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Reactive Dyes… General Structure Has a Reactive Group Which Are Adsorbed on to the Cellulose and Than Reacted with the Fiber to Form Covalent Bonds

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Reactive Dyes… General Structure Has a Reactive Group Which Are Adsorbed on to the Cellulose and Than Reacted with the Fiber to Form Covalent Bonds Reactive Chemistry TECHNICAL INFORMATION Murat ŞAHİNLİ 12.11.2015 Cellulose… Cellulose structure Reactive dyes… General structure has a reactive group which are adsorbed on to the cellulose and than reacted with the fiber to form covalent bonds. Chromophore Bridging RG Reactive group Functional groups Reactive dyes… General structure has a reactive group which are adsorbed on to the cellulose and than reacted with the fiber to form covalent bonds. Chromophore Bridging RG Functional groups Shade Fastness Fastness Dischargeability Levelness Fixation Substantivity Application temperature Solubility Application temperature Reactive dyes… General reaction When put fabric and dye into the water; Cellulose: Cell-OH Cell-O¯ Electrostatic repulsion because of Dye: the negative charges HO3S-Dye-X X-Dye-SO3¯ With addition of salt: Cell-O¯ ⁺ Na Reduce the repulsion X-Dye-SO3¯ ⁺ Na Reactive dyes… General reaction After addition alkaline and linking with covalent bond; Thanks to covalent bond X-Dye-SO3¯ ⁺ Na + Na ⁺ ¯O-Cell Linking much more resistant to the usual conditions of use than the ( Soda ash, caustic …) physicochemical bond between direct dyes and cellulose. Na ⁺ ¯O3S – Dye –O-Cell + NaX Bond type App. Relative strength Covalent 30.0 Ionic 7.0 Hydrogene 3.0 Other 1.0 Intermolecular Reactive dyes… Description of dyeing mechanism Exhaustion of dye in presence of electrolyte by adsorption Fixation under the influence of alkali Wash off the unfixed dye from material surface T1: Addition of alkali and start of the fixation Reactive dyes… Exhaustion The reactive dyes is adsorbed onto the cellulose surface and than diffuses into the fiber. This phase is fully reversible. Dye molecules are in equilibrium between fiber and dyebath. Any change in bath composition affect the equilibrium [F] Dyebath [F] Cellulose So; affect the Substantivity [F] Cellulose S= [F] Dyebath Reactive dyes… Substantivity: Influencing parameters pH Electrolyte Temperature conc. Dye conc. Type of fiber Dye Liquor Substantivity affinity ratio Reactive dyes… Substantivity: Influencing parameters Standart affinity of dye; Like substantivity; is a measure for the distribution of a dye between fiber and dyebath. Unlike substantivity; affinity is constant at dyeing conditions, it is dye-spesific characteristic. The number of conjugated double Substantivity bonds in chromophore High affinity for cellulose (Direct dye) Low affinity for cellulose (Acid dye) Reactive dyes… Substantivity: Influencing parameters Electrolyte Concentration; Electrolyte conc. Anion-anion repulsion Substantivity Direct dyes; high affinity, require 5-10 g/lt salt Reactive dyes; medium to low affinity, require 40-100 g/lt Reactive dyes… Substantivity: Influencing parameters pH of dyebath; OH¯ Cell-OH Cell-O¯ + H2O H⁺ As the pH increases, the cellulose carries more and more negatively charge. The amount of the OH ion in the dye bath increases. pH Substantivity 7 8 9 Cell-O¯ (in the fiber) 10 RS: 11 OH¯ (in the dyebath) 12 13 Without alkaline addition Reactive dyes… Substantivity: Influencing parameters Dye concentration; Because of the limited adsorption capacity of fiber surface; [F] Cellulose S= [F] Dyebath Dye concentration Substantivity Surface saturation occurs later with high affinity dyes than low affinity dyes so, the greater influence on substantivity of low affinity dyes Reactive dyes… Substantivity: Influencing parameters Dyeing temperature; At 80⁰C, speed of diffusion of a dye in cellulose is higher than at 40⁰C. Dyeing equilibrium is therefore achieved much more rapidly at 80⁰C than 40⁰C. Temperature Substantivity Subsantivity seems to be lower at 40⁰C than at 80 ⁰C, but in fact it is not. Reactive dyes… Substantivity: Influencing parameters Liquor ratio; The Liquor ratio increases, the probability of contact between the dye molecules and the fiber surface decreases. Liquor ratio Substantivity Don’t forget that the decrease is also related to : Dye concentration Dye own affinity So; Reactive dyes… Substantivity: Influencing parameters Liquor ratio; Dye concentration (L.R. 10:1=%100) Affinity of the dye Dye :C.I. Reactive Red 180 Dye concentration :3% Electrolyte :50 g/lt NaCl Electrolyte :50 g/lt NaCl Dyeing temperature :40⁰C Dyeing temperature :40⁰C Reactive dyes… Substantivity: Influencing parameters Fiber type; Although the fiber structure has some minor effect on substantivity, we will see differences e.g.; Mercerized cotton dyes to a much deeper shade than non-mercerized It is merely the result of different optical properties: mercerized cotton has a circular cross section,which allows better light penetration, less random light reflection. Therefore, mercerized cotton can be much more easily penetrated by photons, thus a larger proportion of coming light is selectively adsorbed and this means higher color saturation. Raw cotton Mercerised and stretched cotton Reactive dyes… Diffusion rate: Influencing parameters But fiber type has a significant effect on Diffusion Rate… Fiber type Dyeing temperature Size and shape of dye molecule Subsantivity of dye molecule Electrolyte concentration in the bath Dye concentration Reactive dyes… Diffusion rate: Influencing parameters Adsorption equilibrium diffusion Dye uptake phase consist of successive states of equilibrium. Dye repeatedly makes brief stops on the crystallite walls Diffusion rate of a dye , decides its speed of exhaustion Reactive dyes… Diffusion rate: Influencing parameters So, speed of diffusion; . Speed of exhaustion . Levelness of dyeing . Fixation . Fastness properties Reactive dyes… Diffusion rate: Influencing parameters Fiber type; Cellulose Viscose Modal Crystalline regions Such a large dye molecule can not diffuse into the Viscose is still stiff at 40-50⁰C, while at higher highly oriented and tightly packed crystallites. temperatures (60-80⁰C ) the fibres mobility allows Dyeing therefore proceeds at the outer walls . the fibre bundle open. Reactive dyes… Diffusion rate: Influencing parameters When cotton is mercerized; Fiber induces a higher orientation of crystallites, this should reduce the diffusion rate but; A large portion of of intermicellar spaces of the cotton is dissolved and extracted by alkaline. Large molecules can be penetrated more easily to the empty spaces so; Mercerized cotton swells dye more than non-mercerized Diffusion speed of a dye is much higher (Despite high orientation) Higher speed of exhaustion Stronger shade Raw cotton Mercerized cotton Reactive dyes… Diffusion rate: Influencing parameters Temperature; Temperature Diffusion rate Temperature has by far the greatest effect on diffusion So greatest effect on; . Migration rate . Washing-off . Levelness Reactive dyes… Diffusion rate: Influencing parameters Size and shape of dye molecule; Molecule size Diffusion rate Larger and bulkier dye molecules have a much slower rate of diffusion than smaller ones Reactive dyes… Diffusion rate: Influencing parameters Size and shape of dye molecule; Reactive Blue 15 (Turquoise) Reactive Red 198 > MCT/VS Bifunctional Reactive Dye Phthalocyanine Poor; Chromophore tents to . Diffusion Diffusion rate: be square and very . Levelling Reactive Red 198 > Reactive Blue 15 bulk in the structure. Washing-off properties Reactive dyes… Diffusion rate: Influencing parameters Substantivity; It promotes adsorption equilibrium but impairs diffusion speed. High subsantivity dyes while exhausting more completely from the dye bath, diffuse, migrate and level more slowly. e.g.; Everzol Yellow LX Reactive dyes… Diffusion rate: Influencing parameters Electrolyte concentration; Electrolyte Conc. Subsantivity Diffusion rate There is a small exception to this rule; At very low electrolytes concentration adding a trace of electrolytes to the dye bath helps to improve diffusion. This exception is rarely encountered in real-life dyeing operation. Reactive dyes… Fixation T1: Addition of alkali and start of the fixation Reactive dyes… Fixation Alkali is necessary for; the dyestuff reaction with the fiber (heterocyclic type) formulation of reactive site and reaction of dyestuff with the cellulosic fiber (vinylsulfone type) Increasing alkali ……………………………… Decreasing reactivity Soda ash Soda ash/Caustic soda Reactive dyes… Fixation Then, What is the meaning of heterocyclic or vinylsulfone…? How is the reactive dyes chemical structure…? Reactive dyes… Fixation; Dye chemical structure Chromophore Bridging RG monofunctional Reactive group Functional groups ; providing water solubility conjugated Chromophore Bridging RG RG bifunctional isolated RG Bridging Chromophore Bridging RG bifunctional Reactive dyes… Reactive group chemistry; Fixation; Dye chemical structure Monochlortriazin (MCT) Monofluortriazine (MFT) Difluorochlorpyrimidine (FCP) Cl N rest N rest F N N N N N N Cl F F •Low reactivity •Medium to high reactivity •High reactivity •Sensitive to acid •Sensitive to acid •Stable to acid and alkaline •Stable to alkaline •Stable alkali to alkaline •Splitting with peroxide and light •May generate AOX •AOX free •AOX free Vinyl sulfone (VS) Dichlorchinoxaline (DCC) Chromophore N Cl SO2-CH=CH2 Bridge •Medium reactivity Cl N •Stable to acid •High reactivity •Sensitive to alkaline •Sensitive to acid •Dischargeable, stripping is possible •Not hydrolysable AOX •AOX free Increasing Reactivity Reactive dyes… Fixation Hot-dyeing dyes Cold-dyeing dyes Substantivity Everzol dyes Reactivity Reactive dyes… Fixation Reactive dyes… Fixation Everzol Yellow NPN Everzol Red LX Reactive dyes… Fixation Dye-fiber reaction: 1. Nucleophilic substitution
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