JP2008195907A - Thermosetting benzoxazine resin composition - Google Patents
Thermosetting benzoxazine resin composition Download PDFInfo
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- JP2008195907A JP2008195907A JP2007035590A JP2007035590A JP2008195907A JP 2008195907 A JP2008195907 A JP 2008195907A JP 2007035590 A JP2007035590 A JP 2007035590A JP 2007035590 A JP2007035590 A JP 2007035590A JP 2008195907 A JP2008195907 A JP 2008195907A
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- benzoxazine
- benzoxazine compound
- resin composition
- thermosetting
- benzoxazine resin
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- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 14
- 239000011342 resin composition Substances 0.000 title claims abstract description 12
- -1 benzoxazine compound Chemical class 0.000 claims abstract description 36
- 239000000126 substance Substances 0.000 claims description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 150000005130 benzoxazines Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000004917 carbon fiber Substances 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 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 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- MQCPOLNSJCWPGT-UHFFFAOYSA-N 2,2'-Bisphenol F Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1O MQCPOLNSJCWPGT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000002648 laminated material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Description
本発明は、熱硬化性ベンゾオキサジン樹脂組成物に関する。 The present invention relates to a thermosetting benzoxazine resin composition.
ベンゾオキサジン化合物に関する研究は古くから行われており（例えば、特許文献１）、フェノール類、アミン類、ホルムアルデヒドを反応させることにより合成される（化１の反応式参照）。 Studies on benzoxazine compounds have been conducted for a long time (for example, Patent Document 1), and they are synthesized by reacting phenols, amines and formaldehyde (see the reaction formula of Chemical Formula 1).
このベンゾオキサジン化合物（モノマー）は、加熱することにより開環重合して硬化物であるベンゾオキサジン樹脂（ポリマー）を生成するので、従来の熱硬化性樹脂として知られるエポキシ樹脂やフェノール樹脂に代わる新しいタイプの樹脂として注目されている。
このベンゾオキサジン樹脂は優れた耐熱性、難燃性、耐水性、低熱膨張性（寸法安定性）および電気的特性等を有し、またベンゾオキサジン樹脂の成形物はベンゾオキサジン化合物の溶融体から容易に製造することができ、その成形時には、反応副生物を放出することなくベンゾオキサジン化合物が硬化するので、フェノール樹脂等に比べて歩留まりの向上や成形時に発泡を抑止できるなどの有利な特徴も備えている。また、エポキシ樹脂とは異なって、基本的には硬化剤を必要としない。
This benzoxazine compound (monomer) is ring-opening polymerized by heating to produce a cured benzoxazine resin (polymer), which is a new alternative to epoxy resins and phenol resins known as conventional thermosetting resins. It is attracting attention as a type of resin.
This benzoxazine resin has excellent heat resistance, flame retardancy, water resistance, low thermal expansion (dimensional stability), electrical properties, etc., and the molded product of benzoxazine resin is easy from the melt of benzoxazine compound Since the benzoxazine compound is cured without releasing reaction by-products during molding, it has advantageous features such as improved yield and suppression of foaming during molding. ing. Unlike epoxy resins, basically no curing agent is required.
近年、分子中にベンゾオキサジン環を２つ有する２官能性のベンゾキサジン化合物が注目され、とりわけ、硬化物とした場合の電気的特性が優れ、且つ比較的安価に製造可能であるところから、化２の化学式（Ａ）で示されるベンゾオキサジン化合物（以下、ベンゾオキサジン化合物（Ａ）と云う）の利用が広く検討されている。 In recent years, bifunctional benzoxazine compounds having two benzoxazine rings in the molecule have attracted attention, and in particular, since they have excellent electrical properties when cured and can be produced at a relatively low cost, The use of a benzoxazine compound represented by the chemical formula (A) (hereinafter referred to as benzoxazine compound (A)) has been widely studied.
しかしながら、このベンゾオキサジン化合物（Ａ）も、従来知られた他のベンゾオキサジン化合物と同様に熱硬化させた場合には、その硬化物が硬くて脆い、即ち靱性が乏しい、と云う難点を有している。 However, this benzoxazine compound (A) also has the disadvantage that when it is heat-cured like other conventionally known benzoxazine compounds, the cured product is hard and brittle, that is, the toughness is poor. ing.
本発明は、優れた靱性を有する硬化物が得られる熱硬化性ベンゾオキサジン樹脂組成物を提供することを目的とする。 An object of this invention is to provide the thermosetting benzoxazine resin composition from which the hardened | cured material which was excellent in toughness is obtained.
本発明者は、上記の課題を解決するために鋭意研究を重ねた結果、前記のベンゾオキサジン化合物（Ａ）を熱硬化させる際に、化３の化学式（Ｂ）で示されるベンゾオキサジン化合物（以下、ベンゾオキサジン化合物（Ｂ）と云う）を併用すると、硬化物の靱性が向上することを見出して、本発明を完遂するに至ったものである。
即ち、本発明は、ベンゾオキサジン化合物（Ａ）とベンゾオキサジン化合物（Ｂ）を含有することを特徴とする熱硬化性ベンゾオキサジン樹脂組成物である。
As a result of intensive studies in order to solve the above-mentioned problems, the present inventor has obtained a benzoxazine compound represented by the chemical formula (B) of the chemical formula (B) (hereinafter referred to as the benzoxazine compound (A)) when the benzoxazine compound (A) is thermally cured. The benzoxazine compound (B)) was used in combination to find that the toughness of the cured product was improved, and the present invention was accomplished.
That is, this invention is a thermosetting benzoxazine resin composition characterized by containing a benzoxazine compound (A) and a benzoxazine compound (B).
本発明の熱硬化性ベンゾオキサジン樹脂組成物の有効成分であるベンゾオキサジン化合物（Ａ）および同（Ｂ）は、化学構造は異なるものの、共にベンゾオキサジン環を有する点で共通しているので、耐水性や難燃性などベンゾオキサジン樹脂が本来有する特性を損なうことなく、靱性を高めることができる。 The benzoxazine compounds (A) and (B), which are the active ingredients of the thermosetting benzoxazine resin composition of the present invention, are common in that they have a benzoxazine ring, although they have different chemical structures. The toughness can be increased without impairing the inherent properties of the benzoxazine resin, such as properties and flame retardancy.
以下、本発明を詳細に説明する。
本発明の実施において使用されるベンゾオキサジン化合物（Ａ）は、公知の方法に従って、Ｐ−クレゾール、ヘキサメチレンジアミンおよびホルムアルデヒドから合成することができる。また同様に、ベンゾオキサジン化合物（Ｂ）は、メチレンビスフェノール（ビスフェノールＦ）、アニリンおよびホルムアルデヒドから合成することができる。
Hereinafter, the present invention will be described in detail.
The benzoxazine compound (A) used in the practice of the present invention can be synthesized from P-cresol, hexamethylenediamine and formaldehyde according to a known method. Similarly, the benzoxazine compound (B) can be synthesized from methylene bisphenol (bisphenol F), aniline and formaldehyde.
本発明の熱硬化性ベンゾオキサジン樹脂組成物は、前記ベンゾオキサジン化合物（Ａ）およびベンゾオキサジン化合物（Ｂ）を一般的な方法で混合した後、熱ロール法またはニーダー法などの公知の方法によって、混練して製造することができる。次いで該組成物を溶融させ、圧縮成形、トランスファー成形あるいは注型などの方法により、１７０℃以上の加熱温度で硬化成形を行なうことができる。
本発明の実施においては、ベンゾオキサジン化合物（Ｂ）の使用量を、ベンゾオキサジン化合物（Ａ）１００重量部に対して、１０〜５０重量部とすることが好ましい。ベンゾオキサジン化合物（Ｂ）の使用量が１０重量部より少ないと、満足すべき靱性向上の効果が得られず、また５０重量部より多くしても靱性は高まることなくほぼ一定である。
The thermosetting benzoxazine resin composition of the present invention is prepared by mixing the benzoxazine compound (A) and the benzoxazine compound (B) by a general method, and then by a known method such as a heat roll method or a kneader method. It can be produced by kneading. Next, the composition can be melted and cured and molded at a heating temperature of 170 ° C. or higher by a method such as compression molding, transfer molding or casting.
In the practice of the present invention, the amount of the benzoxazine compound (B) used is preferably 10 to 50 parts by weight with respect to 100 parts by weight of the benzoxazine compound (A). When the amount of the benzoxazine compound (B) used is less than 10 parts by weight, a satisfactory toughness improving effect cannot be obtained.
本発明の熱硬化性ベンゾオキサジン樹脂組成物には、必要に応じて、シリカ、アルミナ、水酸化アルミニウム、ガラス、タルク、クレー、マイカ、炭酸カルシウム、カーボン等の充填材、ガラス繊維、カーボン繊維などの繊維状強化材や色素、離型剤など、従来公知の各種充填剤、添加剤を組み合わせて配合することができる。 If necessary, the thermosetting benzoxazine resin composition of the present invention includes silica, alumina, aluminum hydroxide, glass, talc, clay, mica, calcium carbonate, carbon and other fillers, glass fibers, carbon fibers, etc. Various known fillers and additives such as a fibrous reinforcing material, a pigment, and a release agent can be blended in combination.
また、本発明の熱硬化性ベンゾオキサジン樹脂組成物を、トルエン、キシレン、アセトン、メチルエチルケトン、メチルイソブチルケトン等の溶剤に溶解させてワニスを調製し、該ワニスを銅箔、ポリイミドフィルム、ポリエチレンテレフタレートフィルム等の上に塗布し、加熱することによりフィルム状の硬化物を得ることができる。
あるいは、前記のワニスをガラス繊維、カ−ボン繊維、ポリエステル繊維、ポリアミド繊維、アルミナ繊維、紙等の基材に含浸させて乾燥したプリプレグを、加熱加圧して硬化物とすることも可能である。
Moreover, the thermosetting benzoxazine resin composition of the present invention is dissolved in a solvent such as toluene, xylene, acetone, methyl ethyl ketone, methyl isobutyl ketone to prepare a varnish, and the varnish is copper foil, polyimide film, polyethylene terephthalate film. A film-like cured product can be obtained by applying the composition on the substrate and heating.
Alternatively, a prepreg dried by impregnating a substrate such as glass fiber, carbon fiber, polyester fiber, polyamide fiber, alumina fiber or paper with the above varnish can be heated and pressurized to obtain a cured product. .
本発明の熱硬化性ベンゾオキサジン樹脂組成物は、電子部品の封止材料、注型材料、回路基板の成型材料、積層材料、塗料、接着剤、レジストインクなどとして好適なものである。 The thermosetting benzoxazine resin composition of the present invention is suitable as a sealing material for electronic parts, a casting material, a molding material for circuit boards, a laminated material, a paint, an adhesive, a resist ink, and the like.
なお、本発明においては、ベンゾオキサジン化合物（Ａ）の硬化物の靱性を高めるために、ベンゾオキサジン化合物（Ａ）の硬化時にベンゾオキサジン化合物（Ｂ）を併用する手段を採用したが、ベンゾオキサジン化合物（Ａ）以外の従来知られたベンゾオキサジン化合物の硬化物の靱性を高めるに当たっても、ベンゾオキサジン化合物（Ｂ）を併用する手段が有効であることが期待される。ベンゾオキサジン化合物（Ａ）以外の従来知られたベンゾオキサジン化合物としては、例えば、化４〜６の化学式（Ｃ）〜（Ｅ）で示されるベンゾオキサジン化合物や、３核体以上のフェノールノボラック、アニリンおよびホルムアルデヒドを原料として合成されるベンゾオキサジン化合物等が挙げられる。 In the present invention, in order to increase the toughness of the cured product of the benzoxazine compound (A), a means of using the benzoxazine compound (B) together with the benzoxazine compound (A) is adopted. It is expected that the means for using the benzoxazine compound (B) together is effective in increasing the toughness of a conventionally known cured product of the benzoxazine compound other than (A). Examples of conventionally known benzoxazine compounds other than the benzoxazine compound (A) include, for example, benzoxazine compounds represented by chemical formulas (C) to (E) of Chemical Formulas 4 to 6, phenol novolacs having three or more nuclei, and anilines. And benzoxazine compounds synthesized from formaldehyde as a raw material.
また、ベンゾオキサジン化合物の有効成分として、ベンゾオキサジン化合物（Ｂ）のみとした場合においても、優れた靱性を有する硬化物が得られることが期待される。 Further, even when only the benzoxazine compound (B) is used as the active ingredient of the benzoxazine compound, it is expected that a cured product having excellent toughness can be obtained.
以下、本発明を実施例および比較例によって具体的に説明するが、本発明はこれらに限定されるものではない。なお、実施例および比較例において使用した原料は次のとおりである。 EXAMPLES Hereinafter, although an Example and a comparative example demonstrate this invention concretely, this invention is not limited to these. In addition, the raw material used in the Example and the comparative example is as follows.
［原料］
・ベンゾオキサジン化合物（Ａ）：米国特許第２８２６５７６号公報に記載された方法に準拠して合成し、アメ状の液体を得た。
・ベンゾオキサジン化合物（Ｂ）：特開２００２−３３８６４８号公報に記載された方法に準拠して合成し、粉末状の固形物を得た。
[material]
Benzoxazine compound (A): synthesized according to the method described in US Pat. No. 2,826,576 to obtain a candy-like liquid.
Benzoxazine compound (B): synthesized in accordance with the method described in JP-A No. 2002-338648 to obtain a powdery solid.
〔実施例１〜３、比較例１〕
ベンゾオキサジン化合物（Ａ）およびベンゾオキサジン化合物（Ｂ）を、表１に示す配合割合で８０℃にて混合し、熱硬化性ベンゾオキサジン樹脂組成物を調製した。得られた組成物を１５０℃に加熱して、金型に注ぎ入れた後オーブンに入れ、１８０℃／４時間の加熱条件にて硬化させて、ダンベル型試験片を作成した。
前記の試験片について引張試験（JIS K 6911）を行い、破断伸び率（％）を測定したところ、得られた試験結果は表１に示したとおりであり、ベンゾオキサジン化合物（Ｂ）の含有割合が多くなるに従って、靱性が高められた。
[Examples 1 to 3, Comparative Example 1]
The benzoxazine compound (A) and the benzoxazine compound (B) were mixed at a blending ratio shown in Table 1 at 80 ° C. to prepare a thermosetting benzoxazine resin composition. The obtained composition was heated to 150 ° C., poured into a mold, placed in an oven, and cured under a heating condition of 180 ° C./4 hours to prepare a dumbbell-shaped test piece.
A tensile test (JIS K 6911) was performed on the above-mentioned test piece, and the elongation at break (%) was measured. The toughness increased with increasing.
Claims (1)
A thermosetting benzoxazine resin composition comprising a benzoxazine compound represented by Chemical Formula (A) of Chemical Formula 1 and a benzoxazine compound represented by Chemical Formula (B) of Chemical Formula 2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007035590A JP2008195907A (en) | 2007-02-16 | 2007-02-16 | Thermosetting benzoxazine resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007035590A JP2008195907A (en) | 2007-02-16 | 2007-02-16 | Thermosetting benzoxazine resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2008195907A true JP2008195907A (en) | 2008-08-28 |
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| JP2007035590A Pending JP2008195907A (en) | 2007-02-16 | 2007-02-16 | Thermosetting benzoxazine resin composition |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010018198A1 (en) * | 2008-08-14 | 2010-02-18 | Henkel Ag & Co. Kgaa | Polymerizable benzoxazine compositions |
| JP2010053324A (en) * | 2008-08-29 | 2010-03-11 | Sekisui Chem Co Ltd | Resin composition comprising benzoxadine ring-containing thermosetting resin |
| WO2020054218A1 (en) * | 2018-09-14 | 2020-03-19 | 積水化学工業株式会社 | Benzoxazine compound, curable resin composition, adhesive, adhesive film, cured object, circuit board, interlayer dielectric material, and multilayered printed wiring board |
| US11124608B2 (en) * | 2018-04-04 | 2021-09-21 | Case Western Reserve University | Polybenzoxazine resins with high hydrogen content, and composites therefrom |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11217416A (en) * | 1998-02-02 | 1999-08-10 | Showa Highpolymer Co Ltd | Thermosetting composition |
| JP2007009172A (en) * | 2005-05-31 | 2007-01-18 | Sekisui Chem Co Ltd | High dielectric composite molding |
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- 2007-02-16 JP JP2007035590A patent/JP2008195907A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11217416A (en) * | 1998-02-02 | 1999-08-10 | Showa Highpolymer Co Ltd | Thermosetting composition |
| JP2007009172A (en) * | 2005-05-31 | 2007-01-18 | Sekisui Chem Co Ltd | High dielectric composite molding |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010018198A1 (en) * | 2008-08-14 | 2010-02-18 | Henkel Ag & Co. Kgaa | Polymerizable benzoxazine compositions |
| JP2011530570A (en) * | 2008-08-14 | 2011-12-22 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェン | Polymerizable composition |
| JP2010053324A (en) * | 2008-08-29 | 2010-03-11 | Sekisui Chem Co Ltd | Resin composition comprising benzoxadine ring-containing thermosetting resin |
| US11124608B2 (en) * | 2018-04-04 | 2021-09-21 | Case Western Reserve University | Polybenzoxazine resins with high hydrogen content, and composites therefrom |
| WO2020054218A1 (en) * | 2018-09-14 | 2020-03-19 | 積水化学工業株式会社 | Benzoxazine compound, curable resin composition, adhesive, adhesive film, cured object, circuit board, interlayer dielectric material, and multilayered printed wiring board |
| CN112533906A (en) * | 2018-09-14 | 2021-03-19 | 积水化学工业株式会社 | Benzoxazine compound, curable resin composition, adhesive film, cured product, circuit board, interlayer insulating material, and multilayer printed wiring board |
| JPWO2020054218A1 (en) * | 2018-09-14 | 2021-08-30 | 積水化学工業株式会社 | Benzoxazine compounds, curable resin compositions, adhesives, adhesive films, cured products, circuit boards, interlayer insulating materials, and multilayer printed wiring boards |
| JP7474054B2 (en) | 2018-09-14 | 2024-04-24 | 積水化学工業株式会社 | Benzoxazine compound, curable resin composition, adhesive, adhesive film, cured product, circuit board, interlayer insulating material, and multilayer printed wiring board |
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