Method for producing surface-modified substrate, method for producing conjugate, novel hydrosilane compound, surface treatment agent, surface treatment agent kit, and surface-modified substrate

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Solution Overview

Problem

Conventional methods for surface modification of base materials using halosilanes and alkoxysilanes face limitations, such as high reactivity issues, difficulty in separating and purifying, and the need for high-temperature, long-time treatments, which restrict industrial applicability and uniform modification, especially for porous bodies and internal surfaces.

Innovation Solution

A method involving a dehydrocondensation reaction between a base material with polar groups and a hydrosilane compound containing Si-H groups in the presence of a borane catalyst, allowing for surface modification at lower temperatures and shorter times, using new hydrosilane compounds like 1-(dimethylsilyl)pyrene and (3-dimethylsilyl)propyl)naphthalene, which are easy to separate and purify, and do not undergo hydrolysis.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Speed

If halosilanes are used for surface modification, then high reactivity and suitability for vapor-phase reactions are achieved, but they are unsuitable for liquid-phase reactions and cannot modify internal surfaces of porous bodies

Engineering Contradiction:
Improvereaction rateVSAvoidapplicability to liquid-phase reactions and porous bodies
Core Design Contradiction:
SpeedVSAdaptability or versatility

Solution Approach 1:

The patent changes the chemical parameters of the silicon compound from halosilane to hydrosilane, which fundamentally alters the reaction mechanism. Hydrosilanes react via dehydrocondensation rather than hydrolysis, enabling liquid-phase reactions and penetration into porous structures while maintaining controlled reactivity through catalyst selection.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces a borane catalyst as an intermediary to mediate the reaction between hydrosilane and the base material. This catalyst enables the dehydrocondensation reaction to proceed under mild conditions, facilitating liquid-phase reactions and internal surface modification without requiring the high reactivity of halosilanes.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Adaptability or versatility

If alkoxysilanes are used for surface modification, then liquid-phase reactions are enabled, but they undergo hydrolysis to cause sol-gel reaction progression making separation and purification difficult

Engineering Contradiction:
Improveapplicability to liquid-phase reactionsVSAvoiddifficulty in separation and purification
Core Design Contradiction:
Adaptability or versatilityVSEase of manufacture

Solution Approach 1:

The patent changes the functional group of the silicon compound from alkoxy to hydrido (Si-H). This parameter change eliminates the hydrolysis pathway that causes sol-gel reactions in alkoxysilanes, while still allowing liquid-phase reactions to proceed via dehydrocondensation mechanism with borane catalyst.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent extracts the problematic alkoxy group that causes hydrolysis and sol-gel reactions, replacing it with a hydrido group. This removal eliminates the unwanted side reactions and simplifies separation and purification processes while maintaining the desired liquid-phase reactivity.

Inventive Principle:
Principle #2Taking out (Extraction)

3Adaptability or versatility

If alkoxysilanes are used for surface modification, then liquid-phase reactions are enabled, but high-temperature, long-time treatment is required and uniform modification is difficult due to multimolecular layer formation

Engineering Contradiction:
Improveapplicability to liquid-phase reactionsVSAvoiduniformity of modification
Core Design Contradiction:
Adaptability or versatilityVSManufacturing precision

Solution Approach 1:

The borane catalyst acts as an intermediary that controls the reaction rate and mechanism, enabling uniform monomolecular layer formation at lower temperatures and shorter times. The catalyst mediates the dehydrocondensation reaction to proceed progressively and uniformly across the surface, preventing multimolecular layer formation.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent changes the reaction mechanism from hydrolysis-based (alkoxysilane) to dehydrocondensation-based (hydrosilane with borane catalyst). This parameter change allows the reaction to proceed under milder conditions with better control, achieving uniform modification without high-temperature, long-time treatment.

Inventive Principle:
Principle #35Parameter changes

4Reliability

If conventional methods are used for surface modification, then base materials can be modified, but the process requires high-temperature, long-time treatment reducing productivity

Engineering Contradiction:
Improveeffectiveness of surface modificationVSAvoidproduction efficiency
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The borane catalyst serves as an intermediary that dramatically accelerates the surface modification reaction. By mediating the dehydrocondensation reaction between hydrosilane and base material, the catalyst enables the process to proceed at lower temperatures and shorter times, thereby increasing productivity while maintaining modification effectiveness.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent changes the reaction conditions by introducing borane catalyst and using hydrosilane, which shifts the reaction to proceed under milder conditions (lower temperature, shorter time). This parameter change maintains the reliability of surface modification while significantly improving production efficiency.

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

Enables surface modification of base materials at lower temperatures and shorter times, allowing for a wide variety of options in form, type, and application, and prevents the formation of multimolecular layers, ensuring uniform modification and industrial feasibility.

Implementation Method 1

a dehydrocondensation reaction between a base material with polar groups and a hydrosilane compound containing Si-H groups in the presence of a borane catalyst

Methodology Applied
Scientific EffectDehydrocondensation reaction: Chemical Bonding

Implementation Method 2

in the presence of a borane catalyst so as to allow a dehydrocondensation reaction to take place

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP3118277B1Method for producing surface-modified substrate, method for producing conjugate, novel hydrosilane compound, surface treatment agent, surface treatment agent kit, and surface-modified substrate
Publication Date: 2019.10.23 KYOTO UNIV
  • EP3118277B1 patent drawingFigure 1
  • EP3118277B1 patent drawingFigure 2
  • EP3118277B1 patent drawingFigure 3~4

AI summary

The method for producing a surface-modified base material according to the present invention includes a step of bringing a base material having a polar group present on a surface thereof into contact with a hydrosilane compound having a molecular structure A and having a Si-H group composed of a silicon atom of the molecular structure A and a hydrogen atom bonded to the silicon atom in the presence of a borane catalyst so as to allow a dehydrocondensation reaction to take place between the base material and the compound, thereby forming the base material surface-modified with the molecular structure A. This production method is capable of surface-modifying a base material at a lower temperature in a shorter time than conventional methods and allows a wide variety of options for the form, type, and application of the base material, the mode of the modification reaction, and the type of the molecular structure with which the base material is surface-modified.