Bio-based Polyester Resin Toner via Diels-Alder Adducts
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Solution Overview
Problem
Current bio-based polyester resins for toners have limitations due to the restricted range of available bio-based diols and diacids, resulting in toners with low glass transition temperature and high equilibrium moisture content, which adversely affect charging and fusing properties.
Innovation Solution
Incorporating a bio-based cyclohexadiene Diels-Alder reaction adduct, derived from essential oil components like α-terpinene and α-phellandrene, into polyester resin formulations to enhance the molecular weight and carbon-oxygen ratio, thereby improving the physico-chemical properties of toners.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Adaptability or versatility
If bio-based diols and diacids are used to prepare polyester for toner, then the toner has high bio-based content, but the glass transition temperature is low and equilibrium moisture content is high
Solution Approach 1:
The patent uses composite monomers combining bio-based components (cyclohexadiene from essential oils) with petroleum-based components (maleic anhydride, fumaric acid) to create a polyester resin that achieves both high bio-based content and adequate glass transition temperature. The cyclohexadiene provides the bio-based content while the maleic anhydride/fumaric acid contributes to structural rigidity and higher Tg.
Solution Approach 2:
The patent changes the chemical structure parameters of the monomers by selecting cyclohexadiene with specific substitution patterns (α-terpinene or α-phellandrene) and reacting with dicarboxylic acids or cyclic anhydrides to produce adducts with optimized carbon-oxygen ratios and molecular weights that achieve the desired glass transition temperature range.
2Adaptability or versatility
If bio-based diols and diacids are used to prepare polyester for toner, then the toner has high bio-based content, but the equilibrium moisture content is high
Solution Approach 1:
The patent creates a composite monomer system where the cyclohexadiene-based bio component is combined with maleic anhydride or fumaric acid to form a Diels-Alder adduct. This composite structure reduces the hydrophilicity compared to pure bio-based monomers, thereby lowering the equilibrium moisture content while maintaining high bio-based content.
Solution Approach 2:
The patent optimizes the carbon-oxygen ratio parameter by selecting specific cyclohexadiene derivatives and dicarboxylic acid components, creating adducts with reduced oxygen content relative to carbon. This parameter change decreases the hydrophilicity of the polyester resin, resulting in lower equilibrium moisture content.
3Reliability
If petroleum-based monomers are included in resin formulations, then charge and fusing properties are improved, but the bio-based content is reduced
Solution Approach 1:
The patent creates a composite monomer where the hydrophobic cyclohexadiene component (from essential oils) is chemically bonded to maleic anhydride or fumaric acid. This composite structure inherently provides the hydrophobicity and structural rigidity needed for good charging and fusing properties, eliminating or reducing the need for additional petroleum-based monomers like terephthalic acid or cyclohexene dicarboxylic acid.
Solution Approach 2:
The cyclohexadiene component from essential oils inherently provides the necessary hydrophobic character and molecular structure to achieve good charging and fusing properties without requiring supplementation with petroleum-based monomers. The monomer serves its own function of providing both bio-based content and adequate performance properties.
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 use of bio-based Diels-Alder adducts in toner resins addresses the limitations of existing bio-based monomers by enhancing the glass transition temperature and fusing properties, achieving performance comparable to petroleum-based monomers while maintaining a high bio-based content.
Implementation Method 1
a Diels-Adler reaction adduct, where the diene comprises a substituted cyclohexadiene component of an essential oil, the dienophile comprises maleic acid, maleic anhydride or fumaric acid, and the resulting adduct is a bicyclic compound
Data Source
AI summary
A polyester resin is described which includes bio-based, cyclohexadiene Diels-Alder reaction adduct monomer for use in toner for imaging devices.