Alkene Isomerization for Alternating Ring-Opening Metathesis Polymerization
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Solution Overview
Problem
Current methods for synthesizing alternating polymers are limited, lacking structural diversity and precision in monomer sequence control, which restricts the development of polymers with complex structural and functional properties.
Innovation Solution
A method involving the isomerization of cyclobutene derivatives in the presence of an olefin metathesis catalyst, followed by ring-opening cross metathesis with cyclohexene derivatives, to produce rigorously alternating AB copolymers with controlled functional group arrangements and low polydispersities.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If radical polymerization with kinetic control is used to synthesize alternating polymers, then alternation in the polymerization reaction is achieved, but structural diversity and precision in monomer sequence control are limited
Solution Approach 1:
The patent employs ring-opening metathesis polymerization (ROMP) and ring-opening insertion metathesis polymerization (ROIMP) as alternative polymerization mechanisms to radical polymerization. By changing the polymerization mechanism and using specific catalyst systems, the invention achieves precise alternation control through the inherent mechanism of metathesis reactions rather than kinetic control, thereby improving monomer sequence control while enabling access to diverse monomer structures that are not accessible via radical polymerization.
2Manufacturing precision
If existing methods for forming alternating polymers are used, then some alternating polymer structures are obtained, but substrate and catalyst combinations are limited
Solution Approach 1:
The patent utilizes metathesis catalysts that can function with a wide variety of monomer substrates. The same catalyst system (e.g., Grubbs catalysts, Schrock catalysts) can polymerize different cycloolefin monomers including norbornene, isobornene, bicyclo[2.2.1]hept-5-ene-2-carboxylic acid derivatives, and other strained ring olefins. This multi-functionality of the catalyst system expands the range of accessible alternating polymer structures while maintaining precise alternation control, thereby improving ease of manufacture for diverse substrate combinations.
3Manufacturing precision
If ROMP and ROIMP are employed to synthesize alternating polymers, then alternating copolymer structures are formed, but structural diversity and property range are restricted
Solution Approach 1:
The patent synthesizes alternating copolymers by combining different cycloolefin monomers (A monomers such as norbornene, isobornene, bicyclo[2.2.1]hept-5-ene-2-carboxylic acid derivatives) with complementary monomers (B monomers) through metathesis polymerization. By selecting monomers with specific functional groups, stereochemistry, and physical properties, the invention creates composite alternating copolymer structures that exhibit tailored properties including amphiphilicity, chirality, and diverse functional characteristics. This approach to composite material design through monomer selection expands the property range of accessible alternating polymers while maintaining precise alternating structure.
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
Facilitates the preparation of long, alternating AB copolymers with precise sequence control, enabling the creation of polymers with enhanced structural and functional complexity, including high molecular weights and narrow molecular weight distributions.
Implementation Method 1
In a first step the cyclobutene III is isomerized to III′ in the presence of an olefin metathesis catalyst. The method comprises isomerizing the cyclobutene 1-carboxyl or 1-carbonyl derivative III to isomerized cyclobutene 1-carboxyl or 1-carbonyl derivative III′ in the presence of an olefin metathesis catalyst.
Data Source
AI summary
This invention relates to the field of polymers and olefin polymerization, and more specifically olefin metathesis polymerization. Specifically, the present invention provides a polymer comprising rigorously alternating AB subunits and methods of formation of the AB alternating polymers. In the polymers and process of the invention, the A monomer is derived from a cyclobutene derivative, and the B monomer is derived from a cyclohexene derivative. The polymerization takes place in the presence of an olefin metathesis catalyst.