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Method for the production of bridged dibenz [c,e] [1,2] - oxaphosphorin-6-oxides

A technology of phosphaphenanthrene and oxa, which is applied in the field of preparation of bridged 9-oxa-10-phosphaphenanthrene-10-oxide, which can solve the problems that are not suitable for large-scale application

Inactive Publication Date: 2010-02-17
EMS PATENT AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In conclusion, the preparation method described in WO 2006 / 084488A1 is especially unsuitable for large-scale applications

Method used

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  • Method for the production of bridged dibenz [c,e] [1,2] - oxaphosphorin-6-oxides
  • Method for the production of bridged dibenz [c,e] [1,2] - oxaphosphorin-6-oxides
  • Method for the production of bridged dibenz [c,e] [1,2] - oxaphosphorin-6-oxides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Preparation of compound VIII:

[0067]

[0068] In a vacuum-sealed glass apparatus equipped with a sturdy stirrer, thermometer, inert gas supply tube, and heating bath, 32.67 g of anhydrous 1,3,5-tris(2-hydroxyethyl)-isocyanuric acid (THIC )heating. After the THIC had melted, stirring was started and the temperature of the heating bath was lowered to 135°C. Then, 96.5 g of 10-(N(1-propyl)-amino)-9,10-dihydro-9-oxa-10-phosphaphenanthrene Ia preheated to about 120° C. were added. A few minutes after the addition of the reagent, the reactor pressure was carefully depressurized and the reaction mixture started to foam. When foaming ceased, the pressure was further slowly reduced until finally 2-5 mbar was reached. At this point, with continued agitation under the vacuum and at a temperature of 130-135°C, a homogeneous melt was gradually prepared from the two-component mixture. The 1-propylamine obtained during the conversion was condensed in a vacuum trap. use 1 H-...

Embodiment 2

[0070] Preparation of Substance IX:

[0071]

[0072] instrument:

[0073] 1 4-liter 4-neck round bottom flask equipped with the following parts:

[0074] ●Sturdy glass stirrer with vacuum-tight installation;

[0075] ●Internal thermometer;

[0076] ●Inert gas connectors;

[0077] ● Liebig condenser with condensing receiver;

[0078] ● heating bath;

[0079] ●Vacuum pump with vacuum trap.

[0080] In a 4-necked flask filled with argon or nitrogen, add 1131g (4.33mol) 1,3,5-tris(2-hydroxyethyl)-isocyanuric acid (THIC, IVa) and 1.52g p-toluenesulfonate A mixture of acid hydrates, melted and heated to 185°C with stirring. After 3 hours of reaction, the resulting water was distilled off by reducing the pressure to about 50 mbar in about 5 minutes. Next, the inert gas was supplied again and a second portion of p-toluenesulfonic acid hydrate (0.6 g) was added. The melt was then stirred for a further 8 hours at 185°C. Subsequently, the resulting water was removed at ab...

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Abstract

The invention relates to an improved method for the synthesis of monomeric and polymeric nitrogen-bridged derivatives of dibenz[c,e] [1,2]-oxaphosphorin-6-oxides. These substances can be used as flameproofing agents for polyesters, polyamides, polycarbonates, epoxy resins, inter alia polymers.

Description

technical field [0001] The present invention relates to an improved monomer and Method of Polymerizing Nitrogen-Bridged Derivatives. These substances are useful as flame retardants for polyesters, polyamides, polycarbonates, epoxies, and other polymers. Background technique [0002] So far, nitrogen-containing 9-oxa-10-phosphaphenanthrene-10-oxides have been prepared by two methods: [0003] 1. For example, as described in DE 27 30 345, in the presence of primary or secondary amines, by 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (6H-dibenz[ c,e][1,2]-oxaphosphorin-6-oxide) is prepared by aminomethylation with aldehydes or ketones, preferably with formaldehyde. Patent documents (US 4,742,088; JP 2002-284850; JP 2001-323268) also describe the use of these compounds as flame retardants for various polymers. [0004] 2. By conversion of alkoxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxides with nitrogen-containing polyols and subsequent Michaelis-Arbuzov -Arbuz...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6571
CPCC07F9/65719C07F9/6571C09K21/12
Inventor 曼弗雷德·多琳布丽日特·林德纳安德烈亚斯·卡普兰
Owner EMS PATENT AG