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Ultraviolet absorbing coating materil and film coated with said coating material

A polymerizable monomer, benzotriazole-based technology, used in radiation-absorbing coatings, coatings, layered products, etc., can solve the problems of low light resistance, no light resistance, and reduced light absorption capacity, and achieve absorption The effect of excellent performance, excellent UV absorption performance and UV shielding performance, excellent absorption performance and excellent UV shielding performance

Active Publication Date: 2019-12-06
SHIN NAKAMURA CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these compounds generally have low light resistance, deteriorate due to exposure to sunlight, and reduce light absorption ability, so they cannot be used for a long time
In addition, there is no description of light resistance in Patent Documents 4 to 5
[0009] The sesamol-type benzotriazole-based copolymer of Patent Document 3, which is generally known to have high light resistance, can absorb light in the short-wavelength region of ultraviolet light and visible light, but its absorption is weak above 420 nm, and there are ultraviolet light in the vicinity of 300 to 330 nm. The problem of weak absorption

Method used

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  • Ultraviolet absorbing coating materil and film coated with said coating material
  • Ultraviolet absorbing coating materil and film coated with said coating material
  • Ultraviolet absorbing coating materil and film coated with said coating material

Examples

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Embodiment

[0065] 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."

[0066] [1. Synthesis of benzotriazole-based monomers]

Synthetic example 1

[0068] [Compound (a): 2-(3-tert-butyl-2-hydroxy-5-methoxyphenyl)-2H-benzotriazole-5-carboxylic acid-2-methacryloyloxyethyl ester Synthesis][Chemical 3]

[0069]

[0070] Install a spherical condenser, a thermometer, and a stirring device on a 200ml four-necked flask, add 100ml of water, 6.5g (0.061mol) of sodium carbonate, and 20.0g (0.110mol) of 4-amino-3-nitrobenzoic acid to dissolve, add 22.7 g (0.118 mol) of 36% sodium nitrite aqueous solution. Install a spherical condenser, a thermometer, and a stirring device on a 500ml four-necked flask, add 100ml of water, 43.0g (0.274 moles) of 62.5% sulfuric acid and mix, cool to 3-7°C to obtain the product, and add the above-mentioned The product was stirred at the same temperature for 2 hours to obtain an aqueous diazonium salt solution. Install a spherical condenser, a thermometer, and a stirring device on a 1000ml four-necked flask, add 18.0g (0.100 moles) of 2-tert-butyl-4-methoxyphenol, 10ml of isopropanol, and 140ml of wa...

Synthetic example 2

[0091] [Compound (b): Synthesis of 2-(2-hydroxy-5-methoxyphenyl)-2H-benzotriazole-5-carboxylic acid-2-methacryloyloxyethyl ester] [Chem. 4 ]

[0092]

[0093] Except changing 2-tert-butyl-4-methoxyphenol into 4-methoxyphenol, the compound (b ). The melting point is 94°C, the maximum absorption wavelength λmax is 309.8nm and 373.2nm, and the molar absorptivity ε of these wavelengths are 14700 and 13100, respectively.

[0094] In addition, the purity of compound (b) was determined by HPLC analysis.

[0095]

[0096] Device: L-2130 (manufactured by Hitachi High-Technologies Co., Ltd.)

[0097] Column used: Inertsil ODS-3 4.6×150mm 5 μm

[0098] Column temperature: 25°C

[0099] Mobile phase: acetonitrile / water=9 / 1 (phosphoric acid 3ml / L)

[0100] Flow rate: 1.0ml / min

[0101] Detection: UV250nm

[0102]

[0103] HPLC peak area percentage purity 93.4%

[0104] In addition, as a result of NMR measurement of the compound (b), a result supporting the above-mentioned str...

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Abstract

Provided is a benzotriazole (co)polymer which is obtained by polymerizing a starting material that contains a methoquinone-type benzotriazole monomer represented by the general formula, and which hasabsorption in a wide ultraviolet wavelength region of 300-400 nm, while absorbing light in a short-wavelength visible light region up to around 450 nm. (In the formula, R1 represents a hydrogen atom or an alkyl group; R2 represent an alkyl group; and R3 represents an acryloyloxy alkyl group or a methacryloyloxy alkyl group.)

Description

technical field [0001] The present invention relates to a benzotriazole-based (co)polymer having ultraviolet absorbing properties and absorbing ultraviolet light in a wide wavelength region and light in a short visible light 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 compo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F20/36B32B27/00C09D5/32C09D133/14
CPCB32B27/00C08F20/36C09D5/32C09D133/14
Inventor 占野孝仁
Owner SHIN NAKAMURA CHEM CO LTD
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