Alkyl polyglycerol amine quaternary ammonium salt surfactants and their use in cleaning applications

Abstract

A polyglycerol quaternary ammonium compound having formula (I): wherein R represents a C8-30 aliphatic group; each R1 independently represents a C1-8 aliphatic group; each Gly each independently represents a polyglyceryl moiety having 7 to 20 glycerol units; m represents 1 or 2; n represents 1 or 2; m + n = 3; and X-represents a counter anion. Also disclosed are methods of making the compounds of formula (I), aqueous cleaning compositions comprising the compounds of formula (I), and methods of cleaning an object to be cleaned using the cleaning compositions. (I)

Description

TECHNICAL FIELD

[0001] The present disclosure relates to alkyl polyglycerin amine quaternary ammonium salt surfactants and their use in cleaning applications. BACKGROUND

[0002] Surfaces are prone to contamination with oily substances, such as petroleum-based chemicals (e.g., motor oil) and bio-based materials (e.g., kitchen grease). To clean greasy surfaces, a number of solvents can be used, such as hydrocarbons, d-limonene, and butyl acetate. However, to achieve good cleaning results often requires large amounts of solvent, and thus is not cost-effective. In addition, solvents can be volatile (volatile organic compound (VOC) issues) or flammable. They can also leave residues on the surface (when low-volatility solvents are used).

[0003] Water-based degreasing formulations have advantages over solvent-based degreasing formulations. Water-based degreasing formulations typically contain two main components in addition to water - a degreaser and a hydrotrope. The degreaser is the main ingredient that does the work of degreasing, while the hydrotrope maintains and stabilizes the degreaser in the water environment. A common degreaser is a short-chain alcohol ethoxylate, such as Berol® 360 (alcohol ethoxylate) available from Nouryon. A common hydrotrope is an ethoxylated quaternary ammonium salt surfactant, such as Berol® R648 NG (alkyl amine ethoxylate methyl chloride quaternary ammonium salt) also available from Nouryon.

[0004] The choice of hydrotrope can be important. Water-based degreasing formulations containing alcohol ethoxylate but without the addition of a hydrotrope can appear hazy. However, the addition of a good hydrotrope to such formulations can clarify the hazy solution. In addition to the effectiveness and efficiency of its hydrotropic ability, an ideal hydrotrope should contribute to some extent to the degreasing. Typical degreasing formulations on the market are able to form clear aqueous solutions over a wide range of concentrations (about 0.1% to 10% active). Lower concentrations of the degreasing formulation are used for general degreasing applications, while higher concentrations of the degreasing formulation are used for heavy-duty applications.

[0005] However, while alkyl amine ethoxylate methyl chloride quaternary ammonium salts perform well, they have drawbacks. Cleaning formulations containing such materials cannot be called “dioxane-free” because they are produced with ethylene oxide, which produces the byproduct 1,4-dioxane during the chemical reaction. In addition, ethylene oxide is not bio-based.

[0006] It is an object of the present disclosure to provide new co-solvents that show similar or even superior co-solubilizing power to the corresponding ethoxylate co-solvents, however the formulations containing these new co-solvents do not lose degreasing performance and at the same time are free of dioxane and are bio-based.

[0007] U.S. Patent No. 4,994,199 describes amine glycidol compounds having the formula:

[0008] wherein R is C8-18alkyl; R 1 is benzyl or Ci-8alkyl; X is CI, Br, or I; and n and m are each 1 to 6.

[0009] These compounds are described as being useful as antimicrobial agents in cleaning compositions. The three cocoamine quaternary ammonium glycidol having m + n = 2, 3, and 4 have “significant” antibacterial and antifungal activity, while octadecylamine quaternary ammonium glycidols having m + n = 4 and 12 tested by the same method generally do not have the same properties, thus implying that the activity of the latter compounds is not significant.

[0010] These compounds are not described as functioning as co-solvents. SUMMARY

[0011] The present disclosure meets these and other objects, in one embodiment, the present disclosure relates to a polyglyceryl quaternary ammonium compound having the following formula (I): (I) wherein R represents a C8-30aliphatic group; R 1 each independently represents a Ci-8aliphatic group; each Gly independently represents a polyglyceryl moiety having 7 to 30 glycerol units; m represents 1 or 2; n represents 1 or 2; m + n = 3; and X - represents a counter anion.

[0012] The present disclosure relates, in a second embodiment, to a method of making a compound of formula (I), the method comprising: (a) reacting at least one primary or secondary amine with glycidol to obtain a polyglyceryl amine; and (b) quaternizing the polyglyceryl amine to obtain a polyglycerol quaternary ammonium compound having the formula (I).

[0013] The present disclosure relates in a third embodiment to an aqueous cleaning composition comprising: (a) at least one compound of formula (I) as described herein; and (b) water.

[0014] The present disclosure relates in yet another embodiment to a method of cleaning an object to be cleaned, the method comprising contacting said object with an aqueous cleaning composition as described herein. BRIEF DESCRIPTION OF DRAWINGS

[0015] The present disclosure will now be described in more detail with reference to the accompanying drawings, in which: Figure 1 is a schematic representation depicting the cleaning ability of the co-solvents of Examples 2 and 3 and the "control" (BEROL® R648 NG) on a panel soiled with engine grease in the presence of 2% NaOH. DETAILED DESCRIPTION

[0016] The following detailed description is merely exemplary in nature and is not intended to limit the disclosure or the application and uses of the subject matter described herein. Furthermore, there is no intention to be bound by any theory presented in the preceding background or the following detailed description. Also, it should be understood that throughout this application, where various embodiments have been presented in terms of certain examples, all numerical values provided herein, except actual example values, are approximations only and should be understood to be "about" or "approximately" the recited value.

[0017] In one typical embodiment, in the compound of formula (I), m represents 2 and n represents 1, the compound having the structure of formula (II): (II) wherein the two "R 1 " groups are the same or different; and the other variables are as described above.

[0018] In another typical embodiment, in the compound of formula (I), m represents 1 and n represents 2, the compound having the structure of formula (III): (III) wherein the two "Gly" groups are the same or different; and the other variables have the meaning given above.

[0019] The term "glyceryl" as used herein means a group derived from glycerol.

[0020] In any of the above embodiments, R is a linear or branched, saturated or unsaturated C8-30 aliphatic group, typically a C8-22 aliphatic group, most typically a C10-18 aliphatic group. In various non-limiting embodiments, all numerical values (integers and decimals) and numerical ranges, including the above-noted values and values falling between the above-noted values, are expressly contemplated for use herein.

[0021] In more typical embodiments, R represents, for example, a heptyl, octyl, nonyl, decyl, undecyl, dodecyl, or coco or lauryl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, or stearyl (tallow or soy) group, and mixtures thereof.

[0022] In most typical embodiments, R represents a fatty linear or branched, saturated or unsaturated alkyl group having 12 or 14 carbon atoms.

[0023] Also, each R 1 group is each independently a C1-8 aliphatic group, typically a C1-4 aliphatic group, most typically a methyl or ethyl group. In various non-limiting embodiments, all numerical values (integers and decimals) and numerical ranges, including the above-noted values and values falling between the above-noted values, are expressly contemplated for use herein.

[0024] Each Gly group is each independently a polyglyceryl moiety having 7 to 20 glycerol units, typically a polyglyceryl moiety having 7 to 15 glycerol units, most typically a polyglyceryl moiety having 7 to 12 glycerol units. In various non-limiting embodiments, all numerical values (integers and decimals) and numerical ranges, including the above-noted values and values falling between the above-noted values, are expressly contemplated for use herein.

[0025] Further, the polyglyceryl chain can be linear, branched, or cyclic. For example, a linear polyglyceryl chain can comprise Formula (IV): (IV) A branched polyglyceryl chain can comprise Formula (V): (V) A cyclic polyglyceryl chain can comprise Formula (VI): (VI); or Formula (VII): (VII).

[0026] In some embodiments, the polyglyceryl moiety can be a combination of branched, linear, and / or cyclic segments.

[0027] Extension of the polyglyceryl moiety can be from the terminal primary hydroxyl group of a glycerol residue (yielding a linear segment), or from a non-terminal secondary hydroxyl group of a glycerol residue (yielding a branched segment).

[0028] Counterion X - may be any suitable anion. In typical embodiments, X - is a counterion selected from halide (halogen), salicylate, carbonate, or alkyl sulfate, in particular methyl sulfate.

[0029] The new co-solvents exhibit excellent co-solubilizing power. Moreover, as they are prepared using glycidol, the new co-solvents are dioxane-free and bio-based.

[0030] Reaction conditions for reacting an alkyl amine with glycidol are well known in the art. Typically, the reaction is carried out at a temperature of about 65 °C to about 165 °C, with or without a nitrogen atmosphere. The reaction can be carried out without a catalyst, or can be carried out in the presence of a base catalyst such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methoxide, potassium methoxide, and the like.

[0031] Reaction conditions for the quaternization of the polyglyceryl amine are similar to the well-known quaternization conditions for alkyl amine alkoxylates. For example, the quaternization of the polyglyceryl amine with an alkyl chloride (e.g., methyl chloride) or a dialkyl sulfate (e.g., dimethyl sulfate) can be carried out in a sealed reactor at a temperature below 110 °C. The reaction can be carried out without a catalyst. A solvent such as water, a diol, or an alcohol can be used to reduce the viscosity of the product.

[0032] The cleaning formulations containing the compounds disclosed herein can be used for a variety of cleaning purposes, for example, they can be formulated for household cleaning, industrial cleaning, all-purpose cleaning, car washing, acidic and alkaline cleaning, deck and floor cleaning, hard surface cleaning, metal cleaning, food and beverage cleaning, automatic and manual dishwashing, laundry detergents, and the like.

[0033] To this end, the cleaning formulations can include, in addition to the disclosed compound of formula (I) and water, other conventional ingredients well known in the cleaning art.

[0034] In typical embodiments, the cleaning composition comprises one or more non-ionic surfactants.

[0035] In more typical embodiments, the one or more nonionic surfactants are selected from the group consisting of nonionic alkylene oxide adducts, in particular C8-C18-linear and branched alcohols (alcohol alkoxylates) and amine alkoxylates comprising 1 to 20 ethylene oxide units and 0 to 5 propylene oxide units. Nonionic alkyl polyglyceryl ethers prepared using C8-C18-linear and branched alcohols and 1 to 10 glycidol units, or alkyl polyglyceryl amines prepared using C8-C18-linear and branched alkyl amines and 1 to 10 glycidol units can also be used.

[0036] Nonionic alkylene oxide adducts are well-known conventional products, wherein the molecule comprises a hydrophobic part and a part comprising alkylene oxide units, the latter part having hydrophilic properties. Thus, the present disclosure relates to the use of a compound of formula (I) as a solubilizer for nonionic surfactants in aqueous solutions. In other words, the present disclosure relates to the improved solubilization of nonionic surfactants to manufacture compositions with good cleaning performance, wherein water, nonionic surfactant, a compound of formula (I) as defined above, and other optional ingredients are combined and / or mixed in one or several steps.

[0037] Suitably, the content of each component is: a) alcohol alkoxylate at least 0.05 wt.%, typically at least 0.5 wt.%, and at most 20 wt.%, typically at most 15 wt.%, most typically at most 10 wt.%, b) compound of formula (I) at least 0.02 wt.%, typically at least 0.1 wt.%, and at most 20 wt.%, typically at most 15 wt.%, most typically at most 10 wt.%, and c) alkali metal hydroxide, alkaline builder and / or alkaline complexing agent 0 wt.%, typically at least 0.05 wt.%, and at most 30 wt.%, typically at most 20 wt.%, more typically at most 15 wt.%, most typically at most 10 wt.%. b) compound of formula (I) at least 0.02 wt.%, typically at least 0.1 wt.%, and at most 20 wt.%, typically at most 15 wt.%, most typically at most 10 wt.%, and c) alkali metal hydroxide, alkaline builder and / or alkaline complexing agent 0 wt.%, typically at least 0.05 wt.%, and at most 30 wt.%, typically at most 20 wt.%, more typically at most 15 wt.%, most typically at most 10 wt.%. c) alkali metal hydroxide, alkaline builder and / or alkaline complexing agent 0 wt.%, typically at least 0.05 wt.%, and at most 30 wt.%, typically at most 20 wt.%, more typically at most 15 wt.%, most typically at most 10 wt.%.

[0038] It is particularly typical that the composition comprises alkali metal hydroxide, alkaline builder and / or alkaline complexing agent.

[0039] The nonionic surfactant typically has the following formula: R3O-(PO)x(EO)y(PO)zH (II) where R3 is a C8 to C18 linear or branched chain alkyl, typically C8 to C12; PO is a propylene oxide unit, EO is an ethylene oxide unit, x = 0 - 5, typically 0-4, most typically 0-2; y = 1-20, typically 1-12, more typically 2-8, most typically 2-5; and z = 0 - 5, typically 0-4, more typically 0-2, most typically 0. Thus, in addition to 1-20 ethylene oxide units, the C8-C18-alcohol alkoxylate can also contain up to 5 propylene oxide units. When propylene oxide units are present, the number can be as little as 0.1 moles of PO per mole of alcohol. The ethylene oxide units and propylene oxide units can be added randomly or in blocks. The blocks can be added in any order to the alcohol. The alkoxylate can also contain an alkyl group having 1-4 carbon atoms at the terminal position. Typically, the alkoxylate contains 2-8 ethylene oxide units and 0-2 propylene oxide units. The alkyl group of the nonionic surfactant can be linear or branched, saturated or unsaturated. Suitable linear nonionic surfactants are C9-C11 alcohol + 4, 5, 6, 7, or 8 moles of EO, C8-C10 alcohol + 3, 4, 5, 6, 7, or 8 moles of EO, C12-C14 alcohol + 3, 4, 5, 6, 7, or 8 moles of EO, and C10-C14 alcohol + 8 moles of EO + 2 moles of PO. Suitable branched nonionic surfactants are 2-ethylhexanol + 3, 4, or 5 moles of EO, 2-ethylhexanol + 2 moles of PO + 4, 5, or 6 moles of EO, 2-propylheptanol + 3, 4, 5, or 6 moles of EO, and 2-propylheptanol + 1 mole of PO + 4 moles of EO, C9 or C11 alcohol + 4, 5, 6, 7, or 8 moles of EO, tridecanol + 4, 5, 6, 7, or 8 moles of EO. Another example is 2-butyloctanol + 5, 6, or 7 moles of EO. Whenever the degree of alkoxylation is discussed, these numbers represent the molar average.

[0040] The composition can be acidic, neutral, or basic. Basic compositions are typically based on alkali metal hydroxides, alkaline builders, and / or complexing agents (sequestering agents). Basic compositions are especially typical.

[0041] The alkali metal hydroxide is typically sodium hydroxide or potassium hydroxide. The alkaline builder can be an alkali metal carbonate or an alkali metal bicarbonate, such as sodium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate, an alkali metal silicate, such as sodium silicate or sodium metasilicate, or an alkali metal phosphate, such as sodium orthophosphate. Alkaline builders that act by complexation are, for example, sodium pyrophosphate and sodium tripolyphosphate, and the corresponding potassium salts. The builder / complexing agent can also be organic. Examples of organic builders / complexing agents are aminocarboxylic acid salts, such as glutamic acid Ν,Ν-diacetate (GLDA), methylglycine Ν,Ν-diacetate (MGDA), trisodium nitrilotriacetate (Na3NTA), sodium ethylenediaminetetraacetate (EDTA), sodium diethylenetriaminepentaacetate, sodium 1,3- propanediaminetetraacetate and sodium hydroxyethylethylenediaminetriacetate; aminopolym phosphonic acid salts, such as nitrilotrimethylene phosphonic acid salt; organic phosphates; polycarboxylic acid salts, such as citric acid salts; and alkali metal salts of gluconic acid, such as sodium or potassium gluconate.

[0042] In neutral and acidic compositions, complexing agents and / or pH adjusting agents, such as citric acid, oxalic acid, acetic acid, sulfamic acid, hydrochloric acid, can also be added.

[0043] In another typical embodiment, the cleaning composition comprises one or more chelating agents.

[0044] In one embodiment, the chelating agent is at least one aminocarboxylate chelating agent selected from the group consisting of methylglycinediacetic acid (MGDA), N,N-dicarboxymethyl glutamic acid (GLDA), N-hydroxyethyliminodiacetic acid, nitrilotriacetic acid (NTA), ethylenediaminetetraacetic acid (EDTA), N-hydroxyethylethylenediaminetriacetic acid (HEDTA), diethylenetriaminepentaacetic acid (DTPA), ethylenediaminetetrapropionic acid, triethylenetetraminehexaacetic acid (TTHA), tetraacetylethylenediamine (TAED), iminodisuccinic acid (IDS), ethanoldiglycine (EDG), and the alkali metal, ammonium and substituted ammonium salts of each thereof. In a particularly typical embodiment, the aminocarboxylate chelating agent is selected from the group consisting of: EDTA, GLDA, MGDA, salts thereof, and combinations thereof.

[0045] In another embodiment, the chelating agent is a non-aminocarboxylate chelating agent that does not contain a nitrogen atom but does contain a carboxylate functional group. In a typical embodiment, the non-aminocarboxylate chelating agent is a di- or higher valent carboxylic acid. In a particularly typical embodiment, the non-aminocarboxylate chelating agent is at least one member selected from the group consisting of: citric acid, isocitric acid, 2,3-hydroxycitric acid, tricarboxypropanoic acid, ethanetristearboxylic acid (HETA), aconitic acid, succinic acid, maleic acid, fumaric acid, oxaloacetic acid, ketoglutaric acid, butanetetraearboxylic acid, polycarboxylic acids, and the alkali metal, ammonium and substituted ammonium salts of each thereof. In a particularly typical embodiment, the non-aminocarboxylate chelating agent is selected from the group consisting of: citric acid and salts thereof.

[0046] When one or more chelating agents are present in the formulation, they are present at a total chelating agent level of greater than 0 wt%, typically at least 0.05 wt%, most typically at least 1 wt%, and up to 30 wt%, typically up to 20 wt%, more typically up to 15 wt%, most typically up to 10 wt%.

[0047] In another typical embodiment, in addition to one or more nonionic surfactants and / or chelating agents, the cleaning composition comprises one or more adjunct ingredients selected from: aesthetic agents, anti- filming agents, anti-redeposition agents, anti-spotting agents, anti- graying agents, beads, binders, biocides, bleach activators, bleach catalysts, bleach stabilizing systems, bleaches, brighteners, buffers, builders, carriers, clays, color speckles, controlled release agents, corrosion inhibitors, dish care agents, disinfectants, dispersants, drain line opening agents, drying agents, dyes, dye transfer inhibitors, enzymes, enzyme stabilizing systems, fillers, free radical inhibitors, fungicides, germicides, hydrotropes other than the compound of Formula (I), opacifiers, perfumes, pH adjusting agents, pigments, processing aids, silicates, soil release agents, suds suppressors, anionic surfactants, cationic surfactants, stabilizers, thickeners, zeolites, and mixtures thereof.

[0048] When one or more adjunct ingredients are present in the formulation, they are present at a total adjunct ingredient level of greater than 0 wt%, typically at least 0.05 wt%, most typically at least 1 wt%, and up to 30 wt%, typically up to 20 wt%, more typically up to 15 wt%, most typically up to 10 wt%.

[0049] The present disclosure encompasses both dilute and concentrated compositions.

[0050] The dilute compositions of the present disclosure are clear and stable. The clear interval is suitably between 0-40°C, typically between 0-50°C, most typically between 0-60°C. This can be adjusted by varying the ratio of hydrotrope to nonionic surfactant. The dilute compositions typically comprise at least 80 wt%, suitably at least 90 wt% water, and typically up to 99.5 wt%, suitably up to 98 wt% water.

[0051] The concentrated compositions of the present disclosure are clear and stable. The clear interval is suitably between 0-40°C, typically between 0-50°C, most typically between 0-60°C. This can be adjusted by varying the ratio of hydrotrope to nonionic surfactant. The concentrates typically comprise at least 50 wt%, suitably at least 70 wt% water, and typically up to 95 wt%, suitably up to 90 wt% water.

[0052] There are several advantages to using the compounds of Formula (I) as co-solvents for nonionic surfactants. First, they are excellent co-solvents while also contributing to the cleaning performance of the composition. Their cleaning efficiency is very good even in the case of highly diluted compositions. Furthermore, their biodegradability is expected to be superior to previously known compounds, such as BEROL® R648 NG (Nouryon) used in hard surface cleaning compositions.

[0053] The present disclosure will now be described in more detail with reference to the following non-limiting examples. Examples

[0054] Example 1

[0055] A. Preparation of alkyl polyglyceryl amines The preparation of alkyl polyglyceryl amines is known, for example, see U.S. Pre-Grant Publication No. 2022 / 0039378, the entirety of which is incorporated herein by reference.

[0056] Raw materials used Tallow amine Armeen™-97 (AkzoNobel) Oleyl amine Armeen OM-97 (AkzoNobel) Cocoalkyl amine Armeen CD (AkzoNobel) Glycidol (Acros) Abbreviations used “T” stands for “tallow amine”; “O” stands for “oleyl amine”; “C” stands for “cocoalkyl amine”; “G” stands for “glyceryl unit”; “Q” stands for quaternized with methyl chloride.

[0057] For example: T-5G (i.e., tallow amine-5G) indicates a tallow amine with 5 glyceryl units.

[0058] O-8G (i.e., oleyl amine-8G) indicates an oleyl amine with 8 glyceryl units.

[0059] C-20G (i.e., cocoalkyl amine-20G) indicates a cocoalkyl amine with 20 glyceryl units. Table 1

[0060]

[0061] Synthesis steps For illustrative purposes only, Sample #1 in Table 1 (T-5G species outside the scope of the claims of this application) was prepared using the following procedure, and other unquaternized samples were synthesized using similar procedures, with the appropriate adjustment of the molar ratio of the relevant fatty acid amine to glycidol (as described below).

[0062] Glycidol (44.4 g, 0.6 mol) was added dropwise over 3 hours to tallow amine (32.04 g, 0.12 mol) stirred in a round bottom flask under a nitrogen atmosphere, maintaining the reaction mixture temperature between 80° and 120° C. The reaction mixture was further stirred at about 110° C for about an hour until IR analysis showed no more epoxy peak at about 840 cm-1 from the glycidol. The clear, light brown viscous liquid product thus obtained was collected.

[0063] For Samples #2-#5, the procedure of Sample #1 was repeated using the specified amine with glycidol in the relevant molar ratio. For example, for Sample #2, the procedure of Sample #1 was repeated with a molar ratio of tallow amine to glycidol of 1:10, a molar ratio of oleyl amine to glycidol of 1:8 in Sample #3, and so on.

[0064] B. Quaternization Unquaternized Samples 1-5 can be quaternized by charging about 1 milliequivalent / g of unquaternized sample and water into a 2L titanium autoclave, deoxygenating the contents by pressurizing with N2 to 60 psig and venting multiple times. Methyl chloride is added, but in minimal excess to avoid hydrolysis. The quaternization process is monitored by periodically sampling, measuring pH, and titrating for free amine. When the free amine measurement is less than 5% of the starting amine, the reaction can be cooled and purged with nitrogen. The contents can be collected without filtration, and water removed using a rotary evaporator until the solution becomes viscous.

[0065] Example 2 Similar to Example 1, products with 9 glycerol units can be prepared starting from C12-C14-alkyl(methyl)amines. Methods for preparing secondary amines are generally known; see, for example, US 9,000,218.

[0066] Example 3 Similar to Example 1, products with 12 glycerol units can be prepared starting from C12-C14-alkyl(methyl)amines.

[0067] Example 4 Similar to Example 1, additional cosolvent products can be prepared from the specified amines by introducing the specified number of glycerol units, as shown in Table 2: Table 2

[0068]

[0069] Example 5 BEROL® R648 NG (Noligen) is the market leading product in cleaning formulations, providing top cleaning performance, derived from renewable plant sources, and is environmentally persistent and ecotoxicity low or none. Although BEROL® R648 NG is readily biodegradable, it has certain drawbacks, for example, it is an ethoxylate (not dioxane free) and has a low RCI (Renewable Carbon Index). With the rapid changes in regulations and environmental awareness, there is an urgent need for a product that is ethylene oxide free (and dioxane free), has a higher RCI (typically > 50%) and has as good performance as BEROL® R648 NG.

[0070] The co-solvents of the present disclosure meet all the above criteria and have as good performance as the benchmark BEROL® R648 NG. The co-solvents of the present disclosure are dioxane free and are bio-based, as the glycerol units are derived from glycidol, which is bio-based. Furthermore, some of the co-solvents of the present disclosure can be readily biodegradable, have a high RCI and low / no toxicity. At the same time, they exhibit as good cleaning performance as the benchmark BEROL® R648 NG.

[0071] The co-solvents of Examples 2 and 3, prepared differently, exhibit the ability to solubilize BEROL® 260 (an alcohol ethoxylate) and DISSOLVINE® GL-47-S (glutamic acid, N,N-diacetic acid, tetrasodium salt), generating stable formulations at room temperature, as shown in the following table in comparison to BEROL® R648 NG: Table 3

[0072]

[0073] The degreasing effect of the test formulations was then evaluated on white painted metal panels uniformly coated with difficult-to-clean greasy dirt collected from a train engine. Application was performed simply by pouring the cleaning formulation (1:20 dilution in water) onto the surface (non-mechanical cleaning). After a short time interval, the entire panel was rinsed with tap water and a quantitative evaluation of the cleaning performance was made. The results are shown in the following table and are depicted in Figure 1 Figure 1. The cleaning performance of the co-solvents of Examples 2 and 3 shows good prospects compared to the control.

[0074] While the disclosure has been described above by reference to particular implementations, alternatives, modifications, and other variations will be apparent to those skilled in the art. All such alternatives, modifications and variations are intended to fall within the spirit and scope of the present disclosure.

Claims

1. Polyglycerol quaternary ammonium compounds of formula (I): (I) in R represents a C8-30 aliphatic group; R 1 Each group independently represents a C1-8 aliphatic group; Gly represents a polyglycerol moiety having 7 to 20 glycerol units; m represents 1 or 2; n represents 1 or 2; m + n = 3; and X - It indicates resistance to anions.

2. The compound according to claim 1, wherein m represents 2, n represents 1, and the compound has the structure of formula (II): (II) in Two Rs 1 The groups may be the same as or different from each other.

3. The compound according to claim 1, wherein m represents 1, n represents 2, and the compound has the structure of formula (III): (III) in The two Gly groups may be the same as or different from each other.

4. The compound according to any one of the preceding claims, wherein R is a C8-22 aliphatic group.

5. The compound according to claim 4, wherein R is a C10-18 aliphatic group.

6. The compound according to claim 5, wherein R is an aliphatic straight-chain or branched, saturated or unsaturated alkyl group having 12 or 14 carbon atoms.

7. The compound according to any one of the preceding claims, wherein each R 1 Each is an independent C1-4 aliphatic group.

8. The compound according to claim 7, wherein R 1 It is methyl or ethyl.

9. The compound according to any one of the preceding claims, wherein each Gly group is independently a polyglycerol moiety having 7 to 15 glycerol units.

10. The compound of claim 9, wherein each Gly group is independently a polyglycerol moiety having 7 to 12 glycerol units.

11. The compound of claim 10, wherein at least one Gly group is selected from a glycerol chain, said glycerol chain comprising a structure selected from: ； ； ;and 。 12. The compound according to any one of the preceding claims, wherein X - It is selected from the following counterions: halides, salicylates, carbonates and alkyl sulfates.

13. The compound according to claim 12, wherein X - It is methyl sulfate.

14. A method for preparing a polyglycerol quaternary ammonium compound of formula (I) according to any one of claims 1-13, the method comprising: (a) Reacting at least one primary or secondary amine with glycidyl glycerol to obtain a polyglycerol-based amine; and (b) Quaternize the polyglycerol-based amine to obtain the polyglycerol quaternary ammonium compound of formula (I).

15. A water-based cleaning composition comprising: (a) at least one polyglycerol quaternary ammonium compound of formula (I) according to any one of claims 1-13; and (b) Water.

16. A method for cleaning an object to be cleaned, the method comprising contacting the object with the aqueous cleaning composition according to claim 15.

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