JP5713045B2 - エポキシ樹脂組成物、その硬化物、及びプリント配線基板 - Google Patents
エポキシ樹脂組成物、その硬化物、及びプリント配線基板 Download PDFInfo
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- JP5713045B2 JP5713045B2 JP2013084825A JP2013084825A JP5713045B2 JP 5713045 B2 JP5713045 B2 JP 5713045B2 JP 2013084825 A JP2013084825 A JP 2013084825A JP 2013084825 A JP2013084825 A JP 2013084825A JP 5713045 B2 JP5713045 B2 JP 5713045B2
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- 238000003786 synthesis reaction Methods 0.000 description 7
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- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 4
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- 238000004132 cross linking Methods 0.000 description 4
- 150000007973 cyanuric acids Chemical class 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000005350 fused silica glass Substances 0.000 description 4
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- 239000012796 inorganic flame retardant Substances 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920001568 phenolic resin Polymers 0.000 description 4
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 3
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- 239000004593 Epoxy Substances 0.000 description 3
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
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- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- FOZHTJJTSSSURD-UHFFFAOYSA-J titanium(4+);dicarbonate Chemical compound [Ti+4].[O-]C([O-])=O.[O-]C([O-])=O FOZHTJJTSSSURD-UHFFFAOYSA-J 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-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
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 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
- PZRXQXJGIQEYOG-UHFFFAOYSA-N zinc;oxido(oxo)borane Chemical compound [Zn+2].[O-]B=O.[O-]B=O PZRXQXJGIQEYOG-UHFFFAOYSA-N 0.000 description 1
Description
で表される芳香族リン化合物(α)とホルムアルデヒド(β)とを反応させて得られ、リン原子1個に対するメチレン炭素原子の含有率が1.4〜5個の範囲にあるものであり、かつ、エポキシ樹脂組成物中のリン原子含有量が0.5〜4質量%の範囲であることを特徴とするエポキシ樹脂組成物に関する。
本発明で用いるエポキシ樹脂(A)は、種々のエポキシ樹脂を用いることができるが、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型エポキシ樹脂等のビスフェノール型エポキシ樹脂;ビフェニル型エポキシ樹脂、テトラメチルビフェニル型エポキシ樹脂等のビフェニル型エポキシ樹脂;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、フェノール類とフェノール性水酸基を有する芳香族アルデヒドとの縮合物のエポキシ化物、ビフェニルノボラック型エポキシ樹脂等のノボラック型エポキシ樹脂;トリフェニルメタン型エポキシ樹脂;テトラフェニルエタン型エポキシ樹脂;ジシクロペンタジエン−フェノール付加反応型エポキシ樹脂;フェノールアラルキル型エポキシ樹脂;ナフトールノボラック型エポキシ樹脂、ナフトールアラルキル型エポキシ樹脂、ナフトール−フェノール共縮ノボラック型エポキシ樹脂、ナフトール−クレゾール共縮ノボラック型エポキシ樹脂、ジグリシジルオキシナフタレン、1,1−ビス(2,7−ジグリシジルオキシ−1−ナフチル)アルカン等の分子構造中にナフタレン骨格を有するエポキシ樹脂;リン原子含有エポキシ樹脂等が挙げられる。また、これらのエポキシ樹脂は単独で用いてもよく、2種以上を混合してもよい。
(式中、R1、R2はそれぞれ独立的に、水素原子、炭素原子数1〜4のアルキル基、フェニル基、アラルキル基を表す。)で表される芳香族燐化合物とホルムアルデヒドとを反応させて得られるメチロール基を含有する芳香族リン化合物である。本発明では上記メチロール基含有芳香族リン化合物(C)のなかでも特に該化合物中のメチレン炭素原子の含有率が、リン原子1個に対して1.4〜5の範囲にあるものが、メチロール基の数が十分に高くなり、硬化物の架橋密度が向上して耐熱性が向上すると共に、更に硬化物中に効率良くリン含有骨格が取り込まれる結果、燃焼時に優れた難燃効果を示し、単にHCAを配合した場合に比べ、低リン濃度でも十分な難燃性を得られる点から好ましい。
(式中、R1、R2、R3及びR4はそれぞれ独立的に、水素原子、炭素原子数1〜4のアルキル基、フェニル基、アラルキル基を表し、X1、X2、X3、X4、X5、X6、X7及びX8はそれぞれ独立的に水素原子、又は下記構造式(Y)
(式中、R1、R2はそれぞれ独立的に、水素原子、炭素原子数1〜4のアルキル基、フェニル基、アラルキル基を表す。)で表される芳香族リン化合物(α)とホルムアルデヒド(β)とを反応させて製造することができる。
攪拌装置を備えた4つ口フラスコに9,10−ジヒドロ−9−オキサ−10−フォスファフェナントレン−10−オキサイド216gと41.5%ホルマリン144.6gと蓚酸2.16gとを仕込み、100℃に昇温し、100℃で3時間保った後、単蒸留しながら140℃まで昇温し、140℃で蒸留を続けながら41.5%ホルマリン72.3gを1時間かけて少しづつ滴下し、140℃で2時間保った後、単蒸留しながら180℃まで昇温し、180℃で蒸留を続けながら41.5質量%ホルマリン72.3gを1時間かけて少しづつ滴下し、180℃で2時間保ち、さらに200℃まで昇温し1時間保った。その後、減圧下、未反応のホルムアルデヒドと水分を除去することにより、リン変性硬化剤(A−1)248gを得た。得られたリン変性硬化剤(A−1)中のメチレン炭素原子含有率はリン原子1モルに対して1.4モルとなる割合、リン含有率は12.5質量%であった。
攪拌装置を備えた4つ口フラスコに9,10−ジヒドロ−9−オキサ−10−フォスファフェナントレン−10−オキサイド216gと41.5%ホルマリン216.9gと蓚酸2.16gとを仕込み、100℃に昇温し、100℃で3時間保った後、単蒸留しながら140℃まで昇温し、140℃で蒸留を続けながら41.5質量%ホルマリン72.3gを1時間かけて少しづつ滴下し、140℃で2時間保った後、単蒸留しながら180℃まで昇温し、180℃で蒸留を続けながら41.5%ホルマリン72.3gを1時間かけて少しづつ滴下し、180℃で2時間保ち、さらに200℃まで昇温し1時間保った。その後、減圧下、未反応のホルムアルデヒドと水分を除去することにより、リン変性硬化剤(A−2)251gを得た。得られたリン変性硬化剤(A−2)のメチレン炭素原子含有率はリン原子1モルに対して2.0モルとなる割合、リン含有率は12.3質量%であった。
攪拌装置を備えた4つ口フラスコに9,10−ジヒドロ−9−オキサ−10−フォスファフェナントレン−10−オキサイド216gと41.5質量%ホルマリン144.6gと蓚酸1.08gとを仕込み、100℃に昇温し、100℃で3時間保った後、単蒸留しながら140℃まで昇温し、140℃で蒸留を続けながら41.5%ホルマリン72.3gを30分かけて少しづつ滴下し、140℃で2時間保った後、単蒸留しながら180℃まで昇温し、180℃で蒸留を続けながら41.5%ホルマリン72.3gを1時間かけて少しづつ滴下し、180℃で2時間保って、リン変性硬化剤(A−3)243gを得た。得られたリン変性硬化剤(A−3)のメチレン炭素原子含有率はリン原子1モルに対して0.9モルとなる割合、リン含有率は12.8質量%であった。また、未反応9,10−ジヒドロ−9−オキサ−10−フォスファフェナントレン−10−オキサイドは2.6%であった。
下記表1記載の配合に従い、エポキシ樹脂として、DIC(株)製N−690(クレゾールノボラック型エポキシ樹脂、エポキシ当量:215g/eq)、エポキシ樹脂硬化剤としてDIC(株)製TD−2090(フェノールノボラック樹脂、水酸基当量:105g/eq)及びジシアンジアミド(DICY)、リン変性硬化剤として(A−1)、(A−2)、硬化促進剤として2−エチル−4−メチルイミダゾール(2E4MZ)を配合し、最終的に各組成物の不揮発分(N.V.)が58質量%となるようにメトキシプロパノールを配合して調整した。
次いで、下記の如き条件で硬化させて積層板を試作し、下記の方法で耐熱性及び難燃性を評価した。結果を表1に示す。
基材:日東紡績株式会社製 ガラスクロス「#2116」(210×280mm)
プライ数:6 プリプレグ化条件:160℃
硬化条件:200℃、40kg/cm2で1.5時間、成型後板厚:0.8mm
熱機械分析装置(TMA:セイコーインスツルメント社製SS−6100)を用いて、圧縮モードで熱機械分析を行った。(測定架重:88.8mN、昇温速度:3℃/分で2回、測定温度範囲:−50℃から300℃)2回目の測定における、線膨張率の変位点の値をガラス転移温度として評価した。
UL−94試験法に準拠し、厚さ0.8mmの試験片5本用いて燃焼試験を行った。
A−1:合成例1で得られたリン変性硬化剤(A−1)
A−2:合成例2で得られたリン変性硬化剤(A−2)
A−3:合成例3で得られたリン変性硬化剤(A−3)
DICY:ジシアンジアミド
TD−2090:フェノールノボラック型フェノール樹脂(DIC(株)製「TD−2090」、水酸基当量105g/eq)
N−690:DIC(株)製クレゾールノボラック型エポキシ樹脂(「エピクロンN−690」、エポキシ当量:215g/eq)
2E4MZ:2−エチル−4−メチルイミダゾール
表1の脚注:
*1:1回の接炎における最大燃焼時間(秒)
*2:試験片5本の合計燃焼時間(秒)
Claims (5)
- エポキシ樹脂(A)、メチロールに対して求核反応性を有するエポキシ樹脂用硬化剤(B)、及びメチロール基含有芳香族リン化合物(C)を必須成分とするエポキシ樹脂組成物であって、前記メチロール基含有芳香族リン化合物(C)が下記構造式(1)
で表される芳香族リン化合物(α)とホルムアルデヒド(β)とを反応させて得られ、リン原子1個に対するメチレン炭素原子の含有率が1.4〜5個の範囲にあるものであり、かつ、エポキシ樹脂組成物中のリン原子含有量が0.5〜4質量%の範囲であることを特徴とするエポキシ樹脂組成物。 - 前記メチロール基含有芳香族リン化合物(C)が、下記構造式(C1)
で表される化合物(c1)又は下記構造式(C2)
で表される化合物(c2)の何れかである請求項1記載のエポキシ樹脂組成物。 - 前記エポキシ樹脂用硬化剤(B)がジシアンジアミド又はフェノール系硬化剤である請求項1又は2記載のエポキシ樹脂組成物。
- 請求項1〜3の何れか1つに記載のエポキシ樹脂組成物を硬化反応させてなることを特徴とする硬化物。
- 請求項1〜3の何れか1つに記載のエポキシ樹脂組成物に、更に有機溶剤(D)を配合してワニス化した樹脂組成物を、補強基材に含浸し銅箔を重ねて加熱圧着させることにより得られたプリント配線基板。
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