Cyclohexanone Oxime Anti-Skinning Composition in Oil-Based Coatings

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Solution Overview

Problem

The use of cyclohexanone oxime as an anti-skinning agent in oil-based coating materials is limited due to its toxicity and difficulty in handling in pure form, leading to regulatory concerns and inefficient shipping and storage, while existing solvents have low flash points and high VOC content, making it challenging to deliver concentrated solutions effectively.

Innovation Solution

A clear, homogeneous solution of cyclohexanone oxime is achieved by dissolving it in suitable fatty acids, such as saturated or unsaturated fatty acids, which maintains stability over a broad temperature range, has a high flash point, and is compatible with oil-based coating materials, allowing for efficient shipping and storage.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If cyclohexanone oxime is used in pure form as anti-skinning agent, then anti-skinning performance is achieved, but handling difficulty and toxicity increase

Engineering Contradiction:
Improveanti-skinning performanceVSAvoidhandling difficulty
Core Design Contradiction:
ReliabilityVSEase of operation

Solution Approach 1:

The patent uses fatty acids as intermediary substances to dissolve cyclohexanone oxime, creating a concentrated solution that is easier to handle than pure cyclohexanone oxime. The fatty acid acts as a mediator between the anti-skinning agent and the coating material, maintaining effectiveness while improving handling properties.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent changes the physical state and concentration parameters by creating a concentrated solution (20-90 mass percent cyclohexanone oxime) in fatty acid solvent. This transforms the pure crystalline solid into a manageable liquid solution with optimized concentration for effective anti-skinning performance.

Inventive Principle:
Principle #35Parameter changes

2Quantity of substance

If concentrated cyclohexanone oxime solution is delivered, then shipping and storage costs are reduced, but solvent flash point and VOC content become critical constraints

Engineering Contradiction:
Improveconcentration of cyclohexanone oximeVSAvoidflash point and VOC content
Core Design Contradiction:
Quantity of substanceVSObject-affected harmful factors

Solution Approach 1:

The patent optimizes the concentration parameter of cyclohexanone oxime in the range of 20-90 mass percent, achieving concentrated solutions that reduce shipping and storage costs while maintaining acceptable flash point and VOC content through careful formulation.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs fatty acids as a suitable solvent medium that enables concentrated delivery of cyclohexanone oxime. The fatty acid solvent system allows for high concentration formulations that are economically advantageous for shipping and storage, accepting the trade-off of managing flash point and VOC parameters through proper selection and formulation.

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

3Stability of the object's composition

If previously known solvents are used for cyclohexanone oxime, then solubility is achieved, but flash point decreases and VOC content increases

Engineering Contradiction:
Improvesolubility of cyclohexanone oximeVSAvoidflash point temperature and VOC content
Core Design Contradiction:
Stability of the object's compositionVSObject-affected harmful factors

Solution Approach 1:

The patent identifies and employs fatty acids as suitable solvents for cyclohexanone oxime, replacing previously known solvents that had unacceptable flash points and VOC content. The fatty acid solvent system provides the necessary solubility while meeting safety and environmental requirements for flash point and VOC content.

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 solution provides a stable, high-flash-point, low-VOC cyclohexanone oxime concentrate that effectively prevents skin formation in oil-based coatings, maintaining performance comparable to pure cyclohexanone oxime while reducing toxicity and regulatory risks, and optimizing shipping and storage costs.

Implementation Method 1

A clear, homogeneous solution of cyclohexanone oxime is achieved by dissolving it in suitable fatty acids

Methodology Applied
Scientific EffectSolubility: Solvation

Implementation Method 2

Anti-skinning agents are compounds that may be added to oil based coating materials to prevent the formation of skin or lumpy matter on the coating material as a result of oxidation during transportation or storage

Methodology Applied
Scientific EffectAnti-skinning: Oxidation

Data Source

PatentUS7875111B2Anti-skinning composition for oil based coating material
Publication Date: 2011.01.25 TROY CORP
  • US7875111B2 patent drawing
  • US7875111B2 patent drawing

AI summary

The invention provides anti-skinning compositions for use in manufacturing oil-based coating materials. The novel anti-skinning compositions are clear, homogeneous solutions of cyclohexanone oxime that can be prepared by dissolving cyclohexanone oxime in a suitable carboxylic acid or mixture of carboxylic acids. Suitable carboxylic acids include fatty acids, such as fatty acids of tall oil distillate. Surprisingly, the fatty acids are useful as delivery solvents over a useful range of temperatures and have desirable flash points. They are compatible with many oil-based coating materials. The anti-skinning compositions and manufacturing methods of the present invention are especially useful in the manufacture of oil-based paints containing metal carboxylate driers.