Norbornane Divinyl Ether Synthesis for UV Transmission
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Solution Overview
Problem
There is a need for novel divinyl ether compounds with improved stability, curability, adhesiveness, and ultraviolet light transmission, which are not met by existing divinyl ether compounds like pentaerythritol acetal divinyl ether and 1,3-adamantane dimethanol divinyl ether due to their hydrolysis and cyclization polymerization issues.
Innovation Solution
The synthesis of 2,2-bis[(ethenyloxy)methyl]bicyclo[2.2.1]heptane and 5,5-bis[(ethenyloxy)methyl]bicyclo[2.2.1]hept-2-ene through the reaction of 2,2-norbornanedimethanol or 5-norbornene-2,2-dimethanol with acetylene in the presence of an alkaline catalyst in an aprotic polar solvent.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If pentaerythritol acetal divinyl ether is used, then curability is improved, but stability to water deteriorates due to easy hydrolysis of the acetal structure
Solution Approach 1:
The patent changes the chemical structure parameter by replacing the acetal group with a cyclic ether group, which fundamentally alters the stability characteristics while preserving the divinyl ether functionality needed for curability
Solution Approach 2:
The patent creates a composite molecular structure combining the norbornane cyclic framework with divinyl ether side groups, achieving both water stability and curability through the synergistic combination of structural rigidity and reactive functionality
2Stability of the object's composition
If 1,3-adamantane dimethanol divinyl ether is used, then structural stability is improved, but ease of operation deteriorates due to easy cyclization polymerization
Solution Approach 1:
The patent modifies the core structural parameter by replacing the adamantane cage structure with a norbornane bicyclic structure, which changes the spatial arrangement and reduces steric hindrance, thereby controlling the cyclization polymerization behavior while maintaining structural stability
Solution Approach 2:
The patent applies local quality by positioning the divinyl ether groups at specific locations (2,2- or 5,5-positions) on the norbornane ring, creating localized reactive sites that enable controlled polymerization while the rigid bicyclic framework provides overall structural stability
3Stability of the object's composition
If novel divinyl ether compounds with bicyclo[2.2.1]heptane structure are developed, then stability to water and control of cyclization polymerization are improved, but device complexity increases due to novel synthesis requirements
Solution Approach 1:
The patent applies preliminary action by first synthesizing the norbornane diol core structure, then performing the vinyl etherification reaction in a sequential two-step process, which simplifies the overall synthesis by breaking down the complex transformation into manageable stages with well-defined intermediates
Solution Approach 2:
The patent uses the norbornane diol as an intermediary compound that bridges the simple starting materials and the final divinyl ether product, providing a stable intermediate structure that facilitates controlled synthesis while ensuring water stability in the final product
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 divinyl ether compounds exhibit low odor, low volatility, low skin irritability, and low toxicity, with enhanced properties suitable for polymer compositions, offering excellent curability, adhesiveness, and ultraviolet light transmission, making them useful in various applications such as inks, paints, and photoresists.
Implementation Method 1
reacting 2,2-norbornanedimethanol or 5-norbornene-2,2-dimethanol having the formula (II) with acetylene in the presence of an alkaline compound catalyst in an aprotic polar solvent
Data Source
AI summary
A novel divinyl ether compound having the formula (I):wherein A indicates a single bond or a double bondwhich is low in odor, low in volatility, and low in skin irritability, which have low toxicities, which are useful as a starting material for a polymer composition having excellent curability, adhesiveness and transmission in the ultraviolet light region, and further, having a special reactivity alone or with other compounds, and a process for producing the same.