OXO-Ester Plasticizers for Non-Phthalate PVC Compatibility
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Solution Overview
Problem
There is a need for alternative non-phthalate plasticizers that offer good melting and chemical stability, compatibility, and low-temperature properties to replace traditional phthalate esters, particularly in applications where phthalates are being phased out due to safety concerns, such as in food-contact materials and medical products.
Innovation Solution
Development of OXO-ester plasticizers made from cyclohexyl benzene derivatives, which involve reacting benzene or alkylated benzene with alcohols to form alkylated biphenyl, oxidizing the alkyl groups to create acid groups, and subsequently esterifying them with OXO-alcohols to produce mono- or diesters, providing a cost-effective and efficient manufacturing process.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If phthalate esters are used as plasticizers, then good plasticizing performance is achieved, but safety concerns arise due to health and environmental issues
Solution Approach 1:
The invention changes the chemical structure parameters of the plasticizer by using non-phthalate esters (such as adipate, azelate, sebacate, and other dicarboxylic acid esters) instead of phthalate esters. This structural parameter change maintains the desired plasticizing performance while eliminating the harmful effects associated with phthalates, particularly in food-contact and medical applications.
2Object-affected harmful factors
If alternative non-phthalate plasticizers are developed, then safety concerns are addressed, but compatibility and performance may be compromised
Solution Approach 1:
The invention optimizes the molecular parameters of non-phthalate plasticizers by selecting specific dicarboxylic acids (adipic, azelic, sebacic acids) with appropriate carbon chain lengths and structures. These parameter optimizations ensure that the alternative plasticizers achieve compatibility and performance levels comparable to traditional phthalates while maintaining safety advantages.
Solution Approach 2:
The invention employs composite approaches by using blends or combinations of different non-phthalate esters (adipate, azelate, sebacate esters) to achieve synergistic effects that enhance overall performance and compatibility while maintaining the safety benefits of non-phthalate formulations.
3Ease of manufacture
If traditional plasticizer manufacturing processes are used, then established production methods are maintained, but manufacturing complexity and cost increase
Solution Approach 1:
The invention segments the plasticizer production into distinct chemical pathways starting from different feedstocks (benzene for phthalates, cyclohexane for adipates/azelates/sebacates). This segmentation allows each pathway to be optimized independently, simplifying the overall manufacturing process by enabling choice of route based on desired product properties and feedstock availability.
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 OXO-ester plasticizers demonstrate improved thermal stability, compatibility, and low-temperature performance, making them suitable replacements for phthalate esters in various polymer systems, including PVC, while maintaining economic viability through reduced manufacturing steps.
Implementation Method 1
reacting benzene or alkylated benzene with alcohols to form alkylated biphenyl
Implementation Method 2
oxidizing the alkyl groups to create acid groups
Implementation Method 3
subsequently esterifying them with OXO-alcohols to produce mono- or diesters
Data Source
AI summary
Provided are compounds of the following:wherein R1 is a saturated or unsaturated cyclic hydrocarbon optionally substituted with an alkyl and/or an OXO-ester, and R2 is a C4 to C14 hydrocarbyl, preferably the residue of a C4 to C14 OXO-alcohol. Also provided are processes for making the compounds and plasticized polymer compositions containing said compounds.