DE1644388C3 - Wasserlösliche Dis- und Trisazofarbstoffe - Google Patents
Wasserlösliche Dis- und TrisazofarbstoffeInfo
- Publication number
- DE1644388C3 DE1644388C3 DE19671644388 DE1644388A DE1644388C3 DE 1644388 C3 DE1644388 C3 DE 1644388C3 DE 19671644388 DE19671644388 DE 19671644388 DE 1644388 A DE1644388 A DE 1644388A DE 1644388 C3 DE1644388 C3 DE 1644388C3
- Authority
- DE
- Germany
- Prior art keywords
- parts
- water
- solution
- acid
- pyrazolone
- 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
- 239000000975 dye Substances 0.000 title claims description 18
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinyl group Chemical group C1(O)=CC(O)=CC=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- -1 nitrophenylazo group Chemical group 0.000 description 7
- 239000010985 leather Substances 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 239000012954 diazonium Substances 0.000 description 5
- 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 5
- 239000011780 sodium chloride Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical group CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- AYNPIRVEWMUJDE-UHFFFAOYSA-N 2,5-dichlorohydroquinone Chemical compound OC1=CC(Cl)=C(O)C=C1Cl AYNPIRVEWMUJDE-UHFFFAOYSA-N 0.000 description 1
- URNUWVIPNDXJGL-UHFFFAOYSA-N 2-chloro-1-(6-methoxy-2,2,4-trimethyl-3,4-dihydroquinolin-1-yl)ethanone Chemical compound ClCC(=O)N1C(C)(C)CC(C)C2=CC(OC)=CC=C21 URNUWVIPNDXJGL-UHFFFAOYSA-N 0.000 description 1
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- SXTRBTYGLBKYHW-UHFFFAOYSA-N C(C=1C(O)=CC=CC1)(=O)O.C(C=1C(O)=CC=CC1)(=O)O.C(C=1C(O)=CC=CC1)(=O)O.C(C=1C(O)=CC=CC1)(=O)O Chemical compound C(C=1C(O)=CC=CC1)(=O)O.C(C=1C(O)=CC=CC1)(=O)O.C(C=1C(O)=CC=CC1)(=O)O.C(C=1C(O)=CC=CC1)(=O)O SXTRBTYGLBKYHW-UHFFFAOYSA-N 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical group ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 230000020176 deacylation Effects 0.000 description 1
- 238000005947 deacylation reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- BFVHBHKMLIBQNN-UHFFFAOYSA-N n-(2-chlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1Cl BFVHBHKMLIBQNN-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229950000244 sulfanilic acid Drugs 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/04—Disazo dyes characterised by the tetrazo component the tetrazo component being a benzene derivative
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR55854A FR1480372A (fr) | 1966-03-31 | 1966-03-31 | Nouveaux colorants azoïques solubles dans l'eau |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1644388A1 DE1644388A1 (de) | 1972-06-15 |
| DE1644388B2 DE1644388B2 (de) | 1973-09-13 |
| DE1644388C3 true DE1644388C3 (de) | 1974-05-02 |
Family
ID=8605216
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671644388 Expired DE1644388C3 (de) | 1966-03-31 | 1967-03-30 | Wasserlösliche Dis- und Trisazofarbstoffe |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE695006A (online.php) |
| CH (1) | CH466463A (online.php) |
| DE (1) | DE1644388C3 (online.php) |
| FR (1) | FR1480372A (online.php) |
| GB (1) | GB1180781A (online.php) |
| NL (1) | NL6704358A (online.php) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH671023A5 (online.php) * | 1987-02-10 | 1989-07-31 | Ciba Geigy Ag |
-
1966
- 1966-03-31 FR FR55854A patent/FR1480372A/fr not_active Expired
-
1967
- 1967-03-03 BE BE695006D patent/BE695006A/xx unknown
- 1967-03-23 NL NL6704358A patent/NL6704358A/xx unknown
- 1967-03-30 CH CH447867A patent/CH466463A/fr unknown
- 1967-03-30 DE DE19671644388 patent/DE1644388C3/de not_active Expired
- 1967-03-31 GB GB1470567A patent/GB1180781A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL6704358A (online.php) | 1967-10-02 |
| GB1180781A (en) | 1970-02-11 |
| DE1644388A1 (de) | 1972-06-15 |
| FR1480372A (fr) | 1967-05-12 |
| BE695006A (online.php) | 1967-09-04 |
| DE1644388B2 (de) | 1973-09-13 |
| CH466463A (fr) | 1968-12-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1225318B (de) | Verfahren zur Herstellung von Azofarbstoffen und deren Metallkomplexverbindungen | |
| DE1126542B (de) | Verfahren zur Herstellung metallhaltiger Azofarbstoffe | |
| DE1246906B (de) | Verfahren zur Herstellung von wasserloeslichen Mono- oder Disazofarbstoffen | |
| DE1644388B2 (de) | Wasserlösliche Dis und Tnsazofarb stoffe | |
| DE2355279A1 (de) | Auf der faser diazotierbare direktfarbstoffe | |
| DE2734806A1 (de) | Wasserloesliche trisazofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung | |
| DE479926C (de) | Verfahren zur Darstellung von Azofarbstoffen | |
| DE1644391B1 (de) | Trisazofarbstoffe | |
| DE1098642B (de) | Verfahren zur Herstellung von kationischen Farbstoffen | |
| DE515231C (de) | Verfahren zur Darstellung von Disazofarbstoffen | |
| DE469288C (de) | Verfahren zur Darstellung entwickelbarer Trisazofarbstoffe | |
| AT101007B (de) | Verfahren zur Herstellung von Azofarbstoffen. | |
| DE623838C (online.php) | ||
| DE945343C (de) | Verfahren zur Herstellung von Disazofarbstoffen | |
| DE1153839B (de) | Verfahren zur Herstellung methylolgruppenhaltiger Farbstoffe | |
| DE604578C (de) | Verfahren zur Darstellung von Azofarbstoffen | |
| DE717115C (de) | Verfahren zur Herstellung von Azofarbstoffen | |
| DE842090C (de) | Verfahren zur Herstellung von auf der Faser oder in Substanz chromierbaren Azofarbstoffen | |
| DE743849C (de) | Verfahren zur Herstellung von primaeren Disazofarbstoffen | |
| DE818670C (de) | Verfahren zur Herstellung von Trisazofarbstoffen | |
| DE842380C (de) | Verfahren zur Herstellung von Monoazofarbstoffen | |
| AT236002B (de) | Verfahren zur Herstellung von neuen reaktiven Monoazofarbstoffen | |
| DE1079756B (de) | Verfahren zur Herstellung wasserloeslicher methylolgruppenhaltiger Farbstoffe | |
| DE76816C (de) | Verfahren zur Darstellung von braunen Substantiven Farbstoffen der p-Phenylendiaminreihe aus p-Amidobenzolazosalicylsäure | |
| DE548393C (de) | Verfahren zur Darstellung von Monoazofarbstoffen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |