Polyfluoroalkylphosphonic Acid Ester Mold Release Agent

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Solution Overview

Problem

Current mold-releasing agents with perfluoroalkyl groups containing 6 or less carbon atoms have low bioaccumulation potential but fail to provide mold release performance equivalent to those with 8 or more carbon atoms, and their production generates environmental concerns and durability issues.

Innovation Solution

A polyfluoroalkylphosphonic acid oxyalkylene ester with a perfluoroalkyl group containing 6 or less carbon atoms is developed, which undergoes HF-elimination and ozone decomposition, reducing environmental impact and bioaccumulation, and is used as an active ingredient in mold-releasing agents, enhancing mold release performance and durability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If phosphate or phosphonate compounds having a C8-C12 perfluoroalkyl group are used as mold-releasing agents, then mold release performance and durability are improved, but environmental bioaccumulation risk increases and harmful substances are generated during production

Engineering Contradiction:
Improvemold release performanceVSAvoidenvironmental bioaccumulation risk
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The invention changes the carbon atom number parameter of the perfluoroalkyl group from 8-12 to 6 or less, which fundamentally alters the environmental behavior of the compound. This parameter change reduces the compound's bioaccumulation potential and environmental persistence while maintaining adequate mold release performance through optimized molecular structure and oxyalkylene group integration

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention converts the previously harmful long-chain perfluoroalkyl groups (C8-C12) into beneficial short-chain perfluoroalkyl groups (C6 or less) that exhibit lower environmental toxicity and bioaccumulation potential. The harmful environmental persistence is transformed into beneficial environmental degradability while maintaining functional performance

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

2Duration of action of stationary object

If phosphate or phosphonate compounds having a C8-C12 perfluoroalkyl group are used, then mold release durability is improved, but perfluorooctanoic acid with high bioaccumulation potential is generated during production

Engineering Contradiction:
Improvemold release lifeVSAvoidperfluorooctanoic acid generation
Core Design Contradiction:
Duration of action of stationary objectVSObject-generated harmful factors

Solution Approach 1:

The invention converts the harmful byproduct generation (perfluorooctanoic acid from C8-C12 compounds) into a beneficial outcome by using C6 or less perfluoroalkyl groups that do not generate persistent harmful substances during production. The production process becomes environmentally benign while maintaining durable mold release performance

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

Solution Approach 2:

The invention changes the carbon chain length parameter to prevent the formation of harmful byproducts during synthesis. By limiting the perfluoroalkyl group to 6 or less carbon atoms, the production process avoids generating perfluorooctanoic acid and similar harmful substances while achieving the desired mold release durability

Inventive Principle:
Principle #35Parameter changes

3Object-affected harmful factors

If compounds having a perfluoroalkyl group containing 6 or less carbon atoms are used, then environmental safety is improved, but mold release performance and durability are insufficient

Engineering Contradiction:
Improveenvironmental safetyVSAvoidmold release performance
Core Design Contradiction:
Object-affected harmful factorsVSReliability

Solution Approach 1:

The invention creates a composite molecular structure combining a short-chain perfluoroalkyl group (C6 or less) with an oxyalkylene group and phosphonate/phosphate functionality. This composite structure integrates the environmental safety of short-chain compounds with the performance characteristics needed for effective mold release, achieving both ecological and functional requirements

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The invention applies local quality by concentrating the functional performance in the oxyalkylene and phosphonate regions of the molecule while keeping the perfluoroalkyl tail short for environmental safety. Different parts of the molecule serve different functions: the perfluoroalkyl group provides environmental compatibility, while the oxyalkylene-phosphonate portion delivers mold release performance

Inventive Principle:
Principle #3Local quality

4Ease of operation

If silicone oil or wax are used as mold-releasing agents, then mold releasability is excellent, but coating uniformity and secondary processability are impaired due to transfer to molded products

Engineering Contradiction:
Improvemold releasabilityVSAvoidcoating uniformity
Core Design Contradiction:
Ease of operationVSManufacturing precision

Solution Approach 1:

The invention uses a fluorinated phosphonate compound that forms a stable film on the mold surface but does not transfer to the molded product. This disposable-like behavior on the mold surface (remaining on mold, not transferring) ensures consistent release performance without contaminating the product, unlike silicone oil and wax which transfer and cause defects

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

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 polyfluoroalkylphosphonic acid oxyalkylene ester exhibits excellent mold releasability, film-forming properties, and durability, reducing mold contamination and improving dimensional accuracy of molded products, while avoiding the production of harmful environmental substances.

Implementation Method 1

the polyfluoroalkylphosphonic acid oxyalkylene ester of the present invention undergoes HF-elimination in the -CH 2 CF 2 -bonding site of the molecule

Methodology Applied
Scientific EffectHF-elimination:

Implementation Method 2

The result is then subjected to ozone decomposition etc. to have a structure that is easily decomposed into a compound with low environmental concentration and low bioaccumulation potential

Methodology Applied
Scientific EffectOzone decomposition: Ozone

Data Source

PatentEP2476687B1Polyfluoroalkylphosphonic acid oxyalkylene ester, method for producing same and release agent containing same as active ingredient
Publication Date: 2013.12.25 UNIMATEC CO LTD

AI summary

Disclosed is a polyfluoroalkylphosphonic acid oxyalkylene ester of the formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cP(O)[O(RO)mR']d(OH)2-d (RO is a C2-C6 linear or branched oxyalkylene group, R' is a hydrogen atom or a C1-C20 alkyl group or aralkyl group, n is 1 to 6, a is 1 to 4, b is 1 to 3, c is 1 to 3, d is 1 or 2, and m is 1 to 100), which is a compound having a perfluoroalkyl group containing 6 or less carbon atoms and referred to as having low bioaccumulation potential, and exhibiting, when used as an active ingredient of a mold-releasing agent, mold release performance equivalent to that of a compound having a perfluoroalkyl group containing 8 or more carbon atoms. This compound is produced by subjecting a polyfluoroalkylphosphonic acid of the formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cP(O)(OH)2 and a polyalkyleneglycol or a monoether thereof of the formula: HO (RO)mR' to a condensation reaction.