Epoxy-Functional Polyurethane Synthesis Without Glycidol
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Solution Overview
Problem
Current methods for synthesizing epoxy-functional polyurethanes rely on glycidol, which is expensive and poses health hazards, and there is a need for a new approach that does not use glycidol while maintaining the polyurethane backbone's properties such as toughness and durability.
Innovation Solution
The synthesis of epoxy-urethane resins involves reacting a polyisocyanate with a compound containing a hydroxyl group and vinyl groups, where the vinyl groups are oxidized to form epoxy groups, using a process that includes reacting the polyisocyanate with a compound HX-Y-(Z) n, where X is O, N, or S, and Z is capable of being oxidized to an epoxy group, allowing for the formation of epoxy-functional polyurethanes without relying on glycidol.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If glycidol is used to synthesize epoxy-functional polyurethanes, then the polyurethane backbone properties (toughness and durability) are maintained, but the cost increases and health hazards arise
Solution Approach 1:
The patent extracts and removes glycidol from the synthesis process entirely. Instead of using glycidol to introduce epoxy groups, the invention uses vinyl groups that are subsequently oxidized to form epoxy groups in place, eliminating the need for glycidol and its associated health hazards and cost issues while maintaining the epoxy-functional polyurethane structure and properties
Solution Approach 2:
The patent changes the chemical parameter of the synthesis approach by replacing glycidol-based epoxidation with vinyl group oxidation. This parameter change involves using different chemical reactants (vinyl groups instead of glycidol) and a different chemical transformation pathway (oxidation of vinyl groups versus direct glycidol incorporation), thereby eliminating the harmful factors while achieving the same functional result
2Reliability
If traditional epoxy resins are used as primers, then good adhesion and anticorrosion barrier are provided, but the system requires two-component mixing which limits pot life
Solution Approach 1:
The patent segments the epoxy functionality from the polyurethane backbone, creating a hybrid material that combines the adhesion and anticorrosion properties of epoxy resins with the flexibility and durability of polyurethanes. This segmentation allows the material to function as a single-component system while maintaining the protective properties of traditional two-component epoxy systems
Solution Approach 2:
The epoxy-functional polyurethane resin serves multiple functions simultaneously: it provides the adhesion and anticorrosion barrier characteristics of epoxy primers, while also maintaining the toughness and durability of polyurethane coatings. This multi-functionality eliminates the need for separate primer and topcoat applications and removes the pot life limitation associated with two-component mixing
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
This method produces epoxy-functional polyurethanes that can be cured with amines or self-cured, suitable for various applications like coatings, adhesives, and composites, offering improved properties without the use of glycidol, thus addressing the cost and health concerns associated with traditional methods.
Implementation Method 1
wherein the vinyl groups are oxidized to form epoxy groups
Implementation Method 2
reacting a polyisocyanate with a compound containing a hydroxyl group and vinyl groups
Implementation Method 3
These resins can be cured with amines or can self-cure
Data Source
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AI summary
Provided is an epoxy-functional polyurethane comprising a reaction product of (A) a polyisocyanate; and (B) a compound, HX-Y-(Z)n wherein, X is O, N, or S, Y is a linear or branched C1-C15 alkyl group, and Z is -CH=CDE or Z is -F-O-G-CH=CDE, n is an integer from 1 to 3, wherein D and E independently are selected from H, a linear C1-C5 alkyl group, and a branched C1-C5 alkyl group, F and G independently are selected from H, linear or branched C1-C15 alkyl groups, and wherein compound (B) comprises a vinyl group capable of being oxidized to a corresponding epoxy group. Also provided is a process for producing an epoxy-functional polyurethane, the process comprising (1) reacting (A) a polyisocyanate; and (B) a compound: HX-Y-(Z)n wherein, X is O, N, or S, Y is a linear or branched C1-C15 alkyl group, and Z is -CH=CDE or Z is -F-O-G-CH=CDE, n is an integer from 1 to 3, wherein D and E independently are selected from H, a linear C1-C5 alkyl group, and a branched C1-C5 alkyl group, F and G independently are selected from H, linear or branched C1-C15 alkyl groups, optionally, in the presence of a catalyst to form a vinyl-functional carbamate; (2) forming a mixture containing the vinyl-functional carbamate, a ketone, water, and a base; and (3) feeding an aqueous solution of oxone into the mixture to oxidize the vinyl-functional carbamate to the epoxy-functional polyurethane. The epoxy-functional polyurethanes of the invention may find use in or as coatings, adhesives, sealants, films, elastomers, castings, foams, and composites.