JPH04208292A - N-butyl-thexyl-di-methoxysilane - Google Patents
N-butyl-thexyl-di-methoxysilaneInfo
- Publication number
- JPH04208292A JPH04208292A JP2334568A JP33456890A JPH04208292A JP H04208292 A JPH04208292 A JP H04208292A JP 2334568 A JP2334568 A JP 2334568A JP 33456890 A JP33456890 A JP 33456890A JP H04208292 A JPH04208292 A JP H04208292A
- Authority
- JP
- Japan
- Prior art keywords
- butyl
- compound
- methoxysilane
- silane
- thexyl
- 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.)
- Granted
Links
- 239000000126 substance Substances 0.000 claims description 5
- NGCDRNFHUKCMQO-UHFFFAOYSA-N butyl-(2,3-dimethylbutan-2-yl)-dimethoxysilane Chemical compound CCCC[Si](OC)(OC)C(C)(C)C(C)C NGCDRNFHUKCMQO-UHFFFAOYSA-N 0.000 claims 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract description 17
- 229910000077 silane Inorganic materials 0.000 abstract description 14
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract description 11
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 239000000654 additive Substances 0.000 abstract description 3
- 230000000996 additive effect Effects 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 238000006116 polymerization reaction Methods 0.000 abstract description 3
- 150000001336 alkenes Chemical class 0.000 abstract description 2
- 239000004567 concrete Substances 0.000 abstract description 2
- 239000004579 marble Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002023 wood Substances 0.000 abstract description 2
- UVGKQRAGAYVWQV-UHFFFAOYSA-N 2,3-dimethylbutan-2-yl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C(C)(C)C(C)C UVGKQRAGAYVWQV-UHFFFAOYSA-N 0.000 abstract 1
- 239000004566 building material Substances 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- -1 silane compound Chemical class 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- NGCRXXLKJAAUQQ-UHFFFAOYSA-N undec-5-ene Chemical compound CCCCCC=CCCCC NGCRXXLKJAAUQQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- UEIGCUVBKYUAIJ-UHFFFAOYSA-N [Li]C(CCC)CCCC Chemical compound [Li]C(CCC)CCCC UEIGCUVBKYUAIJ-UHFFFAOYSA-N 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Landscapes
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Polymerization Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、文献未載の新規な上記式（１）で表されるｎ
−プチルーテキシルージーメトキシシランに関するもの
である。[Detailed Description of the Invention] [Industrial Application Field] The present invention is directed to the novel n
- relates to petit-lutexy-methoxysilane.
本発明のシランは、５Ｌ−０−ＣＨｓの加水分解性なら
びにテキシル基及びブチル基の嵩高い有機基の特性を生
かして、木材、コンクリート、大理石等の建築物の表面
撥水処理剤として応用される。The silane of the present invention takes advantage of the hydrolyzability of 5L-0-CHs and the bulky organic groups of thexyl and butyl groups, and can be applied as a water-repellent treatment agent for the surface of buildings such as wood, concrete, and marble. Ru.
また、金属Ｍｇ、、Ｔｉ及びＡ１化合物と配位化合物を
作り易いので、この化合物はオレフィン重合用錯体触媒
の添加剤として利用でき条。In addition, since it is easy to form a coordination compound with metal Mg, Ti, and A1 compounds, this compound can be used as an additive for complex catalysts for olefin polymerization.
［従来の技術及び課題］
従来、テキシル基及びブチル基がけい素原子に結合した
メトキシシランは知られていなかった。[Prior Art and Problems] Conventionally, methoxysilane in which a thexyl group and a butyl group are bonded to a silicon atom has not been known.
本発明はこのシラン化合物を提供しようとするものであ
る。The present invention seeks to provide this silane compound.
［課題を解決するための手段］
すなわち、本発明は式
％式％
で表わされるｎ−プチルーテキシルージーメトキシシラ
ン、を要旨とするものである。[Means for Solving the Problems] That is, the gist of the present invention is n-butyl-texyl-di-methoxysilane represented by the formula %.
以下に本発明について詳しく説明する。The present invention will be explained in detail below.
本発明の前記式（１）で示されるｎ−プチルーテキシル
ージーメトキシシランは次の方法により合成できること
が分った。−法はテキシルートリーメトキシシランとｎ
−ブチルリチウムを反応させる方法であり、また、他の
一法はテキシルートリーハライドシランとｎ−ブチルリ
チウムを反応させて一度ｎ−プチルーテキシルージーハ
ライドシランを合成した後に、これをメタノールと反応
させる方法である。It has been found that the n-butyl-butexyl-di-methoxysilane represented by the formula (1) of the present invention can be synthesized by the following method. - The method is texyltrimethoxysilane and n
Another method is to react texyl-butyl lithium with n-butyl lithium to synthesize n-butyl-butyl lithium, and then react it with methanol. This is the way to do it.
上記の合成反応に際して、原料シランはそのままあるい
は溶液として用いることができる。溶液とする場合の溶
媒にはテトラハイドロフラン、ジエチルエーテル、ジブ
チルエーテル、ペンタン、ヘキサン等が例示される。シ
ラン濃度としては０．０１モル／ｊ２以上とすればよい
。また、ｎ−ブチルリチウムは溶液として用いるのがよ
く、溶媒としてはテトラハイドロフラン、ジエチルエー
テル、ジブチルエーテル、ベンクン、ヘキサン等が例示
される。ｎ−ブチルリチウムの濃度は０．Ｏ１〜４モル
／ρとすればよい。In the above synthesis reaction, the raw material silane can be used as it is or as a solution. Examples of solvents used in a solution include tetrahydrofuran, diethyl ether, dibutyl ether, pentane, and hexane. The silane concentration may be 0.01 mol/j2 or more. Further, n-butyllithium is preferably used in the form of a solution, and examples of the solvent include tetrahydrofuran, diethyl ether, dibutyl ether, benzune, and hexane. The concentration of n-butyllithium is 0. It may be set to 1 to 4 moles of O/ρ.
合成反応を行なうには、上記シランあるいはシラン溶液
にｎ−ブチルリチウムを添加してゆくか、又は、ｎ−ブ
チルリチウムにシランあるいはシラン溶液を加えてゆき
、−７８℃〜１００℃で反応させればよい。反応終了後
、副生じたリチウム塩を濾過して取り除き、溶媒を留去
してから蒸留することにより、ｎ−プチルーテキシルー
ジーメトキシシランもしくはｎ−プチルーテキシルージ
ーハライドシランを得る。To carry out the synthesis reaction, either n-butyllithium is added to the above silane or silane solution, or silane or silane solution is added to n-butyllithium, and the reaction is carried out at -78°C to 100°C. Bye. After the reaction is completed, the by-produced lithium salt is removed by filtration, the solvent is distilled off, and then distilled to obtain n-butyl-butyl-thexyl-di-methoxysilane or n-butyl-butyl-texyl-di-halide silane.
後者のｎ−プチルーテキシルージーハライドシランを２
当量以上のメタノールと反応させればｎ−プチルーテキ
シルージーメトキシシランが得られる。The latter n-butylene-butylene-loosy halide silane was added to 2
By reacting with methanol or more in an equivalent amount, n-butyl-butyl-texyl-di-methoxysilane can be obtained.
［実施例］ 次に、実施例により本発明を具体的に説明する。[Example] Next, the present invention will be specifically explained with reference to Examples.
実施例１
１．６モル／βのブチルリチウムを含有するテトラハイ
ドロフラン溶液０．２１βをテキシルートリークロロシ
ラン０．４７モル（１０３，５ｇ）を含むテトラハイド
ロフラン０．１βに、反応温度−７８℃〜１０℃にて５
時間かけて滴下した。その後反応温度を徐々に２５℃ま
で上げた。ガスクロマトグラフィーにより反応の終点を
確認した後、副生じた塩を濾過により取り除き、さらに
溶媒を蒸留により除去した。この溶媒を留去した濃縮物
を減圧蒸留（１０３℃／ ５ ｍｍＨｇ） して無色透
明の液状物質３２ｇを得た。Example 1 0.21β of a tetrahydrofuran solution containing 1.6 mol/β of butyllithium was added to 0.1β of tetrahydrofuran containing 0.47 mol (103.5 g) of texyltrichlorosilane at a reaction temperature of -78 5 at ℃~10℃
It dripped over time. Thereafter, the reaction temperature was gradually raised to 25°C. After confirming the end point of the reaction by gas chromatography, the by-product salt was removed by filtration, and the solvent was further removed by distillation. The concentrate obtained by distilling off the solvent was distilled under reduced pressure (103°C/5 mmHg) to obtain 32 g of a colorless and transparent liquid substance.
この得られた物質１０ｇを１，５−ジアザビシクロ［５
，４，Ｏｌ ウンデク−５−エン（Ｄ Ｂ Ｕ） １３
ｇ （８６ミリモル）、ヘキサン５０ｍＩ２及びメタノ
ール３．０ｇ（９４ミリモル）の混合物中に２５℃で滴
下し２時間反応させた。ガスクロマトグラフィーにより
反応の終点を確認した後、副生じたＤＢＵ塩酸塩を濾過
により取り除き、さらに溶媒を蒸留により除去した。こ
の溶媒を留去した濃縮物を減圧蒸留（８６’Ｃ／ ３
ｍｍＨｇ） シて無色透明の液状物質７．５ｇを得た。10 g of this obtained material was added to 1,5-diazabicyclo[5
,4,Ol undec-5-ene (DBU) 13
g (86 mmol), 50 ml of hexane and 3.0 g (94 mmol) of methanol at 25°C and reacted for 2 hours. After confirming the end point of the reaction by gas chromatography, the by-produced DBU hydrochloride was removed by filtration, and the solvent was further removed by distillation. The concentrate from which the solvent was distilled off was distilled under reduced pressure (86'C/3
mmHg) to obtain 7.5 g of a colorless and transparent liquid substance.
ガスクロマトグラフィーによる分析の結果は、この液状
物質が単一成分であることを示した。このものの２５℃
における屈折率は１．４３９８であった。Analysis by gas chromatography showed that this liquid material was single component. 25℃ of this
The refractive index was 1.4398.
さらに、ガスクロマトグラフィー質量分析、＋Ｈ−ＮＭ
Ｒ分析の結果は下記のとおりであった。Furthermore, gas chromatography mass spectrometry, +H-NM
The results of the R analysis were as follows.
ガスクロマトグラフィー質量分析
分子イオンピーク（Ｍ／Ｚ） ： ２３２’Ｈ−Ｎ Ｍ
Ｒ分析（ＣＤＣＩｓ）
δ（ｐｐｍ）：３．５７ （ｓ、６Ｈ，−０ＣＨ３）２
．２〜１．１ （ｍ、５８．−ＣＨ２−、−ＣＨ）１．
１〜０．５ （ｍ、１７ｔ（、−ＣＨ３，５ｔ−ＣＨ２
）また、赤外線吸収スペクトル分析の結果は第１図に示
すとおりであった。Gas chromatography mass spectrometry molecular ion peak (M/Z): 232'H-NM
R analysis (CDCIs) δ (ppm): 3.57 (s, 6H, -0CH3)2
．． 2-1.1 (m, 58.-CH2-, -CH)1.
1 to 0.5 (m, 17t(, -CH3,5t-CH2
) Furthermore, the results of infrared absorption spectrum analysis were as shown in FIG.
以上の分析結果から、得られた物質は Ｃ）１３ ＣＨ。From the above analysis results, the obtained substance is C) 13 CH.
の構造をもつｎ−プチルーテキシルージーメトキシシラ
ンであることが確認された。（総合単離収率３１％）
実施例２
１．６モル／Ｉ２のブチルリチウムを含有するテトラハ
イドロフラン溶液６ｍβをテキシルートリーメトキシシ
ラン２．０ｇ （１０ミリモル）を含むテトラハイドロ
フラン１０ｍβ溶液に、反応温度−７８℃〜２０℃にて
４時間で滴下した。その後２５℃まで温度を上げて反応
させた。ガスクロマトグラフィーにより反応の終点を確
認した後、副生じた塩を濾過により取り除き、さらに溶
媒を蒸留により除去した。この溶媒を留去した濃縮物を
減圧蒸留して無色透明の液状物質１．４ｇを得た。分析
結果は実施例１で得られたｎ−プチルーテキシルージー
メトキシシランに一致した。（単離収率６３％）［発明
の効果］
本発明により文献未載の新規なシラン化合物であるｎ−
プチルーテキシルージーメトキシシランが提供された。It was confirmed that it was n-butyl-butyl-thexyl-methoxysilane having the structure. (Overall isolated yield 31%) Example 2 A 6 mβ solution of tetrahydrofuran containing 1.6 mol/I2 of butyllithium was added to a 10 mβ solution of tetrahydrofuran containing 2.0 g (10 mmol) of texyltrimethoxysilane. The mixture was added dropwise over 4 hours at a reaction temperature of -78°C to 20°C. Thereafter, the temperature was raised to 25°C to cause a reaction. After confirming the end point of the reaction by gas chromatography, the by-product salt was removed by filtration, and the solvent was further removed by distillation. The concentrate obtained by distilling off the solvent was distilled under reduced pressure to obtain 1.4 g of a colorless and transparent liquid substance. The analysis results were consistent with the n-butyl-butexyl-methoxysilane obtained in Example 1. (Isolated yield 63%) [Effects of the invention] The present invention has produced a novel silane compound, n-
Petit lute xy methoxysilane was provided.
このシランは建築物の表面撥水処理剤やすレフイン重合
用錯体触媒の添加剤として有用である。This silane is useful as a water repellent agent for the surface of buildings and as an additive for complex catalysts for reflex polymerization.
第１図は本発明の実施例１で得られたシランの赤外線吸
収スペクトルを示す図である。FIG. 1 is a diagram showing the infrared absorption spectrum of the silane obtained in Example 1 of the present invention.
Claims (1)
ン。[Claims] 1. n-butyl-thexyl-di-methoxysilane represented by the formula ▲ Numerical formulas, chemical formulas, tables, etc. are available.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2334568A JPH0813827B2 (en) | 1990-11-30 | 1990-11-30 | n-butyl-thexyl-di-methoxysilane |
| US07/798,515 US5136072A (en) | 1990-11-30 | 1991-11-26 | Thexyl C1 -C4 alkyl dialkoxy silane |
| EP91311071A EP0488759B1 (en) | 1990-11-30 | 1991-11-29 | Thexyl (C1-C4)alkyl dialkoxy silanes; methods of preparation; and uses thereof |
| DE69103388T DE69103388T2 (en) | 1990-11-30 | 1991-11-29 | Thexyl- (C1-C4) alkyl-dialkoxysilanes, process for their preparation and their use. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2334568A JPH0813827B2 (en) | 1990-11-30 | 1990-11-30 | n-butyl-thexyl-di-methoxysilane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04208292A true JPH04208292A (en) | 1992-07-29 |
| JPH0813827B2 JPH0813827B2 (en) | 1996-02-14 |
Family
ID=18278860
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2334568A Expired - Fee Related JPH0813827B2 (en) | 1990-11-30 | 1990-11-30 | n-butyl-thexyl-di-methoxysilane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0813827B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10227427B2 (en) * | 2014-01-17 | 2019-03-12 | Borealis Ag | Process for preparing propylene/1-butene copolymers |
| WO2023181867A1 (en) * | 2022-03-24 | 2023-09-28 | Ａｇｃ株式会社 | Compound, composition, surface treatment agent, article manufacturing method, and article |
-
1990
- 1990-11-30 JP JP2334568A patent/JPH0813827B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10227427B2 (en) * | 2014-01-17 | 2019-03-12 | Borealis Ag | Process for preparing propylene/1-butene copolymers |
| WO2023181867A1 (en) * | 2022-03-24 | 2023-09-28 | Ａｇｃ株式会社 | Compound, composition, surface treatment agent, article manufacturing method, and article |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0813827B2 (en) | 1996-02-14 |
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