Organophosphorus compound and flame retardant agent comprising same, and method for producing organophosphorus compound

A manufacturing method and compound technology, applied in the field of organophosphorus compounds, can solve the problems of unfavorable implementation, low solubility, unfavorable economy, etc., and achieve the effect of high heat resistance

Inactive Publication Date: 2018-09-28
MARUZEN PETROCHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0021] However, the conventional method of reacting DOPO with dihalogenated ethane or ethylene glycol requires a step of removing catalysts, halogen compounds, etc., which is disadvantageous from an economic point of view.
In particular, organophosphorus compounds containing two DOPO structures are usually crystalline solids with low solubility in solvents, so simple purification methods such as distillation or recrystallization cannot be applied, and they need to be repeatedly performed exclusively with water or organic solvents Slurry washing
Therefore, a large amount of waste liquid will be produced, which is extremely unfavorable for industrial implementation
[0022] In addition, in the addition reaction of P(O)-H bonds and carbon-carbon unsaturated bonds, a catalyst or catalyst residue removal process is also required, which is extremely unfavorable for industrial implementation.

Method used

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  • Organophosphorus compound and flame retardant agent comprising same, and method for producing organophosphorus compound
  • Organophosphorus compound and flame retardant agent comprising same, and method for producing organophosphorus compound
  • Organophosphorus compound and flame retardant agent comprising same, and method for producing organophosphorus compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0145] Embodiment 1: Synthetic example (1) of organophosphorus compound

[0146] The following organophosphorus compound (P1) was synthesized by the following reaction.

[0147] [chemical formula 14]

[0148]

[0149] A flask with a capacity of 300 mL was prepared, and 50.0 g of DOPO was charged into the container to perform nitrogen substitution. 94.5 g of dimethyl vinylphosphonic acid (DMVP) was put into this container, and it reacted maintaining the temperature in the system at 130 degreeC (DOPO / DMVP=25 / 75 by molar ratio). After 8 hours from charging vinylphosphonic acid dimethyl, it was made to cool, and 96.3 g of toluene was added to the reaction liquid, and the product was deposited. The precipitated product was separated and recovered by filtration, and dried under reduced pressure to obtain 45.35 g of a white solid (99.38% yield). The resulting solid had a melting point of 138°C. In addition, formation of the compound (P1) was confirmed by 1H-NMR measurement of...

Embodiment 2

[0150] Embodiment 2: the synthesis example (2) of organophosphorus compound

[0151] The following organophosphorus compound (P2) was synthesized by the following reaction.

[0152] [chemical formula 15]

[0153]

[0154] A flask with a capacity of 500 mL was prepared, 120.0 g of DOPO was charged into the container, and nitrogen substitution was performed. 291.3 g of vinylphosphonic acid diphenyl ester (DPVP) was put into this container, and it reacted maintaining the temperature in the system at 130 degreeC (DOPO / DPVP=33 / 67 by molar ratio). After 8 hours from the injection of the vinylphosphonic acid diphenyl ester, it was allowed to cool, and the reaction liquid was injected into 1 L of acetone to deposit the product. The precipitated product was separated and recovered by filtration, and dried under reduced pressure to obtain 65.30 g of a white solid (yield 62.67%). The resulting solid had a melting point of 145°C. In addition, formation of the compound (P2) was co...

Embodiment 3

[0155] Embodiment 3: the synthesis example (3) of organophosphorus compound

[0156] Charge DOPO 0.25g, 9,10-dihydro-9-oxa-10-vinyl-10-phosphaphenanthrene-10-oxide (DOVP) 0.28g in the kugelrohr still (in terms of molar ratio DOPO / DOVP=50 / 50), decompressed to 10kPa, and heated at 200°C for 3 hours. Next, the temperature was raised to 230° C., followed by further heating for 1 hour, and unreacted DOVP was distilled off from the top of the still. Methanol was added to the bottom of the still, and the product was washed, separated by filtration, and dried under reduced pressure to obtain 0.48 g of a white solid (90% yield). The white solid was analyzed by 1H-NMR, and it was confirmed that it was the target 6,6'-(1,2-ethanediyl)bis[6H-dibenzo[c,e][1,2]oxaphosphapine Hexylcyclo-6-oxide] (EBDOPO).

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Abstract

The present invention addresses the problem of providing: a novel organophosphorus compound which can impart flame retardancy to an amorphous resin without deteriorating the heat resistance and transparency of the amorphous resin even when added to the amorphous resin in a smaller amount, and which can be used for wide varieties of resins; a flame retardant agent comprising the organophosphorus compound; and a method for producing an organophosphorus compound. An organophosphorus compound represented by general formula (1) (wherein R1 and R2 independently represent a hydrogen atom, an alkyl group having 1 to 15 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 15 carbon atoms, or an alkylaryl group having 7 to 15 carbon atoms; R3 and R4 independently represent an alkyl group having 1 to 15 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 15 carbon atoms, an alkylaryl group having 7 to 15 carbon atoms, an alkoxy group having 1 to 15 carbon atoms, an aryloxy group having 6 to 12 carbon atoms, an aralkyloxy group having 7 to 15 carbon atoms, or an alkylaryloxy group having 7 to 15 carbon atoms, provided that R3 and R4 may be bound to each other to form a ring; and m and n independently represent 1, 2, 3 or 4).

Description

technical field [0001] The present invention relates to an organophosphorus compound, a flame retardant containing the same, and a method for producing the organophosphorus compound. Background technique [0002] Conventionally, halogen-based flame retardants have been widely used as representative flame retardants for flame retardants used in thermoplastic resins. However, since halogen-based flame retardants generate toxic gas depending on incineration conditions, the use of halogen-based flame retardants has been limited in recent years from the viewpoint of the environment and safety. [0003] Therefore, phosphorus-based flame retardants are widely used as flame retardants considered to be more environmentally friendly than halogen-based flame retardants. Phosphate-based flame retardants such as bisphenol A condensed phosphoric acid diphenyl ester and resorcinol condensed phosphoric acid di(xylyl) ester are known as phosphorus-based flame retardants. [0004] However, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6574C08K5/5397C08L101/00C09K21/12
CPCC07F9/657172C07F9/65719C08K5/5397C08L101/00C09K21/12C07F9/65744C08L2201/02C08K5/5313
Inventor 山崎忠饭塚彻也高桥孝木南悠横尾雄友
Owner MARUZEN PETROCHEMICAL CO LTD
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