GB2031926A - Dyestuffs - Google Patents
Dyestuffs Download PDFInfo
- Publication number
- GB2031926A GB2031926A GB7927356A GB7927356A GB2031926A GB 2031926 A GB2031926 A GB 2031926A GB 7927356 A GB7927356 A GB 7927356A GB 7927356 A GB7927356 A GB 7927356A GB 2031926 A GB2031926 A GB 2031926A
- Authority
- GB
- United Kingdom
- Prior art keywords
- textile materials
- monoazo dyestuff
- disperse monoazo
- synthetic textile
- halogen atom
- 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.)
- Withdrawn
Links
- 239000000463 material Substances 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 229920002994 synthetic fiber Polymers 0.000 claims abstract description 11
- 239000004758 synthetic textile Substances 0.000 claims abstract description 11
- 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 claims abstract description 10
- 239000000975 dye Substances 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 229920000728 polyester Polymers 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 239000004753 textile Substances 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 13
- 238000005859 coupling reaction Methods 0.000 claims description 11
- 230000008878 coupling Effects 0.000 claims description 10
- 238000010168 coupling process Methods 0.000 claims description 10
- 150000004982 aromatic amines Chemical class 0.000 claims description 5
- 150000001989 diazonium salts Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 abstract description 2
- 229920002647 polyamide Polymers 0.000 abstract description 2
- 229920002678 cellulose Polymers 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- -1 methoxy, ethoxy, butoxy Chemical group 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- LXQOQPGNCGEELI-UHFFFAOYSA-N 2,4-dinitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O LXQOQPGNCGEELI-UHFFFAOYSA-N 0.000 description 2
- MGCGMYPNXAFGFA-UHFFFAOYSA-N 2-amino-5-nitrobenzonitrile Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C#N MGCGMYPNXAFGFA-UHFFFAOYSA-N 0.000 description 2
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000012505 colouration Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000010023 transfer printing Methods 0.000 description 2
- IAHOUQOWMXVMEH-UHFFFAOYSA-N 2,4,6-trinitroaniline Chemical compound NC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O IAHOUQOWMXVMEH-UHFFFAOYSA-N 0.000 description 1
- RIYSFSQPHCAGLS-UHFFFAOYSA-N 2-amino-3,5-dinitrobenzonitrile Chemical compound NC1=C(C#N)C=C([N+]([O-])=O)C=C1[N+]([O-])=O RIYSFSQPHCAGLS-UHFFFAOYSA-N 0.000 description 1
- CGPPWNTVTNCHDO-UHFFFAOYSA-N 2-bromo-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Br CGPPWNTVTNCHDO-UHFFFAOYSA-N 0.000 description 1
- GLUCALKKMFBJEB-UHFFFAOYSA-N 2-bromo-6-chloro-4-nitroaniline Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Br GLUCALKKMFBJEB-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YBNCIUJKMVRSGZ-UHFFFAOYSA-N N-(3-aminophenyl)-N-cyclohexylacetamide Chemical compound C1(CCCCC1)N(C1=CC(=CC=C1)N)C(C)=O YBNCIUJKMVRSGZ-UHFFFAOYSA-N 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 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
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- BIXZHMJUSMUDOQ-UHFFFAOYSA-N dichloran Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl BIXZHMJUSMUDOQ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- ZIDDNNKRDWQBAH-UHFFFAOYSA-N hexyl N-[3-(cyclohexylamino)phenyl]carbamate Chemical compound C1(CCCCC1)NC1=CC(=CC=C1)NC(=O)OCCCCCC ZIDDNNKRDWQBAH-UHFFFAOYSA-N 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- YZJIIHXHXHSQPU-UHFFFAOYSA-N n-[3-(cyclohexylamino)phenyl]propanamide Chemical compound CCC(=O)NC1=CC=CC(NC2CCCCC2)=C1 YZJIIHXHXHSQPU-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 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 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 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
- 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
- C09B29/081—Amino benzenes free of acid groups characterised by the amino group substituted amino group unsubstituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino, aralkylamino or arylamino
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Disperse monoazo dyestuffs having the general formula: <IMAGE> wherein R represents hydrogen or an alkyl or alkoxy group which may be further substituted, Y represents a hydrogen atom, a halogen atom or a nitro group, and Z represents a halogen atom, a cyano group or a nitro group. The dyes are applicable to synthetic textile materials e.g. cellulose esters, polyamides and especially aromatic polyester textile materials.
Description
SPECIFICATION
Dyestuffs
This invention relates to dyestuffs and more particularly to disperse monoazo dyestuffs based on secondary amine coupling components.
According to the present invention there are provided disperse monoazo dyestuffs having the general formula:
wherein R represents hydrogen, or an alkyl or alkoxy group which may be further substituted,
Y represents a hydrogen atom, or halogen atom or a nitro group, and
Z represents a halogen atom, a cyano group or a nitro group.
Examples of the alkyl groups represented by Rare methyl, ethyl, n-propyl, isopropyl, n-butyl, pentyl and octyl.
Examples of the alkoxy groups represented by Rare methoxy, ethoxy, butoxy and hexyloxy, and examples of substituted alkoxy groups are alkoxyalkoxy groups, especially lower alkoxy lower alkoxy groups, for example, ss-methoxyethoxy and p-ethoxyethoxy.
Further substituents which may be present on the alkyl and alkoxy groups include halogen atoms and alkoxy groups.
It is preferred that the alkoxy groups represented by R are lower alkoxy groups.
Examples of halogen atoms represented by Y and Z are chlorine and bromine atoms.
In this specification the term "lower alkoxy" means an alkoxy group which contains from 1 to 4 carbon atoms.
According to a further feature of the invention there is provided a process for the manufacture of disperse monoazo dyestuffs having the above-defined formula (I) which comprises diazotising an arylamine having the formula:
and coupling the diazonium compound so obtained on to a coupling component having the formula:
wherein R, Y and Z have the meanings stated above.
Examples of the arylamines of formula (II) which may be used in the process are 2-chloro-4-nitroaniline, 2-cyano-4-nitroaniline, 2-bromo-4-nitroaniline, 2,4-dinitroaniline, 2,6-dibromo-4-nitroanailine, 2,6-dichloro4-nitroaniline, 2-bromo-6-chloro-4-nitroaniline, 2,4,6-trinitroaniline, 2-cyano-4, 6-dinitroaniline, 2-chloro-(or bromo-) 6-cyano-4-nitroaniline and 2-chloro-(or bromo-) 4,6-dinitroaniline.
Examples of the coupling components of formula (III) which may be used are N-cyclohexyl-maminoacetanilide, N-cyclohexyl-m-propionylaminoaniline, N-cyclohexyl-m.butyrylaminoaniline, Ncyclohexyl-m-hexanoylaminoaniline, N-cyclohexyl-m-nonanoylaminoaniline, N-cyclohexyl-mformylaminoaniline, N.cyclohexyl-m-methoxycarbonylaminoaniline, N-cyclohexyl-methoxycarbonylaminoaniline, N-cyclohexyl-m-butoxycarbonylaminoaniline, N-cyclohexyl-m-(p- methoxyethoxycarbonylami no)aniline, N-cyclohexyl-m-hexyloxycarbonylaminoaniline and N-cyclohexyl m-(-ethoxyethoxycarbonylamino)aniline.
The diazotisation and coupling may be carried out by known methods for these reactions. For example, the process may be carried out by adding sodium nitrite to a solution or dispersion of the arylamine in hydrochloric acid, sulphuric acid, an aqueous solution of sulphuric acid or a mixture of hydrochloric acid or sulphuric acid with an organic acid such as acetic and/or propionic acid, or by stirring the arylamine with nitrosylsulphuric acid, followed by addition of the resulting solution or dispersion of the diazonium compound thus obtained to a solution of the coupling component in water or in a mixture of water and a water-miscible organic liquid, if necessary adjusting the pH of the mixture to facilitate the coupling reaction, and finally isolating the resulting dyestuff by conventional methods.
According to a yet further feature of the invention there is provided a method for the colouration of synthetic textile materials which comprises applying to the said synthetic textile materials from an aqueous medium a monoazo dyestuff as hereinbefore defined.
The dyestuffs of the present invention may be applied to synthetic textile materials by dyeing, padding or printing methods in the form of aqueous dispersions which are prepared by conventional methods for example, by milling the dyestuffs with water and a suitable dispersing agent such as the sodium salt of a naphthalene-2-sulphonic acid/formaldehyde condensate.
Examples of synthetic textile materials to which the dyestuffs may be applied are textile materials fabricated from secondary cellulose acetate, cellulose triacetate, polyamides such as poly(hexamethylene adipamide) and above all aromatic polyesters such as polyethylene terephthalate.
The dyestuffs may also be applied to synthetic textile materials by known methods of transfer colour printing such as sublimation transfer printing, optionally under reduced pressure, and wet transfer printing.
The dyestuffs also find application for the melt colouration of polymers such as aromatic polyesters.
When applied to synthetic textile materials as indicated above, the dyestuffs of the present invention provide bright bluish-red to violet shades having good fastness to the tests conventionally applied to coloured synthetic textile materials and in particular good dyeing properties and tinctorial strength.
The invention is illustrated but not limited by the following Examples in which parts and percentages are by weight.
Example 7 2-Chloro-4-nitroaniline (3.45 parts) is dissolved in a mixture of glacial acetic acid (40 parts) and concentrated hydrochloric acid (6 parts) and diazotised at 0-1 0tC by addition of 2N-aqueous sodium nitrite solution (10 parts). The solution of the diazonium compound so obtained is added to a mixture of
N-cyclohexyl-m-aminoacetanilide (4.64 parts) in acetic acid (50 parts) and ice water (200 parts). The mixture is stirred for 1 hour, after which time the dyestuff is collected, washed well with water and recrystallized from aqueous acetone.
When applied in the form of an aqueous dispersion to aromatic polyester textile material a bright bluish-red shade is obtained.
The following table gives further Examples of dyestuffs of the invention which may be obtained by diazotising the amines listed in the second column and coupling with the secondary amines listed in the third column. The fourth column gives the shades obtained on aromatic polyester textile materials.
I ros-,le Diro Courwonent ! CouplS6 Coelponent | Sbzde 2 ow\ I Q -W ';"; 3 2 < 2 Rubine s 2 a' CL 5 od 2 S çi CL 6 Ze 2 e NH2 B, 7 NO- Ra \=a < CI wtolet
Z"pI. o Cn!tpenent | Coupling CoS nt | d B, NHCH IS ss > 9 Nli NH Viol-t 9 Ozh o2 NH t(:3 NhODC2h5 0 N NhCOC6hl3 11 2 2 t} 3 Bed --J NHcH2(C232 12 cuHy uHCOC H Cl 13 As Bubin, CN NdOOOCh3 14 021 2 '(H Red ri.lt 5 n h Ch3 15 \NH
Claims (8)
1. A disperse monoazo dyestuff having the general formula:
wherein R represents hydrogen or an alkyl or alkoxy group which may be further substituted,
Y represents a hydrogen atom, a halogen atom or a nitro group, and
Z represents a halogen atom, a cyano group or a nitro group.
2. A disperse monoazo dyestuff as claimed in claim 1 and specially identified herein.
3. A process for the manufacture of a disperse monoazo dyestuff as defined in claim 1 which comprises diazotising an arylamine having the formula:
and coupling the diazonium compound so obtained with a coupling component having the formula:
wherein R, Y and Z have the meanings stated in claim 1.
4. A process as claimed in claim 3 conducted substantially as hereinbefore described with reference to any one of the foregoing Examples.
5. A disperse monoazo dyestuff whenever manufactured by a method claimed in claim 3 or claim 4.
6. A process for the coloration of synthetic textile materials which comprises applying thereto a disperse monoazo dyestuff as claimed in any one of claims 1, 2 and 5.
7. A process as claimed in claim 6 wherein the synthetic textile material is an aromatic polyester textile material.
8. Synthetic textile materials whenever coloured by the process claimed in claim 6 or claim 7.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7836176 | 1978-09-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2031926A true GB2031926A (en) | 1980-04-30 |
Family
ID=10499551
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7927356A Withdrawn GB2031926A (en) | 1978-09-08 | 1979-08-06 | Dyestuffs |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5538879A (en) |
| DE (1) | DE2935012A1 (en) |
| FR (1) | FR2435503A1 (en) |
| GB (1) | GB2031926A (en) |
| IT (1) | IT1122518B (en) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1794159A1 (en) * | 1968-09-17 | 1971-11-18 | Basf Ag | New, water-insoluble azo dyes |
| DE2028395A1 (en) * | 1969-06-16 | 1970-12-23 | ||
| BE759527A (en) * | 1969-11-28 | 1971-04-30 | Bayer Ag | CONTINUOUS DYEING PROCESS OF SYNTHETIC FIBROUS MATERIALS |
-
1979
- 1979-08-06 GB GB7927356A patent/GB2031926A/en not_active Withdrawn
- 1979-08-28 IT IT25317/79A patent/IT1122518B/en active
- 1979-08-30 DE DE19792935012 patent/DE2935012A1/en not_active Withdrawn
- 1979-09-05 JP JP11301479A patent/JPS5538879A/en active Pending
- 1979-09-07 FR FR7922425A patent/FR2435503A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5538879A (en) | 1980-03-18 |
| FR2435503A1 (en) | 1980-04-04 |
| IT7925317A0 (en) | 1979-08-28 |
| DE2935012A1 (en) | 1980-03-20 |
| IT1122518B (en) | 1986-04-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |