DE1644181C3 - Monoazo dyes - Google Patents
Monoazo dyesInfo
- Publication number
- DE1644181C3 DE1644181C3 DE19661644181 DE1644181A DE1644181C3 DE 1644181 C3 DE1644181 C3 DE 1644181C3 DE 19661644181 DE19661644181 DE 19661644181 DE 1644181 A DE1644181 A DE 1644181A DE 1644181 C3 DE1644181 C3 DE 1644181C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- dyes
- monoazo dyes
- mol
- parts
- 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 15
- 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 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000000987 azo dye Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 125000000542 sulfonic acid group Chemical group 0.000 description 4
- -1 4 - nitro - 2 - chloro - 2 - cyananiline Chemical compound 0.000 description 3
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KWMDHCLJYMVBNS-UHFFFAOYSA-N 2-bromo-4,6-dinitroaniline Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1[N+]([O-])=O KWMDHCLJYMVBNS-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 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
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 1
- IPMNLGOBXWTQRV-UHFFFAOYSA-N 4-aminobenzene-1,3-dicarbonitrile Chemical compound NC1=CC=C(C#N)C=C1C#N IPMNLGOBXWTQRV-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 229910004013 NO 2 Inorganic materials 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N para-methylaniline Natural products CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Description
NHAc Ri NHAc Ri
worin R ein von Sulfonsäuregruppen freier Rest der Benzolreihe, Ac eine Formyl- oder Acetylgruppe, R1 ein gegebenenfalls durch C1-C4-AIlCyI, Chlor, Brom, Q-Q-Alkoxy, Acetylamino oder CF3 substituierter Phenylrest und R2 und R3 Wasserstoff oder die Gruppe CrC5-Alkylen-X sind, wobei X Wasserstoff, OH oder CN istwherein R is a radical of the benzene series free of sulfonic acid groups, Ac is a formyl or acetyl group, R 1 is a phenyl radical optionally substituted by C 1 -C 4 -AlCyI, chlorine, bromine, QQ-alkoxy, acetylamino or CF 3, and R 2 and R 3 Are hydrogen or the group CrC 5 -alkylene-X, where X is hydrogen, OH or CN
Für die Herstellung der erfinduugsgemäßen Azofarbstoffe geeignete Diazokomponenten smd bali« 4 - Nitroanüin, 4 - Nitro - 2 - chlor- - 2 - cyananilin, 2,4 - Dicyananilin. 3 - Chlor - 4 - cyananiiin, 2-Cyan-Diazo components suitable for the preparation of the azo dyes according to the invention are bali «4 - nitroaniline, 4 - nitro - 2 - chloro - 2 - cyananiline, 2,4 - dicyananiline. 3 - chlorine - 4 - cyananiiin, 2-cyano-
■ n:«.«n<inil:n ? S - Oirvananilin■ n: «.« N <inil: n? S - orirvananiline
2020th
25 ^Dinitranilin, 3-Oüor-4-cyananihn, 2-Cyan- \hinraiiüin. 3 4 - DicyananUin, U> - Dicyananihn, I6 DicS^4-'nitrA 2 - Chlor - 4 - cyananilin, A- Amino - acetophenon, 2 - Amino - 5 - nrtroto uo^ 2 Amino - 5 - nitroanisol 3 - Nitro - 4 - aminotoluol, 2,4 Soraniün, 2,5-Dichlor-4-nurar '·η, 2-Tnithl-4-chloranilin, 3-Chlor-4-ar .o-l-nbenzol 2 - Cyan - 4,5,6 - U^oloran.hn, -6-bromanUin, ^-Cyan-^-diritraiuhn, fCyan-o-brom- oder ^-chlor-4-mtranihn, 2,4- D,-cyany. 6 - chloranilin, 2 - Methoxy - 4 - nitran.hn, SAmino-S-nitro-benzoesäureraethylester, 4-Ammobenzoesäurealkylamide, wie -methyl- oder -dimethyl-S^ Sobenzoesäuremethylester, 3 - Njtroraminobenzoesäurebutylester 1 - Ammobenzol - 3-oder-4-methylsulfonoder-äthybulfon. 25 ^ Dinitranilin, 3-Oüor-4-cyananihn, 2-Cyan- \ hinraiiüin. 3 4 - DicyananUin, U> - Dicyananihn, I 6 DicS ^ 4-'nitrA 2 - chlorine - 4 - cyananiline, A - amino - acetophenon, 2 - amino - 5 - nrtroto uo ^ 2 amino - 5 - nitroanisole 3 - nitro - 4 - aminotoluene, 2,4 Soraniün, 2,5-dichloro-4- n URAR '· η, 2-Tnithl-4-chloroaniline, 3-chloro-4- r a .OL-nbenzol 2 - cyano - 4, 5,6 - U ^ oloran.hn, -6-bromanUin, ^ -Cyan - ^ - diritraiuhn, fCyan-o-bromo- or ^ -chlor-4-mtranihn, 2,4- D, -cyan y . 6 - chloraniline, 2 - methoxy - 4 - nitran.hn, SAmino-S-nitro-benzoic acid ethyl ester, 4-ammobenzoic acid alkylamides, such as -methyl- or -dimethyl-S ^ sobenzoic acid methyl ester, 3 - nitroraminobenzoic acid butyl ester 1 - ammobenzene - 3- or 3- -methylsulphone or -ethybulphone.
Für die Herstelhing der erfindungsgemaßen Azofarbstoffe geeignete Kupplungskomponenten smd beispielsweise die folgenden:Coupling components suitable for the preparation of the azo dyes according to the invention are, for example the following:
Gegenstand der Erfindung sind sulfonsäuregruppenfreie Monoazofarbstoffe der allgemeinen FormelThe invention relates to monoazo dyes of the general formula which are free from sulfonic acid groups
(D(D
NHAcNHAc
3535
worin R ein von Sulfonsäuregruppen freier Rest der Benzolreihe, Ac eine Formyl- oder Acetylgruppe, R1 ein gegebenenfalls durch C1-C4-AUCyI, Chlor, Brom, C1-C4-Alkoxy, Acetylamino oder CF3 substituierter Phenylrest und R2 und R3 Wasserstoff oder die Gruppe Q-Cs-Alkylen-X sind, wobei X Wasserstoff, OH oder CN istwherein R is a radical of the benzene series free of sulfonic acid groups, Ac is a formyl or acetyl group, R 1 is a phenyl radical optionally substituted by C 1 -C 4 -AUCyI, chlorine, bromine, C 1 -C 4 -alkoxy, acetylamino or CF 3, and R 2 and R 3 are hydrogen or the group Q-Cs-alkylene-X, where X is hydrogen, OH or CN
Man erhält diese wertvollen Monoazofarbstoffe, wenn man eine benzolische Diazokomponente mit einem Amin der allgemeinen FormelThese valuable monoazo dyes are obtained if one has a benzene diazo component an amine of the general formula
(H)(H)
4040
4545
NHAcNHAc
in der NH Acyl, R1, R2 und R3 die oben angegebene Bedeutung besitzen, in p-Stellung zur Gruppein which NH acyl, R 1 , R 2 and R 3 have the meaning given above, in the p-position to the group
— N- N
6060
kuppelt und dabei die Ausgangskomponenten frei von Sulfonsäuregruppen wählt.couples and thereby chooses the starting components free of sulfonic acid groups.
Die Kupplung der Ausgangskomponenten erfolgt in üblicher Weise in vorzugsweise saurer Lösung öder Suspension.The starting components are coupled in the customary manner, preferably in an acidic solution desolate suspension.
CH2CH2OHCH 2 CH 2 OH
NHCOCH3 NHCOCH 3
9 CH2CH2OH9 CH 2 CH 2 OH
CH2CH2OHCH 2 CH 2 OH
CH2OHCH 2 OH
NHCOCH3 NHCOCH 3
j
NHCOCH3 j
NHCOCH 3
NHCOCH,NHCOCH,
CH,CH,
NHCOCH3 NHCOCH 3
Aus der Gruppe der erfindungsgemäßen Azofarbstoffe sind solche der allgemeinen FormelFrom the group of the azo dyes according to the invention there are those of the general formula
5555
NHAcNHAc
besonders bevorzugt; hierin besitzen Ac, R1, R2 und R3 die oben angegebene Bedeutung. R? steht für Cl, 65 Sr oder CN, R6 und R7 stehen für gleiche oder verschiedene Reste Wasserstoff, NO2, Cl, Br, CN, CH3 oder OCH3.particularly preferred; Here Ac, R 1 , R 2 and R 3 have the meaning given above. R ? stands for Cl, 65 Sr or CN, R 6 and R 7 stand for identical or different radicals hydrogen, NO 2 , Cl, Br, CN, CH 3 or OCH 3 .
Kupplungskomponenten der allgemeinen FormelCoupling components of the general formula
R2 R 2
(II)(II)
NHAcNHAc
3535
4040
45 lassen sich nach folgendem Verfahren herstellen: 45 can be produced using the following process:
2,4-Oinitrochlorbenzol wird in wäßrig alkalischem Medium bei Temperaturen von etwa 10O0C mit Phenolaten zu 2,4-Dinitrodiphenyläthern umgesetzt, die anschließend mit Zinn(II)-chlorid zu 2-Amino-4-nitrodiphenyläthern reduziert, mit Alkylierungsmitteln wie Toluolsulfonsäureestern oder Alkylhalogeniden mono- oder dialkyliert und nach katalytischer Reduktion der Nitrogruppe mit Raney-Nickel in üblicher Weise mit Säurechloriden oder Säureanhydriden acylicrt werden.2,4-Oinitrochlorbenzol is reacted in an aqueous alkaline medium at temperatures of about 10O 0 C and 2,4-phenolates to Dinitrodiphenyläthern that reduces then nitrodiphenyläthern-2-amino-4 with tin (II) chloride to, with alkylating agents such as toluenesulfonic or alkyl halides are mono- or dialkylated and, after catalytic reduction of the nitro group with Raney nickel, are acylated in the usual manner with acid chlorides or acid anhydrides.
Ein weiteres Verfahren zur Herstellung derartiger Kupplungskomponenten ist in der deutschen Patentschrift 1 543 625 beschrieben.Another method for producing such coupling components is described in the German patent 1 543 625.
Die erfindungsgemäßen Farbstoffe eignen sich vorzüglich zum Färben und Bedrucken hydrophober Materialien, insbesondere von Textilien oder Fasern aus aromatischen Polyestern, z. B. von Polyäthylenterephthalaten oder von Kondensationsprodukten aus Terephthalsäure und l,4-Bis-(hydroxymethyl)-cyclnhexan. Man erhält auf diesen Materialien Färbungen und Drucke mit sehr guten Echtheitseigenschaften. The dyes according to the invention are particularly suitable for dyeing and printing more hydrophobic Materials, especially of textiles or fibers made of aromatic polyesters, e.g. B. of polyethylene terephthalates or of condensation products from terephthalic acid and 1,4-bis (hydroxymethyl) -cyclnhexane. Dyeings and prints with very good fastness properties are obtained on these materials.
Die Farbstoffe eignen sich auch zum Färben und Bedrucken von Celluloseacetat und Triacetylcellulose und von synthetischem Polyamid- und Polyacrylnitrilfasermaterial. The dyes are also suitable for dyeing and printing cellulose acetate and triacetyl cellulose and of synthetic polyamide and polyacrylonitrile fiber material.
Gegenüber dem Farbstoff des Beispiels 1 der belgischen Patentschrift 643 774 sowie gegenüber dem Farbstoff des Beispiels 8 der USA-Patentschrift 2 204607 zeigen nächstvergleichbare erfindungsgemäße Farbstoffe den Vorteil der besseren Sublimiercchtheit auf Polyester.Compared to the dye of Example 1 of Belgian Patent 643 774 and compared to the Dyes of Example 8 of US Pat. No. 2,204607 show next comparable according to the invention Dyes have the advantage of better sublimation fastness on polyester.
Die in den Beispielen angegebenen Teile beziehen sich auf Gewichtsteile.The parts given in the examples relate to parts by weight.
26,2 Teile (1Z10 Mol) 2,4-Dinitro-6-bromanilin werden feingepulvert und mit 200 ml Eisessig angerührt. Unter Kühlung auf 13 bis 14°C wird mit 15 ml Nitrosylschwefelsäure, 0,11 Mol salpetrige Säure enthaltend, diazotiert. Nach 30 Minuten wird überschüssige salpetrige Säure durch Zugabe von fester Amidosulfonsäure zerstört. Die Diazolösung läßt man unter Rühren zu einer Lösung von 27 Teilen (1Z10 Mol) 2 - Dimethylamino - 4 - acetamido - diphenylether in 100 ml Eisessig und 11 Eiswasser einfließen. Der sich sofort abscheidende blaue kristalline Azofarbstoff wird abgesaugt, auf der Nutsche mit Wasser gewaschen und anschließend getrocknet. Zur Reinigung kann er aus Dimethylformamid umkristallisiert werden. Der Farbstoff färbt Polyesterfasern in klaren blauen Farbtönen mit guten Echtheitseigenschaften.26.2 parts ( 1 Z 10 mol) of 2,4-dinitro-6-bromaniline are finely powdered and mixed with 200 ml of glacial acetic acid. While cooling to 13 ° to 14 ° C., 15 ml of nitrosylsulfuric acid containing 0.11 mol of nitrous acid are diazotized. After 30 minutes, excess nitrous acid is destroyed by adding solid sulfamic acid. The diazo solution is allowed to flow into a solution of 27 parts ( 1 Z 10 mol) of 2-dimethylamino-4-acetamido-diphenyl ether in 100 ml of glacial acetic acid and 1 liter of ice water, with stirring. The blue crystalline azo dye which separates out immediately is filtered off with suction, washed with water on the suction filter and then dried. For purification, it can be recrystallized from dimethylformamide. The dye dyes polyester fibers in clear blue shades with good fastness properties.
52,4 Teile (0,2MoI) 2,4-Dinitro-6-bromanilin werden wie im Beispiel 1 beschrieben mit Nitrosyl· schwefelsäure in Eisessig diazotiert. Die Diazolösung wird mater Rühren in eine Lösung von 66 Teilen (0,2 Mol) 2 - (Di - β - oxyäthyl)amino - 4 - acetylamino-52.4 parts (0.2 mol) of 2,4-dinitro-6-bromaniline are diazotized with nitrosylsulfuric acid in glacial acetic acid as described in Example 1. The diazo solution is stirred into a solution of 66 parts (0.2 mol) of 2 - (di - β - oxyethyl) amino - 4 - acetylamino-
diphenylether in 400 ml Eisessig und 11 Eiswasser eingetropft Der sich spontan abscheidende blaue Azofarbstoff wird durch Absaugen isoliert, gut mit Wasser gewaschen und getrocknet. Der Farbstoff färbt Polyesterfasern in klaren blauen Tönen mit S guten Echtheitseigenschaften.diphenyl ether in 400 ml of glacial acetic acid and 11 ice water dropped in The spontaneously separating blue azo dye is isolated by suction, well with Water washed and dried. The dye dyes polyester fibers in clear blue tones with an S good fastness properties.
26,2 Teile (0,1 Mol) 2,4-Dinitro-6-bromaniün werden wie im Beispiel 1 beschrieben in Eisessig mit w NitrosylschwefeJsäure diazotiert. Die Diazolösung läßt man unter Rühren langsam in eine Lösung von 30 Teilen (0,1 Mol) 2 - (N - Methyl - N - /i - oxäthyf)-aniinc-4-acetylamino-diphenyläther in 400 ml Eisessig und 11 Eiswasser einfließen. Der sich sofort kristallin abscheidende blaue Azofarbstoff wird durch Absaugen isoliert, gut mit Wasser gewaschen und getrocknet Der Farbstoff färbt Polyesterfasern in klaren blauen Tönen mit guten Echtheitseigenschaften.26.2 parts (0.1 mol) of 2,4-dinitro-6-bromaniün are diazotized as described in Example 1 in glacial acetic acid with w nitrosylsulfuric acid. The diazo solution is allowed to slowly flow into a solution of 30 parts (0.1 mol) of 2 - (N - methyl - N - / i - oxäthyf) aniineinc-4-acetylamino-diphenyl ether in 400 ml of glacial acetic acid and 1 liter of ice water, while stirring. The blue azo dye, which separates out immediately in crystalline form, is isolated by suction, washed well with water and dried. The dye dyes polyester fibers in clear blue shades with good fastness properties.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0050723 | 1966-11-22 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1644181A1 DE1644181A1 (en) | 1971-07-15 |
| DE1644181B2 DE1644181B2 (en) | 1974-06-27 |
| DE1644181C3 true DE1644181C3 (en) | 1975-02-20 |
Family
ID=7104018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661644181 Expired DE1644181C3 (en) | 1966-11-22 | 1966-11-22 | Monoazo dyes |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE706921A (en) |
| CH (3) | CH1778867A4 (en) |
| DE (1) | DE1644181C3 (en) |
| GB (1) | GB1134389A (en) |
| NL (1) | NL6715657A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2711130C2 (en) * | 1977-03-15 | 1983-08-25 | Bayer Ag, 5090 Leverkusen | Azo dyes |
-
1966
- 1966-11-22 DE DE19661644181 patent/DE1644181C3/en not_active Expired
-
1967
- 1967-10-23 CH CH1778867D patent/CH1778867A4/xx unknown
- 1967-10-23 CH CH1478867A patent/CH511324A/en not_active IP Right Cessation
- 1967-10-23 CH CH1478867D patent/CH1478867A4/xx unknown
- 1967-10-31 GB GB4942167A patent/GB1134389A/en not_active Expired
- 1967-11-17 NL NL6715657A patent/NL6715657A/xx unknown
- 1967-11-22 BE BE706921D patent/BE706921A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1644181B2 (en) | 1974-06-27 |
| NL6715657A (en) | 1968-05-24 |
| CH1778867A4 (en) | 1971-04-30 |
| CH1478867A4 (en) | 1971-04-30 |
| GB1134389A (en) | 1968-11-20 |
| BE706921A (en) | 1968-04-01 |
| CH511324A (en) | 1971-04-30 |
| DE1644181A1 (en) | 1971-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |