DE2429673C3 - Verfahren zur Herstellung von symmetrischen 4-Halogen-4', 4''-diarylamino-triphenylmethanverbindungen und deren Verwendung zum Spinnfärben von Polyacrylnitril - Google Patents
Verfahren zur Herstellung von symmetrischen 4-Halogen-4', 4''-diarylamino-triphenylmethanverbindungen und deren Verwendung zum Spinnfärben von PolyacrylnitrilInfo
- Publication number
- DE2429673C3 DE2429673C3 DE2429673A DE2429673A DE2429673C3 DE 2429673 C3 DE2429673 C3 DE 2429673C3 DE 2429673 A DE2429673 A DE 2429673A DE 2429673 A DE2429673 A DE 2429673A DE 2429673 C3 DE2429673 C3 DE 2429673C3
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- aniline
- naphthylamine
- cyano
- trifluoromethyl
- 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 24
- 229920002239 polyacrylonitrile Polymers 0.000 title claims description 8
- 238000004043 dyeing Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 18
- -1 hydroxy, Phenylamino Chemical group 0.000 claims description 16
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 10
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 150000004982 aromatic amines Chemical class 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 229910015900 BF3 Inorganic materials 0.000 claims description 5
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 150000005171 halobenzenes Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 239000008346 aqueous phase Substances 0.000 claims description 3
- PDWJCROIGIXLPN-UHFFFAOYSA-N ethyl N-methoxysulfamate Chemical group CONS(=O)(=O)OCC PDWJCROIGIXLPN-UHFFFAOYSA-N 0.000 claims description 3
- 150000005002 naphthylamines Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 239000012074 organic phase Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical group ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000000975 dye Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 238000009987 spinning Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000002657 fibrous material Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000002166 wet spinning Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000012084 conversion product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000000578 dry spinning Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- BZVJOYBTLHNRDW-UHFFFAOYSA-N triphenylmethanamine Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)(N)C1=CC=CC=C1 BZVJOYBTLHNRDW-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 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
- C09B11/20—Preparation from other triarylmethane derivatives, e.g. by substitution, by replacement of substituents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2429673A DE2429673C3 (de) | 1974-06-20 | 1974-06-20 | Verfahren zur Herstellung von symmetrischen 4-Halogen-4', 4''-diarylamino-triphenylmethanverbindungen und deren Verwendung zum Spinnfärben von Polyacrylnitril |
| CH786375A CH627769A5 (de) | 1974-06-20 | 1975-06-17 | Verfahren zur herstellung von symmetrischen 4-halogen-4',4''-diarylamino-triphenylmethanverbindungen. |
| US05/587,413 US4041054A (en) | 1974-06-20 | 1975-06-17 | Process for the preparation of symmetric 4-halogen-4',4"-diarylamino-triphenylmethane compounds |
| JP50073243A JPS595146B2 (ja) | 1974-06-20 | 1975-06-18 | 対称性４−ハロゲン−及び（４及び２−ハロゲン）−４′，４″−ジフェニルアミノ−トリフェニルメタン化合物の製造法 |
| IT24525/75A IT1039103B (it) | 1974-06-20 | 1975-06-18 | Processo per la preparazione di composti 4 alogeno 4.4 diarilamino trifenilmetaici simmetrici |
| FR7519193A FR2275532A1 (fr) | 1974-06-20 | 1975-06-19 | Procede de preparation de composes de 4-halo-4', 4'' - diarylamino - triphenyl-methanes symetriques |
| GB26421/75A GB1502839A (en) | 1974-06-20 | 1975-06-20 | Process for the preparation of 2 - halogen- or 4-halogen - 4',4'' - diarylamino - triphenylmethane compounds |
| BE157543A BE830481A (fr) | 1974-06-20 | 1975-06-20 | Procede de preparation de composes de 4-halo-4',4"-diarylamino-triphenyl-methanes symetriques |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2429673A DE2429673C3 (de) | 1974-06-20 | 1974-06-20 | Verfahren zur Herstellung von symmetrischen 4-Halogen-4', 4''-diarylamino-triphenylmethanverbindungen und deren Verwendung zum Spinnfärben von Polyacrylnitril |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2429673A1 DE2429673A1 (de) | 1976-02-26 |
| DE2429673B2 DE2429673B2 (de) | 1980-08-21 |
| DE2429673C3 true DE2429673C3 (de) | 1981-04-16 |
Family
ID=5918530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2429673A Expired DE2429673C3 (de) | 1974-06-20 | 1974-06-20 | Verfahren zur Herstellung von symmetrischen 4-Halogen-4', 4''-diarylamino-triphenylmethanverbindungen und deren Verwendung zum Spinnfärben von Polyacrylnitril |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4041054A (esLanguage) |
| JP (1) | JPS595146B2 (esLanguage) |
| BE (1) | BE830481A (esLanguage) |
| CH (1) | CH627769A5 (esLanguage) |
| DE (1) | DE2429673C3 (esLanguage) |
| FR (1) | FR2275532A1 (esLanguage) |
| GB (1) | GB1502839A (esLanguage) |
| IT (1) | IT1039103B (esLanguage) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2259305B (en) * | 1991-09-05 | 1995-11-15 | Sandoz Ltd | 2:1 aluminium complexes |
| US5593491A (en) * | 1994-12-22 | 1997-01-14 | Basf Corporation | Method of preparing triarylmethane dyes and pigments |
| JP6463624B2 (ja) * | 2014-12-08 | 2019-02-06 | 東友ファインケム株式会社Ｄｏｎｇｗｏｏ Ｆｉｎｅ−Ｃｈｅｍ Ｃｏ．， Ｌｔｄ． | 化合物 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3112326A (en) * | 1959-06-19 | 1963-11-26 | Grace W R & Co | Polyarylmethane hydrazinium compounds |
| NL277914A (esLanguage) * | 1961-05-03 |
-
1974
- 1974-06-20 DE DE2429673A patent/DE2429673C3/de not_active Expired
-
1975
- 1975-06-17 US US05/587,413 patent/US4041054A/en not_active Expired - Lifetime
- 1975-06-17 CH CH786375A patent/CH627769A5/de not_active IP Right Cessation
- 1975-06-18 JP JP50073243A patent/JPS595146B2/ja not_active Expired
- 1975-06-18 IT IT24525/75A patent/IT1039103B/it active
- 1975-06-19 FR FR7519193A patent/FR2275532A1/fr active Granted
- 1975-06-20 BE BE157543A patent/BE830481A/xx unknown
- 1975-06-20 GB GB26421/75A patent/GB1502839A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US4041054A (en) | 1977-08-09 |
| GB1502839A (en) | 1978-03-01 |
| DE2429673B2 (de) | 1980-08-21 |
| FR2275532B1 (esLanguage) | 1980-06-27 |
| BE830481A (fr) | 1975-12-22 |
| CH627769A5 (de) | 1982-01-29 |
| FR2275532A1 (fr) | 1976-01-16 |
| JPS595146B2 (ja) | 1984-02-02 |
| JPS5113833A (en) | 1976-02-03 |
| IT1039103B (it) | 1979-12-10 |
| DE2429673A1 (de) | 1976-02-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |