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Alicyclic dianhydride compound containing perhydronaphthalene structure as well as preparation method and application thereof

An alicyclic dianhydride and compound technology, applied in the field of functional polymer materials, can solve the problems of high melting point and deep color of polyimide film.

Active Publication Date: 2018-11-23
威海新元科盛新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the tetrahydronaphthalene (tetrahydronaphthalene or tetralin) structure in this type of alicyclic dianhydride monomer molecule still contains aromatic benzene ring units, causing the prepared polyimide film to have a darker color.
At the same time, this type of alicyclic dianhydride has a high melting point (≥200°C), and there are many problems when it is applied to epoxy curing.

Method used

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  • Alicyclic dianhydride compound containing perhydronaphthalene structure as well as preparation method and application thereof
  • Alicyclic dianhydride compound containing perhydronaphthalene structure as well as preparation method and application thereof
  • Alicyclic dianhydride compound containing perhydronaphthalene structure as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] 3,4-Dicarboxy-1,2,3,4-tetrahydro-1-naphthalene succinic dianhydride (TDA)

[0068] Add 250 g (2.55 mol) of maleic anhydride into a 250 mL three-necked flask equipped with a mechanical stirrer, a thermometer, and a gas inlet, and raise the temperature to blow nitrogen. Add 0.65 g of 2,5-di-tert-butylhydroquinone as a polymerization inhibitor after all the solution is dissolved. 398.1 g (3.82 mol) of styrene was added in one portion. Change the nitrogen gas to nitrogen monoxide gas, raise the temperature to 115°C for reaction, and a precipitate appears after 1 hour. After reacting for 5 hours, the temperature was lowered to 60° C., 180 ml of acetonitrile was added, and the mixture was refluxed for 0.5 hours. Cool down slightly, add 200 mL of toluene, and cool. A large number of crystals were precipitated, filtered and washed three times with toluene to obtain loose white crystals with a yield of 90%.

[0069] The structure detection data of this compound are as follow...

Embodiment 2

[0076] 3,4-dicarboxy-1,2,3,4-decalin-1-succinic anhydride (HTDA)

[0077] (1) TDA esterification

[0078] Add 100g of TDA, 192g of methanol and 15.2g of sulfuric acid into a 500ml three-necked flask equipped with a mechanical stirrer and a thermometer, heat up and reflux for 26 hours, cool down after the reaction, and add 300ml of toluene and 300ml of water for extraction after the reaction is completed, and separate the toluene layer , washed with 10% sodium carbonate solution, until the pH value of the aqueous layer is the same as that of the sodium carbonate solution when detected with pH test paper, then washed with water until neutral. Evaporate the toluene to obtain a water-white oil, add an equal amount of methanol, heat up to completely dissolve, then cool down to 30°C and stir to crystallize. After 3 hours of solid precipitation, filter to obtain white crystal TDA tetramethyl ester with a yield of 92%.

[0079] (2) TDA tetramethyl ester hydrogenation

[0080] The hydr...

Embodiment 3

[0092] Preparation of polyimide from HTDA and 4,4'-diaminodiphenyl ether (ODA)

[0093] In a 500 mL three-necked flask equipped with a nitrogen inlet, 2.0024 g (10 mmol) of ODA and 10 g of N-methylpyrrolidone (NMP) were added. After stirring at room temperature to dissolve it completely, add 3.0631g (10mmol) HTDA and 5.2g NMP, adjust the solid content to 25% (weight percentage), continue stirring at room temperature for 24h, add 5.1g (50mmol) acetic anhydride and 3.2 g (40mmol) pyridine, continue stirring at room temperature for 24h. The resulting colorless viscous solution was poured into 150 mL of ethanol to obtain a white filamentous solid. The solid was collected, washed three times with ethanol, and then dried in a vacuum oven at 80°C. Weigh 3 g of solid, add 12 g of NMP, and filter to obtain a polyimide solution with a solid content of 20% (percentage by weight) after the solid is completely dissolved. The polymer solution was coated on a glass plate and heated accord...

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Abstract

The invention discloses a novel alicyclic dianhydride compound containing a decahydronaphthalene structure and polyimides prepared from the alicyclic dianhydride compound. The general molecular formula of the alicyclic dianhydride compound is as shown in the figure (I) in the specification. The alicyclic dianhydride compound can be prepared through the synthetic steps as shown in the figure (II) in the specification. The invention further discloses a colorless and transparent polyimide film prepared from the alicyclic dianhydride compound with the general molecular formula as shown in the figure (I) in the specification. The general molecular formula of the polyimides is as shown in the figure (III) in the specification. The polymer can be prepared by adopting the alicyclic dianhydride compound with the general molecular formula as shown in the figure (I) in the specification and a commercial diamine compound as raw materials and through a two-step thermal imidization, chemical imide and one-step high-temperature solution polycondensation method. The film prepared from polyimide resin has the characteristics of being colorless, transparent, high in glass-transition temperature, lowin dielectric constant and dielectric loss and capable of being used as a film material or a coating material to be applied to the fields of integrated circuits, optical fiber communication, solar batteries and the like.

Description

technical field [0001] The invention belongs to the field of functional polymer materials, and relates to an alicyclic dianhydride monomer compound containing a perhydronaphthalene structure and a preparation method and application thereof. Background technique [0002] In recent years, high-performance polymer materials containing alicyclic structures, including alicyclic polyimides (alicyclic polyimdes), alicyclic epoxy resins (alicyclic epoxy), alicyclic polycarbonate (alicyclic polycarbonate), etc., have been used in optoelectronic devices It has received extensive attention in the field (Hasegawa M. Development of solution-processable, optically transparent polyimides with ultra-low linear coefficients of thermal expansion, Polymers, 2017, 9, 520.). On the other hand, alicyclic structure-containing monomers and curing agents related to high-performance photopolymers have also received extensive attention in recent years. For example, alicyclic dianhydride monomers and ...

Claims

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Application Information

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IPC IPC(8): C07D307/92C08G73/10
CPCC07D307/92C08G73/1007C08G73/1071
Inventor 李璐原伟涛郭田东王金青张健李霄武晓邵军强
Owner 威海新元科盛新材料有限公司
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