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Phosphorus-containing hydroquinone derivative, phosphorus-containing flame-retardant epoxy resin, preparation method and application thereof

A technology of hydroquinone and derivatives, which is applied in the field of phosphorus-containing flame-retardant epoxy resin and its preparation, and can solve problems such as reduced heat resistance, high heat release, and the influence of processing effect on the final state dimensional stability.

Inactive Publication Date: 2012-10-03
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, some flame retardants widely used in electrical components, copper-clad laminates for electrical instruments, and sealing materials, such as brominated epoxy resins and antimonides, are being gradually banned due to their harmfulness to the human body
In addition, the glass transition temperature T of the DGEBA epoxy resin system g Between 120 and 130 °C, there are several processes in the printed circuit board (PCB) process that exceed this temperature range, although the process is at T g The time above is shorter, but when the temperature is higher than T g At this time, the molecular motion state of the cured product system begins to change, which will have a certain impact on the processing effect of the product and the final state of the product (such as warpage, dimensional stability, etc.)
In addition, the high density of circuit boards will lead to high heat release during use. It can be seen that the T of the epoxy resin system will be improved. g Heat resistance, such as heat stability, is very important for modification research, especially halogen-free modification, which cannot be at the expense of reducing heat resistance

Method used

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  • Phosphorus-containing hydroquinone derivative, phosphorus-containing flame-retardant epoxy resin, preparation method and application thereof
  • Phosphorus-containing hydroquinone derivative, phosphorus-containing flame-retardant epoxy resin, preparation method and application thereof
  • Phosphorus-containing hydroquinone derivative, phosphorus-containing flame-retardant epoxy resin, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] (1) With N 2 Pass into the reaction flask of device, stirring device, thermometer, condensate pipe, add 20g terephthalaldehyde, 30g p-aminophenol, and dissolve in the mixing of DMSO and ethanol (EtOH) (DMSO:EtOH=1:2 volume ratio) In the solvent, add 0.6g ZnCl 2as a catalyst. The reaction was heated to 80°C, stirred and refluxed for 3 hours, and cooled to room temperature, a large number of yellow crystals precipitated. Suction filtration, washed 3 times with deionized water, placed in a vacuum oven, dried at 75°C for 24 hours, and the product obtained was recrystallized with a mixed solvent of ethanol / DMSO (8:1) to obtain 46g of Phenolic hydroxyl group, imine dihydric phenol substance BP-1 with Schiff base structure on the skeleton. pass 1 H NMR and FT-IR detection methods, the chemical structure of the synthesized compound BP-1 has been relatively clearly characterized, and the results are respectively figure 1 with figure 2 shown.

[0078] (2) Add 31.6g BP-1, ...

Embodiment 2

[0080] (1) With N 2 Pass into the reaction flask of device, stirring device, thermometer, condensate pipe, add 20g terephthalaldehyde, 30g p-aminophenol, and dissolve in the mixing of DMSO and ethanol (EtOH) (DMSO:EtOH=1:2 volume ratio) In the solvent, add 0.6g ZnCl 2 as a catalyst. The reaction was heated to 80°C, stirred and refluxed for 3 hours, and cooled to room temperature, a large number of yellow crystals precipitated. Repeat the operation of Example 1 step (1) to obtain 46g BP-1.

[0081] (2) In another reaction flask equipped with a stirring device, a thermometer, and a condensate pipe, add the BP-145g obtained by the above reaction dissolved in a mixed solvent of ethanol and DMSO (DMSO:EtOH=1:2 volume ratio), heat to 75°C, stir, dissolve, add 0.7g ZnCl 2 as a catalyst. In thru dry N 2 Under the protection of , began to slowly drop 50g diethyl phosphite, and the dropwise addition was completed in 2 hours. Then the temperature was raised to 90°C, and the reacti...

Embodiment 3

[0084] According to the epoxy equivalent value of the epoxy resin, weigh them respectively according to the equimolar stoichiometric ratio (1:1): Group A: 296.8 mg of the imine epoxy resin containing the Schiff base structure on the skeleton obtained in Example 1 Monomer EP-1 and 68.8mg curing agent 4,4'-diaminodiphenylmethane (MDA); B group: phosphorus-containing flame-retardant epoxy monomer EP-2 and 31.7mg obtained in 225.2mg embodiment 2 Curing agent 4,4'-diaminodiphenylmethane (MDA); Group C: 832.1mg common epoxy resin EPON-828 (DGEBA) and 218.2mg curing agent 4,4'-diaminodiphenylmethane (MDA ). Then use the mixed solvent of acetone and chloroform with a volume ratio of 1:10 as the solvent, stir and mix the groups A, B and C respectively, and remove the solvent under vacuum at room temperature. The obtained mixture was cured at a high temperature in a vacuum oven, and the curing conditions were: 2 hours at 160°C, 2 hours at 180°C, 2 hours at 200°C, and 1 hour at 220°C. ...

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Abstract

The invention discloses a phosphorus-containing hydroquinone derivative, a preparation method and the application thereof as well as phosphorus-containing flame-retardant epoxy resin prepared by the phosphorus-containing hydroquinone derivative, a preparation method and the application thereof. The invention comprises the steps of: first, leading double-aldehyde-group compound and hydroxyl-containing primary amine compound or hydroxyl aldehyde-group compound and phenylenediamine compound to have reaction, and obtaining imine dihydric phenol which has phenolichydroxyl at the two ends of a molecule and contains Schiff base structure on the framework; then, leading the obtained imine dihydric phenol and phosphorous acid diester compound containing active P-H bond to have addition reaction, and obtaining the phosphorus-containing hydroquinone derivative which has phenolichydroxyl at the two ends of the molecule; and finally, leading the obtained phosphorus-containing hydroquinone derivative and epoxy chloropropane to have etherification reaction under the base catalysis, and obtaining the phosphorus-containing flame-retardant epoxy resin which has flame retardance, heat resistance andgood comprehensive performance. The experimental result proves that the phosphorus-containing flame-retardant epoxy resin can adapt to the requirement of electronic industry for high-performance highpolymer material.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a phosphorus-containing hydroquinone derivative and its preparation method and application, and a phosphorus-containing flame-retardant epoxy resin prepared from the phosphorus-containing hydroquinone derivative and its preparation method with application. Background technique [0002] In the application of the electronics industry, epoxy resin is widely used in laminate materials for printed circuit boards, plastic packaging materials for integrated circuits and electronic components due to its excellent adhesion, mechanical strength, and electrical insulation. , surface protection materials for printed circuits, and adhesives for flat panel display assembly. According to relevant statistics, in all the fields of thermosetting resin materials for electronics, the epoxy resin system is used in the largest amount, accounting for more than 40%, and has become an extremely importa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/40C08G59/06C08L63/00C07F9/655C09K21/14C09K21/12
Inventor 许凯刘欢陈鸣才苏江勋蔡华伦
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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