GB299331A - Manufacture of azo-dyestuffs and intermediate products - Google Patents
Manufacture of azo-dyestuffs and intermediate productsInfo
- Publication number
- GB299331A GB299331A GB30592/28A GB3059228A GB299331A GB 299331 A GB299331 A GB 299331A GB 30592/28 A GB30592/28 A GB 30592/28A GB 3059228 A GB3059228 A GB 3059228A GB 299331 A GB299331 A GB 299331A
- Authority
- GB
- United Kingdom
- Prior art keywords
- mol
- acid
- cyanuric chloride
- condensation product
- dehydrothiotoluidinesulphonic
- 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
- 239000013067 intermediate product Substances 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 36
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 32
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 abstract 32
- 239000007859 condensation product Substances 0.000 abstract 29
- 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 abstract 18
- 239000000975 dye Substances 0.000 abstract 14
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 abstract 12
- 229920000742 Cotton Polymers 0.000 abstract 11
- 230000008878 coupling Effects 0.000 abstract 7
- 238000010168 coupling process Methods 0.000 abstract 7
- 238000005859 coupling reaction Methods 0.000 abstract 7
- XRTJYEIMLZALBD-UHFFFAOYSA-N 4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound S1C2=CC(C)=CC=C2N=C1C1=CC=C(N)C=C1 XRTJYEIMLZALBD-UHFFFAOYSA-N 0.000 abstract 6
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 abstract 6
- 239000000835 fiber Substances 0.000 abstract 5
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 abstract 5
- 239000000047 product Substances 0.000 abstract 5
- 238000004043 dyeing Methods 0.000 abstract 4
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 abstract 3
- QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 abstract 3
- 239000005749 Copper compound Substances 0.000 abstract 3
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 abstract 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 3
- 239000000980 acid dye Substances 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000001880 copper compounds Chemical class 0.000 abstract 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 abstract 2
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical group CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 abstract 2
- SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 abstract 2
- 229940044174 4-phenylenediamine Drugs 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 241000220317 Rosa Species 0.000 abstract 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 abstract 2
- 150000008049 diazo compounds Chemical class 0.000 abstract 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 2
- 238000006193 diazotization reaction Methods 0.000 abstract 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 abstract 2
- 239000010446 mirabilite Substances 0.000 abstract 2
- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 abstract 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 abstract 2
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 abstract 2
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 abstract 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 abstract 1
- -1 2 : 5-dichloraniline Chemical compound 0.000 abstract 1
- PAYRUJLWNCNPSJ-RALIUCGRSA-N 2,3,4,5,6-pentadeuterioaniline Chemical compound [2H]C1=C([2H])C([2H])=C(N)C([2H])=C1[2H] PAYRUJLWNCNPSJ-RALIUCGRSA-N 0.000 abstract 1
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 abstract 1
- SBOIKGBWVIHNNT-UHFFFAOYSA-N 2-(aminodiazenyl)benzenesulfonic acid Chemical compound NN=NC1=CC=CC=C1S(O)(=O)=O SBOIKGBWVIHNNT-UHFFFAOYSA-N 0.000 abstract 1
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 abstract 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 abstract 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 abstract 1
- SXEBHIMOUHBBOS-UHFFFAOYSA-N 5-chloro-2-phenoxyaniline Chemical compound NC1=CC(Cl)=CC=C1OC1=CC=CC=C1 SXEBHIMOUHBBOS-UHFFFAOYSA-N 0.000 abstract 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 229960004050 aminobenzoic acid Drugs 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 238000006254 arylation reaction Methods 0.000 abstract 1
- 239000000987 azo dye Substances 0.000 abstract 1
- BEHLMOQXOSLGHN-UHFFFAOYSA-N benzenamine sulfate Chemical compound OS(=O)(=O)NC1=CC=CC=C1 BEHLMOQXOSLGHN-UHFFFAOYSA-N 0.000 abstract 1
- 150000001845 chromium compounds Chemical class 0.000 abstract 1
- 239000003086 colorant Substances 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 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 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 150000004992 toluidines Chemical class 0.000 abstract 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
- C09B43/16—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH662592X | 1927-10-22 | ||
| CH299331X | 1927-10-22 | ||
| CH1867451X | 1927-10-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB299331A true GB299331A (en) | 1930-01-22 |
Family
ID=61562921
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB30592/28A Expired GB299331A (en) | 1927-10-22 | 1928-10-22 | Manufacture of azo-dyestuffs and intermediate products |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US1867451A (de) |
| DE (1) | DE538478C (de) |
| FR (1) | FR662592A (de) |
| GB (1) | GB299331A (de) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1041461B (de) * | 1954-11-29 | 1958-10-23 | Ici Ltd | Verfahren zum Faerben und Bedrucken von Cellulosetextilstoffen |
| US4504273A (en) * | 1982-08-25 | 1985-03-12 | Ciba-Geigy Corporation | Reactive dyes, process for their preparation and use thereof |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE745459C (de) * | 1939-07-12 | 1944-04-25 | Chem Ind Basel | Verfahren zur Herstellung von Dis- und Trisazofarbstoffen |
| US2425286A (en) * | 1941-08-30 | 1947-08-05 | American Cyanamid Co | Azo guanamines |
| US2493703A (en) * | 1947-05-20 | 1950-01-03 | American Cyanamid Co | Azo guanamines |
| DE1102317B (de) * | 1956-08-10 | 1961-03-16 | Ciba Geigy | Verfahren zur Herstellung metallhaltiger Monoazofarbstoffe |
| US2873269A (en) * | 1956-09-14 | 1959-02-10 | Ciba Ltd | Monoazo-dyestuffs |
| CH349014A (de) * | 1956-10-29 | 1960-09-30 | Ciba Geigy | Verfahren zur Herstellung neuer Azofarbstoffe |
| US2979498A (en) * | 1957-04-23 | 1961-04-11 | Ici Ltd | New monoazo dyestuffs |
| GB837953A (en) * | 1957-08-23 | 1960-06-15 | Ici Ltd | New monoazo triazine dyestuffs |
-
1928
- 1928-07-26 DE DEG78414D patent/DE538478C/de not_active Expired
- 1928-10-16 US US312928A patent/US1867451A/en not_active Expired - Lifetime
- 1928-10-20 FR FR662592D patent/FR662592A/fr not_active Expired
- 1928-10-22 GB GB30592/28A patent/GB299331A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1041461B (de) * | 1954-11-29 | 1958-10-23 | Ici Ltd | Verfahren zum Faerben und Bedrucken von Cellulosetextilstoffen |
| US4504273A (en) * | 1982-08-25 | 1985-03-12 | Ciba-Geigy Corporation | Reactive dyes, process for their preparation and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR662592A (fr) | 1929-08-08 |
| DE538478C (de) | 1931-11-19 |
| US1867451A (en) | 1932-07-12 |
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