JPH0413751A - Thermosetting resin composition - Google Patents
Thermosetting resin compositionInfo
- Publication number
- JPH0413751A JPH0413751A JP11690590A JP11690590A JPH0413751A JP H0413751 A JPH0413751 A JP H0413751A JP 11690590 A JP11690590 A JP 11690590A JP 11690590 A JP11690590 A JP 11690590A JP H0413751 A JPH0413751 A JP H0413751A
- Authority
- JP
- Japan
- Prior art keywords
- composition
- heat
- hexamethylenetetramine
- resin
- formula
- 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.)
- Pending
Links
- 239000011342 resin composition Substances 0.000 title claims description 6
- 229920001187 thermosetting polymer Polymers 0.000 title claims description 6
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 229920005989 resin Polymers 0.000 claims abstract description 13
- 239000011347 resin Substances 0.000 claims abstract description 13
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 3
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 abstract description 16
- 235000010299 hexamethylene tetramine Nutrition 0.000 abstract description 8
- 239000004312 hexamethylene tetramine Substances 0.000 abstract description 8
- HRDCVMSNCBAMAM-UHFFFAOYSA-N 3-prop-2-ynoxyprop-1-yne Chemical compound C#CCOCC#C HRDCVMSNCBAMAM-UHFFFAOYSA-N 0.000 abstract description 3
- 150000002989 phenols Chemical class 0.000 abstract description 2
- 230000015556 catabolic process Effects 0.000 abstract 1
- 238000013329 compounding Methods 0.000 abstract 1
- 238000006731 degradation reaction Methods 0.000 abstract 1
- 230000006866 deterioration Effects 0.000 description 8
- 239000012778 molding material Substances 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000005011 phenolic resin Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229920006026 co-polymeric resin Polymers 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- UPSAJWJCXXNGQR-UHFFFAOYSA-N 2-ethenylphenol;styrene Chemical compound C=CC1=CC=CC=C1.OC1=CC=CC=C1C=C UPSAJWJCXXNGQR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229920006272 aromatic hydrocarbon resin Polymers 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- 229920003261 Durez Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、寸法変化率が小さく、耐熱劣化性、靭性に優
れた耐熱成形材料用の熱硬化性樹脂組成物に関するもの
である。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a thermosetting resin composition for a heat-resistant molding material that has a small dimensional change rate, excellent heat deterioration resistance, and toughness.
（従来技術）
自動車部品、モータ一部品などの耐熱性が要求される分
野に、フェノール樹脂成形材料が使われている。しかし
年々耐熱性の要求が向上し、更に高耐熱で靭性に優れた
成形材料用樹脂の開発が強く望まれている。フェノール
樹脂は、数秒から数時間の短期耐熱性については非常に
優れているが、熱酸化を受は易いフェノール性水酸基を
有することと、硬化時に多量の揮発分が発生し、この一
部が成形品中に残存することのために、高温下では寸法
変化率が大きく、熱劣化し、脆いという欠点がある。(Prior Art) Phenol resin molding materials are used in fields that require heat resistance, such as automobile parts and motor parts. However, the requirements for heat resistance are increasing year by year, and there is a strong desire to develop resins for molding materials that have even higher heat resistance and excellent toughness. Phenolic resin has excellent short-term heat resistance from several seconds to several hours, but it has phenolic hydroxyl groups that are easily susceptible to thermal oxidation, and a large amount of volatile matter is generated during curing, and some of this is difficult to mold. Because it remains in the product, it has the drawbacks of large dimensional change rate, thermal deterioration, and brittleness at high temperatures.
ｄ、ｅ、ｆは各組成の百分率を示す。）（Ｂ）へキサメ
チレンテトラミンとを含有することを特徴とする熱硬化
性樹脂組成物である・（作用）
本発明において用いられるプロパルギルエーテル化樹脂
は、フェノール性水酸基を有する樹脂、具体的にはフェ
ノール樹脂、フェノール・芳香族炭化水素樹脂、例えば
フェノール変性キシレン樹脂（三菱瓦斯化学■製二カノ
ールＰ−１圓など）やフェノールアラルキル樹脂（三井
東圧■製ミレツクスＸＬ−２２５など）、ビニルフェノ
ール善石油化学■製マルカリンカーＭなど）又はビニル
フェノール・スチレン共重合樹脂（丸善石油化学■製マ
ル力ゾン゛カーＣＳＴなど）を、塩化プロパルギル又は
臭化プロパルギルと反応させ，、プロパルギルエーテル
化したもので、下記式〔Ｉ〕又は（ Ｉｔ ）の組成で
示されるものである。d, e, f indicate the percentage of each composition. ) (B) Hexamethylenetetramine. (Function) The propargyl etherified resin used in the present invention is a resin having a phenolic hydroxyl group, specifically are phenol resins, phenol/aromatic hydrocarbon resins, such as phenol-modified xylene resins (Mitsubishi Gas Chemical Co., Ltd.'s Nikanol P-1 En, etc.), phenol aralkyl resins (Mitsui Toatsu Co., Ltd.'s Millex XL-225, etc.), vinyl phenol. Products made by reacting vinylphenol-styrene copolymer resins (such as Maruka Linker M manufactured by Zen Petrochemical ■) or vinylphenol-styrene copolymer resin (Marukisoncar CST manufactured by Maruzen Petrochemical ■) with propargyl chloride or propargyl bromide to form propargyl ethers. It is represented by the composition of the following formula [I] or (It).
（発明が解決しようとする課題）
本発明の目的とするところは、硬化性が良好で成形品の
寸法変化率が小さく、耐熱劣化性、靭性に，優れた熱硬
化性樹脂組成物を提供するにある。(Problems to be Solved by the Invention) An object of the present invention is to provide a thermosetting resin composition that has good curability, a small dimensional change rate of molded products, and excellent heat deterioration resistance and toughness. It is in.
（課題を解決するための手段）
本発明は、
（１）（Ａ）下記式（１）又は／及び下記式（ ＩＩ
）の組成で示されるプロパルギルエーテル化樹脂と、（
Ｒ１ ニーＨ又は−ＣＨ３の中からそれぞれ独立に選
択された基
０＜ａ，ｂ＜１００、０≦Ｃ ＜ １００かつａ＋ｂ＋
ｃ：４００ｔ３−、ｂ，ｃは各組成の百分率を示す。）
（０＜ ｄ 、ｅ ＜ １００、０≦ｆ＜１００かツｄ
＋ｅ＋ｆ＝１００
（ＲエニーＨ又は−ＣＨ３の中からそれぞれ独立に選択
された基）
ａ，ｂ，ｃ及びｄ，ｅ，ｆは、それぞれ〔Ｉ〕及び（
ＩＩ ）式における各組成の百分率（％）を示し、樹脂
中にそれぞれの構造をもつ部分が全体として〔Ｉ〕式で
はａ，ｂ，ｃ、（ ＩＩ ）式ではｄ。(Means for Solving the Problems) The present invention provides (1) (A) the following formula (1) or/and the following formula (II
) and a propargyl etherified resin shown in the composition (
R1 Groups independently selected from among H or -CH3 0<a, b<100, 0≦C<100 and a+b+
c: 400t3-, b and c indicate the percentage of each composition. )
(0<d, e<100, 0≦f<100 or d
+e+f=100 (groups independently selected from R any H or -CH3) a, b, c and d, e, f are [I] and (
The percentage (%) of each composition in formula II) is shown, and the parts with each structure in the resin are a, b, and c in formula [I], and d in formula (II).
ｅ．ｆの比で存在しているものである。そして、０＜ａ
，ｂ＜ｔｏｏ、０≦ｃ ＜ １００か”）ａ＋ｂ＋ｃ＝
１０００＜ ｄ 、ｅ ＜ １００、０≦ｆ ＜ １０
０かッｄ＋ｅ＋ｆ＝１００である。好ましくは、２０≦
ａ，ｂ，ｄ，ｅ≦６０、０≦ｃ，ｆ≦６０が良い。e. It exists in the ratio of f. And 0<a
, b<too, 0≦c<100?”) a+b+c=
1000<d, e<100, 0≦f<10
0kd+e+f=100. Preferably 20≦
a, b, d, e≦60, 0≦c, f≦60.
ａ又はｄ成分は、耐熱寸法安定性、耐熱劣化性、及び靭
性の向上に効果があり、少な過ぎると上記の特性が低下
する。また多過ぎると、硬化性が悪化し、熱剛性が下が
る。Component a or d is effective in improving heat-resistant dimensional stability, heat-resistant deterioration resistance, and toughness, and if it is too small, the above properties will deteriorate. On the other hand, if the amount is too large, curing properties will deteriorate and thermal rigidity will decrease.
ｂ又はｅ成分は、ヘキサメチレンテトラミンと反応して
、硬化性、熱剛性に寄与する。多過ぎると耐熱寸法安定
性、耐熱劣化性及び靭性が向上しない。Component b or e reacts with hexamethylenetetramine and contributes to curability and thermal rigidity. If it is too large, heat-resistant dimensional stability, heat-resistant deterioration resistance, and toughness will not improve.
Ｃ又はｆ成分は、耐熱寸法安定性、耐熱劣化性と共に耐
水性の向上に効果がある。しかし多過ぎると、硬化性、
熱剛性が大幅に低下する。The C or f component is effective in improving heat-resistant dimensional stability, heat-resistant deterioration resistance, and water resistance. However, if there is too much, hardening,
Thermal stiffness is significantly reduced.
本発明において用いられるヘキサメチレンテトラミンは
、通常フェノールノボラックの硬化剤に用いられるもの
でよい。ヘキサメチレンテトラミンの量は、ｂ又はｅ成
分であるフェノール核１当量に対し、０．０３〜０．３
当量が好ましい。少な過ぎると、硬化性、熱剛性が低下
し、多過ぎると揮発分が多くなって、耐熱寸法安定性、
耐熱劣化性が悪化する。The hexamethylenetetramine used in the present invention may be one commonly used as a curing agent for phenol novolak. The amount of hexamethylenetetramine is 0.03 to 0.3 per equivalent of phenol nucleus as component b or e.
Equivalent amounts are preferred. If the amount is too low, curability and thermal rigidity will decrease, and if it is too high, the volatile content will increase, resulting in poor heat-resistant dimensional stability,
Heat deterioration resistance deteriorates.
本発明の熱硬化性樹脂組成物は、硬化促進剤、充填剤、
滑剤、離型剤、シランカップリング剤等を適宜配合添加
し、加熱混練することによって成形材料にすることがで
きる。The thermosetting resin composition of the present invention includes a curing accelerator, a filler,
A molding material can be obtained by appropriately mixing and adding a lubricant, a mold release agent, a silane coupling agent, etc., and then heating and kneading the mixture.
（実施例）
［プロパルギルエーテル化樹脂の合成］合成例１〜３
撹拌装置、還流冷却器、温度計及び滴下ロートを付けた
反応容器に、第１表の処方に従って、水酸化カリウムと
、水／アセトン（１／１ ）の混合溶媒を入れて溶解さ
せ、これにフェノール・芳香族炭化水素樹脂、ビニルフ
ェノール・スチレン共重合樹脂又はフェノール樹脂を添
加し、溶解させた。(Example) [Synthesis of propargyl etherified resin] Synthesis Examples 1 to 3 Into a reaction vessel equipped with a stirring device, a reflux condenser, a thermometer, and a dropping funnel, potassium hydroxide and water/ A mixed solvent of acetone (1/1) was added and dissolved, and a phenol/aromatic hydrocarbon resin, vinylphenol/styrene copolymer resin, or phenol resin was added and dissolved.
この溶液を加熱し、塩化プロパルギルを滴下して、還流
下２時間反応させた。その後、塩酸で中和して、アセト
ンと未反応の塩化プロパルギルを留去し、トルエン１リ
ツトルを添加した。分液ロートに移し、水洗を３回行い
、エバポレーターで溶媒を除去した。This solution was heated, propargyl chloride was added dropwise, and the mixture was reacted under reflux for 2 hours. Thereafter, the mixture was neutralized with hydrochloric acid to distill off unreacted propargyl chloride with acetone, and 1 liter of toluene was added. The mixture was transferred to a separating funnel, washed with water three times, and the solvent was removed using an evaporator.
得られた樹脂のプロパルギルエーテル化率（フェノール
性水酸基の反応率）を第１表に示した。Table 1 shows the propargyl etherification rate (reaction rate of phenolic hydroxyl groups) of the obtained resin.
実施例１〜３
合成例１〜３で得たプロパルギルエーテル化樹脂に、第
２表に示すように、ヘキサメチレンテトラミン、硬化促
進剤（酸化マグネシウム）、ガラス繊維、ステアリン酸
及びアミノシランを配合し、熱ロールで混練して成形材
料を得た。得られた成形材料は１７０°Ｃ３分で成形し
た。この成形品を更に１８０℃８時間後硬化を行い、特
性を評価した。Examples 1 to 3 The propargyl etherified resin obtained in Synthesis Examples 1 to 3 was blended with hexamethylenetetramine, a curing accelerator (magnesium oxide), glass fiber, stearic acid, and aminosilane, as shown in Table 2. A molding material was obtained by kneading with hot rolls. The obtained molding material was molded at 170°C for 3 minutes. This molded article was further cured at 180° C. for 8 hours, and its properties were evaluated.
結果を第２表に示す。The results are shown in Table 2.
実施例１〜３は、硬化性が良好で、破壊エネルギーが大
きく、高温熱処理での曲げ強度保持率、寸法安定性、重
量変化率が向上している。Examples 1 to 3 have good curability, large fracture energy, and improved bending strength retention, dimensional stability, and weight change rate during high-temperature heat treatment.
比較例１
ヘキサメチレンテトラミンを加えずに、他は実施例１と
同様に行ったものである。硬化性が悪く、成形品が得ら
れなかった。Comparative Example 1 The same procedure as in Example 1 was carried out except that hexamethylenetetramine was not added. Curability was poor and no molded product could be obtained.
比較例２
プロパルギルエーテル化樹脂に代えてフェノール・ノボ
ラック樹脂を用い、実施例１と同様に行ったものである
。破壊エネルギーが小さく、吸水率が大きく、また高温
熱処理での曲げ強度保持率が小さく、寸法変化率、重量
変化率が大きく、良好な成形品が得られなかった。Comparative Example 2 The same procedure as in Example 1 was carried out using a phenol novolac resin in place of the propargyl etherified resin. The fracture energy was low, the water absorption rate was high, the bending strength retention rate during high-temperature heat treatment was low, the dimensional change rate and weight change rate were large, and a good molded product could not be obtained.
（発明の効果）
本発明の熱硬化性樹脂組成物は、硬化性が良好で、これ
を用いた成形品は靭性に富み、耐熱寸法安定性、耐熱劣
化性に優れているので、高耐熱が要求されるコンミテー
タ、ブレーキピストンなどの成形材料用として好適であ
る。(Effects of the Invention) The thermosetting resin composition of the present invention has good curability, and molded products using it have high toughness, excellent heat-resistant dimensional stability, and heat-resistant deterioration resistance, so they have high heat resistance. Suitable for molding materials such as commutators and brake pistons.
第１表 （注）＊１：三菱瓦斯化学■製 ＊２：丸善石油化学■製 ＊３：住人デュレズ■製 二カノールＰ−１００ マルカリン力−Ｍ ＰＲ−５１４７０ 手続補正書 平成２年Table 1 (Note) *1: Manufactured by Mitsubishi Gas Chemical ■ *2: Manufactured by Maruzen Petrochemical *3: Made by Resident Durez ■ Nikanol P-100 Markarin Power-M PR-51470 Procedural amendment 1990
Claims (1)
組成で示されるプロパルギルエーテル化樹脂と▲数式、
化学式、表等があります▼・・・〔 I 〕 （Ｒ＿１：−Ｈ又は−ＣＨ＿３の中からそれぞれ独立に
選択された基 ０＜ａ、ｂ＜１００、０≦ｃ＜１００かつａ＋ｂ＋ｃ＝
１００ａ、ｂ、ｃは各組成の百分率を示す。） ▲数式、化学式、表等があります▼〔II〕 （０＜ｄ、ｅ＜１００、０≦ｆ＜１００ かつｄ＋ｅ＋ｆ＝１００ ｄ、ｅ、ｆは各組成の百分率を示す。） （Ｂ）ヘキサメチレンテトラミンとを含有することを特
徴とする熱硬化性樹脂組成物。(1) (A) A propargyl etherified resin represented by the following formula [I] or/and the following formula [II] and the formula ▲,
There are chemical formulas, tables, etc.
100a, b, and c indicate the percentage of each composition. ) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [II] (0<d, e<100, 0≦f<100 and d+e+f=100 d, e, f indicate the percentage of each composition.) (B) Hexa A thermosetting resin composition characterized by containing methylenetetramine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11690590A JPH0413751A (en) | 1990-05-08 | 1990-05-08 | Thermosetting resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11690590A JPH0413751A (en) | 1990-05-08 | 1990-05-08 | Thermosetting resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0413751A true JPH0413751A (en) | 1992-01-17 |
Family
ID=14698546
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11690590A Pending JPH0413751A (en) | 1990-05-08 | 1990-05-08 | Thermosetting resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0413751A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2020175537A1 (en) * | 2019-02-28 | 2020-09-03 |
-
1990
- 1990-05-08 JP JP11690590A patent/JPH0413751A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2020175537A1 (en) * | 2019-02-28 | 2020-09-03 | ||
| WO2020175537A1 (en) * | 2019-02-28 | 2020-09-03 | 三菱瓦斯化学株式会社 | Resin composition, prepreg, metal foil-clad laminate board, resin composite sheet, and, printed circuit board |
| CN113490715A (en) * | 2019-02-28 | 2021-10-08 | 三菱瓦斯化学株式会社 | Resin composition, prepreg, metal foil-clad laminate, resin composite sheet, and printed wiring board |
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