Trihexenyl Isocyanurate Crosslinking Agents for High-Temperature Polymers

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Solution Overview

Problem

Current crosslinking agents for high-temperature applications, such as triallyl isocyanurate (TAC) and triallyl isocyanurate (TAICROS), face challenges with high vapor pressure leading to emission problems and uneven crosslinker distribution, and existing bifunctional crosslinkers are less efficient and chemically unstable.

Innovation Solution

The use of trihexenyl isocyanurate as a crosslinking agent, which has lower vapor pressure and improved compatibility with high-melting polymers, allowing for efficient crosslinking and thermal stability, particularly suitable for thermoplastic polymers and elastomers.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If triallyl isocyanurate (TAICROS) is used as a crosslinking agent for high-temperature processing, then thermal stability is improved, but vapor pressure increases leading to loss of crosslinker and emission problems

Engineering Contradiction:
Improveprocessing temperatureVSAvoidvapor pressure
Core Design Contradiction:
TemperatureVSObject-generated harmful factors

Solution Approach 1:

The patent changes the molecular structure parameters of the crosslinking agent by introducing longer alkyl side chains (hexenyl instead of allyl), which fundamentally alters the vapor pressure and thermal behavior. This structural parameter change enables the crosslinker to remain stable at processing temperatures up to 250°C without excessive vapor pressure or emission.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite crosslinking system where trihexenyl isocyanurate serves as the primary crosslinking agent, potentially combined with other stabilizing components. This composite approach allows the material to achieve both high thermal stability and low vapor pressure simultaneously, resolving the contradiction between processing temperature capability and harmful emissions.

Inventive Principle:
Principle #40Composite materials

2Productivity

If triallyl cyanurate (TAC) is used for crosslinking, then crosslinking efficiency is improved, but thermal stability deteriorates due to premature polymerization at high temperatures

Engineering Contradiction:
Improvecrosslinking efficiencyVSAvoidthermal stability
Core Design Contradiction:
ProductivityVSTemperature

Solution Approach 1:

The patent modifies the thermal and chemical parameters of the crosslinking agent by changing the side chain structure from allyl to hexenyl. This parameter change raises the thermal decomposition temperature and prevents premature polymerization, allowing the crosslinker to remain stable and effective during high-temperature processing while maintaining crosslinking efficiency.

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If bifunctional crosslinkers are used, then ease of manufacture is improved, but crosslinking efficiency deteriorates

Engineering Contradiction:
ImprovecompatibilityVSAvoidcrosslinking efficiency
Core Design Contradiction:
Ease of manufactureVSProductivity

Solution Approach 1:

The patent changes the functionality parameter of the crosslinking agent from bifunctional to trifunctional (or higher) by introducing multiple reactive sites in the hexenyl isocyanurate structure. This parameter change enhances crosslinking efficiency while the long alkyl side chains maintain compatibility with fluororubber and other polymers, resolving the contradiction between ease of manufacture and crosslinking performance.

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

Trihexenyl isocyanurate enables crosslinked polymers to withstand higher processing temperatures without premature polymerization, maintaining thermal stability and reducing weight loss, thus addressing the limitations of existing crosslinkers in high-temperature applications.

Implementation Method 1

The invention relates to a process for producing crosslinked organic polymers by reacting a polymer with the crosslinking agent trihexenyl isocyanurate

Methodology Applied
Scientific EffectCrosslinking: Chemical Bonding

Implementation Method 2

it has a significantly lower vapor pressure than TAICROS but comparable crosslinking efficiency and polymerization properties... enabling crosslinking at processing temperatures up to 250°C

Methodology Applied
Scientific EffectThermal stability:

Implementation Method 3

it has the disadvantage that it has a relatively high vapor pressure at these processing temperatures, which leads to a loss of crosslinker and, above all, to emission problems

Methodology Applied
Scientific EffectVapor pressure reduction: Vapour Pressure

Data Source

PatentEP2380928B1Trisalkenyl(ISO)cyanurate cross linking agents and process for producing crosslinked organic polymers
Publication Date: 2018.05.30 EVONIK OPERATIONS GMBH
  • EP2380928B1 patent drawing
  • EP2380928B1 patent drawing

AI summary

Preparing crosslinked organic polymer comprises reacting a polymer with a crosslinking agent comprising 1,3,5-trialkyl triazine trione derivative (I) or 2,4,6-trisalkoxy triazine derivative (II). Preparing crosslinked organic polymer comprises reacting a polymer with a crosslinking agent comprising 1,3,5-trialkyl-triazine trione derivative of formula (I) or 2,4,6-trisalkoxy triazine derivative of formula (II). R 1>-R 3> : divalent spacer carbon group comprising 1-20C alkylene, preferably 1-6C alkylene, 2-20C alkenylene, preferably 2-8C alkenylene (all optionally branched), 6-14C aromatic hydrocarbon (mono- or bicyclic and optionally substituted by 1-4 alkyl or 1-3C alkenyl), 6-14C bivalent cycloaliphatic (all optionally comprise N, S or O), 5-12C cycloalkyl, 5-12C cycloalkenyl or 5-12C cycloalkyldienyl (mono- or bicyclic and optionally substituted by 1-3 alkyl or 1-3C alkenyl). Independent claims are also included for: (1) (I) and (II) excluding trialkylphenyl cyanurate, tris(2-methyl-2-propenyl)cyanurate and tributenylisocyanurate; and (2) a crosslinkable composition comprising a polymer consisting of polyvinyl polymers, polyolefins, polystyrenes, polyacrylates, polymethacrylates, polyesters, polyamides, polycarbonates, polyphenylene ethers, polyphenylene sulfides, polyacetals, polyphenylene sulfones and/or fluoropolymers and (I) or (II). [Image].