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Silicon-containing double-curing group resin and preparation method thereof

A dual-curing, resin technology, applied in the direction of application, coating, ink, etc., can solve the problems of not easy to dry, poor adhesion, uneven partial curing, etc.

Inactive Publication Date: 2013-11-27
SHENZHEN POLYTECHNIC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The free radical photocuring system has the advantages of fast curing speed and various types of initiators, but there are also problems such as not easy surface drying, large shrinkage of polymerization volume, poor adhesion, and no post-curing effect. At present, UV-curable products mainly use free radicals. curing system
The cationic photocuring system has the advantages of small volume shrinkage, strong adhesion, and post-curing, but it also has the disadvantages of slow curing speed, less types of oligomers and reactive diluents, etc. It is mainly used in dark coatings or ink systems
In order to give full play to the advantages of various curing methods and avoid their shortcomings, the research on various hybrid UV curing systems has been paid more and more attention, and various forms of hybrid UV curing systems have been developed, mainly UV-free Radical-cation hybrid curing, UV radical-thermal hybrid curing, UV-air hybrid curing, UV-moisture hybrid curing, etc. These hybrid curing systems are mainly composed of two or more resins containing different curing groups. However, there are relatively few reports on the synthesis of resins with two curing groups at the same time.
[0004] In various hybrid UV curing systems, most researchers use the mixture of several resins with different curing groups, so there are problems such as uneven local curing or poor compatibility between resins.
[0005] Resins commonly used in ultraviolet (UV) curing products include epoxy acrylate, urethane acrylate, polyester acrylate, etc. These resins can meet the needs of most applications, but in order to make the cured film have some special properties to meet For special needs, groups containing fluorine, phosphorus, silicon and other elements can be introduced into oligomers, monofunctional or multifunctional diluents. The introduction of fluorine-containing monomers is mainly to improve the surface properties of the cured film, but its price is relatively high. High, which affects its use; the synthesis and use of phosphorus-containing monomers are mainly designed for flame-retardant requirements, and there are not many units engaged in research in this area; silicon-containing compounds have low viscosity-temperature coefficients and low prices. , excellent interface properties, good softness, good lubricity, chemical stability and outstanding weather resistance, etc., have been widely concerned and researched

Method used

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  • Silicon-containing double-curing group resin and preparation method thereof
  • Silicon-containing double-curing group resin and preparation method thereof
  • Silicon-containing double-curing group resin and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] In the first step, add 520g of bisphenol A epoxy (epoxy E51) into a 1000mL three-necked flask, heat the oil bath to 100°C, stir, and add acrylic acid (the molar ratio of epoxy group to acrylic acid is 2:1) Add a total mass of 0.2% catalyst N,N-dimethylbenzylamine (BDMA) and 0.3% polymerization inhibitor p-hydroxyanisole, and drop them into the epoxy resin. After 5 hours of reaction, the acid value of the system is less than 3mgKOH / g, epoxy monoacrylate Second step, in the there-necked flask of 1000mL, add the toluene diisocyanate (TDI) of 0.5mol, be heated to 60 ℃, dibutyltin dilaurate joins the hydroxyl silicone oil containing 0.5mol hydroxyl by 0.2% of gross mass ( Hydroxyl content 6%), add dropwise into toluene diisocyanate (TDI) solution, continue to react for 2.5h after dropping, add 0.2% p-hydroxyanisole to 0.25mol hydroxyethyl acrylate, add the above reaction system, heat up React at 100°C for 2 hours to obtain polyurethane acrylate with -NCO group at one end ...

Embodiment 2

[0042] In the first step, add 250g of bisphenol A epoxy (epoxy E44) into a 500mL three-necked flask, heat the oil bath to 110°C, stir, and add acrylic acid (the molar ratio of epoxy group to acrylic acid is 2:1) Add a total mass of 0.4% catalyst triethylbenzyl ammonium chloride and 0.3% polymerization inhibitor hydroquinone, add dropwise to the epoxy resin, and react for 4.5 hours. The acid value of the system is less than 3mgKOH / g, that is, the epoxy Monoacrylate In the second step, add 1mol of diphenylmethane diisocyanate (MDI) in a three-necked flask of 1000mL, heat to 60°C, dibutyltin dilaurate is added to the hydroxyl silicone oil containing 1mol of hydroxyl by 0.3% of the total mass (hydroxyl content 9%), add dropwise into diphenylmethane diisocyanate (MDI) solution, continue to react for 2.5h after dropping, add 0.3% p-hydroxyanisole to 0.5mol hydroxyethyl methacrylate, Add the above reaction system, raise the temperature to 100°C and react for 2.5 hours to obtain pol...

Embodiment 3

[0044] In the first step, add 600g of tetrabromobisphenol A epoxy resin into a 1000mL three-necked flask, heat the oil bath to 90°C, stir, and then add it to the metered acrylic acid (the molar ratio of epoxy group to acrylic acid is 2:1) The total mass of 0.5% catalyst tris(acetylacetonate) complex iron (Ⅲ) and 0.5% polymerization inhibitor p-hydroxyanisole are added dropwise to the epoxy resin. After 6 hours of reaction, the acid value of the system is less than 3mgKOH / g, that is, the epoxy Monoacrylate ; In the second step, add 1mol of hexamethylene diisocyanate (HDI) in a 1000mL three-necked flask, heat to 80°C, and add dibutyltin dilaurate to the hydroxyl silicone oil containing 1mol of hydroxyl by 0.2% of the total mass (hydroxyl content 3.5%), add dropwise into hexamethylene diisocyanate (HDI) solution, continue to react for 2.5h after dropping, add 0.5% p-hydroxyanisole to 0.5mol hydroxypropyl acrylate, add the above In the reaction system, heat up to 90°C and react ...

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Abstract

The invention discloses silicon-containing double-curing group resin and a preparation method thereof. Two preparation methods can be applied in the invention. The first preparation method comprises the following steps of: synthesizing acrylic epoxy monoester firstly; reacting hydroxyl silicone oil, diisocyanate and hydroxyl acrylic resin to obtain urethane acrylate with an NCO functional group at one end; and reacting two kinds of resin together to obtain silicon-containing urethane acrylate-modified epoxy monoester; and the second preparation method comprises the following steps of: synthesizing the acrylic epoxy monoester firstly; reacting dihydric alcohol, the diisocyanate and the hydroxyl acrylic resin to obtain the urethane acrylate with the NCO functional group at one end; reacting two kinds of resin together and then reacting the mixture with amino silicone oil to obtain the silicon-containing double-curing group resin. According to the invention, groups with two different curing modes are contained in the same resin molecule and the problem of compatibility of resin in different resin compounding, mixing and curing systems is solved; and on the other hand, a urethane acrylate-modified flexible chain and an organic silicon chain segment are modified so as to improve the performance of the resin.

Description

technical field [0001] The invention relates to the technical field of organic polymer synthesis; in particular, it relates to an organic silicon chain segment, and has both ultraviolet light-induced free radical curing groups (acrylate double bonds) and ultraviolet light-induced cationic curing groups or thermal curing groups. The invention discloses a preparation method of group (epoxy group) resin, which can be used in the fields of free radical-cation ultraviolet light mixed curing type or free radical light curing-thermal mixed curing type coating, adhesive, ink and the like. Background technique [0002] Ultraviolet (UV) curing technology has developed rapidly because of its characteristics of fast, solvent-free, and suitable for assembly line production. It can be used as a surface protective coating for plastics, metals, wood, paper, optical fibers, etc., and is widely used in industry. UV curing system is generally composed of photoactive oligomers (resins), monofu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G18/67C08G18/61C08G59/17C08G18/83C08G81/00C09D175/16C09D187/00C09J175/16C09J187/00C09D11/10C09D11/00
Inventor 刘红波林峰张武英徐玲
Owner SHENZHEN POLYTECHNIC
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