Fused Bicyclic Polyisocyanates from Renewable Polyols
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Solution Overview
Problem
Current methods for producing polyisocyanates from renewable sources are often low-yielding and require expensive catalysts, lacking environmental friendliness and cost-effectiveness, while polyurethanes derived from these methods may require toxic solvents and have inferior properties compared to petroleum-based counterparts.
Innovation Solution
The development of polyisocyanates and polyurethanes derived from fused bicyclic alcohols, such as isosorbides, using environmentally friendly techniques that avoid toxic reagents and reduce waste, with methods involving the reaction of fused bicyclic polyols with acid anhydrides, acyl halide generators, and azide generators to produce polyisocyanates that can form aqueous dispersions without volatile organic solvents.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Object-affected harmful factors
If polyisocyanates are produced from renewable sources using conventional methods, then environmental friendliness is improved, but production yield is low and catalyst cost is high
Solution Approach 1:
The patent changes the chemical parameters of the synthesis route by using fused bicyclic polyols with specific structural characteristics (rigid cyclic structures) and optimizing reaction conditions with acid anhydrides and azide generators. This transforms the low-yielding conventional process into a high-yielding method while maintaining renewable source material usage and environmental friendliness.
2Object-affected harmful factors
If polyisocyanates are produced from renewable sources using conventional methods, then environmental friendliness is improved, but production cost is high
Solution Approach 1:
The patent replaces expensive catalysts required in conventional methods with a catalytic system using acid anhydrides and azide generators that are more cost-effective. The method uses readily available reagents and avoids the need for expensive metal catalysts, thereby reducing production cost while maintaining environmental friendliness through renewable feedstocks.
3Ease of manufacture
If polyurethanes are made from conventional polyisocyanates, then manufacturing is simplified, but toxicity increases due to required solvents
Solution Approach 1:
The patent extracts and eliminates the need for toxic volatile organic solvents from the polyurethane manufacturing process. The polyisocyanates derived from fused bicyclic polyols have inherent properties that allow them to react with polyols to form polyurethanes without requiring toxic solvent media, thereby maintaining manufacturing simplicity while removing the harmful solvent component.
4Strength
If polyurethanes are made from petroleum-based materials, then material properties are superior, but environmental impact increases
Solution Approach 1:
The patent creates composite material properties by utilizing the rigid fused bicyclic structure (such as isosorbide-derived polyols) combined with polyisocyanate moieties. The rigid cyclic structures provide inherent strength and rigidity to the polyurethane, compensating for any potential property deficiencies compared to petroleum-based materials, while the renewable origin reduces environmental impact.
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 approach results in polyurethanes with improved strength, rigidity, biodegradability, and cost-effectiveness, using renewable materials and reducing environmental impact, while allowing for the formation of aqueous dispersions without the need for harmful solvents.
Implementation Method 1
contacting a compound having the structure (I) with an acid anhydride having the structure (II) to provide a polyacid having the structure (I) wherein R'' is C(O)OH
Implementation Method 2
contacting the polyacid and an acyl halide generator. Contacting the polyacid and the acyl halide generator provides a polyacid halide having the structure of Formula (I) where R'' is C(O)X, wherein X is halide
Implementation Method 3
contacting the polyacid halide and an azide generator under conditions suitable to provide a polyisocyanate having the structure of Formula (I) where R'' is NCO
Data Source
AI summary
The present invention is directed to polyisocyanates and polyurethanes derived therefrom. In various embodiments, the present invention provides polyisocyanates, methods of making the polyisocyanates from fused bicyclic alcohols, polyurethanes, and methods of making the polyurethanes from the polyisocyanates.