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Phosphamide compound with flame retardance and preparation method and application thereof to epoxy resin

A compound, the technology of diphenylphosphoramide, applied in the field of flame retardants, can solve the problems of life and property safety threats, large heat release from smoke, fast burning speed, etc., and achieves easy operation, high yield and good thermal performance. Effect

Active Publication Date: 2012-06-20
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most polymer materials are flammable, and the burning speed is fast, and the heat generated by the smoke is large, which poses a huge threat to people's lives and property safety.

Method used

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  • Phosphamide compound with flame retardance and preparation method and application thereof to epoxy resin
  • Phosphamide compound with flame retardance and preparation method and application thereof to epoxy resin
  • Phosphamide compound with flame retardance and preparation method and application thereof to epoxy resin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Preparation of intermediate M1:

[0029] Add 31.5g (0.3mol) of 4-aminophenol, 80.55g (0.3mol) of diphenyl chlorophosphate, catalytic amount (5%) of HOAt, and 200mL of toluene to a 500mL three-necked flask in sequence. 33 mL (0.36 mol) of tetrahydropyridine was added dropwise, and the addition was completed in 30 to 50 minutes. After reacting at 0-40°C for 8 hours, raise the temperature to 50-60°C and continue the reaction for 1-2 hours. After stopping the reaction, filter with suction, wash with water, and recrystallize with acetone:water=2:1 (V / V) to obtain 80.0 g of gray solid, the yield 79%, melting point 184-186°C.

Embodiment 2

[0031] Preparation of Compound I-1

[0032] In a 100mL three-neck flask equipped with a thermometer, a constant pressure dropping funnel and a reflux condenser, add 40mmol of the intermediate M140mmol, 0.2g of DMAP, 80mmol of pyridine, and 30mL of tetrahydrofuran, stir in an ice bath, control the temperature at -10 to 5°C, and add dropwise 10mL tetrahydrofuran solution dissolved with 20mmol of phenylphosphoryl dichloride, after adding, react at 5°C for 5h, heat up and reflux, stop the reaction after 1h, let stand and cool overnight, a white solid precipitates, filter with suction, DMF:H 2 O=4:1 (V / V) recrystallized to give a white solid with a yield of 87% and a melting point of 173-175°C.

[0033] 1 H NMR (600MHz DMSO-d 6 )δ(ppm): 7.11~7.14(t, 8H, Ph-H), 7.19~7.22(m, 12H, Ph-H), 7.37~7.40(t, 8H, Ph-H), 7.59~7.61(t , 2H, Ph-H), 7.71(s, 1H, Ph-H), 7.88~7.91(s, 2H, Ph-H), 8.14~8.86~8.88(d, 2H, N-H); 31 P NMR (400MHz) δ (ppm): -7.04 (s, O P (O)N), 12.15 (s, O P (O)C);IR(KBr...

Embodiment 3

[0035] Preparation of Compound I-2

[0036] In a 100mL three-necked flask, add intermediate M140mmol, NHPt 0.15g, spirophosphoryl chloride (Md) 30mmol, 1,2-dichloroethane 50mL, add triethylamine 80mmol dropwise at -15~10°C, and complete the addition , kept at 20-40°C for 3h, then raised the temperature to reflux, kept at reflux for 10h, stopped the reaction, let it stand for cooling, and then went through silica gel column chromatography to obtain a white solid with a yield of 65% and a melting point of 102-105°C.

[0037] 1 H NMR (600MHz CDCl 3 -d) δ (ppm): 4.14 ~ 4.20 (m, 2H, CH 2 O ), 4.25~4.28(m, 2H, CH 2O ), 4.51~4.53(t, 2H, CH 2 O ), 4.79~4.84(m, 2H, CH 2 O ), 6.74~6.75(d, 2H, N-H), 7.10~7.18(m, 20H, Ph-H), 7.27~7.30(m, 8H, Ph-H); 31 P NMR (400MHz) δ (ppm): -7.10 (s, O P (O)N), -13.54 (s, O P (O)O);IR(KBr)υ(cm -1 ): 3443(N-H), 3133(Ph-H), 2970(CCH 2 -H), 1638, 1570, 1509 (Ph-C), 1458 (CH 2 -H), 1262(P=O), 1139(P-N), 1122, 1070((P)-O-C), 995, 954(P(O...

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Abstract

The invention discloses a phosphamide compound with flame retardance and a preparation method and application thereof to epoxy resin. The phosphamide compound is the O, O'-diphenyl phosphamide ester derivative which has the general formula I, contains two flame retardant elements which are phosphorus and nitrogen and can generate the intramolecular synergistic flame retardance effect. The phosphamide compound can be used as the active ingredients of the flame retardant, can be added into epoxy resin as the flame retardant to produce the flame-retardant epoxy resin material and can be also compounded with melamine (MA) so as to be applied to the epoxy resin material. The phosphamide compound can significantly improve the flame retarding function of the epoxy resin material.

Description

technical field [0001] The invention relates to a preparation method and application of a class of phosphoramide compounds containing phenylphosphonate, belonging to the technical field of flame retardants. It specifically relates to a phenylphosphonate-containing phosphoramide compound with flame retardancy, its preparation and application in epoxy resin. Background technique [0002] Various organic polymer materials, such as epoxy resin (EP) and other various copolymers, have a wide range of uses in daily production and life, and have a tendency to gradually replace traditional materials. However, most polymer materials are flammable, and the burning speed is fast, and the heat generated by the smoke is large, which poses a huge threat to people's lives and property safety. Therefore, it is of great significance to modify the flame retardant of polymer materials. [0003] In the flame retardant system of polymer materials, the synergistic use of two or more flame retard...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/40C07F9/6574C07F9/24C08L63/00C08K5/5399C08K5/3492
Inventor 贺红武张宏张翔宇
Owner HUAZHONG NORMAL UNIV
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