Vinyl-Containing Compounds Reducing Styrene Emissions

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Solution Overview

Problem

Current methods for reducing styrene emissions in open mold processes using thermosetting resins face challenges such as slower reactivity, incomplete curing, higher costs, and compromised physical properties, while also generating hazardous byproducts and requiring additional processing steps.

Innovation Solution

A process involving reacting a dicarboxylic acid or anhydride with a polyhydric alcohol under a nitrogen atmosphere, followed by reacting the hydroxyl-containing polyester with a vinyl-containing organic acid in the presence of an esterification catalyst and azeotropic agent, and then with an epoxy to form vinyl-containing compounds, which reduces the need for multiple processing steps and minimizes hazardous air pollutants.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Object-affected harmful factors

If styrene is replaced by another reactive diluent, then styrene emissions are reduced, but reactivity becomes slower and curing becomes incomplete

Engineering Contradiction:
Improvestyrene emissionsVSAvoidcuring completeness
Core Design Contradiction:
Object-affected harmful factorsVSReliability

Solution Approach 1:

The patent changes the chemical structure parameters by using vinyl-containing organic acids with specific molecular weights and structures. This allows maintaining high reactivity and complete curing while reducing styrene emissions, as the vinyl groups provide sufficient reactivity without requiring high styrene content

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite system combining hydroxyl-containing polyester with vinyl-containing organic acid and epoxy. This composite approach enables complete curing and high reactivity through the synergistic reaction of multiple components, eliminating the need for high styrene content while ensuring reliable curing

Inventive Principle:
Principle #40Composite materials

2Object-affected harmful factors

If the amount of styrene or reactive diluent is reduced, then emissions are minimized, but viscosity increases making handling difficult

Engineering Contradiction:
ImproveemissionsVSAvoidhandling ease
Core Design Contradiction:
Object-affected harmful factorsVSEase of operation

Solution Approach 1:

The patent optimizes the molecular weight and structure parameters of the vinyl-containing organic acid to achieve the right balance between reactivity and viscosity. By selecting appropriate molecular weights, the system maintains low viscosity for easy handling while using minimal styrene content to reduce emissions

Inventive Principle:
Principle #35Parameter changes

3Ease of operation

If low molecular weight polymers are used, then viscosity decreases improving handling, but physical properties of final products are compromised

Engineering Contradiction:
Improvehandling easeVSAvoidphysical properties
Core Design Contradiction:
Ease of operationVSStrength

Solution Approach 1:

The patent carefully controls the molecular weight parameter of the hydroxyl-containing polyester and the degree of vinyl group incorporation. This allows achieving optimal balance where the polymer has sufficient chain length for good physical properties while maintaining low enough viscosity for easy handling through the vinyl-containing organic acid modification

Inventive Principle:
Principle #35Parameter changes

4Object-affected harmful factors

If waxes are added to limit diluent vapor elimination, then emissions are controlled, but interlaminate bonding becomes poor

Engineering Contradiction:
ImproveemissionsVSAvoidinterlaminate bonding
Core Design Contradiction:
Object-affected harmful factorsVSStrength

Solution Approach 1:

The patent extracts and eliminates the need for wax additives by using a fundamentally different chemical approach. The vinyl-containing organic acid reacts with the hydroxyl-containing polyester and epoxy to form a crosslinked network that controls emissions through chemical reaction rather than physical barrier, thereby maintaining good interlaminate bonding

Inventive Principle:
Principle #2Taking out (Extraction)

5Productivity

If high reaction temperatures are used in esterification, then ester yield improves, but color becomes dark requiring washing

Engineering Contradiction:
Improveester yieldVSAvoidcolor
Core Design Contradiction:
ProductivityVSIllumination intensity

Solution Approach 1:

The patent changes the reaction temperature parameter and catalyst selection to operate at lower temperatures while maintaining high ester yield. By optimizing these parameters, the reaction proceeds efficiently without generating the dark color byproducts that form at high temperatures, eliminating the need for washing steps

Inventive Principle:
Principle #35Parameter changes

6Manufacturing precision

If multiple processing steps are used in prior art processes, then purification is achieved, but time and complexity increase

Engineering Contradiction:
ImprovepurificationVSAvoidprocessing time
Core Design Contradiction:
Manufacturing precisionVSLoss of time

Solution Approach 1:

The patent merges multiple processing steps into a single integrated reaction process. The esterification, crosslinking, and purification occur in one operation, eliminating the need for separate extraction, washing, and filtration steps. This unified approach achieves the required purification while significantly reducing processing time and complexity

Inventive Principle:
Principle #5Merging (Combining)

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

This approach results in vinyl-containing compounds with low color, high reactivity, and reduced styrene content, enabling room temperature crosslinking without the need for extraction or washing, and maintains excellent mechanical properties.

Implementation Method 1

reacting the hydroxyl-containing polyester with a vinyl-containing organic acid in the presence of an esterification catalyst

Methodology Applied
Scientific EffectEsterification: Chemical Bonding

Implementation Method 2

reacting the hydroxyl-containing polyester with a vinyl-containing organic acid in the presence of an esterification catalyst and an azeotropic agent

Methodology Applied
Scientific EffectAzeotropic distillation: Distillation

Implementation Method 3

reacting the vinyl functional esterified intermediate, residual esterification catalyst and residual vinyl-containing organic acid with an epoxy to provide the vinyl-containing compound

Methodology Applied
Scientific EffectRing opening: Chemical Bonding

Data Source

PatentUS10570107B2Vinyl-containing compounds and processes for making the same
Publication Date: 2020.02.25 POLYNT COMPOSITES USA INC
  • US10570107B2 patent drawing
  • US10570107B2 patent drawing
  • US10570107B2 patent drawing

AI summary

The present invention provides a process for forming vinyl-containing compounds including the steps of: a) reacting in a nitrogen atmosphere a dicarboxylic acid and/or anhydride and a functional mono or polyfunctional alcohol to provide a hydroxyl-containing polyester; b) reacting the hydroxyl-containing polyester with a vinyl-containing organic acid in the presence of an esterification catalyst, a polymerization inhibitor and an azeotropic agent; and c) reacting the vinyl functional esterified intermediate, residual esterification catalyst and residual vinyl-containing organic acid with an epoxy to provide the vinyl-containing compound.