Cyclohexane Dimethanol Acrylate Monomer Liquid Formulation
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Solution Overview
Problem
Radiation-cured coatings and inks based on cyclohexane dimethanol diacrylates are difficult to use due to their solid state at room temperature and poor end-use properties, while liquid formulations have inferior performance.
Innovation Solution
A mixture of cyclohexane dimethanol-based acrylates and methacrylates that are liquid at room temperature, comprising a blend of cis and trans-1,3- and 1,4-substituted cyclohexane, with a trans-1,4-substituted cyclohexane content less than 40 mole percent, which can be used to produce coatings with excellent hardness, strength, clarity, abrasion resistance, adhesion, and solvent resistance.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Strength
If cyclohexane dimethanol diacrylates are used in radiation cured coatings, then the cured coating has excellent hardness and strength, but the formulations are difficult to use because the cyclohexane dimethanol diacrylates are solid materials at room temperature and often are insoluble in most acrylates
Solution Approach 1:
The patent changes the physical state parameter of the cyclohexane dimethanol diacrylate from solid to liquid at room temperature by modifying the molecular structure (using cis-1,3- and trans-1,4-cyclohexane dimethanol with specific isomer ratios), enabling the material to be handled as a liquid while maintaining the desired coating performance properties
Solution Approach 2:
The patent creates a composite formulation by combining liquid cyclohexane dimethanol diacrylate with other acrylate components, achieving both good solubility/miscibility and excellent cured coating properties through the synergistic combination of materials
2Ease of operation
If ethoxylated or propoxylated cyclohexane dimethanol diacrylates are used to create liquid formulations, then the formulations are easier to use, but the resulting coating has poorer end use properties
Solution Approach 1:
The patent modifies the molecular structure parameter by selecting specific cyclohexane dimethanol isomers (cis-1,3- and trans-1,4-) with controlled isomer ratios, achieving the desired liquid state and coating performance without requiring ethoxylated or propoxylated modifications that compromise end-use properties
3Strength
If trans-1,4-substituted cyclohexane content is increased to improve coating performance, then the coating properties improve, but the material becomes more difficult to process and formulate
Solution Approach 1:
The patent optimizes the isomer composition parameter by controlling the trans-1,4-substituted cyclohexane content to be less than 40 mole percent, achieving a balance between coating performance and ease of formulation/processing by preventing the material from becoming too viscous or solid-like while still providing excellent cured 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 solution provides coatings with enhanced mechanical and chemical properties, including high hardness, excellent adhesion, and resistance to abrasion and solvents, while maintaining a liquid state at room temperature.
Implementation Method 1
Radiation cured (typically free radical UV light photopolymerization) coatings and inks are widely used in the coatings and printing industry
Implementation Method 2
distilling a mixture of cis and trans-1,3- and 1,4-methanol substituted cyclohexane wherein the trans-1,4-methanol substituted cyclohexane content of the compounds is greater than twenty five mole percent to produce a distilled fraction and a residue fraction
Data Source
AI summary
A mixture of compounds useful to make a polymer or a prepolymer, the mixture of compounds including compounds having the formula I; wherein R1 is H, acryloyl, methacryloyl or vinyl, wherein R2 is acryloyl, methacryloyl or vinyl, wherein compounds having the formula I consist of a mixture of cis and trans-1,3- and 1 ,4-substituted cyclohexane and wherein the trans- 1,4-substituted cyclohexane content of the compounds having the formula I is less than forty mole percent. A process for producing a mixture of compounds including compounds having the formula II: wherein compounds having the formula II consist of a mixture of cis and trans- 1,3- and 1 ,4- methanol substituted cyclohexane and wherein the trans- 1,4-methanol substituted cyclohexane content of the compounds having the formula II is less than twenty five mole percent.