JP2000281997A - Thermally conductive, flame-retardant pressure- sensitive adhesive and pressure-sensitive adhesive tape - Google Patents
Thermally conductive, flame-retardant pressure- sensitive adhesive and pressure-sensitive adhesive tapeInfo
- Publication number
- JP2000281997A JP2000281997A JP11088142A JP8814299A JP2000281997A JP 2000281997 A JP2000281997 A JP 2000281997A JP 11088142 A JP11088142 A JP 11088142A JP 8814299 A JP8814299 A JP 8814299A JP 2000281997 A JP2000281997 A JP 2000281997A
- Authority
- JP
- Japan
- Prior art keywords
- sensitive adhesive
- pressure
- flame
- electrically insulating
- heat
- Prior art date
- Legal status (The legal status 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 status listed.)
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Links
Landscapes
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、熱伝導電気絶縁性
充填剤と含窒素リン化合物を含有した熱伝導難燃性感圧
接着剤及び感圧接着テープ類に関する。本発明の感圧接
着剤及び感圧接着テープ類は、優れた接着性と電気絶縁
性、熱伝導性、難燃性を併せ持ち、電子部品の固定、特
に電子部品とヒートシンクの接着固定、車両、航空機、
船舶等の各分野での部材の固定用途に有用である。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a heat-conductive flame-retardant pressure-sensitive adhesive and a pressure-sensitive adhesive tape containing a heat-conductive electrically insulating filler and a nitrogen-containing phosphorus compound. The pressure-sensitive adhesive and the pressure-sensitive adhesive tapes of the present invention have excellent adhesiveness and electrical insulation, heat conductivity, and flame retardancy, and fix electronic components, particularly, fix and fix electronic components and heat sinks, vehicles, aircraft,
It is useful for fixing members in various fields such as ships.
【０００２】[0002]
【従来の技術】近年、エレクトロニクス技術の格段なる
進歩により電気、電子機器の高集積化・高性能化が進む
に伴い、半導体やパワートランジスター等の電子部品の
発熱量の増加による機能異常が発生している。機能異常
を防止するため、電子部品にヒートシンクを接着又は機
械的に固定して熱放散を行っている。この接合部材には
熱伝導性と電気絶縁性が同時に要求される。また、熱が
蓄積した場合においても、発火の危険性が無いように接
着部材には高い難燃性が要求される。しかし、ＵＳＰ．
４，５７４，８７９号（ＤｅＧｒｅｅら）に記載されて
いる機械的な固定方法は、良好な熱伝導性、難燃性を有
するが、部品の固定に数段階の工程を有し、特に電子部
品が小さくなるに従って時間を要する。特開平６−８８
０６１に記載されている、熱伝導電気絶縁粒子をランダ
ムに分散した熱伝導電気絶縁感圧接着剤は、熱伝導性と
電気絶縁性、接着性を併せ持つものの、難燃性に関する
記載は無く、実際に燃焼するためＵＬ−９４試験に合格
しない。2. Description of the Related Art In recent years, with the remarkable progress in electronics technology, the integration of electric and electronic devices has become higher and higher in performance. As a result, malfunctions have occurred due to an increase in the amount of heat generated by electronic components such as semiconductors and power transistors. ing. In order to prevent functional abnormalities, heat dissipation is performed by bonding or mechanically fixing a heat sink to the electronic component. This joint member is required to have thermal conductivity and electrical insulation at the same time. Further, even when heat is accumulated, the adhesive member is required to have high flame retardancy so that there is no risk of ignition. However, USP.
The mechanical fixing method described in US Pat. No. 4,574,879 (DeGree et al.) Has good thermal conductivity and flame retardancy, but has several steps of fixing parts, especially electronic parts. It takes time as the size becomes smaller. JP-A-6-88
No. 061, the heat conductive electric insulating pressure-sensitive adhesive in which the heat conductive electric insulating particles are randomly dispersed has both heat conductivity, electric insulation, and adhesiveness, but there is no description about flame retardancy. Does not pass the UL-94 test.
【０００３】[0003]
【発明が解決しようとする課題】本発明の課題は、電気
絶縁性と熱伝導性、高接着力を発揮するとともに、更
に、難燃性を併せ持つ感圧接着剤及び感圧接着テープ類
を提供することにある。SUMMARY OF THE INVENTION It is an object of the present invention to provide a pressure-sensitive adhesive and a pressure-sensitive adhesive tape exhibiting electrical insulation, thermal conductivity and high adhesive strength, and further having flame retardancy. Is to do.
【０００４】[0004]
【課題を解決するための手段】本発明者らは鋭意検討の
結果、（メタ）アクリル系共重合体と熱伝導電気絶縁性
充填剤、含窒素リン化合物を特定の配合で添加した感圧
接着剤及び感圧接着テープ類が、電気絶縁性と熱伝導
性、難燃性、高い接着性を併せ持ち、ハロゲン系の難燃
剤や発ガン性の問題がある三酸化アンチモンを一切含有
しないため、ハロゲン系の有毒ガスや煙が発生せず安全
性が高いことを見い出し本発明を完成するに至った。Means for Solving the Problems The inventors of the present invention have conducted intensive studies and have found that a (meth) acrylic copolymer, a heat conductive and electrically insulating filler, and a nitrogen-containing phosphorus compound are added in a specific composition. Since the adhesive and pressure-sensitive adhesive tapes have both electrical insulation, thermal conductivity, flame retardancy, and high adhesiveness and do not contain any halogen-based flame retardants or antimony trioxide, which has carcinogenic properties, halogen The present inventors have found that the system has high safety without generating toxic gas or smoke, and have completed the present invention.
【０００５】即ち、本発明の第一の構成は、（メタ）ア
クリル酸アルキルエステル系モノマーからなる共重合体
１００重量部（以下／部）と、熱伝導電気絶縁性充填剤
と含窒素リン化合物の比率が８：２〜３：７で総量が５
０〜２００部を含有し、熱伝導率が０．３Ｗ／ｍ・Ｋ以
上であることを特徴とする電気絶縁性の熱伝導難燃性感
圧接着剤に関する。That is, a first constitution of the present invention is to provide a copolymer comprising an alkyl (meth) acrylate ester monomer of 100 parts by weight (hereinafter referred to as "part / part"), a heat conductive and electrically insulating filler and a nitrogen-containing phosphorus compound. Is 8: 2 to 3: 7 and the total amount is 5
The present invention relates to an electrically insulating, heat-conductive, flame-retardant, pressure-sensitive adhesive containing 0 to 200 parts and having a thermal conductivity of 0.3 W / m · K or more.
【０００６】本発明はまた熱伝導電気絶縁性充填剤が金
属酸化物、金属窒化物及び、水和金属化合物からなる群
から選ばれる１種以上であり、更に水和金属化合物が水
酸化アルミニウムであり、含窒素リン化合物がポリリン
酸アンモニウムである前記した電気絶縁性の熱伝導難燃
性感圧接着剤に関する。In the present invention, the heat conductive and electrically insulating filler is at least one selected from the group consisting of metal oxides, metal nitrides and hydrated metal compounds, and the hydrated metal compound is aluminum hydroxide. The present invention relates to the above-mentioned electrically insulating heat-conductive flame-retardant pressure-sensitive adhesive, wherein the nitrogen-containing phosphorus compound is ammonium polyphosphate.
【０００７】本発明はまた含窒素リン化合物の難燃助剤
として脂肪族多価アルコール及び／又は脂肪族多価アル
コールの誘導体を含有し、更に脂肪族多価アルコール誘
導体がロジン系樹脂と脂肪族多価アルコールのエステル
化物である前記した電気絶縁性の熱伝導難燃性感圧接着
剤に関する。The present invention also contains an aliphatic polyhydric alcohol and / or a derivative of an aliphatic polyhydric alcohol as a flame-retardant auxiliary for a nitrogen-containing phosphorus compound, and the aliphatic polyhydric alcohol derivative further comprises a rosin resin and an aliphatic polyhydric alcohol derivative. The present invention relates to the above-mentioned electrically insulating heat-conductive flame-retardant pressure-sensitive adhesive which is an esterified product of a polyhydric alcohol.
【０００８】本発明はまた、（メタ）アクリル酸アルキ
ルエステル系モノマーを光重合して得られた共重合体で
ある前記した電気絶縁性の熱伝導難燃性感圧接着剤に関
する。[0008] The present invention also relates to the above-mentioned electrically insulating, heat-conductive, flame-retardant, pressure-sensitive adhesive, which is a copolymer obtained by photopolymerizing an alkyl (meth) acrylate monomer.
【０００９】本発明の第二の構成は、基材の少なくとも
一面に前記した電気絶縁性の熱伝導難燃性感圧接着剤を
設けた熱伝導率が０．３Ｗ／ｍ・Ｋ以上であることを特
徴とする感圧接着テープ類に関する。[0009] A second configuration of the present invention is that the above-described electrically insulating heat-conductive and flame-retardant pressure-sensitive adhesive is provided on at least one surface of the base material and has a thermal conductivity of 0.3 W / m · K or more. Pressure-sensitive adhesive tapes characterized by the following.
【００１０】[0010]
【発明の実施の形態】本発明に於いて用いられる（メ
タ）アクリル酸アルキルエステル系モノマーからなる共
重合体としては、特に限定されないが、例としては、ア
クリル酸エチル、アクリル酸プロピル、アクリル酸ブチ
ル、アクリル酸イソブチル、アクリル酸イソアミル、ア
クリル酸ヘキシル、アクリル酸オクチル、アクリル酸イ
ソノリル、アクリル酸イソデシル、メタクリル酸ブチ
ル、メタクリル酸ヘキシル、メタクリル酸イソデシル、
メタクリル酸ラウリル等を主成分とするものが挙げられ
る。接着性を向上するためにアクリル酸やＮ−ビニルピ
ロリドン等の極性ビニルモノマーを共重合することもで
きる。BEST MODE FOR CARRYING OUT THE INVENTION The copolymer comprising an alkyl (meth) acrylate monomer used in the present invention is not particularly limited, but examples thereof include ethyl acrylate, propyl acrylate, and acrylic acid. Butyl, isobutyl acrylate, isoamyl acrylate, hexyl acrylate, octyl acrylate, isonolyl acrylate, isodecyl acrylate, butyl methacrylate, hexyl methacrylate, isodecyl methacrylate,
Those containing lauryl methacrylate or the like as a main component are exemplified. A polar vinyl monomer such as acrylic acid or N-vinylpyrrolidone can be copolymerized to improve the adhesiveness.
【００１１】また感圧接着剤を架橋するために、ヒドロ
キシエチル（メタ）アクリレート、４ヒドロキシブチル
アクリレート等の水酸基含有モノマーを添加してもよ
い。In order to crosslink the pressure-sensitive adhesive, a hydroxyl group-containing monomer such as hydroxyethyl (meth) acrylate or 4-hydroxybutyl acrylate may be added.
【００１２】上記アクリル系共重合体の重合方法として
は、例えば溶液重合、隗状重合、懸濁重合、乳化重合、
ＵＶ重合等の公知の重合方法で共重合させることにより
得ることが出来る。重合開始方法も、過酸化ベンゾイル
や過酸化ラウロイル等の過酸化物系、アゾビスイソブチ
ルニトリル等のアゾ系の熱重合開始剤を用いた熱による
開始方法や、アセトフェノン系、ベンゾインエーテル
系、ベンジルケタール系、アシルフォスフィンオキサイ
ド系、ベンゾイン系、ベンゾフェノン系の光重合開始剤
を用いた低強度の紫外線照射による開始方法や、電子線
照射による方法を任意に選択できる。The polymerization method of the acrylic copolymer includes, for example, solution polymerization, bulk polymerization, suspension polymerization, emulsion polymerization,
It can be obtained by copolymerization by a known polymerization method such as UV polymerization. The polymerization initiation method is also a thermal initiation method using a thermal polymerization initiator such as a peroxide system such as benzoyl peroxide or lauroyl peroxide or an azo system such as azobisisobutylnitrile, or an acetophenone system, a benzoin ether system or a benzyl ketal. A method of starting by low-intensity ultraviolet irradiation using a photopolymerization initiator of a system, acylphosphine oxide system, benzoin system, or benzophenone system or a method by electron beam irradiation can be arbitrarily selected.
【００１３】本発明に使用される感圧接着剤の凝集力の
向上のため適宜架橋してもよい。架橋剤としては、（メ
タ）アクリル系モノマーを重合する際に多官能（メタ）
アクリレートを添加するか、共重合体を製造した後にエ
ポキシ系架橋剤、イソシアネート系架橋剤、アジリジン
系架橋剤、キレート系架橋剤を用いることができる。The pressure-sensitive adhesive used in the present invention may be appropriately cross-linked to improve cohesion. As a cross-linking agent, a polyfunctional (meth)
After adding an acrylate or producing a copolymer, an epoxy-based crosslinking agent, an isocyanate-based crosslinking agent, an aziridine-based crosslinking agent, or a chelating-based crosslinking agent can be used.
【００１４】また接着性を向上させるために、必要に応
じ粘着付与樹脂を添加しても良い。Further, in order to improve the adhesiveness, a tackifier resin may be added as required.
【００１５】本発明で使用する熱伝導電気絶縁性充填剤
とは、熱伝導性が高く、電気的に絶縁性である充填材で
あり、特に限定されないが、例えば金属酸化物、金属窒
化物、水和金属化合物の群から選ばれる。金属酸化物と
しては、酸化アルミ、窒化アルミ等が挙げられる。金属
窒化物としては窒化硼素、窒化アルミ等が挙げられる。
水和金属化合物としては、水酸化アルミニウム、水酸化
マグネシウム等が挙げられる。また（メタ）アクリル系
共重合体への分散性や耐水性を向上するためカップリン
グ処理、ステアリン酸処理、樹脂被服処理、シリカ被服
処理等の表面処理を適宜行っても良い。これらの化合物
粉末の平均粒径は約０．５〜２００μｍ、好ましくは１
〜３０μｍである。粒子形状は、球状、針状、フレーク
状が挙げられる。化合物種類及び平均粒径、形状は単独
で使用しても２種以上組み合わせて使用してもよい。The heat conductive and electrically insulating filler used in the present invention is a filler having high heat conductivity and being electrically insulating, and is not particularly limited. Examples thereof include metal oxides, metal nitrides, and the like. It is selected from the group of hydrated metal compounds. Examples of the metal oxide include aluminum oxide and aluminum nitride. Examples of the metal nitride include boron nitride and aluminum nitride.
Examples of the hydrated metal compound include aluminum hydroxide and magnesium hydroxide. Surface treatments such as coupling treatment, stearic acid treatment, resin coating treatment, and silica coating treatment may be appropriately performed in order to improve dispersibility and water resistance in the (meth) acrylic copolymer. The average particle size of these compound powders is about 0.5 to 200 μm, preferably 1 to 200 μm.
３０30 μm. The particle shape includes a spherical shape, a needle shape, and a flake shape. The compound type, the average particle size, and the shape may be used alone or in combination of two or more.
【００１６】本発明で使用する含窒素リン化合物として
は、ポリリン酸アンモニウム、メラミン変性ポリリン酸
アンモニウム、リン酸メラミン、ピロリン酸メラミン等
が挙げられる。また耐水性を向上するために熱硬化性樹
脂で被服もしくはマイクロカプセル等の表面処理を適宜
行っても良い。これらの化合物粉末の平均粒径は約１〜
１００μｍ、好ましくは３〜３０μｍである。化合物の
種類及び平均粒径は単独で使用しても２種以上組み合わ
せて使用しても良い。Examples of the nitrogen-containing phosphorus compound used in the present invention include ammonium polyphosphate, melamine-modified ammonium polyphosphate, melamine phosphate, and melamine pyrophosphate. Further, in order to improve the water resistance, the surface treatment of the coating or the microcapsule with a thermosetting resin may be appropriately performed. The average particle size of these compound powders is about 1 to
It is 100 μm, preferably 3 to 30 μm. The type and average particle size of the compounds may be used alone or in combination of two or more.
【００１７】熱伝導電気絶縁性充填剤と含窒素リン化合
物との比率は、重量比で８：２〜３：７の割合で熱伝導
性と難燃性が両立できるが、６：４〜４：６の比率が好
ましい。熱伝導絶縁性充填剤と含窒素リン化合物の総添
加量としては、（メタ）アクリル酸アルキルエステル系
モノマーからなる共重合体１００部に対し５０〜２００
部である。５０部未満であると熱伝導性、難燃性が極端
に悪化し、２００部を越えると感圧接着性が消失してし
まう。The ratio of the heat conductive electrically insulating filler to the nitrogen-containing phosphorus compound is 8: 2 to 3: 7 by weight, and both heat conductivity and flame retardancy can be obtained. : 6 is preferred. The total amount of the thermally conductive insulating filler and the nitrogen-containing phosphorus compound is from 50 to 200 per 100 parts of the copolymer composed of the alkyl (meth) acrylate monomer.
Department. If the amount is less than 50 parts, the heat conductivity and the flame retardancy are extremely deteriorated, and if it exceeds 200 parts, the pressure-sensitive adhesive property is lost.
【００１８】難燃性を向上するための難燃助剤として難
燃効果を高めるものであれば特に限定されないが、好ま
しくは脂肪族多価アルコールとしては、ペンタエリスリ
トール、ジペンタエリスリトール等が挙げられる。また
脂肪族多価アルコール誘導体としては、ロジン系樹脂と
脂肪族多価アルコールのエステル化物が挙げられる。The flame-retardant auxiliary agent for improving the flame retardancy is not particularly limited as long as it enhances the flame-retardant effect. Preferably, examples of the aliphatic polyhydric alcohol include pentaerythritol and dipentaerythritol. . Examples of the aliphatic polyhydric alcohol derivative include an esterified product of a rosin resin and an aliphatic polyhydric alcohol.
【００１９】本発明で使用する熱伝導電気絶縁性充填剤
と含窒素リン化合物、難燃助剤、架橋剤を感圧接着剤組
成物中に添加し、高速分散機で撹拌分散することにより
熱伝導電気絶縁難燃性感圧接着剤が得られる。The heat-conductive and electrically-insulating filler, the nitrogen-containing phosphorus compound, the flame retardant aid, and the crosslinking agent used in the present invention are added to the pressure-sensitive adhesive composition, and the mixture is stirred and dispersed by a high-speed dispersing machine. A conductive, electrically insulating, flame-retardant pressure-sensitive adhesive is obtained.
【００２０】本発明で使用する基材としては特に限定さ
れないが、好ましくは熱伝導性を向上するためにアル
ミ、銅、鉄等の金属箔や、熱伝導性充填剤を分散したポ
リイミドフィルム等の耐熱フィルムが用いられる。The substrate used in the present invention is not particularly limited, but is preferably a metal foil such as aluminum, copper, iron or the like for improving thermal conductivity, or a polyimide film in which a thermally conductive filler is dispersed. A heat-resistant film is used.
【００２１】[0021]
【実施例】以下に実施例について具体的説明するが、こ
れに限定されるものではない。The present invention will be described in detail with reference to the following Examples, but it should not be construed that the invention is limited thereto.
【００２２】（１−１）（メタ）アクリル系共重合体Ａ
の調整 冷却管、撹拌機、温度計、摘下漏斗を備えた反応容器に
２−エチルヘキシルアクリレート５０部、ｎ−ブチルア
クリレート４６部、アクリル酸４部と重合開始剤として
２，２’−アゾビスイソブチロニトリル０．２部とを酢
酸エチル１００部に溶解し、窒素置換後、８０℃で８時
間重合して固形分５０％、Ｍｗ４０万のアクリル共重合
体溶液を得た。(1-1) (meth) acrylic copolymer A
Preparation of a reaction vessel equipped with a cooling tube, a stirrer, a thermometer, and a dropping funnel, 50 parts of 2-ethylhexyl acrylate, 46 parts of n-butyl acrylate, 4 parts of acrylic acid, and 2,2′-azobis as a polymerization initiator. After dissolving 0.2 part of isobutyronitrile in 100 parts of ethyl acetate, purging with nitrogen and polymerizing at 80 ° C. for 8 hours, an acrylic copolymer solution having a solid content of 50% and Mw of 400,000 was obtained.
【００２３】（１−２）電気絶縁性の熱伝導難燃性感圧
接着剤の調整 （１−１）で得られたアクリル系共重合体溶液に表１の
組み合わせで熱伝導電気絶縁性粒子、含窒素リン化合
物、難燃助剤、トルエンを添加混合し固形分６０％の感
圧接着剤溶液を得た。同表１の配合で架橋剤を添加し均
一になるまで充分撹拌し、電気絶縁性の熱伝導難燃性感
圧接着剤を得た。表１の熱伝導性電気絶縁充填剤におい
て、水和金属化合物は水酸化アルミニウム（昭和電工社
製ハイジライトＨ３２）、金属酸化物は酸化アルミニウ
ム（昭和電工社製アルミナＡＳ５０）、金属窒化物は窒
化アルミニウム（東洋アルミニウム社製ＵＭ）、含窒素
リン化合物としては、ポリリン酸アンモニウム（チッソ
社製テラージュＣ６０）、難燃助剤において、脂肪族多
価アルコールとしてはジペンタエリスリトール（広栄化
学工業社製ジペンタリット）、脂肪族多価アルコール誘
導体としては重合ロジンペンタエリスリトールエステル
（荒川化学社製Ｄ−１３５）、架橋剤はエポキシ系架橋
剤（綜研化学社製Ｅ−０５Ｘ、固形分０．５％）を使用
した。(1-2) Preparation of Electrically Insulating Heat-Conducting Flame-Retardant Pressure-Sensitive Adhesive Heat-Conducting Electrically Insulating Particles in Combination of Table 1 with Acrylic Copolymer Solution Obtained in (1-1) A nitrogen-containing phosphorus compound, a flame retardant aid, and toluene were added and mixed to obtain a pressure-sensitive adhesive solution having a solid content of 60%. The crosslinking agent was added in the composition shown in Table 1 and sufficiently stirred until the mixture became uniform to obtain an electrically insulating heat-conductive flame-retardant pressure-sensitive adhesive. In the heat conductive electric insulating filler shown in Table 1, the hydrated metal compound was aluminum hydroxide (Hijirite H32 manufactured by Showa Denko KK), the metal oxide was aluminum oxide (Alumina AS50 manufactured by Showa Denko KK), and the metal nitride was nitrided. Aluminum (UM manufactured by Toyo Aluminum Co., Ltd.), ammonium polyphosphate (Terage C60 manufactured by Chisso) as a nitrogen-containing phosphorus compound, and dipentaerythritol (Dipentalit manufactured by Koei Chemical Industry Co., Ltd.) as an aliphatic polyhydric alcohol in a flame retardant aid. ), Polymerized rosin pentaerythritol ester (D-135 manufactured by Arakawa Chemical Co., Ltd.) as the aliphatic polyhydric alcohol derivative, and an epoxy-based cross-linking agent (E-05X manufactured by Soken Chemical Co., 0.5% solid content) as the cross-linking agent did.
【００２４】（１−３）テープの調整 （１−２）で得られた電気絶縁性の熱伝導難燃性感圧接
着剤を、乾燥後の厚みが５０μｍになるように、熱伝導
性ポリイミドフィルム（トーレデュポン社製１００Ｍ
Ｔ、厚み２５μｍ、熱伝導性０．４５Ｗ／ｍＫ）の両面
に塗工後、８０℃で５分乾燥し４０℃３日熟成し両面感
圧接着テープを得た。(1-3) Preparation of Tape The heat-conductive polyimide film is prepared by applying the heat-insulating, heat-conductive, flame-retardant pressure-sensitive adhesive obtained in (1-2) to a thickness of 50 μm after drying. (100M made by Torre Dupont)
T, a thickness of 25 μm, and a thermal conductivity of 0.45 W / mK), followed by drying at 80 ° C. for 5 minutes and aging at 40 ° C. for 3 days to obtain a double-sided pressure-sensitive adhesive tape.
【００２５】（２−１）（メタ）アクリル系重合体Ｂの
調整（光重合） 冷却管、撹拌機、温度計、摘下漏斗を備えた反応容器に
イソオクチルアクリレート９５部、アクリル酸５部と光
重合開始剤としてアシルホスフィンオキサイド（ＢＡＳ
Ｆ社製ルシリンＴＰＯ）を０．１部を撹拌混合し窒素置
換後、ケミカルランプを０．５ｍＷ／ｃｍ２ の照射強
度で照射し、重合率３％、粘度１０００ｃｐｓのアクリ
ル部分重合体を得た。(2-1) Preparation of (meth) acrylic polymer B (photopolymerization) In a reaction vessel equipped with a cooling pipe, a stirrer, a thermometer, and a dropping funnel, 95 parts of isooctyl acrylate, 5 parts of acrylic acid And acylphosphine oxide (BAS) as a photopolymerization initiator
0.1 part of Lucilin TPO (manufactured by F Company) was stirred and mixed, and the atmosphere was replaced with nitrogen. Then, the mixture was irradiated with a chemical lamp at an irradiation intensity of 0.5 mW / cm 2 to obtain an acrylic partial polymer having a polymerization rate of 3% and a viscosity of 1000 cps.
【００２６】（２−２）電気絶縁性の熱伝導難燃性感圧
接着剤の調整（光重合） （２−１）で得られたアクリル部分重合体Ｂ１００部に
光開始剤０．１部、光架橋剤０．３部を添加し均一に撹
拌した後、表１の組み合わせで熱伝導電気絶縁性粒子、
含窒素リン化合物、難燃助剤を添加し均一になるまで充
分撹拌した。真空脱泡し電気絶縁性の熱伝導難燃性感圧
接着剤組成物を得た。(2-2) Preparation of Electrically Insulating Heat-Conducting Flame-Retardant Pressure-Sensitive Adhesive (Photopolymerization) 0.1 part of a photoinitiator was added to 100 parts of the acrylic partial polymer B obtained in (2-1). After adding 0.3 part of the photo-crosslinking agent and stirring uniformly, the heat conductive and electrically insulating particles were combined in the combination shown in Table 1,
A nitrogen-containing phosphorus compound and a flame retardant auxiliary were added, and the mixture was sufficiently stirred until it became uniform. Vacuum defoaming was performed to obtain an electrically insulating heat-conductive flame-retardant pressure-sensitive adhesive composition.
【００２７】（２−３）テープの調整（光重合） （２−２）で得られた光重合性の電気絶縁性の熱伝導難
燃性感圧接着剤を、熱伝導性ポリイミドフィルム（トー
レデュポン社製１００ＭＴ、厚み２５μｍ、熱伝導性
０．４５Ｗ／ｍｋ）の両面に重合後の厚みが５０μｍに
なるようにそれぞれ塗工し、重合を阻害する酸素を除去
するために、剥離処理した３８μｍポリエステルフィル
ムで覆い、両面から照射強度１ｍＷ／ｃｍ２になるよう
にケミカルランプで５分間照射し、電気絶縁性の熱伝導
難燃性感圧接着テープを得た。(2-3) Preparation of Tape (Photopolymerization) The photopolymerizable, electrically insulating, heat-conductive, flame-retardant, pressure-sensitive adhesive obtained in (2-2) is applied to a heat-conductive polyimide film (Tore Dupont). Polyester 100MT, thickness 25μm, thermal conductivity 0.45W / mk) Coated on both sides so that the thickness after polymerization is 50μm, and peeled 38μm polyester to remove oxygen which inhibits polymerization The film was covered with a film and irradiated with a chemical lamp for 5 minutes so that the irradiation intensity became 1 mW / cm2 from both sides to obtain an electrically insulating heat-conductive flame-retardant pressure-sensitive adhesive tape.
【００２８】表１の配合で、実施例、比較例として作成
したテープサンプルついて、以下に示す方法により、
〔熱伝導性（率）〕、〔難燃性ＵＬ９４試験〕、〔接着
力〕、〔耐熱保持力〕、〔体積固有抵抗値〕を測定し、
評価結果を表２、３に記した。The tape samples prepared as Examples and Comparative Examples having the composition shown in Table 1 were prepared by the following method.
[Thermal conductivity (rate)], [Flame retardant UL94 test], [Adhesive strength], [Heat resistant holding power], [Volume specific resistance] were measured,
The evaluation results are shown in Tables 2 and 3.
【００２９】〔熱伝導性〕 剥離フィルムを剥がしたテープサンプルを厚みが約２
ｍｍになるよう積層し５０ｍｍ×１２０ｍｍの大きさに
切断し試験片とした。 室温で、迅速熱伝導率計ＱＴＭ５００（京都電子工業
社製）により、標準物質であるＰＥ発泡体、シリコン、
石英の熱伝導率を測定した。 各標準物質の上に試験片を接着し、同様に熱伝導率を
測定した。 の熱伝導率との熱伝導率の偏差をプロットし、内
挿法により熱伝導率を求めた。熱伝導率の算出にはＱＴ
Ｍ−Ｄ３（京都電子工業製）ソフトを用いた。[Thermal Conductivity] The tape sample from which the release film was peeled off had a thickness of about 2
mm and cut into a size of 50 mm × 120 mm to obtain a test piece. At room temperature, using a rapid thermal conductivity meter QTM500 (manufactured by Kyoto Electronics Manufacturing Co., Ltd.), PE foam, silicon,
The thermal conductivity of quartz was measured. A test piece was adhered on each standard material, and the thermal conductivity was measured similarly. Was plotted, and the thermal conductivity was determined by interpolation. QT for calculating thermal conductivity
MD-D3 (made by Kyoto Denshi Kogyo) software was used.
【００３０】〔難燃性ＵＬ９４試験〕ＵＬ規格（ＵＬ９
４「機器の部品用プラスチック材料の燃焼試験方法」）
に準じ、燃焼性試験を行い判断した。「ＶＴＭ−０」、
「ＶＴＭ−１」は以下の燃焼程度を示す基準である。[UL94 Flame Retardant Test] UL Standard (UL9
4 "Method of testing combustion of plastic materials for equipment parts")
A flammability test was performed in accordance with the above. "VTM-0",
"VTM-1" is a criterion indicating the following degree of combustion.
【００３１】フィルム状の試料を円筒型に保持し、１組
５枚の試料に対して各試料につき３秒間の接炎を２回行
い、その場合の燃焼時間の合計、燃焼距離、熱による貫
通の有無により下記の如く、クラス分類する。ＶＴＭ−
０はＶＴＭ−１よりも燃焼しにくい。A film-shaped sample is held in a cylindrical shape, and a set of five samples is subjected to flame contact twice for 3 seconds for each sample. In this case, the total burning time, burning distance, and heat penetration Is classified as follows depending on the presence or absence of VTM-
0 is less likely to burn than VTM-1.
【００３２】 燃焼クラス判定基準 ＶＴＭ−１ ＶＴＭ−０ 各試料の残炎燃焼時間−−−−−−−−−− ≦３０秒 ≦１０秒 ５枚の試料の燃焼時間合計−−−−−−−− ≦２５０秒 ≦５０秒 第２回接炎後の残炎時間＋無炎燃焼時間−− ≦６０秒 ≦３０秒 滴下物による綿への着火の有無−−−−−− なし なし クランプまでの残炎又は無炎燃焼の有無−− なし なしCombustion Class Judgment Standard VTM-1 VTM-0 Afterflame Burning Time of Each Sample ----- 30 seconds ≤ 10 seconds Total Burning Time of 5 Samples----------------------------------------- −− ≦ 250 seconds ≦ 50 seconds After-flame time after the second flame contact + flameless combustion time −− ≦ 60 seconds ≦ 30 seconds Presence or absence of ignition of cotton by dripping material −−−−−− None None Up to clamp Whether there is residual flame or flameless combustion --- None None
【００３３】〔接着力〕ポリエステルフィルム２５μｍ
で一方の粘着面をバッキングした２５ｍｍ×１００ｍｍ
のテープサンプルを、銅板に２ｋｇローラー１往復加圧
貼付し室温で１時間放置後、１８０°方向に剥離速度３
００ｍｍ／ｍｉｎで引き剥がし接着力を測定した。[Adhesion] Polyester film 25 μm
25mm x 100mm backing one adhesive side with
Tape sample was applied to a copper plate with a 2-kg roller and reciprocating pressure was applied and left at room temperature for 1 hour.
The peel strength was measured at 00 mm / min.
【００３４】〔定荷重剥離力〕ポリエステルフィルム２
５μｍで一方の粘着面をバッキングした１０ｍｍ×１５
０ｍｍのテープサンプルを、ステンレス板に接着面積が
１０ｍｍ×１００ｍｍになるように２ｋｇローラー８往
復加圧貼付する。４０℃で１時間放置後、室温下でサン
プルの一旦に２００ｇの荷重を吊し、１時間後の剥がれ
距離を測定した。[Constant load peeling force] Polyester film 2
10 mm x 15 with 5 µm backing one adhesive surface
A 2 kg roller 8 reciprocating pressure is applied to a 0 mm tape sample on a stainless steel plate so that the adhesive area becomes 10 mm × 100 mm. After leaving at 40 ° C. for 1 hour, a load of 200 g was temporarily suspended on the sample at room temperature, and the peeling distance after 1 hour was measured.
【００３５】〔耐熱保持力〕アルミ箔５０μｍで一方の
粘着面をバッキングしたテープサンプルを、ステンレス
板に貼付面積が２５ｍｍ×２５ｍｍになるよう２ｋｇロ
ーラー１往復加圧貼付し室温で３０分放置後、１２０℃
雰囲気下で１ｋｇの荷重を掛けテープサンプルが落下す
るまでの時間を測定した。２４時間以上落下しないテー
プサンプルに関しては「２４＜」と記載した。[Heat resistance] A tape sample having one adhesive surface backed with 50 μm aluminum foil was stuck on a stainless steel plate with a 2 kg roller in one reciprocating pressure so that the stuck area was 25 mm × 25 mm, and allowed to stand at room temperature for 30 minutes. 120 ° C
A load of 1 kg was applied under an atmosphere, and the time until the tape sample dropped was measured. "24 <" was described for a tape sample that did not drop for more than 24 hours.
【００３６】〔体積固有抵抗値〕タケダ理研製超絶縁／
微少電流計ＴＲ８６０１で測定した。測定温度は３０
℃、測定電圧は５００Ｖとした。[Volume resistivity] Takeda Riken super insulation /
It was measured with a microammeter TR8601. Measurement temperature is 30
C. and the measurement voltage was 500 V.
【００３７】[0037]
【表１】 [Table 1]
【００３８】表１に於ける、（メタ）アクリル酸エステ
ル共重合体Ａ，Ｂの配合量は１００部であり、水酸化ア
ルミは、昭和電工社製ハイジライトＨ３２、酸化アルミ
は、昭和電工社製アルミナＡＳ５０、窒化アルミは、東
洋アルミニウム社製ＵＭ、含窒素リン化合物は、チッソ
社製テラージュＣ６０を表す。更に、難燃助剤のアルコ
ールは脂肪族多価アルコールであり、広栄化学工業社製
のジペンタエリスリトール（ジペンタリット）、アルコ
ール誘導体は脂肪族多価アルコール誘導体であり、荒川
化学社製の重合ロジンペンタエリスリトールエステル
（Ｄ−１３５）である。架橋剤はエポキシ系架橋剤であ
る、綜研化学社製Ｅ−０５Ｘ（固形分０．５％）を使用
し、対感圧接着剤１００部当たりの添加量で示す。In Table 1, the amounts of the (meth) acrylate copolymers A and B were 100 parts, aluminum hydroxide was Hijilite H32 manufactured by Showa Denko KK, and aluminum oxide was Showa Denko KK Alumina AS50 and aluminum nitride represent UM manufactured by Toyo Aluminum Co., Ltd., and the nitrogen-containing phosphorus compound represents Terage C60 manufactured by Chisso Corporation. Further, the alcohol of the flame retardant aid is an aliphatic polyhydric alcohol, dipentaerythritol (dipentarit) manufactured by Koei Chemical Industry Co., Ltd., and the alcohol derivative is an aliphatic polyhydric alcohol derivative, and polymerized rosin pentamer manufactured by Arakawa Chemical Co., Ltd. Erythritol ester (D-135). As the crosslinking agent, E-05X (solid content: 0.5%) manufactured by Soken Chemical Co., Ltd., which is an epoxy-based crosslinking agent, is used, and the amount is shown per 100 parts of the pressure-sensitive adhesive.
【００３９】[0039]
【表２】 [Table 2]
【００４０】[0040]
【表３】 [Table 3]
【００４１】[0041]
【発明の効果】本発明の電気絶縁性の熱伝導難燃性感圧
接着剤及び感圧接着テープを使用することにより、ヒー
トシンク等と電子部品の接着作業性が向上でき、電子部
品が発生する熱をヒートシンク等の放熱装置に効率良く
伝えるため電子部品の誤作動を防止できる。また万一熱
が蓄積した場合も難燃性であるため火災等を防止でき
る。さらに発ガン性が疑われる三酸化アンチモン、ダイ
オキシン等を発生する可能性のあるハロゲン系、特にブ
ロモ系難燃剤を含有しないため、人体や環境への負荷を
低減できる。According to the present invention, the use of the electrically insulating heat conductive flame-retardant pressure-sensitive adhesive and the pressure-sensitive adhesive tape of the present invention can improve the workability of bonding an electronic component to a heat sink or the like, and the heat generated by the electronic component can be improved. Is efficiently transmitted to a heat radiating device such as a heat sink, thereby preventing malfunction of electronic components. Even if heat accumulates, it is flame-retardant and can prevent fire and the like. Furthermore, since it does not contain a halogen-based, particularly bromo-based flame retardant which may generate antimony trioxide, dioxin, etc. which are suspected of carcinogenicity, the burden on human bodies and the environment can be reduced.
───────────────────────────────────────────────────── フロントページの続き Ｆターム(参考） 4J004 AA10 AA17 AA18 AB01 CA06 CC02 DB02 EA05 FA05 4J040 BA202 DF041 DF051 HA136 HA206 HB11 HD28 JB09 KA36 KA42 LA08 NA15 NA16 NA19 PA23 ──────────────────────────────────────────────────続 き Continued on the front page F term (reference) 4J004 AA10 AA17 AA18 AB01 CA06 CC02 DB02 EA05 FA05 4J040 BA202 DF041 DF051 HA136 HA206 HB11 HD28 JB09 KA36 KA42 LA08 NA15 NA16 NA19 PA23
Claims (7)
モノマーからなる共重合体１００重量部と、熱伝導電気
絶縁性充填剤及び含窒素リン化合物の比率が８：２〜
３：７で総量が５０〜２００重量部を含有し、熱伝導率
が０．３Ｗ／ｍ・Ｋ以上であることを特徴とする電気絶
縁性の熱伝導難燃性感圧接着剤。Claims: 1. A 100 parts by weight copolymer of an alkyl (meth) acrylate-based monomer, a heat conductive and electrically insulating filler and a nitrogen-containing phosphorus compound in a ratio of 8: 2 to 2: 2.
3: An electrically insulating heat-conducting flame-retardant pressure-sensitive adhesive, characterized in that it has a total amount of 50 to 200 parts by weight and a heat conductivity of 0.3 W / m · K or more.
化物、金属窒化物、水和金属化合物からなる群から選ば
れる１種以上を含有する請求項１に記載の電気絶縁性の
熱伝導難燃性感圧接着剤。2. The electrically insulating heat conductive material according to claim 1, wherein the heat conductive and electrically insulating filler contains at least one selected from the group consisting of metal oxides, metal nitrides, and hydrated metal compounds. Flame retardant pressure sensitive adhesive.
あり、含窒素リン化合物がポリリン酸アンモニウムであ
る請求項２に記載の電気絶縁性の熱伝導難燃性感圧接着
剤。3. The pressure-sensitive adhesive according to claim 2, wherein the hydrated metal compound is aluminum hydroxide and the nitrogen-containing phosphorus compound is ammonium polyphosphate.
族多価アルコール及び／又は脂肪族多価アルコールの誘
導体を含有する請求項１〜３のいずれかに記載の電気絶
縁性の熱伝導難燃性感圧接着剤。4. The electrically insulating heat conductor according to claim 1, wherein the polyhydric alcohol further comprises an aliphatic polyhydric alcohol and / or a derivative of the aliphatic polyhydric alcohol as a flame retardant aid of the nitrogen-containing phosphorus compound. Flame retardant pressure sensitive adhesive.
系樹脂と脂肪族多価アルコールのエステル化物である請
求項１〜４いずれかに記載の電気絶縁性の熱伝導難燃性
感圧接着剤。5. The pressure-sensitive adhesive according to claim 1, wherein the aliphatic polyhydric alcohol derivative is an esterified product of a rosin resin and an aliphatic polyhydric alcohol.
モノマーを光重合して得られた共重合体である請求項１
〜５のいずれかに記載の電気絶縁性の熱伝導難燃性感圧
接着剤。6. A copolymer obtained by photopolymerizing an alkyl (meth) acrylate monomer.
6. An electrically insulating, heat-conducting, flame-retardant, pressure-sensitive adhesive according to any one of claims 1 to 5.
いずれかに記載の電気絶縁性の熱伝導難燃性感圧接着剤
を設け、熱伝導率が０．３Ｗ／ｍ・Ｋ以上であることを
特徴とする感圧接着テープ。7. An electrically insulating heat-conductive and flame-retardant pressure-sensitive adhesive according to claim 1 provided on at least one surface of a substrate, and having a heat conductivity of 0.3 W / m · K or more. A pressure-sensitive adhesive tape, characterized in that:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11088142A JP2000281997A (en) | 1999-03-30 | 1999-03-30 | Thermally conductive, flame-retardant pressure- sensitive adhesive and pressure-sensitive adhesive tape |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11088142A JP2000281997A (en) | 1999-03-30 | 1999-03-30 | Thermally conductive, flame-retardant pressure- sensitive adhesive and pressure-sensitive adhesive tape |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2000281997A true JP2000281997A (en) | 2000-10-10 |
Family
ID=13934697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11088142A Pending JP2000281997A (en) | 1999-03-30 | 1999-03-30 | Thermally conductive, flame-retardant pressure- sensitive adhesive and pressure-sensitive adhesive tape |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2000281997A (en) |
Cited By (21)
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|---|---|---|---|---|
| JP2002285121A (en) * | 2001-03-27 | 2002-10-03 | Nippon Zeon Co Ltd | Pressure-sensitive adhesive composition and sheet produced using the same |
| JP2002322447A (en) * | 2001-04-27 | 2002-11-08 | Nippon Zeon Co Ltd | Pressure sensitive adhesive composition and sheet using the same |
| JP2004027039A (en) * | 2002-06-26 | 2004-01-29 | Dainippon Ink & Chem Inc | Flame-retardant, thermoconductive, electric-insulating, self-adhesive product |
| JP2004277737A (en) * | 2003-03-18 | 2004-10-07 | Tesa Ag | Pressure-sensitive adhesive having flame retardance, method for producing the same and its use for pressure-sensitive adhesive tape |
| WO2004104129A1 (en) * | 2003-05-22 | 2004-12-02 | Zeon Corporation | Thermally conductive pressure-sensitive adhesive composition, thermally conductive sheet-like moldings, and process for the production of the moldings |
| JP2005105028A (en) * | 2003-09-29 | 2005-04-21 | Nippon Zeon Co Ltd | Heat conductive pressure-sensitive adhesive composition, heat conductive sheet-like molded product and method for producing the same |
| WO2005044875A1 (en) * | 2003-11-07 | 2005-05-19 | Soken Chemical & Engineering Co., Ltd. | Polymerizable composition and method for producing (meth)acrylic thermally conductive sheet |
| WO2005047412A3 (en) * | 2003-11-13 | 2005-07-07 | Lg Chemical Ltd | Adhesives having advanced flame-retardant property |
| WO2007149613A1 (en) * | 2006-06-23 | 2007-12-27 | Avery Dennison Corporation | Flame retardant pressure sensitive adhesive |
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1999
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