DE2421654C3 - Trisazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben und Bedrucken von Textilmaterialien - Google Patents
Trisazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben und Bedrucken von TextilmaterialienInfo
- Publication number
- DE2421654C3 DE2421654C3 DE2421654A DE2421654A DE2421654C3 DE 2421654 C3 DE2421654 C3 DE 2421654C3 DE 2421654 A DE2421654 A DE 2421654A DE 2421654 A DE2421654 A DE 2421654A DE 2421654 C3 DE2421654 C3 DE 2421654C3
- Authority
- DE
- Germany
- Prior art keywords
- sulfonic acid
- acid
- phenol
- sodium
- formula
- 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 34
- 238000004043 dyeing Methods 0.000 title description 7
- 238000000034 method Methods 0.000 title description 3
- 239000000463 material Substances 0.000 title description 2
- 239000004753 textile Substances 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 12
- 230000008878 coupling Effects 0.000 claims description 12
- 238000010168 coupling process Methods 0.000 claims description 12
- 238000005859 coupling reaction Methods 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 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
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 4
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims description 4
- 229940018564 m-phenylenediamine Drugs 0.000 claims description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 4
- IULJSGIJJZZUMF-UHFFFAOYSA-N 2-hydroxybenzenesulfonic acid Chemical compound OC1=CC=CC=C1S(O)(=O)=O IULJSGIJJZZUMF-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- 229940018563 3-aminophenol Drugs 0.000 claims description 2
- 229960001755 resorcinol Drugs 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000203 mixture Substances 0.000 description 15
- 239000004952 Polyamide Substances 0.000 description 14
- 229920002647 polyamide Polymers 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 5
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229910052979 sodium sulfide Inorganic materials 0.000 description 4
- 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 3
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 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
- UNBOSJFEZZJZLR-UHFFFAOYSA-N 4-(4-nitrophenylazo)aniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1 UNBOSJFEZZJZLR-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- -1 m-aminopbeno ! Chemical compound 0.000 description 2
- 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 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- XAQCYASNAMYTQA-UHFFFAOYSA-N 2,4-diamino-5-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=C(N)C=C1N XAQCYASNAMYTQA-UHFFFAOYSA-N 0.000 description 1
- 241000692783 Chylismia claviformis Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 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
- 150000001408 amides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- C09B35/35—Trisazo dyes in which the tetrazo component is a diamino-azo-aryl compound
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Color Printing (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2421654A DE2421654C3 (de) | 1974-05-04 | 1974-05-04 | Trisazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben und Bedrucken von Textilmaterialien |
| GB1610075A GB1459081A (en) | 1974-05-04 | 1975-04-18 | Trisazo dyestuffs |
| US05/571,865 US4009156A (en) | 1974-05-04 | 1975-04-25 | Hydroxynaphthalene trisazo dyestuffs |
| BE155944A BE828582A (fr) | 1974-05-04 | 1975-04-30 | Colorants trisazoiques, leur obtention et leur application |
| JP50052627A JPS50150730A (https=) | 1974-05-04 | 1975-05-02 | |
| ES437386A ES437386A1 (es) | 1974-05-04 | 1975-05-02 | Procedimiento para la obtencion colorantes trisazoicos. |
| FR7513844A FR2269565B1 (https=) | 1974-05-04 | 1975-05-02 | |
| IT22970/75A IT1037821B (it) | 1974-05-04 | 1975-05-02 | Coloranti tris azoici |
| BR3419/75D BR7502686A (pt) | 1974-05-04 | 1975-05-02 | Processo para a producao de corantes trisazo |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2421654A DE2421654C3 (de) | 1974-05-04 | 1974-05-04 | Trisazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben und Bedrucken von Textilmaterialien |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2421654A1 DE2421654A1 (de) | 1975-12-04 |
| DE2421654B2 DE2421654B2 (de) | 1980-02-07 |
| DE2421654C3 true DE2421654C3 (de) | 1980-10-02 |
Family
ID=5914671
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2421654A Expired DE2421654C3 (de) | 1974-05-04 | 1974-05-04 | Trisazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben und Bedrucken von Textilmaterialien |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4009156A (https=) |
| JP (1) | JPS50150730A (https=) |
| BE (1) | BE828582A (https=) |
| BR (1) | BR7502686A (https=) |
| DE (1) | DE2421654C3 (https=) |
| ES (1) | ES437386A1 (https=) |
| FR (1) | FR2269565B1 (https=) |
| GB (1) | GB1459081A (https=) |
| IT (1) | IT1037821B (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1095258B (it) * | 1978-04-28 | 1985-08-10 | Acna | Colorante disazoico e sua preparazione |
| DE3021979A1 (de) * | 1980-06-12 | 1981-12-17 | Bayer Ag, 5090 Leverkusen | Trisazo/azoxyfarbstoffgemische, verfahren zu ihrer herstellung sowie ihre verwendung |
| DE58909429D1 (de) * | 1988-07-22 | 1995-10-19 | Ciba Geigy Ag | Trisazofarbstoffe und Verfahren zum Färben von Papier. |
| JPH1046045A (ja) * | 1996-05-21 | 1998-02-17 | Ciba Specialty Chem Holding Inc | 三色染色又は三色捺染の方法 |
| KR20030016274A (ko) * | 2000-05-24 | 2003-02-26 | 클라리언트 파이넌스 (비브이아이)리미티드 | 유기 물질의 용도 |
| GB0226710D0 (en) * | 2002-11-15 | 2002-12-24 | Avecia Ltd | Inks |
| GB0226708D0 (en) * | 2002-11-15 | 2002-12-24 | Avecia Ltd | Compounds |
| JP7054657B2 (ja) * | 2018-07-24 | 2022-04-14 | 日本化薬株式会社 | アゾ化合物、インク組成物、記録方法及び着色体 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US536879A (en) * | 1895-04-02 | Gesellschaft fur anilin fabrikation | ||
| US615497A (en) * | 1898-12-06 | Christopher ris and charles simon | ||
| US536880A (en) * | 1895-04-02 | Gesellschaft fur anilin fabrikation | ||
| US536532A (en) * | 1895-03-26 | Gesellschaft fur anilin fabrikation | ||
| US658897A (en) * | 1900-07-20 | 1900-10-02 | Farbenfabriken Of Elberfeld Company | Blue trisazo dye. |
| US1209154A (en) * | 1916-07-24 | 1916-12-19 | Agfa Ag | Trisazo dyes. |
| US2203196A (en) * | 1936-06-17 | 1940-06-04 | Soc Of Chemical Ind | Polyazo dyestuffs and process of making same |
| FR956677A (https=) * | 1941-03-22 | 1950-02-02 | ||
| US2777839A (en) * | 1953-04-18 | 1957-01-15 | Bayer Ag | Grey trisazo dyestuffs |
| US3487067A (en) * | 1967-02-02 | 1969-12-30 | Kewanee Oil Co | Direct azo dyes for cellulose fibers |
-
1974
- 1974-05-04 DE DE2421654A patent/DE2421654C3/de not_active Expired
-
1975
- 1975-04-18 GB GB1610075A patent/GB1459081A/en not_active Expired
- 1975-04-25 US US05/571,865 patent/US4009156A/en not_active Expired - Lifetime
- 1975-04-30 BE BE155944A patent/BE828582A/xx unknown
- 1975-05-02 FR FR7513844A patent/FR2269565B1/fr not_active Expired
- 1975-05-02 BR BR3419/75D patent/BR7502686A/pt unknown
- 1975-05-02 ES ES437386A patent/ES437386A1/es not_active Expired
- 1975-05-02 IT IT22970/75A patent/IT1037821B/it active
- 1975-05-02 JP JP50052627A patent/JPS50150730A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ES437386A1 (es) | 1976-12-01 |
| DE2421654B2 (de) | 1980-02-07 |
| JPS50150730A (https=) | 1975-12-03 |
| IT1037821B (it) | 1979-11-20 |
| BR7502686A (pt) | 1976-03-16 |
| US4009156A (en) | 1977-02-22 |
| DE2421654A1 (de) | 1975-12-04 |
| GB1459081A (en) | 1976-12-22 |
| FR2269565A1 (https=) | 1975-11-28 |
| BE828582A (fr) | 1975-10-30 |
| FR2269565B1 (https=) | 1980-03-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |