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Acrylate based hydroxyalkyl acid ester reactive diluent and preparation method and application thereof

A technology of hydroxyalkyl esters and reactive diluents, which is applied in the field of waste ultraviolet light curing, can solve problems such as hazards and complex processes, and achieve the effects of low equipment requirements, stable preparation process, and strong practicability

Inactive Publication Date: 2019-01-11
WUHAN OXIRAN SPECIALTY CHEM CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above two products have complicated processes and need to be purified by extraction, distillation, etc.
Chinese invention patent (application number: 200510031419.4 application date: 2005-04-05) discloses a kind of 1-hydroxyethyl acrylate, 4-hydroxychloropropyl maleate and its synthesis method as UV curable coating The reactive diluent has the characteristics of fast curing speed, no stimulation to the human body, low price, and film-forming properties; however, toxic epichlorohydrin is used as the raw material, and even a small amount of residue is harmful to the body

Method used

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  • Acrylate based hydroxyalkyl acid ester reactive diluent and preparation method and application thereof
  • Acrylate based hydroxyalkyl acid ester reactive diluent and preparation method and application thereof
  • Acrylate based hydroxyalkyl acid ester reactive diluent and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The preparation method of 1-hydroxyethyl acrylate, 4-hydroxyethyl maleate:

[0033] (1) Esterification reaction: Weigh 97g maleic anhydride solid, 116g hydroxyethyl acrylate respectively, then join the hydroxyethyl acrylate of 116g in the dry reactor, then add the quality that is esterification raw material (butadiene Acrylic anhydride and hydroxyethyl acrylate) 2.0% triethylamine and 0.3% p-hydroxyanisole, stir and heat up to 70°C, drop in 97g maleic anhydride solid in several times, keep warm at 75-85°C for 1 ~3h, until the acid value is in the range of 261~264mgKOH / g, the esterification reaction is considered to be completed.

[0034] (2) Alkoxylation reaction: add triphenylphosphine equivalent to 0.8% of the total mass of the target product in the esterified product obtained in step (1), and the reaction temperature is controlled at 80-90° C. Add a small amount of ethylene oxide, and then continue to add 44g of ethylene oxide to carry out alkoxylation reaction afte...

Embodiment 2

[0036] The preparation method of 1-hydroxypropyl acrylate group, 4-hydroxypropyl maleate:

[0037](1) Esterification reaction: Weigh 97g maleic anhydride solid, 130g hydroxypropyl acrylate respectively, then join the hydroxypropyl acrylate of 130g in the dry reactor, then add quality is esterification raw material (cis-butyl Acrylic anhydride and hydroxypropyl acrylate) 1.0% p-toluenesulfonic acid and 0.8% hydroquinone, stir and heat up to 75°C, drop 97g of maleic anhydride solid in several times, keep warm at 75-85°C for 1 ~3h, until the acid value is in the range of 245~250mg KOH / g, the esterification reaction is considered to be completed.

[0038] (2) Alkoxylation reaction: add triphenylphosphine equivalent to 0.5% of the total mass of the target product in the esterified product obtained in step (1), and control the reaction temperature at 75 to 85° C. Add a small amount of propylene oxide, and then continue to add 60g of propylene oxide to carry out the alkoxylation rea...

Embodiment 3

[0040] The preparation method of 1-hydroxyethyl methacrylate, 4-hydroxypropyl phthalate:

[0041] (1) Esterification reaction: Weigh 148g of phthalic anhydride solids and 132.6g of hydroxyethyl methacrylate respectively, then add 132.6g of hydroxyethyl methacrylate into the dry reactor, and then add a mass of Esterification raw materials (phthalic anhydride and hydroxyethyl methacrylate) 1.0% triphenylphosphine and 1.0% p-tert-butylcatechol, stirred and heated to 70 °C, and 148g phthalate For acid anhydride solids, keep warm at 80-90°C for 1-3 hours until the acid value is within the range of 200-204 mgKOH / g, the esterification reaction is considered to be completed.

[0042] (2) Alkoxylation reaction: add urotropine equivalent to 1.0% of the total mass of the target product in the esterified product obtained in step (1), and the reaction temperature is controlled at 70-80° C. Add a small amount of propylene oxide, and then continue to add 61g of propylene oxide to carry out ...

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Abstract

The invention discloses an acrylate based hydroxyalkyl acid ester reactive diluent and a preparation method and an application thereof. The preparation method of the acrylate based hydroxyalkyl acid ester reactive diluent comprises an esterification reaction and an alkoxylation reaction. The preparation method specifically comprises the following steps: carrying out the esterification reaction onanhydride and a raw material containing hydroxyl acrylate; and then carrying out the alkoxylation reaction with ethylene oxide and propylene oxide to prepare a target product. The acrylate based hydroxyalkyl acid ester reactive diluent provided by the invention is a novel green compound, is used as a novel UV curing coating reactive diluent, is free of halogen, non-toxic and non-irritant, high incuring speed, high in practicality and superior to a common acrylate monomer in aspects, and is stable in preparation process, mild in reaction condition, simple to operate, free of post treatment steps, free of three waste discharge and green and environment-friendly.

Description

technical field [0001] The invention relates to the field of waste ultraviolet light curing, in particular to an acrylate-based hydroxyalkyl ester reactive diluent, a preparation method and application thereof. Background technique [0002] Ultraviolet light curing material (hereinafter referred to as UV curing material) is a research hotspot in recent years. It has the characteristics of low cost, fast curing speed, high efficiency, no volatile solvent, little pollution and low energy consumption. It is widely used in coatings, Adhesives, printing inks and other fields. Reactive diluent is an important component of UV curable coatings, accounting for about 40-60% of the product formula. Reactive diluent is a substance containing polymerizable functional groups, which can not only dilute the resin, adjust the viscosity of the system, but also participate in photosensitive The polymerization reaction has an important influence on the photocuring speed and cured film performa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/26C07C69/80C07C69/60C09D163/10
CPCC07C67/08C07C67/26C09D163/10C07C69/80C07C69/60
Inventor 王艳张静任凡付远波王亮
Owner WUHAN OXIRAN SPECIALTY CHEM CO
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