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A kind of polycyclic amine modified (branched) polyether acrylate and preparation method thereof

A polyether acrylate and branched polyether technology, used in inks, additive processing, household appliances, etc., can solve the problems of low mechanical strength of cured films, large curing shrinkage, application and promotion restrictions, etc., and reduce amine migration. The effect of high stability, small curing shrinkage, and simple product purification

Active Publication Date: 2017-05-03
南京玖泰新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are more mature ones such as methoxanone (MK) series and 44'-diphenoxybenzophenone (DPBP). Compared with BP, the maximum absorption wavelength of benzophenone derivatives has a certain degree The red shift phenomenon, the photoinitiated polymerization efficiency is higher, especially when it is compatible with BP or active amine, the photoinitiated efficiency is greatly improved, but due to the defects such as high toxicity and easy yellowing, some are even identified as carcinogens, making it The application and promotion are limited; therefore, the development of a benzophenone-derived photoinitiation system with good comprehensive performance has become a bottleneck in the development of this technology
[0004] Polyether acrylate has the characteristics of low viscosity, low shrinkage and low price, which is very in line with the urgent demand for materials in industries such as UV inkjet and 3D printing; Poor cohesion, low mechanical strength of the cured film, large curing shrinkage, and slow curing speed, etc., which are also technical problems that need to be solved urgently

Method used

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  • A kind of polycyclic amine modified (branched) polyether acrylate and preparation method thereof
  • A kind of polycyclic amine modified (branched) polyether acrylate and preparation method thereof
  • A kind of polycyclic amine modified (branched) polyether acrylate and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0049] Synthesis Example 1 Polyether Acrylate 1 (Mn≈862, functionality 3)

[0050] A kind of polyether triacrylate and preparation method thereof, comprises following two steps:

[0051] a. Transesterification reaction: Take 400g polyether triol (Mn≈700, Dow VOANOL 2070), 343.2g ethyl acrylate, 1.2g trinonylphenyl phosphite, 0.2g 2,6-di-tert-butyl Base-4-methylphenol, after uniform dispersion, add 5g of immobilized enzyme Novozyme 435 and 0.1g of lanthanum dodecylsulfonate, stir and react at 40°C for 24h;

[0052] b. Purification treatment: After filtering the mixture obtained in the previous step, the filtrate was subjected to vacuum rotary evaporation, and the ethanol and excess methacrylic acid generated by the reaction were removed to obtain 490.2 g of transparent and colorless esterified product (solid content 99.2%, viscosity 85 mPa ·s / 25℃, the esterification rate (based on polyether polyol as the base substrate, the same below) is 97.4%).

Synthetic example 2

[0053] Synthesis Example 2 Branched Polyether Acrylate 2 (Mn≈1022, Functionality 9)

[0054] A kind of branched polyether acrylate and preparation method thereof, concrete steps are as follows:

[0055] (1) Synthesis of branched polyether polyols

[0056] Glycerol is used as raw material to form branched polyether polyols (Mn≈536, functionality 9, branching degree 0.72) through one-step condensation under acidic conditions;

[0057] (2) Enzyme-catalyzed transesterification reaction, including the following two steps:

[0058] a. Transesterification reaction: take 300g of the above-mentioned branched polyether polyol, 550.0g methyl acrylate, 1.8g trinonylphenyl phosphite, 0.25g p-hydroxyanisole, after dispersing evenly, add 8g of curing enzyme Novozyme 435 and 0.1g lanthanum dodecylsulfonate, stirred and reacted at 50°C for 24h; the chemical reaction formula is as follows

[0059]

[0060] b. Purification treatment: After filtering the mixture obtained in the previous ste...

Synthetic example 3

[0061] Synthesis Example 3 Polyether Acrylate 3 (Mn≈1162, functionality 3)

[0062] A kind of polyether triacrylate and preparation method thereof, comprises following two steps:

[0063] a. Transesterification reaction: Take 400g polyether triol (Mn≈1000, VOANOL CP-1055), 384.4g methyl acrylate, 3.2g trinonylphenyl phosphite, 0.4g p-hydroxyanisole, and disperse After uniformity, add 6g immobilized enzyme LVK-F100 and 0.1g lanthanum methanesulfonate, and stir and react at 40°C for 24h;

[0064] a. Purification treatment: After filtering the mixture obtained in the previous step, the filtrate was subjected to vacuum rotary evaporation, and the methanol and excess methyl acrylate generated by the reaction were removed to obtain 463.0 g of transparent and colorless esterified product (solid content 99.5%, viscosity 105 mPa· s / 25℃, the esterification rate is 97.1%).

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Abstract

The invention relates to polycyclic amine modified (branched) polyether acrylate and a preparation method and application thereof. The polycyclic amine modified (branched) polyether acrylate is prepared by taking heteropolycyclic amine with diphenyl ketone and polycyclic tertiary amide structure as a modifier for Michael addition reaction and introducing the polycyclic tertiary amide structure into part of double bonds of (branched) polyether acrylate. The polycyclic amine modified (branched) polyether acrylate is low in viscosity and curing shrinkage rate and high in curing speed, overcomes the defect that conventional active amine is large in smell, prone to amide migration and yellowing and is a photocuring material having great prospect.

Description

technical field [0001] The invention relates to the technical field of radiation curable materials, in particular to a polycyclic amine modified (branched) polyether acrylate and its preparation method and application. Background technique [0002] It is well known that aliphatic tertiary amines can be used as co-initiators to form composite initiators with hydrogen-abstracting photoinitiators benzophenone (BP) or heterocyclic aromatic ketones to synergistically promote the production of active free radicals and Effectively reduce the oxygen inhibition effect, thereby increasing the UV curing rate, and contribute to the complete curing of the deep layer and the surface layer. However, most of the existing active amines are small molecular amines, such as diethylamine, dipropylamine, di-n-butylamine, etc., which are obtained by tertiary amination of part of the double bonds of polyfunctional monomers through Michael addition reaction, such as TMPTA or Active amine modified b...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/48C09D11/30B33Y70/00
Inventor 庞来兴李志云巫朝剑汪慧曾贤健
Owner 南京玖泰新材料科技有限公司
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