JPS63260962A - Phthalocyanine derivative and pigment composition - Google Patents

Abstract

PURPOSE:To improve the light stability of a blended pigment and the light stability of materials to be colored and retaining a pigment compsn. dispersed therein, by blending a phthalocyanine derivative represented by the specific formula with other pigment. CONSTITUTION:This phthalocyanine derivative is represented by formula 1, wherein Pc is an n-valent residue of phthalocyanine; X is a methylene, carbonyl or sulfonyl group; R1 and R2 are each H, an alkyl or allyl group provided that at least one of R1 and R2 is always a group other than H; n is 1-4. Pc is pref. a residue of copper phthalocyanine. A pigment compsn. consisting of said phthalocyanine derivative of formula I and at least one org. pigment and/or at least one inorg. pigment is formed. The amount of the phthalocyanine derivative to be blended is pref. at least 0.1%.

Description

Detailed Description of the Invention (Industrial Field of Application) The present invention relates to a phthalocyanine derivative and a pigment composition,
More specifically, the present invention relates to a novel phthalocyanine derivative that can improve the photostability, such as the resistance and light resistance, of phthalocyanine pigments and other iodine pigments, and a pigment composition containing the phthalocyanine derivative.

(Prior Art) In the past, phthalocyanine pigments such as copper phthalocyanine pigments have been widely used as blue to green pigments, which are the best among punch pigments, and have also been used in pigment compositions blended with other organic pigments or inorganic pigments. It is also widely used.

These phthalocyanine pigments, like other pigments, are used as colorants for fibers, plastics, paints, printing inks, etc., so they are difficult to mix with the dispersion medium of the fibers, plastics, paints, printing inks, etc. that are the materials to be colored. Relationships are also important. In other words, no matter how good the pigments themselves are in terms of photostability, if the photostability of the material to be colored in which these pigments are dispersed and held is only a fraction of the photostability, then it is possible to take advantage of the excellent properties of those pigments. I can't.

(Problem to be solved by the invention) Although phthalocyanine pigments have the best photostability among organic pigments, their photostability is not sufficient compared to inorganic pigments, and It is desired to improve stability.

In addition, phthalocyanine pigments are often used in combination with other organic pigments, and if the other organic pigments in this case do not have sufficient photostability, the color of the colored product will change. Unable to take advantage of characteristics.

Furthermore, if the light stability of the dispersion medium, which is the material to be colored, is low, deterioration such as reduced gloss, chalking, cracking, blistering, and interlayer peeling will occur, so the characteristics of phthalocyanine pigments cannot be fully demonstrated. Not done.

Various light stabilizers have been used to solve the above problems.

These conventional light stabilizers are mainly used to prevent photodeterioration of resins such as plastics and vehicles, and therefore have a structure that absorbs the same wavelengths (particularly ultraviolet rays) that cause deterioration in these resins. Since it is a low molecular weight compound with a relatively low melting point, it has a low photostabilizing effect on pigments that mainly absorb visible light, and shows almost no effect even when used in large quantities. In addition, although it shows some effect on plastics and vehicles, if it is used in the amount of S to further improve photostability, the compatibility with plastics and vehicles is poor, so bleeding and migration may occur. Problems have arisen in that it cannot be used for many purposes because it causes problems such as the above and reduces the effects of adding other additives.

Therefore, there is a need for a colorant that has a large photostabilizing effect on both the pigment and the coloring material that is its dispersion medium, and does not cause the various problems described above.

(Means for Solving the Problems) As a result of intensive research in order to meet the demands of the prior art as described above, the present invention has been developed by introducing a specific group having a photostabilizing effect into a conventionally known phthalocyanine compound. Furthermore, by blending the phthalocyanine derivative with other organic pigments, not only the light stability of the blended pigment is improved, but also the light stability of the pigment composition is improved. The present invention was completed based on the finding that the photostability of the coloring material itself is also significantly improved.

That is, the present invention consists of two inventions, the first invention being a phthalocyanine derivative represented by the following general formula (I), and the second invention being a phthalocyanine derivative represented by the following general formula (I). A pigment composition comprising a derivative and one or more organic pigments and/or one or more inorganic pigments.

In the above formula, PC&'in represents a phthalocyanine residue, X represents a methylene group, a carbonyl group or a sulfonyl group, R1 and R2 represent a hydrogen atom, the same or different alkyl group or allyl group, and R, R2 and R2 are not hydrogen atoms at the same time. n represents an integer from 1 to 4.

(Function) By introducing a specific group having a photostabilizing effect into a phthalocyanine compound, the photostability of the phthalocyanine compound itself, other pigments blended with the phthalocyanine derivative, and materials to be colored by these can be improved. improves.

(Preferred Embodiments) Next, the present invention will be described in more detail by citing preferred embodiments of the present invention.

The phthalocyanine derivative represented by the general formula (I), which mainly characterizes the present invention, is obtained by introducing a reactive group such as a chlorosulfonyl group, a chloromethyl group, or a carbonyl group into a phthalocyanine compound, and reacting it with a 5-aminobenzotriazole compound. obtained by

The phthalocyanine compound used is 5! ! Metal phthalocyanines are representative examples of metal phthalocyanine and copper phthalocyanine, and these phthalocyanine compounds may have one or more substituents such as chlorine, bromine, methyl group, nitro group, etc. All of these phthalocyanine compounds or substituted products thereof are known, and any of the known phthalocyanine compounds can be used in the present invention. Particularly preferred phthalocyanine compounds are copper phthalocyanine and its less chlorinated products.

The introduction of chlorosulfonyl and chloromethyl groups may also be carried out by known methods; for example, chloromethyl groups can be easily introduced by heating a phthalocyanine compound in chlorosulfonic acid, and chloromethyl groups can be easily introduced by heating a phthalocyanine compound in chlorosulfonic acid. Furthermore, the carboxyl group can be easily introduced by reacting with formaldehyde, and the carboxyl group can be easily introduced by using trimellitic acid or the like instead of phthalic acid or as a part of phthalic acid when synthesizing phthalocyanine. A carboxyl group can be converted into an acid chloride by halgenating the group. All methods of introducing these groups are conventionally known, and conventionally known methods can be used as they are.

The number of these reactive groups introduced into the phthalocyanine compound is not particularly limited, but is generally 1 to 4. In addition, all phthalocyanine compounds are not introduced into the molecule,
On average, 0.01 to less than 1 per molecule may be increased to 4. In this case, it becomes a mixture of the phthalocyanine compound in which the above-mentioned reactive group has not been introduced and the phthalocyanine compound that is increased to 4, and the surface A pigment composition of the phthalocyanine derivative of general formula (I) and a phthalocyanine pigment is obtained.

The 5-aminobenzotriazole compound reacted with the above reactive group has the following general formula (n).

The above-mentioned 5-aminohenzotriazole compound is a known compound, and any known compound can be used in the present invention, but preferred examples are as follows.

(1) 2-(3″-methyl-2′-hydroxyphenyl)-5-aminobenzotriazole, (2) 2-(3
',5'-dimethyl-2'-hydroxyphenyl)-5
-aminobenzotriazole, (3) 2- (3'-t-butyl-5'-methyl-2'
-hydroxyphenyl)-5-aminohencitriazole, (4) 2-(3',5''-di-t-butyl-2
'-Hydroxyphenyl)-5-aminohencytriazole.

(5) 2- (3'', 5'-G-t-amylu2'-
hydroxyphenyl)-5-aminobenzotriazole, (6) 2-(3”, 5′-di-t-octyl-2′-hydroxyphenyl)-5-aminobenzotriazole, (7) 2-[3′,5” -di(α,α-dimethylbenzyl)-2′-hydroxyphenyl]-5-aminobenzotriazole, (8)2-[3′-(α,α-dimethylbenzyl)-
5′-methyl-2′-hydroxyphenyl]-5-aminobenzotriazole, (9) 2-[3”-(α, α
-dimethylbenzyl)-5'-t-butyl-2'-hydroxyphenyl]-5-aminobenzotriazole, (
10) 2-[3”-(α,α-dimethylhensyl)
-5'-t-octyl-2'-hydroxyphenyl]-
5-aminobenzotriazole, (11) 2-[3
"-t-butyl-5'-(α,α-dimethylpencil)
-2'-hydroxyphenyl]-5-aminobenzotriazole, (12) 2-[3'-t-octyl-
5'-(α.

α-dimethylbenzyl)-2′-hydroxyphenyl]
-5-aminobenzotriazole, (+3) 2- [
3”-(α-methylbenzyl)-5′-t-octyl-
2'-Hydroxyphenyl]-5-aminobenzotriazole, (N)2-(3'-benzyl-5'-t-butyl-2'-hydroxyphenyl)-5-aminohencytriazole, (15) 2- (3' -N-phenyl sulfamide (5"-t-butyl-2'-hydroxyphenyl)-5-
aminobenzotriazole, (+6) 2-(3'-t-butyl-5'-methoxy-2'-hydroxyphenyl)-5-aminobenzotriazole, and the like.

The reaction between the above-mentioned 5-aminobenzotriazole compound and the above-mentioned phthalocyanine derivative having a reactive group can be carried out, for example, in an inert solvent such as 0-dichlorobenzene, nitrobenzene, dimethylformamide, etc., so that the functional group ratio of the two is By reacting at a ratio of about 1:1 at a temperature of 30 to 200°C for about 30 minutes to 10 hours, the phthalocyanine derivative of the general formula (1) can be obtained. The resulting phthalocyanine derivative of general formula (I) is an insoluble solid with a dark blue to dark green appearance.For example, it dissolves in concentrated sulfuric acid or chlorosulfonic acid and precipitates in water or ice water. Or, if it is ground into a pigment form according to a conventional method, it becomes a bright blue to green solid.

The phthalocyanine derivative of general formula (I) as described above can be used as a blue to green organic pigment, but the most preferable method of use is to use it in combination with other organic pigments. This method uses it as a light stabilizer. The most preferred other organic pigments are conventionally known phthalocyanine-based blue to green pigments. The pigment composition of the present invention can be obtained by mixing these known blue to green phthalocyanine pigments and/or other organic pigments. For example, when the phthalocyanine derivative of the general formula (I) has a large number of benzotriazole substituents (for example, 3 to 4 parts), The amount used can be as small as the comparative example.
On the other hand, when the number of substituents is small (for example, 1 or 2), it is preferable to use a relatively large amount.

Any known method may be used to blend the phthalocyanine derivative of general formula CI) into the organic pigment.

For example, the following method is generally widely used.

(1) A method in which a necessary amount of the phthalocyanine derivative of general formula (I) is added at the time of pigmentation treatment of an organic pigment, for example, at the time of milling treatment, and mixing and milling treatment is carried out.

(2) The general formula (
Method I) of adding and mixing a phthalocyanine derivative.

(3) A method of adding and mixing into a pigment that has already been subjected to pigmentation treatment.

(4) A method in which a phthalocyanine derivative of general formula (I) is added and mixed together with an organic pigment during the preparation of printing inks, paints, etc.

(5) Colorants for plastics, fibers, etc., a method of adding and mixing a phthalocyanine derivative of general formula (I) to an organic pigment during J production, etc.

The pigment used in the present invention may be any conventionally known pigment. For example, organic pigments include phthalocyanine, anthraquinone, quinacridone, azo, indigo, quinophthalone, isoindolinone, Any organic pigment such as quinazoline type, dioxazine type, anthrone type, perinone type, perylene type, picoline type etc. can be used, and inorganic pigments include titanium oxide type, iron oxide type, iron hydroxide type, etc. Chromium oxide type, spinel fired pigment, lead chromate type, vermilion chromate type, navy blue type, aluminum powder, bronze powder, etc.
Extender pigments include calcium carbonate, barium sulfate,
Any inorganic pigment such as silicon oxide, aluminum hydroxide, or carbon black can be used.

Also, combinations of the above pigments (combinations include organic-batter, organic-
The pigment may be either inorganic or inorganic-inorganic, and the mixing ratio of these pigments is not particularly limited).

(Effects) According to the present invention as described above, when the phthalocyanine derivative or pigment composition of the present invention is used in applications that are directly or indirectly exposed to light, such as fibers, plastics, paints, and printing inks, the pigment Stability against light has been significantly improved, and deterioration such as discoloration and fading due to light is greatly reduced.

In particular, in mixed pigment systems consisting of two or more types of pigments (usually used as colorants in this form), the light resistance has conventionally been determined by the pigment with the least stability against light. Therefore, the balance of light resistance must be taken into account when selecting pigments, and in applications that require stability against light, it is natural that costs such as clarity and variety of hues must be sacrificed. However,
By using the pigment composition of the present invention, most of these sacrifices can be overcome.

Furthermore, the phthalocyanine derivatives used in the present invention are
Unlike conventional light stabilizers, it is in the form of a pigment, so it does not have any adverse effects such as bleeding or migration on colored materials used in various applications such as fibers, plastics, paints, and printing inks, and is not selective to colored materials. It also acts as a light stabilizer for colored materials,
Since deterioration caused by light such as yellowing, chalking, cracking, blistering, and delamination of the coloring material can be greatly improved, if the phthalocyanine derivative or pigment composition of the present invention is used, a light stabilizer can be added to the coloring material. There is no need to add.

Next, the present invention will be explained in more detail by giving Examples, Usage Examples, and Comparative Examples. In addition, unless otherwise specified, parts or percentages in the text refer to weight J! It is standard.

Example 1 57 parts of copper phthalocyanine was added with stirring while cooling to avoid the addition of vA sulfuric acid. Further, 9.5 parts of paraformaldehyde was added and the mixture was further stirred well.

Next, a catalytic amount of aluminum chloride was added, followed by 22 parts of chlorosulfonic acid, and the reaction was carried out at 20 to 25°C for 200 hours. After the reaction, the slurry was poured into ice water to precipitate the reaction product, and after filtration, it was thoroughly washed with cold water and dried at low temperature to remove the chloromethyl derivative of copper phthalocyanine.
I did sr-m.

The obtained product was dispersed in 1,200 parts of 0-dichlorobenzene, and 2-[3',5'-di(α.α-dimethylbenzyl)-2'-hydroxyphenyl]-5-amino After adding 138 parts of benzotriazole, a catalytic amount of pyridine was added and the temperature was gradually raised to 80°C. 5 at 80℃
After reacting for an hour, the temperature was further increased to 160℃, and the temperature was increased to 160℃.
The reaction was completed for 3 hours.

After the reaction, the solvent was removed by steam distillation, followed by filtration, washing and drying to obtain 165 parts of the copper phthalocyanine derivative of the present invention. In the general formula (I) of this phthalocyanine derivative, n was approximately 2.6 (a mixture where n is 2 and 3).

Example 2 57 parts of copper phthalocyanine was added to 400 parts of chlorosulfonic acid, the temperature was gradually raised to 70°C, and the reaction was carried out at 70°C for 10 hours.

The obtained slurry was cooled to 20° C. and then slowly poured into a saline solution containing lots of ice to obtain a chlorosulfonated copper phthalocyanine derivative.

This was heated to 10°C to prevent the sulfonyl chloride group from decomposing.
Filter and wash at:

Then, in 1,000 parts of N,N-dimethylformamide, 91.2 parts of 2-[3'-(α,α-dimethylbenzyl)-5'-t-octyl-2'-hydroxyphenyl-5-amino The above water paste of chlorosulfonated copper phthalocyanine was gradually added to the slurry in which benzotriazole was dispersed, and the temperature was raised to 80°C.
Perform a time line combination reaction. Thereafter, the temperature was further raised to 120°C, and the reaction was carried out at 120°C for 3 hours, after which it was cooled and the reaction solution was poured into water. This is filtered, washed and dried to obtain the copper phthalocyanine derivative of the present invention. Ta. n in the general formula (I) of this phthalocyanine derivative was approximately 1.8 (
mixture where n is 1 and 2).

Example 3 288 parts of copper phthalocyanine was added to 2.000 parts of concentrated sulfuric acid at 20° C. or lower, and 3.3 parts of rose formaldehyde were added thereto and thoroughly stirred.

Next, 7.6 parts of chlorosulfonic acid was added to
The reaction was carried out at 5°C for 15 hours. After the reaction, the slurry was poured into ice water to precipitate, and after filtration, the chloromethylated product was isolated by thoroughly washing with cold water and drying at low temperature. The number of chloromethyl groups in this chloromethylated product is about 0.2 per mole of phthalocyanine, and it is a mixture of chloromethylated copper phthalocyanine and unreacted copper phthalocyanine.

The resulting product was dispersed in 2,500 parts of 0-dichlorobenzene to give 2-[3',5'-di(α,α-dimethylbenzyl)-2'-hydroxyphenyl]-5-
Add 46 parts of aminobenzotriazole and pyridine, and gradually raise the temperature to 80°C. After the reaction was carried out at 80°C for 5 hours, the temperature was further raised to 160°C, the reaction was carried out at 160°C for 3 hours, the solvent was removed under reduced pressure, and then pigmentation was carried out using a conventional method to obtain the copper phthalocyanine pigment of the present invention. A composition was obtained.

Example 4 A copper phthalocyanine pigment composition of the present invention was obtained by mixing 5% each of the copper phthalocyanine derivatives of Examples 1 and 2 into stable copper phthalocyanine.

Usage Example 1 10 each of the pigment compositions obtained in Examples 3 and 4 and the stable copper phthalocyanine pigment used in Example 4 (Comparative Example 1)
part, alkyd resin varnish (N, V.

60%) 26.4 parts, 11 parts of melamine wood 1:-su (N
, V, 50%) and 20 parts of a thinner consisting of xylene/n-butanol = 8/2 (weight ratio) in a mayonnaise bottle, glass peas were added, and the mixture was dispersed for 90 minutes using a paint shaker. After dispersion, the mixture was further diluted with 48.3 parts of the mixed varnish of alkyd and melamine [alkyd/melamine = 773 (solid content by weight)] as described above to prepare a dark enamel.

In addition, the obtained dark enamel was pig/Ti02=1
A light-colored enamel was prepared by mixing it with autoenamel to give a ratio of /20.

Each of the dark and light colored enamels prepared in this way was mixed with thinner (xylene/n-butanol - 8/2 (weight ratio).
) to a spraying viscosity, applied onto a tin plate using an air spray gun, and baked under conditions of 120''C x 30 minutes. The prepared coated plates were exposed outdoors (Iwata City, Shizuoka Prefecture, facing south, 60° angle), and the condition of each coating film was measured. The results shown in Table 1 below were obtained.

(Left below) γ′″r 1 = -z Comparison test by outdoor exposure (melamine/alkyd baking paint) Ichino Ichigo Ichi trial 51 Deaf 1 year 1 year Dan Example 3
000 △ Example 4-1 0 0 Δ △ Example 4-2
0 0 Δ Δ Comparative example 1 0 Δ
X
0 Δ Δ It was done in three stages.

Use Example 2 The stable copper phthalocyanine pigment used in Example 3 (Comparative Example 2) and the copper phthalocyanine pigment compositions obtained in Examples 3 and 4 were each mixed with zinc stearate and pig: Zn-
A dark dry color of the present invention was prepared by mixing 5L=6:4. Also, pig this dark dry color
: A light dry color was prepared by mixing with a white dry color in a ratio of TiO□=1:10.

The obtained dark and light dry colors were placed in 0.11 dishes of dark color;
Light color 0. The mixture was mixed with polyethylene resin to give 5PIIR, formed into a pellet shape using an extruder, and then a plate was created using an injection molding machine.

The resulting plate was run through a fade meter, and the Δ
The E value was measured over time and the results shown in Table 2 below were obtained.

(Left below) 71 2 2 Light resistance test using fade meter (polyethylene) Example 3 0.87 1.06 +, 53
2.37 Example 4-1 0.7 [i 1.1
8 1.78 2.89 Example 4-2 0.85
1.21 1.84 3.06 Comparative Example 2 1
．． 21 2.17 2.93 4.28 Example 3
1.04 1.28 2.1:l 2
．． 88 Example 4-1 1.10 1.52 2.
45 3.23 Example 4-2 1.1:1. 1.5
7 2.56 3.37 Comparative example 2 1.58
2.96 3.87 5.52 Example 5 In order to investigate the effects of the copper phthalocyanine derivative of the present invention, pigment compositions A to A of the present invention having the following compositions were prepared.

3 Mixed composition of mixed pigment (I) On the top of the column A on the plate A
(:,1.PB-15+3 75C,1,
PY-17:l 10(:, 1.PW
-2110 ゛ Example 15 B (:, 1.PB-15:2
2511:, 1. PV-1910 [:, 1. PW-650 C, 1, PW-2110 Example 25 CG, 1. PB-+5:4 15 (1:, 1.
PY-8320 C, 1, PY-10910 G, [, P'1-21 50 Example 15 D (:, T, PG-730C, 1, PB-
15::l 5C,1,PY-17310 C,1,PIl-620 C,1,PW-2130 Example 15 Also, corresponding to Example 5, a comparative example containing no copper phthalocyanine 1 derivative of the present invention was prepared. Pigment compositions A' to D' were prepared with the following compositions.

γz 4 -'-,-' Blend composition of mixed pigment (n) Uniform in one section--Usage Application 1 Kagogoru 1 Science and Technology A"
C, [, pH-15::l 80C,1
,PY-17310 C,1,PW-2110 B" C,1,PB-15:2 30
C,1,PV-1910 C,1,PW-650 C,1,PW-2+ 10C"
C,1,PII-15:4 20C,1,PY-
8320 C,1,PY-10910 0,1,PW-2150 D” C,1,PG-730C,1,PR-
15:3 10 C,1,PY-17310 C,1,PW-620 C,1,PW-2130 Examples of using each pigment composition of Example 5! A melamine-alkyd resin varnish was applied as a paint according to the method described in 1999, and the coated plate was exposed outdoors to measure the condition of the paint film over time.

Judgment is made by visually observing the state of deterioration such as gloss, darkening, chalking, and fading of the hue of the paint. There are 3 levels: O: Almost no deterioration, △: Some deterioration is observed, ×: Severe deterioration. I went there.

γt 5 Z-, = Resistance test by outdoor exposure (melamine/alkyd baking paint) One trial and one dan and ox ox hirotan' U and A ○
0 0 0 △ ×A' OO△ Δ
× × B 0000 △ × B' ○ OΔ Δ × ×c
,,ooo Δ Δ × C′ OΔ Δ XXXD
000 △ △ ×D ′ OΔ
Δ XXX Example 6 The phthalocyanine derivatives of the present invention shown in Table 6 below were prepared in the same manner as in the previous example.

Chi 6-F 1% (1) C1l□ Approx. 12
C mouth (2)
C1l□ Approximately 23 Fe (3)
(:112 approx. 24 Cu (4
) Cll, about 35 Cu
(5) CH2 approx. 46 (:u (6
) Cl12 Approximately 17 Cu (
7) 502 approx. 38 Cu
(8) 502 approx. 29 Cu
(9) 502 Approximately 410 Cu
(10) S02 approx. 411 C
u (II) 502 approximately 212
Cu (12) 502 approximately 11:l
Cu (13) 502 approx. 2
+4 Cu (+4) CO approx. 3
+5 Cu (+5) GO approx. 41
6 Cu (16) Go about 2 Using the phthalocyanine derivatives of the present invention No. 1 to 16 above, a pigment composition of the present invention was prepared in the same manner as in Example 4, and the pigment composition was prepared in the same manner as in Use Example 1. The effects were determined and the results shown in Table 7 below were obtained.

(Left below) γ7 7; Resistance test by outdoor exposure (melamine/alkyd baking paint) 1st base 1st base 1st base 11th test - L year Subox 14th No.
I ○ ○ O△No, 2
0 0 0 △No, :l ○
o O△No, 4 0 0
0 △N0.5 0 0 0
△No, 6 0 0 0 ΔN
o , 7 0 0 0 ΔN
o , 8 0 0 0 △N
o, 9 0 0 0 △No, +0
0 0 0 No, II OO
OΔ No, I2 0 0 0 △No
, 13 0 0 0 ΔNo, 1
4 0 0 0 ΔNo, +5
0 0 0 △No, 16
0 0 0 △-Tanichiichiri- One meter and -1 year 1 year 1 year 1 NO, l OOOΔ No, 2 0 0 0
ΔNo, :l ○ OOΔN
o, 4 0 00 △No,
5 0 0 0 △
No, 6 0 0 0 △
No, 7 0 0 0
△N o , 8 0 0
0 ΔNo, 9 0 0
0 △No, lOOOO△ No, lI O○ ○ △N
o, I2 0 0 0 ΔN
o,]3 0 0 0
△No tears ○ ○ O△

Claims (7)

[Claims] (1) A phthalocyanine derivative represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the above formula, Pc represents an n-valent phthalocyanine residue, X represents a methylene group, carbonyl group, or sulfonyl group, and R_1 and R_2 are hydrogen atoms, the same or represents a different alkyl group or allyl group, and R_1 and R_2 are not hydrogen atoms at the same time. n represents an integer from 1 to 4.) (2) The phthalocyanine derivative according to claim (1), which is a mixture of derivatives having different values of n. (3) The phthalocyanine derivative according to claim (1), wherein Pc is a copper phthalocyanine residue. (4) A pigment composition comprising a phthalocyanine derivative represented by the following general formula (I) and one or more organic pigments and/or one or more inorganic pigments. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the above formula, Pc represents an n-valent phthalocyanine residue, X represents a methylene group, carbonyl group, or sulfonyl group, and R_1 and R_2 are hydrogen atoms, the same or represents a different alkyl group or allyl group, and R_1 and R_2 are not hydrogen atoms at the same time. n represents an integer from 1 to 4.) (5) The pigment composition according to claim (4), wherein Pc is a copper phthalocyanine residue. (6) The pigment composition according to claim (4), wherein the one or more organic pigments include at least a copper phthalocyanine pigment. (7) The pigment composition according to claim (4), which contains 0.1% or more of a phthalocyanine derivative represented by general formula (I).