Abstract In this study 3-chloro-2-hydroxypropyltrimethylammonium chloride was used as a cationic agent to cationize cotton fabric by a pad-batch process.

The cationized cotton samples were dyed with different reactive dyes containing various reactive groups. The dyeability of the cationized cotton samples with reactive dyes without salt was significantly improved due to an increase in the ionic attraction between the dye and cationized cotton. The results showed that the wash and dry rubbing fastness of the cationized cotton dyed with different reactive dyes are similar to those of the untreated cotton. However, the light fastness of some of the cationized fabric samples was improved. Keywords Salt - Reactive dye - Cotton - Cationization - Fastness - Pretreatment Fulltext Preview

Preparation of cationic cotton with two-bath pad-bake process and its application in salt-free dyeing Lili Wang, Wei Ma , , Shufen Zhang, Xiaoxu Teng, Jinzong Yang State Key Laboratory of Fine Chemicals, Dalian University of Technology, No. 158 Zhongshan Road, Dalian 116012, PR China Received 26 December 2008. Revised 11 April 2009. Accepted 28 May 2009. Available online 8 June 2009. http://dx.doi.org/10.1016/j.carbpol.2009.05.022, How to Cite or Link Using DOI Cited by in Scopus (4) Permissions & Reprints View full text

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Abstract Cationic cotton was prepared by a designed two-bath pad-bake process with 3-chloro-2-hydroxypropyltrimethylammonium chloride as cationizing reagent to realize recycle utilization of the reagent and continuous processing of cationization. Experiments showed that 8.0% (o.w.bath) of the reagent, 1:1 of molar ratio of sodium hydroxide to the reagent, 60 C and 6 min of baking temperature and time were selected for cationization and the obtained cationic cotton was suitable for application in salt-free reactive dyeing. The structures of both the untreated and cationic fibers were investigated by X-ray diffraction and scanning electronic microscopy. Higher dye utilization and color yields could be realized on the cationic cotton than that on the untreated one in the conventional dyeing. Levelness dyeing and good fastness properties of the dyes on the cationic fabrics were obtained. Besides,

colorimetric properties and mechanical strength of the dyed fabrics were both evaluated to show applicability of this preparation process of cationic cotton. Keywords

Cationic cotton; Two-bath pad-bake process; Salt-free dyeing; Reactive dyes

Figures and tables from this article:

Fig. 1. Structures of the reactive dyes used in this study. View Within Article

Fig. 2. Effect of CHPTAC concentration (a), molar ratio of sodium hydroxide to CHPTAC (b), baking temperature (c) and time (d) on F% of C.I. Reactive Blue 19 on cationic cotton. View Within Article

Fig. 3. X-ray diffraction patterns of untreated cotton fiber (a) and cationic cotton fiber (b). View Within Article

Fig. 4. SEM photos of untreated cotton fiber (a and b) and cationic cotton fiber (c and d). View Within Article

Fig. 5. Comparison of F% of 5 reactive dyes on cationic and untreated cotton. View Within Article

Scheme 1. Reactions occurred during the cationization process of cotton. View Within Article Table 1. Fastness properties of the reactive dyes and mechanical strength of the dyed cotton. View Within Article Table 2. Colorimetric data for the dyed cotton with different reactive dyes. View Within Article Corresponding author. Tel.: +86 411 82945527. Copyright 2009 Elsevier Ltd. All rights reserved. Color variations of anthraquinone and azo re... Dyes and Pigments The identification of the derivatives of C.I... Water Research The removal of reactive dye printing compoun... Dyes and Pigments

Electrochemically assisted photocatalytic de... Applied Catalysis B: Environmental Adsorption of the selected organic dyes on t... Dyes and Pigments View more related articles Related reference work articles e.g. encyclopedias 9.12 - Metal Complexes as Speciality Dyes an... Comprehensive Coordination Chemistry II More related reference work articles

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Download this Document for Free Claims:What is claimed is:1. A compound of the formula: wherein: R 1 ,R 2 , and R 3 each are independently selected from the group consisting of C 1 to C 20 alkyl C 5 -C 12 cycloalkyl, and C 6 -C 10 aryl, each of which is optionally substituted by 1-3 amino, hydroxyl, C 1 -C 4 alkoxy orC 1 -C 4

alkyl; or R 1 and R 2 , together with N, form a 5, 6 or 7 membered heterocyclic ring or a 5, 6, or 7membered heterocyclic aromatic ring, optionally substituted by one or more hydroxyl, amino, amide,carboxyl, carbonyl, or C 1 -C 4 alkyl; or R 1 ,R 2 , and R 3 , together with N, form a bridged heterocyclic ring,optionally substituted by one or more hydroxyl, amino, amide, carboxyl, carbonyl or C 1 -C 4 alkyl; R 4 ishydrogen or C 1 -C 4 alkyl; X is C 1 -C 10 alkylene substituted by 1 to 3 hydroxyl; R 5 is a triazinyl ring having atleast one halogen substituent; Y is NH, NR 4 , O, or S; Z is C 6 -C 10 arylene, C 5 -C 12 cycloalkylene, or C

2 -C 10 alkylene; and An () is an anion.2. The compound of claim 1, wherein each R 1 ,R 2 , and R 3 is C 1 to C 4 alkyl; and R 4 is hydrogen.3. The compound of claim 1, wherein X is wherein X 1 is C 1 -C 8 alkylene. 4. The compound of claim 1, wherein each Y is NH and Z is a benzene ring.5. A compound of the formula:6. A process for making a quaternary amine compound, comprising the steps of condensing an amine of the formula wherein: R 1 ,R 2 , and R 3 each are independently selected from the group consisting of C 1 -C 20 alkyl, C 5 -C 12 cycloalkyl,and C 6

-C 10 aryl, each of which is optionally substituted by 1-3 amino, hydroxyl, C 1 -C 4 alkoxy or C 1 -C 4 alkyl;or R 1 and R 2 , together with N, from a 5, 6 or 7 membered heterocyclic ring or a 5, 6, or 7 memberedheterocyclic aromatic ring, optionally substituted by one or more hydroxyl, amino, amide, carboxyl,carbonyl, or C 1 -C 4 alkyl; or R 1 ,R 2 , and R 3 , together with N, form a bridged heterocyclic ring, optionallysubstituted by one or more hydroxyl, amino, amide, carboxyl, carbonyl, or C 1 -C 4 alkyl; R 4 is hydrogen orC 1 -C 4 alkyl; X is C 1 -C 10 alkylene substituted by 1 to 3 hydroxyl groups, with a triazinyl ring substituted by at least three halogen substituents, wherein one of saidhalogen substituents reacts with said amine

to provide a reactive heterocyclic quaternary amineof the formulawherein R 1 ,R 2 ,R 3 ,R 4 , and X are as defined above, and R 5 is the residue of said triazinyl ringand having at least two halogen substituents; and coupling two molecules of said reactive heterocyclic quaternary amine with a bridging compoundselected from the group consisting of C 6 -C 10 aryl, C 5 -C 12 cycloalkyl, and C 2 -C 10 alkyl and substituted with atleast two groups selected from the group consisting of OH, SH, NH 2 , and NR 4 H to couple twomolecules of said reactive heterocyclic quaternary amine of formula (III) via reaction with said halogensubstituents of R 5 , to form a quaternary amine compound of the formula wherein R 1 ,R 2 ,R 3 ,R 4 , X, and R 5 are as defined above, Y is NH, NR

4 , O, or S; and Z is C 6 -C 10 arylene, C 5 -C 12 cycloalkylene, or C 2 -C 10 alkylene. 7. The process of claim 6, wherein: each R 1 ,R 2 and R 3 is C 1 -C 4 alkyl, R 4 is hydrogen, and X is wherein X 1 is C 1 -C 8 alkylene; and the two molecules of said reactive heterocyclic quaternary amine are reacted with benzene substitutedwith two groups selected from the group consisting of SH, NH 2 , or NR 4 H.8. The process of claim 7, wherein said amine is 1-amino-2-hydroxy3-trimethylammonium propanechloride (AHTAPC), said triazinyl ring substituted by at least three halogen substituents is cyanuricchloride, and said substituted benzene is p-phenylene diamine.9. The process of claim 6, wherein: said condensing step is conducted at a pH of about 4 to about 8 anda temperature of about 0

to about 15 C.; and said coupling step is conducted at a pH of about 4 toabout 8 and a temperature of about 30 to about 50 C.10. The process of claim 9, wherein: said condensing step is conducted at a temperature of about 0 toabout 5 C. and a pH of about 6.5; and said coupling step is conducted at a temperature of about 35 toabout 40 C., and pH of about 6.5.11. The process of claim 8, further comprising prior to said condensing step the step of reacting 2-3epoxy propyl Ntrimethylammonium chloride with ammonia to form 1-amino-2hydroxy-3-trimethylammonium propane chloride. Description: FIELD OF THE INVENTION This invention relates to compounds and processes for using the same to improve the dyeabilityof textile fibers and fibrous assemblies. More particularly, the present invention relates toquaternary ammonium compounds and processes for using the same to dye cellulosic fibers andfibrous assemblies with anionic dyes without the use of salt. BACKGR OUND OF THE INVENTION Many dyestuffs are rendered water-soluble by the incorporation of anionic groups into the dyemolecule. However, the surface of cellulosic substrates is also negatively charged, and thus tendsto repel anionic dyestuffs. Therefore, prior to the instant invention, virtually all dyes classified asanionic required some level of salt to speed the dyeing process.Specifically, in a typical anionic dyeing process, the dye and the cellulosic substrate (cotton,rayon, etc.) are placed into a hot water bath, in which the cellulosic substrate swells. Salt is thenadded to the water to salt the dye out of solution and into the fiber. Indeed, conventionalanionic dyeing processes for cellulosic fibers can employ significant amounts of salt, such assodium chloride or sodium sulfate, as a dyebath exhausting agent. However, use of salts indyeing can result in environmental problems relating to disposal of the exhausted dyebath.Fiber reactive quaternary ammonium compounds have been used in conjunction with anionicdyes to increase various dyeing characteristics (such as color, color fastness, and the like). Saltfree dyeing of cellulosic substrates has also been reported. For example, U.S. Pat. Nos. 5,330,541and 5,489,313, both to Hall et al., report the use of a quaternary ammonium pretreat to eliminatesalt in anionic dyeing of cellulose. In particular, the Hall et al.patents are directed to the use of anepoxy propyl trimethyl ammonium chloride pretreatment to eliminate salt in dyeing.While these and other compounds can be useful in the dyeing of cellulosic fibrous assemblies,commercial use of such compounds has been limited. Such compounds can lack sufficientsubstantivity for the cellulose to provide subsequent dye color yield values comparable to thoseachieved when dyeing in the presence of salt. In addition, such processes can exhibit limitedadaptability to

various dye processes, and in particular to exhaustion or long liquor processesusing conventional liquor ratios. In addition, it can be difficult to uniformly apply thesecompounds and/or control increased dyestuff rate-of-strike. Still further, these reagents can reactsluggishly so that fixation of the compounds to a fabric must be conducted under relativelydrastic conditions, for example, at elevated temperatures, high pH, and/or lengthy reaction times. S UMM ARY OF THE INVENTION The present invention provides processes for dyeing textile fibrous assemblies having notableecological advantages over conventional dyeing processes requiring the addition of salt to thedye-bath. Specifically, the present invention provides processes for improving the dyeability of textile fibrous assemblies containing cellulosic fibers without requiring a salt to drive thedyestuff into the cellulosic fiber. As a result, the expense, handling difficulties and disposalproblems associated with salt can be eliminated. In addition, the dyes can exhaust completely tothe fibrous assemblies and provide desirable deeper shades, thus maximizing dye utilization andallowing significant reductions in dyestuff usage. Further, the resulting textiles can be uniformlydyed and possess good colorfastness, thereby eliminating or minimizing the need for a fixative.Still further, the processes of the invention can be used with a variety of dyeing techniques, suchas pad batch and exhaustion processes. Indeed, in contrast to prior salt-free dyeing techniques,the present invention allows the use of conventional liquor ratios in an exhaustion process. Thusthe processes of the invention can also provide significant advantages in efficiency and cost ascompared to conventional dyeing processes.In the invention, fibrous assemblies comprising cellulosic fibers are treated with an aqueouscomposition comprising a novel highly substantive fiber reactive cationic compound of theformula (I) below:wherein:R 1 ,R 2 , and R 3 each are independently selected from the group consisting of C 1 to C 20 alkyl, C 5 -C

12 cycloalkyl, and C 6 -C 10 aryl, each of which is optionally substituted by 1-3 halogen,amino, hydroxyl, C 1 -C 4 alkoxy or C 1 -C 4 alkyl; or R 1 and R 2 , together with N, form a 5, 6 or 7 membered heterocyclic ring, such as pyrrolidine, pyrrolidone, piperidine, morpholine,piperazine and the like, or form a 5, 6, or 7 membered heterocyclic aromatic ring such aspyridine, pyrrole, pyrimidine, imidazole, nicotinamide and the like, wherein each of saidheterocyclic ring or heterocyclic aromatic ring may be optionally substituted by one or morehydroxyl, amine, amide, carboxyl, carbonyl or C 1 -C 4 alkyl; or R 1 ,R 2 , and R 3 , together withN, form a bridged heterocyclic ring, such as quinuclidine, 1,4-diazabicyclo[2.2.2]octane(DABCO), and the like, optionally substituted by one or more hydroxyl, amine, amide, carboxyl,carbonyl or C 1 -C 4 alkyl;R 4 is hydrogen or C 1 -C

4 alkyl;X is C 1 -C 10 alkylene, preferably substituted by hydroxyl;R 5 is a 5 or 6 membered heterocyclic aromatic ring, preferably containing one or more nitrogenatoms, and having at least one reactive substituent capable of bonding with hydroxyl and aminegroups;Y is NH, NR 4 or S;Z is C 6 -C 10 aryl, C 5 -C 12 cycloalkyl, or C 2 -C 10 alkylene; and An () is an anion.Preferably, each R 1 ,R 2 , and R 3 is C 1 to C 4 alkyl; R 4 is hydrogen; X is of the formula:wherein X 1 is C 1 -C 10

-alkylene; R 5 is a triazine ring substituted with at least one halogen; eachY is NH or NCH 3 ; and Z is benzene. In an especially preferred embodiment of theinvention, the compound has the formulaThe cellulosic substrate is also treated with a suitable alkaline agent, such as sodium carbonate,under conditions sufficient to allow the pretreatment compound to covalently react with thecellulosic fibers of the fabric. The cationic reactant and alkaline agent can be applied to thefabric simultaneously or sequentially.The fabric can then be dyed using a variety of anionic dyes, such as fiber reactive dyes, directdyes, sulfur dyes, and vat dyes, using various dyeing techniques. Because the compounds of theinvention can exhibit pronounced reactivity with hydroxyl groups of the cellulosic fibers, thecompounds of the present invention can be applied under mild conditions. Accordingly, theprocess can be carried out at lower temperatures, lower pH values, and/or shorter reaction timesthan that required for prior fixing agents, such as those noted above which include an epoxygroup as the reactive radical. In addition, such pretreated fibrous assemblies can be dyed usingan exhaustion process with conventional process conditions. Further, the dyestuffs aresubstantially fully exhausted onto the fibrous assembly, resulting in a dyed material having good,uniform color and colorfastness. The remaining dye-bath effluent is substantially colorless(water-white) and free from undesirable salts, contaminants and the like.Compounds of Formula (I) above are also provided in another aspect of the invention. Thecompounds of the invention can exhibit improved substantivity for cellulosic fibers as comparedto traditional quaternary amines, in particular low molecular weight quaternary amines such asepoxy propyl trimethyl ammonium chloride. Due to its high substantivity, the compound can beapplied to the cellulosic fibers under so-called long-liquor conditions, and the treated cellulosicfibers can subsequently be dyed with, for example, reactive dyes having water solubilizinggroups such as sulphonate groups, without salt additions to the dyebath. In addition, thecompounds allow use of a wider range of commercial process equipment to pretreat the fiber,while maintaining superior results. Thus, conventional dyeing procedures, equipment androutings can be used. In particular, the results achieved with the compound of the instantinvention are superior to those previously possible with the use of conventional quaternaryamines applied from conventional longliquor exhaustion dyeing processes.The present invention also provides cellulosic fibrous assemblies having a fiber reactive cationiccompound of Formula (I) bound to the hydroxyl sites of the cellulosic fibers thereof, andprocesses for making the compounds of the invention.

DET A ILED DE S CR IPTION OF THE P R EFE RR ED EM B ODIMENT S The present invention will be described more fully hereinafter in connection with illustrativeembodiments of the invention which are given so that the present disclosure will be thorough andcomplete and will fully convey the scope of the invention to those skilled in the art. However, itis to be understood that this invention may be embodied in many different forms and should notbe construed as being limited to the specific embodiments described and illustrated herein.Although specific terms are used in the following description, these terms are merely for purposes of illustration and are not intended to define or limit the scope of the invention.The fiber reactive cationic compounds of the invention have at least two fiber reactive sites and,in a preferred embodiment, also have at least two dye reactive sites. The compounds have theformulawherein:R 1 ,R 2 , and R 3 each are independently selected from the group consisting of C 1 to C 20 alkyl, C 5 -C 12 cycloalkyl, and C 6 -C 10

aryl, each of which is optionally substituted by 1-3 halogen,amino, hydroxyl, C 1 -C 4 alkoxy or C 1 -C 4 alkyl; or R 1 and R 2 , together with N, form a 5, 6 or 7 membered heterocyclic ring such as pyrrolidine, pyrrolidone, piperidine, morpholine,piperazine and the like, or form a 5, 6, or 7 membered heterocyclic aromatic ring such aspyridine, pyrrole, pyrimidine, imidazole, or nicotinamide, and the like, all of which may beoptionally substituted by one or more hydroxyl, amine, amide, carboxyl, carbonyl, or C 1 -C 4 alkyl; or R 1 ,R 2 , and R 3 , together with N, form a bridged heterocyclic ring, such asquinuclidine, 1,4-diazabicyclo[2.2.2]octane (DABCO), and the like, optionally substituted byone or more hydroxyl, amine, amide, carboxyl, carbonyl or C 1 -C 4 alkyl;X is C 1 -C 10 alkylene, preferably substituted by hydroxyl;R 5 is a 5 or 6 membered heterocyclic aromatic ring, preferably containing one or more nitrogenatoms, and having at least one reactive substituent capable of bonding with hydroxyl and aminegroups;Y is NH, NR 4

 or S;Z is C 6 -C 10 aryl, C 5 -C 12 cycloalkyl, or C 2 -C 10 alkylene; andAn () is an anion.Preferably, each R 1 ,R 2 , and R 3 is C 1 to C 4 alkyl; R 4 is hydrogen or C 1 -C 4 alkyl; X iswherein X is C 1 -C 10 -alkylene, preferably methylene; R 5 is a 6 membered heteroaryl selectedfrom the group consisting of pyridine, pyrimidine, quinoxaline and triazine, preferably triazine,substituted with halogen; each Y is NH or NCH 3 ; and Z is benzene. Exemplary anionsinclude anions of both organic and inorganic acids, and include without limitation chloride, salt free dyeing Download this Document for FreePrintMobileCollectionsReport Document Info and Rating

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