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Preparation method of polymeric type HALS (Hindered Amine Light Stabilizer) HA-88

A technology of HA-88 and hindered amines, which is applied in the field of functional additives for polymer materials, can solve problems such as the difficulty of molecular weight regulation, achieve the effect of optimizing molecular weight distribution and improving the difficulty of molecular weight regulation

Active Publication Date: 2019-03-22
RIANLON +3
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The purpose of the present invention is to address the deficiencies in the prior art and provide a method for preparing a polymeric hindered amine light stabilizer HA-88. The synthesis method is easier to control and improves the molecular weight of similar polymeric hindered amine light stabilizers in the past. Difficult to control, optimize the molecular weight distribution of HA-88, and improve product quality

Method used

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  • Preparation method of polymeric type HALS (Hindered Amine Light Stabilizer) HA-88
  • Preparation method of polymeric type HALS (Hindered Amine Light Stabilizer) HA-88

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Embodiment 1

[0031] The preparation of embodiment 1 HA-88

[0032]Add 1.39g (8mmol) N,N'-bis(3-aminopropyl)ethylenediamine and 20mL toluene to the three-necked flask, drop 0.74g (4mmol) trimeric Add 0.9 mL of 30% sodium hydroxide aqueous solution to the reaction liquid after the dropwise addition of 5 mL of toluene solution of cyanogen chloride, continue to react in ice bath for 2 h, then raise the temperature to 45° C. for 4 h. After the reaction of this stage was completed, the ice bath was down to 10°C, and 25mL of toluene solution of 3.69g (20mmol) cyanuric chloride was added dropwise thereto. Insulation reaction under the bath for 6h. After the reaction at this stage is completed, add 9.34g (44mool) N-butyl-2,2,6,6-tetramethyl-4-piperidinamine and 4.5mL 30% sodium hydroxide aqueous solution to the system, and heat up to 45 °C for 3 hours, then continue to heat up to reflux for 4 hours. The reaction solution was washed with water and the solvent was distilled off under reduced press...

Embodiment 2

[0034] The preparation of embodiment 2 HA-88

[0035] Add 1.39g (8mmol) N,N'-bis(3-aminopropyl)ethylenediamine and 20mL xylene to the three-necked flask, drop 0.74g (4mmol) Tris Add 0.7 g (8.3 mmol) of sodium bicarbonate to the reaction liquid after the dropwise addition of 5 mL of toluene solution of polycyanogen chloride, continue to react in ice bath for 2 h, then raise the temperature to 45° C. for 4 h. After the reaction of this stage was completed, the ice bath was down to 10°C, and 25mL of toluene solution of 2.95g (16mmol) cyanuric chloride was added dropwise thereto, and 1.4g (16.6mmol) sodium bicarbonate was added in the reaction solution after the dropwise addition. The reaction was incubated for 8 hours in an ice bath. After the reaction at this stage was completed, 7.65g (36mool) N-butyl-2,2,6,6-tetramethyl-4-piperidinamine and 3.1g (37mmol) sodium bicarbonate were added to the system, and the temperature was raised to 45 °C for 3 hours, then continue to heat up...

Embodiment 3

[0037] The preparation of embodiment 3 HA-88

[0038] Add 1.39g (8mmol) N,N'-bis(3-aminopropyl)ethylenediamine and 20mL xylene to the three-necked flask, drop 0.81g (4.4mmol) into the solution after the ice bath is lowered to 10°C After the 5mL toluene solution of cyanuric chloride was added dropwise, 0.9mL of 30% sodium hydroxide aqueous solution was added to the reaction solution, and the reaction was continued for 2h under ice-bath conditions, and then the temperature was raised to 45°C for 4h. After the completion of the reaction at this stage, the ice bath was down to 10°C, and 25mL of toluene solution of 3.32g (18mmol) cyanuric chloride was added dropwise thereto, and 2.2mL of 30% aqueous sodium hydroxide solution was added to the reaction solution after the dropwise addition was completed. Insulation reaction under the bath for 6h. After the reaction at this stage is completed, add 8.58g (40.4mool) N-butyl-2,2,6,6-tetramethyl-4-piperidinamine and 4.5mL30% sodium hydrox...

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Abstract

The invention provides a preparation method of a polymeric type HALS (Hindered Amine Light Stabilizer) HA-88. The preparation method comprises the following steps: enabling N.N'-bis(3-aminopropyl)ethanediamine to react with a first part of cyanuric chloride, thus generating 6-chloro-1,3,5-triazine-2,4-bis(1,5,8,12-tetraaza n-dodecane); then adding a second part of cyanuric chloride for carrying out condensation reaction; finally terminating by using N-butyl-2,2,6,6-tetramethyl-4-piperidylamine. According to the preparation method provided by the invention, a new synthesis route is adopted, a synthesis technology of the HA-88 can be easily controlled, the problem that the molecular weight of a similar polymeric type HALS in the past is difficult to regulate and control is improved, molecular weight distribution is optimized, and the product quality is increased.

Description

technical field [0001] The invention relates to the field of polymer material functional additives, in particular to a preparation method of a polymeric hindered amine light stabilizer, more specifically, to the preparation of a polymeric hindered amine light stabilizer HA-88. 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. This type of substance has a good synergistic effect with ultraviolet absorbers and antioxidants, and has good compatibility with various polymer materials. Due to its good application performance, HALS has been an important development in the field of polymer anti-aging since its inception, and it is also the fastest-growing class of high-efficiency light stabilizers. [0003] Due to its relatively low molecular weight, the early HALS product...

Claims

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Application Information

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IPC IPC(8): C07D401/14C08K5/3492
CPCC07D401/14C08K5/34926
Inventor 王梓范小鹏管波孙春光李海平郭平武
Owner RIANLON
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