CN1193331A - 酸性偶氮染料 - Google Patents
酸性偶氮染料 Download PDFInfo
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- 239000000975 dye Substances 0.000 title claims abstract description 45
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title abstract description 6
- 239000002253 acid Substances 0.000 title description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims abstract description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- -1 hydroxysulphonyl Chemical group 0.000 abstract description 20
- 238000004043 dyeing Methods 0.000 abstract description 5
- 239000000758 substrate Substances 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000010168 coupling process Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 230000008878 coupling Effects 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000010985 leather Substances 0.000 description 7
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 239000002932 luster Substances 0.000 description 4
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 4
- 210000002268 wool Anatomy 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 239000000987 azo dye Substances 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
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical group 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- XIFJZJPMHNUGRA-UHFFFAOYSA-N n-methyl-4-nitroaniline Chemical compound CNC1=CC=C([N+]([O-])=O)C=C1 XIFJZJPMHNUGRA-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000004753 textile 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/08—Disazo dyes in which the coupling component is a hydroxy-amino compound
- C09B33/10—Disazo dyes in which the coupling component is a hydroxy-amino compound in which the coupling component is an amino naphthol
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
右式的偶氮染料适用于天然物质或合成物质染色,式中,环A可为苯稠合的环,X为氢或C1-C4烷基,R1为氢、C1-C4烷基,卤素、羧基、C1-C4烷氧基羰基或羟基磺酰基,R2为氢、C1-C4烷基、卤素、羧基或C1-C4烷氧基羰基,或者R1和R2一起为式L-NZ-CO的基团,其中L为亚甲基或羰基,Z为取代的或未取代的C1-C4烷基,或者取代的或未取代的苯基,R3为氢、C1-C4烷基、羟基、C1-C4烷氧基、苯氧基、C1-C4烷酰氧基或苯甲酰氧基。
Description
本发明涉及式I的新型偶氮染料式中,环A可为苯并稠环,
X为氢或C1-C4烷基,
R1为氢,C1-C4烷基、卤素、羧基、C1-C4烷氧基羰基或羟基磺酰基,
R2为氢、C1-C4烷基、卤素、羧基或C1-C4烷氧基羰基,或者R1和R2一起为式L-NZ-CO基团,其中L为亚甲基或羰基,Z为有C1-C4烷氧基取代的或没有C1-C4烷氧基取代的C1-C4烷基,或者未取代的苯基或C1-C4烷基取代的或C1-C4烷氧基取代的苯基,以及
R3为氢、C1-C4烷基、羟基、C1-C4烷氧基、苯氧基、C1-C4烷酰氧基或苯甲酰氧基;以及还涉及这些染料用于天然物质或合成基质染色的应用。
本发明的一个目的是提供具有各种有利的应用性能的新型偶氮类酸性染料。
我们已发现,这一目的可通过上述规定的式I偶氮染料来达到。
在上式I中出现的任何烷基可为直链的或支链的。
R1、R2、R3、X和Z例如各自为甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基或叔丁基。
R1和R2例如也可各自为氟、氯、溴、甲氧基羰基、乙氧基羰基、丙氧基羰基、异丙氧基羰基或丁氧基羰基。
Z例如也可为2-甲氧基乙基、2-乙氧基乙基、2-丙氧基乙基、2-异丙氧基乙基、2-丁氧基乙基、2-或3-甲氧基丙基、2-或3-乙氧基丙基、2-或3-丙氧基丁基、2-或3-丁氧基丙基、2-或4-甲氧基丁基、2-或4-乙氧基丁基、2-或4-丙氧基丁基、2-或4-丁氧基丁基、苯基、2-、3-或4-甲基苯基、2,4-二甲基苯基、2-、3-或4-甲氧基苯基或2,4-二甲氧基苯基。
R3例如也可为甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、异丁氧基、仲丁氧基、甲酰氧基、乙酰氧基、丙酰氧基、丁酰氧基或异丁酰氧基。
因为式I的偶氮染料含有许多羟基磺酰基,所以本发明也涉及它们的盐。
在这里适合的盐为金属盐或铵盐。金属盐特别是锂盐、钠盐或钾盐。对于本发明来说,铵盐指含有未取代的铵阳离子或取代的铵阳离子的盐。取代的铵阳离子的例子是单烷基-、二烷基-、三烷基-、四烷基-或苄基三烷基-铵阳离子,铵阳离子由五元环或六元环饱和的含氮杂环化合物得到,如吡咯烷鎓阳离子、哌啶鎓阳离子、吗啉鎓阳离子或哌嗪鎓阳离子,或其N-单烷基-或N,N-二烷基-取代的产物。在这里烷基通常指直链的或支链的C1-C20烷基,它可被1或2个羟基取代和/或被1至4个醚官能度中的氧原子间隔。
式Ia的偶氮染料是优选的式中,环A、X、R1、R2和R3各自为如上规定的。
式Ib的偶氮染料也是优选的式中,环A、X、R1、R2和R3各自为如上规定的。
这样的式I偶氮染料也是优选的,其中R1为氢、甲基、羧基、C1-或C2-烷氧基羰基或羟基磺酰基。
这样的式I偶氮染料也是优选的,其中R2为氢、甲基、羧基或C1-或C2-烷氧基羰基。
这样的式I偶氮染料也是优选的,其中R3为氢或羟基。
这样的式I偶氮染料也是优选的,其中环A不是苯并稠环的。
这样的式I偶氮染料也是优选的,其中R1、R2和R3中至少一个不是氢。
这样的式I偶氮染料也是优选的,其中X为氢。
这样的式I偶氮染料是特别优选的,其中R2为羟基。
这样的式I偶氮染料是特别优选的,其中R1和R2都为氢,R3为羟基。
可特别挑选出具有特别技术意义的式Ic的偶氮染料以及式Id的染料。式I的新型偶氮染料可用已知的方法来制得。例如,首先使硝基苯胺偶氮化,然后使生成的偶氮盐与1-羟基-8-氨基萘-3,6-二磺酸或1-羟基-8-氨基萘-4,6-二磺酸偶联。
然后,生成的式II单偶氮染料也可用已知的方法与这样一种偶氮盐偶联,以制得式I的偶氮染料;该偶氮盐可通过式III磺酰基化合物常规的偶氮作用来制备式中,环A、R1、R2、R3和X各为如上规定的。
式I新型的偶氮染料很适合用于天然物质或合成物质如羊毛、皮革或聚酰胺染色。它们特别适合皮革染色。
得到的染色有淡绿色至淡红蓝色色泽,以及有良好的泳移牢度和湿牢度性质。
新型染料不仅可单独使用,而且也可相互混合使用或与其他染料混合使用。
新型染料还适用于喷墨法(纸和纺织品)。
以下的实施例用来说明本发明。
实施例1
在45-50℃下,将42克下式的偶氮组分在90毫升浓度18.5%(重量)的盐酸中搅拌2小时。然后用冰将混合物冷却到0℃,并在5分钟内滴加入47毫升浓度23%(重量)的亚硝酸钠水溶液;在此过程中将温度保持在最高5℃。随后将混合物搅拌1小时,分解过量的亚硝酸,然后加入70.2克下式的偶联组分。用冰冷却的氢氧化钠稀溶液将混合物的pH值调节到9.5-10。然后用碳酸钠中和偶联过程游离出的酸。将混合物在pH值9-10下搅拌过夜。然后将混合物加热到70-75℃,将pH值调节到6,并用氯化钠使染料沉淀。
用常规的方法分离,干燥并研磨,得到133克黑色粉末,它在水中呈蓝色溶液。在pH值约为4下,溶液的UV-VIS谱在605纳米处有最大值。该染料有下式结构,对皮革、羊毛和聚酰胺的亲合性极好。
实施例2
将57克下式的偶氮组分在150毫升浓度18.5%(重量)的盐酸中搅拌过夜。然后用冰将混合物冷却到0℃,并在30分钟内将48毫升浓度为23%(重量)的亚硝酸钠水溶液滴加入。随后将混合物在0-5℃下搅拌2小时,使过量的亚硝酸分解,加入70.2克实施例1提到的偶联组分。用冰冷却的氢氧化钠稀溶液将偶联混合物的pH值升至7,随后将混合物在此pH值下搅拌30分钟,用碳酸钠将pH值调节到8-8.5,并将混合物搅拌过夜。此后将混合物加热到70℃,然后在此温度下搅拌1小时,并与浓盐酸混合,使下式的染料沉淀,并趁热过滤出来。
经干燥和研磨得到150克黑色粉末。在中性条件下,该粉末在水中呈深蓝色溶液;在pH值约为4下,该水溶液的UV-VIS谱在608纳米处有最大值。
染料使羊毛染色成藏青色色泽,有良好的耐光牢度。皮革染色工艺的染色母液被尽染;皮革被染色成深蓝色色泽。
实施例3
将44.5克下式的偶氮组分与150毫升浓度为18.5%(重量)盐酸一起搅拌,并用150毫升冷水稀释。然后将混合物冷却到0℃,并在30分钟内滴加入48毫升浓度为23%(重量)的亚硝酸钠水溶液。将混合物在0-5℃下搅拌2.5小时,分解过量的亚硝酸,然后加入70.2克实施例1提到的偶联组分。用冰冷却的氢氧化钠稀溶液将混合物的pH值调节到7。随后用碳酸钠将pH值升至8-8.5,并将混合物搅拌过夜。此后,将混合物加热至75℃;用盐酸酸化的方法使染料沉淀,并用吸滤法趁热过滤出。
经干燥和研磨得到130克黑色粉末,它使羊毛和聚酰胺染色成藏青色色泽。将皮革染色成深蓝色,有良好的泳移牢度。
羊毛上的染色有极好的耐光牢度。在pH值约4下,该染料在水中的UV-VIS谱在603纳米处有最大值。该染料有下式
实施例4
将40克下式的偶氮组分用类似实施例1的方法偶氮化。将生成的偶氮盐悬浮液与70.2克实施例1提到的偶联组分混合,后者已溶于pH值为7.5的水中。用碳酸钠将偶联混合物的pH值调节至7.5。将混合物搅拌1小时,随后将pH值调节至9-10。此后将它酸化到pH值4。
用吸滤法过滤出下式的沉淀染料,
经干燥和研磨,得到145克黑色粉末。该染料含有约8%(重量)氯化钠。它使皮革染色成蓝色光泽,有良好的泳移牢度。在pH值为4下,水溶液的UV-VIS光谱在597纳米处有最大值。
Claims (10)
3.根据权利要求1的偶氮染料,其中偶氮染料有式Ib,式中,环A、X、R1、R2和R3各为权利要求1中规定的。
4.根据权利要求1的偶氮染料,其中R1为氢、甲基、羧基、C1-或C2-烷氧基羰基或羟基磺酰基。
5.根据权利要求1的偶氮染料,其中R2为氢、甲基、羧基或C1-或C2-烷氧基羰基。
6.根据权利要求1的偶氮染料,其中R3为氢或羟基。
7.根据权利要求1的偶氮染料,其中环A不为苯稠合的环。
8.根据权利要求1的偶氮染料,其中R1、R2和R3中至少一个不为氢。
9.根据权利要求1的偶氮染料,其中X为氢。
10.权利要求1的偶氮染料用于天然物质或合成物质染色的应用。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19530176A DE19530176A1 (de) | 1995-08-17 | 1995-08-17 | Saure Diazofarbstoffe |
DE19530176.5 | 1995-08-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1193331A true CN1193331A (zh) | 1998-09-16 |
Family
ID=7769657
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN96196331A Pending CN1193331A (zh) | 1995-08-17 | 1996-08-05 | 酸性偶氮染料 |
Country Status (7)
Country | Link |
---|---|
US (1) | US5834602A (zh) |
EP (1) | EP0850279A1 (zh) |
JP (1) | JPH11511189A (zh) |
CN (1) | CN1193331A (zh) |
AR (1) | AR003252A1 (zh) |
DE (1) | DE19530176A1 (zh) |
WO (1) | WO1997007168A1 (zh) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0877775A2 (de) * | 1996-01-25 | 1998-11-18 | Basf Aktiengesellschaft | Saure disazofarbstoffe sowie sulfonamide als deren zwischenprodukte |
DE19626318A1 (de) * | 1996-07-01 | 1998-01-08 | Basf Ag | Farbstoffmischungen, enthaltend Polyazofarbstoffe |
KR100475413B1 (ko) * | 2001-11-22 | 2005-03-10 | 김진열 | 유기용제 가용형 폴리아닐린, 그 제조방법 및 그의 응용 |
KR101340101B1 (ko) * | 2006-05-16 | 2013-12-10 | 클라리언트 파이넌스 (비브이아이)리미티드 | 디스아조 산 염료 |
CN101177545B (zh) * | 2007-11-28 | 2011-02-23 | 上虞新晟化工工业有限公司 | 一种酸性红染料组合物 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1443541A (en) * | 1972-11-09 | 1976-07-21 | Basf Ag | Trisazo dyes |
DE2415690A1 (de) * | 1974-04-01 | 1975-10-23 | Basf Ag | Trisazofarbstoffe |
DE2416670A1 (de) * | 1974-04-05 | 1975-10-23 | Basf Ag | Trisazofarbstoffe |
DE3618265A1 (de) * | 1986-05-30 | 1987-12-03 | Basf Ag | Neue heterocyclenhaltige trisazofarbstoffe |
-
1995
- 1995-08-17 DE DE19530176A patent/DE19530176A1/de not_active Withdrawn
-
1996
- 1996-08-05 JP JP9508888A patent/JPH11511189A/ja active Pending
- 1996-08-05 CN CN96196331A patent/CN1193331A/zh active Pending
- 1996-08-05 EP EP96928410A patent/EP0850279A1/de not_active Withdrawn
- 1996-08-05 WO PCT/EP1996/003439 patent/WO1997007168A1/de not_active Application Discontinuation
- 1996-08-05 US US08/983,326 patent/US5834602A/en not_active Expired - Fee Related
- 1996-08-12 AR ARP960103965A patent/AR003252A1/es unknown
Also Published As
Publication number | Publication date |
---|---|
EP0850279A1 (de) | 1998-07-01 |
JPH11511189A (ja) | 1999-09-28 |
AR003252A1 (es) | 1998-07-08 |
WO1997007168A1 (de) | 1997-02-27 |
US5834602A (en) | 1998-11-10 |
DE19530176A1 (de) | 1997-02-20 |
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