CH628080A5 - Verfahren zur herstellung von farbstoffen der cumarinreihe. - Google Patents
Verfahren zur herstellung von farbstoffen der cumarinreihe. Download PDFInfo
- Publication number
- CH628080A5 CH628080A5 CH829776A CH829776A CH628080A5 CH 628080 A5 CH628080 A5 CH 628080A5 CH 829776 A CH829776 A CH 829776A CH 829776 A CH829776 A CH 829776A CH 628080 A5 CH628080 A5 CH 628080A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- alkyl
- nitrogen
- optionally substituted
- alkoxy
- Prior art date
Links
- 239000003086 colorant Substances 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 238000004043 dyeing Methods 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- -1 methoxy, ethoxy Chemical group 0.000 claims description 5
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000005521 carbonamide group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 238000004040 coloring Methods 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- XFVZSRRZZNLWBW-UHFFFAOYSA-N 4-(Diethylamino)salicylaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C(O)=C1 XFVZSRRZZNLWBW-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- KURCTZNCAHYQOV-UHFFFAOYSA-N 4-(dimethylamino)-2-hydroxybenzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C(O)=C1 KURCTZNCAHYQOV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- BNGLGOBSEGPTKW-UHFFFAOYSA-N diethyl 2-iminopropanedioate;hydrochloride Chemical compound Cl.CCOC(=O)C(=N)C(=O)OCC BNGLGOBSEGPTKW-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- ILAXBOIRSPXAMM-UHFFFAOYSA-N methyl n-aminocarbamodithioate Chemical compound CSC(=S)NN ILAXBOIRSPXAMM-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000010023 transfer printing Methods 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/02—Coumarine dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/003—Transfer printing
- D06P5/004—Transfer printing using subliming dyes
- D06P5/006—Transfer printing using subliming dyes using specified dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752529434 DE2529434C3 (de) | 1975-07-02 | 1975-07-02 | Farbstoffe der Cumarinreihe und ihre Verwendung |
| DE19752553294 DE2553294A1 (de) | 1975-11-27 | 1975-11-27 | Farbstoffe der cumarinreihe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH628080A5 true CH628080A5 (de) | 1982-02-15 |
Family
ID=25769100
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH829776A CH628080A5 (de) | 1975-07-02 | 1976-06-29 | Verfahren zur herstellung von farbstoffen der cumarinreihe. |
| CH1046178A CH629238A5 (de) | 1975-07-02 | 1978-10-09 | Verfahren zur herstellung von farbstoffen der cumarinreihe. |
| CH528281A CH629524A5 (de) | 1975-07-02 | 1981-08-14 | Verfahren zur herstellung von farbstoffen der cumarinreihe. |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1046178A CH629238A5 (de) | 1975-07-02 | 1978-10-09 | Verfahren zur herstellung von farbstoffen der cumarinreihe. |
| CH528281A CH629524A5 (de) | 1975-07-02 | 1981-08-14 | Verfahren zur herstellung von farbstoffen der cumarinreihe. |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4055568A (enExample) |
| JP (1) | JPS604852B2 (enExample) |
| CH (3) | CH628080A5 (enExample) |
| FR (1) | FR2316293A1 (enExample) |
| GB (1) | GB1543933A (enExample) |
| IT (1) | IT1062591B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4146712A (en) * | 1976-03-11 | 1979-03-27 | Ciba-Geigy Corporation | Process for the manufacture of coumarin dyes |
| LU78311A1 (de) * | 1977-10-13 | 1979-06-01 | Ciba Geigy Ag | Neue cumarinfarbstoffe,deren herstellung und verwendung |
| DE2807761A1 (de) * | 1978-02-23 | 1979-08-30 | Basf Ag | Cumarinderivate |
| US4547579A (en) * | 1978-10-10 | 1985-10-15 | Ciba-Geigy Corporation | Substituted benzopyran compounds |
| DE2925546A1 (de) * | 1979-06-25 | 1981-01-15 | Bayer Ag | Cumarinverbindungen sowie deren herstellung und verwendung als farbstoffe |
| DE3021947A1 (de) * | 1980-06-12 | 1982-01-14 | Bayer Ag, 5090 Leverkusen | Farbstoffpraeparation sowie deren verwendung als warn- und signalfarbe |
| JPS57123677A (en) * | 1981-01-26 | 1982-08-02 | Tokyo Shibaura Electric Co | Ceramic insulating cylinder for high temperature fluid |
| JPS57152906A (en) * | 1981-03-18 | 1982-09-21 | Mitsubishi Heavy Ind Ltd | Method of casting ceramic |
| JPS5813488A (ja) * | 1981-07-14 | 1983-01-25 | Kobe Steel Ltd | 金属クラツドセラミツクパイプの製造方法 |
| JPS6441852U (enExample) * | 1987-09-02 | 1989-03-13 | ||
| JPS6477531A (en) * | 1987-09-18 | 1989-03-23 | Daido Ind | Assembly of metal holder and ceramics |
| US4882412A (en) * | 1987-11-30 | 1989-11-21 | Eastman Kodak Company | Polyester polymer containing the residue of the UV absorbing benzopyran compound and shaped articles produced therefrom |
| US4892922A (en) * | 1987-11-30 | 1990-01-09 | Eastman Kodak Company | Polyester polymer containing the residue of a benzopyran colorant compound and shaped articles produced therefrom |
| US5098820A (en) * | 1990-05-07 | 1992-03-24 | Eastman Kodak Company | Solid particle dispersions of filter dyes for photographic elements |
| DE4126244A1 (de) * | 1991-08-08 | 1993-02-11 | Bayer Ag | Massefaerben von kunststoffen |
| FR2683822B1 (fr) * | 1991-11-16 | 1994-12-23 | Sandoz Sa | Nouveaux melanges de colorants de dispersion. |
| CN119504720B (zh) * | 2024-11-26 | 2025-09-30 | 大连大学 | 一种基于香豆素和呋喃杂环的荧光金属缓蚀剂及其制备方法和应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH465551A (de) * | 1964-11-13 | 1969-01-15 | Geigy Ag J R | Verfahren zum Färben oder Bedrucken von Textilfasern aus linearen Polyestern, Celluloseestern oder synthetischen Polyamiden mit Dispersionsfarbstoffen |
| CH473197A (de) * | 1966-07-22 | 1969-05-31 | Geigy Ag J R | Verfahren zur Herstellung von kationischen Cumarinimidfarbstoffen |
| CH565228A5 (enExample) * | 1972-04-18 | 1975-08-15 | Ciba Geigy Ag |
-
1976
- 1976-06-04 GB GB23125/76A patent/GB1543933A/en not_active Expired
- 1976-06-07 US US05/693,187 patent/US4055568A/en not_active Expired - Lifetime
- 1976-06-29 CH CH829776A patent/CH628080A5/de not_active IP Right Cessation
- 1976-06-29 JP JP51076108A patent/JPS604852B2/ja not_active Expired
- 1976-07-01 FR FR7620072A patent/FR2316293A1/fr active Granted
- 1976-07-01 IT IT50235/76A patent/IT1062591B/it active
-
1978
- 1978-10-09 CH CH1046178A patent/CH629238A5/de not_active IP Right Cessation
-
1981
- 1981-08-14 CH CH528281A patent/CH629524A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS604852B2 (ja) | 1985-02-07 |
| US4055568A (en) | 1977-10-25 |
| CH629524A5 (de) | 1982-04-30 |
| FR2316293B1 (enExample) | 1979-06-22 |
| GB1543933A (en) | 1979-04-11 |
| CH629238A5 (de) | 1982-04-15 |
| JPS526732A (en) | 1977-01-19 |
| IT1062591B (it) | 1984-10-20 |
| FR2316293A1 (fr) | 1977-01-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |