Polyhydroxyurethane Synthesis Using CO2 and Dimer Acid for Safer Adhesives

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Solution Overview

Problem

Conventional polyurethane production is hazardous due to the use of toxic materials like isocyanate and phosgene, necessitating a safe and eco-friendly alternative.

Innovation Solution

A method for preparing polyhydroxyurethane using vegetable oil-derived dimer acid and carbon dioxide, involving steps of dimer acid diglycidyl ester formation, dimer acid dicyclic carbonate synthesis, and polyhydroxyurethane preparation through diamine reaction.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional polyurethane production using isocyanate and phosgene is used, then polyurethane can be produced efficiently, but the process becomes hazardous and toxic

Engineering Contradiction:
Improvepolyurethane production efficiencyVSAvoidtoxicity and hazard from isocyanate and phosgene
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent extracts and eliminates the harmful isocyanate component from the polyurethane synthesis process. Instead of using isocyanate as a starting material, the invention uses amine and carbon dioxide, removing the toxic substance while maintaining the ability to produce polyurethane polymers through an alternative chemical pathway.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent converts carbon dioxide, a greenhouse gas and waste product, into a useful chemical intermediate (cyclic carbonate) that serves as a building block for polyurethane synthesis. This transforms an environmental harm into a beneficial raw material, simultaneously reducing CO2 emissions and eliminating toxic isocyanate usage.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

2Object-affected harmful factors

If polyhydroxyurethane is synthesized through polyaddition reaction of cyclic carbonates and amines, then eco-friendly production is achieved, but the process complexity increases

Engineering Contradiction:
Improveenvironmental friendliness and safetyVSAvoidsynthesis process complexity
Core Design Contradiction:
Object-affected harmful factorsVSDevice complexity

Solution Approach 1:

The patent divides the polyurethane synthesis process into distinct sequential steps: (1) synthesis of cyclic carbonate from amine and CO2, (2) polyaddition reaction of cyclic carbonate with diamine to form polyhydroxyurethane. This segmentation allows each step to be optimized independently and facilitates control over the synthesis process while maintaining eco-friendly conditions.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent performs preliminary synthesis of cyclic carbonate intermediates before the main polyaddition reaction. This preliminary action prepares the reactive intermediate in advance, allowing better control over the subsequent polymerization step and enabling optimization of each stage separately, thereby managing overall process complexity.

Inventive Principle:
Principle #10Preliminary action

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 method produces eco-friendly polyhydroxyurethane with enhanced chemical resistance and physical properties, suitable for use in pressure-sensitive adhesives with adhesive properties.

Implementation Method 1

Polyhydroxyurethane [poly (hydroxy urethane), PHU], a type of non-isocyanate polyurethane (NIPU), may be synthesized through a polyaddition reaction of cyclic carbonates and amines. The cyclic carbonates may be synthesized by inserting carbon dioxide (CO2) into epoxy resin.

Methodology Applied
Scientific EffectPolyaddition reaction:

Implementation Method 2

Polyhydroxyurethane [poly (hydroxy urethane), PHU], a type of non-isocyanate polyurethane (NIPU), may be synthesized through a polyaddition reaction of cyclic carbonates and amines.

Methodology Applied
Scientific EffectPolyaddition reaction:

Implementation Method 3

the polyhydroxyurethane has a hydroxyl group, which induces additional hydrogen bonding in addition to hydrogen bonding between urethane groups, thereby enhancing chemical resistance and physical properties

Methodology Applied
Scientific EffectHydrogen bonding:

Data Source

PatentUS12486361B2Method for preparing polyhydroxyurethane, polyhydroxyurethane prepared using the method and pressure-sensitive adhesive comprising the polyhydroxyurethane
Publication Date: 2025.12.02 KOREA RES INST OF CHEM TECH
  • US12486361B2 patent drawing
  • US12486361B2 patent drawing
  • US12486361B2 patent drawing

AI summary

Provided are a method for preparing polyhydroxyurethane, polyhydroxyurethane prepared using the method and a pressure-sensitive adhesive comprising the polyhydroxyurethane. According to the present disclosure, it is possible to prepare polyhydroxyurethane in an eco-friendly manner using vegetable oil-derived dimer acid and carbon dioxide and to provide a pressure-sensitive adhesive including the polyhydroxyurethane.