TW200427784A - Preparation of a liquid formulation of salts of sulfonated azo dyes - Google Patents
Preparation of a liquid formulation of salts of sulfonated azo dyes Download PDFInfo
- Publication number
- TW200427784A TW200427784A TW092133584A TW92133584A TW200427784A TW 200427784 A TW200427784 A TW 200427784A TW 092133584 A TW092133584 A TW 092133584A TW 92133584 A TW92133584 A TW 92133584A TW 200427784 A TW200427784 A TW 200427784A
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- Prior art keywords
- acid
- mono
- dye
- parts
- scope
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- 150000003839 salts Chemical class 0.000 title claims abstract description 21
- 239000012669 liquid formulation Substances 0.000 title claims abstract description 19
- 239000000987 azo dye Substances 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims abstract description 50
- 239000002253 acid Substances 0.000 claims abstract description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 4
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229940018564 m-phenylenediamine Drugs 0.000 claims abstract description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 40
- -1 caprolactone Amines Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 11
- 239000000654 additive Substances 0.000 claims description 9
- 230000003381 solubilizing effect Effects 0.000 claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 6
- 239000004202 carbamide Substances 0.000 claims description 6
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 claims 1
- 229960004050 aminobenzoic acid Drugs 0.000 claims 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N aniline-p-carboxylic acid Natural products NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims 1
- 229910052797 bismuth Inorganic materials 0.000 claims 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims 1
- 238000010586 diagram Methods 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- 230000000750 progressive effect Effects 0.000 claims 1
- 229960004418 trolamine Drugs 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 abstract description 16
- 230000008878 coupling Effects 0.000 abstract description 10
- 238000010168 coupling process Methods 0.000 abstract description 10
- 150000007513 acids Chemical class 0.000 abstract description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 2
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 239000000243 solution Substances 0.000 description 25
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 23
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 229950000244 sulfanilic acid Drugs 0.000 description 11
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 238000004043 dyeing Methods 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 8
- 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 7
- 238000005352 clarification Methods 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 150000003863 ammonium salts Chemical class 0.000 description 6
- 238000012812 general test Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
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- 235000010288 sodium nitrite Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
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- 238000000926 separation method Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- UCTREIIEJSFTDI-UHFFFAOYSA-N 3-aminonaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1 UCTREIIEJSFTDI-UHFFFAOYSA-N 0.000 description 2
- KZCSUEYBKAPKNH-UHFFFAOYSA-N 6-aminonaphthalene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KZCSUEYBKAPKNH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
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- 239000004698 Polyethylene Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- VTEBSADXXKSKOE-UHFFFAOYSA-L disodium;4-[[2,4-diamino-5-[[3-[[2,4-diamino-5-[(4-sulfonatophenyl)diazenyl]phenyl]diazenyl]phenyl]diazenyl]phenyl]diazenyl]benzenesulfonate Chemical compound [Na+].[Na+].NC1=CC(N)=C(N=NC=2C=C(C=CC=2)N=NC=2C(=CC(N)=C(N=NC=3C=CC(=CC=3)S([O-])(=O)=O)C=2)N)C=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 VTEBSADXXKSKOE-UHFFFAOYSA-L 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000004584 polyacrylic acid Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 235000021286 stilbenes Nutrition 0.000 description 2
- 239000004575 stone Substances 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 2
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- CYCGXYKRUBKWHT-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)piperazine;dihydrochloride Chemical compound Cl.Cl.ClC1=CC=C(Cl)C(N2CCNCC2)=C1 CYCGXYKRUBKWHT-UHFFFAOYSA-N 0.000 description 1
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- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
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- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 235000019265 sodium DL-malate Nutrition 0.000 description 1
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- KYKFCSHPTAVNJD-UHFFFAOYSA-L sodium adipate Chemical compound [Na+].[Na+].[O-]C(=O)CCCCC([O-])=O KYKFCSHPTAVNJD-UHFFFAOYSA-L 0.000 description 1
- 239000001601 sodium adipate Substances 0.000 description 1
- 235000011049 sodium adipate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 229960001790 sodium citrate Drugs 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 235000019294 sodium fumarate Nutrition 0.000 description 1
- 229940005573 sodium fumarate Drugs 0.000 description 1
- 229940073490 sodium glutamate Drugs 0.000 description 1
- 229940023144 sodium glycolate Drugs 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 239000001394 sodium malate Substances 0.000 description 1
- ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 description 1
- 229940039790 sodium oxalate Drugs 0.000 description 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
- 239000004324 sodium propionate Substances 0.000 description 1
- 235000010334 sodium propionate Nutrition 0.000 description 1
- 229960003212 sodium propionate Drugs 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- 239000001433 sodium tartrate Substances 0.000 description 1
- 229960002167 sodium tartrate Drugs 0.000 description 1
- 235000011004 sodium tartrates Nutrition 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- JEJAMASKDTUEBZ-UHFFFAOYSA-N tris(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OC(Br)(Br)C(C)(C)CBr)OC(Br)(Br)C(C)(C)CBr JEJAMASKDTUEBZ-UHFFFAOYSA-N 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
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- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/38—Trisazo dyes ot the type
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- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/50—Tetrazo dyes
- C09B35/52—Tetrazo dyes of the type
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- 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
- C09B37/00—Azo dyes prepared by coupling the diazotised amine with itself
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- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0072—Preparations with anionic dyes or reactive dyes
- C09B67/0073—Preparations of acid or reactive dyes in liquid form
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
200427784 玖、發明說明： 【發明所屬之技術領域】 本發明係關於一種製備磺化偶氮染料之鹽類之液狀調配 物之方法。 【先前技術】 自染料化學早期階段以來苯胺棕及其偶合産物（例如，cj Duect Brown 44)即爲吾人所知。舉例而言，顏料索引 (Colour Index)顯不，c.I· Direct Brown 44係藉由將 2份磺胺 酸偶合至1份苯胺棕（Bismarck Brown C.I· 21000)上之形式' 而獲得。所引用的德國專利案第468〇4號教示了苯胺棕與磺 胺酸之反應。然而，該産物被大量苯胺棕污染，而苯胺棕 必須藉由過濾去除。染料藉由鹽析自該水溶液中回收。然 而’藉由鹽析獲得之染料因其鹽含量過高而不適於製備液 狀調配物。而且，該等分離步驟成本極大且非常麻煩。 曰本專利案第JP 61 296 069號教示了製備Direct Brown 44之鐘鹽之方法，其自鈉鹽開始，沈澱酸並隨後使用氫氧 化鐘來製備該鐘鹽。 【發明内容】 本發明之一目的係提供一種製備染料之低鹽及低苯胺棕 液狀調配物之方法。而且該方法將具有良好時空産率且産 生極少廢水。 【實施方式】 頃發現’可藉由一種製備磺化偶氮染料之鹽類之液狀調 配物之方法達成此目的，該方法包括：a)由間-苯二胺製備
O:\89\89771.DOC -6- 200427784 苯胺棕；b)於其間未分離苯胺棕之狀況下將至少等莫耳量 之經重氮化之胺基芳基磺酸I偶合至該苯胺棕上： H2N-Ar-S03H (I) 其中Ar爲伸苯基（其可經磺酸基單取代）或萘基（其可經磺 酸基單或雙取代及/或經羥基單取代）；及c)以其酸形式分離 各染料並隨後將其溶於一鹼水溶液中。 可使用之重氮組份I包括胺基芳基磺酸，例如，鄰-、間-及對-胺基本靖酸、1 -胺基本-3，5 -二績酸、1 -胺基苯-2，4 -二 石黃酸、1-胺基苯-2,5-二績酸、1-奈胺-2-績酸、1-秦胺-3-績' 酸、1-奈胺-4 - ^頁酸、1 -奈胺-5 -石頁酸、1 -奈胺-6 -續酸、1 -奈 胺-7-續酸、1-奈胺-8-續酸、1-奈胺-3,6-二項酸、1-秦胺-3，8-一石頁酸、1-奈胺-4,7-二礦酸、1 -胺基-8 -經基奈-4，6 -二續酸、 1-胺基-8-經基奈-4-績酸、1-胺基-8-經基秦-3，6-二績酸、2 _ 胺基奈-1-績酸、2 -奈胺-5-續酸、2 -奈胺-6-續酸、2 -蔡胺- 7-磺酸、2-萘胺-8-磺酸、2-萘胺-1，5-二磺酸、2-萘胺-3,6-二 磺酸、2-萘胺-4,8_二磺酸、2-萘胺-5,7-二磺酸、2-萘胺-6,8-二磺酸、2-萘胺-3,6-二磺酸、2-萘胺-5,7-二磺酸、2-萘胺 -3，6，8 -二♦酸、2 -胺基-8 -經基奈-6 -確酸、2 -胺基-5 -經基奈 -7 -靖酸、2 -胺基-3 -經基奈-6 -績酸及2 -胺基-5 -經基奈-1，7 _ 二續酸。 優先選擇胺基芳基磺酸，其中Ar爲一可經磺酸基取代之 伸苯基或萘基。特別優先選擇鄰-、間-及對-胺基苯磺酸， 尤其是續胺酸（對-胺基苯項酸）。 胺基芳基磺酸I使用習用之重氮化試劑（例如亞硝酸，其
O:\89\89771.DOC 200427784 由驗金屬亞硝酸鹽於酸性條件下形成）重氮化。可使用之重 氮化試劑還包括亞硝基硫酸及亞硝酸烷基酯，尤其是二亞 硝酸新戊二醇酯。 用（例如）胺基績酸去除過量亞硝酸鹽後，將該包含重氮 鹽之反應混合物添加至常用的苯胺棕水溶液中。較佳在介 於4至8之間（且更佳介於5至6之間）之pH值下實施該偶合反 應。 使用熟諳此項技藝者已知之試劑調節該偶合反應之pH 值。可利用之驗包括（例如）驗金屬氫氧化物（例如，氫氧化 納水溶液）、驗金屬碳酸鹽（例如，碳酸鈉、碳酸氫鈉或磷酸 二氫鈉）、胺（例如，乙醇胺）或鹼金屬之羧酸鹽（例如，乙酸 鈉、乙酸鋰、乙酸鉀、甲酸鈉、丙酸鈉、草酸鈉、琥珀酸 納、麵胺酸鈉、己二酸鈉、羥乙酸鈉、乳酸鈉、蘋果酸鈉、 檸檬酸鈉、酒石酸鈉、富馬酸鈉或馬來酸鈉。 了單獨使用重氮組份I或使用其混合物。使用混合物可産 生亦包含不對稱經取代染料之染料混合物。本方法之一較 佳形式係不使用重氮組份之混合物。重氮組份I以二莫耳當 量偶合至苯胺棕上將産生一對稱染料。然而，通常會獲得 包含單、雙、三及四重偶合産物之混合物。 每1莫耳偶合組份所用重氮組份之量較佳介於1至4莫耳 之間，更佳介於1.5至2·5莫耳之間且尤其介於18至2·2莫耳 之間。由此通常可使產物混合物中之苯胺棕含量小於丨〇重 量％。 通常在介於0至2(TC間之溫度下實施該偶合反應。爲完成
O:\89\89771.DOC 200427784 該反應，較佳加熱至使溫度介於2〇至3〇它之間。 根據本發明’續化偶氮染料以其鹽形式分離。此一分離 可於偶合反應完成後藉由酸化該等混合物達成。戲定值 較佳介於0至4.5之間且更佳介於〇至2之間。在本發明方、'去 之一尤佳形式中’逐步降低輝。此可藉由在15至45分鐘 期間分2次或多次添加酸達成。同樣可分多次或甚至連 量來添加酸。 ^ ° 在本方法之另-較佳形式中，使續化偶氮染料酸在介於 20至70 C間之溫度下結晶較爲有利。 ， 由此可以固體形式提供磺化偶氮染料酸，其可由通常習 用之方法(例如)藉由過濾或離心分離。此係_去除偶氮染料 卡：含鹽類之簡單方法。較佳用水洗蘇所獲得染料直至鹽 含量小於5重量％，較佳小於2重量0/〇。 隨後將該磺化偶氮染料溶於稀釋鹼中。所選擇之鹼決定 可獲得的染料之鹽。鈉鹽及/或銨鹽特別佳。 適宜之鹽包括金屬鹽或銨鹽。具體而言，金屬鹽係鋰、 鈉或鉀鹽。對於本發明而言，銨鹽爲含有經取代或未經取 代之銨陽離子之鹽。經取代之銨陽離子之實例爲單烷基_、 一烷基-、二烷基_、四烷基_或节基三烷基_銨陽離子或該些 何生自含氮的五員或六員飽和雜環之陽離子，例如，吡咯 烷鑌陽離子、六氫。比啶鑌陽離子、嗎啉鑌陽離子或派嗪鑌 陽離子或其Ν-單烷基-或Ν，Ν-二烷基-取代產物。本文中之 烷基應理解爲一般意義上之直鏈或支鏈烷基，其可被 一或兩個羥基取代及/或被一至四個醚官能基中之氧原子
O:\89\8977I.DOC 200427784 鹽或其混合 插入。通常，可製備鋰 物
鹽、鈉鹽、鉀鹽或NiL 在本發明方法之一尤佳形式 並在其間未經分離之狀況下使笨胺苯二胺製備苯胺標 染料。 不反應以形成石黃化偶氮 通常，苯胺棕以一習知方法 稽由雙偶虱化1/3之間_茉二脸 並容許剩餘2份偶合之形式來製 表攝為此，將3莫耳間-笨-胺與1.5至2·5莫耳且較佳丨.8至22 、斗Π本一 旲耳之亞硝酸鈉於酸性條 件下反應。較佳選擇其中在一如 在心長知期（例如30至60分鐘且- 較佳爲40至50分鐘)内計量添加酸之方法。爲完成該反應， 需將这反應混合物之ΡΗ值調節至介於心之間，並隨後將 反應混合物授拌一段時間。産生苯胺掠之整個反應可於_5 至+ 25°C之間（且較佳介於〇至说之間）實施。添加完亞硝 酸鹽後，將反應混合物㈣G.U4小時。然後可將胺基芳 基磺酸I之重氮鹽直接計量添加至該反應混合物中。 該石黃化偶li染料之水性鹽溶液可直接用於液狀調配物。 若需要，可將染料溶液與助溶添加劑混合。在此情況下， 其溶液或固體本身皆可與助溶添加劑混合。該等添加劑包 括（例如）水可溶混之有機溶劑，例如，Cl，c4烷醇（例如，曱 醇、乙醇、丙醇、異丙醇、丁醇、異丁醇、第二丁醇或第 三丁醇）、碳醯胺（例如，N，N_二曱基甲醯胺或N，N-二甲基 乙醯胺）、酮或酮醇（例如，丙酮、甲基乙基酮或2-甲基 羥基戊-4-酮）、醚（例如，四氫呋喃或二萼烷）、具有c2_c6 伸烷基單元之單-、募-或聚伸烷基二醇或硫代二醇（例如， O:\89\89771.DOC -10- 200427784 乙二醇、1，2-丙二醇或i，3-丙二醇、丨，2_丁二醇或丨，‘丁 一 醇、新戊二醇、丨，6-己二醇、二乙二醇、三乙二醇、二丙二 醇、硫代二甘醇、聚乙二醇或聚丙二醇）、其他多元醇（例如， 甘油或1，2,6-己三醇）、多元醇iCi_C4烷基醚（例如，乙二醇 單甲醚、乙二醇單乙醚、二乙二醇單甲醚、二乙二醇單 醚、二乙二醇單丁醚（二乙二醇丁醚）或三乙二醇單甲醚或單 乙醚）、多元醇iCrC4烷基酯、r _丁内酯或二甲亞碾。可 使用之助溶添加劑進一步包括内醯胺（例如，己内醯胺卜 吡咯烷酮或N-甲基-2-吡咯烷酮、尿素、環狀尿素（例如，丨，扣 二曱基咪唑烷-2-酮或丨，3-二曱基六氫嘧啶酮）且亦包括 聚丙烯酸、聚丙烯酸衍生物、聚乙烯胺、聚乙烯醯胺、聚 乙酸乙烯酯、聚乙烯醇、聚乙烯基吡咯烷酮、聚矽氧烷或 個別單體之共聚物。同樣，可使用乙亞胺、環氧乙烧或環 氧丙烷之募聚物或該等寡聚物之衍生物。 較佳助溶添加劑爲尿素、單…二_或三乙醇胺、己内醯 胺、具有CrC5伸烷基單元之單…二_或三-伸烷基二醇及/ 或具有伸乙基及/或聚伸乙基單元之寡及聚伸烷基二醇及 其匸广匸4烷基醚及匚广匕烷基酯。極佳者係乙二醇、丨，2-丙二 醇、1,3-丙二醇、新戊二醇、二乙二醇丁醚、烷基聚乙二醇 (MW200-500)、尿素及己内酿胺。 以水性液狀調配物之總量計，較佳液狀調配物主要包含： 1 5 - 3 0重量％之磺化偶氮染料（以無抗衡離子之染料計）； 0-30重量％之助溶添加劑。 特別佳之液狀调配物主要包含1 5重量％至3 〇重量。之石黃 O:\89\8977I.DOC -11 - 200427784 化偶氮染料及1重量％錢重量％(且較佳爲i重量％至5重旦 。物溶添加劑(具體而言，乙二醇、丨，2，二醇、丨，二 、新戊二醇、=乙二醇丁醚、烷基聚乙 W)、尿素及/或己内酿胺）。該等液狀調配物2 在儲存時具有顯著優良之穩定性。該等液狀調配物尤其適 用於纖維素纖維材料（例如，含木材及不含木材之紙張材料 之染色及印染。 根據本發明之方法可提供即可出售之碍化偶氮染料之液 狀調配物’其允許僅藉由用水稀釋來直接製備染浴。該等—_ 液狀調配物之鹽含量較低。使用根據本發明之方法可在4 至5(TC以良好時空産率及高穩定性製備磺化雙偶氮染料之 鹽類之液狀調配物。 下述貫加例係用於闡述本發明。除非另有說明，否則， 份數皆指重量份數。 實例 % 實例1 將173份苯胺棕鹼（vesilvin Base)攪拌加至2500份冰水 中。爲了製備重氮組份，將丨3〇〇份水及157份25重量％之氫 氧化鈉水溶液作爲初始加料引入，然後將1 70份磺胺酸溶於 其中。將1 3 0 0份冰及3 3 5份2 3體積％之亞硝酸納溶液添加至 該磺胺酸溶液中，並添加447份20%之鹽酸以實施重氮化。 再攪拌片刻後，藉由添加胺基磺酸去除過量亞硝酸鹽。 將重氮組份添加至該偶合組份中，然後用氫氧化鈉水溶 液將pH值調節至5.0-6。偶合反應結束後，用鹽酸將pH值調 O:\89\8977l.DOC -12- 200427784 節爲1。過濾固體染料、用水洗務去除鹽分並乾燥。獲得36〇 克去除了 l·5重量％NaCl之染料。笨胺棕之含量占染料之12 重量％。 實例2 將20份根據實例1獲得之染料之濕濾餅與5份丨，2_丙二醇 及72份pH值爲10-12之稀氫氧化鈉水溶液溶解在一起。 經澄清過濾後，將該染料溶液直接用於紙張染色。 對實例3-7之一般試驗說明： 爲了製備偶合組份，需於室溫下將16 3份間笨二胺溶於· 900份水及45份20%之鹽酸中之溶液作爲初始加料引入，添 加1300份冰。然後攪拌添加76份固體亞硝酸鈉。經4〇-5〇分 鐘計量添加395份20%之鹽酸，隨後予以攪拌以完成該反 應。用25重量％之氫氧化鈉水溶液將pH值調節爲3，隨後於 3°C下攪拌1小時。 爲了製備重氮組份，需將1300份水及157份25重量％之氫 氧化納水溶液作爲初始加料引入，並將X份磺胺酸溶於其 中。將1300份冰及γ份亞硝酸鈉溶液（23體積％)添加至該磺 胺酸溶液中，然後添加447份2〇%之鹽酸以實施重氮化。隨 後攪拌片刻，然後藉由添加胺基磺酸去除過量亞硝酸鹽。 將该重氮組份添加至該偶合組份中，並用氫氧化鈉水溶 液將pH值調節至5 〇4。當偶合反應結束後，用鹽酸將pH值 調節爲1並過濾該固體染料、用水洗滌去除鹽並乾燥。 實例3 根據一般試驗說明，使用144份磺胺酸（X)及283份亞硝酸
O:\89\89771.DOC -13 - 200427784 鹽溶液（Y)製備該染料。獲得332克除去了 0.84重量％NaCl 之染料。笨胺棕之含量占該染料之丨5重量％。 實例4 根據一般試驗說明，使用170份磺胺酸（X)及3 35份亞硝酸 鹽溶液（Y)製備該染料。獲得35〇克除去了 〇·46重量％NaCl 之染料。苯胺棕之含量占該染料之12重量％。 實例5 根據一般試驗說明，使用183份磺胺酸（X)及361份亞硝酸 鹽溶液（Y)製備該染料。獲得39〇克除去了 1.3重量 染料。苯胺棕之含量占該染料之1 〇重量〇/〇。 實例6 根據一般試驗說明，使用170份磺胺酸（χ)及344份亞硝酸 鹽溶液（Y)製備該染料。獲得347克除去了 1.3重量％1^化1之 染料。苯胺棕之含量占該染料之6.8重量％。 實例7 根據一般試驗說明，使用177份磺胺酸（χ)及357份亞硝酸 鹽溶液（Υ)製備該染料。獲得352克除去了 〇16重量％1^化1 之染料。苯胺棕之含量占該染料之58重量％。 實例8 將20伤根據實例3-7獲得之染料之濕濾餅與5份丨，2•丙二 醇及75份pH值爲1(Μ2之稀氫氧化鈉水溶液溶解在一起。經 澄清過濾後’將該染料溶液直接用於紙張染色。 實例9 將20份根據實例3-7獲得之染料之濕濾餅與5份丨，2_丙二 O:\89\89771.DOC -14- 200427784 醇及75份pH值爲9-10之稀氫氧化鈉水溶液溶解在—起。、與 澄清過濾後，將該染料溶液直接用於紙張染色。 實例10 將23份（視爲100%)根據實例3-7獲得之染料之濕渡餅與5 份新戊一醇一起浴於72伤pH值爲9-1 〇之稀氫氧化鈉水溶液 與25%氨之混合物（此可獲得1/1之鈉/銨鹽形式）中。經澄清 過濾後，將該染料溶液直接用於紙張染色。 實例11 將23份（視爲100%)根據實例3-7獲得之染料之濕液餅與十 份乙基聚乙二醇（MW 400)—起溶於76份pH值爲9-1〇之稀氯 氧化鈉水溶液與25%氨之混合物（此可獲得ι/丨之納/銨鹽形 式）中。經澄清過濾後，將該染料溶液直接用於紙張染色。 實例12 將2 1份（視爲10 0 % )根據實例3 - 7獲得之染料之濕漁餅與5 份乙基聚乙一醇（MW 200)—起溶解於74份pH值爲9-10之稀 氫氧化鈉水溶液與25%之氨之混合物（此可獲得ι/丨之納/鐘 鹽形式）中。經澄清過濾後，將該染料溶液直接用於紙張染 色。 實例13 將23份（視爲100%)根據實例3 -7獲得之染料之濕濾餅與 2.5份尿素一起溶解於74.5份pH值爲9-1〇之稀氫氧化鈉水溶 液與2 5 %氨之混合物（此可獲得1 /1之納/銨鹽形式）中。經澄 清過濾後，將該染料溶液直接用於紙張染色。 O:\89\89771.DOC -15-
Claims (1)
- 200427784 拾、申請專利範圍： 1· 一種製備磺化偶氮染料之鹽類之液狀調配物之方法，該 方法包括：a)由間-苯二胺製備苯胺棕；b)於其間未分離 苯胺棕之狀況將至少等莫耳量之經重氮化的胺基芳基磺 酸I偶合至笨胺棕上： H2N-Ar-S03H ⑴ 其中Ar爲伸苯基（其可經磺酸基單取代）或萘基（其可經 磺酸基單或雙取代及/或經羥基單取代）；及c)以其酸形式 分離該等染料並隨後將其溶於一鹼水溶液中。 一 2·如申請專利範圍第㈣之方法，其中該等偶氮染料係由鄰 -、間-及/或對-胺基苯續酸重氮組份製備。 3 士申明專利範圍第1或2項之方法，其中所用苯胺棕與重 氮組份之化學計量比介於1:1至Π4之間。 4.::申請專利範圍第销2項之方法，#中該等偶氮染料係 藉由將pH值調節至介於〇至4·5間之值予以分離。 5·如中請專利範圍第⑷項之方法，其中該等偶氮染料係 藉由逐步酸化而結晶。 6. 如申請專利範圍第15戈2項之方法，其中該等項化偶氮毕 料係於20至70t下以其酸形式結晶。 、 7. -種根射請專利範圍第丨或2項獲得之液狀調配物，其 包括選自由以下組成之群之助溶添加劑··尿素、單_、一 或三·乙醇胺、己内醯胺、具有CrC5伸烷基單元之單·、 二-或三-伸烷基二醇及具有伸乙基及/或伸丙基單元之募_ 及聚-伸炫基一醇及其Ci-C4烧基鱗及匕-匕燒基酯。 O:\89\89771.DOC 200427784 8.如申請專利範圍第7項之液狀調配物，其含有占無抗衡離 子之染料之1 5重量％至30重量％間之磺化偶氮染料及占 該水性液狀調配物之總量之0重量％至30重量％間之助溶 添加劑。 O:\89\89771.DOC 200427784 柒、指定代表圖： (一) 本案指定代表圖為：（無）。 (二) 本代表圖之元件代表符號簡單說明： 捌、本案若有化學式時，請揭示最能顯示發明特徵的化學式： (無） O:\89\89771.DOC
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| US2002606A (en) * | 1932-06-03 | 1935-05-28 | Herman H Kistner | Piston |
| US2022606A (en) | 1934-06-08 | 1935-11-26 | Du Pont | Brown disazo dyes |
| DE3011235A1 (de) | 1980-03-22 | 1981-10-01 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von fluessigeinstellungen basischer azofarbstoffe |
| DE3025557A1 (de) | 1980-07-05 | 1982-02-04 | Bayer Ag, 5090 Leverkusen | Loesung kationischer polyazofarbstoffe |
| EP0169808A3 (en) | 1984-07-24 | 1988-12-21 | Ciba-Geigy Ag | Uv-absorber compounds, method for their preparation and their use as image dyes in photographic materials for the silver dye-bleaching process |
| JPH07748B2 (ja) | 1985-06-25 | 1995-01-11 | 株式会社日本化学工業所 | 水性濃厚染料溶液組成物 |
| US4952680A (en) * | 1987-04-23 | 1990-08-28 | Basf Aktiengesellschaft | Preparation of stable solutions of azo dyes of m-phenylenediamine by reaction with formic acid |
-
2003
- 2003-11-17 EP EP03779941A patent/EP1567598B1/de not_active Expired - Lifetime
- 2003-11-17 WO PCT/EP2003/012803 patent/WO2004048478A1/de active IP Right Grant
- 2003-11-17 ES ES03779941T patent/ES2276137T3/es not_active Expired - Lifetime
- 2003-11-17 AU AU2003288074A patent/AU2003288074A1/en not_active Abandoned
- 2003-11-17 JP JP2004554358A patent/JP2006508209A/ja active Pending
- 2003-11-17 CN CNB2003801044469A patent/CN100345910C/zh not_active Expired - Fee Related
- 2003-11-17 DE DE50305713T patent/DE50305713D1/de not_active Expired - Lifetime
- 2003-11-17 AT AT03779941T patent/ATE345369T1/de active
- 2003-11-17 US US10/534,057 patent/US7488810B2/en not_active Expired - Fee Related
- 2003-11-28 TW TW092133584A patent/TW200427784A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2276137T3 (es) | 2007-06-16 |
| EP1567598B1 (de) | 2006-11-15 |
| JP2006508209A (ja) | 2006-03-09 |
| WO2004048478A1 (de) | 2004-06-10 |
| DE50305713D1 (de) | 2006-12-28 |
| EP1567598A1 (de) | 2005-08-31 |
| US7488810B2 (en) | 2009-02-10 |
| CN1717454A (zh) | 2006-01-04 |
| CN100345910C (zh) | 2007-10-31 |
| US20060052590A1 (en) | 2006-03-09 |
| AU2003288074A1 (en) | 2004-06-18 |
| ATE345369T1 (de) | 2006-12-15 |
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