Abstract:
Fibrous materials are dyed or printed by treatment with an aqueous preparation containing (a) 1 : 2-chromium or 1 : 2-cobalt complexes of azo or azomethine dyestuffs which contain at least one -SO3H or -COOH group imparting solubility in water and do not form covalent bonds with the fibrous material or with aminoplants and (b) water-soluble or at least dispersible aminoplants and curing the treated material in the presence of an acidic catalyst. The fibrous materials may be leather or paper or fibres of glass, cellulose acetate, polyamide, polyurethane, polyacrylonitrile, polyester or especially cellulose fibres such as viscose rayon and cotton. The metal complexes (a) may be formed from 1 atom of metal and two molecules of the same dyectuff, one molecule each of two different dyestuffs or one molecule of dyestuff and one molecule of a colourless complex former. The dyes may contain one or more azo linkages or azomethine groups and the 1 : 2-metal complex preferably contains 2-4 -SO3H groups. The dyestuffs while containing no reactive groups (including acid amide groups) may be substituted with, for example, methyl, methoxy, ethoxy groups, aromatically bound hydroxyl groups or chlorine atoms. Specified complex-forming groups are o, o1-dihydroxyazomethine, o-carboxymethoxy-o1-hydroxyazo, o-carboxy-o1-hydroxyazo, o-carboxy-o1-aminoazo, o-hydroxy-o1-aminoaza and preferably, o, o1-dihydroxyazo groupings. The preferred dyestuffs have one azo linkage and may be prepared in the usual way by diazotising o-carboxy-amines or o-hydroxyamines of benzene or naphthalene and coupling with aminonaphthalenes, hydroxybenzenes, hydroxynaphthalenes, 2 : 4-dihydroxyquinolines, pyrazolones or barbituric acid capable of coupling vicinal to an amino, hydroxyl or enolisable keto group. Many aminoplants (b) are specified but those preferred are methylolureas and methylolmelamines which may be etherified with lower alcohols, e.g., methanol. The aqueous preparations may also contain a latex of a polymerization plastic especially polymers of ethylenically unsaturated monomers or water-insoluble aminoplants. A polyethylene emulsion is employed in the examples as a softener and many others are specified. Specified acidic catalysts are ammonium sulphate and chloride, diammonium phosphate, ethanolamine hydrochloride, zinc nitrate, zinc fluoborate and ammonium silicofluoride. The aqueous preparations may also contain wetting or dispersing agents, usual thickeners and hydrotropic agents. The preparations are preferably applied in a continuous manner e.g. by padding at 10-40 DEG C. or by roller printing. Curing may be effected at 120-180 DEG C. preferably with previous drying at below 100 DEG C. except in the case of viscose rayon where the impregnated material may be left in the moist state for 1-6 hours before dyeing and curing. According to the content of the aqueous preparations additional effects of crease and shrink resistance, permanent calender, water repellency and modified handle may be obtained simultaneously. The cured dyeings and prints may be soaped and rinsed. Examples of dyeing and printing cotton and viscose fabrics are given.
Abstract:
The present invention is directed to dye mixtures comprising structures of formula and their production and their use for dyeing textiles and in particular for dyeing aramid fibres.
Abstract:
1:2-metal complex dyes of the formula wherein the symbols R1, R1′, R2, R2′, R3, R3′, Y, Z, n, n′, Me, M and (Kat)+ are defined as in the Claims, mixtures thereof, their compositions, their production and their use as anionic dyes for dyeing substrates, especially leather, in brown to red shades.
Abstract:
Compounds of the formula ##STR1## iron complexes thereof and mixtures of such iron complexes, wherein D is a monocyclic or bicyclic aromatic diazo component radical of the benzene series containing one --SO.sub.3 M group or is ##STR2## R.sub.1 is hydrogen, methyl or ethyl, and R.sub.4 is hydrogen, chloro or C.sub.1-2 alkyl,wherein R' is hydrogen, C.sub.1-4 alkyl, C.sub.2-4 hydroxyalkyl, methoxy(C.sub.2-4 alkyl) or ##STR3## R" is hydrogen, C.sub.1-4 alkyl, C.sub.2-4 hydroxyalkyl or methoxy(C.sub.2-4 alkyl), or--NR'R" is a saturated 5- or 6-membered ring,R.sub.5 is hydrogen, chloro or C.sub.1-2 alkyl, andX is hydrogen or hydroxy,wherein each R.sub.2 is independently hydrogen, chloro, hydroxy, C.sub.1-2 alkyl, C.sub.1-2 alkoxy or --SO.sub.2 NR.sub.o R.sub.o, andeach R.sub.3 is independently hydrogen, C.sub.1-2 alkyl, C.sub.1-2 alkoxy, --COOM, trifluoromethyl or --NR"'R"",wherein each R"' and R"" is independently C.sub.1-4 alkyl, C.sub.2-4 hydroxyalkyl, methoxy(C.sub.2-4 alkyl) or carbamoyl(C.sub.1-2 alkyl), or--NR"'R"" is saturated 5- or 6-membered ring,each R.sub.o is independently hydrogen, C.sub.1-4 alkyl, C.sub.2-4 hydroxyalkyl or methoxy-(C.sub.2-4 alkyl), or--NR.sub.o R.sub.o is a saturated 5- or 6-membered ring, andeach M is independently hydrogen or a cation,which iron complexes and mixtures of iron complexes are useful for dyeing substrates dyeable with anionic dyes such as leather.
Abstract:
Dye mixtures which comprise at least one anionic acid dye of the formula ##STR1## together with at least one anionic acid dye of the formula ##STR2## in which the substituents are as defined in claim 1, and the novel dyes of the formulae (1) and (2) are direct dyes for cellulosic fibre materials in particular. They have a high heat stability and are particularly suitable for one-bath, one-stage dyeing of polyester/cotton blend fabrics with a disperse dye for the polyester fibres under the dyeing conditions for polyester fibres.
Abstract:
1:2 chromium complex dyestuffs of the formula (I) ##STR1## in which A, B, R.sup.1, R.sup.2, R.sup.3, R.sup.4, p, m, n, n' and Cat.sup.(+) have the meaning given in the description, are suitable for dyeing and printing amido-containing materials.
Abstract:
1:2 metal complexes of the formula ##STR1## wherein each of R.sub.1 and R.sub.3 is independently hydrogen or nitro, with the proviso that when a ring has two nitro groups, they are meta to each other,each of R.sub.2 and R.sub.4 is independently hydrogen, chloro or --SO.sub.3 M,each of R.sub.5 and R.sub.6 is independently hydrogen, --COR.sub.7, --CONHR.sub.8 or --SO.sub.2 R.sub.9,wherein R.sub.7 is C.sub.1-6 alkyl, C.sub.1-6 alkoxy, phenyl(C.sub.1-4 -alkyl) or phenyl(C.sub.1-4 -alkyl) the phenyl group of which is substituted by 1 or 2 substituents selected from halo, C.sub.1-4 -alkyl, C.sub.1-4 alkoxy, nitro, amino, --COOM, --SO.sub.3 M and acetamido,R.sub.8 is hydrogen, C.sub.1-6 alkyl; phenyl; phenyl substituted by 1 or 2 substituents selected from halo, C.sub.1-4 -alkyl, C.sub.1-4 alkoxy, nitro, amino, --COOM, --SO.sub.3 M and acetamido; naphthyl or naphthyl monosubstituted by chloro, amino, phenylamino, acetamido, benzamido or --SO.sub.3 M, andR.sub.9 is C.sub.1-6 alkyl, phenyl or phenyl substituted by 1 or 2 substituents selected from halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, nitro, amino, --COOM, --SO.sub.3 M and acetamido, andMe is chromium or cobalt,wherein each M and M.sup..sym. is independently hydrogen or a non-chromophoric cation, with the provisos that (1) when both R.sub.5 and R.sub.6 are hydrogen, both R.sub.1 and R.sub.3 are hydrogen and at least one of R.sub.2 and R.sub.4 is chloro, and (2) the --NHR.sub.5 group is in the 2- or 3-position of Ring A and the --NHR.sub.6 group is in the 2- or 3-position of Ring B, and mixtures thereof, useful as dyes for dyeing or printing various materials, such as natural and synthetic polyamides and particularly for dyeing artificially produced oxide layers on and aluminum alloys.
Abstract:
A metal complex suitable as dyes for the dyeing of a wide range of textile and non-textile materials, particularly leather and fur, said metal complex of a compound of the formula ##STR1## in which D and D.sub.1, independently of one another, are each the radical of a diazo component of the benzene or naphthalene series and M is a phenylene radical which may be further substituted.
Abstract:
Dyes suitable for dyeing wool, polyamide and leather in orange, brown or olive-brown shades are disclosed, the dyes having the formula ##STR1## wherein A and D are each independently of the other a benzene or napththalene radical of a diazo component, which component carries the hydroxyl or carboxyl group in the ortho-position to the azo group;B is the radical of a coupling component which carries the group X adjacent to the azo group;X is oxygen or a radical of the formula --R--, in which R is hydrogen or C.sub.1 -C.sub.4 alkyl;Y is a radical of the formula ##STR2## in which formulae R.sup.1 and R.sup.5 are each independently of the other hydrogen or sulfo, R.sup.4 is hydrogen or nitro, R.sup.6 is hydrogen, methyl, methoxy or chlorine and R.sup.2 and R.sup.3 are each independently of the other hydrogen, halogen, nitro or sulfo;Ar.sup.1 is a benzene or napththalene radical which is unsubstituted or substituted by halogen, nitro, sulfo, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy;m is 0 or 1;n is an integer from 1 to 7; andKa.sup..sym. is a cation.
Abstract:
Metal-free compounds of the formula ##STR1## 1:1 and 1:2 metal complexes thereof, and acid addition salts of metal-free compounds of said formula and 1:1 and 1:2 metal complexes thereof, whereinB is hydrogen; C.sub.1-4 alkyl; C.sub.1-4 alkyl monosubstituted by C.sub.1-4 alkoxy; C.sub.2-4 alkyl substituted by hydroxy; C.sub.5-6 cycloalkyl; C.sub.5-6 cycloalkyl substituted by 1 to 3 C.sub.1-4 alkyl groups; phenyl(C.sub.1-3 alkyl); phenyl(C.sub.1-3 alkyl) the phenyl group of which is substituted by 1 to 3 substituents selected from C.sub.1-4 alkyl, C.sub.1-4 alkoxy and halo; --A--NH--R.sub.2 ; --A'.sub.4 --N(R.sub.7).sub.2 ; --A.sub.4 --N.sup..sym. (R.sub.8).sub.2 R.sub.9 A.sup..crclbar. or --N(R.sub.7).sub.2,R is hydrogen; C.sub.1-4 alkyl; C.sub.5-6 cycloalkyl; C.sub.5-6 cycloalkyl substituted by 1 or 2 C.sub.1-4 alkyl groups; phenyl; phenyl substituted by 1 or 2 substituents selected from methyl, ethyl, methoxy and ethoxy; benzyl; phenylethyl; or benzyl or phenylethyl the phenyl group of which is substituted by 1 or 2 substituents selected from methyl, ethyl, methoxy and ethoxy,R.sub.1 is hydrogen or --N.dbd.N--D, wherein D is a diazo component radical, with the proviso that R.sub.1 must be ##STR2## when B is other than --A--NH--R.sub.2, andT is hydrogen, cyano, --COOR.sub.4, --CO--N(R.sub.5)2, --SO.sub.2 --N(R.sub.5).sub.2, ##STR3## with the provisos that (i) when the compound is a monoazo compound free of sulfo groups, it contains at least one water-solubilizing basic or cationic group, (ii) when the compound is free of sulfo groups and is other than a monoazo compound, it contains at least two water-solubilizing groups, and (iii) when the compound contains one or more sulfo groups, the total number of basic and cationic groups exceeds the number of sulfo groups by at least one,are useful as dyes except for the compounds wherein R.sub.1 is hydrogen which are useful as intermediates.