JPH07150190A - Detergent composition - Google Patents

Abstract

PURPOSE:To obtain a a detergent composition excellent in short-term detergency and foaming ability and also having good touch in washing by using a specified surfactant as the constituent. CONSTITUTION:This compositzon contarns a surfactant having structural units represented by formula I [wherein R<1> and R<3> are each 2-4C alkylene; R<2> is 2-22C alkylene; p is 0 or 1; q is 0 to 10; and X is a group of any one of formulas II to V (wherein Y<1> and Y<2> are each H, an alkali metal atom, ammonium, alkylamine or alkanolamine; m is 1 to 3; and n is 2 to 4)].

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a detergent composition, and more particularly, it shows a high detergency in a short time, especially for makeup stains such as lipsticks and foundations and hair cosmetics containing a hair protecting agent. The present invention relates to a detergent composition which exhibits excellent foaming power and has a good feel during and after washing.

[0002]

2. Description of the Related Art Conventionally, makeup stains such as lipsticks, foundations, eye shadows and mascaras contain a large amount of oil components such as solid fats, and ordinary face-washing foams mainly composed of soap are solubilized in these oil components. Since the ability to emulsify and emulsify is insufficient, it is impossible to remove such makeup stains. Therefore, cleansing creams, cleansing oils, gel-like cleansing agents mainly composed of an oily base have been used for cleaning makeup stains.

However, recent makeup cosmetics are
Good adhesion to the skin, high resistance to moisture and sebum, less likely to lose makeup, good makeup lasting, especially in summer makeup cosmetics with a large amount of sweat, such as cyclic silicone Many are based on oily solvents,
Furthermore, by mixing various binders such as a film-forming polymer and the like, there have been developed those which are less likely to lose their makeup.

On the other hand, also in hair cosmetics, various polymers are blended for the purpose of protecting the hair and imparting firmness, stiffness and the like to the hair.

[0005]

However, such a new problem that the stains caused by the cosmetics which do not easily lose their makeup or have excellent hair-protecting ability cannot be removed by the conventional cleansing detergents or shampoos. Has occurred.

Therefore, in addition to the conventional sebum stains, it is excellent in removing makeup stains, hair protectants and the like, and
It has been desired to develop a detergent composition having a high foaming property and a good feel during and after washing.

[0007]

In view of the above situation, the inventors of the present invention have conducted diligent research, and as a result, when a surfactant having a specific structural unit in the molecule was blended, makeup makeup such as summer makeup was damaged. It was found that an excellent cleaning effect can be obtained even against makeup stains that are difficult to do, and that it has a high foaming power, and that a detergent composition having a good feel during cleaning can be obtained.
The present invention has been completed.

That is, the present invention has the following general formula (1) in the molecule.

[0009]

[Chemical 3]

[In the formula, R ¹ and R ³ each have 2 carbon atoms.
To 4 alkylene groups, R ² represents a C 2-22 alkylene group, p represents a number of 0 or 1, and q represents 0 to 0.
10 is a number, and X is the following general formula (2), (3),
(4) or (5)

[0011]

[Chemical 4]

(Y ¹ and Y ² are each a hydrogen atom, an alkali metal atom, ammonium, an alkylamine or an alkanolamine, m is a number of 1 to 3, and n is 2
The present invention provides a detergent composition comprising a surfactant having a structural unit represented by the formula (1) to (4).

In the general formula (1) representing the structural unit contained in the surfactant used in the present invention, R ¹ and R ³ may be the same or different and each represents an alkylene group having 2 to 4 carbon atoms. R ² represents an alkylene group having ² to 22 carbon atoms, and an alkylene group having 6 to 15 carbon atoms is particularly preferable. p represents a number of 0 or 1, but 0 is particularly preferable. Moreover, q shows the number of 0-10, but 0-6 is especially preferable. Further, Y ^{1 in the} general formula (2), (3) or (4)
Alternatively, in the definition of Y ² , the alkali metal atom includes sodium, potassium, lithium atom and the like, the alkylamine includes trimethylamine, triethylamine and the like, and the alkanolamine includes triethanolamine, diethanolamine and the like. A hydrogen atom or an alkali metal atom is particularly preferable as Y ¹ or Y ² . Furthermore, in general formula (5), m shows the number of 1-3, n shows the number of 2-4.

The surfactant used in the present invention includes:
There is no particular limitation as long as it has a structural unit represented by the general formula (1) in the molecule, and examples thereof include those represented by the following general formula (6).

[0015]

[Chemical 5]

[Wherein at least one of R ⁴ , R ⁵ and R ⁶ is a group — (R ¹ O) _p —R ² — (OR ³ ) _q —X (R ¹ , R ² ,
R ³ , p, q and X have the same meaning as described above),
The remainder represents a methyl group, r represents a number from 0 to 4, and s represents 0.
~ Indicates the number of 5]

In the present invention, the general formula (6) is particularly preferable.
It is preferable that r = s = 0.

Among such surfactants, in order to produce those in which X is represented by the general formula (2), for example, a compound having a structural unit represented by the general formula (7) in the molecule ( Hereinafter, the compound (7) will be reacted with phosphorus oxyhalide, the phosphorus-halogen bond will then be hydrolyzed, and salt exchange will be carried out if necessary.

[0019]

[Chemical 6]

[Wherein R¹, R², R³, P, q, Y¹
And Y²Has the same meaning as above, X ¹Is a halogen atom
Indicates]

The reaction method of the compound (7) and phosphorus oxyhalide is not particularly limited, but, for example, a method of mixing each of them dissolved in a suitable solvent and reacting can be applied.

Examples of the solvent used for dissolving the compound (7) include tetrahydrofuran, methylene chloride, toluene and diethyl ether. The amount of the solvent used here is preferably 10 times or less, more preferably 3 times or less, with respect to the weight of the compound (7). Also,
Examples of the solvent used for dissolving the phosphorus oxyhalide include tetrahydrofuran, methylene chloride, toluene, ether and the like. The amount of solvent used here is preferably 20 times or less, more preferably 10 times or less, with respect to the weight of phosphorus oxyhalide.

The mixing ratio of the compound (7) and the phosphorus oxyhalide is not particularly limited, but 0.5 to 2, preferably 0, of the phosphorus oxyhalogenide is added to 1 equivalent of the hydroxyl group of the compound (7). It is preferable to mix so that it may become 0.9-1.5 equivalent.

The method of mixing the compound (7) with phosphorus oxyhalide is not particularly limited, but for example, a method of dropping the compound (7) into the phosphorus oxyhalide solution while applying stirring may be applied. You can

The dropping method in this case is not particularly limited, and, for example, a method of dropping the whole amount at once or appropriately dividing it, or a method of dropping little by little can be applied.
The temperature of the reaction system at the time of dropping is preferably -50 to 10 ° C, more preferably -30 to 0 ° C. After the completion of the reaction, it is preferable to perform an aging operation within the above temperature range for 1 to 5 hours, if necessary. In addition, in order to neutralize by-produced hydrochloric acid in the reaction system, a tertiary amine, for example, triethylamine, tributylamine, pyridine, N-methylmorpholine or the like can be made to coexist.

Next, in order to hydrolyze the phosphorus-halogen bond in the reaction product produced in the previous step, an alkaline solution is reacted by applying, for example, the same dropping method as above.

Examples of the alkaline solution used here include aqueous solutions of sodium hydroxide, potassium hydroxide, ammonia, alkylamines, alkanolamines and the like, with sodium hydroxide and potassium hydroxide being particularly preferred. Further, the concentration of the alkaline solution is not particularly limited and can be appropriately adjusted in consideration of the concentrations of the compound (7) and phosphorus oxyhalide. Further, the temperature of the reaction system is preferably set and maintained in the same temperature range as above, and the reaction time is preferably 1 to 15 hours.

After the reaction is completed in this way, the produced compound having the structural unit represented by the general formula (8) (hereinafter referred to as compound (8)) is separated from the reaction system. The compound (8) thus obtained may be further refined as necessary. This purification operation is not particularly limited, and for example, 1) adding water and a non-hydrophilic solvent such as butanol or toluene, and if necessary, a demulsifier such as ethanol or 2-propanol to the reaction mixture and stirring. Then, the mixture is allowed to stand to be separated into layers, and an aqueous layer containing excess phosphate and by-produced inorganic and organic salts is removed.
2) Remove the solvent from the reaction solution and wash the resulting residue with water to remove excess phosphate, or dissolve the residue in a solvent such as ethanol, propanol, butanol, or toluene. Thus, a method of removing excess precipitated phosphate by filtering; 3) When the produced compound (8) is insoluble in an organic solvent, a hydrophilic solvent such as ethanol or acetone is added to the separated aqueous layer. And a method of precipitating the target substance can be mentioned.

To prepare the surfactant represented by the general formula (1) in which X is represented by the general formula (3), the general formula (9) is added to the molecule in the molecule, for example, according to the following reaction formula.
A compound having a structural unit represented by (hereinafter referred to as compound (9)) is reacted with a halosulfonic acid, and then salt exchange may be carried out if necessary.

[0030]

[Chemical 7]

[Wherein R ¹ , R ² , R ³ , p, q, Y ¹
And X ¹ have the same meaning as above]

The reaction between the compound (9) and halosulfonic acid is not particularly limited, but, for example, a method in which each of them is dissolved in an appropriate solvent and mixed and reacted is applicable.

Examples of the solvent used for dissolving the compound (9) include tetrahydrofuran, methylene chloride, toluene and diethyl ether. The amount of the solvent used here is preferably 10 times or less, more preferably 3 times or less, with respect to the weight of the compound (9). Also,
Examples of the solvent used for dissolving the halosulfonic acid include tetrahydrofuran, methylene chloride, toluene, ether and the like. The amount of the solvent used here is preferably 20 times or less, more preferably 10 times or less, the weight of the halosulfonic acid.

The mixing ratio of the compound (9) and the halosulfonic acid is not particularly limited, but 0.5 to 2 equivalents of halosulfonic acid, preferably 0.9 to 1 is equivalent to 1 equivalent of the hydroxyl group of the compound (9). It is preferable to mix them so that the amount becomes 0.5 equivalent.

The method of mixing the compound (9) and the halosulfonic acid is not particularly limited, but, for example, a method of dropping the halosulfonic acid solution into the compound (9) solution while stirring may be applied.

The dropping method in this case is not particularly limited, and, for example, a method of dropping the whole amount collectively or appropriately dividedly, or a method of dropping little by little can be applied.
The temperature of the reaction system at the time of dropping is preferably -50 to 20 ° C, more preferably -30 to 10 ° C. After completion of the dropping, it is preferable to perform an aging operation for 1 to 5 hours within the above temperature range, if necessary. If the reaction system becomes acidic, the siloxane bond is likely to be cleaved, and alkali metal hydroxides, alkali metal carbonates, basic substances such as amines, preferably tertiary amines such as triethylamine, tributylamine,
It is preferable to coexist with pyridine, N-methylmorpholine and the like.

In the case of producing the compound (10) in which Y ¹ is ammonium, alkylamine or alkanolamine, the reaction may be terminated only by the above-mentioned production process, but Y ¹ is an alkali metal. In the case of producing, the alkaline solution is further dropped into the reaction product obtained in the previous step, for example, by applying the same dropping method as described above to react.

The alkaline solution used here is
Aqueous solution of sodium hydroxide, potassium hydroxide, ammonia, alkylamine, pyridine, alkanolamine, etc., sodium methylate, sodium ethylate,
Mention may be made of alcoholates such as potassium ethylate and potassium methylate, but especially sodium hydroxide,
An aqueous solution of potassium hydroxide, sodium methylate and potassium methylate are preferred. Further, the concentration of the alkaline solution is not particularly limited, and can be appropriately adjusted in consideration of the concentrations of the compound (9) and halosulfonic acid. Further, the temperature of the reaction system is preferably set and maintained in the same temperature range as above.

After the reaction is completed in this manner, the produced compound having the structural unit represented by the general formula (10) (hereinafter referred to as compound (10)) is separated from the reaction system. The compound (10) thus obtained may be further refined as necessary. The purification operation is not particularly limited, and for example, 1) a method in which the solvent is distilled off from the reaction solution, the solution is dissolved in a nonpolar solvent such as chloroform, and the inorganic salt produced as a by-product is filtered off; 2) The solvent is distilled from the reaction solution. Leave
Then insoluble in a solvent such as hexane and the precipitate is collected by filtration,
A method of removing unreacted and excess alcohol-modified organo (poly) siloxane can be mentioned.

In order to produce the surfactant represented by the general formula (1) in which X is represented by the general formula (4), it is represented by the general formula (11), for example, according to the following reaction formula. A compound (hereinafter, referred to as compound (11)) is reacted with a compound having a structural unit represented by general formula (12) in the molecule (hereinafter, referred to as compound (12)) to give the compound represented by general formula (13) in the molecule. A compound having a structural unit represented by the formula () (hereinafter referred to as compound (13)) is obtained, and after hydrolysis, salt exchange may be carried out if necessary.

[0041]

[Chemical 8]

[In the formula, R ⁷ represents a single bond, an alkylene group having 1 to 20 carbon atoms or a group —R ⁶ —OR ² — (R ⁶ represents a single bond or an alkylene group having 1 to 2 carbon atoms, and R ² Has the same meaning as above]

The reaction method of the compound (11) and the compound (12) is not particularly limited, but for example, a method of mixing the compound (11) and the compound (12) and reacting at 20 to 100 ° C. for 1 to 10 hours is applied. be able to. If necessary, a solvent capable of dissolving the compound (11) and the compound (12) may be added to carry out the reaction.

Examples of the solvent capable of dissolving the compound (11) and the compound (12) include toluene, hexane, chloroform, diisopropyl ether, tetrahydrofuran and the like. The amount of the solvent used is preferably 10 times or less the total weight of the raw materials. It is more preferably 3 times or less. In this reaction, for the purpose of accelerating the reaction, a catalyst such as a transition metal such as platinum, rhodium, nickel or palladium, a transition metal compound or a transition metal complex is used in a total amount of 10 ⁻⁴ to 10 ^−4.
It is preferable to add ^-6 times the molar amount.

Further, the mixing ratio of the compound (11) and the compound (12) may be appropriately determined according to the degree of modification of the target compound, and is not particularly limited. For example, the Si--H bond in the compound (12) can be used. When the number is J and all of the J Si—H bonds are modified, the compound (11) may be used in a J-fold mole or more, preferably in a J to 5 J-fold mole.

After completion of the reaction, to remove the catalyst, active carbon or the like is added and filtered, then the solvent is distilled off, and if necessary, purified by distillation, or the unreacted (excess) raw material is distilled off under reduced pressure. Gives compound (13).

The compound (13) is converted into the compound represented by the general formula (1
The reaction method for converting to a compound having the structural unit represented by 4) (hereinafter referred to as compound (14)) is not particularly limited, but for example, compound (13) and a base dissolved in a suitable solvent are mixed. A method of reacting in the presence of an appropriate amount of water can be applied. As a solvent used for dissolving the compound (13), tetrahydrofuran,
Examples thereof include methylene chloride, toluene, diethyl ether, methanol, hexane, ethanol and propanol. The amount of solvent used here is the compound (13)
The amount is preferably 10 times or less, and more preferably 3 times or less with respect to the weight. In addition, examples of the solvent used for dissolving the base include water, methanol, ethanol and the like. The amount of solvent used here is preferably 20 times or less, more preferably 10 times or less, based on the weight of the base.

The mixing ratio of the compound (13) and the base is not particularly limited, but is 0.5 to 2 equivalents, preferably 1 to 1.2 equivalents of the base with respect to 1 equivalent of the structural unit (13) of the compound (13). It is preferable to mix so that.

The method of mixing the compound (13) and the base is not particularly limited, but, for example, a method of dropping the base solution into the compound (13) solution while stirring may be applied as necessary. The dropping method in this case is not particularly limited, and, for example, a method of dropping the whole amount collectively or appropriately and dropping or a method of dropping little by little can be applied. The temperature of the reaction system at the time of dropping is preferably 0 to 100 ° C,
10-40 degreeC is more preferable. After completion of the dropping, it is preferable to perform an aging operation for 1 to 10 hours within the above temperature range, if necessary.

Examples of the base used here include sodium hydroxide, potassium hydroxide, sodium methylate, potassium methylate, sodium ethylate, potassium ethylate and the like, but especially sodium hydroxide and water. Potassium oxide is preferred. Further, the concentration of the base is not particularly limited and can be appropriately adjusted in consideration of the concentration of the compound (13).

In the case of producing the compound (14) in which Y ¹ is an alkali metal, the reaction may be terminated only by distilling off the solvent (solvent) after carrying out the above production steps. In the case where Y ¹ is ammonium, alkylamine or alkanolamine, it may be reacted as follows. That is, after adding 1 to 3 equivalents, preferably 1 to 2 equivalents of an acidic aqueous solution to the base added to the reaction solution, and then adding a solvent such as hexane, ether, methylene chloride, and separating the organic layer. If necessary, it may be washed with ion-exchanged water, necessary amounts of ammonium, alkylamine and alkanolamine may be added to the obtained organic layer, and the solvent may be distilled off. Examples of the acidic aqueous solution used here include aqueous solutions of hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, perchloric acid, and the like, but aqueous solutions of hydrochloric acid, sulfuric acid, and the like are particularly preferable.

Further, among the surfactants represented by the general formula (1), those in which X is represented by the general formula (5) can be produced, for example, by the general formula (15) according to the following reaction formula. The compound (hereinafter referred to as the compound (15)) may be reacted with the compound (12).

[0053]

[Chemical 9]

[Wherein R ¹ , R ² , R ³ , R ⁷ , p,
q, n and m have the same meanings as above]

The reaction method of the compound (15) and the compound (12) is not particularly limited, but for example, a method of mixing the compound (15) and the compound (12) and reacting at 20 to 100 ° C. for 1 to 10 hours is applied. can do. Further, if necessary, a solvent capable of dissolving the compound (15) and the compound (12) can be added to carry out the reaction.

Examples of the solvent capable of dissolving the compound (15) and the compound (12) include toluene, chloroform, diisopropyl ether and tetrahydrofuran.
The amount of the solvent used is preferably 10 times or less the total weight of the raw materials, and more preferably 3 times or less. In this reaction, for the purpose of promoting the reaction, a catalyst such as a transition metal such as platinum, rhodium, nickel or palladium, a transition metal compound or a transition metal complex is added in a molar amount of 10 ^-4 to 10 ^-6 times the total amount of the raw materials. It is preferable.

Further, the mixing ratio of the compound (15) and the compound (12) may be appropriately determined according to the degree of modification of the target compound and is not particularly limited. For example, the Si--H bond in the compound (12) can be When the number is J and all of the J Si—H bonds are modified, the compound (15) may be used in a J-fold molar amount or more, preferably in a J to 5 J-fold molar amount.

After completion of the reaction, activated carbon or the like is added to remove the catalyst, the mixture is filtered, and then the solvent is distilled off to obtain a compound having a structural unit represented by the general formula (16) (hereinafter referred to as compound (16)). Referred to as) can be obtained. The compound (16) thus obtained can be further refined, if necessary. The purification method is not particularly limited, and examples thereof include a method in which the solvent is distilled off from the reaction solution, the solution is dissolved in a nonpolar solvent such as hexane, and the unreacted material is filtered off.

The surfactants thus obtained all have a high foaming property and can improve the compatibility with oil components such as silicone, and are therefore useful as a detergent component.

Further, these surfactants are preferably used as a detergent composition dissolved or dispersed in an aqueous medium, and the compounding amount thereof varies depending on the purpose of use, but is 1 to 60% by weight in the total amount of the composition. It is particularly preferable that the amount is 2 to 30% by weight.

Further, the detergent composition of the present invention may contain other surfactant 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 activator include sorbitan fatty acid esters such as sorbitan monolaurate, glycerin fatty acid esters such as glycerol monooleate, sucrose fatty acid esters such as sucrose monolaurate, and polyoxyethylene alkyls such as polyoxyethylene lauryl ether. Ether, polyoxyethylene polyoxypropylene glycol, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene fatty acid ester, alkyl alkanolamide, sugar ether, sugar amide and the like, and the ionic surfactant includes potassium laurate and the like. Fatty acid soap, alkyl ether carboxylate such as sodium lauryl ether carboxylate, alkyl sulfate such as sodium lauryl sulfate, polyoxyethylene alkyl ether sulfate , Alkyl phosphates such as sodium monolauryl phosphate, N-acyl amino acid activators such as sodium lauroyl-N-methyl taurine, sodium N-lauroyl-L-glutamate, sulfosuccinic acid activators, milanol, and softofazoline Examples thereof include imidazoline activators, betaine lauryl acetate betaine and the like, amine oxides and the like. Further, in the detergent composition of the present invention, alcohols, liquid oils, fatty acids, water, as well as medicinal agents, moisturizing ingredients, anti-inflammatory agents, bactericides and antiseptics usually used in cosmetics, pharmaceuticals, etc. Agents, UV absorbers, antioxidants, thickeners, organic and inorganic powders, pigments, fragrances, etc. can be added, and the dosage form can be any form such as liquid, gel, solid, granules, etc. be able to.

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.

[0063]

EFFECTS OF THE INVENTION With the detergent composition of the present invention, it is possible to wash makeup such as lipstick, summer makeup and hair makeup which have been difficult to remove in the past, in a short time, and to have excellent foaming property. It can be used by foaming, 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.

[0064]

The present invention will be further described below with reference to examples, but the present invention is not limited thereto.

Synthesis Example 1

[0066]

[Chemical 10]

15 g of an organosiloxane (a) modified with an alcohol at one end synthesized by a known method, pyridine 7.
5 g and methylene chloride 10 g were mixed and cooled to 0 ° C. A mixed solution of 5.5 g of chlorosulfonic acid (b) and 10 g of methylene chloride was added dropwise to this solution over 20 minutes while maintaining the temperature at 10 ° C or lower. After aging for 4 hours at 10 ° C or lower,
Sodium methylate (28% methanol solution) 18.
2 g was added dropwise in 15 minutes while keeping the temperature below 10 ° C. Then, the temperature was gradually raised and the mixture was stirred at room temperature for 2 hours. After completion of stirring, the solvent was distilled off under reduced pressure. Add chloroform to the residue,
The insoluble matter was filtered off, the solvent was distilled off, hexane was further added, and the resulting solid was collected by filtration to obtain 17 g of a sulfonic acid ester-modified organosiloxane (c).

[0068] _{^{1 H-NMR (D 2 O}} ) δ (ppm): -0.02; -CH 2 -Si-C H 3 0; Si- (C H 3) 3 0.46; -C H 2 - _{Si-CH 3 1.24; -CH 2} - 1.60; -C H 2 -CH 2 -OSO 3 Na 3.94; -CH 2 -C H 2 -OSO 3 Na

Synthesis Example 2

[0070]

[Chemical 11]

A solution prepared by dissolving 13.2 g of phosphorus (e) oxychloride in 20 g of tetrahydrofuran was cooled to -30 ° C. Next, a known method (Japanese Patent Laid-Open No. 62-62-
A solution prepared by dissolving 28.2 g of one-terminal-alcohol-modified dimethylsiloxane (d) synthesized in 195389) and 8.7 g of triethylamine in 30 g of tetrahydrofuran was added dropwise over 20 minutes. Then, it was aged for 4 hours while keeping the reaction temperature at -20 ° C or lower. Then, a solution prepared by dissolving 17.5 g of sodium hydroxide in 30 g of ion-exchanged water was added dropwise to the reaction solution in 20 minutes. Stirring was continued at 0 ° C. for 12 hours to complete the reaction. Then, 70 g of ion-exchanged water and a mixed solvent of ether and ethanol were added to the reaction solution,
The reaction product was extracted. Thereafter, the organic layer was washed with ion-exchanged water, the aqueous layer was removed, and then the solvent was distilled off under reduced pressure to obtain 32 g of phosphoric acid ester-modified dimethylsiloxane (f).

³¹ P-NMR (D ₂ O): 8.0 ppm ¹ H-NMR (D ₂ O) δ (ppm): 0.3; —O—Si— (CH ₃ ) ₂ —CH ₂ — 0 _{.6; (C H 3) 3} Si-O 0.5; Si-C H 2 1.2; -CH 2 - (C H 2) 8 -CH 2 -CH 2 -O-P 1.6; - _{C H 2 -CH 2 -O-P} 3.8; -C H 2 -O-P IR: Si-O-Si; 1050cm -1 Si-C; 1245cm -1, 840cm -1

Synthesis Example 3

[0074]

[Chemical 12]

Undecylenic acid methyl ester (g) 30
g, 23 g of pentamethyldisiloxane (h) and 20 g of toluene were mixed. Add platinum catalyst to this solution,
It was aged at ℃ for 3 hours. After the reaction was completed, 1 g of activated carbon was added, and the mixture was stirred at 50 ° C. for 1 hour. After the activated carbon was filtered off, toluene was distilled off under reduced pressure. The obtained residue was distilled under reduced pressure to obtain 50 g of ester-modified organosiloxane (i). 20 g of the ester-modified organosiloxane (i) obtained by the above method was mixed with 50 g of ion-exchanged water and 50 g of ethyl alcohol. Sodium hydroxide (j) was added to this solution.
2.4 g was added, and the mixture was stirred at room temperature for 10 hours. The solvent was distilled off under reduced pressure and the carboxylic acid-modified organosiloxane (k) 19.
8 g was obtained.

¹ H-NMR (D ₂ O) δ (ppm): 0; —CH ₂ —Si—C H ₃ 0.02; Si— (C H ₃ ) ₃ 0.48; —C H ₂ —Si _{-CH 3 1.27; -CH 2 - 1.54} ; -C H 2 -CH 2 -COONa 2.10; -CH 2 -C H 2 -COONa

Synthesis Example 4

[0078]

[Chemical 13]

A platinum catalyst was added to a solution prepared by mixing 22 g of compound (l), 10 g of pentamethyldisiloxane (m) and 5 g of toluene, and aged at 70 ° C. for 4 hours. After the reaction was completed, 50 g of toluene and 1 g of activated carbon were added, and the mixture was stirred at 50 ° C. for 1 hour. After filtering off the activated carbon, the solvent was distilled off under reduced pressure to obtain 30.6 g of betaine-modified organosiloxane (n).

[0080] _{^{1 H-NMR (CDCl 3 +}} CD 3 OD) δ (ppm): -0.05; -CH 2 -Si-C H 3 -0.02; O-Si-CH 3 0.41; -C _{H 2 -Si-CH 3 1.18;} -CH 2 - 1.52; CO-CH 2 -C H 2 1.83; CO-NH-CH 2 - 2.10; CO-C H 2 -CH 2 _{3.13; N-CH 3 3.19;} -CH 2 -N- 3.46; -CH 2 -C H 2 -CH 2 -N 3.60; N-CH 2 -COO -

Example 1 A cleaning composition having the composition shown in Table 2 was prepared according to a conventional method,
The detergency and feel to the water resistant foundation and the foaming power were evaluated. The results are shown in Table 2.

(1) Test method A water resistant foundation having the following composition was applied to the inside of the forearm that had been washed with water.

[0083]

[Table 1] [Foundation composition] (wt%) Polymeric silicone 5.0 Cyclic silicone 27.0 Polyether-modified silicone 3.0 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 Iron oxide 3.0 Total 100.0

The application was performed so that the diameter was about 2 cm at several points on the forearm, left for 1 hour before washing, and sufficiently dried to make each test site. The cleaning agent sample was dropped on each test site in one or two drops, and immediately, with a finger, a finger pressure of 100 g was applied.
It was squeezed to a degree 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 site was visually observed by the panelists during and after the cleaning, and evaluated on the following four scales. ⊚: Most of the foundation was immediately dissolved, and finally no residue was observed. ◯: It does not dissolve immediately, but gradually dissolves and finally no residue can be observed. Δ: Some detergency is recognized, but finally residual foundation is clearly recognized. X: Almost no foundation is removed as in the case of washing with water.

[Feeling Feel] The feeling of the skin during and after washing in the above-mentioned detergency 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 were regarded as good feelings, and the feeling of greasiness, stickiness, oiliness, and sliminess were regarded as bad feelings, and the sensory test evaluated the following three grades. ◯: A good feeling is recognized, or no difference in the feeling before and after washing is recognized. Δ: A bad feeling is recognized. X: An unacceptable bad touch is recognized.

[Foaming Power] 2% aqueous solution of the detergent composition 10
0 ml was inverted and stirred for 30 seconds, and after 10 seconds, the amount of foam was measured. ◯: The amount of foam exceeds 150 ml. Δ: The amount of foam is 50 ml or more and 150 ml or less. X: The amount of foam is less than 50 ml.

[0088]

[Table 2]

Example 2 A cleansing cream having the following composition was prepared according to a conventional method. This was excellent in detergency and feel to the water resistant foundation.

[0090]

[Table 3] (Composition) (% by weight) Sulfonate-modified organosiloxane (Synthesis example 1) 50.0 Sodium stearate 5.0 Polyethylene glycol (average molecular weight 6000) 10.0 Sorbitol 5.0 Glycerin 5.0 Carboxy Vinyl Polymer 0.5 Fragrance Trace Methyl Paraben Trace Trace Propyl Paraben Trace Trace Purified Water Balance

Example 3 A shampoo having the following composition was prepared by a conventional method. It was excellent in detergency, foaming power and feel.

[0092]

[Table 4] (Composition) (wt%) Sulfonate-modified organosiloxane (Synthesis example 1) 7.0 Sodium cocoyl isethionate 1.0 Sodium cocoyl glutamate 1.0 Cocoamidopropyl betaine 1.0 Ethanol 4.0 Hydroxyethyl cellulose 0.2 Fragrance Trace amount Colorant Trace amount Purified water Balance

Example 4 A cleansing cream having the following composition was prepared by a conventional method. This was excellent in detergency and feel to the water resistant foundation.

[0094]

[Table 5] (Composition) (wt%) Phosphate ester-modified dimethyl siloxane (Synthesis example 2) 50.0 Sodium stearate 5.0 Polyethylene glycol (average molecular weight 6000) 10.0 Sorbitol 5.0 Glycerin 5.0 Vaseline 18.0 Liquid paraffin 5.0 Carboxyvinyl polymer 0.5 Perfume Trace methyl paraben Trace propylparaben Trace purified water Balance

Example 5 A shampoo having the following composition was prepared by a conventional method. It was excellent in detergency, foaming power and feel.

[0096]

[Table 6] (Composition) (wt%) Phosphate ester-modified dimethyl siloxane (Synthesis example 2) 7.0 Alkylsulfate triethanolamine salt (AS-TEA) 5.0 Coconut fatty acid monoethanolamide 2.0 Cocoyl isethione Sodium acid 1.0 Sodium cocoyl glutamate 1.0 Cocoamidopropyl betaine 1.0 Ethanol 4.0 Hydroxyethyl cellulose 0.2 Perfume Trace colorant Trace amount Purified water Balance

Example 6 A cleansing cream having the following composition was prepared by a conventional method. This was excellent in detergency and feel to the water resistant foundation.

[0098]

[Table 7] (Composition) (wt%) Carboxylic acid-modified organosiloxane (Synthesis example 3) 50.0 Sodium stearate 5.0 Polyethylene glycol (average molecular weight 6000) 10.0 Sorbitol 5.0 Glycerin 5.0 Liquid paraffin 3.0 Cetyl alcohol 1.2 Carboxyvinyl polymer 0.5 Perfume Trace methyl paraben Trace propyl paraben Trace purified water Balance

Example 7 A shampoo having the following composition was prepared by a conventional method. It was excellent in detergency, foaming power and feel.

[0100]

[Table 8] (Composition) (wt%) Carboxylic acid-modified organosiloxane (Synthesis example 3) 17.0 Sodium alkyl ether sulfate (AES-Na) 10.0 Lauric acid diethanolamide 4.0 Sodium cocoylisethionate 1. 0 Ethanol 4.0 Hydroxyethyl cellulose 0.2 Fragrance Trace amount Colorant Trace amount Purified water Balance

Example 8 A cleansing cream having the following composition was prepared according to a conventional method. This was excellent in detergency and feel to the water resistant foundation.

[0102]

Table 9 (Composition) (wt%) Betaine modified organosiloxane (Synthesis example 4) 50.0 Sodium stearate 5.0 Polyethylene glycol (average molecular weight 6000) 10.0 Sorbitol 5.0 Glycerin 5.0 Carboxyvinyl polymer 0.5 Fragrance Trace Methyl Paraben Trace Trace Propyl Paraben Trace Purified Water Balance

Example 9 A shampoo having the following composition was prepared by a conventional method. It was excellent in detergency, foaming power and feel.

[0104]

[Table 10] (Composition) (wt%) Betaine modified organosiloxane (Synthesis example 4) 7.0 Polyoxyethylene sorbitan fatty acid ester 5.0 Sodium cocoyl isethionate 1.0 Sodium cocoyl glutamate 1.0 Cocoamidopropyl betaine 1.0 Ethanol 4.0 Hydroxyethyl cellulose 0.2 Fragrance Trace amount Colorant Trace amount Purified water Balance

Claims (1)

[Claims] 1. A compound represented by the following general formula (1): [In the formula, R ¹ and R ³ each represent an alkylene group having 2 to 4 carbon atoms, R ² represents an alkylene group having 2 to 22 carbon atoms, p represents a number of 0 or 1, and q represents 0 to 0. 10 is a number, and X is the following general formula (2), (3), (4) or (5): (Y ¹ and Y ² each represent a hydrogen atom, an alkali metal atom, ammonium, an alkylamine or an alkanolamine, m represents a number of 1 to 3, and n represents a number of 2 to 4). [Shown]] A detergent composition comprising a surfactant having a structural unit represented by