JPH0873748A - Aminated organopolysiloxane microemulsion and its production - Google Patents

Abstract

PURPOSE: To obtain a microemulsion excellent in storage stability and thermal stability and suitable for a fiber treatment, etc., by emulsifying a specific aminated organopolysiloxane, a surfactant, an acid, and water in the presence of a glycol ether. CONSTITUTION: A microemulsion comprising 100 pts.wt. aminated. organopolysiloxane of the formula [R<1> is II, a 1-20C monovalent hydrocarbon group, etc.; A is-R<2> (NR<3> R<4> )2 NR<5> R<6> (R<2> and R<4> are each a 1-6C divalent hydrocarbon group; R<3> , R<5> , and R<6> are each H or a 1-20C monovalent hydrocarbon group; and z is 0-5); and 0<x<=3 and 0<y<=3 provided 0<x+y<=3], 10-1,000 pts.wt. surfactant, 5-1,000 pts.wt. glycol ether, and 40-500,000 pts.wt. water is produced. In the production process, an acid, pref. having an optionally substd. amino group in the molecule, is added in an equivalent ratio of hydrogen ions in the acid to nitrogen atoms in the organopolysiloxane of 0.1 or higher to neutralize the emulsion.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to an amino group-containing organopolysiloxane microemulsion and a method for producing the same. More specifically, the present invention has excellent storage stability, dilution stability, mechanical stability, and thermal stability at high temperatures,
The present invention relates to an amino group-containing organopolysiloxane microemulsion which has a transparent appearance and can be suitably used as a fiber treatment agent and the like, and a method for producing the same.

[0002]

2. Description of the Related Art Conventionally, amino group-containing organopolysiloxane emulsions have been prepared by mixing liquid amino group-containing organopolysiloxane with a surfactant, for example, a homomixer,
It is produced by emulsifying and dispersing in water with a device capable of applying high shearing force such as a colloid mill or a stirring device such as a propeller blade. However, the amino group-containing organopolysiloxane emulsion produced by this conventional method has a large average particle size of 0.5 μm or more,
Poor storage stability, dilution stability, especially stability against mechanical shearing.For example, when used as a fiber treatment agent, when the processing speed is high, emulsion breakage occurs due to rolls rotating at high speed, resulting in uneven processing and stains on the rolls. There was a drawback that the problem of was likely to occur.

As a method for producing an amino group-containing organopolysiloxane emulsion, an emulsion polymerization method is also well known, in which a low molecular weight cyclic siloxane and aminosilane are used as starting materials, and a high alkali is used as a catalyst to polymerize and polymerize in an emulsion dispersion system. (Japanese Patent Publication No. 56-38609). According to this method, the average particle size of the obtained emulsion can be made as small as 0.1 to 0.2 μm, and the storage stability and dilution stability are considerably improved, but the stability against mechanical shearing is increased. Was still insufficient.

Further, an amino group-containing organopolysiloxane emulsion is prepared by adding a organopolysiloxane to a mixture of a surfactant soluble in water or a polyhydric alcohol and a polyhydric alcohol to obtain a precursor composition. It can also be manufactured (Japanese Patent Publication No. 4-49581). The composition in this method is translucent or transparent, and although the average particle size of the emulsion obtained by adding water to it is 0.5 μm or less, the storage stability, dilution stability and mechanical stability are insufficient. Met.

In addition to the above, as an amino group-containing organopolysiloxane microemulsion and a method for producing the same, a method of adding a surfactant and an acidic substance to the amino group-containing organopolysiloxane and heating the entire system to 50 ° C. or higher is known. (Japanese Patent Laid-Open No. 2-503204 and Japanese Patent Laid-Open No. 2-284959). However, the microemulsion produced by this method has an average particle size of 0.1 μm.
It is as small as the following, storage stability, dilution stability and mechanical stability are fairly good, but storage stability under high temperature conditions such as 50 to 90 ° C, thermal stability, mechanical stability, dilution stability , Transparency was insufficient.

[0006]

In view of such circumstances, the present invention has excellent storage stability, dilution stability, mechanical stability, and thermal stability at high temperatures, and has a transparent appearance. It is an object of the present invention to provide an amino group-containing organopolysiloxane microemulsion which can be suitably used as a fiber treating agent and a method for producing the same.

[0007]

Means for Solving the Problems As a result of various studies on methods for overcoming the drawbacks of the prior art, the present inventors have found that in addition to amino group-containing organopolysiloxane, surfactant, acid and water, glycol ether coexists. By emulsifying and emulsifying, a microemulsion with far superior storage stability, thermal stability, mechanical stability, dilution stability, and transparency can be obtained compared to the conventional microemulsion. The inventors have found the above and further studied to complete the present invention.

That is, the present invention has the following formula:

Embedded image {In the formula, R ¹ is a hydrogen atom, a hydroxyl group, a monovalent hydrocarbon group having 1 to 20 carbon atoms or the following formula: -OR '(wherein R 1
′ Represents a monovalent hydrocarbon group having 1 to 20 carbon atoms)
Represents a group represented by the formula: A is the following formula: -R ² (NR ³ R ⁴ ).
_z NR ⁵ R ⁶ (in the formula, R ² and R ⁴ each independently represent a divalent hydrocarbon group having 1 to 6 carbon atoms, R ³
R ⁵ and R ⁶ each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms, and z represents an integer of 0 to 5), and x and y have the following conditions: 0 <x ≦ 3, 0 ≦ y
<3, 0 <x + y ≦ 3, and the proportion of amino groups in the molecular weight of the compound of formula I is 0.25% by weight or more in terms of NH _2. } Containing 100 parts by weight of organopolysiloxane, 1 surfactant
0 to 1000 parts by weight, glycol ether 5 to 1000
In producing an emulsion composed of 40 parts by weight of water and 40 to 500000 parts by weight of water, an amount of acid equivalent to 0.1 chemical equivalent or more in terms of hydrogen ion with respect to the nitrogen atom in the amino group-containing organopolysiloxane molecule. The present invention relates to a method for producing an amino group-containing organopolysiloxane microemulsion, which comprises neutralizing and adding an amino group.

The amino group-containing organopolysiloxane used in the present invention is not particularly limited as long as it is represented by the above formula I. In the formula I, the group R ¹ is a hydrogen atom, a hydroxyl group, a monovalent hydrocarbon group having 1 to 20 carbon atoms, for example, an alkyl group such as a methyl group, an ethyl group, a propyl group, an octyl group, a lauryl group, a vinyl group or an allyl group. Alkenyl groups such as groups, phenyl groups, tolyl groups, aryl groups such as naphthyl groups, cyclopentyl groups, cycloalkyl groups such as cyclohexyl groups, or groups in which some or all of their hydrogen atoms are replaced with halogen atoms, or The following formula: -OR
′ ′ (Wherein R ′ represents a monovalent hydrocarbon group having 1 to 20 carbon atoms (for example, those exemplified for R ¹ ) ′).

The group A has the following formula: -R ² (NR ³ R ⁴ ).
_z NR ⁵ R ⁶ is an organic functional group, and R ² and R ⁴ are independently of each other a divalent hydrocarbon group having 1 to 6 carbon atoms, for example, methylene group, ethylene group, propylene group, hexamethylene. Group, phenylene group, etc., R ³ ,
R ⁵ and R ⁶ are each independently a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms (for example, those exemplified for R ¹ ) and z is an integer of 0 to 5. As the organic functional group _{A, -C 3 H 6 NH 2} , -C
_{3 H 6 NHC 2 H 4 NH} 2, -C 6 H 12 NHC 2 H 4 N
_{H 2, -C 3 H 6 (} NHC 2 H 4) 2 NH 2, -C 2 H
₄ NHC ₂ H ₄ NH ₂ , -C ₂ H ₄ NHC ₂ H ₄ N (C
H ₃ ) _{2 and the} like can be mentioned, but the present invention is not limited thereto.

Note that x and y in the above formula I are numbers satisfying the following conditions: 0 <x ≦ 3, 0 ≦ y <3, 0 <x + y ≦ 3.

Further, in the present invention, it is essential that the amino group in the amino group-containing organopolysiloxane molecule represented by the formula I is 0.25% by weight or more in terms of NH ₂ . The reason is that when the amount of amino groups is out of this range, the hydrophilicity of the amino group-containing organopolysiloxane is insufficient, and the transparency of the microemulsion produced is deteriorated.

As a typical specific example of the amino group-containing organopolysiloxane represented by the above formula I, the following formula:

[Chemical 3] Where R ¹ and A have the same meaning as defined for formula I, R ² has the meaning of R ¹ or A, m
Is 0 to 25,000, preferably 10 to 2000, more preferably 80 to 750, and n is in the same numerical range as m, but the ratio of amino groups in the molecule is 0.25 parts by weight or more in terms of NH _2. However, the present invention is not limited to this, and an amino group-containing organopolysiloxane having a branched structure can also be used. Further, the amino group-containing organopolysiloxane of the formula I is generally one in which the end of the polysiloxane chain is blocked with a trialkylsilyl group such as a trimethylsilyl group, but a part or all of the alkyl group is a hydroxyl group or an alkoxy group. It may be blocked with a trialkylsilyl group substituted with a group or an amino group-containing group.

The surfactant used in the present invention is
Various conventionally known substances such as nonionic surfactants, anionic surfactants, cationic surfactants, zwitterionic surfactants, and silicone surfactants can be used. Specific examples of the surfactant include nonionic surfactants such as polyoxyethylene alkylphenyl ether, polyoxyethylene alkyl ether, polyoxyethylene alkyl ester, sorbitan fatty acid ester or sucrose fatty acid ester, and anionic surfactants. Agents such as alkyl sulfates, alkylphenyl sulfonates or polyoxyethylene alkylphenyl sulfates, cationic surfactants such as alkyltrimethylammonium chloride, dialkyldimethylammonium chloride, benzyltrimethylammonium chloride, zwitterionic surfactants, etc. Agents, such as alkyl betaines or alkyl amino acids, may be used, and one or more of them may be used, but among them, combination with other ionic components HL terms of the non-ionic preferably the use of surfactants, in particular surfactants used
It is preferable to select the total B (hydrophilic group / lipophilic group balance) value to be 8 to 15.

The amount of the above surfactant added is 10 to 1 with respect to 100 parts by weight of the amino group-containing organopolysiloxane.
000 parts by weight, preferably 10 to 100 parts by weight.
If the amount of the surfactant added is less than 10 parts by weight, a transparent microemulsion cannot be obtained, and the stability of the microemulsion increases as the amount added increases. However, when the amount of the surfactant exceeds 1000 parts by weight, the characteristics of the amino group-containing organopolysiloxane are impaired, and when the resulting microemulsion is used as a fiber treating agent, for example,
There arises such an adverse effect that the unique texture of the amino group-containing organopolysiloxane cannot be obtained.

The glycol ether used in the present invention improves the storage stability, dilution stability, mechanical stability, thermal stability, transparency, usability, etc. of the amino group-containing organopolysiloxane microemulsion. The type is not particularly limited, but is preferably a glycol ether that dissolves in water at 25 ° C. at an arbitrary ratio, and specific examples include ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, and triethylene glycol monomethyl. Ether, propylene glycol monomethyl ether,
Dipropylene glycol monomethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monopropyl ether, diethylene glycol monopropyl ether, propylene glycol monopropyl ether, diethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monoisobutyl ether, diethylene glycol monobutyl ether, triethylene Examples thereof include glycol monobutyl ether and ethylene glycol monoisobutyl ether, and these may be used alone or in combination of two or more kinds. Further, when the amino group-containing organopolysiloxane microemulsion of the present invention is used as a fiber treating agent, if one of these glycol ethers having a relatively small molecular weight and a boiling point of 300 ° C. or less is used, the fiber after the fiber treatment is treated. Since no glycol ether remains on the top, the characteristics of the amino group-containing organopolysiloxane are sufficiently exhibited, which is preferable.

If the amount of glycol ether added is too small, the effect due to the addition is insufficient. Even if the amount added is too large, the effect reaches saturation and does not increase any further, which is economically undesirable. . for these reasons,
The glycol ether is used in an amount of 5 to 1000 parts by weight, preferably 10 to 100 parts by weight, based on 100 parts by weight of the amino group-containing organopolysiloxane.

The acid used in the present invention is not particularly limited, and conventionally known acids can be used. For example, hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, lauric acid,
Stearic acid, glutamic acid, aspartic acid, oxyglutamic acid, etc. are mentioned, and these acids are 1 type or 2 types.
More than one species may be used. Particularly preferred acids are acids containing an amino group or a substituted amino group in the molecule, such as glutamic acid, aspartic acid and oxyglutamic acid.
When an acid containing an amino group or a substituted amino group is used in these molecules, the storage stability, dilution stability, and mechanical stability of the amino group-containing organopolysiloxane microemulsion are greater than when other acids are used. The heat resistance, thermal stability and transparency can be further improved. The above-mentioned preferred acid is originally low in metal corrosiveness and low in volatility,
For example, in the fiber processing step, corrosion or rust due to acid is unlikely to occur on the metal surface inside the piping, the processing device, the storage device, and the used device.

The amount of the above acid added is an amount equivalent to 0.1 chemical equivalent or more in terms of hydrogen ion with respect to the nitrogen atom in the amino group-containing organopolysiloxane molecule. here,
When the acid to be added is an acid having a basic group such as an amino group in the molecule, the difference between the valence of the acid and the valence of the base is defined as the effective valence of the acid. For example, glutamic acid is a monovalent acid because it has two carboxyl groups which are monovalent acids and one amino group which is a monovalent base in the molecule. By the addition of an acid, the amino group in the amino group-containing organopolysiloxane reacts with hydrogen ions to form an amine salt, whereby the hydrophilicity of the amino group-containing organopolysiloxane is increased and a microemulsion can be obtained. Therefore, if the amount of the acid added is smaller than the above amount, the amino group-containing organopolysiloxane is insufficient in hydrophilicity, resulting in a cloudy emulsion. Further, the upper limit of the amount of the acid added is not particularly limited, but usually, it is not used in excess of 1 chemical equivalent in terms of hydrogen ion.

In the amino group-containing organopolysiloxane microemulsion of the present invention, other additives such as silane compounds, crosslinking agents, preservatives, salts and dimethylpolysiloxane, epoxy group-containing organopolysiloxane, carboxy group-containing organopolysiloxane are contained. Various polysiloxanes such as siloxanes, polysiloxane / polyoxyalkylene copolymers, silanol group-containing organopolysiloxanes and the like can be contained within a range not impairing the effects of the present invention.

In the present invention, the method of emulsifying and dispersing the amino group-containing organopolysiloxane in water is not particularly limited. For example, an amino group-containing organopolysiloxane, a surfactant, a glycol ether, water and optionally other additives may be added. The mixing and homogenization is performed by a stirring device such as a propeller blade or a homomixer. In addition, the neutralization method is not particularly limited, and for example, a method of stirring the acid as it is after the emulsification or adding an aqueous solution of the acid, an amino group-containing organopolysiloxane, a surfactant, a glycol ether and optionally other additions Examples include a method of dropping an aqueous solution of an acid into a mixture of agents to simultaneously emulsify and neutralize. Here, water is added alone or in the form of an aqueous solution of an acid, but since a microemulsion is formed, the final addition amount of water is 40 to 500000 with respect to 100 parts by weight of the amino group-containing organopolysiloxane. It is appropriately selected from the range of parts by weight.

[0022]

EXAMPLES Next, the present invention will be described in more detail based on examples, but the present invention is not limited to these examples, and those embodying the technical idea of the present invention are within the scope of the present invention. Contained within. Example 1 The following formula:

[Chemical 4] The amino group-containing organopolysiloxane 120 represented by
g, polyoxyethylene lauryl ether {ethylene oxide (EO) addition mole number 8 moles, HLB = 13.1}
60 g of ethylene glycol monoisopropyl ether and 20 g of ethylene glycol monoisopropyl ether were charged into a beaker of 1 liter and uniformly mixed for 5 minutes at 3000 rpm with a homomixer, and then, under the same stirring, 700 g of water was added to 8.8 g of L-glutamic acid (amino group-containing organopolysiloxane). An aqueous solution in which 0.4 equivalent of hydrogen ion equivalent to nitrogen atoms in the molecule was dissolved was added and stirred for 10 minutes to obtain a microemulsion. This is called microemulsion A.

Example 2 Aside from using L-glutamic acid, 1.8 g of acetic acid (corresponding to 0.2 chemical equivalent in terms of hydrogen ion to nitrogen atom in amino group-containing organopolysiloxane molecule) was used as the acid. A microemulsion was obtained in the same manner as in Example 1. This is called microemulsion B.

Example 3 Instead of ethylene glycol monoisopropyl ether,
A microemulsion was obtained in the same manner as in Example 1 except that 20 g of triethylene glycol monobutyl ether was used. This is called microemulsion C.

Example 4 To 800 g of the microemulsion A obtained in Example 1, 1.0 of γ-glycidoxypropyltrimethoxysilane was added.
g was added and completely dissolved by stirring. This is called microemulsion D.

Example 5 The following formula:

[Chemical 5] The amino group-containing organopolysiloxane 120 represented by
g, polyoxyethylene nonyl phenyl ether (EO
Addition number of moles: 7 moles, HLB = 11.6), 60 g, and dipropylene glycol monomethyl ether, 30 g are charged into a 1-liter beaker, and 3000 rpm with a homomixer.
After uniformly mixing for 5 minutes at 550 g with water under the same stirring.
An aqueous solution in which 5.2 g of aspartic acid (corresponding to 0.5 chemical equivalent in terms of hydrogen ion with respect to nitrogen atom in amino group-containing organopolysiloxane molecule) was dissolved was added,
The mixture was stirred for 10 minutes to obtain a microemulsion. This is called microemulsion E.

Example 6 Example 4 was carried out except that 1.4 g of formic acid (corresponding to 0.4 chemical equivalent in terms of hydrogen ion relative to nitrogen atom in amino group-containing organopolysiloxane molecule) was used as an acid instead of aspartic acid. A microemulsion was obtained in the same manner as in Example 5. This is called microemulsion F.

Example 7 A microemulsion was obtained in the same manner as in Example 5 except that 20 g of ethylene glycol monomethyl ether was used instead of dipropylene glycol monomethyl ether. This is called microemulsion G.

Example 8 To 800 g of the microemulsion E obtained in Example 5, {N-β- (aminoethyl) -γ-aminopropyl}
-Trimethoxysilane 0.4g was added and completely dissolved by stirring. This is called microemulsion H.

Example 9 The following formula:

[Chemical 6] The amino group-containing organopolysiloxane 150 represented by
g, 60 g of polyoxyethylene tridecyl ether (10 moles of EO addition mole number, HLB = 13.7), and 50 g of dipropylene glycol monopropyl ether were charged in a beaker of 1 liter, and 3000 rpm with a homomixer.
After homogeneously mixing for 5 minutes, 700 g of water under the same stirring
An aqueous solution in which 3.9 g of sulfamic acid (corresponding to 0.1 chemical equivalent in terms of hydrogen ion to nitrogen atom in amino group-containing organopolysiloxane molecule) was dissolved was added,
The mixture was stirred for 10 minutes to obtain a microemulsion. This is called Micro Emulsion I.

Comparative Example 1 A microemulsion was produced in the same manner as in Example 2 except that ethylene glycol monoisopropyl ether was not used. This is called Micro Emulsion J.

Comparative Example 2 A microemulsion was produced in the same manner as in Example 6 except that dipropylene glycol monomethyl ether was not used. This is called microemulsion K.

Comparative Example 3 A microemulsion was prepared in the same manner as in Example 9 except that propylene glycol monopropyl ether was not used. This is called microemulsion L.

Comparative Example 4 Comparative Example 1 except that the acid was changed to 6.3 g of 35% hydrochloric acid (corresponding to 0.4 chemical equivalent in terms of hydrogen ion with respect to nitrogen atom in amino group-containing organopolysiloxane molecule). A microemulsion was prepared in a similar manner. This is called microemulsion M.

Comparative Example 5 The same as Comparative Example 2 except that the acid was 2.3 g of acetic acid (corresponding to 0.5 chemical equivalent in terms of hydrogen ion with respect to nitrogen atom in amino group-containing organopolysiloxane molecule). The method produced a microemulsion. This is called Micro Emulsion N.

Comparative Example 6 The same as Comparative Example 3 except that the acid was 3.0 g of propionic acid (equivalent to 0.1 chemical equivalent in terms of hydrogen ion to nitrogen atom in amino group-containing organopolysiloxane molecule). A microemulsion was produced by the method described in 1. This is called microemulsion O.

Comparative Example 7 A microemulsion was produced in the same manner as in Example 2 except that glycerin was used instead of ethylene glycol monoisopropyl ether. This is called microemulsion P.

Comparative Example 8 A microemulsion was produced in the same manner as in Example 6 except that ethylene glycol was used instead of dipropylene glycol monomethyl ether. This is called microemulsion Q.

Regarding the microemulsions A to I and J to Q obtained in Examples 1 to 9 and Comparative Examples 1 to 8,
Transparency, storage stability (50 ℃, 70 ℃), mechanical stability,
The dilution stability was evaluated. The results are shown in Tables 1 and 2. The evaluation method and criteria of each characteristic are as follows.

Evaluation method Transparency: Visual observation of the appearance of the microemulsion immediately after production. Storage stability (50 ° C, 30 days): 100 g of the microemulsion was placed in a 200 ml sealed glass bottle, and 5
Let stand in a constant temperature bath at 0 ° C and visually observe the appearance after 30 days. Storage stability (70 ° C, 7 days): 100 g of the microemulsion was placed in a 200 ml sealed glass bottle, and 70
Let stand in a constant temperature bath at ℃ and visually observe the appearance after 7 days. Mechanical stability: The microemulsion was diluted to 2% with water, stirred with a homomixer at 8000 rpm for 10 minutes, and then visually observed. Dilution stability (50 ° C, 7 days): Dilute the microemulsion to 2% with water, put it in a 200 ml sealed glass bottle, leave it in a constant temperature bath at 50 ° C, and visually observe the appearance after 7 days. .

Evaluation Criteria ⊚: A colorless and transparent appearance (light transmittance 80 to 10)
0T%) O: Appearance that is pale white and slightly turbid (light transmittance of 50 to 80)
T%) Δ: Appearance slightly clouded (light transmittance 20 to 50 T%) ×: White appearance (light transmittance 0 to 20 T%) or separation is observed

[0042]

[Table 1]

[0043]

From the above results, in the production of the amino group-containing organopolysiloxane microemulsion, in the present invention, a technique using a glycol ether, preferably a glycol ether soluble at 25 ° C. in water at an arbitrary ratio, and an acid are used. , Preferably in combination with the technique of using an acid containing an amino group or a substituted amino group in the molecule, as compared with the amino group-containing organopolysiloxane microemulsion obtained by the conventional method, storage stability, dilution stability, It was confirmed that an amino group-containing organopolysiloxane microemulsion having far superior performances in mechanical stability, thermal stability and transparency was obtained. In particular, the microemulsion of the present invention has outstanding storage stability and dilution stability at high temperatures.

[0045]

As described in detail above, the amino group-containing organopolysiloxane microemulsion obtained according to the present invention is higher than that produced by the conventional method, especially under high temperature conditions of 50 to 90 ° C. It has excellent storage stability, dilution stability, mechanical stability, thermal stability, and transparency. Therefore, the amino group-containing organopolysiloxane microemulsion of the present invention is particularly useful as a fiber treating agent and the like.

Claims (5)

[Claims] 1. The following formula I: {In the formula, R ¹ is a hydrogen atom, a hydroxyl group, a monovalent hydrocarbon group having 1 to 20 carbon atoms or the following formula: -OR '(wherein R 1
′ Represents a monovalent hydrocarbon group having 1 to 20 carbon atoms)
In represents a group represented by, A is the following ^{formula: -R 2 (NR 3 R 4} ) z NR 5 R 6 ( wherein,
R ² and R ⁴ independently of each other have 1 to 6 carbon atoms.
Represents a divalent hydrocarbon group, R ³ , R ⁵ and R ⁶ independently of each other represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms, and z represents an integer of 0 to 5 ) Represents an organic functional group, and x and y represent a number satisfying the following conditions: 0 <x ≦ 3, 0 ≦ y <3, 0 <x + y ≦ 3, and a compound represented by formula I The ratio of amino groups in the molecular weight of 0.25% by weight or more in terms of NH ₂ }, and 100 parts by weight of the amino group-containing organopolysiloxane represented by
When an emulsion consisting of 10 to 1000 parts by weight of a surfactant, 5 to 1000 parts by weight of glycol ether, and 40 to 500000 parts by weight of water is produced, hydrogen ions are added to nitrogen atoms in the amino group-containing organopolysiloxane molecule. A method for producing an amino group-containing organopolysiloxane microemulsion, which comprises neutralizing by adding an amount of acid equivalent to 0.1 chemical equivalent or more. 2. The production method according to claim 1, wherein an acid having an amino group or a substituted amino group in the molecule is used as the acid. 3. The method according to claim 1, wherein one or both of glutamic acid and aspartic acid are used as the acid. 4. The production method according to claim 1, wherein a glycol ether which is soluble in water at 25 ° C. at an arbitrary ratio is used as the glycol ether. 5. An amino group-containing organopolysiloxane microemulsion produced by the method according to any one of claims 1 to 4.