JPS6138197B2 - - Google Patents
Info
- Publication number
- JPS6138197B2 JPS6138197B2 JP53122801A JP12280178A JPS6138197B2 JP S6138197 B2 JPS6138197 B2 JP S6138197B2 JP 53122801 A JP53122801 A JP 53122801A JP 12280178 A JP12280178 A JP 12280178A JP S6138197 B2 JPS6138197 B2 JP S6138197B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- reaction
- organic
- present
- general formula
- 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.)
- Expired
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- -1 organosilane compounds Chemical class 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 12
- 229910000077 silane Inorganic materials 0.000 description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000006087 Silane Coupling Agent Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000011147 inorganic material Substances 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 239000011256 inorganic filler Substances 0.000 description 4
- 229910003475 inorganic filler Inorganic materials 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000010425 asbestos Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 229910052895 riebeckite Inorganic materials 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- RDOHPVPONNHSPH-UHFFFAOYSA-N octa-2,7-dienyl acetate Chemical compound CC(=O)OCC=CCCCC=C RDOHPVPONNHSPH-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- QPINXQCQOKBINJ-UHFFFAOYSA-K potassium;platinum(2+);trichloride Chemical compound [Cl-].[Cl-].[Cl-].[K+].[Pt+2] QPINXQCQOKBINJ-UHFFFAOYSA-K 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
本発明は有機シラン化合物に関する。
詳しくは、シランカツプリング剤等に有用な、
新規有機シラン化合物に関する。
シランカツプリング剤は、無機質と反応する置
換基と有機質と反応する置換基とを併せ有する有
機シラン化合物である。ガラス繊維、石綿などの
無機質の表面をシランカツプリング剤で処理する
ことにより、無機質と有機質とからなる複合材料
を製造する際、無機質と有機質の接着性および混
合性（相溶性）を改良し、複合材料の強度を向上
させることができる。
本発明者らは無機質と有機質に良好な接着性お
よび相溶性を付与するシランカツプリング剤につ
き検討した結果、特定構造の新規な有機シラン化
合物を見出し、本発明に到達した。
すなわち、本発明の目的は、シランカツプリン
グ剤として有用な、新規有機シラン化合物を提供
することであり、この目的は、一般式
R1COOCH2―R3―（CH2）5Si（OR2）3 ……（）
（ただし、R1は炭素数１〜10のアルキル基、
R2は炭素数１〜10のアルキル基またはアルコキ
シアルキル基、およびR3はエチレン基またはビ
ニレン基を示す）で表わされる有機シラン化合物
によつて達成される。
次に、本発明を詳細に説明する。
本発明の有機シラン化合物は、一般式
R1COOCH2―R3―（CH2）5Si（OR2）3で表わされ
る。
ここで、R1はメチル基、エチル基、プロピル
基、イソプロピル基、ブチル基、イソブチル基な
どの炭素数１〜10のアルキル基であり、R2は、
上記と同様の炭素数１〜10のアルキル基、また
は、２―メトキシエチル基、２―エトキシエチル
基、３―メトキシプロピル基、４―メトキシブチ
ル基などの炭素数１〜10のアルコキシアルキル基
である。
そして、R3はエチレン基またはビニレン基で
ある。
次に、上記有機シラン化合物の製造法について
説明する。
前記一般式（）においてR3がビニレン基で
ある化合物すなわち、R1COOCH2CH＝CH
（CH2）5Si（OR2）3
（ただし、R1およびR2は前記に同じ）を製造
するには、まず、一般式R1COOHで表わされる
カルボン酸とブタジエンとをパラジウム触媒の存
在下に反応させて、アシルオキシオクタジエンを
得る。
この反応において、ブタジエンの使用量は、用
いるカルボン酸に対して通常0.5〜20倍モル、好
ましくは1.0〜10倍モルの範囲から選ばれる。触
媒としては例えば酢酸パラジウム、パラジウムア
セチルアセトネート、チトラキストリフエニルホ
スフインパラジウム、ビストリフエニルホスフイ
ン酢酸パラジウム等が用いられる。
これらの触媒の使用量は、用いるカルボン酸に
対して１×10-4〜１×10-1倍モルが適当である。
反応温度は50〜130℃の範囲から選ばれる。
次いで、得られたアシルオキシオクタジエン
と、一般式（R2O）3SiH（ただし、R2は前記と同
じ）で表わされるトリアルコキシシランとを反応
させることにより、本発明の有機シラン化合物
R1COOCH2CH＝CH（CH2）5Si（OR2）3が得られ
る。
この反応において、トリアルコキシシランの使
用量は、アシルオキシオクタジエンに対して、通
常0.1〜20倍モル、好ましくは0.5〜10倍モルの範
囲から選ばれる。
触媒としては、例えば、塩化白金酸、塩化白金
属カリウム、ビストリフエニルホスフインジクロ
ロ白金、白金黒、または、白金をアスベスト、活
性炭、アルミナなどの担体上に分散させた白金触
媒が好適に用いられる。これらの触媒の使用量
は、アルコキシシランに対して１×10-6〜１×
10-2倍モルが適当である。
反応温度は20〜150℃の範囲から適宜選ばれ
る。
反応は無溶媒でも行なうことができるが、ｎ―
ヘプタン、ｎ―ヘキサンのような脂肪族炭化水
素、ベンゼン、トルエンのような芳香族炭化水素
などの溶媒中で行なつててもよい。
前記一般式（）でR3がエチレン基である化
合物、すなわち、R1COO（CH2）8Si（OR2）3は、
上記方法により得られたシラン化合物、
R1COOCH2CH＝CH（CH2）5Si（OR2）3を水添す
ることにより得られる。
水添触媒としては、ニツケル、コバルト、クロ
ム、銅、パラジウム、白金、ロジウム、オスミウ
ム、ルテニウム、レニウムなどの金属触媒が用い
られる。これらの金属触媒は、金属粉末または溶
媒に対して可溶性の塩、例えば、硫酸塩、リン酸
塩として用いてもよく、あるいはシリカ、アルミ
ナ、活性炭、ケイソウ土などの担体に担持させて
もよい。
触媒の使用量は、原料シランに対して、金属量
で、１×10-6〜１×10-2倍モルの範囲が適当であ
る。
反応は無溶媒でも行なうことができるが、ｎ―
ヘプタン、ｎ―ヘキサンのような脂肪族炭化水
素、ベンゼン、トルエンのような芳香族炭化水
素、もしくは前記一般式（）中のR2と同一の
アルキル基を有するアルコールなどの溶媒中で行
なつてもよい。
反応温度は20〜150℃、水素圧は１〜100Kg／cm2
の範囲から適宜選ばれる。
このようにして得られる有機シラン化合物はシ
ランカツプリング剤として有用である。
本発明の有機シラン化合物をシランカツプリン
グ剤として用いる方法の１例について説明する。
ガラズ繊維または石綿などの無機充填剤とこれ
に対して0.001〜１重量％の割合で、本発明の有
機シラン化合物とを混合し、無機充填剤の表面を
処理する。このとき、有機シラン化合物は水また
は有機溶媒で希釈して用いてもよい。処理後、無
機充填剤とポリエチレン、ポリプロピレンなどの
ポリオレフイン樹脂あるいは、飽和もししくは不
飽和ポリエステル樹脂等の有機質材料とを溶融混
合する。無機質充填材の使用量は有機質材料に対
して５〜60重量％の範囲が適当である。
溶融混合は、通常、混練機、押出機等を用いて
行なわれる。混合物は、ペレツト化したのち、成
形機により所望の形状の成形物とする。
本発明のシラン化合物をシランカツプリング剤
として用いることにより、機械的強度、耐熱性お
よび耐候性の優れた、有機質材料と無機質材料と
からなる複合材料を得ることができる。
次に本発明を実施例により具体的に説明する
が、本発明はその要旨を超えない限り以下の実施
例に限定されるものではない。
実施例 １
還流冷却器を備えた100mlフラスコに１―アセ
トキシ―2.7―オクタジエン3.36ｇ（20mmol）、
トリメトキシシラン2.42ｇ（19.8mmol）および
塩化白金酸のイソプロパノール溶液0.01ml（白金
として２×10-6mmol）を加え、撹拌しながら50
〜60℃で２時間、さらに90〜100℃で２時間反応
させた。
反応終了後、未反応物を追い出したのち、沸点
145℃／５mmHgの１―アセトキシ―７―トリメト
キシシリル―２―オクテン4.88ｇ（収率85％）を
得た。なお、得られた反応生成物の元素分析値、
NMRスペクトル値、IRスペクトル値を以下に示
す。
元素分析値： Ｃ Ｈ
計算値（％） 53.76 9.02
実験値（％） 53.79 9.03
NMRスペクトル δ値（ppm）
0.5（ｔ，2H，―CH2―Si）
1.23〜1.38（ｍ，6H，―CH2―）
1.95（ｓ，3H，
The present invention relates to organosilane compounds. For details, please refer to silane coupling agents, etc.
Regarding new organosilane compounds. A silane coupling agent is an organic silane compound having both a substituent that reacts with inorganic substances and a substituent that reacts with organic substances. By treating the surface of inorganic materials such as glass fibers and asbestos with a silane coupling agent, it is possible to improve the adhesion and mixing (compatibility) of inorganic and organic materials when manufacturing composite materials consisting of inorganic and organic materials. The strength of composite materials can be improved. The present inventors investigated a silane coupling agent that provides good adhesion and compatibility between inorganic and organic materials, and as a result discovered a novel organic silane compound with a specific structure and arrived at the present invention. That is, an object of the present invention is to provide a novel organosilane compound useful as a silane coupling agent, and this object has the general formula R 1 COOCH 2 --R 3 --(CH 2 ) 5 Si(OR 2 ) 3 ... () (However, R 1 is an alkyl group having 1 to 10 carbon atoms,
R 2 is an alkyl group or alkoxyalkyl group having 1 to 10 carbon atoms, and R 3 is an ethylene group or a vinylene group. Next, the present invention will be explained in detail. The organic silane compound of the present invention is represented by the general formula R 1 COOCH 2 —R 3 —(CH 2 ) 5 Si(OR 2 ) 3 . Here, R 1 is an alkyl group having 1 to 10 carbon atoms such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, and R 2 is
An alkyl group having 1 to 10 carbon atoms similar to the above, or an alkoxyalkyl group having 1 to 10 carbon atoms such as a 2-methoxyethyl group, 2-ethoxyethyl group, 3-methoxypropyl group, or 4-methoxybutyl group. be. And R 3 is an ethylene group or a vinylene group. Next, a method for producing the above organic silane compound will be explained. A compound in which R 3 is a vinylene group in the general formula (), that is, R 1 COOCH 2 CH=CH
To produce (CH 2 ) 5 Si(OR 2 ) 3 (where R 1 and R 2 are the same as above), first, a carboxylic acid represented by the general formula R 1 COOH and butadiene are combined in the presence of a palladium catalyst. The following reaction is performed to obtain acyloxyoctadiene. In this reaction, the amount of butadiene used is usually selected from the range of 0.5 to 20 times the mole, preferably 1.0 to 10 times the amount of the carboxylic acid used. As the catalyst, for example, palladium acetate, palladium acetylacetonate, thitrakistriphenylphosphine palladium, bistriphenylphosphine palladium acetate, etc. are used. The appropriate amount of these catalysts to be used is 1×10 −4 to 1×10 −1 times the amount of the carboxylic acid used. The reaction temperature is selected from the range of 50 to 130°C. Next, the obtained acyloxyoctadiene is reacted with a trialkoxysilane represented by the general formula (R 2 O) 3 SiH (where R 2 is the same as above) to produce the organosilane compound of the present invention.
R 1 COOCH 2 CH=CH(CH 2 ) 5 Si(OR 2 ) 3 is obtained. In this reaction, the amount of trialkoxysilane to be used is usually selected from the range of 0.1 to 20 times the mole, preferably 0.5 to 10 times the mole relative to the acyloxyoctadiene. As the catalyst, for example, chloroplatinic acid, platinum potassium chloride, bistriphenylphosphine dichloroplatinum, platinum black, or a platinum catalyst prepared by dispersing platinum on a carrier such as asbestos, activated carbon, or alumina is preferably used. . The amount of these catalysts used is 1×10 -6 to 1× relative to the alkoxysilane.
10 −2 times the molar amount is appropriate. The reaction temperature is appropriately selected from the range of 20 to 150°C. The reaction can be carried out without solvent, but n-
The reaction may be carried out in a solvent such as an aliphatic hydrocarbon such as heptane or n-hexane, or an aromatic hydrocarbon such as benzene or toluene. The compound in which R 3 is an ethylene group in the general formula (), that is, R 1 COO(CH 2 ) 8 Si(OR 2 ) 3 is,
The silane compound obtained by the above method is obtained by hydrogenating R 1 COOCH 2 CH=CH(CH 2 ) 5 Si(OR 2 ) 3 . As the hydrogenation catalyst, metal catalysts such as nickel, cobalt, chromium, copper, palladium, platinum, rhodium, osmium, ruthenium, and rhenium are used. These metal catalysts may be used as metal powders or salts soluble in solvents, such as sulfates and phosphates, or may be supported on carriers such as silica, alumina, activated carbon, diatomaceous earth, and the like. The appropriate amount of the catalyst to be used is 1×10 −6 to 1×10 −2 times the amount of metal based on the raw material silane. The reaction can be carried out without solvent, but n-
It is carried out in a solvent such as an aliphatic hydrocarbon such as heptane or n-hexane, an aromatic hydrocarbon such as benzene or toluene, or an alcohol having the same alkyl group as R 2 in the above general formula (). Good too. Reaction temperature is 20~150℃, hydrogen pressure is 1~100Kg/ cm2
Appropriately selected from the range. The organic silane compound thus obtained is useful as a silane coupling agent. An example of a method of using the organic silane compound of the present invention as a silane coupling agent will be described. An inorganic filler such as glass fiber or asbestos is mixed with the organic silane compound of the present invention in a proportion of 0.001 to 1% by weight, and the surface of the inorganic filler is treated. At this time, the organic silane compound may be diluted with water or an organic solvent before use. After the treatment, the inorganic filler and a polyolefin resin such as polyethylene or polypropylene or an organic material such as a saturated or unsaturated polyester resin are melt-mixed. The amount of inorganic filler used is suitably in the range of 5 to 60% by weight based on the organic material. Melt mixing is usually performed using a kneader, an extruder, or the like. After the mixture is pelletized, it is molded into a desired shape using a molding machine. By using the silane compound of the present invention as a silane coupling agent, a composite material made of an organic material and an inorganic material and having excellent mechanical strength, heat resistance, and weather resistance can be obtained. EXAMPLES Next, the present invention will be specifically explained with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof. Example 1 3.36 g (20 mmol) of 1-acetoxy-2.7-octadiene was added to a 100 ml flask equipped with a reflux condenser.
Add 2.42 g (19.8 mmol) of trimethoxysilane and 0.01 ml of isopropanol solution of chloroplatinic acid (2 x 10 -6 mmol as platinum), and add 50 g (19.8 mmol) of trimethoxysilane while stirring.
The reaction was carried out at ~60°C for 2 hours and then at 90-100°C for 2 hours. After the reaction is complete and unreacted substances are expelled, the boiling point is
4.88 g (yield: 85%) of 1-acetoxy-7-trimethoxysilyl-2-octene was obtained at 145° C./5 mmHg. In addition, the elemental analysis value of the obtained reaction product,
The NMR spectrum values and IR spectrum values are shown below. Elemental analysis values: C H Calculated value (%) 53.76 9.02 Experimental value (%) 53.79 9.03 NMR spectrum δ value (ppm) 0.5 (t, 2H, -CH 2 -Si) 1.23 - 1.38 (m, 6H, -CH 2 --) 1.95(s, 3H,
【式】） 2.05（ｄ，2H，―CH2―Ｃ＝Ｃ―） 3.43（ｓ，9H，―Ｏ―CH3） 4.38（ｄ，2H，[Formula]) 2.05 (d, 2H, -CH 2 -C=C-) 3.43 (s, 9H, -O-CH 3 ) 4.38 (d, 2H,
【式】）
5.5〜5.6（ｍ，2H，―CH＝CH―
IRスペクトル（cm-1）
2920、2840、1740、1460、1390、1375、1240、
1200、1090、1035、975、820、795
実施例 ２
しんとう式ガラス製気密容器（マーゲン）に１
―アセトキシ―７―トリメトキシシリル―２―オ
クテン13.66ｇ（47mmol）、メタノール50mlおよ
びパラジウム触媒（担体：活性炭担持体：５重量
％）200mgを仕込み、常圧で水素を導入して室温
でしんとうしながら１時間反応させた。反応終了
後、触媒を分離し、次いで溶媒および未反応物を
追い出したのち、沸点137℃／４mmHgの１―アセ
トキシ―７―トリメトキシシリル―ｎ―オクタン
11.76ｇ（収率85.7％）を得た。
なお、得られた反応生成物の屈折率、元素分析
値、NMRスペクトル値、IRスペクトル値を以下
に示す。
屈折率
ｎ２１ Ｄ＝1.4243
元素分析値 Ｃ Ｈ
計算値（％） 53.39 9.65
実験値（％） 53.36 9.69
NMRスペクトル δ値（ppm）
0.41〜0.58（ｔ，2H，―CH2―Si）
1.28〜1.40（ｍ，12H，―CH2―）
1.94（ｓ，3H，[Formula]) 5.5-5.6 (m, 2H, -CH=CH- IR spectrum (cm -1 ) 2920, 2840, 1740, 1460, 1390, 1375, 1240,
1200, 1090, 1035, 975, 820, 795 Example 2 1 in an airtight glass container (Magen)
13.66 g (47 mmol) of -acetoxy-7-trimethoxysilyl-2-octene, 50 ml of methanol, and 200 mg of palladium catalyst (carrier: activated carbon support: 5% by weight) were charged, hydrogen was introduced at normal pressure, and the mixture was stirred at room temperature. The reaction was allowed to proceed for 1 hour. After the reaction is completed, the catalyst is separated, and the solvent and unreacted substances are expelled.
11.76g (yield 85.7%) was obtained. The refractive index, elemental analysis value, NMR spectrum value, and IR spectrum value of the obtained reaction product are shown below. Refractive index n 21 D = 1.4243 Elemental analysis value C H Calculated value (%) 53.39 9.65 Experimental value (%) 53.36 9.69 NMR spectrum δ value (ppm) 0.41 to 0.58 (t, 2H, -CH 2 -Si) 1.28 to 1.40 (m, 12H, -CH 2 -) 1.94 (s, 3H,
【式】） 3.41（ｓ，9H，―Ｏ―CH3） 3.91（ｔ，2H，[Formula]) 3.41 (s, 9H, -O-CH 3 ) 3.91 (t, 2H,
【式】）
IRスペクトル（cm-1）
2920、2840、1740、1470、1395、1380、1240、
1200、1090、1050、820、795[Formula]) IR spectrum (cm -1 ) 2920, 2840, 1740, 1470, 1395, 1380, 1240,
1200, 1090, 1050, 820, 795
Claims (1)
……（） （ただし、R1は炭素数１〜10のアルキル基、
R2は炭素数１〜10のアルキル基またはアルコキ
シアルキル基およびR3はエチレン基またはビニ
レン基を示す）で表わされる有機シラン化合物。[Claims] 1 General formula R 1 COOCH 2 —R 3 —(CH 2 ) 5 Si(OR 2 ) 3
...() (However, R 1 is an alkyl group having 1 to 10 carbon atoms,
R 2 is an alkyl group or alkoxyalkyl group having 1 to 10 carbon atoms, and R 3 is an ethylene group or a vinylene group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12280178A JPS5549387A (en) | 1978-10-05 | 1978-10-05 | Organo-silane compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12280178A JPS5549387A (en) | 1978-10-05 | 1978-10-05 | Organo-silane compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5549387A JPS5549387A (en) | 1980-04-09 |
| JPS6138197B2 true JPS6138197B2 (en) | 1986-08-28 |
Family
ID=14844966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12280178A Granted JPS5549387A (en) | 1978-10-05 | 1978-10-05 | Organo-silane compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5549387A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11003227B2 (en) | 2015-06-03 | 2021-05-11 | Mitsubishi Electric Corporation | Liquid-type cooling apparatus and manufacturing method for heat radiation fin in liquid-type cooling apparatus |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6087499B2 (en) * | 2011-10-18 | 2017-03-01 | 信越化学工業株式会社 | Thermally conductive silicone composition |
-
1978
- 1978-10-05 JP JP12280178A patent/JPS5549387A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11003227B2 (en) | 2015-06-03 | 2021-05-11 | Mitsubishi Electric Corporation | Liquid-type cooling apparatus and manufacturing method for heat radiation fin in liquid-type cooling apparatus |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5549387A (en) | 1980-04-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR102201058B1 (en) | Organoaminosilanes and methods for making same | |
| EP0403706A2 (en) | Process for preparing amino-propyl silanes | |
| CN102532186B (en) | Method for preparing hydroxyimino organosilicon compounds | |
| JP5115729B2 (en) | Organosilicon compound containing acetoacetate group protected with trialkylsilyl group and process for producing the same | |
| JPS6143692A (en) | Reactive antioxidant compound, manufacture and stabilized polymer composition | |
| JP2005509683A (en) | Method for producing bis (silylorgano) amine | |
| CA2043383C (en) | Sterically hindered aminohydrocarbyl silanes and process of preparation | |
| CN1085558A (en) | The novel rhodium-containing catalysts selective of synthesizing epoxy (gathering) siloxanyl monomers and polymkeric substance | |
| JPS61277692A (en) | Phenylene group-containing organosilane and its production | |
| JPS6138197B2 (en) | ||
| JPH01132591A (en) | Dimerized vinylcycloheptyl group-containing silicon compound and its production | |
| EP1149837A2 (en) | Organosilicon compounds | |
| JPS59157089A (en) | Manufacture of bera-phenylethylchlorosilane | |
| JP2010013653A (en) | Organic silicon resin having alcoholic hydroxy group and its manufacturing method | |
| JPH0786117B2 (en) | Alkoxy silane | |
| JP2002193976A (en) | Production method of n-substituted-3-silylpropylamine and its derivative | |
| JP2003082102A (en) | Process for manufacturing organooxy group- or hydroxy group-containing siloxane | |
| JP3622002B2 (en) | Method for producing formoxysilane | |
| JPH10120689A (en) | Production of silicon-based compound and silicon-based polymer | |
| JPH0459783A (en) | Fluorine-containing organic silicon compound | |
| JP4081572B2 (en) | Method for silylating a compound having a hydroxyl group | |
| US5113000A (en) | Organosilicon compound and acryl compound | |
| JPH11158187A (en) | Production of compound containing silicon and polymer-containing silicon | |
| JPH085903B2 (en) | Epoxy group-containing alkoxysiloxane and method for producing the same | |
| JPH0334988A (en) | Siloxane compound containing alkoxy group |