JPS61192727A - Pigment composition and its production - Google Patents

Abstract

PURPOSE:To obtain a pigment composition which has stable and excellent properties, by adding a pigment to a phosphate triester having bonded polyester chains. CONSTITUTION:A pigment is treated by adding thereto phosphate ester compound of the formula and, if required, an organic solvent, a binder resin, a synthetic resin and a plasticizer. In the formula, -X is -A-R (wherein -A- is a selfcondensation polyester of a hydroxycarboxylic acid and is terminated with a carboxyl group or a group of ester with an alcohol), -Y- and -Z are each -A-R-, -B or -C (wherein -B is a carboxyl group or its ester group and -B is an alcohol residue). The MW of the polyester alcohol component used in said phosphate ester compound is preferably about 500-5,000. For example, a selfcondensation polyester of a hydroxycarboxylic acid, such as a polyester of a hydroxycarboxylic acid containing a 4-30 C hydrocarbon chain can be used.

Description

Detailed Description of the Invention (Field of Industrial Application) The present invention relates to a novel pigment composition and a method for producing the same. The object of the present invention is to provide an excellent method for producing coloring materials such as paints, printing inks, and synthetic resin colorants used as auxiliary agents, as well as to provide useful pigment compositions.

(Prior Art) Conventionally, in the production of paints and printing inks, dispersion aids have been used for dispersing pigments in paint vehicles and printing ink varnishes, and for dispersing pigments from aqueous filter cakes into oil vehicles and oil-based varnishes. For example, the phospholipid lecithin has been used as an agent or flushing aid.

(Problems to be solved by the invention) However, since lecithin is a natural phospholipid, it is susceptible to oxidation and rancidity, and there is a risk of deterioration and putrefaction. There was a need for compounds that could be used as agents or flushing aids.

In view of the above-mentioned defects in dispersion aids or flushing aids for pigments, the present inventors conducted various studies on compounds that have an affinity for various vehicles and varnishes, and also have an affinity for pigments. As a result, they discovered that a triester obtained by reacting a polyester chain having a hydroxyl group with phosphoric acid exhibits excellent properties and effects, and completed the present invention.

(Means for Solving the Problems) That is, the present invention provides a pigment composition containing a pigment and a dispersion aid, characterized in that the dispersion aid is a phosphoric acid ester compound represented by the following general formula. A pigment composition and a method for producing the same.

l X-0-P-0-Z - or -A-R in the dithermal formula group or ester group with alcohol), and -Y and -
Z is represented by -A-R1-B and -C (-B in the formula is a group of carboxylic acid or its ester, and -0 is a residue of alcohol).

To explain the present invention in detail, the dispersion aid used in the present invention and which mainly characterizes the present invention is a specific phosphoric triester compound.

The phosphoric acid ester compound used in the present invention can be obtained by reacting the corresponding polyester alcohol component and alcohol component with a conventionally known phosphorylating agent according to a conventionally known reaction method.

As the phosphorylating agent, conventionally known phosphorus oxychloride, phosphorus pentoxide, phosphorus trichloride, etc. are used. Phosphorus oxychloride is the most preferred phosphorylating agent.

When a halogenated phosphorus compound is used, it is preferable to use a basic catalyst, such as tertiary amines such as triethylamine, pyridine, 2,6-lutidine, 1,
Organic bases such as 8-diaza-bicyclo(5,4,O)undecene-7, and manifest and latent inorganic bases such as oxides, hydroxides, carbonates, and organic acid salts of alkali metals and alkaline earth metals. After one reaction, halides, salts, bases and other impurities are preferably removed by reaction, neutralization, washing with water, etc.

Regarding the reaction conditions, in the case of phosphorus oxychloride, the initial esterification reaction is preferably performed dropwise at a low temperature because the reaction is violent, and heating is preferred to complete the triester.

The alcohol component to be reacted is selected and used in various ways depending on the purpose of the product.

In addition to directly reacting the triester to obtain the desired product, the triester is first synthesized by reacting with, for example, methyl ester of 12-hydroxystearic acid, and then it is reacted with a polyester of 12-hydroxystearic acid to remove methanol. It can also be obtained by a reaction using a precursor, such as condensation with a polyester to synthesize a phosphotriester compound of the polyester.

The polyester alcohol components used are conventionally known hydroxyl group-containing aliphatic, alicyclic and aromatic polyesters.

The molecule ゛♀ of the polyester alcohol component to be used is not particularly restricted, but may be a dimer to average molecule #M1.
0,000 or less, preferably 500 to 5,000.

For example, the following are used.

(A) A self-condensing polyester of hydroxycarboxylic acid, which is a polyester of hydroxycarboxylic acid containing a hydrocarbon chain having 4 to 30 carbon atoms.

For example, a type of hydroxycarboxylic acid selected from lysyllic acid, 12-hydroxystearic acid, castor oil fatty acid, hydrogenated castor oil fatty acid, δ-hydroxyvaleric acid, (-hydroxycaproic acid, P-hydroxyethyloxybenzoic acid, etc.) Or two or more types of self-condensing polyesters.

(B) A polyester obtained by condensing a di- or polycarboxylic acid, a di- or polyalcohol, and optionally a hydroxycarboxylic acid, in which at least one terminal of the polyester is a hydroxyl group, and one equivalent of the carboxylic acid On the other hand, alcohol needs to be used in an equivalent amount of 1 to 1 or more.

The polyester contains a hydrocarbon chain unit having 4 to 30 carbon atoms.

Examples of the di-polycarboxylic acids used include:
Adabic acid, azelaic acid, sebacic acid, hexahydrophthalic acid, tetrahydrophthalic fi, 3,6-nindomethylene-tetrahydrophthalic acid, methylnadic acid, dodecenylsuccinic acid, phthalic acid, isophthalic acid,
Terephthalic acid, trimellitic acid, naphthalic acid, etc.
As the di-polyalcohol, for example, butane-1゜3
- Glycol, tetramethylene glycol, neopentyl glycol, hexamethylene glycol, octamethylene glycol, dihydroxymethylcyclodecane, dihydroxyethoxybenzene, etc., and the optionally added hydroxycarboxylic acid is the compound shown in (A) above. .

(C) This is an esterified product of the other end of the polyester alcohol component described in (A) and (B) above. Depending on whether the other end is a carboxyl group or a hydroxyl group, it is an ester of alcohol or carboxylic acid. These are aliphatic, alicyclic, aromatic alcohols or carboxylic acids having 1 to 30 carbon atoms, such as methyl, ethyl, propyl, butyl, hexyl, octyl, dodecyl, hexadecyl. , octadecyl-, cyclohexyl-, benzyl-alcohol etc., acetic acid, propionic acid, acetic acid, caproic acid, lauric acid, valmitic acid, stearic acid, oleic acid, linoleic acid, lysyllic acid,
These include behenic acid, tricyclodecanecarboxylic acid, and benzoic acid.

The phosphoric triester compound used in the present invention includes, in addition to the above-mentioned phosphoric triester compound of the polyester alcohol component, the reaction between the polyester alcohol component and the phosphorylating agent is limited to a diester or monoester, and other monoesters are used. Also included are asymmetric phosphoric acid triester compounds in which an ester or diester component is esterified using a conventionally known hydroxycarboxylic acid, an alcohol ester of a hydroxycarboxylic acid, or an alcohol.

It is synthesized according to a conventionally known method for synthesizing an asymmetric phosphoric acid triester compound.

Conventionally known alcohol components are used. For example, hydroxycarboxylic acids and alcohol esters thereof include ricinoleic acid, 12-hydroxystearic acid, γ-hydroxyacetic acid, δ-hydroxyvaleric acid, (-hydroxy It is an ester of caproic acid, P-hydroxyethyloxybenzoic vinegar, etc., and an alcohol having 1 to 30 carbon atoms, and the alcohol is an alcohol having 1 to 30 carbon atoms, such as methyl alcohol, ethyl alcohol, propyl alcohol. , butyl alcohol, hexyl alcohol, octyl alcohol, decyl alcohol, dodecyl alcohol, tridecyl alcohol, hexadecyl alcohol, octadecyl alcohol, tetracosyl alcohol, hexacosyl alcohol, cyclohexyl alcohol, benzyl alcohol, and the like.

In the phosphoric acid esterification reaction of the alcohol component mainly composed of polyester alcohol of the present invention described in section --, it is inert to these raw materials and products, and is capable of dissolving these raw materials, etc. It is also preferred to use organic solvents.

For example, aliphatic saturated hydrocarbons such as octane, petroleum ether, ligroin, and mineral spirits; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated aliphatic hydrocarbons such as trichloroethane and tetrachloroethane;
Solvents conventionally used in these reactions, such as chlorinated aromatic hydrocarbons such as O-dichlorobenzene and trichlorobenzene, are used.

Next, the pigment composition of the present invention will be explained in more detail.5 The pigments used in the present invention may include all conventionally known organic pigments, inorganic pigments, extender pigments, etc.

For example, organic pigments include phthalocyanine, azo, condensed azo, anthraquinone, perinone/perylene, indigo/thioindigo, isoindolinone, azomethine azo, dioxazine, quinacridone, aniline black, Triphenylmethane type, carbon black, etc. Inorganic pigment type includes titanium oxide type, iron oxide type, iron hydroxide type, chromium oxide type, spinel type fired pigment, lead chromate type, vermilion chromate type. , dark blue, aluminum powder, bronze powder, etc. Extender pigments include calcium carbonate, barium sulfate,
Silicon oxide type, aluminum hydroxide type, etc.

In the present invention, these pigments are used in the form of dry fine powder as well as
It is also used in the form of an aqueous filter cake or an aqueous suspension.

The phosphoric acid triester compound used in the present invention may be used alone or in accordance with each application with a conventionally known suitable organic solvent, a fixing agent resin such as a vehicle for paint, a varnish for printing ink, a vehicle for a coding agent, a thermal It is used with materials selected from plastic resins, thermosetting resins, plasticizers, crosslinking agents, catalysts, etc.

The pigment composition of the present invention is produced using various types of dispersing machines together with the pigment, a phosphoric acid triester compound as a dispersion aid, and the above-mentioned materials.

For example, a typical method is mixing, kneading, and grinding using a conventionally known dispersing machine such as a po mill, a sand mill, an attritor, a horizontal continuous media dispersing machine, a two-roll roll, a Miki roll, a pressurized Nigoo, a Pan Bali mixer, and an extruder. This is a great method.

In addition, when the pigment is obtained in the form of an aqueous filter cake or an aqueous suspension, the dispersion aid used in the present invention may be used alone, or in combination with a hydrophobic solvent or the above-mentioned fixing agent resin, etc. in a kneader or flasher. The pigment can be easily and efficiently transferred from the aqueous phase to the oil phase medium by the flushing method.

The amount of the phosphotriester compound used in the present invention is:
The amount is about 1 to 300 parts by weight, preferably about 3 to about 150 parts by weight per 100 parts by weight of pigment.

The pigment composition of the present invention can be used in paints, printing inks, etc.
In addition to being a composition used as a coloring agent for various purposes such as a colored coating agent and a resin coloring agent, it is also used as a high-pigment dispersion containing a high concentration of pigment.

Paints include all conventionally known paints that use pigments, such as automotive paints, architectural paints, wood paints, vehicle and equipment paints, household paints, plastic paints, and pre-coated metals. paint for cans, paint for ships, anti-corrosion coating #1. These include photo-curing paints, TL beam-curing paints, electrostatic powder paints, vinyl sol paints, etc.

The printing ink includes all conventionally known printing inks, such as letterpress ink, flat plate ink, intaglio gravure ink, stencil screen ink,
Newspaper ink, flexo ink, etc.

In the case of paints, printing inks, colored coatings, etc., the pigment content is approximately 0.1 to 20% by weight, whereas in the case of high pigment content dispersions, it is approximately 20 to 70% by weight, and a solvent is also used. In the case of easily dispersible pigments which have been treated and dried, they are produced and used in a range of approximately 60 to 95% by weight.

The use of these phosphoric acid triester compounds used in the present invention as a dispersion aid is carried out during pigment synthesis at a stage immediately after synthesis. After post-treatment such as filtration, drying and pulverization, it is added and used for crosstalk and dispersion.

Further, the amount to be used may be used in its entirety at the above-mentioned stage, or it is also an excellent method to add it in portions at each stage of the manufacturing process, for example, immediately after synthesis and at the time of dispersion.

As mentioned above, conventionally known materials are used in conjunction with each application, and organic solvents include aliphatic,
Alicyclic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons, esters, ketones, glycol ethers, alcohols, etc. are used, and there are no particular restrictions.

In addition, conventionally known materials are used as vehicles for manufacturing methods, varnishes for printing inks, vehicles for coating agents, etc., depending on the application. Resin, phenol-modified resin, modified alkyd resin such as styrenated flukyd, amino alkyd resin, oil-free alkyd resin, acrylic resin for baking, acrylic lacquer resin, acrylic polyol resin, polyester resin, epoxy resin, butylated melamine resin, methylated melamine resin, urea-melamine resin,
Phenol resin, rosin modified phenolic resin, rosin modified maleic acid resin, phenol modified maleic acid resin, polyurethane resin, styrene resin, styrene acrylic resin, styrene-diene copolymer, vinyl chloride copolymer.

Vinyl acetate resin, vinyl acetate copolymer, ethylene vinyl acetate resin, butyral resin, petroleum resin, rosin ester, modified resin such as maleated rosin ester, drying oil,
Boil oil etc.

Examples of the thermoplastic resin include polyvinyl chloride resin, styrene resin, acrylonitrile-styrene resin, acrylic resin, methacryl-styrene resin, and polyester resin.

tj7 As a plastic agent, phthalate ester, adipine ester, sebacate ester, polyester 11rq
! agents, epoxidized soybean oil, etc.

Further, the achievement of the present invention may not be hindered by adding and using conventionally known pigment dispersion aids, flushing aids, etc., if necessary.

Examples include higher aliphatic monoamines, higher aliphatic diamines, acetates and higher aliphatic salts thereof.

(Function/Effect) The phosphoric acid triester compound bonded with polyester chains used in the present invention is used in the field of coloring materials such as pigments, paint printing inks, and plastic colorants, although it was found in the natural phospholipid lecithin described above. It has no fear of deterioration or putrefaction due to oxidation or rancidity, has excellent stability, and has excellent effects in surface modification, dispersion in media, etc.

The phosphoric triester compound bonded with polyester chains used in the present invention is adsorbed onto the surface of pigments due to its phosphoric acid ester bonds, the charge-absorbing properties of the ester bonds, the hydrophilic properties of the hydrocarbon chains, etc. It improves the wettability to the medium, and as a dispersion aid it improves the dispersibility and fluidity in the medium.It also serves as a flushing aid from aqueous source cakes, etc. to make the surface of the pigment lipophilic and hydrophobic. It can be easily and efficiently flushed.

Next, the present invention will be specifically explained with reference to reference examples, production examples of phosphoric acid triester compounds, and examples.

Note that parts and percentages in the text are based on weight.

Reference Example 1 (1) Synthesis of self-condensing polyester of 12-hydroxystearic acid and its methyl esterification reaction.

Backflow condenser with stirrer, thermometer and moisture meter.

A four-necked glass reactor with an inlet and an oil bath were prepared.

100 parts of 12-hydroxystearic acid and 100 parts of toluene were charged therein and dissolved by stirring. After dissolving, the temperature is raised, and P-toluenesulfonic acid 1.
The temperature of the 0 reaction solution to which 0 part was added was raised to 120° C. to allow the self-condensation polyesterification reaction of 12-hydroxystearic acid to proceed.

The progress of the reaction was determined by the amount of leaked water and the infrared absorption spectrum of the reactants at 60 minutes, 120 minutes, and 180 minutes.
The polyesterification reaction was completed by cooling in 0 minutes.

Then, when the temperature reached 63°C, 50 parts of methanol, 100 parts of methyl acetate, and 0.5 parts of P-)luenesulfonic acid were added.
The temperature was raised to 110° C., and the methyl esterification reaction was proceeded while leaking the solvent. At the point where 150 parts were distilled and leaked, the temperature was lowered to 63°C, 200 parts of methanol was added, and 110 parts of methanol was added.
The temperature was raised to ℃ and the solvent was distilled off. The amount distilled off was 245 parts.

After the methyl esterification reaction took about 5 hours, 300 parts of water was added to extract the aqueous component, and the oil layer was separated into two layers. For dehydration, 150 parts of toluene and 200 parts of methanol were added to the oil layer, the temperature was raised to 130° C. while blowing nitrogen gas, and the solvent was distilled off. The leakage amount was 345 parts.

The reaction product obtained was an amber liquid, and analysis of infrared absorption spectra and gel permeation chromatography showed that it was a methyl ester of a self-condensed polyester of 12- and droxystearic acid. Confirmed with data.

Measurement of the acid value of the reaction product confirmed that the methyl esterification reaction of the polymer was almost complete. Moreover, the measured value of the hydroxyl value of the reaction product was 40.8. From this, 1 gram equivalent of the methyl ester of this self-condensed polyester of 12-hydroxystearic acid is 1.375, and the average degree of condensation polymerization from this is approximately 5.

(2) Synthesis reaction of phosphoric triester compound of methyl ester of self-condensing polyester of 12-hydroxystearic acid.

A four-necked glass reactor with stirrer, thermometer, addition funnel, backflow condenser, and water bath were prepared.

Into the reactor were 188.2 parts of methyl ester of the self-condensed polyester of 12-hydroxystearic acid obtained in (1) above (1 gram equivalent is 1, 375), and 188.2 parts of benzene.
1 part and 16.6 parts of triethylamine were mixed and dissolved.

Separately, 7.0 parts of phosphorus oxychloride was charged into a dropping funnel and charged into the reactor.

The equivalent ratio of the polyester having a hydroxyl group, phosphorus oxychloride and triethylamine is 3:3:3.6.

The reaction solution is cooled while stirring, and phosphorus oxychloride is added dropwise from the dropping funnel over 30 minutes while being careful not to allow the temperature of one reaction solution to rise above 10°C. After the addition was completed, the reaction solution was stirred for 2 hours and then cooled.

Next, in order to remove triethylamine and its hydrochloride as a decondensation catalyst from the reaction product solution, using a separating funnel,
It was washed three times with the same amount of ion-exchanged water, half of Hananoic acid acidic water, and half of ion-exchanged water.

After drying the washed benzene layer with sodium sulfate,
Benzene was distilled off under reduced pressure to obtain a brown liquid reaction product.

The reaction product was analyzed by infrared absorption spectrum and gel permeation chromatography.
- It was confirmed to be a phosphoric triester compound of methyl ester of self-condensed polyester of hydroxystearic acid.

The approximate average molecular weight of EJ&min was 4,200 (referred to as Dispersant 1).

Reference Examples 2 to 12 Various phosphate ester compounds were obtained in the same manner as in Reference Example 1 (2), using the materials listed in Table 1 below in place of the materials in Reference Example 1 (2). .

Reference Example 13 23.6 parts of phosphorus oxychloride was charged into the four-necked glass reactor equipped with the stirrer, thermometer, dropping funnel, and backflow condenser used in Reference Example 1 (2).

Separately, methyl ester of 12-hydroxystearic acid was synthesized in the same manner as in Reference Example 1 (1) (average molecular weight: 1
．． It is 440. ) 147.7 parts to 147.7 parts of benzene
1 part and 12.5 parts of triethylamine were mixed and dissolved and charged into a dropping funnel.

It was gradually added dropwise over 2 hours at 5-10°C.

The pigment was incubated at 10° C. for 1 hour.

Furthermore, methyl ester of 12-hydroxystearic acid (average molecular weight is 600) synthesized in the same manner3
0.8 part was mixed and dissolved with 30.8 parts of benzene and 6.2 parts of triethylamine, charged into a dropping funnel, and then 1
Add dropwise over 1 hour at 0-20℃, 20℃, 40℃
℃, stirred for 1 hour while gradually increasing the temperature to 60℃,
The mixture was further stirred and reacted at 80° C. for 2 hours, and then cooled.

In the above, polyester alcohol with an average molecular weight of 1,440, polyester alcohol with an average molecular weight of 600,
The equivalent ratio of phosphorus oxychloride and triethylamine is 2:
The ratio is 1:3:3.6.

A reference example of the cooled reaction product liquid! A brown liquid reaction product was obtained by washing, purifying, drying, concentrating, and removing the solvent in the same manner as in (2).

Analyzing in the same manner as in Reference Example 1 (2), it was found that it is a triester of methyl ester of poly-12-hydroxystearic acid, and the approximate average molecular jIX of its main component is approximately 3,500.
(referred to as dispersant 13).

Reference Examples 14 to 19 Various phosphoric ester compounds were obtained in the same manner as in Reference Example 13, except that the materials listed in Table 2 below were used in place of the materials in Reference Example 13.

Example 1 Aqueous filter cake of copper phthalocyanine blue pigment (C,1, Pigment Blue 15-3) (pigment content 42%) 2
38 parts were placed in a flasher, and then 20 parts of the dispersion aid 1 obtained in Reference Example 1 were added, followed by kneading and flashing according to a conventional method. The water content of the cake was released much more easily than in conventional flushing aids, and the copper phthalocyanine blue pigment was transferred to the oily phase of the dispersion aid.

Furthermore, water was completely removed to obtain a flashed color containing copper phthalocyanine blue pigment.

An offset plate printing ink for underprinting was prepared using a flashed color containing a copper 7 talocyanine blue pigment obtained in the above process.

Copper Phthalocyanine Blue Pigment 7 Rashid Color (purity 83%) 23.5 parts Mixed varnish for offset lithographic ink 72.0 parts 5% Cobalt dryer 0.2 parts 8% Manganese dryer 1.0 parts Otsudoko Above you
−−−−−−Yuyu 1 total
In the 100-part book, the blended varnish for offset lithographic ink has the following formulation.

Rosin modified phenolic resin 35 parts Oil transferability
25 parts oil transferable modified isophthalic acid alkyd 10 parts ink solvent vent
29.5 parts Aluminum chelate 0.5 total 100 parts The copper phthalocyanine blue pigment ink obtained above was printed as an indigo ink on high quality paper using an offset printing machine to obtain one bright indigo printed matter.

In addition, instead of the aqueous filter cake of copper phthalocyanine blue pigment described above, an aqueous filter cake of disazoi-nilow pigment (C, 1, pigment yellow 12) (pigment content 2
7%), Brilliant Carmiso 6B pigment (C, 1, Pigment Red 57-1) using an aqueous filter cake (pigment content 25%) to make a flushed color in the same manner as J 2 pairs. Yellow and red offset lithographic inks were prepared respectively.

In the same manner, a flashed color was obtained from an aqueous filter cake using Lake Red C pigment (C, 1, l: 'Gment Red 53-1), and a full red ink for offset lithography was obtained. Also,
A flashed color was obtained from an aqueous filter cake of copper phthalocyanine green pigment (C, 1, Pigment Green 7) to obtain a grass ink for offset lithography.

In each case, water was easily separated in flushing and showed excellent transition to the oil phase, and clear and excellent printed matter was obtained in offset plate printing.

Furthermore, dispersion aids 2 to 19 were used in place of dispersion aid 1 used above, and excellent effects similar to those described above were obtained.

Example 2 Carbon black pigment 20 parts Dispersion aid 1 obtained in Reference Example 1 6 parts Offsade ink
・Varnish 69 parts total
Carbon black pigment was mixed and dispersed using a Miki roll in a blend of 95 parts. The Car Pump Black pigment dispersed very well in the varnish.

Varnish inclusion of carbon black pigment obtained above 95 parts 5% cobalt dryer 0.2 parts 8% manganese dryer 1.0 parts
- Knee 11 total
A carbon black ink was obtained by sufficiently uniformly mixing and cross-mixing at 100 parts. This was used to print with an offset printing machine to obtain a black printed matter with a high degree of blackness. Further, in place of the dispersion aid 1 used above, dispersion aids 2 to 19 were used, and the same excellent effects as above were obtained.

In addition, the black ink obtained above was added to the yellow ink, red ink, and indigo ink obtained in the example to produce four colors as process ink, process red ink, process C ink, and process black ink for offset lithography. Process printing was performed and clear and beautiful multicolor printed matter was obtained.

Example 3 Flashed color of the copper phthalocyanine blue pigment obtained in Example 1 (purity 83%) 6.5 parts Rutile titanium white 2.0 parts Quick-drying styrenated alkyd resin 72.6 parts Kijirol 6.
6 parts mineral spirits 11.9 parts 6%
Cobalt naphthenate 0.3 parts Ichibanbo-o
, i convenience total 100
The mixture O is sufficiently uniformly dispersed according to the recipe in the section, and JaStφ
A blue quick-drying enamel that dries at room temperature for metal materials such as vehicles was obtained. When applied, the paint was clear and beautiful.

Next, in place of the copper phthalocyanine blue pigment of Example 1, disazo yellow (C,1, Pigment Yellow 14
), fast yellow pigment made by diazotizing 4-aminophthalimide and coupling with acetoacedoanilide, Watching Red (C,1, Pigment Red 48), Chikaramin FB (C,1, Pigment Red 3)
Flushing was carried out in the same manner as in Example 1 using the aqueous filter cake of each pigment to obtain flushed colors of each pigment.

These were used in place of the copper phthalocyanine pigment in the composition of the above paint, and paints of various colors were obtained, and clear and beautiful coated plates were obtained.

Example 4 10 parts dry and crushed pigment of copper phthalocyanine blue pigment (C, 1, Pigment Blue 15-3) Dispersion aid l obtained in Reference Example 1 2 parts Kijirol
Part 13! Kujinji'' 2-1---------
−−−−−Milk recruitment total
A dispersion of copper phthalocyanine blue pigment in a mixed solvent of quidylol-butanol was obtained by dispersing 30 parts using a continuous horizontal media disperser.

Next, a paint was prepared using the following recipe.

Solvent dispersion containing copper phthalocyanine blue obtained in the above and dispersant l 3 parts rutile titanium white 14 parts thermoplastic acrylic resin
70 parts triol 6.
8 parts Kijirol 3.2 parts Butanol 2.2 parts Cellosolve
0.8 total
100 parts of this was applied as an acrylic lacquer enamel for automobiles, and a clear and beautiful coating was obtained.

Also, instead of dispersant 1 used above, dispersant 2
-19 was used, and excellent coatings were obtained similar to those described above.

(Margin below) Procedure amendment stamp ship March 4, 1985

Claims (4)

[Claims] (1) A pigment composition containing a pigment and a dispersion aid, wherein the dispersion aid is a phosphoric acid ester compound represented by the following general formula. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, -X in the formula is -A-R (-A- in the formula is a self-condensed polyester of hydroxycarboxylic acid, and its terminal is a carboxyl group or alcohol. (consisting of an ester group), and -Y and -Z are -
AR, -B and -C (-B in the formula is a group of carboxylic acid or its ester, and -C is a residue of alcohol). ] (2) The phosphoric acid ester compound according to claim (1), wherein the polyester chain of hydroxycarboxylic acid is a polyester chain of hydroxycarboxylic acid containing a hydrocarbon chain having 4 to 30 carbon atoms. (3) Production of a pigment composition characterized in that the pigment is treated with a phosphoric acid ester compound represented by the following general formula by further adding an organic solvent, a fixing agent resin, a synthetic resin, and a plasticizer as necessary. Law. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, -X in the formula is -A-R (-A- in the formula is a self-condensed polyester of hydroxycarboxylic acid, and its terminal is a carboxyl group or its alcohol -Y and -Z are -A-R, -B and -C (-B in the formula is a group of carboxylic acid or its ester, - C is an alcohol residue). ] (4) The method for producing a pigment composition according to claim (3), wherein the polyester chain of hydroxycarboxylic acid is a polyester chain of hydroxycarboxylic acid containing a hydrocarbon chain having 4 to 30 carbon atoms.