Triazole Moieties with Remote Polymerizable Groups
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Solution Overview
Problem
Current copper-catalyzed azide/alkyne chemistry for producing 1,2,3-triazole moieties requires catalyst and solvent removal, and lacks methods to introduce new polymerizable moieties, limiting the versatility and environmental sustainability of the process.
Innovation Solution
The synthesis of 4- and 5-substituted 1,2,3-triazole moieties with remote polymerizable moieties through 1,3-dipolar cycloaddition reactions, allowing for the formation of various polymers without the need for catalyst or solvent removal, and enabling the introduction of diverse polymerizable groups.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If copper-catalyzed azide/alkyne chemistry is used to produce 1,2,3-triazole moieties, then the reaction proceeds under mild conditions with rate acceleration and exclusive 1,4-regioselectivity, but the catalyst and solvent must be removed which adds steps to the synthetic method and creates environmental disposal issues
Solution Approach 1:
The patent extracts and eliminates the copper catalyst from the reaction system by using uncatalyzed azide/alkyne cycloaddition. This removes the need for catalyst removal steps and eliminates environmental disposal issues while maintaining the core triazole formation functionality.
Solution Approach 2:
The patent employs a disposable approach by using readily available azide and alkyne reagents that react directly without requiring expensive or sensitive catalyst systems. The reaction proceeds under ambient conditions with simple workup, treating the system as disposable rather than requiring meticulous catalyst management.
2Temperature
If copper-catalyzed azide/alkyne chemistry is used to produce 1,2,3-triazole moieties, then the reaction proceeds under mild conditions, but the method lacks versatility to introduce new polymerizable moieties
Solution Approach 1:
The patent creates a universal platform where the triazole core can be functionalized with various polymerizable moieties (acrylates, methacrylates, vinyl groups, epoxies, oxetanes) through the cycloaddition reaction. This single method can introduce multiple different functional groups, making the system multi-functional and highly versatile for polymer applications.
Solution Approach 2:
The patent applies local quality by placing different polymerizable functional groups at specific positions on the triazole ring (positions 4 and 5) through selective functionalization of the azide or alkyne components. This allows tailoring of local chemical properties at different sites of the molecule while maintaining the core triazole structure.
3Ease of manufacture
If copper-catalyzed azide/alkyne chemistry is used, then triazole polymer moieties can be prepared as metal adhesives, but the catalyst disposal adds steps and environmental impact
Solution Approach 1:
The patent converts the potential harm of copper catalyst disposal into a benefit by eliminating the catalyst entirely. The uncatalyzed reaction proceeds sufficiently well under ambient conditions to produce the desired triazole polymers, turning what would have been a harmful waste stream into a clean, environmentally friendly process.
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
This approach provides a sustainable and versatile method for producing triazole-based polymers with enhanced thermal and chemical stability, suitable for a wide range of applications including adhesives, coatings, and personal care products, while avoiding the environmental impact of catalyst and solvent disposal.
Implementation Method 1
The novel compounds are prepared by the ligation of azides and alkynes using 1,3-dipolar cycloaddition reactions
Data Source
AI summary
The present invention provides novel 4- and 5-substituted 1,2,3-triazole moieties, with at least one remote polymerizable moiety. The novel mixtures of 4- and 5-substituted regioisomers of 1,2,3-triazole moieties can be separated by chromatography to provide the purified 4- and 5-substituted 1,2,3-triazole moieties. The novel mixtures of 4- and 5-substituted regioisomers of 1,2,3-triazole moieties, and the purified 4- and 5-substituted 1,2,3-triazole moieties, with at least one remote polymerizable moiety, can be converted to a wide variety of useful polymers. The novel compounds of the invention can be employed in a wide variety of compositions. E, Q, Z, X, a, and R1-R4, in the structures below, are defined herein.