JP2010070697A - Self-emulsification type isocyanate compound and method for producing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a self-emulsification type isocyanate compound having a good external appearance, and to provide a method for producing the same. <P>SOLUTION: The self-emulsification type isocyanate compound is obtained by performing reaction of an imidazolium salt represented by general formula (1), an organic polyisocyanate compound, and an active hydrogen-containing compound, wherein, R<SP>1</SP>is 4-12C hydrocarbon, R<SP>2</SP>is 1-12C hydrocarbon, that may be substituted by hydroxyl group, or hydrogen atom, R<SP>3</SP>is 1-18C hydrocarbon that may be substituted by hydroxyl group. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to a self-emulsifying isocyanate compound and a method for producing the same.

Due to the recent demand for solvent removal, polyisocyanate compounds as raw materials for polyurethanes are required to have water dispersibility and self-emulsifying properties. As a method for preparing a polyisocyanate compound having self-emulsifying properties, a method in which methoxypolyethylene glycol is reacted with a polyisocyanate compound is known (Patent Document 1), and an ionic interface is added to a polyisocyanate compound to which methoxypolyethylene glycol is added. An activator is also added (Patent Document 2).
JP-A-5-222150 JP-A-9-71720

  However, the self-emulsifying isocyanate compound obtained by oxyalkylene compound capped at one end with an alkyl group, such as methoxypolyethylene glycol, disclosed in Patent Document 1 or 2, is a micelle of the compound when emulsified at high temperature. There is a problem that the particle size becomes extremely larger than the particle size when emulsified at a low temperature and the high-temperature emulsification stability is poor.

［式中、Ｒ^１は炭素数４〜１２の炭化水素基、Ｒ^２は水酸基で置換されていてもよい炭素数１〜１２の炭化水素基又は水素原子、Ｒ^３は水酸基で置換されていてもよい炭素数１〜１８の炭化水素基、をそれぞれ示し、Ｒ^４及びＲ^５は、それぞれ独立に、水素原子、炭素数１〜１８の炭化水素基、水酸基、アミノ基、ニトロ基、シアノ基又はカルボキシル基を示し、Ｘ⁻は、Ｃｌ⁻、Ｂｒ⁻、Ｉ⁻、ＢＦ_４ ⁻、ＮＯ_３ ⁻、ＣＨ_３ＳＯ_４ ⁻、Ｃ_２Ｈ_５ＳＯ_４ ⁻、Ｃ_３Ｈ_７ＳＯ_４ ⁻、Ｃ_４Ｈ_９ＳＯ_４ ⁻、ＣＨ_３Ｃ_６Ｈ_４ＳＯ_３ ⁻、又はＣＨ_３ＳＯ_３ ⁻を示す。但し、Ｒ^２及びＲ^３の少なくとも一方は水酸基を有していなければならない。］
Self-emulsifying type obtained by reacting an imidazolium salt represented by the following general formula (1) with an organic polyisocyanate compound as a self-emulsifying type isocyanate compound capable of forming stable micelles without depending on the temperature of emulsification There are isocyanate compounds.

[Wherein R ¹ is a hydrocarbon group having 4 to 12 carbon atoms, R ² is a hydrocarbon group or hydrogen atom having 1 to 12 carbon atoms which may be substituted with a hydroxyl group, and R ³ is substituted with a hydroxyl group. R ⁴ and R ⁵ each independently represent a hydrogen atom, a hydrocarbon group having 1 to 18 carbon atoms, a hydroxyl group, an amino group, a nitro group, or a cyano group. Or X ⁻ represents Cl ⁻ , Br ⁻ , I ⁻ , BF ₄ ⁻ , NO ₃ ⁻ , CH ₃ SO ₄ ⁻ , C ₂ H ₅ SO ₄ ⁻ , C ₃ H ₇ SO ₄ ⁻ , C _{^{4 H 9 SO 4 -, CH}} 3 C 6 H 4 SO 3 -, or _CH 3 SO ₃ ^- shows the. However, at least one of R ² and R ³ must have a hydroxyl group. ]

  The imidazolium salt is a stable micelle that does not depend on the temperature of emulsification by reacting with an organic isocyanate, especially an aromatic isocyanate such as 4,4'-diphenylmethane diisocyanate or 2,4-tolylene diisocyanate. It is possible to provide a self-emulsifying isocyanate compound capable of forming

  However, when the self-emulsifying isocyanate compound is produced, a product in which two molecules of imidazolium salt are reacted with one molecule of organic isocyanate is by-produced. Since the reaction by-product does not dissolve in the organic isocyanate and precipitates as a solid, not only the appearance is deteriorated but also the emulsifiability may be deteriorated because the modifier is reduced.

  As a method of suppressing the bimolecular reaction by-product, it can be reduced by a method such as lowering the reaction start temperature or increasing the stirring speed, but it is impossible to eliminate the reaction by-product completely. It was.

  Furthermore, the addition of acidic substances such as phosphate esters and acid anhydrides can prevent the formation of bimolecular reaction by-products, but the presence of acidic substances deteriorates the storage stability of the resulting self-emulsifying isocyanate compound, and Another problem is that it causes rust in storage cans.

Accordingly, an object of the present invention is to provide a self-emulsifying isocyanate compound which can form stable micelles without depending on the temperature of emulsification and has few impurities.

［式中、Ｒ^１は炭素数４〜１２の炭化水素基、Ｒ^２は水酸基で置換されていてもよい炭素数１〜１２の炭化水素基又は水素原子、Ｒ^３は水酸基で置換されていてもよい炭素数１〜１８の炭化水素基、をそれぞれ示し、Ｒ^４及びＲ^５は、それぞれ独立に、水素原子、炭素数１〜１８の炭化水素基、水酸基、アミノ基、ニトロ基、シアノ基又はカルボキシル基を示し、Ｘ⁻は、Ｃｌ⁻、Ｂｒ⁻、Ｉ⁻、ＢＦ_４ ⁻、ＮＯ_３ ⁻、ＣＨ_３ＳＯ_４ ⁻、Ｃ_２Ｈ_５ＳＯ_４ ⁻、Ｃ_３Ｈ_７ＳＯ_４ ⁻、Ｃ_４Ｈ_９ＳＯ_４ ⁻、ＣＨ_３Ｃ_６Ｈ_４ＳＯ_３ ⁻、又はＣＨ_３ＳＯ_３ ⁻を示す。但し、Ｒ^２及びＲ^３の少なくとも一方は水酸基を有していなければならない。］
The present invention is shown in the following (1) to (3).
(1) A self-emulsifying isocyanate compound obtained by reacting an imidazolium salt represented by the following general formula (1), an organic polyisocyanate compound and an active hydrogen-containing compound.

[Wherein R ¹ is a hydrocarbon group having 4 to 12 carbon atoms, R ² is a hydrocarbon group or hydrogen atom having 1 to 12 carbon atoms which may be substituted with a hydroxyl group, and R ³ is substituted with a hydroxyl group. R ⁴ and R ⁵ each independently represent a hydrogen atom, a hydrocarbon group having 1 to 18 carbon atoms, a hydroxyl group, an amino group, a nitro group, or a cyano group. Or X ⁻ represents Cl ⁻ , Br ⁻ , I ⁻ , BF ₄ ⁻ , NO ₃ ⁻ , CH ₃ SO ₄ ⁻ , C ₂ H ₅ SO ₄ ⁻ , C ₃ H ₇ SO ₄ ⁻ , C _{^{4 H 9 SO 4 -, CH}} 3 C 6 H 4 SO 3 -, or _CH 3 SO ₃ ^- shows the. However, at least one of R ² and R ³ must have a hydroxyl group. ]

(2) The self-emulsifying isocyanate compound according to (1), wherein the active hydrogen-containing compound has a hydroxyl group.

(3) The method for producing a self-emulsifying isocyanate compound according to (1) or (2).

  According to the present invention, a self-emulsifiable isocyanate compound capable of forming stable micelles without depending on the temperature of emulsification and free of bimolecular reaction by-products and free of uniform impurities is obtained. It becomes possible.

  Hereinafter, embodiments of the present invention will be described in detail.

［式中、Ｒ^１は炭素数４〜１２の炭化水素基、Ｒ^２は水酸基で置換されていてもよい炭素数１〜１２の炭化水素基又は水素原子、Ｒ^３は水酸基で置換されていてもよい炭素数１〜１８の炭化水素基、をそれぞれ示し、Ｒ^４及びＲ^５は、それぞれ独立に、水素原子、炭素数１〜１８の炭化水素基、水酸基、アミノ基、ニトロ基、シアノ基又はカルボキシル基を示し、Ｘ⁻は、Ｃｌ⁻、Ｂｒ⁻、Ｉ⁻、ＢＦ_４ ⁻、ＮＯ_３ ⁻、ＣＨ_３ＳＯ_４ ⁻、Ｃ_２Ｈ_５ＳＯ_４ ⁻、Ｃ_３Ｈ_７ＳＯ_４ ⁻、Ｃ_４Ｈ_９ＳＯ_４ ⁻、ＣＨ_３Ｃ_６Ｈ_４ＳＯ_３ ⁻、又はＣＨ_３ＳＯ_３ ⁻を示す。但し、Ｒ^２及びＲ^３の少なくとも一方は水酸基を有していなければならない。］ The imidazolium salt containing a hydroxyl group that can be used in the present invention is represented by the following general formula (1) such as 1-octyl-3- (2-hydroxyethyl) -imidazolium chloride.

[Wherein R ¹ is a hydrocarbon group having 4 to 12 carbon atoms, R ² is a hydrocarbon group or hydrogen atom having 1 to 12 carbon atoms which may be substituted with a hydroxyl group, and R ³ is substituted with a hydroxyl group. R ⁴ and R ⁵ each independently represent a hydrogen atom, a hydrocarbon group having 1 to 18 carbon atoms, a hydroxyl group, an amino group, a nitro group, or a cyano group. Or X ⁻ represents Cl ⁻ , Br ⁻ , I ⁻ , BF ₄ ⁻ , NO ₃ ⁻ , CH ₃ SO ₄ ⁻ , C ₂ H ₅ SO ₄ ⁻ , C ₃ H ₇ SO ₄ ⁻ , C _{^{4 H 9 SO 4 -, CH}} 3 C 6 H 4 SO 3 -, or _CH 3 SO ₃ ^- shows the. However, at least one of R ² and R ³ must have a hydroxyl group. ]

Examples of the hydroxyl group-containing compound that can be used in the present invention include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, tert-butanol, 1-pentanol, 1-hexanol, 1-hexanol, Monoalcohols such as octanol and 2-ethylhexanol, ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1 6-hexanediol, 3-methyl-1,5-pentanediol, neopentyl glycol, 1,8-octanediol, 1,9-nonanediol, diethylene glycol, 1,4-cyclohexanedimethanol, or ethylene of bisphenol A oxide Is a hydroxyl group-containing compound such as glycol such as propylene oxide adduct, triol such as glycerin and trimethylolpropane, ammonia, monomethylamine, dimethylamine, monoethylamine, diethylamine, monopropylamine, dipropylamine, monobutylamine, dibutylamine, Examples include amino compounds such as ethylenediamine, diethylenetriamine, triethylenetetramine, xylenediamine, isophoronediamine, and monoethanolamine, amino alcohols, hexamethylenediamine, xylenediamine, and isophoronediamine. Said compound can be used individually or in mixture of 2 or more types.

  When an imidazolium salt and an active hydrogen group-containing compound are added to the organic polyisocyanate compound, the imidazolium salt and the active hydrogen group-containing compound must be added simultaneously in a uniform solution. If it is not a uniform liquid, a portion having a high imidazolium salt concentration is generated locally, which causes generation of a bimolecular reactant.

  The active hydrogen group-containing compound needs to be reacted at the same time as reacting the organic polyisocyanate compound and the imidazolium salt as described above, but before reacting with the organic polyisocyanate compound and the imidazolium salt, the organic polyisocyanate compound and the imidazolium salt are reacted. You may make it react with an isocyanate compound, and after making an imidazolium salt and an organic polyisocyanate compound react, it is also possible to make it react with the said prepolymer further.

  The active hydrogen group is preferably a hydroxyl group because of its relatively mild reactivity with isocyanate and good solubility after reaction with isocyanate groups. Moreover, a monool compound is preferable in order to suppress an increase in viscosity due to the reaction.

  Examples of the organic polyisocyanate compound that can be used in the present invention include 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, xylene-1,4-diisocyanate, xylene-1,3-diisocyanate, 4, 4'-diphenylmethane diisocyanate, 2,4'-diphenylmethane diisocyanate, 2,2'-diphenylmethane diisocyanate, 4,4'-diphenyl ether diisocyanate, polymethylene polyphenylene polyisocyanate (polymeric MDI), 2-nitrodiphenyl-4 4'-diisocyanate, 2,2'-diphenylpropane-4, 4'-diisocyanate, 3,3'-dimethyldiphenylmethane-4, 4'-diisocyanate, 4,4'-diphenylpropane diisocyanate , Aromatic diisocyanates such as m-phenylene diisocyanate, p-phenylene diisocyanate, naphthylene-1,4-diisocyanate, naphthylene-1,5-diisocyanate, 3,3'-dimethoxydiphenyl-4,4'-diisocyanate, tetramethylene Aliphatic diisocyanates such as diisocyanate, hexamethylene diisocyanate, 3-methyl-1,5-pentane diisocyanate, lysine diisocyanate, isophorone diisocyanate, hydrogenated tolylene diisocyanate, hydrogenated xylene diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated tetramethylxylene diisocyanate Alicyclic diisocyanates such as polymers, polymers thereof, and mixtures of two or more thereof. And the like.

  The organic polyisocyanate compound may be modified with a polymer polyol. The polymer polyol is a compound having one or more hydroxyl groups, and examples thereof include long-chain polyols, specifically, polyester polyols, polycarbonate polyols, polyether polyols, acrylic polyols, and copolyols thereof. These long chain polyols may be used alone or in combination of two or more. Modification with these long-chain polyols may be performed simultaneously with modification with an imidazolium salt or may be performed separately. The number average molecular weight of these long-chain polyols is preferably 300 to 10,000.

  Polyester polyols include dicarboxylic acids such as succinic acid, adipic acid, sebacic acid, azelaic acid, terephthalic acid, isophthalic acid, orthophthalic acid, hexahydroterephthalic acid, hexahydroisophthalic acid, hexahydroorthophthalic acid, naphthalenedicarboxylic acid, One or more of an acid ester or an acid anhydride, and ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,3-butanediol, 1,4-butanediol, 1,5-pentane Diol, 1,6-hexanediol, 3-methyl-1,5-pentanediol, neopentyl glycol, 1,8-octanediol, 1,9-nonanediol, diethylene glycol, 1,4-cyclohexanedimethanol, or bisphenol A's Ethile A polyester polyol or a polyesteramide polyol obtained by a dehydration condensation reaction with one or more of glycols such as oxides or propylene oxide adducts, hexamethylene diamine, xylene diamine, isophorone diamine, diamine such as monoethanolamine, or amino alcohol. Can be mentioned. Moreover, the lactone type | system | group polyester polyol obtained by ring-opening polymerization of cyclic ester (lactone) monomers, such as (epsilon) -caprolactone, is mentioned.

  Examples of the polycarbonate polyol include those obtained by a dealcoholization reaction between a polyhydric alcohol and diethylene carbonate, dimethyl carbonate, diethyl carbonate, diphenyl carbonate, or the like. Examples of the polyhydric alcohol include ethylene glycol, 1,3-propylene glycol, 1,2-propylene glycol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, and 1,6-hexa. Examples include methylenediol, 3-methyl-1,5-pentanediol, neopentyl glycol, 1,8-octanediol, 1,9-nonanediol, diethylene glycol, 1,4-cyclohexanedimethanol and the like.

As the polyether polyol, polyethylene glycol having a number average molecular weight of 300 to 10,000 having 1 to 5 functional groups obtained by ring-opening polymerization of ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran or the like using an initiator described later, Polypropylene glycol, polytetramethylene ether glycol, and the like, and polyether polyols obtained by copolymerization thereof, and polyester ether polyols using the above-described polyester polyols and polycarbonate polyols as initiators are also included. As an initiator for obtaining the polyether polyol, various monoalcohols having 1 to 5 functional groups and a number average molecular weight of 18 to 500, glycol, glycol ether, monoamine, diamine, aminoalcohol, water, urea and the like are used. Can do. Said compound can be used individually or in mixture of 2 or more types.

The polymer polyol is prepared by reacting the imidazolium salt with the organic polyisocyanate compound before reacting with the organic polyisocyanate compound and the imidazolium salt, simultaneously with the reaction with the imidazolium salt and the organic polyisocyanate compound. After the polymer is formed, it can be reacted with an organic polyisocyanate compound or the prepolymer.

  The self-emulsifying isocyanate compound of the present invention may be reacted by adding a homogeneous solution in which the imidazolium salt of the general formula (1) and the active hydrogen group-containing compound are dissolved at once to the organic polyisocyanate compound, It is also possible to react by gradually dropping. The reaction temperature is preferably 0 ° C to 120 ° C, more preferably 10 ° C to 100 ° C. If the reaction temperature is less than 0 ° C., the reaction may not proceed sufficiently. Conversely, if the reaction temperature exceeds 120 ° C., undesirable reactions such as isocyanurate formation and allophanate formation may occur. Although there is no limitation in particular as reaction time, after mixing all the raw materials, time until it reaches a target isocyanate content is required, and it is preferable that it is 0.5 to 20 hours.

  The equivalent ratio of the imidazolium salt to the active hydrogen group-containing compound (active hydrogen group / imidazolium salt) is preferably in the range of 5.4 to 100, and particularly preferably in the range of 5.7 to 10. When this equivalent ratio is less than 5.4, a bimolecular reactant may occur. When the equivalent ratio is more than 100, when trying to introduce an imidazolium salt for obtaining the required emulsifiability, the viscosity of the self-emulsifying isocyanate compound increases excessively, resulting in problems in workability and the like. There is a case.

In obtaining a self-emulsifying isocyanate compound, an equivalent ratio (isocyanate group) of an isocyanate group and an active hydrogen group (the above-mentioned hydroxyl group-containing compound, polymer polyol, and active hydrogen group relating to all active hydrogen group-containing compounds having other than hydroxyl groups). / Active hydrogen group) is preferably in the range of 5 to 1000, particularly preferably in the range of 10 to 500. When this equivalent ratio is less than 5, the viscosity of the self-emulsifying isocyanate compound increases excessively, which may cause problems in workability and the like. Moreover, when this equivalent ratio exceeds 1000, self-emulsification may fall.

  EXAMPLES Hereinafter, although this invention is demonstrated more concretely based on an Example and a comparative example, this invention is not limited to a following example at all.

(Synthesis Example 1)
A reactor equipped with a stirrer, a cooling tube, a nitrogen introduction tube and a thermometer was purged with nitrogen, and then 100.0 g of 1- (2-hydroxyethyl) -imidazole and 198.9 g of 1-chlorooctane were charged into the reactor. The mixture was reacted for 46 hours while stirring at 100 ° C. Thereafter, it was confirmed by ¹ H-NMR that there was no unreacted 1- (2-hydroxyethyl) -imidazole. Unreacted 1-chlorooctane was distilled off from this reaction mixture at 140 ° C. and 10 mmHg to obtain an imidazolim salt (onium salt) “A”. After further cooling to 50 ° C., 186 g of methanol was added and stirred to obtain a uniform imidazolium salt / active hydrogen compound solution “B-1”.

Example 1
A reactor equipped with a stirrer, a cooling tube, a nitrogen introducing tube, and a thermometer was purged with nitrogen, and 982 g of polymeric MDI (manufactured by Nippon Polyurethane Industry Co., Ltd., trade name “MR-200”) was charged into the reactor. Next, 18 g of the imidazolim salt composition “B-1” was charged while stirring at room temperature, and reacted for 1.5 hours while stirring at 50 ° C. to obtain an isocyanate (NCO) content of 28.9% and a viscosity at 25 ° C. A self-emulsifying polyisocyanate compound “P1” of 370 mPa · s was obtained.

(Examples 2 to 16)
The same operation was performed in the same apparatus as in Example 1 in the amounts shown in Tables 1 and 2 to obtain imidazolium salt / active hydrogen compound solution “P2 to 16”.

(Comparative Example 1)
A reactor equipped with a stirrer, a cooling tube, a nitrogen introducing tube, and a thermometer was purged with nitrogen, and then 990 g of polymeric MDI (manufactured by Nippon Polyurethane Industry Co., Ltd., trade name “MR-200”) was charged into the reactor. Next, 10 g of the imidazolim salt composition “A” was charged while stirring at room temperature, and reacted for 1 hour while stirring at 50 ° C., with an isocyanate (NCO) content of 30.4% and a viscosity at 25 ° C. of 240 mPa · s. A self-emulsifying polyisocyanate compound “P17” was obtained.

(Comparative Example 2)
A reactor equipped with a stirrer, a cooling tube, a nitrogen introduction tube, and a thermometer was purged with nitrogen, and then 970 g of polymeric MDI (manufactured by Nippon Polyurethane Industry Co., Ltd., trade name “MR-200”) was charged into the reactor. Next, 10 g of the imidazolim salt composition “A”, which was uniformly dissolved in 20 g of acetone in advance, was added while stirring at room temperature, and reacted for 1.5 hours while stirring at room temperature of 50 ° C. to obtain an isocyanate (NCO) content of 29. A self-emulsifying polyisocyanate compound “P18” having a viscosity of 230 mPa · s at 25% at 8% was obtained.

(Comparative Example 3)
A reactor equipped with a stirrer, a cooling pipe, a nitrogen introduction pipe and a thermometer was purged with nitrogen, and then 990 g of polymeric MDI (manufactured by Nippon Polyurethane Industry Co., Ltd., trade name “MR-200”) and 2-ethylhexyl acid were added to the reactor. 5 g of phosphate (JP-508 manufactured by Johoku Chemical Industry Co., Ltd.) was charged. Next, 10 g of the imidazolim salt composition “A” was charged while stirring at room temperature, and reacted for 1 hour while stirring at 50 ° C., so that the isocyanate (NCO) content was 30.4% and the viscosity at 25 ° C. was 240 mPa · s. A self-emulsifying polyisocyanate compound “P19” was obtained.

(Comparative Example 4)
A reactor equipped with a stirrer, a cooling tube, a nitrogen introducing tube, and a thermometer was purged with nitrogen, and 982 g of polymeric MDI (manufactured by Nippon Polyurethane Industry Co., Ltd., trade name “MR-200”) was charged into the reactor. Next, 8 g of methanol was charged while stirring at room temperature, and 10 g of imidazolim salt composition “A” was charged while stirring at room temperature. The mixture was reacted at room temperature at 50 ° C. for 1.5 hours to react with isocyanate (NCO) content. A self-emulsifying type polyisocyanate compound “P20” having a viscosity of 370 mPa · s at 28.9% at 25 ° C. was obtained.

  About the self-emulsification type polyisocyanate compound of P1-P20, the measurement result of an external appearance is shown to Tables 1-3 with the data of a modification amount, NCO content, and a viscosity.

In Comparative Examples 1 and 2, the appearance was poor or the storage stability was poor, but in Example 1, it was found that both the appearance and the storage stability were maintained.

(Appearance evaluation method)
Appearance: The appearance was visually observed.

◎: No fine suspended matters are observed at all ○: Fine suspended matters are slightly observed △: Fine suspended matters are small ×: Many fine suspended matters are observed

(Evaluation method of storage stability)
Storage stability: Viscosity after 2 months at 50 ° C. is 2 times or less immediately after synthesis.
Viscosity measurement method: Viscosity at 25 ° C. was measured using a B-type rotational viscometer DVL-BII (manufactured by Tokimec Co., Ltd.).

The self-emulsifying type isocyanate compound of the present invention is a binder for a molded body of a lignocellulosic material such as medium density fiberboard, particle board, or oriented strand board, magnetic tape binder, paint, adhesive, thermoplastic resin, thermosetting. It can be used for the production of resins, flexible foams and rigid foams.

Claims (3)

A self-emulsifying isocyanate compound obtained by reacting an imidazolium salt represented by the following general formula (1), an organic polyisocyanate compound and an active hydrogen group-containing compound.

[Wherein R ¹ is a hydrocarbon group having 4 to 12 carbon atoms, R ² is a hydrocarbon group or hydrogen atom having 1 to 12 carbon atoms which may be substituted with a hydroxyl group, and R ³ is substituted with a hydroxyl group. R ⁴ and R ⁵ each independently represent a hydrogen atom, a hydrocarbon group having 1 to 18 carbon atoms, a hydroxyl group, an amino group, a nitro group, or a cyano group. Or X ⁻ represents Cl ⁻ , Br ⁻ , I ⁻ , BF ₄ ⁻ , NO ₃ ⁻ , CH ₃ SO ₄ ⁻ , C ₂ H ₅ SO ₄ ⁻ , C ₃ H ₇ SO ₄ ⁻ , C _{^{4 H 9 SO 4 -, CH}} 3 C 6 H 4 SO 3 -, or _CH 3 SO ₃ ^- shows the. However, at least one of R ² and R ³ must have a hydroxyl group. ]
The self-emulsifying isocyanate compound according to claim 1, wherein the active hydrogen group-containing compound has a hydroxyl group.
The method for producing a self-emulsifying isocyanate compound according to claim 1 or 2, wherein a composition obtained by mixing an organic polyisocyanate compound, an imidazolium salt and a hydroxyl group-containing compound is reacted.