Cyclic Carbonate Functional Polyester Synthesis via Beta-Electron Withdrawing Groups
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Solution Overview
Problem
Conventional polyurethane coatings, adhesives, and sealants containing isocyanates pose toxicological risks and form low molecular weight polyurethanes due to limited reactivity and selectivity of cyclic carbonates, making them unsuitable for widespread use.
Innovation Solution
A method involving the reaction of glycerine carbonate with an anhydride to form an adduct, which is then reacted with a polyepoxide compound to produce cyclic carbonate functional polyesters, enhancing reactivity and molecular weight through electron withdrawing groups in the beta position.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Object-affected harmful factors
If conventional cyclic carbonates are used to form NCO-free polyurethanes, then toxicological risks are reduced, but reactivity is limited and molecular weight is low
Solution Approach 1:
The patent modifies the cyclic carbonate structure by introducing electron-withdrawing groups (such as ester or ether moieties) at the beta position relative to the cyclic carbonate group. This structural parameter change increases the electrophilicity of the cyclic carbonate carbon, thereby enhancing its reactivity toward amines while maintaining the NCO-free formulation that reduces toxicological risks.
Solution Approach 2:
The invention creates a composite molecular structure combining cyclic carbonate groups with electron-withdrawing groups (ester or ether moieties) in a specific spatial arrangement. This composite structure leverages the electrophilic character of the cyclic carbonate and the electron-withdrawing effect of the beta-positioned groups to achieve enhanced reactivity without compromising the safety benefits of isocyanate-free systems.
2Object-affected harmful factors
If conventional cyclic carbonates are used to form NCO-free polyurethanes, then toxicological risks are reduced, but molecular weight is low
Solution Approach 1:
The patent modifies the cyclic carbonate structure by introducing electron-withdrawing groups (such as ester or ether moieties) at the beta position relative to the cyclic carbonate group. This structural parameter change increases the electrophilicity of the cyclic carbonate carbon, thereby enhancing its reactivity toward amines while maintaining the NCO-free formulation that reduces toxicological risks.
Solution Approach 2:
The invention creates a composite molecular structure combining cyclic carbonate groups with electron-withdrawing groups (ester or ether moieties) in a specific spatial arrangement. This composite structure leverages the electrophilic character of the cyclic carbonate and the electron-withdrawing effect of the beta-positioned groups to achieve enhanced reactivity without compromising the safety benefits of isocyanate-free systems.
3Productivity
If electron withdrawing groups are incorporated in the beta position to enhance reactivity, then reactivity increases, but synthesis complexity increases
Solution Approach 1:
The patent divides the synthesis into distinct stages: first forming the adduct of glycerine carbonate with the anhydride, then reacting this adduct with the polyepoxide compound. This segmentation of the synthesis process allows for better control of each reaction step and simplifies the overall procedure despite the introduction of electron-withdrawing groups.
Solution Approach 2:
The invention employs an intermediate adduct structure formed from glycerine carbonate and anhydride before the final reaction with polyepoxide. This intermediate serves as a mediator that facilitates the incorporation of electron-withdrawing groups in a controlled manner, reducing synthesis complexity compared to direct incorporation methods.
4Ease of manufacture
If conventional synthesis methods are used, then synthesis is simpler, but manufacturing cost is high and industrial feasibility is limited
Solution Approach 1:
The patent divides the synthesis into distinct stages: first forming the adduct of glycerine carbonate with the anhydride, then reacting this adduct with the polyepoxide compound. This segmentation of the synthesis process allows for better control of each reaction step and simplifies the overall procedure despite the introduction of electron-withdrawing groups.
Solution Approach 2:
The invention employs an intermediate adduct structure formed from glycerine carbonate and anhydride before the final reaction with polyepoxide. This intermediate serves as a mediator that facilitates the incorporation of electron-withdrawing groups in a controlled manner, reducing synthesis complexity compared to direct incorporation methods.
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 provides a cost-effective and industrially feasible synthesis of high molecular weight cyclic carbonate functional polyesters, reducing toxicological risks and improving the performance of coatings, adhesives, and sealants by increasing reactivity and molecular weight.
Implementation Method 1
reacting glycerine carbonate with an anhydride to form an adduct
Implementation Method 2
reacting the adduct with at least one polyepoxide compound to form the cyclic carbonate functional polyester
Implementation Method 3
enhancing reactivity and molecular weight through electron withdrawing groups in the beta position
Data Source
AI summary
The present application is directed to a method for preparing a cyclic carbonate functional polyester, said method comprising: reacting glycerine carbonate with an anhydride to form an Adduct (A); and, reacting said Adduct (A) with at least one polyepoxide compound to form said cyclic carbonate functional polyester (CC-PES). More particularly, the present application is directed to a method for preparing a cyclic carbonate functional polyester, said method comprising the stages: A) reacting glycerine carbonate with an anhydride to form an Adduct (A); B) providing a polycarboxylic acid; C) reacting said polycarboxylic acid with at least one diglycidyl ether to form an epoxy functional polyester; and, D) reacting said epoxy functional polyester with said Adduct (A) to form said cyclic carbonate functional polyester.