CH500940A - Procédé de préparation de dérivés de la nitroparaphénylènediamine - Google Patents
Procédé de préparation de dérivés de la nitroparaphénylènediamineInfo
- Publication number
- CH500940A CH500940A CH722868A CH722868A CH500940A CH 500940 A CH500940 A CH 500940A CH 722868 A CH722868 A CH 722868A CH 722868 A CH722868 A CH 722868A CH 500940 A CH500940 A CH 500940A
- Authority
- CH
- Switzerland
- Prior art keywords
- benzene
- nitro
- radical
- analysis
- amino
- Prior art date
Links
- 238000004043 dyeing Methods 0.000 title description 2
- IOCXBXZBNOYTLQ-UHFFFAOYSA-N 3-nitrobenzene-1,2-diamine Chemical compound NC1=CC=CC([N+]([O-])=O)=C1N IOCXBXZBNOYTLQ-UHFFFAOYSA-N 0.000 title 1
- -1 hydroxy- Chemical class 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 239000007795 chemical reaction product Substances 0.000 claims abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 66
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 238000002844 melting Methods 0.000 claims description 10
- 230000008018 melting Effects 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 239000000155 melt Substances 0.000 claims description 8
- 238000001953 recrystallisation Methods 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 6
- 238000000354 decomposition reaction Methods 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000003512 tertiary amines Chemical group 0.000 claims description 3
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- BMJXMAAIWXBKBD-UHFFFAOYSA-N aniline;dihydrochloride Chemical compound Cl.Cl.NC1=CC=CC=C1 BMJXMAAIWXBKBD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- ZPHQBFRCXUIIAZ-UHFFFAOYSA-N benzene;hydrochloride Chemical compound Cl.C1=CC=CC=C1 ZPHQBFRCXUIIAZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 239000012141 concentrate Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 239000000047 product Substances 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 abstract 1
- 239000000118 hair dye Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- QUMQBQADXFETJW-UHFFFAOYSA-N n-(4-chloro-3-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(Cl)C([N+]([O-])=O)=C1 QUMQBQADXFETJW-UHFFFAOYSA-N 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- FOHHWGVAOVDVLP-UHFFFAOYSA-N 4-chloro-3-nitroaniline Chemical compound NC1=CC=C(Cl)C([N+]([O-])=O)=C1 FOHHWGVAOVDVLP-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- 102000011782 Keratins Human genes 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- VQCONEHUJAOBIK-UHFFFAOYSA-N diethyl(methyl)azanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CC[NH+](C)CC.CC[NH+](C)CC VQCONEHUJAOBIK-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- KFTYNYHJHKCRKU-UHFFFAOYSA-N n-(3-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC([N+]([O-])=O)=C1 KFTYNYHJHKCRKU-UHFFFAOYSA-N 0.000 description 1
- ZTQDYDIRBKMMQB-UHFFFAOYSA-N n-(4-aminophenyl)nitramide Chemical class NC1=CC=C(N[N+]([O-])=O)C=C1 ZTQDYDIRBKMMQB-UHFFFAOYSA-N 0.000 description 1
- OAEWODJOQXHPGS-UHFFFAOYSA-N n-(4-chloro-3-nitrophenyl)benzenesulfonamide Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(NS(=O)(=O)C=2C=CC=CC=2)=C1 OAEWODJOQXHPGS-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/418—Amines containing nitro groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
- A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
-
- 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
- C09B51/00—Nitro or nitroso dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/08—Material containing basic nitrogen containing amide groups using oxidation dyes
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH159470A CH503497A (fr) | 1967-05-16 | 1968-05-16 | Composition tinctoriale contenant de nouveaux dérivés de la nitroparaphénylènediamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU53676A LU53676A1 (forum.php) | 1967-05-16 | 1967-05-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH500940A true CH500940A (fr) | 1970-12-31 |
Family
ID=19725218
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH722868A CH500940A (fr) | 1967-05-16 | 1968-05-16 | Procédé de préparation de dérivés de la nitroparaphénylènediamine |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE715165A (forum.php) |
| CH (1) | CH500940A (forum.php) |
| DE (1) | DE1768464A1 (forum.php) |
| FR (1) | FR1575821A (forum.php) |
| GB (1) | GB1191976A (forum.php) |
| LU (1) | LU53676A1 (forum.php) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2571364B1 (fr) * | 1984-10-09 | 1987-07-17 | Oreal | Nouveau procede de preparation de nitroparaphenylenediamines n,n'-disubstituees, nouvelles oxazolidones utilisees dans ce procede, nouvelles nitroparaphenylenediamines n,n'-disubstituees obtenues selon ce procede et compositions tinctoriales contenant les nitroparaphenylenediamines n,n'-disubstituees obtenues selon ledit procede |
| DE4206536A1 (de) * | 1992-03-02 | 1993-09-09 | Henkel Kgaa | Direktziehende farbstoffe fuer fasern natuerlichen ursprungs und synthetische fasern |
-
1967
- 1967-05-16 LU LU53676A patent/LU53676A1/xx unknown
-
1968
- 1968-05-15 BE BE715165D patent/BE715165A/xx unknown
- 1968-05-16 FR FR1575821D patent/FR1575821A/fr not_active Expired
- 1968-05-16 GB GB2345968A patent/GB1191976A/en not_active Expired
- 1968-05-16 DE DE19681768464 patent/DE1768464A1/de not_active Ceased
- 1968-05-16 CH CH722868A patent/CH500940A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE1768464A1 (de) | 1971-08-12 |
| FR1575821A (forum.php) | 1969-07-25 |
| LU53676A1 (forum.php) | 1968-11-29 |
| GB1191976A (en) | 1970-05-13 |
| BE715165A (forum.php) | 1968-11-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1191849A (fr) | Composes utilisables pour la teinture des cheveux, leur procede de preparation, composition de teinture les contenant et procede de teinture de cheveux correspondant | |
| JPS6234752B2 (forum.php) | ||
| CH622699A5 (forum.php) | ||
| EP0331144B1 (fr) | Para-aminophénols 3-substitués, leur procédé de préparation, leur utilisation pour la teinture des fibres kératiniques et les composés intermédiaires utilisés dans le procédé de préparation | |
| CH661723A5 (fr) | Metaaminophenols substitues, leur procede de preparation, compositions tinctoriales pour cheveux les contenant et procede de teinture de cheveux correspondant. | |
| CH457484A (fr) | Procédé de préparation de nouveaux colorants nitrés | |
| EP0359618B1 (fr) | Para-aminophénols 2-substitués et leur utilisation pour la teinture des fibres kératiniques | |
| FR2567519A1 (fr) | Nouvelles isoindolinyl-alcoyl-piperazines, compositions pharmaceutiques les contenant, et leur procede de preparation | |
| LU83686A1 (fr) | Composition tinctoriale pour fibres keratiniques a base de colorants nitres benzeniques | |
| CA1220487A (fr) | Derives dimethyles de nitro-3 amino-4 aniline, leur procede de preparation et leur utilisation en teinture des fibres keratiniques | |
| FR2571364A1 (fr) | Nouveau procede de preparation de nitroparaphenylenediamines n,n'-disubstituees, nouvelles oxazolidones utilisees dans ce procede, nouvelles nitroparaphenylenediamines n,n'-disubstituees obtenues selon ce procede et compositions tinctoriales contenant les nitroparaphenylenediamines n,n'-disubstituees obtenues selon ledit procede | |
| CH616840A5 (en) | Dyeing composition for human hair | |
| FR2629454A1 (fr) | Procede de preparation de 1-methoxy-2,4-diamino-benzene, de certains de leurs composes et des produits intermediaires, ainsi que des teintures en solution aqueuse pour des fibres de keratine | |
| EP0002978B1 (fr) | Dérivés de thiazolidinedione-2,4, leur préparation et leur application en thérapeutique | |
| CH500940A (fr) | Procédé de préparation de dérivés de la nitroparaphénylènediamine | |
| EP0358550A2 (fr) | Procédé de préparation d'alfa, omega-diamines aliphatiques, composés nouveaux et leur utilisation en teinture capillaire | |
| CH653252A5 (fr) | Composition tinctoriale pour fibres keratiniques a base de nitroanilines, nitro-anilines et leur procede de preparation. | |
| CH394247A (fr) | Procédé de préparation de nouveaux aminoesters | |
| FR2647443A1 (forum.php) | ||
| CH658245A5 (fr) | Procede de preparation de nitro-anilines, compositions tinctoriales pour cheveux les contenant et nitro-anilines nouvelles. | |
| US3119867A (en) | Amino, nitro-phenyl-biguanides and amino, nitro-phenyl; guanyl-ureas | |
| BE895697A (fr) | Nouveaux composes utilisables pour la teinture des cheveux, leur procede de preparation, composition de teinture les contenant | |
| CH587795A5 (en) | 2-Aminoalkyl amino indanes - anti-arrhythmic,orally active, long-acting, not myocardial depressant | |
| CH627157A5 (forum.php) | ||
| FR2769910A1 (fr) | Procede de synthese de 2-hydroxyalkyl paraphenylenediamines, nouvelles 2-hydroxyalkyl paraphenylenediamines, leur utilisation pour la teinture d'oxydation, compositions tinctoriales et procedes de teinture |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |