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Dyes with two monochlorotriazine or with two monochlorotriazine and two vinylsulphone reactive groups have been investigated for establishing an enhancement of the dyeability of cotton fabrics. The effect of the diamine bridge linking two chromophore systems on the degree of dye exhaustion from the dyebath and dye bonding with the cellulose fibre was examined. The excellent water solubility of these dyes make them useful in the exhaustion method of dyeing. The kind of diamine used as a bridging group has a significant influence on exhaustion and fixation values. The application of diamine, which assures the chemically linear structure of the dye, affects the increase in the amount of the dye fixed on the fibres. Apart from the derivatives of ethylene-1,2-diamine and phenylene-1,2-diamine, the remaining dyes are characterised by a very high degree of dye exhaustion from the dyebath. The dyes examined can be successfully used for dyeing cellulose fibres by the exhaustion process. 2003
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AUTEX Research Journal, Vol. 3, No2, June 2003 © AUTEX
http://www.autexrj.org/No2-2003/0055.pdf
NOVEL REACTIVE RED DYES
Edyta Matyjas, Edward Rybicki
Technical University of Lodz
Department of Textile Finishing
Zeromskiego 116, 90-534 Lodz, Poland
Abstract
Dyes with two monochlorotriazine or with two monochlorotriazine and two vinylsulphone
reactive groups have been investigated for establishing an enhancement of the dyeability
of cotton fabrics. The effect of the diamine bridge linking two chromophore systems
on the degree of dye exhaustion from the dyebath and dye bonding with the cellulose
fibre was examined. The excellent water solubility of these dyes make them useful in the
exhaustion method of dyeing. The kind of diamine used as a bridging group has a
significant influence on exhaustion and fixation values. The application of diamine, which
assures the chemically linear structure of the dye, affects the increase in the amount of
the dye fixed on the fibres. Apart from the derivatives of ethylene-1,2-diamine and
phenylene-1,2-diamine, the remaining dyes are characterised by a very high degree of
dye exhaustion from the dyebath. The dyes examined can be successfully used for
dyeing cellulose fibres by the exhaustion process.
Keywords
fibre-reactive dyes, bi-functional reactive dyes, bridging group, cellulosics fabrics, dyeing,
exhaustion, fixation
Introduction
Commercially reactive dyes were used for the first time over [[35 years ago]]. Their structure is
attributed to chemical bonding between suitable groups in the dye molecule and hydroxyl groups in
the cellulose fibre. Before the introduction of reactive dyes, cotton was often dyed with direct, vat,
sulphur and azoic dyes. For about four decades before the use of reactive dyes, these dyes remained
the only feasible method of achieving dyeings of high fastness to wash cellulose textiles.
The characteristic structural features of a typical reactive dyes molecule are:
the reactive system, enabling the dyes to form covalent bonds between the dye and the
substrate,
the chromophoric grouping, contributing to the colour and much to the substantivity for
cellulose,
a bridging group that links the reactive system to the chromophore, and
solubilising groups.
The reactive grouping is attached directly to the chromophore, and most reactive systems contain a
heterocyclic ring which contributes to substantivity for cellulose. The nature of the bridging group and
other substituents on the heterocyclic ring greatly influences the reactivity and other dyeing
characteristics of reactive dyes. Many reagents can be used as a reactive system, but only a few have
met the requirements to become commercially established in a significant segment of the market.
The chlorotrazinyl and vinylsulphone groups have been firmly established as the main reactive system
for cellulose.
Dye manufacturers have for a long time recognised the need to improve the fixation levels of reactive
dyes. As a result some of the reactive dyes with more than one reactive group in the dye molecule
have been investigated. Reactive systems are often classified according to the number of reactive
groups contained in the dye molecule, as mono-, bi- and poly-functional reactive systems.
Experimental
We examined the three series of bi-functional reactive dyes based on 1-amine-8-hydroxynephthalene-
3,6-disulphonic acid, with either a monochlorotriazine reactive system or with monochlorotriazine and
91
vinylsulphone groups lying on the opposite site of the dye chromophore, linked by a diamine unit and
disposed between the triazine rings.
The structure of the obtained dyes is shown by the general formula:
Dw
N
N
NNH
N
OH
NA
SO3Na
NaO3S
Cl
N
N
N
NH
N
OH
N
A
NaO3SSO3Na
Cl
Figure 1. The general formula of reactive dyes
where: A – the active component;
A-1 orthanilic acid
A-2 anthranilic acid
A-3 4-(β-ethylsulphate)sulphonylaniline
Dw – diamines;
Dw-1 phenylene-1,2-diamine
Dw-2 phenylene-1,3-diamine
Dw-3 phenylene-1,4-diamine
Dw-4 diaminestilbene-2,2'-disulphonic acid
Dw-5 4,4'-diaminebenzoanilide
Dw-6 ethylene-1,2-diamine
The dyes were subjected to spectrophotometric analysis and assessment of the λmax
in an acetone-water 2:1 solution and a 25% pyridine solution by means of a Spekol 11
spectrophotometer, made by Carl-Zeiss Jena, Germany. The dye concentration in solution was 25
mg/dm3.The content of the salt in the dyes was determined by potentiometric titration. The structure of
the dyes and the results of spectrophotometric measurements are listed in Table 1:
Table 1. Dyes structures, dye content and spectrophotometric properties of dyes
dye structure λmax, nm
dye diazo component diamine dye content, % acetone:water (2:1) 25% pyridine
R-1 A-1 Dw-1 72.3 542 540
R-2 A-1 Dw-2 56.1 542 540
R-3 A-1 Dw-3 58.0 542 540
R-4 A-1 Dw-4 62.1 542 540
R-5 A-1 Dw-5 36.7 542 540
R-6 A-2 Dw-1 34.0 520 550
R-7 A-2 Dw-2 38.3 550 550
R-8 A-2 Dw-3 31.9 550 550
R-9 A-2 Dw-4 54.5 550 550
R-10 A-2 Dw-5 43.4 550 550
R-11 A-2 Dw-6 47.5 550 550
R-12 A-3 Dw-1 33.9 520 520
R-13 A-3 Dw-2 34.4 518 521
R-14 A-3 Dw-3 36.1 522 524
R-15 A-3 Dw-4 44.1 520 524
R-16 A-3 Dw-5 40.6 522 522
R-17 A-3 Dw-6 29.9 518 522
92
Dye application
Bleached cotton fabric was used in the dyeing experiments after washing in an aqueous solution
of 2 ml/dm3 non-ionic detergent (Precolor Jet). The fabrics were rinsed several times in water and
dried at room temperature. The fabric samples were dyed in a BFA-12 Mathis Labomat laboratory
dyeing machine manufactured and granted us by Warner Mathis AG Textile Machines, Switzerland, in
a dyebath containing 1% (o.w.f.) dye and a 10:1 liquor ratio. The dyebath contained 40 g of NaCI and
10 g of Na2CO3 per 1 dm3 of the dyebath. All fabrics were wetted out in cold water before the dyeing
process was carrying out. The dyed samples were dried at room temperature. The temperature course
of the dyeing process is shown in Figure 2.
Figure 2. Temperature course of the dyeing process
Determination of dye exhaustion and fixation
The extent of exhaustion achieved for a 1% dyeing on cotton fibres was determined using
spectroscopic analysis of the dye bath before and after dyeing at different times. The calibration curve
for each dye was determined by measuring the absorbance of the dye solution of known
concentrations. The changes in absorbance versus concentration for each dye in an acetone:water
2:1 solution, as well as in 25% pyridine solution. were plotted.
The percentage of dyebath exhaustion achieved for each dye was calculated from the following
formula:
%
c
cc
E100
1
21
= (1)
where: E- the degree of dye exhaustion from the dyebath, in percent,
1
c, 2
c - the concentration of the dye before and after dyeing, respectively.
The absorbed but unfixed dye on the cellulose fibres was removed by repeated extraction
with a 25% pyridine solution. Next, the fabric was rinsed in water and dried at room temperature.
This allowed us to determine the degree of dye fixed on the fibre. The dye fixation ratio was estimated
using two methods:
the difference between the quantity of dye in fibre and that dissolved in the pyridine solution was
used to determine the degree of dye fixation ratio. The percentage dye fixation ratio for each dye
was calculated from the following formula:
%
c
c
T100
2
1= (2)
93
where: T- the fixation ratio determined by method 1, in percent,
1
c, 2
c - the concentration of the dye after and before extraction respectively.
the reflectance values of each dyed sample were measured before and after extraction in a
pyridine solution with a Macbet Colour Eye 3000 spectrophotometer, a product of a division of the
Kollmorgen Corporation, Newburgh, USA. The percentage dye fixation ratio for each dye was
calculated using the following formula:
()
()
%
S/K
S/K
TS/K 100
2
1= (3)
where: TKIS - the fixation ratio determined by method 2, in percent,
()
1
/SK ,
()
2
/SK - the colour strength values of dyed samples after and before extraction
respectively.
From the result of the dye exhaustion and fixation ratio, the fixation yield was calculated for all dyeings
by the given formula:
%
ET
F
100
= (4)
where: F - the fixation yield, in percent,
E, T - the degrees of dye exhaustion and dye fixation ratio respectively, in percent.
Primary exhaustion - the percentage of the dye absorbed onto the fibre before the addition of sodium
carbonate, relative to the amount of the dye used for experiment;
Secondary exhaustion - the percentage of the dye absorbed or chemically bound to the fibre
at the end of the dyeing process but before extraction with pyridine solution, relative to the amount of
the dye used for experiment;
Fixation ratio - the percentage of the dye chemically bound to cellulose at the end of the dyeing
process, relative to secondary exhaustion;
Fixation yield - the percentage of dye chemically bound to cellulose at the end of the dyeing process,
relative to the amount of dye used for the experiment.
The results of dye exhaustion and fixation values were shown in Table 2.
Table 2. Degrees of dye exhaustion from the dyebath and the dye fixation ratio and the fixation yield
Degree of exhaustion, % Fixation ratio, % Dye
Primary
exhaustion, %
Secondary
exhaustion, %
Method I Method II
Fixation yield, %
R-1 21.9 41.3 83.8 77.4 34.6
R-2 53.9 86.9 64.2 73.4 55.4
R-3 76.2 86.3 63.9 68.9 55.1
R-4 53.9 78.9 81.6 82.1 70.9
R-5 32.5 60.1 76.4 76.6 67.5
R-6 44.3 50.9 59.8 52.6 30.3
R-7 87.9 94.9 76.8 76.9 72.8
R-8 79.0 91.5 91.8 92.2 77.6
R-9 79.6 84.5 64.3 69.7 54.3
R-10 67.5 72.3 97.0 64.8 48.4
R-11 60.6 64.4 58.1 87.2 37.4
R-12 39.5 72.3 94.8 94.6 68.5
R-13 53.2 81.4 94.6 95.8 76.9
R-14 34.7 66.2 90.4 91.8 59.9
R-15 41.3 66.9 95.4 97.2 63.8
R-16 35.6 54.4 92.3 91.3 50.2
R-17 21.7 44.6 89.4 86.5 39.9
where:
for dyes delivered from orthanilic acid for dyes delivered from 4-(β-ethylsulphate)sulphonylaniline
for dyes delivered from anthranilic acid
94
Figure 3 shows the plot of primary and secondary exhaustion degree from the dyebath. The plot
of the fixation values of the dyes is shown in Figure 4.
Figure 3. Plot of the primary and secondary exhaustion degree from dyebath
Figure 4. Plot of fixation ratio and fixation yield
Results and Discussion
The derivatives of 1-amine-8-hydroxynaphtalene-3,6-disulphonic acid are red dyes which showed high
water solubility due to the presence of many sulphonic groups (from 6 to 8) and their symmetric
arrangement in the dye molecule. Their excellent solubility in water makes it possible to carry out the
application process with the low liquor ratio of 1:10 using 40 g of NaCI per 1 dm3 of the dyebath. With
95
an increased molecule size of the dyes examined, an increasing substantivity to cellulose fibres was
observed.
The kind of active compound used in chromophoric grouping has a great influence on exhaustion and
fixation values. The bi-functional reactive dyes (the derivatives of anthranilic acid (R-6 - R-11)) show
the highest secondary exhaustion degree from the dyebath. As expected, the derivatives
of 4-(β-ethylsulphate)sulphonylaniline dyes showed the lowest secondary exhaustion degree values
due to the presence of vinylsulphone reactive groups in the dye molecule. Despite the low exhaustion
from the dyebath, these dyes (R-12 to R-17) showed the highest
fixation ratio, starting from 89% for derivative of ethylene-1,3-diamine to 95% for derivative
of diaminestilbene-2,2'-disulphonic acid.
The kind of diamines used as bridging groups influences the dyeing characteristics of the dyes
examined. Among the derivatives of phenylenediamine, the highest degree of exhaustion and fixation
values were shown by the derivatives of phelylene-1,3-diamine. The derivatives
of ethylene-1,2-diamine showed the lowest degree of exhaustion and fixation values, which can be
explained by spherical hindering or changes in reactivity. Application of those amines that ensure the
linear chemical structure of the dye molecule causes an increase in the degree of exhaustion and
fixation values.
The results obtained show that the kind of diamine used as a bridging group and the kind of active
compound affect the degree of exhaustion and consequently the degree of dye fixed
on cellulose fibres.
Acknowledgements
The authors would like to express their gratitude to Dr. K Blus of the Department of Dyes,
Technical University of Lodz, for synthesis of the reactive red dyes used in this work.
References
[1] J. Shore, Cellulosics Dyeing, ‘CHAPTER 4: Dyeing with reactive dyes’, Society of Dyers
and Colourists, Manchester 1995.
[2] BASF Aktiengesellschaft, US Patent 6180765 B1, January 2001.
[3] Dystar Textilfarben GmbH & Co., US Patent 6090163, July 2000.
[4] BASF Aktiengesellschaft, US Patent 6359121 B1, March 2002.
[5] Everlight USA Inc., US Patent 6068667, May 2000.
[6] BASF Aktiengesellschaft, US Patent 6159250, December 2000.
[7] E. Matyjas, E. Rybicki, Application of the bi-functional reactive dyes in periodical method
of dyeing. (Zastosowanie dwufunkcyjnych barwników reaktywnych w okresowych sposobach
barwienia), IV Scientific Conference of the Faculty of Textiles (IV Konferencja Naukowa Wydziału
Włókienniczego), Lodz 2001.
[8] A Łukoś , W. Ornaf, Reactive Dyes (Barwniki reaktywne), WPL Warsaw 1966.
[9] W. Czajkowski, Reactive dyes for cellulose fibres. (Barwniki reaktywne do włókien
celulozowych), XVIII Training Seminar of Colourists (XVIII Seminarium Szkoleniowe Kolorystów),
Szczyrk 2002.
[10] J. Kraska , B. Łandwijt, The Influence of chemical structure of the chromophoric grouping
and diamines on the properties of the triazine reactive dyes. (Wpływ budowy chemicznej
układu barwnego i dwuamin nawłaściwości dwureaktywnych barwników triazynowych),
Textile Review (Przegląd Włókienniczy), (1979); 33: No.9, 507-510.
[11] J. Mielicki, On the conformity of dyes. (O zgodności barwników), XVIII Training Seminar
of Colourists (XV Seminarium Szkoleniowe Kolorystów)., Szczyrk 2002.
[12] J. Mielicki, Outline of Colour Knowledge. (Zarys wiadomości o barwie), Foundation
of Development of Polish Colourists (Fundacja Rozwoju Polskich Kolorystów) 1997.
... Matyjas i Rybicki su ispitivali primenu diamina, kao mosta za povezivanje, na iscrpljenje i fi ksiranje bifunkcionalnih reaktivnih boja na pamuku [8]. Utvrdili su da primena diamina, koja osigurava hemijski linearnu strukturu boja, utiče na poveć anje količine iscrpljene i fi ksirane bifunkcionalne boje sa monohlortriazinskom i vinil sulfonskom grupom. ...
... U pogledu razlike u tonu uzorci oznake R2 su više žuti (+DH * ), a uzorci oznake R3 su više plavi (-DH * ). Kao u predhodnom slučaju ukupna razlika u boji DE * je velika (7,(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)8) i u slučaju bojenja u realnom sistemu zamena jedne boje drugom zahteva dopunske korekcije. U tabeli 7 prikazane su razlike u obojenju za seriju uzoraka obojnih reaktivnim plavim bojama. ...
... U pogledu razlike u tonu uzorci oznake R2 su više žuti (+DH * ), a uzorci oznake R3 su više plavi (-DH * ). Kao u predhodnom slučaju ukupna razlika u boji DE * je velika (7,(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)8) i u slučaju bojenja u realnom sistemu zamena jedne boje drugom zahteva dopunske korekcije. U tabeli 7 prikazane su razlike u obojenju za seriju uzoraka obojnih reaktivnim plavim bojama. ...
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Dyeing with reactive dyes', Society of Dyers and Colourists
  • J Shore
  • Cellulosics Dyeing
J. Shore, Cellulosics Dyeing, 'CHAPTER 4: Dyeing with reactive dyes', Society of Dyers and Colourists, Manchester 1995.
The Influence of chemical structure of the chromophoric grouping and diamines on the properties of the triazine reactive dyes
  • J Kraska
  • B Łandwijt
J. Kraska, B. Łandwijt, The Influence of chemical structure of the chromophoric grouping and diamines on the properties of the triazine reactive dyes. (Wpływ budowy chemicznej układu barwnego i dwuamin nawłaściwości dwureaktywnych barwników triazynowych), Textile Review (Przegląd Włókienniczy), (1979); 33: No.9, 507-510.
On the conformity of dyes. (O zgodności barwników), XVIII Training Seminar of Colourists (XV Seminarium Szkoleniowe Kolorystów)
  • J Mielicki
J. Mielicki, On the conformity of dyes. (O zgodności barwników), XVIII Training Seminar of Colourists (XV Seminarium Szkoleniowe Kolorystów)., Szczyrk 2002.
Reactive Dyes (Barwniki reaktywne), WPL Warsaw
  • A Łukoś
  • W Ornaf
A Łukoś, W. Ornaf, Reactive Dyes (Barwniki reaktywne), WPL Warsaw 1966.
Outline of Colour Knowledge. (Zarys wiadomości o barwie), Foundation of Development of Polish Colourists
  • J Mielicki
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