DE1086366B - Verfahren zur Herstellung von Monoazofarbstoffen - Google Patents
Verfahren zur Herstellung von MonoazofarbstoffenInfo
- Publication number
- DE1086366B DE1086366B DEC16398A DEC0016398A DE1086366B DE 1086366 B DE1086366 B DE 1086366B DE C16398 A DEC16398 A DE C16398A DE C0016398 A DEC0016398 A DE C0016398A DE 1086366 B DE1086366 B DE 1086366B
- Authority
- DE
- Germany
- Prior art keywords
- formula
- dyes
- sulfonic acid
- parts
- dye
- 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.)
- Pending
Links
- 239000000975 dye Substances 0.000 title claims description 31
- 238000000034 method Methods 0.000 title claims description 18
- 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 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 claims description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 230000007935 neutral effect Effects 0.000 claims description 5
- 229920000742 Cotton Polymers 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- 210000002268 wool Anatomy 0.000 claims description 4
- -1 3-chloropropionylamino - 2 - aminobenzene -1 - sulfonic acid Chemical compound 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims description 2
- 229910006069 SO3H Inorganic materials 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 238000010186 staining Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- 238000004043 dyeing Methods 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 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 description 5
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000004744 fabric Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- CEQFOVLGLXCDCX-UHFFFAOYSA-N 2-[[4-(dimethylamino)phenyl]diazenyl]benzoic acid Chemical compound C1=CC(N(C)C)=CC=C1N=NC1=CC=CC=C1C(O)=O CEQFOVLGLXCDCX-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000009967 direct dyeing Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/465—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an acryloyl group, a quaternised or non-quaternised aminoalkyl carbonyl group or a (—N)n—CO—A—O—X or (—N)n—CO—A—Hal group, wherein A is an alkylene or alkylidene group, X is hydrogen or an acyl radical of an organic or inorganic acid, Hal is a halogen atom, and n is 0 or 1
- C09B62/47—Azo dyes
- C09B62/473—Monoazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH845567X | 1957-03-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1086366B true DE1086366B (de) | 1960-08-04 |
Family
ID=4541780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC16398A Pending DE1086366B (de) | 1957-03-08 | 1958-03-01 | Verfahren zur Herstellung von Monoazofarbstoffen |
Country Status (6)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1269265B (de) * | 1962-03-17 | 1968-05-30 | Basf Ag | Verfahren zur Herstellung wasserloeslicher reaktiver Azofarbstoffe |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3097039A (en) * | 1963-07-09 | Hoas oh | ||
| US3057673A (en) * | 1962-10-09 | Process for dyeing protein fibers with a | ||
| CH384747A (de) * | 1957-05-07 | 1965-02-26 | Ciba Geigy | Verfahren zur Herstellung neuer Farbstoffe |
| GB917873A (en) * | 1959-09-16 | 1963-02-06 | Ici Ltd | New dyestuffs containing halogenonitrobenzoylamino or halogenonitrobenzenesulphonylamino groups |
| US3170914A (en) * | 1961-12-28 | 1965-02-23 | Gen Aniline & Film Corp | Azo dyestuffs |
| US3248379A (en) * | 1962-11-21 | 1966-04-26 | Gen Aniline & Film Corp | Fiber reactive dyestuffs and process for their preparation |
| US3488343A (en) * | 1966-02-08 | 1970-01-06 | Ciba Ltd | Monoazo dyestuffs containing an acrylyl or benzoyl fiber-reactive substituent |
| US4036825A (en) * | 1971-11-05 | 1977-07-19 | Hoechst Aktiengesellschaft | Monoazo reactive dyestuffs |
| JPS57187358A (en) * | 1981-05-14 | 1982-11-18 | Sumitomo Chem Co Ltd | Production of arylazo-amino-naphtholsulfonic acid |
| JPS6033145B2 (ja) * | 1982-10-27 | 1985-08-01 | 三菱化学株式会社 | 記録液 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB545806A (en) * | 1940-11-11 | 1942-06-15 | Arthur Howard Knight | Manufacture of new monoazo acid dyestuffs |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1844031A (en) * | 1929-07-20 | 1932-02-09 | Gen Aniline Works Inc | Valuable acid wool azodyestuffs |
| US2102115A (en) * | 1933-08-22 | 1937-12-14 | Gen Aniline Works Inc | Monoazodyestuffs |
| US2183489A (en) * | 1937-06-09 | 1939-12-12 | Gen Aniline Works Inc | Monoazo dyestuffs |
| US2213697A (en) * | 1937-06-12 | 1940-09-03 | Gen Aniline & Film Corp | Monoazo dyestuffs |
| US2384754A (en) * | 1942-02-02 | 1945-09-11 | Ici Ltd | Monoazo dyestuffs |
| US2384755A (en) * | 1942-02-11 | 1945-09-11 | Ici Ltd | Monoazo dyestuffs |
-
0
- BE BE565484D patent/BE565484A/xx unknown
-
1957
- 1957-03-08 CH CH352429D patent/CH352429A/de unknown
- 1957-03-08 CH CH352425D patent/CH352425A/de unknown
-
1958
- 1958-02-14 FR FR1191570D patent/FR1191570A/fr not_active Expired
- 1958-02-18 GB GB5291/58A patent/GB845567A/en not_active Expired
- 1958-03-01 DE DEC16398A patent/DE1086366B/de active Pending
- 1958-03-03 US US718433A patent/US2973351A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB545806A (en) * | 1940-11-11 | 1942-06-15 | Arthur Howard Knight | Manufacture of new monoazo acid dyestuffs |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1269265B (de) * | 1962-03-17 | 1968-05-30 | Basf Ag | Verfahren zur Herstellung wasserloeslicher reaktiver Azofarbstoffe |
Also Published As
| Publication number | Publication date |
|---|---|
| CH352425A (de) | 1961-02-28 |
| BE565484A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| GB845567A (en) | 1960-08-24 |
| US2973351A (en) | 1961-02-28 |
| CH352429A (de) | 1961-02-28 |
| FR1191570A (fr) | 1959-10-20 |
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