JP5846290B2 - ハロゲンフリー難燃性接着剤組成物 - Google Patents
ハロゲンフリー難燃性接着剤組成物 Download PDFInfo
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- JP5846290B2 JP5846290B2 JP2014503760A JP2014503760A JP5846290B2 JP 5846290 B2 JP5846290 B2 JP 5846290B2 JP 2014503760 A JP2014503760 A JP 2014503760A JP 2014503760 A JP2014503760 A JP 2014503760A JP 5846290 B2 JP5846290 B2 JP 5846290B2
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- resin
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- flame retardant
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- 239000000203 mixture Substances 0.000 title claims description 82
- 239000000853 adhesive Substances 0.000 title claims description 76
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- 239000003063 flame retardant Substances 0.000 title claims description 65
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 title description 8
- 229920006122 polyamide resin Polymers 0.000 claims description 62
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 54
- 239000010408 film Substances 0.000 claims description 46
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- 239000013034 phenoxy resin Substances 0.000 claims description 43
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- 239000012790 adhesive layer Substances 0.000 claims description 35
- 229920001721 polyimide Polymers 0.000 claims description 30
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 25
- 239000012787 coverlay film Substances 0.000 claims description 21
- 229910052698 phosphorus Inorganic materials 0.000 claims description 17
- 239000011889 copper foil Substances 0.000 claims description 16
- 239000011574 phosphorus Substances 0.000 claims description 16
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 13
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- 125000005843 halogen group Chemical group 0.000 claims description 9
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- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
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- 229910052732 germanium Inorganic materials 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 229910052748 manganese Inorganic materials 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 229910052712 strontium Inorganic materials 0.000 claims description 3
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- 238000004519 manufacturing process Methods 0.000 description 11
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- 238000006243 chemical reaction Methods 0.000 description 9
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
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- 230000000052 comparative effect Effects 0.000 description 7
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- 238000000034 method Methods 0.000 description 7
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229920000877 Melamine resin Polymers 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 229920000388 Polyphosphate Polymers 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
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- 125000003277 amino group Chemical group 0.000 description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 125000004437 phosphorous atom Chemical group 0.000 description 4
- 239000001205 polyphosphate Substances 0.000 description 4
- 235000011176 polyphosphates Nutrition 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 229920005992 thermoplastic resin Polymers 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- SSUJUUNLZQVZMO-UHFFFAOYSA-N 1,2,3,4,8,9,10,10a-octahydropyrimido[1,2-a]azepine Chemical compound C1CCC=CN2CCCNC21 SSUJUUNLZQVZMO-UHFFFAOYSA-N 0.000 description 3
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical group C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 3
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- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical class CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 2
- PBLZLIFKVPJDCO-UHFFFAOYSA-N 12-aminododecanoic acid Chemical compound NCCCCCCCCCCCC(O)=O PBLZLIFKVPJDCO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical group C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- LTQBNYCMVZQRSD-UHFFFAOYSA-N (4-ethenylphenyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1=CC=C(C=C)C=C1 LTQBNYCMVZQRSD-UHFFFAOYSA-N 0.000 description 1
- RUEBPOOTFCZRBC-UHFFFAOYSA-N (5-methyl-2-phenyl-1h-imidazol-4-yl)methanol Chemical compound OCC1=C(C)NC(C=2C=CC=CC=2)=N1 RUEBPOOTFCZRBC-UHFFFAOYSA-N 0.000 description 1
- MEBONNVPKOBPEA-UHFFFAOYSA-N 1,1,2-trimethylcyclohexane Chemical group CC1CCCCC1(C)C MEBONNVPKOBPEA-UHFFFAOYSA-N 0.000 description 1
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
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- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- PJEUXMXPJGWZOZ-UHFFFAOYSA-L zinc;diphenylphosphinate Chemical compound [Zn+2].C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1.C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1 PJEUXMXPJGWZOZ-UHFFFAOYSA-L 0.000 description 1
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Classifications
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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- C09J177/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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-
- C—CHEMISTRY; METALLURGY
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- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/35—Heat-activated
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/38—Improvement of the adhesion between the insulating substrate and the metal
- H05K3/386—Improvement of the adhesion between the insulating substrate and the metal by the use of an organic polymeric bonding layer, e.g. adhesive
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Description
本明細書において、「接着性層」は、ポリアミド樹脂(A)、フェノキシ樹脂(B)、エポキシ樹脂(C)及びリン系難燃剤(D)を含む膜等の部分において、少なくとも一部が硬化し始めた段階で、被着体への接着、又は、同一材料若しくは異なる材料からなる少なくとも2つの部材どうしの接着を可能としている性質を有する層を意味する。また、「接着部」は、接着後に形成された硬化物からなる硬化部を意味し、「硬化物」は、完全硬化のみを意味するものでなく、半硬化等、少なくとも一部に架橋構造を有する状態を含む。
1.(A)25℃で固体の溶剤可溶性ポリアミド樹脂、(B)フェノキシ樹脂、(C)ハロゲン原子を含まないエポキシ樹脂、及び(D)下記一般式(1)で示される構造を有するリン系難燃剤を含有し、上記フェノキシ樹脂(B)の含有量は、上記ポリアミド樹脂(A)100質量部に対して50〜500質量部であり、上記エポキシ樹脂(C)の含有量は、上記ポリアミド樹脂(A)及び上記フェノキシ樹脂(B)の合計100質量部に対して1〜60質量部であり、上記リン系難燃剤(D)の含有量は、上記ポリアミド樹脂(A)及び上記フェノキシ樹脂(B)の合計100質量部に対して5〜100質量部であることを特徴とするハロゲンフリー難燃性接着剤組成物。
2.上記エポキシ樹脂(C)が、1分子中に3個以上のエポキシ基を有する上記1に記載のハロゲンフリー難燃性接着剤組成物。
3.熱硬化により得られた硬化物のガラス転移温度が80℃以上である上記1又は2に記載のハロゲンフリー難燃性接着剤組成物。
4.上記1〜3のいずれかに記載の接着剤組成物を用いて得られた接着性層が、ポリイミドフィルムの一方の表面に形成されてなることを特徴とするカバーレイフィルム。
5.上記1〜3のいずれかに記載の接着剤組成物を用いて、ポリイミドフィルムの少なくとも一方の表面に銅箔を貼り合わせてなることを特徴とするフレキシブル銅張積層板。
6.上記1〜3のいずれかに記載の接着剤組成物を用いて得られた接着性層が、離型性フィルムの一方の表面に形成されてなることを特徴とするボンディングシート。
本発明のハロゲンフリー難燃性接着剤組成物(以下、単に「接着剤組成物」ともいう)は、(A)25℃で固体の溶剤可溶性ポリアミド樹脂、(B)フェノキシ樹脂、(C)ハロゲン原子を含まないエポキシ樹脂、及び、(D)特定の構造を有するリン系難燃剤を、所定量含有する組成物である。
以下、本発明の接着剤組成物に含まれる成分について、具体的に説明する。
このポリアミド樹脂(A)は、本発明の接着剤組成物の主要な成分の1つであり、接着性や硬化物の柔軟性等を与える成分である。ポリアミド樹脂(A)は、25℃で固体であり、後述する有機溶剤に可溶な樹脂であれば、特に限定されず、具体例としては、二塩基酸及びジアミンを共重縮合して得られる共重合ポリアミド樹脂、分子中のアミド結合にN−アルコキシメチル基を導入した変性ポリアミド樹脂等が挙げられる。
このフェノキシ樹脂(B)は、接着性、及び、接着部における耐熱性を向上させる効果がある。フェノキシ樹脂(B)は、特に限定されず、ビスフェノールA骨格、ビスフェノールF骨格、ビスフェノールS骨格、ビスフェノールアセトフェノン骨格、ノボラック骨格、ビフェニル骨格、フルオレン骨格、ジシクロペンタジエン骨格、ノルボルネン骨格、ナフタレン骨格、アントラセン骨格、アダマンタン骨格、テルペン骨格、トリメチルシクロヘキサン骨格から選択される1種以上の骨格を有する樹脂が好ましく用いられる。上記フェノキシ樹脂(B)の具体例としては、ビスフェノールA型フェノキシ樹脂、ビスフェノールF型フェノキシ樹脂、ビスフェノールS型フェノキシ樹脂、リン系フェノキシ樹脂等が挙げられる。尚、上記フェノキシ樹脂(B)の末端構造は、特に限定されず、ヒドロキシル基、グリシジル基等とすることができる。また、分子量も特に限定されないが、好ましい重量平均分子量(Mw)は30000〜100000である。Mwがこの範囲内であれば、被着体への接着性が良好であり、耐熱性にも優れる。上記フェノキシ樹脂(B)は、単独で用いてよいし、2種以上を組み合わせて用いてもよい。
このエポキシ樹脂(C)は、接着性や接着後の硬化部における耐熱性等を与える成分である。従来、ハロゲン原子を含むエポキシ樹脂は、接着性に優れた接着剤組成物の原料成分として知られているが、本発明においては、ハロゲン原子を含まないエポキシ樹脂(C)を用いて、上記の効果を得ることができる。そして、廃棄後の環境汚染を抑制することができる。
上記エポキシ樹脂(C)としては、例えば、オルトフタル酸ジグリシジルエステル、イソフタル酸ジグリシジルエステル、テレフタル酸ジグリシジルエステル、p−ヒドロキシ安息香酸ジグリシジルエステル、テトラヒドロフタル酸ジグリシジルエステル、コハク酸ジグリシジルエステル、アジピン酸ジグリシジルエステル、セバシン酸ジグリシジルエステル、トリメリット酸トリグリシジルエステル等のグリシジルエステル;ビスフェノールAのジグリシジルエーテル及びそのオリゴマー、エチレングリコールジグリシジルエーテル、プロピレングリコールジグリシジルエーテル、1,4−ブタンジオール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、トリメチロールプロパントリグリシジルエーテル、ペンタエリスリトールテトラグリシジルエーテル、テトラフェニルグリシジルエーテルエタン、トリフェニルグリシジルエーテルエタン、ソルビトールのポリグリシジルエーテル、ポリグリセロールのポリグリシジルエーテル等のグリシジルエーテル類;フェノールノボラックエポキシ樹脂、o−クレゾールノボラックエポキシ樹脂、ビスフェノールAノボラックエポキシ樹脂等のノボラック型エポキシ樹脂等が挙げられる。これらのエポキシ樹脂は、単独で用いてよいし、2種以上を組み合わせて用いてもよい。
1分子中に3個以上のエポキシ基を有する化合物を含む場合、上記エポキシ樹脂(C)の全体に対する割合の下限は、好ましくは15質量%、より好ましくは20質量%、更に好ましくは25質量%である。
この難燃剤(D)は、下記一般式(1)で示される含リン化合物である。この含リン化合物は、単独で用いてよいし、2種以上を組み合わせて用いてもよい。
本発明のカバーレイフィルムは、上記本発明の接着剤組成物を用いて得られた接着性層が、ポリイミドフィルムの一方の表面に形成されていることを特徴とする。上記本発明の接着剤組成物は、ポリイミド系樹脂との接着性に優れるので、本発明のカバーレイフィルムは、接着性層及びポリイミドフィルムの剥離が困難なフィルムである。
上記ポリイミドフィルムの厚さは、通常、10〜125μmである。
また、上記接着性層の厚さは、通常、5〜45μmであり、好ましくは10〜35μmである。
本発明のフレキシブル銅張積層板は、上記本発明の接着剤組成物を用いて、ポリイミドフィルムと銅箔とが貼り合わされていることを特徴とする。即ち、本発明のフレキシブル銅張積層板は、ポリイミドフィルム、接着性組成物により形成された接着層及び銅箔の順に構成されたものである。尚、接着層及び銅箔は、ポリイミドフィルムの両面に形成されていてもよい。上記本発明の接着剤組成物は、銅を含む物品との接着性に優れるので、本発明のフレキシブル銅張積層板は、一体化物として安定性に優れる。
上記接着層は、上記成分(A)、(B)及び(C)の大部分が架橋反応して硬化物を形成していることが好ましい。
上記接着層の厚さは、通常、5〜45μmであり、好ましくは5〜18μmである。
また、上記銅箔は、特に限定されず、電解銅箔、圧延銅箔等を用いることができる。
本発明のボンディングシートは、上記本発明の接着剤組成物を用いて得られた接着性層が、離型性フィルムの表面に形成されていることを特徴とする。尚、本発明のボンディングシートは、2枚の離型性フィルムの間に接着性層を備える態様であってもよい。
上記離型性フィルムの厚さは、通常、20〜100μmである。
また、上記接着性層の厚さは、通常、5〜50μmであり、好ましくは10〜35μmである。
(1)熱硬化後の硬化物のガラス転移温度
厚さ38μmの離型処理されたPETフィルムを用意し、その表面に、表1に記載の液状接着剤組成物を、ロ−ル塗布した。次いで、この塗膜付きフィルムをオーブン内に静置して、140℃で2分間乾燥させて厚さ25μmの被膜を得た。その後、更にオーブンにて160℃で2時間のアフターキュアを行った。
次に、得られた積層フィルムから、PETフィルムを剥がして、硬化膜を得て、これをガラス転移温度測定用の試験片とした。この試験片を、動的粘弾性測定装置「EXSTAR DMS6100」(エスアイアイ・ナノテクノロジー社製)により、昇温速度2℃/分、周波数10Hzの条件にて、引張りモードで測定に供した。得られた曲線の損失正接の最大値をガラス転移温度とした。
厚さ25μmポリイミドフィルムを用意し、その表面に、表1に記載の液状接着剤組成物を、ロ−ル塗布した。次いで、この塗膜付きフィルムをオーブン内に静置して、140℃で2分間乾燥させて厚さ25μmの被膜(接着性層)を形成し、カバーレイフィルムを得た。その後、厚さ35μmの圧延銅箔を、カバーレイフィルムの接着性層の表面に面接触するように重ね合わせ、150℃、圧力0.3MPa、及び速度1m/分の条件でラミネ−トを行った。次いで、この積層体(ポリイミドフィルム/接着性層/銅箔)を150℃、及び圧力3MPaの条件で5分間加熱圧着した後、更にオ−ブンにて160℃で2時間のアフタ−キュアを行うことにより、フレキシブル銅張積層板を得た。このフレキシブル銅張積層板を加工して、所定の大きさの接着試験片を作製した。
接着性を評価するために、JIS C 6481に準拠し、23℃及び引張速度50mm/分の条件で、接着試験片のポリイミドフィルムを銅箔から剥がすときのはく離接着強さ(N/mm)を測定した。測定時の接着試験片の幅は10mmとした。
また、耐熱性を評価するために、JIS C 6481に準拠し、下記の方法ではんだ耐熱性試験を行った。
フレキシブル銅張積層板におけるポリイミドフィルムの面を上側にして、上記接着試験片を260℃のはんだ浴に60秒間浮かべ、接着層の膨れ、銅箔の剥がれ等の有無を目視により観察した。そして、耐熱性を下記基準で判定した。
1:膨れ及び剥がれは認められなかった
2:膨れ又は剥がれが認められた
上記カバーレイフィルムをオーブン内に静置して、160℃で2時間加熱を行うことにより、被膜(接着性層)を硬化させ、硬化フィルムを得た。この硬化フィルムを用いて、UL−94に準拠して難燃性の試験を行った。そして、難燃性を下記基準で判定した。
1:VTM−0に合格
2:VTM−0に不合格
上記カバーレイフィルムをオーブン内に静置して、160℃で2時間加熱を行うことにより、被膜(接着性層)を硬化させ、硬化フィルムを得た。この硬化フィルムの接着層を、ガラスに密着させ、指で押圧し、その後、剥離したときのガラスへの付着物の有無を目視で観察した。そして、ブリードアウトを下記基準で判定した。
1:ガラスに付着物がなかった
2:ガラスに付着物があった
くし型テストパターン(線幅100μm、線間100μm)を有する基板の全表面に、上記カバーレイフィルムにおける被膜(接着性層)を面接触させ、オーブン内にて、150℃、及び圧力3MPaの条件で5分間加熱圧着した後に、更にオーブンにて160℃で2時間のアフターキュアを行い、絶縁信頼性用の試験片とした。この試験片を、温度85℃、湿度85%の雰囲気中、直流電圧50Vを、1000時間印加した。その後、パターン間の抵抗値を測定し、絶縁信頼性を下記基準で判定した。抵抗値が107Ω以上であれば、実用上、十分な絶縁信頼性が得られていると判断できる。
1:抵抗値が107Ω以上であった
2:抵抗値が107Ω未満であった
2−1.ポリアミド樹脂(A)
(1)ポリアミド樹脂a1
攪拌機、還流脱水装置及び蒸留管を備えたフラスコに、アゼライン酸65部、ドデカン二酸190部、ピペラジン100部及び蒸留水120部を仕込んだ。次いで、反応系の温度を120℃に昇温して水を留出させた後に、20℃/時間の割合で240℃にまで昇温し、240℃で3時間反応を継続してポリアミド樹脂a1を得た。
ポリアミド樹脂a1は、25℃で固体である。アミン価は4.5mgKOH/gである。このポリアミド樹脂a1は、メタノール等の溶剤に可溶である。
(2)ポリアミド樹脂a2
ポリアミド樹脂「TPAE−826−5A」(商品名、T&K TOKA社製)を用いた。
ポリアミド樹脂a2は、25℃で固体である。アミン価は5.0mgKOH/gである。このポリアミド樹脂a2は、メタノール等の溶剤に可溶である。
(1)フェノキシ樹脂b1
フェノキシ樹脂「jer1256」(商品名、三菱化学社製)を用いた。
(2)フェノキシ樹脂b2
フェノキシ樹脂「jerYX−8100BH30」(商品名、三菱化学社製)を用いた。
(1)エポキシ樹脂c1
クレゾールノボラック型多官能エポキシ樹脂「エポトートYDCN−701」(商品名、新日鐵化学社製)を用いた。
(2)エポキシ樹脂c2
変性ノボラック型多官能エポキシ樹脂「EPICLON N−865」(商品名、DIC社製)を用いた。
(1)難燃剤d1
トリスジエチルホスフィン酸アルミニウム「エクソリットOP−935」(商品名、クラリアントジャパン社製)を用いた。この難燃剤d1は、下記混合溶剤に不溶である。
(2)難燃剤x
シクロホスファゼンオリゴマー「SPB−100」(商品名、大塚化学社製)を用いた。この難燃剤xは、下記混合溶剤に可溶である。
(1)硬化剤e1
ノボラック型フェノール樹脂「フェノライトLA−1356」(商品名、DIC社製)を用いた。
(2)硬化剤e2
2,4−ジアミノ−6−[2’−メチルイミダゾリル−(1’)]−エチル−s−トリアジン「キュアゾール2MZ−A」(商品名、四国化成社製)を用いた。
(3)硬化剤e3
1,8−ジアザビシクロ[5.4.0]ウンデセンのオクチル酸塩「U−CAT SA−102」(商品名、サンアプロ社製)を用いた。
実施例1〜5及び比較例1〜6
難燃剤(D)を除く上記の原料を、表1に示す割合で用い、トルエン、メタノ−ル及びメチルエチルケトンからなる混合溶剤(質量比=25:25:50)に添加し、攪拌溶解することにより、均一溶液を得た。次いで、所定量の難燃剤(D)を添加し、固形分濃度30%の液状接着剤組成物を調製した。尚、上記のように、難燃剤d1は、混合溶剤に不溶であるので、難燃剤d1を含む組成物は分散液である。一方、難燃剤xは、混合溶剤に可溶であるので、難燃剤xを含む組成物は溶液である。
その後、液状接着剤組成物を用いて、上記の各種評価を行った。その結果を表1に示す。尚、表1には、上記原料(A)、(B)、(C)及び(D)の合計量に対する、難燃剤(D)に由来するリン原子の含有率も併せて示した。
Claims (5)
- (A)25℃で固体の溶剤可溶性ポリアミド樹脂、(B)フェノキシ樹脂、(C)ハロゲン原子を含まないエポキシ樹脂、及び(D)下記一般式(1)で示される構造を有するリン系難燃剤を含有し、
前記エポキシ樹脂(C)は、1分子中に3個以上のエポキシ基を有するエポキシ樹脂であり、
前記フェノキシ樹脂(B)の含有量は、前記ポリアミド樹脂(A)100質量部に対して100〜450質量部であり、前記エポキシ樹脂(C)の含有量は、前記ポリアミド樹脂(A)及び前記フェノキシ樹脂(B)の合計100質量部に対して1〜60質量部であり、前記リン系難燃剤(D)の含有量は、前記ポリアミド樹脂(A)及び前記フェノキシ樹脂(B)の合計100質量部に対して5〜100質量部であることを特徴とするハロゲンフリー難燃性接着剤組成物。
- 熱硬化により得られた硬化物のガラス転移温度が80℃以上である請求項1に記載のハロゲンフリー難燃性接着剤組成物。
- 請求項1又は2に記載の接着剤組成物を用いて得られた接着性層が、ポリイミドフィルムの一方の表面に形成されてなることを特徴とするカバーレイフィルム。
- 請求項1又は2に記載の接着剤組成物を用いて、ポリイミドフィルムの少なくとも一方の表面に銅箔を貼り合わせてなることを特徴とするフレキシブル銅張積層板。
- 請求項1又は2に記載の接着剤組成物を用いて得られた接着性層が、離型性フィルムの一方の表面に形成されてなることを特徴とするボンディングシート。
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