TOFA-Based Morpholide Plasticizer for Low-Migration PVC

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Solution Overview

Problem

Current PVC plasticizer compositions face challenges with high carbon footprint, poor compatibility, and excessive migration, particularly in high-temperature applications, and lack optimal balance between plasticizing efficiency and low migration tendency, especially in phthalate-free and bio-based alternatives.

Innovation Solution

Development of a morpholide composition derived from tall oil fatty acids (TOFA) with a low carbon footprint, comprising 20-55 wt.% oleic acid and 20-55 wt.% linoleic acid, which forms a stable reaction product with morpholine, used as a plasticizer in PVC compositions, along with optional linolenic acid, to achieve improved compatibility and reduced migration.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If phthalate-based plasticizers (e.g., DEHP) are used, then plasticizing efficiency is improved, but migration rate becomes too high for high-temperature applications

Engineering Contradiction:
Improveplasticizing efficiencyVSAvoidmigration rate
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The invention changes the chemical structure parameters of the plasticizer by using morpholine compounds with specific molecular weight and structural characteristics. This modifies the plasticizer's interaction with PVC, achieving both good plasticizing efficiency and reduced migration by altering the molecular parameters rather than simply selecting from existing plasticizer types.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention uses composite plasticizer compositions comprising multiple components including morpholine derivatives and auxiliary plasticizers. This composite approach allows optimization of both plasticizing efficiency and migration resistance by combining materials with complementary properties, where the morpholine component provides low migration and the auxiliary components enhance overall performance.

Inventive Principle:
Principle #40Composite materials

2Object-generated harmful factors

If non-phthalate plasticizers (e.g., TOTM) are used, then migration rate is reduced for high-temperature applications, but plasticizing efficiency becomes poor

Engineering Contradiction:
Improvemigration rateVSAvoidplasticizing efficiency
Core Design Contradiction:
Object-generated harmful factorsVSReliability

Solution Approach 1:

The invention optimizes the molecular parameters of the plasticizer by selecting morpholine compounds with specific molecular weights (115-200 g/mol) and structural features. This parameter optimization enables the plasticizer to achieve both low migration characteristics and sufficient plasticizing efficiency, overcoming the limitation of conventional non-phthalate plasticizers.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention employs composite plasticizer systems where morpholine derivatives are combined with auxiliary plasticizers in specific ratios. This composite formulation allows the system to achieve good plasticizing efficiency while maintaining the low migration characteristics of the morpholine component, thus overcoming the poor efficiency of single-component non-phthalate plasticizers.

Inventive Principle:
Principle #40Composite materials

3Object-affected harmful factors

If bio-based plasticizers (e.g., sebacates, citrates, epoxidized soybean oil) are used, then carbon footprint is reduced, but PVC compatibility and plasticizing efficiency are insufficient

Engineering Contradiction:
Improvecarbon footprintVSAvoidPVC compatibility
Core Design Contradiction:
Object-affected harmful factorsVSReliability

Solution Approach 1:

The invention changes the chemical structure parameters of bio-based plasticizers by introducing morpholine rings and optimizing carbon chain lengths. This structural modification improves PVC compatibility and plasticizing efficiency while maintaining the low carbon footprint advantage of bio-based feedstocks, thus overcoming the compatibility limitations of conventional bio-plasticizers.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite plasticizer systems combining modified bio-based morpholine derivatives with auxiliary plasticizers. This composite approach enhances PVC compatibility and overall plasticizing efficiency while preserving the environmentally friendly characteristics of the bio-based components, thus resolving the compatibility issue of pure bio-based plasticizers.

Inventive Principle:
Principle #40Composite materials

4Object-generated harmful factors

If cyclic monoamides (e.g., pyrrolidone derivatives) are used, then migration rate is reduced, but plasticizing efficiency and PVC compatibility are poor

Engineering Contradiction:
Improvemigration rateVSAvoidplasticizing efficiency
Core Design Contradiction:
Object-generated harmful factorsVSReliability

Solution Approach 1:

The invention changes the molecular parameters by using morpholine compounds with optimized molecular weights (115-200 g/mol) and specific structural features. This parameter optimization provides both low migration characteristics and sufficient plasticizing efficiency, overcoming the poor efficiency and compatibility issues of cyclic monoamides while maintaining their low migration advantage.

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 TOFA-based morpholide composition provides a low carbon footprint, excellent PVC compatibility, and balanced plasticizing efficiency with minimal migration, suitable for various applications including high-temperature uses, while maintaining favorable properties such as low exudation and color stability.

Implementation Method 1

a reaction product of a morpholine compound and a fatty acid

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Data Source

PatentUS11279813B2PVC plasticizers and methods for making thereof
Publication Date: 2022.03.22 KRATON POLYMERS LLC

AI summary

A plasticized PVC composition free of phthalate and having low color is disclosed. The composition comprises a morpholide plasticizer prepared from a fatty acid selected from a tall oil fatty acid, a tall oil fatty acid monomer derived therefrom, and mixtures thereof. The fatty acid has a total carbon footprint of <95% of the total carbon footprint of a fatty acid obtained from a vegetable oil. The morpholide is prepared from the reaction of a tall oil fatty acid with morpholine in the presence of a catalyst.