JP2013234157A - Silicone-modified zwitterionic compound and method for producing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a new silicone-modified zwitterionic compound with high solubility and a low melting point, and to provide a method for producing the same.SOLUTION: A silicone-modified zwitterionic compound is provided, being represented by formula (1) [wherein, at least one of R, Rand Rhas a structure of formula (2), others are any of 1-6C alkyl, aryl, fluorine-substituted alkyl and hydroxyl-containing alkyl, and two of R, Rand Rmay form a ring; l is an integer of 3-6 (in formula (2), Ris 1-8C organic group or siloxane linkage-bearing group; R, Rand Rare any of 1-8C monovalent organic group, siloxane-linkage-bearing group and a siloxy group represented by -OSiRRR; m is 1-4; n is 1-10; and (a) is an integer of 0-2)].

Description

  The present invention relates to a silicone-modified zwitterionic compound and a method for producing the same.

  An ionic liquid is a salt composed of a cation such as imidazolium, pyridinium, quaternary ammonium or quaternary phosphonium and an anion such as halogen, triflate, tetrafluoroborate or hexafluorophosphate at a relatively low temperature. It takes a liquid state (see, for example, Patent Document 1). The characteristics of these ionic liquids include low vapor pressure, almost no flammability, high thermal stability, and ionic conductivity. These ionic compounds have been studied for introduction as electrolyte solutions or as additives to electrolytes in electrochemical devices such as lithium batteries, electric double layer capacitors, electrolytic capacitors, electrochromic devices, and dye-sensitized solar cells. Yes. Furthermore, it is a compound expected to be introduced into various fields such as surfactants, gelling agents, antistatic agents, catalysts and antibacterial agents.

  In addition, a zwitterionic compound having a cation moiety and an anion moiety in the same molecule has also been developed (see, for example, Patent Document 2). The conventional ionic compound is a compound composed of a cation molecule and an anion molecule. When a specific ion such as a battery is moved, for example, only a lithium cation or a proton, the cation and anion of the ionic compound also move, This will cause a decrease in the transport rate of the target ions. A zwitterionic compound having a cation and an anion in the same molecule has been developed to suppress the movement (see, for example, Non-Patent Document 1). However, conventional zwitterionic compounds having a cation and an anion in the same molecule are limited in the degree of freedom of ions of the cation and anion. Because of their high melting point and high polarity, these zwitterionic compounds were soluble only in protic solvents such as water and ethanol. Therefore, development of a novel zwitterionic compound that has a lower melting point and is soluble in other organic solvents has been eagerly desired.

Japanese National Patent Publication No. 8-509242 JP 2005-272316 A

Supervised by Hiroyuki Ohno “Development and Prospects of Ionic Liquids” CM Publishing 2008

  The present invention has been made in view of the above circumstances, and an object thereof is to provide a novel silicone-modified zwitterionic compound having high solubility in various organic solvents and having a melting point in the range of 70 to 200 ° C. and a method for producing the same. And

［式中Ｒ^１、Ｒ^２、Ｒ^３は、同一でも異なっていてもよい炭素数１から６のアルキル基、アリール基、フッ素置換アルキル基、水酸基含有ヒドロキシアルキル基、及び下記式（２）で表されるウレタン結合を有するオルガノポリシロキサン構造のいずれかを示し、Ｒ^１、Ｒ^２、Ｒ^３のうち２つは環を形成してもよく、その場合はアルキレン基を表わす。Ｒ^１、Ｒ^２、Ｒ^３のうち少なくとも１つは下記式（２）の構造を示す。ｌは３から６の整数である。

（式中Ｒ^４は炭素数１から８の１価の有機基またはシロキサン結合を有する基であり、Ｒ^５、Ｒ^６、Ｒ^７は各々炭素数１から８の１価の有機基、シロキサン結合を有する基、及び
−ＯＳｉＲ^８Ｒ^９Ｒ^１０で示されるシロキシ基（Ｒ^８、Ｒ^９、Ｒ^１０は各々炭素数１から８の１価の有機基）のいずれかである。ｍは１から４の整数、ｎは１から１０の整数、ａは０から２の整数である。）］ The present invention has been made to solve the above problems, and is a silicone-modified bifunctional compound having a quaternary ammonium ion cation moiety and a sulfonate ion anion moiety represented by the following formula (1). Zwitterionic compounds are provided.

[Wherein R ¹ , R ² and R ³ may be the same or different and each represents an alkyl group having 1 to 6 carbon atoms, an aryl group, a fluorine-substituted alkyl group, a hydroxyl group-containing hydroxyalkyl group, and the following formula (2): One of the organopolysiloxane structures having a urethane bond represented is shown, and ^{two of} R ¹ , R ² and R ³ may form a ring, in which case an alkylene group is represented. At least one of R ¹ , R ² and R ³ has the structure of the following formula (2). l is an integer of 3 to 6.

(In the formula, R ⁴ is a monovalent organic group having 1 to 8 carbon atoms or a group having a siloxane bond, and R ⁵ , R ⁶ and R ⁷ are each a monovalent organic group having 1 to 8 carbon atoms and a siloxane bond. And a siloxy group represented by -OSiR ⁸ R ⁹ R ¹⁰ (R ⁸ , R ⁹ and R ¹⁰ are each a monovalent organic group having 1 to 8 carbon atoms), m is 1 4 is an integer, n is an integer from 1 to 10, and a is an integer from 0 to 2.)]

  Such a silicone-modified zwitterionic compound is obtained by silicone-modifying a zwitterionic compound in which a cation and an anion are present in the same molecule, and has a melting point lower than that of the conventional zwitterionic compound and is 70 to 200 ° C. It is characterized by not only melting in a temperature range of <RTIgt;, </ RTI> but becoming a liquid state, being hardly decomposed to around 250-300 [deg.] C., and having high solubility in various organic solvents. For this reason, for example, such a silicone-modified zwitterionic compound can be dissolved by heating as an antistatic agent and kneaded into a resin or the like, or dissolved in a solvent and mixed into the composition.

In this case, in the above formula (2), it is preferable that n is 3, R ⁵ , R ⁶ and R ⁷ are methyl groups and a is 0.

  Such a silicone-modified zwitterionic compound has a lower melting point than conventional zwitterionic compounds, and is much more soluble in various organic solvents.

  Further, the silicone-modified zwitterionic compound includes a conductive salt or additive in an electrolyte for an electrochemical or electro-optic cell, a conductive salt or additive in a battery electrolyte, or a conductive salt or additive in an electrolyte of a lithium secondary battery. It can be suitably used for agents, antistatic agents, surfactants, foaming agents and the like.

  The silicone-modified zwitterionic compound of the present invention has a lower melting point than conventional zwitterionic compounds and melts in a temperature range of 70 to 200 ° C. to become a liquid state, but also decomposes to around 250 to 300 ° C. It is difficult to perform and is highly soluble in various organic solvents. For this reason, it is beneficial to use it more suitably for conductive salts or additives, antistatic agents, surfactants, foaming agents and the like.

  The silicone-modified zwitterionic compound can also be suitably used for double layer capacitors, super capacitors, lithium capacitors, and the like.

  The silicone-modified zwitterionic compound of the present invention has a lower melting point than conventional zwitterionic compounds and melts in a temperature range of 70 to 200 ° C. to become a liquid state, but also decomposes to around 250 to 300 ° C. Since it has the effect of being highly soluble in various organic solvents, it can be suitably used for the capacitor and the like.

［式中Ｒ^１、Ｒ^２、Ｒ^３は、同一でも異なっていてもよい炭素数１から６のアルキル基、アリール基、及びフッ素置換アルキル基、水酸基含有ヒドロキシアルキル基、及び下記式（２）で表されるウレタン結合を有するオルガノポリシロキサン構造のいずれかを示し、Ｒ^１、Ｒ^２、Ｒ^３のうち２つは環を形成してもよく、その場合はアルキレン基を表わす。Ｒ^１、Ｒ^２、Ｒ^３のうち少なくとも１つは下記式（２）の構造を示す。ｌは３から６の整数である。

（式中Ｒ^４は炭素数１から８の１価の有機基またはシロキサン結合を有する基、Ｒ^５、Ｒ^６、Ｒ^７は各々炭素数１から８の１価の有機基、シロキサン結合を有する基、及び−ＯＳｉＲ^８Ｒ^９Ｒ^１０で示されるシロキシ基（Ｒ^８、Ｒ^９、Ｒ^１０は各々炭素数１から８の１価の有機基）のいずれかである。ｍは１から４の整数、ｎは１から１０の整数、ａは０から２の整数である。］

（式中Ｒ^１、Ｒ^２、Ｒ^３は上記と同様である。） In the present invention, a silicone-modified zwitterionic compound represented by the following formula (1) is produced by reacting a silicone-modified tertiary amine represented by the following formula (3) with an alkyl sultone. A method for producing a silicone-modified zwitterionic compound is provided.

[Wherein R ¹ , R ² and R ³ may be the same or different and each has an alkyl group having 1 to 6 carbon atoms, an aryl group, a fluorine-substituted alkyl group, a hydroxyl group-containing hydroxyalkyl group, and the following formula (2): Any one of R ¹ , R ² , and R ³ may form a ring, and in this case, represents an alkylene group. At least one of R ¹ , R ² and R ³ has the structure of the following formula (2). l is an integer of 3 to 6.

(Wherein R ⁴ is a monovalent organic group having 1 to 8 carbon atoms or a group having a siloxane bond, and R ⁵ , R ⁶ and R ⁷ each have a monovalent organic group having 1 to 8 carbon atoms and a siloxane bond. And a siloxy group represented by —OSiR ⁸ R ⁹ R ¹⁰ (R ⁸ , R ⁹ and R ¹⁰ are each a monovalent organic group having 1 to 8 carbon atoms), m is 1 to 4; An integer, n is an integer from 1 to 10, and a is an integer from 0 to 2.]

(Wherein R ¹ , R ² and R ³ are the same as above)

  With such a method for producing a silicone-modified zwitterionic compound, it is possible to produce a silicone-modified zwitterionic compound having a lower melting point than conventional zwitterionic compounds and high solubility in various organic solvents. It is.

［式（４）中、Ｒ^４、Ｒ^５、Ｒ^６、Ｒ^７、−ＯＳｉＲ^８Ｒ^９Ｒ^１０、ｎ、ａは上記と同様である。］ In this case, the silicone-modified tertiary amine is obtained by reacting a hydroxyalkyl tertiary amine having at least one hydroxyl group with an organopolysiloxane having an isocyanate group represented by the following formula (4). It is preferable to use a tertiary amine.

[In the formula (4), R ⁴ , R ⁵ , R ⁶ , R ⁷ , —OSiR ⁸ R ⁹ R ¹⁰ , n and a are the same as above. ]

  Thus, the silicone-modified tertiary amine reacts with the hydroxyl group of the hydroxyalkyl tertiary amine having a hydroxyl group and the isocyanate group of the organopolysiloxane having an isocyanate group represented by the above formula (4) to form a urethane bond. It can be obtained by reaction.

  In this case, it is preferable to use tristrimethylsiloxysilylpropyl isocyanate (hereinafter abbreviated as “TMSI”) as the organopolysiloxane having an isocyanate group.

  Thus, it is particularly preferable to use TMSI as the organopolysiloxane having an isocyanate group. In this case, tristrimethylsiloxysilylpropylamine can be obtained as the silicone-modified tertiary amine.

Since the silicone-modified zwitterionic compound of the present invention has a siloxy group as shown in the above formula (1), the melting point is lower than that of the conventional zwitterionic compound, and N ⁺ and SO ³⁻ are present in the molecule. Therefore, it melts in a temperature range of 70 to 200 ° C. and becomes a liquid state, and is not easily decomposed to around 250 to 300 ° C., and has high solubility in various organic solvents. . For this reason, for example, it can be dissolved by heating as an antistatic agent and kneaded into a resin or the like, or dissolved in a solvent and mixed into the composition.

  Conventional zwitterionic compounds have a high melting point and are soluble only in protic solvents. As a result of intensive studies on the problem, the present inventors have found that the novel silicone-modified zwitterionic compound of the present invention has a low melting point and is soluble in other organic solvents. Was completed.

  Hereinafter, the silicone-modified zwitterionic compound of the present invention, the production method thereof, and the silicone-modified tertiary amine that is a material substance of the silicone-modified zwitterionic compound will be described in detail, but the present invention is not limited thereto. is not.

［式中Ｒ^１、Ｒ^２、Ｒ^３は、同一でも異なっていてもよい炭素数１から６のアルキル基、アリール基、フッ素置換アルキル基、水酸基含有ヒドロキシアルキル基、及び下記式（２）で表されるウレタン結合を有するオルガノポリシロキサン構造のいずれかを示し、Ｒ^１、Ｒ^２、Ｒ^３のうち２つは環を形成してもよく、その場合はアルキレン基を表わす。Ｒ^１、Ｒ^２、Ｒ^３のうち少なくとも１つは下記式（２）の構造を示す。ｌは３から６の整数である。

（式中Ｒ^４は炭素数１から８の１価の有機基またはシロキサン結合を有する基であり、Ｒ^５、Ｒ^６、Ｒ^７は各々炭素数１から８の１価の有機基、シロキサン結合を有する基、及び−ＯＳｉＲ^８Ｒ^９Ｒ^１０で示されるシロキシ基（Ｒ^８、Ｒ^９、Ｒ^１０は各々炭素数１から８の１価の有機基）のいずれかである。ｍは１から４の整数、ｎは１から１０の整数、ａは０から２の整数である。）］ The present invention is a silicone-modified zwitterionic compound represented by the following formula (1) having a quaternary ammonium ion cation moiety and a sulfonate ion anion moiety in the same molecule.

[Wherein R ¹ , R ² and R ³ may be the same or different and each represents an alkyl group having 1 to 6 carbon atoms, an aryl group, a fluorine-substituted alkyl group, a hydroxyl group-containing hydroxyalkyl group, and the following formula (2): One of the organopolysiloxane structures having a urethane bond represented is shown, and ^{two of} R ¹ , R ² and R ³ may form a ring, in which case an alkylene group is represented. At least one of R ¹ , R ² and R ³ has the structure of the following formula (2). l is an integer of 3 to 6.

(In the formula, R ⁴ is a monovalent organic group having 1 to 8 carbon atoms or a group having a siloxane bond, and R ⁵ , R ⁶ and R ⁷ are each a monovalent organic group having 1 to 8 carbon atoms and a siloxane bond. And a siloxy group represented by -OSiR ⁸ R ⁹ R ¹⁰ (R ⁸ , R ⁹ and R ¹⁰ are each a monovalent organic group having 1 to 8 carbon atoms), m is 1 4 is an integer, n is an integer from 1 to 10, and a is an integer from 0 to 2.)]

Such a silicone-modified zwitterionic compound of the present invention is a silicone-modified zwitterionic compound comprising a siloxy group, a urethane bond, N ⁺ and SO ^{3− in the} molecule, and the cation and anion are the same. By modifying the zwitterionic compound present in the molecule with silicone, it is highly soluble in various organic solvents, has a melting point in the range of 70 to 200 ° C., and is soluble in organic solvents other than protic solvents. is there.

（式中、Ｍｅはメチル基、Ｂｕはブチル基を示す。） Specific examples of the formula (1) include the following compounds.

(In the formula, Me represents a methyl group, and Bu represents a butyl group.)

In the formula (2), it is preferable that n is 3, R ⁵ , R ⁶ and R ⁷ are methyl groups and a is 0.

  The silicone-modified zwitterionic compound of the present invention includes a conductive salt or additive in an electrolyte for an electrochemical or electro-optic cell, a conductive salt or additive in a battery electrolyte, or a conductive salt or additive in an electrolyte of a lithium secondary battery. It can be suitably used for agents, antistatic agents, surfactants, foaming agents and the like.

  Moreover, it can be used suitably also for a double layer capacitor, a super capacitor, a lithium capacitor, or the like.

［式中Ｒ^１、Ｒ^２、Ｒ^３は、同一でも異なっていてもよい炭素数１から６のアルキル基、アリール基、及びフッ素置換アルキル基、水酸基含有ヒドロキシアルキル基、及び下記式（２）で表されるウレタン結合を有するオルガノポリシロキサン構造のいずれかを示し、Ｒ^１、Ｒ^２、Ｒ^３のうち２つは環を形成してもよく、その場合はアルキレン基を表わす。Ｒ^１、Ｒ^２、Ｒ^３のうち少なくとも１つは下記式（２）の構造を示す。ｌは３から６の整数である。

（式中Ｒ^４は炭素数１から８の１価の有機基またはシロキサン結合を有する基、Ｒ^５、Ｒ^６、Ｒ^７は各々炭素数１から８の１価の有機基、シロキサン結合を有する基、及び−ＯＳｉＲ^８Ｒ^９Ｒ^１０で示されるシロキシ基（Ｒ^８、Ｒ^９、Ｒ^１０は各々炭素数１から８の１価の有機基）のいずれかである。ｍは１から４の整数、ｎは１から１０の整数、ａは０から２の整数である。］

（式中Ｒ^１、Ｒ^２、Ｒ^３は上記と同様である。） In the present invention, a silicone-modified zwitterionic compound represented by the following formula (1) is produced by reacting a silicone-modified tertiary amine represented by the following formula (3) with an alkyl sultone. A method for producing a silicone-modified zwitterionic compound is provided.

[Wherein R ¹ , R ² and R ³ may be the same or different and each has an alkyl group having 1 to 6 carbon atoms, an aryl group, a fluorine-substituted alkyl group, a hydroxyl group-containing hydroxyalkyl group, and the following formula (2): Any one of R ¹ , R ² , and R ³ may form a ring, and in this case, represents an alkylene group. At least one of R ¹ , R ² and R ³ has the structure of the following formula (2). l is an integer of 3 to 6.

(Wherein R ⁴ is a monovalent organic group having 1 to 8 carbon atoms or a group having a siloxane bond, and R ⁵ , R ⁶ and R ⁷ each have a monovalent organic group having 1 to 8 carbon atoms and a siloxane bond. And a siloxy group represented by —OSiR ⁸ R ⁹ R ¹⁰ (R ⁸ , R ⁹ and R ¹⁰ are each a monovalent organic group having 1 to 8 carbon atoms), m is 1 to 4; An integer, n is an integer from 1 to 10, and a is an integer from 0 to 2.]

(Wherein R ¹ , R ² and R ³ are the same as above)

  The silicone-modified zwitterionic compound of formula (1) can be produced by reacting a silicone-modified tertiary amine and an alkyl sultone as described above.

  As a specific method for producing the silicone-modified zwitterionic compound of formula (1), a solution obtained by dissolving 0.1 mol of alkyl sultone in an organic solvent such as toluene is charged into a reaction vessel, and the silicone represented by formula (3) is prepared. A modified tertiary amine (0.1 mol) is dropped with stirring in a water bath, and a white solid is precipitated by stirring overnight. The target compound can be obtained by filtering it and washing with toluene and acetone.

  Specific examples of the alkyl sultone include 1,3-butane sultone and 1,4-propane sultone.

（式（４）中、Ｒ^４、Ｒ^５、Ｒ^６、Ｒ^７、−ＯＳｉＲ^８Ｒ^９Ｒ^１０、ｎ、ａは上記と同様である。） The silicone-modified tertiary amine represented by the formula (3) comprises a hydroxyl group of a hydroxyalkyl tertiary amine having at least one hydroxyl group and an isocyanate group of an organopolysiloxane having an isocyanate group represented by the following formula (4). It can be obtained by a urethane bond formation reaction.

(In formula (4), R ⁴ , R ⁵ , R ⁶ , R ⁷ , —OSiR ⁸ R ⁹ R ¹⁰ , n and a are the same as above.)

で表される。
（式中Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ｒ^６、Ｒ^７、ｍ、ｎ、ａは、上記と同様である。） The resulting silicone-modified tertiary amine has the following formula (5)

It is represented by
(Wherein R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , m, n, and a are the same as above).

Specific examples of the hydroxyalkyl tertiary amine having at least one hydroxyl group include dimethylaminoethanol, N-methyldiethanolamine, triethanolamine, diethylaminoethanol, N-ethyldiethanolamine, dipropylaminoethanol, N-propyldiethanolamine, dibutylaminoethanol. , N-butyldiethanolamine and the like. When ^two of R ¹ , R ² and R ^{3 in} the formula (1) form a ring, those derived from amines such as pyrrolidine and piperidine are used, and specific examples thereof include 1- ( 2-hydroxyethyl) pyrrolidine, 4-hydroxypiperidine, 1-piperidineethanol.

As the organopolysiloxane having an isocyanate group represented by the formula (4), TMSI is preferably used. (In the TMSI, in the formula (4), n is 3, a is 0, R ⁵ , R ^6. , R ⁷ is a methyl group). When a hydroxyalkyl tertiary amine having a hydroxyl group is reacted with TMSI, tristrimethylsiloxysilylpropylamine which is a silicone-modified tertiary amine can be obtained.

  Further, the silicone-modified tertiary amine of the formula (5) is prepared by dissolving 1 mol of a hydroxyalkyl tertiary amine having a hydroxyl group in an organic solvent such as toluene, and adding 1 to 1.2 mol of an isocyanate group-containing organopolysiloxane necessary for this. Prepared in a reaction vessel and reacted in an inert gas stream at 50 to 120 ° C. for about 5 to 10 hours. After completion of the reaction, the solvent was removed by an evaporator, followed by purification treatment such as decolorization and deodorization by conventional methods. It can also be obtained by doing.

  In the above reaction, a base catalyst or a metal catalyst can be used as necessary.

  EXAMPLES Hereinafter, the silicone-modified zwitterionic compound of the present invention and the production method thereof will be described more specifically with reference to examples, but the present invention is not limited to the following examples.

Example 1
TMSI (0.1 mol) is dropped into a toluene solution of dimethylaminoethanol (0.1 mol) at 60 to 80 ° C. and stirred at this temperature for 8 hours to complete the reaction, and then the solvent is removed by an evaporator. As a result, a colorless transparent liquid (silicone-modified tertiary amine) was obtained. Thereafter, the obtained liquid (silicone-modified tertiary amine) was dropped into a toluene solution of 1,3-propane sultone while stirring in a water bath, and a white solid was precipitated by stirring overnight at room temperature. This was filtered and washed with toluene and acetone to obtain a white solid represented by the following formula.

(Example 2)
TMSI (0.1 mol) is dropped into a toluene solution of dimethylaminoethanol (0.1 mol) at 60 to 80 ° C. and stirred at this temperature for 8 hours to complete the reaction, and then the solvent is removed by an evaporator. As a result, a colorless transparent liquid (silicone-modified tertiary amine) was obtained. Thereafter, the resulting liquid (silicone-modified tertiary amine) was dropped into a toluene solution of 1,4-butane sultone while stirring in a water bath, and a white solid was precipitated by stirring overnight at room temperature. This was filtered and washed with toluene and acetone to obtain a white solid represented by the following formula.

(Comparative Example 1)
To a toluene solution of 1,4-butane sultone (0.1 mol), dimethylaminoethanol was added dropwise with stirring in a water bath, and the mixture was stirred overnight to precipitate a white solid. This was filtered and washed with toluene and acetone to obtain a white solid represented by the following formula.

  Table 1 below shows the melting points of the compounds described in Example 1, Example 2, and Comparative Example 1.

  As shown in Table 1, the compounds of Examples 1 and 2 that are novel silicone-modified zwitterionic compounds containing siloxane of the present invention had a lower melting point than Comparative Example 1 that is a conventional zwitterionic compound. .

  Table 2 below shows the solubility of the compounds described in Example 1, Example 2, and Comparative Example 1 in various solvents.

The evaluation criteria are as follows.
○: dissolved or heated dissolved, Δ: partially dissolved, x: insoluble As shown in Table 2, the compounds of Examples 1 and 2 which are novel silicone-modified zwitterionic compounds containing siloxane of the present invention Compared with the comparative example 1 which is a zwitterionic compound, the solubility was high.

  As described above, the novel silicone-modified zwitterionic compound containing siloxane of the present invention has a melting point lower than that of the conventional zwitterionic compound and melts in a temperature range of 70 to 200 ° C. to form a liquid state. It has a property of high solubility in a solvent. For this reason, for example, it can be dissolved by heating as an antistatic agent and kneaded into a resin or the like, or dissolved in a solvent and mixed into the composition.

The present invention is not limited to the above embodiment. The above-described embodiment is an exemplification, and the present invention has any configuration that has substantially the same configuration as the technical idea described in the claims of the present invention and that exhibits the same effects. It is contained in the technical range.

Claims (5)

A silicone-modified zwitterionic compound represented by the following formula (1) having a quaternary ammonium ion cation moiety and a sulfonate ion anion moiety in the same molecule.

[Wherein R ¹ , R ² and R ³ may be the same or different and each represents an alkyl group having 1 to 6 carbon atoms, an aryl group, a fluorine-substituted alkyl group, a hydroxyl group-containing hydroxyalkyl group, and the following formula (2): One of the organopolysiloxane structures having a urethane bond represented is shown, and ^{two of} R ¹ , R ² and R ³ may form a ring, in which case an alkylene group is represented. At least one of R ¹ , R ² and R ³ has the structure of the following formula (2). l is an integer of 3 to 6.

(In the formula, R ⁴ is a monovalent organic group having 1 to 8 carbon atoms or a group having a siloxane bond, and R ⁵ , R ⁶ and R ⁷ are each a monovalent organic group having 1 to 8 carbon atoms and a siloxane bond. And a siloxy group represented by -OSiR ⁸ R ⁹ R ¹⁰ (R ⁸ , R ⁹ and R ¹⁰ are each a monovalent organic group having 1 to 8 carbon atoms), m is 1 4 is an integer, n is an integer from 1 to 10, and a is an integer from 0 to 2.)] 2. The silicone-modified zwitterionic compound according to claim 1, wherein in the formula (2), n is 3, R ⁵ , R ⁶ and R ⁷ are methyl groups, and a is 0. A silicone-modified zwitterionic compound represented by the following formula (1) is produced by reacting a silicone-modified tertiary amine represented by the following formula (3) with an alkyl sultone. A method for producing an ionic compound.

[Wherein R ¹ , R ² and R ³ may be the same or different and each has an alkyl group having 1 to 6 carbon atoms, an aryl group, a fluorine-substituted alkyl group, a hydroxyl group-containing hydroxyalkyl group, and the following formula (2): Any one of R ¹ , R ² , and R ³ may form a ring, and in this case, represents an alkylene group. At least one of R ¹ , R ² and R ³ has the structure of the following formula (2). l is an integer of 3 to 6.

(Wherein R ⁴ is a monovalent organic group having 1 to 8 carbon atoms or a group having a siloxane bond, and R ⁵ , R ⁶ and R ⁷ each have a monovalent organic group having 1 to 8 carbon atoms and a siloxane bond. And a siloxy group represented by —OSiR ⁸ R ⁹ R ¹⁰ (R ⁸ , R ⁹ and R ¹⁰ are each a monovalent organic group having 1 to 8 carbon atoms), m is 1 to 4; An integer, n is an integer from 1 to 10, and a is an integer from 0 to 2.]

(Wherein R ¹ , R ² and R ³ are the same as above) As the silicone-modified tertiary amine, a silicone-modified tertiary amine obtained by reacting a hydroxyl group of a hydroxyalkyl tertiary amine having at least one hydroxyl group with an organopolysiloxane having an isocyanate group represented by the following formula (4): The method for producing a silicone-modified zwitterionic compound according to claim 3, wherein:

[In the formula (4), R ⁴ , R ⁵ , R ⁶ , R ⁷ , —OSiR ⁸ R ⁹ R ¹⁰ , n and a are the same as above. ]   The method for producing a silicone-modified zwitterionic compound according to claim 4, wherein tristrimethylsiloxysilylpropyl isocyanate is used as the organopolysiloxane having an isocyanate group.