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Preparation method of novel high nitrogen content compounds containing phosphaphenanthrene and phosphazene double-effect functional group

A compound and functionalization technology, applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc., can solve the problems of no reports of phosphazenes and phosphaphenanthrenes with double-effect functional groups, and achieve The reaction system is green and environmentally friendly, the content of benzene ring is high, and the effect of mild reaction conditions

Inactive Publication Date: 2013-12-11
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, this type of phosphazene and phosphaphenanthrene dual-effect functional group compound obtained by this process has not been reported at home and abroad.

Method used

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  • Preparation method of novel high nitrogen content compounds containing phosphaphenanthrene and phosphazene double-effect functional group
  • Preparation method of novel high nitrogen content compounds containing phosphaphenanthrene and phosphazene double-effect functional group
  • Preparation method of novel high nitrogen content compounds containing phosphaphenanthrene and phosphazene double-effect functional group

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0030] 6g DOPO, 2g hexaaminophenoxycyclotriphosphazene, 2g CCl 4 Dissolve in 100ml of methanol, heat to 80°C, and react for 10 hours; after the reaction is completed, cool the reaction to room temperature, filter the product with a Buchner funnel to obtain a yellow powder, add 50ml of acetone to wash 3 times, and obtain a light yellow powder. Dry in a vacuum oven to finally obtain product 2a, whose structural formula is as follows figure 1 Product 2, the product is 4.98g of powder, the yield is 96%, and the purity is 99.2%. 1 H NMR (DMSO-d6, TMS, ppm): 8.75 (br, 1H; NH), 31 P NMR (DMSO-d6, ppm): 8.0 (P-O), 8.9 (P=N)

example 2

[0032] Dissolve 1.2g of hexaaminophenoxycyclotriphosphazene, 0.46g of formaldehyde solution and 2g of DOPO in 50ml of methanol, heat to 50°C, add 1g of AlCl after 1 hour of reaction 3 After the reaction is completed, the reaction is cooled to room temperature, and the product is filtered with a Buchner funnel to obtain a light yellow powder, and 50 ml of acetone is added to wash 3 times to obtain a white powder. when figure 2 When the R group in product 3 is H, the product is 2.99g of powder, the yield is 92%, and its nitrogen content is 5.86%. 1HNMR (DMSO-d6, TMS, ppm): 5.70 (s, 1H, NH), 4.02, 3.85 (m, 2H, CH 2 ), 31 P NMR (DMSO-d6, ppm): 32.11 (P-O), 9.75 (P=N)

example 3

[0034] Dissolve 2.4g of hexaaminophenoxycyclotriphosphazene, 1.2g of formaldehyde solution and 5g of DOPO in 100ml of acetone, heat to 90°C, and react for 10 hours; after the reaction is completed, the reaction is cooled to room temperature, and the product is filtered with a Buchner funnel to obtain Pale yellow powder, add 50ml of methanol and wash 3 times to obtain white powder, dry the product in a vacuum oven at 80°C, and finally obtain product 3a, whose structural formula is figure 2 When the R group in product 3 is H, the product is 6.1 g of powder, the yield is 94%, and its nitrogen content is 5.86%. 1H NMR (DMSO-d6, TMS, ppm): 5.70 (s, 1H, NH), 4.02, 3.85 (m, 2H, CH 2 ).

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Abstract

The invention belongs to the field of organic synthesis chemistry, and relates to a preparation method of a class of novel compounds containing a phosphaphenanthrene and phosphazene double-effect functional group. The compound is characterized in that the compound has a branched structure adopting cyclotriphosphazene as an inner core and adopting 9,10-dihydro-9-oxa-phosphaphenanthrene-10-oxide (short for DOPO) as a side group, wherein the structural formula is represented by the figure 1. According to the present invention, hexa(4-amino-phenoxy)-cyclotriphosphazene and 9,10-dihydro-9-oxa-phosphaphenanthrene-10-oxide (short for DOPO) are subjected to a Aterton-Todd reaction and a Kabachnik-Fields addition reaction to obtain a class of novel compounds containing the phosphaphenanthrene and phosphazene double-effect functional group. The compounds have the following advantages that: characteristics that the compounds contain phosphorus and nitrogen, do not contain halogen, and have substantially increased nitrogen content compared with the double-effect functional group compounds in the prior art are completely utilized, the phosphorus and nitrogen synergistic effect is completely provided, and the compounds can be used in polymer materials so as to achieve expected effects of high fire retardation efficiency and less toxicity.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and in particular relates to a preparation method of a novel double-effect functional group compound containing phosphaphenanthrene and phosphazene with higher nitrogen content. Background technique [0002] 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO for short) has been prepared since the 1970s, but has not been well applied. Until 1998, Taiwan scholar Wang Chunshan and others studied the application of DOPO derivatives in various polyesters and epoxy resins, and obtained excellent flame-retardant polyesters and epoxy resins, which triggered the introduction of phosphophenanthrene groups. Introduced into the research boom of polymers as flame retardant materials. As a phosphorus-containing heterophenanthrene compound, DOPO has the characteristics of non-coplanarity, interaction with intramolecular or intermolecular groups, large volume structure, and certain mol...

Claims

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Application Information

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IPC IPC(8): C07F9/6593C08K5/5399
Inventor 张胜姜鹏谷晓昱扈中武吴申德
Owner BEIJING UNIV OF CHEM TECH
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