Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Cyclopentadienyl iron salt flame retardant containing phosphorus and nitrogen elements, and preparation method and application thereof

A technology of nitrogen element and ferrocene salt, which is applied to functional metallocene compounds and their application fields, can solve the problems of affecting resin properties and residues, and achieve the effects of good flame retardant effect, small addition amount, and simple and convenient operation.

Active Publication Date: 2016-02-03
BEIJING UNIV OF CHEM TECH
View PDF4 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

During the initiation process of ferrocene salts with a simple ligand structure, the removed ligands will remain in the resin and affect the performance of the resin. One of the directions to solve this problem is to endow the aromatic hydrocarbon ligands in ferrocene salts with synergistic properties with ferrocene. functionality, but there are few reports on this direction

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Cyclopentadienyl iron salt flame retardant containing phosphorus and nitrogen elements, and preparation method and application thereof
  • Cyclopentadienyl iron salt flame retardant containing phosphorus and nitrogen elements, and preparation method and application thereof
  • Cyclopentadienyl iron salt flame retardant containing phosphorus and nitrogen elements, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1 flame retardant ( n 6 -4-(N-(1-p-hydroxyphenyl-1-DOPO)methyl)aminophenoxybenzene)( n 5 -Synthesis of iron hexafluorophosphate FCOPH

[0038] The synthesis process is shown in the following formula:

[0039]

[0040] In a 250ml round bottom flask add ( n 6 -chlorobenzene)( η5 -Cyclopentadiene) iron hexafluorophosphate (Fc-Cl) 20g (0.026mol), 4-aminophenol 7g (0.032mol), potassium carbonate 10g (0.036mmol), N,N-dimethylformamide 120ml , react in the dark at room temperature (25°C), and monitor the reaction with a thin-layer chromatography spot plate until ( n 6 -chlorobenzene)( n 5 -cyclopentadiene) iron hexafluorophosphate reacts completely. The reactant was poured into cold water, a yellow solid was precipitated, left to stand, filtered under reduced pressure, and the filter cake was rinsed with ethanol three times to obtain the target compound ( n 6 -aminodiphenyl ether) ( n 5 -cyclopentadiene) iron hexafluorophosphate, yellow sol...

Embodiment 2

[0043] Embodiment 2 flame retardant ( n 6 -4-(N-(1-phenyl-1-DOPO)methyl)aminophenoxybenzene)( n 5 -Synthesis of iron hexafluorophosphate (FCOP)

[0044] The synthesis process is shown in the following formula:

[0045]

[0046] Add ( n 6 – aminodiphenyl ether) ( n 5 -Cyclopentadiene)iron hexafluorophosphate (Fc-NH 2 ) 20g (0.044mol), benzaldehyde 4.7g (0.044mol) and 100ml DMF, protected from light, stirred at 30°C for 5 hours, then added 9.6g (0.044mol) DOPO, monitored the reaction by TLC, and the reaction was completed after 13 hours . After the reaction was completed, the reaction solution was poured into cold water, a yellow solid was precipitated, left standing, and filtered to obtain the target product (yield: 82%).

[0047] (KBr) νmax (cm?1): 842 (PF 6 - ), 929 (P-O-C), 1237 (P=O), 1456, 1477, 1503, 1607 (Arring), 3090, (Ar-H); 1 H-NMR (400MHz, DMSO- d 6 ) δ: 5.08 (s, 5H, CP-H), 5.15 (m, 1H, P-C-H), 6.10 (m, 3H, Ar-H), 6.25 (t, 2H, Ar-H), 6.65 (m, 1...

Embodiment 3

[0048] Embodiment 3 flame retardant ( n 6 -4-(1-(4-Hydroxyanilino)-1-DOPO)methylbiphenyl) ( n 5 -Synthesis of iron hexafluorophosphate (FCPH)

[0049] The synthesis process is shown in the following formula:

[0050]

[0051] Add 50g (0.13mol) ( n 6 -chlorobenzene)( n 5 -cyclopentadiene) iron hexafluorophosphate, 22.5g (0.15mol) 4-formyl phenylboronic acid, 2mol? L￣ 1 Potassium carbonate aqueous solution 100ml, tetrahydrofuran 200ml, tetrakistriphenylphosphine palladium 0.3g, under the protection of nitrogen, heated to reflux under the condition of avoiding light. The reaction was monitored by thin-layer chromatography, and the reaction was completed within 12 hours. After cooling, filter to remove insoluble impurities, wash the organic phase three times with water, keep the organic phase, concentrate, add methyl tert-butyl ether to the concentrated solvent, a large amount of yellow solids are precipitated, filter to obtain the product, ( n 6 –4-Formyl biphe...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
thermal decomposition temperatureaaaaaaaaaa
thermal decomposition temperatureaaaaaaaaaa
Login to View More

Abstract

The invention discloses a cyclopentadienyl iron salt flame retardant containing phosphorus and nitrogen elements. The flame retardant has a structural general formula as shown in the description. The invention also discloses a preparation method of the cyclopentadienyl iron salt flame retardant containing phosphorus and nitrogen elements, and an application of the flame retardant when the flame retardant is added into a light-cured epoxy resin system. The cyclopentadienyl iron salt flame retardant preparation process is simple. According to the preparation process, a cyclopentadienyl iron salt containing a chlorobenzene ligand is adopted as a raw material; an imine intermediate is synthesized, such that a group containing the nitrogen element is introduced; the intermediate is subjected to a reaction with 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, such that a phosphorus-containing flame-retarding group is introduced. With the cyclopentadienyl iron salt provided by the invention, the mobility of the aromatic hydrocarbon ligand removed during a photo-initiation process with the cyclopentadienyl iron salt as an initiator is solved. As an additive flame retardant, cyclopentadienyl iron metal and the ligand containing phosphorous and nitrogen elements provide synergistic flame-retarding effects. Resin added with the compound has a substantially improved flame-retarding property and increased residual char content.

Description

technical field [0001] The invention belongs to the technical field of functional metallocene compounds and their applications, and in particular relates to a class of ferrocene salts containing phosphorus and nitrogen elements, a preparation method thereof, and an application as a flame retardant for epoxy resins. Background technique [0002] Polymer materials are more and more widely used in daily life. However, the potential fire hazard of polymer materials cannot be ignored. Flame retardants can hinder flame combustion and reduce the generation of toxic gases and smoke. Although halogenated flame retardants have good flame retardant effects, they are gradually restricted in use due to high temperature decomposition and generation of toxic and corrosive gases such as hydrogen halides. Organic phosphorus-containing flame retardants have excellent flame retardant effects, are environmentally friendly and non-polluting, and are ideal choices for replacing halogenated flam...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C08K5/00C07F17/02C08L63/10C08L63/00C08L33/04
Inventor 王涛晁鹏杰赵洁
Owner BEIJING UNIV OF CHEM TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com