TWI335926B - Epoxy resin composition containing reactive phosphonate flame retardant and filler - Google Patents
Epoxy resin composition containing reactive phosphonate flame retardant and filler Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4071—Curing agents not provided for by the groups C08G59/42 - C08G59/66 phosphorus containing compounds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
- C08K5/523—Esters of phosphoric acids, e.g. of H3PO4 with hydroxyaryl compounds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
- H05K1/0373—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement containing additives, e.g. fillers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/34—Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C08L61/04, C08L61/18 and C08L61/20
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
- H05K2201/01—Dielectrics
- H05K2201/0104—Properties and characteristics in general
- H05K2201/012—Flame-retardant; Preventing of inflammation
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
- H05K2201/02—Fillers; Particles; Fibers; Reinforcement materials
- H05K2201/0203—Fillers and particles
- H05K2201/0206—Materials
- H05K2201/0209—Inorganic, non-metallic particles
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Description
1335926 玫、發明說明: 【發明所屬之技術領域】 本發明係關於環氧樹脂組合物,舉例而言,可使用該組 合物在電子用途之印刷配線板中。 【先前技術】 此組合物代表’舉例而言,對於頒予Shin Kobe電氣製造 有限公司/曰立化學有限公司之曰本專利公告案第
2001/302,879號中所述之該型组合物之新穎改良。 【發明内容】 本發明的組合物含有一種環氧樹脂作為一個主要組份。 此組份以組合物的總重量自約2〇重量%至約5〇重量%存在 較佳,此組份是含非齒素之環氧樹脂,例如雙酚A型之環 乳樹脂’或具有此通常型式的其他樹脂其對於製造印刷配 線板或此型的其他電子基板物質具有實用性(雙酚F環氧、 線型㈣(清漆)樹脂環氧、甲酚線型㈣(清漆)樹脂環氧及 /或雙酚A線形酚醛環氧樹脂)。 容混合物。
可採用任何此等樹脂的可相 一本:明的組合物之一種另外視需要,但是較佳组份是聚 本并Y井樹脂其數量為該組合物總重量的至高約重量% ::佳自約5重量%至約2。重量%。此組合物是—種熱固性 樹脂其含有一個二氫苯并十井環’此環係由下列所述之反 89288.doc 1335926 應所形成:
OH
十 Rl-NH3 + 2〇ΉΟ 〇^^N-Rl
此組份及其製造方法更進一 號中(第2列,59行至第3列, 中 〇 步記述於美國專利第5,945,222 62行),以引用的方式併入本文 本發明組合物的下—個另外視需要组份是前述樹脂組份 之共固化劑。可使用可相容之共固化劑的混合物。此共固 化劑可能以組合物的總重量,自約〇%至約2〇重量%存在, 較佳自約5重量%至約15重量%。代表性共固化劑包括酚曱 醛樹脂、曱酚曱醛樹脂、線型酚醛樹脂、線型酚醛樹脂/三 聚氰胺、磷酸化線型酚醛樹脂、三畊改質之線型酚醛樹脂 、雙氰胺及其類似物。 本發明的組合物亦含有一或數種無機填料物質其數量為 自約10重量❶/。至約5〇重量%。(各)填料物質可選自下列所熟 知之填料例如:滑石、矽石、礬土、氳氧化鋁、氫氧化鎂 、硼酸鋅及其類似物。適合本文中使用之較佳物質是礬土 三水合物。 雖然PCT公告之專利申請案第WO 03/029258號中教導: 環氧樹脂可含有羥基封端之低聚膦酸酯作為阻燃劑,但是 該PCT申請案一般顯示:此膦酸目旨的含量必須是接近環氧 樹脂的自約20重量%至約30重量%或更高才可獲得可接受 之結果。未述及使用填料在該等組合物中。依照本發明, 89288.doc 1335926 填料的附加存在可客許使用較低數量之膦酸醋添加劑。下 列表I中實例7舉例說明:僅需要·。之膦酸酿。使用 T許製造具有充分阻燃性之環氧組合物,儘管使用較低數 量、*酸阻燃劑’同時仍能產生具有良好物理性質之產 物(例如,較高之\,較佳之水解穩定性等)。 本發明組合物的每種前述之組份個別為通常熟諳此藝之 人士為知係本發明型的環氧組合物之潛在性組扮,且截至 月il為止彼等已以各種組合來採用,如前述之日本專利 申請案第2〇〇1/3〇2,879中所例示。 當與先前技藝方法比較(此等先前技藝方法依賴於先前 斤ϋ各‘且6的不同組合)時,形成本文中之新穎且係主要添 力训之反應性膦酸酯固化劑係以組合物總重量之自約3重 量%至,..勺40重量%存在,較佳自約5重量%至約⑽重量%。如 國’τ'專利么告案第w〇 〇3/〇29258號中更完全記述,此 阻U固化劑是_種低聚合之膦酸酯’其中包括重複單元 (〇)(R) Ο-伸芳基_並具有大於約12重量%之磷含量。該 組:物中《膦酸g旨物種同樣包括含有-OH端基者,可能具有 不3 _0H端基者。較佳之R基團是甲基,但可能是任何低碳 烷基基團。 按伸芳基意指二羥基酚的任何基團。較佳,該二羥基 酚應具有其兩個羥基基團在不接鄰之位置上。實例包括間 苯一酚、氫醌和雙酚類,例如雙酚A、雙酚F、4,4,-雙酚、 酚酞、4,4 -瓴代二酚或4,4,_磺醯基二酚。伸芳基基團可能 疋1,3伸苯基、^伸苯基或雙紛二價自由(或雙游離基)基 89288.doc 1335926 單位、但較佳是1,3-伸苯基。
本發明的環氧樹脂組合物之此種組份,如PTC專利申請 案03/029258中所述,可由任何的數種途徑製成:(1)RP0C12 與HO-芳基-OH或其鹽類之反應,其中R係低碳烷基,較佳 係甲基;(2)在轉酯化(反應)條件下,烷基膦酸二苯酯,較 佳膦酸甲酯與HO-伸芳基-OH之反應;(3)具有-0P(0R’)-0-伸芳基-結構的重複單元之低聚合亞磷酸鹽與Arbuzov重排 觸媒的反應,其中R'是低碳烷基,較佳係曱基;或(4)具有 -OP(0-Ph)-0-伸芳基結構之重複單元之低聚合亞磷酸鹽連 同亞磷酸三甲酯與Arbuzov觸媒或連同甲基膦酸二甲酯,視 需要與Arbuzov觸媒-之反應。-OH端基(如果附著至伸芳基) 可由具有受控制之莫耳過量的HO-伸芳基-OH在反應介質 中予以產生。-OH端基(如係酸型(P-OH))可由水解反應予以 產生。最好:低聚物的端基主要是伸芳基-OH型。
本發明的環氧樹脂組合物同樣可含有視需要之添加劑包 括下列各型的物質:纖維及/或布增強之添加劑、脫模劑、 著色劑及其類似物。 【實施方式】 實例 物質 環氧-雙酚A型環氧樹脂 線型酚醛樹脂-酚甲醛樹脂(線型酚醛樹脂型)(輔助固化 劑) 三聚氰胺-線型酚醛樹脂-酚、三聚氰胺和甲醛的共聚物(輔 89288.doc 1335926 助固化劑) 磷光體-線型酚醛樹脂-磷酸化之酚-甲醛樹脂(輔助固化 劑) ATH-鋁三水合物 膦酸酯-反應性膦酸酯固化劑,其中π伸芳基”是間苯二酚 DICY-雙氰胺(輔助固化劑) ΑΜΙ-2- 2-甲基咪唑(觸媒)
BDP-雙酚 Α雙(磷酸二苯酯)Akzo Nobel 牌 FYROLFLEX BDP BDP(OH)-如美國專利第3,090,799號中所述予以造成之 雙酚A磷酸二苯酯
RDP(OH)2-如美國專利第5,508,462號中所述予以造成之 間苯二齡'、雙(麟酸苯基resolcinyl酯)
Tg- TMA實驗中所量測之玻璃轉移溫度,如IPC-TM-650 議定書中所述。 UL 94-根據UL 94垂直議定書,可燃性評級(V-0,V-1,V-2) PCT-根據IPC-TM-650議定書,暴露至加壓蒸煮器試驗中之 實驗 89288.doc •10- 1335926 水蒸汽的時間。水吸收係在自熱壓器中取出試樣後予以量測。 剝層-如IPC-TM-650議定書中所述,在260或288°C下, 於TMA實驗中所量測。 CTE-在低於和高於玻璃轉移溫度(各自是<Tg*>Tg)之 溫度下,於TMA實驗中所量測之熱膨脹係數。遵循IPC-TM-650議定書。 下列所複製之表I和II特舉出代表本發明的具體實施例之 許多配方。表III顯示一組的比較性配方。
表I 實例 1 2 3 4 5 6 7 8 組份 環氧,重量% 45 45 40 40 40 40 40 40 線型酚醛樹脂,重量% 10 10 5 5 ATH,重量% 25 25 35 35 35 30 50 50 膦酸酯,重量% 20 20 20 20 25 30 10 9 DICY 1 AMI-2,重量% 0.25 0.5 0.25 0.25 0.1 0.25 0.25 物理性質 Tg5 °c 130 130 110 120 140 110 120 130 UL-94,評級 不合格 不合格 V-1 V-0 不合格 不合格 V-0 V-0 PCT,時間(分)/ 合格(不合格) 60/F 60/F 30/F 60/F 60/F 60/P 30/P 30/F 水吸收,% 0.4 0.4 0.3 0.3 0.1 0.2 0.3 剥層260°C,分 >60 288°C,分 >60 >60 >60 >60 >60 CTE,<TK,106 毫米 50 40 40 30 40 >Te,106 毫米 250 250 200 160 195 89288.doc -11 - 1335926 表II 實例 9 10 11 12 13 14 15 16 組份 環氧,重量% 30 20 20 20 40 35 20 20 線型酚醛樹脂,重量% 10 10 5 5 三聚氰胺-線型酚醛樹 脂,重量% 15 10 10 5 PBZ,重量% 15 15 15 15 15 15 ATH2,重量% 25 35 50 50 25 35 35 50 膦酸酿,重量% 20 20 10 10 20 20 20 10 AMI-2,重量% 0.25 0.25 0.25 0.25 0.25 0.25 0.25 物理性質 Tg, °C 140 150 190 130 120 160 UL-94,評級 不合格 V-1 V-0 V-0 不合格 V-1 V-1 V-0 PCT,時間(分)/ 合格(不合格) 60/P 90/P 90/P 90/F 12Q/P 120/P 90/P 90/F 水吸收,% 0.8 1.2 0.3 0.5 1.0 0.9 1.2 0.2 剝層260°C,分 5 5 288°C,分 >60 >60 >60 CTE,<Tg,106 毫米 30 30 30 40 35 40 >Tg,106 毫米 160 130 160 160 200 165 89288.doc •12- 1335926 表III (比較) 實例 17 18 19 20 21 組份 環氧,重量% 40 35 35 35 35 磷光體-線型酚醛樹脂,重量% 15 10 三聚氰胺-線型酚醛樹脂,重量% 10 10 10 BDP,重量% 20 BDP(OH),重量% 20 RDP(OH)2,重量% 20 膦酸酯,重量% 20 20 ATH,重量% 25 35 35 35 35 AMI-2,重量% 0.25 0.25 0.25 0.25 0.25 物理性質 Tg, °c 100 115 120 120 UL-94,評級 不合格 V-1 不合格 不合格 不合格 PCT,時間(分)/合格(不合格) 60/F 60/F 30/F 60/F 120/P 水吸收,% 0.4 0.4 0.2 0.3 0.6 剝層260°C,分 >60 288。。,分 20 >60 >60 >60 CTE,<Tg,106 毫米 50 50 65 60 〉Tg, 106 毫米 230 240 210 200 89288.doc -13-
Claims (1)
1335926 --------- Ϊ 092131258號專利申請案jf#名月修(更)正木 中文申請專利範圍替換本(99 b月)--___ 拾、申請專利範園: L 一種環氧樹脂組合物’其包括環氧樹脂、具有重複結構 (0)(R)0伸芳基_之反應性經基封端低聚膦酸醋固化 劑,其中R係低碳烧基、無機填料、聚苯并十井樹脂及視 需要之共固化劑。 2.如申請專利範圍第i項之組合物,其中該環氧樹脂包括組 合物總重量的自約10重量%至約5〇重量%。 3·如申請專利範圍第i項之組合物,其中反應性經基封端低 聚膦酸酯固化劑包括組合物總重量的自約5重量%至約% 重量%。 4. 如申凊專利圍第i項之組合物,其中聚苯并十井樹脂包 括組合物總重量的至高約5〇重量0/〇。 5. 如申請專利範圍第i項之組合物,其中共固化劑包括組合 物總重量的自約5重量%至約2 〇重量%。 6. 如申明專利範圍第1項之組合物,其中無機填料包括組合 物總重量的自約1 〇重量%至約5 〇重量%。 7·如申請專利範圍第丨項之組合物,其中該環氧樹脂包括組 合物總重量的自約1〇重量%至約50重量%,該反應性羥基 封端低聚膦酸酯固化劑包括組合物總重量自約5重量%至 約30重量%,該無機填料包括組合物總重量自約1〇重量% 至約50重量%,及苯并嘮畊樹脂包括組合物總重量至高約 50重量%。 8.如申請專利範圍第7項之組合物,另外包括一種共固化劑 其數量是組合物總重量自約5重量%至約2〇重量%。 89288-990302.doc 1335926 9.如申請專利範圍第1至6項和8馆击, 唄和8項中任一組之組合物,苴中 該共固化劑係由下列各化合物所組成之群中選出:線型 酚路樹脂、二聚氰胺-線型㈣樹脂及填光體'線型㈣樹 脂%組合物。 10·如申凊專利範圍第1項之組合物,其中尺係甲基。 U.如中請專利範圍第!項之組合物,其中伸芳基係仏伸苯 基。 12.如申請專利範圍第丨項之組合物,其中伸芳基係雙酚二價 自由基單位。 13 _如申睛專利範圍第1項之組合物’其中伸芳基係雙酚二價 自由基單位及R係甲基。
89288-990302.doc
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ES (2) | ES2273060T3 (zh) |
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CN1723243A (zh) | 2006-01-18 |
EP1570000A1 (en) | 2005-09-07 |
ES2359226T3 (es) | 2011-05-19 |
CN100402605C (zh) | 2008-07-16 |
US20060142427A1 (en) | 2006-06-29 |
ES2273060T3 (es) | 2007-05-01 |
ATE494329T1 (de) | 2011-01-15 |
EP1719802B1 (en) | 2011-01-05 |
DE60308548T2 (de) | 2007-09-20 |
ATE340220T1 (de) | 2006-10-15 |
EP1719802B2 (en) | 2015-11-25 |
WO2004044054A1 (en) | 2004-05-27 |
EP1570000B1 (en) | 2006-09-20 |
EP1719802A1 (en) | 2006-11-08 |
KR101169658B1 (ko) | 2012-08-03 |
TW200417575A (en) | 2004-09-16 |
US7427652B2 (en) | 2008-09-23 |
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DE60308548D1 (de) | 2006-11-02 |
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