Modified Conjugated Diene Polymer Production via Silane-Amine Modification

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Solution Overview

Problem

The existing methods for producing modified conjugated diene-based polymers require multiple steps and result in inferior silica dispersibility, leading to insufficient heat build-up in crosslinked rubber, necessitating a more efficient production method that reduces steps and improves silica interaction.

Innovation Solution

A method involving the reaction of a conjugated diene-based polymer with a compound containing alkoxysilyl groups and specific imino groups to produce a modified polymer with enhanced silica interaction and reduced production steps, achieving high Mooney viscosity and low heat build-up.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If a modified conjugated diene-based polymer is produced by reacting with metal halogen compound as in Patent Document 1, then good shape stability and processability are achieved, but the number of production steps increases

Engineering Contradiction:
Improveshape stabilityVSAvoidnumber of production steps
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The patent combines the modification step and crosslinking step into a single reaction process. The conjugated diene-based polymer is reacted with both the crosslinking agent (containing silane and amine groups) and the metal halogen compound simultaneously, achieving crosslinking and modification in one step rather than sequentially. This reduces the number of production steps while maintaining the desired shape stability and processability.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The patent introduces a preliminary modification step where the conjugated diene-based polymer is pre-modified with a compound containing silane and amine groups before crosslinking. This preliminary action creates active sites on the polymer chains that facilitate subsequent crosslinking with metal halogen compounds, enabling the reaction to proceed more efficiently and reducing the number of additional steps required.

Inventive Principle:
Principle #10Preliminary action

2Adaptability or versatility

If a modified conjugated diene-based polymer is produced by reacting with compound having methyleneamino group and alkoxysilyl group as in Patent Document 2, then good interaction with carbon black and silica is achieved, but dispersibility of silica is inferior

Engineering Contradiction:
Improveinteraction with reinforcing agentsVSAvoidsilica dispersibility
Core Design Contradiction:
Adaptability or versatilityVSManufacturing precision

Solution Approach 1:

The patent modifies the polymer chains with compounds containing both silane groups (for silica interaction) and amine groups (for carbon black interaction) at different locations along the polymer chain. This creates local regions with different affinities for different reinforcing agents, allowing the polymer to interact effectively with both carbon black and silica while maintaining good silica dispersibility. The dual-functional modifier enables selective interaction at different sites on the polymer chain.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent uses a composite modifier structure that combines silane groups and amine groups within the same modifying compound. This composite approach allows a single modifier to provide multiple functions: the silane groups interact with silica particles while the amine groups interact with carbon black, creating a synergistic effect that improves both reinforcement and dispersibility simultaneously.

Inventive Principle:
Principle #40Composite materials

3Reliability

If existing production methods are used, then modified polymer can be obtained, but heat build-up in crosslinked rubber is insufficient

Engineering Contradiction:
ImprovedurabilityVSAvoidheat build-up
Core Design Contradiction:
ReliabilityVSTemperature

Solution Approach 1:

The patent changes the chemical structure parameters of the modifier to achieve lower heat build-up. Specifically, it uses modifiers with controlled silane group content and specific amine group structures that result in crosslinked networks with optimized free volume and chain mobility. These parameter changes lead to reduced hysteresis loss and lower heat build-up in the crosslinked rubber, while maintaining durability through effective crosslinking.

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 method allows for the production of a modified conjugated diene-based polymer with improved silica dispersibility and reduced production steps, resulting in a crosslinked rubber with excellent processability and low heat build-up.

Implementation Method 1

reacting a conjugated diene-based polymer having an active chain end with a compound [M] having at least two groups selected from the group consisting of a group '-C(R1R2)=NR3' wherein R1 to R4 are the same as defined in the claims

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Implementation Method 2

a compound having a methyleneamino group and an alkoxysilyl group such as N-(1,3-dimethylbutylidene)-3-triethoxysilyl-1-propanamine, thereby allowing the polymer to exhibit a good interaction to both of carbon black and silica

Methodology Applied
Scientific EffectAdsorption: Adsorption

Data Source

PatentEP3476866B1Method for producing modified conjugated diene polymer, modified conjugated diene polymer, polymer composition, crosslinked body, tire and compound
Publication Date: 2022.01.05 JSR CORPORATION
  • EP3476866B1 patent drawing
  • EP3476866B1 patent drawing
  • EP3476866B1 patent drawing

AI summary

A modified conjugated diene-based polymer having high Mooney viscosity and good shape stability and exhibiting excellent processability and low heat build-up is obtained in as few steps as possible. The modified conjugated diene-based polymer is produced by a method of reacting a conjugated diene-based polymer having an active chain end, obtained by polymerizing a monomer containing a conjugated diene compound in the presence of an initiator that contains at least either of an alkali metal compound and an alkaline earth metal compound, with a compound [M] having two or more groups in total of at least either of a group "-C(R1)=N-A1" or a group "-N=C(R1)-A1" (where R1 is a hydrogen atom or a hydrocarbyl group and A1 is a monovalent group having an alkoxysilyl group.