TW201918481A - 呋喃改質的化合物及寡聚物 - Google Patents
呋喃改質的化合物及寡聚物 Download PDFInfo
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Abstract
Description
本發明是關於一種化合物及寡聚物,特別是關於一種呋喃改質的化合物及寡聚物。
在2015年年底,歐盟發表了發表循環經濟指令(Circular Economy Package, CEP),未來的產品組成和零件需符合可修理(repaired)、耐久(durable)、易回收(recycled)等要件以達成循環經濟。此外,在2016年的巴黎協定中,提出減少溫室氣體排放以及把全球平均氣溫升高幅度控制在工業革命前水平以上低於2o
C之內。
目前在電子產品元件中,佔最大二氧化碳(CO2
)排放量的是印刷電路板(Printed Circuit Board, PCB),其排放量大於10萬kg CO2
/10000m2
PCB。因此,相關業者正面臨如何有效回收廢棄的印刷電路板來降低二氧化碳排放量並同時遵守能源相關產品生態設計指令(Ecodesign Directive)的挑戰。目前回收廢棄印刷電路板的做法是先將其碾碎,再對金屬和塑膠進行純化或掩埋處理。近年來隨著金屬純化技術的成熟,已可從一噸的印刷電路板提煉出130公斤的銅、19公斤的錫、和大約16盎司的金。然而,在印刷電路板中,還有大約佔了54.5%的塑膠,這是二氧化碳的主要排放來源。印刷電路板中的塑膠包括絕緣樹脂和玻璃纖維布,而目前用於印刷電路板的樹脂系統都是屬於熱固型聚合物,性質相當穩定,因此在回收方面便相當困難。雖然也有提出使用可分解的熱塑性高分子的做法,但仍需進一步地改善熱塑性高分子的玻璃轉移溫度、熱烈解溫度、和耐燃特性,才能達到與目前的印刷電路板絕緣樹脂相當的特性。
除了印刷電路板之外,應用在其他需在製程或使用上忍受高溫的產品中的樹脂組成物,在對於回收廢棄物之需求增加時,也面臨類似的挑戰。因此,存在著對類似樹脂組成物中的成分作進一步的調整以達成使其可維持在高溫的應用卻能被回收的目的。
根據本發明的實施例,本發明提供一種呋喃改質的化合物,其具有如下列化學式I所表示之結構: [化學式I]其中,x為1~5之整數,A為包含酮基、醯胺基、醯亞胺基、亞胺基、苯醚基或烯醇醚之基團,G為直接鍵、-O-、-N-、-Ar-NH-(CH2
)b
-、-Ar-O-(CH2
)b
-、-Ar-O-(CH2
)a
-NH-(CH2
)b
-、-(CH2
)a
-NH-(CH2
)b
-、-(CH2
)a
-O-(CH2
)b
-或-(CH2
)a
-CH(OH)-(CH2
)b
-NH-,Ar為具取代基或未取代的伸芳基,a係為1~5之整數,b為0~5之整數。
根據本發明的實施例,本發明提供一種呋喃改質的寡聚物,其具有如下列化學式II所表示之結構: [化學式II]其中,y為1~5之整數,B為包含胺、醯胺、馬來醯亞胺、酯基、苯醚或烯醇醚之重複基團,D為直接鍵、-O-、-N-、-Ar2
-NH-(CH2
)d
-、-Ar2
-O-(CH2
)d
-、-Ar2
-O-(CH2
)c
-NH-(CH2
)d
-、-(CH2
)c
-NH-(CH2
)d
-、-(CH2
)C
-O-(CH2
)d
-或-(CH2
)c
-CH(OH)-(CH2
)d
-NH-,Ar2
為具取代基或未取代的伸芳基,c係為1~5之整數,d為0~5之整數。。該呋喃改質的寡聚物的數量平均分子量為1000~12000。
為了對本發明之上述及其他方面有更佳的瞭解,下文特舉實施方案和實施例,並配合所附圖式詳細說明如下:
本發明的一實施例提供呋喃改質的化合物,其具有如下列化學式I所表示之結構: [化學式I]其中,x為1~5之整數,A為包含酮基、醯胺基、醯亞胺基、亞胺基、苯醚基烯醇醚之基團,G為直接鍵、-O-、-N-、-Ar-NH-(CH2
)b
-、-Ar-O-(CH2
)b
-、-Ar-O-(CH2
)a
-NH-(CH2
)b
-、-(CH2
)a
-NH-(CH2
)b
-、-(CH2
)a
-O-(CH2
)b
-或-(CH2
)a
-CH(OH)-(CH2
)b
-NH-,Ar為具取代基或未取代的伸芳基,a係為1~5之整數,b為0~5之整數。
具體地說,A可為、、、、、或,R為氫、鹵素、C1
~C8
烷基、C1
~C8
鹵烷基、C5
~C10
環烷基、或C6
~C12
芳香基,A以星號(*)所標示位置與G連接。更具體地說,R可為氫、氟、甲基、乙基、丙基、異丙基、正丁基、第二丁基、異丁基、叔丁基、戊基、己基、氟甲基、氟乙基、環戊基、環己基、苯基、聯苯基、或萘基。舉例來說,A可為或,A以星號(*)所標示位置與G連接,,其中R8
為CH3
或C2
H5
,t為1~5之整數,e為1~5之整數。
根據本揭露實施例,Ar可為具取代基或未取代之伸苯基(phenylene group)、聯苯伸基(biphenylene group)、伸萘基(naphthylene group)、伸噻吩基(thienylene group)、伸吲哚基(indolylene)、伸菲基(phenanthrenylene)、伸茚基(indenylene)、伸蒽基(anthracenylene)、或伸芴基(fluorenylene)。具體地說,Ar可為具1~4個C1
~C6
烷基取代基之伸苯基(phenylene group)、聯苯伸基(biphenylene group)、伸萘基(naphthylene group)、伸噻吩基(thienylene group)、伸吲哚基(indolylene)、伸菲基(phenanthrenylene)、伸茚基(indenylene)、伸蒽基(anthracenylene)、或伸芴基(fluorenylene)。
本發明的一實施例提供呋喃改質的寡聚物,其具有如下列化學式II所表示之結構: [化學式II]其中,y為1~5之整數,B為包含胺、醯胺、馬來醯亞胺、酯基或苯醚之重複基團,D為直接鍵、-O-、-N-、-Ar2
-NH-(CH2
)d
-、-Ar2
-O-(CH2
)d
-、-Ar2
-O-(CH2
)c
-NH-(CH2
)d
-、-(CH2
)c
-NH-(CH2
)d
-、-(CH2
)C
-O-(CH2
)d
-或-(CH2
)c
-CH(OH)-(CH2
)d
-NH-,Ar2
為具取代基或未取代的伸芳基,c係為1~5之整數,d為0~5之整數。該呋喃改質的寡聚物的數量平均分子量為1000~12000。
舉例來說,B可為、、、、、、、或,其中,B以星號(*)所標示位置與D連接,m為7~200的整數,n為7~200的整數,p、r及s為1~5的整數,q為5~50的整數,z為5~20的整數,R1
、R2
、R3
、R4
各自獨立地為C1
-C5
的烷基,T1
為直接鍵、C1
~C12
的直鏈或支鏈烷基、-O-、-S-或-NH-,Q為或,其中,R9
、R10
及R11
各自獨立地為CH3
或C2
H5
,T2
為C1
~C12
的直鏈或支鏈烷基,i、j及k為1~5的整數。
根據本揭露實施例,Ar2
可為具取代基或未取代之伸苯基(phenylene group)、聯苯伸基(biphenylene group)、伸萘基(naphthylene group)、伸噻吩基(thienylene group)、伸吲哚基(indolylene)、伸菲基(phenanthrenylene)、伸茚基(indenylene)、伸蒽基(anthracenylene)、或伸芴基(fluorenylene)。具體地說,Ar2
可為具1~4個C1
~C6
烷基取代基之伸苯基(phenylene group)、聯苯伸基(biphenylene group)、伸萘基(naphthylene group)、伸噻吩基(thienylene group)、伸吲哚基(indolylene)、伸菲基(phenanthrenylene)、伸茚基(indenylene)、伸蒽基(anthracenylene)、或伸芴基(fluorenylene)。
以下提供具體的實施例和比較例,以使得對於根據實施例之呋喃改質的化合物和/或寡聚物及其應用有更進一步的了解。在此,提出其在可逆交聯反應組成物及進而由該可逆交聯反應組成物形成之複合材料的材料為例。
[
呋喃改質的化合物和
/
或寡聚物的合成
]
[具有如化學式1-1所表示之結構的寡聚物] [化學式1-1]化學式1-1中的m為7~200、n為7~200,且由其表示之寡聚物的數量平均分子量為2000~12000。
實施例1
將60克的苯乙烯馬來酸酐(styrene maleic anhydride, SMA,購自Polyscope,重量平均分子量(Mw):7500)放入到80克的二甲基乙醯胺(DMAc,購自景明化工)溶劑中,進行預溶解。再加入29.6克的呋喃甲胺(furfurylamine, FA,購自ALDRICH),升溫至100o
C~160o
C,攪拌進行反應。待完全反應後,將溫度降至室溫,即可獲得具有如式(1-1)所表示之結構的寡聚物。接著,量測寡聚物各項物理特性,結果如表1所示。
實施例2
將60克的苯乙烯馬來酸酐(SMA,購自Polyscope,重量平均分子量(Mw):9000)放入到80克的二甲基乙醯胺(DMAc)溶劑中,進行預溶解。再加入22.33克的呋喃甲胺(FA,購自ALDRICH),升溫至100o
C~160o
C,攪拌進行反應。待完全反應後,將溫度降至室溫,即可獲得具有如式(1-1)所表示之結構的寡聚物。接著,量測寡聚物各項物理特性,結果如表1所示。
實施例3
將83克的苯乙烯馬來酸酐(SMA,購自Polyscope,重量平均分子量(Mw):10000)放入到115克的二甲基乙醯胺(DMAc)溶劑中,進行預溶解。再加入40克的呋喃甲胺(FA,購自ALDRICH),升溫至100o
C~160o
C,攪拌進行反應。待完全反應後,將溫度降至室溫,即可獲得具有如式(1-1)所表示之結構的寡聚物。接著,量測寡聚物各項物理特性,結果如表1所示。
[特性分析和結果]
使用反射式紅外線光譜分析儀(Spectrum One-54415,PERLIN ELMER)對實施例1~3製得的寡聚物進行IR光譜分析。所得之光譜資訊包括:1701 cm-1
和1776 cm-1
的-(CO)2
NH特徵峰,表示呋喃甲胺接枝上了苯乙烯馬來酸酐,形成了醯亞胺官能基;以及1006 cm-1
、1068 cm-1
的C-O-C特徵峰、和1491 cm-1
的C=C特徵峰,為呋喃甲胺上的呋喃官能基的訊號。此外,使用示差掃描熱分析儀(Q10,TA儀器股份有限公司)依照IPC-TM-650.2.4.24規範測量實施例1~3的寡聚物的玻璃轉移溫度(Tg),列於表1。並且使用凝膠透析層析儀(RI 830,JASCO)測量實施例1~3的寡聚物的重量平均分子量(Mw),列於表1。
表1
[具有如化學式1-2所表示之結構的寡聚物] [化學式1-2]化學式1-2中的x為5~47,且由其表示之寡聚物的數量平均分子量為1000~6000。
實施例4
將60克的聚苯醚(polyphenylene ether, PPE,購自Sabic,Mn:1600)放入到60克的二甲基乙醯胺(DMAc)溶劑中,進行預溶解。再加入6.9克的的呋喃甲胺(FA,購自ALDRICH),升溫至100o
C~160o
C,攪拌進行反應。待完全反應後,將溫度降至室溫,即可獲得具有如式(I-2)所表示之結構的寡聚物。接著,量測寡聚物各項物理特性,結果如表2所示。
實施例5
將60克的聚苯醚(PPE,購自Sabic,Mn:2350)放入到60克的二甲基乙醯胺(DMAc)溶劑中,進行預溶解。再加入8克的的呋喃甲胺(FA,購自ALDRICH),升溫至100o
C~160o
C,攪拌進行反應。待完全反應後,將溫度降至室溫,即可獲得具有如式(I-2)表示之結構的寡聚物。接著,量測寡聚物各項物理特性,結果如表2所示。
[特性分析和結果]
使用反射式紅外線光譜分析儀(Spectrum One-54415,PERLIN ELMER)對實施例4~5製得的寡聚物進行IR光譜分析。所得之光譜資訊包括:3200~3400 cm-1
的NH特徵峰,表示呋喃甲胺接枝上了聚苯醚;以及1006 cm-1
、1068 cm-1
的C-O-C特徵峰、和1491 cm-1
的C=C特徵峰,為呋喃甲胺上的呋喃官能基的訊號。此外,使用示差掃描熱分析儀(Q10,TA儀器股份有限公司)依照IPC-TM-650.2.4.24規範測量實施例4~5製得的寡聚物的玻璃轉移溫度(Tg),列於表2。並且使用凝膠透析層析儀(RI 830,JASCO)測量實施例4~5的寡聚物的重量平均分子量(Mw),列於表2。 表2
具有如式(I-3)所示結構之寡聚物
[具有如化學式1-3所表示之結構的寡聚物] [化學式1-3]化學式1-3中的z為5~20,且由其表示之寡聚物的數量平均分子量為900~3000。
實施例6
將50克的環氧樹脂壓克力寡聚物(DOUNLEMER1730,購自Double Bond chemical)放入到60克的二甲基乙醯胺(DMAc)溶劑中。再加入10克的的呋喃甲胺(FA,購自ALDRICH),升溫至100o
C~140o
C,攪拌進行反應。待完全反應後,將溫度降至室溫,即可獲得具有如式(I-3)所表示之結構的寡聚物。接著,量測寡聚物各項物理特性,結果如表3所示。
[特性分析和結果]
使用反射式紅外線光譜分析儀(Spectrum One-54415,PERLIN ELMER)對實施例6製得的寡聚物進行IR光譜分析。所得之光譜資訊包括:3200~3400 cm-1
的NH特徵峰,表示呋喃甲胺接枝上了聚苯醚;以及1006 cm-1
、1068 cm-1
的C-O-C特徵峰、和1491 cm-1
的C=C特徵峰,為呋喃甲胺上的呋喃官能基的訊號。此外,使用示差掃描熱分析儀(Q10,TA儀器股份有限公司)依照IPC-TM-650.2.4.24規範測量實施例4~5製得的寡聚物的玻璃轉移溫度(Tg),列於表3。並且使用凝膠透析層析儀(RI 830,JASCO)測量實施例6的寡聚物的重量平均分子量(Mw),列於表3。
表3
[具有如化學式1-4所表示之結構的化合物] [化學式1-4]化學式1-4中的T為-CH2
-CH(OH)-官能基或-CH2
-CH2
-官能基。
實施例7
將50克的三烯丙基異氰脲酸酯(triallyl isocyanurate, TAIC,購自ALDRICH)放入到60克的二甲基乙醯胺(DMAc)溶劑中。再加入19.48克的的呋喃甲胺(FA,購自ALDRICH),升溫至100o
C~160o
C,攪拌進行反應。待完全反應後,將溫度降至室溫,即可獲得具有如式(1-4)所示之結構的化合物。
實施例8
將50克的參(2,3-環氧丙基)異氰脲酸酯(tris (2,3-epoxy propyl) isocyanurate, TEPIC,購自Nissan Chemical)放入到60克的二甲基乙醯胺(DMAc)溶劑中。再加入23克的的呋喃甲胺(FA,購自ALDRICH),升溫至100o
C~160o
C,攪拌進行反應。待完全反應後,將溫度降至室溫,即可獲得具有如式(1-4)所示之結構的化合物。
特性分析和結果
使用反射式紅外線光譜分析儀(Spectrum One-54415,PERLIN ELMER)對實施例7~8製得的化合物進行IR光譜分析。所得之光譜資訊包括:3200~3400 cm-1
的NH特徵峰,表示呋喃甲胺接枝上了三烯丙基異氰脲酸酯或參(2,3-環氧丙基)異氰脲酸酯;以及1006 cm-1
、1068 cm-1
的C-O-C特徵峰、和1491 cm-1
的C=C特徵峰,為呋喃甲胺上的呋喃基的訊號。此外,使用示差掃描熱分析儀(Q10,TA儀器股份有限公司)依照IPC-TM-650.2.4.24規範測量實施例7~8製得的化合物的玻璃轉移溫度(Tg),列於表4。 表4
[可回收樹脂組成物的合成和分析]
[具有單一種類的呋喃改質的寡聚物的可回收樹脂組成物]
實施例9
取100.47克的在實施例1所合成的具有如式(1-1)所示之結構的寡聚物和50克的雙醯亞胺化合物BMI-1000(購自K.I. Chemical Industry,分子量:358.35),在50o
C~60o
C下反應30分鐘,形成膠水(可逆交聯反應組成物)。將膠水放置在烘箱中並在170o
C~190o
C進行反應,以得到組成物I。
實施例10
取271.2克的在實施例4所合成的具有如式(1-2)所示之結構的寡聚物和50克的BMI-1000(購自K.I. Chemical Industry),在50o
C~60o
C下反應30分鐘,形成膠水(可逆交聯反應組成物)。將膠水放置烘箱中並在170o
C~190o
C進行反應,以得到交聯組成物II。
實施例11
取40.18克的在實施例1所合成的具有如式(1-1)所示之結構的寡聚物和10克的BMI-1000(購自K.I. Chemical Industry),在50o
C~60o
C反應30分鐘,形成膠水(可逆交聯反應組成物)。將膠水放置烘箱中並在170o
C~190o
C進行反應,以得到交聯組成物III。
實施例12
取108.4克的在實施例4所合成的具有如式(1-2)所示之結構的寡聚物和10克的BMI-1000(購自K.I. Chemical Industry),在50o
C~60o
C反應30分鐘,形成膠水(可逆交聯反應組成物)。將膠水放置烘箱中並在170o
C~190o
C進行反應,以得到交聯組成物IV。
實施例13
取50.24克的在實施例1所合成的具有如式(1-1)所表示之結構的寡聚物和50克的BMI-1000(購自K.I. Chemical Industry),在50o
C~60o
C反應30分鐘,形成膠水(可逆交聯反應組成物)。將膠水放置烘箱中並在170o
C~190o
C進行反應,以得到交聯組成物V。
實施例14
取135.6克的在實施例4所合成的具有如式(1-2)所示之結構的寡聚物和50克的BMI-1000(購自K.I. Chemical Industry),在50o
C~60o
C反應30分鐘,形成膠水(可逆交聯反應組成物)。將膠水放置烘箱中並在170o
C~190o
C進行反應,以得到交聯組成物VI。
特性分析和結果
使用反射式紅外線光譜分析儀(Spectrum One-54415,PERLIN ELMER)對實施例9~14製得的交聯組成物I-VI進行IR光譜分析。所得之光譜資訊包括:原本在822 cm-1
的BMI-1000的特徵峰在反應後消失,且1068 cm-1
的呋喃官能基的C-O-C的特徵峰的訊號強度明顯下降,表示形成了交聯產物。此外,使用示差掃描熱分析儀(Q10,TA儀器股份有限公司)依照IPC-TM-650.2.4.24規範測量實施例9~14製得的組成物的玻璃轉移溫度(Tg),列於表5。並且使用示差掃描熱分析儀(Q10,TA儀器股份有限公司),取至少5 mg的樣品,以5o
C/min的速率升溫至350o
C,測量實施例9~17的組成物的可逆溫度(Tr),也列於表5。從表5列出的可逆溫度(Tr)可知,實施例的交聯組成物可穩定到160o
C以上的高溫,甚至可在260o
C的溫度都保持穩定。 表5
[具有複數種類的呋喃改質的化合物和/或寡聚物的組成物]
實施例15
取54.24克的在實施例1所合成的具有如式(1-1)所示之結構的寡聚物、135.6克的在實施例4所合成的具有如式(2-2)所示之結構的寡聚物、和50克的BMI-1000(購自K.I. Chemical Industry),在50o
C~60o
C下反應30分鐘,形成膠水(可逆交聯反應組成物)。將膠水放置烘箱中並在170o
C~190o
C進行反應,以得到交聯組成物VII。
實施例16
取54.24克的在實施例1所合成的具有如式(1-1)所示之結構的寡聚物、42.38克的在實施例7所合成的具有如式(1-4)所表示之結構的化合物、和50克的BMI-1000(購自K.I. Chemical Industry),在50o
C~60o
C下反應30分鐘,形成膠水(可逆交聯反應組成物)。將膠水放置烘箱中並在170o
C~190o
C進行反應,以得到交聯組成物VIII。
實施例17
取135.6克的在實施例4所合成的具有如式(1-2)所示之結構的寡聚物、42.38克的在實施例7所合成的具有如式(1-4)所示之結構的化合物、和50克的BMI-1000(購自K.I. Chemical Industry),在50o
C~60o
C下反應30分鐘,形成膠水(可逆交聯反應組成物)。將膠水放置烘箱中並在170o
C~190o
C進行反應,以得到交聯組成物IX。
實施例18
取33.5克的在實施例1所合成的具有如式(1-1)所示之結構的寡聚物、90.4克的在實施例4所合成的具有如式(1-2)所示之結構的寡聚物、28.3克的在實施例7所合成的具有如式(1-4)所示之結構的化合物、和50克的BMI-1000(購自K.I. Chemical Industry),在50o
C~60o
C下反應30分鐘,形成膠水(可逆交聯反應組成物)。將膠水放置在烘箱中並在170o
C~190o
C進行反應,以得到交聯組成物X。
[特性分析和結果]
使用反射式紅外線光譜分析儀(Spectrum One-54415,PERLIN ELMER)對實施例15~18製得的交聯組成物VII-X進行IR光譜分析。所得之光譜資訊包括:原本在822 cm-1
的BMI-1000的特徵峰在反應後消失,且1068 cm-1
的呋喃官能基上的C-O-C的特徵峰的訊號強度明顯下降,表示形成了交聯產物。此外,使用示差掃描熱分析儀(Q10,TA儀器股份有限公司)依照IPC-TM-650.2.4.24規範測量實施例15~18的組成物的玻璃轉移溫度(Tg),列於表6。並且使用示差掃描熱分析儀(Q10,TA儀器股份有限公司),取至少5 mg的樣品,以5o
C/min的速率升溫至350o
C,測量實施例18~21的交聯組成物的可逆溫度(Tr),也列於表6。從表6列出的可逆溫度(Tr)可知,實施例的組成物可穩定到160o
C以上的高溫,甚至可在300o
C的溫度都保持穩定。
表6
[可逆反應測試和結果]
將實施例9~18製得的交聯組成物粉碎。之後藉由提高溫度至大於300o
C的溫度使其斷鏈回到膠水狀態。將溫度降回60o
C~70o
C,其再度硬化變成塊材形狀。,使用反射式紅外線光譜分析儀(Spectrum One-54415,PERLIN ELMER)對該塊材進行IR光譜分析。所得之光譜資訊包括:822 cm-1
的BMI-1000上的C=C的特徵峰重新出現,且1068 cm-1
的呋喃官能基上的C-O-C的特徵峰的訊號強度明顯提高,表示交聯組成物發生斷鏈反應,回復成原本含呋喃基寡聚物和/或化合物、和BMI-1000的組成物。
[分析結果之討論]
對於根據實施例的可逆交聯反應組成物而言,雙醯亞胺化合物的二個醯亞胺官能基能夠分別和二個含呋喃基寡聚物或化合物的呋喃官能基發生1,2加成反應,而此立體結構在達到特定溫度時,由1,2加成反應形成的鍵結會斷鏈,使得含呋喃基寡聚物/化合物和雙醯亞胺化合物的橋接斷掉,回復成原本的反應物,從而有利於回收再利用。此外,根據實施例結果,本揭露可逆交聯反應組成物結構穩定,耐熱性高,且高可逆溫度有利於高溫製程的應用,舉例來說,應用在印刷電路板作為樹脂絕緣材料時,需在回焊製程中保持完好,因此可逆溫度最好大於等於250o
C者,這是因為前面的斷鏈溫度只有250-280。
[複合材料的合成和分析]
實施例19
取33.5克的在實施例1所合成的具有如式(1-1)所示之結構的寡聚物、90.4克的在實施例4所合成的具有如式(1-2)所示之結構的寡聚物、28.3克的在實施例7所合成的具有如化學式(1-4)所表示之結構的化合物、和50克的BMI-1000(購自K.I. Chemical Industry),再加入75克的二甲基乙醯胺(DMAc),在50o
C~60o
C下反應30分鐘,形成膠水。將膠水含浸在玻璃纖維布中,經過140o
C~170o
C的烘烤製成膠片(prepreg),再和銅箔壓合製成銅箔基板材。
[比較例]
取環氧樹脂828(BE-188,購自長春化工)為100 wt%、5phr的二氰二胺(dicyandiamide,購自景明化學)、和500 ppm的2-甲基咪唑(2-MI,購自景明化學),再加入丁酮(MEK,購自景明化學)溶劑,配製成固含量為70%的膠水。將膠水含浸在玻璃纖維布中,經過170o
C的烘烤製成膠片,再和銅箔壓合製成銅箔基板材。壓合條件為溫度170o
C~190o
C、反應1小時~2小時、壓力350 psi~450 psi。由此製成的銅箔基板材為一般用於印刷電路板的FR-4板材。
[特性分析和結果]
使用示差掃描熱分析儀(Q10,TA儀器股份有限公司)依照IPC-TM-650.2.4.24規範測量實施例19和比較例的銅箔基板材的玻璃轉移溫度(Tg),列於表7。使用熱機械分析儀(Q400,TA儀器股份有限公司)依照IPC-TMC-650.2.4.24規範測量實施例19和比較例的銅箔基板材的熱膨脹係數(CTE),列於表7。使用熱重分析儀(Q500,TA儀器股份有限公司)依照IPC-TM-650 2.3.40規範測量實施例19和比較例的銅箔基板材的裂解溫度(Td),列於表7。使用示差掃描熱分析儀(Q10,TA儀器股份有限公司),取至少5 mg的樣品,以5o
C/min的速率升溫至350o
C,測量實施例19和比較例的銅箔基板材的可逆溫度(Tr),列於表7。並且使用共振腔式微波介質儀(Resonant Cavity Type Microwave Dielectrometer,日本AET公司)依照JIS-compliant 1641規範測量實施例21和比較例的銅箔基板材在10 GHz的介電常數(Dk)和介電損失係數(Df),也列於表7。從表7可以看出,實施例19的銅箔基板材和比較例的銅箔基板材(亦即一般用於印刷電路板的FR-4板材)具有相近的介電常數和介電損失係數。但相較於比較例的銅箔基板材,實施例19的銅箔基板材具有可逆溫度300o
C,可藉由提高溫度到約300o
C來使得其中的樹脂逆反應成呋喃改質的化合物和/或寡聚物、和雙醯亞胺化合物,從而進行回收。 表7
[可逆反應測試和結果]
對實施例19的銅箔基板材進行蝕刻,除去銅箔。再把板材放入溫度約250~300o
C的溶液中,進行溶解和回收組成物。收集回收回來的樹脂組成物,使用反射式紅外線光譜分析儀(Spectrum One-54415,PERLIN ELMER)對其進行IR光譜分析。所得之光譜資訊包括:822 cm-1
的BMI-1000上的C=C的特徵峰重新出現,且1068 cm-1
的呋喃官能基上的C-O-C的特徵峰的訊號強度明顯提高,表示樹脂組成物發生斷鏈反應,回復成原本的含呋喃基寡聚物或化合物和BMI-1000。此外,回收回來的樹脂組成物在經過硬化後量測出來的玻璃轉移溫度和原本的樹脂組成物相同(實施例18),進一步佐證實施例19的複合材料可回收再利用。
[分析結果之討論]
由根據實施例之製造方法所製造而成的複合材料包括可逆交聯反應組成物,從而可提高複合材料的回收率。舉例來說,使用可逆溫度大於等於250o
C的組成物時,可改善印刷電路板的回收率,進而降低二氧化碳的排放量。此外,回收的組成物可重複使用,作為印刷電路板製程中的絕緣樹脂,或者作為次等原物料,而達成循環經濟。
綜上所述,雖然本發明已以實施方案和實施例揭露如上,然其並非用以限定本發明。本發明所屬技術領域中具有通常知識者,在不脫離本發明之精神和範圍內,當可作各種之更動與潤飾。因此,本發明之保護範圍當視後附之申請專利範圍所界定者為準。
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Claims (10)
- 一種呋喃改質的化合物,其具有如下列化學式I所表示之結構: [化學式I]其中,x為1~5之整數,A為包含酮基、醯胺基、醯亞胺基、亞胺基、苯醚基或烯醇醚之基團,G為直接鍵、-O-、-N-、-Ar-NH-(CH2 )b -、-Ar-O-(CH2 )b -、-Ar-O-(CH2 )a -NH-(CH2 )b -、-(CH2 )a -NH-(CH2 )b -、-(CH2 )a -O-(CH2 )b -或-(CH2 )a-CH(OH)-(CH2 )b -NH-,Ar為具取代基或未取代的伸芳基,a係為1~5之整數,b為0~5之整數。
- 如申請專利範圍第1項所述之呋喃改質的化合物,其中Ar為具取代基或未取代之伸苯基、聯苯伸基、伸萘基、伸噻吩基、伸吲哚基、伸菲基、伸茚基、伸蒽基、或伸芴基。
- 如申請專利範圍第1項所述之呋喃改質的化合物,其中Ar為具1~4個C1 ~C6 烷基取代基之伸苯基、聯苯伸基、伸萘基、伸噻吩基、伸吲哚基、伸菲基、伸茚基、伸蒽基、或伸芴基。
- 如申請專利範圍第1項所述之呋喃改質的化合物,其中A為、、、、、或,R為氫、鹵素、C1 ~C8 烷基、C1 ~C8 鹵烷基、C5 ~C10 環烷基、或C6 ~C12 芳香基,A以星號(*)所標示位置與G連接。
- 如申請專利範圍第4項所述之呋喃改質的化合物,其中R為氫、氟、甲基、乙基、丙基、異丙基、正丁基、第二丁基、異丁基、叔丁基、戊基、己基、氟甲基、氟乙基、環戊基、環己基、苯基、聯苯基、或萘基。
- 如申請專利範圍第1項所述之呋喃改質的化合物,其中A為或,A以星號(*)所標示位置與G連接,其中R8 為CH3 或C2 H5 ,t為1~5之整數,e為1~5之整數。
- 一種呋喃改質的寡聚物,其具有如下列化學式II所表示之結構: [化學式II]其中,y為1~3之整數,B為包含胺、醯胺、馬來醯亞胺、酯基或苯醚之重複基團,D為直接鍵、-O-、-N-、-Ar2 -NH-(CH2 )d -、-Ar2 -O-(CH2 )d -、-Ar2 -O-(CH2 )c -NH-(CH2 )d -、-(CH2 )c -NH-(CH2 )d -、-(CH2 )C -O-(CH2 )d -或-(CH2 )c -CH(OH)-(CH2 )d -NH-,Ar2 為具取代基或未取代的伸芳基,c係為1~5之整數,d為0~5之整數, 其中該呋喃改質的寡聚物的數量平均分子量為1000~12000。
- 如申請專利範圍第7項所述之呋喃改質的寡聚物,其中Ar2 為具取代基或未取代之伸苯基、聯苯伸基、伸萘基、伸噻吩基、伸吲哚基、伸菲基、伸茚基、伸蒽基、或伸芴基。
- 如申請專利範圍第7項所述之呋喃改質的寡聚物,其中Ar2 為具1~4個C1 ~C6 烷基取代基之伸苯基、聯苯伸基、伸萘基、伸噻吩基、伸吲哚基、伸菲基、伸茚基、伸蒽基、或伸芴基。
- 如申請專利範圍第7項所述之呋喃改質的寡聚物,其中B為、、、、、、、或,其中,B以星號(*)所標示位置與D連接,m為7~200的整數,n為7~200的整數,p、r及s為1~5的整數,q為5~50的整數,z為5~20的整數,R1 、R2 、R3 、R4 各自獨立地為C1 ~C5 的烷基,T1 為直接鍵、C1 ~C12 的直鏈或支鏈烷基、-O-、-S-或-NH-,Q為或,其中,R9 、R10 及R11 各自獨立地為CH3 或C2 H5 ,T2 為C1 ~C12 的直鏈或支鏈烷基,i、j及k為1~5的整數。
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