SOFTENING BASE AGENT

Abstract

The present invention is a softening base agent containing a compound represented by the following formula 1:

##STR00001## wherein each of R.sup.1 and R.sup.2 represents a hydrocarbon group with 6 or more and 24 or less carbons, and the total number of carbons in R.sup.1 and R.sup.2 is 18 or more and 30 or less; and M is a cation, excluding a hydrogen ion.

Claims

1. A softening base agent comprising a compound according to formula 1: ##STR00005## wherein: each of R.sup.1 and R.sup.2 is independently a hydrocarbon group with 6 to 24 carbons; a total number of carbons in R.sup.1 and R.sup.2 is 18 to 30; and M is a cation, excluding a hydrogen ion.

2. The softening base agent according to claim 1, wherein at least one of R.sup.1 and R.sup.2 is a hydrocarbon group having a branched structure or an unsaturated bond.

3. The softening base agent according to claim 2, wherein: at least one of R.sup.1 and R.sup.2 is a hydrocarbon group having a branched structure; the hydrocarbon group having a branched structure has a branched chain in a second position; and the branched chain is a hydrocarbon group with 2 or more carbons.

4. The softening base agent according to claim 1, wherein each of R.sup.1 and R.sup.2 is independently a hydrocarbon group with 6 to 17 carbons.

5. The softening base agent according to claim 1, wherein the agent comprises: a first compound according to formula 1 in which R.sup.1 and R.sup.2 are hydrocarbon groups having the same structure; and a second compound according to formula 1 in which R.sup.1 and R.sup.2 are hydrocarbon groups having different structures.

6. The softening base agent according to claim 1, wherein: each of R.sup.1 and R.sup.2 independently comprises a hydrocarbon group having a branched structure; and a proportion of hydrocarbon groups of R.sup.1 and R.sup.2 according to formula 4 among all hydrocarbon groups R.sup.1 and R.sup.2 in compounds according to formula 1 is 50 mol % or less:
—R.sup.41—CH(CH.sub.3)—R.sup.42  Formula 4 wherein: R.sup.41 is a linear hydrocarbon group with 3 or more carbons; R.sup.42 is a hydrocarbon group; and a total number of carbons in R.sup.41 and R.sup.42 is 4 to 22.

7. A fiber treatment agent composition comprising the softening base agent according to claim 1.

8. The fiber treatment agent composition according to claim 7, wherein a content of the compound according to formula 1 is 1 mass % to 90 mass % based on a total mass of the composition.

9. A method for treating fibers comprising, treating the fibers with the softening base agent according to claim 1, wherein the compound according to formula 1 is applied in an amount of 0.01% o.w.f. to 5% o.w.f relative to the fibers.

10. The method for treating fibers according to claim 9, wherein treating the fibers comprises treating with a treatment liquid obtained by mixing the softening base agent with water having a hardness of 0° DH to 30° DH.

11. The method for treating fibers according to claim 9, wherein the fibers are fabric.

12. The method for treating fibers according to claim 9, wherein treating the fibers comprises treating in a washing process.

13-15. (canceled)

16. The softening base agent according to claim 2, wherein: at least one of R.sup.1 and R.sup.2 is a hydrocarbon group having a branched structure; and the hydrocarbon group having a branched structure has a branched chain derived from a Guerbet alcohol in a second position.

17. The softening base agent according to claim 2, wherein: at least one of R.sup.1 and R.sup.2 is a hydrocarbon group having a branched structure; and the hydrocarbon group having a branched structure has a branched chain derived from a Guerbet alcohol only in a second position.

18. The softening base agent according to claim 1, wherein the total number of carbons in R.sup.1 and R.sup.2 is 20 to 25.

19. The fiber treatment agent composition according to claim 7, wherein a content of softening base agents other than the compound according to formula 1 in the composition is less than 1 mass %.

20. The fiber treatment agent composition according to claim 7, wherein a content of softening base agents other than the compound according to formula 1 in the composition is less than 0.1 mass %.

21. The fiber treatment agent composition according to claim 7, wherein a ratio of a mass of softening base agents other than the compound according to formula 1 to a mass of the compound of according to formula 1 in the composition is 4.5 or less.

22. The fiber treatment agent composition according to claim 7, wherein a ratio of a mass of softening base agents other than the compound according to formula 1 to a mass of the compound of according to formula 1 in the composition is 1.0 or less.

23. The method for treating fibers according to claim 9, wherein treating the fibers comprises treating with a treatment liquid obtained by mixing the softening base agent with water having a hardness of 1° DH to 25° DH.

Description

EXAMPLES

Production Examples 1 to 8

[0147] A dialkyl sulfosuccinate of each production example listed in Table 1 was prepared as follows. In the reaction vessel shown in Table 1 equipped with a stirrer, a heating system, a distillation column and a nitrogen/vacuum connection, raw materials and the catalyst listed in Table 1 used to prepare a maleic acid diester were prepared in their respective amounts shown in Table 1, and after nitrogen substitution, reacted under nitrogen bubbling while dewatered at 100 to 130° C. until an acid value was lowered to an amount equivalent to that of p-toluenesulfonic acid. Subsequently, the catalyst was adsorbed to KYOWAAD® 500SH (manufactured by Kyowa Chemical Industry Co., Ltd.) in an amount of 1 mass relative to the total amount of the contents in the reaction vessel. After removing the adsorbent, an excess alcohol was removed by topping, thereby obtaining a maleic acid diester.

[0148] Next, in a 1-L glass reaction vessel, the maleic acid diester obtained above, sodium disulfite and ion exchange water were prepared in their respective amounts shown in Table 1, and using an alcohol polar solvent such as ethanol or the like to improve the compatibility of raw materials used to prepare each dialkyl sulfosuccinate listed in Table 1, reacted at 115° C. by a publicly-known method until it was confirmed by NMR that a double bond derived from the maleic acid diester disappeared. The reaction product was cooled to 50 to 65° C. and the remaining sodium hydrogen sulfite was oxidized with 30% hydrogen peroxide, and thereafter the pH was adjusted to 5 with 10% NaOH. The solvent and sodium sulfate were removed by distillation under reduced pressure, re-precipitation, liquid separation or the like, thereby obtaining each dialkyl sulfosuccinate listed in Table 1.

TABLE-US-00001 TABLE 1 Production Production Production Production Production example 1 example 2 example 3 example 4 example 5 Dialkyl sulfosuccinate Di(2-propylheptyl) Di(2-butyloctyl)- Dodecyl/2- Octyl/cetyl- Dodecyl/3- sulfosuccinate sulfosuccinate butyloctyl- sulfosuccinate nonethyl- sulfosuccinate sulfosuccinate Preparation Reaction Type Four neck Four neck Four neck Four neck Four neck of maleic vessel flask flask flask flask flask acid diester Capacity 2 L 2 L 500 mL 500 mL 500 mL Raw Maleic Preparation 176.5 g 176.5 g 58.8 g 58.8 g 68.6 g material anhydride amount (g) Preparation 1.8 mol 1.8 mol 0.60 mol 0.60 mol 0.70 mol amount (mol) Alcohol 1 Type 2- 2- 2- Octanol Dodecanol propylheptanol bulytoctanol butyloctanol Preparation 626.6 g 737.8 g 123.0 g 86.0 g 143.5 g amount (g) Preparation 4.0 mol 4.0 mol 0.66 mol 0.66 mol 0.77 mol amount (mol) Alcohol 2 Type — — Dodecanol Cetanol Cis-3- nonene-1-ol Preparation — — 123.0 g 160.0 g 109.5 g amount (g) Preparation — — 0.66 mol 0.66 mol 0.77 mol amount (mol) Catalyst p-toluene- Preparation 2.5 g 2.5 g 0.82 g 0.82 g 0.84 g sulfonic amount (mol) acid mono- Preparation 0.013 mol 0.013 mol 0.0043 mol 0.0043 mol 0.0044 mol hydrate amount (mol) Preparation Raw Maleic acid Preparation 278 g 200 g 150 g 150 g 150 g of dialkyl material diester amount (g) sulfosuccinate Preparation 0.70 mol 0.44 mol 0.33 mol 0.31 mol 0.37 mol amount (mol) Sodium Preparation 73 g 46 g 35 g 32 g 38 g disulfite amount (g) Preparation 0.38 mol 0.24 mol 0.18 mol 0.17 mol 0.20 mol amount (mol) Ion exchange Preparation 48 g 18 g 13 g 12 g 14 g water amount (g) Preparation 2.7 mol 1.0 mol 0.73 mol 0.68 mol 0.81 mol amount (mol) Production Production Production example 6 example 7 example 8 Dialkyl sulfosuccinate Dicetyl Stearyl/oleyl- Cetyl/stearyl- sulfosuccinate sulfosuccinate sulfosuccinate Preparation Reaction Type Four neck Four neck Four neck of maleic vessel flask flask flask acid diester Capacity 2 L 500 mL 500 mL Raw Maleic Preparation 138 g 49.0 g 49.0 g material anhydride amount (g) Preparation 1.4 mol 0.50 mol 0.50 mol amount (mol) Alcohol 1 Type Cetanol Oleyl Cetanol alcohol Preparation 749 g 147.7 g 133.3 g amount (g) Preparation 3.1 mol 0.55 mol 0.55 mol amount (mol) Alcohol 2 Type — Stearyl Stearyl alcohol alcohol Preparation — 148.8 g 148.8 g amount (g) Preparation — 0.55 mol 0.55 mol amount (mol) Catalyst p-toluene Preparation 2.7 g 0.98 g 0.93 g sulfonic amount (mol) acid mono- Preparation 0.014 mol 0.0052 mol 0.0049 mol hydrate amount (mol) Preparation Raw Maleic acid Preparation 200 g 150 g 150 g of dialkyl material diester amount (g) sulfosuccinate Preparation 0.35 mol 0.24 mol 0.25 mol amount (mol) Sodium Preparation 37 g 25 g 26 g disulfite amount (g) Preparation 0.19 mol 0.13 mol 0.14 mol amount (mol) Ion exchange Preparation 18 g 9.6 g 10 g water amount (g) Preparation 1.0 mol 0.53 mol 0.56 mol amount (mol)

[0149] The components in Table 1 are listed below.

[0150] Maleic anhydride: manufactured by FUJIFILM Wako Pure Chemical Corporation, Wako Special Grade

[0151] 2-propylheptanol: manufactured by FUJIFILM Wako Pure Chemical Corporation, Guaranteed Reagent

[0152] 2-butyloctanol: 2-butyl-1-n-octanol, manufactured by FUJIFILM Wako Pure Chemical Corporation, Guaranteed Reagent

[0153] Octanol: manufactured by Kao Corporation, “KALCOL 0898”

[0154] Dodecanol: manufactured by Kao Corporation, “KALCOL 2098”

[0155] Cetanol: manufactured by Kao Corporation, “KALCOL 6098”

[0156] Oleyl alcohol: manufactured by Alfa Aesar

[0157] Cis-3-nonene-1-ol: manufactured by Tokyo Chemical Industry Co., Ltd.

[0158] Stearyl alcohol: manufactured by Kao Corporation, “KALCOL 8098”

[0159] P-toluenesulfonic acid monohydrate: manufactured by FUJIFILM Wako Pure Chemical Corporation, Guaranteed Reagent

[0160] Sodium disulfite: manufactured by FUJIFILM Wako Pure Chemical Corporation, Guaranteed Reagent

Examples 1 to 5 and Comparative Examples 1 to 5

[0161] Using the dialkyl sulfosuccinates listed in Table 1 as softening base agents, softness and the stability of dispersions were evaluated in the following manner. The results are shown in Table 2. Note that Table 2 shows the structures in the formula 1 of the softening base agents. For compounds that do not qualify as compound 1, structures corresponding to those in the formula 1 are shown for convenience.

[0162] The softening base agents listed in Table 2 are as follows. [0163] Inventive product 1: di(2-propylheptyl)-sulfosuccinate prepared in production example 1 [0164] Inventive product 2: di(2-butyloctyl)-sulfosuccinate prepared in production example 2 [0165] Inventive product 3: dodecyl/2-butyloctyl-sulfosuccinate prepared in production example 3 [0166] Inventive product 4: octyl/cetyl-sulfosuccinate prepared in production example 4 [0167] Inventive product 5: dodecyl/3-nonenyl-sulfosuccinate prepared in production example 5 [0168] Comparative product 1: di(2-ethylhexyl)sulfosuccinate, reagent, DIOCTYLSULFOSUCCINATE (MP Biomedical, Inc.) [0169] Comparative product 2: dicetyl sulfosuccinate prepared in production example 6 [0170] Comparative product 3: stearyl/oleyl-sulfosuccinate prepared in production example 7 [0171] Comparative product 4: cetyl/stearyl-sulfosuccinate prepared in production example 8 [0172] Comparative product 5: α-olefin sulfonate, LIPOLAN PB-800CJ, manufactured by Lion Corporation

[0173] Method for Evaluating Softness

1) Pretreatment of Towel Used for Evaluation

[0174] Towels from which sizing agents or impurities were removed by the following pretreatment were used for evaluation.

[0175] In a fully automatic washing machine (manufactured by Panasonic Corporation, Model No.: NA-F60PB3), 52.22 g of a 10% diluent of a nonionic surfactant (manufactured by Kao Corporation, EMULGEN 108) was added as a detergent to 24 commercially available cotton towels (manufactured by Takei Towel Co., Ltd., TW220, white), and a series of washing processes (water volume 50 L, washing for 10 minutes.fwdarw.water-saving rinsing twice.fwdarw.dewatering for 9 minutes) were repeated 3 times using tap water of Wakayama city (the tap water is water having a hardness of 4° DH, and the same applies hereinafter) as water. Subsequently, the series of washing processes were repeated twice using only water. After that, the towels were left and naturally dried at room temperature (25° C.) for 24 hours.

2) Method for Treating Towel

[0176] In National MiniMini Washer NA-35, a predetermined amount of ion exchange water was placed (such that the bath ratio was 25 liters per kilogram of towels) and an aqueous calcium chloride solution (equivalent to 4000° DH) was added to make the hardness 20° DH, and while stirring them, a 5 mass % water dispersion of each softening base agent in Table 2 was added and stirred for 1 minute, and thereafter, 3 cotton towels (about 210 g in total) pretreated in the above 1) were placed therein and treated for 5 minutes under stirring. In this treatment, each softening base agent in Table 2 was used in an amount of 0.5% o.w.f. with reference to 3 cotton towels. Subsequently, the cotton towels were dewatered for 3 minutes in a dewatering tank of a two-tank washing machine (manufactured by TOSHIBA CORPORATION, Model No.: VH-52G(H)), and dried in a thermo-hygrostat at 23° C. and 40% RH for 24 hours. Similarly, an aqueous calcium chloride solution was added to make the hardness 8° DH and a 5 mass % water dispersion of each softening base agent was added in an amount of 0.3% o.w.f. to obtain a treatment liquid, and cotton towels were treated therewith and dried.

3) Softness Evaluation

[0177] A cotton towel treated with a formulation indicated in each score below was prepared as a reference by the methods in the above 1) and 2).

[0178] The softness of a cotton towel treated with each softening base agent listed in Table 2 was compared with that of each reference cotton towel to evaluate the softness. Scores (points) given by five panelists in accordance with the following criteria to make evaluations were averaged and listed in the table. Note that the scores given by the panelists to make evaluations could be decimal fraction values between values of two scores.

[0179] Score 1: as soft as that treated only with tap water at 20° C.

[0180] Score 2: as soft as that treated with a formulation using an indicator softening base agent in an amount of 0.025% o.w.f. in tap water at 20° C.

[0181] Score 3: as soft as that treated with a formulation using the indicator softening base agent in an amount of 0.050% o.w.f. in tap water at 20° C.

[0182] Score 4: as soft as that treated with a formulation using the indicator softening base agent in an amount of 0.075% o.w.f. in tap water at 20° C.

[0183] Score 5: as soft as that treated with a formulation using the indicator softening base agent in an amount of 0.100% o.w.f. in tap water at 20° C.

[0184] Here, an ester amide hydrochloride (2-[N-[3-alkanoyl(C14-20)aminopropyl]-N-methylamino]ethylalkano(C14-20)ate hydrochloride) was used as the indicator softening base agent.

[0185] Method for Evaluating Dispersion Stability

[0186] 5 g of each softening base agent in Table 2 and 95 g of ion exchange water were mixed and stirred at 80° C. for 20 minutes, and thereafter stirred at room temperature (20° C.) for 20 minutes, and left at room temperature for 24 hours. After that, the mixture was further left at 5° C. for 24 hours. The dispersion stability was evaluated by observing the appearance of the mixture. Evaluation criteria for the dispersion stability were shown below. The dispersion stability was evaluated on the basis of the appearance observed at room temperature immediately after stirring at 80° C. for 20 minutes (immediately after preparation) and the appearance observed at a liquid temperature of 5° C. after leaving at 5° C. for 24 hours (after leaving at 5° C. for 24 hours).

[0187] *Evaluation Criteria for Dispersion Stability

[0188] Good: no precipitations

[0189] Average: a slight precipitation

[0190] Poor: a large amount of precipitation

TABLE-US-00002 TABLE 2 Example 1 2 3 4 5 Softening Compound Inventive Inventive Inventive Inventive Inventive base agent product 1 product 2 product 3 product 4 product 5 Structure in R.sup.1, R.sup.2 2-propylheptyl 2-butyloctyl 2-butyloctyl Octyl (linear Dodecyl (linear formula 1 (branched (branched (branched saturated):cetyl saturated):3- saturated) saturated) saturated):dodecyl (linear nonenyl (linear (linear saturated) = saturated) = unsaturated) = 1:1 (molar ratio) 1:1 (molar ratio) 1:1 (molar ratio) Total number of carbons in R.sup.1 20 24 24 24 21 and R.sup.2 (molar average) M Na Na Na Na Na Degree of branching 0.1 0.083 0.042 0 0 Dispersion Immediately after Good Good Good Good Good stability preparation After leaving for 24 Good Good Good Average Good hours at 5° C. Softness 20° DH 3.2 2.9 4.2 4.7 3.4 (point)  8° DH 2.8 2.5 2.5 3.1 2.6 Comparative example 1 2 3 4 5 Softening Compound Comparative Comparative Comparative Comparative Comparative base agent product 1 product 2 product 3 product 4 product 5 Structure R.sup.1, R.sup.2 2-ethylhexyl Cetyl Stearyl (linear Cetyl (linear — in formula 1 (branched (linear saturated):oleyl saturated):stearyl saturated) saturated) (linear unsaturated) = (linear saturated) = 1:1 (molar ratio) 1:1 (molar ratio) Total number of carbons in R.sup.1 16 32 36 34 — and R.sup.2 (motor average) M Na Na Na Na — Degree of branching 0.125 0  0 0 — Dispersion Immediately after Good Good Poor Good Good stability preparation After having for 24 Good Average Poor Poor Good hours at 5° C. Softness 20° DH 1.7 2.3 Not evaluable 1.8 1.7 (point)  8° DH 1.9 2.4   2.4 1.7 1.2

[0191] From the results in Table 2 showing that the inventive softening base agents impart higher softness than the comparative softening base agents, it can be seen that the inventive softening base agents are softening base agents superior to other anionic surfactants in fiber softening effect. Further, it can be seen that the inventive softening base agents exhibit more excellent softness when used with water having a higher hardness. In addition, it can be seen that the inventive softening base agents have excellent dispersion stability in water.