DE2047025C3 - Wasserlösliche 1 zu 1-Kupferkomplex-Disazofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung zum Färben oder Bedrucken von nativen oder regenerierten Cellulosefaser«, Leder, Wolle, Seide, Polyamid- oder Polyurethanfasern - Google Patents
Wasserlösliche 1 zu 1-Kupferkomplex-Disazofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung zum Färben oder Bedrucken von nativen oder regenerierten Cellulosefaser«, Leder, Wolle, Seide, Polyamid- oder PolyurethanfasernInfo
- Publication number
- DE2047025C3 DE2047025C3 DE19702047025 DE2047025A DE2047025C3 DE 2047025 C3 DE2047025 C3 DE 2047025C3 DE 19702047025 DE19702047025 DE 19702047025 DE 2047025 A DE2047025 A DE 2047025A DE 2047025 C3 DE2047025 C3 DE 2047025C3
- Authority
- DE
- Germany
- Prior art keywords
- parts
- water
- amino
- weight
- methoxy
- 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 50
- 238000004043 dyeing Methods 0.000 title description 12
- 238000000034 method Methods 0.000 title description 9
- 229920003043 Cellulose fiber Polymers 0.000 title description 3
- 239000004952 Polyamide Substances 0.000 title description 3
- 229920002647 polyamide Polymers 0.000 title description 3
- 229920006306 polyurethane fiber Polymers 0.000 title description 3
- 239000004627 regenerated cellulose Substances 0.000 title description 3
- 210000002268 wool Anatomy 0.000 title description 3
- 239000010985 leather Substances 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 naphthyl radical Chemical class 0.000 description 38
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 26
- 239000002253 acid Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 23
- 239000010949 copper Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 19
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000001103 potassium chloride Substances 0.000 description 13
- 235000011164 potassium chloride Nutrition 0.000 description 13
- 230000008878 coupling Effects 0.000 description 12
- 238000010168 coupling process Methods 0.000 description 12
- 238000005859 coupling reaction Methods 0.000 description 12
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 229920000742 Cotton Polymers 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 239000000843 powder Substances 0.000 description 7
- 238000011282 treatment Methods 0.000 description 6
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 5
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 5
- 239000012065 filter cake Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910000365 copper sulfate Inorganic materials 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 238000005185 salting out Methods 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000001879 copper Chemical class 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 150000004699 copper complex Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 125000001174 sulfone group Chemical group 0.000 description 3
- ZUQOBHTUMCEQBG-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 ZUQOBHTUMCEQBG-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000001465 metallisation Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 230000002085 persistent effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 1
- OBEQWTGDHGJFQR-UHFFFAOYSA-N 3-acetamido-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(NC(=O)C)=CC2=C1O OBEQWTGDHGJFQR-UHFFFAOYSA-N 0.000 description 1
- USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 description 1
- ZFRBZRZEKIOGQI-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound C1=CC(O)=C2C(N)=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1 ZFRBZRZEKIOGQI-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
- 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
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- VILFVXYKHXVYAB-UHFFFAOYSA-N naphthalene-2,7-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 VILFVXYKHXVYAB-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000002270 phosphoric acid ester group Chemical group 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000002130 sulfonic acid ester group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
- C09B62/507—Azo dyes
- C09B62/515—Metal complex azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19702047025 DE2047025C3 (de) | 1970-09-24 | 1970-09-24 | Wasserlösliche 1 zu 1-Kupferkomplex-Disazofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung zum Färben oder Bedrucken von nativen oder regenerierten Cellulosefaser«, Leder, Wolle, Seide, Polyamid- oder Polyurethanfasern |
CS650071A CS165361B2 (enrdf_load_stackoverflow) | 1970-09-24 | 1971-09-10 | |
ES395205A ES395205A1 (es) | 1970-09-24 | 1971-09-18 | Procedimiento para la preparacion de colorantes disazoicos solubles en agua. |
CH1378371A CH565846A5 (enrdf_load_stackoverflow) | 1970-09-24 | 1971-09-21 | |
AU33765/71A AU465069B2 (en) | 1970-09-24 | 1971-09-22 | Reactive disazo dyestuffs, and metal complex compounds prepared thereof and process for their manufacture |
CA123,511A CA953711A (en) | 1970-09-24 | 1971-09-23 | Water-soluble, fibre-reactive disazo dyestuffs, and metal complex compounds prepared thereof, and process for their manufacture |
BR629571A BR7106295D0 (pt) | 1970-09-24 | 1971-09-23 | Processo para preparacao de corantes disazoicos hidrossoluveis e de seus corantes disazoicos contendo metais |
GB4471671A GB1370456A (en) | 1970-09-24 | 1971-09-24 | Water-soluble disazo dyestuffs metal complexes thereof and process for their manufacture |
FR7134470A FR2107951B1 (enrdf_load_stackoverflow) | 1970-09-24 | 1971-09-24 | |
BE773034A BE773034A (fr) | 1970-09-24 | 1971-09-24 | Colorants disazoiques, complexes de metaux de ces colorants et preparation de ces produits |
US05/718,835 US4185012A (en) | 1970-09-24 | 1976-08-30 | Water-soluble, fibre-reactive copper complex disazo dyestuffs |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19702047025 DE2047025C3 (de) | 1970-09-24 | 1970-09-24 | Wasserlösliche 1 zu 1-Kupferkomplex-Disazofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung zum Färben oder Bedrucken von nativen oder regenerierten Cellulosefaser«, Leder, Wolle, Seide, Polyamid- oder Polyurethanfasern |
Publications (3)
Publication Number | Publication Date |
---|---|
DE2047025A1 DE2047025A1 (de) | 1972-03-30 |
DE2047025B2 DE2047025B2 (de) | 1978-10-26 |
DE2047025C3 true DE2047025C3 (de) | 1979-06-21 |
Family
ID=5783260
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19702047025 Expired DE2047025C3 (de) | 1970-09-24 | 1970-09-24 | Wasserlösliche 1 zu 1-Kupferkomplex-Disazofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung zum Färben oder Bedrucken von nativen oder regenerierten Cellulosefaser«, Leder, Wolle, Seide, Polyamid- oder Polyurethanfasern |
Country Status (10)
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4185012A (en) * | 1970-09-24 | 1980-01-22 | Hoechst Aktiengesellschaft | Water-soluble, fibre-reactive copper complex disazo dyestuffs |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1285552A (fr) * | 1961-03-11 | 1962-02-23 | Ici Ltd | Nouveaux colorants azoïques métallisés |
FR1331888A (fr) * | 1962-08-24 | 1963-07-05 | Bayer Ag | Colorants azoïques métallifères, leur procédé de préparation et leur application |
FR1372362A (fr) * | 1962-10-26 | 1964-09-11 | Hoechst Ag | Colorants azoiques solubles dans l'eau et leur préparation |
-
1970
- 1970-09-24 DE DE19702047025 patent/DE2047025C3/de not_active Expired
-
1971
- 1971-09-10 CS CS650071A patent/CS165361B2/cs unknown
- 1971-09-18 ES ES395205A patent/ES395205A1/es not_active Expired
- 1971-09-21 CH CH1378371A patent/CH565846A5/xx not_active IP Right Cessation
- 1971-09-22 AU AU33765/71A patent/AU465069B2/en not_active Expired
- 1971-09-23 BR BR629571A patent/BR7106295D0/pt unknown
- 1971-09-23 CA CA123,511A patent/CA953711A/en not_active Expired
- 1971-09-24 FR FR7134470A patent/FR2107951B1/fr not_active Expired
- 1971-09-24 GB GB4471671A patent/GB1370456A/en not_active Expired
- 1971-09-24 BE BE773034A patent/BE773034A/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
ES395205A1 (es) | 1973-11-01 |
FR2107951A1 (enrdf_load_stackoverflow) | 1972-05-12 |
CS165361B2 (enrdf_load_stackoverflow) | 1975-12-22 |
GB1370456A (en) | 1974-10-16 |
DE2047025B2 (de) | 1978-10-26 |
BR7106295D0 (pt) | 1973-05-03 |
FR2107951B1 (enrdf_load_stackoverflow) | 1976-03-26 |
AU465069B2 (en) | 1975-09-18 |
DE2047025A1 (de) | 1972-03-30 |
BE773034A (fr) | 1972-03-24 |
CH565846A5 (enrdf_load_stackoverflow) | 1975-08-29 |
AU3376571A (en) | 1973-03-29 |
CA953711A (en) | 1974-08-27 |
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