JPS6138195B2 - - Google Patents
Info
- Publication number
- JPS6138195B2 JPS6138195B2 JP763680A JP763680A JPS6138195B2 JP S6138195 B2 JPS6138195 B2 JP S6138195B2 JP 763680 A JP763680 A JP 763680A JP 763680 A JP763680 A JP 763680A JP S6138195 B2 JPS6138195 B2 JP S6138195B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- ethylacetamido
- silane
- divinyl
- dimethyl
- 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
- -1 1,3-dimethyl-1,3-divinyl-1, 3-di-(N-ethylacetamido)disiloxane Chemical compound 0.000 claims description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical compound CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IMPVGWPSUORTEQ-UHFFFAOYSA-N N-[[acetyl(ethyl)amino]-prop-1-enylsilyl]-N-ethylacetamide Chemical compound CC=C[SiH](N(C(C)=O)CC)N(C(C)=O)CC IMPVGWPSUORTEQ-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000003961 organosilicon compounds Chemical class 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 125000005372 silanol group Chemical group 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- QUEXZWPCJMZORR-UHFFFAOYSA-N N-ethyl-N-silylacetamide Chemical compound C(C)N(C(C)=O)[SiH3] QUEXZWPCJMZORR-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- QNXUEHHVVZBQHD-UHFFFAOYSA-N chloro-(chloro-ethenyl-methylsilyl)oxy-ethenyl-methylsilane Chemical compound C=C[Si](Cl)(C)O[Si](C)(Cl)C=C QNXUEHHVVZBQHD-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- FLEZTVNVBFPJHL-UHFFFAOYSA-N dichloro(silyloxy)silane Chemical compound [SiH3]O[SiH](Cl)Cl FLEZTVNVBFPJHL-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- BPMXEJSBTONLLG-UHFFFAOYSA-N n-[[acetyl(methyl)amino]-prop-1-enylsilyl]-n-methylacetamide Chemical compound CC=C[SiH](N(C)C(C)=O)N(C)C(C)=O BPMXEJSBTONLLG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Description
【発明の詳細な説明】
この発明は新規化合物である１，３―ジメチル
−１，３―ジビニル―１，３―ジ―（Ｎ―エチル
アセトアミド）ジシロキサンに関する。DETAILED DESCRIPTION OF THE INVENTION This invention relates to a novel compound, 1,3-dimethyl-1,3-divinyl-1,3-di-(N-ethylacetamido)disiloxane.
けい素原子にアミド基が結合した有機けい素化
合物としては、たとえば米国特許第3488371号明
細書に下記のようなジアミドシランおよびジアミ
ドシロキサンが記載されている。 As organosilicon compounds in which an amide group is bonded to a silicon atom, the following diamidosilanes and diamidosiloxanes are described, for example, in US Pat. No. 3,488,371.
上記においてPhはフエニル基を示す。以下同様
また、米国特許第2836234号明細書には下記一
般式で示されるアミドシランが記載されている。 In the above, Ph represents a phenyl group. Similarly, US Pat. No. 2,836,234 describes an amidosilane represented by the following general formula.
式中R1はシクロヘキシル基、シクロヘキセニ
ル基、フエニル基、炭素数１〜18のアルケニル基
あるいはアルキル基、R2は水素原子、炭素数１
〜18のアルキル基あるいはアルケニル基、R3は
水素原子、シクロヘキシル基、シクロヘキセニル
基、フエニル基、炭素数１〜18のアルケニル基あ
るいはアルキル基、ｘは１〜４である。 In the formula, R 1 is a cyclohexyl group, a cyclohexenyl group, a phenyl group, an alkenyl group or an alkyl group having 1 to 18 carbon atoms, and R 2 is a hydrogen atom or a carbon number 1
-18 alkyl group or alkenyl group, R3 is a hydrogen atom, cyclohexyl group, cyclohexenyl group, phenyl group, alkenyl group or alkyl group having 1 to 18 carbon atoms, and x is 1 to 4.
さらに米国特許第3776934号明細書にはメチル
ビニル―ジ―（Ｎ―メチルアセトアミド）シラン
が記載されている。。 Additionally, US Pat. No. 3,776,934 describes methylvinyl-di-(N-methylacetamido)silane. .
こうした従来公知のアミド基含有有機けい素化
合物のうちでも、メチルビニル―ジ―（Ｎ―エチ
ルアセトアミド）シランは、多官能性アミノオキ
シシロキサン化合物と共に主剤としての両末端水
酸基封鎖ジオルガノポリシロキサンに配合するこ
とにより硬化性組成物を得ることができ、このメ
チルビニル―ジ―（Ｎ―エチルアセトアミド）シ
ランは両末端水酸基封鎖ジオルガノポリシロキサ
ンを連鎖的に高分子化（鎖長延長化）させる働き
を示す。 Among these conventionally known amide group-containing organosilicon compounds, methylvinyl-di-(N-ethylacetamido)silane is blended together with a polyfunctional aminooxysiloxane compound into a diorganopolysiloxane blocked at both hydroxyl ends as a base ingredient. By doing this, a curable composition can be obtained, and this methylvinyl-di-(N-ethylacetamido)silane functions to polymerize (lengthen the chain) the diorganopolysiloxane blocked with hydroxyl groups at both ends. shows.
しかしながら、この硬化性組成物は５℃以下に
冷却した場合、組成物中に結晶が生成するという
欠点があり、同時に垂れ防止性（ノンサグ性）が
悪くなる。これは該メチルビニル―ジ―（Ｎ―エ
チルアセトアミド）シランが水分あるいは両末端
水酸基封鎖ジオルガノポリシロキサンのシラノー
ル基と反応して副生するアミド化合物に起因して
いる。 However, this curable composition has the disadvantage that crystals form in the composition when it is cooled to 5° C. or lower, and at the same time, the anti-sagging properties (non-sag properties) deteriorate. This is due to the amide compound produced as a by-product when the methylvinyl-di-(N-ethylacetamido)silane reacts with moisture or the silanol groups of the diorganopolysiloxane endblocked with hydroxyl groups at both ends.
また、上記組成物においてメチルビニル―ジ―
（Ｎ―エチルアセトアミド）シランの代りにメチ
ルビニルージ―（Ｎ―メチルアセトアミド）シラ
ンを使用すると、充分な鎖長延長化効果が得られ
ず、硬化物はモジユラスが高いという欠点を有す
る。 Furthermore, in the above composition, methylvinyl di-
If methylvinyludi(N-methylacetamido)silane is used instead of (N-ethylacetamido)silane, a sufficient chain lengthening effect cannot be obtained, and the cured product has the disadvantage of high modulus.
本発明の新規化合物すなわち１，３―ジメチル
―１，３―ジビニル―１，３―ジ―（Ｎ―エチル
アセトアミド）ジシロキサンは、水分あるいはシ
ラノール基と反応しても結晶性のアミド化合物を
遊離せず、また前記のような組成物に応用した場
合、良好なノンサグ性を有し、しかもすぐれた反
応性を示し両末端水酸基封鎖ジオルガノポリシロ
キサンの鎖長延長化効果が大きいという特徴を有
するものである。 The novel compound of the present invention, 1,3-dimethyl-1,3-divinyl-1,3-di-(N-ethylacetamido)disiloxane, releases a crystalline amide compound even when it reacts with moisture or silanol groups. Moreover, when applied to the above-mentioned composition, it has the characteristics of having good non-sag properties, excellent reactivity, and a large chain lengthening effect of the diorganopolysiloxane blocked at both terminals with hydroxyl groups. It is something.
この新規化合物は、塩酸捕獲剤の存在下に、
１，３―ジメチル―１，３―ジビニル―１，３―
ジクロロジシロキサンとＮ―エチルアセトアミド
とを反応させることにより合成することができ
る。塩酸捕獲剤としてはピリジン、トリエチルア
ミン等の３級アミンが好ましく、反応温度は０〜
150℃とすればよい。 This new compound, in the presence of a hydrochloric acid scavenger,
1,3-dimethyl-1,3-divinyl-1,3-
It can be synthesized by reacting dichlorodisiloxane and N-ethylacetamide. As the hydrochloric acid scavenger, tertiary amines such as pyridine and triethylamine are preferable, and the reaction temperature is 0 to 0.
The temperature should be 150℃.
なお、上記反応は多量の塩酸塩が副生されるの
で、かくはんを容易にするためベンゼン、トルエ
ン、キシレン等の不活性溶媒を使用することが望
ましい。 In addition, since a large amount of hydrochloride is produced as a by-product in the above reaction, it is desirable to use an inert solvent such as benzene, toluene, or xylene to facilitate stirring.
つぎに具体的実施例をあげる。 Next, specific examples will be given.
実施例
反応フラスコにトルエン1000ｇ、１，３―ジメ
チル―１，３―ジビニル―１，３―ジクロロジシ
ロキサン125ｇ（0.55モル）を仕込み、トリエチ
ルアミン304ｇ（3.0モル）を添加したのちＮ―エ
チルアセトアミド113ｇ（1.3モル）を30分を要し
て滴下した。滴下することにより反応温度は25℃
から55℃まで上昇した。反応系内を60℃にして２
時間かくはんし反応させた。Example A reaction flask was charged with 1000 g of toluene and 125 g (0.55 mol) of 1,3-dimethyl-1,3-divinyl-1,3-dichlorodisiloxane, and after adding 304 g (3.0 mol) of triethylamine, 113 g of N-ethylacetamide was added. (1.3 mol) was added dropwise over 30 minutes. By dropping, the reaction temperature is 25℃
The temperature rose from 55℃ to 55℃. The temperature inside the reaction system was set to 60°C.
The mixture was stirred and reacted for a period of time.
その後トリエチルアミン塩酸塩をろ別し、ろ液
を減圧蒸留したところ、沸点125℃／３mmHgの液
状物が136ｇ得られた（収率75％）。 Thereafter, triethylamine hydrochloride was filtered off, and the filtrate was distilled under reduced pressure to obtain 136 g of a liquid substance with a boiling point of 125° C./3 mmHg (yield: 75%).
この生成物は常温で液体状のものであり、−30
℃下でも液状を保持していた。 This product is liquid at room temperature, −30
It remained liquid even at ℃.
元素分析： Ｃ Ｈ Ｎ 計算値（％） 51.17 8.58 8.52 分析値（％） 51.30 8.63 8.50 赤外線吸収スペクトル分析： 別紙図面のとおり。 Elemental analysis: C H N Calculated value (%) 51.17 8.58 8.52 Analysis value (%) 51.30 8.63 8.50 Infrared absorption spectrum analysis: As shown in the attached drawing.
25℃における屈折率：1.4670
上記結果から生成物は下記分子式の化合物であ
ることが確認された。 Refractive index at 25°C: 1.4670 From the above results, it was confirmed that the product was a compound having the following molecular formula.
１，３―ジメチル―１，３―ジビニル―１，３
―ジ―（Ｎ―エチルアセトアミド）ジシロキサ
ン 1,3-dimethyl-1,3-divinyl-1,3
-Di-(N-ethylacetamido)disiloxane
図面は実施例で得られた生成物の赤外線吸収ス
ペクトル分析の結果を示したものである。
The drawing shows the results of infrared absorption spectrum analysis of the products obtained in the examples.
Claims (1)
３―ジ―（Ｎ―エチルアセトアミド）ジシロキサ
ン1 1,3-dimethyl-1,3-divinyl-1,
3-di-(N-ethylacetamido)disiloxane
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP763680A JPS56104888A (en) | 1980-01-25 | 1980-01-25 | 1,3-dimethyl-1,3-divinyl-1,3-di- n-ethylacetamide disiloxane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP763680A JPS56104888A (en) | 1980-01-25 | 1980-01-25 | 1,3-dimethyl-1,3-divinyl-1,3-di- n-ethylacetamide disiloxane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56104888A JPS56104888A (en) | 1981-08-20 |
| JPS6138195B2 true JPS6138195B2 (en) | 1986-08-28 |
Family
ID=11671308
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP763680A Granted JPS56104888A (en) | 1980-01-25 | 1980-01-25 | 1,3-dimethyl-1,3-divinyl-1,3-di- n-ethylacetamide disiloxane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56104888A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0967021A (en) * | 1995-08-31 | 1997-03-11 | Japan Small Corp | Unloading equipment for bulk cargo |
-
1980
- 1980-01-25 JP JP763680A patent/JPS56104888A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0967021A (en) * | 1995-08-31 | 1997-03-11 | Japan Small Corp | Unloading equipment for bulk cargo |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56104888A (en) | 1981-08-20 |
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