WO2024127905A1 - Method for producing organopolysiloxane emulsion composition - Google Patents

Abstract

The present invention is a method for producing an organopolysiloxane emulsion composition characterized in that an organopolysiloxane generated by (I) emulsifying a mixture containing (A) an organopolysiloxane represented by general formula (1) and having an octamethylcyclotetrasiloxane (D4) content of 3,000 ppm or less, (B) an organoalkoxysilane represented by general formula (2), (C) a nonionic surfactant, and (D-1) water to prepare a first emulsion composition, (II) adding (D-2) water to the composition, and then conducting emulsion polymerization in the presence of (E) an organic base catalyst at less than 40°C has a viscosity at 25°C of 300,000 mPa∙s or more, a D4 content of 3,000 ppm or less, and an average particle size of emulsion particles in the composition of 1 μm or less. Provided thereby is a method for producing a high-viscosity organopolysiloxane emulsion composition in which by-production of D4 is suppressed, the particle size is small, and the stability over time is good.

Description

Method for producing organopolysiloxane emulsion composition

The present invention relates to a method for producing a high-viscosity organopolysiloxane emulsion composition having a branched structure for use in products such as cosmetics, personal care compositions, home care compositions, release agents, slip agents, coating agents, fiber treatment agents, and resin modifiers.

There is a demand for high-viscosity organopolysiloxanes used in products such as cosmetics, personal care compositions, home care compositions, release agents, slip agents, coating agents, fiber treatment agents, and resin modifiers to be made into emulsions with small particle size and good stability over time. However, when high-viscosity organopolysiloxanes with a branched structure are directly emulsified, the particle size of the emulsion particles is limited to a few microns, and it is difficult to obtain particles smaller than this, and the stability of the resulting emulsions over time is poor. Therefore, various methods for producing emulsions of high-viscosity organopolysiloxanes with a branched structure by emulsion polymerization have been investigated in order to obtain emulsion particles with small particle size and good stability over time.

For example, a method is known in which cyclic siloxane oligomers and trialkoxysilanes are emulsified and then subjected to emulsion polymerization using strong acid or strong alkali. Using these methods, it is possible to obtain emulsions with emulsion particles having a particle size of 300 nm or less.

In recent years, however, there has been a demand for products with reduced octamethylcyclotetrasiloxane (D4) content. However, it is known that the organopolysiloxane contained in the emulsion obtained by the above method contains 40,000 ppm or more of octamethylcyclotetrasiloxane, and methods for reducing this content are being investigated.

For example, a method is known in which an organopolysiloxane having a viscosity of 3,000 to 100,000 mm ² /s at 25° C., an octamethylcyclotetrasiloxane content of 1,000 ppm or less, and whose molecular chain ends are blocked with silanol groups, is emulsified, and then emulsion polymerization is carried out in the presence of an acid catalyst at a temperature of less than 40° C. (Patent Document 1), and it is said that by using these techniques, an emulsion can be obtained in which the amount of octamethylcyclotetrasiloxane contained in the organopolysiloxane is 3,000 ppm or less. It is also described that by adding a trialkoxysiloxane to this emulsion, it is possible to introduce branch units into the resulting organopolysiloxane chain. However, when a high-viscosity organopolysiloxane is reacted with a trialkoxysilane, due to the difference in reactivity between the resulting organopolysiloxane whose molecular chain ends are blocked with silanol groups and the trialkoxysilane, the branching units are not uniformly incorporated into the siloxane chain, and the resulting organopolysiloxane chain does not increase in viscosity.
Additionally, Patent Documents 2 and 3 describe a method in which an organopolysiloxane having an octamethylcyclotetrasiloxane content of 1,000 ppm or less and whose molecular chain ends are blocked with silanol groups is emulsified, and then emulsion polymerization is carried out in the presence of an acid catalyst at a temperature of less than 40° C.

On the other hand, regarding emulsion polymerization methods using base catalysts, Patent Documents 4 and 5 describe polymerization methods using ammonium salts as surfactants. However, the above patent documents make no mention whatsoever of the content of octamethylcyclotetrasiloxane.

　These prior art techniques use anionic surfactants and acid catalysts, or cationic surfactants and inorganic base catalysts. When organopolysiloxane emulsions are used in products such as cosmetics, personal care compositions, home care compositions, release agents, slipping agents, coating agents, fiber treatment agents, and resin modifiers, the use of ionic surfactants can often be problematic. That is, organopolysiloxane emulsions containing anionic surfactants may be less stable when mixed with other chemicals containing cationic surfactants, and organopolysiloxane emulsions containing cationic surfactants may be less stable when mixed with other chemicals containing anionic surfactants. That is, organopolysiloxane emulsions containing ionic surfactants such as anionic surfactants and cationic surfactants may be limited in the ionicity of the chemicals that can be blended.

Therefore, it is necessary to establish a method for producing a high-viscosity organopolysiloxane emulsion composition that suppresses the by-production of octamethylcyclotetrasiloxane contained in the organopolysiloxane, has small particle size, and has a branched structure with good stability over time, even when the composition does not contain an ionic surfactant.

Patent No. 5382273 JP 2016-166324 A JP 2017-48342 A Patent No. 4683203 JP 2021-95455 A

The object of the present invention is therefore to provide a method for producing a high-viscosity organopolysiloxane emulsion composition that suppresses the by-production of octamethylcyclotetrasiloxane contained in the organopolysiloxane, has a small particle size, and has good stability over time, even when it does not contain an ionic surfactant.

（式中、Ｒ^１は互いに独立に、置換もしくは非置換の炭素原子数１～２０の１価炭化水素基であり、Ｒ^２は独立に、水素原子又は置換もしくは非置換の炭素原子数１～２０の１価炭化水素基である。ｎはオルガノポリシロキサンの２５℃における粘度が１５ｍＰａ・ｓ以上１００，０００ｍＰａ・ｓ以下となる数である。）
（Ｂ）下記一般式（２）で表される、オルガノアルコキシシラン、その部分加水分解縮合物、又はそれらの混合物：０．２～２０質量部、

（式中、Ｒ^３は互いに独立に、水素原子又は置換もしくは非置換の炭素原子数１～１０の１価炭化水素基であり、Ｒ^４は互いに独立に、置換もしくは非置換の炭素原子数１～１０の１価炭化水素基である。ｍは３～４である。）
（Ｃ）非イオン性界面活性剤：２～３０質量部
及び、
（Ｄ－１）水：１～１０，０００質量部
を含む混合物を乳化して第１のエマルション組成物を調製し、
（ＩＩ）前記第１のエマルション組成物に、
（Ｄ－２）水：０～１０，０００質量部
を加えた後、
４０℃未満の温度で、（Ｅ）有機塩基触媒０．１～２０質量部の存在下、乳化重合して、生成するオルガノポリシロキサンの２５℃における粘度が３０万ｍＰａ・ｓ以上であり、該オルガノポリシロキサンに含まれるオクタメチルシクロテトラシロキサンの量が３，０００ｐｐｍ以下であり、かつ、目的のエマルション組成物のエマルション粒子の平均粒径を１μｍ以下とすることを特徴とするオルガノポリシロキサンエマルション組成物の製造方法を提供する。 In order to solve the above problems, the present invention provides
(I) (A) 100 parts by mass of an organopolysiloxane represented by the following general formula (1) and having an octamethylcyclotetrasiloxane content of 3,000 ppm or less:

(In the formula, R ¹ 's are each independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and R ^2's are each independently a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms. n is a number that provides a viscosity of the organopolysiloxane at 25° C. of 15 mPa·s or more and 100,000 mPa·s or less.)
(B) an organoalkoxysilane represented by the following general formula (2), a partial hydrolysis condensate thereof, or a mixture thereof: 0.2 to 20 parts by mass,

(In the formula, each R ³ is independently a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, and each R ⁴ is independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms; and m is 3 to 4.)
(C) a nonionic surfactant: 2 to 30 parts by mass; and
(D-1) A mixture containing 1 to 10,000 parts by mass of water is emulsified to prepare a first emulsion composition;
(II) The first emulsion composition,
(D-2) Water: 0 to 10,000 parts by mass is added,
The present invention provides a method for producing an organopolysiloxane emulsion composition, which comprises emulsion polymerization at a temperature below 40°C in the presence of 0.1 to 20 parts by mass of an organic base catalyst (E), such that the viscosity of the resulting organopolysiloxane at 25°C is 300,000 mPa·s or more, the amount of octamethylcyclotetrasiloxane contained in the organopolysiloxane is 3,000 ppm or less, and the average particle size of the emulsion particles in the target emulsion composition is 1 μm or less.

The method for producing an organopolysiloxane emulsion composition of the present invention can efficiently produce a high-viscosity organopolysiloxane emulsion composition that contains small emulsion particles and has good stability over time, while suppressing the by-production of octamethylcyclotetrasiloxane (D4) contained in the organopolysiloxane, even when an ionic surfactant is not included.

In this case, it is preferable to use, as component (A), an organopolysiloxane in which n in the general formula (1) is a number that results in a viscosity of the organopolysiloxane at 25°C of 15 mPa·s or more and 1,800 mPa·s or less.

When such an organopolysiloxane is used, emulsion polymerization can be carried out well to efficiently obtain the desired organopolysiloxane, and the amount of D4 produced as a by-product during polymerization can be reduced. In addition, the amount of emulsifier required to reduce the particle size of the resulting desired emulsion can be reduced.

It is also preferable to use the (B) component in an amount of 0.4 to 10 parts by mass.

By doing this, the viscosity of the desired organopolysiloxane becomes more suitable, and the strength and durability of the resulting coating is superior.

In addition, it is preferable to use one or more selected from tetramethylguanidine, diazabicycloundecene, diazabicyclononene, triazabicyclodecene, methyltriazabicyclodecene, and diazabicyclooctane as the organic base catalyst (E).

By using such component (E), the desired organopolysiloxane emulsion composition can be produced more efficiently.

It is also preferable to use 0.5 to 7 parts by mass of the (E) organic base catalyst per 100 parts by mass of component (A).

By using such an amount of component (E), the desired organopolysiloxane emulsion composition can be produced more efficiently.

In the present invention, it is possible to produce an organopolysiloxane emulsion composition without using an anionic surfactant, and it is also possible to produce an organopolysiloxane emulsion composition without using a cationic surfactant.

This manufacturing method makes it possible to produce an organopolysiloxane emulsion composition that does not contain ionic surfactants, and since its stability is not reduced even when it is mixed with ionic drugs, there are no restrictions on the ionicity of the drugs that can be mixed.

In the present invention, it is preferable to carry out the emulsion polymerization of (II) above at a temperature of less than 25°C, and it is also preferable to limit the polymerization time to 48 hours or less.

　If emulsion polymerization is performed at such a temperature and/or polymerization time, the amount of D4 produced as a by-product can be reduced.

In addition, in the present invention, it is preferable that the average particle size of the emulsion particles in the intended emulsion composition is 500 nm or less.

According to the present invention, it is possible to efficiently obtain emulsion particles with such small particle sizes.

In addition, it is preferable that the content of octamethylcyclotetrasiloxane (D4) contained in the organopolysiloxane in the intended emulsion composition is 2,000 ppm or less.

According to the present invention, such an emulsion composition with a low D4 content can be obtained efficiently.

According to the present invention, even if an ionic surfactant is not used, it is possible to suppress the by-production of octamethylcyclotetrasiloxane contained in the organopolysiloxane, and obtain a high-viscosity organopolysiloxane emulsion composition with small particle size and good stability over time.

As a result of intensive research into achieving the above object, the inventors discovered that by using a linear organopolysiloxane and an organoalkoxysilane with an octamethylcyclotetrasiloxane content of 3,000 ppm or less as emulsion polymerization monomers and using an organic base as a polymerization catalyst, it is possible to obtain an emulsion composition in which the amount of octamethylcyclotetrasiloxane contained in the organopolysiloxane is 3,000 ppm or less, the average particle size of the emulsion particles is a very small particle size of 1 μm or less, and the stability over time is good, thereby completing the present invention.

（式中、Ｒ^１は互いに独立に、置換もしくは非置換の炭素原子数１～２０の１価炭化水素基であり、Ｒ^２は独立に、水素原子又は置換もしくは非置換の炭素原子数１～２０の１価炭化水素基である。ｎはオルガノポリシロキサンの２５℃における粘度が１５ｍＰａ・ｓ以上１００，０００ｍＰａ・ｓ以下となる数である。）
（Ｂ）下記一般式（２）で表される、オルガノアルコキシシラン、その部分加水分解縮合物、又はそれらの混合物：０．２～２０質量部、

（式中、Ｒ^３は互いに独立に、水素原子又は置換もしくは非置換の炭素原子数１～１０の１価炭化水素基であり、Ｒ^４は互いに独立に、置換もしくは非置換の炭素原子数１～１０の１価炭化水素基である。ｍは３～４である。）
（Ｃ）非イオン性界面活性剤：２～３０質量部
及び、
（Ｄ－１）水：１～１０，０００質量部
を含む混合物を乳化して第１のエマルション組成物を調製し、
（ＩＩ）前記第１のエマルション組成物に、
（Ｄ－２）水：０～１０，０００質量部
を加えた後、
４０℃未満の温度で、（Ｅ）有機塩基触媒０．１～２０質量部の存在下、乳化重合して、生成するオルガノポリシロキサンの２５℃における粘度が３０万ｍＰａ・ｓ以上であり、該オルガノポリシロキサンに含まれるオクタメチルシクロテトラシロキサンの量が３，０００ｐｐｍ以下であり、かつ、目的のエマルション組成物のエマルション粒子の平均粒径を１μｍ以下とすることを特徴とするオルガノポリシロキサンエマルション組成物の製造方法である。 That is, the present invention provides a composition comprising: (I) 100 parts by mass of an organopolysiloxane represented by the following general formula (1) and having an octamethylcyclotetrasiloxane content of 3,000 ppm or less;

(In the formula, R ¹ 's are each independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and R ^2's are each independently a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms. n is a number that provides a viscosity of the organopolysiloxane at 25° C. of 15 mPa·s or more and 100,000 mPa·s or less.)
(B) an organoalkoxysilane represented by the following general formula (2), a partial hydrolysis condensate thereof, or a mixture thereof: 0.2 to 20 parts by mass,

(In the formula, each R ³ is independently a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, and each R ⁴ is independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms; and m is 3 to 4.)
(C) a nonionic surfactant: 2 to 30 parts by mass; and
(D-1) A mixture containing 1 to 10,000 parts by mass of water is emulsified to prepare a first emulsion composition;
(II) The first emulsion composition,
(D-2) Water: 0 to 10,000 parts by mass is added,
This method for producing an organopolysiloxane emulsion composition is characterized by carrying out emulsion polymerization in the presence of 0.1 to 20 parts by mass of an organic base catalyst (E) at a temperature of less than 40°C, producing an organopolysiloxane having a viscosity at 25°C of 300,000 mPa s or more, containing octamethylcyclotetrasiloxane in an amount of 3,000 ppm or less, and having an average emulsion particle size of 1 μm or less in the target emulsion composition.

The present invention is described in detail below, but is not limited to these.

The method for producing an organopolysiloxane emulsion composition of the present invention comprises a step (I) of preparing a first emulsion composition, and a step (II) of emulsion polymerizing the first emulsion composition to obtain the desired emulsion composition.
In the step (I), a mixture containing (A) a specific organopolysiloxane, (B) a specific organoalkoxysilane, (C) a nonionic surfactant, and (D-1) water is emulsified to prepare a first emulsion composition.
In the step (II), water (D-2) is added, if necessary, to the first emulsion composition prepared in the step (I), and then the mixture is emulsion-polymerized in the presence of an organic base catalyst (E) at a temperature of less than 40° C. to obtain a target emulsion composition.
Each step will be described below.

（式中、Ｒ^１は互いに独立に、置換もしくは非置換の炭素原子数１～２０の１価炭化水素基であり、Ｒ^２は独立に、水素原子又は置換もしくは非置換の炭素原子数１～２０の１価炭化水素基である。ｎはオルガノポリシロキサンの２５℃における粘度が１５ｍＰａ・ｓ以上１００，０００ｍＰａ・ｓ以下となる数である。） The raw materials used in the production method of the present invention will now be described.
In the present invention, the viscosity is a value measured at 25° C. using a BM type or BH type rotational viscometer.
<(A) Organopolysiloxane>
The organopolysiloxane (A) of the present invention is represented by the following general formula (1) and has an octamethylcyclotetrasiloxane (D4) content of 3,000 ppm or less.

(In the formula, R ¹ 's are each independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and R ^2's are each independently a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms. n is a number that provides a viscosity of the organopolysiloxane at 25° C. of 15 mPa·s or more and 100,000 mPa·s or less.)

Each R ¹ is independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms. Examples of the unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms include an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and an aralkyl group having 7 to 20 carbon atoms. Specific examples include alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, and octadecyl groups; cycloalkyl groups such as cyclopentyl and cyclohexyl groups; alkenyl groups such as vinyl, allyl, and hexenyl groups; and aryl groups such as phenyl, tolyl, and naphthyl groups. Examples of the substituted monovalent hydrocarbon group having 1 to 20 carbon atoms include the above-listed monovalent hydrocarbon groups having 1 to 20 carbon atoms in which some of the hydrogen atoms have been substituted with halogen atoms such as F or Cl, amino groups, acryloxy groups, methacryloxy groups, epoxy groups, mercapto groups, carboxyl groups, hydroxyl groups, etc. Preferred are monovalent hydrocarbon groups having 1 to 6 carbon atoms, such as methyl groups, ethyl groups, propyl groups, butyl groups, and phenyl groups. More preferred are those in which 80% or more of all R ^1s are methyl groups.

^R2 is independently a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms. Examples of the unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms include an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and an aralkyl group having 7 to 20 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, a dodecyl group, a tetradecyl group, a hexadecyl group, and an octadecyl group; a cycloalkyl group such as a cyclopentyl group and a cyclohexyl group; an alkenyl group such as a vinyl group, an allyl group, and a hexenyl group; and an aryl group such as a phenyl group, a tolyl group, and a naphthyl group. Examples of the substituted monovalent hydrocarbon group having 1 to 20 carbon atoms include those in which some of the hydrogen atoms in the above-listed monovalent hydrocarbon groups having 1 to 20 carbon atoms have been substituted with halogen atoms such as F or Cl, amino groups, acryloxy groups, methacryloxy groups, epoxy groups, mercapto groups, carboxyl groups, hydroxyl groups, etc. Preferred are monovalent hydrocarbon groups having 1 to 6 carbon atoms, such as methyl groups, ethyl groups, propyl groups, butyl groups, and phenyl groups. ^R2 is preferably a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

In general formula (1), n is a number that gives the organopolysiloxane a viscosity at 25°C of 15 mPa·s or more and 100,000 mPa·s or less, and can be a number that gives 15 mPa·s or more and 1,800 mPa·s or less. n is particularly preferably a number that gives 100 mPa·s or more and 3,000 mPa·s or less, and most preferably a number that gives 500 to 1,800 mPa·s. A number that gives 500 to 800 mPa·s is even more preferable. If the viscosity is less than 15 mPa·s, it may be necessary to extend the emulsion polymerization time in order to give the organopolysiloxane contained in the target emulsion a desired viscosity, or the amount of octamethylcyclotetrasiloxane produced as a by-product during emulsion polymerization may increase. On the other hand, if the viscosity exceeds 100,000 mPa·s, a large amount of emulsifier is required to reduce the particle size of the target emulsion obtained, which is not preferable.

The content of octamethylcyclotetrasiloxane in the organopolysiloxane of component (A) is 3,000 ppm or less (by mass, the same applies below), particularly preferably 1,000 ppm or less, and more preferably 500 ppm or less. There is no particular lower limit, and it may be 0 ppm.
In order to ensure that the amount of D4 contained in the organopolysiloxane in the target emulsion composition is 3,000 ppm or less, the D4 content in the organopolysiloxane of component (A) must be 3,000 ppm by mass or less.

（式中、Ｒ^３は互いに独立に、水素原子又は置換もしくは非置換の炭素原子数１～１０の１価炭化水素基であり、Ｒ^４は互いに独立に、置換もしくは非置換の炭素原子数１～１０の１価炭化水素基である。ｍは３～４である。） <(B) Organoalkoxysilane>
The organoalkoxysilane (B) of the present invention is an organoalkoxysilane represented by the following general formula (2), a partial hydrolysis condensate thereof, or a mixture thereof.

(In the formula, each R ³ is independently a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, and each R ⁴ is independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms; and m is 3 to 4.)

^R3 are each independently a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms. Examples of the unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms include an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aralkyl group having 7 to 10 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group, a cycloalkyl group such as a cyclopentyl group and a cyclohexyl group, an alkenyl group such as a vinyl group, an allyl group, and a hexenyl group, and an aryl group such as a phenyl group, a tolyl group, and a naphthyl group. Examples of substituted monovalent hydrocarbon groups having 1 to 10 carbon atoms include those in which some of the hydrogen atoms in the above-listed monovalent hydrocarbon groups having 1 to 10 carbon atoms have been substituted with halogen atoms such as F or Cl, amino groups, acryloxy groups, methacryloxy groups, epoxy groups, mercapto groups, carboxyl groups, hydroxyl groups, etc. Preferred are hydrogen atoms or monovalent hydrocarbon groups having 1 to 6 carbon atoms, such as methyl groups, ethyl groups, propyl groups, butyl groups, and phenyl groups. Particularly preferred are hydrogen atoms, methyl groups, ethyl groups, and propyl groups.

^Each R4 is independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms. Examples of the unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms include an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aralkyl group having 7 to 10 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group, a cycloalkyl group such as a cyclopentyl group and a cyclohexyl group, an alkenyl group such as a vinyl group, an allyl group, and a hexenyl group, and an aryl group such as a phenyl group, a tolyl group, and a naphthyl group. Examples of substituted monovalent hydrocarbon groups having 1 to 10 carbon atoms include those in which some of the hydrogen atoms in the above-listed monovalent hydrocarbon groups having 1 to 10 carbon atoms have been substituted with halogen atoms such as F or Cl, amino groups, acryloxy groups, methacryloxy groups, epoxy groups, mercapto groups, carboxyl groups, hydroxyl groups, etc. Preferred are monovalent hydrocarbon groups having 1 to 6 carbon atoms, such as methyl groups, ethyl groups, propyl groups, butyl groups, and phenyl groups, and examples of substituted groups include 3-aminopropyl groups, N-(2-aminoethyl)-3-aminopropyl groups, 3-glycidoxypropyl groups, trifluoromethyl groups, and 3,3,3-trifluoropropyl groups. Methyl groups, ethyl groups, propyl groups, and phenyl groups are particularly preferred.

m is 3 to 4. It is particularly preferable that m is 3.

Specific examples of the component (B) include, but are not limited to, the following:
Methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, propyltrimethoxysilane, propyltriethoxysilane, butyltrimethoxysilane, butyltriethoxysilane, hexyltrimethoxysilane, hexyltriethoxysilane, octyltrimethoxysilane, octyltriethoxysilane, isooctyltrimethoxysilane, isooctyltriethoxysilane, 2-ethylhexyltrimethoxysilane, 2-ethylhexyltriethoxysilane, decyltrimethoxysilane, decyltriethoxy Examples of the silane include phenyltrimethoxysilane, phenyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, trifluoromethyltrimethoxysilane, and 3,3,3-trifluoropropyltrimethoxysilane.

As the component (B), methyltrimethoxysilane, methyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, and 3-aminopropyltriethoxysilane are more preferable, and methyltrimethoxysilane, phenyltrimethoxysilane, and phenyltriethoxysilane are particularly preferable.
The organoalkoxysilanes may be used alone or in combination of two or more.

As component (B) of the present invention, an oligomer or polymer obtained by hydrolyzing a portion of the alkoxy groups of the organoalkoxysilane and subjecting it to an intermolecular condensation reaction (hereinafter referred to as a partial hydrolysis condensate) may be used. Also, the organoalkoxysilane may be used in combination with the partial hydrolysis condensate of the organoalkoxysilane. The partial hydrolysis condensate of the organoalkoxysilane may be synthesized by subjecting the organoalkoxysilane to hydrolysis and condensation reaction in the presence of an acid catalyst or an alkali catalyst.

The amount of component (B) is 0.2 to 20 parts by mass per 100 parts by mass of component (A). It is preferably 0.4 to 10 parts by mass, more preferably 0.5 to 7.5 parts by mass, and particularly preferably 1 to 5 parts by mass.

<(C) Nonionic Surfactant>
The component (C) is a nonionic surfactant. One type may be used alone, or two or more types may be used in combination.

Examples of nonionic surfactants include polyoxyalkylene alkyl ethers such as polyoxyethylene alkyl ethers, polyoxyethylene polyoxypropylene alkyl ethers, and polyoxyethylene alkylphenyl ethers, polyethylene glycol fatty acid esters, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbit fatty acid esters, glycerin fatty acid esters, polyoxyethylene glycerin fatty acid esters, polyglycerin fatty acid esters, propylene glycol fatty acid esters, fatty acid esters such as polyoxyethylene castor oil, polyoxyethylene hydrogenated castor oil, and polyoxyethylene hydrogenated castor oil fatty acid esters, polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, polyoxyethylene modified organopolysiloxanes, and polyoxyethylene polyoxypropylene modified organopolysiloxanes. Commercially available products such as Newcol 1310 (manufactured by Nippon Nyukazai Co., Ltd.) may also be used.
Among these, polyoxyethylene alkyl ether and polyoxyethylene polyoxypropylene alkyl ether are preferred. The alkyl group may be either a straight chain or a branched chain.

From the viewpoint of emulsion stability, the nonionic surfactant (when a plurality of surfactants are used, the HLB value of the entire mixture) preferably has an HLB value in the range of 9.0 to 18.0, more preferably 10.0 to 17.0, and even more preferably 11.0 to 16.0. The HLB value is a value calculated by the Griffin method. The HLB value is calculated by the following formula.
N = N1 x W1 + N2 x W2
N: HLB value when two types of surfactants with different HLB values are used N1, N2: HLB value of each surfactant W1, W2: mass fraction of each surfactant (W1 + W2 = 1)

In addition to the nonionic surfactant (C), the composition of the present invention can also contain ionic surfactants such as cationic surfactants and anionic surfactants.

Examples of anionic surfactants include alkyl sulfate salts such as sodium lauryl sulfate, polyoxyethylene alkyl ether sulfate salts, polyoxyethylene alkyl phenyl ether sulfate salts, alkyl benzene sulfonates, polyoxyethylene alkyl phenyl ether sulfonates, alkyl diphenyl ether disulfonates, alkanesulfonates, N-acyltaurate salts, dialkyl sulfosuccinate salts, monoalkyl sulfosuccinate salts, polyoxyethylene alkyl ether sulfosuccinate salts, fatty acid salts, polyoxyethylene alkyl ether carboxylate salts, N-acyl amino acid salts, monoalkyl phosphate salts, dialkyl phosphate salts, polyoxyethylene alkyl ether phosphate salts, etc.

Cationic surfactants include quaternary ammonium salts such as alkyltrimethylammonium salts, dialkyldimethylammonium salts, polyoxyethylenealkyldimethylammonium salts, dipolyoxyethylenealkylmethylammonium salts, tripolyoxyethylenealkylammonium salts, and alkylbenzyldimethylammonium salts, as well as alkylpyridinium salts, monoalkylamine salts, and monoalkylamidoamine salts.

The ionic surfactant may be an amphoteric surfactant such as an alkylbetaine or an alkylimidazoline.

The organopolysiloxane emulsion composition of the present invention may contain an ionic surfactant if necessary, but as mentioned above, the use of cationic or anionic surfactants may reduce stability when mixed with ionic chemicals such as shampoo, so it is preferable not to use cationic or anionic surfactants in the method for producing the composition of the present invention.

The amount of component (C) used is 2 to 30 parts by weight per 100 parts by weight of component (A), preferably 4 to 20 parts by weight, and more preferably 5 to 15 parts by weight.

<(D) Water>
The water of the component (D) is (D-1) used in step (I) and, if necessary, (D-2) used in step (II).
In step (I), the amount of water used as component (D-1) is 1 to 10,000 parts by mass per 100 parts by mass of (A), and can vary depending on the type of emulsifier used to reduce the particle size of the emulsion particles.

For example, when using a high-pressure homogenizer that uses high pressure to reduce the size of emulsion particles (such as an emulsifier that pressurizes a treatment liquid to high or ultra-high pressure and passes it through a slit to obtain shear force, or an emulsifier that causes pressurized treatment liquids to collide obliquely with each other at ultra-high speed to form fine particles), the amount of component (D-1) used is preferably 2 to 8,000 parts by mass, more preferably 4 to 6,000 parts by mass, and even more preferably 6 to 4,000 parts by mass per 100 parts by mass of component (A).

In addition, when using emulsifiers such as a homodisper (an emulsifier that uses shearing force to reduce the emulsion particle size by rotating a circular disk with saw-tooth teeth on the periphery at high speed to generate shearing force), a homomixer (an emulsifier that has a stator installed on the periphery and rotates a rotor installed inside at high speed to generate shearing force), or a colloid mill (an emulsifier that feeds each component into the gap between a disk that rotates at high speed and a fixed disk to generate shearing force to emulsify), the amount of component (D-1) used is preferably 1 to 30 parts by mass, more preferably 2 to 25 parts by mass, and even more preferably 5 to 20 parts by mass, per 100 parts by mass of component (A). Here, if the amount is 30 parts by mass or less, it becomes easy to obtain an emulsion composition with a small average particle size of 1 μm or less, and if the amount is 1 part by mass or more, it is easy to obtain an O/W type emulsion.

In step (II), water as component (D-2) may or may not be added, and is preferably added in an amount of 10,000 parts by mass or less (0 to 10,000 parts by mass) relative to 100 parts by mass of component (A). When component (D-2) is added, the amount is preferably 0.1 to 1,000 parts by mass. Note that water as component (D-2) is preferably added when an emulsifier such as a homodisper, homomixer, or colloid mill is normally used.
The total amount of component (D) (total amount of (D-1) and (D-2)) can be 30 to 10,000 parts by mass per 100 parts by mass of component (A).

<(E) Organic Base Catalyst>
The component (E) is an organic base catalyst. The organic base catalyst (hereinafter also referred to as "organic base") is not particularly limited as long as it is an organic electron pair donor (so-called Lewis base). The structure of the organic base is also not particularly limited, and may be saturated or unsaturated, linear or branched, or any cyclic structure having three or more members, and the cyclic structure may be one ring or two or more rings. The organic base may contain one or more heteroatoms such as nitrogen, oxygen, sulfur, and phosphorus in the molecule, and when two or more heteroatoms are contained, the heteroatoms may be the same or different.
Examples of the organic base include amines, quaternary ammonium hydroxides such as tetramethylammonium hydroxide, phosphorus-based phosphazene bases such as guanidinophosphazene, and amino acids.
The amine may be any of primary amines, secondary amines, and tertiary amines, and may be any of aliphatic amines, aromatic amines, heterocyclic amines, alkanolamines, and ether amines. Among them, linear, branched, or cyclic tertiary amines are preferred. The tertiary amines include those having one or more tertiary nitrogens in the molecule. The number of carbon atoms in the amine is not particularly limited, but may be, for example, C1 to C30, and preferably C4 to C25.
The component (E) can use either a single compound or a suitable combination of two or more different compounds.

Specific examples of the component (E) include, but are not limited to, the following.
trialkylamines such as triethylamine, diisopropylethylamine (DIPEA), tri-n-butylamine, tri-n-pentylamine, tri-n-hexylamine, tri-n-heptylamine, and tri-n-octylamine; N-alkyl cyclic amines such as N-methylpyrrolidine and N-methylpiperidine; N-alkyl cyclic ether amines such as N-methylmorpholine; N-alkyl diamines such as N,N,N',N'-tetramethylethylenediamine (TMEDA); N-alkyl imidazoles such as N-methylimidazole (NMI); 1,8-diazabicyclo-[5.4.0]-7-undecene (DBU), 1,5-diazabicyclo[4.3.0]nonene-5 (DBN), 1,4-diazabicyclo-[2.2.2. ]octane (DABCO), alkylpyridines such as pyridine, 2,6-lutidine, and 1,3,5-collidine, aminopyridines such as N,N-dimethylaminopyridine (DMAP), triazabicyclo compounds such as pyrazine, quinoline, 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), and 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD), and guanidine compounds such as 1,1,3,3-tetramethylguanidine (TMG).

The (E) component is preferably a non-ionic organic base catalyst, and one or more selected from tetramethylguanidine, diazabicycloundecene, diazabicyclononene, triazabicyclodecene, methyltriazabicyclodecene, and diazabicyclooctane can be used. DBN, DBU, TBD, MTBD, DABCO, and 1,1,3,3-tetramethylguanidine are more preferred, with DBN and DBU being particularly preferred.

In particular, nonionic organic bases such as tetramethylguanidine, diazabicycloundecene, diazabicyclononene, triazabicyclodecene, methyltriazabicyclodecene, and diazabicyclooctane are highly basic. This promotes the condensation reaction between the hydrolyzable organopolysiloxane of component (A) and the organoalkoxysilane of component (B) (as a source of T units and/or D units), and also reduces the ionicity of the emulsion composition due to its high proton capture ability even when neutralized after the emulsion polymerization is completed. Due to this action, it is believed that the emulsion composition of the present invention can maintain a stable emulsion for a long time even when used in products containing ionic drugs.

The amount of component (E) used is 0.1 to 20 parts by mass per 100 parts by mass of component (A). It is preferably 0.3 to 15 parts by mass, more preferably 0.5 to 10 parts by mass, even more preferably 0.5 to 7 parts by mass, and particularly preferably 0.7 to 5 parts by mass.

The production method of the present invention will now be described.
<Step (I)>
The mixture containing the above-mentioned (A), (B), (C) and (D) components is emulsified to prepare an emulsion composition. The emulsification here can be performed using emulsifiers such as homodisper, homomixer, colloid mill, line mixer, universal mixer, ultramixer, planetary mixer, combimix, high-pressure homogenizer, etc., and preferably, homodisper, homomixer, colloid mill, etc., which use shear force to reduce the emulsion particles, and more preferably, homodisper.

In this process, the emulsification temperature is preferably 1 to 80°C, and it is more preferable to carry out the emulsification at a temperature below 25°C.

In this step (I), the mixture is mixed under high shear force until the average particle size of the emulsion particles in the emulsion composition is preferably 1 μm or less, more preferably 800 nm or less, and even more preferably 500 nm or less. The smaller the particle size of the emulsion particles obtained in step (I), the higher the polymerization rate in step (II), which leads to a reduction in the polymerization time. Furthermore, as a result of the particle size of the emulsion particles in the emulsion composition obtained in step (I) being 500 nm or less, the particle size of the final emulsion particles obtained in the next step is also 500 nm or less. In the present invention, the particle size of the emulsion particles is the median size (volume basis) measured using a laser diffraction/scattering particle size distribution analyzer LA-960 (manufactured by Horiba, Ltd.).

<Step (II)>
To the obtained emulsion composition, water (D-2) may be added as necessary to disperse it, and then component (E) is added at a temperature of less than 40°C to carry out emulsion polymerization until the viscosity of the organopolysiloxane in the emulsion composition at 25°C is 300,000 mPa s or more and the average particle size of the emulsion particles in the intended emulsion composition is 1 µm or less.

When the emulsion composition is emulsion-polymerized, it is recommended that the polymerization step be carried out at a temperature of less than 40°C for 48 hours or less. If the polymerization is carried out at a temperature of 40°C or more, there is a risk that a large amount of octamethylcyclotetrasiloxane is produced. Therefore, it is preferably less than 25°C, and more preferably less than 20°C. The lower limit temperature is not particularly limited, but can be 4°C or more from the viewpoint of productivity. In addition, if the polymerization time is 48 hours or less, the amount of octamethylcyclotetrasiloxane by-produced is small, so that 1 to 40 hours is preferable, and 5 to 30 hours is more preferable.
The emulsification means can be any of those listed in step (I). It is preferable to use an emulsifier that uses shear force to reduce the emulsion particles, and it is more preferable to dilute and disperse the emulsion using a homomixer.

<Other Processing>
After the polymerization is completed, the resulting emulsion composition can usually be neutralized with an acidic substance, such as hydrochloric acid, formic acid, acetic acid, propionic acid, citric acid, etc. Instead of using an acidic substance, it is also possible to neutralize the composition using an ion exchange resin.
At this time, water can be added to adjust the silicone concentration, and a preservative or the like can be added to improve the shelf life of the emulsion composition.

The viscosity of the organopolysiloxane obtained by the manufacturing method of the present invention is a measured value when measured at 25°C using a BM-type or BH-type rotational viscometer. For those that could be measured in liquid form, this viscosity was measured as is, and for those that were too viscous to measure, the viscosity was measured after dissolving in 5% or 10% toluene. For those that were too viscous to measure even after dilution with toluene, those that wrapped around the rotor of the BM-type or BH-type rotational viscometer and could not be measured, or those that did not dissolve in toluene and could not be measured, the viscosity was all 300,000 mPa·s or more.

In the present invention, the average particle size of the emulsion particles in the target emulsion composition is 1 μm or less, preferably 800 nm or less, and particularly preferably 500 nm or less. There is no particular lower limit, but it is about 30 nm or more. According to the present invention, the average particle size of the emulsion particles in the emulsion composition is 1 μm or less, and very fine particles are obtained. The average particle size of the emulsion particles is the median diameter value measured by the laser diffraction/scattering method.

The content of octamethylcyclotetrasiloxane in the organopolysiloxane is 3,000 ppm or less, preferably 2,000 ppm or less, and more preferably 1,000 ppm or less. There is no particular lower limit, but it is 0 ppm or more.

As described above, according to the present invention, even in the absence of an ionic surfactant, it is possible to efficiently produce a high-viscosity (high degree of polymerization) organopolysiloxane emulsion composition that suppresses the by-production of octamethylcyclotetrasiloxane contained in the organopolysiloxane and has a branched structure with small particle size and good stability over time.
Specifically, a linear organopolysiloxane having an octamethylcyclotetrasiloxane content of 3,000 ppm or less is used as the emulsion polymerization monomer, an organoalkoxysilane as a source of T units and/or Q units, and a nonionic surfactant are used, and an organic base is used as the polymerization catalyst; the mixture is emulsified and polymerized, whereby it is possible to obtain an organopolysiloxane emulsion composition having an extremely small average particle size of 1 μm or less while keeping the amount of octamethylcyclotetrasiloxane contained in the organopolysiloxane in the emulsion composition to 3,000 ppm or less.
The present invention is capable of producing an organopolysiloxane emulsion composition while suppressing the generation of low molecular weight cyclic siloxanes, and there is little possibility that the siloxanes will volatilize and contaminate the inside of the equipment during heat treatment or the like, and therefore the present invention is highly industrially useful.

In the present invention, the organopolysiloxane produced by emulsion polymerization has a high viscosity of at least 300,000 mPa·s at 25° C., and branching units are uniformly introduced into the resulting organopolysiloxane chain.
In particular, the present invention has the excellent feature that the emulsion composition of the present invention can be prepared by emulsion polymerization without the use of an ionic surfactant, and thus the stability is not reduced when the composition is mixed with other drugs containing an ionic surfactant, and the composition is not limited by the ionicity of the drugs that can be mixed. Furthermore, the use of a nonionic organic base catalyst can reduce the total amount of ionic components in the resulting composition, and therefore the emulsion composition of the present invention can be applied to a wider range of applications.

The present invention will be specifically explained below with examples and comparative examples, but the present invention is not limited to the following examples. "Parts" means parts by mass. Viscosity is a value measured at 25°C using a BM type or BH type rotational viscometer.

[Example 1]
100 parts of (A-1) organopolysiloxane having a silanol group at the molecular chain end and a viscosity of 680 mPa·s (in general formula (1), R ¹ = methyl group, R ² = hydrogen atom, octamethylcyclotetrasiloxane content of 50 ppm or less), 2.4 parts of (B-1) phenyltriethoxysilane, 13.5 parts of (C-1) Newcol 1310 (trade name, manufactured by Nippon Nyukazai Co., Ltd., polyoxyethylene tridecyl ether, HLB value = 13.7), and 11.3 parts of (D-1) water were emulsified using a homodisper. After emulsification, shear was applied using a homodisper to reduce the particle size of the emulsion. 109.3 parts of (D-2) water were added to the obtained first emulsion, and the mixture was diluted and dispersed using a homomixer. Next, after cooling to 15°C, 2.5 parts of (E-1) 1,5-diazabicyclo[4.3.0]nonene-5 (DBN) were added, and emulsion polymerization was carried out at 15°C for 24 hours. Thereafter, 1.8 parts of acetic acid were added to the obtained emulsion, and the mixture was diluted and dispersed using a homomixer to obtain an emulsion composition. The results are shown in Table 1.

[Example 2]
100 parts of (A-1) organopolysiloxane having a silanol group at the molecular chain end and a viscosity of 680 mPa·s (in general formula (1), R ¹ = methyl group, R ² = hydrogen atom, octamethylcyclotetrasiloxane content of 50 ppm or less), 2.4 parts of (B-1) phenyltriethoxysilane, 12.4 parts of (C-1) Newcol 1310, and 10.8 parts of (D-1) water were emulsified using a homodisper. After emulsification, shear was applied using a homodisper to reduce the particle size of the emulsion. 110.9 parts of (D-2) water were added to the obtained first emulsion, and the mixture was diluted and dispersed using a homomixer. Next, after cooling to 15° C., 1.3 parts of (E-1) 1,5-diazabicyclo[4.3.0]nonene-5 (DBN) were added, and emulsion polymerization was carried out at 15° C. for 24 hours. Thereafter, 0.9 parts of acetic acid was added to the obtained emulsion, and the mixture was diluted and dispersed using a homomixer to obtain an emulsion composition. The results are shown in Table 1.

[Example 3]
100 parts of (A-1) organopolysiloxane having a silanol group at the molecular chain end and a viscosity of 680 mPa·s (in general formula (1), R ¹ = methyl group, R ² = hydrogen atom, octamethylcyclotetrasiloxane content of 50 ppm or less), 2.4 parts of (B-1) phenyltriethoxysilane, 12.4 parts of (C-1) Newcol 1310, and 10.8 parts of (D-1) water were emulsified using a homodisper. After emulsification, shear was applied using a homodisper to reduce the particle size of the emulsion. 110.9 parts of (D-2) water were added to the obtained first emulsion, and the mixture was diluted and dispersed using a homomixer. Next, after cooling to 15° C., 1.6 parts of (E-2) 1,8-diazabicyclo-[5.4.0]-7-undecene (DBU) were added, and emulsion polymerization was carried out at 15° C. for 24 hours. Thereafter, 1.0 part of acetic acid was added to the obtained emulsion, and the mixture was diluted and dispersed using a homomixer to obtain an emulsion composition. The results are shown in Table 1.

[Example 4]
100 parts of (A-1) organopolysiloxane having a silanol group at the molecular chain end and a viscosity of 680 mPa·s (in general formula (1), R ¹ = methyl group, R ² = hydrogen atom, octamethylcyclotetrasiloxane content of 50 ppm or less), 2.4 parts of (B-1) phenyltriethoxysilane, 12.4 parts of (C-1) Newcol 1310, and 10.8 parts of (D-1) water were emulsified using a homodisper. After emulsification, shear was applied using a homodisper to reduce the particle size of the emulsion. 110.9 parts of (D-2) water were added to the obtained first emulsion, and the mixture was diluted and dispersed using a homomixer. Next, after cooling to 15° C., 1.2 parts of (E-3) 1,1,3,3-tetramethylguanidine (TMG) was added, and emulsion polymerization was carried out at 15° C. for 24 hours. Thereafter, 1.0 part of acetic acid was added to the obtained emulsion, and the mixture was diluted and dispersed using a homomixer to obtain an emulsion composition. The results are shown in Table 1.

[Example 5]
100 parts of (A-2) organopolysiloxane having a silanol group at the molecular chain end and a viscosity of 1,450 mPa·s (in general formula (1), R ¹ = a methyl group, R ² = a hydrogen atom, and an octamethylcyclotetrasiloxane content of 50 ppm or less), 2.4 parts of (B-1) phenyltriethoxysilane, 12.4 parts of (C-1) Newcol 1310, and 10.8 parts of (D-1) water were emulsified using a Homodisper. After emulsification, shear was applied using a Homodisper to reduce the particle size of the emulsion. 110.9 parts of (D-2) water were added to the obtained first emulsion, and the mixture was diluted and dispersed using a Homomixer. Next, after cooling to 15°C, 1.6 parts of (E-2) 1,8-diazabicyclo-[5.4.0]-7-undecene (DBU) were added, and emulsion polymerization was carried out at 15°C for 18 hours. Thereafter, 1.0 part of acetic acid was added to the obtained emulsion, and the mixture was diluted and dispersed using a homomixer to obtain an emulsion composition. The results are shown in Table 2.

[Example 6]
100 parts of (A-1) organopolysiloxane having a silanol group at the molecular chain end and a viscosity of 680 mPa·s (in general formula (1), R ¹ = methyl group, R ² = hydrogen atom, octamethylcyclotetrasiloxane content of 50 ppm or less), 1.8 parts of (B-2) methyltrimethoxysilane, 12.4 parts of (C-1) Newcol 1310, and 10.8 parts of (D-1) water were emulsified using a homodisper. After emulsification, shear was applied using a homodisper to reduce the particle size of the emulsion. 110.9 parts of (D-2) water were added to the obtained first emulsion, and the mixture was diluted and dispersed using a homomixer. Next, after cooling to 15° C., 1.6 parts of (E-2) 1,8-diazabicyclo-[5.4.0]-7-undecene (DBU) were added, and emulsion polymerization was carried out at 15° C. for 24 hours. Thereafter, 1.0 part of acetic acid was added to the obtained emulsion, and the mixture was diluted and dispersed using a homomixer to obtain an emulsion composition. The results are shown in Table 2.

[Example 7]
100 parts of (A-1) organopolysiloxane having a silanol group at the molecular chain end and a viscosity of 680 mPa·s (in general formula (1), R ¹ = methyl group, R ² = hydrogen atom, octamethylcyclotetrasiloxane content of 50 ppm or less), 1.5 parts of (B-1) phenyltriethoxysilane, 12.4 parts of (C-1) Newcol 1310, and 10.8 parts of (D-1) water were emulsified using a homodisper. After emulsification, shear was applied using a homodisper to reduce the particle size of the emulsion. 111.8 parts of (D-2) water were added to the obtained first emulsion, and the mixture was diluted and dispersed using a homomixer. Next, after cooling to 15° C., 1.6 parts of (E-2) 1,8-diazabicyclo-[5.4.0]-7-undecene (DBU) were added, and emulsion polymerization was carried out at 15° C. for 24 hours. Thereafter, 1.0 part of acetic acid was added to the obtained emulsion, and the mixture was diluted and dispersed using a homomixer to obtain an emulsion composition. The results are shown in Table 2.

[Example 8]
100 parts of (A-1) organopolysiloxane having a silanol group at the molecular chain end and a viscosity of 680 mPa·s (in general formula (1), R ¹ = methyl group, R ² = hydrogen atom, octamethylcyclotetrasiloxane content 50 ppm or less), 3.3 parts of (B-1) phenyltriethoxysilane, 0.7 parts of (B-3) N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 9.4 parts of (C-1) Newcol 1310, and 9.7 parts of (D-1) water were emulsified using a homodisper. After emulsification, shear was applied using a homodisper to reduce the particle size of the emulsion. 165.5 parts of (D-2) water were added to the obtained first emulsion, and the mixture was diluted and dispersed using a homomixer. Next, after cooling to 15°C, 4.7 parts of (E-2) 1,8-diazabicyclo-[5.4.0]-7-undecene (DBU) were added, and emulsion polymerization was carried out at 15°C for 24 hours. Thereafter, 3.7 parts of acetic acid were added to the obtained emulsion, and the mixture was diluted and dispersed using a homomixer to obtain an emulsion composition. The results are shown in Table 2.

[Comparative Example 1]
100 parts of (A-1) organopolysiloxane having a silanol group at the molecular chain end and a viscosity of 680 mPa·s (in general formula (1), R ¹ = methyl group, R ² = hydrogen atom, octamethylcyclotetrasiloxane content of 50 ppm or less), 2.4 parts of (B-1) phenyltriethoxysilane, 12.4 parts of (C-1) Newcol 1310, and 10.8 parts of (D-1) water were emulsified using a homodisper. After emulsification, shear was applied using a homodisper to reduce the particle size of the emulsion. 110.9 parts of (D-2) water were added to the obtained first emulsion, and the mixture was diluted and dispersed using a homomixer. Next, after cooling to 15° C., 5.6 parts of lactic acid was added, and emulsion polymerization was carried out at 15° C. for 24 hours. Thereafter, 35.4 parts of a 10% aqueous solution of sodium carbonate was added to the resulting emulsion, and the mixture was diluted and dispersed using a homomixer to obtain an emulsion composition. The results are shown in Table 3.

[Comparative Example 2]
100 parts of (A-1) organopolysiloxane having a silanol group at the molecular chain end and a viscosity of 680 mPa·s (in general formula (1), R ¹ = methyl group, R ² = hydrogen atom, octamethylcyclotetrasiloxane content of 50 ppm or less), 2.4 parts of (B-1) phenyltriethoxysilane, 13.5 parts of (C-1) Newcol 1310, and 11.3 parts of (D-1) water were emulsified using a homodisper. After emulsification, shear was applied using a homodisper to reduce the size of the emulsion. 109.3 parts of (D-2) water were added to the obtained first emulsion, and the emulsion was diluted and dispersed using a homomixer. Next, after cooling to 15° C., 3.6 parts of 30% ammonia water was added, and emulsion polymerization was carried out at 15° C. for 24 hours. Thereafter, 1.3 parts of acetic acid was added to the obtained emulsion, and the mixture was diluted and dispersed using a homomixer to obtain an emulsion composition. The results are shown in Table 3.

[Comparative Example 3]
100 parts of (A-1) organopolysiloxane having a viscosity of 680 mPa·s and a silanol group at the molecular chain end (general formula (1), R ¹ = methyl group, R ² = hydrogen atom, octamethylcyclotetrasiloxane content 50 ppm or less), 2.4 parts of (B-1) phenyltriethoxysilane, 13.5 parts of (C-1) Newcol 1310, and 11.3 parts of (D-1) water were emulsified using a homodisper. After emulsification, shear was applied using a homodisper to reduce the size of the emulsion. 101.04 parts of (D-2) water were added to the obtained first emulsion, and the emulsion was diluted and dispersed using a homomixer. Next, after cooling to 15° C., 5.8 parts of a 30% aqueous potassium hydroxide solution was added, and emulsion polymerization was carried out at 15° C. for 24 hours. Thereafter, 0.6 parts of acetic acid was added to the obtained emulsion, and the mixture was diluted and dispersed using a homomixer to obtain an emulsion composition. The results are shown in Table 3.

[Comparative Example 4]
100 parts of (A-1) organopolysiloxane having a silanol group at the molecular chain end and a viscosity of 680 mPa·s (in general formula (1), R ¹ = a methyl group, R ² = a hydrogen atom, and an octamethylcyclotetrasiloxane content of 50 ppm or less), 0.05 parts of (B-1) phenyltriethoxysilane, 12.4 parts of (C-1) Newcol 1310, and 10.8 parts of (D-1) water were emulsified using a Homodisper. After emulsification, shear was applied using a Homodisper to reduce the particle size of the emulsion. 110.9 parts of (D-2) water were added to the obtained first emulsion, and the mixture was diluted and dispersed using a Homomixer. Next, after cooling to 15°C, 1.6 parts of (E-2) 1,8-diazabicyclo-[5.4.0]-7-undecene (DBU) were added, and emulsion polymerization was carried out at 15°C for 24 hours. Thereafter, 1.0 part of acetic acid was added to the obtained emulsion, and the mixture was diluted and dispersed using a homomixer to obtain an emulsion composition. The results are shown in Table 3.

[Comparative Example 5]
100 parts of (A-1) organopolysiloxane having a silanol group at the molecular chain end and a viscosity of 680 mPa·s (in general formula (1), R ¹ = a methyl group, R ² = a hydrogen atom, and an octamethylcyclotetrasiloxane content of 50 ppm or less), 2.4 parts of (B-1) phenyltriethoxysilane, 12.4 parts of (C-1) Newcol 1310, and 10.8 parts of (D-1) water were emulsified using a Homodisper. After emulsification, shear was applied using a Homodisper to reduce the particle size of the emulsion. 110.9 parts of (D-2) water were added to the resulting first emulsion, and the mixture was diluted and dispersed using a Homomixer. Next, after cooling to 15°C, 25.0 parts of (E-2) 1,8-diazabicyclo-[5.4.0]-7-undecene (DBU) were added, and emulsion polymerization was carried out at 15°C for 24 hours. Thereafter, 15.6 parts of acetic acid were added to the obtained emulsion, and the mixture was diluted and dispersed using a homomixer to obtain an emulsion composition. The results are shown in Table 4.

[Comparative Example 6]
100 parts of (A-1) organopolysiloxane having a silanol group at the molecular chain end and a viscosity of 680 mPa·s (in general formula (1), R ¹ = methyl group, R ² = hydrogen atom, octamethylcyclotetrasiloxane content of 50 ppm or less), 2.4 parts of (B-1) phenyltriethoxysilane, 12.4 parts of (C-1) Newcol 1310, and 10.8 parts of (D-1) water were emulsified using a homodisper. After emulsification, shear was applied using a homodisper to reduce the particle size of the emulsion. 110.9 parts of (D-2) water were added to the obtained first emulsion, and the mixture was diluted and dispersed using a homomixer. Next, after cooling to 15° C., 1.2 parts of concentrated sulfuric acid was added, and emulsion polymerization was carried out at 15° C. for 24 hours. Thereafter, 20.9 parts of a 10% aqueous solution of sodium carbonate was added to the resulting emulsion, and the mixture was diluted and dispersed using a homomixer to obtain an emulsion composition. The results are shown in Table 4.

[Comparative Example 7]
100 parts of (A-1) organopolysiloxane having a silanol group at the molecular chain end and a viscosity of 680 mPa·s (in general formula (1), R ¹ = methyl group, R ² = hydrogen atom, octamethylcyclotetrasiloxane content of 50 ppm or less), 2.4 parts of (B-1) phenyltriethoxysilane, 12.4 parts of (C-1) Newcol 1310, and 10.8 parts of (D-1) water were emulsified using a homodisper. After emulsification, shear was applied using a homodisper to reduce the particle size of the emulsion. 110.9 parts of (D-2) water were added to the obtained first emulsion, and the mixture was diluted and dispersed using a homomixer. Next, after cooling to 15° C., 3.5 parts of dodecylbenzenesulfonic acid were added, and emulsion polymerization was carried out at 15° C. for 24 hours. Thereafter, 12.8 parts of a 10% aqueous solution of sodium carbonate was added to the resulting emulsion, and the mixture was diluted and dispersed using a homomixer to obtain an emulsion composition. The results are shown in Table 4.

The following properties of the emulsion compositions obtained in the above examples were measured or evaluated using the methods described below. The results are shown in Tables 1-4.

[Average particle size of emulsion]
The median diameter was measured using a laser diffraction/scattering particle size distribution analyzer LA-960 (manufactured by Horiba, Ltd.).

[Viscosity of Organopolysiloxane]
30 g of isopropyl alcohol was added to 30 g of the prepared emulsion composition while stirring, and the precipitated organopolysiloxane was separated and dried at 105 ° C for 3 hours, and the value was measured at 25 ° C with a BM type or BH type rotational viscometer. The viscosity was measured as it was in the liquid state, and the viscosity was measured as 5% toluene solution viscosity for the viscosity that was too high to measure. The viscosity was too high to measure even after dilution with 5% toluene, the viscosity was wrapped around the rotor of the BM type or BH type rotational viscometer and could not be measured, or the viscosity was not dissolved in toluene and could not be measured. When it was not possible to measure, all the viscosities were 300,000 mPa s or more. In Tables 1 and 2, the viscosity indicated with "(5% toluene)" means that the organopolysiloxane itself could not be measured, and was measured as a 5% toluene solution. In this case, the viscosity of the organopolysiloxane was 300,000 mPa s or more, which means a favorable result. The mark "measurable" means that it was difficult to prepare a 5% toluene solution and therefore measurement was not possible. In this case, the viscosity of the organopolysiloxane was 300,000 mPa·s or more, which means a particularly favorable result.

[Octamethylcyclotetrasiloxane (D4) Content in Organopolysiloxane]
0.1 g of the emulsion composition was extracted (shaken for 3 hours) with 10 mL of acetone containing 20 ppm (by mass) of tetradecane as an internal standard, and then the mixture was allowed to stand overnight. The acetone layer was then sampled and subjected to gas chromatography analysis to quantify the amount of octamethylcyclotetrasiloxane.

[Emulsion stability]
100 g of the emulsion composition was placed in a 100 mL glass bottle, and the appearance was observed after leaving it at 50° C. for 3 months. When the emulsion formed a uniform single phase and no separation was observed, the stability was evaluated as good and indicated by "○", and when separation into two phases was observed, the stability was evaluated as "poor" and indicated by "×".

According to the production method of the present invention (Examples 1 to 8), even in the absence of an ionic surfactant, it is possible to obtain an emulsion of high viscosity organopolysiloxane with an extremely low cyclic siloxane content, and it is possible to obtain an organopolysiloxane emulsion composition with a small average emulsion particle size and good stability over time.
On the other hand, when an organic base catalyst is not used (Comparative Examples 1 to 3, 6, and 7), the viscosity of the organopolysiloxane, the D4 content, and the emulsion stability cannot all be satisfied at the same time. In particular, when a base catalyst is used, when a weak inorganic base is used as the catalyst (Comparative Example 2), the viscosity of the resulting organopolysiloxane is low and the emulsion stability is also poor, and when a strong inorganic base is used as the catalyst (Comparative Example 3), the D4 content (amount of D4 produced as a by-product) is further increased.
Furthermore, even when an organic base catalyst is used, if the amount of component (B) used is small (Comparative Example 4), the viscosity of the resulting organopolysiloxane is low, whereas if too much of the organic base catalyst is used (Comparative Example 5), a high-viscosity organopolysiloxane is obtained, but the D4 content and emulsion stability are poor.

When a strong inorganic base or strong inorganic acid is used as a catalyst, the viscosity, D4 content, and emulsion stability of the organopolysiloxane all deteriorate (Comparative Examples 3 and 6), but this is thought to be because these catalysts promote the decomposition of the organopolysiloxane. On the other hand, in the present invention, even when a strongly basic compound such as DBU, DBN, or TMG is used as the organic base catalyst, the decomposition of the organopolysiloxane is suppressed and the above-mentioned excellent effects are achieved for the first time by the characteristic configuration of the present invention, which could not be predicted from the prior art.

[Industrial Applicability]
The production method of the present invention makes it possible to obtain a high-viscosity organopolysiloxane emulsion with an extremely low content of cyclic siloxane. During heat treatment, etc., there is little possibility that the cyclic siloxane will volatilize and contaminate the inside of the device, making it industrially useful. Furthermore, since it has excellent stability and usability, it is particularly useful as a cosmetic or household product, and can be used in hair care products such as shampoo and conditioner. It can also be used as a protective material for furniture and miscellaneous goods, a coating agent for rubber, plastic, concrete, mortar, wood, paper, etc., a mold release agent for molds used in processing rubber products and plastic products, and a fiber treatment agent for the purpose of imparting water repellency and flexibility to fibers.

（式中、Ｒ^１は互いに独立に、置換もしくは非置換の炭素原子数１～２０の１価炭化水素基であり、Ｒ^２は独立に、水素原子又は置換もしくは非置換の炭素原子数１～２０の１価炭化水素基である。ｎはオルガノポリシロキサンの２５℃における粘度が１５ｍＰａ・ｓ以上１００，０００ｍＰａ・ｓ以下となる数である。）
（Ｂ）下記一般式（２）で表される、オルガノアルコキシシラン、その部分加水分解縮合物、又はそれらの混合物：０．２～２０質量部、

（式中、Ｒ^３は互いに独立に、水素原子又は置換もしくは非置換の炭素原子数１～１０の１価炭化水素基であり、Ｒ^４は互いに独立に、置換もしくは非置換の炭素原子数１～１０の１価炭化水素基である。ｍは３～４である。）
（Ｃ）非イオン性界面活性剤：２～３０質量部
及び、
（Ｄ－１）水：１～１０，０００質量部
を含む混合物を乳化して第１のエマルション組成物を調製し、
（ＩＩ）前記第１のエマルション組成物に、
（Ｄ－２）水：０～１０，０００質量部
を加えた後、
４０℃未満の温度で、（Ｅ）有機塩基触媒０．１～２０質量部の存在下、乳化重合して、生成するオルガノポリシロキサンの２５℃における粘度が３０万ｍＰａ・ｓ以上であり、該オルガノポリシロキサンに含まれるオクタメチルシクロテトラシロキサンの量が３，０００ｐｐｍ以下であり、かつ、目的のエマルション組成物のエマルション粒子の平均粒径を１μｍ以下とすることを特徴とするオルガノポリシロキサンエマルション組成物の製造方法。
　［２］：前記（Ａ）成分として、前記一般式（１）のｎが、オルガノポリシロキサンの２５℃における粘度が１５ｍＰａ・ｓ以上１，８００ｍＰａ・ｓ以下となる数であるオルガノポリシロキサンを用いることを特徴とする［１］のオルガノポリシロキサンエマルション組成物の製造方法。
　［３］：前記（Ｂ）成分の含有量が０．４～１０質量部となるように用いることを特徴とする［１］又は［２］のオルガノポリシロキサンエマルション組成物の製造方法。
　［４］：前記（Ｅ）有機塩基触媒として、テトラメチルグアニジン、ジアザビシクロウンデセン、ジアザビシクロノネン、トリアザビシクロデセン、メチルトリアザビシクロデセン、ジアザビシクロオクタンから選ばれる１種以上を用いることを特徴とする［１］から［３］のいずれか１つのオルガノポリシロキサンエマルション組成物の製造方法。
　［５］：前記（Ｅ）有機塩基触媒を、（Ａ）成分１００質量部に対して、０．５～７質量部用いることを特徴とする［１］から［４］のいずれか１つのオルガノポリシロキサンエマルション組成物の製造方法。
　［６］：アニオン性界面活性剤を使用しないことを特徴とする［１］から［５］のいずれか１つのオルガノポリシロキサンエマルション組成物の製造方法。
　［７］：
　カチオン性界面活性剤を使用しないことを特徴とする［１］から［６］のいずれか１つのオルガノポリシロキサンエマルション組成物の製造方法。
　［８］：前記（ＩＩ）の乳化重合を２５℃未満の温度で行うことを特徴とする［１］から［７］のいずれか１つのオルガノポリシロキサンエマルション組成物の製造方法。
　［９］：前記（ＩＩ）の乳化重合における重合時間を４８時間以内とすることを特徴とする［１］から［８］のいずれか１つのオルガノポリシロキサンエマルション組成物の製造方法。
　［１０］：前記目的のエマルション組成物のエマルション粒子の平均粒径を５００ｎｍ以下とすることを特徴とする［１］から［９］のいずれか１つのオルガノポリシロキサンエマルション組成物の製造方法。
　［１１］：前記目的のエマルション組成物中のオルガノポリシロキサンに含まれるオクタメチルシクロテトラシロキサンの含有量を２，０００ｐｐｍ以下とすることを特徴とする［１］から［１０］のいずれか１つのオルガノポリシロキサンエマルション組成物の製造方法。 The present specification includes the following aspects.
[1]: (I) (A) an organopolysiloxane represented by the following general formula (1) and having an octamethylcyclotetrasiloxane content of 3,000 ppm or less: 100 parts by mass,

(In the formula, R ¹ 's are each independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and R ^2's are each independently a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms. n is a number that provides a viscosity of the organopolysiloxane at 25° C. of 15 mPa·s or more and 100,000 mPa·s or less.)
(B) an organoalkoxysilane represented by the following general formula (2), a partial hydrolysis condensate thereof, or a mixture thereof: 0.2 to 20 parts by mass,

(In the formula, each R ³ is independently a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, and each R ⁴ is independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms; and m is 3 to 4.)
(C) a nonionic surfactant: 2 to 30 parts by mass; and
(D-1) A mixture containing 1 to 10,000 parts by mass of water is emulsified to prepare a first emulsion composition;
(II) The first emulsion composition,
(D-2) Water: 0 to 10,000 parts by mass is added,
A method for producing an organopolysiloxane emulsion composition, comprising: carrying out emulsion polymerization in the presence of 0.1 to 20 parts by mass of an organic base catalyst (E) at a temperature of less than 40°C; producing an organopolysiloxane having a viscosity at 25°C of 300,000 mPa s or more, containing octamethylcyclotetrasiloxane in an amount of 3,000 ppm or less, and providing a target emulsion composition having an average emulsion particle size of 1 μm or less.
[2]: The method for producing an organopolysiloxane emulsion composition according to [1], characterized in using as component (A) an organopolysiloxane in which n in general formula (1) is a number that results in a viscosity of the organopolysiloxane at 25°C of 15 mPa s or more and 1,800 mPa s or less.
[3]: The method for producing an organopolysiloxane emulsion composition according to [1] or [2], characterized in that the content of component (B) is 0.4 to 10 parts by mass.
[4]: The method for producing an organopolysiloxane emulsion composition according to any one of [1] to [3], characterized in that the organic base catalyst (E) is at least one selected from the group consisting of tetramethylguanidine, diazabicycloundecene, diazabicyclononene, triazabicyclodecene, methyltriazabicyclodecene, and diazabicyclooctane.
[5]: The method for producing an organopolysiloxane emulsion composition according to any one of [1] to [4], wherein the organic base catalyst (E) is used in an amount of 0.5 to 7 parts by mass per 100 parts by mass of component (A).
[6]: The method for producing an organopolysiloxane emulsion composition according to any one of [1] to [5], characterized in that no anionic surfactant is used.
[7]:
The method for producing an organopolysiloxane emulsion composition according to any one of [1] to [6], wherein no cationic surfactant is used.
[8]: The method for producing an organopolysiloxane emulsion composition according to any one of [1] to [7], characterized in that the emulsion polymerization of (II) is carried out at a temperature of less than 25°C.
[9]: The method for producing an organopolysiloxane emulsion composition according to any one of [1] to [8], characterized in that the polymerization time in the emulsion polymerization of (II) is within 48 hours.
[10]: The method for producing an organopolysiloxane emulsion composition according to any one of [1] to [9], characterized in that the average particle size of the emulsion particles in the target emulsion composition is 500 nm or less.
[11]: The method for producing an organopolysiloxane emulsion composition according to any one of [1] to [10], characterized in that the content of octamethylcyclotetrasiloxane contained in the organopolysiloxane in the target emulsion composition is 2,000 ppm or less.

The present invention is not limited to the above-described embodiments. The above-described embodiments are merely examples, and anything that has substantially the same configuration as the technical idea described in the claims of the present invention and provides similar effects is included within the technical scope of the present invention.

Claims (11)

(I) (A) 100 parts by mass of an organopolysiloxane represented by the following general formula (1) and having an octamethylcyclotetrasiloxane content of 3,000 ppm or less:

(In the formula, R ¹ 's are each independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and R ^2's are each independently a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms. n is a number that provides a viscosity of the organopolysiloxane at 25° C. of 15 mPa·s or more and 100,000 mPa·s or less.)
(B) an organoalkoxysilane represented by the following general formula (2), a partial hydrolysis condensate thereof, or a mixture thereof: 0.2 to 20 parts by mass,

(In the formula, each R ³ is independently a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, and each R ⁴ is independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms; and m is 3 to 4.)
(C) a nonionic surfactant: 2 to 30 parts by mass; and
(D-1) A mixture containing 1 to 10,000 parts by mass of water is emulsified to prepare a first emulsion composition;
(II) The first emulsion composition,
(D-2) Water: 0 to 10,000 parts by mass is added,
A method for producing an organopolysiloxane emulsion composition, comprising: carrying out emulsion polymerization in the presence of 0.1 to 20 parts by mass of an organic base catalyst (E) at a temperature of less than 40°C; producing an organopolysiloxane having a viscosity at 25°C of 300,000 mPa s or more, containing octamethylcyclotetrasiloxane in an amount of 3,000 ppm or less, and having an average emulsion particle size of 1 μm or less. The method for producing an organopolysiloxane emulsion composition according to claim 1, characterized in that the organopolysiloxane used as component (A) is an organopolysiloxane in which n in the general formula (1) is a number that results in a viscosity of the organopolysiloxane at 25°C of 15 mPa·s or more and 1,800 mPa·s or less. The method for producing an organopolysiloxane emulsion composition according to claim 1, characterized in that the content of component (B) is 0.4 to 10 parts by mass. The method for producing an organopolysiloxane emulsion composition according to claim 1, characterized in that the (E) organic base catalyst is one or more selected from tetramethylguanidine, diazabicycloundecene, diazabicyclononene, triazabicyclodecene, methyltriazabicyclodecene, and diazabicyclooctane. The method for producing an organopolysiloxane emulsion composition according to claim 1, characterized in that 0.5 to 7 parts by mass of the (E) organic base catalyst is used per 100 parts by mass of component (A). The method for producing the organopolysiloxane emulsion composition according to claim 1, characterized in that no anionic surfactant is used. The method for producing the organopolysiloxane emulsion composition according to claim 1, characterized in that no cationic surfactant is used. The method for producing an organopolysiloxane emulsion composition according to claim 1, characterized in that the emulsion polymerization of (II) is carried out at a temperature of less than 25°C. The method for producing an organopolysiloxane emulsion composition according to claim 1, characterized in that the polymerization time in the emulsion polymerization of (II) is 48 hours or less. The method for producing an organopolysiloxane emulsion composition according to claim 1, characterized in that the average particle size of the emulsion particles of the target emulsion composition is 500 nm or less. The method for producing an organopolysiloxane emulsion composition according to any one of claims 1 to 10, characterized in that the content of octamethylcyclotetrasiloxane contained in the organopolysiloxane in the target emulsion composition is 2,000 ppm or less.