Crosslinked Poly(beta-amino esters) for Tunable Degradation

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Solution Overview

Problem

The development of biodegradable and biocompatible polymers with diverse properties for applications in drug delivery, tissue engineering, and biomaterials is hindered by the complexity of synthesizing multifunctional macromers, which often requires multiple functionalization and purification steps, making it difficult to predict desirable properties such as degradation and mechanics from chemical and structural details.

Innovation Solution

Cross-linked polymeric materials are prepared through free radical-initiated or photo-crosslinking of poly(beta-amino esters), allowing for the creation of materials with varied properties such as biodegradability, biocompatibility, and mechanical strength by controlling the composition of starting materials and crosslinking processes.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If multifunctional macromers are synthesized through multiple functionalization and purification steps, then diverse polymer properties can be achieved, but the synthesis complexity and time increase significantly

Engineering Contradiction:
Improvepolymer property diversityVSAvoidsynthesis process complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The synthesis process is segmented into two distinct stages: first, poly(beta-amino esters) are synthesized with biodegradable and biocompatible properties; second, these polymers are functionalized with photopolymerizable groups to enable crosslinking. This segmentation allows each stage to be optimized independently, reducing overall complexity while maintaining property diversity.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The poly(beta-amino esters) are prepared in advance with controlled degradation and mechanical properties, then these pre-synthesized polymers are directly functionalized with photopolymerizable groups. This preliminary action eliminates the need for multiple sequential functionalization steps, significantly simplifying the synthesis pathway.

Inventive Principle:
Principle #10Preliminary action

2Manufacturing precision

If multiple functionalization steps are performed to achieve desired polymer properties, then property prediction becomes more accurate, but the number of purification steps increases

Engineering Contradiction:
Improveproperty prediction accuracyVSAvoidpurification time
Core Design Contradiction:
Manufacturing precisionVSLoss of time

Solution Approach 1:

The invention changes the chemical parameters of the starting materials - specifically using poly(beta-amino esters) with controlled molecular weight, degradation rate, and biocompatibility - and then applies a single functionalization step with photopolymerizable groups. This parameter change approach allows property prediction based on initial polymer characteristics without requiring multiple purification cycles.

Inventive Principle:
Principle #35Parameter changes

3Adaptability or versatility

If conventional synthesis methods are used for photopolymerizable precursors, then diverse material properties can be obtained, but the synthesis efficiency decreases

Engineering Contradiction:
Improvematerial property rangeVSAvoidsynthesis efficiency
Core Design Contradiction:
Adaptability or versatilityVSProductivity

Solution Approach 1:

The poly(beta-amino esters) serve multiple functions: they provide the base polymer structure with biodegradability, biocompatibility, and controlled mechanical properties, and also serve as the scaffold for attaching photopolymerizable groups. This multi-functionality eliminates the need for separate synthesis of different precursor types, significantly improving synthesis efficiency while maintaining material property diversity.

Inventive Principle:
Principle #6Universality (Multi-functionality)

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 efficient preparation of materials with tailored properties for drug delivery, tissue engineering, and other applications, offering a wide range of degradation profiles and mechanical properties, simplifying the synthesis process and eliminating the need for additional purification steps.

Implementation Method 1

Cross-linked polymeric materials are prepared by the free radical (e.g., photocrosslinking, thermal initiation) initiated cross-linking of poly(beta-amino esters)

Methodology Applied
Scientific EffectFree radical initiation:

Implementation Method 2

The photoinitiator is used in the crosslinking reaction

Methodology Applied
Scientific EffectPhotoinitiation: Photopolymerisation

Implementation Method 3

The poly(beta-amino esters) include a hydrolysable ester linkage

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Data Source

PatentUS8808681B2Crosslinked, degradable polymers and uses thereof
Publication Date: 2014.08.19 MASSACHUSETTS INST OF TECH
  • US8808681B2 patent drawing
  • US8808681B2 patent drawing
  • US8808681B2 patent drawing

AI summary

Acrylate-terminated poly(beta-amino esters) are cross-linked to form materials useful in the medical as well as non-medical field. The polymeric starting material is combined with a free radical initiator, either a thermal initiator or a photoinitiator, and the mixture for cross-linking is heated or exposed to light depending on the initiator used. The resulting materials due to the hydrolysable ester bond in the polymer backbone are biodegradable under physiological conditions. These cross-linked materials are particular useful as drug delivery vehicles, tissue engineering scaffolds, and in fabricating microdevices. The materials may also be used as plastics, coating, adhesives, inks, etc. The cross-linked materials prepared exhibit a wide range of degradation times, mass loss profiles, and mechanical properties. Therefore, the properties of the material may be tuned for the desired use. The high-throughput approach to preparing a library of cross-linked poly(beta-amino esters) allows for the rapid screening and design of degradable polymers for a variety of applications.