JPH01158037A - Production of polyazomethyne - Google Patents
Production of polyazomethyneInfo
- Publication number
- JPH01158037A JPH01158037A JP22884387A JP22884387A JPH01158037A JP H01158037 A JPH01158037 A JP H01158037A JP 22884387 A JP22884387 A JP 22884387A JP 22884387 A JP22884387 A JP 22884387A JP H01158037 A JPH01158037 A JP H01158037A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- polyazomethine
- represented
- group
- diketone
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 125000005594 diketone group Chemical group 0.000 claims abstract description 7
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 4
- 229920000343 polyazomethine Polymers 0.000 claims description 14
- 150000004985 diamines Chemical class 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000006068 polycondensation reaction Methods 0.000 abstract description 6
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 abstract description 2
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 abstract description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000005266 casting Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- -1 aromatic Schiff base Chemical class 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
- 229960003986 tuaminoheptane Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Description
【発明の詳細な説明】
人、産業上の利用分野
本発明は耐熱性に優れた、しかも成形性の改善されたポ
リアゾメチンの製造法である。DETAILED DESCRIPTION OF THE INVENTION Human and Industrial Fields of Use The present invention is a method for producing polyazomethine having excellent heat resistance and improved moldability.
Ｂ、従来の技術
芳香族ポリアゾメチンは、耐Ｍ性尋電気的・機械的性質
表どの点から興味ある高分子と考えられ、また一方にお
いてジアミンとジアルデヒドから脱水によって得られる
簡単な構造単位から構成されているなどの理由からポリ
アゾメチン合成の各種の方法が試みられている（たとえ
ば特開昭５１−１３８８００号、同５９−１１３０３３
号）。B. Prior Art Aromatic polyazomethine is considered to be an interesting polymer due to its M resistance, electrical and mechanical properties, and on the other hand, it is a simple structural unit obtained from diamines and dialdehydes by dehydration. Various methods for synthesizing polyazomethine have been attempted for reasons such as the structure of
issue).
しかしガから芳香族高分子に共通にみられる慇点、す彦
わち重合反応の初期段階で溶媒不溶となり系外に沈澱し
、高分子量に成長せず、また不融であるため、その成形
、成膜性に雑煮がある。However, there is a point commonly found in aromatic polymers, that is, they become insoluble in the solvent at the initial stage of the polymerization reaction, precipitate out of the system, do not grow to a high molecular weight, and are infusible, so their formation , there is a problem with film forming properties.
Ｃ０発明が解決しようとする問題点 本発明はその成形、成膜性を改善したものである。Problems that C0 invention attempts to solve The present invention improves the molding and film forming properties.
Ｄ０問題点を解決するための手段
本発明は下記（１）式で示されるテトラシリルジアミン
と（ＩＩ）式で示されるジアルデヒドまたはジケトンを
重縮合することを特徴とするポリアゾメチンの製造法で
ある。Means for solving the D0 problem The present invention is a method for producing polyazomethine, which is characterized by polycondensing a tetrasilyl diamine represented by the following formula (1) and a dialdehyde or diketone represented by the formula (II). be.
（Ｒ”５Ｓｉ） Ｎ−Ｘ−Ｎ（ＳｉＲ２３）
・・・・・・・・・（１）（１）式で示されるテトラシ
リルジアミンと（ＩＩ）式で示されるジアルデヒドま九
はジケトンの重縮合は溶媒中３０〜２００℃、３〜６時
間の条件下で行なわれる。(R”5Si) N-X-N(SiR23)
・・・・・・・・・(1) The polycondensation of the tetrasilyl diamine represented by the formula (1) and the dialdehyde or diketone represented by the formula (II) is carried out in a solvent at 30 to 200°C, 3 to 6 It is carried out under the conditions of time.
ここで溶媒としては、代表的にはＮ−メチル−２−ピロ
リドン（ＮＭＰ）が用いられ、七ツマー濃度は１０ Ｍ
４〜５０−ｍチである。さらＫこの反応蜂
は無触媒下で行なわれる。Here, N-methyl-2-pyrrolidone (NMP) is typically used as the solvent, and the heptamine concentration is 10 M.
It is 4 to 50 meters long. Furthermore, this reaction is carried out without a catalyst.
このようにして得られた粘性ある液体を、反応生成物を
再沈澱することなく、ガラス板上にキャストし、溶媒を
加熱除去することによシガラス板よシ剥離させ、強靭な
耐熱性にすぐれたポリアゾメチンフィルムを得ることが
できる。The viscous liquid obtained in this way is cast onto a glass plate without re-precipitating the reaction product, and the solvent is removed by heating to peel off the glass plate. A polyazomethine film can be obtained.
前記（Ｉ）で示されるテトラシリルジアミンのＸ１Ｒ１
、Ｒ２の代表的な例としては次のようなものがあげられ
る。X1R1 of the tetrasilyldiamine represented by (I) above
, R2 include the following.
＋５０２Ｋ）、（）（Ｘ なる群から選ばれ１歇
Ｒ１％Ｒ２は炭素纂子１〜１０の低級アルキル基（メチ
ル−、エチル７、プロピル−、ペンチル−ナトの直鎖状
または分岐状アルキル基）なる群から選ばれる。+502K), ( ) ( ) is selected from the group.
また前記（Ｉｔ）で示されるジアルデヒドまたはジケト
ンの７％Ｒ３、Ｒ４の代表的な例としては次のよう表も
のがあげられる。Further, as representative examples of 7% R3 and R4 of the dialdehyde or diketone represented by (It) above, the following table may be mentioned.
（とＨ・舎・（）０舎ｏ（Ｘ・
杖
なる群から選ばれ １３ 、Ｒ４は、水素原子、炭素原
÷１〜１０の低級アルキル基（メチル−、エチル−、プ
ロピル−、ペンチル−などの直鎖状または分岐状アルキ
ル基）なる群から選ばれる。selected from the group consisting of (and (straight-chain or branched alkyl groups).
（Ｉ）および（Ｉｔ）を重縮合、あるいはさらに重縮合
後キャストなどして得られるポリアゾメチンはこの反応
途中では、ポリアゾメチンの前駆体である、溶媒可溶性
の中間体が生成している可能性が大きい。この前駆体は
、キャスト、加熱することにより、アゾメチン基に化学
変化し、溶媒不溶のポリアゾメチン成形体を得る。Polyazomethine obtained by polycondensation of (I) and (It) or casting after further polycondensation may generate a solvent-soluble intermediate, which is a precursor of polyazomethine, during this reaction. is large. This precursor is chemically changed into an azomethine group by casting and heating to obtain a solvent-insoluble polyazomethine molded article.
前記（１）および（ＩＩ）中のＸ、Ｙは−または二以上
の炭素環式六員環基、とくに芳香環基であるが、該環基
の水素原子はアルキル基、アリール基、アラルキル基、
ハロゲン基、ニトロ基などの官能基によって置換されて
いてもよい。また該環基の炭素原子は窒素表どによって
置換されていてもよい。In (1) and (II) above, X and Y are - or two or more carbocyclic six-membered ring groups, especially aromatic ring groups, and the hydrogen atom of the ring group is an alkyl group, aryl group, aralkyl group. ,
It may be substituted with a functional group such as a halogen group or a nitro group. Further, the carbon atoms of the ring group may be substituted with a nitrogen group or the like.
また芳香環基はオルト、メタ、パラの位置で結合される
が、通常はメタ、パラが多い。炭素環式六員環基、とく
に芳香環基が二基上存在する場合のそれぞれの基を結ぶ
基、す珍わち一＠−＠で表わされる式中のＺは÷ＣＨ２
＋ｍで示されるアルキレン基、酸素原子、あるいは酸素
、窒素、硫黄などを有する基であってもよいし、また場
合によっては２はなくてもよい。また芳香環基は締金環
式芳香族炭化水素基であってもよい。Further, aromatic ring groups are bonded at the ortho, meta, and para positions, but usually the meta and para positions are more common. A carbocyclic six-membered ring group, especially a group connecting each group when two or more aromatic ring groups are present, that is, Z in the formula represented by 1@-@ is ÷CH2
It may be an alkylene group represented by +m, an oxygen atom, or a group containing oxygen, nitrogen, sulfur, etc., and 2 may be omitted depending on the case. Further, the aromatic ring group may be a clamped ring type aromatic hydrocarbon group.
本発明によ如得られるポリアゾメチンは芳香族シッフベ
ースを含む高分子であシ、耐熱性に優れ、さらに成形性
が改善されているが、重縮合にあたっては前記（１）、
（ＩＩ）成分に加えて、他の重縮合成分を、本発明の目
的が阻害されない程度に使用することは自由である。The polyazomethine obtained according to the present invention is a polymer containing an aromatic Schiff base, has excellent heat resistance, and has improved moldability.
In addition to component (II), other polycondensation components may be used freely to the extent that the object of the present invention is not impaired.
本発明においては前記（１）、 （ＩＩ）成分を！縮
合して得た粘性の液体からキャストなどによシ成形体を
得るが、ここで成形体とはフィルム、繊維、シート、板
、棒などある。これらの成形体は耐熱性、電気的適性、
さらには機械的適性の要求される用途に使用される。In the present invention, the above (1) and (II) components are used! A molded product is obtained by casting or the like from the viscous liquid obtained by condensation, and the molded product here includes films, fibers, sheets, plates, rods, etc. These molded bodies have high heat resistance, electrical suitability,
Furthermore, it is used in applications requiring mechanical aptitude.
次に実施例によシ本発明をさらに説明する。Next, the present invention will be further explained with reference to Examples.
Ｆ、実施例
実施例１〜５
ルシリル）ジアミンに溶媒としてテトラヒドロフラン（
ＴＨＦ）を用い、２．５当量の臭化エチルマグネシウム
（ＥｔＭｇＢｒ）と３時間、窒素気流で還流した。その
後、３当量のトリメチルクロロシラン（（ＣＨ３）３５
ｔＣＩりを加え、さらに４時間還流した。F, Examples Examples 1 to 5 Tetrahydrofuran (
THF) and refluxed with 2.5 equivalents of ethylmagnesium bromide (EtMgBr) for 3 hours in a nitrogen stream. Thereafter, 3 equivalents of trimethylchlorosilane ((CH3)35
tCI was added and the mixture was refluxed for an additional 4 hours.
反応終了後、室温でしばらく放置し、Ｍｇｃｌ！Ｂｒを
析出させた。それをＦ別し、ｐ液を濃縮し、減圧蒸留を
し、生成物を得た。さらにＮ、Ｎ−ジメチルホルムアミ
ド（ＤＭＦ）に、！ニジ再結晶し、精製することによシ
、目的のＮ、Ｎ、Ｎ’、Ｎ’−テトラ（トリメチルシリ
ル）ジアミンを得た。After the reaction is completed, leave it for a while at room temperature, then Mgcl! Br was precipitated. It was separated by F, and the p liquid was concentrated and distilled under reduced pressure to obtain a product. Furthermore, to N,N-dimethylformamide (DMF),! The desired N,N,N',N'-tetra(trimethylsilyl)diamine was obtained by di-recrystallization and purification.
ここでＸとしては次のものを使用した。Here, the following was used as X.
以下余白
Ｎ、 Ｎ、 Ｎ’、 Ｎ’ テトラ（トリメチルシリル
）ジアミン（０，００５モル）とフタルアルデヒド（０
，００５モル）を当量混合し溶媒としてＮＭＰ−水素（
ＮＭＰ ： Ｈ２０＝ ９８ ： ２ （重ｉｉ′チ）
）１０＋ｚ／で窒素雰囲気下、３０°Ｃ１４８時間反応
させ、その後さらにＮＭＰに対し約５％の水を加えたも
の（ＮＭＰ ： Ｈ２０中９３ニア （重量％））を遣
流し、３０分反応させた。その反応溶液をガラス板上に
キャストし、１００℃で乾燥することによりポリアゾメ
チンフィルムを得た。これを図式で表わすと次のとおシ
となる。Below are blank spaces N, N, N', N' tetra(trimethylsilyl)diamine (0,005 mol) and phthalaldehyde (0
,005 mol) were mixed in equivalent amounts and NMP-hydrogen (
NMP: H20 = 98: 2 (heavy ii'ch)
) 10+z/ in a nitrogen atmosphere at 30°C for 148 hours, and then a mixture of NMP and approximately 5% water (NMP: 93 nia (wt%) in H20) was poured in and reacted for 30 minutes. . The reaction solution was cast on a glass plate and dried at 100°C to obtain a polyazomethine film. This can be expressed graphically as follows.
ＮＭＰ −Ｈ２０／３０℃、４８時間−ＮＭＰ−８２０
／還流０．５時間結果を表１に示す。NMP-H20/30°C, 48 hours-NMP-820
/Reflux for 0.5 hours The results are shown in Table 1.
工
なお実施例２で得られた重合体のσＲスペクトルを図１
に示すが、それによシその重合体がポリ（ｍ−キンリリ
テンーｍ−）ユニレンジアミン）であることが確認され
た。Figure 1 shows the σR spectrum of the polymer obtained in Example 2.
However, it was confirmed that the polymer was poly(m-quinryritene-m-)unilene diamine).
また各実施例で得られている重合体は溶剤可溶性中間体
を経由していると考えられる。Furthermore, it is thought that the polymers obtained in each example were produced via a solvent-soluble intermediate.
以下余白
Ｇ０発明の効果
本発明により、成形性の改善されたポリアゾメチンを得
ることができる。したがってポリアゾメチンが本来有し
ている優れた耐熱性、機械的性質に加え、優れた成形性
を併せ有することになったので、今後耐熱性、機械的性
質の要求される分野において多いに期待できる。Margin G0 Below Effects of the Invention According to the present invention, polyazomethine with improved moldability can be obtained. Therefore, in addition to the excellent heat resistance and mechanical properties that polyazomethine inherently possesses, it also has excellent moldability, so it can be expected to be used in many fields that require heat resistance and mechanical properties in the future. .
添付図面は、実施例２で得られたポリマーフィルムの赤
外吸収スペクトルである。
特許出願人 株式会社 り ラ しThe attached drawing is an infrared absorption spectrum of the polymer film obtained in Example 2. Patent applicant RiRa Shi Co., Ltd.
Claims (2)
と（II）式で示されるジアルデヒドまたはジケトンを重
縮合することを特徴とするポリアゾメチンの製造法。 （Ｒ＾１＿３Ｓｉ）＿２Ｎ−Ｘ−Ｎ（ＳｉＲ＾２＿３）
＿２………（ I ）▲数式、化学式、表等があります▼
………（II） 〔ＸおよびＹは一以上の炭素環式六員環基であり、Ｘお
よびＹは同一または異なる基で ある。Ｒ＾１およびＲ＾２は低級アルキル基であり、Ｒ
＾１およびＲ＾２は同一または異なる基である。 Ｒ＾３およびＲ＾４は水素または低級アルキル基であり
、Ｒ＾３およびＲ＾４は同一または異なる基である。〕(1) A method for producing polyazomethine, which comprises polycondensing a tetrasilyl diamine represented by the following formula (I) and a dialdehyde or diketone represented by the formula (II). (R^1_3Si)_2N-X-N(SiR^2_3)
＿２……(I)▲There are mathematical formulas, chemical formulas, tables, etc.▼
......(II) [X and Y are one or more carbocyclic six-membered ring groups, and X and Y are the same or different groups. R^1 and R^2 are lower alkyl groups, R
^1 and R^2 are the same or different groups. R^3 and R^4 are hydrogen or lower alkyl groups, and R^3 and R^4 are the same or different groups. ]
II）式で示されるジアルデヒドまたはジケトンを溶媒中
、３０〜２００℃、３〜６時間重縮合する特許請求の範
囲第１項記載のポリアゾメチンの製造法。(2) Tetrasilyldiamine represented by the formula (I) and (
The method for producing polyazomethine according to claim 1, wherein the dialdehyde or diketone represented by formula II) is polycondensed in a solvent at 30 to 200°C for 3 to 6 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22884387A JPH01158037A (en) | 1987-09-11 | 1987-09-11 | Production of polyazomethyne |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22884387A JPH01158037A (en) | 1987-09-11 | 1987-09-11 | Production of polyazomethyne |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01158037A true JPH01158037A (en) | 1989-06-21 |
Family
ID=16882734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22884387A Pending JPH01158037A (en) | 1987-09-11 | 1987-09-11 | Production of polyazomethyne |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01158037A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009179747A (en) * | 2008-01-31 | 2009-08-13 | Sekisui Chem Co Ltd | New azomethine composition, its molded article, and electronic device containing it |
| WO2014084310A1 (en) * | 2012-11-28 | 2014-06-05 | 日立化成株式会社 | Amino-modified siloxane compound, modified imide resin, thermosetting resin composition, prepreg, resin-equipped film, laminated plate, multilayer printed circuit board, and semiconductor package |
-
1987
- 1987-09-11 JP JP22884387A patent/JPH01158037A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009179747A (en) * | 2008-01-31 | 2009-08-13 | Sekisui Chem Co Ltd | New azomethine composition, its molded article, and electronic device containing it |
| WO2014084310A1 (en) * | 2012-11-28 | 2014-06-05 | 日立化成株式会社 | Amino-modified siloxane compound, modified imide resin, thermosetting resin composition, prepreg, resin-equipped film, laminated plate, multilayer printed circuit board, and semiconductor package |
| JPWO2014084310A1 (en) * | 2012-11-28 | 2017-01-05 | 日立化成株式会社 | Amino-modified siloxane compound, modified imide resin, thermosetting resin composition, prepreg, film with resin, laminate, multilayer printed wiring board, and semiconductor package |
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