CN1124306A - 用聚合胺化合物改性的人造纤维 - Google Patents
用聚合胺化合物改性的人造纤维 Download PDFInfo
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- CN1124306A CN1124306A CN95108112A CN95108112A CN1124306A CN 1124306 A CN1124306 A CN 1124306A CN 95108112 A CN95108112 A CN 95108112A CN 95108112 A CN95108112 A CN 95108112A CN 1124306 A CN1124306 A CN 1124306A
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Classifications
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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
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/22—Effecting variation of dye affinity on textile material by chemical means that react with the fibre
- D06P5/225—Aminalization of cellulose; introducing aminogroups into cellulose
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
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- D—TEXTILES; PAPER
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- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/10—Other agents for modifying properties
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- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
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- D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
- D01F2/02—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from solutions of cellulose in acids, bases or salts
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- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
- D01F2/02—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from solutions of cellulose in acids, bases or salts
- D01F2/04—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from solutions of cellulose in acids, bases or salts from cuprammonium solutions
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- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
- D01F2/06—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from viscose
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- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
- D01F2/06—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from viscose
- D01F2/08—Composition of the spinning solution or the bath
- D01F2/10—Addition to the spinning solution or spinning bath of substances which exert their effect equally well in either
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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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- 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
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- D06P3/6008—Natural or regenerated cellulose using acid dyes
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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
- D06P3/66—Natural or regenerated cellulose using reactive dyes
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- D—TEXTILES; PAPER
- D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
- D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
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- D10B2201/20—Cellulose-derived artificial fibres
- D10B2201/22—Cellulose-derived artificial fibres made from cellulose solutions
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- D—TEXTILES; PAPER
- D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
- D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
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- D10B2201/20—Cellulose-derived artificial fibres
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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
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- Y10S8/92—Synthetic fiber dyeing
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- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
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- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
本发明公开了向纤维素溶液中加入改性剂并从该溶液中纺丝、或者向粘胶溶液中加入改性剂并用粘胶纺丝法纺丝得到的改性纤维素纤维，所述改性剂是具有伯、仲或叔胺侧基且分子量大于1000的聚合胺化合物。
Description
本发明涉及用聚合胺化合物改性的纤维素纤维，所述改性纤维素纤维改进了染色性能，并且提高了干态和湿态纤维强度。
溶液纺丝得到的纤维素纤维与棉纤维具有基本相同的染色性能。目前，为了用活性染料得到满意的固定效果，天然或再生纤维素纤维的染色需要给出碱的试剂以及电解质盐。但是，这些添加用料对生态环境有害。未来需要不用盐和碱就能染色的再生纤维素纤维。一种解决方法是改性这些粘胶纤维，使它们的化学性质类似于动物纤维如羊毛或丝，不需再添加盐或碱、用阴离子染料在中性条件下就可染色。
粘胶纤维的改性已经公开于文献中，例如：
US—A—3,793,419公开了改进染色性能的粘胶纤维的制备方法。但是，该方法非常复杂，并且不经济。此外，该方法使用了主要为亲脂结构的多胺酰胺，这严重影响了纤维的固有性能。这一点从染色时使用的分散染料可明显看出。
同样地，已知加入胺化合物可改进粘胶纤维的物理性能。除公开了多种单体或低聚胺以外，还公开了如聚乙氧化的胺或多亚烷基多胺的聚合物。这方面的论述可参见K.Gtze，Chemiefasern nach demViskoseverfahren，Springer Verlag 1967，635ff。
同样地，US—A—3,305,377公开了胺基化的纤维。添料是高浓度的氨乙基—和二乙氨基乙基—纤维素，并且无一例外地用酸性染料染色。
US—A—4,806,126、US—A—4,988,365和CA—A—2084585公开了各种含氨基化合物，它用于在染色前预处理纤维素纤维织物的表面。这些方法的缺点是在改性过程中需要另外的处理步骤，并且使粘胶纤维泛黄。
本发明的目的是提供新颖的改性粘胶纤维，由其组成的织物可以无需添加盐和碱用活性染料染色，并克服了先有技术的上述缺点。
令人惊奇地发现，向粘胶纺丝溶液或纤维素溶液中混入下述改性剂，可以达到上述目的。
本发明纤维用活性染料染色时可以无需添加碱和盐。也可以用酸性染料染色。
此外，这些纤维如果用粘胶工艺纺丝，与传统粘胶纤维相比，在干态和湿态都具有较高的断裂强度和断裂伸长。
因此，本发明提供由下述方法制得的改性纤维素纤维：向纤维素溶液中加入改性剂、并用该溶液纺丝，或者向粘胶溶液中加入改性剂，并用粘胶纺丝工艺纺丝，其中，所述改性剂是分子量大于1000、优选大于20000，具有伯、仲和叔胺侧基的聚合胺化合物。
优选的改性剂是分子量大于20000、特别是大于50000，具有式(1)、(2)和/或(3)所示结构单元的聚合胺化合物；
(1)
(2)
(3)
其中，
R1和R2可相同或不同，每个表示氢原子，C1—C4烷基，未取代的苯基或被选自C1—C4烷基、C1—C4烷氧基或卤原子的至多3个基团取代的苯基，所述卤原子优选氟、氯和溴原子；
R3是氢原子，甲基或乙基；
R4是氢原子，甲基或乙基；
m为1—4；以及
O为0—4。
特别优选的是其中的R1和R2相互独立地表示氢原子、甲基或乙基，m为1—2，并且O为0—2的改性剂，尤其是聚乙烯基胺。同样的，本发明也可以使用不同聚合胺化合物的混合物作为改性剂。
本发明使用的聚合胺化合物可用本领域熟练技术人员熟知的方法制备，如用类似于美国专利No3,544,363中公开的聚亚胺的制备方法。
为了使改性剂能吸留在纤维中，并且在随后的凝结、拉伸和洗涤过程中不被洗掉，改性剂需有较高的分子量、即较长的分子链。改性剂吸留在纤维中不会改进纤维的物理性能，但为了改进纤维的染色性能，必须使改性剂吸留在纤维中。
使本发明的改性剂有有效量的吸留在纤维中的最小分子量为1000，优选大于20,000；分子量大于50,000时达到极好的效果。
在凝聚和成型前，吸留在本发明纤维素纤维中的改性剂量应为0.1％—10％重量、优选0.3％—3％重量(基于纺丝溶液中的纤维素含量)。改性剂的用量决定于侧氨基的数量。
如果用粘胶纺丝工艺制备本发明纤维，首先将纤维素碱煮解(碱纤维素)，然后与二硫化碳反应，并溶于水或碱金属氢氧化钠的稀溶液中，然后向该粘胶溶液中加入改性剂。在另一实施方案中，直接向用碱金属氢氧化物煮解的溶液中加入改性剂，然后使改性的碱纤维素与二硫化碳反应，形成黄原酸盐。在碱煮解时加入改性剂提高了纤维素黄原酸化的活性。这样得到的纺丝溶液的可滤过性较好，并且可减少CS2或碱金属氢氧化物溶液的用量。与二硫化碳的反应优选在15℃—30℃进行。溶解后，随后在酸性纺丝浴中纺丝得到本发明改性纤维素纤维。
如果用其它从溶液制备纤维素纤维的常规方法制备本发明纤维，例如用库普罗(cupro)方法、利阿塞尔(lyocell)方法和通过低取代纤维素醚的方法，那么，将纤维素溶于适宜有机溶剂中，与改性剂混合，并直接从溶液中纺丝。最好是在纺丝前加入改性剂，在这种情况下，可用已知搅拌系统(静态或动态混合系统)将它们混合均匀。但也可以在制备纺丝原液的任何希望的步骤中加入改性剂。
本发明改性剂的优点是使用简便，因为它可以无需溶剂、直接掺入纺丝原液或碱化的碱金属氢氧化物溶液中，或者以浓度大于50％的含水配方(如需要，借助于乳化剂)掺入。
这样，一方面可以达到高的吸留率，另一方面又可避免由于稀释作用对纤维物理性能的不利影响。
本发明改性剂特别适用于粘胶纤维，这是因为它既可以改进纤维的染色性能，又可以改进纤维的物理性能。
加入改性剂后，可用已知的纤维制备方法进一步处理纺丝溶液。不需要对这些方法作大的改动。使用粘胶纺丝工艺时，根据使用的改性剂可改变操作指数，如采用较大的拉伸率。
与没有加改性剂的样品相比，粘胶液的可滤过性没有受到影响，因此在纺丝过程中不会堵塞纺丝头。如果在碱化过程中加入改性剂，可改进可滤过性。用已知的常规方法形成粘胶纤维，例如借助于喷丝头及随后的凝固和(如需要)后处理浴。
例如与聚亚烷基聚胺的主链中的氨基相比，在相同的氨官能基数目下，本发明的侧氨基可以使上染率高、染料分子固定得好，并且有更好的坚牢度。
用本发明改性纤维素纤维加工成的纺织物和针织物可用各种方法用活性染料染色，如尽染法、轧染法和现代印花法(包括喷墨法)，染色时无需添加电解质盐或碱。
与传统粘胶纤维相比，本发明纤维与活性染料具有更强的亲合力，而在其它希望的性能上(如手感)与传统粘胶纤维几乎没有差别。
用粘胶纺丝法或从溶液中纺丝得到的本发明纤维可以不用添加碱和盐用活性染料染色，还可以用酸性染料染色。此外，用粘胶纺丝法得到的本发明纤维素纤维还显著提高了干态和湿态强度。
用于随后染色的改性纤维材料织物可呈各种形态，如纺纱、短纤、针织物、头道粗纱和匹布(纺织物)。
用上述方法得到的纤维可以短纤形式、或者加工成片状(如纺织物、针织物或无纺物)后，用各种方法如尽染法、轧染法或印花法直接染色，此间无需添加盐和碱。除了直接和活性染料外，还可以使用酸性染料。
根据本发明，用类似的染色和印花纤维材料的已知方法，采用水溶性织物染料在常规染色温度范围和染料量下将改性的织物纤维材料染色，但与传统纤维活性染料不同，不再需要为固定纤维活性染料而向染浴、轧染浴、印花色浆和喷墨染浴配方中加入碱化合物，也不需加入电解质盐。
适宜染色方法例如包括各种尽染法，如在卷染机上染色、在绞盘式绳状染色机上染色、或者用大或小浴比染浴染色、在喷染机上染色、用短时浸轧卷堆方法染色或用轧染过热汽蒸固定法染色。适宜印花方法包括传统印花方法，如喷染印花和转移印花。
用于染色该改性纤维素的染料通常为阴离子型的，特别适宜的是纤维活性织物染料，它们可以与如纤维素的羟基，或者与羊毛和丝、或如聚酰胺的合成聚合物、或者本发明胺化的纤维素的氨基和巯基反应，形成共价键。在织物染料上的适宜纤维活性基团特别包括硫酸根合乙基磺酰基、乙烯基磺酰基、氯代三嗪基、氟代三嗪基以及它们的组合。
适于染色或印花根据本发明改性的纤维素纤维的活性染料包括所有水溶性、优选阴离子型染料，它们优选具有1个或多个磺酸基和/或羟基，并且含有纤维活性基团。它们可以是偶氮染料、直接染料、还原染料、酸性染料，铜配位、钴配位和铬配位染料，铜和镍酞菁染料，蒽醌，甲铜，甲亚胺，硝基芳基，二恶嗪，三吩二恶嗪(triphendioxazine)，吩嗪和芪染料。这些染料已公开于许多文献中，如公开于US—A—5 403 361中，是本领域技术人员熟知的。
除非另外说明，下列实施例中的份数为重量份。
实施例1
将2800份纤维素含量为9％、碱含量为5.5％以及在30℃的粘度为40秒(落球试验)的常规纺丝粘胶与15.1g聚乙烯基胺水性制剂混合，该制剂含有约12％重量Fikentsher K值为120的聚乙烯基胺。
基于纤维素的量，其用量为0.7％。脱挥发分后，用常规粘胶纺丝方法将纺丝原液纺到含有硫酸、硫酸钠和硫酸锌的水浴中。将得到的丝束在酸性浴中拉伸，切丝，洗涤，纺丝整理并干燥。
实施例2
重复实施例1，只是将酸性浴中的拉伸提高10％。
对比例
对了对比，在实施例1的条件下，不加入改性剂，将纺丝原液纺成纤维。
纤维性能：性能 单位 实施例1 实施例2 对比例线密度 dtex 1.44 1.33 1.45强度 cN/tex 27.3 30.1 24.5伸长率 ％ 19.5 19.0 19.2湿强度 cN/tex 14.1 15.2 12.1
染色性能：
在下述条件下将纤维染色：
染色方法1(活性染料)：
在浴比为25∶1下，在1g/升浓度为40％的氢氧化钠溶液、5g/升碳酸钠和50g/升硫酸钠存在下，用2％和下式所示黄色染料
和3％下式所示绿松石蓝染料(见DE—A—1179317)
在60℃将对比例纤维染色60分钟。
染色后，纤维呈中等色调的绿色。
染色方法2(活性染料)：
使用相同的方法，不添加碱和盐将纤维染色。
染色后，实施例1和2的纤维比染色方法1中得到的绿色调深。对比例的纤维没有染上任何染料。
染色方法3(酸性染料)
在浴比为25∶1下，用1％下式所示黄色染料C.I.酸性黄1.7(C.I.No.18965)
和2％下式所示蓝色染料C.I.酸性蓝40(C.I.No.62125)在2％浓度为60％的乙酸的存在下，在98℃将纤维染色60分钟。实施例1和2的纤维变蓝，而对比例的纤维未染上颜色。
Claims (11)
1.向纤维素溶液中加入改性剂并从该溶液中纺丝、或者向粘胶溶液中加入改性剂并用粘胶纺丝方法纺丝得到的改性纤维素纤维，其中，所述改性剂是具有伯、仲或叔胺侧基并且分子量大于1000的聚合胺化合物。
2.根据权利要求1的改性纤维素纤维，其中，所述聚合胺化合物的分子量大于20,000，优选大于50,000。
3.根据权利要求1或2的改性纤维素纤维，其中，所述聚合胺化合物包括下式(1)、(2)和(3)所示的结构单元或它们的组合：
(1)(2)
(3)
式中：
R1和R2是相同的或不同的，每个表示氢原子，C1—C4烷基，未取代的苯基或被选自C1—C4烷基、C1—C4烷氧基或卤原子、优选氟、氯和溴原子的至多3个取代基取代的苯基；
R3是氢原子，甲基或乙基；
R4是氢原子，甲基或乙基；
m为1至4；和
O为0至4。
4.根据权利要求1至3中至少一项要求的改性纤维素纤维，其中，R1和R2可相同或不同，每个表示氢原子、甲基或乙基，m为1至2，以及O为0至2。
5.根据权利要求1至4中至少一项要求的改性纤维素纤维，其中，所述聚合胺化合物为聚乙烯基胺。
6.根据权利要求1至5中至少一项要求的改性纤维素纤维，其中，基于使用的纺丝原液中的纤维素含量，改性剂的吸留量为0.1％—10％重量，优选为0.3％—3％重量。
7.根据权利要求1至6中至少一项要求的改性纤维素纤维，其中，用粘胶纺丝法进行纺丝。
8.根据权利要求1至6中至少一项要求的改性纤维素纤维，其中，用库普罗方法(cupro process)或利阿塞尔方法(lyocell process)进行纺丝。
9.用水溶性织物染料染色和印花纤维材料的方法，它包括，用不添加电解质盐和碱的染料溶液和权利要求1—8中至少一项要求的改性纤维素纤维进行染色。
10.根据权利要求9的方法，其中，所述染料含有纤维活性基团。
11.权利要求1至8中的1项或多项要求的改性纤维素纤维的纺纱、纺织物或针织物。
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| DE2736147A1 (de) * | 1977-08-11 | 1979-02-22 | Hoechst Ag | Wasserdampfaufnahmefaehiger und wasserdampfdurchlaessiger klebstoff, ein verfahren zu seiner herstellung und seine verwendung |
| JPS61125880A (ja) * | 1984-11-22 | 1986-06-13 | Nippon Kayaku Co Ltd | 感熱記録材料 |
| SE452448B (sv) * | 1985-02-04 | 1987-11-30 | Hyco Hydraulic Ab | Lyftanordning for lyftning av fordon |
| JPS61258801A (ja) * | 1985-05-13 | 1986-11-17 | Nitto Boseki Co Ltd | カチオン性再生セルロ−ス製品の製造方法 |
| DE3709766A1 (de) * | 1987-03-25 | 1988-10-06 | Hoechst Ag | Verfahren zum alkali-freien faerben mit reaktivfarbstoffen |
| DE3831464A1 (de) * | 1988-09-16 | 1990-03-29 | Hoechst Ag | Verfahren zum alkali-freien faerben und bedrucken von cellulosefasern |
| TW223134B (zh) * | 1991-05-11 | 1994-05-01 | Hoechst Ag | |
| TW211595B (zh) * | 1991-12-07 | 1993-08-21 | Hoechst Ag |
-
1994
- 1994-06-30 DE DE4422864A patent/DE4422864A1/de not_active Withdrawn
-
1995
- 1995-06-07 US US08/482,032 patent/US5529585A/en not_active Expired - Fee Related
- 1995-06-19 DE DE59505629T patent/DE59505629D1/de not_active Expired - Fee Related
- 1995-06-19 AT AT95109424T patent/ATE178956T1/de not_active IP Right Cessation
- 1995-06-19 ES ES95109424T patent/ES2133619T3/es not_active Expired - Lifetime
- 1995-06-19 DK DK95109424T patent/DK0692559T3/da active
- 1995-06-19 EP EP95109424A patent/EP0692559B1/de not_active Expired - Lifetime
- 1995-06-28 CN CN95108112A patent/CN1124306A/zh active Pending
- 1995-06-28 FI FI953196A patent/FI110191B/fi active
- 1995-06-28 TR TR95/00769A patent/TR199500769A1/xx unknown
- 1995-06-29 CA CA002152978A patent/CA2152978A1/en not_active Abandoned
- 1995-06-29 JP JP16423695A patent/JP3622928B2/ja not_active Expired - Fee Related
- 1995-06-29 KR KR1019950018099A patent/KR960001220A/ko not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1089816C (zh) * | 1997-07-14 | 2002-08-28 | 阿克佐诺贝尔公司 | 两性表面活性剂作为粘胶纺丝浴添加剂的应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| FI953196A0 (fi) | 1995-06-28 |
| JP3622928B2 (ja) | 2005-02-23 |
| DE59505629D1 (de) | 1999-05-20 |
| US5529585A (en) | 1996-06-25 |
| EP0692559B1 (de) | 1999-04-14 |
| ATE178956T1 (de) | 1999-04-15 |
| DE4422864A1 (de) | 1996-01-04 |
| CA2152978A1 (en) | 1995-12-31 |
| KR960001220A (ko) | 1996-01-25 |
| FI953196A (fi) | 1995-12-31 |
| JPH08109514A (ja) | 1996-04-30 |
| ES2133619T3 (es) | 1999-09-16 |
| FI110191B (fi) | 2002-12-13 |
| DK0692559T3 (da) | 1999-10-25 |
| EP0692559A1 (de) | 1996-01-17 |
| TR199500769A1 (tr) | 1996-10-21 |
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