JPH09278892A - (poly)glycerin ester-modified organo(poly)siloxane, its production, and detergent composition containing it - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a (poly)glycerin ester-modified organo(poly)siloxane which is excellent in detergency and feel to the touch and is useful as a compounding ingredient for a detergent by selecting a specific modified organo(poly)siloxane. SOLUTION: This (poly)glycerin ester-modified organo(poly)siloxane has at least one silicon atom modified by a group represented by formula I (wherein R<1> is a 2-22C alkylene; and (m) is 1-30), is pref. exemplified by a compd. represented by formula II (wherein R<2> to R<6> are each a 1-22C alkyl, alkoxy, or phenyl; at least one group selected from among X, n Y's, and Z is group represented by formula I, and rest being each a 1-22C alkyl, or phenyl; and (n) is 0-1,000), and is obtd. by reacting an organo(poly)siloxane having at least one silicon-bonded hydrogen atom with a terminally unsatd. (poly)glycerin ester compd. represented by formula III (wherein R<1> ' is a single bond or a 1-20C alkylene).

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention contains a (poly) glycerin ester-modified organo (poly) siloxane useful as a cleansing agent for skin or hair, etc., a process for producing the same and a compound containing the compound, and is excellent in detergency and feel. Detergent composition.

[0002]

2. Description of the Related Art Silicone is known to have a high bond energy in the main chain and excellent heat resistance, acid resistance, weather resistance, etc., low surface tension, release properties, lubricity and water repellency. There is. Furthermore, since the intermolecular force is small, the main chain is flexible and has high gas permeability, and physiologically inert, it has low toxicity,
It also has the characteristic of being hypoallergenic. For these reasons, silicone has traditionally been used in electrical, electronic, automobile, mechanical, medical,
It is used in a wide range of fields such as cosmetics, textiles, paper, pulp, and building materials.

[0003] In particular, in the field of cosmetics and cosmetics,
The application of dimethylpolysiloxane and cyclic silicone, which are not sticky and highly safe, as hair finishing agents and as oils in cosmetics has been studied. In order to meet such applications, organo (poly) siloxanes are required to have further improved compatibility, chemical resistance, water solubility, lubricity and the like.

To meet these requirements, modified organopolysiloxanes having various functional groups introduced therein, such as amino modified, epoxy modified, carboxylic acid modified, mercapto modified, alcohol modified, polyether modified, and fluoroalkyl modified. , Alkyl-modified, ester-modified and alkoxy-modified organopolysiloxanes have been studied and developed.

[0005]

However, a modified organopolysiloxane which is sufficiently satisfactory as a blending component of a detergent, especially a detergent for skin or hair, has not yet been obtained, and various conventional modified organopolysiloxanes have not been obtained. The detergency and feel were not sufficient, and it was not suitable for practical use.

Accordingly, it is an object of the present invention to provide a modified organo (poly) siloxane which is excellent in detergency and feel and is useful as a blending component of a detergent, and a method for producing the same.

[0007]

Under these circumstances, the inventors of the present invention have conducted extensive studies to solve the above-mentioned problems, and as a result, organo (poly) siloxane modified with a specific ester compound has excellent detergency and touch. It has been found that it is extremely useful as a blending component of a detergent, and has completed the present invention.

That is, according to the present invention, at least one silicon atom of the organo (poly) siloxane is represented by the following general formula (1):

[0009]

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[In the formula, R ¹ represents a linear or branched alkylene group having 2 to 22 carbon atoms, and m represents a number of 1 to 30. ] A (poly) glycerin ester-modified organo (poly) siloxane modified by a group represented by the following, a method for producing the same, and a detergent composition containing the same are provided.

In the present invention, "organo (poly)"
By "siloxane" is meant to include any of high molecular weight organopolysiloxanes to low molecular weight organosiloxanes.

[0012]

BEST MODE FOR CARRYING OUT THE INVENTION In the general formula (1) representing a (poly) glycerin ester group for modifying a silicon atom of an organo (poly) siloxane, the number of carbon atoms represented by R ¹ is 2 to 2
As the linear or branched alkylene group of 2, ethylene,
Propylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, decamethylene, undecamethylene, dodecamethylene, tridecamethylene, tetradecamethylene, pentadecamethylene, hexadecamethylene group and the like can be mentioned. . Of these, a linear alkylene group having 4 to 12 carbon atoms, particularly 8 to 12 carbon atoms is preferable.

In the general formula (1), m represents a number of 1 to 30, and preferably 3 to 20, particularly 5 to 15.

Among the (poly) glycerin ester-modified organo (poly) siloxanes of the present invention, those represented by the following general formula (2) are preferred.

[0015]

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[Wherein R ^{2 to} R ⁶ are the same or different,
Each represents an alkyl group, an alkoxyl group or a phenyl group having 1 to 22 carbon atoms, at least one of X and n Y and Z is a group represented by the general formula (1), and the remainder is 1 to 22 carbon atoms. Represents an alkyl group, an alkoxyl group, or a phenyl group, and n represents a number of 0 to 1000. ]

In the general formula (2), R ^{2 to} R ⁶ and carbon atoms in X, Y and Z other than the group (1) are 1 to 22.
Examples of the alkyl group include a methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, heptyl, octyl, nonyl group and the like,
Examples of the alkoxyl group having 1 to 22 carbon atoms include methoxyl, ethoxyl, propoxyl, butoxyl, pentyloxyl, hexyloxyl, heptyloxyl,
Examples thereof include octyloxyl and nonyloxyl groups.
As X, Y and Z other than R ^{2 to} R ^{6 and the} group (1), an alkyl group and an alkoxyl group having 1 to 6 carbon atoms, particularly a methyl group, are preferable, and all of them are preferably a methyl group.

In the general formula (2), n is 0 to 1
The number of 000 is shown, but the number of 0 to 300, particularly 0 to 30, is preferable.

The (poly) glycerin ester-modified organo (poly) siloxane of the present invention is obtained, for example, by adding an organo (poly) siloxane having at least one hydrogen atom bonded to a silicon atom to a terminal represented by the following general formula (3). It can be produced by reacting an unsaturated (poly) glycerin ester compound.

[0020]

[Chemical 6]

[In the formula, R ¹ ′ is the above R ¹ excluding terminal ethylene and represents a single bond or a linear or branched alkylene group having 1 to 20 carbon atoms, and m has the same meaning as above. Indicates. ]

The organo (poly) siloxane used as a raw material in the production method of the present invention has the following general formulas (4) to (6).

[0023]

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[In the formula (4), R ^{2 to} R ⁶ and n have the same meanings as described above, and at least one of X ′, n Y ′ and Z ′ is a hydrogen atom, and the remainder is an alkyl group, An alkoxyl group or a phenyl group is shown. In the formula (5), R ⁷ represents an alkyl group, an alkoxyl group, or a phenyl group, and r number of Y ″
Represents at least one hydrogen atom, and the remainder represents an alkyl group, an alkoxyl group or a phenyl group, and r represents 3 to 100.
(Preferably 3 to 10). In the formula (6), R ⁸
To R ¹⁸ are the same or different and each represents an alkyl group, an alkoxyl group or a phenyl group. s, t and u are 1 to 1000
And v represents a number from 0 to 1000. In each formula, R ² ~
Among ^{R 6, R 7, R 8} ~R 18, preferably has 1 to 22 carbon atoms as the alkyl group and the alkoxyl group further methyl group, methoxyl group and ethoxyl group, especially a methyl group. ] What is represented by these is mentioned, Especially what is represented by General formula (4) is preferable.

Specific examples of these organo (poly) siloxanes include, for example, 1,3,5,7,9-pentamethylcyclopentasiloxane, 1,3,5,7-tetramethylcyclotetrasiloxane, 1, 1, 1, 3, 5,
7,7,7-octamethyltetrasiloxane, tris (trimethylsiloxy) silane, 1,1,3,3,5
5-hexamethyltrisiloxane, 1,1,1,3
5,5,5-heptamethyltrisiloxane, pentamethyldisiloxane, 1,1,3,3-tetramethyldisiloxane, 1,3-diphenyl-1,3-dimethyldisiloxane, 1,1,1,3 , 3,5,5-heptamethyltrisiloxane, 1,1,3,3,5,5,7,7-octamethyltetrasiloxane and the like.

In the present invention, such an organo (poly) is used.
Siloxane may be produced by a known method, but a commercially available product may be used as it is, and specific examples thereof include TSF484, TSF483, XF40-A2606,
Examples include XF40-A1629, XF40-A5149, XF40-A2484 (above, manufactured by Toshiba Silicone Co., Ltd.).

The terminal unsaturated (poly) glycerin ester compound (3) used in the production method of the present invention can be produced, for example, according to the reaction formula shown below.

[0028]

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[In the formula, R ¹ ′, R ² and m have the same meanings as described above, and X represents a hydroxyl group, an alkoxyl group having 1 to 3 carbon atoms or a chlorine atom. ]

That is, first, the compound represented by the general formula (7) and the compound represented by the general formula (8) are mixed in a solvent such as benzene, hexane, toluene, xylene, or in the absence of a solvent, The reaction is carried out at 60 to 250 ° C. for 2 to 12 hours in the presence or absence of a catalyst such as p-toluenesulfonic acid, sulfuric acid, magnesium hydroxide and calcium hydroxide. The amount of each compound used is 1 to 4 times mol, particularly 1 to 2 times, of the compound represented by the formula (8) with respect to the compound represented by the formula (8).
It is preferably twice the molar amount. After completion of the reaction, the reaction solution is washed with a weakly acidic aqueous solution, a weakly alkaline aqueous solution, ion-exchanged water, or the like, if necessary, and further purified by distillation to obtain the compound represented by the formula (3).

To carry out the production method of the present invention, an organo (poly) siloxane having at least one hydrogen atom bonded to a silicon atom and a terminal unsaturated (poly) glycerin ester compound represented by the general formula (3) are used. 20 to 10 in a solvent capable of dissolving both raw materials such as toluene, hexane, chloroform, diisopropyl ether, and tetrahydrofuran in an amount of 0.5 to 10 times the total weight of the raw materials, or without solvent.
The reaction may be performed at 0 ° C. for 1 to 10 hours.

In this reaction, for the purpose of accelerating the reaction, a catalyst such as a transition metal such as platinum, rhodium, nickel and palladium, a compound of these transition metals, a complex of these transition metals and the like is used in a total amount of 10 raw materials. ^It is preferable to add ^-4 to 10 ^-6 moles. The reaction ratio of the starting organo (poly) siloxane to the terminal unsaturated (poly) glycerin ester compound (3) may be appropriately determined according to the degree of modification of the modified organo (poly) siloxane as the target compound, and particularly Although not limited, for example, when the number of Si—H bonds per molecule in the starting organo (poly) siloxane is J and all the J Si—H bonds are modified, a terminal unsaturated ester compound is used. (3) may be used in an amount of J to 2 J times the molar amount of the organo (poly) siloxane.

After the completion of the reaction, activated carbon or the like is added to remove the catalyst, the mixture is filtered, and the solvent and volatile matter are distilled off to obtain the (poly) glycerin ester-modified organo (poly) siloxane of the present invention. .

The thus-obtained (poly) glycerin ester-modified organo (poly) siloxane of the present invention has high detergency and good feel, and is therefore useful as a detergent component. The (poly) glycerin ester-modified organo (poly) of the present invention in the detergent composition of the present invention
The amount of siloxane blended will vary depending on the intended use,
It is preferably 1 to 60% by weight, particularly 2 to 30% by weight based on the total amount of the composition.

Further, the detergent composition of the present invention may contain other surfactants within the range not impairing the performance of the present invention. Such other surfactant may be either a nonionic surfactant or an ionic surfactant,
Examples of the nonionic surfactant include sorbitan monolaurate and other sorbitan fatty acid esters, glycerol monooleate and other glycerin fatty acid esters, sucrose monolaurate and other sucrose fatty acid esters, and polyoxyethylene lauryl ether and other polyoxyethylene. Examples include alkyl ethers, polyoxyethylene polyoxypropylene glycols, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene fatty acid esters, alkylalkanolamides, sugar ethers, sugar amides, and the like, and ionic surfactants such as potassium laurate. Fatty acid soaps, alkyl ether carboxylates such as sodium lauryl ether carboxylate, alkyl sulfates such as sodium lauryl sulfate, polyoxyethylene alkyl ether Acid salts, alkyl phosphates such as sodium monolauryl phosphate, sodium lauroyl-N-methyl taurine, N-acyl amino acid surfactants such as sodium N-lauroyl-L-glutamate, sulfosuccinic acid surfactants, Examples thereof include imidazoline-based surfactants commercially available as Milanol and softazoline, betaine-based surfactants such as betaine lauryl acetate, and amine oxides.

In the detergent composition of the present invention, if necessary, alcohols, liquid oils, fatty acids, water, cosmetics,
It may be mixed with medicinal agents, moisturizing ingredients, anti-inflammatory agents, bactericides, antiseptics, UV absorbers, antioxidants, thickeners, organic and inorganic powders, pigments, fragrances, etc. that are commonly used in pharmaceuticals. The dosage form can be any form such as liquid, gel, solid, and granules.

The detergent composition of the present invention can be produced by mixing the above components by a conventional method. The detergent composition of the present invention is used by applying it to the skin, hair, etc., massage it if necessary, and then rinsing it with water.

[0038]

The present invention will be further described with reference to examples and test examples, but the present invention is not limited to these examples. In the chemical formulas in the following examples, the degree of condensation of polyglycerin is an average value.

Embodiment 1

[0040]

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30 g of compound (3a) and 10 g of pentamethyldisiloxane (4a) were mixed and the temperature was raised to 70 ° C. Then, 200 μl of chloroplatinic acid [1% isopropyl alcohol (IPA) solution] was added, and the mixture was aged at 70 ° C. for 4 hours. After completion of the reaction, 100 ml of ethanol and 1 g of activated carbon were added, and the mixture was stirred at 60 ° C for 1 hour. The activated carbon was filtered, and ethanol was distilled off to give (poly) glycerin ester-modified organodisiloxane (2a) 36.
5 g (yield 98.3%) was obtained.

[0042]¹H-NMR 0.04ppm: Si (CH_Three)_Three, -0.02ppm: Si (CH_Three)_Two, 0.49ppm: Si-CH
_Two-CH_Two, 1.27ppm: Si-CH_Two-(CH _Two)₇, 1.61ppm: CH _Two-CH_Two-COO-,
2.33ppm: CH_TwoCH _Two-COO-, 3.2-4.1ppm: COO- (CH _TwoCH(OH) CH
_TwoO) ₆ H

Example 2

[0044]

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50 g of the compound (3b) and 15 g of heptamethyltrisiloxane (4b) were mixed and the temperature was raised to 70 ° C. Then, add 200μ of chloroplatinic acid (1% IPA solution)
l was added and the mixture was aged at 70 ° C. for 4 hours. After completion of the reaction, 100 ml of ethanol and 1 g of activated carbon were added, and the mixture was stirred at 60 ° C for 1 hour. Activated carbon was filtered and ethanol was distilled off to obtain 61.5 g (yield 99.2%) of polyglycerin ester-modified organotrisiloxane (2b).

[0046] ^{1 H-NMR 0.03ppm: Si (} CH 3) 3, -0.02ppm: Si-CH 3, 0.43ppm: Si-C H 2 -
CH ₂ , 1.21ppm: Si-CH _2- (C H ₂ ) ₇ , 1.59ppm: C H ₂ -CH ₂ -COO-, 2.
30ppm: CH ₂ C H ₂ -COO-, 3.2-4.1ppm: COO- (C H ₂ C H (O H ) C H ₂ O)
₁₀ - H

Example 3

[0048]

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50 g of the compound (3b) and 22 g of undecamethylpentasiloxane (4c) were mixed and the temperature was raised to 70 ° C. Then, add 20 ml of chloroplatinic acid (1% IPA solution).
0 μl was added and the mixture was aged at 70 ° C. for 4 hours. After the reaction,
100 ml of ethanol and 1 g of activated carbon were added, and the mixture was stirred at 60 ° C for 1 hour. Activated carbon was filtered and ethanol was distilled off to obtain 69.0 g (yield: 98.6%) of organopolysiloxane (2c) modified with foliglycerin ester.

[0050] ^{1 H-NMR -0.02ppm: Si-} CH 3, 0.41ppm: Si-C H 2 -CH 2, 1.21: ppm: Si-CH
_2- (C H ₂ ) ₇ , 1.60ppm: C H ₂ -CH ₂ -COO-, 2.31ppm: CH ₂ C H ₂ -COO
-, 3.2-4.1ppm: COO- (C H ₂ C H (O H ) C H ₂ O) ₁₀ - H

Example 4

[0052]

[Chemical 12]

30 g of compound (3c) and compound (4d)
44.8g was mixed and it heated up at 70 degreeC. After that, 250 μl of chloroplatinic acid (1% IPA solution) was added to 70 ° C.
Aged for 4 hours. After completion of the reaction, 100 ml of ethanol and 1 g of activated carbon were added, and the mixture was stirred at 60 ° C for 1 hour. By filtering the activated carbon and distilling off ethanol, a polyglycerin ester-modified organopolysiloxane (2d) is obtained.
73.9 g (yield 98.8%) was obtained.

[0054] ^{1 H-NMR 0.02ppm: Si-} CH 3, 0.78ppm: Si-C H 2 -CH 2, 2.35ppm: CH 2 -C H 2
-COO-, 3.2-4.1ppm: COO- (C H ₂ C H (O H ) C H ₂ O) ₆ - H

Example 5

[0056]

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30 g of compound (3d) and compound (4e)
37.2g was mixed and it heated up at 70 degreeC. After that, 200 μl of chloroplatinic acid (1% IPA solution) was added to 70 ° C.
Aged for 4 hours. After completion of the reaction, 100 ml of ethanol and 1 g of activated carbon were added, and the mixture was stirred at 60 ° C for 1 hour. By filtering the activated carbon and distilling off the ethanol, polyglycerin ester-modified organopolysiloxane (2e)
66.5 g (yield 99.0%) was obtained.

[0058] ^{1 H-NMR -0.03ppm: Si-} CH 3, 0.77ppm: Si-C H 2 -CH 2, 2.30ppm: CH 2 -C H
₂ -COO-, 3.2-4.1ppm: COO- (C H ₂ C H (O H ) C H ₂ O) ₁₀ - H

Example 6

[0060]

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40 g of compound (3b) and compound (4f)
52.4g was mixed and it heated up at 70 degreeC. After that, 200 μl of chloroplatinic acid (1% IPA solution) was added to 70 ° C.
Aged for 4 hours. After completion of the reaction, 100 ml of ethanol and 1 g of activated carbon were added, and the mixture was stirred at 60 ° C for 1 hour. By filtering the activated carbon and distilling off the ethanol, polyglycerin ester-modified organopolysiloxane (2f)
91.0 g (yield 98.5%) was obtained.

[0062] ^{1 H-NMR 0.01ppm: Si-} CH 3, 0.45ppm: Si-C H 2 -CH 2, 1.24: ppm: Si-CH 2
-(C H ₂ ) ₇ , 1.61ppm: C H ₂ -CH ₂ -COO-, 2.33ppm: CH ₂ -C H ₂ -COO
-, 3.2-4.1ppm: COO- (C H ₂ C H (O H ) C H ₂ O) ₁₀ - H

Example 7

[0064]

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40 g of compound (3b) and compound (4 g)
103.7g was mixed and it heated up at 70 degreeC. Then, add 200 μl of chloroplatinic acid (1% IPA solution),
Aged at ℃ for 4 hours. After the reaction, 100 ml of ethanol
And 1 g of activated carbon were added, and the mixture was stirred at 60 ° C. for 1 hour. By filtering the activated carbon and distilling off ethanol, the polyglycerin ester-modified organopolysiloxane (2
g) 141.5 g (yield 98.5%) was obtained.

[0066] ^{1 H-NMR -0.01ppm: Si-} CH 3, 0.41ppm: Si-C H 2 -CH 2, 1.20ppm: Si-CH 2
-(C H ₂ ) ₇ , 1.58ppm: C H ₂ -CH ₂ -COO-, 2.29ppm: CH ₂ -C H ₂ -COO
-, 3.2-4.1ppm: COO- (C H ₂ C H (O H ) C H ₂ O) ₁₀ - H

Example 8 A detergent composition having the composition shown in Tables 1 and 2 was prepared, and five panelists evaluated the detergency and feel of water resistant foundation, general foundation and general lipstick. (1) Test method A water resistant foundation, a general foundation or a general lipstick having the following composition was applied to several places on the inside of the forearm that had been washed with water so as to have a diameter of about 2 cm, and allowed to stand for 1 hour before washing.
It was thoroughly dried and used as a test site.

<Water-Resistant Foundation Composition> (wt%) Polymeric Silicone 5.0 Cyclic Silicone 27.0 Polyether Modified Silicone 3.0 Squalane 5.0 Dimethylpolysiloxane 10.9 Candelilla Wax 3.0 Perfume 0.1. 1 Silicone-coated sericite 15.0 Silicone-coated nylon powder 15.0 Silicone-coated titanium oxide 13.0 Silicone-coated iron oxide 3.0 Total 100.0

<General Foundation Composition> (wt%) Liquid paraffin 35.0 Squalane 15.0 Candelilla wax 3.0 Perfume 0.1 Ion-exchanged water 0.9 Cerisite 15.0 Nylon powder 15.0 Titanium oxide 13 0.0 Iron oxide 3.0 Total 100.0

<General Lipstick Composition> (wt%) Castor oil 50.0 Hexadecyl alcohol 25.0 Lanolin 5.0 Beeswax 4.0 Carnauba wax 7.0 Candelilla wax 2.0 Titanium oxide 2.0 Red No. 202 1 0.0 Red No. 204 3.0 Red No. 227 Al rake 1.0 Total 100.0

1 to 2 cleaning agent samples at each test site
The solution was dropped, and the finger pressure was immediately applied to about 100 g of finger pressure and rubbed twice per second for 10 seconds. Immediately thereafter, the finger was wetted with tap water and further rubbed twice per second for 5 seconds. Then, it was rinsed with running water and rubbed twice for 5 seconds while running.

(2) Evaluation Method <Detergency> The test sites were visually observed by the five panelists during and after the cleaning, and evaluated on the following four levels, and the average score was used for the evaluation. Score 4: Most makeup stains dissolve immediately and finally no residue can be observed. Score 3: It does not dissolve immediately, but gradually dissolves and finally no residue can be observed. Score 2: Slightly detergency is recognized, but finally, residual makeup stain is clearly recognized. Score 1: Almost no makeup stains are removed, as when washed with water. Judgment ◎: Average score 3.5 to 4.0 ○: Average score 2.5 to 3.4 Δ: Average score 1.5 to 2.4 ×: Average score 1.0 to 1.4

<Feeling> The feeling of the skin during and after washing in the above-mentioned washing power test was evaluated by the five panelists. Regarding the feeling during washing, the goodness of elongation was mainly evaluated. Regarding the feeling after washing, the moist feeling and the refreshing feeling are considered good, and the feeling of greasiness, stickiness, oiliness and sliminess are regarded as bad feelings. It was judged. Score 3: Good feeling or no difference in feeling from before washing. Score 2: A bad feeling is recognized. Score 1: Acceptably unacceptable feel. Judgment ◎: Average score 2.5 to 3.0 Δ: Average score 1.5 to 2.4 ×: Average score 1.0 to 1.4

(3) Results The results are shown in Tables 1 and 2.

[0075]

[Table 1]

[0076]

[Table 2]

[0077]

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Example 9 A makeup remover having the following formulation was prepared. (Wt%) Compound (2a) of Example 1 20.0 Polyoxyethylene (20) sorbitan monostearate 10.0 Sorbitol 10.0 Carrageenan 0.5 Perfume 0.1 Ion-exchanged water Balance meter 100.0 bottles When the foundation and lipstick were removed using the inventive make-up remover, they were removed satisfactorily and the feeling of use and foaming were also good.

Example 10 A hair make-up remover having the following formulation was prepared. (Wt%) Compound (2b) of Example 2 10.0 Polyoxyethylene (15) isocetyl ether 10.0 Glycerin 30.0 Carrageenan 0.5 Fragrance 0.1 Ion-exchanged water Balance meter 100.0 Hair make of the present invention When the hair was washed with a remover, hair make-up and sebum stains were satisfactorily removed and the usability was good.

Example 11 A face wash having the following formulation was prepared. (% By weight) Alkyl saccharide 10.0 Compound (2c) of Example 3 5.0 Polyoxyethylene (6) lauryl ether 5.0 Lauryl dimethylamine oxide 2.0 Propylene glycol 3.0 Ion-exchanged water Balance meter 100. 0 When the face was washed with the facial cleanser of the present invention, the feeling of use and foaming were also good.

Example 12 A makeup remover having the following formulation was prepared. (% By weight) Potassium monolauryl phosphate 15.0 Compound (2b) of Example 2 20.0 Polyoxyethylene (6) sorbitan monolaurate 3.0 Propylene glycol 5.0 Denatured ethanol 5.0 Ion-exchanged water balance 100.0 in total When the makeup remover of the present invention was used to remove the foundation and lipstick, the makeup and lipstick were removed satisfactorily, and the feeling of use and foaming were also good.

Example 13 A makeup remover having the following formulation was prepared. (Wt%) Compound (2c) of Example 3 20.0 Polyoxyethylene (20) sorbitan monostearate 10.0 Sorbitol 10.0 Carrageenan 0.5 Perfume 0.1 Ion-exchanged water Balance meter 100.0 bottles When the foundation and lipstick were removed using the inventive make-up remover, they were removed satisfactorily and the feeling of use and foaming were also good.

Example 14 A hair make-up remover having the following formulation was prepared. (Wt%) Compound (2a) of Example 1 10.0 Polyoxyethylene (15) isocetyl ether 10.0 Glycerin 30.0 Carrageenan 0.5 Fragrance 0.1 Ion-exchanged water Balance meter 100.0 Hair make of the present invention When the hair was washed with a remover, hair make-up and sebum stains were satisfactorily removed and the usability was good.

[0084]

The (poly) glycerin ester-modified organo (poly) siloxane of the present invention has excellent detergency and good feel. Therefore, the cleaning composition of the present invention containing this, lipstick that was difficult to remove makeup that has been difficult to remove conventionally, summer makeup, hair makeup and the like can be washed in a short time, and since it is excellent in foamability, it is whipped. It can be used, has good rinsability, and has a good feel during and after washing. Furthermore, it is also possible to use it in a condition where the skin is wet, which is not preferable to apply with the conventional gel type cleansing agent, for example, in a bathroom.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical display location C11D 1/82 C11D 1/82 // A61K 7/075 A61K 7/075 7/50 7/50

Claims (6)

[Claims] 1. The method of claim 1, wherein at least one silicon atom of the organo (poly) siloxane has the following general formula (1): [In formula, R < ¹ > shows a C2-C22 linear or branched alkylene group, m shows the number of 1-30. ] (Poly) glycerin ester modified organo (poly) siloxane characterized by being modified with a group represented by 2. In the general formula (1), R ¹ has 4 carbon atoms.
The (poly) glycerin ester-modified organo (poly) siloxane according to claim 1, which is a straight-chain alkylene group of -12 and m is a number of 3-20. 3. The following general formula (2): [In the formula, R ^{2 to} R ⁶ are the same or different and each represents an alkyl group or an alkoxyl group having 1 to 22 carbon atoms or a phenyl group, and at least one of X and n Y and Z is represented by the general formula (1 ) Is a group represented by
Represents an alkyl group, an alkoxyl group, or a phenyl group, and n represents a number of 0 to 1000. ] The (poly) glycerin ester-modified organo (poly) siloxane according to claim 1 or 2, which is a compound represented by the following formula. 4. In the general formula (2), a group other than the group represented by the general formula (1) among X, Y and Z, and R ^{2 to} R.
The (poly) glycerin ester-modified organo (poly) siloxane according to claim 3, wherein ⁶ is a methyl group. 5. An organo (poly) siloxane having at least one hydrogen atom bonded to a silicon atom has the following general formula (3): [In the formula, R ¹ ′ represents a single bond or a linear or branched alkylene group having 1 to 20 carbon atoms, and m represents a number of 1 to 30. ] The terminal unsaturated ester compound represented by these is made to react, The manufacturing method of the (poly) glycerin ester modified organo (poly) siloxane in any one of Claims 1-4. 6. A detergent composition containing the (poly) glycerin ester-modified organo (poly) siloxane according to any one of claims 1 to 4.