Methylphenyl methoxy phosphine heterocyclic methyl silicate compound and preparation method thereof

Abstract

The invention relates to a methylphenyl methoxy silicic acid phosphine heterocylic methyl ester compound as a fire retardant and a preparation method thereof. The structure of the compound is shown in the following formula (as shown in the description). The preparation method comprises the following steps of under nitrogen protection, controlling the molar ratio of 4-ethyl-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane to methylphenyl dimethoxysilanes to be 1:1 to1:1.4; under the action of a catalyst, enabling the temperature to rise to 120-170 DEG C, and performing a heat insulating reaction for 11-17 hours; and through purification treatment, obtaining methylphenyl methoxy silicic acid phosphine heterocylic methyl ester. The product disclosed by the invention is suitable for being used as the fire retardant of materials of unsaturated resins, polyvinyl chloride, polyurethane, epoxy resins, furan resins and the like. The production technology is simple, the equipment investment is low, and the industrialized production is easy to realize.

Description

technical field

[0001] The invention relates to an organosilicon-phosphorus flame retardant methylphenylmethoxyphosphine heterocyclic methyl silicate compound and a preparation method thereof, in particular to an organosilicon-phosphorus flame retardant methylphenylmethoxyl (1 -Oxygen-1-methyl-4-ethyl-1-phospha-2,6-dioxa-cyclohexyl-<4>-methoxy)silane compound and its preparation method, the compound contains phosphorus Silicon and phosphorus are dual flame retardant elements, phosphorus and silicon synergistically have high flame retardant performance, and are suitable for use as flame retardants for unsaturated resins, polyvinyl chloride, polyurethane, epoxy resins, furan resins and other materials. Background technique

[0002] Organophosphorus flame retardants, due to their excellent flame retardant performance and environmental friendliness, have been rapidly developed in recent years amid calls for non-halogenated flame retardants. Among them, phosphate ester fla...

Examples

Embodiment 1

[0028] Example 1 In a 200ml four-neck flask equipped with a stirrer, a thermometer, and a high-efficiency reflux condenser, replace the air in the bottle with nitrogen, and add 16.21g (0.10mol) of caged phosphate ester and 80ml of diethylene glycol dimethyl ether , 21.88g (0.12mol) methylphenyldimethoxysilane and 0.40g dimethyl sulfate, heat up to 160°C, keep the temperature for 13h, then cool to 50°C, transfer to a separatory funnel to stand for layering, Separate the lower layer of feed liquid, then add 35ml of toluene to wash, let stand to separate the lower layer of feed liquid, and then distill under reduced pressure to remove toluene and a small amount of low boiling point substances to obtain a light yellow liquid methyl phenyl methoxyphosphine heterocyclic methyl silicate , product yield 86.0%, its flash point (open cup): 207±5°C, decomposition temperature: 302±5°C, density (25°C): 1.734g / cm 3 , Refractive index: n D 25 = 1.4725.

Embodiment 2

[0029] Example 2 In a 100ml four-necked flask equipped with a stirrer, a thermometer, and a high-efficiency reflux condenser, the air in the bottle was replaced with nitrogen, and 16.21g (0.10mol) of caged phosphate, 20.05g (0.11mol) of methyl Phenyldimethoxysilane and 0.49g dimethyl sulfate, heat up to 170°C, keep warm for 11h, then cool to 50°C, add 35ml of toluene to wash, let stand to separate the lower layer of material liquid, and then distill under reduced pressure to remove toluene and A small amount of low-boiling matter, to obtain light yellow liquid methyl phenyl methoxyphosphonomethyl heterocyclic methyl silicate, the product yield is 84.6%, its flash point (open cup): 207±5°C, decomposition temperature: 302±5°C , Density (25°C): 1.734g / cm 3 , Refractive index: n D 25 = 1.4725.

Embodiment 3

[0030]Example 3 In a 200ml four-necked flask equipped with a stirrer, a thermometer, and a high-efficiency reflux condenser, replace the air in the bottle with nitrogen, and add 16.21g (0.10mol) of caged phosphate ester, 60mlDMF, 25.52g (0.14mol) Methylphenyldimethoxysilane and 0.35g methyl p-toluenesulfonate, heat up to 140°C, keep warm for 14h, then cool to 50°C, transfer to a separatory funnel to stand for stratification, and separate the lower layer of material liquid , then add 35ml of toluene to wash, let stand to separate the lower layer of feed liquid, then distill under reduced pressure to remove toluene and a small amount of low boiling point, to obtain light yellow liquid methyl phenyl methoxy phosphine heterocyclic methyl silicate, the product yield is 90.3 %, its flash point (open cup): 207±5°C, decomposition temperature: 302±5°C, density (25°C): 1.734g / cm 3 , Refractive index: n D 25 = 1.4725.

technical field

[0001] The invention relates to an organosilicon-phosphorus flame retardant methylphenylmethoxyphosphine heterocyclic methyl silicate compound and a preparation method thereof, in particular to an organosilicon-phosphorus flame retardant methylphenylmethoxyl (1 -Oxygen-1-methyl-4-ethyl-1-phospha-2,6-dioxa-cyclohexyl-<4>-methoxy)silane compound and its preparation method, the compound contains phosphorus Silicon and phosphorus are dual flame retardant elements, phosphorus and silicon synergistically have high flame retardant performance, and are suitable for use as flame retardants for unsaturated resins, polyvinyl chloride, polyurethane, epoxy resins, furan resins and other materials. Background technique

[0002] Organophosphorus flame retardants, due to their excellent flame retardant performance and environmental friendliness, have been rapidly developed in recent years amid calls for non-halogenated flame retardants. Among them, phosphate ester fla...

Examples

Embodiment 1

[0028] Example 1 In a 200ml four-neck flask equipped with a stirrer, a thermometer, and a high-efficiency reflux condenser, replace the air in the bottle with nitrogen, and add 16.21g (0.10mol) of caged phosphate ester and 80ml of diethylene glycol dimethyl ether , 21.88g (0.12mol) methylphenyldimethoxysilane and 0.40g dimethyl sulfate, heat up to 160°C, keep the temperature for 13h, then cool to 50°C, transfer to a separatory funnel to stand for layering, Separate the lower layer of feed liquid, then add 35ml of toluene to wash, let stand to separate the lower layer of feed liquid, and then distill under reduced pressure to remove toluene and a small amount of low boiling point substances to obtain a light yellow liquid methyl phenyl methoxyphosphine heterocyclic methyl silicate , product yield 86.0%, its flash point (open cup): 207±5°C, decomposition temperature: 302±5°C, density (25°C): 1.734g / cm 3 , Refractive index: n D 25 = 1.4725.

Embodiment 2

[0029] Example 2 In a 100ml four-necked flask equipped with a stirrer, a thermometer, and a high-efficiency reflux condenser, the air in the bottle was replaced with nitrogen, and 16.21g (0.10mol) of caged phosphate, 20.05g (0.11mol) of methyl Phenyldimethoxysilane and 0.49g dimethyl sulfate, heat up to 170°C, keep warm for 11h, then cool to 50°C, add 35ml of toluene to wash, let stand to separate the lower layer of material liquid, and then distill under reduced pressure to remove toluene and A small amount of low-boiling matter, to obtain light yellow liquid methyl phenyl methoxyphosphonomethyl heterocyclic methyl silicate, the product yield is 84.6%, its flash point (open cup): 207±5°C, decomposition temperature: 302±5°C , Density (25°C): 1.734g / cm 3 , Refractive index: n D 25 = 1.4725.

Embodiment 3

[0030]Example 3 In a 200ml four-necked flask equipped with a stirrer, a thermometer, and a high-efficiency reflux condenser, replace the air in the bottle with nitrogen, and add 16.21g (0.10mol) of caged phosphate ester, 60mlDMF, 25.52g (0.14mol) Methylphenyldimethoxysilane and 0.35g methyl p-toluenesulfonate, heat up to 140°C, keep warm for 14h, then cool to 50°C, transfer to a separatory funnel to stand for stratification, and separate the lower layer of material liquid , then add 35ml of toluene to wash, let stand to separate the lower layer of feed liquid, then distill under reduced pressure to remove toluene and a small amount of low boiling point, to obtain light yellow liquid methyl phenyl methoxy phosphine heterocyclic methyl silicate, the product yield is 90.3 %, its flash point (open cup): 207±5°C, decomposition temperature: 302±5°C, density (25°C): 1.734g / cm 3 , Refractive index: n D 25 = 1.4725.

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