Crosslinked Polymers with N-Sulfonyldicarboximide Amine Capture
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Solution Overview
Problem
Existing polymeric surfaces with amine reactive functional groups, such as N-acyloxysuccinimide and azlactone, face challenges like rapid hydrolysis and difficulty in synthesizing azlactone linked to polymerizable groups, leading to inefficient immobilization of amine-containing materials.
Innovation Solution
The development of crosslinked polymeric materials with pendant N-sulfonyldicarboximide groups, formed from reaction mixtures containing amine capture monomers and crosslinking monomers with (meth)acryloyl groups, which react with amine-containing materials through a ring-opening reaction.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If N-acyloxysuccinimide functional groups are used on polymeric surfaces, then amine-containing materials can be immobilized, but the functional groups undergo rapid hydrolysis in aqueous solutions causing incomplete or inefficient immobilization
Solution Approach 1:
The patent changes the chemical structure of the amine reactive functional group from N-acyloxysuccinimide or azlactone to N-sulfonyldicarboximide. This structural parameter change results in a functional group that maintains high reactivity toward amine-containing materials while exhibiting improved hydrolytic stability in aqueous environments, thereby resolving the contradiction between immobilization efficiency and hydrolytic stability.
2Stability of the object's composition
If azlactone functional groups are used, then hydrolytic stability is improved, but it is difficult to synthesize azlactone linked to polymerizable groups other than vinyl groups, resulting in polymeric material with the amine reactive functional group directly attached to the polymer backbone making it difficult for amine containing material to get close enough for efficient immobilization
Solution Approach 1:
The patent employs N-sulfonyldicarboximide groups that can be linked to various polymerizable groups (not limited to vinyl groups), providing flexibility in synthesis. This allows the amine reactive functional group to be positioned at the end of a side chain rather than directly on the backbone, facilitating easier access for amine-containing materials while maintaining hydrolytic stability.
Solution Approach 2:
The patent introduces a separable structure where the amine reactive functional group (N-sulfonyldicarboximide) is positioned at the end of a side chain formed by polymerizable groups. This segmentation separates the hydrolytically stable functional group from the polymer backbone, allowing amine-containing materials to access the reactive group more easily through the side chain structure.
3Ease of manufacture
If amine reactive functional groups are directly attached to the polymer backbone, then synthesis is simplified, but the distance between amine containing material and amine reactive group is too great for efficient immobilization
Solution Approach 1:
The patent segments the polymeric structure into a backbone and pendant side chains, positioning the amine reactive functional group at the end of the side chain. This allows the functional group to be accessible to amine-containing materials while maintaining a relatively simple synthesis approach through standard polymerization methods.
Solution Approach 2:
The patent transitions from a two-dimensional attachment (direct backbone attachment) to a three-dimensional configuration where the functional group is positioned at the end of a side chain protruding from the backbone. This dimensional change creates spatial accessibility for amine-containing materials to reach the reactive group efficiently.
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 crosslinked polymeric materials with pendant N-sulfonyldicarboximide groups provide improved hydrolytic stability and efficient immobilization of amine-containing materials, enabling effective use in aqueous systems for applications like medical diagnosis and biological separations.
Implementation Method 1
The amine capture groups include N-sulfonyldicarboximide groups that can react with amine-containing materials by a ring opening reaction
Implementation Method 2
a crosslinking monomer that includes at least two (meth)acryloyl groups
Data Source
AI summary
Crosslinked polymeric materials are described that contain pendant amine capture groups. The amine capture groups include N-sulfonyldicarboximide groups that can react with amine-containing materials by a ring opening reaction. Reaction mixtures used to prepare the crosslinked polymeric materials, articles containing the crosslinked polymeric materials, methods of making articles, and methods of immobilizing an amine-containing material are also described.