follows:

[0199] R 1 They may be the same or different and are selected from straight-chain C1-C4-alkyl groups, preferably the same in each case and ethyl, and particularly preferably methyl.

[0200] R 4 Selected from C6-C 20 -alkyl groups, especially C8H 17 C 10 H 21 C 12 H 25 C 14 H 29 C 16 H 33 C 18 H 37 ,

[0201] a is a number in the range of zero to 6, preferably 1 to 6.

[0202] b is a number in the range of zero to 20, preferably 4 to 20.

[0203] d is a number in the range of 4 to 25.

[0204] Preferably, at least one of a and b is greater than zero.

[0205] Here, the compound having general formula (B) can be a block copolymer or a random copolymer, preferably a block copolymer.

[0206] Other suitable nonionic surfactants are selected from diblock and multiblock copolymers of ethylene oxide and propylene oxide. Other suitable nonionic surfactants are selected from ethoxylated or propoxylated sorbitol esters. Alkylphenol ethoxylates, alkyl polyglycosides, or polyhydroxy fatty acid amides (glucosamides) are also suitable. An overview of suitable other nonionic surfactants can be found in EP A 0 851 023 and DE-A 198 19 187.

[0207] Of course, a mixture of two or more different nonionic surfactants can also exist.

[0208] In a preferred embodiment of the present invention, the nonionic surfactant is selected from C 12 / 14 and C 16 / 18 Fatty alcohol alkoxylates, C 13 / 15 Oxy-ol alkoxylates, C 13 - Alcohol alkoxylates and 2-propylheptyl alcohol alkoxylates, each having 3-15 ethoxy units, preferably 4-10 ethoxy units, or having 1-3 propoxy units and 2-15 ethoxy units.

[0209] Non-limiting examples of amphoteric surfactants—which may also be used in combination with more than one other surfactant—include: a water-soluble amine oxide comprising an alkyl moiety having about 8 to about 18 carbon atoms and two portions selected from the group consisting of an alkyl moiety having about 1 to about 3 carbon atoms and a hydroxyalkyl moiety; and a water-soluble sulfoxide comprising an alkyl moiety having about 10 to about 18 carbon atoms and a portion selected from the group consisting of an alkyl moiety having about 1 to about 3 carbon atoms and a hydroxyalkyl moiety. See WO 01 / 32816, US 4,681,704 and US 4,133,779. Thus, suitable surfactants include so-called amine oxides, such as lauryl dimethylamine oxide (“laurylamine oxide”).

[0210] Preferred examples of amphoteric surfactants are amine oxides. Preferred amine oxides are alkyl dimethylamine oxides or alkylamidopropyl dimethylamine oxides, more preferably alkyl dimethylamine oxides, and especially cocoyl dimethylamine oxides. Amine oxides may have a straight-chain or intermediate-branched alkyl moiety. Typical straight-chain amine oxides include water-soluble amine oxides containing an R... 1= C 8-18 The alkyl moiety and the two Rs selected from the group consisting of C1-C3 alkyl and C1-C3 hydroxyalkyl. 2 and R 3 Partially. Preferably, the amine oxide is characterized by the following formula.

[0211] R 1 -N(R 2 (R) 3 )-O

[0212] Where R 1 It is C8- 18 Alkyl and R 2 and R 3 Selected from the group consisting of: methyl, ethyl, propyl, isopropyl, 2-hydroxyethyl, 2-hydroxypropyl, and 3-hydroxypropyl. Straight-chain amine oxide surfactants may in particular include straight-chain C... 10 -C 18 Alkyl dimethylamine oxides and straight-chain C8-C 12 Alkoxyethyl dihydroxyethyl amine oxide. Preferred amine oxides include straight-chain C... 10 Straight-chain C 10 -C 12 and straight chain C 12 -C 14 Alkyl dimethylamine oxide. As used herein, “intermediate branch” means an amine oxide having an alkyl moiety having n1 carbon atoms, wherein an alkyl branch is present on the alkyl moiety having n2 carbon atoms. The alkyl branch is located on the α-carbon of nitrogen from the alkyl moiety. This type of branching of amine oxides is also referred to in the art as internal amine oxides. The sum of n1 and n2 is 10 to 24, preferably 12 to 20, and more preferably 10 to 16 carbon atoms. The number of carbon atoms (n1) of the alkyl moiety should be approximately the same as the number of carbon atoms (n2) of the alkyl branch, such that the alkyl moiety and the alkyl branch are symmetrical. As used herein, “symmetrical” means that in at least 50 wt.%, more preferably at least 75 wt.% to 100 wt.% of the intermediate branch amine oxides used herein, (n1-n2) is less than or equal to 5, preferably 4, and most preferably 0 to 4 carbon atoms. The amine oxide further comprises two moieties, each independently selected from C1-C3 alkyl, C1-C3 hydroxyalkyl, or polyoxyethylene alkyl groups containing an average of about 1 to about 3 ethylene oxide groups. Preferably, the two moieties are selected from C1-C3 alkyl, more preferably both are selected from C1 alkyl.

[0213] In a preferred embodiment of the present invention, the amphoteric surfactant is selected from C8-C. 18 Alkyl-dimethylamine oxides and C8-C 18Alkyl-di(hydroxyethyl)amine oxide.

[0214] The cleaning composition may also contain amphoteric surfactants – which may also be used in combination with more than one other surfactant.

[0215] Suitable amphoteric surfactants include betaines, such as alkyl betaines, alkylamidobetaines, imidazolinium betaines, sulfobetaine (INCI sulfobetaine), and phosphate betaines. Examples of suitable betaines and sulfobetaines are as follows (according to INCI nomenclature): Almond amidopropyl betaine, Apricotamidopropyl betaine, Avocadoamidopropyl betaine, Babassuamidopropyl betaine, Behenamidopropyl betaine, Behenyl betaine, Low-erucic acid amidopropyl betaine, Capryloyl / Decanamidopropyl betaine, Carnitine, Cetyl betaine, Cocamidoethyl betaine, Cocamidopropyl ... Aminopropylhydroxysulfonyl betaine, cocobetaine, cocobetaine hydroxysulfonyl betaine, coco / oleamidopropyl betaine, cocobetaine sulfonyl betaine, decyl betaine, oleylglycine dihydroxyethyl ester, daidzeinylglycine dihydroxyethyl ester, stearylglycine dihydroxyethyl ester, tallow glycine dihydroxyethyl ester, polydimethylsiloxanepropyl PG-betaine, erucamide propylhydroxysulfonyl betaine, hydrogenated tallow betaine, isostearamide propyl betaine, Laurylamidopropyl betaine, lauryl betaine, lauryl hydroxysulfonyl betaine, lauryl sulfonyl betaine, milk amamidopropyl betaine, mink oil amamidopropyl betaine, myristoyl amamidopropyl betaine, myristyl betaine, oleamidopropyl betaine, oleamidopropyl hydroxysulfonyl betaine, oil-based betaine, olive oil amamidopropyl betaine, palm oil amamidopropyl betaine, palmitoyl carnitine Palm kernel oleamidopropyl betaine, polytetrafluoroethylene acetoxypropyl betaine, castor oil oleamidopropyl betaine, sesame oil oleamidopropyl betaine, soybean oil oleamidopropyl betaine, stearamidopropyl betaine, stearyl betaine, butteramidopropyl betaine, butteramidopropyl hydroxysulfonyl betaine, butter betaine, butter dihydroxyethyl betaine, undecenoylamidopropyl betaine, and wheat germ oleamidopropyl betaine.

[0216] Preferred betaine is, for example, C 12 -C 18 -Alkyl betaine and sulfobetaine. The zwitterionic surfactant is preferably a betaine surfactant, and more preferably a cocamidopropyl betaine surfactant.

[0217] Non-limiting examples of cationic surfactants—which may also be used in combination with more than one other surfactant—include: quaternary ammonium surfactants, which may have up to 26 carbon atoms, including: alkoxylated quaternary ammonium (AQA) surfactants as discussed in US 6,136,769; dimethylhydroxyethyl quaternary ammonium as discussed in US 6,004,922; dimethylhydroxyethyl lauryl ammonium chloride; polyamine cationic surfactants as discussed in WO 98 / 35002, WO 98 / 35003, WO 98 / 35004, WO 98 / 35005, and WO98 / 35006; cationic ester surfactants as discussed in US Patent Nos. 4,228,042, 4,239,660, 4,260,529, and US 6,022,844; and cationic ester surfactants as discussed in US 6,221,825 and WO The amino surfactant discussed in 00 / 47708 is specifically amamidopropyl dimethylamine (APA).

[0218] The compositions according to the invention may contain at least one builder. In the context of this invention, no distinction will be made between a builder and such components elsewhere referred to as "co-builders". Examples of builders are complexing agents, also referred to hereinafter as complexing agents, ion exchange compounds, and precipitants. Builders are selected from citrates, phosphates, silicates, carbonates, phosphonates, aminocarboxylates, and polycarboxylates.

[0219] In the context of this invention, the term citrate includes monoalkali metal salts and dialkali metal salts of citrate, and particularly monosodium salts and preferably trisodium salts of citrate, ammonium salts or substituted ammonium salts of citrate, and citrate itself. Citrates can be used as anhydrous compounds or as hydrates, for example as sodium citrate dihydrate. The amount of citrate is calculated with reference to anhydrous trisodium citrate.

[0220] The term phosphate includes sodium metaphosphate, sodium orthophosphate, sodium hydrogen phosphate, sodium pyrophosphate, and polyphosphates such as sodium tripolyphosphate. However, preferably, the compositions according to the invention are free of phosphates and polyphosphates, wherein hydrogen phosphate is included, for example, free of trisodium phosphate, pentasodium tripolyphosphate, and hexasodium metaphosphate (“phosphate-free”). In the context of this invention, “phosphate-free” should be understood to mean that the total content of phosphates and polyphosphates is in the range of 10 ppm to 0.2% by weight of the respective composition, determined by gravimetric analysis.

[0221] The term "carbonate" includes alkali metal carbonates and alkali metal bicarbonates, with sodium salts being preferred. Na₂CO₃ is particularly preferred.

[0222] Examples of phosphonates are hydroxyalkylphosphonates and aminoalkylphosphonates. Among hydroxyalkylphosphonates, 1-hydroxyethane-1,1-diphosphonate (HEDP) is particularly important as a detergent builder. It is preferably used as a sodium salt, with the disodium salt being neutral and the tetrasodium salt being alkaline (pH 9). Suitable aminoalkylphosphonates are preferably ethylenediaminetetramethylenephosphonate (EDTMP), diethylenetriaminepentamethylenephosphonate (DTPMP), and their higher homologues. They are preferably used in the form of neutral reactive sodium salts, such as the hexasodium salt of EDTMP or the heptasodium and octasodium salts of DTPMP.

[0223] Examples of aminocarboxylates and polycarboxylates are hypotriacetate, ethylenediaminetetraacetate, diethylenetriaminepentaacetate, triethylenetetraaminehexaacetate, propylenediaminetetraacetate, ethanol-diglycine salt, methylglycine diacetate, and glutamine diacetate. The terms aminocarboxylates and polycarboxylates also include their respective unsubstituted or substituted ammonium salts and alkali metal salts, such as sodium salts, particularly sodium salts of their respective completely neutralized compounds.

[0224] In the context of this invention, silicates particularly include sodium disilicate and sodium metasilicate, aluminosilicates such as zeolites and layered silicates, especially those having the formulas α-Na2Si2O5, β-Na2Si2O5, and δ-Na2Si2O5.

[0225] The compositions according to the invention may contain one or more detergent builders selected from materials not mentioned above. Examples of detergent builders are α-hydroxypropionic acid and oxidized starch.

[0226] In one embodiment of the invention, the detergent builder is selected from polycarboxylate salts. The term "polycarboxylate salt" includes non-polymerized polycarboxylate salts, such as succinic acid, C2-C... 16 -alkyl disuccinate, C2-C 16 -Alkenyl disuccinate, ethylenediamine N,N'-disuccinic acid, tartaric acid diacetate, alkali metal malonate, tartaric acid monoacetate, propane tricarboxylic acid, butane tetracarboxylic acid and cyclopentane tetracarboxylic acid.

[0227] Oligomeric or polymeric polycarboxylic acids are, for example, alkali metal salts of polyaspartic acid or, in particular, homopolymers or copolymers of (meth)acrylic acid.

[0228] Suitable comonomers are monoolefinically unsaturated dicarboxylic acids, such as maleic acid, fumaric acid, maleic anhydride, itaconic acid, and citraconic acid. Suitable polymers are particularly polyacrylic acid, preferably having a weight-average molecular weight (Mw) in the range of 2000 to 40,000 g / mol, preferably 2000 to 10,000 g / mol, and particularly 3000 to 8000 g / mol. Further suitable comonomers are, in particular, those of acrylic acid and methacrylic acid, and those of acrylic acid or methacrylic acid and maleic acid and / or fumaric acid.

[0229] Alternatively, at least one type of monoene-bonded unsaturated C3-C can be used. 10 -Single- or C4-C 10 A copolymer of monomers of the group consisting of dicarboxylic acids or their anhydrides (such as maleic acid, maleic anhydride, acrylic acid, methacrylic acid, fumaric acid, itaconic acid and citraconic acid) with at least one hydrophilic or hydrophobic modified comonomer listed below.

[0230] Suitable hydrophobic comonomers are, for example, isobutylene, diisobutylene, butene, pentene, hexene, and styrene; olefins having ten or more carbon atoms, or mixtures thereof, such as, for example, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, 1-eicosene, 1-docodecene, 1-tetradecene, and 1-hexadecene, C 22 -α-olefin, C 20 -C 24 A mixture of -α-olefins and polyisobutylene having an average of 12 to 100 carbon atoms / molecule.

[0231] Suitable hydrophilic comonomers are monomers having sulfonate or phosphonate groups, as well as nonionic monomers having hydroxyl or epoxyalkyl groups. Examples include: allyl alcohol, isoprene alcohol, methoxy polyethylene glycol (meth)acrylate, methoxy polypropylene glycol (meth)acrylate, methoxy polybutylene glycol (meth)acrylate, methoxy poly(propylene oxide-copolymer-ethylene oxide) (meth)acrylate, ethoxy polyethylene glycol (meth)acrylate, ethoxy polypropylene glycol (meth)acrylate, ethoxy polybutylene glycol (meth)acrylate, and ethoxy poly(propylene oxide-copolymer-ethylene oxide) (meth)acrylate. The polyalkylene glycol may contain 3 to 50, particularly 5 to 40, and especially 10 to 30 epoxyalkyl units / molecules.

[0232] Particularly preferred monomers containing sulfonic acid groups are 1-acrylamido-1-propanesulfonic acid, 2-acrylamido-2-propanesulfonic acid, 2-acrylamido-2-methylpropanesulfonic acid, 2-methacrylamido-2-methylpropanesulfonic acid, 3-methacrylamido-2-hydroxypropanesulfonic acid, allylsulfonic acid, methylallylsulfonic acid, allyloxybenzenesulfonic acid, methylallyloxybenzenesulfonic acid, 2-hydroxy-3-(2-acryloxy)propanesulfonic acid, 2-methyl-2-propene-1-sulfonic acid, styrenesulfonic acid, vinylsulfonic acid, 3-sulfopropyl acrylate, 2-sulfoethyl methacrylate, 3-sulfopropyl methacrylate, sulfomethylacrylamide, sulfomethylmethylacrylamide, and salts of said acids, such as their sodium, potassium, or ammonium salts.

[0233] The preferred monomers containing phosphonate groups are vinylphosphonic acid and its salts.

[0234] In addition, amphoteric polymers can also be used as detergent builders.

[0235] The compositions according to the invention may contain, for example, one or more builder agents in total of 0.1% to 70% by weight, preferably 10% to 50% by weight, and preferably up to 20% by weight, especially in the case of solid formulations. Liquid formulations according to the invention preferably contain builder agents in the range of 0.1% to 8% by weight.

[0236] The formulations according to the invention may contain one or more basic carriers. For example, if an alkaline pH is desired, the basic carrier ensures a pH of at least 9. Suitable carriers include, for example, the aforementioned alkali metal carbonates, alkali metal bicarbonates, and alkali metal metasilicates, and additionally, alkali metal hydroxides. In each case, the preferred alkali metal is potassium, and particularly preferred is sodium. In one embodiment of the invention, the pH is adjusted to > 7 by using an amine, preferably an alkanolamine, more preferably triethanolamine.

[0237] In one embodiment of the invention, the composition or laundry preparation according to the invention additionally contains at least one enzyme.

[0238] In one embodiment, the composition according to the invention additionally contains at least one enzyme.

[0239] Preferably, the at least one enzyme is a detergent enzyme.

[0240] In one embodiment, the enzyme is classified as an oxidoreductase (EC 1), transferase (EC 2), hydrolase (EC 3), lyase (EC 4), isomerase (EC 5), or ligase (EC 6). The EC numbers are based on the enzyme nomenclature recommendations of the Nomenclature Committee of the International Union of Biochemistry and Molecular Biology (1992), including its supplements published between 1993 and 1999. Preferably, the enzyme is a hydrolase (EC 3).

[0241] In a preferred embodiment, the enzyme is selected from the group consisting of:

[0242] Protease, amylase, lipase, cellulase, mannanase, hemicellulase, phospholipase, esterase, pectinase, lactase, peroxidase, xylanase, keratinase, pectic acid lyase, keratinase, reductase, oxidase, phenol oxidase, lipoxygenase, ligninase, amylopectinase, tanninase, pentosanase, malicase, β-glucanase, arabinosidase, hyaluronidase, chondroitinase, laccase, nuclease, deoxyribonuclease, phosphate diphosphate The enzyme comprises esterases, phytases, carbohydrate enzymes, galactanases, xanthan gumases, xyloglucanases, oxidoreductases, hydrolases, aminopeptidases, asparaginases, carbohydrate enzymes, carboxypeptidases, catalases, chitinases, cyclodextrin glycosyltransferases, α-galactosidases, β-galactosidases, glucosylamylases, α-glucosidases, β-glucosidases, invertases, ribonucleases, transglutaminases, and dispersins, as well as combinations of at least two of the aforementioned types. More preferably, the enzyme is selected from the group consisting of proteases, amylases, lipases, cellulases, mannanases, xylanases, deoxyribonucleases, dispersins, pectinases, oxidoreductases, and keratins, as well as combinations of at least two of the aforementioned types. Most preferably, the enzyme is a protease, preferably a serine protease, and more preferably a subtilisin.

[0243] Preferably, the protease is a protease having at least 90% sequence identity with SEQ ID NO: 22 of EP 1921147 B1 and having an amino acid substitution R101E (according to the BPN number). Preferably, the amylase is an amylase having at least 90% sequence identity with SEQ ID NO: 54 of WO 2021032881A1.

[0244] The compositions of the present invention may contain one type of enzyme or more than one different type of enzyme, such as amylase and protease, or more than one enzyme of the same type, such as two or more different proteases, or a mixture thereof, such as amylase and two different proteases.

[0245] The enzyme may be incorporated into the composition in an effective amount sufficient to provide for achieving beneficial effects, preferably for primary and / or secondary washing effects, such as anti-ashing or anti-pilling effects (e.g., in the case of cellulase). Preferably, the enzyme is present in the composition at a level of about 0.00001% to about 5% by weight of the composition, preferably about 0.00001% to about 2%, more preferably about 0.0001% to about 1%, or even more preferably about 0.001% to about 0.5% of enzyme protein.

[0246] Technicians will understand that the enzymes mentioned above can also be part of microorganisms, probiotics, and / or prebiotics.

[0247] Preferably, the enzyme-containing composition further comprises an enzyme stabilizing system.

[0248] Preferably, the enzyme-containing composition described herein comprises about 0.001% to about 10%, about 0.005% to about 8%, or about 0.01% to about 6% by weight of the composition of an enzyme stabilizing system. The enzyme stabilizing system can be any stabilizing system compatible with the enzyme.

[0249] Preferably, the enzyme stabilizing system comprises at least one compound selected from the group consisting of: polyols (preferably 1,3-propanediol, ethylene glycol, glycerol, 1,2-propanediol, or sorbitol), inorganic salts (preferably CaCl2, MgCl2, or NaCl), short-chain (preferably C1-C3) carboxylic acids or their salts (preferably formic acid, formate (preferably sodium formate), acetic acid, acetate, or lactate), borates, boric acid, boronic acid (preferably 4-formylphenylboronic acid (4-FPBA)), peptide aldehydes (preferably Z-VAL-H or Z-GAY-H), peptide acetals, and peptide aldehyde bisulfite adducts. Preferably, the enzyme stabilizing system comprises a combination of at least two compounds selected from the group consisting of salts, polyols, and short-chain carboxylic acids, and preferably one or more compounds selected from the group consisting of borates, boric acid, boronic acid (preferably 4-formylphenylboronic acid (4-FPBA)), peptide aldehydes, peptide acetals, and peptide aldehyde bisulfite adducts. In particular, if a protease is present in the composition, a protease inhibitor may be added, preferably selected from borates, boric acid, boronic acid (preferably 4-FPBA), peptide aldehydes (preferably peptide aldehydes such as Z-VAL-H or Z-GAY-H), peptide acetals, and peptide aldehyde bisulfite adducts.

[0250] The compositions according to the invention may contain one or more bleaching agents. Preferred bleaching agents are selected from sodium perborate, anhydrous or, for example, as a monohydrate or as a tetrahydrate or so-called dihydrate, sodium percarbonate, anhydrous or, for example, as a monohydrate, and sodium persulfate, wherein the term "persulfate" in each case includes salts of persulfate H2SO5 as well as perdisulfate.

[0251] In view of this, the alkali metal salt can also be an alkali metal bicarbonate, an alkali metal perborate, or an alkali metal persulfate in each case. However, in each case, a dialkali metal salt is preferred.

[0252] The formulations according to the invention may contain one or more bleaching catalysts. The bleaching catalyst may be selected from oxaziridinium-based bleaching catalysts, bleaching-promoting transition metal salts or transition metal complexes, such as manganese-, iron-, cobalt-, ruthenium-, or molybdenum-salen complexes or carbonyl complexes. Manganese, iron, cobalt, ruthenium, molybdenum, titanium, vanadium, and copper complexes having nitrogen-containing tripod ligands, as well as cobalt-, iron-, copper-, and ruthenium-amine complexes, may also be used as bleaching catalysts.

[0253] The formulations according to the invention may contain one or more bleaching activators, such as tetraacetylethylenediamine, tetraacetylmethylenediamine, tetraacetylglycolurea, tetraacetylhexanediamine, acylated phenol sulfonates such as n-nonanoyloxybenzenesulfonate or isonanoyloxybenzenesulfonate, (S)NOBS, LOBS, DOBA, PAP, N-methylmorpholinium acetonitrile (“MMA salt”), trimethylammonium acetonitrile, N-imides such as N-nonanoylsuccinimide, 1,5-diacetyl-2,2-dioxohexahydro-1,3,5-triazine (“DADHT”), or nitrile quaternary ammonium (trimethylammonium acetonitrile).

[0254] As a precursor to H2O2, consider peroxides, which are every compound capable of producing hydrogen peroxide in aqueous solution, such as the organic and inorganic peroxides known in the literature and commercially available, which bleach textiles at conventional washing temperatures, such as 10°C to 95°C.

[0255] However, inorganic peroxides, such as persulfates, perborates, percarbonates, and / or persilicates, are preferably used. These peroxides are typically used in amounts of 2-80 wt%, preferably 4-30 wt%, based on the weight of the composition.

[0256] Typically, the following describes it in more detail as having equation (1) The compound is present in the composition in an amount of 0.05-15 wt% based on the total weight of the composition, preferably 0.1 to 10 wt%.

[0257] Examples of suitable inorganic peroxides are sodium perborate tetrahydrate or sodium perborate monohydrate, sodium percarbonate, and inorganic peroxyacid compounds, such as potassium persulfate (MPS). If an organic or inorganic peroxyacid is used as the peroxide compound, its amount is typically in the range of about 2-80 wt%, preferably 4-30 wt%, based on the weight of the composition.

[0258] Organic peroxides are, for example, single or multiple peroxides, urea peroxides, combinations of C1-C4 alkanol oxidases and C1-C4 alkanols (such as methanol oxidase and ethanol as described in WO 95 / 07972), and alkyl hydroxy peroxides, such as cumene hydroperoxide and tert-butyl hydroperoxide.

[0259] These peroxides can exist in various crystalline forms and have different water contents, and they can also be used with other inorganic or organic compounds to improve their storage stability.

[0260] Peroxy acids can also be used as oxidizing agents. One example is an organic monoperacid having formula (1). ,

[0261] in

[0262] M represents hydrogen or a cation.

[0263] R 19 Indicates unsubstituted C1-C 18 Alkyl; Substituted C1-C 18 Alkyl; unsubstituted aryl; substituted aryl; -(C1-C6 alkylene)-aryl, wherein the alkylene and / or the alkyl group may be substituted; and phthalimide C1-C8 alkylene, wherein the phthalimide and / or the alkylene group may be substituted.

[0264] Preferred single organic peroxy acids and their salts are those having the following formula: ,

[0265] in

[0266] M represents hydrogen or an alkali metal, and

[0267] R' 19 This indicates unsubstituted C1-C4 alkyl; phenyl; -C1-C2 alkylene-phenyl or

[0268] Phthalimide C1-C8 alkylene group.

[0269] CH3COOOH and its alkali metal salts are particularly preferred.

[0270] e-phthalimide peroxyhexanoic acid and its alkali metal salt (PAP) are particularly preferred.

[0271] Also suitable are diperoxic acids, such as 1,12-disperoxydodecanoic acid (DPDA), 1,9-disperoxyazeloic acid, diperoxadecanoic acid, diperoxadecanoic acid, diperoxisophthalic acid, 2-decyldisperoxybutane-1,4-diacid and 4,4'-sulfonylbisperoxybenzoic acid.

[0272] In some cases, the use of additional bleach activators can be advantageous.

[0273] The term bleaching activator is often used synonymously with peroxy acid bleaching precursor. All of the above-mentioned peroxy compounds can be used alone or in combination with peroxy acid bleaching precursors.

[0274] These precursors are the corresponding carboxylic acids, carboxylic anhydrides, carbonyl chlorides, amides, or esters, which can form peroxyacids upon hydrolysis. Such reactions are generally known.

[0275] Peroxyacid bleaching precursors are known and described in detail in the literature, such as in British Patents 836988; 864,798; 907,356; 1,003,310 and 1,519,351; German Patents 3,337,921; EP-A-0185522; EP-A-0174132; EP-A-0120591; and US Patents 1,246,339; 3,332,882; 4,128,494; 4,412,934 and 4,675,393.

[0276] Suitable bleaching activators include those with O- and / or N-acyl groups and / or unsubstituted or substituted benzoyl groups. Preferred are polyacylated alkylene diamines, especially tetraacetylethylenediamine (TAED); acylated glycoureas, especially tetraacetyldiol urea (TAGU), N,N-diacetyl-N,N-dimethylurea (DDU); sodium 4-benzoyloxybenzenesulfonate (SBOBS); sodium 1-methyl-2-benzoyloxybenzene-4-sulfonate; sodium 4-methyl-3-benzoyloxybenzoate; trimethylammonium tolueneoxybenzenesulfonate; acylated triazine derivatives, especially 1,5-diacetyl-2,4-dioxohexahydro-1,3,5-triazine (DADHT); compounds having formula (10):

[0277]

[0278] Where R 22It is a sulfonate group, a carboxylic acid group, or a carboxylic ester group, and wherein R 21 Is it a straight chain or a branched chain (C7-C)? 15 Alkyl groups, especially activators known by the names SNOBS, SLOBS, and DOBA; acylated polyols, especially triacetin, ethylene glycol diacetate, and 2,5-diacetoxy-2,5-dihydrofuran; and also acetylated sorbitol and mannitol and acylated sugar derivatives, especially pentaacetyl glucose (PAG), sucrose polyacetate (SUPA), pentaacetylfructose, tetraacetylxylose, and octaacetyllactose, as well as acetylated, optionally N-alkylated glucosamine and gluconolactone. Combinations of conventional bleaching activators known from German patent application DE-A-44 43 177 may also be used. Nitrile compounds that form perimino acids with peroxides are also considered as bleaching activators.

[0279] Another class of useful peroxyacid bleaching precursors are cationic ones, namely quaternary ammonium-substituted peroxyacid precursors, such as those disclosed in U.S. Patent Nos. 4,751,015 and 4,397,757, EP-A 0 284292, and EP-A-331,229. Examples of such peroxyacid bleaching precursors are: 2-(N,N,N-trimethylammonium)ethyl-4-sulfophenyl carbonate sodium chloride- (SPCC), N-octyl,N,N-dimethyl-N10-carboxyphenoxydecyl ammonium chloride- (ODC), 3-(N,N,N-trimethylammonium)propyl-4-sulfophenylcarboxylate sodium salt, and N,N,N-trimethylammonium tolueneoxybenzenesulfonate.

[0280] Additional bleaching catalysts may also be used, such as transition metal complexes disclosed in EP1194514, EP 1383857 or WO 04 / 007657.

[0281] Formulations according to the invention may contain one or more corrosion inhibitors. In this case, this should be understood to include those compounds that inhibit the corrosion of metals. Examples of suitable corrosion inhibitors are triazoles, particularly benzotriazole, bisbenzotriazole, aminotriazole, alkylaminotriazole, and phenol derivatives, such as hydroquinone, pyrocatechol, hydroxyhydroquinone, gallic acid, phloroglucinol, or pyroglucinol.

[0282] In one embodiment of the invention, the formulation according to the invention comprises a total of 0.1% to 1.5% corrosion inhibitor by weight.

[0283] The formulations according to the invention may further comprise cleaning polymers and / or stain-removing polymers.

[0284] Additional cleaning polymers may include, but are not limited to: "polyfunctional alkoxylated polyethyleneimine" (e.g., BASF's Sokalan® HP20), "polyfunctional alkoxylated diamine" (e.g., BASF's Sokalan® HP96), BASF's Sokalan® SR400 A, and terephthalic acid-based polyesters, such as Clariant's TexCare®, including TexCare® SRN 170, TexCare® SRN 172, TexCare® SRN 260, TexCare® SRN260 SG Terra, and TexCare® SRA 300, as well as different combinations of all the aforementioned polymers.

[0285] Suitable polyfunctional alkoxylated polyethyleneimines are typically ethoxylated polyethyleneimines having a weight-average molecular weight (Mw) in the range of 3,000 to 250,000, preferably 5,000 to 200,000, more preferably 8,000 to 100,000, even more preferably 8,000 to 50,000, even more preferably 10,000 to 30,000, and most preferably 10,000 to 20,000 g / mol. Suitable polyfunctional alkoxylated polyethyleneimines have ethylene oxide side chains comprising 80 wt.% to 99 wt.%, preferably 85 wt.% to 99 wt.%, more preferably 90 wt.% to 98 wt.%, and most preferably 93 wt.% to 97 wt.% or 94 wt.% to 96 wt.% based on the total weight of the material. Ethoxylated polyethyleneimines are typically based on a polyethyleneimine core and a polyethylene oxide shell. A suitable polyethyleneimine core molecule is a polyethyleneimine having a weight-average molecular weight Mw in the range of 500 to 5000 g / mol. Preferably, a molecular weight of 500 to 1000 g / mol is used, and even more preferably, a Mw of 600 to 800 g / mol is used. Then, the ethoxylated polymer has an average of 5 to 50, preferably 10 to 35, and even more preferably 20 to 35 ethylene oxide (EO) units / NH-functional groups.

[0286] Suitable polyfunctional alkoxylated diamines are typically ethoxylated C2 to C3. 12The alkylene diamine, preferably hexamethylene diamine, is further quaternized and optionally sulfated (wherein the diamine is not ethylenediamine). Typical polyfunctional alkoxylated diamines have a weight-average molecular weight (Mw) in the range of 2000 to 10000, more preferably 3000 to 8000, and most preferably 4000 to 6000 g / mol. In a preferred embodiment of the invention, ethoxylated hexamethylene diamine, which is further quaternized and sulfated, may be used, containing an average of 10 to 50, preferably 15 to 40, and even more preferably 20 to 30 ethylene oxide (EO) groups / NH-functional groups, and preferably has two cationic ammonium groups and two anionic sulfate groups.

[0287] Suitable polymers also include graft polymers, which contain

[0288] (A) A polyepoxide backbone (A) comprising at least one structural unit derived from a monomer group consisting of ethylene oxide, 1,2-epoxypropane, 1,2-epoxybutane, 2,3-epoxybutane, 1,2-epoxypentane, and 2,3-epoxypentane, and

[0289] (B) A polymer side chain (B) grafted onto the polyepoxide backbone (A), wherein the polymer side chain (B) comprises at least one vinyl ester monomer (B1) and optionally N-vinylpyrrolidone as an additional monomer (B2).

[0290] It should be noted that the cleaning composition of the present invention may also contain at least one propoxylated ethylenediamine of the present invention and at least one other propoxylated diamine that does not form part of the claims, such as propoxylated ethylenediamine having an average of less than 28 PO units / mol EDA or an average of more than 52 PO units / mol EDA.

[0291] In a preferred embodiment of the invention, the cleaning composition may contain at least one polyfunctional alkoxylated polyethyleneimine and / or at least one polyfunctional alkoxylated diamine to improve cleaning performance, such as preferably improving stain removal ability, especially the primary detergency of laundry detergents on particulate stains on polyester fabrics. The polyfunctional polyethyleneimine or polyfunctional diamine or mixture thereof described above may be added to the laundry detergent and cleaning composition in an amount typically 0.05 to 15 wt.%, preferably 0.1 to 10 wt.%, and more preferably 0.25 to 5 wt.%, and even as low as up to 2 wt.%, based on the specific overall composition (containing other components and water and / or solvents).

[0292] In another preferred embodiment of the invention, the cleaning composition may contain at least one terephthalic acid-based polyester as a stain-removing polymer to improve the whiteness of the fabric after washing, especially the whiteness of polyester fabrics.

[0293] Therefore, one aspect of the present invention is a laundry detergent composition, particularly a liquid laundry detergent, comprising (i) at least one compound of the present invention and (ii) at least one compound selected from polyfunctional alkoxylated polyethyleneimine, polyfunctional alkoxylated diamine and terephthalic acid-based polyesters, and mixtures thereof.

[0294] In one embodiment of the invention, the ratio of the at least one compound of the invention to (ii) the at least one compound selected from polyfunctional polyethyleneimine and polyfunctional diamine and mixtures thereof is 10:1 to 1:10, preferably 5:1 to 1:5 and more preferably 3:1 to 1:3.

[0295] Laundry products containing the compounds of the present invention may also contain at least one antimicrobial agent (also commonly referred to as a preservative).

[0296] The composition may contain one or more antimicrobial agents and / or preservatives as listed on pages 35 to 39 of patent WO 2021 / 115912 A1.

[0297] Of particular interest are the following antimicrobial agents and / or preservatives:

[0298] 4,4'-Dichloro-2-hydroxydiphenyl ether (CAS No. 3380-30-1), also known as 5-chloro-2-(4-chlorophenoxy)phenol, diclosan, DCPP, is commercially available as a 30 wt% solution of 4,4'-dichloro-2-hydroxydiphenyl ether in 1,2-propanediol under the trade name Tinosan® HP 100 (BASF); 2-phenoxyethanol (CAS No. 122-99-6, also known as phenoxyethanol, methylphenyl glycol, phenoxyethanol, ethylene glycol phenyl ether, ethylene glycol monophenyl ether, Protectol® PE); 2-bromo-2-nitropropane-1,3-diol (CAS No. 52-51-7, also known as 2-bromo-2-nitro-1,3-propanediol, Bronopol®, Protectol® BN, Myacide). AS); Glutaraldehyde (CAS No. 111-30-8, other names: 1-5-glutaraldehyde, pentyl-1,5-dialdehyde, glutaral, glutardialdehyde, Protectol® GA, Protectol® GA 50, Myacide® GA); Glyoxal (CAS No. 107-22-2; other names: ethandial, oxylaldehyde, 1,2-glyoxal, Protectol® GL); 2-Butyl-benzo[d]isothiazol-3-one (BBIT, CAS No. 4299-07-4); 2-Methyl-2H-isothiazol-3-one (MIT, CAS No. 2682-20-4); 2-Octyl-2H-isothiazol-3-one (OIT, CAS No. 26530-20-1); 5-Chloro-2-methyl-2H-isothiazol-3-one (CIT, CMIT, CAS No. 26172-55-4); 5-Chloro-2-methyl-2H-isothiazol-3-one (CMIT, EINECS 247-500-7) and 2-Methyl-2H-isothiazol-3-one (MIT, EINECS Mixtures of 220-239-6 (a mixture of CMIT / MIT, CAS No. 55965-84-9); 1,2-benzisothiazol-3(2H)-one (BIT, CAS No. 2634-33-5); hexano-2,4-dienoic acid (sorbic acid, CAS No. 110-44-1) and its salts, such as calcium sorbate, sodium sorbate, potassium (E,E)-hexano-2,4-dienoic acid (potassium sorbate, CAS No. 24634-61-5); lactic acid and its salts; L-(+)-lactic acid (CAS No. 79-33-4).Benzoic acid and its sodium salts (CAS No. 65-85-0, CAS No. 532-32-1) and benzoates, such as ammonium benzoate, calcium benzoate, magnesium benzoate, MEA-benzoate, potassium benzoate; salicylic acid and its salts, such as calcium salicylate, magnesium salicylate, MEA salicylate, sodium salicylate, potassium salicylate, TEA salicylate; benzalkonium chloride, benzalkonium bromide and benzalkonium saccharin, such as benzalkonium chloride, benzalkonium bromide, benzalkonium saccharin (CAS Nos. 8001-54-5, 63449-41-2, 91080-29-4). 68989-01-5, 68424-85-1, 68391-01-5, 61789-y71-7, 85409-22-9; Didecyl dimethyl ammonium chloride (DDAC, CAS No. 68424-95-3 and CAS No. 7173-51-5); N-(3-aminopropyl)-N-dodecylpropane-1,3-diamine (diamine, CAS No. 2372-82-9); Peracetic acid (CAS No. 79-21-0); Hydrogen peroxide (CAS No. 7722-84-1).

[0299] The antimicrobial agent is added to the composition at a concentration of 0.001% to 10% relative to the total weight of the composition.

[0300] Preferably, the composition contains 0.1% to 2% of 2-phenoxyethanol or 0.005% to 0.6% of 4,4'-dichloro-2-hydroxydiphenyl ether (DCPP).

[0301] Therefore, the present invention further covers a method for preserving the aqueous composition according to the invention against microbial contamination or growth, the method comprising adding 2-phenoxyethanol. The present invention further covers a method for providing antimicrobial action to textiles after treatment with a solid laundry detergent (e.g., powder, granules, capsules, tablets, sticks, etc.), liquid laundry detergent, softener, or post-rinse agent containing 4,4'-dichloro-2-hydroxydiphenyl ether (DCPP).

[0302] In another embodiment, the present invention also covers a composition comprising the compounds of the present invention as described above, further comprising an antimicrobial agent disclosed below (preferably selected from the group consisting of 2-phenoxyethanol), more preferably comprising the antimicrobial agent in an amount ranging from 2 ppm to 5% by weight of the composition; and even more preferably comprising 0.1% to 2% phenoxyethanol.

[0303] In another embodiment, the present invention also covers a method for preserving an aqueous composition against microbial contamination or growth, the composition comprising the compounds of the present invention as described above, preferably a detergent composition, the method comprising adding at least one antimicrobial agent selected from the antimicrobial agents disclosed below, preferably 2-phenoxyethanol.

[0304] In other embodiments, the present invention also covers a composition, preferably a cleaning composition, more preferably a liquid laundry detergent composition or a liquid hand dish composition, even more preferably a liquid laundry detergent composition or a liquid fabric softener composition for use in laundry, such composition comprising the compounds of the present invention as described above, and such composition further comprising 4,4'-dichloro-2-hydroxydiphenyl ether at a concentration of 0.001% to 3%, preferably 0.002% to 1%, more preferably 0.01% to 0.6% by weight of the composition.

[0305] In another embodiment, the present invention also covers a method for washing fabrics or cleaning hard surfaces, the method comprising treating the fabrics or hard surfaces with a cleaning composition, more preferably a liquid laundry detergent composition or a liquid hand tableware composition, even more preferably a liquid laundry detergent composition or a liquid fabric softener composition for use in laundry, such composition comprising the compounds of the present invention as described above, such composition further comprising 4,4'-dichloro-2-hydroxydiphenyl ether.

[0306] As used herein, the term "dye fixative" refers to compounds that reduce or even stop dye penetration into colored fabrics during the washing process. Dye fixatives include, but are not limited to, cationic dye fixatives, crosslinking fixatives, and formaldehyde-based fixatives. These compounds are well-known to those skilled in the art and are commercially available from BASF SE, Huntsman, Archroma, Fineotex, Biotex Malaysia, or Dystar. Exemplary but not limiting dye fixatives include Basilen fixative F-RP, Albafix ECO, Finofix NF, poly DADMAC, and polyamines (DCDA-DETA, epichlorohydrin-DMA, epichlorohydrin-DETA, etc.).

[0307] The formulations according to the invention may also contain water and / or additional organic solvents, such as ethanol or propylene glycol.

[0308] Other optional ingredients may include, but are not limited to, viscosity modifiers, cationic surfactants, foam promoters or defoamers, fragrances, dyes, optical brighteners, and dye transfer inhibitors.

[0309] (b) General cleaning compositions and formulations

[0310] In addition to all other ingredients mentioned, the liquid formulations disclosed in this section may also contain 0 to 2%, preferably about 1%, of 2-phenoxyethanol.

[0311] In addition to all other ingredients mentioned, the liquid formulations disclosed above and below may also contain 0-0.2%, preferably about 0.15%, of 4,4'-dichloro-2-hydroxydiphenyl ether. In addition to all other ingredients mentioned, the bleach-free solid laundry compositions may also contain 0-0.2%, preferably about 0.15%, of 4,4'-dichloro-2-hydroxydiphenyl ether.

[0312] The formulations disclosed in this section may, in addition to all other ingredients mentioned, contain one or more enzymes selected from those disclosed above, more preferably proteases and / or amylases, wherein even more preferably the proteases are proteases having at least 90% sequence identity with SEQ ID NO: 22 of EP 1921147 B1 and having amino acid substitution R101E (according to the BPN number), and wherein the amylases are amylases having at least 90% sequence identity with SEQ ID NO: 54 of WO 2021032881 A1, wherein the one or more enzymes are preferably present in the formulation at a level of about 0.00001% to about 5% by weight of the composition, preferably about 0.00001% to about 2%, more preferably about 0.0001% to about 1%, or even more preferably about 0.001% to about 0.5% of the enzyme protein.

[0313] The following compositions (including those in the table) disclose certain types of general-purpose cleaning compositions corresponding to typical compositions associated with typical washing conditions typically employed in regions and countries around the world. At least one of the inventive compounds may be added to one or more formulations in suitable amounts as outlined herein.

[0314] When the illustrated composition does not contain any of the compounds of the present invention, it is a comparative composition. When it contains any of the compounds of the present invention, particularly in amounts described herein as preferred, more preferred, etc., such compositions are considered to fall within the scope of the present invention.

[0315] In a preferred embodiment, the at least one substituted 1,3-dioxolane sulfate (as defined in the examples herein, particularly any one of Examples 1 to 11; also referred to herein as the "compound of the invention") is used in a laundry detergent.

[0316] The liquid laundry detergent according to the present invention comprises the following:

[0317]

[0318] The preferred liquid laundry detergent according to the present invention comprises the following:

[0319]

[0320] The solid laundry detergent (such as, for example, powder, granules, or tablets) according to the present invention comprises the following:

[0321]

[0322] The total of the components is 100%.

[0323] The preferred solid laundry detergent according to the present invention comprises the following:

[0324]

[0325] In a preferred embodiment, the polymer according to the invention is used in a detergent for manual dishwashing.

[0326] The liquid manual dishwashing detergent according to the present invention comprises the following:

[0327]

[0328] The preferred liquid manual dishwashing detergent according to the present invention comprises the following:

[0329]

[0330] Because the surfactants of the present invention can be biodegradable, and especially because cleaning formulations typically have a pH of about 7 or higher, and additionally often contain enzymes—which are included in such cleaning formulations to degrade biodegradable substances such as greases, proteins, polysaccharides, etc., present in stains and dust that should be removed by the cleaning composition—several factors need to be considered when formulating those potentially biodegradable surfactants of the present invention. Suitable formulations of this kind are known in principle and include formulations in solid form—where enzymes and surfactants can be separated by coating or added to mixed individual particles—as well as formulations in liquid and semi-liquid form, where surfactants and enzymes can be separated by formulation in different compartments (such as different compartments of multi-compartment pouches or bottles with different chambers), where liquid is poured out from the compartments simultaneously in predetermined amounts to ensure that each component in each compartment is applied in an appropriate amount at each individual point of use. Such multi-compartment pouches and bottles are also known to those skilled in the art.

[0331] The following illustrates certain types of general-purpose cleaning compositions, corresponding to typical compositions associated with typical washing conditions typically employed in regions and countries around the world. At least one compound of the invention may be added to one or more formulations in suitable amounts as outlined herein.

[0332] Table 1: General formulations of laundry detergent compositions according to the present invention:

[0333]

[0334] Table 2: Liquid washing frame preparation according to the present invention:

[0335]

[0336] Formulations that do not contain the compounds of this invention are comparative examples.

[0337] Table 2 - Continued: Liquid washing frame preparations according to the present invention:

[0338]

[0339] Formulations that do not contain the compounds of this invention are comparative examples.

[0340] Table 3: Laundry powder frame formulation according to the present invention:

[0341]

[0342] Table 3-continued: Laundry powder frame formulation according to the present invention:

[0343]

[0344] Table 4: Liquid manual dishwashing frame preparation according to the present invention:

[0345]

[0346] The following examples are intended to further illustrate the invention but do not limit its scope.

[0347] This invention encompasses the specific embodiments described throughout this disclosure as part of the invention; various additional options are disclosed in the specification as “optional,” “preferred,” “more preferred,” “even more preferred,” or “most preferred” (or “preferred,” etc.), and options of specific embodiments may be selected individually and independently (unless such independent selection is impossible due to the nature of the feature or if such independent selection is explicitly excluded) and then combined with any other embodiment (where other such options and preferences may also be selected individually and independently, unless such independent selection is impossible due to the nature of the feature or if such independent selection is explicitly excluded), wherein each and any and all such possible combinations are included as separate embodiments as part of the invention. Example

[0348] I) Synthesis:

[0349] General

[0350] A long-chain aliphatic aldehyde is reacted with a triol containing at least four carbon atoms and hydroxyl groups at positions 1 and 2 in the presence of an acidic catalyst. The resulting acetal is sulfated with sulfur trioxide and neutralized with an alkali (e.g., aqueous sodium hydroxide solution) in a falling film reactor, or sulfated with chlorosulfonic acid (optionally in the presence of a solvent) and neutralized with an alkali (e.g., aqueous sodium hydroxide solution), or reacted with aminosulfonic acid (in the presence of urea and optionally in the presence of a solvent). Optionally, a buffer solution is added to maintain a pH above 7. The degree of sulfation is > 90%.

[0351] Examples of the present invention

[0352] a) 2-Undecyl-4-hydroxyethyl-1,3-dioxolane

[0353] Example 1 of the present invention (IE1)

[0354] Dodecaldehyde was freshly distilled. Dodecaldehyde (46.2 g, 0.245 mol, 1.0 equivalent), 1,2,4-butanetriol (27.8 g, 0.262 mol, 1.07 equivalent), and alkylbenzene sulfonic acid (C10C13-Ph-SO3H, 0.34 g, 0.001 mol, 0.004 equivalent) were mixed in a 250 ml glass container and stirred at 50°C under a nitrogen atmosphere for 2 hours. To quench the reaction, 150 ml of a 5 wt% NaHCO3 solution in water was added. The organic phase was separated. The aqueous phase was extracted with ethyl acetate (3 x 150 ml). All organic phases were combined, dried over sodium sulfate, and the solvent was removed at 60°C and 10 mbar. According to proton NMR, dodecaldehyde was completely converted to the desired acetal.

[0355] b) 2-Undecyl-4-ethylsulfate-1,3-dioxolane sodium salt

[0356] Example 2 of the present invention (IE2)

[0357] In a 500 ml container, 2-undecyl-4-hydroxyethyl-1,3-dioxolane (20 g, 0.073 mol, 1.0 equivalent) was dissolved in dichloromethane (140 ml) and cooled to 5°C. Nitrogen gas was bubbled through the mixture. To reduce the concentration of the sulfating agent and avoid undesirable side reactions due to prolonged stirring, 1,4-dioxane (12.9 g, 0.146 mol, 2.0 equivalent) was added. Then, chlorosulfonic acid (8.5 g, 0.073 mol, 1.0 equivalent) was added dropwise over 20 minutes at 5°C–10°C. The reaction mixture was heated to 10°C and stirred for 30 minutes. The solution was added to a 2-liter container containing 600 ml of 10°C cold water containing NaOH (3.96 g, 0.099 mol, 1.36 equivalent). Adjust the pH to 10.3 and add buffer (NaHCO3 / Na2CO3). Remove the solvent at 60°C and 140 mbar. The degree of sulfation is 90% according to proton NMR. Optionally, dissolve the crude product in water to obtain a solution of 20 wt% surfactant in water.

[0358] For routes without 1,4-dioxane, SO3-NEt3 can be used as the sulfation reagent because it is milder than chlorosulfonic acid. In a falling film reactor, sulfation with sulfur trioxide can be regulated to reduce side reactions (by adjusting temperature and reaction time).

[0359] Comparison Examples

[0360] The following structures are disclosed in US 20230174895 and were synthesized for comparison with the compounds of this invention.

[0361] a) 2-Undecyl-4-hydroxymethyl-1,3-dioxolane (CE1) : 2-Undecyl-5-hydroxy-1,3-dioxane (CE2) = 67 : 33 or 43 : 57

[0362] Compare with Example 1 (CE1)

[0363] Comparative Example 2 (CE2)

[0364] The acetalization of dodecanal with glycerol in the presence of alkylbenzenesulfonic acid (C10-C13-Ph-SO3H) was carried out in a manner similar to the synthesis in Example 1 of the present invention. If the reaction mixture was stirred for only 1 hour, a 67:33 mixture of CE1:CE2 was obtained. If the reaction mixture was stirred for 5 hours, a 43:57 mixture of CE1:CE2 was obtained.

[0365] b) Sodium 2-undecyl-4-methylsulfate-1,3-dioxolane (CE3): Sodium 2-undecyl-5-sulfate-1,3-dioxane (CE4) = 67:33 or 43:57

[0366] Comparative Example 3 (CE3)

[0367] Compare Example 4 (CE4)

[0368] The mixture of CE1 and CE2 was sulfated in a manner similar to that described previously for Example 2 of the present invention. The degree of sulfation was approximately 90%.

[0369] II) Functional Testing:

[0370] As shown in Table 1, compound IE1 (of the present invention) is a liquid at 20°C, while the mixture of CE1 and CE2 is a solid at 20°C (comparative example). In the case of compound IE1, sulfation with sulfur trioxide on a falling film reactor is feasible at low temperatures such as 20°C, which can reduce energy costs and decrease the formation of byproducts.

[0371] Table 1: Appearance of acetal at 20°C

[0372]

[0373] As shown in Table 2, in tests concerning foaming properties (EN 12728, DIN 53902), using 2 g of material per liter in hard water (10°dH) at 40°C, Example 2 of the present invention demonstrated significantly stronger foaming properties (i.e., 640 ml) compared to a mixture of CE3 and CE4 (i.e., 160 ml or 470 ml). Strong foaming properties are of interest, for example, for manual dishwashing. Particularly in hard water (such as water containing a high concentration of calcium ions).

[0374] Table 2: Foaming capacity of 2 g surfactant per liter of hard water (10°dH) at 40°C using the foaming method

[0375]

[0376] Table 3 discloses that IE2 (of the present invention) exhibits a much lower dynamic surface tension (i.e., 45.1 mN / m) compared to a mixture of CE3 and CE4 (i.e., 66.6 mN / m or 63.4 mN / m, respectively). This lower dynamic surface tension indicates that the surfactant is more readily available at the interface (e.g., at the oil-water interface) and can begin removing, for example, oil earlier, which is relevant to I&I processes, laundry, and dishwashing.

[0377] Table 3: Dynamic surface tension of 1 g surfactant per liter of hard water (10°dH) after 0.1 s at room temperature

[0378]

[0379] Table 4 discloses that IE2 (of the present invention) exhibits significantly lower interfacial tensions (i.e., 0.8 and 1.5 mN / m) against olive oil or n-hexadecane compared to mixtures of compounds CE3 and CE4 (i.e., 2.3 and 7.7 mN / m or 2.6 and 5.5 mN / m). This lower interfacial tension indicates that the surfactant is able to remove oil in a better manner. Olive oil is a triglyceride and thus a model oil for dirt in laundry or dishwashing; n-hexadecane is a model oil, for example, an aliphatic oil from the lubricant industry.

[0380] Table 4: Interfacial tension of 1 g surfactant per liter of hard water (10°dH) after 3 min at room temperature

[0381]

[0382] Application tests conducted using the Launder-O-meter for color fastness to washing.

[0383] The washing performance of the compounds of the present invention was determined as follows.

[0384] Before washing, the L value of a single stain on a multi-stain tester was measured using a MACH 5 from CFT / Colour Consult. a b The fabric was then washed at 30°C with cotton ballast fabric and 20 steel balls in water with a defined hardness. After washing, the fabric was rinsed, tumble-dried, and air-dried.

[0385] After drying, L was measured using a MACH 5 from CFT / Color Consulting. a b The dE value determines the washing performance for a single stain. The dE value is calculated from the individual values ​​before and after washing. The two stains from the test sample are summed. A higher value indicates better performance.

[0386] Washing conditions:

[0387]

[0388] Manufacturers: wfk-Testgewebe, 10 Christenfeld, 41379 Brüggen; Swissastest Testmaterialien AG, 12 Mövenstraße, CH-9015 St. Gallen

[0389] Table 5 shows the results of the primary detergency at 30°C in the wash fastness tester. Compared with the control without surfactant, EI2 removed sebum-rich stains more effectively.

[0390] Table 5: Primary detergency of two types of sebum-rich stained fabrics after 60 minutes in hard water at 30°C using a wash fastness tester, with and without surfactants.

[0391] .

Claims

1. A compound having a structure according to formula (I) Equation (I) in R1 is a C8 to C27 alkyl or C8 to C27 alkenyl. R4 is hydrogen, a C2 to C18 alkyl group, or a C2 to C18 alkenyl group. R2 is (i) (ii) 、or (iii) , M is selected from the following groups: hydrogen, Na, K, ammonia, protonated amines, and protonated amino alcohols; m is an integer with values ​​from 1 to 4; The dashed lines indicate the bonds bonded to the oxygen atom in formula (I), and n is an integer with values ​​from 1 to 9.

2. The compound according to claim 1, wherein, R1 is a C10 to C17 alkyl or C10 to C17 alkenyl, preferably a C10 to C17 alkyl.

3. The compound according to claim 1 or 2, wherein, R2 is Furthermore, the dashed line and M are as defined above, and preferably M is Na.

4. The compound according to any one of claims 1 to 3, wherein, i)n is an integer with values ​​from 1 to 3; and ii) R4 is hydrogen.

5. The compound according to any one of claims 1 to 4, wherein, M is selected from the following groups: hydrogen, Na, K, and ammonia.

6. A method for preparing the compound according to any one of claims 1 to 5, the method comprising: i) Make the aldehyde or ketone according to formula (II) Equation (II), Wherein R3 is a C8 to C27 alkyl or C8 to C27 alkenyl, and R4 is hydrogen, a C2 to C18 alkyl group, or a C2 to C18 alkenyl group. It reacts with straight-chain triols containing 4 to 12 carbon atoms, wherein the hydroxyl groups are at the 1-, 2-, and ω-positions, in the presence of an acidic catalyst. To obtain the compound according to claims 1 to 5, wherein R2 is And the dashed line is as defined in claim 1, and optionally... ii) The compound in step i) is sulfated or sulfonated and then neutralized with a base selected from the group consisting of sodium hydroxide or potassium hydroxide, ammonia, amines, and amino alcohols. To obtain the compound according to claims 1 to 5, wherein R2 is or , where M, m and the dashed line are as defined in claim 1.

7. The method according to claim 6, wherein, The acidic catalyst is selected from the group consisting of: alkylbenzene sulfonic acid, methanesulfonic acid, sulfuric acid, phosphoric acid, hypophosphoric acid, and hydrochloric acid.

8. The method according to claim 6 or 7, wherein, (i) R3 is a C10 to C17 alkyl or C10 to C17 alkenyl, preferably a C10 to C17 alkyl; and (ii) R4 is hydrogen.

9. The method according to any one of claims 6 to 8, wherein, This straight-chain triol contains 4 to 6 carbon atoms.

10. The method according to any one of claims 6 to 9, wherein, The sulfation step includes i) Sulfation with sulfur trioxide in a falling film reactor; ii) Sulfate with chlorosulfuric acid; or iii) Sulfate with aminosulfonic acid in the presence of urea.

11. The use of the compound according to any one of claims 1 to 5 in cleaning compositions, in fabric and household care products, in cosmetic formulations, as a crude oil demulsifier, as a surfactant in enhanced oil recovery, as a surfactant in corn oil separation, as a surfactant in fermentation processes, as a surfactant in mineral ore flotation, in pigment dispersions for inkjet inks, in formulations for electroplating, in adhesive compositions, and as a dispersant for agricultural chemical formulations.

12. The use according to claim 11, wherein it is used in cleaning compositions and / or in fabric and household care products, preferably in cleaning compositions. i) Improved removal of oily / greasy stains, and / or ii) Improved sebum removal, and / or iii) Clay removal, and / or iv) Removal of particulate stains, and / or v) Dispersion and / or emulsification of dirt, and / or vi) Modification of the treated surface to improve the removal of subsequent contamination, and / or vii) Whiteness improvement and / or Preferably used in cleaning compositions for the removal of oily / greasy stains. Each of the preceding options i) to vii) is preferably used in laundry detergent formulations and / or detergent formulations for hand-washing dishes and / or formulations suitable for (pre)treating textiles and / or soap bars, more preferably in liquid laundry detergent formulations and / or liquid detergent formulations for hand-washing dishes.

13. Cleaning compositions, fabric and household care products, industrial and institutional cleaning products, cosmetic formulations, crude oil demulsifiers, petroleum recovery formulations, formulations for corn oil separation, formulations for fermentation processes, flotation agents for mineral ores, pigment dispersions for inkjet inks, formulations for electroplating, adhesive compositions, dispersants for agricultural chemical formulations, comprising at least one compound according to any one of claims 1 to 5, preferably cleaning compositions and / or fabric and household care products and / or industrial and institutional cleaning products comprising at least one compound according to any one of claims 1 to 5.

14. The cleaning composition of claim 13, further comprising: i) at least one cleaning polymer or stain-removing polymer, and / or ii) at least one additional surfactant selected from the group consisting of anionic surfactants and / or nonionic surfactants and / or amphoteric surfactants and / or amphoteric surfactants and / or cationic surfactants, and / or iii) An antimicrobial agent selected from the group consisting of 2-phenoxyethanol and 4,4'-dichloro-2-hydroxydiphenyl ether; preferably comprising 2-phenoxyethanol in an amount ranging from 2 ppm to 5% by weight of the composition; more preferably comprising 0.1% to 2% phenoxyethanol or preferably comprising 0.001% to 3%, more preferably 0.002% to 1%, or even more preferably 0.01% to 0.6% of 4,4'-dichloro-2-hydroxydiphenyl ether, each by weight of the composition, and / or iv) At least one enzyme selected from the list consisting of lipases, hydrolases, amylases, DNases, proteases, cellulases, hemicellulases, phospholipases, esterases, mannanases, xylanases, dispersases, oxidoreductases, cutinases, pectinases, pectinases, lactases, and peroxidases, and combinations of at least two of the foregoing types, preferably selected from one or more lipases, hydrolases, amylases, proteases, cellulases, and combinations of at least two of the foregoing types, more preferably at least one enzyme selected from proteases, and / or v) At least one compound selected from the group consisting of detergent builders, co-builders, structuring agents or thickeners, clay stain removers / anti-redeposition agents, polymer detergents, dispersants such as polymer dispersants, polymer grease cleaners, solubilizers, chelating agents, enzymes, enzyme stabilizers, bleaching compounds, bleaching agents, bleaching activators, bleaching catalysts, brighteners, odor control agents, pigments, dyes, opacifiers, colorants, dye transfer inhibitors, chelating agents, foaming agents, foam inhibitors (defoamers), stain removers, silver care agents, anti-tarnish agents and / or preservatives, alkalinity sources, pH adjusters, pH buffers, water-soluble aids, detergent particles, antibacterial agents, antioxidants, softeners, carriers, processing aids, fragrance precursors, dye fixatives, and fragrances. vi) A cosolvent selected from the group consisting of aliphatic alcohols, diols (preferably propylene glycol), or triols containing 2 to 5 carbon atoms, or from the group consisting of ethylene glycol or diethylene glycol monoalkyl ethers containing 2 to 5 carbon atoms in the alkyl portion, or from the group consisting of propylene glycol or dipropylene glycol monoalkyl ethers containing 2 to 5 carbon atoms in the alkyl portion, and / or vii) Water.

15. A cleaning method comprising bringing the cleaning composition of claim 13 or 14 into contact with an object, preferably clothing or hard-surface household item, that needs to be cleaned.

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