JP2004131678A - Chemically decomposable surfactant and detergent - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To solve problems such that since an aqueous detergent or various emulsifiers containing a surfactant for the use of cleaning mechanical parts in an industrial field or minute cleaning of electronic materials are an aqueous emulsion containing oil, water and the surfactant even after the use, economical burdens for waste water treatment and destroying the emulsion are large and also there is a fear of the deterioration of product performance caused by residual surfactant, etc., in the product. <P>SOLUTION: This chemically decomposable surfactant having 1, 3-dioxolane ring and losing its surfactant function after the use to enable the easy separation of oils and water as a useful function that conventional surfactants do not have, and the detergent and emulsifier blended with the surfactant are provided. <P>COPYRIGHT: (C)2004,JPO

Description

（式中、Ｒ_１およびＲ_２は水素原子、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基、ウンデシル基、ドデシル基、トリデシル基、テトラデシル基、ペンタデシル基、ヘキサデシル基、ヘプタデシル基、オクタデシル基などで、炭素数１〜２２のアルキル基あるいはアルケニル基である。エチレンオキシドの付加モル数を表わすｎとしては、１から２０のものであり、Ｍはアルカリ金属または−ＮＨ_４基、アミン類である。）
で表わされる１，３−ジオキソラン環を分子内に有するポリオキシエチレンアルキルエーテル硫酸塩としての界面活性剤と、一般式（ＩＩ）：
【化４】

（式中、Ｒ_１、Ｒ_２およびＭは一般式（Ｉ）のＲ_１、Ｒ_２およびＭと同じであり、Ｒ_３は水素原子またはメチル基である）
で表わされる１，３−ジオキソラン環を分子内に有するアルキルアミノスルホン酸塩としての界面活性剤である。
また、これらの界面活性剤の製造方法としては、次のような方法が例として挙げられる。
すなわち、ケトンあるいはアルデヒドとグリセリンを、酸触媒の存在下に反応させることにより、長鎖アルキル基を有する４−ヒドロキシメチル−１，３−ジオキソラン化合物が得られる。その後、得られたジオキソラン化合物をエチレンオキシドやオリゴエチレングリコール類によるエトキシ化後、硫酸化と中和によって硫酸塩型の界面活性剤（Ｉ）を得る。また、４−ヒドロキシメチル−１，３−ジオキソラン化合物をエピクロルヒドリン，エピブロモヒドリンなどのエポキシ化合物によるグリシジルエーテル化後、タウリン、メチルタウリンなどのアミノエタンスルホン酸塩と反応させることでスルホン塩型の目的とする界面活性剤（ＩＩ）を製造することができる。
【０００８】
【発明の実施の形態】本発明のアニオン界面活性剤は１，３−ジオキソラン環を有する化合物由来の構成単位と、アルキルエーテル硫酸塩あるいはアルカンスルホン酸塩由来の構成単位からなる化合物である。
【０００９】本発明において「アルキルエーテル硫酸塩」とは、アルキル基にポリオキシエチレン、オリゴエチレングリコールが付加した化合物の硫酸塩を意味し、「アルカンスルホン酸塩」とは、アルキル基にアミノエタンスルホン酸塩が付加した化合物を意味する。
【００１０】一般式（Ｉ）および一般式（ＩＩ）における「Ｍ」のアルカリ金属としては、ナトリウム金属、カリウム金属などが、またアミンとしてはアンモニウム基、エタノールアミン類が挙げられる。
【００１１】本発明の洗浄剤、乳化剤の有効成分となるアニオン界面活性剤は、一般式（Ｉ）の化合物、一般式（ＩＩ）の化合物を０．０１〜５０重量％の割合で含むのが好ましい。これらのアニオン界面活性剤は単独で、あるいは適宜組み合わせて用いることができる。
【００１２】本発明においては、このアニオン界面活性剤は１種で用いてもよいし、２種以上を組み合わせてもよく、性能向上のためのビルダー成分や有機溶剤を組み合わせてもよい。
【００１３】
【実施例】
この発明を実施例により以下説明するが、この発明はこれらの実施例により限定されるものではない。
【００１４】
［合成例１］
【化５】

２−メチル−２−トリデシル−４−ヒドロキシメチル−１，３−ジオキソランエーテル硫酸塩は次のとおりに合成した。
２−ペンタデカノン５６．６ｇ、グリセリン２８．０ｇ、ｐ−トルエンスルホン酸０．５ｇ、トルエン１００ｍＬの混合物を、水が留出してこなくなるまで加熱還流した。反応終了後、冷却して５％炭酸ナトリウム水溶液で１回、水で３回洗浄し、トルエンを留去した後、減圧蒸留して２−メチル−２−トリデシル−４−ヒドロキシメチル−１，３−ジオキソラン６０．５ｇ（収率８０％）を得た。この２−メチル−２−トリデシル−４−ヒドロキシメチル−１，３−ジオキソラン１５．０ｇ、ｔｅｒｔ−ブトキシカリウム６．０ｇ、ジエチレングリコールモノクロライド６．５ｇ、ｔｅｒｔ−ブタノール２０ｍＬを６０℃で４８時間反応させ、析出塩を濾過した後、減圧蒸留してジエチレングリコール２−メチル−２−トリデシル−４−ヒドロキシメチル−１，３−ジオキソランエーテル８．５ｇ（収率４４％）を得た。得られた１，３−ジオキソラン化合物８．０ｇ、スルファミン酸２．０ｇ、ＤＭＦ２０ｍＬを、反応温度を５０℃に保持して６時間反応を続行した。反応終了後、室温まで温度を下げ、水酸化ナトリウム２．０ｇをメタノール２０ｍＬに溶解して加え、溶媒を留去した後、これにエタール：２−プロパノール（１：１）３０ｍＬを加えて、析出塩を濾過した後に溶媒を除去し、２−メチル−２−トリデシル−４−ヒドロキシメチル−１，３−ジオキソランエーテル硫酸ナトリウム８．０ｇ（収率８７％）を得た。この化合物の^１Ｈ　ＮＭＲ（Ｄ_２Ｏ）の分析結果は、δ０．８８（ｔ，Ｊ＝６Ｈｚ，ＣＨ_３，３Ｈ），１．００−２．００（ｍ，ＣＨ_２，ＣＨ_３Ｃ−Ｏ，２７Ｈ），３．５０−４．４０（ｍ，ＯＣＨ_２ＣＨ（ＣＨ_２Ｏ）Ｏ，ＯＣＨ_２ＣＨ_２Ｏ，ＣＨ_２ＯＳ，１１Ｈ）で、ＩＲ（ＫＢｒ）の分析結果は、３３３０，２９２０，１１１０，１０５０　ｃｍ^−１．であった。
【００１５】
［合成例２］
【化６】

２−メチル−２−ウンデシル−４−ヒドロキシメチル−１，３−ジオキソランアミノスルホン酸塩は次のとおりに合成した。
２−トリデカノン１００．０ｇ、グリセリン５６．０ｇ、ｐ−トルエンスルホン酸１．０ｇ、トルエン２００ｍＬの混合物を、水が留出してこなくなるまで加熱還流した。反応終了後、冷却して５％炭酸ナトリウム水溶液で１回、水で３回洗浄し、トルエンを留去した後、減圧蒸留して２−メチル−２−ウンデシル−４−ヒドロキシメチル−１，３−ジオキソラン１１８．２ｇ（収率８６％）を得た。この２−メチル−２−ウンデシル−４−ヒドロキシメチル−１，３−ジオキソラン１３．６ｇ、エピクロロヒドリン４．６ｇ、水酸化ナトリウム水溶液（４０％）５ｍＬ、テトラブチルアンモニウムブロミド０．５ｇ、ヘキサン２０ｍＬを３０℃で６時間反応させ、析出塩を濾過した後、減圧蒸留してグリシジル２−メチル−２−ウンデシル−４−ヒドロキシメチル−１，３−ジオキソランエーテル１４．０ｇ（収率８５％）を得た。得られた１，３−ジオキソラン化合物６．６ｇ、メチルタウリンナトリウム水溶液（約６０％）５．４ｇを、反応温度を６０℃に保持して１時間反応させた。反応終了後、室温まで温度を下げ、これにエタール：２−プロパノール（１：１）３０ｍＬを加えて、析出塩を濾過した後に溶媒を除去し、２−メチル−２−ウンデシル−４−ヒドロキシメチル−１，３−ジオキソランアミノスルホン酸ナトリウム．８．５ｇ（収率８７％）を得た。この化合物の^１Ｈ　ＮＭＲ（Ｄ_２Ｏ）の分析結果は、δ０．８８（ｔ，Ｊ＝６Ｈｚ，ＣＨ_３，３Ｈ），１．００−２．００（ｍ，ＣＨ_２，ＣＨ_３Ｃ−Ｏ，２３Ｈ），２．３０−３．２０（ｍ，ＣＨＣＨ_２Ｎ（ＣＨ_３）ＣＨ_２ＣＨ_２Ｓ，１０Ｈ），３．５０−４．４０（ｍ，ＯＣＨ_２ＣＨ（ＣＨ_２Ｏ）ＯＣＨ_２，５Ｈ）で、ＩＲ（ＫＢｒ）の分析結果は、３３３０，２９２０，１１１０，１０５０　ｃｍ^−１．であった。
【００１６】
［界面活性剤］
合成例１と同様の手順により、表１に示す化学分解性界面活性剤を合成し、後述の表３、４のように用いた。
【００１７】
【表１】

【００１８】
合成例２と同様の手順により、表２に示す化学分解性界面活性剤を合成し、後述の表３、４のように用いた。
【００１９】
【表２】

【００２０】
［酸分解性の測定例］
合成した界面活性剤の分解性の評価は、塩酸水溶液中で撹拌した時に生成するケトンあるいはアルデヒドをヘキサンで抽出し、その量を定量することにより行った。
栓付の三角フラスコに界面活性剤１％溶液２５ｍＬを、所定の塩酸濃度になるように調製し、２５℃で攪拌して、分解反応終了後に分液ロートに注ぎ、ヘキサン２５ｍＬを加えて抽出操作を２回行った。得られたヘキサン溶液を合わせて、ヘキサンをロータリーエバポレーターで留去して残ったケトンの重量から分解率を測定した。結果を表３に示す。
【００２１】
【表３】

【００２２】
［洗浄力試験実施］
洗浄モデル板としてガラス板（スライドガラス）を用いて、牛脂と大豆油を体積比１：１で混合した油脂２０ｇ、モノオレイン０．２５ｇ、オイルレッド０．１ｇをクロロホルム６０ｍＬに溶かし、２５℃に保ったこの汚れにガラス板を浸した。汚れを付着したモデル汚れガラス板は、２５℃で風乾し、風乾放置時間１時間以上２時間以内に洗浄を行った。洗浄は、ＪＩＳ　Ｋ３３７０に準拠したリーナッツ改良洗浄力試験器による洗浄操作を３０℃で行った後、洗浄したモデル汚れガラス板は６枚１組として、クロロホルムで残った汚れを抽出して５０ｍＬのクロロホルム溶液とし、このクロロホルム溶液の５１０ｎｍにおける透過率（％）を分光光度計で測定し、未洗浄のモデル汚れガラス板から作ったクロロホルム溶液との透過率（％）の差を下記の式により計算して洗浄力評価を行った。ＪＩＳ指標洗剤としては、ドデシルベンゼンスルホン酸ナトリウム、エタノール、尿素および水を質量比１５：５：５：７５で混合処方した洗剤を用いた。結果を表４に示す。
洗浄率（％）＝（洗浄後透過率−未洗浄透過率）／（１００−未洗浄透過率）×１００
【００２３】
【表４】

【００２４】
【発明の効果】
本発明による界面活性剤は、０．５ｍｏｌ／Ｌ（約０．２％）以下の塩酸水溶液中でも１時間以内に、極めて容易に分解する。このため、洗浄後の油水分離が容易になり、洗浄排水から油溶性の汚れの取り出しが簡便となり、廃水処理にかかる負担が低減できる。また、その洗浄力評価を行った結果もＪＩＳに定める指標洗剤と同等以上であり、既存の界面活性剤に替えて成分処方を行った場合も、同等以上の洗浄力を示すものである。このため、従来の洗浄剤に比べ廃水処理の容易な洗浄剤とすることができる。[0001]
BACKGROUND OF THE INVENTION The present invention relates to a water-soluble detergent and an emulsifier containing a surfactant for various uses, which are chemically decomposable surfactants which can easily separate oil and water by losing their surfactant function after use. And a detergent and an emulsifier containing the same.
[0002]
2. Description of the Related Art In the industrial field, cleaning applications such as cleaning of various mechanical parts and plastics, precision cleaning of electronic materials such as printed circuit boards and semiconductors, and other water-based emulsions such as emulsion polymerization and water-based paints are required. In the field, detergents and emulsifiers containing surfactants are used. However, there are problems such as a large economic burden for wastewater treatment and emulsion destruction after use, and deterioration of product performance. In view of this, nonionic, carboxylate and quaternary ammonium salt types in which a surfactant has degradability have been proposed, but their performance is not sufficient. (For example, Non-Patent Documents 1 and 2) Application to polymer emulsions has also been proposed, but synthesis of the activator often requires a special chemical. (For example, Patent Document 1)
[0003]
2. Description of the Related Art Problems after using conventional detergents and emulsifiers are an emulsion state of an oil-soluble substance and a water-soluble substance, so that oil treatment and water treatment cannot be performed separately. A large burden is required for emulsion destruction. In addition, in the case of environmental pollution due to discharge of oil stains and the like which have become water-soluble with a water-based cleaning agent containing a surfactant or a water-based paint containing a surfactant, the water resistance of the coating film is reduced by the remaining surfactant. A drop occurs. Furthermore, in the synthesis of polymers or chemical products by emulsion polymerization or micelle reaction, there is a problem of lowering of purity and lowering of performance due to residual impurities such as surfactants in the product. For this reason, development of surfactants, detergents, and emulsifiers excellent in environmental adaptability that can easily destroy emulsions has become an important issue.
[0004]
[Patent Document 1]
JP-A-3-281602 [Non-Patent Document 1]
L. Waclas, B .; Burczyk, Tenside Detergents, 1981, Volume 18, p19-22
[Non-patent document 2]
Shingo Yamamura et al., Journal of American Oil Chemistry Society, 1989, 66, p1165-1170.
[0005]
The use of the detergent or emulsifier of the present invention causes the surfactant to lose its function, thereby facilitating the destruction of the emulsion state and oil / water separation, and efficiently separating oil stains in wastewater. To reduce the burden on wastewater treatment, improve the water resistance of coating films made from water-based paints containing surfactants, and to retain impurities such as surfactants in products manufactured by emulsion polymerization or micelle reaction. The purpose of the present invention is to reduce the deterioration of product performance due to the above.
[0006]
In response to this demand, the present inventors have developed a chemically degradable surfactant having a 1,3-dioxolane ring utilizing the reaction of an aldehyde or ketone with an epoxy compound or a polyol compound. Develops an anionic surfactant based on a chemical agent, and as a useful function not found in conventional surfactants, a composite function with excellent environmental compatibility that facilitates oil-water separation by losing the surfactant function after use We have completed a surface active agent and a detergent and emulsifier containing it.
The newly developed chemically decomposable surfactant has the characteristic that the balance between hydrophilicity and lipophilicity can be adjusted by adjusting the alkyl chain length and the oxyethylene chain length. We can provide the best ones.
That is, the present invention provides a compound represented by the general formula (I):
Embedded image

(Wherein, R ₁ and R ₂ are hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl) Group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, etc., and is an alkyl group or an alkenyl group having 1 to 22 carbon atoms. And M is an alkali metal or —NH ₄ group, amines.)
A surfactant as a polyoxyethylene alkyl ether sulfate having a 1,3-dioxolane ring in the molecule represented by the following general formula (II):
Embedded image

_(Wherein, R 1, _{R 2} and M are the same as _R 1, _{R 2} and M in the general formula (I), _{R 3} is a hydrogen atom or a methyl group)
Is a surfactant as an alkylaminosulfonic acid salt having a 1,3-dioxolane ring in the molecule.
In addition, examples of a method for producing these surfactants include the following methods.
That is, a ketone or aldehyde is reacted with glycerin in the presence of an acid catalyst to obtain a 4-hydroxymethyl-1,3-dioxolane compound having a long-chain alkyl group. Thereafter, the obtained dioxolane compound is ethoxylated with ethylene oxide or oligoethylene glycols, and then sulfated and neutralized to obtain a sulfate type surfactant (I). Further, a 4-hydroxymethyl-1,3-dioxolane compound is glycidyl-etherified with an epoxy compound such as epichlorohydrin or epibromohydrin, and then reacted with an aminoethanesulfonic acid salt such as taurine or methyltaurine to form a sulfone salt type. The desired surfactant (II) can be produced.
[0008]
BEST MODE FOR CARRYING OUT THE INVENTION The anionic surfactant of the present invention is a compound comprising a structural unit derived from a compound having a 1,3-dioxolane ring and a structural unit derived from an alkyl ether sulfate or an alkane sulfonate.
In the present invention, "alkyl ether sulfate" means a sulfate of a compound in which polyoxyethylene and oligoethylene glycol are added to an alkyl group, and "alkane sulfonate" means aminoethane sulfate. It means a compound to which a sulfonate is added.
In the general formulas (I) and (II), examples of the alkali metal of "M" include sodium metal and potassium metal, and examples of the amine include an ammonium group and ethanolamines.
The anionic surfactant which is an active ingredient of the detergent and emulsifier of the present invention contains the compound of the general formula (I) and the compound of the general formula (II) at a ratio of 0.01 to 50% by weight. preferable. These anionic surfactants can be used alone or in appropriate combination.
In the present invention, the anionic surfactant may be used alone or in combination of two or more, and may be combined with a builder component or an organic solvent for improving the performance.
[0013]
【Example】
The present invention will be described below with reference to examples, but the present invention is not limited to these examples.
[0014]
[Synthesis Example 1]
Embedded image

2-Methyl-2-tridecyl-4-hydroxymethyl-1,3-dioxolane ether sulfate was synthesized as follows.
A mixture of 56.6 g of 2-pentadecanone, 28.0 g of glycerin, 0.5 g of p-toluenesulfonic acid and 100 mL of toluene was heated to reflux until no more water distilled out. After completion of the reaction, the mixture was cooled and washed once with a 5% aqueous sodium carbonate solution and three times with water. After distilling off toluene, the residue was distilled under reduced pressure to give 2-methyl-2-tridecyl-4-hydroxymethyl-1,3. -Dioxolane 60.5 g (80% yield) was obtained. 15.0 g of this 2-methyl-2-tridecyl-4-hydroxymethyl-1,3-dioxolane, 6.0 g of potassium tert-butoxy, 6.5 g of diethylene glycol monochloride, and 20 mL of tert-butanol were reacted at 60 ° C. for 48 hours. After filtration of the precipitated salt, the residue was distilled under reduced pressure to obtain 8.5 g of diethylene glycol 2-methyl-2-tridecyl-4-hydroxymethyl-1,3-dioxolane ether (44% yield). 8.0 g of the obtained 1,3-dioxolane compound, 2.0 g of sulfamic acid, and 20 mL of DMF were reacted for 6 hours while maintaining the reaction temperature at 50 ° C. After completion of the reaction, the temperature was lowered to room temperature, 2.0 g of sodium hydroxide was dissolved in 20 mL of methanol and added. After the solvent was distilled off, 30 mL of etal: 2-propanol (1: 1) was added thereto, and the mixture was precipitated. After the salt was filtered, the solvent was removed to obtain 8.0 g of sodium 2-methyl-2-tridecyl-4-hydroxymethyl-1,3-dioxolane ether sulfate (87% yield). The result of ¹ H NMR (D ₂ O) analysis of this compound was δ 0.88 (t, J = 6 Hz, CH ₃ , 3H), 1.00-2.00 (m, CH ₂ , CH ₃ C—O). , _27H), at _{3.50-4.40 (m, OCH 2 CH (} CH 2 O) O, OCH 2 CH 2 O, CH 2 OS, 11H), analysis of the IR (KBr) are 3330,2920 , 1110, 1050 cm ^-1 . Met.
[0015]
[Synthesis Example 2]
Embedded image

2-Methyl-2-undecyl-4-hydroxymethyl-1,3-dioxolaneaminosulfonate was synthesized as follows.
A mixture of 100.0 g of 2-tridecanone, 56.0 g of glycerin, 1.0 g of p-toluenesulfonic acid, and 200 mL of toluene was heated to reflux until no more water distilled out. After completion of the reaction, the reaction mixture was cooled and washed once with a 5% aqueous sodium carbonate solution and three times with water. After distilling off toluene, the residue was distilled under reduced pressure to give 2-methyl-2-undecyl-4-hydroxymethyl-1,3. -Dioxolane 118.2 g (86% yield) was obtained. This 2-methyl-2-undecyl-4-hydroxymethyl-1,3-dioxolane 13.6 g, epichlorohydrin 4.6 g, sodium hydroxide aqueous solution (40%) 5 mL, tetrabutylammonium bromide 0.5 g, hexane After reacting 20 mL at 30 ° C. for 6 hours, the precipitated salt was filtered and then distilled under reduced pressure to obtain 14.0 g of glycidyl 2-methyl-2-undecyl-4-hydroxymethyl-1,3-dioxolane ether (yield: 85%). Got. 6.6 g of the obtained 1,3-dioxolane compound and 5.4 g of a sodium methyltaurine aqueous solution (about 60%) were reacted for 1 hour while maintaining the reaction temperature at 60 ° C. After the completion of the reaction, the temperature was lowered to room temperature, 30 mL of ethanol: 2-propanol (1: 1) was added, and the solvent was removed after filtering the precipitated salt, and 2-methyl-2-undecyl-4-hydroxymethyl was added. Sodium-1,3-dioxolaneaminosulfonate. 8.5 g (87% yield) was obtained. The result of ¹ H NMR (D ₂ O) analysis of this compound was δ 0.88 (t, J = 6 Hz, CH ₃ , 3H), 1.00-2.00 (m, CH ₂ , CH ₃ C—O). _{, 23H), 2.30-3.20 (m,} CHCH 2 N (CH 3) CH 2 CH 2 S, 10H), 3.50-4.40 (m, OCH 2 CH (CH 2 O) OCH 2 , 5H), the IR (KBr) analysis results were 3330, 2920, 1110, 1050 cm ^-1 . Met.
[0016]
[Surfactant]
According to the same procedure as in Synthesis Example 1, the chemically degradable surfactants shown in Table 1 were synthesized and used as shown in Tables 3 and 4 described below.
[0017]
[Table 1]

[0018]
Chemical degradable surfactants shown in Table 2 were synthesized by the same procedure as in Synthesis Example 2, and used as shown in Tables 3 and 4 described below.
[0019]
[Table 2]

[0020]
[Example of acid decomposability measurement]
Evaluation of the decomposability of the synthesized surfactant was carried out by extracting the ketone or aldehyde generated when stirred in an aqueous hydrochloric acid solution with hexane and quantifying the amount.
In a conical flask with a stopper, 25 mL of a 1% solution of a surfactant is prepared so as to have a predetermined hydrochloric acid concentration, stirred at 25 ° C., poured into a separating funnel after completion of the decomposition reaction, and added with 25 mL of hexane to perform an extraction operation. Was performed twice. The obtained hexane solutions were combined, hexane was distilled off by a rotary evaporator, and the decomposition rate was measured from the weight of the remaining ketone. Table 3 shows the results.
[0021]
[Table 3]

[0022]
[Perform detergency test]
Using a glass plate (slide glass) as a washing model plate, dissolve 20 g of fat and oil, 0.25 g of monoolein, and 0.1 g of oil red in 60 mL of chloroform by mixing beef tallow and soybean oil at a volume ratio of 1: 1. The glass plate was immersed in the kept dirt. The stained model stained glass plate was air-dried at 25 ° C., and was washed for at least one hour and no more than two hours. Washing was performed at 30 ° C. by using a leanut-improved detergency tester in accordance with JIS K3370, and a set of six washed model stained glass plates was used. This chloroform solution was measured for transmittance (%) at 510 nm of the chloroform solution using a spectrophotometer, and the difference in transmittance (%) from the chloroform solution prepared from an unwashed model stained glass plate was calculated by the following equation. To evaluate the detergency. As the JIS indicator detergent, a detergent in which sodium dodecylbenzenesulfonate, ethanol, urea and water were mixed and formulated at a mass ratio of 15: 5: 5: 75 was used. Table 4 shows the results.
Washing rate (%) = (transmittance after washing−unwashed transmittance) / (100−unwashed transmittance) × 100
[0023]
[Table 4]

[0024]
【The invention's effect】
The surfactant according to the present invention is extremely easily decomposed within 1 hour even in an aqueous hydrochloric acid solution of 0.5 mol / L (about 0.2%) or less. For this reason, oil-water separation after washing is facilitated, removal of oil-soluble dirt from washing wastewater is simplified, and the burden on wastewater treatment can be reduced. In addition, the results of the evaluation of the detergency are equal to or higher than the index detergent specified in JIS, and the same or higher detergency is obtained even when the component formulation is performed in place of the existing surfactant. For this reason, it is possible to provide a cleaning agent that can easily treat wastewater as compared with a conventional cleaning agent.

Claims (5)

General formula (I):

(Wherein, R ₁ and R ₂ are hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl) Group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group and the like, and is an alkyl group or an alkenyl group having 1 to 22 carbon atoms. And M is an alkali metal or —NH ₄ group, amines.)
A surfactant as a polyoxyethylene alkyl ether sulfate having a 1,3-dioxolane ring in the molecule represented by the following formula: General formula (II):

_(Wherein, R 1, _{R 2} and M are the same as _R 1, _{R 2} and M in the general formula (I), _{R 3} is a hydrogen atom or a methyl group)
A surfactant as an alkylaminosulfonic acid salt having a 1,3-dioxolane ring in the molecule represented by the formula: Polyoxyethylene alkyl ether sulfate (I) or alkylamino sulfonate (II) having a 1,3-dioxolane ring in the molecule. A detergent and an emulsifier containing one or both of the surfactants represented by the general formulas (I) and (II) according to claim 1 and 2 at a ratio of 0.01 to 50% by weight. After using a detergent and an emulsifier containing the surfactant represented by the general formula (I) or (II) according to claim 1 or 2, an acid is added thereto to decompose and break the surfactant to break the surface. A post-treatment method characterized by eliminating the activator.