CN1295599A - 阻燃聚碳酸酯树脂/abs接枝共聚物的共混物 - Google Patents
阻燃聚碳酸酯树脂/abs接枝共聚物的共混物 Download PDFInfo
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- CN1295599A CN1295599A CN99804707A CN99804707A CN1295599A CN 1295599 A CN1295599 A CN 1295599A CN 99804707 A CN99804707 A CN 99804707A CN 99804707 A CN99804707 A CN 99804707A CN 1295599 A CN1295599 A CN 1295599A
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Abstract
一种含有芳香碳酸酯树脂的热塑性树脂组合物,一种包括分散在连续刚性热塑性相中的非连续橡胶相的橡胶改性接枝共聚物,其中至少一部分刚性热塑性树脂被化学接枝到橡胶相中,其中该共聚物的橡胶相在(C30－C108)多元酸表面活性剂存在下,通过水相乳液聚合制备,和一定阻燃量的有机磷阻燃剂。
Description
发明领域
本发明涉及具有改进性能的阻燃聚碳酸酯树脂/ABS接枝共聚物的共混物。
相关技术简述
众所周知，含有芳香族聚碳酸酯树脂、ABS接枝共聚物、含氟聚合物和有机磷酸酯阻燃剂的，阻燃热塑性树脂组合物已为大家所知，并已经发现组合物具有优良的阻燃性和优良的耐热性，例如见已转让的美国专利No.5,204,394。
阻燃树脂组合物要求具有低熔融粘度并具有改进的美学外观，尤其是具有改进的抗条纹性和改进的物理性能，对于所制模塑制品，尤其具有改进的抗边缘破裂性能。
发明概述
本发明中的热塑性树脂组合物，包括：
(a)一种芳香族聚碳酸酯树脂，
(b)一种包括分散在连续刚性热塑性相中的非连续橡胶相的橡胶改性接枝共聚物，其中至少一部分刚性热塑性相被化学接枝到橡胶相上，所说的橡胶改性接枝共聚物通过一种水相乳液聚合方法制备，其中使用一种(C30-C108)多元酸表面活性剂，和
(c)一定阻燃量的有机磷酸酯阻燃剂；
本发明中的组合物赋予了由其模塑的制品改进的流动特性、改进的美学外观，尤其是改进的抗开裂(splay)和条纹性，和改进的物理性能，特别是改进的抗边缘破裂性。
发明详述
在一种优选的实施方案中，本发明的热塑性树脂组合物包括：以100份重量份(pbw)的热塑性树脂组合物计算，40-95pbw、进一步优选50-90pbw、更进一步优选55-80pbw的芳香族聚碳酸酯树脂，4-59pbw、进一步优选8-48pbw、更进一步优选14-39pbw橡胶改性接枝共聚物，及1-20pbw、进一步优选2-15pbw，更进一步优选6-12pbw的有机磷酸酯阻燃剂，。
芳香族聚碳酸酯树脂适合用作本发明的热塑性树脂组合物中聚碳酸酯树脂组分是大家所熟知的，该化合物的制备和性能已经在美国专利No.3,169,121，4,487,896和5,411,999中概述，其相关的内容在这里可作为参考。
在一种优选的实施方案中，本发明中的芳香族聚碳酸酯树脂组分是结构式为(Ⅰ)的二元酚与碳酸酯母体的反应产物：
HO-A-OH (Ⅰ)
其中A是一种二价芳基，
该芳香族聚碳酸酯树脂组分含有通式(Ⅱ)的结构单元：其中A同上面定义。
这里所使用的，术语“二价芳基”包括：那些含有一个芳环如亚苯基的二价基团，那些含有缩合芳环体系如萘的二价基团，那些含有两个或多个由非芳烃键如烷撑、烷叉或磺酰基连接的芳环的二价基团。芳环上的一个或多个位置上的任何一种基团均可被如一种卤素基团或(C1-C6)烷基取代。
在一种优选的实施方案中，A是一种二价芳基，其结构式为(Ⅲ)：
合适的二元酚包括，例如，一种或多种2，2-二-(4-羟基苯基)丙烷(“双酚A”)、2，2-二-(3，5-二甲基-4-羟基苯基)丙烷、二-(4-羟基苯基)甲烷、4，4-二-(4-羟基苯基)庚烷、3，5，3’，5’-四氯-(4，4’-二-羟基苯基)丙烷、2，6-二羟基萘、氢醌、2，4’-二羟基苯基砜。在高度优选的实施方案中，二元酚是双酚A。
碳酸酯母体是一种或多种羰基卤化物、碳酸酯或卤代甲酸酯，合适的羰基卤化物包括，如羰基溴化物和羰基氯化物；合适的碳酸酯包括，例如碳酸二苯酯、碳酸二氯苯酯、碳酸二萘基酯、碳酸苯基甲苯酯和碳酸二甲苯酯。合适的卤代甲酸酯包括，如一种二元酚的二卤代甲酸酯，例如氢醌或乙二醇类，如乙二醇、新戊二醇。在高度优选的实施方案中，碳酸酯母体是碳酰氯。
合适的芳香族聚碳酸酯树脂包括线性芳香族聚碳酸酯树脂、支化芳香族聚碳酸酯。合适的线性芳香族聚碳酸酯包括，例如双酚A聚碳酸酯树脂。合适支化聚碳酸酯是熟知的通过一种多官能团的芳香化合物与一种二元酚及一种碳酸酯母体反应形成支化聚合物而制得，通常参见美国专利No.3,544,514、3,635,895和4,001,184，专利中的相关内容在此引入作为参考。多官能团化合物通常是芳香族的且含有至少3个如下官能团：羧基、羰酸酐、酚、卤代甲酸酯或它们的混合物，如1，1，1-三(4-羟苯基)乙烷、1，3，5-三羟基苯、1，2，4-苯三酸酐、1，2，4-苯三酸、1，2，4-苯三酰氯、4-氯仿基苯二酸酐、1，2，4，5-苯四酸、1，2，4，5-苯四酸二酐、苯六甲酸、苯六甲酸酐、1，2，5-苯三酸、苯酮四羧酸、苯酮四羧酸二酐。优选的多官能团芳香化合物是1，1，1-三(4-羟苯基)乙烷、1，2，4-苯三酸酐或1，2，4-苯三酸或它们的卤仿化衍生物。
在一种优选的实施方案中，本发明中的聚碳酸酯树脂组分是一种由双酚A和光气衍生出来的线性聚碳酸酯树脂。
在一种优选的实施方案中，聚碳酸酯树脂的重均分子量大约是10，000-200，000g/mol，重均分子量通过以聚苯乙烯为对照物的凝胶渗透色谱法测定的。这样的树脂通常在25℃、二氯甲烷中的特性粘度大约为0.3-1.5dl/g。
聚碳酸酯树脂通常由已知的方法制备，如界面聚合、酯交换法、溶液聚合或熔融聚合。
聚酯一碳酸酯的共聚酯树脂(copolyester-carbonate resins)也适用于本发明的芳香族聚碳酸酯树脂组分。适合用作本发明中热塑性树脂组合物中芳香族聚碳酸酯树脂组分的聚酯-碳酸酯的共聚酯树脂是众所周知的化合物，其制备和性能已经在美国专利No.3,169,121、4,430,484和4,487,896中概述，专利中的相关内容在此引入作为参考。
聚酯-碳酸酯的共聚酯树脂包括线性或无规支化聚合物，该聚合物链上含有重复碳酸酯基团、羧酸酯基团和芳香碳环基团，其中至少有一些碳酸酯基团直接键接到芳香碳环基团的环碳原子上。
在一种优选的实施方案中，本发明中的聚酯-碳酸酯的共聚酯树脂组分是由碳酸酯母体衍生出来的，至少一个二元酚及至少一个二元羧酸或同当量的二元羧酸。在一种优选的实施方案中，二元羧酸根据结构式(Ⅳ)选定的：
其中A＇是烷撑、烷叉、脂肪环的或芳基环的且优选一种非取代苯基或一种取代苯基，其中芳香环上的一个或多个位置被取代，其中每一个这样的取代基是独立的(C1-C6)烷基。而且聚酯-碳酸酯的共聚酯树脂包括具有上面通式(Ⅱ)的第一结构单元和通式(Ⅴ)的第二结构单元
其中A＇与前面定义相同。
合适的碳酸酯母体和二元酚是上面公开的那些。
合适的二元羧酸包括，例如苯二酸、异苯二酸、对苯二酸、二甲基对苯二酸、乙二酸(草酸)、丙二酸、丁二酸、戊二酸、己二酸、庚二酸、辛二酸、壬二酸、癸二酸、二甲基丙二酸、1，12十二烷二酸、顺式-1，4-环己烷二羧酸、反式-1，4-环己烷二羧酸、4，4’二苯甲酸、萘-2，6-二羧酸。合适的同当量二元羧酸包括，如前面公开的二元羧酸的酸酐、酯，或卤代衍生物，例如：苯二酸酐、对苯二甲酸二甲酯、丁二酰氯。
在一种优选的实施方案中，二元羧酸是一种芳香族二元羧酸，进一步优选一种或多种对苯二酸和间苯二酸。
在一种优选的实施方案中，在聚酯-碳酸酯的共聚酯树脂中的酯键与碳酸酯键之比是0.25-0.9。
在一种优选的实施方案中，聚酯-碳酸酯共聚物的重均分子量大约为10，000-200，000g/mol。
聚酯-碳酸酯的共聚酯树脂通常通过大家熟知的方法制备，例如界面聚合、酯交换法、溶液聚合或熔体聚合法。
适合于用作本发明中的橡胶改性热塑性树脂的橡胶改性热塑性树脂是通过一种本体聚合方法制备的，该树脂包括分散在连续刚性热塑性相中的非连续橡胶相，其中至少一部分刚性热塑性相被化学接枝到橡胶相中。
用于制备橡胶相的合适橡胶是那些玻璃化转变温度(Tg)小于或等于25℃的聚合物，进一步优选小于或等于0℃、甚至更优选小于或等于-30℃的聚合物。这里所指的聚合物Tg是通过用差示扫描量热法(加热速率20℃/min，Tg值由拐点确定)测定的。
在一种优选的实施方案中，橡胶包括具有一种或多种共轭二烯单体衍生的结构单元一种线性聚合物。
合适的共轭二烯单体包括，例如1，3-丁二烯、异戊二烯、1，3-庚二烯、甲基-1，3-戊二烯、2，3-二甲基丁二烯、2-乙基-1，3-戊二烯、1，3-己二烯、2，4-己二烯、二氯丁二烯、溴代丁二烯和二溴丁二烯及共轭二烯单体的混合物。在一种优选的实施方案中，共轭二烯单体是1，3-丁二烯。
橡胶可以选择包括由一种或多种可共聚的单烯类不饱和单体衍生的结构单元，其中不饱和单体选自(C2-C8)烯烃单体、乙烯基芳香单体和单烯类不饱和腈单体及(C1-C12)甲基丙烯酸烷基酯单体。
这里所使用的术语“(C2-C8)烯烃单体”指的是每个分子中含有2-8个碳原子及每个分子中含有一个乙烯类不饱和键的化合物。合适的(C2-C8)烯烃单体包括，例如，乙烯、丙烯、1-丁烯、1-戊烯、己烯。
合适的乙烯基芳香单体包括，例如苯乙烯和含有一个或多个连接到芳环上的烷基、烷氧基、羟基或卤代基的取代苯乙烯，包括，例如α-甲基苯乙烯、对甲基苯乙烯、乙烯基甲苯、乙烯基二甲苯、三甲基苯乙烯、丁基苯乙烯、氯代苯乙烯、二氯代苯乙烯、溴代苯乙烯、对羟基苯乙烯、甲氧基苯乙烯和乙烯基取代的缩合芳环结构，如乙烯基萘、乙烯基蒽、也可以是乙烯基芳香单体的混合物。
这里所使用的术语“单烯类不饱和腈单体”指的是一种无环化合物，该无环化合物每个分子中包括一个单腈基团和一个乙烯类不饱和单基且包括如丙烯腈、甲基丙烯腈和α-氯代丙烯腈。
这里所使用的术语“(C1-C12)烷基”指的是直链或支链取代基，该取代基每个含有1-12个碳原子，包括如甲基、乙基、正丁基、仲丁基、叔丁基、正丙基、异丙基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基和十二烷基。术语“(甲基)丙烯酸酯单体”统指丙烯酸酯类单体和甲基丙烯酸酯单体。合适的(C1-C12)(甲基)丙烯酸烷基酯单体包括(C1-C12)烷基丙烯酸酯单体，例如丙烯酸乙酯、丙烯酸丁酯、丙烯酸异戊基酯、丙烯酸正己基酯、丙烯酸2-乙基己基酯、及其(C1-C12)甲基丙烯酸烷基酯的类似物，例如甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸丙酯、甲基丙烯酸异丙酯、甲基丙烯酸丁酯、甲基丙烯酸己酯、甲基丙烯酸癸酯。
在首选实施方案中，橡胶是一种聚丁二烯均聚物。
在替代的优选实施方案中，橡胶是一种共聚物，优选一种嵌段共聚物，包括由一个或多个共轭二烯单体衍生的结构单元，最高为50wt％的结构单元，由选自乙烯基芳香单体和单烯类不饱和腈单体的一种或多种单体衍生而来，例如，苯乙烯-丁二烯共聚物、丙烯腈-丁二烯共聚物或苯乙烯-丁二烯-丙烯腈共聚物。
在一种高度优选的实施方案中，橡胶是苯乙烯-丁二烯嵌段共聚物，含有50-95wt％由丁二烯衍生的结构单元及5-50wt％由苯乙烯衍生的结构单元。
弹性相是在自由基引发剂、多元酸表面活性剂、任选，链转移剂存在的条件下，经水相乳液聚合制备而成，并凝聚成弹性相材料的粒子。
合适的引发剂包括常规的自由基引发剂例如，一种有机过氧化物化合物，如过氧化苯甲酰；过硫酸盐化合物，如过硫酸钾；偶氮腈类化合物，如2，2’-偶氮二-2，3，3三甲基丁腈；或氧化还原引发剂体系如氢过氧化异丙苯、硫酸亚铁、焦磷酸四钠、一种还原糖或甲醛化次硫酸钠。
合适的链转移剂包括，例如(C9-C13)烷基硫醇化合物，如壬基硫醇、叔十二烷基硫醇。
合适的多元酸表面活性剂包括多元羧酸的皂类，该多元羧酸的每个分子中含有30-108个碳原子，更进一步优选32-60个碳原子。
合适的多元羧酸可以通过含有乙烯键及链长为14-22个碳原子的脂肪酸二聚获得。合适的一元脂肪酸包括，例如油酸、反油酸、棕榈油酸、亚油酸、亚麻酸、十八碳三烯-4-酮酸、花生四烯酸、顺式13-二十二(碳)烯酸、4，7，11-二十二碳三烯-18-炔酸和9，11，13-十八碳三烯酸。在工业应用中这些酸的天然存在的混合物通常用于生产二聚脂肪酸。这种酸可以来源于如妥尔油脂肪酸、牛脂(动物油脂)脂肪酸及植物油，如黄豆、亚麻籽、棉籽和其他油类其由不饱和脂肪酸甘油酯构成。一般地，二聚是在高温下加热单体羧酸、有或没有催化剂存在下、并避免裂解及脱羧反应发生的条件下完成的。美国专利No.2,482,761、2,664,429、2,793,219、2,793,220、2,955,121、3,076,003、3,507,890、及3,925,342中还详细描述了二聚过程。
为了改进颜色，可以在后续反应步骤中通过加氢反应部分和全部饱和二聚脂肪酸，由Robert Johnson和Earle Fritz编写、MarcelDekker，Inc.NY.NY出版，“工业脂肪酸”一书中的第五章题目为“脂肪酸加氢”中详细进行了描述。合适的二聚酸在25℃下，尽管其数均分子量通常大于500g/mol，仍然保持是液体。
在一种优选的实施方案中，多元酸表面活性剂包括大于或等于50wt％的一种或多种脂肪酸二聚物和三聚物。被用于制备本发明新型组合物的二聚脂肪酸优选包括含有不大于约70％三元酸及具有很低非汁液(non-jucing)特性的不大于10％一元酸的一种产品。且优选以多元酸组分总重量计的一元羧酸含量不大于5wt％。以表面活性剂的总重量计时，二聚酸的含量优选至少为75wt％。需进一步重点指出的是在这些组合物中不包括松香酸、枞酸或它们的衍生物部分，因为这些作为枞酸的材料具有不理想的挥发性并可产生汁液。
优选的多元酸是无环脂族多元酸，环脂族多元酸和环芳香多元酸。多元酸优选含有30-108个碳原子的高分子量多元酸，并优选32-60个碳原子。优选的多元酸可溶于和/或相容于热塑性组合物中。
优选的含多元酸官能团的羧酸盐形式的多元酸是表面活性剂、乳化剂或皂类。
各种二聚脂肪酸市场上可以买得到，且这样的产品通常含有三聚脂肪酸，三聚脂肪酸是一元脂肪酸的3个分子通过聚合作为一种副产物形成的三元酸较高级的多元酸如四元羧酸(C72)和(C108)六元羧酸也可以存在。另外，商业化产品可以含有少量一元羧酸的异聚物或未反应的或全饱和单体的一元脂肪酸，该单体一元脂肪酸是因没有聚合或聚合过程完成后而未被去除留下的。
在一种优选的实施方案中，多元酸用于本发明橡胶改性接枝共聚物橡胶相的乳液聚合中，以100份丁二烯单体重量计，其数量为0.25-5wt％，进一步优选为0.75-3.5wt％，进一步优选1.5-2.75wt％。
在一种优选的实施方案中，橡胶是在一定量的链转移剂存在的条件下聚合得到的，该链转移催化剂能有效地提供甲苯中溶胀指数大于15的橡胶，进一步优选溶胀指数为20-150，且更进一步优选40-100。溶胀指数是在室温下，在大约96ml甲苯中，使约0.2g样品组合物的流延薄膜浸泡16小时测定的。溶胀指数等于溶胀样品的重量除以干样品的重量。
在一种优选的实施方案中，弹性相材料的乳液聚合粒子用光透射法测定的重均粒子大小为50-800纳米(nm)，进一步优选100-500nm。根据已知的方法，乳液聚合弹性粒子的大小可以任选通过乳液聚合粒子的力学的、胶体的或化学凝聚作用增大。
刚性热塑性树脂相包括一种或多种热塑性聚合物，其Tg大于25℃，优选大于或等于90℃，进一步优选大于或等于100℃。
在一种优选的实施方案中，刚性热塑性相包括由一种或多种选自(C1-C12)(甲基)丙烯酸烷基酯单体、乙烯基芳香单体或单烯类不饱和腈单体的一种或多种单体衍生的结构单元的聚合物。
合适的乙烯基芳香单体和单烯类不饱和腈单体及(C1-C12)(甲基)丙烯酸烷基酯单体是前面橡胶相描述中所陈述的那些单体。
在一种优选的实施方案中，刚性热塑性相包括一种乙烯基芳香聚合物，该聚合物含有来自一种或多种乙烯基芳香单体的第一结构单元，优选苯乙烯；和含有来自一种或多种单烯类不饱和腈单体的第二结构单元，优选丙烯腈。进一步优选，刚性相包括55-99wt％、更进一步优选60-90wt％由苯乙烯衍生的结构单元；和1-45wt％、更进一步优选10-40wt％由丙烯腈衍生的结构单元。
刚性热塑性相和橡胶相间产生的接枝量随着橡胶相的相对量和组成的变化而变化。在一种优选的实施方案中，10-90wt％、优选25-60wt％刚性热塑性相被化学接枝到橡胶相中；10-90wt％、优选40-75wt％刚性热塑性相保持“自由”即未被接枝。
橡胶改性热塑性树脂中的刚性热塑性相可以这样形成：(ⅰ)在橡胶相的存在下，通过单独聚合完成或(ⅱ)在橡胶相存在下，在完成聚合的刚性热塑性聚合物中加入一种或多种独立聚合的刚性热塑性聚合物。
在一种优选的实施方案中，在橡胶相存在下，向已经聚合的刚性热塑性聚合物中外加一种或多种独立聚合的刚性热塑性聚合物以助于调节本发明中组合物的粘度达到理想范围。在进一步高度优选的实施方案中，一种或多种分别聚合得到的刚性热塑性聚合物的重均分子量范围约为50，000-100，000g/mol。
在一种优选的实施方案中，橡胶改性热塑性树脂包括橡胶相和刚性热塑性相，其中橡胶相包括一种结构单元来自一种或多种共轭二烯单体的聚合物，还任选包括选自乙烯基芳香单体和单烯类不饱和腈单体的一种或多种单体衍生的结构单元，该刚性热塑性相包括一种含有选自乙烯基芳香单体和单烯类不饱和腈单体的一种或多种单体衍生的结构单元的聚合物。
在一种高度优选的实施方案中，橡胶改性接枝共聚物的橡胶相包括聚丁二烯或聚(苯乙烯-丁二烯)橡胶，刚性相包括苯乙烯-丙烯腈共聚物。
橡胶改性热塑性树脂中的橡胶相中每一种聚合物和刚性热塑性树脂相中的每一种聚合物任选包括，以Tg范围满足要求为条件，来自于一种或多种其他可共聚的单烯类不饱和单体的结构单元，其中单烯类不饱和羧酸如丙烯酸、甲基丙烯酸、亚甲基丁二酸；(甲基)丙烯酸羟基(C1-C12)烷基酯单体，如甲基丙烯酸羟基乙基酯；〔甲基〕丙烯酸(C4-C12)环烷基酯单体，如甲基丙烯酸环己基酯；甲基丙烯酰胺单体，如丙烯酰胺、甲基丙烯酰胺；马来酰亚胺单体，如N-烷基马来酰亚胺、N-芳基马来酰亚胺、马来酸酐；乙烯基酯类如，醋酸乙烯酯和丙酸乙烯酯。这里使用的术语“(C4-C12)环烷基”指的是每一基团上含有4-12个碳原子的环烷基取代基，术语“(甲基)丙烯酰胺”统指丙烯酰胺和甲基丙烯酰胺。
在一种优选的实施方案中，橡胶改性热塑性树脂的橡胶相粒子大小范围0.1-3.0微米(μm)，进一步优选0.2-2.0μm。
在一种优选的实施方案中，本发明中的组合物包括一种含氟聚合物，在每100pbw热塑性树脂组合物中，其数量通常为0.01-0.5pwb，可为树脂组合物提供有效的防滴漏性能。合适的含氟聚合物及其制备方法是众所周知的，参见美国专利No.3,671,487、3,723,373和3,383,092。合适的含氟聚合物包括均聚物和共聚物，其包含的结构单元来自一种或多种氟代α-烯烃单体。术语“氟代α-烯烃单体”指一种，包括至少一个氟原子取代基的α-烯烃单体合适的氟代α-烯烃单体包括如氟代乙烯，如CF2=CF2、CHF=CF2、CH2=CF2、CH2=CHF、CClF=CF2、CCl2=CF2、CClF=CClF、CHF=CCl2、CH2=CClF、CCl2=CClF和氟代丙烯如，CF3CF=CF2、CF3CF=CHF、CF3CH=CF2、CF3CH=CH2、CF3CF=CHF、CHF2CH=CHF和CF3CH=CH2。在一种优选的实施方案中，氟代α-烯烃单体是一种或多种四氟乙烯(CF2=CF2)、氯代三氟乙烯(CClF=CF2)、1，1二氟乙烯(CH2=CF2)和六氟丙烯(CF2=CFCF3)。
合适的氟代α-烯烃均聚物包括，例如聚(四氟乙烯)、聚(六氟丙烯)。
合适的氟代α-烯烃共聚物包括其结构单元来自两种或多种氟代α-烯烃的共聚物，如聚(四氟乙烯-六氟丙烯)，和包括结构单元来自于一种或多种氟代单体的共聚物，和一种或多种与氟代单体共聚的非氯代单烯类不饱和单体的共聚物，如(四氟乙烯-乙烯-丙烯)共聚物。合适的非氟代单烯类不饱和单体包括，例如α-烯烃单体如乙烯、丙烯、丁烯；丙烯酸酯单体如甲基丙烯酸甲酯、丙烯酸丁酯；乙烯基醚例如环己基乙烯基醚、乙基乙烯基醚、正丁基乙烯基醚；乙烯基酯例如醋酸乙烯酯、一种有支链的烷烃羧酸乙烯酯。
在一种优选的实施方案中，含氟聚合物粒子大小范围50-500mm，由电子显微镜测定。
在一种高度优选的实施方案中，含氟聚合物是一种聚(四氟乙烯)均聚物(“PTFE”)。
因为将含氟聚合物直接掺入热塑性树脂组合物中很困难，优选将含氟聚合物以某种方式与第二类聚合物预先共混，例如，与一种芳香族聚碳酸酯树脂或苯乙烯-丙烯腈树脂共混。例如，含氟聚合物的水分散体和聚碳酸酯树脂可由蒸汽沉淀形成一种含氟聚合物浓缩物，用作热塑性树脂组合物的阻滴剂添加剂，例如已经在美国专利No.5,521,230中公开，或者另外选择一种含水苯乙烯-丙烯腈树脂乳液或一种含水丙烯腈-丁二烯-苯乙烯树脂乳液，然后沉淀、干燥、该共凝含氟聚合物-热塑性树脂组合物，得到PTFE-热塑性树脂粉末，例如已经在美国专利No.4,579,906中公开。
在一种优选的实施方案中，含氟聚合物添加剂包括30-70wt％，进一步优选40-60wt％的含氟聚合物和30-70wt％，进一步优选40-60wt％的第二类聚合物。
在一种优选的实施方案中，一种含氟聚合物添加剂是在本发明中水相含氟聚合物分散体存在下通过一种或多种单烯类不饱和单体乳液聚合、并在含氟聚合物中形成第二类聚合物制备的。合适的单烯类不饱和单体上面已描述过，乳液例如通过添加硫酸而沉淀。沉淀物如通过离心法脱水，然后干燥形成包括含氟聚合物和一种相关第二类聚合物的含氟聚合物添加剂，干燥的乳液聚合含氟聚合物添加剂以自由流动粉末的形式存在。
在一种优选的实施方案中，可通过乳液聚合形成第二类聚合物的单烯类不饱和单体，包含选自乙烯基芳香单体、单烯类不饱和腈单体和(C1-C12)(甲基)丙烯酸(烷基)酯单体的一种或多种单体，合适的乙烯基芳香单体、单烯类不饱和腈单体和(甲基)丙烯酸(C1-C12)烷基酯单体已在上面公开。
在一种高度优选的实施方案中，第二类聚合物包括由苯乙烯和丙烯腈衍生的结构单元，进一步优选，第二类聚合物包括60-90wt％来自于苯乙烯的结构单元和10-40wt％来自于丙烯腈的结构单元。
乳液聚合反应混合物任选包括乳化的或分散的第三类聚合物粒子，例如一种乳化丁二烯橡胶胶乳。
乳液聚合反应采用一种传统自由基引发剂引发，如上面提到的关于橡胶改性接枝共聚物。
链转移剂，例如(C9-C13)烷基硫醇化合物如壬基硫醇、叔十二烷基硫醇，在聚合反应过程中任选加入到反应容器中，以减少第二类聚合物分子量。在一种优选的实施方案中，不使用链转移剂。
在一种优选的实施方案中，稳定的含氟聚合物分散相加入到反应容器中加热搅拌。接着使引发剂体系和一种或多种单烯类不饱和单体加入反应器并加热，在含氟聚合物粒子分散相中使单体聚合形成第二类聚合物。
合适的含氟聚合物添加剂和乳液聚合方法已在欧洲专利0739，941A1中公开。
在一种优选的实施方案中，第二类聚合物的重均分子量范围约为10，000-200，000g/mol。
适于用作本发明中有机磷阻燃剂是的有机磷化合物是已知的化合物，包括一元磷酸酯，例如磷酸三苯酯、磷酸三甲苯酯、磷酸三硝基甲苯酯、三苯基磷酸二苯酯、磷酸苯基双十二烷基酯、磷酸乙基二苯基酯；也可以是二磷酸酯和齐聚磷酸酯，例如二磷酸间苯二酚酯、磷酸氢二苯基酯、磷酸氢2-乙基己基酯。合适的齐聚磷酸酯化合物已在转让给Johannes C.Gossens等的美国专利No.5，672，645中提出来，“含苯乙烯共聚物和/或接枝共聚物和阻燃剂的具有芳香族聚碳酸酯的聚合物混合物及其制品”，其中内容在这里引作参考。
在一种优选的实施方案中，本发明中有机磷阻燃剂包括一种或多种结构式为(Ⅵ)的化合物：式中R1、R2、R3和R4是互相独立的芳基、任选被卤素或烷基取代，
X是亚芳基，任选被卤素或烷基取代，
a、b、c和d彼此独立地为0或1，和
n是0-5的整数，进一步优选1-5。
这里所使用的芳基指的是每个基团中含有一个或多个芳基环的单价基团，其中基团可以含有两个或多个环，也可以是稠环，及可以用一个或多个烷基选择性取代一个或多个芳香环，每一种优选(C1-C6)烷基。
这里所使用的亚芳基指的是含有一个或多个芳环的二价基团，该二价基团任选用一个或多个烷基取代一个或多个芳环，每一个烷基优选(C1-C6)烷基，其中的二价基团含有两个或多个环，环可以是稠环或由非芳烃键连接在一起，例如烷撑、烷叉，任一种均可在芳环的一个或多个位置上被卤素基团或(C1-C6)烷基取代。
在一种高度优选的实施方案中，R1、R2、R3和R4均为苯基、a、b、c和d均为1，X是亚苯基，进一步优选1，3-亚苯基：
在一种替代的高度优选的实施方案中，R1、R2、R3和R4均为苯基，a，b，c和d均为1，X是结构式为(Ⅶ)的二价基团：
在优选实施方案中，有机磷阻燃剂包括一种有机磷齐聚物的共混物，每一物质结构式为(Ⅶ)，其中每一个齐聚物中，n独立地是1-5中的整数，齐聚物共混物中n平均值为大于1、小于5，进一步优选大于1、小于3，更进一步优选大于1、小于2，还进一步优选1.2-1.7。
本发明中的热塑性树脂组合物任选含有各种传统添加剂，例如抗氧剂，如有机亚磷酸酯中的亚磷酸三(壬基-苯基)酯、亚磷酸(2，4，6-三-叔丁基苯基)(2-丁基-2-乙基-1，3-丙二醇)酯、二亚磷酸双(2，4-二-叔丁基苯基)季戊四醇酯或二亚磷酸二硬脂基季戊四醇酯，也可以是烷基化的一元酚、多元酚；多元酚与二烯的烷基化反应产物，如对甲酚和二聚环戊二烯的丁基化反应产物；烷基化氢醌、羟基化硫代二苯基醚、烷叉双酚A、苄基化合物、酰氨基苯酚、β-(3，5-二-叔丁基-4-羟基酚-丙酸与一元醇或多元醇反应而成的酯、β-(5-叔丁基-4-羟基-3-甲基苯基)丙酸与一元醇或多元醇反应而成的酯、β-(5-叔丁基-4-羟基-3-甲基苯基)丙酸与一元醇或多元醇反应而成的酯、硫代烷基、或硫代芳基化合物酯，例如，硫代丙酸二硬脂基酯、硫代丙酸二月桂基酯、硫代二丙酸双十三烷基酯、β-(3，5-二-叔丁基-4-羟基苯酚)丙酸的酰胺类；紫外线吸收剂和光稳定剂如，(ⅰ)2-(2’羟苯基)苯并三唑、2-羟基苯酮；(ⅱ)取代的和未取代苯甲酸的酯类；(ⅲ)丙烯酸酯类；(ⅳ)镍化合物；(空间)位阻胺，例如三异丙醇胺或2，4-二氯-6-(4-吗啉基)1，3，5-三嗪与1，6-二胺聚合物的反应产物；N，N’-双(2，2，4，6-四甲基-4-哌啶基)己烷；中和剂如硬酯酸镁、氧化镁、氧化锌、硬酯酸锌、水滑石(hydrotalcite)；抗冲击改性剂；填充剂和增强剂，如硅酸盐、TiO2、玻璃纤维、碳黑、石墨、碳酸钙、滑石粉、云母；及其他添加剂，如润滑剂中的四硬脂酸季戊四醇酯、EBS蜡、硅氧烷流体；增塑剂；光学增白剂；颜料；染料；着色剂；防火剂；抗静电剂；和吹塑剂，和除了上面提到的有机磷酸盐阻燃剂和含氟聚合物外的其他阻燃剂。
本发明的热塑性树脂组合物在适合形成各种组分的共混物的条件下，通过组合和混合本发明组合物的各种组分的方法制备，例如使用双辊混炼机、Banbury密炼机或单螺杆或双螺杆挤出机进行熔融混合，接着任选地，例如通过对组合物进行切粒或研磨使组合物形成颗粒。
本发明中的热塑性树脂组合物通过多种方法如注塑、挤出、旋塑、吹塑和热成型法，被模塑成有用形状的制品，例如计算机和商务机器外壳、家用电器等。
实施例1-6和比较例C1-C6
实施例1-6和比较例C1-C6使用两种不同类型ABS树脂制备。
方法A
橡胶相是由水(159pwb)中的丁二烯单体(100pwb)、在皂类(牛脂脂肪酸，3pwb)、聚合反应引发剂(过硫酸钾，0.135pwb)和链转移剂(叔十二烷基硫醇，0.2pwb)存在下经乳液聚合制备，反应混合物被均化后得到含有平均粒子大小约295nm的橡胶胶乳。一种包含大约75wt％苯乙烯和25wt％丙烯腈的刚性相随后被接枝到橡胶胶乳粒子上。
方法B
橡胶相是由水(159pwb)中的丁二烯单体(100pwb)，在皂类(Empol1018，Henkel公司，3pwb)、聚合反应引发剂(过硫酸钾，0.135pwb)、链转移剂(叔十二烷硫醇，0.55pwb)和甲醛化次硫酸钠(0.05pwb)存在下经乳液聚合制备。反应混合物被均化后得到含有平均粒子大小约310nm的橡胶胶乳。大约含75wt％苯乙烯和25wt％丙烯腈的刚性相随后被接枝到橡胶胶乳粒子上。
本发明的实施例1-6和比较例C1-C6中的热塑性树脂组合物均通过下述表Ⅰ和表Ⅱ提供的相对量(每一个均以重量分数表示)的组分组合物制备的，热塑性树脂组合物中所用组分如下：
PC-1：由双酚A和光气得到的线性聚碳酸酯树脂
PC-2：由双酚A和光气得到的线性聚碳酸酯树脂
PC-3：由双酚A和光气得到的线性聚碳酸酯树脂，且在25℃下，在二氯甲烷中其特性粘度约为47ml/g
PC-4：由双酚A和光气得到的线性聚碳酸酯树脂，且在25℃下，在二氯甲烷中其特性粘度约为49.3ml/g
PC-5：由双酚A和光气得到的线性聚碳酸酯树脂，且在25℃下，在二氯甲烷中其特性粘度约为51.7ml/g
PC-6：由双酚A和光气得到的线性聚碳酸酯树脂，且在25℃下，在二氯甲烷中其特性粘度约为54ml/g
ABS-1：由前面描述的方法A制备的丙烯腈-丁二烯-苯乙烯接枝共聚物，包含大约50wt％的溶胀指数约12.99的非连续聚丁二烯橡胶相，和约50wt％刚性苯乙烯-丙烯腈热塑性相(75wt％苯乙烯和25wt％丙烯腈共聚物)
ABS-2：由前面描述的方法B制备的丙烯腈-丁二烯-苯乙烯接枝共聚物，包含大约50wt％的溶胀指数约73.2的非连续聚丁二烯橡胶相，和约50wt％刚性苯乙烯-丙烯腈热塑性相(75wt％苯乙烯和25wt％丙烯腈共聚物)
SAN-1：75wt％苯乙烯和25wt％丙烯腈的共聚物，重均分子量约为60000g/mol；
SAN-2：75wt％苯乙烯和25wt％丙烯腈的共聚物，重均分子量约为94000g/mol；
TSAN：在PTFE水相分散体存在下，苯乙烯和丙烯腈共聚制备的添加剂(50pwbPTFE，50pbw含75wt％苯乙烯和25wt％丙烯腈的一种苯乙烯-丙烯腈共聚物)；和
RDP：二磷酸间苯二酚酯(FyroflexTMRDP，AKzo Chemicals)。
熔体粘度(“MV”)是在500°F，剪切速度500s-1、1000s-1和1500s-1下，用毛细管流变仪(Kayeness，Model8052)测定；Izod缺口冲击强度根据ASTM D256对实施例1-2和比较例C1-C2中的每一种组合物进行测定。熔体粘度用泊表示；Izod缺口冲击强度用ft-lb/in表示。每一种组合物的熔体粘度和Izod缺口冲击强度见下表Ⅰ中。
组合物被用于注塑成样条，样条外观性能由5位操作员分别评价每一种聚合物的5根样条等级范围，用1-5表示，1表示最好，5表示最差。每种组合物的5根样条的值的加和即是该组合物的总测量值，见下面表Ⅰ。表Ⅰ
熔体流动指数(MFI)用每十分钟多少克表示(“g/10min”)，Izod缺口冲击强度在23℃下，用每英寸多少英尺？磅表示(ft-1b/in)，每一种组合物的上述性能列于表Ⅱ中。
每种组合物模塑成样条用以评价边缘裂纹程度，结果如下表Ⅱ所示。表Ⅱ
Claims (13)
1、一种热塑性树脂组合物，包括：
(a)一种芳香碳酸酯树脂，
(b)一种包括分散在连续刚性热塑性相中的非连续橡胶相的橡胶改性接枝共聚物，其中至少一部分刚性热塑性相被化学接枝到橡胶相中，其中共聚物中橡胶相是在(C30-C108)多元酸表面活性剂存在下，通过水相乳液聚合制备，和
(c)一定阻燃量的有机磷阻燃剂。
2、权利要求1中的组合物，其中该组合物包括，以100重量份热塑性树脂组合物计的，40-95重量份的芳香族聚碳酸酯树脂，4-59重量份的橡胶改性接枝共聚物和1-20重量份的有机磷酸酯阻燃剂。
3、权利要求1中的组合物，其中聚碳酸酯树脂是由双酚A和光气衍生来的。
4、权利要求1中的组合物，其中橡胶相包括一种聚丁二烯聚合物或聚(苯乙烯-丁二烯)共聚物和刚性热塑性相，其包括选自乙烯基芳香单体和单烯类不饱和腈单体的一种或多种单体衍生的结构单元。
5、权利要求4中的组合物，其中刚性相包括一种由选自苯乙烯、α-甲基苯乙烯和丙烯腈的单体衍生的共聚物。
9、权利要求8中的组合物，其中乳液聚合是在一定量的链转移剂存在的条件下完成的，链转移剂的量有效地提供溶胀指数大于15的橡胶；
10、权利要求1中的组合物，其中有机磷阻燃剂包括一种或多种结构式为(Ⅵ)的化合物，其中R1、R2、R3和R4是相互独立的芳基，该芳基可以被卤素、烷基选择性取代，
X是亚芳基，任选被卤素、烷基取代，
a、b、c和d彼此独立地为0或1，和
n是0-5中的一个整数。
11、权利要求1中的组合物，其中该组合物进一步包括一种含氟聚合物，以一定的量有效地提供组合物以防滴漏性能；
12、权利要求1中的组合物，其中该含氟聚合物是一种四氟乙烯聚合物。
13、权利要求1中的组合物，其中该含氟聚合物以一种添加剂的形式加到组合物中，该添加剂是在含氟聚合物的水分散体存在下，由一种或多种单烯类不饱和单体经乳液聚合制备。
14、权利要求13中的组合物，其中该添加剂是在聚四氟乙烯颗粒的水分散体存在下，由苯乙烯和丙烯腈经乳液聚合制备。
15、一种由权利要求1中的组合物模塑而成的制品。
16、一种热塑性树脂组合物，包括由如下组分共混而成的组合物：
(a)一种聚碳酸酯树脂，
(b)一种橡胶改性接枝共聚物，包括分散在一种连续刚性热塑性相中的非连续橡胶相，其中至少一部分刚性热塑性相被化学接枝到橡胶相上，所说的橡胶改性接枝共聚物是在(C30-C108)多元酸表面活性剂存在下由水相乳液聚合制备，和
(c)一定阻燃量的有机磷阻燃剂。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/050,779 US6084054A (en) | 1998-03-30 | 1998-03-30 | Flame retardant polycarbonate resin/ABS graft copolymer blends having low melt viscosity |
| US09/050,779 | 1998-03-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1295599A true CN1295599A (zh) | 2001-05-16 |
| CN1235974C CN1235974C (zh) | 2006-01-11 |
Family
ID=21967378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB998047074A Expired - Fee Related CN1235974C (zh) | 1998-03-30 | 1999-02-05 | 阻燃聚碳酸酯树脂/abs接枝共聚物的共混物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6084054A (zh) |
| EP (1) | EP1080153B1 (zh) |
| JP (1) | JP4180796B2 (zh) |
| KR (2) | KR100800898B1 (zh) |
| CN (1) | CN1235974C (zh) |
| DE (1) | DE69943373D1 (zh) |
| MY (1) | MY116321A (zh) |
| TW (1) | TW570956B (zh) |
| WO (1) | WO1999050353A1 (zh) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6605659B2 (en) | 2000-12-20 | 2003-08-12 | General Electric Company | Flame retardant polycarbonate resin/ABS graft copolymer blends |
| EP1349893B1 (en) * | 2000-12-20 | 2007-04-18 | General Electric Company | Flame retardant polycarbonate resin/abs graft copolymer blends |
| JP4903998B2 (ja) | 2002-10-15 | 2012-03-28 | エルジー エレクトロニクス インコーポレイティド | 記録された複数のグラフィックストリームの再生を管理するためのデータ構造を有する記録媒体、それによる記録及び再生方法及び装置 |
| CN101096449B (zh) * | 2006-06-30 | 2010-05-26 | 佛山市顺德区汉达精密电子科技有限公司 | 一种pc/abs合金材料 |
| CN101139459B (zh) * | 2007-08-30 | 2011-12-21 | 上海金发科技发展有限公司 | 一种无卤阻燃耐热聚碳酸酯和丙烯腈-丁二烯-苯乙烯接枝共聚物合金树脂及其制备方法 |
| CN101671470B (zh) * | 2009-10-13 | 2011-03-16 | 青岛国恩科技发展有限公司 | 一种阻燃高韧性复合材料及制造方法 |
| US10190051B2 (en) | 2014-06-10 | 2019-01-29 | Alexium, Inc. | Emulsification of hydrophobic organophosphorous compounds |
| CN105713326B (zh) * | 2016-03-07 | 2017-09-01 | 江西江铃李尔内饰系统有限公司 | 一种汽车座椅 |
| KR102044364B1 (ko) * | 2016-11-11 | 2019-11-13 | 주식회사 엘지화학 | 열가소성 수지 및 열가소성 수지 조성물 |
| EP3632938B1 (en) * | 2018-10-05 | 2023-05-03 | Trinseo Europe GmbH | Vinylidene substituted aromatic monomer and cyclic (meth)acrylate ester polymers |
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| US2664429A (en) * | 1949-08-15 | 1953-12-29 | Emery Industries Inc | Method for manufacturing polymerized fatty acids |
| NL93409C (zh) * | 1954-12-13 | |||
| NL92418C (zh) * | 1954-12-13 | |||
| BE570531A (zh) * | 1957-08-22 | |||
| NL255206A (zh) * | 1959-08-24 | |||
| US3076003A (en) * | 1960-09-22 | 1963-01-29 | Emery Industries Inc | Process for polymerizing unsaturated fatty acids |
| US3544514A (en) * | 1965-01-15 | 1970-12-01 | Bayer Ag | Process for the production of thermoplastic polycarbonates |
| US3635895A (en) * | 1965-09-01 | 1972-01-18 | Gen Electric | Process for preparing thermoplastic polycarbonates |
| DE1568782A1 (de) * | 1966-08-24 | 1970-03-26 | Henkel & Cie Gmbh | Verfahren zur kontinuierlichen Dimerisierung von Estern ungesaettigter Fettsaeuren |
| US3671487A (en) * | 1971-05-05 | 1972-06-20 | Gen Electric | Glass reinforced polyester resins containing polytetrafluoroethylene and flame retardant additives |
| US3723373A (en) * | 1971-10-04 | 1973-03-27 | American Cyanamid Co | 0.1% to about 2.0% by weight polytetrafluoroethylene emulsion modified polyethylene terephthalate with improved processing characteristics |
| US3925342A (en) * | 1973-10-15 | 1975-12-09 | Arizona Chem | Polymerization of unsaturated fatty materials |
| US4001184A (en) * | 1975-03-31 | 1977-01-04 | General Electric Company | Process for preparing a branched polycarbonate |
| US4430484A (en) * | 1981-01-14 | 1984-02-07 | General Electric Company | Polyester-carbonate resin blends |
| US4487896A (en) * | 1983-09-02 | 1984-12-11 | General Electric Company | Copolyester-carbonate compositions exhibiting improved processability |
| DE3403975A1 (de) * | 1984-02-04 | 1985-08-14 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von abs-formmassen mit verbessertem brandverhalten |
| US5204394A (en) * | 1988-09-22 | 1993-04-20 | General Electric Company | Polymer mixture having aromatic polycarbonate, styrene I containing copolymer and/or graft polymer and a flame-retardant, articles formed therefrom |
| CA2058343C (en) * | 1991-01-07 | 2002-08-13 | Charles E. Lundy | Pigmented polycarbonate composition having high impact strength and good cosmetics |
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| US5521230A (en) * | 1992-11-17 | 1996-05-28 | General Electric Company | Method of dispersing solid additives in polymers and products made therewith |
| DE4328656A1 (de) * | 1993-08-26 | 1995-03-02 | Bayer Ag | Flammwidrige, spannungsrißbeständige Polycarbonat-ABS-Formmassen |
| US5354791A (en) * | 1993-10-19 | 1994-10-11 | General Electric Company | Epoxy-functional polyester, polycarbonate with metal phosphate |
| EP0714949A2 (en) * | 1994-12-02 | 1996-06-05 | General Electric Company | Processes, thermoplastic compositions and emulsion graft copolymer utilizing a polyacid |
| FR2733504A1 (fr) * | 1995-04-28 | 1996-10-31 | Gen Elec Plastics Abs Euro Bv | Nouveaux alliages polymeres a base de polymerisat comprenant des motifs de derives de tetrafluoroethylene, procede de fabrication, articles obtenus a partir de tels alliages et utilisation de ces alliages dans des compositions polymeres |
| JPH08319406A (ja) * | 1995-05-26 | 1996-12-03 | Kanegafuchi Chem Ind Co Ltd | 難燃性樹脂組成物 |
| TW386099B (en) * | 1995-07-26 | 2000-04-01 | Gen Electric | Flame resistant compositions of polycarbonate and monovinylidene aromatic compounds |
| SG72704A1 (en) * | 1995-11-01 | 2000-05-23 | Gen Electric | Flame retardant thermoplastic composition containing aromatic polycarbonate resins and a rubber modified graft copolymer |
| US6040370A (en) * | 1997-04-17 | 2000-03-21 | General Electric Company | Aqueous fluoropolymer dispersion and method for making fluoropolymer-containing thermoplastic resin composition |
-
1998
- 1998-03-30 US US09/050,779 patent/US6084054A/en not_active Expired - Lifetime
-
1999
- 1999-02-05 KR KR1020067022296A patent/KR100800898B1/ko not_active IP Right Cessation
- 1999-02-05 CN CNB998047074A patent/CN1235974C/zh not_active Expired - Fee Related
- 1999-02-05 DE DE69943373T patent/DE69943373D1/de not_active Expired - Lifetime
- 1999-02-05 KR KR1020007010887A patent/KR20010042333A/ko not_active Application Discontinuation
- 1999-02-05 WO PCT/US1999/002585 patent/WO1999050353A1/en not_active Application Discontinuation
- 1999-02-05 JP JP2000541248A patent/JP4180796B2/ja not_active Expired - Fee Related
- 1999-02-05 EP EP99906773A patent/EP1080153B1/en not_active Expired - Lifetime
- 1999-03-27 MY MYPI99001196A patent/MY116321A/en unknown
- 1999-03-29 TW TW088104957A patent/TW570956B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US6084054A (en) | 2000-07-04 |
| JP2002509972A (ja) | 2002-04-02 |
| WO1999050353A1 (en) | 1999-10-07 |
| CN1235974C (zh) | 2006-01-11 |
| TW570956B (en) | 2004-01-11 |
| DE69943373D1 (de) | 2011-06-01 |
| KR20060126840A (ko) | 2006-12-08 |
| EP1080153B1 (en) | 2011-04-20 |
| EP1080153A1 (en) | 2001-03-07 |
| KR20010042333A (ko) | 2001-05-25 |
| JP4180796B2 (ja) | 2008-11-12 |
| MY116321A (en) | 2003-12-31 |
| KR100800898B1 (ko) | 2008-02-04 |
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