TWI417311B - 熱硬化性樹脂組成物及其用途 - Google Patents
熱硬化性樹脂組成物及其用途 Download PDFInfo
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- TWI417311B TWI417311B TW95138352A TW95138352A TWI417311B TW I417311 B TWI417311 B TW I417311B TW 95138352 A TW95138352 A TW 95138352A TW 95138352 A TW95138352 A TW 95138352A TW I417311 B TWI417311 B TW I417311B
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- epoxy resin
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Description
本發明乃不含由鹵素系難燃劑或銻化合物而能提供具有優異之難燃性及耐熱性之硬化物,且為膜狀(或薄膜狀)的硬化物時,具有充分之柔軟性(flexibility),同時,具有優異之貯藏安定性之熱硬化性樹脂組成物有關。
環氧樹脂藉由種種硬化劑硬化時,通常可成為機械特性、耐水性、耐藥性、耐熱性、電特性等優異之硬化物,因此,可利用在黏接劑、塗料、層積板、成型材料、注型材料等廣泛領域中。以往,最常用之環氧樹脂例如雙酚A型環氧樹脂。該環氧樹脂之硬化物本身缺少難燃性,以往為了賦與難燃性,藉由於環氧樹脂調配難燃劑等而達成。該難燃劑,一般使用溴化物或難燃佐劑之銻化合物等,周知例舉有四溴化雙酚A及其環氧化物,四溴化雙酚A以雙酚A型環氧樹脂反應而成之化合物等。又,環氧樹脂之硬化劑,周知者例如酸酐或胺系化合物。在電/電子領域中,就耐熱性等之可信性而言,以使用酚/酚醛清漆為多。最近,以改善耐熱性、柔軟性為目的,也有使用具有酚性羥基之芳族聚醯亞胺為硬化劑之例(參照專利文獻1)。
另一方面,聚醯亞胺具備優異之耐熱性、難燃性、柔軟性、機械特性、電特性及耐藥性,因此,廣泛地使用在電/電子零件、半導體、通訊器材及其電路零件、周邊機器等。聚醯亞胺樹脂由於難溶於有機溶劑,所以將其前驅物之聚醯胺酸塗布於基材,其次有加熱,脫水之需要。此時產生之硬化收縮所造成彎曲或生成水成為問題。最近,研發有溶劑可溶性聚醯亞胺,並使用在塗布用途,配向膜,絕緣膜等(參照專利文獻2)。
專利文獻1:日本特開2005-29720號公報。
專利文獻2:日本PCT專利WO2003-060010號公報。
然而,上述含溴化合物,雖然其難燃性優異,廢棄或焚燒時可能會產生成為環境污染原因之物質,此點會成為問題而受指責。另外,做為難燃佐劑使用之銻化合物也有毒性之顧慮。
又,使用酚醛清漆為硬化劑所得環氧樹脂之硬化物,雖然其信賴性優異,但該硬化物剛直而缺少柔軟性(flexibility)。以提升耐熱性、柔軟性為目的,尚有將具有酚性羥基之芳族聚醯胺做為硬化劑使用之環氧樹脂,該樹脂之柔軟性,雖得顯著提升,但耐熱性不足,再加以硬化膜之彈性率低,膜特性不足。
本發明之目的在提供可對應於現代各種電子機器之高機能化,能賦予具有優異之難燃性、耐熱性、機械特性、柔軟性等諸特性之硬化物之樹脂組成物及其硬化物。
本發明研究者為解決上述課題,致力研究結果終於完成了本發明。
即,本發明由下列各項所構成:(1)含有酚性羥基之聚醯亞胺樹脂(A)及環氧樹脂(B),該聚醯亞胺樹脂(A)之含有比率相對於環氧樹脂(B)中之環氧基1當量計,該聚醯亞胺樹脂(A)中之活性氫當量為0.7至1.2當量之比率為其特徵之熱硬化性樹脂組成物。
(2)如上述(1)項之熱硬化性樹脂組成物,其中,具酚性羥基之聚醯亞胺樹脂(A)係由具酚性羥基之二胺成分(以下簡稱為胺基酚類(a)),不具酚性羥基之二胺成分(下文中簡稱為二胺化合物(b))及四元酸二酐(c)所製造而成。
(3)如上述(2)項之熱硬化性樹脂組成物,其中,胺基酚類(a)包括由3,3’-二胺基-4,4’-二羥基二苯基碸、3,3’-二胺基-4,4’-二羥基二苯基醚、3,3’-二胺基-4,4’-二羥基聯苯、3,3’-二羥基-4,4’-二胺基聯苯、2,2-雙(3-胺基-4-羥苯基)丙烷、1,3-六氟-2,2-雙(3-胺基-4-羥苯基)丙烷及9,9’-雙(3-胺基-4-羥苯基)芴所成組群中選擇1種以上者。
(4)如上述(1)或(2)項之熱硬化性樹脂組成物,其中,聚醯亞胺樹脂(A)係在其架構中具有磺醯基。
(5)如上述(1)至(4)項中任一項之熱硬化性樹脂組成物,其中,環氧樹脂(B)包括由酚醛清漆型環氧樹脂、含有伸二甲苯架構酚/酚醛清漆型環氧樹脂,含有聯苯架構酚醛清漆型環氧樹脂、雙酚A型環氧樹脂、雙酚F型環氧樹脂、四甲基聯苯酚型環氧樹脂、三苯基甲烷型環氧樹脂及乙二醛型環氧樹脂所成組群中選擇1種以上者。
(6)如上述(1)至(5)項中任一項之熱硬化性樹脂組成物,其中,含有硬化促進劑。
(7)含有如上述(1)至(6)項中任一項之熱硬化性樹脂組成物及溶劑之清漆。
(8)在平面狀支持體之雙面或片面具有如上述(1)至(6)項中任一項之組成物所構成層之片狀物。
(9)如上述(8)項之片狀物,其中,平面狀支持體係聚醯亞胺膜、金屬箔或剝離膜。
(10)一種預浸物(prepreg),含浸上述(7)項之清漆於基材,經乾燥而得者。
(11)一種硬化物,上述(1)至(6)項中任一項之熱硬化性樹脂組成物經硬化而得。
(12)一種熱硬化性樹脂組成物,其特徵為含有酚性羥基之聚醯亞胺樹脂(A)及環氧樹脂(B),該具有酚性羥基之聚醯亞樹脂(A)係由胺基酚類(a)、二胺基化合物(b)及四元酸二酐(c)所製造者,而該二胺基化合物(b)係由間苯二胺、對苯二胺、間甲苯二胺、4,4’-二胺基二苯基醚、3,3’-二甲基-4,4’-二胺基二苯基醚、3,4’-二胺基二苯基醚、4,4’-二胺基二苯基硫醚、3,3’-二甲基-4,4’-二胺基二苯基硫醚、3,3’-二乙氧基-4,4’-二胺基二苯基硫醚、3,3’-二胺基二苯基硫醚、4,4’-二胺基二苯甲酮、3,3’-二甲基-4,4’-二胺基二苯甲酮、3,3’-二胺基二苯基甲烷、4,4’-二胺基二苯基甲烷、3,4’-二胺基二苯基甲烷、3,3’-二甲氧基-4,4’-二胺基二苯基硫醚、2,2’-雙(3-胺基苯基)丙烷、2,2’-雙(4-胺基苯基)丙烷、4,4’-二胺基二苯基亞碸、3,3’-二胺基二苯基碸、4,4’-二胺基二苯基碸、聯苯胺、3,3’-二甲基聯苯胺、3,3’-二甲氧基聯苯胺、3,3’-二胺基聯苯、對二甲苯二胺、間二甲苯二胺、鄰二甲苯二胺、2,2’-雙(3-胺基苯氧基苯基)丙烷、2,2’-雙(4-胺基苯氧基苯基)丙烷、1,3-雙(4-胺基苯氧基苯基)苯、1,3’-雙(3-胺基苯氧基苯基)丙烷、雙(4-胺基-3-甲基苯基)甲烷、雙(4-胺基-3,5-二甲基苯基)甲烷、雙(4-胺基-3-乙基苯基)甲烷、雙(4-胺基-3,5-二乙基苯基)甲烷、雙(4-胺基-3-丙基苯基)甲烷、雙(4-胺基-3,5-二丙基苯基)甲烷、聚矽氧二胺、異佛爾酮二胺、己二胺、或三甲基己二胺所成組群中選擇一種或二種以上者。
(13)如上述(3)項之熱硬化性樹脂組成物,其中,對於100重量份之該聚醯亞胺樹脂(A)含有30至100重量份之環氧樹脂(B)。
(14)如上述(2)項之熱硬化性樹脂組成物,其中,含有酚性羥基之聚醯亞胺樹脂(A)及環氧樹脂(B),該具有酚性羥基之聚醯亞胺樹脂(A)係由胺基酚類(a),二胺基化合物(b)及四元酸二酐(c)所製造者,該胺基酚類(a)係由胺基及羥基二者所取代之兩個苯基經由-SO2
-、-O-或-(可經氟取代之CH3
)C(可經氟取代之CH3
)-所結合之二胺基二羥基二苯基化合物;二胺基化合物(b)係具有胺基取代基之苯基(苯環可經C1至C4烷基或C1至C4烷氧基取代)2個直接或經由交聯基結合而成之二胺基二苯基化合物者。
(15)如上述(1)項之熱硬化性樹脂組成物,其中,該具有酚性羥基之聚醯亞胺(A)係由3,3’,4,4’-二苯基碸四羧酸二酐及3,3’-二胺基-4,4’-二羥基二苯基醚及4,4’-二胺基二苯基醚之縮聚合,或3,3’,4,4’-聯苯四羧酸二酐及3,3’-二胺基-4,4’-二羥基二苯基碸及異佛爾酮二胺間之縮聚合而得者。
(16)如上述(14)項之熱硬化性樹脂組成物,其中,二胺基化合物(b)之交聯基係-O-、-O-C6
H4
-O-、-SO2
-或可具有歧鏈之C1至C10伸烷基。
(17)如上述(14)項之熱硬化性樹脂組成物,其中,二胺基化合物(b)包括由4,4’-二胺基二苯基醚、1,3-雙(3-胺基苯氧基)苯及異佛爾酮二胺所成組群中選擇至少一種。
本發明之熱硬化性樹脂組成物之硬化物,其難燃性、耐熱性、機械特性、柔軟性皆優異,又,該樹脂組成物,特別是清漆之貯存安定性優異,所以有用於提供成形材料、注型材料、層積材料、塗料、被覆層等之廣泛用途。
本發明之熱硬化性樹脂組成物含有具酚性羥基之聚醯亞胺樹脂(A)及環氧樹脂(B)。該具酚性羥基之聚醯亞胺樹脂(下文中或簡稱為聚醯亞胺樹脂(A)),祇要是具有酚性羥基之聚醯亞胺別無限制。該聚醯亞胺樹脂通常由二胺成分及四元酸二酐縮合而得。該二胺成分及四元酸二酐可藉使用至少一方為具有酚性羥基之化合物而得上述之聚醯亞胺(A)。又,該二胺成分及該四元酸二酐之至少一方為具有磺醯基之化合物時,可得較佳之聚醯亞胺(A)。
本發明中,以使用具有酚性羥基之二胺成分所製得聚醯亞胺(A)為佳。又,本發明中,該具有酚性羥基之二胺成分(下文中,或稱為胺基酚類(a))和不具有酚性羥基之二胺成分(下文中,方便上簡稱為二胺基化合物(b)。因此,此處所謂二胺基化合物(b)指(a)成分以外之二胺成分)可組合使用,該二胺成分和四元酸二酐(c)縮合而成樹脂為最佳。
本發明之製造具有酚性羥基之聚醯亞胺樹脂(A)所用胺基酚類(a)之羥基當量為110至900g/當量為佳,其中,以120至500g/當量為較佳。羥基當量未達110之化合物不容易獲得,當羥基當量超過900時,羥基之導入率降低、交聯密度降低、各種特性也有降低之虞。
該胺基酚類(a),祇要一分子中至少具有兩個胺基及一個酚性羥基之化合物就別無限制。可使用之胺基酚類(a),例如3,3’-二胺基-4,4’-二羥基二苯基碸、3,3’-二胺基-4,4’-二羥基二苯基醚、3,3’-二胺基-4,4’二羥基聯苯、3,3’-二羥基-4,4’-二胺基聯苯、2,2-雙(3-胺基-4-羥基苯基)丙烷、1,3-六氟-2,2-雙(3-胺基-4-羥基苯基)丙烷、9,9’-雙(3-胺基-4-羥基苯基)芴等,然而不侷限於上述範圍。上述可使用1種或2種以上混合使用。
較佳之例如3,3’-二胺基-4,4’-二羥基二苯基碸、3,3’-二胺基-4,4’-二羥基二苯基醚、2,2-雙(3-胺基-4-羥基苯基)丙烷等之以胺基及羥基之兩者所取代之兩個苯基、藉由例如-SO2
-、-O-或-(可經氟取代之CH3
)C(可經氟取代之CH3
)-等所結合而成之二胺基二羥基二苯基化合物,更佳之例如3,3’-二胺基-4,4’-二羥基二苯基碸或3,3’-二胺基-4,4’-二羥基二苯基醚等之以胺基及羥基之兩者所取代之兩個苯基,藉由例如-SO2
-或-O-結合而成之二胺基二羥基二苯基化合物(二胺基二羥基二苯基碸或二胺基二羥基二苯基醚)。這些化合物中之胺基及羥基在苯基上之取代位置,以任一者在3-位置,其他在4-位置為佳,其中以3-位置為胺基、4-位置為羥基取代之化合物為較佳(即,3,3’-二胺基-4,4’-二羥基二苯基碸或3,3’-二胺基-4,4’-二羥基二苯基醚)。
二胺基化合物(b)乃上述胺基酚類(a)以外之化合物中,一分子中含有兩個胺基之化合物就別無限制。
例如可經C1至C4烷基取代之伸苯基二胺,兩個胺基取代苯基(苯環上可經C1至C4烷基或C1至C4烷氧基取代)直接或經由交聯基(例如-O-、-O-C6
H4
-O-、-S-、-SO2
-、-CO2
-或具有歧鏈之C1至C10伸烷基等)結合而成之二胺基二苯基化合物,C1至C10脂肪族二胺等。又,有時也可以使用矽氧二胺等。
較佳為經由上述交聯基結合之二胺基二苯基化合物或異佛爾酮二胺。該二胺基二苯基化合物之較佳交聯基,例如-O-、-O-C6
H4
-O-、-SO2
-或具有歧鏈之C1至C10伸烷基等,更佳之交聯基為-O-、-O-C6
H4
-O-、或-SO2
-。
二胺基化合物(b)之具體例如間-苯二胺、對-苯二胺、間-甲苯二胺、4,4’-二胺基二苯基醚、3,3’-二甲基-4,4’-二胺基二苯基醚、3,4’-二胺基二苯基醚、4,4’-二胺基二苯基硫醚、3,3’-二甲基-4,4’-二胺基二苯基硫醚、3,3’-二乙氧基-4,4’-二胺基二苯基硫醚、3,3’-二胺基二苯基硫醚、4,4’-二胺基二苯甲酮、3,3’-二甲基-4,4’-二胺基二苯甲酮、3,3’-二胺基二苯基甲烷、4,4’-二胺基二苯基甲烷、3,4’-二胺基二苯基甲烷、3,3’-二甲氧基-4,4’-二胺基二苯基硫醚、2,2’-雙(3-胺基苯基)丙烷、2,2’-雙(4-胺基苯基)丙烷、4,4’-二胺基二苯基亞碸、3,3’-二胺基二苯基碸、4,4’-二胺基二苯基碸、聯苯胺、3,3’-二甲基聯苯胺、3,3’-二甲氧基聯苯胺、3,3’-二胺基聯苯、對-甲苯二胺、間-甲苯二胺、鄰-甲苯二胺、2,2’-雙(3-胺基苯氧基苯基)丙烷、2,2’-雙(4-胺基苯氧基苯基)丙烷、1,3-雙(4-胺基苯氧基苯基)苯、1,3-雙(3-胺基苯氧基)苯、1,3’-雙(3-胺基苯氧基苯基)丙烷、雙(4-胺基-3-甲基苯基)甲烷、雙(4-胺基-3,5-二甲基苯基)甲烷、雙(4-胺基-3-乙基苯基)甲烷、雙(4-胺基-3,5-二乙基苯基)甲烷、雙(4-胺基-3-丙基苯基)甲烷、雙(4-胺基-3,5-二丙基苯基)甲烷、異佛爾酮二胺、己二胺或三甲基己二胺等為較佳。又,有時也可使用矽氧二胺等。上述可使用1種或2種以上混合使用。上述中,以二胺基二苯基醚、異佛爾酮二胺或雙胺基苯氧基苯為更佳。
四元酸二酐(c),祇要分子中至少具有兩個酸酐架構皆可使用,例如均苯四甲酸酐、乙二醇-雙(偏苯三酸酐)、甘油-雙(偏苯三酸酐)單乙酸酯、1,2,3,4-丁烷四羧酸二酐、3,3’,4,4’-二苯基碸四羧酸二酐、3,3’,4,4’-二苯甲酮四羧酸二酐、3,3’,4,4’-聯苯四羧酸二酐、3,3’,4,4’-二苯基醚四羧酸二酐、2,2-雙(3,4-脫水二羧基苯基)丙烷、2,2-雙(3,4-脫水二羧基苯基)六氟丙烷、二環[2.2.2]辛-7-烯-2,3,5,6-四羧酸二酐、二環[2.2.2]辛烷-2,3,5,6-四羧酸二酐、5-(2,5-二氧基四氫-3-呋喃基)-3-甲基環己烯-1,2-二羧酸酐、或3a,4,5,9b-四氫-5-(四氫-2,5-二氧基-3-呋喃基)-萘并[1,2-c]呋喃-1,3-二酮等。其中,以兩個苯環上各具有一個酸酐基,且該苯環係直接鍵結,或經由-O-、-SO2
-或-CO-而結合之四羧酸二酐為較佳,自3,3’,4,4’-二苯基碸四羧酸二酐、3,3’,4,4’-二苯甲酮四羧酸二酐、3,3’,4,4’-聯苯四羧酸二酐及3,3’,4,4’-二苯基醚四羧酸二酐所成組群中選擇之化合物為更佳。尤其以3,3’,4,4’-二苯基碸四羧酸二酐、3,3’,4,4’-聯苯基四羧酸二酐或3,3’,4,4’-二苯基醚四羧酸二酐為最佳。
聚醯亞胺樹脂(A)可依照常法製成。例如按照專利文獻2所記載方法,由四元酸二酐及胺基酚類(a)及二胺基化合物(b)(以下併稱為二胺成分),較佳以γ-戊內酯等內酯和鹼(例如吡啶或N-甲基嗎啉等)作為觸媒的存在下,經縮聚合反應而製成聚醯亞胺樹脂(A)。此處,四元酸二酐和二胺成分之使用比率以二胺成分/四元酸二酐=0.5至2(莫耳比)為佳,其中以二胺成分/四元酸二酐=0.8至1.5(莫耳比)為較佳。又,視情況而定,對於二胺成分而言,有時使用稍稍過量之四元酸二酐為佳。
二胺成分(上述(a)成分及(b)成分)中之胺基酚類(a)之比率宜為1至95莫耳%,其中,以1至70莫耳%為較佳,更佳為3至60莫耳%,殘餘之5至99莫耳%,其中以30至99%為較佳,以40至97%為二胺基化合物(b)為更佳。又視情況而定,有時該胺基酚類(a)之比率可為50至95莫耳%,以較多於50莫耳%而低於92莫耳%為較佳。殘餘之5至50莫耳%中,以8至未達50莫耳%為二胺基化合物(b)為較佳。
上述聚醯亞胺樹脂(A)之合成中,上述縮聚合反應在觸媒(上述內酯及鹼等)之存在下進行時,官能基之酚性羥基在沒有保護下,容易製造直鏈狀之芳族聚醯亞胺共聚物(即,上述聚醯亞胺樹脂(A))。此乃在該觸媒之存在下進行該縮合反應時,該酚性羥基和例如酸酐或胺基等其他反應基不發生反應而進行該縮合反應所致。
上述觸媒所使用內酯以γ-戊內酯、鹼以吡啶或/及N-甲基嗎啉為較佳。
該聚醯亞胺樹脂(A)之合成時所使用溶劑,例如甲基乙基酮、甲基丙基酮、甲基異丙基酮、甲基丁基酮、甲基異丁基酮、甲基正己基酮、二乙基酮、二異丙基酮、二異丁基酮、環戊酮、環己酮、甲基環己酮、乙醯基丙酮、γ-丁內酯、雙丙酮醇、環己烯-1-酮、丙醚、異丙醚、丁醚、四氫呋喃、四氫哌喃、乙基異戊基醚、乙基第三丁基醚、乙基苯甲基醚、甲苯酚甲基醚、苯甲醚、苯乙醚、乙酸甲酯、乙酸乙酯、乙酸丙酯、乙酸異丙酯、乙酸丁酯、乙酸異丁酯、乙酸戊酯、乙酸異戊酯、乙酸2-乙己酯、乙酸環己酯、乙酸甲環己酯、乙酸苯甲酯、乙醯基乙酸甲酯、乙醯基乙酸乙酯、丙酸甲酯、丙酸乙酯、丙酸丁酯、丙酸苯甲酯、丁酸甲酯、丁酸乙酯、丁酸異丙酯、丁酸丁酯、丁酸異戊酯、乳酸甲酯、乳酸乙酯、乳酸丁酯、異戊酸乙酯、異戊酸異戊酯、草酸二乙酯、草酸二丁酯、苯甲酸甲酯、苯甲酸乙酯、苯甲酸丙酯、水楊酸甲酯、N-甲基吡咯烷酮、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、二甲亞碸等,惟非侷限於上述範圍。上述溶劑可單獨使用或2種以上混合使用。其中以γ-丁內酯等酮系溶劑為較佳,尤以具有4至5員環之環狀酮為更佳。
聚醯亞胺樹脂(A)之製造方法具體說明如下。
在氮氣等惰性氣體氛圍中,在上述觸媒及溶劑之混合溶劑中,按照上述比率添加二胺成分及四元酸二酐,繼之,一面蒸餾去除反應所產生之水(伴隨形成醯亞胺環產生之水)下,加熱攪拌,充分反應而得聚醯亞胺樹脂(A)溶液。此時,可混合甲苯等做為脫水劑。反應溫度通常以120至230℃為佳。反應時間大受反應溫度的影響,無論何種情形下,攪拌反應系到可得顯示出最高聚合度之最高黏度為佳,一般需時數分種至20小時。又,所得溶液投入甲醇及己烷等貧溶劑中,分離所產生聚合物後,以再沈澱法等進行精製,去除副產物而可得精製之聚醯亞胺樹脂(A)。
上述所得聚醯亞胺樹脂(A)之較佳活性氫原子當量為200至1500g/eq,其中以200至600g/eq為較佳,最佳為250至550g/eq左右。又,重量平均分子量(凝膠滲透色譜法以聚苯乙烯換算而得,下文中皆同)以大於50000為佳,例如51000至150000左右為較佳,更佳為56000至150000左右。有時候,可在56000至100000左右。
本發明之熱硬化性樹脂組成物,除聚醯亞胺樹脂(A)以外,尚含有環氧樹脂(B)成分。
做為環氧樹脂(B)可使用之環氧樹脂,祇要一分子中含有兩個以上之環氧基別無限制,但就機械強度,難燃性等之觀點而言,以具有苯環、聯苯環、萘環等芳環之環氧樹脂為佳。具體言之,酚醛清漆型環氧樹脂、含二甲苯架構之酚/酚醛清漆型環氧樹脂、含聯苯架構之酚醛清漆型環氧樹脂、雙酚A型環氧樹脂、雙酚F型環氧樹脂、四甲基聯苯型環氧樹脂、三苯基甲烷型環氧樹脂、乙二醛型環氧樹脂等,唯非侷限於上述範圍。乙二醛型環氧樹脂乃係較佳之一種。
本發明之熱硬化性樹脂組成物中之硬化劑,除具有酚性羥基之聚醯亞胺樹脂(A)之外,尚可併用其他硬化劑。可併用之硬化劑之具體例如二胺基二苯基甲烷、二伸乙基三胺、三伸乙基四胺、二胺基二苯基碸、異佛爾酮二胺、二氰基二醯胺、亞麻酸二聚體和伸乙基二胺所合成之聚醯亞胺樹脂、酞酸酐、偏苯三酸酐、均苯四甲酸酐、馬來酸酐、四氫酞酸酐、甲基四氫酞酸酐、甲基卡比酸酐、六氫酞酸酐、甲基六氫酞酸酐、酚/酚醛清漆樹脂、三苯基甲烷及其改質物、咪唑、三氟化硼/胺配位化合物、胍衍生物等,唯非侷限於上述範圍。這些在併用時,總硬化劑中聚醯亞胺樹脂(A)所占比率,一般為20重量%以上(下文中,倘無特別說明,皆指重量%),其中以30%以上為較佳,以50%為更佳。聚醯亞胺樹脂(A)之比率在50%以上至100%範圍為更佳。一般,單獨使用聚醯亞胺樹脂(A)為較佳。
本發明之熱硬化性樹脂組成物中,硬化劑之使用量,以環氧樹脂之環氧基1當量計,使用0.7至1.2活性氫當量為佳。當對於1當量環氧基計,未達0.7活性氫當量時,或相反地超過1.2活性氫當量時,硬化皆不完整而有得不到優良之硬化物性之虞。具有酚性羥基之聚醯亞胺樹脂(A)之活性氫當量,可由反應時所供料之二胺成分及四元酸二酐之比率,按照下述方法計算之。
{二胺成分(上述(a)成分及(b)成分)及四元酸二酐之合計供料重量-醯亞胺化時所產生水之重量}/胺基酚類(a)之羥基莫耳數。
又,本發明之熱硬化性樹脂組成物中之聚醯亞胺樹脂(A)及環氧樹脂(B)之重量比率,分別由所使用化合物之活性氫當量或環氧當量而異,無法一概而言,一般對於100重量份(下文中,倘無特別說明,皆指重量份)之聚醯亞胺樹脂(A),使用1至100重量份之環氧樹脂為宜,其中以25至100重量份為較佳,以30至100重量份為更佳,最佳為50至100重量份範圍。
又,本發明之熱硬化性樹脂組成物中,必要時,可含有硬化促進劑。一般以含有硬化促進劑為較佳。該硬化促進劑之具體例如2-甲基咪唑、2-乙基咪唑、2-乙基-4-甲基咪唑、2-苯基-4,5-二羥基甲基咪唑、2-苯基-4-甲基-5-羥甲基咪唑等咪唑類,2-(二甲基胺基甲基)酚、1,8-二吖雙環(5,4,0)十一烯-7等三級胺類,三苯膦等膦類,辛酸錫等之金屬化合物等。一般以咪唑類為較佳。對於100重量份之環氧樹脂(B)計,必要時可使用0.1至5.0重量份之硬化促進劑。
本發明之熱硬化性樹脂組成物,必要時可含有無機填充材料。該無機填充材料之具體例如氧化矽、氧化鋁或滑石等。本發明之環氧樹脂組成物中,可使用0至90重量%之無機填充材料。本發明之熱硬化性樹脂組成物中,硬化促進劑及無機填充劑之外,尚可使用其他添加劑,例如矽烷偶合劑、硬脂酸、棕櫚酸、硬脂酸鋅或硬脂酸鈣等脫模劑,顏料等種種添加劑,必要時可含有之。
本發明之熱硬化性樹脂組成物由均一混合上述各成分而得。本發明之熱硬化性樹脂組成物可藉已往周知方法容易製成其硬化物。例如環氧樹脂和硬化劑,必要時,再加上硬化促進劑,無機填充材料及其他添加劑,必要時使用擠壓機、捏合機或輥等,充分混合至均一而得本發明之熱硬化性樹脂組成物。所得環氧樹脂組成物藉熔融注型法、轉移成型法、注射成型法或壓縮成型法等成型,再於80至200℃下加熱2至10小時,而得本發明之硬化物。
本發明之清漆乃含有溶劑之熱硬化性樹脂組成物,也包含在本發明之熱硬化性樹脂組成物中。本發明之清漆,例如可將合成聚醯亞胺樹脂(A)時所得含有聚醯亞胺樹脂(A)之反應液(即,聚醯亞胺樹脂(A)溶液),不分離該樹脂(A)之下,混合環氧樹脂(B)以及必要時混合其他成分而製成。此方法簡便而最佳。又,使用分離而得之聚醯亞胺樹脂(A),加入溶劑,環氧樹脂(B),以及必要時再加上其他成分,以任意適當順序混合而製得該清漆。例如,首先如同上述調製不含溶劑之熱硬化性樹脂組成物,之後,再混合溶劑成為清漆亦行。又,必要時,使用再沈澱法等精製之樹脂(A)調製成清漆。清漆中之固形物濃度(指溶劑以外成分之濃度,下文中皆同)乃對於整個清漆而言,通常在3至80%為宜,其中較佳為5至50%,其餘為溶劑。或有時,該固形物濃度可達20至85%,其中,以30至85%為較佳,更佳為30至60%。又,該清漆中,聚醯亞胺樹脂(A)含量以清漆總量計,宜在2至45%,通常為5至40%,以10至40%為較佳,更佳為15至35%左右,最佳為20至30%。環氧樹脂(B)含量,對整個清漆而言,為1至35%,一般為5至30%,其中以10至30%為較佳,更佳為10至25%左右。其餘為任意成分及溶劑,任意成分含量,對於整清漆而言,可含有0至60%範圍,至少對於整個清漆而言,溶劑占30%以上,其中以40%以上且75%以下為較佳。各成分在上述範圍內,且各成分合計成為100%之下調製之。
本發明之片狀物,可由上述清漆藉各種塗布方法,例如其本身為周知之照相凹版塗布法,網版印刷法,金屬遮蔽法,旋轉塗布法等塗布在平面狀支持體上,乾燥後成為所定之厚度,例如5至100 μ m,其中以10至100 μ m為較佳,塗布後乾燥而得,必要時尚可加熱硬化該塗膜層。採用那一種塗布法,視平面狀支持體之基材種類,形狀或大小,或塗膜厚度等而選擇適當方法進行。基材之例如聚醯胺、聚醯亞胺、聚芳酯化合物、聚對苯二甲酸伸乙酯(PET)、聚對苯二甲酸伸丁酯、聚醚醚酮、聚醚醯亞胺、聚醚酮、聚酮、聚乙烯、聚丙烯等各種高分子及/或其共聚物等。該平面狀支持體乃係由該基材製成之薄膜,或銅箔等金屬箔等。其中以聚醯亞胺膜或金屬箔為較佳。上述經塗布乾燥所得片狀物中之本發明之樹脂組成物,藉加熱塗膜,使之硬化而得片狀之硬化物。特別是可將上述支持體做為剝離薄膜供結合片等使用。本發明之片狀物之較佳用途為可彎曲性印刷配線用基材、被覆膜材料、結合片、補強板等可彎曲性印刷布線板材料等。
又,本發明之清漆可含浸於玻璃纖維、碳纖維、聚酯纖維、氧化鋁纖維、紙等基材中,加熱乾燥所得預浸物,再熱壓成形也可得硬化物。使用於上述含浸時,清漆中之固形物濃度以30至90%為佳,其中以30至85%為更佳。
本發明藉實施例具體說明如下。唯本發明不侷限於下列實施例範圍。
備有攪拌裝置、迴流管、水分截留器、溫度計之3L燒瓶中,利用氮氣沖掃處理,然後放入1364.3g之γ-丁內酯做為溶劑,再加入365.4g(1.02莫耳)之3,3’,4,4’-二苯基碸四羧酸二酐(簡稱DSDA,新日本理化公司製品,分子量為358.28),139.3g(0.60莫耳)之3,3’-二胺基-4,4’-二羥基二苯基醚(簡稱ADPE,日本化藥公司製品,分子量為232.24),80.0g(0.40莫耳)之4,4’-二胺基二苯基醚(簡稱DADE,和歌山精化公司製品,分子量為200.00),觸媒使用γ-戊內酯10.0g及吡定15.8g,脫水劑使用甲苯20g,供料後在180℃下,一面除去水分,一面攪拌,反應8小時而得含有30%之具有酚性羥基之聚醯亞胺樹脂之樹脂溶液(該溶液簡稱為A-1)。
又,該聚醯亞胺樹脂之活性氫當量為457.40g/eq,平均重量分子量為78000,兩末端為酸酐基。
備有攪拌裝置、迴流管、水分截留器及溫度計之3L燒瓶中,利用氮氣沖掃處理,然後供料以1349.3g之γ-丁內酯為溶劑,308.96g(1.05莫耳)之3,3’,4,4’-聯苯四羧酸二酐(BPDA,宇部興產公司製品,分子量為294.25),252.3g(0.90莫耳)之3,3’-二胺基-4,4’-二羥基二苯基碸(ABPS,日本化藥公司製品,分子量為280.3),17.0g(0.10莫耳)之異佛爾酮二胺(德克沙休斯公司製品,分子量為170.25),γ-戊內酯10.0g及吡定15.8g為觸媒,甲苯20g為脫水劑,在180℃下一面除去水,一面攪拌下反應8小時,而製得含有30%之具有酚性羥基之聚醯亞胺樹脂之樹脂溶液(下文中稱為A-2)。
又,該聚醯亞胺樹脂之活性氫當量為301.22g/eq,平均重量分子量為61000,兩末端為酸酐基。
備有攪拌裝置、迴流管、水分截留器及溫度計之3L燒瓶中,利用氮氣沖掃處理,然後供料以1400.77g之γ-丁內酯,365.4g之3,3’,4,4’-二苯基碸四羧酸二酐(ODPA,新日本理化公司製品,分子量為358.28),316.42g(1.02莫耳)之3,3’,4,4’-二苯基四羧酸二酐(ADPE,馬納克公司製品,分子量為310.22),196.21g(0.70莫耳)之ABPS,87.70g(0.10莫耳)之1,3-雙(3-胺基苯氧基)苯(APB-N,三井化學公司製品,γ-戊內酯10.21g及吡啶16.14g為觸媒,甲苯20g為脫水劑,在180℃下,一面除去水分,一面攪拌,反應8小時而得含有30%之具有酚性羥基之聚醯亞胺樹脂之樹脂溶液(此溶液稱為A-3)。
又,聚醯亞胺樹脂之活性氫當量為403.09g/eq,平均重量分子量為90900,兩末端為酸酐基。
使用日本化藥公司製品之NC-3000H(聯苯-酚縮合型環氧樹脂,環氧當量為290g/eq,軟化點為70℃)為環氧樹脂,上述合成例1及合成例2所得溶液(A-1),溶液(A-2)及日本化學公司製品之GPH-78(酚-乙二醛縮合型樹脂,羥基當量為230g/eq,軟化點為78℃)為硬化劑,2-苯基-4,5-二羥基甲基咪唑(2PHZ)為硬化促進劑,表1中所示配方比率(單位為「份」)混合,而得本發明之熱硬化性樹脂組成物。
又,實施例1及2所使用之環氧樹脂之環氧當量值兩者皆為0.345當量,該聚醯亞胺樹脂之活性氫當量值分別為0.367當量及0.368當量。
保管上述清漆(1)、(2)及(3)於60℃,調查凝膠化所需日數之結果,該清漆(1)及(2)經過1星期也未凝膠化,但是清漆(3)經2日就凝膠化。
上述清漆(1)、(2)及(3)分別在PET膜(聚酯膜)上以乾燥後之厚度成為50 μ m之方式塗布,在180℃下加熱硬化1小時,除去PET膜而分別獲得片狀試料(膜(1)、(2)及(3))。
膜(1)及(2)皆屬彎曲也不會裂開而充分具有柔軟性之膜。另一方面,膜(3)一旦彎曲就斷裂。又所得膜分別切取1cm寬之試料,藉MIT試驗儀(JIS P8115之「耐折性」項所記載之MIT試驗儀)加重500g,彎曲角度135°進行彎曲性試驗之結果,膜(1)及(2)彎曲300次以上也未斷裂,但是膜(3)僅彎曲1次就斷裂了。
由上述可知本發明之清漆具有形成具備充分之柔軟性之薄膜之功能。
其次,實施例3所得試料,依照UL94-VTM(美國Underwriters Laboratories公司所規定安全標準之一)進行難燃性試驗之結果,片(1)及(2)屬於V-0,但是片(3)在一瞬間就燃盡。又,難燃性評估之V-0乃屬上述試驗中之「難燃性」層級之評估。
實施例1中,替代560份量之(A-1)溶液,而改用494.3份量之合成例3所得(A-3)溶液之外,皆按照實施例1相同方法進行,而得本發明之熱硬化性組成物。所得清漆在60℃下保管1星期也未凝膠化。
又,本實施例中所使用環氧樹脂之環氧當量值為0.345當量,該聚醯亞胺樹脂之活性氫當量為0.368當量。
由上述結果顯示本發明之熱硬化性樹脂組成物具有優異之貯存安定性,且可得難燃性及耐熱性優異之硬化物,同時使用該組成物形成之膜具有充分之柔軟性及耐彎曲性。
Claims (15)
- 一種熱硬化性樹脂組成物,其特徵為含有具酚性羥基之聚醯亞胺樹脂(A)及環氧樹脂(B),該聚醯亞胺樹脂(A)之含有比率,對於環氧樹脂(B)中之環氧基1當量計,該聚醯亞胺樹脂(A)中之活性氫當量成為0.7至1.2當量,其中,具酚性羥基之聚醯亞胺樹脂(A)係由具有酚性羥基之二胺成分(下文中,稱為胺基酚類(a))、不具有酚性羥基之二胺成分(下文中,稱為二胺基化合物(b))及四元酸二酐(c)製造而成,其中,胺基酚類(a)為由3,3’-二胺基-4,4’-二羥基二苯基碸、3,3’-二胺基-4,4’-二羥基二苯基醚、3,3’-二胺基-4,4’-二羥基聯苯、2,2-雙(3-胺基-4-羥基苯基)丙烷、1,3-六氟-2,2-雙(3-胺基-4-羥基苯基)丙烷及9,9’-雙(3-胺基-4-羥基苯基)芴所成組群中選擇之一種以上者。
- 如申請專利範圍第1項之熱硬化性樹脂組成物,其中,聚醯亞胺樹脂(A)係在其架構中具有磺醯基者。
- 如申請專利範圍第1項之熱硬化性樹脂組成物,其中,環氧樹脂(B)包括由酚醛清漆型環氧樹脂、含有伸二甲苯架構之酚/酚醛清漆型環氧樹脂、含有聯苯架構之酚醛清漆型環氧樹脂、雙酚A型環氧樹脂、雙酚F型環氧樹脂、四甲基聯酚型環氧樹脂、三苯基甲烷型環氧樹脂及乙二醛型環氧樹脂所成組群中選擇一種以上。
- 如申請專利範圍第1項至第3項中任一項之熱硬化性樹脂組成物,其中,係含有硬化促進劑。
- 一種清漆,其特徵為含有如申請專利範圍第1項至第3項中任一項之熱硬化性樹脂組成物及溶劑。
- 一種片狀物,其特徵為在平面狀支持體之兩面或一面具有由如申請專利範圍第1項至第3項中任一項之組成物所構成之層。
- 如申請專利範圍第6項之片狀物,其中,該平面狀支持體係聚醯亞胺膜、金屬箔或剝離薄膜。
- 一種預浸物(prepreg),其特徵為於基材含浸如申請專利範圍第5項之清漆,經乾燥而得者。
- 一種硬化物,其特徵為如申請專利範圍第1項至第3項中任一項之熱硬化性樹脂組成物經硬化而成者。
- 一種熱硬化性樹脂組成物,其特徵為含有具酚性羥基之聚醯亞胺樹脂(A)及環氧樹脂(B),該具酚性羥基之聚醯亞胺樹脂(A)係由胺基酚類(a)、二胺基化合物(b)及四元酸二酐(c)所製造而成,該胺基酚類(a)為由3,3’-二胺基-4,4’-二羥基二苯基碸、3,3’-二胺基-4,4’-二羥基二苯基醚、3,3’-二胺基-4,4’-二羥基聯苯、2,2-雙(3-胺基-4-羥基苯基)丙烷、1,3-六氟-2,2-雙(3-胺基-4-羥基苯基)丙烷及9,9’-雙(3-胺基-4-羥基苯基)芴所成組群中選擇之一種以上者,該二胺基化合物(b)係由間苯二胺、對苯二胺、間甲苯二胺、4,4’-二胺基二苯基醚、3,3’-二甲基-4,4’-二胺基二苯基醚、3,4’-二胺基二苯基醚、4,4’-二胺基二苯基硫醚、3,3’-二甲基-4,4’-二胺基二苯基硫醚、3,3’-二乙氧基-4,4’-二 胺基二苯基硫醚、3,3’-二胺基二苯基硫醚、4,4’-二胺基二苯甲酮、3,3’-二甲基-4,4’-二胺基二苯甲酮、3,3’-二胺基二苯基甲烷、4,4’-二胺基二苯基甲烷、3,4’-二胺基二苯基甲烷、3,3’-二甲氧基-4,4’-二胺基二苯基硫醚、2,2’-雙(3-胺基苯基)丙烷、2,2’-雙(4-胺基苯基)丙烷、4,4’-二胺基二苯亞碸、3,3’-二胺基二苯基碸、4,4’-二胺基二苯基碸、聯苯胺、3,3’-二甲基聯苯胺、3,3’-二甲氧基聯苯胺、3,3’-二胺基聯苯、對二甲苯二胺、間二甲苯二胺、鄰二甲苯二胺、2,2’-雙(3-胺基苯氧基苯基)丙烷、2,2’-雙(4-胺基苯氧基苯基)丙烷、1,3-雙(4-胺基苯氧基苯基)苯、1,3’-雙(3-胺基苯氧基苯基)丙烷、雙(4-胺基-3-甲基苯基)甲烷、雙(4-胺基-3,5-二甲基苯基)甲烷、雙(4-胺基-3-乙基苯基)甲烷、雙(4-胺基-3,5-二乙基苯基)甲烷、雙(4-胺基-3-丙基苯基)甲烷、雙(4-胺基-3,5-二丙基苯基)甲烷、聚矽氧二胺、異佛爾酮二胺、己二胺或三甲基己二胺所成組群中選擇一種或二種以上而成。
- 如申請專利範圍第1項之熱硬化性樹脂組成物,其中,對於100重量份之該聚醯亞胺樹脂(A)而計,含有30至100重量份之環氧樹脂(B)。
- 一種熱硬化性樹脂組成物,其特徵為含有具酚性羥基之聚醯亞胺樹脂(A)及環氧樹脂(B),該具酚性羥基之聚醯亞胺樹脂(A)係由胺基酚類(a)、二胺基化合物(b)及四元酸二酐(c)所製造而成,胺基酚類(a)係為,3,3’-二 胺基-4,4’-二羥基二苯基醚或3,3’-二胺基-4,4’-二羥基二苯基碸,而二胺基化合物係2個之胺基取代苯基(苯環可經C1至C4烷基或C1至C4烷氧基取代)直接結合或經由交聯基結合而成之二胺基二苯基化合物。
- 如申請專利範圍第1項之熱硬化性樹脂組成物,其中,該具酚性羥基之聚醯亞胺樹脂(A)係由3,3’,4,4’-二苯基碸四羧酸二酐及3,3’-二胺基-4,4’-二羥基二苯基醚以及4,4’-二胺基二苯基醚之縮聚合,或3,3’,4,4’-聯苯四羧酸二酐及3,3’-二胺基-4,4’-二羥基二苯基碸以及異佛爾酮二胺之縮聚合而製得者。
- 如申請專利範圍第12項之熱硬化性樹脂組成物,其中,該二胺基化合物之交聯基係-O-、-O-C6 H4 -O-、-SO2 -或可具有歧鏈之C1至C10伸烷基。
- 如申請專利範圍第12項之熱硬化性樹脂組成物,其中,該二胺基化合物包括由4,4’-二胺基二苯基醚、1,3-雙(3-胺基苯氧基)苯及異佛爾酮二胺所成組群中選擇至少一種者。
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Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100463115C (zh) * | 2004-05-18 | 2009-02-18 | 日立化成工业株式会社 | 粘接接合片与使用该粘接接合片的半导体装置以及其制造方法 |
TWI417311B (zh) | 2005-10-21 | 2013-12-01 | Nippon Kayaku Kk | 熱硬化性樹脂組成物及其用途 |
JPWO2007148666A1 (ja) * | 2006-06-20 | 2009-11-19 | 日本化薬株式会社 | プライマー樹脂層付銅箔及びそれを使用した積層板 |
US8410620B2 (en) | 2007-09-20 | 2013-04-02 | Nippon Kayaku Kabushiki Kaisha | Primer resin for semiconductor device and semiconductor device |
JP5796712B2 (ja) | 2009-04-23 | 2015-10-21 | 日産化学工業株式会社 | ポリヒドロキシイミドの製造方法 |
JP5733778B2 (ja) * | 2009-06-11 | 2015-06-10 | 日本化薬株式会社 | プライマー層用ポリイミド樹脂及びそれを用いた積層板 |
KR101050370B1 (ko) * | 2009-08-18 | 2011-07-20 | 한국화학연구원 | 폴리이미드를 포함하는 유기절연체 형성용 조성물, 및 이를 이용한 유기절연체 및 유기박막트랜지스터 |
TWI401252B (zh) | 2010-06-22 | 2013-07-11 | Chi Mei Corp | 液晶配向劑,以及以其製得的液晶配向膜與液晶顯示元件 |
TWI465483B (zh) * | 2010-12-28 | 2014-12-21 | Chi Mei Corp | 液晶配向劑,液晶配向膜,及含有該液晶配向膜的液晶顯示元件 |
RU2510408C1 (ru) * | 2012-10-23 | 2014-03-27 | Российская Федерация в лице Министерства промышленности и торговли Российской Федерации (Минпромторг России) | Полимерное связующее и препрег на его основе |
JP2014218651A (ja) * | 2013-04-08 | 2014-11-20 | Jnc株式会社 | 熱硬化性組成物 |
KR101734425B1 (ko) | 2013-09-24 | 2017-05-11 | 주식회사 엘지화학 | 드라이 필름 솔더 레지스트의 제조 방법과, 이에 사용되는 필름 적층체 |
US20160194542A1 (en) * | 2013-10-23 | 2016-07-07 | Nippon Kayaku Kabushiki Kaisha | Polyimide resin composition, and heat-conductive adhesive film produced using same |
JP6086537B2 (ja) * | 2013-10-30 | 2017-03-08 | 日本化薬株式会社 | ポリイミド樹脂 |
US11846885B2 (en) * | 2013-12-30 | 2023-12-19 | Rohm And Haas Electronic Materials, Llc | Topcoat compositions and photolithographic methods |
JP6728680B2 (ja) * | 2014-10-10 | 2020-07-22 | 東レ株式会社 | 耐熱性不織布およびその製造方法 |
TWI544030B (zh) * | 2014-12-02 | 2016-08-01 | 奇美實業股份有限公司 | 軟性基板用組成物及軟性基板 |
JP6597471B2 (ja) * | 2016-05-02 | 2019-10-30 | 信越化学工業株式会社 | 大面積の半導体素子搭載基材を封止する方法 |
US10197918B2 (en) * | 2016-10-31 | 2019-02-05 | Rohm And Haas Electronic Materials Llc | Photoresist topcoat compositions and methods of processing photoresist compositions |
TWI630234B (zh) * | 2017-01-16 | 2018-07-21 | 臻鼎科技股份有限公司 | 樹脂組合物及應用該樹脂組合物的聚醯亞胺膜及電路板 |
KR102671097B1 (ko) * | 2017-05-31 | 2024-05-30 | 세키스이가가쿠 고교가부시키가이샤 | 경화성 수지 조성물, 경화물, 접착제, 접착 필름, 커버레이 필름, 및, 프린트 배선판 |
WO2020189354A1 (ja) * | 2019-03-15 | 2020-09-24 | 日本化薬株式会社 | ポリアミック酸樹脂、ポリイミド樹脂およびこれらを含む樹脂組成物 |
CN113999490A (zh) * | 2021-11-09 | 2022-02-01 | 中国科学院山西煤炭化学研究所 | 一种韧性环氧树脂体系及其制备方法和应用 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5677393A (en) * | 1992-12-28 | 1997-10-14 | Nippon Steel Chemical Co., Ltd. | Heat-resistant film adhesive for use in fabrication of printed circuit boards and process for using the same |
JP2002003715A (ja) * | 2000-06-26 | 2002-01-09 | Kanegafuchi Chem Ind Co Ltd | 組成物とそれを用いた感光性組成物及びカバーレイフィルム |
US20040019174A1 (en) * | 2002-07-19 | 2004-01-29 | Nobuhiro Ichiroku | Phenolic hydroxyl-bearing polyimide resin, making method and polyimide resin composition |
JP2004035650A (ja) * | 2002-07-01 | 2004-02-05 | Gun Ei Chem Ind Co Ltd | ポリイミド樹脂、これを含有する樹脂組成物、電子部品用被覆材料及び電子部品用接着剤 |
US20040176526A1 (en) * | 2001-07-09 | 2004-09-09 | Kanji Shimo-Ohsako | Resin composition |
Family Cites Families (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4629777A (en) | 1983-05-18 | 1986-12-16 | Ciba-Geigy Corporation | Polyimides, a process for their preparation and their use |
US5037691A (en) | 1986-09-15 | 1991-08-06 | Compositech, Ltd. | Reinforced plastic laminates for use in the production of printed circuit boards and process for making such laminates and resulting products |
JPH01245586A (ja) | 1988-03-28 | 1989-09-29 | Nippon Steel Chem Co Ltd | フレキシブルプリント基板 |
US4937133A (en) | 1988-03-28 | 1990-06-26 | Nippon Steel Chemical Co., Ltd. | Flexible base materials for printed circuits |
JPH02180980A (ja) | 1989-01-04 | 1990-07-13 | Toshiba Chem Corp | フイルム接着剤 |
US5268447A (en) | 1990-06-01 | 1993-12-07 | Mitsui Toatsu Chemicals, Inc. | Readily processable polyimide and preparation process of same |
JPH04345682A (ja) | 1991-05-21 | 1992-12-01 | Sumitomo Bakelite Co Ltd | 気密封止用接着剤 |
JP2658632B2 (ja) | 1991-06-12 | 1997-09-30 | 信越化学工業株式会社 | 半導体封止用エポキシ樹脂成形材料接着用プライマー組成物 |
JP3646410B2 (ja) * | 1996-06-18 | 2005-05-11 | 宇部興産株式会社 | 積層基板 |
JPH1075053A (ja) | 1996-09-02 | 1998-03-17 | Mitsui Petrochem Ind Ltd | フレキシブル金属箔積層板の製造方法 |
JPH1081748A (ja) * | 1996-09-05 | 1998-03-31 | Nippon Steel Chem Co Ltd | ポリイミド含有多価フェノール性樹脂の製造方法並びにそのエポキシ樹脂組成物及びその硬化物 |
JP2000183239A (ja) | 1998-12-11 | 2000-06-30 | Toray Ind Inc | 半導体装置 |
JP3669429B2 (ja) | 2001-03-27 | 2005-07-06 | 信越化学工業株式会社 | 電極用組成物及び電極材 |
JP4102051B2 (ja) * | 2001-10-12 | 2008-06-18 | 株式会社カネカ | 積層体並びに多層プリント配線板 |
JP4071958B2 (ja) * | 2001-11-19 | 2008-04-02 | 株式会社カネカ | ポリイミド樹脂組成物 |
JP2003155325A (ja) * | 2001-11-21 | 2003-05-27 | Toto Kagaku Kogyo Kk | 耐熱性樹脂組成物 |
JP4180292B2 (ja) * | 2002-03-29 | 2008-11-12 | 株式会社カネカ | フィルム状接着剤、及び該接着剤を積層した積層部材 |
JP2003306649A (ja) | 2002-04-12 | 2003-10-31 | Kanegafuchi Chem Ind Co Ltd | 接着シート及びプリント配線板 |
JP4174274B2 (ja) | 2002-09-03 | 2008-10-29 | 群栄化学工業株式会社 | ポリアミドイミド樹脂、これを含有する樹脂組成物、電子部品用被覆材料及び電子部品用接着剤 |
JP4005006B2 (ja) * | 2003-09-04 | 2007-11-07 | 京セラケミカル株式会社 | 成形用耐熱性樹脂組成物 |
JP2005290327A (ja) | 2004-04-05 | 2005-10-20 | Kaneka Corp | 絶縁接着フィルムおよびこれを含む積層体、並びにプリント配線板 |
JP4709503B2 (ja) | 2004-05-20 | 2011-06-22 | 株式会社カネカ | フィラー含有樹脂組成物およびその利用 |
JP4767517B2 (ja) | 2004-09-14 | 2011-09-07 | 三菱瓦斯化学株式会社 | 樹脂複合銅箔とこれを用いた銅張積層板及びプリント配線板 |
US7892651B2 (en) | 2004-09-14 | 2011-02-22 | Mitsubishi Gas Chemical Company, Inc. | Resin composite metal foil, laminate and process for the production of printed wiring board using the laminate |
TWI417311B (zh) | 2005-10-21 | 2013-12-01 | Nippon Kayaku Kk | 熱硬化性樹脂組成物及其用途 |
JPWO2007148666A1 (ja) | 2006-06-20 | 2009-11-19 | 日本化薬株式会社 | プライマー樹脂層付銅箔及びそれを使用した積層板 |
-
2006
- 2006-10-18 TW TW95138352A patent/TWI417311B/zh not_active IP Right Cessation
- 2006-10-18 JP JP2007541000A patent/JP5276324B2/ja active Active
- 2006-10-18 KR KR1020087007689A patent/KR20080056177A/ko not_active Application Discontinuation
- 2006-10-18 CN CN2006800392711A patent/CN101291990B/zh not_active Expired - Fee Related
- 2006-10-18 US US12/083,588 patent/US8080319B2/en not_active Expired - Fee Related
- 2006-10-18 WO PCT/JP2006/320724 patent/WO2007046405A1/ja active Application Filing
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5677393A (en) * | 1992-12-28 | 1997-10-14 | Nippon Steel Chemical Co., Ltd. | Heat-resistant film adhesive for use in fabrication of printed circuit boards and process for using the same |
JP2002003715A (ja) * | 2000-06-26 | 2002-01-09 | Kanegafuchi Chem Ind Co Ltd | 組成物とそれを用いた感光性組成物及びカバーレイフィルム |
US20040176526A1 (en) * | 2001-07-09 | 2004-09-09 | Kanji Shimo-Ohsako | Resin composition |
JP2004035650A (ja) * | 2002-07-01 | 2004-02-05 | Gun Ei Chem Ind Co Ltd | ポリイミド樹脂、これを含有する樹脂組成物、電子部品用被覆材料及び電子部品用接着剤 |
US20040019174A1 (en) * | 2002-07-19 | 2004-01-29 | Nobuhiro Ichiroku | Phenolic hydroxyl-bearing polyimide resin, making method and polyimide resin composition |
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JP5276324B2 (ja) | 2013-08-28 |
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US8080319B2 (en) | 2011-12-20 |
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TW200724570A (en) | 2007-07-01 |
JPWO2007046405A1 (ja) | 2009-04-23 |
WO2007046405A1 (ja) | 2007-04-26 |
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