Diacetylene Compounds for Thermoplastic Compatibility

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Solution Overview

Problem

Current diacetylene-based materials for multi-color applications lack compatibility with thermoplastics, leading to processability issues and phase separation, and do not effectively change color in response to irradiation for versatile imaging and printing solutions.

Innovation Solution

Development of novel diacetylene compounds with specific structural features, such as X-C≡C-C≡C-Y-(CO)n-QZ, which include alkylene groups and functional groups like esters, amides, and thioesters, that undergo color change upon irradiation, enhancing compatibility with thermoplastics and allowing for cross-linking and polymerization, thereby stabilizing the colored state.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If conventional diacetylene-based materials are used for multi-color applications, then color change capability is achieved, but compatibility with thermoplastics deteriorates leading to processability issues and phase separation

Engineering Contradiction:
ImproveprocessabilityVSAvoidcompatibility with thermoplastics
Core Design Contradiction:
Ease of manufactureVSStability of the object's composition

Solution Approach 1:

The patent modifies the chemical structure of diacetylene compounds by introducing specific functional groups (esters, amides, thioesters) and alkylene groups to change their physical and chemical parameters. This structural modification improves compatibility with thermoplastics while maintaining the color change capability upon irradiation.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite systems by combining modified diacetylene compounds with thermoplastic materials. The functional groups in the diacetylene compounds facilitate better integration with thermoplastics, preventing phase separation and improving overall material compatibility while retaining imaging functionality.

Inventive Principle:
Principle #40Composite materials

2Reliability

If conventional diacetylene materials are used, then color change upon irradiation is achieved, but resistance to phase separation deteriorates

Engineering Contradiction:
Improveresistance to phase separationVSAvoidcolor change response
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

By changing the chemical parameters of diacetylene compounds through functional group modification, the patent achieves both improved resistance to phase separation and maintained color change response. The specific structural features (alkylene groups, functional groups) are optimized to balance these two requirements.

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If simple diacetylene structures are used, then ease of synthesis is maintained, but cross-linking and polymerization capability deteriorates

Engineering Contradiction:
Improveease of synthesisVSAvoidcross-linking and polymerization capability
Core Design Contradiction:
Ease of manufactureVSStrength

Solution Approach 1:

The patent introduces specific functional groups at particular positions in the diacetylene molecular structure. These localized modifications (esters, amides, thioesters) provide cross-linking and polymerization capability without requiring complete structural redesign, thus maintaining relative ease of synthesis while enhancing material strength and stability.

Inventive Principle:
Principle #3Local quality

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 diacetylene compounds demonstrate improved compatibility with thermoplastics, enabling enhanced processability and resistance to phase separation, and exhibit reversible color changes upon irradiation, allowing for multi-color imaging and printing applications without the need for multicomponent mixtures.

Implementation Method 1

compounds of the invention are ethers, thioethers, amides or derivatives of carboxylic acids... which undergo color change upon irradiation

Methodology Applied
Scientific EffectPhotochromism: Photochromism

Implementation Method 2

because Z includes a C≡C bond, this can undergo cross-linking and/or polymerisation, thus locking the chain in the state that is coloured

Methodology Applied
Scientific EffectPhotopolymerisation: Photopolymerisation

Data Source

PatentEP2235591B1Polychromic substances and their use
Publication Date: 2012.02.22 DATALASE
  • EP2235591B1 patent drawing

AI summary

A compound which undergoes a colour change upon irradiation, and which has the general structure: X-C≡C-C≡C-Y-(CO)n-QZ wherein X is H, alkyl or -Y-(CO)n-QW; each Y is the same or a different divalent alkylene group; Q is O, S or NR; R is H or alkyl; W is H, alkyl or Z; each Z is the same or a different unsaturated alkyl group; and each n is 0 or 1.