Para-phenylenediamine Derivatives for Polyimide Resin Solubility
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Solution Overview
Problem
Current monomers used in synthesizing polyimide resins for flexible displays, such as para-phenylenediamine and 1,4-diamine cyclic compounds, have low solubility, leading to premature precipitation and limited molecular weight due to their low solubility, which hampers the polymerization process.
Innovation Solution
Development of para-phenylenediamine and 1,4-cyclohexanediamine derivatives with specific hydrocarbon groups that enhance solubility, along with a method involving thermal processes using monohydric alcohol and para-toluenesulfonic acid to facilitate polymerization, allowing for the selective production of these derivatives as monomers for polyimide resins.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If conventional monomers (para-phenylenediamine and 1,4-diamine cyclic compounds) are used for synthesizing polyimide resins, then the polymerization reaction can proceed, but the low solubility of these monomers causes premature precipitation and limited molecular weight
Solution Approach 1:
The patent modifies the molecular structure of conventional monomers by introducing specific substituent groups (such as alkoxy groups, alkyl groups, or heteroatom-containing groups) at designated positions of the phenylenediamine or cyclohexanediamine core structure. These structural parameter changes enhance the solubility of the monomers in common solvents while maintaining their reactivity for polymerization, thereby preventing premature precipitation and enabling the formation of high molecular weight polyimide resins.
2Reliability
If the solubility of monomers is improved by structural modification, then polymerization can proceed more effectively, but the complexity of monomer synthesis increases
Solution Approach 1:
The patent applies local quality modification by introducing solubility-enhancing substituent groups only at specific positions (such as positions 2, 3, 5, or 6 relative to the diamine group) rather than modifying the entire molecular structure. This localized modification approach improves solubility while minimizing the increase in overall molecular complexity and maintaining the essential reactivity of the monomers.
3Adaptability or versatility
If multiple separate processes are used to fabricate different diamine derivatives, then product selectivity can be achieved, but production costs and process complexity increase
Solution Approach 1:
The patent develops a universal synthetic route that can produce different diamine derivatives (both para-phenylenediamine and 1,4-cyclohexanediamine derivatives) through a common multi-step process framework. By utilizing the same core synthetic methodology with adjustable parameters and intermediates, the process can selectively yield different target products, thereby reducing overall process complexity and manufacturing costs while maintaining product selectivity.
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 derivatives improve solubility and reactivity, enabling higher molecular weight polymers and reducing production costs by allowing for the selective control of reaction conditions in a single method, enhancing the convenience of monomer fabrication.
Implementation Method 1
performing a first thermal process which includes using monohydric alcohol and para-toluenesulfonic acid for an addition reaction of para-nitroacetaniline
Implementation Method 2
performing a second thermal process which includes performing a reduction reaction on the first compound
Implementation Method 3
performing a third thermal process which includes performing a reduction reaction on the second compound
Data Source
AI summary
A fabricating method for a 1,4-diamine cyclic compound derivative includes: performing a first thermal process to form a first compound, in which the first compound has a structure represented by formula (i):in which R represents a C1 to C12 hydrocarbon group; performing a second thermal process, which includes performing a reduction reaction on the first compound to form a second compound, in which the second compound has a structure represented by formula (ii),and performing a third thermal process, which includes performing a reduction reaction on the second compound to form the 1,4-diamine cyclic compound derivative, in which the 1,4-diamine cyclic compound derivative has a structure represented by formula (I) or formula (II):in which R represents a C1 to C12 hydrocarbon group,in which R represents a C1 to C12 hydrocarbon group.