JPS6242993A - Bis(3-acyloxypropyl)dialkoxysilane - Google Patents
Bis(3-acyloxypropyl)dialkoxysilaneInfo
- Publication number
- JPS6242993A JPS6242993A JP60182545A JP18254585A JPS6242993A JP S6242993 A JPS6242993 A JP S6242993A JP 60182545 A JP60182545 A JP 60182545A JP 18254585 A JP18254585 A JP 18254585A JP S6242993 A JPS6242993 A JP S6242993A
- Authority
- JP
- Japan
- Prior art keywords
- group
- reaction
- compound
- acyloxypropyl
- absorption
- 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
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 17
- -1 3-acetoxypropyl Chemical group 0.000 abstract description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 5
- 150000003839 salts Chemical class 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 5
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 2
- 230000000704 physical effect Effects 0.000 abstract description 2
- 229920002545 silicone oil Polymers 0.000 abstract description 2
- 239000002966 varnish Substances 0.000 abstract description 2
- 239000006087 Silane Coupling Agent Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000010521 absorption reaction Methods 0.000 description 16
- 238000000034 method Methods 0.000 description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- 239000002184 metal Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 150000003961 organosilicon compounds Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000005311 nuclear magnetism Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- FYNJWLOOBINARS-UHFFFAOYSA-N 3-chlorooctane Chemical compound CCCCCC(Cl)CC FYNJWLOOBINARS-UHFFFAOYSA-N 0.000 description 1
- LYJHVEDILOKZCG-UHFFFAOYSA-N Allyl benzoate Chemical compound C=CCOC(=O)C1=CC=CC=C1 LYJHVEDILOKZCG-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 102100026197 C-type lectin domain family 2 member D Human genes 0.000 description 1
- 235000017788 Cydonia oblonga Nutrition 0.000 description 1
- 241000410518 Cyrano Species 0.000 description 1
- OVBPIULPVIDEAO-LBPRGKRZSA-N Folic acid Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 1
- 101000912615 Homo sapiens C-type lectin domain family 2 member D Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000011387 Li's method Methods 0.000 description 1
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000000451 chemical ionisation Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229960000304 folic acid Drugs 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Abstract
Description
〈産業上の利用分野〉
本発明は新規な有機ケイ素化合物に関するものである。
〈従来の技術〉
3−アシロキシプロピル基を有する有機ケイ素化合物、
例えば3−アシロキノブロピルアルキルレアルコキシシ
ラン、3−アンロキシプロピルトリアルコキシシラ7等
は公知であり、それらは変性ンリコーンオイルの1帛ネ
Iとして使用できるほかフラン力ノブリング剤として利
用でき、またアルキレンアルキルアクリl/−1・共重
合体に対して水分架橋剤として作用することが公知であ
る(米国特許第4.291. I 36 fj明細M)
。
〈発明が解決しようとする問題点ミ〉
しかしながら、従来の3−アシ(+キシプロピルアルコ
キシンラフ類を原ネ」とした変V1:ンリニ]−ノ・オ
イル争ワニスを化粧品、ワックス、電気絶縁油、捏水剤
、塗i−1、離型剤、消泡剤、潤滑油の基剤として用い
た場合には親油性等の物性について問題があり、まt:
従来の3−アンロキンプロビルアルコキシンラン類をフ
ラン力・ノブリング剤、水分架橋剤として用いた場合に
は接着性、表面改質能及び処理後の硬度等が低いという
欠点があった。
〈問題点を解決するための手段および作用〉本発明者ら
は以トの、ような従来技術の欠点を解消することを目的
として鋭意研究した結束、変性ンリコ−7・オイJl・
リースとした場合に親油性等の物V1を向I−゛せしめ
ると同時にシラ5・カップリンク剤、水分架橋剤としt
二場合に表面改質能、接着V1および処理後の硬度を向
上せしめることができる新規な3−アント3キンブ11
ビルアルフキシシラノ類を見出し本発明に到達した。
すなわち、本発明は次の一般式
%式%
〔式中、Rは水素原子又は炭素原子数1〜20個のアル
キル基もしくはアリール基、R1は炭素原子数1〜5個
のアルキル基又はアルコAンアルキル基を示す〕で示さ
第1るヒス(3−アシロキシプロピル)ノアルコキンシ
ラッである。
前記一般式中、Rは水素原子又は炭素原子数1〜20個
のアルキル基もしくはアリール基を示し、具体的には水
素側−rのほかメチル基、エチル基、n−プロピル基、
1S(1−プロピル基、n−エチル基、5ec−ブチル
基、1so−ブチルg、l:crt−ブチル基、n−ヘ
ゾタテノル基、)90ヘキノル基、4−メチルノシ(]
]/\A−/ル基の鎖状及び環状の炭素1+%了数1
−20個の叱肪族炭化水素基やフェニル基のほか4−メ
ナノ1フェニル?tu、4−ンクL]ヘキンル7エール
基、2 、4−−ノメチルフゴール基等のすくなく ト
ム1個以1の鎖状及び環状の脂肪族炭化1水素基が4)
°再環に置換しt、x炭素原子数1〜20個のアリール
基か挙げら第1る。
また前記一般式中、R1は炭素原−f数1〜5個のアル
キル基又はアルニ】キノアルキル)& ヲi’iζし、
具体的にはメチル基、エチル%、n−−frJビル基、
iso −=f IIビル基、n−−エチル基、SCI
’ −エチル基、iso −−)チJl/ 基、+er
t−iデル基等の炭素原子数1〜5個の鎖状アルキルJ
、(やメトキシエチル基、工l・キシエチルノ氏等の炭
素原子数の合d1が1〜5個の鎖状アル:1キシアット
キル基を好ましく挙げることができる。
本発明化白物の好ましいVL体的な例としてはrTTc
O,(CT(2)3J2 Si (ocH,、)2 、
r TTCO2(CH,! ) 3 ]2 S i (
OBun) 2 、rCILCO□(CI−L)、、
−】2Si(OCH,t)i 、rCH,CO,(C
T1.)3]2 Si (QC21T、)2 、〔CI
lIC07(CIい、」、、 5i(OCII(CTT
:+)z)2、〔CTl1CO3(CTT2)j〕2S
1(OI〕Y6)2、[CIL CO,(CJL )
+′□]、、 S 1rOc(cH,+)a〕z、rC
I■、C04(C[い+12Si(OBu’)7、[C
T−T、CIしC(’)、(CIL)332Si (O
CTIl)2 、c CI(、< CiL ) l l
、C02(CTい] :1. S i (0OT+ )
2 、cClLCH,Co、 (CTL)、h S
i (OBLIn)2、〔CH,(CTL)+aCO
z’(CI’Ll)、〕2si (OCHII)2
、cPhC02(CJL):+]2Si (OCIL)
2 。
(PhCO,(CILh〕2Si(OBu”)2、cH
co、(CTL):+h Si (OCH2C,H,,
0CT(、)企 、[CFLCo□(CTい+ ]2S
i (OCH2(NT20CTr、 ) 2.1CT
(jCO,、(CH,)、、 112 S i (OC
H,、CTT2QC2T−T5) 2、(’PliCC
)、 (CH2) 3 )2 S 1(OCL o■2
ocri、、 )2、本発明の化合物は任意の方法で製
造することができる。本発明化合物の製造法としては、
例えば、
西 ヒス(3−アシロキシプロピル)ンクロロンランヲ
アルコール又はアルコキー・J& 4r 分子内にイ1
−#るアルコールと反応させるli法、顔 ヒス(3−
アシロキンゾロビル)二ノ勺「1[]シラノをアルコー
ル又はアルコキン基を分子内に有するアルコールの金属
塩と反応させる方法、
0 カルボン酸のアリル1スプルとジアルコキンンラ、
をヒドロシリル化反応さliる方法、σ) カルホン酸
の金属塩とヒス(:1−ハV1プロピル)ンアルコキン
シランを置換反応させる方法
等が挙げらねる。
以F1へのIj法に−)いて具体的に説明する。
方法においては、副生する塩酸を中和する目的で、アε
゛/類を反応系に導入することもできる。
その場合は、生成するアミンの塩酸塩のj二め攪拌が困
難になる場合がJ)るので、ベンセン、キンレノ、トノ
レノノ、1−チル・、′I″HF 、ヘキ→lノ、石油
ゴーチル、リグロイン等を反応溶媒として使用するのが
望ましい。
反応は、原木゛1、反応剤を溶媒中で配合攪拌−孝るこ
とに34り実施できる。
ヒス(3−アンr+ 4ノブロビル)ノウロロノラント
アルコール叉はアルコAノ基を分子内に有するアルコー
ル又はその金属塩は、いかなる比率(モル比)でも反応
させることか可能であるが、好ましくは反応を完全に行
なわせしめるためにl:2(モル比)以1−で反応させ
る。
反応温度は一30〜150℃であり、好ましくは0〜l
Q O’Cである。
反応時間は反応溶媒量、反応温度、原木1[ル比等に、
しって0.1〜300hrの範囲でかえることが可能で
ある。
反応は常用下又は加圧下のいず第1でも実施することが
できる。
かくして得られた反応混合物から本発明化合物を単離す
る方法は常法によることができ、例えば減圧蒸留又はカ
ラムクロマトグラフィー等により目的物を111離、精
製することができる。
・、実施例〉
J’J下実施例によ−)で本発明の化合物を具体的に説
明するが、息子の実施例は本発明の一部の例に−〕いて
説明するものであI)、特許請求の範囲を限定するもの
でない。
実施例1
攪拌機、滴■・ロート、温度a1を装着しf:1 #の
力うス製反応器にヒス(3−アセトキノプロピル)ンク
[II]ノラシ59.3F、l−リエチルアミン66g
/、ベー・セ、、−600肩tを仕込み、10°(゛以
下に反応液温を保ち攪拌しながらメタツル15.29を
90分間で滴7−’ l、た。滴士糺−r・後、反応液
温を室温にもどし、さらに1時間攪拌を続けt:o反応
後、トリエチルアミン塩酸塩を濾過しj二のち、反応液
を蒸留して沸点141〜142℃7′151Hgの生成
物48.91を得を二 (収率85%)。
得ら11だ生成物の赤外線吸収スペクトルお、LびII
I核磁気其鳴スベクI・ルのチi−、−、−1・を第1
図および第2図にそれぞれ示しまた。赤外線吸収スベク
トルは1740m に酢酸エステルのカルボニルの吸
収、さらにl O80(’m ’ 付近ニ5i−0−C
の強い吸収を示した。またそのCDCI、 中で測定し
た核磁気共鳴スペクトルは(δ値)4.07 P (t
、4fICTTlCO2CIT、’J 、3.60 (
s、 6HS+−0CI(+ ) 、2. I O(s
、 6 HCH4C(%C)L−)、1.5〜2.
I (m、 4HCTTlCo、CTT、CT(、、
CH25i) 、0.5〜1.0 (m、 4HCTL
CO,、CJI2CH2CILSi)にシグナルを1<
シj二。
質量スヘクトルはCI法(chemical ioni
zationmethod )でイノブタンを使用した
場自は、M −+1、 = 293のピータが測定さオ
<Industrial Application Field> The present invention relates to a novel organosilicon compound. <Prior art> Organosilicon compound having a 3-acyloxypropyl group,
For example, 3-acyloquinopropylalkylrealkoxysilane, 3-anroxypropyltrialkoxysilane 7, etc. are known, and they can be used as part I of modified silicone oil as well as as a furanic knobling agent. It is also known to act as a moisture crosslinking agent for alkylenealkylacrylic l/-1 copolymers (US Pat. No. 4.291. I 36 fj Specification M).
. <Problems to be solved by the invention> However, the conventional 3-(+xypropyl alkoxine rough)-based variant V1: Nrini]-no oil and varnish cannot be used in cosmetics, waxes, and electrical insulation. When used as a base for oil, water repellent, coating i-1, mold release agent, antifoaming agent, and lubricating oil, there are problems with physical properties such as lipophilicity.
When conventional 3-anthroquineprobyl alkoxylans were used as furanic force/knobling agents and moisture crosslinking agents, there were drawbacks such as low adhesiveness, surface modification ability, and hardness after treatment. <Means and effects for solving the problems> The present inventors have intensively researched the following methods to overcome the drawbacks of the prior art:
When it is made into a lease, it makes the lipophilic substance V1 towards I-, and at the same time acts as a coupling agent and water crosslinking agent.
A novel 3-ant 3-kimbe 11 that can improve surface modification ability, adhesion V1 and hardness after treatment in two cases.
The inventors discovered biralfoxysilanos and arrived at the present invention. That is, the present invention is based on the following general formula % [wherein R is a hydrogen atom or an alkyl group having 1 to 20 carbon atoms or an aryl group, and R1 is an alkyl group having 1 to 5 carbon atoms or an alkyl group having 1 to 5 carbon atoms] This is the first his(3-acyloxypropyl)noalcoquine silane represented by the following formula. In the above general formula, R represents a hydrogen atom or an alkyl group or aryl group having 1 to 20 carbon atoms, and specifically, in addition to the hydrogen side -r, methyl group, ethyl group, n-propyl group,
1S (1-propyl group, n-ethyl group, 5ec-butyl group, 1so-butylg, l:crt-butyl group, n-hezotatenol group,) 90 hequinol group, 4-methylnocy(]
]/\A-/Number of chain and cyclic carbon atoms in the group 1 + %
-In addition to 20 aliphatic hydrocarbon groups and phenyl groups, 4-menano-1 phenyl? tu, 4-kL] hekynyl7 ale group, 2, 4-nomethyl fugol group, etc. 1 or more tom or 1 chain or cyclic aliphatic hydrocarbon monohydrogen group 4)
The first one is an aryl group having 1 to 20 carbon atoms substituted with a rearrangement. In the above general formula, R1 is an alkyl group having a carbon atom number of 1 to 5,
Specifically, methyl group, ethyl%, n--frJ building group,
iso -=f II building group, n--ethyl group, SCI
'-ethyl group, iso--)tiJl/ group, +er
Chain alkyl J having 1 to 5 carbon atoms such as t-i del group
, (, methoxyethyl group, and a chain alkyl group having a total number of carbon atoms of 1 to 5, such as a methoxyethyl group and a methoxyethyl group). An example is rTTc
O, (CT(2)3J2 Si (ocH,,)2,
r TTCO2(CH,!) 3 ]2 S i (
OBun) 2, rCILCO□(CI-L),,
−]2Si(OCH,t)i, rCH,CO, (C
T1. )3]2 Si (QC21T,)2, [CI
lIC07(CI,", 5i(OCII(CTT)
:+)z)2, [CTl1CO3(CTT2)j]2S
1 (OI] Y6) 2, [CIL CO, (CJL)
+′□],, S 1rOc(cH,+)a]z,rC
I■,C04(C[i+12Si(OBu')7,[C
T-T, CI C('), (CIL)332Si (O
CTIl)2,c CI(,<CiL) l l
, C02 (CT): 1. S i (0OT+)
2, cClLCH, Co, (CTL), hS
i (OBLIn)2, [CH, (CTL)+aCO
z'(CI'Ll),]2si (OCHII)2
, cPhC02(CJL):+]2Si (OCIL)
2. (PhCO, (CILh)2Si(OBu”)2, cH
co, (CTL):+h Si (OCH2C,H,,
0CT(,) , [CFLCo□(CT+]2S
i (OCH2(NT20CTr, ) 2.1CT
(jCO,, (CH,),, 112 S i (OC
H,,CTT2QC2T-T5) 2,('PliCC
), (CH2) 3 )2 S 1 (OCL o■2
ocri, )2, the compounds of the present invention can be produced by any method. The method for producing the compound of the present invention is as follows:
For example, Nishihis(3-acyloxypropyl)chlorone alcohol or alcoholy J & 4r has 1 in the molecule.
- Li method of reacting with alcohol, facial hissing (3-
acyloquine zolovir) Ninoki "1 [] A method of reacting cyrano with an alcohol or a metal salt of an alcohol having an alcoquine group in the molecule, 0 Allyl 1 sprue of carboxylic acid and dialcoquine,
Examples include a method in which a metal salt of carbonic acid is subjected to a hydrosilylation reaction, and a method in which a metal salt of carbonic acid is subjected to a substitution reaction with a his(:1-propyl)-alcokyne silane. The Ij method for F1 will be specifically explained below. In the method, for the purpose of neutralizing the by-produced hydrochloric acid,
/ can also be introduced into the reaction system. In that case, it may be difficult to stir the hydrochloride of the amine that is produced, so benzene, quince, 1-thyl, 'I''HF, hex→l, petroleum gothyl, It is preferable to use ligroin or the like as a reaction solvent.The reaction can be carried out by mixing and stirring raw wood and a reactant in a solvent. Alcohols or alcohols having an AlcoA group in their molecules or their metal salts can be reacted at any ratio (molar ratio), but preferably at a ratio of 1:2 (molar ratio) to ensure complete reaction. The reaction temperature is -30 to 150°C, preferably 0 to l
Q O'C. The reaction time depends on the amount of reaction solvent, reaction temperature, lumber ratio, etc.
It is possible to change the time within the range of 0.1 to 300 hr. The reaction can be carried out either under normal conditions or under pressure. The compound of the present invention can be isolated from the reaction mixture thus obtained by a conventional method. For example, the target compound can be isolated and purified by distillation under reduced pressure or column chromatography.・, Examples〉 The compounds of the present invention will be specifically explained in the following Examples, but the Examples of Son will be explained based on some examples of the present invention. ), does not limit the scope of the claims. Example 1 His(3-acetoquinopropyl)ink [II] Norashi 59.3F, 66 g of l-ethylamine was placed in a reactor made of f: 1 # forceps equipped with a stirrer, a dropping funnel, and a temperature a1.
/, Baise, -600 shoulder t was charged, and while stirring and keeping the reaction temperature below 10°, 7-'l of Metatsuru 15.29 was added dropwise in 90 minutes. After that, the temperature of the reaction solution was returned to room temperature, and stirring was continued for another 1 hour. After the reaction, triethylamine hydrochloride was filtered. After that, the reaction solution was distilled to obtain a product 48 with a boiling point of 141-142℃ 7'151Hg. .91 was obtained (yield 85%). Infrared absorption spectrum of the obtained product 11.
I-,-,-1-1 of nuclear magnetism.
and FIG. 2, respectively. The infrared absorption vector is the absorption of carbonyl of acetate ester at 1740m, and the absorption of carbonyl of acetate ester at 1740m, and the
showed strong absorption. In addition, the nuclear magnetic resonance spectrum measured in the CDCI had a (δ value) of 4.07 P (t
,4fICTTlCO2CIT,'J ,3.60 (
s, 6HS+-0CI(+), 2. I O(s
, 6HCH4C(%C)L-), 1.5-2.
I (m, 4HCTTlCo, CTT, CT(,,
CH25i), 0.5-1.0 (m, 4HCTL
CO, , CJI2CH2CILSi) with a signal of 1<
Cj2. The mass spectrum is determined using the CI method (chemical ionization method).
zationmethod) using inbutane, M −+1, = 293 Peters were measured.
【た。
以I−のテークより得られた化合物の構造は(CTTI
I C(−)2 (CH2) :+ )2 S l (
0C1I:+ ’I 2であることを確認しIこ。
実施例2
実施例1と同様の反応条件でヒス(:ウーアセトキシプ
[コピル)ジクロロシランLotとイソプロピルアルコ
ール48gを反応させて、沸点153〜154℃/ 3
mHgノ生成物9.4fを得た(収率81も)。
?iJらねた生成物の赤夕を線吸収スベクIルは、17
40 cm に醋酸ニスフルのlツルボLルh−〇)
吸収を示し−Cいる。さらに1025n(”J近に5l
−0−Cの強い吸収を示している。
またそのCDCl、中で測定し、た核磁気t(鳴スペク
トルは(δ値) 3.9〜4..4 (m、6TICI
T、CO□CJLCILCILSi(ICJf(CH,
、)2 ) 、 2. 0 6 (s 。
6 H(−11=COzCH2−) 、1.3〜2.
] (rn 、 4 ITClllCO,CfICI
(、CT(28i ) 、1.18 (d 、 +21
(S ] CF((CIT+) 2 ) 、0.3〜0
.8 (ITS、 411CIT、 C02C+I、
CJj、 CT(2S i )に、グナルを小ず。
質量スペクトルはCI法(chemicnl ioni
zationmethod )でアンモニアを使用しj
二場合、M −+18−366のピークが測定され!=
。
息子のテークより得らJ’l を1化合物は(CIT、
C02(CIL)、 :125i(OCH(CI(い、
]2で、jする、−確認しtこ。
実施例3
実施例1とい1様の反応条件でヒス(3−アセトキシブ
l]ピル)ジクロロシラノIOyと7ヂルセルノルブ5
58gを反応させて、沸点1 fi 5〜170°C,
/ 1.2翻T1gの1成物10.742fを得tこ。
得られtこノ4放物の赤夕1線吸収スベク]・ルは、1
74oz に酢酸エステルのカルボニルの吸収を示し
ている。さらに+090/m’にS】−0−Cの強い吸
収を示している。
まt−そのCDC1,中で1lll+定した核磁気JI
、鳴スペクトルは(δ値) 4.03(11,4TI)
、3.88 (L、4H) 、3.45 (1,lI
) 、3.40 (s、6II) 、2.05 (s、
6H) 、1.45〜2.OO(m。
411)、045〜090(m、4■■)にシグナルを
示す。
質量スペタトルはCI法(アンモニア)でMl−+18
=398のピークが測定さ第1た。
以上のデータより得ら才]た化合物は
c CH,Co□(Clい+ ] 2 S ] (0C
T−T2 CH20CtTい、であると確認しtこJ
実施例4
攪拌機、滴Fr1.−1、温庶ハ1を装?11)?、−
200d (D カーミス製反応器にヒス(:3−アI
!トキノプI−1ビル)ノケロロ7・9715g、1−
り丁−fノ1アζ、12y1ヘノセ−100z(をイ1
込み、10’(’ KJ十に反応at、tを保ち、攪拌
しなからterl−フタメール88〕を10分間で滴下
しt:、o滴■・終j′後、反応液温を室温にもどし、
さらに1時間攪拌し6時間乾留しj二。反応後、l−I
I−r−fルアミン塩酸塩を7濾過したのち、反応溶媒
を留去してその反応混合物をT IT F 5 z/と
ともに50m1 [11) If−7ス製反応開に加え
、T HF 5 mlにとかしtニカリウムtert−
ブトAンド(純1隻90%、1、53 y )を室温[
ζで10力間で滴下し、T ITFを留去したのち、力
→l・り「171−グラフィー(r(ieselgel
60 art、 7733 、展開溶媒:耐酸エチル
′ンクロヘキサン=■/3)で生成物1.591を単離
しt:。
得ら第1だ生成物の赤外線吸収スペクトルは+74:1
m に酢酸エステルのカルボニルの吸収をホしこいる
。さらに] 050 rys−’ ニ5i−(1−Cの
強い吸収を示している。
またCDCl、中で測定しt:核磁気te鳴スペクトル
は(δ値) 4.03 (t、4H) 、2.06 (
s。
6H) 、1.3〜2.0 (m、4H)、1.31’
(S。
18H) 、0.4〜0.9 (m、4H)にシグナル
を示す。
質量スペクトルはCI法でアンモニアを使用した場合M
+ l 8 = 394のピークが測定されtこ。
以上のデータより得られた化合物は
〔CH3Co2(CHの、)2Si rOc(cH,+
)J〕、+であると確認しtこ。
実施例5
実施例1と同様の反応条件でヒス(3−ブチロキノプロ
ピル)ジクロロシラン5.873 yとメタノール1.
] 58 yを反応させて沸点150〜154℃/
0.49 mHgノ生成物4.097 f ’i−得t
こ。
得られtコ牛放物の赤外線吸収スペクトルは1737
m−’に酪酸エステルのカルボニルの吸収、さらにI
O80nx ’付近に5i−0−Cの強い吸収を示した
。
またCI)C13中で測定しj:核磁気」[、鳴スペク
トルは(δ値)4.(12(t、4T() 、3.54
(s。
6IT) 、2.27 (L、4T() 、1.3〜2
.0 (m。
8H) 、0.5〜1..1 (m、l0H)にシグ
ナルを示しtこ。
質量スペクトルはCr 法<フ′ンモニーア〕M十18
=36(1のピークが測定されtこ。
以りのデータより得らオ]た化合物の構造はCCITI
C)L CFL C(% (CH2) 1:’ 2 S
l (0CTT:l ) 2であると確認しtこ。
実施例6
シクロロンラン導入管、アセトノードライアイス冷却器
、回転子、温度言1を装若し、アルゴン置換法の反応容
器に、安息香酸アリル10.932と塩化白金酸のイ゛
ノブロバノール溶液(a度゛2重に%)1112111
を加え、反応温度77〜88′Cに保って加熱、攪拌し
つ−)、ジクロロシラノ0゜0337モルをジクロロシ
ラ/導入管を通じて27分間で導入し、さらに反応温度
を77°0に保ちながら、7時間加熱反応させt−6こ
の反応混合物をそのまま実施例1と同様の反応条件でメ
タノール259gと反応させ、カラムクr、+ マドゲ
ラフィー(メルクネt、 Kieselgel 60a
rt、 7733 、展開溶媒、ンクロl\キサン・酢
酸エチル−6/1)でLit離精製を行ない3.19
!の生成物かt()らA]た。生成物の薄層りIJ7ト
ゲラフイーのRf値(メルク社Kiese1gel 6
0 F 254、展開溶媒 ンクロへNづ)/ll!1
酸エチルー4/′l)は0.57であった。
ン!1ら71j二牛成物の赤外線吸収スペクトルは17
20(7)−1に安、@ 香酸エステルのカルボニル吸
収、さらにI O90cm−’付近に5i−0−C(+
)強い吸収をホした。
またCI)CI 、中で測定した核磁只I(鳴ス・火り
トルは(δ値) 8.06 (m、4H) 、7.46
(nl。
6H) 、4.30 (t、4H) 、3.58 (s
、6H)、15〜2.2 (m、4H) 、0.5〜1
.0 (m、 4T−T )にングナルを示した。
元素分析は測定値C: 63.34、H: 6.92(
語 算 (1白 C: 6 3. 4 4 、
Tl : 6. 7 8 ) て あ −
) tこ 。
以ヒのテ−りJ: 11得られtコ化合物の構造は(C
,T(、C02(CIL) 3−128 i (OCT
い、−Cあると確認しt二。
く、発明の効果じ・
本発明の化合物は新規な化合物であり、新規な有機ケイ
素化合物の合成のための中間体として有用である。本発
明化合物を原料としt: srリノJ’lキサノは親油
性に優れておl)、化粗品、ワックス類の電気絶縁体部
、潤滑油、撥水剤、塗峯゛1、離型剤、消泡剤等の基材
として有用である。
まt:、シラノカップリング剤、水分架橋剤としても有
用である。【Ta. The structure of the compound obtained from the following I-take is (CTTI
I C(-)2 (CH2) :+ )2 S l (
0C1I: + 'I Confirm that it is 2 and press I. Example 2 A lot of his(:ooacetoxyp[copyl)dichlorosilane] and 48 g of isopropyl alcohol were reacted under the same reaction conditions as in Example 1, resulting in a boiling point of 153-154°C/3.
mHg product 9.4f was obtained (yield as high as 81). ? The line absorption subek I of the product of iJ is 17
Apply acetic acid nisful to 40 cm.
-C shows absorption. In addition, 1025n (5l near J)
It shows strong absorption of -0-C. In addition, the nuclear magnetic t (sound spectrum) measured in CDCl was (δ value) 3.9 to 4.4 (m, 6TICI
T,CO□CJLCILCILSi(ICJf(CH,
,)2),2. 0 6 (s. 6 H (-11=COzCH2-), 1.3-2.
] (rn, 4 ITClllCO, CfICI
(, CT(28i), 1.18 (d, +21
(S]CF((CIT+)2), 0.3~0
.. 8 (ITS, 411CIT, C02C+I,
CJj, CT (2S i), small amount of Gunar. Mass spectra were obtained using the CI method (chemical
zationmethod) using ammonia.
In two cases, a peak of M −+18-366 was measured! =
. One compound of J'l obtained from my son's take is (CIT,
C02(CIL), :125i(OCH(CI(i,
] At 2, - confirm. Example 3 His(3-acetoxyb-l]pyr)dichlorosilanoIOy and 7dylcelnorb5 were reacted under the same reaction conditions as in Example 1.
58g was reacted, boiling point 1 fi 5~170°C,
/ 10.742 f of one product of 1.2 T1 g was obtained. The obtained tKono4 parabolic Red Sun 1-ray absorption Subek] is 1
The carbonyl absorption of acetate ester is shown at 74 oz. Furthermore, strong absorption of S]-0-C is shown at +090/m'. - The CDC1, in which 1llll + determined nuclear magnetism JI
, the sound spectrum is (δ value) 4.03 (11,4TI)
, 3.88 (L, 4H) , 3.45 (1,lI
), 3.40 (s, 6II), 2.05 (s,
6H), 1.45-2. Signals are shown at OO (m. 411), 045-090 (m, 4■■). Mass spectrum is Ml-+18 by CI method (ammonia)
= 398 peaks were measured. The compound obtained from the above data is cCH,Co□(Cl+]2S](0C
Confirm that T-T2 CH20CtT.Example 4 Stirrer, drop Fr1. -1, Wensheng Ha 1? 11)? ,−
200d (D Hiss (:3-A I) in the Kermis reactor
! Tokinopu I-1 Building) Nokeroro 7.9715g, 1-
Richo-f no 1 a ζ, 12y1 Henose-100z (I 1
Add 10'('KJ 100% reaction at, t, without stirring, terl-futamer 88]) over 10 minutes. Return,
The mixture was further stirred for 1 hour and then carbonized for 6 hours. After reaction, l-I
After filtering the I-r-f amine hydrochloride for 7 hours, the reaction solvent was distilled off, and the reaction mixture was added to a 50 ml [11] If-7 reactor, and 5 ml of THF was added. Nipotassium tert-
Butoand (90% pure, 1,53 y) was heated to room temperature [
After dropping TITF with ζ for 10 hours, force → l・ri "171-graph(r(ieselgel)
60 art, 7733, developing solvent: acid-resistant ethylchlorhexane=■/3) to isolate product 1.591. The infrared absorption spectrum of the first product obtained is +74:1
Add the carbonyl absorption of acetate ester to m. Furthermore, 050 rys-' shows strong absorption of 5i-(1-C. Also, the t: nuclear magnetic resonance spectrum measured in CDCl is (δ value) 4.03 (t, 4H), 2 .06 (
s. 6H), 1.3-2.0 (m, 4H), 1.31'
(S. 18H), signals are shown at 0.4-0.9 (m, 4H). The mass spectrum is M when ammonia is used by the CI method.
+ l 8 = 394 peaks were measured. The compound obtained from the above data is [CH3Co2(CH,)2Si rOc(cH, +
)J], confirm that it is +. Example 5 Under the same reaction conditions as in Example 1, 5.873 y of his(3-butyloquinopropyl)dichlorosilane and 1.
] 58 y to a boiling point of 150-154℃/
0.49 mHg product 4.097 f'i-obtained
child. The infrared absorption spectrum of the obtained cow parallax is 1737
Absorption of carbonyl of butyrate ester in m-', and further I
Strong absorption of 5i-0-C was observed near O80nx'. Also measured in CI) C13, the sound spectrum was (δ value) 4. (12(t, 4T() , 3.54
(s. 6IT), 2.27 (L, 4T(), 1.3~2
.. 0 (m. 8H), 0.5-1. .. 1 (m, 10H) shows a signal. The mass spectrum was obtained using the Cr method <Fummonia> M118
= 36 (the peak of 1 was measured). The structure of the compound obtained from the following data is CCITI
C)L CFL C(% (CH2) 1:' 2 S
l (0CTT:l) Confirm that it is 2. Example 6 Into a reaction vessel for the argon purging method, equipped with a cyclolon run inlet pipe, an acetono-dry ice cooler, a rotor, and a temperature gauge 1, an ionobanol solution of allyl benzoate 10.932 and chloroplatinic acid (a %) 1112111
0.0337 mol of dichlorosilano was introduced in 27 minutes through the dichlorosilano/introduction tube, while maintaining the reaction temperature at 77°C to 88°C, while heating and stirring. The reaction mixture was heated for 7 hours and reacted with 259 g of methanol under the same reaction conditions as in Example 1.
rt, 7733, Lit separation and purification was performed using a developing solvent of 3.19
! The product of is t() from A]. Rf value of thin layer of product IJ7 Togelafy (Merck Kiesel Gel 6
0 F 254, developing solvent Nzu)/ll! 1
Ethyl acid (4/'l) was 0.57. hmm! 171j The infrared absorption spectrum of the adult cow is 17
At 20(7)-1, carbonyl absorption of folic acid ester occurs, and furthermore, 5i-0-C(+
) Has strong absorption. CI) CI, the nuclear magnetic field I (Narusu/Fire Tor) measured in CI (δ value) 8.06 (m, 4H), 7.46
(nl. 6H), 4.30 (t, 4H), 3.58 (s
, 6H), 15-2.2 (m, 4H), 0.5-1
.. 0 (m, 4T-T). Elemental analysis measured values C: 63.34, H: 6.92 (
Word arithmetic (1 white C: 6 3. 4 4,
Tl: 6. 7 8) Tea -
) tko. The structure of the compound obtained in 11 is (C
,T(,C02(CIL) 3-128 i(OCT
Yes, I confirmed that there was -C. Effects of the Invention The compounds of the present invention are novel compounds and are useful as intermediates for the synthesis of novel organosilicon compounds. Using the compound of the present invention as a raw material: SR Reno J'l It is useful as a base material for antifoaming agents, etc. It is also useful as a silano coupling agent and a water crosslinking agent.
第1図および第2図は本発明化合物であるヒス(3−ア
七 ヒ キンプロピ+l・)長メ トキ ンンランの
赤夕1線吸収スヘクl−Jl/ オヨヒ’tl核磁気其
鳴スペクI・ルのチへ・−1・をそ第1ぞれ示す。
特許出願人 東 し 株 式 会 社
手続補正書())式)
1.事件の表示
昭和60年特許頼第182545号
2、発明の名称
ビス(3−アシロキシプロピル)シアル]キシシラン3
、補正をする者
事例との関係 特許出願人
〒103
イ1所 東京都中央区]]本横室町2丁目2番地4、
補正命令の日付
昭和60升11月260(発送[1)
7、補正の内容
図面の第1図および第2図を別紙のとおり補正する。Figures 1 and 2 show the Red Sun 1-ray absorption spectra of the compound of the present invention, His(3-A7Hkinpropy+l), nuclear magnetic resonance spectra. -1 is shown in the first column. Patent Applicant Toshi Co., Ltd. Written Amendment to Procedures ()) 1. Case description 1985 Patent Request No. 182545 2 Name of invention Bis(3-acyloxypropyl)sial]xysilane 3
, Relationship with the case of the person making the amendment Patent applicant address: 103 I1 Chuo-ku, Tokyo]] Honyokomuromachi 2-2-4,
Date of amendment order: November 260, 1985 (Shipping [1)] 7. Contents of amendment Figures 1 and 2 of the drawings will be amended as shown in the attached sheet.
Claims (1)
OR^1)_2〔式中、Rは水素原子又は炭素原子数1
〜20個のアルキル基もしくはアリール基、R^1は炭
素原子数1〜5のアルキル基又はアルコキシアルキル基
を示す〕で示されるビス(3−アシロキシプロピル)ジ
アルコキシシラン。[Claims] The following general formula [RCO_2(CH_2)_3]_2Si(
OR^1)_2 [In the formula, R is a hydrogen atom or 1 carbon atom
-20 alkyl or aryl groups, R^1 represents an alkyl or alkoxyalkyl group having 1 to 5 carbon atoms] bis(3-acyloxypropyl)dialkoxysilane.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP60182545A JPS6242993A (en) | 1985-08-20 | 1985-08-20 | Bis(3-acyloxypropyl)dialkoxysilane |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP60182545A JPS6242993A (en) | 1985-08-20 | 1985-08-20 | Bis(3-acyloxypropyl)dialkoxysilane |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS6242993A true JPS6242993A (en) | 1987-02-24 |
Family
ID=16120158
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP60182545A Pending JPS6242993A (en) | 1985-08-20 | 1985-08-20 | Bis(3-acyloxypropyl)dialkoxysilane |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6242993A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017183347A1 (en) * | 2016-04-19 | 2017-10-26 | 信越化学工業株式会社 | Novel organosilicon compound and method for producing same |
-
1985
- 1985-08-20 JP JP60182545A patent/JPS6242993A/en active Pending
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017183347A1 (en) * | 2016-04-19 | 2017-10-26 | 信越化学工業株式会社 | Novel organosilicon compound and method for producing same |
CN108884116A (en) * | 2016-04-19 | 2018-11-23 | 信越化学工业株式会社 | Novel organo-silicon compound and its manufacturing method |
JPWO2017183347A1 (en) * | 2016-04-19 | 2019-02-14 | 信越化学工業株式会社 | Novel organosilicon compound and method for producing the same |
US10544170B2 (en) | 2016-04-19 | 2020-01-28 | Shin-Etsu Chemical Co., Ltd. | Organosilicon compound and method for producing same |
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