JPH054995A - Organosilicon compound and production thereof - Google Patents

Organosilicon compound and production thereof

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Publication number
JPH054995A
JPH054995A JP3017164A JP1716491A JPH054995A JP H054995 A JPH054995 A JP H054995A JP 3017164 A JP3017164 A JP 3017164A JP 1716491 A JP1716491 A JP 1716491A JP H054995 A JPH054995 A JP H054995A
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Japan
Prior art keywords
chemical
formula
group
compound
sich
Prior art date
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Japanese (ja)
Inventor
Masaaki Yamatani
正明 山谷
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Shin Etsu Chemical Co Ltd
Original Assignee
Shin Etsu Chemical Co Ltd
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Priority to JP3017164A priority Critical patent/JPH054995A/en
Publication of JPH054995A publication Critical patent/JPH054995A/en
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

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  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

PURPOSE:To provide the title new compound useful for synthesizing multifunctional silane coupling agents, cross-linking agents for silicone resins, etc. CONSTITUTION:The objective organosilicon compound of formula I [A is H or of formula II (R<1> is >=4C divalent organic group; X is hydrolyzable group; n is 1-3); however, at least one of four As being of formula II], for example, a compound of formula III. The present compound can be obtained by reaction in the presence of a transition metal compound (pref. platinum or palladium) between (A) 1,3,5,7-tetramethlycyclotetrasiloxane of formula IV and (B) a unsaturated double bond-terminated organosilane of formula V (R<2> is >=2C divalent organic group; R<3> is H or methyl). The reaction is preferably made at room temperature to 150 deg.C. The compound of the formula V is e.g. 6- trimethoxysilyl-1-hexane.

Description

【発明の詳細な説明】Detailed Description of the Invention

【０００１】[0001]

【産業上の利用分野】本発明は文献未載の新規な有機け
い素化合物、特には多官能性シランカップリング剤や異
官能性シランカップリング剤、さらにはシリコーン樹脂
用架橋剤の合成に有用とされる新規な有機けい素化合物
に関するものである。FIELD OF THE INVENTION The present invention is useful for the synthesis of novel organosilicon compounds which have not been published in the literature, especially polyfunctional silane coupling agents and heterofunctional silane coupling agents, and further crosslinking agents for silicone resins. The present invention relates to a novel organosilicon compound.

【０００２】[0002]

【発明の構成】本発明は文献未載の新規な有機けい素化
合物およびその製造方法に関するものであり、このもの
は一般式DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel organic silicon compound which has not been published in the literature, and a method for producing the same.

【０００３】[0003]

【化５】 [Chemical 5]

【０００４】で示され、Ａは水素原子または式-R1-Si(C
H3)3-nXnで示される基で、R1は -CH2-CH2CH2CH2-, -CH2
CH(CH3)CH2-, -CH2CH2CH2CH2CH2CH2-, -CH2CH2CH2CH2CH
2CH2CH2CH2CH2CH2-,A is a hydrogen atom or the formula --R 1 --Si (C
H 3 ) 3-n X n , R 1 is -CH 2 -CH 2 CH 2 CH 2- , -CH 2
CH (CH 3 ) CH 2- , -CH 2 CH 2 CH 2 CH 2 CH 2 CH 2- , -CH 2 CH 2 CH 2 CH 2 CH
2 CH 2 CH 2 CH 2 CH 2 CH 2- ,

【０００５】[0005]

【化６】 [Chemical 6]

【０００６】[0006]

【化７】 [Chemical 7]

【０００７】[0007]

【化８】 [Chemical 8]

【０００８】などで示される炭素数４以上の２価の有機
基、Ｘは-OCH3, -OCH2CH3, -OCH2CH2CH2CH3, -O-CCH3=C
H2、 -O-COCH3、 -O-N=CCH3-CH2CH3、 -Cl、 -NH2 など、好
ましくは保存時、使用時の安定性から-OCH3, -OCH2CH3
などのアルコキシ基とされる加水分解性基、ｎは１，２
または３であり、この４個のＡのうち少なくとも１個は
上記の-R1-Si(CH3)3-nXn基であるものである。A divalent organic group having 4 or more carbon atoms represented by, for example, X is --OCH 3 , --OCH 2 CH 3 , --OCH 2 CH 2 CH 2 CH 3 , --O--CCH 3 = C
H 2, -O-COCH 3 , -ON = CCH 3 -CH 2 CH 3 , -Cl, -NH 2, etc., preferably -OCH 3 , -OCH 2 CH 3 from the stability during storage and use.
A hydrolyzable group such as an alkoxy group, n is 1, 2
Or 3, and at least one of the four A is the above-mentioned —R 1 —Si (CH 3 ) 3-n X n group.

【０００９】この一般式(1) で示される有機けい素化合
物としてはAs the organic silicon compound represented by the general formula (1),

【００１０】[0010]

【化９】 [Chemical 9]

【００１１】[0011]

【化１０】 [Chemical 10]

【００１２】[0012]

【化１１】 [Chemical 11]

【００１３】[0013]

【化１２】 [Chemical 12]

【００１４】[0014]

【化１３】 [Chemical 13]

【００１５】[0015]

【化１４】 [Chemical 14]

【００１６】[0016]

【化１５】 [Chemical 15]

【００１７】[0017]

【化１６】 [Chemical 16]

【００１８】[0018]

【化１７】 [Chemical 17]

【００１９】[0019]

【化１８】 [Chemical 18]

【００２０】[0020]

【化１９】 [Chemical 19]

【００２１】[0021]

【化２０】 [Chemical 20]

【００２２】[0022]

【化２１】 [Chemical 21]

【００２３】[0023]

【化２２】 [Chemical formula 22]

【００２４】[0024]

【化２３】 [Chemical formula 23]

【００２５】[0025]

【化２４】 [Chemical formula 24]

【００２６】[0026]

【化２５】 [Chemical 25]

【００２７】[0027]

【化２６】 [Chemical formula 26]

【００２８】[0028]

【化２７】 [Chemical 27]

【００２９】[0029]

【化２８】 [Chemical 28]

【００３０】[0030]

【化２９】 [Chemical 29]

【００３１】[0031]

【化３０】 [Chemical 30]

【００３２】[0032]

【化３１】 [Chemical 31]

【００３３】[0033]

【化３２】 [Chemical 32]

【００３４】[0034]

【化３３】 [Chemical 33]

【００３５】[0035]

【化３４】 [Chemical 34]

【００３６】[0036]

【化３５】 [Chemical 35]

【００３７】[0037]

【化３６】 [Chemical 36]

【００３８】などが例示されるが、これはこの具体例に
限定されるものではない。Although the above is exemplified, this is not limited to this specific example.

【００３９】また、本発明の有機けい素化合物は式The organic silicon compound of the present invention has the formula

【００４０】[0040]

【化３７】 [Chemical 37]

【００４１】で示される1,3,5,7 −テトラメチルシクロ
テトラシロキサンと一般式1,3,5,7-tetramethylcyclotetrasiloxane represented by

【００４２】[0042]

【化３８】 [Chemical 38]

【００４３】で示され、R2が炭素数２以上の２価の有機
基、R3が水素原子またはメチル基、Ｘが加水分解性基、
ｎが１，２または３であるオルガノシランとを遷移金属
化合物の存在下に反応させることによって得ることがで
きる。R 2 is a divalent organic group having 2 or more carbon atoms, R 3 is a hydrogen atom or a methyl group, X is a hydrolyzable group,
It can be obtained by reacting an organosilane in which n is 1, 2 or 3 in the presence of a transition metal compound.

【００４４】なお、上記におけるR2は前記したR1の例示
から-CH2-CH2- を除いたものであり、加水分解性基Ｘは
前記と同じものであるが、ここに使用される前記した式
(2)で示されるオルガノシランとしては下記のものIn the above, R 2 is the above-mentioned R 1 excluding --CH 2 --CH 2- , and the hydrolyzable group X is the same as above, but it is used here. The above formula
The organosilanes represented by (2) are as follows:

【００４５】CH2=CH-(CH2)4Si(OCH2CH3)3 CH2=CH-(CH2)4SiCH3(OCH2CH3)2 CH2=CH-(CH2)4Si(OCH2CH2CH2CH3)3 CH2=CH-(CH2)4Si(O-COCH3)3 CH2=CH-(CH2)4SiCH3(O-COCH3)2 CH2=CH-(CH2)4Si(O-CCH3=CH2)3 CH2=CH-(CH2)4SiCH3(O-CCH3=CH2)2 CH2=CH-(CH2)4Si(O-N=CCH3-CH2CH3)3 CH2=CH-(CH2)4SiCH3(O-N=CCH3-CH2CH3)2 CH2=CH-(CH2)4Si(NH2)3 CH2=CH-(CH2)4SiCH3(NH2)2 CH2=CH-(CH2)4SiCl3 CH2=CH-(CH2)4SiCH3Cl2 CH2=CH-(CH2)2Si(OCH3)3 CH2=CH-(CH2)2SiCH3(OCH3)2 CH2=CH-(CH2)2Si(OCH2CH3)3 CH2=CH-(CH2)2SiCH3(O-CH2CH3)2 CH2=CH-(CH2)2Si(OCCH3=CH2)3 CH2=CH-(CH2)2SiCH3(OCCH3CH2)2 CH2=CH-(CH2)2SiCl3 CH2=CH-(CH2)2SiCH3Cl2 CH2=CH-(CH2)2Si(NH2)3 CH2=CH-(CH2)2SiCH3(NH2)2 CH2=CH-(CH2)8Si(OCH3)3 CH2=CH-(CH2)8SiCH3(OCH3)2 CH2=CH-(CH2)8Si(OCH2CH3)3 CH2=CH-(CH2)8SiCH3(OCH2CH3)2 CH2=CH-(CH2)8Si(O-CCH3=CH2)3 CH2=CH-(CH2)8SiCH3(O-CCH3=CH2)2 CH2=CH-(CH2)8SiCl3 CH2=CH-(CH2)8SiCH3Cl2 CH2=CH-(CH2)8Si(NH2)3 CH2=CH-(CH2)8SiCH3(NH2)2 CH2=CH-(CH2)12Si(OCH3)3 CH2=CH-(CH2)12SiCH3(OCH3)2 CH2=CH-(CH2)12Si(O-CCH3=CH2)3 CH2=CH-(CH2)12SiCH3(O-CCH3=CH2)2 CH2=CH-(CH2)12SiCl3 CH2=CH-(CH2)12SiCH3Cl2 CH2=CH-(CH2)12Si(NH2)3 CH2=CH-(CH2)12SiCH3(NH2)2 CH 2 = CH- (CH 2 ) 4 Si (OCH 2 CH 3 ) 3 CH 2 = CH- (CH 2 ) 4 SiCH 3 (OCH 2 CH 3 ) 2 CH 2 = CH- (CH 2 ) 4 Si (OCH 2 CH 2 CH 2 CH 3 ) 3 CH 2 = CH- (CH 2 ) 4 Si (O-COCH 3 ) 3 CH 2 = CH- (CH 2 ) 4 SiCH 3 (O-COCH 3 ) 2 CH 2 = CH- (CH 2 ) 4 Si (O-CCH 3 = CH 2 ) 3 CH 2 = CH- (CH 2 ) 4 SiCH 3 (O-CCH 3 = CH 2 ) 2 CH 2 = CH- (CH 2 ) 4 Si (ON = CCH 3 -CH 2 CH 3 ) 3 CH 2 = CH- (CH 2 ) 4 SiCH 3 (ON = CCH 3 -CH 2 CH 3 ) 2 CH 2 = CH- (CH 2 ) 4 Si (NH 2 ) 3 CH 2 = CH- (CH 2 ) 4 SiCH 3 (NH 2 ) 2 CH 2 = CH- (CH 2 ) 4 SiCl 3 CH 2 = CH- (CH 2 ) 4 SiCH 3 Cl 2 CH 2 = CH- (CH 2) 2 Si (OCH 3) 3 CH 2 = CH- (CH 2) 2 SiCH 3 (OCH 3) 2 CH 2 = CH- (CH 2) 2 Si (OCH 2 CH 3) 3 CH 2 = CH- (CH 2 ) 2 SiCH 3 (O-CH 2 CH 3 ) 2 CH 2 = CH- (CH 2 ) 2 Si (OCCH 3 = CH 2 ) 3 CH 2 = CH- (CH 2 ) 2 SiCH 3 (OCCH 3 CH 2 ) 2 CH 2 = CH- (CH 2 ) 2 SiCl 3 CH 2 = CH- (CH 2 ) 2 SiCH 3 Cl 2 CH 2 = CH- (CH 2 ) 2 Si (NH 2 ) 3 CH 2 = CH- (CH 2 ) 2 SiCH 3 (NH 2 ) 2 CH 2 = CH- (CH 2 ) 8 Si (OCH 3 ) 3 CH 2 = CH- (CH 2 ) 8 SiCH 3 (OCH 3 ) 2 CH 2 = CH- (CH 2 ) 8 Si (OCH 2 CH 3 ) 3 CH 2 = CH- (CH 2 ) 8 SiCH 3 (OCH 2 CH 3 ) 2 CH 2 = CH- (CH 2 ) 8 Si (O-CCH 3 = CH 2 ) 3 CH 2 = CH- (CH 2 ) 8 SiCH 3 (O-CCH 3 = CH 2 ) 2 CH 2 = CH- (CH 2 ) 8 SiCl 3 CH 2 = CH- (CH 2 ) 8 SiCH 3 Cl 2 CH 2 = CH- (CH 2 ) 8 Si (NH 2 ) 3 CH 2 = CH - (CH 2) 8 SiCH 3 (NH 2) 2 CH 2 = CH- (CH 2) 12 Si (OCH 3) 3 CH 2 = CH- (CH 2) 12 SiCH 3 (OCH 3) 2 CH 2 = CH -(CH 2 ) 12 Si (O-CCH 3 = CH 2 ) 3 CH 2 = CH- (CH 2 ) 12 SiCH 3 (O-CCH 3 = CH 2 ) 2 CH 2 = CH- (CH 2 ) 12 SiCl 3 CH 2 = CH- (CH 2 ) 12 SiCH 3 Cl 2 CH 2 = CH- (CH 2 ) 12 Si (NH 2 ) 3 CH 2 = CH- (CH 2 ) 12 SiCH 3 (NH 2 ) 2

【００４６】[0046]

【化３９】 [Chemical Formula 39]

【００４７】[0047]

【化４０】 [Chemical 40]

【００４８】[0048]

【化４１】 [Chemical 41]

【００４９】[0049]

【化４２】 [Chemical 42]

【００５０】[0050]

【化４３】 [Chemical 43]

【００５１】[0051]

【化４４】 [Chemical 44]

【００５２】が例示されるし、ここに使用される遷移金
属化合物としては白金、ロジウム、ルテニウム、パラジ
ウム系の化合物が特に好ましいものとされる。Examples of the transition metal compound include platinum, rhodium, ruthenium and palladium compounds.

【００５３】この反応はヒドロシリル化反応であり、使
用される遷移金属化合物は触媒として作用するものであ
るが、この反応条件は室温から150 ℃位の範囲とすれば
よく、これはトルエン、キシレン、ＴＨＦ、ジオキサン
などの溶剤存在下でしてもよい。This reaction is a hydrosilylation reaction, and the transition metal compound used acts as a catalyst, but the reaction conditions may be room temperature to 150 ° C., such as toluene, xylene, It may be performed in the presence of a solvent such as THF or dioxane.

【００５４】また、この反応は本発明の有機けい素化合
物が≡Si-H基を含有するものであることから、部分ヒド
ロシリル化反応させる必要があるので、過剰の1,3,5,7
−テトラメチルシクロテトラシロキサンとヒドロシリル
化触媒との混合物中に末端不飽和二重結合含有オルガノ
シランを滴下して反応させればよいが、この際のテトラ
メチルシクロテトラシロキサン／末端不飽和二重結合含
有オルガノシランのモル比はこれが0.3 未満であると有
機官能基を導入するための手掛りとなる≡Si-H基がほと
んど残存しなくなるし、10.0より多くすると目的物のポ
ット収率が低くなり過ぎてコスト的に不利となるので、
0.3 〜10.0の範囲とすればよいが、この好ましい範囲は
0.5 〜5.0 とされる。Further, since this reaction requires the partial hydrosilylation reaction because the organosilicon compound of the present invention contains an ≡Si--H group, an excess of 1,3,5,7 is required.
-A terminal unsaturated double bond-containing organosilane may be added dropwise to a mixture of tetramethylcyclotetrasiloxane and a hydrosilylation catalyst to cause a reaction. In this case, tetramethylcyclotetrasiloxane / terminal unsaturated double bond When the molar ratio of the contained organosilane is less than 0.3, the ≡Si-H group, which is a clue for introducing the organic functional group, hardly remains, and when it is more than 10.0, the pot yield of the target product becomes too low. Will be disadvantageous in terms of cost,
The range may be 0.3 to 10.0, but the preferred range is
It is set to 0.5 to 5.0.

【００５５】本発明の有機けい素化合物はこのヒドロシ
リル化反応終了後、蒸溜精製して使用すればよいが、こ
れは低沸点分を溜去したのちの混合物をそのまま使用し
てもよく、さらには必要に応じ窒素原子または硫黄原子
を含有する化合物を投入してヒドロシリル化触媒を失活
させてその安定性を向上させてもよい。The organosilicon compound of the present invention may be used by distillation purification after the completion of the hydrosilylation reaction, and the mixture obtained by distilling off the low boiling point component may be used as it is. If necessary, a compound containing a nitrogen atom or a sulfur atom may be added to deactivate the hydrosilylation catalyst to improve its stability.

【００５６】このようにして作られた本発明の有機けい
素化合物は１分子中に≡Si-H基と少なくとも１個の-R1-
Si(CH3)3-n-Xn 基を有しているので、これは多官能性シ
ランカップリング剤や異官能性シランカップリング剤の
合成原料として、およびシリコーン樹脂架橋剤などとし
て有用とされる。The organosilicon compound of the present invention thus produced has ≡Si—H group and at least one —R 1 — in one molecule.
Since a Si (CH 3) 3-n -X n groups, which as a starting material for the synthesis of multi-functional silane coupling agents and cross-functional silane coupling agent, and useful as a silicone resin crosslinking agent To be done.

【００５７】すなわち、本発明の有機けい素化合物とア
リルグリシジルエ−テル、アリルメタクリレ−ト、３，
４−エポキシ−１−ビニルシクロヘキサン、アリルクロ
ライドなどのビニル基含有化合物の１種類とを、遷移金
属化合物の存在下でヒドロシリル化反応させると、有機
官能基を複数個有する多官能性シランカップリング剤と
することができるし、このビニル基含有化合物を２種類
以上とすれば異種の有機官能基を１分子中に合わせもつ
異官能性シランカップリング剤を合成することができ
る。なお、このシリコ−ン樹脂の架橋剤としてはこのま
ま使用することができるが、これは付加／縮合兼用タイ
プとすることもできる。That is, the organosilicon compound of the present invention and allyl glycidyl ether, allyl methacrylate, 3,
When a hydrosilylation reaction is carried out with one type of a vinyl group-containing compound such as 4-epoxy-1-vinylcyclohexane and allyl chloride in the presence of a transition metal compound, a polyfunctional silane coupling agent having a plurality of organic functional groups. If two or more kinds of vinyl group-containing compounds are used, a heterofunctional silane coupling agent having different organic functional groups in one molecule can be synthesized. The silicone resin can be used as it is as a cross-linking agent, but it may be an addition / condensation type.

【００５８】[0058]

【実施例】つぎに本発明の実施例をあげる。 実施例１ 撹拌機、ジムロート冷却管、温度計、滴下漏斗を備え付
けた１Ｌの反応器に、窒素雰囲気下で1,3,5,7 −テトラ
メチルシクロテトラシロキサン（以下化合物−Ａと略記
する）を432 ｇ（1.8 モル）仕込み、60℃まで昇温し、
ここに塩化白金酸0.5 重量％含有エタノール溶液を1.2
ｇ添加したのち、直ちに式 [(CH3)3O]3Si-CH2CH2CH2CH2-CH=CH2 で示される６−トリメトキシシリル−１−ヘキセン（化
合物−１）123.6ｇ（0.6 モル）を60〜65℃の温度を維
持するようにゆっくり滴下し、滴下終了後65〜70℃で１
時間加熱撹拌したのち蒸溜したところ、沸点が161 〜16
3 ℃／３ Torr で無色透明な液体182.0 ｇ（収率46.7
％）が得られた。EXAMPLES Next, examples of the present invention will be given. Example 1 A 1 L reactor equipped with a stirrer, a Dimroth condenser, a thermometer, and a dropping funnel was charged with 1,3,5,7-tetramethylcyclotetrasiloxane (hereinafter abbreviated as compound-A) under a nitrogen atmosphere. 432 g (1.8 mol) was charged and the temperature was raised to 60 ° C.
Add 1.2% ethanol solution containing 0.5% by weight of chloroplatinic acid.
After g added immediately formula [(CH 3) 3 O] 3 Si-CH 2 CH 2 CH 2 CH 2 -CH = represented by CH 2 6- trimethoxysilyl-1-hexene (Compound -1) 123.6 g (0.6 mol) is slowly added dropwise so as to maintain the temperature of 60 to 65 ° C.
When heated and stirred for hours, it was distilled and the boiling point was 161-116.
182.0 g (46.7% yield) of a colorless transparent liquid at 3 ° C / 3 Torr.
%)was gotten.

【００５９】このものはガスクロマトグラフ分析により
純度が96.3％であり、これは粘度5.35cS、比重1.026 、
屈折率1.4198という物性を示した。ついで、このものに
ついて赤外吸収スペクトル分析、核磁気共鳴スペクトル
分析、マススペクトル分析および元素分析を行なったと
ころ、下記のとおりの結果が得られ、このＩＲ、ＮＭＲ
については図１、図２に示したとおりの結果が得られた
ので、これは式This product had a purity of 96.3% by gas chromatographic analysis and had a viscosity of 5.35 cS, a specific gravity of 1.026,
It had a physical property of refractive index 1.4198. Then, this product was subjected to infrared absorption spectrum analysis, nuclear magnetic resonance spectrum analysis, mass spectrum analysis and elemental analysis, and the following results were obtained.
For the above, the results as shown in FIGS. 1 and 2 were obtained.

【００６０】[0060]

【化４５】 [Chemical formula 45]

【００６１】で示されるものであることが確認された。It was confirmed to be the one shown by.

【００６２】＜分析結果＞ a) 元素分析 b) 1H-NMRスペクトル分析 化学シフト（δ） 4.6 〜4.8ppm(broad s, 3H):≡Si-H， 3.46ppm(s, 9H) :-Si(OCH3 )3, 1.1 〜1.6ppm(m, 8H): (CH3O)3Si-CH2CH2 CH 2CH2 CH 2CH2-Si ≡， 0.3 〜0.8ppm(m, 4H): (CH3O)Si-CH2 CH2CH2CH2CH2CH 2-Si≡， 0.16ppm(broad s, 9H):<Analysis result> a) Elemental analysis b) 1 H-NMR spectrum analysis chemical shift (δ) 4.6 to 4.8 ppm (broad s, 3H): ≡Si- H , 3.46ppm (s, 9H): -Si (OC H 3 ) 3 , 1.1 to 1.6ppm (m, 8H): (CH 3 O) 3 Si-CH 2 C H 2 C H 2 C H 2 C H 2 CH 2 -Si ≡, 0.3 to 0.8 ppm (m, 4H): (CH 3 O) Si -C H 2 CH 2 CH 2 CH 2 CH 2 C H 2 -Si≡, 0.16ppm (broad s, 9H):

【００６３】[0063]

【化４６】 [Chemical formula 46]

【００６４】0.08ppm(s, 3H) :0.08 ppm (s, 3H):

【００６５】[0065]

【化４７】 [Chemical 47]

【００６６】c) ＩＲスペクトル分析C) IR spectrum analysis

【００６７】[0067]

【化４８】 [Chemical 48]

【００６８】実施例２ 化合物−Ａ 720ｇ（3.0 モル）と式(CH3O)3Si-CH2CH2CH
2CH2CH2CH2CH2CH2-CH=CH2 で示される10−トリメトキシ
シリル−１−デセン（化合物−２）260 ｇとを用いて実
施例１と同様に合成反応を行なったところ、沸点が185
〜188 ℃／３Torrで無色透明の液体233.5 ｇが得られた
が、このものはガスクロマトグラフ分析により純度が9
7.6％であり、これは粘度9.72cS、比重1.003 、屈折率
1.4268という物性を示した。Example 2 720 g (3.0 mol) of compound-A and the formula (CH 3 O) 3 Si—CH 2 CH 2 CH
A synthetic reaction was carried out in the same manner as in Example 1 using 260 g of 10-trimethoxysilyl-1-decene (compound-2) represented by 2 CH 2 CH 2 CH 2 CH 2 CH 2 -CH = CH 2 . However, the boiling point is 185
233.5 g of a colorless transparent liquid was obtained at ~ 188 ° C / 3 Torr, which had a purity of 9 by gas chromatography.
7.6%, which has a viscosity of 9.72 cS, a specific gravity of 1.003 and a refractive index.
It exhibited a physical property of 1.4268.

【００６９】ついで、このものについて赤外吸収スペク
トル分析、核磁気共鳴スペクトル分析、マススペクトル
分析および元素分析を行なったところ、下記のとおりの
結果が得られたので、これは式Then, when this product was subjected to infrared absorption spectrum analysis, nuclear magnetic resonance spectrum analysis, mass spectrum analysis and elemental analysis, the following results were obtained.

【００７０】[0070]

【化４９】 [Chemical 49]

【００７１】で示されるものであることが確認された。It was confirmed that the product was represented by

【００７２】＜分析結果＞ a) 元素分析 ｂ） １Ｈ−ＮＭＲスペクトル分析 化学シフト（δ） 4.6 〜4.8ppm(broad s, 3H):≡Si-H， 3.45ppm(s, 9H) : -Si(OCH 3)3, 1.1 〜1.6ppm(m,16H): (CH3O)3Si-CH2(CH2 )CH2-Si ≡， 0.3 〜0.8ppm(m, 4H): (CH3O)3Si-CH2 (CH2 )8CH2-Si≡， 0.15ppm(broad s, 9H):<Analysis Results> a) Elemental analysis b) 1 H-NMR spectroscopy chemical shifts (δ) 4.6 ~4.8ppm (broad s , 3H): ≡Si- H, 3.45ppm (s, 9H): -Si (OC H 3) 3, 1.1 ~1.6ppm (m, 16H): (CH 3 O) 3 Si-CH 2 (C H 2 ) CH 2 -Si ≡, 0.3 to 0.8 ppm (m, 4H): (CH 3 O) 3 Si-C H 2 (C H 2 ) 8 CH 2 -Si≡, 0.15 ppm (broad s, 9H):

【００７３】[0073]

【化５０】 [Chemical 50]

【００７４】0.08ppm(s, 3H) :0.08 ppm (s, 3H):

【００７５】[0075]

【化５１】 [Chemical 51]

【００７６】c) ＩＲスペクトル分析C) IR spectrum analysis

【００７７】[0077]

【化５２】 [Chemical 52]

【００７８】実施例３ 化合物−Ａ840g(3.5モル) と式(CH3O)2-Si(CH3)CH2CH2CH2
CH2-CH=CH2で示される６−ジメトキシメチルシリル−１
−ヘキセン（化合物−３） 133g (0.7g モル) とを用いて
実施例１２と同様に合成反応を行ない、合成終了後低溜
去したところ、式Example 3 840 g (3.5 mol) of Compound-A and the formula (CH 3 O) 2 —Si (CH 3 ) CH 2 CH 2 CH 2
6-dimethoxymethylsilyl-1 represented by CH 2 -CH = CH 2
-Hexene (Compound-3) 133 g (0.7 g mol) was used to carry out a synthetic reaction in the same manner as in Example 12, and after the completion of the synthesis, low distillation was carried out.

【００７９】[0079]

【化５３】 [Chemical 53]

【００８０】[0080]

【化５４】 [Chemical 54]

【００８１】[0081]

【化５５】 [Chemical 55]

【００８２】の３種の有機けい素化合物の混合物234.1g
が得られ、このものの≡Si-H含有量をアルカリ水により
発生する水素ガスを定量することによってしらべたとこ
ろ0.0057モル／g であった。234.1 g of a mixture of the three organosilicon compounds of
The content of ≡Si—H was 0.0057 mol / g as determined by quantifying hydrogen gas generated by alkaline water.

【００８３】ついで、この混合物を蒸留したところ、沸
点145 〜142 ℃／３Torrで無色透明の液体165.3g（収率
54.9％）が得られ、このものはガスクロマトグラフ分析
で純度97.5％であることが確認されてあが、これは粘度
5.23cS、比重1.001、 屈折率1.4420という物性を示し
た。Next, this mixture was distilled, and 165.3 g (yield) of a colorless transparent liquid having a boiling point of 145 to 142 ° C./3 Torr was obtained.
54.9%) was obtained, which was confirmed by gas chromatography to have a purity of 97.5%.
The physical properties were 5.23 cS, specific gravity 1.001 and refractive index 1.4420.

【００８４】つぎに、このものについて赤外線吸収スペ
クトル分析、核磁気共鳴スペクトル分析および元素分析
を行なったところ、下記のとおりの結果が得られたの
で、これは式Next, when this product was subjected to infrared absorption spectrum analysis, nuclear magnetic resonance spectrum analysis and elemental analysis, the following results were obtained.

【００８５】[0085]

【化５６】 [Chemical 56]

【００８６】で示されるものであることが確認された。It was confirmed to be the one shown by.

【００８７】＜分析結果＞ a) 元素分析 ｂ） １Ｈ−ＮＭＲスペクトル分析 化学シフト（δ） 4.65〜4.85ppm(broad s, 3H): ≡Si-H， 3.42ppm(s, 6H) : -SiCH3-(OCH 3)2, 1.1 〜1.6ppm(m, 8H): (CH3O)2SiCH3-CH2CH2 CH 2CH2 CH 2CH2-Si ≡， 0.35〜0.85ppm(m, 4H): (CH3O)2SiCH3-CH2CH2CH2CH2CH2CH2-Si ≡， 0.23ppm(broad s, 9H):<Analysis Results> a) Elemental analysis b) 1 H-NMR spectrum analysis chemical shift (δ) 4.65 to 4.85 ppm (broad s, 3H): ≡Si- H , 3.42ppm (s, 6H): -SiCH 3- (OC H 3 ) 2 , 1.1 ~ 1.6ppm (m, 8H): (CH 3 O) 2 SiCH 3 -CH 2 C H 2 C H 2 C H 2 C H 2 CH 2 -Si ≡, 0.35 to 0.85ppm (m, 4H): (CH 3 O) 2 SiCH 3 -CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 -Si ≡, 0.23ppm (broad s, 9H):

【００８８】[0088]

【化５７】 0.15ppm(s, 3H):[Chemical 57] 0.15ppm (s, 3H):

【００８９】[0089]

【化５８】 [Chemical 58]

【００９０】0.05ppm(s, 3H): (CH3O)2SiCH 3- c) ＩＲスペクル分析0.05 ppm (s, 3H): (CH 3 O) 2 SiC H 3 -c) IR spectrum analysis

【００９１】[0091]

【化５９】 [Chemical 59]

【００９２】[0092]

【発明の効果】本発明は文献未載の新規な有機けい素化
合物およびその製造方法に関するものであり、これは前
記したように一般式INDUSTRIAL APPLICABILITY The present invention relates to a novel organic silicon compound which has not been published in the literature and a method for producing the same, which has the general formula as described above.

【００９３】[0093]

【化６０】 ［ここにＡは水素原子または -R1-Si(CH3)3-nXn （R1は
２価炭化水素基、Ｘは加水分解性基、ｎは１，２または
３）］で示される有機けい素化合物、および1,3,5,7 −
テトラメチルシクロテトラシロキサと[Chemical 60] [Wherein A is a hydrogen atom or -R 1 -Si (CH 3 ) 3-n X n (R 1 is a divalent hydrocarbon group, X is a hydrolyzable group, n is 1, 2 or 3)] Organic silicon compounds, and 1,3,5,7 −
With tetramethylcyclotetrasiloxa

【００９４】[0094]

【化６１】 （R2は２価炭化水素基、R3は水素原子またはメチル基、
Ｘ，ｎは前記に同じ）で示されるオルガノシランとを遷
移金属化合物の存在下で反応させる前記有機化合物の製
造方法を要旨とするものであるが、この有機化合物はそ
の分子中に≡Si-H基と-R1-Si(CH3)3-nXn基を有している
ので多官能性シランカップリング剤、異官能性シランカ
ップリング剤、シリコーン樹脂架橋剤の合成に特に有用
とされるというものである。[Chemical formula 61] (R 2 is a divalent hydrocarbon group, R 3 is a hydrogen atom or a methyl group,
X and n are the same as those described above), and the gist is a method for producing the above organic compound by reacting with an organosilane represented by the formula (1) in the presence of a transition metal compound. Since it has an H group and -R 1 -Si (CH 3 ) 3-n X n group, it is particularly useful for the synthesis of polyfunctional silane coupling agents, heterofunctional silane coupling agents, and silicone resin crosslinking agents. Is to be done.

【化６２】 [Chemical formula 62]

【化６３】 [Chemical formula 63]

─────────────────────────────────────────────────────
─────────────────────────────────────────────────── ───

【手続補正書】[Procedure amendment]

【提出日】平成３年１月１８日[Submission date] January 18, 1991

【手続補正１】[Procedure Amendment 1]

【補正対象書類名】明細書[Document name to be amended] Statement

【補正対象項目名】００８０[Correction target item name] 0080

【補正方法】追加[Correction method] Added

【補正内容】[Correction content]

【００８０】[0080]

【化５４】 [Chemical 54]

【手続補正２】[Procedure Amendment 2]

【補正対象書類名】明細書[Document name to be amended] Statement

【補正対象項目名】００８１[Correction target item name] 0081

【補正方法】追加[Correction method] Added

【補正内容】[Correction content]

【００８１】[0081]

【化５５】 [Chemical 55]

【手続補正３】[Procedure 3]

【補正対象書類名】明細書[Document name to be amended] Statement

【補正対象項目名】００８５[Correction target item name] 0085

【補正方法】追加[Correction method] Added

【補正内容】[Correction content]

【００８５】[0085]

【化５６】 ─────────────────────────────────────────────────────
[Chemical 56] ─────────────────────────────────────────────────── ───

【手続補正書】[Procedure amendment]

【提出日】平成３年８月８日[Submission date] August 8, 1991

【手続補正１】[Procedure Amendment 1]

【補正対象書類名】明細書[Document name to be amended] Statement

【補正対象項目名】請求項３[Name of item to be corrected] Claim 3

【補正方法】変更[Correction method] Change

【補正内容】[Correction content]

【化２】 で示される１，３，５，７−テトラメチルシクロテトラ
シロキサンと一般式[Chemical 2] It is shown as 1,3,5,7-tetramethyl cyclotetra <br/> siloxane and Formula in

【化３】 （ここにＲ２は炭素数２以上の２価の有機基、Ｒ３は水
素原子またはメチル基、Ｘは加水分解性基、ｎは１，２
または３）で示される分子鎖末端に不飽和二重結合を有
するオルガノシランとを、遷移金属化合物の存在下で反
応させて一般式[Chemical 3] (Here, R 2 is a divalent organic group having 2 or more carbon atoms, R 3 is a hydrogen atom or a methyl group, X is a hydrolyzable group, and n is 1 or 2.
Alternatively, an organosilane having an unsaturated double bond at the end of the molecular chain represented by 3) is reacted in the presence of a transition metal compound to give a compound represented by the general formula

【化４】 ［ここにＡは水素原子または式−Ｒ１−Ｓｉ（ＣＨ３）
３−ｎＸｎ（Ｒ１は炭素数４以上の２価の有機基、Ｘは
加水分解性基、ｎは１，２または３）で示される基で、
４個のＡの中少なくとも１個は−Ｒ１−Ｓｉ（ＣＨ３）
３−ｎＸｎ基である］で示される有機けい素化合物を得
ることを特徴とする有機けい素化合物の製造方法。[Chemical 4] [Where A is a hydrogen atom or the formula -R 1 -Si (CH 3 ).
3- nXn (R 1 is a divalent organic group having 4 or more carbon atoms, X is a hydrolyzable group, and n is 1, 2 or 3),
At least one of the four A is —R 1 —Si (CH 3 ).
A 3- nXn group] is obtained. A method for producing an organic silicon compound, comprising:

【手続補正２】[Procedure Amendment 2]

【補正対象書類名】明細書[Document name to be amended] Statement

【補正対象項目名】００８１[Correction target item name] 0081

【補正方法】変更[Correction method] Change

【補正内容】[Correction content]

【００８１】[0081]

【化３５】 [Chemical 35]

【手続補正３】[Procedure 3]

【補正対象書類名】明細書[Document name to be amended] Statement

【補正対象項目名】００４５[Name of item to be corrected] 0045

【補正方法】変更[Correction method] Change

【補正内容】[Correction content]

【００４５】 [0045]

【手続補正４】[Procedure amendment 4]

【補正対象書類名】明細書[Document name to be amended] Statement

【補正対象項目名】００４７[Correction target item name] 0047

【補正方法】変更[Correction method] Change

【補正内容】[Correction content]

【００４７】[0047]

【化４０】 [Chemical 40]

【手続補正５】[Procedure Amendment 5]

【補正対象書類名】明細書[Document name to be amended] Statement

【補正対象項目名】００５１[Correction target item name] 0051

【補正方法】変更[Correction method] Change

【補正内容】[Correction content]

【００５１】[0051]

【化４４】 [Chemical 44]

【手続補正６】[Procedure correction 6]

【補正対象書類名】明細書[Document name to be amended] Statement

【補正対象項目名】００６０[Correction target item name] 0060

【補正方法】追加[Correction method] Added

【補正内容】[Correction content]

【００６０】[0060]

【化４５】 [Chemical formula 45]

【手続補正７】[Procedure Amendment 7]

【補正対象書類名】明細書[Document name to be amended] Statement

【補正対象項目名】００７２[Name of item to be corrected] 0072

【補正方法】変更[Correction method] Change

【補正内容】[Correction content]

【００７２】＜分折結果＞ ａ）元素分析 Ｓｉ Ｃ Ｈ 理論値 ２８．０３％ ４０．７６％ ８．８５％ 分析値 ２８．１８％ ４０．６９％ ８．８３％ ｂ）１Ｈ−ＮＭＲスペクトル分析 化学シフト（δ） ４．６〜４．８ｐｐｍ（ｂｒｏａｄ ｓ，３Ｈ）：≡Ｓ
ｉ−Ｈ， ３．４５ｐｐｍ（ｓ，９Ｈ） ：−Ｓｉ（ＯＣ
Ｈ ３）３， １．１〜１．６ｐｐｍ（ｍ，１６Ｈ）： （ＣＨ３Ｏ）３Ｓｉ−ＣＨ２（ＣＨ ２） ８ Ｈ２−Ｓｉ
≡， ０．３〜０．８ｐｐｍ（ｍ，４Ｈ）： （ＣＨ３Ｏ）３Ｓｉ−ＣＨ ２（ＣＨ ２）８ＣＨ２−Ｓｉ
≡， ０．１５ｐｐｍ（ｂｒｏａｄ ｓ，９Ｈ）：<Results of analysis> a) Elemental analysis SiCH theoretical value 28.03% 40.76% 8.85% Analytical value 28.18% 40.69% 8.83% b) 1 H-NMR spectrum Analytical chemical shift (δ) 4.6-4.8 ppm (broads, 3H): ≡S
i- H , 3.45 ppm (s, 9H): -Si (OC
H 3) 3, 1.1~1.6ppm (m , 16H): (CH 3 O) 3 Si-CH 2 (C H 2) 8 H 2 -Si
≡, 0.3~0.8ppm (m, 4H) : (CH 3 O) 3 Si-C H 2 (C H 2) 8 CH 2 -Si
≡, 0.15 ppm (broad s, 9H):

【手続補正８】[Procedure Amendment 8]

【補正対象書類名】明細書[Document name to be amended] Statement

【補正対象項目名】００８３[Name of item to be corrected] 0083

【補正方法】変更[Correction method] Change

【補正内容】[Correction content]

【００８３】ついで、この混合物を蒸留したところ、沸
点１４５〜１４２℃／３Ｔｏｒｒで無色透明の液体１６
５．３ｇ（収率５４．９％）が得られ、このものはガス
クロマトグラフ分析で純度９７．５％であることが確認
された。これは粘度５．２３ｃＳ、比重１．００１，
屈折率１．４４２０という物性を示した。Then, the mixture was distilled to obtain a colorless transparent liquid 16 having a boiling point of 145 to 142 ° C./3 Torr.
5.3 g (54.9% yield), this compound was confirmed to be 97.5% pure by gas chromatographic analysis. It has a viscosity of 5.23 cS, a specific gravity of 1.001,
It exhibited a physical property of a refractive index of 1.4420.

【手続補正９】[Procedure Amendment 9]

【補正対象書類名】明細書[Document name to be amended] Statement

【補正対象項目名】００９３[Correction target item name] 0093

【補正方法】変更[Correction method] Change

【補正内容】[Correction content]

【００９３】[0093]

【化６０】 ［ここにＡは水素原子または−Ｒ１−Ｓｉ（ＣＨ３）３
−ｎＸｎ（Ｒ１は２価炭化水素基、Ｘは加水分解性基、
ｎは１，２または３）］で示される有機けい素化合物、
および１，３，５，７−テトラメチルシクロテトラシロ
キサンと[Chemical 60] [Where A is a hydrogen atom or -R 1 -Si (CH 3 ) 3
-NXn (R 1 is a divalent hydrocarbon group, X is a hydrolyzable group,
n is 1, 2, or 3)], an organic silicon compound,
And 1,3,5,7 and tetramethylcyclotetrasiloxane white <br/> hexa down

【手続補正書】[Procedure amendment]

【提出日】平成４年５月１３日[Submission date] May 13, 1992

【手続補正１】[Procedure Amendment 1]

【補正対象書類名】明細書[Document name to be amended] Statement

【補正対象項目名】図面の簡単な説明[Name of item to be corrected] Brief description of the drawing

【補正方法】追加[Correction method] Added

【補正内容】[Correction content]

【図面の簡単な説明】[Brief description of drawings]

【図１】図１は、本発明の実施例１で得られた有機けい
素化合物のＮＭＲスペクトル分析の結果を示した図であ
る。FIG. 1 is a diagram showing the result of NMR spectrum analysis of an organic silicon compound obtained in Example 1 of the present invention.

【図２】図２は、本発明の実施例１で得られた有機けい
素化合物のＩＲスペクトル分析の結果を示した図であ
る。FIG. 2 is a diagram showing a result of IR spectrum analysis of the organic silicon compound obtained in Example 1 of the present invention.

Claims (4)

【特許請求の範囲】[Claims] 【請求項１】一般式 【化１】 ［ここにＡは水素原子または式-R1-Si-(CH3)3-nXn (R1
は炭素数４以上の２価の有機基、Ｘは加水分解性基、ｎ
は１，２または３）で示される基で、４個のＡの中少な
くとも１個は-R1-Si-(CH3)3-nXn 基である］で示される
有機けい素化合物。1. A general formula: [Where A is a hydrogen atom or the formula -R 1 -Si- (CH 3 ) 3-n X n (R 1
Is a divalent organic group having 4 or more carbon atoms, X is a hydrolyzable group, n
Is a group represented by 1, 2 or 3), and at least one of the four A is a -R 1 -Si- (CH 3 ) 3-n X n group]. 【請求項２】加水分解性基（Ｘ）がアルコキシ基である
請求項１に記載した有機けい素化合物。2. The organosilicon compound according to claim 1, wherein the hydrolyzable group (X) is an alkoxy group. 【請求項３】式 【化２】 で示される1,3,5,7-テトラメチルシロキサンと一般式 【化３】 （ここにR2は炭素数２以上の２価の有機基、R3は水素原
子またはメチル基、Ｘは加水分解性基、ｎは１，２また
は３）で示される分子鎖末端に不飽和二重結合を有する
オルガノシランとを、遷移金属化合物の存在下で反応さ
せて一般式 【化４】 ［ここにＡは水素原子または式-R1-Si(CH3)3-nXn（R1は
炭素数４以上の２価の有機基、Ｘは加水分解性基、ｎは
１，２または３）で示される基で、４個のＡの中少なく
とも１個は-R1-Si(CH3)3-nXn基である］で示される有機
けい素化合物を得ることを特徴とする有機けい素化合物
の製造方法。3. The formula: 1,3,5,7-tetramethylsiloxane represented by the general formula (Wherein R 2 is a divalent organic group having 2 or more carbon atoms, R 3 is a hydrogen atom or a methyl group, X is a hydrolyzable group, and n is 1, 2 or 3) and unsaturated at the end of the molecular chain. An organosilane having a double bond is reacted in the presence of a transition metal compound to give a compound represented by the general formula: [Where A is a hydrogen atom or a formula -R 1 -Si (CH 3 ) 3-n X n (R 1 is a divalent organic group having 4 or more carbon atoms, X is a hydrolyzable group, and n is 1, 2 or Or at least one of the four A in the group represented by 3) is a -R 1 -Si (CH 3 ) 3-n X n group]. A method for producing an organic silicon compound. 【請求項４】遷移金属が白金、ロジウム、ルテニウム、
パラジウムから選択されるものである請求項３に記載し
た有機けい素化合物の製造方法。4. The transition metal is platinum, rhodium, ruthenium,
The method for producing an organic silicon compound according to claim 3, which is selected from palladium.
JP3017164A 1991-01-17 1991-01-17 Organosilicon compound and production thereof Pending JPH054995A (en)

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JPH054995A true JPH054995A (en) 1993-01-14

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Cited By (11)

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JPS5291886A (en) * 1976-01-29 1977-08-02 Asahi Chem Ind Co Ltd Cephalosporins and their preparation
JP2000026610A (en) * 1998-03-30 2000-01-25 Bayer Ag Boron-and/or aluminum-containing mixture, composite material and coating
EP1013656A2 (en) * 1998-12-21 2000-06-28 Dow Corning Corporation A cyclic organosilicon endcapper having one siliconbonded hydrogen atom
JP2001525833A (en) * 1997-05-23 2001-12-11 バイエル・アクチエンゲゼルシヤフト Organosilane-oligomer
JP2005523980A (en) * 2002-05-01 2005-08-11 ダウ・コーニング・コーポレイション Organohydrogen silicon compound
JP2005529989A (en) * 2002-05-01 2005-10-06 ダウ・コーニング・コーポレイション Composition with improved bath life
US7312296B2 (en) * 2002-08-21 2007-12-25 Shin-Etsu Chemical Co., Ltd. Silicone adhesive and adhesive film
US7381457B2 (en) 2000-09-20 2008-06-03 Taisei Lamick Co., Ltd. Structure, method, and device for splicing laminated films
JP2016160285A (en) * 2015-02-26 2016-09-05 旭化成株式会社 Photocurable resin composition and method for producing the same
WO2016170851A1 (en) * 2015-04-20 2016-10-27 信越化学工業株式会社 Hydrolyzable-silyl-group-containing cyclic organohydrogen siloxane
WO2023181864A1 (en) * 2022-03-24 2023-09-28 Ａｇｃ株式会社 Compound, composition, surface treatment agent, article and method for producing article

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5133540A (en) * 1974-09-17 1976-03-22 Tokyo Shibaura Electric Co Fet zofukuki no ratsushudenryuboshikairo
JPS57137355A (en) * 1981-02-17 1982-08-24 Shin Etsu Chem Co Ltd Organopolysiloxane composition
JPH03233355A (en) * 1989-12-27 1991-10-17 Toray Dow Corning Silicone Co Ltd Filler for liquid chromatography

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5133540A (en) * 1974-09-17 1976-03-22 Tokyo Shibaura Electric Co Fet zofukuki no ratsushudenryuboshikairo
JPS57137355A (en) * 1981-02-17 1982-08-24 Shin Etsu Chem Co Ltd Organopolysiloxane composition
JPH03233355A (en) * 1989-12-27 1991-10-17 Toray Dow Corning Silicone Co Ltd Filler for liquid chromatography

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Publication number Priority date Publication date Assignee Title
JPS5814440B2 (en) * 1976-01-29 1983-03-18 旭化成株式会社 Cephalosporins
JPS5291886A (en) * 1976-01-29 1977-08-02 Asahi Chem Ind Co Ltd Cephalosporins and their preparation
JP2001525833A (en) * 1997-05-23 2001-12-11 バイエル・アクチエンゲゼルシヤフト Organosilane-oligomer
JP2000026610A (en) * 1998-03-30 2000-01-25 Bayer Ag Boron-and/or aluminum-containing mixture, composite material and coating
EP1013656A2 (en) * 1998-12-21 2000-06-28 Dow Corning Corporation A cyclic organosilicon endcapper having one siliconbonded hydrogen atom
EP1013656A3 (en) * 1998-12-21 2001-11-14 Dow Corning Corporation A cyclic organosilicon endcapper having one siliconbonded hydrogen atom
US7381457B2 (en) 2000-09-20 2008-06-03 Taisei Lamick Co., Ltd. Structure, method, and device for splicing laminated films
US8281839B2 (en) 2000-09-20 2012-10-09 Taisei Lamick Co., Ltd. Coupling structure, coupling process and coupling apparatus of laminate film
US7960002B2 (en) 2000-09-20 2011-06-14 Taisei Lamick Co., Ltd. Coupling structure, coupling process and coupling apparatus of laminate film
JP4744139B2 (en) * 2002-05-01 2011-08-10 ダウ・コーニング・コーポレイション Cured coating and preparation method thereof
JP2010285628A (en) * 2002-05-01 2010-12-24 Dow Corning Corp Composition having improved bath life
JP2005529989A (en) * 2002-05-01 2005-10-06 ダウ・コーニング・コーポレイション Composition with improved bath life
JP4755824B2 (en) * 2002-05-01 2011-08-24 ダウ・コーニング・コーポレイション Organohydrogen silicon compound
JP2005523980A (en) * 2002-05-01 2005-08-11 ダウ・コーニング・コーポレイション Organohydrogen silicon compound
US7312296B2 (en) * 2002-08-21 2007-12-25 Shin-Etsu Chemical Co., Ltd. Silicone adhesive and adhesive film
JP2016160285A (en) * 2015-02-26 2016-09-05 旭化成株式会社 Photocurable resin composition and method for producing the same
WO2016170851A1 (en) * 2015-04-20 2016-10-27 信越化学工業株式会社 Hydrolyzable-silyl-group-containing cyclic organohydrogen siloxane
JP2016204287A (en) * 2015-04-20 2016-12-08 信越化学工業株式会社 Cyclic organohydrogensiloxane containing hydrolyzable silyl group
WO2023181864A1 (en) * 2022-03-24 2023-09-28 Ａｇｃ株式会社 Compound, composition, surface treatment agent, article and method for producing article

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