Back to results
US 5,541,299 AGranted
Process for the preparation of dyestuffs
AssigneeBayer Aktiengesellschaft
InventorsRoderich Raue, Alfred Brack, Karl-Heinrich Lange
Life of this patent
Estimating the term…
Abstract
Dyestuffs of the formula ##STR1## in which D is the radical of an aromatic or heterocyclic diazo component and K is the radical of an aromatic or heterocyclic coupling component, or is the radical of an active methylene compound, are obtained in an ecologically advantageous manner by reacting an aromatic or heterocyclic diazo components of the formula D--NH.sub.2 and a coupling component of the formula H--K with a nitrite, for example NaNO.sub.2, in the presence of CO.sub.2 at a pressure of 5-100 at. The process is suitable in particular for the preparation of concentrated dye-stuff solutions, because expensive operations, such as, for example, pressure permeation and reverse osmosis, can be omitted.
Claims15
A process for the preparation of a dyestuff of the general formula
- D--N.dbd.N--K (I)
- in which
- D is the radical of a substituted or unsubstituted aromatic diazo component containing 6 to 10 carbon atoms or is the radical of a heterocyclic diazo component selected from the group consisting of substituted and unsubstituted, benzo-fused and non-benzo-fused thiazoles, isothiazoles, thiadiazoles, oxazoles, imidazoles and triazoles and
- K is the radical of a substituted or unsubstituted aromatic coupling component containing 6 to 10 carbon atoms or
- K is the radical of a heterocyclic coupling component of the formula ##STR49## in which R.sup.12 represents methyl, phenyl, carboxamide or carboxylic alkyl esters of 1-4 C atoms, and
- R.sup.13 represents hydrogen, an amidino group or a phenyl radical which is unsubstituted or substituted by 1-3 halogens, alkyl, alkoxy, carboxyl, carboxamido, sulpho or sulphonamido groups,
- A represents hydroxyl or amino
- R.sup.14 represents hydrogen, alkyl of 1-4 C atoms or phenyl,
- R.sup.15 represents hydrogen, alkyl or 1-4 C atoms or a phenyl radical which is unsubstituted or substituted by 1-3 halogens, alkyl or alkoxy radicals of 1-4 C-atoms, and
- R.sup.16 represents halogen, alkyl or alkoxy of 1-4 C atoms,
- q is 0, 1 or 2,
- or
- HK is selected from the group consisting of 2-hydroxy-carbazole, 3-hydroxy-di-benzofurane, 5-hydroxyquinoline, 8-hydroxyquinoline, 5-hydroxyisoquinoline, 2,4-dihydroxyquinoline, 1-(m-nitrophenyl)-3-methyl-5-pyrazolone, 1-(p-nitrophenyl)-3-methyl-5-pyrazolone, 1,2,3,4-tetrahydro-6-methoxyquinoline, 1,2,3,4-tetrahydro-7-methylquinoline, 1,2,3,4-tetrahydro-1-methylquinoline, 1,2,3,4-tetrahydro- 1-(2-hydroxyethyl)quinoline, 3,4-dihydro-2H- 1,4-benzoxazine (benzomorpholine), 4-ethyl-3,4-dihydro-2H-1,4-benzoxazine, 4-(2-cyanoethyl)-3,4-dihydro-2H-1,4-benzoxazine, julolidine, 2-acetamido-thiophene, 2-benzamidothiophene, 2-dimethylaminothiazole;
- indazol-6-one, 1-dimethylaminomethyl-3-methylpyrazol-5-one,
- or
- HK is an activated methylene coupling component selected from the group consisting of .beta.-diketones, beta-keto esters, beta-keto nitriles, anilides of cyano-acetic acid, heterocyclic beta-keto amides and .beta.-imino amides or
- K is a radical of the formula ##STR50## in which R.sup.1 represents hydrogen or alkyl having 1-4 carbon atoms which is unsubstituted or substituted by halogen, hydroxyl, cyano, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylcarbonyloxy, phenoxy, phenyl, hydroxycarbonyl or C.sub.1 -C.sub.4 -alkylsulphonyl,
- R.sup.2 and R.sup.3, independently of one another, represent methyl or ethyl and
- R.sup.4 represents hydrogen, halogen, alkyl or alkoxy having 1-4 C atoms, benzyl, benzyloxy, phenyl or phenoxy radicals each of which in turn is unsubstituted or substituted by halogen, alkyl or alkoxy of 1-4 C atoms, acetyl benzoyl or carboxylic esters having 1-4 C atoms,
- m represents 1 or 2,
- and as far as substituents for the substituted aromatic diazo component, the substituted heterocyclic diazo component or the substituted aromatic coupling component, are concerned, they are selected from the group consisting C.sub.1 -C.sub.4 -alkyl, C.sub.6 -C.sub.10 -aryl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkylcarbonyloxy, cyano, C.sub.1 -C.sub.4 -(di)alkylamino, C.sub.1 -C.sub.4 -(di)alkylaminocarbonyl, C.sub.1 -C.sub.4 -alkylcarbonyl-amino, halogen, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkylsulphonyl, C.sub.1 -C.sub.4 -(di)alkylaminosulphonyl, C.sub.1 -C.sub.4 -alkylsulphonylamino, C.sub.1 -C.sub.4 -alkoxysulphonyl, C.sub.1 -C.sub.4 -alkylsulphonyloxy, nitro, C.sub.6 -C.sub.10 -(di)arylamino, C.sub.1 -C.sub.4 -alkyl-C.sub.6 -C.sub.10 -aryl-amino, phenylsulphonyl, phenylazo, benzothiazolyl, 1,2,4-oxadiazolyl, morpholino, piperidino, piperazino, pyrrolidino, C.sub.1 -C.sub.4 -alkylmercapto and C.sub.6 -C.sub.10 -arylmercapto,
- wherein substituents for the substituted aromatic diazo component or the substituted heterocyclic diazo component may optionally be hydroxy in which a diazo component of the formula
- D--NH.sub.2
- and a coupling component of the formula
- H--K
- are reacted in an aqueous medium with a nitrite selected from the group consisting of alkali nitrite, C.sub.1 -C.sub.5 -alkyl nitrite, glycol nitrite or polyol nitrite, at a CO.sub.2 pressure of more than 5 bar at a temperature of 0.degree.-125.degree. C.
23 more elements
A process for the preparation of the dyestuff of the formula ##STR51## in which R.sup.1 represents hydrogen or alkyl having 1.degree.-4 carbon atoms wherein said alkyl is unsubstituted or substituted by halogen, hydroxyl, cyano, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylcarbonyloxy, phenoxy, phenyl, hydroxycarbonyl or C.sub.1 -C.sub.4 -alkylsulphonyl,
- R.sup.2 and R.sup.3, independently of one another, represent methyl or ethyl,
- R.sup.4 and R.sup.5, independently of one another, represent hydrogen, halogen, alkyl or alkoxy having 1-4 C atoms, benzyl, benzyloxy, phenyl or phenoxy radicals wherein each of said benzyl, benzyloxy, phenyl or phenoxy radicals are unsubstituted or substituted by halogen, alkyl or alkoxy of 1-4 C atoms, acetyl, benzoyl or carboxylic ester having 1-4 C atoms or
- R.sup.5 represents phenylazo or together with the benzene ring form a tetraline, naphthalene or benzodioxane ring system and
- m and n, independently of one another, represent 1 or 2,
- is obtained by reacting an aromatic amine of the formula ##STR52## and a compound of the formula ##STR53## in which R.sup.1 to R.sup.5, m and n have the abovementioned meaning and
- R.sup.6 and R.sup.7, independently of one another, represent hydrogen, alkoxy of 1-4 C atoms, phenyl, phenoxy or C.sub.1 -C.sub.2 -alkyl with the proviso that R.sup.6 and R.sup.7 together do not contain more than 2 alkyl carbon atoms,
- are reacted in an aqueous medium with a nitrite selected from the group consisting of alkali nitrite, C.sub.1 -C.sub.5 -alkyl nitrite, glycol nitrite or polyol nitrite, in the presence of CO.sub.2 at a pressure of 5-100 bar at a temperature of 0.degree.-125.degree. C.
4 more elements
Dependencies are inferred from the claim text.