JP6684712B2 - Resin-containing sheet, and structure and wiring board using the same - Google Patents
Resin-containing sheet, and structure and wiring board using the same Download PDFInfo
- Publication number
- JP6684712B2 JP6684712B2 JP2016538237A JP2016538237A JP6684712B2 JP 6684712 B2 JP6684712 B2 JP 6684712B2 JP 2016538237 A JP2016538237 A JP 2016538237A JP 2016538237 A JP2016538237 A JP 2016538237A JP 6684712 B2 JP6684712 B2 JP 6684712B2
- Authority
- JP
- Japan
- Prior art keywords
- resin
- containing sheet
- bis
- elastic modulus
- fiber
- 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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- 229920005989 resin Polymers 0.000 title claims description 186
- 239000011347 resin Substances 0.000 title claims description 186
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- 239000000853 adhesive Substances 0.000 claims description 81
- 239000000203 mixture Substances 0.000 claims description 68
- 230000001070 adhesive effect Effects 0.000 claims description 66
- 239000000463 material Substances 0.000 claims description 56
- 238000003860 storage Methods 0.000 claims description 56
- 239000003795 chemical substances by application Substances 0.000 claims description 53
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- 239000004760 aramid Substances 0.000 claims description 21
- 229920003235 aromatic polyamide Polymers 0.000 claims description 21
- 230000009477 glass transition Effects 0.000 claims description 19
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- 239000000543 intermediate Substances 0.000 description 31
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 8
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- 229910000679 solder Inorganic materials 0.000 description 7
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- 125000003118 aryl group Chemical group 0.000 description 5
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 5
- 230000008859 change Effects 0.000 description 5
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- 229910052757 nitrogen Inorganic materials 0.000 description 5
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
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- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
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- 239000004700 high-density polyethylene Substances 0.000 description 4
- 238000005470 impregnation Methods 0.000 description 4
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 229920000069 polyphenylene sulfide Polymers 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 229960000834 vinyl ether Drugs 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 3
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 3
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 3
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 3
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 3
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
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- UMHKOAYRTRADAT-UHFFFAOYSA-N [hydroxy(octoxy)phosphoryl] octyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OP(O)(=O)OCCCCCCCC UMHKOAYRTRADAT-UHFFFAOYSA-N 0.000 description 3
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/248—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using pre-treated fibres
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
- H05K1/0366—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement reinforced, e.g. by fibres, fabrics
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2300/00—Characterised by the use of unspecified polymers
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Manufacturing & Machinery (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Laminated Bodies (AREA)
- Reinforced Plastic Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
本発明は、優れた力学強度、弾性率および密着性を有し、電子機器用の配線板等に好適な樹脂含有シート、並びに、それを用いた構造体および配線板に関する。 TECHNICAL FIELD The present invention relates to a resin-containing sheet having excellent mechanical strength, elastic modulus, and adhesiveness, which is suitable for a wiring board for electronic devices and the like, and a structure and a wiring board using the resin-containing sheet.
電子機器用の配線板としては、一般に、ガラス繊維やアラミド繊維、セルロース繊維などからなる基材にエポキシ等の樹脂を含浸させて得られるプリプレグ(半硬化状態の樹脂絶縁層)を、銅等の金属箔に密着させ、エッチング法で回路を形成したものが用いられている。また、配線板には、部品実装時におけるはんだの流出を防止するために、ソルダーレジストが設けられている。これらプリプレグやソルダーレジスト等の配線板材料は、金属箔表面や回路形成された配線板表面に対し隙間なく密着するように、加熱加圧しながら密着させる必要があり、その際の密着性が重要となる。また、配線板には、実装信頼性を高めるために高強度(高弾性率)であることが望まれており、その構成部材であるプリプレグやソルダーレジストについても、同様に高弾性率化が図られている。 As a wiring board for electronic devices, generally, a prepreg (semi-cured resin insulation layer) obtained by impregnating a substrate made of glass fiber, aramid fiber, cellulose fiber or the like with a resin such as epoxy is used. The one in which a circuit is formed by an etching method, which is in close contact with a metal foil, is used. In addition, the wiring board is provided with a solder resist in order to prevent the outflow of solder when mounting the components. Wiring board materials such as these prepregs and solder resists need to be adhered while heating and pressing so that they adhere closely to the metal foil surface or the circuit board formed circuit board without any gaps, and the adhesion at that time is important. Become. In addition, the wiring board is required to have high strength (high elastic modulus) in order to improve mounting reliability, and the prepreg and solder resist, which are its constituent members, are also required to have high elastic modulus. Has been.
配線板材料に関する従来技術として、例えば、特許文献1には、絶縁信頼性および配線との応力緩和の両機能を得るために、コア層の両面に異なる強度(弾性率)の樹脂層を設けたプリプレグが記載されている。しかし、この技術は、コア層の両面に異なる樹脂組成物の層を設けるものであり、また、密着性に有用であるとの開示はない。また、特許文献2には、所定の弾性率を有するプリプレグが記載されている。この技術はプリプレグシートと回路基板との仮固定を目的とし、弾性率を組成物によって制御しているものである。 As a conventional technique relating to a wiring board material, for example, in Patent Document 1, resin layers having different strengths (elastic moduli) are provided on both surfaces of a core layer in order to obtain both functions of insulation reliability and stress relaxation with wiring. A prepreg is described. However, this technique provides layers of different resin compositions on both surfaces of the core layer, and there is no disclosure that it is useful for adhesion. Further, Patent Document 2 describes a prepreg having a predetermined elastic modulus. This technique aims to temporarily fix the prepreg sheet and the circuit board, and the elastic modulus is controlled by the composition.
さらに、特許文献3には、プリプレグ中に2種の樹脂組成物を用いる技術が開示されている。このプリプレグにおいては2種の樹脂組成物を表面側ほど弾性率が大きくなるように偏在させている。さらにまた、特許文献4には、金属箔との接着性を改良するためにプリプレグ表面に接着層を設ける技術が記載されている。 Further, Patent Document 3 discloses a technique of using two kinds of resin compositions in a prepreg. In this prepreg, two kinds of resin compositions are unevenly distributed so that the elastic modulus increases toward the surface side. Furthermore, Patent Document 4 describes a technique of providing an adhesive layer on the surface of the prepreg in order to improve the adhesiveness to the metal foil.
しかしながら、上記従来のプリプレグでは、十分な力学強度と密着性を有することができなかった。 However, the above-mentioned conventional prepreg cannot have sufficient mechanical strength and adhesiveness.
そこで、本発明の目的は、力学強度を向上させつつ、基板との密着性についても向上した樹脂含有シート、並びに、それを用いた構造体および配線板を提供することにある。 Therefore, an object of the present invention is to provide a resin-containing sheet having improved mechanical strength and improved adhesion to a substrate, and a structure and a wiring board using the same.
本発明者らは、上記課題を解決するために鋭意検討した結果、以下のことを見出した。
すなわち、一般に、各種繊維状材料からなる織布や不織布においては、繊維同士が絡み合いや相互作用により集合体を形成している。よって、図2(a)に示すように、このような繊維21の集合体に対し一方向に張力Tをかけると、繊維21同士が接点Pで滑って、矢印Dの方向に繊維21同士が引き離され、集合体には、ほつれが生じ、最終的には破断することになる。この点、織布の場合は、繊維方向の引っ張りに対する強度はある程度高いが、繊維方向と異なる方向(斜め方向)の引っ張りに対する強度は低い。また、不織布の場合、どの方向においても、引っ張りに対する強度は低い。As a result of earnest studies to solve the above problems, the present inventors have found out the following.
That is, generally, in a woven fabric or a non-woven fabric made of various fibrous materials, the fibers are entangled or interacted with each other to form an aggregate. Therefore, as shown in FIG. 2A, when tension T is applied in one direction to such an aggregate of
前述したように、配線板には、ガラスクロス等の織布やアラミド繊維等よりなる不織布と樹脂とからなるプリプレグのような樹脂含有シートが用いられるので、配線板の強度を確保するためには、繊維の集合体において、繊維同士の滑りを防止することが重要となる。一方で、前述したように、樹脂含有シートには、金属箔表面や配線板表面に対する良好な密着性も要求される。 As described above, since the wiring board uses a resin-containing sheet such as a woven cloth such as glass cloth or a non-woven fabric made of aramid fiber and the like and a prepreg made of a resin, it is necessary to secure the strength of the wiring board. In a fiber assembly, it is important to prevent the fibers from slipping. On the other hand, as described above, the resin-containing sheet is also required to have good adhesion to the surface of the metal foil or the surface of the wiring board.
上記検討の結果、本発明者らは、以下の構成とすることにより、力学強度と密着性とのバランスをとることができることを見出した。
すなわち、本発明の樹脂含有シートは、繊維基材と、前記繊維基材中の繊維同士を固着する固着剤と、前記繊維基材と固着剤とに接する樹脂と、を有し、前記固着剤の貯蔵弾性率が、前記樹脂の貯蔵弾性率よりも高いことを特徴とするものである。As a result of the above investigation, the present inventors have found that the mechanical strength and the adhesiveness can be balanced by the following constitution.
That is, the resin-containing sheet of the present invention has a fibrous base material, a fixing agent that fixes the fibers in the fibrous base material to each other, and a resin that contacts the fibrous base material and the fixing agent. The storage elastic modulus of is higher than the storage elastic modulus of the resin.
本発明において、前記固着剤のガラス転移温度は、前記樹脂のガラス転移温度または軟化温度よりも高いことが好ましい。本発明の樹脂含有シートは、前記繊維基材の繊維同士を固着剤組成物により固着させた後、該固着された繊維基材に樹脂組成物を含浸して得ることができる。この場合、前記固着剤組成物の粘度は、1Pa・s以下であることが好ましい。また、本発明の樹脂含有シートにおいては、前記繊維基材が織布または不織布を含むことが好ましい。 In the present invention, the glass transition temperature of the fixing agent is preferably higher than the glass transition temperature or softening temperature of the resin. The resin-containing sheet of the present invention can be obtained by fixing the fibers of the fiber base material to each other with a fixing agent composition, and then impregnating the fixed fiber base material with the resin composition. In this case, the viscosity of the adhesive composition is preferably 1 Pa · s or less. Further, in the resin-containing sheet of the present invention, it is preferable that the fiber base material includes a woven fabric or a non-woven fabric.
本発明の構造体は、上記本発明の樹脂含有シートを、基板に密着させて得られることを特徴とするものである。 The structure of the present invention is characterized by being obtained by bringing the resin-containing sheet of the present invention into close contact with a substrate.
さらに、本発明の配線板は、上記本発明の構造体を有することを特徴とするものである。 Furthermore, the wiring board of the present invention is characterized by having the above-mentioned structure of the present invention.
本発明によれば、力学強度を向上しつつ、基板との密着性を向上した樹脂含有シートを得ることが可能となった。すなわち、本発明においては、繊維基材中の繊維同士を固着する固着剤の貯蔵弾性率を、繊維基材と固着剤とに接する樹脂の貯蔵弾性率よりも高くしたことで、高強度・高弾性率化を図るとともに、密着性も向上した樹脂含有シートを得るための材料の条件を見出したものである。これは、配線板用の樹脂絶縁材には高強度化が要求されているが、例えば、ポリイミド等の高弾性率材料を用いると金属箔等に対する密着性が悪化するものであるところ、本発明においては、高弾性率化を実現しつつ、この密着性の問題を解決するものである。 According to the present invention, it is possible to obtain a resin-containing sheet having improved mechanical strength and improved adhesion to a substrate. That is, in the present invention, the storage elastic modulus of the adhesive agent for adhering the fibers in the fiber base material is made higher than the storage elastic modulus of the resin in contact with the fiber base material and the adhesive agent, so that high strength and high strength are achieved. The inventors have found the conditions of materials for obtaining a resin-containing sheet having an improved elastic modulus and improved adhesion. This requires that the resin insulating material for the wiring board have high strength. For example, when a high elastic modulus material such as polyimide is used, the adhesion to a metal foil or the like is deteriorated. In (1), the problem of this adhesiveness is solved while realizing a high elastic modulus.
以下、本発明の実施の形態について、図面を参照しつつ詳細に説明する。
図1に、本発明の樹脂含有シートの構造を示す説明図を示す。本発明の樹脂含有シートは、主として繊維成分と樹脂成分から形成されるシート状体であり、図示するように、繊維基材11と、繊維基材11中の繊維1同士を固着する固着剤2と、繊維基材11と固着剤2とに接する樹脂3と、を有している。なお、図中の符号Sは、繊維基材11内で固着剤2および樹脂3のいずれも含浸されていない空間を示す。本発明の樹脂含有シートにおいては、繊維基材11を構成する繊維1と、固着剤2と、樹脂3とが、全体として1つの層を形成しているものといえる。本発明の樹脂含有シートにおいては、繊維1同士を固着する固着剤2の貯蔵弾性率が、いずれかの温度において、樹脂3の貯蔵弾性率よりも高い点が重要である。Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings.
FIG. 1 shows an explanatory view showing the structure of the resin-containing sheet of the present invention. The resin-containing sheet of the present invention is a sheet-like body mainly composed of a fiber component and a resin component, and as shown in the figure, a
すなわち、本発明者らは鋭意検討の結果、樹脂含有シートに含まれる樹脂成分の役割には2つあり、1つは、繊維同士の滑りを抑制して、樹脂含有シートを高強度および高弾性率化するための固着剤としての役割であり、もう1つは、絶縁樹脂層と金属箔表面等とを密着させる役割であることを見出した。かかる観点から、本発明者らはさらに検討した結果、樹脂含有シートに含まれる樹脂成分の2つの役割を、高強度の確保については固着剤に、密着性の確保については樹脂に、それぞれ分担させて、これら固着剤と樹脂との貯蔵弾性率の関係を規定することで、これら両性能をともに良好に確保できることを見出したものである。このように、樹脂成分の役割を2つに分けて、高弾性率と良好な密着性とを両立させた技術は、従来、知られていない。 That is, as a result of earnest studies by the present inventors, the role of the resin component contained in the resin-containing sheet is two, and one is to suppress slippage between fibers and to make the resin-containing sheet have high strength and high elasticity. It has been found that it has a role as a fixing agent for rationalization, and the other has a role of bringing the insulating resin layer into close contact with the metal foil surface and the like. From this point of view, as a result of further study by the present inventors, the two roles of the resin component contained in the resin-containing sheet are shared by the adhesive for securing high strength and the resin for securing adhesiveness. Then, it has been found that both of these performances can be satisfactorily ensured by defining the relationship between the storage elastic modulus of the adhesive and the resin. As described above, a technique in which the role of the resin component is divided into two and the high elastic modulus and the good adhesiveness are compatible with each other has not heretofore been known.
図2(b)に示すように、本発明を概念的に説明すると、繊維基材11に含まれる繊維1の接点Pを固着剤2により固着したことで、一方向に張力Tをかけた場合でも、接点Pで滑りが生じないので、繊維基材11を高強度・高弾性率化することができる。さらに、繊維基材11と固着剤2に接するように樹脂3を含浸することで、樹脂含有シートとしての、良好な接着性も得ることができるものである。よって、本発明の樹脂含有シートによれば、繊維基材11に対し要求される高い弾性率を固着剤2により確保しつつ、基板等に対する密着性を樹脂3により確保することができ、単にポリイミド等の高弾性率材料を用いることによっては得られなかった、高強度と良好な密着性との双方を兼ね備えた樹脂含有シートを得ることが可能となった。
As shown in FIG. 2B, the present invention is conceptually described. In the case where the contact point P of the fiber 1 included in the
[繊維基材]
本発明に係る繊維基材11は、繊維1の集合体よりなる。繊維1としては、集合体を形成し、織布または不織布を製造できるものであれば特に限定されず、主として天然繊維や化学繊維を使用することができる。繊維1の具体例のうち、天然繊維としては、ガラス繊維、セルロース繊維、岩石繊維、金属繊維、炭素繊維、ロックウール等が挙げられ、化学繊維としては、アラミド、ナイロン、ビニロン、ビニリデン、ポリエステル、ポリオレフィン(ポリエチレンテレフタレート、変性ポリエチレンテレフタレート、ポリエチレン、ポリプロピレン等)、ポリウレタン、アクリル、ポリ塩化ビニル、ポリエーテルエーテルケトン、ポリアミドイミド、ポリフェニレンスルフィド、ポリエーテルイミド、ポリテトラフルオロエチレン、アセテート、トリアセテート、プロミックス、レーヨン、キュプラ、ポリノジックレーヨン、リヨセル、テンセル等が挙げられ、これらのうちの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。また、その製法、繊維含有量(繊維配合率)、繊維径、繊維長、質量(坪量)・密度(比重)、厚み、および、織布の織組織については、目的に応じて適宜選択することができる。繊維基材11としては、上記のうちでも、固着剤との親和性の観点から、ガラス繊維、セルロース繊維、アラミド繊維が好ましい。[Fiber substrate]
The
本発明においては、特には、繊維基材11として織布を用いることが好ましく、織りを加えることにより、元々強度の低い繊維であっても高強度化できるメリットが得られる。また、本発明においては、繊維基材11として、元々高強度であるガラス繊維ではなく、強度が低い有機繊維を用いた場合であっても、貯蔵弾性率の高い固着剤を用いることで高強度化できるという利点もある。
In the present invention, it is particularly preferable to use a woven fabric as the
[固着剤組成物]
固着剤2を形成する固着剤組成物としては、繊維1に付着して、繊維1同士を固着させることができるものであればよく、繊維同士が互いに接し合う接点部のみを固着するものであっても、繊維1の全体を被覆して固着するものであってもよい。固着剤組成物の使用量としては、繊維1同士を固着させることができ、密着性に悪影響が及ばない程度の量であればよく、繊維1を固着剤2により固着させた集合体において、有機溶媒を除いた固形分で、繊維1と固着剤2との体積比が99:1〜50:50の範囲、特には、99:1〜60:40の範囲であることが好ましい。繊維1と固着剤2との体積比がこの範囲であると、繊維1同士が固着剤により十分に固着されて所望の高強度が得られるものとなるとともに、その後の樹脂3の含浸により良好な密着性が確保できるものとなり、好ましい。特には、固着剤2の使用量は、固着剤2の適用前後において、繊維基材11の膜厚が実質的に変化しない程度の量であることが好ましい。ここで、膜厚が実質的に変化しないとは、繊維基材11が固着剤組成物の溶剤成分等により膨潤して見かけ上厚みを増すような場合を膜厚の変化に含まないとの意味である。また、固着剤組成物は、繊維に付着させる際に液体であることが好ましく、温度や圧力を変えることで液体にして用いることができるものであってもよい。特には、固着剤組成物の、25℃にてE型粘度計におけるローター回転数5rpmで測定した粘度が1Pa・s以下、例えば、1〜0.0001Pa・sであることが好ましく、これにより、繊維1の集合体の内部まで、固着剤組成物を含浸させることができ、繊維同士を、より確実に固着させることができる。[Adhesive composition]
The adhesive composition for forming the adhesive 2 may be any adhesive that can adhere to the fibers 1 and adhere the fibers 1 to each other, and only adheres to the contact portions where the fibers contact each other. Alternatively, the entire fiber 1 may be covered and fixed. The amount of the adhesive composition used may be such that the fibers 1 can be adhered to each other and the adhesiveness is not adversely affected. In the aggregate in which the fibers 1 are adhered by the adhesive 2, It is preferable that the volume ratio of the fiber 1 to the fixing agent 2 is 99: 1 to 50:50, particularly 99: 1 to 60:40, in terms of solid content excluding the solvent. When the volume ratio of the fiber 1 to the adhesive agent 2 is within this range, the fibers 1 are sufficiently adhered to each other by the adhesive agent, and a desired high strength is obtained, and the subsequent impregnation with the resin 3 is preferable. It is preferable because the adhesion can be secured. In particular, the amount of the adhesive 2 used is preferably such that the film thickness of the
また、固着剤組成物は、熱または光により硬化するものを用いる。ここでいう硬化とは、熱または光のエネルギーにより液体から固体に化学変化することを意味する。固着剤組成物としては、その用途に応じて、慣用の成分を用いることができ、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。固着剤組成物に用いられる慣用の成分としては、例えば、熱硬化性樹脂、硬化剤、熱硬化触媒、光硬化性樹脂、光重合開始剤、光酸発生剤、光塩基発生剤、有機溶媒などが挙げられ、具体的には、以下に示すものが使用可能である。 Further, as the adhesive composition, one which is cured by heat or light is used. The curing here means a chemical change from a liquid to a solid by heat or light energy. As the adhesive composition, a commonly used component can be used depending on the application, and one kind can be used alone, or two or more kinds can be used in combination. Examples of conventional components used in the adhesive composition include thermosetting resins, curing agents, thermosetting catalysts, photocurable resins, photopolymerization initiators, photoacid generators, photobase generators, and organic solvents. And specifically, the following can be used.
(熱硬化性樹脂)
熱硬化性樹脂は、加熱により硬化して電気絶縁性を示す樹脂であればよく、例えば、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、ビスフェノールE型エポキシ樹脂、ビスフェノールM型エポキシ樹脂、ビスフェノールP型エポキシ樹脂、ビスフェノールZ型エポキシ樹脂などのビスフェノール型エポキシ樹脂、ビスフェノールA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、クレゾールノボラックエポキシ樹脂などのノボラック型エポキシ樹脂、ビフェニル型エポキシ樹脂、ビフェニルアラルキル型エポキシ樹脂、アリールアルキレン型エポキシ樹脂、テトラフェニロールエタン型エポキシ樹脂、ナフタレン型エポキシ樹脂、アントラセン型エポキシ樹脂、フェノキシ型エポキシ樹脂、ジシクロペンタジエン型エポキシ樹脂、ノルボルネン型エポキシ樹脂、アダマンタン型エポキシ樹脂、フルオレン型エポキシ樹脂、グリシジルメタアクリレート共重合系エポキシ樹脂、シクロヘキシルマレイミドとグリシジルメタアクリレートとの共重合エポキシ樹脂、エポキシ変性のポリブタジエンゴム誘導体、CTBN変性エポキシ樹脂、トリメチロールプロパンポリグリシジルエーテル、フェニル−1,3−ジグリシジルエーテル、ビフェニル−4,4’−ジグリシジルエーテル、1,6−ヘキサンジオールジグリシジルエーテル、エチレングリコールまたはプロピレングリコールのジグリシジルエーテル、ソルビトールポリグリシジルエーテル、トリス(2,3−エポキシプロピル)イソシアヌレート、トリグリシジルトリス(2−ヒドロキシエチル)イソシアヌレート、フェノールノボラック樹脂、クレゾールノボラック樹脂、ビスフェノールAノボラック樹脂などのノボラック型フェノール樹脂、未変性のレゾールフェノール樹脂、桐油、アマニ油、クルミ油などで変性した油変性レゾールフェノール樹脂などのレゾール型フェノール樹脂などのフェノール樹脂、フェノキシ樹脂、尿素(ユリア)樹脂、メラミン樹脂などのトリアジン環含有樹脂、不飽和ポリエステル樹脂、ビスマレイミド樹脂、ジアリルフタレート樹脂、シリコーン樹脂、ベンゾオキサジン環を有する樹脂、ノルボルネン系樹脂、シアネート樹脂、イソシアネート樹脂、ウレタン樹脂、ベンゾシクロブテン樹脂、マレイミド樹脂、ビスマレイミドトリアジン樹脂、ポリアゾメチン樹脂、ポリイミド樹脂等が挙げられる。これらの中でも特に、エポキシ樹脂やポリイミド樹脂が、絶縁層としての信頼性が優れているために好ましい。(Thermosetting resin)
The thermosetting resin may be any resin that is cured by heating and exhibits electrical insulation, and examples thereof include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, bisphenol E type epoxy resin, and bisphenol M. Type epoxy resin, bisphenol P type epoxy resin, bisphenol Z type epoxy resin and other bisphenol type epoxy resin, bisphenol A novolac type epoxy resin, phenol novolac type epoxy resin, cresol novolac epoxy resin and other novolac type epoxy resin, biphenyl type epoxy resin , Biphenyl aralkyl type epoxy resin, aryl alkylene type epoxy resin, tetraphenylol ethane type epoxy resin, naphthalene type epoxy resin, anthracene type epoxy resin, Enoxy type epoxy resin, dicyclopentadiene type epoxy resin, norbornene type epoxy resin, adamantane type epoxy resin, fluorene type epoxy resin, glycidyl methacrylate copolymer epoxy resin, cyclohexyl maleimide and glycidyl methacrylate copolymer epoxy resin, epoxy Modified polybutadiene rubber derivative, CTBN modified epoxy resin, trimethylolpropane polyglycidyl ether, phenyl-1,3-diglycidyl ether, biphenyl-4,4'-diglycidyl ether, 1,6-hexanediol diglycidyl ether, ethylene Diglycidyl ether of glycol or propylene glycol, sorbitol polyglycidyl ether, tris (2,3-epoxypropyl) isocyanurate, Glycidyl tris (2-hydroxyethyl) isocyanurate, phenol novolac resin, cresol novolac resin, bisphenol A novolac resin and other novolac type phenolic resins, unmodified resole phenolic resin, tung oil, linseed oil, walnut oil, etc. Phenol resin such as resole phenolic resin such as resole phenolic resin, phenoxy resin, urea (urea) resin, triazine ring-containing resin such as melamine resin, unsaturated polyester resin, bismaleimide resin, diallyl phthalate resin, silicone resin, benzoxazine Ring-containing resin, norbornene-based resin, cyanate resin, isocyanate resin, urethane resin, benzocyclobutene resin, maleimide resin, bismaleimide triazine resin, polyazo Chin resins, and polyimide resins. Of these, epoxy resin and polyimide resin are particularly preferable because they have excellent reliability as an insulating layer.
エポキシ樹脂としては、1分子中に少なくとも2つのエポキシ基を有する公知慣用の多官能エポキシ樹脂が使用できる。エポキシ樹脂は、液状であってもよく、固形または半固形であってもよい。中でも、特に、ビスフェノールA型エポキシ樹脂、ナフタレン型エポキシ樹脂、フェノールノボラック型エポキシ樹脂またはそれらの混合物が好ましい。これらのエポキシ樹脂は、1種を単独で用いてもよく、2種以上を組み合わせて用いてもよい。エポキシ樹脂としては、具体的には例えば、三菱化学(株)製のjER828等が挙げられるが、これに限られるものではない。 As the epoxy resin, a known and commonly used polyfunctional epoxy resin having at least two epoxy groups in one molecule can be used. The epoxy resin may be liquid, solid or semi-solid. Among them, bisphenol A type epoxy resin, naphthalene type epoxy resin, phenol novolac type epoxy resin or a mixture thereof is particularly preferable. These epoxy resins may be used alone or in combination of two or more. Specific examples of the epoxy resin include jER828 manufactured by Mitsubishi Chemical Co., Ltd., but the epoxy resin is not limited thereto.
エポキシ樹脂を用いて硬化物を形成する場合には、エポキシ樹脂の他に、硬化剤を含有することが好ましい。硬化剤としては、2−エチル−4−メチルイミダゾール(2E4MZ)、2−フェニルイミダゾール(2PZ)、2−フェニル−4−メチル−5−ヒドロキシメチルイミダゾール(2P4MHZ)等のイミダゾール系硬化剤、ジエチレントリアミン、トリエチレンテトラミン、テトラエチレンペンタミン、ペンタエチレンヘキサミン、メタキシレンジアミン、イソホロンジアミン、ノルボルネンジアミン、1,3−ビスアミノメチルシクロヘキサン、N−アミノエチルピペラジン等のアミン系硬化剤、ポリアミド、ビニルフェノール、アラルキル型フェノール樹脂、フェノールフェニルアラルキル樹脂、フェノールビフェニルアラルキル樹脂等のフェノール系硬化剤、無水フタル酸、テトラヒドロフタル酸、ヘキサヒドロフタル酸、メチルテトラヒドロフタル酸、メチルヘキサヒドロフタル酸、無水メチルナジック酸、ドデシル無水コハク酸、無水クロレンディック酸、無水ピロメリット酸、ベンゾフェノンテトラカルボン酸無水物、エチレングリコールビス(アンヒドロトリメート)、メチルシクロヘキセンテトラカルボン酸無水物等の酸無水物系硬化剤、シアネートエステル樹脂、活性エステル樹脂、脂肪族または芳香族の一級または二級アミン、ポリアミド樹脂、ポリメルカプト化合物などの公知の硬化剤を使用できる。硬化剤の配合量は、上記エポキシ樹脂100質量部に対して、好ましくは0.1〜150質量部、より好ましくは0.5〜100質量部である。硬化剤の配合量を、0.1質量部以上とすることで樹脂組成物を十分に硬化させることができ、150質量部以下とすることで、配合量に見合った効果を効率的に得ることができる。 When a cured product is formed using an epoxy resin, it is preferable to contain a curing agent in addition to the epoxy resin. Examples of the curing agent include 2-ethyl-4-methylimidazole (2E4MZ), 2-phenylimidazole (2PZ), 2-phenyl-4-methyl-5-hydroxymethylimidazole (2P4MHZ) and other imidazole-based curing agents, diethylenetriamine, Amine curing agents such as triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, metaxylenediamine, isophoronediamine, norbornenediamine, 1,3-bisaminomethylcyclohexane, N-aminoethylpiperazine, polyamide, vinylphenol, aralkyl. Type phenol resin, phenol phenyl aralkyl resin, phenol biphenyl aralkyl resin and other phenolic curing agents, phthalic anhydride, tetrahydrophthalic acid, hexahydrophthalic acid, methyl terephthalate Lahydrophthalic acid, methyl hexahydrophthalic acid, methyl nadic acid anhydride, dodecyl succinic anhydride, chlorendic acid anhydride, pyromellitic dianhydride, benzophenone tetracarboxylic acid anhydride, ethylene glycol bis (anhydrotrimate), methyl cyclohexene tetra A known curing agent such as an acid anhydride-based curing agent such as a carboxylic acid anhydride, a cyanate ester resin, an active ester resin, an aliphatic or aromatic primary or secondary amine, a polyamide resin, or a polymercapto compound can be used. The compounding amount of the curing agent is preferably 0.1 to 150 parts by mass, more preferably 0.5 to 100 parts by mass with respect to 100 parts by mass of the epoxy resin. When the compounding amount of the curing agent is 0.1 part by mass or more, the resin composition can be sufficiently cured, and when the compounding amount is 150 parts by mass or less, an effect commensurate with the compounding amount can be efficiently obtained. You can
また、熱硬化触媒としては、例えば、イミダゾール、2−メチルイミダゾール、2−エチルイミダゾール、2−エチル−4−メチルイミダゾール、2−フェニルイミダゾール、4−フェニルイミダゾール、1−シアノエチル−2−フェニルイミダゾール、1−(2−シアノエチル)−2−エチル−4−メチルイミダゾール等のイミダゾール誘導体;ジシアンジアミド、ベンジルジメチルアミン、4−(ジメチルアミノ)−N,N−ジメチルベンジルアミン、4−メトキシ−N,N−ジメチルベンジルアミン、4−メチル−N,N−ジメチルベンジルアミン等のアミン化合物、アジピン酸ジヒドラジド、セバシン酸ジヒドラジド等のヒドラジン化合物;トリフェニルホスフィン等のリン化合物などが挙げられる。また、グアナミン、アセトグアナミン、ベンゾグアナミン、メラミン、2,4−ジアミノ−6−メタクリロイルオキシエチル−S−トリアジン、2−ビニル−2,4−ジアミノ−S−トリアジン、2−ビニル−4,6−ジアミノ−S−トリアジン・イソシアヌル酸付加物、2,4−ジアミノ−6−メタクリロイルオキシエチル−S−トリアジン・イソシアヌル酸付加物等のS−トリアジン誘導体を用いることもできる。 Further, as the thermosetting catalyst, for example, imidazole, 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 4-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, Imidazole derivatives such as 1- (2-cyanoethyl) -2-ethyl-4-methylimidazole; dicyandiamide, benzyldimethylamine, 4- (dimethylamino) -N, N-dimethylbenzylamine, 4-methoxy-N, N- Examples thereof include amine compounds such as dimethylbenzylamine and 4-methyl-N, N-dimethylbenzylamine, hydrazine compounds such as adipic acid dihydrazide and sebacic acid dihydrazide, and phosphorus compounds such as triphenylphosphine. Also, guanamine, acetoguanamine, benzoguanamine, melamine, 2,4-diamino-6-methacryloyloxyethyl-S-triazine, 2-vinyl-2,4-diamino-S-triazine, 2-vinyl-4,6-diamino. S-triazine derivatives such as -S-triazine / isocyanuric acid adduct and 2,4-diamino-6-methacryloyloxyethyl-S-triazine / isocyanuric acid adduct can also be used.
ポリイミド樹脂としては、一般的に知られている芳香族多価カルボン酸無水物またはその誘導体と芳香族ジアミンとの合成反応によって、ポリアミック酸(ポリイミド前駆体)を経由して得られるものと、既に有機溶媒にポリアミック酸組成物が溶解された状態の、いわゆるポリイミドワニスとして上市されているものが挙げられる。 Examples of the polyimide resin include those obtained through a polyamic acid (polyimide precursor) by a synthetic reaction of a generally known aromatic polyvalent carboxylic acid anhydride or its derivative and an aromatic diamine, Examples include so-called polyimide varnishes in the market, in which a polyamic acid composition is dissolved in an organic solvent.
芳香族多価カルボン酸無水物の具体例としては、例えば、ピロメリット酸二無水物、3,3’,4,4’−ベンゾフェノンテトラカルボン酸二無水物、2,2’,3,3’−ベンゾフェノンテトラカルボン酸二無水物、3,3’,4,4’−ビフェニルテトラカルボン酸二無水物、2,2’,3,3’−ビフェニルテトラカルボン酸二無水物、2,2−ビス(2,3−ジカルボキシフェニル)プロパン二無水物、ビス(3,4−ジカルボキシフェニル)エーテル二無水物、ビス(3,4−ジカルボキシフェニル)スルホン二無水物、1,1−ビス(2,3−ジカルボキシフェニル)エタン二無水物、ビス(2,3−ジカルボキシフェニル)メタン二無水物、ビス(3,4−ジカルボキシフェニル)メタン二無水物、2,2−ビス(3,4−ジカルボキシルフェニル)−1,1,1,3,3,3−ヘキサフルオロプロパン二無水物、2,3,6,7−ナフタレンテトラカルボン酸二無水物、1,4,5,8−ナフタレンテトラカルボン酸二無水物、1,2,5,6−ナフタレンテトラカルボン酸二無水物、1,2,3,4−ベンゼンテトラカルボン酸二無水物、3,4,9,10−ペリレンテトラカルボン酸二無水物、2,3,6,7−アントラセンテトラカルボン酸二無水物、1,2,7,8−フェナントレンテトラカルボン酸二無水物等が挙げられる。これらは単独または2種以上混合して用いられる。これらの中でも、特に、少なくとも成分の1つとして、ピロメリット酸二無水物を用いることが好ましい。 Specific examples of the aromatic polycarboxylic acid anhydride include, for example, pyromellitic dianhydride, 3,3 ′, 4,4′-benzophenonetetracarboxylic dianhydride, 2,2 ′, 3,3 ′. -Benzophenone tetracarboxylic dianhydride, 3,3 ', 4,4'-biphenyltetracarboxylic dianhydride, 2,2', 3,3'-biphenyltetracarboxylic dianhydride, 2,2-bis (2,3-Dicarboxyphenyl) propane dianhydride, bis (3,4-dicarboxyphenyl) ether dianhydride, bis (3,4-dicarboxyphenyl) sulfone dianhydride, 1,1-bis ( 2,3-dicarboxyphenyl) ethane dianhydride, bis (2,3-dicarboxyphenyl) methane dianhydride, bis (3,4-dicarboxyphenyl) methane dianhydride, 2,2-bis (3 , 4-di Ruboxylphenyl) -1,1,1,3,3,3-hexafluoropropane dianhydride, 2,3,6,7-naphthalenetetracarboxylic dianhydride, 1,4,5,8-naphthalenetetracarboxylic acid Acid dianhydride, 1,2,5,6-naphthalenetetracarboxylic dianhydride, 1,2,3,4-benzenetetracarboxylic dianhydride, 3,4,9,10-perylenetetracarboxylic dianhydride An anhydride, 2,3,6,7-anthracene tetracarboxylic dianhydride, 1,2,7,8-phenanthrene tetracarboxylic dianhydride, etc. are mentioned. These may be used alone or in combination of two or more. Among these, it is particularly preferable to use pyromellitic dianhydride as at least one of the components.
芳香族多価カルボン酸無水物等の多価カルボン酸と反応させる芳香族ジアミンの具体例としては、例えば、m−フェニレンジアミン、o−フェニレンジアミン、p−フェニレンジアミン、m−アミノベンジルアミン、p−アミノベンジルアミン、4,4’−ジアミノジフェニルエーテル、3,3’−ジアミノジフェニルエーテル、3,4’−ジアミノジフェニルエーテル、ビス(3−アミノフェニル)スルフィド、(3−アミノフェニル)(4−アミノフェニル)スルフィド、ビス(4−アミノフェニル)スルフィド、ビス(3−アミノフェニル)スルフィド、(3−アミノフェニル)(4−アミノフェニル)スルホキシド、ビス(3−アミノフェニル)スルホン、(3−アミノフェニル)(4−アミノフェニル)スルホン、ビス(4−アミノフェニル)スルホン、3,3’−ジアミノベンゾフェノン、3,4’−ジアミノベンゾフェノン、4,4’−ジアミノベンゾフェノン、3,3’−ジアミノジフェニルメタン、3,4’−ジアミノジフェニルメタン、4,4’−ジアミノジフェニルメタン、ビス〔4−(3−アミノフェノキシ)フェニル〕メタン、ビス〔4−(4−アミノフェノキシ)フェニル〕メタン、1,1−ビス〔4−(3−アミノフェノキシ)フェニル〕エタン、1,1−ビス〔4−(4−アミノフェノキシ)フェニル〕−エタン、1,2−ビス〔4−(3−アミノフェノキシ)フェニル〕エタン、1,2−ビス〔4−(4−アミノフェノキシ)フェニル〕エタン、2,2−ビス〔4−(3−アミノフェノキシ)フェニル〕プロパン、2,2−ビス〔4−(4−アミノフェノキシ)フェニル〕プロパン、2,2−ビス〔4−(3−アミノフェノキシ)フェニル〕ブタン、2,2−ビス〔3−(3−アミノフェノキシ)フェニル〕−1,1,1,3,3,3−ヘキサフルオロプロパン、2,2−ビス〔4−(4−アミノフェノキシ)フェニル〕−1,1,1,3,3,3−ヘキサフルオロプロパン、1,3−ビス(3−アミノフェノキシ)ベンゼン、1,3−ビス(4−アミノフェノキシ)ベンゼン、1,4−ビス(3−アミノフェノキシ)ベンゼン、1,4−ビス(4−アミノフェノキシ)ベンゼン、4,4’−ビス(3−アミノフェノキシ)ビフェニル、4,4’−ビス(4−アミノフェノキシ)ビフェニル、ビス〔4−(3−アミノフェノキシ)フェニル〕ケトン、ビス〔4−(4−アミノフェノキシ)フェニル〕ケトン、ビス〔4−(3−アミノフェノキシ)フェニル〕スルフィド、ビス〔4−(4−アミノフェノキシ)フェニル〕スルフィド、ビス〔4−(3−アミノフェノキシ)フェニル〕スルホキシド、ビス〔4−(4−アミノフェノキシ)フェニル〕スルホキシド、ビス〔4−(3−アミノフェノキシ)フェニル〕スルホン、ビス〔4−(4−アミノフェノキシ)フェニル〕スルホン、ビス〔4−(3−アミノフェノキシ)フェニル〕エーテル、ビス〔4−(4−アミノフェノキシ)フェニル〕エーテル、1,4−ビス〔4−(3−アミノフェノキシ)ベンゾイル〕ベンゼン、1,3−ビス〔4−(3−アミノフェノキシ)ベンゾイル〕ベンゼン、4,4’−ビス〔3−(4−アミノフェノキシ)ベンゾイル〕ジフェニルエーテル、4,4’−ビス〔3−(3−アミノフェノキシ)ベンゾイル〕ジフェニルエーテル、4,4’−ビス〔4−(4−アミノ−α,α−ジメチルベンジル)フェノキシ〕ベンゾフェノン、4,4’−ビス〔4−(4−アミノ−α,α−ジメチルベンジル)フェノキシ〕ジフェニルスルホン、ビス〔4−{4−(4−アミノフェノキシ)フェノキシ}フェニル〕スルホン、1,4−ビス〔4−(4−アミノフェノキシ)フェノキシ〕−α,α−ジメチルベンジル〕ベンゼン、1,3−ビス〔4−(4−アミノフェノキシ)−α,α−ジメチルベンジル〕ベンゼン等が挙げられる。これらは単独または2種以上を混合して使用される。これらの中でも、特に、少なくとも成分の1つとして、4,4’−ジアミノジフェニルエーテルを用いることが好ましい。 Specific examples of the aromatic diamine to be reacted with a polyvalent carboxylic acid such as an aromatic polyvalent carboxylic acid anhydride include, for example, m-phenylenediamine, o-phenylenediamine, p-phenylenediamine, m-aminobenzylamine, p. -Aminobenzylamine, 4,4'-diaminodiphenyl ether, 3,3'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, bis (3-aminophenyl) sulfide, (3-aminophenyl) (4-aminophenyl) Sulfide, bis (4-aminophenyl) sulfide, bis (3-aminophenyl) sulfide, (3-aminophenyl) (4-aminophenyl) sulfoxide, bis (3-aminophenyl) sulfone, (3-aminophenyl) ( 4-aminophenyl) sulfone, bis (4-ami) Phenyl) sulfone, 3,3'-diaminobenzophenone, 3,4'-diaminobenzophenone, 4,4'-diaminobenzophenone, 3,3'-diaminodiphenylmethane, 3,4'-diaminodiphenylmethane, 4,4'-diamino Diphenylmethane, bis [4- (3-aminophenoxy) phenyl] methane, bis [4- (4-aminophenoxy) phenyl] methane, 1,1-bis [4- (3-aminophenoxy) phenyl] ethane, 1, 1-bis [4- (4-aminophenoxy) phenyl] -ethane, 1,2-bis [4- (3-aminophenoxy) phenyl] ethane, 1,2-bis [4- (4-aminophenoxy) phenyl ] Ethane, 2,2-bis [4- (3-aminophenoxy) phenyl] propane, 2,2-bis [4- (4-a Nophenoxy) phenyl] propane, 2,2-bis [4- (3-aminophenoxy) phenyl] butane, 2,2-bis [3- (3-aminophenoxy) phenyl] -1,1,1,3,3 3,3-hexafluoropropane, 2,2-bis [4- (4-aminophenoxy) phenyl] -1,1,1,3,3,3-hexafluoropropane, 1,3-bis (3-amino Phenoxy) benzene, 1,3-bis (4-aminophenoxy) benzene, 1,4-bis (3-aminophenoxy) benzene, 1,4-bis (4-aminophenoxy) benzene, 4,4'-bis ( 3-aminophenoxy) biphenyl, 4,4'-bis (4-aminophenoxy) biphenyl, bis [4- (3-aminophenoxy) phenyl] ketone, bis [4- (4-aminophenoxy) ) Phenyl] ketone, bis [4- (3-aminophenoxy) phenyl] sulfide, bis [4- (4-aminophenoxy) phenyl] sulfide, bis [4- (3-aminophenoxy) phenyl] sulfoxide, bis [4 -(4-Aminophenoxy) phenyl] sulfoxide, bis [4- (3-aminophenoxy) phenyl] sulfone, bis [4- (4-aminophenoxy) phenyl] sulfone, bis [4- (3-aminophenoxy) phenyl ] Ether, bis [4- (4-aminophenoxy) phenyl] ether, 1,4-bis [4- (3-aminophenoxy) benzoyl] benzene, 1,3-bis [4- (3-aminophenoxy) benzoyl ] Benzene, 4,4'-bis [3- (4-aminophenoxy) benzoyl] diphenyl ether 4,4′-bis [3- (3-aminophenoxy) benzoyl] diphenyl ether, 4,4′-bis [4- (4-amino-α, α-dimethylbenzyl) phenoxy] benzophenone, 4,4′-bis [4- (4-amino-α, α-dimethylbenzyl) phenoxy] diphenyl sulfone, bis [4- {4- (4-aminophenoxy) phenoxy} phenyl] sulfone, 1,4-bis [4- (4- Aminophenoxy) phenoxy] -α, α-dimethylbenzyl] benzene, 1,3-bis [4- (4-aminophenoxy) -α, α-dimethylbenzyl] benzene and the like can be mentioned. These may be used alone or in admixture of two or more. Among these, 4,4'-diaminodiphenyl ether is particularly preferably used as at least one of the components.
ポリイミドワニスとしては、新日本理化(株)製のリカコートSN20、リカコートPN20、リカコートEN20、東レ(株)製のトレニース、宇部興産(株)製U−ワニス、JSR(株)製のオプトマー、日産化学(株)製のSE812、住友ベークライト(株)製のCRC8000が挙げられる。 As the polyimide varnish, Rika Coat SN20, Rica Coat PN20, Rica Coat EN20, Toray Co., Ltd., Treney, Ube Kosan Co., Ltd. U-varnish, JSR Co., Ltd. Optomer, Nissan Kagaku Co., Ltd. are available. Examples include SE812 manufactured by Co., Ltd. and CRC8000 manufactured by Sumitomo Bakelite Co., Ltd.
合成反応により得られるかまたは上市されているポリアミック酸溶液を、加熱等により処理することで、ポリアミック酸からポリイミドへの環化(イミド化)が行なわれる。ポリアミック酸は、加熱のみによる方法、または、化学的方法によって、イミド化することが可能である。加熱のみによる方法の場合、ポリアミック酸を、例えば、200〜350℃で加熱処理することによってイミド化する。また、化学的方法は、イミド化を速やかに進行させるために塩基性触媒を利用しつつ、ポリアミック酸を加熱処理して、完全にイミド化する方法である。上記塩基性触媒としては、特に限定されず、従来公知の塩基性触媒が用いられ、例えば、ピリジン、ジアザビシクロウンデセン(DBU)、ジアザビシクロノネン(DBN)、各種3級アミン等が挙げられる。これらの塩基性触媒は、単独で用いてもよいし、二種類以上を併用してもよい。 The polyamic acid solution obtained by the synthetic reaction or put on the market is treated by heating or the like to cyclize the polyamic acid to a polyimide (imidization). The polyamic acid can be imidized by a method involving only heating or a chemical method. In the case of the method of only heating, the polyamic acid is imidized by heating at 200 to 350 ° C., for example. In addition, the chemical method is a method in which a polyamic acid is heat-treated and completely imidized while using a basic catalyst in order to promptly promote imidization. The basic catalyst is not particularly limited, and a conventionally known basic catalyst is used, and examples thereof include pyridine, diazabicycloundecene (DBU), diazabicyclononene (DBN), and various tertiary amines. To be These basic catalysts may be used alone or in combination of two or more.
(光硬化性樹脂)
光硬化性樹脂としては、活性エネルギー線の照射により硬化して電気絶縁性を示す樹脂であればよく、特には、分子中に1個以上のエチレン性不飽和結合を有する化合物が好ましく用いられる。エチレン性不飽和結合を有する化合物としては、公知慣用の光重合性オリゴマーおよび光重合性ビニルモノマー等が用いられる。(Photocurable resin)
The photocurable resin may be a resin that is cured by irradiation with active energy rays and exhibits electrical insulation properties. In particular, a compound having one or more ethylenically unsaturated bonds in the molecule is preferably used. As the compound having an ethylenically unsaturated bond, known and commonly used photopolymerizable oligomers and photopolymerizable vinyl monomers are used.
光重合性オリゴマーとしては、不飽和ポリエステル系オリゴマー、(メタ)アクリレート系オリゴマー等が挙げられる。(メタ)アクリレート系オリゴマーとしては、フェノールノボラックエポキシ(メタ)アクリレート、クレゾールノボラックエポキシ(メタ)アクリレート、ビスフェノール型エポキシ(メタ)アクリレート等のエポキシ(メタ)アクリレート、ウレタン(メタ)アクリレート、エポキシウレタン(メタ)アクリレート、ポリエステル(メタ)アクリレート、ポリエーテル(メタ)アクリレート、ポリブタジエン変性(メタ)アクリレート等が挙げられる。なお、本明細書において、(メタ)アクリレートとは、アクリレート、メタクリレートおよびそれらの混合物を総称する用語であり、他の類似の表現についても同様である。 Examples of the photopolymerizable oligomer include unsaturated polyester-based oligomers and (meth) acrylate-based oligomers. Examples of (meth) acrylate-based oligomers include epoxy (meth) acrylates such as phenol novolac epoxy (meth) acrylate, cresol novolac epoxy (meth) acrylate, and bisphenol type epoxy (meth) acrylate, urethane (meth) acrylate, and epoxy urethane (meth). ) Acrylate, polyester (meth) acrylate, polyether (meth) acrylate, polybutadiene modified (meth) acrylate and the like. In addition, in this specification, (meth) acrylate is a general term for acrylate, methacrylate, and a mixture thereof, and the same applies to other similar expressions.
光重合性ビニルモノマーとしては、公知慣用のもの、例えば、スチレン、クロロスチレン、α−メチルスチレンなどのスチレン誘導体;酢酸ビニル、酪酸ビニルまたは安息香酸ビニルなどのビニルエステル類;ビニルイソブチルエーテル、ビニル−n−ブチルエーテル、ビニル−t−ブチルエーテル、ビニル−n−アミルエーテル、ビニルイソアミルエーテル、ビニル−n−オクタデシルエーテル、ビニルシクロヘキシルエーテル、エチレングリコールモノブチルビニルエーテル、トリエチレングリコールモノメチルビニルエーテルなどのビニルエーテル類;アクリルアミド、メタクリルアミド、N−ヒドロキシメチルアクリルアミド、N−ヒドロキシメチルメタクリルアミド、N−メトキシメチルアクリルアミド、N−エトキシメチルアクリルアミド、N−ブトキシメチルアクリルアミドなどの(メタ)アクリルアミド類;トリアリルイソシアヌレート、フタル酸ジアリル、イソフタル酸ジアリルなどのアリル化合物;2−エチルヘキシル(メタ)アクリレート、ラウリル(メタ)アクリレート、テトラヒドロフルフリール(メタ)アクリレート、イソボロニル(メタ)アクリレート、フェニル(メタ)アクリレート、フェノキシエチル(メタ)アクリレートなどの(メタ)アクリル酸のエステル類;ヒドロキシエチル(メタ)アクリレート、ヒドロキシプロピル(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレートなどのヒドロキシアルキル(メタ)アクリレート類;メトキシエチル(メタ)アクリレート、エトキシエチル(メタ)アクリレートなどのアルコキシアルキレングリコールモノ(メタ)アクリレート類;エチレングリコールジ(メタ)アクリレート、ブタンジオールジ(メタ)アクリレート類、ネオペンチルグリコールジ(メタ)アクリレート、1,6−ヘキサンジオールジ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレートなどのアルキレンポリオールポリ(メタ)アクリレート、;ジエチレングリコールジ(メタ)アクリレート、トリエチレングリコールジ(メタ)アクリレート、エトキシ化トリメチロールプロパントリアクリレート、プロポキシ化トリメチロールプロパントリ(メタ)アクリレートなどのポリオキシアルキレングリコールポリ(メタ)アクリレート類;ヒドロキシビバリン酸ネオペンチルグリコールエステルジ(メタ)アクリレートなどのポリ(メタ)アクリレート類;トリス[(メタ)アクリロキシエチル]イソシアヌレートなどのイソシアヌルレート型ポリ(メタ)アクリレート類などが挙げられる。 As the photopolymerizable vinyl monomer, known conventional ones, for example, styrene derivatives such as styrene, chlorostyrene, α-methylstyrene; vinyl esters such as vinyl acetate, vinyl butyrate or vinyl benzoate; vinyl isobutyl ether, vinyl- Vinyl ethers such as n-butyl ether, vinyl-t-butyl ether, vinyl-n-amyl ether, vinyl isoamyl ether, vinyl-n-octadecyl ether, vinyl cyclohexyl ether, ethylene glycol monobutyl vinyl ether, triethylene glycol monomethyl vinyl ether; acrylamide, Methacrylamide, N-hydroxymethyl acrylamide, N-hydroxymethyl methacrylamide, N-methoxymethyl acrylamide, N-ethoxymethyl acrylamide (Meth) acrylamides such as luamide and N-butoxymethylacrylamide; allyl compounds such as triallyl isocyanurate, diallyl phthalate and diallyl isophthalate; 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, tetrahydrofurfuryl Esters of (meth) acrylic acid such as (meth) acrylate, isobornyl (meth) acrylate, phenyl (meth) acrylate, phenoxyethyl (meth) acrylate; hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, pentaerythritol Hydroxyalkyl (meth) acrylates such as tri (meth) acrylate; Alcohols such as methoxyethyl (meth) acrylate and ethoxyethyl (meth) acrylate Xyalkylene glycol mono (meth) acrylates; ethylene glycol di (meth) acrylate, butanediol di (meth) acrylates, neopentyl glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, trimethylol Propylene tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate and other alkylene polyol poly (meth) acrylates; diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, Ethoxylated trimethylolpropane triacrylate, propoxylated trimethylolpropane tri (meth) acrylate and other polyoxyalkylene glycol poly ( A) acrylates; poly (meth) acrylates such as hydroxybivalic acid neopentyl glycol ester di (meth) acrylates; isocyanurate type poly (meth) acrylates such as tris [(meth) acryloxyethyl] isocyanurate Is mentioned.
光硬化性樹脂としては、脂環エポキシ化合物、オキセタン化合物およびビニルエーテル化合物等も好適に用いることができる。このうち脂環エポキシ化合物としては、3,4,3’,4’−ジエポキシビシクロヘキシル、2,2−ビス(3,4−エポキシシクロヘキシル)プロパン、2,2−ビス(3,4−エポキシシクロヘキシル)−1,3−ヘキサフルオロプロパン、ビス(3,4−エポキシシクロヘキシル)メタン、1−[1,1−ビス(3,4−エポキシシクロヘキシル)]エチルベンゼン、ビス(3,4−エポキシシクロヘキシル)アジペート、3,4−エポキシシクロヘキシルメチル(3,4−エポキシ)シクロヘキサンカルボキシレート、(3,4−エポキシ−6−メチルシクロヘキシル)メチル−3’,4’−エポキシ−6−メチルシクロヘキサンカルボキシレート、エチレン−1,2−ビス(3,4−エポキシシクロヘキサンカルボン酸)エステル、シクロヘキセンオキサイド、3,4−エポキシシクロヘキシルメチルアルコール、3,4−エポキシシクロヘキシルエチルトリメトキシシラン等のエポキシ基を有する脂環エポキシ化合物などが挙げられる。 As the photocurable resin, an alicyclic epoxy compound, an oxetane compound, a vinyl ether compound or the like can also be preferably used. Of these, alicyclic epoxy compounds include 3,4,3 ', 4'-diepoxybicyclohexyl, 2,2-bis (3,4-epoxycyclohexyl) propane, 2,2-bis (3,4-epoxy) Cyclohexyl) -1,3-hexafluoropropane, bis (3,4-epoxycyclohexyl) methane, 1- [1,1-bis (3,4-epoxycyclohexyl)] ethylbenzene, bis (3,4-epoxycyclohexyl) Adipate, 3,4-epoxycyclohexylmethyl (3,4-epoxy) cyclohexanecarboxylate, (3,4-epoxy-6-methylcyclohexyl) methyl-3 ', 4'-epoxy-6-methylcyclohexanecarboxylate, ethylene -1,2-bis (3,4-epoxycyclohexanecarboxylic acid) ester Cyclohexene oxide, 3,4-epoxycyclohexylmethyl alcohol and alicyclic epoxy compounds having an epoxy group such as 3,4-epoxycyclohexyl ethyl trimethoxy silane.
オキセタン化合物としては、ビス[(3−メチル−3−オキセタニルメトキシ)メチル]エーテル、ビス[(3−エチル−3−オキセタニルメトキシ)メチル]エーテル、1,4−ビス[(3−メチル−3−オキセタニルメトキシ)メチル]ベンゼン、1,4−ビス[(3−エチル−3−オキセタニルメトキシ)メチル]ベンゼン、(3−メチル−3−オキセタニル)メチルアクリレート、(3−エチル−3−オキセタニル)メチルアクリレート、(3−メチル−3−オキセタニル)メチルメタクリレート、(3−エチル−3−オキセタニル)メチルメタクリレートやそれらのオリゴマーまたは共重合体などの多官能オキセタン類の他、オキセタンアルコールとノボラック樹脂、ポリ(p−ヒドロキシスチレン)、カルド型ビスフェノール類、カリックスアレーン類、カリックスレゾルシンアレーン類、またはシルセスキオキサンなどの水酸基を有する樹脂とのエーテル化物、オキセタン環を有する不飽和モノマーとアルキル(メタ)アクリレートとの共重合体等のオキセタン化合物が挙げられる。 As the oxetane compound, bis [(3-methyl-3-oxetanylmethoxy) methyl] ether, bis [(3-ethyl-3-oxetanylmethoxy) methyl] ether, 1,4-bis [(3-methyl-3-) Oxetanylmethoxy) methyl] benzene, 1,4-bis [(3-ethyl-3-oxetanylmethoxy) methyl] benzene, (3-methyl-3-oxetanyl) methyl acrylate, (3-ethyl-3-oxetanyl) methyl acrylate , (3-methyl-3-oxetanyl) methyl methacrylate, (3-ethyl-3-oxetanyl) methyl methacrylate, and polyfunctional oxetanes such as oligomers or copolymers thereof, oxetane alcohol and novolac resin, poly (p -Hydroxystyrene), cardo type bisphenols Examples include oxetane compounds such as calixarenes, calixresorcinarenes, and etherification products with resins having a hydroxyl group such as silsesquioxane, and copolymers of unsaturated monomers having an oxetane ring and alkyl (meth) acrylates. .
ビニルエーテル化合物としては、イソソルバイトジビニルエーテル、オキサノルボルネンジビニルエーテル等の環状エーテル型ビニルエーテル(オキシラン環、オキセタン環、オキソラン環等の環状エーテル基を有するビニルエーテル);フェニルビニルエーテル等のアリールビニルエーテル;n−ブチルビニルエーテル、オクチルビニルエーテル等のアルキルビニルエーテル;シクロヘキシルビニルエーテル等のシクロアルキルビニルエーテル;ハイドロキノンジビニルエーテル、1,4−ブタンジオールジビニルエーテル、シクロヘキサンジビニルエーテル、シクロヘキサンジメタノールジビニルエーテル等の多官能ビニルエーテル、αおよび/またはβ位にアルキル基、アリル基等の置換基を有するビニルエーテル化合物などが挙げられる。市販品としては、例えば、丸善石油化学(株)製の2−ヒドロキシエチルビニルエーテル(HEVE)、ジエチレングリコールモノビニルエーテル(DEGV)、2−ヒドロキシブチルビニルエーテル(HBVE)、トリエチレングリコールジビニルエーテルなどが挙げられる。 Examples of vinyl ether compounds include cyclic ether type vinyl ethers such as isosorbite divinyl ether and oxanorbornene divinyl ether (vinyl ethers having a cyclic ether group such as oxirane ring, oxetane ring and oxolane ring); aryl vinyl ethers such as phenyl vinyl ether; n-butyl vinyl ether , Alkyl vinyl ethers such as octyl vinyl ether; cycloalkyl vinyl ethers such as cyclohexyl vinyl ether; polyfunctional vinyl ethers such as hydroquinone divinyl ether, 1,4-butanediol divinyl ether, cyclohexane divinyl ether, cyclohexane dimethanol divinyl ether, α and / or β position Include vinyl ether compounds having a substituent such as an alkyl group and an allyl group. It Examples of commercially available products include 2-hydroxyethyl vinyl ether (HEVE), diethylene glycol monovinyl ether (DEGV), 2-hydroxybutyl vinyl ether (HBVE), and triethylene glycol divinyl ether manufactured by Maruzen Petrochemical Co., Ltd.
光硬化性樹脂を用いる場合には、上述した光硬化性樹脂に加えて、光重合開始剤、光酸発生剤、光塩基発生剤等が用いられ、これらのうちの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。 When a photocurable resin is used, a photopolymerization initiator, a photoacid generator, a photobase generator, etc. are used in addition to the above-mentioned photocurable resin, and one of these is used alone or Two or more kinds can be used in combination.
光重合開始剤としては、例えば、ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル等のベンゾインとベンゾインアルキルエーテル類;アセトフェノン、2,2−ジメトキシ−2−フェニルアセトフェノン、2,2−ジエトキシ−2−フェニルアセトフェノン、2,2−ジエトキシ−2−フェニルアセトフェノン、1,1−ジクロロアセトフェノン等のアセトフェノン類;2−メチル−1−[4−(メチルチオ)フェニル]−2−モルフォリノプロパン−1−オン、2−ベンジル−2−ジメチルアミノ−1−(4−モルフォリノフェニル)−ブタノン−1、2−(ジメチルアミノ)−2−[(4−メチルフェニル)メチル]−1−[4−(4−モルフォリニル)フェニル]−1−ブタノン等のアミノアルキルフェノン類;2−メチルアントラキノン、2−エチルアントラキノン、2−ターシャリーブチルアントラキノン、1−クロロアントラキノン等のアントラキノン類;2,4−ジメチルチオキサントン、2,4−ジエチルチオキサントン、2−クロロチオキサントン、2,4−ジイソプロピルチオキサントン等のチオキサントン類;アセトフェノンジメチルケタール、ベンジルジメチルケタール等のケタール類;ベンゾフェノン等のベンゾフェノン類;またはキサントン類;(2,6−ジメトキシベンゾイル)−2,4,4−ペンチルホスフィンオキサイド、ビス(2,4,6−トリメチルベンゾイル)−フェニルフォスフィンオキサイド、2,4,6−トリメチルベンゾイルジフェニルフォスフィンオキサイド、エチル−2,4,6−トリメチルベンゾイルフェニルフォスフィネイト等のフォスフィンオキサイド類;各種パーオキサイド類、チタノセン系開始剤、オキシムエステル系開始剤などが挙げられる。これらは、N,N−ジメチルアミノ安息香酸エチルエステル、N,N−ジメチルアミノ安息香酸イソアミルエステル、ペンチル−4−ジメチルアミノベンゾエート、トリエチルアミン、トリエタノールアミン等の三級アミン類のような光増感剤等と併用してもよい。これらの光重合開始剤は単独で、または2種以上を組み合わせて用いることができる。 Examples of the photopolymerization initiator include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and other benzoin and benzoin alkyl ethers; acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy- Acetophenones such as 2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone and 1,1-dichloroacetophenone; 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1- On, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1,2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- ( 4-morpholinyl) phenyl] -1-butanone Aminoalkylphenones; 2-methylanthraquinone, 2-ethylanthraquinone, 2-tert-butylanthraquinone, 1-chloroanthraquinone and other anthraquinones; 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone , 2,4-diisopropylthioxanthone and other thioxanthones; acetophenone dimethyl ketal, benzyl dimethyl ketal and other ketals; benzophenone and other benzophenones; or xanthones; (2,6-dimethoxybenzoyl) -2,4,4-pentyl Phosphine oxide, bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, ethyl- , 4,6-phosphine oxide such as trimethyl benzoyl phenyl phosphinothricin Nate; various peroxides, titanocene initiators, and the like oxime ester initiator. These are photosensitizers such as tertiary amines such as N, N-dimethylaminobenzoic acid ethyl ester, N, N-dimethylaminobenzoic acid isoamyl ester, pentyl-4-dimethylaminobenzoate, triethylamine and triethanolamine. You may use together with agents. These photopolymerization initiators can be used alone or in combination of two or more kinds.
光酸発生剤としては、例えば、ジアゾニウム塩、ヨードニウム塩、ブロモニウム塩、クロロニウム塩、スルホニウム塩、セレノニウム塩、ピリリウム塩、チアピリリウム塩、ピリジニウム塩等のオニウム塩;トリス(トリハロメチル)−s−トリアジン(例えば、2,4,6−トリス(トリクロロメチル)−s−トリアジン)、2−[2−(5−メチルフラン−2−イル)エテニル]−4,6−ビス(トリクロロメチル)−s−トリアジン、2−[2−(フラン−2−イル)エテニル]−4,6−ビス(トリクロロメチル)−s−トリアジン、2−(4−メトキシフェニル)−4,6−ビス(トリクロロメチル)−s−トリアジン、2−メチル−4,6−ビス(トリクロロメチル)−s−トリアジン等のハロゲン化化合物;スルホン酸の2−ニトロベンジルエステル;イミノスルホナート;1−オキソ−2−ジアゾナフトキノン−4−スルホナート誘導体;N−ヒドロキシイミド=スルホナート;トリ(メタンスルホニルオキシ)ベンゼン誘導体;ビススルホニルジアゾメタン類;スルホニルカルボニルアルカン類;スルホニルカルボニルジアゾメタン類;ジスルホン化合物;鉄アレン錯体等を挙げることができる。これらの光酸発生剤は、単独で、または2種類以上組み合わせて用いることができる。 Examples of the photoacid generator include onium salts such as diazonium salts, iodonium salts, bromonium salts, chloronium salts, sulfonium salts, selenonium salts, pyrylium salts, thiapyrylium salts, and pyridinium salts; tris (trihalomethyl) -s-triazine ( For example, 2,4,6-tris (trichloromethyl) -s-triazine), 2- [2- (5-methylfuran-2-yl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine , 2- [2- (furan-2-yl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxyphenyl) -4,6-bis (trichloromethyl) -s. -Halogenated compounds such as triazine and 2-methyl-4,6-bis (trichloromethyl) -s-triazine; sulfonic acid 2- Trobenzyl ester; iminosulfonate; 1-oxo-2-diazonaphthoquinone-4-sulfonate derivative; N-hydroxyimide = sulfonate; tri (methanesulfonyloxy) benzene derivative; bissulfonyldiazomethanes; sulfonylcarbonylalkanes; sulfonylcarbonyl Examples thereof include diazomethanes, disulfone compounds, iron allene complexes and the like. These photo-acid generators can be used alone or in combination of two or more kinds.
光塩基発生剤は、紫外線や可視光等の光照射により分子構造が変化するか、または、分子が開裂することにより、重合反応の触媒として機能しうる1種以上の塩基性物質を生成する化合物である。塩基性物質として、例えば2級アミン、3級アミンが挙げられる。このような光塩基発生剤としては、例えば、α−アミノアセトフェノン化合物や、オキシムエステル化合物、アシルオキシイミノ基,N−ホルミル化芳香族アミノ基、N−アシル化芳香族アミノ基、ニトロベンジルカーバメイト基、アルコオキシベンジルカーバメート基等の置換基を有する化合物等が挙げられる。これらの光塩基発生剤は、単独で、または2種類以上組み合わせて用いることができる。 The photobase generator is a compound that produces one or more basic substances capable of functioning as a catalyst for a polymerization reaction by changing the molecular structure or cleaving the molecule by irradiation with light such as ultraviolet rays or visible light. Is. Examples of the basic substance include secondary amine and tertiary amine. Examples of such photobase generators include α-aminoacetophenone compounds, oxime ester compounds, acyloxyimino groups, N-formylated aromatic amino groups, N-acylated aromatic amino groups, and nitrobenzylcarbamate groups. Examples thereof include compounds having a substituent such as alcooxybenzyl carbamate group. These photobase generators can be used alone or in combination of two or more kinds.
有機溶媒としては、アセトン、メチルエチルケトン、シクロヘキサノンなどのケトン類;トルエン、キシレン、テトラメチルベンゼンなどの芳香族炭化水素類;メチルセロソルブ、エチルセロソルブ、ブチルセロソルブ、メチルカルビトール、ブチルカルビトール、プロピレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジプロプ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エチルエーテルなどのグリコールエーテル類;酢酸エチル、酢酸ブチル、セロソルブアセテート、ジエチレングリコールモノエチルエーテルアセテートおよび上記グリコールエーテル類のエステル化物などのエステル類;エタノール、プロパノール、エチレングリコール、プロピレングリコールなどのアルコール類;1−メチル−2−ピロリジノン、1,3−ジメチル−2−イミダゾリジノン、2−ピロリジノン、ε−カプロラクタム、ホルムアミド、N−メチルホルムアミド、N,N−ジメチルホルムアミド、アセトアミド、N−メチルアセトアミド等のアミド類;テトラヒドロフラン、ジオキサンなどのエーテル類;アセトニトリル、ベンゾニトリル、プロピオニトリル等のニトリル類、クロロホルム、ジクロロメタン、ブロモベンゼン、ジブロモベンゼン、クロロベンゼン、ジクロロベンゼン等のハロゲン類;N−メチル−2−ピロリドン、ジメチルアニリン、ジブチルアニリン、ジイソプロピルアニリン等のアミン類;ジメチルスルホキシド、スルホラン等の含硫黄類;オクタン、デカンなどの脂肪族炭化水素類;石油エーテル、石油ナフサ、水添石油ナフサ、ソルベントナフサなどの石油系溶媒等を挙げることができる。これらの中でも、N−メチル−2−ピロリドンやメチルエチルケトンは、取扱いが容易であるため好ましい。 Examples of the organic solvent include ketones such as acetone, methyl ethyl ketone and cyclohexanone; aromatic hydrocarbons such as toluene, xylene and tetramethylbenzene; methyl cellosolve, ethyl cellosolve, butyl cellosolve, methyl carbitol, butyl carbitol, propylene glycol monomethyl ether. Glycol ethers such as diethylene glycol monoethyl ether, dipropylene glycol monoethyl ether and triethylene glycol monoethyl ether; esters such as ethyl acetate, butyl acetate, cellosolve acetate, diethylene glycol monoethyl ether acetate and esterification products of the above glycol ethers Kinds; alcohols such as ethanol, propanol, ethylene glycol, propylene glycol 1-methyl-2-pyrrolidinone, 1,3-dimethyl-2-imidazolidinone, 2-pyrrolidinone, ε-caprolactam, formamide, N-methylformamide, N, N-dimethylformamide, acetamide, N-methylacetamide, etc. Amides; tetrahydrofuran, dioxane, and other ethers; acetonitrile, benzonitrile, propionitrile, and other nitriles, chloroform, dichloromethane, bromobenzene, dibromobenzene, chlorobenzene, dichlorobenzene, and other halogens, N-methyl-2- Amines such as pyrrolidone, dimethylaniline, dibutylaniline, diisopropylaniline; sulfur-containing compounds such as dimethyl sulfoxide and sulfolane; aliphatic hydrocarbons such as octane and decane; petroleum ether, petroleum naphtha, water Examples thereof include petroleum-based solvents such as added petroleum naphtha and solvent naphtha. Among these, N-methyl-2-pyrrolidone and methyl ethyl ketone are preferable because they are easy to handle.
[樹脂組成物]
本発明の樹脂含有シートにおいて、樹脂3は、固着剤2と繊維基材11とに接するものである。本発明において、樹脂3は、密着性を確保する役割を奏しうるものであればよいので、繊維基材11の外側を被覆していてもよい。樹脂組成物の含浸率としては、樹脂含有シートを金属箔等に密着することができるものであれば特に限定はないが、樹脂含有シート中の樹脂の濃度として、10〜99体積%、特には、10〜70体積%であることが好ましい。樹脂組成物の含浸率を上記範囲内とすることで、良好な密着性と、高強度とをバランス良く得ることができる。[Resin composition]
In the resin-containing sheet of the present invention, the resin 3 is in contact with the adhesive 2 and the
樹脂3を形成する樹脂組成物としては、熱硬化性樹脂、光硬化性樹脂および熱可塑性樹脂のうちから選ばれる少なくとも1種類を含むものとすることができ、その用途に応じて、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。中でも、硬化物または成形物の物性の観点から、熱硬化性樹脂が好ましく、エポキシ樹脂を用いることがさらに好ましい。樹脂組成物として、熱硬化性樹脂ないし光硬化性樹脂を使用する場合には、固着剤組成物について挙げたのと同様の熱硬化性樹脂、光硬化性樹脂、有機溶媒等を適宜使用することが可能であり、本発明においては、樹脂組成物および固着剤組成物が、それぞれ異なればよい。また、熱可塑性樹脂としては、以下に示すものが使用可能である。 The resin composition that forms the resin 3 may include at least one selected from thermosetting resins, photocurable resins, and thermoplastic resins, and one type may be used alone depending on the application. Or, two or more kinds can be used in combination. Of these, thermosetting resins are preferable, and epoxy resins are more preferable, from the viewpoint of the physical properties of the cured product or molded product. When a thermosetting resin or a photocurable resin is used as the resin composition, the same thermosetting resin, photocurable resin, organic solvent, etc. as those mentioned for the adhesive composition should be used appropriately. In the present invention, the resin composition and the adhesive composition may be different from each other. Further, as the thermoplastic resin, the following ones can be used.
(熱可塑性樹脂)
熱可塑性樹脂としては、アクリル、変性アクリル、低密度ポリエチレン、高密度ポリエチレン、エチレン−酢酸ビニル共重合体、ポリエチレンテレフタレート、ポリプロピレン、変性ポリプロピレン、ポリスチレン、アクリロニトリル−ブタジエン−スチレン共重合体、アクリロニトリル−スチレン共重合体、酢酸セルロース、ポリビニルアルコール、ポリ塩化ビニル、ポリ塩化ビニリデン、ポリ乳酸等の汎用プラスチック類、ポリアミド、熱可塑性ポリウレタン、ポリアセタール、ポリカーボネート、超高分子量ポリエチレン、ポリブチレンテレフタレート、変性ポリフェニレンエーテル、ポリスルホン(PSF)、ポリフェニレンスルファイド(PPS)、ポリエーテルスルホン(PES)、ポリエーテルエーテルケトン、ポリアリレート、ポリエーテルイミド、ポリアミドイミド、液晶ポリマー、ポリアミド6T、ポリアミド9T、ポリテトラフロロエチレン、ポリフッ化ビニリデン、ポリエステルイミド、熱可塑性ポリイミド等のエンジニアリングプラスチック類、オレフィン系、スチレン系、ポリエステル系、ウレタン系、アミド系、塩化ビニル系、水添系等の熱可塑性エラストマーが挙げられる。本発明においては、樹脂複合体を使用することもでき、例えば、熱硬化性樹脂と熱可塑性樹脂の樹脂複合体として、エポキシ樹脂−PSF、エポキシ樹脂−PPS、エポキシ樹脂−PES等が使用できる。(Thermoplastic resin)
Examples of the thermoplastic resin include acrylic, modified acrylic, low-density polyethylene, high-density polyethylene, ethylene-vinyl acetate copolymer, polyethylene terephthalate, polypropylene, modified polypropylene, polystyrene, acrylonitrile-butadiene-styrene copolymer, acrylonitrile-styrene copolymer. Polymers, cellulose acetate, polyvinyl alcohol, polyvinyl chloride, polyvinylidene chloride, polylactic acid and other general-purpose plastics, polyamide, thermoplastic polyurethane, polyacetal, polycarbonate, ultra high molecular weight polyethylene, polybutylene terephthalate, modified polyphenylene ether, polysulfone ( PSF), polyphenylene sulfide (PPS), polyethersulfone (PES), polyetheretherketone, polyalley , Engineering plastics such as polyetherimide, polyamideimide, liquid crystal polymer, polyamide 6T, polyamide 9T, polytetrafluoroethylene, polyvinylidene fluoride, polyesterimide, thermoplastic polyimide, olefin series, styrene series, polyester series, urethane series, Examples thereof include amide type, vinyl chloride type and hydrogenated type thermoplastic elastomers. In the present invention, a resin composite can be used, and for example, as a resin composite of a thermosetting resin and a thermoplastic resin, epoxy resin-PSF, epoxy resin-PPS, epoxy resin-PES, etc. can be used.
本発明に係る固着剤組成物および樹脂組成物には、その他の成分として、着色剤を配合することもできる。 A colorant may be added to the adhesive composition and the resin composition according to the present invention as another component.
着色剤としては、着色顔料や染料等としてカラーインデックスで表される公知慣用のものが使用可能である。例えば、Pigment Blue 15、15:1、15:2、15:3、15:4、15:6、16、60、Solvent Blue 35、63、68、70、83、87、94、97、122、136、67、70、Pigment Green 7、36、3、5、20、28、Solvent Yellow 163、Pigment Yellow 24、108、193、147、199、202、110、109、139、179、185、93、94、95、128、155、166、180、120、151、154、156、175、181、1、2、3、4、5、6、9、10、12、61、62、62:1、65、73、74、75、97、100、104、105、111、116、167、168、169、182、183、12、13、14、16、17、55、63、81、83、87、126、127、152、170、172、174、176、188、198、Pigment Orange 1、5、13、14、16、17、24、34、36、38、40、43、46、49、51、61、63、64、71、73、Pigment Red 1、2、3、4、5、6、8、9、12、14、15、16、17、21、22、23、31、32、112、114、146、147、151、170、184、187、188、193、210、245、253、258、266、267、268、269、37、38、41、48:1、48:2、48:3、48:4、49:1、49:2、50:1、52:1、52:2、53:1、53:2、57:1、58:4、63:1、63:2、64:1、68、171、175、176、185、208、123、149、166、178、179、190、194、224、254、255、264、270、272、220、144、166、214、220、221、242、168、177、216、122、202、206、207、209、Solvent Red 135、179、149、150、52、207、Pigment Violet 19、23、29、32、36、38、42、Solvent Violet 13、36、Pigment Brown 23、25、Pigment Black 1、7等が挙げられる。 As the coloring agent, known and commonly used coloring agents such as coloring pigments and dyes represented by a color index can be used. For example, Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 60, Solvent Blue 35, 63, 68, 70, 83, 87, 94, 97, 122, 136, 67, 70, Pigment Green 7, 36, 3, 5, 20, 28, Solvent Yellow 163, Pigment Yellow 24, 108, 193, 147, 199, 202, 110, 109, 139, 179, 185, 93 ,. 94, 95, 128, 155, 166, 180, 120, 151, 154, 156, 175, 181, 1, 2, 3, 4, 5, 6, 9, 10, 12, 61, 62, 62: 1, 65, 73, 74, 75, 97, 100, 104, 105, 111, 116, 167, 168, 169, 1 2, 183, 12, 13, 14, 16, 17, 55, 63, 81, 83, 87, 126, 127, 152, 170, 172, 174, 176, 188, 198, Pigment Orange 1, 5, 13, 14, 16, 17, 24, 34, 36, 38, 40, 43, 46, 49, 51, 61, 63, 64, 71, 73, Pigment Red 1, 2, 3, 4, 5, 6, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 112, 114, 146, 147, 151, 170, 184, 187, 188, 193, 210, 245, 253, 258, 266, 267, 268, 269, 37, 38, 41, 48: 1, 48: 2, 48: 3, 48: 4, 49: 1, 49: 2, 50: 1, 52: 1, 52: 2, 53: 1, 3: 2, 57: 1, 58: 4, 63: 1, 63: 2, 64: 1, 68, 171, 175, 176, 185, 208, 123, 149, 166, 178, 179, 190, 194, 224, 254, 255, 264, 270, 272, 220, 144, 166, 214, 220, 221, 242, 168, 177, 216, 122, 202, 206, 207, 209, Solvent Red 135, 179, 149, 150, 52, 207, Pigment Violet 19, 23, 29, 32, 36, 38, 42, Solvent Violet 13, 36, Pigment Brown 23, 25, Pigment Black 1, 7 and the like.
また、本発明に係る固着剤組成物および樹脂組成物には、必要に応じて、消泡・レベリング剤、チクソトロピー付与剤・増粘剤、カップリング剤、分散剤、難燃剤等の慣用の添加剤を含有させることができる。 Further, in the adhesive composition and the resin composition according to the present invention, if necessary, conventional additives such as defoaming / leveling agents, thixotropy-imparting agents / thickeners, coupling agents, dispersants, flame retardants, etc. are added. Agents can be included.
消泡剤・レベリング剤としては、鉱物油、植物油、脂肪族アルコール、脂肪酸、金属石鹸、脂肪酸アミド、ポリオキシアルキレングリコール、ポリオキシアルキレンアルキルエーテル、ポリオキシアルキレン脂肪酸エステル等の化合物等が使用できる。 As the defoaming agent / leveling agent, compounds such as mineral oil, vegetable oil, aliphatic alcohol, fatty acid, metal soap, fatty acid amide, polyoxyalkylene glycol, polyoxyalkylene alkyl ether, and polyoxyalkylene fatty acid ester can be used.
チクソトロピー付与剤・増粘剤としては、カオリナイト、スメクタイト、モンモリロナイト、ベントナイト、タルク、マイカ、ゼオライト等の粘土鉱物や、不定形無機粒子、ポリアミド系添加剤、変性ウレア系添加剤、ワックス系添加剤などが使用できる。 As thixotropy-imparting agents / thickeners, clay minerals such as kaolinite, smectite, montmorillonite, bentonite, talc, mica, zeolite, amorphous inorganic particles, polyamide-based additives, modified urea-based additives, wax-based additives Etc. can be used.
カップリング剤としては、アルコキシ基としてメトキシ基、エトキシ基、アセチル等であり、反応性官能基としてビニル、メタクリル、アクリル、エポキシ、環状エポキシ、メルカプト、アミノ、ジアミノ、酸無水物、ウレイド、スルフィド、イソシアネート等である、例えば、ビニルエトキシラン、ビニルトリメトキシシラン、ビニル・トリス(β―メトキシエトキシ)シラン、γ−メタクリロキシプロピルトリメトキシラン等のビニル系シラン化合物、γ−アミノプロピルトリメトキシラン、Ν―β―(アミノエチル)γ−アミノプロピルトリメトキシシラン、N−β−(アミノエチル)γ−アミノプロピルメチルジメトキシシラン、γ−ウレイドプロピルトリエトキシシラン等のアミノ系シラン化合物、γ−グリシドキシプロピルトリメトキシシラン、β―(3,4−エポキシシクロヘキシル)エチルトリメトキシラン、γ−グリシドキシプロピルメチルジエトキシシラン等のエポキシ系シラン化合物、γ−メルカプトプロピルトリメトキシシラン等のメルカプト系シラン化合物、Ν−フェニル−γ−アミノプロピルトリメトキシシラン等のフェニルアミノ系シラン化合物等のシランカップリング剤、イソプロピルトリイソステアロイル化チタネート、テトラオクチルビス(ジトリデシルホスファイト)チタネート、ビス(ジオクチルパイロホスフェート)オキシアセテートチタネート、イソプロピルトリドデシルベンゼンスルホニルチタネート、イソプロピルトリス(ジオクチルパイロホスフェート)チタネート、テトライソプロピルビス(ジオクチルホスファイト)チタネート、テトラ(1,1−ジアリルオキシメチル−1−ブチル)ビス−(ジトリデシル)ホスファイトチタネート、ビス(ジオクチルパイロホスフェート)エチレンチタネート、イソプロピルトリオクタノイルチタネート、イソプロピルジメタクリルイソステアロイルチタネート、イソプロピルトリステアロイルジアクリルチタネート、イソプロピルトリ(ジオクチルホスフェート)チタネート、イソプロピルトリクミルフェニルチタネート、ジクミルフェニルオキシアセテートチタネート、ジイソステアロイルエチレンチタネート等のチタネート系カップリング剤、エチレン性不飽和ジルコネート含有化合物、ネオアルコキシジルコネート含有化合物、ネオアルコキシトリスネオデカノイルジルコネート、ネオアルコキシトリス(ドデシル)ベンゼンスルホニルジルコネート、ネオアルコキシトリス(ジオクチル)ホスフェートジルコネート、ネオアルコキシトリス(ジオクチル)ピロホスフェートジルコネート、ネオアルコキシトリス(エチレンジアミノ)エチルジルコネート、ネオアルコキシトリス(m−アミノ)フェニルジルコネート、テトラ(2,2−ジアリルオキシメチル)ブチル,ジ(ジトリデシル)ホスフィトジルコネート、ネオペンチル(ジアリル)オキシ,トリネオデカノイルジルコネート、ネオペンチル(ジアリル)オキシ,トリ(ドデシル)ベンゼン−スルホニルジルコネート、ネオペンチル(ジアリル)オキシ,トリ(ジオクチル)ホスファトジルコネート、ネオペンチル(ジアリル)オキシ,トリ(ジオクチル)ピロ−ホスファトジルコネート、ネオペンチル(ジアリル)オキシ,トリ(N−エチレンジアミノ)エチルジルコネート、ネオペンチル(ジアリル)オキシ,トリ(m−アミノ)フェニルジルコネート、ネオペンチル(ジアリル)オキシ,トリメタクリルジルコネート、ネオペンチル(ジアリル)オキシ,トリアクリルジルコネート、ジネオペンチル(ジアリル)オキシ,ジパラアミノベンゾイルジルコネート、ジネオペンチル(ジアリル)オキシ,ジ(3−メルカプト)プロピオニックジルコネート、ジルコニウム(IV)2,2−ビス(2−プロペノラトメチル)ブタノラト,シクロジ[2,2−(ビス2−プロペノラトメチル)ブタノラト]ピロホスファト−O,O等のジルコネート系カップリング剤、ジイソブチル(オレイル)アセトアセチルアルミネート、アルキルアセトアセテートアルミニウムジイソプロピレート等のアルミネート系カップリング剤等が使用できる。 The coupling agent is a methoxy group, an ethoxy group, acetyl or the like as an alkoxy group, and a vinyl, methacryl, acryl, epoxy, cyclic epoxy, mercapto, amino, diamino, acid anhydride, ureide, sulfide as a reactive functional group. Isocyanates and the like, for example, vinyl silane, vinyl trimethoxysilane, vinyl trimethoxysilane, vinyl tris (β-methoxyethoxy) silane, γ-methacryloxypropyltrimethoxylane, and other silane compounds, γ-aminopropyltrimethoxylane, Amino-based silane compounds such as Ν-β- (aminoethyl) γ-aminopropyltrimethoxysilane, N-β- (aminoethyl) γ-aminopropylmethyldimethoxysilane and γ-ureidopropyltriethoxysilane, γ-glycid Xypropyl propylamine Silanes, epoxy-based silane compounds such as β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, γ-glycidoxypropylmethyldiethoxysilane, mercapto-based silane compounds such as γ-mercaptopropyltrimethoxysilane, Ν- Silane coupling agents such as phenylamino-based silane compounds such as phenyl-γ-aminopropyltrimethoxysilane, isopropyltriisostearoylated titanate, tetraoctylbis (ditridecylphosphite) titanate, bis (dioctylpyrophosphate) oxyacetate titanate , Isopropyl tridodecylbenzenesulfonyl titanate, isopropyl tris (dioctyl pyrophosphate) titanate, tetraisopropyl bis (dioctyl phosphite) titanate, te La (1,1-diallyloxymethyl-1-butyl) bis- (ditridecyl) phosphite titanate, bis (dioctyl pyrophosphate) ethylene titanate, isopropyl trioctanoyl titanate, isopropyl dimethacryl isostearoyl titanate, isopropyl tristearoyl diacryl Titanate coupling agents such as titanate, isopropyl tri (dioctyl phosphate) titanate, isopropyl tricumyl phenyl titanate, dicumyl phenyloxyacetate titanate, diisostearoyl ethylene titanate, ethylenically unsaturated zirconate containing compounds, neoalkoxy zirconate containing compounds. , Neoalkoxy tris neodecanoyl zirconate, neoalkoxy tris (dodecyl) benzenes Ruphonyl zirconate, neoalkoxy tris (dioctyl) phosphate zirconate, neoalkoxy tris (dioctyl) pyrophosphate zirconate, neoalkoxy tris (ethylenediamino) ethyl zirconate, neoalkoxy tris (m-amino) phenyl zirconate, tetra (2,2-Diallyloxymethyl) butyl, di (ditridecyl) phosphite zirconate, neopentyl (diallyl) oxy, trineodecanoyl zirconate, neopentyl (diallyl) oxy, tri (dodecyl) benzene-sulfonyl zirconate, neopentyl (Diallyl) oxy, tri (dioctyl) phosphato zirconate, neopentyl (diallyl) oxy, tri (dioctyl) pyro-phosphato zirconate, neopentyl (di Ryl) oxy, tri (N-ethylenediamino) ethyl zirconate, neopentyl (diallyl) oxy, tri (m-amino) phenyl zirconate, neopentyl (diallyl) oxy, trimethacryl zirconate, neopentyl (diallyl) oxy, triacryl Zirconate, Dineopentyl (diallyl) oxy, Diparaaminobenzoyl zirconate, Dineopentyl (diallyl) oxy, Di (3-mercapto) propionic zirconate, Zirconium (IV) 2,2-bis (2-propenolate methyl) Zirconate coupling agents such as butanolato, cyclodi [2,2- (bis2-propenolatomethyl) butanolato] pyrophosphato-O, O, diisobutyl (oleyl) acetoacetylaluminate, alkylacetoacetate Diisopropylate aluminate coupling agents such like.
分散剤としては、ポリカルボン酸系、ナフタレンスルホン酸ホルマリン縮合系、ポリエチレングリコール、ポリカルボン酸部分アルキルエステル系、ポリエーテル系、ポリアルキレンポリアミン系等の高分子型分散剤、アルキルスルホン酸系、四級アンモニウム系、高級アルコールアルキレンオキサイド系、多価アルコールエステル系、アルキルポリアミン系等の低分子型分散剤等が使用できる。 Examples of the dispersant include polycarboxylic acid type, naphthalene sulfonic acid formalin condensation type, polyethylene glycol, polycarboxylic acid partial alkyl ester type, polyether type, polyalkylene polyamine type and the like polymeric dispersants, alkyl sulfonic acid type, four A low molecular type dispersant such as a quaternary ammonium type, a higher alcohol alkylene oxide type, a polyhydric alcohol ester type or an alkyl polyamine type can be used.
難燃剤としては、水酸化アルミニウム、水酸化マグネシウム等の水和金属系、赤燐、燐酸アンモニウム、炭酸アンモニウム、ホウ酸亜鉛、錫酸亜鉛、モリブデン化合物系、臭素化合物系、塩素化合物系、燐酸エステル、含燐ポリオール、含燐アミン、メラミンシアヌレート、メラミン化合物、トリアジン化合物、グアニジン化合物、シリコーンポリマー等が使用できる。 Examples of flame retardants include hydrated metal compounds such as aluminum hydroxide and magnesium hydroxide, red phosphorus, ammonium phosphate, ammonium carbonate, zinc borate, zinc stannate, molybdenum compound system, bromine compound system, chlorine compound system, phosphate ester. , Phosphorus-containing polyols, phosphorus-containing amines, melamine cyanurate, melamine compounds, triazine compounds, guanidine compounds, silicone polymers and the like can be used.
本発明に係る固着剤組成物および樹脂組成物は、その他、硫酸バリウム、シリカ、ハイドロタルサイト等の無機フィラー、ナイロンパウダー、フッ素パウダー等の有機フィラー、ラジカル補捉剤、紫外線吸収剤、過酸化物分解剤、熱重合禁止剤、密着促進剤、防錆剤、表面処理剤、界面活性剤、潤滑剤、帯電防止剤、pH調整剤、酸化防止剤、染料、顔料、蛍光剤等を、本発明の目的を阻害しない範囲で含んでいてもよい。 The adhesive composition and the resin composition according to the present invention are also inorganic fillers such as barium sulfate, silica and hydrotalcite, nylon powders, organic fillers such as fluorine powder, radical scavengers, ultraviolet absorbers and peroxides. Material decomposition agents, thermal polymerization inhibitors, adhesion promoters, rust preventives, surface treatment agents, surfactants, lubricants, antistatic agents, pH adjusters, antioxidants, dyes, pigments, fluorescent agents, etc. It may be contained within a range that does not impair the object of the invention.
[貯蔵弾性率]
本発明においては、固着剤2の貯蔵弾性率が、樹脂3の貯蔵弾性率よりも高いことが必要である。ここで、固着剤2の貯蔵弾性率とは、繊維1は含まずに、固着剤組成物の成分のみの配合物を、成膜後に熱または光により硬化させた硬化膜の貯蔵弾性率を意味する。同様に、樹脂3の貯蔵弾性率についても、硬化性樹脂の場合には成膜後に熱または光により硬化させた硬化膜の貯蔵弾性率を意味し、熱可塑性樹脂の場合には、溶融成膜後に溶剤を除去して得られる塗膜の貯蔵弾性率を意味する。また、貯蔵弾性率とは、試料の硬さの一指標値であって、一定の温度変化を加えながら試料に対し周期的な荷重をかけて歪を検出する動的粘弾性測定と呼ばれる評価を行って、検出した歪から算出される値であり、この値が高いほど優れた力学強度を示していることを意味する。本発明においては、いずれかの温度において、固着剤2の貯蔵弾性率が樹脂3の貯蔵弾性率よりも高いものであればよく、その好適範囲は、固着剤2の貯蔵弾性率については30〜0.1GPaであり、より好ましくは20〜0.5GPaであり、樹脂3の貯蔵弾性率については10〜0.001GPaであり、より好ましくは5〜0.01GPaであり、いずれかの温度において、固着剤2の貯蔵弾性率が樹脂3の貯蔵弾性率よりも0.1GPa以上大きいことが好ましい。特には、150〜250℃の範囲内のいずれかの温度において、固着剤2の貯蔵弾性率が、樹脂3の貯蔵弾性率よりも高いことが好ましく、150〜250℃の全温度範囲において、固着剤2の貯蔵弾性率が、樹脂3の貯蔵弾性率よりも高いことがより好ましい。これにより、本発明の樹脂含有シートは、150〜250℃の高温領域でも使用可能となるので、用途が広がることから、好ましい。[Storage modulus]
In the present invention, the storage elastic modulus of the adhesive 2 needs to be higher than the storage elastic modulus of the resin 3. Here, the storage elastic modulus of the adhesive agent 2 means the storage elastic modulus of a cured film obtained by curing the composition containing only the components of the adhesive composition without the fiber 1 after the film formation by heat or light. To do. Similarly, regarding the storage elastic modulus of the resin 3, in the case of a curable resin, it means the storage elastic modulus of a cured film cured by heat or light after film formation, and in the case of a thermoplastic resin, a melt film formation. It means the storage elastic modulus of a coating film obtained by removing the solvent later. Further, the storage elastic modulus is an index value of hardness of a sample, and an evaluation called dynamic viscoelasticity measurement in which a cyclic load is applied to the sample while a constant temperature change is applied to detect strain is used. It is a value calculated from the detected strain, and it means that the higher this value is, the more excellent the mechanical strength is. In the present invention, the storage elastic modulus of the adhesive agent 2 may be higher than the storage elastic modulus of the resin 3 at any temperature, and the preferable range thereof is 30 to 30 for the adhesive agent 2. 0.1 GPa, more preferably 20 to 0.5 GPa, the storage elastic modulus of the resin 3 is 10 to 0.001 GPa, more preferably 5 to 0.01 GPa, at any temperature, It is preferable that the storage elastic modulus of the adhesive 2 is larger than that of the resin 3 by 0.1 GPa or more. In particular, it is preferable that the storage elastic modulus of the adhesive 2 is higher than the storage elastic modulus of the resin 3 at any temperature within the range of 150 to 250 ° C., and in the entire temperature range of 150 to 250 ° C. It is more preferable that the storage elastic modulus of the agent 2 is higher than the storage elastic modulus of the resin 3. As a result, the resin-containing sheet of the present invention can be used even in a high temperature range of 150 to 250 ° C., so that the application is widened, which is preferable.
[ガラス転移温度]
本発明においては、固着剤2のガラス転移温度が、樹脂3のガラス転移温度または軟化温度よりも高いことが好ましい。ここで、固着剤2のガラス転移温度とは、繊維1は含まずに、固着剤組成物の成分のみの配合物を、成膜後に熱または光により硬化させた硬化膜のガラス転移温度を意味する。同様に、樹脂3のガラス転移温度または軟化温度についても、硬化性樹脂の場合には成膜後に熱または光により硬化させた硬化膜のガラス転移温度を意味し、熱可塑性樹脂の場合には、溶融成膜後に溶剤を除去して得られる塗膜の軟化温度を意味する。また、ガラス転移温度とは、前述の動的粘弾性測定から得られた貯蔵弾性率(E′)と損失弾性率(E″)の比(E″/E′)から算出される値(損失正接)が最大のときの温度のことであり、この温度が高いほど優れた耐熱性を示していることを意味する。本発明においては、ガラス転移温度の上限については特に制限されないが、その好適範囲は、固着剤2のガラス転移温度については130℃以上であり、より好ましくは140℃以上であり、特に好ましくは250℃以上である。固着剤2のガラス転移温度が高いほど、本発明の樹脂含有シートの貯蔵弾性率が高くなるので好ましい。
一方、樹脂3のガラス転移温度または軟化温度については70℃以上であり、より好ましくは80℃以上である。また、固着剤2のガラス転移温度が樹脂3のガラス転移温度または軟化温度よりも5℃以上大きいことが好ましい。[Glass-transition temperature]
In the present invention, the glass transition temperature of the adhesive 2 is preferably higher than the glass transition temperature or softening temperature of the resin 3. Here, the glass transition temperature of the adhesive agent 2 means the glass transition temperature of a cured film obtained by curing a composition containing only the components of the adhesive agent composition without including the fiber 1 after the film formation by heat or light. To do. Similarly, regarding the glass transition temperature or softening temperature of the resin 3, in the case of a curable resin, it means the glass transition temperature of a cured film cured by heat or light after film formation, and in the case of a thermoplastic resin, It means the softening temperature of the coating film obtained by removing the solvent after the melt film formation. The glass transition temperature is a value (loss) calculated from the ratio (E ″ / E ′) of the storage elastic modulus (E ′) and the loss elastic modulus (E ″) obtained from the dynamic viscoelasticity measurement described above. Tangent) is the maximum temperature, and the higher this temperature is, the better the heat resistance is. In the present invention, the upper limit of the glass transition temperature is not particularly limited, but the preferred range is 130 ° C. or higher, more preferably 140 ° C. or higher, particularly preferably 250 ° C. for the glass transition temperature of the adhesive 2. ℃ or above. The higher the glass transition temperature of the fixing agent 2, the higher the storage elastic modulus of the resin-containing sheet of the present invention, which is preferable.
On the other hand, the glass transition temperature or softening temperature of the resin 3 is 70 ° C. or higher, and more preferably 80 ° C. or higher. Further, it is preferable that the glass transition temperature of the adhesive 2 is 5 ° C. or more higher than the glass transition temperature or the softening temperature of the resin 3.
[樹脂含有シートの製造]
本発明の樹脂含有シートは、繊維基材11を固着剤組成物で処理して繊維1同士を固着させた後、固着された繊維基材11に樹脂組成物を含浸することにより、得ることができる。本発明の樹脂含有シートは、例えば、キャリアフィルム等の被塗布物上に繊維を配置した状態で、固着剤組成物および樹脂組成物を順次塗布、含浸させて、固着剤組成物および樹脂組成物中に含まれる有機溶媒を揮発乾燥することにより、ドライフィルムとして製造することもでき、所望に応じ、さらに、その上にカバーフィルムを貼り合わせてもよい。この際、樹脂組成物が、固着剤組成物の繊維に対する固着性能を阻害するものでなければ、樹脂組成物の塗布プロセスは、固着剤の乾燥前であっても乾燥後であっても、いずれでもよい。[Production of resin-containing sheet]
The resin-containing sheet of the present invention can be obtained by treating the
この場合、本発明の固着剤組成物および樹脂組成物は、必要に応じ、各成分を配合、分散、希釈して、塗布方法に適した粘度に調整し、塗布することができる。上述したように、固着剤組成物については、繊維基材11に浸透させて繊維1同士を固着させることができるものであればよく、また、樹脂組成物については、繊維基材11の少なくとも一方の面、特には両方の面を、金属箔等に対し密着させることができるものであればよい。
In this case, the adhesive composition and the resin composition of the present invention can be coated by adjusting the viscosity suitable for the coating method by blending, dispersing, and diluting each component, if necessary. As described above, the adhesive composition may be one that can be penetrated into the
被塗布物としては、ドライフィルム用のキャリアフィルムが好ましいが、金属箔表面や回路形成された配線板表面に直接塗布してもよい。塗布方法の具体例としては、ピペット等を用いた滴下法、ディップコート法、バーコーター法、スピンコート法、カーテンコート法、スプレーコート法、ロールコート法、スリットコート法、ブレードコート法、リップコート法、コンマコート法、フィルムコート法等の各種コート法や、スクリーン印刷、スプレー印刷、インクジェット印刷、凸版印刷、凹版印刷、平版印刷等の各種印刷法が挙げられる。 A carrier film for a dry film is preferable as the article to be coated, but it may be directly coated on the surface of the metal foil or the surface of the circuit-formed wiring board. Specific examples of the coating method include a dropping method using a pipette, a dip coating method, a bar coater method, a spin coating method, a curtain coating method, a spray coating method, a roll coating method, a slit coating method, a blade coating method, a lip coating method. And various coating methods such as a comma coating method and a film coating method, and various printing methods such as screen printing, spray printing, inkjet printing, letterpress printing, intaglio printing, and lithographic printing.
また、キャリアフィルムとカバーフィルムとは、ドライフィルムに用いられる材料として公知のものを、いずれも使用することができ、例えば、ポリエチレンフィルム、ポリプロピレンフィルム等が挙げられる。キャリアフィルムとカバーフィルムとは、同一のフィルム材料を用いても、異なるフィルム材料を用いてもよいが、カバーフィルムについては、樹脂3との接着性が、キャリアフィルムよりも小さいものが好ましい。 As the carrier film and the cover film, known materials used for the dry film can be used, and examples thereof include a polyethylene film and a polypropylene film. The carrier film and the cover film may use the same film material or different film materials, but it is preferable that the cover film has a smaller adhesiveness with the resin 3 than the carrier film.
本発明の樹脂含有シートを基板に密着させることで、構造体を得ることができる。基板としては、金属箔基板や、回路基板(回路形成された配線板)などが挙げられる。本発明の樹脂含有シートを基板表面に熱密着させることで、樹脂絶縁層を形成することができ、その繰り返しにより、金属箔層と樹脂絶縁層とをそれぞれ複数層で積層することもできる。なお、樹脂含有シートは、キャリアフィルム上で製造した際に、樹脂含有シート同士で積層してもよく、金属箔等との密着時に樹脂含有シート同士で積層してもよい。 A structure can be obtained by bringing the resin-containing sheet of the present invention into close contact with the substrate. Examples of the substrate include a metal foil substrate and a circuit substrate (circuit-formed wiring board). The resin-containing sheet of the present invention can be thermally adhered to the surface of the substrate to form a resin insulating layer, and by repeating the process, the metal foil layer and the resin insulating layer can be laminated in a plurality of layers. It should be noted that the resin-containing sheet may be laminated with the resin-containing sheets when it is manufactured on the carrier film, or may be laminated with the resin-containing sheets when they are adhered to a metal foil or the like.
本発明の樹脂含有シートを用いて構造体を作製する際に、固着剤組成物および樹脂組成物が熱硬化性樹脂ないし光硬化性樹脂の組合せである場合には、加熱硬化のみの方法、活性エネルギー線照射のみの方法、活性エネルギー線の照射後に加熱硬化させる方法、または、加熱硬化後に活性エネルギー線を照射する方法を用いることで、構造体を作製することができる。また、ドライフィルムを用いる場合には、カバーフィルムがある場合にはカバーフィルムを剥がして、基板表面に樹脂含有シートを熱密着させ、次いで、キャリアフィルムを剥がし、上記硬化方法により硬化させて、構造体を製造することができる。なお、固着剤組成物および樹脂組成物として、ともに熱硬化性樹脂を用いる場合には、繊維同士の固着および樹脂の含浸の、双方の加熱硬化プロセスを同時に実施してもよい。また、加熱を行う際の加熱温度については、目的とする基材に含まれる繊維や固着剤が高熱により分解しない範囲であれば、特に下限および上限の制限はなく、活性エネルギー線照射を行う際の露光量についても、露光量が低すぎて未硬化部分が生ずることがなければ、特に下限および上限の制限はない。 When a structure is produced using the resin-containing sheet of the present invention, when the adhesive composition and the resin composition are a combination of a thermosetting resin or a photocurable resin, only a method of heat curing, the activity A structure can be manufactured by using a method of only irradiation with energy rays, a method of heating and curing after irradiation of active energy rays, or a method of irradiating with active energy rays after heating and curing. When a dry film is used, the cover film is peeled off if there is a cover film, the resin-containing sheet is heat-adhered to the substrate surface, then the carrier film is peeled off, and the composition is cured by the above-mentioned curing method. The body can be manufactured. When a thermosetting resin is used as both the adhesive composition and the resin composition, both heat curing processes of fixing the fibers to each other and impregnating the resin may be performed at the same time. Regarding the heating temperature when performing heating, there is no particular lower limit or upper limit as long as the fibers and the adhesive contained in the target substrate are not decomposed by high heat, and when performing active energy ray irradiation. With respect to the exposure amount, the lower limit and the upper limit are not particularly limited as long as the exposure amount is too low and an uncured portion does not occur.
また、本発明の樹脂含有シートを作製する際に、樹脂組成物が熱可塑性樹脂である場合には、ペレット形状やシート形状の熱可塑性樹脂を加熱または加熱、圧着する手法を用いることもできる。ここで、熱可塑性樹脂を、固着剤により固着した繊維基材内に含浸させるためには、装置を用いて加圧することは必須要件ではないが、加圧を行うことにより熱可塑性樹脂の繊維基材内への浸入がより容易となる。加圧を行う場合、目的とする樹脂含有シートの形状を損なわない限り、特に圧力の上限はない。この樹脂含有シートを基体表面に熱密着することにより、構造体を成形することができる。また、ドライフィルムを用いて構造体を成形する際には、前記同様に作製することができる。 Further, when the resin-containing sheet of the present invention is produced, when the resin composition is a thermoplastic resin, a method of heating or heating and press-bonding the pellet-shaped or sheet-shaped thermoplastic resin can also be used. Here, in order to impregnate the thermoplastic resin into the fibrous base material fixed by the fixing agent, it is not essential to apply pressure using a device, but by applying pressure, the fiber base of the thermoplastic resin Penetration into the material becomes easier. When applying pressure, there is no particular upper limit to the pressure as long as the intended shape of the resin-containing sheet is not impaired. The structure can be molded by thermally adhering the resin-containing sheet to the surface of the substrate. Further, when the structure is molded using the dry film, it can be manufactured in the same manner as described above.
なお、上記において、乾燥時、加熱硬化時または加熱加圧時に用いられる装置としては、熱風循環式乾燥炉、IR炉、ホットプレート、コンベクションオーブン、加熱・加圧ロール、プレス機等が挙げられる。また、活性エネルギー線照射の光源としては、低圧水銀灯、中圧水銀灯、高圧水銀灯、超高圧水銀灯、キセノンランプ、メタルハライドランプなどが挙げられる。その他、レーザー光線なども活性エネルギー線として利用できる。 In addition, in the above, as an apparatus used at the time of drying, heat-hardening, or heat-pressurizing, a hot air circulation type drying furnace, an IR furnace, a hot plate, a convection oven, a heating / pressurizing roll, a press machine, etc. can be mentioned. Examples of the light source for active energy ray irradiation include a low pressure mercury lamp, a medium pressure mercury lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a xenon lamp, and a metal halide lamp. In addition, a laser beam or the like can be used as the active energy ray.
本発明の樹脂含有シートの構成部材である繊維基材、繊維同士を固着剤により固着したもの(以下、「中間体」とも称する)、および、ドライフィルムの厚みについては、特に限定されず、目的に応じて適宜選択することができるが、特に中間体については、固着剤により繊維同士が互いに固着されているものであればよいので、その厚みは、繊維基材の厚みと同等、または、繊維基材の厚みの2倍を超えない程度の膜厚であることが好ましい。具体的には、繊維基材の厚みの1〜1.5倍の範囲内であることがより好ましい。中間体の厚みが繊維基材の厚みの2倍を超えると、固着剤そのものの物性の影響が出るため、好ましくない。 The thickness of the dry film is not particularly limited, with regard to the fiber base material that is a constituent member of the resin-containing sheet of the present invention, one in which fibers are fixed to each other with a fixing agent (hereinafter, also referred to as “intermediate”), and the thickness of the dry film. It can be appropriately selected depending on, but especially for the intermediate, as long as the fibers are fixed to each other by a fixing agent, its thickness is equal to the thickness of the fiber base material, or the fiber It is preferable that the thickness is not more than twice the thickness of the base material. Specifically, it is more preferably within the range of 1 to 1.5 times the thickness of the fiber base material. When the thickness of the intermediate body exceeds twice the thickness of the fiber base material, the physical properties of the adhesive itself are affected, which is not preferable.
本発明の樹脂含有シートを基板表面に形成し、硬化または成形して得られる構造体は、配線板用のコア材として使用することができ、エッチング処理等を行うことで、配線板用の層間絶縁材として使用することもできる。また、樹脂含有シートを回路形成された配線板表面に形成し、回路配線のみを覆うようにパターニング処理および硬化または成形して構造体とすれば、配線板の最外層であるソルダーレジスト等として使用することもできる。 The structure obtained by forming the resin-containing sheet of the present invention on the surface of a substrate and curing or molding it can be used as a core material for a wiring board, and by performing an etching treatment or the like, an interlayer for the wiring board can be obtained. It can also be used as an insulating material. Also, if a resin-containing sheet is formed on the surface of a wiring board on which a circuit is formed, and a patterning treatment and curing or molding is performed so as to cover only the circuit wiring to form a structure, it is used as a solder resist, which is the outermost layer of the wiring board. You can also do it.
以上説明したような構成の本発明の樹脂含有シートは、電子機器用の配線板等に適用することができ、例えば、配線板用の層間絶縁材やソルダーレジスト、コア材等に好適に適用することができ、これにより、本発明の所期の効果を得ることができるものである。その他、例えば、繊維同士を固着剤組成物で固着し、樹脂を浸透、乾燥させて、半硬化である状態(Bステージ)の樹脂絶縁層を形成し、樹脂絶縁層と金属箔を積層プレスすることで、多層板を作製することもできる。 The resin-containing sheet of the present invention having the above-described structure can be applied to a wiring board or the like for electronic devices, and is preferably applied to, for example, an interlayer insulating material for a wiring board, a solder resist, or a core material. Therefore, the intended effect of the present invention can be obtained. In addition, for example, the fibers are fixed to each other with a fixing agent composition, the resin is permeated and dried to form a resin insulating layer in a semi-cured state (B stage), and the resin insulating layer and the metal foil are laminated and pressed. Thus, a multi-layer board can be manufactured.
以下、実施例、参考例および比較例により本発明をさらに詳細に説明するが、本発明は、これら実施例、参考例および比較例によって制限されるものではない。なお、以下の表中の配合量は、すべて質量部を示す。 Hereinafter, the present invention will be described in more detail with reference to Examples, Reference Examples and Comparative Examples, but the present invention is not limited to these Examples, Reference Examples and Comparative Examples. In addition, all the compounding amounts in the following tables indicate parts by mass.
[ポリアミック酸ワニス1の合成]
窒素置換させた攪拌機付属の三つ口フラスコに、脱水N−メチル−2−ピロリドン(NMP)溶媒(和光純薬工業(株)製)を入れ、4,4’−ジアミノジフェニルエーテル(ODA)(和光純薬工業(株)製)と1,2,4,5−ベンゼンテトラカルボン酸二無水物(PMDA)(和光純薬工業(株)製)とを1:1のモル比で配合し、室温で16時間以上撹拌して、樹脂固形分割合が7.5質量%であるポリアミック酸ワニス1を得た。[Synthesis of polyamic acid varnish 1]
A dehydrated N-methyl-2-pyrrolidone (NMP) solvent (manufactured by Wako Pure Chemical Industries, Ltd.) was placed in a three-necked flask equipped with a stirrer that had been replaced with nitrogen, and 4,4′-diaminodiphenyl ether (ODA) (wa Kou Pure Chemical Industries, Ltd.) and 1,2,4,5-benzenetetracarboxylic dianhydride (PMDA) (Wako Pure Chemical Industries, Ltd.) were mixed at a molar ratio of 1: 1 at room temperature. After stirring for 16 hours or more, a polyamic acid varnish 1 having a resin solid content ratio of 7.5 mass% was obtained.
[ポリアミック酸ワニス2の合成]
窒素置換させた攪拌機付属の三つ口フラスコに、脱水N−メチル−2−ピロリドン(NMP)溶媒(和光純薬工業(株)製)を入れ、p−フェニレンジアミン(PDA)(和光純薬工業(株)製)と、3,3’,4,4’−ビフェニルテトラカルボン酸無水物(BPDA)(和光純薬工業(株)製)とを1:1のモル比で配合し、室温で16時間以上撹拌して、樹脂固形分割合が7.5質量%であるポリアミック酸ワニス2を得た。[Synthesis of Polyamic Acid Varnish 2]
A dehydrated N-methyl-2-pyrrolidone (NMP) solvent (manufactured by Wako Pure Chemical Industries, Ltd.) was placed in a three-necked flask equipped with a stirrer that was purged with nitrogen, and p-phenylenediamine (PDA) (Wako Pure Chemical Industries, Ltd.) Co., Ltd.) and 3,3 ′, 4,4′-biphenyltetracarboxylic acid anhydride (BPDA) (manufactured by Wako Pure Chemical Industries, Ltd.) at a molar ratio of 1: 1 and mixed at room temperature. After stirring for 16 hours or more, a polyamic acid varnish 2 having a resin solid content ratio of 7.5 mass% was obtained.
[固着剤組成物または樹脂組成物の調製]
下記表1中に、固着剤組成物または樹脂組成物として使用される組成物1〜4の配合内容を示す。下記表1中の組成物1〜4の記載に従い、各組成物を調製した。組成物1の複数成分系の場合は、各成分を配合した後、自転・公転ミキサーを用いて攪拌し、調製した。[Preparation of adhesive composition or resin composition]
Table 1 below shows the content of the compositions 1 to 4 used as the adhesive composition or the resin composition. Each composition was prepared according to the description of compositions 1 to 4 in Table 1 below. In the case of the multi-component system of the composition 1, the components were blended and then prepared by stirring using a rotation / revolution mixer.
[固着剤または樹脂の貯蔵弾性率等評価用試験片の作製]
各組成物1〜4をそれぞれ、厚さ18μmの銅箔にアプリケーターを用いて塗布し、塗膜を得た。
組成物1については、熱風循環式乾燥炉で80℃、30分間の大気条件下で乾燥後、150℃、60分間の大気条件下で加熱させてエポキシ樹脂硬化物を得た。銅箔を除去したところ、厚みは50μmであった。この硬化物を用いて、幅5mm、長さ50mmの貯蔵弾性率等評価用試験片を作製した。
組成物2については、塗布後、熱風循環式乾燥炉で80℃、30分間の大気条件下で乾燥後、250℃、60分間の窒素条件下(100ml/min.)で加熱してイミド化物を得た。銅箔を除去したところ、厚みは50μmであった。その後、上記と同様にして評価用試験片を作製した。
組成物3については、加熱操作を300℃、60分間の窒素条件下で行った以外は組成物2と同様にして評価用試験片を作製した。
組成物4については、高密度ポリエチレンペレット(比重0.95)をプレス機に適量投入して、140℃、3MPa、3分間加熱加圧後、室温まで冷却して成形体を得た後に個片化したところ、厚みは50μmであった。その後、上記と同様にして評価用試験片を作製した。[Preparation of test piece for evaluation of storage elastic modulus of adhesive or resin]
Each of the compositions 1 to 4 was applied to a copper foil having a thickness of 18 μm using an applicator to obtain a coating film.
The composition 1 was dried in a hot air circulation type drying oven at 80 ° C. for 30 minutes under atmospheric conditions and then heated at 150 ° C. for 60 minutes under atmospheric conditions to obtain an epoxy resin cured product. When the copper foil was removed, the thickness was 50 μm. Using this cured product, a test piece for evaluation such as storage elastic modulus having a width of 5 mm and a length of 50 mm was prepared.
With regard to the composition 2, after coating, it was dried in a hot-air circulation type drying oven at 80 ° C. for 30 minutes under atmospheric conditions, and then heated at 250 ° C. for 60 minutes under nitrogen conditions (100 ml / min.) To give an imidized product. Obtained. When the copper foil was removed, the thickness was 50 μm. Then, an evaluation test piece was prepared in the same manner as above.
With respect to the composition 3, a test piece for evaluation was prepared in the same manner as the composition 2 except that the heating operation was performed under a nitrogen condition at 300 ° C. for 60 minutes.
With regard to the composition 4, high-density polyethylene pellets (specific gravity 0.95) were put into a press in an appropriate amount, heated and pressurized at 140 ° C. for 3 MPa for 3 minutes, and then cooled to room temperature to obtain a molded body, which was then cut into individual pieces. As a result, the thickness was 50 μm. Then, an evaluation test piece was prepared in the same manner as above.
[樹脂含有シートおよびシートについての貯蔵弾性率評価用試験片の作製]
下記表2,3中に、各実施例、参考例および比較例の樹脂含有シートないしシートの構成を示す。
[Production of resin-containing sheet and test piece for evaluating storage elastic modulus of sheet]
Tables 2 and 3 below show the configurations of the resin-containing sheets or sheets of Examples, Reference Examples and Comparative Examples.
(実施例1−Aの中間体の作製)
下記表2中の実施例1−Aについては、繊維基材としてガラスクロス(タイプ1035(IPC規格)、厚み30μm)を用いて、ここに、上記組成物1(粘度0.0005Pa・s)を含浸させた後、熱風循環式乾燥炉で80℃、30分間の大気条件下で乾燥後、150℃、60分間で加熱硬化させて、ガラスクロスおよび固着剤(エポキシ樹脂組成物の硬化物)からなる中間体を作製した。(Preparation of Intermediate of Example 1-A)
For Example 1-A in Table 2 below, a glass cloth (type 1035 (IPC standard), thickness 30 μm) was used as the fiber substrate, and the composition 1 (viscosity 0.0005 Pa · s) was added thereto. After impregnation, it is dried in a hot air circulation type drying oven at 80 ° C. for 30 minutes under atmospheric conditions, and then heat-cured at 150 ° C. for 60 minutes to remove the glass cloth and the adhesive (cured product of the epoxy resin composition). The following intermediate was prepared.
(実施例2−Aの中間体の作製)
下記表2中の実施例2−Aについては、実施例1−Aと同様のガラスクロスに、上記組成物2(粘度0.001Pa・s)を含浸させた後、熱風循環式乾燥炉で80℃、30分間の大気条件下で乾燥後、250℃、60分間で加熱してイミド化し、ガラスクロスおよび固着剤(ポリイミド)からなる中間体を作製した。(Preparation of intermediate of Example 2-A)
Regarding Example 2-A in Table 2 below, the same glass cloth as in Example 1-A was impregnated with the above composition 2 (viscosity 0.001 Pa · s), and then 80 in a hot air circulation drying furnace. After drying under atmospheric conditions at 30 ° C. for 30 minutes, it was heated at 250 ° C. for 60 minutes to imidize to prepare an intermediate body composed of glass cloth and a fixing agent (polyimide).
(実施例3−Aの中間体の作製)
下記表2中の実施例3−Aについては、実施例1−Aと同様のガラスクロスに、上記組成物3(粘度0.001Pa・s)を含浸させた後、熱風循環式乾燥炉で80℃、30分間の大気条件下で乾燥後、300℃、60分間で加熱してイミド化し、ガラスクロスおよび固着剤(ポリイミド)からなる中間体を作製した。(Preparation of intermediate of Example 3-A)
Regarding Example 3-A in Table 2 below, the same glass cloth as in Example 1-A was impregnated with the above composition 3 (viscosity 0.001 Pa · s), and then 80 in a hot air circulation type drying furnace. After drying under atmospheric conditions at 30 ° C. for 30 minutes, it was imidized by heating at 300 ° C. for 60 minutes to prepare an intermediate body composed of glass cloth and a fixing agent (polyimide).
(比較例4−Aの中間体の作製)
実施例1−Aと同様に、上記組成物1を使用してガラスクロスおよび固着剤(エポキシ樹脂組成物の硬化物)からなる中間体を作製した。(Preparation of Intermediate of Comparative Example 4-A)
In the same manner as in Example 1-A, the above composition 1 was used to prepare an intermediate body composed of a glass cloth and a fixing agent (cured product of epoxy resin composition).
実施例1−A〜3−Aおよび比較例4−Aの各中間体の厚みは33〜35μmであり、ガラスクロスの厚みからの厚みの増大は3〜5μmとわずかだった。 The thickness of each intermediate of Examples 1-A to 3-A and Comparative Example 4-A was 33 to 35 μm, and the increase in the thickness from the thickness of the glass cloth was a slight 3 to 5 μm.
(参考例1−Bの中間体の作製)
下記表3中の参考例1−Bについては、繊維としてアラミド不織布(ノーメックス410、厚み50μm)を用いたこと以外は、実施例1−Aの中間体の作製と同様に処理して、アラミド不織布および固着剤(エポキシ樹脂組成物の硬化物)からなる中間体を作製した。
(Preparation of Intermediate of Reference Example 1-B)
Regarding Reference Example 1-B in Table 3 below, the aramid nonwoven fabric was treated in the same manner as in the preparation of the intermediate body of Example 1-A except that an aramid nonwoven fabric (Nomex 410, thickness 50 μm) was used as the fiber. Then, an intermediate body comprising a fixing agent (cured product of epoxy resin composition) was prepared.
(参考例2−Bの中間体の作製)
下記表3中の参考例2−Bについては、繊維として参考例1−Bと同様のアラミド不織布を用いたこと以外は、実施例2−Aの中間体の作製と同様に処理して、アラミド不織布および固着剤(ポリイミド)からなる中間体を作製した。
(Preparation of Intermediate of Reference Example 2-B)
For Reference Example 2-B in Table 3 below, aramid was treated in the same manner as in the preparation of the intermediate of Example 2-A, except that the same aramid nonwoven fabric as in Reference Example 1-B was used as the fiber. An intermediate body made of a non-woven fabric and a fixing agent (polyimide) was prepared.
(参考例3−Bの中間体の作製)
下記表3中の参考例3−Bについては、繊維として参考例1−Bと同様のアラミド不織布を用いたこと以外は、実施例3−Aの中間体の作製と同様に処理して、アラミド不織布および固着剤(ポリイミド)からなる中間体を作製した。
(Preparation of Intermediate of Reference Example 3-B)
For Reference Example 3-B in Table 3 below, aramid was treated in the same manner as in the preparation of the intermediate of Example 3-A, except that the same aramid nonwoven fabric as in Reference Example 1-B was used as the fiber. An intermediate body made of a non-woven fabric and a fixing agent (polyimide) was prepared.
(比較例4−Bの中間体の作製)
参考例1−Bと同様に、上記組成物1を使用してガラスクロスおよび固着剤(エポキシ樹脂組成物の硬化物)からなる中間体を作製した。
(Preparation of Intermediate of Comparative Example 4-B)
In the same manner as in Reference Example 1-B, the above composition 1 was used to prepare an intermediate body composed of a glass cloth and a fixing agent (cured product of epoxy resin composition).
参考例1−B〜3−Bおよび比較例4−Bの各中間体の厚みは53〜56μmであり、アラミド不織布の厚みからの厚みの増大は3〜6μmとわずかだった。 The thickness of each intermediate of Reference Examples 1-B to 3-B and Comparative Example 4-B was 53 to 56 μm, and the increase in thickness from the thickness of the aramid non-woven fabric was slight to 3 to 6 μm.
(各実施例、参考例および比較例の樹脂含有シートないしシートの作製)
実施例1−Aおよび参考例1−Bについては、上記組成物4をプレス機に投入して、140℃で溶融させた後に、上記で得られた各中間体に含浸させ、140℃、3MPa、3分間加熱加圧後、室温まで冷却させることで、固着剤(エポキシ)で固着されたガラスクロスまたはアラミド不織布に、樹脂(高密度ポリエチレン樹脂)が含浸された樹脂含有シートを作製した。
実施例2−A、参考例2−B、実施例3−Aおよび参考例3−Bについては、上記組成物1を、上記で得られた各中間体に対し、繊維全体に行き渡るように適量で塗布し、含浸させ、上記固着剤または樹脂の評価用試験片の作製と同様の条件で、加熱硬化させることで、固着剤(ポリイミド)で固着されたガラスクロスまたはアラミド不織布に樹脂(エポキシ樹脂硬化物)が含浸された樹脂含有シートを作製した。
実施例1−A〜3−Aおよび参考例1−B〜3−Bの各樹脂含有シートの厚みは、中間体の厚みよりも5〜10μm厚くなった。その後、各樹脂含有シートについて、上記と同様の条件で、評価用試験片を作製した。
(Production of Resin-Containing Sheet or Sheet of Each Example, Reference Example and Comparative Example)
For Example 1-A and Reference Example 1-B, the composition 4 was put into a press machine, melted at 140 ° C., and then impregnated into each of the intermediates obtained above, and 140 ° C., 3 MPa. After heating and pressurizing for 3 minutes and then cooling to room temperature, a resin-containing sheet in which a resin (high-density polyethylene resin) was impregnated in a glass cloth or aramid nonwoven fabric fixed with a fixing agent (epoxy) was produced.
For Example 2-A, Reference Example 2-B, Example 3-A and Reference Example 3-B, the composition 1 was added to each intermediate obtained above in an appropriate amount so as to spread over the entire fiber. By applying and impregnating with, and heating and curing under the same conditions as in the preparation of the above-mentioned adhesive or resin evaluation test piece, the glass cloth or aramid non-woven fabric fixed with the adhesive (polyimide) is applied to the resin (epoxy resin). A resin-containing sheet impregnated with a cured product) was produced.
The thickness of each resin-containing sheet of Examples 1-A to 3-A and Reference Examples 1-B to 3-B was 5 to 10 μm thicker than the thickness of the intermediate body. Then, for each resin-containing sheet, an evaluation test piece was prepared under the same conditions as above.
比較例1−Aおよび比較例1−Bについては、上記組成物1を、ガラスクロスまたはアラミド不織布に対し、繊維全体に行き渡るように適量で塗布し、含浸させ、上記固着剤または樹脂の評価用試験片の作製と同様の条件で、加熱硬化させることで、固着剤を含まないガラスクロスまたはアラミド不織布に樹脂(エポキシ樹脂硬化物)が含浸されたシートを作製した。
比較例2−Aおよび比較例2−Bについては、ガラスクロスまたはアラミド不織布に、上記組成物2を比較例1−Aと同様に塗布、含浸させた後、熱風循環式乾燥炉で80℃、30分間の大気条件下で乾燥後、250℃、60分間の大気条件下で加熱してイミド化し、固着剤を含まないガラスクロスまたはアラミド不織布に樹脂(ポリイミド)が含浸されたシートを作製した。
比較例3−Aおよび比較例3−Bについては、上記組成物4をプレス機に投入して、140℃で溶融させた後に、ガラスクロスまたはアラミド不織布に含浸させ、140℃、3MPa、3分間加熱加圧後、室温まで冷却させることで、固着剤を含まないガラスクロスまたはアラミド不織布に樹脂(高密度ポリエチレン樹脂)が含浸されたシートを作製した。
比較例4−Aおよび比較例4−Bについては、比較例2−Aおよび比較例2−Bにおけるガラスクロス又はアラミド不織布を上記組成物1からなる固着剤を有する中間体に変えて使用した以外は、比較例2−A,2−Bと同様に樹脂含有シートを作製した。
その後、各シートについて、上記と同様に評価用試験片を作製した。 For Comparative Example 1-A and Comparative Example 1-B, the composition 1 was applied to a glass cloth or an aramid nonwoven fabric in an appropriate amount so as to spread over the entire fiber, and impregnated with the composition 1 for evaluation of the adhesive or the resin. A sheet was prepared by impregnating a glass cloth or an aramid non-woven fabric containing no fixing agent with a resin (cured product of epoxy resin) by heating and curing under the same conditions as the preparation of the test piece.
For Comparative Example 2-A and Comparative Example 2-B, a glass cloth or an aramid non-woven fabric was coated with and impregnated with the above composition 2 in the same manner as in Comparative Example 1-A, and then 80 ° C. in a hot air circulation drying oven. After drying under atmospheric conditions for 30 minutes, heating at 250 ° C. for 60 minutes under atmospheric conditions to imidize, and a sheet in which a resin (polyimide) was impregnated into a glass cloth or an aramid nonwoven fabric containing no adhesive was produced.
For Comparative Example 3-A and Comparative Example 3-B, the composition 4 was put into a press and melted at 140 ° C., and then impregnated with a glass cloth or an aramid nonwoven fabric, and 140 ° C., 3 MPa, 3 minutes. After heating and pressurizing, cooling to room temperature produced a sheet in which a resin (high-density polyethylene resin) was impregnated in a glass cloth or aramid nonwoven fabric containing no adhesive.
Regarding Comparative Example 4-A and Comparative Example 4-B, except that the glass cloth or aramid non-woven fabric in Comparative Example 2-A and Comparative Example 2-B was used instead of the intermediate having the adhesive agent comprising Composition 1 above. Produced a resin-containing sheet in the same manner as in Comparative Examples 2-A and 2-B.
Then, for each sheet, a test piece for evaluation was prepared in the same manner as above.
なお、樹脂分濃度は、下記表2,表3に示したように、実施例1−A〜3−Aおよび比較例1−A〜4−Aについて同程度であり、また、参考例1−B〜3−Bおよび比較例1−B〜4−Bについても同程度であった。ここで、樹脂分濃度は、固着剤量={1−(繊維基材の体積/中間体の体積)}×100[体積%]、樹脂量={1−(中間体の体積/樹脂含有シートまたはシートの体積)}×100[体積%](体積は、質量および比重を基に換算)から、それぞれ求めた。 In addition, as shown in Tables 2 and 3 below, the resin component concentrations are about the same for Examples 1-A to 3-A and Comparative Examples 1-A to 4-A, and Reference Example 1- The same was true for B to 3-B and Comparative Examples 1-B to 4-B. Here, the resin content concentration is the amount of adhesive = {1- (volume of fiber base material / volume of intermediate)} × 100 [volume%], amount of resin = {1- (volume of intermediate / resin-containing sheet) Or the volume of the sheet) × 100 [volume%] (volume is converted based on mass and specific gravity).
[貯蔵弾性率等の測定]
固着剤または樹脂の貯蔵弾性率等評価用試験片を用いて、DMA粘弾性測定装置((株)日立ハイテクサイエンス製 DMA7100)の引張モードを用い、測定周波数1Hz、最小張力および最小圧縮力200mN、歪振幅10μm、昇温速度5℃/分、大気下条件で粘弾性を測定し、50℃、150℃および250℃における貯蔵弾性率を得るとともに、ガラス転移温度または軟化温度を得た。その結果を下記表1に示す。[Measurement of storage elastic modulus]
Using a test piece for evaluating the storage elastic modulus of the adhesive agent or the resin, using a tensile mode of a DMA viscoelasticity measuring device (manufactured by Hitachi High-Tech Science, DMA7100), a measurement frequency of 1 Hz, a minimum tension and a minimum compression force of 200 mN, The viscoelasticity was measured under atmospheric conditions with a strain amplitude of 10 μm, a temperature rising rate of 5 ° C./minute, and storage elastic moduli at 50 ° C., 150 ° C. and 250 ° C. were obtained, as well as a glass transition temperature or a softening temperature. The results are shown in Table 1 below.
*1:jER828,三菱化学(株)製
*2:2−エチル−4−メチルイミダゾール,四国化成(株)製
*3:和光純薬工業(株)製
*4:比重0.95
* 1: jER828, Mitsubishi Chemical Co., Ltd. * 2: 2-Ethyl-4-methylimidazole, Shikoku Kasei Co., Ltd. * 3: Wako Pure Chemical Industries, Ltd. * 4: Specific gravity 0.95
[樹脂含有シートまたはシートの貯蔵弾性率の評価]
樹脂含有シートまたはシート評価用試験片については、シート中のガラスクロスまたはアラミド不織布の繊維のバイアス(斜め)方向が装置の引張方向となるように試験片を取り付け、最小張力および圧縮力を50mNとした以外は、上記と同様にして粘弾性を測定し、50℃、150℃および250℃における貯蔵弾性率を得た。ここで、バイアス(斜め)方向に測定するのは、繊維基材そのものの弾性率の影響を極力排除し、固着効果による弾性率向上の影響を調べるためである。各実施例および参考例については、固着剤を付着させていない比較例のシートと比べたとき、貯蔵弾性率E[GPa]の値が大きい場合は〇、小さい場合は×とした。
[Evaluation of storage elastic modulus of resin-containing sheet or sheet]
For the resin-containing sheet or the test piece for sheet evaluation, the test piece was attached so that the bias (oblique) direction of the fiber of the glass cloth or aramid nonwoven fabric in the sheet was the tensile direction of the device, and the minimum tension and compression force were 50 mN. The viscoelasticity was measured in the same manner as above except that the storage elastic moduli at 50 ° C., 150 ° C. and 250 ° C. were obtained. Here, the measurement in the bias (oblique) direction is to eliminate the influence of the elastic modulus of the fiber base material as much as possible and to investigate the influence of the elastic modulus improvement due to the sticking effect. In each of the Examples and Reference Examples, when the storage elastic modulus E [GPa] has a large value when compared with the sheet of the Comparative Example to which the adhesive is not attached, the value is ◯, and when the value is small, the value is x.
具体的に説明すると、実施例1−Aの樹脂含有シートは、50℃、150℃、250℃のいずれの温度においても、固着剤を使用しなかった比較例3−Aのシートよりも貯蔵弾性率E[GPa]の値が大きいため、「〇」とした。
参考例1−Bにおいても、固着剤を使用しなかった比較例3−Bのシートと比較して貯蔵弾性率E[GPa]の値が大きいため、「〇」とした。
実施例2−A,参考例2−B,実施例3−A,参考例3−Bの樹脂含有シートにおいても、それぞれ固着剤を使用しなかった比較例1−A,1−Bのシートと比較して貯蔵弾性率E[GPa]の値が大きいため、「〇」とした。
一方、比較例4−Aの樹脂含有シートは、50℃、150℃、250℃のいずれの温度においても、固着剤を使用しなかった比較例2−Aのシートよりも貯蔵弾性率E[GPa]の値が小さくなるため、「×」とした。
比較例4−Bの樹脂含有シートにおいても、固着剤を使用しなかった比較例2−Bのシートと比較して「×」とした。
その結果を下記表2、表3に示す。
More specifically, the resin-containing sheet of Example 1-A has a storage elastic modulus at any temperature of 50 ° C., 150 ° C., and 250 ° C. more than that of the sheet of Comparative Example 3-A in which no adhesive was used. Since the value of the rate E [GPa] is large, it was set to “◯”.
Also in Reference Example 1-B, the value of the storage elastic modulus E [GPa] was larger than that of the sheet of Comparative Example 3-B in which no fixing agent was used, and thus was set to “◯”.
Also in the resin-containing sheets of Example 2-A, Reference Example 2-B, Example 3-A, and Reference Example 3-B, the sheets of Comparative Examples 1-A and 1-B in which no adhesive was used were used. Since the value of the storage elastic modulus E [GPa] is large in comparison, it was set to “◯”.
On the other hand, the resin-containing sheet of Comparative Example 4-A has a storage elastic modulus E [GPa at any temperature of 50 ° C., 150 ° C., and 250 ° C. as compared with the sheet of Comparative Example 2-A in which no adhesive was used. Since the value of], becomes small, it was set as “x”.
Also in the resin-containing sheet of Comparative Example 4-B, "x" was given as compared with the sheet of Comparative Example 2-B in which no fixing agent was used.
The results are shown in Tables 2 and 3 below.
なお、参考として、ガラスクロスのみを用いて上記測定を実施した場合、バイアス方向の引張りにより測定開始時において編み込んだ繊維がほどけたために、貯蔵弾性率の値が得られなかった。 As a reference, when the above measurement was performed using only glass cloth, the value of the storage elastic modulus could not be obtained because the fiber knitted at the start of the measurement was unraveled by the tension in the bias direction.
[密着性評価用試験片の作製]
繊維基材としてのガラスクロスまたはアラミド不織布をキャリアフィルム上に配置したこと以外は、上記と同様にして固着剤組成物を塗布、含浸させて、各中間体を作製した。その後、乾燥後の固着剤の表面に、樹脂組成物を成形または塗布し、乾燥させた後、カバーフィルムを貼り合わせて、ドライフィルムを得た。このドライフィルムの両面に厚み18μmの表面未処理銅箔を重ね合わせて(密着させる際にキャリアフィルムおよびカバーフィルムは剥離した)、真空プレス機で、加圧条件を1MPa、加熱条件を、実施例1−Aおよび参考例1−Bについては150℃×10分、実施例2−Aおよび参考例2−B,比較例4−Aおよび4−Bについては250℃×60分、実施例3−Aおよび参考例3−Bについては300℃×60分として成形し、樹脂層と銅箔とが密着した密着性評価用試験片を作製した。また、比較例1−A〜3−A,比較例1−B〜3−Bについては、固着剤組成物を塗布、含浸しないこと以外は同様にドライフィルムを作製、真空プレス機で加圧し、比較例1−A〜3−Aおよび比較例1−B〜3−Bのシート作製と同様の温度条件で密着性評価用試験片を作製した。
[Preparation of test piece for adhesion evaluation]
The adhesive composition was applied and impregnated in the same manner as above except that the glass cloth or the aramid non-woven fabric as the fiber base material was placed on the carrier film to produce each intermediate. After that, the resin composition was molded or applied on the surface of the dried adhesive, dried, and then a cover film was attached to obtain a dry film. A surface-untreated copper foil having a thickness of 18 μm was superposed on both sides of this dry film (the carrier film and the cover film were peeled off when they were brought into close contact), and the pressurizing condition was 1 MPa and the heating condition was 150 ° C. × 10 minutes for 1-A and Reference Example 1-B, 250 ° C. × 60 minutes for Example 2-A and Reference Example 2-B, Comparative Examples 4-A and 4-B, Example 3- About A and Reference Example 3-B, it shape | molded at 300 degreeC x 60 minutes, and produced the adhesiveness evaluation test piece which the resin layer and the copper foil adhered. Further, for Comparative Examples 1-A to 3-A and Comparative Examples 1-B to 3-B, dry films were prepared in the same manner except that the adhesive composition was not applied and impregnated, and pressed with a vacuum press, Adhesion evaluation test pieces were prepared under the same temperature conditions as the sheet preparation of Comparative Examples 1-A to 3-A and Comparative Examples 1-B to 3-B.
[密着性の評価]
密着性評価用試験片を用いて、樹脂層と表面未処理銅箔との界面で両者を剥離する際のピール強度を、ピール角度90°、ピール速度50mm/分として測定し、0.5kN/m以上の場合を〇、0.5kN/m未満の場合を×とした。その結果を下記表2、表3に示す。ピール強度が高い場合、凹凸に追従する密着性に優れ、銅箔との密着性に優れるといえる。[Evaluation of adhesion]
Using the test piece for adhesion evaluation, the peel strength at the time of peeling the resin layer and the surface untreated copper foil at the interface was measured at a peel angle of 90 ° and a peel speed of 50 mm / min. The case of m or more was ◯, and the case of less than 0.5 kN / m was x. The results are shown in Tables 2 and 3 below. It can be said that when the peel strength is high, the adhesion to follow unevenness is excellent and the adhesion to the copper foil is excellent.
上記表2,3に示すように、実施例1−A〜3−A,参考例1−B〜3−Bの固着剤の貯蔵弾性率は、樹脂の貯蔵弾性率に比べていずれも大きく、一方、比較例4−A,4−Bでは、固着剤の貯蔵弾性率が樹脂の貯蔵弾性率に比べ、いずれも小さくなっている。また、比較例1−A〜3−A,1−B〜3−Bでは、樹脂のみを用いて、固着剤を用いていない。 As shown in Tables 2 and 3 above, the storage elastic moduli of the adhesives of Examples 1-A to 3-A and Reference Examples 1-B to 3-B are all larger than the storage elastic moduli of the resins, On the other hand, in Comparative Examples 4-A and 4-B, the storage elastic modulus of the adhesive agent is smaller than the storage elastic modulus of the resin. Further, in Comparative Examples 1-A to 3-A and 1-B to 3-B, only the resin was used and the adhesive was not used.
上記表2,3に示す通り、固着剤の貯蔵弾性率が樹脂の貯蔵弾性率よりも高い固着剤を用いて、ガラスクロスまたはアラミド不織布を固着し、さらに樹脂を含浸させた実施例および参考例の樹脂含有シートは、樹脂のみを含浸させた比較例のシートと比べ、密着性に優れており、かつ、貯蔵弾性率が大きいことがわかる。
例えば、実施例1−Aと比較例3−Aとを対比すると明らかなように、ガラスクロスの繊維同士を固着組成物により固着させ、さらに繊維基材に樹脂組成物を含浸させた実施例の樹脂含有シートは、ガラスクロスの繊維同士を固着組成物により固着させていない比較例3−Aと比較して、いずれの温度においても貯蔵弾性率が高いので、力学強度が高いことが分かった。
特に、実施例2−A,3−Aおよび参考例2−B,3−Bの樹脂含有シートは、250℃の貯蔵弾性率が1GPaを超えており、高温時の力学強度にも優れていることがわかる。一方、固着剤の貯蔵弾性率が樹脂の貯蔵弾性率よりも低い比較例4−Aおよび比較例4−Bでは、樹脂含有シートとしての貯蔵弾性率が低くなり、密着性も劣っていた。
As shown in Tables 2 and 3 above, Examples and Reference Examples in which a glass cloth or an aramid non-woven fabric was fixed using a fixing agent having a storage elastic modulus of the fixing agent higher than that of the resin, and further impregnated with the resin. It can be seen that the resin-containing sheet of No. 2 has excellent adhesiveness and a large storage elastic modulus as compared with the sheet of Comparative Example in which only the resin is impregnated.
For example, as is clear from comparison between Example 1-A and Comparative Example 3-A, the fibers of the glass cloth were fixed to each other by the fixing composition, and the fiber base material was impregnated with the resin composition. It was found that the resin-containing sheet has high storage strength at any temperature as compared with Comparative Example 3-A in which the fibers of the glass cloth are not fixed by the fixing composition, and thus has high mechanical strength.
In particular, the resin-containing sheets of Examples 2-A, 3-A and Reference Examples 2-B, 3-B have a storage elastic modulus at 250 ° C of more than 1 GPa and are also excellent in mechanical strength at high temperature. I understand. On the other hand, in Comparative Example 4-A and Comparative Example 4-B in which the storage elastic modulus of the adhesive is lower than the storage elastic modulus of the resin, the storage elastic modulus as the resin-containing sheet was low and the adhesion was also poor.
以上より、繊維基材中の繊維同士を固着する固着剤と、固着された繊維に接する樹脂とを有し、固着剤の貯蔵弾性率が樹脂の貯蔵弾性率よりも高い樹脂含有シートを用いることにより、優れた力学強度、弾性率および密着性を実現することが可能であることが確かめられた。かかる本発明の樹脂含有シートは、電子機器用の配線板等に適用することができ、例えば、配線板用の層間絶縁材やソルダーレジスト、コア材等に好適に適用することができる。 From the above, using a resin-containing sheet having a fixing agent for fixing the fibers in the fiber base material and a resin in contact with the fixed fibers, and the storage elastic modulus of the fixing agent is higher than the storage elastic modulus of the resin. It was confirmed that it is possible to realize excellent mechanical strength, elastic modulus and adhesion. The resin-containing sheet of the present invention can be applied to a wiring board for electronic devices and the like, and can be suitably applied to, for example, an interlayer insulating material for wiring boards, a solder resist, and a core material.
1,21 繊維
2 固着剤
3 樹脂
11 繊維基材
P 接点
D 張力Tにより繊維が引き離される方向
S 空間1, 21 fiber 2 adhesive 3
Claims (6)
前記繊維基材中の繊維同士を固着する固着剤と、
前記繊維基材と固着剤とに接する樹脂と、を有し、
前記固着剤の貯蔵弾性率が、前記樹脂の貯蔵弾性率よりも高いことを特徴とする樹脂含有シート。 Fiber substrate different from wholly aromatic polyamide fiber,
A fixing agent for fixing the fibers in the fiber base material to each other,
A resin in contact with the fiber base material and the adhesive,
A resin-containing sheet, wherein the storage elastic modulus of the adhesive is higher than the storage elastic modulus of the resin.
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