CH618727A5 - Process for the preparation of new cationic dyes and product - Google Patents
Process for the preparation of new cationic dyes and product Download PDFInfo
- Publication number
- CH618727A5 CH618727A5 CH1190676A CH1190676A CH618727A5 CH 618727 A5 CH618727 A5 CH 618727A5 CH 1190676 A CH1190676 A CH 1190676A CH 1190676 A CH1190676 A CH 1190676A CH 618727 A5 CH618727 A5 CH 618727A5
- Authority
- CH
- Switzerland
- Prior art keywords
- alkyl
- formula
- dyes
- group
- indole
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims abstract description 23
- 125000002091 cationic group Chemical group 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title claims description 7
- 230000002378 acidificating effect Effects 0.000 claims abstract description 4
- 229920002994 synthetic fiber Polymers 0.000 claims abstract description 4
- 229940100198 alkylating agent Drugs 0.000 claims abstract 4
- 239000002168 alkylating agent Substances 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims abstract 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 28
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 claims description 16
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 14
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 14
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 10
- -1 acrylic nitrile Chemical class 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- CXLZQKDKJDQGBZ-UHFFFAOYSA-N 1h-indole;1h-pyrazole Chemical compound C=1C=NNC=1.C1=CC=C2NC=CC2=C1 CXLZQKDKJDQGBZ-UHFFFAOYSA-N 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 239000012209 synthetic fiber Substances 0.000 claims description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 150000008051 alkyl sulfates Chemical class 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000007858 starting material Substances 0.000 abstract 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 6
- 239000010930 yellow gold Substances 0.000 description 6
- 229910001097 yellow gold Inorganic materials 0.000 description 6
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 3
- XMOWAIVXKJWQBJ-UHFFFAOYSA-N 1-ethyl-2-methylindole Chemical compound C1=CC=C2N(CC)C(C)=CC2=C1 XMOWAIVXKJWQBJ-UHFFFAOYSA-N 0.000 description 2
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- SFWZZSXCWQTORH-UHFFFAOYSA-N 1-methyl-2-phenylindole Chemical compound C=1C2=CC=CC=C2N(C)C=1C1=CC=CC=C1 SFWZZSXCWQTORH-UHFFFAOYSA-N 0.000 description 1
- 229920002972 Acrylic fiber Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-O Pyrazolium Chemical compound C1=CN[NH+]=C1 WTKZEGDFNFYCGP-UHFFFAOYSA-O 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 150000004672 propanoic acids Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- C09B44/00—Azo dyes containing onium groups
- C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
- C09B44/14—1,2-Diazoles or hydrogenated 1,2-diazoles ; Pyrazolium; Indazolium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7529872A FR2326453A1 (fr) | 1975-09-30 | 1975-09-30 | Nouveaux colorants cationiques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH618727A5 true CH618727A5 (en) | 1980-08-15 |
Family
ID=9160631
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1190676A CH618727A5 (en) | 1975-09-30 | 1976-09-20 | Process for the preparation of new cationic dyes and product |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5242520A (enExample) |
| AR (1) | AR208150A1 (enExample) |
| BE (1) | BE846731A (enExample) |
| BR (1) | BR7606491A (enExample) |
| CH (1) | CH618727A5 (enExample) |
| DE (1) | DE2643639A1 (enExample) |
| FR (1) | FR2326453A1 (enExample) |
| GB (1) | GB1525768A (enExample) |
| NL (1) | NL7610715A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4315383A1 (de) * | 1993-05-08 | 1994-11-10 | Bayer Ag | Kationische Diazacyaninfarbstoffe |
| US6136080A (en) * | 1999-04-26 | 2000-10-24 | Eastman Kodak Company | Cationic azo dye for ink jet ink |
-
1975
- 1975-09-30 FR FR7529872A patent/FR2326453A1/fr active Granted
-
1976
- 1976-01-01 AR AR26484876A patent/AR208150A1/es active
- 1976-09-20 CH CH1190676A patent/CH618727A5/fr not_active IP Right Cessation
- 1976-09-28 JP JP11646776A patent/JPS5242520A/ja active Pending
- 1976-09-28 DE DE19762643639 patent/DE2643639A1/de active Pending
- 1976-09-28 NL NL7610715A patent/NL7610715A/xx not_active Application Discontinuation
- 1976-09-29 BE BE171067A patent/BE846731A/xx unknown
- 1976-09-29 BR BR7606491A patent/BR7606491A/pt unknown
- 1976-09-29 GB GB4034776A patent/GB1525768A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5242520A (en) | 1977-04-02 |
| FR2326453B1 (enExample) | 1979-04-06 |
| AR208150A1 (es) | 1976-11-30 |
| FR2326453A1 (fr) | 1977-04-29 |
| BR7606491A (pt) | 1977-07-05 |
| BE846731A (fr) | 1977-03-29 |
| GB1525768A (en) | 1978-09-20 |
| NL7610715A (nl) | 1977-04-01 |
| DE2643639A1 (de) | 1977-04-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |