DE2616856C2 - Organische Verbindungen, deren Herstellung und Verwendung - Google Patents
Organische Verbindungen, deren Herstellung und VerwendungInfo
- Publication number
- DE2616856C2 DE2616856C2 DE2616856A DE2616856A DE2616856C2 DE 2616856 C2 DE2616856 C2 DE 2616856C2 DE 2616856 A DE2616856 A DE 2616856A DE 2616856 A DE2616856 A DE 2616856A DE 2616856 C2 DE2616856 C2 DE 2616856C2
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- parts
- formula
- chr
- methyl
- 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
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000002894 organic compounds Chemical class 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims description 70
- 239000001257 hydrogen Substances 0.000 claims description 68
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 238000002360 preparation method Methods 0.000 claims description 27
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000975 dye Substances 0.000 description 68
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 49
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 17
- 239000000725 suspension Substances 0.000 description 17
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 238000004043 dyeing Methods 0.000 description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
- 235000002639 sodium chloride Nutrition 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- 150000004820 halides Chemical class 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 7
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 7
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 235000010288 sodium nitrite Nutrition 0.000 description 6
- -1 sulpho groups Chemical group 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000008187 granular material Substances 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
- 239000011541 reaction mixture Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 230000000740 bleeding effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 1
- 235000018185 Betula X alpestris Nutrition 0.000 description 1
- 235000018212 Betula X uliginosa Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007970 homogeneous dispersion Substances 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 239000010979 ruby Substances 0.000 description 1
- 229910001750 ruby Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- SRWFBFUYENBCGF-UHFFFAOYSA-M sodium;chloride;hydrochloride Chemical compound [Na+].Cl.[Cl-] SRWFBFUYENBCGF-UHFFFAOYSA-M 0.000 description 1
- 239000011122 softwood Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000002023 wood 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
- C09B62/78—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 with other reactive groups
- C09B62/82—Azo dyes
- C09B62/83—Disazo or polyazo 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
- C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
-
- 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
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
- C09B43/1242—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters with heterocyclic monocarboxylic acids
-
- 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
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
- C09B43/16—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Paper (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH527775A CH601437A5 (en, 2012) | 1975-04-24 | 1975-04-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2616856A1 DE2616856A1 (de) | 1976-11-04 |
| DE2616856C2 true DE2616856C2 (de) | 1984-07-12 |
Family
ID=4290895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2616856A Expired DE2616856C2 (de) | 1975-04-24 | 1976-04-15 | Organische Verbindungen, deren Herstellung und Verwendung |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4083840A (en, 2012) |
| JP (1) | JPS5945013B2 (en, 2012) |
| BE (1) | BE841017A (en, 2012) |
| BR (1) | BR7602517A (en, 2012) |
| CA (1) | CA1066271A (en, 2012) |
| CH (1) | CH601437A5 (en, 2012) |
| DE (1) | DE2616856C2 (en, 2012) |
| FI (1) | FI761044A7 (en, 2012) |
| FR (1) | FR2309604A1 (en, 2012) |
| GB (1) | GB1537767A (en, 2012) |
| IT (1) | IT1060256B (en, 2012) |
| NO (1) | NO142675C (en, 2012) |
| SE (1) | SE411220B (en, 2012) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2915323A1 (de) * | 1978-04-26 | 1979-11-08 | Sandoz Ag | Basische bzw. kationische, sulfonsaeuregruppenhaltige monoazo- oder disazoverbindungen |
| JPS56155250A (en) | 1980-04-10 | 1981-12-01 | Nippon Kayaku Co Ltd | Reactive dis-azo compound, production thereof and dyeing method employing the same |
| JPS612762A (ja) * | 1984-06-14 | 1986-01-08 | Sumitomo Chem Co Ltd | ジスアゾ化合物およびそれを用いる染色または捺染法 |
| GB8421551D0 (en) * | 1984-08-24 | 1984-09-26 | Ici Plc | Water-soluble dye |
| CH668977A5 (de) * | 1985-08-19 | 1989-02-15 | Sandoz Ag | Basische, sulfonsaeuregruppenhaltige monoazo- oder disazoverbindungen. |
| CH671024A5 (en, 2012) * | 1986-04-17 | 1989-07-31 | Sandoz Ag | |
| JPH0762112B2 (ja) * | 1987-03-31 | 1995-07-05 | 日本化薬株式会社 | ジスアゾ化合物及びそれを用いる基材の染色法 |
| DE3876677D1 (de) * | 1987-04-27 | 1993-01-28 | Ciba Geigy Ag | Anionische disazofarbstoffe. |
| DE3887561D1 (de) * | 1987-04-27 | 1994-03-17 | Ciba Geigy | Anionische Disazofarbstoffe. |
| CH679723B5 (en, 2012) * | 1988-03-09 | 1992-10-15 | Ciba Geigy Ag | |
| US5203912A (en) * | 1988-08-24 | 1993-04-20 | Imperial Chemical Industries Plc | Anionic dye |
| GB8917764D0 (en) * | 1988-08-24 | 1989-09-20 | Ici Plc | Anionic dye |
| US5198022A (en) * | 1991-10-25 | 1993-03-30 | Lexmark International, Inc. | Waterfast dye and aqueous ink |
| JP3162834B2 (ja) * | 1991-10-25 | 2001-05-08 | レックスマーク・インターナショナル・インコーポレーテツド | 耐水性染料および水性インク |
| US5466282A (en) * | 1993-05-18 | 1995-11-14 | Canon Kabushiki Kaisha | Azo dye compound, ink containing the same, and recording method and instrument using the ink |
| US5795970A (en) * | 1995-08-25 | 1998-08-18 | Orient Chemical Industries, Ltd. | Mixed disazo-dye composition and black aqueous ink composition containing the same that provides high grade image on print |
| US6520384B2 (en) * | 2001-04-30 | 2003-02-18 | Ketan C. Mehta | Apparatus and method for nasal rinse |
| EP1587854A1 (en) * | 2003-01-17 | 2005-10-26 | Clariant International Ltd. | Polymeric etheramines, their production and use |
| EP1702099A2 (en) * | 2003-12-29 | 2006-09-20 | Clariant International Ltd. | Use of polymeric etheramines for improving the chlorine fastness of textiles |
| USD634631S1 (en) | 2009-12-16 | 2011-03-22 | Water Pik, Inc. | Nozzle and collar |
| USD653953S1 (en) | 2009-12-16 | 2012-02-14 | Water Pik, Inc. | Squeeze bottle |
| US8991660B2 (en) * | 2009-12-16 | 2015-03-31 | Water Pik, Inc. | Squeeze bottle for sinus cavity rinse |
| USD634630S1 (en) | 2009-12-16 | 2011-03-22 | Water Pik, Inc. | Nozzle |
| USD676126S1 (en) | 2010-06-25 | 2013-02-12 | Water Pik, Inc. | Faceted nasal seal |
| USD630314S1 (en) | 2009-12-16 | 2011-01-04 | Water Pik, Inc. | Vessel with handle for sinus cavity rinse |
| USD676125S1 (en) | 2010-06-25 | 2013-02-12 | Water Pik, Inc. | Faceted nasal seal with bottom rim |
| US8888752B2 (en) * | 2009-12-16 | 2014-11-18 | Water Pik, Inc. | Bottle for sinus cavity rinse |
| USD629884S1 (en) | 2009-12-16 | 2010-12-28 | Water Pik, Inc. | Powered irrigator for sinus cavity rinse |
| US8486029B2 (en) * | 2009-12-16 | 2013-07-16 | Water Pik, Inc. | Pot for sinus cavity rinse |
| US9061096B2 (en) | 2009-12-16 | 2015-06-23 | Water Pik, Inc. | Powered irrigator for sinus cavity rinse |
| USD627458S1 (en) | 2009-12-16 | 2010-11-16 | Water Pik, Inc. | Vessel for sinus cavity rinse |
| US8409152B2 (en) | 2010-06-25 | 2013-04-02 | Water Pik, Inc. | Faceted nasal seal |
| USD670373S1 (en) | 2010-12-16 | 2012-11-06 | Water Pik, Inc. | Powered irrigator for sinus cavity rinse |
| CN103911018B (zh) * | 2014-03-21 | 2016-01-20 | 沈阳化工大学 | 一种制备直接红253的方法 |
| CN112226098A (zh) * | 2019-07-15 | 2021-01-15 | 上海汇友精密化学品有限公司 | 一种直接染料及其制备方法 |
| CN117070077B (zh) * | 2023-08-17 | 2024-12-03 | 浙江闰土染料有限公司 | 红色直接染料及其制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE237742C (en, 2012) * | ||||
| DE229303C (en, 2012) * | ||||
| US2722527A (en) * | 1953-07-09 | 1955-11-01 | Sandoz Ag | Disazo dyestuffs |
| US3072454A (en) * | 1960-07-07 | 1963-01-08 | American Cyanamid Co | Reactive dyes containing methylolamide triazine groups |
| US3165506A (en) * | 1960-08-12 | 1965-01-12 | Ciba Geigy Corp | Disazo dyestuffs containing a trisulfonate diazo component |
| CH369843A (de) * | 1960-08-18 | 1963-06-15 | Ciba Geigy | Verfahren zur Herstellung von Azofarbstoffen |
| AT238342B (de) * | 1961-11-06 | 1965-02-10 | Ciba Geigy | Verfahren zur Herstellung neuer Disazofarbstoffe |
| US3635944A (en) * | 1969-05-12 | 1972-01-18 | Allied Chem | Highly water soluble disazo dyestuffs |
| DE2058816C3 (de) * | 1970-11-30 | 1975-02-06 | Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt | Wasserlöslicher Disazofarbstoff, Verfahren zu seiner Herstellung und seine Verwendung zum Färben von Leder und Pelz |
-
1975
- 1975-04-24 CH CH527775A patent/CH601437A5/xx not_active IP Right Cessation
-
1976
- 1976-04-14 SE SE7604386A patent/SE411220B/xx not_active IP Right Cessation
- 1976-04-14 NO NO761296A patent/NO142675C/no unknown
- 1976-04-15 DE DE2616856A patent/DE2616856C2/de not_active Expired
- 1976-04-15 FI FI761044A patent/FI761044A7/fi not_active Application Discontinuation
- 1976-04-19 US US05/678,105 patent/US4083840A/en not_active Expired - Lifetime
- 1976-04-20 GB GB15851/76A patent/GB1537767A/en not_active Expired
- 1976-04-22 JP JP51045010A patent/JPS5945013B2/ja not_active Expired
- 1976-04-22 BE BE166381A patent/BE841017A/xx not_active IP Right Cessation
- 1976-04-22 CA CA250,776A patent/CA1066271A/en not_active Expired
- 1976-04-23 BR BR2517/76A patent/BR7602517A/pt unknown
- 1976-04-23 IT IT22630/76A patent/IT1060256B/it active
- 1976-04-26 FR FR7612232A patent/FR2309604A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB1537767A (en) | 1979-01-04 |
| CA1066271A (en) | 1979-11-13 |
| BR7602517A (pt) | 1976-10-19 |
| DE2616856A1 (de) | 1976-11-04 |
| NO761296L (en, 2012) | 1976-10-26 |
| SE411220B (sv) | 1979-12-10 |
| NO142675C (no) | 1980-09-24 |
| US4083840A (en) | 1978-04-11 |
| IT1060256B (it) | 1982-07-10 |
| SE7604386L (sv) | 1976-10-25 |
| FR2309604B1 (en, 2012) | 1979-09-07 |
| JPS51138720A (en) | 1976-11-30 |
| NO142675B (no) | 1980-06-16 |
| FI761044A7 (en, 2012) | 1976-10-25 |
| JPS5945013B2 (ja) | 1984-11-02 |
| BE841017A (fr) | 1976-10-22 |
| AU1331976A (en) | 1977-10-27 |
| CH601437A5 (en, 2012) | 1978-07-14 |
| FR2309604A1 (fr) | 1976-11-26 |
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