CN1209151A - 含有氟磺酰基的单偶氮类染料及其应用 - Google Patents
含有氟磺酰基的单偶氮类染料及其应用 Download PDFInfo
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- 239000000975 dye Substances 0.000 title claims abstract description 29
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title abstract description 4
- 239000000463 material Substances 0.000 claims abstract description 25
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- 239000004758 synthetic textile Substances 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims description 19
- 239000000835 fiber Substances 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- DXBICNXFLXEILE-UHFFFAOYSA-N ClNC1=CC=C(C=C1)S(=O)(=O)F Chemical compound ClNC1=CC=C(C=C1)S(=O)(=O)F DXBICNXFLXEILE-UHFFFAOYSA-N 0.000 claims description 5
- 150000004982 aromatic amines Chemical class 0.000 claims description 5
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 238000006193 diazotization reaction Methods 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 2
- 150000001989 diazonium salts Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 229910006095 SO2F Inorganic materials 0.000 abstract 1
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 1
- 238000004040 coloring Methods 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 description 10
- -1 fluorosulfonyl Chemical group 0.000 description 9
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
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- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- 125000003118 aryl group Chemical group 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
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- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- 229920002239 polyacrylonitrile Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
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- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical group OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- UGHWQYDRRDQBGY-UHFFFAOYSA-N 2-acetyloxyethyl 3-(n-ethyl-3-methylanilino)propanoate Chemical compound CC(=O)OCCOC(=O)CCN(CC)C1=CC=CC(C)=C1 UGHWQYDRRDQBGY-UHFFFAOYSA-N 0.000 description 1
- VVHJNAXAJRNVBG-UHFFFAOYSA-N 2-chloroethyl 3-(n-ethyl-3-methylanilino)propanoate Chemical compound ClCCOC(=O)CCN(CC)C1=CC=CC(C)=C1 VVHJNAXAJRNVBG-UHFFFAOYSA-N 0.000 description 1
- 229940061334 2-phenylphenol Drugs 0.000 description 1
- OUERGFXVDNRRDO-UHFFFAOYSA-N 3-chloropropyl 3-(n-ethyl-3-methylanilino)propanoate Chemical compound ClCCCOC(=O)CCN(CC)C1=CC=CC(C)=C1 OUERGFXVDNRRDO-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 229920002284 Cellulose triacetate Chemical group 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical group O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000000498 ball milling Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000010296 bead milling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000010014 continuous dyeing Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical class [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 238000010017 direct printing Methods 0.000 description 1
- 238000010018 discharge printing Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- BLLFVUPNHCTMSV-UHFFFAOYSA-N methyl nitrite Chemical compound CON=O BLLFVUPNHCTMSV-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229950000244 sulfanilic acid Drugs 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0815—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)-
- C09B29/0816—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)- substituted by -COOR
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
-
- 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
- Y10S8/922—Polyester fiber
-
- 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)
Abstract
式(1)所示的单偶氮染料,其中R1表示－C3H6CN、－C2H4Cl、－C3H6Cl、－C2H4OCOCH3或－C2H4OCOCH2Cl;R2和R3各自表示C1－6烷基;R4、R5和R6各自表示H、F、Cl、Br、I、－SO2F,或选自C1－6烷基、C1－6烷氧基、C1－4烷酰氨基、－NHSO2烷基、－NHCOC1－4烷基和－O－苯基的有机基团,其中的每个有机基团是非取代的或被一个或多个非离子取代基取代。该染料可用于合成纤维纺织品材料的染色。
Description
本发明涉及含有氟磺酰基的偶氮类染料、特别是水不溶性单偶氮类染料，其制备方法及其用于染色合成纤维纺织品和其它材料的应用。
公开于WO 95/20014的国际专利申请描述了含有至少一个氟磺酰基且不含水溶性基团的偶氮类化合物。其中还描述了这些化合物用于合成纤维纺织品材料的染色和用于塑料的本体染色的应用。
当作为合成纤维纺织品材料的分散染料时，我们发现某些染料显示优越性质，这些染料属于WO 95/20014中概述的化合物，但没有在其中具体公开。
因此，本发明提供分子式如下的单偶氮染料：其中：
R1表示-C3H6CN,-C2H4Cl,-C3H6Cl,-C2H4OCOCH3或-C2H4OCOCH2Cl；
R2和R3各自表示C1-6烷基；和
R4,R5和R6各自表示H、F、Cl、Br、I、-SO2F，或选自C1-6烷基、C1-6烷氧基、C1-4烷酰氨基、-NHSO2烷基、-NHCOC1-4烷基和-O-苯基的有机基团，每个有机基团是非取代的或被一个或多个非离子取代基取代。
在分子式1中由R2和R3表示的含有3-6个碳原子的烷基基团可以是直链或支链烷基基团，但R2优选为乙基和R3优选为甲基。
优选R4和R5中的至少一个为H，特别优选R4和R5都为H，特别优选R4、R5和R6均为H。
由R4-R6表示的基团上可有可无的非离子取代基特别包括-CN、-OH、-OC1-6-烷基、-OCOC1-6-烷基、-COOC1-6-烷基、苯基、苯氧基、-OCO苯基、-OCO苯基SO2F、苯基SO2F、苯基SO2F、-CO2苯基SO2F。
式1的染料可以通过重氮化2,5-二氯-4-氟磺酰基苯胺、并且将得到的重氮化合物与芳香胺偶联制备，该芳香胺的结构式为：
其中R1-R6如上文定义。
重氮化和偶联反应可以使用所用反应类型的常用反应条件进行。典型地是，在-10℃-10℃的温度下在酸性介质(如乙酸、丙酸或盐酸)中，使用亚硝基化剂(如亚硝基硫酸、亚硝酸钠或亚硝酸甲酯)将2,5-二氯-4-氟磺酰基苯胺重氮化。可以在0℃-10℃的温度下在链烷醇中通过往式2的胺中加入重氮化的2,5-二氯-4-氟磺酰基苯胺实现与式2的芳香胺的偶联，链烷醇优选为C1-4链烷醇，如甲醇。偶联后，式1的化合物可以从反应混合物中用任何简便方法(如过滤)回收。
式1的偶氮化合物可用作分散染料，并且对合成纤维纺织品材料的染色和含有此类材料的混合纤维很重要。
合成纤维纺织品材料可以选自二级乙酸纤维素、三乙酸纤维素、聚酰胺、聚丙烯腈和芳族聚酯。合成纤维纺织品材料优选为聚酰胺如聚亚己基己二酰胺，或芳族聚酯、特别是聚对苯二甲酸乙二醇酯。混合纤维可以包括不同合成纤维纺织品材料的混合物或合成和天然纤维纺织品材料的混合物。优选的混合纤维包括那些聚酯-纤维素如聚酯-棉。纺织品材料或其混合可以呈长丝、散纤维、纱或织物或针织物的形式。
通过使用常规的方法，可以将式1的偶氮化合物或其混合物以及可有可无的其它分散染料施用于合成纤维纺织品材料或其混合纤维上。
适宜的工艺条件如下：1)在压力为1-2巴，温度为125℃-140℃,pH为4-6.5的条件下浸染10-120分钟，可非强制性地加入多价螯合剂；2)在温度为190℃-225℃,pH为4-6.5的条件下连续染色15秒-5分钟，可非强制性地加入迁移抑制剂；3)在pH为4-6.5，温度为160℃-185℃的高温汽蒸的条件下直接印花4-15分钟，或在190℃-200℃，用干热烘干固色15秒-5分钟或在120℃-140℃和1-2巴压力下汽蒸10-45分钟，可非强制性地加入染料重量的5-100％的润湿剂和增稠剂(如藻酸盐类)；4)在pH为4-6.5的条件下拔染印花(在纺织品材料上浸轧染料，干燥并套印)，可非强制性地加入迁移抑制剂和增稠剂；5)在pH为4-6.5，温度为95℃-100℃的条件下，使用如甲基萘、二苯胺或2-苯基苯酚为染色载体进行载体染色，可非强制性地加入多价螯合剂；和6)在pH为4-6.5、醋酯纤维为85℃或三醋酸酯纤维和尼龙为90℃条件下常压染色醋酯纤维、三醋酸酯纤维和尼龙15-90分钟，可非强制性地加入多价螯合剂。
在所有的上述工艺中，式1的化合物或其混合物可以在含水介质中包括0.001％-4％重量的偶氮化合物或其混合物的分散体系使用。
染料分散体系可进一步包括通常用于染色应用中的成分，例如，分散剂如木素磺酸盐、萘磺酸/甲醛缩合物或苯酚/甲酚/对氨基苯磺酸/甲醛缩合物，表面活性剂，润湿剂如可被磺化或磷酸化的烷芳基乙氧基化物，无机盐类，消泡剂如矿物油或壬醇，有机液体和缓冲剂。分散剂可以为式1的偶氮化合物重量的10％-200％。使用的润湿剂可为式1的偶氮化合物重量的0％-20％。
适宜的分散体系可在含水介质中通过用玻璃小珠或砂子球磨(beadmilling)式1的化合物而制备。
式1的化合物能为合成纤维纺织品材料提供呈现出耐洗、耐光和热的红色。
式1的偶氮化合物也可用于塑料材料的本体染色。偶氮化合物通常与粒状或粉状塑料材料掺和混用，例如使用干法滚抛(dry tumbling)或高速混合，随后在螺杆机上注塑或用常规混合/母炼胶的技术成型。通常，本发明染料溶解和快速分散在热的塑料熔融物中，并提供具有良好透明度和良好耐光性的明亮颜色。可用这种方法染色的塑料包括聚苯乙烯，聚丙烯酸类，聚苯乙烯/丙烯腈混合物，聚丙烯腈/丁二烯/苯乙烯混合物，聚碳酸酯，聚醚砜，尼龙，硬质PVC(uPVC)和聚丙烯。
式1的偶氮化合物也可作为油墨色料用于基于溶剂的喷墨印花工艺中。一般情况下，这些基于酮类和/或醇类的油墨用于在疏水基质(如塑料和金属)上印花。
本发明用下列实施例说明，但不限于此，除非另外指出，实施例中所有份数以重量计。所有λmax值是在CH2Cl2中测定的。
实施例1
在0-5℃搅拌2,5-二氯-4-氟磺酰基苯胺(2份)和乙酸/丙酸混合物(15份，86/14体积/体积)的混合物，在该混合物中滴加亚硝基硫酸溶液(5份)。在此温度下进一步搅拌该混合物15分钟。在0-5℃搅拌下，将该重氮溶液缓慢加入到N-乙基-N-(2-(3-氰基丙氧基羰基)乙基)-3-甲苯胺(2.6份)、甲醇(50份)、水(20份)和氨基磺酸(0.5份)的混合物中。在此温度搅拌3小时后，过滤分离产物，用水洗涤并在50℃干燥，得到3-甲基-4-(2,5-二氯-4-氟磺酰基苯偶氮基)-N-乙基-N-(2-(3-氰基丙氧基羰基)乙基)苯胺(2.6份)。当从水分散体中施用于聚酯材料上时，染料(λmax=515nm)呈现出具有极好的耐光性和极好的耐湿加工性的蓝红色色调。
该种染料(其中分子式1中R1为-C3H6CN)的染色与WO95/20014的实施例63获得的染料(其中R1为-C2H4CN)的染色相比表现出优良的接触坚牢度。
实施例2
重复实施例1中描述的制备过程，用2.4份N-乙基-N-(2-(2-氯乙氧基羰基)乙基)-3-甲苯胺代替2.6份N-乙基-N-(2-(3-氰基丙氧基羰基)乙基)-3-甲苯胺。得到相似的红色染料(λmax=517nm)，当从水分散体中施用于聚酯材料上时，染料呈现出具有极好的耐光性和耐湿加工性的蓝红色色调。
实施例3
重复实施例1中描述的制备过程，用2.7份N-乙基-N-(2-(2-乙酸基乙氧基羰基)乙基)-3-甲苯胺代替2.6份N-乙基-N-(2-(3-氰基丙氧基羰基)乙基)-3-甲苯胺。得到相似的红色染料(λmax=515nm)，当从水分散体中施用于聚酯材料上时，染料呈现出具有极好的耐光性和耐湿加工性的蓝红色色调。
实施例4
重复实施例1中描述的制备过程，用2.9份N-乙基-N-(2-(2-(氯代乙酸基)乙氧基羰基)乙基)-3-甲苯胺代替2.6份N-乙基-N-(2-(3-氰基丙氧基羰基)乙基)-3-甲苯胺。得到相似的红色染料(λmax=515nm)，当从水分散体中施用于聚酯材料上时，染料呈现出具有极好的耐光性和耐湿加工性的蓝红色色调。
实施例5
重复实施例1中描述的制备过程，用2.7份N-乙基-N-(2-(3-氯代丙氧基羰基)乙基)-3-甲苯胺代替2.6份N-乙基-N-(2-(3-氰基丙氧基羰基)乙基)-3-甲苯胺。得到相似的红色染料(λmax=516nm)，当从水分散体中施用于聚酯材料上时，染料呈现出具有极好的耐光性和耐湿加工性的蓝红色色调。
Claims (6)
1．一种单偶氮染料，其结构式为：
其中：
R1表示-C3H6CN、-C2H4Cl、-C3H6Cl、-C2H4OCOCH3或-C2H4OCOCH2Cl；
R2和R3各自表示C1-6烷基；和
R4、R5和R6各自表示H、F、Cl、Br、I、-SO2F，或选自C1-6烷基、C1-6烷氧基、C1-4烷酰氨基、-NHSO2烷基、-NHCOC1-4烷基和-O苯基的有机基团，每个有机基团是非取代的或被一个或多个非离子取代基取代。
2．按照权利要求1的单偶氮染料，其中R2为乙基和R3为甲基。
3．按照权利要求1或2的单偶氮染料，其中R4和R5中的至少一个为H，并且优选R4和R5都为H。
4．按照权利要求3的单偶氮染料，其中R4、R5和R6均为H。
5．制备权利要求1的单偶氮染料的方法，它包括，重氮化2,5-二氯-4-氟磺酰基苯胺，并将得到的重氮化合物产物与芳香胺偶联，该芳香胺的分子式为：
其中R1和R6如权利要求1中所定义。
6．一种将合成纤维纺织品材料或其混合纤维染色的方法，它包括将权利要求1-4中任何一项的单偶氮染料施用于合成纤维纺织品材料或其混合纤维上。
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9601644.9A GB9601644D0 (en) | 1996-01-26 | 1996-01-26 | Azo gloves |
| GB9601644.9 | 1996-01-26 | ||
| GB9607599.9 | 1996-04-12 | ||
| GBGB9607599.9A GB9607599D0 (en) | 1996-04-12 | 1996-04-12 | Azo dyes |
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| Publication Number | Publication Date |
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| CN1209151A true CN1209151A (zh) | 1999-02-24 |
| CN1084768C CN1084768C (zh) | 2002-05-15 |
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| CN96180121A Expired - Lifetime CN1084768C (zh) | 1996-01-26 | 1996-12-16 | 含有氟磺酰基的单偶氮类染料及其应用 |
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| US (1) | US5998592A (zh) |
| EP (1) | EP0876429B1 (zh) |
| JP (1) | JP3989547B2 (zh) |
| KR (1) | KR100415949B1 (zh) |
| CN (1) | CN1084768C (zh) |
| AU (1) | AU1182297A (zh) |
| BR (1) | BR9612760A (zh) |
| DE (1) | DE69608133T2 (zh) |
| PT (1) | PT876429E (zh) |
| WO (1) | WO1997027247A1 (zh) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107227480A (zh) * | 2017-05-27 | 2017-10-03 | 北京石油化工学院 | 一种利用弱酸性染料为镁材微弧氧化膜层着色的方法 |
| CN107227479A (zh) * | 2017-05-27 | 2017-10-03 | 北京石油化工学院 | 一种利用分散性染料为镁材微弧氧化膜层着色的方法 |
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| KR20030097245A (ko) * | 2002-06-20 | 2003-12-31 | 대한민국(서울대학교 총장) | 플루오로술폰기를 가지는 아조계 알칼리 세정성 분산염료,그 제조방법 및 그를 이용한 염색방법 |
| GB0625624D0 (en) * | 2006-12-21 | 2007-01-31 | Dystar Textilfarben Gmbh & Co | Disperse dye mixtures |
| JP2013515811A (ja) * | 2009-12-23 | 2013-05-09 | カラーテックス・インダストリーズ・リミテッド | 分散染料 |
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| GB9400972D0 (en) * | 1994-01-19 | 1994-03-16 | Zeneca Ltd | Process |
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1996
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- 1996-12-16 WO PCT/GB1996/003093 patent/WO1997027247A1/en active IP Right Grant
- 1996-12-16 JP JP52662497A patent/JP3989547B2/ja not_active Expired - Fee Related
- 1996-12-16 EP EP96942453A patent/EP0876429B1/en not_active Expired - Lifetime
- 1996-12-16 AU AU11822/97A patent/AU1182297A/en not_active Abandoned
- 1996-12-16 BR BR9612760-0A patent/BR9612760A/pt not_active IP Right Cessation
- 1996-12-16 CN CN96180121A patent/CN1084768C/zh not_active Expired - Lifetime
- 1996-12-16 PT PT96942453T patent/PT876429E/pt unknown
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107227480A (zh) * | 2017-05-27 | 2017-10-03 | 北京石油化工学院 | 一种利用弱酸性染料为镁材微弧氧化膜层着色的方法 |
| CN107227479A (zh) * | 2017-05-27 | 2017-10-03 | 北京石油化工学院 | 一种利用分散性染料为镁材微弧氧化膜层着色的方法 |
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| Publication number | Publication date |
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| JP3989547B2 (ja) | 2007-10-10 |
| DE69608133D1 (de) | 2000-06-08 |
| JP2000504046A (ja) | 2000-04-04 |
| EP0876429A1 (en) | 1998-11-11 |
| AU1182297A (en) | 1997-08-20 |
| BR9612760A (pt) | 2001-01-09 |
| DE69608133T2 (de) | 2000-09-28 |
| CN1084768C (zh) | 2002-05-15 |
| WO1997027247A1 (en) | 1997-07-31 |
| PT876429E (pt) | 2000-08-31 |
| KR100415949B1 (ko) | 2005-09-14 |
| US5998592A (en) | 1999-12-07 |
| KR19990081984A (ko) | 1999-11-15 |
| EP0876429B1 (en) | 2000-05-03 |
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