JPS5820983B2 - トリスアゾセンリヨウノ セイゾウホウ - Google Patents
トリスアゾセンリヨウノ セイゾウホウInfo
- Publication number
- JPS5820983B2 JPS5820983B2 JP3473473A JP3473473A JPS5820983B2 JP S5820983 B2 JPS5820983 B2 JP S5820983B2 JP 3473473 A JP3473473 A JP 3473473A JP 3473473 A JP3473473 A JP 3473473A JP S5820983 B2 JPS5820983 B2 JP S5820983B2
- Authority
- JP
- Japan
- Prior art keywords
- solution
- dye
- coupling
- phenyl
- formula
- 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.)
- Expired
Links
- 239000007983 Tris buffer Substances 0.000 title 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 title 1
- 230000008878 coupling Effects 0.000 claims description 19
- 238000010168 coupling process Methods 0.000 claims description 19
- 238000005859 coupling reaction Methods 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- -1 methyl-substituted phenyl Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 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 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 150000001413 amino acids Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 33
- 239000000975 dye Substances 0.000 description 31
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- 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 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- 239000004952 Polyamide Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229920002647 polyamide Polymers 0.000 description 6
- 235000010288 sodium nitrite Nutrition 0.000 description 6
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000010985 leather Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000003929 acidic solution Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000004043 dyeing Methods 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 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WAVOOWVINKGEHS-UHFFFAOYSA-N 3-(diethylamino)phenol Chemical compound CCN(CC)C1=CC=CC(O)=C1 WAVOOWVINKGEHS-UHFFFAOYSA-N 0.000 description 2
- NDACNGSDAFKTGE-UHFFFAOYSA-N 3-hydroxydiphenylamine Chemical compound OC1=CC=CC(NC=2C=CC=CC=2)=C1 NDACNGSDAFKTGE-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 210000004243 sweat Anatomy 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-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
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
- 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 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- 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 1
- 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 1
- 238000005299 abrasion Methods 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000434 metal complex dye Substances 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- C09B35/465—D being derived from diaminodiarylamine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
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 |
|---|---|
| JPS499534A JPS499534A (enExample) | 1974-01-28 |
| JPS5820983B2 true JPS5820983B2 (ja) | 1983-04-26 |
Family
ID=5840819
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3473473A Expired 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 |
| JP55032809A Expired JPS5855274B2 (ja) | 1972-04-01 | 1980-03-17 | 染色方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55032809A Expired JPS5855274B2 (ja) | 1972-04-01 | 1980-03-17 | 染色方法 |
Country Status (9)
| Country | Link |
|---|---|
| JP (2) | JPS5820983B2 (enExample) |
| BE (1) | BE797576A (enExample) |
| CH (1) | CH582217A5 (enExample) |
| DE (1) | DE2215952B2 (enExample) |
| ES (1) | ES413223A1 (enExample) |
| FR (1) | FR2178964B1 (enExample) |
| GB (1) | GB1359454A (enExample) |
| IT (1) | IT981814B (enExample) |
| NL (1) | NL7304265A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4986425A (enExample) * | 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 GB GB1537173A patent/GB1359454A/en not_active Expired
- 1973-03-30 FR FR7311610A patent/FR2178964B1/fr not_active Expired
- 1973-03-30 CH CH464373A patent/CH582217A5/xx not_active IP Right Cessation
- 1973-03-30 BE BE129479A patent/BE797576A/xx unknown
- 1973-03-30 IT IT2244473A patent/IT981814B/it active
- 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 |
| JPS5855274B2 (ja) | 1983-12-08 |
| IT981814B (it) | 1974-10-10 |
| GB1359454A (en) | 1974-07-10 |
| FR2178964A1 (enExample) | 1973-11-16 |
| JPS499534A (enExample) | 1974-01-28 |
| BE797576A (fr) | 1973-10-01 |
| NL7304265A (enExample) | 1973-10-03 |
| DE2215952B2 (de) | 1978-03-02 |
| JPS55142778A (en) | 1980-11-07 |
| ES413223A1 (es) | 1976-01-01 |
| FR2178964B1 (enExample) | 1977-02-04 |
| CH582217A5 (enExample) | 1976-11-30 |
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