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Hindered amine compound and preparation method thereof

A technology for hindered amines and compounds, applied in the field of hindered amine compounds and their preparation, can solve the problems of accelerated photooxidative degradation of materials and the like

Inactive Publication Date: 2012-12-19
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

However, GW-944 is easily soluble in organic solvents such as dimethyl carbonate. When it is used as a light stabilizer for sealing materi

Method used

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  • Hindered amine compound and preparation method thereof
  • Hindered amine compound and preparation method thereof
  • Hindered amine compound and preparation method thereof

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[0027] The present invention also provides a preparation method for the aforementioned hindered amine compound, comprising the following steps: A) reacting the compound of formula (II) with a protective reagent in a protective atmosphere to obtain an amino-protected intermediate product; B) adding the amino The protected intermediate product is reacted with the terminal alkene compound of the formula (III), and the hindered amine compound of the formula (I) is obtained after deprotection. The protective atmosphere is a protective atmosphere well known to those skilled in the art, preferably nitrogen.

[0028]

[0029] Wherein, m=1~9, n=3~10, X is Cl, Br or I. m is preferably 1-6, more preferably 2-4.

[0030] The compound of the formula (II) is a light stabilizer known to those skilled in the art as GW-944.

[0031] In step A, the molar ratio of the compound of the formula (II) to the protecting reagent is 1:2~2.5, preferably 1:2~2.2. The reaction time of the reaction is...

Embodiment 1

[0049] The preparation of embodiment 1 GW-944

[0050] 1.1 Cool down 120ml of toluene in an ice bath to below 10°C, add 40g of cyanuric chloride, stir, slowly add 50ml of toluene solution dissolved in 27.52g of tert-octylamine dropwise, after 2 hours of reaction, dropwise add 20% cyanuric chloride 50ml of NaOH aqueous solution was reacted for 2h, allowed to stand, and the organic phase was separated and washed with 10% NaOH aqueous solution to obtain an organic phase containing intermediate product IV.

[0051] 1.2 Add the organic phase containing 0.2 mol of intermediate product IV obtained in 1.1, 0.2 mol of hexamethylenediamine piperidine and 50 ml of NaOH aqueous solution with a mass concentration of 20% into a 500 ml autoclave, replace the air in the autoclave with nitrogen three times, and fill with nitrogen To a pressure of 2MPa, heat to 60°C, stir for 4 hours, heat up to 180°C, react for 6 hours, cool down, filter, wash the organic phase with 10% NaOH aqueous solution, ...

Embodiment 2

[0057] Under the condition of nitrogen protection, mix and stir 0.2 mol of GW-944 obtained in 1.2, 0.4 mol of di-tert-butyl dicarbonate, 0.18 mol of potassium carbonate and 120 ml of dichloromethane. After 4 hours of reaction, add 0.3 mol of allyl bromide , Continue to react for 10h. Add dilute hydrochloric acid to adjust the pH value of the reaction solution to 5.0, remove the solvent under reduced pressure, extract with ether, anhydrous Na 2 SO 4 After drying and purification by n-hexane / ethyl acetate column chromatography, the hindered amine compound with the structure of formula (I) was obtained, and its average relative molecular mass was 2960.

[0058] The hindered amine compounds of the formula (I) structure obtained in Example 2 were analyzed by nuclear magnetic resonance to obtain their hydrogen spectrum and carbon spectrum. The results are as follows:

[0059] 1 HNMR (CDCl 3 ,ppm): 5.87(-C=CH), 5.19(-C=CH), 3.73(-CH 2 ), 3.49 (-CH 2 ),2.63(-CH),2.44(-CH),2.26(-...

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Abstract

The invention discloses a hindered amine compound and a preparation method of the hindered amine compound. The structural formula of the hindered amine compound is shown as formula (I). The preparation method comprises the steps of: carrying out reaction of the compound shown as formula (II) with a protective reagent in a protective atmosphere to obtain an amino protective intermediate; and further carrying out reaction with an end alkene compound shown as formula (III), and de-protecting to obtain the hindered amine compound shown as the formula (I). Compared with the prior art GW-994, amino on GW-994 piperidine rings is protected by protective groups, and the end alkene groups are guided by nucleophilic reaction. As the hindered amine compound serves as an optical stabilizer of a high-molecular polymer, the hindered amine compound is not easy to dissolve and separate as the end alkene groups containing unsaturated bonds can be grafted to a high-molecular chain through a radiotechnology to form a carbon-carbon bond, so that the optical stability is enhanced.

Description

technical field [0001] The invention belongs to the technical field of additives, in particular to a hindered amine compound and a preparation method thereof. Background technique [0002] When polymer materials are exposed to sunlight or strong fluorescence, photooxidation reactions are prone to occur, resulting in polymer degradation, which reduces the appearance and physical and mechanical properties of polymer materials. In addition to improving the polymerization process and product structure, the current measure to prevent photooxidation is to add light stabilizers. As a kind of polymer material additive, light stabilizer has the characteristics of inhibiting or slowing down photodegradation and improving the light resistance of materials. Its dosage is very small, usually only 0.01%~0.5% of the weight of polymer materials. The mechanism of action of light stabilizers is mainly divided into three types: shielding, reflecting ultraviolet rays or absorbing ultraviolet r...

Claims

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Application Information

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IPC IPC(8): C07D401/14C08G73/06C08K5/3492C08L79/04
CPCY02P20/55
Inventor 郑春柏邓鹏飏尹园柳美华魏巍
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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