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Method for producing aromatic diphosphates

一种二磷酸酯、制造方法的技术，应用在有机化学方法、化学仪器和方法、周期表第5/15族元素的化合物等方向，能够解决树脂分子量降低、主成分纯度降低、阻燃效果低等问题，达到机械物性的降低抑制、优异耐久性、不易劣化的效果

Inactive Publication Date: 2013-03-20
DIAHACHI CHEMICAL INDUSTRY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these halogen-containing compounds have the following problems: hydrogen halide is generated by thermal decomposition during resin molding, which corrodes the mold, deteriorates the resin itself, causes coloring, and deteriorates the operating environment.
However, these inorganic-based compounds and nitrogen-based compounds have the following problems: the flame-retardant effect is significantly low, and a large amount needs to be added in order to obtain a sufficient effect, thereby impairing the original physical properties of the resin.
[0013] When aromatic bisphosphate ester containing this by-product is added as a flame retardant to thermoplastic resins such as polycarbonate, transesterification reactions occur during molding processing and react with the molecular ends of the thermally decomposed resin , In the long-term use of the resin molded product, it gradually causes adverse effects, etc., thereby reducing the molecular weight of the resin, and as a result, there is a problem that the durability, physical properties, water resistance, hydrolysis resistance, and heat resistance of the resin molded product are reduced.
[0014] In addition, there is also a problem that this by-product undergoes transesterification with the aromatic diphosphate as the main component under high-temperature conditions such as molding processing, resulting in a further increase in by-products and a decrease in the purity of the main component.
[0016] However, in the additive type flame retardant having the aromatic diphosphate represented by the general formula (I) as the main component of the present invention, the compound having a hydroxyphenyl group represented by the general formula (II) of the present invention will cause problems as mentioned above and thus not preferred

Method used

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  • Method for producing aromatic diphosphates
  • Method for producing aromatic diphosphates
  • Method for producing aromatic diphosphates

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0137] 1. The first process

[0138] In a 1-liter four-neck flask equipped with a stirrer, a thermometer, a dropping device (funnel) and a hydrochloric acid recovery device (a condenser connected to a water scrubber), 244 g of 2,6-xylenol was filled as an aromatic monohydroxy Compound (III), 20 g of xylene as a solvent, and 1.5 g of magnesium chloride as a catalyst. The obtained mixed solution was heated while stirring, and when the temperature of the mixed solution reached 120° C., 153 g of phosphorus oxychloride was added dropwise over about 2 hours. After completion of the addition, the reaction was carried out by heating gradually until the temperature of the mixed solution reached 180° C. over 2 hours, and 68 g of hydrogen chloride (hydrochloric acid gas) generated was collected from a water scrubber. Then, at the same temperature (180° C.), the pressure in the flask was slowly reduced to 20 kPa, and unreacted phosphorus oxychloride and xylene were removed in 1 hour to o...

Embodiment 2

[0156] A 20-liter four-neck flask was used as a reaction vessel, 5856 g of 2,6-xylenol was used as an aromatic monohydroxy compound (III), 480 g of xylene was used as a solvent, 36 g of magnesium chloride was used as a catalyst, and 3672 g of phosphorus oxychloride was used. In addition, it carried out similarly to the 1st process of Example 1, and obtained the reaction mixture 7741g containing bis(2,6-xylyl) chlorophosphate as a diaryl halophosphate (IV). In addition, the chlorine content of the reaction mixture was 10.6% by weight.

[0157] In addition, except that 1273g of resorcinol was used as the aromatic dihydroxy compound (V) and 101g of aluminum chloride as an additional catalyst, the second step of Example 1 was performed in the same manner to obtain aromatic diphosphate (I) Crude product 8200g.

[0158] Except adding 2160g xylene, 216g of 35% hydrochloric acid aqueous solution, 3360g water, 120g of 28% sodium hydroxide aqueous solution and 3120g water, and using 31...

Embodiment 3

[0164] Except using hydroquinone instead of resorcinol, the same procedure as in Example 1 was carried out to obtain 320 g of white powder.

[0165] The melting point of the obtained white powder is 171-173°C.

[0166] In addition, the chlorine content of the reaction mixture in the first step was 10.6% by weight.

[0167]The composition of the obtained white powder was measured by GPC. As a result, the aromatic diphosphate (I) represented by compound (3) was 96.6 area %, and the phosphorus compound (II) having a hydroxyphenyl group represented by compound (4) was 0.7% by area. Area %, aromatic monophosphate (VI) represented by compound (7) was 2.1 area %, and aromatic triphosphate (VII) represented by compound (9) was 0.6 area % (refer to the following structural formula).

[0168] The obtained results are shown in Table 1 together with the raw materials used.

[0169] Compound (3)

[0170] Compound (4)

[0171] Compound (7)

[0172] Compound (9)

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Abstract

Disclosed is a method for producing aromatic diphosphates that comprises a first process: a process of reacting specific aromatic monohydroxy compounds having sterically hindered groups at the ortho-position with phosphorus oxyhalides in the presence of Lewis acid catalyst and then removing unreacted phosphorus oxyhalide under reduced pressure to obtain specific diaryl phosphorohalidates, and a second process: a process of reacting the reaction product obtained in the aforementioned process with 0.5 moles of specific aromatic dihydroxy compounds with respect to 1 mole of halogen contained in said reaction product in the presence of Lewis acid catalyst to obtain specific aromatic diphosphates.

Description

technical field [0001] The present invention relates to a method for producing an aromatic diphosphate useful as a phosphorus-based flame retardant. More specifically, the present invention relates to a method for producing an aromatic diphosphate that can reduce the generation of by-products that lower the physical properties of phosphorus-based flame retardants without additional purification treatment such as recrystallization using a solvent. . Background technique [0002] In order to impart flame retardancy to a thermoplastic resin or a thermosetting resin, a method of adding a flame retardant is employed when preparing a resin molded article. As the flame retardant, there are inorganic compounds, organic phosphorus compounds, organic halogen compounds, halogen-containing organic phosphorus compounds, and the like. Among these compounds, organohalogen compounds and halogen-containing organophosphorus compounds exert excellent flame-retardant effects. However, these ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/12B01J27/125B01J27/138C07F9/14C07B61/00
CPCC07F9/12B01J27/125B01J27/16B01J27/138C09K21/12
Inventor 平尾清春大槻胜一辻裕志佐藤广树
Owner DIAHACHI CHEMICAL INDUSTRY CO LTD