Mixed Cyclohexanetripropionic Esters for Low-Volatility PVC Plasticizers

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Solution Overview

Problem

Trimethyl esters of 1,2,4-cyclohexanetripropionic acid exhibit high viscosity and significant evaporation during processing, leading to suboptimal performance as plasticizers in PVC-based plastisols.

Innovation Solution

A mixture of triesters of 1,2,4-cyclohexanetripropionic acid is formulated with 5 to 75 mol% methyl groups and 25 to 95 mol% C2 to C10 alkyl groups, particularly C4 to C9 alkyl groups, prepared by transesterification, to enhance plasticizing properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If trimethyl esters of 1,2,4-cyclohexanetripropionic acid are used as plasticizers, then the plasticizer can be applied in PVC-based plastisols, but the plastisol exhibits high viscosity and significant evaporation during processing

Engineering Contradiction:
Improveplasticizer performanceVSAvoidhigh viscosity and evaporation
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent changes the chemical structure parameters of the plasticizer by replacing some methyl groups with longer alkyl chains (C2-C10, preferably C4-C9). This structural modification alters the physical properties, specifically reducing viscosity and evaporation tendency while maintaining plasticizing effectiveness in PVC plastisols.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite plasticizer system by combining 1,2,4-cyclohexanetripropionic acid with mixed alkyl groups (methyl plus longer chains). This composite structure leverages the benefits of different chain lengths to achieve both low gelling temperature and reduced evaporation, resolving the contradiction between plasticizer effectiveness and processing stability.

Inventive Principle:
Principle #40Composite materials

2Temperature

If trimethyl esters are used as plasticizers, then they provide low gelling temperature, but they exhibit significant evaporation during processing

Engineering Contradiction:
Improvegelling temperatureVSAvoidevaporation
Core Design Contradiction:
TemperatureVSLoss of substance

Solution Approach 1:

The patent modifies the molecular weight and chain length parameters of the plasticizer by introducing C2-C10 alkyl groups (preferably C4-C9) alongside methyl groups. This parameter change increases molecular weight to reduce evaporation while the specific arrangement maintains low gelling temperature through the cyclohexane core structure.

Inventive Principle:
Principle #35Parameter changes

3Adaptability or versatility

If trimethyl esters of 1,2,4-cyclohexanetripropionic acid are used as plasticizers, then they can function in plastisol formulations, but the plastisol exhibits relatively high viscosity

Engineering Contradiction:
Improveplasticizer applicabilityVSAvoidviscosity
Core Design Contradiction:
Adaptability or versatilityVSStress or pressure

Solution Approach 1:

The patent changes the molecular structure parameters by replacing some short methyl groups with longer C2-C10 alkyl chains. This structural modification reduces the overall viscosity of the plastisol formulation while the mixed ester composition maintains compatibility and adaptability across different PVC-based applications.

Inventive Principle:
Principle #35Parameter changes

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 mixed esters improve processing stability and reduce evaporation, offering better application-related properties in plasticizer compositions.

Implementation Method 1

a significant portion of the trimethyl ester would evaporate during processing and thus no longer remain in the final product

Methodology Applied
Scientific EffectEvaporation: Evaporation

Implementation Method 2

prepared by transesterification

Methodology Applied
Scientific EffectTransesterification: Chemical Bonding

Data Source

PatentEP4703348A1Mixed esters of 1,2,4-cyclohexanetripropionic acid and a plasticizer composition containing the mixed esters
Publication Date: 2026.03.04 EVONIK OXENO GMBH & CO KG
  • EP4703348A1 patent drawing
  • EP4703348A1 patent drawing
  • EP4703348A1 patent drawing

AI summary

The present invention relates to a plasticizer composition comprising a compound of formula (1) and at least one dialkyl terephthalic acid ester, wherein the two alkyl groups in the dialkyl terephthalic acid ester each have 8 or 9 carbon atoms.