DE2419050B2 - Monoazofarbstoffe, verfahren zu deren herstellung und ihre verwendung - Google Patents
Monoazofarbstoffe, verfahren zu deren herstellung und ihre verwendungInfo
- Publication number
- DE2419050B2 DE2419050B2 DE19742419050 DE2419050A DE2419050B2 DE 2419050 B2 DE2419050 B2 DE 2419050B2 DE 19742419050 DE19742419050 DE 19742419050 DE 2419050 A DE2419050 A DE 2419050A DE 2419050 B2 DE2419050 B2 DE 2419050B2
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- butyl
- monoazo dyes
- dyes
- manufacturing
- 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.)
- Granted
Links
- 239000000975 dye Substances 0.000 title claims description 22
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical compound [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
- 239000000460 chlorine Substances 0.000 description 12
- 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 9
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 206010039587 Scarlet Fever Diseases 0.000 description 4
- 229910052770 Uranium Inorganic materials 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
- 239000002657 fibrous material Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 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
- 150000002431 hydrogen Chemical class 0.000 description 2
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 2
- -1 n-hexyl n-pentyl Chemical group 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- WETJSRQUPWCLFW-UHFFFAOYSA-N 2-amino-5-chlorobenzene-1,3-dicarbonitrile Chemical compound NC1=C(C#N)C=C(Cl)C=C1C#N WETJSRQUPWCLFW-UHFFFAOYSA-N 0.000 description 1
- OREVCMGFYSUYPX-UHFFFAOYSA-N 4-amino-3-chlorobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1Cl OREVCMGFYSUYPX-UHFFFAOYSA-N 0.000 description 1
- RRCAJFYQXKPXOJ-UHFFFAOYSA-N 4-aminobenzene-1,2-dicarbonitrile Chemical compound NC1=CC=C(C#N)C(C#N)=C1 RRCAJFYQXKPXOJ-UHFFFAOYSA-N 0.000 description 1
- IPMNLGOBXWTQRV-UHFFFAOYSA-N 4-aminobenzene-1,3-dicarbonitrile Chemical compound NC1=CC=C(C#N)C=C1C#N IPMNLGOBXWTQRV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000001714 carbamic acid halides Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000002270 dispersing agent Substances 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000007858 starting material Substances 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
- 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)
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742419050 DE2419050B2 (de) | 1974-04-20 | 1974-04-20 | Monoazofarbstoffe, verfahren zu deren herstellung und ihre verwendung |
| GB1522775A GB1452469A (en) | 1974-04-20 | 1975-04-14 | Azo dyestuffs containing n-alkylaminocarbonyl-oxyalkyl-n- cyanoalkyl-amino groups |
| NL7504584A NL7504584A (nl) | 1974-04-20 | 1975-04-17 | Azokleurstoffen. |
| CH502375A CH585777A5 (enExample) | 1974-04-20 | 1975-04-18 | |
| IT2251275A IT1037438B (it) | 1974-04-20 | 1975-04-18 | Coloranti azoici |
| JP4662975A JPS50145426A (enExample) | 1974-04-20 | 1975-04-18 | |
| BE155520A BE828085A (fr) | 1974-04-20 | 1975-04-18 | Colorants azoiques, leur obtention et leurs applications |
| FR7512151A FR2268055B1 (enExample) | 1974-04-20 | 1975-04-18 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742419050 DE2419050B2 (de) | 1974-04-20 | 1974-04-20 | Monoazofarbstoffe, verfahren zu deren herstellung und ihre verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2419050A1 DE2419050A1 (de) | 1975-10-30 |
| DE2419050B2 true DE2419050B2 (de) | 1976-09-02 |
Family
ID=5913399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742419050 Granted DE2419050B2 (de) | 1974-04-20 | 1974-04-20 | Monoazofarbstoffe, verfahren zu deren herstellung und ihre verwendung |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS50145426A (enExample) |
| BE (1) | BE828085A (enExample) |
| CH (1) | CH585777A5 (enExample) |
| DE (1) | DE2419050B2 (enExample) |
| FR (1) | FR2268055B1 (enExample) |
| GB (1) | GB1452469A (enExample) |
| IT (1) | IT1037438B (enExample) |
| NL (1) | NL7504584A (enExample) |
-
1974
- 1974-04-20 DE DE19742419050 patent/DE2419050B2/de active Granted
-
1975
- 1975-04-14 GB GB1522775A patent/GB1452469A/en not_active Expired
- 1975-04-17 NL NL7504584A patent/NL7504584A/xx unknown
- 1975-04-18 JP JP4662975A patent/JPS50145426A/ja active Pending
- 1975-04-18 IT IT2251275A patent/IT1037438B/it active
- 1975-04-18 FR FR7512151A patent/FR2268055B1/fr not_active Expired
- 1975-04-18 CH CH502375A patent/CH585777A5/xx not_active IP Right Cessation
- 1975-04-18 BE BE155520A patent/BE828085A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2268055A1 (enExample) | 1975-11-14 |
| IT1037438B (it) | 1979-11-10 |
| NL7504584A (nl) | 1975-10-22 |
| BE828085A (fr) | 1975-10-20 |
| CH585777A5 (enExample) | 1977-03-15 |
| FR2268055B1 (enExample) | 1978-12-29 |
| GB1452469A (en) | 1976-10-13 |
| JPS50145426A (enExample) | 1975-11-21 |
| DE2419050A1 (de) | 1975-10-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |