DE2255652A1 - Sulfonierte triazofarbstoffe und verfahren zu ihrer herstellung - Google Patents
Sulfonierte triazofarbstoffe und verfahren zu ihrer herstellungInfo
- Publication number
- DE2255652A1 DE2255652A1 DE19722255652 DE2255652A DE2255652A1 DE 2255652 A1 DE2255652 A1 DE 2255652A1 DE 19722255652 DE19722255652 DE 19722255652 DE 2255652 A DE2255652 A DE 2255652A DE 2255652 A1 DE2255652 A1 DE 2255652A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- formula
- dye
- triazo
- triazo dye
- 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 11
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 70
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 41
- 238000005859 coupling reaction Methods 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 23
- 230000002378 acidificating effect Effects 0.000 claims description 20
- 230000008878 coupling Effects 0.000 claims description 15
- 238000010168 coupling process Methods 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 150000001555 benzenes Chemical class 0.000 claims description 4
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 claims description 3
- 150000001448 anilines Chemical class 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 2
- 239000000987 azo dye Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 60
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 55
- 239000000243 solution Substances 0.000 description 52
- 239000000203 mixture Substances 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 35
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 26
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 21
- -1 alkoxy radical Chemical class 0.000 description 19
- 229920000742 Cotton Polymers 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- 150000008049 diazo compounds Chemical class 0.000 description 15
- 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 15
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 235000010288 sodium nitrite Nutrition 0.000 description 13
- 235000011121 sodium hydroxide Nutrition 0.000 description 12
- 239000011780 sodium chloride Substances 0.000 description 11
- 238000001816 cooling Methods 0.000 description 9
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 8
- 239000000835 fiber Substances 0.000 description 8
- 229940018564 m-phenylenediamine Drugs 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical group NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 7
- XPAQFJJCWGSXGJ-UHFFFAOYSA-N 4-amino-n-(4-aminophenyl)benzamide Chemical class C1=CC(N)=CC=C1NC(=O)C1=CC=C(N)C=C1 XPAQFJJCWGSXGJ-UHFFFAOYSA-N 0.000 description 7
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 7
- 239000010985 leather Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 6
- 210000002268 wool Anatomy 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 229950000244 sulfanilic acid Drugs 0.000 description 5
- 229940018563 3-aminophenol Drugs 0.000 description 4
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 4
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920003043 Cellulose fiber Polymers 0.000 description 3
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 3
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 3
- 239000000982 direct dye Substances 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- LTASFWDWBYFZQQ-UHFFFAOYSA-N 2-amino-5-nitrobenzenesulfonic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O LTASFWDWBYFZQQ-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- INSQMADOBZFAJV-UHFFFAOYSA-N 4,4-diamino-n-phenylcyclohexa-1,5-diene-1-carboxamide Chemical compound C1=CC(N)(N)CC=C1C(=O)NC1=CC=CC=C1 INSQMADOBZFAJV-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 241000872198 Serjania polyphylla Species 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- YOIQWFZSLGRZJX-UHFFFAOYSA-N 2-(diethylamino)phenol Chemical compound CCN(CC)C1=CC=CC=C1O YOIQWFZSLGRZJX-UHFFFAOYSA-N 0.000 description 1
- WAVOOWVINKGEHS-UHFFFAOYSA-N 3-(diethylamino)phenol Chemical compound CCN(CC)C1=CC=CC(O)=C1 WAVOOWVINKGEHS-UHFFFAOYSA-N 0.000 description 1
- QFWZVUKQCBTKID-UHFFFAOYSA-N 4-amino-n-(4-amino-2-chlorophenyl)benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=C(N)C=C1Cl QFWZVUKQCBTKID-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 238000009967 direct dyeing Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 239000000991 leather dye Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/38—Trisazo dyes ot the type
- C09B35/44—Trisazo dyes ot the type the component K being a hydroxy amine
- C09B35/46—Trisazo dyes ot the type the component K being a hydroxy amine the component K being an amino naphthol
- C09B35/467—D being derived from diaminodiaryl linked through CON<, SO2N<, CSN<
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Synthetic Leather, Interior Materials Or Flexible Sheet Materials (AREA)
- Paper (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3121271A IT940650B (it) | 1971-11-17 | 1971-11-17 | Coloranti trisazoici idrosolubili e loro preparazione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2255652A1 true DE2255652A1 (de) | 1973-05-24 |
Family
ID=11233287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722255652 Pending DE2255652A1 (de) | 1971-11-17 | 1972-11-14 | Sulfonierte triazofarbstoffe und verfahren zu ihrer herstellung |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE791567A (enExample) |
| CA (1) | CA977748A (enExample) |
| CH (1) | CH606315A5 (enExample) |
| DE (1) | DE2255652A1 (enExample) |
| ES (1) | ES408644A1 (enExample) |
| FR (1) | FR2160473B1 (enExample) |
| GB (1) | GB1417428A (enExample) |
| IT (1) | IT940650B (enExample) |
| NL (1) | NL7215344A (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2306768A1 (de) * | 1972-02-15 | 1973-08-23 | Sandoz Ag | Polyazoverbindungen, ihre herstellung und verwendung |
| DE2504068A1 (de) * | 1974-02-04 | 1975-08-07 | Acna | Triazo-farbstoff und verfahren zu seiner herstellung |
| US4624708A (en) * | 1985-04-15 | 1986-11-25 | Xerox Corporation | Sulfonated trisazo dyes for ink jet compositions |
| US4793860A (en) * | 1986-04-02 | 1988-12-27 | Ricoh Company, Ltd. | Aqueous ink composition |
| EP0449250A1 (en) * | 1990-03-28 | 1991-10-02 | Sumitomo Chemical Company, Limited | Trisazo compounds and use thereof |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN163247B (enExample) * | 1985-08-16 | 1988-08-27 | Atul Products Ltd | |
| IN163246B (enExample) * | 1985-08-16 | 1988-08-27 | Atul Products Ltd | |
| ES2130240T3 (es) * | 1992-02-28 | 1999-07-01 | Ciba Geigy Ag | Procedimiento para teñir cuero con mezclas de colorantes. |
| ES2098709T3 (es) * | 1992-06-30 | 1997-05-01 | Ciba Geigy Ag | Procedimiento para teñir cuero por tricromia con mezclas de colorantes. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB338111A (en) * | 1929-07-03 | 1930-11-03 | Ici Ltd | Improvements in the dyeing of regenerated cellulose materials |
| FR892914A (fr) * | 1940-10-10 | 1944-05-24 | Ig Farbenindustrie Ag | Procédé de production de colorants polyazoïques asymétriques |
| CH314329A (de) * | 1953-03-10 | 1956-06-15 | Ciba Geigy | Verfahren zur Herstellung direktziehender Azofarbstoffe |
-
0
- BE BE791567D patent/BE791567A/xx unknown
-
1971
- 1971-11-17 IT IT3121271A patent/IT940650B/it active
-
1972
- 1972-11-13 CH CH1664972A patent/CH606315A5/xx not_active IP Right Cessation
- 1972-11-13 NL NL7215344A patent/NL7215344A/xx not_active Application Discontinuation
- 1972-11-14 DE DE19722255652 patent/DE2255652A1/de active Pending
- 1972-11-15 FR FR7240488A patent/FR2160473B1/fr not_active Expired
- 1972-11-16 GB GB5303372A patent/GB1417428A/en not_active Expired
- 1972-11-16 CA CA156,677A patent/CA977748A/en not_active Expired
- 1972-11-16 ES ES408644A patent/ES408644A1/es not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2306768A1 (de) * | 1972-02-15 | 1973-08-23 | Sandoz Ag | Polyazoverbindungen, ihre herstellung und verwendung |
| DE2504068A1 (de) * | 1974-02-04 | 1975-08-07 | Acna | Triazo-farbstoff und verfahren zu seiner herstellung |
| US4624708A (en) * | 1985-04-15 | 1986-11-25 | Xerox Corporation | Sulfonated trisazo dyes for ink jet compositions |
| US4793860A (en) * | 1986-04-02 | 1988-12-27 | Ricoh Company, Ltd. | Aqueous ink composition |
| EP0449250A1 (en) * | 1990-03-28 | 1991-10-02 | Sumitomo Chemical Company, Limited | Trisazo compounds and use thereof |
| US5180817A (en) * | 1990-03-28 | 1993-01-19 | Sumitomo Chemical Company, Limited | Trisazo compounds and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1417428A (en) | 1975-12-10 |
| FR2160473B1 (enExample) | 1976-07-23 |
| NL7215344A (enExample) | 1973-05-21 |
| CA977748A (en) | 1975-11-11 |
| IT940650B (it) | 1973-02-20 |
| ES408644A1 (es) | 1975-11-01 |
| BE791567A (fr) | 1973-05-17 |
| FR2160473A1 (enExample) | 1973-06-29 |
| CH606315A5 (enExample) | 1978-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal | ||
| OI | Miscellaneous see part 1 |