JPH0920740A - Polyoxypropylene fatty acid isopropanolamide mixture, its production and chemical containing the same mixture - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject mixture having excellent thickening property, foam-increasing property and foaming stability as well as low melting point and good handling property, excellent in low-temperature stability, etc., in blending and useful for thickening agent, emulsifier, forming stabilizer, cosmetic, detergent, etc. SOLUTION: This polyoxypropylene fatty acid isopropanolamide mixture comprises a mixture of two or more kinds of compounds expressed by formula I [R is a 7-21C straight-chain or branched unsaturated hydrocarbon; PO is a 3C oxyalkylene; (m) is an integer of 0 or >=1] in which average value of (m) of the compound expressed by formula I is a positive number of 0.3-20, e.g. polyoxypropylene lauric acid isopropanolamide mixture. The compound of formula I is obtained by reacting a fatty acid alkylester of formula II (R<1> is a 1-3C alkyl) with isopropanolamine of formula III in the presence of a base catalyst to prepare a reaction mixture containing an aliphatic isopropanolamide of formula IV and directly carrying out addition reaction of the compound of formula IV with propylene oxide in an amount of 0.3-20 times by mol based on 1mol of the compound of formula IV.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a specific polyoxypropylene fatty acid isopropanolamide mixture, a method for producing the same, and various chemical agents containing the compound mixture. The chemical agent is a thickener, a foaming agent, a foam stabilizer, an emulsifier, a dispersant, a solubilizer, a cosmetic having good emulsion stability and a feeling of use, and a foaming power / detergency / foaming power. It includes a detergent composition having excellent foam stability, thickening property, and low temperature stability, and less irritation to skin, hair, and eye mucous membranes.

[0002]

2. Description of the Related Art In general, detergents such as shampoos and body shampoos tend to be required to exhibit rich foaming and excellent detergency. Therefore, a foaming agent that acts as a foaming stabilizer is added to the surfactant that is the main base. In addition, since many of the surfactant components used as the main base have a relatively low viscosity, it is common to add a thickening agent to adjust the viscosity of the product so that it can be easily handled, depending on the application. Has been done.

Conventionally, fatty acid alkanolamides such as fatty acid monoethanolamide, fatty acid isopropanolamide, and fatty acid diethanolamide and polyoxyethylene fatty acid monoethanolamide have been used as thickeners, foaming agents, and foam stabilizers. It was preferred because it has less irritation to the skin and hair. However, although fatty acid monoethanolamide and fatty acid isopropanolamide are extremely excellent in the foam increasing action, they have a drawback that they have a high melting point and therefore have poor solubility when they are incorporated into detergents and cosmetics. Was. In particular, when the compounding amount is large, it causes turbidity and dullness when stored at low temperature, and the amount used, product form, and application are limited. Also, the foaming stability was not satisfactory. Furthermore, the fatty acid monoethanolamide has a slight ocular mucous membrane stimulating property, and has a drawback in that when a compounded shampoo composition or the like is put into the eyes, the eyes become dull.

Since fatty acid diethanolamide has a lower melting point than fatty acid monoethanolamide and fatty acid isopropanolamide, it is excellent in handling property and solubility at the time of compounding. Further, although its thickening property is inferior to that of fatty acid monoethanolamide, it is easy to adjust to an appropriate viscosity, and due to this advantage, it has been favorably used in shampoos and body shampoos. However, the fatty acid diethanolamide is more susceptible to hydrolysis of the amide group than the fatty acid monoethanolamide or the fatty acid isopropanolamide, and therefore the stability of the compound itself is poor, and
It has a drawback of poor stability in a relatively high pH region of pH 9 or higher, and is therefore unsuitable for compounding into a high pH system. In addition to the above fatty acid alkanolamides, polyoxyethylene (2 to 10) fatty acid monoethanolamides and the like are widely used for improving foaming stability.
However, although these are excellent in foaming stability, they have a drawback that they are not sufficient in thickening property and foaming property. Furthermore, polyoxyethylene (2 to 10) fatty acid monoethanolamide is said to produce a small amount of toxic dioxane as a by-product due to the polymerization of ethylene oxide itself in the production process thereof, that is, when ethylene oxide is added to fatty acid monoethanolamide. I have a problem.
Therefore, after the addition of ethylene oxide, a step of removing dioxane from the reaction product is required, and there is a drawback that the manufacturing process becomes complicated.

Generally, in cosmetics such as cream,
In order to uniformly emulsify, disperse or solubilize the blended components, higher alcohols, fatty acid esters and the like are used. However, depending on the blending composition, the stability of the emulsion or dispersion is poor and it may separate during long-term storage. Further, there is a drawback that the usability is not sufficiently satisfactory. Further, as a general emulsifier, fatty acid soap, fatty acid glyceride, sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene polyoxypropylene block polymer, etc. are used. . However, these conventional emulsifiers
Its emulsifying power is not fully satisfactory. Emulsifiers containing ester groups are particularly susceptible to hydrolysis, so
As a result, there is a problem in that the emulsion system collapses during long-term storage, and phenomena such as oil-off occur.

[0006] Generally, as the dispersant, an anionic surfactant having a sulfate group or a sulfonic acid group,
Various metal soaps such as stearic acid soap, nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene fatty acid ester, and sorbitan fatty acid ester are used. However, the dispersibility of these conventional dispersants has not been sufficiently satisfactory. Furthermore, as the solubilizing agent, polyoxyethylene alkyl ether, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene castor oil, polyoxyethylene hydrogenated castor oil, sucrose fatty acid monoester, etc. are used. However, these conventional solubilizers are not sufficiently satisfactory in solubilizing power, and particularly when an ester-based solubilizer is used, the solubilized substance may be liberated over time. .

Under the above circumstances, there is a demand for a thickener, a foaming agent and a foaming stabilizer which are excellent in solubility, handleability, stability and non-irritating property. It was There has also been a demand for an emulsifier, a dispersant and a solubilizer which are stable over time. In addition, a method for producing them industrially easily and safely has been desired. Furthermore, cosmetics with good emulsion stability and excellent usability, and excellent foaming power, detergency, foaming stability, thickening and low temperature stability, stable in a wide pH range, There has been a need for a detergent composition that does not irritate hair and eye mucous membranes.

Regarding polyoxyalkylene fatty acid alkanolamides, JP-A-60-49099, 63-
189499, 63-196697, JP-A 2-1
No. 51692 and Japanese Patent Publication No. 2-504165, but there is no description of a fatty acid alkanolamide to which propylene oxide or ethylene oxide is added. Also, JP-A-53-54208
Nos. 54-15911, 59-210999, 60-96695 and the like describe ethylene oxide adducts of fatty acid monoethanolamides or fatty acid diethanolamides, but regarding propylene oxide adducts of fatty acid isopropanolamides. There is no description.

Further, JP-A-61-161625 and 61-1
14727, 61-227830, 61-2278.
32, 61-246296, 62-57491,
No. 62-209200 describes alkylene oxide adducts of fatty acid alkanolamides, but both are block or random adducts of ethylene oxide and propylene oxide, and the total number of added moles is 13 times or more. It is a large one and is used only as a non-aqueous solid dispersant or a non-aqueous cleaning agent.

JP-A-61-114727 describes polyoxypropylene fatty acid monoethanolamide, which is an invention of a non-aqueous solid dispersant,
No mention is made of the effect as a cosmetic or a detergent used in the water system of the present invention.

[0011]

DISCLOSURE OF THE INVENTION The present invention provides a specific polyfunctional compound useful for chemical applications such as thickeners, foaming agents, foam stabilizers, emulsifiers, dispersants, solubilizers, cosmetics and detergents. Oxypropylene fatty acid isopropanolamide mixture, its industrially easy production method and chemical agent containing the specific polyoxypropylene fatty acid isopropanolamide mixture, namely, thickener, foaming agent, foam stabilizer, emulsifier,
Dispersants, solubilizers, cosmetics with good emulsion stability and excellent usability, and excellent foaming power, detergency, foaming stability and thickening properties, stable in a wide pH range, and easy to handle. It is intended to provide a detergent composition which is easy and has good solubility, has good low-temperature stability at the time of formulation, has little irritation to the skin, hair and eye mucous membranes and is excellent in safety.

[0012]

The present inventors have taken advantage of the characteristics of fatty acid alkanolamides, which are typical thickeners, foaming agents and foaming stabilizers, while maintaining instability and handling properties at high pH. As a result of intensive research to improve problems such as poor mixing and stability at low temperature during compounding, a polyoxypropylene fatty acid isopropanolamide mixture having a specific number of added moles has excellent thickening property, foaming property and foaming property. It is stable and has a low melting point, so it is easy to handle, stable in a wide pH range, and has minimal irritation to the skin, hair, and eye mucous membranes. For example, foaming power, cleaning power,
It has been found that a detergent composition having improved foaming stability and thickening property, excellent stability at low temperature at the time of compounding, almost no irritation to skin and hair, and excellent safety can be obtained.
Even more surprisingly, the mixture of specific polyoxypropylene fatty acid isopropanolamide is also excellent in emulsifying power, dispersing power and solubilizing power, and when it is used in cosmetics, the emulsion stability is improved and the feeling of use is improved. I also found it to be excellent. The present invention has been completed based on the above findings.

That is, the polyoxypropylene fatty acid isopropanolamide mixture of the present invention has the following general formula (I):

Embedded image (However, in the formula (I), R represents a linear or branched saturated hydrocarbon or unsaturated hydrocarbon group having 7 to 21 carbon atoms, and PO
Represents an oxyalkylene group having 3 carbon atoms, and m is 0 or 1.
A mixture of two or more compounds represented by the above formula, wherein m of the compound of formula (I) in this mixture is
The average value of is a positive number of 0.3 to 20.

The method for producing a mixture of polyoxypropylene fatty acid isopropanolamides of the above formula (I) according to the present invention is represented by the following general formula (II):

[Chemical 6] (In the formula (II), R is the same as the above, and R ¹ has ¹ carbon atom.
Represents an alkyl group of 1 to 3. ) A fatty acid alkyl ester represented by the formula (III):

Embedded image Is reacted with isopropanolamine represented by the formula (IV):

Embedded image (Wherein R is the same as the above in the formula (IV)), a reaction mixture containing a fatty acid isopropanolamide represented by the formula (IV) contained in the reaction mixture without purification of the reaction mixture is prepared. To the compound of 0.3
It is characterized in that an addition reaction is carried out with ˜20 times mole of propylene oxide.

The thickener of the present invention is characterized in that it contains the polyoxypropylene fatty acid isopropanolamide mixture of the above formula (I).

The foam booster of the present invention is characterized by containing a mixture of polyoxypropylene fatty acid isopropanolamides of the above formula (I).

The foam stabilizer of the present invention is characterized by containing the polyoxypropylene fatty acid isopropanolamide mixture of the above formula (I).

The emulsifier of the present invention is characterized in that it contains the polyoxypropylene fatty acid isopropanolamide mixture of the above formula (I).

The dispersant of the present invention is characterized in that it contains the polyoxypropylene fatty acid isopropanolamide mixture of the above formula (I).

The solubilizer of the present invention is characterized by containing the polyoxypropylene fatty acid isopropanolamide mixture of the above formula (I).

The cosmetic material of the present invention is characterized by containing the polyoxypropylene fatty acid isopropanolamide mixture of the above formula (I).

The detergent of the present invention is characterized in that it contains the polyoxypropylene fatty acid isopropanolamide mixture of the above formula (I).

The detergent composition of the present invention is selected from the polyoxypropylene fatty acid isopropanolamide mixture of the above formula (I) and an anionic surfactant, a cationic surfactant, an amphoteric surfactant and a nonionic surfactant. It is characterized by containing at least one kind.

[0024]

The polyoxypropylene fatty acid isopropanolamide of the formula (I) contained in the mixture of the present invention is as follows. In the following compound names, the number in parentheses is the number of moles of propylene oxide subjected to the addition reaction with respect to 1 mole of fatty acid isopropanolamide. Polyoxypropylene (0.3) lauric acid isopropanolamide, polyoxypropylene (0.5) lauric acid isopropanolamide, polyoxypropylene (1) lauric acid isopropanolamide, polyoxypropylene (1.5) lauric acid isopropanolamide, Polyoxypropylene (2) lauric acid isopropanolamide, polyoxypropylene (5) lauric acid isopropanolamide, polyoxypropylene (10) lauric acid isopropanolamide, polyoxypropylene (20) lauric acid isopropanolamide, polyoxypropylene (1. 5) Capric acid isopropanolamide, polyoxypropylene (1.5) decanoic acid isopropanolamide, polyoxypropylene (1.5) myristic acid a Propanol amide, polyoxypropylene (1.5) palmitic acid isopropanolamide, polyoxypropylene (1.
5) stearic acid isopropanolamide, polyoxypropylene (1.5) isostearic acid isopropanolamide, polyoxypropylene (1.5) oleic acid isopropanolamide, polyoxypropylene (1.
5) Coconut oil fatty acid isopropanolamide, polyoxypropylene (1.5) beef tallow fatty acid isopropanolamide, polyoxypropylene (1.5) Soybean oil fatty acid isopropanolamide, polyoxypropylene (1.5)
Palm kernel oil fatty acid isopropanolamide etc. can be mentioned.

The number of moles of propylene oxide (PO) added in the compound of formula (I) contained in the polyoxypropylene fatty acid isopropanolamide mixture of the present invention is m.
Is an integer of 0 or 1 or more, and its average value, that is, the average number of added moles is 0.3 to 20. If the average number of added moles is less than 0.3, the melting point of the resulting mixture becomes excessively high, resulting in poor handleability and poor solubility. However, when it exceeds 20, the thickening property, the foaming property, the foaming stability, the emulsifying property, the dispersibility, and the solubilizing property of the resulting mixture are rapidly lowered. In the average addition mole number range of propylene oxide of 0.3 to 20, the smaller the average addition mole number, the better the thickening property, the foam increasing property, the emulsifying property, and the solubilizing property. The number is preferably 0.3-2. On the other hand, with respect to foaming stability and dispersibility, it is preferable that the average addition mole number is large, and specifically, the addition mole number m is preferably 2 to 20.

The method for producing a mixture of polyoxypropylene fatty acid isopropanolamide represented by the general formula (I) will be described in detail below. The polyoxypropylene fatty acid isopropanolamide mixture of the present invention is produced by adding propylene oxide to fatty acid isopropanolamide. Specific examples of the fatty acid isopropanolamide used here include capric acid isopropanolamide, decanoic acid isopropanolamide, lauric acid isopropanolamide, myristic acid isopropanolamide, palmitic acid isopropanolamide, stearic acid isopropanolamide, isostearic acid isopropanolamide, 2-octyldecanoic acid isopropanolamide, 2-heptylundecanoic acid isopropanolamide, oleic acid isopropanolamide, linoleic acid isopropanolamide, linolenic acid isopropanolamide, coconut oil fatty acid isopropanolamide, palm kernel oil fatty acid isopropanolamide,
Soybean oil fatty acid isopropanolamide, tallow fatty acid isopropanolamide and the like can be mentioned. These fatty acid isopropanolamides may be used alone or as a mixture of two or more kinds.

The method for adding propylene oxide to fatty acid isopropanolamide is not particularly limited. For example, in the presence of a Lewis acid catalyst such as boron trifluoride, titanium chloride or tin chloride, or a base catalyst such as sodium hydroxide, potassium hydroxide, sodium methoxide or sodium ethoxide, propylene oxide is converted into the above alkanolamide compound. Can be reacted.
This reaction requires the presence of either of these catalysts, and the addition reaction does not proceed or is very slow with highly purified fatty acid isopropanolamide.

The temperature of the propylene oxide addition reaction is
It may be higher than the melting point of the fatty acid isopropanolamide, but is preferably 80 to 180 ° C. If the temperature is lower than 80 ° C, the reaction is slow, and if the temperature is higher than 180 ° C, the coloring may be remarkable, which is not preferable. In order to prevent or suppress coloring, it is effective to replace the air in the reactor with an inert gas in advance. As a method for charging propylene oxide, (a) charging before heating, (b)
Any method may be used, such as heating to the reaction temperature and then pressurizing in a liquid state, or (c) heating to the reaction temperature and then blowing in a gas state. However, since heat is generated during the addition reaction, temperature control may be difficult with the method (a). Therefore, it is preferable to employ the method (b) or (c), which is easy to suppress the temperature, in the case of mass production.

After the completion of the propylene oxide addition reaction, the obtained polyoxypropylene fatty acid isopropanolamide can be directly used in the next step without purification. In general, like polyoxyethylene fatty acid alkanolamides, fatty acid alkanolamides with ethylene oxide added contain a small amount of toxic dioxane, so a step of removing this dioxane is required, but the present invention product Does not require a dioxane removal step since it does not use ethylene oxide. However, when it is necessary to avoid the presence of a trace amount of dissolved propylene oxide, the dissolved propylene oxide can be easily removed by lightly reducing the pressure of the reaction mixture.

If it is necessary to avoid the remaining catalyst used, the following treatment may be performed. That is,
When a Lewis acid is used as a catalyst, water is added in an amount of 1 to 100 times the amount of the catalyst used in the reaction mixture to quench, and then the Lewis acid is removed under reduced pressure. When a base catalyst is used, it may be neutralized with a mineral acid such as hydrochloric acid or sulfuric acid or an organic acid such as acetic acid. However, when the inorganic salt or organic salt formed at this time is also repelled, it can be easily removed by a method such as filtration.

In the propylene oxide addition reaction, a solvent may be used as long as it does not hinder the reaction. Examples of the solvent that can be used include hydrocarbon solvents such as hexane, benzene, toluene, and xylene, halogen solvents such as chloroform and dichloroethane, and ether solvents such as tetrahydrofuran, diisopropyl ether, and dibutyl ether. You can When these solvents are used, the solvent may be removed by distillation under reduced pressure after the completion of the propylene oxide addition reaction.

To synthesize fatty acid isopropanolamide, (1) a method of dehydrating and condensing a fatty acid and isopropanolamine, (2) a method of reacting a fatty acid halide with isopropanolamine, and (3) a lower alcohol ester of fatty acid and isopropanolamine A method of reacting while removing lower alcohol can be used. In the method (1), it is difficult to obtain a high-purity fatty acid isopropanolamide because it is difficult to complete the reaction, some unreacted raw material remains, and impurities such as amide ester and amine ester are by-produced. Some of these impurities include those that are more susceptible to the addition reaction of propylene oxide than fatty acid isopropanolamide, and if you try to add propylene oxide with these impurities included, the addition reaction of propylene oxide to impurities will also occur. As it progresses, the obtained polyoxypropylene fatty acid isopropanolamide has a drawback that the purity is further lowered. Further, since the reaction temperature must be higher than that of other methods, there is a drawback that coloring is intense.

In the above method (2), hydrogen chloride is generated, so that a reagent or a device for trapping the hydrogen chloride is required, and the problem of corrosion of the device and the fatty acid halide are relatively expensive, which is an industrially excellent method. It is hard to say. In order to obtain the polyoxypropylene fatty acid isopropanolamide of the present invention, the method (3) above in which the obtained fatty acid isopropanolamide has a high purity is preferable. A base catalyst is used in the method (3). As mentioned above, a catalyst is required for the propylene oxide addition in the next step,
When the fatty acid isopropanolamide is produced by the method (3), its base catalyst is also effective as a catalyst for the propylene oxide addition reaction, and therefore a catalyst essential for this addition reaction is added at the stage of adding propylene oxide. This is a very efficient method as it eliminates the need.

The method for producing the polyoxypropylene fatty acid isopropanolamide mixture of the present invention most efficiently is as follows. That is, a raw material consisting of a fatty acid lower alcohol ester, isopropanolamine and a base catalyst is heated, and a condensation reaction is carried out while distilling off the generated lower alcohol to prepare a fatty acid isopropanolamide. Next, this fatty acid isopropanolamide is subjected to an addition reaction of propylene oxide.

An example of the actual situation of this reaction is as follows.

Embedded image

The fatty acid alkyl ester represented by the general formula (II) used in the method of the present invention is, for example, capric acid, decanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, linoleic acid. , Linolenic acid, coconut oil fatty acid, beef tallow fatty acid, palm kernel oil fatty acid and other methyl esters, ethyl esters, propyl esters, isopropyl esters and the like.

The molar ratio of the isopropanolamine represented by the general formula (III) and the fatty acid alkyl ester used in the method of the present invention is preferably (isopropanolamine) / (fatty acid lower alkyl ester) = 0.8 to 1.2. , 1.0 to 1.1 are more preferable, and 1.02 to 1.0
8 is more preferred.

The base catalyst used in the method of the present invention includes metal alkoxides such as sodium methoxide and sodium ethoxide, and sodium hydroxide.
Examples thereof include metal hydroxides such as potassium hydroxide.
The amount used is preferably 0.01 to 5 mol% with respect to the fatty acid alkyl ester represented by the general formula (II),
5 to 2 mol% is more preferable.

The reaction temperature for the amidation is 50 to 180 ° C.
And a reaction time of up to 24 hours is sufficient. Since the lower alcohol produced by the amidation reaction is distilled off, the pressure is preferably controlled within the range of 0.1 to 760 mmHg, more preferably within the range of 10 to 50 mmHg. However, at this time, it is desirable to set the pressure while looking at the relationship with the temperature so that the reaction temperature does not exceed the boiling points of the acid lower alcohol ester and isopropanolamine.

Since this amidation reaction proceeds almost quantitatively, the obtained fatty acid isopropanolamide reaction mixture containing a base catalyst can be directly used for the next propylene oxide addition reaction without purification. The propylene oxide addition reaction may be carried out by the above method. However, in general, many fatty acid isopropanolamides solidify when cooled, so a method of adjusting the temperature of the reaction solution to a desired propylene oxide addition temperature and charging propylene oxide in a liquid or gaseous state, that is, the above-mentioned (b) The methods of (c) to (c) are efficient.

After the addition of propylene oxide, if there is a problem with the base catalyst used as the reaction catalyst, the reaction mixture is neutralized with an acidic substance such as hydrochloric acid, sulfuric acid, sulfurous acid or sulfurous acid gas to form a salt. It may be removed by filtration. In addition, when a small amount of unreacted propylene oxide dissolved in the reaction solution is to be repelled after the addition of propylene oxide, the residual propylene oxide can be easily removed by lightly reducing the pressure inside the reaction vessel.

The polyoxypropylene fatty acid isopropanolamide mixture represented by the general formula (I) of the present invention is
Even by itself, it has surface activity. However, when it is used alone, the foaming power and the cleaning power are not always sufficient. However, when combined with other surfactants, the performance of the other surfactants can be enhanced. The performance that can be enhanced by blending the polyoxypropylene fatty acid isopropanolamide mixture of the present invention includes a thickening effect (thickening agent), a foaming power enhancing effect (foaming agent), and a long-lasting foam stabilizing effect ( Foam stabilizer) etc.

The polyoxypropylene fatty acid isopropanolamide mixture represented by the general formula (I) of the present invention is
Not only does it have excellent performance as a thickener, foam booster, and foam stabilizer, but it also has little irritation to the skin, hair, and eye mucous membranes, is excellent in handling and solubility, and has a wide range of properties.
It has the characteristic that it is difficult to hydrolyze even at pH. Therefore, as compared with conventional thickeners such as fatty acid alkanolamides and polyoxyethylene fatty acid alkanolamides, foaming agents, foam stabilizers, thickeners comprising the polyoxypropylene fatty acid isopropanolamide mixture of the present invention, The foam boosters and foam stabilizers can be applied to a wider range of fields and various product forms.
Furthermore, the polyoxypropylene fatty acid isopropanolamide mixture of the present invention is also excellent in emulsifying power, dispersing power, and solubilizing power, and because of its good solubility and hardly decomposing property, cosmetics, detergents, fibers, foods, agricultural chemicals. It can be used as an excellent emulsifier, dispersant and solubilizer in various fields such as paints, paints and polymers.

The general formula (I) used in the cosmetics of the present invention
The content of the polyoxypropylene fatty acid isopropanolamide mixture represented by
-20% by weight is preferable, and 1-5% by weight is more preferable. If the content in the cosmetic is less than 0.1% by weight, the effect may be insufficient, and if it exceeds 20% by weight, the emulsion stability of the obtained cosmetic may be deteriorated, resulting in stickiness during use. The feeling may become strong, which is not preferable. In the cosmetics of the present invention, as an oil agent, higher alcohols such as cetyl alcohol, stearyl alcohol and behenyl alcohol, higher alcohol ethers such as cetyl alcohol polyglycol ether, higher fatty acids such as stearic acid, higher fatty acids such as triethanolamine stearate. Salts, fatty acid esters such as glyceryl stearate, isopropyl palmitate and the like can be used.

The cosmetics of the present invention may contain polyhydric alcohols such as glycerin, propylene glycol, 1,3-butylene glycol and sorbitol, lanolins, polyacrylic acid polymers, hyaluronic acid, carboxymethyl chitin, if necessary. Water-soluble polymeric substances such as elastin, chondroitin sulfate, dermatanic acid, fibronectin, and ceramides, cell activating agents such as aloe extract and placenta extract, allantoin, anti-inflammatory agents such as glycyrrhizinate, edetate, citric acid, apple Acid, chelating agent such as gluconic acid, benzoate, salicylate, sorbate, dehydroacetate, paraoxybenzoate, 2,
Preservatives such as 4,4'-trichloro-2'-hydroxydiphenyl ether, 3,4,4'-trichlorocarbanilide, benzalkonium chloride, hinokitiol, resorcin, fungicides, dibutylhydroxytoluene, butylhydroxyanisole, gallic Antioxidants such as propyl acid, ascorbic acid, oxybenzone, 4-tert
UV absorbers such as -butyl-4'-methoxybenzoylmethane and 2-ethylhexylparadimethylaminobenzoate, silicone compounds such as amino-modified silicone and polyether-modified silicone, and fragrances and dyes can be appropriately used.

The shape of the cosmetic of the present invention is not limited, and it may be in any state such as a solubilized system, an emulsified system, a powder dispersion system, a water-oil two-layer system. In order to produce the cosmetic of the present invention, the required components may be blended and mixed by a blending method generally used by those skilled in the art. Further, the use of the cosmetic of the present invention is also optional, but as a typical example, skin cosmetics such as lotion, emulsion, cream, pack, cleansing, beauty essence, foundation, and rinse, hair treatment, hair conditioner. , Hair brushing agents, hair tonics, permanent wave agents, hair decolorizing agents, hair cosmetics such as hair dyes, makeup soaps, bath agents and the like.

The content of the polyoxypropylene fatty acid isopropanolamide mixture represented by the general formula (I) used in the detergent composition of the present invention is not particularly limited,
0.1 to 20% by weight is preferable, more preferably 1 to 5
% By weight. If it is less than 0.1% by weight, the effect may be insufficient, and if it exceeds 20% by weight, the foaming power, detergency and viscosity increase may be rather reduced, and the stickiness during use may be strong. May occur, which is not preferable.

As the anionic surfactant used in the detergent composition of the present invention, sodium laurate and
Fatty acid soaps such as triethanolamine laurate,
Alkylbenzene sulfonate, α-olefin sulfonate, sodium lauryl sulfate, triethanolamine lauryl sulfate, lauryl sulfate, polyoxyethylene (3) ether sulfate such as sodium lauryl ether sulfate, polyoxyethylene (3) coconut oil Amide ether sulfates such as fatty acid sodium amide sulfate, triethanolamine monododecyl phosphate, phosphoric acid esters such as sodium polyoxyethylene dodecyl ether phosphate, cocoyl methyl taurine sodium, acyl methyl taurine salt such as lauroyl methyl taurine sodium, Acyl isethionates such as sodium lauroyl isethionate, disodium lauryl sulfosuccinate, POE (1-4) disodium lauryl sulfosuccinate, polyoxye Ren (5) sulfosuccinic acid type surfactants such as lauric acid monoethanolamide sulfosuccinate disodium, alkyl ether carboxylates,
Cocoyl sarcosine sodium, lauroyl sarcosine sodium, myristoyl sarcosine sodium, lauroyl sarcosine potassium, N-acyl sarcosine salts such as lauroyl sarcosine triethanolamine, cocoyl-N-methyl-β-alanine sodium, lauroyl-N-methyl-β-alanine sodium , Myristoyl-N-methyl-β-alanine sodium, palmitoyl-N-methyl-β-alanine sodium, stearoyl-N-methyl-β-alanine sodium, lauroyl-N-methyl-β-alanine potassium, lauroyl-N
N such as -methyl-β-alanine triethanolamine
-Acyl-β-alanine salts, sodium N-lauroyl aspartate, triethanolamine N-lauroyl aspartate, sodium N-myristoyl aspartate, and other N-acyl aspartates, sodium N-lauroyl glutamate, tri-N-lauroyl glutamate. Examples thereof include amidocarboxylic acid type surfactants such as N-acylglutamates such as ethanolamine, sodium N-cocoylglutamate, and triethanolamine N-cocoylglutamate.

Examples of the cationic surfactant used in the detergent composition of the present invention include quaternary ammonium salt type cationic surfactants such as lauryl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride and distearyl dimethyl ammonium chloride. To be

Examples of the amphoteric surfactant used in the detergent composition of the present invention include alkyl betaine type amphoteric surfactants such as lauryl betaine, amido betaine type amphoteric surfactants such as lauroyl amidopropyl betaine, and 2-alkyl- Imidazoline-type amphoteric surfactants such as N-carboxymethylimidazolinium betaine and 2-alkyl-N-carboxyethylimidazolinium betaine, N-2-hydroxyethyl-N-2-lauric acid amidoethylglycine, N- 2-hydroxyethyl-N-
2-coconut oil fatty acid amide ethylglycine, N-2-hydroxyethyl-N-2-lauric acid amide ethyl-β-
Alanine, N-2-hydroxyethyl-N-2-coconut oil fatty acid amide ethyl-β-alanine, N-carboxymethyl-N- {2- [N '-(2-hydroxyethyl) lauric acid amide] ethyl} glycine, N-carboxymethyl-N- {2- [N '-(2-hydroxyethyl) coconut fatty acid amide] ethyl} glycine, N- {2- [N
Amidoamine type amphoteric surfactants such as-(2-hydroxyethyl) lauric acid amide] ethyl} glycine and N- {2- [N- (2-hydroxyethyl) coconut oil fatty acid amide] ethyl} glycine, alkylsulfobetaine type Examples thereof include amphoteric surfactants and amide sulfobetaine-type amphoteric surfactants such as coconut oil fatty acid amide dimethylhydroxypropyl sulfobetaine.

Examples of the nonionic surfactant used in the detergent composition of the present invention include fatty acid diethanolamides such as coconut oil fatty acid diethanolamide and lauric acid diethanolamide, coconut oil fatty acid monoethanolamide and lauric acid monoethanolamide. Fatty acid monoethanolamides, coconut oil fatty acid diglycolamides, fatty acid diglycolamides such as lauric acid diglycolamide, fatty acid isopropanolamides such as lauric acid isopropanolamide, polyoxyethylene (2) lauric acid monoethanolamide, polyoxyethylene (5) Polyoxyethylene fatty acid monoethanolamide such as coconut oil fatty acid monoethanolamide, fatty acid ester, alkylamine oxide such as lauryldimethylamine oxide, OE higher alcohol ether,
Examples include nonionic surfactants such as POE alkyl phenyl ethers and alkyl glucosides such as decyl glucoside.

The amount of the polyoxypropylene fatty acid isopropanolamide mixture of the present invention to be added to the detergent composition is not particularly limited, but is preferably 0.1 to 100% by weight, more preferably 1 to 30% by weight, based on the detergent. %.
If it is less than 0.1% by weight, the effect is small.

The cleaning composition of the present invention may contain the following additional components, if desired. As additional ingredients,
For example, cationized polymer and cationized guar gum can be mentioned.

Further, the following additional components can also be used if necessary. That is, as additional components, polyhydric alcohols such as glycerin, propylene glycol, 1,3-butylene glycol and sorbitol, silicones such as methylpolysiloxane and oxyalkylene-modified organopolysiloxane, dandruff such as zinc pyrithione and piroctone olamine. Water-soluble polymer substances such as preservatives, hyaluronic acid, collagen, elastin chondroitin sulfate, dermatanic acid, fibronectin, ceramides, chitin, chitosan, cell activating agents such as aloe extract, placenta extract, allantoin, glycyrrhizinate, etc. Anti-inflammatory agent, edetate, pyrophosphate, hexametaphosphate, citric acid, malic acid, chelating agent such as gluconic acid, benzoate, salicylate, sorbate, dehydroacetate, paraoxybenzoate, 2 4,4'-trichloro-2'-hydroxy-diphenyl ether, 3,
Preservatives such as 4,4'-trichlorocarbanito, benzalkonium chloride, hinokitiol, resorcin, fungicides, antioxidants such as dibutylhydroxytoluene, butylhydroxyanisole, propyl gallate, ascorbic acid, fragrances and pigments Can be mentioned.

The state of the detergent composition of the present invention is not limited and may be any state such as liquid, paste, gel, powder and solid. The appearance is generally transparent, pearly, or emulsified, but is not limited to this. In order to produce the detergent composition of the present invention, a compounding method generally used by those skilled in the art may be used.

The cleaning agent of the present invention may be used for any purpose. Typical examples are kitchen detergents, hard surface cleaners,
Detergents such as facial cleansers, cleansing foams, shampoos, body shampoos, and solid detergents.

As described above, the polyoxypropylene fatty acid isopropanolamide mixture of the present invention further improves the performance of fatty acid diethanolamide, which is a typical thickener, and eliminates the drawbacks thereof. In particular, since its physical properties such as melting point and solubility are similar to those of conventional fatty acid diethanolamides that have been conventionally used in the formulation of cosmetics and detergent compositions, etc. With propylene fatty acid isopropanolamide mixture, thickening, foaming, detergency,
Effects such as foaming stability and enhancement of emulsion stability can also be expected. Furthermore, since the polyoxypropylene fatty acid isopropanolamide mixture of the present invention has strong resistance to hydrolysis, it can be used also in a compound having a high pH, which has heretofore been unusable with fatty acid diethanolamide. The use range of the fatty acid diethanolamide is less restricted than that of the conventional fatty acid diethanolamide.

In the conventional fatty acid diethanolamide, when an optimum one for the compounding system is selected,
Only allowed to change the composition of fatty acids,
In the polyoxypropylene fatty acid isopropanolamide mixture of the product of the present invention, not only the fatty acid composition but also the number of moles of propylene oxide added can be appropriately changed. Therefore, there are many performance expression variables to satisfy a wide variety of demands, such as when importance is attached to thickening, when high foaming stability is required, or when sufficient emulsion stability is required. The possibility of addition to the compound is high.

[0059]

The present invention will be described in detail with reference to the following examples, but the present invention is not limited to these examples.

Example 1 (Polyoxypropylene (1)
Preparation of uric acid isopropanolamide) Isopropanolamine 7 was added to 214 g of methyl laurate.
6 g and 1 g of sodium methoxide were added, and by-product methanol was distilled off under reduced pressure while heating and stirring (20 mm
Hg, 100 ° C., 6 hours) to obtain 258 g of lauric acid isopropanolamide. 258 g of this lauric acid isopropanolamide and 58 g of propylene oxide
(1 mol) was charged into an autoclave and stirred at 120 ° C. for 3 hours to synthesize a polyoxypropylene (1) lauric acid isopropanolamide mixture. Yield: 31
6g.

The physical properties were as follows. Melting point: 18 ° C. Hydroxyl value: 179 Amine value: 6.0 IR analysis (Hitachi 270-30, KBr tablets): 331
6,2924,2852,1738,1648,155
4,1464,1378,1264,1124,109
^{4cm -1 1 H-NMR (Bruker} AC-250, CDCl
₃ , TMS internal standard): δ 0.86 ppm (t, 3H,-
_{C 10 H 20 - CH 3)} , 1.13~1.21ppm (m, 6
_{H, (- CH (CH 3} ) -O-) 2), 1.26ppm
_{(Br, 16H, -CH 2 -} ), 1.62ppm (m, 2
_{H, - CH 2 CH 2 CONH} -), 2.14~2.38
ppm (t, 2H, - CH 2 CONH -), 2.68ppm
(Br, 1H, -OH), 3.1 to 3.6 ppm (m, 5
_{H, - CH 2 CH O CH} 2 CHO -), 3.94ppm
(M, 1H, -CH- OH), 5.90ppm (br, 1
H, NH)

Examples 2-8 and Comparative Examples 1-2 (polio
Xypropylene lauric acid isopropanolamide mixture
Preparation of product) Isopropanolamine 7 in 214 g of methyl laurate
6 g and 2 g of sodium methoxide were added, and by-product methanol was distilled off under reduced pressure while heating and stirring (20 mm
Hg, 140 ° C., 3 hours) to obtain 258 g of lauric acid isopropanolamide. 258 g of this lauric acid isopropanolamide was put in an autoclave and the temperature was 90 ° C.
A mixture of polyoxypropylene lauric acid isopropanolamide having various addition mole numbers was introduced by pressurizing the propylene oxide in the amount shown in Table 1 from a propylene oxide introducer into the mixture while heating and stirring the mixture at 120 ° C. for 3 hours. Was synthesized. Table 1 shows various physical property values.

[Table 1]

Example 9 (polyoxypropylene (2) la
Preparation of uric acid isopropanolamide mixture) 257 g of purified lauric acid isopropanolamide and 2.4 g of BF3.ether complex were put into an autoclave, and 116 g of propylene oxide was further added to the autoclave to prepare 1
Reaction was carried out at 50 ° C. for 1 hour. After completion of the reaction, water was added to quench the reaction, and topping was performed under reduced pressure to obtain 373 g of a polyoxypropylene (2) lauric acid isopropanolamide mixture.

Comparative Example 3 (Polyoxyethylene (2) Lau
Preparation of phosphoric acid isopropanolamide) Lauroic acid isopropanolamide (257 g ) was placed in an autoclave and heated to 120 ° C., and then ethylene oxide (88 g, 2 times mole) was blown in a gas state. The mixture was heated and stirred at 120 ° C. for 3 hours and then cooled. The products were unreacted lauric acid isopropanolamide and polyethylene glycol, and the target polyoxyethylene lauric acid isopropanolamide was not obtained.

Example 10 (Polyoxypropylene (1)
Preparation of Lauric Acid Isopropanolamide Mixture) 90 g of isopropanolamine was added to 200 g of lauric acid , and the mixture was heated and stirred at 180 ° C. for 8 hours under a nitrogen stream. The produced water was reacted while distilling off. As a result of HPLC analysis, the content of lauric acid isopropanolamide is 80%.
Met. Besides, it contained N, O-dilauroylisopropanolamine and O-lauroylisopropanolamine, and had a light brown color. After removing unreacted isopropanolamine under reduced pressure, 58 g of propylene oxide was added thereto, and the mixture was autoclaved at 120 ° C. for 1 hour.
A time addition reaction was performed. As a result of HPLC analysis, the content of the target polyoxypropylene fatty acid isopropanolamide mixture was 60%. The obtained product had a blackish brown color and had an unpleasant odor.

Example 11 (Polyoxypropylene (1)
Preparation of lauric acid isopropanolamide mixture) Isopropanolamine 75 g was added to chloroform 1000
g, and 111 g of triethylamine was added,
Cooled to 10 ° C. 219 g of lauric acid chloride was added dropwise while keeping the reaction temperature at 20 ° C. After the dropping was completed, the mixture was stirred at 30 ° C. for 1 hour. After completion of the reaction, the precipitated triethylamine hydrochloride was removed by filtration. The filtrate is 1N
After washing 3 times with 500 ml of hydrochloric acid, 500 ml of saturated sodium bicarbonate water
It was washed 3 times with, and finally with saturated sodium sulfate solution. After drying over anhydrous sodium sulfate, the solvent was removed under reduced pressure to give 244 g of lauric acid isopropanolamide as a white solid.
(95% yield). 244 g of the obtained lauric acid isopropanolamide and 55 g of propylene oxide,
0.5 g of sodium methoxide was placed in an autoclave and heated and stirred at 130 ° C. for 2 hours to add propylene oxide. The resulting polyoxypropylene (1) lauric acid isopropanolamide mixture was 30
It was 0 g (yield 95%). Various analytical values were the same as those obtained by the method of Example 1 except that the hydroxyl value was 177 and the amine value was 11.0.

As described above, the production method using a fatty acid halide such as lauric acid chloride as a starting material requires a reaction solvent such as chloroform or water, and an alkali or a base for trapping the hydrochloric acid produced by the reaction. And
Further, a step of removing salts generated by trapping hydrochloric acid, such as triethylamine hydrochloride and sodium chloride, specifically, steps such as filtration and washing with water are required. Therefore, the yield is slightly lowered. Further, in the step of removing the salt, the base catalyst necessary for the next addition of propylene oxide is also removed from the system, and therefore the base catalyst must be added again at the stage of adding propylene oxide. In addition, the corrosion of the equipment due to hydrochloric acid or salt generated in the acylation reaction is also a problem. As described above, since the method for producing from a fatty acid halide is complicated in operation, requires an auxiliary material, and has a problem of corrosion, the industrial production method is the production of the present invention described in Example 1. It turns out that it is not suitable compared to the law.

Comparative Example 4 (Polyoxypropylene (1)
Preparation of uric acid isopropanolamide) Isopropanolamine 7 was added to 214 g of methyl laurate.
5 g and 2 g of sodium methoxide were added, and the resulting methanol was distilled off under reduced pressure while heating and stirring (20 mmH
g, 140 ° C., 1 hour) to obtain 258 g of lauric acid isopropanolamide. The amine value of this product is 6.2.
Met. This was dissolved in 3000 ml of xylene and washed twice with 800 ml of 2% by weight hydrochloric acid water. Then, after washing 3 times with 800 ml of saturated saline, it was dried over anhydrous sodium sulfate. After removing the solvent under reduced pressure, the residue was recrystallized from THF-toluene to obtain 206 g of purified lauric acid isopropanolamide (yield 80%). The amine value of this product was 0.01. This was placed in an autoclave, and 46 g (1 mol) of propylene oxide was added,
Although the mixture was stirred at 150 ° C. for 6 hours, it did not react and only recovered the raw material.

Melting point measurement The melting point was measured according to the Japanese Pharmacopoeia B-414 melting point measuring method (first method). For compounds that are liquid at room temperature or that are difficult to fill in capillaries, refer to Japanese Pharmacopoeia B-
The melting point was defined as the freezing point measured according to the 116 Freezing Point Measurement Method. Table 2 shows the melting points of the polyoxypropylene fatty acid isopropanolamide of the present invention and, for reference, the melting points of the fatty acid isopropanolamide and the fatty acid diethanolamide, which are propylene oxide addition raw materials.

[0070]

[Table 2]

As shown in Table 2, the reaction product to which propylene oxide was added had a melting point considerably lower than that of the fatty acid isopropanolamide before addition.
Among the polyoxypropylene fatty acid isopropanolamides of the product of the present invention, those having a large number of moles of propylene oxide added were liquid at room temperature. That is, this melting point value was lower than the melting point of the corresponding fatty acid diethanolamide. Generally, when preparing a blended product, a liquid compound is easier to handle than a solid or powdery compound. However, even if it is a solid or a powder, if it is easily dissolved by heating, it may be melted once and then added to the compounded product. At that time, if the melting point exceeds 60 ° C, it is dissolved in a heated water bath. Even if you try to do so, it does not melt easily and is inconvenient to handle. In this respect, the polyoxypropylene fatty acid isopropanolamide mixture of the present invention has a low melting point, and therefore it can be made into a liquid state by slightly heating it, and as a result, the handling property at the time of compounding was extremely improved.

27 g of isopropanol and 71 g of purified water were added to and dissolved in 2 g of the sample for hydrolysis test , citric acid or caustic soda was added to adjust the pH to a predetermined value, and this solution was stored at 50 ° C. for 1 month. During that time, measure the pH every week, and if it seems to change, use citric acid or caustic soda to restore the original pH.
Adjusted to pH. One month later, the lauric acid content in the sample solution produced by hydrolysis was measured by GLC (absolute calibration curve method). The hydrolysis rate was calculated from the lauric acid content by the following formula. Hydrolysis rate (%) = (lauric acid content) / (mol number of charged sample × 200.3) × 100 Test results are shown in Table 3.

[0073]

[Table 3]

As shown in Table 3, lauric acid diethanolamide was found to be susceptible to hydrolysis. In particular, it was confirmed that decomposition was easily performed at pH 3 or lower or 9 or higher. On the other hand, the polyoxypropylene fatty acid isopropanolamide mixture of the present invention showed a low hydrolysis rate in a wide pH range like lauric acid isopropanolamide. Therefore, it can be said that the polyoxypropylene fatty acid isopropanolamide mixture of the present invention is stable in a wide range of pH, and there are few restrictions on the pH when it is attempted to mix it.

Ocular Mucosal Irritation Test To a Japanese white rabbit female (14 weeks old), 0.1 ml of a 10% sample solution or suspension was dropped into the lower right eyelid sac, and the upper and lower eyelids were put together for about 5 seconds and well contacted. , Left as it is. The other side (left eye) served as an untreated control. Judgment is administration 1,
Drai after 3,6 hours and after 1,2,3,4,7 days
It was performed according to the criteria of the ze method. Based on the maximum value of the average stimulation value and the duration of the score, the safety evaluation criteria are KAY
It was performed based on the eye irritation evaluation criteria of & CALANDRA. The evaluation has the following eight levels. 1: No irritation 2: Practically no irritation 3: Minimal irritation 4: Mild irritation 5: Moderate irritation 6: Intense irritation 7: Extremely irritation 8: Maximum irritation The test results are shown in Table 4.

[0076]

[Table 4]

As shown in Table 4, it was confirmed that the polyoxypropylene fatty acid isopropanolamide mixture of the present invention had substantially no ocular mucosal irritation. In contrast, a slight irritation was observed with the compounds having a propylene oxide addition mole number outside the present invention. In addition, a slight irritation was observed with the fatty acid isopropanolamide. From the above results, it was confirmed that the polyoxypropylene fatty acid isopropanolamide of the present invention is a compound that can be safely used in detergents such as shampoo and cosmetics such as rinses.

[0078] In each of Examples 12-15 and Comparative Examples 5-11 Examples 12-15 and Comparative Examples 5-11, using a polyoxypropylene fatty acid isopropanol amide and commercially available fatty acid alkanolamides, the formulations shown in Table 5 A composition of composition was prepared. The obtained composition was subjected to a thickening test, a foaming force test and a foaming stability test. Each test was performed by the following method.

1) Thickening test 7.5 ml of a sample was put in a small amount of a sample adapter and placed at 25 ° C.
After the temperature was kept at, the viscosity was measured with a B-type viscometer (B8M manufactured by Tokyo Keiki Co., Ltd.). 2) Foaming power test The detergent was diluted with distilled water so that the pure content of the active agent was 0.25%, and the foaming power was measured according to the method described in JIS K3362. The evaluation criteria were set as follows. ∘: Very good foaming, foaming power of 200 mm or more ○: Good foaming, foaming power of 180 mm or more, less than 200 mm △ ... Normal foaming, foaming power of 150 mm or more, less than 180 mm × ... Poor foaming, foaming power of 150 mm Less than

3) Foaming Stability Test When conducting the loss-miles foaming force test described above, the foaming force immediately after charging and the foaming force after 5 minutes were measured to obtain the foam damping rate. Attenuation rate (%) = {(FH ₀ −FH ₅ ) / (FH ₀ )} ×
100 However, in the above formula, FH ₀ : Foaming power immediately after charging FH ₅ : Foaming power after 5 minutes Evaluation criteria were set as follows. ∘: Foaming stability is extremely good, damping rate is less than 10% ◯: Foaming stability is good, damping rate is 10 to 20% △: Foaming stability is normal, damping rate is 21 to 50% × ... Foaming stability Table 5 shows the test results of 50% or more of attenuation rate, which is poor in property.

[0081]

[Table 5]

As is clear from the results shown in Table 5, since the viscosity of the fatty acid alkanolamide derivative is higher than that of the polyoxyethylene lauryl ether sulfate Na alone, the viscosity of any fatty acid alkanolamide derivative is increased. It was confirmed to have. However, the polyoxypropylene fatty acid isopropanolamide mixture of the present invention is suitable because it has a particularly suitable viscosity. Moreover, the foaming power is higher when the fatty acid alkanolamide derivative is contained than in the case of only polyoxyethylene lauryl ether sulfate Na, but when the polyoxypropylene fatty acid isopropanolamide of the present invention is contained, The rate of increase in foaming power was greater than that with other fatty acid alkanolamides. A similar tendency was observed for foam stability. From the above results, it was confirmed that the polyoxypropylene fatty acid isopropanolamide of the present invention has excellent properties as a thickener, a foaming agent and a foaming stabilizer.

Examples 16 to 19 and Comparative Examples 12 to 17 Samples in the amounts shown in Table 6 were dissolved in distilled water, and the pH was adjusted to 7 with citric acid or caustic soda to prepare sample solutions. 30 ml of 10 ml of this sample solution and 2 g of olive oil
The mixture was placed in a test tube with a ground stopper, shaken vigorously 50 times, and allowed to stand. After 30 minutes, the state inside the test tube was observed. "Insoluble" when the sample is not dissolved in distilled water, "Emulsified" when the sample is dissolved in distilled water and does not separate into an aqueous layer and an emulsified layer (including oil layer) and is emulsified When was dissolved in distilled water and separated into an aqueous layer and an emulsified layer, the thickness of the emulsified layer was measured in mm, and this was taken as the emulsifying power. Table 6 shows the test results.

[0084]

[Table 6]

As is clear from the results shown in Table 6, the use of the polyoxypropylene fatty acid isopropanolamide mixture of the present invention reduced the volume of the aqueous layer. This means that the volume of the emulsion layer is larger, which means that the emulsifying power of the compound is excellent. Therefore, it was confirmed that the product of the present invention has excellent emulsifying power and is useful as an emulsifier.

Examples 20 to 23 and Comparative Examples 18 to 23 The polyoxypropylene fatty acid isopropanolamide mixtures and the commercially available fatty acid alkanolamides shown in Table 7 below were measured for the dispersibility in oil. The dispersion test was performed by the following method. Average particle size 1 as inorganic powder
A mixture of 100 g of μ alumina powder and 100 g of titanium oxide powder having an average particle size of 0.8 μ was used, and 500 g of light oil prepared by dissolving the amount of the dispersant shown in Table 14 with respect to the weight of this inorganic powder was used as the inorganic powder. Were mixed and the dispersibility was tested. In this test, the test material was placed in a 2 liter beaker and a 120-blade impeller was used.
After stirring for 1 minute at rpm, let it stand for 1 minute, observe the remaining state of alumina powder and titanium oxide powder at the bottom of the beaker, and either all are dispersed in oil, or most of the powder is dispersed in oil. However, for the one remaining slightly at the bottom, use a homogenizer at 5 rpm at 4000 rpm.
After vigorously stirring for 1 minute, leave it still in a 500 ml measuring cylinder for 1 day, then drop a glass rod having a diameter of 5 mm and a weight of 50 g into the dispersion through a guide provided on the top of the cylinder, and observe the precipitation state to check the dispersion stability. It was evaluated in two stages. ○: The rod reached the bottom of the cylinder. B: The rod stopped without reaching the bottom of the cylinder, and a consolidation layer was generated. X: Dispersion did not occur at the initial stirring. Table 7 shows the test results.

[0087]

[Table 7]

As is clear from Table 7, the polyoxypropylene fatty acid isopropanolamide of the present invention has an excellent dispersibility in oil and is useful as a dispersant in oil.

Examples 24-26 and Comparative Examples 24-29 Using the polyoxypropylene fatty acid isopropanolamide mixture of the present invention and commercially available fatty acid alkanolamides, the lime soap dispersancy was measured. The test was conducted by the following method. The test is based on the method of Borghetty et al. (J. Am.O.
il Chem. Soc. 27, 88 (1950)). A 0.5 wt% aqueous solution of sodium oleate was placed in a 50 ml stoppered test tube and then 0.25 wt% of the sample to be tested
5ml aqueous solution of CaCl ₂ · 2H ₂ O 0.8824g
Then, 10 ml of hard water prepared by dissolving 0.8132 g of MgCl ₂ .6H ₂ O in 1 liter of distilled water was added, and distilled water was added so that the total amount became 30 ml. After repeating upside down 20 times, leave the test tube in a constant temperature bath at 25 ° C for 30 seconds, observe the condition of lime soap particles, and add a 0.25 wt% sample aqueous solution until precipitation no longer occurs. It was Assuming that the amount of the sample aqueous solution at that time was Aml, the lime soap dispersive power (LSDP) was calculated from the following formula. LSDP (%) = (Aml × 0.0025) /0.025
The results of × 100 test are shown in Table 8.

[0090]

[Table 8]

As is clear from Table 8, the polyoxypropylene fatty acid isopropanolamide mixture of the present invention was confirmed to have excellent lime soap dispersibility.
Therefore, the product of the present invention is useful as a dispersant in water. The results also show that the detergent containing the product of the present invention has excellent hard water resistance.

Examples 27 to 30 and Comparative Examples 30 to 35 Solubilizing power was measured using the polyoxypropylene fatty acid isopropanolamide of the present invention and commercially available fatty acid alkanolamides. The test was conducted by the following method. A sample solution having the composition shown in Table 9 was prepared. 20 ml of this sample solution was placed in a test tube with a stopper of 30 ml, and the temperature was adjusted to 20 ° C. in a constant temperature bath. Toluene was added dropwise to the sample solution with a microsyringe while vigorously shaking the test tube, and the solubilization limit amount of the test solution was indicated by the amount of toluene (μl) added until just before cloudiness occurred. Table 9 shows the test results.

[0093]

[Table 9]

As is clear from the results in Table 9, the polyoxypropylene fatty acid isopropanolamide of the present invention had a high solubilization amount. This means that the product of the present invention has a higher solubilizing power than other fatty acid alkanolamides, polyoxypropylene fatty acid isopropanolamides or polyoxypropylene fatty acid isopropanolamides outside the scope of the present invention. Therefore, the product of the present invention is useful as a solubilizing agent.

Examples 31 to 34 and Comparative Examples 36 to 41 In Examples 31 to 34 and Comparative Examples 36 to 41, hand creams having the compositions shown in Table 10 were prepared.
The obtained cosmetics were subjected to the following emulsion stability test and sensory test. The test methods were as follows. 1) Emulsion stability test After heating component A and component B separately to 75 ° C., component B
Ingredient A was added to. At this time, it was emulsified by vigorous stirring using a 4-blade impeller. After cooling to room temperature while continuing stirring, the emulsion was stored at room temperature for 1 month and examined for emulsification. The evaluation criteria were set as follows. ◎ ... Completely emulsified ○ ... Extremely separated part is observed △ ... Partially separated × ... Completely separated 2) Sensory test Actually conducted by 10 specialized panelists A sensory test was performed on the feel after use. The evaluation criteria were set as follows. ⊚: Answered by 8 or more people ○: Answered by 6-7 people △: Answered by 4-5 people ×: Answered by 3 people or less Table 10 shows the test results.

[0096]

[Table 10]

As is clear from Table 10, the product containing the polyoxypropylene fatty acid isopropanolamide of the present invention was excellent in emulsion stability. Also, the usability was excellent. In comparison, fatty acid alkanolamides and the like and those containing polyoxypropylene fatty acid isopropanolamide outside the scope of the present invention were inferior in emulsion stability and usability.

Examples 35-38 and Comparative Examples 42-47 In Examples 35-38 and Comparative Examples 42-47, cleaning agents having the compositions shown in Table 11 were prepared. The obtained product is subjected to the following foaming power test, detergency test, foaming stability test,
It was subjected to a thickening test, a cold resistance test and a protein denaturation test. The test method for this was as follows. 1) Foaming power test Same as the method described in Example 12. 2) Detergency test 0.1% SudanIII was added to beef tallow as an indicator,
Apply this 5% to a porcelain dish (25 cm in diameter)
The washing power was defined as the washing power, which was obtained by scrubbing with a sponge soaked in 30 g of a 10% by weight washing solution and washing the dishes until the beef tallow could no longer be washed from the dishes. 3) Foaming stability test Same as the method described in Example 12.

4) Thickening Test The viscosity was measured by the same method as described in Example 12 to check whether or not there was thickening. The evaluation criteria were set as follows. ⊚: Significant thickening effect ○: Thickening effect ×: No thickening effect observed 5) Cold resistance test Put the sample in a test tube and store it in a freezer at -5 ° C for 7 days to see turbidity. I checked the cold resistance. The evaluation criteria were set as follows. ◎ ... No turbidity after storage at -5 ° C for 7 days ◯ ... Transparency at room temperature, but slight turbidity at -5 ° C, storage for 7 days △ ... Cloudy at room temperature × ... Crystal precipitation

6) Protein denaturation rate test Using aqueous gel filtration high performance liquid chromatography, the ovalbumin denaturation rate when the sample was added to the ovalbumin pH7 buffer solution so that the sample concentration was 1% was 220 nm.
It measured using the absorption peak of. Denaturation rate (%) = (H ₀ −H _S ) / H ₀ × 100 H ₀ : Height of 220 nm absorption peak of ovalbumin H _S : 22 when sample is added to ovalbumin buffer solution
The height evaluation standard of the 0 nm absorption peak was set as follows. ⊚: Ovalbumin denaturation rate of less than 10% ◯: Ovalbumin denaturation rate of 10 to 29% Δ: Ovalbumin denaturation rate of 30 to 59% x: Ovalbumin denaturation rate of 60% or more The test results are shown in Table 11.

[0101]

[Table 11]

As is clear from the results shown in Table 11, the cleaning agents of Examples 35 to 38 containing the polyoxypropylene fatty acid isopropanolamide of the present invention are excellent in foaming power, cleaning power and foaming stability, and are suitable. It had a thickening property, excellent cold resistance, and low irritation. On the other hand, the cleaning agents of Comparative Examples 42 to 47 containing the polyoxypropylene fatty acid isopropanolamide and the fatty acid alkanolamide and the polyoxyethylene fatty acid monoethanolamide outside the range used in the present invention have foaming power, cleaning power, and It was inferior in any of foam stability, thickening, cold resistance and irritation.

Examples 39 to 48 and Comparative Examples 48 to 55 In Examples 39 to 48 and Comparative Examples 48 to 55, cleaning agents having the compositions shown in Table 12 were prepared. The obtained product was subjected to a foaming power test, a detergency test, a foaming stability test, a thickening test, a cold resistance test and a protein denaturation test. Table 12 shows the test results.

[0104]

[Table 12]

As is clear from the results in Table 12, at least one selected from the polyoxypropylene fatty acid isopropanolamide mixture of the present invention and an anionic surfactant, amphoteric surfactant, cationic surfactant and nonionic surfactant. The cleaning agents of Examples 39 to 48 consisting of one surfactant have excellent foaming power, cleaning power and foaming stability, have an appropriate thickening property, are excellent in cold resistance, and are also irritating. It was low. On the other hand, selected from polyoxypropylene fatty acid isopropanolamide, fatty acid alkanolamide and polyoxyethylene fatty acid monoethanolamide and anionic surfactants, amphoteric surfactants, cationic surfactants and nonionic surfactants outside the scope of the present invention. Comparative Examples 48-5 comprising at least one surfactant
The cleaning agent of No. 5 has foaming power, cleaning power, foaming stability, thickening,
It was inferior in either cold resistance or irritation.

Examples 49 to 63 and Comparative Examples 56 to 70 In Examples 49 to 63 and Comparative Examples 56 to 70, cleaning agents having the compositions shown in Tables 13 and 14 were prepared. The obtained product was subjected to a foaming power test, a detergency test, a foaming stability test, a thickening test, a cold resistance test and a protein denaturation test. The test results are shown in Tables 13 and 14.

[0107]

[Table 13]

[0108]

[Table 14]

As is clear from the results shown in Tables 13 and 14, the detergent using the polyoxypropylene fatty acid isopropanolamide of the present invention has lower cold resistance and protein denaturation rate than the detergent containing fatty acid diethanolamide. Despite the same level of foaming power, cleaning power,
It was excellent in foaming stability and thickening. Therefore, it was confirmed that, in the conventional formulation using the fatty acid diethanolamide, the use of the polyoxypropylene fatty acid isopropanolamide of the present invention in place of the fatty acid diethanolamide provides a more excellent detergent.
In addition, the cleaning composition of Example 63 has a higher pH than the cleaning composition of Comparative Example 70 even after being stored at 50 ° C. for one month.
There was almost no decline. Generally, in the case of blending based on fatty acid soap, the pH is adjusted to around 10, so that it is difficult to use fatty acid diethanolamide which is easily hydrolyzed at such a high pH. However, since the polyoxypropylene fatty acid isopropanolamide of the present invention is stable even at the above high pH, it was confirmed that it can be blended with fatty acid soap.

Example 64 A cream having the following composition was prepared by a usual method and subjected to the same tests as in Example 31. As a result, the emulsion stability and the feeling of use were excellent. Component weight% Polyethylene glycol monostearate (40EO) 1.0 Polyoxypropylene (2) isopropanol stearate amide mixture 1.0 Self-emulsifying glyceryl monostearate 5.0 stearic acid 5.0 Behenyl alcohol 1.0-Liquid paraffin 10.0-Cetyl octanoate 10.0-Ethyl paraoxybenzoate 0.2-Glycerin 5.0-Luffa extract 1.0-Preservative 0.5-Purified water balance

Example 65 A milky lotion having the following composition was prepared by a usual method, and its performance was evaluated. As a result, a moist feel was exhibited. % By weight Component of Example 1 1.0 Polyoxyethylene sorbitan monostearate (20 EO) 1.0 Polyoxyethylene sorbit tetraoleate (60 EO) 0.5 Stearic acid 0.5 Behenyl alcohol 0.5 ・ Avocado oil 3.0 ・ Glyceryl trioctanoate 5.0 ・ 1,3-butylene glycol 5.0 ・ Xanthan gum 0.1 ・ Disodium edetate 0.2 ・ Preservative 0.1 ・ Purified water balance

Example 66 A milky lotion having the following composition was prepared by a usual method, and its performance was evaluated. As a result, a moist feel was exhibited. Component weight% Polyoxyethylene hydrogenated castor oil (60EO) 8.0-Ethanol 15.0-Polyoxypropylene (1) myristic acid isopropanol amide mixture 0.5-Behenyl alcohol 1.0-Methyl paraoxybenzoate 0.1・ Glycerin 5.0 ・ Purified water balance

Example 67 A stick-form antiperspirant having the following composition was prepared by a usual method and its performance was evaluated. As a result, a good antiperspirant action was shown. % By weight Component mixture of Example 3 28.5 POP (3) myristyl ether 15.0 Propylene glycol 30.0 Aluminum chlorohydrate propylene glycol complex 20.0 Perfume 1.0 Purified water balance

Example 68 An aftershaving lotion having the following composition was prepared by a usual method and its performance was evaluated. As a result, the tingling sensation after shaving was reduced. Component wt% Propylene glycol 51.8 Purified water balance Polyoxypropylene (1) coconut oil fatty acid isopropanol amide mixture 7.5 POE (75) lanolin 1.2 sodium stearate 8.5 Pigment 0.1. 1 ・ Perfume oil 3.0 ・ Alcohol 5.0 ・ POE (20) sorbitan monolaurate 3.0

Example 69 A bath agent having the following composition was prepared by a usual method and its performance was evaluated. As a result, a moist feeling on the skin after bathing was shown. Component weight%・ Sodium sulfate 54.0 ・ Sodium hydrocarbon 10.0 ・ Sodium carbonate 5.0 ・ Sodium chloride 30.0 ・ Polyoxypropylene (1) linoleic acid isopropanol amide mixture 1.0

Example 70 A poultice of the following composition was prepared by a usual method and its performance was evaluated. Component % by weight • Polyacrylic acid 30.0 • Crotamiton 1.0 • Sodium polyacrylate 7.0 • Aluminum chloride 0.3 • Glycerin 20.0 • Sorbitan monooleate 1.0 • Polyoxypropylene (20) Oleic acid isopropanol amide mixture 0.7 ・ Titanium oxide 5.0 ・ Purified water balance

Example 71 A creamy foundation having the following composition was prepared by a usual method, and its performance was evaluated. As a result, it had good elongation during use and an excellent feeling in use. Component % by weight Dimethylpolysiloxane (6cs) 10.0-Methylphenylpolysiloxane 3.0-Octamethylcyclotetrasiloxane 10.0-Polyoxyalkylene-modified silicone 5.0-Compound mixture of Example 8 0.5・ Titanium oxide 5.0 ・ Serisite 2.0 ・ Talc 3.0 ・ Red iron oxide 0.4 ・ Iron oxide yellow 0.7 ・ Iron oxide black 0.1 ・ Glycerin 5.0 ・ Phosphoramidon 0.25 ・ 6-amino -N-caproic acid 0.5-preservative proper amount-perfume proper amount-purified water balance

Example 72 A pack agent having the following composition was prepared by a usual method, and its performance was evaluated. As a result, spreadability during application was good and peelability was excellent. Component weight% -Dipropylene glycol 3.0-Polyethylene glycol 3.0-1, 3-butylene glycol 1.0-Glycerin 2.0-Sodium pyrrolidonecarboxylate 1.0-Lactic acid 0.5-Sodium lactate 0. 5 ・ Polyvinyl alcohol 12.0 ・ Polyoxypropylene (10) isostearic acid isopropanolamide mixture 0.3 ・ Ethanol 3.0 ・ Polyoxyethylene polyoxypropylene decyl tetradecyl ether 0.3 ・ Preservative proper amount ・ Perfume proper amount ・ Purification Remaining water

As is clear from the results of Examples 64 to 72, the skin cosmetics containing the polyoxypropylene fatty acid isopropanolamide mixture of the present invention were excellent in emulsion stability and feeling during or after use.

Example 73 A hair conditioner having the following composition was prepared by a usual method and its performance was evaluated. As a result, the hair after use showed a moist feel. % By weight of component, compound mixture of Example 4 1.0, polyvinylpyrrolidone 2.0, hydrolyzed collagen peptide 0.2, ethanol 5.0, purified water balance

Example 74 A hair brushing agent having the following composition was prepared by a usual method and its performance was evaluated. As a result, it was found that the combability was excellent. Component weight% -Cocoyl arginine ethyl ester-PCA salt 0.5-Ethanol 5.0-Polyoxypropylene (5) palmitic acid isopropanol amide mixture 0.1-Methylparaben 0.1-Perfume 0.1-Purified water balance

Example 75 A hair cream having the following composition was prepared by a usual method,
When subjected to the same tests as in Example 31, the emulsion stability and the feeling of use were excellent. Ingredient wt% Liquid paraffin 10.0 Squalane 7.0 Jojoba oil 3.0 Solid paraffin 3.0 Polyoxyethylene cetyl ether 1.5 Polyoxypropylene (1) isopropanol amide capric acid mixture 0. 5 ・ Sorbitan sesquioleate 0.8 ・ Preservative 0.3 ・ Purified water balance

Example 76 A hair treatment cream having the following composition was prepared by a usual method and subjected to the same tests as in Example 31. As a result, the emulsion stability was good and the hair had a moisturizing feel after use. Gave. Component weight%・ Avocado oil 5.0 ・ Squalane 7.0 ・ Liquid paraffin 10.0 ・ Stearic acid 3.0 ・ Glycerin monostearate 3.0 ・ Polyoxypropylene (5) palm kernel oil fatty acid isopropanolamide mixture 2 0.0-lanolin alcohol 5.0-sodium edetate 0.1-preservative 0.2-purified water balance

Example 77 A hair rinse having the following composition was prepared by a usual method and its performance was evaluated. As a result, it was found that the hair was smooth to the fingers and moisturized after use. Component wt% -Cetyl alcohol 3.0-Liquid paraffin 3.0-Cetyl octanoate 8.0-Polyoxypropylene (2) Coconut oil fatty acid isopropanol amide mixture 2.0-Stearyltrimethylammonium chloride 3.0-Paraoxybenzoic acid Methyl acid 0.1 ・ Purified water balance

Example 78 A blow dry conditioner having the following composition was prepared, and its performance was evaluated. As a result, the hair after blow had less damage and showed a moist feel. Component weight%. Quaternized polyvinylpyrrolidone 2.0. Oleyldimethylbenzylammonium chloride 0.6. POE (20) sorbitan monolaurate 0.2. Compound mixture of Example 5 0.3. Ethanol 3.0. Purified water balance

Example 79 A first agent for permanent wave having the following composition was prepared and its performance was evaluated. As a result, excellent set persistence was shown. In addition, the hair had little damage after use and exhibited excellent moisturizing feeling and gloss. % By weight of components Cetyltrimethylammonium chloride 4.0 Polyether-modified silicone 1.5 Ammonium thioglycolate 12.0 Silk fibroin peptide 0.5 Monoethanolamine 0.8 Emulsifier 1.0 Example Compound mixture of 7 0.3 ・ Lauric acid diethanolamide 0.3 ・ Dipotassium glycyrrhizinate 0.05 ・ EDTA 0.1 ・ Ammonia water pH = 9 amount ・ Purified water balance

As is clear from the results of Examples 73 to 79, the hair cosmetics containing the polyoxypropylene fatty acid isopropanolamide mixture of the present invention were excellent in emulsion stability. Also, since there is little irritation to the hair,
It gave a good feeling to the hair after use.

Example 80 A rinse-inclusive shampoo having the following composition was prepared, and Example 3 was prepared.
The same test as 5 was performed. Component weight% N-carboxymethyl-N- {2- [2-hydroxyethyl-coconut oil fatty acid amide] ethyl} glycine 20.0-N-cocoyl-L-glutamic acid triethanolamine 5.0-2-coconut Oil alkyl-N-carboxyethyl-N-hydroxy-ethylimidazolinium betaine 10.0-Palm oil fatty acid diethanolamide 1.0-Polyoxypropylene (0.5) coconut oil fatty acid isopropanolamide mixture 1.0-Stearyl chloride Trimethylammonium 1.5 Cetyl octanoate 0.5 Carboxymethyl chitin 0.1 Hyaluronic acid 0.1 Sodium edetate 0.1 Preservative 0.1 Purified water balance Table 15 shows the test results.

Example 81 A conditioning shampoo having the following composition was prepared and subjected to the same test as in Example 35. Component wt% Polyoxyethylene (3) sodium lauryl sulfate 10.0-Lauroyl-N-methyl-β-alanine sodium 20.0-Polyoxyethylene (3) coconut oil fatty acid monoethanolamide sodium sulfate 2.0- Cationized guar gum 0.3-Lauric acid monoethanolamide 2.0-Compound mixture of Example 5 1.0-Glycerin 3.0-Sodium edetate 0.1-Citric acid pH = 6.5 amount-Purification Table 15 shows the water balance test results.

[0130]Example 82 A pearly shampoo having the following composition was prepared and used as Example 35.
It was subjected to the same test. Component weight% -N-2-hydroxyethyl-N-2-coconut oil fatty acid amide ethylglycine 15.0-2-coconut oil alkyl-N-carboxymethyl-N-hydroxyethyl imidazolinium betaine (30%) 10.0-Palm Oil fatty acid amide dimethylpropyl betaine 5.0 Lauroyl-N-methyltaurine sodium 5.0 Polyoxypropylene (0.3) coconut oil fatty acid isopropanolamide mixture 1.0 Palm oil fatty acid diethanolamide 2.0 Palm oil Fatty acid monoethanolamide 1.5 ・ Casodium soda pH = 6 amount ・ Methylparaben 0.1 ・ Perfume proper amount ・ Purified water balance Table 15 shows the test results.

Example 83 A gel shampoo having the following composition was prepared and subjected to the same test as in Example 35. Component weight% Polyoxyethylene (3) lauric acid monoethanolamide sodium sulfate 25.0 Lauric acid isopropanolamide 8.0 Polyoxypropylene (0.5) capric acid isopropanol amide mixture 1.0 Carboxymethyl chitin 0.1-Methylparaben 0.1-EDTA 0.1-Citric acid pH = 7.0 Amount-Purified water Remainder Table 15 shows the test results.

Example 84 A shampoo having the following composition was prepared and subjected to the same test as in Example 35. Component wt% -C14-α olefin sulfonate 5.0-Sodium cocoyl isethionate 5.0-Lauroyl-N-methyltaurine sodium 5.0-Oxyalkylene-modified organopolysiloxane (20% modification: polyoxyethylene 20% by weight of the group) 1.0-Compound mixture of Example 5.0-Lauric acid monoethanolamide 2.0-Methylparaben 0.1-EDTA 0.1-Purified water Residual test results are shown in Table 15.

Example 85 A shampoo having the following composition was prepared and subjected to the same tests as in Example 35. Ingredient wt% Sodium lauryl sulphate 15.0 POE (3) Sodium lauryl ether carboxylate 5.0 Sodium mono (polyoxyethylene (6) lauric acid amide) phosphate 4.0 4.0 Polyoxypropylene (1) Palmitic acid isopropanol amide mixture 3.0. Methylparaben 0.1. EDTA 0.1. Purified water Residual test results are shown in Table 15.

Example 86 A body shampoo having the following composition was prepared and subjected to the same test as in Example 35. Component weight% 2-lauryl-N-carboxymethyl-N-hydroxyethyl imidazolinium betaine (30%) 20.0-triethanolamine monododecylphosphate 5.0-polyoxypropylene (1) isopropanol myristate Amide mixture 3.0-Triethanolamine laurate 7.0-Methylparaben 0.1-EDTA 0.1-Purified water balance Table 15 shows the test results.

Example 87 A body shampoo having the following composition was prepared and subjected to the same test as that of Example 35. Component weight% Polyoxyethylene (3) lauric acid monoethanolamide sodium sulfate (30%) 10.0 Polyoxyethylene (5) lauric acid monoethanolamide disodium sulfosuccinate (30%) 5.0 Lauroyl Sarcosine sodium 5.0-Lauryl dimethylamine oxide 4.0-Compound mixture of Example 1.0-Lauric acid diethanolamide 3.0-Ethanol 2.0-Purified water Residual test results are shown in Table 15.

Example 88 A face wash having the following composition was prepared and subjected to the same tests as in Example 35. Composition weight% N-2-hydroxyethyl-N-2-coconut oil fatty acid amide Ethyl-β-alanine (30%) 60.0 Lauric acid diethanolamide 7.0 ・ 2-Alkyl-N-carboxymethyl- N-hydroxy-ethyl imidazolinium betaine (30%) 5.0-monoammonium glycyrrhizinate 0.2-polyoxypropylene (2) isostearic acid isopropanol amide mixture 1.0-polyoxyethylene (2) laurate monoethanol Amide 0.5-Allantoin 0.5-Methylparaben 0.1-Amount of citric acid pH = 6.5-Purified water The balance The test results are shown in Table 15.

Example 89 A hard surface cleaner having the following composition was prepared and subjected to the same tests as in Example 35. Component weight% Polyoxypropylene (1) stearic acid isopropanol amide mixture 3.0 ・ Sodium xylene sulfonate 6.0 ・ Trisodium phosphate 5.0 ・ POP (2) methyl ether 4.0 ・ Pine oil 2. 0-Purified water The balance test results are shown in Table 15.

Example 90 A kitchen detergent having the following composition was prepared and subjected to the same tests as in Example 35. Ingredient weight% sodium α-olefin sulfonate 15.0 laurylamide dimethyl hydroxypropyl sulfobetaine (30%) 5.0 lauryl glucoside 3.0 POE (2) lauric acid monoethanolamide 2.0 edet Acid salt 0.1-Polyoxypropylene (1.5) oleic acid isopropanol amide mixture 0.3-Purified water balance Table 15 shows the test results.

Example 91 An automatic dishwashing detergent of the following composition was prepared and Example 35
The same test was performed. Component % by weight- Na lauryl benzene sulfonate 20.0-Sodium xylene sulfonate 5.4-Sodium sulfate 1.0-Lauryl alcohol ammonium sulfate 8.35-Polyoxypropylene (0.5) myristic acid isopropanolamide mixture 5. 0-Purified water The balance test results are shown in Table 15.

Example 92 An oven cleaner having the following composition was prepared and subjected to the same tests as in Example 35. This cleaning agent was particularly effective for removing oil stains that were thermally deteriorated. Component weight% POE (9) sodium nonylphenyl ether sulfate 3.0 POE (9) sodium nonylsulfophenyl ether sulfate 3.0 sodium hydroxide 4.0 polyoxypropylene (1) coconut oil fatty acid isopropanol amide Mixture 5.0 • Purified water The balance test results are shown in Table 15.

[0141]

[Table 15]

As is apparent from the results in Table 15, the cleaning agents of Examples 80 to 92 containing the polyoxypropylene fatty acid isopropanolamide mixture of the present invention have a foaming power, a cleaning power, a foaming stability and an improved foaming power. It was confirmed that it has excellent viscosity and cold resistance, and has a low protein denaturation rate.

Example 93 An enzyme-containing detergent having the following composition was prepared and its performance was evaluated. As a result, it showed excellent detergency. Component weight% POE (6) C10 | 14 Fatty alcohol ether 17.0 Alkylbenzene sulfonic acid diethanolamine salt 60.0 Polyoxypropylene (1) coconut oil fatty acid isopropanol amide mixture 22.0 Enzyme AP 0.2 Lipase A 0.15 ・ Hard water (100ppm) 0.65

Example 94 A solid detergent having the following composition was prepared by a usual mechanical kneading method,
When its performance was evaluated, the skin after use showed an excellent refreshing feeling. Component weight%・ Soap substrate (beef tallow: coconut = 8: 2) 93.3 ・ N-lauroyl-L-sodium aspartate 2.0 ・ Titanium oxide 0.1 ・ Edetate 0.1 ・ Example 4 Compound mixture of 4.5

Example 95 A solid detergent having the following composition was prepared by a usual mechanical kneading method,
When its performance was evaluated, the skin after use showed an excellent moist feeling. Component wt% N-lauroyl-L-glutamate monosodium 50.0-N-oleoyl-L-glutamate monosodium 41.0-Myristyl alcohol 8.0-Compound mixture of Example 7 1.0

Example 96 A bubble bath agent having the following composition was prepared and its performance was evaluated. As a result, a moist feel to the skin after bathing was given. Component wt% Distearyldimethylammonium chloride 59.0 Palm oil fatty acid amide propyldimethylglycine 16.0 Dimethylmyristylamine oxide 4.0 Polyoxypropylene (0.5) myristic acid isopropanol amide mixture 7.0 Fragrance 1.0 ・ Remaining purified water

Example 97 A waterless hand cleaner having the following composition was prepared,
When its performance was evaluated, it showed good detergency. Component wt% Deodorized kerosene 20.0 Oleic acid 10.0 Methylcyclohexanol 2.0 Mixture of Example 8 4.5 POE (40) Lanolin alcohol 4.0 Hexylene glycol 4.5・ Potassium hydroxide 0.2 ・ Triethanolamine 3.2 ・ Perfume proper amount ・ Preservative proper amount ・ Purified water balance

Example 98 A dry cleaning detergent having the following composition was prepared and its performance was evaluated. Component wt% Alkylbenzene sulfonic acid dibutyl isopropanol amine salt 30.0 • Compound mixture of Example 6 15.0 • 2-Ethylhexyl sulfosuccinate 20.0 • Petroleum solvent 35.0

Example 99 A solid deodorant toilet bowl cleaner having the following composition to be used in a water tank was prepared and its performance was evaluated. As a result, excellent cleaning power was exhibited. Component wt% Polyethylene glycol 11000 47.0 Compound mixture of Example 3 30.0 Dye 3.0 Menthol 10.0 Geraniol 10.0

Example 100 A furniture polish having the following composition was prepared and its performance was evaluated. As a result, it was shown that the furniture wall surface had an excellent stain-removing ability and a gloss after use. Component % by weight • Polyoxypropylene (2) myristic acid isopropanol amide mixture 3.0 • Stearic acid 1.2 • Mineral seal oil 20.0 • Heavy mineral oil 20.0 • Purified water balance

Example 101 A solid car wash having the following composition was prepared and its performance was evaluated. As a result, it showed excellent detergency. Component wt% -coconut oil fatty acid monoethanolamide 53.0-polyethylene glycol 6000 20.0-Compound composition of Example 4 10.0-stearyltrimethylammonium chloride 8.0-liquid paraffin 5.0-silicone oil 2 .0 ・ Amine modified silicone oil 2.0

[0152]

EFFECTS OF THE INVENTION The polyoxypropylene fatty acid isopropanolamide mixture of the present invention is characterized by having a low melting point, good handling properties, being stable in a wide pH range, and having little irritation to the eye mucous membrane. Further, the compound of the present invention, when used in combination with other surfactants, has excellent thickening / foaming / foaming stability, so that it is easy to handle, has excellent low temperature stability, and has a wide range of properties. It can be used even at pH, and can be used as a safe thickener / foaming agent / foaming stabilizer with less irritation.
It has excellent dispersibility / solubilization power, so it is an emulsifier / dispersant.
It can be used as a solubilizer. Further, in the method for producing a polyoxypropylene fatty acid isopropanolamide of the present invention, a highly pure polyoxypropylene fatty acid isopropanolamide mixture can be produced without performing a purification step between steps or after the final step. According to the method of the present invention, a polyoxypropylene fatty acid isopropanolamide mixture can be easily produced industrially. Furthermore, by using the polyoxypropylene fatty acid isopropanolamide mixture of the present invention, it is possible to obtain a cosmetic composition which is excellent in emulsion stability and is also excellent in usability. Furthermore, the detergent composition containing the polyoxypropylene fatty acid isopropanolamide mixture of the present invention has less irritation to the skin, hair and eye mucous membrane, and further has improved foaming power / detergency / viscosity / foaming stability. And a low melting point makes it easy to prepare, and a detergent composition excellent in low-temperature stability can be provided.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical display location C07C 231/02 9547-4H C07C 231/02 233/20 9547-4H 233/20 C11D 1/52 C11D 1/52

Claims (11)

[Claims] 1. The following general formula (I): (However, in the formula (I), R represents a linear or branched saturated hydrocarbon or unsaturated hydrocarbon group having 7 to 21 carbon atoms, and PO
Represents an oxyalkylene group having 3 carbon atoms, and m is 0 or 1.
A mixture of two or more compounds represented by the above formula, wherein m of the compound of formula (I) in this mixture is
The average value of is a positive number of 0.3 to 20. Polyoxypropylene fatty acid isopropanolamide mixture. 2. The following general formula (II): (In the formula (II), R is the same as the above, and R ¹ has ¹ carbon atom.
Represents an alkyl group of 1 to 3. ) And a fatty acid alkyl ester represented by the chemical formula (III): The compound represented by the following general formula (IV): is reacted with isopropanolamine in the presence of a base catalyst. (Wherein R is the same as the above in the formula (IV)), a reaction mixture containing a fatty acid isopropanolamide represented by the formula (IV) contained in the reaction mixture without purification of the reaction mixture is prepared. To the compound of 0.3
The method for producing a polyoxypropylene fatty acid isopropanolamide mixture according to claim 1, characterized in that the addition reaction of ˜20 times mol of propylene oxide is carried out. 3. A thickener containing the polyoxypropylene fatty acid isopropanolamide mixture according to claim 1. 4. A foaming agent comprising the polyoxypropylene fatty acid isopropanolamide mixture according to claim 1. 5. A foam stabilizer comprising the polyoxypropylene fatty acid isopropanolamide mixture according to claim 1. 6. An emulsifier containing the polyoxypropylene fatty acid isopropanolamide mixture according to claim 1. 7. A dispersant containing the polyoxypropylene fatty acid isopropanolamide mixture according to claim 1. 8. A solubilizing agent comprising the polyoxypropylene fatty acid isopropanolamide mixture according to claim 1. 9. A cosmetic comprising the polyoxypropylene fatty acid isopropanolamide mixture according to claim 1. 10. A detergent composition comprising the polyoxypropylene fatty acid isopropanolamide mixture according to claim 1. 11. A mixture of the polyoxypropylene fatty acid isopropanolamide mixture according to claim 1 and at least one selected from anionic surfactants, cationic surfactants, amphoteric surfactants and nonionic surfactants. A cleaning composition comprising: