DE2738885C2 - - Google Patents
Info
- Publication number
- DE2738885C2 DE2738885C2 DE2738885A DE2738885A DE2738885C2 DE 2738885 C2 DE2738885 C2 DE 2738885C2 DE 2738885 A DE2738885 A DE 2738885A DE 2738885 A DE2738885 A DE 2738885A DE 2738885 C2 DE2738885 C2 DE 2738885C2
- Authority
- DE
- Germany
- Prior art keywords
- amino
- dyes
- nitro
- formula
- phenyl
- 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
- -1 C1- to C4-alkoxy Chemical group 0.000 claims description 14
- 239000000975 dye Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000987 azo dye Substances 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000001989 diazonium salts Chemical class 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 2
- 239000004615 ingredient Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000004753 textile Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- CFBYBPOBHYGXNZ-UHFFFAOYSA-N 2-amino-4-methyl-5-nitrothiophene-3-carbonitrile Chemical compound CC1=C([N+]([O-])=O)SC(N)=C1C#N CFBYBPOBHYGXNZ-UHFFFAOYSA-N 0.000 description 1
- RMSVWOYCWFNSCM-UHFFFAOYSA-N 2-amino-4-phenylthiophene-3-carbonitrile Chemical compound N#CC1=C(N)SC=C1C1=CC=CC=C1 RMSVWOYCWFNSCM-UHFFFAOYSA-N 0.000 description 1
- CFKZMYPOJOKAAD-UHFFFAOYSA-N 2-amino-5-nitrothiophene-3-carbonitrile Chemical compound NC=1SC([N+]([O-])=O)=CC=1C#N CFKZMYPOJOKAAD-UHFFFAOYSA-N 0.000 description 1
- XVGHZFWFGXDIOU-UHFFFAOYSA-N 2-aminothiophene-3-carbonitrile Chemical compound NC=1SC=CC=1C#N XVGHZFWFGXDIOU-UHFFFAOYSA-N 0.000 description 1
- DZRZHFOFVWAKGT-UHFFFAOYSA-N 3,5-dinitrothiophen-2-amine Chemical compound NC=1SC([N+]([O-])=O)=CC=1[N+]([O-])=O DZRZHFOFVWAKGT-UHFFFAOYSA-N 0.000 description 1
- KDILIMALWBUMCY-UHFFFAOYSA-N 4-methyl-3,5-dinitrothiophen-2-amine Chemical compound CC1=C([N+]([O-])=O)SC(N)=C1[N+]([O-])=O KDILIMALWBUMCY-UHFFFAOYSA-N 0.000 description 1
- TXUDBQMERILDNB-UHFFFAOYSA-N 7-nitro-1,2-benzothiazol-4-amine Chemical compound NC1=CC=C([N+]([O-])=O)C2=C1C=NS2 TXUDBQMERILDNB-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- MKJQYFVTEPGXIE-UHFFFAOYSA-N ethyl 2-aminothiophene-3-carboxylate Chemical compound CCOC(=O)C=1C=CSC=1N MKJQYFVTEPGXIE-UHFFFAOYSA-N 0.000 description 1
- NCCMCRFYSZRBBG-UHFFFAOYSA-N ethyl 5-amino-4-cyano-3-methylthiophene-2-carboxylate Chemical compound CCOC(=O)C=1SC(N)=C(C#N)C=1C NCCMCRFYSZRBBG-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- OVLUSSXPOANNKZ-UHFFFAOYSA-N methyl 2-amino-5-nitrothiophene-3-carboxylate Chemical compound COC(=O)C=1C=C([N+]([O-])=O)SC=1N OVLUSSXPOANNKZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FAXWKQAPUYLLPC-UHFFFAOYSA-N n,4-diphenyl-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1NC(SC=1)=NC=1C1=CC=CC=C1 FAXWKQAPUYLLPC-UHFFFAOYSA-N 0.000 description 1
- OAOUJXZFLXNQFK-UHFFFAOYSA-N n,n-dimethyl-4-phenyl-1,3-thiazol-2-amine Chemical compound S1C(N(C)C)=NC(C=2C=CC=CC=2)=C1 OAOUJXZFLXNQFK-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/12—Disazo dyes from other coupling components "C"
- C09B31/14—Heterocyclic components
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3691—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing nitrogen and sulfur as heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772738885 DE2738885A1 (de) | 1977-08-29 | 1977-08-29 | Azofarbstoffe |
| IT26691/78A IT1097943B (it) | 1977-08-29 | 1978-08-10 | Azocoloranti |
| FR7823988A FR2401960A1 (fr) | 1977-08-29 | 1978-08-17 | Colorants azoiques |
| CH893978A CH634864A5 (de) | 1977-08-29 | 1978-08-23 | Azofarbstoffe. |
| GB7834704A GB2004561B (en) | 1977-08-29 | 1978-08-25 | Azo dyes |
| JP10449878A JPS5446226A (en) | 1977-08-29 | 1978-08-29 | Novel azo dyestuff |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772738885 DE2738885A1 (de) | 1977-08-29 | 1977-08-29 | Azofarbstoffe |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2738885A1 DE2738885A1 (de) | 1979-03-22 |
| DE2738885C2 true DE2738885C2 (US06521211-20030218-C00004.png) | 1988-07-21 |
Family
ID=6017579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772738885 Granted DE2738885A1 (de) | 1977-08-29 | 1977-08-29 | Azofarbstoffe |
Country Status (6)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2816507A1 (de) * | 1978-04-15 | 1979-10-25 | Basf Ag | Saure azofarbstoffe mit thiazolkupplungskomponenten |
| DE2910806A1 (de) * | 1979-03-20 | 1980-10-02 | Basf Ag | Farbstoffe der thiazolreihe |
| DE3427201A1 (de) * | 1984-07-24 | 1986-01-30 | Basf Ag, 6700 Ludwigshafen | Heterocyclische azofarbstoffe |
| GB8704727D0 (en) * | 1987-02-27 | 1987-08-05 | Ici Plc | Aromatic disazo compound |
| JPS63315602A (ja) * | 1987-06-12 | 1988-12-23 | 美津濃株式会社 | パツド |
| US5132412A (en) * | 1988-10-01 | 1992-07-21 | Basf Aktiengesellschaft | Thiazoleazo dyes having a diazo component from the isothiazole or thiadiazole series |
| DE3833442A1 (de) * | 1988-10-01 | 1990-04-12 | Basf Ag | Thiophenazofarbstoffe mit einer kupplungskomponente aus der thiazolreihe |
| US5216139A (en) * | 1988-10-01 | 1993-06-01 | Basf Aktiengesellschaft | Thiopheneazo dye based on a coupling component of the thiazole series |
| DE3910289A1 (de) * | 1989-03-30 | 1990-10-04 | Basf Ag | Azofarbstoffe mit einer diazokomponente aus der aminobenzisothiazolreihe |
| DE3910408A1 (de) * | 1989-03-31 | 1990-10-04 | Basf Ag | Azofarbstoffe, deren diazo- und kupplungskomponente aus der thiazolreihe stammt |
| DE3917455A1 (de) * | 1989-05-30 | 1990-12-06 | Basf Ag | Benzisothiazolazofarbstoffe mit einer kupplungskomponente aus der thiazol- oder pyridinreihe |
| JP2008248211A (ja) * | 2007-03-30 | 2008-10-16 | Fujifilm Corp | アゾ色素およびアゾ化合物 |
| JP2008248212A (ja) * | 2007-03-30 | 2008-10-16 | Fujifilm Corp | アゾ色素およびアゾ化合物 |
| US10272457B2 (en) | 2015-12-09 | 2019-04-30 | Joseph A. McDonnell | Dual sprayer, and dual sprayer with dual chamber bottle |
| US10926276B2 (en) | 2015-12-09 | 2021-02-23 | Joseph A. McDonnell | Dual sprayer and foam sprayer attachment |
| USD821541S1 (en) | 2015-12-30 | 2018-06-26 | Joseph A. McDonnell | Dual sprayer |
| USD944924S1 (en) | 2018-05-08 | 2022-03-01 | For Life Products, Llc | Dual sprayer with screw connection and foam sprayer attachment |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3770719A (en) * | 1967-12-07 | 1973-11-06 | Eastman Kodak Co | 2-amino-4-(azoyl)-azo-thiazole compounds and quaternary derivative thereof |
| US3816391A (en) * | 1971-12-01 | 1974-06-11 | Eastman Kodak Co | 2-amino-4-aryl-5-(2-cyano-4,6-dinitro-phenylazo)thiazole compounds |
-
1977
- 1977-08-29 DE DE19772738885 patent/DE2738885A1/de active Granted
-
1978
- 1978-08-10 IT IT26691/78A patent/IT1097943B/it active
- 1978-08-17 FR FR7823988A patent/FR2401960A1/fr active Granted
- 1978-08-23 CH CH893978A patent/CH634864A5/de not_active IP Right Cessation
- 1978-08-25 GB GB7834704A patent/GB2004561B/en not_active Expired
- 1978-08-29 JP JP10449878A patent/JPS5446226A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT1097943B (it) | 1985-08-31 |
| CH634864A5 (de) | 1983-02-28 |
| JPS5446226A (en) | 1979-04-12 |
| JPS6228818B2 (US06521211-20030218-C00004.png) | 1987-06-23 |
| DE2738885A1 (de) | 1979-03-22 |
| GB2004561B (en) | 1982-04-21 |
| FR2401960B3 (US06521211-20030218-C00004.png) | 1981-03-27 |
| GB2004561A (en) | 1979-04-04 |
| IT7826691A0 (it) | 1978-08-10 |
| FR2401960A1 (fr) | 1979-03-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8330 | Complete renunciation |