GB2030591A - Azo reactive dyestuffs - Google Patents
Azo reactive dyestuffs Download PDFInfo
- Publication number
- GB2030591A GB2030591A GB7930436A GB7930436A GB2030591A GB 2030591 A GB2030591 A GB 2030591A GB 7930436 A GB7930436 A GB 7930436A GB 7930436 A GB7930436 A GB 7930436A GB 2030591 A GB2030591 A GB 2030591A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dyestuff
- denotes
- acid
- general formula
- sulpho
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 carboxyl sulpho Chemical class 0.000 claims abstract description 22
- 238000004043 dyeing Methods 0.000 claims abstract description 8
- 239000000463 material Substances 0.000 claims abstract description 6
- 125000003368 amide group Chemical group 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 239000000975 dye Substances 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 15
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 238000006482 condensation reaction Methods 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 230000007935 neutral effect Effects 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000000835 fiber Substances 0.000 claims 2
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract description 2
- 239000004952 Polyamide Substances 0.000 abstract description 2
- 239000004744 fabric Substances 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 229920002647 polyamide Polymers 0.000 abstract description 2
- 229920002635 polyurethane Polymers 0.000 abstract description 2
- 239000004814 polyurethane Substances 0.000 abstract description 2
- 239000004627 regenerated cellulose Substances 0.000 abstract description 2
- 239000004753 textile Substances 0.000 abstract description 2
- 238000005406 washing Methods 0.000 abstract description 2
- 210000002268 wool Anatomy 0.000 abstract description 2
- 206010016654 Fibrosis Diseases 0.000 abstract 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 9
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 5
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 5
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 5
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UCTREIIEJSFTDI-UHFFFAOYSA-N 3-aminonaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1 UCTREIIEJSFTDI-UHFFFAOYSA-N 0.000 description 3
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 3
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- JSBQMQFABBMNSV-UHFFFAOYSA-N 4-aminonaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 JSBQMQFABBMNSV-UHFFFAOYSA-N 0.000 description 2
- HRXZRAXKKNUKRF-UHFFFAOYSA-N 4-ethylaniline Chemical compound CCC1=CC=C(N)C=C1 HRXZRAXKKNUKRF-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- QIKYZXDTTPVVAC-UHFFFAOYSA-N 4-Aminobenzamide Chemical compound NC(=O)C1=CC=C(N)C=C1 QIKYZXDTTPVVAC-UHFFFAOYSA-N 0.000 description 1
- XVLPAXBBSDOYAF-UHFFFAOYSA-N 4-[(4,6-difluoro-1,3,5-triazin-2-yl)amino]benzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1NC1=NC(F)=NC(F)=N1 XVLPAXBBSDOYAF-UHFFFAOYSA-N 0.000 description 1
- QUFFRITXLMVPMV-UHFFFAOYSA-N 4-aminonaphthalene-1,6-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 QUFFRITXLMVPMV-UHFFFAOYSA-N 0.000 description 1
- NDYYJXGERWTRSD-UHFFFAOYSA-N 4-aminonaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 NDYYJXGERWTRSD-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- MLNFMFAMNBGAQT-UHFFFAOYSA-N 4-propan-2-yloxyaniline Chemical compound CC(C)OC1=CC=C(N)C=C1 MLNFMFAMNBGAQT-UHFFFAOYSA-N 0.000 description 1
- DQNAQOYOSRJXFZ-UHFFFAOYSA-N 5-Amino-1-naphthalenesulfonic acid Chemical compound C1=CC=C2C(N)=CC=CC2=C1S(O)(=O)=O DQNAQOYOSRJXFZ-UHFFFAOYSA-N 0.000 description 1
- UWPJYQYRSWYIGZ-UHFFFAOYSA-N 5-aminonaphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC=CC2=C1 UWPJYQYRSWYIGZ-UHFFFAOYSA-N 0.000 description 1
- ZBGXGVYIKJFNAT-UHFFFAOYSA-N 6-aminonaphthalene-1,3,5-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=C(S(O)(=O)=O)C(N)=CC=C21 ZBGXGVYIKJFNAT-UHFFFAOYSA-N 0.000 description 1
- KZCSUEYBKAPKNH-UHFFFAOYSA-N 6-aminonaphthalene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KZCSUEYBKAPKNH-UHFFFAOYSA-N 0.000 description 1
- HKTWHHAJDJCUPC-UHFFFAOYSA-N 7-aminonaphthalene-1,3,5-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 HKTWHHAJDJCUPC-UHFFFAOYSA-N 0.000 description 1
- GFPQSWFFPRQEHH-UHFFFAOYSA-N 7-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1S(O)(=O)=O GFPQSWFFPRQEHH-UHFFFAOYSA-N 0.000 description 1
- CMOLPZZVECHXKN-UHFFFAOYSA-N 7-aminonaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 CMOLPZZVECHXKN-UHFFFAOYSA-N 0.000 description 1
- FYVOTMMSGKWFPK-UHFFFAOYSA-N 7-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC=C21 FYVOTMMSGKWFPK-UHFFFAOYSA-N 0.000 description 1
- QEZZCWMQXHXAFG-UHFFFAOYSA-N 8-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1 QEZZCWMQXHXAFG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 1
- NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Dyestuffs of the formula <IMAGE> wherein D is a radical of a naphthalene mono-, di- or tri-sulphonic acid, R is H, methyl or ethyl, and X is H, halogen, C1-C4 alkyl, C1-C4 alkoxy, carboxyl sulpho or acylamino, and their use for dyeing and printing materials containing hydroxyl groups or amide groups, such as textile fibres, filaments and fabrics of wool, silk or synthetic polyamide and polyurethane fibros, and for dyeing and printing natural or regenerated cellulose with dyeings and prints which are fast to washing.
Description
SPECIFICATION
Azo reactive dyestuffs
The present invention relates to azo reactive dyestuffs of the formula
wherein
D= the radical of a naphthalene-mono-, -di- or -tri-sulphonic acid,
R=hydrogen, methyl or ethyl and
X=hydrogen, C1-C4-alkyl, C1-C4-alkoxy, halogen, such as fluorine, chlorine or bromine, or a
carboxyl, sulpho or acylamino group, such as acetylamino, ureido, formylamino or oxalylamino.
Examples of a mines of the formula D-NH2 (Il) are the following: 2-amino-naphthalene-1 -sulphonic acid, 2-amino-naphthalene-1 5-disulphonic acid, 2-amino-naphthalene- 1 ,5,7-trisulphonic acid, 2-amino-naphthalene-3,6-disulphonic acid, 2-aminonaphthalene-3,6,8-trisulphonic acid, 2-amino-naphthalene-4,8-disu Iphonic acid, 2-amino-naphthalene4,6,8-trisulphonic acid, 2-a mino-naphthalene-5,7-disulphon ic acid, 2-a mino-naphthalene-6,8disulphonic acid, 2-amino-naphthaíene-6-sulphonic acid, 2-amino-naphthalene-8-sulphonic acid, 1amino-naphthalene-4-sulphonic acid, 1 -amino-naphthalene-5-sulphonic acid, 1 -amino-naphthalene-6- sulphonic acid, 1 -amino-naphthalene-7-sulphonic acid, 1 -amino-naphthalene-4,6-disulphonic acid, 1 a mino-naphtha lene-4.7-disulphonic acid, 1 -amino-naphtha lene-3,6-disulphonic acid, 2-am ino-6-nitro- naphthalene-4,8-disulphonic acid and 2-a mino-6-acetylamino-naphthalene-4,8-disu Iphonic acid.
Preferred compounds correspond to the formulae
wherein
R and X have the meaning indicated above and R,=hydrogen or suipho, and
wherein
R, R, and X have the meaning indicated above.
Compounds of the formulae (Ill) and (IV) in which
a) X=hydrogen,
b) X=sulpho,
c) X and R=hydrogen, or
d) X=sulpho and
R=hydrogen, are particularly preferred.
The invention furthermore relates to a processforthe preparation of the compounds of the formula (I). It consists of a procedure in which dyestuffs of the formula
wherein
D and R have the meaning indicated above, are subjected to condensation reactions 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
wherein
X has the meaning indicated above, hydrofluoric acid being split off, to give (I).
The condensation of the dyestuffs (V) 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 (VI) is likewise 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 neutralised by adding aqueous alkali metal hydroxides, carbonates or bicarbonates. In general, isolation of the difluoro compound is dispensed with.
In the case where X=sulpho or carboxyl, the dyestuffs (I) can also be prepared by a process in which p-sulphanilic acid or 4-carboxy-aniline is first reacted with s-trifluorotriazine and the condensation with the dyestuff (V) is then carried out.
A further possibility for the preparation of (I) consists of a process in which diazotised amines (II) are combined with coupling components of the formula
wherein
X and R have the meaning indicated above,
in a weakly acid, neutral to weakly alkaline range.
The dyestuffs (V) are obtained by coupling the diazotised amines (II) with I-acid under such
conditions that the coupling preferably takes place in the o-position reiative to the hydroxyl group of the
I-acid. However, coupling with a N-acylated I-acid is in general preferred, the acyl radical subsequently
being split off by warming in an acid or alkaline medium. Possible acyl radicals are, in particular, acetyl, ca rba moyl, methoxycarbonyl, ethoxycarbonyl or--COO-(l-acid urea by reaction with phosgene).
Examples of amines (VI) are the following: aniline, 4-methyl-aniline, 4-ethyl-aniline, 4-iso-propylaniline, 4-methoxy-aniline, 4-ethoxy-aniline, 4-iso-propoxy-aniline, 4-fluoroaniline, 4-chloroaniline, 4bromoaniline, 4-ca rboxy-aniline, 4-sulpho-aniline, 4-acetylamino-aniline or 4-carbamoyl-aniline.
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 or synthetic 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
55.3 g of the dyestuff of the formula 1 ,5-disulpho-naphthalenet 2 azo 2 21 -hydroxy-3-su Ipho-6amino-naphthaiene are dissolved in a mixture of 400 ml of water and 200 g of ice. 14 g of strifluorotriazine are then added dropwise and a pH value of 3.5-4.5 is simultaneously maintained by adding 20% strength sodium carbonate solution. When the acylation reaction has ended, 9.3 g of aniline are added, the pH value is adjusted to 6 with 20% strength sodium carbonate solution and the mixture is stirred at pH 6 until the second condensation reaction has ended. The temperature is 0--100.
The dyestuff is separated out by adding sodium chloride, filtered off dried and ground. A light red powder which dissolves in water giving an orange-coloured solution results. The dyestuff corresponds to the formula
Example Column 1 Column 2 Column 3 Column 4 2 2-amino-1,5-disulphonaphthalene 1-hydroxy-3-sulpho-6-amino- p-sulphanilic acid orange naphthalene 3 " " 4-carboxy-aniline " 4 " " p-aniline " 5 " " p-toluidine " 6 " " p-chloroaniline " 7 " " p-fluoroaniline " 8 " 1-hydroxy-3-sulpho-6-methylamino- aniline " maphthalene 9 " " p-toluidine " 10 " " p-anisidine " 11 " " p-phenetidine " 12 " " p-chloroaniline " 13 2-amino-1,5,7-trisulphoaniline 1-hydroxy-3-sulpho-6-amino- aniline " naphthalene 14 " " p-toluidine " 15 " " p-anisidine " 16 " " p-phenetidine " 17 " " p-chloroaniline " 18 " " p-fluoroaniline " 19 2-amino-3,6-disulphonaphthalene " aniline scarlet 20 " " p-sulphanilic acid " Example Column 1 Column 2 Column 3 Column 4 21 2-amino-3,6-disulphonaphthalene 1-hydroxy-3-sulpho-6-smino- 4-carboxyaniline scarlet naphthalene 22 " " p-anisidine " 23 2-amino-3,6,8-trisulphoaniline " aniline " 24 " " p-toluidine " 25 " " p-anisidine " 26 " " p-chloroaniline " 27 " " 2-amino-3,6-disulphonaphthalene 1-hydroxy-3-sulpho-6-methylamino- aniline " naphthalene 28 " 1-hydroxy-3-sulpho-6-ethylamino- aniline " naphthalene 29 2-amino-4,6,8-trisulphonaphthalene 1-hydroxy-3-sulpho-6-amino- aniline red naphthalene 30 " " p-toluidine " 31 2-amino-4,8-disulphonaphthalene " aniline " 32 " " p-sulphanilic acid " 33 2-amino-5,7-disulphonaphthalene " p-sulphanilic acid " 34 2-amino-6,8-disulphonaphthalene " p-sulphanilic acid " 35 1-amino-4,7-disulphonaphthalene " p-sulphanilic acid " 36 1-amino-4,6-disulphonaphthalene " p-sulphanilic acid " 37 1-amino-3,6-disulphonaphthalene " p-sulphanilic acid " EXAMPLE 38
55.3 g of the dyestuff of the formula 1 ,5-disulpho-naphthalene( 2 azo 2 1 -hydroxy-3-sulpho-6amino-naphthalene are stirred in a mixture of 300 ml of water and 100 g of ice. An ice-cold aqueous solution of 28.8 g of 2,4-difluoro-6-(4'-sulphophenylamino)-1 ,3,5-triazine is then added and the condensation reaction is carried out in the pH range of 5 to 6 and in the temperature range of O to 150. The dyestuff is salted out, filtered off, dried and ground. The dyestuff is identical to the product obtained according to Example 2).
Claims (15)
1. A dvestuffofthe aeneral formula
in which
D denotes a radical of a naphthalene-mono-, -di- or -tri-sulphonic acid,
R denotes a hydrogen atom or a methyl or ethyl group and
X denotes a hydrogen or a halogen atom or a C, to C4 alkyl, C to C4 alkoxy, carboxyl, sulpho or acylamino group.
2. A dyestuff according to claim 1 in which X denotes a fluorine, chlorine or bromine atom.
3. A dyestuff according to claim 1 of the general formula
in which
R and X have the same meanings as in claim 1 and
R1 denotes a hydrogen atom or a sulpho group.
4. A dyestuff according to claim 1 of the general formula
in which
R and X have the same meanings as indicated in claim 1 and R, has the same meaning as in claim 2.
5. A dyestuff according to claim 3 or 4 in which X denotes a hydrogen atom.
6. A dyestuff according to claim 3 or 4 in which X denotes a sulpho group.
7. A dyestuff according to claim 3 or 4 in which X and R denote hydrogen atoms.
8. A dyestuff according to claim 3 or 4 in which X denotes a sulpho group and R denotes a hydrogen atom.
9. A dyestuff according to claim 1 as herein before specifically identified.
1 0. A process for the production of a dyestuff as claimed in claim 1 in which a dyestuff of the general formula.
In welch U and H have the same meanings as in claim 1, is reacted with 2,4,6-trifluoro-1 3,5-triazine, 1 mol of hydrofluoric acid being split off, and the resulting difluoro compound is subjected to a condensation reaction with an amines of the general formula
in which X has the same meaning as in claim 1, 1 mol of hydrofluoric acid being split off.
1 1. A process for the production of a dyestuff as claimed in claim 1 in which an amineofthe general formula D-NH2 (II) in which D has the same meaning as in claim 1, is diazotised and coupled with a coupling component of the general formula
in which X and R have the same meanings as in claim 1, in a weakly acid, neutral to weakly alkaline range.
12. A process for the production of a dyestuff as claimed in claim 1 when carried out substantially as described in any one of the Examples.
13. A dyestuff as claimed in claim 1 when produced by the process of any of claims 10to 12.
14. A process for dyeing or printing a fibre material containing hydroxyi groups or amide groups comprising treating the material with a dyestuff as claimed in any of claims 1 to 9 and 13.
15. A fibre material containing hydroxyl groups or amide groups when dyed or printed by the process of claim 14.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782838608 DE2838608A1 (en) | 1978-09-05 | 1978-09-05 | AZO REACTIVE DYES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2030591A true GB2030591A (en) | 1980-04-10 |
| GB2030591B GB2030591B (en) | 1982-11-03 |
Family
ID=6048684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7930436A Expired GB2030591B (en) | 1978-09-05 | 1979-09-03 | Azo reactive dyestuffs |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5536291A (en) |
| CH (1) | CH661740A5 (en) |
| DE (1) | DE2838608A1 (en) |
| FR (1) | FR2435509B1 (en) |
| GB (1) | GB2030591B (en) |
| IT (1) | IT7925447A0 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0074557A2 (en) * | 1981-09-10 | 1983-03-23 | Bayer Ag | Reactive azo dyestuffs |
| GB2128200A (en) * | 1982-09-17 | 1984-04-26 | Sandoz Ltd | Chloro-triazinyl mondazo compounds |
| US5149791A (en) * | 1989-11-01 | 1992-09-22 | Ciba-Geigy Corporation | Chlorotriazine reactive dyes having a 4-methoxy-2-sulfoaniline diazo component and 2-amino-5-naphthol-7-sulfonic acid coupling component |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2847916C2 (en) * | 1978-11-04 | 1984-04-26 | Basf Ag, 6700 Ludwigshafen | Reactive dyes and their use |
| CN104559320A (en) * | 2014-04-28 | 2015-04-29 | 无锡润新染料有限公司 | Composite active brilliant orange dye composition |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE638184A (en) * | 1962-10-04 | 1900-01-01 | ||
| DE1644208C3 (en) * | 1967-04-19 | 1978-06-01 | Bayer Ag, 5090 Leverkusen | Reactive dyes |
| IT1116356B (en) * | 1976-07-12 | 1986-02-10 | Ciba Geigy Ag | REACTIVE AZO DYES FOR FIBERS AND PROCEDURE FOR THEIR PRODUCTION AND APPLICATION |
| LU78115A1 (en) * | 1977-09-12 | 1979-05-23 | Ciba Geigy Ag | AZO DYES, THEIR PRODUCTION AND USE |
| CH641197A5 (en) * | 1977-12-23 | 1984-02-15 | Sandoz Ag | REACTIVE MONOAZO DYES AND METHOD FOR THE PRODUCTION THEREOF. |
-
1978
- 1978-09-05 DE DE19782838608 patent/DE2838608A1/en active Granted
-
1979
- 1979-09-03 IT IT7925447A patent/IT7925447A0/en unknown
- 1979-09-03 JP JP11181679A patent/JPS5536291A/en active Pending
- 1979-09-03 GB GB7930436A patent/GB2030591B/en not_active Expired
- 1979-09-04 FR FR7922096A patent/FR2435509B1/en not_active Expired
- 1979-09-04 CH CH3902/86A patent/CH661740A5/en not_active IP Right Cessation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0074557A2 (en) * | 1981-09-10 | 1983-03-23 | Bayer Ag | Reactive azo dyestuffs |
| EP0074557A3 (en) * | 1981-09-10 | 1983-06-22 | Bayer Ag | Reactive azo dyestuffs |
| GB2128200A (en) * | 1982-09-17 | 1984-04-26 | Sandoz Ltd | Chloro-triazinyl mondazo compounds |
| US5149791A (en) * | 1989-11-01 | 1992-09-22 | Ciba-Geigy Corporation | Chlorotriazine reactive dyes having a 4-methoxy-2-sulfoaniline diazo component and 2-amino-5-naphthol-7-sulfonic acid coupling component |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2435509B1 (en) | 1985-07-19 |
| IT7925447A0 (en) | 1979-09-03 |
| GB2030591B (en) | 1982-11-03 |
| DE2838608C2 (en) | 1988-01-14 |
| DE2838608A1 (en) | 1980-03-20 |
| JPS5536291A (en) | 1980-03-13 |
| CH661740A5 (en) | 1987-08-14 |
| FR2435509A1 (en) | 1980-04-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |