DE2363603A1 - Azofarbstoffe - Google Patents
AzofarbstoffeInfo
- Publication number
- DE2363603A1 DE2363603A1 DE19732363603 DE2363603A DE2363603A1 DE 2363603 A1 DE2363603 A1 DE 2363603A1 DE 19732363603 DE19732363603 DE 19732363603 DE 2363603 A DE2363603 A DE 2363603A DE 2363603 A1 DE2363603 A1 DE 2363603A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- hydrogen
- formula
- acid
- compound
- 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.)
- Withdrawn
Links
- 239000000975 dye Substances 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- -1 monoazo compound Chemical class 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000987 azo dye Substances 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- ZUQOBHTUMCEQBG-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 ZUQOBHTUMCEQBG-UHFFFAOYSA-N 0.000 claims 1
- QEZZCWMQXHXAFG-UHFFFAOYSA-N 8-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1 QEZZCWMQXHXAFG-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000003086 colorant Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 5
- 229940018564 m-phenylenediamine Drugs 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 3
- 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
- 239000012267 brine Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 235000011837 pasties Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-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 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
- UCGZNHXYVJOCMV-UHFFFAOYSA-N 2-amino-2-(3-aminophenyl)acetic acid Chemical compound OC(=O)C(N)C1=CC=CC(N)=C1 UCGZNHXYVJOCMV-UHFFFAOYSA-N 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
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- CQXXYOLFJXSRMT-UHFFFAOYSA-N 5-diazocyclohexa-1,3-diene Chemical compound [N-]=[N+]=C1CC=CC=C1 CQXXYOLFJXSRMT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- VGCGYVHOTSGFBE-UHFFFAOYSA-L disodium 4-amino-3-[(4-aminophenyl)diazenyl]-5-oxido-6-phenyldiazenyl-7-sulfonaphthalene-2-sulfonate Chemical compound [Na+].[Na+].Nc1ccc(cc1)N=Nc1c(N)c2c(O)c(N=Nc3ccccc3)c(cc2cc1S([O-])(=O)=O)S([O-])(=O)=O VGCGYVHOTSGFBE-UHFFFAOYSA-L 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004519 manufacturing process Methods 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
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/28—Colorants ; Pigments or opacifying agents
-
- 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
- C09B35/461—D being derived from diaminobenzene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Coloring (AREA)
- Color Printing (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5910372A GB1465889A (en) | 1972-12-21 | 1972-12-21 | Trisazo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2363603A1 true DE2363603A1 (de) | 1974-06-27 |
Family
ID=10483070
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732363603 Withdrawn DE2363603A1 (de) | 1972-12-21 | 1973-12-20 | Azofarbstoffe |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE809026A (cs) |
| CH (1) | CH586264A5 (cs) |
| DE (1) | DE2363603A1 (cs) |
| FR (1) | FR2211510B1 (cs) |
| GB (1) | GB1465889A (cs) |
| IT (1) | IT1009076B (cs) |
| NL (1) | NL7317397A (cs) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4141889A (en) * | 1976-08-02 | 1979-02-27 | Sandoz Ltd. | Symmetrical hexakisazo compounds having a 2,2'-disulfostilbenyl central radical |
| US4468348A (en) * | 1972-09-26 | 1984-08-28 | Sandoz Ltd. | Trisazo dyes having a 4-(1-amino-3,6-disulfo-8-hydroxy-7-phenylazonaphthyl-2-azo)phenylazo group linked to a coupling component radical |
| US4734489A (en) * | 1985-03-29 | 1988-03-29 | Taoka Chemical Company, Limited | Trisazo compounds useful in producing water-resistant ink compositions |
| US5258505A (en) * | 1991-07-26 | 1993-11-02 | Canon Kabushiki Kaisha | Trisazo compounds, and dye compositions containing same |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH588535A5 (cs) * | 1974-06-17 | 1977-06-15 | Sandoz Ag | |
| US3963047A (en) * | 1975-09-17 | 1976-06-15 | Caterpillar Tractor Co. | Fill and relief valve arrangement |
| DE2903588A1 (de) * | 1979-01-31 | 1980-08-14 | Basf Ag | Polyazofarbstoffe |
| JPS55108477A (en) * | 1979-02-15 | 1980-08-20 | Pentel Kk | Aqueous black ink |
| JPS60166347A (ja) * | 1984-02-09 | 1985-08-29 | Taoka Chem Co Ltd | 染料溶液組成物 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE582399C (de) * | 1931-06-19 | 1933-08-14 | Chem Fab Vorm Sandoz | Verfahren zur Herstellung von Trisazofarbstoffen |
| DE711386C (de) * | 1935-10-25 | 1941-09-30 | Ig Farbenindustrie Ag | Verfahren zur Herstellung von Polyazofarbstoffen |
| FR1038894A (fr) * | 1950-07-05 | 1953-10-02 | Ici Ltd | Matières colorantes triazoïques nouvelles |
| FR1123473A (fr) * | 1954-05-05 | 1956-09-21 | Cassella Farbwerke Mainkur Ag | Colorants poly-azoïques et leur fabrication |
-
1972
- 1972-12-21 GB GB5910372A patent/GB1465889A/en not_active Expired
-
1973
- 1973-12-19 NL NL7317397A patent/NL7317397A/xx not_active Application Discontinuation
- 1973-12-20 FR FR7345716A patent/FR2211510B1/fr not_active Expired
- 1973-12-20 DE DE19732363603 patent/DE2363603A1/de not_active Withdrawn
- 1973-12-21 BE BE139212A patent/BE809026A/xx unknown
- 1973-12-21 IT IT7082373A patent/IT1009076B/it active
- 1973-12-21 CH CH1810173A patent/CH586264A5/xx not_active IP Right Cessation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4468348A (en) * | 1972-09-26 | 1984-08-28 | Sandoz Ltd. | Trisazo dyes having a 4-(1-amino-3,6-disulfo-8-hydroxy-7-phenylazonaphthyl-2-azo)phenylazo group linked to a coupling component radical |
| US4141889A (en) * | 1976-08-02 | 1979-02-27 | Sandoz Ltd. | Symmetrical hexakisazo compounds having a 2,2'-disulfostilbenyl central radical |
| US4734489A (en) * | 1985-03-29 | 1988-03-29 | Taoka Chemical Company, Limited | Trisazo compounds useful in producing water-resistant ink compositions |
| US5258505A (en) * | 1991-07-26 | 1993-11-02 | Canon Kabushiki Kaisha | Trisazo compounds, and dye compositions containing same |
Also Published As
| Publication number | Publication date |
|---|---|
| CH586264A5 (cs) | 1977-03-31 |
| FR2211510B1 (cs) | 1977-08-12 |
| IT1009076B (it) | 1976-12-10 |
| FR2211510A1 (cs) | 1974-07-19 |
| BE809026A (fr) | 1974-06-21 |
| GB1465889A (en) | 1977-03-02 |
| NL7317397A (cs) | 1974-06-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |