DE2803992A1 - Wasserunloesliche monoazofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung - Google Patents
Wasserunloesliche monoazofarbstoffe, verfahren zu ihrer herstellung und ihre verwendungInfo
- Publication number
- DE2803992A1 DE2803992A1 DE19782803992 DE2803992A DE2803992A1 DE 2803992 A1 DE2803992 A1 DE 2803992A1 DE 19782803992 DE19782803992 DE 19782803992 DE 2803992 A DE2803992 A DE 2803992A DE 2803992 A1 DE2803992 A1 DE 2803992A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- carbon atoms
- formula
- alkyl
- aniline
- 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.)
- Withdrawn
Links
- 239000000975 dye Substances 0.000 title claims description 32
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical compound [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 description 12
- 238000004519 manufacturing process Methods 0.000 title description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 230000008878 coupling Effects 0.000 claims description 16
- 238000010168 coupling process Methods 0.000 claims description 16
- 238000005859 coupling reaction Methods 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 11
- 239000000049 pigment Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical class C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 claims description 4
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 claims description 4
- 238000004040 coloring Methods 0.000 claims description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000000976 ink Substances 0.000 claims description 4
- 150000002790 naphthalenes Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000002320 enamel (paints) Substances 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 239000003973 paint Substances 0.000 claims 1
- -1 4-methoxybenzamido Chemical group 0.000 description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- SVZQSGDHCHQFEE-UHFFFAOYSA-N n-(3-amino-4-methoxyphenyl)benzamide Chemical compound C1=C(N)C(OC)=CC=C1NC(=O)C1=CC=CC=C1 SVZQSGDHCHQFEE-UHFFFAOYSA-N 0.000 description 6
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 5
- 238000006193 diazotization reaction Methods 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000004922 lacquer Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910010413 TiO 2 Inorganic materials 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- UPBIVMVNDOALIE-UHFFFAOYSA-N n-(3-amino-2-methylphenyl)benzamide Chemical compound CC1=C(N)C=CC=C1NC(=O)C1=CC=CC=C1 UPBIVMVNDOALIE-UHFFFAOYSA-N 0.000 description 3
- IRFCTHNJIWUUJZ-UHFFFAOYSA-N n-(3-aminophenyl)benzamide Chemical compound NC1=CC=CC(NC(=O)C=2C=CC=CC=2)=C1 IRFCTHNJIWUUJZ-UHFFFAOYSA-N 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004640 Melamine resin Substances 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 125000005116 aryl carbamoyl group Chemical group 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- HCXZVGVPPSVNQB-UHFFFAOYSA-N n-(3-amino-4-methylphenyl)-2,4-dichlorobenzamide Chemical compound C1=C(N)C(C)=CC=C1NC(=O)C1=CC=C(Cl)C=C1Cl HCXZVGVPPSVNQB-UHFFFAOYSA-N 0.000 description 2
- ZKMYHZKZDMIROQ-UHFFFAOYSA-N n-(3-amino-4-methylphenyl)benzamide Chemical compound C1=C(N)C(C)=CC=C1NC(=O)C1=CC=CC=C1 ZKMYHZKZDMIROQ-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229910052573 porcelain Inorganic materials 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- WQHNWJBSROXROL-UHFFFAOYSA-N 1-chloro-3,5-dimethoxybenzene Chemical compound COC1=CC(Cl)=CC(OC)=C1 WQHNWJBSROXROL-UHFFFAOYSA-N 0.000 description 1
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- RUFOHZDEBFYQSV-UHFFFAOYSA-N 4-methoxy-3-nitroaniline Chemical compound COC1=CC=C(N)C=C1[N+]([O-])=O RUFOHZDEBFYQSV-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- SGYBFMHFBBYSFQ-UHFFFAOYSA-N C1(=CC=CC=C1)N1N=C(C=C1O)C(N)=O Chemical compound C1(=CC=CC=C1)N1N=C(C=C1O)C(N)=O SGYBFMHFBBYSFQ-UHFFFAOYSA-N 0.000 description 1
- BFCZBMZMVYRCAB-UHFFFAOYSA-N C1(=CC=CC=C1)N1N=C(C=C1O)C(NC1=C(C=CC(=C1)Cl)OC)=O Chemical compound C1(=CC=CC=C1)N1N=C(C=C1O)C(NC1=C(C=CC(=C1)Cl)OC)=O BFCZBMZMVYRCAB-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- DDKMFOUTRRODRE-UHFFFAOYSA-N chloromethanone Chemical compound Cl[C]=O DDKMFOUTRRODRE-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000009500 colour coating Methods 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229920001577 copolymer Chemical group 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007970 homogeneous dispersion Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- BSVOTWLTVAXQCV-UHFFFAOYSA-N n-(3-amino-4-methoxyphenyl)-2,4-dichlorobenzamide Chemical compound C1=C(N)C(OC)=CC=C1NC(=O)C1=CC=C(Cl)C=C1Cl BSVOTWLTVAXQCV-UHFFFAOYSA-N 0.000 description 1
- RTDMONGQVSSBBQ-UHFFFAOYSA-N n-(3-amino-4-methoxyphenyl)-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=C(OC)C(N)=C1 RTDMONGQVSSBBQ-UHFFFAOYSA-N 0.000 description 1
- ZKVYZULRTAMIQV-UHFFFAOYSA-N n-(3-amino-4-methylphenyl)-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC1=CC=C(C)C(N)=C1 ZKVYZULRTAMIQV-UHFFFAOYSA-N 0.000 description 1
- VPCSYWFYYDVQIP-UHFFFAOYSA-N n-(4-methoxy-3-nitrophenyl)benzamide Chemical compound C1=C([N+]([O-])=O)C(OC)=CC=C1NC(=O)C1=CC=CC=C1 VPCSYWFYYDVQIP-UHFFFAOYSA-N 0.000 description 1
- NSNPSJGHTQIXDO-UHFFFAOYSA-N naphthalene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CC=CC2=C1 NSNPSJGHTQIXDO-UHFFFAOYSA-N 0.000 description 1
- XNLBCXGRQWUJLU-UHFFFAOYSA-N naphthalene-2-carbonyl chloride Chemical compound C1=CC=CC2=CC(C(=O)Cl)=CC=C21 XNLBCXGRQWUJLU-UHFFFAOYSA-N 0.000 description 1
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical class N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000001238 wet grinding 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
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
-
- 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
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Paints Or Removers (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1984877A IT1076855B (it) | 1977-02-01 | 1977-02-01 | Coloranti monoazoici insolubili in acqua |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2803992A1 true DE2803992A1 (de) | 1978-08-03 |
Family
ID=11161777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782803992 Withdrawn DE2803992A1 (de) | 1977-02-01 | 1978-01-31 | Wasserunloesliche monoazofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS53114837A (en, 2012) |
| DE (1) | DE2803992A1 (en, 2012) |
| FR (1) | FR2378826A1 (en, 2012) |
| GB (1) | GB1596565A (en, 2012) |
| IT (1) | IT1076855B (en, 2012) |
| NL (1) | NL7800995A (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2587981B2 (ja) * | 1988-03-22 | 1997-03-05 | 三菱電線工業株式会社 | 耐熱老化性樹脂組成物 |
| AU2012228300C1 (en) | 2011-03-15 | 2015-03-05 | Novartis Ag | Inhaler |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH114916A (de) * | 1924-03-29 | 1926-05-17 | Hoechst Ag | Verfahren zur Darstellung eines Azofarbstoffes. |
| CH111495A (de) * | 1924-05-22 | 1925-08-17 | Chem Fab Rohner A G Pratteln | Verfahren zur Darstellung eines Monoazofarbstoffes. |
| US1872033A (en) * | 1931-02-02 | 1932-08-16 | Dow Chemical Co | Fast azo dye |
| FR810699A (fr) * | 1935-09-21 | 1937-03-26 | Ig Farbenindustrie Ag | Colorants mono-azoïques insolubles dans l'eau et procédé de préparation de ces colorants |
| FR850220A (fr) * | 1938-02-11 | 1939-12-11 | Ig Farbenindustrie Ag | Colorants mono-azoïques et procédé de préparation de ces colorants |
| FR50607E (fr) * | 1939-05-05 | 1941-01-27 | Ig Farbenindustrie Ag | Colorants monoazoïques et procédé de préparation de ces colorants |
| BE788450A (fr) * | 1971-09-08 | 1973-03-06 | Bayer Ag | Nouveaux pigments monoazoiques, leur procede de preparation et leurs applications |
-
1977
- 1977-02-01 IT IT1984877A patent/IT1076855B/it active
-
1978
- 1978-01-27 NL NL7800995A patent/NL7800995A/xx not_active Application Discontinuation
- 1978-01-30 FR FR7802477A patent/FR2378826A1/fr active Granted
- 1978-01-31 DE DE19782803992 patent/DE2803992A1/de not_active Withdrawn
- 1978-01-31 GB GB388678A patent/GB1596565A/en not_active Expired
- 1978-02-01 JP JP937278A patent/JPS53114837A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2378826A1 (fr) | 1978-08-25 |
| IT1076855B (it) | 1985-04-27 |
| GB1596565A (en) | 1981-08-26 |
| NL7800995A (nl) | 1978-08-03 |
| FR2378826B1 (en, 2012) | 1980-05-16 |
| JPS53114837A (en) | 1978-10-06 |
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