CH617929A5 - - Google Patents
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- Publication number
- CH617929A5 CH617929A5 CH1309276A CH1309276A CH617929A5 CH 617929 A5 CH617929 A5 CH 617929A5 CH 1309276 A CH1309276 A CH 1309276A CH 1309276 A CH1309276 A CH 1309276A CH 617929 A5 CH617929 A5 CH 617929A5
- Authority
- CH
- Switzerland
- Prior art keywords
- reaction
- triazine
- acid
- sulfonic acid
- continuously
- Prior art date
Links
- 238000006243 chemical reaction Methods 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
- 238000000034 method Methods 0.000 description 17
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 14
- 239000000376 reactant Substances 0.000 description 12
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 7
- 150000004027 organic amino compounds Chemical class 0.000 description 7
- 238000001816 cooling Methods 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 2
- HEAHMJLHQCESBZ-UHFFFAOYSA-N 2,5-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(N)C(S(O)(=O)=O)=C1 HEAHMJLHQCESBZ-UHFFFAOYSA-N 0.000 description 2
- RXNKCIBVUNMMAD-UHFFFAOYSA-N 4-[9-(4-amino-3-fluorophenyl)fluoren-9-yl]-2-fluoroaniline Chemical compound C1=C(F)C(N)=CC=C1C1(C=2C=C(F)C(N)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 RXNKCIBVUNMMAD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- -1 acylated amino compound Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- VOPSFYWMOIKYEM-UHFFFAOYSA-N 2,5-diaminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=C(N)C=C1S(O)(=O)=O VOPSFYWMOIKYEM-UHFFFAOYSA-N 0.000 description 1
- PMWXDMJNCNZHAD-UHFFFAOYSA-N 2-[[4-fluoro-6-(2-sulfoanilino)-1,3,5-triazin-2-yl]amino]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1NC1=NC(F)=NC(NC=2C(=CC=CC=2)S(O)(=O)=O)=N1 PMWXDMJNCNZHAD-UHFFFAOYSA-N 0.000 description 1
- MJNYPLCGWXFYPD-UHFFFAOYSA-N 2-amino-5-sulfobenzoic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1C(O)=O MJNYPLCGWXFYPD-UHFFFAOYSA-N 0.000 description 1
- DGUFAFFRGZKNHB-UHFFFAOYSA-N 3-[(4,6-difluoro-1,3,5-triazin-2-yl)amino]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(NC=2N=C(F)N=C(F)N=2)=C1 DGUFAFFRGZKNHB-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- YADSWTKOIHUSDX-UHFFFAOYSA-N 4,6-diaminobenzene-1,3-disulfonic acid Chemical compound NC1=CC(N)=C(S(O)(=O)=O)C=C1S(O)(=O)=O YADSWTKOIHUSDX-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 1
- JXZGTFLJFKLVAX-UHFFFAOYSA-N 5-amino-2-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C=C1S(O)(=O)=O JXZGTFLJFKLVAX-UHFFFAOYSA-N 0.000 description 1
- BRKFTWHPLMMNHF-UHFFFAOYSA-N 5-amino-2-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C=C1S(O)(=O)=O BRKFTWHPLMMNHF-UHFFFAOYSA-N 0.000 description 1
- GBWNQBBVSVGAAL-UHFFFAOYSA-N 5-aminobenzene-1,3-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(S(O)(=O)=O)=C1 GBWNQBBVSVGAAL-UHFFFAOYSA-N 0.000 description 1
- UWPJYQYRSWYIGZ-UHFFFAOYSA-N 5-aminonaphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC=CC2=C1 UWPJYQYRSWYIGZ-UHFFFAOYSA-N 0.000 description 1
- KZCSUEYBKAPKNH-UHFFFAOYSA-N 6-aminonaphthalene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KZCSUEYBKAPKNH-UHFFFAOYSA-N 0.000 description 1
- YUNBHHWDQDGWHC-UHFFFAOYSA-N 6-aminonaphthalene-1-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=CC(N)=CC=C21 YUNBHHWDQDGWHC-UHFFFAOYSA-N 0.000 description 1
- OKAUOXITMZTUOJ-UHFFFAOYSA-N 7-aminonaphthalene-2-sulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 OKAUOXITMZTUOJ-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/44—One nitrogen atom with halogen atoms attached to the two other ring carbon atoms
-
- 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
- C09B62/04—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 to a triazine ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1309276A CH617929A5 (ja) | 1976-10-15 | 1976-10-15 | |
| US05/841,865 US4189576A (en) | 1976-10-15 | 1977-10-13 | Process for monoacylating water-soluble organic amino compounds |
| FR7730841A FR2367755A1 (fr) | 1976-10-15 | 1977-10-13 | Procede pou |
| DE19772746109 DE2746109A1 (de) | 1976-10-15 | 1977-10-13 | Verfahren zur monoacylierung wasserloeslicher organischer aminoverbindungen |
| CA288,661A CA1094054A (en) | 1976-10-15 | 1977-10-13 | Process for monoacylating water-soluble organic amino compounds |
| CS776702A CS198271B2 (en) | 1976-10-15 | 1977-10-14 | Method of monoacylation of water insoluble organic amino compounds |
| ES463531A ES463531A1 (es) | 1976-10-15 | 1977-10-14 | Procedimiento para la preparacion de aminocompuestos organi-cos solubles en agua monoacilados. |
| BE181738A BE859725A (fr) | 1976-10-15 | 1977-10-14 | Procede pour monoacyler des composes amines organiques solubles dans l'eau |
| BR7706894A BR7706894A (pt) | 1976-10-15 | 1977-10-14 | Processo para monoacilacao de aminocompostos organicos hidrossoluveis |
| GB42886/77A GB1551202A (en) | 1976-10-15 | 1977-10-14 | Process for monoacylating water-soluble organic amino comppounds |
| JP12302077A JPS5350186A (en) | 1976-10-15 | 1977-10-15 | Monoacylation of water soluble organic amino compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1309276A CH617929A5 (ja) | 1976-10-15 | 1976-10-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH617929A5 true CH617929A5 (ja) | 1980-06-30 |
Family
ID=4389233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1309276A CH617929A5 (ja) | 1976-10-15 | 1976-10-15 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4189576A (ja) |
| JP (1) | JPS5350186A (ja) |
| BE (1) | BE859725A (ja) |
| BR (1) | BR7706894A (ja) |
| CA (1) | CA1094054A (ja) |
| CH (1) | CH617929A5 (ja) |
| CS (1) | CS198271B2 (ja) |
| DE (1) | DE2746109A1 (ja) |
| ES (1) | ES463531A1 (ja) |
| FR (1) | FR2367755A1 (ja) |
| GB (1) | GB1551202A (ja) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3010502C2 (de) * | 1980-03-19 | 1982-07-01 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Dihalogentriazinyl-aminonaphthol-Verbindungen |
| EP0172790B1 (de) * | 1984-08-21 | 1992-07-29 | Ciba-Geigy Ag | Verfahren zur kontinuierlichen Umsetzung von Cyanurfluorid mit Aminonaphtholsulfonsäuren |
| EP0228348B1 (de) * | 1985-12-24 | 1989-11-02 | Ciba-Geigy Ag | Verfahren zur Herstellung von Reaktivfarbstoffen |
| DE3727253A1 (de) * | 1987-08-15 | 1989-02-23 | Bayer Ag | Verfahren zur monoacylierung wasserloeslicher organischer aminoverbindungen mit 2,4,6-trifluortriazin in waessrigem medium |
| DE4016159A1 (de) * | 1990-05-19 | 1991-11-21 | Bayer Ag | Verfahren zur kontinuierlichen umsetzung von cyanurfluorid mit aminen sowie reaktor zur durchfuehrung des verfahrens |
| DE4100513A1 (de) * | 1991-01-10 | 1992-07-16 | Bayer Ag | Verbessertes verfahren zur herstellung eines substituierten 1-amino-2-sulfonaphthalins |
| DE4137292A1 (de) * | 1991-11-13 | 1993-05-19 | Bayer Ag | Verfahren zur kontinuierlichen umsetzung von difluortriazinyl-verbindungen mit aminen |
| DE4137291A1 (de) * | 1991-11-13 | 1993-05-19 | Bayer Ag | Verfahren zur kontinuierlichen umsetzung von halogenpyrimidinen mit aminen |
| EP0546993A1 (de) * | 1991-12-09 | 1993-06-16 | Ciba-Geigy Ag | Wasserlöschliche Triazinderivate zur photochemischen und thermischen Stabilisierung von Polyamidfasermaterialien |
| AU688268B2 (en) * | 1992-08-12 | 1998-03-12 | Clariant Finance (Bvi) Limited | Method of increasing the spf rating and compounds suitable for increasing the spf rating of fibre or fabric |
| DE4416015A1 (de) * | 1994-05-06 | 1995-11-09 | Hoechst Ag | Verfahren zur kontinuierlichen Umsetzung von aminogruppenhaltigen organischen Farbstoffen mit Trifluortriazin |
| DE19548429A1 (de) | 1995-12-22 | 1997-06-26 | Dystar Textilfarben Gmbh & Co | Wasserlösliche Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19750701A1 (de) * | 1997-11-15 | 1999-05-20 | Dystar Textilfarben Gmbh & Co | Verfahren zur Umsetzung von fluorsubstituierten Heterocyclen mit Aminen in Gegenwart von Phasentransfer-Katalysatoren |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH554403A (de) * | 1969-07-11 | 1974-09-30 | Ciba Geigy Ag | Verfahren zur herstellung von faserreaktiven azofarbstoffen. |
| US3945989A (en) * | 1969-07-11 | 1976-03-23 | Ciba-Geigy Ag | Fluoro triazine containing water insoluble azo dyestuff |
| CH626650A5 (ja) * | 1974-12-18 | 1981-11-30 | Ciba Geigy Ag | |
| ES446171A1 (es) * | 1975-03-20 | 1977-10-16 | Ciba Geigy | Procedimiento para la preparacion de colorantes fibrorreac- tivos. |
-
1976
- 1976-10-15 CH CH1309276A patent/CH617929A5/de not_active IP Right Cessation
-
1977
- 1977-10-13 FR FR7730841A patent/FR2367755A1/fr active Granted
- 1977-10-13 CA CA288,661A patent/CA1094054A/en not_active Expired
- 1977-10-13 DE DE19772746109 patent/DE2746109A1/de active Granted
- 1977-10-13 US US05/841,865 patent/US4189576A/en not_active Expired - Lifetime
- 1977-10-14 ES ES463531A patent/ES463531A1/es not_active Expired
- 1977-10-14 CS CS776702A patent/CS198271B2/cs unknown
- 1977-10-14 GB GB42886/77A patent/GB1551202A/en not_active Expired
- 1977-10-14 BR BR7706894A patent/BR7706894A/pt unknown
- 1977-10-14 BE BE181738A patent/BE859725A/xx unknown
- 1977-10-15 JP JP12302077A patent/JPS5350186A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| BR7706894A (pt) | 1978-07-18 |
| CS198271B2 (en) | 1980-05-30 |
| FR2367755A1 (fr) | 1978-05-12 |
| JPH0248552B2 (ja) | 1990-10-25 |
| US4189576A (en) | 1980-02-19 |
| JPS5350186A (en) | 1978-05-08 |
| BE859725A (fr) | 1978-04-14 |
| CA1094054A (en) | 1981-01-20 |
| FR2367755B1 (ja) | 1980-08-08 |
| GB1551202A (en) | 1979-08-22 |
| DE2746109A1 (de) | 1978-04-20 |
| DE2746109C2 (ja) | 1988-10-27 |
| ES463531A1 (es) | 1978-12-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |