JP2011171523A - Curable electromagnetic shielding adhesive film and method for producing the same - Google Patents
Curable electromagnetic shielding adhesive film and method for producing the same Download PDFInfo
- Publication number
- JP2011171523A JP2011171523A JP2010034164A JP2010034164A JP2011171523A JP 2011171523 A JP2011171523 A JP 2011171523A JP 2010034164 A JP2010034164 A JP 2010034164A JP 2010034164 A JP2010034164 A JP 2010034164A JP 2011171523 A JP2011171523 A JP 2011171523A
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- Prior art keywords
- conductive
- acid
- electromagnetic wave
- wave shielding
- film
- 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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Images
Abstract
Description
本発明は,繰り返し屈曲を受けるフレキシブルプリント配線板などに貼着して、電気回路から発生する電磁ノイズを遮蔽する用途に好適に用いられる硬化性電磁波シールド性接着性フィルム及びその製造方法に関する。 The present invention relates to a curable electromagnetic shielding adhesive film and a method for producing the same, which are suitably used for an application of shielding electromagnetic noise generated from an electric circuit by being attached to a flexible printed wiring board or the like that is repeatedly bent.
フレキシブルプリント配線板は、屈曲性を有することから、近年のOA機器、通信機器、携帯電話などの更なる高性能化、小型化の要請に応えるべく、その狭く複雑な構造からなる筐体内部に電子回路を組み込むために多用されている。そうした電子回路のダウンサイズ化・高周波化に伴い、そこから発生する不要な電磁ノイズに対する対策がますます重要になってきている。そこで、フレキシブルプリント配線板に、電子回路から発生する電磁ノイズを遮蔽する電磁波シールド性接着フィルムを貼着することが従来よりおこなわれている。
この電磁波シールド性接着フィルム自体には、電磁波シールド性に加えて、貼り合わせたフレキシブルプリント配線板全体の耐屈曲性を損なわないよう、薄さと優れた耐屈曲性が要求される。そのため、電磁波シールド性接着フィルムとしては、厚さの薄い基材フィルム上に導電層を設けてなる基本的構造を有するものが広く知られている。
Since flexible printed wiring boards are flexible, they can be accommodated inside the casings of narrow and complex structures in order to meet the demands for higher performance and downsizing of recent office automation equipment, communication equipment, and mobile phones. Widely used to incorporate electronic circuits. With such downsizing and high frequency of electronic circuits, countermeasures against unnecessary electromagnetic noise generated therefrom are becoming more and more important. Therefore, an electromagnetic wave shielding adhesive film that shields electromagnetic noise generated from an electronic circuit has been conventionally attached to a flexible printed wiring board.
In addition to the electromagnetic wave shielding property, the electromagnetic wave shielding adhesive film itself is required to have thinness and excellent bending resistance so as not to impair the bending resistance of the bonded flexible printed wiring board as a whole. Therefore, an electromagnetic wave shielding adhesive film having a basic structure in which a conductive layer is provided on a thin base film is widely known.
従来の電磁波シールド性接着フィルムとしては、カバーフィルムの片面に、導電性接着剤層及び必要に応じて金属薄膜層からなるシールド層を有し、他方の面に接着剤層と離型性補強フィルムとが順次積層されてなる補強シールドフィルムが知られている(特許文献1参照)。
また、導電性接着剤層及び/または金属薄膜を有するシールド層と芳香族ポリアミド樹脂からなるベースフィルムを有するシールドフィルムが知られている(特許文献2参照)。
また、セパレートフィルムの片面に樹脂をコーティングしてカバーフィルムを形成し、前記カバーフィルムの表面に金属薄膜層と接着剤層とで構成されるシールド層を設けてなるシールド性接着フィルムが知られている(特許文献3)。
As a conventional electromagnetic wave shielding adhesive film, the cover film has a conductive adhesive layer on one side of the cover film and, if necessary, a shield layer made of a metal thin film layer, and the adhesive layer and the releasable reinforcing film on the other side. There is known a reinforcing shield film in which and are sequentially laminated (see Patent Document 1).
Further, a shield film having a base film made of a conductive adhesive layer and / or a shield layer having a metal thin film and an aromatic polyamide resin is known (see Patent Document 2).
Also known is a shielding adhesive film in which a cover film is formed by coating a resin on one side of a separate film, and a shield layer composed of a metal thin film layer and an adhesive layer is provided on the surface of the cover film. (Patent Document 3).
これら特許文献1〜3に開示される蒸着法やスパッタ法により得られる金属薄膜層を有するシールド性接着フィルムにおいては、金属薄膜層が脆い為耐屈曲性が不十分という問題点があった。
。
In the shielding adhesive film having a metal thin film layer obtained by the vapor deposition method or the sputtering method disclosed in these
.
さらに特許文献4に開示される電磁波シールドフィルムの導電性接着剤層中には、電磁波シールド性を向上させる為に導電性フィラーとして大量の銀粉を使用している為に、価格が高いというデメリットや、FPC回路と貼り合わせた場合、より大きな接着力を発現することが難しかった。さらに、導電性フィラーを大量に含むため、屈曲性に対するより高度な要求には応えられなかった。 Furthermore, in the conductive adhesive layer of the electromagnetic wave shielding film disclosed in Patent Document 4, since a large amount of silver powder is used as a conductive filler in order to improve the electromagnetic wave shielding properties, When it was bonded to an FPC circuit, it was difficult to express a larger adhesive force. Furthermore, since a large amount of conductive filler is contained, it has not been possible to meet higher requirements for flexibility.
一方、特許文献5には、保護物質で被覆された導電性物質に対し、イオン交換能を有する物質を作用させて、導電性被膜を製造する方法が記載されている。 On the other hand, Patent Document 5 describes a method for producing a conductive film by causing a substance having ion exchange ability to act on a conductive substance coated with a protective substance.
そこで、本発明は、フレキシブルプリント配線板などに貼付して電磁ノイズを遮蔽する用途に好適に用いられる電磁波シールド性接着フィルムであって、フレキシブルプリント配線板に貼着した後、十分な電磁波シールド性に加えて、鉛フリーハンダリフロー時の高温に耐え得る耐熱性を有し、従来よりも少ない導電性フィラー量で電磁波シールド性を発現し、従来よりも耐屈曲性に優れる電磁波シールド性接着フィルムを提供することを目的とする。
また、本発明は、このような優れた性能を有する電磁波シールド性接着フィルムを安価かつ安定的に製造する方法を提供することを目的とする。
Therefore, the present invention is an electromagnetic wave shielding adhesive film suitably used for the application of shielding electromagnetic noise by sticking to a flexible printed wiring board and the like, and after adhering to the flexible printed wiring board, sufficient electromagnetic wave shielding properties In addition, an electromagnetic wave shielding adhesive film that has heat resistance that can withstand high temperatures during lead-free solder reflow, expresses electromagnetic wave shielding properties with a smaller amount of conductive filler than before, and has better bending resistance than before. The purpose is to provide.
Moreover, an object of this invention is to provide the method of manufacturing the electromagnetic wave shielding adhesive film which has such outstanding performance cheaply and stably.
硬化性を有しない絶縁フィルム、導電性被膜、及び硬化性導電性接着剤層をこの順序で具備する、電磁波シールド性接着性フィルムであって、
前記導電性被膜が、導電性粒子が保護物質によって被覆されてなる平均粒子径が0.001〜0.5μmの被覆導電性粒子を含む分散体から形成された被膜であり、
前記硬化性導電性接着剤層が、硬化性絶縁性樹脂と、平均粒子径が1〜50μmの金属粉とを含有する、ことを特徴とする電磁波シールド性接着性フィルムに関する。
前記本発明の電磁波シールド性接着性フィルムにおいて、硬化性導電性接着剤層の単位体積当たりの金属粉の含有量は、0.2〜4.5(g/cm3)であることが好ましく、
導電性被膜の表面抵抗率は1×10−3〜5×10−1(Ω/□)、硬化性導電性接着剤層の表面抵抗率は1×10-2〜1×102(Ω/□)であり、導電性被膜の表面抵抗率が硬化性導電性接着剤層の表面抵抗率よりも相対的に小さいことが好ましい。
An electromagnetic wave shielding adhesive film comprising an insulating film having no curability, a conductive coating, and a curable conductive adhesive layer in this order,
The conductive film is a film formed from a dispersion containing coated conductive particles having an average particle diameter of 0.001 to 0.5 μm formed by covering conductive particles with a protective substance,
The curable conductive adhesive layer includes a curable insulating resin and a metal powder having an average particle diameter of 1 to 50 μm, and relates to an electromagnetic wave shielding adhesive film.
In the electromagnetic wave shielding adhesive film of the present invention, the content of the metal powder per unit volume of the curable conductive adhesive layer is preferably 0.2 to 4.5 (g / cm 3 ),
The surface resistivity of the conductive film is 1 × 10 -3 ~5 × 10 -1 (Ω / □), the surface resistivity of the cured conductive adhesive layer is 1 × 10 -2 ~1 × 10 2 (Ω / It is preferable that the surface resistivity of the conductive coating is relatively smaller than the surface resistivity of the curable conductive adhesive layer.
また、本発明は前記電磁波シールド性接着性フィルムの製造方法に関し、いずれも硬化性を有しない絶縁フィルム、導電性被膜、及び硬化性導電性接着剤層をこの順序で具備する、電磁波シールド性接着性フィルムの製造方法である。 The present invention also relates to a method for producing the electromagnetic wave shielding adhesive film, which comprises an insulating film having no curability, a conductive coating, and a curable conductive adhesive layer in this order. It is a manufacturing method of an adhesive film.
本発明により、従来よりも少ない導電性フィラー量で、フレキシブルプリント配線板に貼着した後、十分な電磁波シールド性を発現し、従来よりも耐屈曲性に優れる電磁波シールド性接着フィルムを提供することができる。 The present invention provides an electromagnetic wave shielding adhesive film that exhibits sufficient electromagnetic wave shielding properties after being attached to a flexible printed wiring board with a smaller amount of conductive filler than conventional ones, and is superior in bending resistance than conventional ones. Can do.
本発明の電磁波シールド性接着性フィルムは、前記したように、導電性被膜と硬化性導電性接着剤層という2つの導電層を具備するものである。本発明は、この2つの導電層を具備することによって、十分な電磁波シールド性を発現し、従来よりも耐屈曲性に優れる電磁波シールド性接着フィルムを提供することができるようになったものである。 As described above, the electromagnetic wave shielding adhesive film of the present invention comprises two conductive layers, ie, a conductive film and a curable conductive adhesive layer. By providing these two conductive layers, the present invention can provide an electromagnetic wave shielding adhesive film that expresses sufficient electromagnetic wave shielding properties and is superior in bending resistance than conventional ones. .
導電層のうちの1つ、硬化性導電性接着剤層について説明する。
硬化性導電性接着剤層は、本発明の電磁波シールド性接着性フィルムを被着体に貼着する機能と、後述する導電性被膜との導通を確保し、導電性被膜と一体となって電磁波シールド性を発現する機能を担う。被着体とは、電磁波シールド性接着性フィルムによって電磁波をシールドし、保護したい部材・物品である。
従って、硬化性導電性接着剤層は、接着性発現機能を担う硬化性絶縁性樹脂成分と、導電性発現機能を担う平均粒子径が1〜50μmの金属粉とを含有するものであり、単位体積当たりの金属粉の含有量は0.2〜4.5(g/cm3)である事が好ましい。
One of the conductive layers, the curable conductive adhesive layer, will be described.
The curable conductive adhesive layer secures continuity between the function of sticking the electromagnetic wave shielding adhesive film of the present invention to the adherend and the conductive film described later, and integrates the electromagnetic wave with the conductive film. It bears the function to express shielding properties. The adherend is a member / article to be protected by shielding electromagnetic waves with an electromagnetic wave shielding adhesive film.
Accordingly, the curable conductive adhesive layer contains a curable insulating resin component responsible for the adhesive expression function and metal powder having an average particle diameter of 1 to 50 μm responsible for the conductive expression function. The content of the metal powder per volume is preferably 0.2 to 4.5 (g / cm 3 ).
硬化性絶縁性樹脂としては、フェノール系、エポキシ系、ウレタン系、メラミン系、アルキッド系などの熱硬化性樹脂、α,β−不飽和二重結合を有する2官能以上のモノマーおよび/または単官能のモノマーの、ビニル型モノマー、アクリル型モノマー、アクリレート型もしくはメタクリレート型(以下、(メタ)アクリレート型という)モノマー等の電子線照射により硬化するモノマーを使用することができるが、その中でもカルボキシル基を有するポリウレタンポリウレア樹脂(A)とエポキシ樹脂(B)を含有する事が好ましい。 Examples of the curable insulating resin include phenolic, epoxy-based, urethane-based, melamine-based, alkyd-based thermosetting resins, bifunctional or higher monomers having an α, β-unsaturated double bond, and / or monofunctional. Among these monomers, monomers that cure by electron beam irradiation, such as vinyl monomers, acrylic monomers, acrylate monomers, or methacrylate monomers (hereinafter referred to as (meth) acrylate monomers), can be used. It is preferable to contain the polyurethane polyurea resin (A) and the epoxy resin (B).
ポリウレタンポリウレア樹脂(A)及びエポキシ樹脂(B)を含有する接着樹脂組成物は、金属粉を良く分散し、金属粉が含まれていても十分な接着力を発揮し、さらに、熱圧着時の接着剤層のしみ出しが少なく、鉛フリーハンダリフローに耐え得る、優れた耐熱性及び耐屈曲性を得ることができる。 The adhesive resin composition containing the polyurethane polyurea resin (A) and the epoxy resin (B) disperses the metal powder well, exhibits a sufficient adhesive force even when the metal powder is contained, and further, at the time of thermocompression bonding The exudation of the adhesive layer is small, and excellent heat resistance and bending resistance that can withstand lead-free solder reflow can be obtained.
硬化性導電性接着剤層に含有される、硬化性絶縁性樹脂として使用されるポリウレタンポリウレア樹脂(A)は、カルボキシル基を有するジオール化合物(a1)と、数平均分子量500〜8000である、(a1)以外のポリオール(a2)及び有機ジイソシアネート(a3)とを反応させて得られる、末端にイソシアネート基を有するウレタンプレポリマー(a4)と、ポリアミノ化合物(a5)とを反応させて得られるものである。
カルボキシル基を有するジオール化合物(a1)としては、ジメチロール酢酸、ジメチロールプロピオン酸、ジメチロールブタン酸、ジメチロールペンタン酸等のジメチロールアルカン酸や、ジヒドロキシコハク酸、ジヒドロキシ安息香酸等が挙げられる。特に反応性、溶解性点から、ジメチロールプロピオン酸、ジメチロールブタン酸が好ましい。
The polyurethane polyurea resin (A) used as the curable insulating resin contained in the curable conductive adhesive layer has a diol compound (a1) having a carboxyl group and a number average molecular weight of 500 to 8000. A product obtained by reacting a urethane prepolymer (a4) having an isocyanate group at a terminal obtained by reacting a polyol (a2) other than a1) and an organic diisocyanate (a3) with a polyamino compound (a5). is there.
Examples of the diol compound (a1) having a carboxyl group include dimethylol alkanoic acids such as dimethylolacetic acid, dimethylolpropionic acid, dimethylolbutanoic acid and dimethylolpentanoic acid, dihydroxysuccinic acid, and dihydroxybenzoic acid. In particular, dimethylolpropionic acid and dimethylolbutanoic acid are preferable from the viewpoint of reactivity and solubility.
数平均分子量500〜8000である、(a1)以外のポリオール(a2)は、一般にポリウレタン樹脂を構成するポリオール成分として知られている、カルボキシル基を有するジオール化合物(a1)以外のポリオールである。前記ポリオール(a2)の数平均分子量(Mn)は、得られるポリウレタンポリウレア樹脂(A)の耐熱性、接着強度、溶解性等を考慮して適宜決定されるが、好ましくは1000〜5000である。Mnが500未満であると、得られるポリウレタンポリウレア樹脂(A)中のウレタン結合が多くなり過ぎ、ポリマー骨格の柔軟性が低下してフレキシブルプリント配線板への接着性が低下する傾向があり、また、Mnが8000を越えると、ジオール化合物(a1)由来のカルボキシル基の、ポリウレタンポリウレア樹脂(A)中における数が減少する。その結果、エポキシ樹脂との反応点が減少するため、得られる導電性硬化接着剤層の耐ハンダリフロー性が低下する傾向にある。 The polyol (a2) other than (a1) having a number average molecular weight of 500 to 8000 is a polyol other than the diol compound (a1) having a carboxyl group, which is generally known as a polyol component constituting the polyurethane resin. The number average molecular weight (Mn) of the polyol (a2) is appropriately determined in consideration of the heat resistance, adhesive strength, solubility and the like of the resulting polyurethane polyurea resin (A), and is preferably 1000 to 5000. When Mn is less than 500, the number of urethane bonds in the resulting polyurethane polyurea resin (A) increases too much, and the flexibility of the polymer skeleton tends to decrease and the adhesion to the flexible printed wiring board tends to decrease. When Mn exceeds 8000, the number of carboxyl groups derived from the diol compound (a1) in the polyurethane polyurea resin (A) decreases. As a result, since the reaction point with the epoxy resin is reduced, the solder reflow resistance of the obtained conductive cured adhesive layer tends to be lowered.
数平均分子量500〜8000である、(a1)以外のポリオール(a2)としては、各種のポリエーテルポリオール類、ポリエステルポリオール類、ポリカーボネートポリオール類、ポリブタジエングリコール類等が使用できる。
ポリエーテルポリオール類としては、酸化エチレン、酸化プロピレン、テトラヒドロフランなどの重合体または共重合体等が挙げられる。
As the polyol (a2) other than (a1) having a number average molecular weight of 500 to 8000, various polyether polyols, polyester polyols, polycarbonate polyols, polybutadiene glycols and the like can be used.
Examples of polyether polyols include polymers or copolymers such as ethylene oxide, propylene oxide, and tetrahydrofuran.
ポリエステルポリオール類としては、エチレングリコール、1,2−プロパンジオール、1,3−プロパンジオール、1,3−ブタンジオール、1,4−ブタンジオール、ネオペンチルグリコール、ペンタンジオール、3−メチル−1,5−ペンタンジオール、ヘキサンジオール、オクタンジオール、1,4−ブチレンジオール、ジエチレングリコール、トリエチレングリコール、ジプロピレングリコール、もしくはダイマージオール等の飽和または不飽和の低分子ジオール類とアジピン酸、フタル酸、イソフタル酸、テレフタル酸、マレイン酸、フマル酸、コハク酸、シュウ酸、マロン酸、グルタル酸、ピメリン酸、スベリン酸、アゼライン酸、もしくはセバシン酸等のジカルボン酸類、またはこれらの無水物類を反応させて得られるポリエステルポリオール類や、n−ブチルグリシジルエーテル、又は2−エチルヘキシルグリシジルエーテル等のアルキルグリシジルエーテル類、バーサティック酸グリシジルエステル等のモノカルボン酸グリシジルエステル類と上記のジカルボン酸類の無水物類とをアルコール類などの水酸基含有化合物の存在下で反応させて得られるポリエステルポリオール類、または環状エステル化合物を開環重合して得られるポリエステルポリオール類が挙げられる。 Polyester polyols include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, neopentyl glycol, pentanediol, 3-methyl-1, Saturated or unsaturated low molecular weight diols such as 5-pentanediol, hexanediol, octanediol, 1,4-butylenediol, diethylene glycol, triethylene glycol, dipropylene glycol, or dimer diol, and adipic acid, phthalic acid, isophthalic acid By reacting dicarboxylic acids such as acid, terephthalic acid, maleic acid, fumaric acid, succinic acid, oxalic acid, malonic acid, glutaric acid, pimelic acid, suberic acid, azelaic acid or sebacic acid, or their anhydrides. Poly obtained Steal polyols, alkyl glycidyl ethers such as n-butyl glycidyl ether or 2-ethylhexyl glycidyl ether, monocarboxylic glycidyl esters such as versatic acid glycidyl ester and anhydrides of the above dicarboxylic acids and alcohols And polyester polyols obtained by reacting in the presence of a hydroxyl group-containing compound such as, or polyester polyols obtained by ring-opening polymerization of a cyclic ester compound.
ポリカーボネートポリオール類としては、例えば、
1)グリコールまたはビスフェノールと炭酸エステルとの反応生成物、あるいは
2)グリコールまたはビスフェノールにアルカリの存在下でホスゲンを反応させて得られる反応生成物等が使用できる。
上記1)または2)の場合に用いられるグリコールとしては、エチレングリコール、プロピレングリコール、ジプロピレングリコール、ジエチレングリコール、トリエチレングリコール、ブチレングリコール、3−メチル−1,5−ペンタンジオール、2−メチル−1,8−オクタンジオール、3,3’−ジメチロールヘプタン、ポリオキシエチレングリコール、ポリオキシプロピレングリコール、プロパンジオール、1,3−ブタンジオール、1,4−ブタンジオール、1,5−ペンタンジオール、1,6−ヘキサンジオール、1,9−ノナンジオール、ネオペンチルグリコール、オクタンジオール、ブチルエチルペンタンジオール、2−エチル−1,3−ヘキサンジオール、シクロヘキサンジオール、3,9−ビス(1,1−ジメチル−2−ヒドロキシエチル、2,2,8,10−テトラオキソスピロ〔5.5〕ウンデカンが挙げられる。
Examples of polycarbonate polyols include:
1) A reaction product of glycol or bisphenol and a carbonate ester, or 2) a reaction product obtained by reacting glycol or bisphenol with phosgene in the presence of alkali can be used.
Examples of the glycol used in the case of 1) or 2) include ethylene glycol, propylene glycol, dipropylene glycol, diethylene glycol, triethylene glycol, butylene glycol, 3-methyl-1,5-pentanediol, and 2-methyl-1. , 8-octanediol, 3,3′-dimethylolheptane, polyoxyethylene glycol, polyoxypropylene glycol, propanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1 , 6-hexanediol, 1,9-nonanediol, neopentyl glycol, octanediol, butylethylpentanediol, 2-ethyl-1,3-hexanediol, cyclohexanediol, 3,9-bis (1,1-dimethyl) -2 -Hydroxyethyl, 2,2,8,10-tetraoxospiro [5.5] undecane.
また、上記1)または2)の場合に用いられるビスフェノールとしては、例えば、ビスフェノールAやビスフェノールF等のビスフェノール類や、これらのビスフェノール類にエチレンオキサイドまたはプロピレンオキサイド等のアルキレンオキサイドを付加させた化合物等が挙げられる。
また、上記1)の場合に用いられる炭酸エステルとしては、例えば、ジメチルカーボネート、ジエチルカーボネート、ジフェニルカーボネート、エチレンカーボネート、プロピレンカーボネート等が挙げられる。
Examples of the bisphenol used in the case 1) or 2) include, for example, bisphenols such as bisphenol A and bisphenol F, and compounds obtained by adding alkylene oxides such as ethylene oxide or propylene oxide to these bisphenols. Is mentioned.
Examples of the carbonic acid ester used in the case of 1) include dimethyl carbonate, diethyl carbonate, diphenyl carbonate, ethylene carbonate, propylene carbonate, and the like.
数平均分子量500〜8000である、(a1)以外のポリオール(a2)として例示した各種ポリオールは、単独で用いても、2種類以上併用してもよい。
更に、得られるポリウレタンポリウレア樹脂(A)の性能が失われない範囲内で、カルボキシル基を有するジオール化合物(a1)と、数平均分子量500〜8000である、(a1)以外のポリオール(a2)及び有機ジイソシアネート(a3)とを反応させる際に、カルボキシル基を有するジオール化合物(a1)以外の低分子ジオール類を併用しても良い。併用可能な低分子ジオール類としては、たとえば、数平均分子量500〜8000である、(a1)以外のポリオール(a2)の製造に用いられる各種低分子ジオール等が挙げられる。
Various polyols exemplified as the polyol (a2) other than (a1) having a number average molecular weight of 500 to 8000 may be used alone or in combination of two or more.
Furthermore, within the range in which the performance of the resulting polyurethane polyurea resin (A) is not lost, a diol compound (a1) having a carboxyl group, a polyol (a2) other than (a1) having a number average molecular weight of 500 to 8000, and When reacting with the organic diisocyanate (a3), low molecular diols other than the diol compound (a1) having a carboxyl group may be used in combination. Examples of the low molecular diols that can be used in combination include various low molecular diols having a number average molecular weight of 500 to 8000, which are used in the production of a polyol (a2) other than (a1).
ウレタンプレポリマー(a4)を合成する際に、カルボキシル基を有するジオール化合物(a1)と、数平均分子量500〜8000である、(a1)以外のポリオール(a2)とは、数平均分子量500〜8000の他のポリオール(a2)1モルに対して、カルボキシル基を有するジオール化合物(a1)0.1モル〜4.0モルとなる比率で用いることが好ましく、0.2モル〜3.0モルとなる比率で用いることがより好ましい。(a2)1モルに対する(a1)の使用量が0.1モルより少ないと、エポキシ樹脂(B)と架橋可能なカルボキシル基が少なくなり、耐ハンダリフロー性が低下する傾向にある。また、4.0モルより多いと、接着性が低下する傾向にある。 In synthesizing the urethane prepolymer (a4), the diol compound (a1) having a carboxyl group and the polyol (a2) other than (a1) having a number average molecular weight of 500 to 8000 are the number average molecular weight of 500 to 8000. It is preferably used in a ratio of 0.1 mol to 4.0 mol of the diol compound (a1) having a carboxyl group with respect to 1 mol of the other polyol (a2), It is more preferable to use at the ratio. (A2) When the amount of (a1) used relative to 1 mol is less than 0.1 mol, the epoxy resin (B) and the crosslinkable carboxyl group tend to decrease, and the solder reflow resistance tends to be lowered. On the other hand, when the amount is more than 4.0 mol, the adhesiveness tends to decrease.
有機ジイソシアネート(a3)としては、芳香族ジイソシアネート、脂肪族ジイソシアネート、脂環族イソシアネート、またはこれらの混合物を使用できるが、特にイソホロンジイソシアネートが好ましい。 As the organic diisocyanate (a3), aromatic diisocyanate, aliphatic diisocyanate, alicyclic isocyanate, or a mixture thereof can be used, and isophorone diisocyanate is particularly preferable.
芳香族ジイソシアネートとしては、例えば、1,5−ナフチレンジイソシアネート、4,4′−ジフェニルメタンジイソシアネート、4,4′−ジフェニルジメチルメタンジイソシアネート、4,4′−ベンジルイソシアネート、ジアルキルジフェニルメタンジイソシアネート、テトラアルキルジフェニルメタンジイソシアネート、1,3−フェニレンジイソシアネート、1,4−フェニレンジイソシアネート、トリレンジイソシアネート、またはキシリレンジイソシアネート等が挙げられる。 Examples of aromatic diisocyanates include 1,5-naphthylene diisocyanate, 4,4'-diphenylmethane diisocyanate, 4,4'-diphenyldimethylmethane diisocyanate, 4,4'-benzyl isocyanate, dialkyldiphenylmethane diisocyanate, tetraalkyldiphenylmethane diisocyanate. 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, tolylene diisocyanate, xylylene diisocyanate, and the like.
脂肪族ジイシシアネートとしては、例えば、ブタン−1,4−ジイソシアネート、ヘキサメチレンジイソシアネート、2,2,4−トリメチルヘキサメチレンジイソシアネート、またはリジンジイソシアネート等が挙げられる。 Examples of the aliphatic diisocyanate include butane-1,4-diisocyanate, hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, or lysine diisocyanate.
脂環族ジイソシアネートとしては、例えば、シクロヘキサン−1,4−ジイソシアネート、イソホロンジイソシアネート、ジシクロヘキシルメタン−4,4′−ジイソシアネート、1,3−ビス(イソシアネートメチル)シクロヘキサン、またはメチルシクロヘキサンジイソシアネート等が挙げられる。 Examples of the alicyclic diisocyanate include cyclohexane-1,4-diisocyanate, isophorone diisocyanate, dicyclohexylmethane-4,4′-diisocyanate, 1,3-bis (isocyanatomethyl) cyclohexane, methylcyclohexane diisocyanate, and the like.
末端にイソシアネート基を有するウレタンプレポリマー(a4)は、カルボキシル基を有するジオール化合物(a1)と、数平均分子量500〜8000である、(a1)以外のポリオール(a2)及び有機ジイソシアネート(a3)とを反応させることにより得られる。末端にイソシアネート基を有するウレタンプレポリマー(a4)を合成する際の条件は、イソシアネート基が過剰になるようにする他にとくに限定はないが、イソシアネート基/水酸基の当量比が1.2/1〜3/1の範囲内になるような割合で、カルボキシル基を有するジオール化合物(a1)と、数平均分子量500〜8000である、(a1)以外のポリオール(a2)及び有機ジイソシアネート(a3)とを反応させることが好ましい。また、反応温度は通常常温〜120℃であるが、更に製造時間、副反応の制御の面から好ましくは60〜100℃である。 The urethane prepolymer (a4) having an isocyanate group at the end includes a diol compound (a1) having a carboxyl group, a polyol (a2) other than (a1) and an organic diisocyanate (a3) having a number average molecular weight of 500 to 8000. It is obtained by reacting. The conditions for synthesizing the urethane prepolymer (a4) having an isocyanate group at the terminal are not particularly limited except that the isocyanate group becomes excessive, but the equivalent ratio of isocyanate group / hydroxyl group is 1.2 / 1. A diol compound (a1) having a carboxyl group, a polyol (a2) other than (a1), and an organic diisocyanate (a3) having a number average molecular weight of 500 to 8000 in a ratio so as to fall within a range of ˜3 / 1. Is preferably reacted. The reaction temperature is usually from room temperature to 120 ° C., but preferably from 60 to 100 ° C. from the viewpoint of production time and side reaction control.
ポリウレタンポリウレア樹脂(A)は、末端にイソシアネート基を有するウレタンプレポリマー(a4)と、ポリアミノ化合物(a5)とを反応させて得られる。
ポリアミノ化合物(a5)としては、エチレンジアミン、プロピレンジアミン、ヘキサメチレンジアミン、ジエチレントリアミン、トリエチレンテトラミン、イソホロンジアミン、ジシクロヘキシルメタン−4,4′−ジアミンの他、2−(2−アミノエチルアミノ)エタノール、2−ヒドロキシエチルエチレンジアミン、2−ヒドロキシエチルプロピレンジアミン、ジ−2−ヒドロキシエチルエチレンジアミン、ジ−2−ヒドロキシプロピルエチレンジアミン等の水酸基を有するアミン類も使用することができる。なかでも、イソホロンジアミンが好適に使用される。
The polyurethane polyurea resin (A) is obtained by reacting the urethane prepolymer (a4) having an isocyanate group at the terminal with the polyamino compound (a5).
Examples of the polyamino compound (a5) include ethylenediamine, propylenediamine, hexamethylenediamine, diethylenetriamine, triethylenetetramine, isophoronediamine, dicyclohexylmethane-4,4′-diamine, 2- (2-aminoethylamino) ethanol, 2 Amines having a hydroxyl group such as -hydroxyethylethylenediamine, 2-hydroxyethylpropylenediamine, di-2-hydroxyethylethylenediamine, and di-2-hydroxypropylethylenediamine can also be used. Of these, isophoronediamine is preferably used.
末端にイソシアネート基を有するウレタンプレポリマー(a4)とポリアミノ化合物(a5)とを反応させてポリウレタンポリウレア樹脂(A)を合成するときには、分子量を調整する為に反応停止剤を併用することができる。反応停止剤としては、ジ−n−ブチルアミン等のジアルキルアミン類、ジエタノールアミン等のジアルカノールアミン類や、エタノール、イソプロピルアルコール等のアルコール類が使用できる。 When synthesizing the polyurethane polyurea resin (A) by reacting the urethane prepolymer (a4) having an isocyanate group at the terminal with the polyamino compound (a5), a reaction terminator can be used in combination to adjust the molecular weight. As the reaction terminator, dialkylamines such as di-n-butylamine, dialkanolamines such as diethanolamine, and alcohols such as ethanol and isopropyl alcohol can be used.
末端にイソシアネート基を有するウレタンプレポリマー(a4)、ポリアミノ化合物(a5)及び必要に応じて反応停止剤を反応させる際の条件は、とくに限定はないが、ウレタンプレポリマー(a4)が有するイソシアネート基に対する、ポリアミノ化合物(a5)及び反応停止剤中のアミノ基の合計の当量比が0.5〜1.3の範囲内であることが好ましい。当量比が0.5未満の場合には、耐ハンダリフロー性が不十分になりやすく、1.3より多い場合には、ポリアミノ化合物(a5)及び/または反応停止剤が未反応のまま残存し、臭気が残りやすくなる。 The conditions for reacting the urethane prepolymer (a4) having an isocyanate group at the terminal, the polyamino compound (a5) and, if necessary, the reaction terminator are not particularly limited, but the isocyanate group possessed by the urethane prepolymer (a4) The total equivalent ratio of the amino group in the polyamino compound (a5) and the reaction terminator is preferably in the range of 0.5 to 1.3. When the equivalent ratio is less than 0.5, the solder reflow resistance tends to be insufficient, and when it exceeds 1.3, the polyamino compound (a5) and / or the reaction terminator remain unreacted. , The odor tends to remain.
ポリウレタンポリウレア樹脂(A)を合成する際に用いられる溶剤としては、ベンゼン、トルエン、キシレン等の芳香族系溶剤、メタノール、エタノール、イソプロパノール、n−ブタノール等のアルコール系溶剤、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン系溶剤、酢酸エチル、酢酸ブチル等のエステル系溶剤が挙げられる。
これらの溶剤は、1種を単独で、または2種以上を混合して用いることができる。
得られるポリウレタンポリウレア樹脂(A)の重量平均分子量は、5000〜100000の範囲にあることが好ましい。重量平均分子量が5000に満たない場合には、耐ハンダリフロー性が劣る傾向にあり、100000を越える場合には、接着性が低下する傾向にある。
Solvents used for synthesizing the polyurethane polyurea resin (A) include aromatic solvents such as benzene, toluene and xylene, alcohol solvents such as methanol, ethanol, isopropanol and n-butanol, acetone, methyl ethyl ketone and methyl isobutyl. Examples include ketone solvents such as ketones and ester solvents such as ethyl acetate and butyl acetate.
These solvent can be used individually by 1 type or in mixture of 2 or more types.
It is preferable that the weight average molecular weight of the obtained polyurethane polyurea resin (A) exists in the range of 5000-100000. When the weight average molecular weight is less than 5000, the solder reflow resistance tends to be inferior, and when it exceeds 100,000, the adhesion tends to be lowered.
また、硬化性導電性接着剤層に含有されるエポキシ樹脂(B)は、2個以上のエポキシ基を有する樹脂であり、液状であっても固形状であってもよい。
エポキシ樹脂(B)としては、ビスフェノールA型エポキシ樹脂、ビスフェノールF型エポキシ樹脂、ビスフェノールS型エポキシ樹脂、スピロ環型エポキシ樹脂、ナフタレン型エポキシ樹脂、ビフェニル型エポキシ樹脂、テルペン型エポキシ樹脂、トリス(グリシジルオキシフェニル)メタン、テトラキス(グリシジルオキシフェニル)エタンなどのグリシジルエーテル型エポキシ樹脂、テトラグリシジルジアミノジフェニルメタンなどのグリシジルアミン型エポキシ樹脂、テトラブロムビスフェノールA型エポキシ樹脂、クレゾールノボラック型エポキシ樹脂、フェノールノボラック型エポキシ樹脂、α−ナフトールノボラック型エポキシ樹脂、臭素化フェノールノボラック型エポキシ樹脂等が挙げられる。これらのエポキシ樹脂は、1種を単独で、または2種以上を組み合わせて用いることができる。これらのうち高接着性、耐熱性の点から、ビスフェノールA型エポキシ樹脂やクレゾールノボラック型エポキシ樹脂、またはテトラキス(グリシジルオキシフェニル)エタン型エポキシ樹脂を用いることが好ましい。
The epoxy resin (B) contained in the curable conductive adhesive layer is a resin having two or more epoxy groups and may be liquid or solid.
As the epoxy resin (B), bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, spiro ring type epoxy resin, naphthalene type epoxy resin, biphenyl type epoxy resin, terpene type epoxy resin, tris (glycidyl) Glycidyl ether type epoxy resins such as oxyphenyl) methane and tetrakis (glycidyloxyphenyl) ethane, Glycidylamine type epoxy resins such as tetraglycidyldiaminodiphenylmethane, Tetrabromobisphenol A type epoxy resin, Cresol novolac type epoxy resin, Phenol novolak type epoxy resin Examples thereof include resins, α-naphthol novolac type epoxy resins, brominated phenol novolac type epoxy resins and the like. These epoxy resins can be used individually by 1 type or in combination of 2 or more types. Among these, it is preferable to use a bisphenol A type epoxy resin, a cresol novolac type epoxy resin, or a tetrakis (glycidyloxyphenyl) ethane type epoxy resin from the viewpoint of high adhesion and heat resistance.
本発明で用いられる硬化性導電性接着剤層において、エポキシ樹脂(B)とポリウレタンポリウレア樹脂(A)との配合比率は、ポリウレタンポリウレア樹脂(A)100重量部に対して、エポキシ樹脂(B)3〜200重量部であることが好ましく、5〜100重量部であることがより好ましい。(A)100重量部に対して(B)が3重量部より少ないと、耐ハンダリフロー性が低くなる傾向がある。一方、(B)が200重量部より多いと、接着性が低下する傾向がある
硬化性導電性接着剤層には、耐熱性や耐屈曲性等の性能を損なわない範囲で、フェノール系樹脂、シリコーン系樹脂、ユリア系樹脂、アクリル系樹脂、ポリエステル系樹脂、ポリアミド系樹脂、ポリイミド系樹脂などを含有させることができる。
In the curable conductive adhesive layer used in the present invention, the blending ratio of the epoxy resin (B) and the polyurethane polyurea resin (A) is 100 parts by weight of the polyurethane polyurea resin (A), and the epoxy resin (B). The amount is preferably 3 to 200 parts by weight, and more preferably 5 to 100 parts by weight. (A) When (B) is less than 3 parts by weight with respect to 100 parts by weight, the solder reflow resistance tends to be low. On the other hand, if the amount of (B) is more than 200 parts by weight, the adhesiveness tends to decrease. The curable conductive adhesive layer has a phenolic resin, as long as the performance such as heat resistance and flex resistance is not impaired. Silicone resin, urea resin, acrylic resin, polyester resin, polyamide resin, polyimide resin and the like can be contained.
また、硬化性導電性接着剤層に含有される金属粉は、接着剤層に導電性を付与するものであり、金属粉の種類としては、例えば、金、銀、銅、白金、パラジウム、タングステン、チタン、インジウム、イリジウム、ロジウム、コバルト、鉄、ニッケル等が挙げられる。中でも導電性、コストの面から銀が好ましい。
また、金属粉の形状としては、球状、フレーク状、樹枝状、繊維状などが挙げられる。その中でも少量で導電性が発現することができるフレーク状の金属粉が好ましい。
Moreover, the metal powder contained in the curable conductive adhesive layer imparts conductivity to the adhesive layer. Examples of the metal powder include gold, silver, copper, platinum, palladium, and tungsten. , Titanium, indium, iridium, rhodium, cobalt, iron, nickel and the like. Among these, silver is preferable from the viewpoint of conductivity and cost.
In addition, examples of the shape of the metal powder include a spherical shape, a flake shape, a dendritic shape, and a fibrous shape. Among them, flaky metal powder that can exhibit conductivity in a small amount is preferable.
硬化性導電性接着剤層における金属粉の含有量は、必要とする電磁波シールド効果の度合いによって異なるが、硬化性導電性接着剤層の単位体積当たりの金属粉の含有量が0.2〜4.5(g/cm3)である事が好ましい。金属粉の含有量が0.2(g/cm3)より少ないと、十分なシールド性を得る事ができず、4.5(g/cm3)より多いと、接着性及び屈曲性が低下する。
硬化性導電性接着剤層の単位体積当たりの金属粉の含有量は、用いた金属粉の比重と配合量、接着剤層の厚みから理論的に求めることができる。
The content of the metal powder in the curable conductive adhesive layer varies depending on the required degree of electromagnetic shielding effect, but the content of the metal powder per unit volume of the curable conductive adhesive layer is 0.2-4. 0.5 (g / cm 3 ) is preferable. If the content of the metal powder is less than 0.2 (g / cm 3 ), sufficient shielding properties cannot be obtained, and if it is more than 4.5 (g / cm 3 ), the adhesiveness and flexibility are deteriorated. To do.
The content of the metal powder per unit volume of the curable conductive adhesive layer can be theoretically determined from the specific gravity and blending amount of the used metal powder and the thickness of the adhesive layer.
また、硬化性導電性接着剤層の表面抵抗率は、1×10-2〜1×102(Ω/□)である事が好ましく、より好ましくは1×10−1〜1×101(Ω/□)である。硬化性導電性接着剤層の表面抵抗率が1×10−2よりも小さい場合、使用する金属粉の種類によっては金属粉自体の抵抗率よりも小さくなるため実用的ではない。また、1×102よりも大きい場合、導電性粒子層と導通がとりにくくなり、その結果として電磁波シールド性が悪くなる
なお、硬化性導電性接着剤層の表面抵抗率は、本発明の電磁波シールド性接着性フィルム中の硬化性導電性接着剤層を形成する際と同条件にて、絶縁性シート状に形成した硬化性導電性接着剤層について求めたものである。
The surface resistivity of the curable conductive adhesive layer is preferably 1 × 10 −2 to 1 × 10 2 (Ω / □), more preferably 1 × 10 −1 to 1 × 10 1 ( Ω / □). When the surface resistivity of the curable conductive adhesive layer is smaller than 1 × 10 −2 , depending on the type of the metal powder used, the resistivity is lower than the resistivity of the metal powder itself, which is not practical. Moreover, when larger than 1 * 10 < 2 >, it becomes difficult to take electrical continuity with an electroconductive particle layer, and as a result, electromagnetic wave shielding property worsens.
The surface resistivity of the curable conductive adhesive layer was formed into an insulating sheet under the same conditions as those for forming the curable conductive adhesive layer in the electromagnetic wave shielding adhesive film of the present invention. This is obtained for the curable conductive adhesive layer.
さらに本発明で用いられる硬化性導電性接着剤層の厚みは、1〜20μmであることが好ましく、2〜10μmであることがより好ましい。硬化性導電性接着剤層の厚みが1μmよりも薄いと、接着力が発現しにくく被着体から剥がれやすい。一方、硬化性導電性接着剤層の厚みが20μmよりも厚いと屈曲性が低下する。 Furthermore, the thickness of the curable conductive adhesive layer used in the present invention is preferably 1 to 20 μm, and more preferably 2 to 10 μm. When the thickness of the curable conductive adhesive layer is thinner than 1 μm, the adhesive force is hardly expressed and is easily peeled off from the adherend. On the other hand, if the thickness of the curable conductive adhesive layer is thicker than 20 μm, the flexibility is lowered.
ポリウレタンポリウレア樹脂(A)とエポキシ樹脂(B)との合計100重量部に対して、金属粉は10〜400重量部であることが好ましく、50〜300重量部であることがより好ましく、70〜120重量部であることがさらに好ましい。金属粉の含有量が10重量部を下回ると、金属粉同士が十分に接触せず、高い導電性が得られず、電磁波シールド効果が不十分となりやすい。また、金属粉の含有量が400重量部を超えると、硬化性導電性接着剤層中の金属粉の量が過多となり、硬化性導電性接着剤層の後述する剥離性フィルム1への密着性や被着体への接着力が低下する。
The metal powder is preferably 10 to 400 parts by weight, more preferably 50 to 300 parts by weight, with respect to 100 parts by weight of the total of the polyurethane polyurea resin (A) and the epoxy resin (B). More preferably, it is 120 parts by weight. When the content of the metal powder is less than 10 parts by weight, the metal powders are not sufficiently in contact with each other, high conductivity is not obtained, and the electromagnetic wave shielding effect tends to be insufficient. Moreover, when content of a metal powder exceeds 400 weight part, the quantity of the metal powder in a curable conductive adhesive layer will become excess, and the adhesiveness to the
金属粉の粒子径は、1μm〜50μmの範囲内であり、好ましくは3μm〜25μmである。金属粉の粒子径が1μmよりも小さいと、導電性を発現させるために導電性接着剤中に大量の金属粉を添加する必要があり、大量に金属粉を加えると接着力の低下に繋がる。また、粒子径が50μmよりも大きいと、薄膜の導電性接着剤層を設ける際に、表面に凹凸が生じ、均一で平滑な導電性接着剤層が得られなくなり、接着力の低下及び屈曲性低下の原因となる。 The particle diameter of the metal powder is in the range of 1 μm to 50 μm, preferably 3 μm to 25 μm. If the particle diameter of the metal powder is smaller than 1 μm, it is necessary to add a large amount of metal powder to the conductive adhesive in order to develop conductivity, and adding a large amount of metal powder leads to a decrease in adhesive strength. On the other hand, if the particle diameter is larger than 50 μm, when a thin conductive adhesive layer is provided, the surface becomes uneven, and a uniform and smooth conductive adhesive layer cannot be obtained, resulting in a decrease in adhesive strength and flexibility. Causes a drop.
なお、上記平均粒子径とは、動的光散乱法を利用した粒子径分布測定装置(例えば、日機装株式会社製、マイクロトラックまたはナノトラック等)により測定された値であり、D50を示す。 In addition, the said average particle diameter is a value measured with the particle diameter distribution measuring apparatus (For example, Nikkiso Co., Ltd. make, a micro track or a nano track etc.) using a dynamic light scattering method, and shows D50.
硬化性導電性接着剤層には、ポリウレタンポリウレア樹脂(A)とエポキシ樹脂(B)との反応や、エポキシ樹脂(B)の単独での反応を促進させる目的で、硬化促進剤、硬化剤を含有させることができる。エポキシ樹脂(B)の硬化促進剤としては、3級アミン化合物、ホスフィン化合物、イミダゾール化合物等が使用でき、硬化剤としては、ジシアンジアミド、カルボン酸ヒドラジド、酸無水物等が使用できる。 For the purpose of accelerating the reaction between the polyurethane polyurea resin (A) and the epoxy resin (B) or the reaction of the epoxy resin (B) alone, the curable conductive adhesive layer contains a curing accelerator and a curing agent. It can be included. As the curing accelerator for the epoxy resin (B), tertiary amine compounds, phosphine compounds, imidazole compounds and the like can be used, and as the curing agent, dicyandiamide, carboxylic acid hydrazide, acid anhydrides and the like can be used.
硬化促進剤のうち、3級アミン化合物としては、トリエチルアミン、ベンジルジメチルアミン、1,8−ジアザビシクロ(5.4.0)ウンデセン−7、1,5−ジアザビシクロ(4.3.0)ノネン−5等が挙げられる。また、ホスフィン化合物としては、トリフェニルホスフィン、トリブチルホスフィン等が挙げられる。また、イミダゾール化合物としては、2−メチルイミダゾール、2−エチル−4−メチルイミダゾール、2−フェニル−4−メチルイミダゾール、2,4−ジメチルイミダゾール、2−フェニルイミダゾール等のイミダゾール化合物が挙げられ、更にはイミダゾール化合物とエポキシ樹脂を反応させて溶剤に不溶化したタイプ、またはイミダゾール化合物をマイクロカプセルに封入したタイプ等の保存安定性を改良した潜在性硬化促進剤が挙げられるが、これらの中でも、潜在性硬化促進剤が好ましい。 Among the curing accelerators, the tertiary amine compounds include triethylamine, benzyldimethylamine, 1,8-diazabicyclo (5.4.0) undecene-7, 1,5-diazabicyclo (4.3.0) nonene-5. Etc. Examples of the phosphine compound include triphenylphosphine and tributylphosphine. Examples of imidazole compounds include imidazole compounds such as 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenyl-4-methylimidazole, 2,4-dimethylimidazole, and 2-phenylimidazole. There are latent curing accelerators with improved storage stability, such as a type in which an imidazole compound and an epoxy resin are reacted to insolubilize in a solvent, or a type in which an imidazole compound is encapsulated in a microcapsule. A curing accelerator is preferred.
硬化剤としてのカルボン酸ヒドラジドとしては、コハク酸ヒドラジド、アジピン酸ヒドラジド等が挙げられる。また、酸無水物としては、無水ヘキサヒドロフタル酸、無水トリメリット酸等が挙げられる。 Examples of the carboxylic acid hydrazide as the curing agent include succinic acid hydrazide and adipic acid hydrazide. Examples of the acid anhydride include hexahydrophthalic anhydride and trimellitic anhydride.
これらの硬化促進剤または硬化剤としては、それぞれ2種類以上を併用してもよく、その使用量は合計で(硬化促進剤または硬化剤のどちらか一方のみを使用する場合も含まれる)、エポキシ樹脂(B)100重量部に対して0.1〜30重量部の範囲であることが好ましい。 As these curing accelerators or curing agents, two or more types may be used in combination, respectively, and the total amount used (including the case where only one of the curing accelerator or the curing agent is used) is an epoxy. It is preferably in the range of 0.1 to 30 parts by weight with respect to 100 parts by weight of the resin (B).
また、硬化性導電性接着剤層には、導電性、接着性、耐ハンダリフロー性を劣化させない範囲で、シランカップリング剤、酸化防止剤、顔料、染料、粘着付与樹脂、可塑剤、紫外線吸収剤、消泡剤、レベリング調整剤,充填剤,難燃剤等を添加してもよい。 In addition, the curable conductive adhesive layer has silane coupling agents, antioxidants, pigments, dyes, tackifier resins, plasticizers, UV absorbers, as long as the conductivity, adhesiveness, and solder reflow resistance are not deteriorated. Agents, antifoaming agents, leveling regulators, fillers, flame retardants and the like may be added.
続いて、本発明で用いる硬化性を有しない絶縁フィルムについて説明する。
絶縁層は、硬化性電磁波シールド性接着フィルムに機械的強度を与える役割を担う。即ち、特許文献4における基材フィルムに当たる。
Then, the insulating film which does not have curability used by this invention is demonstrated.
The insulating layer plays a role of giving mechanical strength to the curable electromagnetic wave shielding adhesive film. That is, it corresponds to the base film in Patent Document 4.
硬化性を有しない絶縁フィルムとしては、ポリエステル、ポリイミド、ポリアミドイミド、ポリエーテルイミド、ポリエチレンサルファイド、ポリサルフォン、ポリフェニレンサルファイドなどの各種プラスチックフィルムの事を示す。
硬化性を有しない絶縁フィルムは、耐熱性、屈曲性、難燃性などを考慮した材料を使用することが好ましい。また、硬化性を有しない絶縁フィルムの厚みは、0.5μm〜50μmであることが好ましく、2μm〜30μmであることがより好ましい。絶縁層の厚さが0.5μm未満の場合には、フィルム強度が低下し、導電性接着剤層の絶縁性支持体としての役割を担うことが難しい。一方で、50μmを超える場合には、電磁波シールド性接着性フィルムの被着体面の凹凸への追従性が低下し、十分なシールド効果が得られなくなるのと共に、十分な屈曲性が得られない。
Examples of the non-curable insulating film include various plastic films such as polyester, polyimide, polyamideimide, polyetherimide, polyethylene sulfide, polysulfone, and polyphenylene sulfide.
For the insulating film having no curability, it is preferable to use a material in consideration of heat resistance, flexibility, flame retardancy, and the like. Moreover, it is preferable that the thickness of the insulating film which does not have curability is 0.5 micrometer-50 micrometers, and it is more preferable that it is 2 micrometers-30 micrometers. When the thickness of the insulating layer is less than 0.5 μm, the film strength is lowered, and it is difficult to play a role as an insulating support for the conductive adhesive layer. On the other hand, if the thickness exceeds 50 μm, the followability of the electromagnetic wave shielding adhesive film to the unevenness of the adherend surface decreases, and a sufficient shielding effect cannot be obtained, and sufficient flexibility cannot be obtained.
さらに導電性接着剤層と同様に、硬化性を有しない絶縁フィルムには、耐熱性や耐屈曲性等の性能を損なわない範囲で、フェノール系樹脂、シリコーン系樹脂、ユリア系樹脂、アクリル系樹脂、ポリエステル系樹脂、ポリアミド系樹脂、ポリイミド系樹脂などを含有させることができる。 Furthermore, as with the conductive adhesive layer, the insulating film having no curability has a phenolic resin, a silicone resin, a urea resin, an acrylic resin as long as it does not impair the performance such as heat resistance and bending resistance. , Polyester resins, polyamide resins, polyimide resins, and the like.
また、硬化性を有しない絶縁フィルムには、導電性接着剤層の場合と同様に、接着性、耐ハンダリフロー性を劣化させない範囲で、シランカップリング剤、酸化防止剤、顔料、染料、粘着付与樹脂、可塑剤、紫外線吸収剤、消泡剤、レベリング調整剤,充填剤,難燃剤等を添加してもよい。 In addition, as in the case of the conductive adhesive layer, the insulating film having no curability has a silane coupling agent, an antioxidant, a pigment, a dye, an adhesive, and the like within a range that does not deteriorate the adhesiveness and solder reflow resistance. An imparting resin, a plasticizer, an ultraviolet absorber, an antifoaming agent, a leveling regulator, a filler, a flame retardant and the like may be added.
続いて、2つの導電層のうちの1つ、導電性被膜について説明する。
導電性被膜は、電磁波シールド性機能を担う層であり、前述の硬化性導電性接着剤層とは異なり、硬化性を有しない。導電性被膜は、導電性粒子が保護物質によって被覆されてなる平均粒子径が0.001〜0.5μmの被覆導電性粒子を含む分散体から形成された被膜である。
Subsequently, one of the two conductive layers, the conductive film, will be described.
The conductive film is a layer having an electromagnetic wave shielding function, and has no curability unlike the above-described curable conductive adhesive layer. The conductive coating is a coating formed from a dispersion containing coated conductive particles having an average particle diameter of 0.001 to 0.5 μm formed by coating conductive particles with a protective substance.
被覆導電性粒子の分散体に含まれる導電性粒子は、得られる導電性被膜に導電性を付与するためのものである。
このような導電性粒子としては、代表的なものとして導電性の金属物質が挙げられる。例えば、金、銀、銅、ニッケル、白金、パラジウム、鉄、コバルト、タングステン、チタン、インジウム、イリジウム、ロジウム、アモルファス銅等の金属や、例えば、銀−銅合金等の合金、銀−銅複合体等の金属複合体、銀めっき銅等の金属をさらに他の金属で被覆したもの等が挙げられる。なかでも、金、銀、銅、ニッケル、白金、パラジウム、鉄が好ましく、更に、金、銀、銅、ニッケルが好ましく、更に、導電性、コストの点で銀が好ましい。また、その他の導電性粒子としては、例えば、上記金属で被覆した無機物粉末、酸化銀、酸化インジウム、酸化アンチモン、酸化亜鉛、酸化スズ、アンチモンドープ酸化スズ、インジウム−スズ複合酸化物等の金属酸化物、またはカーボンブラック、グラファイト等を用いることもできる。導電性粒子は、1種を単独で用いても、2種類以上を組み合わせて用いてもよい。
The conductive particles contained in the dispersion of the coated conductive particles are for imparting conductivity to the obtained conductive film.
Typical examples of such conductive particles include conductive metal substances. For example, gold, silver, copper, nickel, platinum, palladium, iron, cobalt, tungsten, titanium, indium, iridium, rhodium, amorphous copper and other metals, for example, alloys such as silver-copper alloys, silver-copper composites Metal composites such as those coated with other metals such as silver-plated copper. Of these, gold, silver, copper, nickel, platinum, palladium, and iron are preferable, gold, silver, copper, and nickel are more preferable, and silver is more preferable in terms of conductivity and cost. Examples of other conductive particles include metal powders such as inorganic powders coated with the above metals, silver oxide, indium oxide, antimony oxide, zinc oxide, tin oxide, antimony-doped tin oxide, and indium-tin composite oxide. Or carbon black, graphite or the like can also be used. As the conductive particles, one kind may be used alone, or two or more kinds may be used in combination.
本発明の電磁波シールド性接着性フィルムを構成する導電性被膜の表面抵抗率は、1×10−3〜5×10−1(Ω/□)であることが好ましく、より好ましくは1×10−2〜3×10−1(Ω/□)である。導電性被膜の表面抵抗率が1×10−3(Ω/□)よりも小さいと、導電性微粒子自身の抵抗率に近くなり、被膜中に占める微粒子の密度が高くなり、屈曲性が悪くなる為好ましくない。また、5×10−1(Ω/□)よりも大きい場合、十分な電磁波シールド性が悪くなる為好ましくない。 The surface resistivity of the conductive film constituting the electromagnetic wave shielding adhesive film of the present invention is preferably 1 × 10 −3 to 5 × 10 −1 (Ω / □), more preferably 1 × 10 −. 2 to 3 × 10 −1 (Ω / □). When the surface resistivity of the conductive coating is smaller than 1 × 10 −3 (Ω / □), the resistivity is close to the resistivity of the conductive fine particles themselves, the density of the fine particles in the coating is increased, and the flexibility is deteriorated. Therefore, it is not preferable. Moreover, when larger than 5 * 10 < -1 > (ohm / square), since sufficient electromagnetic wave shielding property worsens, it is unpreferable.
さらに、本発明で用いられる導電性被膜の厚みは、0.001〜20μmであることが好ましく、0.05〜10μmであることがより好ましい。導電性被膜の厚みが0.001μmよりも薄いと、被膜の強度が弱く、十分なシールド性が得られないため好ましくない。一方、導電性被膜の厚みが20μmよりも厚いと、被膜の屈曲性が損なわれる恐れがあるため好ましくない。 Furthermore, the thickness of the conductive coating used in the present invention is preferably 0.001 to 20 μm, and more preferably 0.05 to 10 μm. If the thickness of the conductive coating is less than 0.001 μm, the strength of the coating is weak and sufficient shielding properties cannot be obtained, which is not preferable. On the other hand, if the thickness of the conductive coating is greater than 20 μm, the flexibility of the coating may be impaired, such being undesirable.
導電性被膜の形成に用いられる被覆導電性粒子を含む分散体について説明する。
被覆導電性粒子を含む分散体中の被覆導電性粒子の平均粒子径は、0.001〜0.5μmであり、0.001〜0.3μmであることが好ましい。本発明では、導電性粒子の少なくとも一部が保護物質によって被覆されていればよい。
導電性被膜の形成に用いられる被覆導電性粒子の大きさは、例えば、レーザー解析法微粒子径測定装置(コールター社製ナノサイザー)や、透過型電子顕微鏡(日本電子株式会社)により測定された数平均粒子径が、0.001〜0.5μmであり、0.001〜0.3μmであることが好ましい。被覆導電性粒子の平均粒子径が0.5μmよりも大きいと、低温で導電性を発現しにくくなるので好ましくない。また、平均粒子径が0.001μmよりも小さい場合、被覆導電性粒子分散体の安定性が損なわれるため好ましくない。
The dispersion containing the coated conductive particles used for forming the conductive film will be described.
The average particle diameter of the coated conductive particles in the dispersion containing the coated conductive particles is 0.001 to 0.5 μm, and preferably 0.001 to 0.3 μm. In the present invention, it is sufficient that at least a part of the conductive particles is covered with a protective substance.
The size of the coated conductive particles used for forming the conductive coating is, for example, a number average measured by a laser analysis fine particle size measuring device (Norcizer manufactured by Coulter, Inc.) or a transmission electron microscope (JEOL Ltd.). The particle diameter is 0.001 to 0.5 μm, preferably 0.001 to 0.3 μm. If the average particle diameter of the coated conductive particles is larger than 0.5 μm, it is difficult to develop conductivity at low temperatures, which is not preferable. Moreover, when the average particle diameter is smaller than 0.001 μm, the stability of the coated conductive particle dispersion is impaired, which is not preferable.
被覆導電性粒子の分散体は、例えば下記(1)〜(3)に挙げるような方法で得ることができ、これら方法は適宜選択することができるが、(1)の方法で得ることが好ましい。
(1)還元により保護物質と導電性粒子とに分離する機能を有する金属塩(例えば、カルボン酸金属塩など)に対し、還元剤、熱、超音波、紫外線等を作用させ、金属塩を還元することにより、導電性粒子が保護物質で被覆されてなる被覆導電性粒子の分散体を得る。
(2)導電性粒子と保護物質とを乾式法または湿式法で混合して、導電性粒子が保護物質により被覆されてなる被覆導電性粒子を得、湿式法の場合はそのまま分散体としたり、乾式法の場合は任意の分散媒に被覆導電性粒子を分散し、分散体を得る。
(3)保護物質を含む溶液中に、導電性粒子を投入することで、導電性粒子を保護物質により被覆してなる被覆導電性粒子の分散体を得る。
The dispersion of the coated conductive particles can be obtained, for example, by the methods listed in the following (1) to (3), and these methods can be appropriately selected, but are preferably obtained by the method (1). .
(1) A metal salt (for example, a carboxylic acid metal salt) having a function of separating into a protective substance and conductive particles by reduction is reacted with a reducing agent, heat, ultrasonic waves, ultraviolet rays, etc. to reduce the metal salt. By doing so, a dispersion of coated conductive particles in which the conductive particles are coated with a protective substance is obtained.
(2) Conductive particles and a protective substance are mixed by a dry method or a wet method to obtain coated conductive particles in which the conductive particles are coated with a protective material. In the case of the dry method, the coated conductive particles are dispersed in an arbitrary dispersion medium to obtain a dispersion.
(3) By introducing conductive particles into a solution containing a protective substance, a dispersion of coated conductive particles obtained by coating the conductive particles with a protective substance is obtained.
被覆導電性粒子の分散体において、保護物質は、導電性粒子の凝集を防ぎ、分散安定性を維持するために必要なものであり、導電性粒子に対する親和性基を化合物中に1個または複数個有する化合物を使用することが好ましい。 In the dispersion of coated conductive particles, the protective substance is necessary for preventing aggregation of the conductive particles and maintaining the dispersion stability. One or more affinity groups for the conductive particles are contained in the compound. It is preferable to use a compound having one.
前記親和性基としては、イオン性官能基を挙げることができる。
イオン性官能基としては、陰イオン性官能基もしくは陽イオン性官能基が挙げられる。
Examples of the affinity group include ionic functional groups.
Examples of the ionic functional group include an anionic functional group and a cationic functional group.
陰イオン性官能基としては、例えば、カルボキシル基、スルホン酸基、リン酸基、水酸基、シアノ基、リン酸エステル基等が挙げられ、カルボキシル基、スルホン酸基およびリン酸基からなる群から選択される1種以上の官能基が好ましい。本発明においては、低温かつ短時間での加熱により良好な導電性を示す導電性被膜の形成が可能になるため、保護物質としてカルボキシル基を有するものが好ましい。 Examples of the anionic functional group include a carboxyl group, a sulfonic acid group, a phosphoric acid group, a hydroxyl group, a cyano group, and a phosphate ester group, and are selected from the group consisting of a carboxyl group, a sulfonic acid group, and a phosphoric acid group. One or more functional groups are preferred. In the present invention, it is possible to form a conductive film exhibiting good conductivity by heating at a low temperature for a short time, so that a protective substance having a carboxyl group is preferable.
陽イオン性官能基としては、例えば、窒素原子および/または硫黄原子を含んでいることが好ましく、例えば、塩基性基として存在していることが好ましい。前記塩基性基としては、例えば、アミノ基、アミド基、メルカプト基、スルフィド基、スルフェニル基、スルファジイル基等が挙げられる。 The cationic functional group preferably contains, for example, a nitrogen atom and / or a sulfur atom, and preferably, for example, exists as a basic group. Examples of the basic group include an amino group, an amide group, a mercapto group, a sulfide group, a sulfenyl group, and a sulfadiyl group.
イオン性官能基を有する保護物質の分子量に特に制限はなく、重量平均分子量1000未満の低分子量化合物も重量平均分子量1000以上の高分子量の樹脂であってもよい。高分子量の樹脂の場合、重量平均分子量は100000未満であることが好ましい。また、高分子量の樹脂の場合、前記のイオン性官能基は、主鎖に含まれていても、側鎖もしくは側鎖と主鎖の双方に含まれていても良い。 The molecular weight of the protective substance having an ionic functional group is not particularly limited, and a low molecular weight compound having a weight average molecular weight of less than 1000 may be a high molecular weight resin having a weight average molecular weight of 1000 or more. In the case of a high molecular weight resin, the weight average molecular weight is preferably less than 100,000. In the case of a high molecular weight resin, the ionic functional group may be contained in the main chain, or may be contained in the side chain or both the side chain and the main chain.
保護物質のうち、陰イオン性官能基を有する化合物の1つ、カルボキシル基を有する化合物として、カルボキシル基を有する有機酸を以下に例示する。
カルボキシル基を有する有機酸としては、例えば、飽和カルボン酸、不飽和カルボン酸、ジカルボン酸、ヒドロキシカルボン酸、芳香族カルボン酸等を挙げることができる。
Among the protective substances, one of the compounds having an anionic functional group, an organic acid having a carboxyl group, is exemplified below as a compound having a carboxyl group.
Examples of the organic acid having a carboxyl group include saturated carboxylic acids, unsaturated carboxylic acids, dicarboxylic acids, hydroxycarboxylic acids, and aromatic carboxylic acids.
飽和カルボン酸としては、例えば、直鎖飽和カルボン酸として、プロピオン酸、酪酸、吉草酸(別名:ペンタン酸)、カプロン酸(別名:ヘキサン酸)、エナント酸、カプリル酸、ペラルゴン酸、カプリン酸、ウンデシル酸、ラウリン酸、トリデシル酸、ミリスチン酸、ペンタデシル酸、パルミチン酸、ヘプタデカン酸、ステアリン酸、ノナデカン酸、アラキジン酸、ベヘン酸、リグノセリン酸、セロチン酸、ヘプタコサン酸、モンタン酸、メリシン酸、ラクセル酸等が挙げられ、分岐飽和カルボン酸としては、例えば、イソ酪酸、イソ吉草酸、2‐エチルヘキサン酸、2‐エチルイソヘキサン酸、2‐プロピルヘプタン酸、2‐ブチルオクタン酸、2‐イソブチルイソオクタン酸、2‐ペンチルノナン酸、2‐イソペンチルノナン酸、2‐ヘキシルデカン酸、2‐ヘキシルイソデカン酸、2‐ブチルドデカン酸、2‐イソブチルドデカン酸、2‐ヘプチルウンデカン酸、2‐イソヘプチルウンデカン酸、2‐イソペプチルイソウンデカン酸、2‐ドデシルヘキサン酸、2‐イソドデシルヘキサン酸、2‐オクチルドデカン酸、2‐イソオクチルドデカン酸、2‐オクチルイソドデカン酸、2‐ノニルトリデカン酸、2‐イソノニルイソトリデカン酸、2‐デシルドデカン酸、2‐イソデシルドデカン酸、2‐デシルイソドデカン酸、2‐デシルテトラデカン酸、2‐オクチルヘキサデカン酸、2‐イソオクチルヘキサデカン酸、2‐ウンデシルペンタデカン酸、2‐イソウンデシルペンタデカン酸、2‐ドデシルヘプタデカン酸、2‐イソドデシルイソヘプタデカン酸、2‐デシルオクタデカン酸、2‐デシルイソオクタデカン酸、2‐トリデシルヘプタデカン酸、2‐イソトリデシルイソヘプタデカン酸、2‐テトラデシルオクタデカン酸、2‐イソテトラデシルオクタデカン酸、2‐ヘキサデシルヘキサデカン酸、2‐ヘキサデシルテトラデカン酸、2‐ヘキサデシルイソヘキサデカン酸、2‐イソヘキサデシルイソヘキサデカン酸、2‐ペンタデシルノナデカン酸、2‐イソペンタデシルイソノナデカン酸、2‐テトラデシルベヘン酸、2‐イソテトラデシルベヘン酸、2‐テトラデシルイソベヘン酸、2‐イソテトラデシルイソベヘン酸、イソヘプタン酸、イソミリスチン酸、イソパルミチン酸、イソステアリン酸、イソアラキン酸等が挙げられ、三級カルボン酸としては、例えば、ピバリン酸、ネオノナン酸、ネオデカン酸などが挙げられる。中でも、安定性や低温分解性を考慮するとカプロン酸、エナント酸、カプリル酸、ミリスチン酸、オレイン酸、ステアリン酸等が好ましい。 As the saturated carboxylic acid, for example, as a linear saturated carboxylic acid, propionic acid, butyric acid, valeric acid (also known as pentanoic acid), caproic acid (also known as hexanoic acid), enanthic acid, caprylic acid, pelargonic acid, capric acid, Undecylic acid, lauric acid, tridecylic acid, myristic acid, pentadecylic acid, palmitic acid, heptadecanoic acid, stearic acid, nonadecanoic acid, arachidic acid, behenic acid, lignoceric acid, serotic acid, heptacosanoic acid, montanic acid, melicic acid, laxelic acid Examples of branched saturated carboxylic acids include isobutyric acid, isovaleric acid, 2-ethylhexanoic acid, 2-ethylisohexanoic acid, 2-propylheptanoic acid, 2-butyloctanoic acid, and 2-isobutylisooctane. Acid, 2-pentylnonanoic acid, 2-isopentylnonanoic acid, 2- Xyldecanoic acid, 2-hexylisodecanoic acid, 2-butyldodecanoic acid, 2-isobutyldodecanoic acid, 2-heptylundecanoic acid, 2-isoheptylundecanoic acid, 2-isopeptylisoundecanoic acid, 2-dodecylhexanoic acid, 2-Isododecylhexanoic acid, 2-octyldodecanoic acid, 2-isooctyldodecanoic acid, 2-octylisododecanoic acid, 2-nonyltridecanoic acid, 2-isononylisotridecanoic acid, 2-decyldodecanoic acid, 2- Isodecyldodecanoic acid, 2-decylisododecanoic acid, 2-decyltetradecanoic acid, 2-octylhexadecanoic acid, 2-isooctylhexadecanoic acid, 2-undecylpentadecanoic acid, 2-isoundecylpentadecanoic acid, 2-dodecylhepta Decanoic acid, 2-isododecylisoheptadecanoic acid, 2-deci Octadecanoic acid, 2-decylisooctadecanoic acid, 2-tridecylheptadecanoic acid, 2-isotridecylisoheptadecanoic acid, 2-tetradecyloctadecanoic acid, 2-isotetradecyloctadecanoic acid, 2-hexadecylhexadecanoic acid, 2-hexadecyltetradecanoic acid, 2-hexadecylisohexadecanoic acid, 2-isohexadecylisohexadecanoic acid, 2-pentadecylnonadecanoic acid, 2-isopentadecylisononadecanoic acid, 2-tetradecylbehenic acid, 2 -Isotetradecyl behenic acid, 2-tetradecylisobehenic acid, 2-isotetradecylisobehenic acid, isoheptanoic acid, isomyristic acid, isopalmitic acid, isostearic acid, isoarachidic acid, etc. Is, for example, pivalic acid, neononanoic acid, And neodecanoic acid. Of these, caproic acid, enanthic acid, caprylic acid, myristic acid, oleic acid, stearic acid and the like are preferable in consideration of stability and low-temperature decomposability.
不飽和カルボン酸としては、例えば、アクリル酸、クロトン酸、イソクロトン酸、ウンデシレン酸、オレイン酸、エライジン酸、セトレイン酸、エルカ酸、ブラシジン酸、ソルビン酸、リノール酸、リノレン酸、アラキドン酸、プロピオール酸、ステアロール酸等が挙げられる。 Examples of unsaturated carboxylic acids include acrylic acid, crotonic acid, isocrotonic acid, undecylenic acid, oleic acid, elaidic acid, celetic acid, erucic acid, brassic acid, sorbic acid, linoleic acid, linolenic acid, arachidonic acid, propiolic acid , Stearolic acid and the like.
ジカルボン酸、としては、例えば、シュウ酸、マロン酸、コハク酸、グルタル酸、アジピン酸、ピメリン酸、スベリン酸、アゼライン酸、セバシン酸、イタコン酸、フマル酸、マレイン酸、シトラコン酸、メサコン酸等が挙げられる。 Examples of the dicarboxylic acid include oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, itaconic acid, fumaric acid, maleic acid, citraconic acid, and mesaconic acid. Is mentioned.
ヒドロキシカルボン酸としては、例えば、乳酸、リンゴ酸、クエン酸、ヒドロキシ酪酸、酒石酸、シトラマル酸、クエン酸、イソクエン酸、サリチル酸、クマル酸等が挙げられる。 Examples of the hydroxycarboxylic acid include lactic acid, malic acid, citric acid, hydroxybutyric acid, tartaric acid, citramalic acid, citric acid, isocitric acid, salicylic acid, and coumaric acid.
芳香族カルボン酸としては、例えば、安息香酸、フタル酸、イソフタル酸、テレフタル酸、サリチル酸、没食子酸、メリト酸、ケイ皮酸等が挙げられる。 Examples of the aromatic carboxylic acid include benzoic acid, phthalic acid, isophthalic acid, terephthalic acid, salicylic acid, gallic acid, mellitic acid, and cinnamic acid.
これらのカルボン酸は、低温での導電発現性の観点から、炭素数3〜22のものが好ましく用いられる。また、1種類を単独で使用しても、2種類以上を組み合わせて使用してもよい。 As these carboxylic acids, those having 3 to 22 carbon atoms are preferably used from the viewpoint of electrical conductivity at low temperatures. Moreover, you may use individually by 1 type or in combination of 2 or more types.
保護物質のうち、陽イオン性官能基を有する化合物の1つ、アミノ基を有する化合物としては、例えば、ブチルアミン、オクチルアミン、ドデシルアミン、オクタデシルアミン、オレイルアミン、ラウリルアミン、及びステアリルアミン等の第一級アミン、ジココアミン、ジ水素化タロウアミン、及びジステアリルアミン等の第二級アミン、ドデシルジメチルアミン、オクタデシルジメチルアミン、及びトリオクチルアミン等の第三級アミン、第四級アミン塩等のアルキルアミン、ステアリルプロピレンジアミン、オクタメチレンジアミン等のジアミン、 2-メチルアミノエタノール、ジエタノールアミン、ブトキシプロピルアミン、ジエチルメチルアミン、2-ジメチルアミノエタノール、メチルジエタノールアミン等のアルカノールアミンが挙げられる。 Among the protective substances, one of the compounds having a cationic functional group and the compound having an amino group include, for example, first compounds such as butylamine, octylamine, dodecylamine, octadecylamine, oleylamine, laurylamine, and stearylamine. Secondary amines such as tertiary amines, dicocoamines, dihydrogenated tallow amines, and distearylamines, tertiary amines such as dodecyldimethylamine, octadecyldimethylamine, and trioctylamine, alkylamines such as quaternary amine salts, Diamines such as stearylpropylenediamine and octamethylenediamine, alkanolamines such as 2-methylaminoethanol, diethanolamine, butoxypropylamine, diethylmethylamine, 2-dimethylaminoethanol, methyldiethanolamine Is mentioned.
保護物質のうち、陽イオン性官能基を有する化合物の1つ、アミド基を有する化合物としては、例えば、カルボン酸アミド、アミノカルボン酸塩が挙げられる。 Among the protective substances, one of the compounds having a cationic functional group and the compound having an amide group include, for example, carboxylic acid amides and aminocarboxylates.
保護物質のうち、陽イオン性官能基を有する化合物の1つ、メルカプト基含有化合物としては、例えば、メルカプト酢酸、メルカプトプロピオン酸、チオジプロピオン酸、メルカプトコハク酸、チオ酢酸等の酸チオール類、エチルメルカプタン、プロピルメルカプタン、イソプロピルメルカプタン、n−ブチルメルカプタン、アリルメルカプタン、ジメチルメルカプタン、メルカプトエタノール、アミノエチルメルカプタン、チオジエチルアミン等の脂肪族チオール類、シクロヘキシルチオール等の脂環式チオール類、チオフェノール等の芳香族チオール類、チオジエチレングリコール、チオジグリコール酸、エチレンチオグリコール等のチオグリコール類等が挙げられる。 Among the protective substances, one of the compounds having a cationic functional group, a mercapto group-containing compound, for example, acid thiols such as mercaptoacetic acid, mercaptopropionic acid, thiodipropionic acid, mercaptosuccinic acid, thioacetic acid, Aliphatic thiols such as ethyl mercaptan, propyl mercaptan, isopropyl mercaptan, n-butyl mercaptan, allyl mercaptan, dimethyl mercaptan, mercaptoethanol, aminoethyl mercaptan, thiodiethylamine, alicyclic thiols such as cyclohexylthiol, thiophenol, etc. Examples include aromatic thiols, thioglycols such as thiodiethylene glycol, thiodiglycolic acid, and ethylenethioglycol.
保護物質のうち、陽イオン性官能基を有する化合物の1つ、スルフィド化合物として、例えば、ジメチルスルフィド、ジエチルスルフィド、メチルプロピルスルフィド等が挙げられる。 Among the protective substances, one of the compounds having a cationic functional group and the sulfide compound include, for example, dimethyl sulfide, diethyl sulfide, methylpropyl sulfide and the like.
保護物質のうち、イオン性官能基を有する保護物質としては、前記した化合物以外にも、顔料分散剤、界面活性剤、カップリング剤として一般に市販されている化合物も使用することができる。これらは、単独で用いても、複数の形態の化合物を併用してもよい。 Among the protective substances, as the protective substance having an ionic functional group, in addition to the above-mentioned compounds, compounds generally marketed as pigment dispersants, surfactants, and coupling agents can also be used. These may be used alone or in combination with a plurality of forms of compounds.
前記顔料分散剤は、上述した親和性基を化合物中に1個以上有するものが好ましく、例えば、ポリエーテル類、ポリウレタン樹脂、(不飽和)ポリエステル樹脂、アルキッド樹脂、ブチラール樹脂、アセタール樹脂、ポリアミド樹脂、(メタ)アクリル樹脂、スチレン/(メタ)アクリル樹脂、ポリスチレン樹脂、ニトロセルロース、ベンジルセルロース、セルロース(トリ)アセテート、カゼイン、シェラック、ゼラチン、ギルソナイト、ロジン、ロジンエステル、ポリビニルアルコール、ポリビニルピロリドン、ポリアクリルアミド、ヒドロキシエチルセルロース、ヒドロキシプロピルセルロース、メチルセルロース、エチルセルロース、ヒドロキシエチルメチルセルロース、ヒドロキシプロピルメチルセルロース、カルボキシメチルセルロース、カルボキシメチルエチルセルロース、カルボキシメチルニトロセルロース、エチレン/ビニルアルコール樹脂、スチレン/無水マレイン酸樹脂、ポリブタジエン樹脂、ポリ塩化ビニル樹脂、ポリ塩化ビニリデン樹脂、ポリフッ化ビニリデン樹脂、ポリ酢酸ビニル樹脂、エチレン/酢酸ビニル樹脂、塩化ビニル/酢酸ビニル樹脂、塩化ビニル/酢酸ビニル/マレイン酸樹脂、フッ素樹脂、シリコン樹脂、エポキシ樹脂、フェノキシ樹脂、フェノール樹脂、マレイン酸樹脂、尿素樹脂、メラミン樹脂、ベンゾグアナミン樹脂、ケトン樹脂、石油樹脂、塩素化ポリオレフィン樹脂、変性塩素化ポリオレフィン樹脂、塩素化ポリウレタン樹脂等が挙げられ、イオン交換層に対応する性質を有するものを適宜選択することができる。また、これらは必要に応じて、親和性基を導入するために変性されていても良い。 The pigment dispersant preferably has one or more of the above-mentioned affinity groups in the compound. For example, polyethers, polyurethane resins, (unsaturated) polyester resins, alkyd resins, butyral resins, acetal resins, polyamide resins , (Meth) acrylic resin, styrene / (meth) acrylic resin, polystyrene resin, nitrocellulose, benzylcellulose, cellulose (tri) acetate, casein, shellac, gelatin, gilsonite, rosin, rosin ester, polyvinyl alcohol, polyvinylpyrrolidone, poly Acrylamide, hydroxyethylcellulose, hydroxypropylcellulose, methylcellulose, ethylcellulose, hydroxyethylmethylcellulose, hydroxypropylmethylcellulose, carboxymethylcellulose Loose, carboxymethyl ethyl cellulose, carboxymethyl nitrocellulose, ethylene / vinyl alcohol resin, styrene / maleic anhydride resin, polybutadiene resin, polyvinyl chloride resin, polyvinylidene chloride resin, polyvinylidene fluoride resin, polyvinyl acetate resin, ethylene / acetic acid Vinyl resin, vinyl chloride / vinyl acetate resin, vinyl chloride / vinyl acetate / maleic acid resin, fluorine resin, silicone resin, epoxy resin, phenoxy resin, phenol resin, maleic acid resin, urea resin, melamine resin, benzoguanamine resin, ketone resin Petroleum resins, chlorinated polyolefin resins, modified chlorinated polyolefin resins, chlorinated polyurethane resins, and the like, and those having properties corresponding to the ion exchange layer can be appropriately selected. These may be modified to introduce an affinity group, if necessary.
前記界面活性剤としては、特に限定されず、陰イオン系、非イオン系、両性イオン系、陽イオン系のものあるが、用途に応じて、これらのいずれのものをも用いることができる。 The surfactant is not particularly limited and may be an anionic, nonionic, zwitterionic, or cationic one, and any of these may be used depending on the application.
また、これらとは分類形態が異なるものとして、フッ素系界面活性剤、アリル系反応性界面活性剤等の反応性界面活性剤、カチオン性セルロース誘導体、ポリカルボン酸、ポリスチレンスルホン酸等の高分子界面活性剤が挙げられる。本発明ではこのような界面活性剤も含め、保護物質として用いることができる。
また界面活性剤は、1種類を単独で用いることも、また2種類以上を組み合わせて用いることもできる。
In addition, these are classified into different forms, such as reactive surfactants such as fluorosurfactants and allyl reactive surfactants, polymer interfaces such as cationic cellulose derivatives, polycarboxylic acids, and polystyrenesulfonic acids. An activator is mentioned. In the present invention, such a surfactant can be used as a protective substance.
Moreover, surfactant can be used individually by 1 type, and can also be used in combination of 2 or more type.
前記カップリング剤としては、一般に、シランカップリング剤、チタネート系カップリング剤、アルミニウム系カップリング剤、ジルコニウム系カップリング剤等を使用することができる。 As the coupling agent, generally, a silane coupling agent, a titanate coupling agent, an aluminum coupling agent, a zirconium coupling agent, or the like can be used.
本発明では、分散体の分散性や低温での導電発現性を考慮すると、保護物質としてはカルボキシル基を有する有機酸が好ましく、さらに、低温での導電発現性から、有機酸が、炭素数3〜22である、飽和または不飽和の、直鎖または分岐を有する、鎖状の脂肪酸であることが好ましい。 In the present invention, in consideration of the dispersibility of the dispersion and conductivity development at low temperature, the protective substance is preferably an organic acid having a carboxyl group. Further, from the viewpoint of conductivity development at low temperature, the organic acid has 3 carbon atoms. It is preferably a saturated or unsaturated, linear or branched chain fatty acid which is ˜22.
本発明において、保護物質は1種または2種以上を併用して用いてもよく、2種以上を使用する場合は、形態の異なる保護物質を併用することもできる。 In the present invention, the protective substances may be used alone or in combination of two or more kinds, and when two or more kinds are used, protective substances having different forms can be used in combination.
上記保護物質は、導電性粒子100重量部に対する保護物質の総量で0.1〜2000の範囲で用いることが好ましいが、1〜100重量部の範囲で用いることが更に好ましい。添加量が0.1重量部未満の場合、被覆導電性粒子の分散を安定に保つことが困難になり、導電性粒子が凝集する恐れがある。また、2000重量部を超える場合、導電性粒子の安定化に寄与しない余剰の保護物質の存在が、導電性被膜の導電性や、その他の物性に悪影響を与える恐れがある。 The protective substance is preferably used in the range of 0.1 to 2000 in terms of the total amount of the protective substance with respect to 100 parts by weight of the conductive particles, but more preferably in the range of 1 to 100 parts by weight. When the addition amount is less than 0.1 part by weight, it becomes difficult to keep the dispersion of the coated conductive particles stable, and the conductive particles may aggregate. On the other hand, when the amount exceeds 2000 parts by weight, the presence of an excessive protective substance that does not contribute to the stabilization of the conductive particles may adversely affect the conductivity of the conductive film and other physical properties.
被覆導電性粒子の分散体は、種々の方法で得ることができ、還元により保護物質と導電性粒子とに分離する機能を有する金属塩(例えば、カルボン酸金属塩など)に対し、還元剤、熱、超音波、紫外線等を作用させ、金属塩を還元することにより、導電性粒子が保護物質で被覆されてなる被覆導電性粒子の分散体を得ることが好ましい旨、前述した。還元剤を用いることが好ましい。
具体的には、液体媒体中、カルボキシル基を有する有機酸と金属の有機酸金属塩に対して、還元剤である下記一般式(1)で示されるカルボジヒドラジドまたは下記一般式(2)で示される多塩基酸ポリヒドラジドを等量以上用いて、前記有機酸金属塩を還元し、有機酸金属塩由来の有機酸が保護物質として、生成した導電性粒子を被覆、安定化してなる被覆導電性粒子の分散体を得ることができる。
前記方法は、還元反応が比較的低温、かつ迅速に進行するため、反応後の被覆導電性粒子の凝集が抑えられ、平均粒子径が小さく、かつ粒子径分布が狭い、被覆導電性粒子の分散体を得ることができる。この方法で得られる被覆導電性粒子の分散体は流動性や安定性に優れているため、低温かつ短時間の加熱により導電性の良好な導電性被膜を形成することができる。
The dispersion of the coated conductive particles can be obtained by various methods. For a metal salt having a function of separating into a protective substance and conductive particles by reduction (for example, a carboxylic acid metal salt), a reducing agent, As described above, it is preferable to obtain a dispersion of coated conductive particles in which conductive particles are coated with a protective substance by reducing the metal salt by applying heat, ultrasonic waves, ultraviolet rays, or the like. It is preferable to use a reducing agent.
Specifically, it is represented by a carbodihydrazide represented by the following general formula (1) or the following general formula (2) which is a reducing agent with respect to an organic acid and a metal organic acid metal salt having a carboxyl group in a liquid medium. Coated conductivity obtained by reducing the organic acid metal salt using an equal amount or more of the polybasic acid polyhydrazide, and coating and stabilizing the generated conductive particles using the organic acid derived from the organic acid metal salt as a protective substance. A dispersion of particles can be obtained.
In the above method, since the reduction reaction proceeds at a relatively low temperature and quickly, the aggregation of the coated conductive particles after the reaction is suppressed, the average particle size is small, and the particle size distribution is narrow. You can get a body. Since the dispersion of coated conductive particles obtained by this method is excellent in fluidity and stability, a conductive film having good conductivity can be formed by heating at a low temperature for a short time.
被覆導電性粒子の分散体の前記製造方法をより具体的に説明する。
例えば、金属化合物としてカルボン酸の金属塩の水溶液を用い、これをトルエンなどの水と相分離する非水系溶剤に混合する。この混合液に下記式(1)で示されるカルボジヒドラジド、または下記式(2)で示されるヒドラジド基を分子中に2つ以上有する多塩基酸ポリヒドラジドの水溶液を滴下して前記カルボン酸金属塩を還元する。還元により、有機酸金属塩由来の有機酸により導電性粒子を被覆してなる被覆導電性粒子が非水系溶剤に分散してなる分散体と水相との混合液が得る。次いで、前記混合液から水相を分離、除去した後、非水系溶剤相に新たな水を加え、不純物を水相に移行させ、水相を分離し、非水系溶剤相を洗浄し、有機酸金属塩由来の有機酸を保護物質とする、被覆導電性粒子を分散質、非水系溶剤を分散媒とする分散体が製造される。
The production method of the dispersion of coated conductive particles will be described more specifically.
For example, an aqueous solution of a metal salt of a carboxylic acid is used as the metal compound, and this is mixed with a non-aqueous solvent that phase separates from water such as toluene. An aqueous solution of a carbodihydrazide represented by the following formula (1) or a polybasic acid polyhydrazide having two or more hydrazide groups represented by the following formula (2) in the molecule is added dropwise to the mixed solution, and the carboxylic acid metal salt is added. To reduce. By reduction, a mixed liquid of a dispersion obtained by dispersing coated conductive particles obtained by coating conductive particles with an organic acid derived from an organic acid metal salt in a non-aqueous solvent and an aqueous phase is obtained. Next, after separating and removing the aqueous phase from the mixed solution, fresh water is added to the non-aqueous solvent phase, impurities are transferred to the aqueous phase, the aqueous phase is separated, the non-aqueous solvent phase is washed, and the organic acid A dispersion using a coated organic particle as a dispersoid and a non-aqueous solvent as a dispersion medium is produced using an organic acid derived from a metal salt as a protective substance.
上記式(2)で示されるヒドラジド基を分子中に2つ以上有する多塩基ポリヒドラジドとしては、例えば、二塩基酸ジヒドラジド、三塩基酸トリヒドラジド、四塩基酸テトラヒドラジド等が挙げられる。
二塩基酸ジヒドラジドとしては、例えば、シュウ酸ヒドラジド、マロン酸ジヒドラジド、コハク酸ジヒドラジド、グルタル酸ジヒドラジド、アジピン酸ジヒドラジド、セバチン酸ジヒドラジド、ドデカン酸ジヒドラジド、マレイン酸ジヒドラジド、フマル酸ジヒドラジド、イタコン酸ジヒドラジド、フタル酸ジヒドラジド、イソフタル酸ジヒドラジド、テレフタル酸ジヒドラジド、タルタロジヒドラジド、ピメリン酸ジヒドラジド、スベリン酸ジヒドラジド、アゼライン酸ジヒドラジド、ヘキサデカン酸ジヒドラジド、2,6−ナフトエ酸ジヒドラジド、1,4−ナフトエ酸ジヒドラジド、リンゴ酸ジヒドラジド、イミノジ酢酸ジヒドラジド、イタコン酸ジヒドラジド等が挙げられ、
三塩基酸トリヒドラジドとしては、例えば、クエン酸トリヒドラジド、トリメリット酸トリヒドラジド、ニトリロ酢酸トリヒドラジド、シクロヘキサントリカルボン酸トリヒドラジド等があげられる。
四塩基酸テトラヒドラジドとしては、例えば、エチレンジアミン四酢酸テトラヒドラジド、ピロメリット酸テトラヒドラジド等があげられる。
上記以外の多塩基酸ポリヒドラジドとしては、ポリアクリル酸ポリヒドラジド等が挙げられる。これらの多塩基酸ポリヒドラジドは、1種類を単独で、または2種類以上を組み合わせて用いることができる。
Examples of the polybasic polyhydrazide having two or more hydrazide groups represented by the formula (2) in the molecule include dibasic acid dihydrazide, tribasic acid trihydrazide, and tetrabasic acid tetrahydrazide.
Examples of the dibasic acid dihydrazide include oxalic acid hydrazide, malonic acid dihydrazide, succinic acid dihydrazide, glutaric acid dihydrazide, adipic acid dihydrazide, sebacic acid dihydrazide, dodecanoic acid dihydrazide, maleic acid dihydrazide, italic acid dihydrazide, Acid dihydrazide, isophthalic acid dihydrazide, terephthalic acid dihydrazide, tartarodihydrazide, pimelic acid dihydrazide, suberic acid dihydrazide, azelaic acid dihydrazide, hexadecanoic acid dihydrazide, 2,6-naphthoic acid dihydrazide, 1,4-naphthoic acid dihydrazide, apple dihydrazide Iminodiacetic acid dihydrazide, itaconic acid dihydrazide and the like,
Examples of the tribasic acid trihydrazide include citric acid trihydrazide, trimellitic acid trihydrazide, nitriloacetic acid trihydrazide, cyclohexanetricarboxylic acid trihydrazide, and the like.
Examples of the tetrabasic acid tetrahydrazide include ethylenediaminetetraacetic acid tetrahydrazide and pyromellitic acid tetrahydrazide.
Examples of polybasic acid polyhydrazides other than the above include polyacrylic acid polyhydrazide. These polybasic acid polyhydrazides can be used singly or in combination of two or more.
これら還元剤の添加量については、金属化合物の種類や濃度によっても異なるが、通常はすくなくとも金属化合物溶液から金属が還元析出するのに必要な化学量論比の量をしようすればよい。
前記した製造方法に好適に使用される還元剤は、ジヒドラジド、もしくはポリヒドラジド類であり、還元能を有する官能基を化合物中に2個以上有していることから、金属が還元析出するのに必要な化学量論比はヒドラジド基で換算して添加するのが好ましい。還元後に水相を除去する場合には、余剰の還元剤も同時に除去できるため、化学量論比以上の還元剤を使用しても良く、その上限は特に定められるものではないが、洗浄工程やコストを考えると、ヒドラジド換算の化学量論比で金属化合物を還元するのに必要な添加量の6倍以下であることが好ましい。
The amount of these reducing agents to be added varies depending on the type and concentration of the metal compound, but usually at least the stoichiometric ratio required for the metal to be reduced and deposited from the metal compound solution may be used.
The reducing agent preferably used in the above-described production method is dihydrazide or polyhydrazide, and since the compound has two or more functional groups having a reducing ability, the metal is reduced and precipitated. The required stoichiometric ratio is preferably added in terms of hydrazide groups. When removing the aqueous phase after the reduction, excess reducing agent can be removed at the same time, so a reducing agent with a stoichiometric ratio or more may be used, and the upper limit is not particularly defined. Considering the cost, it is preferably 6 times or less of the addition amount necessary for reducing the metal compound at a stoichiometric ratio in terms of hydrazide.
被覆導電性粒子の分散体に用いられる非水系溶剤を分散媒としては、特に限定されないが、例えば、ギ酸エチル、酢酸メチル、酢酸エチル、酢酸n−ブチル、酢酸(イソ)アミル、乳酸エチル、酢酸3−メトキシブチル、γ−ブチロラクトン、アセト酢酸エチル、エチルグリコールアセテート、エチルジグリコールアセテート(カルビトールアセテート)、ブチルジグリコールアセテート(ブチルカルビトールアセテート)、ジヒドロターピネニルアセテート、トリアセチン、二塩基酸エステル等のエステル系溶剤、アセトン、メチルエチルケトン、メチルイソブチルケトン、イソホロン、シクロヘキサノン、メチルシクロヘキサノン等のケトン系溶剤、プロピレングリコール、エチレングリコール、ジエチレングリコール、トリエチレングリコール等のグリコール系溶剤、エチレングリコールモノエチルエーテル、エチレングリコールモノブチルエーテル、ジエチレングリコールモノエチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、ジプロピレングリコールモノエチルエーテル、トリエチレングリコールモノメチルエーテル、トリプロピレングリコールモノエチルエーテル、ジエチレングリコールジメチルエーテル、ジプロピレングリコールジエチルエーテル等のグリコールエーテル系溶剤、n−ヘキサン、n−ヘプタン、n−オクタン、n−ノナン、n−デカン、n−ドデカン、ノルマルパラフィン系溶剤、イソパラフィン系溶剤、テレピン油、α−ピネン、β−ピネン、シクロパラフィン系溶剤、流動パラフィン、スチレンモノマー、リグロイン、ミネラルスピリット、石油エーテル、石油ベンジン等の脂肪族炭化水素系溶剤、ベンゼン、トルエン、キシレン、エチルベンゼン、ナフタレン、テトラリン、ソルベントナフサ等の芳香族炭化水素系溶剤、メタノール、エタノール、n−プロピルアルコール、イソプロピルアルコール、n−ブチルアルコール、ベンジルアルコール、シクロヘキサノール、3−メトキシブタノール、ソルミックス、4−ブタンジオール、オクタンジオール、グリセリン等や、ターピネオールC、α−ターピネオール、L−α−ターピネオール、ジヒドロターピネオール、パインオイルNT、テルソルブMTPH、ファインオキソコール140N、ファインオキソコール1600、ファインオキソコール180、ファインオキソコール180N、ファインオキソコール2000(日産化学工業株式会社製)等の高級アルコール等のアルコール系溶剤、ジオキサン、ジブチルエーテル等のエーテル系溶剤、テトラヒドロフラン、1,3−ジオキソラン等の環状エーテル、その他ジメチルカーボネート、エチルメチルカーボネート、ジ−n−ブチルカーボネート等を使用することができ、2種類以上を混合して使用することもできる。 The non-aqueous solvent used for the dispersion of the coated conductive particles is not particularly limited, and examples thereof include ethyl formate, methyl acetate, ethyl acetate, n-butyl acetate, (iso) amyl acetate, ethyl lactate, and acetic acid. 3-methoxybutyl, γ-butyrolactone, ethyl acetoacetate, ethyl glycol acetate, ethyl diglycol acetate (carbitol acetate), butyl diglycol acetate (butyl carbitol acetate), dihydroterpinenyl acetate, triacetin, dibasic acid ester Ester solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone, methyl cyclohexanone, and other ketone solvents, propylene glycol, ethylene glycol, diethylene glycol, triethylene glycol Glycol solvents such as coal, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, dipropylene glycol monoethyl ether, triethylene glycol monomethyl ether, tripropylene glycol Glycol ether solvents such as monoethyl ether, diethylene glycol dimethyl ether, dipropylene glycol diethyl ether, n-hexane, n-heptane, n-octane, n-nonane, n-decane, n-dodecane, normal paraffin solvent, isoparaffin solvent Solvent, turpentine oil, α-pinene, β-pinene, cycloparaffinic solvent, liquid paraffin, steel Monomers, ligroin, mineral spirits, aliphatic hydrocarbon solvents such as petroleum ether and petroleum benzine, aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, naphthalene, tetralin and solvent naphtha, methanol, ethanol, n- Propyl alcohol, isopropyl alcohol, n-butyl alcohol, benzyl alcohol, cyclohexanol, 3-methoxybutanol, solmix, 4-butanediol, octanediol, glycerin, terpineol C, α-terpineol, L-α-terpineol, Dihydroterpineol, pine oil NT, tersolve MTPH, fine oxocol 140N, fine oxocol 1600, fine oxocol 180, fine oxocol 80N, alcohol solvents such as higher alcohols such as Fine Oxocol 2000 (manufactured by Nissan Chemical Industries, Ltd.), ether solvents such as dioxane and dibutyl ether, cyclic ethers such as tetrahydrofuran and 1,3-dioxolane, other dimethyl carbonate, Ethyl methyl carbonate, di-n-butyl carbonate and the like can be used, and two or more kinds can be mixed and used.
上記非水系溶剤は、被覆導電性粒子の分散体100重量部中、通常0.01〜99重量部用いることが好ましく、0.1〜95重量部用いることがより好ましい。 The non-aqueous solvent is usually preferably used in an amount of 0.01 to 99 parts by weight, more preferably 0.1 to 95 parts by weight, in 100 parts by weight of the dispersion of coated conductive particles.
次に、被覆導電性粒子の分散体から導電性被膜を形成する一般的な方法について述べる。
保護物質は、分散体の状態では導電性粒子の表面を被覆し、導電性粒子の凝集を防ぎ、分散体としての分散安定性に寄与する。導電性被膜は、以下のような方法で導電性粒子から保護物質を剥がし、導電性粒子を加熱融着させることにより得ることができる。
(i) 分散体を対象に塗工後、加熱により保護物質を分解、揮発させることによって除去し、導電性粒子を加熱融着させることにより、導電性被膜を形成する。
(ii) 被覆導電性粒子の他に、保護物質のイオン性に対応するイオン交換能を有する物質を含む分散体を対象に塗工後、加熱により保護物質を分解、揮発させることによって除去し、導電性粒子を加熱融着させることにより、導電性被膜を形成する。イオン交換能を有する物質が共存することによって、保護物質の分解等が促進されるので、前記(i)の方法よりも効率的に導電性被膜を形成することができる。
(iii)被覆導電性粒子を対象に塗工し、形成された導電性被膜前駆体に、保護物質のイオン性に対応するイオン交換能を有する物質を含むイオン交換層と接触させる、あるいは、保護物質のイオンに対応するイオン交換能を対象に塗工し、形成されたイオン交換層と導電性被膜前駆体と接触させる。すると、イオン交換反応により、導電性粒子表面から保護物質が引き剥がされ、活性エネルギーの高い導電性粒子の表面が露出するので、導電性粒子の被膜化が速やかに進行し、導電性被膜をより低温(例えば200℃以下)、短時間で得ることが可能となる。
Next, a general method for forming a conductive film from a dispersion of coated conductive particles will be described.
The protective substance covers the surface of the conductive particles in the state of the dispersion, prevents aggregation of the conductive particles, and contributes to the dispersion stability as the dispersion. The conductive film can be obtained by peeling the protective substance from the conductive particles by the following method and heating and fusing the conductive particles.
(I) After coating the dispersion, the protective substance is removed by decomposition and volatilization by heating, and the conductive particles are heated and fused to form a conductive film.
(Ii) After coating a dispersion containing a substance having ion exchange ability corresponding to the ionicity of the protective substance in addition to the coated conductive particles, the protective substance is removed by decomposition and volatilization by heating; A conductive film is formed by heat-sealing the conductive particles. The coexistence of the substance having ion exchange ability promotes the decomposition of the protective substance, so that the conductive film can be formed more efficiently than the method (i).
(Iii) The coated conductive particles are applied to the target, and the formed conductive film precursor is brought into contact with or protected from an ion exchange layer containing a substance having ion exchange ability corresponding to the ionicity of the protective substance. The ion exchange capability corresponding to the ions of the substance is applied to the target, and the formed ion exchange layer is brought into contact with the conductive film precursor. Then, the protective material is peeled off from the surface of the conductive particles by the ion exchange reaction, and the surface of the conductive particles having a high active energy is exposed. It can be obtained at a low temperature (for example, 200 ° C. or less) in a short time.
本発明の電磁波シールド性接着性フィルムは、硬化性導電性接着剤層の他に、前記の被覆導電性粒子の分散体から形成される導電性被膜を具備するものであり、前記(i)イオン交換層を利用しない製造方法により形成することができる。 The electromagnetic wave shielding adhesive film of the present invention comprises, in addition to the curable conductive adhesive layer, a conductive film formed from a dispersion of the coated conductive particles, and the (i) ion It can be formed by a manufacturing method that does not use an exchange layer.
イオン交換層を利用しない製造方法としては、図1及び図2のような方法があり、
(1−1)硬化性を有しない絶縁フィルム(II)に、平均粒子径が0.001〜0.5μmの導電性粒子が保護物質によって被覆されてなる被覆導電性粒子を含む分散液を塗工し、加熱し、導電性被膜(III)を形成する工程、
(1−2)前記導電性被膜(III)上に、硬化性絶縁性樹脂と、平均粒子径が1〜50μmの金属粉とを含有する硬化性導電性接着剤を塗工し、乾燥し、硬化性導電性接着剤層(I)を形成する工程、
(1−3)前記硬化性導電性接着剤層(I)の他方の面と、剥離性フィルムとを重ね合わせる。
As a manufacturing method not using an ion exchange layer, there are methods as shown in FIGS.
(1-1) A dispersion liquid containing coated conductive particles in which conductive particles having an average particle diameter of 0.001 to 0.5 μm are coated with a protective substance is applied to an insulating film (II) having no curability. A process of heating and forming a conductive coating (III),
(1-2) On the conductive coating (III), a curable conductive adhesive containing a curable insulating resin and a metal powder having an average particle diameter of 1 to 50 μm is applied and dried. Forming a curable conductive adhesive layer (I);
(1-3) The other surface of the curable conductive adhesive layer (I) is overlapped with the peelable film.
あるいは
(2−1)硬化性を有しない絶縁フィルム(II)に、平均粒子径が0.001〜0.5μmの導電性粒子が保護物質によって被覆されてなる被覆導電性粒子を含む分散液を塗工し、加熱し、導電性被膜(III)を形成する工程、
(2−2)剥離性フィルムの一方の面に、硬化性絶縁性樹脂と、平均粒子径が1〜50μmの金属粉とを含有する硬化性導電性接着剤を塗工し、乾燥し、硬化性導電性接着剤層(I)を形成する工程、
(2−3)前記硬化性導電性接着剤層(I)と、前記導電性被膜(III)とを重ね合わせる。
Alternatively, (2-1) a dispersion containing coated conductive particles in which conductive particles having an average particle diameter of 0.001 to 0.5 μm are coated with a protective substance on an insulating film (II) having no curability. Applying and heating to form a conductive coating (III);
(2-2) One side of the peelable film is coated with a curable conductive adhesive containing a curable insulating resin and a metal powder having an average particle diameter of 1 to 50 μm, dried and cured. Forming the conductive conductive adhesive layer (I),
(2-3) The curable conductive adhesive layer (I) and the conductive coating (III) are overlapped.
上記の製造方法によって、本発明の硬化性を有しない絶縁フィルム、導電性被膜、及び硬化性導電性接着剤層をこの順序で具備する、電磁波シールド性接着性フィルムを得る事ができる。 By the above production method, an electromagnetic wave shielding adhesive film comprising the insulating film having no curability of the present invention, a conductive coating, and a curable conductive adhesive layer in this order can be obtained.
導電性粒子を含む分散体は、導電性インキとして、グラビア印刷、マイクログラビア印刷、フレキソ印刷、スクリーン印刷、インクジェット印刷、ディスペンサー印刷、スプレーコート、スピンコート、ダイコート、リップコート、ナイフコート、ディップコート、カーテンコート、ロールコート、バーコート等各種印刷方式へ適用することも可能であり、必要に応じて、導電性粒子を含む分散体の物性、安定性、印刷性、塗工性といった印刷インキとしての性能等を高める目的で、消泡剤、レベリング剤、滑剤、分散剤、樹脂および/またはその前駆体等を含ませることもできる。このときの加熱処理の温度は300℃以下であることが好ましく、フィルム基材上での導電性被膜形成を考慮すると200℃以下であることが好ましい。さらに160℃以下であることが好ましい。 Dispersion containing conductive particles, as conductive ink, gravure printing, micro gravure printing, flexographic printing, screen printing, inkjet printing, dispenser printing, spray coating, spin coating, die coating, lip coating, knife coating, dip coating, It can also be applied to various printing methods such as curtain coating, roll coating, and bar coating, and if necessary, as a printing ink such as physical properties, stability, printability, and coating properties of a dispersion containing conductive particles. For the purpose of enhancing performance and the like, an antifoaming agent, leveling agent, lubricant, dispersant, resin and / or precursor thereof may be included. The temperature of the heat treatment at this time is preferably 300 ° C. or lower, and preferably 200 ° C. or lower in consideration of formation of a conductive film on the film substrate. Furthermore, it is preferable that it is 160 degrees C or less.
乾燥の方法については、特に限定されず、例えば、熱風乾燥、遠赤外線乾燥、紫外線乾燥、電子エネルギー乾燥、熱ロール乾燥等、一般的な乾燥方法を用いることができる。
また、形成される導電性被膜(III)は、厚みが0.001〜20μmであることが好ましく、より好ましくは0.05〜10μmである。表面抵抗率は、前述したように1×10-2〜1×102(Ω/□)である事が好ましく、より好ましくは1×10−1〜1×101(Ω/□)である。
The drying method is not particularly limited, and general drying methods such as hot air drying, far-infrared drying, ultraviolet drying, electronic energy drying, and hot roll drying can be used.
Moreover, it is preferable that the thickness of the conductive film (III) to be formed is 0.001 to 20 μm, and more preferably 0.05 to 10 μm. As described above, the surface resistivity is preferably 1 × 10 −2 to 1 × 10 2 (Ω / □), more preferably 1 × 10 −1 to 1 × 10 1 (Ω / □). .
次に本発明にて使用する剥離性フィルムについて説明する。
剥離性フィルムは、片面あるいは両面に離型処理をしたフィルムや、片面あるいは両面に粘着剤を塗布したフィルムなどを使用することができる。
剥離性フィルムの基材としては、ポリエチレンテレフタレート、ポリエチレンナフタレート、ポリフッ化ビニル、ポリフッ化ビニリデン、硬質ポリ塩化ビニル、ポリ塩化ビニリデン、ナイロン、ポリイミド、ポリスチレン、ポリビニルアルコール、エチレン・ビニルアルコール共重合体、ポリカーボネート、ポリアクリロニトリル、ポリブテン、軟質ポリ塩化ビニル、ポリフッ化ビニリデン、ポリエチレン、ポリプロピレン、ポリウレタン、エチレン酢酸ビニル共重合体、ポリ酢酸ビニル等のプラスチックシート等、グラシン紙、上質紙、クラフト紙、コート紙等の紙類、各種の不織布、合成紙、金属箔や、これらを組み合わせた複合フィルムなどが挙げられる。
Next, the peelable film used in the present invention will be described.
As the peelable film, a film having a release treatment on one side or both sides, a film having an adhesive applied on one side or both sides, and the like can be used.
As the substrate of the peelable film, polyethylene terephthalate, polyethylene naphthalate, polyvinyl fluoride, polyvinylidene fluoride, rigid polyvinyl chloride, polyvinylidene chloride, nylon, polyimide, polystyrene, polyvinyl alcohol, ethylene / vinyl alcohol copolymer, Plastic sheets such as polycarbonate, polyacrylonitrile, polybutene, soft polyvinyl chloride, polyvinylidene fluoride, polyethylene, polypropylene, polyurethane, ethylene vinyl acetate copolymer, polyvinyl acetate, glassine paper, fine paper, kraft paper, coated paper, etc. Paper, various non-woven fabrics, synthetic paper, metal foil, and composite films combining these.
離型処理をしたフィルムは、離型剤を剥離性フィルムの基材の片面あるいは両面に塗布したり、物理的にマット化処理をして得る事ができる。
離型剤としては、ポリエチレン、ポリプロピレン等の炭化水素系樹脂、高級脂肪酸及びその金属塩、高級脂肪酸石鹸、ワックス、動植物油脂、マイカ、タルク、シリコーン系界面活性剤、シリコーンオイル、シリコーン樹脂、フッ素系界面活性剤、フッ素樹脂、フッ素含有シリコーン樹脂などが用いられる。
離型剤の塗布方法としては、従来公知の方式、例えば、グラビアコート方式、キスコート方式、ダイコート方式、リップコート方式、コンマコート方式、ブレードコート方式、ロールコート方式、ナイフコート方式、スプレーコート方式、バーコート方式、スピンコート方式、ディップコート方式等により行うことができる。
The film subjected to the mold release treatment can be obtained by applying a mold release agent to one or both sides of the substrate of the peelable film or by physically matting the film.
Release agents include hydrocarbon resins such as polyethylene and polypropylene, higher fatty acids and their metal salts, higher fatty acid soaps, waxes, animal and vegetable fats and oils, mica, talc, silicone surfactants, silicone oils, silicone resins, and fluorine-based agents. Surfactants, fluorine resins, fluorine-containing silicone resins, and the like are used.
As a method for applying the release agent, conventionally known methods such as gravure coating method, kiss coating method, die coating method, lip coating method, comma coating method, blade coating method, roll coating method, knife coating method, spray coating method, It can be performed by a bar coating method, a spin coating method, a dip coating method, or the like.
粘着剤を塗布したフィルムは、剥離性フィルムの基材の片面あるいは両面にアクリル系樹脂、シリコーン系樹脂またはゴム系樹脂と架橋剤とを含んでなる粘着剤を塗布して得ることができる。 The film coated with the pressure-sensitive adhesive can be obtained by applying a pressure-sensitive adhesive comprising an acrylic resin, a silicone-based resin or a rubber-based resin and a crosslinking agent to one or both sides of the base of the peelable film.
粘着剤の塗布方法としては、従来公知の方式、例えば、グラビアコート方式、キスコート方式、ダイコート方式、リップコート方式、コンマコート方式、ブレードコート方式、ロールコート方式、ナイフコート方式、スプレーコート方式、バーコート方式、スピンコート方式、ディップコート方式等により行うことができる。 As a method for applying the adhesive, conventionally known methods such as gravure coating method, kiss coating method, die coating method, lip coating method, comma coating method, blade coating method, roll coating method, knife coating method, spray coating method, bar A coating method, a spin coating method, a dip coating method, or the like can be used.
最後に本発明の電磁波シールド性接着性フィルムの使い方の具体的態様を説明する。
前記電磁波シールド性接着性フィルムから、一部の態様を除き、剥離性フィルムを剥がし、硬化性導電性接着剤層(I)を露出させる。その硬化性導電性接着剤層(I)を被着体に重ね合わせ、加熱することにより、硬化性導電性接着剤層(I)を硬化させ、硬化に伴い、導電性被膜(III)と硬化性導電性接着剤層(I)との接着が確保され、被着体を電磁波から遮蔽することが可能となる。
本発明の硬化性電磁波シールド性接着性フィルムを貼着することのできる被着体としては、例えば、繰り返し屈曲を受けるフレキシブルプリント配線板を代表例として挙げることができる。もちろん、リジッドプリント配線板にも適用できる。
Finally, a specific embodiment of how to use the electromagnetic wave shielding adhesive film of the present invention will be described.
Except for some aspects, the peelable film is peeled off from the electromagnetic wave shielding adhesive film to expose the curable conductive adhesive layer (I). The curable conductive adhesive layer (I) is superimposed on the adherend and heated to cure the curable conductive adhesive layer (I), and with the curing, the conductive film (III) is cured. Adhesion with the conductive conductive adhesive layer (I) is ensured, and the adherend can be shielded from electromagnetic waves.
As a to-be-adhered body which can stick the curable electromagnetic wave shielding adhesive film of this invention, the flexible printed wiring board which receives a bending repeatedly can be mentioned as a representative example, for example. Of course, it can also be applied to rigid printed wiring boards.
次に、実施例を示して本発明を更に詳細に説明するが、本発明はこれらによって限定されるものではない。実施例及び比較例において、「部」及び「%」とあるのは、「重量部」及び「重量%」をそれぞれ意味するものとする。
なお、実施例中に記載したポリウレタンポリウレア樹脂の重量平均分子量、及びポリエステル樹脂の数平均分子量は、GPC測定で求めたポリスチレン換算の重量平均分子量、及び数平均分子量であり、GPC測定の条件は、以下のとおりである。
装置:Shodex GPC System−21(昭和電工製)
カラム:Shodex KF−802、KF−803L、KF−805L
(昭和電工製)の合計3本を連結して使用。
溶媒:テトラヒドロフラン
流速:1.0ml/min
温度:40℃
試料濃度:0.3重量%
試料注入量:100μl
Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited thereto. In Examples and Comparative Examples, “parts” and “%” mean “parts by weight” and “% by weight”, respectively.
In addition, the weight average molecular weight of the polyurethane polyurea resin described in the Examples, and the number average molecular weight of the polyester resin are the weight average molecular weight in terms of polystyrene and the number average molecular weight determined by GPC measurement, and the conditions for the GPC measurement are as follows: It is as follows.
Equipment: Shodex GPC System-21 (manufactured by Showa Denko)
Column: Shodex KF-802, KF-803L, KF-805L
A total of 3 (made by Showa Denko) are connected and used.
Solvent: Tetrahydrofuran Flow rate: 1.0 ml / min
Temperature: 40 ° C
Sample concentration: 0.3% by weight
Sample injection volume: 100 μl
[ポリウレタンポリウレア樹脂(A)の合成]
[合成例1]
攪拌機、温度計、還流冷却器、滴下装置、窒素導入管を備えた反応容器に、アジピン酸とテレフタル酸及び3−メチル−1,5−ペンタンジオールから得られる数平均分子量(以下、「Mn」という)=1006であるジオール414部、ジメチロールブタン酸8部、イソホロンジイソシアネート145部、及びトルエン40部を仕込み、窒素雰囲気下90℃で3時間反応させた。これに、トルエン300部を加えて、末端にイソシアネート基を有するウレタンプレポリマーの溶液を得た。次に、イソホロンジアミン27部、ジ−n−ブチルアミン3部、2−プロパノール342部、及びトルエン576部を混合したものに、得られたウレタンプレポリマーの溶液816部を添加し、70℃で3時間反応させ、重量平均分子量(以下、「Mw」という)=54,000、酸価5mgKOH/gであるポリウレタンポリウレア樹脂の溶液を得た。これに、トルエン144部、2−プロパノール72部を加えて、固形分30%であるポリウレタンポリウレア樹脂溶液(A−1))を得た。
[Synthesis of polyurethane polyurea resin (A)]
[Synthesis Example 1]
A number average molecular weight (hereinafter referred to as “Mn”) obtained from adipic acid, terephthalic acid and 3-methyl-1,5-pentanediol in a reaction vessel equipped with a stirrer, a thermometer, a reflux condenser, a dropping device, and a nitrogen introduction tube. Diol = 414, dimethylol butanoic acid 8 parts, isophorone diisocyanate 145 parts and toluene 40 parts were charged and reacted at 90 ° C. for 3 hours in a nitrogen atmosphere. To this, 300 parts of toluene was added to obtain a urethane prepolymer solution having an isocyanate group at the terminal. Next, 816 parts of the obtained urethane prepolymer solution was added to a mixture of 27 parts of isophoronediamine, 3 parts of di-n-butylamine, 342 parts of 2-propanol, and 576 parts of toluene. By reacting for a time, a polyurethane polyurea resin solution having a weight average molecular weight (hereinafter referred to as “Mw”) = 54,000 and an acid value of 5 mgKOH / g was obtained. To this, 144 parts of toluene and 72 parts of 2-propanol were added to obtain a polyurethane polyurea resin solution (A-1) having a solid content of 30%.
[合成例2]
攪拌機、温度計、還流冷却器、滴下装置、窒素導入管を備えた反応容器に、アジピン酸と3−メチル−1,5−ペンタンジオール及び1,6−ヘキサンカーボネートジオールとから得られるMn=981であるジオール390部、ジメチロールブタン酸16部、イソホロンジイソシアネート158部、及びトルエン40部を仕込み、窒素雰囲気下90℃で3時間反応させた。これに、トルエン300部を加えて、末端にイソシアネート基を有するウレタンプレポリマーの溶液を得た。次に、イソホロンジアミン29部、ジ−n−ブチルアミン3部、2−プロパノール342部、及びトルエン576部を混合したものに、得られたウレタンプレポリマーの溶液814部を添加し、70℃で3時間反応させ、Mw=43,000、酸価10mgKOH/gであるポリウレタンポリウレア樹脂の溶液を得た。これに、トルエン144部、2−プロパノール72部を加えて、固形分30%であるポリウレタンポリウレア樹脂溶液(A−2))を得た。
[Synthesis Example 2]
Mn = 981 obtained from adipic acid, 3-methyl-1,5-pentanediol and 1,6-hexane carbonate diol in a reaction vessel equipped with a stirrer, thermometer, reflux condenser, dropping device, and nitrogen introduction tube Diol 390, dimethylolbutanoic acid 16 parts, isophorone diisocyanate 158 parts, and toluene 40 parts were charged and reacted at 90 ° C. for 3 hours in a nitrogen atmosphere. To this, 300 parts of toluene was added to obtain a urethane prepolymer solution having an isocyanate group at the terminal. Next, 814 parts of the resulting urethane prepolymer solution was added to a mixture of 29 parts of isophorone diamine, 3 parts of di-n-butylamine, 342 parts of 2-propanol, and 576 parts of toluene. By reacting for a period of time, a polyurethane polyurea resin solution having Mw = 43,000 and an acid value of 10 mgKOH / g was obtained. To this, 144 parts of toluene and 72 parts of 2-propanol were added to obtain a polyurethane polyurea resin solution (A-2) having a solid content of 30%.
[合成例3]
攪拌機、温度計、還流冷却器、滴下装置、窒素導入管を備えた反応容器に、アジピン酸と3−メチル−1,5−ペンタンジオールとから得られるMn=1002であるジオール352部、ジメチロールブタン酸32部、イソホロンジイソシアネート176部、及びトルエン40部を仕込み、窒素雰囲気下90℃で3時間反応させた。これに、トルエン300部を加えて、末端にイソシアネート基を有するウレタンプレポリマーの溶液を得た。次に、イソホロンジアミン32部、ジ−n−ブチルアミン4部、2−プロパノール342部、及びトルエン576部を混合したものに、得られたウレタンプレポリマーの溶液810部を添加し、70℃で3時間反応させ、Mw=35,000、酸価21mgKOH/gであるポリウレタンポリウレア樹脂の溶液を得た。これに、トルエン144部、2−プロパノール72部を加えて、固形分30%であるポリウレタンポリウレア樹脂溶液(A−3))を得た。
[Synthesis Example 3]
A reaction vessel equipped with a stirrer, a thermometer, a reflux condenser, a dropping device, and a nitrogen introduction tube, 352 parts of diol having Mn = 1002 obtained from adipic acid and 3-methyl-1,5-pentanediol, dimethylol 32 parts of butanoic acid, 176 parts of isophorone diisocyanate and 40 parts of toluene were charged and reacted at 90 ° C. for 3 hours in a nitrogen atmosphere. To this, 300 parts of toluene was added to obtain a urethane prepolymer solution having an isocyanate group at the terminal. Next, 810 parts of the obtained urethane prepolymer solution was added to a mixture of 32 parts of isophoronediamine, 4 parts of di-n-butylamine, 342 parts of 2-propanol, and 576 parts of toluene, By reacting for a period of time, a polyurethane polyurea resin solution having Mw = 35,000 and an acid value of 21 mgKOH / g was obtained. To this, 144 parts of toluene and 72 parts of 2-propanol were added to obtain a polyurethane polyurea resin solution (A-3) having a solid content of 30%.
[被覆導電性粒子の分散体 合成例1]
セパラブル4口フラスコに冷却管、温度計、窒素ガス導入管、撹拌装置を取り付け、窒素雰囲気下、室温で撹拌しながらトルエン200部およびオレイン酸銀38.9部を仕込み、0.5Mの溶液とした後に、分散剤としてジエチルアミノエタノール2.3部(金属1molに対し0.2mol倍)を添加し溶解させた。
その後、還元剤として20%コハク酸ジヒドラジド(以降SUDHと略記する)水溶液73.1部(金属1molに対しヒドラジド基2mol倍)を滴下すると液色が淡黄色から濃茶色に変化した。更に反応を促進させるために40℃に昇温し、反応を進行させた。静置、分離した後、水層を取り出すことで過剰の還元剤や不純物を除去し、更にトルエン層に数回蒸留水を加え、洗浄・分離を繰り返し、オレイン酸で保護された銀微粒子がトルエンに分散してなる分散体を得た。得られた銀微粒子分散体の、銀微粒子の平均粒子径は7±2nmであり、銀濃度は73%であり、40℃で一ヶ月保存した後でも粒子径に変化はなく安定であった。
[Dispersion of coated conductive particles Synthesis Example 1]
Attach 200 parts of toluene and 38.9 parts of silver oleate to a separable four-necked flask with a condenser, thermometer, nitrogen gas inlet tube, and stirring device, and stir at room temperature in a nitrogen atmosphere. After that, 2.3 parts of diethylaminoethanol (0.2 mol times with respect to 1 mol of metal) was added and dissolved as a dispersant.
Thereafter, when 73.1 parts of 20% aqueous succinic acid dihydrazide (hereinafter abbreviated as SUDH) as a reducing agent (2 mol times of hydrazide group with respect to 1 mol of metal) was dropped, the liquid color changed from light yellow to dark brown. In order to further promote the reaction, the temperature was raised to 40 ° C. to advance the reaction. After standing and separating, the aqueous layer is taken out to remove excess reducing agent and impurities. Further, distilled water is added several times to the toluene layer, washing and separation are repeated, and silver fine particles protected with oleic acid are added to toluene. To obtain a dispersion. In the obtained silver fine particle dispersion, the average particle diameter of silver fine particles was 7 ± 2 nm, the silver concentration was 73%, and the particle diameter did not change even after being stored at 40 ° C. for one month and was stable.
[被覆導電性粒子の分散体 合成例2]
セパラブル4口フラスコに冷却管、温度計、窒素ガス導入管、撹拌装置を取り付け、窒素雰囲気下、室温で撹拌しながらトルエン200部およびプロピオン酸銀18.1部を仕込み、0.5Mの溶液とした後に、分散剤としてジエチルアミノエタノール2.3部(金属1molに対し0.2mol倍)、オレイン酸2.8部(金属1molに対し0.1mol倍)を添加し溶解させた。
その後、還元剤として20%SUDH水溶液73.1部(金属1molに対しヒドラジド基2mol倍)を添加すると液色が淡黄色から濃茶色に変化した。更に反応を促進させるために40℃に昇温し、反応を進行させた。静置、分離した後、水層を取り出すことで過剰の還元剤や不純物を除去し、更にトルエン層に数回蒸留水を加え、洗浄・分離を繰り返し、プロピオン酸及びオレイン酸で保護された銀微粒子がトルエンに分散してなる分散体を得た。得られた銀微粒子分散体の、銀微粒子の平均粒子径は5±2nmであり、銀濃度は75%であり、40℃で一ヶ月保存した後でも粒子径に変化はなく安定であった。
[Dispersion of coated conductive particles Synthesis Example 2]
Attach 200 parts of toluene and 18.1 parts of silver propionate to a separable four-necked flask equipped with a cooling tube, thermometer, nitrogen gas introduction tube and stirring device while stirring at room temperature in a nitrogen atmosphere. Then, 2.3 parts of diethylaminoethanol (0.2 mol times with respect to 1 mol of metal) and 2.8 parts of oleic acid (0.1 mol times with respect to 1 mol of metal) were added and dissolved as a dispersant.
Thereafter, when 73.1 parts of 20% SUDH aqueous solution (2 mol times of hydrazide group with respect to 1 mol of metal) was added as a reducing agent, the liquid color changed from light yellow to dark brown. In order to further promote the reaction, the temperature was raised to 40 ° C. to advance the reaction. After standing and separating, the aqueous layer is taken out to remove excess reducing agent and impurities, and distilled water is added to the toluene layer several times, washing and separation are repeated, and silver protected with propionic acid and oleic acid A dispersion formed by dispersing fine particles in toluene was obtained. The obtained silver fine particle dispersion had an average particle diameter of 5 ± 2 nm, a silver concentration of 75%, and was stable with no change in particle diameter even after being stored at 40 ° C. for one month.
[被覆導電性粒子の分散体 合成例 3]
原料の金属塩をペンタン酸銀20.9部に変更した以外は、合成例2と同様にしてペンタン酸及びオレイン酸で保護された銀微粒子分散体を得た。得られた銀微粒子分散体の、銀微粒子の平均粒子径は5±1nmであり、銀濃度は82%であり、40℃で一ヶ月保存した後でも粒子径に変化はなく安定であった。
[Dispersion of coated conductive particles, Synthesis Example 3]
A silver fine particle dispersion protected with pentanoic acid and oleic acid was obtained in the same manner as in Synthesis Example 2 except that the starting metal salt was changed to 20.9 parts of silver pentanoate. The obtained silver fine particle dispersion had an average particle diameter of 5 ± 1 nm, a silver concentration of 82%, and was stable with no change in particle diameter even after being stored at 40 ° C. for one month.
[被覆導電性粒子の分散体 合成例 4]
原料の金属塩をヘキサン酸銀22.3部に変更した以外は、合成例2と同様にしてヘキサン酸及びオレイン酸で保護された銀微粒子分散体を得た。得られた銀微粒子分散体の、銀微粒子の平均粒子径は5±2nmであり、銀濃度は80%であり、40℃で一ヶ月保存した後でも粒子径に変化はなく安定であった。
[Dispersion of coated conductive particles, Synthesis Example 4]
A silver fine particle dispersion protected with hexanoic acid and oleic acid was obtained in the same manner as in Synthesis Example 2, except that the starting metal salt was changed to 22.3 parts of silver hexanoate. The obtained silver fine particle dispersion had an average particle size of 5 ± 2 nm, a silver concentration of 80%, and was stable with no change in particle size even after storage at 40 ° C. for one month.
[被覆導電性粒子の分散体 合成例 5]
原料の金属塩をオクタン酸銀25.1部に変更した以外は、合成例2と同様にしてオクタン酸及びオレイン酸で保護された銀微粒子分散体を得た。得られた銀微粒子分散体の銀微粒子の平均粒子径は6±2nmであり、銀濃度は70%であり、40℃で一ヶ月保存した後でも粒子径に変化はなく安定であった。
[Dispersion of coated conductive particles, Synthesis Example 5]
A silver fine particle dispersion protected with octanoic acid and oleic acid was obtained in the same manner as in Synthesis Example 2 except that the starting metal salt was changed to 25.1 parts of silver octoate. The average particle diameter of the silver fine particles of the obtained silver fine particle dispersion was 6 ± 2 nm, the silver concentration was 70%, and the particle diameter did not change and was stable even after storage at 40 ° C. for one month.
[被覆導電性粒子の分散体 合成例 6]
原料の金属塩をミリスチン酸銀33.5部に変更した以外は、合成例2と同様にしてミリスチン酸及びオレイン酸で保護された銀微粒子分散体を得た。得られた銀微粒子分散体の銀微粒子の平均粒子径は8±2nmであり、銀濃度は72%であり、40℃で一ヶ月保存した後でも粒子径に変化はなく安定であった。
[Dispersion of coated conductive particles, Synthesis Example 6]
A silver fine particle dispersion protected with myristic acid and oleic acid was obtained in the same manner as in Synthesis Example 2 except that the raw metal salt was changed to 33.5 parts of silver myristic acid. The average particle diameter of the silver fine particles of the obtained silver fine particle dispersion was 8 ± 2 nm, the silver concentration was 72%, and the particle diameter did not change even after storage at 40 ° C. for one month and was stable.
[被覆導電性粒子の分散体 合成例 7]
原料の金属塩をステアリン酸銀39.1部に変更した以外は、合成例2と同様にしてステアリン酸及びオレイン酸で保護された銀微粒子分散体を得た。得られた銀微粒子分散体の銀微粒子の平均粒子径は8±2nmであり、銀濃度は65% であり、40℃で一ヶ月保存した後でも粒子径に変化はなく安定であった。
[Dispersion of coated conductive particles, Synthesis Example 7]
A silver fine particle dispersion protected with stearic acid and oleic acid was obtained in the same manner as in Synthesis Example 2 except that the starting metal salt was changed to 39.1 parts of silver stearate. The average particle size of the silver fine particles of the obtained silver fine particle dispersion was 8 ± 2 nm, the silver concentration was 65%, and the particle size did not change even after being stored at 40 ° C. for one month and was stable.
[被覆導電性粒子の分散体 合成例8]
原料の金属塩をブタン酸銀19.5部に変更した以外は合成例2と同様にしてブタン酸及びオレイン酸で保護された銀微粒子分散体を得た。得られた銀微粒子分散体の銀微粒子の平均粒子径は5±2nmであり、銀濃度は75%であり、40℃で一ヶ月保存した後でも粒子径に変化はなく安定であった。
[Dispersion of coated conductive particles, Synthesis Example 8]
A silver fine particle dispersion protected with butanoic acid and oleic acid was obtained in the same manner as in Synthesis Example 2 except that the starting metal salt was changed to 19.5 parts of silver butanoate. The average particle diameter of the silver fine particles of the obtained silver fine particle dispersion was 5 ± 2 nm, the silver concentration was 75%, and the particle diameter did not change even after being stored at 40 ° C. for one month and was stable.
[被覆導電性粒子の分散体 合成例 9]
原料の金属塩をペンタン酸銅16.5部に、還元剤を20%SUDH水溶液146.2部(金属1molに対しヒドラジド基4molの割合)に変更した以外は合成例2と同様にしてペンタン酸及びオレイン酸で保護された銅微粒子分散体を得た。得られた銅微粒子分散体の銅粒子の平均粒子径は、7±2nmであり、銅濃度は75%であり、40℃で一ヶ月保存した後でも粒子径に変化はなく安定であった。
[Dispersion of coated conductive particles, Synthesis Example 9]
Similar to Synthesis Example 2, except that the starting metal salt is changed to 16.5 parts of copper pentanoate and the reducing agent is changed to 146.2 parts of 20% SUDH aqueous solution (ratio of 4 mol of hydrazide group to 1 mol of metal). And the copper fine particle dispersion protected with oleic acid was obtained. The average particle size of the copper particles of the obtained copper fine particle dispersion was 7 ± 2 nm, the copper concentration was 75%, and the particle size did not change even after being stored at 40 ° C. for one month and was stable.
[被覆導電性粒子の分散体 合成例 10]
セパラブル4口フラスコに冷却管、温度計、窒素ガス導入管、撹拌装置を取り付け、窒素雰囲気下、室温で撹拌しながらトルエン200部およびプロピオン酸銀18.1部を仕込み、0.5Mの溶液とした後に、分散剤としてジエチルアミノエタノール2.3部(金属1molに対し0.2mol倍)、アジスパーPB821(味の素ファインテクノ株式会社製)1.1部(金属に対し10重量%)を20%トルエン溶液として添加し溶解させた。
その後、還元剤として20%SUDH水溶液73.1部(金属1molに対しヒドラジド基2mol倍)を添加すると液色が淡黄色から濃茶色に変化した。更に反応を促進させるために4 0℃ に昇温し、反応を進行させた。静置、分離した後、水層を取り出すことで過剰の還元剤や不純物を除去し、更にトルエン層に数回蒸留水を加え、洗浄・分離を繰り返し、プロピオン酸及びアジスパーPB821で保護された銀微粒子がトルエンに分散してなる分散体を得た。得られた銀微粒子分散体の、銀微粒子の平均粒子径は5±2nmであり、銀濃度は68%であり、40℃で一ヶ月保存した後でも粒子径に変化はなく安定であった。
[Dispersion of coated conductive particles, Synthesis Example 10]
Attach 200 parts of toluene and 18.1 parts of silver propionate to a separable four-necked flask equipped with a cooling tube, thermometer, nitrogen gas introduction tube and stirring device while stirring at room temperature in a nitrogen atmosphere. Then, 2.3 parts of diethylaminoethanol (0.2 mol times with respect to 1 mol of metal) and 1.1 parts of Ajisper PB821 (manufactured by Ajinomoto Fine-Techno Co., Ltd.) (10% by weight with respect to the metal) as a dispersant Added and dissolved.
Thereafter, when 73.1 parts of 20% SUDH aqueous solution (2 mol times of hydrazide group with respect to 1 mol of metal) was added as a reducing agent, the liquid color changed from light yellow to dark brown. In order to further promote the reaction, the temperature was raised to 40 ° C. to advance the reaction. After standing and separation, the aqueous layer is taken out to remove excess reducing agent and impurities, and distilled water is added to the toluene layer several times, washing and separation are repeated, and silver protected with propionic acid and Ajisper PB821 A dispersion formed by dispersing fine particles in toluene was obtained. The obtained silver fine particle dispersion had an average particle size of 5 ± 2 nm, a silver concentration of 68%, and was stable with no change in particle size even after being stored at 40 ° C. for one month.
[被覆導電性粒子の分散体 合成例11]
セパラブル4口フラスコに冷却管、温度計、窒素ガス導入管、攪拌装置を取り付け、窒素ガスを導入しながら1M硝酸銀水溶液を100部仕込み、攪拌しながらソルスパース32000(日本ルーブリゾール株式会社製、重量平均分子量約50000)1.9部を、トルエン10.8 部中に溶解させた溶液を滴下した。室温で30分攪拌した後、ジメチルアミノエタノール38.1部を滴下し、そのまま室温で一晩攪拌し反応を進行させた。水層を取り出し、数回蒸留水で洗浄・分離を繰返すことで過剰の還元剤と不純物の洗浄を行い、ソルスパース32000で保護された銀微粒子がトルエンに分散してなる分散体を得た。得られた銀微粒子分散体は、ペースト状であり、銀微粒子の平均粒子径は25±10nmであり、銀濃度は50%であった。
[Dispersion of coated conductive particles Synthesis Example 11]
A separable four-necked flask was equipped with a condenser, thermometer, nitrogen gas inlet tube, and stirring device. While introducing nitrogen gas, 100 parts of 1M silver nitrate aqueous solution was charged, and while stirring, Solsperse 32000 (Nippon Lubrizol Corporation, weight average) A solution prepared by dissolving 1.9 parts of a molecular weight of about 50000) in 10.8 parts of toluene was added dropwise. After stirring at room temperature for 30 minutes, 38.1 parts of dimethylaminoethanol was added dropwise, and the reaction was allowed to proceed overnight by stirring at room temperature. The aqueous layer was taken out, washed repeatedly with distilled water several times, and excessive reducing agent and impurities were washed to obtain a dispersion in which silver fine particles protected with Solsperse 32000 were dispersed in toluene. The obtained silver fine particle dispersion was in the form of a paste, the average particle size of the silver fine particles was 25 ± 10 nm, and the silver concentration was 50%.
[実施例1]
<工程(1−1)>
厚み12.5μmポリイミドフィルムの片面に、[被覆導電性微粒子の分散体 合成例1]で得られた分散体を塗工し、180℃×10分乾燥させて、導電性被膜(III)を具備するフィルム(1)を作製した。
[Example 1]
<Step (1-1)>
A dispersion obtained in [Dispersion of coated conductive fine particles Synthesis Example 1] is applied to one side of a polyimide film having a thickness of 12.5 μm, and dried at 180 ° C. for 10 minutes to provide a conductive coating (III). A film (1) to be produced was prepared.
<工程(1−2)>
別途、ポリウレタンポリウレア樹脂溶液(A−1)333部に対して、エポキシ樹脂(B−1)20部を加えて接着樹脂組成物を得た。この接着樹脂組成物353部に対して、導電フィラー(平均粒子径7μmの銀粉、福田金属箔粉工業製:AgXF301)120部を加えて攪拌混合し、ポリウレタンポリウレア樹脂(A−1)とエポキシ樹脂(B−1)との合計100重量部に対して、導電フィラー100部を含有する、硬化性導電性接着剤を得た。
得られた導電性接着剤を、フィルム(1)の導電性微粒子面に塗工し、100℃×2分乾燥させて、単位体積当たりの金属粉の含有量が1.2(g/cm3)、膜厚約7μmの硬化性導電性接着剤層(I)を具備するフィルム(2)を作製した。なお、硬化性導電性接着剤層(I)の表面抵抗率を後述する方法で求めたところ、0.2(Ω/□)であった。
<Process (1-2)>
Separately, 20 parts of epoxy resin (B-1) was added to 333 parts of polyurethane polyurea resin solution (A-1) to obtain an adhesive resin composition. 120 parts of a conductive filler (silver powder with an average particle diameter of 7 μm, manufactured by Fukuda Metal Foil Powder Industry: AgXF301) is added to 353 parts of the adhesive resin composition, and the mixture is stirred and mixed. The polyurethane polyurea resin (A-1) and the epoxy resin are mixed. A curable conductive adhesive containing 100 parts of a conductive filler was obtained with respect to 100 parts by weight in total with (B-1).
The obtained conductive adhesive is applied to the conductive fine particle surface of the film (1) and dried at 100 ° C. for 2 minutes, so that the content of metal powder per unit volume is 1.2 (g / cm 3). ), A film (2) comprising a curable conductive adhesive layer (I) having a thickness of about 7 μm was produced. In addition, when the surface resistivity of the curable conductive adhesive layer (I) was determined by the method described later, it was 0.2 (Ω / □).
<工程(1−3)>
続いて、厚み50μmポリエチレンテレフタレートフィルムの片面に微粘着剤20μmを設けた片面微粘着フィルムの微粘着剤面と、フィルム(2)の硬化性導電性接着剤層(I)面とをラミネーター(80℃、圧力2MPa、ラインスピード 2m/分)により貼り合せて、電磁波シールド性接着性フィルムを得た。
<Process (1-3)>
Subsequently, a laminator (80) was formed by attaching the fine adhesive surface of the single-sided microadhesive film in which the fine adhesive 20 μm was provided on one side of the 50 μm-thick polyethylene terephthalate film and the curable conductive adhesive layer (I) side of the film (2). Bonding was performed at 0 ° C., a pressure of 2 MPa, and a line speed of 2 m / min) to obtain an electromagnetic wave shielding adhesive film.
[実施例2]
<工程(2−1)>
厚み12.5μmポリイミドフィルムの片面に、[被覆導電性微粒子の分散体 合成例2]で得られた分散体を塗工し、100℃×15分乾燥させて、導電性被膜(III)を具備するフィルム(1)を作製した。
[Example 2]
<Process (2-1)>
The dispersion obtained in [Dispersion of coated conductive fine particles Synthesis Example 2] was applied to one side of a 12.5 μm-thick polyimide film and dried at 100 ° C. for 15 minutes to provide a conductive coating (III). A film (1) to be produced was prepared.
<工程(2−2)>
別途、ポリウレタンポリウレア樹脂溶液(A−2)333部に対して、エポキシ樹脂(B−1)20部を加えて接着樹脂組成物を得た。この接着樹脂組成物353部に対して、導電フィラー(平均粒子径5μmの銀粉、福田金属箔粉工業製:AgC222)120部を加えて攪拌混合し、ポリウレタンポリウレア樹脂(A−2)とエポキシ樹脂(B−1)との合計100重量部に対して、導電フィラー100部を含有する、硬化性導電性接着剤を得た。
<Step (2-2)>
Separately, 20 parts of epoxy resin (B-1) was added to 333 parts of polyurethane polyurea resin solution (A-2) to obtain an adhesive resin composition. 120 parts of a conductive filler (silver powder with an average particle diameter of 5 μm, manufactured by Fukuda Metal Foil Powder Industry Co., Ltd .: AgC222) is added to 353 parts of this adhesive resin composition, and the mixture is stirred and mixed. Polyurethane polyurea resin (A-2) and epoxy resin A curable conductive adhesive containing 100 parts of a conductive filler was obtained with respect to 100 parts by weight in total with (B-1).
<工程(2−3)>
得られた導電性接着剤を、片面に剥離処理を施した75μmのPETフィルムの剥離処理面に、単位体積当たりの金属粉の含有量が1.6(g/cm3)になるように塗工・乾燥しフィルム(2)を作製し、フィルム(2)の導電性接着剤面とフィルム(1)の導電性被膜面とをラミネーターにより貼り合せて電磁波シールド性接着性フィルムを得た。
<Process (2-3)>
The obtained conductive adhesive was applied to the peel-treated surface of a 75 μm PET film that had been peeled on one side so that the metal powder content per unit volume was 1.6 (g / cm 3 ). The film (2) was prepared by coating and drying, and the conductive adhesive surface of the film (2) and the conductive coating surface of the film (1) were bonded together by a laminator to obtain an electromagnetic wave shielding adhesive film.
[実施例3]
ポリウレタンポリウレア樹脂溶液、導電性微粒子種及びに導電性フィラー種を表1の通りに変更した以外は実施例1と同様の方法で電磁波シールド性接着性フィルムを得た。
[Example 3]
An electromagnetic wave shielding adhesive film was obtained in the same manner as in Example 1 except that the polyurethane polyurea resin solution, the conductive fine particle species and the conductive filler species were changed as shown in Table 1.
[実施例4]
エポキシ樹脂、導電性微粒子種及びに導電性フィラー種を表1の通りに変更した以外は実施例2と同様の方法で電磁波シールド性接着性フィルムを得た。
[Example 4]
An electromagnetic wave shielding adhesive film was obtained in the same manner as in Example 2 except that the epoxy resin, conductive fine particle species and conductive filler species were changed as shown in Table 1.
[実施例5]
絶縁層、エポキシ樹脂、導電性微粒子種及びに導電性フィラー配合量を表1の通りに変更した以外は実施例1と同様の方法で電磁波シールド性接着性フィルムを得た。
[Example 5]
An electromagnetic wave shielding adhesive film was obtained in the same manner as in Example 1 except that the insulating layer, the epoxy resin, the conductive fine particle species, and the conductive filler content were changed as shown in Table 1.
[実施例6]
絶縁層、導電性微粒子種、導電性フィラー種及びに配合量を表1の通りに変更した以外は実施例2と同様の方法で電磁波シールド性接着性フィルムを得た。
[Example 6]
An electromagnetic wave shielding adhesive film was obtained in the same manner as in Example 2, except that the insulating layer, the conductive fine particle type, the conductive filler type and the blending amount were changed as shown in Table 1.
[実施例7]
ポリウレタンポリウレア樹脂溶液、導電性微粒子種及びに導電性フィラー配合量を表1の通りに変更した以外は実施例1と同様の方法で電磁波シールド性接着性フィルムを得た。
[Example 7]
An electromagnetic wave shielding adhesive film was obtained in the same manner as in Example 1 except that the polyurethane polyurea resin solution, the conductive fine particle species, and the conductive filler content were changed as shown in Table 1.
[実施例8]
ポリウレタンポリウレア樹脂溶液、導電性フィラー種及びに配合量を表1の通りに変更した以外は実施例2と同様の方法で電磁波シールド性接着性フィルムを得た。
[Example 8]
An electromagnetic wave shielding adhesive film was obtained in the same manner as in Example 2 except that the polyurethane polyurea resin solution, the conductive filler species, and the blending amount were changed as shown in Table 1.
[実施例9]
エポキシ樹脂、導電性微粒子種及びに導電性フィラー配合量を表1の通りに変更した以外は実施例1と同様の方法で電磁波シールド性接着性フィルムを得た。
[Example 9]
An electromagnetic wave shielding adhesive film was obtained in the same manner as in Example 1 except that the epoxy resin, the conductive fine particle species, and the conductive filler content were changed as shown in Table 1.
[実施例10]
エポキシ樹脂、導電性微粒子種、導電性フィラー配合量を表1の通りに変更した以外は実施例2と同様の方法で電磁波シールド性接着性フィルムを得た。
[Example 10]
An electromagnetic wave shielding adhesive film was obtained in the same manner as in Example 2 except that the epoxy resin, conductive fine particle species, and conductive filler content were changed as shown in Table 1.
[実施例11]
絶縁層、導電性微粒子種及びに導電性フィラー配合量を表1の通りに変更した以外は実施例1と同様の方法で電磁波シールド性接着性フィルムを得た。
[Example 11]
An electromagnetic wave shielding adhesive film was obtained in the same manner as in Example 1 except that the insulating layer, the conductive fine particle species, and the conductive filler content were changed as shown in Table 1.
[実施例12]
絶縁層、導電性微粒子種、導電性フィラー種及びに配合量を表1の通りに変更した以外は実施例2と同様の方法で電磁波シールド性接着性フィルムを得た。
[Example 12]
An electromagnetic wave shielding adhesive film was obtained in the same manner as in Example 2, except that the insulating layer, the conductive fine particle type, the conductive filler type and the blending amount were changed as shown in Table 1.
[比較例1]
片面に剥離処理を施した50μmPETフィルムの剥離処理面に、ポリウレタンポリウレア樹脂溶液(C−1)333部に対して、エポキシ樹脂(D−1)20部を加えた絶縁性樹脂を塗工し、100℃×2分乾燥させて、硬化性絶縁層を具備するフィルム(1)を作製した。
[Comparative Example 1]
An insulating resin obtained by adding 20 parts of an epoxy resin (D-1) to 333 parts of a polyurethane polyurea resin solution (C-1) is applied to the release-treated surface of a 50 μm PET film subjected to a release process on one side, It was dried at 100 ° C. for 2 minutes to produce a film (1) having a curable insulating layer.
別途、ポリウレタンポリウレア樹脂溶液(A−1)333部に対して、エポキシ樹脂(B−1)20部を加えて接着樹脂組成物を得た。この接着樹脂組成物353部に対して、導電フィラー(福田金属箔粉工業製:AgXF301)120部を加えて攪拌混合し、ポリウレタンポリウレア樹脂(A−1)とエポキシ樹脂(B−1)との合計100重量部に対して、導電フィラー100部を含有する、硬化性導電性接着剤を得た。
得られた導電性接着剤を、片面に剥離処理を施した75μmのPETフィルムの剥離処理面に、塗工し、100℃×2分乾燥させて、単位体積当たりの金属粉の含有量が1.2(g/cm3)の硬化性導電性接着剤層を具備するフィルム(2)を作製した。硬化性導電性接着剤層の膜厚は約7μm、表面抵抗率は0.2(Ω/□)であった。
得られたフィルム(2)の硬化性導電性接着剤層面とフィルム(1)の硬化性絶縁層面とをラミネーター(80℃、圧力2MPa、ラインスピード 2m/分)により貼り合せて電磁波シールド性接着性フィルムを得た。
Separately, 20 parts of epoxy resin (B-1) was added to 333 parts of polyurethane polyurea resin solution (A-1) to obtain an adhesive resin composition. 120 parts of a conductive filler (Fukuda Metal Foil Powder Industry Co., Ltd .: AgXF301) is added to 353 parts of this adhesive resin composition and mixed with stirring, and the polyurethane polyurea resin (A-1) and the epoxy resin (B-1) are mixed. A curable conductive adhesive containing 100 parts of conductive filler with respect to 100 parts by weight in total was obtained.
The obtained conductive adhesive was applied to the release-treated surface of a 75 μm PET film that had been subjected to a release treatment on one side, dried at 100 ° C. for 2 minutes, and the content of metal powder per unit volume was 1 A film (2) having a curable conductive adhesive layer of .2 (g / cm 3 ) was produced. The film thickness of the curable conductive adhesive layer was about 7 μm, and the surface resistivity was 0.2 (Ω / □).
The curable conductive adhesive layer surface of the obtained film (2) and the curable insulating layer surface of the film (1) are bonded together by a laminator (80 ° C., pressure 2 MPa, line speed 2 m / min), and electromagnetic wave shielding adhesiveness. A film was obtained.
[比較例2]
実施例1で用いた導電フィラーを平均粒子径が75μmの銀粉(福田金属箔粉工業製:CE6)に変更した以外は、実施例1と同様の方法で電磁波シールド性接着性フィルムを得た。
[Comparative Example 2]
An electromagnetic wave shielding adhesive film was obtained in the same manner as in Example 1 except that the conductive filler used in Example 1 was changed to silver powder having an average particle size of 75 μm (Fukuda Metal Foil Powder Industry: CE6).
[比較例3]
片面に剥離処理を施した50μmPETフィルムの剥離処理面に、ポリウレタンポリウレア樹脂溶液(C−1)333部に対して、エポキシ樹脂(D−1)20部を加えた絶縁性樹脂を塗工し、100℃×2分乾燥させて、硬化性絶縁層を具備するフィルム(1)を作製した。
さらにフィルム(1)の硬化性絶縁性層面に、0.1μm厚みの銀蒸着をし、フィルム(2)を作製した。
[Comparative Example 3]
An insulating resin obtained by adding 20 parts of an epoxy resin (D-1) to 333 parts of a polyurethane polyurea resin solution (C-1) is applied to the release-treated surface of a 50 μm PET film subjected to a release process on one side, It was dried at 100 ° C. for 2 minutes to produce a film (1) having a curable insulating layer.
Furthermore, 0.1 μm-thick silver was deposited on the curable insulating layer surface of the film (1) to produce a film (2).
別途、ポリウレタンポリウレア樹脂溶液(A−1)333部に対して、エポキシ樹脂(B−1)20部を加えて接着樹脂組成物を得た。この接着樹脂組成物353部に対して、導電フィラー(福田金属箔粉工業製:AgXF301)120部を加えて攪拌混合し、ポリウレタンポリウレア樹脂(A−1)とエポキシ樹脂(B−1)との合計100重量部に対して、導電フィラー100部を含有する、硬化性導電性接着剤を得た。
得られた導電性接着剤を、片面に剥離処理を施した75μmのPETフィルムの剥離処理面に塗工し、100℃×2分乾燥させて、単位体積当たりの金属粉の含有量が1.2(g/cm3)の硬化性導電性接着剤層を具備するフィルム(3)を得た。硬化性導電性接着剤層の膜厚は約7μm、表面抵抗率は0.2(Ω/□)であった。
Separately, 20 parts of epoxy resin (B-1) was added to 333 parts of polyurethane polyurea resin solution (A-1) to obtain an adhesive resin composition. 120 parts of a conductive filler (Fukuda Metal Foil Powder Industry Co., Ltd .: AgXF301) is added to 353 parts of this adhesive resin composition and mixed with stirring, and the polyurethane polyurea resin (A-1) and the epoxy resin (B-1) are mixed. A curable conductive adhesive containing 100 parts of conductive filler with respect to 100 parts by weight in total was obtained.
The obtained conductive adhesive was applied to a release treatment surface of a 75 μm PET film having a release treatment on one side, dried at 100 ° C. for 2 minutes, and the content of metal powder per unit volume was 1. A film (3) having a 2 (g / cm 3 ) curable conductive adhesive layer was obtained. The film thickness of the curable conductive adhesive layer was about 7 μm, and the surface resistivity was 0.2 (Ω / □).
フィルム(3)の硬化性導電性接着剤層面とフィルム(2)の銀蒸着面とをラミネーター(100℃、圧力2MPa、ラインスピード 2m/分)により貼り合せて電磁波シールド性接着性フィルムを得た。 The curable conductive adhesive layer surface of the film (3) and the silver vapor-deposited surface of the film (2) were bonded together by a laminator (100 ° C., pressure 2 MPa, line speed 2 m / min) to obtain an electromagnetic wave shielding adhesive film. .
各実施例及び各比較例で得られた電磁波シールド性接着性フィルムについて、ポリイミドフィルム接着性、耐屈曲性、電磁波シールド性を以下の方法で評価した。結果を表1に示す。
(1)ポリイミドフィルム接着性の評価
幅10mm、長さ70mmの硬化性電磁波シールド性接着性フィルムを用意し、75μm厚みの剥離PETフィルムを剥がし、露出した硬化性導電性接着剤層に、厚さが50μmのポリイミドフィルム(東レ・デュポン社製「カプトン200EN」)を150℃、1.0MPa、30minの条件で圧着し、硬化性導電性接着剤層(I)及び硬化性絶縁層(II)を硬化させた。
圧着後、測定用の補強のために、50μm厚みの剥離PETフィルムを除去し、露出した硬化絶縁層に、ポリウレタンポリウレア系の接着シートを用い、ポリイミドフィルム(東レ・デュポン社製「カプトン200EN」)を、150℃、1MPa、30minの条件で圧着した。
23℃相対湿度50%の雰囲気下、引っ張り速度50mm/min、剥離角度90°で、硬化した導電性接着剤層とポリイミドフィルムとの間を剥離し、剥離力の中心値をポリイミドフィルム接着強度(N/cm)とした。
About the electromagnetic wave shielding adhesive film obtained by each Example and each comparative example, polyimide film adhesiveness, bending resistance, and electromagnetic wave shielding property were evaluated by the following methods. The results are shown in Table 1.
(1) Evaluation of polyimide film adhesiveness A curable electromagnetic shielding adhesive film having a width of 10 mm and a length of 70 mm was prepared, and the 75 μm-thick peeling PET film was peeled off, and the exposed curable conductive adhesive layer was thick. Is bonded to a polyimide film with a thickness of 50 μm (“Kapton 200EN” manufactured by Toray DuPont Co., Ltd.) at 150 ° C., 1.0 MPa, and 30 minutes to form a curable conductive adhesive layer (I) and a curable insulating layer (II). Cured.
After pressure bonding, the peeled PET film with a thickness of 50 μm is removed for measurement reinforcement, and a polyurethane polyurea-based adhesive sheet is used for the exposed cured insulating layer, and a polyimide film (“Kapton 200EN” manufactured by Toray DuPont) Was pressure-bonded under the conditions of 150 ° C., 1 MPa, and 30 min.
Peeling is performed between the cured conductive adhesive layer and the polyimide film at a tensile rate of 50 mm / min and a peeling angle of 90 ° in an atmosphere of 23 ° C. and a relative humidity of 50%, and the central value of the peeling force is determined as the polyimide film adhesive strength ( N / cm).
(2)耐屈曲性の評価
幅6mm、長さ120mmの硬化性電磁波シールド性接着性フィルムから75μm厚みの剥離PETフィルムを剥がし、露出した硬化性導電性接着剤層(I)を、別に作製したフレキシブルプリント配線板(厚み25μmのポリイミドフィルム上に、厚み12μmの銅箔からなる回路パターンが形成されており、さらに回路パターン上に、接着剤付きの、厚み40μmのカバーフィルムが積層されてなる配線板)のカバーフィルム面に、150℃、1MPa、30minの条件で圧着し、硬化性導電性接着剤層(I)及び硬化性絶縁層(II)を硬化させた。
50μm厚みの剥離PETフィルムを除去し、曲率半径0.38mm、荷重500g、速度180回/minの条件でMIT屈曲試験機にかけ、回路パターンが断線するまでの回数により耐屈曲性を評価した。評価基準は以下の通りである。
○:4000回以上
△:3500回以上4000回未満
×:3500回未満
(2) Evaluation of bending resistance The peeled PET film having a thickness of 6 μm and a length of 120 mm was peeled off the 75 μm-thick peeled PET film, and an exposed curable conductive adhesive layer (I) was prepared separately. Flexible printed wiring board (a circuit pattern in which a 12 μm thick copper foil pattern is formed on a 25 μm thick polyimide film, and a 40 μm thick cover film with an adhesive is laminated on the circuit pattern. The curable conductive adhesive layer (I) and the curable insulating layer (II) were cured by pressure bonding to the cover film surface of the plate) at 150 ° C. and 1 MPa for 30 minutes.
The peeled PET film having a thickness of 50 μm was removed, and subjected to an MIT bending tester under the conditions of a curvature radius of 0.38 mm, a load of 500 g, and a speed of 180 times / min, and the bending resistance was evaluated by the number of times until the circuit pattern was disconnected. The evaluation criteria are as follows.
○: 4000 times or more Δ: 3500 times or more and less than 4000 times ×: less than 3500 times
(3)電磁波シールド性
幅20cm、長さ20cmの電磁波シールド性フィルムを用意し、KEC法により電磁波シールド性(電界)測定を行った。評価基準は以下の通りである。
◎:周波数1GHzにおける電磁波シールド性が60dB以上
○:周波数1GHzにおける電磁波シールド性が50dB以上60dB未満
△:周波数1GHzにおける電磁波シールド性が40dB以上50dB未満
×:周波数1GHzにおける電磁波シールド性が40dB未満
(3) Electromagnetic shielding properties An electromagnetic shielding film having a width of 20 cm and a length of 20 cm was prepared, and electromagnetic shielding properties (electric field) were measured by the KEC method. The evaluation criteria are as follows.
A: Electromagnetic wave shielding property at a frequency of 1 GHz is 60 dB or more. O: Electromagnetic wave shielding property at a frequency of 1 GHz is 50 dB or more and less than 60 dB. Δ: An electromagnetic wave shielding property at a frequency of 1 GHz is 40 dB or more and less than 50 dB. X: An electromagnetic wave shielding property at a frequency of 1 GHz is less than 40 dB.
<表面抵抗値の測定>
表1中に表面抵抗値を記載したが、本発明においては、三菱化学アナリテック製「ロレスターGP」の四探針プローブを用いて、電磁波シールド性フィルムの表面抵抗値を測定した。
<膜厚の測定>
本発明においては、導電回路の膜厚は膜厚計(株式会社仙台ニコン製「MH−15M型」)、および透過型電子顕微鏡(日本電子株式会社)により測定した。
<Measurement of surface resistance value>
Although the surface resistance value was described in Table 1, in the present invention, the surface resistance value of the electromagnetic wave shielding film was measured using a four-point probe of “Lorestar GP” manufactured by Mitsubishi Chemical Analytech.
<Measurement of film thickness>
In the present invention, the film thickness of the conductive circuit was measured with a film thickness meter (“MH-15M type” manufactured by Sendai Nikon Corporation) and a transmission electron microscope (JEOL Ltd.).
(I) :硬化性導電性接着剤層
(II) :硬化性を有しない絶縁フィルム
(III):導電性被膜
1:剥離性フィルム
(I): Curable conductive adhesive layer (II): Insulating film not having curability (III): Conductive coating 1: Peelable film
Claims (18)
前記導電性被膜が、導電性粒子が保護物質によって被覆されてなる平均粒子径が0.001〜0.5μmの被覆導電性粒子を含む分散体から形成された被膜であり、
前記硬化性導電性接着剤層が、硬化性絶縁性樹脂と、平均粒子径が1〜50μmの金属粉とを含有する、
ことを特徴とする電磁波シールド性接着性フィルム。 An electromagnetic wave shielding adhesive film comprising an insulating film having no curability, a conductive coating, and a curable conductive adhesive layer in this order,
The conductive film is a film formed from a dispersion containing coated conductive particles having an average particle diameter of 0.001 to 0.5 μm formed by covering conductive particles with a protective substance,
The curable conductive adhesive layer contains a curable insulating resin and metal powder having an average particle diameter of 1 to 50 μm.
An electromagnetic wave shielding adhesive film characterized by that.
下記工程(1−1)〜(1−3)を含むことを特徴とする、硬化性絶縁層、導電性被膜、及び硬化性導電性接着剤層をこの順序で具備する、電磁波シールド性接着性フィルムの製造方法。
(1−1)硬化性を有しない絶縁フィルム(II)に、平均粒子径が0.001〜0.5μmの導電性粒子が保護物質によって被覆されてなる被覆導電性粒子を含む分散液を塗工し、加熱し、導電性被膜(III)を形成する工程、
(1−2)前記導電性被膜(III)上に、硬化性絶縁性樹脂と、平均粒子径が1〜50μmの金属粉とを含有する硬化性導電性接着剤を塗工し、乾燥し、硬化性導電性接着剤層(I)を形成する工程、
(1−3)前記硬化性導電性接着剤層(I)の他方の面と、剥離性フィルムとを重ね合わせる工程。 A method for producing an electromagnetic wave shielding adhesive film comprising an insulating film having no curability, a conductive coating, and a curable conductive adhesive layer in this order,
Electromagnetic wave shielding adhesiveness comprising a curable insulating layer, a conductive film, and a curable conductive adhesive layer in this order, comprising the following steps (1-1) to (1-3): A method for producing a film.
(1-1) A dispersion liquid containing coated conductive particles in which conductive particles having an average particle diameter of 0.001 to 0.5 μm are coated with a protective substance is applied to an insulating film (II) having no curability. A process of heating and forming a conductive coating (III),
(1-2) On the conductive coating (III), a curable conductive adhesive containing a curable insulating resin and a metal powder having an average particle diameter of 1 to 50 μm is applied and dried. Forming a curable conductive adhesive layer (I);
(1-3) A step of superposing the other surface of the curable conductive adhesive layer (I) on the peelable film.
下記工程(2−1)〜(2−3)を含むことを特徴とする、剥離性フィルムで硬化性導電性接着剤層面が被覆された電磁波シールド性接着性フィルムの製造方法。
(2−1)硬化性を有しない絶縁フィルム(II)に、平均粒子径が0.001〜0.5μmの導電性粒子が保護物質によって被覆されてなる被覆導電性粒子を含む分散液を塗工し、加熱し、導電性被膜(III)を形成する工程、
(2−2)剥離性フィルムの一方の面に、硬化性絶縁性樹脂と、平均粒子径が1〜50μmの金属粉とを含有する硬化性導電性接着剤を塗工し、乾燥し、硬化性導電性接着剤層(I)を形成する工程、
(2−3)前記硬化性導電性接着剤層(I)と、前記導電性被膜(III)とを重ね合わせる工程。 A method for producing an electromagnetic wave shielding adhesive film comprising an insulating film having no curability, a conductive coating, and a curable conductive adhesive layer in this order,
The manufacturing method of the electromagnetic wave shielding adhesive film with which the curable conductive adhesive layer surface was coat | covered with the peelable film characterized by including the following process (2-1)-(2-3).
(2-1) A dispersion liquid containing coated conductive particles in which conductive particles having an average particle diameter of 0.001 to 0.5 μm are coated with a protective substance is applied to the insulating film (II) having no curability. A process of heating and forming a conductive coating (III),
(2-2) One side of the peelable film is coated with a curable conductive adhesive containing a curable insulating resin and a metal powder having an average particle diameter of 1 to 50 μm, dried and cured. Forming the conductive conductive adhesive layer (I),
(2-3) A step of overlaying the curable conductive adhesive layer (I) and the conductive coating (III).
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JP2013093518A (en) * | 2011-10-27 | 2013-05-16 | Fujimori Kogyo Co Ltd | Manufacturing method of electromagnetic wave shield material for fpc |
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JP2012131948A (en) * | 2010-12-24 | 2012-07-12 | Sumitomo Bakelite Co Ltd | Resin composition, prepreg, laminate plate, resin sheet, printed wiring board, and semiconductor device |
JP2013093518A (en) * | 2011-10-27 | 2013-05-16 | Fujimori Kogyo Co Ltd | Manufacturing method of electromagnetic wave shield material for fpc |
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