Multifunctional amphoteric hydrotropes, cleaning formulations containing them and their use - Patents.com

Abstract

The present disclosure relates to a compound of formula (I): [Formula 1] TIFF2025501153000020.tif39170, R1 represents an aliphatic linear or branched, saturated or unsaturated alkylene group having 8 to 30 carbon atoms; R2 represents a linear or branched, saturated or unsaturated lower alkylene group having 1 to 8 carbon atoms; n represents 0 or 1, Z and Y independently represent a bond or a straight or branched lower alkylene group having 1 to 8 carbon atoms optionally substituted with one or more groups COOX; X1, X2, and X3 independently represent a negative charge or a counter ion. The compounds of formula (I) act as hydrotropes and are useful in cleaning applications. Processes for preparing the compounds, cleaning compositions containing the compounds, and methods for cleaning objects using the compounds are also disclosed.

Description

[Technical field]

[0001] (Priority Claim) This application claims priority to U.S. Provisional Patent Application No. 63 / 294,113, filed December 28, 2021, the entire contents of which are incorporated herein by reference.

[0002] FIELD OF THE DISCLOSURE This disclosure relates to multi-functional hydrotropes and their use in cleaning applications. [Background technology]

[0003] As is well known in the art, many surfactants are too hydrophobic to be dissolved in water. When trying to introduce such surfactants into water, they may produce cloudy or opaque solutions. To solubilize such surfactants, they typically need to add hydrotropes, such as amphoteric surfactants.

[0004] Amphoteric surfactants known in the prior art include alkylamine dipropionic acids and their salts. Alkylamine dipropionic acid products are commercially available from Nouryon and other producers (under the trade name AMPHOLAK®). In these products, these amphoteric surfactants function as good hydrotropes, especially when the alkyl group is less than C12. However, these alkylamine dipropionic acids have the disadvantage of being prepared using acrylic acid, which is not biobased. As a result, products containing these amphoteric surfactants have a low renewable carbon index (RCI).

[0005] Other amphoteric surfactants that have been used include amphoacetates made using monochloroacetic acid, preferably its sodium salt. They can be made using monoamines, diamines, triamines, and tetramines, and are commercially available from Nouryon under the trade name AMPHOLAK®. However, these amphoacetates produce undesirable NaCl as a by-product. The presence of NaCl, an electrolyte, reduces the cloud point in the formulation, which is a disadvantage. Furthermore, these products derived from triamines and tetramines are not easily biodegradable.

[0006] Alkylamine dipropionic acids can be synthesized by reacting a primary fatty amine with acrylic acid via a Michael addition reaction. The product can be made / isolated in its acid form or as the monosodium or disodium sodium salt by adding NaOH.

[0007] Itaconic acid (methylenebutanedioic acid, methylenesuccinic acid) is a crystalline, high-melting acid (mp = 167-168 °C) produced commercially by fermentation of carbohydrates and is therefore biobased.

[0008] Itaconic acid cannot simply be substituted for acrylic acid in processes used to make alkylamine dipropionic acids and their salts, because the reaction of itaconic acid with primary amines results in lactam formation as soon as the desired product is formed by a favorable intramolecular dehydration reaction, and the resulting lactam does not work well as a hydrotrope due to insufficient hydrophilic properties.

[0009] It is an objective of the present disclosure to develop bio-based, multi-functional hydrotropes with low or no environmental persistence and toxicity for cleaning formulations. Summary of the Invention

[0010] The present disclosure relates in one embodiment to a compound of formula (I): [ka] During the ceremony, R1 represents an aliphatic linear or branched, saturated or unsaturated alkylene group having 8 to 30 carbon atoms; R2 represents a linear or branched, saturated or unsaturated lower alkylene group having 1 to 8 carbon atoms; n represents 0 or 1, Z and Y independently represent a bond or a straight or branched lower alkylene group having 1 to 8 carbon atoms optionally substituted with one or more groups COOX3; X1, X2, and X3 independently represent a negative charge or a counter ion.

[0011] Compounds in which one or more of X1, X2, and X3 represent H are also contemplated, and in particular compounds in which one of X1 and X2 represents H and the other represents a negative charge or counter ion.

[0012] The present disclosure relates in another embodiment to a process for preparing a compound according to any one of claims 1 to 6, said process comprising: (a) a multicarboxylic acid of the formula: [ka] During the ceremony, W represents a straight or branched lower alkyl group having 1 to 8 carbon atoms; m represents 0 or 1, or a salt or ester thereof with a secondary amine of the formula: [ka] (b) optionally, at least partially neutralizing with a base.

[0013] The present disclosure provides, in another embodiment, (a) at least one compound of formula (I) as described herein; (b) water.

[0014] The present disclosure, in yet another embodiment, relates to a method of cleaning an object to be cleaned, the method comprising contacting the object with an aqueous cleaning composition described herein. [Brief description of the drawings]

[0015] The present disclosure will now be described in more detail with reference to the drawings.

[0016] [Figure 1A] FIG. 1A shows the detergency of ARMEEN® 1M1214D itaconate (C12-14 alkylmethylamine itaconate) and control “A” (BEROL® R648 NG (quaternary C12-14 alkylmethylamine ethoxylate methyl chloride)) in the absence of NaOH on a plate soiled with engine grease. [Figure 1B] FIG. 1B illustrates the detergency of ARMEEN® 1M1214D itaconic acid and control “C” (BEROL® R648 NG) in the presence of 2% NaOH on another plate soiled with engine grease. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0017] The compounds of formula (I) may be derived from any multi-carboxylic acid that contains a carbon-carbon double bond.

[0018] In a preferred embodiment, the compound of formula (I) is derived from a multi-carboxylic acid of the following formula: [ka]

[0019] In particularly preferred embodiments, the multicarboxylic acid is selected from the group consisting of itaconic acid, methylidene malonic acid, methylidene glutaric acid, maleic acid, fumaric acid, citraconic acid, and mesaconic acid.

[0020] The carboxylic acid functionality can be substituted at X1, X2, X3, etc. with any suitable cation, particularly Mg 2+ , Ca 2+ , NH4 + , K + Or Na + The neutralization can be carried out partially or completely with alkaline (earth) metal ions such as, particularly sodium and potassium, most preferably sodium, or alkanolamines such as methanolamine, monoethanolamine (MEA), diethanolamine (DEA) triethanolamine (TEA), 2-amino-2-methyl-1-propanol (AMP), tris(hydroxymethyl)aminomethane (TRIS), or 2-(isopropylamino)ethanol (IPAE). Neutralization can be carried out using neutralization methods well known in the art, for example, reaction with sodium hydroxide or other suitable neutralizing agents.

[0021] In a preferred embodiment, the compound of formula (I) is also derived from a secondary amine of the formula: [ka] During the ceremony, R1 represents an aliphatic linear or branched, saturated or unsaturated alkylene group having 8 to 14 carbon atoms; R2 represents a linear or branched, saturated or unsaturated lower alkylene group having 1 to 3 carbon atoms.

[0022] In particularly preferred embodiments, the secondary amine is selected from the group consisting of octylmethylamine, cocoalkylmethylamine, laurylmethylamine, n-decylmethylamine, tallowalkylmethylamine, soybeanalkylmethylamine, oleylalkylamine, and C12 / 14 alkylmethylamine.

[0023] In a more preferred embodiment, the compound of formula (I) has the formula: [ka] During the ceremony, R1 represents an aliphatic linear or branched, saturated or unsaturated alkylene group having 12 or 14 carbon atoms; X1 and X2 independently represent a negative charge or a counter ion.

[0024] In a most preferred embodiment, in the formula immediately above, at least one of X1 or X2 is a sodium cation.

[0025] In an alternative embodiment, in the formula immediately above, one of X1 and X2 represents H, and the other represents a negative charge or counterion, particularly sodium.

[0026] As mentioned above, the compound of formula (I) (a) a multicarboxylic acid of the formula: [ka] or a salt or ester thereof with a secondary amine of the formula: [ka] (b) optionally, at least partially neutralizing with a base.

[0027] The process contemplates two different addition modes: in a first embodiment, the secondary amine is added to the reaction mixture containing the multi-carboxylic acid; in a second embodiment, the multi-carboxylic acid is added to the reaction mixture containing the secondary amine.

[0028] Neutralization of the multicarboxylic acid can be carried out either before (pre-neutralization) or after (post-neutralization) reaction with the secondary amine. In one embodiment, the reaction is carried out in the absence of NaOH, resulting in an acid product characterized by the presence of a COOH group. In another embodiment, the reaction is carried out using one equivalent of NaOH, resulting in the monosodium salt. In yet another embodiment, the reaction is carried out using two equivalents of NaOH, resulting in the disodium salt. The present disclosure aims to cover any degree of partial neutralization, i.e., from no neutralization, to any degree of partial neutralization, to complete neutralization. In the most preferred embodiment, the product is the monosodium salt.

[0029] Besides the multicarboxylic acid and the secondary amine, the reaction mixture will contain water alone or a mixture of water and a suitable organic solvent, for example an alcohol such as ethanol or methanol, or a glycol such as ethylene glycol, monopropylene glycol (MPG) or glycerol, with MPG being most preferred, followed by glycerol. The amount of solvent is preferably 0-80% by weight of the reaction mixture, most preferably 40-60% by weight. In one preferred embodiment, the solvent is removed from the product. In another preferred embodiment, the solvent is not removed and is therefore present in the product.

[0030] Typically, no catalyst is required, although the use of a suitable catalyst is contemplated.

[0031] The temperature can range from 25 to 110°C, or even higher, depending on the reactants. In the case of the reaction of itaconic acid and ARMEEN® 1M1214D, reactions carried out at temperatures above 110°C result in by-products, and therefore the temperature should be kept low. On the other hand, temperatures below 70°C result in long reaction times and incomplete reactions. The reaction with itaconic acid and ARMEEN® 1M1214D is preferably carried out at 70 to 85°C for up to 10 hours.

[0032] The reaction process can be monitored using IR and / or Raman spectroscopy, or HPLC. The purity and composition of the resulting products can be analyzed using H1 and C13 NMR, or LC-MS.

[0033] In some cases, the resulting product may be a mixture of the expected product and both unreacted starting materials. A molar excess of up to 25%-50% of itaconic acid can be used to reduce the amount of unreacted alkylamine. Even with a 25% molar excess of itaconic acid, the product still contains some residual amine. However, the resulting product gives good performance. Having too much alkylamine content in the product is a disadvantage because the unreacted amine remains insoluble in the formulation since itaconic acid is hydrophobic and water is the major component of the formulation. Having excess itaconic acid remaining in the product is not as big a problem as having unreacted secondary amine.

[0034] The % activity of the product is preferably 20-100%, most preferably 40-60%.

[0035] Cleaning formulations containing the disclosed compounds are useful for a variety of cleaning purposes and can be formulated for example, household cleaning, industrial cleaning, all purpose cleaning, car washing, acid and caustic cleaning, deck and floor cleaning, hard surface cleaning, metal cleaning, food and beverage cleaning, automatic and manual dishwashing, laundry detergents, and the like.

[0036] For such purposes, the cleaning formulations may contain, in addition to the disclosed compounds of formula (I) and water, other conventional ingredients well known in the cleaning art.

[0037] In a preferred embodiment, the cleaning composition comprises one or more non-ionic surfactants.

[0038] In a more preferred embodiment, the one or more nonionic surfactants are selected from the group consisting of nonionic alkylene oxide adducts, especially C8-C18 linear and branched alcohols (alcohol alkoxylates) and amine alkoxylates containing 1-20 ethyleneoxy units and 0-5 propyleneoxy units. Nonionic alkyl polyglyceryl ethers made with C8-C18 linear and branched alcohols and 1-10 glycidol units, or alkyl polyglycerylamines made with C8-C18 linear and branched alkyl amines and 1-10 glycidol units, can also be used.

[0039] Nonionic alkylene oxide adducts are well-known conventional products, whose molecules contain a hydrophobic part and a part containing an alkyleneoxy unit, said latter part having hydrophilic characteristics.Accordingly, the present disclosure relates to the use of the compound of formula (I) as a hydrotrope for nonionic surfactants in aqueous solutions.In other words, the present disclosure relates to the improvement of the solubilization of nonionic surfactants to make compositions with good cleaning performance, where water, nonionic surfactants, compounds having formula (I) as defined above, and other optional ingredients are combined and / or mixed in one or several steps.

[0040] The amounts of the components are preferably: a) at least 0.05% by weight, preferably at least 0.5% by weight, and at most 20% by weight, preferably at most 15% by weight, and most preferably at most 10% by weight of alcohol alkoxylates, b) at least 0.02% by weight, preferably at least 0.1% by weight, and up to 20% by weight, preferably up to 15% by weight, and most preferably up to 10% by weight, of a compound of formula (I), and c) 0% by weight, preferably at least 0.05% by weight, and up to 30% by weight, preferably up to 20% by weight, more preferably up to 15% by weight, and most preferably up to 10% by weight of alkali hydroxide, alkali builder, and / or alkali complexing agent.

[0041] It is particularly preferred that the composition contains an alkali hydroxide, an alkali builder, and / or an alkali complexing agent.

[0042] The non-ionic surfactant preferably has the formula: [ka] In the formula, R3 is a C8-C18 linear or branched alkyl group, preferably C8-C12, PO is a propyleneoxy unit, EO is an ethyleneoxy unit, x=0-5, preferably 0-4, most preferably 0-2, y=1-20, preferably 1-12, more preferably 2-8, most preferably 2-5, z=0-5, preferably 0-4, more preferably 0-2, most preferably 0. Thus, in addition to 1-20 ethyleneoxy units, the C8-C18 alcohol alkoxylate may also contain up to 5 propyleneoxy units. The number of propyleneoxy units, if present, may be as small as 0.1 mole PO per mole alcohol. The ethyleneoxy and propyleneoxy units may be added randomly or in several chunks. The chunks may be added to the alcohol in any order. The alkoxylate may also contain an alkyl group having 1-4 carbon atoms in the terminal position. The alkoxylates preferably contain 2 to 8 ethyleneoxy units and 0 to 2 propyleneoxy units. The alkyl groups of the nonionic surfactants may be linear or branched, saturated or unsaturated. Suitable linear nonionic surfactants are C9-C11 alcohols + 4, 5, 6, 7, or 8 moles of EO, C8-C10 alcohols + 3, 4, 5, 6, 7, or 8 moles of EO, C12-C14 alcohols + 3, 4, 5, 6, 7, or 8 moles of EO, and C10-C14 alcohols + 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, tridecyl alcohol + 4, 5, 6, 7, or 8 moles of EO. Another example is 2-butyloctanol + 5, 6, or 7 moles of EO. When discussing the degree of alkoxylation, the numbers represent the molar average number.

[0043] The compositions may be acidic, neutral, or alkaline. Alkaline compositions are typically based on alkali hydroxides, alkali builders, and / or complexing agents. Alkaline compositions are particularly preferred.

[0044] The alkali hydroxide is preferably sodium hydroxide or potassium hydroxide. The alkali builder 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 an alkali salt of a phosphoric acid such as sodium orthophosphate. Alkaline builders that act through complexation are, for example, 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 ethylenediaminetetraacetate (EDTA), sodium diethylenetriaminepentaacetate, sodium 1,3-propylenediaminetetraacetate, and sodium hydroxyethylethylenediaminetriacetate, aminopolyphosphonates such as nitrilotrimethylene phosphonate, organic phosphates, polycarboxylates such as citrate, and alkali salts of gluconic acid such as sodium or potassium gluconate.

[0045] In neutral and acidic compositions, complexing agents and / or pH adjusters may also be added, such as citric acid, oxalic acid, acetic acid, sulfamic acid, hydrochloric acid, and the like.

[0046] In another preferred embodiment, the cleaning composition comprises one or more chelates.

[0047] In one embodiment, the chelate is at least one aminocarboxylic acid chelate selected from the group consisting of methylglycine diacetate (MGDA), N,N-dicarboxymethylglutamic acid (GLDA), N-hydroxyethyliminodiacetate, nitrilotriacetate (NTA), ethylenediaminetetraacetate (EDTA), N-hydroxyethyl-ethylenediaminetriacetate (HEDTA), diethylenetriaminepentaacetate (DTPA), ethylenediaminetetraproprionic acid, triethylenetetraminehexaacetate (TTHA), tetraacetylethylenediamine (TAED), iminodisuccinic acid (IDS), ethanoldiglycine (EDG), and the respective alkali metal, ammonium, and substituted ammonium salts thereof. In a particularly preferred embodiment, the aminocarboxylic acid chelate is selected from the group consisting of EDTA, GLDA, MGDA, salts thereof, and combinations thereof.

[0048] In another embodiment, the chelate is a non-amino carboxylic acid chelate that contains a carboxylic acid functionality but no nitrogen atoms. In a preferred embodiment, the non-amino carboxylic acid chelate is a carboxylic acid of divalent or higher valency. In a particularly preferred embodiment, the non-amino carboxylic acid chelate is at least one member selected from the group consisting of citric acid, isocitric acid, 2,3 hydroxycitric acid, tricarballylic acid, ethanetricarboxylic acid (HETA), aconitic acid, succinic acid, maleic acid, fumaric acid, oxaloacetic acid, ketoglutaric acid, butanetetracarboxylic acid, polycarboxylic acids, and their respective alkali metal, ammonium, and substituted ammonium salts thereof. In a particularly preferred embodiment, the non-amino carboxylic acid chelate is selected from the group consisting of citric acid and its salts.

[0049] If one or more chelates are present in the formulation, they are present in an amount of the total combined chelates greater than 0% by weight, preferably at least 0.05% by weight, most preferably at least 1% by weight, and up to 30% by weight, preferably up to 20% by weight, more preferably up to 15% by weight, most preferably up to 10% by weight.

[0050] In another preferred embodiment, in addition to the one or more nonionic surfactants and / or chelates, the cleaning composition further comprises one or more additional ingredients selected from the group consisting of aesthetic agents, anti-filming agents, anti-redeposition agents, anti-spotting agents, anti-graying agents, beads, binders, biocides, bleach activators, bleach catalysts, bleach stabilizing systems, bleaching agents, brighteners, buffers, builders, carriers, clays, color speckles, controlled release agents, rust inhibitors, dish care agents, disinfectants, dispersants, drainage aids, drying agents, dyes, dye transfer inhibitors, enzymes, enzyme stabilizing systems, fillers, free radical inhibitors, mold inhibitors, germicides, hydrotropes other than those of formula (I), opacifiers, fragrances, pH adjusters, pigments, processing aids, silicates, soil inhibitors, suds suppressors, anionic surfactants, cationic surfactants, stabilizers, thickeners, zeolites, and mixtures.

[0051] When one or more additional ingredients are present in the formulation, they are present in a total combined additional ingredient amount of greater than 0% by weight, preferably at least 0.05% by weight, most preferably at least 1% by weight, and up to 30% by weight, preferably up to 20% by weight, more preferably up to 15% by weight, most preferably up to 10% by weight.

[0052] The present disclosure contemplates both diluted and concentrated compositions.

[0053] The dilute compositions of the present disclosure are transparent and stable. The transparency interval is preferably 0-40°C, more preferably 0-50°C, and most preferably 0-60°C. This can be adapted by changing the ratio of hydrotrope and non-ionic surfactant. The dilute compositions usually contain at least 80% by weight of water, preferably at least 90% by weight, and usually up to 99.5% by weight of water, preferably up to 98% by weight.

[0054] The concentrated compositions of the present disclosure are clear and stable. The transparency interval is preferably 0-40°C, more preferably 0-50°C, and most preferably 0-60°C. This can be adapted by varying the ratio of hydrotrope and non-ionic surfactant. The concentrated compositions usually contain at least 50% water by weight, preferably at least 70% by weight, and usually up to 95% water by weight, more preferably up to 90% by weight.

[0055] There are several advantages associated with the use of compounds of formula (I) as hydrotropes for nonionic surfactants. Firstly, they are excellent hydrotropes that also contribute to the cleaning performance of the composition. Their cleaning efficiency is very good even at high dilutions of the composition. Furthermore, their biodegradability is expected to be better than that of previously known compounds, such as, for example, BEROL® R648 NG (Nouryon), used in compositions for cleaning hard surfaces.

[0056] The present disclosure will now be described in more detail with reference to the following non-limiting examples. Working Example

[0057] Example 1: ARMEEN® 1M1214D Monosodium Itaconate ARMEEN® 1M1214D monosodium itaconate can be prepared according to the following synthetic scheme. [ka]

[0058] More specifically, ARMEEN® 1M1214D monosodium itaconate can be prepared as follows.

[0059] Step 1: ARMEEN® 1M1214D (C12-14 alkylmethylamine / Nouryon) and monopropylene glycol (MPG) were added to a 100 mL three-necked RB flask immersed in oil batch equipped with a magnetic stirrer, thermometer, N2 inlet (inlet), and reflux condenser and stirred at room temperature (RT) with N2 injection. Solid itaconic acid was added to the stirred reaction mixture and the reaction mixture temperature was set to 80° C. Stirring was continued until the completion of the reaction, as assessed by disappearance of the peak corresponding to C═C or no further change in IR as monitored by infrared spectroscopy (IR).

[0060] Step 2: Once the reaction is complete, add water to the reaction mixture, then slowly add 50% NaOH solution via disposable pipette while keeping the reaction mixture temperature below 80° C. Stir the reaction mixture well after addition and transfer the product to a bottle.

[0061] The resulting product is 50% active in 50:50 MPG+H2O.

[0062] Example 2: ARMEEN® 1M1214D Monosodium Itaconate Step 1: ARMEEN® 1M1214D and MPG were added to a 100 mL three-necked RB flask immersed in oil batch equipped with a magnetic stirrer, thermometer, N2 inlet (injection), and reflux condenser, and stirred at room temperature while injecting N2. Dimethyl itaconate was added slowly to the reaction mixture while checking for exotherm, and the reaction mixture temperature was set to 50°C. Stirring was continued until the completion of the reaction, as assessed by disappearance of the peak corresponding to C=C or no further change in IR, as monitored by infrared spectrum (IR). (The reaction temperature can be increased in 10°C increments as necessary until the reaction is complete.)

[0063] Step 2: Once the reaction is shown to be complete, water and aqueous NaOH are added and the reaction mixture is stirred at approximately 70° C. while being monitored by IR for the disappearance of the ester carbonyl until hydrolysis shows completion, at which point the product is transferred to a bottle.

[0064] The resulting product is 50% active in MPG+H2O+MeOH.

[0065] Example 3: ARMEEN® 1M1214D Monosodium Fumarate Step 1: Fumaric acid and water were added to a 100 mL 3-neck RB flask immersed in oil batch equipped with a magnetic stirrer, thermometer, N2 inlet, and reflux condenser and stirred at room temperature under N2 inlet. NaOH was added to the stirring fumaric acid solution and stirred well (exothermic). Once the reaction mixture became clear, MPG was added to the reaction mixture and the reaction temperature was set to 75°C and an IR was taken when the reaction mixture became clear again.

[0066] Step 2: Once the reaction mixture temperature stabilized at approximately 75° C., the amine was added slowly while maintaining the temperature below 80° C., and the reaction mixture temperature was set to 80° C. The reaction progress was monitored by IR until completion was indicated by disappearance of C═C and / or stabilization of other peaks. Once the reaction was complete, the product was transferred to a bottle.

[0067] The resulting product is 50% active in MPG+water.

[0068] Example 4 In a similar manner, amphoteric surfactants can be made from the following combinations of secondary amines and multicarboxylic acids: [Table 1]

[0069] Example 5 BEROL® R648 NG (Nouryon) is a market leading product for cleaning formulations that provides best-in-class cleaning with low or no environmental persistence, ideally non-labeled at point of sale, and derived from renewable plant sources. BEROL® R648 NG is readily biodegradable but has certain drawbacks, such as being an ethoxylate (not dioxane-free), a quaternary ammonium salt (quat), and having a low RCI (renewable carbon index) of 29%. With rapidly changing regulations and environmental awareness, it is desirable to have available an EO-free (and dioxane-free), non-quat product with a higher RCI (preferably above 50%) that performs similarly to BEROL® R648 NG.

[0070] ARMEEN® 1M1214D Itaconic Acid meets all of the above criteria with comparable performance to the benchmark BEROL® R648 NG. ARMEEN® 1M1214D Itaconic Acid has a high RCI (approximately 95%), low / non-toxicity, and cleaning performance similar to the benchmark BEROL® R648 NG, and is expected to be readily biodegradable.

[0071] The suitability of ARMEEN® 1M1214D itaconic acid to solubilize BEROL® 260 (a C9-C11 alcohol ethoxylate) and the cleaning power of the resulting formulations were tested in comparison to BEROL® R648 NG. Test formulations A and B contained 5% BEROL® 260, 8% DISSOLVINE® GL-47-S, and either 4% BEROL® R648 NG or 2.4% ARMEEN® 1M1214D itaconic acid, respectively. Test formulations C and D contained 5% BEROL® 260, 8% DISSOLVINE® GL-47-S, 2% NaOH, and either 4% BEROL® R648 NG or 2.4% ARMEEN® 1M1214D itaconic acid, respectively.

[0072] The degreasing effect of the test formulations was evaluated on white painted metal plates uniformly soiled with stubborn oily soils collected from train engines. The cleaning formulations (diluted 1:40 in water) were applied by simply pouring onto the surface (non-mechanical cleaning). After a short time interval, the entire plate was rinsed with tap water and the cleaning performance was quantitatively evaluated. The results are tabulated below and illustrated in Figure 1A (respective cleaning formulations A and B without NaOH) and Figure 1B (respective cleaning formulations C and D with 2% NaOH). [Table 2]

[0073] The data in the preceding tables and Figures 1A and 1B show that the hydrotrope of the present invention (ARMEEN® 1M1214D itaconic acid) performs similarly to the comparative hydrotrope (BEROL® R648 NG) in the absence or presence of NaOH in cleaning formulations.

[0074] 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, and all such alternatives, modifications, and variations are intended to fall within the spirit and scope of the present disclosure.

Claims

1. A compound of formula (I) 【Chemistry 1】 During the ceremony, R １ represents an aliphatic linear or branched, saturated or unsaturated alkylene group having 8 to 30 carbon atoms; R ２ represents a linear or branched, saturated or unsaturated lower alkylene group having 1 to 8 carbon atoms; n represents 0 or 1; Z and Y are independently a bond or one or more groups COOX ３ represents a straight-chain or branched lower alkylene group having 1 to 8 carbon atoms optionally substituted with X １ , X ２ , and X ３ represents, independently, a negative charge or counterion.

2. 2. A compound according to claim 1 which is derived from a multicarboxylic acid of the formula: 【Chemistry 2】 During the ceremony, W represents a straight or branched lower alkyl group having 1 to 8 carbon atoms; a compound in which m represents 0 or 1, or a salt or ester thereof.

3. 3. The compound of claim 2, wherein the multicarboxylic acid is selected from the group consisting of itaconic acid, methylidene malonic acid, methylidene glutaric acid, maleic acid, fumaric acid, citraconic acid, and mesaconic acid.

4. A compound according to any one of claims 1 to 3, derived from a secondary amine of the formula 【Chemistry 3】 During the ceremony, R １ represents an aliphatic linear or branched, saturated or unsaturated alkylene group having 8 to 14 carbon atoms; R ２ represents a linear or branched, saturated or unsaturated lower alkylene group having 1 to 3 carbon atoms.

5. 5. The compound of claim 4, wherein the secondary amine is selected from the group consisting of octylmethylamine, cocoalkylmethylamine, laurylmethylamine, n-decylmethylamine, tallow alkylmethylamine, soybean alkylmethylamine, and C12 / 14 alkylmethylamine.

6. 2. The compound of claim 1 having the formula: 【Chemistry 4】 During the ceremony, R １ represents an aliphatic linear or branched, saturated or unsaturated alkylene group having 12 or 14 carbon atoms; X １ and X ２ represents, independently, a negative charge or counterion.

7. A process for preparing a compound according to any one of claims 1 to 6, said process comprising: (a) a multicarboxylic acid of the formula: 【Chemistry 5】 During the ceremony, W represents a straight or branched lower alkyl group having 1 to 8 carbon atoms; m represents 0 or 1; or a salt or ester thereof with a secondary amine of the formula: 【Chemistry 6】 (b) optionally, at least partially neutralizing with a base.

8. 8. The process of claim 7, further comprising at least partially neutralizing with a base, said base being sodium hydroxide.

9. (a) at least one compound according to any one of claims 1 to 6; (b) water.

10. 10. The aqueous cleaning composition of claim 9, further comprising one or more non-ionic surfactants.

11. 11. The aqueous cleaning composition of claim 9 or claim 10, further comprising one or more chelates.

12. 12. The aqueous cleaning composition of any one of claims 9 to 11, further comprising one or more additional ingredients selected from the group consisting of aesthetic agents, anti-filming agents, anti-redeposition agents, anti-spotting agents, anti-graying agents, beads, binders, biocides, bleach activators, bleach catalysts, bleach stabilizing systems, bleaching agents, brighteners, buffers, builders, carriers, clays, color speckles, controlled release agents, rust inhibitors, dish care agents, sanitizing agents, dispersants, drainage aids, drying agents, dyes, dye transfer inhibitors, enzymes, enzyme stabilizing systems, fillers, free radical inhibitors, mildew inhibitors, bactericides, hydrotropes other than those of formula (I), opacifiers, fragrances, pH adjusters, pigments, processing aids, silicates, soil release agents, suds suppressors, anionic surfactants, cationic surfactants, stabilizers, thickeners, zeolites, and mixtures thereof.

13. A method for cleaning an object to be cleaned, comprising contacting said object with an aqueous cleaning composition according to any one of claims 9 to 12.

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