JPH04252229A - Silicone compound and production thereof - Google Patents
Silicone compound and production thereofInfo
- Publication number
- JPH04252229A JPH04252229A JP905091A JP905091A JPH04252229A JP H04252229 A JPH04252229 A JP H04252229A JP 905091 A JP905091 A JP 905091A JP 905091 A JP905091 A JP 905091A JP H04252229 A JPH04252229 A JP H04252229A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- reaction
- silicone compound
- allyl acetate
- hydrosilicone
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 38
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 18
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 9
- 239000000126 substance Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 abstract description 16
- 239000002994 raw material Substances 0.000 abstract description 10
- 239000002253 acid Substances 0.000 abstract description 5
- 239000011248 coating agent Substances 0.000 abstract description 5
- 239000000203 mixture Substances 0.000 abstract description 5
- 238000000576 coating method Methods 0.000 abstract description 4
- 239000000565 sealant Substances 0.000 abstract description 4
- 239000000853 adhesive Substances 0.000 abstract description 2
- 230000001070 adhesive effect Effects 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000005370 alkoxysilyl group Chemical group 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 239000003973 paint Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 150000004687 hexahydrates Chemical class 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product 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
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- NZCRJKRKKOLAOJ-XRCRFVBUSA-N rifaximin Chemical compound OC1=C(C(O)=C2C)C3=C4N=C5C=C(C)C=CN5C4=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O NZCRJKRKKOLAOJ-XRCRFVBUSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 239000005028 tinplate Substances 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
Landscapes
- Silicon Polymers (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は、耐候性、耐熱性の優れ
た塗料、コーティング剤、シーリング剤、接着剤などの
原料として有用なシリコーン化合物及びその製法に関す
る。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a silicone compound useful as a raw material for paints, coating agents, sealants, adhesives, etc., which have excellent weather resistance and heat resistance, and a method for producing the same.
【０００２】0002
【従来の技術】分子末端あるいは側鎖にアルコキシシリ
ル基を有するビニル系重合体は公知である（特開昭５４
−３６３９５号公報、特開昭５４−４０８９３号公報、
特開昭５４−１２３１９２号公報）。ビニル系重合体の
末端あるいは側鎖に、アルコキシシリル基を導入するこ
とにより、ビニル系重合体の特徴である高光沢、耐候性
、耐変色性等のすぐれた特徴だけでなく、アルコキシシ
リル基による無機物に対する密着性の向上、さらに水分
特に大気中の水分による常温架橋で緻密な網状構造を形
成し、耐溶剤性、耐水性、耐熱性、高い硬度、耐候性の
すぐれた重合体になることなどが知られている。[Prior Art] Vinyl polymers having alkoxysilyl groups at the molecular terminals or side chains are known (Japanese Patent Laid-Open No. 54
-36395 publication, JP-A-54-40893 publication,
(Japanese Unexamined Patent Publication No. 54-123192). By introducing an alkoxysilyl group to the end or side chain of a vinyl polymer, it not only has the excellent characteristics of vinyl polymers such as high gloss, weather resistance, and discoloration resistance, but also the alkoxysilyl group. It improves adhesion to inorganic substances, and forms a dense network structure through room-temperature crosslinking with moisture, especially atmospheric moisture, resulting in polymers with excellent solvent resistance, water resistance, heat resistance, high hardness, and weather resistance. It has been known.
【０００３】0003
【発明が解決しようとする課題】しかしながら、最近建
築分野において屋外外装用として、さらに耐候性のすぐ
れた塗料原料が求められている。[Problems to be Solved by the Invention] However, recently there has been a demand for paint raw materials with even better weather resistance for outdoor exterior use in the architectural field.
【０００４】0004
【課題を解決するための手段】本発明者らは、下記化３
で示されるラダー型ヒドロシリコーン化合物と酢酸アリ
ルとを、ＶＩＩＩ族白金系の触媒下で反応させることに
より得られるシリコーン化合物は、塗膜性能、特に耐候
性がすぐれた硬化性組成物の原料として用いることがで
きることを見出し、本発明を完成した。[Means for solving the problem] The present inventors have developed the following formula 3:
The silicone compound obtained by reacting the ladder-type hydrosilicone compound represented by the formula with allyl acetate in the presence of a group VIII platinum-based catalyst is used as a raw material for a curable composition with excellent coating performance, particularly weather resistance. They discovered that it is possible to do this, and completed the present invention.
【０００５】[0005]
【化３】[Chemical formula 3]
【０００６】即ち、本発明は、下記化４で示されるシリ
コーン化合物、及び下記化５で表されるラダー型ヒドロ
シリコーン化合物と酢酸アリルとを白金系触媒の存在下
、５０〜１５０℃で反応させることを特徴とするシリコ
ーン化合物の製法である。That is, the present invention involves reacting a silicone compound represented by the following chemical formula 4, a ladder-type hydrosilicone compound represented by the following chemical formula 5, and allyl acetate at 50 to 150°C in the presence of a platinum catalyst. This is a method for producing a silicone compound characterized by the following.
【０００７】[0007]
【化４】[C4]
【０００８】[0008]
【化５】[C5]
【０００９】本発明のシリコーン化合物は、新規な物質
である。本発明のシリコーン化合物、アルコキシシリル
基を有するビニル系重合体、及び硬化促進触媒等を配合
した硬化性組成物は、硬化した塗膜の耐候性、耐熱性が
大巾に向上する。本発明のシリコーン化合物の製造に用
いられるヒドロシリコーン化合物は、トリクロロシラン
をジオキサン等の溶媒中で水を加えて加水分解したのち
、メタノール、エタノール等の低級アルコールを加えて
アルコキシ化することによって得られる。The silicone compound of the present invention is a new material. The curable composition containing the silicone compound of the present invention, a vinyl polymer having an alkoxysilyl group, a curing accelerating catalyst, etc. greatly improves the weather resistance and heat resistance of the cured coating film. The hydrosilicone compound used in the production of the silicone compound of the present invention is obtained by hydrolyzing trichlorosilane in a solvent such as dioxane by adding water, and then alkoxylating it by adding a lower alcohol such as methanol or ethanol. .
【００１０】本発明に用いられるラダー型ヒドロシリコ
ーン化合物を具体的に示すと下記化６の通りである。The ladder-type hydrosilicone compound used in the present invention is specifically shown in the following formula 6.
【００１１】[0011]
【化６】[C6]
【００１２】本発明のシリコーン化合物は、ラダー型ヒ
ドロシリコーン化合物のＳｉ−Ｈ基に酢酸アリルを付加
することにより得られるが、この反応において第ＶＩＩ
Ｉ族白金系触媒を必要とする。第ＶＩＩＩ族白金系触媒
としては、白金の単体、塩化白金酸、アルコール変性塩
化白金酸、塩化白金−オレフィン錯体、アルミナ、シリ
カ等の担体に固体白金を担持させたもの、ロジウム−オ
レフィン錯体など、コバルト、パラジウムおよびニッケ
ルから選ばれたＶＩＩＩ族の金属化合物が有効に使用さ
れる。触媒の使用量は通常反応物に対して、１〜１，０
００ｐｐｍの量が用いられる。The silicone compound of the present invention can be obtained by adding allyl acetate to the Si-H group of a ladder-type hydrosilicone compound, and in this reaction, VII
Requires Group I platinum catalyst. Group VIII platinum-based catalysts include simple platinum, chloroplatinic acid, alcohol-modified chloroplatinic acid, chlorinated platinum-olefin complexes, solid platinum supported on supports such as alumina and silica, and rhodium-olefin complexes. Group VIII metal compounds selected from cobalt, palladium and nickel are advantageously used. The amount of catalyst used is usually 1 to 1.0% based on the reactants.
An amount of 00 ppm is used.
【００１３】このヒドロシリル化反応は、５０〜１５０
℃の温度で反応時間は１〜５時間で達成される。反応温
度が５０℃以下の場合は反応速度が遅くなり実用的でな
い。また反応温度が１５０℃以上になると一部高分子量
物が生成したりゲル化反応が起るので好ましくない。本
発明において、ラダー型ヒドロシリコーン化合物と酢酸
アリルとを反応させるときのモル比は、目標とする反応
生成物により変わるが、通常、Ｓｉ−Ｈ基１モルに対し
て、酢酸アリルを０．１〜５．０モルの範囲が好ましい
。[0013] This hydrosilylation reaction
At a temperature of 0.degree. C., reaction times are achieved in 1 to 5 hours. If the reaction temperature is 50°C or less, the reaction rate becomes slow and it is not practical. Furthermore, if the reaction temperature exceeds 150° C., it is not preferable because some high molecular weight substances may be produced or a gelation reaction may occur. In the present invention, the molar ratio when the ladder-type hydrosilicone compound and allyl acetate are reacted varies depending on the target reaction product, but usually 0.1 allyl acetate is added to 1 mole of Si-H group. The range of 5.0 mol is preferred.
【００１４】本発明において、ラダー型ヒドロシリコー
ン化合物と酢酸アリルの反応で、溶媒を用いてもよい。
用いられる溶媒としては、ラダー型ヒドロシリコーン化
合物と酢酸アリルをともに溶解する溶媒が好ましい。通
常、トルエン、キシレン等の有機溶媒が用いられる。溶
媒を使用する場合は、反応に用いる原料１重量部に対し
て０．１〜１０重量部を用いることが好ましい。In the present invention, a solvent may be used in the reaction between the ladder-type hydrosilicone compound and allyl acetate. The solvent used is preferably a solvent that dissolves both the ladder-type hydrosilicone compound and allyl acetate. Usually, organic solvents such as toluene and xylene are used. When using a solvent, it is preferable to use 0.1 to 10 parts by weight per 1 part by weight of the raw material used for the reaction.
【００１５】本発明のシリコーン化合物は、大気中に暴
露されると、アルコキシシリル基が大気中の水分と反応
して、常温で網状組織を形成して硬化する。本発明のシ
リコーン化合物は、加水分解性シリル基を含有する他の
化合物と混合して硬化させることもできる。例えば、分
子末端あるいは側鎖にアルコキシシリル基を持つビニル
重合体と本発明のシリコーン化合物とを混合して、硬化
させることもできる。本発明のシリコーン化合物を硬化
させるにあたっては、硬化促進剤を使用することもでき
る。用いられる硬化促進剤としては有機スズ化合物、有
機チタン化合物、有機アルミニウム化合物、アミン類な
どやその他の酸性硬化促進剤及び塩基性硬化促進剤が有
効である。これらの硬化促進剤の添加量は、硬化させる
化合物に対して０．０１〜１０重量％使用するのが好ま
しい。When the silicone compound of the present invention is exposed to the atmosphere, the alkoxysilyl groups react with moisture in the atmosphere to form a network structure and harden at room temperature. The silicone compound of the present invention can also be cured by mixing with other compounds containing hydrolyzable silyl groups. For example, a vinyl polymer having an alkoxysilyl group at the molecular end or side chain and the silicone compound of the present invention can be mixed and cured. A curing accelerator can also be used in curing the silicone compound of the present invention. As the curing accelerator used, organic tin compounds, organic titanium compounds, organic aluminum compounds, amines, and other acidic curing accelerators and basic curing accelerators are effective. The amount of these curing accelerators added is preferably 0.01 to 10% by weight based on the compound to be cured.
【００１６】本発明のシリコーン化合物は、塗料、シー
リング剤、コーティング剤等の硬化性組成物の原料とし
て有用である。本発明のシリコーン化合物は、用途に応
じて、種々の充填剤、顔料等をブレンドすることが可能
である。充填剤、顔料としては、例えば各種シリカ類、
炭酸カルシウム、炭酸マグネシウム、酸化チタン、酸化
鉄、ガラス繊維等種々のものが使用可能である。The silicone compound of the present invention is useful as a raw material for curable compositions such as paints, sealants, and coating agents. The silicone compound of the present invention can be blended with various fillers, pigments, etc. depending on the application. Examples of fillers and pigments include various silicas,
Various materials such as calcium carbonate, magnesium carbonate, titanium oxide, iron oxide, and glass fiber can be used.
【００１７】[0017]
【実施例】以下、実施例により本発明を説明する。[Examples] The present invention will be explained below with reference to Examples.
【００１８】[0018]
【実施例１】温度計、攪拌用回転子、冷却管を取付けた
３００ｍｌの３口フラスコに、酢酸アリル３３．１ｇ（
０．３３モル）、キシレン４６ｇ、塩化白金酸６水塩１
７ｍｇを入れ、攪拌しながら温度を８０℃まで上げた。
次に下記化７に示す構造式のヒドロシリコーン化合物１
３．１ｇ（Ｓｉ−Ｈ基０．１４５モル）をフラスコ内へ
２０分かけて滴下した。滴下終了後８０℃でさらに５時
間反応した。反応終了後、反応液中の溶媒及び未反応の
酢酸アリルを真空蒸発で除去した。２５．９ｇの液状生
成物が得られた。生成物中の未反応のＳｉ−Ｈ基をアル
カリ分解法で測定した結果Ｓｉ−Ｈ基の反応率は８８％
であった。赤外吸収スペクトル及び １Ｈ−ＮＭＲによ
る解析の結果、生成物は原料のヒドロシリコーン化合物
のＳｉ−Ｈ基の８８％が化８に変換した化合物であるこ
とを確認した。[Example 1] 33.1 g of allyl acetate (
0.33 mol), xylene 46 g, chloroplatinic acid hexahydrate 1
7 mg was added, and the temperature was raised to 80°C while stirring. Next, hydrosilicone compound 1 having the structural formula shown in the following chemical formula 7
3.1 g (0.145 mol of Si-H group) was dropped into the flask over 20 minutes. After the dropwise addition was completed, the reaction was continued at 80°C for an additional 5 hours. After the reaction was completed, the solvent and unreacted allyl acetate in the reaction solution were removed by vacuum evaporation. 25.9 g of liquid product was obtained. As a result of measuring the unreacted Si-H groups in the product using an alkaline decomposition method, the reaction rate of Si-H groups was 88%.
Met. As a result of analysis by infrared absorption spectrum and 1H-NMR, it was confirmed that the product was a compound in which 88% of the Si-H groups of the hydrosilicone compound as a raw material were converted to Chemical Formula 8.
【００１９】[0019]
【化７】[C7]
【００２０】[0020]
【化８】[Chemical formula 8]
【００２１】[0021]
【実施例２】実施例１と同じ装置に酢酸アリル５０ｇ（
０．５０モル）、塩化白金酸６水塩の５％イソプロパノ
ール溶液０．２ｇ、トルエン７０ｇを入れ、攪拌しなが
ら温度を８０℃まで上げた。次に下記化９に示す構造式
を持つヒドロシリコーン化合物３０．５ｇ（Ｓｉ−Ｈ基
０．５０モル）をフラスコ内へ２０分間かけて滴下した
。滴下終了後８０℃で５時間反応した。反応終了後、反
応液中の溶媒及び未反応の酢酸アリルを真空蒸発で除去
した結果６６ｇの液状生成物が得られた。実施例１と同
様に構造解析した結果、生成物は原料のヒドロシリコー
ン化合物のＳｉ−Ｈ基の７０％が実施例１に示す化８に
変換した化合物であることを確認した。[Example 2] 50 g of allyl acetate (
0.50 mol), 0.2 g of a 5% isopropanol solution of chloroplatinic acid hexahydrate, and 70 g of toluene were added, and the temperature was raised to 80° C. while stirring. Next, 30.5 g (0.50 mol of Si--H groups) of a hydrosilicone compound having the structural formula shown in Chemical Formula 9 below was added dropwise into the flask over a period of 20 minutes. After the dropwise addition was completed, the reaction was carried out at 80° C. for 5 hours. After the reaction was completed, the solvent and unreacted allyl acetate in the reaction solution were removed by vacuum evaporation, resulting in 66 g of a liquid product. As a result of structural analysis in the same manner as in Example 1, it was confirmed that the product was a compound in which 70% of the Si-H groups of the hydrosilicone compound as a raw material were converted to the chemical formula 8 shown in Example 1.
【００２２】[0022]
【化９】[Chemical formula 9]
【００２３】[0023]
【応用例】実施例１，２で得られたシリコーン化合物と
メチルメタクリレート／ｎ−ブチルアクリレート／３−
メタクリロキシプロピルトリメトキシシランの３元共重
合体（モル比２／１／０．２８）を表１で示す配合で混
合し、ブリキ板上に膜厚が３０μになるように塗布した
。室温で放置するといずれも約３０分間でタックフリー
となり、７日後には完全に硬化した。表面光沢はいずれ
もすぐれていた。サンシャインウェザーメーターを用い
て２，０００時間後の耐候性（光沢保持率）を測定した
。その結果を表２に示す。この結果よりいずれも耐候性
が非常にすぐれていることを確認した。[Application example] Silicone compounds obtained in Examples 1 and 2 and methyl methacrylate/n-butyl acrylate/3-
A terpolymer of methacryloxypropyltrimethoxysilane (mole ratio 2/1/0.28) was mixed in the formulation shown in Table 1 and coated on a tin plate to a film thickness of 30 μm. When left at room temperature, all became tack-free in about 30 minutes and were completely cured after 7 days. All had excellent surface gloss. Weather resistance (gloss retention) was measured after 2,000 hours using a sunshine weather meter. The results are shown in Table 2. From these results, it was confirmed that both had excellent weather resistance.
【００２４】[0024]
【表１】[Table 1]
【００２５】[0025]
【表２】[Table 2]
【００２６】[0026]
【発明の効果】本発明のシリコーン化合物は、耐候性、
耐熱性などのすぐれた塗料、シーリング剤などの原料と
して有用である。[Effect of the invention] The silicone compound of the present invention has weather resistance,
It is useful as a raw material for paints and sealants with excellent heat resistance.
【図１】実施例１で得られた生成物の １Ｈ−ＮＭＲス
ペクトルである。FIG. 1 is a 1H-NMR spectrum of the product obtained in Example 1.
【図２】実施例１で得られた生成物の赤外吸収スペクト
ルである。FIG. 2 is an infrared absorption spectrum of the product obtained in Example 1.
Claims (2)
。 【化１】[Claim 1] A silicone compound represented by the following formula 1. [Chemical formula 1]
シリコーン化合物と醋酸アリルとを白金系触媒の存在下
、５０〜１５０℃で反応させることを特徴とするシリコ
ーン化合物の製法。 【化２】2. A method for producing a silicone compound, which comprises reacting a ladder-type hydrosilicone compound represented by the following formula 2 with allyl acetate at 50 to 150° C. in the presence of a platinum catalyst. [Case 2]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP905091A JPH04252229A (en) | 1991-01-29 | 1991-01-29 | Silicone compound and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP905091A JPH04252229A (en) | 1991-01-29 | 1991-01-29 | Silicone compound and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04252229A true JPH04252229A (en) | 1992-09-08 |
Family
ID=11709813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP905091A Withdrawn JPH04252229A (en) | 1991-01-29 | 1991-01-29 | Silicone compound and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04252229A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007121102A1 (en) * | 2006-04-14 | 2007-10-25 | 3M Innovative Properties Company | Curable composition containing fluoroalkyl hydrosilicone |
| US7407710B2 (en) | 2006-04-14 | 2008-08-05 | 3M Innovative Properties Company | Composition containing fluoroalkyl silicone and hydrosilicone |
| US7413807B2 (en) | 2006-04-14 | 2008-08-19 | 3M Innovative Properties Company | Fluoroalkyl silicone composition |
| JP5050310B2 (en) * | 2000-03-31 | 2012-10-17 | 日立化成工業株式会社 | Method for producing novel silicone polymer, silicone polymer produced by the method, thermosetting resin composition, resin film, metal foil with insulating material, insulating film with double-sided metal foil, metal-clad laminate, multilayer metal-clad Laminated board and multilayer printed wiring board |
| EP2817428B1 (en) | 2012-02-20 | 2016-04-20 | Tata Steel Nederland Technology B.V. | High strength bake-hardenable low density steel and method for producing said steel |
-
1991
- 1991-01-29 JP JP905091A patent/JPH04252229A/en not_active Withdrawn
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5050310B2 (en) * | 2000-03-31 | 2012-10-17 | 日立化成工業株式会社 | Method for producing novel silicone polymer, silicone polymer produced by the method, thermosetting resin composition, resin film, metal foil with insulating material, insulating film with double-sided metal foil, metal-clad laminate, multilayer metal-clad Laminated board and multilayer printed wiring board |
| WO2007121102A1 (en) * | 2006-04-14 | 2007-10-25 | 3M Innovative Properties Company | Curable composition containing fluoroalkyl hydrosilicone |
| US7407710B2 (en) | 2006-04-14 | 2008-08-05 | 3M Innovative Properties Company | Composition containing fluoroalkyl silicone and hydrosilicone |
| US7410704B2 (en) | 2006-04-14 | 2008-08-12 | 3M Innovative Properties Company | Composition containing fluoroalkyl hydrosilicone |
| US7413807B2 (en) | 2006-04-14 | 2008-08-19 | 3M Innovative Properties Company | Fluoroalkyl silicone composition |
| EP2817428B1 (en) | 2012-02-20 | 2016-04-20 | Tata Steel Nederland Technology B.V. | High strength bake-hardenable low density steel and method for producing said steel |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A300 | Application deemed to be withdrawn because no request for examination was validly filed |
Free format text: JAPANESE INTERMEDIATE CODE: A300 Effective date: 19980514 |