JPH10183168A - Detergent composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject composition which contains a specific amidoether carboxylate, a specific amidoether and a specific compound and is excellent in detergency and lathering power and gentle to the skin. SOLUTION: This composition contains (A) an amidoether carboxylate expressed by formula I [R is a 5-21C straight-chain or branched alkyl, etc.; (n) and (m) are each 0 to 20 to hold the relationship of 1<=(n+m)<=20; EO is oxyethylene; PO is oxypropylene; A is H, (EP)k (PO)j H ((k) and (j) are each 0 to 20 to hold the relationship of 1<=(k+j)<=20), etc.; M is an alkaline (earth) metal], (B) an amidoether expressed by formula II [B is H, (EO)k (PO)j H, etc.] in such an amount that the weight ratio A/B falls in the range of 0.1 to 100, and (C) 0.01 to 40wt.% of a mono-, di- or tri-glyceride alkoxylate expressed by formula III [X<1> , X<2> , X<3> are each hydrogen or a group expressed by formula IV (R<1> is a straight-chain or branched 7-21C alkyl, etc.); A is a 2-4C alkylene; (m), (n) and (p) are each a mean addition molecular number of alkylene oxide that are not 0 simultaneously].

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a detergent composition which gives a user a refreshing feel and has a mild effect on the skin.

[0002]

2. Description of the Related Art Today, with increasing awareness of human safety, people such as kitchen cleaners, clothing cleaners, house cleaners, hair cleaners and body cleaners have been developed. In cleaning agents that often touch the skin of the skin,
Various attempts have been made to mildly affect the skin.

For example, the pH of a detergent is 5 to 6 (weakly acidic).
And the pH of the skin is brought close to the pH of human skin so that the action on the skin is mild, or the main cleaning base to be mixed is changed to one having a mild action on the skin as much as possible.

[0004] As such a mild cleaning base,
In some cases, an amino acid surfactant or an alkyl phosphate surfactant is used (Japanese Patent Publication No. 50-4012).
No. 5, JP-B-55-90335, JP-B-58
-27319). However, although these surfactants are hypoallergenic, they alone do not always exhibit sufficient foaming power and detergency, and have disadvantages such as poor solubility and difficulty in obtaining a stable composition. Have.

In kitchen detergents, sodium alkylbenzenesulfonate has been widely known as a base having excellent detergency, but it is still insufficient in terms of mildness to the skin. It has a drawback that hand roughness is likely to occur due to the strength of degreasing and the like.

In order to solve these problems, kitchen cleaners containing sodium alkylethoxysulfate, which is less irritating to the skin, as a main cleaning base have recently become the mainstream. In this case, it is also known that by using a co-activator such as a tertiary amine oxide or a higher fatty acid diethanolamide in combination, various performances can be improved and the action on the skin becomes milder.

However, although the effects of various cleansing agents on the skin are milder than in the past, the fact is that they have not yet reached a satisfactory level. Further, all of these activators have a strong feeling of nullness at the time of use, and it is hard to say that the use feeling is always necessarily good.

On the other hand, alkyl glycosides, which are sugar derivative surfactants, are known as low-irritant surfactants, and produce stable and rich foams in spite of being nonionic surfactants. I do. For example, JP-A-58-1
Japanese Patent No. 04625 describes a foaming surfactant composition containing an alkyl glycoside and an anionic / amphoteric surfactant, and JP-A-58-186429 discloses an alkyl glycoside, an anionic / amphoteric surfactant. Foaming surfactant compositions containing an agent and an amide / amine oxide are described. JP-A-64-69695 describes a detergent composition containing a specific ratio of an alkyl glycoside and an amphoteric surfactant.

[0009] However, the surfactant composition and the detergent composition described in these publications are superior to conventional polyoxyethylene alkyl ether-based detergents in various properties, but are not suitable for the skin. The level of mildness has not yet reached a satisfactory level. In particular, for alkyl glycosides, alkylbenzenesulfonic acid, α-olefinsulfonic acid salt,
When a sulfate group such as an alkyl sulfate, an alkyl ethoxy sulfate, or an α-sulfofatty acid ester salt, or an anionic surfactant having a sulfonate group is used in combination, from the viewpoints of detergency, foaming power, or economy, Although preferred, mildness to the skin and a reduction in the feeling of use were inevitable problems. Such a decrease in mildness to the skin is considered to be caused by an increase in denaturing action on proteins constituting the skin, and has been a problem for some time.

On the other hand, amide ether carboxylate is known as a mild surfactant like alkylglycoside, and is commercially available from CHEM-Y of Germany under the trade name of AKIPO. However, the amide ether carboxylate alone has a problem that the foaming power is poor.

Techniques known for the application of such a surfactant to a detergent include amide ether carboxylic acid and polyoxyethylene alkyl sulfate, fatty acid diethanolamide, higher alcohol alkylene oxide adduct, acyl Detergent containing sarcosinate and the like (European Patent No. 102118), a method of using an amide ether carboxylic acid-based surfactant and a polyoxyethylene alkyl sulfate (European Patent No. 215504), and oils and fats as starting materials Foam bath agent in which amide ether carboxylic acid and lauryl sulfate, lauryl ether sulfate, alkyl ether carboxylic acid, quaternary compound obtained by reacting lauric acid with glycidyltrimethylammonium chloride, A cleaning agent containing a soap, a amide ether carboxylic acid or an alkyl ether carboxylate as a main component, and a cleaning agent (US Pat. No. 4,865,575). Specification) and the like.

As a technique for compensating for the drawback that the foaming power is weak, a technique in which the content of a glycerin derivative is suppressed to a low level as a composition and further combined with various surfactants has been proposed (Japanese Patent Application Laid-Open No. Hei 8-27481). JP-A-8-100193, JP-A-8-104888, JP-A-8-104889, JP-A-7-13
No. 8592) and the like.

However, even with these techniques relating to amide ether carboxylic acids, it has still been difficult to sufficiently achieve both sufficient detergency and improved skin feel. Therefore, an object of the present invention is to provide a detergent composition having sufficient detergency and foaming power, and having a high mild feeling on the skin.

[0014]

Means for Solving the Problems The present inventors have focused on the mildness of the amide ether carboxylate to the skin and its cleansing performance, and as a result of intensive studies, as a result, by combining a specific glyceride alkoxylate, It has been found that the object can be achieved. Furthermore, surprisingly, they have found that the present invention can provide a lighter touch than ever before, and have completed the present invention.

That is, the present invention provides the following (a), (b) and (c)
The component (a) / (b) has a weight ratio [(a) / (b)] of 0.1 to 100, and the content of the component (c) in the whole composition Is in the range of 0.01 to 40% by weight. (a) An amide ether carboxylate represented by the following general formula (I).

[0016]

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Wherein R represents a linear or branched alkyl or alkenyl group having 5 to 21 carbon atoms, and n and m are
The numbers 0 to 20 satisfying 1 ≦ n + m ≦ 20 are indicated,
EO represents an oxyethylene group, PO represents an oxypropylene group, and A represents (EO) _k (PO) _j CH ₂ COOM, (EO) _k (PO) _j H, a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. (Where k and
j represents a number from 0 to 20 that satisfies 1 ≦ k + j ≦ 20. ), M represents an alkali metal, alkaline earth metal, amine or alkanolamine. (B) An amide ether represented by the following general formula (II).

[0018]

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Wherein B is (EO) _k (PO) _j H, a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R, n, m, k, E
O, PO and j are the same as those shown in the general formula (I). R between the above general formulas (I) and (II)
, N, m, k and j may be the same or different. (C) the following general formula (III)

[0020]

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[Wherein X ¹ , X ² , X ³ : the same or different,

[0022]

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And a hydrogen atom or a group represented by here
R ¹ represents a linear or branched alkyl or alkenyl group having 7 to 21 carbon atoms. A: represents an alkylene group having 2 to 4 carbon atoms, and (m + n + p) A may be the same or different. m, n, p: The same or different, and is a number from 0 to 10 indicating the average addition mole number of the alkylene oxide. Where m, n,
p cannot be 0 at the same time. A glyceride alkoxylates represented by], in the general formula ^{(III), X 1, X} 2, the content of X ³ things are all hydrogen atoms is 0 to 4 ^{wt%, X 1, X 2,} X 2 of the ^three are hydrogen atoms, the remainder formula

[0024]

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[Wherein, R ¹ has the above-mentioned meaning. The content of the group represented by the formula ( ¹ ) is 0 to 10% by weight, and X ¹ , X ² , X ³
One of which is a hydrogen atom and the rest of the formula

[0026]

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[In the formula, R ¹ has the meaning described above. The content of the group represented by the formula ( ¹ ) is 0 to 40% by weight, X ¹ , X ² , X ³
Are all expressions

[0028]

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[Wherein, R ¹ has the meaning described above. A glyceride alkoxylate having a content of a group represented by the formula:

[0030]

Embodiments of the present invention will be described below in detail.

The amide ether carboxylate represented by the above general formula (I), which is the component (a) used in the present invention, is used for improving mildness on skin.

In the above formula (I), the alkyl group or alkenyl group represented by R is preferably an alkyl group, particularly a straight-chain alkyl group. 9-17, especially 10-14 are preferred. Also, n is 1 to 7 in terms of foaming property, and further 2 to 2
5, especially 2-3 are preferred. Further, m is preferably 0 to 5, more preferably 0 to 2, and particularly preferably 0 in terms of foaming property.
A is preferably a hydrogen atom from the viewpoint of foaming properties. K in the group represented by A is preferably 0 to 5 in terms of foaming property, and j is 0 to 2, particularly 0 in terms of foaming property.
Are preferred.

The cations represented by M include alkali metal ions such as sodium and potassium; alkaline earth metal ions such as magnesium and calcium; ammonium ions; monoethanolammonium (HOCH ₂ CH ₂ N
H ^3+), diethanolammonium _{[(HOCH 2 CH 2) 2} NH 2 +],
Preferably alkanolammonium ions such as triethanolammonium _{[(HOCH 2 CH 2) 3} NH +], among them the alkali metal ions, preferably alkali earth metal ion, sodium ion, magnesium ion are more preferable.

The content of the component (a) is preferably 3 to 70% by weight, more preferably 5 to 40% by weight in the composition of the present invention. When the content is 3% by weight or more, sufficient foaming power can be obtained. When the content is 70% by weight or less, the composition can be easily produced. Solution stability can be obtained.

The amide ether represented by the general formula (II), which is the component (b) used in the present invention, is used as a foaming agent.

In the general formula (II), the alkyl group or alkenyl group represented by R is preferably an alkyl group, particularly a straight-chain alkyl group, and more preferably has 9 carbon atoms from the viewpoints of solubility, foamability and detergency. To 17, especially 10 to 14 are preferred. Further, n is preferably 1 to 7, particularly preferably 2 to 5 in terms of foaming property. Further, m is 0 to 5 in terms of foaming property, and further 0 to 0.
2, especially 0 is preferred. B is particularly preferably a hydrogen atom from the viewpoint of foaming properties. K in the group represented by B
Is preferably 0 to 5, particularly preferably 0 to 2 in terms of foaming property,
j is preferably from 0 to 2, particularly preferably 0, from the viewpoint of foaming properties.

The content of the component (b) in the composition of the present invention is preferably 1 to 70% by weight, more preferably 3 to 40% by weight. When the content is 1% by weight or more, a sufficient foaming power can be obtained. When the content is 70% by weight or less, the composition can be easily produced. Solution stability can be obtained.

The weight ratio [(a) / (b)] of the content of the component (a) to the content of the component (b) is 0.1 to 100, preferably 0.1 to 20, more preferably 0.1 to 20. -10, most preferably 0.5-3. If the above weight ratio is less than 0.1, the mildness to the skin is impaired, causing nulling,
On the other hand, if it exceeds 100, the foaming power is insufficient, which is not preferable.

The total content of the components (a) and (b) is preferably from 1 to 80% by weight, more preferably from 5 to 40% by weight. By making the total content 1% by weight or more, sufficient foaming power can be obtained, and 80% by weight.
The following makes the composition easy to produce, and in the case of a liquid detergent, sufficient solution stability can be obtained.

The amide ether carboxylate (hereinafter referred to as "amide ether carboxylate (a)") as the component (a) used in the present invention is produced, for example, by the method described in European Patent No. 2 198 93. can do. The method for producing a mixture of the component (a) and the component (b) (hereinafter, referred to as an “amide ether derivative mixture”) is not particularly limited, and the amide ether (hereinafter, referred to as the component (b)) Amide ether (b) '') can be directly produced by reacting halogen acetic acid, or the amide ether (b) can be post-added to the amide ether carboxylate (a). .

As a method for synthesizing the amide ether (b), which is an intermediate for producing the amide ether carboxylate (a), an alkanolamine is reacted by using a lower alkyl ester of a fatty acid such as a fatty acid methyl ester as a starting material, Then, a polyoxyethylenation and / or polyoxypropylene conversion method, a method of reacting an alkanolamine using fats and oils as a starting material, and then a polyoxyethylenation and / or polyoxypropylene conversion method, and a reaction of an alkanolamine using a fatty acid as a starting material And then polyoxyethylenation and / or polyoxypropylene conversion. Among these, a method of producing a fatty acid lower alkyl ester such as a fatty acid methyl ester as a starting material is preferable because it is less colored and substantially does not contain glycerin or a glycerin derivative as an impurity.

Other methods for synthesizing the amide ether (b), for example, starting from fats and oils having a coconut oil fatty acid composition,
In the method of polyoxyethylenation and / or polyoxypropylene conversion after reacting a linear alkanolamine, glycerin represented by the following general formula (IV) or glyceryl ether having an average molecular weight of less than 300 derived from fats and oils is used. A large amount is formed, and the yield of the component (b) and, thus, the component (a) is low, which is not practically preferable. In the above method for producing an amide ether derivative mixture, the ratio between the amide ether carboxylate (a) and the amide ether (b) in the obtained amide ether derivative mixture is such that the amide ether (b) is converted to an alkali monohaloacetic acid salt. The reaction can be adjusted by selecting the reaction conditions such as the molar ratio and the mixing method in the reaction.

[0043]

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Wherein R ² is a hydrogen atom,-(EO) _r (PO) _s CH ₂ CO
OM or-(EO) _t (PO) _u H, wherein three R ² in the same molecule may be the same or different (here, EO represents an oxyethylene group, PO represents an oxypropylene group, r , S,
t and u are numbers satisfying the following equation. 1 ≦ r + s ≦ 2
0, 1 ≦ t + u ≦ 20). M represents a hydrogen atom, an alkali metal, an alkaline earth metal, an amine or an alkanolamine. ].

In the cleaning composition of the present invention, the formula (IV)
The content of glycerin or glyceryl ether having a weight average molecular weight of less than 300 represented by
(b) It is preferable that the content is 10% by weight or less, particularly 5% by weight or less, more preferably 0% by weight (substantially not contained) based on the total content of the components. By setting the content to 10% by weight or less, sufficient foaming power can be obtained. Therefore, for example, using a fat or oil of coconut oil fatty acid composition as a starting material,
When amide ether (b) is synthesized by directly reacting alkanolamine and then polyoxyethylenating and / or polyoxypropylene, glyceryl ether represented by general formula (IV) derived from fats and oils is produced. ,
Not preferred.

As the amide ether carboxylate as the component (a), there is, for example, one which is commercially available from CHEM-Y of Germany under the trade name of "Akipo".
Since it contains glycerin represented by the above general formula (IV) or glyceryl ether having a weight average molecular weight of less than 300 due to its production method, it is not preferable to use it for the purpose of the present invention.

The component (c) of the present invention is a glyceride alkoxylate represented by the aforementioned general formula (III), wherein the proportion of mono-, di-, and tri-glyceride alkoxylates is within a specific range. Rate.

In the general formula (III), R ¹ has 7 to 21 carbon atoms.
Means a linear or branched alkyl or alkenyl group of the formula

[0049]

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As the group represented by, an acyl group derived from soybean oil is preferable. That is, when the composition of the acyl group is such that C ₁₆ F ₀ is 10
By weight%, C ₁₈ F ₀ is 4 wt%, C ₁₈ F ₁ 24 wt%, C ₁₈ F ₂
Is preferably 54% by weight and C ₁₈ F ₃ is 8% by weight.
Here, F ₀ means no unsaturated group, F ₁ means having one unsaturated group, F ₂ means having two unsaturated groups, and F ₃ means _three unsaturated groups. Means having

In the general formula (III), examples of AO include oxyalkylene groups having 2 to 4 carbon atoms, and oxyethylene and oxypropylene groups are particularly preferred. The (m + n + p) AOs may be the same or different. m, n, and p are numbers of 0 to 10 indicating the average number of moles of alkylene oxide added, and these are not simultaneously 0. The total number of moles of alkylene oxide added,
That is, m + n + p is more than 0 and 30 or less, preferably 3 to 10, and particularly preferably 5 to 7 from the viewpoint of performance.

The glyceride alkoxylate of the present invention has a glycerin alkoxylate content in which X ¹ , X ² , and X ³ are all hydrogen atoms in the general formula (III).
% By weight, and particularly preferably 0 to 2% by weight. ^{Two of} X ¹ , X ² , and X ³ are hydrogen atoms, and the rest are of the formula

[0053]

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It is necessary that the content of the monoglyceride alkoxylate, which is a group represented by the formula, be 0 to 10% by weight, and particularly preferably 0 to 7% by weight. X ¹ , X ² ,
One of X ³ is a hydrogen atom and the rest are

[0055]

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It is necessary that the content of the diglyceride alkoxylate, which is a group represented by the formula, be 0 to 40% by weight, and particularly preferably 0 to 25% by weight. Further, all of X ¹ , X ² , and X ³ are formulas

[0057]

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It is necessary that the content of triglyceride alkoxylate, which is a group represented by the formula, is 50% by weight or more, and particularly preferably 70 to 100% by weight. A glyceride alkoxylate satisfying such conditions is extremely excellent in emulsifying ability, foaming, and skin feel after use.

The glyceride alkoxylate as the component (c) of the present invention can be prepared by, for example, adding trialkylglyceride to an alkylene oxide having 2 to 4 carbon atoms (hereinafter referred to as AO) in the presence of an alkoxylation catalyst. AO with 2 to 4 carbon atoms in a mixture of a small amount of glycerin
A method of reacting glycerin with AO having 2 to 4 carbon atoms to cause a transesterification reaction between the obtained compound and a fatty acid lower ester, and a method of reacting glycerin with AO having 2 to 4 carbon atoms to obtain a compound obtained. And a fatty acid by an esterification reaction or the like. In any case, it is necessary that the ratio of the mono-, di- and tri-forms is within the range specified above.

In addition to the above-mentioned essential components, a known activator for a detergent can be appropriately added to the detergent composition of the present invention, if necessary, for the purpose of improving the detergency and foaming power. .

Examples of the activator that can be added include a nonionic activator, an anionic activator and an amphoteric activator. Specific examples of the nonionic activator include, for example, polyoxyethylene (average number of moles of 4 to 20). Alkyl (C8-C22
Linear or branched chain) ethers, mono- or dialkanol (C 2-3) amides of higher fatty acids having 4 to 22 carbon atoms,
Tertiary alkyl (linear or branched chain having 8 to 22 carbon atoms) amine oxide, alkyl (linear or branched chain having 8 to 18 carbon atoms) glyceryl ether, alkyl (linear or branched chain having 8 to 18 carbon atoms) ) Glycosides and the like, among which alkylglycosides are preferred.

Further, specific examples of the anionic activator include:
α-olefin (C8-22) sulfonate, polyoxyethylene (average addition number 2-8) alkyl (C8-22 straight or branched chain) sulfate, α-sulfofatty acid ester N-acyl (8-18 carbon atoms) glutamate, monoalkyl (8-18 carbon atoms) phosphate,
Linear alkyl (C18-C18) benzenesulfonate,
Alkyl (C8-18) ether (average number of moles added 2)
To 10) Carboxylates and the like. At this time, as the counter ion, Na, K, Mg, triethanolamine, ammonium and the like are preferable.

Examples of the amphoteric activator include alkyl betaine, alkyl sulfo betaine, amido betaine and the like.

The pH range of the stock solution of the cleaning composition of the present invention is preferably from 4 to 10, and more preferably from 6 to 8. Further, other optional components can be added to the cleaning composition of the present invention as long as the separation stability and cleaning performance of the composition are not impaired. For example, lower aliphatic alcohols such as ethyl alcohol, toluene sulfonic acid and xylene sulfonic acid, sodium and potassium salts of benzoic acid, hydrotropic agents such as urea, viscosity modifiers such as clay minerals and water-soluble polymers, silica stone Water-insoluble abrasives such as calcium phosphate, zeolite, calcium carbonate, polyethylene, nylon, and polystyrene; humectants such as polyethylene glycol and sorbitol; feel-improving agents such as cellulose derivatives;
Flavors, pigments, enzymes, bleaching agents, and further, preservatives and fungicides can be added as appropriate.

The composition of the present invention is prepared by mixing the essential components (a), (b) and (c), and, if necessary, known activators and other optional components according to a conventional method. An aqueous solution is obtained by adding water to the solution [usually, depending on the purpose, an active ingredient (a component other than water) is selected from a concentration of 5 to 80% by weight].
It is prepared as

The cleaning composition of the present invention can be used for various cleaning compositions such as a kitchen cleaning composition, a clothing cleaning composition, a home cleaning composition, a hair cleaning composition, and a body cleaning composition. Although it can be used for applications, it is particularly preferable to use it as a kitchen detergent composition, a hair detergent composition, particularly a kitchen detergent composition.

[0067]

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

The production methods and physical properties of glyceride alkoxylates 1 to 4 used in the following examples are shown below.

Synthesis Example 1 <Synthesis of glyceride alkoxylates 1 and 3> 952.2 g (1.1 mol) of soybean oil and 19.08 g of MgO—Sb ₂ O ₃ catalyst
(2% with respect to soybean oil) was charged into a 3.5 liter autoclave, and the temperature was raised to 165 ° C. after nitrogen substitution. At the same temperature, 148 g (3.36 mol) of ethylene oxide was added to 3 to 5 kg / cm ² G
The pressure was maintained for 7 hours and 35 minutes. After further aging for 7 hours and 20 minutes, the mixture was cooled to 80 ° C.
After extracting 3.7 g, deaerated at 80 ° C. under reduced pressure, the catalyst was removed by filtration under pressure at a nitrogen pressure of 3 kg / cm ² G to obtain soybean oil 3 mol ethoxylate (glyceride alkoxylate 1). ).

On the other hand, the reactants remaining in the autoclave are:
The temperature was raised again to 165 ° C, and 56 g of ethylene oxide (1.27
Mol) at the same temperature and at a pressure of 3 to 5 kg / cm ² G.
Minutes, then aged at the same temperature for 12 hours 30 minutes, 80
After cooling to 80 ° C., 270.5 g of the reaction product was extracted, degassed at 80 ° C. under reduced pressure, and the catalyst was removed by filtration under nitrogen pressure of 3 kg / cm ² G to obtain 5 mol ethoxylate of soybean oil. (Glyceride alkoxylate 3).

Synthesis Example 2 <Synthesis of Glyceride Alkoxylates 2 and 4> (1) Synthesis of Glycerin Ethoxylate In a 5 liter autoclave, 972.0 g of glycerin (1
(0.55 mol) and 5.91 g (0.105 mol) of potassium hydroxide, and dehydrated at 110 ° C. at 28 Torr for 30 minutes. 155 ° C
Temperature up to 1395 g (31.67 mol) of ethylene oxide
Was charged over 1 hour and 15 minutes. Aging was performed at the same temperature for 30 minutes. After cooling to 90 ° C, 1193 g of the reactant was withdrawn,
Deaeration was performed at 80 ° C. under reduced pressure to obtain glycerin 3 mol ethoxylate. On the other hand, the reactant remaining in the autoclave is
After the temperature was raised to 55 ° C., 462 g (10.5 mol) of ethylene oxide was charged over 45 minutes. After aging at the same temperature for 30 minutes, the mixture was cooled to 90 ° C., 931.9 g of the reaction product was extracted, and deaerated at 80 ° C. under reduced pressure to obtain glycerin 5 mol ethoxylate.

(2) <Glyceride alkoxylate 2
Synthesis of Soybean Oil> 389.2 g (1.33 mol) of fatty acid methyl ester of the soybean oil composition, 100 g (0.44 mol) of 3 mol ethoxylate of glycerin obtained in the previous step (1), and 2.4 g (0.044 mol) of sodium methylate The reaction was allowed to proceed for 5 hours at a temperature range of 75 to 112 ° C and a vacuum of 42 to 30 Torr while removing methanol to obtain 3 mol ethoxylate of soybean oil (referred to as glyceride alkoxylate 2).

(3) <Glyceride alkoxylate 4
Synthesis of Soybean Oil Fatty Acid Methyl Ester 342.4 g (1.
17 mol), 120 g (0.39 mol) of 5 mol ethoxylate of glycerin obtained in the previous step (1), and 2.0 g (0.037 mol) of sodium methylate, and a vacuum of 30 Torr at a temperature range of 78 to 117 ° C. The reaction was allowed to proceed for 4.5 hours while removing methanol to obtain 5 mol ethoxylate of soybean oil.

Table 1 shows the oil and fat analysis values of the glyceride alkoxylates 1 to 4 synthesized as described above. In addition, glycerin ethoxylate, monoalkyl form, dialkyl form,
Table 2 shows the area% of the trialkyl compound.

[0075]

[Table 1]

[0076]

[Table 2]

Example 1 Detergent compositions having the compositions shown in Tables 3 and 4 below were prepared and evaluated for detergency, feeling of use, and roughness by the following evaluation methods. The results are shown in Tables 3 and 4.

(Test Method and Evaluation Criteria) (1) Detergency Test Sudan III (red dye) was added to beef tallow as an indicator at 0.1% by weight.
Add 2.5 g of this to a porcelain dish (25 cm diameter). This is mixed with 3 g of the detergent composition and water (hardness 3.5 degrees DH).
Of the dishes that were washed with a sponge impregnated with 27 g of water at 40 ° C. until no more tallow was removed from the dishes.

(2) Usability test A detergent aqueous solution having a detergent composition concentration of 5% by weight (water hardness of 3.5%).
(Degree DH, 40 ° C.). One liter of this aqueous detergent solution is placed in a 2 liter beaker, and hands are immersed in the aqueous solution. At this time, the feel of the hands in the detergent aqueous solution was evaluated by five expert panelists according to the following criteria, and the average was shown. In this test, it is desirable that the average score be 2 or less. Evaluation criteria Very slimy; 4 Slightly slim; 3 Slightly refreshing; 2 Very refreshing;

(3) Hand Roughness Test A detergent solution having a detergent composition concentration of 5% was prepared, and the solution temperature was adjusted to 30 ° C.
Keep your hands immersed in your hands for 20 minutes every day, then wash well with water. This operation is repeated for three days. Four days later, the state of the hands of the five subjects was visually determined according to the following criteria, and indicated by an average score.
In this test, it is desirable that the average score be 4 or more. 5 points: Hand roughness is not recognized. 4 points: Hand roughness is slightly observed. 3 points: Hand roughening is slightly observed. 2 points: Hand roughness is considerably recognized. 1 point: Hand roughness is remarkably recognized.

[0081]

[Table 3]

[0082]

[Table 4]

Claims (3)

[Claims] (1) The composition contains the following components (a), (b) and (c),
The weight ratio of the content of the component (a) to the content of the component (b) [(a) /
(b)] is 0.1 to 100, and the content of the component (c) in the whole composition is in the range of 0.01 to 40% by weight. (a) An amide ether carboxylate represented by the following general formula (I). Embedded image [Wherein, R represents a linear or branched alkyl or alkenyl group having 5 to 21 carbon atoms, and n and m represent 1 ≦ n + m ≦
Each represents a number from 0 to 20 that satisfies 20, EO represents an oxyethylene group, PO represents an oxypropylene group, and A represents (EO)
_k (PO) _j CH ₂ COOM, (EO) _k (PO) _j H, hydrogen atom or carbon number 1
And 3 to 3 (where k and j are 1 ≦ k +
The numbers 0 to 20 satisfying j ≦ 20 are shown. ), M represents an alkali metal, alkaline earth metal, amine or alkanolamine. (B) An amide ether represented by the following general formula (II). Embedded image Wherein B is (EO) _k (PO) _j H, a hydrogen atom or 1 to 3 carbon atoms.
Wherein R, n, m, k, EO, PO and j are the same as those represented by the above formula (I). R, n, m, k and j in the above general formulas (I) and (II) may be the same or different. (C) the following general formula (III): [Wherein, X ¹ , X ² , X ^{3 are the} same or different, and have the formula: Represents a group represented by or a hydrogen atom. Here, R ¹ represents a linear or branched alkyl group or alkenyl group having 7 to 21 carbon atoms. A: represents an alkylene group having 2 to 4 carbon atoms, and (m + n + p) A may be the same or different. m, n, p: The same or different, and is a number from 0 to 10 indicating the average addition mole number of the alkylene oxide. Where m, n,
p cannot be 0 at the same time. A glyceride alkoxylates represented by], in the general formula ^{(III), X 1, X} 2, the content of X ³ things are all hydrogen atoms is 0 to 4 ^{wt%, X 1, X 2,} X two of the ³ are hydrogen atoms, the remainder formula: 5] [Wherein, R ¹ has the above-mentioned meaning. The content of the group represented by the formula ( ¹ ) is 0 to 10% by weight, ^one of X ¹ , X ² and X ³ is a hydrogen atom, and the remainder is of the formula: [Wherein, R ¹ has the above-mentioned meaning. The content of the group represented by the formula is 0 to 40% by weight, and X ¹ , X ² and X ³ are all represented by the formula [Wherein, R ¹ has the above-mentioned meaning. A glyceride alkoxylate having a content of a group represented by the formula: 2. The content of glycerin represented by the following general formula (IV) or glyceryl ether having a weight average molecular weight of less than 300 is 10% with respect to the total content of the components (a) and (b).
%. Embedded image Wherein R ² is a hydrogen atom,-(EO) _r (PO) _s CH ₂ COOM or-(EO)
_t (PO) _u H, wherein three R ² in the same molecule may be the same or different (here, EO is an oxyethylene group,
PO represents an oxypropylene group, and r, s, t and u each represent a number satisfying the following formula. 1 ≦ r + s ≦ 20, 1 ≦ t + u
≦ 20). M represents a hydrogen atom, an alkali metal, an alkaline earth metal, an amine or an alkanolamine. ] 3. The glyceride alkoxylate of the component (c), which has the formula: The cleaning composition according to claim 1 or 2, wherein the group represented by is an acyl group derived from soybean oil.