Magenta dye and preparation method and application thereof

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: 2012-08-15
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 preparation method and application thereof
  • Magenta dye and preparation method and application thereof
  • Magenta dye and preparation method and application thereof

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 invention relates to a magenta dye and a preparation method and application thereof. The magenta dye comprises a compound with a general formula (I) or mixture thereof, wherein the carboxyl, sulfonyl and carbonyl propyl sulfonyl sulfonic acid are simultaneously introduced to the anthracene pyridone parent; A in the general formula (I) can be cation M4 or substituted or un-substituted benzyl or substituted or un-substituted naphthyl methyl; M1, M2 and M3 are independent cation or anion groups; and the sulfonic acid group (SO3M2) m can be located at any position of the benzene ring, wherein m is an integer from 0-2. The magenta dye contains carboxyl (or carboxyl benzyl ester group or naphthyl methyl) group, sulfonic acid group and carbonyl propyl sulfonyl, thus the magenta dye can meet the requirements for multiple aspects of tone, vividness, light resistance, water resistance, ozone resistance, dissolubility 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 Applications(China)
IPC IPC(8): C09B5/14C09D11/02C09D11/328
CPCC09D11/328C09B5/14C09D11/02
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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