JPH0465088B2 - - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a dispersion stabilizer composition with excellent dispersibility, which is used when producing a urethane powder polymer by a non-aqueous emulsion polymerization method.

[Conventional technology]

Regarding the method for producing polyurethane powder by non-aqueous emulsion polymerization, the basic polymerization method has already been explained by Matsumoto et al. (Journal of Japan Adhesive Association, 9 , 183, 1973). Further, Japanese Patent Publication No. 57-29485 describes a method for producing polyurethane powder by a non-aqueous emulsion polymerization method. The most important point in this polymerization method is the selection of a dispersion stabilizer. In Japanese Patent Publication No. 57-29485, a copolymer of a monomer having a long chain alkyl such as lauryl methacrylate and a monomer such as methyl methacrylate or acrylamide is used as a dispersant. This dispersant is emulsifiable in non-polar solvents such as n-hexane only for mixtures of polyol and chain extender, but has no dispersing ability for mixtures or some reactants of polyol, chain extender and polyisocyanate. It has the disadvantage that a good emulsification state cannot be obtained. It has been desired to develop a dispersion stabilizer with excellent dispersion performance to solve this problem.

[Problem that the invention seeks to solve]

As a result of intensive research and consideration on dispersion stabilizers to improve dispersion performance, which is a drawback of conventional methods, the present inventor used a dispersion stabilizer consisting of a compound having a hydroxyl group, alkoxy polyethylene propylene glycol, and polyisocyanate. The inventors have discovered that improvements can be made by doing this, leading to the present invention.

[Means for solving problems]

That is, the present invention comprises an ethylenically unsaturated monomer (A) having a side chain consisting of a hydrocarbon group having 6 or more carbon atoms and an ethylenically unsaturated monomer (B) having a hydroxyl group in a molar ratio of A. /B
Hydroxyl group-containing vinyl polymer (a) obtained by reacting within the range of 1/1 to 20/1, molecular weight
The present invention relates to a dispersion stabilizer composition for polyurethane, characterized by comprising a reaction product of 300 to 2000 alkoxy polyethylene propylene glycol (2) and polyisocyanate (3).

By adding the dispersion stabilizer of the present invention to a mixture of a polyol and a chain extender, or a mixture of a polyol, a chain extender, and a polyisocyanate, it can be stably emulsified in a nonpolar solvent. Furthermore, even if a mixture of a polyol, a chain extender, and a polyisocyanate to which the dispersion stabilizer of the present invention is added is subjected to an initial reaction and emulsified in a nonpolar solvent, stable dispersion can be achieved.

Examples of the ethylenically unsaturated monomer (A) having a side chain consisting of a hydrocarbon group having 6 or more carbon atoms used in the production of the dispersion stabilizer in the present invention include, for example, 1-
octene, 1- or 2-nonene, 1- or 2
-decene, 1- or 2-heptadensene, 2-
Methyl-1-nonene, 2-methyl-1-decene,
aliphatic linear unsaturated hydrocarbons containing vinyl, propenyl or isopropenyl groups such as 2-methyl-1-dodecene, 2-methyl-1-hexadecene, 2-methyl-1-heptanedecene, acrylic acid or methacrylic acid; - Esters with aliphatic alcohols having 6 or more carbon atoms such as ethylhexyl alcohol and hexyl alcohol, or aliphatic alcohols having 6 or more carbon atoms such as cyclohexanol, norbonanol, and adamantanol are used.

As the ethylenically unsaturated monomer (B) having a hydroxyl group used in the production of the dispersion stabilizer, allyl alcohol, 3-buten-1-ol, 4-
or 3-penten-1-ol, 5- or 4
-hexen-1-ol, 6- or 5-hepten-1-ol, 7- or 6-octen-1-
ol, 8- or 7-nonen-1-ol, 2
-Methyl allyl alcohol, 3-methyl-3-buten-1-ol, 4-methyl-4-pentene-
1-ol, 5-methyl-5-hexen-1-ol, 6-methyl-hepten-1-ol, 7-
Aliphatic unsaturated alcohols such as methyl-7-octen-1-ol, 8-methyl-8-nonen-1-ol, acrylic or methacrylic acid and ethylene glycol, 1,2- or 1,3-propanediol, Monoesters with 1,3- or 1,4-butanediol are used.

These ethylenically unsaturated monomers (A) and (B) are obtained as random copolymers, block copolymers or graft copolymers. The polymerization method is not particularly limited, and a conventional polymerization method of ethylenic monomers using a radical initiator as a reaction initiator can be used. The molar ratio of (A) and (B) is preferably in the range of 1/1 to 20/1. If it exceeds 20/1, the affinity for non-polar solvents will become stronger and the dispersion performance will deteriorate, although this will depend on the molecular weight of the alkoxypolyethylene propylene glycol to be reacted later. If it is less than 1/1, the solubility in nonpolar solvents will be poor and the effect as a dispersion stabilizer will not be exhibited.

Alkoxypolyethylene propylene glycol (b) used in the production of a dispersion stabilizer is a compound obtained by adding ethylene oxide and propylene oxide to a monofunctional alcohol such as methanol. The molar ratio of ethylene oxide and propylene oxide is preferably in the range of 1/1 to 1/0, and the molecular weight of the alkoxypolyethylene propylene glycol is preferably in the range of 300 to 2,000. When the molecular weight is less than 300, the dispersion stabilizer has a weak affinity for the polyurethane composition, resulting in poor dispersibility. If the molecular weight exceeds 2000, the polarity balance of the dispersion stabilizer will be lost, depending on the type and amount of the hydroxyl group-containing vinyl polymer to be reacted, and the effect as a dispersion stabilizer will be lost. The monofunctional alcohol used preferably has a molecular weight of 100 or less.

Examples of the polyisocyanate (c) used in the production of the dispersion stabilizer include aromatic diisocyanates such as tolylene diisocyanate, xylylene diisocyanate, 4,4'-diphenylmethane diisocyanate, 1,6-hexamethylene diisocyanate, 1, These include aliphatic diisocyanates such as 12-dodecane diisocyanate, and alicyclic diisocyanates such as cyclohexane 1,4-diisocyanate and isophorone diisocyanate.

The reaction of the hydroxyl group-containing vinyl polymer (a), the alkoxypolyethylene propylene glycol (b), and the polyisocyanate (c) is carried out in the same manner as the usual urethanization reaction, but a two-step reaction method is preferred. That is, in the first stage, the alkoxypolyethylene propylene glycol and polyisocyanate are reacted in equimolar amounts, and then in the second stage, the reaction product obtained in the first stage is reacted with the hydroxyl group-containing vinyl polymer.
A method can be adopted in which the reaction is carried out at a molar ratio of NCO/OH in the range of 1/1 to 1/10.

The dispersion stabilizer thus obtained has a structure in which a vinyl polymer is used as the main chain, and a hydrocarbon group having 6 or more carbon atoms and an alkoxy polyethylene propylene glycol polyisocyanate adduct are attached as side chains. This hydrocarbon group having 6 or more carbon atoms has an affinity for nonpolar solvents, and the alkoxypolyethylene propylene glycol polyisocyanate adduct and unreacted hydroxyl group have an affinity for the polyurethane composition, and these balance to form a dispersion stabilizer. It acts as.

The reactions of compounds (a), (b) and (c) of the present invention can be carried out in a solvent used in the urethanization reaction. Further, a known catalyst can be used as a reaction catalyst. These catalysts include commonly used catalysts such as dibutyltin dilaurate, stannous octoate, tertiary amines such as N-methylmorpholine and triethylamine, lead naphthenate, lead octoate, and the like.

The dispersion stabilizer for polyurethane of the present invention can be used as an additive when producing polyurethane using a non-aqueous emulsion polymerization method. The polyurethane may be a normal flame plastic polyurethane resin, an incomplete flame plastic polyurethane resin containing an isocyanate group or a blocked isocyanate group as required, or a thermosetting polyurethane resin.

The polyols constituting these polyurethanes include all compounds having at least two active hydrogen-containing groups. Examples include polyester polyols, polyalkylene ether glycols, polytetramethylene ether glycols, and mixtures thereof.

Furthermore, as the chain extender constituting the polyurethane, those containing at least two active hydrogen groups per molecule and having a molecular weight of about 60 to about 300 can be used.

As the polyisocyanate constituting the polyurethane, compounds having at least two isocyanate groups can be used alone or in a mixture. Examples suitable for use include the compounds listed above as examples of polyisocyanates used in the preparation of dispersion stabilizers. In addition, isocyanate group-terminated compounds, carbodiimidization reactions, etc. by reaction of these compounds with active hydrogen-containing compounds,
Polyisocyanates such as isocyanate modified products obtained by isocyanurate reaction and phosgenated condensates of analine and formaldehyde can also be used. Also, methanol, n-,
Polyisocyanates partially or completely stabilized with a suitable blocking agent having one active hydrogen in the molecule, such as butanol, benzyl alcohol, ε-caprolactam, methyl ethyl ketone oxime, phenol, and cresol, can be used.

The content of the polyol, chain extender and polyisocyanate for producing polyurethane cannot be limited as it varies depending on the purpose of use of the polyurethane, but the molar ratio of the chain extender and polyol is usually in the range of 1/10 to 5/1. Preferably, chain extenders may not be used in some cases. In addition, the molar ratio of the isocyanate groups of polyisocyanate to the active hydrogen groups of polyol and chain extender is usually 1.5.
A range of 0.8 to 0.8 is preferable. The amount of dispersion stabilizer used in the production of these polyurethanes is 1 to 20% by weight based on the polyurethane.

The basic technology of the non-aqueous emulsion polymerization method is disclosed in Japanese Patent Publication No. 44-30736, and its application to polyurethane is disclosed in Japanese Patent Publication No. 57-29485. To summarize, the non-aqueous emulsion polymerization method is a method in which monomers are polymerized using an organic liquid other than water as a medium, and the polymer is produced in the form of discontinuous particles using the organic medium as a continuous phase. In this case, a technique is used in which a dispersion stabilizer is added to produce a polymer in a stable state, and the selection of the dispersion stabilizer is extremely important.

The organic medium used in the non-aqueous emulsion polymerization method is a non-aqueous organic liquid that is insoluble in the particulate polymer produced and has inert properties that do not inhibit the polymer reaction. In the present invention, for example, aliphatic or alicyclic hydrocarbons such as n-hexane, octane, dodecane, and liquid paraffin are used.
Considering the reaction temperature, those having a boiling point of 60°C or higher are preferred. These can be used alone or in combination of two or more.

The ratio of the non-aqueous organic liquid serving as the continuous phase to the polyurethane serving as the dispersed phase is preferably such that the amount of polyurethane is 10 to 80% by weight based on the total amount. From the viewpoint of production efficiency and cost, the content is particularly preferably 40% by weight or more.

The internal temperature at which polyurethane is produced by these nonaqueous emulsion methods is preferably 20 to 150°C.
Catalysts can also be used to increase the reaction rate and drive the reaction to completion. A variety of known catalysts can be used, including dibutyltin dilaurate, stannous octoate, tertiary amines such as N-methylmorpholine and triethylamine, lead naphthenate, lead octoate, and others. These catalysts are used in amounts necessary to provide catalytic action, preferably from about 0.01% to about 1% by weight, based on the polyurethane composition.

Any known emulsification equipment may be used to disperse the reactants consisting of the dispersion stabilizer, polyol, chain extender, and polyisocyanate in the non-aqueous organic liquid. In addition, for the reaction, all the raw materials may be introduced simultaneously, or may be introduced in stages depending on the purpose. As a stepwise preparation method, (1) Add nonaqueous organic liquid to the mixture of dispersion stabilizer, polyol, and chain extender, emulsify it, and prepare polyisocyanate. (2) Add nonaqueous organic liquid to the mixture of dispersion stabilizer, polyol, and polyisocyanate. Add a water-organic liquid to emulsify, then add a chain extender immediately or after the reaction has proceeded (3) React the polyol and polyisocyanate in advance to form a prepolymer, mix with a dispersion stabilizer, add a non-aqueous organic liquid and emulsify. However, there are other methods such as adding a chain extender. Although the catalyst may be added at any time, it is preferable to add the catalyst after the entire amount has been added.

The particulate polyurethane obtained in this way can contain active hydrogen such as methanol, ε-caprolactam, methyl ethyl ketone oxime, phenol, etc. in the molecule as necessary during or after the reaction.
It can be stabilized by adding a suitable blocking agent. The dispersion solution can be used as it is as a paint or adhesive.

The particulate polyurethane thus obtained can also be recovered from the dispersion solution by filtration or decantation and subsequent drying under normal pressure or reduced pressure. The obtained polyurethane powder is a non-agglomerated particle body with an average particle size ranging from 0.1 to 2000 μm and above. The powder can be used in a wide range of applications, including powder coatings, various molding material modifiers, and fillers.

〔Example〕

Next, the present invention will be explained in more detail with reference to Examples.

Example 1 (1) Synthesis of hydroxyl group-containing vinyl polymer 117 g of butyl acetate was placed in a four-necked flask equipped with a thermometer, stirrer, and condenser, and heated to 110°C while passing nitrogen gas. 2-ethylhexyl methacrylate
A mixture of 160.7 g (0.81 mol), 2-hydroxyethyl methacrylate 15.1 g (0.12 mol) and 7.0 g of benzoyl peroxide paste (benzoyl peroxide content 50% by weight) was added dropwise over 2 hours at the same temperature while stirring. did. The temperature was raised to 120°C and the mixture was reacted for 3 hours to obtain a hydroxyl group-containing vinyl polymer.

(2) Synthesis of dispersion stabilizer In a four-neck flask equipped with a thermometer, stirrer, and condenser, add 40.5 g of butyl acetate, 20.0 g (0.030 mol) of methoxypolyethylene glycol with a molecular weight of 670, and 5.2 g of 2,4-tolylene diisocyanate. g
(0.030 mol) and while passing nitrogen gas.
After heating to 80°C and reacting for 2 hours, 76.9g of the hydroxyl group-containing vinyl polymer obtained in (1)
(0.030 mol OH) and then heated to 80℃ for 1 hour.
dibutyltin dilaurate
0.01g was added and reacted for 3 hours at the same temperature to obtain a dispersion stabilizer.

(3) Synthesis of polyurethane powder (application example) 18.2 g of the dispersion stabilizer obtained in (2) was placed in a four-neck separable flask equipped with a thermometer, a propeller-type stirrer, and a cooler at 60°C. heated molecular weight
1000 polybutylene adipate 57.2g (0.057
mol), 1,4-butanediol 5.1g (0.057
molar) and mix evenly. After adding 28.6 g (0.114 mol) of diphenylmethane diisocyanate at 50°C and mixing uniformly, 91 g of Shellsol 71 (manufactured by Shell Chemical, paraffin with a boiling point of 170 to 200°C and the same below) was added and emulsified by stirring at high speed (approximately 800 rpm). let Next, 0.01g of diptyltin dilaurate was added, and the stirring speed was lowered (approx.
(500 rpm) for 1 hour at room temperature. The temperature was raised to 70°C and the mixture was reacted for 3 hours to obtain a particulate polyurethane polymer dispersed in Shellsol 71. This dispersion was allowed to stand, the supernatant liquid was removed by decantation, and the dispersion was dried under reduced pressure to obtain a polyurethane powder. This powder had a main particle size of about 10-100 μm.

Example 2 (1) Synthesis of hydroxyl group-containing vinyl polymer Shellsol 71 97.7 used in Example 1 (3) was used in a four-necked flask equipped with a thermometer, stirrer, and condenser.
g and heated to 120°C while passing nitrogen gas. Pre-prepared lauryl methacrylate 139.4 g (0.55 mol), 2-hydroxyethyl methacrylate 7.1 g (0.055 mol)
A mixture of 5.9 g of benzoyl peroxide paste (benzoyl peroxide content: 50% by weight) was added dropwise over 2 hours at the same temperature with stirring. 140
The temperature was raised to 0.degree. C. and the mixture was reacted for 4 hours to obtain a hydroxyl group-containing vinyl polymer.

(2) Synthesis of dispersion stabilizer In a four-neck flask equipped with a thermometer, stirrer, and condenser, add 29.3 g of toluene and 16.9 g of methoxypolyethylene propylene glycol (propylene oxide/ethylene oxide = 1/4 molar ratio) with a molecular weight of 1480. (0.011 mol), 2.0 g (0.011 mol) of 2,4-trirediisocyanate were charged, heated to 80°C while passing nitrogen gas, and reacted for 2 hours. 51.8 g (0.011 mol OH) of vinyl polymer was added and then reacted at 80° C. for 1 hour, 0.01 g of dibutyltin dilaurate was added and further reacted at the same temperature for 3 hours to obtain a dispersion stabilizer.

(3) Synthesis of polyurethane powder (application example) Dispersion stabilizer 9.3 obtained in Example 2 (2) was placed in a four-necked separable flask equipped with a thermometer, a propeller-type stirrer, and a cooler. g, polyethylene adipate with a molecular weight of 1000 heated to 60°C
59.6g (0.060mol), ethylene glycol 3.7g
(0.060 mol) and mix uniformly. 50℃
30.0g of diphenylmethane diisocyanate
(0.12 mol) and mixed uniformly, then IP Solvent 1620 (manufactured by Idemitsu Petrochemical, boiling point 170-200
Add 97.7 g of paraffin (at
800 rpm) Stir to emulsify. Next, 0.01 g of dibutyltin dilaurate was added, and the stirring speed was reduced (approximately 500 rpm) to allow reaction at room temperature for 1 hour. The temperature was raised to 80°C and the mixture was reacted for 3 hours to obtain a particulate poppyurethane polymer dispersed in the IP solvent. This dispersion was allowed to stand, the supernatant liquid was removed by decantation, and the dispersion was dried under reduced pressure to obtain a polyurethane powder. This powder had a main particle size of about 30-150 μm.

Example 3 (1) Synthesis of hydroxyl group-containing vinyl polymer Shell sol 71 97.7 used in Example 1 (3) in a four-necked flask equipped with a thermometer, stirrer, and condenser.
g and heated to 120°C while passing nitrogen gas. Pre-prepared lauryl methacrylate 125.2 g (0.49 mol), 2-hydroxyethyl methacrylate 21.3 g (0.16 mol)
A mixture of 5.7% and benzoyl peroxide paste (benzoyl peroxide content: 50% by weight) was added over 2 hours at the same temperature with stirring. 140
The temperature was raised to 0.degree. C. and the mixture was reacted for 4 hours to obtain a hydroxyl group-containing vinyl polymer.

(2) Synthesis of dispersion stabilizer In a four-necked flask equipped with a thermometer, stirrer, and condenser, add 29.3 g of toluene, 1/1 mole adduct of hexamethylene diisocyanate and methoxypolyethylene glycol with a molecular weight of 1500 (3 moles of hexamethylene diisocyanate) and 1 mol of methoxypolyethylene glycol, free hexamethylene diisocyanate was removed by distillation, NCO content 2.3%) 18.9%
(0.010 mol NCO) and 51.8 g of the hydroxyl group-containing vinyl polymer obtained in Example 3 (1)
(0.034 mol OH) was charged, heated to 80° C. while passing nitrogen gas, and reacted for 1 hour. Then, 0.02 g of dibutyltin dilaurate was added and further reacted at the same temperature for 4 hours to obtain a dispersion stabilizer.

(3) Synthesis of polyurethane powder (application example) Example 3 was placed in a four-necked separable flask equipped with a thermometer, a propeller-type stirrer, and a cooler.
18.2g of the dispersion stabilizer obtained in step (2), 67.3g of polyethylene adipate with a molecular weight of 2000 heated to 80℃
g (0.034 mol), 1,4-butanediol 6.1
g (0.068 mol) and mix uniformly.
Hexamethylene diisocyanate 17.5g
After adding (0.104 mol) and mixing uniformly, Shellsol
Add 90.9g of 71 and stir at high speed (approximately 800 rpm) to emulsify. Next, 0.03g of dibutyltin dilaurate was added, and the stirring speed was lowered (approx.
500 rpm) for 1 hour at room temperature. The temperature was raised to 90°C and the mixture was reacted for 5 hours to obtain a particulate polyurethane polymer dispersed in Shellsol 71. This dispersion was allowed to stand, the supernatant liquid was removed by decantation, and the dispersion was dried under reduced pressure to obtain a polyurethane powder. This powder had a main particle size of about 10-80 μm.

Comparative Example 1 (1) Synthesis of hydroxyl group-containing vinyl polymer In the same manner as in Example 1 (1), butyl acetate was placed in a flask.
117g was charged and heated to 110°C while passing nitrogen gas. 76.1 g (0.38 mol) of 2-ethylhexyl methacrylate prepared in advance, 2
-Hydroxyethyl methacrylate 99.7g
A mixture of (0.77 mol) and 7.0 g of benzoyl peroxide paste (benzoyl peroxide content: 50% by weight) was dropped over 2 hours at the same temperature with stirring. The temperature was raised to 120°C and the mixture was reacted for 3 hours to obtain a hydroxyl group-containing vinyl polymer.

(2) Synthesis of polyurethane powder Add butyl acetate to the same flask as in (2) of Example 1.
72.0g, methoxypolyethylene propylene glycol with a molecular weight of 1480 used in Example 2 (2) 51.9
(0.035 mol) and 6.1 g (0.035 mol) of 2,4-tolylene diisocyanate were heated to 80°C while passing nitrogen gas and reacted for 2 hours. 70.1 g (0.18 mol OH) of vinyl polymer was added thereto, followed by reaction at 80° C. for 1 hour, and 0.01 g of dibutyltin dilaurate was added, followed by further reaction at the same temperature for 3 hours to obtain a decomposition stabilizer.

(3) Synthesis of polyurethane powder (comparative application example) In a flask similar to (3) of Example 1, the composition of Comparative Example 1 was placed.
18.2g of the dispersion stabilizer obtained in (2), 57.2g of polybutylene adipate with a molecular weight of 1000 heated to 60℃
(0.057 mol), 1,4-butanediol 5.1g
(0.057 mol) and mix uniformly. 28.6 g of diphenylmethane diisocyanate at 50℃
After adding (0.114 mol) and mixing uniformly,
Add 91g of Shellsol 71 and increase the speed (approx. 800rpm)
Stirred. As a result, the reactant was not dispersed in Shellsol 71 and was in the form of a lump.

Comparative example 2 (1) Hydroxyl group-containing vinyl polymer The same material as in Example 1 (1) was used.

(2) Synthesis of dispersion stabilizer Add butyl acetate to the same flask as in (2) of Example 1.
69.6 g, 15.6 g (0.078 mol) of methoxypolyethylene glycol with a molecular weight of 200, and 13.6 g (0.078 mol) of 2,4-tolylene diisocyanate were charged, heated to 80°C while passing nitrogen gas, and reacted for 2 hours. 201.1g (0.078 mol OH) of the same hydroxyl group-containing vinyl polymer as in 1-(1)
and continue to react at 80℃ for 1 hour.
0.01 g of dibutyltin dilaurate was added and reacted at the same temperature for 3 hours to obtain a dispersion stabilizer.

(3) Synthesis of polyurethane powder (comparative application example) Emulsification was carried out in the same manner as in (3) of Example 1, except that the dispersion stabilizer obtained in (2) of Comparative Example 2 was used. As a result, the reactant is Shellsol 71
It was not dispersed and was lumpy.

Comparative Example 3 (1) Synthesis of dispersion stabilizer 97.7 g of Shellsol 71 used in Example 1 was placed in a four-necked flask equipped with a thermometer, stirrer, and condenser.
was charged and heated to 120°C while passing nitrogen gas. 119 g (0.47 mol) of lauryl methacrylate, 27.5 g (0.28 mol) of methyl methacrylate and benzoyl peroxide paste (benzoyl peroxide content 50% by weight) prepared in advance
5.9 g of the mixture was added dropwise over 2 hours at the same temperature while stirring. The temperature was raised to 140°C and the mixture was reacted for 4 hours to obtain a dispersion stabilizer.

(2) Synthesis of polyurethane powder Emulsification was carried out in the same manner as in (3) of Example 2, except that 9.3 g of (1) of Comparative Example 3 was used as a dispersion stabilizer. As a result, the reactant was poorly dispersed in the IP solvent and became lumpy.

〔Effect of the invention〕

The dispersion stabilizer composition for polyurethane obtained by the present invention has excellent dispersion performance in the production of polyurethane powder by a non-aqueous emulsion polymerization method.

Moreover, a polyurethane dispersion using the dispersion stabilizer composition of the present invention can be used as a coating material or adhesive as a dispersion solution.

Further, the urethane powder obtained using the dispersion stabilizer composition of the present invention has a wide range of uses such as powder coatings, various molding material modifiers, and fillers.

Claims (1)

[Claims] 1 An ethylenically unsaturated monomer (A) having a side chain consisting of a hydrocarbon group having 6 or more carbon atoms and an ethylenically unsaturated monomer (B) having a hydroxyl group at a molar ratio of A/
Reaction production of a vinyl polymer (a) with a hydroxyl group content obtained by reacting B in a range of 1/1 to 20/1, an alkoxy polyethylene propylene glycol (b) with a molecular weight of 300 to 2000, and a polyisocyanate (c) 1. A dispersion stabilizer composition for polyurethane, comprising: