JPS6346203A - Water-dispersible resin - Google Patents

Abstract

PURPOSE:To provide the titled resin useful as adhesives, coatings, etc., consisting of a blocked isocyanate carbonyl group and acidic or basic group-contg. polymer. CONSTITUTION:(A) A blocked acyl isocyanate compound of formula I (R is H or lower alkyl; B is residue formed by eliminating, from blocking agent, the H involved in the addition reaction with the isocyanate group), (B) an acidic or basic group-contg. ethylene unsaturated compound and, if needed, (C) another polymerizable monomer are polymerized followed by neutralization of the acidic or basic group in the resultant polymer, thus obtaining the objective resin consisting of a blocked isocyanate carbonyl group(of formula II)-contg. polymer with a molecular weight 1,000-100,000 to which (1) 1-99wt% of blocked isocyanate carbonyl group and (2) 1-90wt% of acidic or basic group (e.g. carboxylic acid group, phosphoric acid group, amino group, etc.) are connected with 0.1-100wt% of said acidic or basic group neutralized.

Description

DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a water-dispersible resin, particularly a water-dispersible resin comprising a blocked isocyanatocarbonyl group-containing polymer.

(Prior Art) Compounds having isocyanato groups are widely used in various fields including polymer chemistry due to their excellent reactivity. In particular, compounds that have both a polymerizable carbon-carbon unsaturated group and an isocyanate group in the same molecule are used in a wide range of industrial technology fields because both of these functional groups participate in various reactions with different reaction mechanisms. Be able to do it. Focusing on such usefulness, the present inventors previously provided an acylisocyanate compound represented by the following formula [e.g., JP-A-60-115557]: CH, -
(It)C-N=C=0 [wherein R represents a hydrogen atom or a lower alkyl group (eg, methyl, ethyl, propyl, butyl). ].

This compound has an isocyanatocarbonyl group j (-C-N=C=O), and the carbonyl group adjacent to the isocyanato group increases the activity of the isocyanato group and is in a state where it can carry out a wide variety of addition reactions. be.

(Object of the Invention) The present invention aims to provide a polymer useful as a resin component in a fat composition such as a paint or an adhesive by utilizing the above-mentioned acylisocyanate compound (El).

(Contents of the invention) The gist of the present invention is that the main chain consisting of carbon-carbon bonds has the following formula: % formula % [wherein B is a residue obtained by excluding the hydrogen atom involved in the addition reaction with the isonoanato group from the blocking agent] shows. ] The blocked isocyanatocarbonyl group represented by 1
A blocked isocyanatocarbonyl group-containing polymer (but ,
0.1-100% of the acidic or basic groups are neutralized. ) consists of a water-dispersible resin.

The polymer constituting the above water-dispersible resin has the formula: % formula % (
1) ]:1 [wherein R and B have the same meanings as above. ] A blocked acylisocyanate compound represented by the above formula, an ethylenically unsaturated compound containing an acidic group or a basic group, and other polymerizable monomers as necessary are polymerized, and the acidic group or basic group in the resulting polymer is neutralized. Obtained by summing.

The blocked acylisocyanate compound (1) can be obtained by blocking the acyl isocyanate compound (II) with a blocking agent represented by the formula:% formula %(). Acyl isocyanate compound ([[) is
It may be obtained by the method described in JP-A No. 60-115557, and may be obtained by the method described in JP-A-60-115557.
ie～(akromoleklare Chemie)
+31 (1970) 247-257 (No, 319
It may be produced via the intermediate described in 9). Usually α−
It can be produced by the reaction of alkylacrylamide and oxalyl halide. The reaction is carried out in the presence of an inert solvent such as a halogenated hydrocarbon at a temperature of 0 to 80°C.

As mentioned above, acyl isocyanate compound (II)
has the potential for various reactions,
When the blocking agent (III) is reacted with this, in addition to and/or instead of the addition reaction between the desired acyl isocyanate compound (II) and the blocking agent (III), the acyl isocyanate compound (It) itself is quantification,
Trimerization, multimerization (polymerization), polymerization of the produced blocked acylisocyanate compound (1), amide 9N of the produced blocked acylisocyanate compound (1), etc.
It was predicted that various side reactions would proceed, such as the reaction between the H group and the acylisonoanate compound (II), but in reality, the above desired reaction proceeds preferentially in a temperature range that does not exceed at least 100°C. This was confirmed.

Especially at relatively low temperatures that do not exceed room temperature (0-30℃),
Only desired reactions proceed quantitatively, and various predicted side reactions can be virtually completely avoided.

As the blocking agent (I[[), a compound having active hydrogen is used, and monofunctional alcohols and phenols are usually used. Specifically, methanol, ethanol, chloroethanol, propatool, butanol,
Pentanol, hexanol, heptatool, octatool, nonanol, 3.3.5-)limethylhexanol, 2-ethylhexanol, phenylcarbinol,
Methylphenyl carbinol, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, phenol, cresol, xylenol, nitrophenol, chlorophenol, ethylphenol, t-
Examples include butylphenol, nonylphenol, -functional polyethylene or polypropylene oxide (eg Carbowax 550). In addition to these, active methylene compounds (e.g. acetylacetone, diethyl malonate), lactams (e.g. propyrolactam, butyrolactam, valerolactam, caprolactam), N-1 droxyimide (e.g. N-hydroxyphthalimide,
N-hydroxyglutarimide, N-hydroxysuccinimide), oximes (e.g. methyl ethyl ketoxime, acetone oxime, cyclohexanone oxime)
, imidazoles (for example, 1,3-imidazole), triazoles (for example, 1.2,3-benzotriazole), amines (for example, dicyclohexylamine), etc. may be used.

The blocking agent (I[[) is often liquid at room temperature, and may itself serve as a medium for the blocking reaction.
An inert solvent may be used regardless of whether the blocking agent (II[) is liquid or solid. There are no particular restrictions on the inert solvent as long as it does not adversely affect the reaction, and various solvents can be used, including aliphatic hydrocarbons such as pentane, hexane, and heptane, and aromatic solvents such as benzene, toluene, and xylene. Hydrocarbons, alicyclic hydrocarbons such as cyclohexane, methylchlorohexane, and decalin, petroleum hydrocarbons such as petroleum ether and petroleum benzene, and halogenated hydrocarbons such as carbon tetrachloride, chloroform, and 1°2-dichloroethane. ethyl ether,
From ethers such as isopropyl ether, anisole, dioxane, and tetrahydrofuran, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, acetophenone, and isophorone, esters such as ethyl acetate, butyl acetate, acetonitrile, dimethylformamide, dimethyl sulfoxide, etc. It may be selected as appropriate. These may be used alone or as a mixture.

It is generally preferable to carry out the blocking reaction at a temperature of -20 to 100°C, but it is advantageous to carry out the blocking reaction at around room temperature (0 to 30°C). At high temperatures of 100° C. or higher, side reactions may occur, while at too low temperatures the reaction rate decreases, which is disadvantageous. Although the use of a tin-based catalyst may be considered during the reaction, the necessity of using a catalyst is usually not recognized.

According to the present invention, since the active sites of the blocked acylisocyanate compound (I) are blocked, a radical addition polymerization reaction based on the ethylenically unsaturated group is not possible with an ethylenically unsaturated compound containing an acidic group or a basic group. This makes it possible to introduce acidic or basic groups into the polymer chain that impart water dispersibility. The acidic or basic group introduced into the polymer chain is preferably a carboxylic acid group, a sulfonic acid group, a phosphoric acid group, or an amino group. Examples of ethylenically unsaturated compounds having at least these groups include unsaturated acids (such as acrylic acid, methacrylic acid, crotonic acid, cinnamic acid, 2-isopropylacrylic acid, trans-2
-decenoic acid, cis-2-decenoic acid, α-chloroacrylic acid, β-trans-nitroacrylic acid), unsaturated sulfonic acids such as 2-sulfoethyl acrylate, 2-sulfoethyl methacrylate, ternary-butylacrylamide Sulfonic acid, 4-sulfophenyl acrylate,
p-vinylbenzenesulfonic acid), unsaturated phosphoric acids such as acid phosphooxyethyl methacrylate, 3-
Chloro-2-amide phosphooxypropyl methacrylate, acid phosphooxypropyl methacrylate, vinyl phosphate, isopropenyl phosphate), unsaturated amines (e.g. allylamine, 0-aminostyrene, m-aminostyrene, t-butylamino methacrylate) ethyl, 7
-amino-3,7-trimethyloctyl acrylate, 2
-dimethylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate, 2-diethylaminoethyl acrylate, 2-diethylaminoethyl methacrylate, 3-diethylaminopropyl acrylate, N-(
3-isopropylaminopropyl) methacrylamide,
vinylpyridine), etc. These may be used alone or as a mixture.

Other polymerizable monomers used as needed may be monomers that do not have active hydrogen or monomers that have active hydrogen.

Examples of monomers without active hydrogen include monoolefins and diolefins such as styrene, α-methylstyrene, α-ethylstyrene, isobutylene (2-
Methyl-propane-1), 2-methyl-butene-1,2
-Methyl-pentene-1,2,3-dimethyl-butene-
1,2,3-dimethylbentene-1,2,4-dimethyl-pentene-1,2,3,3-trimethyl-hebutene-1,2,3-dimethyl-hexene-1,2,4- Dimethyl-hexene-1,2,5-dimethyl-hexene-1
12-methyl-3-ethyl-pentene-1,2,3,3
-) trimethyl-pentene-112゜3.4-trimethyl-pentene-1,2,3,4-trimethyl-pentene-
1,2-Methyl-octene-112,6-tmethyl-hebutene-1,2゜6-tmethyl-octene-1,2.3
-dimethyl-decene-1,2-methyl-nonadecene-1
1 ethylene, propylene, butylene, amylene, hexylene, butanoene-1,3, isoprene), 10-genated monoolefins and diolefins (e.g. α-chlorostyrene, α-bromostyrene, 2,5-dichlorostyrene, 2 .5-dipromostyrene, 3,4-dichlorostyrene, ortho, meta and para-fluorostyrene, 2,6-dichlorostyrene, 2,6-difluorostyrene, 3-fluoro-4-chlorostyrene, 3-chloro- 4-fluorostyrene, 2,4.5-trichlorostyrene, dichloromonofluorostyrene, 2-chloropropene, 2-chlorobutene, 2-chloropentene, 2-
Chlorohexene, 2-chloroheptene, 2-bromobutene, 2-bromoheptene, 2-fluorohexene, 2-
Fluorobutene, 2-iodopropene, 2-iodopentene, 4-bromoheptene, 11-chloroheptene, 4
-Fluoroheptene, nos and trans-1,2-dichloroethylene, 1,2-dibromoethylene, 1,2-
Difluoroethylene, l, 2-short ethylene, chloroethylene (vinyl chloride), 1.1-dichloroethylene (vinylidene chloride), bromoethylene, fluoroethylene, iodoethylene, 1.1-dibromoethylene, 1.1-difluoroethylene, 1,1-short ethylene, 1,1゜2-trifluoroethylene, chlorobutadiene), esters of organic and inorganic acids (e.g. vinyl acetate, vinyl propionate, vinyl butyrate, vinyl isobutyrate, vinyl valerate, vinyl caproate, vinyl acetate, vinyl benzoate, vinyl toluate, vinyl p-chlorobenzoate, vinyl 〇-chlorobenzoate), vinyl p-methoxybenzoate, vinyl p-ethoxybenzoate, methyl methacrylate, Ethyl methacrylate, propyl methacrylate, butyl methacrylate, amyl methacrylate, hexyl methacrylate, heptyl methacrylate, octyl methacrylate, decyl methacrylate, methyl crotonate, ethyl tiglate, methyl acrylate, ethyl acrylate, propyl acrylate, isopropyl acrylate, butyl acrylate, isobutyl acrylate, Amyl acrylate, hexyl acrylate, 2-ethylhexyl acrylate, heptyl acrylate, octyl acrylate, 3.5.5-) dimethylhexyl acrylate, decyl acrylate and dodecyl acrylate, isopropenyl acetate, isopropenyl propionate, isopropenyl butyl acrylate isopropenyl isobutyrate, isopropenyl valerate, isopropenyl caproate, isopropenyl acetate, isopropenyl benzoate, isopropenyl-p-chlorobenzoate, isopropenyl-0-chlorobenzoate, isopropenyl-0-bromobenzoate , isopropenyl-m-chlorobenzoate, isopropenyl toluate, isopropenyl-α-chloroacetate, isopropenyl-α-bromopropionate, vinyl-α-chloroacetate, vinyl-α-bromoacetate, vinyl-α- Chloropropionate, vinyl-α-bromopropionate, vinyl-α-iodopropionate, vinyl-α-chlorobutyrate, vinyl-α-chlorovalerate, vinyl-α-bromovalerate, allyl chloride, Allyl cyanide, allyl bromide, allyl fluoride, allyl iosite, allyl chloride carbonate, allyl nitrate, allyl thiocyanate, allyl formate, allyl acetate, acetate propionate, allyl butyrate, allyl valerate, allyl caproate, allyl -3,5,5-trimethylhexaate, allyl benzoate, allyl acrylate, allyl crotonate, allyl oleate, allyl chloroacetate, allyl trichloroacetate, allyl chloropropionate, allyl chlorovalerate, allyl lactate, allyl pyruvate , allylaminoacetate,
Allyl acetoacetate, allyl thioacetate, methallyl chloride, methallyl cyanide, methallyl acetate, methallyl chloroacetate, β-ethyl allyl acetate, β-propyl allyl acetate, 1-buten-4-ol acetate, 2-methyl- Butene-・1-
All acetate, 2-(2,2-dimethylpropyl)
-1-buten-4-ol acetate, 1-pentene-
4-ol acetate, methyl-α-chloroacrylate, methyl-α-bromoacrylate, methyl-α-fluoroacrylate, methyl-α-iodoacrylate, ethyl-α-chloroacrylate, propyl-α-chloroacrylate, isopropyl-α -bromoacrylate, amyl-α-chloroacrylate, decyl-α-
Chloroacrylate, Methyl-α-cyanoacrylate, Ethyl-α-cyanoacrylate, Amyl-α-cyanoacrylate, Decyl-α-Noanoacrylate, Diallyl Malenate, Noethyl Maleate, Diallyl Malenate, Dimethyl Fumarate, Diethyl fumarate, diallylmalenit, noethylglutaconate), organic nitriles (eg, acrylonitrile, methacrylaterile, ethacrylonitrile, 3-octenenitrile, crotonitrile, oleonitrile), and the like.

Examples of monomers having active hydrogen include unsaturated alcohols (for example, monoesters of the above-mentioned unsaturated acids and glycols (ethylene glycol, propylene glycol, etc.), croton alcohol, cinnamyl alcohol,
(0-hydroxystyrene), unsaturated amides (for example, acrylic acid amide, methicrylic acid amide, crotonic acid amide, cinnamic acid amide, p-benzamide styrene), and the like.

Other polymerizable monomers of this type may also be used, either alone or in mixtures.

Polymerization is carried out by radical copolymerization of a mixture of the above polymerizable monomers in a solvent inert to polymerization. As the polymerization initiator, common radical initiators are preferably used, and specific examples thereof include azobisisobutyronitrile, benzoyl peroxide, cumene hydroperoxide, tetramethylthiuram disulfide, 2,2-azobis(4-methoxy -2°-4-dimethylvaleronitrile), acetylcyclohexylsulfonyl peroxide, 2.2°-azobis(2,4-dimethylvaleronitrile), and the like. The amount of initiator used is usually about 0.1 to 10% by weight based on the total amount of polymerizable monomers. Polymerization temperature is usually about 20
-200'C, preferably about 80-150C. The inert solvent for polymerization may be a blocking agent used in the blocking reaction, an inert solvent, or a mixture thereof. Using a blocking agent as a polymerization solvent prevents a side reaction between the blocked isocyanatocarbonyl group in the blocked acylisocyanate compound (I) and the active hydrogen in the ethylenically unsaturated compound containing an acidic group or a basic group. It is advantageous in that it suppresses and prevents gelation. Alcohols are particularly preferred as the blocking agent used as the polymerization solvent.

The polymerization reaction may be carried out by adding a polymerization initiator to the mixture of the polymerizable monomer and solvent. In addition, when a blocking agent is used as a polymerization solvent, the acyl isocyanate compound (II) is mixed into a large amount of the blocking agent to advance the blocking reaction, and then the other polymerizable monomer and the polymerization initiator are mixed. The polymerization reaction may be carried out by mixing . The blending ratio of the polymerizable monomers is based on the total amount of the blocked acylisocyanate compound (approximately 1 to 9
9% by weight, about 1 to 90% by weight of ethylenically unsaturated compounds containing acidic or basic groups, and the remainder may be other polymerizable monomers used as required.

During polymerization, other additives such as polymerization regulators may be added as desired.

The resulting polymer has its acidic or basic groups neutralized to impart water dispersibility. When acid groups are introduced into the blocked isocyanatocarbonyl group-containing polymer, neutralization is carried out with a base, and when basic groups are introduced, neutralization is carried out with an acid. Examples of acids used for neutralization include organic acids such as lactic acid, acetic acid, and propionic acid, and inorganic acids such as sulfuric acid and hydrochloric acid. It may also be a polymeric acid such as polycarboxylic acid. The base is preferably an organic base such as methylamine, ethylamine, methylethylamine, triethylamine, diethylethanolamine, pyridine, or an inorganic base such as sodium hydroxide or potassium hydroxide. It may also be a base of a polymer m such as a polyamine. The amount of neutralization is about 0.1-100% of the acid or base in the polymer. If it is less than about 0.1%, sufficient water dispersibility cannot be obtained.

Dispersion may be carried out by any appropriate method. After neutralizing the polymer, water may be added thereto, or after neutralization, the organic solvent may be removed and the polymer may be soaked in water to form a dispersion. Alternatively, after polymer synthesis, only the solid content may be taken out, dispersed in water or subjected to QfD, and then neutralized.

Note that the neutralized polymer, which is the main body of the water-dispersible resin of the present invention, can be prepared by methods other than those described above. For example, when blocking the acylisocyanate compound (II), in addition to an active hydrogen atom as a blocking agent, N,
If you use N-dimethylaminoethanol, you can simultaneously block isocyanate groups and block acidic or basic groups (N
, in the case of N-trimethylaminoethanol, a basic group (N,N-dimethylaminoethyl group) is introduced. Therefore, when performing polymerization using the blocked acylisocyanate compound (1), it is not necessary to coexist with an ethylenically unsaturated compound having an acidic group or a basic group. It is possible to obtain polymers with functional groups,
In this case, it is possible to impart good water dispersibility to the polymer by neutralizing the acidic or basic groups as described above. Note that the above-mentioned restrictions regarding the content of the blocked isocyanatocarbonyl group and acidic group or basic group and the degree of neutralization of the acidic group or basic group are also applied in this case.

(Functions and Effects) The prosolated isocyanatocarbonyl group in the polymer thus produced is easily dissociated by heat, light, a catalyst, etc. to generate a reactive isocyanatocarbonyl group. In particular, blocked isocyanatocarbonyl groups can be dissociated at lower temperatures than blocked isocyanato groups. The isocyanatocarbonyl group generated by dissociation is used as a reaction site for crosslinking reaction. The bonds generated by crosslinking are usually acylurethane bonds or acylurea bonds, which have strong intermolecular cohesive force and a high ability to form intermolecular hydrogen bonds.

According to the present invention, the acidic group or basic group introduced into the polymer chain is neutralized, and water dispersibility is imparted to the polymer having a blocked isonoanatocarbonyl group. The dispersed resin is cured in the presence of a crosslinking agent if necessary, and the resulting cured product has high adhesion, high adhesion, high image clarity, and high heat resistance. Therefore, the composition obtained by dispersing the water-dispersible resin of the present invention in water can be used as a water-based paint, an automobile paint, an electrodeposition paint, a plastic paint, a soil coating agent,
Useful as a heat-resistant coating agent, adhesive, etc. (Example) The present invention will be explained in more detail with reference to Examples.

Example 1 5 g of t-butanol-blocked methacryloyl isocyanate, 2.3 g of methacrylic acid, 7.89 g of n-butyl acrylate, and 1.5 Li of styrene were added to 25 g of dioxane.
g and heat to 100°C to dissolve. 2.
2°-Azobis(2,4-dimethylvaleronitrile)5
A solution of 80R9 in butyl acetate 109 was added dropwise. after that,
By aging for 2 hours, Mn=5500, Mw-1
1 piece of 2700 polymer was obtained.

Polymerization rate: 87.6%. 51.6 g of the obtained mixture containing 14.59 of the polymer was added to 209 of water, and triethylamine 3
By neutralizing with 9, a homogeneous aqueous dispersion was obtained at room temperature.

Example 2 N,N-dimethylaminoethyl methacrylate 39,
3 g of t-butanol blocked methacryloyl isocyanate, 4.59 g of methyl methacrylate and n
- Add 5.59 g of butyl acrylate to 25 g of butyl acetate and heat to about 90° C. to dissolve. 2.2゛-
Azobis(2,4-dimethylvaleronitrile) 4801
A butyl acetate/109 solution of No. 9 was added dropwise over about 1 hour.

Thereafter, by aging for 2 hours, a copolymer with Mn=4600 was obtained. Polymerization rate: 85%. Obtained polymer 13.
After removing the solvent from the mixture containing 69 under reduced pressure, 1 acetic acid was added.

Neutralization with 89 and addition of water gave an aqueous dispersion stable at room temperature.

Example 3 12.5 g of N,N-dimethylaminoethanol blocked methacryloyl isocyanate, 12.59 g of ethyl acrylate, 5.0 g of methyl methacrylate, 5.09 g of styrene and 15.09 g of ethyl hequinyl acrylate.
is added to butyl acetate 559 and heated to about 100°C to dissolve. A solution of 20 g of butyl acetate containing 1.59 g of 2,2'-azohisisobutyronitrile was added dropwise to this over about 1 hour. After that, by aging for about 3 hours, Mn=8,
A copolymer of 700 was obtained. Polymerization rate: 85%. Water was added to the obtained polymer, and hydroxyl group-containing polycarboxylic acid (methyl methacrylate/ethyl acrylate/acrylic acid/hydroquine ethyl methacrylate-2987=11.
The mixture was neutralized with a polymer having a polymerization ratio of 3/10.3/18.6 (hydroxyl value: 80; acid value: 80) to obtain an aqueous dispersion that was extremely stable at room temperature.

Examples 4-19 Polymers and neutralized aqueous dispersions of the polymers were produced in the same manner as in Examples 1-2 above. Table 1 shows the reaction conditions, polymerization rate, molecular weight of the produced polymer, and water dispersibility of the neutralized polymer. However, the abbreviations in the table have the following colors:
BMAI, methacryloyl isocyanate blocked with the corresponding blocking agent, ST, styrene:MM8,
Methyl methacrylate NBA, n-butyl acrylate: EA, ethyl acrylate; EIIA, ethyl hequinyl acrylate; ABDV, 2,2"-azopis(2,4-dimethylvaleronitrile), heIBN, 2.
2°-Azobisisobutyronitrile; Hosmer M.

CH30 CH2= CCOCHt CHt OP OH;0
0H TBAS.

CH3CH3 CIL=C-C-NH-C-CHtSO5H;0
CH3 T B A E MA.

CH3 CH2=CC0Cf(tcHtNHC(CH3)3 Note that ◯ in water dispersibility indicates that the dispersion state at room temperature is good.

Claims (1)

[Claims] 1. Formula in the main chain consisting of carbon-carbon bonds: ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, B is a hydrogen atom that participated in the addition reaction with the isocyanate group from the blocking agent Residues excluded are shown. ] The blocked isocyanatocarbonyl group represented by 1
Blocked isocyanatocarbonyl group-containing polymers having a molecular weight of 1,000 to 100,000, with a molecular weight of 1,000 to 100,000, to which 1 to 90% by weight (by weight of the polymer) of acidic or basic groups are bound (based on the weight of the polymer) ,
0.1-100% of the acidic or basic groups are neutralized. ) water-dispersible resin. 2. Formulas: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R represents a hydrogen atom or a lower alkyl group, and B
indicates a residue obtained by removing the hydrogen atom involved in the addition reaction with the isocyanate group from the blocking agent. ] After polymerizing the blocked acylisocyanate compound represented by the formula, an ethylenically unsaturated compound containing an acidic group or a basic group, and other polymerizable monomers as necessary, the acidic group or basic group in the resulting polymer is polymerized. The water-dispersible resin according to claim 1 obtained by neutralization. 3. Claim 1 in which the acidic group or basic group is a carboxylic acid group, sulfonic acid group, phosphoric acid group or amino group
The water-dispersible resin according to item 1 or 2.