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Novel hindered amine light stabilizers, and preparation method and applications thereof

A technology of light stabilizers and hindered amines, applied in the field of light stabilizers and their synthesis, to achieve the effects of high yield, improved physical properties, and simple operation

Active Publication Date: 2019-09-27
SHAOXING RUIKANG BIOTECHNOLOGES CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to provide a novel hindered amine light stabilizer and its preparation method aiming at the technical deficiencies such as the structure and performance of existing market products

Method used

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  • Novel hindered amine light stabilizers, and preparation method and applications thereof
  • Novel hindered amine light stabilizers, and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0022] 3.97g (10.06mmol) hexamethylenediaminepiperidine (the situation where n of the compound of formula 1 is 5) is dissolved in 20ml dry solvent (DCM, or THF or ethyl acetate or MTBE, or acetone), add 21.12mmol acid-binding agent ( Anhydrous potassium carbonate or NaOH or Na2CO3 or NEt3), under the protection of N2, the temperature of the ice-salt bath is reduced to -10°C, and 2.82g of benzoyl chloride (when the compound R of formula 2 is -Ph) is added dropwise, and the dropwise addition is completed in about 30 minutes. Stir at zero for 1 h, allow to warm up to room temperature and stir for 6 h, filter, recover the solvent under reduced pressure at 40°C, recrystallize to obtain 5.8 g of white solid, yield: 96%.

[0023] 1 H-NMR / CDCl 3 / 400MHz: δ7.346~7.423ppm(t,J=5.1Hz,5H),3.150~3.343ppm(s,2H),4.026ppm(s,1H)

[0024] MS (ESI+): theoretical 602.9; measured 302.40, 603.37, 604.31, 1205.00, 1227.16, 1229.12.

example 2

[0026] 3.97g (10.06mmol) hexamethylenediamine piperidine is dissolved (the situation that formula 1 compound n is 5) in 20ml dry solvent (DME or THF or acetone or ethyl acetate or toluene or MTBE), add 21.12mmol acid-binding agent ( Anhydrous NaOH or K2CO3 or NEt3 or pyridine or Na2CO3), the temperature of the ice-salt bath under N2 protection is down to-10 ℃, and 3.25g o-fluorobenzoyl chloride (compound R of formula 2 is ) dropwise, stirred at zero for 1 h, allowed to warm up to room temperature and stirred for 10 h, TLC followed the reaction until the reaction was complete and filtered, recovered the solvent under reduced pressure at 40°C, recrystallized to obtain 6 g of off-white solid, yield: 94%. 1 H-NMR / CDCl 3 / 400MHz: δ7.37ppm (dd, J = 13.3, 5.9Hz, 1H), 7.34~7.28ppm (m, 1H), 7.20ppm (t, J = 7.5Hz, 1H), 7.11ppm (t, J = 8.8 Hz, 1H), δ3.86ppm (t, J=11.9Hz, 1H), δ3.36ppm (d, J=54.4Hz, 2H)

[0027] MS (ESI+): theoretical 638.9; measured: 320.39, 639.54, 1276.94.

example 3

[0029] 3.97g (10.06mmol) hexamethylenediamine piperidine is dissolved (the situation that formula 1 compound n is 5) in 20ml dry solvent (MTBE or THF or DME or acetone or ethyl acetate), add 21.12mmol acid-binding agent (NaCO Or K2CO3 or NaOH), under N2 protection, the temperature of the ice-salt bath is down to-10°C, and slowly add 3.5g p-methoxybenzoyl chloride dropwise (compound R of formula 2 is In the case of the reaction), the dropwise addition was completed in about 30 minutes, stirred at zero for 1 hour, allowed to rise naturally to room temperature and stirred for 6-18 hours, TLC followed the reaction until the reaction was complete and filtered, the solvent was recovered under reduced pressure at 40°C, recrystallized to obtain 6.5 g of a white solid, and The rate is 98%.

[0030] 1 H-NMR / CDCl 3 / 400MHz: δ6.92ppm (d, J = 8.5Hz, 1H), 3.83ppm (s, 1H), 3.32ppm (s, 1H)

[0031] MS(ESI+): Theory 663.0; Measured: 332.48, 663.63, 1325.14, 1347.57

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Abstract

The invention relates to novel hindered amine light stabilizers, and a preparation method and applications thereof. According to the preparation method, light stabilizers with high matching performance with high molecular materials of different polarities are obtained through adjusting the length of fat alkyl side chains in designed structures; and light stabilizers with different ultraviolet light absorption ranges are obtained through adjusting aromatic substituent groups in designed structures. The hindered amine light stabilizers with adjustable matching performance and light adsorbing light stabilizing synergistic performance are suitable for photodegradation protection of various high molecular materials. The preparation method comprises following steps: a compound represented by formula 1 is dissolved in a dry solvent; under N2 protection, an acid binding agent is added, ice salt bath is adopted to maintain the temperature to be constant, a compound represented by formula 2 is added dropwise in a certain time period, and stirring is carried out so as to obtain a crude product of a compound represented by formula 3. The novel hindered amine light stabilizers disclosed in the invention are capable of solving some problems of the matching performance and migration of conventional hindered amine light stabilizers.

Description

technical field [0001] The invention relates to a novel hindered amine light stabilizer and its preparation method and application, and belongs to the field of novel light stabilizers with high compatibility with polymer materials and their synthesis. Background technique [0002] Hindered Amine Light Stabilizer (HALS for short) is an efficient additive for inhibiting photooxidative degradation of polymer materials, and its light stabilizing effect is 2-4 times that of traditional absorbing light stabilizers. Since there are many different types of auxiliary groups and substituents, their varieties are diversified. For example, functionalized hindered amines are bonded to hindered amine light stabilizers with functional groups such as ultraviolet absorption, thermal oxidation resistance, and peroxide decomposition, so that one agent can be used for multiple purposes. [0003] Conventional HALS products such as UV-3853, UV-770, etc. have the disadvantages of being not resist...

Claims

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Application Information

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IPC IPC(8): C07D211/58C08K5/3435C08L23/12C08L23/06C08L23/00C08L55/02C08L25/06C08L67/02
CPCC07D211/58C08K5/3435C08L23/12C08L23/06C08L23/00C08L55/02C08L25/06C08L67/02C08L2201/08Y02P20/54
Inventor 毛丽娟尹奇伟陈刚波王以菲陈秀颖丁轶凡刘树柏
Owner SHAOXING RUIKANG BIOTECHNOLOGES CO INC
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