DE1544587A1 - Farbstoff-Eisen-Komplex sowie Verfahren zu seiner Herstellung - Google Patents
Farbstoff-Eisen-Komplex sowie Verfahren zu seiner HerstellungInfo
- Publication number
- DE1544587A1 DE1544587A1 DE19661544587 DE1544587A DE1544587A1 DE 1544587 A1 DE1544587 A1 DE 1544587A1 DE 19661544587 DE19661544587 DE 19661544587 DE 1544587 A DE1544587 A DE 1544587A DE 1544587 A1 DE1544587 A1 DE 1544587A1
- Authority
- DE
- Germany
- Prior art keywords
- dye
- acid
- sulfonamido
- iron
- hydroxy
- 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
- 238000000034 method Methods 0.000 title claims description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 17
- -1 cyano, sulfonamido, N-monosubstituted sulfonamido Chemical group 0.000 claims description 9
- 229940067157 phenylhydrazine Drugs 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 6
- DQIVFTJHYKDOMZ-UHFFFAOYSA-N 96-67-3 Chemical compound NC1=CC([N+]([O-])=O)=CC(S(O)(=O)=O)=C1O DQIVFTJHYKDOMZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000005420 sulfonamido group Chemical class S(=O)(=O)(N*)* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- ALLNAVCIMOJNMN-UHFFFAOYSA-N 4-phenylpyrazol-3-one Chemical compound O=C1N=NC=C1C1=CC=CC=C1 ALLNAVCIMOJNMN-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 239000000975 dye Substances 0.000 description 20
- 239000010985 leather Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 6
- 239000000987 azo dye Substances 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- HXUIDZOMTRMIOE-UHFFFAOYSA-N 3-oxo-3-phenylpropionic acid Chemical compound OC(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- 241000208225 Rhus Species 0.000 description 2
- 235000014220 Rhus chinensis Nutrition 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- MZKALFCNIJHTJG-UHFFFAOYSA-N 2,5-diphenyl-4h-pyrazol-3-one Chemical compound O=C1CC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 MZKALFCNIJHTJG-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- 150000004698 iron complex Chemical class 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000007903 penetration ability Effects 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/22—Monoazo compounds containing other metals
-
- 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
- C09B43/003—Cyclisation of azo dyes; Condensation of azo dyes with formation of ring, e.g. of azopyrazolone dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44061265A | 1965-03-17 | 1965-03-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1544587A1 true DE1544587A1 (de) | 1970-03-19 |
Family
ID=23749470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661544587 Pending DE1544587A1 (de) | 1965-03-17 | 1966-03-01 | Farbstoff-Eisen-Komplex sowie Verfahren zu seiner Herstellung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3423393A (en, 2012) |
| BE (1) | BE677915A (en, 2012) |
| CH (1) | CH478207A (en, 2012) |
| DE (1) | DE1544587A1 (en, 2012) |
| GB (1) | GB1136715A (en, 2012) |
| NL (2) | NL6602993A (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2806950C2 (de) * | 1978-02-18 | 1982-05-19 | Bayer Ag, 5090 Leverkusen | Eisenkomplexazofarbstoffe und deren Verwendung |
| CH670095A5 (en, 2012) * | 1986-04-28 | 1989-05-12 | Sandoz Ag | |
| US5376151A (en) * | 1993-04-16 | 1994-12-27 | North Carolina State University | Environmentally friendly method for producing lightfast black shades on natural and synthetic substrates |
| US5746821A (en) * | 1995-02-13 | 1998-05-05 | Engelhard Corporation | Pigment compositions |
| US5669967A (en) * | 1996-05-30 | 1997-09-23 | Engelhard Corporation | Pigment compositions |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2734895A (en) * | 1956-02-14 | Cochj | ||
| CA642408A (en) * | 1962-06-05 | Buehler Arthur | Cobaltiferous azo-dyestuffs | |
| US1841623A (en) * | 1932-01-19 | Hooo oh | ||
| CA552614A (en) * | 1958-02-04 | Ciba Limited | Cobalt and chromium complexes of monazo dyestuffs | |
| US1844397A (en) * | 1925-08-06 | 1932-02-09 | Gen Aniline Works Inc | Manufacture of dyestuffs containing chromium |
| US1856413A (en) * | 1925-12-23 | 1932-05-03 | Nat Aniline & Chem Co Inc | 1-(3'.4'-dichlor-6'-sulphophenyl)-5-pyrazolones and azo coloring matters derived therefrom |
| US2015429A (en) * | 1933-12-01 | 1935-09-24 | Gen Aniline Works Inc | Azo-dyestuffs |
| US2040368A (en) * | 1934-07-21 | 1936-05-12 | Gen Aniline Works Inc | Azo-dyestuffs containing chromium and process of preparing them |
| US2120799A (en) * | 1935-08-03 | 1938-06-14 | Calco Chemical Co Inc | Metallized orange to brown azo dyes |
| US2421315A (en) * | 1943-06-09 | 1947-05-27 | Du Pont | Chromium complex of monazo pyrazolone |
| US2543691A (en) * | 1946-06-07 | 1951-02-27 | Gen Aniline & Film Corp | Azo dyes as silver halide photographic developing agents |
-
0
- NL NL129886D patent/NL129886C/xx active
-
1965
- 1965-03-17 US US440612A patent/US3423393A/en not_active Expired - Lifetime
-
1966
- 1966-03-01 DE DE19661544587 patent/DE1544587A1/de active Pending
- 1966-03-03 CH CH304066A patent/CH478207A/de not_active IP Right Cessation
- 1966-03-08 NL NL6602993A patent/NL6602993A/xx unknown
- 1966-03-15 GB GB11273/66A patent/GB1136715A/en not_active Expired
- 1966-03-16 BE BE677915D patent/BE677915A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL129886C (en, 2012) | |
| BE677915A (en, 2012) | 1966-09-01 |
| CH478207A (de) | 1969-09-15 |
| GB1136715A (en) | 1968-12-18 |
| US3423393A (en) | 1969-01-21 |
| NL6602993A (en, 2012) | 1966-09-19 |
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