Chromene Compound for Neutral Tint Photochromic Lenses

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Current chromene compounds used in photochromic spectacle lenses face issues with initial coloration, fading speed, durability, and color stability, particularly when mixed with other photochromic compounds, leading to unwanted tint changes over time.

Innovation Solution

A novel chromene compound with an indeno(2,1-f)naphtho(1,2-b)pyran structure incorporating a hetero ring with sulfur atoms at the 6- and 7-positions, enhancing electron donating ability, which improves color optical density, fading speed, and durability while maintaining a neutral tint.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If multiple photochromic compounds are mixed to achieve neutral tint, then color balance is improved, but durability and color stability deteriorate due to different repeat durability between yellow and blue compounds

Engineering Contradiction:
Improvecolor stabilityVSAvoidrepeat durability
Core Design Contradiction:
Stability of the object's compositionVSReliability

Solution Approach 1:

The patent merges the yellow and blue absorption characteristics into a single photochromic compound molecule. The compound contains both a yellow coloration development maximum (430-530 nm) and a blue coloration development maximum (550-650 nm) within the same molecular structure, eliminating the need to mix multiple compounds with different durability characteristics.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The patent creates a composite photochromic structure by combining multiple aromatic rings (indeno(2,1-f)naphtho(1,2-b)pyran core with additional fused or substituted aromatic systems) to generate multiple absorption maxima. This composite molecular architecture enables simultaneous yellow and blue coloration while maintaining uniform repeat durability.

Inventive Principle:
Principle #40Composite materials

2Productivity

If yellow compound has lower color development sensitivity than blue compound, then blue tint dominates during color development, but neutral tint balance is deteriorated

Engineering Contradiction:
Improvecolor development sensitivityVSAvoidneutral tint balance
Core Design Contradiction:
ProductivityVSStability of the object's composition

Solution Approach 1:

The patent applies local quality by creating distinct regions within the molecule that contribute differently to coloration. The molecular structure contains specific substituents and fused ring systems that locally enhance electron donating ability at different positions, creating optimized absorption characteristics at both yellow (430-530 nm) and blue (550-650 nm) wavelengths with balanced sensitivity.

Inventive Principle:
Principle #3Local quality

3Quantity of substance

If absorption end extends beyond 420 nm into visible range, then color optical density is improved, but initial coloration increases

Engineering Contradiction:
Improvecolor optical densityVSAvoidinitial coloration
Core Design Contradiction:
Quantity of substanceVSObject-generated harmful factors

Solution Approach 1:

The patent optimizes the absorption spectrum parameters by adjusting the molecular structure to position the absorption end at or near 420 nm (ultraviolet boundary) rather than extending deep into the visible range. This parameter optimization maintains high color optical density through enhanced electron donating ability while preventing excessive initial coloration by limiting visible light absorption in the unexposed state.

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 novel chromene compound achieves high color optical density, rapid fading, and improved durability, ensuring consistent neutral tint performance even after repeated exposure to light, with enhanced heat resistance and reduced initial coloration.

Implementation Method 1

Photochromism is the reversible function of a certain compound that it changes its color swiftly upon exposure to light including ultraviolet light such as sunlight or light from a mercury lamp and returns to its original color when it is put in the dark by stopping its exposure to light.

Methodology Applied
Scientific EffectPhotochromism: Photochromism

Implementation Method 2

incorporating a hetero ring with sulfur atoms at the 6- and 7-positions, enhancing electron donating ability, which improves color optical density, fading speed, and durability while maintaining a neutral tint

Methodology Applied
Scientific EffectElectron donating effect:

Data Source

PatentEP2684886B1Chromene compound
Publication Date: 2015.06.03 TOKUYAMA CORP
  • EP2684886B1 patent drawing
  • EP2684886B1 patent drawing
  • EP2684886B1 patent drawing

AI summary

A novel photochromic compound which develops a color of a neutral tint and has high color optical density, high fading speed and excellent durability. The present invention is a chromene compound having an indeno(2,1-f)naphtho(1,2-b)pyran structure as the basic skeleton in which a hetero ring having two hetero atoms including at least one sulfur atom is directly bonded to the 6-position and the 7-position of the indeno(2,1-f)naphtho(1,2-b)pyran structure via the hetero atom like the compound represented by the following formula (18).