CN1071717A - 纤维状材料的染色方法 - Google Patents
纤维状材料的染色方法 Download PDFInfo
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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
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- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/6426—Heterocyclic compounds
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- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
- D06P1/6495—Compounds containing carbonamide -RCON= (R=H or hydrocarbons)
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- 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
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/651—Compounds without nitrogen
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- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
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- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/242—Polyamides; Polyurethanes using basic dyes
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- D06P5/20—Physical treatments affecting dyeing, e.g. ultrasonic or electric
- D06P5/2044—Textile treatments at a pression higher than 1 atm
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- Y10S57/904—Flame retardant
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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
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- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract
本发明提供纤维状材料染色的方法。该方法包
括将纤维状材料与载体和可溶于或分散于载体的染
料的混合物相接触。其改进包括用N-环己基-2-吡
咯烷酮和苯甲酸烷基酯或芳基酯的混合物作为载
体。本发明的载体体系可有效地用于染色困难的纤
维状材料如包括Kevlar纤维和它们与其它纤维的
混纺纤维。
Description
本发明涉及纤维状材料的染色方法,特别是那些难于染色的纤维状材料,如芳族聚酰胺、聚苯并咪唑或芳族聚酰亚胺的染色。
进行染色和或将添加剂结合在纤维或其它纤维状材料上有许多熟悉的方法。这些方法主要包括利用如二甲亚砜(“DMSO”)、二甲基乙酰胺(“DMc”)、二甲基甲酰胺(“DMF”)。N-甲基吡咯烷酮(“NMP”)、苯乙酮、N-乙酰苯胺和苯甲酸甲酯之类的利用有机溶剂的方法。利用有机溶剂的方法的典型体系已在U.S.P.Nos.3,558,267(Langenfeld),3,741,719(Ramanathan等)和4,525,168(Kelly)以及U.K.P.Nos.1,275,459(Gruen)和1,282,113(Burtonshaw等)中提出。
已提出的一种特殊溶剂是N-环己基-2-吡咯烷酮(“CHP”),利用此特殊溶剂的方法是U.S.P.Nos.4,074,615(Lacroix等)提出的,是用乙二醇或乙二醇醚与N-环己基-2-吡咯烷酮结合去染聚酰胺纤维的;以及最近的U.S.P.Nos.4,898,596(Riggins等人),用以染色聚间苯二甲酰间苯二胺和聚苯并咪唑。
尽管包括N-环己基-2-吡咯烷酮在内的溶剂的染色方法的普遍有效,也继续希望有改进提高纤维可染性的方法,例如让染料基本上完全上染以及添加剂(如阻燃剂)的渗入纤维,对于难于染色的纤维这是特别重要的,例如芳族聚酰胺如聚间苯二甲酰间苯二胺(“Nomex
”)和聚对苯二甲酰对苯二胺(Kevlar
)、聚苯并咪唑(“PBI”)和芳族聚酰亚胺。
除了提高可染性的方法改进的愿望外,先有技术也认为对于任何体系的有效而均匀地染Kevlar
纤维和Kevlar
与其它纤维的混纺纱都是继续有必要的,此问题叙述于下列文章中,例如:“Evalution of the STX
System for Solvent Dyeing of Industrial Fabric,Part Ⅱ:Kevlar Aramid and PBI Fabrics”,Cook等,Journal of Industrial Fabrics,Vol.2,No.1,Summer 1983和U.S.P.4,898,596(Riggins等)。此问题对于最普遍供应的Nomex产品即Nomex
T-455是特别急需解决的。Nomex
T-455包括5%的Kevlar
,尽管对100%的Nomex
的染色方法是有效的,但没有对Nomex
T-455的Kevlar
组成部分均匀染色的有效方法。
因此,本发明的目的是提供纤维状材料染色的改进方法,特别是提供一种产生特别好的结果的染色方法,例如用于难于染色的诸如包括Kevlar
纤维、聚苯并咪唑纤维、芳族聚酰亚胺纤维以及它们的单体的共聚物和它们的混纺纱之类的纤维时,能够更均匀地染色。
本发明涉及纤维状材料的染色方法,该方法包括将纤维状材料与染料在一特别的由N-环己基-2-吡咯烷酮和-苯甲酸烷基酯或芳基酯的混合物组成的染料载体混合物(例如溶液或分散液)相接触。它的好处是,例如通过使用此混合物达到的更均匀的染色是特别惊奇的,因此苯甲酸烷基酯和芳基酯一类一般被认为在芳族聚酰胺、聚苯并咪唑和芳族聚酰亚胺的染色中用作载体是无效的。类似的,占优势的想法,如Riggins等的实施例中,是认为N-环己基-2-吡咯烷酮用于Kevlar
、Kevlar
与其它聚合物和纤维的共聚物或混纺纱的染色是无效的。
业已发现,N-环己基-2-吡咯烷酮和苯甲酸甲酯的混合物提供了一种特别有效的载体体系用于纤维状材料的均匀染色,特别是用于Nomex
、Kevlar
、聚苯并咪唑、聚酰亚胺、它们的单体的共聚物和它们的混纺纱。
如上所总结,本发明是提供一种改进的载体体系和染色的或以载体为基础的将添加剂结合到纤维状材料上的方法。此改进是用包括N-环己基-2-吡咯烷酮和苯甲酸烷基酯混合物的改进的染料载体,按照先有技术方法,染色是以形成染料和/或添加剂和本发明的载体的混合物(例如染浴溶液、分散液等)而进行的,本发明是将纤维织物材料例如纤维、纤维网、纱、线、纱条、机织织物、针织织物、非织造织物等进行浸渍、浸轧或者用常规设备(如喷射染色机)与染浴接触。
本发明的载体包括N-环己基-2-吡咯烷酮和苯甲酸烷基酯或芳基酯的混合物。适合的苯甲酸烷基酯包括苯甲酸乙酯、苯甲酸甲酯、苯甲酸丙酯、苯甲酸异丙酯、苯甲酸异丁酯等,适合的苯甲酸芳基酯包括苯甲酸苄基酯、苯甲酯苯基酯等,苯甲酸酯最好以乳化形式。特别优先选择的苯甲酸酯是苯甲酸甲酯,它是含约25-35%苯甲酸甲酯的乳液。本发明的载体体系中的N-环己基-2-吡咯烷酮与以乳液形式存在的苯甲酸烷基酯或芳基酯的比例为2∶3至8∶1左右,最优先选择的是4∶1左右。染浴中载体的总重为1-3%左右,基于染液重计算。重量百分数可用水或任何其它能与载体互相混溶的液体来调节。载体可包括其它添加剂,如阻燃剂、软化剂、UV吸收剂、IR吸收剂、抗静电剂、防泡剂或其它。
鉴于至今为止所取得的好结果,认为本发明的载体可适用于较广的纤维状材料并包括已经形成织物的纤维的染色,这些织物包括例如纺织品、非织造织物或针织品。典型的纤维最好包括如聚酯之类的合成纤维;聚烯烃,如聚乙烯、聚丙烯等;脂族聚酰胺,如尼龙-6、尼龙-66等;芳族聚酰胺;芳族聚亚胺;共聚物和它们的混纺纱。
如上已指出,载体特别适用于芳族聚酰胺,芳族聚酰胺纤维常总称为“aramid纤维”,叙述于例如Kirk-Othmer:The Encyclopedia of Chemical Technology,第3版,Vol.3,pp 213-242,现引用供参考。术语“芳族聚酰胺”或“aramid”包括(但不限于)聚间苯二甲酰间苯二胺(例如Nomex
)、聚对苯二甲酰对苯二胺(例如Nomex
)、聚对苯甲酰胺、它们的单体的共聚物和它们的混纺纱,Nomex
为杜邦产品(Wilmington,Delaware),有三种形式:Nomex
T-450为100%未染聚间苯二甲酰间苯二胺;Nomex
T-456,Nomex
T-456,为100%已染色的聚间苯二甲酰间苯二胺;Nomex
T-455为95% Nomex
和5%Kevlar
的混纺纱,Nomex
T-455与5%的Kevlar
是工业上最常用的Nomex
类型,鉴于本发明的载体对Nomex
T-455的Kevlar
组分在高于250°F左右的温度下有更均匀的染色能力,相信本发明的载体可在高于250°F左右的温度下能以更均匀的方式染其它纤维混纺纱。
另一组优先选择的纤维是聚苯并咪唑纤维,为Hoechst-Celanese of Charlotte,North Carolina产品,叙述于U.S.P.2,895,948(Brinker等人),现提出供参考。聚苯并咪唑使用特定的二羧酸和四胺化合物作为单体,并具有下式的重复单元:
另一组优先选择的纤维是芳族聚酰亚胺纤维,叙述于U.S.P.4,758,649(Asano等人),在此作为参考,芳族聚酰亚胺具有如下的重复单元:
此外,芳族聚酰胺单体的共聚物或芳族聚酰胺混合物、聚苯并咪唑和/或芳族聚酰亚胺可以用作纤维。例如,芳族聚酰胺纤维和聚苯并咪唑纤维可以60∶40-80∶20左右的重量比混纺。混纺纱可以是紧密混纺纱、拉伸混纺纱、包芯纺等。
用于本发明的适合的染料包括酸性染料(例如偶氮、三芳甲烷、蒽醌染料等);碱性染料(例如三苯甲烷、噻嗪染料等);直接染料(例如磺化偶氮染料等);媒染染料;还原染料;分散染料(例如硝基芳胺、有氨基的偶氮或蒽醌等染料)、直接染料、活性染料以及它们的混合物。对芳族聚酰胺纤维、聚苯并咪唑纤维和芳族聚酰亚胺纤维特别有效的染料是碱性染料(有时称为阳离子染料),这类染料的例子是Basacryl
染料,由BASF,Charlotte,North Carolina提供。
适于用作添加剂的阻燃剂可包括特别是那些基于环膦酸酯的化合物,例如Albright & Wilson of Richmond,Virginia提供的商标为Antiblaze 100
的产品,该产品叙述于U.S.P.3,789,091(Anderson等人)和U.S.P.4,397,759(Hancock),在此提出供参考。
在操作上,最好是将染料和/或添加剂用一步间歇型方法在100°F-300°F和1-3大气压下作用于织物的纤维,不需要对织物进行预处理。织物的染色可将织物通过喷射染色机经热水洗涤或其它加压洗涤设备洗涤,然后将喷嘴盛以本发明的载体和染料和/或添加剂,喷嘴工作时将温度升至250°F左右以上,最好是270°F,压力升至2.5大气压左右以上保护30分钟。将织物冷却,移出染浴,喷嘴盛湿润剂和苏打灰进行后洗涤,得到的织物,视上染在织物上的染料而定,一般有约70-98%染料,基于染浴中的染染料计算。
本发明的其它优点通过下述的解释性实例将变得比较明显。
实例
实例1
用含20g/l的含重量比为4∶1的N-环己基-2-吡咯烷酮/乳化苯甲酸甲酯的染浴进行染色。浴温设定在低于约120°F染色,10分钟,加入含3.75%Basaeryl 蓝 X-3GL、1.41%Basacryl 红GL和0.9%Basacryl 黄 X-GFL(纤维上重量)的海军蓝阳离子染料在喷嘴中喷射10分钟,加入20g/l硝酸钠(缓染剂),历时10分钟。接着加甲酸,将温度以3°F/分钟的增速增至270°F。然后在提高的温度约270°F和约2.85大气压下将织物延续染色60分钟。将已染的织物冷却至160°F并检查色泽。如果色泽合格,则滴干染液并将织物用冷水清洗干净。
在含0.125%润湿剂和0.5%苏打灰的浴中进行后洗涤,将温度升至180°F,在180°F下洗涤织物纤维20分钟。将织物冷却并进行清洗。直至清洗干净,然后将织物干燥。
织物的色泽是用视觉主观测定的并客观地分成L*、a*、b*级。后者是用Hunterlab of Fairfax,Virginia提供的设定在照度10°和有D65光源的比色计测定的。L*、a*、b*级是以色视觉的相对色理论为基础的,是假定的在人眼中的视网膜的光感器和光神经之间有一中间信号转换阶段将色信号传递至大脑,在此转换阶段,红色的响应与绿色比较,产生红至绿的色因次。绿色(或红和绿色一起,依赖于所用的理论)响应以类似的方法与蓝色比较,产生黄至蓝的色因次。两种因次常常(虽然不是经常)分别与“a*”和“b*”相关,必要的第三种因次“L*”(亮度)通常是非线性函数,如两种因次之一的平方根或立方根。另外还有△E值,可用下面的方程式测定以比较同类织物的色泽:
△E=[(△L)+(△a)+(△b)]
实例1的织物具有极好的海军蓝的色泽,其L*为18.54,a*为1.17,b*为-7.78,并且色泽是用来控制详述于下的实例中Nomex
T-455所得到的染料色泽的△E值的,换言之,用下面实例的色泽与实例1的色泽比较,测得的△E值愈低,织物的色泽愈相接近。
实例2
重复实例1的步骤,但使用的N-环己基-2-吡咯烷酮/乳化苯甲酸甲酯的重量比为3∶2,得到的织物色泽很好,其L*为19.02、a*为0.99、b*为-8.20,与用实例1的方法得到的色泽比较△E值为0.67。
实例3
重复实例1的步骤,但使用的N-环己基-2-吡咯烷酮/乳化苯甲酸甲酯的重量比为3∶2。所得到的织物色泽轻,其L*为19.93、a*为1.99、b*为-9.50,与用实例1的方法得到的色泽比较△E值为0.36。
实例4
重复实例1的步骤,但使用100%的乳化苯甲酸甲酯。所得到的织物基本上未染色,其L*为24.84,a*为5.69,b*为-23.73,此实例所得结果证实单独使用苯甲酸甲酯对芳族聚酰胺染色是无效的。
实例5
重复实例1的步骤,但使用100%的N-环己基-2-吡咯烷酮。
染得的织物有可见的不均匀性,特别是Kevlar
组分,与由实例1的方法得到的比较均匀的色泽相比,其L*为18.07,a*为1.35,b*为-6.69。此实例结果证实将苯甲酸甲酯包括在N-环己基-2-吡咯烷酮中的载体体系对于Kevlar
混合物能提供比较均匀的染色,如对Nomex
T-455纤维和其织物的染色。
实例6
为进一步证明本发明载体的有效性,本实例重复实例1的步骤,但使用100%的Kevlar
纤维和由4.875%Basacryl 蓝X-3GL、0.93%Basacryl 红 GL和1.00%Basacryl 黄X-GFL(织物上重量)组成的海军蓝阳离子染料。
实例7
所得到的染色织物具有均匀的蓝色色泽,其L*为19.82,a*为0.71,b*为-10.85。此实例证明在均匀染色PBI/Nomex
混纺纱时本发明载体的适合性。
实例8
本发明说明书及实例已经公开了本发明的最佳实施方案,虽然其中采用了特定的术语,但它们只是概括和描述性的,并非为了进行限制,本发明的范围是以下面的权利要求书所限定的。
Claims (14)
1、一种纤维状材料的染色方法。该方法包括将纤维状材料与载体和能溶于或分散于载体中的染料的混合物相接触。其特征在于该方法的改进包括使用N-环己基-2-吡咯烷酮和苯甲酸烷基酯或芳基酯的混合物作为载体。
2、权利要求1所述的方法,其中的纤维状材料是芳族聚酰胺、聚苯并咪唑、芳族聚酰亚胺、它们的单体共聚物或它们的混纺纱纤维。
3、权利要求2所述的方法,其中芳族聚酰胺是聚间苯二甲酰间苯二胺、聚对苯二甲酰对苯二胺、它们的单体共聚物或它们的混合物。
4、权利要求2所述的方法,其中的纤维包括芳族聚酰胺和聚苯并咪唑纤维的混纺纱纤维。
5、权利要求4所述的方法,其中混纺纱是芳族聚酰胺和聚苯并咪唑纤维,其重量比为约60∶40至约80∶20的混纺纱。
6、权利要求1所述的方法,其中N-环己基-2-吡咯烷酮/乳液状苯甲酸烷基酯或芳基酯的重量比为约2∶3至约8∶1。
7、权利要求6所述的方法,其中N-环己基-2-吡咯烷酮/乳液状苯甲酸烷基酯或芳基酯的重量比为约4∶1。
8、权利要求1所述的方法,其中溶于或分散于载体中的染料选自一组包括酸性染料。碱性染料、媒染染料、还原染料、分散染料、直接染料和活性染料的染料。
9、权利要求1所述的方法,其中载体和染料混合物包括阻燃添加剂。
10、权利要求1所述的方法,其中苯甲酸烷基酯或芳基酯是乳化的苯甲酸甲酯。
11、权利要求1所述的方法,其中上染在纤维状材料上的染料量为约70%至约98%,基于载体和染料混合物中染料的重量计算。
12、权利要求1所述的方法,其中纤维状材料在温度为约100°F至约300°F、压力为约1至3大气压下与载体和染料混合物接触。
13、权利要求12所述的方法,其中纤维状材料在温度为约250°F以上、压力为约2.5大气压以上与载体和染料混合物接触,并在此温度和压力下保持约30分钟至约1.5小时。
14、用权利要求2的方法染色纤维的织物。
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/525,776 US5092904A (en) | 1990-05-18 | 1990-05-18 | Method for dyeing fibrous materials |
CA002053074A CA2053074C (en) | 1990-05-18 | 1991-10-09 | Method for dyeing fibrous material |
AU85798/91A AU646095B2 (en) | 1990-05-18 | 1991-10-11 | Method for dyeing fibrous material |
DE69110677T DE69110677T2 (de) | 1990-05-18 | 1991-10-17 | Verfahren zum Färben von Fasermaterialien. |
AT91309603T ATE124100T1 (de) | 1990-05-18 | 1991-10-17 | Verfahren zum färben von fasermaterialien. |
JP3269346A JP2529789B2 (ja) | 1990-05-18 | 1991-10-17 | 繊維材料の染色方法 |
ES91309603T ES2073691T3 (es) | 1990-05-18 | 1991-10-17 | Metodo para teñir materiales fibrosos. |
EP91309603A EP0537396B1 (en) | 1990-05-18 | 1991-10-17 | Method of dyeing fibrous materials |
DK91309603.8T DK0537396T3 (da) | 1990-05-18 | 1991-10-17 | Fremgangsmåde til forarbejdning af fibrøse materialer |
CN91109829A CN1071717A (zh) | 1990-05-18 | 1991-10-23 | 纤维状材料的染色方法 |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/525,776 US5092904A (en) | 1990-05-18 | 1990-05-18 | Method for dyeing fibrous materials |
CA002053074A CA2053074C (en) | 1990-05-18 | 1991-10-09 | Method for dyeing fibrous material |
AU85798/91A AU646095B2 (en) | 1990-05-18 | 1991-10-11 | Method for dyeing fibrous material |
JP3269346A JP2529789B2 (ja) | 1990-05-18 | 1991-10-17 | 繊維材料の染色方法 |
CN91109829A CN1071717A (zh) | 1990-05-18 | 1991-10-23 | 纤维状材料的染色方法 |
Publications (1)
Publication Number | Publication Date |
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CN1071717A true CN1071717A (zh) | 1993-05-05 |
Family
ID=27507278
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN91109829A Pending CN1071717A (zh) | 1990-05-18 | 1991-10-23 | 纤维状材料的染色方法 |
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Country | Link |
---|---|
US (1) | US5092904A (zh) |
EP (1) | EP0537396B1 (zh) |
JP (1) | JP2529789B2 (zh) |
CN (1) | CN1071717A (zh) |
AT (1) | ATE124100T1 (zh) |
AU (1) | AU646095B2 (zh) |
CA (1) | CA2053074C (zh) |
DE (1) | DE69110677T2 (zh) |
DK (1) | DK0537396T3 (zh) |
ES (1) | ES2073691T3 (zh) |
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US5824614A (en) * | 1997-04-24 | 1998-10-20 | Basf Corporation | Articles having a chambray appearance and process for making them |
US6265082B1 (en) | 1998-04-09 | 2001-07-24 | Kevin L. Dunham | Fire retardant compositions and methods for their preparation and use |
US20050204487A1 (en) * | 2004-03-18 | 2005-09-22 | Reiyao Zhu | Dyeing of modacrylic/aramid fiber blends |
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-
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-
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- 1991-10-09 CA CA002053074A patent/CA2053074C/en not_active Expired - Fee Related
- 1991-10-11 AU AU85798/91A patent/AU646095B2/en not_active Ceased
- 1991-10-17 DK DK91309603.8T patent/DK0537396T3/da active
- 1991-10-17 AT AT91309603T patent/ATE124100T1/de not_active IP Right Cessation
- 1991-10-17 EP EP91309603A patent/EP0537396B1/en not_active Expired - Lifetime
- 1991-10-17 ES ES91309603T patent/ES2073691T3/es not_active Expired - Lifetime
- 1991-10-17 JP JP3269346A patent/JP2529789B2/ja not_active Expired - Lifetime
- 1991-10-17 DE DE69110677T patent/DE69110677T2/de not_active Expired - Fee Related
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Also Published As
Publication number | Publication date |
---|---|
DE69110677T2 (de) | 1996-01-25 |
EP0537396B1 (en) | 1995-06-21 |
CA2053074A1 (en) | 1993-04-10 |
ES2073691T3 (es) | 1995-08-16 |
US5092904A (en) | 1992-03-03 |
EP0537396A1 (en) | 1993-04-21 |
CA2053074C (en) | 1998-09-15 |
ATE124100T1 (de) | 1995-07-15 |
JPH073662A (ja) | 1995-01-06 |
DK0537396T3 (da) | 1995-11-27 |
JP2529789B2 (ja) | 1996-09-04 |
AU646095B2 (en) | 1994-02-10 |
AU8579891A (en) | 1993-06-17 |
DE69110677D1 (de) | 1995-07-27 |
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