JPS61246261A - Pigment dispersant - Google Patents

Abstract

NEW MATERIAL:Pigment dispersants of formula I, wherein Q is a residue of an org. dye ; X is -CONH-Y2-, -SO2NH-Y2-, -CH2NHCOCH2NH-Y2- ; Y2 is alkylene, arylene ; Y1 is -NH-, -O- ; Z is hydroxyl, alkoxy, etc. ; R1 and R2 are each alkyl or they may form a nitrogen-contg. heterocyclic ring when combined together ; m is 1-6 ; n is 1-4. USE:Pigment dispersants having an excellent effect of improving non- agglomeration and non-crystallizability of org. and inorg. pigments and suitable for use as materials for the production of offset ink, gravure ink, etc. PREPARATION:An org. dye such as anthraquinone dye, azo dye, phthalocyanine dye, quinacridone dye or dioxazine dye is chlorosulfonated or chloro acetamidomethylated and reacted with an amine of formula II (e.g. a compd. of formula III) to obtain the pigment dispersant of formula I (e.g. a compd. of formula IV wherein Cu-Pc is copper phthalocyanine).

Description

DETAILED DESCRIPTION OF THE INVENTION [Object of the Invention] (Industrial Application Field) The present invention relates to a pigment dispersant that is easy to use, particularly excellent in non-aggregation and non-crystallinity.

(Prior Art) Practically useful pigments that exhibit clear color tones and high tinting power in various coating compositions generally consist of fine particles. However, the fine particles of pigments make it difficult to obtain stable dispersions when dispersed in non-aqueous vehicles such as offset inks, gravure inks and paints, which has an important impact on manufacturing operations and the value of the resulting products. It is known to cause various problems.

For example, dispersions containing pigments consisting of fine particles often exhibit high viscosities that make it difficult to remove the product from the disperser.

Not only is transportation difficult, but in worse cases, gelation may occur during storage, making it difficult to use. In addition, when different types of pigments are mixed and used, phenomena such as color separation due to aggregation and sedimentation may result in color unevenness and a significant decrease in coloring power in the developed product. Furthermore, the surface of the paint film of the developed product may suffer from poor conditions such as reduced gloss and poor leveling.

Further, although not directly related to pigment dispersion, some organic pigments experience a phenomenon that involves a change in the crystalline state of the pigment.

In other words, in non-aqueous vehicles such as offset inks, gravure inks, and paints, pigment crystal particles, which are energetically unstable, change their size and shape and shift to a stable state, resulting in a significant change in hue in the color spread9. Product value may be impaired due to a decrease in coloring power, generation of coarse particles, etc.

Many proposals have been made so far, mainly copper phthalocyanine and quinacridone pigments, for the purpose of improving the non-aggregation properties and crystal stability of pigments.

The content can be broadly divided into the following two categories based on technical methods.

Act 1 is USP 3370971 and USP 29655
As shown in No. 11, the surface of pigment particles is coated with a colorless compound such as silicon oxide, aluminum oxide, and tertiary butylbenzoic acid.

The second law is Special Publication No. 41-2466 and USP 28554.
As represented by 03, the base skeleton is an organic pigment, and the side chain has a sulfone group, a sulfonamide group, an aminomethyl group,
This is a method of mixing compounds obtained by introducing a substituent such as a phthalimidomethyl group.

Compared to the first method, the second method has a significantly greater effect on pigment disaggregation, crystal stability, etc. in a non-aqueous vehicle, and is also very advantageous judging from the ease of manufacturing the pigment composition. It's a method.

(Problems to be Solved by the Invention) The present invention provides a practically excellent pigment dispersant for solving various problems occurring in non-aqueous vehicles of offset inks, gravure inks, and paints.

[Structure of the invention]

(Means for Solving the Problem) As a result of intensive research, the present inventors have invented a practically excellent pigment dispersant.

That is, the present invention is a pigment dispersant represented by the following general formula (1).

In the formula, Q: organic dye residue.

X ;-CONH-Yz-, -S OxN H-Y2-
or -CHzN HCOCHzN H-Yz-(Y2
; an alkylene group or an ajin group which may have a substituent).

Ylow NH- or -〇-6 Z; hydroxyl group, alkoxy group or (Yshi, -NH- or -〇-) Alternatively, when n is 1, it may be -NH-X-Q.

R1+R2; Each independently substituted or unsubstituted alkyl group, or R1 and R2 together form a heterocycle containing at least a nitrogen atom.

An integer between mal and 6.

n; an integer from 1 to 4.

More specifically, 2, for example, general formulas (2), (3),
(4), (5).

It is expressed as (6) and (7).

(In the formula, *Q+ m, nt RI+ R, are the same as in general formula (1)) As the organic pigment that is a raw material for the pigment dispersant of the present invention represented by general formula (1), generally commercially available dyes or Pigments can also be used.

For example, anthraquinone dyes, azo dyes, phthalocyanine dyes, quinacridone dyes, dioxazine dyes, anthrapyrimidine dyes, anthanthrone dyes, indanthrone dyes, flavanthrone dyes, pyranthrone dyes, perinone dyes. , perylene dyes, thioindigo dyes, and other pigments or dyes.

The pigment dispersant of the present invention can be obtained by subjecting these organic pigments to chlorosulfonation, chloroacetamide methylation, and reacting them with, for example, amines represented by the following general formula (8).

Common organic solvents such as water, methanol, ethanol, acetone, dioxane, toluene, xylene, and dimethylformamide can be used in these hydrochloric acid reactions. Pyridine, triethylamine, sodium hydroxide, sodium carbonate, etc. can also be used as catalysts. In addition, when the organic dye has a substituent such as a sulfonic acid group or a carboxyl group, thionyl chloride,
After converting to acid chloride with phosphorus pentachloride etc., general formula (8)
The pigment dispersant of the present invention can be obtained by reacting with amines.

The amines represented by the general formula (8) are 9, for example, p
A compound (9) represented by the following formula is produced by reacting equimolar amounts of -amino-acedoanilide and cyanuric chloride in a common organic solvent such as alcohol, a mixed solvent of water alcohol, or quidylol.

Then, it is reacted with amines or alcohols represented by the following general formulas (10) and (11) in a common organic solvent to produce a compound represented by the general formula (12).

(In the formula, m, RI, and Rx are the same as in general formula (1))
D+ (in the formula + Y+ + Yi + m, RI +
Rz is the same as the general formula (11). Then, the amines represented by the general formula (8) can be produced by hydrolyzing the compound (12) according to a conventional method.

Note that even if one chlorine atom in general formula (9) undergoes hydrolysis to become a hydroxyl group or an alkoxy group, it can be used as a raw material for the pigment dispersant of the present invention. Also, cyanuric chloride 1
After reacting 2 moles of p-amino-acedoanilide per mole, amines serving as raw materials for the present invention can be produced in the same manner as described above.

Furthermore, by using N-acetylethylenediamine in place of p-amino-acedoanilide, amines represented by general formula (13) can be produced.

(In the formula + Y+ + Y3 + m, R1l
Rz is the same as in general formula (1)) In addition, instead of using an organic dye as a raw material, a triazine ring is first introduced into a dye/pigment intermediate, and then a pigment dispersant having an organic dye as a skeleton is finally produced. You can also.

For example, after condensing amines of general formula (12) with p-nitrobenzoyl chloride, the nitro group is reduced according to a conventional method to obtain bases of general formula (14). Azo pigment dispersants can be produced by diazotizing these bases according to conventional methods and reacting them with various coupling components.

2 (in the formula, Y++ Yy+ !Tl, R11RJ are the same as general formula (1)) Also, the amines of general formula (12) and 2
By reacting with -hydroxy-3-naphthoic acid chloride, a coupling component represented by general formula (15) can be produced. By reacting these coupling components with various diazo components, two kinds of azo pigment dispersants can be obtained.

[(In the formula, yl, y, m, R++ Rx are the general formula (
(same as 1)) Examples of the amines represented by the general formula (10) of the present invention include N,N-dimethylaminoethylamine.

N,N-diethylaminoethylamine, N,N-dibutylaminoethylamine, N,N-dimethylaminopropylamine, N,N-diethylaminopropylamine, N
, N-dibutylaminopropylamine.

N,N-dimethylaminobutylamine, N,N-diethylaminobutylamine, N,N-dipropylaminobutylamine, N,N-dibutylaminobutylamine, N,
N-diisobutylaminopentylamine, N,N-diethylaminopentylamine, N.

N-diethylaminohexylamine, N-aminomethylpiperidine, N-aminoethylpiperidine, N-aminopropylpiperidine, N-aminoethylpyrrolidine, N
-Aminopropylpyrrolidine, N-aminoethylpipericone, N-aminopropylpipericone, N-aminoethylmorpholine, N-aminopropylmorpholine, N,N
-methyl-laurylaminopropylamine, N,N-dioleylaminoethylamine, N,N-distearylaminobutylamine, and the like.

The alcohols represented by the general formula (11) include:

For example, N,N-dimethylaminomethanol, N,N
-dimethylaminoethanol, N,N-diethylaminoethanol, N,N-dibutylaminoethanol, N,
N-dibutylaminoethanol, N,N-dibutylamitubrobanol, N,N-diethylaminobutanol, N,N-dioleylbutanol.

N-hydroxymethylpiperidine, N-hydroxyethylpiperidine, N-hydroxypropylpiperidine, N
-Hydroxyethylpipecoline, N-hydroxypropylpipecoline, N-hydroxymethylpyrrolidine, N-
These include hydroxybutylpyrrolidine, N-hydroxyethylmorpholine, N-hydroxybutylbutylmorpholine, and the like. The pigment dispersant obtained in the present invention exhibits an excellent dispersion effect on all pigments that are generally commercially available. For example, azo pigments such as soluble and insoluble azo pigments and condensed azo pigments.

Phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, perylene/perinone pigments.

Organic pigments such as dioxazine pigments, vat dye pigments, and basic dye pigments, as well as carbon black, titanium oxide, yellow lead, cadmium yellow, cadmium red, Bengara,
It can be used for inorganic pigments such as iron black, zinc white, 2, navy blue, and 9 ultramarine.

The content of the pigment dispersant obtained in the present invention in the pigment is preferably 0.1 to 30 parts by weight per 100 parts by weight of the pigment. If the amount is less than 0.1 part by weight, the effect of the pigment dispersant obtained in the present invention cannot be obtained, and even if it is more than 30 parts by weight, the effect of the amount used cannot be obtained.

The method of using the pigment dispersant according to the present invention is as follows.

For example, there are the following methods.

A pigment composition obtained by premixing an IR material and a pigment dispersant is added to a non-aqueous vehicle and dispersed.

2. Add pigment and pigment dispersant separately to a non-aqueous vehicle and dissolve.

3. A pigment and a pigment dispersant are separately dispersed in advance in a nonaqueous vehicle, and the resulting dispersion is mixed.

In this case, the pigment dispersant may be dispersed using only a solvent.

4. After dispersing the pigment in a nonaqueous vehicle or the like, a pigment dispersant is added to the resulting dispersion.

There are four methods, and any of these methods can achieve the desired effect.

As for the preparation method of the pigment composition shown in 1 above, the desired effect can be obtained by simply mixing the pigment powder and the powder of the pigment dispersant related to the present invention. Either by mechanically mixing using a mill or various types of grinders, or by adding a solution containing the pigment dispersant according to the present invention to a suspension system of the pigment in water or an organic solvent, and depositing the pigment dispersant on the surface of the pigment. Even better results can be obtained if an intimate mixing method is performed, such as co-dissolving the organic pigment and pigment dispersant in a solvent with strong dissolving power, such as, and co-precipitating with a poor solvent such as water.

Further, as shown in 2 to 4 above. When using pigments and pigment dispersants, dispersion machines such as dispersion machines, high-speed mixers, homo mixers, kneaders, roll mills, Good dispersion of the pigment can be achieved by using a sand mill, attritor, etc.

Therefore, according to the present invention, offset ink vehicles such as various rosin-modified resins, gravure inks such as lime rosin varnishes, polyamide resin varnishes, or vinyl chloride resin faces, nitrocellulose lacquers, and amino alkyd resins can be air-dried or baked with paints, acrylics, etc. lacquer,
In non-aqueous vehicles such as paints and urethane resin paints, aminoacrylic resin baking exhibits good fluidity, such as lower viscosity and structural viscosity of the dispersion compared to when pigments are used alone, and at the same time, reduces color separation. Therefore, it is possible to obtain beautiful products with good gloss of printed matter or coating films without problems such as changes in crystals. In particular, conventional pigment dispersants showed a dispersing effect in oil-modified aminoalkyd resin paints, but did not show excellent dispersing effects in oil-free aminoalkyd resin paints, but the pigment dispersant of the present invention does.

Not only oil-modified amino alkyd resin paints but also oil-free alkyd resin paints have extremely excellent dispersion effects.

The pigment dispersant of the present invention is not limited to non-aqueous vehicles, and can also be used to color other printing inks, paints, and even plastics, providing a colored product with excellent dispersion effects and strong tinting power.

The outline of the method for synthesizing the pigment dispersant of the present invention will be described below as a production example.

"Parts" in the columns indicate "parts by weight."

[Production Example 1] Copper phthalocyanine Cu-PC-4SO2C,t) having the following structure obtained according to a conventional method in 300 parts of methanol, 25 parts of chlorosulfonated product of 1-3Cu-PcH copper phthalocyanine residue, and p-aminoacedoani Ride and cyanuric chloride are reacted in equimolar amounts to produce twice the molar amount of N,
After reacting N-diethylaminopropylamine, 60 parts of an amine having the following structure obtained by hydrolysis is added, and the mixture is heated under reflux for 3 hours.

After the reaction is complete, 3000 parts of water and 10 parts of sodium hydroxide are added, followed by filtration, washing with water, and drying to obtain 50 parts of a pigment dispersant (al) having the following structure.

[Production Example 2] In place of 25 parts of copper phthalocyanine chlorosulfonate in Production Example 1, 18 parts of quinacridone chloroacetamide methylated product having the following structure obtained by a conventional method was used, and the reaction was carried out in the same manner as in Production Example 1. 45 parts of pigment dispersant (b) mainly having the following structure are obtained.

[Production Example 3] After the amine of Production Example 1 and P-nitrobenzoyl chloride are condensed according to a conventional method, the nitro group is reduced to an amino group to produce a base having the following structure.

By diazotizing 56 parts of the above base according to a conventional method and reacting it with a camping component having a 9-order structure, 80 parts of a pigment dispersant (C) mainly having the following structure is obtained.

(Production Example 4) The amine of Production Example 1 and 2-hydroxy-3-naphthoic acid chloride are condensed according to a conventional method to produce a coupling component having a primary structure.

Next, 14 parts of p-nitroaniline was diazotized according to a conventional method and reacted with 63 parts of the above coupling component to obtain a pigment dispersant (d) 76 mainly having the following structure.
part is obtained.

[Production Example 5] 8.2 parts of acid chloride having the following structure obtained by chlorinating tetracarboxy copper phthalocyanine in 800 parts of dimethylformamide according to a conventional method Cu-Pc-4CO
C) 10CuPc; Copper phthalocyanine residue, N-acetylethylenediamine and cyanuric chloride are reacted in equimolar amounts, and N,N-diethylaminoethanol and N,N-dibutylaminopropylamine are reacted and hydrolyzed. Adding 180 parts of the obtained amine having the structure below,
Heat and stir at 90-100°C for 3 hours.

After the reaction is complete, 3,000 parts of water and 20 parts of sodium hydroxide are added, followed by filtration, washing with water, and drying to obtain 180 parts of a pigment dispersant (4) having the following structure.

[Production Example 6] 15 parts of perylenetetracarboxylic acid chloride having the following structure was used in place of 25 parts of the copper phtacecyanine chlorosulfonate of Production Example 1, and the reaction was carried out in the same manner as in Production Example 1 to produce mainly the following structure. 62 parts of pigment dispersant (f) having the following are obtained.

<4) [Production Example 7] 300 parts of dioxane, 12 parts of anthanthrone chloroacetamide methylated product having the following structure and 3-methyl-
4-aminoacedoanilide was reacted with 172 times the mole of cyanuric chloride, and 40 parts of an amine having the following structure obtained by reacting and hydrolyzing N-aminopropylpipecoline was added, and the mixture was heated at 90 to 100°C. Heat and stir for 2 hours.

After the reaction is complete, 1000 parts of water and 10 parts of sodium hydroxide are added, followed by filtration, washing with water, and drying to obtain 27 parts of a pigment component (g) having the following structure.

CI++ Examples and comparative examples will be described below.

In addition, the chemical structure of each pigment dispersant indicated by alphabets corresponds to that shown in the production example.

Example 1 C, 1, Pigment on vinyl chloride varnish for gravure
Yellowos 83 was blended so that the pigment content was 10% and dispersed using a sand mill to obtain a pigment dispersion. (
Comparative example) Powder of the pigment dispersant (c) was blended into the obtained pigment dispersion so that the internal grinding amount was 10% by weight based on C, 1, Pigment Yellow 83, and the mixture was uniformly stirred with a disilver to form a gravure ink. was prepared, its viscosity was measured, and compared with the viscosity of the pigment dispersion (comparative example).

The results are shown in Table 1, and the material according to the present invention has excellent fluidity. Further, the printed matter printed with this gravure ink showed excellent effects regarding color clarity, coloring strength, and gloss. In addition, a dispersion obtained by dispersing the pigment dispersant (C) in a vinyl chloride varnish for gravure using a sand mill was prepared so that the weight ratio of C,1,Ptgment Yellow 83 and the pigment dispersant (C) was 9=1. The same effect was obtained even when added to

Comparative Examples and Examples 2 to 10 Gravure Ink Test Various pigments alone (comparative examples) or various pigments were dispersed in vinyl chloride varnish for gravure so that the pigment content was 10% (25% in the case of inorganic pigments). Later, gravure inks were prepared by adding the various pigment dispersants shown in Production Examples 1 to 7, and the viscosity thereof was examined. The results are shown in Table 1, and the ink according to the present invention has excellent fluidity.

Furthermore, excellent results were obtained in terms of color clarity, coloring strength, and gloss of printed matter printed with the gravure ink.

1”c 90:10
1430 1150 720 5902 〃
g 95: 5 1550 1240 790 5
70 Comparative Example C, 1, Pig Red 17 - -
53802790 1800 9803 〃
b 90:10 2900 1410 840 6
304 〃d 95: 5 2610 1
430 760 550 Comparative example C, 1, Pig Re
d 48 - 6200 3100 1
720 12405 b 90:10
3250 1670 930 8906 〃
d 95: 5 2960 1720 840
620 Comparative Example C, 1, PigYellow34” --
8706205605207"c
95: 5 650 440 360 300B
〃f 90:10 6B0 500
420 330 palanquin C, 1, Pig shi Jhite6
' -7906005504909〃a 95
: 5 620 440 380 3405% (weight) Example 11 C and I were baked on amino alkyd resin varnish for paint.

Pigment Blue-15 with a pigment content of 6 parts by weight
A pigment dispersion was obtained by blending and dispersing in a ball mill (comparative example). Further, the pigment dispersant (a) was dispersed in xylene using an attritor to prepare a concentrated xylene dispersion of the pigment dispersant (a).

Next, the above pigment dispersion and the xylene dispersion of pigment dispersant (a) were uniformly mixed in a dissilver so that the weight ratio of C, 1, Pigment Blue-15 and pigment dispersant (a) was 9:1. A paint was prepared, the viscosity was measured, and the viscosity was compared with the above pigment dispersion (comparative example). The results are shown in Table 2, and the two products according to the present invention have excellent fluidity.

The same effect can also be obtained by adding powder of pigment dispersant (a) to the above pigment dispersion in an amount of 10 M% on the inner side relative to the pigment and uniformly mixing with a disilver.

Examples 12 to 24 Baking was performed using an amino alkyd resin varnish for paint with a pigment content of 6
% (25% for inorganic pigments) after dispersing various pigments alone (comparative examples) or dispersing various pigments, and then adding each pigment dispersant shown in Production Examples 1 to 7 to prepare a paint. , and its viscosity was measured. The results are shown in Table 2.

The amino alkyd paints used in the examples are as follows.

It had excellent fluidity and crystal stability, and also had excellent color beauty in the coating film, high tinting power, and gloss.

Furthermore, the storage stability was also excellent with little change in viscosity.

Table 2 Amino alkyd baking is the viscosity of the paint□J pigment□
Viscosity code 6123060 ) J□J C, 1, Pig Blue 15 87
0061003550261011 〃a 90:1
0266019401210106012 〃e 9
5: 526201B20119098011J@ll
C,1,PigViolet19--8100460
02210123013 〃b 90:104770
3250181099014 If 95: 539
1021601200970□IC,1,PigY
ellotm108--89006300380027
0015 〃c 90:1033602400181
099016 〃c 95: 5391021001
230970 Comparative Example C, 1, Pig Red 168
2200 1800 1610 1
51017 〃b 90:10 1090
920 940 61018 〃g 9
0:10 1120 940 760 590 Comparative example
C,1,PigRed177-3540
1620 980? 2019 〃b
90:10 1560 1070 810 6202
0 If 95: 5 1460 109
0 720 420 Comparative Example C, 1, Pig Red 1
78 810045002100 12
5021 If 95: 5 3910
2400 1230 98022 〃g
95: 5 3610 2410 990 870 Comparative Example C, 1, Pig Orange 36
700 Boo 520 48023
” c 90:10 470 360
290 270 Regarding dispersion stability, color separation stability, which is a particular problem in application, will be explained using Examples.

The paints shown in the examples in Table 2 are canted with a titanium oxide base paint prepared in advance with amino alkyd varnish so that the ratio of pigment to titanium oxide is 1710 to obtain a light-colored paint.

The light colored paint was further diluted with xylene and used for Ford Cuff 4.
Table 3 shows the results of preparing the sample for 20 seconds (25°C) and injecting it into a test tube, and observing changes in the glass wall surface.

Nonmiyo I C, 1, Pignt Blue 15 -
- Δ × ×11
a 90:10 ◎ ◎ ◎Old Tae IC, 1
, Pigment Violet 19 - -
Δ × ×13 b 90
:10 ◎ ◎ ◎JJJI#J C, 1, P
igment Red 168 − − 〇 △
△17 b 9o:to
◎ ◎ ◎kk1ml C, I, Pigmen
t Red 17B --8 × ×21
〃f95:5 ◎ ◎ ◎ Judgment ◎ Completely uniform 〇 Slight white streaks are observed Δ White striped pattern × White is completely separated In both cases, the products according to the present invention show excellent results.

Example 25 C,1,Ptgment on nitrocellulose rough car
Blend Blue 15 so that the pigment content is 6% by weight 3
It was kneaded using this roll to obtain a pigment dispersion (comparative example).

In addition, when preparing a pigment dispersion in the same manner as above, immediately before finishing kneading with three rolls, C, 1, Pigment Bl
5% by weight of pigment dispersant (e) based on ue -15
The pigment was added and mixed uniformly to prepare a paint, and the viscosity was measured and compared with the pigment dispersion described above. The results are shown in Table 4, and the one according to the present invention has excellent fluidity.

Similar results were obtained even when the dispersing machine used for preparing the above paint was changed from a three-roll dispersion machine to a sand mill.

Examples 26-34 C, 1, Pigment Blue-15 alone (
Comparative example) or C, 1, Ptgment B
Table 4 shows the viscosities of paints prepared by dispersing lue-1 and then adding the dispersants shown in the production examples so that the pigment content was 5.5%. Similarly, Table 4 shows test results regarding the viscosity of nitrocellulose lacquers using combinations of other pigments and various dispersants according to the present invention.

In all cases, the composition according to the present invention had excellent fluidity and exhibited excellent results in terms of gloss, sharpness of color tone, and tinting power in the developed coating film.

As is clear from the results in Table 5, all the products according to the present invention exhibit excellent storage stability.

Table 4 Viscosity Curr 1 of Nitrocellulose Lacquer Pigment □ Viscosity (cps) Symbol 6123060 Nanatsuki J C, 1, Pig Blue 15 - -
780045003120288025 〃e
95: 5399028002100192026
” a 90:1041302920
21201830kkMifil C,1,PigRe
d123-890060105430496
027 #d 95: 5412032301
450128028 f 85:15401
0sawa 016 (fund) 1070kkMg'll C, 1, P
igYellow12 - - 12300 B20
05320423029 〃c 90:105
43042103430292030 〃g
90:106330490030202760111@
JC, 1, Pig Orange 36 - -2
3■20101800165031”
c 90:101240 930 690 620
32〃d95: 51290 990 7
40 690 Agricultural sweet C, 1, PigB1ack6 -
13400110006280499033
〃a95: 5694056204730398
034 〃b 90:10721064105
Table 5 shows the results of storing 4403910 and measuring the subsequent viscosity.

Table 5 Nitrocellulose lacquer immediately after preparation and 3
CBM type viscosity needle) 11□l C, 1, P
tg Blue 15 - - Immediately after 7800450
03120288025 -
-3 months later 12300 7560 5230 32
10ej15:5 shift & 39902B002100
1920I 〃 3 months later 4220 2950
2130 1970 Hiso IC, 1, Pig Red
123 - - Direct & 8900601054
30496027 - -
3 months later 13000 6200 6300 5210d
Immediately after 95:5 4120323014501280I
〃 3 months later 4330 2590 1680
1320 powder JC, 1, PigOrange36-
- Immediately after 230020101800165031
- -3 months later 9300 7
600 6200 5310c 90:1G direct f&
1240930690620 # # After 3 months 1310 980 720 690 Example 35 Amino acrylic baking paint Amino acrylic baking paint is made by dispersing C, 1, Pigment Orange 36 alone (comparative example) in the paint varnish so that the pigment content is 6%, or C ,1,Ptg+nen
After dispersing Orange 36, add a pigment dispersant (
When C) was added to C,1, Ptgment Orange 36 at a ratio of 10/90 and the fluidity of the paints was compared, the paint according to the present invention showed significantly superior results.

Furthermore, when the above-prepared paint was cut using an aluminum paint base pre-prepared with aminoacrylic paint varnish so that the ratio of pigment to aluminum was 115, the paint according to the present invention exhibited extremely clear color tone and excellent gloss. Ta.

Example 36 Urethane paint varnish Urethane paint varnish contains C, so that the pigment content is 10%.
1, Pig+++ent Yellow 95 alone (comparative example) was dispersed.

Or C, 1, Pigment Yellow 95
After dispersing the pigment dispersant (C), C,1,Pigm
Comparing the fluidity and state of the developed paint film of paints added at a ratio of 10/90 to Yellow 95, 9 the paint according to the present invention had excellent fluidity and was excellent in the gloss of the developed paint film. was.

Example 37 Rosin-modified phenolic resin offset ink C, 1, Pigment Red was added to the rosin-modified phenolic resin offset ink so that the pigment content was 30%.
53 alone (comparative example) or dispersed or C,1,Pigm
After dispersing ent Red 57, add pigment dispersant (d)
C, 1, Pig+went Red 53 to 1
Offcent inks were prepared by adding the above inks in a ratio of 5/85, and their fluidity was compared using a parallel plate viscometer, and it was found that the inventive product showed significantly superior results.

(Effects of the Invention) According to the present invention, it is possible to obtain offset inks, gravure inks, and paints that have excellent dispersion stability. Color unevenness and significant deterioration in coloring power of the colored spread product can be prevented, and a colored spread product with excellent gloss can be obtained.

Claims (1)

[Claims] 1. A pigment dispersant represented by the following general formula (1). ▲There are mathematical formulas, chemical formulas, tables, etc.▼(1) Q in the formula: organic dye residue. X;-CONH-Y_2-, -SO_2NH-Y_2-
or -CH_2NHCOCH_2NH-Y_2-(Y
_2; alkylene group or arylene group which may have a substituent). Y_1; -NH- or -O-. Z: Hydroxyl group, alkoxy group, or ▲Mathematical formula, chemical formula, table, etc.▼ (Y_3; -NH- or -O-) Or, if n is 1, -NH-X-Q may be used. R_1, R_2; each independently a substituted or unsubstituted alkyl group, or R_1 and R_2 form a heterocycle containing at least a nitrogen atom. m; an integer from 1 to 6. n; an integer from 1 to 4. 2. The organic dye represented by Q in the general formula (1) is anthraquinone dye, azo dye, phthalocyanine dye, quinacridone dye, dioxazine dye, anthrapyrimidine dye, anthanthrone dye, or indanthrone dye. , flavanthrone pigments, pyranthrone pigments,
The pigment dispersant according to claim 1, which is selected from perinone dyes, perylene dyes, and thioindigo dyes.