DE2215952B2 - Trisazofarbstoffe und deren Verwendung zum Färben von Leder - Google Patents
Trisazofarbstoffe und deren Verwendung zum Färben von LederInfo
- Publication number
- DE2215952B2 DE2215952B2 DE19722215952 DE2215952A DE2215952B2 DE 2215952 B2 DE2215952 B2 DE 2215952B2 DE 19722215952 DE19722215952 DE 19722215952 DE 2215952 A DE2215952 A DE 2215952A DE 2215952 B2 DE2215952 B2 DE 2215952B2
- Authority
- DE
- Germany
- Prior art keywords
- solution
- dye
- trisazo dyes
- acid
- coupling
- 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.)
- Ceased
Links
- 239000000975 dye Substances 0.000 title claims description 25
- 239000010985 leather Substances 0.000 title description 8
- 238000004043 dyeing Methods 0.000 title description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical group [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 230000008878 coupling Effects 0.000 description 12
- 238000010168 coupling process Methods 0.000 description 12
- 238000005859 coupling reaction Methods 0.000 description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
- 235000010288 sodium nitrite Nutrition 0.000 description 6
- 239000003929 acidic solution Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- VKURVCNKVWKGLX-UHFFFAOYSA-N 5-amino-2-(4-aminoanilino)benzenesulfonic acid Chemical compound C1=CC(N)=CC=C1NC1=CC=C(N)C=C1S(O)(=O)=O VKURVCNKVWKGLX-UHFFFAOYSA-N 0.000 description 4
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 3
- SUHWXARLXCIBFK-UHFFFAOYSA-N 3-(2-methylanilino)phenol Chemical compound CC1=CC=CC=C1NC1=CC=CC(O)=C1 SUHWXARLXCIBFK-UHFFFAOYSA-N 0.000 description 3
- -1 alkyl radicals Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
- 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
- WAVOOWVINKGEHS-UHFFFAOYSA-N 3-(diethylamino)phenol Chemical compound CCN(CC)C1=CC=CC(O)=C1 WAVOOWVINKGEHS-UHFFFAOYSA-N 0.000 description 2
- SJCTXIKOXTUQHC-UHFFFAOYSA-N 4-amino-2,5-dichlorobenzenesulfonic acid Chemical compound NC1=CC(Cl)=C(S(O)(=O)=O)C=C1Cl SJCTXIKOXTUQHC-UHFFFAOYSA-N 0.000 description 2
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229940018564 m-phenylenediamine Drugs 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LXQOQPGNCGEELI-UHFFFAOYSA-N 2,4-dinitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O LXQOQPGNCGEELI-UHFFFAOYSA-N 0.000 description 1
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
- MXUKTFBCWISLPC-UHFFFAOYSA-N 2-(3-aminoanilino)acetic acid Chemical compound NC1=CC=CC(NCC(O)=O)=C1 MXUKTFBCWISLPC-UHFFFAOYSA-N 0.000 description 1
- MGCGMYPNXAFGFA-UHFFFAOYSA-N 2-amino-5-nitrobenzonitrile Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C#N MGCGMYPNXAFGFA-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- MESJRHHDBDCQTH-UHFFFAOYSA-N 3-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC(O)=C1 MESJRHHDBDCQTH-UHFFFAOYSA-N 0.000 description 1
- YGOFNNAZFZYNIX-UHFFFAOYSA-N 3-N-phenylbenzene-1,2,3-triamine Chemical compound NC=1C(=C(C=CC1)NC1=CC=CC=C1)N YGOFNNAZFZYNIX-UHFFFAOYSA-N 0.000 description 1
- NDACNGSDAFKTGE-UHFFFAOYSA-N 3-hydroxydiphenylamine Chemical compound OC1=CC=CC(NC=2C=CC=CC=2)=C1 NDACNGSDAFKTGE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- C09B35/465—D being derived from diaminodiarylamine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722215952 DE2215952B2 (de) | 1972-04-01 | 1972-04-01 | Trisazofarbstoffe und deren Verwendung zum Färben von Leder |
| NL7304265A NL7304265A (en, 2012) | 1972-04-01 | 1973-03-27 | |
| JP3473473A JPS5820983B2 (ja) | 1972-04-01 | 1973-03-28 | トリスアゾセンリヨウノ セイゾウホウ |
| CH464373A CH582217A5 (en, 2012) | 1972-04-01 | 1973-03-30 | |
| BE129479A BE797576A (fr) | 1972-04-01 | 1973-03-30 | Colorants trisazoiques et leur obtention |
| GB1537173A GB1359454A (en) | 1972-04-01 | 1973-03-30 | Trisazo dyestuffs |
| IT2244473A IT981814B (it) | 1972-04-01 | 1973-03-30 | Coloranti tris azoici |
| FR7311610A FR2178964B1 (en, 2012) | 1972-04-01 | 1973-03-30 | |
| ES413223A ES413223A1 (es) | 1972-04-01 | 1973-03-31 | Procedimiento para la obtencion de colorantes trisazoicos. |
| JP55032809A JPS5855274B2 (ja) | 1972-04-01 | 1980-03-17 | 染色方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722215952 DE2215952B2 (de) | 1972-04-01 | 1972-04-01 | Trisazofarbstoffe und deren Verwendung zum Färben von Leder |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2215952A1 DE2215952A1 (de) | 1973-10-11 |
| DE2215952B2 true DE2215952B2 (de) | 1978-03-02 |
Family
ID=5840819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722215952 Ceased DE2215952B2 (de) | 1972-04-01 | 1972-04-01 | Trisazofarbstoffe und deren Verwendung zum Färben von Leder |
Country Status (9)
| Country | Link |
|---|---|
| JP (2) | JPS5820983B2 (en, 2012) |
| BE (1) | BE797576A (en, 2012) |
| CH (1) | CH582217A5 (en, 2012) |
| DE (1) | DE2215952B2 (en, 2012) |
| ES (1) | ES413223A1 (en, 2012) |
| FR (1) | FR2178964B1 (en, 2012) |
| GB (1) | GB1359454A (en, 2012) |
| IT (1) | IT981814B (en, 2012) |
| NL (1) | NL7304265A (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4986425A (en, 2012) * | 1972-12-23 | 1974-08-19 | ||
| DE3134063A1 (de) * | 1981-08-28 | 1983-03-10 | Cassella Ag, 6000 Frankfurt | Wasserloesliche polyazofarbstoffe, ihre herstellung und ihre verwendung |
| EP0169808A3 (en) * | 1984-07-24 | 1988-12-21 | Ciba-Geigy Ag | Uv-absorber compounds, method for their preparation and their use as image dyes in photographic materials for the silver dye-bleaching process |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR804316A (fr) * | 1935-04-09 | 1936-10-21 | Ig Farbenindustrie Ag | Procédé pour préparer des colorants azoïques |
| FR1097549A (fr) * | 1953-04-04 | 1955-07-06 | Cassella Farbwerke Mainkur Ag | Colorants trisazoïques et polyazoïques et leur procédé de préparation |
-
1972
- 1972-04-01 DE DE19722215952 patent/DE2215952B2/de not_active Ceased
-
1973
- 1973-03-27 NL NL7304265A patent/NL7304265A/xx not_active Application Discontinuation
- 1973-03-28 JP JP3473473A patent/JPS5820983B2/ja not_active Expired
- 1973-03-30 IT IT2244473A patent/IT981814B/it active
- 1973-03-30 GB GB1537173A patent/GB1359454A/en not_active Expired
- 1973-03-30 CH CH464373A patent/CH582217A5/xx not_active IP Right Cessation
- 1973-03-30 FR FR7311610A patent/FR2178964B1/fr not_active Expired
- 1973-03-30 BE BE129479A patent/BE797576A/xx unknown
- 1973-03-31 ES ES413223A patent/ES413223A1/es not_active Expired
-
1980
- 1980-03-17 JP JP55032809A patent/JPS5855274B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2215952A1 (de) | 1973-10-11 |
| IT981814B (it) | 1974-10-10 |
| FR2178964A1 (en, 2012) | 1973-11-16 |
| JPS55142778A (en) | 1980-11-07 |
| JPS5820983B2 (ja) | 1983-04-26 |
| CH582217A5 (en, 2012) | 1976-11-30 |
| FR2178964B1 (en, 2012) | 1977-02-04 |
| ES413223A1 (es) | 1976-01-01 |
| BE797576A (fr) | 1973-10-01 |
| GB1359454A (en) | 1974-07-10 |
| NL7304265A (en, 2012) | 1973-10-03 |
| JPS499534A (en, 2012) | 1974-01-28 |
| JPS5855274B2 (ja) | 1983-12-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2215952B2 (de) | Trisazofarbstoffe und deren Verwendung zum Färben von Leder | |
| EP0016975B1 (de) | Polyazofarbstoffe sowie ihre Verwendung zum Färben von amino- und hydroxygruppenhaltigen Fasermaterialien und Leder | |
| DE2346462A1 (de) | Wasserloesliche pentakis-azofarbstoffe | |
| DE2347551C3 (de) | Trisazoverbindungen, Verfahren zu deren Herstellung und ihre Verwendung zum Färben von Papier und Leder | |
| DE2140864A1 (de) | Disazofarbstoffe | |
| DE2617302C3 (de) | Verfahren zur Herstellung von Disazofarbstoffen | |
| DE927041C (de) | Verfahren zur Herstellung von Polyazofarbstoffen | |
| DE2306768C2 (de) | Polyazoverbindungen, ihre Herstellung und Verwendung | |
| DE1292277B (de) | Verfahren zur Herstellung von Polyazofarbstoffen | |
| DE677664C (de) | Verfahren zur Herstellung von Polyazofarbstoffen | |
| DE822587C (de) | Verfahren zur Herstellung von Trisazofarbstoffen | |
| DE870147C (de) | Verfahren zur Herstellung von Dis- und Polyazofarbstoffen | |
| DE2302716C3 (de) | Disazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Färbung von Leder | |
| DE289107C (en, 2012) | ||
| DE909383C (de) | Verfahren zur Herstellung von Monoazofarbstoffen | |
| DE2503654C2 (de) | Neuer sulfonierter Triazofarbstoff | |
| DE853188C (de) | Verfahren zur Herstellung von Mono-, Dis- oder Polyazofarbstoffen | |
| DE957507C (de) | Verfahren zur Herstellung von chromhaltigen Azofarbstoffen | |
| DE1769175B2 (de) | Wasserlösliche Polyazofarbstoffe, Verfahren zu ihrer Herstellung und deren Verwendung | |
| DE610625C (de) | Verfahren zur Herstellung faerbender Umwandlungsprodukte von Azofarbstoffen | |
| DE818670C (de) | Verfahren zur Herstellung von Trisazofarbstoffen | |
| DE1932826A1 (de) | Azofarbstoff und Verfahren zu dessen Herstellung | |
| DE956794C (de) | Verfahren zur Herstellung von metallisierbaren Polyazofarbstoffen bzw. deren Metallkomplexverbindungen | |
| DE99468C (en, 2012) | ||
| DE116640C (en, 2012) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8235 | Patent refused |