Degradable Cross-Linking Agent With High Solvent Solubility

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Solution Overview

Problem

Diacylhydrazine compounds used in polymers have poor solvent solubility, limiting their formulation options and posing environmental burdens in applications like paints, which involve solvent drying and removal.

Innovation Solution

A hydrazine derivative with a specific structure is developed, enhancing solvent solubility and allowing for improved formulation with resins and polymerization initiators.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If degradable polymers with diacylhydrazine structure are used, then degradability is improved, but solvent solubility deteriorates

Engineering Contradiction:
ImprovedegradabilityVSAvoidsolvent solubility
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The molecule is divided into distinct functional segments: a degradable diacylhydrazine core segment and solubility-enhancing side chain segments containing polar groups. This segmentation allows each segment to independently fulfill its function - the core provides degradability while the side chains provide solvent compatibility

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

Different parts of the molecule are assigned different properties: the central diacylhydrazine portion maintains degradable character while the peripheral side chains are designed with polar groups (carboxyl, hydroxyl, amino, ether, or ester groups) to provide local solubility enhancement in specific solvent environments

Inventive Principle:
Principle #3Local quality

2Adaptability or versatility

If high-boiling-point aprotic polar solvents or strong acids are used to achieve solubility, then solvent solubility is improved, but environmental burden increases

Engineering Contradiction:
Improvesolvent solubilityVSAvoidenvironmental burden
Core Design Contradiction:
Adaptability or versatilityVSObject-generated harmful factors

Solution Approach 1:

The chemical structure parameters of the crosslinking agent are modified by introducing side chains with specific polar functional groups. This changes the solubility parameters of the molecule, enabling it to dissolve in environmentally friendly solvents with lower boiling points rather than requiring high-boiling-point aprotic polar solvents or strong acids

Inventive Principle:
Principle #35Parameter changes

3Reliability

If diacylhydrazine compounds are used as crosslinking agents, then degradable cross-linking capability is improved, but formulation flexibility deteriorates due to poor solubility

Engineering Contradiction:
Improvedegradable cross-linking capabilityVSAvoidformulation flexibility
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The crosslinking agent is designed as a composite molecular structure combining the degradable diacylhydrazine functional core with side chains containing various polar groups. This composite structure integrates multiple functionalities: crosslinking capability from the core, degradability from the diacylhydrazine linkage, and formulation flexibility from the solubility-providing side chains

Inventive Principle:
Principle #40Composite materials

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 degradable cross-linking agent exhibits high solvent solubility, facilitating flexible cross-linking and reducing environmental impact.

Implementation Method 1

The degradable cross-linking agent of the present invention has excellent solvent solubility

Methodology Applied
Scientific EffectSolvation: Solvation

Implementation Method 2

They are stable in the air due to the presence of the diacylhydrazine structure, while they are rapidly degraded when reacted with oxidizing agents such as sodium hypochlorite

Methodology Applied
Scientific EffectOxidation: Oxidation

Data Source

PatentEP4685195A1Degradable crosslinking agent
Publication Date: 2026.01.28 NAGASE CHEMTEX CORPORATION
  • EP4685195A1 patent drawing
  • EP4685195A1 patent drawing
  • EP4685195A1 patent drawing

AI summary

The present invention provides a degradable cross-linking agent that is highly soluble in solvents. The present invention relates to a degradable cross-linking agent including a compound represented by the following formula (1), wherein - n ≥ 0, k ≥ 0, m ≥ 0, p1 ≥ 1, p2 ≥ 1, and p3 ≥ 1; - R1, R2, and R3 each independently represent a single bond or a C1-C500 hydrocarbon optionally containing a substituent or a heteroatom; - Q1, Q2, and Q3 each independently represent at least one reactive functional group selected from the group consisting of a hydroxy group, an amino group, a thiol group, a hydrazide group, a carboxylic acid group, an acid anhydride group, a vinyl group, an allyl group, an acrylate group, a methacrylate group, a crotonate group, an isoprenyl group, an acrylamide group, a methacrylamide group, a crotonamide group, an epoxy group, an oxetane group, an oxazoline group, an isocyanate group, a carbodiimide group, a methylol group, a silanol group, a hydroxysilyl group, and an alkoxysilyl group; - X1a, X1b, X2a, X2b, X3a, X3b, X4a, and X4b each independently represent an oxygen atom, a sulfur atom, a single bond, a C1-C20 hydrocarbon group optionally containing a substituent, or -NB- where B represents a hydrogen atom or a hydrocarbon group, and at least one of X1a, X1b, X2a, X2b, X3a, X3b, X4a, and X4b is an oxygen atom, a sulfur atom, or -NB- where B represents a hydrogen atom or a hydrocarbon group; - A1 to A8 each represent a carbonyl group or a single bond, at least one of A1 and A2 is a carbonyl group, at least one of A3 and A4 is a carbonyl group, at least one of A5 and A6 is a carbonyl group, and at least one of A7 and A8 is a carbonyl group; and - each Z independently represents a divalent or higher-valent group containing a siloxane structure or a C l-C500 hydrocarbon group optionally containing a heteroatom.