Alkyl polyglycerylamine quaternary surfactants and use thereof in cleaning applications

Abstract

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

Description

ALKYL POLYGLYCERYLAMINE QUATERNARY SURFACTANTS AND USE THEREOF IN CLEANING APPLICATIONSFIELD OF THE DISCLOSURE

[0001] The present disclosure relates to alkyl polyglycerylamine quaternary surfactants and their use in cleaning applications.BACKGROUND

[0002] Surfaces can be easily contaminated by oily substances such as petroleumbased chemicals (e.g., engine greases) and biobased materials (e.g., kitchen greases). To clean a greasy surface, many solvents can be used such as hydrocarbons, d-limonene, and butyl acetate. However, doing a good cleaning job typically requires a large amount of solvents, hence, it is not cost-effective. In addition, the solvents may be volatile (VOC issue) or flammable. They may also leave residuals on surfaces (when low volatility solvents are used).

[0003] Aqueous-based degreasing formulations have advantages over the solventbased degreasing formulations. Aqueous degreasing formulations typically include, in addition to water, two main components - a degreaser and a hydrotrope. The degreaser is the main ingredient that does the degreasing job while the hydrotrope maintains and stabilizes the degreaser in an aqueous 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 surfactant such as Berol® R648 NG (alkylamine ethoxylate methyl chloride quat) also available from Nouryon.

[0004] The selection of the hydrotrope can be important. Aqueous degreasing formulations containing alcohol ethoxylate without the hydrotrope can be hazy in appearance. However, the addition of a good hydrotrope to such a formulation can turn the hazy solution clear. In addition to its effectiveness and efficiency in terms of hydrotroping power, the hydrotrope should ideally also contribute to the degreasing to certain extent. A typical degreasing formulation on the market can form clear aqueous solutions in a wide concentration range (~0.1 to 10% active). The degreasing formulations with lower concentrations are for general degreasing use while the degreasing formulations with higher concentrations are for heavy duty use.

[0005] However, despite their good performance, the alkylamine ethoxylate methyl chloride quats have drawbacks. Cleaning formulations containing such substances cannot be called “dioxane-free” because they are made using ethylene oxide which generates 1,4-dioxane as a by-product during the chemical reaction. In addition, the ethylene oxide is not biobased.

[0006] It is an object of the present disclosure to provide new hydrotropes that show similar or even superior hydrotroping power to the corresponding ethoxylate hydrotropes yet formulations containing the new hydrotropes do not suffer a loss of degreasing performance but, nevertheless, are dioxane-free and biobased.

[0007] U.S. Patent No. 4,994,199 describes amine glycidol compounds of the formula:whereR is C8- 18 alkyl;R1is benzyl or C 1-8 alkyl;X is Cl, Br, or I; and n and m are each from 1 to 6.

[0008] These compounds are described as being useful as antimicrobial agents in cleaning compositions. Three cocoamine quaternary glycidols having m + n = 2, 3, and 4 can have “significant” antibacterial and antifungal activity, whereas octadecylamine quaternary glycidols having m + n = 4 and 12 tested in the same manner typically do not have that same characteristic, thereby implying the activity of these latter compounds is insignificant.

[0009] The compounds are not described as functioning as hydrotropes.BRIEF SUMMARY

[0010] These and other objects are met with the present disclosure, which relates in one embodiment to a polyglycerol quaternary compound of the formula (I):R1mR - N- - (Gly)nX-(I)whereinR represents a C8-30 aliphatic group;R1independently represents a Cl-8 aliphatic group;Gly independently represents a polyglyceryl moiety having 7 to 30 glyceryl units; m represents 1 or 2; n represents 1 or 2; m + n = 3; andX- represents a counteranion.

[0011] The present disclosure relates in a second embodiment to a process of preparing a compound of formula (I) comprising:(a) reacting at least one primary or secondary amine with glycidol to yield a polyglyceryl amine; and(b) quatemizing the polyglycerol amine to yield a polyglycerol quaternary compound of the formula (I).

[0012] 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.

[0013] The present disclosure relates in yet another embodiment to a method of cleaning an object to be cleaned comprising contacting the object with an aqueous cleaning composition as described herein.BRIEF DESCRIPTION OF THE DRAWINGS

[0014] The disclosure will now be described in greater detail with reference to the drawings, wherein:

[0015] Fig. 1 is an illustration depicting the cleaning power of the hydrotropes of Examples 2 and 3 versus the “Control” (BEROL® R648 NG) in the presence of 2% NaOH on a plate soiled with engine grease.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 as described herein. Furthermore, there is no intention to be bound by any theory presented in the preceding background or the following detailed description. Moreover, it is contemplated that, in various non-limiting embodiments, it is to be appreciated that all numerical values as provided herein, save for the actual examples, are approximate values with endpoints or particular values intended to be read as “about” or “approximately” the value as recited.

[0017] In a typical embodiment, in the compound of formula (I), m represents 2 and n represents 1, and the compound has the structure of formula (II):R1R - N- - Gly X’R1(II) wherein the two “R1” groups are the same or different; and the other variables are as described hereinabove.

[0018] In another typical embodiment, in the compound of formula (I), m represents 1 and n represents 2, and the compound has the structure of formula (III): Gly X'(ill) wherein the two “Gly” groups are the same or different; and the other variables have the meanings given hereinabove.

[0019] The term “glyceryl” as used herein means a radical derived from glycerol.

[0020] In any of the aforementioned embodiments, R is a linear or branched, saturated or unsaturated C8-30 aliphatic group, typically C8-22 aliphatic, most typically CIO- 18 aliphatic. In various non-limiting embodiments, all values, both whole and fractional, and ranges of values, including and between those set forth above, are hereby expressly contemplated for use herein.

[0021] In a more typical embodiment, R represents, for example, heptyl, octyl, nonyl, decyl, nonadecyl, dodecyl, or coco or lauryl, tetra-decyl, pentadecyl, hexadecyl, heptadecyl, octadecyl or stearyl (tallow or soya), and mixtures thereof.

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

[0023] Likewise, each R1group is independently a Cl-8 aliphatic group, typically Cl -4 aliphatic, most typically methyl or ethyl. In various non-limiting embodiments, all values, both whole and fractional, and ranges of values, including and between those set forth above, are hereby expressly contemplated for use herein.

[0024] Each Gly group is independently a polyglyceryl moiety having 7 to 20 glyceryl units, typically a polyglyceryl moiety having 7 to 15 glyceryl units, most typically a polyglyceryl moiety having 7 to 12 glyceryl units. In various non-limiting embodiments, all values, both whole and fractional, and ranges of values, including and between those set forth above, are hereby expressly contemplated for use herein.

[0025] Also, the polyglyceryl chain can be linear, branched, or cyclic. For example, a linear polyglyceryl chain could comprise the formula (IV):

[0026] A branched polyglycerol chain could comprise the formula (V):

[0027] A cyclic polyglycerol chain could comprise the formula (VI):(VI); orthe formula (VII):(VII).

[0028] In some embodiments, the polyglyceryl moiety can be a combination of branched, linear, and / or cyclic segments.

[0029] Propagation of the polyglyceryl moiety can be from the terminal primary hydroxyl of a glyceryl residue (resulting in a linear segment), or from the non-terminal secondary hydroxyl of the glyceryl residue (resulting in a branched segment).

[0030] The counterion X" can be any suitable anion. In a typical embodiment, X- is a counterion selected from the group consisting of halides, salicylates, carbonates, or alkyl sulfates, particularly methyl sulfate.

[0031] The new hydrotropes exhibit excellent hydrotroping power. Moreover, because they are made using ethylene oxide, the new hydrotropes are dioxane-free and biobased.

[0032] Reaction conditions useful to react alkylamines with glycidol are well known in the art. Typically, the reaction proceeds at a temperature of from about 65°C to about 165°C with or without nitrogen atmosphere. Reaction can proceed without a catalyst or with a base catalyst such as for example, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methoxide, potassium methoxide etc.

[0033] Reaction conditions useful for the quatemization of polyglycerol amines are similar to the well-known quatemization condition of alkyl amine alkoxylates. For example, the quatemization of polyglycerol amines with alkyl chlorides, for example, methyl chloride, or dialkyl sulfates, for example, dimethyl sulfate, can proceed at a temperature below 110°C in a sealed reactor. Reaction can proceed without a catalyst. A solvent such as water, a glycol or alcohol can be used to reduce the viscosity of the product.

[0034] Cleaning formulations containing the disclosed compounds are useful for a variety of cleaning purposes, for example, they can be formulated for, household cleaning, industrial cleaning, all-purpose cleaning, car washing, acidic and caustic cleaning, deck and floorcleaning, hard surface cleaning, metal cleaning, food & beverage cleaning, automated and manual dishwash, laundry detergents and the like.

[0035] For such purposes, the cleaning formulations may include, in addition to the disclosed compounds of formula (I) and water, other conventional ingredients well known in the art of cleansing.

[0036] In a typical embodiment, the cleaning composition comprises one or more nonionic surfactants.

[0037] In a more typical embodiment, the one or more nonionic surfactants are selected from the group consisting of nonionic alkylene oxide adducts, especially C8-C18-linear and branched alcohol (alcohol alkoxylates) and amine alkoxylates comprising 1-20 ethyleneoxy units and 0-5 propyleneoxy units. The non-ionic alkyl polyglyceryl ethers made using C8-C18- linear and branched alcohol and 1-10 glycidol units or alkyl polyglycerylamines made using C8- C18-linear and branched alkyl amine and 1-10 glycidol units can also be used.

[0038] The nonionic alkylene oxide adducts are well known conventional products wherein the molecule comprises a hydrophobic moiety and a moiety containing alkyleneoxy units, said latter moiety having a hydrophilic character. Thus the disclosure relates to the use of compounds of formula (I) as hydrotropes for nonionic surfactants in aqueous solutions. In other words, the disclosure relates to the improved solubilization of nonionic surfactants to make compositions with a good cleaning performance wherein water, a nonionic surfactant, a compound having the formula (I) as defined above, and other optional ingredients are combined and / or mixed in one or several steps.

[0039] The amounts of the components are suitably: a) at least 0.05% by weight, typically at least 0.5% by weight, and at most 20% by weight, typically at most 15% by weight, and most typically at most 10% by weight, of alcohol alkoxylate, b) at least 0.02% by weight, typically at least 0.1% by weight, and at most 20% by weight, typically at most 15% by weight, and most typically at most 10% by weight, of compound of formula (I), and c) 0% by weight, typically at least 0.05% by weight, and at most 30% by weight, typically at most 20% by weight, more typically at most 15%by weight, and most typically at most 10% by weight, of alkali hydroxides, alkaline builders and / or alkaline complexing agents.

[0040] It is especially typical that the compositions include alkali hydroxides, alkaline builders and / or alkaline complexing agents.

[0041] The nonionic surfactants typically have the formula:R3O - (PO)x(EO)y(PO)zH (II) wherein R3 is a C8 to C18 linear or branched alkyl group, typically C8 to C12; PO is a propyleneoxy unit, EO is an ethyleneoxy unit, x = 0-5, typically 0-4, and most typically 0-2; y = 1-20, typically 1-12, more typically 2-8, and most typically 2-5; and z = 0-5, typically 0-4, more typically 0-2, and most typically 0. Thus, in addition to the 1-20 ethyleneoxy units, the C8-C18- alcohol alkoxylates may also include up to 5 propyleneoxy units. The number of propyleneoxy units, when present, may be as small as 0.1 mole PO per mole alcohol. The ethyleneoxy units and the propyleneoxy units may be added randomly or in blocks. The blocks may be added to the alcohol in any order. The alkoxylates may also include an alkyl group with 1-4 carbon atoms in the end position. Typically, the alkoxylates include 2-8 ethyleneoxy units and 0-2 propyleneoxy units. The alkyl group of the nonionic surfactants may 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 or6 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 Cl 1 alcohol + 4, 5, 6, 7 or 8 moles of EO, tridecyl alcohol + 4, 5, 6,7 or 8 moles of EO,. Another example is 2-butyloctanol + 5, 6 or 7 moles of EO. Wherever the degree of alkoxylation is discussed, the numbers represent molar average numbers.

[0042] The compositions may be acidic, neutral or alkaline. Alkaline compositions are typically based on alkali hydroxides, alkaline builders and / or complexing agents. The alkaline compositions are especially typical.

[0043] The alkali hydroxides typically are sodium or potassium hydroxide. The alkaline builders may be an alkali carbonate or an alkali hydrogen carbonate, such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate or potassium hydrogen carbonate, an alkali salt of a silicate, such as sodium silicate or sodium metasilicate, or alkali salts ofphosphates, such as sodium orthophosphate. Alkaline builders that act through complexation are, e.g., sodium pyrophosphate and sodium tripolyphosphate and the corresponding potassium salts. The builder / complexing agent may also be organic. Examples of organic builders / complexing agents are aminocarboxylates, such as Glutamic acid, N,N-diacetate (GLDA), Methylglycine, N,N-diacetate (MGDA), sodium nitrilotriacetate (Na3NTA), sodium ethylenediamine tetraacetate (EDTA), sodium diethylenetriamine pentaacetate, sodium 1,3-propylenediamine tetraacetate, and sodiumhydroxyethylethylenediamine triacetate; aminopolyphosphonates, such as nitrilotrimethylene phosphonate; organic phosphates; polycarboxylates, such as citrates; and alkali salts of gluconic acid, such as sodium or potassium gluconates.

[0044] In neutral and acidic compositions complexing and / or pH adjusting agents may also be added, such as citric acid, oxalic acid, acetic acid, sulfamic acid, hydrochloric acid.

[0045] In another typical embodiment, the cleaning composition comprises one or more chelates.

[0046] In one embodiment, the chelate is at least one aminocarboxylate chelate 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-hydroxyethyl-ethylenediaminetriacetic acid (HEDTA), diethylenetriaminepentaacetic acid (DTPA), ethylenediaminetetraproprionic acid triethylenetetraaminehexaacetic acid (TTHA), tetracetyl ethylene diamine (TAED), iminodisuccinic acid (IDS), ethanol diglycine (EDG), and the respective alkali metal, ammonium and substituted ammonium salts thereof. In a particularly typical embodiment, the aminocarboxylate chelate is selected from the group consisting of EDTA, GLDA, MGDA, salts thereof, and combinations thereof.

[0047] In another embodiment, the chelate is a non-aminocarboxylate chelate containing carboxylate functionality but not a nitrogen atom. In a typical embodiment, the non- aminocarboxylate chelate is a divalent or higher valency carboxylic acid. In an especially typical embodiment, the non-aminocarboxylate chelate is at least one member selected from the group consisting of citric acid, isocitric acid, 2,3 hydroxycitric acid, tricarballylic acid, ethanetricarboxylic acid (HET A), aconitic acid, succinic acid, maleic acid, fumaric acid, oxaloacetic acid, ketoglutaric acid, butanetetracarboxylic acid, polycarboxylic acid, and the respective alkali metal, ammonium and substituted ammonium salts thereof. In a particularlytypical embodiment, the non-aminocarboxylate chelate is selected from the group consisting of citric acid and salts thereof.

[0048] When one or more chelates are present in the formulation, they are present in a total combined chelate amount of greater than 0% by weight, typically at least 0.05% by weight, most typically at least 1% by weight, and at most 30% by weight, typically at most 20% by weight, more typically at most 15% by weight, and most typically at most 10% by weight.

[0049] In another typical embodiment, in addition to one or more nonionic surfactants and / or chelates, the cleaning composition further comprises one or more adjunct ingredients selected from the group consisting of aesthetic agents, anti-filming agents, antiredeposition agents, anti-spotting agents, anti-graying agents, beads, binders, biocides, bleach activators, bleach catalysts, bleach stabilizing systems, bleaching agents, brighteners, buffering agents, builders, carriers, clay, color speckles, control release agents, corrosion inhibitors, dish care agents, disinfectants, dispersant agents, draining promoting agents, drying agents, dyes, dye transfer inhibiting agents, enzymes, enzyme stabilizing systems, fillers, free radical inhibitors, fungicides, germicides, hydrotropes other than those of formula (I), opacifiers, perfumes, pH adjusting agents, pigments, processing aids, silicates, soil release agents, suds suppressors, anionic surfactants, cationic surfactants, stabilizers, thickeners, zeolite, and mixtures.

[0050] When one or more adjunct ingredients are present in the formulation, they are present in a total combined adjunct ingredient amount of greater than 0% by weight, typically at least 0.05% by weight, most typically at least 1% by weight, and at most 30% by weight, typically at most 20% by weight, more typically at most 15% by weight, and most typically at most 10% by weight.

[0051] The present disclosure contemplates both diluted and concentrated compositions.

[0052] Diluted compositions of the present disclosure are clear and stable. The clarity interval suitably is between 0-40°C, typically between 0-50°C, and most typically between 0- 60°C. This may be adapted by changing the ratio of hydrotrope to nonionic surfactant. The diluted compositions normally include at least 80% by weight of water, suitably at least 90% by weight, and normally at most 99.5% by weight of water, suitably at most 98% by weight.

[0053] Concentrated compositions of the present disclosure are clear and stable. The clarity interval suitably is between 0-40°C, typically between 0-50°C, and most typicallybetween 0-60°C. This may be adapted by changing the ratio of hydrotrope to nonionic surfactant. The concentrate normally includes at least 50% by weight of water, suitably at least 70% by weight, and normally at most 95% by weight of water, suitably at most 90% by weight.

[0054] There are several advantages connected with the use of the compounds of formula (I) as hydrotropes for nonionic surfactants. Firstly, they are excellent hydrotropes that also contribute to the cleaning performance of the compositions. Their cleaning efficiency is very good even at high dilutions of the compositions. Further, their biodegradability is expected to be better than that of previously known compounds, for example, BEROL® R648 NG (Nouryon) used in compositions for cleaning hard surfaces.

[0055] The disclosure will now be described in greater detail with reference to the following non-limiting examples.ExamplesExample 1A. Preparation of Alkyl Polyglycerylamine

[0056] The preparation of alkyl polyglycerylamines is known, for example, from U.S. Pre-Grant Publication No. 2022 / 0039378, the entire contents of which are hereby incorporated herein by reference.Raw-Materials Usable

[0057] Tallowamine Armeen TM-97 (AkzoNobel)

[0058] Oleylamine Armeen OM-97 (AkzoNobel)

[0059] Cocoalkylamine Armeen CD (AkzoNobel)

[0060] Glycidol (Acros)Abbreviations Used

[0061] “T” for “tallowamine”; “O” for "oleylamine”; “C” for “cocoamine”; “G” for“Glycerol units”; and “Q” for quatemized with methyl chloride.

[0062] For example:

[0063] T-5G (i.e., tallowamine 5G) means tallowamine with 5 glycerol units.

[0064] O-8G (i.e., oleylamine 8G) means oleylamine with 8 glycerol units.

[0065] C-20G (i.e., cocoamine 20G) means cocoamine with 20 glycerol units.Table 1Synthesis Procedure

[0066] For purposes of illustration only, the following procedure was used to create unquatemized sample #1 in Table 1 (a T-5G species outside the scope of the present claims), and similar procedures were used to synthesize the additional unquatemized samples, with the relevant fatty acid amine and glycidol molar ratios adjusted appropriately (as discussed below).

[0067] Glycidol (44.4 g, 0.6 mol) was added dropwise over a period of 3 hrs to tallowamine (32.04 g, 0.12 mol) stirred in a round bottom flask under nitrogen atmosphere keeping the temperature of the reaction mixture between 80° to 120° C. The reaction mixture was further stirred for about an hour at around 110° C. until IR analysis showed no more epoxide peaks around 840 cm"' due to glycidol. A clear pale brown viscous liquid product thus obtained was collected.

[0068] For Samples #2-#5, the process for Sample #1 was repeated using the indicated amine in the relevant molar ratio with glycidol. For example, for Sample #2, the process of Sample #1 was repeated using a molar ratio of 1:10 for tallowamine and glycidol, Sample #3 used a molar ratio of 1:8 for oleylamine and glycidol, and so forth.B. Quatemization

[0069] The unquatemized Samples 1-5 can be quaternized by charging a 2L Ti autoclave with approximately 1 meq / g of unquatemized sample and water, deoxygenating the contents by pressuring to 60 psig with N2 and depressurizing multiple times. Methyl chloride is added but with minimal excess to avoid hydrolysis. Quatemization is monitored by periodicallywithdrawing samples, measuring pH, and titrating for free amine. When free amine measures <5% of the starting amine, the reaction can be cooled and sparged with nitrogen. The contents can be collected without need of filtration and water removed using a rotary evaporator until the solution becomes viscous.Example 2

[0070] Analogous to Example 1, a product having 9 glycerol units can be prepared starting with C12-C14-alkyl(methyl)amine. Methods for preparing secondary amines are generally known; see, for example, US 9,000,218.Example 3

[0071] Analogous to Example 1, a product having 12 glycerol units can be prepared starting with C12-C14-alkyl(methyl)amine.Example 4

[0072] Analogous to Example 1, additional hydrotrobe products can be prepared as shown in the Table 2 from the indicated amines by introducing the indicated number of glycerol units:Table 2*Per glycerol chainExample 5

[0073] BEROL® R648 NG (Nouryon) is a market leading product for cleaning formulations that afford best-in-class cleaning, from a renewable, vegetable source with low or no environmental persistence and ecotoxicity. Though BEROL® R648 NG is readily biodegradable, it has certain drawbacks such as, it is an ethoxylate (not dioxane-free) and has low RCI (Renewable Carbon Index). With the fast changing regulations and environmental awareness, the availability of an EO-free (and dioxane free) product with higher RCI (typically >50%) that performs as well as BEROL® R648 NG is desired.

[0074] The hydrotropes of the present disclosure meet all the criteria mentioned above with performance as good as the benchmark BEROL® R648 NG. The hydrotropes of the present disclosure are dioxane-free and biobased because the glyercol units derive from glycidol, which is biobased. Moreover, some hydrotropes of the present disclosure may be readilybiodegradable with high RCI, and low / no toxicity. Also, they exhibit cleaning performance as good as the benchmark BEROL® R648 NG.

[0075] The hydrotropes of Examples 2 and 3 prepared in a different manner exhibit the ability to solubilize BEROL® 260 (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

[0076] The degreasing effect of the test formulations was then assessed on a white painted metal plate soiled uniformly with a tough-to-clean greasy soil collected from a train engine. The cleaning formulation (1:20 dilution in water) was applied simply by pouring it over the surface (non-mechanical cleaning). After a short time interval, the whole plate was rinsed with tap water and cleaning performance was assessed quantitatively. The results are tabulated below and depicted in FIG. 1. The cleaning performance of the hydrotropes of Examples 2 and 3 looks promising compared to the control.

[0077] While the present disclosure has been described in conjunction with the specific embodiments set forth above, many alternatives, modifications and other variations thereof will be apparent to those of ordinary skill in the art. All such alternatives, modifications and variations are intended to fall within the spirit and scope of the present disclosure.

Claims

CLAIMSWhat is claimed is:

1. A polyglycerol quaternary compound of the formula (I):R1mR - N- - (Gly)nX-(I)whereinR represents a C8-30 aliphatic group;R1independently represents a Cl-8 aliphatic group;Gly independently represents a polyglyceryl moiety having 7 to 20 glyceryl units; m represents 1 or 2; n represents 1 or 2; m + n = 3; andX- represents a counteranion.

2. The compound according to claim 1, wherein m represents 2, n represents 1, and the compound has the structure of formula (II): Gly X'(II) wherein the two R1groups are the same as or different from one another.

3. The compound according to claim 1, wherein m represents 1, n represents 2, and the compound has the structure of formula (III): Gly X'(ill) whereinthe two Gly groups are the same as or different from one another.

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

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

6. The compound according to claim 5, wherein R is a fatty linear or branched, saturated or unsaturated alkyl group having 12 or 14 carbon atoms.

7. The compound according to any one of the previous claims, wherein each R1is independently a Cl -4 aliphatic group.

8. The compound according to claim 7, wherein R1is methyl or ethyl.

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

10. The compound according to claim 9, wherein each Gly group is independently a polyglyceryl moiety having 7 to 12 glyceryl units.

11. The compound according to claim 10, wherein at least one Gly group is selected from glyceryl chains comprising a structure selected from the group consisting of:

12. The compound according to any one of the previous claims, wherein X" is a counterion selected from the group consisting of halides, salicylates, carbonates, and alkyl sulfates.

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

14. A process of preparing a polyglycerol quaternary compound of the formula (I) according to any one of claims 1-13, said process comprising:(a) reacting at least one primary or secondary amine with glycidol to yield a polyglyceryl amine; and(b) quatemizing the polyglycerol amine to yield a polyglycerol quaternary compound of the formula (I).

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

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

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