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Perfluoro alkyl phosphoester acrylic ester and preparation thereof

A technology of perfluoroalkyl phosphate acrylate and monohydroxy acrylate, which is applied in the field of UV-curable hydrophobic and oleophobic materials, which can solve the problems of difficult to obtain polymer films, no hydrophobic and oleophobic properties, and limited applications

Inactive Publication Date: 2008-11-12
JIANGSU LITIAN TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Switzerland "Progress in Organic Coatings" (Progress in Organic Coatings, 2002, 45: 359-363) reported that perfluoroalkyl acrylates were used as additives in UV-cured wood protective coatings to improve the hydrophobicity of wood surfaces. It is oily and improves its resistance to acids, alkalis, and organic solvents, but this technology only focuses on its hydrophobic and oleophobic properties, and does not involve flame retardancy
The U.S. "Journal of Applied Polymer Science" (Journal of Applied Polymer Science, 2005, 97: 185-194) reported the preparation of phosphate acrylate, and studied its photocuring kinetics and flame retardancy after curing. The effects of different additions in commercial resins on the flame retardant performance were compared, but this technology only studied the flame retardant performance, and did not introduce the concept of hydrophobic and oleophobic properties
The Swiss "Journal of Fluorine Chemistry" (Journal of Fluorine Chemistry) reported a series of preparation methods for fluorine-containing phosphates during 2000--2005, including (Journal of Fluorine Chemistry, 2003, 121: 23-31) reported perfluorinated The preparation of alkyl phosphate monoacrylate and monomethacrylate, and the corresponding polymers were obtained by general free radical polymerization, and the hydrophobic, oleophobic and flame retardant properties of the polymers were studied. Functional group monomers, it is difficult to directly obtain polymer films by UV irradiation, which limits its application in the field of UV curing

Method used

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  • Perfluoro alkyl phosphoester acrylic ester and preparation thereof
  • Perfluoro alkyl phosphoester acrylic ester and preparation thereof
  • Perfluoro alkyl phosphoester acrylic ester and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Under ice-water bath conditions, add 15.3g phosphorus oxychloride and 400mL ether to a three-necked flask reactor equipped with a condensation and stirring device, then add the ether solution containing 46.4g perfluorooctyl alcohol and 10.1g triethylamine to Slowly drop into the reactor at a rate of one drop per second, return to room temperature and stir for 8 hours after the dropwise addition; then add the ether solution containing 11.6g of hydroxyethyl acrylate and 10.1g of triethylamine into the above reaction mixture to continue the reaction for 24 hours, Then add 4.5g of butanediol and 10.1g of triethylamine in ether solution, stir at room temperature until the infrared phosphorus oxychloride absorption peak disappears; the reaction product is filtered, neutralized, washed with saturated sodium bicarbonate solution and distilled water successively, and separated , and the solvent was removed to obtain a light yellow solid, that is, perfluorooctyl phosphate acrylate...

Embodiment 2

[0038] Under ice-water bath conditions, add 15.3g of phosphorus oxychloride and 100mL ether to a three-necked flask reactor equipped with a condensation and stirring device, and then add the ether solution containing 10.0g of trifluoroethanol and 7.9g of pyridine at a rate of one drop per second Slowly add dropwise into the reactor, return to room temperature and stir for 8 hours after the dropwise addition; then add the ether solution containing 11.6g hydroxyethyl acrylate and 7.9g pyridine to the above reaction mixture and continue to react for 24 hours, then add 5.9g hexadiene Alcohol and 7.9g of pyridine ether solution, stirred at room temperature until the infrared phosphorus oxychloride absorption peak disappears; the reaction product is filtered, neutralized, washed with saturated sodium bicarbonate solution and distilled water successively, separated, and the solvent is removed to obtain light yellow The solid was trifluoroethyl phosphate acrylate monomer, and the yield...

Embodiment 3

[0042]Under ice-water bath conditions, add 15.3g phosphorus oxychloride and 400mL ether to the three-neck flask reactor equipped with condensation and stirring device, then add the ether solution containing 46.4g perfluorooctyl alcohol and 7.9g pyridine at a rate of Slowly add one drop into the reactor, return to room temperature and stir for 8 hours after the addition is complete; then slowly add the ether solution containing 20.8g of 1,5-pentanediol and 15.8g of pyridine into the above reaction mixture dropwise, and continue to react at room temperature to The absorption peak of the infrared phosphorus oxychloride group disappeared, then 15.8g of pyridine was added and cooled in an ice-water bath, and an ether solution containing 19.0g of acryloyl chloride was slowly added dropwise. After the dropwise addition, the reaction was continued at room temperature for 12 hours. The reaction product was filtered, neutralized, washed successively with saturated sodium bicarbonate solu...

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Abstract

The invention discloses perfluoroalkyl group phosphate ester acrylic ester and a method for making the same. The method comprises the following steps that: firstly, a fluoro-alcohol compound is reacted with phosphorus oxychloride and then is reacted with dibastic alcohol so as to synthesize perfluoroalkyl group phosphate ester; then, the acrylated treatment of the perfluoroalkyl group phosphate ester is carried out, or the perfluoroalkyl group phosphate ester is directly added in dibastic alcohol containing acrylic acid double bond so as to obtain perfluoroalkyl group radical which is connected with acrylic ester radical through phosphate ester bond; moreover, a molecular end contains perfluoroalkyl group phosphate ester of two acrylic ester double bonds. The method has cheap and easily obtained raw materials and simple operation, and is convenient for industrialized production; the obtained perfluoroalkyl group phosphate ester acrylic ester can be quickly solidified through adopting ultraviolet light irradiation; moreover, the obtained coating has excellent hydrophobicity and lipophobicity and high fire retardation efficiency, thereby having a broad industrial application prospect.

Description

technical field [0001] The invention belongs to the technical field of ultraviolet curing hydrophobic and oleophobic materials, and in particular relates to perfluoroalkyl phosphate acrylate and a preparation method thereof. Background technique [0002] Acrylic resins have been widely used in the field of UV curing since the late 1960s when German Bayer first successfully developed UV-curable wood coatings. Acrylate has been widely used in adhesives, inks, coatings, composite materials, etc. due to its characteristics of no solvent volatilization, fast speed, and low energy consumption during light curing. Fluorine-containing materials have polyfluoroalkyl groups (referred to as R f group), the surface tension of the material is very low, and it has good hydrophobicity and oleophobicity, and is widely used in the surface treatment of fabrics, leather, paper, etc. Organophosphorus flame retardants are an important new type of low-smoke and halogen-free systems, mainly incl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/10C09D4/02C09D5/16
Inventor 缪慧张丽丽
Owner JIANGSU LITIAN TECH
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