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Antifouling aid and application thereof in ultraviolet photocureable coatings

A light-curing coating and light-curing technology, used in antifouling/underwater coatings, biocide-containing paints, polyurea/polyurethane coatings, etc. It can achieve excellent hydrophobic and oleophobic and anti-fouling effects, improve hydrophobic and oleophobic performance, and lasting anti-fouling effect.

Active Publication Date: 2017-11-10
SHANGHAI CHENGYING NEW MATERIALS +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, fluorine-containing compounds have the disadvantage of high cost, so an organic silicon compound with low price and low surface energy is used to cooperate with fluorine-containing compounds to reduce surface tension, improve hydrophobic and oleophobic effect, and achieve anti-fouling function. is arousing people's general attention
[0004] Chinese patent CN103665022A discloses an antifouling additive of perfluoropolyether alkoxysilane, but the additive is synthesized using a two-step synthesis method. The first step uses flammable solvent ether, and expensive perfluoropolyether acyl Fluorine reacts with allylamine to obtain allyl perfluoropolyetheramide, and the synthesis time is relatively long, and the second step of reaction needs to be removed before the solvent is removed.
The second step reaction adopts dichloromethane, a relatively toxic low-boiling solvent, and requires a more expensive platinum catalyst. The above-mentioned product allyl perfluoropolyether amide is used to react with trimethoxysilane. The reaction time is long, and it needs to be removed. solvent
However, both fluorine-containing hyperbranched polymers and siloxane oligomers need to be prepared separately, while the former requires desolvation and vacuum drying steps, which is complicated to operate
Siloxane oligomers are prepared by hydrolysis of methacryloxypropyl triethoxysilane in ethanol solution under acidic conditions. Although the preparation process is simple, it is not easy to obtain oligomers with expected molecular weights. If Improper operation will cause crosslinking
In addition, the fluorine-containing hyperbranched polymer mentioned in this invention is only a multifunctional random binary copolymer with double bonds in the side chain, and its fluorine content is relatively low, because its fluorine raw material is only 2 -(perfluorohexyl) ethyl acrylate, the fluorine-containing chain segment is short, so the hydrophobic and oleophobic effect is low, and the polymer does not have the structural regularity of the hyperbranched polymer, so the viscosity is high, which will cause the coating The poor compatibility of other components in the system will affect the coating effect

Method used

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  • Antifouling aid and application thereof in ultraviolet photocureable coatings
  • Antifouling aid and application thereof in ultraviolet photocureable coatings
  • Antifouling aid and application thereof in ultraviolet photocureable coatings

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Into a 250ml four-necked flask equipped with magnetic stirring, serpentine condenser, thermometer and water separator, under the protection of nitrogen, add 30 grams of toluene and 68 grams of two-terminal carboxyl modified silicone oil (molecular weight 4000, 0.017mol) , 2.42 g glycidyl methacrylate (0.017 mol), 0.07 g benzyl triethylammonium bromide, 0.14 g p-hydroxyanisole, and react for 3 hours at 100 degrees. Then, 2.86 g of hexamethylene diisocyanate (0.017 mol) and 0.01 g of dibutyltin dilaurate were added and reacted at 80 degrees for 2 hours. Then add 20 g of toluene, 1.97 g of hydroxyethyl acrylate (0.017 mol), and 0.14 g of p-hydroxyanisole, and react at 80 degrees for 2 hours. Add 20 grams of toluene, 23.45 grams of maleic acid half ester of perfluoroalkyl ethanol (acid value 94.9mgKOH / g, 0.040mol), 5.40 grams of hyperbranched polyester polyol (hydroxyl value 592.2mgKOH / g, 0.057mol-OH) ), 0.28 g of p-hydroxyanisole, 0.27 g of methanesulfonic acid, reflux for...

Embodiment 2

[0040] Into a 250ml four-necked flask equipped with magnetic stirring, snake condenser, thermometer and water separator, under the protection of nitrogen, add 30 grams of toluene and 75 grams of two-terminal carboxyl modified silicone oil (molecular weight 5000, 0.015mol) , 2.13 g glycidyl methacrylate (0.015 mol), 0.077 g benzyl triethylammonium bromide, 0.15 g p-hydroxyanisole, and react for 3 hours at 100 degrees. Then 2.52 g of hexamethylene diisocyanate (0.015 mol) and 0.01 g of dibutyltin dilaurate were added, and the reaction was carried out at 80 degrees for 2 hours. Then add 20 g of toluene, 1.74 g of hydroxyethyl acrylate (0.015 mol), and 0.15 g of p-hydroxyanisole, and react at 80 degrees for 2 hours. Add 20 grams of toluene, 20.69 grams of maleic acid half ester of perfluoroalkyl ethanol (acid value 94.9mgKOH / g, 0.035mol), 4.74 grams of hyperbranched polyester polyol (hydroxyl value 592.2mgKOH / g, 0.05mol-OH) ), 0.31 g of p-hydroxyanisole, 0.24 g of methanesulfonic ...

Embodiment 3

[0042] Into a 250ml four-necked flask equipped with magnetic stirring, snake condenser, thermometer and water separator, under the protection of nitrogen, add 30 grams of toluene and 78 grams of two-terminal carboxyl modified silicone oil (molecular weight 6000, 0.013mol) , 1.85 g of glycidyl methacrylate (0.013 mol), 0.080 g of benzyl triethylammonium bromide, 0.16 g of p-hydroxyanisole, and react for 3 hours at 100 degrees. Then, 2.19 g of hexamethylene diisocyanate (0.013 mol) and 0.01 g of dibutyltin dilaurate were added and reacted at 80 degrees for 2 hours. Then add 20 g of toluene, 1.51 g of hydroxyethyl acrylate (0.013 mol), and 0.16 g of p-hydroxyanisole, and react at 80 degrees for 2 hours. Add 20 grams of toluene, 17.93 grams of maleic acid half ester of perfluoroalkyl ethanol (acid value 94.9mgKOH / g, 0.030mol), 4.11 grams of hyperbranched polyester polyol (hydroxyl value 592.2mgKOH / g, 0.043mol-OH) ), 0.32 g of p-hydroxyanisole, 0.21 g of methanesulfonic acid, reflu...

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Abstract

The invention discloses an antifouling aid and application thereof in ultraviolet photocureable coatings; the antifouling aid is fluorine-silicon light-curable hyperbranched polyester with the following structure containing acrylate and maleic acid ester structures as shown in the specification, and under UV irradiation, double bonds of the acrylate and maleic acid ester of the structure of the antifouling aid can be crosslinked with double bonds of acrylic resin and acrylate monomers in coatings for curing to form coating layers with excellent hydrophobic and oleophobic performances, so that the excellent anti fouling effect can be achieved.

Description

Technical field [0001] The invention belongs to the technical field of ultraviolet light curing antifouling materials, and specifically relates to a preparation method of a fluorosilicone photocurable hyperbranched polyester containing acrylate and maleate structures and its use as an antifouling adjuvant in ultraviolet curing coatings. application. Background technique [0002] Ultraviolet curing coatings (UV coatings) have been widely used in mobile phones, tablet computers, etc. due to their high efficiency, energy saving, environmental protection, and economic advantages, as well as their excellent scratch resistance, chemical resistance, and high gloss. The surface of the plastic substrate of electronic products such as optical lenses, machine control panels, GPS panels, etc. is hardened to improve the hardness, transparency, wear resistance, and impact resistance of the plastic substrate. However, during the use of these electronic products, fingerprints, skin oils, ink st...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00C08G77/38C08G77/388C09D5/16C09D175/14
Inventor 虞明东王艳梅党东风
Owner SHANGHAI CHENGYING NEW MATERIALS
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