GB1569062A - Disazo dyestuffs - Google Patents
Disazo dyestuffs Download PDFInfo
- Publication number
- GB1569062A GB1569062A GB7698/78A GB769878A GB1569062A GB 1569062 A GB1569062 A GB 1569062A GB 7698/78 A GB7698/78 A GB 7698/78A GB 769878 A GB769878 A GB 769878A GB 1569062 A GB1569062 A GB 1569062A
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- Prior art keywords
- optionally substituted
- methyl
- denotes
- chlorine
- alkyl
- Prior art date
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- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 149
- 229910052739 hydrogen Inorganic materials 0.000 claims description 115
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 56
- -1 methoxy, ethoxy Chemical group 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 36
- 239000000975 dye Substances 0.000 claims description 33
- 239000000460 chlorine Substances 0.000 claims description 29
- 229910052801 chlorine Inorganic materials 0.000 claims description 29
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- 229910006069 SO3H Inorganic materials 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- 229910052702 rhenium Inorganic materials 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 7
- 238000004043 dyeing Methods 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 229910004727 OSO3H Inorganic materials 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 229920002994 synthetic fiber Polymers 0.000 claims description 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- RJSYPKWVIJGNLO-UHFFFAOYSA-N CCOClOC Chemical group CCOClOC RJSYPKWVIJGNLO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 14
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 229910019567 Re Re Inorganic materials 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 19
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000012362 glacial acetic acid Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000004952 Polyamide Substances 0.000 description 7
- 229920002647 polyamide Polymers 0.000 description 7
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- 235000010288 sodium nitrite Nutrition 0.000 description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 5
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-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
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- AZLXCBPKSXFMET-UHFFFAOYSA-M sodium 4-[(4-sulfophenyl)diazenyl]naphthalen-1-olate Chemical compound [Na+].C12=CC=CC=C2C(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 AZLXCBPKSXFMET-UHFFFAOYSA-M 0.000 description 2
- 125000005975 2-phenylethyloxy group Chemical group 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- RPJXLEZOFUNGNZ-UHFFFAOYSA-N 5-methoxy-2-methylaniline Chemical compound COC1=CC=C(C)C(N)=C1 RPJXLEZOFUNGNZ-UHFFFAOYSA-N 0.000 description 1
- MPVDXIMFBOLMNW-ISLYRVAYSA-N 7-hydroxy-8-[(E)-phenyldiazenyl]naphthalene-1,3-disulfonic acid Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1\N=N\C1=CC=CC=C1 MPVDXIMFBOLMNW-ISLYRVAYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 101100496104 Mus musculus Clec2d gene Proteins 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 101100274534 Rattus norvegicus Clec2d11 gene Proteins 0.000 description 1
- 101100274532 Rattus norvegicus Ocil gene Proteins 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- NJDNXYGOVLYJHP-UHFFFAOYSA-L disodium;2-(3-oxido-6-oxoxanthen-9-yl)benzoate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=CC(=O)C=C2OC2=CC([O-])=CC=C21 NJDNXYGOVLYJHP-UHFFFAOYSA-L 0.000 description 1
- LCZPIYCNOWJWPQ-UHFFFAOYSA-I disodium;chromium(3+);1-[(2-oxidonaphthalen-1-yl)diazenyl]-4-sulfonaphthalen-2-olate;3-oxido-4-[(2-oxidonaphthalen-1-yl)diazenyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].[Cr+3].C12=CC=CC=C2C(S(=O)(=O)O)=CC([O-])=C1N=NC1=C([O-])C=CC2=CC=CC=C12.C1=CC=C2C(N=NC3=C4C=CC=CC4=CC=C3[O-])=C([O-])C=C(S([O-])(=O)=O)C2=C1 LCZPIYCNOWJWPQ-UHFFFAOYSA-I 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- MLVYOYVMOZFHIU-UHFFFAOYSA-M sodium;4-[(4-anilinophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(S(=O)(=O)[O-])=CC=C1N=NC(C=C1)=CC=C1NC1=CC=CC=C1 MLVYOYVMOZFHIU-UHFFFAOYSA-M 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/04—Disazo dyes from a coupling component "C" containing a directive amino group
- C09B31/043—Amino-benzenes
- C09B31/047—Amino-benzenes containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof
-
- 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
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
(54) DISAZO DYESTUFFS
(71) We, BAYER AKTIENGESELLSCHAFT, a body corporate organised under the laws of Federal Republic of Germany of Leverkusen,
Germany, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement::- The invention provides disazo dyestuffs which contain only one acid group and which, in the form of the free acids, correspond to the formula
wherein
p is 0 or 1,
X denotes OH, NH-SO2-R8, N(Rg)-alkylene-OSO3H, N(R9)-alkylene-SO3H, N(R9)-arylene-SO3H, N(R9Yarylene-CH2-SO3H or N(R9)-arylene-SO2-NH-SO2-R8, Z denotes acyl,
R1 and R2 denote hydrogen or non-ionic substituents, R3, R4 and R5 denote hydrogen, optionally substituted alkyl, optionally substituted
aralkyl, optionally substituted aryl, halogen, optionally substituted alkoxy,
optionally substituted aryloxy, optionally substituted aralkoxy or
optionally substituted acylamino; or
R4 and R3 together denote the remaining members of a fused benzene
ring, Re and R9 denote hydrogen or optionally substituted alkyl, R, denotes hydrogen, optionally substituted alkyl, optionally substituted
aryl or optionally substituted aralkyl and R9 denotes optionally substituted alkyl, optionally substituted aralkyl,
optionally substituted aryl or dialkylamino.
As used herein the term "non-ionic substituents" means a substituent
which does not dissociate under the condition of production or use of the
dyestuff.
Preferred non-ionic substituents R, and R2 are halogen, cyano, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryl, trifluoromethyl, nitro, thiocyano, optionally substituted carbamoyl, optionally substituted sulphamoyl, optionally substituted alkylsulphonyl and optionally substituted arylsulphonyl. Preferred substituents of the carbamoyl and sulphamoyl groups are optionally substituted alkyl, optionally substituted aralkyl and optionally substituted aryl.
Preferred acyl radicals Z and in the acylamino groups R2, R4 and R5 are optionally substituted alkylcarbonyl, optionally substituted arylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted aryloxycarbonyl, optionally substituted alkylsulphonyl, optionally substituted aralkylsulphonyl and optionally substituted arylsulphonyl.
As used herein the term "acyl" means any organic "acid group", the hydrogen atom of which is easily replaced by for example a metal atom and includes, in addition to those acyl radicals mentioned above, an activated pyrimidinyl, an alkoxycarbonyl and a triazinyl radical.
Preferred alkyl radicals R1, R2, R3, R4, R5, R6 R7, R8 and R9, in the alkylsulphonyl groups and as substituted of the carbamoyl and sulphamoyl radicals are preferably those with I to 4 carbon atoms, which may be substituted by halogen, cyano, hydroxyl or C,-C4-alkoxy.
Preferred aryl radicals R1, R2, R3, R4, R5, R7 and R8, in the arylcarbonyl and arylsulphonyl groups and as substituents of the carbamoyl and sulphamoyl groups are phenyl and naphthyl radicals which are optionally substituted by phenyl, C1-C4 alkyl, halogen nitro or C1-C4 alkoxy.
Preferred aralkyl groups R3, R4, R5, R7 and R8 in the aralkylsulphonyl groups and as substituents of the carbamoyl and sulphamoyl radicals are benzyl and 2phenylethyl, which may be substituted in the phenyl radical by C1-C4-alkyl, C1-C4 alkoxy, halogen, nitro or cyano.
Preferred alkoxy groups R1, R2, R3, R4 and R5 and in the alkoxycarbonyl groups are C1-C4 alkoxy groups, which may be optionally substituted by hydroxyl, halogen or cyano.
Preferred aryloxy radicals R3, R4 and R5 and in the aryloxycarbonyl groups are phenyloxy or naphthyloxy radicals which are optionally substituted by phenyl, C1-C4 alkyl, halogen, nitro or C1-C4 alkoxy.
Preferred aralkyloxy groups R3, R4 and $5 and in the aralkyloxycarbonyl radicals are benzyloxy and 2-phenylethoxy groups, which may be substituted in the phenyl radical by C1-C4 alkyl, C1-C4 alkoxy, halogen, nitro or cyano.
The alkylenes as a constituent of the radicals X are preferred C2-C6 alkylene groups, which may be straight-chain or branched. The arylenes as a constituent of the substituents X are preferably phenylene radicals, which may be further substituted by C1-C4 alkyl, C1-C4 alkoxy, halogen, cyano or nitro.
The alkyl groups of the dialkylamino radicals Re preferably contain I to 4 carbon atoms. Preferred halogen atoms are fluorine, chlorine and bromine, especially chlorine and bromine.
Those dyestuffs which contain an acyl group Z which is not fibre-reactive are preferred.
Preferred dyestuffs within the formula I are those in which
p has the above mentioned meaning,
X denotes OH, NH-SO2-Re, N(R9)-(C2-C6) alkylene OSO3H,
N(R9)-(C2-C6) alkylene-SO3H, N(R9)-phenylene-SO3H, N(R9)-phenylene CH2-SO3H or N(R9)-phenylene-SO2NO-SO2-R8 wherein the phenylene
may be substituted by C1-C4 alkyl, C1-C4 alkoxy, halogen, cyano or nitro.
R, and R2 independently denote hydrogen, chlorine, bromine, methyl, ethyl,
methoxy, ethoxy, cyano, trifluoromethyl or phenoxy,
R3, R4, R5 and R6 independently denote hydrogen, C1-C4 alkyl, C1-Cd alkoxy, C1-C4 alkylcarbonylamino, benzoylamino, C1-C4 alkylsulphonyl
amino, phenylsulphonylamino c-c4 alkoxycarbonylamino or phenoxy
carbonylamino, wherein the phenyl nuclei may be substituted by methyl, ethyl,
methoxy, ethoxy, chlorine, bromine or cyano,
R, denotes hydrogen, C1-C4 alkyl which is optionally substituted by chlorine,
hydroxyl, cyano, benzyl or phenethyl,
R8 denotes C1-C4 alkyl or phenyl which is optionally substituted by methyl,
chlorine or bromine,
R9 denotes hydrogen, methyl or ethyl and
Z denotes C1-C4 alkylcarbonyl which is optionally substituted by cyano.
C1-C4 alkoxy, phenoxy or phenyl, benzoyl which is optionally substituted by
C1-C4 alkyl, chlorine, bromine, nitro, cyano or C1-C4 alkoxy, C1-C4 alkyl
sulphonyl, phenylsulphonyl, phenoxycarbonyl or C1-C4 alkoxycarbonyl,
wherein the phenyl and phenoxy groups may be substituted by chlorine, C1-C4 alkyl, C1-C4 alkoxy or cyano.
Particularly preferred dyestuffs are those which, in the form of the free
acid, correspond to the formula
wherein
Z' denotes C1-C4 alkylcarbonyl, benzoyl which is optionally substituted
by methyl, methoxy or chlorine, phenylacetyl which is optionally
substituted by methyl, methoxy or chlorine or phenoxyacetyl which is
optionally substituted by methyl, methoxy or chlorine, X' denotes CH,
NH-SO2-R8', N(R9')-(C2-C4)-alkylene-OSO3H, N(R9')-(C2-C4)
alkylene-SO3H or
R, and R2 independently denote hydrogen, methyl, ethyl, chlorine,
bromine or trifluoromethyl R' and R4 independently denote hydrogen, methyl, ethyl, methoxy,
ethoxy, acetylamino, methylsulphonylamino or phenylsulphonylamino,
R5' denotes hydrogen, methyl, ethyl, methoxy, ehtoxy or acetylamino,
R6' denotes hydrogen, or mehyl,
R7' denotes hydrogen, methyl, ethyl, 2-cyanoethyl, 2-chloroethyl, benzyl
or phenethyl, R8 denotes C1-C4 alkyl or phenyl which is optionally substituted by
methyl, chlorine or bromine and Rg denotes hydrogen, methyl or ethyl.
Especially preferred compounds are those which, in the form of the freee acid, correspond to the formula
wherein
X', R; and Ré have the abovementioned meaning,
R'2 denotes hydrogen or methyl, R'3 denotes hydrogen, methyl or methoxy, R'4 denotes hydrogen, methyl, methoxy, ethoxy or acetylamino, R5 denotes hydrogen, methyl or acetylamino and
Z" denotes acetyl, propionyl, benzoyl which is optionally substituted by
methyl, methoxy or chlorine, phenylacetyl which is optionally substituted
by methyl methoxy or chlorine, or phenoxyacetyl which is optionally
substituted by methyl, methoxy or chlorine.
The dyestuffs of the formula (I) are prepared by coupling diazotised aminoazo compounds of the formula
wherein
X, R1, R2, R3, R4 and p have the meaning already given, to amines of the formula
wherein RB, Re and R, have the meaning already given, and subsequently acylating the product, the radical Z wherein
Z has the meaning already given, being introduced.
The dyestuffs according to the invention are suitable for dyeing natural and synthetic fibre materials, in particular for dyeing polyamide fibres, in level yellow to orange shades of good colour yield and very good fastness to light and wet processing. The present invention accordingly further provides a process for dyeing a natural or synthetic fibre material comprising treating the material with a dyestuff of the present invention. The dyestuffs of the present invention are already absorbed well onto polyamide fibres in a neutral to weakly acid dyebath. Polyamides are understood here, in particluar, as those consisting of synthetic polyamides, such as E-polycaprolactam, or condensation products of adipic acid and hexamethylenediamine.The dyestuffs are used here either in the form of the free acid or in the form of their salts, in particular the alkali metal salts, preferably the sodium or potassium salts, as well as the ammonium salts.
Example 1.
13.65 g of p-sulphanilic acid are dissolved in 150 ml of water with 5 g of sodium hydroxide. Thereafter, 5 g of sodium nitrite are added. The resulting solution is added dropwise into a mixture of 500 g of ice and 50 ml of concentrated hydrochloric acid. The mixture is subsequently stirred at OOC for 2 hours, theexcess nitrite is destroyed with amidosulphonic acid, and a solution of 8.8 g of 2,5dimethylaniline in 100 ml of glacial acetic acid is added dropwise. The pH value is adjusted to about 4 with saturated sodium acetate solution. Thr dyestuff which has precipitated is filtered off and dried at about 40"C.
4.4 g of the dyestuff described above are stirred in 150 ml of 50 / by weight hydrochloric acid and diazotised at room temperature with 1 g of sodium nitrite, dissolved in 10 ml of water. 1.6 g of m-toluidine are dissolved in 50 ml of glacial acetic acid and the solution is added to the diazonium salt solution. The pH value is adjusted to about 4 with saturated sodium acetate solution. The dyestuff which has precipitated is filtered off and dried at about 40"C.
3 g of the disazo dyestuff described above are stirred in 60 ml of acetic anhydride and 20 ml of glacial acetic acid at 120"C for 2 hours. The mixture is allowed to cool to room temperature and the dyestuff which has precipitated of the formula
is filtered off, rinsed and dried at 400 C.
Dyeing Example.
0.1 g of the dyestuff prepared according to Example 1 is dissolved hot in 100 ml of water, 5 ml of ammonium acetate solution are added and the mixture is diluted with water to a volume of 500 ml. 10 g of a polyamide fabric are put into the dyebath, the dyebath is brought to the boil in the course of 20 minutes, 4 ml of I strength by weight acetic acid are added and the bath is kept at the boiling point for one hour. Thereafter, the fabric is rinsed and dried at 70 to 800 C.
A yellowish-tinged orange dyeing of very good fastness to light is obtained.
Further valuable dyestuffs with the indicated colour shades according to the following tables are prepared in a manner corresponding to that in Example 1.
No. R1 R2 R3 R4 R5 R7 Z 2 H H H H 5-CH3 H -CO-CH3 reddish-tinged yellow 3 H H CH3 H 5-CH3 H -CO-CH3 " 4 H H CH3 CH3 H H -CO-CH3 " 5 H H H CH3 H H -CO-CH3 " 6 H H H CH3 5-CH3 H -CO-CH3 " 7 H H H CH3 6-CH3 H -CO-CH3 " 8 H H -O-CH3 H 5-CH3 H -CO-CH3 yellowish-tinged orange 9 H H -O-CH3 CH3 5-CH3 H -CO-CH3 " 10 H H -CH3 -O-CH3 5-CH3 H -CO-CH3 " 11 H H H -O-CH3 5-CH3 H -CO-CH3 " 12 H H H -NH-CO-CH3 5-CH3 H -CO-CH3 " 13 H H -CH3 -NH-CO-CH3 5-CH3 H -CO-CH3 " 14 H H -O-CH3 -O-CH3 5-CH3 H -CO-CH3 orange 15 H H -O-CH3 -O-CH3 6-CH3 H -CO-CH3 " No. R1 R2 R3 R4 R5 R7 Z 16 H H -O-CH3 -O-CH3 H H -CO-CH3 orange 17 2-CH3 H H CH3 H H -CO-CH3 yellowish-tinged orange 18 2-H3 H -CH3 CH3 5-CH3 H -CO-CH3 " 19 2-CH3 H -CH3 H H H -CO-CH3 " 20 2-CH3 H -CH3 -CH3 H H -CO-CH3 " 21 2-CH3 H H -O-CH3 H H -CO-CH3 " 22 2-CH3 H CH3 O-CH3 H H -CO-CH3 " 23 2-CH3 H -OCH3 CH3 5-CH3 H " " 24 2-Cl H H H H H " " 25 2-Cl H H CH3 5-CH3 H " " 26 2-Cl H CH3 CH3 5-CH3 H " " 27 2-Cl H H O-CH3 6-CH3 H " orange 28 2-Cl H H NH-CO-CH3 H H " " 29 2-Cl H OCH3 NH-CO-CH3 5-CH2 H " reddish-tinged orange 30 2-O-CH3 H CH3 CH3 5-CH3 H " reddish-tinged yellow No.R1 R2 R3 R4 R5 R7 Z
a S-o o c o 0 9 oO M CD e c ' o r O M T a 1 Q orange n 2-CH3 t.
U UN Ú 33 2-CF3 H y. CH3 5C2He H 3 yellow 8 35 2-CF3 H CH3 CH3 5-NH-C0-CH3 H ,, orange 36 H H CH3 CH3 ,, H 37 H H OCH3 CH3 ,, H .,.
U 39 2-CH3 H H CH3 , d " u u m m ) = Vw z z I yellow 42 H H CH3 CH3 6-CH3 H -CO-C3H7 U U OUUUU U 3 U V V G U V C.) =- U V U V CJ V V r U U O : = = D V NC ~ U U V U U v U V U ~ > t m sD > 00 0E 0 H N n No.R1 R2 R3 R4 R5 R7 Z
3 -3 3 ^jb 9 c E: e, M T u ' Y 3 o~S 3 30 CD O C e, M 44 H 2" yellow 45 H H tf 1 2CH3 H Qd 8 2-CH3 H H CH3 6-O-CH3 H ,, yellowish-tinged U za QJ 49 2-Cl H 3: 3: CH3 H = C X U H II v Q = Cil3 m :m CL vss lo vl 51 H H Cil3 Cil3 5-CH3 H ,' reddish-tinged orange 52 H Il H CH3 5-CR3 C113 , m v m m m m m m m ~ 8 " ' m n 30 -m O u !;J O ~ v v rD v ;;;J v R i m m m = m ZJ ~ e e v x I I e n v x ~ = x ~ x x x ~ x ~ X x m m m ~ v v v D x : N N N N x x x ~ O1 t m 95 > 00 O ~ O1 t No. R1 R2 R3 R4 R5 R7 Z
a a 1 h b .f: 3 a a .O O a u I I k 56 2-Cl H H m . a u" e3: rr ,o V V E V 'V 58 m H qx m o "o ç V X V V i le | m V = ; 3 V 1 v X z to OVX V es c1 C X = m m m m m v7
No.R1 R2 R3 R4 R5 R7 Z 60 H H H H H H CO-CH3 reddish-tinged yellow 61 H H H CH3 3-CH3 H " " 62 H H CH3 H 3-CH3 H " " 63 H H CH3 CH3 H H " " 64 H H CH3 CH3 3-CH3 H " " 65 H H CH3 O-CH3 H H " " 66 H H CH3 O-CH3 3-CH3 H " yellowish-tinged orange 67 H H O-CH3 CH3 3-CH3 H " " 68 H H O-CH3 CH3 H H " " 69 H H O-CH3 O-CH3 H H " orange 70 H H O-CH3 O-CH3 3-CH3 H " " 71 4-CH3 6-CH3 O-CH3 O-CH3 3-CH3 C2H5 " reddish-tinged orange 72 4-O-CH3 H CH3 CH3 3-CH3 C2H5 " reddish-tinged yellow No.R1 R2 R3 R4 R5 R7 Z
o E o r o o ~ m w .~ 'Ct, ' Oc a =d Ct 73 H H CR3 2-CR3 C2He CO-CR3 reddish-tinged a íf) O Q Q 75 4-Cl It 8 76 6-Cl H H H 3-0-CR3 C2H3 77 6-Cl H CR3 CH3 H C3H3 ,, reddish-tinged V t Ú e" '3 cP 3 N N 6-Cl H N o" u u" 3: 3: I u 79 U U = H -s:" H Il 3-CR3 G UU O u uu~ u v c rn H OCR3 CR3 3-CR3 C2H4Cl n a rv m O m @ I m m m m v Z X v X v X ;;J e xa xa X xa ^ xa r CC X r X v r v X C X X X = : X = Q ~ D v v v t Ç c X X rn t V} xD > X : > > > F F > x x x No. R1 R2 R3 R4 R5 R7 Z
a 8 1 o E o 4 c: h 83 H H > > M o o W > E 84 H H CH3 H Q-s"s"l 85 H 8 8 8 8 U U V . u U . U e" ae" 3 '3 '3 = V V V V V V 86 H H OCR3 U 3-CR3 C2Re u" 87 H H CR3 OCR3 H QRe -co--o cH5 88 H H OCR3 OCR3 3-CR3 C2Rs ,' orange n 2-Cl 5-Cl H Im a U U U 3: 3: U O C U a a a a a rt = a X I V v !T: v Ú V O O V O = V V X X 5: = = X N e t m F oo ofi oo oo oo oo oo oo c o No. R1 R2 R3 R4 R5 R7 Z
-cl "M 71 -ri a E S S c E E r: vl 3 r: .5 h o 90 4Cl 6-Cl H OCR3 3-O-R3 C2RB | Z N - 3: I I N 4-CR3 6-CR3 H OJ 92 4-CR3 6-CR3 CR3 CR3 3-CR3 H 8 a I I 3s c" 93 6-Br H 3: e 3: U" vl 31 H vl CR3 a a H -CO-CR2-CN reddish-tinged I I I U c; cc, m I H: 96 H H H CR3 3-CR3 H ,, 97 4-CR3 6-CR3 H = 3-CR3 xa xa 3, yellowish-tinged O O v O v v v O rr V V V v X :C a a a v v v rv x x v c xo a a xu a V v V 1= vN v t ~ X t O ~ N eP m wo > No.R, R2 R3 R4 Rs R, Z
98 4-0-II 4-o < ) H H CH3 H H Oe reddish-tinged 99 4-Ot H CH3 CH3 3-CH, H Example 100.
18.1 g of 4-(N-methylsulphonyl-amidosulphonyl)-aniline are dissolved in 150 ml of water with 5 g of sodium hydroxide. Thereafter, 5 g of sodium nitrite are added. The resulting solution is added dropwise to a mixture of 500 g of ice and 50 ml of concentrated hydrochloric acid. The mixture is subsequently stirred at OOC for 2 hours, the excess nitrite is destroyed with amidosulphonic acid, and a solution of 10.3 g of 2-methyl-5-methoxyaniline in 100 ml of glacial acetic acid is added dropwise. The pH value is adjusted to about 4 with saturated sodium acetate solution. The dyestuff which has precipitated is filtered off and dried at about 40"C.
8.7 g of the dyestuff described above are stirred in 150 ml of half-concentrated hydrochloric acid and diazotised at room temperature with I g of sodium nitrite, dissolved in 10 ml of water. 1.6 g of m-toluidine are dissolved in 50 ml of glacial acetic acid and the solution is added to the diazonium salt solution. The pH is adjusted to about 4 with saturated sodium acetate solution. The dyestuff which has precipitated is filtered off and dried at 400 C.
3.6 g of the disazo dyestuff described above are stirred in 60 ml of acetic anhydride and 20 ml of glacial acetic acid at 1200C for 2 hours. The mixture is allowed to cool to room temperature and the dyestuff, which has precipitated, of the formula
is filtered off.
The dyestuff dyes polyamide fibres yellowish-tinged orange.
No.R8 R1 R2 R3 R4 R5 R7 R6 Z
-ct -cr -J s p, a -oM-oOOoo 3 , ~ 3 3 3 0 3 o ^ ^ < 3 ~ 5 vl "M LI - C L ti41 M e, b - * r c -ct E O O C) C a O u yellow o CR3 H H OCR, CR, 3-CR3 H H ,, yellowish-tinged 103 C,H3 2-CR3 H CR3 CR3 3-CR3 H 6-CR3 reddish-tinged orange = Ux H H CR3 v U U U U U 105 C3R7 2-OCR3 H CR3 H 3-CR3 H 5-CR3 ,, yellowish-tinged 0 106 C4Rq H H OC2He H 3-CR3 CR3 H u E c (4Ra 2-Cl 5-CR, x H H H H a m a a a a a a U CII, 2-Cl H H CR, 3-CR, H 6-qH, ,, reddish-tinged l yellow 3: 3: U U 5, U c.z H H CR, CR, 3-CR3 O 6-CR, v u a c a a a XN a a Xx u x v D v x x x v xa = x x x x x = m :s x a a OVI D U U = x > x > = cs u F b b os ob X X X X X X X w ~I o o o o o o o c ~ o No.R8 R1 R2 R3 R4 R5 R7 R6 Z
a a o o a bo a bo a ag s C I C P 9 6 ill CR, R H H CR, 3-CR, o W > yellow 112 | a Q U 113 CR, 2-CF, v OCR3 CR, 3-CR, I v '3m u X H : r CR, 3-CR, H X ,, reddish-tinged - Ir 115 ,, H H CR, CR, 3-CR3 H H z u 117 V I H CR, OCR, 3-CR, X H 31 31 ' e" I: 118 H v v E v v v m I n 3 3 'c^ 3n '30 v v v ,, v v CR, CR, 3-CR, c H d1d10Shtd a a a U xa = a = x O = v o kS o : ) v X n X :: X X X X X a v v C X X X = = a a v u u No R8 R1 R2 R3 R4 R5 R7 R6 Z
b X ea r e4 h e 3 r 9 120 > H CR, CR, 3-CR, R H 0 121 ,, 2-CR, 5-CR, H CR3 3C3Re C2H, H -COO%H5 122 H H CR3 CR, 3-CR, 3CRa H -CO-CR, 8 ,, H H H CR, 3-CR, 3-CR, H r X H H OCR, CR, H H H " yellowish-tinged - orange 125 2-CR, R H CR, H H H " reddish-tinged H3C yellow = a U va U OU U U 126 /\ 2-CR, H H NH-COCR, c 'r" e o) x x ::c orange a X a a a a U a 3 '3n 3 e" u e o u 128 ,, 2-Cl H CR, OCR, 3-CR3 3-CR, R -WCL a a = u x U x Ov x x x v a u v x m x x x x x m x V ' va V V Q V es rs x x x > n > > t 34 O c9 t m vD F 00 No.R8 R1 R2 R3 R4 R5 R7 R6 Z
a 3 g a ao E E s ea 3 en t 03 C 5) 9 o W O o o 4 4 N Q-d 129 H H CR, OCR, 3-CR3 3-CR, H 0logwishtined 130 , 2-CR, H CR, CR, 3-CR, 3-CR, H CO / \ yellowish-tinged - orange CL CL 131 H \b 3: \b C a 132 CL H H CR, OC,H, 3-CR, C,Re 6-CR3 -C-OC,H3 yellowish-tinged a a Q 0 E | N U I X 133 CL 2-Br H a m a a e U i3 u 3 c; u u c c: c; c; 134 CL 2-CF, H OCR, CR3 V H 6-CR, -C-CR, II m = Ct v v OCIl, CII, 3-CR, o o x x : x 5 s a a v x N :c x es es x Q > o ~ c c9 n n < No. R8 R1 R2 R3 R4 R5 R7 R6 Z
a s c CS 0 V10 CiC C al ~;d d 5, 0cl o 0 W=0 O=0 a a 137 H H CR3 CR, 3-CR, H 5-CR, CflCt3CL reddish-tinged C 3: 3: a 138 2-CR, 5-CR, II CII, 3-CR, C2H3 R -5O Ct X N - orange m a a vO U v v m a a x = ~ EJ U U D O c m D -r O Q x x V N x c9 x c oo o
No.X R1 R2 R3 R4 R5 R7 R6 Z
a a a a b F: c: I c h 4 j: 3 n X o o X t o o X bO ~ObO O t t o" CR, 3-CR, C,Re o -CO-CR, reddish-tinged U X = : ,, H X X X U ,, 2-CR, H CR, X 31 V V V U H H H C2H5 H a a a a a a V V 2-Cl V CR, OCR, UUUUUV V n HO,S-C,R4NR- X on H '5:en xa ,, H xa a U U D x x O x X c c 147 ,, H H H OCR, 3-CR, H H ,, yellowish-tinged orange 148 ,, o X 3: iieceo = x x = x x x x D v : x x o ~ t ^ t m Xo b oo No. X R1 R2 R3 R4 R5 R7 R6 Z
a a a s E 4 m o RO,C,R4l'IR- R R > OCR, o R H -CO-CM3 orange 150 ,, H H CR3 H 3-CR3 H H ,, reddish-tinged u 0 0 151 ,, H H CR, CR, 3-CR, H 6-CR, o ,, H H CR, CR, 3-CR, C2Me H a, 8 8 8 154 ,, 2-Cl H H CR, 3-CR, C3Rs H v 155 ,, 2-Cl 5-Cl H CR, 3-CR, C2R5 H ,, = orange 156 ,, 2-CM, H H CM, H C2Re H ,, reddish-tinged yellow z ,, 2-CM, H OCR, CR, H C,M1 H yellowish-tinged orange N U ''3n3n'oo' u~U uuTj, u a 159 a n H n OCR, CR, H n Ov 160 V V R H CR, NR-COCR, 3-CR, C,Me Vl -CO-CR, z a a a = a a x 5 a Q = x :c D v v x O Q v v x : = = O O O v = :c x x = t m x v x X x a a v v v v :2 x = 3 = es > > > :c x x i t CCN F 0 c7 > 0 es t m \0 > x o o No.X R1 R2 R3 R4 R5 R7 R6 Z
161 RO,S-C2R4NR- H H CR, CR, 3-CR, H H r$d1$ishtined Q ,, H H CR, OC,Rs H C2R5 H ,, yellowish-tinged orange 8 ,, 1 8 CR, OC,Rs 3-CR3 H H I = Il X = = = X = 165 ,, H H H 0C,R 3-CM, C,Re H 166 HO,S-C,R4N-CH, H H CR, CR, 3-CR3 H R , reddish-tinged yellow 167 ,, H H CR, OC,R3 3-CR3 H H ', yellowish-tinged orange 3y 330 d" 3 169 X z V = = X V 3-CR, V VN a a a a a a a U ,, 2-Cl H CR, = v v v yellow 171 ,, H II u u u a XN XN N N a N ' a s a a m x X Ç x D x x x x 172 O H II H CR3 H C2Re D : H u v ÇJ x x v v O O CJ x x = x x x x x x :c :c x x x v x cc x ~ x = : x x cs x 3 a I Xx N X U V O a x x N t m so > oo ss O < N so xo Xo q: v xo vo s Xo F rs > No.X R1 R2 R3 R4 R5 R7 R6 Z
-cr 3 P o S a e 9 6 "M 360 , > n H H H ^ ^ ^ C ' 03 0C4 CR3 o yeow 174 ,, 2-CR, 5-CR, H CR, 3-CR, H 6-CM, 'c" r ,, H ^ ^ ^ Q R03C,R4-N- H H CR, H 3-CR, C2R, H 8 ., 1 3:: x xo x 2-Cl m CR, x 3-CR3 H 5-CR, 179 RO,S-C,114-N- H H CR, CR3 3-CR, H H ,, 'a C4Ha 180 RO,SC4R9-NH- H H CR, H 3-CR, H H X ,, Q X V = X V V = V 182 a 3: 3: H -0-CR, CR, 3-CR, C,Rc H a yellowish-tinged E V 6 V V V V lD C V V 183 ,, 2-CR, H H CR, 3-CR, H H ,, reddish-tinged yellow 184 HO,S-C4R9-N- H H -0-CR, H e C2R3 x x = U U U e u u U U U u V V Q = a U U a s a a x m x x x :: :c = = x 3 = a a x N x x x vl x =1 x N v x u o I ] a I X Z~VN Z~Ut Z Z V ZV 1t n: :c ~ x R VN N N V V ut Jz ca Clm co m a a r O O O ~ w x x x r = e t m sD F oo 08 o o ~ O1 o) or No.X R1 R2 R3 R4 R5 R7 R6 Z
a c, a b ct "M b E E E I E oa eo oo , oo B 1: .E; hg E 6,0 . 0 a, " p- a d 'Ct xo o" 2 x 185 ROcC4Ra-N1 2-Cl 5-CR3 CR, v o o 3-CR, H R 7el1d10ishtined C,R7 186 RO,CR-CR-N- H H CR, CR3 3-CR3 H 6-CR3 I. I n C,Ile U -O 187 RO3O-C,R4-NR H H H CR3 3-CR3 C,Me H -CO-CR, I ,, n a e e v v 189 X NC X m $ t = X X orange 190 ,, 2-Cl H CR3 -OCR, 3-CR3 C2Re 5-CR, z I yellow M,C 192 RO,S-C4R3-N- M R H OCR3 3-CR3 C2H4CN H 3 e" = :: V V ::: V NC V $ = V 193 a, 2-CR3 H CR, OCR, a a H H a V V = = V V V V 6 E o a R0,O-CR-CR-NR- H H CR, CR3 3-CR3 H H " reddish-tinged $ c a a a ~ a U U U a U U a $a CM, 195 RO,0-CH-CR-NR- v H H CM, O C2H5 O ', X s xa C X X X xa a xa v v : :c u v v v x v v x a v v V, V V V V = I w z zx r I n | | = u U u U V VQ O G V O O M a a a a a > a s a O O O O O O O = Y 3 = x x = ur VZ > oO 0\ 0 ^ N v o 00 00 00 00 Cb No. X R1 R2 R3 R4 R5 R7 R6 Z
a -J o b 3 b 3 E 04 . oa or, C , C , c B tiS S W > . H H o CR, > II yellow R,C N CR, x ,, 2-Cl H OCR, H H H " yellowish-tinged u v 8 z , 198 RO,S-C-C-NR- H H CR, CR, H C H H ,' reddish-tinged 2 a II yellow x x v u uD X ,, H H OCR, H X X orange S 110,8-C-C-N- H H H OCR, 3-CR3 H 6-CR3 -CO-CR3 X 6 U v X X X C2Re 201 2-Cl H OC,R5 CR, a a a u v U UU U 202 llO,S-Cll-(CH,),-N- 2-CR, x x II t < ) I I yello' xa xa m = X RO,S-Cll-((l2),-N- H H CR, H 3-CR3 C,He H ,, a = I a v UN a x O v O = O x v x x r x x = X U O1 = = es a I XN a = z ~ X Zl > EJ I X X D a N fi Z C) I X | X oX X a 8 ) > U a ce = 0 i a x x v xc > oo os o ~ N fe os o o o ó No. X R1 R2 R3 R4 R5 R7 R6 Z
3 c Pc c 3 204 F; H- H H CR3 C2He 3-CR, H H -CO-CR, reddish-tinged v X ., H = N s a 206 2-Cl vl vl I " 0 I 0 0 0 U )m ' D a x x 2-OCR, H CR3 so x x = x o CL 209 c" s u" 3: U S, e Y 3: X = U X C~ > X X X (~/ X a m H n CR, 3-CR, H n -CO-CR2-O-CR, V U V V E E s va a NH 212 Il H X 0('R, H = v U yellowish-tinged < orange X t X X X X X ' xa r > v v CR, D 3-CR3 x 6-CR, D reddish-tinged x r ~ ~ x ~ x x ~ x a x x x rll x rq x x x = x $ xb U g t m so > x > o t rz < o o o o o o ~ ~ a I rq r I rs No.X R, R2 R, R4 Re R, R6 /
214 HO- H H CH3 CH3 3-CH, C2Ra 6-CH, -CO-CR, reddish-tinged yellow 215 HO- 2-C1 H OCH, CH, 3-CH, C2R5 5-CH, 216 HO 2-OCH, H CH3 OCH, 3-CH, C,R4-CN 6-CH, -CO-CR3 Example 217.
23.5 g of 3-(N-phenylsulphonylamidosulphonyl)aniline are dissolved in 150 ml of water with 5 g of sodium hydroxide. Thereafter, 5 g of sodium nitrite are added.
The resulting solution is added dropwise to a mixture of 500 g of ice and 50 ml of concentrated hydrochloric acid. The mixture is subsequently stirred at OOC for 2 hours, the excess nitrite is destroyed with amidosulphonic acid, and a solution of 8.8 g of 2,5-dimethylaniline in 100 ml of glacial acetic acid is added dropwise. The pH value is adjusted to about 4 with saturated sodium acetate solution. The dyestuff which has precipitated is filtered off and dried at about 40"C.
6.58 g of the dyestuff described above are stirred in 150 ml of 500o by weight hydrochloric acid and diazotised at room temperature with 1 g of sodium nitrite, dissolved in 10 ml of water. 1.6 g of m-toluidine are dissolved in 50 ml of glacial acetic acid and the solution is added to the diazonium salt solution. The pH is adjusted to about 4 with saturated sodium acetate solution. The dyestuff which has precipitated is filtered off and dried at 400 C.
4.1 g of the disazo dyestuff described above are stirred in 60 ml of acetic anhydride and 20 ml of glacial acetic acid at 1200C for 2 hours. The mixture is allowed to cool to room temperature and the dyestuff, which has precipitated, of the formula
is filtered off.
The dyestuff dyes polyamide fibre material orange.
No. X R1 R2 R3 R4 R5 R7 R6 Z
218 HO H H H H 3-CR, H H -CO-CR3 reddish tinged yellow 219 HO H H CR, CR, 3-CR3 H H " 220 MO H H H H H H H 221 HO H H H CR, 3-CR, H H 222 HO H H CR, CR, 3-CR, H H 223 HO H H OCR, CR, 3-CR3 H czH -CO-CR, yellowish tinged orange 224 HO ll H CR, OCR, 3-CR, H H ,' 225 HO H H v OCR, 3-CR3 H H 226 HO H H H CR, 3-CR, H H -CO-ClI, reddish tinged yellow No. X R1 R2 R3 R4 R5 R7 R6 Z
I v, + I 'E a 3 ' o ', o 3 3 - b 227 HO 2-Cl H I O N ^ I ^ ^ U 3 U 228 HO 2-OCR, H H CR, 3-CR3 H 6-CR, 229 HO 2-CR, 4-CR, 3:: 230 HO 4-OC2R3H H CR, OCR, 3-CR, H H CL 231 HO H CR, CR, 3-CR, C3R4CN H -CO-CR, u HO 4-Cl X H -OCR, 3-0-CR, M u e 3n 233 HO 4-Cl H H -NH-CO-CR, 2-CR, H H " 234 HO 4-Cl H CR, CR, 2-CR, H 6-CR, ,' reddish . X ^ D v .
v X = U SC o Z = = 235 HO 4-Cl H I CR, 3-0-CR, H C) tinged '3:" eo 3=m U C) 0, Q ol O V U U D cS es fS t + t t t t O CX t TOz r " c" N m t v^, No. X R1 R2 R3 R4 R5 R7 R6 Z
1: 8 m P 0 3 3 a b n '3 3 ' a e, o^ 5 S bD 3 Q M a I=j. E: C r d '3 o HO 2-Cl 4-Cl o CR, 3-CR, H H rtindgdeidSh 8 8 I I 237 HO 2-Cl 11 -NIl-CO = = = I tinged CR, orange 238 HO II II H CR, 3-CR, 3: H -CO-C, reddish - tinged yellow 239 110 2-CR, 4-CR3 H CR, 3-CR, H H ,' 240 MO 2-CR3 4-CR, , CR, 3-CM, H .
241 110 2-CR, 4-ClI3 CR, CR, H C,R3 H 242 HO 2-CIl3 4-CR, CR, CR, 3-CR, H 6-CR, eq HO 2-CR3 4-ClI, CR, CII, 3-CR, C2R, H ', U U 2-CR3 4-Cil, OCR, CR, 3-CR, C H ,' yellowish o orange 245 HO 2-CR, 4-Cl U CII, OCR, 3-CR, U 11 -CO o o o o c o o o o o sc F x ch o H eN er m No.X R1 R2 R3 R4 R5 R7 R6 Z
a e a .s 3 -a Y a b) 246 HO 2-CR, 4-CR, CR, > o Li 247 HO 2-CR, 4-CR, CR, CR, 3-0-CR, H H -m X, HO 2-CR, 4-CR, H å yellow 249 HO 2-CR, 4-CR, H CR, 3-CR, H ~ 250 HO N tinged orange U m = HO 3-Cl H CR3 CR, 3-CR, X ::C O U O U U U U yeIlo 252-NH- H H H CR, 3-CR, H ll ,, 253 ,, U H CR, CR, 3-CR, H V D 254 ,, H H OCR, CR, R C,Hs H ,, yellowish tinged V U 1 3 V O U c) U U U v 2 O O O O O O 4 r = v r C vG > X 0E 0 ~ N m t No.X R1 R2 R3 R4 R5 R7 R6 Z
h a .3 h .r: a L: a a C B a .I a 8 v,71 3 U SO-NH- H H CR3 OCR, 3-CR, H 6-CR3 -CO-CR3 yellowish U 8 NC =, t U H H CR, OCR, 3-CM, C2R1 H = X Z 257 ,, H H H OCR3 H H M 'a 258 ,, H M H OCR3 3-CR, H H 'a 259 2-OCR, H CR, C, 3-CR, H M 'a reddish tinged yellow 260 ,, X H CR, CR, 3-CR, H H 261 ,, H H 0CR CR3 3-CM, H H 'a yellowish tinged orange 262 ,, 2-CR, H CR, 0CM3 3-CM, M H a' a, 263 O 2-Cl Q M OCR, H H H 'a a, 264 ,, 2-Cl H H OCR, 3-CR, M H 'a a, 265 CR,-SO,-NR- H H CR, H 3-CR, H H a' reddish 5: x c | = = : x x : 266 C2Hc-S02-NR- H H CR, CR, 3-CR, C,Rc H 'a reddish tinged yellow o U U U NC 5! C X ss X NC > n = = k Z 1 C oN O V U No. X R1 R2 R3 R4 R5 R7 R6 Z
= a b 9 8 ".o o g . s = s n 3 cr 6 = M r 8 1 (d = 267 C,He-SO,NH o H Cur, CR, 3-CR, H H 3n Q u o ,, H ^ = ^ u o 8 co I o u 269 C4Rc-SO,NH H H CR, OCR, 3-CR, CH H 'a o e" z 271 2-OCR, H CR, OC,H3 3-C2H5 H H a' v N N 272 CH,-SO,NH 2-CR, 4-CR, CM, CR, 3-CR, r H U w 5 K rf X lo e K = u Q 2-CR, 4-CR, H Cur, 3-CR, C2R5 b 275 ,, 2-Cl 4-Cl H H 3-CR, H 6-CR, -C0 276 HO3SC2H4NR ,03 u = N N 10 .1 , ,4 " e 277 U H H H CR, V H U U l0 278 ,, 2-Cl H N OCR, CR, 3-OCR, Il H f0 U u 279 llO3S-O-C2ll4NR H U O U U C) = SC 'D = O U U V D U ra m V V Z Z r Z N rt SC C C C U C,) v ~ F oo o ~ > t m Xo F 50 o so qx uO b > rs b > > > > b > No.X R1 R2 R3 R4 R5 R7 R6 Z
c 3 h,, 9 .11 oo 280 HO,S-O-C2H4NH H ll o 281 ,, 2-Br Il CII, CR, 3-CR, CII, H yellow 282 Il 3: 3: 3: 3: S, CM 283 II RC = D V : V L/ L, V H C,Rc 3-CR, CII, H 30 U Z V H Ij CR, V H H H 287 HO; 3: H H ii CR, 3-CR, H V - tinged yellow 288 ,, e r CR3 CR, 3-CR, = H e C: D :: ra ~ rz t = ,|r - Z 4 o ~ N t m so F x r X rl rz rl rl rl rq rs rq No. X R1 R2 R3 R4 R5 R7 R6 Z
I Y h Ca 3 '' -J ", sg 0= 0; 289 H H CR, -OCR, 2-CR, H 6-CR, -CO-CM, reddish I I I ,8 31 OCH5 z U 292 U H Q 3-CR, H II -CO-CR, yellowish e" m ;;e V V V V V 293 ,, rew r < > 1 yellow 294 CM5NH 4-Cl H OC,Re CR, 3-OCR, H H -CO-CM orange I V U 0= t:1 V V D I 295 llO,S-C4R9-N- H H CR, CR, 3-CR, C2R, H -CO-CR, reddish I tinged C2H3 ' 3: 3: V rv = rl W LD C as c rl o. t W) co 0 > o 5 v rq rl eS rl rl rl rA No.X R1 R2 R3 R4 R5 R7 R6 Z
a9 s s M O 0 0 n I s cl C,He yellow 297 H0,C,GeN V CR, CR, 3-CR, H V S 8 Se = ; :: :C ,r N-z R5 N OH W 299 OH H H H CR, 3-CR, H H uN 300 OR H H CR, m 3-CR, H V E V II 302 HO H H OCR, CR, 3-CR, C2Rc H 'a 303 HO 4-Cl H CR, CR, 2-CR, H H yellow 304 HO 4-CR, H R OC2Rc 3-CR, H 6-CR, orange 9LX1n = V e = 3-Cl II C,H5 CR, 3-CM, H V u n t HO 2-Cl 4-Cl CR, CR, 3-CR, C2R3 v COC4Ra Q rs rl V I V V V V N + = 3 = = er q q Z rl u > l N I ~ > ZV C. D e rl Vl A O O z r o O O O O O rq o O s rn t No.X R1 R2 R3 R4 R5 R7 R6 Z
S 5 c o c Q = c o 30 a u* u o o u u 5; HO 4-OCR, X H NRCOCR, M C,R5 H COC4H5 orange 308 -NH- H M CR, CR, 3-CR, H H COCH, yellow V H3C NH X 3: 3: U U O V O = H CR, CR, 3-OCR, H H -OcH3 orange G . m V m E m m m r 3 C; V V t r Z I 4 ox F 00 0e 0 O O n0 No.X R1 R2 R3 R4 R5 R6 Z
311 a 4-Cl H CR, CR, 3-CR, C2H4CN H COCH, yellow U NH 312 C,HcSO,NH H H H CR3 H M H a' 313 C4RcSO,NR H H CII, H 3-CR, H H COOC,R B 'a 314 hO;;NH- R I! H -OCR, 3-CR, M 5-CR, COCH, orange 315 HO -CM\ H H CR OCR, 3-CR, H 6-CR, -CO-CR, yellowish u" NM 316 RO,S-C,R4-NR- H H CR, CR, 2-CR, M H ,, reddish-tinged '3m m 317 HO,S-0-C3H4-NR 4-Cl II CR, CR, 3-CR, H ,, reddish-tinged - yellow
No.A B C R7 Z
a c .O o sl Q 8x 0 - CM3 CM3 yellow I I I N 319 Z tS D e u" e e u" 321 H O a CM3 CM3 322 ,, H a a, CM3 CM3 323 ,, a' ,, H CHCM a' 324 'a C2R4CN -CO-Cl I, a' X CSo O ~ No. A B C R7 Z
b ab . O . .tn .o: ~ .~ o ,C C C E , C C C C C o o n > t ,8 Ma5s-CM/\ CM3 tinged orange 326 ID.5 1C3 H -CO-C, yellowish 505M I orange CM3 CM3 CM3 I CM CM 327 - H COCR, yellowish CC X = X = = = CM3 CM3 328 5I\ ffi\ R 8.P-s - CM3 tinged red CM 329 ,, ,, M )$a "erlglOShg CM3 CL OCH3 NCL F 1 b 7
Claims (14)
1. A dyestuff which contains only one acid group and in the form of the free acid, corresponds to the general formula
in which
p is 0 or 1,
X denotes OH, NH-SO2-R8, N(R9)-alkylene-OSO3H,
N(R9)-alkylene-SO3H, N(R9)-arylene-SO3H,
N(R9)-arylene-CH2-SO3H or N(R9)-arylene-SO2-NH-SO2-R8
Z denotes acyl,
R1 and Re independently denote hydrogen or a non-ionic substituent (as
hereinbefore defined), Re, Re and Re independently denote hydrogen
optionally substituted alkyl, optionally substituted aralkyl, optionally
substituted aryl, halogen, optionally substituted alkoxy, optionally
aryloxy, optionally substituted aralkyloxy or optionally substituted
acylamino or,
R4and R3 together denote the remaining members of a fused benzene
ring.
R@ and R@ denote hydrogen or optionally substituted alkyl,
R7 denotes hydrogen, optionally substituted alkyl, optionally substituted
aryl or optionally substituted aralkyl and R5 denotes optionally
substituted alkyl, optionally substituted aralkyl, optionally substituted
aryl or dialkylamino.
2. A dyestuff according to claim 1, in which P is defined as in claim 1, X
denotes OH, NH-SO2-R5, N(R9)-(C2 to C6)alkylene-OSO3H, N(R9)
(C2 to C6)alkylene-SO3H, N(R@)-phenylene-SO3H, N(R9)-phenylene
CH2-SO3H or N(R9)-phenylene-SO2NH-SO2-R@, wherein the
phenylene may be substituted by C1 to C4 alkyl, C1 to C4 alkoxy, halogen,
cyano or nitro,
R1 and R2 independently denote hydrogen, chlorine or bromine, methyl,
ethyl, methoxy, ethoxy, cyano, trifluoromethyl or phenoxy R3, R4, R5 and Re independently denote hydrogen, or C, to C4 alkyl, C, to C4 alkoxy, (C1 to
C4 alkyl)carbonylamino, benzoylamino, C1 to C4 alkylsulphonylamino, phenylsulphonylamino, (C1 to C4 alkoxy)carbonylamino or
phenoxycarbonylamino, wherein the phenyl nuclei may be substituted by
methyl, ethyl, methoxy, ethoxy, chlorine, bromine or cyano.
R7 denotes hydrogen, C, to C4 alkyl group which is optionally substituted by
chlorine, hydroxyl or cyano, benzyl or phenetbyl, R5 denotes C, to C4 alkyl or phenyl which is optionally substituted by
methyl, chlorine or bromine, denotes hydrogen, methyl or ethyl and Z denotes a (C, to C4
alkyl)carbonyl group which is optionally substituted by cyano, C, to C4
alkoxy, phenoxy or phenyl, benzoyl which is optionally substituted by C, to
C alkyl, chlorine, bromine, nitro, cyano, C, to C4 alkoxy or a C, to C4 altylsulphonyl, phenylsulphonyl, phenoxycarbonyl or C, to C4
alkoxycarbonyl group, wherein the phenyl and phenoxy groups may be
substituted by chlorine, C1 to C4 alkyl, C, to C4 alkoxy or cyano.
3. A dyestuff according to claim 1 which, in the form of the free acid, corresponds to the general formula
in which
Z' denotes C, to C4 alkyl)carbonyl, benzoyl which is optionally
substituted by methyl, methoxy or chlorine, phenylacetyl which is
optionally substituted by methyl, methoxy, or chlorine or phenoxyacetyl
which is optionally substituted by methyl, methoxy or chlorine, X'
denotes OH, NH-SO2-R@', N(R@')-C@ to C@ alkylene-OSO@H.
N(Re')-C2 to C4 alkylene-SO3H or
R1' and R; independently denote hydrogen, methyl, ethyl, chlorine,
bromine or trifluoromethyl, R3 and R4 independently denote hydrogen, methyl, ethyl, methoxy,
ethoxy, acetylamino, methylsulphonylamino or phenylsulphonylamino
R5' denotes hydrogen, methyl, ethyl, methoxy ethoxy or acetylamino
R6' denotes hydrogen or methyl,
R7' denotes hydrogen, methyl, ethyl, 2-cyanoethyl, 2-chloroethyl, benzyl
or phenethyl,
R8' denotes C1 to C4 alkyl or phenyl which is optionally substituted by
methyl, chlorine or bromine and
R9' denotes hydrogen, methyl or ethyl.
4. A dyestuff according to claim 3 which, in the form of the free acid, corresponds to the general formula
in which
X', R, and R6' are defined as in claim 3,
R'2 denotes hydrogen, or methyl,
R3" denotes hydrogen, methyl or methoxy, R'4 denotes hydrogen, methyl, methoxy, ethoxy or acetylamino, R'5 denotes hydrogen, methyl or acetylamino and
Z" denotes acetyl or propionyl, benzoyl which is optionally substituted by
methyl, methoxy or chlorine, phenylacetyl which is optionally substituted
by methyl, methoxy or chlorine, or phenoxyacetyl which is optionally
substituted by methyl, methoxy or chlorine, or phenoxyacetyl which i; optionally substituted by methyl, methoxy or chlorine.
5. A dyestuff according to claim 1, as hereinbefore specifically identified.
6. A process for the production of a dyestuff as claimed in claim 1, in which an aminodisazo dyestuff of the general formula
in which
X, p, R1, R2, R3, R4, R5, R6 and R7 are defined as in claim 1, is acylated.
7. A process according to claim 6, in which the aminodisazo dyestuff of formula (VI) is produced by diazotosing an amino compound of the general formula
in which X, R1, Re Re, Re and p are as defined in claim 1, and coupling with an amine of the general formula
in which RB, Re and R7 are defined as in claim 1.
8. A process according to claim I, when carried out substantially as described in any one of the Examples.
9. A dyestuff as claimed in claim 1, when produced by the process of any of claims 6 to 8.
10. A process for dyeing a natural or synthetic fibre material comprising treating the material with a dyestuff as claimed in any of claims 1 to 3, 5 and 9.
I I. A process according to claim 10, when carried out substantially as described in the "Dyeing Example."
12. A natural or synthetic fibre material when dyed by the process of claim 10 or 11.
13. A process according to claim 10, in which a dyestuff as claimed in claim 4, is used.
14. A natural or synthetic fibre material when dyed by the process of claim 13.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2708779A DE2708779C2 (en) | 1977-03-01 | 1977-03-01 | Disazo dyes, process for their preparation and their use |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1569062A true GB1569062A (en) | 1980-06-11 |
Family
ID=6002451
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB7698/78A Expired GB1569062A (en) | 1977-03-01 | 1978-02-27 | Disazo dyestuffs |
Country Status (8)
Country | Link |
---|---|
JP (1) | JPS53106728A (en) |
BE (1) | BE864333A (en) |
BR (1) | BR7801194A (en) |
DE (1) | DE2708779C2 (en) |
ES (1) | ES467346A1 (en) |
FR (1) | FR2382484A1 (en) |
GB (1) | GB1569062A (en) |
IT (1) | IT7820645A0 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4384870A (en) | 1980-08-08 | 1983-05-24 | Sandoz Ltd. | Disazo compounds having a sulfo group-containing diazo component radical, a 1,4-phenylene middle component radical having a substituted amino group and a coupling component radical having a free, acylated or etherified hydroxy group |
US5183881A (en) * | 1990-09-04 | 1993-02-02 | Bayer Aktiengesellschaft | O-aminoazo compounds |
US5527889A (en) * | 1992-10-26 | 1996-06-18 | Ciba-Geigy Corporation | Disazo dyes containing an alkanoylamino group and a substituted alkoxy group |
US5691459A (en) * | 1995-07-21 | 1997-11-25 | Ciba-Geigy Corporation | Disazo dyes containing two carbonylamino groups processes for their preparation and their use |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1267769B (en) * | 1959-03-13 | 1968-05-09 | Du Pont | Process for the preparation of water-soluble dis- and tetrakis-azo dyes |
BE637176A (en) * | 1963-08-07 | |||
DE1644235C3 (en) * | 1967-11-30 | 1975-01-09 | Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt | Water-soluble disazo dye, process for its preparation and its use |
DE1923680C3 (en) * | 1969-05-09 | 1978-04-20 | Bayer Ag, 5090 Leverkusen | Disazo dyes and their use for dyeing and printing natural and synthetic fiber materials |
DE2006733C3 (en) * | 1970-02-14 | 1979-06-13 | Bayer Ag, 5090 Leverkusen | Disazo dyes containing a sulfo group and their use for dyeing fiber materials made from synthetic polyamides |
US3823131A (en) * | 1971-06-23 | 1974-07-09 | Toms River Chemical Corp | Dialkylamino disazo sulfonic acid dyestuffs |
US3847895A (en) * | 1971-09-30 | 1974-11-12 | Gaf Corp | Substituted sulfophenyl-azo-naphthylazo-anilide compounds |
DE2159216A1 (en) * | 1971-11-30 | 1973-06-14 | Hoechst Ag | NEW HYDRO-SOLUBLE DISAZO DYES AND METHODS FOR THEIR PRODUCTION |
DE2324067A1 (en) * | 1973-05-12 | 1974-11-28 | Bayer Ag | DISAZO DYES |
NL7514577A (en) * | 1974-12-20 | 1976-06-22 | Hoechst Ag | WATER SOLUBLE DISAZO COLORING AGENTS, PREPARATION AND USE. |
-
1977
- 1977-03-01 DE DE2708779A patent/DE2708779C2/en not_active Expired
-
1978
- 1978-02-24 IT IT7820645A patent/IT7820645A0/en unknown
- 1978-02-27 JP JP2105778A patent/JPS53106728A/en active Pending
- 1978-02-27 BE BE185492A patent/BE864333A/en not_active IP Right Cessation
- 1978-02-27 GB GB7698/78A patent/GB1569062A/en not_active Expired
- 1978-02-27 ES ES467346A patent/ES467346A1/en not_active Expired
- 1978-02-28 BR BR7801194A patent/BR7801194A/en unknown
- 1978-02-28 FR FR7805685A patent/FR2382484A1/en active Granted
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4384870A (en) | 1980-08-08 | 1983-05-24 | Sandoz Ltd. | Disazo compounds having a sulfo group-containing diazo component radical, a 1,4-phenylene middle component radical having a substituted amino group and a coupling component radical having a free, acylated or etherified hydroxy group |
US5183881A (en) * | 1990-09-04 | 1993-02-02 | Bayer Aktiengesellschaft | O-aminoazo compounds |
US5527889A (en) * | 1992-10-26 | 1996-06-18 | Ciba-Geigy Corporation | Disazo dyes containing an alkanoylamino group and a substituted alkoxy group |
US5691459A (en) * | 1995-07-21 | 1997-11-25 | Ciba-Geigy Corporation | Disazo dyes containing two carbonylamino groups processes for their preparation and their use |
Also Published As
Publication number | Publication date |
---|---|
BE864333A (en) | 1978-08-28 |
IT7820645A0 (en) | 1978-02-24 |
FR2382484B1 (en) | 1984-01-27 |
JPS53106728A (en) | 1978-09-18 |
DE2708779C2 (en) | 1985-09-05 |
ES467346A1 (en) | 1978-10-16 |
FR2382484A1 (en) | 1978-09-29 |
DE2708779A1 (en) | 1978-09-07 |
BR7801194A (en) | 1978-10-10 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PCNP | Patent ceased through non-payment of renewal fee |