CN1063117A - 间二氧杂环戊烯/四氟乙烯共聚物复合材料 - Google Patents
间二氧杂环戊烯/四氟乙烯共聚物复合材料 Download PDFInfo
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- CN1063117A CN1063117A CN91112782.8A CN91112782A CN1063117A CN 1063117 A CN1063117 A CN 1063117A CN 91112782 A CN91112782 A CN 91112782A CN 1063117 A CN1063117 A CN 1063117A
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Abstract
一种气体可透性材料,包括一种具有通过它的连
续孔的材料,孔内涂覆有一种四氯乙烯和全氟-2,2-
二甲基-1,3-间二氧杂环戊烯的共聚物。
Description
本发明涉及疏水和疏油的气体可透性材料。特别是,本发明涉及气体滤器和通气孔,其中滤器或通气孔用一种氟聚物涂覆,使得所形成的材料具有疏水和疏油特性。
对于气体可透性材料来说,人们希望能增强其疏水和疏油特性。四氟乙烯聚合物具有疏水特性是人们公知的,因而它们可用作疏水膜或基质上的疏水涂层。然而,由于一些四氟乙烯聚合物如聚四氟乙烯不是热塑性的且不易溶解,它们很难被涂覆在基质上。它们不能通过使用普通的热塑挤压技术来涂覆。
目前,气体空气滤器和通气孔是由包括多孔聚合物如多孔聚烯烃或聚四氟乙烯的多孔材料制备的。然而,即使用多孔聚四氟乙烯,该材料的疏油性也很差。这种对油渗透的阻力的缺乏妨碍了这种材料在含有一般与周围环境中的油相接触的发动机或装置的应用场合中用作气体通气孔或滤器。
本发明提供的气体可透性材料具有通过该材料的通路或连续孔。该材料被涂覆上含有10~40摩尔百分数的四氟乙烯和90~60摩尔百分数的全氟-2,2-二甲基-1,3-间二氧杂环戊烯的一种无定形共聚物。该涂层至少覆盖孔内部的一部分,但并不完全将孔封住。这样,这种气体可透性材料的气体可透性保持不变,并且该材料可用作气体滤器。所述无定形聚合物涂层的存在使得该材料与无涂层的材料相比变得更为疏油。
气体可透性材料可为任何允许气体特别是空气通过的材料。这种材料含有空隙,所述空隙含有延伸通过该材料的厚度的连续的通路。所述通路在膜片的两侧都是敞开的。这种材料最好是片状、管状或塞状。
气体可透性材料可以是一种织品,如一种无纺织品、纺织品或针织品,或一种条纹稀棉布,只要它具有允许气体或空气流动的空隙或通路或孔。所述材料可以由纸(如滤纸)或合成的或天然的布制成。所述材料还可以是多孔的聚合薄膜或膜,其中的孔形成空隙或通路。“多孔”一词意思是薄膜或膜具有从其一面到另一面通过其整个厚度的连续的孔。作为合成物或聚合物,织物或薄膜可以是聚酰胺、聚酯、聚偏氟乙烯、聚丙烯酸、聚烯烃如聚乙烯和聚丙烯等。
作为一种气体可透性材料优选的是多孔的聚四氟乙烯(PTFE),特别是微孔延展的聚四氟乙烯膜片,如US专利3,953,566所述的具有与纤丝互连的交点的微孔结构的膜片。所得到的微孔或空隙总是允许气体或空气流动,同时对液态水产生阻力。这些多孔PTFE膜优选具有600或更小的Gurley数。
无定形共聚物涂层含有约60~90摩尔百分数的全氟-2,2-二甲基-1,3-间二氧杂环戊烯和40~10摩尔百分数的四氟乙烯。它还可以含有少量的其它共聚用单体。这种共聚物可从杜邦公司得到,称为Teflon AF1600的共聚物,其中间二氧杂环戊烯单元的摩尔百分数约为65%;称为Teflon AF2400的共聚物中间二氧杂环戊烯单元的摩尔百分数约为85%。
这种无定形间二氧杂环戊烯共聚物可方便地以溶液的形式来使用,其中的溶剂为全氟-(2-丁基四氢呋喃)。该溶液应被稀释,这是因为最终的涂层不应盖住和封住通路,以保持该材料的气体可透特性。该溶液优选含有0.01~5.0%(wt/wt)的溶解了的固体。
可以通过任何方便的手段将这种涂层溶液涂加到所述的材料上,并均匀地分散到材料的表面上。可以使用浸泡涂层方法浸渍所述的孔道。然后通过任何方便的手段将溶剂蒸发。
用于形成气体可透性材料的材料可以含有各种其它的附加成份以带给产物特殊的性质或作为一种过程辅助物。例如,这种聚合材料可以包括紫外光稳定剂、抑菌剂、防虫剂、抗静电剂、着色染料、增塑剂等。所述聚合物料还可以包括加工过程中留下的残留物;然而,这些成分通常是少量的,它们对最终产物没有明显的相反作用。
制得的经涂层的材料显示出特别好的疏水和疏油特性,同时还具有良好的空气或气体的通过材料的流动特性。所制得的经涂层的材料可以被用于涉及气体流动的应用场合,其中该材料应能阻滞水、油或类脂乳化液的渗透。这些应用场合包括通气孔或滤器,它们保护用于或靠近自动发动机等的电子设备。还包括有油雾存在时的医用装置的通气孔以及工业过滤的通气孔。
所述经涂层的材料还可用于可被亲代滴液瓶中的油或脂肪物质阻塞的医用通气孔中。
单独的多孔PTFE通常具有很小的疏油性,然而这种带有这里所描述的无定形间二氧杂环戊烯共聚物涂层的材料变成为疏油性材料。
测试方法
Gurley数
使用由W.& L.E.Gurley & Sons制造的Gurley密度计(ASTM D726-58)测量样品对空气流动的阻力。结果以Gurley数表示。Gurley数是在压差为4.88英寸的水柱高的条件下,100立方厘米的空气通过1平方英寸的测试样品所需的时间(以秒计)。
接触角
该试验是测试一种液体在一种固体基质上进行接触的角度。用于完成这种测试的设备是A-100型Rame-Hart十字准线测角计,它由新泽西州的Rame-Hart Mountain Lakes生产。所述设备包括一个望远显微镜测角计、2.0mL测距注射器、注射器支架、带有绿色滤光器的灯、灯孔和透镜以及竖直提升镜台。所用的测试液体为蒸馏水和超重矿物油。测试是在环境条件下进行的。要被测量接触角的样品被切成适于镜合的尺寸,然后将其固定以防止移动。注射器的尖部被固定在样品上方的大约1mm处。灯光集中照射注射器的尖部。使用该注射器时,测试液体被加到样品表面上,直至液滴的直径为约3~4mm时为止。样品上的液滴被置于望远显微测角计的焦点处。调整显微镜的一个十字准线使它与液滴的底部的图像相重合,另一个十字准线对准与沿底线的接触点相交处的弯曲部分的切线。测角器上所读出的两个十字标线间的角度即为接触角。
目视油润湿性
欲测试目视润湿的样品被水平地放到一个平面上。然后将用于确定是否润湿发生的测试液体放到试样的表面上。用一支7.5ml的移液管将测试液体加到样品表面的一小区域内。每个样品上施加大约2~3ml的各种测试液体。首先观察每个样品瞬间的润湿情况。然后在予定的时间间隔,一般为30~60分钟,重新观测样品。所述时间基于试验液体在环境条件下的挥发性,从而使得它们在将样品润湿之前不会完全挥发。用一块有吸收能力的布吸出溶液后表明样品被润湿。完全润湿的区域变成半透明至透明的了。这表明测试液体已进入了样品的孔中。保持它们原有的不透明度的样品表明孔未被填充,从而没有被润湿。
泡点
用异丙醇借助ASTM F316-86测量多孔PTFE的泡点。泡点是使空气通过一层覆盖在PTFE介质上的异丙醇上升时可测得的第一组连续气泡时的压力。这种测量可给出最大孔径的估计值。水进入压力测试方法
按照W.L.Gore与其合作者的584号质量控制测量法测试水进入压力(WEP)。所用的WEP测试仪是由W.L.Gore制造的。试样被夹在一对测试板之间,以防引起损坏。较低的一块板能用水来挤压样品的一部分。将一片pH试纸放到该板间的非加压侧的样品的顶部上作为证明水进入指示标志。然后,以小的增量进行加压,每次加压改变后等10秒钟,直到pH试纸发生颜色变化,表明水进入的第一个信号为止。水突破或进入的压力记录为水进入压力。测量结果应取自测试样品中心以防止出现可能由损坏的边缘部分引起的错误结果。
低于2psi的水进入压力用一种以改进后适于低压的上述WEP测试器为基础的设备来测量。带有pH试纸的样品被置于一个25mm清洁的过滤器夹持器中,该夹持器由Nuclepore Corporation生产,这样膜的一侧可以用水来加压。水柱以渐变的增量加到样品上直至pH试纸的颜色发生变化,记录水柱的高度并转化为psi。
模拟的汗液测试-加重板法
该试验的目的是模拟人的排汗对材料的防水性的影响。该测试是按照M.L.Gore & Associates.Inc的质量控制测试法511号来进行的。将2ml模拟的汗液置于试样两侧,然后将试样在两玻璃板间用4磅重量挤压16小时。然后,将样品冲洗并干燥,再用QCTM501泄漏计在低的流体静压下检测泄漏。在低压力下对样品施加水压。如果发生水的穿透,就断定为泄漏,从而在暴露于模拟的汗液中后,该材料不会保持其防水性。另一方面,如果没有发生穿透,样品没有泄漏,表明防水性保持不变。
模拟的汗液测试-蒸发法
该测试的目的是模拟人体汗液对材料的防水性的影响。测试是按照W.L.Gore & Associates.Inc.的质量控制测试法510号来进行的。一定数量的模拟汗液经蒸发通过置于一设备中的试样。然后冲洗并干燥样品,再用QCTM501泄漏计在低的流体静压下检测它们的泄漏情况。在低压下,对样品施加水压。如果发生水的穿透,就断定为泄漏,从而在暴露于模拟的汗液之后,该材料不会保持其防水性。另一方面,如果没有发生穿透,样品没有泄漏,表明防水性保持不变。
实施例
实例1-应用于多孔膜的涂层
A部分
将0.9845g的四氟乙烯(TFE)和全氟-2,2-二甲基-1,3-间二氧杂环戊烯(PDD)的共聚物,Teflon AF1600无定形氟聚物(65mol%的PDD)放入200g被称为Fluoroinert-75或FC-75的全氟(2-丁基四氢呋喃)中,得到含量为0.49%(wt)的涂覆溶液。该混合物被浸入一超声波浴器中以促进Teflon AF的溶解。
将一种多孔的聚四氟乙烯膜(由W.L.Gore & Associates得到)展开并固定在一个绣花箍子上,使张力均匀地施加到膜上。将膜拉紧以防止由于接触溶剂以及后来溶剂的挥发而引起的皱折。在箍中的膜被置于一个捕集盘上方并倾斜至45°固定。用一支7.5ml的移液管将Teflon AF溶液大量地涂加到膜上,并用一玻璃棒使之分散,直至整个膜被润湿(即孔内已进入溶液,通常不透明的PTFE膜变得透明)。过量的溶液滴入盘中。然后将箍中的经涂层的膜竖直悬置在通风橱中20分钟以干燥该涂层膜。然后将该涂层膜从箍中取出。
一片经涂层的膜即样品A,泡点约为15~20psi,是被固定在一个7英寸的绣花箍上的。
另一片经涂层的膜即样品B,泡点超过50psi,是被固定在一个10英寸的绣花箍上的。
B部分
在199.98g FC-75中溶解0.9916g Teflon AF1600制得一种0.493% wt/wt的涂覆溶液。用一种磁性搅拌器来搅拌此混合物,以便Teflon AF溶解。按照与A部分中所述的用于样品A相同的方法将该溶液涂加到多孔的PTFE上。使用7英寸的绣花箍。该经涂层的膜称为样品C。
测试这些膜并与未处理过的,即未涂层的膜相比较,结果如下:
处理过的样品 未处理的样品(对照物)
样品A 0.490%
wt/wt溶液
Gurley数(秒) 16.5±0.4 15.8±1.8
接触角(°)
H2O(蒸馏水) 154.1,152.8*128.1
油(矿物油) 121.7,118.8*72.2±2.0
*每个表面一个测量值。
样品B 0.490%
wt/wt溶液
Gurley数(秒) 363±10 342±3
接触角(°)
H2O(蒸馏水) 120.1,126.2*154.2
油(矿物油) 97.3,71.1*52.2±3.5
样品C 0.493%
wt/wt溶液
目测的油润湿性
马达油(10w/ 30分钟或更少时间内
30) 45分钟后未润湿 润湿
传动油 30分钟或更少时间内
(Dexron Ⅱ) 45分钟后未润湿 润湿
*每个表面一个测量值。
样品A和B的接触角测量值表明,Teflon AF涂层使它们产生了疏油性。这一点进一步由样品C所证实,未处理过的对照物在仅仅30分钟或更少的时间内就被润湿了,而样品C甚至在45分钟后仍可抑制马达油和传动油而不被润湿。然而,Gurley数的测量值表明,样品A和B在它们抵抗空气流动的能力上没有显著的改变,这表明涂加的Teflon AF涂层是少量的。
实例2-涂加到聚酯滤网上的涂层
按照实例1的A部分所述的方法制备一种Teflon AF1600溶液。
将一块硬聚酯正方形织物滤网放入一个150mm直径的皮特里培养皿中,该滤网每厘米47.2个网孔,厚0.0144cm,重0.00664g/cm2,它是由Tetko Inc.生产的Tetko 滤网。用一个7.5ml的移液管将上述制得的溶液大量地涂加到网上,直至整个滤网被覆盖上一层薄薄的溶液。然后,用镊子将滤网翻动以确保滤网的间隙空间被填充入溶液。
然后,将网竖直悬挂在一通风橱中20分钟以蒸发掉溶剂。这张干燥的经过处理的网(样品)D和一张未处理过的来源相同的网被测试并作比较,结果如下:
结果:
处理过的网 未处理过的样品网(对照物)
样品D 0.490%
wt/wt溶液
接触角(°)
H2O(蒸馏水) 135.2,135.7*0
油(矿物油) 121.1,122.2*0
*每个表面一个测量值。
正如样品D的接触角测量值所表明的,Teflon AF涂层将曾是完全亲水和亲油的滤网转变为疏水和疏油的材料。
实例3-涂加于滤纸的涂层
A部分
按照实例1的A部分所述的方法制备一种Teflon AF1600溶液。将一块直径为150mm型号为#50的硬Whatman滤纸样品圆板(由Whatman Ltd.生产)放在一个150mm的皮特里培养皿中。按照实例2的方法涂加溶液,按实例2的方法将该经涂层的纸干燥。
干燥后的滤纸称作样品E。
B部分
按照实例1的B部分所述的方法制备一种涂覆溶液,并涂加到与本实例的A部分所用的相同类型的滤纸上,涂加步骤与A部分所采用的相同。该样品被称为样品F。第二批标为样品G。
这些样品与未经处理的,即未涂覆的样品一起被测试并进行比较,得到如下结果:
处理过的样品 未经处理过的样品(对照物)
样品E 0.490%
wt/wt溶液
接触角(°)
H2O(蒸馏水) 139.5,147.7*0
油(矿物油) 94.2,95.7*0
处理过的样品 未经处理过的样品(对照物)
样品F 0.493%
wt/wt溶液
水进入压(psi) 0.8±0.05 0psi
无γ射线照射
处理过的样品 未经处理过的样品(对照物)
样品G 0.493%
wt/wt溶液
水进入压(psi) 0.9±0.1 未测
经γ射线照射
5.0Mrad
样品E的接触角测量值表明,Teflon AF涂层将亲水和亲油的纸转变为疏水和疏油的材料。这一点也可由样品F测得的WEP值的增加看出来,对照样品的WEP值为0。
受到5.0Mrads γ射线照射的样品G说明了照射Teflon AF涂层不会导致增加WEP值的能力的破坏。由于在辐射处理以前滤纸的WEP为0,所以未测对照物样品的WEP值。
实例4-涂加于尼龙膜过滤器的涂层
A部分
按照实例1的A部分所述的方法制备一种Teflon AF1600溶液。将从Gelman Sciences,Inc.得到的两块Nylaflo 尼龙膜过滤器圆盘样品分别放置在直径为150mm的皮特里培养皿中。圆盘直径为142mm,孔径为0.2μm数量级。完全按照实施例2的方法将溶液涂加到尼龙膜上,涂层膜按例2的方法干燥,它们被称为样品H。
B部分
按照实例1的B部分所述的方法制备涂覆溶液,并将其涂加到与本实例的A部分所述的相同类型的膜上。以相同的方法制备三个样品,称为I、J和K。
结果:
处理过的样品 未处理过的样品(对照物)
样品H 0.490%
wt/wt溶液
接触角(°)
H2O(蒸馏水) 145.5,135.2*0
油(矿物油) 107.1,91.1*0
*每个表面一个测量值。
模拟汗液测试
加重板法 无泄漏 泄漏
样品I 0.493% wt/wt溶液
水进入压(psi)
未用γ射线照射 49±3 0
处理过的样品 未处理过的样品(对照物)
样品J 0.493%
wt/wt溶液
水进入压(psi) 24±1 未测
5.0Mrad
γ射线照射
样品K 0.493% wt/wt溶液
模拟汗液测试
蒸发法 无泄漏 泄漏
样品H的接触角测量值表明,Teflon AF涂层将曾为亲水和亲油的尼龙膜转变成疏油和疏水的材料。这一点可进一步由样品I的WEP值的增加来证实,对比物的WEP为0。
受到5.0Mrads γ射线照射的样品J表明,照射没有损害Teflon AF涂层的增加WEP值的能力。样品J的WEP值低于样品I,这可能是由于照射过的尼龙强度变弱的缘故。结果是,样品J在WEP测试期间裂开了。从而所记录的WEP不是所定义的真正的WEP。由于尼龙膜在照射处理前的WEP为0,因而没有测试对照样品的WEP值。
样品H和K的模拟汗液测试结果表明,Teflon AF涂层在与人的汗液接触后使尼龙能抵抗水的渗透。这表明多孔材料的Teflon AF处理可以提供防水屏障或结构,它的抗水能力不会在接触人汗以后遭到损害。
实例5-涂加于多孔PTFE/PVC网状层压板的涂层
在由延展的PTFE和PVC网组成的复合层压板上实行涂覆步骤。将0.30g Teflon AF1600放入61.87g FC-75中制得0.48%wt/wt的涂覆溶液。该混合物被浸在超声波浴器中以促进Teflon AF的溶解。具有0.45μm起始孔径的多孔PTFE样品(由W.L.Gore & Associates.Inc.得到)被层压到聚氯乙烯(PVC)上。该层压板被切成102mm的圆盘。圆盘被放入150mm直径的皮特里培养皿中。由于PVC支撑,层压的PTFE保持刚性,因而不需要因承受拉力而固定样品。用一支7.5ml的移液管按照与实例2相同的方式将溶液大量地涂加到到圆盘上。
标为样品L、M、N、O的四个该样品被测试并与未处理的样品比较,结果如下:
处理过的样品 未经处理的样品(对照物)
样品L 0.48%wt/wt溶液
加入重量百分数 2.45 未加
Gurley数(秒) 6.7 6.7±0.4
动力转向流体的
目测润湿
膜侧 30分钟后未润湿 30分钟内润湿
支撑侧 30分钟后未润湿 30分钟内润湿
处理过的样品 未经处理的样品(对照物)
样品M 0.48%wt/wt溶液
加入重量百分数 2.69 未加
Gurley数(秒) 7.5 6.7±0.4
传动流体(DexronⅡ)
的目测润湿
膜侧 30分钟后未润湿 30分钟内润湿
支撑侧 30分钟后未润湿 30分钟内润湿
样品N 0.48%wt/wt溶液
加入重量百分数 2.59 未加
Gurley数(秒) 6.7 6.7±0.4
机油(10W/30)
的目测润湿
膜侧 30分钟后未润湿 30分钟内润湿
支撑侧 30分钟后未润湿 30分钟内润湿
样品0 0.48%wt/wt溶液
加入重量百分数 2.27 未加
Gurley数(秒) 6.6 6.7±0.4
制动流体的
目测润湿
膜侧 30分钟后未润湿 30分钟内润湿
支撑侧 30分钟未润湿 30分钟内润湿
样品L、M、N、O给出了涂在每个样品上的Teflon AF的低重量百分数增加的实例。由Gurley数的结果可以进一步看出,所有样品对空气流动的阻力没有受到显著的影响,这表明Teflon AF涂层没有堵塞孔结构。另一方面,虽然涂覆量较小,这些样品较之未处理过的对照物仍显示出显著的疏油性,这可参照目测润湿测试的结果看出。在所有情况下,对照物在30分钟或更短的时间内与各种油都变润湿,而经Teflon AF涂层的样品在45分钟后仍可抑制油的润湿。
实例6-涂加到尼龙塔夫绸织物上的涂层
将3.56g Teflon AF 1600溶解到698.70g FC-75中制得一种0.507% wt/wt的涂覆溶液。该混合物被浸入一超声波浴器中以加速Teflon AF的溶解。将一块纯的成品尼龙塔夫绸织物放入150mm直径的皮特里培养皿中。用一支7.5ml的移液管将上述溶液大量地涂加到尼夫塔夫绸上,直至整个织物被盖上一薄层溶液。用镊子翻动尼龙织物以确保塔夫绸的间隙空间均填充到溶液。
然后,将尼龙织物竖直悬挂在通风橱中20分钟以使溶剂挥发掉。这种干燥的经处理过的塔夫绸织物(样品Z)和同一来源未处理过的塔夫绸织物一起被测试并作比较,结果如下:
所用的尼龙塔夫绸由Duro Finishing of Fall River,Massachusetts生产,它的定量为1.7盎司/平方码(OZ/square yard),径向上每英寸106根纱,纬向上每英寸86根纱,纱线为70但尼尔。
处理过的样品 未处理过的样品(对比物)
样品Z 0.507%
wt/wt溶液
加入重量百分数 1.25 未加
Gurley数(秒) 0.25±0.01 0.25±0.02
目测油润湿
马达油(10w/30) 1小时后未润湿 瞬间润湿
传动油(DexronⅡ) 1小时后未润湿 瞬间润湿
由目测油润湿测试结果看出,曾是亲油的样品Z变成了疏油的了。而这仅仅是通过很小重量百分数的加入的结果,即仅涂覆了薄薄的一层。这一点可进一步由Gurley数测量值证实,样品Z在它的抑制空气流动的能力上没有显著改变。
Claims (5)
1、一种含有通过该材料的通路的气体可透性材料,至少在一部分通路的内部,所述材料含有一种包括10~40摩尔百分数的四氟乙烯和相应90~60摩尔百分数的全氟-2,2-二甲基-1,3-间二氧杂环戊烯的无定形共聚物。
2、按权利要求1所述的气体可透性材料,其特征在于所述材料是一种选自纺织品、无纺织品、针织品的板片,具有微孔结构的多孔聚合板,纤维素纸和玻璃纤维纸。
3、按权利要求2所述的气体可透性材料,其特征在于所述材料是多孔PTFE。
4、按权利要求1的气体可透性材料,其特征在于所述材料是塞形的。
5、按权利要求1的气体可透性材料,其特征在于所述材料是管形的。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/621,661 US5116650A (en) | 1990-12-03 | 1990-12-03 | Dioxole/tfe copolymer composites |
US621,661 | 1990-12-03 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1063117A true CN1063117A (zh) | 1992-07-29 |
CN1030283C CN1030283C (zh) | 1995-11-22 |
Family
ID=24491091
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN91112782.8A Expired - Lifetime CN1030283C (zh) | 1990-12-03 | 1991-12-02 | 间二氧杂环戊烯/四氟乙烯共聚物复合材料 |
Country Status (8)
Country | Link |
---|---|
US (1) | US5116650A (zh) |
EP (1) | EP0561875B1 (zh) |
JP (1) | JP3390004B2 (zh) |
CN (1) | CN1030283C (zh) |
AU (1) | AU643860B2 (zh) |
CA (1) | CA2093518C (zh) |
DE (1) | DE69107861T2 (zh) |
WO (1) | WO1992009353A1 (zh) |
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- 1991-11-19 DE DE69107861T patent/DE69107861T2/de not_active Expired - Lifetime
- 1991-11-19 WO PCT/US1991/008629 patent/WO1992009353A1/en active IP Right Grant
- 1991-11-19 AU AU90732/91A patent/AU643860B2/en not_active Expired
- 1991-11-19 JP JP50196792A patent/JP3390004B2/ja not_active Expired - Lifetime
- 1991-11-19 EP EP92900432A patent/EP0561875B1/en not_active Expired - Lifetime
- 1991-12-02 CN CN91112782.8A patent/CN1030283C/zh not_active Expired - Lifetime
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100334120C (zh) * | 2002-07-12 | 2007-08-29 | 东华大学 | 含杂环结构的氟树脂、制造方法及其用途 |
CN110240682A (zh) * | 2019-05-29 | 2019-09-17 | 浙江大学 | 一种含全氟-2,2-二甲基-1,3-二氧杂环戊烯的嵌段共聚物的制备方法 |
CN110240682B (zh) * | 2019-05-29 | 2021-11-09 | 浙江大学 | 一种含全氟-2,2-二甲基-1,3-二氧杂环戊烯的嵌段共聚物的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
DE69107861T2 (de) | 1995-07-06 |
CA2093518C (en) | 1996-07-02 |
US5116650A (en) | 1992-05-26 |
DE69107861D1 (de) | 1995-04-06 |
AU9073291A (en) | 1992-06-25 |
JP3390004B2 (ja) | 2003-03-24 |
CA2093518A1 (en) | 1992-06-04 |
JPH06505914A (ja) | 1994-07-07 |
AU643860B2 (en) | 1993-11-25 |
WO1992009353A1 (en) | 1992-06-11 |
EP0561875A1 (en) | 1993-09-29 |
EP0561875B1 (en) | 1995-03-01 |
CN1030283C (zh) | 1995-11-22 |
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