JPH0366349B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula () [In the formula, R ₁ and R ₂ are independently a halogen atom, a cyano group or a lower alkyl group optionally substituted with a lower alkoxy group, R ₃ and R ₄ are independently a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a hydroxy group or a lower alkanoylamino group, R ₅ and R ₆ are each independently a hydrogen atom, a halogen atom, a hydroxy group,
Cyano group, nitro group, lower alkoxy group, lower alkyl group, C ₁ - C ₆ alkoxy or phenoxycarbonyl group, carbamoyl group optionally substituted with lower alkyl or phenyl, C ₁ -
C ₆ alkyl or phenylcarbonyloxy group or lower alkoxy or phenoxycarbonyloxy group, Y represents a C ₂ -C ₁₀ alkylene group. ] The present invention relates to a methine compound represented by the following, a method for producing the same, and a method for coloring an organic polymer material using the same. The purpose of the present invention is to improve molded products made of organic polymer materials such as polyester, hydrophobic fiber materials such as cellulose acetate, and thermoplastic resins such as polyethylene resin, polystyrene resin, polyvinyl chloride resin, and ABS resin. The object of the present invention is to provide a compound that is colored purple to green with vivid color and excellent fastness. A methine compound represented by the general formula () is a methine compound represented by the general formula () [In the formula, R ₁ , R ₂ , R ₃ , R ₄ and Y have the above meanings. ] Compound represented by and general formula () [In the formula, R ₅ represents the same meaning as above. ] and general formula () [In the formula, R ₆ represents the same meaning as above. ] can be obtained by condensation reaction with the compound shown in the following. The condensation reaction is carried out in any inert solvent,
This is carried out by heating to 30 to 180°C, preferably 60 to 160°C. At this time, triethylamine, piperidine, pyridine, ammonium acetate, formic acid,
Addition of acetic acid, phosphorus oxychloride, thionyl chloride, etc. accelerates the reaction. As the inert solvent, methanol, ethanol, butanol, methyl cellosolve, toluene, xylene, dimethylformamide, N-methylpyrrolidone, chlorobenzene, nitrobenzene, acetic anhydride, etc. are used. When the compounds of the invention are used as dyes, hydrophobic fibers such as synthetic and semi-synthetic fibers, such as cellulose acetate fibers, especially polyester fibers, can be dyed with dyeability, PH sensitivity (degradation resistance), sublimation resistance and lightfastness. It can be dyed or printed in vivid purple or green colors with excellent reproducibility. Also,
The dye of the present invention exhibits excellent dyeing properties for dyeing fine denier polyester fibers and artificial leather, which have been increasing in recent years. Furthermore, while the dye of the present invention has excellent pH sensitivity, it easily decomposes when the pH exceeds 7 and exceeds 9, so cotton stains in T/C blend dyeing can be easily removed by alkaline washing. It has the advantage of In addition, alkaline resist dyeing is also possible in textile printing. Moreover, one kind or two or more kinds of dyes represented by the general formula () can be used. In particular, when two or more types are used in combination, a dyed product with excellent build-up properties can be obtained. In carrying out the present invention, one or more dyes represented by the general formula () are ground into fine particles and dispersed in an aqueous medium together with a suitable dispersant. The dispersed dye is used in the form of a paste or in the form of a powder by spray drying or the like. Using the dye composition thus obtained, hydrophobic fibers are immersed in an aqueous medium and dyed under pressure at 105°C or higher, preferably from 110 to 140°C. It is also possible to dye at a relatively high temperature, for example in the boiling state of water, in the presence of a carrier such as O-phenylphenol or trichlorobenzene. In addition, the dye dispersion is printed on cloth and heated at 150 to 230℃.
So-called thermosol dyeing, which involves dry heat treatment for 30 to 60 seconds, is also possible. On the other hand, in the case of textile printing, a dye dispersion is kneaded with a suitable sizing agent, and this is printed on cloth, followed by steaming or thermosol treatment to dye it. Further, a solvent dyeing method using an organic solvent such as trichlorethylene or perchloroethylene as a dyeing medium is also possible. Next, the case where the compound of the present invention is used as a coloring agent for synthetic resin will be explained. In the present invention, synthetic resins include resins such as polystyrene, polyester, polyacrylate, polyolefin, polyacrylonitrile, polyvinyl chloride, polyamide, polycarbonate, and polyacetal, as well as acrylonitrile-styrene copolymers ( AS resin), acrylonitrile-butadiene-styrene copolymer (ABS resin), etc. The coloring of these resins can be achieved by blending a predetermined amount of a methine compound represented by the general formula () with the synthetic resin, kneading it, and then molding it by any method such as compression molding, injection molding, calendar molding, or extrusion molding. It can be processed into molded products such as films, plates, and pipes by processing methods, and a durable purple to green synthetic resin can be obtained. In the present invention, in addition to the compound of the general formula (), organic pigments such as isoindolinone yellow and quinoline yellow quinacridone red, inorganic pigments such as carbon black, Bengara, titanium oxide, calcium carbonate, and barium sulfate, and firefly. Photo brighteners, metal soaps, wax lubricants, etc., ultraviolet absorbers,
Favorable results can also be obtained by adding or using one or more substances such as known colorants and additives such as oxidation stabilizers in appropriate proportions as a mixed combination. According to the method of the present invention, molded products such as films, plates, and pipes made of synthetic resin have light resistance, heat resistance,
It is possible to provide a vivid purple to green color with excellent color fastness such as color migration resistance. Examples will be described below, but the method of the present invention is not limited thereto. In addition, "parts" in the examples represent "parts by weight." Example 1 In 15 parts of xylene, the formula 3.1 parts of dialdehyde represented by the following formula (A) 2.3 parts of the dicyano compound represented by the formula and 0.2 part of acetic acid were charged, and the mixture was heated under reflux at 130°C for 3 hours. After washing with methanol and then water, dry. 6.1 parts of the compound of formula (1) was obtained. [Dyeing] A dye obtained by mixing 3 parts of the dye of formula (1) with 4 parts of a formalin condensate of naphthalene-β-sulfonic acid, 3 parts of sodium ligninsulfonic acid and 20 parts of water, and milling in a ball mill for 20 hours. Spray dry the dispersion to obtain 10 parts of dye. 1 part of the dye thus obtained is added to 3000 parts of water together with 100 parts of spun polyester yarn and dyed for 60 minutes at 130 DEG C. under pressure. After dyeing,
After washing with hot water, further reduction washing, and drying, a bright and durable blue dyed product with excellent color value was obtained. Example 2 In 20 parts of ethanol, the following formula 3.4 parts of the dialdehyde shown above, 2.3 parts of the dicyano compound shown in (A) above, and 0.5 part of piperidine were charged and heated under reflux for 2 hours. After cooling, the mixture was filtered under suction, washed, and dried to obtain 6.2 parts of the compound of formula (2). When a dye bath was prepared using this dye and dyeing was carried out in the same manner as in Example 1, a dyed product with a high density, clear and solid blue color was obtained. Example 3 In 20 parts of monochlorobenzene, the following formula 4.1 parts of the dialdehyde shown above, 2.3 parts of the dicyano compound shown in (A) above, and 0.5 part of piperidine were charged and heated for 4 hours. After cooling, it is suctioned, washed and dried. 6.3 parts of the compound of formula (3) was obtained. [Coloring of synthetic resin] After heating and mixing 0.2 parts of the compound represented by the above formula (3) in fine powder form and 100 parts of powdered ABS resin at 120°C,
Create pellets through an extruder. This was then molded using an injection molding machine at 230°C. light,
A bright blue molded product with excellent heat and migration fastness was obtained. Pellets were prepared and molded in the same manner as above except that 0.5 part of titanium oxide was added to 0.2 part of the coloring agent of compound (3). A solid, pale blue colored molded product was obtained. Examples 4 to 10 Polyester fibers were dyed or printed in the same manner using the dyes shown in the following table instead of the dyes in Example 1 to obtain fast dyed products with the hues shown in the right column.

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Claims (1)

[Claims] 1 General formula () [In the formula, R ₁ and R ₂ are independently a halogen atom, a cyano group or a lower alkyl group optionally substituted with a lower alkoxy group, R ₃ and R ₄ are independently a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a hydroxy group or a lower alkanoylamino group, R ₅ and R ₆ are each independently a hydrogen atom, a halogen atom, a hydroxy group,
Cyano group, nitro group, lower alkoxy group, lower alkyl group, C ₁ - C ₆ alkoxy or phenoxycarbonyl group, carbamoyl group optionally substituted with lower alkyl or phenyl, C ₁ -
C ₆ alkyl or phenylcarbonyloxy group or lower alkoxy or phenoxycarbonyloxy group, Y represents a C ₂ -C ₁₀ alkylene group. ] A methine compound represented by 2 General formula () [In the formula, R ₁ and R ₂ are independently a halogen atom, a cyano group or a lower alkyl group optionally substituted with a lower alkoxy group, R ₃ and R ₄ are independently a hydrogen atom, a halogen atom, A lower alkyl group, a lower alkoxy group, a hydroxy group or a lower alkanoylamino group, and Y represents a C ₂ -C ₁₀ alkylene group. ] Compound represented by and general formula () [In the formula, R ₅ is substituted with a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, a lower alkoxy group, a lower alkyl group, a C ₁ to _{C 6} alkoxy or phenoxycarbonyl group, a lower alkyl or phenyl group] represents a carbamoyl group, a _C1 - _C6 alkyl or phenylcarbonyloxy group, or a lower alkoxy or phenoxycarbonyloxy group, which may be ] and general formula () [In the formula, R ₆ is substituted with a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, a lower alkoxy group, a lower alkyl group, a C ₁ to _{C 6} alkoxy or phenoxycarbonyl group, a lower alkyl or phenyl group] represents a carbamoyl group, a _C1 - _C6 alkyl or phenylcarbonyloxy group, or a lower alkoxy or phenoxycarbonyloxy group, which may be ] A general formula () characterized by reacting with a compound represented by [In the formula, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ and Y have the above meanings. ] A method for producing a methine compound shown by. 3 General formula () [In the formula, R ₁ and R ₂ are independently a halogen atom, a cyano group or a lower alkyl group optionally substituted with a lower alkoxy group, R ₃ and R ₄ are independently a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a hydroxy group or a lower alkanoylamino group, R ₅ and R ₆ are each independently a hydrogen atom, a halogen atom, a hydroxy group,
Cyano group, nitro group, lower alkoxy group, lower alkyl group, C ₁ - C ₆ alkoxy or phenoxycarbonyl group, carbamoyl group optionally substituted with lower alkyl or phenyl, C ₁ -
C ₆ alkyl or phenylcarbonyloxy group or lower alkoxy or phenoxycarbonyloxy group, Y represents a C ₂ -C ₁₀ alkylene group. ] A method for coloring an organic polymer material, the method comprising using one or more methine compounds shown below.