Cyclic Monothiocarbonate Ring Opening for Low-Byproduct Polycarbonates

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Solution Overview

Problem

Existing methods for synthesizing polymers with carbonate groups and sulfur-containing functional groups face challenges such as the need for high temperatures, the production of condensation by-products like water or alcohol, and the lack of easy modification or crosslinking capabilities.

Innovation Solution

A process involving the reaction of a compound with a five-membered cyclic monothiocarbonate group with a hydroxy group to form non-cyclic carbonate groups, which can be further modified by reacting with a compound containing a thiol group, using moderate temperatures and avoiding condensation by-products.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional methods are used to synthesize polymers with carbonate groups and sulfur-containing functional groups, then the polymers can be obtained, but high temperatures are required and condensation by-products like water or alcohol are produced

Engineering Contradiction:
Improvepolymer synthesis reliabilityVSAvoidcondensation by-products
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The invention extracts and eliminates the harmful condensation by-products (water or alcohol) from the synthesis process by using a ring-opening reaction mechanism instead of conventional condensation polymerization. The cyclic monothiocarbonate ring opens upon reaction with hydroxy groups, directly forming the desired polymer structure without generating condensate by-products.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention changes the reaction parameters by using moderate temperatures instead of high temperatures required by conventional methods. The ring-opening reaction of cyclic monothiocarbonates proceeds efficiently at moderate temperatures, eliminating the need for high-temperature processing while avoiding by-product formation.

Inventive Principle:
Principle #35Parameter changes

2Quantity of substance

If conventional high-temperature synthesis methods are used, then polymers with carbonate groups can be obtained, but the process requires high temperatures and produces condensation by-products

Engineering Contradiction:
Improvepolymer production efficiencyVSAvoidsynthesis temperature
Core Design Contradiction:
Quantity of substanceVSTemperature

Solution Approach 1:

The invention fundamentally changes the temperature parameter by utilizing a ring-opening reaction mechanism that proceeds at moderate temperatures. The chemical reactivity of the cyclic monothiocarbonate ring allows the reaction to occur efficiently without requiring high-temperature conditions, thus reducing energy consumption and avoiding thermal degradation.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If polymers are synthesized with functional groups, then the polymers have desired properties, but the functional groups do not easily undergo chemical reactions for modification or crosslinking

Engineering Contradiction:
Improvepolymer property stabilityVSAvoidchemical reactivity for modification
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The invention introduces specific reactive functional groups (thiol groups and unsaturated bonds) at localized positions within the polymer structure. These groups are strategically incorporated during synthesis to maintain overall polymer stability while providing specific sites that are highly reactive for subsequent modification and crosslinking reactions.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The invention creates polymers with multi-functional groups that serve multiple purposes: the carbonate groups provide structural stability and desired material properties, while the thiol groups and unsaturated bonds provide reactive sites for various chemical modifications, crosslinking reactions, and further functionalization, making the polymer universally adaptable for different applications.

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 method allows for the production of polymers with improved mechanical, optical, and chemical properties, enabling easy modification and crosslinking, and results in transparent, thermally stable polymers suitable for various applications including coatings, adhesives, and mold formation.

Implementation Method 1

a compound A) comprising at least one five-membered cyclic monothiocarbonate group is reacted with at least one hydroxy group of a compound B) or of compound A) itself

Methodology Applied
Scientific EffectRing-opening reaction: Chemical Bonding

Data Source

PatentUS12365760B2Process for the synthesis of polycarbonates from cyclic monothiocarbonates
Publication Date: 2025.07.22 BASF SE
  • US12365760B2 patent drawing
  • US12365760B2 patent drawing
  • US12365760B2 patent drawing

AI summary

A process can be used for the synthesis of compounds containing at least one non-cyclic carbonate group, wherein a compound A) containing at least one five-membered cyclic monothiocarbonate group is reacted with at least one hydroxy group of a compound B) or of compound A) itself.