JPS5945013B2 - ジスアゾ化合物 - Google Patents
ジスアゾ化合物Info
- Publication number
- JPS5945013B2 JPS5945013B2 JP51045010A JP4501076A JPS5945013B2 JP S5945013 B2 JPS5945013 B2 JP S5945013B2 JP 51045010 A JP51045010 A JP 51045010A JP 4501076 A JP4501076 A JP 4501076A JP S5945013 B2 JPS5945013 B2 JP S5945013B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- hydrogen
- methyl
- group
- formulas
- 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
- -1 Disazo compound Chemical class 0.000 title description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 91
- 239000001257 hydrogen Substances 0.000 claims description 91
- 150000001875 compounds Chemical class 0.000 claims description 70
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 53
- 150000002431 hydrogen Chemical class 0.000 claims description 47
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 238000004043 dyeing Methods 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 238000005859 coupling reaction Methods 0.000 claims description 10
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 9
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 9
- 150000001768 cations Chemical class 0.000 claims description 9
- 230000008878 coupling Effects 0.000 claims description 9
- 238000010168 coupling process Methods 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 35
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 3
- 239000000975 dye Substances 0.000 description 57
- 239000000243 solution Substances 0.000 description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 239000000203 mixture Substances 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- 239000000725 suspension Substances 0.000 description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
- 238000009472 formulation Methods 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 15
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 15
- 125000001424 substituent group Chemical group 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 11
- 235000002639 sodium chloride Nutrition 0.000 description 11
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000000843 powder Substances 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
- 239000007788 liquid Substances 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000010186 staining Methods 0.000 description 4
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- 239000012669 liquid formulation Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 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
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 2
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 2
- 229910052808 lithium carbonate Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000003254 radicals Chemical group 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 2
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 241000282821 Hippopotamus Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241000219745 Lupinus Species 0.000 description 1
- 241000159606 Netrium Species 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001298 alcohols Chemical class 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
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000007970 homogeneous dispersion Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 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
- 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
- 239000008267 milk Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000011122 softwood Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000003643 water by type 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 |
|---|---|
| JPS51138720A JPS51138720A (en) | 1976-11-30 |
| JPS5945013B2 true JPS5945013B2 (ja) | 1984-11-02 |
Family
ID=4290895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51045010A Expired JPS5945013B2 (ja) | 1975-04-24 | 1976-04-22 | ジスアゾ化合物 |
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 |
| DE2616856C2 (de) | 1984-07-12 |
| 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 |
| 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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