DE2120877C3 - In Wasser schwer lösliche Monoazoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung - Google Patents
In Wasser schwer lösliche Monoazoverbindungen, Verfahren zu ihrer Herstellung und ihre VerwendungInfo
- Publication number
- DE2120877C3 DE2120877C3 DE19712120877 DE2120877A DE2120877C3 DE 2120877 C3 DE2120877 C3 DE 2120877C3 DE 19712120877 DE19712120877 DE 19712120877 DE 2120877 A DE2120877 A DE 2120877A DE 2120877 C3 DE2120877 C3 DE 2120877C3
- Authority
- DE
- Germany
- Prior art keywords
- coo
- water
- pink
- parts
- blue
- 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
- 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 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title description 8
- 238000000034 method Methods 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 6
- 239000000975 dye Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000004043 dyeing Methods 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 230000002209 hydrophobic effect Effects 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000000986 disperse dye Substances 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 230000008022 sublimation Effects 0.000 claims 1
- 238000000859 sublimation Methods 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- 239000000460 chlorine Substances 0.000 description 31
- -1 cyano, nitro, methylsulfo- Chemical class 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- MUHLVSZIVTURCZ-UHFFFAOYSA-N 2-amino-3-bromo-5-nitrobenzonitrile Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1C#N MUHLVSZIVTURCZ-UHFFFAOYSA-N 0.000 description 1
- SGHZXLIDFTYFHQ-UHFFFAOYSA-L Brilliant Blue Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SGHZXLIDFTYFHQ-UHFFFAOYSA-L 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 239000004952 Polyamide Substances 0.000 description 1
- 241001115903 Raphus cucullatus Species 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
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 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
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229940080236 sodium cetyl sulfate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 238000005406 washing Methods 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
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
-
- 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
- C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
-
- 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
- C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
- C09B43/20—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with monocarboxylic acids, carbamic acid esters or halides, mono- isocyanates or haloformic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH680870A CH526615A (de) | 1970-05-06 | 1970-05-06 | Verfahren zur Herstellung in Wasser schwer löslicher Azoverbindungen |
| CH1924970 | 1970-12-29 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2120877A1 DE2120877A1 (de) | 1971-11-25 |
| DE2120877B2 DE2120877B2 (de) | 1979-07-19 |
| DE2120877C3 true DE2120877C3 (de) | 1980-03-20 |
Family
ID=25700211
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712120876 Pending DE2120876A1 (de) | 1970-05-06 | 1971-04-28 | In Wasser schwer lösliche Azoverbindungen, ihre Herstellung und Verwendung |
| DE19712120877 Expired DE2120877C3 (de) | 1970-05-06 | 1971-04-28 | In Wasser schwer lösliche Monoazoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712120876 Pending DE2120876A1 (de) | 1970-05-06 | 1971-04-28 | In Wasser schwer lösliche Azoverbindungen, ihre Herstellung und Verwendung |
Country Status (13)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4042580A (en) * | 1970-05-06 | 1977-08-16 | Sandoz Ltd. | Phenylazophenyl dyes having an alkoxyacylamino group on the coupling component radical |
| US4038269A (en) * | 1970-05-06 | 1977-07-26 | Sandoz Ltd. | 2'-alkoxyacylamino-4'-alkylamino-4-nitro-1,1'-azobenzene disperse dyes |
| US4667023A (en) * | 1973-07-16 | 1987-05-19 | Sandoz Ltd. | 4-(2'-halo-4'-nitrophenylazo)-2-2[2'-(C1-2 alkoxy or 2"-methoxyethoxy)ethoxycarbonylamino --N,N-di-C2-3 alkylanilines |
| GB1565531A (en) * | 1976-02-05 | 1980-04-23 | Ici Ltd | Diperse monoazo dyestuffs |
| US4076706A (en) * | 1976-11-15 | 1978-02-28 | Eastman Kodak Company | Disperse dyes from 2-cyano-4,6-dinitroaniline and selected 2(2'-alkoxy-5'-acylamidoanilino)alkanes |
| CH633307A5 (de) * | 1977-03-16 | 1982-11-30 | Ciba Geigy Ag | Azofarbstoffe. |
| LU76960A1 (enrdf_load_stackoverflow) * | 1977-03-16 | 1978-10-18 | ||
| LU78553A1 (de) * | 1977-11-21 | 1979-06-13 | Ciba Geigy Ag | Monoazofarbstoffe,verfahren zu deren herstellung und ihre verwendung |
| IT1122520B (it) * | 1978-09-08 | 1986-04-23 | Ici Ltd | Coloranti |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1167704A (fr) * | 1955-07-13 | 1958-11-28 | Sandoz Ag | Colorants mono-azoïques insolubles dans l'eau, leur procédé de préparation et leurs applications |
| CH343560A (de) * | 1956-07-21 | 1959-12-31 | Sandoz Ag | Verfahren zur Herstellung wasserunlöslicher Monoazofarbstoffe |
| FR1383356A (fr) * | 1963-02-21 | 1964-12-24 | Ciba Geigy | Colorants monoazoïques insolubles dans l'eau et leur procédé d'obtention |
| FR1361809A (fr) * | 1963-07-08 | 1964-05-22 | Bayer Ag | Colorants monoazoïques et leur procédé de fabrication |
| FR1377496A (fr) * | 1963-09-24 | 1964-11-06 | Ici Ltd | Nouveaux colorants dispersés |
| CH465735A (de) * | 1964-03-13 | 1968-11-30 | Sandoz Ag | Verfahren zur Herstellung von Monoazofarbstoffen |
| FR1486349A (fr) * | 1965-07-12 | 1967-06-23 | Sandoz Sa | Colorants azoïques, leur procédé de fabrication et leurs applications |
-
1971
- 1971-04-27 CY CY88271A patent/CY882A/xx unknown
- 1971-04-27 GB GB1167671A patent/GB1352059A/en not_active Expired
- 1971-04-27 GB GB1170871A patent/GB1349003A/en not_active Expired
- 1971-04-28 DE DE19712120876 patent/DE2120876A1/de active Pending
- 1971-04-28 DE DE19712120877 patent/DE2120877C3/de not_active Expired
- 1971-05-04 ES ES390851A patent/ES390851A1/es not_active Expired
- 1971-05-04 ES ES390852A patent/ES390852A1/es not_active Expired
- 1971-05-05 BE BE766772A patent/BE766772A/xx unknown
- 1971-05-05 BE BE766773A patent/BE766773A/xx unknown
- 1971-05-05 CA CA112200A patent/CA925856A/en not_active Expired
- 1971-05-05 NL NL7106130A patent/NL7106130A/xx unknown
- 1971-05-05 DD DD15488071A patent/DD95069A5/xx unknown
- 1971-05-05 NL NL7106129A patent/NL7106129A/xx unknown
- 1971-05-05 FR FR7116174A patent/FR2088375B1/fr not_active Expired
- 1971-05-05 FR FR7116173A patent/FR2088374B1/fr not_active Expired
- 1971-05-05 CA CA112201A patent/CA925857A/en not_active Expired
- 1971-05-06 JP JP3010271A patent/JPS5426575B1/ja active Pending
-
1976
- 1976-11-30 KE KE268176A patent/KE2681A/xx unknown
- 1976-12-16 HK HK79876A patent/HK79876A/xx unknown
-
1977
- 1977-12-30 MY MY7700100A patent/MY7700100A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2088374A1 (enrdf_load_stackoverflow) | 1972-01-07 |
| DD95069A5 (enrdf_load_stackoverflow) | 1973-01-12 |
| ES390852A1 (es) | 1974-08-01 |
| FR2088375B1 (enrdf_load_stackoverflow) | 1975-07-04 |
| HK79876A (en) | 1976-12-24 |
| DE2120877A1 (de) | 1971-11-25 |
| NL7106129A (enrdf_load_stackoverflow) | 1971-11-09 |
| KE2681A (en) | 1976-12-24 |
| GB1349003A (en) | 1974-03-27 |
| GB1352059A (en) | 1974-05-15 |
| DE2120876A1 (de) | 1971-11-25 |
| NL7106130A (enrdf_load_stackoverflow) | 1971-11-09 |
| FR2088375A1 (enrdf_load_stackoverflow) | 1972-01-07 |
| CA925856A (en) | 1973-05-08 |
| MY7700100A (en) | 1977-12-31 |
| CY882A (en) | 1977-03-18 |
| BE766773A (fr) | 1971-10-01 |
| JPS5426575B1 (enrdf_load_stackoverflow) | 1979-09-05 |
| BE766772A (fr) | 1971-10-01 |
| ES390851A1 (es) | 1974-08-01 |
| FR2088374B1 (enrdf_load_stackoverflow) | 1975-08-22 |
| DE2120877B2 (de) | 1979-07-19 |
| CA925857A (en) | 1973-05-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |