JPS6260423B2 - - Google Patents
Info
- Publication number
- JPS6260423B2 JPS6260423B2 JP53085244A JP8524478A JPS6260423B2 JP S6260423 B2 JPS6260423 B2 JP S6260423B2 JP 53085244 A JP53085244 A JP 53085244A JP 8524478 A JP8524478 A JP 8524478A JP S6260423 B2 JPS6260423 B2 JP S6260423B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- alkyl
- phenyl
- substituted
- 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 5
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 150000002894 organic compounds Chemical class 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- -1 thiazole compound Chemical class 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- FFAXXAIVTXYWMN-UHFFFAOYSA-N methyl 2-cyano-2-(4-phenyl-1,3-thiazol-2-yl)acetate Chemical compound S1C(C(C#N)C(=O)OC)=NC(C=2C=CC=CC=2)=C1 FFAXXAIVTXYWMN-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ANXBVNAZXACCJL-UHFFFAOYSA-N 3-(n-ethyl-4-nitrosoanilino)propanenitrile;hydrochloride Chemical compound Cl.N#CCCN(CC)C1=CC=C(N=O)C=C1 ANXBVNAZXACCJL-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- TVFXOIYPLHTRQR-UHFFFAOYSA-N n,n-dimethyl-4-nitrosoaniline;hydron;chloride Chemical compound Cl.CN(C)C1=CC=C(N=O)C=C1 TVFXOIYPLHTRQR-UHFFFAOYSA-N 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0091—Methine or polymethine dyes, e.g. cyanine dyes having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol
-
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
-
- 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
- C09B55/00—Azomethine dyes
- C09B55/009—Azomethine dyes, the C-atom of the group -C=N- being part of a ring (Image)
-
- 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
- C09B57/04—Isoindoline dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772732221 DE2732221A1 (de) | 1977-07-16 | 1977-07-16 | Organische verbindungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5419974A JPS5419974A (en) | 1979-02-15 |
| JPS6260423B2 true JPS6260423B2 (is") | 1987-12-16 |
Family
ID=6014091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8524478A Granted JPS5419974A (en) | 1977-07-16 | 1978-07-14 | Novel organic compound |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5419974A (is") |
| CH (1) | CH638824A5 (is") |
| DE (1) | DE2732221A1 (is") |
| GB (1) | GB2001094B (is") |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0449516U (is") * | 1990-09-01 | 1992-04-27 | ||
| JPH0733728U (ja) * | 1993-12-03 | 1995-06-23 | 一二 堀内 | 自動車の窓ガラス用霜除けカバ− |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH636116A5 (de) * | 1978-07-28 | 1983-05-13 | Sandoz Ag | Heterocyclische dispersionsfarbstoffe. |
| DE3716656A1 (de) * | 1987-05-19 | 1988-12-01 | Basf Ag | Thienonverbindungen |
| JPH0766168B2 (ja) * | 1988-10-04 | 1995-07-19 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料 |
| JPH02147665A (ja) * | 1988-11-29 | 1990-06-06 | Nippon Kayaku Co Ltd | チアゾール系化合物及びそれを用いる疎水性繊維の染色法 |
| DE3928243A1 (de) * | 1989-08-26 | 1991-02-28 | Basf Ag | Merocyaninartige thiazolfarbstoffe sowie ein verfahren zum thermischen transfer dieser farbstoffe |
| JPH0593453A (ja) * | 1991-09-30 | 1993-04-16 | Tosutemu Sera Kk | アルミサイデイング装置 |
| DE4401912A1 (de) * | 1994-01-24 | 1995-07-27 | Basf Ag | Methinfarbstoffe in der nichtlinearen Optik |
| US5703238A (en) * | 1994-02-02 | 1997-12-30 | Basf Aktiengesellschaft | Preparation of pyridine dyes |
| DE4403083A1 (de) * | 1994-02-02 | 1995-08-03 | Basf Ag | Verfahren zur Herstellung von Pyridinfarbstoffen |
| JPH09512572A (ja) * | 1994-04-28 | 1997-12-16 | ビーエーエスエフ アクチェンゲゼルシャフト | チアゾールメチン染料 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE82748C (is") * | ||||
| DE81509C (is") * | ||||
| DE65402C (de) * | FARBENFABRIKEN VORM. FRIEDR. BAYER & CO. in Elberfeld | Verfahren zur Darstellung gelber Baumwollfarbstoffe aus Dehydrothio - p - toluidin und dessen Homologen | ||
| DE955178C (de) * | 1953-12-23 | 1956-12-27 | Basf Ag | Verfahren zur Herstellung von Farbstoffen |
| DE1045015B (de) * | 1955-11-23 | 1958-11-27 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung von Schwefelfarbstoffen der Dioxazinreihe |
| DE2021899A1 (de) * | 1970-05-05 | 1971-11-25 | Basf Ag | Sulfonsaeuregruppenhaltige Farbstoffe und deren Salze |
-
1977
- 1977-07-16 DE DE19772732221 patent/DE2732221A1/de active Granted
-
1978
- 1978-07-12 CH CH760378A patent/CH638824A5/de not_active IP Right Cessation
- 1978-07-14 GB GB7829856A patent/GB2001094B/en not_active Expired
- 1978-07-14 JP JP8524478A patent/JPS5419974A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0449516U (is") * | 1990-09-01 | 1992-04-27 | ||
| JPH0733728U (ja) * | 1993-12-03 | 1995-06-23 | 一二 堀内 | 自動車の窓ガラス用霜除けカバ− |
Also Published As
| Publication number | Publication date |
|---|---|
| CH638824A5 (de) | 1983-10-14 |
| DE2732221C2 (is") | 1987-10-08 |
| DE2732221A1 (de) | 1979-02-01 |
| JPS5419974A (en) | 1979-02-15 |
| GB2001094B (en) | 1982-02-24 |
| GB2001094A (en) | 1979-01-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6260423B2 (is") | ||
| JP2006052521A (ja) | フルオロスルホニル基を有するモノアゾ染料およびその使用 | |
| JP4005648B2 (ja) | アゾ染料 | |
| JPH02242859A (ja) | ４―クロロチアゾリル含有アゾ分散染料の製法 | |
| JPS604852B2 (ja) | 新規なクマリン系の染料 | |
| KR100275390B1 (ko) | 분산염료 | |
| JPS6221023B2 (is") | ||
| JP2531743B2 (ja) | チエノン化合物 | |
| US4373102A (en) | Isoindoline dyes, their preparation and use | |
| US4299959A (en) | Fluorescent pigments | |
| US3390168A (en) | Disperse dyestuffs | |
| JPH0764988B2 (ja) | アゾ染料の製造方法 | |
| DE2238378B2 (de) | Perinonfarbstoffe und Verfahren zu ihrer Herstellung | |
| DE2237372C3 (de) | Heterocyclische Farbstoffe, ihre Herstellung und ihre Verwendung | |
| KR100296572B1 (ko) | 염료 | |
| US4632983A (en) | Pyridone dyes containing a oxydiazone substituent | |
| US5179207A (en) | Substituted 2-amino-5-maleimido thiophenes and substituted 2-amino-maleimido thiazoles | |
| US4239894A (en) | Thiazole derivatives | |
| JP2854908B2 (ja) | イミド化合物の製造方法 | |
| US4042611A (en) | Water-in-soluble disazo methine compounds | |
| US3985772A (en) | 3-Amidinocoumarin dyes | |
| US4096145A (en) | Naphtholactam derivatives | |
| US4166068A (en) | β,β-Dicyano styrenes | |
| JPS6360793B2 (is") | ||
| US5235047A (en) | Bathochromic azo dyes derived from 2-aminothiophenes and 2-aminothiazoles |