DE1544368B - Water-insoluble monoazo dyes, process for their preparation and their use - Google Patents
Water-insoluble monoazo dyes, process for their preparation and their useInfo
- Publication number
- DE1544368B DE1544368B DE1544368B DE 1544368 B DE1544368 B DE 1544368B DE 1544368 B DE1544368 B DE 1544368B
- Authority
- DE
- Germany
- Prior art keywords
- red
- ruby
- dyes
- parts
- alkyl
- 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.)
- Pending
Links
- 239000000975 dye Substances 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title description 3
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title description 2
- 238000000034 method Methods 0.000 title description 2
- -1 acetoxy, acetylamino, carbomethoxy, carboethoxy, methoxy Chemical group 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001436 propyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical group ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 239000010979 ruby Substances 0.000 description 17
- 229910001750 ruby Inorganic materials 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YLNDNABNWASMFD-UHFFFAOYSA-N 4-[(1,3-dimethylimidazol-1-ium-2-yl)diazenyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1N=NC1=[N+](C)C=CN1C YLNDNABNWASMFD-UHFFFAOYSA-N 0.000 description 10
- 230000008878 coupling Effects 0.000 description 9
- 238000010168 coupling process Methods 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 8
- 206010039587 Scarlet Fever Diseases 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- 244000172533 Viola sororia Species 0.000 description 2
- 229940081735 acetylcellulose Drugs 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- VYJSGJXWKSDUSG-UHFFFAOYSA-N ethyl 2-amino-1,3-benzothiazole-6-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=C(N)SC2=C1 VYJSGJXWKSDUSG-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- HYVGFUIWHXLVNV-UHFFFAOYSA-N 2-(n-ethylanilino)ethanol Chemical compound OCCN(CC)C1=CC=CC=C1 HYVGFUIWHXLVNV-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- MFXBLRGWJRYPNT-UHFFFAOYSA-N 2-butoxy-1,3-benzothiazole Chemical compound C1=CC=C2SC(OCCCC)=NC2=C1 MFXBLRGWJRYPNT-UHFFFAOYSA-N 0.000 description 1
- FENJKTQEFUPECW-UHFFFAOYSA-N 3-anilinopropanenitrile Chemical compound N#CCCNC1=CC=CC=C1 FENJKTQEFUPECW-UHFFFAOYSA-N 0.000 description 1
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- 241000972773 Aulopiformes Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 244000154870 Viola adunca Species 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 238000006149 azo coupling reaction Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N cyclobenzothiazole Natural products C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- DNGZINUIRBDWED-UHFFFAOYSA-N methyl 2-amino-1,3-benzothiazole-6-carboxylate Chemical compound COC(=O)C1=CC=C2N=C(N)SC2=C1 DNGZINUIRBDWED-UHFFFAOYSA-N 0.000 description 1
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
Description
2. Ein Verfahren zur Herstellung von Färbstoffen gemäß Anspruch 1, dadurch gekennzeichnet, daß man Diazoverbindungen von Aminen der Formel2. A process for the preparation of dyes according to claim 1, characterized in that that one diazo compounds of amines of the formula
NH2 NH 2
mit Kupplungskomponenten der Formel
Zwith coupling components of the formula
Z
Die Erfindung betrifft neue wasserunlösliche Monoazofarbstoffe der allgemeinen FormelThe invention relates to new water-insoluble monoazo dyes of the general formula
IlIl
R1O-CR 1 OC
in der R1 gegebenenfalls durch Hydroxy, Chlor, Brom, Cyan oder Acetylamino substituiertes Alkyl mit 1 bisin which R 1 optionally substituted by hydroxy, chlorine, bromine, cyano or acetylamino alkyl with 1 to
IOIO
15 6 C-Atomen, R2 und R3 Wasserstoff oder gegebenenfalls durch Hydroxy oder Cyan, Chlor, Acetoxy, Acetylamino, Carbomethoxy, Carboäthoxy, Methoxy oder Äthoxy substituiertes Äthyl oder Alkyl mit 1 bis 4 C-Atomen oder gegebenenfalls durch Methoxy, Äthoxy, Carbomethoxy, Acetylamino, Dihydroxy, /ίϊ-hydroxy-y-chlor-substituiertes Propyl, mit der Maßgabe, daß höchstens einer der beiden Substituenten R2 oder R3 Wasserstoff sein kann, Y Wasserstoff, Alkyl- oder Alkoxygruppen mit 1 bis 4 C-Atomen, Trifluormethyl, Halogen oder Acylamino mit bis zu 4 C-Atomen und Z Wasserstoff oder eine Alkyl- oder Alkoxygruppe bis zu 4 C-Atomen bedeutet. 15 6 carbon atoms, R 2 and R 3 hydrogen or optionally substituted by hydroxy or cyano, chlorine, acetoxy, acetylamino, carbomethoxy, carboethoxy, methoxy or ethoxy substituted ethyl or alkyl with 1 to 4 carbon atoms or optionally by methoxy, ethoxy, Carbomethoxy, acetylamino, dihydroxy, / ίϊ-hydroxy-y-chloro-substituted propyl, with the proviso that at most one of the two substituents R 2 or R 3 can be hydrogen, Y is hydrogen, alkyl or alkoxy groups with 1 to 4 C- Atoms, trifluoromethyl, halogen or acylamino with up to 4 carbon atoms and Z denotes hydrogen or an alkyl or alkoxy group up to 4 carbon atoms.
Die neuen Farbstoffe werden in an sich bekannter Weise durch Kondensation oder Azokupplung erhalten, vorzugsweise durch Kupplung der Diazoverbindungen von Aminen der FormelThe new dyes are obtained in a manner known per se by condensation or azo coupling, preferably by coupling the diazo compounds of amines of the formula
2020th
2525th
3535
6060
R,R,
NH,NH,
(Π)(Π)
mit Verbindungen der Formel
Zwith compounds of the formula
Z
3030th
(III)(III)
4040
4545
in an sich üblicher Weise umsetzt, wobei R1, R2, R3, Y und Z die für Anspruch 1 angegebenen Bedeutungen haben.reacted in a conventional manner, where R 1 , R 2 , R 3 , Y and Z have the meanings given for claim 1.
3. Die Verwendung der Farbstoffe gemäß Anspruch 1 zum Färben von Textilmaterial aus Celluloseestern oder Polyestern.3. The use of the dyes according to claim 1 for dyeing textile material Cellulose esters or polyesters.
55 wobei R1, R2, R3, Y und Z die oben angegebenen Bedeutungen haben. 55 where R 1 , R 2 , R 3 , Y and Z have the meanings given above.
Als Reste R1 seien beispielsweise Methyl, Äthyl, Propyl, Butyl, Pentyl und Hexyl genannt. Diese Reste können Substituenten, wie eine Cyan-, Hydroxy-, Alkoxy-, Acetylamino- oder Carbalkoxygruppe sowie Chlor oder Brom tragen.Examples of radicals R 1 include methyl, ethyl, propyl, butyl, pentyl and hexyl. These radicals can carry substituents such as cyano, hydroxy, alkoxy, acetylamino or carbalkoxy, and also chlorine or bromine.
Die Reste R2 und R3 können als Substituenten beispielsweise Nitril-, Halogen-, Hydroxy-, Alkoxy-, Acyloxy- und Carbalkoxygruppen enthalten.The radicals R 2 and R 3 can contain, for example, nitrile, halogen, hydroxy, alkoxy, acyloxy and carbalkoxy groups as substituents.
Im einzelnen seien für R2 und R3 beispielsweise folgende Reste genannt: Methyl, Äthyl, Propyl, Butyl, /S-Cyanäthyl, /J-Hydroxyäthyl, ^,y-Dihydroxypropyl, β - Hydroxy - γ - chlorpropyl, Carbomethoxyäthyl, Carboäthoxyäthyl, Carbomethoxypropyl, Acetoxyäthyl, Methoxypropyl, Äthoxyäthyl, Äthoxypropyl, Methoxyäthyl, ß-Chloräthyl, Butan-3-on-l-yl.The following radicals may be mentioned for R 2 and R 3, for example: methyl, ethyl, propyl, butyl, / S-cyanoethyl, / I-hydroxyethyl, ^, y-dihydroxypropyl, β - hydroxy - γ - chloropropyl, carbomethoxyethyl, carboethoxyethyl, Carbomethoxypropyl, acetoxyethyl, methoxypropyl, ethoxyethyl, ethoxypropyl, methoxyethyl, ß-chloroethyl, butan-3-one-1-yl.
Kupplungskomponenten der Formel III zur Herstellung der neuen Farbstoffe sind beispielsweise:Coupling components of the formula III for the preparation of the new dyes are, for example:
N-Äthylaminobenzol,
N-Butylaminobenzol,
N-Cyanäthylaminobenzol,
N-Methoxyäthyl-3-methylbenzol,
N-Cyanäthyl-3-chlorbenzol,
N,N-Diäthylaminobenzol,
N-Äthyl-N-ß-hydroxyäthylaminobenzol,
N-Äthyl-N-ß-cyanoäthylaminobenzol,
N-^-Hydroxyathyl-N'/i-cyanoathylaminobenzol,
N-Äthyl-N-ß-acetoxyäthylaminobenzol,
N-Äthyl-N-^-methoxyäthylaminobenzol,
N-Zi-Acetoxyathyl-N-Zi-cyanoathylaminobenzol,
N,N-Di-(/Miydroxyäthyl)-aminobenzol,
N-^-Carbomethoxyathyl-N-^-hydroxyathylaminobenzol,
N-ethylaminobenzene,
N-butylaminobenzene,
N-cyanoethylaminobenzene,
N-methoxyethyl-3-methylbenzene,
N-cyanoethyl-3-chlorobenzene,
N, N-diethylaminobenzene,
N-ethyl-N-ß-hydroxyethylaminobenzene,
N-ethyl-N-ß-cyanoethylaminobenzene,
N - ^ - Hydroxyethyl-N '/ i-cyanoathylaminobenzene, N-Ethyl-N-ß-acetoxyäthylaminobenzol,
N-ethyl-N - ^ - methoxyethylaminobenzene,
N-Zi-Acetoxyethyl-N-Zi-cyanoathylaminobenzol, N, N-Di - (/ Miydroxyäthyl) -aminobenzol,
N - ^ - Carbomethoxyathyl-N - ^ - hydroxyathylaminobenzene,
N-^-Acetoxyathyl-N-p'-hydroxyathylamino-N - ^ - Acetoxyathyl-N-p'-hydroxyathylamino-
benzol,
N-^-Methoxyäthyl-N-^-hydroxyäthylaminobenzol,
benzene,
N - ^ - methoxyethyl-N - ^ - hydroxyethylaminobenzene,
N'/i-Methoxyathyl-N-^-cyanoathylaminobenzol, N-^-Methoxyathyl-N-zJ-carbomethoxyathyl-N '/ i-Methoxyethyl-N - ^ - cyanoathylaminobenzene, N - ^ - Methoxyethyl-N-zJ-carbomethoxyathyl-
aminobenzol,
N-/i-Methoxyäthyl-N-/:i-acetoxyäthylamino-aminobenzene,
N- / i-Methoxyäthyl-N - /: i-acetoxyäthylamino-
benzol,
N-/3-Methoxyäthyl-N-(butan-3-on-1 -yl)-aminobenzol,
benzene,
N- / 3-methoxyethyl-N- (butan-3-one-1 -yl) -aminobenzene,
N-Äthyl-N-zj-cyanoäthyl-S-methylaminobenzol, N-Athyl-N-zS-hydroxyathyl-S-methylamino-N-ethyl-N-zj-cyanoethyl-S-methylaminobenzene, N-ethyl-N-zS-hydroxyethyl-S-methylamino-
benzol,
N-Äthyl-N-y-acetylaminopropyl-3-methylaminobenzol,
benzene,
N-ethyl-Ny-acetylaminopropyl-3-methylaminobenzene,
N,N-Di-(/9-hydroxyäthyl)-3-methylaminobenzol, N-ß-Cyanoäthyl-N-ß-hydroxyäthyl-S-methyl-N, N-Di - (/ 9-hydroxyethyl) -3-methylaminobenzene, N-ß-cyanoethyl-N-ß-hydroxyethyl-S-methyl-
aminobenzol,
N-ß-Cyanoäthyl-N-ß-methoxyäthyl-S-methylaminobenzol,
aminobenzene,
N-ß-cyanoethyl-N-ß-methoxyethyl-S-methylaminobenzene,
N-ß-Cyanoäthyl-N-butyl-ß-methylaminobenzol, N-ß-Hydroxyäthyl-N-butyl-S-methylaminobenzol, N-ß-cyanoethyl-N-butyl-ß-methylaminobenzene, N-ß-hydroxyethyl-N-butyl-S-methylaminobenzene,
N-ß-Chloräthyl-N-butyl-S-methylaminobenzol, N-ß-Chloräthyl-N-ß-methoxyäthyW-methylaminobenzol, N-ß-chloroethyl-N-butyl-S-methylaminobenzene, N-ß-chloroethyl-N-ß-methoxyäthyW-methylaminobenzene,
N^-Di-^-hydroxyäthy^-S-chloraminobenzol, N-^-Hydroxyathyl-N-^-cyanoathyl-S-chlor-N ^ -Di - ^ - hydroxyäthy ^ -S-chloraminobenzene, N - ^ - Hydroxyethyl-N - ^ - cyanoathyl-S-chloro-
aminobenzol,
N,N-Di-(^-hydroxyäthyl)-3-acetylamino-amino-aminobenzene,
N, N-Di - (^ - hydroxyethyl) -3-acetylamino-amino-
benzol,
N-ß-Hydroxyäthyl-N-ß-cyanoäthyW-acetyl-benzene,
N-ß-hydroxyethyl-N-ß-cyanoäthyW-acetyl-
araino-aminobenzol,
N,N-Di-(^-hydroxyäthyl)-2-methoxy-5-acetyl-araino-aminobenzene,
N, N-Di - (^ - hydroxyethyl) -2-methoxy-5-acetyl-
amino-aminobenzol,
N-zS-Hydroxyathyl-N-^-cyanoathyl^-methoxy-5-acetylamino-aminobenzol.
amino-aminobenzene,
N-zS-Hydroxyethyl-N - ^ - cyanoathyl ^ -methoxy-5-acetylamino-aminobenzene.
Die erfindungsgemäß erhältlichen Farbstoffe eignen sich, besonders in feinverteilter Form, vorzüglich zum Färben von Gebilden, wie Fasern, Fäden, Flocken, Geweben und Gewirken aus Acetylcellulose [21I2- und Triacetat), linearen Polyestern und Polyamiden.The dyes obtainable according to the invention are particularly suitable, especially in finely divided form, for dyeing structures such as fibers, threads, flakes, woven and knitted fabrics made from acetyl cellulose (2 1 I 2 - and triacetate), linear polyesters and polyamides.
Die erhaltenen Färbungen zeichnen sich durch gute Echtheiten und gutes Ziehvermögen aus. Insbesondere sind die in vielen Fällen ausgezeichneten Naß-, Licht-, Abgas- und thermischen Echtheiten hervorzuheben.The dyeings obtained are distinguished by good fastness properties and good drawability. In particular The wet, light, exhaust gas and thermal fastness properties, which are excellent in many cases, are to be emphasized.
Gegenüber nächstvergleichbaren aus der schweizerischen (339 303), britischen (876 090) und französischen Patentschrift (1 098 546) und den USA.-Patentschriften -2 149 051, 2 980 666 und 3 084 153 bekannten Farbstoffen zeichnen sich die neuen Farbstoffe durch besseres Ziehvermögen auf Polyester und durch bessere Lichtechtheit auf Polyester und 2V2-Acetat aus. Da die bekannten Farbstoffe konstitutionell recht ähnlich den neuen Farbstoffen sind, war es überraschend und nicht vorhersehbar, daß der Substituentenwechsel in der 6-Stellung des Benzthiazolrestes eine so starke Wirkung ausübt.Compared to the closest comparable dyes known from Swiss (339 303), British (876 090) and French patents (1 098 546) and US Patents -2 149 051, 2 980 666 and 3 084 153, the new dyes are characterized by better Drawability on polyester and, thanks to better lightfastness, on polyester and 2V 2 acetate. Since the known dyes are constitutionally quite similar to the new dyes, it was surprising and not foreseeable that the change of substituent in the 6-position of the benzothiazole radical had such a strong effect.
Die in den Beispielen angegebenen Teile sind Gewichtsteile; Prozentangaben beziehen sich auf Gewichtsprozente; Raumteile verhalten sich zu Gewichtsteilen wie das Liter zum Kilogramm unter Normalbedingungen.The parts given in the examples are parts by weight; Percentages relate to Weight percent; Parts of space relate to parts by weight as the liter to the kilogram Normal conditions.
B e i s ρ i e 1 1B e i s ρ i e 1 1
In eine Mischung aus 18 Teilen Nitrosylschwefelsäure mit einem Gehalt von 12,1 % Distickstofftrioxyd und 17 Teilen konzentrierter Schwefelsäure läßt man bei 0 bis 5° C unter Rühren 50 Teile einer Mischung aus wasserfreier Essigsäure und Propionsäure (17:3) einfließen und gibt zu dieser Mischung bei 0 bis 5° C 13,75 Teile 2-Amino-6-carbäthoxybenzthiazol. Anschließend werden weitere 50 Teile der genannten Essigsäure-Propionsäure-Mischung zugesetzt und nach 3 Stunden unter weiterem Rühren bei 0 bis 5° C 2 Teile Harnstoff zugefügt. Die erhaltene klare Diazolösung läßt man bei 0 bis 5° C allmählich zu einer Lösung aus 8,25 Teilen N-Hydroxyäthyl-N-äthylanilin, 25 Teilen Wasser, 6 Teilen konzentrierter Salzsäure und 100 Teilen Eis fließen. Das Reaktionsgemisch wird mit einer Lösung von 60 Teilen Natriumacetat in 300 Teilen Wasser abgestumpft und 12 Stunden gerührt. Der kristalline Farbstoff wird abgesaugt, mit Wasser neutral gewaschen und bei 500C unter vermindertem Druck getrocknet. Der so erhaltene Farbstoff färbt Celluloseacetat in leuchtend rubinroten Tönen von sehr guter Abgasechtheit und Lichtechtheit. 50 parts of a mixture of anhydrous acetic acid and propionic acid (17: 3) are allowed to flow into a mixture of 18 parts of nitrosylsulfuric acid with a content of 12.1% nitrous oxide and 17 parts of concentrated sulfuric acid at 0 to 5 ° C. with stirring Mixture at 0 to 5 ° C 13.75 parts of 2-amino-6-carbethoxybenzthiazole. A further 50 parts of the acetic acid / propionic acid mixture mentioned are then added and, after 3 hours, 2 parts of urea are added at 0 to 5 ° C. with continued stirring. The clear diazo solution obtained is allowed to flow gradually at 0 to 5 ° C. into a solution of 8.25 parts of N-hydroxyethyl-N-ethylaniline, 25 parts of water, 6 parts of concentrated hydrochloric acid and 100 parts of ice. The reaction mixture is truncated with a solution of 60 parts of sodium acetate in 300 parts of water and stirred for 12 hours. The crystalline dye is filtered off with suction, washed neutral with water and dried at 50 ° C. under reduced pressure. The dye obtained in this way dyes cellulose acetate in bright ruby red shades of very good exhaust gas fastness and light fastness.
Verwendet man an Stelle der im Beispiel 1 genannten Kupplungskomponente die in der nachstehenden Tabelle angeführten Azokomponenten, so erhält man Farbstoffe von ähnlich guten Eigenschaften.If the coupling component mentioned in Example 1 is used in the following Azo components listed in the table, dyes with similarly good properties are obtained.
KupplungskomponenteCoupling component
Acetatacetate
Farbton der Färbung aufHue of the staining
Polyamid PolyesterPolyamide polyester
^C2H4CN^ C 2 H 4 CN
o<o <
C2H4O — CH3 C 2 H 4 O - CH 3
Il οIl ο
RotRed
RotRed
RotRed
Rubinruby
RotRed
RotRed
Fortsetzungcontinuation
Acetatfa
acetate
Polyamidshade of color <
polyamide
Polyesteriuf
polyester
C2H4OH \
C 2 H 4 OH
O Il
O
Fortsetzungcontinuation
N
\/
N
\
Polyamidshade of color a
polyamide
Polyester Uf
polyester
\/
\
N
\/
N
\
CH3 Γ
CH 3
N
\/
N
\
N
\/
N
\
CH3 Γ
CH 3
N
\/
N
\
CH3 Γ
CH 3
N
\/
N
\
CH3 Γ
CH 3
N
\/
N
\
\/
\
N
\/
N
\
I 544 363I 544 363
Fortsetzungcontinuation
1010
Polyamidshade of color a
polyamide
Polyester Uf
polyester
ClΓ x
Cl
NHCOCH3 Γ
NHCOCH 3
Ähnliche Farbstoffe werden erhalten, wenn man butoxybenzthiazol diazotiert und mit den in derSimilar dyes are obtained if you diazotized butoxybenzthiazole and with the in the
an Stelle des 2-Amino-6-carboäthoxybenzthiazols das Tabelle angeführten Kupplungskomponenten ver-instead of the 2-amino-6-carboethoxybenzthiazole, the coupling components listed in the table
2 - Amino - 6 - carbomethoxybenzthiazol, 2 - Amino- einigt.2 - amino - 6 - carbomethoxybenzothiazole, 2 - amino unites.
6-carbopropoxybenzthiazol oder 2-Amino-6-carbo- 556-carbopropoxybenzothiazole or 2-amino-6-carbo-55
Claims (1)
O 21. Dyes of the general formula
O 2
Family
ID=
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