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Preparation method and application of chain transfer near-infrared dye and polymer emulsion thereof

A near-infrared dye and infrared dye technology are applied in the field of chain transfer near-infrared dyes and the preparation of polymer emulsions, which can solve the problems of reduced product contrast, uneven dispersion of infrared dyes, and insufficiently uniform dispersion of dyes, and improve stability. Effect

Inactive Publication Date: 2017-06-09
BEIJING INSTITUTE OF GRAPHIC COMMUNICATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] First, infrared dyes are oil-soluble dyes. When they are compounded with water-based dispersed emulsions, there are compatibility problems, which will lead to uneven and unstable dispersion of infrared dyes in water systems.
[0006] Second, after the product is formed into a film, the infrared dye will migrate in the printing plate precursor due to compatibility problems, resulting in uneven dispersion of the dye in the printing plate precursor film, resulting in unstable imaging
[0007] Third, the infrared absorbing dye and nanoparticles are separated in the system, and the photostability of the dye is poor, so that the printing plate has a certain amount of fog before exposure, and the contrast of the final product is reduced
At present, there is no report on the polymerization of infrared absorbing dyes to construct thermosensitive emulsion precursors by chain transfer reaction

Method used

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  • Preparation method and application of chain transfer near-infrared dye and polymer emulsion thereof
  • Preparation method and application of chain transfer near-infrared dye and polymer emulsion thereof
  • Preparation method and application of chain transfer near-infrared dye and polymer emulsion thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 11

[0065] Example 1 Synthesis of near-infrared dyes using 1,6-hexanedithiol as chain transfer reagent and preparation of polymerized heat-sensitive polymer emulsion

[0066] (1) Preparation of thermosensitive near-infrared dyes capable of chain transfer

[0067] Add 6 grams of near-infrared dye, 5.96 grams of 1,6-hexanedithiol and 4 grams of triethylamine into a single-port bottle, wherein, near-infrared dye: 1,6-hexanedithiol: triethylamine (molar ratio) 1 :5:5, add 50 ml of N,N dimethylformamide, stir and mix and react at 25°C under nitrogen protection for 24 hours. Centrifuge at a speed of 1 / min and collect the solid dye after drying.

[0068] Such as figure 2 Shown is the NMR image of the chain-transferable infrared dye of Example 1.

[0069] The reaction equation of above-mentioned preparation dye monomer is as follows:

[0070]

[0071] (2) Preparation of polymerized thermosensitive polymer emulsion

[0072] The oil phase is prepared by dissolving 5 grams of the ab...

Embodiment 21

[0081] Example 2 Synthesis of near-infrared dyes using 1,2-ethanedithiol as a chain transfer agent and preparation of polymerized thermosensitive polymer emulsion

[0082] (1) Preparation of thermosensitive near-infrared dyes capable of chain transfer

[0083] Add 6 grams of near-infrared dye, 7.47 grams of 1,2-hexanedithiol and 8 grams of triethylamine into a single-port bottle, wherein, near-infrared dye: 1,2-ethanedithiol: triethylamine (molar ratio) 1 :10:10, add 50 milliliters of N,N dimethylformamide, stir and mix and react for 12 hours under nitrogen protection at 25°C, after the end, add a large amount of ether to the flask for stirring and washing. Centrifuge at a speed of 1 / min and collect the solid dye after drying.

[0084] Such as image 3 Shown is the NMR map of the chain-transferable infrared dye of Example 2.

[0085] The reaction equation of above-mentioned preparation dye monomer is as follows:

[0086]

[0087] (2) Preparation of polymerized thermosen...

Embodiment 3

[0092] Example 3 Synthesis of near-infrared dyes using 2,3 dimercaptosuccinic acid as chain transfer reagent and preparation of polymerized heat-sensitive polymer emulsion

[0093] (1) Preparation of thermosensitive near-infrared dyes capable of chain transfer

[0094] Add 6 grams of near-infrared dye, 2.15 grams of 2,3 dimercaptosuccinic acid and 0.6 grams of triethylamine into a one-mouth bottle, wherein, near-infrared dye: 2,3 dimercaptosuccinic acid: triethylamine (molar ratio) 1:1.5:1.5, add 50 ml of N,N dimethylformamide, stir and mix and react at 25°C under nitrogen protection for 24 hours. Centrifuge at a speed of 1 rpm, and collect the solid dye after drying.

[0095] Such as Figure 4 Shown is the NMR image of the chain transfer infrared dye of Example 3.

[0096] The reaction equation of above-mentioned preparation dye monomer is as follows:

[0097]

[0098] (2) Preparation of polymerized thermosensitive polymer emulsion

[0099] Prepare the oil phase, diss...

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Abstract

The invention discloses a chain transfer near infrared dye and a high-molecular polymerization emulsion preparation method and application thereof. The chain transfer near infrared dye is prepared by reaction of a near infrared dye and a double functional group sulfhydryl group. The near infrared dye, a chain transfer functional reagent and a promoter are mixed in an organic solvent according to the mole ratio of 1:1-20:1-4 for reaction, the dosage of dye to solvent is 1g: 10ml to 50ml, in the reaction step, the temperature is 0-50 DEG C, and the time is 10 to 72h, after the reaction, the reaction product is separated and washed with ether, and is centrifuged at high speed of 8000-12000 revolutions per minute, and the chain transfer near infrared dye can be collected. In the process of emulsion polymerization, the chain transfer reaction can be occurred, and the high-molecular thermosensitive polymerization emulsion can be prepared. The high-molecular thermosensitive polymerization emulsion can not only improve the stability of the near infrared dye, but also can be used as a thermosensitive precursor in the field of infrared laser imaging.

Description

technical field [0001] The invention relates to the technical fields of fine chemical industry and material chemistry, in particular to a chain-transfer near-infrared dye and a preparation method and application of a polymer emulsion thereof. Background technique [0002] The lithographic printing plate is characterized by the graphic part and the blank part, there is no obvious difference in height, and they are almost on the same plane. Its function is to transfer the printing ink loaded by the graphic part to the substrate under the printing pressure, while the other part does not transfer the printing ink to form a non-graphic part. The plate-making process of lithographic printing plate is that after the printing plate is selectively exposed, the photosensitive coating undergoes photophysical and chemical changes to form an image, and a printable graphic part is obtained. Among them, the heat-sensitive plate is exposed by near-infrared laser, and the graphic part is ob...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B23/08C08F212/08C08F220/44C08F220/28C08F2/38
Inventor 安粒李仲晓蒲嘉陵
Owner BEIJING INSTITUTE OF GRAPHIC COMMUNICATION
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