Cationic Dye Cyclodextrin Inclusion Complex for Hair Fastness

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Solution Overview

Problem

Cationic dyes exhibit unsatisfactory fastness to washing, light, shampooing, and rubbing, limiting their effectiveness in dyeing organic materials like keratin fibers and hair.

Innovation Solution

Development of cationic hair dyes with specific molecular structures and preparation processes that enhance their fastness properties, involving the reaction of dye intermediates with 3-amino-dihydro-thiophenone under controlled conditions to produce dyes with improved stability and depth of shade.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Illumination intensity

If conventional cationic dyes are used for dyeing organic materials, then brilliant shades are achieved, but fastness to washing is unsatisfactory

Engineering Contradiction:
Improveshade brillianceVSAvoidfastness to washing
Core Design Contradiction:
Illumination intensityVSReliability

Solution Approach 1:

The patent applies composite materials by combining the cationic dye molecule with a cyclodextrin host molecule to form an inclusion complex. The cyclodextrin cavity encapsulates the dye molecule, creating a composite structure that maintains the dye's brilliant coloring properties while the cyclodextrin shell provides enhanced fastness to washing, light, and mechanical stress.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The cyclodextrin molecule acts as an intermediary between the dye and the substrate (keratin fibers). It forms an inclusion complex with the dye and then interacts with the fiber surface, serving as a mediator that transfers the dye while providing protective encapsulation. This intermediary structure enables both brilliant shade deposition and improved fastness properties.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Ease of manufacture

If conventional cationic dyes are used for dyeing, then coloration is achieved, but fastness to light and mechanical stress is poor

Engineering Contradiction:
Improvedyeing effectivenessVSAvoidfastness to light and rubbing
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent creates a composite inclusion complex where the cyclodextrin host and cationic dye guest form a stable association. This composite structure provides both the ease of manufacture through simple mixing and the improved reliability by protecting the dye from light degradation and mechanical stress during use.

Inventive Principle:
Principle #40Composite materials

3Ease of operation

If standard cationic dyes are applied to keratin fibers, then coloring is achieved, but fastness to shampooing is unsatisfactory

Engineering Contradiction:
Improvedyeing simplicityVSAvoidfastness to shampooing
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The cyclodextrin inclusion complex serves as an intermediary that facilitates easy application to keratin fibers while providing protection during shampooing. The complex can be easily applied through conventional dyeing methods, and the cyclodextrin shell protects the dye from removal during shampooing, maintaining both ease of operation and improved reliability.

Inventive Principle:
Principle #24Intermediary (Mediator)

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 resulting dyes demonstrate excellent fastness to washing, light, and mechanical stress, providing deeper, longer-lasting color on keratin-containing fibers and hair.

Implementation Method 1

The dyes of formula (1) are suitable for dyeing organic materials, such as keratin-containing fibers, wool, leather, silk, cellulose or polyamides

Methodology Applied
Scientific EffectAdsorption: Adsorption

Implementation Method 2

Cationic dyes can be used for the dyeing of organic material, for example keratin, silk, cellulose or cellulose derivatives

Methodology Applied
Scientific EffectElectrostatic attraction: Ion Repulsion/Attraction

Data Source

PatentEP2124873B1Cationic dyes
Publication Date: 2016.01.06 BASF SE
  • EP2124873B1 patent drawing
  • EP2124873B1 patent drawing
  • EP2124873B1 patent drawing

AI summary

Disclosed are dyes of Formula (I) wherein D is the radical of anthraquinone, acridine, azo, azomethine, hydrazomethine, benzodifuranone, coumarine, diketopyrrolopyrrol, dioxaxine, diphenylmethane, formazane, indigoid, indophenol, naphtalimide, naphthaquinone, nitroaryl, merocyanine, methine, oxazine,perinone, perylene, pyrenequinone, phtalocyanine, phenazine, quinoneimine, quinacridone, quinophtalone, stilbene, styryl, triphenylmethane, xanthene, thiazine dye and thioxanthene dye; Q is C 1-C 30alkylene, -C 2-C 12alkenylene, C 5-C10arylene-, C 5-C 10cycloalkylene-or -C 1- C 10alkylene(C5-C10arylene)-which may be interrupted and/or terminated at one or both ends by one or more than one -O-, -S-, -N=, -N(R 1)-, SO2, -(CH 2CH 2-O) 1-5-, -(CH 2CH 2CH 2-O) 1-5-, -C(O)-, -C(O)-C1-C12alkenylene, -C(O)O-, -OCO-, AN+ R 1 R 2, -CON(R 1)-, -C(NR1R2) 2-, -(R1)NC(O)-, -CSR1-or an optionally substituted, saturated or unsaturated, fused or non-fused aromatic or nonaromatic (hetero)cyclic) bivalent radical optionally comprising at least one heteroatom; -O-; -S-; -N(R1)-; SO2; -(CH2CH2-O) 1-5-; -C(O)-; -C(O)-C1-C12alkenylene; -C(O)O-, -OCO-;B N+ R 1 R