JP6800498B1 - A novel compound and a cleaning composition containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a cleaning agent composition which is used for removing stains adhering to an article and has good detergency and rinsing property, and a compound having excellent low foaming property which gives the cleaning agent composition. The compound of the present invention is represented by the following general formula (1). HO-R1-O-A1-H (1) (In the formula, R1 is an alkylene group having 6 to 14 carbon atoms, and A1 is a divalent group represented by-(R5O) S-. R5 is an alkylene group having 2 or 3 carbon atoms, s is an integer of 1 to 10, and when s is 2 or more, R5 in-(R5O) S- is different even if they are all the same. (May be.) [Selection diagram] Fig. 1

Description

The present invention relates to a novel compound and a cleaning agent composition containing the same and having excellent detergency.

Conventionally, a diol compound having a hydroxy group at both ends and a plurality of -RO- groups (R is an ethylene group or an alkylene group) between them has been used as one of the raw material components of a cleaning agent composition, a pesticide composition and the like. It is used.

For example, Patent Document 1 discloses a spreading agent for a water-floating pesticide composition containing a diol compound represented by the following formula.
HO-A ^1- OR-O-A ^2- OH
(R is a residue obtained by removing all hydroxyl groups from an alkanediol having 6 to 14 carbon atoms, and A ¹ and A ² are composed of 1 to 7 oxyalkylene units having 2 to 4 carbon atoms (poly). Residues obtained by removing all hydroxyl groups from (poly) alkylene glycol having an oxyalkylene group)

Further, Patent Document 2 discloses a liquid cleansing composition used for body shampoos, facial cleansers, hair shampoos and the like, which contains a polyoxyethylene alkyl ether type nonionic surfactant represented by the following formula. There is.
R ^1- O- (CH ₂ CH ₂ O) _n- H
(R ¹ represents a linear or branched alkyl or alkenyl group having 10 to 14 carbon atoms, and n represents a number of 85 to 150).

By the way, in order to remove stains adhering to articles such as tableware and clothes by a dishwasher, a washing machine and the like, a cleaning agent composition mainly containing a surfactant is used. Some of the cleaning agent compositions generate a lot of bubbles, and if the bubbles overflow inside the cleaning device, the cleaning property may be deteriorated. Therefore, a cleaning agent composition having low foaming property (hereinafter referred to as "low foaming property") has been studied without using an additive such as an antifoaming agent in combination.
Patent Document 3 describes an anionic surfactant composed of two specific sulfonates, an aromatic sulfonic acid, an aromatic sulfonic acid, an aromatic carboxylic acid, an aromatic carboxylic acid salt, and 2 to 2 carbon atoms. A liquid cleaning agent containing at least one selected from the group consisting of 4 alcohols, which has good low temperature stability and has an effect of quick foaming is disclosed.

Japanese Unexamined Patent Publication No. 2007-39344 Japanese Unexamined Patent Publication No. 2016-193979 Japanese Unexamined Patent Publication No. 2012-23307

An object of the present invention is to provide a cleaning agent composition which is used for removing stains adhering to an article and has good detergency and rinsing property, and a compound having excellent low foaming property which gives the same.

The compound of the present invention (hereinafter referred to as "diol compound") is characterized by being represented by the following general formula (1).
HO-R ^1- O-A ^1- H (1)
(In the formula, R ¹ is a branched alkylene group selected from any of the following formulas (5) to (7) , and A ¹ is a divalent group represented by − (R ⁵ O) _S −. in and, ^{R 5} is an alkylene group having 2 or 3 carbon atoms, s is an integer of ^{3 ~ 6, - (R 5} O) S - be all ^{R 5} are the same in, or different May be.)

The cleaning agent composition of the present invention is characterized by containing the above-mentioned diol compound of the present invention.
In addition, the cleaning agent composition of the present invention also includes the following aspects.
A low-foaming detergent composition containing a compound represented by the following general formula (11), an anionic surfactant, and a chelating agent, wherein the anionic surfactant is a salt of alkylbenzene sulfonic acid. , And a cleaning agent composition comprising an alkyl ether sulfate of polyoxyethylene or polyoxyalkylene .
HO-R ^1- O-A ^1- H (11)
(In the formula, R ¹ is an alkylene group having 8 to 12 carbon atoms, A ¹ is a divalent group represented by − (R ⁵ O) _S −, and R ⁵ has 2 carbon atoms. or 3 alkylene group, s is an integer from 3 to 6, - ^(R 5 _{O) S} - in ^{R 5} is also all be identical or may be different).

The diol compound of the present invention has excellent low foaming properties and is suitable as a raw material component of a cleaning agent composition that removes stains adhering to articles. The cleaning agent composition of the present invention not only preferably removes stains adhering to an article, but also has excellent rinsability after cleaning and is economical.

6 is an LC-MS spectrum of the diol compound obtained in Synthesis Example 1.

The diol compounds comprising the present invention, a compound represented by the following general formula (1), only at one end side, compounds thereof having an oxy ethylene units and / or oxypropylene units (poly) oxyalkylene group Be done .
HO-R ^1- O-A ^1- H (1)
(In the formula, R ¹ is an alkylene group having 6 to 14 carbon atoms, A ¹ is a divalent group represented by − (R ⁵ O) _S −, and R ⁵ has 2 carbon atoms. or 3 alkylene group, s represents an integer of 1 to 10, when s is 2 or _{^{more, - (R 5 O) S}} - all ^{R 5} are in may be the same or different. )

In the present invention, Keru Contact by the general formula (1), the structure of the alkylene groups R ¹ are shown below, a branched alkylene group selected from any one of the following formulas (5) to (7).

In the general formula (1), the alkylene group R ⁵ which constitutes the A ¹ is an alkylene group having a carbon number of 2 or 3, i.e., an ethylene group or a linear or branched propylene group. Therefore, A ¹ contains an oxyethylene group (-C ₂ H ₄ O-) or an oxypropylene group (-C ₃ H ₆ O-).
In the diol compound of the present invention, s, which is the total number of oxyethylene groups or oxypropylene groups, is 3 to 6 , preferably 3 to 5. _- (R 5 ^O) S - be all R ⁵ are the same in, may be different, if it contains both oxyethylene groups and oxypropylene groups, these groups regularly or irregularly It has a continuous and connected structure.

Conventionally, in a surfactant contained in a known cleaning agent composition, the degree of defoaming property when an aqueous solution is foamed varies. In the diol compound of the present invention, when the difference in surface tension between the aqueous solution in the static region where the surface tension has almost reached equilibrium and the one in the dynamic region is calculated, the calculated value is small. It tends to be. This is because many diol compounds are oriented at the interface between water and the outside world in the dynamic region, and as a result, it is presumed that the diol compound is excellent in low foaming property.

The method for producing the diol compound containing the present invention is not particularly limited. A preferred production method comprises a step of reacting an alkanediol having 6 to 14 carbon atoms with at least one selected from ethylene oxide and propylene oxide in the presence of a catalyst (hereinafter, referred to as “reaction step”). This is a method (hereinafter referred to as “first manufacturing method”). Hereinafter, this first manufacturing method will be described.

Examples of the alkanediol include linear alkanediols such as hexanediol, heptanediol, octanediol, nonanediol, decanediol, undecanediol, dodecanediol, tridecanediol, and tetradecanediol; 2-butyl-2-ethyl-1, Examples thereof include branched alkane diols such as 3-propanediol, 2,4-diethyl-1,5-pentanediol and 2-methyl-1,8-octanediol. The alkanediol used in the above reaction step may be only one kind or two or more kinds. The alkanediol used in the present invention includes branched alkanes of 2-butyl-2-ethyl-1,3-propanediol, 2,4-diethyl-1,5-pentanediol, and 2-methyl-1,8-octanediol. Diol is preferred.

A catalyst is used in the above reaction step. This catalyst is not particularly limited, but is preferably a basic compound because a desired product can be efficiently obtained. The basic compound may be either an inorganic compound or an organic compound, and examples of the inorganic compound include potassium hydroxide, sodium hydroxide, lithium hydroxide, potassium carbonate, sodium carbonate, lithium carbonate and the like. Examples of the organic compound include CH ₃ ONa, C ₂ H ₅ ONa, CH ₃ OLi, C ₂ H ₅ OLi, CH ₃ OK, C ₂ H ₅ OK and the like. The amount of the catalyst used is preferably 0.1 to 10 mmol equivalent with respect to 1 mol of the alkanediol.

The reaction step is carried out in a pressure reactor such as an autoclave with the temperature of the reaction system preferably set to 100 ° C. to 170 ° C., more preferably 130 ° C. to 150 ° C., while stirring the raw materials. Ethylene oxide or propylene oxide can be added while changing the order, ratio, etc. in order to obtain a diol compound having a desired structure.

In the first production method, a purification step can be provided after the reaction step, if necessary. This purification step can include conventionally known operations such as chromatographic separation and concentration, which are carried out in the synthesis of general organic compounds.

The cleaning agent composition of the present invention contains the above-mentioned diol compound of the present invention .
Further, as described above, the cleaning agent composition of the present invention also includes the following aspects.
A low-foaming detergent composition containing a compound represented by the following general formula (11), an anionic surfactant, and a chelating agent, wherein the anionic surfactant is a salt of alkylbenzene sulfonic acid. It is characterized by containing an alkyl ether sulfate of polyoxyethylene or polyoxyalkylene .
HO-R ^1- O-A ^1- H (11)
(In the formula, R ¹ is an alkylene group having 8 to 12 carbon atoms, A ¹ is a divalent group represented by − (R ⁵ O) _S −, and R ⁵ has 2 carbon atoms. or 3 alkylene group, s is an integer from 3 to 6, - ^(R 5 _{O) S} - in ^{R 5} is also all be identical or may be different).
The cleaning composition may contain other components, if desired. Other ingredients include anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, chelating agents, antioxidants, fragrances, antibacterial agents, fungicides, water, organic solvents. And so on. The content ratio of the total amount of the other components excluding water and the organic solvent is 100 parts by mass when the content of the diol compound (the diol compound of the present invention or the compound represented by the general formula (11)) is 100 parts by mass. From the viewpoint of cleanability against dirt adhering to the article, it is preferably 10 to 1600 parts by mass, and more preferably 100 to 700 parts by mass.

Examples of the anionic surfactant include linear alkylbenzene sulfonic acid or a salt thereof, α-olefin sulfonic acid salt, linear or branched alkyl sulfate ester salt, alkyl ether sulfate ester salt or alkenyl ether sulfate ester salt, and poly. Alkyl ether sulfate of oxyethylene or polyoxyalkylene, alkane sulfonate having an alkyl group, α-sulfo fatty acid ester salt, higher fatty acid salt, alkyl ether carboxylate, polyoxyalkylene ether carboxylate, alkylamide ether carboxylic Sulfate or alkenylamide ether carboxylate, carboxylic acid type such as acylaminocarboxylate, alkyl phosphate ester salt, polyoxyalkylene alkyl phosphate ester salt, polyoxyalkylene alkylphenyl phosphate ester salt, glycerin fatty acid ester monoline Examples thereof include phosphoric acid ester type anionic surfactants such as acid ester salts.

Examples of the cationic surfactant include dialkyldimethylammonium salt, alkyltrimethylammonium salt, alkyltriethylammonium salt, alkoxyalkyltrimethylammonium salt and the like.

Examples of the nonionic surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, sorbitan monostearate, polyoxyethylene alkyl amine and the like.

Amphoteric tensides include alkylbetaine, alkylamide betaine, alkylhydroxysulfobetaine, alkylamidehydroxysulfobetaine, alkylcarboxymethylhydroxyethyl imidazolinium betaine, alkylamide hydroxyethyl amino acid amphoteric tenside, alkyliminodiacetic acid. Examples include salt.

Chelating agents include citric acid, malic acid, tartaric acid, succinic acid, methylglycine diacetic acid, glutamate diacetic acid, hydroxyethyliminodiacetic acid, ethylenediaminediaminediaminecetic acid, nitrilotriacetic acid, 1,3-propanediaminetriacetic acid, 1 , 3-Diamino-2-hydroxypropanetetraacetic acid, glycol etherdiaminetetraacetic acid, ethylenediaminetetraacetic acid, diethylenetriaminetetraacetic acid, triethylenetetraaminehexacetic acid, dihydroxyethylglycine, and polycarboxylic acids such as hydroxyethylethylenediaminedicarboxymethylglutamic acid. Alternatively, a salt thereof, tripoliphosphoric acid or a salt thereof, etc. may be mentioned.

The organic solvent is not particularly limited as long as it is miscible with water. For example, alcohols such as ethanol, 1-propanol, 2-propanol and 1-butanol; glycols such as propylene glycol, butylene glycol and hexylene glycol; polyglycols such as diethylene glycol, triethylene glycol and tetraethylene glycol; diethylene glycol monomethyl ether, Examples thereof include alkyl ethers such as diethylene glycol dimethyl ether.

Further, the cleaning agent composition of the present invention preferably contains the diol compound of the present invention, an anionic surfactant, and a chelating agent.
In addition, the cleaning agent composition of the present invention also includes the following aspects.
A low-foaming detergent composition containing a compound represented by the following general formula (11), an anionic surfactant, and a chelating agent, wherein the anionic surfactant is a salt of alkylbenzene sulfonic acid. , And a cleaning agent composition containing an alkyl ether sulfate of polyoxyethylene or polyoxyalkylene .
HO-R ^1- O-A ^1- H (11)
(In the formula, R ¹ is an alkylene group having 8 to 12 carbon atoms, A ¹ is a divalent group represented by − (R ⁵ O) _S −, and R ⁵ has 2 carbon atoms. or 3 alkylene group, s is an integer from 3 to 6, - ^(R 5 _{O) S} - in ^{R 5} is also all be identical or may be different).
The content ratio of the anionic surfactant and the chelating agent is preferably 3 when the content of the diol compound (the diol compound of the present invention or the compound represented by the general formula (11)) is 100 parts by mass. ~ 400 parts by mass and 3 to 200 parts by mass, more preferably 5 to 150 parts by mass and 5 to 100 parts by mass.

Further, the cleaning agent composition of the present invention is preferably a liquid substance containing a liquid medium such as water or an organic solvent. In this case, the lower limit of the content ratio of the diol compound is preferably 5% by mass, more preferably 10% by mass. The upper limit is usually 30% by mass.

The cleaning agent composition of the present invention is used for removing stains adhering to an article, that is, for cleaning, but this composition may be used as it is, or a diluted product diluted with water may be used. Good. When the diluted product is used for cleaning, the lower limit of the content ratio of the diol compound in the diluted product is preferably 0.1% by mass, more preferably 0.5% by mass from the viewpoint of detergency.

The cleaning agent composition of the present invention is suitable for washing dishes, clothes, etc. in combination with a dishwasher, a washing machine, and the like. It is also suitable for cleaning the cleaning tanks of these devices and the dirt adhering to the inner wall surface of the immersion tank for treating articles with a special liquid.

The cleaning method using the cleaning agent composition of the present invention is not particularly limited, and can be appropriately selected depending on the state of contamination of the article. An example of a general cleaning method is, at least, a method in which the composition is brought into contact with a contaminated portion and dirt is removed using a cleaning tool such as a brush. Since the cleaning agent composition of the present invention contains a diol compound having excellent low foaming properties, it is possible to reduce the amount of water used when rinsing with water after removing stains.

Hereinafter, the present invention will be specifically described with reference to Examples. In the following description, "part" is based on mass unless otherwise specified.

1. 1. Synthesis of diol compound Synthesis Example 1 (Synthesis of compound X-1)
160.3 g (1 mol) of 2-butyl-2-ethyl-1,3-propanediol was charged into an autoclave, 0.3 g of potassium hydroxide powder (6 mmol equivalent to the raw material) was added as a catalyst, and then the autoclave was added. The inside was sufficiently replaced with nitrogen gas. Then, while stirring these, while maintaining the temperature of the reaction system at 130 ° C. to 150 ° C., 176 g (4 mol) of ethylene oxide was press-fitted to start the addition polymerization reaction. Then, it was aged at the same temperature for 1 hour to complete the addition polymerization reaction. Then, the catalyst of the reaction system was neutralized with phosphoric acid, and then the reaction product was separated and recovered by liquid chromatography. When the obtained reaction product was subjected to LC-MS analysis under the following conditions, it was found to be a compound represented by the following formula (3) (see FIG. 1). Hereinafter, this compound is shown as X-1 (see Table 1).
ESI-MS: m / z = 337 (M + H) ⁺

(LC-MS analysis conditions)
Measuring equipment: LC / Ultimate 3000 (manufactured by Thermo Fisher Scientific)
: MS / maXis (manufactured by Bruker)
Column used for LC: ACQUITY UPLC BEH C18 1.7um 2.1mm x 150mm (manufactured by Waters)
Ionization method: ESI (possive)
Ion source temperature: 200 ° C
MS detector: TOF
Measurement range: 70 m / z to 1550 m / z

Synthesis example 2
Compound X-2 was obtained in the same manner as in Synthesis Example 1 except that 4 mol of propylene oxide was used instead of 4 mol of ethylene oxide (see Table 1).

Synthesis example 3
Compound X-3 was obtained in the same manner as in Synthesis Example 1 except that a mixture of 2 mol of ethylene oxide and 2 mol of propylene oxide was used instead of 4 mol of ethylene oxide (see Table 1).

Synthesis example 4
Instead of the addition polymerization reaction in which ethylene oxide (4 mol) is press-fitted and aged at the same temperature for 1 hour, 2 mol of ethylene oxide is press-fitted at 130 ° C. to 150 ° C. and aged at the same temperature for 1 hour. , 2 mol of propylene oxide was press-fitted at 130 ° C. to 150 ° C. and aged at the same temperature for 1 hour to complete the addition polymerization reaction. After completion of the reaction, the same operation as in Synthesis Example 1 was carried out to obtain compound X-4 (see Table 1).

Synthesis example 5
2,4-Diethyl-1,5-pentanediol was used instead of 2-butyl-2-ethyl-1,3-propanediol, except that the amount of ethylene oxide used was changed from 4 mol to 3 mol. The same operation as in Synthesis Example 1 was carried out to obtain Compound X-5 (see Table 1).

Synthesis example 6
Synthesis example except that 2-methyl-1,8-octanediol was used instead of 2-butyl-2-ethyl-1,3-propanediol and the amount of ethylene oxide used was changed from 4 mol to 5 mol. The same operation as in No. 1 was carried out to obtain compound X-6 (see Table 1).

Synthesis example 7
The same as in Synthesis Example 1 except that 1,12-dodecanediol was used instead of 2-butyl-2-ethyl-1,3-propanediol and the amount of ethylene oxide used was changed from 4 mol to 6 mol. The operation was carried out to obtain compound X-7 (see Table 1).

Synthesis example 8
The same as in Synthesis Example 1 except that 1,6-hexanediol was used instead of 2-butyl-2-ethyl-1,3-propanediol and the amount of ethylene oxide used was changed from 4 mol to 6 mol. The operation was carried out to obtain compound X-8 (see Table 1).

Synthesis example 9
Compound X-9 was obtained in the same manner as in Synthesis Example 1 except that 1,14-tetradecanediol was used instead of 2-butyl-2-ethyl-1,3-propanediol (Table 1). reference).

Synthesis example 10
Compound Y-1 was obtained in the same manner as in Synthesis Example 1 except that the amount of ethylene oxide used was changed from 4 mol to 12 mol (see Table 1).

Synthesis example 11
Compound Y-2 was obtained in the same manner as in Synthesis Example 1 except that the amount of ethylene oxide used was changed from 4 mol to 16 mol (see Table 1).

For the evaluation experiment described later, the compounds obtained in Synthesis Examples 12 and 13 were used as conventionally known surfactants.

Synthesis example 12
Lauryl alcohol was used instead of 2-butyl-2-ethyl-1,3-propanediol, and the same operation as in Synthesis Example 1 was carried out except that the amount of ethylene oxide used was changed from 4 mol to 5 mol. Compound Z-1 represented by the following formula was obtained.
C ₁₂ H _25- O- (CH _2- CH _2- O) _5- H

Synthesis example 13
Except that lauryl alcohol and tridecyl alcohol were used instead of 2-butyl-2-ethyl-1,3-propanediol, and a mixture of 6 mol of ethylene oxide and 1 mol of propylene oxide was used instead of 4 mol of ethylene oxide. The same procedure as in Synthesis Example 1 was carried out to obtain a mixture Z-2 composed of a plurality of types of polyoxyethylene polyoxyalkylene alkyl ethers.

2. 2. Measurements Experiment example of a dynamic surface tension 1-1 to 1-9 and Comparative Examples 1-1 to 1-4
In order to measure the dynamic surface tension of the diol compounds and the like obtained in Synthesis Examples 1 to 13, an aqueous solution containing each compound at a concentration of 0.1% by mass was prepared, and a foam pressure method manufactured by Chem-Dyne Research Corporation was prepared. Using a dynamic surface tension meter "SENSA DYNE" (trade name), the dynamic surface tension of 1, 3, 5 bubbles / sec was measured at 20 ° C. The measurement probe diameter is 0.5 mm. It is assumed that the 1 bubble / sec aqueous solution is in the static region where the surface tension has almost reached equilibrium, and the 5 bubble / sec aqueous solution is in the dynamic region, and the dynamic surface of 5 bubbles / sec. The difference (ΔT) between the tension and the dynamic surface tension of 1 bubble / sec was determined. The results are shown in Table 2.

In general, in an aqueous solution of a surfactant, ΔT tends to decrease when a large amount of the surfactant is present at the interface between water and the atmosphere. Table aqueous solution of Compound X-1 to X-9 in Experimental Example 1-1 to 1-9 of 3, since ΔT is 2.0 or less, after the good foam breakage which was bubbled These aqueous solutions It is presumed to be.

3. 3. Production and Evaluation experiment examples of detergent compositions 2-1 to 2-11 and Comparative Examples 2-1 to 2-4
The compounds X-1 to X-9, Y-1, Y-2, Z-1 and Z-2 shown in Table 2 are mixed with sodium alkylbenzene sulfonate having 12 carbon atoms in the alkyl group (hereinafter, simply "alkylbenzene". "Sodium sulfonate"), polyoxyethylene (3) sodium lauryl ether sulfate (hereinafter simply referred to as "sodium polyoxyethylene lauryl ether sulfate"), ethylenediamine tetrasodium acetate, citric acid and water, as shown in Table 3. The mixture was mixed in proportion to produce a cleaning agent composition.
Next, the foaming property, rinsing property and detergency were evaluated by the methods shown below. The results are also shown in Table 3.

(1) Foaming property Each cleaning agent composition was diluted 100-fold with ion-exchanged water. Then, 50 mL of the diluted solution was weighed into a measuring cylinder with a stopper having a volume of 200 mL and sealed. Then, it was tilted 10 times at 1 time / sec and shaken to foam. Immediately after that, the measuring cylinder was allowed to stand and the volume (mL) of foam was measured. In addition, the volume (mL) of the foam was measured even after 1 minute had passed. From these measured values, the foaming property was determined according to the following criteria.

<Criteria for foaming property>
(Immediately after foaming)
⊚: Foam volume was less than 20 mL 〇: Foam volume was 20 mL or more and less than 50 mL Δ: Foam volume was 50 mL or more and less than 100 mL ×: Foam volume was 100 mL or more (foaming) 1 minute later)
⊚: Foam volume was less than 20 mL 〇: Foam volume was 20 mL or more and less than 50 mL Δ: Foam volume was 50 mL or more and less than 100 mL ×: Foam volume was 100 mL or more

(2) Rinseability and detergency A stain substance formed by mixing 800 parts, 200 parts, and 0.1 parts of Japanese lard oil, Japanese sesame oil, and red dye in all five ceramic dishes with a diameter of 25 cm, respectively. 3 g was applied and left for 12 hours under the conditions of 20 ° C. to 30 ° C. Next, the dirty dishes were brush-washed for 1 minute in a cleaning solution cleaning solution (temperature: 40 ° C., usage amount: 3.5 L) in which the cleaning agent composition shown in Table 3 was diluted 100-fold with water. Then, the surface of all five dishes was rinsed with water at 30 ° C. until the bubbles disappeared, and the rinse property was evaluated by the total amount of water used until the bubbles disappeared completely. Then, after draining, it was visually observed whether or not a dirty substance remained on the surface of the dish, and the detergency was evaluated.

<Criteria for rinsing>
⊚: Total amount of water used was 1000 mL or less 〇: Total amount of water used was 1500-2000 mL Δ: Total amount of water used was 2500-4000 mL ×: Water used The total amount was 4500 mL or more

<Criteria for cleaning>
◯: No stains remained on all 5 dishes, and there was no discomfort such as sliminess when touching the surface of the dishes. Δ: Dirt was observed on some dishes, or stains were found. No residue was observed, but there was a slight sense of discomfort such as sliminess when touched by hand. ×: Dirt remained on all 5 dishes.

According to Table 3, experimental examples 2-1 to 2-11 of the detergent composition using the X-1 to X-9 is a diol compound of the present invention, low foaming, rinsability and detergency Was excellent. On the other hand, Comparative Examples 2-1 and 2-2 of the cleaning agent composition using the diol compound Y-1 or Y-2 not included in the present invention do not have sufficient low foaming property and wash the dishes. It was not economical, as it required a large amount of water for rinsing after cleaning.

By using the cleaning agent composition of the present invention, dirt adhering to the article can be efficiently removed. In addition, since it contains a diol compound having excellent low foaming properties, the amount of water used during rinsing can be reduced, which is economical.

Claims (4)

A compound characterized by being represented by the following general formula (1).
HO-R ^1- O-A ^1- H (1)
(In the formula, R ¹ is a branched alkylene group selected from any of the following formulas (5) to (7) , and A ¹ is a divalent group represented by − (R ⁵ O) _S −. in and, ^{R 5} is an alkylene group having 2 or 3 carbon atoms, s is an integer of ^{3 ~ 6, - (R 5} O) S - be all ^{R 5} are the same in, or different May be.)
A low-foaming cleaning agent composition containing the compound according to claim 1. The low-foaming cleaning composition according to claim 2, further comprising an anionic surfactant and a chelating agent. A low-foaming detergent composition containing a compound represented by the following general formula (11), an anionic surfactant, and a chelating agent, wherein the anionic surfactant is a salt of alkylbenzene sulfonic acid. A low-foaming detergent composition comprising, and an alkyl ether sulfate of polyoxyethylene or polyoxyalkylene .
HO-R ^1- O-A ^1- H (11)
(In the formula, R ¹ is an alkylene group having 8 to 12 carbon atoms, A ¹ is a divalent group represented by − (R ⁵ O) _S −, and R ⁵ has 2 carbon atoms. or 3 alkylene group, s is an integer from 3 to 6, - ^(R 5 _{O) S} - in ^{R 5} is also all be identical or may be different).