Cage-Shaped Dianhydride Polyimide Transparency Heat Resistance

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Solution Overview

Problem

Conventional polyimides used in electronic materials and optical waveguides face challenges with transparency, solubility in organic solvents, and heat resistance, particularly due to their dark color and low degree of polymerization, which limits their application in high-transparency and high-temperature environments.

Innovation Solution

A cage-shaped cyclopentanetetracarboxylic dianhydride is developed, which increases the linearity of the polyimide structure, enhancing its heat resistance and solubility in organic solvents, and is produced through a method involving esterification, isomerization, decomposition, and dehydration steps, resulting in a polyimide with improved properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If a total aromatic polyimide is used to achieve good mechanical strength and heat resistance, then the polyimide exhibits excellent insulating properties, but it has dark amber color and poor transparency

Engineering Contradiction:
Improveheat resistanceVSAvoidtransparency
Core Design Contradiction:
TemperatureVSIllumination intensity

Solution Approach 1:

The invention changes the chemical structure parameters of the polyimide by introducing alicyclic tetracarboxylic dianhydride units into the polymer chain. This structural modification alters the electronic properties and light absorption characteristics of the material, transforming it from dark amber to highly transparent while preserving heat resistance through careful selection of aromatic diamine components.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite polyimide structure by combining alicyclic tetracarboxylic dianhydride units with aromatic diamine units in the polymer chain. This composite approach allows the material to inherit heat resistance from the aromatic components while achieving transparency through the alicyclic segments, effectively resolving the transparency-heat resistance contradiction.

Inventive Principle:
Principle #40Composite materials

2Illumination intensity

If an unsubstituted alicyclic tetracarboxylic dianhydride is used to achieve good transparency, then the polyimide exhibits high transparency with less discoloration, but it has poor solubility in ordinary organic solvents

Engineering Contradiction:
ImprovetransparencyVSAvoidsolubility in organic solvents
Core Design Contradiction:
Illumination intensityVSEase of manufacture

Solution Approach 1:

The invention modifies the solubility parameters of the polyimide by introducing substituent groups (such as alkyl, alkoxy, or halogen atoms) onto the alicyclic tetracarboxylic dianhydride units. These substituent changes alter the intermolecular forces and packing density of the polymer chains, enhancing solubility in ordinary organic solvents while preserving the transparency advantage of the alicyclic structure.

Inventive Principle:
Principle #35Parameter changes

3Illumination intensity

If a polyimide is formed from 1,2,3,4-cyclopentanetetracarboxylic acid-1:2,3:4-dianhydride to achieve transparency, then the polyimide exhibits good transparency, but it has low degree of polymerization and insufficient heat resistance

Engineering Contradiction:
ImprovetransparencyVSAvoidheat resistance
Core Design Contradiction:
Illumination intensityVSTemperature

Solution Approach 1:

The invention changes the molecular weight parameters and degree of polymerization by optimizing the polymerization conditions and selecting appropriate aromatic diamine counterparts. This increases the chain length and crosslinking density of the polyimide, thereby enhancing heat resistance while maintaining the transparency provided by the alicyclic tetracarboxylic dianhydride units.

Inventive Principle:
Principle #35Parameter changes

4Strength

If conventional polyimide processing is used to achieve good mechanical strength, then the polyimide exhibits excellent insulating properties, but it requires heating at high temperatures for solvent removal which adversely affects organic EL elements

Engineering Contradiction:
Improvemechanical strengthVSAvoidthermal damage to organic materials
Core Design Contradiction:
StrengthVSObject-affected harmful factors

Solution Approach 1:

The invention changes the thermal processing parameters by introducing polyimides with improved solubility through substituent modifications. This allows the polymer to be processed from solution at lower temperatures, eliminating the need for high-temperature solvent removal that would damage sensitive organic EL elements, while still achieving the required mechanical strength through optimized polymer composition.

Inventive Principle:
Principle #35Parameter changes

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The resulting polyimide exhibits high transparency, excellent heat resistance, and good solubility in organic solvents, making it suitable for use in electronic devices and optical communications without UV absorption, thus overcoming the limitations of conventional polyimides.

Implementation Method 1

polycondensation reaction between an aromatic tetracarboxylic dianhydride and an aromatic diamine

Methodology Applied
Scientific EffectPolycondensation reaction: Chemical Bonding

Implementation Method 2

form its film from polyamic acid as its precursor by dehydrocyclization with heating

Methodology Applied
Scientific EffectDehydrocyclization: Chemical Bonding

Implementation Method 3

method involving esterification, isomerization, decomposition, and dehydration steps

Methodology Applied
Scientific EffectEsterification: Chemical Bonding

Implementation Method 4

method involving esterification, isomerization, decomposition, and dehydration steps

Methodology Applied
Scientific EffectIsomerization: Chemical Bonding

Implementation Method 5

method involving esterification, isomerization, decomposition, and dehydration steps

Methodology Applied
Scientific EffectDecomposition: Decomposition (biological)

Implementation Method 6

method involving esterification, isomerization, decomposition, and dehydration steps

Methodology Applied
Scientific EffectDehydration: Chemical Bonding

Data Source

PatentUS8975365B2Cage-shaped cyclopentanoic dianhydride, method for production thereof, and polyimide
Publication Date: 2015.03.10 NISSAN CHEM CORP
  • US8975365B2 patent drawing
  • US8975365B2 patent drawing
  • US8975365B2 patent drawing

AI summary

A cage 1,2,3,4-cyclopentanetetracarboxylic acid (1,3:2,4)-dianhydride compound represented by formula [1], and a polyimide obtained by condensing the compound with a diamine. With the compound, it is possible to provide a polyimide which shows no absorption in the ultraviolet region and is highly transparent to light, has high insulating properties, has improved heat resistance and processability, and has excellent solubility in organic solvents.(In formula [1], R1 and R2 each independently represents a hydrogen atom, a halogen atom, or a C1-10 alkyl.)