Water-soluble polymerizable photosensitive monomer and its preparation method and application

A water-soluble, photosensitive technology, applied in the field of photocuring, can solve the problems of large molecular weight of photoinitiator, easy migration to the product surface, and high viscosity of prepolymer, so as to reduce migration and volatilization, improve photocuring efficiency and lubricity no drop effect

Active Publication Date: 2021-12-31
JIANGSU BIOSURF BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, most of the traditional light-curing system formulations are oil-soluble substances, which have inherent disadvantages: for example, the prepolymer has a high viscosity, and reactive diluent molecules (monomers) are used to adjust the viscosity of the system, but the degree to which monomers can reduce the viscosity of the system is limited. Some monomers are volatile and irritating, which will cause certain harm to the human body and the environment, and unreacted monomers will remain in the product after the light is over, and will easily migrate to the surface of the product during use and cause adverse effects
Domestic documents 2 and 3 disclose that benzophenone and thioxanthone photoinitiators are respectively introduced into the molecular chains of organosilicon macromolecules and polyethyleneimines to prepare water-soluble macromolecular photoinitiators. Macromolecular photoinitiators have good water solubility and can overcome the disadvantages of small molecule photoinitiators. However, the photoinitiator is introduced by grafting, and the proportion of photoinitiating units in the macromolecular chain is relatively small. It will affect the initiation efficiency of the photoinitiator; in addition, the molecular weight of the high molecular weight photoinitiator is too large, and the viscosity is too high so that it cannot be well dispersed, which will also affect its initiation activity
Domestic document 4 utilizes the reaction of alkaline substances and the carboxylic acid of the product itself to improve water solubility, and obtains a polymerizable and water-soluble photoinitiator, but it uses toxic triphenylphosphine as a reaction catalyst and the yield is not high. There are certain limitations in the application

Method used

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  • Water-soluble polymerizable photosensitive monomer and its preparation method and application
  • Water-soluble polymerizable photosensitive monomer and its preparation method and application
  • Water-soluble polymerizable photosensitive monomer and its preparation method and application

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no. 1 approach

[0048] The first embodiment of the present invention provides a water-soluble polymerizable photosensitive monomer.

[0049] The photosensitive monomer contains: 1) a unit containing a photosensitive structure; 2) a unit containing a quaternary ammonium salt structure; 3) a unit containing an unsaturated bond structure;

[0050] The unit containing the photosensitive structure is at least connected to the unit containing the quaternary ammonium salt structure through -C(=O)-, and the unit containing the unsaturated bond structure is at least connected to the unit containing the quaternary ammonium salt structure Units containing photosensitive structures are connected.

[0051] Preferably, the unit containing the photosensitive structure is directly connected to the unit containing the quaternary ammonium salt structure through -C(=O)-, and the unit containing the unsaturated bond structure is connected to the unit containing the quaternary ammonium salt structure through the ...

no. 2 approach

[0072] The second embodiment of the present invention provides a method for preparing a water-soluble polymerizable photosensitive monomer.

[0073] The water-soluble polymerizable photosensitive monomer of the present invention is obtained by carrying out acid halide treatment on the molecular end of the compound containing the photosensitive structure, and then reacting with (meth)acrylic esters containing tertiary amino groups.

[0074] Specifically, the following preparation process can be adopted:

[0075] 1) Dissolving the compound containing the photosensitive structure and the acid-binding agent in the organic solvent 1, slowly adding the halogenated alkyl acid halide solution dropwise therein, reacting in an ice bath for a period of time, then rising to room temperature to continue the reaction, and performing post-treatment after the reaction to obtain the compound containing Intermediates of photosensitive structures and halogens;

[0076]2) Dissolve the intermedia...

no. 3 approach

[0096] In the third embodiment of the present invention, the application of the water-soluble polymerizable photosensitive monomer of the present invention in the preparation of a hydrophilic lubricating coating is provided. Hydrophilic coatings of medical devices are generally prepared from photocurable components. The water-soluble polymerizable photosensitive monomer of the present invention can directly be used as a photoinitiator to promote the curing of the coating. Preferably, the water-soluble polymerizable Photosensitive monomers are used to copolymerize with other hydrophilic monomers to obtain photocurable polymers, and then the polymers are used in the preparation of hydrophilic coatings, so that the coating process does not require the addition of small molecule light Initiator, to obtain a hydrophilic coating with excellent lubricating properties and no odor. After repeated friction for 30 times in a simulated human tissue environment, the coating does not fall of...

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Abstract

The invention relates to a water-soluble polymerizable photosensitive monomer and its preparation method and application. The monomer comprises a unit containing a photosensitive structure, a unit containing a water-soluble quaternary ammonium salt structure, and a unit containing an unsaturated bond structure. The units of the structure are connected, and the unit containing the unsaturated bond structure is connected with the unit containing the photosensitive structure at least through the unit containing the water-soluble quaternary ammonium salt structure. The water-soluble polymerizable photosensitive monomer of the present invention has good compatibility in water-soluble curing systems, high photoinitiation efficiency, can reduce the migration and volatilization of photolytic fragments remaining in the system, and can effectively overcome the defect that small molecules are easy to migrate , and the water-soluble polymerizable photosensitive monomer of the present invention can prepare a hydrophilic coating with excellent lubricating properties.

Description

technical field [0001] The invention belongs to the field of photocuring technology, and in particular relates to a water-soluble polymerizable photosensitive monomer and its preparation method and application. Background technique [0002] Photocuring technology (UV) uses light to act on light-sensitive compounds to cause a series of photophysical and photochemical reactions to produce active substances, thereby triggering the polymerization and crosslinking of liquid oligomers (including monomers). It forms a solid product, which has the advantages of high efficiency and energy saving, and basically does not contain volatile solvents. It is known as "green technology" and has been widely used commercially. [0003] However, most of the traditional light-curing system formulations are oil-soluble substances, which have inherent disadvantages: for example, the prepolymer has a high viscosity, and reactive diluent molecules (monomers) are used to adjust the viscosity of the s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C227/18C07C229/12C09D139/06C08F226/10C08F220/36
CPCC09D139/06C07C229/12C08F226/10C08F220/36
Inventor 徐亚骏
Owner JIANGSU BIOSURF BIOTECH CO LTD
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