JP2006316265A - Additive for high concentration anionic surfactant - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an additive useful as an agent for fluidizing alkyl sulfate and/or alkyl ether sulfate compositions, and to provide an anionic surfactant composition which contains the additive and has such good flowability that the alkyl sulfate and/or alkyl ether sulfate may be contained in high concentrations. <P>SOLUTION: This additive for high concentration anionic surfactants, comprising a nitrogen-containing compound, is characterized in that the nitrogen-containing compound is at least one compound selected from the group consisting of amide alcohol compounds, amide amine type compounds, betaine type compounds, and imidazoline type compounds. The anionic surfactant composition contains the additive for high concentration anionic surfactants. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to an additive for high concentration anionic surfactant and an anionic surfactant composition containing the same.

  Alkyl ether sulfates obtained by sulfation of alkylene oxide adducts of higher alcohols (oxyalkylene alkyl ethers) are less irritating to the skin and are widely used as liquid detergents, for example, anionic surfactants for shampoos, pharmaceuticals and cosmetics. Has been.

  Alkyl ether sulfate is usually produced as a paste-like or liquid composition containing water, but the concentration of the active ingredient can be determined in consideration of handling properties, efficiency of production equipment, cost of product transportation, fluidity, etc. It is desirable to set the concentration as high as possible. The fluidity of the alkyl ether sulfate composition is affected by the chemical structure of the raw material higher alcohol, the number of repeating oxyalkylene units, the amount of unreacted oxyalkylene alkyl ether, the content of by-product alkylene ether glycol and inorganic salts, etc. Even at the same active ingredient concentration, the fluidity is significantly different. For example, it is also known that the fluidity may decrease as the extraction of the alkyl ether sulfate composition from a drum can becomes difficult. Therefore, if the fluidity of a composition containing a high concentration of the alkyl ether sulfate can be improved without reducing the concentration, the production efficiency is improved and the transportation cost is reduced, which is extremely advantageous industrially.

  As a means for improving the fluidity of the alkyl ether sulfate composition, for example, (1) a composition containing an alkyl ether sulfate and a salt of an alkylene ether glycol sulfate obtained from a polyalkylene ether glycol as a viscosity modifier (for example, Patent Document 1), (2) Polyethylene glycol having an average molecular weight of 300 to 6000 is added at a ratio of 0.1 to 25% by mass with respect to the sulfate during or after the neutralization step of the oxyalkylene alkyl ether sulfate. A low-viscosity surfactant (for example, Patent Document 2) obtained in the above manner is disclosed.

  However, in the composition of (1) and the low-viscosity surfactant of (2), although some improvement in fluidity can be seen, it is not fully satisfactory and an alkyl having higher fluidity. It has been desirable to develop ether sulphate compositions and fluidizing agents that can provide such alkyl ether sulphate compositions.

JP 56-36596 A JP 50-116383 A

  The present invention provides a novel additive useful as a fluidizing agent for high-concentration anionic surfactants such as alkyl sulfate and alkyl ether sulfate compositions, and a high-concentration anionic surfactant composition containing the additive.

  The present inventors show that nitrogen-containing compounds, particularly amide alcohol compounds, amidoamine type compounds, betaine type compounds, and imidazoline type compounds have an excellent fluidity improving effect on alkyl sulfate and alkyl ether sulfate compositions. I found.

（式中、Ｒ¹は炭素数５〜２３の水酸基を有していてもよい炭化水素基、好ましくは直鎖もしくは分岐鎖のアルキル基又はアルケニル基、Ｒ²は水素原子、あるいは炭素数１〜３のアルキル基、好ましくは直鎖もしくは分岐鎖のアルキル基、Ｒ³は炭素数１〜６のアルキレン基、好ましくは直鎖もしくは分岐鎖のアルキレン基又は炭素数２〜６のアルケニレン基、好ましくは直鎖もしくは分岐鎖のアルケニレン基を示す。）で表されるアミドアルコール化合物、下記式２：

（式中、Ｒ⁴は、炭素数７〜１９の炭化水素基、好ましくは直鎖もしくは分岐鎖のアルキル基又はアルケニル基、Ｒ⁵は、−ＣＨ₂ＣＯＯＭ、−ＣＨ₂ＣＨ₂ＣＯＯＭ又は−ＣＨ₂ＣＨ（ＯＨ）ＣＨ₂ＳＯ₃Ｍ（Ｍは水素原子、アルカリ金属、アルカリ土類金属、アンモニウム又はアルカノールアミンである）、Ｒ⁶及びＲ⁷は、それぞれ独立して炭素数２〜６のアルキレン基、好ましくは直鎖もしくは分岐鎖のアルキレン基を示す。）で表されるアミドアミン型化合物、下記式３：

（式中、Ｒ⁸は、炭素数７〜１９の炭化水素基、好ましくは直鎖もしくは分岐鎖のアルキル基又はアルケニル基、Ｒ⁹は、−ＣＨ₂ＣＯＯＭ、−ＣＨ₂ＣＨ₂ＣＯＯＭ又は−ＣＨ₂ＣＨ（ＯＨ）ＣＨ₂ＳＯ₃Ｍ（Ｍは水素原子、アルカリ金属、アルカリ土類金属、アンモニウム又はアルカノールアミンである）、Ｒ¹⁰は水素原子、−ＣＨ₂ＣＯＯＭ、−ＣＨ₂ＣＨ₂ＣＯＯＭ又は−ＣＨ₂ＣＨ（ＯＨ）ＣＨ₂ＳＯ₃Ｍ（Ｍは前記と同じである）、Ｒ¹¹は炭素数１〜６のアルキル基もしくはヒドロキシアルキル基、好ましくは直鎖あるいは分岐のアルキル基もしくはヒドロキシアルキル基、あるいは水素原子、Ｒ¹²は、炭素数２〜６のアルキレン基、好ましくは直鎖もしくは分岐鎖のアルキレン基を示す。）で表されるアミドアミン型化合物、下記式４：

（式中、Ｒ¹³は炭素数８〜１８の炭化水素基、好ましくは直鎖もしくは分岐鎖のアルキル基又はアルケニル基、あるいはＲ¹⁴ＣＯＮＨ（ＣＨ₂）_a−（Ｒ¹⁴ＣＯは炭素数８〜１８のアシル基、ａは２〜４の整数である）で表される基、Ｘ^-は−ＣＨ₂ＣＨ（ＯＨ）ＣＨ₂ＳＯ₃ ^-基又は−ＣＨ₂ＣＯＯ^-基を示す。）で表されるベタイン型化合物、及び、下記式５：

（式中、Ｒ¹⁶は炭素数８〜１８の炭化水素基、好ましくは直鎖もしくは分岐鎖のアルキル基又はアルケニル基を示す。）で表されるイミダゾリン型化合物からなる群より選ばれる少なくとも１種の化合物である高濃度アニオン界面活性剤用添加剤、及び
（２）前記高濃度アニオン界面活性剤用添加剤、下記式６：
ＲＯ（ＡＯ）_mＳＯ₃Ｍ¹ （６）
（式中、Ｒは炭素数９〜２４の炭化水素基、好ましくは直鎖もしくは分岐鎖のアルキル基又はアルケニル基、Ａは炭素数２〜４のアルキレン基、Ｍ¹は水素原子、アルカリ金属又はＮＨ₄、ｍは平均値で０〜４の数を示す）で表される化合物を１種以上、及び水を含むアニオン界面活性剤組成物、
を提供する。 That is, the present invention
(1) An additive for high concentration anionic surfactant comprising a nitrogen-containing compound, wherein the nitrogen-containing compound is represented by the following formula 1:

(In the formula, R ¹ is a hydrocarbon group optionally having a hydroxyl group having 5 to 23 carbon atoms, preferably a linear or branched alkyl group or alkenyl group, R ² is a hydrogen atom, or 1 to 1 carbon atoms. 3 alkyl group, preferably a linear or branched alkyl group, R ³ is an alkylene group having 1 to 6 carbon atoms, preferably a linear or branched alkylene group or an alkenylene group having 2 to 6 carbon atoms, preferably An amide alcohol compound represented by the following formula 2:

(Wherein R ⁴ is a hydrocarbon group having 7 to 19 carbon atoms, preferably a linear or branched alkyl group or alkenyl group, R ⁵ is —CH ₂ COOM, —CH ₂ CH ₂ COOM or —CH ₂ CH (OH) CH ₂ SO ₃ M (M is a hydrogen atom, alkali metal, alkaline earth metal, ammonium or alkanolamine), R ⁶ and R ⁷ are each independently an alkylene having 2 to 6 carbon atoms. An amidoamine type compound represented by the following formula 3:

(Wherein R ⁸ is a hydrocarbon group having 7 to 19 carbon atoms, preferably a linear or branched alkyl group or alkenyl group, and R ⁹ is —CH ₂ COOM, —CH ₂ CH ₂ COOM or —CH. ₂ CH (OH) CH ₂ SO ₃ M (M is a hydrogen atom, alkali metal, alkaline earth metal, ammonium or alkanolamine), R ¹⁰ is a hydrogen atom, —CH ₂ COOM, —CH ₂ CH ₂ COOM or —CH ₂ CH (OH) CH ₂ SO ₃ M (M is the same as above), R ¹¹ is an alkyl group or hydroxyalkyl group having 1 to 6 carbon atoms, preferably a linear or branched alkyl group or hydroxyalkyl. Or a hydrogen atom, R ¹² represents an alkylene group having 2 to 6 carbon atoms, preferably a linear or branched alkylene group.) Formula 4:

(In the formula, R ¹³ is a hydrocarbon group having 8 to 18 carbon atoms, preferably a linear or branched alkyl group or alkenyl group, or R ¹⁴ CONH (CH ₂ ) _a — (R ¹⁴ CO has 8 to 8 carbon atoms). 18 is an acyl group, a is an integer of 2 to 4, and X ⁻ represents a —CH ₂ CH (OH) CH ₂ SO ₃ ^— group or a —CH ₂ COO ^— group. Betaine-type compound, and the following formula 5:

(Wherein R ¹⁶ represents a hydrocarbon group having 8 to 18 carbon atoms, preferably a linear or branched alkyl group or alkenyl group). At least one selected from the group consisting of imidazoline type compounds represented by An additive for high concentration anionic surfactant, which is a compound of (2), and (2) the additive for high concentration anionic surfactant, the following formula 6:
RO (AO) _m SO ₃ M ¹ (6)
Wherein R is a hydrocarbon group having 9 to 24 carbon atoms, preferably a linear or branched alkyl group or alkenyl group, A is an alkylene group having 2 to 4 carbon atoms, M ¹ is a hydrogen atom, an alkali metal or NH ₄ , m represents an average value of 0 to 4), an anionic surfactant composition containing one or more compounds represented by water and water,
I will provide a.

  According to the present invention, a novel additive useful for fluidizing a high concentration alkyl sulfate and / or alkyl ether sulfate composition can be provided. Furthermore, according to this invention, the anionic surfactant composition containing the high concentration alkyl sulfate and / or alkyl ether sulfate which has favorable fluidity | liquidity can be provided by including the said additive. Specifically, handling at the time of handling can be greatly improved by the action of widening the width of the paste-like concentration region.

  The additive for high concentration anionic surfactant of the present invention contains one or more nitrogen-containing compounds. From the viewpoint of the effect as a fluidizing agent of a composition such as alkyl sulfate (AS) or alkyl ether sulfate (ES), the nitrogen-containing compounds include the following amide alcohol compounds, amide amine type compounds, betaine type compounds, and imidazolines. Type compounds are preferred.

で表される化合物を用いることができる。 Examples of the amide alcohol compound include the following formula 1:

The compound represented by these can be used.

In Formula 1, R ¹ represents a hydrocarbon group which may have a hydroxyl group having 5 to 23 carbon atoms, preferably a linear or branched alkyl group or alkenyl group. Preferably, the carbon number is 7-19. Examples of the acyl group represented by R ¹ CO— include octanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, docosanoic acid, linoleic acid, 2-ethylhexanoic acid, 2-octylundecanoic acid. , Acyl groups derived from isostearic acid, oleic acid, coconut fatty acid, palm oil fatty acid, palm kernel oil fatty acid, beef tallow fatty acid, etc., particularly preferably octanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid , Octadecanoic acid. It is an acyl group derived from oleic acid, coconut fatty acid, palm oil fatty acid, palm kernel oil fatty acid, and beef tallow fatty acid. The amide alcohol compound may be a compound represented by the formula 1 or a mixture thereof. It is preferable that 50% by mass or more of the acyl group in the amide alcohol compound is an acyl group derived from a fatty acid having 12 to 14 carbon atoms, and 40% by mass or more and less than 100% by mass is derived from a fatty acid having 12 carbon atoms. More preferred is an acyl group.

R ² is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, preferably a linear or branched alkyl group, preferably a methyl group, an ethyl group, particularly preferably a methyl group. R ³ is an alkylene group having 1 to 6 carbon atoms, preferably a linear or branched alkylene group or an alkenylene group having 2 to 6 carbon atoms, preferably a linear or branched alkenylene group, preferably carbon. It is a linear or branched alkylene group of the number 2 or 3.

  Specific examples of the amide alcohol compound of the formula 1 include N-ethanol-N-methyloctanoic acid amide, N-ethanol-N-methyldecanoic acid amide, N-ethanol-N-methyldodecanoic acid amide, N-ethanol-N. -Methyltetradecanoic acid amide, N-ethanol-N-methylhexadecanoic acid amide, N-ethanol-N-methyloctadecanoic acid amide, N-ethanol-N-methylcoconut fatty acid amide, N-ethanol-N-methyl palm kernel fatty acid amide N-isopropanol-N-ethyldodecanoic acid amide, N-ethyl-N-isopropanol oleic acid amide, N-ethyl-N-isopropanol isostearic acid amide and the like.

  The method for producing the amide alcohol compound represented by Formula 1 is not particularly limited. For example, a dehydration reaction between a fatty acid and an alkanolamine, a reaction between a fatty acid halide and an alkanolamine, or an oil or fatty acid lower alcohol ester and an alkanolamine. After the ester-amide exchange reaction in the presence of an alkali catalyst, it can be purified and produced by steam distillation or the like. The products obtained by these methods may contain a small amount of alkanolamine, fatty acid, inorganic salt, glycerin, etc., but these may interfere with the performance as an additive for high concentration anionic surfactant. There is no degree.

で表される化合物を用いることができる。 Examples of the amidoamine type compound include the following formula 2:

The compound represented by these can be used.

In Formula 2, R ⁴ represents a hydrocarbon group having 7 to 19 carbon atoms, preferably a linear or branched alkyl group or alkenyl group, and preferably an alkyl group having 11 to 15 carbon atoms. As the acyl group represented by R ⁴ CO—, a lauroyl group, a myristoyl group, a palmitoyl group, and a cocoyl group are preferable.
R ⁵ represents —CH ₂ COOM, —CH ₂ CH ₂ COOM, or —CH ₂ CH (OH) CH ₂ SO ₃ M. M is a hydrogen atom, an alkali metal such as sodium or potassium, an alkaline earth metal such as calcium or magnesium, or an alkanolamine such as ammonium or triethanolamine, with alkali metals and alkanolamines being particularly preferred.
The amidoamine type compound may be a compound represented by the formula 2 or a mixture thereof. It is preferable that 50% by mass or more of the acyl group in the present compound is an acyl group derived from a fatty acid having 12 to 14 carbon atoms, and 40% by mass or more and less than 100% by mass is derived from a fatty acid having 12 carbon atoms. And more preferably an acyl group.
R ⁶ and R ⁷ each independently represents an alkylene group having 2 to 6 carbon atoms, preferably a linear or branched alkylene group, preferably an ethylene group.

  Specific examples of the compound represented by Formula 2 include N-lauroyl-N′-carboxymethyl-N ′-(2-hydroxyethyl) ethylenediamine, N-lauroyl-N′-carboxyethyl-N ′-(2 -Hydroxyethyl) ethylenediamine, N-myristoyl-N'-carboxymethyl-N '-(2-hydroxyethyl) ethylenediamine, N-myristoyl-N'-carboxyethyl-N'-(2-hydroxyethyl) ethylenediamine, N- Cocoyl-N′-carboxymethyl-N ′-(2-hydroxyethyl) ethylenediamine, N-cocoyl-N′-carboxyethyl-N ′-(2-hydroxyethyl) ethylenediamine, N-palmitoyl-N′-carboxymethyl- N ′-(2-hydroxyethyl) ethylenediamine, N-par Mitoiru -N'- carboxyethyl -N '- (2-hydroxyethyl) ethylenediamine and salts thereof.

で表される化合物が挙げられる。 Other examples of the amidoamine type compound include the following formula 3:

The compound represented by these is mentioned.

In Formula 3, R ⁸ represents a hydrocarbon group having 7 to 19 carbon atoms, preferably a linear or branched alkyl group or alkenyl group, and preferably an alkyl group having 11 to 15 carbon atoms. As the acyl group represented by R ⁸ CO—, a lauroyl group, a myristoyl group, a palmitoyl group, and a cocoyl group are preferable.
The amidoamine type compound may be a compound represented by Formula 3 or a mixture thereof. It is preferable that 50% by mass or more of the acyl group in the present compound is an acyl group derived from a fatty acid having 12 to 14 carbon atoms, and 40% by mass or more and less than 100% by mass is derived from a fatty acid having 12 carbon atoms. And more preferably an acyl group.
R ⁹ represents —CH ₂ COOM, —CH ₂ CH ₂ COOM or —CH ₂ CH (OH) CH ₂ SO ₃ M, and R ¹⁰ represents a hydrogen atom, —CH ₂ COOM, —CH ₂ CH ₂ COOM or — CH ₂ CH (OH) CH ₂ SO ₃ M is shown. M is a hydrogen atom, an alkali metal such as sodium or potassium, an alkaline earth metal such as calcium or magnesium, or an alkanolamine such as ammonium or triethanolamine, with alkali metals and alkanolamines being particularly preferred.
R ¹¹ is an alkyl group or hydroxyalkyl group having 1 to 6 carbon atoms, preferably a linear or branched alkyl group or hydroxyalkyl group, and R ¹² is an alkylene group having 2 to 6 carbon atoms, preferably a linear or branched chain. Represents an alkylene group, preferably an ethylene group.

  Specific examples of the compound represented by Formula 3 include N-lauroyl-N- (2-hydroxyethyl) -N′-carboxymethylethylenediamine, N-lauroyl-N- (2-hydroxyethyl) -N ′, N′-bis (carboxymethyl) ethylenediamine, N-lauroyl-N- (2-hydroxyethyl) -N ′, N′-bis (carboxyethyl) ethylenediamine, N-myristoyl-N- (2-hydroxyethyl) -N '-Carboxymethylethylenediamine, N-myristoyl-N- (2-hydroxyethyl) -N', N'-bis (carboxymethyl) ethylenediamine, N-myristoyl-N- (2-hydroxyethyl) -N ', N' -Bis (carboxyethyl) ethylenediamine, N-cocoyl-N- (2-hydroxyethyl) -N -Carboxymethylethylenediamine, N-cocoyl-N- (2-hydroxyethyl) -N ', N'-bis (carboxymethyl) ethylenediamine, N-cocoyl-N- (2-hydroxyethyl) -N', N'- Bis (carboxyethyl) ethylenediamine, N-palmitoyl-N- (2-hydroxyethyl) -N′-carboxymethylethylenediamine, N-palmitoyl-N- (2-hydroxyethyl) -N ′, N′-bis (carboxymethyl) ) Ethylenediamine, N-palmitoyl-N- (2-hydroxyethyl) -N ′, N′-bis (carboxyethyl) ethylenediamine, and salts thereof.

  The amidoamine type compounds of the formulas 2 and 3 can be obtained, for example, by reacting 1 mol of an imidazoline derivative with 1 to 2 mol of monochloroacetic acid, acrylic acid or the like.

で表される化合物を用いることができる。 Examples of the betaine type compound include the following formula 4:

The compound represented by these can be used.

In Formula 4, R ¹³ is a hydrocarbon group having 8 to 18 carbon atoms, preferably 10 to 14 carbon atoms, preferably a linear or branched alkyl group or alkenyl group, or R ¹⁴ CONH (CH ₂ ) _a — (R ¹⁴ CO represents a group represented by an acyl group having 8 to 18 carbon atoms, preferably 10 to 14 carbon atoms, and a is an integer of 2 to 4, preferably 3. R ¹³ and R ¹⁴ CO are mixed alkyls derived from animal oils such as beef tallow and lard, or vegetable oils such as soybean oil, coconut oil and palm kernel oil, or synthetic oils, and mixed oils thereof. It may be a group, an alkenyl group or an acyl group. Particularly preferred are mixed alkyl groups or acyl groups derived from palm oil or palm kernel oil.
The betaine type compound may be a compound represented by the formula 4 alone or a mixture thereof. It is preferable that 50% by mass or more of the acyl group in the present compound is an acyl group derived from a fatty acid having 12 to 14 carbon atoms, and 40% by mass or more and less than 100% by mass is derived from a fatty acid having 12 carbon atoms. And more preferably an acyl group.
X ⁻ represents a —CH ₂ CH (OH) CH ₂ SO ₃ ^— group or a —CH ₂ COO ^— group.

Examples of the betaine type compound represented by the formula 4 include hydroxysulfobetaines in which R ¹³ is an alkyl group or alkenyl group having 8 to 18 carbon atoms, and X ⁻ is —CH ₂ CH (OH) CH ₂ SO ₃ ^— . Amidopropylcarboxybetaine in which R ¹³ is R ¹⁴ CONHC ₃ H ₆ — (R ¹⁴ CO is the same as described above) and X ⁻ is —CH ₂ COO ₂ ^— is preferable.

Specific examples of the betaine type compound represented by the formula 4 include lauryldimethylhydroxysulfobetaine represented by the following formula (4-1) and lauroylaminopropyldimethylcarboxybetaine represented by the formula (4-2). And coconut oil fatty acid amidopropyldimethylcarboxybetaine represented by the formula (4-3).

で表される化合物を用いることができる。 As an imidazoline type compound, the following formula 5:

The compound represented by these can be used.

In the formula 5, R ¹⁶ represents a hydrocarbon group having 8 to 18 carbon atoms, preferably 10 to 14 carbon atoms, preferably a linear or branched alkyl group or alkenyl group. Natural oils such as bean oil, coconut oil, balm kernel oil, or synthetic oils, and mixed alkyl groups or alkenyl groups derived from mixed oils thereof.

The additive for high-concentration anionic surfactants of the present invention contains one or more nitrogen-containing compounds of the above formulas 1 to 5. When two or more types are included, the mixing ratio is arbitrary, and there is no problem in performance as an additive for high concentration anionic surfactant.
Here, “high concentration” means that the mixture with water contains a large amount of an anionic surfactant, and for example, the content of the anionic surfactant is preferably 40% by mass or more, more preferably 50% by mass. % Of the composition. The upper limit of the content of the anionic surfactant is not particularly limited, but the content is preferably 90% by mass or less, more preferably 75% by mass or less.

The anionic surfactant composition of the present invention is a high-concentration anionic surfactant additive containing one or more compounds of the nitrogen-containing compound represented by the formulas 1 to 5, the following formula 6:
RO (AO) _m SO ₃ M ¹ (6)
1 or more types of compounds, such as alkyl sulfate (AS) and alkyl ether sulfate (ES) represented by these, and water are included.

  In Formula 6, R is a hydrocarbon group having 9 to 24 carbon atoms, preferably 12 to 20 carbon atoms, preferably a linear or branched alkyl group or alkenyl group. When the carbon number of R is 9 to 24, the resulting compound of formula 6 has a good balance of surface activity and solubility in water. The alkyl group and alkenyl group may be either linear or branched. Specifically, the decyl group, dodecyl group, tetradecyl group, hexadecyl group, octadecyl group, icosyl group, docosyl group, oleyl group, ( Each substituent includes an isomer thereof).

The alkylene group having 2 to 4 carbon atoms represented by A may be linear or branched, and examples thereof include an ethylene group, a propylene group, a 1-methyltrimethylene group, a trimethylene group, and a tetramethylene group. Among these, an ethylene group or a propylene group is preferable, and an ethylene group is more preferable.
M ¹ represents a hydrogen atom, an alkali metal or NH ₄ . Examples of the alkali metal include sodium, potassium, and lithium. Among these, sodium or potassium is preferable, and sodium is more preferable.
m is an average value of 0 to 4, preferably 0.1 to 2, and more preferably 0.5 to 1.5.

  The content of the high-concentration anionic surfactant additive in the anionic surfactant composition of the present invention varies depending on the type of the compound of formula 6 and the type of the additive. 0.1-50 mass parts is preferable with respect to 100 mass parts of compounds, More preferably, it is 1-30 mass parts, Most preferably, it is 2-20 mass parts. Thus, by adding the additive for high concentration anionic surfactant of the present invention to the compound of formula 6, even a composition containing the compound of formula 6 at a high concentration exhibits good fluidity and handling. Sexuality improves. The content of water is preferably 10 to 60 parts by mass, more preferably 20 to 50 parts by mass, and particularly preferably 25 to 40 parts by mass with respect to 100 parts by mass of the compound of formula 6.

The anionic surfactant composition of the present invention is a composition comprising substantially the majority of an anionic surfactant represented by formula 6, a nitrogen-containing compound represented by formulas 1 to 5 and water. It is. In particular, even if it does not contain other flow aids such as inorganic salts, it exhibits good flowability and can be an intermediate product such as a detergent as an anionic surfactant premix. That is, the anionic surfactant composition of the present invention is characterized by excellent fluidity, and the composition having good handling properties can be used as a raw material for shampoos and liquid whole body cleaning agents.
In general, an inorganic salt or the like is sometimes used as a viscosity modifier in a surfactant composition. However, when an inorganic salt is added, it is necessary to adjust the viscosity again in a product such as a shampoo. On the other hand, the anionic surfactant composition of the present invention is a premix containing an anionic surfactant (compound of formula 6) and an auxiliary surfactant (nitrogen-containing compound of formulas 1 to 5) as active ingredients. In addition, an inorganic salt is not necessarily required, and a degree of freedom can be given to viscosity adjustment of a shampoo or the like.
The anionic surfactant premix of the present invention preferably has a pH in the vicinity of the neutral region in order to stabilize the composition in the system, specifically 5 to 8, more preferably 5.5 to 7.5. It is preferable to do. For that purpose, for example, it is desirable to include a pH buffer such as phosphoric acid, citric acid, and polybasic acid.
The anionic surfactant composition of the present invention can be produced according to a conventional method, and can be suitably used for a liquid detergent composition. If necessary, auxiliary agents such as pigments, fragrances, solubilizers, and builders can be appropriately added to the liquid detergent composition. Furthermore, other anionic surfactants, cationic surfactants, amphoteric surfactants, nonionic surfactants and the like can be added for the purpose of adjusting detergency and foaming. The liquid detergent composition is used for shampoos, body shampoos, kitchen detergents, liquid soaps, and the like.

Synthesis example (AO addition)
According to a conventional method, ethylene oxide (EO) was introduced into a higher alcohol having 12/14 carbon atoms placed in a pressure resistant reactor in the presence of a catalyst to obtain an EO adduct of alcohol. The resulting alcohol EO adduct was then sulfated as follows.
Synthesis example (sulfation)
After sulfating 12/14 higher alcohol ethoxylate (average added mole number of ethylene oxide 1.0) with SO ₃ gas in a conventional manner using a thin film type continuous sulfation facility, 26 mass% aqueous sodium hydroxide solution The solution was charged into the solution and neutralized to obtain an aqueous anionic surfactant solution (water content: 28% by mass).

Examples 1-7
Add the additives shown in Table 1 to the aqueous anionic surfactant solution obtained in the synthesis example, dilute with water or concentrate using a rotary evaporator as necessary, and after cooling, remove bubbles under reduced pressure. And an anionic surfactant composition was obtained.
The fluidity of each anionic surfactant composition was evaluated by the method shown below. That is, 15 mL of the sample composition was placed in a vertically-arranged cylindrical glass tube having an inner diameter of 10 mm, and the upper portion was capped and allowed to stand sufficiently at each temperature described in the table. After standing, the time required for removing the stopper and moving the lower end of the sample by 10 cm was used as an indicator of fluidity.
The results are shown in Table 1 together with the additive content and anionic surfactant concentration.

Comparative Examples 1-4
The anionic surfactant aqueous solution obtained in the synthesis example was subjected to bubble removal treatment under reduced pressure without adding an additive, and this anionic surfactant aqueous solution was evaluated for fluidity in the same manner as described above. It was.
The results are shown in Table 1 together with the anionic surfactant concentration.

  As described above, the additive for high-concentration anionic surfactant of the present invention containing a nitrogen-containing compound is useful as a fluidizing agent for alkyl sulfate and / or alkyl ether sulfate compositions, and by using it, A high concentration of alkyl sulfate and / or alkyl ether sulfate-containing anionic surfactant composition having good fluidity is obtained.

Claims (4)

A high concentration anionic surfactant additive comprising a nitrogen-containing compound, wherein the nitrogen-containing compound is represented by the following formula 1:

(In the formula, R ¹ is a hydrocarbon group which may have a hydroxyl group having 5 to 23 carbon atoms, R ² is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R ³ has 1 to 6 carbon atoms. An alkylene group or an alkenylene group having 2 to 6 carbon atoms.)
Following formula 2:

(Wherein R ⁴ is a hydrocarbon group having 7 to 19 carbon atoms, R ⁵ is —CH ₂ COOM, —CH ₂ CH ₂ COOM or —CH ₂ CH (OH) CH ₂ SO ₃ M (M is hydrogen) An atom, an alkali metal, an alkaline earth metal, ammonium or an alkanolamine), R ⁶ and R ⁷ each independently represents an alkylene group having 2 to 6 carbon atoms.)
Formula 3 below:

(Wherein R ⁸ is a hydrocarbon group having 7 to 19 carbon atoms, and R ⁹ is —CH ₂ COOM, —CH ₂ CH ₂ COOM, or —CH ₂ CH (OH) CH ₂ SO ₃ M (M is A hydrogen atom, an alkali metal, an alkaline earth metal, ammonium or alkanolamine), R ¹⁰ is a hydrogen atom, —CH ₂ COOM, —CH ₂ CH ₂ COOM or —CH ₂ CH (OH) CH ₂ SO ₃ M ( M is the same as described above), R ¹¹ represents an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group, or a hydrogen atom, and R ¹² represents an alkylene group having 2 to 6 carbon atoms. Type compound,
Following formula 4:

(In the formula, R ¹³ is a hydrocarbon group having 8 to 18 carbon atoms, or R ¹⁴ CONH (CH ₂ ) _a- (R ¹⁴ CO is an acyl group having 8 to 18 carbon atoms, and a is an integer of 2 to 4). X ⁻ represents a —CH ₂ CH (OH) CH ₂ SO ₃ ^— group or a —CH ₂ COO ^— group.), And a betaine type compound represented by:
Formula 5 below:

(Wherein, R ¹⁶ represents. A hydrocarbon group having 8 to 18 carbon atoms) high concentration anionic surfactant additive is at least one compound selected from the group consisting of imidazoline-type compounds represented by. The additive for high concentration anionic surfactant according to claim 1, the following formula 6:
RO (AO) _m SO ₃ M ¹ (6)
(In the formula, R is a hydrocarbon group having 9 to 24 carbon atoms, A is an alkylene group having 2 to 4 carbon atoms, M ¹ is a hydrogen atom, an alkali metal or NH ₄ , and m is an average value of 0 to 4) An anionic surfactant composition containing one or more compounds represented by (1) and water. The high-concentration anionic surfactant additive according to claim 1 is contained in an amount of 0.1 to 50 parts by mass and water in a proportion of 10 to 60 parts by mass with respect to 100 parts by mass of the compound of formula 6. An anionic surfactant composition described in 1.   An anionic surfactant premix comprising one or more compounds of formula 6 as a main component, one or more nitrogen-containing compounds represented by formulas 1 to 5 and water.