DE1644061C3 - Water-insoluble azo dyes of the benzisothiazole series, their production and use for the production of dye preparations - Google Patents
Water-insoluble azo dyes of the benzisothiazole series, their production and use for the production of dye preparationsInfo
- Publication number
- DE1644061C3 DE1644061C3 DE19671644061 DE1644061A DE1644061C3 DE 1644061 C3 DE1644061 C3 DE 1644061C3 DE 19671644061 DE19671644061 DE 19671644061 DE 1644061 A DE1644061 A DE 1644061A DE 1644061 C3 DE1644061 C3 DE 1644061C3
- Authority
- DE
- Germany
- Prior art keywords
- production
- water
- blue
- azo dyes
- dyes
- 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.)
- Expired
Links
- 239000000975 dye Substances 0.000 title claims description 18
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 title claims description 3
- 239000000987 azo dye Substances 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title 2
- -1 propionylamino Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims 3
- 150000008049 diazo compounds Chemical class 0.000 claims 1
- 230000001808 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- LZDSILRDTDCIQT-UHFFFAOYSA-N Dinitrogen trioxide Chemical compound [O-][N+](=O)N=O LZDSILRDTDCIQT-UHFFFAOYSA-N 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 240000000358 Viola adunca Species 0.000 description 3
- 235000005811 Viola adunca Nutrition 0.000 description 3
- 235000013487 Viola odorata Nutrition 0.000 description 3
- 235000002254 Viola papilionacea Nutrition 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QPKOBORKPHRBPS-UHFFFAOYSA-N Bis(2-Hydroxyethyl) terephthalate Chemical compound OCCOC(=O)C1=CC=C(C(=O)OCCO)C=C1 QPKOBORKPHRBPS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VQTGUFBGYOIUFS-UHFFFAOYSA-N Nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- SQBCSDZTDXLTLE-UHFFFAOYSA-N 5-nitro-2,1-benzothiazol-3-amine Chemical compound C1=CC([N+]([O-])=O)=CC2=C(N)SN=C21 SQBCSDZTDXLTLE-UHFFFAOYSA-N 0.000 description 1
- 229960000583 Acetic Acid Drugs 0.000 description 1
- 241000272201 Columbiformes Species 0.000 description 1
- 241001366278 Leptotes marina Species 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011528 polyamide (building material) Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000010981 turquoise Substances 0.000 description 1
Description
mit einer Kupplungskomponente der Formelwith a coupling component of the formula
™»-γ-Ο™ »- γ -Ο
Methyl, Chlor, Acetylamino oder Propionylamino, η: oder 2, Y eine direkte Bindung oder Sauerstoff und F Wasserstoff, Alkyl mit 1 bis 4 C-Atomen, jS-Hydroxyal kyl mit 2 oder 3 C-Atomen, /J.y-Dihydroxypropyl /J-Hydroxy-y-chlorpropyl, Methoxy- oder Äthoxyäthy] Acetoxyäthyl, Carbomethoxy- oder Carboäthoxyäthyl Cyanäthyl Chloräthyl, 0-AcetyIaminoäthyl oder y-Ace tylaminopropyl bedeuten.Methyl, chlorine, acetylamino or propionylamino, η : or 2, Y a direct bond or oxygen and F hydrogen, alkyl with 1 to 4 carbon atoms, jS-hydroxyalkyl with 2 or 3 carbon atoms, / jy-dihydroxypropyl / J -Hydroxy-y-chloropropyl, methoxy or ethoxyethyl] acetoxyethyl, carbomethoxy or carboethoxyethyl cyanoethyl, chloroethyl, 0-acetylaminoethyl or γ-acetylaminopropyl mean.
Man erhält diese Farbstoffe, wenn man Diazoverbin düngen von Aminen der allgemeinen Formel IIThese dyes are obtained by using Diazoverbin fertilize amines of the general formula II
fürfor
umsetzt, A, n, R, Y und Z haben dabei die Anspruch 1 angegebenen Bedeutungen.converts, A, n, R, Y and Z have the meanings given in claim 1.
3. Farbstoffzubereitungen zum Färben von synthetischen Fasern enthaltend neben üblichen Be- standteilen Farbstoffe gemäß Anspruch 1.3. Dye preparations for dyeing synthetic fibers containing, in addition to the usual constituent dyes according to claim 1.
Diese Erfindung betrifft Farbstoffe der allgemeinen Formel 1 AThis invention relates to dyes of general formula 1 A.
5555
NH,NH,
3535 mit Kupplungskomponenten der allgemeinen For mel IIIwith coupling components of the general For mel III
4040
4545
in der A Wasserstoff. Chlor oder Brom, Z Wasserstoff,in the A hydrogen. Chlorine or bromine, Z hydrogen, (III)(III)
umsetzt, wobei A, n, R, Y und Z die angegebene) Bedeutungen haben.converts, where A, n, R, Y and Z have the meanings given).
Für Z seien Wasserstoff, Methyl-, Chlor, Acetylamin« oder Propionylamino genanntLet Z be hydrogen, methyl-, chlorine, acetylamine « or called propionylamino
Als Reste R kommen Reste wie Methyl, Äthyl, Propy Butyl, /J-Hydroxyäthyl, j3-Methoxy- oder -Äthoxyäthy jJ-Cyanäthyl, 0-Chloräthyl, Jj-Acetoxyäthyl, /Ϊ-Carbo methoxy- oder -äthoxyäthyl, j3-Hydroxypropyl, j?,y-Di hydroxypropyl, 0-Acetylaminoäthyl oder y-Acetylami nopropyl in Betracht.The radicals R are radicals such as methyl, ethyl, propy butyl, / I-hydroxyethyl, j3-methoxy or ethoxyethy jJ-cyanoethyl, 0-chloroethyl, Jj-acetoxyethyl, / Ϊ-carbo methoxy or ethoxyethyl, j3-hydroxypropyl, j?, y-di hydroxypropyl, 0-acetylaminoethyl or γ-acetylami nopropyl into consideration.
Verbindungen der Formel II sind z. B.: 3-Amino-5-ni tro-2,1 -benz-isothiazol, 3-Amino-5-nitro-7-chlor-2,l benz-isothiazol oder 3-Amino-5-nitro-7-brom-2,l-benz isothiazol.Compounds of formula II are, for. E.g .: 3-amino-5-nitro-2,1-benz-isothiazole, 3-amino-5-nitro-7-chloro-2, l benz-isothiazole or 3-amino-5-nitro-7-bromo-2, l-benz isothiazole.
CH,CH,
CH5-CH,CH 5 -CH,
^CH2-CH3 ^ CH 2 -CH 3
'CH2- CH2- Ο—ζ~\ CH2-CH2-CH2-CH3 'CH 2 - CH 2 - Ο— ζ ~ \ CH 2 -CH 2 -CH 2 -CH 3
CH2-CH2-CH 2 -CH 2 -
CH2-CH2-OHCH 2 -CH 2 -OH
CH2-CH2-O CH2 CH3 CH 2 -CH 2 -O CH 2 CH 3
CH2-CH2-CH3 CH 2 -CH 2 -CH 3
CH2-CH2-O CH2-CH2-OHCH 2 -CH 2 -O CH 2 -CH 2 -OH
IlIl
/CH2-CH2-O-C-CH3 / CH 2 -CH 2 -OC-CH 3
CH.-C^-O^^) CH2-CH2-OCH3 CH.-C ^ -O ^^) CH 2 -CH 2 -OCH 3
CH2 CH2 NX λ, CH 2 CH 2 NX λ,
ίοίο
2020th
4040
4545
5555
6ο6ο
CH2-CH2-CNCH 2 -CH 2 -CN
ν^Ν-ν ^ Ν -
CH2-CH,-Ο—\ CH2-CH2-OCH3 CH 2 -CH, -Ο- \ CH 2 -CH 2 -OCH 3
-N-N
CH2 4CH 2 4
<ν^Ν <ν ^ Ν
IlIl
CH2-CH2-C-OCH3 KCH2-CH2-O-^\CH 2 -CH 2 -C-OCH 3 K CH 2 -CH 2 -O - ^ \
/CH2—CH2-OH 35 V_/^~N / CH 2 -CH 2 -OH 35 V _ / ^ ~ N
IlIl
CH2-CH2-O-C-CH 2 -CH 2 -OC-
CH2-CH2
CH2-CH2 CH 2 -CH 2
CH 2 -CH 2
CH3 CH 3
CH3CH3
i^-N i ^ - N
CH2-CH 2 -
CH2-CH2-OHCH 2 -CH 2 -OH
CHj-CHi-^^CHj-CHi - ^^
CH2-CH2-CNCH 2 -CH 2 -CN
CH2 CH2 >x x, OCH 2 CH 2 > x x, O
IlIl
CH2—CH2 O C CH3 CH 2 -CH 2 OC CH 3
Il CH2-CH2-C-OCH3 II CH 2 -CH 2 -C-OCH 3
CH1-CH1^fCH 1 -CH 1 ^ f
J? CH3 J? CH 3
CH2-CH2-OCH3 CH 2 -CH 2 -OCH 3
—CHr-—CH r -
-N-N
CH2-CH2-C-OC2HCH 2 -CH 2 -C-OC 2 H
■2■ 2
CH2 CH2 <ix OCH 2 CH 2 <ix O
IlIl
CH2-CH2-C-OCH3 CH 2 -CH 2 -C-OCH 3
CH3 CH 3
C-H2 (-Ή2 CC-H2 (-Ή2 C
CH2-CH2-CNCH 2 -CH 2 -CN
CH3 CH 3
CH2-CH2-^CH 2 -CH 2 - ^
CH2-CH2-CH2-NH-C-CH3 CH 2 -CH 2 -CH 2 -NH-C-CH 3
4040
4545
CH2-CH2-CNCH 2 -CH 2 -CN
CH3 CH 3
O CH2-CH2-CH2-NH-C-CH3 O CH 2 -CH 2 -CH 2 -NH-C-CH 3
-N-N
CH3 ( CH 3 (
6ο6ο
2 CH2 OH2 CH2 OH
OHOH
CH2-CH-CH2- OHCH 2 -CH-CH 2 - OH
IlIl
CH2-CH2-CH2-NH -C-CH3 CH 2 -CH 2 -CH 2 -NH -C-CH 3
Jh3 3rd century
oh ch2-ch-ch2-cioh ch 2 -ch-ch 2 -ci
CH,-CH,-OHCH, -CH, -OH
γ/γ /
CH3 CH 3
OH CH2-CH-CH2-ClOH CH 2 -CH-CH 2 -Cl
Cli^\__/ OH Cli ^ \ __ / OH
CH2-CH-CH2-OHCH 2 -CH-CH 2 -OH
CH2-CH2-OHCH 2 -CH 2 -OH
OH CH2-CH-CH2-ClOH CH 2 -CH-CH 2 -Cl
CH2-CH2-CNCH 2 -CH 2 -CN
CH9 C-H-CH9 C-H-
CH2-CH2-CH2-N-C-CH3 NCH 2 -CH 2 -CH 2 -NC-CH 3 N
CH,-CH,-O-CH, -CH, -O-
CH2-CH2-OCH3 CH 2 -CH 2 -OCH 3
CH2-CH2-/)CH 2 -CH 2 - /)
CH2-CH2-N-C-CH3 CH 2 -CH 2 -NC-CH 3
CH2 CH2 <^CH 2 CH 2 <^
v,ri2 LrIiv, ri2 LrIi
CH2-CH2-O-^ CH2-CH2-CNCH 2 -CH 2 -O- ^ CH 2 -CH 2 -CN
CH2-CH2-CNCH 2 -CH 2 -CN
NHCOCH3 NHCOCH 3
CH2-CH2-^CH 2 -CH 2 - ^
CH2-CH2-OHCH 2 -CH 2 -OH
CH2 —CH2 C OCH3 CH 2 - CH 2 C OCH 3
CH2-CH2-CH 2 -CH 2 -
CH2-CH2-OHCH 2 -CH 2 -OH
CH2-CH2-O^2^
CH,-CH,-OH CH 2 -CH 2 -O ^ 2 ^
CH, -CH, -OH
NHCOCH3 NHCOCH 3
CH2-CH2-O-C-CH3 CH 2 -CH 2 -OC-CH 3
CH7-CH-CH 7 -CH-
NHCOCH3 NHCOCH 3
Die Farbstoffe dieser Erfindung eignen sich, besonders in feinverteilter Form, insbesondere zum Färben von Gebilden, wie Fasern, Flocken, Fäden, Geweben oder Gewirken aus linearen Polyestern, wie Polyäthylenglykolterephthalat Celluloseester, wie 2V2- oder 3-Acetat oder Polyamide sowie Mischungen der genannten Fasern mit anderen kann man ebenfalls damit färben. Die erfindungsgemäß erhältlichen Farbstoffe zeichnen sich durch gutes Ziehvermögen und die damit hergestellten Färbungen durch gute Echtheiten aus. Insbesondere sind die in vielen Fällen ausgezeichne ten Naß- und thermischen Echtheiten hervorzuheben. The dyes of this invention are suitable, especially in finely divided form, in particular for dyeing structures such as fibers, flakes, threads, woven or knitted fabrics made from linear polyesters such as polyethylene glycol terephthalate cellulose esters such as 2V2 or 3 acetate or polyamides and mixtures of the fibers mentioned you can also use it to color with others. The dyes obtainable according to the invention are distinguished by good drawability and the dyeings produced with them have good fastness properties. In particular, the wet and thermal fastness properties , which are excellent in many cases, should be emphasized.
Gegenüber nächst vergleichbaren, aus den belgischen Patentschriften 6 71 262 und 6 82 396 und den britischen Patentschriften 8 94 012 und 8 96 232 bekannten Farb stoffen haben die erfindungsgemäßen Farbstoffe Vor teile in der Lichtechtheit auf Polyester sowie im Ziehvermögen auf 2'/2-Acetat und in der Schweißechtheit auf Polyamid. Compared to the next comparable, from Belgian patents 6 71 262 and 6 82 396 and British patents 8 94 012 and 8 96 232 known dyes, the dyes according to the invention have advantages in the lightfastness on polyester and in the drawability on 2 '/ 2 acetate and in the fastness to perspiration on polyamide.
Es handelt sich bei den erfindungsgemäßen Farbstoffen um eine enge nicht naheliegende Auswahl, mit der esThe dyes according to the invention are a narrow, non-obvious selection with which it is möglich ist blaue Nuancen zu erzielen, die mit Azofarbstoffen kaum zugänglich sind.it is possible to achieve blue nuances that are hardly accessible with azo dyes.
Die Angaben über Teile und Prozente in den nachfolgenden Beispielen beziehen sich auf das GewichtThe data on parts and percentages in the following examples relate to the Weight
B e i s ρ i e 1 1 B ice ρ i e 1 1
9,75 Teile S-Amino-S-nitro^l-benzisothiazol werden bei 10 bis 15°C in 100 Teile 85prozentiger Schwefelsäure eingetragen. Zu der erhaltenen Lösung läßt man bei 09.75 parts of S-amino-S-nitro ^ l-benzisothiazole are entered at 10 to 15 ° C in 100 parts of 85 percent sulfuric acid. The solution obtained is left at 0 bis 5°C 15 Teile Nitrosylschwefelsäure (mit einem Gehalt von 123% an freiem Distickstofftrioxid) eintropfen. Man rührt die entstandene, klare Diazolösung 3 Stunden bei 0 bis 5° C und läßt dann bei dieser Temperatur eine Lösung von 12,75 Teilen N-0-Oxäthyl-Up to 5 ° C 15 parts of nitrosylsulfuric acid (with a Content of 123% of free dinitrogen trioxide) drop in. The resulting, clear diazo solution is stirred for 3 hours at 0 to 5 ° C. and then left at this Temperature a solution of 12.75 parts of N-0-Oxäthyl- N-0-phenyläthyl-metatoluidin in 50 Teilen Eisessig zufließen, rfihrt 30 Minuten nach und trägt die Lösung in 1500 Teile Eis und Wasser ein. Der kristalline ausgefallene Farbstoff wird nach 6stündigem Rühren abgesaugt mit Wasser gewaschen und bei 500C unterN-0-phenylethyl-metatoluidine in 50 parts of glacial acetic acid flow in, stir for 30 minutes and add the solution to 1500 parts of ice and water. The crystalline dyestuff which has precipitated out is filtered off with suction after stirring for 6 hours with water and washed at 50 ° C. under
6s vermindertem Druck getrocknet Der so erhaltene Farbstoff färbt Polyäthylenglykoltherephthalat in blauen Tönen mit sehr guten NaB- und thermischen EchtheitseigenschafteaThe resultant dried under reduced pressure for 6 s Dye colors polyethylene glycol therephthalate in blue tones with very good NaB and thermal properties Authenticity properties a
709609/38709609/38
1010
Kupplungskomponenten die in der folgenden Tabelle Beispiel Kupplungskomponente aufgeführten Komponenten, so erhält man Farbstoffe Nr· von ähnlichen Eigenschaften. Coupling components The components listed in the following table, Example Coupling Components, result in dyes No. having similar properties.
CH4-CNCH 4 -CN
CH,CH,
marineblau navy blue
C2H4 O C CH3C 2 H 4 OC CH 3
1212th
blaublue
IlIl
C2H4-O-C-CH3 C 2 H 4 -OC-CH 3
1313th
blaublue
CH3 CH 3
C2H4CO2-C2H5 C 2 H 4 CO 2 -C 2 H 5
1414th
marine- =v blaunavy = v blue
blaublue
1515th
C2H4-OHC 2 H 4 -OH
ClCl
blauviolett blue-violet
-N-N
C2H4^y^C 2 H 4 ^ y ^
C2H4-OHC 2 H 4 -OH
4545
5050
4 >-N4> -N
manneblauman blue
C2H4-OHC 2 H 4 -OH
CH2-C2H4-CNCH 2 -C 2 H 4 -CN
CH,CH,
1717th
marineblaunavy blue
violettviolet
Farbtonhue
derthe
Färbungcoloring
aufon
Polyesterpolyester
C2H4-O-C-CH3 C 2 H 4 -OC-CH 3
blauviolett blue-violet
blaumarine
blue
HO
H
—0—C-CH3 Il
-0-C-CH 3
violettblue
violet
VCH2—CH-CH2
OH OH V CH 2 -CH-CH 2
OH OH
manneblau man blue
manneblau man blue
2—CH-CH2
OH OH2-CH-CH 2
OH OH
C2H4-C 2 H 4 -
CH2-CH-CH2-ClCH 2 -CH-CH 2 -Cl
OH C2H4-OCH3 OH C 2 H 4 -OCH 3
C2H4-C 2 H 4 -
marineblaunavy blue
marineblaunavy blue
^C2H4-OH ^C2H4-^ C 2 H 4 -OH ^ C 2 H 4 -
türkisturquoise
I NHCOCH3 I NHCOCH 3
13,7 g 3-Amino-5-nitro-7-brom-2,l-benziso thiazol werden bei 10 bis 150C in 120 Teilen konzentrierter Schwefelsäure gelöst Zu dieser Lösung läßt man bei 0 bis 5°C zunächst 50 Teile eines Eisessig-Propiomsäure-Gemisches (17 :3) eintropfen und diazotiert dann bei dieser Temperatur durch allmähliche Zugabe von 15 Teilen Nitrosylschwefelsäure (mit einem Gehalt von 12,8% freiem Distickstofftrioxid). Nach dreistündigem Rühren wird die erhaltene klare Diazolösung allmählich in eine Lösung von 14,85 Teilen N-/?-Acetoxyäthyl-N-j3-phenyl-äthyl-meta-toluidin, 250 Teilen Aceton, 10 Teilen konzentrierter Salzsäure und 75 Teilen Eis einfließen gelassen. Nach weiteren 30 Minuten werden 1000 Teile Eis und Wasser zugesetzt; der kristallin anfallende Farbstoff wird abgesaugt, nachgewaschen und bei 5O0C unter vermindertem Druck getrocknet. Auf Polyäthylenglykolterephthalat ergibt dieser Farbstoff eine taubenblaue Färbung mit sehr guten thermischen Echtheitseigenschaften. Verwendet man an Stelle des N-jJ-Acetoxyathyl-N-jS-phenylathyl-meta-toluidins die in der voranstehenden Tabelle angeführten Kupplungskomponenten und verfährt wie im Beispiel 19 beschrieben, so erhält man Farbstoffe, die gegenüber den entsprechenden mit 3-Amino-5-nitro-2,l-benzisothiazol als Diazokomponente hergestellten Farbstoffen im Farbton bathochrom verschoben sind.13.7 g of 3-amino-5-nitro-7-bromo-2, l-benziso thiazole are dissolved at 10 to 15 0 C concentrated sulfuric acid in 120 parts To this solution is allowed to at 0 to 5 ° C initially 50 parts of Glacial acetic acid-propiomic acid mixture (17: 3) is added dropwise and then diazotized at this temperature by the gradual addition of 15 parts of nitrosylsulfuric acid (with a content of 12.8% free dinitrogen trioxide). After three hours of stirring, the clear diazo solution obtained is gradually poured into a solution of 14.85 parts of N - /? - acetoxyethyl-N-j3-phenyl-ethyl-meta-toluidine, 250 parts of acetone, 10 parts of concentrated hydrochloric acid and 75 parts of ice . After a further 30 minutes, 1000 parts of ice and water are added; the resulting crystalline dye is suction filtered, washed and dried at 5O 0 C under reduced pressure. On polyethylene glycol terephthalate, this dye gives a pigeon blue coloration with very good thermal fastness properties. If the coupling components listed in the table above are used in place of the N-jJ-acetoxyethyl-N-jS-phenylethyl-meta-toluidine and the procedure is as described in Example 19, dyes are obtained which have 3-amino-5 -nitro-2, l-benzisothiazole as diazo component produced dyes are shifted bathochromically in hue.
Claims (2)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US731621A US3573273A (en) | 1967-06-03 | 1968-05-23 | Water-insoluble monoazo dyes containing 3-amino-2,1-benzisothiazole coupled to an n,n-disubstituted aniline |
| FR1568501D FR1568501A (en) | 1967-06-03 | 1968-05-29 | |
| CH799368A CH494260A (en) | 1967-06-03 | 1968-05-30 | Process for the preparation of water-insoluble azo dyes of the benzisothiazole series |
| GB26204/68A GB1217714A (en) | 1967-06-03 | 1968-05-31 | New water insoluble azo dyes of the benzisothiazole series |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0092855 | 1967-06-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1644061C3 true DE1644061C3 (en) | 1977-03-03 |
Family
ID=
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