CA1064022A - Water-soluble disazo dyestuffs, a process for their preparation and their use for dyeing synthetic and natural polyamides - Google Patents
Water-soluble disazo dyestuffs, a process for their preparation and their use for dyeing synthetic and natural polyamidesInfo
- Publication number
- CA1064022A CA1064022A CA242,133A CA242133A CA1064022A CA 1064022 A CA1064022 A CA 1064022A CA 242133 A CA242133 A CA 242133A CA 1064022 A CA1064022 A CA 1064022A
- Authority
- CA
- Canada
- Prior art keywords
- parts
- water
- dyestuff
- good
- acid
- 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
- 239000004952 Polyamide Substances 0.000 title claims abstract description 9
- 229920002647 polyamide Polymers 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims description 5
- 230000008569 process Effects 0.000 title claims description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 3
- 238000004043 dyeing Methods 0.000 title abstract description 12
- 238000002360 preparation method Methods 0.000 title description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 5
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 2
- 239000000975 dye Substances 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 239000004744 fabric Substances 0.000 claims description 5
- 238000010025 steaming Methods 0.000 claims description 3
- 239000002562 thickening agent Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 5
- 150000003254 radicals Chemical class 0.000 abstract description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical group ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- 229940061334 2-phenylphenol Drugs 0.000 description 1
- 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 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 240000008886 Ceratonia siliqua Species 0.000 description 1
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000252233 Cyprinus carpio Species 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 244000228957 Ferula foetida Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VAYOSLLFUXYJDT-RDTXWAMCSA-N Lysergic acid diethylamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N(CC)CC)C2)=C3C2=CNC3=C1 VAYOSLLFUXYJDT-RDTXWAMCSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010026 decatizing Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 229940117927 ethylene oxide Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- -1 for 0xample Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 238000005406 washing Methods 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
- D06P3/06—Material containing basic nitrogen containing amide groups using acid dyes
-
- 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
- C09B31/062—Phenols
- C09B31/065—Phenols containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/28—Preparation of azo dyes from other azo compounds by etherification of hydroxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742460467 DE2460467A1 (de) | 1974-12-20 | 1974-12-20 | Wasserloesliche disazofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung zum faerben von synthetischen und natuerlichen polyamiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1064022A true CA1064022A (en) | 1979-10-09 |
Family
ID=5934047
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA242,133A Expired CA1064022A (en) | 1974-12-20 | 1975-12-19 | Water-soluble disazo dyestuffs, a process for their preparation and their use for dyeing synthetic and natural polyamides |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5187532A (en, 2012) |
| BE (1) | BE836941A (en, 2012) |
| CA (1) | CA1064022A (en, 2012) |
| CH (1) | CH584266A5 (en, 2012) |
| DE (1) | DE2460467A1 (en, 2012) |
| FR (1) | FR2295085A1 (en, 2012) |
| GB (1) | GB1496560A (en, 2012) |
| IT (1) | IT1051387B (en, 2012) |
| NL (1) | NL7514578A (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0944674A1 (en) * | 1996-11-20 | 1999-09-29 | CROMPTON & KNOWLES CORPORATION | Acid yellow dye and method for using same |
-
1974
- 1974-12-20 DE DE19742460467 patent/DE2460467A1/de not_active Withdrawn
-
1975
- 1975-12-04 GB GB4982675A patent/GB1496560A/en not_active Expired
- 1975-12-15 NL NL7514578A patent/NL7514578A/xx not_active Application Discontinuation
- 1975-12-17 CH CH1637175A patent/CH584266A5/xx not_active IP Right Cessation
- 1975-12-18 IT IT3047875A patent/IT1051387B/it active
- 1975-12-19 CA CA242,133A patent/CA1064022A/en not_active Expired
- 1975-12-19 JP JP15067275A patent/JPS5187532A/ja active Pending
- 1975-12-22 BE BE163004A patent/BE836941A/xx unknown
- 1975-12-22 FR FR7539262A patent/FR2295085A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2460467A1 (de) | 1976-07-01 |
| FR2295085A1 (fr) | 1976-07-16 |
| CH584266A5 (en, 2012) | 1977-01-31 |
| IT1051387B (it) | 1981-04-21 |
| BE836941A (fr) | 1976-06-22 |
| GB1496560A (en) | 1977-12-30 |
| NL7514578A (nl) | 1976-06-22 |
| JPS5187532A (ja) | 1976-07-31 |
| FR2295085B1 (en, 2012) | 1980-06-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3954395A (en) | Mixtures of dyestuffs | |
| US5519121A (en) | Triazinyl-amino bridge-containing disazo dyestuffs | |
| EP0253932B1 (en) | A water soluble direct black polyazo dyestuffs mixture | |
| US2979498A (en) | New monoazo dyestuffs | |
| CA1064022A (en) | Water-soluble disazo dyestuffs, a process for their preparation and their use for dyeing synthetic and natural polyamides | |
| US4621136A (en) | Phenyl azo cyanothienyl azo anilino dyestuffs | |
| US3900460A (en) | Water-soluble disazo compounds containing a pyrazole component | |
| US3454552A (en) | Disazo cationic dyestuffs containing a quaternary ammonium group | |
| US4149851A (en) | Concentrated aqueous dye compositions containing a low molecular weight amide | |
| US6042621A (en) | Fibre-reactive dyestuffs | |
| CA1059998A (en) | Water-soluble disazo dyestuffs, process for their preparation and their use | |
| US4052157A (en) | Use of water-soluble disazo dyestuffs for dyeing or printing synthetic textile material of polyamide or polyurethane fibers | |
| US4113719A (en) | 1:2-Cobalt-complex azo dyestuffs having an acetoacetylamino diphenylamino coupler | |
| US4194883A (en) | Water-soluble disazo dyestuffs and process for coloring synthetic polyamide fibres with them | |
| US4642339A (en) | Thiazoleazophenylaminoethyl carbonyloxy-C8 -C10 -alkyl compounds useful as dyes for polyester fibers | |
| KR20090056931A (ko) | 산 염료 | |
| US3939141A (en) | Water-soluble copper complex phenyl azo naphthalene reactive dyestuffs | |
| US3814749A (en) | Blue phenylazonaphthylazo-n-aryl peri acids | |
| JPH0635550B2 (ja) | モノアゾ染料 | |
| US3130190A (en) | Water insoluble monoazo dyestuffs | |
| US3624065A (en) | Water-soluble basic trialkyl ammonium phenylazopyrimidine | |
| US3491083A (en) | Azo dyestuffs for polyamide fibers containing a thiophenedioxide group | |
| US3881866A (en) | Polyester or polyacrylonitrile fibers dyed by quaternized or unquarternized azoanilino-toluene sulfonamidoalkyleneamine | |
| US5059682A (en) | Water-soluble phthalocyanine compounds, process for their preparation and their use | |
| US4077765A (en) | Monoazo-dyes particularly suited to the levelled dyeing of synthetic polyamide fibers |