DE1769175C3 - Wasserlösliche Polyazofarbstoffe, Verfahren zu ihrer Herstellung und deren Verwendung - Google Patents
Wasserlösliche Polyazofarbstoffe, Verfahren zu ihrer Herstellung und deren VerwendungInfo
- Publication number
- DE1769175C3 DE1769175C3 DE1769175A DE1769175A DE1769175C3 DE 1769175 C3 DE1769175 C3 DE 1769175C3 DE 1769175 A DE1769175 A DE 1769175A DE 1769175 A DE1769175 A DE 1769175A DE 1769175 C3 DE1769175 C3 DE 1769175C3
- Authority
- DE
- Germany
- Prior art keywords
- parts
- acid
- solution
- dye
- weight
- 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 52
- -1 polyazo Polymers 0.000 title claims description 28
- 238000000034 method Methods 0.000 title description 5
- 239000002253 acid Substances 0.000 claims description 15
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 15
- 229960001755 resorcinol Drugs 0.000 claims 1
- 239000000243 solution Substances 0.000 description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 16
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 12
- 125000001246 bromo group Chemical group Br* 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 11
- 235000011121 sodium hydroxide Nutrition 0.000 description 11
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 8
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 8
- 239000010985 leather Substances 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 235000010288 sodium nitrite Nutrition 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- 125000000542 sulfonic acid group Chemical group 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 6
- 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 6
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000012670 alkaline solution Substances 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- 235000002639 sodium chloride Nutrition 0.000 description 5
- 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 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 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 4
- 229950000244 sulfanilic acid Drugs 0.000 description 4
- 239000003086 colorant Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 2
- QJGHJWKPZQIOSN-UHFFFAOYSA-N (4-aminophenyl)methanesulfonic acid Chemical compound NC1=CC=C(CS(O)(=O)=O)C=C1 QJGHJWKPZQIOSN-UHFFFAOYSA-N 0.000 description 1
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 1
- POKNWSWQFXJOBG-UHFFFAOYSA-N 2-(3-aminophenyl)-5-methyl-1h-pyrazol-3-one Chemical compound N1C(C)=CC(=O)N1C1=CC=CC(N)=C1 POKNWSWQFXJOBG-UHFFFAOYSA-N 0.000 description 1
- WFNLHDJJZSJARK-UHFFFAOYSA-N 2-chloro-6-methylaniline Chemical compound CC1=CC=CC(Cl)=C1N WFNLHDJJZSJARK-UHFFFAOYSA-N 0.000 description 1
- IMUUNYPYNWXUBO-UHFFFAOYSA-N 4-aminobenzene-1,3-disulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1S(O)(=O)=O IMUUNYPYNWXUBO-UHFFFAOYSA-N 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 238000005406 washing Methods 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
- 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
- C09B33/28—Tetrazo dyes of the type A->B->K<-C<-D
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1769175A DE1769175C3 (de) | 1968-04-17 | 1968-04-17 | Wasserlösliche Polyazofarbstoffe, Verfahren zu ihrer Herstellung und deren Verwendung |
| NL6903889.A NL161799C (nl) | 1968-04-17 | 1969-03-13 | Werkwijze voor het bereiden van in water oplosbare polyazokleurstoffen, werkwijze voor het verven van leder en pelsvelours; alsmede aldus verkregen geverfde voorwerpen. |
| US814440A US3634390A (en) | 1968-04-17 | 1969-04-08 | Water-soluble tetraazo dyestuffs containing a pyrazolone and disulfonaphthal group |
| AT362069A AT283539B (de) | 1968-04-17 | 1969-04-15 | Verfahren zur Herstellung von neuen, wasserlöslichen Polyazofarbstoffen |
| CH567569A CH506594A (de) | 1968-04-17 | 1969-04-15 | Verfahren zur Herstellung wasserlöslicher Polyazofarbstoffe |
| GB1238780D GB1238780A (US07709020-20100504-C00041.png) | 1968-04-17 | 1969-04-16 | |
| FR6911964A FR2006380B1 (US07709020-20100504-C00041.png) | 1968-04-17 | 1969-04-17 | |
| BE731656D BE731656A (US07709020-20100504-C00041.png) | 1968-04-17 | 1969-04-17 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1769175A DE1769175C3 (de) | 1968-04-17 | 1968-04-17 | Wasserlösliche Polyazofarbstoffe, Verfahren zu ihrer Herstellung und deren Verwendung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1769175A1 DE1769175A1 (de) | 1971-10-21 |
| DE1769175B2 DE1769175B2 (de) | 1974-01-24 |
| DE1769175C3 true DE1769175C3 (de) | 1974-08-22 |
Family
ID=5700031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1769175A Expired DE1769175C3 (de) | 1968-04-17 | 1968-04-17 | Wasserlösliche Polyazofarbstoffe, Verfahren zu ihrer Herstellung und deren Verwendung |
Country Status (8)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4169831A (en) * | 1974-04-25 | 1979-10-02 | Produits Chimiques Ugine Kuhlmann | Water-soluble tetrakisazo dyestuffs derived from 4,4'-diaminoazobenzene |
| FR2268846B1 (US07709020-20100504-C00041.png) * | 1974-04-25 | 1976-10-15 | Ugine Kuhlmann | |
| DE3133552A1 (de) * | 1981-08-25 | 1983-03-17 | Hoechst Ag, 6000 Frankfurt | Neue wasserloesliche trisazofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung zum faerben von leder und pelz |
-
1968
- 1968-04-17 DE DE1769175A patent/DE1769175C3/de not_active Expired
-
1969
- 1969-03-13 NL NL6903889.A patent/NL161799C/xx not_active IP Right Cessation
- 1969-04-08 US US814440A patent/US3634390A/en not_active Expired - Lifetime
- 1969-04-15 AT AT362069A patent/AT283539B/de not_active IP Right Cessation
- 1969-04-15 CH CH567569A patent/CH506594A/de not_active IP Right Cessation
- 1969-04-16 GB GB1238780D patent/GB1238780A/en not_active Expired
- 1969-04-17 BE BE731656D patent/BE731656A/xx unknown
- 1969-04-17 FR FR6911964A patent/FR2006380B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH506594A (de) | 1971-04-30 |
| FR2006380B1 (US07709020-20100504-C00041.png) | 1973-11-16 |
| DE1769175A1 (de) | 1971-10-21 |
| US3634390A (en) | 1972-01-11 |
| NL161799C (nl) | 1980-03-17 |
| GB1238780A (US07709020-20100504-C00041.png) | 1971-07-07 |
| NL6903889A (US07709020-20100504-C00041.png) | 1969-10-21 |
| AT283539B (de) | 1970-08-10 |
| DE1769175B2 (de) | 1974-01-24 |
| FR2006380A1 (US07709020-20100504-C00041.png) | 1969-12-26 |
| NL161799B (nl) | 1979-10-15 |
| BE731656A (US07709020-20100504-C00041.png) | 1969-10-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |