JP2002356697A - Surface active agent and its application - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide polyoxyalkylene glycol monoalkylamide nonionic and anionic surface active agents having excellent stability with time, compoundability, foaming ability and less stimulation to skin, and to provide a detergent, a viscosity improver, an emulsifier, a dispersing agent, a dissolving agent, a penetrating agent and a wetting agent each containing the same. SOLUTION: The nonionic or anionic surface active agent is represented by the formula: R<1> -CONH-(AO)n -X (1) (R<1> is a 7-24C hydrocarbon group; X is a hydrogen atom or an anionic group; A is one or more 2-5C alkylene groups; and n is one or more integers the average of which is 1.5 to 20) and comprises component having different n values wherein the sum of the components of nmax ±1 is not less than 80 wt.%, nmax being an n value of the component of the largest weight %. A detergent, a viscosity improver, an emulsifier, a dispersing agent, a dissolving agent, a penetrating agent and a wetting agent contain the surface active agents.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a surfactant. More specifically, it relates to a polyoxyalkylene glycol monoalkylamide type nonionic surfactant and an anionized product thereof.

[0002]

2. Description of the Related Art Polyoxyalkylene glycol monoalkylamide type nonionic surfactants have been proposed (JP-A-56-08896).
It is known that this type of nonionic surfactant has a thickening effect on various anionic surfactants and the like. Alkyl amide ether sulfates (JP-A-5-339596), alkyl amide sulfosuccinates (JP-B 5-75722), and alkyl amide ether carboxylic acids as anionized products of these nonionic surfactants Salt (JP-A-11-18
No. 9786), and these anionic surfactants are used as components of shampoos, dishwashing detergents, metal detergents, polymerization emulsifiers and the like.

[0003]

However, when these polyoxyalkylene glycol monoalkylamide type nonionic surfactants are blended in a detergent composition, the stability of the product over time, such as a hazy appearance, and the like, Problems such as insufficient thickening remain. Further, anionic surfactants obtained by anionizing these,
When formulated in a detergent composition, it has poor day-to-day stability such as blurred appearance of the product when stored at low temperatures for a long period of time, and has insufficient foaming and detergency, and furthermore, skin irritation to the human body Problems such as being strong were left.

[0004]

The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have found that a polyoxyalkylene glycol monoalkylamide type nonionic surfactant having a narrow molecular weight distribution of a polyoxyalkylene glycol moiety. Further, the inventors have found that the anionized product thereof has excellent thickening properties, compoundability, foaming power, detergency, low-temperature stability, and water resistance to hard water, and have reached the present invention.

That is, the present invention relates to a surfactant represented by the following general formula (1), comprising components having different n, wherein n is the _maximum component by weight and n _max is defined as n _max
Nonionic or anionic surfactants having a total of components in the range of ± ₁ of 80% by weight or more, and detergents, thickeners, emulsifiers, dispersants containing these surfactants,
Solubilizers, penetrants and wetting agents. R ¹ -CONH- (AO) _n -X (1) [wherein, R ¹ is a hydrocarbon group having 7 to 24 carbon atoms, X is a hydrogen atom or an anionic group, and A is one type having 2 to 5 carbon atoms. The above alkylene group and n represent an integer of 1 or more with an average of 1.5 to 20. ]

[0006]

BEST MODE FOR CARRYING OUT THE INVENTION The surfactant in the present invention is represented by the general formula (1), wherein n represents the number of moles of (AO), and has an average of 1.5 to 20, preferably 1.5. 10 to 10, more preferably 1.5 to 5 or more (preferably 1 to 5).
To 20). In the surfactant of the present invention, among the n, the component having the largest weight% is defined as n
_{When max} is used, the total of components within the range of n _max ± ₁ needs to be 80% by weight or more, and preferably 90% by weight or more. If it is less than 80% by weight, the stability over time and the detergency at a low concentration are reduced.

The weight% of each component of n is measured by the following method using high performance liquid chromatography or gas chromatography.

[0008] In the case of a nonionic surfactant: a sample is reacted with an excess of phenylisocyanate (reagent grade) to label a hydroxyl group, and then measured by high performance liquid chromatography under the following conditions. <Measurement conditions> Model: LC-10ADVP manufactured by Shimadzu Corporation Column: μ-Porasil (Waters) Detector: UV (240 nm) Temperature: 40 ° C Eluent: 2% isopropyl alcohol / butyl chloride to 32% isopropyl alcohol / butyl Gradient up to chloride Measurement time: 1 hour

In the case of an anionic surfactant; in the case where the anionic group is a sulfonic acid group, a sulfate ester group, a phosphate ester group or a salt thereof: Measured by high performance liquid chromatography under the following conditions. When the anionic group is a carboxylic acid group or a salt thereof: the sample is reacted with excess methanol using concentrated sulfuric acid as a catalyst to esterify the mixture, and after neutralization, the petroleum ether extract is measured by gas chromatography under the following conditions. <Measurement conditions> Model: GC-14A manufactured by Shimadzu Column: DIASOLID ZT (80-100 mesh) Detector: FID Temperature: 100 → 320 ° C (10 ° C / min) Carrier gas: N ₂ , 40 mL / min Measurement Time: 30 minutes

In the general formula (1), R ¹ has 7 to 2 carbon atoms.
Examples of the hydrocarbon group of No. 4 include a linear or branched aliphatic hydrocarbon group (such as an alkyl group, an alkenyl group, and an alkadienyl group), and a substituted aromatic hydrocarbon group (such as a substituted aryl group and a substituted arylalkyl group) or a non-cyclic hydrocarbon group. Examples include a substituted aromatic hydrocarbon group (an unsubstituted aryl group, an unsubstituted arylalkyl group, and the like), and specific examples include the following groups.

Aliphatic hydrocarbon group; alkyl group [n-octyl, 2-ethylhexyl, n- and i-nonyl, n
-And i-decyl, 2-ethyloctyl, lauryl,
Tridecyl, myristyl, cetyl, stearyl and nonadecyl groups etc.), alkenyl groups [octenyl, decenyl, dodecenyl, tridecenyl, pentadecenyl, oleyl and gadreyl groups etc.], alkadienyl groups [linoleyl groups etc.],

Substituted aromatic hydrocarbon groups; substituted aryl groups [nonylphenyl, octylphenyl and tert-butylphenyl groups and the like], substituted arylalkyl groups [ethylbenzyl, n- and i-propylbenzyl, n- and i-hexyl] Alkyl-substituted arylalkyl groups such as benzyl and n-octylbenzyl groups, and aromatic hydrocarbon-substituted arylalkyl groups such as styrenated benzyl groups],

Unsubstituted aromatic hydrocarbon group; unsubstituted aryl group [phenyl and naphthyl group etc.], unsubstituted arylalkyl group [benzyl and phenylethyl group etc.].

R ¹ may be a mixture of two or more groups such as linear and branched. R ¹ preferably has 9 to 9 carbon atoms.
21, more preferably 10 to 18 carbon atoms. If the number of carbon atoms is less than 7, sufficient foaming power and detergency cannot be obtained, and if the number of carbon atoms exceeds 24, the solubility is significantly reduced.

A is a linear or branched alkylene group having 2 to 5 carbon atoms. As the alkylene group, ethylene,
1,2- and 1,3-propylene, 1,2-, 1,3
-, 1,4- and 2,3-butylene, 1,2-, 1,
Examples include 3-, 1,4-, 1,5-, 2,3- and 2,4-pentene groups, and combinations of two or more of these. Of these, ethylene groups and 1,2-propylene groups are preferred, and when A is two or more types, they may be block-shaped, random-shaped, or a combination of both. A is an oxyalkylene group together with an oxygen atom O
AO- is formed.

N corresponds to the number of moles of the oxyalkylene group -AO-, n is an integer of 1 or more, preferably 1 to 20, and the average of n is 1.5 to 20, preferably 1.5 to 20.
10, and more preferably an integer of 1.5 to 5. When the average of n is 5 or less, sufficient foaming power and cleaning power are easily obtained.

Specific examples of the nonionic surfactant when X is a hydrogen atom include diethylene glycol monolauric amide, tetrapropylene glycol monolauric amide, triethylene glycol monomyristate amide, dipropylene glycol monomyristate amide, and pentane. Ethylene glycol monopalmitate, dipropylene glycol monostearate, and the like.

When X is an anionic group, general formula (1) represents an anionic surfactant, and examples of X include groups containing a carboxyl group, a sulfonic group, a sulfate group, a phosphate group, and the like. Of these, the following general formulas (4) to
It is a group represented by (7).

-(CH ₂ ) _p CH ₂ COOM _{1 / r} (4)-(CH ₂ ) _p SO ₃ M _{1 / r} (5)

[0020]

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[0021]

Embedded image

In the formula, p is 0 or an integer of 1 to 5,
P in the general formula (4) is preferably 0 or 1, and p in the general formula (5) is preferably 0 or 2. L
One is SO ₃ M _{1 / r} and the other is a hydrogen atom. M represents a hydrogen atom or a cation having r valence, r is 1 or 2,
Preferably it is 1.

Examples of the r-valent cation represented by M in the general formulas (4) to (7) include alkali metals (eg, sodium, potassium, lithium), alkaline earth metals (eg, calcium, magnesium, barium), and organic compounds. Amine cations and quaternary ammonium cations are mentioned.

Examples of the organic amine constituting the organic amine cation include aliphatic amines, alicyclic amines, heterocyclic amines, alkanolamines, and alkylene oxide (hereinafter abbreviated as AO) adducts thereof. As the aliphatic amine, methylamine, dimethylamine,
Mono-, di-, and tri-alkyl having 1 to 18 carbon atoms in an alkyl group such as trimethylamine, triethylamine, hexylamine, octylamine, methylhexylamine, dimethylhexylamine, dimethyloctylamine, dimethyllaurylamine, and dimethylcetylamine. Amines. Examples of the alicyclic amine include cycloalkylamines having 4 to 12 carbon atoms such as cyclobutylamine, cyclohexylamine, cyclopentylamine, cyclooctylamine, N-methylcyclohexylamine and N-ethylcyclohexylamine, and Alkyl (C1-6)
Substituents are mentioned. Examples of the heterocyclic amine include a heterocyclic amine having 4 to 10 carbon atoms such as morpholine,
As alkanolamines, monoethanolamine,
Hydroxyalkyl groups such as diethanolamine and triethanolamine having 2 to 8 carbon atoms are mono- and di-
And tri-hydroxyalkylamines.
As AO of these AO adducts, AO having 2 to 4 carbon atoms
O, for example, ethylene oxide (hereinafter abbreviated as EO), 1,2-propylene oxide (hereinafter abbreviated as PO), and 1,2-butylene oxide. Preferably, it is EO. The number of these added moles is usually 1 to 5 moles, preferably 1 to 2 moles per active hydrogen. Specific examples of these AO adducts include dihydroxyethylhexylamine and hydroxyethylmethylhexylamine.

Specific examples of the quaternary ammonium cation include trimethylethylammonium, triethylmethylammonium, trimethylhexylammonium, trimethyloctylammonium, tributyloctylammonium, trimethyldecylammonium, trimethyltetradecylammonium, trimethylcetylammonium and monomethyltrioctyl. A tetraalkylammonium cation having 1 to 18 carbon atoms in an alkyl group such as ammonium; a cycloalkyl group having 4 to 12 carbon atoms in a cycloalkyl group such as N, N-dimethylcyclohexylammonium and N, N-diethylcyclohexylammonium; A cycloalkyldialkylammonium cation having 1 to 6 carbon atoms in the alkyl group; trihydroxyethylhexylammonium Carbon number of 2 to 8 and an alkyl group having carbon atoms of the hydroxyalkyl group and the like and 1-6 birds hydroxyalkyl alkyl ammonium cation. Preferred among M are alkali metals,
Organic amine cations and quaternary ammonium cations, more preferably sodium, potassium, aliphatic and alicyclic amines or their AO adducts, and quaternary ammonium cations.

Specific examples of the anionic surfactant of the present invention include a sulfate of tetraethylene glycol monolaurate, a sulfosuccinate of tripropylene glycol monolaurate, a phosphate of diethylene glycol monolaurate, and dipropylene glycol. Sulfoxide of monomyristate amide, carboxymethyl etherified product of triethylene glycol monomyristate amide, phosphate of tetraethylene glycol monopalmitate amide, sulfate of dipropylene glycol monostearate amide, and alkali metal salts thereof (Sodium salt, potassium salt, etc.), alkaline earth metal salt (calcium, magnesium salt, etc.), ammonium, organic amine salt (triethanolamine salt, trimethyla Emissions salt, triethylamine salt), and quaternary ammonium salts (tetramethylammonium salt, tetraethylammonium salt, such as benzyltrimethylammonium salts).

The nonionic surfactant of the present invention can be produced by the following method (a) or (b).

(A) An amide-forming compound represented by the following general formula (2) and a different n represented by the following general formula (3)
With a polyoxyalkylene monoamine in which the total of components within the range of n _max ± ₁ is 80% by weight or more, where n is the _maximum component by weight and n is the _maximum component. R ¹ —CO—Z (2) wherein R ¹ is the same as the group in the general formula (1);
Represents a hydroxyl group, OR ² or a halogen atom.
Here, R ² represents an alkyl group having 1 to 6 carbon atoms. _{] H 2 N- (AO) n} -H (3) [ wherein, A, n are the same as group in the general formula (1). ]

(B) Addition of AO to a carboxylic acid amide represented by the following general formula (8). R ¹ -CO-NH-Q (8) [wherein Q represents a hydrogen atom or R ³ OH. Where R ³
Represents an alkylene group having 2 to 5 carbon atoms. ]

Specific examples of the amide-forming compound represented by the general formula (2) include a carboxylic acid having the same hydrocarbon group as R ¹ in the general formula (1), an alkyl carboxylate (the alkyl group having 1 carbon atom). -6) esters and carboxylic acid halides. Among these, Z is preferably a carboxylic acid alkyl ester represented by OR ² from the viewpoint of quality of the product such as odor and hue.

Specific examples of the amide-forming compound include n
-Carboxylic acids such as octanoic acid, 2-ethylhexanoic acid, decanoic acid, lauric acid, palmitic acid, stearic acid and oleic acid, methyl esters of these carboxylic acids,
Examples include carboxylic acid esters such as ethyl ester and n-butyl ester, and chlorine, bromine or iodide of these carboxylic acids.

The polyoxyalkylene monoamine represented by the general formula (3) is obtained by adding AO to a ketiminated alkanolamine (obtained by reacting an alkanolamine and a ketone) represented by the following general formula (9). ,
Obtained by hydrolyzing the ketimine moiety. The obtained polyoxyalkylene monoamine can be easily purified by rectification or the like.

R ⁴ R ⁵ C = N-AO-H (9) wherein R ⁴ and R ^{5 each} represent a linear or branched alkyl group having 1 to 4 carbon atoms, and A represents the general formula (1) The same as in. ]

As the AO to be added to the ketiminated alkanolamine represented by the general formula (9), AO corresponding to the alkylene group A, for example, EO, PO, 1,
2-, 2,3-, 1,3- and 1,4-butylene oxide and the like.

As a catalyst for adding AO, a conventionally known catalyst can be used. For example, an acid (d1) having an acid strength H ₀ according to Hammett's acidity function of −30.0 to −11.0 and a metal salt thereof (d2); an alkali catalyst (of an alkali metal such as sodium hydroxide and potassium hydroxide); Hydroxides: hydroxides of alkaline earth metals such as magnesium hydroxide), Lewis acids (AlCl ₃ , SbCl ₅ , BF)
₃ , FeCl _3, etc.), and combinations thereof.
Preferred are (d1), (d2) and alkali catalysts.

As (d1), for example, H ₂ SO ₄ -S
O ₃ (1: 0.2 molar ratio) [H ₀ = 13.4], H ₂ SO ₄
—SO ₃ (1: 1 molar ratio) [H ₀ = 14.3], HClO
₄ [H ₀ = -13.0], ClSO ₃ H [H ₀ = -13.8], H
F-SbF ₅ (1: 0.06 molar ratio) [H ₀ = -14.
3], FSO ₃ H [H ₀ = −15.07], HF-SbF
₅ (1: 0.14 molar ratio) [H ₀ = 15.3], FSO ₃ H
—SO ₃ (1: 0.1 molar ratio) [H ₀ = −15.52], F
SO ₃ H—AsF ₅ (1: 0.05 molar ratio) [H ₀ = −1
6.61], FSO ₃ H-SbF ₅ (1: 0.05 molar ratio) [H ₀ = -18.24], HSO ₃ H-SbF ₅ (1:
0.1 mol ratio) [H ₀ = -18.94], FSO ₃ H-Sb
F ₅ (1: 0.2 molar ratio), and the super acid of [H ₀ = -20.0] and the like. Of these, preferably H ₀ = −2
5.0 to -12.5, particularly preferably -2.
It is an acid of 0.0 to -13.0.

(D2) is not particularly limited as long as it is a metal salt of (d1).
Salts such as Ca, Sr, Ba, Zn, Co, Ni, Cu, and Al may be mentioned. Preferred are metals that form divalent or higher valent salts, and particularly preferred are divalent or trivalent metals. When the acid strength H ₀ is -30.0 or more, an addition reaction of AO to a hydroxyl group easily occurs.
It is easy to obtain a product in which the sum of the components within the range of _max ± ₁ is 80% or more. The acid strength H ₀ according to Hammett's acidity function is described, for example, in “Super strong acid / super strong base” (Kodansha,
(June 1, 1988).

(D1) and (d2) may be used in combination of two or more of the above, or (d1) and (d2) may be used in combination. From the viewpoint of reaction rate and economy, the amount of the catalyst to be used is 0.00 per 100 parts by weight of the total of AO and the ketiminated monoalkanolamine of the general formula (9).
01 to 1 part by weight is preferred. More preferably 0.00
3 to 0.8 part by weight, particularly preferably 0.005 to 0.5 part
Parts by weight.

The reaction conditions for the addition of AO are not particularly limited. For example, a ketiminated monoalkanolamine represented by the above general formula (9) is mixed with a catalyst, and after substituting with nitrogen, -0.8%. under a pressure of ~5kgf / cm ^2, 80
A method in which AO is charged at a temperature of 200 to 200 ° C. and the reaction is performed until the pressure in the reaction system at 80 to 200 ° C. is equilibrated. When a plurality of types of AO are used, the addition format may be any of block addition, random addition, and a combination thereof.

Conditions for hydrolyzing the ketimine portion of the product include, for example, hydrolyzing a mixture of ketiminized monoalkanolamine AO adduct / water at a molar ratio of 1/1 to 1/2 at 100 to 200 ° C. And a method of performing dehydration and deketonization.

The polyoxyalkylene monoamine can be rectified if necessary to sharpen the molecular weight distribution. The conditions for the rectification are as follows:
At a pressure of 0 mmHg, a temperature of 50 ° C. to 250 ° C. or the like, it is obtained by fractionating a preferable one of these fractions.

Among the methods for producing the nonionic surfactant of the present invention, when Z in the method (A) is OR ² , the specific production method is the compound of the general formula (2) / the general formula (2) The molar ratio of the compound of 3) = 1 / 0.8 to 1/2, preferably 1 / 0.9 to 1 / 1.5, and the reaction temperature is 50 to 25.
R ² O at 0 ° C. until no decrease in total amine value is observed.
A method of heating and stirring while distilling H off may be used.

Of the above methods (A) and (B) for producing the nonionic surfactant of the present invention, the method (A) is preferred in the following respects. (A) The distribution of the number of moles added in the AO addition reaction tends to be narrow. (B) Easy rectification that may be performed if necessary [Rectification at the stage of polyoxyalkylene monoamine in production method (a) has a lower boiling point than rectification of the product by production method (b) Often].

The anionic surfactant of the present invention is, for example, a polyoxyalkylene glycol monoalkylamide wherein X in the general formula (1) is a hydrogen atom, and is represented by any of the general formulas (4) to (7). It can be obtained by introducing a group.

The introduction of the group represented by the general formula (4) can be carried out by a usual carboxyalkylation method.
For example, a method of reacting a monohalogenated alkyl carboxylic acid (alkyl group having 1 to 6 carbon atoms, preferably 1; monochloroacetic acid, monobromoacetic acid, etc.) in the presence of an alkali (such as sodium hydroxide), and in the presence of an alkali A method in which acrylonitrile or a lower alkyl acrylate (having 1 to 4 carbon atoms) ester is subjected to Michael addition followed by hydrolysis. In these cases, the equivalent ratio of the monohalogenated alkyl carboxylic acid, acrylonitrile or acrylic acid lower alkyl ester to the hydroxyl group is usually 0.1.
95 to 1.5 / hydroxyl group. The reaction temperature is usually 30
~ 120 ° C. The degree of anionization is usually at least 90 mol%, preferably at least 95 mol%.

The introduction of the group represented by the general formula (5) can be carried out by a usual sulfonation or sulfation method, for example, a method of reacting chlorosulfonic acid, sulfuric anhydride, sulfamic acid or sulfuric acid. Sulfuric anhydride is used after dilution with dry nitrogen or the like. In each case, the molar ratio of the sulfating agent is usually 0.95 to 1.03 / hydroxyl group, and the reaction temperature is 0 in the case of chlorosulfonic acid or sulfuric anhydride.
~ 70 ° C, 50 ~ 1 for sulfamic acid or sulfuric acid
50 ° C. The degree of anionization determined by measuring the amount of bound sulfuric acid is usually 90% mol or more, preferably 9%.
5 mol% or more.

The introduction of the group represented by the general formula (6) can be performed by a usual phosphorylation method, for example, a method of reacting with a phosphorylating agent such as phosphoric acid, polyphosphoric acid, phosphoric anhydride, phosphorus oxychloride and the like. . As an example, the reaction with phosphoric anhydride can be performed at a reaction temperature of 30 to 150 ° C. in a nitrogen atmosphere. When phosphoric anhydride is used, the molar ratio of phosphoric anhydride is usually 0.7 to 1.5 / hydroxyl group for the purpose of obtaining monophosphate as a main component. The degree of anionization determined by measuring the acid value of the product is usually at least 90 mol%, preferably at least 95 mol%.

The introduction of the group represented by the general formula (7) is carried out by a usual sulfosuccinic esterification method (method of maleation and sulfonation), for example, by reacting maleic anhydride with an alcohol without a catalyst in a non-aqueous system, Can be carried out by a method of producing a compound of maleic acid half ester and further reacting with sulfite or acid sulfite. The temperature of the half esterification reaction is usually 40 to 15
0 ° C., and the molar ratio of maleic anhydride is 0.9 to 1.1.
/ Is a hydroxyl group. The temperature of sulfonation is 40 to 100 ° C., and the equivalent ratio of sulfite or acid sulfite is 0.9 to 100.
1.5 / hydroxyl group. The degree of anionization determined by measuring the amount of bound sulfuric acid is usually at least 90 mol%, preferably at least 95 mol%.

The anionic surfactant of the present invention is characterized in that after the polyoxyalkylene glycol monoalkylamide other than the present invention is anionized, the reaction product is purified by a purification method such as rectification, extraction and recrystallization. It can also be obtained by a method. The preferred manufacturing method is a method of using a polyoxyalkylene glycol monoalkyl amides of the present invention as a raw material for anion, i.e., the general formula (1) most when the n of the weight percent of the major components is set to n _max n _max ± in _In this method, a polyoxyalkylene glycol monoalkylamide having a total of components in the range of ₁ or more of 80% by weight or more is anionized by the above method.

The nonionic surfactants and / or anionic surfactants of the present invention can be used in various applications, such as detergents,
When applied to thickeners, emulsifiers, dispersants, solubilizers, penetrants or wetting agents, etc., anionic surfactants other than the present invention, nonionic surfactants, cationic surfactants and / or An amphoteric surfactant may be used in combination. As these surfactants, those described in US Pat. No. 4,331,447 can be used.

Examples of the anionic surfactant other than the present invention include an ether carboxylic acid having a hydrocarbon group having 8 to 24 carbon atoms or a salt thereof [(poly) oxyethylene (degree of polymerization = 1 to 100) sodium lauryl ether acetate etc],
Sulfate or ether sulfate having a hydrocarbon group having 8 to 24 carbon atoms or a salt thereof [sodium lauryl sulfate, (poly) oxyethylene (degree of polymerization = 1)
To 100) sodium lauryl sulfate, (poly) oxyethylene (degree of polymerization = 1 to 100) triethanolamine lauryl sulfate, etc., sulfonate having a hydrocarbon group having 8 to 24 carbon atoms [sodium dodecylbenzene sulfonate, etc.] One or two hydrocarbon groups having 8 to 24 carbon atoms
Sulfosuccinate, phosphate or ether phosphate having a hydrocarbon group having 8 to 24 carbon atoms or a salt thereof [sodium lauryl phosphate,
(Poly) oxyethylene (degree of polymerization = 1 to 100) sodium lauryl ether phosphate], a fatty acid salt having a hydrocarbon group having 8 to 24 carbon atoms [sodium laurate, triethanolamine laurate, etc.] and a carbon number of 8 ~ 2
Acylated amino acid salts having a hydrocarbon group of 4 [sodium coconut fatty acid methyltaurine, coconut fatty acid sarcosine sodium, coconut fatty acid sarcosine triethanolamine, N-coconut fatty acid acyl-L-glutamate triethanolamine, N Coconut oil fatty acid acyl-sodium L-glutamate, sodium lauroylmethyl-β-alanine], and International Patent Publication WO 00/18.
Anionic surfactants described in the specification of 857 are exemplified.

The nonionic surfactants other than the present invention include, for example, aliphatic monohydric alcohols having 8 to 24 carbon atoms.
AO (2-8 carbon atoms) adduct (degree of polymerization = 1-100),
Polyhydric (2 to 10 or more) alcohol fatty acid (C8 to C24) ester [glycerin monostearate, sorbitan monolaurate, etc.], fatty acid (C8 to C24) alkanolamide [1: 1 type coconut] Oil fatty acid diethanolamide, 1: 1 type lauric acid diethanolamide, etc.], polyoxyalkylene (C2 to C8, degree of polymerization = 2 to 100) alkyl (C1 to C22) phenyl ether, (poly) oxyalkylene ( 2 carbon atoms
8, degree of polymerization = 1-100) alkyl (8-24 carbon atoms)
Amine and alkyl (C8-24) dialkyl (C1-6) amine oxides [lauryl dimethylamine oxide and the like], and International Patent Publication WO00 /
Non-ionic surfactants described in Japanese Patent No. 18857.

Examples of the cationic surfactant include quaternary ammonium salt type [stearyltrimethylammonium chloride, behenyltrimethylammonium chloride, distearyldimethylammonium chloride, aminopropylethyldimethylammonium ethyl sulfate lanolin fatty acid], amine salt type [ Stearic acid diethylaminoethylamide lactate, dilaurylamine hydrochloride, oleylamine lactate, etc.].

Examples of the amphoteric surfactant include betaine-type amphoteric surfactants [coconut oil fatty acid amidopropyldimethylaminoacetic acid betaine, lauryldimethylaminoacetic acid betaine, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine. , Laurylhydroxysulfobetaine, lauroylamidoethylhydroxyethylcarboxymethylbetaine sodium hydroxypropylphosphate, etc.), amino acid type amphoteric surfactant [β
-Sodium laurylaminopropionate].

The content of anionic surfactant in the total of all surfactants in the detergent, thickener, emulsifier, dispersant, solubilizer, penetrant or wetting agent of the present invention, the content of nonionic surfactant The content and the content of the cationic surfactant and / or the amphoteric surfactant are not particularly limited, but are preferably 3 to 80% by weight (% represents% by weight unless otherwise specified below) / 0 to 60%. % / 0-5
0%. Further, the content of the anionic surfactant of the present invention in the total of all the surfactants is preferably from 10 to 100%, more preferably from 15 to 100%. Further, the content of the anionic surfactant in the total of the anionic surfactant of the present invention and the nonionic surfactant of the present invention is preferably 30 to 100%, more preferably 40 to 100%. The content of the anionic surfactant of the present invention in the total anionic surfactant is preferably 30 to 100.
%, More preferably 40 to 100%.

Known auxiliary components can be added to the detergent, thickener, emulsifier, dispersant, solubilizer, penetrant or wetting agent of the present invention, if necessary. Such components include builders (zeolite, sodium carbonate,
Sodium sulfate, sodium tripolyphosphate, polycarboxylate, etc.), humectant (glycerin, sodium pyrrolidonecarboxylate, etc.), preservative [alkyl parabenzoate (carbon number 1)
5) esters, benzoic acid, dehydroacetic acid, etc.], antioxidants (2,6-di-t-butyl-p-cresol, butylated hydroxyanisole, triphenylphosphite, octylated diphenylamine, etc.), ultraviolet absorbers [2- (2′-hydroxy-5′-methylphenyl) benzotriazole, 2-hydroxy-4-methoxybenzophenone, etc.], chelating agents (sodium ethylenediaminetetraacetate, sodium polyphosphate, sodium metaphosphate, etc.), disinfectants ( Benzalkonium chloride, etc.), pH adjusters (mono and diethanolamine, caustic soda, lactic acid, citric acid, etc.), pigments (Additive Blue No. 1, Additive Red 2)
No. 4, food additive yellow No. 4, etc.), fragrances (limonene, phenylethyl alcohol, hexylcinnamic aldehyde, etc.),
Enzymes (protease, cellulase, etc.), optical brighteners and bleaching agents (sodium chlorite, etc.) are exemplified. The amount of the auxiliary component is not particularly limited, but in the case of a detergent, an enzyme,
The builder, chelating agent, fluorescent whitening agent and bleaching agent are each preferably 0.01 to 800 parts by weight based on 100 parts by weight of the anionic surfactant of the present invention. The humectants, preservatives, antioxidants, ultraviolet absorbers, bactericides, pH adjusters, pigments, and fragrances are each 0.1% by weight based on 100 parts by weight of the anionic surfactant of the present invention.
0001 to 500 parts by weight are preferred.

The anionic surfactants and / or nonionic surfactants of the present invention can be used in household detergents (such as clothing detergents, hair detergents, dish detergents, etc.) and industrial detergents (metals, precision parts). Etc.), emulsifiers (emulsifiers for emulsion polymerization, emulsifiers for agricultural chemical emulsions, emulsifiers for metalworking, emulsifiers for cosmetics, emulsifiers for water-based paints, etc.), dispersants (dispersion of paper chemicals such as pigments and fatty acid metal salts) Agent, dispersant for pesticide granules, dispersant for suspension polymerization, etc.), solubilizer (such as solubilizer for fragrance), foaming agent, penetrant, wetting agent, thickener, foaming agent, etc. It is.

When the anionic surfactant and / or nonionic surfactant of the present invention is used in clothing detergents or shampoos for household cleaning agents, the formulation is as follows:
For example, the following examples are given.

<Example of Formulation (Weight%) of Clothes Cleaning Agent> Anionic surfactant and / or nonionic surfactant of the present invention: 3 to 40% Anionic surfactant used in combination: 0 to 37% Nonionic surfactant: 5 to 20% Inorganic builder Zeolite: 10 to 30% Sodium silicate and sodium carbonate: 15 to 35% Sodium sulfate: 5 to 10% Organic builder Polycarboxylate, etc .: 2 to 10% Fluorescent brightening Preparation: 0-3% Enzyme: 0.2-2% Water: 1-10%

<Example of Shampoo Formulation (% by Weight)> Anionic surfactant and / or nonionic surfactant of the present invention: 3 to 20% Anionic surfactant used in combination: 0.7 to 20% Nonionic surfactant: 0 to 10% Humidifier (such as glycerin): 0.1 to 0.8% Thickener (such as coconut oil diethanolamide): 0.5 to 10% Chelating agent: appropriate amount Fragrance: appropriate amount preservative : Suitable amount of water: 60-92%

When the anionic surfactant and / or nonionic surfactant of the present invention is used as an emulsifier for emulsion polymerization, the monomers to be subjected to emulsion polymerization include the following known vinyl monomers. Can be

Vinyl hydrocarbons: aliphatic vinyl hydrocarbons [alkenes such as butene, isobutylene, pentene, heptene, diisobutylene, octene, dodecene, etc .; alkadienes such as butadiene, isoprene, etc.
1,4-pentadiene, 1,6-hexadiene, 1,7
-Octadiene, etc.], alicyclic vinyl hydrocarbons [(di)
Cyclopentadiene, vinylcyclohexene, etc.], aromatic vinyl hydrocarbons [styrenes such as styrene, α
-Methylstyrene, vinyltoluene, etc.],

Alkyl (meth) acrylate having an alkyl group having 1 to 50 carbon atoms [methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate , Dodecyl (meth) acrylate, etc.],

Carboxyl group-containing vinyl monomer and salt thereof: unsaturated monocarboxylic acid having 3 to 30 carbon atoms, unsaturated dicarboxylic acid and monoalkyl thereof (having 1 to 2 carbon atoms)
4) Esters [for example, (meth) acrylic acid, (anhydride) maleic acid, monoalkyl maleate, itaconic acid, etc.], as salts, for example, alkali metal salts (sodium salt, potassium salt, etc.), alkaline earth metal salts (Calcium salt, magnesium salt, etc.), ammonium salt, amine salt and quaternary ammonium salt.

Other monomers include a sulfone group-containing vinyl monomer, a hydroxyl group-containing vinyl monomer, a nitrogen-containing vinyl monomer, a quaternary ammonium cation group-containing vinyl monomer, a nitro group-containing vinyl monomer, and an epoxy group-containing monomer. Examples include vinyl monomers, halogen element-containing vinyl monomers, vinyl esters, vinyl (thio) ethers, vinyl ketones, and vinyl sulfones.

The method of emulsion polymerization using the anionic surfactant and / or the nonionic surfactant of the present invention is as follows.
There is no particular limitation, and conventionally known polymerization initiators and chain transfer agents can be used, and examples of the monomer concentration and the use of an emulsifier include the following. Monomer concentration: 30 to 50% by weight Emulsifier: Anionic surfactant and / or nonionic surfactant of the present invention 0.1 to 15% by weight / monomer Nonionic surfactant to be used in combination 0.2 to 10% by weight / monomer 0.1 to 5% by weight of anionic surfactant / monomer The anionic surfactant and / or nonionic surfactant of the present invention is not limited to the above-mentioned aqueous emulsion polymerization.
It can also be used as a suspension stabilizer for / O type suspension polymerization and non-aqueous suspension polymerization.

[0067]

EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Production Examples and Examples, but the present invention is not limited thereto. Unless indicated otherwise, parts indicate parts by weight and% indicates% by weight.

<Production Example of Nonionic Surfactant> Production Example 1 Monoethanolamine 12 was placed in a depressurizable glass reactor equipped with stirring, a temperature control function, a suspension tube and a cooling tube.
2 parts (2 mol) and 300 parts of methyl isobutyl ketone (3
Mol), and the mixture was refluxed and dewatered at 100 to 120 ° C. in a sealed state until the distillation of water ceased, and then unreacted methyl isobutyl ketone and distilled water were removed under reduced pressure. This reactant 2
86 parts (2 mol) were transferred to a stainless steel autoclave equipped with stirring and temperature control functions, and 0.08 part of aluminum perchlorate nonahydrate was charged thereinto. After the inside of the mixed system was replaced with nitrogen, the mixture was reduced under reduced pressure (20 mmHg). ), And dewatered at 120 ° C. for 1 hour. Next, 88 parts (2 moles) of EO were introduced at 110 ° C. so that the gauge pressure became 1 to 3 kgf / cm ² . Perform the aging reaction until the gauge pressure does not decrease,
After that, the catalyst removed by the adsorption treatment was transferred to a glass-made reaction vessel having a function of stirring and temperature control and capable of reducing pressure. 54 parts (3 mol) of water are charged and stirred at 120 ° C.
After hydrolysis, water and generated methyl isobutyl ketone were distilled off to obtain polyoxyethylene monoamine. The total of the components within the range of n ₂ ± ₁ was 83% (the measurement of the weight ratio of each n component was the same as the above measurement conditions). A glass-made reaction vessel capable of stirring and controlling the temperature and capable of reducing pressure was charged with 214 parts (1 mol) of lauric acid methyl ester and 116 parts of polyoxyethylene (nmax = 2) monoamine obtained by the above-mentioned reaction. The reaction was carried out at 150 to 160 ° C under a gas stream while distilling off methanol until no decrease in the total amine value was observed.
The remaining polyoxyethylene (nmax = 2) monoamine was distilled off to obtain a nonionic surfactant (A1).

Production Example 2 The polyoxyethylene monoamine obtained in Production Example 1 was rectified under reduced pressure (10 mmHg). As a result, a fraction having a total of 97% of components in the range of n ₂ ± ₁ was found to be 97%. 90-110
(The measurement of the weight ratio of each n component was the same as the above measurement conditions.) A nonionic surfactant (A2) was obtained in the same manner as in Production Example 1 except for using the fraction.

Production Example 3 Potassium hydroxide was used instead of aluminum perchlorate nonahydrate,
Polyoxyethylene monoamine was obtained in the same manner as in Production Example 1 except that 176 parts (4 mol) were used instead of EO 88 parts. When rectification was performed under reduced pressure (10 mmHg), a fraction having a total of 95% of components in the range of n ₃ ± ₁ was distilled at 120 to 140 ° C. (The weight ratio of each n component was measured. Same as the above measurement conditions). Further, instead of 214 parts of lauric acid methyl ester, 242 parts of myristic acid methyl ester, and 116 parts of polyoxyethylene (nmax = 2) monoamine, and polyoxyethylene (nmax =
3) Using 164 parts of the monoamine, the distillation temperature of the remaining polyoxyethylene (nmax = 3) monoamine was adjusted to 19
A nonionic surfactant (A3) was obtained in the same manner as in Production Example 1 except that the temperature was 0 to 200 ° C.

Production Example 4 A polyoxyethylene monoamine was obtained in the same manner as in Production Example 1 except that 264 parts (6 mol) were used instead of 88 parts of EO. When rectification was performed under reduced pressure (10 mmHg), a fraction having a total of 96% of components in the range of n ₄ ± ₁ was distilled at 160 to 180 ° C. (The weight ratio of each n component was measured. Same as the above measurement conditions). Further, instead of 214 parts of lauric acid methyl ester, 298 parts of isostearic acid methyl ester and 116 parts of polyoxyethylene (nmax = 2) monoamine were replaced with polyoxyethylene (nmax
= 4) Using 212 parts of monoamine, the distillation temperature of the remaining polyoxyethylene (nmax = 4) monoamine was adjusted to 2
A nonionic surfactant (A4) was obtained in the same manner as in Production Example 1 except that the temperature was changed to 10 to 230 ° C.

Production Example 5 Production Example 1 was repeated except that 150 parts (2 mol) of 2-hydroxypropylamine were used instead of 122 parts of monoethanolamine, and 116 parts (2 mol) of PO were used instead of 88 parts of EO.
In the same manner as in the above, polyoxypropylene monoamine was obtained.
After rectification under reduced pressure (10 mmHg), n ₂ ± ₁
Of which the total of the components within the range of 98% is 98%
Distillation was performed at 30 ° C. (the measurement of the weight ratio of each n component was the same as the above measurement conditions). Furthermore, polyoxyethylene (nm
x = 2) 146 parts of the above polyoxypropylene (nmax = 2) monoamine was used instead of 116 parts of the monoamine,
A nonionic surfactant (A5) was obtained in the same manner as in Production Example 1 except that the distillation temperature of the remaining polyoxypropylene (nmax = 2) monoamine was set at 210 to 230 ° C.

Comparative Production Example 1 In a glass container similar to that of Production Example 1, 214 parts (1 mol) of methyl laurate and 67 parts (1.1 mol) of monoethanolamine were charged and heated at 150 to 160 ° C. under a nitrogen stream.
The reaction was carried out while distilling off methanol until no decrease in the total amine value was observed.
At 0 ° C., the remaining monoethanolamine was distilled off.
The reaction product was transferred to a stainless steel autoclave equipped with stirring and temperature control functions, charged with 0.3 part of sodium hydroxide, and the mixture was purged with nitrogen.
(1 mol) at 150 ° C and a gauge pressure of 1-3 kgf / cm
^The resulting mixture was introduced so as to be ^2, and subjected to addition polymerization to obtain a nonionic surfactant (C1).

Comparative Production Example 2 Comparative production example except that 242 parts (1 mol) of myristic acid methyl ester was used instead of 214 parts of lauric acid methyl ester, and 88 parts (2 mol) was used instead of 44 parts (1 mol) of EO. In the same manner as in Example 1, a nonionic surfactant (C2) was obtained.

Comparative Production Example 3 Instead of 214 parts of lauric acid methyl ester, 298 parts (1 mol) of isostearic acid methyl ester and 44 parts of EO
A nonionic surfactant (C3) was obtained in the same manner as in Comparative Production Example 1, except that 132 parts (3 mol) was used instead of (1 mol).

The active ingredients of the nonionic surfactant were all 100%.

<Production Example of Anionic Surfactant> Production Example a The nonionic surfactant (A) obtained in Production Example 1 was placed in a glass container equipped with stirring, a temperature control function, and a dropping funnel.
1) 287 parts (1 mol) were charged, and 120 parts of chlorosulfonic acid (1.
03 mol) was added dropwise. After dehydrochlorination at the same temperature for 2 hours, the sulfate was neutralized with an aqueous solution obtained by dissolving 41.2 parts (1.03 mol) of sodium hydroxide in 890 parts of water to form an anionic interface containing 30% of the active ingredient. Activator (B1) was obtained.

Production Example b (A) obtained in Production Example 2 as a nonionic surfactant
Active ingredient 3 was prepared in the same manner as in Production Example a except that 2) was used.
0% of an anionic surfactant (B2) was obtained.

Production Example c The nonionic surfactant (A3) obtained in Production Example 3 was placed in a glass container equipped with stirring, a temperature control function, and a cooling tube.
359 parts (1 mol), sodium monochloroacetate 128
Parts (1.1 mol) and 300 parts of toluene, and while maintaining the temperature at 50 ° C., the degree of vacuum was set to 75 mmHg. Thereafter, 50 parts (1.25 mol) of granular sodium hydroxide were charged over 2 hours while dehydrating under reduced pressure, and the reaction was carried out for 6 hours. Thereafter, 330 parts of water was added, the mixture was acidified with hydrochloric acid, allowed to stand, separated, and subjected to toluene removal.
A solution prepared by dissolving 0 parts (1 mol) in 1010 parts of water is added.
An anionic surfactant (B3) having an active ingredient of 30% was obtained.

Production Example d The nonionic surfactant (A4) obtained in Production Example 4 was placed in a glass container equipped with stirring, a temperature control function, and a cooling tube.
459 parts (1 mol), maleic anhydride 108 parts (1.1
After reacting at 65 ° C. for 8 hours, a solution prepared by dissolving 151 parts (1.2 mol) of sodium sulfite in 1590 parts of water was added at 60 ° C. and reacted for 5 hours to obtain a sulfonated product. Thereafter, the pH was adjusted to 6.5 with citric acid, and the active ingredient 3 was added.
0% of an anionic surfactant (B4) was obtained.

Production Example e The procedure of Production Example a was repeated except that 287 parts of the nonionic surfactant (A1) was used instead of 287 parts of the nonionic surfactant (A1), and 960 parts of water was used instead of 930 parts of water. Thus, an anionic surfactant (B5) containing 30% of the active ingredient was obtained.

Comparative Production Example a In the same manner as in Production Example a except that the nonionic surfactant (C1) was used instead of the nonionic surfactant (A1),
An anionic surfactant (D1) having 30% of the active ingredient was obtained.

Comparative Production Example b The procedure of Production Example c was repeated except that the nonionic surfactant (C2) was used instead of the nonionic surfactant (A3).
An anionic surfactant (D2) having 30% of the active ingredient was obtained.

Comparative Production Example c The procedure of Production Example d was repeated, except that the nonionic surfactant (C3) was used instead of the nonionic surfactant (A4).
An anionic surfactant (D3) having 30% of the active ingredient was obtained.

Nonionic surfactants A1 to A5 and C
1 to C3, anionic surfactants B1 to B5 and D1
Table 1 shows the measurement results of the weight ratio of each of the n components of D3 to D3.

[0086]

[Table 1]

Examples 1 to 5 and Comparative Examples 1 to 3 <Foam stability test><Testmethod> Nonionic surfactants A1 to A5 and C1
To C3, castor oil and anionic surfactants other than the present invention were prepared in the following ratios of active ingredients to prepare sample solutions. Under the following conditions, the sample solution is 2,000 rpm with a home mixer.
After stirring at m, the mixture was allowed to stand, and the foam stability after 30 minutes was compared. Sample solution; Nonionic surfactants A1 to A5 or C1 to C3: 0.025% Polyoxyethylene (n = 2) sodium lauryl ether sulfate: 0.075% Castor oil: 0.05% Water: Remaining volume : 1000 mL Liquid temperature: 30 ° C Stirring time: 30 seconds <Evaluation method> The foam height immediately after stirring was stopped was set to acm, and the foam height 30 minutes after stopping stirring was set to bcm, and the foam stability was calculated by the following formula. did. Foam stability (%) = (ab) / a × 100 The evaluation results are shown in Table 2.

[0088]

[Table 2]

Examples 6 to 10 and Comparative Examples 4 to 6 <Evaluation of thickening and low-temperature stability><Evaluationmethod> Nonionic surfactants A1 to A5 and C1
To C3 and an anionic surfactant were prepared in the following ratios of the active ingredients to prepare sample solutions. The viscosity of the sample solution was measured under the following conditions, and the appearance at 5 ° C. was observed. <Viscosity measurement conditions> Measuring device: B-type rotational viscometer Sample solution; Polyoxyethylene (n = 2) sodium lauryl ether sulfate: 14% Nonionic surfactants A1 to A5 and C1 to C3: 6% Water: Remaining amount Liquid volume: 200 mL Liquid temperature: 25 ° C. <Evaluation criteria for thickening> Viscosity (unit: mPa) of the above compounded solution
・ S) was actually measured. <Evaluation criteria for low-temperature stability> The sample was allowed to stand at 5 ° C., and a period until the appearance began to become cloudy was observed. ：: 3 months or more ： １: 1 month or more and less than 3 months Δ: 1 week or more and less than 1 month ×: less than 1 week Table 3 shows the evaluation results of viscosity increase and low-temperature stability.

[0090]

[Table 3]

Examples 11 to 15 and Comparative Examples 7 to 9 <Test for Detergency><TestMethod> Anionic surfactants B1 to B5 and D1
Each aqueous solution containing 0.03% of the active ingredient of D3 was prepared and used as a sample solution. 7 pieces of JIS wet artificial contaminated cloth and JIS L
Ten test cloths (110 mm × 100 mm) specified by 0803 were prepared, and an artificially stained cloth was stapled on each of seven test cloths. Using 10 test cloths thus prepared, a detergency test was performed under the following conditions. Tester: Stirring type detergency tester (JIS K3362) Number of revolutions: 120 ± 5 rpm Liquid volume: 1000 ml Liquid temperature: 30 ° C. Time: Cleaning 10 minutes Rinse 3 minutes × 2 times (tap water) After testing, artificial after cleaning The contaminated cloth was air dried. <Evaluation Method> The reflectance (540 nm) of the washed artificially stained cloth, the unwashed artificially stained cloth and the clean cloth was measured, and the detergency was calculated by the following equation. Detergency (%) = {(Rw−Rs) / (RI−Rs)} ×
100 RI: reflectivity of the clean cloth Rw: reflectivity of the artificially stained cloth after washing Rs: reflectance of the unstained artificially stained cloth A multi-source spectrophotometer (manufactured by Suga Test Instruments) was used to measure the reflectivity. . Table 4 shows the evaluation results.

[0092]

[Table 4]

Examples 16 to 20 and Comparative Examples 10 to 12 Anionic surfactants B1 to B4 and D1 to D3, and nonionic surfactants (A1) to (A5) and (C1) to (C3) Prepared as a hair cleanser (shampoo) according to the formulation (active ingredient indication) shown in Table 5,
Usability was evaluated. <Evaluation method>"Foaming","foamquality", and "texture" at the time of use by panelists of 10 men and women were judged according to the following five-grade criteria, and the total score was evaluated. Table 6 shows the evaluation results. <Evaluation Criteria>"Bubble"; Bubble very well 5 points Bubble very well 4 points Bubble normally 3 points Bubble less 2 points Almost no bubbling 1 point "Foam quality"; Fine creamy bubbles 5 points Slightly fine bubbles 4 points Normal Bubble of size 3 points Slightly rough bubbles 2 points Very rough bubbles 1 point "Hand" Very smooth finger passage 5 points Very smooth finger passage 4 points Normal finger passage 3 points Finger passage slightly heavy 2 points Finger The street is bad and it gets stuck 1 point

[0094]

[Table 5]

[0095]

[Table 6]

[0096]

The nonionic surfactant and the anionic surfactant of the present invention have a high stability over time when blended in a detergent composition, and their appearance is not blurred even at a low temperature. In addition, because it shows excellent detergency, compoundability, foaming power, usability, thickening, foam stability, etc., it is used for household detergents (clothing detergents, hair detergents, dish detergents, etc.) and industrial detergents. It is suitable as a wide range of cleaning agents such as agents (such as cleaning agents for metals and precision parts). In addition, it has excellent emulsifying properties, dispersing properties, penetrating properties, wettability and the like. Dispersants (eg, dispersants for paper chemicals such as pigments and fatty acid metal salts, dispersants for pesticide granules, and dispersants for suspension polymerization), solubilizers (such as solubilizers for flavors), and penetrants. It is also useful as a wetting agent.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI theme coat ゛ (Reference) C11D 1/28 C11D 1/28 1/29 1/29 1/34 1/34 3/386 3/386 3 / 395 3/395 3/40 3/40 3/48 3/48 3/50 3/50 // A61K 7/075 A61K 7/075 F term (reference) 4C083 AC122 AC642 AD041 AD042 AD071 AD072 BB04 BB05 4D077 AB03 AB10 AB11 AB14 AB17 AC01 AC05 AC06 AC07 BA13 BA15 DC02Y DC19Y DC26Y DC48Y DC59Y DD32Y DD33Y 4H003 AB06 AB23 AB34 AB39 AC13 AD04 DA01 DA02 DA09 DA17 EA12 EA15 EA28 EB05 EB42 EC01 ED02 FA07 FA12 FA26 FA28 FA30 FA01 FA04 A37 FA04 BB17 BB19 DH03

Claims (6)

[Claims] 1. A represented by the general formula (1), different n a surfactant comprising a component having a, in the range of n _max ± ₁ when the n most weight percent of more components as n _max A nonionic or anionic surfactant having a total of components of 80% by weight or more. R ¹ -CONH- (AO) _n -X (1) [wherein, R ¹ is a hydrocarbon group having 7 to 24 carbon atoms, X is a hydrogen atom or an anionic group, and A is one type having 2 to 5 carbon atoms. The above alkylene group and n represent an integer of 1 or more with an average of 1.5 to 20. ] 2. A compound comprising an amide-forming compound represented by the following general formula (2) and a component represented by the following general formula (3) having different n, and Is obtained by reaction with a polyoxyalkylene monoamine in which the total of components within the range of n _max ± ₁ is 80% by weight or more, where n _max is n _max.
The nonionic surfactant according to the above. R ¹ -CO-Z (2) [wherein, R ¹ represents a hydrocarbon group having 7 to 24 carbon atoms, Z represents a hydroxyl group, OR ² or a halogen atom. Where R ²
Represents an alkyl group having 1 to 6 carbon atoms. _{] H 2 N- (AO) n} -H (3) [ In the formula, A 1 or more alkylene groups having 2 to 5 carbon atoms,
n represents an integer of 1 or more with an average of 1.5 to 20. ] 3. The anionic surfactant according to claim 1, wherein Z is any of the following formulas (4) to (7). -(CH ₂ ) _p CH ₂ COOM _{1 / r} (4)-(CH ₂ ) _p SO ₃ M _{1 / r} (5) Embedded image Wherein p is 0 or an integer of 1 to 5, and one of L is SO ₃
At M _{1 / r} , the other is a hydrogen atom. M represents a hydrogen atom or a r-valent cation, and r is 1 or 2. ] 4. The anionic surfactant according to claim 3, which is obtained by further anionizing the nonionic surfactant according to claim 2. 5. A detergent, a thickener, an emulsifier, a dispersant, a solubilizer, a penetrant or a wetting agent containing the surfactant according to claim 1. 6. Other anionic surfactants, other nonionic surfactants, amphoteric surfactants, cationic surfactants, builders, humectants, preservatives, antioxidants, ultraviolet absorbers, chelating agents The detergent, thickener, emulsifier, dispersant, and solubilizer according to claim 5, comprising one or more selected from the group consisting of a bactericide, a pH adjuster, a pigment, a fragrance, an enzyme, and a bleaching agent. , Penetrants or wetting agents.