CH620700A5 - Process for the preparation of 2-bromo-4'-nitro-6-chloro-4-(N,N-di(beta-methoxycarbonylethyl)amino)az obenzene having a novel crystal structure - Google Patents
Process for the preparation of 2-bromo-4'-nitro-6-chloro-4-(N,N-di(beta-methoxycarbonylethyl)amino)az obenzene having a novel crystal structure Download PDFInfo
- Publication number
- CH620700A5 CH620700A5 CH1102376A CH1102376A CH620700A5 CH 620700 A5 CH620700 A5 CH 620700A5 CH 1102376 A CH1102376 A CH 1102376A CH 1102376 A CH1102376 A CH 1102376A CH 620700 A5 CH620700 A5 CH 620700A5
- Authority
- CH
- Switzerland
- Prior art keywords
- bromo
- nitro
- methoxycarbonylethyl
- dye
- chloro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 239000013078 crystal Substances 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000007788 liquid Substances 0.000 claims description 16
- -1 azo compound Chemical class 0.000 claims description 14
- 238000002441 X-ray diffraction Methods 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002609 medium Substances 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 7
- 238000010586 diagram Methods 0.000 claims description 6
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 description 25
- 239000006185 dispersion Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- GLUCALKKMFBJEB-UHFFFAOYSA-N 2-bromo-6-chloro-4-nitroaniline Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Br GLUCALKKMFBJEB-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- NQMXUYSFHRWLLV-UHFFFAOYSA-N methyl 3-(n-(3-methoxy-3-oxopropyl)anilino)propanoate Chemical compound COC(=O)CCN(CCC(=O)OC)C1=CC=CC=C1 NQMXUYSFHRWLLV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- DQBNLFRFALCILS-UHFFFAOYSA-N 1-[(2-sulfonaphthalen-1-yl)methyl]naphthalene-2-sulfonic acid Chemical compound C1=CC=C2C(CC3=C4C=CC=CC4=CC=C3S(=O)(=O)O)=C(S(O)(=O)=O)C=CC2=C1 DQBNLFRFALCILS-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 1
- 229940066675 ricinoleate Drugs 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000011282 treatment 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0815—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)-
- C09B29/0816—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)- substituted by -COOR
- C09B29/0817—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)- substituted by -COOR having N(-aliphatic residue-COOR)2 as substituents
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0025—Crystal modifications; Special X-ray patterns
- C09B67/0028—Crystal modifications; Special X-ray patterns of azo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3594875A GB1543316A (en) | 1975-09-01 | 1975-09-01 | Stabilised disperse azo dyestuff |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH620700A5 true CH620700A5 (en) | 1980-12-15 |
Family
ID=10383284
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1102376A CH620700A5 (en) | 1975-09-01 | 1976-08-31 | Process for the preparation of 2-bromo-4'-nitro-6-chloro-4-(N,N-di(beta-methoxycarbonylethyl)amino)az obenzene having a novel crystal structure |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5229822A (nl) |
| AR (1) | AR210156A1 (nl) |
| BE (1) | BE845511A (nl) |
| BR (1) | BR7605768A (nl) |
| CH (1) | CH620700A5 (nl) |
| DE (1) | DE2639401C3 (nl) |
| ES (1) | ES451146A1 (nl) |
| FR (1) | FR2322175A1 (nl) |
| GB (1) | GB1543316A (nl) |
| IT (1) | IT1064973B (nl) |
| NL (1) | NL7609436A (nl) |
| TR (1) | TR19366A (nl) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2918567A1 (de) * | 1979-05-09 | 1980-11-20 | Hoechst Ag | Kondensate aus addukten von phosphiten und propen-2-olen und deren herstellung |
| DE2921210A1 (de) | 1979-05-25 | 1980-12-04 | Hoechst Ag | Faerbestabiler monoazofarbstoff, dessen herstellung und verwendung |
| DE2950588A1 (de) * | 1979-12-15 | 1981-06-19 | Hoechst Ag, 6230 Frankfurt | Faerbestabiler monoazofarbstoff, dessen herstellung und verwendung |
| JPS58225156A (ja) * | 1982-06-21 | 1983-12-27 | Gosei Senriyou Gijutsu Kenkyu Kumiai | モノアゾ染料及びその製法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2007382A (en) * | 1932-08-16 | 1935-07-09 | Celanese Corp | Production of dispersions |
| DE734846C (de) * | 1939-03-04 | 1943-05-10 | Ig Farbenindustrie Ag | Verfahren zur Herstellung von Azofarbstoffen |
| DE1619535A1 (de) * | 1967-07-19 | 1971-05-19 | Bayer Ag | Faerbestabile Dispersionsfarbstoffe |
| CH559767A5 (en) * | 1972-12-12 | 1975-03-14 | Sandoz Ag | Azo-dispersion dye in beta-modification and prodn. - by prepn. and conditioning at relatively low temp., for continuous dyeing |
| DE2336717A1 (de) * | 1973-07-19 | 1975-02-06 | Basf Ag | Dispersionsstabile modifikation eines dispersionsfarbstoffs |
-
1975
- 1975-09-01 GB GB3594875A patent/GB1543316A/en not_active Expired
-
1976
- 1976-08-25 NL NL7609436A patent/NL7609436A/nl not_active Application Discontinuation
- 1976-08-25 BE BE170071A patent/BE845511A/xx unknown
- 1976-08-26 IT IT2658076A patent/IT1064973B/it active
- 1976-08-30 AR AR26450876A patent/AR210156A1/es active
- 1976-08-31 BR BR7605768A patent/BR7605768A/pt unknown
- 1976-08-31 CH CH1102376A patent/CH620700A5/de not_active IP Right Cessation
- 1976-08-31 FR FR7626256A patent/FR2322175A1/fr active Pending
- 1976-09-01 TR TR1936676A patent/TR19366A/xx unknown
- 1976-09-01 JP JP10541476A patent/JPS5229822A/ja active Pending
- 1976-09-01 DE DE19762639401 patent/DE2639401C3/de not_active Expired
- 1976-09-01 ES ES451146A patent/ES451146A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES451146A1 (es) | 1977-08-16 |
| NL7609436A (nl) | 1977-03-03 |
| JPS5229822A (en) | 1977-03-07 |
| AR210156A1 (es) | 1977-06-30 |
| IT1064973B (it) | 1985-02-25 |
| FR2322175A1 (fr) | 1977-03-25 |
| TR19366A (tr) | 1979-01-22 |
| DE2639401B2 (de) | 1981-01-15 |
| DE2639401A1 (de) | 1977-04-21 |
| BE845511A (fr) | 1977-02-25 |
| BR7605768A (pt) | 1977-08-23 |
| GB1543316A (en) | 1979-04-04 |
| DE2639401C3 (de) | 1982-02-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |