JP2623206B2 - Pigment dispersant - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a pigment dispersant.
More specifically, pigments for paints that can be used in a wide range of paint resins such as room temperature drying alkyd, alkyd melamine, acrylic lacquer, acrylic melamine, acrylic urethane, vinyl acetate-acrylic, nitrified cotton lacquer, epoxy and urethane. It relates to a dispersant.

[0002]

2. Description of the Related Art Conventionally, a paint or the like containing a pigment is prepared by mixing a pigment and a dispersing resin to prepare a pigment dispersion for a primary color paint (pigment masterbatch), and then using the same resin as that used for the dispersion. It is diluted and commercialized. This is because when the pigment dispersing resin used for each pigment masterbatch and the resin used for dilution are different from each other, generally, the compatibility between the resins is poor, and the gloss and hardness of the coating film surface are reduced. Therefore, development of a pigment dispersing resin which has excellent compatibility with many kinds of paint resins and can be commonly used for various resin paints has been desired. For this purpose, a urethane-modified polyester resin is used as a pigment-dispersing resin (Japanese Unexamined Patent Publication No.
No. 91115), a copolymer using butyl methacrylate and a specific nitrogen-containing monomer as a resin for dispersing a pigment (Japanese Patent Laid-Open No. 60-139713), and having 1 carbon atom.
-4 alkyl (meth) acrylates and 6 to 3 carbon atoms
Using a copolymer comprising a compound having an aliphatic group of 0 and a polymerizable double bond in the molecule (Japanese Patent Application No. 4-233093).
No.) has been proposed.

[0003]

However, the above-mentioned urethane-modified polyester resin has good compatibility with a relatively wide range of coating resins, but has insufficient weather resistance due to its urethane bond. There is a problem that it cannot be used for paints that require weather resistance (paints for exteriors, etc.). Copolymers of butyl methacrylate and a specific nitrogen-containing monomer are types of paint resins that show compatibility. Is limited, so that it cannot be used for a wide range of coating resins. The number of carbon atoms is 1 to 4
A copolymer comprising an alkyl (meth) acrylate of the formula (I) and a compound having an aliphatic group having 6 to 30 carbon atoms and a polymerizable double bond in the molecule is compatible with a wide range of paint resins and has good properties. Although it provides excellent paint properties and is almost satisfactory as a pigment dispersing resin, when it is used for non-crosslinking paints such as acrylic lacquer, there is a problem that the alcohol resistance is insufficient.

[0004]

The present inventors have found that they have good compatibility with a very wide range of paint resins and, when mixed with each resin, include weather resistance and alcohol resistance. As a result of intensive studies on a pigment dispersing resin that does not impair the original performance of each resin paint, the present invention has been reached.

That is, the present invention relates to a (meth) acrylate (A) having an alkyl group having 1 to 4 carbon atoms,
A pigment dispersant comprising a copolymer (P) of (meth) acrylate (B) having an alkyl group of from 30 to 30 and the following monomer (C). Monomer (C);
(Meth) acrylic acid ester of compound (c5) obtained by adding alkylene oxide (c4) to compound (c3) obtained by reacting phenols (c1) with styrenes (c2).

In the present invention, the (meth) acrylate (A) having an alkyl group having 1 to 4 carbon atoms includes, for example, methyl (meth) acrylate, ethyl (meth) acrylate, 1-propyl (meth) acrylate, isopropyl Examples thereof include (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, and a mixture of two or more of these.

Of these, those which increase the glass transition point of the polymer, ie, methyl (meth) acrylate, ethyl methacrylate, isobutyl methacrylate and t-butyl ( (Meth) acrylate is preferred, and methyl methacrylate and t-butyl methacrylate are particularly preferred.

As (B), for example, hexyl (meth)
Acrylate, cyclohexyl (meth) acrylate,
Octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate,
Decyl (meth) acrylate, dodecyl (meth) acrylate, tridecyl (meth) acrylate, tetradecyl (meth) acrylate, 1-methyltridecyl (meth) acrylate, hexadecyl (meth) acrylate
Octadecyl (meth) acrylate, eicosyl (meth) acrylate, docosyl (meth) acrylate
And tetracosyl (meth) acrylate, triacontyl (meth) acrylate and a mixture of two or more thereof.

Of these, hexyl (meth) acrylic acid is preferred in order to be compatible with various resins for coatings and not to impair the original performance of each resin, including weather resistance, when mixed with each resin. G, cyclohexyl (meth) acryle
G, octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate
And decyl (meth) acrylate and dodecyl (meth) acrylate are preferred.

The monomer (C) is a compound (c3) obtained by reacting a phenol (c1) with a styrene (c2).
(Meth) acrylic acid ester of compound (c5) obtained by adding alkylene oxide (c4) to the above.

The phenols (c1) include phenol
And alkyl phenol, allyl phenol and aralkyl phenol. The alkyl group of the alkyl phenol generally has 1 to 20, preferably 1 to 12, carbon atoms. Specific examples of the alkyl phenol include cresol, butyl phenol, octyl phenol, and nonyl phenol. Examples of the allyl group of allylphenol include a phenyl group, a tolyl group, a xylyl group, a biphenyl group, and a naphthyl group. Specific examples of the allylphenol include phenylphenol, biphenylphenol, and naphthylphenol. No. Examples of the aralkyl group of aralkylphenol include a benzyl group and a phenylethyl group. Specific examples of the aralkylphenol include benzylphenol and phenylethylphenol.

[0012] Of these, it is well compatible with various resins for paints, and when mixed with each resin, it has alcohol resistance,
Phenol, cresol, phenylphenol and a mixture of two or more of these are preferred in order not to impair the original performance of each resin including weather resistance.

As the styrenes (c2), styrene,
α-methylstyrene, vinyltoluene and a mixture of two or more thereof.

The compound (c3) is a compound obtained by subjecting the above-mentioned phenols (c1) and styrenes (c2) to a Freedell-Crafts reaction. For example, 1 mol of phenols and 1 mol of styrene And 0.5 to 8 moles of
It is obtained by reacting at a temperature of 110 to 140 ° C. in the presence of an acidic catalyst such as a Lewis acid. The (c3) includes:
In addition to those obtained by adding styrenes to the benzene nucleus of phenols, those obtained by adding styrenes to the benzene nucleus of styrenes once added, only the styrenes are polymerized first, and the polymer is converted to phenol Benzene nuclei or styrenes once added to the benzene nucleus. The preferred number of moles of styrene added per mole of phenols is 0.8 to 4 moles, more preferably 1 to 3 moles.

As the alkylene oxide (c4),
Examples include ethylene oxide, propylene oxide, butylene oxide and tetrahydrofuran. Compound (c5) can be prepared by a known method, for example, N 2
It can be obtained by (poly) addition at a temperature of 100 to 190 ° C. under pressure in the presence of an alkali catalyst such as aOH, KOH, Na, CH 3 ONa or the like. The addition mole number of the alkylene oxide is usually 1 to 10 mol, preferably 1 to 4 mol.

Particularly preferred as (c5) is a compound obtained by adding 1 to 4 moles of ethylene oxide to a reaction product of 1 mole of phenol and 1 to 3 moles of styrene.

The monomer (C) is composed of the above (c5) and (meth)
Obtained by an esterification reaction with acrylic acid. As a method of esterification, a known method, for example, a method using a mineral acid such as sulfuric acid or hydrochloric acid, an organic acid such as aromatic sulfonic acid, or a Lewis acid catalyst such as boron fluoride ether; A method using an organic metal catalyst such as tin octylate; a method using an acidic ion exchange resin as a catalyst; a method using a drying agent such as anhydrous magnesium sulfate; a method using a dehydrating agent such as N, N′-dicyclohexylcarbodiimide; And combinations of the above methods.

The monomer constituting the copolymer (P) contains, if necessary, other polymerizable monomers (D) in addition to the above (A), (B) and (C). Also good.

(D) is not particularly limited as long as it can be copolymerized with (A), (B) and (C).
(Meth) acrylates other than (A), (B) and (C) [pentyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, (meth) acrylamide, trimethylamine (meth) acrylimide, (Meth) acryloyloxyethyltrimethylammonium chloride, benzyl (meth) acrylate, dibromopropyl (meth) acrylate, isobornyl (meth)
Acrylate, tetrahydrofurfuryl (meth) acrylate, allyl methacrylate, dicyclopentenyl (meth) acrylate, dicyclopentanyl (meth) acrylate, glycidyl (meth) acrylate, ( (Meth) acryloxyethyl phosphate, hydroxyethyl (meth) acrylate, glycerol (meth) acrylate, caprolactone-modified 2-hydroxyethyl (meth) acrylate, 2-perfluorooctylethyl ( (Meth) acrylate, (meth) acrylsulfoethyl and its salts, γ- (meth) acryloxypropyltri (trimethylsiloxy) silane, one-terminal (meth) acryloyl group-modified dimethylsiloxane, etc.); α, β unsaturated Carboxylic acids [(meth) acrylic acid, (anhydride) maleic acid, itaconic acid, etc.]; Alkenyl aromatic compounds (styrene, vinyl toluene, alpha-methyl styrene, etc.); vinyl chloride, vinyl carboxylate, dienes (butadiene, dicyclopentadiene, isoprene, etc.); N-
Vinylpyrrolidone and mixtures of two or more thereof.

When (D) is used, the amount used is usually 40% by weight or less based on all the monomers constituting the copolymer (P).

The weight ratio of (A) :( B) in the copolymer (P) is usually (30-95) :( 5-70), preferably (45-90) :( 10-55). . If the ratio of (A) is less than 30, the compatibility with an acrylic resin, particularly an acrylic resin containing vinyl acetate, becomes insufficient.
When it exceeds, the compatibility with the alkyd resin is extremely reduced. The weight ratio of (A + B) :( C) is usually (40
To 98): (2 to 60), preferably (60 to 95):
(5-40). If the ratio of (C) is less than 2, the alcohol resistance when used in a lacquer type paint will be insufficient, and if it exceeds 60, the compatibility with vinyl acetate-acrylic resin will be extremely reduced.

Gel permeer of copolymer (P) of the present invention
The number-average molecular weight determined by chromatography (GPC) is usually 1,000 to 10,000, preferably 1,
500-8,000. Number average molecular weight is 1,000
If it is less than 10%, the coating film properties of the coating will be reduced. If it exceeds 10,000, the compatibility with various coating resins will be reduced.

The method for producing the copolymer (P) is not particularly limited. For example, a monomer mixture comprising (A), (B), (C) and, if necessary, (D) is prepared by known thermal polymerization. It can be produced by polymerizing in a bulk or solution state by a radical polymerization method such as photopolymerization or radiation polymerization. A preferred polymerization method is a radical solution polymerization method using a radical initiator in an organic solvent.

In the case of solution polymerization, examples of the organic solvent used include aromatic hydrocarbons such as toluene and xylene;
Aliphatic hydrocarbons such as heptane and mineral spirits;
Esters such as ethyl acetate and butyl acetate; ketones such as methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; butyl cellosolve, butyl carbitol;
Ethers such as ethylene glycol dimethyl ether;
Alcohols such as isopropanol, n-butanol and t-butanol; and a mixture of two or more thereof. Among these, preferred solvents are toluene, xylene, methyl isobutyl ketone and butyl acetate alone or a mixture thereof.

When the radical polymerization reaction is carried out, known polymerization initiators can be used. Specific examples thereof include azo-based initiators such as azobisisobutyronitrile and azobisisovaleronitrile, and t-butyl peroxybenzoate. −
Peroxides such as t-butyl peroxyisobutyrate, di-t-butyl peroxide, hydrogen peroxide and the like can be mentioned. Of these, preferred are azobisisobutyronitrile, t-butyl peroxybenzoate and t
-Butyl peroxyisobutyrate.

In the production of (P), a known chain transfer agent such as lauryl mercaptan or dibenzyl ether may be used if necessary.

The polymerization temperature in the production of (P) is usually 50
To 180 ° C., and the method of polymerization may be either batch or continuous polymerization.

The copolymer (P) in the present invention is particularly excellent in compatibility with an acrylic resin because the main chain skeleton is derived from an acrylic resin, and has an alkyd type because it has a long-chain alkyl group in a side chain. Especially excellent in compatibility with resin. That is, the main chain and the side chains have different SP values as a whole,
Because of the well-balanced comb structure, it has excellent compatibility with various coating resins. In addition, since a plurality of aromatic rings based on the monomer (C) are ubiquitously present in the side chain, alcohol resistance is reduced.
Since it is excellent in water resistance and has no groups that adversely affect weather resistance such as urethane groups, it can be used as a pigment dispersing resin for almost all coating resins.

The pigment dispersant of the present invention comprises a copolymer (P) as an essential component, and if necessary, an organic solvent, another resin for paint, or other known additives for paint (surfactant, fluidity adjusting agent). Agents, pigment dispersants, adhesion improvers, etc.).

The high-concentration pigment dispersion (pigment masterbatch) using the pigment dispersant of the present invention comprises a copolymer (P), a pigment and, if necessary, an organic solvent, another resin for a coating material, It can be obtained by blending additives and the like. The pigment concentration in this case varies depending on the type of the pigment, but is usually 10 to 60% by weight.

As the organic solvent, those exemplified as the solvent for the solution polymerization can be used.

Examples of the pigment include inorganic pigments (carbon black, iron oxide, titanium oxide, calcium carbonate, graphite, zinc white, navy blue, etc.) and organic pigments (nitroso pigments, nitro pigments, azo pigments, phthalocyanine pigments, etc.). ) And mixtures thereof.

The resin composition for pigment dispersion of the present invention or the pigment masterbatch for paint using the same can be prepared by using a conventional disperser such as a roll mill disperser, a sand grind mill disperser, a planetary mixer, a high speed disperser. It is obtained by mixing and dispersing in a usual manner using the above method.

[0034]

EXAMPLES The present invention will be further described with reference to the following examples, but the present invention is not limited to these examples. In the following, “part” indicates “part by weight” and “%” indicates “% by weight”.

Production Example 1 A flask equipped with a stirrer, condenser, thermometer and dropping pump was charged with 34 parts of phenol and 3.5 parts of acid activated clay, and heated to 110 ° C., followed by styrene 6
6 parts were added dropwise over 3 hours, and the reaction was further performed at 110 to 120 ° C for 1 hour. The reaction product was filtered using diatomaceous earth to obtain styrenated phenol. 82.8 parts of the obtained styrenated phenol was placed in an autoclave equipped with a stirrer and a thermometer, and 0.2 parts of potassium hydroxide was added to obtain 13 parts.
The temperature was raised to 5 ° C, 26.4 parts of ethylene oxide was injected, and the mixture was reacted at 135 to 160 ° C for 3 hours to obtain a styrenated phenol ethylene oxide (2 mol) adduct. 91 parts of the obtained styrenated phenol ethylene oxide (2 mol) adduct is put in a 1 L Erlenmeyer flask, and 200 parts of chloroform and 51.5 parts of N, N'-dicyclohexylcarbodiimide are added and dissolved. , And 0.06 parts of dimethylaminopyridine was added.
21.5 parts of methacrylic acid were gradually added dropwise while maintaining the temperature at 0 ° C., and after the completion of the addition, the reaction was maintained at the same temperature for 10 hours to complete the reaction. Next, urea produced as a by-product was filtered off and chloroform was distilled off to obtain a methacrylic acid ester (C1) of a styrenated phenol ethylene oxide (2 mol) adduct.

Production Example 2 A flask equipped with a stirrer, a condenser, a thermometer, and a dropping pump was charged with 61.2 parts of p-phenylphenol and 3.5 parts of acid activated clay, and heated to 110 ° C. 85 parts of α-methylstyrene was added dropwise over 3 hours, and 1
The reaction was further performed at 10 to 120 ° C for 1 hour. The reaction product was filtered using diatomaceous earth to obtain α-methylstyrenated phenylphenol. 101.5 parts of the obtained α-methylstyrenated phenylphenol was put into an autoclave equipped with a stirrer and a thermometer, and 0.2 parts of potassium hydroxide was added to the autoclave.
C., and press-fit 33 parts of ethylene oxide.
The reaction was carried out at 5 to 160 ° C. for 3 hours to obtain an adduct of α-methylstyrenated phenylphenol ethylene oxide (3 mol). The obtained α-methylstyrenated phenylpheno-
134.5 parts of ethylene oxide (3 mol) adduct was placed in a 1 L Erlenmeyer flask, and 200 parts of chloroform and 51.5 parts of N, N'-dicyclohexylcarbodiimide were added.
The mixture was cooled to 2 ° C, 0.06 parts of dimethylaminopyridine was added, and 21.5 parts of methacrylic acid was gradually added dropwise while maintaining the liquid temperature at 0 to 5 ° C. After completion of the dropwise addition, the liquid temperature was maintained at the same temperature for 10 hours to complete the reaction. Then
After filtration of the by-produced urea, chloroform was distilled off to obtain methacrylic acid ester (C2) of α-methylstyrenated phenylphenol ethylene oxide (3 mol) adduct.

Example 1 30 parts of butyl acetate and 70 parts of xylene were placed in a flask equipped with a stirrer, a condenser, a thermometer, an inert gas inlet tube and a dropping pump, an inert gas was introduced, and butyl acetate was refluxed ( (Temperature: 125 to 128 ° C.) After stirring, 56 parts of methyl methacrylate, 7 parts of dodecyl methacrylate, 4 parts of (C1) obtained in Production Example 1, and styrene 23 were stirred.
Part, methacrylic acid 1 part, hydroxyethyl methacrylate 8 parts, dimethylaminoethyl methacrylate 1
, A mixture of 5 parts of azobisisobutyronitrile and 1 part of laurylmercaptan was added dropwise over 3 hours. After the completion of the addition, 5 parts of azobisisobutyronitrile was added, and the mixture was further reacted at the same temperature for 2 hours. Resin solution 1 having a non-volatile content of 50% and a number average molecular weight of 3,600 (by GPC; the same applies hereinafter)
I got

Example 2 Into a flask equipped with a stirrer, a condenser, a thermometer, an inert gas inlet tube and a dropping pump, 100 parts of xylene was introduced, an inert gas was introduced, the temperature was raised to 135 ° C., and the mixture was stirred.
50 parts of methyl methacrylate, 6.5 parts of methyl acrylate, 5 parts of t-butyl methacrylate, 12 parts of octyl methacrylate, (C2) 3 obtained in Production Example 2
, 15 parts of styrene, 0.5 parts of acrylic acid, 7 parts of hydroxyethyl methacrylate, 1 part of diethylaminoethyl methacrylate, and 8 parts of t-butyl peroxybenzoate were added dropwise over 3 hours. 4 parts of t-butyl peroxybenzoate was added over 1.5 hours, and the mixture was further reacted at the same temperature for 1 hour.
A resin solution 2 having a number average molecular weight of 3,200 was obtained.

Example 3 30 parts of methyl isobutyl ketone and 70 parts of xylene were charged into a flask equipped with a stirrer, a condenser, a thermometer, an inert gas inlet tube and a dropping pump, and an inert gas was introduced. Reflux (temperature; 114-
118 ° C.), and then, with stirring, methyl methacrylate 30
Parts, 29.5 parts of methyl acrylate, 10 parts of octyl methacrylate, 3 parts of (C1) obtained in Production Example 1, caprolactone-modified 2-hydroxyethyl methacrylate [Placel FM-2, Daicel Chemical Industries, Ltd. 8 parts,
0.5 parts of maleic anhydride, 3 parts of hydroxyethyl acrylate, 2 parts of dimethylaminoethyl methacrylate,
A mixture of 11 parts of styrene, 3 parts of cyclohexyl methacrylate and 5 parts of t-butyl peroxyisobutyrate was added dropwise over 3 hours, and after completion of the addition, 2.5 parts of t-butyl peroxyisobutyrate was added to 1.5 parts. The reaction was continued for 1 hour at the same temperature to obtain a resin solution 3 having a nonvolatile content of 50% and a number average molecular weight of 4,400.

COMPARATIVE EXAMPLE 1 The same procedure as in Example 1 was repeated except that the same amount of styrene was used instead of (C1) in Example 1.
%, A resin solution 4 having a number average molecular weight of 3,700 was obtained.

Comparative Example 2 A flask equipped with a stirrer, a condenser, a thermometer, an inert gas introduction tube and a dropping pump was charged with 60 parts of xylene, an inert gas was introduced, the temperature was raised to 100 ° C., and butyl was stirred. A mixture consisting of 98 parts of methacrylate, 2 parts of t-butylaminoethyl methacrylate and 1 part of azobisisobutyronitrile was added dropwise over 4 hours, and after the addition was completed, 1 part of azobisisobutyronitrile was added. The mixture was further reacted at the same temperature for 1 hour. Then, 40 parts of xylene was added, and a resin solution 5 having a nonvolatile content of 50% and a number average molecular weight of 18,000 was added.
I got

Performance Test 1 The six types of paint varnishes shown in Table 1 and the resin solutions 1 to 5 obtained in Examples 1 to 3 and Comparative Examples 1 and 2 had a resin solid content weight ratio of 7/3. The resulting mixture was applied to a glass plate and dried, and the coating film obtained was visually observed for the presence or absence of stain. A transparent sample was represented by ○ (pass), and a cloudy one was represented by × (fail). Table 1 shows the results.

[0043]

[Table 1]

1) 60% oil length soybean oil-modified pentaerythritol / phthalic acid varnish (nonvolatile content 60%) 2) Melamine resin varnish [Melan # 28 manufactured by Hitachi Chemical Co., Ltd.] and oil length 30
% Soybean oil-modified trimethylol cellulose / phthalic acid varnish 2
/ 8 mixed varnish (non-volatile content 50%) 3) Melamine resin varnish [Melan # 28 manufactured by Hitachi Chemical Co., Ltd.] and acrylic resin A (methyl methacrylate 60 parts, butyl acrylate 28 parts, human peroxyethyl acrylate 10 parts and acrylic Mixed varnish with 2/8 solids weight ratio with copolymer based on monomer composition of acid 2 parts, number average molecular weight 15,000 (non-volatile content 50%) 4) Styrene 30 parts, methyl methacrylate 30 parts, butyl acrylate 40 parts Toluene solution (number-average molecular weight: 22,000) in toluene solution (non-volatile content: 50%) based on the monomer composition of 5) Copolymer (number-average molecular weight) based on the monomer composition of 60 parts of vinyl acetate, 39 parts of methyl methacrylate, and 1 part of methacrylic acid 18,000) Toluene solution (non-volatile content 50%) 6) 70 parts of nitrified cotton solution, 27 parts of castor oil, glycerin, phthalic varnish, 3 parts of butyl phthalate toluene / vinegar Ethyl (5/5) solution (nonvolatile content 50%)

Performance Test 2 Mixing of the acrylic lacquer, vinyl acetate acrylic lacquer and nitrified cotton lacquer used in Performance Test 1 with the resin solutions 1 to 5 obtained in Examples 1 to 3 and Comparative Examples 1 and 2. The solution was applied on a glass plate and dried, and the surface of the obtained coating film was rubbed 20 times with absorbent cotton impregnated with methanol, and the presence or absence of turbidity of the coating film was visually observed. ○ (pass) a transparent thing,
Those with turbidity were represented by x (fail). Table 2 shows the results.

[0046]

[Table 2]

Examples 4 to 6 and Comparative Examples 3 and 4 Resin solutions 1 and 2 obtained in Examples 1 to 3 and Comparative Examples 1 and 2
5 20 parts each, titanium oxide 60 parts, xylene 10
Parts, propylene glycol monomethyl ether monoacetate (hereinafter abbreviated as MPA) 10 parts were mixed and dispersed by a sand grind mill until the particle size became 10 μm or less, and pigment master batches [1] to [5] were dispersed. Prepared.

Performance Test 3 Two types of varnishes for melamine paints (melamine / alkyd varnish and melamine / acrylic varnish) used in performance test 1 and pigment master batches obtained in Examples 4 to 6 and Comparative Examples 3 and 4. [1] to [5] were mixed such that the resin solid content weight ratio was 8/2 to obtain white paints A1 to A5 from melamine / alkyd varnish and white paints B1 to B2 from melamine / acryl varnish. . After diluting each white paint with a mixed thinner, this paint was applied to a treated steel sheet to a dry film thickness of 30μ.
m and sprayed at 140 ° C. for 20 minutes to evaluate the coating film performance. Table 3 shows the results.
Shown in

[0049]

[Table 3]

1) JIS K-5400 67; 60-degree specular reflectivity 2) JIS K-5400 614; use Mitsubishi Uni pencil 3) JIS K-5400 615; Cut 100 squares of 1 mm square and use cellophane tape The number is shown by the number of squares remaining after being pressed and peeled.

[0051]

The pigment dispersant of the present invention is excellent in pigment dispersibility, shows good compatibility with various coating resins, and, when mixed with each resin, includes weather resistance and alcohol resistance.
Since it has characteristics that do not impair the original performance of each resin paint, it becomes possible to manufacture a pigment masterbatch that can be commonly used for various paint resins. Pigment masterbatch using the pigment dispersant of the present invention is a room temperature drying type alkyd paint, alkyd melamine paint, acrylic lacquer paint, acrylic melamine paint, vinyl acetate-based paint, nitrified cotton lacquer paint,
It can be used as a coloring agent for a very wide range of paints such as epoxy paints and urethane paints. As a result, the type of pigment masterbatch is greatly reduced, and paint productivity is improved.

 ──────────────────────────────────────────────────続 き Continuing from the front page Examiner Takeshi Sato (56) References JP-A-4-216878 (JP, A)

Claims (5)

(57) [Claims] 1. A (meth) acrylate having an alkyl group having 1 to 4 carbon atoms (A), a (meth) acrylate having an alkyl group having 6 to 30 carbon atoms (B) and a monomer (C) shown below: pigment dispersing agent characterized by comprising a copolymer (P). A monomer (C); a compound (c3) obtained by reacting a phenol (c1) with a styrene (c2);
Compound (c) to which alkylene oxide (c4) has been added
5) The (meth) acrylic ester. Wherein (C) is phenol 1 mole of pigment dispersing agent according to claim 1, wherein (meth) acrylic acid ester of ethylene oxide 1-4 moles adducts of reaction products of styrene 3 mol. 3. The weight ratio of (A) :( B) is (30 to 9).
5): (5 to 70), and (A + B) :( C) is (40 to 98) :( 2 to 60) by weight ratio.
Or pigment dispersants according. 4. The number average molecular weight of (P) is 1,000 to 1.
The pigment dispersion according to any one of claims 1 to 3, wherein the pigment dispersion is 0.000.
Agent . 5. The pigment dispersant according to claim 1, which is used in a non-aqueous system.