Tricyclodecane Dimethanol Composition for Coating Solubility

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Solution Overview

Problem

Tricyclodecane dimethanol compositions used in polyester resin production for coatings face challenges with crystallization and solvent resistance, requiring a method to control C11-12 diol compound content for improved solubility and chemical resistance.

Innovation Solution

A tricyclodecane dimethanol composition with controlled C11-12 diol compound content, prepared through a hydroformylation and hydrogenation process using a rhodium-containing catalyst and organophosphorus compound, achieving a balance of solubility and solvent resistance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If TCDDM is prepared by conventional hydroformylation and hydrogenation, then the production process is simple, but the resulting polyester resin has poor solubility in organic solvents and water

Engineering Contradiction:
Improveproduction process simplicityVSAvoidsolubility of polyester resin
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The invention changes the compositional parameters of TCDDM by controlling the content of specific isomers (3,8- and 3,9-isomers at 60-80 mol%) and limiting C11-12 diol compounds (4-20 wt%). This compositional parameter adjustment improves the solubility of polyester resin in organic solvents and water while maintaining the conventional hydroformylation and hydrogenation process

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite composition of TCDDM containing multiple isomers (3,8-isomer, 3,9-isomer, and other isomers) in specific ratios, along with controlled amounts of C11-12 diol compounds. This composite structure at the molecular level enhances the overall solubility performance of the polyester resin

Inventive Principle:
Principle #40Composite materials

2Ease of manufacture

If TCDDM is prepared by conventional hydroformylation and hydrogenation, then the production process is simple, but the coating film shows poor solvent resistance and corrosion resistance

Engineering Contradiction:
Improveproduction process simplicityVSAvoidsolvent resistance and corrosion resistance of coating film
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The invention adjusts the compositional parameters of TCDDM by controlling isomer distribution (3,8- and 3,9-isomers at 60-80 mol%) and C11-12 diol compound content (4-20 wt%). These parameter changes result in polyester resins that form coating films with excellent solvent resistance and corrosion resistance while keeping the production process simple

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention utilizes C11-12 diol compounds, which are typically considered impurities or by-products of the hydroformylation process, and converts them into beneficial components. By controlling their content at 4-20 wt%, these compounds contribute to the solvent resistance and corrosion resistance of the coating film without requiring additional purification steps or expensive raw materials

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

3Manufacturing precision

If the content of C11-12 diol compounds is reduced to improve purity, then the polyester resin purity increases, but the solubility in organic solvents and water decreases

Engineering Contradiction:
Improvepurity of polyester resinVSAvoidsolubility in organic solvents and water
Core Design Contradiction:
Manufacturing precisionVSReliability

Solution Approach 1:

The invention inverts the conventional approach by setting the C11-12 diol compound content to 4-20 wt% rather than minimizing it. Combined with specific isomer distribution (3,8- and 3,9-isomers at 60-80 mol%), this parameter change simultaneously achieves high purity polyester resin and excellent solubility in organic solvents and water

Inventive Principle:
Principle #35Parameter changes

4Reliability

If the isomer composition of TCDDM is optimized to improve coating performance, then the solvent resistance improves, but the production complexity increases

Engineering Contradiction:
Improvesolvent resistance of coating filmVSAvoidproduction process complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The invention optimizes the isomer composition parameters (3,8- and 3,9-isomers at 60-80 mol%, with other isomers at 20-40 mol%) through control of hydroformylation and hydrogenation conditions. This parameter optimization achieves excellent solvent resistance in coating films while maintaining a relatively simple production process without requiring additional complex steps

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 composition enhances the solubility of polyester resins in organic solvents and water, while maintaining excellent solvent and corrosion resistance, making it suitable for coating metal substrates without compromising curing rate or strength.

Implementation Method 1

performing a hydroformylation reaction by introducing a catalyst composition including a rhodium-containing catalyst compound and an organophosphorus compound into a reactor, and by adding dropwise dicyclopentadiene under a mixed gas of hydrogen and carbon monoxide

Methodology Applied
Scientific EffectHydroformylation:

Implementation Method 2

performing a hydrogenation reaction of tricyclodecane dialdehyde obtained by the hydroformylation reaction in the presence of a hydrogenation catalyst

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Data Source

PatentUS11891354B2Tricyclodecane dimethanol composition and preparation method of the same
Publication Date: 2024.02.06 SK CHEMICALS CO LTD
  • US11891354B2 patent drawing
  • US11891354B2 patent drawing
  • US11891354B2 patent drawing

AI summary

Provided are a tricyclodecane dimethanol composition which may be suitably used in preparing a polyester resin exhibiting excellent solvent resistance and chemical resistance when forming a coating film and having excellent solubility in organic solvents or water, and a preparation method thereof.