CN103290687B - 纤维结构体、其制造方法和用途以及纤维-树脂复合材料 - Google Patents
纤维结构体、其制造方法和用途以及纤维-树脂复合材料 Download PDFInfo
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Abstract
本发明涉及经固定和/或稳定的纤维结构体,所述纤维结构体来自纤维材料以及用于使该纤维材料固定和稳定的试剂。用于固定和稳定的试剂是统计结构共聚酯,该统计结构共聚酯由二酸组分(对苯二甲酸和任选的间苯二甲酸)以及二醇组分(丁二醇、二甘醇和三甘醇)形成。本发明还提供了制造该纤维结构体的方法。将该纤维结构体用作聚合物基质(特别是环氧树脂)的增强材料。此外,本发明还提供了包含至少一种热固性树脂以及本发明所述纤维结构体的纤维复合材料。
Description
技术领域
本发明涉及经固定和/或稳定的纤维结构体,该结构体来自纤维材料以及用于使纤维材料固定和稳定的试剂。用于固定和稳定的试剂是统计结构共聚酯(statisticalcopolyester),该统计结构共聚酯由二酸组分(对苯二甲酸和任选的间苯二甲酸)以及二醇组分(丁二醇、二甘醇和三甘醇)形成。本发明还提供了制造该纤维结构体的方法。将该纤维结构体用作聚合物基质(特别是环氧树脂)的增强材料。此外,本发明还提供了包含至少一种热固性树脂以及本发明所述纤维结构体的纤维复合材料。
背景技术
由纤维复合材料制成的材料具有高的强度质量比,广泛应用于对强度、耐腐蚀性和轻的重量有要求的领域。因此,可容易地将此类纤维-树脂复合材料用于例如航空航天的组件中。这些复合材料同样特别适用于运动装备制品,如网球拍或高尔夫球棒。
增强单元(reinforcement element)以如下形式存在于这些复合材料中:单向丝状形式或面状形式,如纤维网、织物(woven fabric)或纤维无纺布。
处于丝状或网状形式的纤维、织物或无纺布必须加以固定和稳定,其起到了简化操作的作用,并使得单个面状结构体或多个这种面状结构体通过温度或压力的作用得以粘合。通过温度和压力的影响,同样可对待预成型的、经固定或粘合的单层或多层面状结构体的稳定预成型加以控制。
然后,将以这一方式制造和预处理的增强材料嵌入聚合物基质中。在这方面,增强材料和聚合物基质之间的粘附特别重要。
由EP1705269A1中已知的热塑性纤维材料是由包含聚羟基醚的原材料纺成。在将增强纤维嵌入聚合物基质前,将这些来自聚羟基醚的纤维用作增强纤维的固定线(fixingthreads)。
此外,由EP0698649A2中已知的共聚酯热熔融粘附物质显示出杰出的粘合性、低的熔点、快速的结晶作用以及对洗涤和清洁具有良好的抵抗力。
发明内容
由此开始,本发明的目的在于提供稳定性得以改善的纤维结构体。
通过具有权利要求1所述特征的纤维结构体以及通过该纤维结构体的制造方法满足了这一目的。通过具有权利要求11所述特征的纤维-树脂复合材料同样实现了该目的。在权利要求15中阐述了本发明所述纤维结构体的用途。
本发明提供了经固定和/或稳定的纤维结构体,所述纤维结构体来自纤维材料以及使该纤维材料固定和稳定的试剂。
本发明所述的用于固定和稳定的试剂是统计结构共聚酯,所述统计结构共聚酯由下述组分形成:
55-100mol%对苯二甲酸;
0-45mol%间苯二甲酸;
35-75mol%丁二醇;
15-35mol%二甘醇;
10-30mol%三甘醇。
在这方面,相对于总二酸和总二醇的量各自为100mol%而言,对苯二甲酸和丁二醇的摩尔分数之和最多为150mol%。
所述至少一种统计结构共聚酯优选由下述组分形成:
70-100mol%、优选85-100mol%对苯二甲酸;
0-30mol%、优选0-15mol%间苯二甲酸;
45-65mol%、优选47-57mol%丁二醇;
20-30mol%、优选23-28mol%二甘醇;
15-25mol%、优选20-25mol%三甘醇。
在这方面,相对于总二酸和总二醇的量各自为100mol%而言,对苯二甲酸和丁二醇的摩尔分数之和最多为150mol%。
在优选的实施方式中,在共聚酯和添加剂之和为100wt%的情况下,所述至少一种统计结构共聚酯可以包含0-2wt%、优选0.05-1wt%的添加剂,特别是成核剂、稳定剂、润滑剂、消泡剂、缩合催化剂或上述物质的混合物。
本发明所使用的共聚酯在160℃、2.16kg载重下,根据ISO/DIN1133测量的优选熔融粘度范围为100-3000Pas、优选100-600Pas、特别优选120-500Pas、更特别优选150-300Pas。
如果本发明所述的共聚酯以固定线(例如作为纤维纱、复丝或单丝)的形式加以使用,其在160℃、2.16kg载重下,根据ISO/DIN1133测量的优选熔融粘度范围为1000-3000Pas、优选1500-2500Pas、特别优选1700-2200Pas。
本发明所使用的共聚酯在加热速率为20K/min下,根据ISO11357测量的优选熔点范围为60-160℃、优选70-150℃、特别优选90-140℃。
优选根据如下合成来进行共聚酯的制造。
将芳香二羧酸或二羧酸混合物分散于二醇中,加入酯化催化剂和任选的合适的热稳定剂,以过量5-50mol%来使用二醇。在200-280℃、优选210-260℃的温度范围内随着缓慢升温进行酯化反应。在这一过程中蒸馏出所生成的水。
随后,在220-270℃、优选230-260℃的温度范围内,任选在缩聚催化剂(1-100ppm、优选10-45ppm,相对于聚酯的量)存在的情况下,在非活化的(inertized)高压釜中进行缩聚反应。在这方面,逐步施加真空,将过量的二醇抽取出直至低于1mbar的最终真空中。到达期望的粘度后,将所生成的聚酯移出、制粒并干燥。
可将金属Mn、Zn、Ca、Sn、Ti或Mg与例如低级脂肪醇(如丁醇)的盐用作酯化催化剂。基于锑、钛、锡或锗的化合物(例如三氧化锑)适于作为缩聚催化剂。酯化催化剂和缩聚催化剂均被广大技术人员所熟悉。
纤维材料可优选包含单向丝或面状纤维材料、或实质上由单向丝或面状纤维材料构成,所述面状纤维材料选自下组:纺织品(fabrics)、绒织物(fleeces)、针织网(knittedmeshes)或针织物(knitted fabrics)、或者无纺布。丝和面状纤维材料的组合也同样可以。
纤维材料优选选自包括如下纤维的组:
玻璃纤维;
碳纤维;
矿物纤维;
合成纤维,特别是聚合物纤维,优选聚酯纤维和聚酰胺纤维、特别是聚芳酰胺纤维;
天然纤维,特别是棉花、羊毛、木棉、大麻、亚麻、黄麻或木材;以及
上述纤维的混合物。
本发明提供了制造上述纤维结构体的方法,其中,将至少一种用于固定和稳定纤维材料的试剂通过粉点涂覆(powder point coating)、浆点涂覆(paste point coating)或分散涂覆(scatter coating)施用至纤维材料,或者作为浆状物(paste)、悬浮物(suspension)、膜状物(film)、网状物(web)、无纺布、固定无纺布或织物(fixed nonwovenor woven fabric)或喷射熔融物(sprayed melt)施用至纤维材料;随后,通过温度和/或压力的作用进行纤维结构体的固定。
或者,通过使用由至少一种统计结构共聚酯制成的固定线加以缝合来进行所述固定。在这一过程中,无需后续的温度和/或压力的作用即已完成所述固定。
分散涂覆或者作为浆状物、悬浮物、膜状物、网状物或喷射熔融物或缝合进行施加都是优选的施用方法。特别优选通过分散涂覆、网状物、喷射熔融物或缝合进行施用。
本发明另一方面涉及纤维-树脂复合材料,所述纤维-树脂复合材料包含至少一种热固性树脂和至少一种前述纤维结构体。
热固性树脂优选为环氧树脂。
出乎意料地发现,就用于通过以本发明所述的共聚酯加以固定来嵌入的聚合物基质而言,粘附性得到改善。
在23℃的测量温度下,在根据ASTM D2344M的层间剪切强度(ILSS)试验中,纤维-树脂复合材料优选具有至少55MPa、优选至少60MPa的强度。
此外,在根据AITM1.0010的冲击后压缩强度(CAI)试验中,优选本发明所述的纤维-树脂复合材料具有至少185MPa、优选至少210MPa、特别优选至少240MPa的冲击后压缩强度。
本发明又一方面涉及前述纤维结构体作为环氧树脂增强材料的用途,特别是在运动、休闲、机械工业、电子学、建筑业、医学工程、交通和运输工具、以及航空航天工程领域中的用途。
前述纤维结构体作环氧树脂增强材料的用途特别优选用于运动、休闲、机械工业、交通和运输工具、以及航空航天工程领域。
具体实施方式
参考下述实施例将更加详细地描述本发明的主题,而本发明的主题并不限于本文所示的具体实施方式。
本发明所述共聚酯的组成(组分(A1)-(A4))以及对照体系的组成(CoPES I、CoPESII、EVA、PA6/12/66、PA12、PE)在表1示出。
表1
*在160℃、2.16kg载重下的熔融粘度
**在160℃、2.16kg载重下的熔融流动速率
***在190℃、2.16kg载重下的熔融流动速率
还可用Melthene MX06替换Melthene MX09。
根据下述标准在如下样品上进行试验和测量。
张力剥离试验
DIN54310
测量温度23℃
样品的制造
将待测试的热塑性塑料平膜(每单位面积涂层重量为200g/m2)借助于双带式压机层压至聚酯-毛织物上(55/45wt%,褐色,每单位面积涂层重量为210g/m2,制造商:德国Becker Tuche或意大利Marzotto)。在这方面,层压温度为高于热塑性塑料熔点30℃。在50℃储存24h后,切下24×8cm的样品。将塑料框(15×5cm)放至该样品上,同时将蜡纸带放于该样品的窄边下。将所述框用新配制的、经脱气的环氧化物混合物填充至3mm的水平。将所述环氧化物于23℃下硬化12-16h。然后,移除所述框。蜡纸带使得所述热塑性塑料膜与所述环氧化物分开约3cm长。
环氧化物由环氧值为0.520-0.550eq./100g的双酚A环氧树脂(Grilonit C1302,EMS-CHEMIE AG)和胺值为290-350mg KOH/g的胺硬化剂(Grilonit H84048,EMS-CHEMIEAG)以2:1的重量比混合而成。层间剪切强度(ILSS)的测定
ASTM D2344M
测量温度:23℃和80℃
样品的制造
首先,通过树脂传递模塑工艺(RTM)制造尺寸为330×330×4mm的板。出于这一目的,将每单位面积涂层重量为298g/m2的单向碳纤维丝手动放置于已预加热至80℃的可加热压机(heatable press)的模塑腔中,使用筛子将18g热塑性塑料粉末均匀地分散在所述单向碳纤维丝上;将这一过程重复15次,相对于第一层单向碳纤维丝,第二层单向碳纤维丝旋转-45°,第三层旋转+45°,第四层旋转90°。因此,16层结构体的第五层与第一层的方向相同。除第16层外,18g热塑性塑料粉末分布于每一层。关闭模具后,在真空(残余压力为0.05mbar)下加热至120℃,当达到所述温度时,向其中倒入已预加热至80℃的单组分环氧树脂(来自Hexcel Corporation(美国)的HexFlow RTM6)。在180℃、6bar的压力下硬化90min。随后,降低压力并同时进行冷却。保持所述真空度至模具打开。将来自Toho TenaxCo.(日本)的IMS60E13用作单向碳纤维丝。在使用超声对板进行质量检测后,将样品切割为24×8×4mm的尺寸。在测量前,将样品置于测量温度下60min。在人工气候室(climatechamber)内进行压力测试。
用于对照试验的样品据此制造,但是在碳纤维丝之间中不加入任何热塑性塑料粉末。
冲击后压缩强度(CAI)的测定
AITM1.0010(Airbus标准)
测量温度:23℃
样品的制造
板的制造如同ILSS试验中所述。在使用超声进行质量检测后,将样品切割为150×100×4mm的尺寸。
用于对照试验的样品据此制造,但是在碳纤维丝之间不加入任何热塑性塑料粉末。
在强度试验前,使用落塔(drop tower)施加30J的冲击。使用超声测定由在这一冲击所产生的分层面积(delamination area)。随后,在相同样品上测量剩余强度并将其作为压缩强度。
熔融粘度(MV)或熔融流动速率(MFR):
ISO1133
颗粒化
熔点
ISO标准11357
颗粒化
在升温速率为20K/min下实施差示扫描量热法(DSC)。给出了最大峰值处的温度。
使用本发明所举出的材料和对照材料进行关于材料性质的对照试验。
在这方面,张力剥离试验的结果在表2中示出。
表2
实施例 | 热固性塑料 | 粘力值[N/5cm] |
1 | CoPES(A1) | 132 |
2 | CoPES(A2) | 149 |
3 | CoPES(A3) | 150 |
4 | CoPES(A4) | 128 |
对照例 | ||
5 | CoPESI | 25 |
6 | CoPESII | 11 |
7 | EVA | 34 |
8 | PA6/12/66 | 7 |
9 | PA12 | 1 |
10 | PE-LD | 1 |
比起非本发明所述的共聚酯、乙烯-乙酸乙烯酯、不同的聚酰胺或低密度的PE作为热固性塑料(对照例5-10)所实现的粘力值,本发明所述共聚酯(A1)-(A4)(实施例1-4)所得到的粘力值为至少3.7倍高。因此,仅对本发明所述的共聚酯进行了下述测试。
层间剪切强度(ILSS)试验的结果在表3中示出。
表3
在23℃和80℃的测量温度下,相比于无本发明所述共聚酯的复合材料(对照例15),由于使用了本发明所述的共聚酯,实施例11-14显示出复合材料具有增高的强度。
冲击后压缩强度(CAI)试验的结果在表4中示出,即,在之前的30J冲击并由于所述冲击出现分层面积后,对样品的压缩强度进行测量。
表4
实施例 | 热固性塑料 | CAI[MPa] | 分层面积[mm2] |
16 | CoPES(A1) | 255 | 890 |
17 | CoPES(A2) | 259 | 850 |
18 | CoPES(A3) | 258 | 860 |
19 | CoPES(A4) | 253 | 900 |
对照例 | |||
20 | w/o | 153 | 6050 |
相比于无本发明所述共聚酯的复合材料(对照例20),由于使用了本发明所述的共聚酯,实施例16-19显示出复合材料具有显著增高的强度,并且具有实质上更小的分层面积。
Claims (34)
1.一种纤维-树脂复合材料,所述纤维-树脂复合材料包含至少一种热固性树脂以及至少一种经固定和/或稳定的纤维结构体,所述纤维结构体来自纤维材料以及用于使所述纤维材料固定和稳定的试剂,其特征在于,所述用于固定和稳定的试剂是由下述组分所形成的至少一种统计结构共聚酯:
55-100mol%对苯二甲酸;
0-45mol%间苯二甲酸;
35-75mol%丁二醇;
15-35mol%二甘醇;
10-30mol%三甘醇;
其中,相对于总二酸和总二醇的量各自为100mol%而言,对苯二甲酸和丁二醇的摩尔分数之和最多为150mol%,
所述至少一种热固性树脂起到聚合物基质的作用。
2.如权利要求1所述的纤维-树脂复合材料,其特征在于,所述至少一种统计结构共聚酯由下述组分形成:
70-100mol%对苯二甲酸;
0-30mol%间苯二甲酸;
45-65mol%丁二醇;
20-30mol%二甘醇;
15-25mol%三甘醇;
其中,相对于总二酸和总二醇的量各自为100mol%而言,对苯二甲酸和丁二醇的摩尔分数之和最多为150mol%。
3.如权利要求2所述的纤维-树脂复合材料,其特征在于,所述至少一种统计结构共聚酯由下述组分形成:
85-100mol%对苯二甲酸;
0-15mol%间苯二甲酸;
47-57mol%丁二醇;
23-28mol%二甘醇;
20-25mol%三甘醇;
其中,相对于总二酸和总二醇的量各自为100mol%而言,对苯二甲酸和丁二醇的摩尔分数之和最多为150mol%。
4.如在先任一项权利要求所述的纤维-树脂复合材料,其特征在于,在共聚酯和添加剂之和为100wt%的情况下,所述至少一种统计结构共聚酯包含0-2wt%的所述添加剂。
5.如权利要求4所述的纤维-树脂复合材料,其特征在于,在共聚酯和添加剂之和为100wt%的情况下,所述至少一种统计结构共聚酯包含0.05-1wt%的所述添加剂。
6.如权利要求4所述的纤维-树脂复合材料,其特征在于,所述添加剂选自于成核剂、稳定剂、润滑剂、消泡剂、缩合催化剂。
7.如权利要求1-3中任一项所述的纤维-树脂复合材料,其特征在于,所述至少一种共聚酯在160℃、2.16kg载重下,根据ISO/DIN 1133测量的熔融粘度范围为100-3000Pa· s。
8.如权利要求7所述的纤维-树脂复合材料,其特征在于,所述至少一种共聚酯在160℃、2.16kg载重下,根据ISO/DIN 1133测量的熔融粘度范围为100-600Pa· s。
9.如权利要求7所述的纤维-树脂复合材料,其特征在于,所述至少一种共聚酯在160℃、2.16kg载重下,根据ISO/DIN 1133测量的熔融粘度范围为120-500Pa· s。
10.如权利要求7所述的纤维-树脂复合材料,其特征在于,所述共聚酯在160℃、2.16kg载重下,根据ISO/DIN 1133测量的熔融粘度范围为150-300Pa· s。
11.如权利要求1-3中任一项所述的纤维-树脂复合材料,其特征在于,所述至少一种共聚酯作为固定线存在,并且在160℃、2.16kg载重下,根据ISO/DIN 1133测量的熔融粘度范围为1000-3000Pa· s。
12.如权利要求11所述的纤维-树脂复合材料,其特征在于,所述至少一种共聚酯作为固定线存在,并且在160℃、2.16kg载重下,根据ISO/DIN 1133测量的熔融粘度范围为1500-2500Pa· s。
13.如权利要求11所述的纤维-树脂复合材料,其特征在于,所述至少一种共聚酯作为固定线存在,并且在160℃、2.16kg载重下,根据ISO/DIN 1133测量的熔融粘度范围为1700-2200Pa· s。
14.如权利要求1-3中任一项所述的纤维-树脂复合材料,其特征在于,所述至少一种共聚酯在加热速率为20K/min下,根据ISO 11357测量的熔点范围为60-160℃。
15.如权利要求14所述的纤维-树脂复合材料,其特征在于,所述至少一种共聚酯在加热速率为20K/min下,根据ISO 11357测量的熔点范围为70-150℃。
16.如权利要求14所述的纤维-树脂复合材料,其特征在于,所述至少一种共聚酯在加热速率为20K/min下,根据ISO 11357测量的熔点范围为90-140℃。
17.如权利要求1-3中任一项所述的纤维-树脂复合材料,其特征在于,所述纤维材料为单向丝或面状纤维材料,所述面状纤维材料选自下组:纺织品、无纺布或者上述面状纤维材料的组合。
18.如权利要求17所述的纤维-树脂复合材料,其特征在于,所述纺织品选自于绒织物和针织物。
19.如权利要求18所述的纤维-树脂复合材料,其特征在于,所述针织物为针织网。
20.如权利要求1-3中任一项所述的纤维-树脂复合材料,其特征在于,所述纤维材料选自包括如下纤维的组:
玻璃纤维;
碳纤维;
矿物纤维;
合成纤维;
天然纤维;以及
上述纤维的混合物。
21.如权利要求20所述的纤维-树脂复合材料,其特征在于,所述合成纤维为聚合物纤维。
22.如权利要求20所述的纤维-树脂复合材料,其特征在于,所述合成纤维为聚酯纤维和聚酰胺纤维。
23.如权利要求20所述的纤维-树脂复合材料,其特征在于,所述合成纤维为聚芳酰胺纤维。
24.如权利要求20所述的纤维-树脂复合材料,其特征在于,所述天然纤维为棉花、羊毛、木棉、大麻、亚麻、黄麻或木材。
25.如权利要求1-3中任一项所述的纤维-树脂复合材料,其特征在于,所述至少一种热固性树脂为环氧树脂。
26.如权利要求1-3中任一项所述的纤维-树脂复合材料,其特征在于,在23℃的测量温度下,在层间剪切强度试验中,所述纤维-树脂复合材料具有至少55MPa的强度。
27.如权利要求26所述的纤维-树脂复合材料,其特征在于,在23℃的测量温度下,在层间剪切强度试验中,所述纤维-树脂复合材料具有至少60MPa的强度。
28.如权利要求1-3中任一项所述的纤维-树脂复合材料,其特征在于,在冲击后压缩强度(CAI)试验中,所述纤维-树脂复合材料具有至少185MPa的冲击后压缩强度。
29.如权利要求28所述的纤维-树脂复合材料,其特征在于,在冲击后压缩强度(CAI)试验中,所述纤维-树脂复合材料具有至少210MPa的冲击后压缩强度。
30.如权利要求28所述的纤维-树脂复合材料,其特征在于,在冲击后压缩强度(CAI)试验中,所述纤维-树脂复合材料具有至少245MPa的冲击后压缩强度。
31.制造权利要求1-30中任一项所述纤维-树脂复合材料的方法,其中,将至少一种用于使纤维材料固定和稳定的试剂通过粉点涂覆、浆点涂覆或分散涂覆施用至所述纤维材料,或者作为浆状物、悬浮物、膜状物、网状物、无纺布或织物或喷射熔融物施用至所述纤维材料;随后,通过温度和/或压力的作用进行纤维结构体的固定。
32.如权利要求31所述的方法,其中,所述无纺布为固定无纺布。
33.制造权利要求1-30中任一项所述纤维-树脂复合材料的方法,其中,通过用由所述至少一种统计结构共聚酯制成的固定线加以缝合来进行所述纤维材料的固定和稳定。
34.权利要求1-30中任一项所述纤维-树脂复合材料在运动、休闲、机械工业、电子学、建筑业、医学工程、交通和运输工具、以及航空航天工程领域中的用途。
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CN104893069A (zh) * | 2015-06-09 | 2015-09-09 | 苏州德翔装饰工程有限公司 | 一种家具用聚乙烯木塑复合材料及其制备方法 |
EP3260436B1 (en) * | 2016-06-23 | 2019-12-18 | Evonik Operations GmbH | Reinforced building block made of autoclaved aerated concrete (aac) |
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EP3510004B1 (en) * | 2016-09-09 | 2021-11-24 | Prysmian S.p.A. | Optical fibre coated with a polyester coating |
CN108819378A (zh) * | 2018-06-28 | 2018-11-16 | 西安工程大学 | 一种利用牛仔布制备牛仔纤维增强复合材料的方法 |
BR112021003187A2 (pt) | 2018-08-21 | 2021-05-11 | Owens Corning Intellectual Capital, Llc | tecido de reforço multiaxial com um fio de costura para infusão de tecido melhorada |
CA3109485A1 (en) | 2018-08-21 | 2020-02-27 | Owens Corning Intellectual Capital, Llc | Hybrid reinforcement fabric |
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KR20130097658A (ko) | 2013-09-03 |
RU2622117C2 (ru) | 2017-06-13 |
US9346943B2 (en) | 2016-05-24 |
HUE026449T2 (en) | 2016-05-30 |
DK2631337T3 (en) | 2015-11-02 |
SI2631337T1 (sl) | 2015-12-31 |
SG193080A1 (en) | 2013-09-30 |
AU2013200689B2 (en) | 2016-03-03 |
MX345583B (es) | 2017-02-07 |
TW201341607A (zh) | 2013-10-16 |
EP2631337B1 (de) | 2015-09-23 |
ES2551587T3 (es) | 2015-11-20 |
JP6151037B2 (ja) | 2017-06-21 |
NZ606809A (en) | 2014-06-27 |
EP2631337A1 (de) | 2013-08-28 |
PL2631337T3 (pl) | 2015-12-31 |
US20160168783A1 (en) | 2016-06-16 |
CA2805922A1 (en) | 2013-08-24 |
TWI612189B (zh) | 2018-01-21 |
JP2013174037A (ja) | 2013-09-05 |
AU2013200689A1 (en) | 2013-09-12 |
CN103290687A (zh) | 2013-09-11 |
BR102013003950A2 (pt) | 2015-10-06 |
BR102013003950B1 (pt) | 2020-09-15 |
PT2631337E (pt) | 2015-11-17 |
RU2013106917A (ru) | 2014-08-20 |
KR102017502B1 (ko) | 2019-10-14 |
CL2013000505A1 (es) | 2013-07-26 |
MY172629A (en) | 2019-12-06 |
CA2805922C (en) | 2018-10-23 |
US20130225721A1 (en) | 2013-08-29 |
MX2013002018A (es) | 2013-09-03 |
AR090092A1 (es) | 2014-10-15 |
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