Multifunctional amphoteric hydrotropes, cleaning formulations containing them, and their use

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

[0002] This disclosure relates to multifunctional hydrotropes and their use in cleaning applications.

Background Art

[0003] As is well known in the art, many surfactants are too hydrophobic to dissolve in water. Attempting to introduce such surfactants into water can result in a cloudy or opaque solution. To solubilize such surfactants, it is typically necessary to add a hydrotrope, such as an amphoteric surfactant.

[0004] Known amphoteric surfactants 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 well as hydrotropes, especially when the alkyl group is less than C12. However, these alkylamine dipropionic acids have the disadvantage of being prepared using non-bio-based acrylic acid. As a result, products containing these amphoteric surfactants have a low renewable carbon index (RCI).

[0005] Other amphoteric surfactants used include amphoacetates made using monochloroacetic acid, preferably its sodium salt. These can be made using monoamines, diamines, triamines, and tetramines, and are commercially available from Nouryon under the trade name AMPHOLAK®. However, these amphoacetates yield undesirable NaCl as a byproduct. The presence of NaCl, an electrolyte, lowers the cloud point in the formulation, which is undesirable. Furthermore, these products derived from triamines and tetramines do not biodegrade readily.

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

[0007] Itaconic acid (methylenebutanediic acid, methylenesuccinic acid) is a crystalline, highly molten acid (melting point = 167-168°C) that is commercially produced by the fermentation of carbohydrates, and is therefore bio-based.

[0008] The reaction of itaconic acid with primary amines leads to lactam formation immediately after the desired product is formed by a favorable intramolecular dehydration reaction; therefore, itaconic acid cannot be simply substituted for acrylic acid in the process used to produce alkylamine dipropionic acid and its salts. The resulting lactam does not function well as a hydrotrope due to its insufficient hydrophilic properties.

[0009] The object of this disclosure is to develop bio-based, multifunctional hydrotropes for cleaning formulations that are environmentally sustainable and have low or no environmental toxicity. [Overview of the project]

[0010] This 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 linear or branched lower alkylene group having 1 to 8 carbon atoms bonded or optionally substituted with one or more COOX3 groups. X1, X2, and X3 independently represent negative charges or counterions.

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

[0012] In another embodiment, this disclosure relates to a process for preparing a compound according to any one of claims 1 to 6, wherein the process is: (a) A multicarboxylic acid of the following formula, [ka] During the ceremony, W represents a linear or branched lower alkyl group having 1 to 8 carbon atoms. m represents either 0 or 1. The process involves reacting the salt or ester thereof with a secondary amine of the following formula, [ka] (b) optionally includes a step of neutralizing with a base at least partially.

[0013] This disclosure, in another embodiment, (a) at least one compound of formula (I) as described herein, (b) It relates to an aqueous cleaning composition containing water and...

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

Brief Description of the Drawings

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

[0016] [Figure 1A] Figure 1A is a diagram showing the detergency of ARMEEN® 1M1214D itaconate (C12-14 alkylmethylamine itaconate) and control "A" (BEROL® R648 NG (quaternary C12-14 alkylmethylamine ethoxylate methyl chloride)) on a plate soiled with engine grease in the absence of NaOH. [Figure 1B] Figure 1B is a diagram showing the detergency of ARMEEN® 1M1214D itaconic acid and control "C" (BEROL® R648 NG) on another plate soiled with engine grease in the presence of 2% NaOH.

Embodiments for Carrying out the Invention

[0017] The compound of formula (I) can be derived from any polycarboxylic acid containing a carbon-carbon double bond.

[0018] In a preferred embodiment, the compound of formula (I) is derived from a polycarboxylic acid of the following formula.

Chemical Formula

[0019] In a particularly preferred embodiment, the polycarboxylic acid is selected from the group consisting of itaconic acid, methylidenemalonic acid, methylideneglutaric acid, maleic acid, fumaric acid, citraconic acid, and mesaconic acid.

[0020] The carboxylic acid functionality is any suitable cation, particularly Mg, in X1, X2, X3, etc. 2+ Ca 2+ NH4 + , K + Or Na + The mixture can be partially or completely neutralized using alkali (earth) metal ions such as 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, such as reactions 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 following 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 a particularly preferred embodiment, the secondary amine is selected from the group consisting of octylmethylamine, cocoalkylmethylamine, laurylmethylamine, n-decylmethylamine, fat alkylmethylamine, soybean alkylmethylamine, oleylalkylamine, and C12 / 14 alkylmethylamine.

[0023] In a more preferred embodiment, the compound of formula (I) has the following 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 counterion.

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

[0025] In an alternative embodiment, in the preceding equation, one of X1 and X2 represents H, and the other represents a negative charge or counterion, in particular sodium.

[0026] As described above, the compound of formula (I) is (a) Multicarboxylic acids of the following formula [ka] The process involves reacting the salt or ester thereof with a secondary amine of the following formula, [ka] (b) Prepared by a process that optionally includes a step of neutralizing with a base at least partially.

[0027] Two different addition modes are intended in the process. In the first embodiment, a secondary amine is added to a reaction mixture containing a multicarboxylic acid. In the second embodiment, a multicarboxylic acid is added to a reaction mixture containing a secondary amine.

[0028] Neutralization of multicarboxylic acids can be carried out either before (pre-neutralization) or after (post-neutralization) the reaction with the secondary amine. In one embodiment, the reaction is carried out in the absence of NaOH, yielding an acid product characterized by the presence of a COOH group. In another embodiment, the reaction is carried out using 1 equivalent of NaOH to produce a monosodium salt. In yet another embodiment, the reaction is carried out using 2 equivalents of NaOH to produce a disodium salt. This disclosure aims to cover any degree of partial neutralization, i.e., non-neutralization, any degree of partial neutralization, and complete neutralization. In the most preferred embodiment, the product is a monosodium salt.

[0029] In addition to the multicarboxylic acid and secondary amine, the reaction mixture may contain water alone, or a mixture of water and a suitable organic solvent, such as an alcohol like ethanol or methanol, or a glycol like ethylene glycol, monopropylene glycol (MPG), or glycerol, with MPG being the most preferred, followed by glycerol. The amount of solvent is preferably 0 to 80% by weight of the reaction mixture, most preferably 40 to 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, a catalyst is not required, but the use of an appropriate catalyst is also considered.

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

[0032] The reaction process can be monitored using IR and / or Raman spectroscopy, or HPLC. The purity and composition of the resulting product 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. Using a molar excess of up to 25%–50% of itaconic acid can reduce the amount of unreacted alkylamine. Even with a 25% molar excess of itaconic acid, the product will still contain some residual amine. However, the resulting product will exhibit good performance. Too much alkylamine in the product is undesirable because the unreacted amine remains insoluble in the formulation due to its hydrophobic nature. Since itaconic acid is water-soluble and water is a major component of the formulation, excess itaconic acid remaining in the product is not as significant a problem as having unreacted secondary amine.

[0034] The activity percentage 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, for example, household cleaning, industrial cleaning, all-purpose cleaning, car washing, acidic and caustic cleaning, deck and floor cleaning, hard surface cleaning, metal cleaning, food and beverage cleaning, automatic and manual dishwashing, laundry detergents, and more.

[0036] For these purposes, the cleaning formulation may contain, in addition to the compound of formula (I) disclosed and water, other conventional components well known in the art of cleaning.

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

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

[0039] Nonionic alkylene oxide adducts are well-known conventional products, and the molecules consist of a hydrophobic moiety and a moiety containing alkylene oxy units, the latter of which is hydrophilic. Thus, this disclosure relates to the use of a compound of formula (I) as a hydrotrope for a nonionic surfactant in aqueous solution. In other words, this disclosure relates to improving the solubilization of a nonionic surfactant for making a composition having good cleaning performance, wherein water, a nonionic surfactant, a compound having formula (I) as defined above, and other optional components are combined and / or mixed in one or more steps.

[0040] The amount of each component is preferably, a) at least 0.05% by weight, preferably at least 0.5% by weight, and up to 20% by weight, preferably up to 15% by weight, and most preferably up to 10% by weight of an alcohol alkoxylate, 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, most preferably up to 10% by weight, of the compound of formula (I), 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, an alkali hydroxide, alkali builder, and / or alkali complexing agent.

[0041] The composition is particularly preferably to contain alkali hydroxide, alkali builder, and / or alkali complexing agent.

[0042] The nonionic surfactant preferably has the following formula: [ka] In the formula, R3 is a C8-C18 linear or branched alkyl group, preferably C8-C12, PO is a propylene oxy unit, EO is an ethylene oxy 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, and z = 0-5, preferably 0-4, more preferably 0-2, most preferably 0. Thus, in addition to 1-20 ethylene oxy units, the C8-C18 alcohol alkoxylate may also contain up to 5 propylene oxy units. The number of propylene oxy units, if present, may be as small as about 0.1 moles of PO per mole of alcohol. The ethylene oxy units and propylene oxy units may be added randomly or in clusters. The clusters may be added to the alcohol in any order. The alkoxylate may also contain alkyl groups having 1-4 carbon atoms at the terminal positions. The alkoxylate preferably contains 2 to 8 ethylene oxy units and 0 to 2 propylene oxy units. The alkyl group of the nonionic surfactant 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 include 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, and 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.

[0043] The composition may be acidic, neutral, or alkaline. Alkaline compositions are typically based on alkali hydroxide, 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 bicarbonate such as sodium carbonate, potassium carbonate, sodium bicarbonate, or potassium bicarbonate, an alkali salt of a silicate such as sodium silicate or sodium metasilicate, or an alkali salt of phosphoric acid such as sodium orthophosphate. Alkali builders that act through complex formation include, for example, sodium pyrophosphate and sodium tripolyphosphate, and their corresponding potassium salts. The builder / complexing agent may also be organic. Examples of organic builders / complexing agents include 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 hydroxyethylethylenediaminetriacetate; aminopolyphosphonates such as nitrilotrimethylene phosphonate; polycarboxylates such as organic phosphates and citrates; and alkali salts of gluconic acid such as sodium or potassium gluconate.

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

[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 diacetic acid (MGDA), N,N-dicarboxymethyl glutamic acid (GLDA), N-hydroxyethyl iminodiacetic acid, nitrilotriacetic acid (NTA), ethylenediaminetetraacetic acid (EDTA), N-hydroxyethyl-ethylenediaminetriacetic acid (HEDTA), diethylenetriaminepentaacetic acid (DTPA), ethylenediaminetetrapropionic acid, triethylenetetraminehexaacetic acid (TTHA), tetraacetylethylenediamine (TAED), iminodisuccinic acid (IDS), ethanol diglycine (EDG), and alkali metals, ammonium and their substituted ammonium salts. In a particularly preferred embodiment, the aminocarboxylic acid chelate is selected from the group consisting of EDTA, GLDA, MGDA, their salts, and combinations thereof.

[0048] In another embodiment, the chelate is a non-aminocarboxylic acid chelate that contains carboxylic acid functionality but does not contain a nitrogen atom. In a preferred embodiment, the non-aminocarboxylic acid chelate is a carboxylic acid with a divalent or higher ionic value. In a particularly preferred embodiment, the non-aminocarboxylic acid chelate is at least one member selected from the group consisting of citric acid, isocitric acid, 2,3-hydroxycitric acid, tricarbaryl acid, ethanetricarboxylic acid (HETA), aconitic acid, succinic acid, maleic acid, fumaric acid, oxaloacetate, ketoglutaric acid, butanetetracarboxylic acid, polycarboxylic acid, and their respective alkali metals, ammonium, and substituted ammonium salts. In a particularly preferred embodiment, the non-aminocarboxylic 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 a total combined chelate amount of more 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, and most preferably up to 10% by weight.

[0050] In another preferred embodiment, in addition to one or more nonionic surfactants and / or chelates, the cleaning composition further comprises one or more additional components 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 stabilization systems, bleaches, gloss agents, buffers, builders, carriers, clays, color speckles, controlled release agents, rust inhibitors, dishwashing agents, disinfectants, dispersants, water drainage accelerators, drying agents, dyes, color transfer inhibitors, enzymes, enzyme stabilization systems, fillers, free radical inhibitors, antifungal agents, bactericides, hydrotropes other than formula (I), opacifiers, fragrances, pH adjusters, pigments, processing aids, silicates, antifouling agents, foam inhibitors, anionic surfactants, cationic surfactants, stabilizers, thickeners, zeolites, and mixtures.

[0051] If one or more adducts are present in the formulation, they are present in a total combined adduct amount of more 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, and most preferably up to 10% by weight.

[0052] This disclosure intends to provide both diluted and concentrated compositions.

[0053] The dilution compositions of this disclosure are clear and stable. The clarity range is preferably 0 to 40°C, more preferably 0 to 50°C, and most preferably 0 to 60°C. This can be adapted by changing the ratio of hydrotrope to nonionic surfactant. The dilution compositions typically contain at least 80% by weight of water, preferably at least 90% by weight, and typically up to 99.5% by weight of water, preferably up to 98% by weight.

[0054] The concentrated compositions of this disclosure are clear and stable. The clarity range is preferably 0 to 40°C, more preferably 0 to 50°C, and most preferably 0 to 60°C. This can be adapted by changing the ratio of hydrotrope to nonionic surfactant. The concentrated compositions typically contain at least 50% by weight of water, preferably at least 70% by weight, and typically up to 95% by weight of water, 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 BEROL® R648 NG (Nouryon), which is used in compositions for cleaning hard surfaces.

[0056] The present disclosure will be described in more detail here by reference to the following non-limiting embodiments. Examples

[0057] Example 1: ARMEEN® 1M1214D Monosodium Itaconate ARMEEN® 1M1214D monosodium itaconate can be prepared according to the following synthesis 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 an oil batch equipped with a magnetic stirrer, thermometer, N2 inlet (injection), and reflux condenser, and the mixture was stirred at room temperature (RT) while injecting N2. 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 reaction was complete, as indicated by the disappearance of the peak corresponding to C=C or the absence of further changes in the IR when monitored by infrared spectroscopy (IR).

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

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

[0062] Example 2: ARMEEN® 1M1214D Monosodium Itaconate Step 1: Add ARMEEN® 1M1214D and MPG to a 100 mL three-necked RB flask immersed in an oil batch equipped with a magnetic stirrer, thermometer, N2 inlet (injector), and reflux condenser, and stir at room temperature while injecting N2. Slowly add dimethyl itaconate to the reaction mixture while checking for exothermic reactions, setting the reaction mixture temperature to 50°C. Continue stirring until the reaction is complete, as assessed by the disappearance of the peak corresponding to C=C when monitored by infrared (IR) spectroscopy, or by the absence of further changes in the IR. (The reaction temperature may be increased in 10°C increments as needed until the reaction is complete.)

[0063] Step 2: Once the reaction is complete, water and aqueous NaOH solution are added, and the reaction mixture is stirred at approximately 70°C until hydrolysis is complete, while monitoring the disappearance of the ester carbonyl by IR. At this point, the product is transferred to a bottle.

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

[0065] Example 3: ARMEEN(registered trademark) 1M1214D monosodium fumarate Step 1: Fumaric acid and water were added to a 100 mL three-necked RB flask immersed in an oil batch equipped with a magnetic stirrer, thermometer, N2 inlet, and reflux condenser, and stirred at room temperature under N2 injection. NaOH was added to the stirred fumaric acid solution and stirred well (exothermic). When the reaction mixture became clear, MPG was added to the reaction mixture to set the reaction temperature 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 slowly added while maintaining the temperature below 80°C, bringing the reaction mixture temperature to 80°C. The progress of the reaction was monitored by IR until completion was indicated by the disappearance of the C=C and / or the 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 prepared from the following combinations of secondary amines and multicarboxylic acids. [Table 1]

[0069] Example 5 BEROL® R648 NG (Nouryon) is the market-leading cleaning formulation that provides best-in-class cleaning from renewable plant sources, ideally unlabeled at the point of sale, and has low or no environmental sustainability. While BEROL® R648 NG is readily biodegradable, it has certain drawbacks, including being an ethoxylate (not dioxane-free), a quaternary ammonium salt (quat), and having a low RCI (Renewable Carbon Index) of 29%. Due to rapidly changing regulations and environmental awareness, it is desirable to make available EO-free (and dioxane-free) non-quaternary ammonium salt (non-quat) products that perform similarly to BEROL® R648 NG but have a higher RCI (preferably over 50%).

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

[0071] The suitability of ARMEEN® 1M1214D itaconic acid for solubilizing BEROL® 260 (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 a white painted metal plate uniformly soiled with stubborn oil stains collected from a train engine. The cleaning formulations (diluted 1:40 in water) were applied simply by pouring them 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 summarized in the table below and illustrated in Figure 1A (cleaning formulations A and B without NaOH) and Figure 1B (cleaning formulations C and D containing 2% NaOH). [Table 2]

[0073] The data in the aforementioned table, as well as Figures 1A and 1B, demonstrate that the hydrotrope of the present invention (ARMEEN® 1M1214D itaconic acid) behaves similarly to the comparative hydrotrope (BEROL® R648 NG) in the absence or presence of NaOH in the washing formulation.

[0074] While this disclosure has been described in conjunction with the specific embodiments set forth above, many alternatives, modifications, and other variations thereto 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 this disclosure. The present invention includes the following embodiments. Section 1. 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 linear or branched lower alkylene group having 1 to 8 carbon atoms bonded or optionally substituted with one or more COOX3 groups. A compound in which X1, X2, and X3 independently represent a negative charge or counterion. Section 2. The compound described in item 1, which is derived from a multicarboxylic acid of the following formula, [ka] During the ceremony, W represents a linear or branched lower alkyl group having 1 to 8 carbon atoms. A compound, its salt, or ester, in which m represents either 0 or 1. Section 3. The compound according to item 2, wherein the multicarboxylic acid is selected from the group consisting of itaconic acid, methylidenemalonic acid, methylideneglutaric acid, maleic acid, fumaric acid, citraconic acid, and mesaconic acid. Section 4. A compound according to any one of items 1 to 3, derived from a secondary amine of the following formula, [ka] During the ceremony, R1 represents an aliphatic linear or branched saturated or unsaturated alkylene group having 8 to 14 carbon atoms. A compound in which R2 represents a linear or branched saturated or unsaturated lower alkylene group having 1 to 3 carbon atoms. Section 5. The compound according to claim 4, wherein the secondary amine is selected from the group consisting of octylmethylamine, cocoalkylmethylamine, laurylmethylamine, n-decylmethylamine, fat alkylmethylamine, soybean alkylmethylamine, and C12 / 14 alkylmethylamine. Section 6. A compound according to item 1 having the following formula, [ka] During the ceremony, R1 represents an aliphatic linear or branched saturated or unsaturated alkylene group having 12 or 14 carbon atoms. A compound in which X1 and X2 independently represent a negative charge or a counterion. Section 7. A process for preparing a compound described in any one of items 1 to 6, wherein the process is (a) A multicarboxylic acid of the following formula, [ka] During the ceremony, W represents a linear or branched lower alkyl group having 1 to 8 carbon atoms. A step of reacting a multicarboxylic acid, or a salt or ester thereof, in which m represents 0 or 1, with a secondary amine of the following formula, [ka] (b) A process comprising, optionally, a step of neutralizing with a base at least partially. Section 8. The process according to item 7, further comprising neutralizing at least partially with a base, wherein the base is sodium hydroxide. Section 9. (a) at least one compound described in any one of items 1 to 6, (b) an aqueous cleaning composition comprising water. Section 10. The aqueous cleaning composition according to item 9, further comprising one or more nonionic surfactants. Section 11. The aqueous cleaning composition according to claim 9 or 10, further comprising one or more chelates. Section 12. An aqueous cleaning composition according to any one of claims 9 to 11, further comprising one or more additional components 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 stabilization systems, bleaches, glossing agents, buffers, builders, carriers, clays, color speckles, controlled release agents, rust inhibitors, dishwashing agents, disinfectants, dispersants, water drainage accelerators, drying agents, dyes, color transfer inhibitors, enzymes, enzyme stabilization systems, fillers, free radical inhibitors, antifungal agents, bactericides, hydrotropes other than formula (I), opacifiers, fragrances, pH adjusters, pigments, processing aids, silicates, antifouling agents, foam inhibitors, anionic surfactants, cationic surfactants, stabilizers, thickeners, zeolites, and mixtures thereof. Section 13. A method for cleaning an object to be cleaned, comprising bringing the object into contact with an aqueous cleaning composition described in any one of items 9 to 12.

Claims

1. An amphoteric surfactant having the following formula, 【Chemistry 4】 During the ceremony, R １ However, it represents an aliphatic linear or branched saturated or unsaturated alkyl group having 12 to 14 carbon atoms. X １ and X ２ However, it is an amphoteric surfactant that independently represents a negative charge or counterion.

2. The amphoteric surfactant according to claim 1, derived from itaconic acid.

3. The amphoteric surfactant according to claim 1, derived from a secondary amine of the following formula, 【Transformation 3】 During the ceremony, R １ However, it represents an aliphatic linear or branched saturated or unsaturated alkyl group having 12 to 14 carbon atoms. R ２ However, CH ３ It is an amphoteric surfactant.

4. A process for preparing an amphoteric surfactant according to any one of claims 1 to 3, wherein the process comprises: (a) The step includes reacting itaconic acid with a secondary amine of the following formula, 【Transformation 6】 During the ceremony, R １ However, it represents an aliphatic linear or branched saturated or unsaturated alkyl group having 12 to 14 carbon atoms. R ２ is CH ３ is the process.

5. The process according to claim 4, further comprising a step of neutralizing with a base, wherein the base is sodium hydroxide.

6. (a) at least one amphoteric surfactant according to any one of claims 1 to 3, (b) an aqueous cleaning composition comprising water.

7. The aqueous cleaning composition according to claim 6, further comprising one or more nonionic surfactants.

8. The aqueous cleaning composition according to claim 6, further comprising one or more chelates.

9. The aqueous cleaning composition according to claim 6, further comprising one or more additional components 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 stabilization systems, bleaches, gloss agents, buffers, builders, carriers, clays, color speckles, controlled release agents, rust inhibitors, dishwashing agents, disinfectants, dispersants, water drainage accelerators, drying agents, dyes, color transfer inhibitors, enzymes, enzyme stabilization systems, fillers, free radical inhibitors, antifungal agents, bactericides, hydrotropes other than formula (I), opacifiers, fragrances, pH adjusters, pigments, processing aids, silicates, antifouling agents, foam inhibitors, anionic surfactants, cationic surfactants, stabilizers, thickeners, zeolites, and mixtures thereof.

10. A method for cleaning an object to be cleaned, comprising bringing the object into contact with the aqueous cleaning composition described in claim 6.

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