Isosorbide-Based Polymethacrylates for Renewable High-Tg Polymers
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Solution Overview
Problem
Current high-Tg polymers, such as polystyrene and poly(methyl methacrylate), are predominantly derived from non-renewable petroleum-based feedstocks, prompting a need for renewable alternatives with similar performance characteristics.
Innovation Solution
Development of a dianhydrohexitol-based monomer, specifically isosorbide-based monomers, which can be polymerized to form glassy acrylate or methacrylate polymers with high glass transition temperatures and good thermal stability, using a process involving acylation and subsequent reaction with acrylic compounds, and further polymerization with chain-transfer agents to create block copolymers.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Temperature
If petroleum-based feedstocks are used to produce high-Tg polymers, then the polymers achieve high glass transition temperatures and good thermal stability, but the feedstock is non-renewable
Solution Approach 1:
The patent changes the chemical composition parameters by substituting petroleum-based monomers with isosorbide-based monomers containing acrylate or methacrylate groups. This parameter change maintains the glass transition temperature (≥130°C) and thermal stability while transforming the feedstock from non-renewable to renewable biomass-derived sources.
Solution Approach 2:
The patent employs readily available, inexpensive renewable feedstocks (isosorbide from biomass) to replace expensive or depleting petroleum resources. The approach uses abundant biological materials that can be sustainably replenished, effectively treating the feedstock as a renewable resource rather than a finite one.
2Adaptability or versatility
If renewable feedstocks are used to produce polymers, then the polymers become sustainable and environmentally friendly, but the glass transition temperature and thermal stability may be reduced
Solution Approach 1:
The patent applies local quality by introducing specific functional groups (acrylate or methacrylate) at key positions of the isosorbide molecule. This localized functionalization allows the polymer to achieve both renewable feedstock origin and high glass transition temperature (≥130°C), as the rigid cyclic structure of isosorbide combined with the reactive vinyl groups creates the desired thermal properties.
Solution Approach 2:
The patent creates composite molecular structures by combining the rigid bicyclic isosorbide core with acrylate or methacrylate side groups. This composite approach leverages the thermal stability of the cyclic structure and the polymerization capability of the vinyl groups, achieving both sustainability and high performance.
3Ease of manufacture
If traditional polymerization methods are used, then the production process is simple and cost-effective, but the polymers cannot achieve high glass transition temperatures with renewable feedstocks
Solution Approach 1:
The patent achieves universality by designing an isosorbide-based monomer that can undergo standard free radical polymerization while simultaneously delivering high glass transition temperature (≥130°C). The monomer structure is engineered to be compatible with conventional polymerization methods, making the process both simple and effective for producing high-performance renewable polymers.
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 polymers exhibit high glass transition temperatures (at least 130°C) and thermal stability, comparable to traditional polymers like PMMA, while being derived from renewable sources, offering a sustainable alternative for various applications.
Implementation Method 1
reacting a dianhydrohexitol precursor having the structure (II) with an acyl-group containing compound having the structure (VI) to form an acylated dianhydrohexitol ester intermediate having the structure (IX)
Implementation Method 2
reacting the acylated dianhydrohexitol ester intermediate with an acrylic-based compound having the structure (XIII) to form a dianhydrohexitol-based monomer having the structure (I)
Implementation Method 3
The dianhydrohexitol-based monomer can be polymerized to form a polymer with a relatively high glass transition temperature (e.g., at least about 130° C.) and good thermal stability
Data Source
AI summary
A monomer comprises the structurewherein R1 comprises H or a substituted hydrocarbyl or unsubstituted hydrocarbyl, and wherein R2 comprises H, a halide, or a substituted or unsubstituted (C1-C4) hydrocarbyl. A method comprises (a) reacting a dianhydrohexitol precursor having the structurewith an acyl-group containing compound having the structurewherein R1 comprises H or a substituted hydrocarbyl or unsubstituted hydrocarbyl, and X comprises a halide, a hydroxyl group, or an acyl group to form an acylated dianhydrohexitol ester intermediate having the structureand (b) reacting the acylated dianhydrohexitol ester intermediate with an acrylic-based compound having the structurewherein R2 comprises H, a halide, or a substituted or unsubstituted (C1-C4) hydrocarbyl, and Y comprises a halide, a hydroxyl group, or an acyl group, to form a dianhydrohexitol-based monomer having the structure