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Water-soluble fluorine-containing macromolecule photoinitiator, and preparation method and application thereof

A water-soluble fluorine-containing, photoinitiator technology, applied in the field of water-soluble fluorine-containing macromolecular photoinitiators and its preparation, can solve environmental and human hazards, easy migration and volatilization of photolytic fragments, and restrict the application of photocuring systems, etc. problems to achieve harm reduction

Active Publication Date: 2014-08-20
邳州市博睿投资管理有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional small-molecule free radical photopolymerization initiators and photolytic fragments remaining in the system are easy to migrate and volatilize, causing aging and yellowing of cured materials, odor and toxicity, which restricts the application of photocurable systems in food and pharmaceutical packaging, etc.
In addition, there are still many shortcomings in the traditional photopolymerization system, such as the volatility of the reactive diluent, which is harmful to the environment and human body, etc.

Method used

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  • Water-soluble fluorine-containing macromolecule photoinitiator, and preparation method and application thereof
  • Water-soluble fluorine-containing macromolecule photoinitiator, and preparation method and application thereof
  • Water-soluble fluorine-containing macromolecule photoinitiator, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] A water-soluble fluorine-containing macromolecular photoinitiator, the structural formula is as follows:

[0011]

[0012] (1) Add 3 mol of 3,4,5-trihydroxybenzophenone (THK) and 4.2 mol of acryloyl chloride as raw materials into 100 mL of dichloromethane, then add 4.2 mol of triethylamine as a catalyst, and Reaction in the bath for 12h, after the reaction, wash twice with dilute hydrochloric acid with a solute mass fraction of 20%, wash twice with saturated sodium hydroxide, then wash three times with deionized water, dry over anhydrous magnesium sulfate, and obtain the product containing THK of C=C, 4-acryloyloxy-3,5-dihydroxy-benzophenone;

[0013] (2) 1 mol of anhydrous potassium carbonate, 1 mol of 4-acryloyloxy-3,5-dihydroxy-benzophenone, and 1 mol of 3-chloro-2 hydroxypropyl sodium sulfonate were dissolved in 100 mL of N , N-dimethylformamide, then add 0.5% PEG-1000 of three kinds of raw materials as a phase transfer catalyst, stir, the temperature is control...

Embodiment 2

[0018] A water-soluble fluorine-containing macromolecular photoinitiator, the structural formula is as follows:

[0019]

[0020] (1) Add 3 mol of 3,4,5-trihydroxybenzophenone (THK) and 3.6 mol of acryloyl chloride as raw materials into 100 mL of dichloromethane, then add 3.6 mol of triethylamine as a catalyst, ice Reaction in the bath for 12h, after the reaction, wash twice with dilute hydrochloric acid with a solute mass fraction of 20%, wash twice with saturated sodium hydroxide, then wash three times with deionized water, dry over anhydrous magnesium sulfate, and obtain the product containing THK of C=C, 4-acryloyloxy-3,5-dihydroxy-benzophenone;

[0021] (2) 1 mol of anhydrous potassium carbonate, 1 mol of 4-acryloyloxy-3,5-dihydroxy-benzophenone, and 1 mol of 3-chloro-2 hydroxypropyl sodium sulfonate were dissolved in 100 mL of N , N-dimethylformamide, then add 1% PEG-1000 of three kinds of raw materials as a phase transfer catalyst, stir, the temperature is controlle...

Embodiment 3

[0026] A water-soluble fluorine-containing macromolecular photoinitiator, the structural formula is as follows:

[0027]

[0028] (1) Add 3 mol of 3,4,5-trihydroxybenzophenone (THK) and 4.5 mol of acryloyl chloride as raw materials into 100 mL of dichloromethane, then add 4.5 mol of triethylamine as a catalyst, and Reaction in the bath for 24h, after the reaction, wash twice with dilute hydrochloric acid with a solute mass fraction of 20%, wash twice with saturated sodium hydroxide, then wash three times with deionized water, dry over anhydrous magnesium sulfate, and obtain the product containing THK of C=C, 4-acryloyloxy-3,5-dihydroxy-benzophenone;

[0029] (2) 1 mol of anhydrous potassium carbonate, 1 mol of 4-acryloyloxy-3,5-dihydroxy-benzophenone, and 1 mol of 3-chloro-2 hydroxypropyl sodium sulfonate were dissolved in 100 mL of N , N-dimethylformamide, then add 1.5% 18-crown 6 ether with the quality of three raw materials as a phase transfer catalyst, stir, control th...

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Abstract

The invention discloses a water-soluble fluorine-containing macromolecule photoinitiator, and a preparation method and application thereof. Fluorine-containing micromolecules and a water-soluble photoinitiator are subjected to copolymerization reaction to obtain the water-soluble fluorine-containing macromolecule photoinitiator. The water-soluble fluorine-containing macromolecule photoinitiator overcomes the defect of high volatility in the traditional micromolecule photoinitiator especially in the infrared drying process of water-based paint and the defect of high tendency to yellowing; the water system has certain solubility, and thus, can initiate photopolymerization of the water-soluble system, thereby greatly reducing the hazards on the environment and human body; the fluorine-containing macromolecule photoinitiator is endowed with certain migration capacity due to the surface tension and surface energy of the fluorine atoms, and thus, can spontaneously migrate to the external surface of the system when being in the water system so as to finally form concentration gradient distribution in the water-based system, thereby initiating gradient polymerization; and part of the water-soluble fluorine-containing macromolecule photoinitiator migrating to the surface can form an oxygen isolation layer, and thus, has certain anti-oxygen and polymerization inhibition effects.

Description

technical field [0001] The invention belongs to the field of polymer material synthesis. Specifically, the invention relates to a water-soluble fluorine-containing macromolecular photoinitiator and its preparation method and application. Background technique [0002] As an environment-friendly coating, light-curing coatings have developed vigorously in recent years. In 1946, Inmot Company of the United States obtained the first patent on ultraviolet (UV) curing. In 1967, Bayer Company of Germany industrialized UV curing technology, which led to the concept of initiator. Any active intermediate substance that absorbs radiation energy, undergoes chemical changes, and has the ability to initiate polymerization is a photoinitiator. In 1970, Ciba-Geigy invented I-651, which laid the foundation for the rapid development of photoinitiators, and also established Ciba-Geigy’s leading position in the field of photoinitiator research and production. [0003] Photoinitiator is one of...

Claims

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Application Information

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IPC IPC(8): C08F2/48C08F220/22C08F220/38C08F120/14
Inventor 王克敏
Owner 邳州市博睿投资管理有限公司
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