CN1090560C - 塑料基多层结构和具有多层结构的管 - Google Patents
塑料基多层结构和具有多层结构的管 Download PDFInfo
- Publication number
- CN1090560C CN1090560C CN97181379A CN97181379A CN1090560C CN 1090560 C CN1090560 C CN 1090560C CN 97181379 A CN97181379 A CN 97181379A CN 97181379 A CN97181379 A CN 97181379A CN 1090560 C CN1090560 C CN 1090560C
- Authority
- CN
- China
- Prior art keywords
- layer
- polyamide
- polyvinylidene fluoride
- composition
- acid ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
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- Y10T428/31725—Of polyamide
- Y10T428/31739—Nylon type
- Y10T428/31743—Next to addition polymer from unsaturated monomer[s]
Abstract
本发明涉及一种塑料基多层结构,特别用于制备传输液态流体如醇、来自石油的液体燃料、含有氧化合物如醇的燃料所用管材或导管的多层结构。更特别地本发明涉及特别对于上述流体具有改进阻挡性能的多层结构。该结构包含由聚酰胺基组合物形成的外层(A)和由聚偏氟乙烯基组合物形成的内部邻接层(B)。这两层间的粘附或是由在形成层(B)的聚合物中加入注册商标为RESEDA的市售聚丙烯酸酯化合物、或是由含有该RESEDA化合物的组合物形成处在邻接层(A)和(B)之间的中间层而获得。
Description
本发明涉及一种塑料基多层结构,尤其是适合于制造传输液态流体如醇类、来自石油的液体燃料、可能含有氧化合物如醇类的燃料所用管材或导管的多层结构。
本发明尤其涉及一种特别对于上述流体具有改进的阻挡性能的多层结构。
塑料管材和导管用于在内燃机中传输流体如燃料属于公知内容。例如,聚酰胺-12管材或导管通常被用于汽车。
然而,与机动车结构有关的规范、特别是力图防治由机动车产生的大气污染的规范变得越来越严格。
因此,具有单层结构的导管和管材例如由聚酰胺-12制得的那些,不能满足加在内燃机上的新的技术要求。因此,在满足涉及阻挡燃料蒸气性能的规范和特性的同时仍保持合适的机械性能如挠性、抗龟裂性和尺寸稳定性变得非常困难。
为了克服这些缺点,已经有人提出具有多层结构的管材或导管,其中包括聚酰胺(特别是聚酰胺-11或聚酰胺-12)层和乙烯基醚醇层(参见法国专利2,579,290、EP 0,428,834和EP 0,428,833)。然而,这些管材的使用已经说明它们无法满足用于内燃机中的所有必要特性。
人们也曾推荐包含作为外层的聚酰胺-11和作为内层的聚偏氟乙烯的多层结构。聚偏氟乙烯特别用苯磺酰胺增塑。然而,由于上述情况,这样的结构不能满足它们的主要应用如内燃机的燃料管所要求的特性。特别地,这样的结构的层间粘合力不足。
人们也曾推荐包含粘结在聚酰胺层上的聚偏氟乙烯层的多层结构。为了提高这些层间的粘合力并因而提高整个多层结构的性能,推荐使用一种聚偏氟乙烯组合物,该组合物包含或是戊二酰亚胺聚合物(EP 0,637,511)或是一种丙烯酸酯共聚物,其中该共聚物至少包含由两个相邻羧酸官能团的环化作用得到的酐官能团。EP 0618390提出在聚酰胺层与PVDF层之间设置丙烯酸聚合物层。然而,该结构的各层间的粘合力和该结构的机械性能在老化过程中会变差。
本发明的目的之一是提供一种多层结构,该结构具有改进的机械和阻挡性能,并具有一组适合于生产或制备传输流体、特别是燃料、更特别是含有含氧化合物如醇的燃料所用导管或管材的性能。
为此目的,本发明提供一种多层结构,该结构包含至少一个由聚酰胺基组合物形成的层(A)和至少一个由聚偏氟乙烯基组合物形成的邻接层(B)。根据本发明,由于在层(A)和层(B)中至少一层中存在包含下式(i)和(ii)重复单元和视具体情况而存在的式(iii)和/或(iv)重复单元的聚丙烯酸酯化合物增进两层间的粘合力:其中:R,R1:相同或不同地表示氢或含有1~12个碳原子的烷基,R2: 是式R4-T基团,其中R4是烷基、芳基、芳烷基或烷芳基,
本发明还涉及一种多层结构,该结构包含如上所述的至少一个由聚酰胺基组合物形成的层(A)和至少一个由聚偏氟乙烯基组合物形成的邻接层(B)。然而,在本发明的该实施方案中,该结构包含粘附中间层(C),其位于层(A)和(B)之间并由包含至少一种上述聚丙烯酸酯化合物的组合物形成。在该实施方案中,分别形成层(A)和(B)的聚酰胺和聚偏氟乙烯组合物可能包含或不包含上述聚丙烯酸酯化合物。
在说明书的其余部分,“一种或该聚丙烯酸酯化合物”指的是如上所述化合物,除非另有说明。
按照本发明的优选实施方案,当不存在中间层(C)时,聚丙烯酸酯化合物存在于形成层(B)的聚偏氟乙烯组合物中。
按照本发明的另一优选实施方案,多层结构包含不含有聚丙烯酸酯化合物的聚偏氟乙烯层。该层可以是上述的层(B),其结构包含或是层(C)(层(C)粘接于包含或不包含聚丙烯酸酯化合物的层(A)上),或是包含丙烯酸酯化合物的层(A)。没有聚丙烯酸酯化合物的聚偏氟乙烯层也可以作为添加层存在,该层粘接于具有本发明结构的层(B)上。
由于被有利地放于内侧或下侧的聚偏氟乙烯层的存在,即该层最接近于由该多层结构所制装置中含有的液体,本发明的多层结构特别对于存在于燃料中的含氧化合物如醇显示出非常好的阻挡性能。该聚偏氟乙烯层是本发明的层(B)。
由于作为外层的具有良好抗应力开裂性的聚酰胺层的存在,本发明的结构也显示出非常好的机械性能。作为有用的机械性能的例子,特别是在低温下,可以提及的是抗龟裂性和抗冲击性。
因此,适合于本发明的聚酰胺特别是脂族聚酰胺和共聚酰胺,如PA 4,6;PA 6,6;PA 6,12;PA 6,10;PA 6;PA 11和PA 12。
由于共聚酰胺特别适合于本发明,可以提及的是PA 6/6,36共聚酰胺和PA 6与PA 6/6,36的合金。
在美国专利U.S.5,256,460和未公开的法国申请95/11681中特别描述了这些共聚酰胺或聚酰胺合金。
根据本发明的优选特征,聚酰胺组合物包含一种增塑剂如磺酰胺化合物、一种聚亚烷基二醇如聚乙二醇或一种对羟基苯甲酸的烷基酯。
聚酰胺组合物也可包含增加韧性的试剂如弹性体、通用添加剂如热或光稳定剂、用于提高组合物加工性能(注塑或挤出)的添加剂、用于提高如抗静电性能的填料、颜料或类似物质。
在著作“Kunststoff-Handbuch[塑料手册],第一版,第XI卷,pp.403以及后续内容,由Carl Hanser Verlag,Munich(1971)出版或Hans R.Kricheldorf在“Handbook of Polymer Synthesis”的Ar部分,pp.191以及后续内容,由Marcel Dekker Inc.出版中特别描述了适合于本发明的聚偏氟乙烯的结构和制备方法。
聚偏氟乙烯可以是偏氟乙烯与其它单体如三氟乙烯、乙烯、六氟丙烯、氯三氟乙烯的共聚物,或聚偏氟乙烯混合物。
该组合物也可包含所有常见和通用的添加剂,如加工助剂、热和光稳定剂、颜料、填料或类似物质。
根据本发明,聚丙烯酸酯化合物包含有利地连接于聚丙烯酸结构的羧酸基团上的酸、胺、酐或环氧官能团。更一般地,适合于本发明的聚丙烯酸酯化合物含有与聚酰胺的胺或酸官能团反应的官能团。
本发明的优选官能团是与含有缩水甘油基的化合物进行成盐反应的聚丙烯酸化合物的环氧官能团、羧酸官能团。
有利地,官能团T或活性官能团、优选环氧基团的浓度相对于聚丙烯酸酯化合物为0.1meq/g~1meq/g。
本发明的优选聚丙烯酸酯化合物是具有式(i)和(ii)的甲基丙烯酸酯型重复单元的那些。
有利地,本发明的优选聚丙烯酸酯化合物是包含式(iii)重复单元的那些,其中R5表示聚甲基丙烯酸甲酯链。
作为适用于本发明的聚丙烯酸酯化合物,作为例子可以提及的是包含缩水甘油基的乙烯/丙烯酸共聚物,其在杂志《聚合物》32,Vol.1,p.19(1991)以标题“通过自由基反应制备嵌段和接枝共聚物的新方法”出版的Takashi Yamamoto文章中有述并由日本油品脂肪公司以商标“MODIPER”出售,和聚甲基丙烯酸酯,其也包含缩水甘油基官能团并由Toua Gosei公司以商标RESEDA出售。
根据本发明的一个特征,聚丙烯酸酯化合物以组合物的5~25wt%、优选10~20wt%的浓度存在于形成层A或层B的组合物中。
中间层C可以仅由聚丙烯酸酯或更有利地由聚丙烯酸酯和聚偏氟乙烯的共混物组成,有利地,聚丙烯酸酯浓度是形成该中间层的组合物的5~99wt%。
根据另一实施方案,该中间层还可包含聚酰胺,有利地,该聚酰胺与组成形成层A的组合物的聚酰胺性质相同。
相对于所有这些组分,中间层C组分的优选重量比是:
5%-100%聚丙烯酸酯化合物
0%-95%聚偏氟乙烯
0%-90%聚酰胺(当聚酰胺存在于层C中时,聚偏氟乙烯的重量浓度大于5%)。
这些浓度的总和等于100%。
与层A和B的厚度相比,形成粘附层的该中间层C具有较小的厚度。有利地,该厚度具有大约几个微米~零点几个毫米。
该中间层可以任何方式被放置于层A和B之间。
然而,在本发明的优选实施方案中,该层将与其它层A和B一起被共挤出。
通过熔融共混组合物的各种组分,按照生产其它添加剂与聚合物的共混物的常用方法制备各种组合物。
因此,有利地在高于聚丙烯酸酯和其它聚合物的熔点温度,聚丙烯酸酯化合物与聚偏氟乙烯和/或聚酰胺共混。一般在单螺杆或双螺杆挤出机中在200~320℃的温度下制备该共混物。
通过以形成制品所需的形状同时挤出或注塑各种层而获得多层结构。
因此,其壁具有本发明多层结构的制品是例如管材和导管,它们被有利地用于传输液态流体如醇、燃料、特别是含有含氧化合物如醇的燃料,更一般地是来自石油馏分的制品以及制冷剂。
这些制品也可以是中空体,用于盛装液体如上述的那些,例如内燃机的油箱。
这些制品有利地由共挤出本发明的形成器壁的各种层而获得。
本发明的多层结构可以包含可交替排列的几个层A和B。
它们也可包含作为外层或内层的层,这些层由与形成层A和B的材料不同的材料制成,例如导管或容器可以包含由乙烯醚醇制得的内层。
而且,层A结构可以具有不同的组成,这同样适用于层B。
另外,特定的层A或B,特别是外层,可以包含导电填料,以便消除静电荷。
最后,层A和B的厚度可以变化,且有利地是0.1mm~1mm。
本发明的其它目的、优点和细节将由于仅作为说明给出的下面的实施例和附图而变得更加清楚,其中:
-图1a、1b和1c是由扫描电子显微镜得到的实施例1、2和3的各自组合物的显微分析照片,和
-图2a和2b是由扫描电子显微镜得到的实施例4和9c的各自管壁横截面的显微分析照片。
在下面实施例中说明的本发明的多层结构被用于由共挤出各种层得到的管材或导管的生产。
因此,通过使用包含三个单挤出螺杆的共挤出设备得到管材,这些螺杆具有相应于各自外层、芯层和内层的L/D(长度/直径)比分别为35、30和35。
组成各种层的材料的特性和所制管材的性能按照下述方法测定。
聚酰胺的相对粘度如下测定:在25℃将它们溶解于96%的硫酸溶液中以获得由0.5wt%的聚合物构成的溶液,并按照ASTM D-789标准或ISO 307标准测试其粘度。
按照ASTM D 1238标准或ISO 1133标准在5kg负载下在230℃测定聚偏氟乙烯的熔体流动指数(MFI)。
所制管材的渗透率由静态方法测定。用涂有燃料耐性粘合剂的尼龙塞封住长度为300mm的管试样的一端。该管通过其另一端与25cm3容积的油箱相连,以便保持管中燃料的组成不变。调节管的温度和流体浸渍以直接测定渗透率。在40℃进行试验并在设定的时间段如24小时后通过重量损失测定渗出。
因此,渗透率对应于当连续时段内的重量损失不变时测定的试样的重量损失速率。
所用燃料是称为M15的标准燃料,并具有下面重量组成:
-42.5%甲苯
-42.5%异辛烷
-15%甲醇。
每层间的机械粘合力如下测定:使用金属刀片以5°切割角并沿着管材的母线切割管材,然后施加2.5kg的负载。如果层间的粘合力不足,它们将会分离。然而,当粘合力足够大时,观测不到层的分离或者分离线在层的厚度之内。
使用机头速度为250mm/min.的INSTRON 4025设备进行剥离试验。
本发明结构的层间粘合力、更特别是组成两邻接层的材料间的相容性,通过扫描电子显微分析进行测定。由此观测分散相的粒径分布和两层间界面的粘合状态。为了进行此观测,在液氮中冷却管样并将其断裂。用一薄层金将其涂敷后,使用PHILIPS 515显微镜对其进行检测。实施例1~3多层结构中某一层的制造方法
在有或没有聚丙烯酸酯化合物的情况下,制备聚酰胺/聚偏氟乙烯(PVDF)共混物,然后通过使用上述方法借助显微技术对其进行分析,以便证实丙烯酸酯化合物的相容作用。
包含20重量份PA 6/6,36聚酰胺(其相对粘度为3.2)和20重量份PVDF(其在5kg负载下在230℃时熔体流动指数(MFI)为2,并由Solvay公司以商标SOLEF 61010出售)的共混物,是在没有溶剂的情况下通过将两种聚合物熔融共混制得的。
两种其它组合物是通过向上述共混物中分别加入基于组合物总量10wt%和20wt%的聚丙烯酸酯化合物而制得的。聚丙烯酸酯化合物是含有环氧官能团T和式(iii)的聚甲基丙烯酸甲酯重复单元的聚甲基丙烯酸酯。该化合物由Toua Gosei以商标RESEDA GP-301出售。
这些共混物的一些性能在下面的表I中给出:表I
性能 | PA/PVDF(1∶1)共混物 | PA/PVDF(1∶1)共混物+10%RESEDAGP-301 | PA/PVDF(1∶1)共混物+20%RESEDAGP-301 |
断裂伸长(%) | 271 | 349 | 351 |
抗张强度(MPa) | 41 | 50 | 53 |
IZOD切口冲击强度(J/m) | 31 | 42 | 51 |
Tg(℃) | -33/65 | 59 | 59 |
显微分析 | 图1a | 图1b | 图1c |
这些结果证实聚丙烯酸酯化合物特别是在仅有一个玻璃化温度(Tg)存在下对于PA/PVDF共混物所产生的相容性影响。
该相容作用也可由基于这些组合物每一个的显微分析证实,显微分析说明了聚酰胺基质中PVDF球的消失。
实施例4
使用上述共挤出设备生产具有由两个叠加层构成的壁结构的管材。
外层由聚酰胺的组合物构成,该组合物包含1重量份相对粘度为3.8的PA 6聚酰胺和2重量份相对粘度为3.2的PA 6/6,36共聚酰胺。以每100重量份聚酰胺为基准计,该组合物还包含30重量份的锌中和的离聚物(由Exxon公司以商标IOTEK 7010出售)和8重量份的增塑剂(N-丁基苯磺酰胺)。
该外层显示出良好的抗龟裂性,特别是在CaCl2或ZnCl2溶液中的抗应力开裂性。该组合物也具有低的甲醇吸收性和对无铅燃料和非氧燃料、更特别是不含醇燃料的低渗透性。
内层由含有80wt%聚偏氟乙烯和20wt%丙烯酸酯化合物的共混物构成。聚偏氟乙烯由Solvay公司以商标SOLEF 61010出售并具有熔体流动指数(MFI)为2(在5kg负载和230℃下测试)。丙烯酸酯化合物由Toua Gosei公司以商标RESEDA GP-301出售。
外层的挤出温度是250℃,内层的挤出温度是210℃。
管材具有外径为8mm,壁厚为1mm。
外层厚度是0.85mm,内层厚度是0.15mm。
实施例9c
作为比较,用与实施例4中的管材相同的外层和用仅含有聚偏氟乙烯的组合物得到的内层,在没有增塑剂的情况下生产具有相同尺寸和结构的管材。挤出条件与实施例4相同。
每一管材壁结构的横截面的显微分析(在图2a和2b中说明),清楚地显示在实施例9c中,两层间没有粘合力(图2b)。
相反,实施例4中管材壁的层间粘合力是无间断的(图2a)。
其它特性如对燃料的渗透性和结构的粘合力在下面的表II中给出。
实施例5
用与实施例9c组成相同的外层和内层制备包含具有3个叠加共挤出层的壁结构的管材,只是具有不同厚度,且挤出条件与实施例4相同。
中心中间层或粘附层由一种共混物构成,该共混物包含1重量份的相对粘度为3.2的PA 6/6,36聚酰胺和1重量份的上述的聚偏氟乙烯。以100重量份PA/PVDF共混物计,该共混物也包含20重量份的聚丙烯酸酯化合物RESEDA GP-301。
管壁的渗透性和粘合特性在下面的表II中给出。
实施例6
制备具有由三个与实施例5相似的共挤出层的结构的管材。然而,中心中间层或粘附层由一种组合物获得,该组合物由80wt%如前面实施例中所述的PVDF和20wt%RESEDA GP-301聚丙烯酸酯相容剂的共混物构成。
该管材的性能也在下面的表II中给出。
作为比较,测定管材壁的渗透性和视具体情况而定测定其粘合性,其中管壁分别由与实施例4(实施例7c)中管材的外层对应的聚酰胺组合物单层、由与实施例5(实施例8c)中内层对应的PVDF组合物单层和由具有两个共挤出层的结构(其外层由与实施例4中的外层相同的聚酰胺组合物制得,其内层由与实施例5(实施例9c)中的内层相同的PVDF组合物制得)构成。
实施例10
制备其它实施例,其中外层是由与实施例4组成相同的聚酰胺制得,只是弹性体是由Exxon公司以商标EXXELOR 8013出售的化合物,内层是由Solvay公司以商标SOLEF 1009出售的聚偏氟乙烯均聚物。
中间层是PA 6/6,36共聚酰胺、由Solvay公司以商标SOLEF 35108出售的聚偏氟乙烯和实施例4中所用的RESEDA GP-301丙烯酸酯化合物的共混物。这些各种组分的重量含量如实施例5表示。
实施例11
用由聚酰胺(含有28%弹性体EXXELOR 8013和7%增塑剂N-丁基苯磺酰胺的PA 6)制得的外层和由PVDF,SOLEF 1009制得的内层制备与实施例5相同的管材。中间层由PVDF、PA 6和丙烯酸酯化合物的共混物制得。
PVDF是由Solvay公司以商标SOLEF 35108出售的聚偏氟乙烯共聚物。
丙烯酸酯化合物是RESEDA GP-301化合物。
这些各种管材的性能在下面的表中给出。表II
实施例 | 层的组成(th:厚度,mm) | 40℃时渗透性(g/m2.24h) | 层间粘合性 | |
4 | 外层:内层: | 聚酰胺(th:0.85)PVDF/RESEDA(th:0.15) | 80 | 良好 |
5 | 外层:芯层:内层: | 聚酰胺(th:0.85)PA/PVDF/RESEDA(th:0.1)PVDF(th:0.10) | <40 | 良好 |
6 | 外层:芯层:内层: | 聚酰胺(th:0.80)PVDF/RESEDA(th:0.1)PVDF(th:0.10) | <40 | 良好 |
7c | 聚酰胺(th:1.0) | 290 | -- | |
8c | PVDF(th:0.1) | 50 | -- | |
9c | 外层:内层: | 聚酰胺(th:0.85)PVDF(th:0.15) | 110 | 无 |
10 | 外层:芯层:内层: | 聚酰胺(th:0.8)PA/PVDF/RESEDA(th:0.1)PVDF(th:0.1) | 9 | 良好 |
11 | 外层:芯层:内层: | 聚酰胺(th:0.8)PA/PVDF/RESEDA(th:0.1)PVDF(th:0.1) | 9 | 优异 |
本发明的组合物在盐溶液中也显示出良好的抗龟裂性。(该抗龟裂性由1963年6月出版并于1990年6月12日修订的国际标准SAE.J.844中描述的ZnCl2试验测定)。
Claims (18)
2、一种多层结构,其中包含至少一个由聚酰胺基组合物形成的层(A)和至少一个由聚偏氟乙烯基组合物形成的邻接层(B),其特征在于其包含位于层(A)和(B)之间的粘附中间层(C),该层(C)由包含至少一种聚丙烯酸酯化合物的组合物形成,该聚丙烯酸酯化合物包含下式(i)和(ii)重复单元和视具体情况而存在的式(iii)和/或(iv)重复单元:其中:R,R1:相同或不同地表示含有1~12个碳原子的烷基,R2: 是式R4-T的基团,其中R4是烷基、芳基、芳烷基或烷芳基,
且T表示胺、环氧基、酸或酐官能团和/或其中:R5表示聚(甲基)丙烯酸烷基酯链R3表示含有1~6个碳原子的烷基,n:是介于1~4的整数。
3、权利要求1或2的结构,其特征在于其构成中空制品的壁。
4、权利要求1或2的结构,其特征在于聚酰胺选自于包括PA 4,6;PA 6,6;PA 6,12;PA 6,10;PA 6;PA 11;PA 12;PA 6,36;PA 6/6,36,和这些聚酰胺的混合物的脂族聚酰胺和共聚酰胺。
5、权利要求4的结构,其特征在于聚酰胺是PA6和PA6/6,36共聚酰胺的共混物。
6、权利要求1或2的结构,其特征在于式R4-F中的符号F表示环氧官能团。
7、权利要求6的结构,其特征在于R2基团是缩水甘油基。
8、权利要求1或2的结构,其特征在于聚丙烯酸酯化合物中官能团F的浓度是基于聚丙烯酸酯化合物的0.1meq/g~1meq/g。
9、权利要求1或2的结构,其特征在于聚丙烯酸酯化合物包含式(iii)的重复单元,其中R5是聚甲基丙烯酸甲酯链。
10、权利要求1或2的结构,其特征在于聚丙烯酸酯化合物以基于组合物的5wt%~25wt%的浓度存在于聚偏氟乙烯基组合物中。
11、权利要求10的结构,其特征在于聚丙烯酸酯化合物的浓度介于10~20%之间。
12、权利要求2的结构,其特征在于中间层(C)包含聚偏氟乙烯和/或聚酰胺。
13、权利要求12的结构,其特征在于中间层(C)具有下面的重量组成:
5%-100%丙烯酸酯化合物
0%-95%的聚偏氟乙烯
0%-90%的聚酰胺,且当聚酰胺存在于层C中时,聚偏氟乙烯的重量浓度大于5%,这些浓度的总和等于100%。
14、权利要求2的结构,其特征在于形成层(A)的组合物包含权利要求1的聚丙烯酸酯。
15、权利要求1或2的结构,其特征在于形成层(A)的聚酰胺组合物包含一种增塑剂。
16、权利要求1~15中之一的多层结构在制备用于盛装燃料的导管或容器方面的用途。
17、权利要求16的用途,其特征在于导管是内燃机燃料用导管。
18、权利要求1~15中之一的多层结构在通过共挤出具有该结构的层制造中空体方面的用途。
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FR96/16074 | 1996-12-20 | ||
FR9616074A FR2757444B1 (fr) | 1996-12-20 | 1996-12-20 | Structure multicouche a base de plastique et tube a structure multicouche |
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US (1) | US6964800B2 (zh) |
EP (1) | EP0946362B1 (zh) |
JP (1) | JP3367679B2 (zh) |
CN (1) | CN1090560C (zh) |
AT (1) | ATE227643T1 (zh) |
AU (1) | AU5855298A (zh) |
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CA (1) | CA2275349C (zh) |
DE (1) | DE69717142T2 (zh) |
DK (1) | DK0946362T3 (zh) |
ES (1) | ES2182151T3 (zh) |
FR (1) | FR2757444B1 (zh) |
PL (1) | PL334098A1 (zh) |
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US6432542B1 (en) | 1997-11-06 | 2002-08-13 | Alliedsignal Inc. | Multicomponent structures having improved adhesion |
EP1362890B2 (de) * | 2002-05-07 | 2016-09-28 | Ems-Chemie Ag | Gewellter Mehrschicht-Polymer-Schlauch- oder Rohrleitung mit reduzierter Längenänderung |
FR2840848B1 (fr) * | 2002-06-13 | 2004-10-15 | Inst Francais Du Petrole | Structure multicouche a permeabilite controlee |
DE102004048776A1 (de) * | 2004-10-07 | 2006-04-13 | Degussa Ag | Mehrschichtverbund mit EVOH-Schicht und Schutzschicht |
WO2008011002A1 (en) * | 2006-07-21 | 2008-01-24 | Continental Automotive Systems Us, Inc. | Auxiliary side hose connection for dual chamber fuel tank |
KR20100112139A (ko) * | 2007-12-21 | 2010-10-18 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 플루오로중합체 다중층 물품 |
ES2685770T3 (es) | 2008-10-03 | 2018-10-11 | Uponor Innovation Ab | Métodos y composiciones para recubrimiento de tubo |
KR101480564B1 (ko) * | 2008-10-21 | 2015-01-12 | 삼성전자주식회사 | 안면 인식을 이용한 알람 제어 장치 및 방법 |
DE102009001001A1 (de) * | 2009-02-19 | 2010-09-02 | Evonik Degussa Gmbh | Verwendung eines Leitungsrohrs zur Herstellung einer im Wasser verlegten Rohrleitung |
CN102392918A (zh) * | 2011-11-14 | 2012-03-28 | 联塑市政管道(河北)有限公司 | 一种复合pp管及其制备方法 |
FR3044585B1 (fr) * | 2015-12-08 | 2020-01-31 | Arkema France | Structure multicouche comprenant une couche contenant un polymere fluore et copolymere acrylique - procede de fabrication et tube associes |
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GB1065780A (en) * | 1965-02-15 | 1967-04-19 | American Cyanamid Co | Poly(vinylidene fluoride) compositions |
US4288499A (en) * | 1979-05-08 | 1981-09-08 | Rohm And Haas Company | Polymers adherent to polyolefins |
JPH06907B2 (ja) * | 1984-07-16 | 1994-01-05 | 日本石油化学株式会社 | 接着剤 |
JPS63205217A (ja) | 1987-02-23 | 1988-08-24 | Japan Synthetic Rubber Co Ltd | フツ化ビニリデン系樹脂積層体の製造法 |
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US5256460A (en) | 1992-09-14 | 1993-10-26 | Snia Tecnopolimeri S.P.A. | Polymeric blend with high resistance to fuel |
DE4310884A1 (de) * | 1993-04-02 | 1994-10-06 | Huels Chemische Werke Ag | Mehrschichtiges Kunststoffrohr |
FR2711665B1 (fr) | 1993-10-25 | 1995-12-08 | Atochem Elf Sa | Liant d'adhésion du PVDF, son application comme matériau barrière et matériaux obtenus à partir de celui-ci. |
DE4410148A1 (de) | 1994-03-24 | 1995-09-28 | Huels Chemische Werke Ag | Mehrschichtiges Kunststoffrohr |
DE4428414A1 (de) | 1994-08-11 | 1996-02-15 | Huels Chemische Werke Ag | Thermoplastischer Mehrschichtverbund mit guter Schichtenhaftung |
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EP0946362A1 (fr) | 1999-10-06 |
PL334098A1 (en) | 2000-01-31 |
US6964800B2 (en) | 2005-11-15 |
WO1998028131A1 (fr) | 1998-07-02 |
FR2757444B1 (fr) | 1999-02-05 |
CN1244837A (zh) | 2000-02-16 |
DK0946362T3 (da) | 2002-12-16 |
CA2275349C (fr) | 2003-08-12 |
AU5855298A (en) | 1998-07-17 |
ATE227643T1 (de) | 2002-11-15 |
ES2182151T3 (es) | 2003-03-01 |
BR9713778A (zh) | 2000-03-21 |
DE69717142D1 (de) | 2002-12-19 |
PT946362E (pt) | 2003-03-31 |
JP2000507894A (ja) | 2000-06-27 |
JP3367679B2 (ja) | 2003-01-14 |
FR2757444A1 (fr) | 1998-06-26 |
CA2275349A1 (fr) | 1998-07-02 |
DE69717142T2 (de) | 2003-04-24 |
EP0946362B1 (fr) | 2002-11-13 |
US20030008087A1 (en) | 2003-01-09 |
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