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Novel hindered amine group-contained benzotriazole light stabilizer

A technology of benzotriazole and hindered amine, applied in the field of benzotriazole light stabilizer, can solve the problems of unsatisfactory ultraviolet absorption intensity and the like

Inactive Publication Date: 2012-03-28
DALIAN RES & DESIGN INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] This type of benzotriazole light stabilizer containing hindered amine groups is based on the benzene ring of alkyl-substituted phenols connected to the piperidinol structure, and its UV absorption strength is still often unsatisfactory

Method used

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  • Novel hindered amine group-contained benzotriazole light stabilizer
  • Novel hindered amine group-contained benzotriazole light stabilizer
  • Novel hindered amine group-contained benzotriazole light stabilizer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064]Add 10.0g (0.03195mol) 2-[2-hydroxy-4-ethoxycarbonylmethoxyphenyl]-2H-benzotriazole, 10.0 g (0.0637mol) 2,2,6,6-tetramethylpiperidinol, 0.2g dibutyltin oxide and 50mL xylene were reacted at 140°C for 6 hours. After the reaction was completed, the temperature was lowered, filtered, dried, and then recrystallized with ethyl acetate to obtain a white solid, namely 2-[2-hydroxyl-4-(2,2,6,6-tetramethylpiperidine-4-oxyl) Carbonylmethoxyphenyl]-2H-benzotriazole (compound II) 8.1g, yield 59.3%, high performance liquid chromatography (HPLC) purity 99.2%, melting point 160.8-161.0°C.

[0065] Elemental Analysis Results:

[0066]

Embodiment 2

[0068] Add 10.0 g (0.0288 mol) of 5-chloro-2-[2-hydroxy-4-ethoxycarbonylmethoxyphenyl]-2H-benzo Triazole, 10.0 g (0.0637 mol) of 2,2,6,6-tetramethylpiperidinol, 0.2 g of dibutyltin oxide and 50 mL of solvent oil were reacted at 140° C. for 7 hours. After the reaction was completed, the temperature was lowered, filtered, dried, and recrystallized from ethyl acetate to obtain a white solid, namely 5-chloro-2-[2-hydroxyl-4-(2,2,6,6-tetramethylpiperidine-4 -Oxy)carbonylmethoxyphenyl]-2H-benzotriazole (compound III) 7.7g, yield 57.8%, HPLC purity 99.1%, melting point 167.1-167.4°C.

[0069] Elemental Analysis Results:

[0070]

Embodiment 3

[0072] Add 10.0g (0.03195mol) 2-[2-hydroxy-4-ethoxycarbonylmethoxyphenyl]-2H-benzotriazole, 10.0 g (0.0585 mol) of 1,2,2,6,6-pentamethylpiperidinol, 0.2 g of tetrabutyl titanate and 50 mL of xylene were reacted at 140° C. for 6 hours. After the reaction was completed, the temperature was lowered, filtered, dried, and then recrystallized with ethyl acetate to obtain a white solid, namely 2-[2-hydroxyl-4-(1,2,2,6,6-pentamethylpiperidine-4-oxo yl)carbonylmethoxyphenyl]-2H-benzotriazole (compound IV) 7.8g, yield 55.4%, HPLC purity 99.3%, melting point 114.3-114.8°C.

[0073] Elemental Analysis Results:

[0074]

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Abstract

The invention relates to a hindered amine group-contained benzotriazole compound shown as a formula I, wherein common symbols are defined as those in claim 1. The invention further relates to a method for preparing the compound, and a use of the compound provided by the invention or the compound prepared according to the method provided by the invention as a light stabilizer. The light stabilizer can effectively stabilize thermosetting resins, thermoplastic resins, polyamide or polyester fibers, organic dyes, preparation of cellulose paper, paper for photographic film, ink, white or colored wax and the like and has very effective ultraviolet absorption activity and hindered amine light stability.

Description

[0001] This application is a divisional application of the application No. 200810167812.X entitled "Benzotriazole Light Stabilizer Containing Hindered Amine Group". technical field [0002] The invention relates to a benzotriazole light stabilizer containing hindered amine groups, belonging to the field of light stabilizers. Background technique [0003] Benzotriazole UV absorbers and hindered amine free radical scavengers are two types of light stabilizers commonly used in polymers. They can be used alone or in combination. After compounding, the application effect is better due to the synergistic effect . From the perspective of molecular design and atom economy, the design contains both benzotriazole and hindered amine structures in the same molecule, so that the research of compounds with two functions of ultraviolet absorption and free radical capture has more development potential. [0004] The reported structure of benzotriazole light stabilizer containing hindered a...

Claims

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Application Information

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IPC IPC(8): C07D401/12C07D401/14C08K5/3475C08K5/3492C09D11/00
Inventor 左洪亮邵玉昌张海涛
Owner DALIAN RES & DESIGN INST OF CHEM IND
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