GB2031932A - Fibre-reactive azo dyestuffs - Google Patents
Fibre-reactive azo dyestuffs Download PDFInfo
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- GB2031932A GB2031932A GB7931489A GB7931489A GB2031932A GB 2031932 A GB2031932 A GB 2031932A GB 7931489 A GB7931489 A GB 7931489A GB 7931489 A GB7931489 A GB 7931489A GB 2031932 A GB2031932 A GB 2031932A
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- amino
- dyestuff
- alkyl
- general formula
- methylbenzene
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/085—Monoazo dyes
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- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Dyestuffs have the formula <IMAGE> in which the benzene ring or naphthalene ring A optionally contains further substituents, in addition to sulpho groups, R is H, alkyl (C1-4), R1 and R2 are H or optionally substituted alkyl or cycloalkyl, and R1 and R2 together with the nitrogen atom to which they are attached for a heterocyclic ring which may contain a further hetero-atom, R3 is H, alkyl (C1-4) or acylamino, R4 is H, alkyl (C1-4), alkoxy (C1-4), carboxyl or sulpho and n is 1, 2 or 3. These dyestuffs are suitable for dyeing and printing fibre materials containing hydroxyl groups or amide groups, in particular fibre materials of cotton.
Description
SPECIFICATION
Fibre-reactive azo dyestuffs
The invention relates to fibre-reactive azo dyestuffs of the formula
wherein
the benzene ring or naphthalene ring A can also contain further substituents, in addition to sulpho group,
R = hydrogen or C1-C4-alkyl,
R1 and R2 = hydrogen, optionally, substituted alkyl or cycloalkyl, or
R1 and F2 form a ring with the nitrogen atom, optionally with the inclusion of a further heteroatom,
R3 hydrogen, C1-C4-alkyl or acylamino,
n = 1,2 or 3, in particular optionally substituted C1-C4-alkylcarbonylamino or arylcarbonylamino, formylamino, oxalylamino or optionally substituted ureido, and
R4 = hydrogen, C1-C4-alkyl, C1-C4-alkoxy, carboxyl or sulpho.
Examples or substituents of the benzene ring or naphthalene ring A are the following: halogen atoms, such as fluorine, chlorine or bromine, C1-C4-alkyl, such as methyl, ethyl or n-propyl, C1-C4-alkoxy, such as methoxy, ethoxy, iso-propoxy or n-butoxy, acylamino, such as acetylamino, formylamino, oxalylamino, ureido, nitro, carboxyl and amino.
Examples of acylamino groups F3 are the following: acetylamino, ureido, hydroxyacetylamino, benzoylamino and the like.
Possible substituents for the alkyl radicals R1 and R2 are, in particular: hydroxyl, carboxyl, sulpho, optionally substituted phenyl or alkoxy, in particular C1-C4-alkoxy.
Examples of suitable optionally substituted alkyl radicals R1 and R2 are: Methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, t-butyl,- n-pentyl, n-hexyl, P-hydroxyethyl, p-methoxyethyl, ss-ethoxyethyl, carboxymethyl, t3-sulphoethyl, phenylmethyl, ss-phenylethyi and cyclohexyl.
Preferred alkyl radicals R1 and R2 are C1-C4-alkyl. Examples of cyclic compounds of the formula
are the following:
Dyestuffs of the formula
wherein
R, R1, R2, R3, R4 and n have the meaning indicated above;
wherein
R, R1, R2, R3 and R4 have the meaning indicated above and
m = 1 or 2;
wherein R1, R2 and n have the meaning indicated above and Rs acetylamino or ureido; and
wherein Ra, R2, R5 and m have the meaning indicated above, are preferred.
Quite generally, dyestuffs I-V in which R = H and R2 = H, alkyl or cycloalkyl and those in which R1 and R2 =
C2-C6-alkyl or together a ring optionally containing heteroatoms are preferred; those dyestuffs I-V in which R1 and R2 = H are very particularly preferred.
The invention furthermore relates to processes for the preparation of the dyestuffs (I). The following procedure may be mentioned in particular:
The dyestuff of the formula
wherein
R, F3, F4, A and n have the meaning indicated above, is subjected to a condensation reaction with 2,4,6-trifluoro-1 ,3,5-triazine, hydrofluoric acid being split off, and the resulting difluoro compound is reacted with an amine of the formula
hydrofluoric acid being split off, to give (I).
The condensation of the dyestuffs (VI) with s-trifluorotriazine is preferably carried out in aqueous solution or suspension, at low temperature and at a weakly acid, neutral to weakly alkaline pH value.
The condensation reaction is advantageously carried out in the pH range of 3-5. The hydrogen fluoride liberated is buffered by adding aqueous alkali metal hydroxides, carbonates or bicarbonates. The reaction of the difluoro compound with the amines (VII) is likewise preferably carried out in aqueous solution or suspension, at low temperature and at a neutral to weakly alkaline pH value. The hydrogen fluoride liberated during the condensation reaction is neutralised by adding aqueous alkali metal hydroxides, carbonates or bicarbonates. The neutralisation can advantageously also be carried out with a second equivalent of the amine (VII), in particular with ammonia. In general, isolation of the difluoro compound is dispensed with.
Examples of amines (VII) are the following: ammonia, methylamine, ethylamine, n-propylamine, iso-propylamine, n-butylamine, iso-butylamine, t-butylamine, n-pentylamine, n-hexylamine, cyclohexylamine, dimethylamine, diethylamine, di-n-propylamine, di-iso-propylamine, methylethylamine, ethanolamine, diethanolamine, ss-methoxyethylamine, ss-ethoxyethylamine, aminoacetic acid, N-methylaminoacetic acid, taurine, N-methyltaurine, benzylamine, ss-phenylethylamine, N-methylbenzylamine, pyrrolidine, piper- idine and morpholine.
The dyestuffs (i) can also be prepared by a process in which the dyestuffs (Vl) are reacted with an aminodifluorotriazine of the formula
wherein
R1 and R2 have the meaning indicated above, hydrofluoric acid being split off. This condensation reaction is preferably carried out in aqueous solution or suspension, at low temperature and at a weakly acid, neutral to weakly alkaline pH value. The hydrogen fluoride liberated during the condensation reaction is advantageously neutralised continuously by adding aqueous alkali metal hydroxides, carbonates or bicarbonates.
The following are mentioned as examples of difluorotriazine compounds.
2,4-DifI uoro-6-amino-1 ,3,5-triazine, 2,4-difl uo ro6-methylam ino-l ,3,5-triazi ne, 2,4-difluorn.-6- dimethylamino-1 ,3,S4riazine, 2,4-difl uoro-6-n-propylamino-1 ,3,S4riazine, 2,4-difluoro-6-ethylamino-1 ,3,5- triazine, 2,4-difluoro-6-diethylamino-1 ,3,5-triazine, 2,4-difluoro-6-n-butylamino-1 3,5-triazine, 2,4-difluoro-6 cyclohexylamino-1 ,3,S4riazine and 2,4-difluoro-6-morpholino-1 ,3,5-triazine.
The azo compounds of the formula (VI) used as starting substances for the preparation of the fibre-reactive azo dyestuffs of the formula (I) are obtained by diazotising aminobenzenesulphonic acids or aminonaphthalenesulphonic acids and coupling the diazotisation products to appropriate coupling components of the benzene series with a -NHR group.
The diazotisation is as a rule carried out by the action of nitrous acid in aqueous-mineral acid solution at low temperature, and the coupling is carried out at weakly acid, neutral to weakly alkaline pH values.
As diazo components and coupling components which can be used for the preparation of the azo compounds of the formula (I) there may be mentioned:
Diazo components: 1-aminobenzene-2-, -3- and -4-sulphonic acid, 1-aminobenzene-2,4- and -2,5disulphonic acid, 1-amino-4-methylbenzene-2-sulphonic acid, 1-amino-3-methylbenzene-6-sulphonic acid, 1-amino-6-methylbenzene-3- or -4-sulphonic acid, 1-amino-2,4-dimethylbenzene-6-sulphonic acid, 1-amino 4-or -5-chlorobenzene-2-sulphonic acid, 1-amino-6-chlorobenzene-3- or -4-sulphonic acid, 1-amino-3,4dichlorobenzene-6-sulphonic acid, 1-amino-2,5-dichlorobenzene-4-sulphonic acid, 1-amino-4methyl-5- chlorobenzene-2-sulphonic acid, 1-amino-5-methyl-4-chlorobenzene-2-sulphonic acid, 1-amino-4- or -5methoxybenzene-2-sulphonic acid, 1-amino-6-methoxy-benzene-3- or -4-sulphonic acid, 1-amino-6ethoxybenzene-3- or -4-sulphonic acid, 1-amino-2,4-dimethoxybenzene-6-sulphonic acid, 1-amino-2,5dimethoxybenzene-4-sulphonic acid, 1-amino-3-acetylaminobenzene-6-sulphonic acid, 1-amino-4acetylaminobenzene-2-sulphonic acid, 1 -amino-3-acetylamino-4-methylbenzene-6-sulphonic acid, 1-amino4-methoxybenzene-2,5-disulphonic acid, 1-amino-4-methyl-2,5-disulphonic acid, 1-amino-2- carboxybenzene-4- or -5-sulphonic acid, 1 -aminonaphthalene-2-, -4-, -5-, -6-, -7- or -8-sulphonic acid, 2-aminonaphthalene-1 -5- or -6-sulphonic acid, 1-aminonaphthalene-3,6- or -5,7-disulphonic acid, 2- aminonaphthalene-1 ,5-, -1,7-, -3,6-, -5,7-, -4,8- or -6,8-disulphonic acid, 1-aminonaphthalene-2,5,7trisulphonic acid and 2-aminonaphthalene-1 ,5,7-, -3,6,8- or-4,6,8-trisulphonic acid.
Coupling components: aminobenzene, N-methyl-, ethyl- or -butyl-aminobenzene, 1-amino-2- or -3methylbenzene, 1-methylamino-3-methylbenzene, 1-ethylamine-3-methylbenzene, 1 -amino-2,5- dimethylbenzene, 1-amino-2,5-diethylbenzene, -amino-2-ethoxybenzene, 1 -amino-3-acetylaminobenzene, 1 -amino-3-ureidobenzene, 1-amino-3-hydroxyacetylaminobenzene, 1-amino-3-sulphoacetylaminobenzene, 1-amino-3-methyl-6-methoxybenzene, 1-amino-3-acetylamino-6-methylbenzene, 1-amino-3-acetyl-amino-6- methoxybenzene, 1-amino-3-ureido-6-methylbenzene, 1-amino-2-methoxy-5-methylbenzene and 1-amino3-sulphatoacetylamino-benzene.
The new dyestuffs are suitable for dyeing and printing materials containing hydroxyl groups or amide groups, such as textile fibres-, filaments and fabrics of wool, silk and synethetic polyamide, and polyurethane fibres and for dyeing and printing natural or regenerated cellulose with dyeings and prints which are fast to washing, the treatment of cellulose materials appropriately being carried out, by the processes disclosed for reactive dyestuffs, in the presence of acid-binding agents and if appropriate by the action of heat.
The formulae indicated for the dyestuffs are those of the corresponding free acids. In general, the dyestuffs were isolated and employed for dyeing in the form of the alkali metal salts, in particular the Na salts.
Example 1
54.5 g of the dyestuff of the formula 3,6,8-trisulphonaphthalene < 2 azo 4 > 1 -amino-3-ureido-benzene are stirred in a mixture of 400 ml of water and 300 g of ice. 13.5 g of trifluorotriazine are added dropwise, the hydrofluoric acid liberated being buffered by 20% strength sodium carbonate solution at a rate such that the pH value is between 3 and 5. The resulting solution, in which starting material can no longer be detected, is adjusted to pH 9 with 12% strength ammonia solution, and ammonia is subsequently added dropwise at 0-10"C until the pH value remains constant. The dyestuff is salted out, filtered off, dried and ground. An orange dyestuff powder which dissolves readily in water giving a reddish-tinged yellow-coloured solution is obtained.The dyestuff corresponds to the formula
The dyestuff can also be isolated by evaporating or spray-drying the entire reaction mixture.
DYEING EXAMPLES
Printing instructions
When cotton nettle is printed with a printing paste which contains, per kilogram, 20 g of the dyestuff prepared according to Example 1), 100 g of urea, 300 ml of water, 500 g of alginate thickener (60 g of sodium alginate/kg of thickener) and 10 g of sodium carbonate and which was made up to 1 kg with water, and the cotton nettle is dried, steamed at 103'for 1 minute, rinsed with hot water and soaped at the boil, a reddish-tinged yellow print of good fastness to wet processing and light is obtained.
Padding instructions
30 parts of the dyestuff prepared according to Example 1) are dissolved in 1,000 parts of water. A cotton fabric is padded with this solution and pressed off to a weight decrease of 90%. The still moist cotton is treated for 30 minutes at 70"C in a bath which contains 300 parts of calcined sodium sulphate and 10 parts of calcined sodium carbonate, dissolved in 1,000 parts of water. The dyeing is then finished in the customary manner. A reddish-tinged yellow dyeing with outstanding fastness to wet processing and light is obtained.
Dyeing instructions
168 ml of water of 20-25"C are initially introduced into a dyeing beaker which has a capacity of 300 ml and is in a waterbath which can be heated. 0.3 g of the dyestuff obtained according to Example 1) is mixed thoroughly with 2 ml of cold water to form a paste and 30 ml of hot water (70"C) are added; the dyestuff thereby dissolves. The dyestuff solution is added to the initially introduced water and 10 g of cotton yarn is kept continuously in motion in this dye liquor. The temperature of the dye liquor is raised to 40-500C in the course of 10 minutes, 9 of anhydrous sodium sulphate are added and dyeing is continued for 30 minutes.
4 g of anhydrous sodium carbonate are then added to the dye liquor and dyeing is carried out at 40-50"C for 60 minutes. The dyed material is then taken out of the dye liquor, the adhering liquor is removed by wringing out or pressing off and the material is rinsed first with cold water and then with hot water until the rinsing liquor is not longer stained. The dyed material is then soaped at the boiling point for 20 minutes in 200 ml of a liquor which contains 0.2 g of a sodium alkyl-sulphate, rinsed again and dried at 60-700C in a drying cabinet. A reddish-tinged yellow dyeing of good fastness to washing and light is obtained.
If methylamine, dimethylamine, ethylamine, diethylamine, methylethylamine, iso-propylamine, nbutylamine, ethanolamine, diethanolamine, methylethanolamine, sulphuric acid mono-(2-aminoethyl ester), taurine, N-methyltaurine, aminoacetic acid, (2-aminoethyl) methyl ether, hexylamine, B-phenylethylamine, benzylamine or morpholine is used in Example 1) instead of ammonia, equally valuable dyestuffs with similar properties result.
If the procedure followed is according to the statement of Example 1), but instead of the aminoazo dyestuff used in that example equivalent amounts of the aminoazo dyestuffs listed in the table below are used and ammonia, methylamine, dimethylamine, ethylamine, diethylamine, methylethylamine, iso-propylamine,n-butylamine, ethanolamine, diethanolamine, methylethanolamine, sulphuric acid mono-(2-aminoethyl ester), taurine, N-methyltaurine, aminoacetic acid, (2-aminoethyl) methyl ether, hexylamine, ss- phenylthylamine, benzylamine or morpholine is used as the amine for replacing the second fluorine atom, equally valuable dyestuffs which dye cotton in yellow to reddish-tinged yellow shades result.
AMINOAZO COMPOUND FROM
No. Diazo component Coupling component 2 1-Aminonaphthalene-3,7- Aminobenzine
disulphonic acid 3 ,, 1 -Amino-3-methylbenzene 4 ,, 3-Aminophenylurea 5 ,, 1-Amino-3-hydroxyacetylamino-benzene 6 " 1-Amino-3-acetylamino-6-methoxy-benzene 7 " 1 ,, 1-Amino-3-acetylamino-6-methyl-benzene 8 " 1-Amino-3-acetylamino-benzene 9 " 1-Amino-3-methyl-6-methoxybenzene
10 " 1-Amino-3-ureido-6-methylbenzene 11 " N-Ethylaniline
12 " 1-Ethylamino-3-methylbenzene 13 " 1-Amino-2-methylbenzene
14 " 1 -Amino-2,5-dimethylbenzene 15 1-Aminonaphthatene-3,6- Aminobenzene
disulphonic acid 16 1 1-Amino-3-methylbenzene (Continued)
AMINOAZO COMPOUND FROM
No.Diazo component Coupling component 17 " 3-Aminophenylurea 18 1 -Am ino-3-hydroxyacetylamino-benzene 19 1 -Amino-3-acetylam ino-6-methoxy-benzene 20 1 -Amino-3-acetylamino-6-methyl-benzene 21 1 -Amino-3-acetylamino-benzene 22 " 1-Amino-3-methyl-6-methoxybenzene 23 " 1 -Amino-3-u reido-6-methylbenzene 24 N-Ethylaniline 25 " 1-Ethylamino-3-methylbenzene 26 " 1-Amino-2-methylbenzene 27 " 1 -Amino-2,5-dimethylbenzene 28 1-Aminonaphthalene-2,5,7- Aminobenzene
trisulphonic acid 29 " 1-Amino-3-methylbenzene 30 " 3-Aminophenylurea 31 1 -Amino-3-hydroxyacetylam lno-benzene 32 1 -Amino-3-acetyla mino-6-methoxy-benzene 33 ,, 1 -Amino-3-acetylam ino-6-methyl-benzene 34 ,, 1-Amino-3-acetylamino-benzene 35 ,, 1 -Am ino-3-methyl-6-methoxybenzene 36 " 1 -Amino-3-ureido-6-methylbenzene 37 " N-Ethylaniline 38 1 -Ethylamino-3-methylbenzene 39 ,, 1 -Amino-2-methylbenzene 40 1 -Amino-2,5-dimethylbenzene 41 2-Aminonaphthalene-5,7- Aminobenzene
disulphonic acid 42 " 1-Amino-3-methylbenzene 43 " 3-Aminophenylurea 44 " 1-Amino-3-hydroxyacetylaminobenzene 45 " 1-Amino-3-methaneacetylamino-benzene 46 " 1-Amino-2,5-dimethoxybenzene 47 " 1-Amino-3-methyl-6-methoxybenzene 48 " 1-Amino-3-ureido-6-methylbenzene 49 ,, N-Ethylaniline 50 " 1-Ethylamino-3-methylbenzene 51 " 1-Amino-2-methylbenzene 52 " 1-Amino-2,5-dimethylbenzene 53 2-Aminonaphthalene-4,8- Aminobenzene
disulphonic acid 54 ,, 1-Amino-3-methylbenzene 55 ,, 3-Aminophenylurea 56 " 1 -Amino-3-hydroxyacetylam ino-benzene 57 " 1-Amino-3-acetylamino-6-methoxy-benzene 58 " 1-Amino-3-acetylamino-6-methyl-benzene 59 ,, 1 -Am ino-3-acetylam ino-benzene 60 " 1-Amino-3-methyl-6-methoxybenzene 61 " 1-Amino-3-ureido-6-methylbenzene 62 " N-Ethylaniline 63 " 1-Ethylamino-3-methylbenzene 64 " 1-Amino-2-methylbenzene 65 " 1-Amino-2,5-dimethylbenzene 66 2-Aminonaphthalene-4-,6,8- Aminobenzene
trisulphonic acid 67 1 -Amino-3-methylbenzene 68 " 3-Aminophenylurea 69 " 1 -Ami no-3-hydroxyacetylam ino-benzene 70 " 1-Amino-3-acetylamino-6-methoxy-benzene 71 " 1 -Amino-3-acetyla m ino-6-methylbenzene 72 " 1 -Am ino-3-acetyla minobenzene AMINOAZO COMPOUND FROM
No.Diazo component Coupling component 73 " 1-Amino-3-methyl-6-methoxybenzene 74 ,, 1-Amino-3-ureido-6-methylbenzene 75 " N-Ethylaniline 76 " 1-Ethylamino-3-methylbenzene 77 ,, " 1 1-Amino-2-methylbenzene 78 " 1-Amino-2,5-dimethylbenzene 79 2-Aminonaphthalene-3,6,8- Aminobenzene
trisulphonic acid 80 " 1-Amino-3-methylbenzene 81 " 1-Amino-3-hydroxyacetylaminobenzene 82 1 -Amino-3-acetylamino-6-methoxybenzene 83 " 1-Amino-3-acetylamino-6-methylbenzene 84 " 1-Amino-3-acetylaminobenzene 85 " 1-Amino-3-methyl-6-methoxybenzene 86 " 1-Amino-3-ureido-6-methylbenzene 87 " N-Ethylaniline 88 " 1-Ethylamino-3-methylbenzene 89 " 1-Amino-2-methylbenzene 90 " 1-Amino-2,5-dimethylbenzene 91 1-Aminobenzene-2,5- Aminobenzene
disulphonic acid 92 " 1-Amino-3-methylbenzene 93 ,, 3-Aminophenylurea 94 " 1-Amino-3-hydroxyacetylaminobenzene 95 " 1-Amino-3-acetylamino-6-methoxybenzene 96 1 -Amino-3-acetylamino-6-methylbenzene 97 ,, 1 -Amino-3-acetylaminobenzene 98 " 1 -Amino-3-methyl-6-methoxybenzene 99 ,, 1-Amino-3-ureido-6-methylbenzene 100 " N-Ethylaniline 101 1 1-Ethylamino-3-methylbenzene 102 " 1-Amino-2-methylbenzene 103 1 -Amino-2,5-dimethylbenzene 104 Aniline-2,4-disulphonic Aminobenzene
acid 105 1 1-Amino-3-methylbenzene 106 " 3-Aminophenylurea 107 " 1-Amino-3-hydroxyacetylaminobenzene 108 " 1 -Amino-3-acetylamino-6-methoxybenzene 109 " 1-Amino-3-acetylamino-6-methylbenzene 110 " 1-Amino-3-acetylaminobenzene 111 " 1 -Amino-3-methyl-6-methoxybenzene 112 " 1-Amino-3-ureido-6-methylbenzene 113 " N-Ethylaniline 114 " 1-Ethylamino-3-methylbenzene 115 1 1-Amino-2-methylbenzene 116 " 1-Amino-2,5-dimethylbenzene 117 1-Amino-2,5-disulpho-4- Aminobenzene
methoxy-benzene 118 " 1-Amino-3-methylbenzene 119 " 3-Aminophenylurea 120 " 1-Amino-3-hydroxyacetylaminobenzene 121 " 1-Amino-3-acetylamino-6-methoxybenzene 122 " 1-Amino-3-acetylamino-6-methyibenzene 123 " 1-Amino-3-acetylaminobenzene 124 " 1-Amino-3-methyl-6-methoxybenzene 125 " 1-Amino-3-ureido-6-methylbenzene 126 " N-Ethylaniline 127 " 1 -Ethylamino-3-methylbenzene 128 " 1-Amino-2-methylbenzene 129 " 1 -Amino-2,5-dimethylbenzene (Continued)
AMINAZO COMPOUND FROM
No.Diazo component Coupling component 130 1-Amino-2,4-disulpho-6- Aminobenzene
methyl-benzene 131 " 1-Amino-3-methylbenzene 132 " 3-Aminophenylurea 133 " 1-Amino-3-hydroxyacetylaminobenzene 134 " 1-Amino-3-acetylamino-6-methoxybenzene 135 " 1 -Amino-3-acetyla mino-6-methyl benzene 136 " 1-Amino-3-acetylaminobenzene 137 " 1-Amino-3-methyl-6-methoxybenzene 138 " 1-Amino- -u reido-6-methylbenzene 139 " N-Ethylaniline 140 " -Ethylamino-3-methylbenzene 141 " 1-Amino-2-methyíbenzene 142 1 -Amino-2,5-dimethylbenzene 143 1-Amino-benzene-4- Aminobenzene
sulphonic acid 144 " 1-Amino-3-methyíbenzene 145 " 3-Aminophenylurea 146 " 1-Amino-3-hydroxyacetylaminobenzene 147 " 1 -Amino-3-acetyla mino-6-methoxybenzene 148 " 1 -Amino-3-acetyla mino-6-methylbenzene 149 " 1-Amino-3-acetylaminobenzene 150 " 1-Amino-3-methyl-6-methoxybenzene 151 " 1-Amino-3-ureido-6-methylbenzene 152 " N-Ethylaniline 153 " 1-Ethylamino-3-methylbenzene 154 " 1 -Amino-2-methylbenzene 155 " 1 -Amino-2,5-dimethylbenzene
Claims (17)
1. A dyestuff of the general formula
in which the benzene ring or naphthalene ring A optionally contains further substituents, in addition to sulpho groups,
R denotes a hydrogen atom of a C1-C4 alkyl group,
R1 and F2 independently denote a hydrogen atom or an optionally substituted alkyl or cycloalkyl group, or
R1 and F2 form a ring with the nitrogen atom, optionally with the inclusion of a further hetero-atom, R3 denotes a hydrogen atom or a Ca-C4 alkyl or acylamino group,
R4 denotes a hydrogen atom or a C1-C4 alkyl, C1-C4 alkoxy, carboxyl or sulpho group, and n is 1,2 or 3.
2. A dyestuff according to claim 1, in which F3 denotes an optionally substituted (C1 -C4 alkyl)carbonylamino, arylcarbonylamino, formylamino, oxalylamino or optionally substituted ureido group.
3. A dyestuff according to claim 1 of the general formula
in which R, R1, R2, R3, R4, and n have the same meanings in claim 1.
4. A dyestuff according to claim 1 of the general formula
in which R, F1, R2, R3 and R4 have the same meanings as in claim 1 and m is 1 or 2.
5. A dyestuff according to claim 1 of the general formula
in which R1, R2 and n have the same meanings as in Claim 1 and F5 denotes acetylamino or ureido group.
6. A dyestuff according to claim 1 of the general formula
in which R1 and R2 have the same meanings as in Claim 1, m has the same meaning as in Claim 3 and F5 has the same meaning as in claim 5.
7. A dyestuff according to any of the foregoing claims, in which R1 denotes a hydrogen atom, and R2 denotes a hydrogen atom or an alkyl or cycloalkyl group.
8. A dyestuff according to any of claims 1 to 5, in which R1 and R2 denote a C2 to C6 alkyl group or together complete an optionally heteroatom-containing 5-membered or 6-membered ring.
9. A dyestuff according to any of claims 1 to 5, in which R1 and R2 denote hydrogen atoms.
10. A dyestuff according to claim 1 substantially as herein before specifically identified.
11. A process for the production of a dyestuff as claimed in Claim 1, in which a dyestuff of the general formula
in which R,R3, R4, A and n have the same meanings as in claim 1, is subjected to a condensation reaction with 2,4,6-trifluoro-1,3,5-triazine, hydrofluoric acid being split off, and the resulting difluoro compound is reacted with an amine of the general formula
in which R1 and R2 have the same meanings as in claim 1 hydrofluoric acid being split off.
12. A process for the production of a dyestuff as claimed in claim 1, in which a dyestuff of formula (VI), as defined in claim 11, is reacted with an aminodifluorotriazine of the general formula
in which R1 and R2 have the same meanings as in claim 1, hydrofluoric acid being split off.
13. A process for the production of a dyestuff as claimed in claim 1, when carried out substantially as described in anyone of the Examples.
14. A dyestuff as claimed in claim 1 when produced by the process of any of claims 11 to 13.
15. A process for dyeing or printing a material containing hydroxyl groups or amino groups comprising treating the material with a dyestuff as claimed in any of claims 1 to 10 and 14.
16. A process according to claim 15 when carried out substantially as described in the "Printing
Instructions", "Padding Instructions" or "Dyeing Instructions" of Example 1.
17. A material containg hydroxyl groups or amino groups when dyed or printed by the process of claim 15Or16.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782840380 DE2840380C2 (en) | 1978-09-16 | 1978-09-16 | Fiber-reactive azo dyes |
| DE19782842687 DE2842687A1 (en) | 1978-09-30 | 1978-09-30 | Fibre-reactive aromatic azo dyes - contg. amino-fluoro-triazinyl gps., give good wet and light fastness |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2031932A true GB2031932A (en) | 1980-04-30 |
| GB2031932B GB2031932B (en) | 1982-11-10 |
Family
ID=25775748
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7931489A Expired GB2031932B (en) | 1978-09-16 | 1979-09-11 | Fibre-reactive azo dyestuffs |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH656503GA3 (en) |
| FR (1) | FR2436166B1 (en) |
| GB (1) | GB2031932B (en) |
| IT (1) | IT7925741A0 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2127840A (en) * | 1982-09-13 | 1984-04-18 | Sandoz Ltd | Chloro-triazinyl monoazo compounds |
| EP0432542A2 (en) * | 1989-12-06 | 1991-06-19 | Bayer Ag | Azo dyestuffs and intermediates for their preparation |
| US5128456A (en) * | 1989-11-01 | 1992-07-07 | Ciba-Geigy Corporation | Reactive dyes |
| US5132410A (en) * | 1989-12-06 | 1992-07-21 | Bayer Aktiengesellschaft | Azo reactive dyestuffs containing a fluorotriazinyl group |
| US5227478A (en) * | 1982-09-13 | 1993-07-13 | Sandoz Ltd. | 2-chloro-4-[4'-(4",8"-disulfonaphth-2"-ylazo)-2'-methoxy-5'-methylanilino]-6 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3045789A1 (en) * | 1980-12-04 | 1982-07-22 | Bayer Ag, 5090 Leverkusen | FIBER ACTIVE AZO DYES, METHOD FOR THEIR PRODUCTION AND THEIR USE FOR COLORING AND PRINTING FIBER MATERIALS CONTAINING HYDROXYL GROUPS AND / OR NITROGEN |
| DE3149129A1 (en) * | 1981-12-11 | 1983-06-16 | Bayer Ag, 5090 Leverkusen | LIQUID CRYSTALLINE PHASE OF AN AZOREACTIVE DYE AND THE USE THEREOF FOR COLORING AND PRINTING NATURAL AND SYNTHETIC SUBSTRATES |
| EP0230210B1 (en) * | 1985-12-23 | 1989-12-13 | Ciba-Geigy Ag | Reactive dyes, their preparation and their use |
| GB9204905D0 (en) * | 1992-03-06 | 1992-04-22 | Ici Plc | Compositions and compounds |
| BR9300742A (en) * | 1992-03-06 | 1993-09-28 | Zeneca Ltd | HIGH CONCENTRATION WATER SOLUTION, COMPOSITION, COMPOUND AND PROCESS |
-
1979
- 1979-09-11 GB GB7931489A patent/GB2031932B/en not_active Expired
- 1979-09-13 CH CH831279A patent/CH656503GA3/de unknown
- 1979-09-14 FR FR7922956A patent/FR2436166B1/en not_active Expired
- 1979-09-14 IT IT7925741A patent/IT7925741A0/en unknown
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2127840A (en) * | 1982-09-13 | 1984-04-18 | Sandoz Ltd | Chloro-triazinyl monoazo compounds |
| US5227478A (en) * | 1982-09-13 | 1993-07-13 | Sandoz Ltd. | 2-chloro-4-[4'-(4",8"-disulfonaphth-2"-ylazo)-2'-methoxy-5'-methylanilino]-6 |
| US5128456A (en) * | 1989-11-01 | 1992-07-07 | Ciba-Geigy Corporation | Reactive dyes |
| EP0432542A2 (en) * | 1989-12-06 | 1991-06-19 | Bayer Ag | Azo dyestuffs and intermediates for their preparation |
| US5132410A (en) * | 1989-12-06 | 1992-07-21 | Bayer Aktiengesellschaft | Azo reactive dyestuffs containing a fluorotriazinyl group |
| US5278293A (en) * | 1989-12-06 | 1994-01-11 | Bayer Aktiengesellschaft | Azo dyestuffs and intermediate products for their preparation |
| EP0432542B1 (en) * | 1989-12-06 | 1994-09-14 | Bayer Ag | Azo dyestuffs and intermediates for their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2436166B1 (en) | 1985-07-19 |
| GB2031932B (en) | 1982-11-10 |
| FR2436166A1 (en) | 1980-04-11 |
| CH656503GA3 (en) | 1986-07-15 |
| IT7925741A0 (en) | 1979-09-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PE20 | Patent expired after termination of 20 years |
Effective date: 19990910 |