Carbonyl-containing modified heterocyclic amine, preparation method and application in multifunctional acrylic ester thereof

A carbonyl polycyclic amine and acrylate technology, which is applied in the synthesis field of carbonyl-modified polycyclic amines, can solve the problems of easy amine migration, small dosage, high odor, etc., and achieves reduction of curing shrinkage and high product purity. , the effect of improving catalytic activity

Active Publication Date: 2015-11-11
GUANGDONG BOSSIN NOVEL MATERIALS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[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 effect of oxygen inhibition, thereby increasing the UV curing rate and contributing to the complete curing of deep and surface layers; however, most of the existing active amines are small molecular amines, such as diethylamine, dipropylamine, di-n-butylamine, etc. Through the Michael addition reaction, the tertiary amination of part of the double bond of the polyfunctional monomer is obtained, such as TMPTA or TPGDA modified active amine, but this type of active amine still has disadvantages such as strong odor, easy amine migration and serious yellowing , should not be used in large quantities in the UV system, and can only be used as an externally added co-initiator; Low-viscosity resin with tertiary amine co-initiator active groups to overcome the problems of small amount of active amine co-initiator in the UV system, strong odor, easy amine migration and serious yellowing in the prior art

Method used

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  • Carbonyl-containing modified heterocyclic amine, preparation method and application in multifunctional acrylic ester thereof
  • Carbonyl-containing modified heterocyclic amine, preparation method and application in multifunctional acrylic ester thereof
  • Carbonyl-containing modified heterocyclic amine, preparation method and application in multifunctional acrylic ester thereof

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0044] Synthetic Example 1 A kind of carbonyl-containing bicyclic polyamine 1

[0045]

[0046] Add 177.2g of diethyl carbonate and 258.4g of anhydrous piperazine into a three-necked flask equipped with a rectification device, a thermometer and a stirrer; after stirring evenly, gradually raise the temperature to 80°C, react at a constant temperature for 6 hours, and control the temperature of the rectification port at At about 60-70°C, after almost no distillate is separated, the temperature is raised to 90-100°C to remove low-boiling point by-products and impurities by vacuum distillation to obtain 350.2 g of a transparent and colorless product (actual yield 95.5%).

Synthetic example 2

[0047] Synthetic example 2 a kind of carbonyl-containing polycyclic oligomeric polyamine 2

[0048]

[0049] Add 162.0g of dimethyl carbonate and 194.6g of anhydrous piperazine into a three-necked flask equipped with a rectification device, a thermometer and a stirrer; after stirring evenly, gradually raise the temperature to 80°C, and react at a constant temperature for 12 hours, and the temperature of the rectification port is controlled at At about 60-70°C, after almost no distillate is separated, the temperature is raised to 90-100°C to remove low-boiling point by-products and impurities by vacuum distillation, and 290.2g of a transparent and colorless product is obtained (actual yield 95.9%).

Synthetic example 3

[0050] Synthetic example 3 a kind of carbonyl-containing bicyclic polyamine 3

[0051]

[0052] Add 97.0g of ethylene carbonate and 374.7g of isophoronediamine into a three-necked flask equipped with a rectification device, a thermometer and a stirrer; after stirring evenly, gradually raise the temperature to 80°C for 6 hours, and control the temperature of the rectification port at 60°C At ~70°C, after almost no distillate was separated, the temperature was raised to 90-100°C to remove low-boiling point by-products and impurities by vacuum distillation to obtain 385.2 g of a transparent and colorless product (actual yield 95.5%).

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Abstract

The invention relates to carbonyl-containing modified heterocyclic amine, a preparation method and application in multifunctional acrylic ester thereof. The carbonyl-containing modified heterocyclic amine is heterocyclic amine containing at least two ring structures, and is formed through carrying out ammonolysis reaction on carbonic ester and cycloaliphatic diamine, wherein the cycloaliphatic diamine is one or more selected from piperazine, isophorone diamine, 1, 4-hexamethylenediamine, 1-methyl-2, 4-diaminocyclohexane, N, N'-dimethyl-1 and 2-diaminocyclohexane. According to the application, when the carbonyl-containing modified heterocyclic amine is applied to multifunctional acrylic ester, the curing velocity of multifunctional acrylic ester is remarkably increased, the cure shrinkage rate of multifunctional acrylic ester is decreased, and the hardness and high temperature resistance of multifunctional acrylic ester are remarkably improved; and besides, the generated carbonyl-containing modified heterocyclic amine multifunctional acrylic ester has the characteristics of being light in smell, and small in amine mobility and less prone to yellowing.

Description

technical field [0001] The present invention relates to the synthesis of carbonyl-containing modified polycyclic amines, in particular to a carbonyl-containing modified polycyclic amine and its preparation method and its application in multifunctional acrylates, in particular to carbonyl-containing modified polycyclic amines in multifunctional Applications in acrylate monomers and (branched) polyether acrylates. 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 effect of oxygen inhibition, thereby increasing the UV curing rate and contributing to the complete curing of deep and surface layers; however, most of the existing active amines are small molecular amines, such as diethylamine, dipropylamine, di-n-bu...

Claims

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Application Information

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IPC IPC(8): C07D295/215C07C273/18C07C275/18C12P7/62
CPCC07C273/1809C07C273/1863C07C275/18C07D295/215C12P7/62
Inventor 庞来兴李志云巫朝剑汪慧曾贤健
Owner GUANGDONG BOSSIN NOVEL MATERIALS TECH CO LTD
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