DE2741395A1 - Verfahren zur herstellung von quartaeren ammoniumsalzen von organischen farbstoffbasen - Google Patents
Verfahren zur herstellung von quartaeren ammoniumsalzen von organischen farbstoffbasenInfo
- Publication number
- DE2741395A1 DE2741395A1 DE19772741395 DE2741395A DE2741395A1 DE 2741395 A1 DE2741395 A1 DE 2741395A1 DE 19772741395 DE19772741395 DE 19772741395 DE 2741395 A DE2741395 A DE 2741395A DE 2741395 A1 DE2741395 A1 DE 2741395A1
- Authority
- DE
- Germany
- Prior art keywords
- alkylating agent
- preparation
- methyl
- reaction
- ammonium salts
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 23
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000003863 ammonium salts Chemical class 0.000 title 1
- 229940100198 alkylating agent Drugs 0.000 claims description 26
- 239000002168 alkylating agent Substances 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000007787 solid Substances 0.000 claims description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 12
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 11
- TYRCKEFIYKISNH-UHFFFAOYSA-N 1-(pyridin-3-yldiazenyl)naphthalen-2-ol Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC1=CC=CN=C1 TYRCKEFIYKISNH-UHFFFAOYSA-N 0.000 claims description 8
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 6
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 claims description 6
- 239000011780 sodium chloride Substances 0.000 claims description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 5
- AVPFTROGVGTTEC-UHFFFAOYSA-N 4-[(6-methoxy-1,3-benzothiazol-2-yl)diazenyl]-n,n-dimethylaniline Chemical compound S1C2=CC(OC)=CC=C2N=C1N=NC1=CC=C(N(C)C)C=C1 AVPFTROGVGTTEC-UHFFFAOYSA-N 0.000 claims description 4
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 229920001353 Dextrin Polymers 0.000 claims description 3
- 239000004375 Dextrin Substances 0.000 claims description 3
- 235000019425 dextrin Nutrition 0.000 claims description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
- 229940102396 methyl bromide Drugs 0.000 claims description 2
- 239000012022 methylating agents Substances 0.000 claims description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 2
- LOMVENUNSWAXEN-NUQCWPJISA-N dimethyl oxalate Chemical group CO[14C](=O)[14C](=O)OC LOMVENUNSWAXEN-NUQCWPJISA-N 0.000 claims 1
- 229940050176 methyl chloride Drugs 0.000 claims 1
- 239000000975 dye Substances 0.000 description 17
- 239000002585 base Substances 0.000 description 13
- 238000005956 quaternization reaction Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 229920002972 Acrylic fiber Polymers 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 3
- KMAQZIILEGKYQZ-UHFFFAOYSA-N 1-chloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1 KMAQZIILEGKYQZ-UHFFFAOYSA-N 0.000 description 2
- -1 2- (p-Dimethylaminophenylazo) -6-methoxybenzotriazole Chemical compound 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- MZZYWXZNOCHWAM-UHFFFAOYSA-N 1-[(1-methylpyridin-1-ium-3-yl)hydrazinylidene]naphthalen-2-one;methyl sulfate Chemical compound COS([O-])(=O)=O.C[N+]1=CC=CC(N\N=C/2C3=CC=CC=C3C=CC\2=O)=C1 MZZYWXZNOCHWAM-UHFFFAOYSA-N 0.000 description 1
- UWLHSHAHTBJTBA-UHFFFAOYSA-N 1-iodooctane Chemical compound CCCCCCCCI UWLHSHAHTBJTBA-UHFFFAOYSA-N 0.000 description 1
- CHZXTOCAICMPQR-UHFFFAOYSA-N 2-(2-bromoethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCBr)C(=O)C2=C1 CHZXTOCAICMPQR-UHFFFAOYSA-N 0.000 description 1
- BFXMUSWJDNJMQA-UHFFFAOYSA-N 4-methylbenzenesulfonate;1-[(1-methylpyridin-1-ium-3-yl)hydrazinylidene]naphthalen-2-one Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C[N+]1=CC=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1 BFXMUSWJDNJMQA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 229940045681 other alkylating agent in atc Drugs 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 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
- C09B44/00—Azo dyes containing onium groups
- C09B44/005—Special process features in the quaternization reaction
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/724,509 US4081436A (en) | 1976-09-20 | 1976-09-20 | Process for dry quaternization of azo compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2741395A1 true DE2741395A1 (de) | 1978-03-23 |
Family
ID=24910705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772741395 Pending DE2741395A1 (de) | 1976-09-20 | 1977-09-14 | Verfahren zur herstellung von quartaeren ammoniumsalzen von organischen farbstoffbasen |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4081436A (enExample) |
| JP (1) | JPS5337731A (enExample) |
| DE (1) | DE2741395A1 (enExample) |
| FR (1) | FR2364953A1 (enExample) |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA556218A (en) * | 1958-04-22 | Baumann Hans | Production of basic azo dyestuffs | |
| US2480355A (en) * | 1949-08-30 | Aikylene dihalide salts of n-dialktl | ||
| US2650251A (en) * | 1951-02-28 | 1953-08-25 | Merck & Co Inc | Bactericidal compounds |
| US2933530A (en) * | 1955-11-24 | 1960-04-19 | Philips Corp | Method of producing quaternary ammonium compounds |
| US3102839A (en) * | 1960-03-04 | 1963-09-03 | West Laboratories Inc | Germicidal compositions |
| DE1250575B (de) * | 1960-11-30 | 1967-09-21 | Badische Anilin &. Soda Fabrik Aktiengesellschaft, Ludwigshafen/Rhem | Verfahren zur Herstel lung von Diazapolymethmfarbstoffen |
| US3312681A (en) * | 1961-11-10 | 1967-04-04 | American Cyanamid Co | Cationic 1-alkyl-3-(2-hydroxy-1-naphthylazo) pyridinium dyes |
| BE629950A (enExample) * | 1962-03-23 | |||
| US3401158A (en) * | 1965-10-22 | 1968-09-10 | Eastman Kodak Co | Cationic heterocyclic disazo dyes for textile fibers |
| US3956271A (en) * | 1969-01-20 | 1976-05-11 | Sandoz Ltd. | Process for the production of concentrated solutions of cationic azo dyes |
-
1976
- 1976-09-20 US US05/724,509 patent/US4081436A/en not_active Expired - Lifetime
-
1977
- 1977-09-14 DE DE19772741395 patent/DE2741395A1/de active Pending
- 1977-09-20 JP JP11227177A patent/JPS5337731A/ja active Granted
- 1977-09-20 FR FR7728348A patent/FR2364953A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| FR2364953A1 (fr) | 1978-04-14 |
| JPS616862B2 (enExample) | 1986-03-01 |
| JPS5337731A (en) | 1978-04-07 |
| US4081436A (en) | 1978-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |