JPH037705B2 - - Google Patents
Info
- Publication number
- JPH037705B2 JPH037705B2 JP56096082A JP9608281A JPH037705B2 JP H037705 B2 JPH037705 B2 JP H037705B2 JP 56096082 A JP56096082 A JP 56096082A JP 9608281 A JP9608281 A JP 9608281A JP H037705 B2 JPH037705 B2 JP H037705B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- coupling
- azo
- basic lithium
- 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 - Lifetime
Links
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 25
- 230000008878 coupling Effects 0.000 claims description 21
- 238000010168 coupling process Methods 0.000 claims description 21
- 238000005859 coupling reaction Methods 0.000 claims description 21
- 238000005917 acylation reaction Methods 0.000 claims description 17
- 150000002642 lithium compounds Chemical class 0.000 claims description 17
- -1 2,4-difluoro-5-chloropyrimidin-6-yl group Chemical group 0.000 claims description 14
- 230000010933 acylation Effects 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000000985 reactive dye Substances 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- WAVYAFBQOXCGSZ-UHFFFAOYSA-N 2-fluoropyrimidine Chemical group FC1=NC=CC=N1 WAVYAFBQOXCGSZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 3
- 229910003002 lithium salt Inorganic materials 0.000 claims description 3
- 159000000002 lithium salts Chemical class 0.000 claims description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 2
- HIMMCCJEMMCUJS-UHFFFAOYSA-N 4-fluorotriazine Chemical compound FC1=CC=NN=N1 HIMMCCJEMMCUJS-UHFFFAOYSA-N 0.000 claims description 2
- ZLNPDTOTEVIMMY-UHFFFAOYSA-N 5-chloropyrimidine Chemical compound ClC1=CN=CN=C1 ZLNPDTOTEVIMMY-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000975 dye Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 12
- 238000006193 diazotization reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- GOYNRDSJTYLXBU-UHFFFAOYSA-N 5-chloro-2,4,6-trifluoropyrimidine Chemical compound FC1=NC(F)=C(Cl)C(F)=N1 GOYNRDSJTYLXBU-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 238000002036 drum drying Methods 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- ZLCIWBUBLMHRSD-UHFFFAOYSA-N 2,3-dichloro-4,6-difluoropyridine Chemical compound FC1=CC(F)=C(Cl)C(Cl)=N1 ZLCIWBUBLMHRSD-UHFFFAOYSA-N 0.000 description 1
- NTSYSQNAPGMSIH-UHFFFAOYSA-N 2,4,6-trifluoropyrimidine Chemical compound FC1=CC(F)=NC(F)=N1 NTSYSQNAPGMSIH-UHFFFAOYSA-N 0.000 description 1
- KTVWISLTJPDQQX-UHFFFAOYSA-N 2-amino-5-(aminomethyl)naphthalene-1-sulfonic acid Chemical compound NC1=CC=C2C(CN)=CC=CC2=C1S(O)(=O)=O KTVWISLTJPDQQX-UHFFFAOYSA-N 0.000 description 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- BUVOCOQOYNGMCO-UHFFFAOYSA-N 4-benzamido-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound C=12C(O)=CC(S(O)(=O)=O)=CC2=C(S(O)(=O)=O)C=CC=1NC(=O)C1=CC=CC=C1 BUVOCOQOYNGMCO-UHFFFAOYSA-N 0.000 description 1
- TZBROGJRQUABOK-UHFFFAOYSA-N 4-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 TZBROGJRQUABOK-UHFFFAOYSA-N 0.000 description 1
- RMULVUFPLMJWOK-UHFFFAOYSA-N 5-chloro-2,4-difluoro-6-methylpyrimidine Chemical compound CC1=NC(F)=NC(F)=C1Cl RMULVUFPLMJWOK-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- DBZLAIRBFBGCNR-UHFFFAOYSA-N FN1NC(=CC(=N1)F)N Chemical compound FN1NC(=CC(=N1)F)N DBZLAIRBFBGCNR-UHFFFAOYSA-N 0.000 description 1
- OFVPOHAGKURVLJ-UHFFFAOYSA-N FN1NC(=CC(=N1)F)NC Chemical compound FN1NC(=CC(=N1)F)NC OFVPOHAGKURVLJ-UHFFFAOYSA-N 0.000 description 1
- BNDNKUIOGYCZRD-UHFFFAOYSA-N FN1NC(=CC(=N1)F)NCCO Chemical compound FN1NC(=CC(=N1)F)NCCO BNDNKUIOGYCZRD-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/022—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring the heterocyclic ring being alternatively specified
- C09B62/026—Azo dyes
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 |
|---|---|---|---|
| DE19803023920 DE3023920A1 (de) | 1980-06-26 | 1980-06-26 | Verfahren zur herstellung von azo-reaktivfarbstoffen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5731960A JPS5731960A (en) | 1982-02-20 |
| JPH037705B2 true JPH037705B2 (US07709020-20100504-C00041.png) | 1991-02-04 |
Family
ID=6105508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9608281A Granted JPS5731960A (en) | 1980-06-26 | 1981-06-23 | Manufacture of azo reactive dye |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0043927B1 (US07709020-20100504-C00041.png) |
| JP (1) | JPS5731960A (US07709020-20100504-C00041.png) |
| DE (2) | DE3023920A1 (US07709020-20100504-C00041.png) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3247352A1 (de) * | 1982-12-22 | 1984-06-28 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von azofarbstoffen |
| EP0122881B1 (de) * | 1983-04-15 | 1986-08-13 | Ciba-Geigy Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
| JPH0213071Y2 (US07709020-20100504-C00041.png) * | 1985-10-31 | 1990-04-11 | ||
| DE3939536A1 (de) * | 1989-11-30 | 1991-06-06 | Bayer Ag | Azoreaktivfarbstoffe |
| DE4100513A1 (de) * | 1991-01-10 | 1992-07-16 | Bayer Ag | Verbessertes verfahren zur herstellung eines substituierten 1-amino-2-sulfonaphthalins |
| DE4137291A1 (de) * | 1991-11-13 | 1993-05-19 | Bayer Ag | Verfahren zur kontinuierlichen umsetzung von halogenpyrimidinen mit aminen |
| EP1469039A1 (de) * | 2003-04-17 | 2004-10-20 | Clariant International Ltd. | Faserreaktive Azofarbstoffe |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5411933A (en) * | 1977-06-29 | 1979-01-29 | Bayer Ag | Reactive dyestuff |
| JPS54139934A (en) * | 1978-04-19 | 1979-10-30 | Basf Ag | Reactive dye |
| JPS5512183A (en) * | 1978-07-06 | 1980-01-28 | Bayer Ag | Reactive azo dye |
| JPS5516009A (en) * | 1978-07-20 | 1980-02-04 | Nippon Kagaku Kogyosho:Kk | Trisazo dye solution composition |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH517159A (de) * | 1964-10-12 | 1971-12-31 | Sandoz Ag | Verfahren zur Herstellung von Reaktivfarbstoffen |
| DE2401762A1 (de) * | 1974-01-15 | 1975-07-24 | Ici Ltd | Verfahren zur herstellung von stilbenazofarbstoffen |
-
1980
- 1980-06-26 DE DE19803023920 patent/DE3023920A1/de not_active Withdrawn
-
1981
- 1981-06-15 DE DE8181104599T patent/DE3163613D1/de not_active Expired
- 1981-06-15 EP EP81104599A patent/EP0043927B1/de not_active Expired
- 1981-06-23 JP JP9608281A patent/JPS5731960A/ja active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5411933A (en) * | 1977-06-29 | 1979-01-29 | Bayer Ag | Reactive dyestuff |
| JPS54139934A (en) * | 1978-04-19 | 1979-10-30 | Basf Ag | Reactive dye |
| JPS5512183A (en) * | 1978-07-06 | 1980-01-28 | Bayer Ag | Reactive azo dye |
| JPS5516009A (en) * | 1978-07-20 | 1980-02-04 | Nippon Kagaku Kogyosho:Kk | Trisazo dye solution composition |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0043927B1 (de) | 1984-05-16 |
| DE3163613D1 (en) | 1984-06-20 |
| EP0043927A2 (de) | 1982-01-20 |
| EP0043927A3 (en) | 1982-05-26 |
| DE3023920A1 (de) | 1982-01-21 |
| JPS5731960A (en) | 1982-02-20 |
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