JP3389311B2 - Glyceryl ether-modified organo (poly) siloxane, process for producing the same, and cosmetics containing the same - Google Patents

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a glyceryl ether-modified organo (poly) siloxane useful as a base for cosmetics, an emulsifier, a lubricant, a liquid crystal forming agent, etc., a process for producing the same, and a cosmetic containing the same. .

[0002]

PRIOR ART AND PROBLEMS TO BE SOLVED BY THE INVENTION Organo (poly) siloxane (silicone oil) is used as a finishing agent for hair and as a component of various cosmetics because it has a low stickiness and is highly safe. Has been done. However, organo (poly) siloxane is inferior in performance such as emulsion stability, solubility in water, and lubricity, so that further improvement in performance is required. In order to satisfy such requirements, modified organo (poly) siloxanes having various functional groups introduced therein, such as amino modified, epoxy modified, carboxylic acid modified, mercapto modified, alcohol modified, polyether modified, fluoroalkyl modified, alkyl. Modified and alkoxy modified organo (poly) siloxanes have been studied and developed.

However, the above-mentioned conventional modified organo (poly) siloxane has not been sufficiently satisfactory as a blending component for cosmetics. For example, polyether-modified organo (poly) siloxane has a problem that it is not suitable for practical use because it has a cloud point phenomenon, which is a characteristic of nonionic surfactants having a polyether bond, and has poor temperature stability in an emulsion system. It was Therefore, it has been desired to develop an organo (poly) siloxane useful as a base for cosmetics, an emulsifier, a lubricant, a liquid crystal forming agent and the like.

[0004]

Under the circumstances, the inventors of the present invention have conducted diligent research, and as a result, the general formula (1)

[0005]

[Chemical 6]

(R ¹ is a straight-chain or branched alkyl group having 6 to 20 carbon atoms.
Rxylene group, X, Y, Z are all hydroxymethyl
Group, X is a hydroxymethyl group, one of Y and Z is a hydroxyl group,
The other is a hydrogen atom. ) A glyceryl ether-modified organo (poly) siloxane containing a group represented by ) forms a liquid crystal in a water dispersion system, exhibits extremely excellent lubricity, and has compatibility with almost all solvents. Shows,
And it is found that when it is mixed with water, it has properties such as being almost uniformly and easily dispersed, and that it exhibits extremely excellent performance as a cosmetic base, an emulsifier, a lubricant, and a liquid crystal forming agent, which has never been achieved. The present invention has been completed.

That is, the present invention relates to general formulas (7A) to (1
The present invention provides a glyceryl ether-modified organo (poly) siloxane represented by any one of 1A), a method for producing the same, and a cosmetic containing the same.

[0008]

[Chemical 7]

[In the formula, R ^{3 to} R ¹³ each have 1 to 2 carbon atoms.
2 represents an alkyl group, an alkoxy group or a phenyl group,
a is a number from 1 to 1000, b, d, and e are numbers from 0 to 1000, respectively.
Where A is equation (3)

[0010]

[Chemical 8]

(R ¹ is a straight-chain or branched alkyl group having 6 to 20 carbon atoms.
Rxylene group, X, Y, Z are all hydroxymethyl
Group, X is a hydroxymethyl group, one of Y and Z is a hydroxyl group,
The other is a hydrogen atom). ] Below,
BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail, but the "organo (poly) siloxane" in the present invention is meant to include a high molecular weight organopolysiloxane to a low molecular weight organopolysiloxane.

In the formula (3) , R ¹ represents a linear or branched alkylene group having 6 to 20 carbon atoms, specifically, hex
Len , heptylene, octylene, nonylene, decylene,
Undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, 2
- ethyl hexylene, 2- Buchirudeshiren, 2- Echirudodeshiren, 2- Buchirudodeshiren, 2-ethyl tetra decylene, 2-hexyl decylene, 2-butyl tetra decylene, 2-ethylhexanol decylene, 2-hexyl dodecylene , 2-butylhexadecylene, 2-ethyloctadecylene, 2-hexyltetradecylene, 2-octyldodecylene, 2- heptylundecylene, 2- (1,
3,3-trimethylbutyl) octylene, 5,7,7-
Trimethyl-2- (1,3,3-trimethylbutyl) octylene and the following formula (6)

[0013]

[Chemical 9]

(Wherein p is an integer of 5 to 11, q is an integer of 5 to 11, p + q is 12 to 18, and p = 8 and q =
And an alkylene group such as methyl-branched isostearylene having a distribution having 8 as the apex).

The groups represented by X, Y and Z are silicones.
In terms of emulsifying power, etc. of the oil, X, Y, or Z are all hydroxymethyl group, X is a hydroxymethyl group, Y, one hydroxyl group of Z, the other is hydrogen atom.

Any of the general formulas (7A) to (11A)
The glyceryl ether-modified organo (poly) siloxane represented by these is not particularly limited, such as a structure in which siloxane units are linearly linked, a structure in which they are networked, a mixed type structure thereof, and the like. However, the glyceryl ether-modified organo (poly) siloxane represented by the general formula (2) is particularly preferable in terms of availability as an industrial product and easy handling.

[0017]

[Chemical 10]

[In the formula, R ² is an alkyl group having 1 to 22 carbon atoms,
Represented by an alkoxyl group, a phenyl group or the above formula (3)
And n is a number from 0 to 1000, but 2n + 6 R ²
May be the same or different, and at least one is a group represented by the formula (3). ] In the general formula (2),
Among the alkyl group having 1 to 22 carbon atoms, the alkoxyl group and the phenyl group represented by R ² , an alkyl group or alkoxyl group having 1 to 6 carbon atoms is preferable, and a methyl group is particularly preferable.
Further, n in the formula (2) is a number of 0 to 1000, and within that range, n is preferably 0 to 300, and particularly preferably 0 to 50.

General formulas (7A) to (11A) of the present invention
Glyceryl ether-modified organo (poly) siloxane represented by a gap (hereinafter abbreviated as glyceryl ether-modified organo (poly) siloxane (7A) to (11A) )
Is manufactured as follows. That is, general formula (7)-
It can be produced by reacting the organo (poly) siloxane represented by (11) with the compound represented by the general formula (5).

[0020]

[Chemical 11]

[ Wherein R ^{3 to} R ¹³ , a, b, d and e are the same as those defined above]
Have the same meaning. ]

[0022]

[Chemical 12]

[0023] [In the formula, R ^{1 'represents} a linear or branched alkylene group having 4 to 18 carbon atoms, m represents a 1, X, Y, Z are as defined above. Specific examples of the organo (poly) siloxane represented by the general formulas (7) to (11) include:
For example, 1,3,5,7,9-pentamethylcyclopentasiloxane, 1,3,5,7-tetramethylcyclotetrasiloxane, 1,1,1,3,5,7,7,7-octamethyl Tetrasiloxane, tris (trimethylsiloxy) silane, 1,1,3,3,5,5-hexamethyltrisiloxane, 1,1,1,3,5,5,5-heptamethyltrisiloxane, 1,1, 3,3,5,5,5-
Heptamethyltrisiloxane, pentamethyldisiloxane, 1,1,3,3-tetramethyldisiloxane, 1,
3-diphenyl-1,3-dimethyldisiloxane, 1,
1,1,3,3,5,5-heptamethyltrisiloxane, methyltris (dimethylsiloxy) silane, 1,
1,3,3,5,5,7,7-octamethyltetrasiloxane, 1,1,1,3,5,7,7,7-octamethyltetrasiloxane and the like can be mentioned.

In the present invention, such an organo (poly) is used.
Although siloxane manufactured by a known method can be used, a commercially available product can be used as it is, and specific examples thereof include TSF484, TSF483,
XF40-A2606, XF40-A1629, XF4
0-A5149, XF40-A2484, XF40-A
2428 (above, manufactured by Toshiba Silicone Co., Ltd.) and the like.

The compound represented by the above general formula (5) may be produced by any method, for example, it can be produced according to the following formula.

[0026]

[Chemical 13]

[In the formula, R ^{1 ′} , m, X, Y and Z have the same meanings as described above. That is, the compound represented by the general formula (12) and a compound represented by the general formula (13) in an amount of 1 to 10 moles are used without solvent or in a solvent such as dimethyl sulfoxide or dimethylacetamide, if necessary, sodium hydroxide, The reaction may be carried out at a temperature of 50 to 200 ° C. for 1 to 10 hours in the presence of a catalyst such as potassium hydroxide.

In this reaction, when the compound represented by the general formula (13) is a polyhydric alcohol, one molecule of the compound represented by the general formula (12) is added to one molecule of this polyhydric alcohol to give 1 mol. Adduct (compound represented by general formula (5))
In addition to the above, a polymolar adduct in which two or more molecules of the compound represented by the general formula (12) are added to one molecule of this polyhydric alcohol is obtained, and a mixture thereof is obtained. Usually, there is no problem in using a mixture of these 1-mole adducts or poly-mole adducts as they are, but if necessary, it can be purified using a known purification method such as a silica gel column or solvent extraction.

In order to carry out the production method of the present invention, the organo (poly) siloxane represented by the general formulas (7) to (11) and the compound represented by the general formula (5) are required, if necessary. The reaction may be carried out at 20 to 100 ° C. for 1 to 10 hours in a solvent capable of dissolving both raw materials such as toluene, hexane, chloroform and tetrahydrofuran in an amount of 0.5 to 10 times the total weight of the raw materials.

In this reaction, for the purpose of accelerating the reaction, a transition metal such as platinum, rhodium, nickel or palladium, a compound of these transition metals, or a catalyst such as a transition metal complex thereof is used in a total amount of 10 ^{− It} is preferable to add ⁴ to 10 ^-6 times by mole. Further, the reaction ratio of the organo (poly) siloxane as the raw material to the compound represented by the general formula (5) depends on the glyceryl ether-modified organo (poly) siloxane (7A) to (11A) as the target compound. It may be appropriately determined according to the degree of modification and is not particularly limited. For example, the number of Si—H bonds in the starting organo (poly) siloxane is 5, and
If you want to denature all five of the Si-H bonds,
The compound represented by the general formula (5) may be used in a molar amount 5 times or more, preferably 5 to 25 times, that 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 is distilled off to give the glyceryl ether-modified organo (poly) siloxane of the present invention.
(7A) to (11A) are obtained.

The cosmetic of the present invention contains glyceryl ether-modified organo (poly) siloxane (7A) to (11A) as an essential component, and the glyceryl ether-modified organo (poly) siloxane (7A) in the cosmetic of the present invention. ~
The compounding amount of (11A) is preferably 0.1 to 20% by weight, and 0.5
Especially preferred is -10% by weight.

The cosmetic of the present invention comprises the glyceryl ether-modified organo (poly) siloxane (7A) to (11).
In addition to A) , components used in ordinary cosmetics, such as ethylene glycol, diethylene glycol, triethylene glycol, higher polyethylene glycols, propylene glycol, dipropylene glycol, higher polypropylene glycols, 1,3-butylene Glycerol, butylene glycols such as 1,4-butylene glycol, glycerin, diglycerin, and higher polyglycerins, sugar alcohols such as sorbitol, mannitol, xylitol, maltitol, ethylene oxide of glycerins (hereinafter abbreviated as EO). ), Propylene oxide (hereinafter abbreviated as PO) adduct, sugar alcohols EO and PO adducts, monosaccharides such as galactose, glucose and fructose and their EO and PO adducts, maltose and lactose. Polysaccharides and polyhydric alcohols such as EO and PO adducts; hydrocarbons such as liquid paraffin, squalane, vaseline and solid paraffin, olive oil, jojoba oil, evening primrose oil, coconut oil, natural oils such as beef tallow, isopropyl myristate , Ester oils such as cetyl isooctanoate and neopentyl glycol dicaprate, silicone oils such as methyl silicone and methyl phenyl silicone, oily components such as higher fatty acids such as isostearic acid and oleic acid; polyoxyethylene (hereinafter POE and Abbreviation) alkyl ether, POE branched alkyl ether,
Nonionic surfactants such as POE sorbitan ester, POE glycerin fatty acid ester, POE hydrogenated castor oil, sorbitan ester, glycerin fatty acid ester, polyglycerin fatty acid ester, phosphoric acid type, sulfonic acid type, sulfuric acid type, carboxylic acid type, etc. Anionic surfactant, other amphoteric surfactant, cationic surfactant, etc .;
Antibiotics such as vitamins, triclosan, trichlorocarban, etc., anti-inflammatory agents such as dipotassium glycyrrhizinate, tocopherol acetate, antidandruff agents such as zinc pyrithione, octopirox, activators, UV absorbers; methylparaben, butylparaben, etc. Antiseptics, foaming agents such as alkylamine oxides, fatty acid alkanolamides, inorganic salts, viscosity modifiers such as polyethylene glycol stearate ethanol, pearling agents, fragrances, pigments, antioxidants; montmorillonite, saponite, hecklite, bee gum , Water-swelling clay minerals such as Kunivia and smecton; carrageenan, xanthan gum, sodium alginate,
Polysaccharides such as pullulan, methyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, carboxyvinyl polymer,
Other polymers such as polyvinylpyrrolidone and other synthetic polymers; extenders such as titanium oxide, kaolin, mica, sericite, zinc white, talc, and pigments such as polymer powders such as polymethylmethacrylic acid and nylon powder. Can be appropriately blended within a range that does not impair the effects of the present invention.

The cosmetic of the present invention can be produced by a usual method, and its dosage form can be any liquid form, creamy form, solid form, powder form, etc., but particularly liquid form. Alternatively, it is preferably creamy. The cosmetics of the present invention are preferably used for applications such as hair rinses and hair finishing agents such as hair conditioners. Particularly, when the cosmetics of the present invention are used as a hair finishing agent, good flexibility and smoothness on hair can be obtained. It is a good hair finishing agent that can be applied and has less greasiness and less oiliness.

[0034]

EFFECTS OF THE INVENTION The glyceryl ether-modified organo (poly) siloxanes (7A) to (11A) of the present invention form a liquid crystal in a water dispersion system, exhibit extremely excellent lubricity, and are resistant to almost all solvents. It is compatible and has the property of being easily dispersed almost uniformly when mixed with water. Therefore, it is a base for toiletries and cosmetics, emulsifiers, dispersants, wetting agents, solubilizers, liquid crystal forming agents, etc. It is extremely useful as

[0035]

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

Example 1

[0037]

[Chemical 14]

Glyceryl ether 11 represented by the formula (14)
g and 10 g of toluene were mixed and dissolved while raising the temperature to 70 ° C. 5.3 g of pentamethyldisiloxane represented by the formula (15) was added to this solution, chloroplatinic acid was added, and the mixture was aged at 70 ° C. for 3 hours. After completion of the reaction, toluene 50
g and activated carbon 1 g were added, and the mixture was stirred at 50 ° C. for 1 hour, and then the activated carbon and insoluble matter were separated by filtration. The filtrate was concentrated under reduced pressure to give the formula (16)
15.2 g of glyceryl ether-modified organodisiloxane represented by

¹ H-NMR (CDCl ₃ ), δ (ppm) −0.05: —CH ₂ —Si ( CH ₃ ) ₂ —O—Si (CH ₃ ) ₃ −0.02: —CH ₂ —Si (CH ₃ ). _{2 -O-Si (CH 3)} 3 0.40: - CH 2 -Si (CH 3) 2 -O-Si (CH 3) 3 1.18: -CH 2 - 3.46: -OCH 2 - 2.67: -C (CH 2 _{OH) 3 3.95: -OCH 2 -} CH (OH) -CH 2 O- example 2

[0040]

[Chemical 15]

Glyceryl ether 11 represented by the formula (17)
g and 10 g of toluene were mixed and dissolved while raising the temperature to 70 ° C. 5.3 g of pentamethyldisiloxane represented by the formula (15) was added to this solution, chloroplatinic acid was added, and the mixture was aged at 70 ° C. for 3 hours. After completion of the reaction, toluene 50
g and activated carbon 1 g were added, and the mixture was stirred at 50 ° C. for 1 hour, and then the activated carbon and insoluble matter were separated by filtration. The filtrate was concentrated under reduced pressure to give the formula (18)
15.2 g of glyceryl ether-modified organodisiloxane represented by

¹ H-NMR (CDCl ₃ ), δ (ppm) −0.05: —CH ₂ —Si ( CH ₃ ) ₂ —O—Si (CH ₃ ) ₃ −0.02: —CH ₂ —Si (CH ₃ ). _{2 -O-Si (CH 3)} 3 0.40: - CH 2 -Si (CH 3) 2 -O-Si (CH 3) 3 1.18: -CH 2 - 3.46: -OCH 2 - 2.77: - CH 2 OH 3.90 _{: -OCH 2 - CH (OH)} -CH 2 O- example 3

[0043]

[Chemical 16]

Glyceryl ether of the formula (14) 20.3
g and 20 g of toluene were mixed and dissolved while raising the temperature to 70 ° C. In this solution, 1,1, represented by formula (19)
1,3,5,5,5-heptamethyltrisiloxane 13.8
After adding g, chloroplatinic acid was added and aged at 70 ° C. for 3 hours. After completion of the reaction, 70 g of toluene and 1 g of activated carbon were added, and the mixture was stirred at 50 ° C. for 1 hour, then, the activated carbon and insoluble matter were separated by filtration. The filtrate was concentrated under reduced pressure to obtain 32.2 g of a glyceryl ether-modified organotrisiloxane represented by the formula (20).

¹ H-NMR (CDCl ₃ ), δ (ppm) −0.18: -CH ₂ -Si ( CH ₃ ) (-O-Si (CH ₃ ) ₃ ) ₂ -0.12: -CH ₂ -Si (CH _{3) (- O-Si (} C H 3) 3) 2 0.35: -C H 2 -Si (CH 3) (- O-Si (CH 3) 3) 2 1.18: -CH 2 - 3.46: -OCH 2 _{- 2.67: -C (C H 2} OH) 3 3.95: -OCH 2 - CH (OH) -CH 2 O- example 4

[0046]

[Chemical 17]

Glyceryl ether represented by the formula (17) 14.8
g and 15 g of toluene were mixed and dissolved while raising the temperature to 70 ° C. In this solution 1,1, represented by the formula (21)
After adding 3.74 g of 3,3,5,5,7,7-octamethyltetrasiloxane, chloroplatinic acid was added and the mixture was aged at 70 ° C for 3 hours. After the reaction, toluene 40g, activated carbon 1g
Was added and the mixture was stirred at 50 ° C. for 1 hour, and then activated carbon and insoluble matter were filtered off. The filtrate was concentrated under reduced pressure to obtain 21.2 g of glyceryl ether-modified organotetrasiloxane represented by the formula (22).

¹ H-NMR (CDCl ₃ ), δ (ppm) −0.19: —CH ₂ —Si ( CH ₃ ) ₂ — (O—Si (CH ₃ ) ₂ ) ₂ —O—Si ( CH ₃ ) ₂ -CH <sub>2
- 0.37: -CH 2 -Si (CH</sub> 3) 2 - (O-Si (CH 3) 2) 2 -O-Si (CH 3) 2 -CH 2 - 0.40: -C H 2 -Si (CH 3) _{2 - (O-Si (CH} 3) 2) 2 -O-Si (CH 3) 2 -C H 2 - 1.18: -CH 2 - 3.46: -OCH 2 - 2.77: -C H 2 OH 3.90: -OCH ₂ - CH (OH) -CH ₂ O- Example 5

[0049]

[Chemical 18]

Glyceryl ether 15.3 represented by formula (14)
g and 15 g of toluene were mixed and dissolved while raising the temperature to 70 ° C. In this solution, 1,1, represented by formula (23)
After adding 7.0 g of 1,3,5,7,7,7-octamethyltetrasiloxane, chloroplatinic acid was added and the mixture was aged at 70 ° C for 3 hours. After the reaction, toluene 40g, activated carbon 1g
Was added and the mixture was stirred at 50 ° C. for 1 hour, and then activated carbon and insoluble matter were filtered off. The filtrate was concentrated under reduced pressure to obtain 22.0 g of glyceryl ether-modified organotetrasiloxane represented by the formula (24).

¹ H-NMR (CDCl ₃ ), δ (ppm) −0.19: (CH ₃ ) ₃ Si- (O-Si (C H ₃ ) (CH _2- )) ₂ —O-Si (CH ₃ ) _{3 -0.12: (C H 3)} 3 Si- (O-Si (CH 3) (CH 2 -)) 2 -O-Si (C H 3) 3 0.40: (CH 3) 3 Si- (O-Si _{(CH 3) (C H 2} -)) 2 -O-Si (CH 3) 3 1.18: -CH 2 - 3.46: -OCH 2 - 2.67: -C (C H 2 OH) 3 3.95: -OCH 2 - CH (OH) -CH ₂ O- Example 6

[0052]

[Chemical 19]

Glyceryl ether 4.1 represented by the formula (17)
g and toluene 5 g were mixed and dissolved while raising the temperature to 70 ° C. XF40- represented by the formula (25)
After adding 30 g of A5149 (manufactured by Toshiba Silicone Co., Ltd.), chloroplatinic acid was added and the mixture was aged at 70 ° C. for 3 hours. After completion of the reaction, 100 g of toluene and 1 g of activated carbon were added, and the mixture was stirred at 50 ° C. for 1 hour, and then the activated carbon and insoluble matter were separated by filtration. The filtrate was concentrated under reduced pressure to obtain 33.7 g of glyceryl ether-modified organopolysiloxane represented by the formula (26).

¹ H-NMR (CDCl ₃ ), δ (ppm) −0.03: Si—CH ₃ 0.39: CH ₂ —Si 1.18: —CH ₂ — 3.46: —OCH ₂ — 2.77: —C H ₂ OH 3.90: _{-OCH 2 - CH (OH) -CH} 2 O- example 7

[0055]

[Chemical 20]

Glyceryl ether of the formula (14) 8.1
g and toluene 7 g were mixed and dissolved while raising the temperature to 70 ° C. XF40- represented by the formula (27)
After adding 25 g of A2428 (manufactured by Toshiba Silicone Co., Ltd.), chloroplatinic acid was added and the mixture was aged at 70 ° C. for 3 hours. After the reaction was completed, add 70 g of toluene and 1 g of activated carbon, and add 1 at 50 ℃.
After stirring for hours, activated carbon and insoluble matter were filtered off. The filtrate was concentrated under reduced pressure to obtain 32.7 g of glyceryl ether-modified organopolysiloxane represented by the formula (28).

¹ H-NMR (CDCl ₃ ), δ (ppm) −0.03: Si—CH ₃ 0.40: CH ₂ —Si 1.19: —CH ₂ — 3.46: —OCH ₂ — 2.67: —C (C H ₂ OH _{) 3 3.95: -OCH 2 - CH} (OH) -CH 2 O- example 8

[0058]

[Chemical 21]

Glyceryl ether of the formula (17) 8.5
g and toluene 7 g were mixed and dissolved while raising the temperature to 70 ° C. XF40- represented by the formula (29)
After adding 20 g of A2606 (manufactured by Toshiba Silicone Co., Ltd.), chloroplatinic acid was added and the mixture was aged at 70 ° C. for 3 hours. After completion of the reaction, add 50 g of toluene and 1 g of activated carbon, and add 1 at 50 ° C.
After stirring for hours, activated carbon and insoluble matter were filtered off. The filtrate was concentrated under reduced pressure to obtain 28.3 g of glyceryl ether-modified organopolysiloxane represented by the formula (30).

¹ H-NMR (CDCl ₃ ), δ (ppm) −0.03: Si—CH ₃ 0.40: CH ₂ —Si 1.18: —CH ₂ — 3.46: —OCH ₂ — 2.77: —C H ₂ OH 3.90: -OCH ₂ - with CH (OH) polyethylene oxide-modified organopolysiloxane known -CH ₂ O-test example 1 glyceryl ether modified organo the present invention obtained in example 1 and 2 (poly) siloxanes and conventional Silicone oil (KF96A, manufactured by Shin-Etsu Chemical Co., Ltd.)
The emulsifying power of was tested by the following method. The results are shown in Table 1. <Emulsification test method> Add 0.5 g of silicone oil and 9.0 g of ion-exchanged water to a 20 ml test tube with a lid. After adding 0.5 g of the test compound, the test tube was vigorously shaken for 1 minute and then allowed to stand at room temperature to observe the emulsified state. The emulsified product is indicated by ○ and the separated product is indicated by ×.

[0061]

[Table 1]

Cosmetic Formulation Example 1 Using the glyceryl ether-modified organo (poly) siloxane of the present invention obtained in Examples 1 and 2, a hair rinse agent having the composition shown in Table 2 was prepared by the following method, and its rinse performance was evaluated. It investigated by the following method. The results are shown in Table 2.

<Method for producing hair rinse agent> To water heated to 70 ° C., each component dissolved by heating to the same temperature was added, stirred and mixed, and then cooled to room temperature with stirring to obtain a hair rinse agent. It was

<Rinse Performance Evaluation Method> 20 g (15 cm in length) of hair of a Japanese woman who has never been subjected to cosmetic treatment such as cold perm or bleach has been bundled, and this hair bundle is mainly composed of an anion activator. After washing with a commercial shampoo, 2g of hair rinse agent shown in Table 2 is uniformly applied, and then rinsed under running water for 30 seconds,
A towel was dried. This wet hair bundle was sensory-evaluated for softness, smoothness, and oiliness according to the following criteria. Evaluation criteria Flexibility ◎: Particularly excellent, ○: Good, △: Normal,
×: Inferior smoothness ◎: Particularly excellent, ○: Good, Δ: Normal,
×: Inferior oily feeling ◎: Particularly low, ○: Good, Δ: Normal, ×: High

[0065]

[Table 2]

─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Yoshiaki Fujikura 1-3-6 Fujimioka, Utsunomiya City, Tochigi Prefecture (56) Reference JP 64-16793 (JP, A) JP 5-156019 (JP, A) JP 57-149290 (JP, A) JP 4-108795 (JP, A) JP 4-134013 (JP, A) JP 5-112424 (JP, A) JP 2 -265926 (JP, A) JP 5-124936 (JP, A) JP 6-135817 (JP, A) JP 6-305933 (JP, A) JP 5-98016 (JP, A) ) JP-A-6-234858 (JP, A) JP-A-6-157236 (JP, A) JP-A-4-66513 (JP, A) European Patent Application Publication 92700 (EP, A1) European Patent Application Publication 321824 ( EP, A 1) (58) Fields investigated (Int.Cl. ⁷ , DB name) C08G 77/00-77/62 A61K 7/00-7/50 CA (STN) REGISTRY (STN)

Claims (4)

(57) [Claims] 1. One of the general formulas (7A) to (11A).
A glyceryl ether-modified organo (poly) siloxane represented by: [Chemical 1] [In the formula, R ^{3 to} R ¹³ are each alkyl having 1 to 22 carbon atoms.
A group, an alkoxy group or a phenyl group, a is 1 to 1000
, B, d, e are numbers from 0 to 1000, respectively, and A is the formula
(3) [Chemical formula 2] (R ¹ is a linear or branched alkylene group having 6 to 20 carbon atoms.
X, Y, Z are all hydroxymethyl groups or X is a
Droxymethyl group, one of Y and Z is hydroxyl group, the other is hydrogen source
Is a child). ] 2. A glyceryl ether-modified organo (poly) according to claim 1, which is a compound represented by the general formula (2).
Siloxane. [Chemical 3] [In the formula, R ² represents an alkyl group having 1 to 22 carbon atoms, an alkoxyl group, a phenyl group or a group represented by the above formula (3) ,
n represents a number of 0 to 1000, but 2n + 6 R ^{2 s} may be the same or different, and at least one is a group represented by the formula (3). ] 3. An organo (poly) siloxane represented by any one of formulas (7) to (11) is reacted with a compound represented by formula (5). Process for producing glyceryl ether-modified organo (poly) siloxane. [Chemical 4] [In the formula, R ^{3 to} R ¹³ , a, b, d and e have the same meanings as described above. ] [Chemical 5] [In the formula, R ^{1 ′} represents a linear or branched alkylene group having 4 to 18 carbon atoms, m represents 1, and X, Y and Z have the same meanings as described above. ] 4. A cosmetic comprising the glyceryl ether-modified organo (poly) siloxane according to claim 1.