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Silicon-containing ultraviolet absorber, and preparation method of polyurethane copolymer thereof

A technology of UV absorbers and copolymers, which is applied in the field of preparation of silicon-containing UV absorbers and their polyurethane copolymers. It can solve problems such as single functionality, unsatisfactory requirements, and single functionality, so as to achieve difficult phase separation and enhanced stability. Sexuality, the effect of prolonging the storage time

Pending Publication Date: 2019-10-22
大连振邦氟涂料股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the main functions of the UV absorbers currently on the market and reported in the literature are very single, and basically only have the function of UV absorption.
In modern people's emphasis on multi-functional applications for materials and raw materials, a single function is obviously unable to meet the needs
[0004] Most of the UV absorbers and copolymer materials are combined by physical blending. Although the physical blending operation is simple, the UV absorbers prepared by this method are prone to phase separation from the copolymer materials, so there are certain limitations.

Method used

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  • Silicon-containing ultraviolet absorber, and preparation method of polyurethane copolymer thereof
  • Silicon-containing ultraviolet absorber, and preparation method of polyurethane copolymer thereof
  • Silicon-containing ultraviolet absorber, and preparation method of polyurethane copolymer thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] (1) The preparation method of silicon-containing ultraviolet absorber:

[0030] Mix 0.5mmol of 4-methylphenyl(2,4,6-trihydroxy-3(3-hydroxy-3-methylbutyl)phenyl)methanone and 3mmol of diisopropylethylamine and add 5mL of water 1,2-dichloroethane and 0.2 mmol di-tert-butyltin dichloride. After stirring evenly, react at 50°C for 15 minutes and cool to room temperature, then slowly add 0.8 mmol triisopropylsilyloxymethane chloride dropwise, and continue stirring for 1.5 hours. Then it was quenched with 1 mL of methanol, diluted with 0.5 mL of dichloromethane, and extracted twice with 10 mL of 0.03 mol / L sodium bicarbonate solution and water. The organic layers were combined, dried with Na2SO4 for 12 h, filtered and concentrated to remove the reaction solvent to obtain a silicon-containing ultraviolet absorber.

[0031] (2) The preparation method of polyurethane copolymer:

[0032] After adding 0.5mmol polypropylene glycol in the reactor, add dropwise 0.1mmol isophorone d...

Embodiment 2

[0034] (1) The preparation method of silicon-containing ultraviolet absorber:

[0035] Mix 2mmol of 4-ethylphenyl (2,4,6-trihydroxy-3(3-hydroxy-3-methylbutyl)phenyl)methanone and 10mmol of diisopropylethylamine and add 7mL of water 1,3-dichloropropane and 0.5 mmol di-tert-butyltin dichloride. After stirring evenly, react at 60° C. for 30 minutes, then cool to room temperature, then slowly add 1.2 mmol of triisomethylsiloxymethane chloride dropwise, and continue stirring for 3 hours. Then, it was quenched with 3 mL of methanol, diluted with 1.3 mL of dichloromethane, and extracted twice with 50 mL of 0.05 mol / L sodium bicarbonate solution and water. The organic layers were combined, dried with Na2SO4 for 15 h, filtered and concentrated to remove the reaction solvent to obtain a silicon-containing ultraviolet absorber.

[0036] (2) The preparation method of polyurethane copolymer:

[0037] After adding 9mmol polyethylene glycol in the reactor, 2.3mmol toluene diisocyanate and...

Embodiment 3

[0039] (1) The preparation method of silicon-containing ultraviolet absorber:

[0040] Mix 8mmol of 4-propylphenyl (2,4,6-trihydroxy-3(3-hydroxy-3-methylbutyl)phenyl)methanone and 26mmol of diisopropylethylamine and add 12mL of Water 1-chlorobutane and 3.6 mmol di-tert-butyltin dichloride. After stirring evenly, react at 65° C. for 45 minutes and cool to room temperature, then slowly add 2.7 mmol triisoethylsiloxymethane chloride dropwise, and continue stirring for 5 hours. Then, it was quenched with 6 mL of methanol, diluted with 4.8 mL of dichloromethane, and extracted three times with 120 mL of 0.08 mol / L sodium bicarbonate solution and water. The organic layers were combined, dried with Na2SO4 for 20 h, filtered and then concentrated to remove the reaction solvent to obtain a silicon-containing ultraviolet absorber.

[0041] (2) The preparation method of polyurethane copolymer:

[0042] After adding 13.5mmol of polytetrahydrofuran diol in the reactor, 14.5mmol of hexame...

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Abstract

The invention discloses a preparation method of a silicon-containing ultraviolet absorber, and a preparation method of a polyurethane copolymer of the silicon-containing ultraviolet absorber. The silicon-containing ultraviolet absorber is represented by a formula shown in the description; and in the formula, R1 is a C1-C3 alkyl group, and R2, R3 and R4 are C1-C3 alkyl groups or aromatic groups. The silicon-containing ultraviolet absorber is synthesized from 4-substituted phenyl(2,4,6-trihydroxy-3(3-hydroxy-3-methylbutyl)phenyl)methanone and its derivatives and (triisopropylsiloxy)methyl chloride and its derivatives. The polyurethane copolymer is prepared from a polyol, a diisocyanate, and the synthesized silicon-containing ultraviolet absorber by an internal emulsification process. The silicon-containing ultraviolet absorber prepared in the invention has an ultraviolet absorbing function, the active group hydroxyl group contained in the ultraviolet absorber can be bonded to a polyurethane molecular chain, and the silicon element can effectively increase the functionality of the polymer.

Description

technical field [0001] The invention belongs to the field of ultraviolet absorbers and polymer materials, in particular to the preparation of a silicon-containing ultraviolet absorber and its polyurethane copolymer. Background technique [0002] The wavelength bands of ultraviolet rays reaching the ground after passing through the clouds are mainly 280-400nm UVA and UVB. They have extremely high energy, about 300-400kJ / mol, and are the main external cause of aging of polymer materials. The mechanism of UV-induced aging and degradation of polymer materials is that its energy can cause free radicals in the molecular chain of the polymer to break, resulting in a decline in physical and mechanical properties and yellowing of the color. This phenomenon is more serious as the UV exposure time increases. Therefore, the development and application of ultraviolet absorbers is the most common and convenient method for anti-aging and anti-fading of polymer materials. [0003] At pre...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18C08G18/66C08G18/48C08G18/32C08G18/38C08G18/34C08G18/42
CPCC07F7/1804C07F7/1892C08G18/3893C08G18/4238C08G18/4825C08G18/4833C08G18/4854C08G18/664C08G18/6659C08G18/6674C08G18/6692
Inventor 刘洪珠翁舒婷展雪胡俊平王瑞东
Owner 大连振邦氟涂料股份有限公司
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