Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Reexamination Certificate
2000-10-02
2002-02-26
Powers, Fiona T. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
C534S605000, C534S612000, C008S428000, C008S436000, C008S437000, C008S549000, C008S917000, C008S918000, C008S919000, C008S924000
Reexamination Certificate
active
06350862
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-fiber 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 fibers such as polyamides.
Examples of classes of such reactive dyes which are well known in the art include dyes containing a mono- or dichloro- or fluoro- 1,3,5-triazinyl group, mono- or dichloro or fluoro-pyrimidyl group, beta-halogen-propionyl group, beta-halogenoethyl-sulphonyl group, beta-halogenoethylsulphamyl group, chloroacetyl amino, beta-(chloro-methyl)-beta-sulphatoethylsulphamyl group, or a vinyl sulphonyl group.
In the case of the dyes containing a triazinyl group or a pyrimidyl group, in place of the reactive halogen atoms one can use other groups which dissociate in the presence of alkali. Canadian Patent 771632, for example, discloses examples of such other groups including sulphonic acid, thiocyanate, sulphophenoxy, sulphophenyl thio, nitrosulphophenoxy groups, and quaternary ammonium groups.
Dyes and Pigments 14, 1990, pages 239-263, “Synthesis and Application of Reactive Dyes with Heterocyclic Reactive Systems” discloses fiber reactive dyes containing monochloro- or dichloro- pyrimidine heterocycle with quaternary ammonium substituents.
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-fiber covalent Fixation Value (F). The Fixation Value (F) of a dye compound is a measure of the dye affinity at the substrate surface or in other words the percentage of dye removed from the substrate by the so-called post-dyeing “soaping off process”, based on the dye originally absorbed during the dyeing process. Thus there if 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 fiber reactive dye compounds comprising a monofluoropyrimidine heterocycle or a monochloromonofluoro pyrimidine heterocycle substituted with at least one quaternized nitrogen derivative such as nicotinate, exhibit significantly increased values of Exhaustion (E) and Fixation (F), particularly on cellulosic substrates such as cotton, and show significant improvements in terms of reducing 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 fiber reactive dyes. In addition, the compounds of the present invention provide significantly more intense dyeings, and can be used for both high and low temperature dyeing. Furthermore, the compounds of the present invention can be used together with specific chromophores for cotton dyeing using significantly reduced levels of salt needed for dyeing.
SUMMARY OF THE INVENTION
According to the present invention there is provided a reactive dye compound having the formula (I):
wherein:
D is a chromophore group;
L is a linking moiety;
Q is a quaternized nitrogen derivative;
X and Y are independently selected from chlorine, bromine, fluorine or hydrogen;
A is selected from halogen, preferably chlorine or fluorine;
provided that at least one of X and Y is fluorine and salts and esters thereof
The compounds of the present invention exhibit increased Exhaustion (E) and Fixation (F) values and provide improvements in terms of reducing spent dyestuff in effluent, increasing dye affinity to the substrate, 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.
DETAILED DESCRIPTION OF THE INVENTION
As used herein the term “reactive dye” means a dye containing a one or more reactive groups, that is to say one or more groups capable of forming covalent bonds with the substrate to be dyed, or a dye which forms such a group in situ.
As used herein the term “Exhaustion” in relation to fiber reactive dyes means the percentage of dye which is transferred from a solution of the dye to the substrate to be treated at the end of the dyeing process, before rinsing and soaping. Thus 100% Exhaustion means that 100% of the dye is transferred from the dye solution to the substrate.
As used herein the term “Fixation” in relation to reactive dyes means the percentage of dye which covalently bonds with the substrate, based on the dye originally absorbed during the dyeing process. Thus 100% Fixation means that 100% of the dye absorbed is covalently bonded with the substrate.
Reactive dye compounds of the present invention may be represented by the following formula (I):
wherein:
D is a chromophore group;
L is a linking moiety;
X and Y are independently selected from chlorine, bromine, fluorine or H;
A is a halogen preferably chlorine or fluorine.
provided that at least one of X and Y is fluorine.
Chromophore Moiety
Any chromophore moieties suitable for use for dyeing substrates can be used in the present invention.
Any chromophore moieties suitable for use for dying substrates can be used in the present invention. The term chromophore as used herein means any photoactive compound and includes any colored or non-colored light absorbing species, eg. fluorescent brighteners, UV absorbers, IR absorbing dyes.
Suitable chromophore moieties for use in the dye compounds herein include the radicals of monoazo, disazo or polyazo dyes or of heavy metal complex azo dye derived therefrom or of an anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthene, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye.
Suitable chromophore moieties for use in the dye compounds herein include those disclosed in EP-A-0,735,107 (Ciba-Geigy), incorporated herein by reference, including the radicals described therein which contain substituents customary for organic dyes, such as sulphonate substituents which enhance the water-soluble properties of the dye compound
Most preferred chromophore D groups for use herein are polysulphonated azo chromophores such as those present Drimalan (RTM) dyes commercially available from Clariant and Drimarene (RTM) dyes commercially available from Clariant.
Linking Moiety
The compounds herein further comprise a linking moiety to link the pyrirnidine heterocycle to the chromophore moiety. Any linking moieties suitable for
Brock Earl David
Lewis David Malcolm
Yousaf Taher Iqbal
Murphy Stephen T.
Peebles Brent M.
Powers Fiona T.
The Procter & Gamble & Company
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