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A kind of thioxanthone dicarboxamide compound and its preparation method and application

A thioxanthone dicarboxamide and xanthone dicarboxamide technology are applied in the field of thioxanthone dicarboxamide compounds and their preparation, achieving high photo-initiating activity, good ultraviolet absorption capacity, and improving photo-initiating efficiency Effect

Active Publication Date: 2018-10-19
广州纽楷美新材料科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, UV-LED photoinitiators with high polymerization rates have not been reported yet

Method used

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  • A kind of thioxanthone dicarboxamide compound and its preparation method and application
  • A kind of thioxanthone dicarboxamide compound and its preparation method and application
  • A kind of thioxanthone dicarboxamide compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1: 1,2-thioxanthone diamide carboxylic acid (TX-COOH)

[0050] Take a 250ml round bottom flask, add 1,2-thioxanthone diacid anhydride (0.4760g, 1.69mmol), dissolve it in 220ml glacial acetic acid under heating, add 0.2651g (1.69mmol) tranexamic acid, and react at 123°C under reflux for 3h. After cooling to room temperature, standing overnight to precipitate a precipitate, filtering, washing with xylene, and drying in vacuum to obtain a yellow crystal product with a yield of 66.1%. 1 H NMR(300MHz, DMSO-d 6 ): δ 1.05 (m, 2H), 1.23 (m, 2H), 1.73 (m, 3H), 1.90 (m, 2H), 2.14 (m, 1H), 3.44 (d, 2H), 7.63 (t, 1H),7.82(t,1H),7.95(t,2H),8.44(d,1H),8.80(d,1H).IR(KBr,cm -1 ):734(υ C-S ),927,1400(υ O=H ),1590(υ C=C ),1640,1773(υ C=O ).Anal.Calcd.for C 23 H 19 NO 5 S: C, 65.54; H, 4.54; N, 3.32; S, 7.61%; Found: C, 64.34; H, 4.59; N, 3.27; S, 7.46.

[0051] Product 1 H NMR and FT-IR spectra are as figure 1 with figure 2 Shown.

Embodiment 2

[0052] Example 2: 1,2-thioxanthone diamide ethanol (TX-OH)

[0053] Add 0.423g of 1,2-thioxanthone diacid anhydride and 50ml of dioxane to a 150ml round bottom flask, stir to dissolve the reactants completely, add 20ml of 0.092g ethanolamine in dioxane solution, and react at 102°C for 3h. After cooling to room temperature, the solvent was removed by rotary evaporation, and then fully washed with ether to obtain a yellow product with a yield of 94%. 1 H NMR (DMSO): δ=8.79 (1H, d, Ha), 8.44 (1H, d, Hb), 7.95 (2H, t, Hc), 7.82 (1H, t, Hd), 7.62 (1H, t, He),3.66(4H,m,Hf).IR(KBr,cm -1 ):735(υC-S),1589(υ C=C ),1640,1765(υ C=O ),1463(υ O=H ).Anal.Calcd.forC 17 H 11 NO 4 S: C, 62.76; H, 3.41; N, 4.31; S, 9.85%; Found: C, 62.59; H, 3.49; N, 4.33; S, 9.91.

[0054] Product 1 H NMR and FT-IR spectra are as image 3 with Figure 4 Shown.

Embodiment 3

[0055] Example 3: 1,2-thioxanthone diamide thiol (TX-SH)

[0056] Add 0.282g of 1,2-thioxanthone diacid anhydride and 100ml of glacial acetic acid to a 150ml round bottom flask, heat to completely dissolve the reactants, add 0.077g mercaptoethylamine, reflux for 3h at 123°C, cool to room temperature, and let stand overnight The precipitate was separated out, filtered, washed with xylene, and dried under vacuum at 60°C to obtain a yellow crystal product with a yield of 76.2%. 1 H NMR (DMSO): δ = 8.85 (1H, d, Ha), 8.48 (1H, d, Hb), 7.99 (2H, t, Hc), 7.85 (1H, t, Hd), 7.66 (1H, t, He), 3.79(2H,m,Hf),2.78(2H,m,Hg).IR(KBr,cm -1 ):736(υ C-S ),1583(υ C=C ),1640,1767(υ C=O ),2537(υ S-H ).Anal.Calcd.for C 17 H 11 NO 3 S 2 : C, 59.81; H, 3.25; N, 4.10; S, 18.78%; Found: C, 59.72; H, 3.26; N, 4.01; S, 18.40.

[0057] Product 1 H NMR and FT-IR spectra are as Figure 5 with Image 6 Shown.

[0058] The ultraviolet-visible absorption spectra of the three thioxanthone dimethylformamide deriva...

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Abstract

The invention discloses a thioxanthone dicarboamide compound and a preparing method and application thereof. The structural formula of the thioxanthone dicarboamide compound is shown in the specification. The thioxanthone dicarboamide compound is used as a UV-LED photoinitiator for photopolymerization of a vinyl unsaturated resin system, and can be applied to the photocuring field, the photopolymerization field and the photocrosslinking field.

Description

Technical field [0001] The invention relates to the field of photopolymers, and mainly relates to a thioxanthone dimethylformamide compound and a preparation method and application thereof. Background technique [0002] UV-LED (UV Light Emitting Diodes) photopolymerization refers to a photopolymerization method that uses ultraviolet light emitting diodes as the energy output light source. Due to its advantages of low temperature, energy saving, low power consumption, long service life, single emission wavelength, etc., replacing the traditional high-pressure mercury lamp curing method has become the future development direction. It has been involved in traditional printing and coating fields such as coatings, adhesives, inks, printing plates, microelectronics, etc., and has further expanded to bone and tissue engineering biological materials, surface etching gratings, material surface modification, active / reactive Controlled polymerization and other fields, especially suitable f...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04C08F2/48C08F122/20
CPCC07D495/04C08F2/48C08F122/20
Inventor 何明辉崔艳艳
Owner 广州纽楷美新材料科技有限公司
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