Dianhydride monomer containing photocrosslinkable phenyl vinyl ketone element and preparation method thereof

A technology for cross-linking phenyl vinyl ketone and phenyl vinyl ketone, applied in the direction of organic chemistry, etc., can solve problems such as complex synthesis, and achieve the effects of high purity, simple control of synthesis process conditions, and simple raw materials

Inactive Publication Date: 2010-11-24
TSINGHUA UNIV
View PDF0 Cites 10 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Generally, polyimide is obtained by condensation of diamine and dianhydride, and diamine monomers containing chalcone have been reported, but such dianhydride monomers have not been reported due to their complex synthesis.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Dianhydride monomer containing photocrosslinkable phenyl vinyl ketone element and preparation method thereof
  • Dianhydride monomer containing photocrosslinkable phenyl vinyl ketone element and preparation method thereof
  • Dianhydride monomer containing photocrosslinkable phenyl vinyl ketone element and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0045] A preparation method for a dianhydride monomer containing photocrosslinkable phenyl vinyl ketone units, comprising the following steps:

[0046](2-1) Condensation reaction of aromatic aldehyde and ketone to synthesize dihydroxyphenyl vinyl ketone with two phenolic hydroxyl groups: the molar ratio of aromatic aldehyde to ketone is: aromatic aldehyde: ketone = 1 ~ 1.1: 1 or 2 ~2.2:1, the reaction temperature is 0~10℃, the reaction time is 8~16 hours, then add dilute hydrochloric acid to neutralize to pH=5~7, produce precipitate, filter, wash, and dry at 70~100℃ for 6~15 hours Hour, recrystallization, obtain the dihydroxyphenyl vinyl ketone with two phenolic hydroxyl groups;

[0047] (2-2) Synthesis of dihydroxyalkylphenyl vinyl ketone ether with two alcoholic hydroxyl groups: the above-mentioned dihydroxyphenyl vinyl ketone with two phenolic hydroxyl groups is dissolved in a solvent, and the solvent is dimethyl sulfoxide Or N, N-dimethylformamide, made into a homogeneous...

Embodiment 1

[0052] (1-1) Synthetic phenyl vinyl ketone with two phenolic hydroxyl groups:

[0053] Weigh 0.11mol of p-hydroxybenzaldehyde and 0.1mol of p-hydroxyacetophenone into a 250mL single-mouth bottle, add 50mL of ethanol to dissolve, and place in an ice-water bath; weigh 33g of NaOH solid, slowly dissolve it in 33mL of water, and make a concentration It is a 50% NaOH solution, cooled to about 0°C; under constant stirring, slowly add the concentrated alkali solution dropwise to the ethanol solution of aldehydes and ketones. After the dropwise addition, continue to react at below 10°C for 12 hours, neutralize with 1mol / L dilute hydrochloric acid until the pH is around 5, filter, wash with water, and dry at 75°C for 8 hours, then recrystallize with water to obtain a light yellow filament Solid, yield 50%.

[0054] (1-2) synthesis of 1,2,4-benzenetriacid anhydride acid chloride:

[0055] Weigh 38.4g of trimellitic anhydride into a 100mL single-necked bottle, add 50mL of thionyl chlor...

Embodiment 2

[0060] (2-1) Synthesis of phenyl vinyl ketone with two phenolic hydroxyl groups: similar to the step (1-1) of Example 1, except that p-hydroxybenzaldehyde was replaced by m-hydroxybenzaldehyde, the yield was 68%.

[0061] (2-2). Synthesis of 1,2,4-trimellitic anhydride acid chloride: the same as the step (1-2) of Example 1.

[0062] (2-3) Synthesis of a dianhydride monomer containing phenyl vinyl ketone: similar to the step (1-3) of Example 1, except that the 4,4'-dihydroxyl compound synthesized in the step (1-1) is Alone is replaced by the product synthesized in step (2-1), yield 60%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention provides dianhydride monomer containing photocrosslinkable phenyl vinyl ketone element and a preparation method thereof, belonging to the technical field of a macromolecule material. The middle of the monomer structural formula contains the phenyl vinyl ketone element which can generate photocrosslinking reaction under UV-irradiation, two sides of the phenyl vinyl ketone element do not contain or contain 2-6 -CH2- linear-chain flexible chains, and the ends of the phenyl vinyl ketone element are 2 aromatic anhydrides. In the preparation method, phenyl vinyl ketone containing 2 Ph-OH is obtained by aldol condensation, phenyl vinyl ketone containing 2 alcoholic hydroxy and 2 flexible chains is further obtained by O-alkylation, and the obtained phenyl vinyl ketone containing hydroxyl and trimellitic anhydride acyl chloride are esterified and purified to obtain the dianhydride monomer containing the phenyl vinyl ketone which meets the polycondensation purity requirement. The raw materials used in the preparation method are large-scale industrialization products, the control of the synthetic process is simple, and the obtained dianhydride has higher purity, thereby further meeting requirements for polyimide polymerization production.

Description

technical field [0001] The invention relates to a dianhydride monomer containing a photocrosslinkable phenyl vinyl ketone unit and a preparation method thereof, belonging to the technical field of polymer materials. Background technique [0002] Polyimide (Polyimide) is a class of polymer materials containing imide rings in the main molecular chain. This type of material has superior mechanical, dielectric, insulation, radiation resistance, corrosion resistance, high and low temperature resistance, etc. It is used in various fields such as films, adhesives, coatings, laminated composites, molding compounds and electronic packaging. Especially in the field of electronics, because of its high thermal stability, high resistivity and breakdown voltage, polyimide is usually used as a protective material on integrated circuit boards and thin-film multilayer electronic packaging materials. [0003] When used as an integrated circuit board, polyimide materials are usually used as a...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/89C08G73/10
Inventor 郭妙才和亚宁连彦青王晓工
Owner TSINGHUA UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap