JPH09104833A - Pigment subjected to hydrophilic treatment and composition containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject pigment having sufficient hydrophilicity, excellent in dispersibility, and not causing skin irritation, etc., by introducing hydrophilic organic groups to the surface of a pigment by a surface-treating method using a hydrophilic silane compound, etc. SOLUTION: This hydrophilic pigment is produced by treating the surface of a pigment with a hydrophilic silane compound or a silane coupling agent to introduce hydrophilic organic groups to the surface of the pigment. The hydrophilic silane compound is preferably a silane compound of the formula: (R<1> O)a R<2> b SiR<3> O(C2 H4 O)p (C3 H6 O)q R4 (R<1> is a 1-10C alkyl; R<2> is a 1-10C alkyl, phenyl; R<3> is a 2-5C divalent hydrocarbon group; R<4> is H, a 1-10C alkyl, etc.; (a) is an integer of 1-3; (b) is an integer of 0-2; a+b=3; (p) is an integer of 2-200; (q) is an integer of 0-200; p+q= an integer of 3-200; p/q>=1).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a novel hydrophilized pigment having a hydrophilic organic group introduced on the surface of the pigment, and a composition containing the pigment.

[0002]

2. Description of the Related Art Untreated pigments may cause inconveniences such as agglomeration based on the charge and polarity of the pigment surface, or a decrease in the hydrophilicity due to the interfacial tension of the pigment. For the purpose of eliminating these inconveniences and improving the pigment dispersibility and dispersion stability, surface treatment has been conventionally proposed in which the surface of the pigment is treated with various modifiers. The treatment agent or treatment method used for the surface treatment of this pigment varies depending on the purpose, and is selected in consideration of the surface properties of the pigment to be treated and the characteristics with respect to the dispersion medium, for example, a lipophilic treatment with an oil agent or a metal soap,
Known are hydrophilic treatment with a surfactant and a water-soluble polymer, water-repellent treatment with silicone oil and the like.

[0003]

However, regarding the hydrophilic treatment of the pigment, it cannot be said that the conventional hydrophilic treatment with a surfactant or a water-soluble polymer is sufficient. In the compounded composition, the pigment and the treating agent are dissociated in the system, the pigment is aggregated to cause color unevenness, the appearance color and the coating color are different from each other, and the redispersibility is deteriorated with time. In some cases, it deteriorated and the usability was significantly impaired. Furthermore, depending on the type of surfactant used, skin irritation may occur, which may be a problem particularly when used in cosmetics. In view of the above circumstances, the present invention has an object to provide a hydrophilic treatment pigment having sufficient hydrophilicity, excellent dispersibility, and causing no skin irritation, and a composition containing the same. .

[0004]

Means for Solving the Problems As a result of intensive studies on the hydrophilization of pigments, the present inventors have found that a hydrophilically treated pigment surface-treated with a hydrophilic silane compound or a silane coupling agent is excellent in dispersion. It was found that the composition and the dispersion stability of the composition are excellent, and the composition containing the composition is excellent in usability, and thus the present invention has been completed. That is, the present invention is a hydrophilized pigment obtained by introducing a hydrophilic organic group using a hydrophilic silane compound or a silane coupling agent, and a composition containing the pigment.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail.
First, a hydrophilized pigment in which a hydrophilic organic group is introduced by using a hydrophilic silane compound will be described. The hydrophilic silane compound used in the present invention is a silane compound having a hydrophilic organic group. As the silane compound having a hydrophilic organic group, a hydrophilic silane compound having a polyoxyethylene chain is preferably used. In this case, the kind of the hydrophilic silane compound is not particularly limited as long as it has a polyoxyethylene chain, but among them, the silane compound represented by the following general formula (1) is preferable. (R ¹ O) _a R ² _b SiR ³ O (C ₂ H ₄ O) _p (C ₃ H ₆ O) _q R ⁴ (1) (In the formula, R ¹ is an alkyl group having 1 to 10 carbon atoms; ² is an alkyl group having 1 to 10 carbon atoms or a phenyl group, R ³ is a divalent hydrocarbon group having 2 to 5 carbon atoms, R ⁴ is hydrogen, and 1 to 10 carbon atoms.
Or an —R ³ SiR ² _b (OR ¹ ) _a group. In addition, a is an integer of 1 to 3, b is an integer of 0 to 2, and a +
b is 3. p is an integer of 2 to 200, q is 0 to 200
, And p + q is an integer of 3 to 200. Moreover, p / q is 1 or more. )

To give a concrete example, for example, (CH ₃ O) ₃
SiC ₃ H ₆ O (C ₂ H ₄ O) ₁₀ H, (CH ₃ O) ₃ SiC ₃ H ₆ O
(C ₂ H ₄ O) ₁₀ CH ₃ , (CH ₃ O) ₃ SiC ₃ H ₆ O (C ₂ H
₄ O) ₁₀ C ₃ H ₆ Si (OCH ₃ ) ₃ , (CH ₃ CH ₂ O) ₃ SiC _{3
H 6 O (C 2 H 4} O) 20 (C 3 H 6 O) 10 CH 3, (CH 3 O) 3 Si
_{C 3 H 6 O (C 2} H 4 O) 30 C 2 H 5, (CH 3) (CH 3 O) 2 Si
_{C 3 H 6 O (C 2} H 4 O) 5 C 3 H 7, (CH 3 O) 3 SiC 4 H 8 O
_{(C 2 H 4 O) 10} C 4 H 9, (C 4 H 9 O) (CH 3) 2 SiC 5 H 10
_{O (C 2 H 4 O)} 20 CH 3 and the like.

In order to make the pigment hydrophilic by using the above-mentioned hydrophilic silane compound having a polyoxyethylene chain, the surface of the pigment is directly treated with the hydrophilic silane compound for hydrophilic treatment. For this treatment, for example, the pigment is dispersed in water, alcohol or a mixture thereof, and a hydrophilic silane compound similarly dissolved in water, alcohol or a mixture thereof is added to the dispersion, and the mixture is stirred or ball-milled. After that, a wet method of removing water, drying, heat treatment, and crushing,
A method such as a dry method in which a hydrophilic silane compound is sprayed on the pigment, dried and heat-treated is used. Conventionally known methods can be adopted for these processing operations themselves.

Next, the hydrophilized pigment in which a hydrophilic organic group is introduced by using a silane coupling agent will be described.
To introduce a hydrophilic organic group into a pigment using a silane coupling agent, first treat the pigment with a silane coupling agent, and then react or polymerize the compound having a hydrophilic organic group with the silane coupling agent. By.
Specifically, for example, after introducing an epoxide group on the pigment surface with an epoxide group-containing silane coupling agent, a method of reacting a water-soluble compound having a hydroxyl group or an amino group in the presence of a catalyst such as boron trifluoride, After introducing a radical polymerizable group on the pigment surface with a radical polymerizable group-containing silane coupling agent, a method of polymerizing an ionic and / or nonionic water-soluble radical monomer to introduce a hydrophilic chain, an amino group A method of introducing a polyoxyethylene chain by adding ethylene oxide after introducing an amino group on the pigment surface with a silane coupling agent having, similarly reacting a glycidyl compound having a polyoxyethylene chain under a suitable catalyst. There is a method to introduce it, but
The present invention is not limited to these.

The pigment in the present invention is, for example, titanium oxide, zinc oxide, cerium oxide, zirconium oxide, black iron oxide, yellow iron oxide, red iron oxide, titanium monoxide, chromium oxide, ultramarine blue, dark blue, talc, kaolin, mica, Magnesium carbonate, calcium carbonate, aluminum silicate, magnesium silicate, anhydrous silicic acid, barium sulfate, titanium mica, iron oxide mica, iron iron mica titanium, tar pigments, natural pigments, nylon powder, polyethylene powder, polytetrafluoroethylene powder , Wool powder, silk powder, crystalline cellulose and the like.

The amount of the hydrophilizing agent with respect to the pigment varies depending on the type of the pigment and the hydrophilizing agent used and the hydrophilizing method, and is not particularly limited, but preferably 0.1 of the pigment.
-20% by weight (hereinafter referred to simply as "%"), and more preferably 0.3-10%. The hydrophilically treated pigment of the present invention has a hydrophilic organic group firmly bonded to the surface of the pigment, and has excellent dispersibility and dispersion stability. Further, those having a polyoxyethylene chain as the hydrophilic organic group have particularly excellent performance.

The hydrophilized pigment obtained as described above is excellent in dispersibility and dispersion stability in an aqueous system. for that reason,
It can be applied to various compositions containing a pigment, such as cosmetics, external preparations for skin, paints, inks and the like. When the hydrophilically treated pigment of the present invention is added to the composition, the amount thereof is not particularly limited, but is preferably 0.1 to 99%, more preferably 0.1 to 95%. As cosmetics, foundation, cheek color, eye shadow,
Examples include lipstick, mascara, eyeliner, nail enamel, lotion, emulsion, cream, pack and beauty essence. The composition of the present invention includes an oil agent, a solvent, water, a surfactant, a film forming agent, a plasticizer, a humectant, an emollient agent, a water-soluble polymer,
Antiseptic, UV absorber, dye, antioxidant, beauty ingredient,
Fragrances and the like can be appropriately added within a range that does not impair the effects of the present invention. Further, the hydrophilized pigment of the present invention may be used in combination with an untreated pigment.

[0012]

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited thereto. Production Example 1 100 g of titanium oxide (CR-50, manufactured by Ishihara Sangyo Co., Ltd.) was dispersed in 40 g of methanol to obtain a uniform slurry. To this slurry was added 10 g of a 30% aqueous solution of a hydrophilic silane compound having a polyoxyethylene chain represented by the following formula, and the mixture was treated with a ball mill for 5 minutes. The treated slurry was dried under reduced pressure and then heat-treated at 100 ° C. for 1 hour.
This was washed with ethanol, dried and then pulverized to obtain titanium oxide whose surface was hydrophilized. _{(CH 3 O) 3 SiC 3} H 6 O (C 2 H 4 O) n CH 3 [ where a n = 30 to 34. ]

Production Example 2 100 g of talc (high filler made by Matsumura Sangyo Co., Ltd.) was placed in a table crusher, and 2 g of a hydrophilic silane compound having a polyoxyethylene chain represented by the following formula was dissolved in 8 g of purified water and spray-added. While mixing for 10 minutes. This was dried under reduced pressure, then heat-treated at 100 ° C. for 1 hour, washed with ethanol, dried and pulverized to obtain talc having a surface hydrophilized. _{(CH 3 O) 3 SiC 3} H 6 O (C 2 H 4 O) r (C 3 H 6 O) t C
H ₃ [wherein r / t = 2.5 to 3.5, r + t = 25 to 35]
It is. ]

Production Example 3 Bengal (Bengala cloisonne, manufactured by Morishita Bengal Kogyo Co., Ltd.) 20
g was dispersed in 10 g of methanol, and an aqueous solution prepared by dissolving 0.6 g of a hydrophilic silane compound having a polyoxyethylene chain represented by the following formula in 5 g of purified water was added to obtain a uniform slurry. This slurry was mixed in a mortar, dried and then heat-treated at 100 ° C. This was washed with ethanol, dried and pulverized to obtain red iron oxide whose surface was hydrophilized. _{(CH 3 O) 3 SiC 3} H 6 O (C 2 H 4 O) m CH 3 [ where a m = 18 to 22. ]

Production Example 4 Black iron oxide (Tarox Black, manufactured by Titanium Industry Co., Ltd.) 20
g was dispersed in 10 g of methanol, and the hydrophilic silane compound having a polyoxyethylene chain used in Production Example 3 0.6
An aqueous solution prepared by dissolving g in 5 g of purified water was added to form a uniform slurry. The slurry is mixed in a mortar and dried to 100
Heat treatment was performed at ℃. This was washed with ethanol, dried and pulverized to obtain black iron oxide whose surface was hydrophilized.

Production Example 5 Yellow iron oxide (Tarox Yellow, manufactured by Titanium Industry Co., Ltd.) 20
g was dispersed in 10 g of methanol, and the hydrophilic silane compound having a polyoxyethylene chain used in Production Example 3 0.6
An aqueous solution prepared by dissolving g in 5 g of purified water was added to form a uniform slurry. The slurry is mixed in a mortar and dried to 100
Heat treatment was performed at ℃. This was washed with ethanol, dried and then pulverized to obtain yellow iron oxide whose surface was hydrophilized.

Production Example 6 Mica (Yamaguchi Mica Industry Co., Ltd., Mica Y-3000) 10
0 g was placed in a table grinder, and 2 g of the hydrophilic silane compound having a polyoxyethylene chain used in Production Example 2 dissolved in 8 g of purified water was sprayed and mixed for 10 minutes. This was dried under reduced pressure, then heat-treated at 100 ° C. for 1 hour, washed with ethanol, dried and pulverized to obtain a mica whose surface was hydrophilized.

Production Example 7 50 g of zinc oxide (manufactured by Sakai Chemical Co., Ltd., fine zinc white) was dispersed in 80 g of ethanol, and an aqueous solution of a silane coupling agent having an amino group represented by the following formula (silane coupling agent 1
g, 5 g of purified water) to make a uniform slurry. This slurry is mixed in a mortar for 10 minutes, dried and then mixed at 100 ° C. for 3 minutes.
It was heat-treated for 0 minutes and crushed. (CH ₃ O) ₃ Si (CH ₂ ) ₃ NH ₂ 20 g of the obtained powder was dispersed in 50 ml of diethyl ether, and 20 g of a 20% diethyl ether solution of a hydrophilizing agent represented by the following formula and trifluoride were added to the dispersion. An addition reaction was carried out by adding 5 ml of boron diethyl ether complex. After completion of the reaction, the solvent was distilled off to obtain zinc oxide whose surface was hydrophilized.

[0019]

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Production Example 8 100 g of titanium oxide (A-100 manufactured by Ishihara Sangyo Co., Ltd.) was dispersed in 40 g of methanol to obtain a uniform slurry. 10 g of a 30% aqueous solution of the hydrophilic silane compound having a polyoxyethylene chain used in Production Example 1 was added, and the mixture was treated with a ball mill for 5 minutes. The treated slurry was dried under reduced pressure and heat-treated at 100 ° C. for 1 hour. This was washed with ethanol, dried and then pulverized to obtain titanium oxide whose surface was hydrophilized.

Production Example 9 Yellow No. 4 Aluminum Lake (manufactured by Sanei Chemical Industry Co., Ltd.) 50
Into a mortar, 5 g of a 30% methanol solution of the hydrophilic silane compound having a polyoxyethylene chain used in Production Example 2 was added and mixed for 20 minutes. This was dried under reduced pressure and then heat-treated at 100 ° C. for 1 hour. This was washed with ethanol, dried and then pulverized to obtain a yellow No. 4 aluminum lake whose surface was hydrophilized.

Production Example 10 40 g of nylon powder (manufactured by Toray Industries, Inc.) was placed in a mortar, and 4 g of a 20% methanol solution of the hydrophilic silane compound having a polyoxyethylene chain used in Production Example 3 was added.
Mix for 0 minutes. After drying it under reduced pressure, it is dried at 100 ° C for 1
Heat treatment was performed for an hour. This was washed with ethanol, dried and then pulverized to obtain a nylon powder whose surface was hydrophilized.

Production Example 11 100 g of titanium oxide (CR-50, manufactured by Ishihara Sangyo Co., Ltd.) was placed in a table grinder, and 3 g of a hydrophilic silane compound having a polyoxyethylene chain represented by the following formula was dissolved in 7 g of ethanol and sprayed. Mix for 10 minutes with addition. This was dried under reduced pressure and then heat-treated at 100 ° C. for 1 hour. This was washed with ethanol, dried and then pulverized to obtain titanium oxide whose surface was hydrophilized. _{(CH 3 O) 3 SiC 3} H 6 O (C 2 H 4 O) 20 C 3 H 6 Si (OC
H ₃ ) ₃

Preparation Comparative Example 1 The same procedure as in Preparation Example 1 was carried out using 10 g of a 30% aqueous solution of polyoxyethylene lauryl ether phosphoric acid instead of the hydrophilic silane compound to obtain a hydrophilized titanium oxide.

Test Example 1 5 g of the hydrophilized titanium oxide of Production Example 1 and Production Comparative Example 1 and 5 g of untreated titanium oxide were separately added to an aqueous solution of which pH was adjusted to 4 to 8 by adding 5 g of a buffer solution to 90 g of purified water. Then, it was dispersed well, and then allowed to stand to observe each dispersed state. The result is x if it sediments within 5 minutes,
Those that settled within 15 hours were evaluated as Δ, and those that did not settle for 15 hours were evaluated as ◯.

[0026]

[Table 1]

As is clear from the evaluation results, untreated titanium oxide caused sedimentation at a pH of 6.5 or less. Further, the effect was not improved even in the conventional hydrophilic treatment with a surfactant. On the other hand, the hydrophilic silane compound-treated titanium oxide of the present invention does not aggregate in a wide pH range,
It had excellent dispersibility and dispersion stability.

Test Example 2 An appropriate amount of the hydrophilized yellow No. 4 aluminum lake and the untreated Yellow No. 4 aluminum lake of Production Example 9 were separately added to purified water and stirred to observe the effect of the hydrophilizing treatment. The hydrophilically treated yellow No. 4 aluminum lake according to the present invention was easily wet with water and uniformly dispersed by light stirring. On the other hand, the untreated yellow No. 4 aluminum lake did not wet the water, remained floating on the surface of the water, and did not disperse. Similarly, when the hydrophilized nylon powder of Production Example 10 and an untreated nylon powder were tested, the dispersibility of the hydrophilized nylon powder of the present invention in water was excellent.

Example 1 and Comparative Examples 1 to 3 Pack Cosmetics Pack cosmetics having the following components and proportions (% by weight) were produced, and the dispersibility of pigments, the dispersion stability and the feeling of use were evaluated.

[0030]

[Table 2]

(Manufacturing Method) A: Components 1 to 3 are mixed and dissolved by heating, and then components 4 to 8 are added.
Was mixed and dissolved and added. B: Ingredients 9 to 13 were mixed and subjected to triple roll treatment. C: B was added to and mixed with A, and further components 14 to 15 were added and uniformly mixed to obtain a pack cosmetic.

In Example 1 relating to the product of the present invention, the state of dispersion of the pigment was good, and the feeling of use had a smooth elongation. Furthermore, since the dispersion effect is durable, the stability over time was excellent. On the other hand, in Comparative Example 1, the pigment aggregated and was not uniformly dispersed. As a result, a rough feeling was produced when applied to the skin, and the whiteness of the coating film was non-uniform, and the pigment became white and lumpy, resulting in a very bad usability. Further, it was inferior such as the pigment settling out with time. In Comparative Example 2, the dispersion state was slightly better than that of Comparative Example 1, but the effect was low and not satisfactory. In Comparative Example 3 as well, the surfactant was dissociated with time, so that it had only the same effect as Comparative Example 2. Furthermore, in Comparative Examples 2 and 3, since the phosphoric acid type surfactant was used, the product of the present invention was superior in safety.

Example 2 and Comparative Example 4 Foundation (two-layer type) A foundation (two-layer type) having the components and proportions (% by weight) shown below was produced, and the dispersibility, dispersion stability and usability of the pigment were evaluated. did.

[0034]

[Table 3]

(Manufacturing Method) A: Components 1 to 10 were mixed, and component 11 was added to the mixture to perform a three-roll treatment. B: Components 12 to 15 were added to A and mixed uniformly to obtain a foundation.

In Example 2 relating to the product of the present invention, the state of dispersion of the pigment was good, and the feeling of use had a smooth elongation. Further, the pigment was easily redispersed by shaking during use, and was excellent in stability over time. Furthermore, since there is no aggregation of the pigment, there is no hue difference between the appearance color and the coating color, and it has excellent usability. On the other hand, in Comparative Example 4, the pigment tended to aggregate, and as a result, a rough feeling was produced and the usability was poor. Furthermore, the tendency of the pigments to aggregate with time progresses, making it difficult for the pigments to re-disperse even when shaking, and because the pigments that have aggregated due to external forces when applied to the skin are dispersed, there is a significant hue difference between the appearance color and the coating color. It was inferior and so on.

Example 3 Mascara (ingredient) (%) 1. Stearic acid 2.0 2. Carnauba Barrow 2.0 3. White beeswax 7.0 4. Polyoxyethylene monooleate 0.8 sorbitan (20 EO) 5. Sorbitan sesquioleate 0.4 6. Triethanolamine 0.5 7. Sucrose fatty acid ester 1.5 8. Treated black iron oxide (Production Example 4) 6.0 9. Treated mica (Production Example 6) 5.0 10.1, 3-butylene glycol 2.5 11. Preservative appropriate amount 12. Polyacrylic acid ethyl ester emulsion 50.0 13. Purified water balance

(Production Method) A: Components 1 to 7 were dissolved by heating. B: Three rolls of components 8 to 10 were processed. C: Components 11 to 13 were added to B and heated. D: C was added to A to emulsify, and this was cooled to obtain mascara. Example 3 was a mascara in which the dispersed state of the pigment was good, the gloss was good, and the feeling of use was smooth.

Example 4 Lotion (Component) (%) 1. Kaolin 0.5 2. Treated zinc oxide (Production Example 7) 0.3 3. Purified water 10.0 4. l-menthol 0.01 5. Alcohol 18.0 6. Purified water remaining amount (manufacturing method) A: Components 1 to 3 were mixed and subjected to colloid mill treatment. B: Components 4 to 6 were mixed and dissolved, and A was added to this to obtain a lotion. Example 4 was a lotion in which the powder was easily dispersed uniformly by shaking during use, and which was excellent in usability with no roughness when applied to the skin.

Example 5 Regular dry water-soluble lacquer resin paint (component) (%) Normal dry type water-soluble acrylic resin (nonvolatile solid content 41.5%) 58.4 2. Butyl cellosolve 1.0 3. Butyl carbitol 2.5 4. Water 17.3 5. Treated titanium oxide (Production Example 11) 19.8 6. Clay Mineral 1.0 (Production Method) Components 1 to 6 were mixed and dispersed by a sand grinder to obtain a normally dry water-soluble lacquer resin coating material. This lacquer had good pigment dispersion, did not cause precipitation of the pigment, and had excellent stability over time.

Example 6 Water-based ink for writing instruments (component) (%) 1. Ethylene glycol 15.0 2. Treated black iron oxide (Production Example 4) 12.0 3. John Cryl J61j (manufactured by Johnson Polymer Co., Ltd.) 2.5 4. Purified water 70.5 (Production method) After dispersing the above components with a bead mill, a black aqueous ink for writing instruments was obtained. This ink was filled into a commercially available fiber-converged pen tip batting type writing instrument and evaluated. As a result, it was found to have a smooth writing feel without blur and excellent stability over time.

[0042]

As described above in detail, the hydrophilized pigment of the present invention has excellent dispersibility and dispersion stability.
Therefore, the hydrophilized pigment of the present invention is useful as a pigment component of various compositions, and a composition containing the hydrophilized pigment is excellent in usability and stability over time.
Further, it is suitable for cosmetics because it is safe without skin irritation.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Office reference number FI Technical display location A61K 7/48 A61K 7/48 C08K 3/00 KAA C08K 3/00 KAA C08L 101/00 C08L 101 / 00 C09D 4/02 C09D 4/02 (72) Inventor Koji Sakuta 1-10 Hitomi, Matsuida-cho, Usui-gun, Gunma Prefecture Shin-Etsu Chemical Co., Ltd. Silicone Electronic Materials Research Laboratory (72) Inventor Shoji Ichinohe Gunma Prefecture 1-10 Hitomi, Matsuida-cho, Usui-gun Shin-Etsu Chemical Co., Ltd. Silicone Electronic Materials Research Laboratory

Claims (4)

[Claims] 1. A hydrophilized pigment obtained by introducing a hydrophilic organic group using a hydrophilic silane compound or a silane coupling agent. 2. The hydrophilically treated pigment according to claim 1, wherein the hydrophilic silane compound is a hydrophilic silane compound having a polyoxyethylene chain. 3. The hydrophilically treated pigment according to claim 2, wherein the hydrophilic silane compound having a polyoxyethylene chain is a silane compound represented by the following general formula (1). (R ¹ O) _a R ² _b SiR ³ O (C ₂ H ₄ O) _p (C ₃ H ₆ O) _q R ⁴ (1) (In the formula, R ¹ is an alkyl group having 1 to 10 carbon atoms; ² is an alkyl group having 1 to 10 carbon atoms or a phenyl group, R ³ is a divalent hydrocarbon group having 2 to 5 carbon atoms, R ⁴ is hydrogen, and 1 to 10 carbon atoms.
Or an —R ³ SiR ² _b (OR ¹ ) _a group.
In addition, a is an integer of 1 to 3, b is an integer of 0 to 2,
+ B is 3. p is an integer of 2 to 200, q is 0 to 20
0 is an integer, and p + q is an integer of 3 to 200. Moreover, p / q is 1 or more. ) 4. A composition comprising the hydrophilization-treated pigment according to claim 1, claim 2 or claim 3.