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Diketopyrrolopyrrole polyether derivative and preparation method thereof

The technology of diketopyrrolopyrrole polyether and diketopyrrolopyrrole is applied to the derivatives of high-grade pigment diketopyrrolopyrrole series pigments and the field of preparation thereof, and can solve the problem of large molecular weight, poor water solubility and dispersibility, and no surface Activity and other issues, to achieve the effect of high color strength, good dispersion and application performance, good solubility and surface activity

Inactive Publication Date: 2018-03-27
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Patent CN201410721316.X introduces a method for preparing an asymmetric diketopyrrolopyrrole derivative organic photosensitive dye. This kind of DPP derivative has complex molecular structure, large molecular weight, poor water solubility and dispersibility, and almost no surface activity at all.

Method used

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  • Diketopyrrolopyrrole polyether derivative and preparation method thereof
  • Diketopyrrolopyrrole polyether derivative and preparation method thereof
  • Diketopyrrolopyrrole polyether derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] (1)

[0036]

[0037] Add polyethylene glycol monomethyl ether (10) compound (produced by Zhongshan Chemical Company) and toluene in a four-necked flask equipped with a condenser tube and a water separator, heat to reflux, and remove polyethylene glycol monomethyl ether (10) compound moisture in. The polyethylene glycol monomethyl ether (10) compound was isolated by rotary evaporation.

[0038] In the round bottom flask, add polyethylene glycol monomethyl ether (10) compound (0.01mol, 4.72g) and pyridine 20ml after dehydration treatment, slowly add thionyl chloride (0.03mol, 0.03mol, 3.57 g), after the dropwise addition, continue to stir at room temperature for 24 hours, and wash with ether 3 times to obtain the product chloropolyethylene glycol monomethyl ether (10), the structural formula of which is CMPEG-1 as shown above.

[0039] (2)

[0040]

[0041] In a four-necked flask equipped with a condenser tube, add DMF (30ml), while stirring, add DPP pigment red...

Embodiment 2

[0043]

[0044] Except that pigment red 254 (0.01mol, 3.56g) was used to replace pigment red 255 in the example, the other steps were the same as in example 1 to obtain the product shown in formula P-2 with a yield of 92%. Product P-2 proton magnetic resonance detection results, 1 HNMR (CDCl 3 , 500MHz) δ (ppm): 3.24 (s, 3H), 3.510-3.56 (m, 40H), 7.22 (d, 2H), 7.26 (d, 2H).

Embodiment 3

[0046] (1)

[0047]

[0048] Add polyethylene glycol monomethyl ether (20) compound (produced by Zhongshan Chemical Co.) and toluene in a four-necked flask equipped with a condenser tube and a water separator, heat to reflux, and remove polyethylene glycol monomethyl ether (20) compound moisture in. The polyethylene glycol monomethyl ether (20) compound was isolated by rotary evaporation.

[0049] In the round bottom flask, add polyethylene glycol monomethyl ether (20) compound (0.01mol, 9.12g) and pyridine 30ml after dehydration treatment, slowly add thionyl chloride (0.03mol, 0.03mol, 3.57 g), after the dropwise addition, continue to stir at room temperature for 24 hours, and wash 3 times with ether to obtain the product chloropolyethylene glycol monomethyl ether (20), the structural formula of which is CMPEG-2 as shown above.

[0050] (2)

[0051]

[0052] In a four-necked flask equipped with a condenser tube, add DMF (30ml), and add DPP pigment 3,6-bis(4-morpholine ...

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Abstract

The invention relates to a diketopyrrolopyrrole polyether derivative and a preparation method thereof. The preparation method for the diketopyrrolopyrrole polyether derivative comprises the followingsteps: (1) reacting polyethylene glycol monomethyl ether with thionyl chloride to produce chlorinated polyethylene glycol monomethyl ether; and (2) reacting chlorinated polyethylene glycol monomethylether prepared in the step (1) with a variety of DPP compounds so as to prepare the target diketopyrrolopyrrole polyether derivative. The DPP pigment derivative of the invention has good water-solubility, surface activity and emulsification and dispersing capabilities, can be used as an additive for post-treatment of crude DPP pigment products, and is applicable as a dispersant and emulsifier forpreparation of color paste and paint from DPP pigments.

Description

technical field [0001] The invention belongs to the field of organic pigments and high-grade coatings, and relates to derivatives of high-grade pigment diketopyrrolopyrrole (DPP) series pigments and a preparation method thereof. technical background [0002] Diketopyrrolopyrrole series pigments contain 1,4-diketopyrrolopyrrole structure in their molecules, which is 1,4-Diketopyrrolo-[3,4-C]Pyrroles in English, so it is also called DPP pigment. Its structural general formula is as follows: [0003] [0004] If different substituted phenyl groups are attached to the para-position of the 1,4-diketopyrrolopyrrole ring carbonyl, a series of DPP pigments are formed, and the colors range from orange, red to bluish red. [0005] DPP pigments have bright colors, excellent durability, high tinting strength, good fluidity and chemical stability. At the same time, due to the existence of large intermolecular hydrogen bonds and coplanarity, it has excellent solvent resistance, migra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C09B57/00C08G65/48
CPCC07D487/04C08G65/48C09B57/004
Inventor 孙戒
Owner NANJING UNIV OF TECH