CN1070894C - 偶氮染料及其制备方法和应用 - Google Patents
偶氮染料及其制备方法和应用 Download PDFInfo
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- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title description 5
- 239000000987 azo dye Substances 0.000 title 1
- 239000000975 dye Substances 0.000 claims abstract description 44
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- 238000004043 dyeing Methods 0.000 claims abstract description 10
- 239000000463 material Substances 0.000 claims abstract description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 2
- -1 Phenyl Chemical group 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 238000006193 diazotization reaction Methods 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 4
- 239000002657 fibrous material Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 239000000835 fiber Substances 0.000 abstract description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 210000002268 wool Anatomy 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 4
- 239000012346 acetyl chloride Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 230000008878 coupling Effects 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 235000011167 hydrochloric acid Nutrition 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- PPVRMPPLECDING-UHFFFAOYSA-N 4-[(4-aminophenyl)diazenyl]benzenesulfonic acid Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 PPVRMPPLECDING-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical class COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
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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
- 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
- C09B31/04—Disazo dyes from a coupling component "C" containing a directive amino group
- C09B31/043—Amino-benzenes
- C09B31/047—Amino-benzenes containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof
-
- 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
- C09B43/128—Aliphatic, cycloaliphatic or araliphatic acids
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/924—Polyamide fiber
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Abstract
下式的偶氮染料
其中各基团如说明书中定义。该偶氮染料对含氮或羟基的纤维材料产生有良好牢度的染色。
Description
本发明涉及新型的偶氮染料、它们的制备方法以及在纤维材料特别是纺织纤维材料印染中的应用。
式中,R1和R2各自独立为未取代的或被羟基、C1-C4烷氧基或卤素取代的C1-C4烷基或C1-C4烷氧基;未取代的或被C1-C4烷基、C1-C4烷氧基或卤素取代的苯基或苯氧基;或者式-N(R3)R4的基团,其中R3和R4各自独立为氢、C1-C4烷基或C2-C4烷酰基(未取代的或在烷基部分被羟基或C1-C4烷氧基取代的),条件是R1和R2不同时为甲基。
C1-C4烷基R1、R2、R3和R4各自独立为甲基、乙基、丙基、异丙基、丁基、仲丁基、叔丁基或异丁基,特别是甲基或乙基。C1-C4烷基R1和R2可进一步被羟基、卤素(如溴或特别是氯)或特别是C1-C4烷氧基(如乙氧基或优选甲氧基)取代。甲氧基甲基可作为相应的取代基的例子。
C1-C4烷氧基R1和R2各自独立为如甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基或异丁氧基,特别是甲氧基或优选乙氧基。C1-C4烷氧基R1和R2可进一步被羟基、卤素(如溴或优选氯)或特别是被C1-C4烷氧基(如甲氧基或乙氧基)取代。相应的未取代的基团是优选的。
C2-C4烷酰基R3和R4各自独立为如丙酰基或特别是乙酰基。C2-C4烷酰基R3和R4可进一步被羟基或特别是C1-C4烷氧基(如甲氧基或乙氧基)取代。优选的是,这些基团进一步被C1-C4烷氧基,特别是甲氧基取代。在这里甲氧乙酰基是特别优选的。
苯基或苯氧基R1和R2除相应的未取代基团外,为被C1-C4烷基(如甲基、乙基、丙基、异丙基、丁基、仲丁基、叔丁基或异丁基)、C1-C4烷氧基(如甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基或异丁氧基)或被卤素(如氟、溴或特别是氯)取代的基团。在这里相应的苯基是优选的。
R3优选为氢或C1-C4烷基,特别是氢。
R4优选为氢、C1-C4烷基、或C2-C4烷酰基(未取代的或在烷基部分被C1-C4烷氧基取代的),特别是氢或烷基部分被C1-C4烷氧基取代的C2-C4烷酰基。R4特别优选为氢或甲氧乙酰基,特别是氢。
R3和R4特别优选为氢。
R1优选为未取代的或被羟基、C1-C4烷氧基或卤素取代的C1-C4烷基或C1-C4烷氧基,或者式-N(R3)R4的基团,其中R3和R4为如上规定和优选的。优选的是,在这一情况下,R3为氢和R4为氢或C2-C4烷酰基(在烷基部分还可被C1-C4烷酰基取代),特别是氢。
R1优选为C1-C4烷酰基;未取代的或被C1-C4烷氧基取代的C1-C4烷基;或式-N(R3)R4的基团,其中R3和R4为如上规定和优选的。优选的是,在这种情况下,R3为氢和R4为氢或C2-C4烷酰基(在烷基部分还可被C1-C4烷氧基取代),特别是氢。
R1特别优选为甲基;乙基;甲氧基;乙氧基;甲氧基或乙氧基取代的甲基;或氨基。
R1尤其优选为甲基;乙基;乙氧基;甲氧基取代的甲基;或氨基。R1优选为甲基;乙基;乙氧基或甲氧基取代的甲基,特别是甲基。
R2为如上R1优选的,乙基是特别优选的。
优选的是,R1和R2各自独立为未取代的或被羟基、C1-C4烷氧基或卤素取代的C1-C4烷基或C1-C4烷氧基;或式-N(R3)R4基团,其中R3为氢和R4为氢或C2-C4烷酰基(在烷基部分还可被C1-C4烷氧基取代),特别是氢。
优选的是,R1和R2各自独立为C1-C4烷氧基;未取代的或被C1-C4烷氧基取代的C1-C4烷基;或氨基。
R1和R2特别优选各自独立为甲基;乙基;甲氧基;乙氧基;被甲氧基或乙氧基取代的甲基;或氨基。
R1和R2特别优选各自独立为甲基;乙基;乙氧基;被甲氧基取代的甲基;或氨基,特别是甲基;乙基;乙氧基;或被甲氧基取代的甲基。
特别有意义的式(1)的偶氮染料是R1为甲基和R2为乙基的偶氮染料。
在式(1)的偶氮染料中磺基优选键联在相对于偶氮基的对位上。
式中,R1和R2为如式(1)规定的。
式(2)化合物的重氮化按本身已知的方法进行,例如用亚硝酸盐(如碱金属亚硝酸盐,如亚硝酸钠),在矿物酸介质中(如在盐酸介质中),在-5-40℃(优选0-10℃)下进行。
生成式(3)偶联组分的偶联按本身已知的方法在酸性、中性或弱碱性pH值(如pH值为3-7)和-5-30℃(优选0-25℃)下进行。
式中,Hal为卤素如氯、溴或碘,特别是氯。式(5)化合物的例子是乙酰氯、丙酰氯、甲氧乙酰氯和氯甲酸乙酯。引入式(4)基团的化合物另外的一些例子是乙酸酐和丙酸酐。
上述式(4)基团的引入例如可在偶极非质子传递溶剂(如二甲基甲酰胺或二甲基亚砜)中,或在水中或优选在吡啶中,在10-80℃(特别是在10-50℃)下进行。
在本发明制备式(1)的偶氮染料的方法中,式(2)、(3)、(4)和(5)化合物的取代基为上述优选的。
式(2)、(3)和(5)的化合物是已知的或可类似已知化合物制备。
式(1)的偶氮染料可为游离酸的形式,优选为其盐的形式。
盐例如为碱金属盐或胺盐或有机胺的盐。
例子是钠盐、锂盐、钾盐或胺盐或一乙醇胺的盐、二乙醇胺的盐或三乙醇胺的盐。
本发明式(1)的偶氮染料适合用已知的方法印染特别是含氮或羟基的纤维材料,如纤维素、丝,特别是羊毛和合成聚酰胺的织物纤维材料。优选印染天然的或合成的聚酰胺纤维材料。本发明式(1)的偶氮染料如果预先适当制备的话,可以一般常规的形式用于印染。可得到有良好的全面性能,特别是良好的摩擦牢度、湿加工牢度、湿摩擦牢度和光牢度的匀染。此外,本发明的偶氮染料是易水溶性的,可易于与其他染料组合使用。上述织物材料可为各种的加工形式,如纤维、纱、机织织物或针织织物。
在以下的实施例中,份数为份重。温度为摄氏度。份重与份体积有克与立方厘米相同的关系。
实施例1
将22.2份4-氨基偶氮苯-4’-磺酸在75℃下溶于400份水中,然后加入20份4N亚硝酸钠溶液。将溶液在0-5℃下,在20min内滴加到400份冰和20份浓盐酸中。将如此得到的褐色悬浮液搅拌1hr,然后用碳酸钠溶液(10%)将pH值调节到4。然后在0-5℃下,在60min内将重氮悬浮液滴加到含有150份盐酸3-氨基苯基脲于400份水和63.5份1N氢氧化钠溶液的偶联溶液中。在偶联过程中,pH值保持在5。在0-5℃2hr,然后在室温下过夜使混合物反应完全。过滤褐色悬浮液,并用水洗涤残留物。将潮湿的残留物与1000份水一起搅拌,用67份1N氢氧化钠溶液将pH值调节到8。在60℃下加入70份氯化钠,在50℃下过滤细的悬浮液。干燥后得到游离酸形式的化合物,相应于下式的化合物,
实施例2-4
实施例5
将6.6份式(104)的化合物搅拌在150份吡啶中,然后在10min内将5.9份乙酰氯滴加入,温度升到45℃。接着将反应混合物搅拌1hr,然后加入50份甲醇。将橙色悬浮液倒入750份浓氯化钠水溶液中,然后过滤,用5%氯化钠水溶液和用甲醇洗涤残留物。干燥后,得到游离酸形式的染料,相应于下式的化合物。式(105)的染料使羊毛和聚酰胺染色成橙色。
实施例6-14
重复实施例5的步骤,但使用等摩尔量式(101)、(102)和(103)化合物中的一种化合物代替6.6份式(104)的化合物,等摩尔量丙酰氯或甲氧乙酰氯代替5.9份乙酰氯。得到游离酸形式的下式染料。 式(106)-(114)的染料使羊毛和聚酰胺染色成橙色。
实施例15
重复实施例5的步骤,但使用等摩尔量的式(10)化合物代替6.6份式(104)化合物和等摩尔量甲氧乙酰氯代替5.9份乙酰氯。得到游离酸形式染料,相应于下式的化合物。式(15)的染料使羊毛和聚酰胺染色成橙色。
实施例16
在80℃下,将4.4份式(102)的化合物搅拌在50份吡啶中。然后在25℃下,在10min内将6.5份氯甲酸乙酯滴加入,在这一过程中,温度升至42℃。随后将混合物在这一温度下搅拌1hr,然后在室温下将75份甲醇和25份25%氯化钠水溶液加到反应混合物中。过滤悬浮液,用10%氯化钠水溶液,然后用甲醇洗涤残留物。然后湿残留物从醇和水的混合物(1∶1)中重结晶。干燥后,得到2.8份游离酸形式的染料,相应于下式的化合物式(116)的染料使羊毛和聚酰胺染色成橙色。
实施例17-19
式(117)、(118)和(119)的染料使羊毛和聚酰胺染色成橙色。
实施例20
在室温下,将4.4份式(102)的化合物搅拌在70份水中,然后加入3份三乙胺和10份丙酮。在10min内,将5.7份氯甲酸甲酯滴加到橙色溶液中,在这一过程中温度升至32℃。通过加入1N氢氧化钠水溶液使pH值保持在7。加入20份丙酮后,将混合物搅拌30min,然后加入50份甲醇。将混合物搅拌20min,过滤出产物,依次用40份5%氯化钠溶液、50份乙醇和20份甲醇洗涤。干燥后,得到4份相应于下式的游离酸形式的染料。式(120)的染使羊毛和聚酰胺染色成橙色。
实施例21和22
重复实施例20的步骤,但用等摩尔量式(101)和(104)化合物中的一种化合物代替4.4份式(102)的化合物。得到下式的游离酸形式的染料。
式(121)和(122)的染料使羊毛和聚酰胺染色成橙色。
染色实施例:
在室温下,将1份匀染助剂(高级脂族胺与环氧乙烷的缩合产物)加到2000份去矿物水中。然后用乙酸使染缸pH值达到6。加入0.5份实施例5的式(105)染料。将100份尼龙-6,6纤维材料(Helancatricot)放入得到的染料溶液中,在45min内将染缸温度加热到约96℃。将此温度保持45-60min,然后将染缸冷却到70℃,取出染色的织物,用水清洗,然后干燥。得到有橙色光泽的染色纤维。
Claims (14)
2.根据权利要求1的偶氮染料,其中R3为氢。
3.根据权利要求1和2的偶氮染料,其中R4为氢或的烷基部分被C1-C4烷氧基取代C2-C4烷酰基。
4.根据权利要求1和2中任一项的偶氮染料,其中R3和R4为氢。
5.根据权利要求1和2中任一项的偶氮染料,其中R1和R2各自独立为未取代的或被羟基、C1-C4烷氧基或卤素取代的C1-C4烷基或C1-C4烷氧基;或式-N(R3)R4的基团,其中R3和R4为氢,或的烷基部分被C1-C4烷氧基取代C2-C4烷酰基。
6.根据权利要求1和2中任一项的偶氮染料,其中R1和R2各自独立为C1-C4烷氧基;未取代的或被C1-C4烷氧基取代的C1-C4烷基;或氨基。
7.根据权利要求1和2中任一项的偶氮染料,其中R1和R2各自独立为甲基;乙基;甲氧基;乙氧基;被甲氧基或乙氧基取代的甲基;或氨基。
8.根据权利要求1和2中任一项的偶氮染料,其中R1和R2各自独立为甲基;乙基;乙氧基;被甲氧基取代的甲基;或氨基。
9.根据权利要求1和2中任一项的偶氮染料,其中R1和R2各自独立为甲基;乙基;乙氧基;或被甲氧基取代的甲基。
10.根据权利要求1和2中任一项的偶氮染料,其中R1为甲基和R2为乙基。
11.根据权利要求1和2中任一项的偶氮染料,其中式(1)的偶氮染料中的磺基键联在相对于偶氮基的对位上。
13.根据权利要求1-11中任一项的偶氮染料应用于含有氮或羟基的纤维材料印染的用途。
14.根据权利要求13的用途,用于天然的或合成的聚酰胺纤维材料的印染。
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EP (1) | EP0754732B1 (zh) |
JP (1) | JPH0931347A (zh) |
KR (1) | KR970006409A (zh) |
CN (1) | CN1070894C (zh) |
CA (1) | CA2181663A1 (zh) |
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TW (1) | TW415960B (zh) |
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US5948125A (en) * | 1997-05-20 | 1999-09-07 | Ciba Specialty Chemicals Corporation | Method of treating dyed, natural or synthetic polyamide fibre materials |
US20110254661A1 (en) | 2005-12-23 | 2011-10-20 | Invue Security Products Inc. | Programmable security system and method for protecting merchandise |
PT2016135E (pt) * | 2006-04-07 | 2009-08-17 | Clariant Finance Bvi Ltd | Corantes ácidos |
CN104812191B (zh) | 2014-01-29 | 2018-03-09 | 纬创资通股份有限公司 | 具有防盗功能的背盖及具有防盗功能的显示屏幕 |
CN104710322B (zh) * | 2015-02-27 | 2017-04-12 | 宜兴市中正化工有限公司 | 一种红玉酯化液的合成方法 |
TWI667293B (zh) * | 2015-03-16 | 2019-08-01 | 瑞士商亞齊羅馬Ip公司 | 三偶氮酸性染料及其製造方法與用途、以及將其用於染色或印刷基板的製程和使用其所得到之具有顏色的基板、以及其染色組成 |
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CH333517A (de) * | 1954-08-25 | 1958-10-31 | Bayer Ag | Verfahren zur Herstellung von Tetrakisazofarbstoffen |
FR1198990A (fr) * | 1957-03-07 | 1959-12-10 | Ciba Geigy | Nouveaux colorants azoïques, leur préparation et leur utilisation |
US3040024A (en) * | 1957-03-07 | 1962-06-19 | Ciba Ltd | Azo-dyestuffs |
DE2708779C2 (de) * | 1977-03-01 | 1985-09-05 | Bayer Ag, 5090 Leverkusen | Disazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
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- 1996-07-12 EP EP96810457A patent/EP0754732B1/de not_active Expired - Lifetime
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- 1996-07-19 CA CA002181663A patent/CA2181663A1/en not_active Abandoned
- 1996-07-19 CN CN96110678A patent/CN1070894C/zh not_active Expired - Fee Related
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EP0754732B1 (de) | 2001-08-16 |
CN1145933A (zh) | 1997-03-26 |
US5691459A (en) | 1997-11-25 |
CA2181663A1 (en) | 1997-01-22 |
EP0754732A1 (de) | 1997-01-22 |
KR970006409A (ko) | 1997-02-19 |
JPH0931347A (ja) | 1997-02-04 |
TW415960B (en) | 2000-12-21 |
DE59607487D1 (de) | 2001-09-20 |
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