CBDO-1 Diol Polymers Replacing BPA

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Solution Overview

Problem

The development of polymers with thermal, mechanical, and optical properties similar to Bisphenol A (BPA) has been hindered by the carcinogenic and endocrine-disrupting effects of BPA, and existing semi-rigid cyclic monomers like 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD) are limited in reactivity and high molecular weight synthesis due to their production methods.

Innovation Solution

The synthesis of trans 1,3-cyclobutane dimethanol (CBDO-1), a semi-rigid diol with two rigid phenyl rings, which can be used to form polymers through dimerization and reduction of trans-cinnamic acid, offering higher reactivity and flexibility to introduce functional groups, thereby replacing BPA in polymer structures.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Strength

If BPA is used as a polymer precursor, then thermal and mechanical properties are improved, but carcinogenic and endocrine-disrupting effects occur

Engineering Contradiction:

Improvethermal and mechanical propertiesVSAvoidcarcinogenic and endocrine-disrupting effects

Core Design Contradiction:

StrengthVSObject-affected harmful factors

Solution Approach 1:

The patent extracts and removes the harmful phenolic groups from the polymer structure while retaining the beneficial thermal and mechanical properties through alternative non-phenolic chemical structures

Inventive Principle:

Principle #2Taking out (Extraction)

Solution Approach 2:

The patent employs readily available starting materials (cinnamic acid, cyclopentadienone) that can be easily synthesized and discarded, replacing the persistent harmful BPA structure with degradable alternatives

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

2Stability of the object's composition

If TMCD is used as a semi-rigid cyclic monomer, then polymer structure is formed, but reactivity is limited and high molecular weight synthesis is hindered

Engineering Contradiction:

Improvesemi-rigid cyclic structureVSAvoidreactivity and high molecular weight synthesis

Core Design Contradiction:

Stability of the object's compositionVSEase of manufacture

Solution Approach 1:

The patent changes the chemical parameters of the cyclic monomer by introducing reactive functional groups (vinyl, aldehyde, ketone) that enable higher reactivity and molecular weight synthesis while maintaining the semi-rigid cyclic structure

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent creates composite molecular structures combining the semi-rigid cyclic core with reactive functional groups, achieving both structural stability and chemical reactivity

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

CBDO-1-based polymers exhibit high thermal stability and increased glass transition temperatures, making them suitable replacements for BPA with reduced carcinogenic and endocrine-disrupting effects, while allowing for higher molecular weights and tunable properties.

Implementation Method 1

dimerizing trans-cinnamic acid, forming CBDA-1

Methodology Applied

Scientific EffectPhotocycloaddition: Photopolymerisation

Implementation Method 2

reducing CBDA-1, forming CBDO-1

Methodology Applied

Scientific EffectReduction: Reduction

Implementation Method 3

condensing CBDO-1 with a diacid, forming monomeric subunits

Methodology Applied

Scientific EffectCondensation: Condensation

Data Source

PatentUS11326054B2Polymers comprising 1,3-cyclobutane dimethanol (CBDO-1)

Publication Date: 2022.05.10 UNIVERSITY OF NORTH DAKOTA

AI summary

A polymer includes a plurality of repeated polymerized units according to scheme (2):