Magenta dye and its preparation method and use

A dye, magenta technology, applied in the field of magenta dye and its preparation, can solve the problems that magenta dye cannot meet the hue, vividness, light fastness, water resistance, ozone resistance, solubility and solution stability, etc.

Active Publication Date: 2016-06-29
DALIAN UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The invention provides a magenta dye to solve the technical problem that the existing magenta dye cannot meet the multi-faceted requirements of hue, brilliance, light resistance, water resistance, ozone resistance, solubility and solution stability

Method used

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  • Magenta dye and its preparation method and use
  • Magenta dye and its preparation method and use
  • Magenta dye and its preparation method and use

Examples

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preparation example Construction

[0071] The preparation of general formula (I) compound and mixture thereof:

[0072] When preparing the compound of the present invention, different from the prior art using non-dye compounds as starting materials to prepare other anthrapyridone sulfonic acid compounds, the present invention uses low-cost anthraquinone dye derivatives with sulfonic acid groups (III ) or (III') as the basic raw material, in an organic solvent, undergoes a ring-forming reaction with a malonate diester to form an intermediate compound (IV), and then undergoes sulfonation, hydrolysis and benzylation reactions to form a general formula ( I) Compounds, salted out or salt converted to form salts, then isolated and desalted to obtain pure compounds of formula (I).

[0073]

[0074] R in malonate diester and general formula (IV) compound 8 from C 1 -C 4 Alkyl, more preferably methyl and ethyl.

[0075] The synthesis of the compound of general formula (IV) is to make the compound of formula (III)...

Embodiment 1

[0172] (1) Put 100 parts of meta C.I. reactive blue 19, 490 parts of water into the reactor, stir evenly, and then heat to 55°C-60°C. Acid will be generated during the reaction, and the reaction will be promoted by neutralizing the generated acid with a dilute sodium hydroxide solution to keep the pH of the reaction solution at 8.5-9.0. When the pH of the reaction solution remains substantially constant, the reaction is complete. HPLC (high performance liquid chromatography) can also be used to determine if the reaction is complete. After the completion of the reaction, adjust the pH to 9.0 and stir for 1 hour. At this time, a large amount of solids will precipitate, and the precipitated solids are the (III'-RB19) compound. The resulting solid was filtered and dried. Thus, a blue-purple powder of compound (III'-RB19) was obtained in a yield of 83.1 parts. Mass spectrometry: III'-RB19: m / z (-): 483.2 ([ M -H] -1 ). The most abundant and accurate molecular mass of the inte...

Embodiment 2

[0180] Heat the partial aqueous solution of compound Dm1 (containing 9.9 parts of Dm1 dye) obtained in Example 1 to 75°C-80°C, adjust the pH to 9.0, add 9.0 parts of benzyl chloride dropwise within half an hour, and react for 3 hours; then use it for 5 minutes Add 4.5 parts of benzyl chloride dropwise for 2 hours, then add 4.5 parts of benzyl chloride dropwise for 5 minutes, and react for 4 hours. During the whole reaction process, the pH was adjusted to 9.0 with dilute sodium hydroxide solution. After the reaction was completed, 40 parts of sodium chloride was added with stirring to carry out salting out, stirred for 1 hour, and left to stand for 2 hours. The resulting product was filtered and dried, whereby a mixture of sodium salts of the Dm3 compound was obtained as a red powder in a yield of 11.2 parts. The sodium salt mixture has an absorption maximum at 536 nm (in aqueous solution). Mass spectrometry m / z (3-): 259.6 ([ M -3H] -3 ), m / z (2-): 390.2 ([ M -2H] -2 ). ...

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Abstract

The present invention relates to a kind of magenta dye and its preparation method and application. Magenta dyes, including compounds of general formula (I) or mixtures thereof that simultaneously introduce carboxyl, sulfonic acid and carbopropyl sulfone sulfonic acid on the anthrapyridone parent: In general formula (I), A can be cation M 4 or substituted or unsubstituted benzyl or substituted or unsubstituted naphthylmethyl; M 1 , M 2 , M 3 Is an independent cationic or cationic group; sulfonic acid group (SO 3 m 2 )m can be located at any position of the benzene ring, wherein m is an integer of 0-2. Due to the carboxyl group (or carboxybenzyl ester group or naphthyl methyl ester) group, sulfonic acid group, and carbonyl propyl sulfone group at the same time, the magenta dye can meet the hue, vividness, light resistance, water resistance, ozone resistance and There are many requirements for solubility and solution stability.

Description

technical field [0001] The present invention relates to a kind of magenta dye and its preparation method and application. In particular, it relates to a compound having both a sulfonic acid group and a carboxyl group on an anthrapyridone ring, or a salt thereof, or an ester thereof, or a mixture thereof, and use thereof as a magenta colorant. Background technique [0002] Among various color recording methods, the inkjet printing method is one of typical methods thereof. Because the nozzle of inkjet printing is not in contact with the recording material, it is silent and quiet, and it is easy to achieve miniaturization, high speed, and colorization. As a result, it has developed rapidly in recent years. [0003] Unlike traditional pen inks, inkjet inks are required to have high-density printed images, no nozzle clogging, good drying on recording materials, less penetration, and storage stability. There are higher standards for fastness to water resistance, moisture resist...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B5/14C09D11/328
CPCC09B5/14C09D11/02C09D11/328
Inventor 彭孝军李世玉吴金河孟凡明张蓉樊江莉王风李少磊
Owner DALIAN UNIV OF TECH
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