SULFONATE COMPOSITION

Abstract

In addition to an organic solvent (B), an inorganic metal compound (C), and water as component (D), a sulfonate composition disclosed in the present invention contains a compound (A) represented by ROOC—(CH.sub.2).sub.p—CH(SO.sub.3M)—CH.sub.2—(CH.sub.2).sub.q—COOR′, where M represents a cation, R and R′ independently represent a group selected from an alkyl group with 10 carbons and an alkenyl group with 10 carbons, p and q each represent a number of 0 to 18, and a total of p and q is 0 to 18. The mass ratios of components (A), (B), (C), and (D) to the total content of the components (A)-(D) are as follows: 0.05≤A/(A+B+C+D)≤0.71, B/(A+B+C+D)≥0.05, C/(A+B+C+D)>0, and 0.10<D/(A+B+C+D)<0.60.

Claims

1. A sulfonate composition, comprising: a compound represented by the following formula (1) as component (A):
ROOC—(CH.sub.2).sub.p—CH(SO.sub.3M)—CH.sub.2—(CH.sub.2).sub.q—COOR′  (1) wherein M represents a cation, R and R′ represent 2-propylheptyl group, p and q each represent a number of 0 or more and 18 or less, and a total of p and q is 0 or more and 18 or less; an organic solvent as component (B); an inorganic metal compound as component (C); and water as component (D), wherein A/(A+B+C+D), which is a mass ratio of the component (A) to a total content of the components (A), (B), (C) and (D), is 0.05 or more and 0.71 or less, B/(A+B+C+D), which is a mass ratio of the component (B) to the total content of the components (A), (B), (C) and (D), is 0.05 or more, C/(A+B+C+D), which is a mass ratio of the component (C) to the total content of the components (A), (B), (C) and (D), is more than 0, and D/(A+B+C+D), which is a mass ratio of the component (D) to the total content of the components (A), (B), (C) and (D) is more than 0.10 and less than 0.60.

2. (canceled)

3. The sulfonate composition according to claim 1, wherein the component (B) is at least one selected from the group consisting of a monohydric alcohol and a polyhydric alcohol.

4. The sulfonate composition according to claim 1, wherein the component (C) is at least one selected from the group consisting of an alkali metal sulfate, an alkali metal carbonate, an alkali metal hydrogen carbonate, an alkali metal hydroxide, and an alkaline earth metal hydroxide.

5. The sulfonate composition according to claim 1, wherein the component (B) is a monohydric alcohol, and the composition satisfies the following condition (Ia) or the following condition (Ib): condition (Ia): A/(A+B+C+D) is 0.05 or more and 0.71 or less, B/(A+B+C+D) is more than 0.05, C/(A+B+C+D) is more than 0 and less than 0.001, and D/(A+B+C+D) is more than 0.10 and 0.50 or less; condition (Ib): A/(A+B+C+D) is 0.05 or more and 0.71 or less, B/(A+B+C+D) is 0.05 or more, C/(A+B+C+D) is 0.001 or more, and D/(A+B+C+D) is 0.15 or more and less than 0.60.

6. The sulfonate composition according to claim 5, wherein the composition satisfies the condition (Ia), which further includes a condition that a mass ratio of a total content of the components (A) and (B) to the total content of the components (A), (B), (C) and (D) is more than 0.10 and less than 0.90.

7. The sulfonate composition according to claim 5, wherein the composition satisfies the condition (Ib) which further includes a condition that a mass ratio of a total content of the components (A) and (B) to the total content of the components (A), (B), (C) and (D) is 0.10 or more and 0.80 or less.

8. The sulfonate composition according to claim 1, wherein the component (B) is a polyhydric alcohol, and the composition satisfies the following condition (IIa) or the following condition (IIb): condition (IIa): A/(A+B+C+D) is 0.05 or more and 0.71 or less, B/(A+B+C+D) is more than 0.05 and 0.90 or less, C/(A+B+C+D) is more than 0 and less than 0.001, and D/(A+B+C+D) is more than 0.10 and less than 0.50; condition (IIb): A/(A+B+C+D) is 0.05 or more and 0.71 or less, B/(A+B+C+D) is more than 0.05 and less than 0.40, C/(A+B+C+D) is 0.001 or more, and D/(A+B+C+D) is 0.13 or more and less than 0.50.

9. The sulfonate composition according to claim 8, wherein the composition satisfies the condition (IIa), which further includes a condition that a mass ratio of a total content of the components (A) and (B) to the total content of the components (A), (B), (C) and (D) is 0.40 or more and 0.95 or less.

10. The sulfonate composition according to claim 8, wherein the composition satisfies the condition (IIb), which further includes a condition that a mass ratio of a total content of the components (A) and (B) to the total content of the components (A), (B), (C) and (D) is 0.40 or more and 0.95 or less.

11. The sulfonate composition according to claim 1, wherein A/(A+B+C+D) is 0.3 or more.

12. The sulfonate composition according to claim 1, wherein A/(A+B+C+D) is 0.4 or more.

13. The sulfonate composition according to claim 1, wherein A/(A+B+C+D) is 0.5 or more.

14. The sulfonate composition according to claim 1, wherein C/(A+B+C+D) is less than 0.018.

15. The sulfonate composition according to claim 1, wherein C/(A+B+C+D) is less than 0.016.

16. The sulfonate composition according to claim 1, wherein D/(A+B+C+D) is 0.13 or more.

17. The sulfonate composition according to claim 1, wherein a mass ratio of the content of the component (C) to the component (A), C/A, is 0.020 or less.

18. The sulfonate composition according to claim 1, wherein the component (B) is a compound selected from the group consisting of methanol, ethanol, 1-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 1-octanol, 1-nonanol, 2-nonanol, 5-nonanol, 1-decanol, 1-dodecanol, 3,5,5-trimethylhexan-1-ol, 2,6-dimethyl-4-heptanol, 2-propylheptanol, 4-methyl 2-propylhexanol, and 5-methyl 2- propylhexanol.

19. The sulfonate composition according to claim 1, wherein the component (B) is a compound selected from the group consisting of ethylene glycol, propylene glycol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,10-decanediol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, tripropylene glycol, glycerin, xylitol, and sorbitol.

20. The sulfonate composition according to claim 1, wherein the component (B) is a compound selected from the group consisting of ethanol, 1-butanol, 1-propanol, glycerin, and propylene glycol.

21. The sulfonate composition according to claim 1, wherein the total content of the components (A), (B), (C) and (D) in the sulfonate composition is 90 mass % or more and 100 mass % or less.

Description

EXAMPLES

[0266] The content of each component in the react products of the production examples described later and the compositions in Examples was determined by each of the following methods:

(I) Sodium Sulfosuccinate Ester Content (mass %) [0267] it was determined in accordance with the test method for synthetic detergents in JIS K 3362;
(II) Maleic Acid Diester Content (mass %) [0268] a maleic acid diester was quantified by gas chromatography;
(III) Ethanol Content (mass %) [0269] ethanol was quantified by gas chromatography;
(IV) Propylene Glycol Content (mass %) [0270] propylene glycol was quantified by gas chromatography;
(V) Water Content (mass %) [0271] it was determined in accordance with Test methods for water content of chemical products in JIS K 0068;
(VI) Sodium Sulfate Content (mass %) [0272] sodium sulfate was quantified using “automatic potentiometric titrator” manufactured by Kyoto Electronics Manufacturing Co., Ltd.; and
(VII) Sodium Sulfite Content (mass %) [0273] sodium sulfite was quantified using “ICS-2100” manufactured by Thermo Fisher Scientific.

Production Example 1

[0274] A maleic acid diester was obtained in conformance with Example 2 of US-A 2007/0214999.

[0275] Next, the maleic acid diester (100 parts by mass), sodium disulfite (26.4 parts by mass), ion exchange water (17.3 carts by mass) and ethanol (35.5 parts by mass) were put in a 1-h glass reaction vessel, and reacted at 115° C. in a publicly-known manner. The mixture was cooled to 60° C. or less, and after the residual sodium hydrogen sulfite was oxidized with 30% hydrogen peroxide water, the pH was adjusted to 5 with a 10% aqueous sodium hydroxide solution. Subsequently, the solvents a sodium sulfate were removed by filtration, distillation under reduced pressure, freeze drying or the like to obtain a reaction product including a sodium sulfosuccinate ester. In this reaction product, the sodium sulfosuccinate ester content: 96.4 mass %, a maleic acid diester: 1.5 mass %, the loss on drying: 1.2 mass % and the sodium sulfate content: 0.07 mass %. The sodium sulfosuccinate ester included in this reaction product was a compound of the formula (1) in which N represents a sodium ion, p and q each represent 0, and R and R′ each represent 2-propylheptyl group [hereinafter referred to as sodium sulfosuccinate ester (1)]. Further, the maleic acid diester included in this reaction product was a compound of the formula (2) which m and n each represent 0, and R and R′ each represent 2-propylheptyl group.

Production Example 2

[0276] A maleic acid diester was obtained in conformance with Example 2 of US-A 2007/0214999.

[0277] Next, sodium sulfosuccinate ester (2) was obtained in conformance with Production Example 2 of JP-A 2002-224552, provided that alkylene oxide adduct (E-1) in that Production Example 2 was not used, and the diesterized product was replaced with the above maleic acid diester. The reaction time for sulfonation was then adjusted to obtain reaction products with different amounts of residual sodium sulfate and sodium sulfite. The sodium sulfosuccinate ester included in each of these reaction products was a compound of the formula (1) in which M represents a sodium ion, p and q each represent 0, and R and R′ each represent 2-propylheptyl group [hereinafter referred to as sodium sulfosuccinate ester (2)].

Examples 1 to 5 and Comparative Examples 1 to 2

(1) Sulfonate Composition

[0278] The sulfonate compositions having any of the compositions in Tables 1 to 5 were each prepared by mixing the reaction product obtained in production example 1 or 2 and water. The components listed below were then added as necessary to adjust the content. Further, the reaction product produced in production example 1 was used in the form of a composition obtained by drying it when formulating the sulfonate compositions. Further, the reaction product produced in production example 2 was used as-is when formulating the sulfonate compositions. [0279] Ethanol: manufactured by FUJIFILM Wako Pure Chemical Corporation, a special grade reagent [0280] Propylene glycol: manufactured by FUJIFILM Wako Pure Chemical Corporation, a special grade reagent [0281] Sodium sulfate: manufactured by FUJIFILM Wako Pure Chemical Corporation, a special grade reagent

(2) Evaluation

(2-1) Evaluation of Uniformity

[0282] 30 g of each sulfonate composition prepared was put in a tightly-sealable glass vessel (with a capacity of 50 cc), and after the vessel was sealed tightly, the sample was left to stand for 24 hours in a thermostatic bats whose temperature was kept constant under each temperature condition (25° C., 35° C., 40° C. or 60° C.), and the appearance and fluidity of the sample were thereafter observed. The results are shown in the tables.

(2-2) Evaluation of Freezing Recoverability

[0283] 30 g of each sulfonate composition prepared was in a tightly-sealable glass vessel (with a capacity of 50 cc), and with the vessel sealed tightly, the sample was stored (completely solidified) in a freezer at 0° C. or less for 24 hours. Subsequently, after confirmed to have turned to a liquid state in a thermostatic bath whose temperature was kept constant at 40° C., the sample was left to stand for 2 hours, and the appearance of the sample was thereafter observed. The results are shown in the tables.

TABLE-US-00001 TABLE 1 Example 1 1-1 1-2 1-3 1-4 1-5 Sulfosuccinate Composition (A) Sodium 65 60 70 70 60 ester (mass %) sulfosuccinate composition ester (1)*.sup.1 (B) Ethanol 10 20 10 15 10 (C) Sodium sulfate 0.05 0.05 0.05 0.05 0.04 (D) Ion exchange 23.95 19.05 18.85 13.85 29.0 water (Y) Maleic acid 1.0 0.9 1.1 1.1 0.9 diester*.sup.1 Total amount 100 100 100 100 100 A/(A + B + C + D) (mass ratio) 0.66 0.61 0.71 0.71 0.61 B/(A + B + C + D) (mass ratio) 0.10 0.20 0.10 0.15 0.10 C/(A + B + C + D) (mass ratio) 0.0005 0.0005 0.0005 0.0005 0.0004 D/(A + B + C + D) (mass ratio) 0.24 0.19 0.19 0.14 0.29 (A + B)/(A + B + C + D) (mass ratio) 0.76 0.81 0.81 0.86 0.71 Uniformity 25° C. Clear liquid Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no state, no precipitation precipitation precipitation precipitation precipitation 35° C. Clear liquid Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no state, no precipitation precipitation precipitation precipitation precipitation 40° C. Clear liquid Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no state, no precipitation precipitation precipitation precipitation precipitation 60° C. Clear liquid Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no state, no precipitation precipitation precipitation precipitation precipitation Freezing recoverability Clear liquid Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no state, no precipitation precipitation precipitation precipitation precipitation Example 1 1-6 1-7 1-8 1-9 1-10 Sulfosuccinate Composition (A) Sodium 50 50 40 40 30 ester (mass %) sulfosuccinate composition ester (1)*.sup.1 (B) Ethanol 10 30 10 30 20 (C) Sodium sulfate 0.04 0.04 0.03 0.03 0.02 (D) Ion exchange 39.2 19.2 49.3 29.3 49.5 water (Y) Maleic acid 0.8 0.8 0.6 0.6 0.5 diester*.sup.1 Total amount 100 100 100 100 100 A/(A + B + C + D) (mass ratio) 0.50 0.50 0.40 0.40 0.30 B/(A + B + C + D) (mass ratio) 0.10 0.30 0.10 0.30 0.20 C/(A + B + C + D) (mass ratio) 0.0004 0.0004 0.0003 0.0003 0.0002 D/(A + B + C + D) (mass ratio) 0.39 0.19 0.50 0.30 0.50 (A + B)/(A + B + C + D) (mass ratio) 0.60 0.81 0.50 0.70 0.50 Uniformity 25° C. Clear liquid Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no state, no precipitation precipitation precipitation precipitation precipitation 35° C. Clear liquid Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no state, no precipitation precipitation precipitation precipitation precipitation 40° C. Clear liquid Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no state, no precipitation precipitation precipitation precipitation precipitation 60° C. Clear liquid Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no state, no precipitation precipitation precipitation precipitation precipitation Freezing recoverability Clear liquid Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no state, no precipitation precipitation precipitation precipitation precipitation *.sup.1The reaction product of production example 1 was used.

TABLE-US-00002 TABLE 2 Example 2 2-1 2-2 2-3 2-4 Sulfosuccinate Composition (A) Sodium 70 68 65 60 ester (mass %) sulfosuccinate composition ester (1)*.sup.1 (B) Ethanol 9 10 5 10 (C) Sodium sulfate 0.3 0.3 1.0 1.0 (D) Ion exchange 19.6 20.6 28.0 28.1 water (Y) Maleic acid 1.1 1.1 1.0 0.9 diester*.sup.1 Total amount 100 100 100 100 A/(A + B + C + D) (mass ratio) 0.71 0.69 0.66 0.61 B/(A + B + C + D) (mass ratio) 0.09 0.10 0.05 0.10 C/(A + B + C + D) (mass ratio) 0.0030 0.0030 0.0101 0.0101 D/(A + B + C + D) (mass ratio) 0.20 0.21 0.28 0.28 (A + B)/(A + B + C + D) (mass ratio) 0.799 0.789 0.707 0.706 Uniformity 25° C. Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no precipitation precipitation precipitation precipitation 35° C. Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no precipitation precipitation precipitation precipitation 40° C. Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no precipitation precipitation precipitation precipitation 60° C. Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no precipitation precipitation precipitation precipitation Freezing recoverability Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no precipitation precipitation precipitation precipitation Example 2 Comparative example 1 2-5 1-1 1-2 Sulfosuccinate Composition (A) Sodium 65 75 76 ester (mass %) sulfosuccinate composition ester (1)*.sup.1 (B) Ethanol 10 20 4 (C) Sodium sulfate 1.0 0.3 0.3 (D) Ion exchange 23.0 3.5 18.5 water (Y) Maleic acid 1.0 1.2 1.2 diester*.sup.1 Total amount 100 100 100 A/(A + B + C + D) (mass ratio) 0.66 0.76 0.77 B/(A + B + C + D) (mass ratio) 0.10 0.20 0.04 C/(A + B + C + D) (mass ratio) 0.0101 0.0030 0.0030 D/(A + B + C + D) (mass ratio) 0.23 0.04 0.19 (A + B)/(A + B + C + D) (mass ratio) 0.758 0.962 0.810 Uniformity 25° C. Clear liquid Turbidity, Turbidity, state, no precipitation precipitation precipitation 35° C. Clear liquid Turbidity, Turbidity, state, no precipitation precipitation precipitation 40° C. Clear liquid Turbidity, Turbidity, state, no precipitation precipitation precipitation 60° C. Clear liquid Turbidity, Turbidity, state, no precipitation precipitation precipitation Freezing recoverability Clear liquid Turbidity, Turbidity, state, no precipitation precipitation precipitation *.sup.1The reaction product of production example 1 was used.

TABLE-US-00003 TABLE 3 Example 3 3-1 3-2 3-3 3-4 3-5 Sulfosuccinate Composition (A) Sodium 65 60 70 70 50 ester (mass %) sulfosuccinate composition ester (1)*.sup.1 (B) Propylene glycol 10 20 10 15 33 (C) Sodium sulfate 0.05 0.05 0.05 0.05 0.04 (D) Ion exchange 23.95 19.05 18.85 13.85 16.19 water (Y) Maleic acid 1 0.9 1.1 1.1 0.8 diester*.sup.1 Total amount 100 100 100 100 100 A/(A + B + C + D) (mass ratio) 0.66 0.61 0.71 0.71 0.50 B/(A + B + C + D) (mass ratio) 0.10 0.20 0.10 0.15 0.33 C/(A + B + C + D) (mass ratio) 0.0005 0.0005 0.0005 0.0005 0.0004 D/(A + B + C + D) (mass ratio) 0.24 0.19 0.19 0.14 0.16 D/(A + D) (mass ratio) 0.27 0.24 0.21 0.17 0.24 (A + B)/(A + B + C + D) (mass ratio) 0.76 0.81 0.81 0.86 0.84 Uniformity 25° C. Clear liquid Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no state, no precipitation precipitation precipitation precipitation precipitation 35° C. Clear liquid Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no state, no precipitation precipitation precipitation precipitation precipitation 40° C. Clear liquid Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no state, no precipitation precipitation precipitation precipitation precipitation 60° C. Clear liquid Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no state, no precipitation precipitation precipitation precipitation precipitation Freezing recoverability Clear liquid Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no state, no precipitation precipitation precipitation precipitation precipitation Example 3 3-6 3-7 3-8 3-9 Sulfosuccinate Composition (A) Sodium 50 40 40 30 ester (mass %) sulfosuccinate composition ester (1)*.sup.1 (B) Propylene glycol 10 40 15 50 (C) Sodium sulfate 0.04 0.03 0.03 0.02 (D) Ion exchange 39.19 19.35 44.35 19.52 water (Y) Maleic acid 0.8 0.6 0.6 0.5 diester*.sup.1 Total amount 100 100 100 100 A/(A + B + C + D) (mass ratio) 0.50 0.40 0.40 0.30 B/(A + B + C + D) (mass ratio) 0.10 0.40 0.15 0.50 C/(A + B + C + D) (mass ratio) 0.0004 0.0003 0.0003 0.0002 D/(A + B + C + D) (mass ratio) 0.39 0.19 0.45 0.20 D/(A + D) (mass ratio) 0.44 0.33 0.53 0.39 (A + B)/(A + B + C + D) (mass ratio) 0.60 0.80 0.55 0.80 Uniformity 25° C. Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no precipitation precipitation precipitation precipitation 35° C. Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no precipitation precipitation precipitation precipitation 40° C. Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no precipitation precipitation precipitation precipitation 60° C. Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no precipitation precipitation precipitation precipitation Freezing recoverability Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no precipitation precipitation precipitation precipitation Example 3 3-10 3-11 3-12 3-13 Sulfosuccinate Composition (A) Sodium 30 5 5 5 ester (mass %) sulfosuccinate composition ester (1)*.sup.1 (B) Propylene glycol 20 75 90 50 (C) Sodium sulfate 0.02 0.004 0.004 0.004 (D) Ion exchange 49.52 19.92 4.92 44.92 water (Y) Maleic acid 0.5 0.1 0.1 0.1 diester*.sup.1 Total amount 100 100 100 100 A/(A + B + C + D) (mass ratio) 0.30 0.05 0.05 0.05 B/(A + B + C + D) (mass ratio) 0.20 0.75 0.90 0.50 C/(A + B + C + D) (mass ratio) 0.0002 0.00004 0.00004 0.00004 D/(A + B + C + D) (mass ratio) 0.50 0.20 0.05 0.45 D/(A + D) (mass ratio) 0.62 0.80 0.50 0.90 (A + B)/(A + B + C + D) (mass ratio) 0.50 0.80 0.95 0.55 Uniformity 25° C. Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no precipitation precipitation precipitation precipitation 35° C. Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no precipitation precipitation precipitation precipitation 40° C. Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no precipitation precipitation precipitation precipitation 60° C. Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no precipitation precipitation precipitation precipitation Freezing recoverability Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no precipitation precipitation precipitation precipitation *.sup.1The reaction product of production example 1 was used.

TABLE-US-00004 TABLE 4 Example 4 4-1 4-2 4-3 4-4 4-5 Sulfosuccinate Composition (A) Sodium 70 65 65 60 70 ester (mass %) sulfosuccinate composition ester (1)*.sup.1 (B) Propylene glycol 10 10 15 15 15 (C) Sodium sulfate 0.3 1 1 1 0.30 (D) Ion exchange 18.6 23 18 23.1 13.2 water (Y) Maleic acid 1.1 1 1 0.9 1.5 diester*.sup.1 Total amount 100 100 100 100 100 A/(A + B + C + D) (mass ratio) 0.71 0.66 0.66 0.61 0.71 B/(A + B + C + D) (mass ratio) 0.10 0.10 0.15 0.15 0.15 C/(A + B + C + D) (mass ratio) 0.0030 0.0101 0.0101 0.0101 0.0030 D/(A + B + C + D) (mass ratio) 0.19 0.23 0.18 0.23 0.13 D/(A + D) (mass ratio) 0.21 0.26 0.22 0.28 0.16 (A + B)/(A + B + C + D) (mass ratio) 0.81 0.76 0.81 0.76 0.86 Uniformity 25° C. Clear liquid Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no state, no precipitation precipitation precipitation precipitation precipitation 35° C. Clear liquid Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no state, no precipitation precipitation precipitation precipitation precipitation 40° C. Clear liquid Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no state, no precipitation precipitation precipitation precipitation precipitation 60° C. Clear liquid Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no state, no precipitation precipitation precipitation precipitation precipitation Freezing recoverability Clear liquid Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no state, no precipitation. precipitation precipitation precipitation precipitation Example 4 4-6 4-7 4-8 4-9 Sulfosuccinate Composition (A) Sodium 60 50 60 50 ester (mass %) sulfosuccinate composition ester (1)*.sup.1 (B) Propylene glycol 12.9 10.7 20 25 (C) Sodium sulfate 0.25 0.21 0.25 0.21 (D) Ion exchange 25.6 38.0 18.5 23.7 water (Y) Maleic acid 1.3 1.1 1.3 1.1 diester*.sup.1 Total amount 100 100 100 100 A/(A + B + C + D) (mass ratio) 0.61 0.51 0.61 0.51 B/(A + B + C + D) (mass ratio) 0.13 0.11 0.20 0.25 C/(A + B + C + D) (mass ratio) 0.0026 0.0021 0.0026 0.0021 D/(A + B + C + D) (mass ratio) 0.26 0.38 0.19 0.24 D/(A + D) (mass ratio) 0.30 0.43 0.24 0.32 (A + B)/(A + B + C + D) (mass ratio) 0.74 0.61 0.81 0.76 Uniformity 25° C. Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no precipitation precipitation precipitation precipitation 35° C. Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no precipitation precipitation precipitation precipitation 40° C. Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no precipitation precipitation precipitation precipitation 60° C. Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no precipitation precipitation precipitation precipitation Freezing recoverability Clear liquid Clear liquid Clear liquid Clear liquid state, no state, no state, no state, no precipitation precipitation precipitation precipitation Example 4 Comparative example 2 4-10 4-11 2-1 2-2 Sulfosuccinate Composition (A) Sodium 40 35 75 76 ester (mass %) sulfosuccinate composition ester (1)*.sup.1 (B) Propylene glycol 30 32.5 20 4 (C) Sodium sulfate 0.17 0.15 0.3 0.3 (D) Ion exchange 29.0 31.6 3.5 18.5 water (Y) Maleic acid 0.8 0.7 1.2 1.2 diester*.sup.1 Total amount 100 100 100 100 A/(A + B + C + D) (mass ratio) 0.40 0.35 0.76 0.77 B/(A + B + C + D) (mass ratio) 0.30 0.33 0.20 0.04 C/(A + B + C + D) (mass ratio) 0.0017 0.0015 0.0030 0.0030 D/(A + B + C + D) (mass ratio) 0.29 0.32 0.04 0.19 D/(A + D) (mass ratio) 0.42 0.47 0.04 0.20 (A + B)/(A + B + C + D) (mass ratio) 0.71 0.68 0.96 0.81 Uniformity 25° C. Clear liquid Clear liquid Turbidity, No fluidity state, no state, no precipitation precipitation precipitation 35° C. Clear liquid Clear liquid Turbidity, No fluidity state, no state, no precipitation precipitation precipitation 40° C. Clear liquid Clear liquid Turbidity, No fluidity state, no state, no precipitation precipitation precipitation 60° C. Clear liquid Clear liquid Turbidity, No fluidity state, no state, no precipitation precipitation precipitation Freezing recoverability Clear liquid Clear liquid Turbidity, No fluidity state, no state, no precipitation precipitation precipitation *.sup.1The reaction product of production example 1 was used.

TABLE-US-00005 TABLE 5 Example 5 5-1 5-2 Sulfosuccinate Composition (A) Sodium sulfosuccinate ester (2)*.sup.2 65 65 ester (mass %) (B) Propylene glycol 15 15 composition (C) Sodium sulfate 0.3 0.5 Sodium sulfite 0.05 0.3 (D) Ion exchange water 17.95 17.1 (Y) Maleic acid diester*.sup.2 1.7 2.1 Total amount 100 100 A/(A + B + C + D) (mass ratio) 0.66 0.66 B/(A + B + C + D) (mass ratio) 0.15 0.15 C/(A + B + C + D) (mass ratio) 0.004 0.008 D/(A + B + C + D) (mass ratio) 0.18 0.17 D/(A + D) (mass ratio) 0.22 0.21 (A + B)/(A + B + C + D) (mass ratio) 0.46 0.47 Uniformity 25° C. Clear liquid state, Clear liquid state, no precipitation no precipitation 35° C. Clear liquid state, Clear liquid state, no precipitation no precipitation 40° C. Clear liquid state, Clear liquid state, no precipitation no precipitation 60° C. Clear liquid state, Clear liquid state, no precipitation no precipitation Freezing recoverability Clear liquid state, Clear liquid state, no precipitation no precipitation *.sup.2The reaction product of production example 2 was used.