JP3478607B2 - Manufacturing method of treated powder - Google Patents

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing a treated powder, and more particularly to a method for adding a Si-H group reactive compound to a powder coated with a Si-H group-containing silicone compound. The present invention relates to a method for producing a safe and stable treated powder that is environmentally safe and has a reduced production cost by using substantially only water without using an organic solvent as a reaction solvent.

The treated powder produced by the present invention is not only used as a colorant in the fields of paints, inks, cosmetics, medical materials, etc., but also as a magnetic material, a column packing for gas chromatographs, a catalyst, etc. Can be widely used.

[0003]

2. Description of the Related Art In the fields of paints, inks, cosmetics, magnetic materials, medical materials, etc., modified powders are often used in which functional groups are introduced into powders to impart various characteristics and functions. ing.

Conventionally, when a functional group is introduced into powder,
Generally, silane coupling agents have been used. However, when the modified powder thus obtained is mixed with cosmetics or the like, problems such as deterioration or odor may occur, or problems such as deterioration or decomposition of other coexisting components may occur. It was

On the other hand, the present applicant has already coated the powder with a silicone polymer film having a Si--H group, and
A powder having improved properties (for example, hydrophobicity and stability) while maintaining the original properties of the powder by adding a compound capable of reacting with an i-H group to the Si-H group of the silicone polymer. They have found that a body can be obtained, and have completed the invention of a modified powder (Japanese Patent Publication No. 1-54380). Here, the addition reaction of the above Si-H group-reactive compound to the Si-H group of the silicone polymer is generally known as a hydrosilylation reaction, and usually a reaction solvent such as isopropyl alcohol (IPA), dioxane and toluene is used. An organic solvent is used. In addition, JP-A-1-11
Japanese Patent No. 0540 discloses a production method in which the above addition reaction is carried out using a reaction solvent containing water (water: ethanol = 1: 1).

However, when an organic solvent such as dioxane or toluene is used in the hydrosilylation reaction, it remains in the treated powder and is difficult to remove. In addition, these solvents have a problem in that after the use, the wastewater treatment requires a lot of economical and work burdens in terms of environmental measures and treatment. Further, even if water is contained in the reaction solvent, the above problems cannot be completely solved to some extent.

[0007]

SUMMARY OF THE INVENTION The present invention has been made in view of the above circumstances, and an object thereof is Si-
Si is added to the powder coated with the silicone compound having H group.
It is an object of the present invention to provide a method for producing a modified powder by adding a -H-reactive compound, which is environmentally safe, has a reduced production cost, and is a safe and stable method for producing a treated powder.

[0008]

As a result of intensive studies by the present inventors, not only the above problems can be solved by using substantially only water as a solvent during the hydrosilylation reaction, but also the reaction rate can be improved. Based on this finding, the present invention was completed based on the finding that the high addition density can be achieved as well as or better than the conventional one.

That is, the present invention provides a treated powder obtained by coating a powder with a silicone compound having a Si-H group and then adding a compound capable of reacting with the Si-H group to the Si-H group portion of the silicone compound. In the method for producing a body, there is provided a method for producing a treated powder, characterized in that the addition is carried out using substantially only water as a reaction solvent.

Further, the present invention provides a method for producing a product using the treated powder obtained by the above production method, particularly a method for producing a cosmetic composition, a coating composition and a resin molded product (container, etc.). is there.

The treated powder obtained according to the present invention is stable, has no interaction with a drug, and has no decomposing action on a fragrance. Therefore, when it is used as a drug, a cosmetic, etc., its stability with time is remarkably improved. To do. In addition, since the addition density of the compound capable of reacting with the Si-H group (Si-H group-reactive compound) to the powder is high, the dispersibility can be controlled. Therefore, the magnetic powder is treated by the method of the present invention. As a result, an excellent magnetic material can be obtained. Furthermore, by increasing the addition density, the separation of the column chromatographic packing material can be increased and the number of theoretical plates can be significantly increased. Therefore, use it for gas chromatographic column packing material, liquid chromatographic column packing material, etc. You can

According to the present invention, the use of substantially only water as a reaction solvent allows the non-polar Si-H group-reactive compound to be distributed at a high concentration on the surface of the silicone-coated powder, and the like. It is thought that various effects can be obtained. Therefore, it is particularly effective for the hydrosilylation reaction of the Si-H group-reactive compound having a polar group.

The present invention will be described in detail below.

The powder used in the present invention is not particularly limited, but generally means any object having a particle size of 10 mm or less (some may have a particle size larger than 10 mm), and specifically, Examples thereof include organic pigments, inorganic pigments, metal oxides and hydroxides, mica, pearl luster materials, metals, carbon, magnetic powders, silicate minerals, and porous materials. These powders may be used alone or in combination of two or more, and may be an aggregate, a molded body or a shaped body. Also on or in the powder other substances (eg colorants, UV absorbers, pharmaceuticals,
Various additives) may be contained. According to the present invention, it is possible to modify (treat) any powder including ultrafine powder having a particle size of 0.02 μm or less.

Examples of organic pigments include Red No. 201,
Red No. 202, Red No. 204, Red No. 205, Red No. 22
No. 0, Red 226, Red 228, Red 305, Orange 203, Orange 204, Yellow 205, Yellow 401
No. and Blue No. 404, and Red No. 3 and Red 104
No. 106, Red No. 106, Red No. 227, Red No. 230, Red No. 401, Red No. 505, Orange No. 205, Yellow No. 4, Yellow No. 5, Yellow No. 202, Yellow No. 203, Green No. 3 and Blue No. 1 etc. Further, these organic pigments may be zirconium lake, barium lake, aluminum lake or the like.

Examples of the inorganic pigments include dark blue, ultramarine blue, manganese violet, (oxidized) titanium-coated mica, bismuth oxychloride and the like.

The metal oxide and metal hydroxide include
For example, magnesium oxide, magnesium hydroxide, calcium oxide, calcium hydroxide, aluminum oxide, aluminum hydroxide, silica, iron oxide (α-Fe ₂ O ₃ , γ
-Fe ₂ O ₃ , Fe ₃ O ₄ , FeO, etc.), yellow iron oxide (particularly rod-shaped), red iron oxide, black iron oxide, iron hydroxide, titanium oxide (particularly 0.001 to 0.1 μm in particle size) Titanium dioxide), low-order titanium oxide, zirconium oxide, chromium oxide, chromium hydroxide, manganese oxide, cobalt oxide, nickel oxide, and composite oxides and hydroxides of a combination of two or more thereof, such as silica alumina. , Iron titanate, cobalt titanate, lithium cobalt titanate, cobalt aluminate and the like.

Examples of the mica include muscovite, phlogopite, biotite, sericite, phlogopite, phlogopite, lithia mica, chinwald micas, soda micas, artificial micas, and KAl ₂ (A).
1, Si ₃ ) O ₁₀ F ₂ , KMg ₃ (Al, Si ₃ ) O ₁₀
Examples thereof include mica represented by F ₂ , K (Mg, Fe ₃ ) (Al, Si ₃ ) O ₁₀ F ₂ .

The pearl luster material is, for example, a mica titanium-based composite material, a mica iron oxide-based composite material, bismuth oxychloride, guanine, or a titanium compound containing titanium oxynitride and / or lower titanium oxide. Mica and the like. The titanium of the mica titanium-based composite material may be any of titanium dioxide, low-order titanium oxide, and titanium oxynitride. Further, mica titanium-based composite material or bismuth oxychloride, for example, iron oxide,
It may be a mixture of dark blue, chrome oxide, carbon black, carmine, ultramarine or the like.

Examples of the metal include aluminum, iron,
Examples include nickel, cobalt, chromium, gold, silver, copper, platinum, zinc, indium, tin, antimony, tungsten, zirconium, molybdenum, silicon and titanium.

As the magnetic powder, for example, γ-Fe ₂ O
₃ , magnetite (Fe ₃ O ₄ ), beltrite iron oxide (FeO _x 1.33 <x <1.5) or those modified with cobalt, manganese, nickel, zinc, chromium, etc., or needle-shaped Iron or Al, B, Co, Cr,
Examples thereof include iron powder containing Cu, Mo, Mn, Ni, P, Si, Sn, and Zn, CrO ₂ and Ba ferrite.

The powder may be iron, nickel, cobalt or an oxide thereof coated on mica,
It is not limited to this.

The silicate minerals are phyllosilicate minerals (for example, kaolin group, montmorillonite group, clay mica group, chlorite group, serpentine group) and tectosilicate minerals (for example, zeolite group), and pyrophyllite. , Talc, chlorite, chrysotile, antigorite, lizardite, kaolinite, deckite, nacrite, halosite, montmorillonite, nontronite, saponite, sauconite, bentonite, soda, medium zeolite, scolesite, Thomsonite, etc. Examples thereof include soluteite, heulandite, stilbite, chabazite and other heulites, and zeolites such as halonite, heavy hepatite, olivine, chabazite and gmelinite.

Further, in the present invention, the treatment of the porous material can be favorably carried out. Examples of the porous material include porous glass beads, hollow silica or zeolite, metal oxides, metal nitrides and silicates. Minerals, carbonate minerals, sulfate minerals or phosphate minerals that have been granulated or molded, or those that have been granulated or molded and then calcined, metals, cellulose, fibers, synthetic resins, etc. You can

In the present invention, as the first step, the powder is coated with a silicone compound having a Si--H group. As this silicone compound, any compound can be used as long as it has a Si-H group, but the compound of the general formula (I) is preferred.

[0026]

[Chemical 5] [In the formula, R ¹ , R ² and R ³ are each independently a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms and substitutable with at least one halogen atom (provided that R ¹ ,
R ² and R ³ are not hydrogen atoms at the same time); R
⁴ , R ⁵ and R ⁶ are each independently a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which can be substituted with at least one halogen atom; a is 0 or an integer of 1 or more, b is 0 or an integer of 1 or more, c is 0 or 2 (provided that 3 ≦ a + b + c ≦ 10000); and this compound is assumed to contain at least one Si—H group moiety]. Silicone compounds can be used.

When c = 0, the following general formula (I
II)

[0028]

[Chemical 6] [Wherein R ¹ , R ² , R ³ , a and b are as defined above. However, preferably, R ¹ , R ² and R ³ independently of each other are at least one halogen atom (especially fluorine atom).
A lower alkyl group or an aryl group (for example, a phenyl group) having 1 to 4 carbon atoms that can be substituted with a; a + b is 3 or more, preferably 3 to 100, and particularly 3 to 7] It is a silicone compound. It is preferable that one molecule has two or more hydrogen atoms. In addition, if there are too many hydrogen atoms, it is difficult to obtain because there are two silicon atoms bonded to a silicon atom. Specific examples of the compound of the general formula (III) include hexamethylcyclotetrasiloxane, pentamethylcyclotetrasiloxane, tetramethylcyclotetrasilotetrasiloxane, octamethylcyclopentasiloxane, heptamethylcyclopentasiloxane, and hexamethylcyclopentasiloxane. Siloxane, pentamethylcyclopentasiloxane, methyl hydrogen polysiloxane (molecular weight 60
00) and the like.

When c = 2, the following general formula (I
V)

[0030]

[Chemical 7] [Wherein R ^{1 to} R ⁶ , a and b are as defined above. However, R ^{1 to} R ⁶ are preferably at least 1 independently of each other.
A lower alkyl group having 1 to 4 carbon atoms or an aryl group (for example, a phenyl group) which can be substituted with one halogen atom (particularly a fluorine atom); a + b is 1 to 100, particularly 2 to 5
Is a chain silicone compound represented by Specific examples of the general formula (IV) include 1,1,1,3,5,
7,7,7-octamethyltetrasiloxane, 1,1,
1,3,5,7,9,9,9-nonamethylpentasiloxane, and 1,1,1,3,5,7,9,11,1
1,11-decamethylhexasiloxane, 1,3,5
Examples thereof include 7-tetramethylcyclotetrasiloxane.

Each of the above siloxanes has a relatively low boiling point and is suitable for gas phase treatment. When coating the powder in a liquid phase or a solid phase, it is preferable that 10 ≦ (a + b + c) ≦ 200. The coating amount of the silicone compound is preferably about 0.01 to 30%, more preferably 0.1 to 10%, based on the powder.

The powder coating method of the above Si—H group-containing silicone compound can be carried out by various methods including conventional coating methods and is not particularly limited.

For example, the above silicone compound is dissolved in an organic solvent (chloroform, hexane, benzene, toluene, acetone, etc.) and powder is dispersed therein to prepare a dispersion liquid, which is then heated. The powder can be coated with a film of the silicone compound by evaporating the solvent and forming a film on the surface of the powder. Alternatively, by pouring the dispersion into a poor solvent of the silicone compound, or by pouring a poor solvent into the dispersion and depositing the insolubilized silicone compound on the surface of the powder to form a film, the powder is formed. The body may be covered. Or
The powder may be coated by mechanochemically treating the liquid silicone compound and the powder in, for example, a ball mill. Further, the powder may be encapsulated with a film of the silicone compound by polymerizing the silicone compound monomer in the presence of a catalyst on the surface of the powder, as in the in-situ polymerization method. Alternatively, active sites that are widely distributed on substantially the entire surface of the powder can be used for coating.

The thus obtained silicone-coated powder has an unreacted Si-H group portion, and becomes slightly unstable under severe conditions such as alkali and acid.

Next, in the second step, the unreacted Si-H group of the silicone compound coated with the above-mentioned powder is added to this Si-H.
A compound capable of reacting with the group is added. This allows S to react with the unreacted Si-H portion of the silicone compound.
The i-H reactive compound is added to introduce a pendant group derived from the Si-H reactive compound into the silicone compound. Various functions can be imparted to the powder by appropriately selecting the Si—H reactive compound and introducing a desired pendant group.

To further describe this, the above-mentioned first
In the coating step of the step, cross-linking of Si-H groups occurs on the powder surface to form a stitch structure, and the powder surface is coated with a film of a silicone compound, but the cross-linking is completely completed due to steric hindrance or the like. Not done Therefore, residual Si-H groups are present and tend to be slightly unstable under severe conditions such as alkali and acid. This residual Si-H group has Si-H
A reactive compound (for example, an unsaturated compound such as an alkene or an alkyne) is added by a hydrosilylation reaction,
By forming a Si—C bond, it is possible to obtain a powder that is more stable to alkalis and acids.

Therefore, various functions can be imparted to the powder by appropriately selecting the Si—H reactive compound (unsaturated compound, etc.) and introducing a desired pendant group. Here, the "pendant group" means a residue of a compound capable of reacting with the Si-H group portion and is introduced into the silicone polymer by an addition reaction of the compound. This pendant group imparts various properties and functions to the powder. The hydrophobicity can be further enhanced by adjusting the type or length of the hydrocarbon group of the unsaturated compound to be added.

The compound used in the addition reaction is S
Any compound can be optionally used as long as it is a compound capable of reacting with the i-H group. As such a compound, for example, a compound having an OH group or an SH group such as an amino acid (such as cysteine) can be used.
Further, at least one carbon-carbon double bond or triple bond.
It is possible to use an unsaturated compound (vinyl compound) which has an individual group and can react with the Si-H group moiety.

Suitable unsaturated compounds include compounds of the general formula (I
I)

[0040]

[Chemical 8] {In the formula, R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are independently of each other a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, an acyloxy group, an alkoxy group, an amino group, a nitro group, a carboxyl group, a sulfo group, or a carbon atom. A substituted or unsubstituted hydrocarbon group of the number 1 to 30 [eg, aliphatic group (eg, alkyl group, alkenyl group, alkynyl group), aromatic group (eg, phenyl group, naphthyl group), heterocyclic group (eg, hetero atom) A compound containing at least one nitrogen atom, oxygen atom or sulfur atom), an alicyclic group (eg cycloalkyl group, cycloalkenyl group, cycloalkynyl group), spiro compound residue or terpene compound residue] ;
Alternatively, R ¹¹ and R ¹³ form a carbon-carbon bond, and -C =
Can be combined with C- to form -C≡C-;
Alternatively, R ¹² and R ¹⁴ form a carbon-carbon bond, and -C =
Can form an alicyclic group together with C-}
And the like.

The hydrocarbon groups R ^{11 to} R ¹⁴ have the general formula (I
One or more unsaturated hydrocarbon groups (eg those exemplified in the definition of general formula (II) above) and / or unless they adversely affect the addition reaction by double or triple bonds in the compounds of I) It can be substituted with one or more functional groups. Representative examples of the functional group include a halogen atom, an amino group, a carboxyl group, a sulfo group, a mercapto group, an epoxy group, a cyano group, a nitro group, a hydroxyl group, an alkoxy group, an alkoxycarbonyl group, an acyl group, an acyloxy group, and a quaternary ammonium group. Group, polyalkylene ether group and the like.

A more preferred unsaturated compound has an unsaturated bond (double bond or triple bond) at the terminal or at any position.
Alkenes or alkynes having more than one, such as acetylene, ethylene, propylene, butene, octene,
Examples include decene and octadecene. Alken, etc.
If it has an unsaturated bond, it undergoes an addition reaction with the Si-H moiety at that position, so a cyclic structure such as cyclohexane, benzene, or naphthalene may be present at any other position.

It is also possible to use butadiene, isoprene or the like having two or more double bonds.

In the present invention, the Si--H group-reactive compound is used as the silicone compound Si for coating the powder.
It is characterized in that when it is added to the —H group, substantially only water is used as a reaction solvent. Conventionally, an addition reaction was carried out using an organic solvent such as IPA, dioxane, or toluene as the reaction solvent, but these solvents remain in the treated powder and are difficult to remove, and such treated powder is used as it is. There is a safety issue, or
In terms of environmental measures, wastewater treatment after the use of a solvent imposes a large economic burden on the treatment. Even when water was used as the reaction solvent, the above problems still remained to some extent. However, in the present invention, since the addition reaction is performed using substantially only water without using these organic solvents as the reaction solvent, there are problems in terms of safety and environmental measures such as waste liquid treatment. Can be resolved. Further, by using water instead of the organic solvent, the manufacturing cost of the treated powder can be reduced. Furthermore, since the reaction time, the addition density, etc. can be performed as good as or better than those in the conventional case, good results can be obtained especially in the production efficiency and product quality of the final product and the like.

The addition reaction is carried out, for example, as follows.

First, the treated powder that has undergone the coating process in the first stage is mixed with a solvent (water). Since the treated powder is hydrophobic and is not easily dispersed, stirring is performed at a relatively high rotation speed. As a result, the water and the powder begin to mix while gradually entraining air, and finally a whipped cream is formed. After that, for example, a Si—H group-reactive compound such as an unsaturated compound (vinyl compound) is added in a liquid state and well stirred. After the vinyl compound is well mixed, the catalyst is added. After that, temperature rise (30
A treated powder (modified powder) to which a desired vinyl compound is added can be obtained by stirring at 0 ° C. or lower, preferably 0 to 250 ° C. and stirring for a predetermined time (preferably 1 hour or more). The addition reaction may be carried out in a gas phase, a liquid phase or a solid phase depending on the Si-H group-reactive compound used and the like.
It can also be performed by using ultraviolet rays, γ rays, plasma, or the like.

As the catalyst used in the above addition reaction, platinum group catalysts, that is, compounds of ruthenium, rhodium, palladium, osmium, iridium and platinum are suitable, and compounds of palladium and platinum are particularly suitable. Examples of the palladium type include palladium (II) chloride, ammonium tetraaminepalladium (II) chloride chloride, palladium (II) oxide, and palladium (II) hydroxide. In the platinum system, platinum (II) chloride, tetrachloroplatinic acid (II), platinum (IV) chloride, hexachloroplatinic acid (IV), ammonium hexachloroplatinate (IV),
Platinum (II) oxide, platinum (II) hydroxide, platinum (IV) dioxide, platinum (IV) oxide, platinum (IV) disulfide, platinum (IV) sulfide, potassium hexachloroplatinate (IV) acid and the like can be mentioned. In addition, amine catalysts such as tributylamine or polymerization initiators can be used.

Further, according to the present invention, a method for producing a product such as a cosmetic composition, a coating composition, a resin molded product (a container by injection molding, etc.) using the treated powder obtained by the above-mentioned production method. Will be provided. In the method for producing these products, each product can be produced by a conventional method except that the treated powder produced by the above-described production method of the present invention is used in place of the treated powder produced by the conventional method.
By using the treated powder obtained by the production method of the present invention, the final product such as a cosmetic composition, a coating composition, a container can be manufactured at a reduced production cost, improved in product quality, stable in product and safe. It is possible to reduce the economic and work burdens in terms of performance and environmental measures.

When the present inventors carried out the addition reaction of the vinyl compound using only water as a solvent, they were able to achieve the same reaction rate and addition density as when an organic solvent was used. Hereinafter, the present invention will be described in more detail with reference to examples. However, it goes without saying that the scope of the present invention is not limited to these examples.

[0050]

EXAMPLES Example 1-1: Silicone Polymer of Fine Particle Silica Gel
Particle size 5 in the rotary double cone type reactor coating volume 100 liters (stainless steel, with insulation jacket)
4 kg of 0 nm silica gel was added. The temperature of the reaction tank and the processing liquid supply tank (stainless steel, with a heat insulation jacket) directly connected to it with a volume of 10 liters, the heat medium heated to 80 ° C. is supplied from the heat medium heating tank to each heat insulation jacket by a circulation pump. By doing, 80 ℃
Held in. Nitrogen gas was supplied to the treatment liquid supply tank at 1.5 l / min to bubble the treatment liquid (1,3,5,7-tetramethylcyclotetrasiloxane). A condenser was attached to the reaction tank so that nitrogen gas was released from the condenser and unreacted treating agent could be recovered. Further, the reaction tank was rotated at 10-minute intervals for 1 minute, and the operation of mixing the fine particle silica gel in the reaction tank was repeated for 8 hours to take out the treated powder. The powder obtained showed a marked hydrophobicity.

Example 1-2 The same treatment was carried out by replacing the fine particle silica gel of Example 1-1 with fine particle titanium dioxide to obtain a silicone polymer-coated fine particle titanium dioxide.

Example 1-3 10 kg of fine particle silica gel of Example 1-1 was added to sericite.
Instead of the above, the same treatment was carried out to obtain a silicone polymer-coated sericite.

Example 1-4 The same procedure was carried out by substituting 10 kg of talc for the fine particle silica gel of Example 1-1 to obtain a silicone polymer-coated talc.

Example 1-5 The fine particle silica gel of Example 1-1 was mixed with 10 kg of titanium mica.
Instead of the above, the same treatment was performed to obtain a silicone polymer-coated titanium mica.

Examples 1-6 20 g of fine particle titanium dioxide was placed in a planetary ball mill and 5
After mixing and milling for 1 minute, 1 g of methyl hydrogen polysiloxane (molecular weight 6000) was added and further mixed and milled for 3 hours. The resulting treated powder showed a marked hydrophobicity.

Example 1-7 The particulate titanium dioxide of Example 1-6 was replaced with sericite and the same treatment was carried out to obtain a silicone polymer-coated sericite.

Example 1-8 The particulate titanium dioxide of Example 1-6 was replaced with particulate silica gel and the same treatment was carried out to obtain a silicone polymer-coated silica gel.

Example 1-9 The fine particle titanium dioxide of Example 1-6 was replaced with zinc white,
The same treatment was performed to obtain a silicone polymer-coated zinc oxide.

Example 2-1: Silicon Polymer Coated Fine
Surface modification of particle silica gel 100 g of the silicone polymer-coated fine particle silica gel of Example 1-1 is placed in a 3-liter eggplant-shaped flask, 300 g of water is added thereto, and high speed stirring is performed with a stirrer for 10 to 15 minutes.
It was made for a minute and whipped. Next, 7 g of 2-hydroxy-3-allyl-4-methoxybenzophenone was dissolved and added, 10 mg of chloroplatinic acid was further added as a catalyst, and the mixture was stirred and heated in a mantle heater at 80 ° C. for 6 hours, filtered, and then It was washed with 2 liters of ethanol and degassed and dried to obtain a treated powder surface-modified with benzophenone.

Example 2-2 Using the silicone polymer-coated fine particle titanium dioxide of Example 1-2, the same surface modification as in Example 2-1 was performed to obtain a treated powder.

Example 2-3 Using the silicone polymer-coated sericite of Example 1-3, the same surface modification as in Example 2-1 was carried out to obtain a treated powder.

Example 2-4 The same surface modification as in Example 2-1 was carried out using the silicone polymer-coated talc of Example 1-4 to obtain a treated powder.

Example 2-5 Using the silicone polymer-coated titanium mica of Example 1-5, the same surface modification as in Example 2-1 was performed to obtain a treated powder.

Example 2-6 Using the silicone polymer-coated fine particles of titanium dioxide of Example 1-6, the same surface modification as in Example 2-1 was carried out to obtain a treated powder.

Example 2-7 The same surface modification as in Example 2-1 was carried out using the silicone polymer-coated sericite of Example 1-7 to obtain a treated powder.

Example 2-8 Using the silicone polymer-coated fine particle silica gel of Example 1-8, the same surface modification as in Example 2-1 was carried out to obtain a treated powder.

Example 2-9 Using the silicone polymer-coated zinc white of Example 1-9, the same surface modification as in Example 2-1 was performed to obtain a treated powder.

Example 3-1 Using the silicone polymer-coated fine particle silica gel of Example 1-1, the same operation as in Example 2-1 was carried out.
Treatment with 4,5-trimethoxycinnamate gave a treated powder.

Example 3-2 The surface modification was carried out in the same manner as in Example 3-1 using the silicone polymer-coated fine particle titanium dioxide of Example 1-2 to obtain a treated powder.

Example 3-3 Using the silicone polymer-coated sericite of Example 1-3, the same surface modification as in Example 3-1 was carried out to obtain a treated powder.

Example 3-4 Using the silicone polymer-coated talc of Example 1-4, the same surface modification as in Example 3-1 was carried out to obtain a treated powder.

Example 3-5 Using the silicone polymer-coated titanium mica of Example 1-5, the same surface modification as in Example 3-1 was performed to obtain a treated powder.

Example 3-6 The same surface modification as in Example 3-1 was performed using the silicone polymer-coated fine particle titanium dioxide of Example 1-6 to obtain a treated powder.

Example 3-7 Using the silicone polymer-coated sericite of Example 1-7, the same surface modification as in Example 3-1 was performed to obtain a treated powder.

Example 3-8 Using the silicone polymer-coated fine particle silica gel of Example 1-8, the same surface modification as in Example 3-1 was carried out to obtain a treated powder.

Example 3-9 Using the silicone polymer-coated zinc oxide of Example 1-9, the same surface modification as in Example 3-1 was carried out to obtain a treated powder.

Example 4-1 Using the silicone polymer-coated fine particle silica gel of Example 1-1, the same operation as in Example 2-1 was carried out to give 2- (2-hydroxy-3-allyl-5-methylphenyl) benzo. Triazine was used to obtain a treated powder.

Example 4-2 Using the silicone polymer-coated fine particles of titanium dioxide of Example 1-2, the same surface modification as in Example 4-1 was carried out to obtain a treated powder.

Example 4-3 The same surface modification as in Example 4-1 was carried out using the silicone polymer-coated sericite of Example 1-3 to obtain a treated powder.

Example 4-4 Using the silicone polymer-coated talc of Example 1-4, the same surface modification as in Example 4-1 was carried out to obtain a treated powder.

Example 4-5 Using the silicone polymer-coated titanium mica of Example 1-5, the same surface modification as in Example 4-1 was carried out to obtain a treated powder.

Example 4-6 The same surface modification as in Example 4-1 was performed using the silicone polymer-coated fine particle titanium dioxide of Example 1-6 to obtain a treated powder.

Example 4-7 Using the silicone polymer-coated sericite of Example 1-7, the same surface modification as in Example 4-1 was carried out to obtain a treated powder.

Example 4-8 Using the silicone polymer-coated fine particle silica gel of Example 1-8, the same surface modification as in Example 4-1 was carried out to obtain a treated powder.

Example 4-9 Using the silicone polymer-coated zinc white of Example 1-9, the same surface modification as in Example 4-1 was carried out to obtain a treated powder.

Example 5-1 Using the silicone polymer-coated fine particle silica gel of Example 1-1, the same operation as in Example 2-1 was carried out with 4-allyloxy-4′-t-butylbenzoylmethane, and the treatment was carried out. A powder was obtained.

Example 5-2 Surface treatment was performed in the same manner as in Example 5-1 using the silicone polymer-coated fine particle titanium dioxide of Example 1-2 to obtain a treated powder.

Example 5-3 Using the silicone polymer-coated sericite of Example 1-3, the same surface modification as in Example 5-1 was carried out to obtain a treated powder.

Example 5-4 Using the silicone polymer-coated talc of Example 1-4, the same surface modification as in Example 5-1 was carried out to obtain a treated powder.

Example 5-5 Using the silicone polymer-coated titanium mica of Example 1-5, the same surface modification as in Example 5-1 was performed to obtain a treated powder.

Example 5-6 The same surface modification as in Example 5-1 was performed using the silicone polymer-coated fine particles of titanium dioxide of Example 1-6 to obtain a treated powder.

Example 5-7 The same surface modification as in Example 5-1 was carried out using the silicone polymer-coated sericite of Example 1-7 to obtain a treated powder.

Example 5-8 Using the silicone polymer-coated fine particle silica gel of Example 1-8, the same surface modification as in Example 5-1 was carried out to obtain a treated powder.

Example 5-9 Using the silicone polymer-coated zinc white of Example 1-9, the same surface modification as in Example 5-1 was carried out to obtain a treated powder.

Example 6-1 Using the silicone polymer-coated fine particle silica gel of Example 1-1, the same operation as in Example 2-1 was carried out with tetradecene to obtain a treated powder surface-modified with a tetradecyl group. It was

Example 6-2 The same surface modification as in Example 6-1 was carried out using the silicone polymer-coated fine particles of titanium dioxide of Example 1-2 to obtain a treated powder.

Example 6-3 The same surface modification as in Example 6-1 was carried out using the silicone polymer-coated sericite of Example 1-3 to obtain a treated powder.

Example 6-4 Using the silicone polymer-coated talc of Example 1-4, the same surface modification as in Example 6-1 was carried out to obtain a treated powder.

Example 6-5 Using the silicone polymer-coated titanium mica of Example 1-5, the same surface modification as in Example 6-1 was carried out to obtain a treated powder.

Example 6-6 The same surface modification as in Example 6-1 was performed using the silicone polymer-coated fine particle titanium dioxide of Example 1-6 to obtain a treated powder.

Example 6-7 The same surface modification as in Example 6-1 was performed using the silicone polymer-coated sericite of Example 1-7 to obtain a treated powder.

Example 6-8 Using the silicone polymer-coated fine particle silica gel of Example 1-8, the same surface modification as in Example 6-1 was carried out to obtain a treated powder.

Example 6-9 Using the silicone polymer-coated zinc white of Example 1-9, the same surface modification as in Example 6-1 was carried out to obtain a treated powder.

Example 7-1 Using the silicone polymer-coated fine particle silica gel of Example 1-1, the same operation as in Example 2-1 was performed with glycerol-α-monoallyl ether, and the surface was modified with a glycerin residue. The treated powder thus obtained was obtained.

Example 7-2 The same surface modification as in Example 7-1 was carried out using the silicone polymer-coated fine particles of titanium dioxide of Example 1-2 to obtain a treated powder.

Example 7-3 Using the silicone polymer-coated sericite of Example 1-3, the same surface modification as in Example 7-1 was carried out to obtain a treated powder.

Example 7-4 Using the silicone polymer-coated talc of Example 1-4, the same surface modification as in Example 7-1 was carried out to obtain a treated powder.

Example 7-5 Using the silicone polymer-coated titanium mica of Example 1-5, the same surface modification as in Example 7-1 was carried out to obtain a treated powder.

Example 7-6 Using the silicone polymer-coated fine particles of titanium dioxide of Example 1-6, the same surface modification as in Example 7-1 was carried out to obtain a treated powder.

Example 7-7 The same surface modification as in Example 7-1 was carried out using the silicone polymer-coated sericite of Example 1-7 to obtain a treated powder.

Example 7-8 Using the silicone polymer-coated fine particle silica gel of Example 1-8, the same surface modification as in Example 7-1 was carried out to obtain a treated powder.

Example 7-9 Using the silicone polymer-coated zinc white of Example 1-9, the same surface modification as in Example 7-1 was carried out to obtain a treated powder.

Example 8-1 100 g of the silicone polymer-coated fine particle silica gel of Example 1-1 was placed in a 3-liter eggplant-shaped flask, 300 g of water was added thereto, and high-speed stirring was conducted for 10 to 1 by a stirrer.
It was whipped for 5 minutes. Next, 6 g of chloromethylstyrene was added, and 10 g of chloroplatinic acid was further used as a catalyst.
After adding mg, the mixture was heated under reflux in a mantle heater at 80 to 90 ° C. for 5 hours. Then, 5 g of n-hexyldimethylamine was added, and the mixture was stirred and heated at 80 ° C. for 3 hours, filtered, washed with 2 liters of ethanol, degassed and dried, and treated powder surface-modified with a quaternary ammonium salt. Got the body

Example 8-2 Using the silicone polymer-coated fine particles of titanium dioxide of Example 1-2, the same surface modification as in Example 8-1 was performed to obtain a treated powder.

Example 8-3 Using the silicone polymer-coated sericite of Example 1-3, the same surface modification as in Example 8-1 was carried out to obtain a treated powder.

Example 8-4 Using the silicone polymer-coated talc of Example 1-4, the same surface modification as in Example 8-1 was carried out to obtain a treated powder.

Example 8-5 Using the silicone polymer-coated titanium mica of Example 1-5, the same surface modification as in Example 8-1 was carried out to obtain a treated powder.

Example 8-6 The same surface modification as in Example 8-1 was performed using the silicone polymer-coated fine particle titanium dioxide of Example 1-6 to obtain a treated powder.

Example 8-7 The same surface modification as in Example 8-1 was carried out using the silicone polymer-coated sericite of Example 1-7 to obtain a treated powder.

Example 8-8 Using the silicone polymer-coated fine particle silica gel of Example 1-8, the same surface modification as in Example 8-1 was carried out to obtain a treated powder.

Example 8-9 The same surface modification as in Example 8-1 was performed using the silicone polymer-coated zinc white of Example 1-9 to obtain a treated powder.

Example 9-1 Using the silicone polymer-coated fine particle silica gel of Example 1-1, the same operation as in Example 2-1 was carried out, and perfluorooctene represented by the following general formula (IIa) was used.

[0123]

[Chemical 9] To obtain a treated powder surface-modified with a perfluoroalkyl group.

Example 9-2 Using the silicone polymer-coated fine particles of titanium dioxide of Example 1-2, the same surface modification as in Example 9-1 was performed to obtain a treated powder.

Example 9-3 Using the silicone polymer-coated sericite of Example 1-3, the same surface modification as in Example 9-1 was performed to obtain a treated powder.

Example 9-4 Using the silicone polymer-coated talc of Example 1-4, the same surface modification as in Example 9-1 was carried out to obtain a treated powder.

Example 9-5 Using the silicone polymer-coated titanium mica of Example 1-5, the same surface modification as in Example 9-1 was carried out to obtain a treated powder.

Example 9-6 The same surface modification as in Example 9-1 was performed using the silicone polymer-coated fine particle titanium dioxide of Example 1-6 to obtain a treated powder.

Example 9-7 The same surface modification as in Example 9-1 was carried out using the silicone polymer-coated sericite of Example 1-7 to obtain a treated powder.

Example 9-8 Using the silicone polymer-coated fine particle silica gel of Example 1-8, the same surface modification as in Example 9-1 was carried out to obtain a treated powder.

Example 9-9 Using the silicone polymer-coated zinc white of Example 1-9, the same surface modification as in Example 9-1 was carried out to obtain a treated powder.

Example 10-1 Using the silicone polymer-coated fine particle silica gel of Example 1-1, the same operation as in Example 2-1 was carried out with allyl glycidyl ether, and the treated powder surface-modified with an epoxy group was used. Got

Example 10-2 The same surface modification as in Example 10-1 was performed using the silicone polymer-coated fine particle titanium dioxide of Example 1-2,
A treated powder was obtained.

Example 10-3 The same surface modification as in Example 10-1 was carried out using the silicone polymer-coated sericite of Example 1-3 to obtain a treated powder.

Example 10-4 Using the silicone polymer-coated talc of Example 1-4, the same surface modification as in Example 10-1 was carried out to obtain a treated powder.

Example 10-5 Using the silicone polymer-coated titanium mica of Example 1-5, the same surface modification as in Example 10-1 was carried out to obtain a treated powder.

Example 10-6 The same surface modification as in Example 10-1 was carried out using the silicone polymer-coated fine particle titanium dioxide of Example 1-6,
A treated powder was obtained.

Example 10-7 The same surface modification as in Example 10-1 was carried out using the silicone polymer-coated sericite of Example 1-7 to obtain a treated powder.

Example 10-8 Using the silicone polymer-coated fine particle silica gel of Example 1-8, the same surface modification as in Example 10-1 was carried out to obtain a treated powder.

Example 10-9 Using the silicone polymer-coated zinc white of Example 1-9, the same surface modification as in Example 10-1 was carried out to obtain a treated powder.

Example 11-1 Using the silicone polymer-coated fine particle silica gel of Example 1-1, the same operation as in Example 2-1 was performed, and the tetraol represented by the following general formula (IIb) was used.

[0142]

[Chemical 10] To obtain a treated powder surface-modified with an epoxy group.

Example 11-2 Using the silicone polymer-coated fine particle titanium dioxide of Example 1-2, the same surface modification as in Example 11-1 was carried out,
A treated powder was obtained.

Example 11-3 Using the silicone polymer-coated sericite of Example 1-3, the same surface modification as in Example 11-1 was carried out to obtain a treated powder.

Example 11-4 Using the silicone polymer-coated talc of Example 1-4, the same surface modification as in Example 11-1 was carried out to obtain a treated powder.

Example 11-5 Using the silicone polymer-coated titanium mica of Example 1-5, the same surface modification as in Example 11-1 was performed to obtain a treated powder.

Example 11-6 Using the silicone polymer-coated fine particle titanium dioxide of Example 1-6, the same surface modification as in Example 11-1 was carried out.
A treated powder was obtained.

Example 11-7 The same surface modification as in Example 11-1 was carried out using the silicone polymer-coated sericite of Example 1-7 to obtain a treated powder.

Example 11-8 Using the silicone polymer-coated fine particle silica gel of Example 1-8, the same surface modification as in Example 11-1 was carried out to obtain a treated powder.

Example 11-9 Using the silicone polymer-coated zinc white of Example 1-9, the same surface modification as in Example 11-1 was carried out to obtain a treated powder.

Example 12: Components of foundation by weight% (1) Treated powder of Example 6-3 10.0 (2) Titanium dioxide 13.0 (3) Colloidal kaolin 25.0 (4) Talc 34.7 (5) Red iron oxide 1.0 (6) Yellow iron oxide 2.5 (7) Black iron oxide 0.1 (8) Liquid paraffin 8.0 (9) Sorbitan sesquioleate 3.5 (10) Glycerin 2.0 (11) Ethylparaben 0.2 production method The above components (1) to (7) were mixed and pulverized with a pulverizer to an average particle size of 1 to 5 μm. This was transferred to a high speed blender, and the component (10) was added and mixed. Separately from this, the components (8), (9) and (11) were mixed and homogenized and added to the above mixture and further homogeneously mixed. This was treated with a crusher, passed through a sieve to adjust the particle size, and then compression-molded to obtain a cake-type foundation. The obtained foundation had good makeup lasting.

Example 13: Emulsion foundation compounding ingredients wt% (A) ion-exchanged water 43.5 sodium chondroitin sulfate 1.0 sodium lactate 0.5 1,3-butylene glycol 3.0 methylparaben suitable amount (B) dimethylpolysiloxane (20cs) 16.0 Decamethylcyclopentasiloxane 5.0 Silicone resin 1.0 Cetyl isooctanoate 1.0 Polyoxyalkylene-modified organopolysiloxane 4.0 (Modification rate 20%) Antioxidant Proper amount Perfume Proper amount (C ) Yellow iron oxide 1.0 Red iron oxide 0.45 Black iron oxide 0.2 Treated powder of Example 2-2 11.7 Treated powder of Example 5-3 11.65 Manufacturing method (B) is heated. After dissolution, powder of component (C) was added and dispersed. Ingredient (A) that has been dissolved and heated in advance
Was emulsified and cooled to room temperature to obtain an emulsified foundation.

Comparative Example 1 In the formulation of Example 13, Example 2-in component (C)
An emulsified foundation of Comparative Example 1 was obtained in the same manner as in Example 13 except that the untreated titanium dioxide was used instead of the treated powder of No. 2.

The material of Example 13 had better dispersibility of titanium dioxide than that of Comparative Example 1, and was finished nicely.
The sunscreen effect was high.

Example 14: Pressed powder blending component wt% (1) Treated powder of Example 9-4 30.0 (2) Treated powder of Example 7-3 65.8 (3) Iron oxide pigment 0 .1 (4) Squalane 2.0 (5) 2-Ethylhexyl palmitate 2.0 (6) Perfume 0.1 Production method The above components (1), (2) and (3) were mixed with a Henschel mixer, and mixed with this. A mixture obtained by heating and mixing the components (4) and (5) was sprayed, mixed and crushed, and then molded into a medium dish to obtain a pressed powder. The obtained pressed powder had a moisturizing effect and had a good makeup retention.

Example 15: UV protection stick compounding ingredients wt% (1) Treated powder of Example 2-2 20.0 (2) Treated powder of Example 5-4 10.0 (3) Example 5 -3 treated powder 11.0 (4) Iron oxide (red, yellow, black) 0.5 (5) Carnauba wax 1.0 (6) Solid paraffin 3.0 (7) Liquid paraffin 45.0 (8) Isopropyl myristate 8.0 (9) sorbitan sesquioleate 1.5 (10) Perfume Proper amount Production method The above components (7) and (8) are poured into a kettle and heated at 80 to 90 ° C.
The mixture was heated to and the components (5) and (6) were added and dissolved. Ingredients (1) to (4) were added thereto and dispersed uniformly, and after deaeration, ingredient (10) was added and gently stirred. This 8
It was poured into a container at 0 ° C. and cooled to room temperature to obtain an ultraviolet protection stick. The obtained stick had a high UV protection effect.

Example 16: Composition of lipstick wt% (1) Hydrocarbon wax 3.0 (2) Carnauba wax 1.0 (3) Glyceryl isostearate 40.0 (4) Liquid paraffin 45.8 (5) Treated powder of Example 7-2 4.0 (6) Mixed powder of iron oxide and sericite 6.0 (7) Perfume 0.2 Production method The components (1) to (4) were melted at 85 ° C. Components (5) and (6) were added to the mixture with stirring. Then, the component (7) was added under stirring. The resulting mixture was charged into a container. The lipstick obtained had excellent dispersibility.

Example 17: Components for sunscreen cream wt% (A) Decamethylcyclopentasiloxane 42.0 Polyethylene glycol 5.0 Dispersant Appropriate amount (B) Cetyl alcohol 5.0 Vaseline 10.0 Dimethylpolysiloxane (10cs) / 25 ° C) 5.0 Methylphenylpolysiloxane (20cs / 25 ° C) 5.0 Microcrystalline wax 5.0 Glyceryl monostearate 3.0 Polyoxyethylene sorbitan monostearate 3.0 Perfume proper amount Preservative proper amount antioxidant Agent Appropriate amount (C) Treated powder of Example 2-2 5.0 Coloring pigment Appropriate amount After the manufacturing method (A) phase was melted by heating, the (C) phase was added and uniformly dispersed with a homomixer. What melt | dissolved the (B) phase by heating was added to it, and it stirred well, and after homogenizing with a homomixer, stirring and cooling obtained the sunscreen cream. The obtained cream had a high sunscreen effect.

Example 18: Ingredients for body powder Wt% (A) Talc 50.0 Treated powder of Example 8-4 39.0 Pearling agent 1.0 Coloring pigment Appropriate amount (B) Zinc white 3.0 (C ) Magnesium stearate 4.0 Liquid paraffin 1.0 Bactericide Proper amount (D) Perfume Proper amount Mix the production method (A) with a blender. (B) is added to this and mixed well, then (C) is added and after the color is adjusted, the fragrance (D) is sprayed and uniformly mixed. This was crushed with a crusher and passed through a sieve to obtain a body powder. The obtained body powder had a high deodorizing effect.

Example 19: Paint 20 g of the treated powder obtained in Example 4-2 and 18 g of an acrylic resin solution (Mn48,200, Mw / Mn2.56) were kneaded together with 70 g of glass beads for 20 minutes on a paint shaker to form a paint. Got The obtained paint had high light resistance.

Example 20: Container A white polystyrene wide-mouth bottle was injection molded by mixing 2% by weight of the treated powder obtained in Example 4-3 with polyethylene.

Comparative Example 2 As a comparative example, a white polystyrene wide-mouth bottle was injection-molded without mixing the treated powder.

Pieces each having a size of 4 cm × 4 cm were cut out from the wide-mouth bottles of Example 20 and Comparative Example 2, and the ultraviolet absorption spectrum (diffuse reflection method) was measured. The pieces obtained in Example 20 were found to be the same. A high UV absorption effect was observed.

[0164]

As described in detail above, in the present invention, in the method for producing a treated powder, the powder coated with the silicone compound having a Si--H group is treated with a compound capable of reacting with the Si--H group. Since it is configured to use substantially only water as the reaction solvent when adding, it is possible to reduce the manufacturing cost and reduce the burden on the environment such as drainage. Safe and stable treated powder There is an effect that a method for manufacturing a body can be provided. In addition, the manufacturing efficiency of the product using the treated powder obtained by the above manufacturing method is improved, the manufacturing cost is reduced, the stability and safety of the product quality are ensured, and the economical and work load in terms of environmental measures. Can be reduced.

Continuation of front page (51) Int.Cl. ⁷ identification code FI C09C 3/12 C09C 3/12 (56) Reference JP-A-1-110540 (JP, A) JP-A-5-85715 (JP, A) Japanese Patent Publication 1-54380 (JP, B2) (58) Fields investigated (Int.Cl. ⁷ , DB name) C08L 83/06 A61K 7/02 A61K 7/42 C08J 7/16 C08K 9/06 C09C 3 / 12

Claims (24)

(57) [Claims] 1. Production of a treated powder, which comprises coating a powder with a silicone compound having a Si—H group and then adding a compound capable of reacting with the Si—H group to the Si—H group portion of the silicone compound. In the method, the addition is carried out using substantially only water as a reaction solvent. 2. The silicone compound having a Si—H group has the general formula (I): [In the formula, R ¹ , R ² and R ³ are each independently a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms and substitutable with at least one halogen atom (provided that R ¹ ,
R ² and R ³ are not hydrogen atoms at the same time); R
⁴ , R ⁵ and R ⁶ are each independently a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which can be substituted with at least one halogen atom; a is 0 or an integer of 1 or more, b is 0 or an integer of 1 or more, c is 0 or 2 (provided that 3 ≦ a + b + c ≦ 10000); and this compound is assumed to contain at least one Si—H group moiety]. The method for producing a treated powder according to claim 1, which is a silicone compound. 3. The method for producing a treated powder according to claim 2, wherein c = 0 in the general formula (I). 4. The method for producing treated powder according to claim 2, wherein c = 2 in the general formula (I). 5. The method for producing treated powder according to claim 1, wherein the silicone compound is methylhydrogenpolysiloxane (molecular weight 6000). 6. The silicone compound is 1, 3, 5, 7
-The method for producing a treated powder according to any one of claims 1, 2 and 4, which is tetramethylcyclotetrasiloxane. 7. The powder is one of an organic pigment, an inorganic pigment, a metal oxide, a metal hydroxide, a mica, a pearl luster, a metal, a magnetic powder, a silicate mineral or a porous substance, or The method for producing treated powder according to any one of claims 1 to 6, which is a combination of two or more kinds. 8. The powder is silica gel, titanium dioxide,
Sericite, talc, mica titanium or zinc white,
A method for producing the treated powder according to any one of claims 1 to 7. 9. The compound capable of reacting with the Si—H group is an unsaturated compound having at least one carbon-carbon double bond or triple bond and capable of reacting with the Si—H group, A method for producing the treated powder according to any one of claims 1 to 8. 10. The compound capable of reacting with the Si—H group has the general formula (II): {In the formula, R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are independently of each other a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, an acyloxy group, an alkoxy group, an amino group, a nitro group, a carboxyl group, a sulfo group, or a carbon atom. A substituted or unsubstituted hydrocarbon group of the number 1 to 30 [eg, aliphatic group (eg, alkyl group, alkenyl group, alkynyl group), aromatic group (eg, phenyl group, naphthyl group), heterocyclic group (eg, hetero atom) A compound containing at least one nitrogen atom, oxygen atom or sulfur atom), an alicyclic group (eg cycloalkyl group, cycloalkenyl group, cycloalkynyl group), spiro compound residue or terpene compound residue] ;
Alternatively, R ¹¹ and R ¹³ form a carbon-carbon bond, and -C =
Can be combined with C- to form -C≡C-;
Alternatively, R ¹² and R ¹⁴ form a carbon-carbon bond, and -C =
Can form an alicyclic group together with C-}
The method for producing treated powder according to any one of claims 1 to 9, which is a compound represented by. 11. The treated powder according to any one of claims 1 to 10, wherein the compound capable of reacting with the Si—H group is 2-hydroxy-3-allyl-4methoxybenzophenone. Production method. 12. The treated powder according to claim 1, wherein the compound capable of reacting with the Si—H group is allyl-3,4,5-trimethoxycinnamate. Manufacturing method. 13. The compound capable of reacting with the Si—H group is 2- (2-hydroxy-3-allyl-methylphenyl) benzotriazole, 1 to 1.
0. The method for producing the treated powder according to any one of 0. 14. The treated powder according to claim 1, wherein the compound capable of reacting with the Si—H group is 4-allyloxy-4′-t-butylbenzoylmethane. Manufacturing method. 15. The method for producing a treated powder according to claim 1, wherein the compound capable of reacting with the Si—H group is tetradecene. 16. The method for producing a treated powder according to claim 1, wherein the compound capable of reacting with the Si—H group is glycerol-α-monoallyl ether. 17. The compound capable of reacting with the Si—H group is chloromethylstyrene.
Item 10. The method for producing a treated powder according to any one of items 10. 18. The compound capable of reacting with the Si—H group has the general formula (IIa): A perfluorooctene represented by the formula 1.
0. The method for producing the treated powder according to any one of 0. 19. The method for producing a treated powder according to claim 1, wherein the compound capable of reacting with the Si—H group is allyl glycidyl ether. 20. The compound capable of reacting with the Si—H group is represented by the general formula (IIb): The method for producing a treated powder according to claim 1, which is tetraol represented by: 21. A cosmetic composition is produced by a conventional method using the treated powder obtained by the production method according to claim 1 as one component of a raw material. A method for producing a cosmetic composition. 22. The cosmetic composition comprises a cake type foundation, an emulsified foundation, a pressed powder,
The method for producing a cosmetic composition according to claim 21, which is one of an ultraviolet protection stick, lipstick, sunscreen cream, and body powder. 23. A coating composition is produced by an ordinary method using the treated powder obtained by the production method according to claim 1 as one component of a raw material. And a method for producing a coating composition. 24. A synthetic resin composition is injection-molded by an ordinary method using the treated powder obtained by the production method according to claim 1 as one component of a raw material. And a method for manufacturing a resin molded product.