TW201434888A - 製備纖維強化複合材料之方法 - Google Patents
製備纖維強化複合材料之方法 Download PDFInfo
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- TW201434888A TW201434888A TW103103281A TW103103281A TW201434888A TW 201434888 A TW201434888 A TW 201434888A TW 103103281 A TW103103281 A TW 103103281A TW 103103281 A TW103103281 A TW 103103281A TW 201434888 A TW201434888 A TW 201434888A
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- resin
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- compound
- transition metal
- metal compound
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Abstract
本發明係關於製備纖維強化複合材料之方法,該方法包含接觸以下之步驟:(i)自由基可固化樹脂,(ii)以纖維總重量計總水含量為0.5-20重量%之纖維,(iii)至少一種選自錳、鐵及銅化合物之過渡金屬化合物,及(iv)過氧化物。
Description
本發明係關於一種製備纖維強化複合材料之方法及包含纖維之自由基可固化組合物。
基於聚合物之材料可經纖維強化以便增加剛性且阻止裂紋擴展。薄纖維可具有極高強度,且倘若其以機械方式良好地連接至基質,其可大大地改良組合物之整體特性。
存在兩個主要類別的纖維強化複合材料:短纖維強化材料及連續纖維強化材料。連續強化材料通常構成層化或層壓結構。編織及連續纖維型式通常以多種形式可供使用,經樹脂浸漬。
短纖維通常用於壓製成型及片材成型操作中。其形式有薄片、碎片或隨機配對物。常見的用於加強之纖維包括玻璃纖維、碳纖維、纖維素纖維(木纖維、紙纖維、稻草)、高強度聚合物(諸如芳族聚醯胺)及天然纖維。
通常於樹脂固化中應用氧化還原系統。習知氧化還原系統包含氧化劑(例如過氧化物)及可溶性過渡金屬離子作為促進劑。促進劑用於增大氧化劑在低溫下之活性,且因此加快固化速率。
典型促進劑系統包含過渡金屬鹽或錯合物。用於此目的之最常用之過渡金屬為鈷。
基於鈷之氧化還原系統於無水系統中運作極其良好。然而,一旦樹脂組合物含有大量水,固化即會受到不利影響,導致較長凝膠時
間及較低放熱峰。此意謂所有纖維必須在其用於製備纖維強化複合物之前完全乾燥。因此,吸引來自氛圍之水之纖維及含水(天然)之纖維必須在使用之前完全乾燥且甚至需要在乾燥氛圍下使用。
現已出人意料地發現基於Cu、Mn及/或Fe化合物之氧化還原系統在含水纖維存在下運作良好。此外,固化系統與含水纖維組合使用引起所得纖維強化複合材料之明顯改良的特性,例如與由乾燥纖維或乾燥的基於Co之系統製得之複合物相比強度增加、剛度減小及減震更佳。
本發明因此係關於一種製備複合材料之方法,該方法包含接觸以下之步驟:(i)自由基可固化樹脂,(ii)以纖維總重量計總水含量為5-20重量%之纖維,(iii)至少一種選自錳、鐵及銅化合物之過渡金屬化合物,及(iv)過氧化物。
本發明亦係關於一種自由基可固化組合物,其包含(i)自由基可固化樹脂,(ii)以纖維總重量計總水含量為0.5-20重量%之纖維,及(iii)至少一種選自錳、鐵及銅化合物之過渡金屬化合物。
本發明進一步關於一種兩組分組合物,其包含該自由基可固化組合物(組分A)及過氧化物(組分B)作為獨立組分,可混合該等獨立組分以引發固化。
適於根據本發明固化之樹脂包括醇酸樹脂、不飽和聚酯(UP)樹脂、乙烯基酯樹脂、(甲基)丙烯酸酯樹脂。較佳樹脂為(甲基)丙烯酸酯樹脂、UP樹脂及乙烯基酯樹脂。
自由基可固化樹脂可與其他類型樹脂(諸如環氧樹脂)組合。可用於本發明方法之較佳樹脂組合為UP樹脂及環氧樹脂之組合。
在本申請案之上下文中,術語「不飽和聚酯樹脂」及「UP樹脂」係指不飽和聚酯樹脂及烯系不飽和單體化合物之組合。術語「乙烯基酯樹脂」係指藉由環氧樹脂與不飽和單羧酸之酯化而製造且溶解
於烯系不飽和單體化合物(例如苯乙烯)中之樹脂。如上文所定義之UP樹脂及乙烯基酯樹脂為慣例且可購得的。
適於藉由本發明方法固化之UP樹脂為所謂鄰苯型樹脂、間苯型樹脂、間苯-新二醇型樹脂及二環戊二烯(DCPD)樹脂。該等樹脂之實例為順丁烯二酸型樹脂、反丁烯二酸型樹脂、烯丙基型樹脂、乙烯型樹脂及環氧型樹脂、雙酚A樹脂、對苯二甲酸樹脂及雜化樹脂。
本申請案中,不含其他烯系不飽和單體化合物(如苯乙烯)之丙烯酸酯及甲基丙烯酸脂樹脂稱為(甲基)丙烯酸酯樹脂。
適於存在於UP及乙烯基酯樹脂中之烯系不飽和單體之實例包括苯乙烯及苯乙烯衍生物,如α-甲基苯乙烯、乙烯基甲苯、茚、二乙烯基苯、乙烯基吡咯啶酮、乙烯基矽氧烷、乙烯基己內醯胺、芪、以及鄰苯二甲酸二烯丙酯、二苯亞甲基丙酮、烯丙基苯、甲基丙烯酸甲酯、丙烯酸甲酯、(甲基)丙烯酸、二丙烯酸酯、二甲基丙烯酸酯、丙烯醯胺、乙酸乙烯酯、三聚氰酸三烯丙酯、異氰尿酸三烯丙酯、用於光學應用之烯丙基化合物(諸如(二)乙二醇二烯丙基碳酸酯)、氯苯乙烯、第三丁基苯乙烯、丙烯酸第三丁酯、丁二醇二甲基丙烯酸酯、雙順丁烯二醯亞胺、雙檸康醯亞胺、雙衣康醯亞胺、單衣康醯亞胺、單檸康醯亞胺、含有官能基(例如另一不飽和官能基,例如正烯丙基檸康醯亞胺)之單檸康醯亞胺及其混合物。(甲基)丙烯酸酯反應性稀釋劑之適合實例為PEG200二(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、1,3-丁二醇二(甲基)丙烯酸酯、2,3-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯及其異構體、二乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、二(甲基)丙烯酸甘油酯、三羥甲基丙烷二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、二丙二醇二(甲基)丙烯酸酯、三丙二醇二(甲基)丙烯酸酯、PPG250二(甲基)丙烯酸酯、三環癸烷二羥甲基二(甲基)丙烯酸酯、1,10-癸二醇二(甲基)丙烯
酸酯、四乙二醇二(甲基)丙烯酸酯、三羥甲基丙烷三(甲基)丙烯酸酯、(甲基)丙烯酸縮水甘油酯及其混合物。
欲使用之烯系不飽和單體之量以樹脂之重量計較佳為至少0.1重量%,更佳為至少1重量%,且最佳為至少5重量%。烯系不飽和單體之量較佳不超過50重量%,更佳不超過40重量%,且最佳不超過35重量%。
引入複合材料之纖維充當強化物。適合之纖維之實例為玻璃纖維、耐綸纖維(nylon fibre)、聚酯纖維、芳族聚醯胺纖維(例如Twaron®)及天然纖維(例如黃麻、洋麻、工業大麻、亞麻(亞麻布)、苧麻、竹子等)。
該等纖維可含有上漿劑或另一添加劑以改良黏著性,諸如矽烷。
根據本發明使用之纖維之總水含量以濕纖維之總重量計為0.5-20重量%、較佳為2-20重量%、更佳為5-15重量%。纖維之水含量可藉由將纖維之樣品於熱風爐中於105℃下乾燥1小時且測定重量損失來測定。
纖維較佳根據本發明以樹脂之重量計以1-60重量%,更佳10-50重量%,甚至更佳15-40重量%,更佳20-40重量%且最佳20-30重量%之量使用。
適合之過渡金屬化合物之實例為鐵、銅或錳之鹽及錯合物,及該等化合物之組合。銅及鐵為最佳過渡金屬。甚至更佳為銅,以及銅及鐵之組合。
適合之錳、銅及鐵化合物為其鹵化物、硝酸鹽、硫酸鹽、磺酸鹽、磷酸鹽、膦酸鹽、氧化物、羧酸鹽以及此等金屬與配位體之錯合物。適合之羧酸鹽之實例為乳酸鹽、2-乙基己酸鹽、乙酸鹽、丙酸鹽、丁酸鹽、乙二酸鹽、月桂酸鹽、油酸鹽、亞油酸鹽、棕櫚酸鹽、
硬脂酸鹽、乙醯基丙酮酸鹽、辛酸鹽、壬酸鹽、庚酸鹽、新癸酸鹽或環烷酸鹽。配位體之實例為吡啶及WO 2011/83309中所揭示之三牙、四牙、五牙及六牙氮供體配位體。
較佳錳化合物為氯化錳、硝酸錳、硫酸錳、乳酸錳、2-乙基己酸錳、辛酸錳、壬酸錳、庚酸錳、新癸酸錳、環烷酸錳及乙酸錳,以及吡啶、卟啉基配位體之Mn錯合物,及WO 2011/83309中所揭示之三牙、四牙、五牙或六牙氮供體配位體之Mn錯合物。可使用Mn(II)、Mn(III)、Mn(IV)及Mn(VII)化合物中之任一者。
較佳銅化合物為氯化銅、硝酸銅、硫酸銅、乳酸銅、2-乙基己酸銅、辛酸銅、壬酸銅、庚酸銅、新癸酸銅、環烷酸銅及乙酸銅。Cu(I)及Cu(II)化合物均可使用。
較佳鐵化合物為氯化鐵、硝酸鐵、硫酸鐵、乳酸鐵、2-乙基己酸鐵、辛酸鐵、壬酸鐵、庚酸鐵、新癸酸鐵、環烷酸鐵、乙酸鐵,以及吡啶、卟啉基配位體之鐵錯合物,或WO 2011/83309之三牙、四牙、五牙或六牙氮供體配位體之鐵錯合物。Fe(II)及Fe(III)均可使用。其更佳為根據WO 2011/83309之三牙或五牙氮供體配位體之鐵(II)或鐵(III)錯合物。
對於Mn及Fe兩者,根據WO 2011/83309之較佳氮供體配位體為bispidon配位體及TACN-Nx配位體。較佳bispidon配位體為二甲基-2,4-二-(2-吡啶基)-3-甲基-7-(吡啶-2-基甲基)-3,7-二氮-雙環[3.3.1]壬-9-酮-1,5-二甲酸酯(N2py3o-Cl)。較佳的TACN-Nx配位體為1,4,7-三甲基-1,4,7-三氮環壬烷(Me3-TACN)。
欲用於本發明之方法及組合物之選自鐵、錳、銅及其混合物之過渡金屬的總量較佳為0.5-75毫莫耳/公斤樹脂,更佳為2-50毫莫耳/公斤,甚至更佳為2-25毫莫耳/公斤,且最佳為2-10莫耳/公斤樹脂。
除選自鐵、錳、銅及其組合之過渡金屬外,一或多種其他過渡
金屬化合物可存在於本發明之自由基可固化組合物中。適合之金屬之實例為鈷、鈦、釩、錫、鉻、鎳、鉬、鍺、鍶、鈀、鉑、鈮、銻、錸、鋨、銥、鉑、金、汞、碲、銣及/或鉍化合物。鈷化合物由於涉及該金屬之法規及毒性問題而為最不優選的。
在一較佳實施例中,本發明之方法不使用除鐵、錳及/或銅化合物之外的過渡金屬化合物。
在一較佳實施例中,鹼金屬或鹼土金屬化合物、含磷化合物及/或1,3-二酮可用於本發明之方法。
1,3-二酮之實例為乙醯基丙酮、苯甲醯基丙酮、及二苯甲醯基甲烷、及乙醯基乙酸酯(諸如二乙基乙醯基乙醯胺)、二甲基乙醯基乙醯胺、二丙基乙醯基乙醯胺、二丁基乙醯基乙醯胺、乙醯基乙酸甲酯、乙醯基乙酸乙酯、乙醯基乙酸丙酯及乙醯基乙酸丁酯。
鹼金屬或鹼土金屬化合物之實例為鹼金屬或鹼土金屬羧酸鹽,諸如鹼金屬及鹼土金屬之2-乙基己酸鹽、辛酸鹽、壬酸鹽、庚酸鹽、新癸酸鹽及環烷酸鹽。較佳鹼金屬為K。
含磷化合物之實例為具有式P(R)3及P(R)3=O之含磷化合物,其中各R獨立地選自氫、具有1至10個碳原子之烷基及具有1至10個碳原子之烷氧基。較佳地,至少兩個R基團係選自烷基或烷氧基。適合含磷化合物之特定實例為磷酸二乙酯、磷酸二丁酯、磷酸三丁酯、磷酸三乙酯(TEP)、亞磷酸二丁酯及磷酸三乙酯。
乙醯基乙酸酯為尤其較佳的促進劑。尤其較佳為二乙基乙醯基乙醯胺。甚至更佳為二乙基乙醯基乙醯胺與2-乙基己酸鉀之組合。亦較佳為二乙基乙醯基乙醯胺與磷酸二丁酯之組合。
自由基可固化組合物可進一步含有含氮鹼,諸如三級胺,如三乙胺、二甲基苯胺、二乙基苯胺或N,N-二甲基-對甲苯胺(DMPT);多元胺,如1,2-(二甲基胺)乙烷;二級胺,如二乙胺;乙氧基化胺,如
三乙醇胺、二甲胺基乙醇、二乙醇胺(DETA)或單乙醇胺;及芳族胺,如聯吡啶。
含氮鹼較佳以0.5-10公克/公斤樹脂之量使用。
可存在於本發明之自由基可固化組合物中之視情況選用之添加劑為填充劑、顏料、抑制劑及促進劑。
在一較佳實施例中,自由基可固化組合物包含填充劑。填充劑之實例為石英、砂、氫氧化鋁、氫氧化鎂、白堊、氫氧化鈣、黏土及石灰。
可能需要具有存在於自由基可固化組合物中之還原劑。還原劑之實例為抗壞血酸、甲醛次硫酸鈉(SFS)、還原糖(如葡萄糖及果糖)、草酸、膦、亞磷酸鹽、有機或無機亞硝酸鹽、有機或無機亞硫酸鹽、有機或無機硫化物、硫醇及醛,及其混合物。抗壞血酸為較佳還原劑,在本說明書中,該術語包括L-抗壞血酸及D-異抗壞血酸。
可以不同方法向自由基可固化樹脂中添加過渡金屬化合物及一或多種其他化合物。一種方法涉及向樹脂中添加個別化合物,隨後添加過氧化物。此舉可在臨添加過氧化物之前進行或在此之前幾天或幾週進行。在後一種情況下,吾人提及預促進樹脂組合物,其包含樹脂及促進劑成分且可儲存直至進一步與過氧化物一起使用且固化。
另一方法涉及預製備含有過渡金屬化合物及視情況選用之一或多種上文提及之其他化合物的溶液,該溶液可儲存直至進一步使用且添加至樹脂中(稱作「促進劑溶液」)。
預促進樹脂可藉由將促進劑系統之個別成分添加至樹脂中或藉由添加此等成分呈促進劑溶液形式之混雜物來製備。
適用於本發明方法之促進劑溶液除過渡金屬化合物及上文提及之視情況選用之其他化合物外還可包含一或多種溶劑。
適合溶劑之實例包括脂族烴溶劑、芳族烴溶劑以及攜有醛、
酮、醚、酯、醇、磷酸酯或羧酸基團之溶劑。適合溶劑之實例為脂族烴溶劑,諸如白色石油腦及無味礦油精(OMS);芳族烴溶劑,諸如環烷烴及環烷烴與石蠟之混合物;異丁醇;戊醇;1,2-二肟;N-甲基吡咯啶酮;N-乙基吡咯啶酮;二甲基甲醯胺(DMF);二甲亞碸(DMSO);2,2,4-三甲基戊二醇二異丁酸酯(TxIB);酯,諸如順丁烯二酸二丁酯、丁二酸二丁酯、乙酸乙酯、乙酸丁酯、酮戊二酸單酯及酮戊二酸二酯、丙酮酸酯、及抗壞血酸酯(諸如抗壞血酸棕櫚酸酯);醛;單酯及二酯,更特定言之丙二酸二乙酯及丁二酸二乙酯;1,2-二酮,特定言之雙乙醯及乙二醛;苯甲醇及脂肪醇。
尤其所需之溶劑類型為羥基官能性溶劑,其包括式HO-(-CH2-C(R1)2-(CH2)m-O-)n-R2之化合物,其中各R1獨立地選自由以下組成之群:氫、具有1-10個碳原子之烷基及具有1至10個碳原子之羥基烷基,n=1-10,m=0或1,且R2為氫或具有1-10個碳原子之烷基。各R1最佳獨立地選自H、CH3及CH2OH。適合羥基官能性溶劑之實例為二醇類,如二乙二醇單丁基醚、乙二醇、二乙二醇、二丙二醇及聚乙二醇、甘油及季戊四醇。
促進劑溶液可藉由簡單地混合成分,視情況伴以中間加熱及/或混合步驟來製備。
若促進劑溶液在本發明方法中用於將過渡金屬添加至樹脂中,則促進劑溶液通常以樹脂之重量計以至少0.01重量%,較佳至少0.1重量%,且較佳不超過5重量%,更佳不超過3重量%促進劑溶液之量使用。
適用於本發明方法且適合存在於兩組分組合物之組分B中之過氧化物包括無機過氧化物及有機過氧化物,諸如習知使用之酮過氧化物、過氧化酯、二芳基過氧化物、二烷基過氧化物及過氧二碳酸酯以及過氧碳酸酯、過氧縮酮、氫過氧化物、二醯基過氧化物及過氧化
氫。較佳過氧化物為有機氫過氧化物、酮過氧化物、過氧化酯及過氧碳酸酯。尤其較佳過氧化物為甲基乙基酮過氧化物及甲基異丙基酮過氧化物。
習此相關技藝之人士將理解過氧化物可與習知添加劑(例如填充劑、顏料及減敏劑)組合。減敏劑之實例為親水性酯及烴溶劑。欲用於固化樹脂之過氧化物之量較佳為至少0.1重量份/百份樹脂(phr),更佳為至少0.5phr,且最佳為至少1phr。過氧化物之量較佳不超過8phr,更佳不超過5phr,最佳不超過2phr。
為了固化自由基可固化樹脂,將過氧化物添加至樹脂、纖維及過渡金屬化合物之混合物中,且混合並分散所得混合物。視引發劑系統、促進劑系統、調適固化速率之化合物及待固化之樹脂組合物而定,固化製程可在-15℃至250℃之任何溫度下進行。其較佳在常用於諸如以下之應用之環境溫度下進行:手工塗佈(hand lay-up)、噴佈、絲捲繞、樹脂傳遞模塑、真空注入或浸漬、塗佈(例如凝膠塗佈及標準塗佈)、按鈕製造、離心澆鑄、波紋板或平面板、換襯系統、廚房水槽通孔澆鑄化合物等。然而,其亦可用於SMC、BMC、拉擠技術及其類似技術中,對於該等技術使用至多180℃,更佳至多150℃,最佳至多100℃之溫度。
可對固化複合材料進行後固化處理以進一步使硬度最佳化。該後固化處理通常在40℃至180℃範圍內之溫度下進行30分鐘至15小時。
固化組合物可用於各種應用中,包括海事應用、化學錨定、加屋面、建築、換襯、管道及槽、鋪地、風車葉片、層合物、汽車部件汽車、卡車、火車、飛機等。
下列材料用於以下實例:
Synolite 1967-X1 - 非預促進DCPD聚酯樹脂(購自DSM)
Butanox® M50 - 活性氧含量為8.9重量%之甲基乙基酮過氧化物(50重量%於鄰苯二甲酸二甲酯中;購自AkzoNobel)
NouryactTM CF32 - 基於鐵之促進劑溶液,購自AkzoNobel
促進劑NL49-P - 2-乙基己酸鈷(II),1%Co於溶劑混合物中(購自AkzoNobel)
抑制劑NLD-20 - 基於2,6-二第三丁基-4-甲苯酚之抑制劑,購自AkzoNobel
『原樣』無紡亞麻 - 在13.9℃溫度下在71%相對濕度下儲存後,含有約9.3重量%水之「非預處理」亞麻
乾燥無紡亞麻 - 在105℃下於鹵素/熱空氣乾燥器中乾燥1小時之亞麻,與「原樣」亞麻相比,引起9.3重量%之重量損失
濕無紡亞麻 - 在20℃及100%RH下在封閉式容器中儲存96小時後,含有約14重量%水之經水蒸氣飽和之亞麻
使用30×50×0.4cm之封閉式真空注入模具製備測試面板。在模具中放入兩片厚度為5mm之無紡亞麻。樹脂組合物藉由以下方式製備:混合100重量份(pbw)樹脂、1pbw促進劑溶液、1pbw過氧化物及0.5pbw抑制劑NLD-20,將混合物注入模具中,且使混合物固化。凝膠時間為約45分鐘。在固化期間使模具保持在20℃。成品組合物中,所得纖維含量為約35重量%。
含有基於Co之促進劑及濕亞麻(具有14重量%之水含量)之固化板含有潤濕不良部分,而含有基於Fe之促進劑之固化板及含有基於Co之促進劑與乾燥亞麻之組合的板看起來很好。
自測試面板取出測試條帶,且根據ISO 527於Instron 3367儀器上量測撕裂強度、斷裂伸長率及楊氏模數(Young's modulus)。
Xa意謂:不完全固化
此等資料顯示,與使用乾燥亞麻所獲得之面板(經Co或Fe促進)相比,含有含鐵促進劑及濕亞麻之固化面板具有更高的撕裂強度,尤其在縱向上。
此樣品之斷裂伸長率亦比其他樣品更高,而剛度(楊氏模數)更小。
Claims (15)
- 一種製備纖維強化複合材料之方法,該方法包含接觸以下之步驟:(i)自由基可固化樹脂,(ii)以纖維總重量計總水含量為0.5-20重量%之纖維,(iii)至少一種選自錳、鐵及銅化合物之過渡金屬化合物,及(iv)過氧化物。
- 如請求項1之方法,其中該等纖維為選自亞麻、黃麻、洋麻、工業大麻、竹子及苧麻之天然纖維。
- 如請求項1或2之方法,其中該樹脂為不飽和聚酯樹脂、乙烯基酯樹脂、(甲基)丙烯酸酯樹脂。
- 如請求項1或2之方法,其中該過渡金屬化合物為銅化合物、鐵化合物或其組合。
- 如請求項1或2之方法,其中該過氧化物係選自由以下組成之群:有機氫過氧化物、酮過氧化物、過氧碳酸酯及過氧化酯。
- 如請求項5之方法,其中該過氧化物為酮過氧化物。
- 如請求項1或2之方法,其中該自由基可固化樹脂組合物係藉由將該過渡金屬化合物添加至呈溶液形式之該樹脂中而製備,除該過渡金屬化合物之外,其還包含鹼金屬或鹼土金屬化合物、含磷化合物及/或1,3-二酮。
- 如請求項1或2之方法,其中該過渡金屬化合物係以1-75毫莫耳/公斤樹脂之量添加至該樹脂中。
- 一種自由基可固化組合物,其包含(i)自由基可固化樹脂、(ii)以纖維總重量計總水含量為0.5-20重量%之纖維及(iii)至少一種選自錳、鐵及銅化合物之過渡金屬化合物。
- 如請求項9之自由基可固化組合物,其中該樹脂為不飽和聚酯樹脂、乙烯基酯樹脂或(甲基)丙烯酸酯樹脂。
- 如請求項9或10之自由基可固化組合物,其中該過渡金屬化合物為銅化合物、鐵化合物或其混合物。
- 如請求項9或10之自由基可固化組合物,其另外包含鹼金屬或鹼土金屬化合物、含磷化合物及/或1,3-二酮。
- 一種兩組分組合物,其包含組分A及B;組分A包含如請求項9至12中任一項之自由基可固化組合物,且組分B包含過氧化物。
- 如請求項13之兩組分組合物,其中該過氧化物係選自由以下組成之群:有機氫過氧化物、酮過氧化物、過氧碳酸酯及過氧化酯。
- 如請求項14之兩組分組合物,其中該過氧化物為酮過氧化物。
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US4487797A (en) | 1983-12-01 | 1984-12-11 | Ppg Industries, Inc. | Glass fibers to reinforce polymeric materials |
FR2603521B1 (fr) * | 1986-09-04 | 1989-01-13 | Du Pin Cellulose | Materiaux composites a base d'une matrice de resine polyester renforcee par des fibres cellulosiques discontinues et procede de fabrication |
US5830395A (en) * | 1997-08-12 | 1998-11-03 | E. I. Du Pont De Nemours And Company | Process for making a uniform dispersion of aramid fibers and polymer |
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EP2951233B1 (en) | 2016-12-14 |
US9873795B2 (en) | 2018-01-23 |
KR20150114466A (ko) | 2015-10-12 |
AR094669A1 (es) | 2015-08-19 |
US20150322264A1 (en) | 2015-11-12 |
RU2653695C2 (ru) | 2018-05-14 |
MX2015009462A (es) | 2015-09-24 |
JP2016504477A (ja) | 2016-02-12 |
ES2616904T3 (es) | 2017-06-14 |
AU2014211548B2 (en) | 2017-02-23 |
AU2014211548A1 (en) | 2015-07-02 |
SI2951233T1 (sl) | 2017-04-26 |
DK2951233T3 (en) | 2017-03-13 |
CN104955881B (zh) | 2018-04-06 |
CN104955881A (zh) | 2015-09-30 |
EP2951233A1 (en) | 2015-12-09 |
JP6082823B2 (ja) | 2017-02-15 |
IL239473A0 (en) | 2015-07-30 |
CA2894825A1 (en) | 2014-08-07 |
PL2951233T3 (pl) | 2017-08-31 |
TWI613235B (zh) | 2018-02-01 |
ZA201504651B (en) | 2016-07-27 |
PH12015501553A1 (en) | 2015-09-21 |
IL239473A (en) | 2017-05-29 |
BR112015016781A2 (pt) | 2017-07-11 |
RU2015135572A (ru) | 2017-03-07 |
MY173381A (en) | 2020-01-21 |
PH12015501553B1 (en) | 2015-09-21 |
WO2014118101A1 (en) | 2014-08-07 |
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