JPH07238170A - Glyceryl-ether-modified organo(poly)siloxane, its production, and cosmetic containing same - Google Patents

Abstract

PURPOSE:To produce a (poly)siloxane which forms a liquid crystal in the form of an aqueous dispersion and is improved in lubricity, compatibility and temperature stability by reacting an organo(poly)siloxane with a specified compound. CONSTITUTION:A compound of formula I (wherein R<1> is a 2-36 C linear or branched alkylene; and m is 0 or 1) is reacted with 110mol, per mol of the compound of formula I, of a compound of formula II (wherein X, Y and Z are each H, hydroxyl or 1-5 C alkyl which may be substituted with hydroxyl) at 50-200 deg.C for 1-10hr in the presence of an alkali catalyst in the presence or absence of a solvent to obtain a compound of formula III. This compound is reacted with an organo(poly)siloxane having at least one group of formula IV as a structural element at 20-100 deg.C for 1-10hr in the presence of a transition metal catalyst in a solvent in an amount 0.5-10 times larger than that of the total weight of the starting materials to produce a glyceryl-ether-modified organo(poly)siloxane having at least one group of formula V as a structural element.

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, as a result of intensive studies, the present inventors have found that a glyceryl ether-modified organo (poly) siloxane containing a group represented by the following general formula (1) as a constituent element. , Has the characteristics of forming a liquid crystal in a water dispersion system, showing extremely excellent lubricity, being compatible with almost all solvents, and being easily dispersed almost uniformly when mixed with water. In addition, they have found that they have extremely excellent performance as never before in cosmetics bases, emulsifiers, lubricants, and liquid crystal forming agents, and completed the present invention.

That is, the present invention is a glyceryl ether-modified organo (poly) siloxane characterized by containing at least one group represented by the general formula (1) as a constituent, a method for producing the same, and a cosmetic containing the same. Is provided.

[0006]

[Chemical 5]

[Wherein R ¹ represents a linear or branched alkylene group having 2 to 36 carbon atoms, and X, Y and Z are the same or different and each is a hydrogen atom, a hydroxyl group, or a carbon atom which may be substituted with a hydroxyl group. The alkyl groups of the numbers 1 to 5 are shown. Hereinafter, 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.

The glyceryl ether-modified organo (poly) siloxane of the present invention may be any as long as it contains at least one group represented by the general formula (1) as a constituent element. In the general formula (1), R ¹ has 2 to 36 carbon atoms,
It preferably represents a linear or branched alkylene group of 6 to 20, and specifically, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene. , Heptadecylene, octadecylene, nonadecylene,
Eicosylene, heneicosylene, docosylene, tricosylene, tetracosylene, pentacosylene, hexacosylene, 2-ethylhexylene, 2-butyldecylene, 2
-Ethyldodecylene, 2-butyldodecylene, 2-ethyltetradecylene, 2-hexyldecylene, 2-butyltetradecylene, 2-ethylhexadecylene, 2-hexyldecylene, 2-butylhexadecylene, 2- Ethyl octadecylene, 2-hexyl tetradecylene, 2-
Octyldodecylene, 2-butyloctadecylene, 2-
Ethyl eicosylene, 2-hexyl hexadecylene, 2
-Octyl tetradecylene, 2-butyl eicosylene,
2-ethyldocosylene, 2-hexyloctadecylene,
2-octyl hexadecylene, 2-butyl docosylene,
2-ethyl tetracosylene, 2-hexyl eicosylene, 2-octyl octadecylene, 2-heptyl undecylene, 2- (1,3,3-trimethylbutyl) octylene, 2-decyl tetradecylene, 2-dodecyl hexade Siren, 2-tetradecyl octadecylene, 5,7,
7-trimethyl-2- (1,3,3-trimethylbutyl) octylene, and the following formula (6)

[0009]

[Chemical 6]

(In the formula, 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).

Further, the groups represented by X, Y and Z are the same or different and each represents a hydrogen atom, a hydroxyl group or an alkyl group having 1 to 5 carbon atoms which may be substituted with a hydroxyl group. Specific examples of the alkyl group having 1 to 5 carbon atoms include methyl, ethyl, propyl, butyl, pentyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl and hydroxypentyl.
In terms of the emulsifying power of silicone oil, X is a C 1-3 alkyl group having a hydroxyl group, and Y and Z are the same or different and each is a hydrogen atom, a hydroxyl group, or a C 1-3 alkyl group having a hydroxyl group. A group is preferable, and a group in which X, Y, and Z are all hydroxymethyl groups, a group in which X is a hydroxymethyl group, one of Y and Z is a hydroxyl group, and the other is a hydrogen atom are more preferable.

Further, the glyceryl ether-modified organo (poly) siloxane containing at least one group represented by the general formula (1) as a constituent is not particularly limited as long as it is an organo (poly) siloxane having at least one group. However, the structure in which the siloxane units are linearly connected, the structure in which the siloxane units are connected in a mesh, a mixed type structure thereof, and the like are not particularly limited. 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.

[0013]

[Chemical 7]

[In the formula, R ² is an alkyl group having 1 to 22 carbon atoms,
Alkoxyl group, phenyl group or the following formula (3)

[0015]

[Chemical 8]

A group represented by the formula (wherein R ¹ , X, Y and Z have the same meanings as described above), n represents a number from 0 to 1000, and 2n + 6 R ² are the same. Alternatively, they may be 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, alkoxyl group and 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 0 to 10
The number is 00, but within the range, 0 to 300 is preferable, and 0 to 50 is particularly preferable.

The glyceryl ether-modified organo (poly) siloxane (hereinafter abbreviated as glyceryl ether-modified organo (poly) siloxane (1)) containing at least one group represented by the general formula (1) as a constituent of the present invention is It is manufactured as follows. That is, it can be produced by reacting an organo (poly) siloxane containing at least one group represented by the general formula (4) as a constituent with a compound represented by the general formula (5).

[0018]

[Chemical 9]

[In the formula, R ^{1 ′} represents a linear or branched alkylene group having 1 to 34 carbon atoms, m represents 0 or 1, and X, Y,
Z has the same meaning as described above. The organo (poly) siloxane containing at least one group represented by the general formula (4) as a constituent used in the present invention is an organo (poly) siloxane having at least one group.
There is no particular limitation as long as it is a siloxane, and there is no particular limitation such as a structure in which siloxane units are linearly connected, a structure in which they are connected in a mesh, a structure in which they are connected in a ring, and a mixed type structure thereof. Preferred as such an organo (poly) siloxane are those represented by the following general formulas (7) to (11).

[0020]

[Chemical 10]

[Wherein, R ^{3 to} R ¹³ each represent an alkyl group (preferably an alkyl group having 1 to 22 carbon atoms), an alkoxy group (preferably an alkoxy group having 1 to 22 carbon atoms) or a phenyl group, and , b, d, e each represent a number from 0 to 1000. ] The organo (poly) represented by the above general formulas (7) to (11)
Specific examples of siloxane 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, 1,1,3,3,5,5,5- Heptamethyltrisiloxane, pentamethyldisiloxane, 1,1,
3,3-tetramethyldisiloxane, triethylsilane, diethylmethylsilane, 1,3-diphenyl-1,
3-dimethyldisiloxane, diphenylmethylsilane,
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, phenyldimethylsilane, triisopropylsilane, tri- Examples thereof include n-octylsilane and triphenylsilane.

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.

[0024]

[Chemical 11]

[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 the compound represented by the general formula (13) in an amount of 1 to 10 mol times are used without solvent or in a solvent such as dimethyl sulfoxide and 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, 1 mol of the compound represented by the general formula (12) is added to 1 molecule of the polyhydric alcohol. 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.

To carry out the production method of the present invention, at least one of the groups represented by the general formula (4) is used as a constituent element.
Of the organo (poly) siloxane and the compound represented by the general formula (5), if necessary, 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. 1 at 20 to 100 ° C
Allow them to react for 10 hours.

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 as a total amount of 10 ^{− It} is preferable to add ⁴ to 10 ^-6 times by mole. Further, the reaction ratio of the raw material organo (poly) siloxane and the compound represented by the general formula (5) can be appropriately determined according to the modification degree of the glyceryl ether-modified organo (poly) siloxane (1) as the target compound. Often,
Although not particularly limited, for example, the number of Si—H bonds in the starting organo (poly) siloxane is 5, and the five Si—H bonds are
When all of the H bonds are modified, 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 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 the glyceryl ether-modified organo (poly) siloxane (1) of the present invention.

The cosmetic of the present invention contains glyceryl ether-modified organo (poly) siloxane (1) as an essential component. The amount of glyceryl ether-modified organo (poly) siloxane (1) in the cosmetic of the present invention is 0.1 ~ 20
% By weight is preferred and 0.5-10% by weight is particularly preferred.

In the cosmetic of the present invention, in addition to the glyceryl ether-modified organo (poly) siloxane (1), components used in ordinary cosmetics such as ethylene glycol, diethylene glycol, triethylene glycol,
Further polyethylene glycols, propylene glycol, dipropylene glycol, further polypropylene glycols, 1,3-butylene glycol,
Butylene glycols such as 1,4-butylene glycol, glycerin, diglycerin, and more polyglycerins, sorbitol, mannitol, xylitol,
Maltitol and other sugar alcohols, glycerin ethylene oxide (hereinafter abbreviated as EO), propylene oxide (hereinafter abbreviated as PO) adduct, sugar alcohols E
O, PO adducts, saccharides such as galactose, glucose and fructose and their EO and PO adducts, maltose,
Polysaccharides such as lactose and polyhydric alcohols such as EO and PO adducts; hydrocarbons such as liquid paraffin, squalane, vaseline, solid paraffin, olive oil, jojoba oil, evening primrose oil, coconut oil, natural oils such as beef tallow, isopropyl Ester oils such as myristate, cetyl isooctanoate and neopentyl glycol dicaprate, silicone oils such as methyl silicone and methylphenyl silicone, oily components such as higher fatty acids such as isostearic acid and oleic acid; polyoxyethylene (hereinafter, Abbreviated as POE) 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. Preservatives, 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 conventional 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, and particularly when the cosmetics of the present invention are used as a hair finishing agent, they have good flexibility and smoothness on hair. And a good hair finishing agent that does not make the hair sticky and has little oiliness.

[0032]

EFFECT OF THE INVENTION The glyceryl ether-modified organo (poly) siloxane (1) of the present invention forms a liquid crystal in a water dispersion system, exhibits extremely excellent lubricity, and is compatible with almost all solvents. And, since it has a property of easily dispersing almost uniformly when mixed with water, it is extremely useful as a base for toiletries and cosmetics, an emulsifier, a dispersant, a wetting agent, a solubilizer, a liquid crystal forming agent, etc. It is a thing.

[0033]

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

[0035]

[Chemical 12]

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

[0038]

[Chemical 13]

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

[0041]

[Chemical 14]

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

[0044]

[Chemical 15]

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 2 - 0.37: -CH 2 -Si} (CH 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

[0047]

[Chemical 16]

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

[0050]

[Chemical 17]

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

[0053]

[Chemical 18]

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 (CH ₂ OH _{) 3 3.95: -OCH 2 - CH} (OH) -CH 2 O- example 8

[0056]

[Chemical 19]

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 ×.

[0059]

[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.

<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. Was washed with a commercially available shampoo, 2 g of the hair rinse agent shown in Table 2 was uniformly applied, and then rinsed with running water for 30 seconds, and then towel 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,
X: Inferior smoothness ◎: Particularly excellent, ○: Good, Δ: Normal,
X: Inferior oily feeling ◎: Particularly small, ○: Good, Δ: Normal, ×: Large

[0062]

[Table 2]

Claims (6)

[Claims] 1. A glyceryl ether-modified organo (poly) siloxane containing at least one group represented by the general formula (1) as a constituent element. [Chemical 1] [In the formula, R ¹ represents a linear or branched alkylene group having 2 to 36 carbon atoms, and X, Y, and Z are the same or different and each is a hydrogen atom, a hydroxyl group, or 1 to 12 carbon atoms which may be substituted with a hydroxyl group. 5 represents an alkyl group. ] 2. In the general formula (1), X is an alkyl group having 1 to 3 carbon atoms having a hydroxyl group, and Y and Z are the same or different and each is a hydrogen atom, a hydroxyl group, or 1 to 3 carbon atoms having a hydroxyl group. The glyceryl ether-modified organo (poly) siloxane according to claim 1, which is an alkyl group of 3. In the general formula (1), X, Y and Z are all hydroxymethyl groups, or X is a hydroxymethyl group,
The glyceryl ether-modified organo (poly) siloxane according to claim 1, wherein one of Y and Z is a hydroxyl group and the other is a hydrogen atom. 4. A glyceryl ether-modified organo (poly) according to claim 1, which is a compound represented by the general formula (2).
Siloxane. [Chemical 2] [Wherein R ² is an alkyl group having 1 to 22 carbon atoms, an alkoxyl group, a phenyl group or the following formula (3): (Wherein R ¹ , X, Y and Z have the same meanings as described above), and n is a number from 0 to 1000, but 2n + 6 R ² are the same or different. Alternatively, at least one is a group represented by the formula (3). ] 5. An organo (poly) siloxane containing at least one group represented by the general formula (4) as a constituent is reacted with a compound represented by the general formula (5). A process for producing the described glyceryl ether-modified organo (poly) siloxane. [Chemical 4] [In the formula, R ^{1 ′} represents a linear or branched alkylene group having 1 to 34 carbon atoms, m represents 0 or 1, and X, Y and Z have the same meanings as described above. ] 6. A cosmetic comprising the glyceryl ether-modified organo (poly) siloxane according to claim 1.