CA1091655A - Dicyano azo dyes having ether substituted aniline couplers - Google Patents
Dicyano azo dyes having ether substituted aniline couplersInfo
- Publication number
- CA1091655A CA1091655A CA313,170A CA313170A CA1091655A CA 1091655 A CA1091655 A CA 1091655A CA 313170 A CA313170 A CA 313170A CA 1091655 A CA1091655 A CA 1091655A
- Authority
- CA
- Canada
- Prior art keywords
- dicyano
- dyes
- azo dyes
- substituted aniline
- ether substituted
- 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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title abstract description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title abstract 3
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 title 1
- 239000000987 azo dye Substances 0.000 title 1
- 125000001033 ether group Chemical group 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 3
- 239000000975 dye Substances 0.000 abstract description 13
- -1 2,6-dicyano-4-nitrophenylazo moiety Chemical group 0.000 abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 3
- 229920000728 polyester Polymers 0.000 abstract description 3
- 239000004721 Polyphenylene oxide Substances 0.000 abstract description 2
- 239000001045 blue dye Substances 0.000 abstract description 2
- 239000000835 fiber Substances 0.000 abstract description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 2
- 229920000570 polyether Polymers 0.000 abstract description 2
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- YMZIFDLWYUSZCC-UHFFFAOYSA-N 2,6-dibromo-4-nitroaniline Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1Br YMZIFDLWYUSZCC-UHFFFAOYSA-N 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 229920006221 acetate fiber Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- FZERHIULMFGESH-UHFFFAOYSA-N methylenecarboxanilide Natural products CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000005406 washing 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/40—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms
- C09B43/42—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms by substituting radicals containing hetero atoms for —CN radicals
-
- 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0813—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by OH, O-C(=X)-R, O-C(=X)-X-R, O-R (X being O,S,NR; R being hydrocarbonyl)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
TITLE
DICYANO AZO DYES HAVING ETHER SUBSTITUTED ANILINE COUPLERS
Abstract of the Disclosure This invention relates to blue dyes containing a 2,6-dicyano-4-nitrophenylazo moiety in combination with an aniline coupler containing m-acylamido groups and polyether groups on the coupler nitrogen atom. The dyes have excellent fastness properties and very desirable blue shades when dyed on polyester and cellulose acetate fibers.
DICYANO AZO DYES HAVING ETHER SUBSTITUTED ANILINE COUPLERS
Abstract of the Disclosure This invention relates to blue dyes containing a 2,6-dicyano-4-nitrophenylazo moiety in combination with an aniline coupler containing m-acylamido groups and polyether groups on the coupler nitrogen atom. The dyes have excellent fastness properties and very desirable blue shades when dyed on polyester and cellulose acetate fibers.
Description
~g~655 This invention relates to blue dyes containing a 2,6-dicyano-4-nitrophenylazo moiety in combination with an aniline coupler containing m-acylamido group and polyether group on the coupler nitrogen atom. The dyes have excellent properties includ-ing fastness and very desirable blue shades on polyester andcellulose acetate fibers.
The dyes of this invention have the following general formula:
ÇN
OzN~ -N=N
=~ t=- zH40C2H40Rz CN NHCOR
wherein R is selected from alkoxy of 1-4 carbons, phenyl, and straight or branched chain alkyl of 1-4 ca}bons which may be sub-stituted with phenoxy and phenyl.
Rl is straight chain or branched chain alkyl of 1-6 carbons- and R2 is straight chain or branched chain alkyl of 1-4 carbons.
The present dyes exhibit improved properties such as dyeability by a variety of methods, build, exhaustion, leveling, pH stability, fas~ness to light, wash and sublimation, depth of shade and color uniformity under various wavelength light, essen-tially no blooming, and uniformity of dyeing under a variety of temperature and pressure conditions.
Various exemplary dyes of the present invention are shown in Table 1 herein. A particularly good dye is that of the formula ~09~655 ~N
02N~ N=N-~ /a-~-CzH40C2H40C2H5 This invention will be further illustrated by the follow-ing examples although it will be understood that these examples are included merely for purposes of illustration and are not intended to limit the scope of the invention.
Preparation of the Couplers 1. Preparation of 3~-{[2-(2-ethoxyethyoxy)ethyl]ethyl amino}
acetanilide To m-acetamidoaniline (30.0 g.) is added 2-(2-ethoxyethoxy)-- ethanol (250 ml.) and Raney nickel (25.0 g). The mixture is heated for 12 hr. at 175~C. and 200 psi. nitrogen in an autoclave. The Raney nickel is removed by filtration. To this product is added potassium carbonate (27.6 g.) and iodoethane (46.8 g.) and the reaction mixture is heated at 120C. for 3 hr. The reaction mixture is drowned into water (800 ml.) and extracted with chloroform. The excess solvent is removed by distillation. The product is a brown viscous oil.
The following specific couplers were prepared as in Example 1:
3'-1Ethyl[2-(2-isobutoxyethoxy)ethyl]amino}benzanilide.
3'-{[2-(2-Ethoxyethoxy)ethyl]ethylamino}benzanilide.
EXAMPLE`4 3'-{Ethyl[2-(2-isopropoxyethoxy)ethyl]amino}acetanilide.
3'-{[2-(2-methoxyethoxy)ethyl]ethylamino}benza~ilide.
3'-{[2-(2-butoxyethoxy)ethyl]ethylamino}acetanilide.
~916S5 Preparation of Dyes Sodium nitrite (7.2 g.) is added gradually to 50 ml. of conc.
H2S04. The solution is cooled and 100 ml. of 1:5 acid (1 part propionic and 5 parts acetic) is added below 15C. To this mixture is added 2,6-dibromo-4-nitroaniline (29.6 g.
0.1 m.) followed by 100 ml. of 1:5 acid, all below 5C. The reaction mixture is stirred at 0-5C. for 2 hr. The couplers of Examples 1-6 above (0.01 moles) are dissolved in 40 ml.
of 1:5 acid, chilled to below 5C., and to each is added a 0.01 mole aliquot of the above diazonium salt solution. The coupling mixtures are allowed to stand for 1 hr. The dyes are precipitated by the addition of water, collected by filtration, washed with water and dried in air. If needed, the dyes are purified by slurrying in hot methanol, cooling, filtering and washing with methanol.
EXAMPLES 7-12 - Replacement of Bromine Atoms With Cyano Groups A mixture of (0.002 m) of each bromo dye corresponding to Examples 1-6, 0.4 g. cuprous cganide, and 30 ml. of N,N-dimethylformamide is heated at 95-100C. for 30 min. The reaction mixture is drowned in water. The resulting dicyano dyes are collected by filtration, washed with water and dried in air.
These cyano dyes are shown in Table 1 and produce bright blue shades on polyester fibers. Similar preparations are employed for the other dyes 13-21 of Table 1.
~as~6ss Table 1 ÇN
02N~ o-N=N-~ -N
=~ \CzH40C2HoOR~
CN NHCOR
EY~ample No. R Rl R2 6 5 C2H5 CH2CH(CH3)2 CH3 C2H5 CH(CH3)2 12 CH3 C2H5 C4Hg-n 13 CH2CH(CH3)2 CH2CH2C 3 C2H5 14 C2H5 CH2CH(CH3)2 C2H5 16 CH3 C~l(CH3)C2H5 C2H5 17 CH3 CH(CH3)C4Hg-n C2H5 The invention has been described in detail with particular reference to preferred embodiments thereof, but it will be understood that variations and modifications can be effected within the spirit and scope of the invention.
The dyes of this invention have the following general formula:
ÇN
OzN~ -N=N
=~ t=- zH40C2H40Rz CN NHCOR
wherein R is selected from alkoxy of 1-4 carbons, phenyl, and straight or branched chain alkyl of 1-4 ca}bons which may be sub-stituted with phenoxy and phenyl.
Rl is straight chain or branched chain alkyl of 1-6 carbons- and R2 is straight chain or branched chain alkyl of 1-4 carbons.
The present dyes exhibit improved properties such as dyeability by a variety of methods, build, exhaustion, leveling, pH stability, fas~ness to light, wash and sublimation, depth of shade and color uniformity under various wavelength light, essen-tially no blooming, and uniformity of dyeing under a variety of temperature and pressure conditions.
Various exemplary dyes of the present invention are shown in Table 1 herein. A particularly good dye is that of the formula ~09~655 ~N
02N~ N=N-~ /a-~-CzH40C2H40C2H5 This invention will be further illustrated by the follow-ing examples although it will be understood that these examples are included merely for purposes of illustration and are not intended to limit the scope of the invention.
Preparation of the Couplers 1. Preparation of 3~-{[2-(2-ethoxyethyoxy)ethyl]ethyl amino}
acetanilide To m-acetamidoaniline (30.0 g.) is added 2-(2-ethoxyethoxy)-- ethanol (250 ml.) and Raney nickel (25.0 g). The mixture is heated for 12 hr. at 175~C. and 200 psi. nitrogen in an autoclave. The Raney nickel is removed by filtration. To this product is added potassium carbonate (27.6 g.) and iodoethane (46.8 g.) and the reaction mixture is heated at 120C. for 3 hr. The reaction mixture is drowned into water (800 ml.) and extracted with chloroform. The excess solvent is removed by distillation. The product is a brown viscous oil.
The following specific couplers were prepared as in Example 1:
3'-1Ethyl[2-(2-isobutoxyethoxy)ethyl]amino}benzanilide.
3'-{[2-(2-Ethoxyethoxy)ethyl]ethylamino}benzanilide.
EXAMPLE`4 3'-{Ethyl[2-(2-isopropoxyethoxy)ethyl]amino}acetanilide.
3'-{[2-(2-methoxyethoxy)ethyl]ethylamino}benza~ilide.
3'-{[2-(2-butoxyethoxy)ethyl]ethylamino}acetanilide.
~916S5 Preparation of Dyes Sodium nitrite (7.2 g.) is added gradually to 50 ml. of conc.
H2S04. The solution is cooled and 100 ml. of 1:5 acid (1 part propionic and 5 parts acetic) is added below 15C. To this mixture is added 2,6-dibromo-4-nitroaniline (29.6 g.
0.1 m.) followed by 100 ml. of 1:5 acid, all below 5C. The reaction mixture is stirred at 0-5C. for 2 hr. The couplers of Examples 1-6 above (0.01 moles) are dissolved in 40 ml.
of 1:5 acid, chilled to below 5C., and to each is added a 0.01 mole aliquot of the above diazonium salt solution. The coupling mixtures are allowed to stand for 1 hr. The dyes are precipitated by the addition of water, collected by filtration, washed with water and dried in air. If needed, the dyes are purified by slurrying in hot methanol, cooling, filtering and washing with methanol.
EXAMPLES 7-12 - Replacement of Bromine Atoms With Cyano Groups A mixture of (0.002 m) of each bromo dye corresponding to Examples 1-6, 0.4 g. cuprous cganide, and 30 ml. of N,N-dimethylformamide is heated at 95-100C. for 30 min. The reaction mixture is drowned in water. The resulting dicyano dyes are collected by filtration, washed with water and dried in air.
These cyano dyes are shown in Table 1 and produce bright blue shades on polyester fibers. Similar preparations are employed for the other dyes 13-21 of Table 1.
~as~6ss Table 1 ÇN
02N~ o-N=N-~ -N
=~ \CzH40C2HoOR~
CN NHCOR
EY~ample No. R Rl R2 6 5 C2H5 CH2CH(CH3)2 CH3 C2H5 CH(CH3)2 12 CH3 C2H5 C4Hg-n 13 CH2CH(CH3)2 CH2CH2C 3 C2H5 14 C2H5 CH2CH(CH3)2 C2H5 16 CH3 C~l(CH3)C2H5 C2H5 17 CH3 CH(CH3)C4Hg-n C2H5 The invention has been described in detail with particular reference to preferred embodiments thereof, but it will be understood that variations and modifications can be effected within the spirit and scope of the invention.
Claims (3)
1. A compound having the formula:
wherein R is selected from alkoxy of 1-4 carbons, phenyl, and straight or branched chain alkyl of 1-4 carbons which may be substituted with phenoxy and phenyl;
R1 is straight chain or branched chain alkyl of 1-6 carbons; and R2 is straight chain or branched chain alkyl of 1-4 carbons.
wherein R is selected from alkoxy of 1-4 carbons, phenyl, and straight or branched chain alkyl of 1-4 carbons which may be substituted with phenoxy and phenyl;
R1 is straight chain or branched chain alkyl of 1-6 carbons; and R2 is straight chain or branched chain alkyl of 1-4 carbons.
2. A compound of Claim 1 having the formula wherein R is straight chain or branched chain alkyl of 1-4 carbons.
3. A compound of Claim 1 having the formula
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88971678A | 1978-03-24 | 1978-03-24 | |
| US889,716 | 1978-03-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1091655A true CA1091655A (en) | 1980-12-16 |
Family
ID=25395659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA313,170A Expired CA1091655A (en) | 1978-03-24 | 1978-10-12 | Dicyano azo dyes having ether substituted aniline couplers |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS54131628A (en) |
| BE (1) | BE875084A (en) |
| CA (1) | CA1091655A (en) |
| DE (1) | DE2911311A1 (en) |
| FR (1) | FR2420555A1 (en) |
| GB (1) | GB2017137B (en) |
| HK (1) | HK4483A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59168069A (en) * | 1983-03-15 | 1984-09-21 | Gosei Senriyou Gijutsu Kenkyu Kumiai | Dye blend for polyester fiber |
| CN108410211B (en) * | 2018-03-22 | 2020-05-05 | 浙江万丰化工股份有限公司 | Blue azo dye composition and application thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1290915B (en) * | 1966-02-17 | 1969-03-20 | Bayer Ag | Process for dyeing and printing fiber materials made from aromatic polyesters and cellulose acetates |
| CA994333A (en) * | 1972-04-07 | 1976-08-03 | Kunihiko Imada | Azo disperse dye mixtures |
| JPS5845469B2 (en) * | 1975-07-10 | 1983-10-11 | 住友化学工業株式会社 | Mizufuyoseimono Azosenriyounoseihou |
-
1978
- 1978-10-12 CA CA313,170A patent/CA1091655A/en not_active Expired
-
1979
- 1979-03-22 DE DE19792911311 patent/DE2911311A1/en not_active Withdrawn
- 1979-03-22 FR FR7907249A patent/FR2420555A1/en not_active Withdrawn
- 1979-03-23 GB GB7910213A patent/GB2017137B/en not_active Expired
- 1979-03-23 BE BE0/194211A patent/BE875084A/en unknown
- 1979-03-24 JP JP3498979A patent/JPS54131628A/en active Granted
-
1983
- 1983-01-27 HK HK4483A patent/HK4483A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2420555A1 (en) | 1979-10-19 |
| JPS54131628A (en) | 1979-10-12 |
| HK4483A (en) | 1983-01-27 |
| DE2911311A1 (en) | 1979-10-04 |
| GB2017137A (en) | 1979-10-03 |
| JPS6244584B2 (en) | 1987-09-21 |
| GB2017137B (en) | 1982-08-18 |
| BE875084A (en) | 1979-09-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |