CN1040211A - 低粘度环氧树脂组合物 - Google Patents
低粘度环氧树脂组合物 Download PDFInfo
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Abstract
通过加入一种活性稀释剂(包括芳族乙烯基单体),而将有1,2环氧基团并且每分子具有至少两个环氧基团的环氧树脂和有效量硬化剂的无溶剂环氧树脂组合物的粘度明显降低,因而它们适用于减压浸渍、预浸电绝缘材料和结构复合材料。
Description
本发明通常是涉及环氧树脂技术,更具体地讲是涉及新型环氧树脂组合物,该组合物在电绝缘复合材料以及其它要求完全电绝缘的低粘度树脂的应用方面具有特殊的用途。
在电气设备的制造中,是以用可固化的聚合物材料浸渍的玻璃纤维织物、热塑性薄膜和云母纸或云母片带的形式达到电绝缘的。该织物薄膜、纸或带或其它适用的形式或者在应用于导体以前用聚合物材料处理,即预浸,或者在以后采用用于生产电机和发电机用线圈的减压浸渍技术。在任何情况下,必须使用该树脂组合物并且必须在没有空隙的情况下进行固化,这些空隙会由于在电压下的击穿而降低绝缘物的使用寿命。为此,该树脂组合物实际上必须是无溶剂的,并且同时它必须具有相对较低的粘度,以便易于在线圈的绝缘带的周围和之间流动,而且在预浸材料的制备中同样地达到有效的浸透。而对于制备预浸绝缘物来说,相对较低的粘度并不关键,因为可以提高浸渍温度以降低粘度。但是在这样高的温度下容易发生反应和凝胶化,这就使得某些其它理想的高粘度组合物不能用于预浸绝缘。
由于环氧树脂显著的优越性能:热稳定性、粘合性、拉伸、挠曲和压缩强度、抗溶剂、抗油、抗酸和抗碱性,因此它们通常优于聚酯树脂。然而,这些树脂的粘度一般约为6500~15000厘泊(CPS)。此外,当在这些树脂中加入某些常用的硬化剂时,它们的粘度增至约10000至30000CPS,这对于有效的浸渍操作来说是太高了。许多高性能的树脂如可溶酚醛环氧树脂或可溶甲酚醛环氧树脂在室温下是固体或基本上是固体,因而它们通常需要加入溶剂,以便以液体形式使用。虽然通过使用某些环氧稀释剂可大大降低高粘度,但采用该方法的先有研究工作已造成了改性组合物的热稳定性降低以及降低了固化树脂的电性能和机械性能。
基于下述我的惊人发现,现在可以提供一些在减压浸渍操作中具有特殊用途的环氧树脂组合物,这是由于它们的热稳定性好而且在25℃下的粘度低(低于3000CPS,在某些情况下甚至低于1000CPS)。现在还可以提供一些在预浸绝缘物的制备中具有特殊用途的环氧树脂组合物,这是因为它们在为将其粘度降低到有效渗透和浸渍所需的水平而必须加热到的高温下的热定性好。本发明的这些环氧树脂组合物可用于含有树脂和增强材料如玻璃或碳纤维的复合材料,因为用低粘度的树脂容易浸润增强材料。此外,可以始终地获得这些新的结果而不会带来任何偏离和不利情况,例如对环氧树脂的电性能和机械性能的不利影响。
如上所述,本发明集中于我的出人意料的发现,即有某些稀释材料,它们不像那些以前试图解决该问题而使用但未成功的稀释剂如环氧稀释剂,它们不会降低热稳定性及任何其它重要的性能。具体说我已证实,活性稀释剂苯乙烯、α-甲基苯乙烯、乙烯基甲苯、叔丁基苯乙烯、二乙烯基苯、二异丙烯基苯及其混合物能够产生本发明的这些新的且重要的结果和优点。乙烯基甲苯是指间甲基苯乙烯和对甲基苯乙烯异构体的混合物,但也可以使用单个异构体如对甲基苯乙烯。类似地,叔丁基苯乙烯是指对叔丁基苯乙烯或邻位、间位和对位异构体的混合物。二乙烯基苯和二异丙烯基苯也是指一种异构体或邻位、间位和对位异构体的混合物。此外,二乙烯基苯也可以含有相当量的乙基乙烯基苯,二乙烯基苯的一般分析是57%二乙烯基苯和38%乙基乙烯基苯。我还发现当以整个组合物的3%~33%的用量单独使用或与环氧树脂材料组成混合物一起使用这些特定的稀释剂时,一样能够得到这些新的结果和优点。
本发明还基于苯乙烯和其它芳族乙烯基单体与环氧树脂的阴离子或阳离子聚合的新概念,该聚合于咪唑、三氟化硼一胺或三氯化硼-胺配合物的存在下进行。环氧树脂和苯乙烯或其它芳族乙烯基单体是采用1986年7月29日颁布的美国专利4,603,182中所述的有机金属催化剂和酚类加速剂进行阳离子聚合的。该专利所公开的内容在此列入作为参考。
本发明包括所述的出人意料的发现,即苯乙烯和其它乙烯基单体采用咪唑化合物作为硬化剂与环氧树脂进行阴离子聚合。如果三氟化硼-胺或三氯化硼-胺配合物的胺组分是活性物,则该聚合反应是阴离子的,而如果活性物是三氟化硼或三氯化硼,则该聚合物反应是阳离子的。
在先有技术中,苯乙烯作为活性稀释剂的应用包括一种用于苯乙烯自由基聚合反应的过氧化物催化剂和一种单独的用于环氧固化的硬化剂和催化剂。对于环氧化物和苯乙烯,本发明仅用一种硬化剂,并且不包括自由基聚合。此外,不像先有技术是用苯乙烯作为与马来酐预反应的改性环氧树脂的稀释剂并采用易于加速和增大粘度增长的过氧化物催化的自由基反应,本发明的组合物不含有过氧化物或酸酐。环氧树脂中的酸酐易于受潮水解而形成多酸并进一步降低储存稳定寿命。
本专业的技术人员将理解,除减压浸渍树脂和用于制备电绝缘预浸料坯的树脂外,还可以应用这个新的化学法,并且那些应用包括用于制备树脂-玻璃层合物涂层、模塑和铸封料,制模等的环氧和聚酯类的热固性树脂。
那么,广泛和概括地来说,本发明是一种具有优异热稳定性的热固性树脂组合物,它主要包括约50%~95%的1,2环氧树脂(其每分子具有至少两个环氧基团),约3%~33%的选自上述的活性稀释剂,并包含少量但是有效量的咪唑化合物、三氟化硼-胺配合物或三氯化硼-胺配合物。
如上所述,有较多种的材料可供选择用于实施本发明。因此,通过使用上述一般类型混合物的任何热固性环氧树脂,通常始终可得到这些新的结果和优点。所包括的那些适于实施本发明或特别理想的是双酚A二环氧甘油醚环氧树脂(例如由壳牌化学公司销售的那些商标为EPON826和EPON828的环氧树脂)。还包括该结构式的其它液体树脂(例如由道化学公司销售的那些商标为DER330、331和332的环氧树脂,Celanese公司的Epi-Rez 508、509和510,Ciba-Geigy的Araldite 6004、6005和6010)。该类型的其它合适的树脂是可溶酚醛环氧树脂(例如道化学公司的DEN 431和DEN 438以及Celanese公司的Epi-Rez SU-2.5)、环氧可溶甲酚醛树脂(例如Ciba-Geigy销售的商品ECN1235、1273和1299)、卤代环氧树脂(例如Ciba-Geigy的Araldite8061)和环脂族环氧树脂(例如联合碳化物公司的ERL4206、4221、4221E、4234、4090和4289以及Ciba-Geigy的Araldite CY 182和183)。
用于该环氧树脂或这类树脂混合物的硬化剂包括咪唑、1-甲基咪唑、2-甲基咪唑、1,2-二甲基咪唑、2-乙基咪唑、1-氰乙基-2-乙基-4-甲基咪唑、2-苯基咪唑、2,4-二甲基咪唑、2-乙基-4-甲基咪唑、2-+-烷基咪唑、2-+七烷基咪唑、1-苄基-2-甲基咪唑及其它咪唑衍生物。含有咪唑类的该组合物在被加热到约80~100℃时快速固化,但它们的贮存期在室温下通常少于约2~4周。当需要较长的贮存期稳定性时,较理想的硬化剂是三氟化硼-单乙胺或三氯化硼-胺配合物例如,Ciba-Geigy的产品DY9577,它将使该化合物在室温下的适用期增加到约2个月。所述硬化剂含量的比例可以为每100份(重量)环氧-稀释剂组合物约含1~10份(重量),最好为约2~6份(重量)。
降低环氧树脂和硬化剂的热固性组合物粘度的活性稀释剂将在混合物各组分的混合工序中由操作者选择的时候加入,并且该活性稀释剂将是我已发现在这方面特别有效的那些特定化合物中的一种或另一种或其混合物。为了产生始终达到本发明新的结果和优点所必需的惊人的粘度降低效应,苯乙烯,α-甲基苯乙烯,乙烯基甲苯、叔丁基苯乙烯、二乙烯基苯和二异丙烯基苯的异构体或异构体的混合物,及其混合物,尤其是本发明选择的化合物范围。在本发明混合物中,该活性稀释剂或活性稀释剂的混合物的用量占整个组合物的约3%~33%,我的进一步发现是,在此范围内可以获得这些新的结果和优点,而在此范围之外,则或者不能始终一致地获得这些结果,或者对另一种性质产生不利影响,特别是在该范围的高端更是如此。
通过本发明下列说明性的但不是限制性的实例,本专业的技术人员将对本发明及其新的结果和优点有进一步的和更好的理解,因为它实际上已进行了实验。
实例1
通过向其中加入10%乙烯基甲苯,将EPON828环氧树脂的粘度(25℃)由近似13,000cps降低到约1,200cps。当该粘度降低的环氧树脂在60~100℃下用每100份(重量)90/10EPON828/乙烯基甲苯溶液含5.0或10.0份(重量)2-乙基-4-甲基咪唑或1,2-二甲基咪唑的溶液固化时,形成一种亮琥珀色的靱性固体。
使用ASTM测试方法D628-72,在160℃固化3,0小时后,在264psi下的热挠曲温度,对于含5.0份(重量)2-乙基-4-甲基咪唑的树脂是92℃,而对于含5.0份(重量)1,2-二甲基咪唑的树脂是94℃。
实例2
可溶酚醛DEN438环氧树脂在室温下基本上是固体。由85份(重量)DEN438和15份(重量)乙烯基甲苯组成的溶液在室温下是可流动的液体。由DEN438〔85份(重量)〕和乙烯基甲苯〔15份(重量)〕制成的无溶剂树脂用3.0份(重量)2-乙基-4-甲基咪唑固化成一种亮琥珀色的靱性固体,在160℃下固化4小时后其热挠曲温度为155℃。如果用1,2-二甲基咪唑代替2-乙基-4-甲基咪唑,则其HDT为144℃。
实例3
由80份(重量)几乎固体的DEN438可溶酚醛环氧树脂与20份(重量)乙烯基甲苯制成粘度近似为5,000CPS的树脂。该树脂溶液〔100份(重量)〕用3.0份(重量)EMI-24催化。该树脂在160℃下固化4小时,形成一种亮琥珀色的靱性固体,其热挠曲温度为138℃。
实例4
通过在90.0份(重量)EPON826环氧树脂中加入10.0份(重量)乙烯基甲苯而将该树脂的粘度由近似8,000cps降低到1,000cps。该环氧-乙烯基甲苯树脂〔100份(重量)〕用2.7份(重量)2-乙基-4-甲基咪唑催化并在150℃下固化15小时。热挠曲温度为139℃。一个重10克、直径为2.5英寸的该固化树脂的盘在160℃下老化72小时后没有重量变化,这表明乙烯基甲苯已完全反应。
用EPON826〔90.0份(重量)〕与乙烯基甲苯〔10.0份(重量)〕和三亚乙基四胺〔12.6份(重量)〕进行类似的测试,其热挠曲温度为106℃。如果在160℃下固化72小时,则固化的盘式样品失重,这表明存在有未反应的乙烯基甲苯。
实例5
通过向85.0份(重量)环氧树脂中加入15.0份(重量)乙烯基甲苯将EPON826环氧树脂的粘度由近似8,000cps降低到400Cps。该环氧-乙烯基甲苯树脂〔100份(重量)〕用2.6份(重量)2-乙基-4-甲基咪唑催化并在150℃下固化15小时。热挠曲温度为135℃。如果在160℃下老化72小时,则固化的环氧树脂的盘式样品没有失重,这表明不存在任何游离的(未反应的)乙烯基甲苯。
用EPON826树脂〔85.0份(重量)〕与乙烯基甲苯〔15.0份(重量)〕和三亚乙基四胺〔11.9份(重量)〕进行类似的测试,在150℃下固化15小时后,热挠曲温度为104℃。固化的盘式样品在160℃下老化72小时,产生明显的失重,这表明有未反应的乙烯基甲苯存在。
实例6
由EPON826环氧树脂〔100份(重量)〕和2-乙基-4-甲基咪唑〔3.0份(重量)〕制得№6A树脂样品。№6B树脂样品由EPON826环氧树脂〔100份(重量)〕与乙烯基甲苯〔18.2份(重量)〕和2-乙基-4-甲基咪唑(3.0份(重量)〕制得。每个样品在不同温度即200℃、220℃和230℃下老化84天后,为测定其热稳定性比较这些样品的失重百分比。在260℃下老化14天后也进行比较。用于热稳定性测定的每个试样的样品都是重10克、直径为2.5英寸的盘。相应的失重如下:
失重百分比
84天 84天 84天 14天
试样 @200℃ @220℃ @230℃ @260℃
No.6A 3.88 5.16 8.43 14.68
No.6B 3.83 4.78 7.04 8.52
该比较测定表明,包含15%乙烯基甲苯的样品(№6B试样)失重较少。这证明由于加入乙烯基甲苯而改进了热稳定性。与此相反,使用常用的环氧稀释剂如丁基缩水甘油醚或苯基缩水甘油醚来降低粘度,相对于粘度较高、未改性的环氧树脂来说,热稳定性会降低。
实例7
因为需要加热DEN438树脂来降低其粘度,所以难以制备DEN438可溶酚醛环氧树脂〔100份(重量)〕与2-乙基-4-甲基咪唑〔3.0份(重量)〕的热稳定性测试试样。当用2-乙基-4-甲基咪唑催化该热的环氧树脂时,加热会造成凝胶化。然而,如果用15%或20%的乙烯基甲苯稀释该DEN438环氧树脂,则形成一种在室温下易于处理的液体。用于测试热稳定性的盘式样品由DEN438树脂与15%乙烯基甲苯(№7A)或20%乙烯基甲苯(№7B)的试样进行制备。№7A的试样组合物由DEN438环氧树脂〔100.0份(重量)〕、乙烯基甲苯〔18.2份(重量)〕和2-乙基-4-甲基咪唑〔3.0份(重量)〕组成,而№7B试样由DEN438树脂〔100份(重量)〕、乙烯基甲苯〔25.8份(重量)〕和2-乙基-4-甲基咪唑〔3.0份(重量)〕组成。相应的失重如下:
失重百分比
84天 84天 84天 14天
试样 @200℃ @220℃ @230℃ @260℃
No.7A 1.77 3.35 6.88 9.28
No.7B 1.68 2.93 6.21 8.44
该热稳定性测试表明,将乙烯基甲苯的含量由15%增至20%,则热稳定性有所改进。这个现象也与使用常规环氧稀释剂的结果相反,因为常规的环氧稀释剂随着其用量的增加将促使热稳定性的降低。
实例8
可溶甲酚醛环氧树脂ECN1235和三氟化硼-单乙胺的粘度太高,不便于用来制备无溶剂预浸料坯。而ECN1235〔80份(重量)〕、苯乙烯〔20.0份(重量)〕和三氟化硼-单乙胺的树脂组合物适用于该用途,因为苯乙烯将该组合物的粘度降低到了在50~60℃下易于浸渍的程度。在160℃下固化10小时后,该组合物的损耗因数(60Hz和10伏/密尔)在125℃和150℃下分别为0.018和0.10。
实例9
将几乎为固体的可溶酚醛环氧树脂DEN438用苯乙烯稀释并用三氟化硼-单乙胺催化,形成一种在室温下具有优异贮存期稳定性的液体树脂组合物。将由DEN438〔(100.0份(重量)〕、苯乙烯〔30.0份(重量)〕和三氟化硼-单乙胺〔4.0份(重量)〕组成的树脂组合物在160℃下固化15小时,其在100℃、125℃和150℃下的损耗因数(60Hz,10伏/密尔)分别为0.016、0.041和0.22。该组合物的热挠曲温度为179℃。
实例10
由几乎为固体的可溶酚醛环氧树脂DEN438〔(85.0份(重量)〕、乙烯基甲苯〔15.0份(重量)〕和三氯化硼-胺化合物DY9577〔5.0份(重量)〕制备一种液体树脂。将该液体树脂组合物固化成一种硬的、亮琥珀色的韧性固体。
在该说明书和所附的权利要求书中,所述的无论是百分比或比例,除非特意表明,都是指重量。
已依据合适的法令要求对本发明进行了如此描述,我说明,我要求通过颁布专利保护的内容限定于权利要求书中。
Claims (12)
1、一种具有优异热稳定性的热固性树脂组合物,它包括约50%~95%(重量)的每分子具有至少两个环氧基团的1,2环氧树脂,约3%~33%(重量)的含有一种芳族乙烯基单体的活性稀释剂以及每100份(重量)环氧树脂和活性稀释剂中约含1~10份(重量)选自咪唑化合物、三氟化硼一胺和三氯化硼一胺及其混合物的含氮的有机催化硬化剂。
2、根据权利要求1所述的热固性树脂组合物,其中所述的咪唑化合物催化硬化剂选自咪唑、1-甲基咪唑、2-甲基咪唑、1,2-二甲基咪唑、2-乙基咪唑、1-氰乙基-2-乙基-4-甲基咪唑、2-苯基咪唑、2,4-二甲基咪唑、2-乙基-4-甲基咪唑、2-+-烷基咪唑、2-+七烷基咪唑和1-苄基-2-甲基咪唑及其混合物。
3、根据权利要求1所述的热固性树脂组合物,其中环氧树脂占约50%~95%(重量),而芳族乙烯基单体活性稀释剂占约3%~33%(重量),与此组合的含氮的有机催化硬化剂的量为每100份(重量)环氧树脂和活性稀释剂中约含2~6份(重量)的上述硬化剂。
4、根据权利要求1所述的热固性树脂组合物,其中所述的活性稀释剂是乙烯基甲苯。
5、一种具有优异热稳定性的热固性树脂组合物,它包括约50%~95%(重量)的每分子具有至少两个环氧基团的1,2环氧树脂、约3%~33%(重量)的含有一种芳族乙烯基单体的活性稀释剂以及每100份(重量)环氧树脂和活性稀释剂中约含1~10份(重量)咪唑化合物催化硬化剂。
6、根据权利要求5所述的热固性树脂组合物,其中每100份(重量)环氧树脂和活性稀释剂中约含2~6份(重量)所述咪唑化合物催化硬化剂。
7、根据权利要求5所述的热固性树脂组合物,其中所述咪唑化合物催化硬化剂选自咪唑、1-甲基咪唑、2-甲基咪唑、1,2-二甲基咪唑、2-乙基咪唑、1-氰乙基-2-乙基-4-甲基咪唑、2-苯基咪唑、2,4-二甲基咪唑、2-乙基-4-甲基咪唑、2-+-烷基咪唑、2-+七烷基咪唑和1-苄基-2-甲基咪唑及其混合物。
8、根据权利要求5所述的热固性树脂组合物,其中所述的活性稀释剂是乙烯基甲苯。
9、根据权利要求5所述的热固性树脂组合物,其中所述的催化硬化剂包含2-乙基-4-甲基咪唑。
10、一种具有优异热稳定性的热固性树脂组合物,它包括约50%~95%的每分子具有至少两个环氧基团的1,2环氧树脂、约3%~33%(重量)的含有一种芳族乙烯基单体的活性稀释剂以及每100份(重量)环氧树脂和活性稀释剂中约含1~10份(重量)选自三氟化硼-胺和三氯化硼-胺及其混合物的胺催化硬化剂。
11、根据权利要求10所述的热固性树脂组合物,其中每100份(重量)环氧树脂和活性稀释剂中约含2~6份(重量)所述的胺催化硬化剂。
12、根据权利要求10所述的热固性树脂组合物,其中所述的活性稀释剂是乙烯基甲苯。
Priority Applications (1)
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CN89106130A CN1040211A (zh) | 1984-10-05 | 1989-07-26 | 低粘度环氧树脂组合物 |
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US06/658,102 US4603182A (en) | 1984-10-05 | 1984-10-05 | Low viscosity epoxy resin compositions |
CN89106130A CN1040211A (zh) | 1984-10-05 | 1989-07-26 | 低粘度环氧树脂组合物 |
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CN1040211A true CN1040211A (zh) | 1990-03-07 |
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CN89106130A Pending CN1040211A (zh) | 1984-10-05 | 1989-07-26 | 低粘度环氧树脂组合物 |
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US (2) | US4603182A (zh) |
JP (1) | JPH0618855B2 (zh) |
KR (1) | KR930002943B1 (zh) |
CN (1) | CN1040211A (zh) |
CA (1) | CA1233295A (zh) |
CH (1) | CH667662A5 (zh) |
DE (1) | DE3534782A1 (zh) |
FR (1) | FR2571378B1 (zh) |
GB (1) | GB2165251B (zh) |
IT (1) | IT1188194B (zh) |
NL (1) | NL8502703A (zh) |
NO (1) | NO167042C (zh) |
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-
1984
- 1984-10-05 US US06/658,102 patent/US4603182A/en not_active Expired - Lifetime
-
1985
- 1985-02-01 CA CA000473385A patent/CA1233295A/en not_active Expired
- 1985-09-18 GB GB08523062A patent/GB2165251B/en not_active Expired
- 1985-09-30 DE DE19853534782 patent/DE3534782A1/de not_active Withdrawn
- 1985-10-01 CH CH4226/85A patent/CH667662A5/de not_active IP Right Cessation
- 1985-10-01 FR FR858514506A patent/FR2571378B1/fr not_active Expired
- 1985-10-03 NL NL8502703A patent/NL8502703A/nl active Search and Examination
- 1985-10-03 JP JP60219296A patent/JPH0618855B2/ja not_active Expired - Fee Related
- 1985-10-04 IT IT22363/85A patent/IT1188194B/it active
- 1985-10-04 KR KR1019850007297A patent/KR930002943B1/ko not_active IP Right Cessation
- 1985-10-04 NO NO853934A patent/NO167042C/no not_active IP Right Cessation
-
1986
- 1986-02-25 US US06/833,303 patent/US4656090A/en not_active Expired - Lifetime
-
1989
- 1989-07-26 CN CN89106130A patent/CN1040211A/zh active Pending
Cited By (8)
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CN1062288C (zh) * | 1996-12-18 | 2001-02-21 | 閎邦实业股份有限公司 | 用于绝缘涂装电容器的单液型环氧树脂浸剂 |
CN100503690C (zh) * | 2005-12-28 | 2009-06-24 | 同济大学 | 一种可用于氰酸酯固化反应的双组分催化剂及其制备方法 |
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CN112151206A (zh) * | 2020-09-25 | 2020-12-29 | 国网河南省电力公司周口供电公司 | 一种碳纤维复合芯导线及其制备方法 |
CN112151206B (zh) * | 2020-09-25 | 2022-07-01 | 国网河南省电力公司周口供电公司 | 一种碳纤维复合芯导线及其制备方法 |
CN115386351A (zh) * | 2022-07-29 | 2022-11-25 | 西安众海石油科技有限公司 | 一种缓凝高强树脂及其制备方法 |
CN115386351B (zh) * | 2022-07-29 | 2024-02-27 | 西安众海石油科技有限公司 | 一种缓凝高强树脂及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
JPH0618855B2 (ja) | 1994-03-16 |
GB2165251A (en) | 1986-04-09 |
US4603182A (en) | 1986-07-29 |
KR930002943B1 (ko) | 1993-04-15 |
CH667662A5 (de) | 1988-10-31 |
FR2571378A1 (fr) | 1986-04-11 |
CA1233295A (en) | 1988-02-23 |
NO853934L (no) | 1986-04-07 |
KR860003626A (ko) | 1986-05-28 |
NO167042C (no) | 1991-09-25 |
FR2571378B1 (fr) | 1989-09-08 |
GB2165251B (en) | 1988-02-03 |
NO167042B (no) | 1991-06-17 |
DE3534782A1 (de) | 1986-05-15 |
NL8502703A (nl) | 1986-05-01 |
US4656090A (en) | 1987-04-07 |
GB8523062D0 (en) | 1985-10-23 |
IT8522363A0 (it) | 1985-10-04 |
JPS61106619A (ja) | 1986-05-24 |
IT1188194B (it) | 1988-01-07 |
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