DE2134518C3 - Verfahren zur Herstellung von Verbindungen der Benzothloxanthenreihe - Google Patents
Verfahren zur Herstellung von Verbindungen der BenzothloxanthenreiheInfo
- Publication number
- DE2134518C3 DE2134518C3 DE2134518A DE2134518A DE2134518C3 DE 2134518 C3 DE2134518 C3 DE 2134518C3 DE 2134518 A DE2134518 A DE 2134518A DE 2134518 A DE2134518 A DE 2134518A DE 2134518 C3 DE2134518 C3 DE 2134518C3
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- series
- copper
- weight
- parts
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000001879 copper Chemical class 0.000 claims description 7
- 150000001989 diazonium salts Chemical class 0.000 claims description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- YEBQUUKDSJCPIX-UHFFFAOYSA-N 12h-benzo[a]thioxanthene Chemical class C1=CC=CC2=C3CC4=CC=CC=C4SC3=CC=C21 YEBQUUKDSJCPIX-UHFFFAOYSA-N 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 2
- -1 nitrosyl groups Chemical group 0.000 claims description 2
- VSFIHNGNLNCFRO-UHFFFAOYSA-N 8-phenylsulfanylnaphthalen-1-amine Chemical class C=12C(N)=CC=CC2=CC=CC=1SC1=CC=CC=C1 VSFIHNGNLNCFRO-UHFFFAOYSA-N 0.000 claims 1
- ROELONHFRCNJMQ-UHFFFAOYSA-N NC1(C=CC=CC1)SC1=CC=CC2=CC=CC=C12 Chemical class NC1(C=CC=CC1)SC1=CC=CC2=CC=CC=C12 ROELONHFRCNJMQ-UHFFFAOYSA-N 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 12
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000006193 diazotization reaction Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 238000002835 absorbance Methods 0.000 description 4
- 230000008033 biological extinction Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- AFWWTAZRZLTZSH-UHFFFAOYSA-N 3-(2-aminophenyl)sulfanylbenzo[b]phenalen-7-one Chemical compound NC1=CC=CC=C1SC1=CC=C2C3=C1C=CC=C3C(=O)C1=CC=CC=C12 AFWWTAZRZLTZSH-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- MYYDJHOZTVOGKJ-UHFFFAOYSA-N [4-(2-aminophenyl)sulfanylnaphthalene-1-carbonyl] 4-(2-aminophenyl)sulfanylnaphthalene-1-carboxylate Chemical compound NC1=CC=CC=C1SC(C1=CC=CC=C11)=CC=C1C(=O)OC(=O)C(C1=CC=CC=C11)=CC=C1SC1=CC=CC=C1N MYYDJHOZTVOGKJ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000005749 Copper compound Substances 0.000 description 1
- 239000004157 Nitrosyl chloride Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
- 235000019392 nitrosyl chloride Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000002351 wastewater 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/14—Benzoxanthene dyes; Benzothioxanthene dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2134518A DE2134518C3 (de) | 1971-07-10 | 1971-07-10 | Verfahren zur Herstellung von Verbindungen der Benzothloxanthenreihe |
| CH1015372A CH574437A5 (OSRAM) | 1971-07-10 | 1972-07-06 | |
| JP6763672A JPS558545B1 (OSRAM) | 1971-07-10 | 1972-07-07 | |
| AU44332/72A AU461200B2 (en) | 1971-07-10 | 1972-07-07 | Process for preparing compounds ofthe benothiozanthene series |
| GB3194372A GB1393956A (en) | 1971-07-10 | 1972-07-07 | Process for the preparation of compounds containing the benzothioxanthene nucleus |
| IT2680172A IT962666B (it) | 1971-07-10 | 1972-07-08 | Tubo a raggi catodici dotato di una maschera forata processo per la preparazione di com posti della serie del benzotioxan tene |
| IT26803/72A IT962668B (it) | 1971-07-10 | 1972-07-08 | Processo per la preparazione di composti della serie del benzotioxantene |
| FR7224904A FR2145992A5 (OSRAM) | 1971-07-10 | 1972-07-10 | |
| US00270257A US3829439A (en) | 1971-07-10 | 1972-07-10 | Process for preparing compounds of the benzothioxanthene series |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2134518A DE2134518C3 (de) | 1971-07-10 | 1971-07-10 | Verfahren zur Herstellung von Verbindungen der Benzothloxanthenreihe |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2134518A1 DE2134518A1 (de) | 1973-01-25 |
| DE2134518B2 DE2134518B2 (de) | 1978-11-16 |
| DE2134518C3 true DE2134518C3 (de) | 1979-08-16 |
Family
ID=5813282
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2134518A Expired DE2134518C3 (de) | 1971-07-10 | 1971-07-10 | Verfahren zur Herstellung von Verbindungen der Benzothloxanthenreihe |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3829439A (OSRAM) |
| JP (1) | JPS558545B1 (OSRAM) |
| AU (1) | AU461200B2 (OSRAM) |
| CH (1) | CH574437A5 (OSRAM) |
| DE (1) | DE2134518C3 (OSRAM) |
| FR (1) | FR2145992A5 (OSRAM) |
| GB (1) | GB1393956A (OSRAM) |
| IT (1) | IT962668B (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4041853A1 (de) * | 1990-12-24 | 1992-06-25 | Cassella Ag | Verfahren zur herstellung von benzothioxanthen-farbstoffen |
| DE4202911A1 (de) * | 1992-02-01 | 1993-08-05 | Cassella Ag | Farbstoffmischungen zum faerben von textilen hydrophoben fasermaterialien |
| US6713636B2 (en) | 2001-08-20 | 2004-03-30 | 3M Innovative Properties Company | Thloxanthone dyes with improved solubility and a method of preparing 2-oxybenzanthrones as intermediate materials for making of these dyes |
| US6531613B1 (en) | 2001-08-20 | 2003-03-11 | 3M Innovative Properties Company | Thioxanthone dyes with improved solubility |
| US6841236B2 (en) | 2001-08-20 | 2005-01-11 | 3M Innovative Properties Co. | Articles containing thioxanthone dyes |
| EP2085431B1 (en) * | 2008-01-24 | 2011-06-29 | Clariant Finance (BVI) Limited | Benzothioxanthene dyes with improved application and toxicological properties |
| CN112110890A (zh) * | 2020-11-04 | 2020-12-22 | 刘燕 | 一种塑料着色剂gg橙及其制备方法 |
-
1971
- 1971-07-10 DE DE2134518A patent/DE2134518C3/de not_active Expired
-
1972
- 1972-07-06 CH CH1015372A patent/CH574437A5/xx not_active IP Right Cessation
- 1972-07-07 GB GB3194372A patent/GB1393956A/en not_active Expired
- 1972-07-07 JP JP6763672A patent/JPS558545B1/ja active Pending
- 1972-07-07 AU AU44332/72A patent/AU461200B2/en not_active Expired
- 1972-07-08 IT IT26803/72A patent/IT962668B/it active
- 1972-07-10 FR FR7224904A patent/FR2145992A5/fr not_active Expired
- 1972-07-10 US US00270257A patent/US3829439A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU461200B2 (en) | 1975-05-22 |
| DE2134518A1 (de) | 1973-01-25 |
| JPS558545B1 (OSRAM) | 1980-03-04 |
| IT962668B (it) | 1973-12-31 |
| GB1393956A (en) | 1975-05-14 |
| US3829439A (en) | 1974-08-13 |
| CH574437A5 (OSRAM) | 1976-04-15 |
| FR2145992A5 (OSRAM) | 1973-02-23 |
| AU4433272A (en) | 1974-01-10 |
| DE2134518B2 (de) | 1978-11-16 |
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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 |