DE2308724C3 - Verfahren zur Herstellung von 2,2',4,4'-Tetraamino-5,5'-diniethyltriphenylmethan - Google Patents
Verfahren zur Herstellung von 2,2',4,4'-Tetraamino-5,5'-diniethyltriphenylmethanInfo
- Publication number
- DE2308724C3 DE2308724C3 DE19732308724 DE2308724A DE2308724C3 DE 2308724 C3 DE2308724 C3 DE 2308724C3 DE 19732308724 DE19732308724 DE 19732308724 DE 2308724 A DE2308724 A DE 2308724A DE 2308724 C3 DE2308724 C3 DE 2308724C3
- Authority
- DE
- Germany
- Prior art keywords
- water
- tdtm
- reactants
- acid
- tetraamino
- 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
- 238000000034 method Methods 0.000 title claims description 27
- 238000002360 preparation method Methods 0.000 title claims description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 9
- 239000003995 emulsifying agent Substances 0.000 claims description 8
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000000853 adhesive Substances 0.000 claims description 5
- 230000001070 adhesive effect Effects 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 3
- HJCUTNIGJHJGCF-UHFFFAOYSA-N 9,10-dihydroacridine Chemical compound C1=CC=C2CC3=CC=CC=C3NC2=C1 HJCUTNIGJHJGCF-UHFFFAOYSA-N 0.000 claims 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims 2
- 239000002243 precursor Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- CDMGNVWZXRKJNS-UHFFFAOYSA-N 2-benzylphenol Chemical class OC1=CC=CC=C1CC1=CC=CC=C1 CDMGNVWZXRKJNS-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000999 acridine dye Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- DYFXGORUJGZJCA-UHFFFAOYSA-N phenylmethanediamine Chemical compound NC(N)C1=CC=CC=C1 DYFXGORUJGZJCA-UHFFFAOYSA-N 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- 238000010626 work up procedure 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
- C09B11/14—Preparation from aromatic aldehydes, aromatic carboxylic acids or derivatives thereof and aromatic amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732308724 DE2308724C3 (de) | 1973-02-22 | 1973-02-22 | Verfahren zur Herstellung von 2,2',4,4'-Tetraamino-5,5'-diniethyltriphenylmethan |
| CA192,572A CA1014173A (en) | 1973-02-22 | 1974-02-14 | Process for the production of condensation prodcuts |
| NL7402267A NL7402267A (enExample) | 1973-02-22 | 1974-02-19 | |
| AU65760/74A AU6576074A (en) | 1973-02-22 | 1974-02-19 | Condensation of aldehydes with amines |
| IT4853974A IT1008895B (it) | 1973-02-22 | 1974-02-20 | Procedimento per ottenere prodotti di condensazione di aldeidi con ammine |
| BR124574A BR7401245D0 (pt) | 1973-02-22 | 1974-02-20 | Processo para a preparacao de produtos de condensacao |
| CH236574A CH593908A5 (enExample) | 1973-02-22 | 1974-02-20 | |
| IE34974A IE38913B1 (en) | 1973-02-22 | 1974-02-21 | Process for the preparation of an aromatic condensation product containing primary amino groups |
| BE141215A BE811379A (fr) | 1973-02-22 | 1974-02-21 | Procede de preparation de produits de condensation d'amines aromatiques avec des aldehydes hydrophobes |
| ES423480A ES423480A1 (es) | 1973-02-22 | 1974-02-21 | Procedimiento para la obtencion de productos de condensa- cion. |
| FR7406196A FR2219149B1 (enExample) | 1973-02-22 | 1974-02-22 | |
| JP2063974A JPS49115195A (enExample) | 1973-02-22 | 1974-02-22 | |
| GB822074A GB1423096A (en) | 1973-02-22 | 1974-02-22 | Process for the preparation of an aromatic condensation product containing primary amino groups |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732308724 DE2308724C3 (de) | 1973-02-22 | 1973-02-22 | Verfahren zur Herstellung von 2,2',4,4'-Tetraamino-5,5'-diniethyltriphenylmethan |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2308724A1 DE2308724A1 (de) | 1974-09-12 |
| DE2308724B2 DE2308724B2 (de) | 1977-10-27 |
| DE2308724C3 true DE2308724C3 (de) | 1978-06-08 |
Family
ID=5872721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732308724 Expired DE2308724C3 (de) | 1973-02-22 | 1973-02-22 | Verfahren zur Herstellung von 2,2',4,4'-Tetraamino-5,5'-diniethyltriphenylmethan |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS49115195A (enExample) |
| AU (1) | AU6576074A (enExample) |
| BE (1) | BE811379A (enExample) |
| BR (1) | BR7401245D0 (enExample) |
| CA (1) | CA1014173A (enExample) |
| CH (1) | CH593908A5 (enExample) |
| DE (1) | DE2308724C3 (enExample) |
| ES (1) | ES423480A1 (enExample) |
| FR (1) | FR2219149B1 (enExample) |
| GB (1) | GB1423096A (enExample) |
| IE (1) | IE38913B1 (enExample) |
| IT (1) | IT1008895B (enExample) |
| NL (1) | NL7402267A (enExample) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE48928C (de) * | FARBENFABRIKEN VORM. FRIEDR. BAYER & COin Elberfeld | Verfahren zur Darstellung von unsymmetrisch substituirten Diarnidotriphenylmethan-Derivaten und von Sulfosäuren derselben | ||
| FR456498A (fr) * | 1912-06-19 | 1913-08-27 | Leopold Cassella Et C G M B H | Procédé pour la production de colorants halogénés de la série des rosanilines |
| GB191413604A (en) * | 1914-06-04 | 1915-08-05 | Philip Arthur Newton | Manufacture and Production of New Dyes of the Triphenylmethane Series. |
| DE741008C (de) * | 1938-03-29 | 1943-11-02 | Ig Farbenindustrie Ag | Verfahren zur Herstellung von basischen Triarylmethanfarbstoffen |
| JPS419536Y1 (enExample) * | 1964-01-23 | 1966-05-09 | ||
| NL6911540A (enExample) * | 1969-07-28 | 1971-02-01 |
-
1973
- 1973-02-22 DE DE19732308724 patent/DE2308724C3/de not_active Expired
-
1974
- 1974-02-14 CA CA192,572A patent/CA1014173A/en not_active Expired
- 1974-02-19 NL NL7402267A patent/NL7402267A/xx unknown
- 1974-02-19 AU AU65760/74A patent/AU6576074A/en not_active Expired
- 1974-02-20 CH CH236574A patent/CH593908A5/xx not_active IP Right Cessation
- 1974-02-20 BR BR124574A patent/BR7401245D0/pt unknown
- 1974-02-20 IT IT4853974A patent/IT1008895B/it active
- 1974-02-21 ES ES423480A patent/ES423480A1/es not_active Expired
- 1974-02-21 IE IE34974A patent/IE38913B1/xx unknown
- 1974-02-21 BE BE141215A patent/BE811379A/xx unknown
- 1974-02-22 FR FR7406196A patent/FR2219149B1/fr not_active Expired
- 1974-02-22 GB GB822074A patent/GB1423096A/en not_active Expired
- 1974-02-22 JP JP2063974A patent/JPS49115195A/ja active Pending
Non-Patent Citations (1)
| Title |
|---|
| NICHTS ERMITTELT * |
Also Published As
| Publication number | Publication date |
|---|---|
| AU6576074A (en) | 1975-08-21 |
| BE811379A (fr) | 1974-08-21 |
| CA1014173A (en) | 1977-07-19 |
| NL7402267A (enExample) | 1974-08-26 |
| BR7401245D0 (pt) | 1974-11-05 |
| DE2308724B2 (de) | 1977-10-27 |
| JPS49115195A (enExample) | 1974-11-02 |
| CH593908A5 (enExample) | 1977-12-30 |
| IT1008895B (it) | 1976-11-30 |
| FR2219149B1 (enExample) | 1979-01-26 |
| DE2308724A1 (de) | 1974-09-12 |
| ES423480A1 (es) | 1976-05-16 |
| IE38913B1 (en) | 1978-06-21 |
| IE38913L (en) | 1974-08-22 |
| FR2219149A1 (enExample) | 1974-09-20 |
| GB1423096A (en) | 1976-01-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |