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Benzotriazole-based (co)polymer, ultraviolet-absorbing paint containing same, and film coated with same

A technology of benzotriazole series and polymers, applied in the direction of radiation-absorbing coatings, coatings, chemical instruments and methods, etc., can solve the problems of insufficient ultraviolet shielding function, low absorption, difficult to use, etc., and achieve ultraviolet absorption performance Excellent effect with less coloring and excellent absorption performance

Active Publication Date: 2022-01-07
SHIN NAKAMURA CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the ultraviolet absorbers used so far have low absorption in the long-wavelength region of 350-400nm, especially 380-400nm, and the ultraviolet shielding function is insufficient
[0008] Patent Document 4 shows that by modifying benzotriazole derivatives with sesamol, light in the long-wavelength region can be efficiently absorbed, but the absorption of visible light in the short-wavelength region of 400 to 420 nm is strong. Adding this compound to the optical film or spectacle lenses, yellow coloring occurs, so it is difficult to use in the above-mentioned purposes

Method used

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  • Benzotriazole-based (co)polymer, ultraviolet-absorbing paint containing same, and film coated with same
  • Benzotriazole-based (co)polymer, ultraviolet-absorbing paint containing same, and film coated with same
  • Benzotriazole-based (co)polymer, ultraviolet-absorbing paint containing same, and film coated with same

Examples

Experimental program
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Embodiment

[0063] Hereinafter, the present invention will be described in more detail with examples and comparative examples of benzotriazole-based (co)polymers, coating materials and coating-coated films including these examples, but the present invention is not limited to these embodiments. In addition, "%" described in a synthesis example, an Example, and a comparative example shows "weight%", and "part" shows a "weight part."

[0064] [1. Synthesis of benzotriazole-based monomers]

Synthetic example 1

[0066] [Intermediate (a): Synthesis of 5-carboxy-2-(2-hydroxy-4-methoxyphenyl)-2H-benzotriazole]

[0067] [Chem 3]

[0068]

[0069] Install spherical condenser, thermometer, stirring device on the four-necked flask of 2000ml, add water 875ml, sodium carbonate 56.5g (0.533 mole), 178.8g (0.982 mole) of 4-amino-3-nitrobenzoic acid and make it dissolve, 197.1 g (1.028 mol) of 36% sodium nitrite aqueous solution was added. Install a spherical condenser, a thermometer, and a stirring device on a 3000ml four-necked flask, add 875ml of water, 372.0g (2.370 moles) of 62.5% sulfuric acid and mix them, cool to 3-7°C to obtain the product, and add the above-mentioned The product was stirred at the same temperature for 1 hour to obtain an aqueous diazonium salt solution. Install a spherical condenser, a thermometer, and a stirring device on a 5000ml four-necked flask, add 139.4g (1.009mol) of 1,3-dimethoxybenzene, 900ml of isopropanol, and 390ml of water and mix them, drop them at 5...

Synthetic example 2

[0073] [Intermediate (b): Synthesis of 5-carboxy-2-(2-hydroxy-4-methoxyphenyl)-2H-benzotriazole]

[0074] [chemical 4]

[0075]

[0076] Install a spherical condenser, a thermometer, and a stirring device on a 2000ml four-necked flask, add 107.1g (0.358 moles) of 5-carboxy-2-(2,4-dimethoxyphenyl)-2H-benzotriazole, 540ml of acetic acid, 365.2g (2.327 moles) of 62.5% sulfuric acid, and 221.8g (2.148 moles) of 95% sulfuric acid were stirred at 130-140°C for 20 hours, then 480ml of water was added, and the precipitate was filtered and washed with water to obtain crude crystals. The resulting crude crystals were reslurried and washed with 130 ml of isopropanol and 300 ml of 4-methyl-2-pentanone to obtain 5-carboxy-2-(2-hydroxyl-4-methoxyphenyl)-2H - Benzotriazole 59.5 g. The yield was 58% (calculated based on 5-carboxy-2-(2,4-dimethoxyphenyl)-2H-benzotriazole).

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Abstract

The present invention provides a kind of benzotriazole series (co) polymer that will comprise the raw material polymerization of the resorcinol type benzotriazole series monomer of following general formula, and this polymer is to reach the earth's surface from the sun The ultraviolet wavelength region of 300 to 400 nm, especially the wavelength region of 330 to 400 nm, where the accumulated energy is high, has excellent ultraviolet absorption performance and little coloration. [Preferred R 1 and R 2 for H, R 3 is an alkyl group, R 4 is H, alkyl, acryloxyalkyl or methacryloxyalkyl]

Description

technical field [0001] The present invention relates to a benzotriazole-based (co)polymer having ultraviolet absorbing properties and absorbing ultraviolet rays in a wide wavelength region, a paint containing the same, and a film coated with the paint. Background technique [0002] In the past, the absorption and shielding of ultraviolet rays, preventing the dissolution or leakage of ultraviolet absorbing components from the coating film, preventing the crystallization of ultraviolet absorbing components in the coating film, improving the weather resistance of the coating film, and improving the compatibility with other resins or compounding materials For the purpose of compatibility, a UV-absorbing (co)polymer was used. [0003] Mainly used are benzotriazole-based copolymers containing one or more alkanols having ultraviolet absorbing properties in a relatively short region centered around 300nm to 360nm A monomer composition obtained by copolymerizing a phenolic benzotria...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F20/36C09D5/32C09D179/04B32B27/00
CPCB32B27/00C08F20/36C09D5/32C09D179/04C09D139/04C08J7/04C08J5/18C08F26/06
Inventor 占野孝仁
Owner SHIN NAKAMURA CHEM CO LTD