Crosslinked Polycarbonate Nanoparticles for Drug Delivery

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Solution Overview

Problem

The introduction of side-chain functional groups in degradable polymers, such as poly(ester)s and poly(carbonate)s, is challenging, limiting their applicability in advanced applications, and existing polymers exhibit slower degradation profiles with less toxic byproducts, making them less effective for nanomaterials.

Innovation Solution

The development of crosslinked allyl and epoxy functionalized polycarbonates through intermolecular crosslinking processes using thiolene-click and epoxide-amine reactions, resulting in nanoscopic particles with controlled sizes and architectural nature, suitable for nanosponges and drug delivery systems.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If side-chain functional groups are introduced in degradable polymers, then applicability in advanced applications is improved, but the complexity of polymer synthesis increases

Engineering Contradiction:
Improveapplicability in advanced applicationsVSAvoidcomplexity of polymer synthesis
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent incorporates functional groups (allyl and epoxy) directly into the polymer backbone during the ring-opening polymerization process, rather than introducing them afterward through complex post-synthesis modifications. This preliminary incorporation simplifies the overall synthesis pathway while maintaining the versatility needed for advanced applications such as nanomaterials and drug delivery systems.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent creates polymers with specific local functional groups (allyl or epoxy) positioned along the polymer chain, enabling targeted chemical reactions at specific locations. This local functionalization allows the polymer to exhibit diverse properties and reactivities appropriate for different advanced applications without requiring complex global structural modifications.

Inventive Principle:
Principle #3Local quality

2Manufacturing precision

If crosslinked polycarbonates are formed through intermolecular crosslinking, then nanoscopic particles with controlled sizes are produced, but the complexity of the manufacturing process increases

Engineering Contradiction:
Improvecontrolled sizes of nanoscopic particlesVSAvoidcomplexity of manufacturing process
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent employs small molecule crosslinkers (such as diamines for epoxy groups or thiols for allyl groups) as intermediaries to bridge polymer chains and form crosslinked networks. These crosslinkers mediate the formation of nanoscopic particles with controlled sizes by controlling the crosslinking density and network structure, while keeping the manufacturing process relatively simple through well-established chemical reactions.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent controls particle size and morphology by adjusting parameters such as crosslinker-to-polymer ratio, reaction temperature, and solvent conditions. By systematically varying these parameters, the manufacturing process achieves precise control over nanoscopic particle dimensions without requiring complex equipment or multi-step procedures.

Inventive Principle:
Principle #35Parameter changes

3Duration of action of moving object

If poly(ester)s are used for degradation, then degradation occurs, but the degradation profile is slow and byproducts are more toxic

Engineering Contradiction:
Improvedegradation rateVSAvoidtoxicity of byproducts
Core Design Contradiction:
Duration of action of moving objectVSObject-generated harmful factors

Solution Approach 1:

The patent changes the chemical composition parameter from poly(ester) to poly(carbonate) backbone structures. This fundamental parameter change results in both faster degradation rates and the formation of less toxic byproducts (carbon dioxide and alcohols instead of carboxylic acids), thereby simultaneously improving both aspects of the contradiction.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite structures combining polycarbonate backbones with pendant functional groups (allyl or epoxy) that can further react or degrade. This composite approach allows the material to exhibit enhanced degradation properties compared to simple poly(esters), achieving both faster degradation and reduced toxicity through the carbonate linkage chemistry.

Inventive Principle:
Principle #40Composite materials

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 functionalized poly(carbonate) particles with controlled sizes and properties, enhancing their applicability in nanomaterials and drug delivery systems by providing a controlled release mechanism and improved biocompatibility.

Implementation Method 1

crosslinking the first and second allyl functionalized polycarbonate via a crosslinker

Methodology Applied
Scientific EffectThiolene-click reaction: Chemical Bonding

Implementation Method 2

crosslinking the first and second epoxy functionalized polycarbonate via a crosslinker

Methodology Applied
Scientific EffectEpoxide-amine reaction: Chemical Bonding

Implementation Method 3

Poly(carbonate)s prepared by the ring-opening polymerization (ROP) of 6-membered cyclic monomers

Methodology Applied
Scientific EffectRing-opening polymerization: Chemical Bonding

Data Source

PatentUS11591443B2Polycarbonate containing compounds and methods related thereto
Publication Date: 2023.02.28 VANDERBILT UNIV
  • US11591443B2 patent drawing
  • US11591443B2 patent drawing
  • US11591443B2 patent drawing

AI summary

Disclosed herein are crosslinked polycarbonates, composition thereof and methods thereof. The crosslinked polycarbonates can be prepared from allyl or epoxy polycarbonates. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.