DE2520076C3 - Monoazofarbstoffe sowie deren Herstellung und Verwendung - Google Patents
Monoazofarbstoffe sowie deren Herstellung und VerwendungInfo
- Publication number
- DE2520076C3 DE2520076C3 DE19752520076 DE2520076A DE2520076C3 DE 2520076 C3 DE2520076 C3 DE 2520076C3 DE 19752520076 DE19752520076 DE 19752520076 DE 2520076 A DE2520076 A DE 2520076A DE 2520076 C3 DE2520076 C3 DE 2520076C3
- Authority
- DE
- Germany
- Prior art keywords
- formula
- dyes
- monoazo dyes
- hydrogen
- production
- 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
- 239000000975 dye Substances 0.000 title claims description 17
- 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 6
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000000460 chlorine Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 9
- 230000008878 coupling Effects 0.000 description 9
- 238000010168 coupling process Methods 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- 238000004043 dyeing Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 239000000835 fiber Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 4
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000987 azo dye Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- VRVUKQWNRPNACD-UHFFFAOYSA-N 1-isocyanatopentane Chemical compound CCCCCN=C=O VRVUKQWNRPNACD-UHFFFAOYSA-N 0.000 description 1
- CGPPWNTVTNCHDO-UHFFFAOYSA-N 2-bromo-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Br CGPPWNTVTNCHDO-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- -1 amide fluoride halides Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- ANJPRQPHZGHVQB-UHFFFAOYSA-N hexyl isocyanate Chemical compound CCCCCCN=C=O ANJPRQPHZGHVQB-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- CPAQPZOGPWRXIF-UHFFFAOYSA-N n-hexylcarbamoyl chloride Chemical compound CCCCCCNC(Cl)=O CPAQPZOGPWRXIF-UHFFFAOYSA-N 0.000 description 1
- LESQCMHWQMVETO-UHFFFAOYSA-N n-pentylcarbamoyl chloride Chemical compound CCCCCNC(Cl)=O LESQCMHWQMVETO-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
- 238000002360 preparation method Methods 0.000 description 1
- STZCRXQWRGQSJD-UHFFFAOYSA-N sodium;4-[[4-(dimethylamino)phenyl]diazenyl]benzenesulfonic acid Chemical compound [Na+].C1=CC(N(C)C)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 STZCRXQWRGQSJD-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
-
- 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0823—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by CN
- C09B29/0826—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by CN having N(-alkenylene/-alkynylene-O)(-alkenylene/-alkynylene-CN)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752520076 DE2520076C3 (de) | 1975-05-06 | 1975-05-06 | Monoazofarbstoffe sowie deren Herstellung und Verwendung |
| ES447337A ES447337A1 (es) | 1975-05-06 | 1976-04-24 | Procedimiento para la obtencion de colorantes azoicos. |
| JP4866376A JPS51134724A (en) | 1975-05-06 | 1976-04-30 | Azo dyes |
| CH553476A CH617955A5 (en) | 1975-05-06 | 1976-05-03 | Process for preparing azo dyes |
| GB1817276A GB1494165A (en) | 1975-05-06 | 1976-05-04 | Azo dyestuffs |
| FR7613409A FR2310384A1 (fr) | 1975-05-06 | 1976-05-05 | Colorants azoiques, leur obtention et leur application |
| BR7602822A BR7602822A (pt) | 1975-05-06 | 1976-05-05 | Processo para a preparacao de corantes azoicos e sua aplicacao |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752520076 DE2520076C3 (de) | 1975-05-06 | 1975-05-06 | Monoazofarbstoffe sowie deren Herstellung und Verwendung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2520076A1 DE2520076A1 (de) | 1976-11-18 |
| DE2520076B2 DE2520076B2 (de) | 1979-04-12 |
| DE2520076C3 true DE2520076C3 (de) | 1979-11-29 |
Family
ID=5945860
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752520076 Expired DE2520076C3 (de) | 1975-05-06 | 1975-05-06 | Monoazofarbstoffe sowie deren Herstellung und Verwendung |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS51134724A (enExample) |
| BR (1) | BR7602822A (enExample) |
| CH (1) | CH617955A5 (enExample) |
| DE (1) | DE2520076C3 (enExample) |
| ES (1) | ES447337A1 (enExample) |
| FR (1) | FR2310384A1 (enExample) |
| GB (1) | GB1494165A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58169216U (ja) * | 1982-05-07 | 1983-11-11 | 日本精工株式会社 | ストツパ−つき動圧軸受スピンドル |
-
1975
- 1975-05-06 DE DE19752520076 patent/DE2520076C3/de not_active Expired
-
1976
- 1976-04-24 ES ES447337A patent/ES447337A1/es not_active Expired
- 1976-04-30 JP JP4866376A patent/JPS51134724A/ja active Granted
- 1976-05-03 CH CH553476A patent/CH617955A5/de not_active IP Right Cessation
- 1976-05-04 GB GB1817276A patent/GB1494165A/en not_active Expired
- 1976-05-05 FR FR7613409A patent/FR2310384A1/fr active Granted
- 1976-05-05 BR BR7602822A patent/BR7602822A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51134724A (en) | 1976-11-22 |
| BR7602822A (pt) | 1976-11-09 |
| DE2520076A1 (de) | 1976-11-18 |
| DE2520076B2 (de) | 1979-04-12 |
| GB1494165A (en) | 1977-12-07 |
| FR2310384A1 (fr) | 1976-12-03 |
| CH617955A5 (en) | 1980-06-30 |
| ES447337A1 (es) | 1977-06-16 |
| FR2310384B1 (enExample) | 1980-05-30 |
| JPS5711337B2 (enExample) | 1982-03-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |