DE2716033A1 - ACID AZO DYES - Google Patents
ACID AZO DYESInfo
- Publication number
- DE2716033A1 DE2716033A1 DE19772716033 DE2716033A DE2716033A1 DE 2716033 A1 DE2716033 A1 DE 2716033A1 DE 19772716033 DE19772716033 DE 19772716033 DE 2716033 A DE2716033 A DE 2716033A DE 2716033 A1 DE2716033 A1 DE 2716033A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- formula
- hydrogen
- blue
- chlorine
- 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.)
- Pending
Links
- 239000000460 chlorine Substances 0.000 claims description 23
- 230000008878 coupling Effects 0.000 claims description 20
- 238000010168 coupling process Methods 0.000 claims description 20
- 238000005859 coupling reaction Methods 0.000 claims description 20
- -1 sulfobenzyl Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000000975 dye Substances 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- 239000004952 Polyamide Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 229920002647 polyamide Polymers 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 238000004043 dyeing Methods 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 239000000987 azo dye Substances 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 12
- 229920002292 Nylon 6 Polymers 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- JRKIPFUQFIXHEA-UHFFFAOYSA-N 3-amino-1,2-benzothiazole-7-sulfonic acid Chemical compound C1=CC=C2C(N)=NSC2=C1S(O)(=O)=O JRKIPFUQFIXHEA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FDXOYIGOUGEQBC-UHFFFAOYSA-N 8-(4-methylanilino)naphthalene-1-sulfonic acid Chemical compound C1=CC(C)=CC=C1NC1=CC=CC2=CC=CC(S(O)(=O)=O)=C12 FDXOYIGOUGEQBC-UHFFFAOYSA-N 0.000 description 1
- 101150028349 COLQ gene Proteins 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
- 125000006598 aminocarbonylamino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004990 dihydroxyalkyl group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- FPUKYOSOAAPHTN-UHFFFAOYSA-N n-[3-(diethylamino)phenyl]acetamide Chemical compound CCN(CC)C1=CC=CC(NC(C)=O)=C1 FPUKYOSOAAPHTN-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 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
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3665—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic ring with two nitrogen atoms
- C09B29/3669—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic ring with two nitrogen atoms from a pyrimidine ring
- C09B29/3673—Barbituric acid and derivatives 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
- C09B29/0081—Isothiazoles or condensed isothiazoles
-
- 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
-
- 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
- C09B29/065—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group containing water solubilizing groups
-
- 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
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
- C09B29/30—Amino naphtholsulfonic acid
-
- 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
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
- C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
- C09B29/3656—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing amino-1,2-diazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
O.Z. 32O.Z. 32
Saure AzofarbstoffeAcid azo dyes
Die Erfindung betrifft Verbindungen, die in Form der freien Säuren der Formel IThe invention relates to compounds which, in the form of the free acids of the formula I
Y SOJi Y SOJi
χ, ι ζ χ , ι ζ
I,I,
N=N-K
entsprechen,N = NK
correspond,
in derin the
X Wasserstoff, Chlor, Brom, Cyan, Nitro, C1- bis C^-Alkyl, C1- bis C^-Alkoxy, C- bis C^-Alkylmercapto, Alkylsulfonyl, Alkylsulfinyl, Alkanoyl, Benzoyl, Carboxyl, Di-C1- bis C^-alkylamino, NHCO-C1-bis Cj,-Alkyl, Hydroxy sulfonyl oder gegebenenfalls substituiertes Carbamoyl oder Sulfamoyl,X hydrogen, chlorine, bromine, cyano, nitro, C 1 - to C ^ -alkyl, C 1 - to C ^ -alkoxy, C- to C ^ -alkyl mercapto, alkylsulfonyl, alkylsulfinyl, alkanoyl, benzoyl, carboxyl, di-C 1 - to C ^ -alkylamino, NHCO-C 1 -bis Cj, -alkyl, hydroxy sulfonyl or optionally substituted carbamoyl or sulfamoyl,
K einen Rest der FormelnNo remainder of the formulas
HO5SHO 5 S
2 V 2 V
8098A2/01898098A2 / 0189
OHOH
(HD-S)(HD-S)
H3C CHH 3 C CH
h$Xh $ X
NHRNHR
oderor
HO3SHO 3 S
H,H,
ι 7ι 7
r'r '
HO R-HO R-
E Wasserstoff, Methyl, Methoxy oder Äthoxy, B2 Wasserstoff, Chlor, Methyl, Äthyl, Benzyl, Sulfobenzyl, Methoxy, E hydrogen, methyl, methoxy or ethoxy, B 2 hydrogen, chlorine, methyl, ethyl, benzyl, sulfobenzyl, methoxy,
Äthoxy, SO H oder Acylamino,
B^ Wasserstoff, C1- bis C -Alkyl, C- oder C,-Hydroxy- oder Dihydroxyalkyl,
Ö-Sulfoäthyl, γ-Sulfopropyl, ß-Cyanäthyl, ß-Hydroxy-Y-chlorpropyl,
C,- bis C.-Alkoxyäthyl, Acetoxyäthyl,Ethoxy, SO H or acylamino,
B ^ hydrogen, C 1 - to C -alkyl, C- or C, -hydroxy- or dihydroxyalkyl, Ö-sulfoethyl, γ-sulfopropyl, ß-cyanoethyl, ß-hydroxy-Y-chloropropyl, C, - to C.- Alkoxyethyl, acetoxyethyl,
• 4• 4
ß-Chloräthy1, y-Amino- oder -Acetylaminopropyl, ß-Carboxyfithyl,
ß-Carbamoyläthyl, Benzyl, Sulfobenzyl, Phenyläthyl, Sulfophenyläthyl
oder Cyclohexyl,
B4 C1- bis C.-Alkyl, C0- oder C,-Hydroxyalkyl, ß-Cyanäthyl, ß-Chlor-ß-Chloräthy1, ß-Amino- or -Acetylaminopropyl, ß-Carboxyfithyl, ß-Carbamoyläthyl, Benzyl, Sulfobenzyl, Phenyläthyl, Sulfophenyläthyl or Cyclohexyl,
B 4 C 1 - to C-alkyl, C 0 - or C, -hydroxyalkyl, ß-cyanoethyl, ß-chlorine
äthyl, C.,- bis C -Alkoxyäthyl, Benzyl oder Sulfobenzyl, > 4ethyl, C., - to C -alkoxyethyl, benzyl or sulfobenzyl, > 4
b5 Amino, Acetylamino, Chloracetylamino, Phenoxyacetylamino, Benzoylamino, Chlorbenzoylamino oder Dichlorbenzoylamino,b5 amino, acetylamino, chloroacetylamino, phenoxyacetylamino, benzoylamino, Chlorobenzoylamino or dichlorobenzoylamino,
B Methyl, Chlormethyl, Phenyl, Chlorphenyl oder Acetylamino, B' C1- bis Cg-Alkyl, Cp- oder C,-Hydroxyalkyl, Phenyl-C,- bis C.-B methyl, chloromethyl, phenyl, chlorophenyl or acetylamino, B 'C 1 - to Cg-alkyl, Cp- or C, -hydroxyalkyl, phenyl-C, - to C.-
Alkyl, Cyclohexyl oder Phenyl, ■ die Zahlen 0, 1 oder 2 und
η die Zahlen 1 oder 2 bedeuten.Alkyl, cyclohexyl or phenyl, ■ the numbers 0, 1 or 2 and
η denote the numbers 1 or 2.
-6--6-
809842/0189809842/0189
Einzelne Reste X sind neben den bereits genannten z. B.: CH , CpH , C3H7, C4K9, CH3S, C2H5-S, C3H7-S, C4H9-S, CH3SO2, C2U5SO2, C4H9SO2, CH3SO , CH3O, C2H5O, C3II7O, C4H9O, N(CH3J2, N(C2U5J2,Individual radicals X are in addition to the z. E.g .: CH, CpH, C 3 H 7 , C 4 K 9 , CH 3 S, C 2 H 5 -S, C 3 H 7 -S, C 4 H 9 -S, CH 3 SO 2 , C 2 U 5 SO 2 , C 4 H 9 SO 2 , CH 3 SO, CH 3 O, C 2 H 5 O, C 3 II 7 O, C 4 H 9 O, N (CH 3 J 2 , N (C 2 U 5 J 2 ,
N(c/Hq)o» CONH , CONIICH , CONHC H1-, CONHC ,H7, CONHC.H , ' 2 5 / ν N ( c / H q) o »CONH, CONIICH, CONHC H 1 -, CONHC, H 7 , CONHC.H, '2 5 / ν
P Π MUP U Π U J PΠNf PTf )P Π MUP U Π U J PΠNf PTf)
C4H9 2^C 4 H 9 2 ^
C0n'~~\ , COlQ) oder CON^Jf-CH2CH OH sowie die entsprechendenC0n '~~ \, COlQ) or CON ^ Jf-CH 2 CH OH and the corresponding
Ji \.Ji \.
Sulfamoylreste und CH7Co, ILC ,CO, nc CO, -■* ,CHCO aier H ,C CO. Sulfamoyl radicals and CH 7 Co, ILC, CO, nc CO, - ■ *, CHCO aier H, C CO.
1 - I '» H1C.,- 11 5 1 - I '»H 1 C., - 11 5
Acylaminoreste R sind beispielsweise C- bis C -Alkylcarbonylamino, das noch durch Chlor, Hydroxy oder Carboxyl substituiert sein kann, gegebenenfalls substituiertes Benzoylamino oder C,- bis C.-Alkyl-Acylamino radicals R are, for example, C to C alkylcarbonylamino, which can be substituted by chlorine, hydroxy or carboxyl, optionally substituted benzoylamino or C, - to C-alkyl
L IL ιL IL ι
aminocarbonylamino, r>owU· k.y^^i ^~-i A^-r^ > i aminocarbonylamino, r> owU · k . y ^^ i ^ ~ -i A ^ -r ^> i
fj ' N J oier Ii T1 | " a' ' O 0fj 'NJ oier Ii T 1 | " a " O 0
Im einzelnen seien beispielsweise aufgeführt: NHCHO, NHCOCH , NHCOC2H5, NHCOC H7, NHCOC4H , NHCOCH 2 5 , NHCOCH0Cl, NHCOCHCl0, NHCOCH0OH, NHCOCH0OCH,, NHCH0CH0COOH NHCOCH=CU-COOh, NHCOC=C-COOH, NHCONH2, NHCONHCH , NHCONHC H ,Examples include: NHCHO, NHCOCH, NHCOC 2 H 5 , NHCOC H 7 , NHCOC 4 H, NHCOCH 2 5 , NHCOCH 0 Cl, NHCOCHCl 0 , NHCOCH 0 OH, NHCOCH 0 OCH ,, NHCH 0 CH 0 COOH NHCOCH = CU-COOh, NHCOC = C-COOH, NHCONH 2 , NHCONHCH, NHCONHC H,
NHCONEC H , NHCOC6H , NHCOC6H Cl, NHCOC6H COOH oder NHCOC6H SO3H.NHCONEC H, NHCOC 6 H , NHCOC 6 H Cl, NHCOC 6 H COOH or NHCOC 6 H SO 3 H.
Einzelne Alkyl- und Alkoxyalkylreste für fi und R sind beispielsweise: CH3, C2H5, C3H7, C4U9, C2H4OCH3, C2II4OC2H5, C2H4OC3H7 Individual alkyl and alkoxyalkyl radicals for fi and R are, for example: CH 3 , C 2 H 5 , C 3 H 7 , C 4 U 9 , C 2 H 4 OCH 3 , C 2 II 4 OC 2 H 5 , C 2 H 4 OC 3 H 7
oder C-H.OC ,IL7.
2 4 4 7 or CH.OC, IL 7 .
2 4 4 7
-J--J-
809842/0189809842/0189
ORIGINAL INSPECTEDORIGINAL INSPECTED
·/ υ...:. ^ μ91· / Υ ...:. ^ μ91
Für R sind neben den bereits einzelnen genannten Resten zu erwähnen:For R, in addition to the individual residues already mentioned, the following should be mentioned:
, C4H9 , C 4 H 9
f% TT /t TT ^% TT rt TT f"1 ΓΤ /^t TJ /*| Tl Al TJ f% T] ^^ ^ f% TT / t TT ^% TT rt TT f "1 ΓΤ / ^ t TJ / * | Tl Al TJ f% T] ^^ ^
0,H1-CH9, C^-H1-C9H., CaU-CE-CH0, C,II C H. oder C,H C Π .0, H 1 -CH 9 , C ^ -H 1 -C 9 H., CaU-CE-CH 0 , C, II C H. or C, HC Π.
CH5 CH 5
Zur Herstellung der Verbindungen der Formel I kann man eine Diazoverbindung
von Aminen der Formel II
Y SO ,HTo prepare the compounds of the formula I, a diazo compound of amines of the formula II can be used
Y SO, H
II.II.
mit einer Kupplungskomponente der Formel IIIwith a coupling component of the formula III
HK III,
umsetzen, X und K haben dabei die angegebenen Bedeutungen.HK III,
implement, X and K have the meanings given.
Von besonderer technischer Bedeutung sind Verbindungen der Formel I aCompounds of the formula I a are of particular industrial importance
N=N-K1 N = NK 1
in derin the
X Wasserstoff, Chlor, Brom, Carboxyl oder Hydroxysulfonyl und K einen Rest der FormelX is hydrogen, chlorine, bromine, carboxyl or hydroxysulfonyl and No remainder of the formula
-b-809842/0189 -b-809842/0189
bedeuten.mean.
N 2 V N 2 V
-X-X
oderor
CZ. 32 491CZ. 32 491
Bevorzugte Reste sind dabei für:Preferred residues are for:
R Wasserstoff, Methyl, Chlor, Acylamino oder SO,H;R is hydrogen, methyl, chlorine, acylamino or SO, H;
R5 und R4 C1- bis C -Alkyl, C^ OH, CH2CHOHCH5,R 5 and R 4 C 1 - to C -alkyl, C ^ OH, CH 2 CHOHCH 5 ,
CH2-CH2-OCOCH3, CH2CH2Cl, CH2CH2CN, CCH 2 -CH 2 -OCOCH 3 , CH 2 CH 2 Cl, CH 2 CH 2 CN, C
CH0CH0OCHx, C0H-OC0H1-, 0,H^NHCOCH7. oder CH0C.H.SO,H; R1 Wasserstoff, Methoxy oder Methyl.CH 0 CH 0 OCH x , C 0 H-OC 0 H 1 -, 0, H ^ NHCOCH 7 . or CH 0 CHSO, H; R 1 is hydrogen, methoxy or methyl.
Bevorzugte Acylaminoreste R sind z. B.: COCH , COCH--OH, COCOOH, COCH2-CH2-COOH.Preferred acylamino radicals R are, for. E.g .: COCH, COCH - OH, COCOOH, COCH 2 -CH 2 -COOH.
Die Farbstoffe der Formel I sind rot bis grünblau und eignen sich insbesondere zum Färben von natürlichen und synthetischen Polyamiden, wie Wolle, Polyamid-6 und -6,6, sowie Pelzen.The dyes of the formula I are red to green-blue and are particularly suitable for dyeing natural and synthetic polyamides, such as wool, polyamide-6 and -6,6, and furs.
Man erhält Färbungen mit sehr guten Echtheiten, von denen die Licht- und Naßechtheiten, wie Wasch-, Wasser-, Schweiß-, Walk- und Seewasserechtheiten hervorzuheben sind. Die Farbstoffe haben zudem eine sehr hohe Farbstärke. Bei den Pelzfärbungen ist die gute Bügelechtheit und Kombinierbarkeit zu Braun- und Schwarztönen hervorzuheben. The dyeings obtained have very good fastness properties, of which the light and wet fastness properties, such as wash, water, perspiration, milled and sea water fastnesses are to be emphasized. The dyes also have a very high color strength. The fur dyeings are easy to iron and can be combined with brown and black tones .
In den folgenden Beispielen beziehen sich die Angaben über Teile und Prozente, sofern nicht anders vermerkt, auf das Gewicht. In the following examples, the data on parts and percentages, unless otherwise stated, are by weight.
809842/0189809842/0189
-9--9-
2J Teile 3-Aminobenzisothiazol-7-sulfonsäure werden in 200 Teilen Wasser mit 4»θ Teilen Ätznatron gelöst und nach Zugabe einer Lösung von 6,9 Teilen Natriumnitrit unter Rühren in eine Mischung aus 200 Tei len Eis und 46,4 Teilen 32 /jiger Salzsäure getropft. Die Suspension des Diazoniumsalzes wird ca. 1 Stunde bei 0 - 5 °C gerührt, worauf man den Nitritüberschuß mit wenig Amidosulfonsäure zerstört. Danach gibt man eine wäßrige Lösung von 21,63 Teilen 3-(N,N-Diäthylamino)-acetylaminobenzol in 100 Teilen Wasser und 11,6 Teilen 32 %iger Salzsäure zu. Nach ca. 15 Minuten langem Rühren wird der pH-Wert mit einer Lösung von 57t5 Teilen Natriumacetat auf 4-5 eingestellt. Las Re ak- tionsgemisch wird bis zum Ende der Kupplung weiter gerührt und der Farbstoff abgesaugt. Nach dem Trocknen bei 70 °C unter vermindertem Druck erhält man ein dunkles Pulver der Formel 2J parts of 3-aminobenzisothiazole-7-sulfonic acid are dissolved in 200 parts of water with 4 » θ parts of caustic soda and, after adding a solution of 6.9 parts of sodium nitrite, with stirring, in a mixture of 200 parts of ice and 46.4 parts of 32 / jiger Hydrochloric acid dripped. The suspension of the diazonium salt is stirred for about 1 hour at 0-5 ° C., after which the excess nitrite is destroyed with a little sulfamic acid. An aqueous solution of 21.63 parts of 3- (N, N-diethylamino) acetylaminobenzene in 100 parts of water and 11.6 parts of 32% strength hydrochloric acid is then added. After stirring for about 15 minutes, the pH is adjusted to 4-5 with a solution of 57-5 parts of sodium acetate. The reaction mixture is stirred further until the coupling has ended and the dye is suctioned off. After drying at 70 ° C. under reduced pressure, a dark powder of the formula is obtained
das sich in Wasser mit rotstichig blauer Farbe löst und auf Polyamid 6, Pelzen, Wolle und Leder rotstichig blaue Färbungen von hohem Echtheitsniveau gibt. which dissolves in water with a reddish blue color and gives reddish blue dyeings with a high level of fastness to polyamide 6, fur, wool and leather.
Analog dem Beispiel 1 werden die in der nachfolgenden Tabelle auf geführten Farbstoffe mit ähnlichen coloristiechen Eigenschaften hergestellt. The products listed in the table below to dyes with similar properties coloristiechen be prepared analogously to Example. 1
-10--10-
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4040
DiazokomponenteDiazo component
Kupplungskomponente Farbton auf Polyamid 6Coupling component color on polyamide 6
SO H SO H
NH9 NH 9
SO1HSO 1 H
NH,NH,
C9II^OCOCH, /24C 9 II ^ OCOCH, / 24
/C2H5/ C 2 H 5
C2H5 C 2 H 5
/C3H7/ C 3 H 7
C5H7 C 5 H 7
N Y- NN Y- N
blaublue
violettviolet
blau, rotstichigblue, reddish
blau, rotstichigblue, reddish
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-11--11-
Nr.No.
DiazokomponenteDiazo component
KupplungskomponenteCoupling component
Farbton auf PolyamidColor on polyamide
1010
1313th
SO ,HSO, H
NH,NH,
CH,CH,
CH OhCH Oh
H3?° C.H H 3? ° CH
/C2H5/ C 2 H 5
NHCOCH2CH2COOhNHCOCH 2 CH 2 COOh
blau, rotstichigblue, reddish
blaublue
blau, rotstichigblue, reddish
blaublue
809842/0189809842/0189
U.Z. 3U.Z. 3
Nr.No.
BiazokomponenteBio component
KupplungskomponenteCoupling component
Farbton auf PolyamidColor on polyamide
/C2H4OCE3/ C 2 H 4 OCE 3
C2E4ClC 2 E 4 Cl
ΛΗ5Λ Η 5
CoH.C00CHa 24 5C o H.C00CH a 24 5
CH,CH,
C2E5 C 2 E 5
ΛΗ5Λ Η 5
°2E5° 2 E 5
NHCOC - CCOOH I ι
Cl ClNHCOC - CCOOH I ι
Cl Cl
blau, rotstichigblue, reddish
blau blau, rotstichigblue blue, reddish tinged
violettviolet
blaublue
8098A2/01898098A2 / 0189
S-S-
ο.ζ. yd 491ο.ζ. yd 491
Hr.Mr.
KupplungskomponenteCoupling component
2323
S03? S0 3?
KRrKRr
HH,HH,
SO, HSO, H
2424
NH,NH,
NHCONH,NHCONH,
HHCOGH2ClHHCOGH 2 Cl
C2H4CONH2 C 2 H 4 CONH 2
blau, rotstichigblue, reddish
▼iolett▼ iolett
blau, rotstichigblue, reddish
809842/0189809842/0189
DiazokomponenteDiazo component
Kupplungskomponente Farbton auf Polyamid 6Coupling component color on polyamide 6
NH,NH,
C9H-OCH, /24 3C 9 H-OCH, / 24 3
C_H.OCH, OCH 2 4 3 C_H.OCH, OCH 2 4 3
C0H-COOH <i 4 C 0 H-COOH <i 4
H1CO U H 1 CO U
NHCOCHNHCOCH
NHCO// \\ SO H NHCO // \\ SO H
π w w H2N N blau, rotstichig π ww H 2 N N blue, tinged red
violettviolet
blau, grünstichigblue, greenish tinge
dunkelblaudark blue
rotRed
809842/0189809842/0189
O. Z. $2 -191OZ $ 2 -191
23 Teile 3-Aminobenzisothiazol-7-sulfonsäure werden analog dem Beispiel 1 diazotiert. Anschließend fügt man zu der Suspension des Diazoniumsalzee eine neutrale Lösung von 30,1 Teilen 1-(4-Toluidino)-naphthalin-8-sulfonsäure in 100 Teilen Wasser zu. Der Ansatz wird dann mit Natriumacetat auf einen pH-Wert von 4-5 eingestellt und bis zum Ende der Kupplung weiter gerührt. Der Farbstoff von der Zusammensetzung23 parts of 3-aminobenzisothiazole-7-sulfonic acid are diazotized analogously to Example 1. A neutral solution of 30.1 parts of 1- (4-toluidino) -naphthalene-8-sulfonic acid in 100 parts of water is then added to the suspension of the diazonium salt. The batch is then adjusted to a pH of 4-5 with sodium acetate and stirred further until the coupling has ended. The dye from the composition
SO3BSO 3 B
ς\ ,γ- So5Hς \ , γ- So 5 H
wird mit 160 Teilen Natriumchlorid ausgesalzen, abgesaugt und bei 70 0C getrocknet. Er färbt Polyamid 6, Wolle sowie Pelz in echten, brillanten, grünstichigen Blautönen. is salted out, suction filtered and dried at 70 0 C with 160 parts of sodium chloride. It dyes polyamide 6, wool and fur in real, brilliant, greenish shades of blue.
Die in der nachfolgenden Tabelle zusammengefaßten Farbstoffe lassen eich nach dem Beispiel 30 darstellen, wobei die Kupplungskomponenten der Beispiele 31 - 40 in verdünnter Salzsäure gelöst werden.The dyes summarized in the table below leave calibrate according to example 30, the coupling components of Examples 31-40 can be dissolved in dilute hydrochloric acid.
-lo--lo-
809842/0189809842/0189
ü.z. 32 491ü.z. 32 491
Nr.No.
DiazokomponenteDiazo component
KupplungskomponenteCoupling component
Farbton auf Polyamid Color on polyamide
NELNEL
NH,NH,
30 H30 H.
rr\rr \
NE,NE,
/C2H40H / C 2 H 4 OH
C2E5 C 2 E 5
C9H-OH /24C 9 H-OH / 24
OH, CB5OH, CB 5
/C2H5/ C 2 H 5
°2H5 NHCOCOOH ° 2 H 5 NHCOCOOH
NHCOCH2OCH3 NHCOCH 2 OCH 3
OCH3 C2H5OCH 3 C 2 H 5
/C2H40H / C 2 H 4 OH
CH3 C2E5CH 3 C 2 E 5
blau, rotstichigblue, reddish
blaublue blaublue blau,rotstichigblue, reddish
8098A2/01898098A2 / 0189
ο.ζ. 32 491ο.ζ. 32 491
MX,MX,
KupplungskomponenteCoupling component
Farbton auf Polyamid Color on polyamide
4343
SO5HSO 5 H
HH,HH,
ΛΗ40Η Λ Η 4 0Η
violettviolet
ClCl
OH IOH I
-N-N
CH2CH-CH2-OHCH 2 CH-CH 2 -OH
blau, rotstichigblue, reddish
fH f H
C4H9 C 4 H 9
'C2H5 'C 2 H 5
MHCOHHC.HQ 4 7MHCOHHC.H Q 4 7
/CH5/ CH 5
SO3H CH3SO 3 H CH 3
/0A/ 0 A
809842/0189809842/0189
Diazokomponente KupplungskomponenteDiazo component coupling component
O.Z. 32 491O.Z. 32 491
Farbton auf PolyamidColor on polyamide
NH,NH,
NH,NH,
NH,NH,
SO ,HSO, H
NH,NH,
OH NHCOCH,OH NHCOCH,
-CH,-CH,
ir50?ir 50 ?
OH NHCO-OH NHCO-
HO SHO S
SO HSO H
HO NHCO-/'HO NHCO- / '
SO HSO H
Cl HO NHCO-& Cl HO NHCO - &
SO5HSO 5 H
SO5H blau, grünstichigSO 5 H blue, greenish tinge
rotstichigreddish
blaublue
blaublue
blau, rotstichigblue, reddish
-19--19-
809842/0189809842/0189
O.Z. $2 491OZ $ 2,491
Diazokomponente Kupplungskomponente Diazo component coupling component
HH,HH,
-N-N
HO5SHO 5 S
NHCOCH,NHCOCH,
OHOH
C2H4OSO5HC 2 H 4 OSO 5 H
OHOH
LCOLCO
SO,!! SO3HSO,!! SO 3 H
OH MHOH MH
SO HSO H
C2H5 blau, rotstichig C 2 H 5 blue, reddish tinged
blaublue
blau, rotstichigblue, reddish blaublue
dunkelblau, rotstichigdark blue, reddish violettviolet
-20--20-
809842/0189809842/0189
Kr.Kr.
DiazokomponenteDiazo component
KupplungskomponenteCoupling component
CZ. 32CZ. 32
SO HSO H
SO H SO H
SO HSO H
blau, rotstichigblue, reddish
η ηη η
-21--21-
809842/0189809842/0189
2Λ2Λ
o.z. yi 491 2716033o. z. yi 491 2716033
23 Teile J-AminobenziBothiazol-Y-sulfonsäure werden wie in Beispiel 1 diazotiert dann fügt man zur Suspension des Diazoniumsalzeβ eine wäßrige salzsäure Lösung von 25 Teilen 3-(N,M-Dihydroxyäthy1amino)-acetylaaino-ϋβηζοΐ hinzu. Nachdem die Kupplung beendet ist, dampft man die FarbetofflÖBung zur Trockne ein. Bas erhaltene Pulver der Formel23 parts of J-aminobenzi-thiazole-Y-sulfonic acid are obtained as in Example 1 diazotized, an aqueous hydrochloric acid solution of 25 parts of 3- (N, M-dihydroxyäthy1amino) -acetylaaino-ϋβηζοΐ is then added to the suspension of the diazonium salts. After the coupling is finished, you steam the Dye solution to dry. Bas obtained powder of the formula
HNCOCH3 C2H40H HNCOCH 3 C 2 H 4 OH
färbt Polyamid 6, Volle sowie Pelz in klaren, echten Dunkelblautönen.dyes polyamide 6, solid and fur in clear, genuine dark blue tones.
Sie in der nachfolgenden Tabelle zusammengefaßten Farbstoffe lassen sich nach dem Beispiel 59 darstellen.You leave the dyes summarized in the table below can be represented according to example 59.
809842/0189809842/0189
u.Z. j5^ ^)I uZ j5 ^ ^) I
Nr.No.
DiazokomponenteDiazo component
KupplungskomponenteCoupling component
SO,HSO, H
NH,NH,
SO HSO H
CHCH
ΛΗ 4 0Η Λ Η 4 0Η
C,H,0H 2 4 C, H, OH 2 4
ΛΗ40Η Λ Η 4 0Η
Cl C2H40H Cl C 2 H 4 OH
/C2H40H / C 2 H 4 OH
OCH.OCH.
C2H4OHC 2 H 4 OH
ClCl
C0H-OH /24C 0 H-OH / 24
OCH,OCH,
HNCOCHHNCOCH
C2H4OHC 2 H 4 OH
blau, rotstichigblue, reddish
violettviolet
blau, rotstichigblue, reddish
blaublue
dunkelblaudark blue
809842/0189809842/0189
O.Z. j52O.Z. j52
Hr. Diazokomponente Kupplungskomponente Mr. Diazo component coupling component
Farbton auf Polyamid 6 Color on polyamide 6
SO HSO H
C_H.0H HNCOCH2Cl2 C_H.0H HNCOCH 2 Cl 2
SO H SO H
CH9-CH-CH,CH 9 -CH-CH,
r ί \ Jr ί \ J
OHOH
Oh2-CH-CH OH Oh 2 -CH-CH OH
blau, rotstichigblue, reddish
violettviolet
SO3HSO 3 H
NH,NH,
0 Wn CH3 0 Wn CH 3
HCH3H CH 3
blaublue
-24--24-
809842/0189809842/0189
o.z. 32 491o.z. 32 491
SO5HSO 5 H
üU-*HüU- * H
NH,NH,
blau, rotstichigblue, reddish
, NHC2H4OH, NHC 2 H 4 OH
NHC6H4CH3(P)NHC 6 H 4 CH 3 (P)
NHCOCHNHCOCH
NHCOC2HNHCOC 2 H
SO3HNHC6H4CH (p)SO 3 HNHC 6 H 4 CH (p)
χ Die Kupplungskomponente wird in der erforderlichen Menge Acetonχ The coupling component is acetone in the required amount
gelöst.solved.
BASF Aktiengesellschaft ■BASF Aktiengesellschaft ■
809842/0189809842/0189
Claims (4)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772716033 DE2716033A1 (en) | 1977-04-09 | 1977-04-09 | ACID AZO DYES |
| IT21636/78A IT1095370B (en) | 1977-04-09 | 1978-03-24 | ACID AZO DYES |
| FR7809681A FR2386585A1 (en) | 1977-04-09 | 1978-03-31 | Acid azo dyes contg. amino-benzothiazole sulphonic acid gps. - for natural and synthetic polyamide(s), pelts, leather etc. |
| JP4134378A JPS53126034A (en) | 1977-04-09 | 1978-04-10 | Acid azo dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772716033 DE2716033A1 (en) | 1977-04-09 | 1977-04-09 | ACID AZO DYES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2716033A1 true DE2716033A1 (en) | 1978-10-19 |
Family
ID=6006079
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772716033 Pending DE2716033A1 (en) | 1977-04-09 | 1977-04-09 | ACID AZO DYES |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS53126034A (en) |
| DE (1) | DE2716033A1 (en) |
| FR (1) | FR2386585A1 (en) |
| IT (1) | IT1095370B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5532342A (en) * | 1992-06-02 | 1996-07-02 | Mitsubishi Chemical Corporation | Azo metal chelate compound |
| US5691458A (en) * | 1996-09-18 | 1997-11-25 | Polaroid Corporation | Benzoisothiazole azo dyes |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4255326A (en) * | 1979-03-30 | 1981-03-10 | Eastman Kodak Company | Nitrogen and/or sulfur containing heterocyclic azo dyes with aniline, tetrahydroquinoline and benzomorpholine couplers having sulfate group |
| JPS58104956A (en) * | 1981-12-18 | 1983-06-22 | Sumitomo Chem Co Ltd | Preparation of azo dye |
| CN111849194B (en) * | 2020-07-27 | 2021-09-17 | 浙江青松轻纺股份有限公司 | Benzisothiazole dye monomer compound, preparation method and application in hydrophobic fiber material dyeing |
| WO2024111572A1 (en) * | 2022-11-25 | 2024-05-30 | 富士フイルム株式会社 | Coloring composition, method for producing colored article, colored article, and kit |
-
1977
- 1977-04-09 DE DE19772716033 patent/DE2716033A1/en active Pending
-
1978
- 1978-03-24 IT IT21636/78A patent/IT1095370B/en active
- 1978-03-31 FR FR7809681A patent/FR2386585A1/en not_active Withdrawn
- 1978-04-10 JP JP4134378A patent/JPS53126034A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5532342A (en) * | 1992-06-02 | 1996-07-02 | Mitsubishi Chemical Corporation | Azo metal chelate compound |
| US5691458A (en) * | 1996-09-18 | 1997-11-25 | Polaroid Corporation | Benzoisothiazole azo dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2386585A1 (en) | 1978-11-03 |
| IT7821636A0 (en) | 1978-03-24 |
| JPS53126034A (en) | 1978-11-02 |
| IT1095370B (en) | 1985-08-10 |
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