Bis(hydroxyalkyl)mercaptosuccinates for Reversible Polymer Crosslinking
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Solution Overview
Problem
There is a need for mercapto succinic acids and derivatives that are useful in polymerization, particularly for synthesizing bioresorbable polymers and hydrogels with reversible crosslinking properties, as well as applications in hair treatments and heavy metal scavenging.
Innovation Solution
The development of compounds with specific functional groups, such as bis(hydroxyalkyl)mercaptosuccinates, which can be used to produce polymers and copolymers with thiol pendant groups, allowing for reversible crosslinking through disulfide linkages, and can be synthesized using various esterification reaction conditions and catalysts.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If mercapto succinic acid derivatives are used for polymer cross-linking, then reversible crosslinking properties are achieved, but the complexity of synthesizing specific derivatives increases
Solution Approach 1:
The synthesis is divided into modular steps: (1) protecting the thiol group as thioester, (2) esterifying hydroxyl groups with diols, (3) deprotecting thiol group. This segmentation allows independent optimization of each step and simplifies the overall synthesis of complex derivatives
Solution Approach 2:
The thiol group is protected as a thioester before esterification reactions. This preliminary protection prevents unwanted side reactions and enables selective modification of hydroxyl groups, simplifying the synthesis of derivatives with specific functional groups
2Adaptability or versatility
If a wide variety of mercapto succinic acid derivatives are synthesized, then application versatility is improved, but the manufacturing complexity increases
Solution Approach 1:
A universal synthesis platform is established using mercapto succinic acid as core substrate, which can be derivatized with various diols (ethylene glycol, propylene glycol, butylene glycol, etc.) to produce derivatives suitable for different applications including bioresorbable polymers, hydrogels, and metal scavenging materials
Solution Approach 2:
Systematic variation of parameters including diol chain length, diol structure (linear/branched), and substitution patterns allows tuning of derivative properties for specific applications while maintaining a consistent synthesis methodology
3Manufacturing precision
If specific esterification conditions and catalysts are used, then manufacturing precision is improved, but the ease of manufacture decreases
Solution Approach 1:
Thioester intermediates are used to protect and activate the thiol group during esterification. This intermediary approach enables precise control of reaction selectivity while using standard esterification catalysts, balancing manufacturing precision with ease of manufacture
Solution Approach 2:
Chemical protection groups (thioesters) replace the need for complex mechanical or physical control methods to achieve selectivity. The chemical methodology provides precise control through molecular recognition and reactivity patterns rather than process engineering
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
These compounds enable the production of biocompatible polymers and copolymers with a wide range of physical properties, including clear and colorless films, and can be used in applications such as tissue scaffolds, adhesives, and oxygen scrubbers, with the ability to form reversible disulfide linkages for controlled degradation.
Implementation Method 1
They can be readily crosslinked using an oxidizing agent or via a free radical reaction to form a disulfide linkage
Implementation Method 2
The disulfide linkage can be reversibly cleaved, for example, by using a reducing agent
Implementation Method 3
They also may find use in applications such as 'permanent' type hair treatments or as metal scavengers
Data Source
AI summary
The present invention provides bis(hydroxyalkyl)mercaptosuccinates of the formula:and derivatives thereof, where X1, X2, Z1, Z2, Y1, Y2, Ra, Rb, R1, and R2 are those defined herein. The present invention also provides methods for producing and using the same.