TWI335926B - Epoxy resin composition containing reactive phosphonate flame retardant and filler - Google Patents

Epoxy resin composition containing reactive phosphonate flame retardant and filler Download PDF

Info

Publication number
TWI335926B
TWI335926B TW092131258A TW92131258A TWI335926B TW I335926 B TWI335926 B TW I335926B TW 092131258 A TW092131258 A TW 092131258A TW 92131258 A TW92131258 A TW 92131258A TW I335926 B TWI335926 B TW I335926B
Authority
TW
Taiwan
Prior art keywords
composition
weight
curing agent
resin
total weight
Prior art date
Application number
TW092131258A
Other languages
English (en)
Other versions
TW200417575A (en
Inventor
Mark Buczek
Sergei V Levchik
Original Assignee
Supresta Llc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=32312940&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=TWI335926(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Supresta Llc filed Critical Supresta Llc
Publication of TW200417575A publication Critical patent/TW200417575A/zh
Application granted granted Critical
Publication of TWI335926B publication Critical patent/TWI335926B/zh

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/49Phosphorus-containing compounds
    • C08K5/51Phosphorus bound to oxygen
    • C08K5/53Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5317Phosphonic compounds, e.g. R—P(:O)(OR')2
    • C08K5/5333Esters of phosphonic acids
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00Polycondensates 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
    • C08G59/18Macromolecules 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
    • C08G59/40Macromolecules 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
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00Polycondensates 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
    • C08G59/18Macromolecules 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
    • C08G59/40Macromolecules 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
    • C08G59/4007Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4071Curing agents not provided for by the groups C08G59/42 - C08G59/66 phosphorus containing compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00Polycondensates 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
    • C08G59/18Macromolecules 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
    • C08G59/40Macromolecules 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
    • C08G59/62Alcohols or phenols
    • C08G59/621Phenols
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00Use of inorganic substances as compounding ingredients
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/49Phosphorus-containing compounds
    • C08K5/51Phosphorus bound to oxygen
    • C08K5/52Phosphorus bound to oxygen only
    • C08K5/521Esters of phosphoric acids, e.g. of H3PO4
    • C08K5/523Esters of phosphoric acids, e.g. of H3PO4 with hydroxyaryl compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • HELECTRICITY
    • H05ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05KPRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00Printed circuits
    • H05K1/02Details
    • H05K1/03Use of materials for the substrate
    • H05K1/0313Organic insulating material
    • H05K1/0353Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
    • H05K1/0373Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement containing additives, e.g. fillers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/34Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C08L61/04, C08L61/18 and C08L61/20
    • HELECTRICITY
    • H05ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05KPRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K2201/00Indexing scheme relating to printed circuits covered by H05K1/00
    • H05K2201/01Dielectrics
    • H05K2201/0104Properties and characteristics in general
    • H05K2201/012Flame-retardant; Preventing of inflammation
    • HELECTRICITY
    • H05ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05KPRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K2201/00Indexing scheme relating to printed circuits covered by H05K1/00
    • H05K2201/02Fillers; Particles; Fibers; Reinforcement materials
    • H05K2201/0203Fillers and particles
    • H05K2201/0206Materials
    • H05K2201/0209Inorganic, non-metallic particles

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Epoxy Resins (AREA)

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
TW092131258A 2002-11-08 2003-11-07 Epoxy resin composition containing reactive phosphonate flame retardant and filler TWI335926B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US42519602P 2002-11-08 2002-11-08

Publications (2)

Publication Number Publication Date
TW200417575A TW200417575A (en) 2004-09-16
TWI335926B true TWI335926B (en) 2011-01-11

Family

ID=32312940

Family Applications (1)

Application Number Title Priority Date Filing Date
TW092131258A TWI335926B (en) 2002-11-08 2003-11-07 Epoxy resin composition containing reactive phosphonate flame retardant and filler

Country Status (12)

Country Link
US (1) US7427652B2 (zh)
EP (2) EP1570000B1 (zh)
JP (1) JP2006505679A (zh)
KR (1) KR101169658B1 (zh)
CN (1) CN100402605C (zh)
AT (2) ATE494329T1 (zh)
AU (1) AU2003290646A1 (zh)
CA (1) CA2505396A1 (zh)
DE (2) DE60335671D1 (zh)
ES (2) ES2273060T3 (zh)
TW (1) TWI335926B (zh)
WO (1) WO2004044054A1 (zh)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1432719A1 (en) * 2001-10-04 2004-06-30 Akzo Nobel N.V. Oligomeric, hydroxy-terminated phosphonates
EP1625171A1 (en) * 2003-05-22 2006-02-15 Supresta LLC Polyphosphonate flame retardant curing agent for epoxy resin
US7910665B2 (en) 2004-05-19 2011-03-22 Icl-Ip America Inc. Composition of epoxy resin and epoxy-reactive polyphosphonate
TW200916561A (en) * 2007-05-07 2009-04-16 Martinswerk Gmbh Flame retarded thermosets
US9348991B2 (en) * 2008-05-20 2016-05-24 International Business Machines Corporation User management of authentication tokens
TWI423741B (zh) * 2009-02-13 2014-01-11 Iteq Corp An epoxy resin composition and a film and a substrate made of the epoxy resin composition
HUE048499T2 (hu) * 2010-03-05 2020-07-28 Huntsman Advanced Mat Americas Llc Alacsony dielektromos veszteségû hõre keményedõ gyantarendszer nagyfrekvencián elektromos alkatrészekben történõ alkalmazásra
US20120095132A1 (en) * 2010-10-19 2012-04-19 Chung-Hao Chang Halogen- and phosphorus-free thermosetting resin composition
CN103384674B (zh) 2010-12-22 2015-06-10 Frx聚合物股份有限公司 寡聚的膦酸酯及包括所述寡聚的膦酸酯的组合物
CN102408419B (zh) * 2011-08-10 2014-11-05 哈尔滨理工大学 苯并噁嗪树脂的方法
WO2014116669A1 (en) * 2013-01-22 2014-07-31 Frx Polymers, Inc. Phosphorus containing epoxy compounds and compositions therefrom
JP2015040289A (ja) * 2013-08-23 2015-03-02 三菱化学株式会社 エポキシ樹脂、エポキシ樹脂組成物、硬化物及び電気・電子回路用積層板
CN105802127B (zh) * 2014-12-29 2018-05-04 广东生益科技股份有限公司 一种无卤热固性树脂组合物及使用它的预浸料以及印制电路用层压板
CN105802128B (zh) * 2014-12-29 2018-05-04 广东生益科技股份有限公司 一种无卤热固性树脂组合物及使用它的预浸料和印制电路用层压板
CN105801814B (zh) * 2014-12-29 2018-05-04 广东生益科技股份有限公司 一种无卤热固性树脂组合物及使用它的预浸料和印制电路用层压板
CN107151308B (zh) * 2016-03-04 2019-06-14 广东生益科技股份有限公司 一种无卤热固性树脂组合物及使用它的预浸料、印制电路用层压板
CN108117634B (zh) * 2016-11-30 2019-08-27 广东生益科技股份有限公司 一种热固性树脂组合物
CN108117632B (zh) * 2016-11-30 2019-08-23 广东生益科技股份有限公司 一种热固性树脂组合物
CN108164684B (zh) * 2016-12-07 2019-08-27 广东生益科技股份有限公司 一种热固性树脂组合物
RU2749320C1 (ru) 2017-09-13 2021-06-08 Хексион Инк. Системы эпоксидных смол
KR102346010B1 (ko) * 2019-09-19 2021-12-31 코오롱인더스트리 주식회사 말단이 불포화기로 캡핑된 인 함유 수지, 이의 제조방법 및 상기 말단이 불포화기로 캡핑된 인 함유 수지를 포함하는 수지 조성물
CN114539313B (zh) * 2022-02-23 2024-04-26 长春市兆兴新材料技术有限责任公司 一种双反应型膦酸酯交联阻燃剂及其制备方法

Family Cites Families (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2682522A (en) * 1952-09-10 1954-06-29 Eastman Kodak Co Process for preparing polymeric organo-phosphonates
US2716101A (en) * 1952-09-10 1955-08-23 Eastman Kodak Co Polymeric organo-phosphonates containing phosphato groups
FR1438381A (fr) * 1964-03-28 1966-05-13 Gelsenberg Benzin Ag Procédé de préparation de phosphonates contenant des groupes hydroxyle
GB1308521A (en) * 1970-03-23 1973-02-21 Exxon Research Engineering Co Phenolic stabilizers and compositions containing them
SU1153835A3 (en) 1973-09-11 1985-04-30 Sumitomo Bakelite Co Binder for laminated plastics
DE2715589A1 (de) * 1976-04-14 1977-10-27 Ciba Geigy Ag Neue phenol-stabilisatoren
US4268633A (en) * 1978-04-20 1981-05-19 Stauffer Chemical Company Polyurethanes containing a poly (oxyorganophosphate/phosphonate) flame retardant
DE2925207A1 (de) * 1979-06-22 1981-01-29 Bayer Ag Thermoplastische, verzweigte, aromatische polyphosphonate, ihre verwendung und ein verfahren zu ihrer herstellung
DE3139958A1 (de) * 1981-10-08 1983-04-28 Basf Ag, 6700 Ludwigshafen Selbstverloeschende thermoplastische formmassen
DE3520296A1 (de) * 1985-06-07 1986-12-11 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von copolyphosphonaten mit hoher zaehigkeit
DE3800672A1 (de) * 1988-01-13 1989-07-27 Bayer Ag Flammgeschuetzte polyethylenterephthalatformmassen
DE3833694A1 (de) * 1988-10-04 1990-04-05 Bayer Ag Flammgeschuetzte, gut kristallisierende polyethylenterephthalatformmassen
US4952646A (en) 1989-07-20 1990-08-28 Akzo America Inc. Epoxy resin compositions containing a polyphosphoric/polyphosphonic anhydride curing agent
FR2660302B1 (fr) * 1990-03-30 1992-08-07 Selas Sa Installation pour le chauffage, le formage et la trempe de feuilles de verre.
GB9007515D0 (en) * 1990-04-03 1990-05-30 Ciba Geigy Ag Products
US6005064A (en) * 1993-12-27 1999-12-21 Hitachi Chemical Company, Ltd. Thermosetting compounds, cured product thereof and method of preparing the thermosetting compound
JPH08183835A (ja) 1994-12-28 1996-07-16 Hitachi Chem Co Ltd 熱硬化性樹脂組成物、接着剤シート及び接着剤付き 金属はく
US6214455B1 (en) * 1995-09-29 2001-04-10 Toshiba Chemical Corporation Bisphenol A and novolak epoxy resins with nitrogen-containing phenolic resin
JP3487083B2 (ja) * 1996-02-09 2004-01-13 日立化成工業株式会社 熱硬化性樹脂組成物及びその硬化物
GB9713526D0 (en) * 1997-06-26 1997-09-03 Dow Deutschland Inc Flame retardant laminating formulations
US6353080B1 (en) 1997-06-26 2002-03-05 The Dow Chemical Company Flame retardant epoxy resin composition
JPH1180178A (ja) * 1997-09-12 1999-03-26 Hitachi Chem Co Ltd リン含有フェノール末端オリゴマー及びその製造法
JP2000226499A (ja) * 1998-12-03 2000-08-15 Hitachi Chem Co Ltd 封止用エポキシ樹脂成形材料及び電子部品装置
JP2000256633A (ja) 1999-03-09 2000-09-19 Hitachi Chem Co Ltd 接着剤組成物
JP4353589B2 (ja) * 1999-07-09 2009-10-28 株式会社Adeka 難燃性エポキシ樹脂組成物
JP2001098273A (ja) * 1999-09-30 2001-04-10 Nippon Chem Ind Co Ltd 難燃剤組成物および難燃性樹脂組成物
JP2001122948A (ja) * 1999-10-28 2001-05-08 Hitachi Chem Co Ltd 難燃性樹脂組成物、プリプレグ及びプリント配線板用積層板
TW587094B (en) 2000-01-17 2004-05-11 Sumitomo Bakelite Co Flame-retardant resin composition comprising no halogen-containing flame retardant, and prepregs and laminates using such composition
US6440567B1 (en) * 2000-03-31 2002-08-27 Isola Laminate Systems Corp. Halogen free flame retardant adhesive resin coated composite
JP2001302879A (ja) * 2000-04-25 2001-10-31 Shin Kobe Electric Mach Co Ltd エポキシ樹脂組成物、ならびにそれを用いたプリプレグおよびプリント配線板
JP2002088138A (ja) * 2000-09-14 2002-03-27 Asahi Denka Kogyo Kk エポキシ樹脂組成物
MY142518A (en) 2001-01-10 2010-12-15 Hitachi Chemical Co Ltd Dihydrobenzoxazine ring-containing resin, phenolic-triazine-aldehyde condensate and epoxy resin
MY138485A (en) 2001-03-12 2009-06-30 Hitachi Chemical Co Ltd Process for producing benzoxazine resin
EP1432719A1 (en) * 2001-10-04 2004-06-30 Akzo Nobel N.V. Oligomeric, hydroxy-terminated phosphonates

Also Published As

Publication number Publication date
US20060142427A1 (en) 2006-06-29
EP1719802A1 (en) 2006-11-08
EP1719802B2 (en) 2015-11-25
ES2359226T3 (es) 2011-05-19
ATE340220T1 (de) 2006-10-15
EP1570000A1 (en) 2005-09-07
AU2003290646A1 (en) 2004-06-03
WO2004044054A1 (en) 2004-05-27
ES2273060T3 (es) 2007-05-01
CN1723243A (zh) 2006-01-18
CA2505396A1 (en) 2004-05-27
DE60335671D1 (de) 2011-02-17
JP2006505679A (ja) 2006-02-16
KR101169658B1 (ko) 2012-08-03
CN100402605C (zh) 2008-07-16
ATE494329T1 (de) 2011-01-15
TW200417575A (en) 2004-09-16
US7427652B2 (en) 2008-09-23
DE60308548D1 (de) 2006-11-02
KR20050087793A (ko) 2005-08-31
EP1719802B1 (en) 2011-01-05
DE60308548T2 (de) 2007-09-20
EP1570000B1 (en) 2006-09-20

Similar Documents

Publication Publication Date Title
TWI335926B (en) Epoxy resin composition containing reactive phosphonate flame retardant and filler
CN105238000A (zh) 一种低介电复合材料及其积层板和电路板
CN105440645A (zh) 含磷阻燃剂的低介电树脂组合物及其制备方法和应用
JP6063521B2 (ja) リン含有フェノール樹脂化合物及びそれを原料として調製されたリン含有難燃性エポキシ樹脂硬化物
JP2008179819A (ja) 難燃性樹脂組成物、それを用いたプリプレグ、積層板、金属張積層板、印刷配線板及び多層印刷配線板
JP3588456B2 (ja) 窒素を含む難燃性エポキシ樹脂とその組成物
JP2960897B2 (ja) エポキシ樹脂、リン含有化合物および硬化剤を含有するリン変性エポキシ樹脂組成物
US20150189745A1 (en) Epoxy resin composition, and, prepreg and copper clad laminate manufactured using the composition
CN109082118A (zh) 一种树脂组合物及其制品
TW201132700A (en) Compositions having phosphorus-containing compounds
CN108456397A (zh) 具有低介电损耗的无卤素环氧树脂组成物
CA2266903A1 (en) Epoxy resin mixtures
KR101909314B1 (ko) 에폭시 수지 경화 억제제로서의 알루미늄 아인산염
JP3664124B2 (ja) 難燃性樹脂組成物、それを用いたプリプレグ、積層板、金属張積層板、印刷配線板及び多層印刷配線板
JPH09104804A (ja) 耐炎性エポキシ樹脂成形材料
JP3484403B2 (ja) リン含有難燃性エポキシレジン、およびその製造方法
TWI617614B (zh) Epoxy resin composition and prepreg and copper clad laminate prepared using same
JP2661109B2 (ja) 難燃性フェノール樹脂組成物
JP5024605B2 (ja) 硬化性樹脂組成物、その硬化物、新規フェノール樹脂及びその製造方法
JP2005036242A (ja) 難燃性樹脂組成物、それを用いたプリプレグ、積層板、金属張積層板、印刷配線板及び多層印刷配線板
JP2006045546A (ja) 熱硬化性樹脂組成物、ホウ酸変性トリアジン構造含有ノボラック樹脂、およびその製造方法
JP3423170B2 (ja) 熱硬化性樹脂組成物
US20110065870A1 (en) Tris(Hydroxoxyphenyl) Phosphine Oxides and their Use as Flame Retardants for Epoxy Resins
JP2016020445A (ja) エポキシ樹脂組成物、硬化物、繊維強化複合材料、繊維強化樹脂成形品、半導体封止材料、半導体装置、プリプレグ、回路基板、ビルドアップフィルム、及びビルドアップ基板
JPH0125495B2 (zh)

Legal Events

Date Code Title Description
GD4A Issue of patent certificate for granted invention patent
MM4A Annulment or lapse of patent due to non-payment of fees