Fluorine Phosphate Ester-Amide Hydrolysis Resistance

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Solution Overview

Problem

Fluorine-containing phosphate esters face challenges with insufficient hydrolysis resistance and flame retardancy, particularly when used as additives in resins, electrolytes, and organic synthesis solvents, due to their susceptibility to hydrolysis and acidity, which affects their durability and performance.

Innovation Solution

A fluorine-containing phosphate ester-amide with a specific structure, featuring branched alkyl groups and secondary or tertiary carbon atoms bonded to nitrogen, exhibits improved hydrolysis resistance and maintains flame retardancy even with small additions, allowing for long-term effectiveness in various applications.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If fluorine-containing phosphate esters are used to improve flame retardancy, then flame retardant effect is enhanced, but hydrolysis resistance deteriorates

Engineering Contradiction:

Improveflame retardancyVSAvoidhydrolysis resistance

Core Design Contradiction:

ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent changes the chemical structure parameters by replacing ester groups with amide groups in the phosphate ester molecule. This structural modification transforms the compound from a phosphate ester to a phosphate ester-amide, fundamentally altering its chemical properties to achieve both flame retardancy and hydrolysis resistance simultaneously

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite functional structure by combining phosphate ester and amide moieties into a single molecule. The phosphate ester portion provides flame retardancy while the amide portion provides hydrolysis resistance, achieving synergistic effects that resolve the technical contradiction

Inventive Principle:

Principle #40Composite materials

2Reliability

If phosphate esters are added in larger amounts to improve flame retardancy, then flame retardant effect increases, but influence on physical properties of the base substance worsens

Engineering Contradiction:

Improveflame retardancyVSAvoidinfluence on physical properties

Core Design Contradiction:

ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent changes the molecular weight parameter and chemical structure of the flame retardant compound. The fluorine-containing phosphate ester-amide has a specific molecular structure that provides high flame retardant efficiency, allowing effective flame protection at lower concentrations and thus minimizing impact on the physical properties of the base material

Inventive Principle:

Principle #35Parameter changes

3Ease of operation

If conventional phosphate esters are used as solvents or electrolytes, then they provide good solubility and conductivity, but their flammability worsens safety

Engineering Contradiction:

Improvesolubility and conductivityVSAvoidflammability

Core Design Contradiction:

Ease of operationVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical composition by incorporating fluorine atoms and amide groups into the phosphate ester structure. This molecular modification raises the flash point and improves thermal stability while maintaining the solubility and conductivity properties needed for electrolyte and solvent applications

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention converts the typically harmful effect of fluorine atoms (which reduce hydrolysis resistance in phosphate esters) into a beneficial feature. By combining fluorine with the amide group, the compound achieves both high flame retardancy and improved hydrolysis resistance, turning a potential disadvantage into an advantage

Inventive Principle:

Principle #22Blessing in disguise (Convert harm into benefit)

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 fluorine-containing phosphate ester-amide demonstrates superior hydrolysis resistance and flame retardancy, maintaining effectiveness across a wide temperature range and compatibility with organic compounds, making it suitable for diverse applications including resins, electrolytes, and organic synthesis solvents.

Implementation Method 1

One particular problem of the phosphate esters is that they easily undergo hydrolysis because of their chemical stability

Methodology Applied

Scientific EffectHydrolysis: Hydrolysis

Data Source

PatentEP2832737B1Fluorine-containing phosphate ester-amide, and flame retardant resin, flame retardant liquid and flame retardant solvent for oranic synthesis containing same

Publication Date: 2018.08.01 TOSOH FINECHEM CORP

AI summary

[Problem] To provide a fluorine-containing phosphate ester-amide which has high flame retardancy such as exhibiting flame retardant effects at a small quantity of addition, and sufficient hydrolysis resistance. [Solution] A fluorine-containing phosphate ester-amide represented by general formula (1). (In the formula, R1 and R2 are the same or different and represent a branched or linear alkyl group having 1 to 20 carbon atoms in which at least one carbon bonded to a nitrogen atom is a secondary or tertiary carbon, wherein R1 and R2 may have a substituent group selected from the group consisting of an alkoxy group, a hydroxy group, an amino group, a methyl amino group, an ethyl amino group, a dimethyl amino group, diethyl amino group and a fluorine atom. In addition, R1 and R2 may be bonded together to form a five- to eight-membered cyclic structure. X and Y are the same or different and represent a hydrogen atom or a fluorine atom, and n and m represent an integer of 1 to 6.)