Reactive dye compounds

Details Reactive dye compounds Reactive dye compounds

2002-03-27

2004-09-14

Powers, Fiona T. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Azo

C534S638000, C534S642000, C540S133000, C544S189000, C544S211000, C552S232000, C008S428000, C008S524000, C008S528000, C008S543000, C008S549000

Reexamination Certificate

active

06790943

ABSTRACT:

TECHNICAL FIELD
The present invention relates to reactive dye compounds. In particular the present invention relates to reactive dye compounds having improved dye-bath Exhaustion (E) and improved dye-fibre covalent Fixation (F).
BACKGROUND OF THE INVENTION
Reactive dye compounds are known in the art for dyeing various substrates. Such substrates include for example proteinaceous materials such as keratin, e.g. found in hair, skin and nails and various animal body parts such as horns, hooves and feathers, and other naturally occurring protein containing materials, e.g. silk and saccharide-derived materials such as those derived from. cellulose or cellulose derivatives, e.g. natural products such as cotton, and synthetic fibres such as polyamides.
Examples of classes of such reactive dyes which are well known in the art include dyes containing a vinyl sulphone group or vinyl sulphone precursor groups such as those commercially available from Dystar under the tradename Remazol.
There are many different types of commercially-available reactive dyes for dyeing cellulosic and polyamide-type substrates. However, a critical problem still facing the textile dye industry today is the significant level of dyestuff material which remains in the effluent waste water after the dyeing process is finished. The industry measure for this problem is known as dye-bath Exhaustion (E). A high Exhaustion value for a particular dye compound means that a low level of spent dye remains in the effluent after the dyeing process is complete, while a low Exhaustion value means that a high level of spent dye remains in the effluent. There is clearly a need therefore for new dye compounds which have higher Exhaustion Values compared with commercially available dye compounds, and which provide benefits in terms of reducing levels of spent dyestuff in effluent water.
As well as having a high Exhaustion Value, it is also important for a dye compound to have a high dye-fibre covalent Fixation Value (F). The Fixation Value (F) of a reactive dye compound is a measure of the extent of covalent bonding with the substrate based on the dye originally absorbed during the dyeing process. Thus 100% Fixation means that 100% of the absorbed dye covalently bonds to the substrate. Thus, there is clearly a need to provide dye compounds having increased Fixation Values. A high Fixation Value can result in a simplification of the post dyeing “soaping off process” traditionally associated with fiber reactive dye compounds. In particular, a high Fixation Value can result in a reduced time spent on the “soaping off process” together with a reduced cost.
It has now been surprisingly found that a new class of fibre reactive dye compounds derived from vinyl sulphone dyes and their precursors such as chloroethylsulphone, sulphatoethylsulphone, phosphoethylsulphone, and other blocked ethyl sulphones as known. in the art, comprising at least one chromophore group, at least one SO
2
C
2
H
4
group and at least one substituent derived from a hydrated aldehyde, a hydrated ketone, a hydrated alpha-hydroxyketone or the hydrated form of formic acid, linked via one of its oxygen atoms to the terminal carbon atom of the SO
2
C
2
H
4
group and hence forming a hemiacetal, such as for example the hydrated form of sucrose or glucose, and the hydrated form of formic acid, exhibit significantly increased values of Exhaustion (E) and Fixation (F). These dyes can be used on a wide variety of substrates. They are particularly useful for cellulosic substrates, such as cotton and/or cotton blends, and show significant improvements in terms of decreasing the amount of spent dyestuff in effluent, increasing dye affinity to the substrate, increasing the efficiency of the dye-substrate covalent reaction, and simplifying the post dyeing “soaping off process” traditionally associated with reactive dyes. In addition, the compounds of the present invention provide significantly more intense dyeings not achievable with current reactive dyes, and can be used for both high and low temperature dyeing, hence reducing the cost of the dyeing process. Furthermore, the compounds of the present invention can be used together with specific chromophores for cellulose substrate dyeing leading to significantly reduced levels of salt needed for dyeing.
SUMMARY OF THE INVENTION
According to the present invention there is provided a reactive dye compound comprising:
(a)at least one chromophoric moiety
(b)at least one SO
2
C
2
H
4
group which is attached to the chromophoric moiety either directly via the sulphur atom of the SO
2
C
2
H
4
group or via a linking group L;
characterised in that at least one SO
2
C
2
H
4
group is substituted on its terminal carbon atom with at least one Y group wherein Y is derived from a hydrated aldehyde, a hydrated ketone, a hydrated alpha-hydroxy ketone or the hydrated form of formic acid, and linked via one of its oxygen atoms to the terminal carbon of the SO
2
C
2
H
4
group thereby forming a hemiacetal.
The compounds of the present invention exhibit increased Exhaustion (E), Fixation (F) and Efficiency (T) values and provide improvements in terms of reducing spent dyestuff in effluent, increasing dye affinity to the substrate, increasing the efficiency of the dye-substrate covalent reaction, ability to carry out the long-liquor dyeing process at room temperature as well as at elevated temperatures, and simplifying the post dyeing “soaping off process” traditionally associated with fiber reactive dyes. In addition, the compounds of the present invention provide significantly more intense dyeings, i.e. greater colour intensity in the dyed substrate, without compromising levelness. Typical Exhaustion Values for the compounds and products herein are greater than 95%. Typical Fixation Values for the compounds and products herein are greater than 95%.


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