Near infrared-reflecting/transmitting azo pigment, method for manufacturing near infrared-reflecting/transmitting azo pigment, colorant composition using said azo pigments, item-coloring method and colored item

Patent metadata

Field	Value
Publication number	US-9822266-B2
Application number	US-201415110056-A
Country	US
Kind code	B2
Filing date	Feb 19, 2014
Priority date	Feb 19, 2014
Publication date	Nov 21, 2017
Grant date	Nov 21, 2017

Abstract

An azo pigment is provided which can be used as a coloring agent, etc. for use in paints, plastics, synthetic fibers, printing inks, and writing materials or for image recording or image displaying and which has performance of exhibiting high near infrared reflection/transparency, particularly when used as a heat-shielding paint, even in the case where the pigment has a dark color, and as a result, colored articles having the above-described properties are provided, and furthermore an article that is also useful as a printing ink in the security field is provided particularly when the pigment has a dark or black color. Specifically, an azo pigment is provided which is obtained through coupling reaction between a particular azo component and a particular coupling component, which has a plurality of chromophores of an azomethine group and of an azo group within a molecule, and in which the diazo component is a diazotized product of 3-(4-aminophenylimino)-1-oxo-4,5,6,7-tetrachroloisoindoline.

First claim

The invention claimed is:

1. A crystalized near infrared-reflecting/transmitting azo pigment exhibiting a near infrared-reflecting/transmitting property, comprising
a crystalized azo pigment having a single maximum reflectance wavelength in a wavelength region from 600 to 900 nm in a reflectance spectrum measured on a black substrate in a wavelength region from 500 to 1500 nm,
wherein the crystalized azo pigment is obtained by coupling a diazo component, which comprises a diazonium salt, which is a salt of a diazonium compound represented by formula (1) below, with a coupling component represented by formula (4) below:

wherein R 1 , R 2 , and R 3 in the formula (4) are independently selected from the group consisting of a hydrogen atom, a halogen atom, a methyl group, a methoxy group, an ethoxy group, and an acetylamino group,
the crystalized azo pigment is formed by a process comprising: (i) preparing the diazonium component comprising the diazonium salt by using an organic solvent having a boiling point of 120° C. or higher; (ii) synthesizing an azo pigment by a coupling reaction between the diazonium component and the compound represented by the formula (4) in the organic solvent having a boiling point of 120° C. or higher; and (iii) subjecting the synthesized azo pigment to pigmentation by crystalizing the azo pigment in the organic solvent having a boiling point of 120° C. or higher, and
an L* value in a CIE LAB (L*a*b*) color system is in a range of 10 or more when color measurement of a paint applied on white paper with a 10-mill applicator is conducted with a spectrophotometer, wherein the paint is prepared by adding the crystalized azo pigment in an amount of 10 parts by mass relative to 100 parts by mass of a solid content of a melamine alkyd resin, and dispersing the azo pigment in the melamine alkyd resin.

2. A process for producing the crystalized near infrared-reflecting/transmitting azo pigment according to claim 1 , the process comprising:
a step of dispersing 3-(4-aminophenylimino)-1-oxo-4,5,6,7-tetrachloroisoindoline represented by the formula (1) in the organic solvent having a boiling point of 120° C. or higher, then preparing a hydrochloric acid salt with concentrated hydrochloric acid, and diazotizing the hydrochloric acid salt with a nitrite dissolved in water to prepare the diazonium salt, thereby preparing the diazonium component;
a step of using the compound represented by the formula (4) as the coupling component, and dropping a solution of the diazonium salt prepared in the above step into an organic solvent solution obtained by dispersing the coupling component in the organic solvent having a boiling point of 120° C. or higher and conducting the coupling reaction, and thereby synthesizing the azo pigment; and
a step of subsequently heating the organic solvent containing the synthesized azo pigment at a temperature in a range from 120° C. to 200° C., while removing a liquid component having a boiling point of 120° C. or lower from the organic solvent containing the synthesized azo pigment by distilling, thereby subjecting the azo pigment to the pigmentation by crystallizing the azo pigment in the organic solvent having a boiling point of 120° C. or higher.

3. The process for producing the crystalized near infrared-reflecting/transmitting azo pigment according to claim 2 ,
wherein the organic solvent having a boiling point of 120° C. or higher is at least one solvent selected from the group consisting of chlorobenzene, o-dichlorobenzene, ethyl cellosolve, butyl cellosolve, nitrobenzene, o-nitrotoluene, N—N-dimethylformamide, N—N-di methylacetamide, N-methyl-2-pyrrolidone, and 1,3-dimethyl-2-imidazolidinonedimethyl.

4. A coloring agent composition in a liquid or solid form, comprising a pigment component in a liquid dispersion medium or in a solid dispersion medium,
wherein the pigment component is the crystalized near infrared-reflecting/transmitting azo pigment according to claim 1 or a crystalized near infrared-reflecting/transmitting azo pigment formed by a process comprising:
a step of dispersing 3-(4-aminophenylimino)-1-oxo-4,5,6,7-tetrachloroisoindoline represented by the formula (1) in an organic solvent having a boiling point of 120° C. or higher, then preparing a hydrochloric acid salt with concentrated hydrochloric acid, and diazotizing the hydrochloric acid salt with a nitrite dissolved in water to prepare a diazonium salt, thereby preparing a diazonium component;
a step of using the compound represented by the formula (4) as a coupling component, and dropping a solution of the diazonium salt prepared in the above step into an organic solvent solution obtained by dispersing the coupling component in the organic solvent having a boiling point of 120° C. or higher and conducting a coupling reaction, and thereby synthesizing an synthesized azo pigment; and
a step of subsequently heating the organic solvent containing the synthesized azo pigment at a temperature in a range from 120° C. to 200° C., while removing a liquid component having a boiling point of 120° C. or lower from the organic solvent containing the synthesized azo pigment, thereby subjecting the azo pigment to pigmentation by crystallizing the azo pigment in the organic solvent having a boiling point of 120° C. or higher.

5. The coloring agent composition according to claim 4 ,
wherein the liquid dispersion medium comprises a film-forming component,
the film-forming component is at least one material selected from the group consisting of polymers having or not having a reactive group, oligomers having or not having a reactive group, and monomers having or not having a reactive group, and the film-forming component itself is in a liquid form or comprises a solvent or water or a mixture thereof so as to be in a liquid form.

6. The coloring agent composition according to claim 4 ,
wherein the solid dispersion medium is a dispersion medium in a solid form, and
the solid dispersion medium comprises at least one medium selected from the group consisting of solid dispersion media made of a thermoplastic resin, solid dispersion media made of a thermosetting resin, waxes, fatty acid amides, and metal soaps of a fatty acid.

7. The coloring agent composition according to claim 4 ,
wherein the coloring agent composition is present in at least one material selected from the group consisting of paints, plastics, synthetic fibers, printing inks, and writing materials, or
the coloring agent composition colors image recording or image displaying.

8. A coloring method for coloring an article having a transparent base material with the coloring agent composition according to claim 7 ,
wherein a surface of the transparent base material is colored with the coloring agent composition by at least one method selected from the group consisting of paint application, dying, printing, writing, drawing, inkjet printing, electrophotographic printing, and electrostatic printing, or
an inside of the article is colored by a method of kneading the coloring agent composition with a material forming the coloring agent composition or impregnating the coloring agent composition into a material forming the coloring agent composition.

9. A colored article colored by the method for coloring an article according to claim 8 .

10. The crystalized near infrared-reflecting/transmitting azo pigment accordingly to claim 1 ,
wherein the crystalized near infrared-reflecting/transmitting azo pigment has higher reflectance and lower transmittance in a wavelength range from 600-1500 nm, compared with reflectance and lower tran

Assignees

• Dainichiseika Color Chem

Inventors

• Okamoto Hisao
• Ito Hideki
• Yanagimoto Hiromitsu

Classifications

• C09D5/004

  Reflecting paints; Signal paints · CPC title

• C09D5/32

  Radiation-absorbing paints {(protection against X-, gamma- or corpuscular radiation G21F)} · CPC title

• C09D11/037 Primary

  characterised by the pigment · CPC title

• C09B56/02 Primary

  Azomethine-azo dyes {(1,2-Complex dyes of AZOMETHINE and AZO dyes, C09B55/001)} · CPC title

• C09D11/322

  Pigment inks · CPC title