KR20050057703A - Self-dispersible metal complex colorant coordinated with antibacterial moiety and liquid composition comprising the same - Google Patents

Abstract

The present invention relates to a metal complex colorant capable of self-dispersion and containing an antimicrobial function and a liquid composition comprising the same. The colorant is obtained by binding a ligand including a self-dispersing moiety and a ligand including an antimicrobial substance to the colorant through a coordination bond with a metal, and the liquid composition prepared by using the same does not need to add a separate dispersant. Excellent dispersibility, long-term storage stability of the liquid is excellent, and also can minimize the side effects caused by the antibacterial agent added separately, and the fastness of light resistance, water resistance and the like by the metal complex.

Description

Self-dispersible metal complex colorant coordinated with antibacterial moiety and liquid composition comprising the same}

The present invention relates to a metal complex colorant and a liquid composition comprising the same. More specifically, a ligand comprising a self-dispersing moiety and a ligand comprising an antimicrobial substance are co-dispersed with the metal complex colorant to self-disperse in the colorant molecule itself. It relates to a metal complex colorant imparted simultaneously with the antibacterial properties and a liquid composition comprising the same.

The inkjet recording method is one of non-impact printing methods, and has an advantage of less noise than contact printing methods and relatively easy color implementation compared to laser beam printers.

The non-contact printing method is further divided into a continuous ink jet method and a drop-on-demand (DOD) method. Here, the continuous inkjet method is a method of printing by adjusting the direction of the ink by changing the electromagnetic field while continuously ejecting the ink, while the DOD method is a method of spraying the ink by dropping the fine droplets, heat-bubble type It is divided into an ink jet (thermal-bubble ink jet) method and a piezoelectric ink jet (piezoelectric ink jet) method. The former ejects ink using the pressure generated from the expansion of the bubble generated by heating the ink, while the latter ejects the ink by using the pressure generated by the piezoelectric plate which is mechanically deformed by electricity.

In recent years, the dot size of an inkjet printer tends to be small, and high resolution and high quality printed matters are required. Therefore, in order to obtain a smaller dot size, the head of the inkjet printer has a smaller nozzle opening, which is likely to be clogged, and performance is influenced by deposits and the like that affect the size of the inkjet droplet. It is known that the components of the ink formulations affect the clogging of the nozzles, and in order to prevent this, wetting agents are usually added to the inkjet ink.

In particular, in the case of a water-soluble ink, a paper coating liquid or a water-soluble dispersion composition, the formation of bacteria, etc., reduces the intrinsic properties of the composition and causes problems such as stability during long-term storage. To add a separate antibacterial agent. Antibacterial agents that have been used in conventional aqueous solutions as a relatively wide range of bactericides and preservatives are 1,2-benzisothiazolin-3-one (BIT), methyl 2-benzimidazolecarbamate (methyl) 2-benzimi dazolecarbamate: Carbendazim) and the like, and added directly to the aqueous product such as ink, coating liquid or dispersion in an amount of 0.05 to 0.5% by weight to give antimicrobial and antiseptic effect to enable long-term storage.

However, while these antimicrobial agents have the advantage of having high sterilizing power and thermal stability, when used in aqueous solution products, entanglement occurs, which causes problems in securing homogeneity of the aqueous solution products, and causes skin irritation upon contact with the body. Note that there is a disadvantage that the handling is not easy. In particular, when used in the ink composition, nozzle clogging due to ink entanglement is remarkably increased, and homogeneity is also difficult to secure. In addition, in the case of using an antimicrobial agent that can suppress such side effects, there is a problem in that it is difficult to implement the optimal color because the antimicrobial properties are weak and the storage stability is deteriorated for a long time or the selection of dyes or pigments excellent in compatibility with the antimicrobial agent is difficult.

Therefore, the technical problem to be achieved by the present invention is excellent in the self-dispersibility without the addition of a separate dispersant, excellent long-term storage stability of the liquid, and also can minimize the side effects caused by the antimicrobial agent, fastness of light resistance, water resistance, etc. Is to provide an improved metal complex colorant and a liquid composition comprising the metal complex colorant.

In order to achieve the above technical problem the present invention in one embodiment,

Provided is a metal complex colorant represented by the following Chemical Formula 1, characterized in that a ligand comprising a self-dispersing moiety and a ligand comprising an antimicrobial substance are obtained by binding to a colorant through coordination bonds with a metal.

In the above formula, C is a colorant; Me is a metal; L is a ligand comprising a self-dispersing moiety; Y is a metallizable functional group selected from the group consisting of OH, NH ₂ , and COOH; A is a ligand comprising an antimicrobial substance; m and n are 1-2, respectively, provided that m + n is 3 or less.

In addition, the present invention in another embodiment,

A liquid composition is provided comprising a metal complex colorant and a liquid medium according to the invention.

In addition, the present invention in another embodiment,

There is provided a liquid composition comprising a liquid medium and a colorant mixture consisting of a metal complex colorant and a conventional colorant according to the invention.

Hereinafter, the present invention will be described in more detail.

The self-dispersing antimicrobial metal complex colorant according to the present invention is self-dispersible and antimicrobial to the colorant molecule by simultaneously binding a ligand comprising a self-dispersing moiety and a ligand comprising an antimicrobial substance to the colorant through a coordination bond with a metal. Will be granted. That is, the self-dispersing antimicrobial metal complex colorant of the present invention has excellent self-dispersibility and antimicrobial properties, so that ink can be secured for long-term storage stability without dispersing agent and antimicrobial reinforcement agent, and the metal is coordinated and combined. Color fastness such as water resistance can be improved.

The colorant according to the present invention is a metal complex colorant represented by the following Chemical Formula 1, characterized in that a ligand comprising a self-dispersing moiety and a ligand comprising an antimicrobial substance are obtained by binding to a colorant through a coordinating bond with a metal.

[Formula 1]

In the above formula, C is a colorant; Me is a metal; L is a ligand comprising a self-dispersing moiety; Y is a metallizable functional group selected from the group consisting of OH, NH ₂ , and COOH; A is a ligand comprising an antimicrobial substance; m and n are 1-2, respectively, provided that m + n is 3 or less.

As a colorant that binds to a ligand including a self-dispersing moiety and a ligand including an antimicrobial substance through a coordination bond with the metal, any colorant capable of binding to the ligands among conventionally used colorants may be used. It is preferred that it is a colorant comprising at least one metalizable azo group.

Preferably, the colorant is capable of coordinating with the metal (Me), and includes one or more metallizable azo groups represented by the following Chemical Formula 2,

In the above formula, X ₁ and X ₂ are each a metallizable functional group selected from the group consisting of OH, NH ₂ , COOH, and alkoxy having 1 to 2 carbon atoms.

Preferably, the metal (Me) is a polyvalent transition metal selected from the group consisting of Ni, Cu, Zn, Fe, Cr, Pd, Pt and Co.

Preferably, the ligand (L) comprising the self-dispersing moiety is a neutral ligand selected from the group consisting of water, ammonia, pyridine, bipyridine, terpyridine and morpholine; Or an anionic ligand selected from the group consisting of acetate, iminodiacetate and glycine, but is not limited thereto.

Preferably, the ligand (A) containing the antimicrobial substance is a compound of formula (3),

In the above formula, R ₂ is an alkylene group having 1 to 30 carbon atoms, a heteroalkylene group having 1 to 30 carbon atoms, an arylene group having 6 to 20 carbon atoms, an arylalkylene group having 6 to 20 carbon atoms, a heteroarylene group having 6 to 30 carbon atoms, or A heteroarylalkylene group having 6 to 30 carbon atoms; R ₃ is an alkylene group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an alkylthio group having 1 to 12 carbon atoms; R ₄ , R ₅ and R ₆ are each hydrogen or an alkyl group having 1 to 5 carbon atoms; K is a metallizable functional group selected from the group consisting of OH, NH ₂ and COOH.

The alkylene group in the R ₂ group used as a substituent in the compound of the present invention is a divalent compound obtained by removing two hydrogen atoms at both ends of a normal paraffinic hydrocarbon, and is preferably a straight or branched alkylene group having 1 to 30 carbon atoms. Preferably it is a C1-C12 linear or branched alkylene group, More preferably, it is a C1-C6 lower alkylene group. Further, at least one hydrogen atom of the alkylene group may be a halogen atom, a hydroxy group, a nitro group, a cyano group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, or a phosphoric acid or a salt thereof. Can be substituted.

In addition, the heteroalkylene group in the R ₂ group used as a substituent in the compound of the present invention means that the alkylene group as defined above contains a nitrogen atom, a sulfur atom, an oxygen atom or a phosphorus atom. Further, at least one hydrogen atom of the heteroalkylene group may be a halogen atom, hydroxy group, nitro group, cyano group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, or phosphoric acid or salt thereof It may be substituted by.

In addition, the arylene group in the R ₂ group used as a substituent in the compound of the present invention means a divalent compound obtained by removing two hydrogen atoms from an aromatic hydrocarbon having 6 to 20 carbon atoms containing at least one ring. The arylene group may have 1 to 3 substituents selected from the group consisting of hydroxy, halo, haloalkyl, nitro, cyano, alkoxy and lower alkylamino.

The heteroarylene group in the R ₂ group used as a substituent in the compound of the present invention means that the arylene group as defined above contains a nitrogen atom, a sulfur atom, an oxygen atom or a phosphorus atom.

The invention also provides a liquid composition comprising 1 to 20 parts by weight of the metal complex colorant according to the invention and 80 to 99 parts by weight of the liquid medium based on 100 parts by weight of the liquid composition.

In the liquid composition according to one embodiment of the present invention, the metal complex colorant is dissolved or dispersed in a liquid medium, and preferably, the liquid medium is water, at least one organic solvent, or water and at least one organic. It is a mixture of solvents, and the content of the organic solvent in the liquid medium is preferably 5 to 50 parts by weight based on 100 parts by weight of the liquid medium.

The amount of water and organic solvent added to the liquid medium can vary depending on the properties of the liquid composition, such as, for example, viscosity, surface tension, drying rate, etc., which properties also depend on the printing method in which the liquid composition is used, It may also vary depending on the type of substrate on which the liquid composition is to be printed.

Examples of organic solvents that can be used in the liquid composition according to the present invention include methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, sec-butyl alcohol, t-butyl alcohol or isobutyl alcohol. Alcohol compounds; Ketone compounds of acetone, methyl ethyl ketone, diethyl ketone or diacetone alcohol; Ester compounds of methyl acetate, ethyl acetate or ethyl lactate; Ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, butylene glycol, 1,4-butanediol, 1,2,4-butanetriol, 1,5-pentanediol, 1,2,6-hexanetriol Polyhydric alcohol compounds of hexylene glycol, glycerol, glycerol ethoxylate or trimethylolpropane ethoxylate; Ether compounds of ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol methyl ether, diethylene glycol ethyl ether, triethylene glycol monomethyl ether or triethylene glycol monoethyl ether; Nitrogen-containing compounds of 2-pyrrolidone or N-methyl-2-pyrrolidone; And one or more organic solvents selected from the group consisting of sulfur-containing compounds of dimethyl sulfoxide, tetramethylenesulfone or thioglycol.

In addition, the liquid composition according to the present invention may optionally further include 0.5 to 40 parts by weight of one or more additives selected from the group consisting of a viscosity modifier, a surfactant, a storage stabilizer and a humectant based on 100 parts by weight of the liquid composition.

Viscosity modifiers serve to adjust the viscosity of the liquid composition so that smooth jetting can be maintained. Specific examples thereof include casein, hydroxymethyl cellulose, hydroxyethyl cellulose, carboxymethyl cellulose, and the like. The content of the viscosity modifier is preferably 0.1 to 5.0 parts by weight based on 100 parts by weight of the liquid composition.

The surfactant is to stabilize the jetting performance in the nozzle by controlling the surface tension of the liquid composition, and it is preferable to use an anionic surfactant or a nonionic surfactant. Examples of anionic surfactants include salts of alkyl carboxylic acids having 1 to 1000 carbon atoms (preferably salts of alkyl carboxylic acids having 10 to 200 carbon atoms), salts of alcohol sulfonic acid esters having 1 to 1000 carbon atoms (preferably carbon atoms). Salts of alcohol sulfonic acid esters of 10 to 200), salts of alkylsulfonic acids of 1 to 1000 carbon atoms (preferably salts of alkylsulfonic acids of 10 to 200 carbon atoms), salts of alkylbenzenesulfonic acids of 1 to 1000 carbon atoms (preferably carbon atoms) Salts of 10 to 200 alkylbenzenesulfonic acids), or mixtures thereof. Examples of nonionic surfactants include polyoxyethylene alkyl ethers (wherein alkyl is an alkyl group having 1 to 1000 carbon atoms, preferably an alkyl group having 10 to 200 carbon atoms) and polyoxyethylene alkylphenyl ether (wherein alkyl is 1 to 1 carbon atoms). 1000 alkyl groups, preferably 10 to 200 carbon atoms), polyoxyethylene secondary alcohol ethers, polyoxyethylene-oxypropylene block copolymers, polyglycerol fatty acid esters, sorbitan fatty acid esters, or mixtures thereof. The content of the surfactant is preferably 0.1 to 5 parts by weight based on 100 parts by weight of the liquid composition.

Wetting agents are preferred to prevent the liquid composition from clogging at the nozzles. Polyhydric alcohols are preferred. Specific examples of humectants include glycerin, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, hexylene glycol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 2- Butene-1,4-diol, 2-methyl-2-pentanediol and mixtures thereof. The content of the humectant is preferably 5 to 30 parts by weight based on 100 parts by weight of the liquid composition.

The present invention also provides a liquid composition comprising 2 to 20 parts by weight of the colorant mixture and 80 to 98 parts by weight of the liquid medium based on 100 parts by weight of the liquid composition.

The liquid composition comprises a colorant mixture and a liquid medium consisting of a metal complex colorant according to the invention and a conventionally used colorant, optionally further comprising an additive. In the liquid composition according to the present invention, the content ratio of each component is 2 to 20 parts by weight based on 100 parts by weight of the color composition of the colorant mixture consisting of a conventional colorant and a metal complex colorant according to the present invention. It is included as much, the content of the metal complex colorant according to the present invention in the colorant mixture is preferably 1 to 15 parts by weight based on 100 parts by weight of the liquid composition.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to the following Examples.

Synthesis Example 1

(1) 80 g of ammonia was added to 1500 ml of water, and 34 g of CuCl ₂ · 2H ₂ O was added and dissolved therein. 83 g of a colorant of the following Chemical Formula 4 was added to the solution, heated to 80 ° C., sufficiently mixed, and 140 g of ammonium chloride and 700 ml of hot water were added thereto. NaCl was added thereto to precipitate, filtered, and dried in an oven to obtain 77 g of a copper complex colorant.

(2) 50 g of the copper complex colorant obtained in (1) was dissolved in 200 ml of DMF, and 18 g of trimethylsilane compound represented by the following formula (5) was added thereto, and the mixed solution was refluxed at 100 ° C. for 6 hours or more. After removing the solvent of the reaction solution in vacuo, the remaining reactant was washed and dried to obtain 45 g of an antimicrobial copper complex colorant in which one of the ligands was substituted with a trimethylsilane compound as an antimicrobial substance.

Synthesis Example 2

(1) Into 1000 ml of water, 99 g of a colorant of the following formula (6) was heated to 90 ° C., and 25 g of CuSO ₄ · 5H ₂ O dissolved in water and 25 g of an aqueous ammonia solution (30%) were added sequentially, and then, at pH 8 for 20 hours. Mix well. 100 g of ammonium chloride was added to the reaction solution, filtered, washed, and dried in an oven to obtain 79 g of a copper complex colorant.

(2) 53 g of the copper complex colorant obtained in (1) was dissolved in 200 ml of DMF, and 15 g of trimethylsilane compound represented by the following formula (7) was added thereto, and the mixed solution was refluxed at 100 ° C. for 6 hours or more. After the solvent of the reaction solution was removed in vacuo, the remaining reactant was washed and dried to obtain 43 g of an antimicrobial copper complex colorant in which one of the ligands was substituted with a trimethylsilane compound as an antimicrobial substance.

Synthesis Example 3

(1) 72 g of a coloring agent of Formula 8 and 25 g of ammonia solution (30%) were added to 800 ml of ethylene glycol, and 25 g of Co (CH ₃ COO) ₂ .4H ₂ O was added thereto, followed by sufficient mixing at 100 ° C. 800 ml of hot water and 100 g of ammonium chloride were added to the reaction solution, followed by precipitation, filtration and washing, followed by drying in an oven to obtain 58 g of a cobalt complex colorant.

(2) 47 g of the cobalt complex colorant obtained in (1) was dissolved in 200 ml of DMF, and 30 g of trimethylsilane compound represented by the following formula (9) was added thereto, and the mixed solution was refluxed at 100 ° C. for 6 hours or more. After the solvent of the reaction solution was removed in vacuo, the remaining reactant was washed and dried to obtain 48 g of an antimicrobial cobalt complex colorant in which two of the ligands were substituted with an antimicrobial trimethylsilane compound.

Example 1

Ink composition

4 g of the antimicrobial metal complex colorant of Synthesis Example 1 (2)

77 g of water

3 g of isopropyl alcohol

10 g of ethylene glycol

Glycerin 6g

The components were mixed and stirred for at least 30 minutes in a stirrer to make a uniform state. The resultant was then passed through a 0.45 μm filter to produce the desired antimicrobial ink composition of the present invention.

Example 2

An ink composition was prepared in the same manner as in Example 1, except that the antimicrobial metal complex colorant of Synthesis Example 2 (2) was used instead of the antimicrobial metal complex colorant of Synthesis Example 1 (2).

Example 3

An ink composition was prepared in the same manner as in Example 1, except that the antimicrobial metal complex colorant of Synthesis Example 3 (2) was used instead of the antimicrobial metal complex colorant of Synthesis Example 1 (2).

Comparative Example 1

Ink in the same manner as in Example 1, except that the metal complex colorant of Synthesis Example 1 (1) was used instead of the antimicrobial metal complex colorant of Synthesis Example 1 (2) and 0.5 wt% of the antimicrobial agent (BIT) was separately added. The composition was prepared. In this case, however, the amount of water was reduced by the amount of the antimicrobial agent used.

Comparative Example 2

An ink composition was prepared in the same manner as in Comparative Example 1 except that the metal complex colorant of Synthesis Example 2 (1) was used instead of the metal complex colorant of Synthesis Example 1 (1).

Comparative Example 3

An ink composition was prepared in the same manner as in Comparative Example 1, except that the metal complex colorant of Synthesis Example 3 (1) was used instead of the antimicrobial metal complex colorant of Synthesis Example 1 (1).

Comparative Example 4

An ink composition was prepared in the same manner as in Example 1, except that the coloring agent of Formula 4 was used instead of the antimicrobial metal complex coloring agent of Synthesis Example 1 (2).

Comparative Example 5

An ink composition was prepared in the same manner as in Example 1, except that the coloring agent of Formula 6 was used instead of the antimicrobial metal complex coloring agent of Synthesis Example 1 (2).

The properties of the ink compositions prepared according to the above Examples and Comparative Examples were evaluated according to the following methods.

Experimental Example 1

Long term storage stability test

100 ml each of the ink compositions obtained in Examples 1 to 3 and Comparative Examples 1 to 5 were placed in a heat resistant glass bottle and sealed, and then stored in a 60 ° C. thermostat. After leaving it for 2 months, the presence or absence of sedimentation on the bottom was evaluated and evaluated as follows.

○: no precipitate. X: There exists a deposit.

division Example Comparative example division One 2 3 One 2 3 4 5 Storage stability O O O X X X X X

Referring to Table 1, Examples 1 to 3, which are liquid compositions obtained by using the antimicrobial metal complex colorants of the present invention, Comparative Examples 1 to 3 using conventional antimicrobial substances and Comparative Examples without using antimicrobial substances Compared with the case of 4 to 5, no precipitation formation was observed, indicating that the storage stability was excellent.

Experimental Example 2

Ames test

TA98 was added to the liquid compositions obtained in Examples 1 to 3 and Comparative Examples 1 to 3, incubated for 48 hours at 37 ° C in the dark, and the number of denatured colonies was measured.

division Example Comparative example division One 2 3 One 2 3 4 5 Storage stability 83 94 90 98 101 103 389 408

Referring to Table 2, in Examples 1 to 3, which are liquid compositions obtained using the antimicrobial metal complex colorant of the present invention, Comparative Example 1 using a conventional antimicrobial agent, as compared with Comparative Examples 4 and 5 without using an antimicrobial agent. As in the case of 3 to 3 it can be seen that the antimicrobial properties.

As described above, the self-dispersing antimicrobial metal complex colorant of the present invention is obtained by binding a self-dispersing ligand and an antimicrobial material to a colorant through coordination bond with a metal. Since the fastness, such as water resistance and the like can be improved, it can be usefully used.

Claims (16)

A metal complex colorant represented by the following Chemical Formula 1, which is obtained by binding a ligand including a self-dispersing moiety and a ligand including an antimicrobial substance to a colorant through coordination bonds with metals. [Formula 1] In the above formula, C is a colorant; Me is a metal; L is a ligand comprising a self-dispersing moiety; Y is a metallizable functional group selected from the group consisting of OH, NH ₂ , and COOH; A is a ligand comprising an antimicrobial substance; m and n are 1-2, respectively, provided that m + n is 3 or less. The metal complex colorant of claim 1, wherein the colorant is capable of coordinating with metal (Me), and includes one or more metallizable azo groups represented by the following Chemical Formula 2. [Formula 2] In the above formula, X ₁ and X ₂ are each a metallizable functional group selected from the group consisting of OH, NH ₂ , COOH, and alkoxy having 1 to 2 carbon atoms. The metal complex colorant of claim 1, wherein the metal is a polyvalent transition metal selected from the group consisting of Ni, Cu, Zn, Fe, Cr, Pd, Pt, and Co. The method of claim 1, wherein the ligand comprising the self-dispersing moiety comprises: a neutral ligand selected from the group consisting of water, ammonia, pyridine, bipyridine, terpyridine and morpholine; Or an anionic ligand selected from the group consisting of acetate, iminodiacetate and glycine. The metal complex coloring agent according to claim 1, wherein the ligand containing the antimicrobial substance is a compound of Formula 3 below: [Formula 3] In the above formula, R ₂ is an alkylene group having 1 to 30 carbon atoms, a heteroalkylene group having 1 to 30 carbon atoms, an arylene group having 6 to 20 carbon atoms, an arylalkylene group having 6 to 20 carbon atoms, a heteroarylene group having 6 to 30 carbon atoms, or A heteroarylalkylene group having 6 to 30 carbon atoms; R ₃ is an alkylene group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an alkylthio group having 1 to 12 carbon atoms; R ₄ , R ₅ and R ₆ are each hydrogen or an alkyl group having 1 to 5 carbon atoms; K is a metallizable functional group selected from the group consisting of OH, NH ₂ and COOH. A liquid composition comprising 1 to 20 parts by weight of the metal complex colorant according to any one of claims 1 to 5 and 80 to 99 parts by weight of the liquid medium based on 100 parts by weight of the liquid composition. 7. The liquid composition of claim 6, wherein the liquid medium is water, at least one organic solvent, or a mixture of water and at least one organic solvent. 8. The liquid composition according to claim 7, wherein the content of the organic solvent in the liquid medium is 5 to 50 parts by weight based on 100 parts by weight of the liquid medium. The alcohol compound according to claim 7 or 8, wherein the organic solvent is methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, sec-butyl alcohol, t-butyl alcohol or isobutyl alcohol. ; Ketone compounds of acetone, methyl ethyl ketone, diethyl ketone or diacetone alcohol; Ester compounds of methyl acetate, ethyl acetate or ethyl lactate; Ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, butylene glycol, 1,4-butanediol, 1,2,4-butanetriol, 1,5-pentanediol, 1,2,6-hexanetriol Polyhydric alcohol compounds of hexylene glycol, glycerol, glycerol ethoxylate or trimethylolpropane ethoxylate; Ether compounds of ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol methyl ether, diethylene glycol ethyl ether, triethylene glycol monomethyl ether or triethylene glycol monoethyl ether; Nitrogen-containing compounds of 2-pyrrolidone or N-methyl-2-pyrrolidone; And at least one organic solvent selected from the group consisting of sulfur-containing compounds of dimethyl sulfoxide, tetramethylene sulfone or thioglycol. The liquid according to claim 6, wherein the liquid composition further comprises 0.5 to 40 parts by weight based on 100 parts by weight of the liquid composition, at least one additive selected from the group consisting of a viscosity modifier, a surfactant, a storage stabilizer and a humectant. Composition. A liquid composition comprising 2 to 20 parts by weight of a colorant mixture and 80 to 98 parts by weight of a liquid medium based on 100 parts by weight of the liquid composition. The liquid composition according to claim 11, wherein the colorant mixture comprises 1 to 15 parts by weight of the metal complex colorant according to any one of claims 1 to 5, based on 100 parts by weight of the liquid composition. The liquid composition of claim 11, wherein the liquid medium is water, one or more organic solvents, or a mixture of water and one or more organic solvents. The liquid composition according to claim 13, wherein the content of the organic solvent in the liquid medium is 5 to 50 parts by weight based on 100 parts by weight of the liquid medium. The alcohol compound according to claim 13 or 14, wherein the organic solvent is methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, sec-butyl alcohol, t-butyl alcohol or isobutyl alcohol. ; Ketone compounds of acetone, methyl ethyl ketone, diethyl ketone or diacetone alcohol; Ester compounds of methyl acetate, ethyl acetate or ethyl lactate; Ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, butylene glycol, 1,4-butanediol, 1,2,4-butanetriol, 1,5-pentanediol, 1,2,6-hexanetriol Polyhydric alcohol compounds of hexylene glycol, glycerol, glycerol ethoxylate or trimethylolpropane ethoxylate; Ether compounds of ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol methyl ether, diethylene glycol ethyl ether, triethylene glycol monomethyl ether or triethylene glycol monoethyl ether; Nitrogen-containing compounds of 2-pyrrolidone or N-methyl-2-pyrrolidone; And at least one organic solvent selected from the group consisting of sulfur-containing compounds of dimethyl sulfoxide, tetramethylene sulfone or thioglycol. The liquid according to claim 11, wherein the liquid composition further comprises 0.5 to 40 parts by weight based on 100 parts by weight of the liquid composition, at least one additive selected from the group consisting of a viscosity modifier, a surfactant, a storage stabilizer, and a humectant. Composition.