DE2022451A1 - Polyazofarbstoffe,ihre Herstellung und Verwendung - Google Patents
Polyazofarbstoffe,ihre Herstellung und VerwendungInfo
- Publication number
- DE2022451A1 DE2022451A1 DE19702022451 DE2022451A DE2022451A1 DE 2022451 A1 DE2022451 A1 DE 2022451A1 DE 19702022451 DE19702022451 DE 19702022451 DE 2022451 A DE2022451 A DE 2022451A DE 2022451 A1 DE2022451 A1 DE 2022451A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- amino
- polyazo dyes
- polyazo
- parts
- 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 41
- -1 Polyazo Polymers 0.000 title claims description 28
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 13
- 239000010985 leather Substances 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 9
- 238000004043 dyeing Methods 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 150000008049 diazo compounds Chemical class 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- RQCDKJFKYGNXBD-UHFFFAOYSA-N 4-(hydroxymethyl)benzene-1,3-diol Chemical compound OCC1=CC=C(O)C=C1O RQCDKJFKYGNXBD-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 3
- OPOOKGLABHKUCE-UHFFFAOYSA-N 2-(hydroxymethyl)benzene-1,3-diol Chemical compound OCC1=C(O)C=CC=C1O OPOOKGLABHKUCE-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- 244000061775 Olea africana Species 0.000 description 5
- 235000002852 Olea africana Nutrition 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 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 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 240000007817 Olea europaea Species 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000001049 brown dye Substances 0.000 description 2
- 244000309466 calf Species 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- LKTXPVRHGWOMSG-UHFFFAOYSA-N (2-aminophenyl)-phenylsulfamic acid Chemical compound NC1=CC=CC=C1N(S(O)(=O)=O)C1=CC=CC=C1 LKTXPVRHGWOMSG-UHFFFAOYSA-N 0.000 description 1
- JYYLQSCZISREGY-UHFFFAOYSA-N 2-amino-4-chlorobenzoic acid Chemical compound NC1=CC(Cl)=CC=C1C(O)=O JYYLQSCZISREGY-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- RUKISNQKOIKZGT-UHFFFAOYSA-N 2-nitrodiphenylamine Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=CC=C1 RUKISNQKOIKZGT-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 description 1
- HYKDWGUFDOYDGV-UHFFFAOYSA-N 4-anilinobenzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1NC1=CC=CC=C1 HYKDWGUFDOYDGV-UHFFFAOYSA-N 0.000 description 1
- UEALKTCRMBVTFN-UHFFFAOYSA-N 4-nitroanthranilic acid Chemical compound NC1=CC([N+]([O-])=O)=CC=C1C(O)=O UEALKTCRMBVTFN-UHFFFAOYSA-N 0.000 description 1
- 101000720704 Homo sapiens Neuronal migration protein doublecortin Proteins 0.000 description 1
- 102100025929 Neuronal migration protein doublecortin Human genes 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- 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
- D06P3/32—Material containing basic nitrogen containing amide groups leather skins
-
- 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/18—Trisazo or higher polyazo dyes
- C09B33/22—Trisazo dyes of the type A->B->K<-C
-
- 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
- D06P3/32—Material containing basic nitrogen containing amide groups leather skins
- D06P3/3206—Material containing basic nitrogen containing amide groups leather skins using acid dyes
- D06P3/3226—Material containing basic nitrogen containing amide groups leather skins using acid dyes dis-polyazo
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH728169A CH517147A (de) | 1969-05-13 | 1969-05-13 | Verfahren zur Herstellung von Polyazoverbindungen |
| CH1904369 | 1969-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2022451A1 true DE2022451A1 (de) | 1970-11-19 |
Family
ID=25701074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702022451 Pending DE2022451A1 (de) | 1969-05-13 | 1970-05-08 | Polyazofarbstoffe,ihre Herstellung und Verwendung |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3751407A (enExample) |
| JP (1) | JPS4817648B1 (enExample) |
| BE (1) | BE750197A (enExample) |
| CA (1) | CA972354A (enExample) |
| DE (1) | DE2022451A1 (enExample) |
| ES (1) | ES379536A1 (enExample) |
| FR (1) | FR2042605B1 (enExample) |
| GB (1) | GB1310825A (enExample) |
| HK (1) | HK50976A (enExample) |
| KE (1) | KE2649A (enExample) |
| NL (1) | NL7006452A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5285153U (enExample) * | 1975-12-23 | 1977-06-24 |
-
1970
- 1970-04-15 US US00028974A patent/US3751407A/en not_active Expired - Lifetime
- 1970-04-16 CA CA080,289A patent/CA972354A/en not_active Expired
- 1970-04-16 GB GB1821270A patent/GB1310825A/en not_active Expired
- 1970-05-01 NL NL7006452A patent/NL7006452A/xx unknown
- 1970-05-08 DE DE19702022451 patent/DE2022451A1/de active Pending
- 1970-05-08 BE BE750197D patent/BE750197A/xx unknown
- 1970-05-11 ES ES379536A patent/ES379536A1/es not_active Expired
- 1970-05-12 JP JP45039798A patent/JPS4817648B1/ja active Pending
- 1970-05-13 FR FR707017369A patent/FR2042605B1/fr not_active Expired
-
1976
- 1976-07-10 KE KE2649*UA patent/KE2649A/xx unknown
- 1976-08-12 HK HK509/76*UA patent/HK50976A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2042605A1 (enExample) | 1971-02-12 |
| ES379536A1 (es) | 1973-04-01 |
| KE2649A (en) | 1976-07-30 |
| BE750197A (fr) | 1970-10-16 |
| CA972354A (en) | 1975-08-05 |
| GB1310825A (en) | 1973-03-21 |
| FR2042605B1 (enExample) | 1974-07-12 |
| HK50976A (en) | 1976-08-20 |
| NL7006452A (enExample) | 1970-11-17 |
| JPS4817648B1 (enExample) | 1973-05-31 |
| US3751407A (en) | 1973-08-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2525418A1 (de) | Organische verbindungen, deren herstellung und verwendung | |
| DE2024047C3 (de) | Polyazofarbstoffe, ihre Metallkomplexverbindungen, ihre Herstellung und Verwendung | |
| DE3034686A1 (de) | Chromkomplexe von disazoverbindungen, deren herstellung und verwendung | |
| DE2022451A1 (de) | Polyazofarbstoffe,ihre Herstellung und Verwendung | |
| EP0016975B1 (de) | Polyazofarbstoffe sowie ihre Verwendung zum Färben von amino- und hydroxygruppenhaltigen Fasermaterialien und Leder | |
| DE1292277B (de) | Verfahren zur Herstellung von Polyazofarbstoffen | |
| DE2734806A1 (de) | Wasserloesliche trisazofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung | |
| DE2347551C3 (de) | Trisazoverbindungen, Verfahren zu deren Herstellung und ihre Verwendung zum Färben von Papier und Leder | |
| DE2346462A1 (de) | Wasserloesliche pentakis-azofarbstoffe | |
| DE2519657A1 (de) | Farbstoffzwischenprodukte und daraus herstellbare farbstoffe | |
| DE2500426C2 (de) | Wasserlösliche Trisazofarbstoffe und deren Verwendung | |
| DE2033602A1 (de) | Polyazofarbstoffe, ihre Herstellung und Verwendung | |
| DE2306768C2 (de) | Polyazoverbindungen, ihre Herstellung und Verwendung | |
| DE2110771C3 (de) | Trisazofarbstoffe und ihre Verwendung zum Färben hydroxylgruppenhaltiger und stickstoffhaltiger Fasermaterialien | |
| DE2408907C3 (de) | Wasserlösliche Tetrakisazofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung zum Färben von Leder | |
| EP0074510B1 (de) | Neue wasserlösliche Trisazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben von Leder und Pelz | |
| DE2058816C3 (de) | Wasserlöslicher Disazofarbstoff, Verfahren zu seiner Herstellung und seine Verwendung zum Färben von Leder und Pelz | |
| DE1769398B2 (de) | Wasserlösliche Phthalocyanin-Azofarbstoffe sowie Verfahren zu deren Herstellung und deren Verwendung | |
| DE2542410C2 (de) | Organische Verbindungen, deren Herstellung und Verwendung | |
| DE2201512A1 (de) | Neue,von Benzhydrol stammende Azofarbstoffe und Verfahren zu ihrer Herstellung | |
| DE2038473C3 (de) | Metallhaltige, sulfonsäuregruppenhaltige 2 zu 1 -Azokomplexfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE2159380C3 (de) | Polyazofarbstoffe und Verfahren zu deren Herstellung und Verwendung | |
| DE666146C (de) | Verfahren zur Herstellung von o-Oxyazofarbstoffen | |
| DE1927212C (de) | Wasserlösliche Diasazofarbstoffe | |
| DE2261397A1 (de) | Polyazoverbindungen, ihre herstellung und verwendung |