Vinyl-Blocked Bio-Based Acids for Homogeneous Epoxy Coatings
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Solution Overview
Problem
Current bio-based thermosets using petrochemical-derived cyclic anhydrides as crosslinkers are not fully bio-based, and polyfunctional carboxylic acids in their crystalline solid form have difficulty forming homogeneous mixtures with epoxy resins, resulting in materials with poor properties.
Innovation Solution
The reaction of bio-based polyfunctional carboxylic acids with vinyl ether compounds to create liquid vinyl-blocked bio-based polyfunctional carboxylic acids, which can be mixed with polyfunctional vegetable oil-based epoxy resins to form thermoset coatings with enhanced hardness, solvent resistance, and flexibility upon curing.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Stability of the object's composition
If polyfunctional carboxylic acids in crystalline solid form are used, then the material is fully bio-based, but it forms non-homogeneous mixtures with epoxy resins resulting in poor material properties
Solution Approach 1:
The patent changes the physical state parameter of the carboxylic acid from crystalline solid to liquid by blocking the carboxylic acid groups with vinyl ether compounds. This parameter change enables homogeneous mixing with epoxy resins while maintaining the bio-based nature of the material.
Solution Approach 2:
The vinyl ether blocking group acts as an intermediary that temporarily masks the carboxylic acid functionality, allowing the acid to be handled and mixed in liquid form. The blocking group can be removed during curing to restore the carboxylic acid functionality for crosslinking.
2Stability of the object's composition
If polyfunctional carboxylic acids in crystalline solid form are used, then the material is fully bio-based, but the mixing process becomes difficult resulting in poor material properties
Solution Approach 1:
The patent changes the physical state parameter of the carboxylic acid from crystalline solid to liquid by blocking the carboxylic acid groups with vinyl ether compounds. This parameter change enables homogeneous mixing with epoxy resins while maintaining the bio-based nature of the material.
3Reliability
If petrochemical-derived cyclic anhydrides are used as crosslinkers, then the material has good performance properties, but the material is not fully bio-based
Solution Approach 1:
The patent changes the chemical composition by replacing petrochemical-derived cyclic anhydrides with bio-based polyfunctional carboxylic acids. The vinyl blocking temporarily modifies these acids to enable processing, while their polyfunctional nature allows them to serve as effective crosslinkers for achieving good performance properties.
4Stability of the object's composition
If crystalline solid carboxylic acids are used, then the material is fully bio-based, but the resulting thermoset has poor hardness, solvent resistance, and flexibility
Solution Approach 1:
The patent changes the physical state parameter of the carboxylic acid from crystalline solid to liquid by blocking the carboxylic acid groups with vinyl ether compounds. This parameter change enables homogeneous mixing with epoxy resins while maintaining the bio-based nature of the material.
Solution Approach 2:
The patent achieves homogeneous distribution of the bio-based carboxylic acid throughout the epoxy resin matrix by using the liquid vinyl-blocked form during mixing. This homogeneity ensures uniform crosslinking and consistent performance properties including hardness, solvent resistance, and flexibility.
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 thermoset coatings exhibit excellent hardness, solvent resistance, and flexibility, overcoming the limitations of poor properties in previous bio-based materials by ensuring a homogeneous mixture and full bio-based content.
Implementation Method 1
The reaction of bio-based polyfunctional carboxylic acids with vinyl ether compounds to create liquid vinyl-blocked bio-based polyfunctional carboxylic acids
Implementation Method 2
Upon curing the homogeneous mixtures at elevated temperature, thermoset coatings are formed
Data Source
AI summary
This invention relates to bio-based polyfunctional carboxylic acids reacted with vinyl ether compounds to form liquid vinyl-blocked bio-based polyfunctional carboxylic acids. These liquid vinyl-blocked bio-based polyfunctional carboxylic acids can be mixed with a polyfunctional vegetable oil-based epoxy resin to form a homogeneous curable coating composition. Upon curing at elevated temperature, thermoset coatings are formed which have excellent hardness, solvent resistance, adhesion, and flexibility. The invention also relates to the use of a curable coating composition comprising at least one polyfunctional vegetable oil-based epoxy resin and at least one vinyl-blocked bio-based polyfunctional carboxylic acid, which may be coated onto a substrate and cured thermally. Methods of making the vinyl-blocked bio-based polyfunctional carboxylic acids and curable coating compositions and substrates containing the same are also disclosed.