Dendrimeric Substrate via Azlactone Ring-Opening

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Solution Overview

Problem

There is a scarcity of effective methods for covalently bonding dendrimeric materials to substrates, limiting their application in separation and purification processes, as existing approaches often result in fewer reactive end groups due to steric constraints and inefficiencies in attaching previously prepared dendrimeric materials.

Innovation Solution

The development of methods involving azlactone-functional substrates and nucleophilic compounds to form dendrimeric structures through ring-opening reactions, allowing for the creation of dendrimeric materials with reactive end groups that can be extended and branched, thereby enhancing their functionality and attachment to substrates.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If previously prepared dendrimeric materials are adhered to substrates, then attachment to substrate is achieved, but the number of reactive end groups is reduced due to steric constraints and inefficiencies

Engineering Contradiction:
Improveattachment effectivenessVSAvoidnumber of reactive end groups
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

Instead of attaching pre-formed dendrimers to substrates (conventional approach), the invention inverts the process by first attaching a small core to the substrate and then growing the dendrimeric structure outward from that anchored core. This allows the dendrimer to self-assemble in solution, avoiding steric constraints that would occur if a large pre-formed dendrimer tried to attach to the substrate surface. The result is maximum retention of reactive end groups while achieving secure substrate attachment.

Inventive Principle:
Principle #13The other way round (Inversion)

Solution Approach 2:

The invention performs preliminary action by first attaching a small core structure to the substrate before dendrimer growth. This pre-positioned core serves as a foundation that directs subsequent dendrimer assembly, ensuring proper orientation and maximizing the number of reactive end groups that can be exposed and accessible for further functionalization.

Inventive Principle:
Principle #10Preliminary action

2Reliability

If dendrimeric materials are covalently bonded to substrates, then stability of attachment is improved, but the complexity of the bonding process increases

Engineering Contradiction:
Improveattachment stabilityVSAvoidbonding process complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The invention segments the dendrimer formation process into distinct stages: (1) attachment of a small core to the substrate, (2) growth of dendrimeric branches from the core in solution, and (3) functionalization of the resulting structure. This segmentation simplifies each individual step while achieving the overall goal of stable covalent bonding with high reactive end group retention.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The small core structure serves as an intermediary between the substrate and the growing dendrimeric branches. It provides a stable attachment point to the substrate while simultaneously serving as a platform for controlled dendrimer assembly in solution, thereby mediating between the requirements for stable attachment and simplified processing.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Quantity of substance

If dendrimeric structures are extended and branched using divergent process, then the number of reactive end groups increases, but the manufacturing complexity increases

Engineering Contradiction:
Improvenumber of reactive end groupsVSAvoidmanufacturing simplicity
Core Design Contradiction:
Quantity of substanceVSEase of manufacture

Solution Approach 1:

The divergent dendrimer growth process is made self-service by allowing the dendrimeric branches to self-assemble from small molecules in solution around the anchored core. The chemical reactivity and steric arrangement automatically direct the formation of the dendrimeric structure with the correct geometry and maximum number of reactive end groups, eliminating the need for complex manual assembly or precise positioning operations.

Inventive Principle:
Principle #25Self-service

Solution Approach 2:

The invention controls dendrimer growth by changing parameters such as the choice of core structure, the nature of the dendrimer building blocks, the solvent conditions, and the reaction temperature. By optimizing these parameters, the divergent growth process becomes highly efficient and controllable, producing dendrimeric structures with desired properties while maintaining manufacturing simplicity.

Inventive Principle:
Principle #35Parameter changes

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 enables the formation of dendrimeric structures with increased reactive end groups and branching, improving their utility in separation and purification processes, such as ion exchange and affinity capture, by effectively bonding dendrimeric materials to substrates, thereby enhancing their functional capabilities.

Implementation Method 1

reacting an azlactone group on the substrate with a first nucleophilic compound having multiple nucleophilic groups to form a substrate-attached nucleophilic compound

Methodology Applied
Scientific EffectRing-opening reaction: Chemical Bonding

Implementation Method 2

reacting the nucleophilic end group of the substrate-attached nucleophilic compound with a first azlactone compound having multiple azlactone groups to form a first dendrimeric structure

Methodology Applied
Scientific EffectRing-opening reaction: Chemical Bonding

Data Source

PatentUS7556858B2Substrate with attached dendrimers
Publication Date: 2009.07.07 SOLVENTUM INTELLECTUAL PROPERTIES CO
  • US7556858B2 patent drawing
  • US7556858B2 patent drawing
  • US7556858B2 patent drawing

AI summary

Articles and methods of making articles are provided. The articles have a dendrimeric material attached to a substrate. The dendrimeric material, an attachment group connecting the dendrimeric material to the substrate, or both the dendrimeric material and the attachment group can be formed by a ring-opening reaction of an azlactone group with a nucleophilic group such as a hydroxyl group, primary amino group, or secondary amino group.