Fluorine Atom-Containing Mercapto Compound for Coating Compatibility

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Solution Overview

Problem

Mercapto compounds have low affinity for fluorine-containing polymers and solvents, leading to bleeding and solubility issues in coating liquids, hindering their industrial applications.

Innovation Solution

A novel mercapto compound with a specific fluorine-containing alkyl group is developed, enhancing its affinity for fluorine-containing polymers and solvents through a micelle-like structure formation, improving surface fluorine atom density and compatibility.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If a mercapto compound is used without a fluorine-containing alkyl group, then the compound can be synthesized easily and has good chemical reactivity, but the compound has low affinity for fluorine-containing polymers and solvents, causing bleeding and solubility issues

Engineering Contradiction:
Improveaffinity for fluorine-containing polymerVSAvoidmolecular structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent modifies the molecular structure by introducing a fluorine-containing alkyl group with specific parameters (fluorine substitution ratio of 5-50 atom%, specific fluorine-containing alkyl groups such as -CF3, -C2F5, -C3F7, -C4F9, -C5F11, -C6F13, -C7F15, -C8F17, -C9F19, -C10F21, -C12F25, or -C14F29) to change the chemical properties and improve affinity for fluorine-containing polymers and solvents

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite molecular structure combining the mercapto group (SH) with a fluorine-containing alkyl group, forming a compound that integrates the reactivity of the mercapto group with the compatibility of the fluorine-containing alkyl group for fluorine-based materials

Inventive Principle:
Principle #40Composite materials

2Reliability

If a mercapto compound is used in coating liquids, then the compound can provide chemical functionality, but the compound has low solubility and bleeds out from the materials

Engineering Contradiction:
Improvecompatibility with fluorine-containing solventVSAvoidbleeding from coating
Core Design Contradiction:
ReliabilityVSLoss of substance

Solution Approach 1:

The patent changes the solubility parameters by introducing fluorine atoms into the alkyl group, which modifies the compound's interaction with fluorine-containing solvents, thereby improving solubility and preventing bleeding from coating liquids

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If a mercapto compound without fluorine-containing alkyl group is used, then the synthesis process is simple, but the compound has poor solubility and cannot achieve desired functionality in fluorine-based systems

Engineering Contradiction:
Improvesynthesis simplicityVSAvoidcompatibility with fluorine-containing polymer
Core Design Contradiction:
Ease of manufactureVSAdaptability or versatility

Solution Approach 1:

The patent introduces fluorine-containing alkyl groups with specific parameters to enhance adaptability to fluorine-based systems while maintaining synthesis feasibility through established chemical methods

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 compound exhibits excellent compatibility and affinity for fluorine-containing polymers and solvents, making it suitable for applications such as chain transfer agents, rubber vulcanization, and photographic additives without bleeding or remaining undissolved.

Implementation Method 1

Compounds represented by formula (1) to be described later include a specific fluorine-containing alkyl group in the molecule, and hence are particularly useful as chain transfer agents in radical polymerization reactions

Methodology Applied
Scientific EffectMicelle-like structure formation: Self-Assembly

Implementation Method 2

the affinity for fluorine-containing polymers and fluorine-containing solvents is improved because the surface fluorine atom density is more increased by the branched structure of the terminal of the fluorinated alkyl group

Methodology Applied
Scientific EffectSurface fluorine atom density increase: Adsorption

Data Source

PatentEP2933249B1Fluorine atom-containing mercapto compound
Publication Date: 2016.04.27 FUJIFILM CORP
  • EP2933249B1 patent drawing
  • EP2933249B1 patent drawing
  • EP2933249B1 patent drawing

AI summary

The purpose of the present invention is to provide a novel mercapto compound which has superior affinity to fluorine-containing polymers and fluorine-containing solvents. This compound is represented by formula (1) (in formula (1), R1 and R2 each independently represent a hydrogen atom or an alkyl group; R3 and R4 each independently represent a hydrogen atom or a substituent; n represents 1 or 2; m represents an integer from 1-6; 1 represents an integer from 1-6; q represents 0 or 1; p represents 2 or 3; and p+q represents 3; and X represents a perfluoroalkyl group having 1-14 carbon atoms).