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

Patent metadata

Field	Value
Publication number	US-2016333202-A1
Application number	US-201415110056-A
Country	US
Kind code	A1
Filing date	Feb 19, 2014
Priority date	Feb 19, 2014
Publication date	Nov 17, 2016
Grant date	—

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

1 . A near infrared-reflecting/transmitting azo pigment exhibiting a near infrared-reflecting/transmitting property,
the 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 a diazonium compound of a compound represented by formula (1) is used as a diazo component, and the azo pigment is obtained by coupling the diazo component with any one of coupling components selected from the group consisting of compounds represented by formulas (2), (3), and (4):

wherein R 1 to R 3 in the formulas (2) to (4) each independently represent any one of a hydrogen atom, a halogen atom, a methyl group, a methoxy group, an ethoxy group, and an acetylamino group.

2 . The near infrared-reflecting/transmitting azo pigment according to claim 1 , wherein an L* value in a CIE LAB (L*a*b*) color system is 10 or more when color measurement of a paint applied on white paper with a 10-mill applicator, the paint prepared by adding the azo pigment so as to be 10 parts by mass to 100 parts by mass of a solid content of a melamine alkyd resin and dispersing the azo pigment is conducted with a spectrophotometer.

3 . A process for producing the 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 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 diazo component; a step of using any one selected from the group consisting of compounds represented by formulas (2), (3), and (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 an organic solvent having a boiling point of 120° C. or higher to conduct coupling reaction, thereby synthesizing an azo pigment; and a step of subsequently heating the organic solvent containing the synthesized azo pigment at a temperature of 120° C. to 200° C. while distilling (removing) a component (liquid) 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 (crystallizing) the azo pigment in the organic solvent having a boiling point of 120° C. or higher:

wherein R 1 to R 3 in the formulas (2) to (4) each represent any one of a hydrogen atom, a halogen atom, a methyl group, a methoxy group, an ethoxy group, and an acetylamino group.

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

5 . 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 near infrared-reflecting/transmitting azo pigment according to claim 1 , or the pigment component is the near infrared-reflecting/transmitting azo pigment obtained by a process comprising: a step of dispersing 3-(4-aminophenylimino)-1-oxo-4,5,6,7-tetrachloroisoindoline represented by 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 diazo component; a step of using any one selected from the group consisting of compounds represented by formulas (2), (3), and (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 an organic solvent having a boiling point of 120° C. or higher to conduct coupling reaction, thereby synthesizing an azo pigment; and a step of subsequently heating the organic solvent containing the synthesized azo pigment at a temperature of 120° C. to 200° C. while distilling (removing) a component (liquid) 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 (crystallizing) the azo pigment in the organic solvent having a boiling point of 120° C. or higher:

wherein R 1 to R 3 in the formulas (2) to (4) each represent any one of a hydrogen atom, a halogen atom, a methyl group, a methoxy group, an ethoxy group, and an acetylamino group.

6 . The coloring agent composition according to claim 5 , wherein the liquid dispersion medium comprises a film-forming component,
the film-forming component is at least one 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 the film-forming component comprises a solvent and/or water to be in a liquid form.

7 . The coloring agent composition according to claim 5 , wherein the solid dispersion medium is a dispersion medium in a solid form, the solid dispersion medium comprising at least one solid dispersion 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.

8 . The coloring agent composition according to claim 5 , wherein the coloring agent composition is for use in any one of paints, plastics, synthetic fibers, printing inks, and writing materials, or the coloring agent composition is for coloration in image recording or image displaying.

9 . A coloring method for coloring an article having a transparent base material using the coloring agent composition according to claim 8 , wherein a surface of the transparent base material is colored using the coloring agent composition by any one of methods selected from the group consisting of painting, 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 for forming the coloring agent composition or impregnating the coloring agent composition into a material for forming the coloring agent composition.

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

Assignees

• Dainichiseika Color Chem

Inventors

• Okamoto Hisao
• Ito Hideki
• Yanagimoto Hiromitsu

Classifications

• C09D11/322

  Pigment inks · CPC title

• C09D11/037 Primary

  characterised by the pigment · CPC title

• C09D5/32

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

• C09B56/02 Primary

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

• C09B29/33

  Aceto- or benzoylacetylarylides · CPC title