JPH02207087A - Epoxy-group-containing silane compound - Google Patents
Epoxy-group-containing silane compoundInfo
- Publication number
- JPH02207087A JPH02207087A JP2809689A JP2809689A JPH02207087A JP H02207087 A JPH02207087 A JP H02207087A JP 2809689 A JP2809689 A JP 2809689A JP 2809689 A JP2809689 A JP 2809689A JP H02207087 A JPH02207087 A JP H02207087A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy
- group
- expressed
- formula
- epoxynorbornen
- 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
- -1 silane compound Chemical class 0.000 title claims abstract description 20
- 125000003700 epoxy group Chemical group 0.000 title claims description 10
- 229910000077 silane Inorganic materials 0.000 title claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 12
- LSIGXJYVSGAHHA-UHFFFAOYSA-N 6-ethenyl-3-oxatricyclo[3.2.1.02,4]oct-2(4)-ene Chemical compound C=CC1CC2C(O3)=C3C1C2 LSIGXJYVSGAHHA-UHFFFAOYSA-N 0.000 abstract description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract description 4
- 239000000853 adhesive Substances 0.000 abstract description 3
- 230000001070 adhesive effect Effects 0.000 abstract description 3
- 239000000956 alloy Substances 0.000 abstract description 3
- 229910045601 alloy Inorganic materials 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 3
- 239000012778 molding material Substances 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 abstract description 3
- 239000003566 sealing material Substances 0.000 abstract description 3
- 239000003381 stabilizer Substances 0.000 abstract description 3
- 229920003002 synthetic resin Polymers 0.000 abstract description 3
- 239000000057 synthetic resin Substances 0.000 abstract description 3
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 abstract description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract description 2
- 229910010272 inorganic material Inorganic materials 0.000 abstract description 2
- 239000011147 inorganic material Substances 0.000 abstract description 2
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000004593 Epoxy Substances 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012263 liquid product Substances 0.000 description 3
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 3
- CABDEMAGSHRORS-UHFFFAOYSA-N oxirane;hydrate Chemical compound O.C1CO1 CABDEMAGSHRORS-UHFFFAOYSA-N 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- DRUOQOFQRYFQGB-UHFFFAOYSA-N ethoxy(dimethyl)silicon Chemical compound CCO[Si](C)C DRUOQOFQRYFQGB-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- VAMFXQBUQXONLZ-UHFFFAOYSA-N icos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000006884 silylation reaction Methods 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 1
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- RSIHJDGMBDPTIM-UHFFFAOYSA-N ethoxy(trimethyl)silane Chemical compound CCO[Si](C)(C)C RSIHJDGMBDPTIM-UHFFFAOYSA-N 0.000 description 1
- XWRLQRLQUKZEEU-UHFFFAOYSA-N ethyl(hydroxy)silicon Chemical compound CC[Si]O XWRLQRLQUKZEEU-UHFFFAOYSA-N 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000005048 methyldichlorosilane Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadecene Natural products CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004381 surface treatment Methods 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
- 238000005829 trimerization reaction Methods 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
- Silicon Polymers (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、特定のエポキシ基含有シラン化合物に関し、
詳しくは、２−（２，３−エポキシノルボルネン−５−
イル）エチル基を有するオリゴまたはポリシロキサン化
合物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a specific epoxy group-containing silane compound,
Specifically, 2-(2,3-epoxynorbornene-5-
The present invention relates to oligo- or polysiloxane compounds having ethyl groups.
エポキシ化合物、特に１分子中に２個以上のエポキシ基
を有するエポキシ化合物は、ＩＣ封止材料、成型材料、
接着剤、各種無機物の表面処理、合成樹脂安定剤、ポリ
マーアロイの相溶化剤等として用いられている。これら
のエポキシ化合物の中でも、脂環式のエポキシ化合物は
着色変化が少なく、また、汎用のグリシジル化合物と比
較して反応性に優れるという特徴を有している。Epoxy compounds, especially epoxy compounds having two or more epoxy groups in one molecule, are used as IC sealing materials, molding materials,
It is used as an adhesive, a surface treatment agent for various inorganic materials, a synthetic resin stabilizer, a compatibilizer for polymer alloys, etc. Among these epoxy compounds, alicyclic epoxy compounds are characterized by less color change and superior reactivity compared to general-purpose glycidyl compounds.
しかしながら、脂環式エポキシ化合物はその構造の特異
性ゆえに高分子量化ができず、特に、１分子中に多数の
エポキシ基を持たせることが困難であった。However, alicyclic epoxy compounds cannot be made to have a high molecular weight due to their structural specificity, and in particular, it has been difficult to have a large number of epoxy groups in one molecule.
本発明は、分子中に複数の脂環式エポキシ基を有するエ
ポキシ化合物を提供することを目的とするものであり、
脂環式エポキシ基を結合する幹骨格としてメチルオリゴ
またはポリシロキサンを用いるものである。The object of the present invention is to provide an epoxy compound having a plurality of alicyclic epoxy groups in the molecule,
Methyl oligo or polysiloxane is used as the backbone for bonding alicyclic epoxy groups.
即ち、本願発明は次の一般式（Ｉ）で表されるエポキシ
基含有シラン化合物を提供するものである。That is, the present invention provides an epoxy group-containing silane compound represented by the following general formula (I).
（Ｒ１およびＲ２は末端基を示す。Ｒ１は次の式（ＩＩ
）で表される２−（２，３−エポキシノルボルネン５−
イル）エチル基または炭素原子数４〜３０のアルキル基
を示し、複数のＲ１の少なくとも二つは２−（２，３−
エポキシノルボルネン−５−イル）エチル基を示す。ｎ
は１〜８０を示す。〕以下、本願発明の上記エポキシ基
含有シラン化合物について更に詳細に説明する。(R1 and R2 represent terminal groups. R1 is represented by the following formula (II
) 2-(2,3-epoxynorbornene 5-
yl)ethyl group or an alkyl group having 4 to 30 carbon atoms, and at least two of the plurality of R1s are 2-(2,3-
Indicates an epoxynorbornen-5-yl)ethyl group. n
indicates 1 to 80. ] Hereinafter, the above-mentioned epoxy group-containing silane compound of the present invention will be explained in more detail.
上記−最大（Ｉ）で表される化合物は、例えば、Ｉｔ−
３ｔ （ＣＨ：Ｉ） ｚ−０−Ｓｔ （ＣＨ３） ｚ−
Ｈ（テトラメチルジシロキサン） 、−（Ｓｉ （Ｈ）
（ＣＨ３） −０）−（メチルポリシロキサン）等の
分子中に２個以上のＳ ｉ −ＩＩ結合を有するシロキ
サン化合物と２．３−エポキシ−５−ビニルノルボルネ
ンあるいはこれと炭素原子数４〜３０のα−オレフィン
（例えば、ブテン、ヘキセン、オクテン、ノネン、デセ
ン、ドデセン、オクタデセン、エイコセン、トリアコン
チン等）との混合物を、好ましくは、塩化白金酸等の触
媒の存在下に反応させることによって容易に製造するこ
とができる。The compound represented by -maximum (I) above is, for example, It-
3t (CH:I) z-0-St (CH3) z-
H (tetramethyldisiloxane), -(Si (H)
A siloxane compound having two or more Si-II bonds in the molecule such as (CH3)-0)-(methylpolysiloxane) and 2,3-epoxy-5-vinylnorbornene or this with a carbon number of 4 to 30 of α-olefins (e.g., butene, hexene, octene, nonene, decene, dodecene, octadecene, eicosene, triacontin, etc.), preferably in the presence of a catalyst such as chloroplatinic acid. can be manufactured.
また、本発明の化合物は、２，３−エポキシ５−ビニル
ノルボルネンあるいはこれと炭素原子数４〜３０のα−
オレフィンとの混合物を、Ｈ−Ｓ １（ＣＨｓ） ｚ−
０−ＣｚＨｓ （ジメチルエトキシシラン） 、Ｈ−Ｓ
ｔ（ＣＨｓ） −（０−ＣｔＨｓ） ｚ （メチルジェ
トキシシラン）、１１Ｓｉ （ＣＨｓ） ｚ−ＣＩ （
ジメチルクロロシラン） 、Ｉｔ−５ｉ （Ｃ１１３）
−Ｃｈ （メチルジクロロシラン）等のＳ ｉ −ＩＩ
基およびアルコキシ基またはハロゲン原子を有する単量
体型のシロキサン化合物によってシリル化した後、これ
を三量化あるいは重合することによっても製造できる。In addition, the compound of the present invention may be 2,3-epoxy 5-vinylnorbornene or α-
The mixture with olefin is converted into H-S 1(CHs) z-
0-CzHs (dimethylethoxysilane), H-S
t(CHs) -(0-CtHs) z (methyljethoxysilane), 11Si (CHs) z-CI (
dimethylchlorosilane), It-5i (C113)
S i -II such as -Ch (methyldichlorosilane)
It can also be produced by silylation with a monomeric siloxane compound having a group and an alkoxy group or a halogen atom, followed by trimerization or polymerization.
また、原料として用いるメチルポリシロキサンにおける
末端基あるいはメチルジェトキシシランでシリル化した
後に重合させる場合の末端基は特に制限を受けず、末端
停止剤を用いない場合には原料単量体に由来するアルコ
キシ基あるいはこれが加水分解された水酸基であっても
よく、また、分子量の調節等を目的としてジメチルエト
キシシラン、トリメチルエトキシシラン等の単官能性の
シロキサン化合物を用いた場合にはメチル基等のアルキ
ル基であってもよい。In addition, the terminal groups in methylpolysiloxane used as a raw material or the terminal groups in the case of polymerization after silylation with methyljethoxysilane are not particularly limited, and when no terminal capping agent is used, the terminal groups originate from the raw material monomer. It may be an alkoxy group or a hydroxyl group obtained by hydrolyzing this, and when a monofunctional siloxane compound such as dimethylethoxysilane or trimethylethoxysilane is used for the purpose of controlling the molecular weight, an alkyl group such as a methyl group may be used. It may be a base.
従って、上記−最大（Ｉ）で表される化合物におけるＲ
１およびＲｔで表される末端基としては、例えば、メチ
ル基、メトキシ基、エトキシ基、水酸基、トリメチルシ
ロキシ基等があげられる。Therefore, R in the compound represented by maximum (I) above
Examples of the terminal group represented by 1 and Rt include a methyl group, a methoxy group, an ethoxy group, a hydroxyl group, and a trimethylsiloxy group.
かくして得られる本発明のエポキシ基含有シラン化合物
は、前述のごとく、ＩＣ封止材料、成型材料、接着剤、
炭酸カルシウム、タルク等の各種無機物の表面処理、合
成樹脂安定剤、ポリフェニレンオキサイド、ポリカーボ
ネート、ポリアミドポリエチレンテレフタレート、ポリ
ブチレンテレフタレート等の所謂エンジニアリングプラ
スチックを用いたポリマーアロイの相溶化剤等として用
いることができる。The epoxy group-containing silane compound of the present invention thus obtained can be used as an IC sealing material, a molding material, an adhesive,
It can be used for surface treatment of various inorganic substances such as calcium carbonate and talc, as a synthetic resin stabilizer, and as a compatibilizer for polymer alloys using so-called engineering plastics such as polyphenylene oxide, polycarbonate, polyamide polyethylene terephthalate, and polybutylene terephthalate.
以下、実施例によって本願発明をさらに詳細に説明する
。Hereinafter, the present invention will be explained in more detail with reference to Examples.
実施例１
テトラメチル・ビス（２−（２，３−エポキシノノルボ
ルネンー５−イル）エチルフジシロキサンテトラメチル
ジシロキサン３．４ｇ、２．３エポキシ−５−ビニルノ
ルボルネン１．２ｇ及び塩化白金酸２０■をとり、トル
エン溶媒中、９０〜１００°Ｃで８時間攪拌した。Example 1 Tetramethyl bis(2-(2,3-epoxynonorbornen-5-yl)ethylfudisiloxane 3.4 g of tetramethyldisiloxane, 1.2 g of 2.3 epoxy-5-vinylnorbornene and chloroplatinic acid 20 ml of the solution was taken and stirred in a toluene solvent at 90-100°C for 8 hours.
活性炭１ｇを加えセライトろ過した後、減圧下にトルエ
ンを留去して無色液体の生成物Ｌｏｇを得た。After adding 1 g of activated carbon and filtering through Celite, toluene was distilled off under reduced pressure to obtain a colorless liquid product Log.
生成物の分析結果は下記の通りであり、目的物であるこ
とを確認した。The analysis results of the product were as follows, and it was confirmed that it was the desired product.
オキシラン酸素： ７．７０％（計算値： ７．８８％
）屈折率（ｎ ｚｓ） ： １．４８８８赤外線分光
分析（ｃｍ−’）
１２６０ｃｍ−’： ５ｉ−ＣＨ３，１０６１０６Ｏ’
（ｂｒｏａｄ）： ５ｔ−０゜８４５ｃＩＩＩ−Ｉ：
エポキシ環
核磁気共鳴スペクトル
３、ｌｌｐｐｍ： ２１（、エポキシ環に結合した水素
原子２．４０ｐｐｍ： ２１１ 、ノルボルネン環の三
級水素原子０．０４ｐＩ）ｍ： ６Ｈ，２個のメチル基
実施例２
ポリ〔メチル・２−（２，３−エポキシノルポル平均重
合度約１５のメチルポリシロキサン３ｇ、２．３−エポ
キシ−５−ビニルノルボルネン６゜８ｇ及び塩化白金酸
３０■をとり、トルエン溶媒中、９０〜１００°Ｃで８
時間攪拌した。Oxirane oxygen: 7.70% (calculated value: 7.88%
) Refractive index (nzs): 1.4888 Infrared spectroscopy (cm-') 1260cm-': 5i-CH3,106106O'
(broad): 5t-0°845cIII-I:
Epoxy ring nuclear magnetic resonance spectrum 3, llppm: 21 (, hydrogen atom bonded to epoxy ring 2.40ppm: 211, tertiary hydrogen atom of norbornene ring 0.04pI) m: 6H, 2 methyl groups Example 2 Poly [Methyl 2-(2,3-epoxynorpol) 3 g of methylpolysiloxane with an average degree of polymerization of about 15, 6.8 g of 2,3-epoxy-5-vinylnorbornene and 30 μl of chloroplatinic acid were taken in a toluene solvent, 8 at 90-100°C
Stir for hours.
活性炭１ｇを加えセライトろ過した後、減圧下にトルエ
ンを留去して灰色粘稠液体の生成物８ｇを得た。After adding 1 g of activated carbon and filtering through Celite, toluene was distilled off under reduced pressure to obtain 8 g of a gray viscous liquid product.
生成物の分析結果は下記の通りであり、目的物であるこ
とを確認した。The analysis results of the product were as follows, and it was confirmed that it was the desired product.
オキシラン酸素７８．０１％（計算値：８．１６％）屈
折率（ｎ ｚｓ） ： １．５０４９赤外線分光分析
（ｃｍ−’）
１２６０ｃ＋ｓ−’： ５ｉ−Ｃ１１，，１０２０およ
び１０９１０９Ｏ’： ５ｉ−０，８５０ｃｍ−’：
エポキシ環
核磁気共鳴スペクトル
３．１０ｐｌ）ｍ： ２Ｈ、エポキシ環に結合した水素
原子２．４２ｐｐｍ： ２Ｈ、ノルボルネン環の三級水
素原子０、Ｏ７ｐｐｍ： ３Ｈ、メチル基
実施例３
ポリ〔メチル・２−（２，３−エポキシノルボルネン−
５−イル）エチルシロキサン／メチル・オクチルシロキ
サン の八
核磁気共鳴スペクトル
３．１０ｐｐｍ： ２Ｈ、エポキシ環に結合した水素原
子２．４２ｐｐｍ： ２１１ 、ノルボルネン環の三級
水素原子０、Ｏ７ｐｐｍ： ３Ｈ、メチル基
平均重合度約１５のメチルポリシロキサン６ｇ、２．３
−エポキシ−５−ビニルノルボルネン６゜８ｇ、１−オ
クテン６．３ｇ及び塩化白金酸４０■をとり、トルエン
溶媒中９０〜１００ ’Ｃで８時間攪拌した。Oxirane Oxygen 78.01% (calculated value: 8.16%) Refractive index (nzs): 1.5049 Infrared spectroscopy (cm-') 1260c+s-': 5i-C11,,1020 and 109109O': 5i-0 ,850cm-':
Epoxy ring nuclear magnetic resonance spectrum 3.10 pl) m: 2H, hydrogen atom bonded to epoxy ring 2.42 ppm: 2H, tertiary hydrogen atom of norbornene ring 0, O7 ppm: 3H, methyl group Example 3 Poly[methyl 2 -(2,3-epoxynorbornene-
Octanuclear magnetic resonance spectrum of 5-yl)ethylsiloxane/methyl octylsiloxane 3.10 ppm: 2H, hydrogen atom bonded to epoxy ring 2.42 ppm: 211, tertiary hydrogen atom of norbornene ring 0, O7 ppm: 3H, methyl 6 g of methylpolysiloxane with a group average degree of polymerization of about 15, 2.3
-Epoxy-5-vinylnorbornene (6.8 g), 1-octene (6.3 g) and chloroplatinic acid (40 g) were taken and stirred in a toluene solvent at 90-100'C for 8 hours.
活性炭１ｇを加えセライトろ過した後、減圧下にトルエ
ンを留去して無色液体の生成物１７ｇを得た。After adding 1 g of activated carbon and filtering through Celite, toluene was distilled off under reduced pressure to obtain 17 g of a colorless liquid product.
生成物の分析結果は下記の通りであり、目的物であるこ
とを確認した。The analysis results of the product were as follows, and it was confirmed that it was the desired product.
オキシラン酸素： ４．３０％（計算値： ４．３５％
）屈折率（ｎ ｚｓ） ： １．４７６５赤外線分光
分析（ｃｍ−’）
１２５５ＣＤ＋−’ ： ５ｔ−ＣＨ：＋、１０００〜
１１００ｃｍ−’： ５ｉ−０，８４０ｃｍ−’： エ
ポキシ環Oxirane oxygen: 4.30% (calculated value: 4.35%
) Refractive index (nzs): 1.4765 Infrared spectroscopic analysis (cm-') 1255CD+-': 5t-CH:+, 1000~
1100cm-': 5i-0,840cm-': Epoxy ring
Claims (1)
合物。 ▲数式、化学式、表等があります▼（ I ） 〔Ｒ＿１およびＲ＿２は末端基を示す。Ｒ＿３は次の式
（II）で表される２−（２，３−エポキシノルボルネン
−５−イル）エチル基または炭素原子数４〜３０のアル
キル基を示し、複数のＲ＿３の少なくとも二つは２−（
２，３−エポキシノルボルネン−５−イル）エチル基を
示す。ｎは１〜８０を示す。〕 ▲数式、化学式、表等があります▼（II）[Claims] An epoxy group-containing silane compound represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [R_1 and R_2 indicate terminal groups. R_3 represents a 2-(2,3-epoxynorbornen-5-yl)ethyl group or an alkyl group having 4 to 30 carbon atoms represented by the following formula (II), and at least two of the plurality of R_3 are 2 −(
2,3-epoxynorbornen-5-yl)ethyl group. n represents 1 to 80. ] ▲ Contains mathematical formulas, chemical formulas, tables, etc. ▼ (II)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2809689A JPH02207087A (en) | 1989-02-07 | 1989-02-07 | Epoxy-group-containing silane compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2809689A JPH02207087A (en) | 1989-02-07 | 1989-02-07 | Epoxy-group-containing silane compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02207087A true JPH02207087A (en) | 1990-08-16 |
Family
ID=12239262
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2809689A Pending JPH02207087A (en) | 1989-02-07 | 1989-02-07 | Epoxy-group-containing silane compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02207087A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015041325A1 (en) * | 2013-09-20 | 2015-03-26 | 信越化学工業株式会社 | Silicone-modified epoxy resin and composition and cured article thereof |
| US20170073457A1 (en) * | 2014-02-19 | 2017-03-16 | Shin-Etsu Chemical Co., Ltd. | Silicone-modified epoxy resin, composition containing said epoxy resin, and cured product thereof |
-
1989
- 1989-02-07 JP JP2809689A patent/JPH02207087A/en active Pending
Cited By (9)
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|---|---|---|---|---|
| WO2015041325A1 (en) * | 2013-09-20 | 2015-03-26 | 信越化学工業株式会社 | Silicone-modified epoxy resin and composition and cured article thereof |
| CN105873976A (en) * | 2013-09-20 | 2016-08-17 | 信越化学工业株式会社 | Silicone-modified epoxy resin and composition and cured article thereof |
| US20160237202A1 (en) * | 2013-09-20 | 2016-08-18 | Shin-Etsu Chemical Co., Ltd. | Silicone-modified epoxy resin and composition and cured article thereof |
| JPWO2015041325A1 (en) * | 2013-09-20 | 2017-03-02 | 信越化学工業株式会社 | Silicone-modified epoxy resin and composition and cured product thereof |
| US9777107B2 (en) | 2013-09-20 | 2017-10-03 | Shin-Etsu Chemical Co., Ltd. | Silicone-modified epoxy resin and composition and cured article thereof |
| TWI629307B (en) * | 2013-09-20 | 2018-07-11 | 日商信越化學工業股份有限公司 | Polyoxymethylene modified epoxy resin and its composition and hardened material |
| US20170073457A1 (en) * | 2014-02-19 | 2017-03-16 | Shin-Etsu Chemical Co., Ltd. | Silicone-modified epoxy resin, composition containing said epoxy resin, and cured product thereof |
| JPWO2015125803A1 (en) * | 2014-02-19 | 2017-03-30 | 信越化学工業株式会社 | Silicone-modified epoxy resin, composition containing the epoxy resin, and cured product thereof |
| US9944760B2 (en) * | 2014-02-19 | 2018-04-17 | Shin-Etsu Chemical Co., Ltd. | Silicone-modified epoxy resin, composition containing said epoxy resin, and cured product thereof |
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