DE2533250C3 - Verfahren zur Herstellung von wasserlöslichen Kupferkomplex-Azofarbstoffen und ihre Verwendung zum Färben von CeUulosefasermaterialien - Google Patents
Verfahren zur Herstellung von wasserlöslichen Kupferkomplex-Azofarbstoffen und ihre Verwendung zum Färben von CeUulosefasermaterialienInfo
- Publication number
- DE2533250C3 DE2533250C3 DE2533250A DE2533250A DE2533250C3 DE 2533250 C3 DE2533250 C3 DE 2533250C3 DE 2533250 A DE2533250 A DE 2533250A DE 2533250 A DE2533250 A DE 2533250A DE 2533250 C3 DE2533250 C3 DE 2533250C3
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compound
- acid
- water
- dyes
- 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
- 238000000034 method Methods 0.000 title claims description 33
- 238000004043 dyeing Methods 0.000 title claims description 17
- 239000000987 azo dye Substances 0.000 title claims description 9
- 150000004699 copper complex Chemical class 0.000 title claims description 8
- 229920003043 Cellulose fiber Polymers 0.000 title claims description 7
- 239000002657 fibrous material Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000000975 dye Substances 0.000 claims description 35
- 239000002253 acid Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 11
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 229910052802 copper Inorganic materials 0.000 claims description 8
- 239000010949 copper Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 229910052910 alkali metal silicate Inorganic materials 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000032050 esterification Effects 0.000 claims description 4
- 238000007747 plating Methods 0.000 claims description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 150000007933 aliphatic carboxylic acids Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 2
- 230000001180 sulfating effect Effects 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 150000001879 copper Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000003513 alkali Substances 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000000985 reactive dye Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 235000011132 calcium sulphate Nutrition 0.000 description 2
- -1 copper complex azo compound Chemical class 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000003032 molecular docking Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- FTCOWMWIZNVSPP-UHFFFAOYSA-N 2-phenyl-4h-pyrazol-3-one Chemical compound O=C1CC=NN1C1=CC=CC=C1 FTCOWMWIZNVSPP-UHFFFAOYSA-N 0.000 description 1
- YCTAOQGPWNTYJE-UHFFFAOYSA-N 3-amino-5-chloro-2-hydroxybenzenesulfonic acid Chemical compound NC1=CC(Cl)=CC(S(O)(=O)=O)=C1O YCTAOQGPWNTYJE-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 244000299507 Gossypium hirsutum Species 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000907663 Siproeta stelenes Species 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000000159 acid neutralizing agent Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000001175 calcium sulphate Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910000009 copper(II) carbonate Inorganic materials 0.000 description 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000011646 cupric carbonate Substances 0.000 description 1
- 235000019854 cupric carbonate Nutrition 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- YNLZKJXZEZFHDO-UHFFFAOYSA-M potassium;2,2,2-trichloroacetate Chemical compound [K+].[O-]C(=O)C(Cl)(Cl)Cl YNLZKJXZEZFHDO-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/18—Monoazo compounds containing copper
-
- 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/34—Preparation from o-monohydroxy azo compounds having in the o'-position an atom or functional group other than hydroxyl, alkoxy, carboxyl, amino or keto groups
- C09B45/36—Preparation from o-monohydroxy azo compounds having in the o'-position an atom or functional group other than hydroxyl, alkoxy, carboxyl, amino or keto groups by oxidation of hydrogen in o'-position
-
- 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 |
|---|---|---|---|
| DE2533250A DE2533250C3 (de) | 1975-07-25 | 1975-07-25 | Verfahren zur Herstellung von wasserlöslichen Kupferkomplex-Azofarbstoffen und ihre Verwendung zum Färben von CeUulosefasermaterialien |
| BR7604745A BR7604745A (pt) | 1975-07-25 | 1976-07-21 | Complexos de cobre hidrossoluveis,processo para sua preparacao,sua aplicacao,e materiais fibrosos tingidos ou estampados os mesmos |
| CH939276A CH630214GA3 (en) | 1975-07-25 | 1976-07-22 | Process for the preparation of water-soluble copper complex dyes and their use |
| CS7600004885A CS186742B2 (en) | 1975-07-25 | 1976-07-23 | Method of dyeing and printing fibrous materials |
| IT25680/76A IT1064732B (it) | 1975-07-25 | 1976-07-23 | Complessi di rame idrosolubili processo per la loro preparazione e loro impiego come coloranti |
| AU16185/76A AU501564B2 (en) | 1975-07-25 | 1976-07-23 | Coppering azo dyes |
| IN1319/CAL/1976A IN144645B (enExample) | 1975-07-25 | 1976-07-23 | |
| JP51087752A JPS605621B2 (ja) | 1975-07-25 | 1976-07-24 | 水溶性銅錯体染料の製法 |
| FR7622744A FR2318906A1 (fr) | 1975-07-25 | 1976-07-26 | Procede de preparation de complexes hydrosolubles du cuivre utilisables comme colorants |
| BE169249A BE844527A (fr) | 1975-07-25 | 1976-07-26 | Procede de preparation de complexes hydrosolubles du cuivre utilisables comme colorants |
| GB31051/76A GB1508700A (en) | 1975-07-25 | 1976-07-26 | Water-soluble copper complex compounds process for their preparation and use as dyestuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2533250A DE2533250C3 (de) | 1975-07-25 | 1975-07-25 | Verfahren zur Herstellung von wasserlöslichen Kupferkomplex-Azofarbstoffen und ihre Verwendung zum Färben von CeUulosefasermaterialien |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2533250A1 DE2533250A1 (de) | 1977-01-27 |
| DE2533250B2 DE2533250B2 (de) | 1978-11-23 |
| DE2533250C3 true DE2533250C3 (de) | 1979-07-26 |
Family
ID=5952432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2533250A Expired DE2533250C3 (de) | 1975-07-25 | 1975-07-25 | Verfahren zur Herstellung von wasserlöslichen Kupferkomplex-Azofarbstoffen und ihre Verwendung zum Färben von CeUulosefasermaterialien |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS605621B2 (enExample) |
| AU (1) | AU501564B2 (enExample) |
| BE (1) | BE844527A (enExample) |
| BR (1) | BR7604745A (enExample) |
| CH (1) | CH630214GA3 (enExample) |
| CS (1) | CS186742B2 (enExample) |
| DE (1) | DE2533250C3 (enExample) |
| FR (1) | FR2318906A1 (enExample) |
| GB (1) | GB1508700A (enExample) |
| IN (1) | IN144645B (enExample) |
| IT (1) | IT1064732B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6247314U (enExample) * | 1985-09-12 | 1987-03-24 | ||
| JPH01127512U (enExample) * | 1988-02-17 | 1989-08-31 | ||
| JP2599526B2 (ja) * | 1992-02-03 | 1997-04-09 | 新日本製鐵株式会社 | 特性異方性の小さいバネ限界値と強度に優れた銅−鉄系金属薄板およびその製造方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1285552A (fr) * | 1961-03-11 | 1962-02-23 | Ici Ltd | Nouveaux colorants azoïques métallisés |
| DE2016862C3 (de) * | 1970-04-09 | 1980-02-07 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von I zu 1- und I zu 2-Metailkomplexazofarbstoffen |
-
1975
- 1975-07-25 DE DE2533250A patent/DE2533250C3/de not_active Expired
-
1976
- 1976-07-21 BR BR7604745A patent/BR7604745A/pt unknown
- 1976-07-22 CH CH939276A patent/CH630214GA3/de unknown
- 1976-07-23 CS CS7600004885A patent/CS186742B2/cs unknown
- 1976-07-23 IT IT25680/76A patent/IT1064732B/it active
- 1976-07-23 IN IN1319/CAL/1976A patent/IN144645B/en unknown
- 1976-07-23 AU AU16185/76A patent/AU501564B2/en not_active Expired
- 1976-07-24 JP JP51087752A patent/JPS605621B2/ja not_active Expired
- 1976-07-26 GB GB31051/76A patent/GB1508700A/en not_active Expired
- 1976-07-26 BE BE169249A patent/BE844527A/xx not_active IP Right Cessation
- 1976-07-26 FR FR7622744A patent/FR2318906A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CH630214B (de) | |
| JPS605621B2 (ja) | 1985-02-13 |
| IN144645B (enExample) | 1978-05-27 |
| FR2318906A1 (fr) | 1977-02-18 |
| CS186742B2 (en) | 1978-12-29 |
| GB1508700A (en) | 1978-04-26 |
| CH630214GA3 (en) | 1982-06-15 |
| JPS5215524A (en) | 1977-02-05 |
| DE2533250A1 (de) | 1977-01-27 |
| BE844527A (fr) | 1977-01-26 |
| AU501564B2 (en) | 1979-06-21 |
| BR7604745A (pt) | 1977-08-02 |
| DE2533250B2 (de) | 1978-11-23 |
| IT1064732B (it) | 1985-02-25 |
| FR2318906B1 (enExample) | 1981-04-17 |
| AU1618576A (en) | 1978-01-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0028788B1 (de) | Kupferkomplex-Formazanverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbstoffe | |
| DE1210105B (de) | Verfahren zur Herstellung metallhaltiger Reaktivfarbstoffe | |
| DE1544539C3 (de) | Metallkomplex-Disazofarbstoffe und Verfahren zu ihrer Herstellung | |
| DE1544538C3 (de) | Metallkomplex-Disazofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung | |
| DE2533250C3 (de) | Verfahren zur Herstellung von wasserlöslichen Kupferkomplex-Azofarbstoffen und ihre Verwendung zum Färben von CeUulosefasermaterialien | |
| DE1644155B2 (de) | Verfahren zur herstellung von disazofarbstoffen und deren metallkomplexverbindungen | |
| DE2431343C2 (de) | Goldgelbe, wasserlösliche Monoazoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbstoffe | |
| EP0534342A1 (de) | Wasserlösliche Monoazoverbindungen, Verfahren zu deren Herstellung und ihre Verwendung als Farbstoffe | |
| DE2034591C3 (de) | Wasserlösliche Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben und Bedrucken von Leder oder Fasermaterialien aus Wolle, Seide, Polyamiden und Polyurethanen und/oder nativer oder regenerierter Zellulose | |
| EP0133283A1 (de) | Wasserlösliche Disazoverbindungen, Verfahren zu deren Herstellung und ihre Verwendung als Farbstoffe | |
| DE1644161C3 (de) | Wasserlösliche, kupferhaltige Monoazoreaktivfarbstoffe, Verfahren zu deren Herstellung und Verwendung dieser Farbstoffe zum Färben oder Bedrucken von Materialien aus Cellulose, Wolle oder Polyamidfasern | |
| DE1127322C2 (de) | Verfahren zum Faerben und Bedrucken von Cellulosetextilmaterialien | |
| DE1544541C3 (enExample) | ||
| DE1245515B (de) | Verfahren zur Herstellung wasserloeslicher reaktiver Disazofarbstoffe | |
| DE2239919C3 (de) | Kupferhaltige, faserreaktive Disazoverbindungen, ihre Herstellung und Verwendung zum Färben und Bedrucken von natürlicher und regenerierter Cellulose | |
| DE2047025C3 (de) | 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 | |
| DE2417670C2 (de) | Wasserlösliche Monoazoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbstoffe | |
| DE1242553B (de) | Verfahren zur Herstellung von echten Faerbungen oder Drucken auf Fasern oder Geweben aus natuerlicher oder regenerierter Cellulose | |
| DE1904113B2 (de) | Faserreaktive, schwermetallhaltige Formazanfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung | |
| DE1644353C (de) | Verfahren zur Herstellung wasserlos hcher, kupferhaltiger Reaktivfarbstoffe | |
| DE2308068C3 (de) | Monoazo-Verblndungen, Verfahren zu deren Herstellung und Ihre Verwendung als Farbstoffe | |
| DE2061358B2 (de) | Wasserlösliche Metallkomplexmonoazofarbstoffe, Verfahren zur ihrer Herstellung und ihre Verwendung zum Färben oder Bedrucken von Fasermaterialien aus nativer oder regenerierter Cellulose, natürlichen stickstoffhaltigen Fasern und Polyamid- und Polyurethanfasern | |
| DE1793275C3 (de) | Neue, wasserlösliche Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE1444675A1 (de) | Verfahren zur Herstellung von reaktiven Azofarbstoffen | |
| DE1769020A1 (de) | Faserreaktive kupferhaltige Monoazofarbstoffe |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |