CH624424A5 - Process for the preparation of water-soluble azo dyes derived from 4,4'-diaminobenzanilide - Google Patents
Process for the preparation of water-soluble azo dyes derived from 4,4'-diaminobenzanilide Download PDFInfo
- Publication number
- CH624424A5 CH624424A5 CH166375A CH166375A CH624424A5 CH 624424 A5 CH624424 A5 CH 624424A5 CH 166375 A CH166375 A CH 166375A CH 166375 A CH166375 A CH 166375A CH 624424 A5 CH624424 A5 CH 624424A5
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- coupled
- acid
- mass
- dyes
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 239000000987 azo dye Substances 0.000 title claims abstract description 5
- XPAQFJJCWGSXGJ-UHFFFAOYSA-N 4-amino-n-(4-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=C(N)C=C1 XPAQFJJCWGSXGJ-UHFFFAOYSA-N 0.000 title abstract description 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims abstract description 11
- 230000008878 coupling Effects 0.000 claims abstract description 6
- 238000010168 coupling process Methods 0.000 claims abstract description 6
- 238000005859 coupling reaction Methods 0.000 claims abstract description 6
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229960004889 salicylic acid Drugs 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims description 5
- -1 4,4'-diaminobenzanilide tetra-nitrogen Chemical compound 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 claims description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims description 2
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 2
- 229960001755 resorcinol Drugs 0.000 claims description 2
- 229950000244 sulfanilic acid Drugs 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 239000010949 copper Substances 0.000 claims 1
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 claims 1
- 229940018564 m-phenylenediamine Drugs 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 13
- 239000000203 mixture Substances 0.000 abstract description 11
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000982 direct dye Substances 0.000 abstract description 4
- 239000004952 Polyamide Substances 0.000 abstract description 3
- 239000010985 leather Substances 0.000 abstract description 3
- 229920002647 polyamide Polymers 0.000 abstract description 3
- 244000025254 Cannabis sativa Species 0.000 abstract description 2
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 abstract description 2
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 abstract description 2
- 240000000491 Corchorus aestuans Species 0.000 abstract description 2
- 235000011777 Corchorus aestuans Nutrition 0.000 abstract description 2
- 235000010862 Corchorus capsularis Nutrition 0.000 abstract description 2
- 229920000742 Cotton Polymers 0.000 abstract description 2
- 235000009120 camo Nutrition 0.000 abstract description 2
- 235000005607 chanvre indien Nutrition 0.000 abstract description 2
- 238000009967 direct dyeing Methods 0.000 abstract description 2
- 239000011487 hemp Substances 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 239000004627 regenerated cellulose Substances 0.000 abstract description 2
- 230000002110 toxicologic effect Effects 0.000 abstract description 2
- 231100000027 toxicology Toxicity 0.000 abstract description 2
- 238000006193 diazotization reaction Methods 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 229910001868 water Inorganic materials 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000835 fiber Substances 0.000 description 7
- 235000002639 sodium chloride Nutrition 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 5
- 241001579016 Nanoa Species 0.000 description 3
- 230000027326 copulation Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 206010007134 Candida infections Diseases 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 239000007832 Na2SO4 Substances 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 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 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000000725 suspension Substances 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
- C09B35/64—Higher polyazo dyes, e.g. of the types
-
- 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
-
- 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
-
- 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<
-
- 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
- C09B45/24—Disazo or polyazo compounds
- C09B45/28—Disazo or polyazo compounds containing copper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2038174A IT1007324B (it) | 1974-02-11 | 1974-02-11 | Coloranti azoici idrosolubili deri vati dalla 4.4 diaminobenzanilide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH624424A5 true CH624424A5 (en) | 1981-07-31 |
Family
ID=11166217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH166375A CH624424A5 (en) | 1974-02-11 | 1975-02-10 | Process for the preparation of water-soluble azo dyes derived from 4,4'-diaminobenzanilide |
Country Status (10)
| Country | Link |
|---|---|
| JP (3) | JPS5839181B2 (OSRAM) |
| BE (1) | BE825409A (OSRAM) |
| CA (1) | CA1037029A (OSRAM) |
| CH (1) | CH624424A5 (OSRAM) |
| DE (1) | DE2505188C2 (OSRAM) |
| ES (1) | ES434567A1 (OSRAM) |
| FR (1) | FR2260607B1 (OSRAM) |
| GB (1) | GB1486542A (OSRAM) |
| IT (1) | IT1007324B (OSRAM) |
| NL (1) | NL7501419A (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61203497U (OSRAM) * | 1985-06-10 | 1986-12-20 | ||
| JPH05217083A (ja) * | 1992-02-03 | 1993-08-27 | Adobitsuku:Kk | 赤外線検出器付き警報装置 |
| JP5022744B2 (ja) | 2007-03-13 | 2012-09-12 | 本田技研工業株式会社 | 車両組立装置 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH212995A (de) * | 1938-10-05 | 1940-12-31 | Geigy Ag J R | Verfahren zur Darstellung eines Hexakisazofarbstoffes. |
| US2204230A (en) * | 1939-03-29 | 1940-06-11 | Du Pont | Azo dyes |
| DE849287C (de) * | 1949-07-20 | 1952-09-15 | Ciba Geigy | Verfahren zur Herstellung von Trisazofarbstoffen |
| CH313297A (de) * | 1953-01-30 | 1956-03-31 | Geigy Ag J R | Verfahren zur Herstellung eines braunen Lederfarbstoffes |
| BE795378A (fr) * | 1972-02-15 | 1973-08-13 | Sandoz Sa | Nouveaux colorants polyazoiques et leur preparation |
-
1974
- 1974-02-11 IT IT2038174A patent/IT1007324B/it active
-
1975
- 1975-02-06 NL NL7501419A patent/NL7501419A/xx not_active Application Discontinuation
- 1975-02-07 DE DE19752505188 patent/DE2505188C2/de not_active Expired
- 1975-02-07 GB GB535575A patent/GB1486542A/en not_active Expired
- 1975-02-08 ES ES434567A patent/ES434567A1/es not_active Expired
- 1975-02-10 CA CA219,678A patent/CA1037029A/en not_active Expired
- 1975-02-10 FR FR7504026A patent/FR2260607B1/fr not_active Expired
- 1975-02-10 CH CH166375A patent/CH624424A5/it not_active IP Right Cessation
- 1975-02-10 JP JP1639375A patent/JPS5839181B2/ja not_active Expired
- 1975-02-11 BE BE153254A patent/BE825409A/xx not_active IP Right Cessation
-
1983
- 1983-04-21 JP JP6931283A patent/JPS5945701B2/ja not_active Expired
- 1983-04-21 JP JP6931183A patent/JPS5945700B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5839181B2 (ja) | 1983-08-27 |
| ES434567A1 (es) | 1976-12-01 |
| BE825409A (fr) | 1975-08-11 |
| GB1486542A (en) | 1977-09-21 |
| JPS50110424A (OSRAM) | 1975-08-30 |
| DE2505188A1 (de) | 1975-08-14 |
| JPS5945701B2 (ja) | 1984-11-08 |
| FR2260607A1 (OSRAM) | 1975-09-05 |
| FR2260607B1 (OSRAM) | 1977-04-15 |
| JPS58194956A (ja) | 1983-11-14 |
| NL7501419A (nl) | 1975-08-13 |
| JPS5945700B2 (ja) | 1984-11-08 |
| DE2505188C2 (de) | 1984-02-16 |
| CA1037029A (en) | 1978-08-22 |
| IT1007324B (it) | 1976-10-30 |
| JPS58194955A (ja) | 1983-11-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1923680C3 (de) | Disazofarbstoffe und ihre Verwendung zum Färben und Bedrucken von natürlichen und synthetischen Fasermaterialien | |
| DE892860C (de) | Halogensilberemulsionen fuer das Silber-Azofarbstoff-Ausbleichverfahren | |
| CH624424A5 (en) | Process for the preparation of water-soluble azo dyes derived from 4,4'-diaminobenzanilide | |
| DE2363603A1 (de) | Azofarbstoffe | |
| DE2006261C3 (de) | SulfonsäuregruppenhaJtige Disazofarbstoffe und ihre Verwendung zum Färben und Bedrucken von natürlichen und künstlichen Polyamidfasermaterialien | |
| US3928313A (en) | Trisazo dyestuff | |
| DE2910458A1 (de) | Polyazofarbstoffe | |
| SU489345A3 (ru) | Способ получени полиазосоединени | |
| DE2105935C3 (de) | Disazofarbstoffe und ihre Verwendung zum Färben und Bedrucken von natürlichen und synthetischen Textilfasermaterialien | |
| DE888903C (de) | Verfahren zur Herstellung von aetzbaren Azofarbstoffen | |
| US3729458A (en) | Coupling tetrazotized aromatic diamines with amino hydroxynaphthalenes employing basic inorganic salts of magnesium or lithium | |
| US1000606A (en) | Black trisazo dye. | |
| SU95528A1 (ru) | Способ получени протравных моноазокрасителей | |
| DE842520C (de) | Verfahren zur Herstellung von metallisierbaren Tetrakisazofarbstoffen der Dipyrazolonreihe | |
| US2245517A (en) | Polyazo dyestuffs | |
| US3983101A (en) | Water-soluble polyazo compound derived from 4-4-diaminobenzanilide | |
| KR860000175B1 (ko) | 반응성 직접염료의 제조방법 | |
| SU90664A1 (ru) | Способ получени полиазокрасителей | |
| DE961562C (de) | Verfahren zur Herstellung von Polyazofarbstoffen | |
| DE1921046B2 (de) | Disazofarbstoffe, deren Herstellung und Verwendung | |
| DE2049810C3 (de) | Disazofarbstoffe und ihre Verwendung zum Färben von Fasermaterialien aus synthetischen Polyamiden | |
| DE623838C (OSRAM) | ||
| DE732969C (de) | Verfahren zur Herstellung von Hexakisazofarbstoffen | |
| AT37561B (de) | Verfahren zur Darstellung von sekundären Disazofarbstoffen . | |
| DE1419772A1 (de) | Verfahren zur Herstellung von Azofarbstoffen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |