Water-soluble thiaxanthon-polyether visible light initiator and preparing method and application thereof

A thioxanthone, water-soluble technology, applied in the field of water-soluble thioxanthone-polyether visible light initiator and preparation, can solve the disadvantageous advantages of macromolecular initiators, complex synthesis methods, hindering photoactive groups, etc. problem, to achieve the effect of improving the light initiation efficiency, strong penetrating ability, and high initiation efficiency

Active Publication Date: 2016-05-25
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional ultraviolet photoinitiator thioxanthone (isopropylthioxanthone, US Patent6025408) widely used commercially has poor compatibility with the photocuring system and requires the joint action of additives, which is easy to produce odor, toxicity, and migration. , yellowing and other issues
Chinese patent CN1546488A discloses a preparation method of thioxanthone containing co-initiator amino groups, but the photoactive group on the main chain is easily hindered by macromolecular chain segments, which is not conducive to exerting the advantages of macromolecular initiators ; Chinese patent CN1594399A discloses a method for preparing a copolymerized thioxanthone photoinitiator, but its synthetic method is complicated
Chinese patent CN102120783 discloses a preparation method of thioxanthone photoinitiators containing aliphatic tertiary amino groups, but these small molecule photoinitiators cannot be used in the visible light region

Method used

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  • Water-soluble thiaxanthon-polyether visible light initiator and preparing method and application thereof
  • Water-soluble thiaxanthon-polyether visible light initiator and preparing method and application thereof
  • Water-soluble thiaxanthon-polyether visible light initiator and preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] (1) Preparation of thioxanthone:

[0035] In a 250mL single-necked round bottom flask, add 11.35g (0.05mol) of N-(4-bromophenyl)-N-methylacetamide, 7.70g (0.05mol) of thiosalicylic acid, 0.95g of copper powder, iodine Cuprous chloride 1.00g, anhydrous sodium carbonate 10.60g (0.10mol), N,N-dimethylformamide 100mL, heated to 100°C for 10h under stirring, cooled, filtered, the filtrate was concentrated, washed with water, and filtered. The filtrate was acidified with dilute hydrochloric acid to precipitate a white precipitate, filtered, and dried; weighed 9.03g into a 500mL single-necked flask, then added 500g of polyphosphoric acid (PPA), heated to 130°C and stirred for 5h, then heated the The reaction solution was poured into a beaker containing 700mL of ice water, cooled, and a yellow solid was precipitated, filtered, and the filter cake was washed with KHCO 3 The aqueous solution was washed, dried, and recrystallized in ethyl acetate: petroleum ether = 1:1 to obtain ...

Embodiment 2

[0045] (1) preparation of thioxanthone

[0046] Add N-(4-bromo-2-methylphenyl)-N-isopropylacetamide 13.45g (0.05mol) and thiosalicylic acid 7.70g (0.05mol) in a 250mL single-necked round bottom flask, Copper powder 0.95g, cuprous iodide 1.00g, anhydrous potassium carbonate 13.8g (0.10mol), N,N-dimethylacetamide 100mL, stirred at 160°C for 15h, cooled, filtered, the filtrate was concentrated, washed with water, filter. The filtrate was acidified with dilute hydrochloric acid to precipitate a white precipitate, filtered, and dried; weigh 10.29g into a 500ml one-necked flask, add 100mL of concentrated sulfuric acid under stirring, stir at room temperature for 1h, heat up to 60°C, react at 60°C for 2h, cool, Slowly added to 1L of boiling water; cooled to room temperature, filtered, the filter cake was washed with saturated NaOH aqueous solution, washed with water, dried, and subjected to silica gel column chromatography to obtain yellow 3-methyl-2-isopropylaminothioxanthone 6.98 ...

Embodiment 3

[0056] (1) preparation of thioxanthone

[0057] Add 16.25 g (0.05 mol) of N-(4-bromo-2-ethylphenyl)-N-hexylacetamide, 7.70 g (0.05 mol) of thiosalicylic acid, and copper powder into a 250 mL single-necked round bottom flask 0.95g, cuprous iodide 1.00g, sodium hydroxide 4.0g (0.10mol), N,N-dimethylformamide 100mL, stirred and heated to reflux for 18h, cooled, filtered, the filtrate was concentrated, washed with water, filtered. The filtrate was acidified with dilute hydrochloric acid to precipitate a white precipitate, filtered, and dried; weighed 11.97g into a 500ml single-necked flask, added 100mL of concentrated sulfuric acid under stirring, stirred at room temperature for 1h, raised the temperature to 80°C, reacted at 80°C for 10h, cooled, Slowly added to 1L of boiling water; cooled to room temperature, filtered, the filter cake was washed with saturated KOH aqueous solution, washed with water, dried, and subjected to silica gel column chromatography to obtain 9.26 g of yel...

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Abstract

The invention relates to a water-soluble thiaxanthon-polyether visible light initiator and a preparing method and application thereof. Thioether is obtained from 4-bromaniline and derivatives of 4-bromaniline through nucleophilic substitution, aromatic amine is introduced into a thiaxanthon structure through concentrated acid dehydration cyclization, then chloromethyl is introduced onto a photoinitiator through nucleophilic substitution, and the thiaxanthon visible light initiator containing a polyether chain segment is formed through nucleophilic substitution. Due to the introduction of polyether, the water solubility of the product is high, various raw materials can be provided for the polymer due to various choices of polyether molecular weight, and then the structure and solubility of the polymer are flexible and changeable. The light initiator can be applied to visible light polymerization of unsaturated active materials. Due to the fact that the light initiator is a macromolecule light initiator and free of toxin, micromolecule additives are not needed, toxic micromolecule fragments are not generated during initiation or after initiation, and the light initiator can be used for preparing food-grade products.

Description

technical field [0001] The invention relates to the field of photoinitiators, in particular to a water-soluble thioxanthone-polyether visible light initiator, a preparation method and application. Background technique [0002] Photopolymerization is a very important technology that is widely used in many fields, such as photocurable coatings, adhesives, inks, microelectronics, photoresists, etc. In these applications, the key process of controlling photopolymerization is photoinitiation. The photoinitiator absorbs light energy under the irradiation of light, and generates active species by itself or by interacting with co-initiators to initiate monomer polymerization, which affects the photocuring rate. play a decisive role. The absorption wavelength of the traditional photoinitiating system is generally less than 400nm, and it is mainly used in UV curing systems. The photoinitiating system developed in the early stage, such as organic peroxide, can modify its molecular st...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/48C07D335/16C08F2/48C08F120/56C08F120/28C08F126/10
CPCC07D335/16C08F2/48C08F120/28C08F120/56C08F126/10C08G65/48
Inventor 唐红定武青青熊英
Owner WUHAN UNIV
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