DE2262675A1 - Disazofarbstoffe - Google Patents
DisazofarbstoffeInfo
- Publication number
- DE2262675A1 DE2262675A1 DE19722262675 DE2262675A DE2262675A1 DE 2262675 A1 DE2262675 A1 DE 2262675A1 DE 19722262675 DE19722262675 DE 19722262675 DE 2262675 A DE2262675 A DE 2262675A DE 2262675 A1 DE2262675 A1 DE 2262675A1
- Authority
- DE
- Germany
- Prior art keywords
- hydroxynaphthalene
- sulfonic acid
- dyes
- coupling component
- amino
- 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 19
- LCZPIYCNOWJWPQ-UHFFFAOYSA-I disodium;chromium(3+);1-[(2-oxidonaphthalen-1-yl)diazenyl]-4-sulfonaphthalen-2-olate;3-oxido-4-[(2-oxidonaphthalen-1-yl)diazenyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].[Cr+3].C12=CC=CC=C2C(S(=O)(=O)O)=CC([O-])=C1N=NC1=C([O-])C=CC2=CC=CC=C12.C1=CC=C2C(N=NC3=C4C=CC=CC4=CC=C3[O-])=C([O-])C=C(S([O-])(=O)=O)C2=C1 LCZPIYCNOWJWPQ-UHFFFAOYSA-I 0.000 title 1
- 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
- 230000002378 acidificating effect Effects 0.000 claims description 9
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 claims description 7
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 6
- 238000004043 dyeing Methods 0.000 claims description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 5
- VKURVCNKVWKGLX-UHFFFAOYSA-N 5-amino-2-(4-aminoanilino)benzenesulfonic acid Chemical compound C1=CC(N)=CC=C1NC1=CC=C(N)C=C1S(O)(=O)=O VKURVCNKVWKGLX-UHFFFAOYSA-N 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 229920002994 synthetic fiber Polymers 0.000 claims description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 claims description 2
- 239000012209 synthetic fiber Substances 0.000 claims 2
- 150000005204 hydroxybenzenes Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 14
- 239000004952 Polyamide Substances 0.000 description 7
- 229920002647 polyamide Polymers 0.000 description 7
- 239000002253 acid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- KZQYIMCESJLPQH-UHFFFAOYSA-N Demethylated antipyrine Chemical compound N1C(C)=CC(=O)N1C1=CC=CC=C1 KZQYIMCESJLPQH-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000010979 ruby Substances 0.000 description 3
- 229910001750 ruby Inorganic materials 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 2
- FBYMBFPXCCVIRA-UHFFFAOYSA-N 4,6-dihydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(O)=CC=C21 FBYMBFPXCCVIRA-UHFFFAOYSA-N 0.000 description 2
- FMKMKBLHMONXJM-UHFFFAOYSA-N 5-methyl-2-phenylpyrazol-3-amine Chemical compound N1=C(C)C=C(N)N1C1=CC=CC=C1 FMKMKBLHMONXJM-UHFFFAOYSA-N 0.000 description 2
- VVPHSMHEYVOVLH-UHFFFAOYSA-N 6-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(O)=CC=C21 VVPHSMHEYVOVLH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AOJZHOSAFRXPQQ-UHFFFAOYSA-N N1=C(C)C=C(O)N1C1=CC=CC=C1Cl Chemical compound N1=C(C)C=C(O)N1C1=CC=CC=C1Cl AOJZHOSAFRXPQQ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 235000005811 Viola adunca Nutrition 0.000 description 2
- 240000009038 Viola odorata Species 0.000 description 2
- 235000013487 Viola odorata Nutrition 0.000 description 2
- 235000002254 Viola papilionacea Nutrition 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229950011260 betanaphthol Drugs 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- ALNWQAFPXMGLTJ-UHFFFAOYSA-N n-(7-hydroxynaphthalen-1-yl)acetamide Chemical compound C1=C(O)C=C2C(NC(=O)C)=CC=CC2=C1 ALNWQAFPXMGLTJ-UHFFFAOYSA-N 0.000 description 2
- CPANFUIQOQQIGG-UHFFFAOYSA-N n-(7-hydroxynaphthalen-1-yl)methanesulfonamide Chemical compound C1=C(O)C=C2C(NS(=O)(=O)C)=CC=CC2=C1 CPANFUIQOQQIGG-UHFFFAOYSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- HGWQOFDAUWCQDA-UHFFFAOYSA-N 4-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(O)=CC=C(S(O)(=O)=O)C2=C1 HGWQOFDAUWCQDA-UHFFFAOYSA-N 0.000 description 1
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
- YGNDWDUEMICDLW-UHFFFAOYSA-N 7-anilino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C=1C=C2C(O)=CC(S(O)(=O)=O)=CC2=CC=1NC1=CC=CC=C1 YGNDWDUEMICDLW-UHFFFAOYSA-N 0.000 description 1
- ZLHGMJOGMLVDFS-UHFFFAOYSA-N 7-benzamido-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C=1C=C2C(O)=CC(S(O)(=O)=O)=CC2=CC=1NC(=O)C1=CC=CC=C1 ZLHGMJOGMLVDFS-UHFFFAOYSA-N 0.000 description 1
- KVHHMYZBFBSVDI-UHFFFAOYSA-N 8-aminonaphthalen-2-ol Chemical compound C1=C(O)C=C2C(N)=CC=CC2=C1 KVHHMYZBFBSVDI-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- RQCYWGBUFRPHJH-UHFFFAOYSA-N N1=C(C)C=C(O)N1C1=CC=C(S(O)(=O)=O)C=C1 Chemical compound N1=C(C)C=C(O)N1C1=CC=C(S(O)(=O)=O)C=C1 RQCYWGBUFRPHJH-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 244000172533 Viola sororia Species 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 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
- -1 p-sulfophenyl Chemical group 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 210000002268 wool Anatomy 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
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/24—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of a diaryl amine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722262675 DE2262675A1 (de) | 1972-12-21 | 1972-12-21 | Disazofarbstoffe |
| NL7317325A NL7317325A (cs) | 1972-12-21 | 1973-12-18 | |
| JP14144273A JPS4987874A (cs) | 1972-12-21 | 1973-12-19 | |
| JP14144173A JPS4990328A (cs) | 1972-12-21 | 1973-12-19 | |
| CH1777773A CH567620B5 (cs) | 1972-12-21 | 1973-12-19 | |
| BR998073A BR7309980D0 (pt) | 1972-12-21 | 1973-12-19 | Processo para a preparacao de corantes disazo |
| BE139025A BE808820A (fr) | 1972-12-21 | 1973-12-19 | Colorants disazoiques |
| IT8368273A IT1001269B (it) | 1972-12-21 | 1973-12-19 | Coloranti disazoici |
| CH1777773D CH1777773A4 (cs) | 1972-12-21 | 1973-12-19 | |
| AR25160473A AR196961A1 (es) | 1972-12-21 | 1973-12-19 | Colorantes disazoicos |
| GB5910573A GB1404090A (en) | 1972-12-21 | 1973-12-20 | Disazo dyestuffs |
| ES421644A ES421644A1 (es) | 1972-12-21 | 1973-12-20 | Procedimiento para la produccion de colorantes disazoicos. |
| FR7346008A FR2211509B1 (cs) | 1972-12-21 | 1973-12-21 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722262675 DE2262675A1 (de) | 1972-12-21 | 1972-12-21 | Disazofarbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2262675A1 true DE2262675A1 (de) | 1974-06-27 |
Family
ID=5865096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722262675 Pending DE2262675A1 (de) | 1972-12-21 | 1972-12-21 | Disazofarbstoffe |
Country Status (11)
| Country | Link |
|---|---|
| JP (2) | JPS4990328A (cs) |
| AR (1) | AR196961A1 (cs) |
| BE (1) | BE808820A (cs) |
| BR (1) | BR7309980D0 (cs) |
| CH (2) | CH567620B5 (cs) |
| DE (1) | DE2262675A1 (cs) |
| ES (1) | ES421644A1 (cs) |
| FR (1) | FR2211509B1 (cs) |
| GB (1) | GB1404090A (cs) |
| IT (1) | IT1001269B (cs) |
| NL (1) | NL7317325A (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4341701A (en) | 1979-11-07 | 1982-07-27 | Ciba-Geigy Corporation | Production of pigments |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE58352C (de) * | leopold cassella & co. in Frankfurt a. M | Verfahren zur Darstellung von Farbstoffen aus Disazoverbindungen und Amidonaphtolsulfosäure. (2 | ||
| DE528891C (de) * | 1928-09-12 | 1931-07-04 | Ici Ltd | Verfahren zum Faerben von regenerierter Cellulose |
-
1972
- 1972-12-21 DE DE19722262675 patent/DE2262675A1/de active Pending
-
1973
- 1973-12-18 NL NL7317325A patent/NL7317325A/xx unknown
- 1973-12-19 IT IT8368273A patent/IT1001269B/it active
- 1973-12-19 CH CH1777773A patent/CH567620B5/xx not_active IP Right Cessation
- 1973-12-19 CH CH1777773D patent/CH1777773A4/xx unknown
- 1973-12-19 AR AR25160473A patent/AR196961A1/es active
- 1973-12-19 JP JP14144173A patent/JPS4990328A/ja active Pending
- 1973-12-19 JP JP14144273A patent/JPS4987874A/ja active Pending
- 1973-12-19 BE BE139025A patent/BE808820A/xx unknown
- 1973-12-19 BR BR998073A patent/BR7309980D0/pt unknown
- 1973-12-20 ES ES421644A patent/ES421644A1/es not_active Expired
- 1973-12-20 GB GB5910573A patent/GB1404090A/en not_active Expired
- 1973-12-21 FR FR7346008A patent/FR2211509B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE808820A (fr) | 1974-06-19 |
| FR2211509B1 (cs) | 1977-08-12 |
| NL7317325A (cs) | 1974-06-25 |
| JPS4990328A (cs) | 1974-08-29 |
| FR2211509A1 (cs) | 1974-07-19 |
| GB1404090A (en) | 1975-08-28 |
| CH1777773A4 (cs) | 1975-05-15 |
| BR7309980D0 (pt) | 1974-09-24 |
| CH567620B5 (cs) | 1975-10-15 |
| AR196961A1 (es) | 1974-02-28 |
| ES421644A1 (es) | 1976-03-16 |
| IT1001269B (it) | 1976-04-20 |
| JPS4987874A (cs) | 1974-08-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |