JP6330892B2 - マレイミド樹脂組成物、その硬化物、プリプレグ、積層板及び多層プリント配線板 - Google Patents
マレイミド樹脂組成物、その硬化物、プリプレグ、積層板及び多層プリント配線板 Download PDFInfo
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- JP6330892B2 JP6330892B2 JP2016233097A JP2016233097A JP6330892B2 JP 6330892 B2 JP6330892 B2 JP 6330892B2 JP 2016233097 A JP2016233097 A JP 2016233097A JP 2016233097 A JP2016233097 A JP 2016233097A JP 6330892 B2 JP6330892 B2 JP 6330892B2
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- 229920006287 phenoxy resin Polymers 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920002627 poly(phosphazenes) Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- MIROPXUFDXCYLG-UHFFFAOYSA-N pyridine-2,5-diamine Chemical compound NC1=CC=C(N)N=C1 MIROPXUFDXCYLG-UHFFFAOYSA-N 0.000 description 1
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000790 scattering method Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000003384 small molecules Chemical group 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- LTURHSAEWJPFAA-UHFFFAOYSA-N sulfuric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OS(O)(=O)=O.NC1=NC(N)=NC(N)=N1 LTURHSAEWJPFAA-UHFFFAOYSA-N 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical compound N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-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
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- C08G73/02—Polyamines
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
- C08G73/125—Unsaturated polyimide precursors the unsaturated precursors containing atoms other than carbon, hydrogen, oxygen or nitrogen in the main chain
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- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
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- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
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- 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
- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
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- 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
- C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
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- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08L79/085—Unsaturated polyimide precursors
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- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
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- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
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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
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/032—Organic insulating material consisting of one material
- H05K1/0346—Organic insulating material consisting of one material containing N
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- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
- H05K2201/01—Dielectrics
- H05K2201/0137—Materials
- H05K2201/0162—Silicon containing polymer, e.g. silicone
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- 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
- H05K3/389—Improvement of the adhesion between the insulating substrate and the metal by the use of a coupling agent, e.g. silane
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- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Description
また、高密度実装、高多層化積層板に広く使用されているポリビスマレイミド樹脂は、その耐熱性は非常に優れているものの、吸湿性が高く、接着性に難点がある。さらに、積層時にエポキシ樹脂に比べ高温、長時間を必要とし生産性が悪いという欠点もある。
1.(A)下記一般式(1)に示すシロキサンジアミン、(B)分子構中に少なくとも2個のN−置換マレイミド基を有するマレイミド化合物、(C)下記一般式(2)に示す酸性置換基を有するアミン化合物を反応させることを特徴とする変性シリコーン化合物の製造方法。
[式(1)中、複数のR1は、それぞれ独立にアルキル基、フェニル基又は置換フェニル基を示し、互いに同じでも異なっていても良く、複数のR2は、それぞれ独立にアルキル基、フェニル基又は置換フェニル基を示し、互いに同じでも異なっていても良く、R3及びR4はそれぞれ独立にアルキル基、フェニル基又は置換フェニル基を示し、R5及びR6はそれぞれ独立に2価の有機基を示し、nは2〜50の整数を示す。]
[式(2)中、R9は複数ある場合は各々独立に、酸性置換基である水酸基、カルボキシル基又はスルホン酸基を示し、R10は複数ある場合は各々独立に水素原子、炭素数1〜5の脂肪族炭化水素基、ハロゲン原子を示し、xは1〜5の整数、yは0〜4の整数で、x+y=5である。]
3.上記1又は2に記載の変性シリコーン化合物の製造方法により変性シリコーン化合物を製造する工程を含むことを特徴とする熱硬化性樹脂組成物の製造方法。
4.前記変性シリコーン化合物を製造する工程により製造された変性シリコーン化合物にエポキシ樹脂および/又はシアネート樹脂を含有させることを特徴とする上記3に記載の熱硬化性樹脂組成物の製造方法。
5.前記変性シリコーン化合物を製造する工程により製造された変性シリコーン化合物に無機充填剤を含有させることを特徴とする上記3又は4に記載の熱硬化性樹脂組成物の製造方法。
6.上記3〜5いずれかの熱硬化性樹脂組成物の製造方法により熱硬化性樹脂組成物を製造する工程を含み、前記熱硬化性樹脂組成物を製造する工程で製造された熱硬化性樹脂組成物を用いることを特徴とするプリプレグの製造方法。
7.上記6のプリプレグの製造方法によりプリプレグを製造する工程を含み、前記プリプレグを製造する工程により製造されたプリプレグを積層成形することを特徴とする積層板の製造方法。
8.上記7の積層板の製造方法により積層板を製造する工程を含み、前記積層板を製造する工程により製造された積層板を用いることを特徴とする多層プリント配線板の製造方法。
[式(1)中、複数のR1は、それぞれ独立にアルキル基、フェニル基又は置換フェニル基を示し、互いに同じでも異なっていても良く、複数のR2は、それぞれ独立にアルキル基、フェニル基又は置換フェニル基を示し、互いに同じでも異なっていても良く、R3及びR4はそれぞれ独立にアルキル基、フェニル基又は置換フェニル基を示し、R5及びR6はそれぞれ独立に2価の有機基を示し、nは2〜50の整数を示す。]
[式(2)中、R9は複数ある場合は各々独立に、酸性置換基である水酸基、カルボキシル基又はスルホン酸基を示し、R10は複数ある場合は各々独立に水素原子、炭素数1〜5の脂肪族炭化水素基、ハロゲン原子を示し、xは1〜5の整数、yは0〜4の整数で、x+y=5である。]
0.1≦〔C=C基当量〕/〔−NH2基当量の総和〕≦10.0に示す範囲になることが好ましい。より好ましくは、この関係が、
1.0≦〔C=C基当量〕/〔−NH2基当量の総和〕≦9.0、特に好ましくは、
2.0≦〔C=C基当量〕/〔−NH2基当量の総和〕≦8.0
の範囲とする。
該当量比を0.1以上とすることによりゲル化及び耐熱性が低下することがなく、又、10.0以下とすることにより有機溶剤への溶解性、耐熱性が低下することがない。
また、(C)成分の使用量は、(A)成分100質量部に対して1〜1000質量部が好ましく、10〜500質量部がより好ましい。1質量部以上とすることにより耐熱性が低下することがなく、又、1000質量部以下とすることにより低熱膨張性を良好に保つことができる。
0.1≦〔C=C基当量〕/〔−NH2基当量の総和〕≦10.0に示す範囲になることが好ましい。より好ましくは、この関係が、
1.0≦〔C=C基当量〕/〔−NH2基当量の総和〕≦9.0、特に好ましくは、
2.0≦〔C=C基当量〕/〔−NH2基当量の総和〕≦8.0
の範囲とする。
該当量比を0.1以上とすることによりゲル化及び耐熱性が低下することがなく、又、10.0以下とすることにより有機溶剤への溶解性、耐熱性が低下することがないので、好ましい。
(D)成分の使用量は、上記関係を維持しつつ、(A)成分100質量部に対して50〜3000質量部が好ましく、100〜1500質量部がより好ましい。50質量部以上とすることにより耐熱性が低下することがなく、又、3000質量部以下とすることによって、低熱膨張性を良好に保つことができる。
有機溶剤の使用量は、(A)、(B)、(C)、(D)の総和100質量部当たり、25〜1000質量部とすることが好ましく、50〜500質量部とすることがより好ましい。有機溶剤の使用量が25〜1000質量部とすると、溶解性の不足や、合成に長時間を要するなどのデメリットがなくて好ましい。
併用する熱硬化性樹脂は、特に制限されないが、例えば、エポキシ樹脂、フェノール樹脂、不飽和イミド樹脂、シアネート樹脂、イソシアネート樹脂、ベンゾオキサジン樹脂、オキセタン樹脂、アミノ樹脂、不飽和ポリエステル樹脂、アリル樹脂、ジシクロペンタジエン樹脂、シリコーン樹脂、トリアジン樹脂、メラミン樹脂等が挙げられ、これらは単独で、あるいは2種類以上を混合して使用してもよい。これらの中で、成形性や電気絶縁性の点からエポキシ樹脂、シアネート樹脂が好ましい。
本発明のプリプレグは、本発明の熱硬化性樹脂組成物を、基材に含浸又は塗工し、加熱等により半硬化(Bステージ化)して本発明のプリプレグを製造することができる。本発明の基材として、各種の電気絶縁材料用積層板に用いられている周知のものが使用できる。その材質の例としては、Eガラス、Dガラス、Sガラス及びQガラス等の無機物繊維、ポリイミド、ポリエステル及びテトラフルオロエチレン等の有機繊維、並びにそれらの混合物等が挙げられる。
積層板を製造する際の成形条件は、例えば、電気絶縁材料用積層板及び多層板の手法が適用でき、例えば多段プレス、多段真空プレス、連続成形、オートクレーブ成形機等を使用し、温度100〜250℃、圧力0.2〜10MPa、加熱時間0.1〜5時間の範囲で成形することができる。また、本発明のプリプレグと内層用配線板とを組合せ、積層成形して、積層板を製造することもできる。
なお、各実施例および比較例得られた銅張積層板を用いて、ガラス転移温度、熱膨張率、銅箔接着性、吸湿性、吸湿はんだ耐熱性、銅付きはんだ耐熱性について以下の方法で測定・評価した。
銅張積層板を銅エッチング液に浸漬することにより銅箔を取り除いた5mm角の評価基板を作製し、TMA試験装置(デュポン社製、TMA2940)を用いて圧縮法で熱機械分析を行った。評価基板を前記装置にZ方向に装着後、荷重5g、昇温速度10℃/分の測定条件にて連続して2回測定した。2回目の測定における熱膨張曲線の異なる接線の交点で示されるTgを求め、耐熱性を評価した。
銅張積層板を銅エッチング液に浸漬することにより銅箔を取り除いた5mm角の評価基板を作製し、TMA試験装置(デュポン社製、TMA2940)を用いて圧縮法で熱機械分析をおこなった。評価基板を前記装置にX方向に装着後、荷重5g、昇温速度10℃/分の測定条件にて連続して2回測定した。2回目の測定における30℃から100℃の平均熱膨張率を算出し、これを熱膨張率の値とした。
銅張積層板を銅エッチング液に浸漬することにより3mm幅の銅箔を形成して評価基板を作製し、引張り試験機を用いて銅箔の接着性(ピール強度)を測定した。
銅張積層板を銅エッチング液に浸漬することにより銅箔を取り除いた評価基板を作製し、平山製作所(株)製プレッシャー・クッカー試験装置を用いて、121℃、2atmの条件で5時間までプレッシャー・クッカー処理を行った後、評価基板の吸水率を測定した。
銅張積層板を銅エッチング液に浸漬することにより銅箔を取り除いた5cm角の評価基板を作製し、平山製作所(株)製プレッシャー・クッカー試験装置を用いて、121℃、0.2MPaの条件で4時間までプレッシャー・クッカー処理を行った後、温度288℃のはんだ浴に、評価基板を20秒間浸漬した後、外観を観察することによりはんだ耐熱性を評価した。
銅張積層板から25mm角の評価基板を作製し、温度288℃のはんだ浴に、120分間評価基板をフロートし、外観を観察することにより銅付きはんだ耐熱性を評価した。
温度計、攪拌装置、還流冷却管付き水分定量器の付いた加熱及び冷却可能な容積2リットルの反応容器に、KF−8010:75.7gと、ビス(4−マレイミドフェニル)メタン:168.0gと、p−アミノフェノール:6.4g、及びジメチルアセトアミド:250.0gを入れ、100℃で3時間反応させて、変性シリコーン化合物(1−1)含有溶液を得た。
温度計、攪拌装置、還流冷却管付き水分定量器の付いた加熱及び冷却可能な容積2リットルの反応容器に、X−22−161A:99.2gと、3、3’−ジエチル−4、4’−ジアミノジフェニルメタン:164.3gと、m−アミノフェノール:4.5g、及びジメチルアセトアミド:250.0gを入れ、100℃で3時間反応させて、変性シリコーン化合物(1−2)含有溶液を得た。
温度計、攪拌装置、還流冷却管付き水分定量器の付いた加熱及び冷却可能な容積2リットルの反応容器に、X−22−1660B−3:172.0gと、ポリフェニルメタンマレイミド:75.1gと、p−アミノフェノール:2.8g、及びプロピレングリコールモノメチルエーテル:250.0gを入れ、115℃で3時間反応させて、変性シリコーン化合物(1−3)含有溶液を得た。
温度計、攪拌装置、還流冷却管付き水分定量器の付いた加熱及び冷却可能な容積2リットルの反応容器に、KF−8012:172.0gと、ビス(4−マレイミドフェニル)メタン:75.1gと、p−アミノフェノール:2.8g、及びプロピレングリコールモノメチルエーテル:250.0gを入れ、115℃で3時間反応させて、変性シリコーン化合物(1−4)含有溶液を得た。
温度計、攪拌装置、還流冷却管付き水分定量器の付いた加熱及び冷却可能な容積2リットルの反応容器に、KF−8012:88.0gと、3、3’−ジエチル−4、4’−ジアミノジフェニルメタン:14.0gと、ビス(4−マレイミドフェニル)メタン:143.0gと、p−アミノフェノール:5.5g、及びプロピレングリコールモノメチルエーテル:250.0gを入れ、115℃で3時間反応させて、変性シリコーン化合物(1−5)含有溶液を得た。
温度計、攪拌装置、還流冷却管付き水分定量器の付いた加熱及び冷却可能な容積2リットルの反応容器に、KF−8012:88.0gと、3、3’−ジアミノジフェニルスルホン:14.0gと、ビス(4−マレイミドフェニル)メタン:143.0gと、p−アミノフェノール:5.5g、及びプロピレングリコールモノメチルエーテル:250.0gを入れ、115℃で3時間反応させて、変性シリコーン化合物(1−6)含有溶液を得た。
温度計、攪拌装置、還流冷却管の付いた加熱及び冷却可能な容積2リットルの反応容器に、ジアミノジフェニルメタン:16.1gと、ビス(4−マレイミドフェニル)メタン:236.0gと、p−アミノフェノール:18.0g、及びジメチルアセトアミド:230.0gを入れ、100℃で2時間反応させ、酸性置換基を有するポリイミド(1−7)含有溶液を得た。
温度計、攪拌装置、還流冷却管の付いた加熱及び冷却可能な容積2リットルの反応容器に、2、2’−ビス[4−(4−アミノフェノキシ)フェニル]プロパン:31.7gと、ビス(4−マレイミドフェニル)メタン:236.0gと、p−アミノフェノール:17.2g、及びプロピレングリコールモノメチルエーテル:230.0gを入れ、120℃で4時間反応させ、酸性置換基を有するポリイミド(1−8)含有溶液を得た。
製造実施例1〜6で得られた変性シリコーン化合物含有溶液又は製造比較例1〜2で得られたポリイミド含有溶液と、以下に示す熱硬化性樹脂、無機充填剤、硬化促進剤、及び希釈溶剤にメチルエチルケトンを使用して、第1表〜第3表に示した配合割合(質量部)で混合して樹脂分65質量%の均一なワニスを得た。
次に、上記ワニスを厚さ0.1mmのEガラスクロスに含浸塗工し、160℃で10分加熱乾燥して樹脂含有量48質量%のプリプレグを得た。
このプリプレグを4枚重ね、12μmの電解銅箔を上下に配置し、圧力2.5MPa、温度240℃で60分間プレスを行って、銅張積層板を得た。
得られた銅張積層板の測定・評価結果を第1表〜第3表に示す。
PT−30:ノボラック型シアネート樹脂〔ロンザジャパン(株)製、商品名〕、
BA230:ビスフェノールAジシアネートプレポリマー〔ロンザジャパン(株)製、商品名:〕、
EXA−47104:官能ナフタレン型エポキシ樹脂〔大日本インキ化学工業(株)製、商品名〕、
NC−3000−H、ビフェニルアラルキル型エポキシ樹脂〔日本化薬(株)製、商品名:〕、
EXB−9500:ナフタレン型フェノール樹脂〔大日本インキ化学工業(株)製、商品名:〕
(無機充填剤)
SC2050−KNK:溶融シリカ〔アドマテック(株)製、商品名:〕、
BMT−3LVベーマイト〔河合石灰工業(株)製、商品名:〕、
(硬化促進剤):
G−8009L:イソシアネートマスクイミダゾール〔第一工業製薬(株)製、商品名:〕、
Claims (10)
- 少なくとも(A)下記一般式(1)に示すシロキサンジアミン由来の構造単位及び(B)分子中に少なくとも2個のN−置換マレイミド基を有するマレイミド化合物由来の構造単位を有する変性シリコーン化合物を含有するマレイミド樹脂組成物。
[式(1)中、複数のR1は、それぞれ独立にアルキル基、フェニル基又は置換フェニル基を示し、互いに同じでも異なっていても良く、複数のR2は、それぞれ独立にアルキル基、フェニル基又は置換フェニル基を示し、互いに同じでも異なっていても良く、R3及びR4はそれぞれ独立にアルキル基、フェニル基又は置換フェニル基を示し、R5及びR6はそれぞれ独立に2価の有機基を示し、nは2〜50の整数を示す。] - さらに、無機充填剤を含有する請求項1に記載のマレイミド樹脂組成物。
- 前記変性シリコーン化合物が、さらに(C)下記一般式(2)に示す酸性置換基を有するアミン化合物由来の構造単位を含み、且つ、前記(A)一般式(1)に示すシロキサンジアミン由来の構造単位と前記(C)一般式(2)に示す酸性置換基を有するアミン化合物由来の構造単位の含有量が、それぞれ前記一般式(1)に示すシロキサンジアミンと前記一般式(2)に示す酸性置換基を有するアミン化合物の使用量換算で、−NH2基当量の総和と、(B)成分のC=C基当量との関係が、
2.0≦〔C=C基当量〕/〔−NH2基当量の総和〕≦8.0
に示す範囲になる請求項1又は2に記載のマレイミド樹脂組成物。
[式(2)中、R9は複数ある場合は各々独立に、酸性置換基である水酸基、カルボキシル基又はスルホン酸基を示し、R10は複数ある場合は各々独立に水素原子、炭素数1〜5の脂肪族炭化水素基、ハロゲン原子を示し、xは1〜5の整数、yは0〜4の整数で、x+y=5である。] - 変性シリコーン化合物の含有量が樹脂成分の総和100質量部当たり20〜100質量部である請求項1〜3のいずれか一項に記載のマレイミド樹脂組成物。
- 熱硬化性樹脂として、さらに、エポキシ樹脂及び/又はシアネート樹脂を含有する請求項1〜4のいずれか一項に記載のマレイミド樹脂組成物。
- 請求項1〜5のいずれか一項に記載のマレイミド樹脂組成物の硬化物。
- 請求項1〜5のいずれか一項に記載のマレイミド樹脂組成物、又は請求項6に記載の硬化物を含有するプリプレグ。
- 温度100〜250℃、圧力0.2〜10MPa、加熱時間0.1〜5時間の条件で成形可能な請求項7に記載のプリプレグ。
- 請求項7又は8に記載のプリプレグを用いてなる積層板。
- 請求項9に記載の積層板を用いてなる多層プリント配線板。
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US11401381B2 (en) | 2022-08-02 |
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WO2012099133A1 (ja) | 2012-07-26 |
US20130330563A1 (en) | 2013-12-12 |
EP2666804A1 (en) | 2013-11-27 |
TW201245284A (en) | 2012-11-16 |
JP2016074907A (ja) | 2016-05-12 |
KR20180135079A (ko) | 2018-12-19 |
TWI573817B (zh) | 2017-03-11 |
TW201710322A (zh) | 2017-03-16 |
TWI586713B (zh) | 2017-06-11 |
KR101927723B1 (ko) | 2019-03-12 |
JP2017057409A (ja) | 2017-03-23 |
JP5835233B2 (ja) | 2015-12-24 |
CN103328543A (zh) | 2013-09-25 |
JPWO2012099133A1 (ja) | 2014-06-30 |
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