JPH1017577A - Alkoxysilyl modified propionic acid ester - Google Patents
Alkoxysilyl modified propionic acid esterInfo
- Publication number
- JPH1017577A JPH1017577A JP8195692A JP19569296A JPH1017577A JP H1017577 A JPH1017577 A JP H1017577A JP 8195692 A JP8195692 A JP 8195692A JP 19569296 A JP19569296 A JP 19569296A JP H1017577 A JPH1017577 A JP H1017577A
- Authority
- JP
- Japan
- Prior art keywords
- agent
- hydroxyl group
- acid ester
- propionic acid
- 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.)
- Granted
Links
- 125000005370 alkoxysilyl group Chemical group 0.000 title abstract 3
- 150000003151 propanoic acid esters Chemical class 0.000 title abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 15
- 239000000203 mixture Substances 0.000 abstract description 15
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 12
- 239000002516 radical scavenger Substances 0.000 abstract description 9
- 229920002379 silicone rubber Polymers 0.000 abstract description 9
- 239000004945 silicone rubber Substances 0.000 abstract description 9
- 239000003054 catalyst Substances 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 229910052751 metal Inorganic materials 0.000 abstract description 6
- 239000002184 metal Substances 0.000 abstract description 6
- 229910052697 platinum Inorganic materials 0.000 abstract description 6
- 239000000377 silicon dioxide Substances 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 5
- 238000003860 storage Methods 0.000 abstract description 5
- 239000003381 stabilizer Substances 0.000 abstract description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 3
- 238000007259 addition reaction Methods 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 239000012756 surface treatment agent Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- -1 acryl group Chemical group 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 description 1
- RMKZLFMHXZAGTM-UHFFFAOYSA-N [dimethoxy(propyl)silyl]oxymethyl prop-2-enoate Chemical compound CCC[Si](OC)(OC)OCOC(=O)C=C RMKZLFMHXZAGTM-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 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
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 1
- YTPNLBCMTSWLKJ-UHFFFAOYSA-N dimethoxy-methyl-prop-1-en-2-yloxysilane Chemical compound CO[Si](C)(OC)OC(C)=C YTPNLBCMTSWLKJ-UHFFFAOYSA-N 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 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
- 239000000565 sealant Substances 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、新規なアルコキシ
シリル変性プロピオン酸エステルに関し、特にアルコキ
シシリル化剤、シリカの表面処理剤、硬化剤、ヒドロキ
シル基スカベンジャー等として有用な該エステルに関す
る。The present invention relates to a novel alkoxysilyl-modified propionate, and more particularly to an ester useful as an alkoxysilylation agent, a silica surface treatment agent, a curing agent, a hydroxyl group scavenger, and the like.
【０００２】[0002]
【従来の技術】従来、建物のシーラント、電気・電子部
品のポッティング材等には、外気中の湿気と反応して硬
化する室温硬化型組成物が使用されており、中でも、室
温硬化型シリコーンゴム組成物が、耐侯性、耐熱性等の
点で優れている。特に、アルコキシシランを硬化剤とし
て用いる脱アルコールタイプのシリコーンゴム組成物
が、無臭、各種金属を犯さない等の点から、その需要を
伸ばしつつある。しかし、脱アルコールタイプのシリコ
ーンゴム組成物は、一液型に調製されると、時間の経過
とともに組成物の硬化性が失われるという欠点を有す
る。そこで、シラノール又はアルコキシ末端停止オルガ
ノポリシロキサン、アルコキシシラン、縮合触媒及び酢
酸イソプロペニル、メチルジメトキシイソプロペノキシ
シラン等のヒドロキシル基スカベンジャーからなるシリ
コーンゴム組成物が、特開昭５９−２１３７６２号公報
等に開示され、このヒドロキシル基スカベンジャーの添
加により、シリコーンゴム組成物の密封条件下の保存性
が改善されている。2. Description of the Related Art Conventionally, room temperature-curable compositions which cure by reacting with moisture in the outside air have been used as sealants for buildings and potting materials for electric and electronic parts. The composition is excellent in terms of weather resistance, heat resistance and the like. In particular, the demand for a dealcohol-type silicone rubber composition using an alkoxysilane as a curing agent has been increasing in terms of odorlessness and prevention of various metals. However, dealcoholized silicone rubber compositions have the disadvantage that, once prepared in a one-pack type, the curability of the composition is lost over time. Therefore, a silicone rubber composition comprising a silanol or alkoxy-terminated organopolysiloxane, an alkoxysilane, a condensation catalyst and a hydroxyl group scavenger such as isopropenyl acetate or methyldimethoxyisopropenoxysilane is disclosed in JP-A-59-213762. Disclosed is that the addition of the hydroxyl scavenger improves the storage stability of the silicone rubber composition under sealed conditions.
【０００３】[0003]
【発明が解決しようとする課題】しかし、上記のヒドロ
キシル基スカベンジャーは、シラノール末端停止オルガ
ノポリシロキサン又はアルコールのヒドロキシル基と反
応する際に、アミン等の金属腐食性ガスを放出したり、
組成物の反応に関与しない化合物を生成し、その結果、
組成物の硬化性を阻害したりするという問題がある。そ
こで、本発明の課題は、 ヒドロキシル基に対して反応活
性を有するα−シリルエステルであって、 ヒドロキシル
基と反応する際に生成するエステルが硬化剤にもなり得
るα−シリルエステルを提供することにある。However, the above-mentioned hydroxyl group scavenger releases a metal corrosive gas such as an amine when reacting with a hydroxyl group of a silanol-terminated organopolysiloxane or alcohol,
Produce compounds that do not participate in the reaction of the composition,
There is a problem that the curability of the composition is inhibited. Accordingly, an object of the present invention is to provide an α-silyl ester having a reaction activity with respect to a hydroxyl group, wherein the ester generated when reacting with the hydroxyl group can also serve as a curing agent. It is in.
【０００４】[0004]
【発明を解決するための手段】本発明者らは、上記の課
題を克服するために検討を重ねた結果、今回の発明に到
達した。本発明によれば、一般式(1) ：Means for Solving the Problems The inventors of the present invention have conducted various studies to overcome the above-mentioned problems, and as a result, have reached the present invention. According to the present invention, general formula (1):
【０００５】[0005]
【化２】 Embedded image
【０００６】〔式中、Ｒ1 は独立に低級アルキル基であ
り、Ｒ2 は低級アルキレン基であり、ｍ及びｎは独立に
２又は３である〕で示されるアルコキシシリル変性プロ
ピオン酸エステルが提供される。Wherein R 1 is independently a lower alkyl group, R 2 is a lower alkylene group, and m and n are each independently 2 or 3, and the alkoxysilyl-modified propionate represented by the formula: Is done.
【０００７】[0007]
【発明の実施の形態】アルコキシシリル変性プロピオン酸エステル 一般式(1) において、Ｒ1 で示される低級アルキル基と
しては、 メチル基、エチル基等の炭素原子数１〜４のア
ルキル基が好ましく、特に好ましくはメチル基である。
また、複数のＲ1 は、互いに同一であっても異なってい
てもよい。Ｒ2 で示される低級アルキレン基としては、
メチレン基、エチレン基、プロピレン基等の炭素原子数
１〜３のアルキレン基が好ましく、特にプロピレン基が
好ましい。また、ｍ及びｎは、独立に２又は３である。BEST MODE FOR CARRYING OUT THE INVENTION In the alkoxysilyl-modified propionate general formula (1), the lower alkyl group represented by R 1 is preferably an alkyl group having 1 to 4 carbon atoms such as a methyl group and an ethyl group. Particularly preferred is a methyl group.
A plurality of R 1 may be the same or different from each other. As the lower alkylene group represented by R 2 ,
An alkylene group having 1 to 3 carbon atoms such as a methylene group, an ethylene group and a propylene group is preferred, and a propylene group is particularly preferred. Further, m and n are independently 2 or 3.
【０００８】したがって、一般式(1) で示されるアルコ
キシシリル変性プロピオン酸エステルの好ましい例とし
ては、 一般式(2) ：Accordingly, preferred examples of the alkoxysilyl-modified propionate represented by the general formula (1) include the general formula (2):
【０００９】[0009]
【化３】 Embedded image
【００１０】〔式中、ｍ及びｎは前記と同じ意味であ
る〕で示されるものが挙げられる。本発明のアルコキシ
シリル変性プロピオン酸エステルの具体例としては、下
記のものが挙げられる。[Wherein, m and n have the same meanings as described above]. The following are specific examples of the alkoxysilyl-modified propionate of the present invention.
【００１１】[0011]
【化４】 Embedded image
【００１２】製造方法 本発明の一般式(1) で示されるアルコキシシリル変性プ
ロピオン酸エステルは、例えば式(3) ： Production Method The alkoxysilyl-modified propionate represented by the general formula (1) of the present invention can be prepared, for example, by the following method:
【００１３】[0013]
【化５】 Embedded image
【００１４】〔式中、Ｒ1 、Ｒ2 、ｍ及びｎは前記と同
じ意味である〕で示されるように、ヒドロシリル基含有
アルコキシランとアクリル基含有アルコキシシランと
を、ヒドロシリル付加反応させることにより得られる。
ここで、アクリル基含有アルコキシシランとヒドロシリ
ル基含有アルコキシランとの反応モル比は、通常、0.8
／１〜1.2 ／１である。上記の反応は、通常、触媒の存
在下で行われる。該触媒としては、ヒドロシリル付加反
応に従来公知の白金族金属系触媒、例えば白金系、パラ
ジウム系及びロジウム系のものが挙げられ、白金系のも
のが好適である。白金系金属触媒としては、白金黒；ア
ルミナ、シリカ等の担体に固体白金を担持させたもの；
塩化白金酸、アルコール変性塩化白金酸、塩化白金酸と
オレフィンとの錯体；白金とビニルシロキサンとの錯体
等が挙げられる。これらの使用量は、いわゆる触媒量で
よく、前記アクリル基含有アルコキシシランとヒドロシ
リル基含有アルコキシシランとの合計量に対して、白金
族金属換算で、通常、0.1 〜1000ｐｐｍ、好ましくは１
〜100 ｐｐｍの量である。上記反応の温度は、通常、室
温〜200 ℃の温度でよく、好ましくは30〜120 ℃の範囲
である。反応時間は、製造規模及び反応温度に応じて適
宜決められばよい。上記反応において、溶媒を使用しな
くともよく、また、必要に応じて反応に悪影響を与えな
い溶媒を使用してもよい。In the formula, R 1 , R 2 , m and n have the same meanings as described above, and the hydrosilyl group-containing alkoxysilane and the acryl group-containing alkoxysilane are subjected to a hydrosilyl addition reaction. can get.
Here, the reaction molar ratio of the acrylic group-containing alkoxysilane and the hydrosilyl group-containing alkoxylan is usually 0.8
/ 1 to 1.2 / 1. The above reaction is usually performed in the presence of a catalyst. Examples of the catalyst include platinum group metal-based catalysts conventionally known for hydrosilyl addition reaction, such as platinum-based, palladium-based and rhodium-based catalysts, and platinum-based catalysts are preferred. Platinum-based metal catalysts include platinum black; solid platinum supported on a carrier such as alumina or silica;
Chloroplatinic acid; alcohol-modified chloroplatinic acid; complexes of chloroplatinic acid with olefins; complexes of platinum with vinylsiloxane; These may be used in a so-called catalytic amount, which is usually 0.1 to 1000 ppm, preferably 1 to 1,000 ppm in terms of platinum group metal, based on the total amount of the acrylic group-containing alkoxysilane and the hydrosilyl group-containing alkoxysilane.
In the amount of ｐｐｍ100 ppm. The temperature of the above reaction may be generally from room temperature to 200 ° C, preferably from 30 to 120 ° C. The reaction time may be appropriately determined according to the production scale and the reaction temperature. In the above reaction, a solvent need not be used, and a solvent that does not adversely affect the reaction may be used as necessary.
【００１５】上記式(3) の反応では、本発明のアルコキ
シシリル変性プロピオン酸エステルのほかに、副生物と
して一般式(4) 〜(5) ：In the reaction of the above formula (3), in addition to the alkoxysilyl-modified propionate of the present invention, by-products represented by the following general formulas (4) to (5):
【００１６】[0016]
【化６】 Embedded image
【００１７】〔式中、Ｒ1 、Ｒ2 、ｍ及びｎは前記と同
じ意味である〕で表される異性体が、若干量生成するこ
とがある。これらの副生物は、必要に応じて蒸留等の精
製手段により除去してもよい。また、本発明のアルコキ
シシリル変性プロピオン酸エステルを、保存安定剤、硬
化剤等として使用する場合には、該副生物がこれらの特
性に悪影響を与えないので分離しなくてもよい。[Wherein, R 1 , R 2 , m and n have the same meanings as described above] may be formed in a small amount. These by-products may be removed by a purification means such as distillation as needed. When the alkoxysilyl-modified propionate of the present invention is used as a storage stabilizer, a curing agent, or the like, the by-products do not adversely affect these properties, so that they need not be separated.
【００１８】本発明のアルコキシシリル変性プロピオン
酸エステルは、アルコール又はシラノールのヒドロキシ
ル基と効率よく反応するため、脱アルコールタイプの室
温硬化型シリコーンゴム組成物のヒドロキシル基スカベ
ンジャーとして作用する。したがって、該化合物は、該
シリコーンゴム組成物の保存安定剤として有用であり、
その際に生成されるエステル及びアルコキシシシラン
は、硬化剤にもなり得る。また、別の用途として、α，
ω−ジヒドロキシ−ジメチルポリシロキサン等の末端ア
ルコキシシリル化剤、シリカの表面処理剤等も期待され
る。The alkoxysilyl-modified propionate of the present invention efficiently reacts with the hydroxyl group of alcohol or silanol, and thus acts as a hydroxyl group scavenger of a dealcoholized room temperature-curable silicone rubber composition. Therefore, the compound is useful as a storage stabilizer for the silicone rubber composition,
The esters and alkoxysilanes formed at that time can also serve as curing agents. As another application, α,
A terminal alkoxy silylation agent such as ω-dihydroxy-dimethylpolysiloxane, a surface treatment agent for silica, and the like are also expected.
【００１９】[0019]
【実施例】以下、本発明を実施例により説明する。 〔実施例１〕攪拌機、還流冷却管、温度計及び滴下ロー
トを備えた１リットルの４つ口フラスコに、 メチルジメトキシシラン １７５．２ｇ（１．６５モル）、 塩化白金酸（Ｈ2 ＰｔＣｌ6 ・Ｈ2 ０） ０．１０ｇ、 重合禁止剤としてイルガノックス１３３０（商品名：チバ・ガイギー社製） ０．３ｇ、及び 2,6-ジ-t- ブチル-4- メチルフェノール ０．３ｇ を入れ、攪拌しながら温度を４０℃に上げた。次いで、
該混合物に、アクリロキシプロピルトリメトキシシラン
３５１ｇ（１．５モル）を攪拌下で滴下した。発熱によ
り、５０℃の温度に上昇したところで、この温度に３時
間保持した。反応終了後、減圧蒸留により沸点１３０〜
１３５℃／２ｍｍＨｇに、３１１ｇ（収率６０％）の生
成物が得られた。ガスクロマトグラフィ−、 1Ｈ−ＮＭ
Ｒ及びＩＲ分析の結果、該生成物には、式(6) ：The present invention will be described below with reference to examples. [Example 1] 175.2 g (1.65 mol) of methyldimethoxysilane, chloroplatinic acid (H 2 PtCl 6. 0.10 g of H 2 0), 0.3 g of Irganox 1330 (trade name, manufactured by Ciba-Geigy) as a polymerization inhibitor, and 0.3 g of 2,6-di-t-butyl-4-methylphenol were added. The temperature was increased to 40 ° C. with stirring. Then
To this mixture, 351 g (1.5 mol) of acryloxypropyltrimethoxysilane was added dropwise with stirring. When the temperature rose to 50 ° C. due to heat generation, the temperature was maintained for 3 hours. After the completion of the reaction, a boiling point of 130 to
At 135 ° C./2 mmHg, 311 g (yield 60%) of the product was obtained. Gas chromatography, 1 H-NM
As a result of R and IR analysis, the product was represented by the formula (6):
【００２０】[0020]
【化７】 Embedded image
【００２１】で示されるアルコキシシリル変性プロピオ
ン酸エステル(a) 、及び副生物として式(7):An alkoxysilyl-modified propionate (a) represented by the formula: and a by-product of the formula (7):
【００２２】[0022]
【化８】 Embedded image
【００２３】で示される異性体(b) が、ａ：ｂ＝９５：
５の重量比で含有されていることが判明した。ＧＣ・Ｗ
Ｓ分析及び 1Ｈ−ＮＭＲ分析の結果を以下に示す。ＧＣ・ＷＳ分析 ｍ／ｅ：３４０（分子量３４０） 1Ｈ−ＮＭＲ分析 δ（ｐｐｍ） ０．１２ （ｓ，３Ｈ，Ｓｉ−ＣＨ3 ） ０．１５ （ｑ，１Ｈ，Ｃ−Ｈ） ０．４０ （ｔ，２Ｈ，−ＣＨ2 −） １．３〜１．７ （ｂｒｏａｄ，２Ｈ，−ＣＨ2 −） １．５０ （ｄ，３Ｈ，−Ｃ−ＣＨ3 ） ３．４８ （ｓ，９Ｈ，−ＯＣＨ3 ） ３．５０ （ｓ，６Ｈ，−ＯＣＨ3 ） ３．４〜３．９ （ｔ，２Ｈ，−ＣＨ2 −） 上記で得られた生成物の 1Ｈ−ＮＭＲスペクトル及びＩ
Ｒスペクトルを、それぞれ、図１及び図２に示す。な
お、図１中のａ〜ｈの帰属は以下である。 Isomer (b) represented by the formula: a: b = 95:
It was found to be contained at a weight ratio of 5. GC ・ W
The results of S analysis and 1 H-NMR analysis are shown below. GC / WS analysis m / e: 340 (molecular weight 340) 1 H-NMR analysis δ (ppm) 0.12 (s, 3H, Si-CH 3 ) 0.15 (q, 1H, C- H ) 0. 40 (t, 2H, -C H 2 -) 1.3~1.7 (broad, 2H, -C H 2 -) 1.50 (d, 3H, -C- CH 3) 3.48 (s, 9H, -OC H 3) 3.50 ( s, 6H, -OC H 3) 3.4~3.9 (t, 2H, -C H 2 -) 1 H-NMR of the product obtained above Spectrum and I
The R spectrum is shown in FIGS. 1 and 2, respectively. The assignments of a to h in FIG. 1 are as follows.
【００２４】[0024]
【発明の効果】本発明によれば、新規なアルコキシシリ
ル変性プロピオン酸エステルが得られる。該化合物は、
脱アルコールタイプの室温硬化型シリコーンゴム組成物
のヒドロキシル基スカベンジャーとしての保存安定剤に
有用である。その際、生成するエステル及びアルコキシ
シシランは、ともに硬化剤になるため、反応に関与しな
い化合物を生成しないという点で、従来のヒドロキシル
基スカベンジャーより優れている。また、該化合物は、
α，ω−ジヒドロキシジメチルポリシロキサン等の末端
アルコキシシリル化剤、シリカの表面処理剤等の用途も
期待される。According to the present invention, a novel alkoxysilyl-modified propionate can be obtained. The compound is
It is useful as a storage stabilizer as a hydroxyl group scavenger in a dealcoholized room temperature-curable silicone rubber composition. At this time, the generated ester and alkoxysilane are both curing agents, and therefore are superior to the conventional hydroxyl group scavenger in that they do not generate compounds that do not participate in the reaction. Also, the compound
Applications such as terminal alkoxysilylating agents such as α, ω-dihydroxydimethylpolysiloxane and silica surface treatment agents are also expected.
【図１】実施例１で得られた生成物のＮＭＲスペクトル
である。FIG. 1 is an NMR spectrum of a product obtained in Example 1.
【図２】実施例１で得られた生成物のＩＲスペクトルで
ある。FIG. 2 is an IR spectrum of the product obtained in Example 1.
Claims (2)
級アルキレン基であり、ｍ及びｎは独立に２又は３であ
る〕で示されるアルコキシシリル変性プロピオン酸エス
テル。[Claim 1] General formula (1): [Wherein R 1 is independently a lower alkyl group, R 2 is a lower alkylene group, and m and n are independently 2 or 3].
基である、請求項１に記載のアルコキシシリル変性プロ
ピオン酸エステル。2. The alkoxysilyl-modified propionate according to claim 1, wherein R 1 is a methyl group and R 2 is a propylene group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19569296A JP3415999B2 (en) | 1996-07-05 | 1996-07-05 | Alkoxysilyl-modified propionate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19569296A JP3415999B2 (en) | 1996-07-05 | 1996-07-05 | Alkoxysilyl-modified propionate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH1017577A true JPH1017577A (en) | 1998-01-20 |
| JP3415999B2 JP3415999B2 (en) | 2003-06-09 |
Family
ID=16345417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19569296A Expired - Fee Related JP3415999B2 (en) | 1996-07-05 | 1996-07-05 | Alkoxysilyl-modified propionate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3415999B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2021206064A1 (en) * | 2020-04-06 | 2021-10-14 |
-
1996
- 1996-07-05 JP JP19569296A patent/JP3415999B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP3415999B2 (en) | 2003-06-09 |
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