Photochromic Compound Structure for High-Temperature Color Stability

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Existing T-type photochromic compounds exhibit a trade-off relationship between fading rate and color optical density, leading to decreased color optical density under high temperatures, and have limited durability and temperature dependence.

Innovation Solution

A photochromic compound with a molecular structure where at least two monovalent photochromic basic structural groups containing a T-type photochromic moiety are bonded via a non-SO aromatic ring, restricting molecular motion and reducing temperature dependence.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Illumination intensity

If the blending amount of T-type photochromic compound is increased to maintain color optical density under high temperature, then color optical density is improved, but cost increases and dissolubility deteriorates

Engineering Contradiction:
Improvecolor optical densityVSAvoiddissolubility
Core Design Contradiction:
Illumination intensityVSQuantity of substance

Solution Approach 1:

The invention changes the molecular structure parameters of the photochromic compound by introducing specific substituent groups (electron-withdrawing groups at positions 6 and 7 of the indeno[2,1-f]naphtho[1,2-b]pyran core) to improve thermal stability and maintain color optical density without increasing blending amount

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite molecular structure combining the indeno[2,1-f]naphtho[1,2-b]pyran photochromic core with specific substituent groups (such as fluorine atoms, cyano groups, or carbonyl groups) to achieve enhanced thermal stability and solubility properties simultaneously

Inventive Principle:
Principle #40Composite materials

2Illumination intensity

If thermal stability in colored state is improved to achieve high color optical density under high temperature, then color optical density is improved, but fading rate decreases

Engineering Contradiction:
Improvecolor optical densityVSAvoidfading rate
Core Design Contradiction:
Illumination intensityVSSpeed

Solution Approach 1:

The invention applies local quality modification by introducing electron-withdrawing substituent groups at specific positions (6 and 7) of the photochromic core molecule, which locally stabilizes the colored state without affecting the overall fading mechanism, thus achieving both high color optical density and fast fading rate

Inventive Principle:
Principle #3Local quality

3Reliability

If substituents are incorporated to achieve desired photochromic properties and color tones, then photochromic properties are improved, but temperature dependence increases

Engineering Contradiction:
Improvephotochromic propertiesVSAvoidtemperature dependence
Core Design Contradiction:
ReliabilityVSTemperature

Solution Approach 1:

The invention carefully selects and positions specific electron-withdrawing substituent groups (F, CN, C=O) at positions 6 and 7 of the photochromic core, which changes the electronic parameters of the molecule to reduce temperature dependence while maintaining desired color tones and photochromic properties

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 compound maintains high color optical density and stable color tones under high temperatures while improving photochromic durability by minimizing temperature-induced fading.

Implementation Method 1

Photochromic compounds are compounds that can undergo a reversible transformation between two isomers with different absorption spectra when irradiated with ultraviolet-containing light such as sunlight or light from a mercury lamp

Methodology Applied
Scientific EffectPhotochromism: Photochromism

Implementation Method 2

Upon isomerization from the color developed state to the decolored state (fading reaction), some photochromic compounds return to the original colorless state not only by light with a specific wavelength but also by heat

Methodology Applied
Scientific EffectThermal relaxation:

Data Source

PatentUS12570894B2Photochromic compound and curable composition containing the photochromic compound
Publication Date: 2026.03.10 TOKUYAMA CORP
  • US12570894B2 patent drawing
  • US12570894B2 patent drawing
  • US12570894B2 patent drawing

AI summary

A photochromic compound of the present invention comprises at least two monovalent photochromic basic structure groups PC including a T-type photochromic moiety, the photochromic basic structure groups being bonded to an organic group having a non-SO aromatic ring containing neither a sulfur atom nor an oxygen atom.