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Pigment derivative, preparation method thereof, pigment composition containing pigment derivative and application of pigment composition

A pigment derivative and rigid technology, applied in pigment paste, chemical instruments and methods, azo dyes, etc., can solve the problems of limited pigment particle size control ability, poor heat resistance of phthalocyanine pigment derivatives, and difficult to unite , to achieve excellent transparency, narrow particle size distribution, and not easy to agglomerate

Pending Publication Date: 2021-12-07
山东凯瑞尔光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the heat resistance of the phthalocyanine pigment derivatives prepared by it is poor, and the ability to control the particle size of the pigment is also limited.
Moreover, phthalimide-based phthalocyanine pigment derivatives have a blue phase, and use in green phase pigments will cause color deviation
[0005] Based on the above technical problems, it is necessary to develop a new type of phthalocyanine pigment composition to solve the technical problems of poor heat resistance, small particle size and difficulty in uniting organic pigments in the prior art, while having high brightness and high contrast

Method used

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  • Pigment derivative, preparation method thereof, pigment composition containing pigment derivative and application of pigment composition
  • Pigment derivative, preparation method thereof, pigment composition containing pigment derivative and application of pigment composition
  • Pigment derivative, preparation method thereof, pigment composition containing pigment derivative and application of pigment composition

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preparation example Construction

[0043] The preparation method of the pigment derivative is to firstly prepare an intermediate product containing a Q-Ar substituent group, and then halogenate the intermediate product to obtain the pigment derivative.

[0044] Wherein, the preparation method of the intermediate product containing the Q-Ar substituent group can be prepared under the action of a catalyst by phthalic anhydride substituted by rigid unit Ar or phthalonitrile and metal salt substituted by rigid unit Ar; It is prepared by connecting the rigid linking group Q to the parent phthalocyanine ring, and then reacting with the rigid unit Ar. Wherein, halogenation may be chlorination or bromination, or a combination of bromine and chlorination.

[0045] As a method for reacting phthalic anhydride substituted by rigid unit Ar with metal salts, the following can be cited: reacting a hydroxyl derivative of Ar with 4-nitrophthalimide (CAS No. 89-40-7) and potassium carbonate Add it into a polar organic solvent, ...

Embodiment 1

[0070] 1. Synthesis of Pigment Derivative 1

[0071] (1) Synthesis of zinc phthalocyanine-naphthalene

[0072]

[0073] Add 250ml of N,N-dimethylformamide (DMF), 37.83g of nitrophthalonitrile, and 34.60g of naphthol into a three-necked flask equipped with mechanical stirring, a condenser, and a thermometer, heat to 60°C, and add 66.24 g of anhydrous potassium carbonate, heated to 80°C and stirred overnight. The reacted solution was poured into water, continued to stir for 1 h, and then filtered. The filter cake was washed with 5% NaOH solution and water, and dried to obtain 52.45 g of phthalonitrile-O-naphthalene, with a yield of 96.7%.

[0074]Add 150g of n-pentanol, 14.18g of phthalonitrile, 15g of phthalonitrile-o-naphthalene into a three-necked flask equipped with mechanical stirring, condenser and thermometer, heat up to 100°C and stir to dissolve, add 6.06g of DBU , 3.40g zinc chloride, continue to heat up to 160 ℃, maintain 5h. The temperature of the system was lo...

Embodiment 2

[0092] 1. Synthesis of Pigment Derivative 2

[0093] (1) Synthesis of copper phthalocyanine-sulfonic acid fluorene

[0094]

[0095] Add 600g of chlorosulfonic acid into a three-necked flask equipped with mechanical stirring, thermometer, and condenser, start stirring, and slowly add 120g of copper phthalocyanine at 45-50°C. After the feeding is completed, the temperature is raised to 128°C, and the reaction is kept for 4 hours (sampling and monitoring), and the temperature is lowered to 60-65°C. Within 2 hours, 150g of thionyl chloride is added dropwise. After the dropwise addition, the temperature is raised to 90°C and the reaction is continued for 30 minutes. Then raise the temperature to 105°C, react for 30 minutes, and then lower the temperature to 45°C. Pour the material into ice water, control the temperature not to exceed 5° C., filter, and wash the filter cake with ice water until pH=4 or more to obtain 1080 g of filter cake with a solid content of 18%. Store the...

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Abstract

The invention discloses a pigment derivative which has a structure as shown in a general formula I. M represents 2H or a metal atom, a substituent group Q-Ar represents a rigid structural unit, Ar represents an unsubstituted or alkyl and alkoxy substituted aromatic ring and heteroaromatic ring, Ar is a rigid unit, Q represents a rigid linking group, and X1-X15 represent a hydrogen atom, a chlorine atom, a bromine atom or a Q-Ar substituent group. The invention also provides a preparation method of the pigment derivative, a pigment composition containing the pigment derivative and application of the composition. The method can effectively inhibit particle size agglomeration of the pigment, the prepared pigment composition has the advantages of narrow particle size distribution and easy dispersion, and the prepared color paste has excellent transparency, colorability and heat resistance.

Description

technical field [0001] The invention relates to the technical field of organic pigment compositions, in particular to a pigment derivative and a preparation method thereof, a pigment composition containing the same and an application thereof. Background technique [0002] Currently, organic pigment compositions are used in various fields. For example, organic pigment compositions are widely used in the fields of color filters, printing inks, paints, colorants for resins, colorants for fibers, and colorants for leather. [0003] Organic pigments used in high-functional applications such as inkjet inks and color filters for color filters require more vivid printing and higher brightness and contrast, which requires finer pigment particle sizes to achieve, usually requiring the use of A finer pigment with an average primary particle size of 100 nm or less. However, fine organic pigments are easier to aggregate, so the organic pigments need to be surface treated; in addition, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B47/067C09B47/10C09B47/24C09D17/00G02B5/20G02B5/22
CPCC09B47/0675C09B47/10C09B47/24C09D17/003G02B5/223G02B5/208
Inventor 豆帆滕福爱颜俊雄崔亨利张晓军孙兆伟朱洪维刘海燕
Owner 山东凯瑞尔光电科技有限公司
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