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Triazine light stabilizer containing hindered amine groups

A light stabilizer, hindered amine technology, applied in the field of light stabilizers, can solve the problem of no obvious improvement in absorption intensity

Inactive Publication Date: 2011-04-13
DALIAN RES & DESIGN INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of triazine light stabilizer containing hindered amine groups has achieved relatively satisfactory results through simple light stability tests, but compared with general commercial triazine UV absorbers, the UV absorption intensity has not been significantly improved, and its Photostability still needs to be further improved

Method used

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  • Triazine light stabilizer containing hindered amine groups
  • Triazine light stabilizer containing hindered amine groups
  • Triazine light stabilizer containing hindered amine groups

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028]Add 10.0 g (0.0183 mol) 2-phenyl-4,6-di(2-hydroxy-4-ethoxycarbonylmethoxyphenyl)- 1,3,5-triazine, 9g (0.0573mol) 2,2,6,6-tetramethylpiperidinol, 0.3g dibutyltin oxide and 50mL xylene were reacted at 140°C for 8h. After the reaction was completed, the temperature was lowered, filtered, dried, and recrystallized from N,N-dimethylformamide to obtain a yellow solid, namely 2-phenyl-4,6-bis[2-hydroxyl-4-(2,2,6 , 6-tetramethylpiperidine-4-oxyl)carbonylmethoxyphenyl]-1,3,5-triazine (II) 9.1g, yield 64.7%, high performance liquid chromatography (HPLC) purity 98.7 %, melting point 114.0-115.3°C, MS molecular ion peak 767.5.

[0029] Elemental Analysis Results:

[0030]

Embodiment 2

[0032] Add 10.0 g (0.0183 mol) 2-phenyl-4,6-di(2-hydroxy-4-ethoxycarbonylmethoxyphenyl)- 1,3,5-triazine, 10g (0.0585mol) 1,2,2,6,6-pentamethylpiperidinol, 0.3g dibutyltin oxide and 50mL xylene were reacted at 140°C for 8h. After the reaction was completed, the temperature was lowered, filtered, dried, and then recrystallized with N,N-dimethylformamide to obtain a yellow solid, that is, 2-phenyl-4,6-bis[2-hydroxyl-4-(1,2,2 , 6,6-tetramethylpiperidine-4-oxyl)carbonylmethoxyphenyl]-1,3,5-triazine (III) 8.7g, yield 59.6%, high performance liquid chromatography (HPLC) The purity is 98.1%, the melting point is 202.3-203.2°C, and the MS molecular ion peak is 795.5.

[0033] Elemental Analysis Results:

[0034]

Embodiment 3

[0036] Add 10.0 g (0.0183 mol) 2-phenyl-4,6-di(2-hydroxy-4-ethoxycarbonylmethoxyphenyl)- 1,3,5-Triazine, 11g (0.0457mol) N-hexyl-2,2,6,6-pentamethylpiperidinol, 0.2g tetrabutyl titanate and 30mL chlorobenzene were reacted at 120°C for 8h. After the reaction was completed, the temperature was lowered, filtered, dried, and recrystallized from N,N-dimethylformamide to obtain a yellow solid, namely 2-phenyl-4,6-bis[2-hydroxyl-4-(1-hexyl-2 , 2,6,6-tetramethylpiperidine-4-oxyl)carbonylmethoxyphenyl]-1,3,5-triazine (IV) 9.1g, yield 53.1%, HPLC ( HPLC) purity 98.2%, melting point 195.3-196.2°C, MS molecular ion peak 935.5.

[0037] Elemental Analysis Results:

[0038]

[0039]

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Abstract

The invention relates to a triazine compound which is as shown in general formula I and contains hindered amine groups, wherein general symbols are as defined in claim 1. The invention further relates to a method for preparing the compound and an application of the light stabilizer. The triazine compound containing the hindered amine groups can effectively stabilize thermosetting resin, thermoplastic resin, polyamide or polyester fiber, organic dyes, cellulose paper preparations, paper for photographic films, printing ink, white or colored wax and the like, and has the advantages of very effective ultraviolet absorption activity and hindered amine light stability.

Description

technical field [0001] The compound involved in the invention is a triazine light stabilizer containing a hindered amine group and belongs to the field of light stabilizers. Background technique [0002] Triazine 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 triazine 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. [0003] The structural formula of the reported triazine light stabilizer containing hindered amine group is as follows: [0004] [0005] where R 3 Contains a hindered amine group. For example, the hindered amine structure is directly introduced...

Claims

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Application Information

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IPC IPC(8): C08K5/3492C07D401/14C08L23/12C08L69/00C08L33/08C08L23/06C08L27/06C08L25/06C08L25/16C08L67/02C08L77/00C08L79/08C08L59/00C08L33/20C08L71/00C08L73/00C08L81/06C08L71/12C08L61/06C08L61/24C08L67/08C08L75/02C08L75/00C08L63/00C08L83/04C08L61/32C08L7/00C08L21/00C08L55/02C08L25/12C08L25/14C08L1/02C08L33/00D21H17/07C09D11/00C08L91/06
Inventor 张宇邵玉昌刘威
Owner DALIAN RES & DESIGN INST OF CHEM IND
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