Cyclic Olefin Copolymer Solubility Heat Resistance

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Solution Overview

Problem

Existing cyclic olefin-based copolymers with crosslinkable groups face challenges in solubility in solvents, particularly at high solid content, which affects their impregnability into fiber base materials during circuit board manufacturing.

Innovation Solution

A method for producing a cyclic olefin-based copolymer that balances heat resistance and solubility in solvents by copolymerizing olefins, cyclic non-conjugated dienes, and cyclic olefins in the presence of a catalyst containing a transition metal compound and an organic metal compound, optimizing the content and structure of repeating units to achieve improved solubility and heat resistance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If the content of cyclic olefin-based copolymer is increased to achieve higher heat resistance, then heat resistance is improved, but solubility in solvent deteriorates

Engineering Contradiction:
Improveheat resistanceVSAvoidsolubility in solvent
Core Design Contradiction:
TemperatureVSQuantity of substance

Solution Approach 1:

The patent applies parameter changes by carefully controlling the glass transition temperature (Tg) within 100-250°C and the content of structural units (A), (B), and (C) within specific ranges. This optimization of physical and chemical parameters enables the copolymer to achieve both high heat resistance and improved solubility in solvents like toluene, resolving the contradiction between these two properties.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite copolymer structure by combining three different structural units: (A) olefin units, (B) cyclic non-conjugated diene units with crosslinkable groups, and (C) cyclic olefin units. This composite approach allows the material to exhibit both high heat resistance and good solubility, as each component contributes different properties that complement each other.

Inventive Principle:
Principle #40Composite materials

2Quantity of substance

If the solubility in solvent is improved, then impregnability into fiber base material is improved, but heat resistance may be compromised

Engineering Contradiction:
Improvesolubility in solventVSAvoidheat resistance
Core Design Contradiction:
Quantity of substanceVSTemperature

Solution Approach 1:

The patent optimizes the glass transition temperature parameter to be within 100-250°C, which is the key parameter that simultaneously controls both solubility and heat resistance. By adjusting this parameter along with the compositional ratios of structural units, the copolymer achieves good solubility for impregnation while maintaining high heat resistance.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces local quality by incorporating specific structural units with different functions: unit (B) provides crosslinkable groups for heat resistance, while units (A) and (C) contribute to solubility and processability. This local differentiation of functional groups within the copolymer chain enables simultaneous achievement of both properties.

Inventive Principle:
Principle #3Local quality

3Temperature

If crosslinkable groups are introduced to improve heat resistance, then heat resistance is improved, but solubility in solvent at high solid content deteriorates

Engineering Contradiction:
Improveheat resistanceVSAvoidsolubility at high solid content
Core Design Contradiction:
TemperatureVSQuantity of substance

Solution Approach 1:

The patent controls the content of structural unit (B) containing crosslinkable groups within 1-40% by mole, and optimizes the glass transition temperature to 100-250°C. This parameter optimization ensures that sufficient crosslinkable groups are present for heat resistance while maintaining solubility at high solid content through appropriate molecular weight and compositional balance.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent uses local quality by incorporating crosslinkable groups only in structural unit (B) at controlled concentrations, rather than throughout the entire polymer chain. This localized approach allows the material to exhibit heat resistance through crosslinking while maintaining overall solubility for processing at high solid contents.

Inventive Principle:
Principle #3Local quality

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 improved method results in a cyclic olefin-based copolymer with enhanced solubility in solvents at high solid content, leading to better impregnability into fiber base materials and improved properties in circuit boards, such as stability of dielectric characteristics and mechanical strength.

Implementation Method 1

a method for producing a cyclic olefin-based copolymer in which the cyclic olefin-based copolymer includes (A) one or more repeating units derived from an olefin, (B) one or more repeating units derived from a cyclic non-conjugated diene, and (C) one or more repeating units derived from a cyclic olefin

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP4545576A1Method for producing cyclic olefin copolymer, cyclic olefin copolymer, crosslinked product, film, or sheet, laminate, circuit board, electronic device, and prepreg
Publication Date: 2025.04.30 MITSUI CHEMICALS INC
  • EP4545576A1 patent drawing
  • EP4545576A1 patent drawing
  • EP4545576A1 patent drawing

AI summary

A method for producing a cyclic olefin-based copolymer, in which the cyclic olefin-based copolymer includes (A) one or more repeating units derived from an olefin, (B) one or more repeating units derived from a cyclic non-conjugated diene, and (C) one or more repeating units derived from a cyclic olefin, a glass transition temperature of the cyclic olefin-based copolymer measured by a differential scanning calorimeter (DSC) is equal to or higher than 100°C, the method includes a polymerization step of copolymerizing an olefin, a cyclic non-conjugated diene, and a cyclic olefin in a presence of a catalyst for olefin polymerization, containing a transition metal compound (A) and a compound (B), the transition metal compound (A) contains one or two or more selected from the group consisting of a transition metal compound (A-1) and a transition metal compound (A-2), and the compound (B) contains one or two or more selected from the group consisting of an organic metal compound (B-1), an organic aluminum oxy compound (B-2), and a compound (B-3) that reacts with the transition metal compound (A) to form an ion pair.