Cyclohexane Dicarboxylate Mixed Ester Plasticizers for Low Volatility

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Solution Overview

Problem

Current non-phthalate plasticizers, such as bis(2-ethylhexyl) terephthalate (DOTP), do not provide adequate fusion capability and viscosity performance in polymer plasticizer systems, and are more volatile than aromatic counterparts.

Innovation Solution

A novel mixed cyclohexane dicarboxylate ester (MCHDE) composition comprising specific weight percentages of compounds of formula I, II, and III, which enhance fusion capability and reduce volatility.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If DOTP is used as a non-phthalate plasticizer, then it provides reasonable plasticizer performance, but it does not have acceptable fusion capability and is more volatile than aromatic counterparts

Engineering Contradiction:
Improvefusion capabilityVSAvoidvolatility
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent changes the chemical structure parameters of the plasticizer by using cyclohexane dicarboxylate esters instead of aromatic esters, and by controlling the alkyl chain lengths (C1-C6) and their distribution. This structural parameter change reduces volatility while improving fusion capability, as the cyclic aliphatic structure provides better thermal stability and fusion characteristics compared to aromatic structures.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs a composite plasticizer composition containing multiple cyclohexane dicarboxylate ester compounds with different alkyl chain configurations (Formula I, II, and III compounds). This composite approach combines the advantages of different molecular structures to achieve both low volatility and excellent fusion capability, overcoming the limitations of single-component plasticizers like DOTP.

Inventive Principle:
Principle #40Composite materials

2Stability of the object's composition

If DOTP is used as a non-phthalate plasticizer, then it is available as a general purpose plasticizer, but it does not have acceptable viscosity performance in polymer plasticizer systems

Engineering Contradiction:
Improveviscosity performanceVSAvoidcompatibility with legacy production processes
Core Design Contradiction:
Stability of the object's compositionVSAdaptability or versatility

Solution Approach 1:

The patent optimizes the viscosity performance by carefully selecting and combining cyclohexane dicarboxylate ester compounds with specific alkyl chain lengths (C1-C6). The distribution of different chain lengths and the cyclic structure provide optimal viscosity characteristics that maintain stability in polymer plasticizer systems, improving upon DOTP's viscosity performance while maintaining compatibility with existing production processes.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If cyclohexane dicarboxylate esters are used to improve fusion capability, then fusion performance is enhanced, but the composition complexity increases

Engineering Contradiction:
Improvefusion capabilityVSAvoidcomposition complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent uses a composite of three types of cyclohexane dicarboxylate ester compounds (Formula I, II, and III) with specific weight percentage ranges. This composite structure achieves enhanced fusion capability by combining different molecular configurations, while the defined composition ranges prevent excessive complexity by providing clear formulation guidelines for manufacturing.

Inventive Principle:
Principle #40Composite materials

Data Source

PatentEP3990531B1Cyclohexane dicarboxylate mixed ester compositions useful as plasticizers
Publication Date: 2025.12.10 EASTMAN CHEM CO
  • EP3990531B1 patent drawing
  • EP3990531B1 patent drawing
  • EP3990531B1 patent drawing

AI summary

The present application discloses novel cyclohexane dicarboxylate mixed esters of formula I: wherein R1, R2, and n are defined herein. The mixed esters are useful as plasticizers. The application also discloses resin compositions comprising the cyclohexane dicarboxylate mixed esters of formula I.