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Acid controlled degradation ketal-type alicyclic epoxy resin, preparation method and application

An epoxy resin and cycloaliphatic technology, which is used in the field of acid-controlled degradation of ketal-type cycloaliphatic epoxy resin, preparation and application, can solve the problems of inability to melt microorganisms, degradation, insolubility, etc., and achieve degradation time can be achieved Adjustment, low temperature degradation effect

Inactive Publication Date: 2019-05-14
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional epoxy resins will form a highly cross-linked three-dimensional network structure after cross-linking and curing, which cannot be dissolved, melted, or degraded by microorganisms. Repair, replacement and repair of products using this type of epoxy resin as binder Recycling and other operations have brought great difficulties
During the packaging process, the damage of the chip will lead to the scrapping of the entire component, which reduces the packaging yield of the product. When the scrapped product cannot be repaired, the production cost will be increased and the environment will be polluted.

Method used

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  • Acid controlled degradation ketal-type alicyclic epoxy resin, preparation method and application
  • Acid controlled degradation ketal-type alicyclic epoxy resin, preparation method and application
  • Acid controlled degradation ketal-type alicyclic epoxy resin, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Preparation of bifunctional ketal-based cycloaliphatic epoxy resin:

[0039] (1) Under ice-water bath conditions, add 44.868 grams of 3-cyclohexene-1-methanol, 20 grams of 5A molecular sieves, 1.902 grams of p-toluenesulfonic acid monohydrate, 150 Add 9.814 g of cyclohexanone dropwise to 1 ml of n-hexane, stir and react for 12 hours to terminate the reaction, wash the product with 15% NaO in 1 hour aqueous solution, then wash with deionized water until neutral, dry with anhydrous magnesium sulfate, and filter , concentration, and distillation under reduced pressure to obtain an intermediate product with a yield of 60%.

[0040] (2) 45 grams of potassium persulfate compound salt and 0.06 grams of ethylenediaminetetraacetic acid were dissolved in 240 milliliters of deionized water to prepare an epoxidation reagent solution. Under ice-water bath conditions, in a 1000 ml four-neck flask equipped with a mechanical stirrer, a thermometer, and a constant pressure dropping fun...

Embodiment 2

[0043] Preparation of bifunctional ketal-based cycloaliphatic epoxy resin:

[0044] (1) At -15°C, add 28.043 grams of 3-cyclohexene-1-methanol, 37.5 grams of calcium sulfate, 2.403 grams of methanesulfonic acid, and 375 milliliters of toluene into a 500 milliliter three-necked flask equipped with mechanical stirring and a thermometer. 12.2675 grams of cyclohexanone was added dropwise, and the reaction was terminated after stirring for 24 hours. The product was washed with 15% NaO in an aqueous solution for 24 hours, and then washed with deionized water to neutrality, dried with anhydrous magnesium sulfate, filtered, and concentrated. Distillation under reduced pressure gave an intermediate product.

[0045](2) Dissolving 57.2 grams of m-chloroperoxybenzoic acid in 200 milliliters of dichloromethane was prepared as an epoxidation reagent solution. Under the condition of -25°C, in a 500 ml four-necked bottle equipped with mechanical stirring, a thermometer, and a constant press...

Embodiment 3

[0047] Preparation of bifunctional ketal-based cycloaliphatic epoxy resin:

[0048] (1) Under the condition of 15°C, add 70.106 grams of 3-cyclohexene-1-methanol, 50 grams of copper sulfate, 12.136 grams of sulfamic acid, and 187.5 milliliters of benzene in a 500 milliliter three-necked flask equipped with mechanical stirring and a thermometer. 12.2675 grams of cyclohexanone was added dropwise, and the reaction was terminated after stirring for 48 hours. The product was first washed with 15% NaO aqueous solution for 1 hour, and then washed with deionized water until neutral, dried with anhydrous magnesium sulfate, filtered, concentrated, and decompressed. Distillation gave an intermediate product.

[0049] (2) 72 grams of p-nitroperoxybenzoic acid was dissolved with 200 milliliters of N,N-dimethylformamide to prepare an epoxidation reagent solution. Under the condition of 25°C, add 33.49 g of the intermediate product in a 500 ml four-necked bottle equipped with mechanical sti...

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Abstract

The invention provides acid controlled degradation ketal-type alicyclic epoxy resin, a preparation method and an application, and belongs to the technical field of new materials. The epoxy resin is completely prepared by connecting alicyclic or epoxy group alicyclic through a ketal bond, wherein a chemical structural formula thereof is as shown in the description. The preparation method comprisesthe following steps: adding alicyclic olefin methyl alcohol and an acid catalyst to an organic solvent, in a temperature of -15 to 15 DEG C, adding cyclohexyl ketone and a moisture scavenger, continuously reacting for 12-48 hours, to obtain an intermediate; in a temperature of -25 to 25 DEG C, dropwise adding epoxidation reagent solution and alkali liquor to intermediate solution, controlling a PHof a reaction system to be 7-8, reacting for 6-24 hours, to obtain a product. The obtained epoxy resin is a liquid state with lower viscosity in a room temperature. A product after acid anhydride curing is degradable in acid, and a degradation speed is controllable along with an intensity change of the acid. The provided epoxy resin serving as an adhesion agent is used for the electronic packaging or carbon fiber composite material field, and recycling precious materials of precious metal or carbon fibers and the like.

Description

technical field [0001] The present invention relates to a ketal-type liquid cycloaliphatic epoxy resin, a preparation method and its application, in particular to a difunctional ketal-type cycloaliphatic epoxy resin that is liquid at room temperature and can be degraded under acid control, a preparation method and The invention is used for packaging materials of integrated circuits, light-emitting diodes (LEDs) optoelectronic devices or used for carbon fiber / epoxy resin composite matrix resin materials, and belongs to the technical field of new materials. Background technique [0002] Alicyclic epoxy resin has a high glass transition temperature, low viscosity and good UV resistance, and is widely used in coatings, high-voltage insulating materials, thinners, electronic components and printed circuit board coatings, etc. field. Traditional epoxy resins will form a highly cross-linked three-dimensional network structure after cross-linking and curing, which cannot be dissolv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G59/24C07D301/14C07D303/30
Inventor 王忠刚丁昇征
Owner DALIAN UNIV OF TECH
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