NIR-Absorbing Squaraine Dye Composition for Wax-Soluble Phase Change Ink
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Solution Overview
Problem
Existing near-infrared (NIR) absorbing dyes are not wax soluble, limiting their application in phase change inks, which require dyes that can absorb radiation in the 700 nm to 1400 nm range and are stable at elevated temperatures.
Innovation Solution
Development of a dye compound with a squaric acid moiety and solubilizing moieties such as C10 to C70 hydrocarbyl groups, allowing the dye to be soluble in wax and absorb radiation in the 700 nm to 1400 nm range, suitable for use in phase change ink compositions.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Use of energy by moving object
If a squaric acid-perimidine moiety is used for NIR absorption, then radiation absorption in the 700 nm to 1400 nm range is achieved, but the dye compound becomes insoluble in wax
Solution Approach 1:
The patent applies local quality by introducing specific solubilizing groups (long-chain hydrocarbyl groups with 10-70 carbon atoms) at particular positions on the perimidine ring structure. This allows the molecule to have different properties in different regions: the squaric acid-perimidine core maintains NIR absorption capability while the appended hydrocarbyl chains provide wax solubility. The local modification of adding these solubilizing moieties resolves the contradiction between maintaining the NIR-absorbing core structure and achieving solubility in the wax matrix.
Solution Approach 2:
The patent creates a composite molecular structure by combining the squaric acid-perimidine chromophore (for NIR absorption) with long-chain hydrocarbyl solubilizing groups. This composite approach integrates two functional components into a single molecule: the chromophoric core that absorbs NIR radiation and the hydrophobic tails that interact with the wax matrix. This composite structure simultaneously achieves both NIR absorption and wax solubility, resolving the technical contradiction.
2Ease of operation
If phase change ink is used for inkjet printing, then solid-phase ink can be ejected as liquid droplets, but the dye must remain stable at elevated temperatures
Solution Approach 1:
The patent applies parameter changes by carefully selecting and optimizing the physical and chemical parameters of the dye molecule. The long-chain hydrocarbyl groups (C10-C70) are specifically chosen to provide appropriate melting point depression and thermal stability. These parameter adjustments allow the dye to remain stable at the elevated temperatures required for phase change printing (typically 60-100°C) while still being soluble in the wax matrix at operating temperatures. The parameter optimization of chain length and structure enables the dye to withstand the thermal cycling inherent in phase change inkjet printing.
3Use of energy by moving object
If known perimidine couplers are used, then NIR absorption is achieved, but the compounds are not soluble in wax-based phase change inks
Solution Approach 1:
The patent applies segmentation by dividing the perimidine coupler structure into distinct functional segments: the squaric acid-perimidine core segment that provides NIR absorption, and separate long-chain hydrocarbyl segments (10-70 carbon atoms) that provide wax solubility. This segmentation allows each part of the molecule to independently perform its designated function. The core segment maintains the NIR-absorbing properties of known perimidine couplers, while the appended hydrocarbyl segments provide the solubility in wax-based phase change inks that is lacking in conventional perimidine dyes.
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 dye compound is thermally stable, enabling its use in high-temperature print-head systems and providing NIR absorption, enhancing the performance of phase change inks in inkjet printers and other applications.
Implementation Method 1
A property of the dye compound is that it absorbs radiation having a wavelength in the range of about 700 nm to about 1400 nm
Data Source
AI summary
A dye compound of formula 1:where R and R′ are substituents independently selected from the group consisting of a hydrogen atom, C1 to C4 alkyl and a solubilizing moiety comprising a substituted or unsubstituted C10 to C70 hydrocarbyl group. At least one of R and R′ is not a hydrogen atom or C1 to C4 alkyl. R″ and R′″ can be independently selected from the group consisting of a hydrogen atom, C1 to C6 alkyl groups or halogens; and X is a squaric acid moiety. A property of the dye compound is that it absorbs radiation having a wavelength in the range of about 700 nm to about 1400 nm.