Surfactants and methods for producing the same

Abstract

To provide a novel surfactant that exhibits excellent surface activity and is industrially useful. [Solution] The surfactant is composed of a compound represented by the following general formula (1). [Formula 1] TIFF2026082238000010.tif39141 However, in the above general formula (1), R is a C6-50 alkyl group, a C6-50 alkenyl group, a C6-50 alkylphenyl group, a residue of polyoxyalkylene (C2-4, degree of polymerization 1-100) alkyl (C6-30) ether, a residue of polyoxyalkylene (C2-4, degree of polymerization 1-100) alkenyl (C6-30) ether, or a residue of polyoxyalkylene (C2-4, degree of polymerization 1-100) alkylphenyl (C6-30) ether. Also, A is an alkali metal, an alkanolamine, or an amine.

Description

Technical Field

[0001] This application relates to a surfactant and a method for producing the same, and particularly relates to a surfactant having excellent surfactant properties and excellent safety.

Background Art

[0002] Surfactants exhibit excellent foaming power, detergency, emulsifying power, dispersing power, etc. at the interface between water and air or at the interface between water and oil, etc., and have been widely used as detergents, dispersants, foaming agents, defoaming agents, emulsifying agents, etc. conventionally. Further, surfactants are roughly classified into ionic surfactants that ionize into ions when dissolved in water and non-ionic surfactants that do not become ions, and further, ionic surfactants are classified into anionic surfactants, cationic surfactants, and amphoteric surfactants according to the type of ions generated.

[0003] Among such surfactants, anionic surfactants are the cheapest in terms of cost and exhibit excellent foaming power, detergency, emulsifying power, dispersing power, etc., and are widely used in various household products and industrial products. As the anionic group in anionic surfactants, four types, namely, a sulfone group, a sulfate ester group, a carboxyl group, and an acidic phosphate ester group, are common.

[0004] However, anionic surfactants having any of the four types of anionic groups mentioned above are known to have several problems, as described below. Specifically, while the most representative anionic surfactant having a sulfone group, sodium linear alkylbenzene sulfonate (LAS), has excellent cleaning power, it is highly irritating to the skin, so users must wear gloves when using dish soap containing it. Furthermore, anionic surfactants having a sulfone group or anionic surfactants containing a sulfate ester group generally require special treatment equipment in the manufacturing facility because toxic anhydrous sulfuric acid gas is commonly used during their production. Moreover, it has been pointed out that anionic surfactants having a carboxyl group, such as soap, do not exhibit their cleaning power and other effects unless the pH is 10 or higher, that they can cause skin irritation, and that they do not exhibit their cleaning power and other effects in hard water. Furthermore, anionic surfactants having an acidic phosphate ester group are generally synthesized (manufactured) using alcohol and anhydrous phosphoric acid, but conventionally known common synthesis methods have the problem that not only monoesters with surfactant properties but also diesters without surfactant properties are synthesized in large quantities.

[0005] Under these circumstances, various attempts have been made to solve the various problems associated with anionic surfactants. For example, Patent Document 1 (Japanese Patent Publication No. 2007-326819) discloses a method for producing a phosphate monoester that has a low phosphate diester content, high phosphate monoester purity, and low orthophosphoric acid and unreacted organic hydroxy compound content. [Prior art documents] [Patent Documents]

[0006] [Patent Document 1] Japanese Patent Publication No. 2007-326819 [Overview of the project] [Problems that the invention aims to solve]

[0007] Under these circumstances, the present inventors conducted various studies on surfactants having novel structures and discovered that acidic phosphonic acid esters can be produced by efficiently condensing phosphonic acid or low molecular weight phosphonic acid monoesters with a predetermined alcohol or other hydroxy compound. Furthermore, they found that alkali metal salts and amine salts of such acidic phosphonic acid esters exhibit excellent surfactant properties, leading to the completion of the present invention. In other words, the present invention was made against this background, and its objective is to provide a novel surfactant that exhibits excellent surfactant properties and is industrially useful. The present invention also aims to provide an advantageous method for producing such surfactants that exhibit excellent surfactant properties. [Means for solving the problem]

[0008] Furthermore, the present invention can be suitably implemented in various embodiments listed below to solve the aforementioned problems, and any combination of these embodiments is also possible. It should be understood that the embodiments or technical features of the present invention are not limited to those described below, but can be understood based on the description of the entire specification.

[0009] (1) A surfactant comprising a compound represented by the following general formula (1). [ka] However, in the above general formula (1), R is an alkyl group of C6-50, C6-50 Lukenyl group, C6-50 alkylphenyl group, polyoxyalkylene (C2-4, (Degree of polymerization 1-100) Alkyl (C6-30) ether residues, polyoxyalkylene (C2-4, degree of polymerization 1-100) alkenyl (C6-30) ether residues, or Rioxyalkylene (C2-4, degree of polymerization 1-100) alkylphenyl (C6-30 ) is an ether residue. Also, A is an alkali metal, alkanolamine, or amine. It is of the same type. (2) A method for producing a surfactant according to embodiment (1), characterized in that it comprises a step of dehydrating a C6-50 alkyl alcohol with phosphonic acid, a step of dehydrating a C6-50 alkenyl alcohol with phosphonic acid, or a step of dehydrating a C6-50 phenylalkyl alcohol with phosphonic acid. (3) A method for producing a surfactant according to embodiment (2), comprising the step of neutralizing the reaction product obtained through the dehydration step with sodium alcoholate (C1-5) or potassium alcoholate (C1-5) in alcohol (C1-5), and then filtering the reaction product. (4) A method for producing a surfactant according to embodiment (3), comprising a step of washing the filtered reaction product. (5) A method for producing a surfactant according to embodiment (1), characterized by comprising a transesterification step of dialkyl (C1-5) hydrogen phosphite with polyoxyalkylene (C2-4, degree of polymerization 1-100) alkyl (C6-30) ether, polyoxyalkylene (C2-4, degree of polymerization 1-100) alkenyl (C6-30) ether, or polyoxyalkylene (C2-4, degree of polymerization 1-100) alkylphenyl (C6-30) ether. (6) A method for producing a surfactant according to embodiment (5), comprising the step of neutralizing the reaction product obtained through the dehydration step with sodium alcoholate (C1-5) or potassium alcoholate (C1-5) in alcohol (C1-5), and then filtering the reaction product. (7) A method for producing a surfactant according to embodiment (6), comprising a step of washing the reaction product after filtration. [Effects of the Invention]

[0010] Thus, the surfactant according to the present invention is composed of an alkali metal salt of an acidic phosphonic acid ester, and due to the characteristic structure of such an alkali metal salt of an acidic phosphonic acid ester, it possesses both excellent surface activity and excellent safety. Furthermore, such surfactants exhibiting excellent properties can be advantageously manufactured by the surfactant manufacturing method according to the present invention. [Modes for carrying out the invention]

[0011] Incidentally, the surfactant according to the present invention consists of a compound represented by the following general formula (1). [ka] In the general formula (1) above, R is a C6-50 alkyl group, a C6-50 alkenyl group, a C6-50 alkylphenyl group, a residue of polyoxyalkylene (C2-4, degree of polymerization 1-100) alkyl(C6-30) ether, a residue of polyoxyalkylene (C2-4, degree of polymerization 1-100) alkenyl(C6-30) ether, or a residue of polyoxyalkylene (C2-4, degree of polymerization 1-100) alkylphenyl(C6-30). Also, A is an alkali metal, an alkanolamine, or an amine.

[0012] The compound represented by the above general formula (1) can be produced, for example, by producing (synthesizing) a phosphonic acid monoester according to the following production methods I and II, and then neutralizing the phosphonic acid monoester.

[0013] -Manufacturing method I- In this manufacturing method, phosphonic acid monoesters are produced (synthesized) by dehydrating alkyl alcohols having 6 to 50 carbon atoms (C6-50 alkyl alcohols), C6-50 alkenyl alcohols, or C6-50 phenylalkyl alcohols (hereinafter collectively referred to as alcohols) with phosphonic acid (H3PO3).

[0014] In the manufacturing method I, the alcohol to be subjected to the dehydration reaction with phosphonic acid is an alkyl alcohol having 6 to 50 carbon atoms, an alkenyl alcohol having 6 to 50 carbon atoms, or a phenylalkyl alcohol having 6 to 50 carbon atoms. Preferably, an alkyl alcohol having 10 to 30 carbon atoms (C10-30 alkyl alcohol), an alkenyl alcohol having 10 to 30 carbon atoms, or a phenylalkyl alcohol having 10 to 30 carbon atoms is used. In the manufacturing method I, either natural alcohol or synthetic alcohol can be used. For example, natural alcohols such as lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, arachidyl alcohol, behenyl alcohol, palmitoleyl alcohol, oleyl alcohol, etc., and synthetic alcohols such as linear alcohols using α-olefin as a raw material, oxo alcohols, Ziegler alcohols, and gerb alcohol can be used.

[0015] Phosphonic acid (H3PO3) is a solid at room temperature and may not easily dissolve in the above-mentioned alcohols. Therefore, usually, phosphonic acid is dissolved in a predetermined solvent to prepare a solution, and this solution is mixed with the above-mentioned alcohols, and then the solvent is removed, whereby the dehydration reaction can proceed uniformly. Examples of the solvent that can be used include methanol, ethanol, n-propanol, isopropanol, butanol, etc. However, when using a highly hydrophilic one among the above-mentioned alcohols (C6-50 alkyl alcohol, etc.), it is also possible to mix phosphonic acid and the above-mentioned alcohols without using a solvent for dissolving phosphonic acid and cause the dehydration reaction to proceed.

[0016] The mixing ratio (molar ratio) of phosphonic acid and the above-mentioned alcohols (alkyl alcohols with C6 - 50 carbon atoms, others) is preferably [phosphonic acid]:[alcohols] = 5:1 to 0.5:1, more preferably [phosphonic acid]:[alcohols] = 3:1 to 0.6:1. When the amount of alcohols is excessive, the production amount of phosphonic acid diester that does not exhibit surface activity increases, which is not preferable. Within the above range, different from the reaction between alcohol and phosphoric anhydride, phosphonic acid monoester is preferentially produced, and the production amount of phosphonic acid diester can be suppressed low.

[0017] The dehydration of alcohols by phosphonic acid can be carried out by heating a mixture of phosphonic acid (and a predetermined solvent) and alcohols. The heating method is not particularly limited, and any known heating method such as electrothermal heating, heating by steam or high frequency can be adopted. In order to facilitate the progress of the dehydration reaction, it is preferable to heat under a reduced pressure of 300 torr or less, and more preferably under a reduced pressure of 100 torr or less. Also, the heating temperature is preferably 100 - 250°C, more preferably 110 - 180°C. In addition to the method of heating under reduced pressure, it is also possible to carry out the dehydration reaction by azeotroping a mixture of phosphonic acid (and a predetermined solvent) and alcohols with toluene, xylene, etc. The heating temperature for carrying out the dehydration reaction by such azeotroping is preferably 100 - 200°C, more preferably 110 - 180°C. In the various dehydration methods described above, it is also possible to use sulfuric acid, p-toluenesulfonic acid, Lewis acid catalysts, etc. to promote the dehydration reaction.

[0018] - Manufacturing Method II - In this manufacturing method, a dialkyl(C1-10) hydrogen phosphite is used as a starting material and hydrolyzed to produce (synthesize) a monoalkyl(C1-10) hydrogen phosphite. The obtained monoalkyl(C1-10) hydrogen phosphite is then transesterified with a polyoxyalkylene (C2-4, degree of polymerization 1-100) alkyl(C6-30) ether, a polyoxyalkylene (C2-4, degree of polymerization 1-100) alkenyl(C6-30) ether, or a polyoxyalkylene (C2-4, degree of polymerization 1-100) alkylphenyl(C6-30) ether to produce (synthesize) a phosphonic acid monoester.

[0019] Here, the dialkylhydrogen phosphite used as one of the raw materials is preferably one with 1 to 10 carbon atoms, and more preferably one with 1 to 5 carbon atoms. Dialkylhydrogen phosphites with more than 10 carbon atoms exhibit high hydrophobicity, which makes hydrolysis difficult, and even if hydrolysis proceeds, it may be difficult to remove the resulting alcohol.

[0020] As for the specific manufacturing method, first, a dialkyl(C1~10) hydrogen phosphite is hydrolyzed with equimolar water at an environment of 0~100°C to obtain a monoalkyl(C1~10) hydrogen phosphite. Then, a polyoxyalkylene(C2~4, degree of polymerization 1~100) alkyl(C6~30) ether, a polyoxyalkylene(C2~4, degree of polymerization 1~100) alkenyl(C6~30) ether, or a polyoxyalkylene(C2~4, degree of polymerization 1~100) alkylphenyl(C6~30) ether is added to the obtained monoalkyl(C1~10) hydrogen phosphite, and a transesterification reaction is carried out to obtain the desired phosphonic acid monoester.

[0021] In this process, both hydrolysis and transesterification are preferably carried out under reduced pressure of 300 torr or less, and more preferably under reduced pressure of 100 torr or less, in order to facilitate the reaction. Furthermore, both hydrolysis and transesterification are advantageously carried out under heating, with a heating temperature of 100 to 250°C, and more preferably 110 to 180°C. In addition to heating under reduced pressure, it is also possible to carry out the hydrolysis and transesterification reactions by azeotropic reaction with toluene, xylene, etc. The heating temperature when carrying out hydrolysis reactions by azeotropic reaction is preferably 100 to 200°C, and more preferably 110 to 180°C.

[0022] The phosphonic acid monoesters obtained according to the above-described manufacturing methods I and II can be subjected to the neutralization treatment described later without purification to produce surfactants consisting of compounds according to the present invention. However, if the obtained phosphonic acid monoesters contain phosphonic acid as an impurity, and there is a risk that such phosphonic acid may inhibit the surfactant activity of the target compound, then preferably the phosphonic acid monoesters obtained according to the above-described manufacturing methods I and II are purified. Examples of such purification methods include adding a solvent such as hexane, toluene, or ethyl ether to the product in an equivalent to three times the amount of the product, followed by washing with water, or washing with a hydrophilic solvent such as ethylene glycol, propylene glycol, or glycerin, and then purifying.

[0023] Then, by neutralizing the phosphonic acid monoester with sodium alkoxide (C1-C5), potassium alkoxide (C1-C5), alkali metal salts, alkanolamines, amines, etc., a compound exhibiting the excellent surfactant properties desired by the present invention can be obtained. Note that the compounds used to neutralize the phosphonic acid monoester are not limited to those mentioned above.

[0024] Examples of alkali metal salts include lithium salts, sodium salts, potassium salts, rubidium salts, and cesium salts. These can be used individually, and it is also possible to use two or more of them in combination.

[0025] Furthermore, while alkanolamines are formed by the addition of an alkylene oxide to a nitrogen compound having active hydrogen, in the present invention, alkanolamines formed by the addition of an alkylene oxide having 2 to 5 carbon atoms to a nitrogen compound having active hydrogen are advantageously used when neutralizing phosphonic acid monoesters. Examples of such alkanolamines include monoethanolamine, diethanolamine, triethanolamine, monoisopropanolamine, diisopropanolamine, triisopropanolamine, tetraisopropanolethylenediamine, monoethanolmorpholine, monoethanolcyclohexylamine, and diethanolcyclohexylamine. These can be used individually, or two or more can be used in combination.

[0026] Furthermore, in the present invention, the amines used when neutralizing the phosphonic acid monoester are preferably amine compounds having an alkyl group, alkenyl group, aralkyl group, or alkylphenyl group with 2 to 50 carbon atoms. More preferably, the alkyl group has 4 to 24 carbon atoms. Examples of amine compounds having such predetermined carbon-containing groups include primary amines such as butylamine, hexylamine, octylamine, laurylamine, myristylamine, cetylamine, stearylamine, alatinylamine, behenylamine, palmitooleylamine, oleylamine, coconutamine, and beef tallowamine; dibutylamine, dihexylamine, dioctylamine, dilaurylamine, dimyristylamine, dicetylamine, distearylamine, dialatinylamine, dibehenylamine, dipalmitoleylamine, dioleylamine, and diya Examples include secondary amines such as cyamines and ditafamines; tertiary amines such as dimethylbutylamine, dimethylhexylamine, dimethyloctylamine, dimethyllaurylamine, dimethylmyristylamine, dimethylcetylamine, dimethylstearylamine, dimethylalatinylamine, dimethylbehenylamine, dimethylpalmitoleylamine, dimethyloleylamine, dimethylcoconutamine, and dimethyltafamine; and polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine, and tetraethylenepentamine.

[0027] When neutralizing phosphonic acid monoesters using alkali metal salts or the like as described above, it is possible to select and adopt an appropriate method from among various conventionally known methods.

[0028] The compound obtained by the above method, represented by the following general formula (1), exhibits excellent surfactant properties such as foaming ability, penetrating ability, and surface tension reduction ability, and is therefore advantageously applicable to household detergents, toiletries, laundry detergents, industrial detergents, reactive surfactants, textile oils, spill treatment agents, defoamers, and the like. [ka] In the general formula (1) above, R is a C6-50 alkyl group, a C6-50 alkenyl group, a C6-50 alkylphenyl group, a residue of polyoxyalkylene (C2-4, degree of polymerization 1-100) alkyl(C6-30) ether, a residue of polyoxyalkylene (C2-4, degree of polymerization 1-100) alkenyl(C6-30) ether, or a residue of polyoxyalkylene (C2-4, degree of polymerization 1-100) alkylphenyl(C6-30). Also, A is an alkali metal, an alkanolamine, or an amine. [Examples]

[0029] The present invention will be further clarified by showing some embodiments below, but it goes without saying that the present invention is not limited in any way by the description of such embodiments. Furthermore, it should be understood that, in addition to the embodiments below and the specific descriptions above, various changes, modifications, and improvements can be made to the present invention based on the knowledge of those skilled in the art, as long as they do not depart from the spirit of the present invention.

[0030] -Example 1- In a 200 mL four-necked flask, 20 g of isopropyl alcohol and 22.5 g (0.27 mol) of phosphonic acid (reagent grade, purity: 98%) were added, and the flask was heated to 50°C to dissolve the phosphonic acid in the isopropyl alcohol. Next, 71.9 g (0.27 mol) of oleyl alcohol (product name: Angecol 90N, manufactured by Shin Nippon Rika Co., Ltd., OHV: 209.4) was added to the flask, and the reaction was carried out at 100-130°C under reduced pressure of 50 torr for 20 hours. After that, the reaction solution in the flask was diluted with 200 g of ethanol, and then neutralized to pH 7.5 by adding a 20% sodium ethoxide ethanol solution. The reaction solution after neutralization was filtered, and the filtrate was air-dried on an aluminum tray. The mixture of the resulting air-dried product and 200 g of acetone was filtered, and subsequently the mixture of the residue (filter) and 200 g of acetone was filtered again. By drying the resulting residue (filter material), 80.7 g of solid product was obtained.

[0031] The obtained product had a phosphorus content of 8.3% and a purity of 95%. NMR analysis of the product confirmed that it was oleyl acid phosphite sodium.

[0032] -Example 2- 60 g of isopropyl alcohol and 83.5 g (1.0 mol) of phosphonic acid (reagent grade, purity: 98%) were added to a 500 ml four-necked flask. The flask was heated to 50°C to dissolve the phosphonic acid in the isopropyl alcohol. Next, 188.1 g (1.0 mol) of lauryl alcohol (product name: Conol 20P, manufactured by Shin Nippon Rika Co., Ltd., OHV: 298.5) was added to the flask, and the reaction was carried out at 100-130°C under reduced pressure of 50 torr for 20 hours. After that, the reaction solution in the flask was diluted with 200 g of ethanol, and then neutralized to pH 7.5 by adding a 20% sodium ethoxide ethanol solution. The reaction solution after neutralization was filtered, and the filtrate was air-dried on an aluminum tray. The mixture of the resulting air-dried product and 200 g of acetone was filtered, and then the mixture of the residue (filter) and 200 g of acetone was filtered again. By drying the resulting residue (filter), 210.5 g of solid product was obtained.

[0033] The obtained product had a phosphorus content of 10.0% and a purity of 94%. NMR analysis of the product confirmed that it was sodium lauryl acid phosphate.

[0034] -Example 3- In a 200 mL four-necked flask, 10 g of isopropyl alcohol and 22.5 g (0.27 mol) of phosphonic acid (reagent grade, purity: 98%) were added. The flask was heated to 50°C to dissolve the phosphonic acid in the isopropyl alcohol. Next, 88.8 g (0.3 mol) of polyoxyethylene EO3 laurate (product name: Blaunon EL-1502P, manufactured by Aoki Oil & Fat Industry Co., Ltd., molecular weight: 296) was added to the flask, and the reaction was carried out at 100-130°C under reduced pressure of 50 torr for 20 hours. After that, the reaction solution in the flask was diluted with 200 g of n-hexane and washed four times with 300 g of 20% saline solution. The reaction solution after washing was dehydrated under reduced pressure and filtered to obtain 100.3 g of polyoxyethylene lauryl ether EO3 acid phosphite. The phosphorus content was 7.4%, and the purity was 86%.

[0035] -Example 4- In a 200 mL four-necked flask, 10 g of isopropyl alcohol and 22.5 g (0.27 mol) of phosphonic acid (reagent grade, purity: 98%) were added. The flask was heated to 50°C to dissolve the phosphonic acid in the isopropyl alcohol. Next, 132.3 g (0.3 mol) of polyoxyethylene EO4 oleate (product name: Licanon UA-5004, manufactured by Shin Nippon Rika Co., Ltd., molecular weight: 441) was added to the flask, and the reaction was carried out at 100-130°C under reduced pressure of 50 torr for 20 hours. After that, the reaction solution in the flask was diluted with 200 g of n-hexane and washed four times with 300 g of 20% saline solution. The reaction solution after washing was dehydrated under reduced pressure and filtered to obtain 141.1 g of polyoxyethylene oleyl ether EO4 acid phosphite. The phosphorus content was 5.2%, and the purity was 85%.

[0036] -Example 5- 49.4 g (0.405 mol) of diethyl hydrogen phosphite (manufactured by Toho Chemical Industry Co., Ltd.) and deionized water were added to a 200 mL four-necked flask and mixed at 50°C for 5 hours. The acid value of the mixture changed from 4 to 451. 107.9 g (0.405 mol) of oleyl alcohol (product name: Angecol 90N, manufactured by Shin Nippon Rika Co., Ltd., OHV: 209.4) was added to the mixture, and the reaction was carried out at 100-130°C under reduced pressure of 50 torr for 20 hours. Subsequently, the reaction solution in the flask was diluted with 200 g of ethanol, and then neutralized to pH 7.5 by adding a 20% sodium ethoxide ethanol solution. The neutralized reaction solution was filtered, and the filtrate was air-dried on an aluminum tray. The mixture of the air-dried material obtained and 200 g of acetone was filtered, and the mixture of the residue (filtered material) and 200 g of acetone was filtered again. By drying the resulting residue (filtered material), 113.7 g of oleyl acid phosphite sodium was obtained. The phosphorus content was 8.0%, and the purity was 91%.

[0037] The surfactant activity of each compound obtained as described above was measured and evaluated according to the methods shown below. For comparison, the following compounds were prepared and used. Comparison example A: Sodium lauryl sulfate (Product name: Alscope LS30, manufactured by Toho Chemical Industry Co., Ltd.) Comparative Example B: Sodium polyoxyethylene lauryl ether EO3 sulfate (Product name: Sandet EN, manufactured by Sanyo Chemical Industries, Ltd.) Comparative Example C: Polyoxyethylene lauryl ether EO3 phosphate (Product name: Phosphanol ML-220, manufactured by Toho Chemical Industry Co., Ltd.) Comparative Example D: Oleyl acid phosphate (acidic phosphate ester) (Product name: JP-518, manufactured by Johoku Chemical Industry Co., Ltd.)

[0038] Here, Comparative Example A (sodium lauryl sulfate) was used for comparison with the compound related to Example 2 (sodium lauryl acid phosphite), and the difference between the two is that Comparative Example A is a sulfate ester and Example 2 is a phosphonic acid ester. Furthermore, Comparative Examples B (sodium polyoxyethylene lauryl ether EO3 sulfate) and C (polyoxyethylene lauryl ether EO3 phosphate) were used for comparison with the compound related to Example 3 (polyoxyethylene lauryl ether EO3 acid phosphite), and the difference between them is that Comparative Example B is a sulfate ester, Comparative Example C is a phosphate ester, and Example 3 is a phosphonic acid ester. In addition, Comparative Example D (oleyl acid phosphite) was used for comparison with the compound related to Example 1 (sodium oleyl acid phosphite) and Example 5 (sodium oleyl acid phosphite), and the difference between them is that Comparative Example D is a phosphate ester and Example 1 and Example 5 are phosphonic acid esters.

[0039] Furthermore, the compounds in Example 3, Example 4, Comparative Example C, and Comparative Example D were neutralized with sodium hydroxide to prepare 20% aqueous solutions, which were then subjected to the following tests.

[0040] -surface tension- For each compound in Examples 1 to 3 and Comparative Examples A to D, the surface tension (10) was measured using a Dunouy surface tension meter in accordance with JIS-K-3362:2008 "Test Methods for Household Synthetic Detergents" "8.4 Surface Tension 8.4.2 Ring Method". -3 The N / m value was measured. The measurement results are shown in Table 1 below. [Table 1]

[0041] As is clear from the results in Table 1, the compound according to the present invention exhibits a surface tension that is equal to or lower than that of conventional products.

[0042] -Foaming power- Each compound from Examples 1 to 3 and Comparative Examples A to D was added to ultrapure water in a proportion of 0.25% based on its solid content. After standing overnight, a drop test was performed at 25°C according to the method specified in "ISO 696:1975," and the foam height (mm) was measured 5 minutes after dropping. The measurement results are shown in Table 2 below. [Table 2]

[0043] As is clear from the results in Table 2, the compounds according to the present invention were found to have foaming power equivalent to or better than that of conventional products. For example, in Example 3, the foaming power was equivalent to that of Comparative Example C and significantly better than that of Comparative Example B.

[0044] -Penetration power- Each compound from Examples 1 to 3 and Comparative Examples A to D was added to ultrapure water in a proportion of 0.25% based on its solid content. After standing overnight, the felt sedimentation time (seconds) was measured at 25°C according to the canvas disk method specified in "ISO 8022:1990". The measurement results are shown in Table 3 below.

[0045] [Table 3]

[0046] As is clear from the results in Table 2, the compounds according to the present invention were found to have penetration power equivalent to or better than that of conventional products. For example, in Example 3, the penetration power was equivalent to that of Comparative Example C and significantly better than that of Comparative Example B.

[0047] -Cleaning power- The cleaning power was evaluated using the Leenuts improved testing machine in accordance with "9.2 Method for Evaluating the Cleaning Power of Kitchen Synthetic Detergents" in JIS-K-3362:2008 "Test Methods for Household Synthetic Detergents". Specifically, an artificial smudge was prepared by mixing 10g of beef tallow and 10g of soybean oil, dissolving it with 1.0g of oil red in 60mL of chloroform. Six microscope slides were immersed in this artificial smudge, then removed, dried, and weighed. The amount of smudge adhering to the slides (amount of smudge before washing) was calculated from this measurement. Using the Leenuts improved testing machine, a 0.1% solution of the formulation shown in Table 4 below was tested at 30°C. After the test, the slides were dried and weighed. The amount of smudge remaining on the slides (amount of smudge after washing) was calculated from this measurement. The cleaning power (%) was then calculated using the following formula (a). The calculation results are shown in Table 5 below.

[0048] [Table 4]

[0049] [Table 5]

[0050] As is clear from the results in Table 5, it can be recognized that the compounds according to the present invention exhibit cleaning power equivalent to or better than that of conventional products.

Claims

1. A surfactant comprising a compound represented by the following general formula (1). 【Chemistry 1】 However, in the above general formula (1), R is a C6-50 alkyl group, a C6-50 alkenyl group, a C6-50 alkylphenyl group, a residue of polyoxyalkylene (C2-4, degree of polymerization 1-100) alkyl (C6-30) ether, a residue of polyoxyalkylene (C2-4, degree of polymerization 1-100) alkenyl (C6-30) ether, or a residue of polyoxyalkylene (C2-4, degree of polymerization 1-100) alkylphenyl (C6-30) ether. Also, A is an alkali metal, an alkanolamine, or an amine.

2. The method for producing a surfactant according to claim 1, A method for producing a surfactant, characterized by comprising a step of dehydrating a C6-50 alkyl alcohol with phosphonic acid, a step of dehydrating a C6-50 alkenyl alcohol with phosphonic acid, or a step of dehydrating a C6-50 phenylalkyl alcohol with phosphonic acid.

3. A method for producing a surfactant according to claim 2, comprising the step of neutralizing the reaction product obtained through the dehydration step with sodium alcoholate (C1-5) or potassium alcoholate (C1-5) in alcohol (C1-5), and then filtering the reaction product.

4. A method for producing a surfactant according to claim 3, comprising the step of washing the reaction product after filtration.

5. The method for producing a surfactant according to claim 1, A method for producing a surfactant, characterized by comprising a transesterification step of dialkyl (C1-5) hydrogen phosphite with polyoxyalkylene (C2-4, degree of polymerization 1-100) alkyl (C6-30) ether, polyoxyalkylene (C2-4, degree of polymerization 1-100) alkenyl (C6-30) ether, or polyoxyalkylene (C2-4, degree of polymerization 1-100) alkylphenyl (C6-30) ether.

6. A method for producing a surfactant according to claim 5, comprising the step of neutralizing the reaction product obtained through the dehydration step with sodium alcoholate (C1-5) or potassium alcoholate (C1-5) in alcohol (C1-5), and then filtering the reaction product.

7. A method for producing a surfactant according to claim 6, comprising the step of washing the reaction product after filtration.

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