Siliceous N-substituted alkyloxy hindered amine compound and its preparation method

Abstract

The invention discloses a siliceous N-substituted alkyloxy hindered amine compound and its preparation method, wherein the constitutional unit of the compound is as shown in the formula I. In the formula I, X is the element O or group R, wherein the structural formula of the group R is as shown in the formula II. In the formula II, the general formula of R1 is -HN(CH2CH2NH)n(CH2)3-, wherein n is 0-2; R2 is an alkyl group, the general formula of which is -CmH2m+1, wherein m is1-8; R3 is an alkyl group, the general formula of which is -CkH2k-, wherein k is 1-6; R4 and R5 respectively represent an alkyl group, of which the general formula is -CiH2i+1 or a cycloalkyl group, of which the general formula is -CtH2t, wherein i is 1-8 and t is 1-8. The compound simultaneously has flame-retardation synergy, light stability and compatibilization, can be used to raise flame retardation of a flame-retardation polymer and simultaneously further improve its light stability, mechanical property and the like.

Description

technical field

[0001] The invention relates to a hindered amine flame retardant synergist and a synthesis method thereof, in particular to a silicon-containing N-substituted alkoxy hindered amine compound and a synthesis method thereof. Background technique

[0002] In recent years, hindered amines, which have long been used as light stabilizers, have found that N-substituted alkoxy hindered amines have excellent flame retardant properties in the process of performance improvement. N-substituted alkoxy hindered amine, as one of the improved varieties of hindered amine, has the characteristics of low reactivity, and its general chemical structure is:

[0003]

[0004] Wherein, A is an auxiliary group connecting piperidinyl, and B is a substituted alkyl group.

[0005] The flame retardant effect of N-substituted alkoxy hindered amines in polyolefins is mainly due to the high-efficiency recyclable free radical scavenger produced by combustion decomposition to interfere and...

Examples

Embodiment 1

[0034]Add 7.376g (0.04mol) of cyanuric chloride dissolved in 80ml of acetone into a 500m1 reaction kettle equipped with a thermometer and a magnet (magnetic stirrer). The temperature of the reaction system was kept at -10°C. 7.572g (0.01mol) of the first compound (wherein, R 2 for alkyl-C 2 h 5 , R 3 for alkyl-C 2 h 4 -, R 4 is alkyl-CH 4 , R 5 Cycloalkyl-C 3 h 6 ) and 8.70ml of acid-binding agent N,N-isopropylethane (0.05mol) were dissolved in 30ml of acetone, and were added dropwise into the reaction kettle with a micro-injector to control the rate of addition, and the reaction temperature was controlled at -10 At ℃, a substitution reaction of the chlorine atom on the triazine ring on the cyanuric chloride is carried out. After the dropwise addition, the reaction was continued at -10° C. for 5 h at a low temperature, and the pH of the reaction solution was 6.0 at this time. Finally, pour the solution in the reaction kettle into a 250ml three-necked flask and move...

Embodiment 2

[0056] Add 3.688g (0.02mol) of cyanuric chloride dissolved in 80ml of methyl ethyl ketone into a 500m1 reaction kettle equipped with a thermometer and a magnet (magnetic stirrer), control the temperature in a low-temperature thermostat and fully stir to make the reactants evenly dispersed And keep the temperature of the reaction system at 10°C. 7.572g (0.01mol) of the first compound (wherein, R 2 for alkyl-C 2 h 5 , R 3 for alkyl-C 2 h 4 -, R 4 is alkyl-CH 4 , R 5 Cycloalkyl-C 3 h 6 ) and 15ml of acid-binding agent NaOH aqueous solution (2.0mol / L) were dissolved in 30ml of methyl ethyl ketone, and were added drop by drop to the reaction kettle at the same time with a micro-injector to control the rate of addition, and the reaction temperature was controlled at 10°C. A substitution reaction of the chlorine atom on the triazine ring on the polycyanogen chloride. After the dropwise addition, the reaction was continued at a low temperature of 10° C. for 2 h, and the pH ...

Embodiment 3

[0068] Add 1.844g (0.01mol) of cyanuric chloride dissolved in 80ml of acetone into a 500m1 reaction kettle equipped with a thermometer and a magnet (magnetic stirrer). The temperature of the reaction system was kept at 5°C. 7.572g (0.01mol) of the first compound (wherein, R 2 for alkyl-C 2 h 5 , R 3 for alkyl-C 2 h 4 -, R 4 is alkyl-CH 4 , R 5 Cycloalkyl-C 3 h 6 ) and 0.870ml of acid-binding agent N,N-isopropylethane (0.005mol) were dissolved in 30ml of acetone, and were added dropwise into the reaction kettle with a micro-injector to control the rate of addition, and the reaction temperature was controlled at 5°C Next, carry out a substitution reaction of the chlorine atom on the triazine ring on the cyanuric chloride. After the dropwise addition, the reaction was continued at 5° C. for 3 h at a low temperature, and the pH of the reaction solution was 6.5 at this time. Finally, pour the solution in the reaction kettle into a 250ml three-necked flask and move it to...

technical field

[0001] The invention relates to a hindered amine flame retardant synergist and a synthesis method thereof, in particular to a silicon-containing N-substituted alkoxy hindered amine compound and a synthesis method thereof. Background technique

[0002] In recent years, hindered amines, which have long been used as light stabilizers, have found that N-substituted alkoxy hindered amines have excellent flame retardant properties in the process of performance improvement. N-substituted alkoxy hindered amine, as one of the improved varieties of hindered amine, has the characteristics of low reactivity, and its general chemical structure is:

[0003]

[0004] Wherein, A is an auxiliary group connecting piperidinyl, and B is a substituted alkyl group.

[0005] The flame retardant effect of N-substituted alkoxy hindered amines in polyolefins is mainly due to the high-efficiency recyclable free radical scavenger produced by combustion decomposition to interfere and...

Examples

Embodiment 1

[0034]Add 7.376g (0.04mol) of cyanuric chloride dissolved in 80ml of acetone into a 500m1 reaction kettle equipped with a thermometer and a magnet (magnetic stirrer). The temperature of the reaction system was kept at -10°C. 7.572g (0.01mol) of the first compound (wherein, R 2 for alkyl-C 2 h 5 , R 3 for alkyl-C 2 h 4 -, R 4 is alkyl-CH 4 , R 5 Cycloalkyl-C 3 h 6 ) and 8.70ml of acid-binding agent N,N-isopropylethane (0.05mol) were dissolved in 30ml of acetone, and were added dropwise into the reaction kettle with a micro-injector to control the rate of addition, and the reaction temperature was controlled at -10 At ℃, a substitution reaction of the chlorine atom on the triazine ring on the cyanuric chloride is carried out. After the dropwise addition, the reaction was continued at -10° C. for 5 h at a low temperature, and the pH of the reaction solution was 6.0 at this time. Finally, pour the solution in the reaction kettle into a 250ml three-necked flask and move...

Embodiment 2

[0056] Add 3.688g (0.02mol) of cyanuric chloride dissolved in 80ml of methyl ethyl ketone into a 500m1 reaction kettle equipped with a thermometer and a magnet (magnetic stirrer), control the temperature in a low-temperature thermostat and fully stir to make the reactants evenly dispersed And keep the temperature of the reaction system at 10°C. 7.572g (0.01mol) of the first compound (wherein, R 2 for alkyl-C 2 h 5 , R 3 for alkyl-C 2 h 4 -, R 4 is alkyl-CH 4 , R 5 Cycloalkyl-C 3 h 6 ) and 15ml of acid-binding agent NaOH aqueous solution (2.0mol / L) were dissolved in 30ml of methyl ethyl ketone, and were added drop by drop to the reaction kettle at the same time with a micro-injector to control the rate of addition, and the reaction temperature was controlled at 10°C. A substitution reaction of the chlorine atom on the triazine ring on the polycyanogen chloride. After the dropwise addition, the reaction was continued at a low temperature of 10° C. for 2 h, and the pH ...

Embodiment 3

[0068] Add 1.844g (0.01mol) of cyanuric chloride dissolved in 80ml of acetone into a 500m1 reaction kettle equipped with a thermometer and a magnet (magnetic stirrer). The temperature of the reaction system was kept at 5°C. 7.572g (0.01mol) of the first compound (wherein, R 2 for alkyl-C 2 h 5 , R 3 for alkyl-C 2 h 4 -, R 4 is alkyl-CH 4 , R 5 Cycloalkyl-C 3 h 6 ) and 0.870ml of acid-binding agent N,N-isopropylethane (0.005mol) were dissolved in 30ml of acetone, and were added dropwise into the reaction kettle with a micro-injector to control the rate of addition, and the reaction temperature was controlled at 5°C Next, carry out a substitution reaction of the chlorine atom on the triazine ring on the cyanuric chloride. After the dropwise addition, the reaction was continued at 5° C. for 3 h at a low temperature, and the pH of the reaction solution was 6.5 at this time. Finally, pour the solution in the reaction kettle into a 250ml three-necked flask and move it to...

Images