Synthesis and Application of a Triazine Derivative Flame Retardant

A technology of triazine derivatives and flame retardant materials, applied in the field of flame retardant material preparation, can solve problems such as application limitation, influence on mechanical properties of materials, human health and environmental hazards, and achieve outstanding flame retardant effect, good carbon-forming performance, The effect of excellent flame retardant properties

Active Publication Date: 2022-02-08
HUNAN INSTITUTE OF ENGINEERING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the flame retardant materials used in textiles mainly include ① organic halogen flame retardant system, ② nitrogen based flame retardant system, ③ phosphorous based flame retardant system, ④ silicon based flame retardant system, etc. Among them, although organic halogen flame retardant materials have excellent flame retardant properties, The amount of addition is small, but when it burns, it will produce a large amount of toxic, harmful and strong irritating gas, causing direct, potential and long-term harm to human health and the environment, thus making the research and development of halogen-free flame-retardant materials an inevitable trend; The main advantages of nitrogen-based, phosphorus-based, and silicon-based flame retardant materials are low toxicity, low smoke, and low corrosion. However, due to the large amount of addition required, the mechanical properties of the material are often affected, so their application is also limited. With the development of social economy, health and environmental protection issues have increasingly become the focus of people's attention, and the green development strategy has become an important national development strategy. As a rising star in modern flame retardants, P-N flame retardants have overcome the traditional The disadvantages of decomposing and releasing toxic gases, combined with the advantages of phosphorus-based flame retardants and nitrogen-based flame retardants, have become a hot spot for current scholars.

Method used

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  • Synthesis and Application of a Triazine Derivative Flame Retardant
  • Synthesis and Application of a Triazine Derivative Flame Retardant
  • Synthesis and Application of a Triazine Derivative Flame Retardant

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Synthesis of 2,4,6-tris(4-formylphenoxy)-1,3,5-triazine (ZJT).

[0043] Weigh 22.00g (0.054mol) of p-hydroxybenzaldehyde and 10.00g (0.18mol) of cyanuric chloride in a 100mL beaker, add 80.00mL of dichloromethane to dissolve, 0~5℃ ice water bath, stir, add 6.00mL of three Ethylamine (TEA) was used as a phase transfer catalyst. Weigh 7.20g of sodium hydroxide and dissolve in 50.00mL of distilled water. Then sodium hydroxide solution was added slowly and stirred for 10 minutes to complete the reaction. The above-mentioned reactants were introduced into a 500 mL three-necked flask, and heated to reflux for two hours. Then dichloromethane was distilled off, filtered, dried, and recrystallized from ethyl acetate. The organic intermediate 2,4,6-tris(4-formylphenoxy)-1,3,5-triazine (ZJT) is obtained. Yield: 95.86%. FTIR (KBr), ν / cm-1: 1161.95, 1214.49 (C-O-Ar), 1569.18, 1501.37, 1376.00 (Ar), 2836.37, 2742.30, 1701.16 (Ar-CHO). 1 H NMR (CDCl3, 300 MHz) δ: 7.31-7.33 (t, 6...

Embodiment 2

[0045] Synthesis of Novel Triazine Derivative Flame Retardant Material NPFR

[0046]Weigh 7.58g (69mmol) of p-aminophenol into 150.00mL of 1,4-dioxane, heat until completely dissolved, then add 9.35g (21mmol) of the intermediate, and heat to reflux for 12h under nitrogen protection. Weigh 14.60 g DOPO (69 mmol) and dissolve it in 60.00 mL 1,4-dioxane, heat until completely dissolved, and the solution becomes colorless and transparent. Then DOPO solvent was slowly added to the above reaction, vacuumed, heated to reflux under nitrogen protection for 12 hours, rotary evaporated, washed with cold ethanol, and dried in a vacuum oven at 60°C for 24 hours. The yield was 94.76%. FTIR(KBr), v / cm -1 : 3317.65 (N-H), 1569.37, 1371.31 (P-Ar), 1213.11 (P=O). 1 H NMR (DMSO-d6, 300MHz) δ: 8.46-8.44 (m, 3H), δ: 8.20-7.02 (m, 36H), δ: 6.54-6.19 (m, 12H), 6: 5.68-5.58 (m, 3H), δ: 5.07-5.01 (m, 3H).

Embodiment 3

[0048] The thermodynamic analysis of embodiment 2 gained novel triazine derivative flame retardant material (NPFR)

[0049] The test conditions of DSC thermodynamic analysis of NPFR are: in N 2 In the atmosphere, the temperature rises from room temperature to 280°C at a rate of 10°C / min, and the TG analysis test conditions are: in N 2 In the atmosphere, the temperature was raised from room temperature to 700°C at a rate of 20°C / min. The DSC and TG analysis results of NPFR were as follows: figure 1 shown. In the DSC curve of NPFR, 189.5°C is the absorption peak when NPFR melts, and the phosphorus-containing DOPO group of NPFR-2 begins to decompose when heated at 261.1°C. As the temperature rises, absorption peaks appear successively at 324.2°C, 349.6°C, 387.1°C, 462.1°C, etc., indicating that other bonds such as triazine ring and benzene ring are broken successively. The TG test results of NPFR are basically consistent with DSC. As the temperature rises, around 260-420°C is ...

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Abstract

The invention discloses the synthesis of a novel triazine derivative flame retardant (NPFR) based on a triazine six-membered heterocyclic ring and phosphaphenanthrene structure and its application on cotton textiles. Its chemical structure name is tri-[4 -(p-Hydroxyaniline-phosphaphenanthrene)methylene-phenoxy]-1,3,5-triazine, abbreviated as NPFR. Its preparation method is: synthesize 2,4,6-three (4-formylphenoxy)-1,3,5-triazine (ZJT) by reaction of cyanuric chloride (TCT) and p-hydroxybenzaldehyde; NPFR was synthesized by the reaction of ZJT, p-aminophenol and 9,10-dihydro-9-oxa-10-phosphinephenanthrene-10-oxide (DOPO). The present invention selects a triazine six-membered heterocyclic ring (N source) with excellent thermal stability as the core, and introduces a DOPO group (P source) with good flame retardant performance, which improves the thermal stability of the flame retardant molecule and Increased flame retardancy through N‑P synergy. When the novel triazine derivative flame retardant NPFR of the present invention is applied to flame retardancy of cotton fabrics, it has higher limiting oxygen index and excellent char formation rate.

Description

technical field [0001] The present invention relates to the technical field of preparation of flame retardant materials, in particular to the preparation of a class of novel triazine derivative flame retardant materials based on cyanuric chloride and DOPO structures and their application in various types of flame retardant substrates, especially Application in cotton textiles. Background technique [0002] With the widespread use of polymers, fire safety is a growing concern. Many safety testing organizations, including Underwriters Laboratories (UL), the International Organization for Standardization (ISO), and the American Society for Testing and Materials (ASTM), have published various standard standards that define the required resistance of polymers in a given classification. flammability. [0003] Most commodity textiles are too flammable. As one of the most commonly used textile raw materials, cotton fiber has a limiting oxygen index of only 18%, which is extremely ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): D06M13/285C07F9/6571D06M101/06
CPCD06M13/285C07F9/657172D06M2101/06D06M2200/30
Inventor 邓继勇符雅芬颜东周鄂潘紫璐姜亚宁
Owner HUNAN INSTITUTE OF ENGINEERING
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