Diisononyl cyclohexanedicarboxylate plasticizer branching

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Solution Overview

Problem

The use of phthalates, particularly di-2-ethylhexyl phthalate (DEHP), as plasticizers in applications like medical articles and food contact materials poses health risks, necessitating the development of safer alternatives with similar performance properties.

Innovation Solution

The development of mixtures of diisononyl esters of 1,2-cyclohexanedicarboxylic acid with a degree of branching between 1.2 and 2.0, which can replace DEHP as plasticizers in PVC, offering similar or better cold flexibilization capacity and processing properties with minimal adaptation required.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If phthalates (DEHP) are used as plasticizers, then good plasticizing performance and processing properties are achieved, but health risks arise

Engineering Contradiction:
Improveplasticizing performanceVSAvoidhealth risks
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical structure parameters by replacing phthalate esters with alicyclic polycarboxylic esters (specifically diisononyl 1,2-cyclohexanedicarboxylate). This structural parameter change maintains the plasticizing performance while eliminating the health risks associated with phthalates, as the alicyclic structure provides similar plasticizing action without the harmful properties of aromatic phthalates.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs alicyclic polycarboxylic esters as temporary replacements for phthalates during the transition period. These esters serve as safe alternative plasticizers that can be easily introduced into existing formulations without requiring complete reformulation, providing a practical bridge between harmful phthalate usage and fully safe alternative plasticization systems.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

2Object-affected harmful factors

If alicyclic polycarboxylic esters are used to replace phthalates, then health safety is improved, but performance profile differs

Engineering Contradiction:
Improvehealth safetyVSAvoidperformance profile
Core Design Contradiction:
Object-affected harmful factorsVSReliability

Solution Approach 1:

The patent applies local quality by selectively optimizing specific properties of the alicyclic polycarboxylic ester. By controlling the degree of branching of the alcohol component (isononyl radicals with degree of branching from 1.2 to 2.0), the invention enhances cold flexibilization capacity and processing properties in specific areas while maintaining overall health safety benefits. This targeted optimization addresses specific performance gaps without compromising the fundamental health safety advantage.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent creates a composite plasticizer system by combining alicyclic polycarboxylic esters with specific alcohol components (isononyl radicals with controlled branching). This composite approach integrates the health safety benefits of alicyclic structures with the performance-enhancing properties of specifically branched alcohol chains, achieving a balanced performance profile that matches or exceeds phthalate performance while maintaining health safety.

Inventive Principle:
Principle #40Composite materials

3Reliability

If diisononyl cyclohexanedicarboxylates with specific branching are used, then cold flexibilization capacity is improved, but manufacturing complexity increases

Engineering Contradiction:
Improvecold flexibilization capacityVSAvoidmanufacturing complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent optimizes the degree of branching parameter of the isononyl radicals to fall within the specific range of 1.2 to 2.0. This parameter change enhances cold flexibilization capacity by controlling the molecular structure. The invention acknowledges that achieving this specific branching range may require adjusted manufacturing processes, but the performance improvement in cold flexibilization justifies the controlled complexity in alcohol component selection and synthesis.

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

These diisononyl cyclohexanedicarboxylates (DINCH) exhibit low viscosity in plastisols, low mass loss after thermal aging, and comparable processing properties to DEHP, making them suitable replacements with reduced health concerns.

Implementation Method 1

the ring hydrogenation of the corresponding aromatic polycarboxylic esters, for example of the abovementioned phthalates

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Implementation Method 2

over supported Pd catalysts doped with Ni, Pt and/or Ru, at temperatures greater than or equal to 140° C. and a pressure between 50 and 170 bar

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS7786201B2Mixture of diisononyl esters of 1,2-cyclohexanedicarboxylic acid, method for the production thereof and use of these mixtures
Publication Date: 2010.08.31 EVONIK OXENO GMBH & CO KG

AI summary

The present invention relates to a mixture of diisononyl esters of 1,2-cyclohexanedicarboxylic acid, wherein the isononyl radicals of the diisononyl esters present in the mixture have a degree of branching of from 1.2 to 2.0, to a process for its preparation and to the use of such mixtures.