DE1719066A1 - Wasserunloesliche Monoazofarbstoffe - Google Patents
Wasserunloesliche MonoazofarbstoffeInfo
- Publication number
- DE1719066A1 DE1719066A1 DE19681719066 DE1719066A DE1719066A1 DE 1719066 A1 DE1719066 A1 DE 1719066A1 DE 19681719066 DE19681719066 DE 19681719066 DE 1719066 A DE1719066 A DE 1719066A DE 1719066 A1 DE1719066 A1 DE 1719066A1
- Authority
- DE
- Germany
- Prior art keywords
- water
- general formula
- dyes
- insoluble monoazo
- monoazo dyes
- 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 48
- 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 7
- 229920000728 polyester Polymers 0.000 claims description 15
- 230000008878 coupling Effects 0.000 claims description 14
- 238000010168 coupling process Methods 0.000 claims description 14
- 238000005859 coupling reaction Methods 0.000 claims description 14
- -1 copper (I) compound Chemical class 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 238000004043 dyeing Methods 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical group C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 235000005811 Viola adunca Nutrition 0.000 description 8
- 240000009038 Viola odorata Species 0.000 description 8
- 235000013487 Viola odorata Nutrition 0.000 description 8
- 235000002254 Viola papilionacea Nutrition 0.000 description 8
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 244000172533 Viola sororia Species 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- 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 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 4
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- GPCCXIVDZANEJZ-UHFFFAOYSA-N 2-(n-ethylanilino)ethyl acetate Chemical compound CC(=O)OCCN(CC)C1=CC=CC=C1 GPCCXIVDZANEJZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- FPUKYOSOAAPHTN-UHFFFAOYSA-N n-[3-(diethylamino)phenyl]acetamide Chemical compound CCN(CC)C1=CC=CC(NC(C)=O)=C1 FPUKYOSOAAPHTN-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- XQGHEXBVXWBMGC-UHFFFAOYSA-N 2-[n-(2-acetyloxyethyl)anilino]ethyl acetate Chemical compound CC(=O)OCCN(CCOC(C)=O)C1=CC=CC=C1 XQGHEXBVXWBMGC-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009998 heat setting Methods 0.000 description 2
- 229940018564 m-phenylenediamine Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- REUFZACIJMPYOK-UHFFFAOYSA-N n-(2-phenylethyl)aniline Chemical compound C=1C=CC=CC=1NCCC1=CC=CC=C1 REUFZACIJMPYOK-UHFFFAOYSA-N 0.000 description 2
- CEJHSGIQMDDHDB-UHFFFAOYSA-N n-[2-(n-ethylanilino)ethyl]acetamide Chemical compound CC(=O)NCCN(CC)C1=CC=CC=C1 CEJHSGIQMDDHDB-UHFFFAOYSA-N 0.000 description 2
- CCGHPHXHRVGDHD-UHFFFAOYSA-N 2-(3-acetamido-n-ethylanilino)ethyl acetate Chemical compound CC(=O)OCCN(CC)C1=CC=CC(NC(C)=O)=C1 CCGHPHXHRVGDHD-UHFFFAOYSA-N 0.000 description 1
- VTZAZBMXVCDZIT-UHFFFAOYSA-N 2-(n-ethylanilino)ethyl 2-phenoxyacetate Chemical compound C=1C=CC=CC=1N(CC)CCOC(=O)COC1=CC=CC=C1 VTZAZBMXVCDZIT-UHFFFAOYSA-N 0.000 description 1
- RRGWFPOSTSQIQE-UHFFFAOYSA-N 2-[n-(2-cyanoethyl)anilino]ethyl acetate Chemical compound CC(=O)OCCN(CCC#N)C1=CC=CC=C1 RRGWFPOSTSQIQE-UHFFFAOYSA-N 0.000 description 1
- OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 description 1
- RFJPJHJLHHNWJS-UHFFFAOYSA-N 2-amino-3-methylsulfonyl-5-nitrobenzonitrile Chemical compound CS(=O)(=O)C1=CC([N+]([O-])=O)=CC(C#N)=C1N RFJPJHJLHHNWJS-UHFFFAOYSA-N 0.000 description 1
- GKEWEKFPHVSFEA-UHFFFAOYSA-N 2-amino-5-methylsulfonylbenzene-1,3-dicarbonitrile Chemical compound CS(=O)(=O)C1=CC(C#N)=C(N)C(C#N)=C1 GKEWEKFPHVSFEA-UHFFFAOYSA-N 0.000 description 1
- WYRNRZQRKCXPLA-UHFFFAOYSA-N 3-(n-ethylanilino)propanenitrile Chemical compound N#CCCN(CC)C1=CC=CC=C1 WYRNRZQRKCXPLA-UHFFFAOYSA-N 0.000 description 1
- YLNDNABNWASMFD-UHFFFAOYSA-N 4-[(1,3-dimethylimidazol-1-ium-2-yl)diazenyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1N=NC1=[N+](C)C=CN1C YLNDNABNWASMFD-UHFFFAOYSA-N 0.000 description 1
- MGYHJFGXQSZYOR-UHFFFAOYSA-N COC(=O)CCN(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound COC(=O)CCN(C1=CC=CC=C1)C1=CC=CC=C1 MGYHJFGXQSZYOR-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001448 anilines Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- OAXCYNSIHXILCT-UHFFFAOYSA-N n-[2-(diethylamino)phenyl]acetamide Chemical compound CCN(CC)C1=CC=CC=C1NC(C)=O OAXCYNSIHXILCT-UHFFFAOYSA-N 0.000 description 1
- 150000005002 naphthylamines Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/40—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms
- C09B43/42—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms by substituting radicals containing hetero atoms for —CN radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US791773*A US3627752A (en) | 1968-01-19 | 1969-01-16 | Water-insoluble monoazo dyestuffs |
| GB2869/69A GB1208405A (en) | 1968-01-19 | 1969-01-17 | Water-insoluble monoazo dyestuffs |
| GB2870/69A GB1208406A (en) | 1968-01-19 | 1969-01-17 | Water-insoluble monoazo dyestuffs |
| CH66369A CH508702A (de) | 1968-01-19 | 1969-01-17 | Verfahren zur Herstellung wasserunlöslicher Monoazofarbstoffe |
| FR6900733A FR2000434B1 (enrdf_load_stackoverflow) | 1968-01-19 | 1969-01-17 | |
| BE727048D BE727048A (enrdf_load_stackoverflow) | 1968-01-19 | 1969-01-17 | |
| US00196737A US3772267A (en) | 1968-01-19 | 1971-11-08 | 2-cyano-4-nitro-6-methylsulfonyl-1-(4'-diethylamino-2'-acetylamino-phenylazo)-benzene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC0044421 | 1968-01-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1719066A1 true DE1719066A1 (de) | 1971-02-18 |
Family
ID=7025791
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681719066 Pending DE1719066A1 (de) | 1968-01-19 | 1968-01-19 | Wasserunloesliche Monoazofarbstoffe |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1719066A1 (enrdf_load_stackoverflow) |
| NL (2) | NL6900441A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4046757A (en) * | 1968-10-18 | 1977-09-06 | Sandoz Ltd. | 2-Optionally substituted alkyl-and phenylsulfonylphenyl-azo-phenyl dyes and a process for their synthesis |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH560741A5 (enrdf_load_stackoverflow) * | 1970-02-05 | 1975-04-15 | Ciba Geigy Ag |
-
1968
- 1968-01-19 DE DE19681719066 patent/DE1719066A1/de active Pending
-
1969
- 1969-01-10 NL NL6900441A patent/NL6900441A/xx unknown
- 1969-01-10 NL NL6900442A patent/NL6900442A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4046757A (en) * | 1968-10-18 | 1977-09-06 | Sandoz Ltd. | 2-Optionally substituted alkyl-and phenylsulfonylphenyl-azo-phenyl dyes and a process for their synthesis |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6900441A (enrdf_load_stackoverflow) | 1969-07-22 |
| NL6900442A (enrdf_load_stackoverflow) | 1969-07-22 |
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