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Hydroxymethylphosphonoheterocyclic phenylthiophosphonate compound and preparation method thereof

A technology of phenyl thiophosphonate and hydroxymethyl phosphono, which is applied in the field of hydroxymethyl phosphono heterocyclic phenyl thiophosphonate compound and preparation thereof, and can solve the problem of deterioration of mechanical properties of materials and flame retardancy. The problems of poor effect and large amount of addition can achieve the effect of easy large-scale conversion and production, less equipment investment, and increased phosphorus content.

Active Publication Date: 2017-12-22
HUZHOU RUIGAO NEW MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although halogen-based flame retardants have the advantages of small addition amount and high flame-retardant efficiency, they will produce toxic fumes and cause secondary damage to the human body when burned.
Inorganic flame retardants have good stability and are non-toxic, but the flame retardant effect is poor and the addition amount is large, which will deteriorate the mechanical properties of the material, and there are many deficiencies

Method used

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  • Hydroxymethylphosphonoheterocyclic phenylthiophosphonate compound and preparation method thereof
  • Hydroxymethylphosphonoheterocyclic phenylthiophosphonate compound and preparation method thereof
  • Hydroxymethylphosphonoheterocyclic phenylthiophosphonate compound and preparation method thereof

Examples

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Effect test

Embodiment 1

[0028] Example 1 In a 100ml four-necked flask equipped with a stirrer, a thermometer, a high-efficiency reflux condenser and a hydrogen chloride absorption device connected to the upper mouth of the condenser, the air in the bottle was driven away with nitrogen, and 30ml of diethylene glycol dimethyl was added. Ether, 14.00g (0.1mol) of trimethylolphosphine oxide, under stirring, at 20°C, add dropwise 21.10g (0.1mol) of phenylphosphonothioate dichloride, make it fully mixed, and heat up to 75°C, Hydrogen chloride begins to be released, heat up to 100°C for 2 hours, then heat up to 160°C for 5 hours, wait until no hydrogen chloride is released, remove diethylene glycol dimethyl ether (recycled) by vacuum distillation, cool down to below 20°C, and then add 55ml of ice water, under stirring, 5% sodium carbonate solution was added dropwise to make the pH of the reaction system = 7, allowed to stand for stratification, the lower layer material liquid was separated, and a small amoun...

Embodiment 2

[0029] Example 2 In a 100ml four-necked flask equipped with a stirrer, a thermometer, a high-efficiency reflux condenser and connected to a hydrogen chloride absorption device on the condenser, the air in the bottle was driven away with nitrogen, and 40ml of anisole was added, 14.00g (0.1mol) trimethylolphosphine oxide, under stirring, at 20°C, add dropwise 21.10g (0.1mol) phenylphosphonothioate dichloride, mix well, heat up to 75°C, hydrogen chloride begins to be released , heat up to 100°C for 2 hours, then heat up to 150°C for 6 hours, wait until no hydrogen chloride is released, remove anisole (recycled) by distillation under reduced pressure, cool down to below 20°C, add 50ml of ice water, stir, drop Add 5% sodium carbonate solution to make the pH of the reaction system = 7, let it stand for stratification, separate the lower layer of material liquid, and distill under reduced pressure to remove a small amount of water in the material to obtain a colorless viscous liquid h...

Embodiment 3

[0030]Example 3 In a 150ml four-necked flask equipped with a stirrer, a thermometer, a high-efficiency reflux condenser and connected to a hydrogen chloride absorption device on the condenser, the air in the bottle was driven away with nitrogen, and 50ml xylene was added, and 14.00g ( 0.1mol) of trishydroxymethylphosphine oxide, under stirring, at 20°C, add dropwise 21.10g (0.1mol) of phenylphosphonothioate dichloride, make it fully mixed, heat up to 75°C, hydrogen chloride begins to be released, Raise the temperature to 100°C for 2 hours, then raise the temperature to 140°C for 7 hours, wait until no hydrogen chloride is released, remove xylene by vacuum distillation (recycling), lower the temperature to below 20°C, add 40ml of ice water, stir, and drop 5 % sodium carbonate solution to make the pH of the reaction system = 7, let it stand for stratification, separate the lower layer material liquid, and remove a small amount of water in the material by distillation under reduce...

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Abstract

The invention relates to a flame retardant hydroxymethylphosphonoheterocyclic phenylthiophosphonate compound and a preparation method thereof. The structure of the compound is shown in the following formula: The preparation method is: under nitrogen protection, at 20°C, Mix equimolar trishydroxymethyl phosphine oxide and phenylphosphonothiodichloride thoroughly, raise the temperature to 100°C for 2 hours, then raise the temperature to 130-160°C for 5-9 hours, exhaust the hydrogen chloride, and purify. Obtain hydroxymethylphosphono heterocyclic phenylthiophosphonate. The compound of the invention has high phosphorus content and excellent phosphorus-sulfur synergistic flame-retardant performance, and is suitable for use as a flame-retardant for unsaturated resin, polyvinyl alcohol, polyurethane, epoxy resin and the like. And the preparation method is one-step reaction, the process is simple, the equipment investment is small, and the industrialized production is easy to realize.

Description

technical field [0001] The invention relates to an organic phosphine flame retardant hydroxymethylphosphono heterocyclic phenylthiophosphonate compound and a preparation method thereof, in particular to a 1-thio-4-oxo-1-phenyl-4 - hydroxymethyl-2,6-dioxa-1,4-diphosphorinane compound and its preparation method, the compound is suitable as a flame retardant for unsaturated resins, polyvinyl alcohol and epoxy resins; It is used as a reactive flame retardant for polyurethane; it can also be used as an intermediate in organic synthesis. Background technique [0002] With the rapid development of engineering plastics technology, there are more and more researches on the modification of high-performance flame-retardant materials. The flame retardants commonly used in engineering plastics can be divided into halogen-based, phosphorus-based and inorganic flame retardants. Although halogen-based flame retardants have the advantages of small addition amount and high flame-retardant e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6574C08K5/5398C08L101/00
Inventor 王彦林杨珂珂
Owner HUZHOU RUIGAO NEW MATERIALS CO LTD