JP7126999B2 - Alkynyl group-containing cyclic organopolysiloxane and hydrosilylation reaction control agent - Google Patents
Alkynyl group-containing cyclic organopolysiloxane and hydrosilylation reaction control agent Download PDFInfo
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Description
本発明は、ヒドロシリル化反応制御剤として有用な新規アルキニル基含有オルガノポリシロキサンに関する。 The present invention relates to novel alkynyl group-containing organopolysiloxanes useful as hydrosilylation reaction control agents.
脂肪族不飽和結合とヒドロシリル基の白金触媒による付加反応は多くの分野で応用されており、特にシリコーン工業の分野では付加反応型レジンやゴムの架橋の手段として広く応用されている。 Platinum-catalyzed addition reactions between aliphatic unsaturated bonds and hydrosilyl groups are applied in many fields, and in the field of silicone industry in particular, it is widely used as a means of cross-linking addition reaction type resins and rubbers.
このようなヒドロシリル化反応を応用した付加反応型シリコーン樹脂組成物は室温でも反応が進行するため、一般に硬化速度の調整や保存安定性の向上を目的に反応制御剤が添加されている。反応制御剤としては、例えば1-エチニル-1-シクロヘキサノール、2-メチル-3-ブチン-2-オール、2,5-ジメチル-3-ヘキシン-2,5-ジオール、3-メチル-1-ペンタデシン-3-オール(特許文献1)といったアセチレンアルコール類などが用いられている。 Since the reaction proceeds even at room temperature in addition reaction-type silicone resin compositions that apply such hydrosilylation reactions, reaction inhibitors are generally added for the purpose of adjusting the curing speed and improving storage stability. Examples of reaction controllers include 1-ethynyl-1-cyclohexanol, 2-methyl-3-butyn-2-ol, 2,5-dimethyl-3-hexyne-2,5-diol, 3-methyl-1- Acetylene alcohols such as pentadecyn-3-ol (Patent Document 1) are used.
しかし、上記アセチレンアルコール類は炭化水素骨格のみで構成されているため、ヒドロシリル化制御剤として樹脂組成物に添加した場合、硬化後の信頼性試験において樹脂が着色するという問題がある。 However, since the above acetylene alcohols are composed only of a hydrocarbon skeleton, there is a problem that when they are added to a resin composition as a hydrosilylation control agent, the resin is colored in a reliability test after curing.
この対策として、例えば特許文献2には、下記式、
で示されるアセチレン性不飽和基を有するアルコキシ基で変性されたオルガノシロキサンを反応制御剤として用いることが記載されている。
As a countermeasure against this, for example, in Patent Document 2, the following formula,
It is described that an organosiloxane modified with an alkoxy group having an acetylenically unsaturated group represented by is used as a reaction control agent.
しかし、前記特許文献2記載の直鎖状オルガノシロキサンでは、アセチレン基を隣接させることが難しく、十分な反応抑制効果が得られない場合がある。また、硬化物に透明性を求められるような用途など、硬化前には十分な反応制御能を有し、且つ、硬化後は硬化物の着色を抑えることができるような反応制御剤の開発が求められていた。 However, in the straight-chain organosiloxane described in Patent Document 2, it is difficult to place the acetylene groups adjacent to each other, and a sufficient reaction suppressing effect may not be obtained. In addition, for applications that require transparency in the cured product, development of a reaction control agent that has sufficient reaction control ability before curing and can suppress coloring of the cured product after curing is being developed. was wanted.
本発明は、上記問題に鑑みてなされたものであり、付加硬化型オルガノポリシロキサン樹脂組成物においてヒドロシリル化反応抑制剤として機能することができ、硬化後の耐変色性に優れる組成物を与える、アルキニル基含有オルガノポリシロキサンを提供することを目的とする。 The present invention has been made in view of the above problems, and provides a composition that can function as a hydrosilylation reaction inhibitor in an addition-curable organopolysiloxane resin composition and has excellent discoloration resistance after curing. An object of the present invention is to provide an alkynyl group-containing organopolysiloxane.
本発明は上記課題を達成すべく、検討したところ、下記式(1)で表される、アルキニル基を少なくとも1つ有する環状オルガノポリシロキサンを合成し、該オルガノポリシロキサンが上記課題を解決できることを見出し、本発明をなすに至った。 In order to achieve the above objects, the present invention was investigated, and found that a cyclic organopolysiloxane having at least one alkynyl group represented by the following formula (1) was synthesized and that the organopolysiloxane could solve the above objects. This discovery led to the present invention.
即ち、本発明は下記式(1)で示されるアルキニル基含有環状オルガノポリシロキサンからなるヒドロシリル化反応制御剤を提供する。
That is, the present invention provides a hydrosilylation reaction controller comprising an alkynyl group-containing cyclic organopolysiloxane represented by the following formula (1).
本発明のアルキニル基含有環状オルガノポリシロキサンをヒドロシリル化反応制御剤として含む付加反応硬化型シリコーン組成物は、耐熱・耐湿試験等の信頼性試験において耐変色性に優れる硬化物を与えることができる。更には、室温での保存安定性に優れる組成物を提供することもできる。 The addition reaction-curable silicone composition containing the alkynyl group-containing cyclic organopolysiloxane of the present invention as a hydrosilylation reaction inhibitor can give a cured product with excellent discoloration resistance in reliability tests such as heat and moisture resistance tests. Furthermore, it is also possible to provide a composition having excellent storage stability at room temperature.
以下、本発明をより詳細に説明する。
本発明は、下記式(1)で示されるアルキニル基含有環状オルガノポリシロキサンである。
The present invention is an alkynyl group-containing cyclic organopolysiloxane represented by the following formula (1).
R1は、互いに独立に、炭素数1~6の飽和脂肪族炭化水素基、または炭素数6~12の芳香族炭化水素基であり、好ましくは炭素数1~3の飽和脂肪族炭化水素基、炭素数6~8の芳香族炭化水素基から選ばれる基である。飽和脂肪族炭化水素基としては、メチル基、エチル基、プロピル基、及びブチル基等のアルキル基;シクロペンチル基、及びシクロヘキシル基等のシクロアルキル基、などが挙げられる。これらの中でも、メチル基が好ましい。芳香族炭化水素基の例としては、フェニル基、トリル基、ナフチル基、及びビフェニル基等のアリール基や、ベンジル基、フェニルエチル基、及びフェニルプロピル基等のアラルキル基などが挙げられる。これらの中でも、フェニル基が好ましい。R1として最も好ましくはメチル基である。 Each R 1 is independently a saturated aliphatic hydrocarbon group having 1 to 6 carbon atoms or an aromatic hydrocarbon group having 6 to 12 carbon atoms, preferably a saturated aliphatic hydrocarbon group having 1 to 3 carbon atoms. , an aromatic hydrocarbon group having 6 to 8 carbon atoms. Examples of saturated aliphatic hydrocarbon groups include alkyl groups such as methyl group, ethyl group, propyl group and butyl group; cycloalkyl groups such as cyclopentyl group and cyclohexyl group; Among these, a methyl group is preferred. Examples of aromatic hydrocarbon groups include aryl groups such as phenyl group, tolyl group, naphthyl group and biphenyl group, and aralkyl groups such as benzyl group, phenylethyl group and phenylpropyl group. Among these, a phenyl group is preferred. R 1 is most preferably a methyl group.
R2は、互いに独立に、水素原子又は前記式(A)で表される基であり、ただし、R2のうち少なくとも1つは前記式(A)で表される基である。式(A)において、aは0~6の整数であり、好ましくは0~3の整数である。 Each R 2 is independently a hydrogen atom or a group represented by formula (A) above, provided that at least one of R 2 is a group represented by formula (A) above. In formula (A), a is an integer of 0-6, preferably an integer of 0-3.
R3は互いに独立に、水素原子または炭素数1~6の飽和脂肪族炭化水素基であり、好ましくは水素原子または炭素数1~3の飽和脂肪族炭化水素基である。飽和脂肪族炭化水素基としては、メチル基、エチル基、プロピル基、及びブチル基等のアルキル基;シクロペンチル基、及びシクロヘキシル基等のシクロアルキル基、などが挙げられる。これらの中でも、R3はメチル基が好ましく、全てのR3がメチル基であるのが最も好ましい。R3がメチル基であることにより、アセチレン基のキレート作用による付加反応抑制効果をより向上することができ、保存安定性に優れる組成物を与えることができる。 Each R 3 is independently a hydrogen atom or a saturated aliphatic hydrocarbon group having 1 to 6 carbon atoms, preferably a hydrogen atom or a saturated aliphatic hydrocarbon group having 1 to 3 carbon atoms. Examples of saturated aliphatic hydrocarbon groups include alkyl groups such as methyl group, ethyl group, propyl group and butyl group; cycloalkyl groups such as cyclopentyl group and cyclohexyl group; Among these, R 3 is preferably a methyl group, and most preferably all R 3 are methyl groups. When R 3 is a methyl group, the effect of suppressing the addition reaction due to the chelating action of the acetylene group can be further improved, and a composition having excellent storage stability can be obtained.
上記式(1)においてnはシロキサン単位の数である。該nは3~6の整数であり、好ましくは3~5の整数である。好ましくは、R2で示される基のうち1以上、好ましくは2以上が上記式(A)で表されるアルキニル基含有有機基であり、且つ、少なくとも1のR2は水素原子であるのがよい。 In the above formula (1), n is the number of siloxane units. Said n is an integer of 3-6, preferably an integer of 3-5. Preferably, one or more, preferably two or more of the groups represented by R 2 are alkynyl group-containing organic groups represented by the above formula (A), and at least one R 2 is a hydrogen atom. good.
好ましくは、前記式(A)において、a=0であり、R3が水素原子又はメチル基であるのがよく、最も好ましくは下記式(a)又は(b)で表されるアルキニル基含有有機基であり、保存安定性の観点より最も好ましくは下記式(b)で表される基である。
上記式(1)で表されるアルキニル基含有環状オルガノポリシロキサンとしては、例えば、下記式で表される化合物があげられる。
[アルキニル基含有オルガノポリシロキサンの製造方法]
本発明のアルキニル基含有環状オルガノポリシロキサンは、例えば、トリスペンタフルオロボラン等の触媒存在下に、アセチレンアルコールとヒドロシリル基含有環状オルガノシロキサンとを脱水素反応させることにより製造することができる。ボラン触媒を用いた上記脱水素反応による製造方法では、オルガノポリシロキサン鎖の望まない分子量の増大を防ぐことができ、目的とするアルキニル基含有環状オルガノポリシロキサンを高収率で得られるため望ましい。脱水素反応の条件は、適宜調整されればよい。例えば、ヒドロシリル基とアセチレンアルコールとの反応比はmol比で1:1.1である。
[Method for Producing Alkynyl Group-Containing Organopolysiloxane]
The alkynyl group-containing cyclic organopolysiloxane of the present invention can be produced, for example, by dehydrogenating acetylene alcohol and hydrosilyl group-containing cyclic organosiloxane in the presence of a catalyst such as trispentafluoroborane. The production method using the dehydrogenation reaction using a borane catalyst is desirable because it can prevent an unwanted increase in the molecular weight of the organopolysiloxane chain and yield the target alkynyl group-containing cyclic organopolysiloxane in high yield. Conditions for the dehydrogenation reaction may be adjusted as appropriate. For example, the reaction ratio of hydrosilyl groups and acetylene alcohol is 1:1.1 in terms of molar ratio.
上記、アルキニル基含有オルガノポリシロキサンは、ヒドロシリル化反応の反応制御剤として優れた効果を発揮することができる。該アルキニル基含有オルガノポリシロキサンを反応制御剤として使用する際には、付加反応硬化型シリコーン組成物に含まれるアルケニル基含有オルガノポリシロキサン100質量部に対し、0.001~5質量部であることが好ましく、0.01~3質量部であることがより好ましい。付加反応硬化型シリコーン組成物の組成は特に制限されるものでない。 The alkynyl group-containing organopolysiloxane can exhibit excellent effects as a reaction control agent for the hydrosilylation reaction. When the alkynyl group-containing organopolysiloxane is used as a reaction controller, it should be 0.001 to 5 parts by mass per 100 parts by mass of the alkenyl group-containing organopolysiloxane contained in the addition reaction curing silicone composition. is preferred, and 0.01 to 3 parts by mass is more preferred. The composition of the addition reaction-curable silicone composition is not particularly limited.
以下、実施例及び比較例を示し、本発明をより詳細に説明するが、本発明は下記の実施例に制限されるものではない。
下記実施例において、1H-NMR測定は、BRUKER社製の装置(装置名:AVANCEIII 400M)を用い、溶媒:重クロロホルム、内部標準:クロロホルムを用いて行った。
EXAMPLES The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to the following examples.
In the following examples, 1 H-NMR measurements were carried out using a BRUKER apparatus (apparatus name: AVANCE III 400M) using deuterated chloroform as solvent and chloroform as internal standard.
[実施例1]
反応容器に、トリスペンタフルオロフェニルボラン0.08g(1.7×10-4mol)、を加えトルエン12gで溶解した。これに2-プロピン-1-オールを6.1g(0.10mol)加え、70℃に昇温した。これに、1,3,5,7-テトラメチルシクロテトラシロキサン6.2g(0.02mol)を30分間かけて滴下した。滴下終了後、更に70℃で3時間加熱撹拌した。加熱終了後、室温(25℃)まで冷却し、前記トリスペンタフルオロフェニルボランを吸着除去するためにマグネシウム・アルミニウム系固溶体1g(商品名:KW-2200、協和化学工業株式会社製)を添加して1時間室温で撹拌した。加圧濾過によりKW-2200を除去し、減圧化で残存溶剤を留去し下記式(A)で表されるアルキニル基含有環状オルガノポリシロキサン(化合物1)を得た。1H-NMRチャートを図1に示す。
δ0.21-0.30(OSi(CH
3 )2)12H
δ2.42-2.44(C≡CH)4H
δ4.37-4.51(OCH
2 )8H
[Example 1]
0.08 g (1.7×10 −4 mol) of trispentafluorophenylborane was added to the reactor and dissolved in 12 g of toluene. 6.1 g (0.10 mol) of 2-propyn-1-ol was added thereto, and the temperature was raised to 70°C. To this, 6.2 g (0.02 mol) of 1,3,5,7-tetramethylcyclotetrasiloxane was added dropwise over 30 minutes. After completion of the dropwise addition, the mixture was further heated and stirred at 70° C. for 3 hours. After heating, the mixture was cooled to room temperature (25° C.), and 1 g of a magnesium-aluminum solid solution (trade name: KW-2200, manufactured by Kyowa Chemical Industry Co., Ltd.) was added to adsorb and remove the trispentafluorophenylborane. Stir at room temperature for 1 hour. KW-2200 was removed by pressure filtration, and the remaining solvent was distilled off under reduced pressure to obtain an alkynyl group-containing cyclic organopolysiloxane (compound 1) represented by the following formula (A). A 1 H-NMR chart is shown in FIG.
δ0.21-0.30( OSi ( CH3 ) 2 )12H
δ2.42−2.44(C≡C H )4H
δ 4.37-4.51 (OC H 2 ) 8H
[実施例2]
反応容器に、トリスペンタフルオロフェニルボラン0.08g(1.7×10-4mol)、を加えトルエン25gで溶解した。これに2-メチル-3-ブチン-2-オールを18.4g(0.22mol)加え、70℃に昇温した。これに、1,3,5,7-テトラメチルシクロテトラシロキサン6.6g(0.03mol)を30分間かけて滴下した。滴下終了後、更に70℃で3時間加熱撹拌した。加熱終了後、室温(25℃)まで冷却し、前記トリスペンタフルオロフェニルボランを吸着除去するためにマグネシウム・アルミニウム系固溶体1g(商品名:KW-2200、協和化学工業株式会社製)を添加して1時間室温で撹拌した。加圧濾過によりKW-2200を除去し、減圧化で残存溶剤を留去し平均構造が下記式(B)で表されるアルキニル基含有環状オルガノポリシロキサン(化合物2)を得た。1H-NMRチャートを図2に示す。
δ0.19-0.20(OSi(CH
3 )2)12H
δ1.57-1.60(C-CH
3 )18H
δ2.39-2.43(C≡CH)3H
δ4.79(SiH)1H
[Example 2]
0.08 g (1.7×10 −4 mol) of trispentafluorophenylborane was added to the reactor and dissolved in 25 g of toluene. 18.4 g (0.22 mol) of 2-methyl-3-butyn-2-ol was added thereto, and the temperature was raised to 70°C. To this, 6.6 g (0.03 mol) of 1,3,5,7-tetramethylcyclotetrasiloxane was added dropwise over 30 minutes. After completion of the dropwise addition, the mixture was further heated and stirred at 70° C. for 3 hours. After heating, the mixture was cooled to room temperature (25° C.), and 1 g of a magnesium-aluminum solid solution (trade name: KW-2200, manufactured by Kyowa Chemical Industry Co., Ltd.) was added to adsorb and remove the trispentafluorophenylborane. Stir at room temperature for 1 hour. KW-2200 was removed by pressure filtration, and the remaining solvent was distilled off under reduced pressure to obtain an alkynyl group-containing cyclic organopolysiloxane (compound 2) having an average structure represented by the following formula (B). A 1 H-NMR chart is shown in FIG.
δ0.19-0.20( OSi ( CH3 ) 2 )12H
δ 1.57-1.60 (C—C H 3 ) 18H
δ2.39−2.43(C≡C H )3H
δ4.79(SiH) 1H
[付加硬化型シリコーン樹脂組成物の調製]
[実施例3]
分子鎖両末端がビニル基で封鎖された直鎖状ジメチルポリシロキサン(粘度:5,000Pa・s、ビニル基当量0.006mol/100g)157質量部と、CH2=CH(CH3)2SiO1/2単位6.9mol%、(CH3)3SiO1/2単位37.3mol%、SiO4/2単位55.8mol%で構成されるレジン状オルガノポリシロキサン(重量平均分子量:5,200、ビニル基当量0.095mol/100g)50質量部と、平均構造式が下記式(C)で示されるオルガノハイドロジェンポリシロキサン8.1質量部を均一になるまで混合した。この混合物に、ヒドロシリル化反応制御剤として、実施例1で合成した化合物1を0.059質量部(1.29×10-4mol、アセチレン量:5.2×10-4mol)加えて混合後、1,3-ジビニルテトラメチルジシロキサン白金(0)錯体(白金含有量1.0質量%)0.2質量部を加えて混合し、シリコーン樹脂組成物を調製した。
[Example 3]
157 parts by mass of linear dimethylpolysiloxane (viscosity: 5,000 Pa s, vinyl group equivalent: 0.006 mol/100 g) having both ends of the molecular chain blocked with vinyl groups, and CH 2 =CH(CH 3 ) 2 SiO Resin - like organopolysiloxane (weight average molecular weight: 5,200 , vinyl group equivalent of 0.095 mol/100 g) and 8.1 parts by mass of an organohydrogenpolysiloxane whose average structural formula is represented by the following formula (C) were mixed until uniform. To this mixture, 0.059 parts by mass (1.29×10 −4 mol, amount of acetylene: 5.2×10 −4 mol) of compound 1 synthesized in Example 1 was added as a hydrosilylation reaction controller and mixed. After that, 0.2 parts by mass of 1,3-divinyltetramethyldisiloxane platinum (0) complex (platinum content 1.0% by mass) was added and mixed to prepare a silicone resin composition.
[実施例4]
実施例3において化合物1の代わりに、化合物2を0.084質量部(1.7×10-4mol、アセチレン量:5.2×10-4mol)用いた以外は実施例3を繰り返して、シリコーン樹脂組成物を調製した。
[Example 4]
Example 3 was repeated except that 0.084 parts by mass (1.7×10 −4 mol, acetylene amount: 5.2×10 −4 mol) of compound 2 was used instead of compound 1 in Example 3. , to prepare a silicone resin composition.
[比較例1]
実施例1において化合物1の代わりに、2-メチル-3-ブチン-2-オールを0.044質量部(5.2×10-4mol、アセチレン量:5.2×10-4mol)用いた以外は実施例3を繰り返して、シリコーン樹脂組成物を調製した。
[Comparative Example 1]
0.044 parts by mass (5.2×10 −4 mol, amount of acetylene: 5.2×10 −4 mol) of 2-methyl-3-butyn-2-ol in place of compound 1 in Example 1 Example 3 was repeated except that a silicone resin composition was prepared.
[耐変色性]
実施例3、4および比較例1で調製したシリコーン樹脂組成物を、150℃で4時間加熱成型して硬化物(10mm×15mm×5mm)を得た。これら硬化物の耐熱・耐湿性試験を135℃、85%RH条件下で30時間行った。耐熱・耐湿性試験後の硬化物の外観と全透過率の値について、初期(試験前)の外観及び全透過率と比較し、耐変色性を評価した。
耐熱・耐湿性試験には、株式会社平山製作所製の不飽和型高加速寿命試験装置(装置名:HASTEST PC-242HSR2)を用いた。また、全透過率は、株式会社日立ハイテクノロジーズ製の分光光度計(装置名:U-4100)を用いて測定した。結果を表1に示す。
[Discoloration resistance]
The silicone resin compositions prepared in Examples 3 and 4 and Comparative Example 1 were heat-molded at 150° C. for 4 hours to obtain cured products (10 mm×15 mm×5 mm). These cured products were subjected to heat and moisture resistance tests under conditions of 135° C. and 85% RH for 30 hours. The appearance and total transmittance of the cured product after the heat and moisture resistance test were compared with the initial appearance (before the test) and total transmittance to evaluate discoloration resistance.
For the heat/humidity resistance test, an unsaturated type highly accelerated life test device (device name: HASTEST PC-242HSR2) manufactured by Hirayama Seisakusho Co., Ltd. was used. Further, the total transmittance was measured using a spectrophotometer (apparatus name: U-4100) manufactured by Hitachi High-Technologies Corporation. Table 1 shows the results.
上記表1に示す通り、ヒドロシリル化反応制御剤がアセチレンアルコールである比較例1の付加反応硬化型組成物を硬化して得られる硬化物は、耐熱・耐湿性試験後に黄変してしまい、耐変色性に劣った。
これに対し、本発明のアルキニル基含有環状オルガノポリシロキサンを反応制御剤として含む付加反応硬化型組成物から得られる硬化物は耐熱・耐湿性試験前後において透明性が高い。該化合物は、光学用途に用いる付加硬化型オルガノポリシロキサン組成物の反応制御剤として特に好ましい。
As shown in Table 1 above, the cured product obtained by curing the addition reaction curable composition of Comparative Example 1, in which the hydrosilylation reaction inhibitor is acetylene alcohol, turned yellow after the heat and moisture resistance test, and was resistant to heat. Poor discoloration.
In contrast, the cured product obtained from the addition reaction curing composition containing the alkynyl group-containing cyclic organopolysiloxane of the present invention as a reaction controller has high transparency before and after the heat and moisture resistance test. The compound is particularly preferred as a reaction controller for addition-curable organopolysiloxane compositions used for optical applications.
[保存安定性]
実施例4および比較例1で調製したシリコーン樹脂組成物の23℃における粘度を、調製直後、4時間後、7時間後に測定し、保存安定性を評価した。粘度はブルックフィールド回転粘度計を用いて測定した。結果を表2に示す。
[Storage stability]
The viscosities at 23°C of the silicone resin compositions prepared in Example 4 and Comparative Example 1 were measured immediately after, 4 hours, and 7 hours after preparation to evaluate storage stability. Viscosity was measured using a Brookfield rotational viscometer. Table 2 shows the results.
比較例1の付加反応硬化型組成物は調製後4時間でゲル化してしまった。一方、本発明のアルキニル基含有環状オルガノポリシロキサン(化合物2)を反応制御剤として含む実施例4の組成物は、調製後4時間及び7時間後において粘度の上昇が抑制され、保存安定性が極めて向上される。 The addition reaction curable composition of Comparative Example 1 gelled 4 hours after preparation. On the other hand, the composition of Example 4 containing the alkynyl group-containing cyclic organopolysiloxane (compound 2) of the present invention as a reaction control agent exhibited a suppressed increase in viscosity 4 hours and 7 hours after preparation, and had good storage stability. greatly improved.
本発明のアルキニル基含有環状オルガノポリシロキサンは、ヒドロシリル化反応の反応制御剤として優れた効果を発揮するものである。特に耐熱・耐湿性試験などの信頼性試験後の耐変色性に優れるため、LED用封止剤など耐久性や透明性が求められる用途に用いる付加硬化型オルガノポリシロキサン組成物の反応制御剤として特に有用である。 The alkynyl group-containing cyclic organopolysiloxane of the present invention exhibits excellent effects as a reaction control agent for hydrosilylation reactions. In particular, it has excellent discoloration resistance after reliability tests such as heat and moisture resistance tests, so it is used as a reaction control agent for addition-curable organopolysiloxane compositions used in applications that require durability and transparency, such as LED sealants. Especially useful.
Claims (3)
(式中、R3は互いに独立に、水素原子又は炭素数1~6の飽和脂肪族炭化水素基であり、aは0~6の整数である)。 A hydrosilylation reaction control agent comprising an alkynyl group-containing cyclic organopolysiloxane represented by the following formula (1)
(wherein R 3 are each independently a hydrogen atom or a saturated aliphatic hydrocarbon group having 1 to 6 carbon atoms, and a is an integer of 0 to 6).
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