阅读说明：本技术 含有颜料衍生物的偶氮颜料分散体和涂膜形成用着色组合物 (Azo pigment dispersion containing pigment derivative and coloring composition for forming coating film ) 是由 山地健太 于 2020-03-05 设计创作，主要内容包括：提供抑制亮度的降低、与现有的对比度相比能够提高对比度的偶氮颜料分散体和含有该偶氮颜料分散体的涂膜形成用着色组合物。含有偶氮颜料、下述式(1)所示的颜料衍生物、分散剂和溶剂的偶氮颜料分散体以及含有该颜料分散体和涂膜形成成分的涂膜形成用着色组合物。(式(1)中,R<Sup>1</Sup>～R<Sup>4</Sup>独立地表示氢原子或卤原子,R<Sup>5</Sup>表示下述式(1-1)或式(1-2)所示的基团。n是大于0且为2以下的实数。)(式(1-1)中,Q<Sup>1</Sup>表示氢原子、卤原子或烷氧基,Q<Sup>2</Sup>表示氢原子、卤原子或烷氧基,Q<Sup>3</Sup>表示碳原子数1～4的烷基。＊表示价键。)(式(1-2)中,＊表示价键。)<Image he="142" wi="700" file="DDA0002400839060000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(Provided are an azo pigment dispersion which can suppress a decrease in brightness and can improve contrast compared with conventional contrast, and a coloring composition for forming a coating film containing the azo pigment dispersion. Containing azo pigmentsA pigment dispersion comprising a pigment derivative represented by the following formula (1), a dispersant and a solvent, and a coloring composition for forming a coating film, which comprises the pigment dispersion and a coating film-forming component. (in the formula (1), R 1 ～R 4 Independently represents a hydrogen atom or a halogen atom, R 5 Represents a group represented by the following formula (1-1) or formula (1-2). n is a real number greater than 0 and 2 or less. ) (in the formula (1-1), Q 1 Represents a hydrogen atom, a halogen atom or an alkoxy group, Q 2 Represents a hydrogen atom, a halogen atom or an alkoxy group, Q 3 ＊ represents a C1-4 alkyl group (in the formula (1-2), ＊ represents a bond.))

1. An azo pigment dispersion characterized by:

comprising an azo pigment, a pigment derivative represented by the following formula (1), a dispersant and a solvent,

in the formula (1), R¹～R⁴Independently represents a hydrogen atom or a halogen atom, R⁵Represents a group represented by the following formula (1-1) or formula (1-2), and n is more than 0 and 2 or lessThe real number of (2) is,

in the formula (1-1), Q¹Represents a hydrogen atom, a halogen atom or an alkoxy group, Q²Represents a hydrogen atom, a halogen atom or an alkoxy group, Q³An alkyl group having 1 to 4 carbon atoms, ＊ represents a bond,

in the formula (1-2), the symbol represents a valence bond.

2. The azo pigment dispersion according to claim 1, wherein:

the azo pigment contains a reaction product of a base represented by the following formula (2) and a coupling agent represented by the following formula (3) in an amount of 80% by weight or more based on the solid content,

in the formula (2), R⁶Represents R⁸-NH-C (═ O) -, group, R⁷Represents a halogen atom or R⁹A group represented by O-, R⁸Represents a hydrogen atom or a phenyl group (-C)₆H₅)，R⁹Represents an alkyl group having 1 to 4 carbon atoms,

in the formula (3), R¹⁰Represents a hydrogen atom or R¹¹-NH-C (═ O) -, group, R¹¹Represents a group represented by the following formula (3-1),

in the formula (3-1), R¹²Represents R¹⁴-NH-C (═ O) -or R¹⁴-C (═ O) -NH-, a group represented by R¹³Represents a hydrogen atom, a halogen atom or R¹⁵A group represented by O-, R¹⁴Represents a hydrogen atom or a phenyl group (-C)₆H₅)，R¹⁵Represents an alkyl group having 1 to 4 carbon atoms, and ＊ represents a bond.

3. The azo pigment dispersion according to claim 2, wherein:

the azo pigment comprises a reaction product of a substrate represented by the above formula (2) or (4) and a coupling agent represented by the above formula (3) or (5), wherein the content of the reaction product represented by the above formula (2) or (3) is 80 to 95% by weight based on the solid content,

in the formula (5), R¹⁶represents-SO₃H or-COOH.

4. The azo pigment dispersion according to claim 3, wherein:

the weight ratio of the component derived from formula (2) to the component derived from formula (4) is 90.6/9.4 to 98.9/1.1 in terms of (2)/(4), and the weight ratio of the component derived from formula (3) to the component derived from formula (5) is 82.4/17.6 to 96.5/3.5 in terms of (3)/(5).

5. The azo pigment dispersion according to any one of claims 1 to 4, wherein:

the average primary particle size of the azo pigment is 25-70 nm.

6. A coloring composition for forming a coating film, characterized in that:

comprising the azo pigment dispersion according to any one of claims 1 to 5 and a coating film-forming ingredient.

Technical Field

The present invention relates to an azo pigment dispersion containing a pigment derivative and a coloring composition for forming a coating film containing the azo pigment dispersion.

Background

Azo pigments are widely used as colorants such as paints, offset printing inks, gravure printing inks, color toners, recording inkjet inks, and colorants for color filters. In order to improve various characteristics such as brightness and contrast of a coating film formed in these applications, a finely divided azo pigment is sometimes used. However, it is generally known that a colored composition containing a finely divided pigment tends to have poor dispersion stability. Therefore, proposals have been made to improve these various properties while ensuring dispersion stability of pigments and the like (patent documents 1 to 5).

Patent document 1 describes: in the production of a red pigment dispersion for a color filter, which contains an organic pigment, a pigment dispersion aid A which is a sulfonated compound having the same skeleton as the organic pigment, a pigment dispersion aid B having a specific structure, a pigment dispersant, and an organic solvent, the following steps are performed: after the dispersion aid a and the organic pigment are mixed and subjected to a micronization treatment, the pigment dispersion aid B, the pigment dispersant and the organic solvent are mixed and subjected to a dispersion treatment. It is considered that the use of 2 pigment dispersing aids in this way improves the fine dispersibility of the pigment and the subsequent dispersion stability, and enables the achievement of excellent color characteristics, high transmittance, and contrast.

Patent document 2 describes a coloring composition for a color filter, which is characterized by comprising: a colorant (A) containing a red azo pigment (a1) having a maximum refractive index of 1.8 or less in a light wavelength region of 600 to 700 nm; and a resin (B). When such a pigment (a1) is contained, the contrast ratio is high, but the pigment does not need to be excessively finely divided, and therefore, the stability is also excellent.

Patent document 3 describes the following method: a pigment dispersion aid having a specific structure, an acrylic block copolymer having a tertiary amino group and/or a quaternary ammonium group, and an organic solvent are added to fine particles obtained by fine-pulverizing a pigment containing c.i. pigment red 221, and a pigment dispersion is obtained by dispersion, and then a red pigment dispersion resist composition for a color filter is prepared. By this method, the dispersion stability of the fine particles of the pigment containing c.i. pigment red 221 can be significantly improved as compared with the prior art, and a red pigment dispersion resist composition for a color filter excellent in dispersion stability, tinting strength, contrast, brightness, heat resistance and solvent resistance can be provided.

Patent document 4 describes: by surface-treating the naphthol red having the specific structure with a hydrophilic naphthol derivative or a hydrophilic phenol derivative having the specific structure, a naphthol red having excellent dispersibility, color developability, and transparency can be obtained.

Disclosure of Invention

Technical problem to be solved by the invention

For example, in the field of display devices using color filters, the market for high image quality is strongly demanded, and even if the inventions described in patent documents 1 to 4 are adopted, there is still room for improvement. For example, even if the contrast of the coating film can be improved, the brightness may be reduced. The object of the invention is therefore: provided are an azo pigment dispersion which can suppress a decrease in brightness and can improve contrast compared with conventional contrast, and a coloring composition for forming a coating film containing the azo pigment dispersion.

Technical solution for solving technical problem

The present inventors have conducted intensive studies in order to solve the above-mentioned technical problems. As a result, they have found that the use of a specific pigment derivative can suppress the decrease in brightness of a coating film containing the obtained pigment dispersion and can improve the contrast as compared with the conventional contrast, and have completed the present invention.

The first invention of the present invention relates to an azo pigment dispersion containing an azo pigment, a pigment derivative represented by the following formula (1), a dispersant and a solvent.

(in the formula (1), R¹～R⁴Independently represents a hydrogen atom or a halogen atom, R⁵Represents a group represented by the following formula (1-1) or formula (1-2). n is a real number greater than 0 and 2 or less. )

(in the formula (1-1), Q¹Represents a hydrogen atom, a halogen atom or an alkoxy group, Q²Represents a hydrogen atom, a halogen atom or an alkoxy group, Q³＊ represents an alkyl group having 1 to 4 carbon atoms and represents a bond

(in the formula (1-2), symbol represents a valence bond.)

Wherein, in the formulae (1-1) and (1-2), the symbol "represents a valence bond" means that the terminal represented by the symbol "means that the terminal is directly bonded to a nitrogen atom.

In the embodiment of the present invention, the azo pigment may contain 80% by weight or more (based on the solid content) of a reaction product of the substrate represented by the following formula (2) and the coupling agent represented by the following formula (3).

(in the formula (2), R⁶Represents R⁸-NH-C (═ O) -, group, R⁷Represents a halogen atom orR⁹O-is a group represented by. R⁸Represents a hydrogen atom or a phenyl group (-C)₆H₅)。R⁹Represents an alkyl group having 1 to 4 carbon atoms. )

(in the formula (3), R¹⁰Represents a hydrogen atom or R¹¹-NH-C (═ O) -. R¹¹Represents a group represented by the following formula (3-1). )

(in the formula (3-1), R¹²Represents R¹⁴-NH-C (═ O) -or R¹⁴-C (═ O) -NH-, a group represented by R¹³Represents a hydrogen atom, a halogen atom or R¹⁵O-is a group represented by. R¹⁴Represents a hydrogen atom or a phenyl group (-C)₆H₅)。R¹⁵＊ represents an alkyl group having 1 to 4 carbon atoms and represents a bond

Wherein, in the formula (3-1), ＊ represents a bond means that the terminal represented by "＊" is directly bonded to the nitrogen atom, that is, R¹⁰Is R¹¹when-NH-C (═ O) -represents a group, R¹⁰Is a group represented by the following formula (3-2). In the formula (3-2), R¹²、R¹³As described above.

In an embodiment of the present invention, the azo pigment contains a reaction product of a base represented by the above formula (2) or (4) and a coupling agent represented by the above formula (3) or (5), and the content (based on solid content) of the reaction product of the formula (2) or (3) may be 80 to 95% by weight.

(in the formula (5), R¹⁶represents-SO₃H or-COOH, or a group represented by-COOH. )

In an embodiment of the present invention, the weight ratio ((2)/(4)) of the component derived from formula (2) to the component derived from formula (4) may be 90.6/9.4 to 98.9/1.1, and the weight ratio ((3)/(5)) of the component derived from formula (3) to the component derived from formula (5) may be 82.4/17.6 to 96.5/3.5.

In an embodiment of the present invention, the azo pigment may have an average primary particle diameter of 25 to 70 nm.

The second invention of the present invention relates to a coloring composition for forming a coating film, which contains the azo pigment dispersion and a coating film-forming component.

According to the present invention, an azo pigment composition which can suppress a decrease in brightness and can improve contrast compared with conventional contrast, and a method for producing the azo pigment composition can be provided.

Detailed Description

Embodiments of the present invention will be described below.