DE1282815B - Verfahren zur Herstellung wasserunloeslicher Monoazofarbstoffe - Google Patents
Verfahren zur Herstellung wasserunloeslicher MonoazofarbstoffeInfo
- Publication number
- DE1282815B DE1282815B DEC34750A DEC0034750A DE1282815B DE 1282815 B DE1282815 B DE 1282815B DE C34750 A DEC34750 A DE C34750A DE C0034750 A DEC0034750 A DE C0034750A DE 1282815 B DE1282815 B DE 1282815B
- Authority
- DE
- Germany
- Prior art keywords
- water
- general formula
- mole
- dyes
- solubilizing groups
- 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
- 239000000975 dye Substances 0.000 title claims description 15
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- -1 carbalkoxyalkyl Chemical group 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000000987 azo dye Substances 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxy-acetic acid Natural products OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 4
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 2
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 2
- YYLYBPJQUOYBQN-UHFFFAOYSA-N 2-chloro-4-phenylaniline Chemical group C1=C(Cl)C(N)=CC=C1C1=CC=CC=C1 YYLYBPJQUOYBQN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- IGSFOXNHUBLZHU-UHFFFAOYSA-N 2,4-dichloro-5-methylaniline Chemical compound CC1=CC(N)=C(Cl)C=C1Cl IGSFOXNHUBLZHU-UHFFFAOYSA-N 0.000 description 1
- PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001049 brown dye Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
- C09B43/20—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with monocarboxylic acids, carbamic acid esters or halides, mono- isocyanates or haloformic acid esters
- C09B43/202—Aliphatic, cycloaliphatic, araliphatic carboxylic acids
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
- C09B43/20—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with monocarboxylic acids, carbamic acid esters or halides, mono- isocyanates or haloformic acid esters
- C09B43/22—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with monocarboxylic acids, carbamic acid esters or halides, mono- isocyanates or haloformic acid esters having the carboxylic group directly attached to an aromatic carbocyclic ring
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04F—FINISHING WORK ON BUILDINGS, e.g. STAIRS, FLOORS
- E04F13/00—Coverings or linings, e.g. for walls or ceilings
- E04F13/002—Coverings or linings, e.g. for walls or ceilings made of webs, e.g. of fabrics, or wallpaper, used as coverings or linings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Civil Engineering (AREA)
- Structural Engineering (AREA)
- Coloring (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC34750A DE1282815B (de) | 1964-12-24 | 1964-12-24 | Verfahren zur Herstellung wasserunloeslicher Monoazofarbstoffe |
| US513828A US3592807A (en) | 1964-12-24 | 1965-12-14 | Water-insoluble (n-cyanoloweralkyl-n-acyloxyloweralkylamino)-phenylazo-benzene dyestuffs |
| NL656516268A NL147772B (nl) | 1964-12-24 | 1965-12-14 | Werkwijze ter bereiding van in water onoplosbare monoazokleurstoffen. |
| GB54340/65A GB1058378A (en) | 1964-12-24 | 1965-12-22 | Water-insoluble monoazo dyestuffs |
| FR43557A FR1461855A (fr) | 1964-12-24 | 1965-12-23 | Colorants mono-azoïques insolubles dans l'eau et leur préparation |
| CH1777565A CH454314A (de) | 1964-12-24 | 1965-12-23 | Verfahren zur Herstellung wasserunlöslicher Monoazofarbstoffe |
| BE674312D BE674312A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1964-12-24 | 1965-12-24 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC34750A DE1282815B (de) | 1964-12-24 | 1964-12-24 | Verfahren zur Herstellung wasserunloeslicher Monoazofarbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1282815B true DE1282815B (de) | 1968-11-14 |
Family
ID=7021476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC34750A Pending DE1282815B (de) | 1964-12-24 | 1964-12-24 | Verfahren zur Herstellung wasserunloeslicher Monoazofarbstoffe |
Country Status (7)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1544367B1 (de) * | 1965-01-15 | 1970-01-22 | Basf Ag | Wasserunloesliche p-Aminoazofarbstoffe |
| EP0047376A3 (en) * | 1980-08-14 | 1982-06-30 | Cassella Aktiengesellschaft | Mixture of monoazo disperse dyes, process for its preparation and process for dyeing and printing synthetic hydrophobic fibre material by the use of the mixture |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3971771A (en) * | 1970-11-11 | 1976-07-27 | Ciba-Geigy Ag | Monoazo compounds |
| US4119624A (en) * | 1972-06-08 | 1978-10-10 | Imperial Chemical Industries Limited | Disperse monoazo dyestuffs |
| DE2355076A1 (de) * | 1973-11-03 | 1975-05-07 | Bayer Ag | Kationische farbstoffe |
| DE2401246A1 (de) * | 1974-01-11 | 1975-07-24 | Bayer Ag | Kationische farbstoffe |
| CH606295A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-09-19 | 1978-10-31 | Sandoz Ag | |
| US4014864A (en) * | 1975-02-25 | 1977-03-29 | Ciba-Geigy Corporation | Heterocyclic substituted azo dyestuff |
| JPS51102565A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1975-03-07 | 1976-09-10 | Hitachi Ltd |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1069313B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1959-11-19 | |||
| FR1304317A (fr) * | 1961-10-21 | 1962-09-21 | Bayer Ag | Colorants azoïques, procédé pour leur préparation et leur application |
-
1964
- 1964-12-24 DE DEC34750A patent/DE1282815B/de active Pending
-
1965
- 1965-12-14 NL NL656516268A patent/NL147772B/xx unknown
- 1965-12-14 US US513828A patent/US3592807A/en not_active Expired - Lifetime
- 1965-12-22 GB GB54340/65A patent/GB1058378A/en not_active Expired
- 1965-12-23 CH CH1777565A patent/CH454314A/de unknown
- 1965-12-23 FR FR43557A patent/FR1461855A/fr not_active Expired
- 1965-12-24 BE BE674312D patent/BE674312A/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1069313B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1959-11-19 | |||
| FR1304317A (fr) * | 1961-10-21 | 1962-09-21 | Bayer Ag | Colorants azoïques, procédé pour leur préparation et leur application |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1544367B1 (de) * | 1965-01-15 | 1970-01-22 | Basf Ag | Wasserunloesliche p-Aminoazofarbstoffe |
| EP0047376A3 (en) * | 1980-08-14 | 1982-06-30 | Cassella Aktiengesellschaft | Mixture of monoazo disperse dyes, process for its preparation and process for dyeing and printing synthetic hydrophobic fibre material by the use of the mixture |
Also Published As
| Publication number | Publication date |
|---|---|
| CH454314A (de) | 1968-04-15 |
| BE674312A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-04-15 |
| US3592807A (en) | 1971-07-13 |
| GB1058378A (en) | 1967-02-08 |
| FR1461855A (fr) | 1966-12-09 |
| NL6516268A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-06-27 |
| NL147772B (nl) | 1975-11-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2340569C2 (de) | Azofarbstoffe | |
| DE1220061B (de) | Verfahren zur Herstellung von wasserunloeslichen Azofarbstoffen | |
| DE1282815B (de) | Verfahren zur Herstellung wasserunloeslicher Monoazofarbstoffe | |
| DE1213551B (de) | Verfahren zur Herstellung wasserunloeslicher Monoazofarbstoffe | |
| DE2630988C2 (de) | Azofarbstoffe | |
| DE2254017C2 (de) | Wasserunlösliche Azofarbstoffe und Verfahren zu ihrer Herstellung | |
| DE1940685C3 (de) | Dispersionsfarbstoffe der Amino pyrazolreihe, Verfahren zu ihrer Her Stellung und Verwendung | |
| DE918634C (de) | Verfahren zur Herstellung ueberfaerbeechter Faerbungen auf Acetylcellulose sowie linearen Polyamiden oder Polyurethanen | |
| DE1544530C3 (de) | Wasserunlösliche Alkenyl-Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE1153840B (de) | Verfahren zur Herstellung wasserunloeslicher Azofarbstoffe | |
| DE1644174A1 (de) | Wasserunloesliche Azofarbstoffe und Verfahren zu deren Herstellung und Verwendung | |
| DE2010491C3 (de) | In Wasser lösliche Azofarbstoffe und ihre Verwendung | |
| DE1221746B (de) | Verfahren zur Herstellung wasserunloeslicher Monoazofarbstoffe | |
| DE2130040B2 (de) | Wasserunlösliche Monoazoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE1644232C3 (de) | Wasserunlösliche Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE1283988B (de) | Verfahren zur Herstellung wasserunloeslicher Monoazofarbstoffe | |
| DE1224857B (de) | Verfahren zur Herstellung wasserunloeslicher Monoazofarbstoffe | |
| DE1544451C3 (de) | Wasserunlösliche Monoazofarbstoffe und Verfahren zu ihrer Herstellung | |
| DE1260654B (de) | Verfahren zur Herstellung von Monoazofarbstoffen | |
| DE1444642A1 (de) | Verfahren zur Herstellung wasserunloeslicher Monoazofarbstoffe | |
| DE2035644A1 (de) | Disazofarbstoffe | |
| DE1644122C3 (de) | Sulfonsäure- und carbonsäuregruppenfreie wasserunlösliche Monoazofarbstoffe und Verfahren zu ihrer Herstellung | |
| DE1276255B (de) | Verfahren zur Herstellung von wasserunloeslichen Monoazofarbstoffen | |
| DE633266C (de) | Verfahren zur Herstellung von o-Oxyazofarbstoffen | |
| DE2338089A1 (de) | Wasserunloesliche monoazofarbstoffe und verfahren zu ihrer herstellung |