Synthesis of a di‐(p‐sulphophenoxy)‐s‐triazine reactive dye and its application in wool fabric ink‐jet printing

Reactive dyes based on p‐sulphophenoxy‐s‐triazines were synthesised, characterised and applied to wool fabric by ink‐jet printing. The extent of dye‐fibre covalent bonding (% fixation) was measured on prints produced using different development methods. The most promising method to obtain high dye‐fibre fixation values was to interleave the printed wool with a pre‐wetted cotton fabric and store for 3 h. Steam fixation was also investigated but gave lower fixation values. The degree of dye hydrolysis vs time in the ink formulation was evaluated because ink stability is critical in commercial operation; a reformulated ink based on a phosphate buffer was found to improve ink stability.     

Green synthesis of reactive dye for ink‐jet printing

Chloropyrimidine‐based reactive dyes are reported as well suited to textile printing; however, nucleophilic aromatic substitution of chloropyrimidines with amino‐containing chromophores is slow and often suffers from poor yields. In this study, a novel and simple method was developed for the synthesis of chloropyrimidine‐based reactive dye under microwave irradiation. In addition, the dye was also synthesised by conventional heating for comparison, which took both the reaction time and yield into account. The progress of the synthesis reactions concerned were monitored using capillary electrophoresis and the purity of the dye obtained was assessed by thin‐layer chromatography. The structure of the synthesised trichloropyrimidine dye was confirmed by Fourier Transform–infrared spectroscopy and elemental analysis. It was found that the reaction rate of the nucleophilic aromatic substitution carried out under microwave irradiation was 4‐fold faster than that carried out under conventional heating, although the enhancement in product yield was modest. These results suggest that microwave irradiation is an effective technique for the synthesis of chloropyrimidine‐based reactive dyes. The synthesised chloropyrimidine dye was formulated into an ink and applied onto a wool fabric by ink‐jet printing. The printed fabrics were steamed at 102°C for 5‐25 minutes at 5‐minute intervals. Good K/S and rate of dye fixation were obtained, both of which improved with increasing steaming time. The prints obtained exhibited reasonably good light and wash fastness properties.     

Synthesis and application of KM‐type reactive dyes containing 2‐ethoxy‐4‐chloro‐s‐triazine

A new kind of hetero‐bifunctional reactive dye containing 2‐ethoxy‐4‐chloro‐s‐triazine, with better activity matching with β‐hydroxyethyl sulphone sulphate at a low fixation temperature, was successfully synthesised and characterised. An ethoxy group was designed to be introduced into triazine to increase the substantivity and the reactivity of the dyes. Thereby, the fixation of mono‐s‐chlorotriazine/hydroxyethyl sulphone sulphate (KM‐type) bifunctional reactive dyes on cotton was improved, and dyeing under mild conditions with high fixation was realised. Nineteen dyes with orange, red and blue colours were synthesised and characterised by UV‐Vis and infrared spectroscopy and mass spectrometry. Synthesised dyes were dyed at 60, 75 and 90°C, respectively. Exhaustion and reactivity for all of the ethoxy‐containing KM‐type dyes was over 90% at the optimal temperature, and fixation was over 87%, which was higher than the ethoxy‐free comparative dyes. The optimal fixation temperature of ethoxy‐containing dyes was initially reduced to 75°C, and then to 60°C. Compared with comparative dyes, the wash fastness and light fastness were basically unchanged, and the wet rub fastness of the H‐acid series was reduced by one grade.     

Modified 2,4‐difluoro‐5‐chloro‐pyrimidine dyes and their application in ink‐jet printing on wool fabrics

This paper describes the modification of three commercially available 2,4‐difluoro‐5‐chloropyrimidine dyes (Drimarene Brilliant Red K‐4BL, Drimarene Brilliant Blue K‐BL and Drimarene Golden Yellow K‐2R) by the reaction of the parent dye with 4‐hydroxybenzensulphonic acid sodium salt. Capillary electrophoresis was used to monitor both the course of the above reaction and to ascertain the dye stability of the dyes in an ink formulation. Inks prepared from the modified dyes showed much higher storage stability compared with the parent dye‐containing inks; this was confirmed by capillary electrophoresis analysis. Inks containing the modified dyes were printed on wool fabrics and diffusion/fixation achieved by ‘batching’ the prints at 25 °C; high fixation values were obtained for all three modified dyes. These prints exhibited excellent colour fastness to washing, rubbing and light, the former test confirming a high degree of dye–fibre covalent bonding.     

A custom ink‐jet printing system using a novel pretreatment method

A low‐cost and environmental‐friendly direct dye‐based ink‐jet printing system was developed. A novel ink‐jet pretreatment method was employed, in which the cationic fixing agent, Matexil FC‐ER, was applied as the colourless fixing ink and applied only on image areas of the fabric by ink‐jet printer. It was found that this new pretreatment method could more effectively enhance the colour strength and improve the wash fastness (greyscale ≥ 3) when compared with traditional exhaust application. The cross‐staining of non‐image areas of fabric was also apparently decreased using this new method. The light fastness of ink‐jet pretreated samples was slightly reduced as the presence of Matexil FC‐ER made dyes more sensitive to light.     

Photorealistic ink‐jet digital printing – factors influencing image quality,image stability and print durability

Digital cameras have now replaced film‐based cameras as the most popular method of still image capture. As a consequence, there has been a rise in growth of the photo‐realistic digital‐printer market as many amateur and professional photographers choose to produce their own hard copy images. The most popular digital printing technology for producing photo‐realistic images is currently drop‐on‐demand ink jet. There has been much research into key factors influencing the quality, stability and durability of images produced using this, and other, digital printing technologies. A key area of study in achieving photo‐realistic images from digital printing systems has been ink‐receivable layers and dye/pigment colorants, and most importantly compatibility between the two. As with any new technology it is important to achieve an acceptable standard of performance and, to this end, research work has been instigated by the International Standards Institute since the mid‐1990s, to achieve a set of standards appertaining to areas such as light fastness, water fastness, thermal stability, humidity fastness and pollution susceptibility. This paper reviews the current state regarding the aforementioned areas with respect to their influence on print quality, stability and durability.     

Use of a biomaterial as a thickener for textile ink‐jet printing

The feasibility of using chitosan as a thickener in the pretreatment print paste for textile ink‐jet printing was explored. An orthogonal analysis was used to determine the optimum conditions for using chitosan as a thickener in the pretreatment print paste and the effects of different process factors for achieving the best color yield in textile ink‐jet printing. With the help of the orthogonal analysis, the importance of different process factors was found to be in the order of (1) the amount of urea used, (2) the amount of chitosan used, (3) the amount of sodium bicarbonate used, and (4) the steaming time. On the basis of the results of the orthogonal analysis, the optimum conditions for using chitosan as a thickener for the pretreatment print paste were concluded to be 40 mL of chitosan, 10 g of urea, 8 g of sodium bicarbonate, and 5 min of steaming. According to an analysis of the results of different color fastness tests, chitosan could principally work as a pretreatment print paste thickener. However, the final color yield obtained from chitosan‐containing cotton fabrics depended greatly on the stage of the chitosan application. Nevertheless, the color fastness properties and the outline sharpness of the prints of cotton fabric were greatly improved by the chitosan treatment. A two‐bath chitosan treatment was developed to separate the chitosan from sodium bicarbonate and urea before it was padded onto the fabric surface to minimize the neutralization effect. On the basis of the results for the highest color yield obtained on the cotton fabric, it was confirmed that the two‐bath chitosan treatment was successfully developed. In addition, chitosan could impart higher antibacterial properties with a slight reduction in the tensile strength of the cotton fabric. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2008     

Synthesis and application of a novel,triphendioxazine‐based,phosphorus‐containing acid dye for wool

A novel phosphorus‐containing acid dye based on triphendioxazine was designed and synthesised from diphenylamine through a series of reactions. The dye has a navy‐blue colour, high molar extinction coefficient of 5.32 × 10⁴ l/mol·cm, and high substantivity for dyeing wool in a salt‐free, aqueous dyebath. A high exhaustion value of 98.2% on wool fabrics was recorded at 3% omf and a liquor ratio of 1:20. The wash fastness values of the acid dye, including colour change and staining on cotton and wool, were grades 5, 4 and 4–5, respectively. The dry and wet fastness are grades 4–5 and 4, respectively. In addition, light fastness reaches grades 6–7 at 3% omf dye concentration. These dye properties are better than those of commercial triphendioxazine dyes, for example, CI Direct Blue 106 and CI Reactive Blue 198, under analogous dyeing conditions.     

Synthesis and characterization of hetarylazo disperse colorants: Preparation and properties of conventional and microemulsified inks for polyester ink‐jet printing

The synthesis and characterization of three hetarylazo disperse colorants are described. These compounds were used for the preparation of conventional inks and/or oil‐in‐water microemulsions (microemulsified dyes). The viscosity, conductivity, surface tension, and pH of these inks were studied over a period of time and discussed with respect to their structure. The particle size and particle size distribution of a representative microemulsion were compared to those of a corresponding conventional ink. The measured properties were compared to the properties of commercially available inks. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010     

Synthesis of low viscosity,fast UV curing solder resist based on epoxy resin for ink‐jet printing

A novel photosensitive low viscosity epoxy resin was synthesized by polyethylene glycol (PEG)‐modified bisphenol‐A epoxy resin (E51). The resin was modified by ethylene glycol, diethylene glycol, and different molecule weights (200,300,400) PEGs to optimize the minimum viscosity. FTIR was used to determine molecule structure. Cationic photoinitiator (UVI‐6976) mixed with modified resin (10 wt %), was utilized to boost the resin curing under UV light. The curing degree was beyond 90% within 40 s and the whole process was monitored by photo‐DSC. The modified resin diluted with ethylene glycol diglycidyl ether, was screen printed onto polyimide and polyethylene terephthalate substrate, and the properties of solder mask were up to China printed circuit association standard. The solder resist also meet all requirements under ink‐jet printing technology as the viscosity is under 60 mPa·s and the curing duration is <1 min. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013     

Colour management of a low‐cost four‐colour ink‐jet printing system on textiles

A low‐cost four‐colour (RBYK) dye‐based ink‐jet printing system for textiles was introduced in this study, in which red and blue inks were employed instead of the magenta and cyan inks used in half‐tone printing. The basis of a colour‐management system for this device was developed by determining the mapping between XYZ tristimulus values of output colours and the digital RBYK values using polynomial transforms. A second‐order equation was found to give the best performance with an average characterisation error of under 7 CIELAB units.     

Influence of nano‐coated pigment ink formulation on ink‐jet printability and printing accuracy

Pigment ink was formulated with nano‐coated pigment dispersion, prepared via mini‐emulsion polymerization. To study the effect of nano‐coated pigment, surfactant and humectant on ink‐jet printability, the trajectory of droplets with different pigment ink composition was monitored. The effect of ink formulation on the accuracy of printing process of the pigment ink was discussed by study on line width and edge contour of printed patterns. Experimental results indicated that the additives and properties of the pigment ink had a great influence on droplet formation and precise positioning of the printed patterns. The optimal composition for the pigment ink as following: nano‐coated pigment dispersion was 20% w/w, surfactant (S‐465) was 1.5% w/w, humectant (diethylene glycol) was 30% w/w and defoamer (FB‐50) was 0.1% w/w. The prepared pigment ink exhibited excellent freeze–thaw, thermal and centrifugal stability. In addition, the optimal formula was beneficial to form a stable droplet and obtain high precision patterns.     

Polymerization of fluoroacrylate and guar gum copolymer as a new pretreatment paste for ink‐jet printing of polyester

A novel pretreatment paste containing fluoroacrylate copolymer and modified Guar Gum was carried out on the polyester fabric to provide partial water repellency and printability after inkjet printed with water‐based disperse dye inks. The stable fluorinated pastes were prepared via miniemulsion polymerization of fluoroalkyl acrylates, styrene, 2‐ethylhexyl acrylate, and modified guar gum in the presence of AIBN as initiator, CTAB and polyoxyethylene polyaryl ether as surfactants under suitable reaction conditions. In the analysis of monomer conversion and particle size, the highest polymerization rate with smallest particle size was obtained with increasing concentration of surfactants and initiator but the decreasing degree of substitution of guar gum to imply stronger interactions between fluoroacrylate monomers, hydroxyl groups of modified guar gum and EO units of nonionic surfactants. The 30% of stock fluorinated paste with urea concentration of 6% provided the prints with highest K/S value, satisfactory edge acuity and least color difference between front and back sides of the fabric to show more transparency. The rating 80 of water repellency tested on the best treated polyester fabric demonstrated stain proof properties after sprayed with water and dried. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009     

Synthesis and characterization of poly(arylene ether s‐triazine)s containing alkyl‐, aryl‐ and chloro‐substituted phthalazinone moieties in the main chain

Soluble and heat‐resistant polymers have great potential for use as processable, high‐temperature polymeric materials. In this study, four types of new poly(arylene ether s‐triazine)s containing alkyl‐, aryl‐ and chloro‐substituted phthalazinone moieties in the main chain were prepared through direct solution polycondensation of 2,4‐bis(4‐fluorophenyl)‐6‐phenyl‐s‐triazine with each of methyl‐, phenyl‐ and chloro‐substituted phthalazinones. A key feature of these polymers is the incorporation of phthalazinone and side groups into the poly(arylene ether s‐triazine) backbone to endow them with good solubility while maintaining other attractive properties. The polymers were obtained in high yields, and had inherent viscosities ranging from 0.38 to 0.55 dL g^?1. Their structure was characterized using Fourier transform infrared and NMR spectra and elemental analysis. The polymers were almost amorphous, and soluble in N‐methyl‐2‐pyrrolidone, pyridine, N,N‐dimethylacetamide, hot N,N‐dimethylformamide and sulfolane. Tough and nearly transparent films obtained by direct solution casting exhibited good mechanical properties. The resulting polymers displayed glass transition temperatures ranging from 255 to 265 °C and thermal decomposition temperatures for 10% mass loss ranging from 476 to 599 °C, according to differential scanning calorimetry and thermogravimetric analysis, respectively. The reactivity of substituted phthalazinones in nucleophilic displacement reactions and the effect of the side groups on the physical properties of the polymers were also investigated. The results obtained revealed that such s‐triazine‐containing polymers possessed good solubility while maintaining acceptable thermal stability and high mechanical strength with the incorporation of alkyl‐, aryl‐ and chloro‐substituted phthalazinone moieties into their backbones, which makes them an attractive series of high‐performance structural materials. Copyright © 2010 Society of Chemical Industry     

Disperse ink‐jet inks: properties and application to polyester fibre

Water‐based ink‐jet inks were prepared using press cake samples of two commercially available azo disperse dyes. The suitability of the inks for printing polyester fabric was evaluated via measurement of surface tension, conductivity, viscosity, pH and particle size distribution. Inks prepared by the proposed method fulfill most requirements for an ink‐jet ink depending on the colorant structure, the dispersing agent and the alcohol used. The inks were applied to polyester fabric by both printing and dyeing and the fastness of the ensuing coloured samples was assessed. The fastness properties of the dyed and printed polyester samples were found to be very good to excellent and generally meet accepted customer requirements. Oil‐in‐water microemulsions containing the same colorants were also prepared. Their properties, which are crucial to the suitability for ink‐jet ink, were compared with those of the conventionally prepared inks and were found to be improved, with the exception of conductivity, while surface tension remained within acceptable values.     

Ink‐jet printing of nylon fabric using reactive dyestuff

This study discusses ink‐jet printing of nylon fabric with reactive dyestuff. Specifically, this paper investigates the impact of the concentration levels of pretreatment paste on fabric permeability, and examines the influence of various acid agents, hygroscopic agents and different processing conditions on colour yield. Results show that ink‐jet printing displayed excellent wet fastness in repeated wash testing. This study used four reactive dyestuffs, cyan, magenta, yellow and black, all of which achieved both wash fastness and crock fastness of grade 4.     

Synthesis of an amino coumarin‐based fluorescent reactive dye and its application to wool fibres

The objective of the current study was to introduce the coumarin structure into a conventional reactive dye system. A fluorescent reactive dye was synthesised based upon 7‐amino‐4‐methylcoumarin. The dye was obtained by a multi‐step sequence initiated by displacement of a chlorine group from 2,4,6‐trichloro‐1,3,5‐triazine using H‐acid. Diazo coupling of 3‐aminobenzenesulphato‐ethylsulphone to this adduct, followed by a second chlorine displacement using aminomethylcoumarin completed the sequence. The fluorescent dye and the non‐fluorescent precursor were characterised by mass spectrometry, infrared spectroscopy and capillary electrophoresis. The newly synthesised dye was applied to wool fibres using an exhaust dyeing method. The exhaustion, fixation and total efficiency values were calculated by ultraviolet–visible spectrophotometric analysis of the dyebath. The synthesised red dye presented high values for exhaustion, fixation and total efficiency on the wool fibres. The novel dye, after its application to the wool fibres, exhibited fluorescence under an ultraviolet light. This feature confirmed that the novel dye retained the inherent characteristic feature of fluorescence on the wool fibres. The dyed wool fibres exhibited level 4–5 of light fastness when compared with international wool light fastness standards.     

4‐chloro‐3‐methylphenyl methacrylate copolymers with 2,4‐dichlorophenyl methacrylate: Synthesis,characterization, and antimicrobial activity

4‐Chloro‐3‐methylphenyl methacrylate (CMPM) and 2,4‐dichlorophenyl methacrylate (2,4‐DMA) were synthesized by reacting methacryloyl chloride with 4‐chloro‐3‐methylphenol (CMP) and 2,4‐dichlorophenol (2,4‐DP), respectively. Homo and copolymers of CMPM and 2,4‐DMA were obtained from different monomer feed ratios, using 2,2′‐azobisisobutyronitrile as initiator in toluene at 70°C. IR‐spectroscopy was employed to characterize the resulting homo and copolymers. Copolymer compositions were determined by ultraviolet (UV) spectroscopy. Fineman–Ross method was used to calculate the reactivity ratios of the monomers. Average molecular weight and polydispersity index were obtained by gel permeation chromatography (GPC). Thermogravimetric analyses (TGA) and differential thermal analysis (DTA) of copolymers were carried out under a nitrogen atmosphere. Antimicrobial effects of the homo and copolymers were also investigated for various microorganisms such as bacteria, fungi, and yeast. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 100:439–448, 2006     

Syntheses of polymeric dispersants for pigmented ink‐jet inks

Drop‐on‐demand ink‐jet inks made from dyes usually show poor light fastness and poor water fastness. Therefore, many researchers have introduced pigments into ink‐jet inks to overcome the defects of dye‐based ink. Pigmented ink needs sophisticated technology which disperses the pigments stably in low viscosity. Thus, adequate dispersants are essential to achieve stable dispersions of pigments for ink‐jet inks. This study describes syntheses of dispersants, properties of formulations and comparisons of performance with an existing ink to assess their suitability for commercial application.     

Synthesis and physicochemical properties of poly[2‐(2‐chloro‐1‐methylbut‐2‐en‐1‐yl)aniline] obtained with various dopants

Highly soluble polyaniline was synthesized from a newly designed aniline derivative, namely 2‐[2‐chloro‐1‐methylbut‐2‐en‐1‐yl]aniline. The corresponding polyanilines, PClPA‐HA, PClPA‐SA, PClPA‐NA and PClPA‐PA, were characterized by means of ¹H NMR, ¹³C NMR, high resolution mass spectroscopy, Fourier transform infrared spectroscopy, ultraviolet–visible spectroscopy and SEM images. The elemental analysis and electrical conductivity of the polymers are also presented. It is shown that the molecular weight of the polymers obtained depends on the method of synthesis. Spectroscopic studies confirmed the emeraldine form of the polyaniline derivatives. In the work, the dependence of the current passing through resistive structures based on thin poly[2‐(2‐chloro‐1‐methylbut‐2‐en‐1‐yl)aniline] films on the relative humidity of air was studied. The results of the studies showed the prospects of using thin polymer films in the design of chemical sensors. © 2020 Society of Chemical Industry