The present invention relates to a process for the trichromatic dyeing or printing hydroxy-group-containing or nitrogen-containing organic substrates with dye mixtures and also to such dye mixtures and hydroxy-group-containing or nitrogen-containing organic substrates dyed or printed therewith.
Trichromatic describes the additive colour mixing of suitable yellow- or orange-, red- and blue-dyeing dyes with which any desired shade in the visible spectrum can be obtained by suitably selecting the amount ratios for the dyes.
Trichromatic dyeing is well known from the literature for various dye classes, for example from EP 83299, DE 2623178, EP 226982 and EP808940.
Optimum trichromatic performance of any yellow (or orange), red and blue dye mixture is crucially dependent on the neutral affinity and migration characteristics. Dyes having identical or very similar characteristics with regard to neutral affinity and migration are highly compatible with regard to trichromatic performance.
It is an object of the present invention to provide a trichromatic dyeing process and associated trichromatic dye mixtures consisting of at least one red component, at least one yellow (or orange) component and at least one blue component whereby trichromatic dyeing with good fastnesses is obtained.
This object is achieved by a trichromatic dyeing process which is characterized by using a dye mixture comprising at least one red-dyeing compound of the formula (I)
wherein
Various auxiliaries, such as surface-active compounds, solubilising agents, thickeners, gel-forming substances, antioxidants, penetration agents, sequestering agents, buffers, light protection agents, care agents may additionally be present in the composition according to the invention.
Such auxiliaries are in particular wetting agents, antifoams, levelling agents, thickeners and plasticizers.
For the preparation of inks for printing processes suitable organic solvents or mixtures thereof are used. E.g. alcohols, ethers, esters, nitriles, carbonacidamides, cyclic amides, urea, sulfones and sulfone oxides.
Furthermore additional auxiliaries such as e.g. compounds, which adjust the viscosity and/or the surface tension, may be added to the ink composition.
Suitable yellow (or orange)-dyeing compounds for the inventive trichromatic process have the following formula (II)
wherein
wherein
wherein R8 C1-4alkyl; —NH2 or —NHC1-4alkyl,
and the asterisk marks the bond to the —N═N— group.
Further suitable yellow (or orange)-dyeing compounds for the inventive trichromatic process have the following formula (111)
wherein
wherein
Further suitable yellow (or orange)-dyeing compounds for the inventive trichromatic process have the following formula (IV)
wherein
wherein
Suitable blue-dyeing compounds for the inventive trichromatic process have the following formula (V)
wherein
wherein
wherein
Further suitable blue-dyeing compounds for the inventive trichromatic process have the following formula (VI)
in which
Further suitable blue-dyeing compounds for the inventive trichromatic process have the following formula (VII)
in which
Further suitable blue-dyeing compounds for the inventive trichromatic process have the following formula (VIII)
wherein
A preferred trichromatic dyeing process is characterized by using a dye mixture comprising at least one red-dyeing compound of the formula (Ia)
wherein
A more preferred trichromatic dyeing process is characterized by using a dye mixture comprising at least one yellow (or orange)-dyeing compound of formula (IIa), (IIb) and/or (IIc)
wherein A is
and/or at least one yellow (or orange)-dyeing compounds of formula (IIIa) or (IIIb)
wherein D is
and/or at least one yellow (or orange)-dyeing compounds of formula (IVa) or (IVb)
wherein RG is
A more preferred trichromatic dyeing process is characterized by using a dye mixture comprising and/or at least one blue-dyeing compound of formula (Va), (Vb), (Vc), (Vd), (Ve) and/or (Vf)
wherein T is
and/or at least one blue-dyeing compounds of formula (VIa) or (VIb)
and/or at least one blue-dyeing compounds of formula (VIIa) or (VIIb)
and/or at least one blue-dyeing compound of formula (VIIIa)
It is to be noted that all compounds may also be present in salt form. Useful salts include in particular alkali metal, alkaline earth metal or ammonium salts or the salts of an organic amine.
It is likewise to be noted that the alkyl groups can be linear or branched.
Preferred hydroxy-group-containing or nitrogen-containing organic substrates are leather and fibrous materials, which comprise natural or synthetic polyamides and, particularly, natural or regenerated cellulose such as, cotton, viscose and spun rayon. The most preferred substrates are textile materials comprising cotton.
Compounds of the formula (I) are prepared by reacting a diazotized compound of the formula (1)
wherein all substituents have the meanings as defined above,
with a compound of the formula (2)
wherein all substituents have the meanings as defined above.
The process is preferably carried out in an aqueous medium at a temperature of from 0 to 40° C., more preferably 0 to 25° C. and at a pH of between 1 to 7, more preferably 1 to 6.
A dyestuff of formula (I) may be isolated in accordance with known methods, for example by salting out, filtering and drying optionally in vacuum and at slightly elevated temperature.
The yellow (or orange)-dyeing compounds are known from the state of the art and can therefore be produced according to the process given in the prior art. E.g. WO9963995, WO9963055 and F.Lehr, Dyes Pigm. (1990), 14(4), 257.
The blue-dyeing compounds are also known from the state of the art and can therefore be produced according to the process given in the prior art. E.g. EP 99721, EP84314, WO0168775, EP 149170, EP497174 and DE4241918.
This invention further provides dye mixtures for the trichromatic dyeing or printing of hydroxy-group-containing or nitrogen-containing organic substrates are used in the above processes according to the invention.
The inventive process for trichromatic dyeing or printing can be applied to all customary and known dyeing and printing processes, for example the continuous process, the exhaust process, the foam dyeing process and the ink-jet process.
The composition of the individual dye components in the trichromatic dye mixture used in the process according to the invention depends on the desired hue. For instance, a brown hue preferably utilizes 30-65% by weight of the yellow (or orange) component according to the invention, 10-30% by weight of the red component according to the invention and 10-30% by weight of the blue component according to the invention.
The red component, as described above, can consist of a single component or of a mixture of different red individual components.
The same applies to the yellow (or orange) and blue components.
The total amount of dyes in the process according to the invention is between 0.01 and 15% by weight, preferably between 1 and 10% by weight.
The present invention further provides hydroxy-group-containing or nitrogen-containing organic substrates dyed or printed by a dye mixture according to the invention.
The process according to the invention provides dyeings and prints having a homogeneous hue build-up throughout the entire hue spectrum with on-tone exhaustion, with a high bath exhaustion even in the case of fibres with low saturation and with a high dye build-up on fine fibres, particularly on microfibres.
The resulting dyeings or prints are notable for very high wet fastnesses, specifically the fastnesses in washing, perspiration and water. These good wet and fabrication fastnesses, which are in no way inferior to the fastness level of dyeings and prints with metal complexes, are obtained without aftertreatment. With an additional aftertreatment these fastnesses are even exceeded.
These excellent results are provided by metal-free elements which meet the current and future ecological requirements of national institutes and regulations.
The tables which follow show some examples of the individual components of the dye mixtures which are used in the inventive trichromatic dyeing process.
(5)-
(5)-
(5)-
(5)-
(5)-
(5)-
(5)-
The application examples hereinbelow serve to illustrate the present invention. Parts are by weight and temperatures are in degrees Celsius, unless otherwise indicated.
A 20 g sample of bleached cotton knitting. is transferred in a solution of 16 g sodium sulfate in 200 ml water at 60° C.,
These examples are made analogous to Use Example 1, but by using dyestuff mixtures as mentioned below. The resulted shade is given in brackets.
Number | Date | Country | Kind |
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0124842.6 | Oct 2001 | GB | national |
Filing Document | Filing Date | Country | Kind | 371c Date |
---|---|---|---|---|
PCT/IB02/04216 | 10/14/2002 | WO | 00 | 4/16/2004 |
Publishing Document | Publishing Date | Country | Kind |
---|---|---|---|
WO03/033600 | 4/24/2003 | WO | A |
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20040250358 A1 | Dec 2004 | US |